3-Acetyl-1-phenyl­thio­urea

Shahwar, D.; Tahir, M.N.; Chohan, M.M.; Ahmad, N.; Samiullah

doi:10.1107/S1600536812002371

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o508

doi:10.1107/S1600536812002371

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3-Acetyl-1-phenylthiourea

Durre Shahwar,^a M. Nawaz Tahir,^b ^* Muhammad Mansha Chohan,^a Naeem Ahmad ^a and Samiullah ^a

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 15 January 2012; accepted 19 January 2012; online 25 January 2012)

In the crystal structure of title compound, C₉H₁₀N₂OS, there are two symmetry-independent molecules, each having an intramolecular N—H⋯O hydrogen bond generating an S(6) ring motif. The benzene rings and the virtually planar acetylthoiurea fragments [r.m.s. deviations = 0.0045 and 0.0341 Å] are oriented at dihedral angles of 50.71 (6) and 62.79 (6)° in the two molecules. In the crystal, N—H⋯S and N—H⋯O hydrogen bonds link molecules via cyclic R₂²(8) and R₂²(12) motifs into a one-dimensional polymeric network extending along [101]. The intra- and intermolecular N—H⋯O interactions are part of a three-center hydrogen bond. A C—H⋯S interaction also occurs.

Related literature

For related structures, see: Othman et al. (2010 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₉H₁₀N₂OS
M_r = 194.25
Monoclinic, P 2₁ /c
a = 10.1911 (2) Å
b = 22.5480 (4) Å
c = 8.9736 (2) Å
β = 112.449 (1)°
V = 1905.77 (7) Å³
Z = 8
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 296 K
0.35 × 0.25 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.915, T_max = 0.938
16643 measured reflections
4679 independent reflections
3626 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.129
S = 1.05
4679 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.86	1.97	2.662 (2)	136
N1—H1⋯O2ⁱ	0.86	2.46	3.1967 (19)	143
N2—H2A⋯S2ⁱⁱ	0.86	2.64	3.4931 (17)	170
N3—H3A⋯O2	0.86	1.97	2.6633 (7)	137
N3—H3A⋯O1ⁱ	0.86	2.42	3.1418 (18)	142
N4—H4A⋯S1ⁱⁱ	0.86	2.57	3.4150 (18)	168
C18—H18B⋯S1ⁱⁱ	0.96	2.83	3.594 (3)	137
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812002371/gk2451sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812002371/gk2451Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812002371/gk2451Isup3.cml

checkCIF report

Comment top

The title compound I (Fig. 1) has been synthesized in search of new enzyme inhibitors.

The crystal structure of N-(3-chloropropionyl)-N'-phenylthiourea (Othman et al., 2010) has been published which is related to the title compound (I).

In (I), two molecules in the asymmetric unit are present, which differ from each other geometrically. In one molecule, the benzene ring A (C1–C6) and the acetylthoiurea moiety B (N1/C7/S1/N2/C8/O1/C9) are planar with r. m. s. deviation of 0.0045 Å and 0.0341 Å, respectively. The dihedral angle between A/B is 50.71 (6)°. In second molecule, the benzene ring C (C10–C15) and the acetylthoiurea moiety D (N3/C16/S2/N4/C17/O2/C18) are also planar with r. m. s. deviation of 0.0037 Å and 0.0453 Å, respectively and the dihedral angle between C/D is 62.79 (6)°. In both molecules, there exist classical intramolecular H–bonding of N—H···O type (Table 1, Fig. 1) with S(6) ring motif (Bernstein et al., 1995). Both molecules are interliked due to strong N—H···O, N—H···S and C—H···S types of H–bondings (Table 1, Fig. 2). The S(6) ring motifs of both molecules are connected into a four membered ring (—O···H···O···H···O—). The N—H···S type of bonding completes R₂²(8) ring motif. R₂¹(6) ring motif is formed due to C—H···S and N—H···S types of intermolecular H-bondings (Fig. 2). The molecules are linked to form of one-dimensional polymeric chains extending along [101] (Fig. 2).

