N,N′-Di-o-tolyl­thio­urea

Kuan, F.S.; Tiekink, E.R.T.

doi:10.1107/S1600536807057364

N,N′-Di-o-tolylthiourea

Two independent molecules comprise the asymmetric unit in the title compound, C₁₅H₁₆N₂S. These are connected into a dimer via an eight-membered thioamide {

H—N—C=S}₂ synthon. Interactions of the type N—H

π and C—H

π consolidate molecules into a layer structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057364/hb2651sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057364/hb2651Isup2.hkl Contains datablock I

CCDC reference: 672926

checkCIF report

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

Comment top

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).

Related literature top

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).

Experimental top

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%.

Computing details top

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.

Figures top

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.

N,N'-Di-o-tolylthiourea top

Crystal data top

C₁₅H₁₆N₂S	F(000) = 1088
M_r = 256.37	D_x = 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

Data collection top

Bruker AXS SMART CCD diffractometer	3835 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 26.5°, θ_min = 1.8°
ω and ϕ scans	h = −15→15
21083 measured reflections	k = −11→11
5782 independent reflections	l = −29→28

Refinement top

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(F_o²) + (0.0792P)² + 1.2902P] where P = (F_o² + 2F_c²)/3
5782 reflections	(Δ/σ)_max < 0.001
329 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₅H₁₆N₂S	V = 2788.4 (2) Å³
M_r = 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)°

Data collection top

Bruker AXS SMART CCD diffractometer	3835 reflections with I > 2σ(I)
21083 measured reflections	R_int = 0.048
5782 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.168	H-atom parameters constrained
S = 1.03	Δρ_max = 0.83 e Å⁻³
5782 reflections	Δρ_min = −0.30 e Å⁻³
329 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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
M_r	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
R_int	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
Δρ_max, Δρ_min (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.