Pyridine-2-carbaldehyde N4-phenethylthiosemicarbazone

Fun, H.-K.; Chantrapromma, S.; Rapheal, P.F.; Suni, V.; Prathapachandra Kurup, M.R.

doi:10.1107/S1600536805039966

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Pyridine-2-carbaldehyde N⁴-phenethylthiosemicarbazone

H.-K. Fun, S. Chantrapromma, P. F. Rapheal, V. Suni and M. R. Prathapachandra Kurup

In the molecule of the title compound, C₁₅H₁₆N₄S, the thiosemicarbazone group adopts an EE configuration, i.e. trans configurations are observed about both the azomethine and hydrazinic bonds. The phenylethyl group is disordered over two sites. In addition to an intramolecular N—H

N bond, intermolecular N—H

N hydrogen bonds [H

N = 2.063 (16) Å] link the molecules into one-dimensional chains in the a-axis direction. In the crystal structure, further stabilization is provided by weak C—H

π(arene) interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805039966/lh6546sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805039966/lh6546Isup2.hkl Contains datablock I

CCDC reference: 296723

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.032
wR factor = 0.077
Data-to-parameter ratio = 17.3

checkCIF/PLATON results

No syntax errors found





Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................      23.00 Perc.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         17

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           30.00
           From the CIF: _reflns_number_total               4232
           Count of symmetry unique reflns         2442
           Completeness (_total/calc)            173.30%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1790
           Fraction of Friedel pairs measured     0.733
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

N-Heterocyclic thiosemicarbazones are widely explored for their antimicrobial activities. For example, N(4)-substituted thiosemicarbazones are shown to possess antitumour properties in mammalian cells with the inhibition of DNA synthesis through the coordination of iron (Borges et al., 1997). 4-Morpholino-2-formylpyridine thiosemicarbazone is reported to be an active antineoplastic agent in mice bearing Sarcoma 180 ascites cells (Agarwal or Agrawal et al., 1976). Similarly, the cytotoxicity of copper and iron complexes of 5-substituted 2-formylpyridine thiosemicarbazones against Ehrlich ascites tumour cells has been measured (Antholine et al., 1976). In light of these reports, we have synthesized the title compound, (I), with the aim of investigating its antimicrobial behaviour and the related metal complexes.

The title compound is shown in Fig. 1, and selected bond lengths and angles are given in Table 1. The C15═S1 and C15—N2 bond distances are typical for these types of bonds, as are the remaining bond lengths and angles in (I) (Allen et al., 1987), and are similar to those in the structures of previously reported thiosemicarbazones (e.g. John et al., 2003; Joseph et al., 2004; Philip et al., 2004; Sreekanth et al., 2004; Usman et al., 2002). The thiosemicarbazone reveals an EE conformation since trans configurations are observed about both the C14═N3 and C15—N2 bonds.

The phenylethyl group (atoms C1–C8) is disordered over two sites with relative occupancies 0.433 (11) and 0.567 (11) for the A and B components. The pyridyl ring is coplanar with the thiosemicarbarzone group (S1/N2/N3/C14/C15), with an r.m.s. deviation of 0.025 Å and a maximum deviation of −0.173 (1) Å for atom S1. The C15—N1—C8A—C7A torsion angle of 73.6 (10)° [C15—N1—C8B—C7B = 81.3 (7)°], indicates a (+)-syn-clinal conformation in this part of the molecule. The dihedral angles between the thiosemicarbarzone group and the phenyl ring disorder components are 52.3 (2) and 50.78 (16) ° for the A and B disorder components, respectively.

In addition to an intramolecular N—H···N hydrogen-bonded S(5) ring (Bernstein et al., 1995), the molecules are linked by intramolecular N—H···N hydrogen bonds to form one-dimensional chains in the a-axis direction (Fig. 2 and Table 2). In the crystal structure, further stabilization is provided by weak C—H···π(arene) interactions (Table 2).

Experimental top

A solution containing N-methyl-N-phenyl-3- thiosemicarbazone (1 g, 5.52 m mol) (Klayman et al., 1984), 2-phenyl ethyl amine (0.725 ml, 5.52 mmol) and pyridine-2-carbaldehyde (0.525 ml, 5.52 mmol) in CH₃CN (5 ml) was heated under reflux for 1 h. The solution was chilled (overnight), and the crystals that separated were collected and washed well with CH₃CN. After recrystallization from ethanol, the sample was dried in vacuo over P₄O₁₀. Single crystals of X-ray diffraction quality were prepared by the slow evaporation of an ethanol solution of the title compound (m.p. 436–438 K).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures top

	Fig. 1. Molecular structure of (I), with ellipsoids drawn at the 60% probability level. The dashed lines denote hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed along the b axis. Hydrogen bonds are shown as dashed lines. For clarity, only one disorder component of the phenyl ethyl group is shown.

