Crystal structure of N-carbamo­thioyl-2-methyl­benzamide

Adam, F.; Ameram, N.; Tan, W.M.

doi:10.1107/S2056989015009585

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 6| June 2015| Page o425

doi:10.1107/S2056989015009585

Open

access

Crystal structure of N-carbamothioyl-2-methylbenzamide

Farook Adam,^a ^* Nadiah Ameram ^a and Wai Mun Tan ^a

^aSchool of Chemical Sciences, Universiti Sains Malaysia, 11800 Georgetown, Penang, Malaysia
^*Correspondence e-mail: farookdr@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 May 2015; accepted 19 May 2015; online 28 May 2015)

There are two molecules in the asymmetric unit of the title compound, C₉H₁₀N₂OS. In one, the dihedral angle between the aromatic ring and the carbamothioyl group is 52.31 (7)° and in the other it is 36.16 (6)°. Each molecule features an intramolecular N—H⋯O hydrogen bond, which generates an S(6) ring and the O and S atoms have an anti disposition. In the crystal, molecules are linked by N—H⋯S and N—H⋯O hydrogen bonds, generating separate [130] and [1-30] infinite chains. Weak C—H⋯O and C—H⋯S interactions are also observed.

Keywords: crystal structure; benzamide; thiourea; hydrogen bonding.

CCDC reference: 1401733

1. Related literature

For related structures, see: Saeed & Flörke (2007 ); Shoukat et al. (2007 ); Hassan et al. (2008a ,b ,c ); Ameram et al. (2015 ).

2. Experimental

2.1. Crystal data

C₉H₁₀N₂OS
M_r = 194.25
Monoclinic, C 2/c
a = 22.7886 (12) Å
b = 7.1133 (3) Å
c = 25.5388 (13) Å
β = 113.664 (3)°
V = 3791.8 (3) Å³
Z = 16
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 100 K
0.46 × 0.33 × 0.10 mm

2.2. Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.814, T_max = 0.872
70711 measured reflections
5697 independent reflections
4862 reflections with I > 2σ(I)
R_int = 0.051

2.3. Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.110
S = 1.10
5697 reflections
261 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯S1Aⁱ	0.80 (2)	2.60 (2)	3.3227 (16)	151.2 (18)
N1B—H1B⋯S1Bⁱⁱ	0.84 (2)	2.65 (2)	3.4780 (14)	172 (2)
N2A—H2A⋯S1Bⁱⁱⁱ	0.85 (2)	2.49 (2)	3.2945 (15)	157.8 (19)
N2B—H2B⋯O1B	0.83 (2)	1.98 (2)	2.6404 (18)	136 (2)
N2A—H3A⋯O1A	0.83 (2)	2.02 (2)	2.6515 (19)	133 (2)
N2B—H3B⋯S1Aⁱⁱⁱ	0.89 (2)	2.49 (2)	3.3800 (14)	177 (2)
C5B—H5BA⋯O1A^iv	0.95	2.45	3.3584 (19)	160
C9B—H9BA⋯S1Aⁱ	0.98	2.80	3.6946 (17)	152
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) -x+1, -y+1, -z; (iii) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iv) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1401733

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S2056989015009585/hb7426sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015009585/hb7426Isup2.hkl

Supporting information file. DOI: 10.1107/S2056989015009585/hb7426Isup3.cml

checkCIF report

Introduction top

In the crystal, molecules are linked by pairs of C=O—H hydrogen bonds with the methyl group from molecule (B) is facing the group from the molecule (A) forming slabs which is parallel to the benzene ring plane (A) as the bond of C6–C7 (A and B) can free to rotate.

Experimental top

The title compound (Fig. 1) is a benzoyl thiourea intermediate to a compound recently reported by us (Ameram et al., 2015) and there is no substituent at the end of thioamide group.

Synthesis and crystallization top

Freshly prepared substituted o-benzoyl chloride (13 mmol) was added dropwise to a stirred acetone solution (30 ml) of ammonium thiocyanate (13 mmol). The mixture was stirred for 10 min. A white side product which is ammonium chloride was filtered off. The compound was left at room temperature to crystallize, to yield colourless plates of the title compound.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The H-atoms on the N atoms were located in a difference-Fourier map and were freely refined. All other H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.96 Å and U_iso(H) = 1.2U_eq(aromatic C) or 1.5U_eq(methyl C).

