Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768105033689/lc5030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768105033689/lc5030sup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768105033689/lc5030sup3.pdf |
CCDC references: 298315; 298316; 298317
Data collection: SMART (Bruker, 2004) for 293K, (90K); Bruker SMART for WNT/2000 v5.629 for 100K. Cell refinement: SMART (Bruker, 2004) for 293K, (90K); Bruker SMART for WNT/2000 v5.629 for 100K. Data reduction: SMART (Bruker, 2004) for 293K, (90K); Bruker SAINT Version 6.45,1997-2003 for 100K. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for 293K, (90K); Bruker SHELXTL Version 6.14,2000-2003 for 100K. Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for 293K; Bruker SHELXTL Version 6.14,2000-2003 for 100K; Koritsanszky et al., (2003) for (90K). Molecular graphics: CAMERON (Watkin et al., 1996) for 293K; Bruker SHELXTL Version 6.14,2000-2003 for 100K; Koritsanszky et al., (2003) for (90K). Software used to prepare material for publication: PLATON (Spek, 2001) for 293K, (90K); Bruker SHELXTL Version 6.14,2000-2003 for 100K.
C2H5N3OS | F(000) = 248 |
Mr = 119.16 | Dx = 1.548 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3850 reflections |
a = 7.2569 (17) Å | θ = 2.8–26.4° |
b = 7.4263 (18) Å | µ = 0.51 mm−1 |
c = 9.593 (2) Å | T = 293 K |
β = 98.606 (4)° | Prism, colorless |
V = 511.2 (2) Å3 | 0.37 × 0.28 × 0.16 mm |
Z = 4 |
Bruker SMART APEX CCD area detector diffractometer | 1012 independent reflections |
Radiation source: fine-focus sealed tube | 961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ϕ & ω scans | θmax = 26.4°, θmin = 2.8° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −8→9 |
Tmin = 0.827, Tmax = 0.923 | k = −8→9 |
3850 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0429P)2 + 0.1699P] where P = (Fo2 + 2Fc2)/3 |
1012 reflections | (Δ/σ)max = 0.001 |
80 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
C2H5N3OS | V = 511.2 (2) Å3 |
Mr = 119.16 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2569 (17) Å | µ = 0.51 mm−1 |
b = 7.4263 (18) Å | T = 293 K |
c = 9.593 (2) Å | 0.37 × 0.28 × 0.16 mm |
β = 98.606 (4)° |
Bruker SMART APEX CCD area detector diffractometer | 1012 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 961 reflections with I > 2σ(I) |
Tmin = 0.827, Tmax = 0.923 | Rint = 0.014 |
3850 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.24 e Å−3 |
1012 reflections | Δρmin = −0.27 e Å−3 |
80 parameters |
Experimental. Crystal to Detector distance was 6.07 cm, ω range is 0.3 ° and exposure time was 15 s. |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.78081 (5) | 0.18924 (5) | 0.54094 (4) | 0.03944 (17) | |
