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Electronic Supplementary Material (ESI) for CrystEngComm

This journal is The Royal Society of Chemistry 2011

Supplementary information:
Electrostatic properties of nine fluoroquinolone
antibiotics derived directly from their crystal structures
Julian J. Holstein, Christian B. H
ubschle and Birger Dittrich*

Crystallization Conditions
Structure
enoxacin 1.72 H2 O
lomefloxacin 2 H2 O HCl
nadifloxacin 0.5 H2 O
norfloxacin 2 H2 O
norfloxacin anhydrate
ofloxacin anhydrate

Solvent

Method

water
water
acetonitrile
water
methanol
acetonitrile

vapor diffusion with ethanol


vapor diffusion with acetone
slow evaporation
slow evaporation
slow evaporation
slow evaporation

Table 1: Crystallization conditions of measured fluoroquinolone solvates.

Refinement Details
For all datasets figures of merit (FOM) are given for three models.
IAM refinement with shelxl
IAM refinement with xd
invariom refinement with xd
The influence of the weighting scheme was also investigated. For the highquality datasets of ciprofloxacin, enoxacin, nadifloxacin and ofloxacin anhydrate a weighting scheme of w = 1/ 2 (Fo2 ) gave the best weighted R-factor.
A shelxl-type weighting scheme was used for the other structures. Based on
the values a and b (see equation 1) from IAM, refinement weight parameters
were manually adjusted for invariom refinement with the program drkplot,
which is implemented in the program wingx (for reference see experimental
section of paper). Weighting parameters employed in the refinements are give
in the tables below. Rather than having different min and max values, we
report the range of the residual density features as |min |+max .
w=

2 (Fo2 )

1
+ (aP )2 + bP

with P =

2Fc2 + M ax(Fo2 , 0)
3

(1)

Electronic Supplementary Material (ESI) for CrystEngComm


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Measurement

Solvate
Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

Refinement

ciprofloxacin

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

6 H2 O
P
1
100 K
0.71073
1.16
0.43
SHELX
0.0580
0.0743
0.0313
0.0391
1.064
0.96

XDIAM
0.0580
0.0743
0.0315
0.0462
1.2705
1.08

HCl
P(2)1 /c
100 K
0.7660
0.78
0.64
XDIN V

0.0205
0.0352
2.5770
0.72

SHELX
0.0564
1.5709
0.0427
0.0463
0.926
1.64

XDIAM
0.0564
1.5709
0.0420
0.0473
1.0076
1.58

XDIN V
0.001
1.50
0.0339
0.0392
0.9541
1.57

Table 2: Measurements and structure refinements of ciprofloxacin solvates 6


H2 O and HCl

Measurement

Solvate
Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

Refinement

enoxacin

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

1.7 H2 O
P21 /c
100 K
0.71073
1.02
0.49
SHELX
0.0594
0.4430
0.0414
0.0704
1.077
1.21

XDIAM
0.0594
0.4430
0.0376
0.0873
1.3574
1.07

3 H2 O
P(2)1 /c
100 K
0.71073
0.65
0.77
XDIN V

0.0276
0.0782
2.8305
0.65

SHELX
0.0526
0.3952
0.0369
0.0518
1.014
0.49

XDIAM
0.0526
0.3952
0.0346
0.0589
1.0740
0.51

Table 3: Measurements and structure refinements of enoxacin solvates 1.7 H2 O


and 3 H2 O

XDIN V
0.0400
0.0001
0.0256
0.0500
1.0829
0.30

Electronic Supplementary Material (ESI) for CrystEngComm


This journal is The Royal Society of Chemistry 2011

Measurement

Solvate
Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

Refinement

norfloxacin

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

2 H2 O
P21 /c
100 K
0.71073
0.77
0.65
SHELX
0.0767
0.8569
0.0486
0.0957
1.022
1.06

XDIAM
0.0767
0.8569
0.0445
0.1095
0.3972
1.00

P
1
100 K
1.5418
0.60
0.84
XDIN V
0.04
0.03
0.0337
0.0998
0.9315
0.84

SHELX
0.1322
2.6093
0.0992
0.1062
1.102
0.94

XDIAM
0.1322
2.6093
0.0953
0.1166
0.4654
1.14

XDIN V
0.1322
2.6093
0.0937
0.1176
0.4432
1.25

Measurement

Solvate
Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

Refinement

Table 4: Measurements and structure refinements of Norflocaxin 2 H2 O and


Norflocaxin anhydrate

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

SHELX
0.0585
0.00
0.0380
0.0669
0.956
0.54

fleroxacin

lomefloxacin

H2 O HCl
P21 /c
298K
0.71073
0.60
0.84

2 H2 O HCl
P21 /c
100 K
0.80000
0.54
0.92

XDIAM
0.0585
0.00
0.0343
0.0818
1.0105
0.48

XDIN V
0.04
0.01
0.0280
0.0756
0.9934
0.53

SHELX
0.1124
3.98
0.0706
0.0623
1.310
0.81

XDIAM

0.0694
0.0722
3.802
0.85

Table 5: Measurements and structure refinements of fleroxacin H2 O HCl and


lomefloxacin 4 H2 O HCl

XDIN V

0.0703
0.0737
3.910
0.76

Refinement

Measurement

Electronic Supplementary Material (ESI) for CrystEngComm


This journal is The Royal Society of Chemistry 2011

sparfloxacin

moxifloxacin

Solvate

3 H2 O

Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

P21 /n
298 K
1.5418
0.61
0.82

HCl 0.5 H2 O 0.5 CH3 OH


0.5 CH3 OH
P21
273 K
0.7107
0.59
0.84

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

SHELX
0.0394
1.1263
0.0517
0.0615
1.045
0.50

XDIAM
0.0394
1.1263
0.0537
0.0617
1.0954
0.54

XDIN V
0.001
0.40
0.0478
0.0562
1.3203
0.48

SHELX
0.0417
0.00
0.0472
0.0815
0.863
0.47

XDIAM
0.0417
0.00
0.0389
0.0868
0.9117
0.45

XDIN V
0.03
0.00
0.0375
0.0872
1.0154
0.44

Measurement

Solvate
Space group
Temperature
[
A]
Resolution [sin /]
Resolution [d]