Results and discussion top

Related literature top

For related structures, see: Saeed & Flörke (2007); Shoukat et al. (2007); Hassan et al. (2008a,b,c); Ameram et al. (2015).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing the atom labellling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

N-Carbamothioyl-2-methylbenzamide top

Crystal data top

C₉H₁₀N₂OS	F(000) = 1632
M_r = 194.25	D_x = 1.361 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 22.7886 (12) Å	Cell parameters from 9948 reflections
b = 7.1133 (3) Å	θ = 3.0–29.9°
c = 25.5388 (13) Å	µ = 0.30 mm⁻¹
β = 113.664 (3)°	T = 100 K
V = 3791.8 (3) Å³	Plate, colourless
Z = 16	0.46 × 0.33 × 0.10 mm

Data collection top

Bruker APEX DUO CCD diffractometer	5697 independent reflections
Radiation source: fine-focus sealed tube	4862 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ϕ and ω scans	θ_max = 30.4°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −32→32
T_min = 0.814, T_max = 0.872	k = −10→10
70711 measured reflections	l = −36→36

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0488P)² + 4.2106P] where P = (F_o² + 2F_c²)/3
S = 1.10	(Δ/σ)_max = 0.001
5697 reflections	Δρ_max = 0.45 e Å⁻³
261 parameters	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₉H₁₀N₂OS	V = 3791.8 (3) Å³
M_r = 194.25	Z = 16
Monoclinic, C2/c	Mo Kα radiation
a = 22.7886 (12) Å	µ = 0.30 mm⁻¹
b = 7.1133 (3) Å	T = 100 K
c = 25.5388 (13) Å	0.46 × 0.33 × 0.10 mm
β = 113.664 (3)°