C2 | 0.9854 (2) | 0.29268 (18) | 0.60197 (14) | 0.0286 (3) | |
N3 | 0.9916 (2) | 0.44516 (19) | 0.67164 (15) | 0.0395 (3) | |
N4 | 1.14576 (17) | 0.21758 (18) | 0.57826 (14) | 0.0340 (3) | |
N5 | 1.31717 (17) | 0.29497 (17) | 0.62762 (13) | 0.0347 (3) | |
H5 | 1.3606 | 0.3785 | 0.5796 | 0.042* | |
C6 | 1.4154 (2) | 0.2403 (2) | 0.74972 (16) | 0.0340 (3) | |
O7 | 1.35930 (16) | 0.13404 (17) | 0.82965 (12) | 0.0465 (3) | |
H3A | 0.888 (3) | 0.498 (3) | 0.6861 (19) | 0.052 (5)* | |
H3B | 1.091 (3) | 0.492 (3) | 0.702 (2) | 0.052 (6)* | |
H4 | 1.149 (3) | 0.116 (3) | 0.5415 (19) | 0.039 (5)* | |
H6 | 1.537 (3) | 0.297 (2) | 0.763 (2) | 0.046 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0244 (2) | 0.0430 (3) | 0.0486 (3) | 0.00265 (14) | −0.00218 (16) | −0.01180 (16) |
C2 | 0.0283 (7) | 0.0320 (7) | 0.0249 (6) | 0.0028 (5) | 0.0024 (5) | 0.0014 (5) |
N3 | 0.0311 (7) | 0.0377 (7) | 0.0490 (8) | 0.0015 (6) | 0.0035 (6) | −0.0126 (6) |
N4 | 0.0245 (6) | 0.0357 (7) | 0.0408 (7) | 0.0004 (5) | 0.0016 (5) | −0.0086 (6) |
N5 | 0.0250 (6) | 0.0412 (7) | 0.0380 (7) | −0.0058 (5) | 0.0055 (5) | 0.0043 (5) |
C6 | 0.0247 (7) | 0.0398 (8) | 0.0375 (8) | −0.0035 (6) | 0.0052 (6) | −0.0039 (7) |
O7 | 0.0417 (6) | 0.0565 (7) | 0.0401 (6) | −0.0130 (6) | 0.0026 (5) | 0.0082 (5) |
S1—C2 | 1.6959 (15) | N4—H4 | 0.83 (2) |
C2—N3 | 1.312 (2) | N5—C6 | 1.340 (2) |
C2—N4 | 1.3405 (19) | N5—H5 | 0.8600 |
N3—H3A | 0.88 (2) | C6—O7 | 1.212 (2) |
N3—H3B | 0.82 (2) | C6—H6 | 0.97 (2) |
N4—N5 | 1.3876 (17) | ||
N3—C2—N4 | 118.74 (14) | N5—N4—H4 | 116.2 (13) |
N3—C2—S1 | 121.89 (12) | C6—N5—N4 | 120.36 (13) |
N4—C2—S1 | 119.37 (11) | C6—N5—H5 | 119.8 |
C2—N3—H3A | 120.0 (13) | N4—N5—H5 | 119.8 |
C2—N3—H3B | 121.0 (14) | O7—C6—N5 | 124.40 (14) |
H3A—N3—H3B | 119 (2) | O7—C6—H6 | 125.5 (12) |
C2—N4—N5 | 121.78 (13) | N5—C6—H6 | 110.1 (12) |
C2—N4—H4 | 121.7 (13) |
C2H5N3OS | F(000) = 248 |
Mr = 119.15 | Dx = 1.583 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 4707 reflections |
a = 7.2339 (5) Å | θ = 2.8–26.0° |
b = 7.3703 (5) Å | µ = 0.52 mm−1 |
c = 9.4771 (7) Å | T = 100 K |
β = 98.426 (1)° | Block, colorless |
V = 499.83 (6) Å3 | 0.28 × 0.25 × 0.16 mm |
Z = 4 |
CCD area detector diffractometer | 982 independent reflections |
Radiation source: fine-focus sealed tube | 953 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
phi and ω scans | θmax = 26.0°, θmin = 2.9° |
Absorption correction: multi-scan SADABS | h = −8→8 |
Tmin = 0.868, Tmax = 0.922 | k = −9→9 |
6106 measured reflections | l = −11→11 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0381P)2 + 0.2485P] where P = (Fo2 + 2Fc2)/3 |