Refinement

Table 6: Measurements and structure refinements of sparfloxacin 3 H2 O and


moxifloxacin HCl 0.5 H2 O 0.5 CH3 OH

weighting a
weighting b
R(F)
Rall (F)
GoFw
|min | + max

nadifloxacin

ofloxacin

0.5 H2 O
P21 /n
100 K
1.5418
0.62
0.81

C2/c
100 K
0.5608
0.78
0.64

SHELX
0.0818
2.9411
0.0572
0.0658
1.054
1.32

XDIAM
0.0818
2.9411
0.0571
0.0773
0.3517
1.34

XDIN V
0.08
1.37
0.0536
0.0747
0.4652
1.42

SHELX
0.0722
0.0722
0.0451
0.0594
1.016
1.048

XDIAM
0.0722
3.3730
0.0458
0.0810
0.7823
1.08

Table 7: Measurements and structure refinements of nadifloxacin 0.5 H2 O and


ofloxacin anhydrate

Aspherical scattering factors


Invariom names of scattering factors employed in invariom refinements of twelve
fluoroquinolone structures are given below together with corresponding model
compounds. Fluoroquinolone structures are sorted alphabetically.

XDIN V

0.0346
0.0701
2.7286
0.72

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Table 8: Aspherical atomic scattering factors for ciprofloxacin 6 H2 O. Invariom


names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
F(15)
O(12)
O(13)
O(14)
O(2)
O(3)
O(4)
O(5)
O(6)
O(7)
N(1)
N(20)
N(23)
C(16)
C(18)
C(17)
C(9)
C(2)
C(3)
C(11)
C(4)
C(10)
C(5)
C(6)
C(7)
C(21)
C(22)
C(24)
C(25)
C(8)
H(231)
H(232)
H(16)
H(181)
H(182)
H(171)
H(172)
H(2)
H(5)
H(211)
H(212)
H(221)
H(222)
H(241)
H(242)
H(251)
H(252)

Invariom Name
F@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O@6c
O1h1h
O1h1h
O1h1h
O1h1h
O1h1h
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]@3c
N@6c1c1c
N1c1c1h1h
3-C#3c[#3c1h1h]#3c[#3c1h1h]@6n1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
66-C#6n[#6c@3c]#66c[#6c#6c]#6c[#6c1h]
6-C#6n[#66c@3c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
C1.5o1.5o@6c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#6c1f]#6c[#66c1h]1n
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
6-C#66c[#6n#66c]#6c[#6c1n]1h
H1n[1c1c1h]
H1n[1c1c1h]
H@3c
H@3c
H@3c
H@3c
H@3c
H@6c
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]

Model Compound
1-fluorobenzene
benzoic acid anion
benzoic acid anion
pyran-4-one (-pyrone)
water
water
water
water
water
water
1-cyclopropylquinolin-4-one
N,N -dimethylbenzenamine
dimethylammonium
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylquinolin-2-one
1-cyclopropyl-3-methylquinolin-4-one
3-methylquinolin-4-one
benzoic acid anion
3-methyl-chromen-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoronaphthalen-2-amine
3-fluoronaphthalen-2-amine
ethylamine
ethylamine
ethylamine
ethylamine
7-aminoquinolin-2-one
dimethylammonium
dimethylammonium
cyclopropane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
benzene
benzene
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine

Electronic Supplementary Material (ESI) for CrystEngComm


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Atom
H(8)
H(21)
H(22)
H(31)
H(32)
H(41)
H(42)
H(51)
H(52)
H(61)
H(62)
H(71)
H(72)

Invariom Name
H@6c
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
benzene
water
water
water
water
water
water
water
water
water
water
water
water

Table 9: Aspherical atomic scattering factors for ciprofloxacin HCl 1.4 H2 O. Invariom names and corresponding model compounds from the invariom database
are listed for all atoms.
Atom
Cl-(1)
F(15)
O(12)
O(13)
O(14)
O(2)
O(31)
N(1)
N(20)
N(23)
C(16)
C(18)
C(17)
C(9)
C(2)
C(3)
C(11)
C(4)
C(10)
C(5)
C(6)
C(7)
C(21)
C(22)
C(24)
C(25)
C(8)
H(13)
H(231)

Invariom Name
Cl
F@6c
O2c
O1c1h
O@6c
O1h1h
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]@3c
N@6c1c1c
N1c1c1h1h
3-C#3c[#3c1h1h]#3c[#3c1h1h]@6n1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
66-C#6n[#6c@3c]#66c[#6c#6c]#6c[#6c1h]
6-C#6n[#66c@3c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
C2o1o@6c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#6c1f]#6c[#66c1h]1n
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
6-C#66c[#6n#66c]#6c[#6c1n]1h
H1o[1c]
H1n[1c1c1h]

Model Compound
chloride
1-fluorobenzene
formaldehyde
methanol
pyran-4-one (-pyrone)
water
water
1-cyclopropylquinolin-4-one
N,N -dimethylbenzenamine
dimethylammonium
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylquinolin-2-one
1-cyclopropyl-3-methylquinolin-4-one
3-methylquinolin-4-one
benzoic acid
3-methyl-chromen-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoronaphthalen-2-amine
3-fluoronaphthalen-2-amine
ethylamine
ethylamine
ethylamine
ethylamine
7-aminoquinolin-2-one
methanol
dimethylammonium

