Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057364/hb2651sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057364/hb2651Isup2.hkl |
CCDC reference: 672926
Key indicators
- Single-crystal X-ray study
- T = 223 K
- Mean (C-C) = 0.005 Å
- R factor = 0.060
- wR factor = 0.168
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C10A - C15A .. 7.17 su
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.77 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.99 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.36 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10A PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.51 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT420_ALERT_2_C D-H Without Acceptor N1 - H1 ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2A - H2A ... ? PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CG(C2-C PLAT717_ALERT_1_C D...A Unknown or Inconsistent Label .......... CG(C9-C PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 11 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Ho et al. (2005, 2006); Ho & Tiekink (2007); Kuan et al. (2007); Spek (2003). For related structures, see: Prisyazhnyuk et al. (1986).
Colourless prisms of (I) was isolated as the unexpected product from the recrystallization from a 1:2 CH2Cl2/Et2O solution of an authenticated sample of MeOC(=S)N(H)(C6H4Me-2); m. p. 456–458 K. Analysis found: C 70.36, H 5.98, N 11.68, S 12.46%; C15H16N2S requires: C 70.28, H 6.30, N 10.94, S 12.48%.
All H atoms were included in the riding-model approximation, with C—H = 0.94 to 0.97 Å and N—H = 0.87 Å, and with Uiso(H) = 1.5Ueq(methyl-C) or 1.2Ueq(N and remaining-C).
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97.
Fig. 1. Dimer formation in (I) mediated by N—H···S hydrogen bonding (dashed lines) Displacement ellipsoids are shown at the 50% probability level for the non-hydrogen atoms. |
C15H16N2S | F(000) = 1088 |
Mr = 256.37 | Dx = 1.221 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 2837 reflections |
a = 12.4391 (6) Å | θ = 2.3–23.1° |
b = 9.5274 (4) Å | µ = 0.22 mm−1 |
c = 23.5683 (11) Å | T = 223 K |
β = 93.347 (1)° | Prism, colourless |
V = 2788.4 (2) Å3 | 0.30 × 0.08 × 0.08 mm |
Z = 8 |
Bruker AXS SMART CCD diffractometer | 3835 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.048 |
Graphite monochromator | θmax = 26.5°, θmin = 1.8° |
ω and ϕ scans | h = −15→15 |
21083 measured reflections | k = −11→11 |
5782 independent reflections | l = −29→28 |
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)] = 0.060 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0792P)2 + 1.2902P] where P = (Fo2 + 2Fc2)/3 |
5782 reflections | (Δ/σ)max < 0.001 |
329 parameters | Δρmax = 0.83 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
