The experimental electron density in polymorphs A and B of the anti-ulcer drug famotidine

Overgaard, J.; Hibbs, D.E.

doi:10.1107/S0108767304017891

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The experimental electron density in polymorphs A and B of the anti-ulcer drug famotidine

J. Overgaard and D. E. Hibbs

Accurate structure factors have been measured for the two known conformational polymorphs (A and B) of famotidine up to a maximum resolution of sin(θ)

λ = 1.2 Å⁻¹ at 100 K using a conventional X-ray source and a CCD-based diffractometer. The experimental electron-density distribution was modelled using a multipole model and the interatomic interactions were analysed following the atoms-in-molecules theory. Excellent equivalence between most electronic and electrostatic properties in the polymorphs exists and no significant differences were found to exist across polymorphs either in the interatomic interactions (via the topological analysis) or in the atomic charges from integration of the atomic basins. Additional derived properties, such as the molecular dipole moment, similarly did not distinguish between the polymorphs. Only the molecular electrostatic potential mapped on top of the molecular surface, i.e. the isodensity contoured at 0.00675 e Å⁻³, was able to uncover the differences between A and B. In both conformations, the sizes of the electronegative and electropositive areas match. However, the average electrostatic potential in the electronegative area of A is −40 kJ mol⁻¹, while the corresponding value in B is −55 kJ mol⁻¹. Together with the physical shape and dimensions of A and B, this leads to a conclusion that the polymorphs are mutually exclusive at the same receptor binding site.

Keywords: electron density; charge density; famotidine.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767304017891/xc5012sup1.cif Contains datablocks global, fama, famb
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108767304017891/xc5012sup2.pdf Residual and static model densities
	Structure factor file (CIF format) https://doi.org/10.1107/S0108767304017891/xc5012famasup3.fcf Contains datablock fama0m
	Structure factor file (CIF format) https://doi.org/10.1107/S0108767304017891/xc5012fambsup4.fcf Contains datablock fambm

CCDC references: 215086; 215087

Computing details top

Figures top

(fama) top

Crystal data top

C₈H₁₅N₇O₂S₃	F(000) = 504
M_r = 337.45	D_x = 1.595 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 16250 reflections
a = 11.9115 (3) Å	θ = 2.3–59.3°
b = 7.1876 (2) Å	µ = 0.54 mm⁻¹
c = 16.6236 (4) Å	T = 100 K
β = 100.045 (1)°	Block, white
V = 1401.4 (1) Å³	0.35 × 0.35 × 0.30 mm
Z = 4

Data collection top

Bruker CCD area detector diffractometer	20197 independent reflections
Radiation source: fine-focus sealed tube	16610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω–scans and π–scans	θ_max = 59.5°, θ_min = 1.8°
Absorption correction: analytical ?	h = −28→28
T_min = 0.787, T_max = 0.887	k = 0→17
68907 measured reflections	l = 0→39

Refinement top

Refinement on F	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	Riding
wR(F²) = 0.021	w = 1/[σ²(F_o²)]
S = 1.70	(Δ/σ)_max < 0.001
16610 reflections	Δρ_max = 0.29 e Å⁻³
459 parameters	Δρ_min = −0.28 e Å⁻³
1 restraint	Extinction correction: SHELXL, none
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

Crystal data top

C₈H₁₅N₇O₂S₃	V = 1401.4 (1) Å³
M_r = 337.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.9115 (3) Å	µ = 0.54 mm⁻¹
b = 7.1876 (2) Å	T = 100 K
c = 16.6236 (4) Å	0.35 × 0.35 × 0.30 mm
β = 100.045 (1)°