Electronic Supplementary Material (ESI) for CrystEngComm


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Atom
H(232)
H(16)
H(181)
H(182)
H(171)
H(172)
H(2)
H(5)
H(211)
H(212)
H(221)
H(222)
H(241)
H(242)
H(251)
H(252)
H(8)
H(21)
H(22)
H(31)
H(32)

Invariom Name
H1n[1c1c1h]
H@3c
H@3c
H@3c
H@3c
H@3c
H@6c
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H@6c
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
dimethylammonium
cyclopropane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
benzene
benzene
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
benzene
water
water
water
water

Table 10: Aspherical atomic scattering factors for enoxacin 1.72 H2 O. Invariom
names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
F(15)
F(65)
O(12)
O(13)
O(14)
O(62)
O(63)
O(64)
O(1)
O(2)
O(3)
O(4)
O(5)
N(1)
N(8)
N(20)
N(23)
N(51)
N(58)
N(70)
N(73)
C(2)

Invariom Name
F@6c
F@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O@6c
O1h1h
O1h1h
O1h1h
O1h1h
O1h1h
6-N#66c[#6n#66c]#6c[#6c1h]1c
6-N#66c[#6n#66c]#6c[#6c1n]
N@6c1c1c
N1c1c1h1h
6-N#66c[#6n#66c]#6c[#6c1h]1c
6-N#66c[#6n#66c]#6c[#6c1n]
N@6c1c1c
N1c1c1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h

Model Compound
1-fluorobenzene
1-fluorobenzene
benzoic acid anion
benzoic acid anion
pyran-4-one (-pyrone)
benzoic acid anion
benzoic acid anion
pyran-4-one (-pyrone)
water
water
water
water
water
1-methyl-1,8-naphthyridin-4-one
1,8-naphthyridin-2-amine
N,N -dimethylbenzenamine
dimethylammonium
1-methyl-1,8-naphthyridin-4-one
1,8-naphthyridin-2-amine
N,N -dimethylbenzenamine
dimethylammonium
1,3-dimethylquinolin-4-one

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Atom
C(3)
C(4)
C(5)
C(6)
C(7)
C(9)
C(10)
C(11)
C(16)
C(17)
C(21)
C(22)
C(24)
C(25)
C(52)
C(53)
C(54)
C(55)
C(56)
C(57)
C(59)
C(60)
C(61)
C(66)
C(67)
C(71)
C(72)
C(74)
C(75)
H(2)
H(5)
H(161)
H(612)
H(171)
H(172)
H(173)
H(221)
H(222)
H(232)
H(231)
H(241)
H(242)
H(251)
H(252)
H(211)
H(212)
H(52)
H(55)
H(661)
H(662)
H(671)

Invariom Name
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6n1n]#6c[#66c1h]1f
6-C#6n[#66c]#6c[#6c1f]1n
66-C#6n[#6c1c]#6n[#6c]#66c[#6c#6c]
66-C#66c[#6n#6n]#6c[2o#6c]#6c[#6c1h]
C1.5o1.5o@6c
C@6n1c1h1h
C1c1h1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6n1n]#6c[#66c1h]1f
6-C#6n[#66c]#6c[#6c1f]1n
66-C#6n[#6c1c]#6n[#6c]#66c[#6c#6c]
66-C#66c[#6n#6n]#6c[2o#6c]#6c[#6c1h]
C1.5o1.5o@6c
C@6n1c1h1h
C1c1h1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
H@6c
H@6c
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1n[1c1c1h]
H1n[1c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H@6c
H@6c
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1c1h1h]

Model Compound
3-methylquinolin-4-one
3-methyl-chromen-4-one
2-fluoronaphthalen
3-fluoroquinolin-2-amine
3-fluoroquinolin-2-amine
1-methyl-1,8-naphthyridin-4-one
1,8-naphthyridin-4-one
benzoic acid anion
1-ethylpylpyridine-2-one
ethane
ethylamine
ethylamine
ethylamine
ethylamine
1,3-dimethylquinolin-4-one
3-methylquinolin-4-one
3-methyl-chromen-4-one
2-fluoronaphthalen
3-fluoroquinolin-2-amine
3-fluoroquinolin-2-amine
1-methyl-1,8-naphthyridin-4-one
1,8-naphthyridin-4-one
benzoic acid anion
1-ethylpylpyridine-2-one
ethane
ethylamine
ethylamine
ethylamine
ethylamine
benzene
benzene
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethane
ethane
ethane
ethylamine
ethylamine
dimethylammonium
dimethylammonium
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
benzene
benzene
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethane

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Atom
H(672)
H(673)
H(711)
H(712)
H(721)
H(722)
H(731)
H(732)
H(741)
H(742)
H(751)
H(752)
H(11)
H(12)
H(21)
H(22)
H(31)
H(32)
H(41)
H(42)
H(51)
H(53)

Invariom Name
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1n[1c1c1h]
H1n[1c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
ethane
ethane
ethylamine
ethylamine
ethylamine
ethylamine
dimethylammonium
dimethylammonium
ethylamine
ethylamine
ethylamine
ethylamine
water
water
water
water
water
water
water
water
water
water

Table 11: Aspherical atomic scattering factors for enoxacin 3 H2 O. Invariom


names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
F(15)
O(14)
O(12)
O(13)
O(4)
O(5)
O(6)
N(1)
N(8)
N(20)
N(23)
C(2)
C(3)
C(4)
C(10)
C(5)
C(6)
C(7)
C(9)
C(16)
C(17)

Invariom Name
F@6c
O@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O1h1h
O1h1h
O1h1h
6-N#66c[#6n#66c]#6c[#6c1h]1c
6-N#66c[#6n#66c]#6c[#6c1n]
N@6c1c1c
N1c1c1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6n]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6n1n]#6c[#66c1h]1f
6-C#6n[#66c]#6c[#6c1f]1n
66-C#6n[#6c1c]#6n[#6c]#66c[#6c#6c]
C@6n1c1h1h
C1c1h1h1h