982 reflections | (Δ/σ)max < 0.001 |
80 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C2H5N3OS | V = 499.83 (6) Å3 |
Mr = 119.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2339 (5) Å | µ = 0.52 mm−1 |
b = 7.3703 (5) Å | T = 100 K |
c = 9.4771 (7) Å | 0.28 × 0.25 × 0.16 mm |
β = 98.426 (1)° |
CCD area detector diffractometer | 982 independent reflections |
Absorption correction: multi-scan SADABS | 953 reflections with I > 2σ(I) |
Tmin = 0.868, Tmax = 0.922 | Rint = 0.017 |
6106 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.065 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.20 e Å−3 |
982 reflections | Δρmin = −0.26 e Å−3 |
80 parameters |
Experimental. X-ray data were collected at 100 K with phi and omega scan. stratigy of the data collection was done using COSMO supplied by BRUKER AXS. |
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. |
x | y | z | Uiso*/Ueq | ||
C2 | 0.51400 (18) | 0.29455 (17) | 0.39851 (13) | 0.0128 (3) | |
C6 | 0.08200 (17) | 0.23961 (18) | 0.24985 (14) | 0.0145 (3) | |
N4 | 0.35312 (15) | 0.21776 (16) | 0.42325 (12) | 0.0145 (3) | |
N5 | 0.18118 (16) | 0.29668 (15) | 0.37321 (12) | 0.0146 (3) | |
N3 | 0.50740 (17) | 0.44900 (16) | 0.32790 (12) | 0.0161 (3) | |
O7 | 0.13925 (13) | 0.13081 (13) | 0.16897 (10) | 0.0187 (2) | |
S1 | 0.72032 (4) | 0.19016 (4) | 0.45953 (3) | 0.01576 (14) | |
H3A | 0.612 (3) | 0.499 (2) | 0.3145 (17) | 0.024* | |
H3B | 0.404 (3) | 0.498 (2) | 0.2971 (18) | 0.024* | |
H4 | 0.350 (2) | 0.115 (3) | 0.4623 (19) | 0.024* | |
H5 | 0.134 (3) | 0.349 (2) | 0.427 (2) | 0.024* | |
H6 | −0.041 (3) | 0.297 (2) | 0.2348 (19) | 0.021 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0146 (6) | 0.0141 (6) | 0.0095 (6) | −0.0009 (4) | 0.0010 (5) | −0.0025 (5) |
C6 | 0.0121 (6) | 0.0154 (6) | 0.0164 (6) | 0.0002 (5) | 0.0028 (5) | 0.0034 (5) |
N4 | 0.0111 (5) | 0.0148 (5) | 0.0172 (6) | 0.0006 (4) | 0.0004 (4) | 0.0037 (4) |
N5 | 0.0116 (6) | 0.0169 (6) | 0.0154 (6) | 0.0035 (4) | 0.0029 (4) | −0.0019 (4) |
N3 | 0.0130 (5) | 0.0158 (6) | 0.0194 (6) | −0.0001 (4) | 0.0016 (4) | 0.0043 (4) |
O7 | 0.0189 (5) | 0.0212 (5) | 0.0160 (5) | 0.0038 (4) | 0.0028 (4) | −0.0023 (4) |
S1 | 0.0112 (2) | 0.0163 (2) | 0.0190 (2) | −0.00057 (11) | −0.00037 (13) | 0.00372 (11) |
C2—N3 | 1.3178 (17) | N4—N5 | 1.3919 (16) |
C2—N4 | 1.3452 (18) | N4—H4 | 0.84 (2) |
C2—S1 | 1.7032 (13) | N5—H5 | 0.764 (19) |
C6—O7 | 1.2228 (17) | N3—H3A | 0.869 (19) |
C6—N5 | 1.3464 (17) | N3—H3B | 0.843 (18) |
C6—H6 | 0.974 (18) | ||
N3—C2—N4 | 118.95 (12) | N5—N4—H4 | 116.4 (12) |
N3—C2—S1 | 121.83 (10) | C6—N5—N4 | 120.08 (11) |