C15H16N2S | V = 2788.4 (2) Å3 |
Mr = 256.37 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.4391 (6) Å | µ = 0.22 mm−1 |
b = 9.5274 (4) Å | T = 223 K |
c = 23.5683 (11) Å | 0.30 × 0.08 × 0.08 mm |
β = 93.347 (1)° |
Bruker AXS SMART CCD diffractometer | 3835 reflections with I > 2σ(I) |
21083 measured reflections | Rint = 0.048 |
5782 independent reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.83 e Å−3 |
5782 reflections | Δρmin = −0.30 e Å−3 |
329 parameters |
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 | 0.21259 (5) | 0.51621 (7) | 0.59570 (4) | 0.0468 (2) | |
S1A | 0.48412 (5) | 0.25241 (7) | 0.65222 (4) | 0.0462 (2) | |
N1 | 0.05247 (17) | 0.3503 (2) | 0.62329 (11) | 0.0471 (6) | |
H1 | 0.0276 | 0.2671 | 0.6303 | 0.057* | |
N1A | 0.48194 (17) | 0.5083 (2) | 0.60848 (10) | 0.0414 (6) | |
H1A | 0.4127 | 0.5017 | 0.6115 | 0.050* | |
N2 | 0.22072 (17) | 0.2525 (2) | 0.63017 (11) | 0.0423 (6) | |
H2 | 0.2886 | 0.2582 | 0.6235 | 0.051* | |
N2A | 0.64910 (17) | 0.4149 (2) | 0.62999 (11) | 0.0480 (6) | |
H2A | 0.6753 | 0.4957 | 0.6205 | 0.058* | |
C1 | 0.1589 (2) | 0.3653 (3) | 0.61774 (12) | 0.0388 (6) | |
C2 | −0.0217 (2) | 0.4655 (3) | 0.61817 (13) | 0.0405 (7) | |
C3 | −0.0426 (2) | 0.5411 (3) | 0.66658 (13) | 0.0449 (7) | |
C4 | −0.1156 (2) | 0.6516 (3) | 0.66026 (15) | 0.0533 (8) | |
H4 | −0.1315 | 0.7050 | 0.6923 | 0.064* | |
C5 | −0.1648 (2) | 0.6843 (3) | 0.60836 (16) | 0.0566 (9) | |
H5 | −0.2135 | 0.7596 | 0.6052 | 0.068* | |
C6 | −0.1433 (2) | 0.6074 (4) | 0.56081 (16) | 0.0571 (9) | |
H6 | −0.1768 | 0.6301 | 0.5252 | 0.069* | |
C7 | −0.0719 (2) | 0.4964 (3) | 0.56622 (13) | 0.0496 (7) | |
H7 | −0.0577 | 0.4419 | 0.5343 | 0.059* | |
C8 | 0.0099 (3) | 0.5040 (4) | 0.72243 (15) | 0.0713 (10) | |
H8A | −0.0038 | 0.4061 | 0.7306 | 0.107* | |
H8B | −0.0188 | 0.5624 | 0.7517 | 0.107* | |
H8C | 0.0869 | 0.5193 | 0.7216 | 0.107* | |
C9 | 0.1835 (2) | 0.1231 (3) | 0.65374 (13) | 0.0406 (7) | |
C10 | 0.1436 (2) | 0.0169 (3) | 0.61827 (14) | 0.0526 (8) | |
C11 | 0.1133 (3) | −0.1082 (3) | 0.64431 (18) | 0.0624 (10) | |
H11 | 0.0871 | −0.1829 | 0.6214 | 0.075* | |
C12 | 0.1206 (3) | −0.1244 (3) | 0.70169 (19) | 0.0633 (10) | |
H12 | 0.0982 | −0.2088 | 0.7179 | 0.076* | |
C13 | 0.1602 (3) | −0.0190 (4) | 0.73586 (17) | 0.0669 (10) | |
H13 | 0.1657 | −0.0310 | 0.7755 | 0.080* | |
C14 | 0.1921 (2) | 0.1051 (3) | 0.71226 (14) | 0.0521 (8) | |
H14 | 0.2199 | 0.1778 | 0.7358 | 0.063* | |
C15 | 0.1322 (4) | 0.0374 (5) | 0.55485 (17) | 0.0919 (14) | |
H15A | 0.0868 | 0.1182 | 0.5461 | 0.138* | |
H15B | 0.0997 | −0.0456 | 0.5372 | 0.138* | |
H15C | 0.2027 | 0.0526 | 0.5404 | 0.138* | |
C1A | 0.5417 (2) | 0.4002 (3) | 0.62866 (12) | 0.0381 (6) | |