Model Compound
1-fluorobenzene
pyran-4-one (-pyrone)
benzoic acid anion
benzoic acid anion
water
water
water
1-methyl-1,8-naphthyridin-4-one
1,8-naphthyridin-2-amine
N,N -dimethylbenzenamine
dimethylammonium
1,3-dimethylquinolin-4-one
3-methylquinolin-4-one
3-methyl-chromen-4-one
1,8-naphthyridin-4-one
2-fluoronaphthalen
3-fluoroquinolin-2-amine
3-fluoroquinolin-2-amine
1-methyl-1,8-naphthyridin-4-one
1-ethylpylpyridine-2-one
ethane

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Atom
C(11)
C(25)
C(24)
C(22)
C(21)
H(23A)
H(23B)
H(2)
H(5)
H(16A)
H(16B)
H(17A)
H(17B)
H(17C)
H(25A)
H(25B)
H(24A)
H(24B)
H(22A)
H(22B)
H(21A)
H(21B)
H(041)
H(042)
H(051)
H(052)
H(061)
H(062)

Invariom Name
C1.5o1.5o@6c
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
H1n[1c1c1h]
H1n[1c1c1h]
H@6c
H@6c
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
benzoic acid anion
ethylamine
ethylamine
ethylamine
ethylamine
dimethylammonium
dimethylammonium
benzene
benzene
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethane
ethane
ethane
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
water
water
water
water
water
water

Table 12: Aspherical atomic scattering factors for fleroxacin H2 O HCl. Invariom
names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
Cl-(1)
F(15)
F(8)
F(17)
O(13)
O(12)
O(14)
O(2)
N(1)
N(20)
N(23)
C(11)
C(3)
C(4)
C(10)
C(9)

Invariom Name
Cl
F@6c
F@6c
F1c
O1c1h
O2c
O@6c
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
N1c1c1c1h
C2o1o@6c
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1f]

Model Compound
chloride
1-fluorobenzene
1-fluorobenzene
fluoromethane
methanol
formaldehyde
pyran-4-one (-pyrone)
water
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
trimethylammonium
benzoic acid
3-methylquinolin-4-one
3-methyl-chromen-4-one
quinolin-4-one
8-fluoro-1-methylquinolin-2-one

Electronic Supplementary Material (ESI) for CrystEngComm


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Atom
C(2)
C(16)
C(17)
C(8)
C(7)
C(6)
C(5)
C(25)
C(24)
C(19)
C(21)
C(26)
H(13)
H(23)
H(2)
H(161)
H(162)
H(171)
H(172)
H(5)
H(251)
H(252)
H(241)
H(242)
H(191)
H(192)
H(211)
H(212)
H(261)
H(262)
H(263)
H(21)
H(22)

Invariom Name
6-C#6n[#66c1c]#6c[#6c1c]1h
C@6n1c1h1h
C1f1c1h1h
6-C#66c[#6n#66c]#6c[#6c1n]1f
6-C#6c[#66c1f]#6c[#6c1f]1n
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#66c[#66c#6c]#6c[#6c1f]1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1h1h1h
H1o[1c]
H1n[1c1c1c]
H@6c
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1f1c1h]
H1c[1f1c1h]
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1h1h]
H1c[1n1h1h]
H1c[1n1h1h]
H1o[1h]
H1o[1h]

Model Compound
1,3-dimethylquinolin-4-one
1-ethylpylpyridine-2-one
fluoroethane
7-amino-8-fluoroquinolin-2-one
1,3-difluoronaphthalen-2-amine
3-fluoronaphthalen-2-amine
2-fluoronaphthalen
ethylamine
ethylamine
ethylamine
ethylamine
methylamine
methanol
trimethylammonium
benzene
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
fluoroethane
fluoroethane
benzene
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
methylamine
methylamine
methylamine
water
water

Table 13: Aspherical atomic scattering factors for lomefloxacin 4 H2 O HCl. Invariom names and corresponding model compounds from the invariom database
are listed for all atoms.
Atom
Cl-(1)
F(17)
F(18)
O(1)
O(2)
O(12)
O(13)
O(14)
N(1)
N(20)
N(23A)

Invariom Name
Cl
F@6c
F@6c
O1h1h
O1h1h
O2c
O1c1h
O@6c
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
N1c1c1h1h

Model Compound
chloride
1-fluorobenzene
1-fluorobenzene
water
water
formaldehyde
methanol
pyran-4-one (-pyrone)
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
dimethylammonium

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Atom
N(23B)
C(2)
C(3)
C(5)
C(4)
C(6)
C(7)
C(9)
C(8)
C(10)
C(11)
C(15)
C(16)
C(21A)
C(22A)
C(24A)
C(25A)
C(26A)
C(21B)
C(22B)
C(24B)
C(25B)
C(26B)
H(1A)
H(1B)
H(2A)
H(2B)
H(2)
H(5)
H(13)
H(15A)
H(15B)
H(16A)
H(16B)
H(16C)
H(23A)
H(23B)
H(21A)
H(21B)
H(22A)
H(24C)
H(24D)
H(25A)
H(25C)
H(26A)
H(26B)
H(26C)
H(23C)
H(23D)
H(21C)
H(21D)

Invariom Name
N1c1c1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C2o#66c[#66c#6c]#6c[#6c1c]
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#66c1f]#6c[#6c1f]1n
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1f]
6-C#66c[#6n#66c]#6c[#6c1n]1f
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
C2o1o@6c
C@6n1c1h1h
C1c1h1h1h
C1n1c1h1h
C1n1c1c1h
C1n1c1h1h
C1n1c1h1h
C1c1h1h1h
C1n1c1h1h
C1n1c1c1h
C1n1c1h1h
C1n1c1h1h
C1c1h1h1h
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H@6c
H@6c
H1o[1c]
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1n[1c1c1h]
H1n[1c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1n[1c1c1h]
H1n[1c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]