Related literature top

For related structures, see: Othman et al. (2010). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

The title compound was synthesized by adding 0.1 mol (7.13 ml) of acetyl chloride dropwise to a stirred solution of KSCN (0.11 mol) in dry acetone (50 ml), followed by slow addition of aniline (0.1 mol) in dry acetone (25 ml). The mixture was refluxed for 5–10 min, then poured on ice cooled water, which resulted in crude precipitate. Recrystallization of the precipitate in from ethyl acetate yielded light green prisms (m.p. 365 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the displacement ellipsoids drawn at the 50% probability level. H atoms are shown by small circles of arbitrary radii. The dotted lines represent the intramolecular H-bondings.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form polymeric chains extending along [1 0 1] direction.

3-Acetyl-1-phenylthiourea top

Crystal data top

C₉H₁₀N₂OS	F(000) = 816
M_r = 194.25	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3626 reflections
a = 10.1911 (2) Å	θ = 2.2–28.3°
b = 22.5480 (4) Å	µ = 0.30 mm⁻¹
c = 8.9736 (2) Å	T = 296 K
β = 112.449 (1)°	Prism, light green
V = 1905.77 (7) Å³	0.35 × 0.25 × 0.22 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	4679 independent reflections
Radiation source: fine-focus sealed tube	3626 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 8.00 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→29
T_min = 0.915, T_max = 0.938	l = −11→11
16643 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0574P)² + 0.6731P] where P = (F_o² + 2F_c²)/3
4679 reflections	(Δ/σ)_max < 0.001
228 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₉H₁₀N₂OS	V = 1905.77 (7) Å³
M_r = 194.25	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.1911 (2) Å	µ = 0.30 mm⁻¹
b = 22.5480 (4) Å	T = 296 K
c = 8.9736 (2) Å	0.35 × 0.25 × 0.22 mm
β = 112.449 (1)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4679 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3626 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.938	R_int = 0.024
16643 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
4679 reflections	Δρ_min = −0.35 e Å⁻³
228 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	−0.19196 (6)	0.05015 (3)	0.17599 (8)	0.0666 (2)
O1	0.22186 (16)	−0.05280 (6)	0.3471 (2)	0.0647 (5)
N1	0.08613 (17)	0.04741 (6)	0.35398 (19)	0.0455 (5)
N2	−0.01041 (17)	−0.03499 (6)	0.19702 (19)	0.0463 (5)
C1	0.09330 (18)	0.10632 (7)	0.4158 (2)	0.0388 (5)
C2	0.1603 (2)	0.11483 (8)	0.5792 (2)	0.0455 (6)
C3	0.1800 (2)	0.17188 (9)	0.6419 (3)	0.0548 (7)
C4	0.1317 (2)	0.21994 (8)	0.5415 (3)	0.0546 (7)
C5	0.0635 (3)	0.21096 (8)	0.3790 (3)	0.0575 (7)
C6	0.0449 (2)	0.15463 (8)	0.3146 (2)	0.0532 (7)
C7	−0.0283 (2)	0.02154 (8)	0.2479 (2)	0.0428 (5)
C8	0.1098 (2)	−0.06975 (8)	0.2494 (2)	0.0449 (6)
C9	0.08992 (12)	−0.13043 (2)	0.17563 (12)	0.0596 (7)
S2	0.29361 (6)	0.11538 (2)	0.07535 (6)	0.0571 (2)
O2	0.59666 (10)	−0.02218 (2)	0.39879 (7)	0.0624 (5)
N3	0.52470 (6)	0.09140 (2)	0.33705 (7)	0.0456 (5)
N4	0.41578 (16)	0.01207 (6)	0.1764 (2)	0.0463 (5)
