journal menu
research papers
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.
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.Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S0108767304017891/xc5012sup1.cif |
 | Portable Document Format (PDF) file https://doi.org/10.1107/S0108767304017891/xc5012sup2.pdf |
 | Structure factor file (CIF format) https://doi.org/10.1107/S0108767304017891/xc5012famasup3.fcf |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108767304017891/xc5012fambsup4.fcf |
CCDC references: 215086; 215087
Computing details top
![[Figure 1]](https://journals.iucr.org/a/issues/2004/05/00/xc5012/xc5012fig1thm.gif)
![[Figure 2]](https://journals.iucr.org/a/issues/2004/05/00/xc5012/xc5012fig2thm.gif)
![[Figure 3]](https://journals.iucr.org/a/issues/2004/05/00/xc5012/xc5012fig3thm.gif)
(fama) top
Crystal data top
| C8H15N7O2S3 | F(000) = 504 |
| Mr = 337.45 | Dx = 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 | Rint = 0.020 |
| ω–scans and π–scans | θmax = 59.5°, θmin = 1.8° |
| Absorption correction: analytical ? | h = −28→28 |
| Tmin = 0.787, Tmax = 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(Fo2)] |
| S = 1.70 | (Δ/σ)max < 0.001 |
| 16610 reflections | Δρmax = 0.29 e Å−3 |
| 459 parameters | Δρmin = −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 |
| Mr = 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) |
| Tmin = 0.787, Tmax = 0.887 | Rint = 0.020 |
| 68907 measured reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.023 | 1 restraint |
| wR(F2) = 0.021 | Riding |
| S = 1.70 | Δρmax = 0.29 e Å−3 |
| 16610 reflections | Δρmin = −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 | Uiso*/Ueq | ||
| 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 |
| Mr = 337.45 | Dx = 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 | Rint = 0.025 |
| Graphite monochromator | θmax = 60.0°, θmin = 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(Fo2)] |
| S = 1.62 | (Δ/σ)max < 0.001 |
| 17385 reflections | Δρmax = 0.36 e Å−3 |
| 459 parameters | Δρmin = −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 |
| Mr = 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 | Rint = 0.025 |
| 21282 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.024 | 1 restraint |
| wR(F2) = 0.021 | Riding |
| S = 1.62 | Δρmax = 0.36 e Å−3 |
| 17385 reflections | Δρmin = −0.27 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 | Uiso*/Ueq | ||
| 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 |
| Mr | 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 | – |
| Tmin, Tmax | 0.787, 0.887 | – |
| No. of measured, independent and observed [I > 2σ(I)] reflections | 68907, 20197, 16610 | 70467, 21282, 17385 |
| Rint | 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 |
| Δρmax, Δρmin (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) |