Model Compound
dimethylammonium
1,3-dimethylquinolin-4-one
3-methylquinolin-4-one
2-fluoronaphthalen
3-methyl-chromen-4-one
3-fluoronaphthalen-2-amine
1,3-difluoronaphthalen-2-amine
8-fluoro-1-methylquinolin-2-one
7-amino-8-fluoroquinolin-2-one
quinolin-4-one
benzoic acid
1-ethylpylpyridine-2-one
ethane
ethylamine
2-aminopropane
ethylamine
ethylamine
ethane
ethylamine
2-aminopropane
ethylamine
ethylamine
ethane
water
water
water
water
benzene
benzene
methanol
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethane
ethane
ethane
dimethylammonium
dimethylammonium
ethylamine
ethylamine
2-aminopropane
ethylamine
ethylamine
ethylamine
ethylamine
ethane
ethane
ethane
dimethylammonium
dimethylammonium
ethylamine
ethylamine

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Atom
H(22B)
H(24E)
H(24F)
H(25D)
H(25E)
H(26D)
H(26E)
H(26F)

Invariom Name
H1c[1n1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]

Model Compound
2-aminopropane
ethylamine
ethylamine
ethylamine
ethylamine
ethane
ethane
ethane

Table 14: Aspherical atomic scattering factors for moxifloxacin HCl 0.5 H2 O
0.5 CH3 OH. Invariom names and corresponding model compounds from the
invariom database are listed for all atoms.
Atom
Cl-(1)
Cl-(2)
F(15)
F(65)
O(12)
O(13)
O(14)
O(19)
O(63)
O(62)
O(64)
O(69)
O(4)
O(42)
N(1)
N(20)
N(23)
N(51)
N(70)
N(73)
C(2)
C(3)
C(4)
C(10)
C(5)
C(6)
C(7)
C(8)
C(9)
C(11)
C(16)
C(17)
C(18)
C(19)

Invariom Name
Cl
Cl
F@6c
F@6c
O1c1h
O2c
O@6c
O@6c1c
O1c1h
O2c
O@6c
O@6c1c
O1c1h
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]@3c
N@6c1c1c
N1c1c1h1h
6-N#66c[#66c#6c]#6c[#6c1h]@3c
N@6c1c1c
N1c1c1h1h
6-C#6n[#66c@3c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#6c1f]#6c[#66c1o]1n
6-C#66c[#6n#66c]#6c[#6c1n]1o
66-C#6n[#6c@3c]#66c[#6c#6c]#6c[#6c1o]
C2o1o@6c
3-C#3c[#3c1h1h]#3c[#3c1h1h]@6n1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
C1o1h1h1h

Model Compound
chloride
chloride
1-fluorobenzene
1-fluorobenzene
methanol
formaldehyde
pyran-4-one (-pyrone)
anisole
methanol
formaldehyde
pyran-4-one (-pyrone)
anisole
methanol
water
1-cyclopropylquinolin-4-one
N,N -dimethylbenzenamine
dimethylammonium
1-cyclopropylquinolin-4-one
N,N -dimethylbenzenamine
dimethylammonium
1-cyclopropyl-3-methylquinolin-4-one
3-methylquinolin-4-one
3-methyl-chromen-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoronaphthalen-2-amine
2-amino-3-fluoronaphthalen-1-ol
7-amino-8-hydroxyquinolin-2-one
1-cyclopropyl-8-hydroxy-1,8a-dihydroquinolin-2(3H)-one
benzoic acid
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
methanol

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Atom
C(21)
C(22)
C(24)
C(25)
C(26)
C(27)
C(28)
C(52)
C(53)
C(54)
C(60)
C(55)
C(56)
C(57)
C(58)
C(59)
C(61)
C(66)
C(67)
C(68)
C(69)
C(71)
C(72)
C(74)
C(75)
C(76)
C(77)
C(78)
C(41)
H(12)
H(23A)
H(23B)
H(2)
H(5)
H(16)
H(17A)
H(17B)
H(18A)
H(18B)
H(19A)
H(19B)
H(19C)
H(21A)
H(21B)
H(22A)
H(24A)
H(24B)
H(25A)
H(25B)
H(26A)
H(26B)

Invariom Name
C1n1c1h1h
C1n1c1c1h
C1n1c1h1h
C1c1c1h1h
C1c1c1h1h
C1c1c1c1h
C1n1c1h1h
6-C#6n[#66c@3c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#6c1f]#6c[#66c1o]1n
6-C#66c[#6n#66c]#6c[#6c1n]1o
66-C#6n[#6c@3c]#66c[#6c#6c]#6c[#6c1o]
C2o1o@6c
3-C#3c[#3c1h1h]#3c[#3c1h1h]@6n1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
C1o1h1h1h
C1n1c1h1h
C1n1c1c1h
C1n1c1h1h
C1c1c1h1h
C1c1c1h1h
C1c1c1c1h
C1n1c1h1h
C1o1h1h1h
H1o[1c]
H1n[1c1c1h]
H1n[1c1c1h]
H@6c
H@6c
H@3c
H@3c
H@3c
H@3c
H@3c
H1c[1o1h1h]
H1c[1o1h1h]
H1c[1o1h1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1c1h]

Model Compound
ethylamine
2-aminopropane
ethylamine
propane
propane
isobutane
ethylamine
1-cyclopropyl-3-methylquinolin-4-one
3-methylquinolin-4-one
3-methyl-chromen-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoronaphthalen-2-amine
2-amino-3-fluoronaphthalen-1-ol
7-amino-8-hydroxyquinolin-2-one
1-cyclopropyl-8-hydroxy-1,8a-dihydroquinolin-2(3H)-one
benzoic acid
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
methanol
ethylamine
2-aminopropane
ethylamine
propane
propane
isobutane
ethylamine
methanol
methanol
dimethylammonium
dimethylammonium
benzene
benzene
cyclopropane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
methanol
methanol
methanol
ethylamine
ethylamine
2-aminopropane
ethylamine
ethylamine
propane
propane
propane
propane