Data collection top

Bruker CCD area detector diffractometer	20197 independent reflections
Absorption correction: analytical ?	16610 reflections with I > 2σ(I)
T_min = 0.787, T_max = 0.887	R_int = 0.020
68907 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	1 restraint
wR(F²) = 0.021	Riding
S = 1.70	Δρ_max = 0.29 e Å⁻³
16610 reflections	Δρ_min = −0.28 e Å⁻³
459 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S(1)	0.315075 (6)	0.561307 (10)	0.678851 (5)	0.016
S(11)	0.189700 (7)	−0.058633 (9)	0.780479 (5)	0.016
S(17)	0.165730 (5)	0.480806 (8)	0.985180 (4)	0.011
O(19)	0.28332 (3)	0.43673 (5)	0.98160 (2)	0.017
O(20)	0.12947 (4)	0.66963 (4)	0.96721 (2)	0.019
N(3)	0.37674 (2)	0.21698 (4)	0.69832 (2)	0.014
N(6)	0.44159 (2)	0.38131 (3)	0.58723 (2)	0.015
N(8)	0.52513 (3)	0.08170 (4)	0.60768 (2)	0.018
N(9)	0.56204 (4)	0.27215 (4)	0.50447 (2)	0.022
N(15)	0.15104 (3)	0.06788 (3)	0.97858 (2)	0.018
N(16)	0.07858 (2)	0.35592 (3)	0.92209 (1)	0.012
N(18)	0.14725 (2)	0.41919 (4)	1.07640 (2)	0.015
C(2)	0.38629 (2)	0.36292 (4)	0.65144 (2)	0.013
C(4)	0.31408 (2)	0.25961 (4)	0.75872 (2)	0.014
C(5)	0.27197 (2)	0.43651 (4)	0.75710 (2)	0.016
C(7)	0.50809 (2)	0.24405 (4)	0.56790 (2)	0.015
C(10)	0.29956 (3)	0.11283 (5)	0.81953 (2)	0.016
C(12)	0.06027 (3)	0.07637 (4)	0.77651 (2)	0.015
C(13)	0.00932 (2)	0.07211 (4)	0.85552 (2)	0.015
C(14)	0.08440 (2)	0.17164 (3)	0.92439 (1)	0.012
H(8A)	0.57889	−0.01338	0.59084	0.033
H(8B)	0.48641	0.05630	0.65592	0.031
H(9A)	0.55655	0.39593	0.47541	0.032
H(9B)	0.61486	0.17154	0.49100	0.034
H(15A)	0.20850	0.12474	1.02366	0.039
H(15B)	0.14509	−0.07133	0.97123	0.029
H(18A)	0.21759	0.44294	1.11859	0.033
H(18B)	0.07619	0.47129	1.09327	0.031
H(5)	0.21944	0.49052	0.79875	0.023
H(10A)	0.27715	0.17891	0.87393	0.027
H(10B)	0.38101	0.04093	0.83808	0.024
H(12A)	0.07857	0.22104	0.76268	0.021
H(12B)	−0.00371	0.02440	0.72613	0.022
H(13A)	−0.07490	0.13781	0.84417	0.024
H(13B)	−0.00175	−0.07259	0.87321	0.022