Data collection top

Bruker APEX DUO CCD diffractometer	5697 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4862 reflections with I > 2σ(I)
T_min = 0.814, T_max = 0.872	R_int = 0.051
70711 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.45 e Å⁻³
5697 reflections	Δρ_min = −0.22 e Å⁻³
261 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S1A	0.20453 (2)	0.37036 (5)	0.04623 (2)	0.02123 (9)
O1A	0.05447 (5)	0.09550 (16)	−0.11126 (5)	0.0285 (3)
N1A	0.15344 (6)	0.12795 (17)	−0.03834 (5)	0.0195 (2)
N2A	0.08336 (6)	0.3410 (2)	−0.02644 (7)	0.0264 (3)
C1A	0.12721 (8)	−0.1174 (2)	−0.16760 (7)	0.0255 (3)
C2A	0.14877 (8)	−0.2742 (2)	−0.18702 (7)	0.0290 (3)
H2AA	0.1428	−0.2801	−0.2260	0.035*
C3A	0.17880 (7)	−0.4224 (2)	−0.15103 (7)	0.0257 (3)
H3AA	0.1925	−0.5289	−0.1656	0.031*
C4A	0.18880 (7)	−0.4154 (2)	−0.09401 (7)	0.0239 (3)
H4AA	0.2096	−0.5165	−0.0692	0.029*
C5A	0.16820 (7)	−0.2595 (2)	−0.07329 (6)	0.0215 (3)
H5AA	0.1756	−0.2531	−0.0340	0.026*
C6A	0.13688 (7)	−0.11301 (19)	−0.10979 (6)	0.0190 (3)
C7A	0.11026 (7)	0.0452 (2)	−0.08773 (6)	0.0202 (3)
C8A	0.14215 (7)	0.27880 (19)	−0.00939 (6)	0.0186 (3)
C9A	0.09650 (12)	0.0421 (3)	−0.20800 (9)	0.0462 (5)
H9AA	0.1169	0.1608	−0.1906	0.069*
H9AB	0.0507	0.0472	−0.2159	0.069*
H9AC	0.1019	0.0222	−0.2438	0.069*
S1B	0.45007 (2)	0.73146 (5)	−0.00298 (2)	0.02408 (10)
O1B	0.31413 (5)	0.45230 (16)	−0.16642 (5)	0.0258 (2)
N1B	0.40643 (6)	0.47799 (17)	−0.08568 (5)	0.0187 (2)
N2B	0.33660 (6)	0.71847 (19)	−0.08869 (6)	0.0227 (3)
C1B	0.35431 (7)	0.0654 (2)	−0.17791 (6)	0.0199 (3)
C2B	0.38290 (8)	−0.0911 (2)	−0.19102 (6)	0.0240 (3)
H2BA	0.3574	−0.1983	−0.2076	0.029*
C3B	0.44736 (8)	−0.0943 (2)	−0.18057 (7)	0.0278 (3)
H3BA	0.4653	−0.2025	−0.1903	0.033*
C4B	0.48592 (7)	0.0595 (2)	−0.15600 (7)	0.0276 (3)
H4BA	0.5300	0.0586	−0.1496	0.033*
C5B	0.45933 (7)	0.2151 (2)	−0.14083 (6)	0.0231 (3)
H5BA	0.4856	0.3203	−0.1234	0.028*
C6B	0.39425 (7)	0.2184 (2)	−0.15102 (6)	0.0184 (3)
C7B	0.36692 (7)	0.3907 (2)	−0.13618 (6)	0.0190 (3)
C8B	0.39349 (6)	0.64135 (19)	−0.06277 (6)	0.0177 (3)
C9B	0.28310 (7)	0.0629 (2)	−0.19377 (7)	0.0244 (3)
H9BA	0.2741	0.1143	−0.1622	0.037*
H9BB	0.2674	−0.0667	−0.2014	0.037*
H9BC	0.2615	0.1396	−0.2281	0.037*
H1B	0.4428 (11)	0.433 (3)	−0.0664 (9)	0.038 (6)*
H3A	0.0543 (11)	0.291 (3)	−0.0542 (10)	0.039 (6)*
H1A	0.1904 (10)	0.102 (3)	−0.0300 (8)	0.028 (5)*
H3B	0.3275 (10)	0.827 (3)	−0.0763 (9)	0.037 (6)*
H2B	0.3111 (11)	0.667 (3)	−0.1184 (10)	0.039 (6)*
H2A	0.0765 (10)	0.437 (3)	−0.0096 (9)	0.038 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.02084 (16)	0.02238 (18)	0.01948 (17)	0.00473 (13)	0.00704 (13)	−0.00419 (13)
O1A	0.0193 (5)	0.0211 (5)	0.0368 (6)	0.0039 (4)	0.0025 (4)	−0.0060 (5)
N1A	0.0165 (5)	0.0181 (6)	0.0231 (6)	0.0031 (4)	0.0070 (5)	−0.0040 (5)
N2A	0.0192 (6)	0.0210 (6)	0.0374 (8)	0.0021 (5)	0.0098 (6)	−0.0096 (6)
C1A	0.0309 (8)	0.0211 (7)	0.0227 (7)	−0.0002 (6)	0.0089 (6)	0.0015 (6)
C2A	0.0364 (8)	0.0294 (8)	0.0220 (7)	0.0000 (7)	0.0127 (6)	−0.0030 (6)
C3A	0.0257 (7)	0.0225 (7)	0.0313 (8)	−0.0003 (6)	0.0140 (6)	−0.0073 (6)
C4A	0.0245 (7)	0.0184 (7)	0.0281 (8)	0.0049 (5)	0.0100 (6)	0.0013 (6)
C5A	0.0232 (7)	0.0197 (7)	0.0211 (7)	0.0037 (5)	0.0085 (5)	0.0004 (5)
C6A	0.0187 (6)	0.0152 (6)	0.0213 (7)	−0.0007 (5)	0.0062 (5)	−0.0021 (5)
C7A	0.0203 (6)	0.0143 (6)	0.0242 (7)	−0.0003 (5)	0.0070 (5)	−0.0004 (5)
C8A	0.0198 (6)	0.0153 (6)	0.0225 (7)	0.0004 (5)	0.0104 (5)	−0.0004 (5)
C9A	0.0681 (14)	0.0369 (10)	0.0309 (9)	0.0167 (10)	0.0169 (9)	0.0128 (8)
S1B	0.01921 (17)	0.02226 (18)	0.02552 (19)	0.00457 (13)	0.00349 (14)	−0.00916 (14)
O1B	0.0238 (5)	0.0242 (5)	0.0222 (5)	0.0056 (4)	0.0017 (4)	−0.0022 (4)
N1B	0.0178 (5)	0.0167 (5)	0.0182 (6)	0.0029 (4)	0.0035 (4)	−0.0036 (4)
N2B	0.0201 (6)	0.0209 (6)	0.0231 (6)	0.0052 (5)	0.0044 (5)	−0.0038 (5)
C1B	0.0230 (6)	0.0196 (7)	0.0142 (6)	−0.0007 (5)	0.0045 (5)	−0.0002 (5)
C2B	0.0297 (7)	0.0183 (7)	0.0200 (7)	−0.0002 (6)	0.0059 (6)	−0.0032 (5)
C3B	0.0304 (8)	0.0240 (7)	0.0248 (7)	0.0073 (6)	0.0068 (6)	−0.0060 (6)
C4B	0.0220 (7)	0.0303 (8)	0.0277 (8)	0.0038 (6)	0.0069 (6)	−0.0079 (6)
C5B	0.0223 (7)	0.0227 (7)	0.0216 (7)	−0.0004 (5)	0.0059 (5)	−0.0056 (6)
C6B	0.0215 (6)	0.0174 (6)	0.0147 (6)	0.0015 (5)	0.0056 (5)	−0.0012 (5)
C7B	0.0207 (6)	0.0171 (6)	0.0179 (6)	−0.0005 (5)	0.0063 (5)	−0.0020 (5)
C8B	0.0188 (6)	0.0155 (6)	0.0195 (6)	0.0015 (5)	0.0083 (5)	−0.0003 (5)
C9B	0.0227 (7)	0.0265 (8)	0.0216 (7)	−0.0043 (6)	0.0063 (6)	−0.0044 (6)