C2A | 0.5197 (2) | 0.6334 (3) | 0.58252 (12) | 0.0381 (6) | |
C3A | 0.4924 (2) | 0.7635 (3) | 0.60450 (13) | 0.0446 (7) | |
C4A | 0.5293 (3) | 0.8814 (3) | 0.57692 (16) | 0.0572 (9) | |
H4A | 0.5135 | 0.9708 | 0.5911 | 0.069* | |
C5A | 0.5880 (3) | 0.8715 (3) | 0.52955 (17) | 0.0611 (9) | |
H5A | 0.6118 | 0.9535 | 0.5120 | 0.073* | |
C6A | 0.6121 (2) | 0.7436 (3) | 0.50779 (14) | 0.0515 (8) | |
H6A | 0.6511 | 0.7371 | 0.4749 | 0.062* | |
C7A | 0.5786 (2) | 0.6239 (3) | 0.53434 (13) | 0.0436 (7) | |
H7A | 0.5957 | 0.5353 | 0.5198 | 0.052* | |
C8A | 0.4253 (3) | 0.7755 (3) | 0.65496 (15) | 0.0618 (9) | |
H8A1 | 0.4215 | 0.8731 | 0.6664 | 0.093* | |
H8A2 | 0.4577 | 0.7204 | 0.6861 | 0.093* | |
H8A3 | 0.3533 | 0.7409 | 0.6451 | 0.093* | |
C9A | 0.7228 (2) | 0.3044 (3) | 0.64629 (17) | 0.0567 (9) | |
C10A | 0.7556 (3) | 0.2133 (4) | 0.6045 (2) | 0.0715 (11) | |
C11A | 0.8274 (3) | 0.1092 (4) | 0.6208 (3) | 0.1027 (19) | |
H11A | 0.8501 | 0.0459 | 0.5933 | 0.123* | |
C12A | 0.8662 (3) | 0.0954 (5) | 0.6750 (4) | 0.114 (2) | |
H12A | 0.9154 | 0.0233 | 0.6847 | 0.137* | |
C13A | 0.8340 (3) | 0.1876 (5) | 0.7175 (3) | 0.1037 (18) | |
H13A | 0.8611 | 0.1768 | 0.7553 | 0.124* | |
C14A | 0.7603 (3) | 0.2971 (4) | 0.7027 (2) | 0.0811 (13) | |
H14A | 0.7381 | 0.3615 | 0.7299 | 0.097* | |
C15A | 0.7149 (4) | 0.2298 (5) | 0.5462 (3) | 0.1119 (18) | |
H15D | 0.7339 | 0.3221 | 0.5327 | 0.168* | |
H15E | 0.6372 | 0.2197 | 0.5440 | 0.168* | |
H15F | 0.7464 | 0.1586 | 0.5229 | 0.168* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0322 (4) | 0.0379 (4) | 0.0707 (5) | −0.0050 (3) | 0.0051 (3) | 0.0105 (4) |
S1A | 0.0337 (4) | 0.0340 (4) | 0.0716 (5) | −0.0025 (3) | 0.0081 (3) | 0.0114 (3) |
N1 | 0.0284 (11) | 0.0317 (12) | 0.0820 (19) | −0.0045 (9) | 0.0103 (11) | 0.0040 (12) |
N1A | 0.0288 (11) | 0.0326 (12) | 0.0632 (16) | −0.0018 (9) | 0.0062 (10) | 0.0072 (11) |
N2 | 0.0276 (11) | 0.0335 (12) | 0.0665 (16) | −0.0032 (9) | 0.0083 (10) | 0.0029 (11) |
N2A | 0.0302 (12) | 0.0344 (12) | 0.0796 (18) | −0.0045 (10) | 0.0029 (11) | 0.0139 (12) |
C1 | 0.0331 (14) | 0.0370 (14) | 0.0463 (16) | −0.0054 (11) | 0.0042 (11) | −0.0039 (13) |
C2 | 0.0260 (13) | 0.0355 (14) | 0.0605 (19) | −0.0051 (11) | 0.0082 (12) | 0.0018 (13) |
C3 | 0.0381 (15) | 0.0385 (15) | 0.0581 (19) | −0.0094 (12) | 0.0020 (13) | 0.0016 (14) |
C4 | 0.0422 (16) | 0.0413 (16) | 0.077 (2) | −0.0062 (13) | 0.0119 (15) | −0.0131 (16) |
C5 | 0.0339 (15) | 0.0465 (18) | 0.089 (3) | 0.0005 (13) | 0.0020 (16) | 0.0068 (18) |
C6 | 0.0340 (15) | 0.066 (2) | 0.071 (2) | −0.0010 (15) | −0.0008 (15) | 0.0129 (19) |
C7 | 0.0336 (15) | 0.0608 (19) | 0.0549 (19) | −0.0041 (13) | 0.0069 (13) | −0.0033 (16) |
C8 | 0.083 (3) | 0.066 (2) | 0.063 (2) | −0.0086 (19) | −0.0127 (19) | −0.0061 (19) |