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S(1)	0.01534 (2)	0.01255 (2)	0.01842 (3)	0.00217 (2)	0.00433 (2)	−0.00062 (2)
S(11)	0.02180 (3)	0.01146 (2)	0.01574 (3)	0.00180 (2)	0.00622 (2)	−0.00028 (2)
S(17)	0.01237 (2)	0.00824 (2)	0.01259 (2)	−0.00089 (1)	0.00240 (1)	−0.00048 (1)
O(19)	0.01226 (9)	0.01737 (10)	0.02166 (12)	−0.00249 (8)	0.00450 (8)	−0.00304 (9)
O(20)	0.0255 (1)	0.0081 (1)	0.0217 (1)	0.0003 (1)	0.0036 (1)	0.0010 (1)
N(3)	0.01436 (7)	0.01354 (7)	0.01522 (8)	0.00179 (6)	0.00414 (6)	0.00106 (6)
N(6)	0.01615 (8)	0.01193 (6)	0.01693 (8)	0.00192 (6)	0.00599 (6)	0.00060 (6)
N(8)	0.0185 (1)	0.0155 (1)	0.0204 (1)	0.0060 (1)	0.0057 (1)	0.0040 (1)
N(9)	0.0268 (1)	0.0159 (1)	0.0246 (1)	0.0068 (1)	0.0144 (1)	0.0036 (1)
N(15)	0.0284 (1)	0.0092 (1)	0.0154 (1)	0.0009 (1)	−0.0020 (1)	0.0003 (1)
N(16)	0.01315 (6)	0.00943 (6)	0.01218 (6)	−0.00028 (5)	0.00137 (5)	−0.00017 (5)
N(18)	0.01661 (9)	0.01667 (8)	0.01149 (8)	0.00036 (7)	0.00127 (6)	−0.00075 (6)
C(2)	0.01206 (7)	0.01225 (7)	0.01466 (8)	0.00076 (6)	0.00268 (6)	−0.00024 (6)
C(4)	0.01240 (7)	0.01525 (8)	0.01364 (8)	0.00102 (6)	0.00222 (6)	−0.00010 (6)
C(5)	0.01496 (8)	0.01612 (8)	0.01654 (9)	0.00217 (7)	0.00411 (7)	−0.00158 (7)
C(7)	0.01450 (8)	0.01263 (7)	0.01637 (9)	0.00214 (6)	0.00417 (6)	0.00058 (6)
C(10)	0.01516 (9)	0.01987 (10)	0.01398 (9)	0.00219 (8)	0.00249 (6)	0.00240 (7)
C(12)	0.01654 (9)	0.01365 (8)	0.01274 (8)	−0.00182 (7)	0.00069 (6)	−0.00119 (6)
C(13)	0.01462 (8)	0.01503 (8)	0.01594 (9)	−0.00440 (7)	0.00298 (7)	−0.00381 (7)
C(14)	0.01431 (7)	0.00953 (6)	0.01184 (7)	−0.00147 (6)	0.00242 (5)	−0.00084 (5)

Geometric parameters (Å, º) top

S(1)—C(2)	1.7594 (3)	C(12)—C(13)	1.5404 (4)
S(1)—C(5)	1.7301 (3)	C(13)—C(14)	1.5050 (4)
S(11)—C(10)	1.8320 (4)	N(8)—H(8A)	1.0090
S(11)—C(12)	1.8131 (3)	N(8)—H(8B)	1.0090
S(17)—O(19)	1.4473 (3)	N(9)—H(9A)	1.0090
S(17)—O(20)	1.4397 (3)	N(9)—H(9B)	1.0090
S(17)—N(16)	1.6136 (2)	N(15)—H(15A)	1.0090
S(17)—N(18)	1.6311 (2)	N(15)—H(15B)	1.0090
N(3)—C(2)	1.3234 (4)	N(18)—H(18A)	1.0090
N(3)—C(4)	1.3858 (4)	N(18)—H(18B)	1.0090
N(6)—C(2)	1.3548 (4)	C(5)—H(5)	1.0830
N(6)—C(7)	1.3390 (3)	C(10)—H(10A)	1.0950
N(8)—C(7)	1.3392 (4)	C(10)—H(10B)	1.0950
N(9)—C(7)	1.3425 (4)	C(12)—H(12A)	1.0950
N(15)—C(14)	1.3223 (4)	C(12)—H(12B)	1.0950
N(16)—C(14)	1.3266 (3)	C(13)—H(13A)	1.0950
C(4)—C(5)	1.3654 (4)	C(13)—H(13B)	1.0950
C(4)—C(10)	1.4919 (4)