Geometric parameters (Å, º) top

S1A—C8A	1.6858 (15)	S1B—C8B	1.6806 (14)
O1A—C7A	1.2215 (17)	O1B—C7B	1.2207 (17)
N1A—C7A	1.3818 (19)	N1B—C8B	1.3850 (18)
N1A—C8A	1.3845 (18)	N1B—C7B	1.3883 (18)
N1A—H1A	0.80 (2)	N1B—H1B	0.84 (2)
N2A—C8A	1.3083 (18)	N2B—C8B	1.3156 (18)
N2A—H3A	0.83 (2)	N2B—H3B	0.89 (2)
N2A—H2A	0.86 (2)	N2B—H2B	0.83 (2)
C1A—C2A	1.388 (2)	C1B—C2B	1.397 (2)
C1A—C6A	1.403 (2)	C1B—C6B	1.408 (2)
C1A—C9A	1.504 (2)	C1B—C9B	1.507 (2)
C2A—C3A	1.385 (2)	C2B—C3B	1.384 (2)
C2A—H2AA	0.9500	C2B—H2BA	0.9500
C3A—C4A	1.381 (2)	C3B—C4B	1.386 (2)
C3A—H3AA	0.9500	C3B—H3BA	0.9500
C4A—C5A	1.389 (2)	C4B—C5B	1.390 (2)
C4A—H4AA	0.9500	C4B—H4BA	0.9500
C5A—C6A	1.389 (2)	C5B—C6B	1.399 (2)
C5A—H5AA	0.9500	C5B—H5BA	0.9500
C6A—C7A	1.492 (2)	C6B—C7B	1.4909 (19)
C9A—H9AA	0.9800	C9B—H9BA	0.9800
C9A—H9AB	0.9800	C9B—H9BB	0.9800
C9A—H9AC	0.9800	C9B—H9BC	0.9800