C9 | 0.0267 (13) | 0.0327 (14) | 0.0627 (19) | 0.0008 (11) | 0.0059 (12) | −0.0023 (13) |
C10 | 0.0439 (17) | 0.0475 (17) | 0.068 (2) | −0.0073 (14) | 0.0141 (14) | −0.0130 (16) |
C11 | 0.0505 (19) | 0.0367 (17) | 0.101 (3) | −0.0096 (14) | 0.0177 (18) | −0.0120 (18) |
C12 | 0.0449 (18) | 0.0407 (18) | 0.104 (3) | −0.0001 (14) | 0.0002 (18) | 0.0197 (19) |
C13 | 0.059 (2) | 0.066 (2) | 0.075 (2) | −0.0091 (17) | −0.0078 (18) | 0.024 (2) |
C14 | 0.0502 (18) | 0.0480 (17) | 0.057 (2) | −0.0100 (14) | −0.0057 (14) | 0.0038 (15) |
C15 | 0.115 (4) | 0.093 (3) | 0.070 (3) | −0.040 (3) | 0.023 (2) | −0.026 (2) |
C1A | 0.0322 (13) | 0.0329 (14) | 0.0495 (17) | −0.0025 (11) | 0.0058 (12) | 0.0012 (12) |
C2A | 0.0295 (13) | 0.0316 (13) | 0.0523 (17) | −0.0036 (11) | −0.0054 (12) | 0.0030 (12) |
C3A | 0.0398 (15) | 0.0394 (15) | 0.0533 (18) | 0.0026 (12) | −0.0087 (13) | −0.0048 (13) |
C4A | 0.0580 (19) | 0.0296 (15) | 0.083 (3) | 0.0009 (14) | −0.0070 (18) | 0.0053 (16) |
C5A | 0.0499 (19) | 0.0482 (19) | 0.084 (3) | −0.0044 (15) | −0.0042 (18) | 0.0250 (18) |
C6A | 0.0377 (15) | 0.061 (2) | 0.0556 (19) | −0.0045 (14) | −0.0022 (13) | 0.0144 (16) |
C7A | 0.0358 (14) | 0.0412 (15) | 0.0533 (18) | −0.0036 (12) | −0.0014 (13) | 0.0010 (14) |
C8A | 0.071 (2) | 0.0517 (19) | 0.063 (2) | 0.0034 (16) | −0.0001 (17) | −0.0146 (17) |
C9A | 0.0253 (14) | 0.0364 (16) | 0.108 (3) | −0.0048 (12) | 0.0044 (16) | 0.0183 (18) |
C10A | 0.0394 (18) | 0.0462 (19) | 0.131 (4) | −0.0033 (15) | 0.020 (2) | 0.007 (2) |
C11A | 0.050 (2) | 0.050 (2) | 0.210 (6) | 0.0078 (19) | 0.032 (3) | 0.020 (3) |
C12A | 0.036 (2) | 0.072 (3) | 0.235 (7) | 0.009 (2) | 0.015 (3) | 0.066 (4) |
C13A | 0.050 (2) | 0.096 (3) | 0.163 (5) | −0.009 (2) | −0.015 (3) | 0.070 (4) |
C14A | 0.0370 (17) | 0.076 (2) | 0.129 (4) | −0.0114 (17) | −0.010 (2) | 0.053 (3) |
C15A | 0.100 (4) | 0.091 (3) | 0.147 (5) | −0.009 (3) | 0.028 (4) | −0.042 (3) |
S1—C1 | 1.681 (3) | C12—H12 | 0.9400 |
S1A—C1A | 1.688 (3) | C13—C14 | 1.375 (4) |
N1—C1 | 1.345 (3) | C13—H13 | 0.9400 |
N1—C2 | 1.435 (3) | C14—H14 | 0.9400 |
N1—H1 | 0.8700 | C15—H15A | 0.9700 |
N1A—C1A | 1.341 (3) | C15—H15B | 0.9700 |
N1A—C2A | 1.431 (3) | C15—H15C | 0.9700 |
N1A—H1A | 0.8700 | C2A—C7A | 1.390 (4) |
N2—C1 | 1.344 (3) | C2A—C3A | 1.394 (4) |
N2—C9 | 1.440 (3) | C3A—C4A | 1.389 (4) |
N2—H2 | 0.8700 | C3A—C8A | 1.497 (5) |
N2A—C1A | 1.342 (3) | C4A—C5A | 1.373 (5) |
N2A—C9A | 1.434 (4) | C4A—H4A | 0.9400 |
N2A—H2A | 0.8700 | C5A—C6A | 1.362 (5) |
C2—C7 | 1.374 (4) | C5A—H5A | 0.9400 |
C2—C3 | 1.386 (4) | C6A—C7A | 1.377 (4) |
C3—C4 | 1.393 (4) | C6A—H6A | 0.9400 |
C3—C8 | 1.478 (4) | C7A—H7A | 0.9400 |
C4—C5 | 1.371 (5) | C8A—H8A1 | 0.9700 |
C4—H4 | 0.9400 | C8A—H8A2 | 0.9700 |