N-Benzyl-2-(2-pyridylethylene)-1-hydrazinecarbothioamide top

Crystal data top

C₁₅H₁₆N₄S	D_x = 1.305 Mg m⁻³
M_r = 284.39	Melting point = 436–438 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4238 reflections
a = 6.7341 (9) Å	θ = 1.7–30.0°
b = 8.9533 (12) Å	µ = 0.22 mm⁻¹
c = 24.003 (3) Å	T = 100 K
V = 1447.2 (3) Å³	Rod, colourless
Z = 4	0.43 × 0.19 × 0.13 mm
F(000) = 600

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	4232 independent reflections
Radiation source: fine-focus sealed tube	3928 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.7°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −12→12
T_min = 0.951, T_max = 0.972	l = −33→33
22005 measured reflections

Refinement top

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)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0358P)² + 0.2742P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4232 reflections	Δρ_max = 0.29 e Å⁻³
244 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1790 Friedels
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (6)

Crystal data top

C₁₅H₁₆N₄S	V = 1447.2 (3) Å³
M_r = 284.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.7341 (9) Å	µ = 0.22 mm⁻¹
b = 8.9533 (12) Å	T = 100 K
c = 24.003 (3) Å	0.43 × 0.19 × 0.13 mm

Data collection top

Bruker SMART APEX2 CCD area-detector diffractometer	4232 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3928 reflections with I > 2σ(I)
T_min = 0.951, T_max = 0.972	R_int = 0.041
22005 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	Δρ_max = 0.29 e Å⁻³
S = 1.04	Δρ_min = −0.19 e Å⁻³
4232 reflections	Absolute structure: Flack (1983), 1790 Friedels
244 parameters	Absolute structure parameter: 0.02 (6)
0 restraints