C7A—N1A—C8A	126.92 (12)	C8B—N1B—C7B	126.81 (12)
C7A—N1A—H1A	115.6 (14)	C8B—N1B—H1B	113.6 (15)
C8A—N1A—H1A	115.7 (14)	C7B—N1B—H1B	119.6 (15)
C8A—N2A—H3A	119.9 (16)	C8B—N2B—H3B	120.3 (14)
C8A—N2A—H2A	118.2 (14)	C8B—N2B—H2B	117.4 (16)
H3A—N2A—H2A	122 (2)	H3B—N2B—H2B	122 (2)
C2A—C1A—C6A	117.74 (14)	C2B—C1B—C6B	117.41 (13)
C2A—C1A—C9A	119.66 (15)	C2B—C1B—C9B	118.81 (13)
C6A—C1A—C9A	122.58 (15)	C6B—C1B—C9B	123.77 (13)
C3A—C2A—C1A	121.71 (15)	C3B—C2B—C1B	121.89 (14)
C3A—C2A—H2AA	119.1	C3B—C2B—H2BA	119.1
C1A—C2A—H2AA	119.1	C1B—C2B—H2BA	119.1
C4A—C3A—C2A	120.05 (14)	C2B—C3B—C4B	120.35 (14)
C4A—C3A—H3AA	120.0	C2B—C3B—H3BA	119.8
C2A—C3A—H3AA	120.0	C4B—C3B—H3BA	119.8
C3A—C4A—C5A	119.48 (14)	C3B—C4B—C5B	119.14 (14)
C3A—C4A—H4AA	120.3	C3B—C4B—H4BA	120.4
C5A—C4A—H4AA	120.3	C5B—C4B—H4BA	120.4
C4A—C5A—C6A	120.29 (14)	C4B—C5B—C6B	120.64 (14)
C4A—C5A—H5AA	119.9	C4B—C5B—H5BA	119.7
C6A—C5A—H5AA	119.9	C6B—C5B—H5BA	119.7
C5A—C6A—C1A	120.71 (13)	C5B—C6B—C1B	120.48 (13)
C5A—C6A—C7A	119.33 (13)	C5B—C6B—C7B	119.09 (13)
C1A—C6A—C7A	119.88 (13)	C1B—C6B—C7B	120.34 (13)
O1A—C7A—N1A	122.93 (13)	O1B—C7B—N1B	122.28 (13)
O1A—C7A—C6A	122.40 (13)	O1B—C7B—C6B	122.72 (13)
N1A—C7A—C6A	114.67 (12)	N1B—C7B—C6B	115.00 (12)
N2A—C8A—N1A	117.98 (13)	N2B—C8B—N1B	118.11 (13)
N2A—C8A—S1A	123.67 (12)	N2B—C8B—S1B	122.68 (11)
N1A—C8A—S1A	118.34 (10)	N1B—C8B—S1B	119.21 (10)
C1A—C9A—H9AA	109.5	C1B—C9B—H9BA	109.5
C1A—C9A—H9AB	109.5	C1B—C9B—H9BB	109.5
H9AA—C9A—H9AB	109.5	H9BA—C9B—H9BB	109.5
C1A—C9A—H9AC	109.5	C1B—C9B—H9BC	109.5
H9AA—C9A—H9AC	109.5	H9BA—C9B—H9BC	109.5
H9AB—C9A—H9AC	109.5	H9BB—C9B—H9BC	109.5