C5—C6 | 1.378 (5) | C8A—H8A3 | 0.9700 |
C5—H5 | 0.9400 | C9A—C14A | 1.386 (5) |
C6—C7 | 1.382 (4) | C9A—C10A | 1.391 (5) |
C6—H6 | 0.9400 | C10A—C11A | 1.374 (6) |
C7—H7 | 0.9400 | C10A—C15A | 1.445 (7) |
C8—H8A | 0.9700 | C11A—C12A | 1.347 (8) |
C8—H8B | 0.9700 | C11A—H11A | 0.9400 |
C8—H8C | 0.9700 | C12A—C13A | 1.407 (8) |
C9—C10 | 1.385 (4) | C12A—H12A | 0.9400 |
C9—C14 | 1.388 (4) | C13A—C14A | 1.418 (6) |
C10—C11 | 1.403 (4) | C13A—H13A | 0.9400 |
C10—C15 | 1.506 (5) | C14A—H14A | 0.9400 |
C11—C12 | 1.359 (5) | C15A—H15D | 0.9700 |
C11—H11 | 0.9400 | C15A—H15E | 0.9700 |
C12—C13 | 1.361 (5) | C15A—H15F | 0.9700 |
C1—N1—C2 | 122.8 (2) | C10—C15—H15A | 109.5 |
C1—N1—H1 | 118.6 | C10—C15—H15B | 109.5 |
C2—N1—H1 | 118.6 | H15A—C15—H15B | 109.5 |
C1A—N1A—C2A | 127.0 (2) | C10—C15—H15C | 109.5 |
C1A—N1A—H1A | 116.5 | H15A—C15—H15C | 109.5 |
C2A—N1A—H1A | 116.5 | H15B—C15—H15C | 109.5 |
C1—N2—C9 | 125.1 (2) | N1A—C1A—N2A | 117.3 (2) |
C1—N2—H2 | 117.4 | N1A—C1A—S1A | 121.35 (19) |
C9—N2—H2 | 117.4 | N2A—C1A—S1A | 121.4 (2) |
C1A—N2A—C9A | 123.3 (2) | C7A—C2A—C3A | 120.9 (3) |
C1A—N2A—H2A | 118.3 | C7A—C2A—N1A | 119.8 (2) |
C9A—N2A—H2A | 118.3 | C3A—C2A—N1A | 119.2 (3) |
N2—C1—N1 | 116.6 (2) | C4A—C3A—C2A | 116.8 (3) |
N2—C1—S1 | 121.2 (2) | C4A—C3A—C8A | 121.6 (3) |
N1—C1—S1 | 122.2 (2) | C2A—C3A—C8A | 121.5 (3) |
C7—C2—C3 | 121.7 (3) | C5A—C4A—C3A | 122.0 (3) |
C7—C2—N1 | 119.7 (3) | C5A—C4A—H4A | 119.0 |
C3—C2—N1 | 118.6 (3) | C3A—C4A—H4A | 119.0 |
C2—C3—C4 | 117.2 (3) | C6A—C5A—C4A | 120.5 (3) |
C2—C3—C8 | 121.0 (3) | C6A—C5A—H5A | 119.8 |
C4—C3—C8 | 121.8 (3) | C4A—C5A—H5A | 119.8 |
C5—C4—C3 | 121.4 (3) | C5A—C6A—C7A | 119.4 (3) |
C5—C4—H4 | 119.3 | C5A—C6A—H6A | 120.3 |
C3—C4—H4 | 119.3 | C7A—C6A—H6A | 120.3 |
C4—C5—C6 | 120.5 (3) | C6A—C7A—C2A | 120.4 (3) |
C4—C5—H5 | 119.7 | C6A—C7A—H7A | 119.8 |
C6—C5—H5 | 119.7 | C2A—C7A—H7A | 119.8 |
C5—C6—C7 | 119.0 (3) | C3A—C8A—H8A1 | 109.5 |
C5—C6—H6 | 120.5 | C3A—C8A—H8A2 | 109.5 |
C7—C6—H6 | 120.5 | H8A1—C8A—H8A2 | 109.5 |
C2—C7—C6 | 120.2 (3) | C3A—C8A—H8A3 | 109.5 |
C2—C7—H7 | 119.9 | H8A1—C8A—H8A3 | 109.5 |
C6—C7—H7 | 119.9 | H8A2—C8A—H8A3 | 109.5 |
C3—C8—H8A | 109.5 | C14A—C9A—C10A | 123.5 (3) |
C3—C8—H8B | 109.5 | C14A—C9A—N2A | 117.9 (3) |
H8A—C8—H8B | 109.5 | C10A—C9A—N2A | 118.5 (3) |
C3—C8—H8C | 109.5 | C11A—C10A—C9A | 117.7 (5) |
H8A—C8—H8C | 109.5 | C11A—C10A—C15A | 122.0 (5) |
H8B—C8—H8C | 109.5 | C9A—C10A—C15A | 120.3 (4) |
C10—C9—C14 | 120.9 (3) | C12A—C11A—C10A | 121.8 (5) |
C10—C9—N2 | 120.3 (3) | C12A—C11A—H11A | 119.1 |
C14—C9—N2 | 118.8 (2) | C10A—C11A—H11A | 119.1 |
C9—C10—C11 | 116.9 (3) | C11A—C12A—C13A | 120.9 (4) |
C9—C10—C15 | 121.0 (3) | C11A—C12A—H12A | 119.6 |
C11—C10—C15 | 122.1 (3) | C13A—C12A—H12A | 119.6 |