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	Occ. (<1)
S1	0.93075 (5)	0.37815 (4)	0.096735 (14)	0.02657 (8)
N3	0.46332 (15)	0.12067 (11)	0.08177 (4)	0.01719 (19)
N2	0.59487 (16)	0.23788 (11)	0.07685 (4)	0.0192 (2)
N1	0.78624 (16)	0.12996 (13)	0.14463 (4)	0.0205 (2)
H1A	0.7012	0.0524	0.1448	0.025*	0.433 (11)
H1B	0.6837	0.0662	0.1482	0.025*	0.567 (11)
N4	0.01498 (16)	0.03506 (11)	0.00992 (4)	0.0195 (2)
C1	0.7680 (2)	0.20527 (15)	0.26821 (5)	0.0229 (3)
C2A	0.5780 (11)	0.2982 (8)	0.2721 (4)	0.0286 (15)	0.433 (11)
H2AA	0.5619	0.3808	0.2491	0.034*	0.433 (11)
C3A	0.4311 (8)	0.2611 (8)	0.3092 (4)	0.0332 (19)	0.433 (11)
H3AA	0.3173	0.3198	0.3109	0.040*	0.433 (11)
C4A	0.4478 (10)	0.1374 (9)	0.3447 (3)	0.0330 (14)	0.433 (11)
H4AA	0.3459	0.1123	0.3691	0.040*	0.433 (11)
C5A	0.6194 (12)	0.0544 (8)	0.3422 (3)	0.0259 (12)	0.433 (11)
H5AA	0.6372	−0.0273	0.3657	0.031*	0.433 (11)
C7A	0.9213 (12)	0.2472 (8)	0.2316 (3)	0.0272 (13)	0.433 (11)
H7AA	1.0455	0.2526	0.2520	0.033*	0.433 (11)
H7AB	0.8934	0.3456	0.2166	0.033*	0.433 (11)
C8A	0.942 (2)	0.1353 (13)	0.1835 (5)	0.028 (2)	0.433 (11)
H8AA	1.0639	0.1583	0.1636	0.034*	0.433 (11)
H8AB	0.9578	0.0364	0.1994	0.034*	0.433 (11)
C2B	0.6346 (9)	0.3069 (6)	0.2570 (2)	0.0237 (8)	0.567 (11)
H2BA	0.6592	0.3786	0.2299	0.028*	0.567 (11)
C3B	0.4548 (8)	0.3073 (7)	0.2860 (2)	0.0322 (10)	0.567 (11)
H3BA	0.3587	0.3790	0.2784	0.039*	0.567 (11)
C4B	0.4216 (7)	0.1984 (8)	0.3266 (2)	0.0332 (13)	0.567 (11)
H4BA	0.3026	0.1980	0.3463	0.040*	0.567 (11)
C5B	0.5630 (9)	0.0919 (7)	0.3379 (2)	0.0294 (12)	0.567 (11)
H5BA	0.5386	0.0197	0.3649	0.035*	0.567 (11)
C7B	0.9679 (7)	0.1997 (6)	0.2330 (2)	0.0232 (8)	0.567 (11)
H7BA	1.0011	0.3008	0.2218	0.028*	0.567 (11)
H7BB	1.0735	0.1646	0.2572	0.028*	0.567 (11)
C8B	0.9645 (14)	0.1015 (9)	0.1810 (4)	0.0195 (11)	0.567 (11)
H8BA	1.0842	0.1196	0.1595	0.023*	0.567 (11)
H8BB	0.9650	−0.0026	0.1922	0.023*	0.567 (11)
C6	0.7542 (2)	0.09118 (14)	0.30723 (5)	0.0244 (3)
C9	0.16035 (18)	0.01198 (13)	0.04761 (5)	0.0166 (2)
C10	0.16384 (19)	−0.11372 (14)	0.08238 (5)	0.0196 (2)
H10A	0.2667	−0.1278	0.1077	0.024*
C11	0.0109 (2)	−0.21646 (14)	0.07821 (5)	0.0211 (2)
H11A	0.0101	−0.3010	0.1007	0.025*
C12	−0.1415 (2)	−0.19241 (15)	0.04018 (5)	0.0221 (3)
H12A	−0.2463	−0.2595	0.0370	0.027*
C13	−0.1328 (2)	−0.06508 (14)	0.00691 (5)	0.0217 (2)
H13A	−0.2344	−0.0487	−0.0186	0.026*
C14	0.31362 (17)	0.12807 (14)	0.04877 (5)	0.0171 (2)
H14A	0.3021	0.2095	0.0249	0.021*
C15	0.76441 (19)	0.24057 (13)	0.10752 (5)	0.0190 (2)
H6	0.865 (3)	0.023 (2)	0.3113 (8)	0.041 (5)*
H1N2	0.573 (3)	0.3100 (19)	0.0516 (6)	0.029 (4)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02573 (15)	0.02491 (14)	0.02908 (15)	−0.01218 (14)	0.00132 (14)	−0.00302 (13)
N3	0.0183 (5)	0.0157 (4)	0.0177 (4)	−0.0030 (4)	0.0010 (4)	−0.0001 (4)
N2	0.0186 (5)	0.0175 (5)	0.0216 (5)	−0.0041 (4)	−0.0005 (4)	0.0031 (4)
N1	0.0199 (5)	0.0261 (5)	0.0156 (4)	−0.0066 (5)	−0.0027 (4)	0.0004 (4)
N4	0.0195 (5)	0.0190 (5)	0.0199 (5)	−0.0005 (4)	−0.0026 (4)	0.0023 (4)
C1	0.0296 (7)	0.0224 (6)	0.0167 (5)	−0.0071 (5)	−0.0096 (5)	0.0005 (4)
C2A	0.024 (4)	0.0219 (19)	0.040 (4)	0.010 (2)	−0.017 (3)	−0.004 (2)
C3A	0.018 (3)	0.032 (4)	0.049 (5)	0.011 (3)	−0.015 (4)	−0.020 (3)
C4A	0.027 (2)	0.040 (3)	0.032 (3)	−0.009 (3)	0.002 (2)	−0.019 (2)
C5A	0.025 (3)	0.029 (3)	0.023 (2)	−0.001 (2)	0.001 (2)	−0.0098 (19)
C7A	0.031 (3)	0.031 (3)	0.0191 (16)	−0.014 (2)	−0.011 (2)	−0.002 (2)
C8A	0.021 (4)	0.039 (5)	0.024 (3)	−0.004 (3)	0.003 (2)	0.009 (3)
C2B	0.023 (2)	0.0240 (14)	0.0241 (19)	0.0021 (15)	−0.0043 (13)	−0.0029 (13)
C3B	0.028 (2)	0.039 (2)	0.030 (2)	0.0126 (17)	−0.0092 (18)	−0.0085 (16)
C4B	0.0226 (17)	0.054 (4)	0.023 (2)	−0.005 (3)	0.0061 (19)	−0.014 (2)
C5B	0.031 (3)	0.038 (3)	0.0194 (15)	−0.008 (2)	0.0080 (19)	−0.0046 (17)
C7B	0.0164 (16)	0.034 (2)	0.0195 (12)	−0.0035 (14)	−0.0004 (11)	−0.0008 (15)
C8B	0.0115 (17)	0.034 (3)	0.0128 (14)	0.0016 (18)	−0.0060 (12)	−0.0033 (18)
C6	0.0368 (8)	0.0195 (6)	0.0170 (5)	−0.0005 (6)	−0.0039 (5)	−0.0014 (4)
C9	0.0169 (5)	0.0169 (5)	0.0159 (5)	−0.0001 (5)	−0.0005 (4)	0.0010 (4)
C10	0.0197 (5)	0.0192 (5)	0.0198 (5)	−0.0005 (5)	−0.0022 (4)	0.0041 (4)
C11	0.0238 (6)	0.0182 (5)	0.0212 (5)	−0.0029 (5)	0.0000 (5)	0.0047 (4)
C12	0.0215 (6)	0.0210 (6)	0.0238 (6)	−0.0063 (5)	−0.0012 (5)	0.0010 (5)
C13	0.0204 (6)	0.0233 (6)	0.0214 (5)	−0.0024 (5)	−0.0049 (5)	0.0022 (5)
C14	0.0183 (5)	0.0163 (5)	0.0168 (5)	−0.0009 (5)	0.0004 (4)	0.0024 (4)
C15	0.0203 (6)	0.0203 (5)	0.0163 (5)	−0.0044 (5)	0.0010 (4)	−0.0042 (4)