C6A—C1A—C2A—C3A	0.1 (2)	C6B—C1B—C2B—C3B	−2.8 (2)
C9A—C1A—C2A—C3A	178.34 (18)	C9B—C1B—C2B—C3B	176.38 (14)
C1A—C2A—C3A—C4A	−0.9 (3)	C1B—C2B—C3B—C4B	0.5 (2)
C2A—C3A—C4A—C5A	0.4 (2)	C2B—C3B—C4B—C5B	1.4 (3)
C3A—C4A—C5A—C6A	1.0 (2)	C3B—C4B—C5B—C6B	−1.0 (2)
C4A—C5A—C6A—C1A	−1.9 (2)	C4B—C5B—C6B—C1B	−1.3 (2)
C4A—C5A—C6A—C7A	174.80 (13)	C4B—C5B—C6B—C7B	−177.71 (14)
C2A—C1A—C6A—C5A	1.3 (2)	C2B—C1B—C6B—C5B	3.2 (2)
C9A—C1A—C6A—C5A	−176.90 (17)	C9B—C1B—C6B—C5B	−175.98 (14)
C2A—C1A—C6A—C7A	−175.35 (14)	C2B—C1B—C6B—C7B	179.53 (13)
C9A—C1A—C6A—C7A	6.5 (2)	C9B—C1B—C6B—C7B	0.4 (2)
C8A—N1A—C7A—O1A	−2.2 (2)	C8B—N1B—C7B—O1B	−0.6 (2)
C8A—N1A—C7A—C6A	178.65 (13)	C8B—N1B—C7B—C6B	178.45 (13)
C5A—C6A—C7A—O1A	−126.72 (16)	C5B—C6B—C7B—O1B	139.95 (15)
C1A—C6A—C7A—O1A	50.0 (2)	C1B—C6B—C7B—O1B	−36.5 (2)
C5A—C6A—C7A—N1A	52.41 (18)	C5B—C6B—C7B—N1B	−39.13 (19)
C1A—C6A—C7A—N1A	−130.91 (15)	C1B—C6B—C7B—N1B	144.47 (13)
C7A—N1A—C8A—N2A	7.1 (2)	C7B—N1B—C8B—N2B	4.7 (2)
C7A—N1A—C8A—S1A	−173.59 (12)	C7B—N1B—C8B—S1B	−176.08 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S1Aⁱ	0.80 (2)	2.60 (2)	3.3227 (16)	151.2 (18)
N1B—H1B···S1Bⁱⁱ	0.84 (2)	2.65 (2)	3.4780 (14)	172 (2)
N2A—H2A···S1Bⁱⁱⁱ	0.85 (2)	2.49 (2)	3.2945 (15)	157.8 (19)
N2B—H2B···O1B	0.83 (2)	1.98 (2)	2.6404 (18)	136 (2)
N2A—H3A···O1A	0.83 (2)	2.02 (2)	2.6515 (19)	133 (2)
N2B—H3B···S1Aⁱⁱⁱ	0.89 (2)	2.49 (2)	3.3800 (14)	177 (2)
C5B—H5BA···O1A^iv	0.95	2.45	3.3584 (19)	160
C9B—H9BA···S1Aⁱ	0.98	2.80	3.6946 (17)	152

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1, −y+1, −z; (iii) −x+1/2, −y+3/2, −z; (iv) x+1/2, y+1/2, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S1Aⁱ	0.80 (2)	2.60 (2)	3.3227 (16)	151.2 (18)
N1B—H1B···S1Bⁱⁱ	0.84 (2)	2.65 (2)	3.4780 (14)	172 (2)
N2A—H2A···S1Bⁱⁱⁱ	0.85 (2)	2.49 (2)	3.2945 (15)	157.8 (19)
N2B—H2B···O1B	0.83 (2)	1.98 (2)	2.6404 (18)	136 (2)
N2A—H3A···O1A	0.83 (2)	2.02 (2)	2.6515 (19)	133 (2)
N2B—H3B···S1Aⁱⁱⁱ	0.89 (2)	2.49 (2)	3.3800 (14)	177 (2)
C5B—H5BA···O1A^iv	0.95	2.45	3.3584 (19)	160
C9B—H9BA···S1Aⁱ	0.98	2.80	3.6946 (17)	152

Symmetry codes: (i) −x+1/2, −y+1/2, −z; (ii) −x+1, −y+1, −z; (iii) −x+1/2, −y+3/2, −z; (iv) x+1/2, y+1/2, z.

Acknowledgements

The authors thank Universiti Sains Malaysia for research grants Nos. PKIMIA846017 and RU-1001/PKIMIA/811269 which partially supported this work.

References

Ameram, N., Adam, F., Fatihah, N. N. & Al-Juaid, S. (2015). Acta Cryst. E71, o356. CSD CrossRef IUCr Journals Google Scholar
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008a). Acta Cryst. E64, o1727. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008b). Acta Cryst. E64, o2083. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hassan, I. N., Yamin, B. M. & Kassim, M. B. (2008c). Acta Cryst. E64, o2167. Web of Science CSD CrossRef IUCr Journals Google Scholar
Saeed, A. & Flörke, U. (2007). Acta Cryst. E63, o4259. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Shoukat, N., Rauf, M. K., Bolte, M. & Badshah, A. (2007). Acta Cryst. E63, o3207. Web of Science CSD CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 71| Part 6| June 2015| Page o425

doi:10.1107/S2056989015009585

Open

access