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Atom
H(27)
H(28A)
H(28B)
H(63)
H(73A)
H(73B)
H(52)
H(55)
H(66)
H(67A)
H(67B)
H(68A)
H(68B)
H(69A)
H(69B)
H(69C)
H(71A)
H(71B)
H(72)
H(74A)
H(74B)
H(75A)
H(75B)
H(76A)
H(76B)
H(77)
H(78A)
H(78B)
H(04)
H(41A)
H(41B)
H(41C)
H(42A)
H(42B)

Invariom Name
H1c[1c1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1o[1c]
H1n[1c1c1h]
H1n[1c1c1h]
H@6c
H@6c
H@3c
H@3c
H@3c
H@3c
H@3c
H1c[1o1h1h]
H1c[1o1h1h]
H1c[1o1h1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1o[1c]
H1c[1o1h1h]
H1c[1o1h1h]
H1c[1o1h1h]
H1o[1h]
H1o[1h]

Model Compound
isobutane
ethylamine
ethylamine
methanol
dimethylammonium
dimethylammonium
benzene
benzene
cyclopropane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
methanol
methanol
methanol
ethylamine
ethylamine
2-aminopropane
ethylamine
ethylamine
propane
propane
propane
propane
isobutane
ethylamine
ethylamine
methanol
methanol
methanol
methanol
water
water

Table 15: Aspherical atomic scattering factors for nadifloxacin 0.5 H2 O. Invariom names and corresponding model compounds from the invariom database
are listed for all atoms.
Atom
F(15)
F(65)
O(14)
O(13)
O(12)
O(23)
O(63)
O(62)
O(73)
O(64)

Invariom Name
F@6c
F@6c
O@6c
O2c
O1c1h
O1c1h
O2c
O1c1h
O1c1h
O@6c

Model Compound
1-fluorobenzene
1-fluorobenzene
pyran-4-one (-pyrone)
formaldehyde
methanol
methanol
formaldehyde
methanol
methanol
pyran-4-one (-pyrone)

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Atom
O(4)
N(1)
N(20)
N(70)
N(51)
C(9)
C(8)
C(3)
C(10)
C(5)
C(7)
C(4)
C(6)
C(11)
C(16)
C(21)
C(25)
C(22)
C(19)
C(2)
C(17)
C(18)
C(24)
C(23)
C(59)
C(54)
C(57)
C(55)
C(53)
C(56)
C(58)
C(60)
C(68)
C(66)
C(67)
C(52)
C(71)
C(61)
C(74)
C(75)
C(72)
C(69)
C(73)
H(12)
H(23)
H(5)
H(161)
H(162)
H(211)
H(212)
H(251)

Invariom Name
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
N@6c1c1c
6-N#66c[#66c#6c]#6c[#6c1h]1c
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1c]
6-C#66c[#6n#66c]#6c[#6c1n]1c
6-C#6c[2o#66c]#6c[#6n1h]1c
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1f]#6c[#66c1c]1n
6-C2o#66c[#66c#6c]#6c[#6c1c]
6-C#6c[#6c1n]#6c[#66c1h]1f
C2o1o@6c
C@6c1c1h1h
C1n1c1h1h
C1n1c1h1h
C1c1c1h1h
C1c1h1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h
C1c1c1h1h
C@6n1c1c1h
C1c1c1h1h
C1o1c1c1h
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1c]
6-C2o#66c[#66c#6c]#6c[#6c1c]
6-C#6c[#6c1f]#6c[#66c1c]1n
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#66c[#6n#66c]#6c[#6c1n]1c
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
C@6n1c1c1h
C@6c1c1h1h
C1c1c1h1h
6-C#6n[#66c1c]#6c[#6c1c]1h
C1n1c1h1h
C2o1o@6c
C1c1c1h1h
C1n1c1h1h
C1c1c1h1h
C1c1h1h1h
C1o1c1c1h
H1o[1c]
H1o[1c]
H@6c
H1c[@6c1c1h]
H1c[@6c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]

Model Compound
water
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
N,N -dimethylbenzenamine
1,3-dimethylquinolin-4-one
2,3-dihydro-5-oxo-(1H,5H)-benzo[ij]quinolizine
8-methylquinolin-7-amine
3-methylquinolin-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoro-1-methylnaphthalen-2-amine
3-methyl-chromen-4-one
3-fluoronaphthalen-2-amine
benzoic acid
isochroman
ethylamine
ethylamine
propane
ethane
1,3-dimethylquinolin-4-one
propane
1-isopropylpyridin-2-one
propane
2-propanol
2,3-dihydro-5-oxo-(1H,5H)-benzo[ij]quinolizine
3-methyl-chromen-4-one
3-fluoro-1-methylnaphthalen-2-amine
2-fluoronaphthalen
3-methylquinolin-4-one
3-fluoronaphthalen-2-amine
8-methylquinolin-7-amine
quinolin-4-one
1-isopropylpyridin-2-one
isochroman
propane
1,3-dimethylquinolin-4-one
ethylamine
benzoic acid
propane
ethylamine
propane
ethane
2-propanol
methanol
methanol
benzene
isochroman
isochroman
ethylamine
ethylamine
ethylamine

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Atom
H(252)
H(221)
H(222)
H(191)
H(192)
H(193)
H(2)
H(171)
H(172)
H(18)
H(241)
H(242)
H(231)
H(62)
H(73)
H(55)
H(68)
H(661)
H(662)
H(671)
H(672)
H(52)
H(711)
H(712)
H(741)
H(742)
H(751)
H(752)
H(721)
H(722)
H(691)
H(692)
H(693)
H(731)
H(41)
H(42)