C(2)—S(1)—C(5)	89.671 (13)	C(7)—N(8)—H(8B)	119.95
C(10)—S(11)—C(12)	101.723 (13)	H(8A)—N(8)—H(8B)	119.87
O(19)—S(17)—O(20)	117.08 (2)	C(7)—N(9)—H(9A)	120.58
O(19)—S(17)—N(16)	111.654 (16)	C(7)—N(9)—H(9B)	117.97
O(19)—S(17)—N(18)	105.51 (2)	H(9A)—N(9)—H(9B)	121.10
O(20)—S(17)—N(16)	104.704 (18)	C(14)—N(15)—H(15A)	121.76
O(20)—S(17)—N(18)	111.381 (19)	C(14)—N(15)—H(15B)	117.11
N(16)—S(17)—N(18)	106.106 (12)	H(15A)—N(15)—H(15B)	121.05
C(2)—N(3)—C(4)	111.34 (2)	S(17)—N(18)—H(18A)	111.71
C(2)—N(6)—C(7)	120.42 (3)	S(17)—N(18)—H(18B)	114.42
S(17)—N(16)—C(14)	120.81 (2)	H(18A)—N(18)—H(18B)	112.29
S(1)—C(2)—N(3)	113.26 (2)	S(1)—C(5)—H(5)	125.11
S(1)—C(2)—N(6)	116.59 (2)	C(4)—C(5)—H(5)	124.92
N(3)—C(2)—N(6)	130.15 (3)	S(11)—C(10)—H(10A)	108.81
N(3)—C(4)—C(5)	115.72 (3)	S(11)—C(10)—H(10B)	108.99
N(3)—C(4)—C(10)	118.38 (2)	C(4)—C(10)—H(10A)	109.07
C(5)—C(4)—C(10)	125.90 (3)	C(4)—C(10)—H(10B)	108.84
S(1)—C(5)—C(4)	109.97 (2)	H(10A)—C(10)—H(10B)	107.68
N(6)—C(7)—N(8)	124.65 (3)	S(11)—C(12)—H(12A)	108.47
N(6)—C(7)—N(9)	117.51 (3)	S(11)—C(12)—H(12B)	108.62
N(8)—C(7)—N(9)	117.83 (3)	C(13)—C(12)—H(12A)	108.69
S(11)—C(10)—C(4)	113.31 (2)	C(13)—C(12)—H(12B)	108.67
S(11)—C(12)—C(13)	114.66 (2)	H(12A)—C(12)—H(12B)	107.51
C(12)—C(13)—C(14)	111.65 (2)	C(12)—C(13)—H(13A)	109.26
N(15)—C(14)—N(16)	127.23 (3)	C(12)—C(13)—H(13B)	109.37
N(15)—C(14)—C(13)	117.17 (2)	C(14)—C(13)—H(13A)	109.34
N(16)—C(14)—C(13)	115.56 (2)	C(14)—C(13)—H(13B)	109.31
C(7)—N(8)—H(8A)	120.14	H(13A)—C(13)—H(13B)	107.84

(famb) top

Crystal data top

C₈H₁₅N₇O₂S₃	F(000) = 504
M_r = 337.45	D_x = 1.561 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.7107 Å
Hall symbol: -P 2ybc	Cell parameters from 8948 reflections
a = 16.980 (2) Å	θ = 2.2–29.5°
b = 5.285 (1) Å	µ = 0.54 mm⁻¹
c = 17.639 (2) Å	T = 100 K
β = 116.416 (1)°	Block, white
V = 1418.0 (4) Å³	0.40 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker CCD area detector diffractometer	17385 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 60.0°, θ_min = 2.2°
ω–scans and π–scans	h = −41→37
70467 measured reflections	k = 0→12
21282 independent reflections	l = 0→43

Refinement top

Refinement on F	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.024	Riding
wR(F²) = 0.021	w = 1/[σ²(F_o²)]
S = 1.62	(Δ/σ)_max < 0.001
17385 reflections	Δρ_max = 0.36 e Å⁻³
459 parameters	Δρ_min = −0.27 e Å⁻³
1 restraint	Extinction correction: SHELXL, none
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0

Crystal data top

C₈H₁₅N₇O₂S₃	V = 1418.0 (4) Å³
M_r = 337.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.980 (2) Å	µ = 0.54 mm⁻¹
b = 5.285 (1) Å	T = 100 K
c = 17.639 (2) Å	0.40 × 0.30 × 0.25 mm
β = 116.416 (1)°

Data collection top

Bruker CCD area detector diffractometer	17385 reflections with I > 2σ(I)
70467 measured reflections	R_int = 0.025
21282 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	1 restraint
wR(F²) = 0.021	Riding
S = 1.62	Δρ_max = 0.36 e Å⁻³
17385 reflections	Δρ_min = −0.27 e Å⁻³
459 parameters