N4—C2—S1 | 119.22 (10) | C6—N5—H5 | 120.6 (14) |
O7—C6—N5 | 124.25 (12) | N4—N5—H5 | 116.7 (14) |
O7—C6—H6 | 125.2 (10) | C2—N3—H3A | 118.4 (12) |
N5—C6—H6 | 110.5 (10) | C2—N3—H3B | 120.9 (12) |
C2—N4—N5 | 121.17 (11) | H3A—N3—H3B | 120.7 (17) |
C2—N4—H4 | 122.2 (12) |
C2H5N3OS | F(000) = 248 |
Mr = 119.16 | Dx = 1.583 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 24842 reflections |
a = 7.2359 (3) Å | θ = 2.8–50.3° |
b = 7.3713 (3) Å | µ = 0.52 mm−1 |
c = 9.4768 (4) Å | T = 90 K |
β = 98.403 (2)° | Prism, colorless |
V = 500.05 (4) Å3 | 0.37 × 0.28 × 0.16 mm |
Z = 4 |
Bruker SMART APEX CCD area detector diffractometer | 5136 independent reflections |
Radiation source: fine-focus sealed tube | 4514 reflections with > 3σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ & ω scans | θmax = 50.3°, θmin = 2.8° |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | h = −15→15 |
Tmin = 0.826, Tmax = 0.920 | k = −15→15 |
24842 measured reflections | l = −19→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.014 | All H-atom parameters refined |
wR(F2) = 0.015 | w2 = 1/[s2(Fo2)] |
S = 1.56 | (Δ/σ)max < 0.001 |
4518 reflections | Δρmax = 0.30 e Å−3 |
207 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Absolute structure: unk |
Primary atom site location: structure-invariant direct methods |
C2H5N3OS | V = 500.05 (4) Å3 |
Mr = 119.16 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2359 (3) Å | µ = 0.52 mm−1 |
b = 7.3713 (3) Å | T = 90 K |
c = 9.4768 (4) Å | 0.37 × 0.28 × 0.16 mm |
β = 98.403 (2)° |
Bruker SMART APEX CCD area detector diffractometer | 5136 independent reflections |
Absorption correction: multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | 4514 reflections with > 3σ(I) |
Tmin = 0.826, Tmax = 0.920 | Rint = 0.025 |
24842 measured reflections |
R[F2 > 2σ(F2)] = 0.014 | 0 restraints |
wR(F2) = 0.015 | All H-atom parameters refined |
S = 1.56 | Δρmax = 0.30 e Å−3 |
4518 reflections | Δρmin = −0.25 e Å−3 |
207 parameters | Absolute structure: unk |
Experimental. Crystal to Detector distance was 6.07 cm, ω range is 0.3 ° and exposure time was 20 s, 40 s and 60 s in three batches respectively. |
Refinement. Multipole Refinement |
x | y | z | Uiso*/Ueq | ||
S(1) | 0.279680 (6) | 0.809654 (6) | 0.540387 (5) | 0.012 | |
O(7) | 0.86115 (3) | 0.86953 (3) | 0.83120 (2) | 0.015 | |
N(3) | 0.49275 (3) | 0.55014 (3) | 0.67235 (2) | 0.013 | |
N(4) | 0.64756 (3) | 0.78212 (3) | 0.57685 (2) | 0.011 | |
N(5) | 0.81864 (3) | 0.70289 (3) | 0.62614 (2) | 0.011 | |
C(2) | 0.48613 (3) | 0.70517 (2) | 0.60133 (2) | 0.009 | |
C(6) | 0.91839 (3) | 0.76004 (3) | 0.75009 (2) | 0.011 | |