Invariom Name
H1c[1n1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H@6c
H1c[1c1c1h]
H1c[1c1c1h]
H1c[@6n1c1c]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1o1c1c]
H1o[1c]
H1o[1c]
H@6c
H1c[@6n1c1c]
H1c[@6c1c1h]
H1c[@6c1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1c1h]
H1c[1c1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1o1c1c]
H1o[1h]
H1o[1h]

Model Compound
ethylamine
propane
propane
ethane
ethane
ethane
benzene
propane
propane
1-isopropylpyridin-2-one
propane
propane
2-propanol
methanol
methanol
benzene
1-isopropylpyridin-2-one
isochroman
isochroman
propane
propane
benzene
ethylamine
ethylamine
propane
propane
ethylamine
ethylamine
propane
propane
ethane
ethane
ethane
2-propanol
water
water

Table 16: Aspherical atomic scattering factors for norfloxacin anhydrate. Invariom names and corresponding model compounds from the invariom database
are listed for all atoms.
Atom
F(15)
O(12)
O(13)
O(14)
N(1)
N(20)
N(23)
C(2)
C(3)

Invariom Name
F@6c
O2c
O1c1h
O@6c
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
N1c1c1h
6-C#6n[#66c1c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c

Model Compound
1-fluorobenzene
formaldehyde
methanol
pyran-4-one (-pyrone)
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
dimethylamine
1,3-dimethylquinolin-4-one
3-methylquinolin-4-one

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Atom
C(11)
C(4)
C(10)
C(5)
C(6)
C(7)
C(8)
C(9)
C(25)
C(24)
C(22)
C(21)
C(16)
C(17)
H(13)
H(23A)
H(2)
H(5)
H(8)
H(25A)
H(25B)
H(24A)
H(24B)
H(22A)
H(22B)
H(21A)
H(21B)
H(16A)
H(16B)
H(17A)
H(17B)
H(17C)

Invariom Name
C2o1o@6c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#6c[#6c1f]#6c[#66c1h]1n
6-C#66c[#6n#66c]#6c[#6c1n]1h
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1h]
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C@6n1c1h1h
C1c1h1h1h
H1o[1c]
H1n[1c1c]
H@6c
H@6c
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]

Model Compound
benzoic acid
3-methyl-chromen-4-one
quinolin-4-one
2-fluoronaphthalen
3-fluoronaphthalen-2-amine
3-fluoronaphthalen-2-amine
7-aminoquinolin-2-one
1,3-dimethylquinolin-4-one
ethylamine
ethylamine
ethylamine
ethylamine
1-ethylpylpyridine-2-one
ethane
methanol
dimethylamine
benzene
benzene
benzene
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethane
ethane
ethane

Table 17: Aspherical atomic scattering factors for norfloxacin 2 H2 O. Invariom


names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
F(15)
O(13)
O(12)
O(14)
O(2)
O(3)
N(23)
N(1)
N(20)
C(6)
C(11)
C(4)

Invariom Name
F@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O@6c
O1h1h
O1h1h
N1c1c1h1h
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
6-C#6c[#6c1n]#6c[#66c1h]1f
C1.5o1.5o@6c
6-C2o#66c[#66c#6c]#6c[#6c1c]

Model Compound
1-fluorobenzene
benzoic acid anion
benzoic acid anion
pyran-4-one (-pyrone)
water
water
dimethylammonium
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
3-fluoronaphthalen-2-amine
benzoic acid anion
3-methyl-chromen-4-one

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Atom
C(3)
C(10)
C(5)
C(2)
C(9)
C(8)
C(7)
C(16)
C(25)
C(21)
C(24)
C(22)
C(17)
H(23A)
H(23B)
H(5)
H(2)
H(8)
H(16A)
H(16B)
H(25A)
H(25B)
H(21A)
H(21B)
H(24A)
H(24B)
H(22A)
H(22B)
H(17A)
H(17B)
H(17C)
H(021)
H(022)
H(031)
H(032)

Invariom Name
6-C#6c[2o#66c]#6c[#6n1h]1c
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6n[#66c1c]#6c[#6c1c]1h
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1h]
6-C#66c[#6n#66c]#6c[#6c1n]1h
6-C#6c[#6c1f]#6c[#66c1h]1n
C@6n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C1c1h1h1h
H1n[1c1c1h]
H1n[1c1c1h]
H@6c
H@6c
H@6c
H1c[@6n1c1h]
H1c[@6n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
3-methylquinolin-4-one
quinolin-4-one
2-fluoronaphthalen
1,3-dimethylquinolin-4-one
1,3-dimethylquinolin-4-one
7-aminoquinolin-2-one
3-fluoronaphthalen-2-amine
1-ethylpylpyridine-2-one
ethylamine
ethylamine
ethylamine
ethylamine
ethane
dimethylammonium
dimethylammonium
benzene
benzene
benzene
1-ethylpylpyridine-2-one
1-ethylpylpyridine-2-one
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethane
ethane
ethane
water
water
water
water

Table 18: Aspherical atomic scattering factors for ofloxacin. Invariom names
and corresponding model compounds from the invariom database are listed for
all atoms.
Atom
F(15)
O(13)
O(14)
O(12)
O(16)
N(1)
N(20)
N(23)
C(2)
C(9)

Invariom Name
F@6c
O2c
O@6c
O1c1h
O@6c1c
6-N#66c[#66c#6c]#6c[#6c1h]1c
N@6c1c1c
N1c1c1c
6-C#6n[#66c1c]#6c[#6c1c]1h
66-C#6n[#6c1c]#66c[#6c#6c]#6c[#6c1o]

Model Compound
1-fluorobenzene
formaldehyde
pyran-4-one (-pyrone)
methanol
anisole
1,3-dimethylquinolin-4-one
N,N -dimethylbenzenamine
trimethylamine
1,3-dimethylquinolin-4-one
8-hydroxy-1-methylquinolin-2-one