Geometric parameters (Å, º) top

S1—C15	1.6849 (13)	C7A—H7AB	0.9700
N3—C14	1.2837 (15)	C8A—H8AA	0.9700
N3—N2	1.3783 (14)	C8A—H8AB	0.9700
N2—C15	1.3587 (16)	C2B—C3B	1.396 (5)
N2—H1N2	0.897 (17)	C2B—H2BA	0.9300
N1—C15	1.3401 (16)	C3B—C4B	1.396 (5)
N1—C8A	1.407 (13)	C3B—H3BA	0.9300
N1—C8B	1.506 (8)	C4B—C5B	1.374 (6)
N1—H1A	0.9000	C4B—H4BA	0.9300
N1—H1B	0.9000	C5B—C6	1.483 (6)
N4—C13	1.3416 (16)	C5B—H5BA	0.9300
N4—C9	1.3488 (16)	C7B—C8B	1.528 (9)
C1—C2B	1.306 (6)	C7B—H7BA	0.9700
C1—C6	1.3890 (17)	C7B—H7BB	0.9700
C1—C7A	1.407 (7)	C8B—H8BA	0.9700
C1—C2A	1.529 (7)	C8B—H8BB	0.9700
C1—C7B	1.590 (5)	C6—H6	0.97 (2)
C2A—C3A	1.371 (8)	C9—C10	1.4013 (16)
C2A—H2AA	0.9300	C9—C14	1.4651 (17)
C3A—C4A	1.401 (7)	C10—C11	1.3846 (17)
C3A—H3AA	0.9300	C10—H10A	0.9300
C4A—C5A	1.376 (7)	C11—C12	1.3902 (18)
C4A—H4AA	0.9300	C11—H11A	0.9300
C5A—C6	1.280 (8)	C12—C13	1.3932 (17)
C5A—H5AA	0.9300	C12—H12A	0.9300
C7A—C8A	1.535 (12)	C13—H13A	0.9300
C7A—H7AA	0.9700	C14—H14A	0.9300