C10	0.5529 (2)	0.15166 (7)	0.3895 (2)	0.0419 (5)
C11	0.4580 (2)	0.18411 (10)	0.4315 (3)	0.0569 (7)
C12	0.4945 (3)	0.24100 (10)	0.4927 (3)	0.0692 (9)
C13	0.6232 (3)	0.26489 (9)	0.5078 (3)	0.0669 (8)
C14	0.7165 (3)	0.23256 (10)	0.4653 (3)	0.0641 (8)
C15	0.6826 (2)	0.17540 (9)	0.4056 (3)	0.0523 (6)
C16	0.41954 (19)	0.07247 (7)	0.2070 (2)	0.0405 (5)
C17	0.5029 (2)	−0.03202 (8)	0.2695 (2)	0.0459 (6)
C18	0.4715 (2)	−0.09258 (9)	0.1962 (3)	0.0590 (7)
H1	0.16310	0.02690	0.38876	0.0545*
H2	0.19244	0.08241	0.64760	0.0546*
H2A	−0.08394	−0.05025	0.12321	0.0555*
H3	0.22598	0.17763	0.75237	0.0658*
H4	0.14526	0.25818	0.58346	0.0655*
H5	0.02914	0.24337	0.31114	0.0690*
H6	0.00015	0.14915	0.20379	0.0639*
H9A	0.15836	−0.15710	0.24765	0.0894*
H9B	0.10276	−0.12869	0.07516	0.0894*
H9C	−0.00410	−0.14434	0.15685	0.0894*
H3A	0.58190	0.06497	0.39608	0.0548*
H4A	0.35054	0.00054	0.08761	0.0556*
H11	0.37031	0.16814	0.41908	0.0682*
H12	0.43186	0.26299	0.52351	0.0830*
H13	0.64664	0.30324	0.54715	0.0803*
H14	0.80349	0.24893	0.47639	0.0769*
H15	0.74639	0.15337	0.37671	0.0627*
H18A	0.52816	−0.09968	0.13370	0.0886*
H18B	0.37273	−0.09519	0.12774	0.0886*
H18C	0.49338	−0.12174	0.28022	0.0886*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0461 (3)	0.0524 (3)	0.0799 (4)	0.0084 (2)	0.0003 (3)	−0.0220 (3)
O1	0.0495 (8)	0.0449 (8)	0.0774 (10)	0.0053 (6)	−0.0008 (8)	−0.0177 (7)
N1	0.0430 (8)	0.0309 (8)	0.0525 (9)	0.0012 (6)	0.0071 (7)	−0.0056 (6)
N2	0.0436 (8)	0.0339 (8)	0.0500 (9)	−0.0021 (6)	0.0053 (7)	−0.0088 (6)
C1	0.0400 (9)	0.0290 (8)	0.0459 (9)	−0.0014 (7)	0.0147 (8)	−0.0031 (7)
C2	0.0501 (10)	0.0370 (9)	0.0446 (10)	0.0048 (8)	0.0128 (8)	0.0013 (7)
C3	0.0629 (12)	0.0491 (11)	0.0465 (11)	0.0021 (9)	0.0143 (9)	−0.0117 (9)
C4	0.0709 (13)	0.0340 (10)	0.0654 (13)	−0.0038 (9)	0.0332 (11)	−0.0104 (9)
C5	0.0835 (15)	0.0314 (10)	0.0602 (12)	0.0039 (9)	0.0302 (12)	0.0064 (8)
C6	0.0739 (14)	0.0386 (10)	0.0422 (10)	0.0001 (9)	0.0166 (10)	0.0025 (8)
C7	0.0470 (10)	0.0336 (9)	0.0431 (9)	−0.0001 (7)	0.0121 (8)	−0.0024 (7)
C8	0.0472 (10)	0.0342 (9)	0.0475 (10)	0.0001 (7)	0.0115 (8)	−0.0036 (7)
C9	0.0599 (12)	0.0392 (10)	0.0691 (14)	0.0009 (9)	0.0128 (11)	−0.0143 (10)
S2	0.0581 (3)	0.0369 (3)	0.0535 (3)	0.0050 (2)	−0.0041 (2)	0.0012 (2)
O2	0.0595 (9)	0.0436 (8)	0.0599 (9)	0.0107 (7)	−0.0041 (7)	−0.0056 (7)
N3	0.0441 (8)	0.0323 (7)	0.0481 (9)	0.0042 (6)	0.0037 (7)	−0.0030 (6)
N4	0.0443 (8)	0.0328 (8)	0.0485 (9)	−0.0012 (6)	0.0029 (7)	−0.0049 (6)
C10	0.0478 (10)	0.0309 (8)	0.0381 (9)	0.0018 (7)	0.0063 (8)	−0.0013 (7)
C11	0.0540 (12)	0.0503 (12)	0.0620 (13)	0.0037 (9)	0.0174 (10)	−0.0091 (9)
C12	0.0836 (17)	0.0504 (13)	0.0657 (14)	0.0180 (12)	0.0197 (13)	−0.0105 (10)
C13	0.0972 (19)	0.0329 (10)	0.0563 (13)	−0.0030 (11)	0.0134 (12)	−0.0048 (9)
C14	0.0773 (15)	0.0446 (12)	0.0647 (14)	−0.0174 (11)	0.0206 (12)	−0.0023 (10)
C15	0.0573 (12)	0.0424 (10)	0.0543 (11)	−0.0020 (9)	0.0182 (10)	−0.0015 (8)
C16	0.0394 (9)	0.0337 (9)	0.0443 (9)	−0.0012 (7)	0.0114 (8)	−0.0004 (7)
C17	0.0412 (9)	0.0357 (9)	0.0532 (11)	0.0031 (7)	0.0095 (8)	−0.0017 (8)
C18	0.0563 (12)	0.0348 (10)	0.0703 (14)	0.0060 (9)	0.0067 (10)	−0.0063 (9)