H(3A) | 0.36982 | 0.48844 | 0.68842 | 0.017 (2) | |
H(3B) | 0.61594 | 0.48849 | 0.71535 | 0.026 (2) | |
H(4) | 0.65368 | 0.90756 | 0.52988 | 0.018 (2) | |
H(5) | 0.88850 | 0.63714 | 0.55385 | 0.025 (2) | |
H(6) | 1.05545 | 0.69726 | 0.76793 | 0.024 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S(1) | 0.00820 (2) | 0.01222 (2) | 0.01441 (2) | −0.00066 (1) | −0.00030 (1) | 0.00314 (1) |
O(7) | 0.01408 (7) | 0.01745 (7) | 0.01231 (6) | 0.00399 (5) | 0.00115 (5) | −0.00283 (5) |
N(3) | 0.01117 (6) | 0.01150 (6) | 0.01571 (7) | −0.00060 (5) | 0.00144 (5) | 0.00438 (5) |
N(4) | 0.00825 (6) | 0.01140 (6) | 0.01393 (6) | −0.00068 (4) | 0.00101 (5) | 0.00284 (5) |
N(5) | 0.00880 (6) | 0.01345 (6) | 0.01193 (6) | 0.00144 (5) | 0.00142 (5) | −0.00153 (5) |
C(2) | 0.00872 (6) | 0.00979 (5) | 0.00950 (6) | −0.00057 (4) | 0.00073 (4) | 0.00077 (4) |
C(6) | 0.00924 (6) | 0.01308 (6) | 0.01119 (6) | 0.00180 (5) | 0.00138 (5) | −0.00013 (5) |
S(1)—C(2) | 1.7048 (2) | N(4)—C(2) | 1.3487 (3) |
O(7)—C(6) | 1.2275 (3) | N(4)—H(4) | 1.0300 |
N(3)—C(2) | 1.3235 (3) | N(5)—C(6) | 1.3529 (3) |
N(3)—H(3A) | 1.0300 | N(5)—H(5) | 1.0300 |
N(3)—H(3B) | 1.0300 | C(6)—H(6) | 1.0850 |
N(4)—N(5) | 1.3866 (3) | ||
C(2)—N(3)—H(3A) | 119.250 | C(6)—N(5)—H(5) | 118.201 |
C(2)—N(3)—H(3B) | 123.161 | S(1)—C(2)—N(3) | 121.812 (15) |
H(3A)—N(3)—H(3B) | 117.570 | S(1)—C(2)—N(4) | 119.327 (14) |
N(5)—N(4)—C(2) | 121.194 (18) | N(3)—C(2)—N(4) | 118.861 (18) |
N(5)—N(4)—H(4) | 115.534 | O(7)—C(6)—N(5) | 124.219 (19) |
C(2)—N(4)—H(4) | 123.015 | O(7)—C(6)—H(6) | 124.56 |
N(4)—N(5)—C(6) | 119.873 (18) | N(5)—C(6)—H(6) | 111.222 |
N(4)—N(5)—H(5) | 118.352 | ||
H(3A)—N(3)—C(2)—S(1) | 2.10 | H(4)—N(4)—N(5)—C(6) | 77.40 |
H(3A)—N(3)—C(2)—N(4) | −177.90 | H(4)—N(4)—N(5)—H(5) | −80.90 |
H(3B)—N(3)—C(2)—S(1) | −176.20 | H(4)—N(4)—C(2)—S(1) | 5.20 |
H(3B)—N(3)—C(2)—N(4) | 3.70 | H(4)—N(4)—C(2)—N(3) | −174.70 |
N(5)—N(4)—C(2)—S(1) | 179.17 (1) | N(4)—N(5)—C(6)—O(7) | 6.50 (3) |
N(5)—N(4)—C(2)—N(3) | −0.80 (2) | N(4)—N(5)—C(6)—H(6) | −173.10 |
C(2)—N(4)—N(5)—C(6) | −96.90 (2) | H(5)—N(5)—C(6)—O(7) | 164.80 |
C(2)—N(4)—N(5)—H(5) | 104.80 | H(5)—N(5)—C(6)—H(6) | −14.80 |
Experimental details
(293K) | (100K) | (90K) | |
Crystal data | |||
Chemical formula | C2H5N3OS | C2H5N3OS | C2H5N3OS |
Mr | 119.16 | 119.15 | 119.16 |
Crystal system, space group | Monoclinic, P21/c | Monoclinic, P21/c | Monoclinic, P21/c |
Temperature (K) | 293 | 100 | 90 |
a, b, c (Å) | 7.2569 (17), 7.4263 (18), 9.593 (2) | 7.2339 (5), 7.3703 (5), 9.4771 (7) | 7.2359 (3), 7.3713 (3), 9.4768 (4) |
α, β, γ (°) | 90, 98.606 (4), 90 | 90, 98.426 (1), 90 | 90, 98.403 (2), 90 |