C12—C11—C10 | 121.9 (3) | C12A—C13A—C14A | 119.4 (5) |
C12—C11—H11 | 119.1 | C12A—C13A—H13A | 120.3 |
C10—C11—H11 | 119.1 | C14A—C13A—H13A | 120.3 |
C11—C12—C13 | 120.4 (3) | C9A—C14A—C13A | 116.7 (5) |
C11—C12—H12 | 119.8 | C9A—C14A—H14A | 121.7 |
C13—C12—H12 | 119.8 | C13A—C14A—H14A | 121.7 |
C12—C13—C14 | 119.9 (3) | C10A—C15A—H15D | 109.5 |
C12—C13—H13 | 120.1 | C10A—C15A—H15E | 109.5 |
C14—C13—H13 | 120.1 | H15D—C15A—H15E | 109.5 |
C13—C14—C9 | 120.1 (3) | C10A—C15A—H15F | 109.5 |
C13—C14—H14 | 120.0 | H15D—C15A—H15F | 109.5 |
C9—C14—H14 | 120.0 | H15E—C15A—H15F | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1a···S1 | 0.87 | 2.50 | 3.347 (2) | 165 |
N2—H2···S1A | 0.87 | 2.49 | 3.287 (2) | 153 |
N2A—H2A···Cg(C2-C7)i | 0.87 | 2.99 | 3.588 (2) | 128 |
C12A—H12A···Cg(C9-C14)i | 0.94 | 2.97 | 3.672 (4) | 133 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C15H16N2S |
Mr | 256.37 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 223 |
a, b, c (Å) | 12.4391 (6), 9.5274 (4), 23.5683 (11) |
β (°) | 93.347 (1) |
V (Å3) | 2788.4 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.30 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Bruker AXS SMART CCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 21083, 5782, 3835 |
Rint | 0.048 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.168, 1.03 |
No. of reflections | 5782 |
No. of parameters | 329 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.83, −0.30 |
Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N1A—H1a···S1 | 0.87 | 2.50 | 3.347 (2) | 165 |
N2—H2···S1A | 0.87 | 2.49 | 3.287 (2) | 153 |
N2A—H2A···Cg(C2-C7)i | 0.87 | 2.99 | 3.588 (2) | 128 |
C12A—H12A···Cg(C9-C14)i | 0.94 | 2.97 | 3.672 (4) | 133 |
Symmetry code: (i) x+1, y, z. |
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The title compound (I) was investigated as a part of a systematic evaluation of the structural characteristics of related O-alkylthiocarbamide molecules (Ho et al., 2005; Kuan et al., 2007) and their phosphinegold(I) complexes (Ho et al., 2006; Ho & Tiekink, 2007). Two essentially identical molecules comprise the asymmetric unit of (I) with r.m.s. values of 0.017 Å and 1.05 ° for bond distances and angles, respectively (Spek, 2003). The molecules are connected into dimers via an eight-membered thioamide {···H—N—C=S}2 synthon (Fig. 1 & Table 1). Dimeric aggregates are linked into layers via N2a—H2a···Cg(C2—C7)i and C12a—H12a····Cg(C9—C14)i interactions of 2.99 and 2.97 Å, respectively (i: 1 + x, y, z). Layers stack along the c axis and are connected via hydrophobic interactions. The title molecule has been reported to function as a neutral thione ligand in the isomorphous Co and Zn dichloride structures (Prisyazhnyuk et al., 1986).