Geometric parameters (Å, º) top

S1—C7	1.671 (2)	C2—H2	0.9300
S2—C16	1.6796 (18)	C3—H3	0.9300
O1—C8	1.206 (3)	C4—H4	0.9300
O2—C17	1.2090 (19)	C5—H5	0.9300
N1—C7	1.326 (2)	C6—H6	0.9300
N1—C1	1.431 (2)	C9—H9A	0.9600
N2—C7	1.389 (2)	C9—H9B	0.9600
N2—C8	1.377 (3)	C9—H9C	0.9600
N1—H1	0.8600	C10—C15	1.382 (3)
N2—H2A	0.8600	C10—C11	1.375 (3)
N3—C10	1.4307 (17)	C11—C12	1.389 (3)
N3—C16	1.3181 (18)	C12—C13	1.376 (4)
N4—C16	1.387 (2)	C13—C14	1.363 (4)
N4—C17	1.381 (2)	C14—C15	1.388 (3)
N3—H3A	0.8600	C17—C18	1.496 (3)
N4—H4A	0.8600	C11—H11	0.9300
C1—C6	1.383 (2)	C12—H12	0.9300
C1—C2	1.374 (2)	C13—H13	0.9300
C2—C3	1.388 (3)	C14—H14	0.9300
C3—C4	1.375 (3)	C15—H15	0.9300
C4—C5	1.370 (4)	C18—H18A	0.9600
C5—C6	1.378 (3)	C18—H18B	0.9600
C8—C9	1.4996 (19)	C18—H18C	0.9600

C1—N1—C7	125.98 (17)	H9A—C9—H9C	109.00
C7—N2—C8	128.41 (16)	C8—C9—H9A	109.00
C7—N1—H1	117.00	H9B—C9—H9C	109.00
C1—N1—H1	117.00	C8—C9—H9C	109.00
C8—N2—H2A	116.00	H9A—C9—H9B	109.00
C7—N2—H2A	116.00	C8—C9—H9B	109.00
C10—N3—C16	126.30 (11)	C11—C10—C15	120.67 (17)
C16—N4—C17	128.62 (16)	N3—C10—C11	121.43 (18)
C16—N3—H3A	117.00	N3—C10—C15	117.80 (17)
C10—N3—H3A	117.00	C10—C11—C12	119.3 (2)
C17—N4—H4A	116.00	C11—C12—C13	120.1 (2)
C16—N4—H4A	116.00	C12—C13—C14	120.2 (2)
C2—C1—C6	119.87 (15)	C13—C14—C15	120.5 (3)
N1—C1—C2	118.32 (15)	C10—C15—C14	119.2 (2)
N1—C1—C6	121.61 (15)	S2—C16—N3	125.50 (11)
C1—C2—C3	119.88 (17)	S2—C16—N4	118.07 (13)
C2—C3—C4	120.3 (2)	N3—C16—N4	116.42 (14)
C3—C4—C5	119.36 (19)	O2—C17—C18	123.18 (17)
C4—C5—C6	121.01 (18)	N4—C17—C18	114.25 (16)
C1—C6—C5	119.54 (17)	O2—C17—N4	122.57 (16)
N1—C7—N2	116.73 (18)	C10—C11—H11	120.00
S1—C7—N2	117.66 (14)	C12—C11—H11	120.00
S1—C7—N1	125.58 (14)	C11—C12—H12	120.00
O1—C8—N2	122.67 (17)	C13—C12—H12	120.00
N2—C8—C9	114.58 (15)	C12—C13—H13	120.00
O1—C8—C9	122.74 (17)	C14—C13—H13	120.00
C3—C2—H2	120.00	C13—C14—H14	120.00
C1—C2—H2	120.00	C15—C14—H14	120.00
C4—C3—H3	120.00	C10—C15—H15	120.00
C2—C3—H3	120.00	C14—C15—H15	120.00
C3—C4—H4	120.00	C17—C18—H18A	109.00
C5—C4—H4	120.00	C17—C18—H18B	109.00
C6—C5—H5	120.00	C17—C18—H18C	109.00
C4—C5—H5	119.00	H18A—C18—H18B	109.00
C1—C6—H6	120.00	H18A—C18—H18C	109.00
C5—C6—H6	120.00	H18B—C18—H18C	109.00