C14—N3—N2	114.37 (10)	C2B—C3B—C4B	119.0 (5)
C15—N2—N3	120.47 (10)	C2B—C3B—H3BA	120.5
C15—N2—H1N2	119.3 (11)	C4B—C3B—H3BA	120.5
N3—N2—H1N2	120.1 (11)	C5B—C4B—C3B	120.7 (5)
C15—N1—C8A	119.9 (5)	C5B—C4B—H4BA	119.7
C15—N1—C8B	126.7 (4)	C3B—C4B—H4BA	119.7
C15—N1—H1A	120.2	C4B—C5B—C6	120.5 (4)
C8A—N1—H1A	120.0	C4B—C5B—H5BA	119.8
C8B—N1—H1A	112.0	C6—C5B—H5BA	119.8
C15—N1—H1B	116.6	C8B—C7B—C1	116.1 (5)
C8A—N1—H1B	122.1	C8B—C7B—H7BA	108.3
C8B—N1—H1B	116.7	C1—C7B—H7BA	108.3
C13—N4—C9	118.19 (10)	C8B—C7B—H7BB	108.3
C2B—C1—C6	127.2 (3)	C1—C7B—H7BB	108.3
C2B—C1—C7A	101.0 (3)	H7BA—C7B—H7BB	107.4
C6—C1—C7A	131.8 (4)	N1—C8B—C7B	112.8 (5)
C6—C1—C2A	107.6 (4)	N1—C8B—H8BA	109.0
C7A—C1—C2A	120.5 (3)	C7B—C8B—H8BA	109.0
C2B—C1—C7B	119.7 (2)	N1—C8B—H8BB	109.0
C6—C1—C7B	113.1 (2)	C7B—C8B—H8BB	109.0
C2A—C1—C7B	139.3 (3)	H8BA—C8B—H8BB	107.8
C3A—C2A—C1	120.8 (5)	C5A—C6—C1	132.8 (4)
C3A—C2A—H2AA	119.6	C1—C6—C5B	112.9 (3)
C1—C2A—H2AA	119.6	C5A—C6—H6	108.5 (11)
C2A—C3A—C4A	121.8 (6)	C1—C6—H6	118.7 (11)
C2A—C3A—H3AA	119.1	C5B—C6—H6	128.4 (11)
C4A—C3A—H3AA	119.1	N4—C9—C10	122.32 (11)
C5A—C4A—C3A	118.0 (6)	N4—C9—C14	114.55 (10)
C5A—C4A—H4AA	121.0	C10—C9—C14	123.13 (11)
C3A—C4A—H4AA	121.0	C11—C10—C9	118.56 (11)
C6—C5A—C4A	119.0 (6)	C11—C10—H10A	120.7
C6—C5A—H5AA	120.5	C9—C10—H10A	120.7
C4A—C5A—H5AA	120.5	C10—C11—C12	119.57 (11)
C1—C7A—C8A	111.3 (6)	C10—C11—H11A	120.2
C1—C7A—H7AA	109.4	C12—C11—H11A	120.2
C8A—C7A—H7AA	109.4	C11—C12—C13	118.19 (12)
C1—C7A—H7AB	109.4	C11—C12—H12A	120.9
C8A—C7A—H7AB	109.4	C13—C12—H12A	120.9
H7AA—C7A—H7AB	108.0	N4—C13—C12	123.15 (12)
N1—C8A—C7A	116.9 (8)	N4—C13—H13A	118.4
N1—C8A—H8AA	108.1	C12—C13—H13A	118.4
C7A—C8A—H8AA	108.1	N3—C14—C9	121.90 (11)
N1—C8A—H8AB	108.1	N3—C14—H14A	119.0
C7A—C8A—H8AB	108.1	C9—C14—H14A	119.0
H8AA—C8A—H8AB	107.3	N1—C15—N2	116.06 (11)
C1—C2B—C3B	119.7 (4)	N1—C15—S1	124.71 (10)
C1—C2B—H2BA	120.1	N2—C15—S1	119.24 (9)
C3B—C2B—H2BA	120.1