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S(1)	0.867925 (5)	0.033416 (14)	0.724949 (5)	0.015
S(11)	0.574210 (4)	0.230221 (13)	0.465606 (5)	0.013
S(17)	0.811208 (4)	0.136561 (12)	0.376405 (4)	0.010
O(19)	0.88904 (2)	0.05994 (8)	0.45002 (2)	0.015
O(20)	0.80780 (2)	0.07776 (7)	0.29470 (2)	0.015
N(3)	0.76934 (2)	0.35216 (5)	0.61233 (2)	0.013
N(6)	0.92556 (2)	0.40819 (6)	0.66020 (2)	0.015
N(8)	0.83836 (2)	0.68654 (6)	0.54881 (2)	0.014
N(9)	0.98867 (2)	0.71086 (12)	0.61104 (3)	0.030
N(15)	0.61229 (2)	0.17846 (6)	0.26752 (2)	0.014
N(16)	0.73205 (2)	0.00285 (5)	0.38788 (2)	0.013
N(18)	0.80726 (2)	0.44097 (5)	0.37908 (2)	0.015
C(2)	0.85278 (2)	0.29462 (5)	0.65851 (2)	0.012
C(4)	0.71446 (2)	0.18750 (5)	0.62646 (2)	0.013
C(5)	0.75520 (2)	0.00140 (6)	0.68423 (2)	0.016
C(7)	0.91587 (2)	0.59775 (6)	0.60691 (2)	0.015
C(10)	0.61732 (2)	0.22663 (7)	0.58035 (2)	0.016
C(12)	0.60209 (2)	−0.08930 (5)	0.44891 (2)	0.013
C(13)	0.58560 (2)	−0.12241 (6)	0.35702 (2)	0.014
C(14)	0.64808 (2)	0.03272 (5)	0.33575 (2)	0.011
H(8A)	0.78345	0.62922	0.55243	0.026
H(8B)	0.84168	0.85058	0.52111	0.030
H(9A)	0.98819	0.84405	0.56985	0.043
H(9B)	1.04610	0.61706	0.64125	0.054
H(15A)	0.54640	0.17297	0.23277	0.028
H(15B)	0.64932	0.27206	0.24509	0.027
H(18A)	0.76241	0.50583	0.32246	0.033
H(18B)	0.80700	0.50975	0.43233	0.033
H(5)	0.72190	−0.14469	0.70206	0.022
H(10A)	0.60094	0.40650	0.60072	0.023
H(10B)	0.58453	0.07559	0.59804	0.023
H(12A)	0.67139	−0.12669	0.49120	0.017
H(12B)	0.56208	−0.22504	0.46355	0.016
H(13A)	0.59287	−0.32262	0.34545	0.021
H(13B)	0.51789	−0.06654	0.31513	0.021

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S(1)	0.01489 (2)	0.01349 (2)	0.01206 (2)	0.00118 (2)	0.00514 (2)	0.00351 (2)
S(11)	0.01099 (2)	0.01157 (2)	0.01386 (2)	0.00004 (2)	0.00460 (2)	0.00019 (2)
S(17)	0.00776 (2)	0.01011 (2)	0.00880 (2)	−0.00033 (1)	0.00338 (1)	0.00064 (1)
O(19)	0.00820 (7)	0.01947 (12)	0.01366 (10)	−0.00016 (8)	0.00199 (7)	0.00574 (9)
O(20)	0.01492 (9)	0.01591 (10)	0.01202 (10)	0.00055 (8)	0.00749 (8)	−0.00216 (8)
N(3)	0.00894 (6)	0.01374 (7)	0.01269 (7)	−0.00110 (6)	0.00382 (5)	0.00281 (6)
N(6)	0.00833 (6)	0.01985 (9)	0.01396 (8)	−0.00051 (6)	0.00296 (6)	0.00628 (7)
N(8)	0.01184 (7)	0.01539 (9)	0.01215 (8)	0.00024 (7)	0.00442 (6)	0.00409 (6)
N(9)	0.01190 (9)	0.0409 (2)	0.02998 (18)	−0.00494 (12)	0.00586 (10)	0.01889 (17)
N(15)	0.00933 (6)	0.01675 (9)	0.01144 (8)	−0.00046 (6)	0.00328 (6)	0.00259 (6)
N(16)	0.00806 (6)	0.01426 (7)	0.01238 (7)	−0.00085 (5)	0.00366 (5)	0.00291 (6)
N(18)	0.01778 (9)	0.01034 (8)	0.01252 (8)	−0.00131 (7)	0.00554 (7)	−0.00085 (6)
C(2)	0.00926 (7)	0.01337 (8)	0.01078 (7)	−0.00047 (6)	0.00356 (6)	0.00227 (6)
C(4)	0.01094 (7)	0.01374 (8)	0.01179 (8)	−0.00275 (6)	0.00540 (6)	−0.00045 (6)
C(5)	0.01650 (9)	0.01368 (9)	0.01388 (9)	−0.00308 (8)	0.00741 (8)	0.00132 (7)
C(7)	0.00941 (7)	0.01923 (10)	0.01323 (9)	−0.00182 (7)	0.00369 (6)	0.00500 (8)
C(10)	0.01098 (8)	0.01891 (11)	0.01500 (10)	−0.00291 (8)	0.00691 (7)	−0.00223 (8)
C(12)	0.01116 (7)	0.01236 (8)	0.01350 (9)	0.00025 (6)	0.00630 (7)	0.00163 (6)
C(13)	0.01057 (7)	0.01417 (9)	0.01337 (9)	−0.00325 (7)	0.00534 (7)	−0.00073 (7)
C(14)	0.00826 (6)	0.01206 (7)	0.01037 (7)	−0.00095 (6)	0.00383 (6)	0.00023 (6)