C7—N1—C1—C2	133.6 (2)	C6—C1—C2—C3	−0.4 (3)
C7—N1—C1—C6	−51.6 (3)	N1—C1—C6—C5	−175.2 (2)
C1—N1—C7—S1	−5.7 (3)	C2—C1—C6—C5	−0.5 (3)
C1—N1—C7—N2	176.57 (16)	N1—C1—C2—C3	174.48 (19)
C8—N2—C7—S1	−173.67 (16)	C1—C2—C3—C4	0.6 (3)
C8—N2—C7—N1	4.2 (3)	C2—C3—C4—C5	0.2 (4)
C7—N2—C8—O1	−3.3 (3)	C3—C4—C5—C6	−1.2 (4)
C7—N2—C8—C9	176.44 (16)	C4—C5—C6—C1	1.3 (4)
C10—N3—C16—S2	−1.0 (2)	N3—C10—C11—C12	175.39 (18)
C16—N3—C10—C11	62.9 (2)	C15—C10—C11—C12	−0.9 (3)
C16—N3—C10—C15	−120.69 (19)	N3—C10—C15—C14	−176.23 (18)
C10—N3—C16—N4	177.67 (15)	C11—C10—C15—C14	0.2 (3)
C16—N4—C17—C18	−177.93 (19)	C10—C11—C12—C13	1.3 (4)
C17—N4—C16—S2	−176.84 (17)	C11—C12—C13—C14	−1.1 (4)
C17—N4—C16—N3	4.4 (3)	C12—C13—C14—C15	0.4 (4)
C16—N4—C17—O2	1.8 (3)	C13—C14—C15—C10	0.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.97	2.662 (2)	136
N1—H1···O2ⁱ	0.86	2.46	3.1967 (19)	143
N2—H2A···S2ⁱⁱ	0.86	2.64	3.4931 (17)	170
N3—H3A···O2	0.86	1.97	2.6633 (7)	137
N3—H3A···O1ⁱ	0.86	2.42	3.1418 (18)	142
N4—H4A···S1ⁱⁱ	0.86	2.57	3.4150 (18)	168
C18—H18B···S1ⁱⁱ	0.96	2.83	3.594 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂OS
M_r	194.25
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.1911 (2), 22.5480 (4), 8.9736 (2)
β (°)	112.449 (1)
V (Å³)	1905.77 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.35 × 0.25 × 0.22

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.915, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	16643, 4679, 3626
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.129, 1.05
No. of reflections	4679
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.97	2.662 (2)	136
N1—H1···O2ⁱ	0.86	2.46	3.1967 (19)	143
N2—H2A···S2ⁱⁱ	0.86	2.64	3.4931 (17)	170
N3—H3A···O2	0.86	1.97	2.6633 (7)	137
N3—H3A···O1ⁱ	0.86	2.42	3.1418 (18)	142
N4—H4A···S1ⁱⁱ	0.86	2.57	3.4150 (18)	168
C18—H18B···S1ⁱⁱ	0.96	2.83	3.594 (3)	137

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

Acknowledgements

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan. They also acknowledge the technical support provided by Syed Muhammad Hussain Rizvi of Bana International, Karachi, Pakistan.

References

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