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Atom
C(10)
C(11)
C(3)
C(6)
C(5)
C(7)
C(8)
C(4)
C(24)
C(21)
C(22)
C(18)
C(17)
C(19)
C(26)
C(25)
H(2)
H(12)
H(5)
H(24A)
H(24B)
H(21A)
H(21B)
H(22A)
H(22B)
H(18)
H(17A)
H(17B)
H(19A)
H(19B)
H(19C)
H(26A)
H(26B)
H(26C)
H(25A)
H(25B)

Invariom Name
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1h]
C2o1o@6c
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C#6c[#6c1n]#6c[#66c1h]1f
6-C#66c[#66c#6c]#6c[#6c1f]1h
6-C#6c[#6c1f]#6c[#66c1o]1n
6-C#66c[#6n#66c]#6c[#6c1n]1o
6-C2o#66c[#66c#6c]#6c[#6c1c]
C1n1c1h1h
C1n1c1h1h
C1n1c1h1h
C@6n1c1c1h
C1o1c1h1h
C1c1h1h1h
C1n1h1h1h
C1n1c1h1h
H@6c
H1o[1c]
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[@6n1c1c]
H1c[1o1c1h]
H1c[1o1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1n1h1h]
H1c[1n1h1h]
H1c[1n1h1h]
H1c[1n1c1h]
H1c[1n1c1h]

Model Compound
quinolin-4-one
benzoic acid
3-methylquinolin-4-one
3-fluoronaphthalen-2-amine
2-fluoronaphthalen
2-amino-3-fluoronaphthalen-1-ol
7-amino-8-hydroxyquinolin-2-one
3-methyl-chromen-4-one
ethylamine
ethylamine
ethylamine
1-isopropylpyridin-2-one
ethanol
ethane
methylamine
ethylamine
benzene
methanol
benzene
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
ethylamine
1-isopropylpyridin-2-one
ethanol
ethanol
ethane
ethane
ethane
methylamine
methylamine
methylamine
ethylamine
ethylamine

Table 19: Aspherical atomic scattering factors for sparfloxacin 3 H2 O. Invariom


names and corresponding model compounds from the invariom database are
listed for all atoms.
Atom
F(8)
F(15)
O(12)
O(13)
O(14)
O(2)
O(3)
O(4)
N(1)
N(5)
N(20)

Invariom Name
F@6c
F@6c
O1.5c[1.5o@6c]
O1.5c[1.5o@6c]
O@6c
O1h1h
O1h1h
O1h1h
6-N#66c[#66c#6c]#6c[#6c1h]@3c
=-N@6c1h1h
N@6c1c1c

Model Compound
1-fluorobenzene
1-fluorobenzene
benzoic acid anion
benzoic acid anion
pyran-4-one (-pyrone)
water
water
water
1-cyclopropylquinolin-4-one
4-aminopyrimidin-2-one
N,N -dimethylbenzenamine

Electronic Supplementary Material (ESI) for CrystEngComm


This journal is The Royal Society of Chemistry 2011

Atom
N(23)
C(2)
C(3)
C(4)
C(10)
C(9)
C(8)
C(7)
C(6)
C(5)
C(21)
C(22)
C(24)
C(25)
C(27)
C(26)
C(16)
C(17)
C(18)
C(11)
H(52)
H(51)
H(23A)
H(23B)
H(2)
H(21A)
H(21B)
H(22A)
H(24A)
H(251)
H(252)
H(27A)
H(27B)
H(27C)
H(26A)
H(26B)
H(26C)
H(16)
H(17A)
H(17B)
H(18A)
H(18B)
H(021)
H(022)
H(031)
H(032)
H(041)
H(042)

Invariom Name
N1c1c1h1h
6-C#6n[#66c@3c]#6c[#6c1c]1h
6-C#6c[2o#66c]#6c[#6n1h]1c
6-C2o#66c[#66c#6c]#6c[#6c1c]
66-C#66c[#6n#6c]#6c[2o#6c]#6c[#6c1n]
66-C#6n[#6c@3c]#66c[#6c#6c]#6c[#6c1f]
6-C#66c[#6n#66c]#6c[#6c1n]1f
6-C#6c[#66c1f]#6c[#6c1f]1n
6-C#6c[#66c1n]#6c[#6c1n]1f
6-C#66c[#66c#6c]#6c[#6c1f]1n
C1n1c1h1h
C1n1c1c1h
C1n1c1c1h
C1n1c1h1h
C1c1h1h1h
C1c1h1h1h
3-C#3c[#3c1h1h]#3c[#3c1h1h]@6n1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
3-C#3c[#3c@6n1h]#3c[#3c1h1h]1h1h
C1.5o1.5o@6c
H1n[@6c1h]
H1n[@6c1h]
H1n[1c1c1h]
H1n[1c1c1h]
H@6c
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1n1c1c]
H1c[1n1c1c]
H1c[1n1c1h]
H1c[1n1c1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H1c[1c1h1h]
H@3c
H@3c
H@3c
H@3c
H@3c
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]
H1o[1h]

Model Compound
dimethylammonium
1-cyclopropyl-3-methylquinolin-4-one
3-methylquinolin-4-one
3-methyl-chromen-4-one
5-aminoquinolin-4-one
1-cyclopropyl-8-fluoroquinolin-2-one
7-amino-8-fluoroquinolin-2-one
1,3-difluoronaphthalen-2-amine
2-fluoronaphthalene-1,3-diamine
2-fluoronaphthalen-1-amine
ethylamine
2-aminopropane
2-aminopropane
ethylamine
ethane
ethane
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
1-cyclopropylpyridine-2-one
benzoic acid anion
aniline
aniline
dimethylammonium
dimethylammonium
benzene
ethylamine
ethylamine
2-aminopropane
2-aminopropane
ethylamine
ethylamine
ethane
ethane
ethane
ethane
ethane
ethane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
cyclopropane
water
water
water
water
water
water