Geometric parameters (Å, º) top

S(1)—C(2)	1.7542 (3)	C(12)—C(13)	1.5272 (4)
S(1)—C(5)	1.7278 (4)	C(13)—C(14)	1.5142 (4)
S(11)—C(10)	1.8205 (3)	N(8)—H(8A)	1.0090
S(11)—C(12)	1.8129 (3)	N(8)—H(8B)	1.0090
S(17)—O(19)	1.4387 (3)	N(9)—H(9A)	1.0090
S(17)—O(20)	1.4501 (3)	N(9)—H(9B)	1.0090
S(17)—N(16)	1.6090 (3)	N(15)—H(15A)	1.0090
S(17)—N(18)	1.6118 (3)	N(15)—H(15B)	1.0090
N(3)—C(2)	1.3177 (4)	N(18)—H(18A)	1.0090
N(3)—C(4)	1.3764 (4)	N(18)—H(18B)	1.0090
N(6)—C(2)	1.3622 (4)	C(5)—H(5)	1.0830
N(6)—C(7)	1.3329 (4)	C(10)—H(10A)	1.0950
N(8)—C(7)	1.3425 (4)	C(10)—H(10B)	1.0950
N(9)—C(7)	1.3457 (4)	C(12)—H(12A)	1.0950
N(15)—C(14)	1.3267 (4)	C(12)—H(12B)	1.0950
N(16)—C(14)	1.3179 (4)	C(13)—H(13A)	1.0950
C(4)—C(5)	1.3627 (4)	C(13)—H(13B)	1.0950
C(4)—C(10)	1.4938 (4)