C14—N3—N2—C15	−177.02 (11)	C4A—C5A—C6—C1	0.3 (9)
C2B—C1—C2A—C3A	174.5 (18)	C4A—C5A—C6—C5B	−3.5 (10)
C6—C1—C2A—C3A	−0.7 (6)	C2B—C1—C6—C5A	−1.3 (6)
C7A—C1—C2A—C3A	−177.5 (5)	C7A—C1—C6—C5A	177.1 (6)
C7B—C1—C2A—C3A	178.0 (4)	C2A—C1—C6—C5A	0.7 (5)
C1—C2A—C3A—C4A	−0.3 (8)	C7B—C1—C6—C5A	−178.3 (5)
C2A—C3A—C4A—C5A	1.4 (9)	C2B—C1—C6—C5B	0.1 (4)
C3A—C4A—C5A—C6	−1.4 (9)	C7A—C1—C6—C5B	178.5 (4)
C2B—C1—C7A—C8A	−108.8 (6)	C2A—C1—C6—C5B	2.1 (4)
C6—C1—C7A—C8A	72.5 (7)	C7B—C1—C6—C5B	−176.9 (3)
C2A—C1—C7A—C8A	−111.5 (7)	C4B—C5B—C6—C5A	176.7 (19)
C7B—C1—C7A—C8A	59.5 (11)	C4B—C5B—C6—C1	−0.2 (5)
C15—N1—C8A—C7A	73.6 (10)	C13—N4—C9—C10	1.48 (18)
C8B—N1—C8A—C7A	−161 (5)	C13—N4—C9—C14	−178.92 (11)
C1—C7A—C8A—N1	68.3 (10)	N4—C9—C10—C11	−0.86 (18)
C6—C1—C2B—C3B	0.0 (6)	C14—C9—C10—C11	179.57 (11)
C7A—C1—C2B—C3B	−178.8 (5)	C9—C10—C11—C12	−0.28 (18)
C2A—C1—C2B—C3B	−5.8 (10)	C10—C11—C12—C13	0.73 (19)
C7B—C1—C2B—C3B	176.8 (4)	C9—N4—C13—C12	−1.00 (19)
C1—C2B—C3B—C4B	0.1 (8)	C11—C12—C13—N4	−0.1 (2)
C2B—C3B—C4B—C5B	−0.3 (8)	N2—N3—C14—C9	179.02 (10)
C3B—C4B—C5B—C6	0.3 (7)	N4—C9—C14—N3	−178.86 (11)
C2B—C1—C7B—C8B	−90.4 (5)	C10—C9—C14—N3	0.73 (18)
C6—C1—C7B—C8B	86.9 (5)	C8A—N1—C15—N2	−171.0 (6)
C7A—C1—C7B—C8B	−103.6 (12)	C8B—N1—C15—N2	175.8 (4)
C2A—C1—C7B—C8B	−91.7 (6)	C8A—N1—C15—S1	9.4 (6)
C15—N1—C8B—C7B	81.3 (7)	C8B—N1—C15—S1	−3.8 (4)
C8A—N1—C8B—C7B	19 (4)	N3—N2—C15—N1	−4.57 (16)
C1—C7B—C8B—N1	49.0 (7)	N3—N2—C15—S1	175.08 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N3	0.90	2.23	2.6481 (15)	108
N1—H1A···N3	0.90	2.29	2.6481 (15)	104
N2—H1N2···N4ⁱ	0.898 (16)	2.063 (16)	2.9597 (14)	176
C10—H10A···Cg2ⁱⁱ	0.93	2.85	3.625 (3)	142
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.87	3.6495 (15)	142

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1/2, −y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₆N₄S
M_r	284.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	6.7341 (9), 8.9533 (12), 24.003 (3)
V (Å³)	1447.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.43 × 0.19 × 0.13

Data collection
Diffractometer	Bruker SMART APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.951, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	22005, 4232, 3928
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.077, 1.04
No. of reflections	4232
No. of parameters	244
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.19
Absolute structure	Flack (1983), 1790 Friedels
Absolute structure parameter	0.02 (6)

Computer programs: APEX2 (Bruker, 2005), APEX2, SAINT (Bruker, 2005), SHELXTL (Sheldrick, 1998), SHELXTL and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

S1—C15	1.6849 (13)	N1—C8A	1.407 (13)
N3—C14	1.2837 (15)	N1—C8B	1.506 (8)
N3—N2	1.3783 (14)	N4—C13	1.3416 (16)
N2—C15	1.3587 (16)	N4—C9	1.3488 (16)
N1—C15	1.3401 (16)

C14—N3—N2	114.37 (10)	C15—N1—C8B	126.7 (4)
C15—N2—N3	120.47 (10)	N3—C14—C9	121.90 (11)
C15—N1—C8A	119.9 (5)

C2A—C1—C7A—C8A	−111.5 (7)	C15—N1—C8B—C7B	81.3 (7)
C15—N1—C8A—C7A	73.6 (10)	N3—N2—C15—S1	175.08 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···N3	0.90	2.2322	2.6481 (15)	108
N1—H1A···N3	0.90	2.2863	2.6481 (15)	104
N2—H1N2···N4ⁱ	0.898 (16)	2.063 (16)	2.9597 (14)	176
C10—H10A···Cg2ⁱⁱ	0.93	2.8467	3.625 (3)	142
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.8718	3.6495 (15)	142

Symmetry codes: (i) x+1/2, −y+1/2, −z; (ii) −x+1, y−1/2, −z+1/2; (iii) x−1/2, −y−1/2, −z.

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