V (Å3) | 511.2 (2) | 499.83 (6) | 500.05 (4) |
Z | 4 | 4 | 4 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.51 | 0.52 | 0.52 |
Crystal size (mm) | 0.37 × 0.28 × 0.16 | 0.28 × 0.25 × 0.16 | 0.37 × 0.28 × 0.16 |
Data collection | |||
Diffractometer | Bruker SMART APEX CCD area detector diffractometer | CCD area detector diffractometer | Bruker SMART APEX CCD area detector diffractometer |
Absorption correction | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 | Multi-scan SADABS | Multi-scan R.H. Blessing, Acta Cryst. (1995), A51, 33-38 |
Tmin, Tmax | 0.827, 0.923 | 0.868, 0.922 | 0.826, 0.920 |
No. of measured, independent and observed reflections | 3850, 1012, 961 [I > 2σ(I)] | 6106, 982, 953 [I > 2σ(I)] | 24842, 5136, 4514 [ > 3σ(I)] |
Rint | 0.014 | 0.017 | 0.025 |
(sin θ/λ)max (Å−1) | 0.625 | 0.617 | 1.083 |
Refinement | |||
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.076, 1.08 | 0.025, 0.065, 1.08 | 0.014, 0.015, 1.56 |
No. of reflections | 1012 | 982 | 4518 |
No. of parameters | 80 | 80 | 207 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.24, −0.27 | 0.20, −0.26 | 0.30, −0.25 |
Absolute structure | ? | ? | Unk |
Computer programs: SMART (Bruker, 2004), Bruker SMART for WNT/2000 v5.629, Bruker SAINT Version 6.45,1997-2003, SHELXS97 (Sheldrick, 1997), Bruker SHELXTL Version 6.14,2000-2003, SHELXL97 (Sheldrick, 1997), Koritsanszky et al., (2003), CAMERON (Watkin et al., 1996), PLATON (Spek, 2001).
S(1)—C(2) | 1.7048 (2) | N(4)—C(2) | 1.3487 (3) |
O(7)—C(6) | 1.2275 (3) | N(4)—H(4) | 1.0300 |
N(3)—C(2) | 1.3235 (3) | N(5)—C(6) | 1.3529 (3) |
N(3)—H(3A) | 1.0300 | N(5)—H(5) | 1.0300 |
N(3)—H(3B) | 1.0300 | C(6)—H(6) | 1.0850 |
N(4)—N(5) | 1.3866 (3) | ||
C(2)—N(3)—H(3A) | 119.250 | C(6)—N(5)—H(5) | 118.201 |
C(2)—N(3)—H(3B) | 123.161 | S(1)—C(2)—N(3) | 121.812 (15) |
H(3A)—N(3)—H(3B) | 117.570 | S(1)—C(2)—N(4) | 119.327 (14) |
N(5)—N(4)—C(2) | 121.194 (18) | N(3)—C(2)—N(4) | 118.861 (18) |
N(5)—N(4)—H(4) | 115.534 | O(7)—C(6)—N(5) | 124.219 (19) |
C(2)—N(4)—H(4) | 123.015 | O(7)—C(6)—H(6) | 124.56 |
N(4)—N(5)—C(6) | 119.873 (18) | N(5)—C(6)—H(6) | 111.222 |
N(4)—N(5)—H(5) | 118.352 | ||
H(3A)—N(3)—C(2)—S(1) | 2.10 | H(4)—N(4)—N(5)—C(6) | 77.40 |
H(3A)—N(3)—C(2)—N(4) | −177.90 | H(4)—N(4)—N(5)—H(5) | −80.90 |
H(3B)—N(3)—C(2)—S(1) | −176.20 | H(4)—N(4)—C(2)—S(1) | 5.20 |
H(3B)—N(3)—C(2)—N(4) | 3.70 | H(4)—N(4)—C(2)—N(3) | −174.70 |
N(5)—N(4)—C(2)—S(1) | 179.17 (1) | N(4)—N(5)—C(6)—O(7) | 6.50 (3) |
N(5)—N(4)—C(2)—N(3) | −0.80 (2) | N(4)—N(5)—C(6)—H(6) | −173.10 |
C(2)—N(4)—N(5)—C(6) | −96.90 (2) | H(5)—N(5)—C(6)—O(7) | 164.80 |
C(2)—N(4)—N(5)—H(5) | 104.80 | H(5)—N(5)—C(6)—H(6) | −14.80 |