C(2)—S(1)—C(5)	89.616 (14)	C(7)—N(8)—H(8B)	115.03
C(10)—S(11)—C(12)	99.556 (15)	H(8A)—N(8)—H(8B)	122.74
O(19)—S(17)—O(20)	116.82 (2)	C(7)—N(9)—H(9A)	123.91
O(19)—S(17)—N(16)	104.250 (16)	C(7)—N(9)—H(9B)	117.32
O(19)—S(17)—N(18)	106.74 (2)	H(9A)—N(9)—H(9B)	114.80
O(20)—S(17)—N(16)	111.389 (18)	C(14)—N(15)—H(15A)	118.11
O(20)—S(17)—N(18)	105.021 (19)	C(14)—N(15)—H(15B)	121.76
N(16)—S(17)—N(18)	112.752 (17)	H(15A)—N(15)—H(15B)	119.46
C(2)—N(3)—C(4)	111.75 (3)	S(17)—N(18)—H(18A)	109.45
C(2)—N(6)—C(7)	119.31 (3)	S(17)—N(18)—H(18B)	113.85
S(17)—N(16)—C(14)	124.38 (2)	H(18A)—N(18)—H(18B)	119.03
S(1)—C(2)—N(3)	113.10 (2)	S(1)—C(5)—H(5)	125.04
S(1)—C(2)—N(6)	118.04 (2)	C(4)—C(5)—H(5)	125.08
N(3)—C(2)—N(6)	128.85 (3)	S(11)—C(10)—H(10A)	108.70
N(3)—C(4)—C(5)	115.62 (3)	S(11)—C(10)—H(10B)	108.69
N(3)—C(4)—C(10)	119.11 (3)	C(4)—C(10)—H(10A)	108.76
C(5)—C(4)—C(10)	125.26 (3)	C(4)—C(10)—H(10B)	108.79
S(1)—C(5)—C(4)	109.88 (2)	H(10A)—C(10)—H(10B)	107.68
N(6)—C(7)—N(8)	124.93 (3)	S(11)—C(12)—H(12A)	109.67
N(6)—C(7)—N(9)	118.26 (3)	S(11)—C(12)—H(12B)	109.73
N(8)—C(7)—N(9)	116.81 (3)	C(13)—C(12)—H(12A)	109.66
S(11)—C(10)—C(4)	114.027 (19)	C(13)—C(12)—H(12B)	109.59
S(11)—C(12)—C(13)	109.96 (2)	H(12A)—C(12)—H(12B)	108.21
C(12)—C(13)—C(14)	112.53 (2)	C(12)—C(13)—H(13A)	109.02
N(15)—C(14)—N(16)	128.26 (3)	C(12)—C(13)—H(13B)	109.09
N(15)—C(14)—C(13)	116.77 (3)	C(14)—C(13)—H(13A)	109.11
N(16)—C(14)—C(13)	114.97 (2)	C(14)—C(13)—H(13B)	109.14
C(7)—N(8)—H(8A)	117.80	H(13A)—C(13)—H(13B)	107.85

Experimental details

	(fama)	(famb)
Crystal data
Chemical formula	C₈H₁₅N₇O₂S₃	C₈H₁₅N₇O₂S₃
M_r	337.45	337.45
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/n
Temperature (K)	100	100
a, b, c (Å)	11.9115 (3), 7.1876 (2), 16.6236 (4)	16.980 (2), 5.285 (1), 17.639 (2)
β (°)	100.045 (1)	116.416 (1)
V (Å³)	1401.4 (1)	1418.0 (4)
Z	4	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.54	0.54
Crystal size (mm)	0.35 × 0.35 × 0.30	0.40 × 0.30 × 0.25

Data collection
Diffractometer	Bruker CCD area detector diffractometer	Bruker CCD area detector diffractometer
Absorption correction	Analytical	–
T_min, T_max	0.787, 0.887	–
No. of measured, independent and observed [I > 2σ(I)] reflections	68907, 20197, 16610	70467, 21282, 17385
R_int	0.020	0.025
(sin θ/λ)_max (Å⁻¹)	1.212	1.219

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.021, 1.70	0.024, 0.021, 1.62
No. of reflections	16610	17385
No. of parameters	459	459
No. of restraints	1	1
H-atom treatment	Riding	Riding
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.28	0.36, −0.27

Selected geometric parameters (Å, º) for (fama) top

S(1)—C(2)	1.7594 (3)	N(6)—C(2)	1.3548 (4)
S(1)—C(5)	1.7301 (3)	N(6)—C(7)	1.3390 (3)
S(11)—C(10)	1.8320 (4)	N(8)—C(7)	1.3392 (4)
S(11)—C(12)	1.8131 (3)	N(9)—C(7)	1.3425 (4)
S(17)—O(19)	1.4473 (3)	N(15)—C(14)	1.3223 (4)
S(17)—O(20)	1.4397 (3)	N(16)—C(14)	1.3266 (3)
S(17)—N(16)	1.6136 (2)	C(4)—C(5)	1.3654 (4)
S(17)—N(18)	1.6311 (2)	C(4)—C(10)	1.4919 (4)
N(3)—C(2)	1.3234 (4)	C(12)—C(13)	1.5404 (4)
N(3)—C(4)	1.3858 (4)	C(13)—C(14)	1.5050 (4)

C(2)—S(1)—C(5)	89.671 (13)	N(3)—C(4)—C(5)	115.72 (3)
C(10)—S(11)—C(12)	101.723 (13)	N(3)—C(4)—C(10)	118.38 (2)
O(19)—S(17)—O(20)	117.08 (2)	C(5)—C(4)—C(10)	125.90 (3)
O(19)—S(17)—N(16)	111.654 (16)	S(1)—C(5)—C(4)	109.97 (2)
O(19)—S(17)—N(18)	105.51 (2)	N(6)—C(7)—N(8)	124.65 (3)
O(20)—S(17)—N(16)	104.704 (18)	N(6)—C(7)—N(9)	117.51 (3)
O(20)—S(17)—N(18)	111.381 (19)	N(8)—C(7)—N(9)	117.83 (3)
N(16)—S(17)—N(18)	106.106 (12)	S(11)—C(10)—C(4)	113.31 (2)
C(2)—N(3)—C(4)	111.34 (2)	S(11)—C(12)—C(13)	114.66 (2)
C(2)—N(6)—C(7)	120.42 (3)	C(12)—C(13)—C(14)	111.65 (2)
S(17)—N(16)—C(14)	120.81 (2)	N(15)—C(14)—N(16)	127.23 (3)
S(1)—C(2)—N(3)	113.26 (2)	N(15)—C(14)—C(13)	117.17 (2)
S(1)—C(2)—N(6)	116.59 (2)	N(16)—C(14)—C(13)	115.56 (2)
N(3)—C(2)—N(6)	130.15 (3)

Selected geometric parameters (Å, º) for (famb) top

S(1)—C(2)	1.7542 (3)	N(6)—C(2)	1.3622 (4)
S(1)—C(5)	1.7278 (4)	N(6)—C(7)	1.3329 (4)
S(11)—C(10)	1.8205 (3)	N(8)—C(7)	1.3425 (4)
S(11)—C(12)	1.8129 (3)	N(9)—C(7)	1.3457 (4)
S(17)—O(19)	1.4387 (3)	N(15)—C(14)	1.3267 (4)
S(17)—O(20)	1.4501 (3)	N(16)—C(14)	1.3179 (4)
S(17)—N(16)	1.6090 (3)	C(4)—C(5)	1.3627 (4)
S(17)—N(18)	1.6118 (3)	C(4)—C(10)	1.4938 (4)
N(3)—C(2)	1.3177 (4)	C(12)—C(13)	1.5272 (4)
N(3)—C(4)	1.3764 (4)	C(13)—C(14)	1.5142 (4)

C(2)—S(1)—C(5)	89.616 (14)	N(3)—C(4)—C(5)	115.62 (3)
C(10)—S(11)—C(12)	99.556 (15)	N(3)—C(4)—C(10)	119.11 (3)
O(19)—S(17)—O(20)	116.82 (2)	C(5)—C(4)—C(10)	125.26 (3)
O(19)—S(17)—N(16)	104.250 (16)	S(1)—C(5)—C(4)	109.88 (2)
O(19)—S(17)—N(18)	106.74 (2)	N(6)—C(7)—N(8)	124.93 (3)
O(20)—S(17)—N(16)	111.389 (18)	N(6)—C(7)—N(9)	118.26 (3)
O(20)—S(17)—N(18)	105.021 (19)	N(8)—C(7)—N(9)	116.81 (3)
N(16)—S(17)—N(18)	112.752 (17)	S(11)—C(10)—C(4)	114.027 (19)
C(2)—N(3)—C(4)	111.75 (3)	S(11)—C(12)—C(13)	109.96 (2)
C(2)—N(6)—C(7)	119.31 (3)	C(12)—C(13)—C(14)	112.53 (2)
S(17)—N(16)—C(14)	124.38 (2)	N(15)—C(14)—N(16)	128.26 (3)
S(1)—C(2)—N(3)	113.10 (2)	N(15)—C(14)—C(13)	116.77 (3)
S(1)—C(2)—N(6)	118.04 (2)	N(16)—C(14)—C(13)	114.97 (2)
N(3)—C(2)—N(6)	128.85 (3)

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