3-Cyclo­hexyl-1-(3,5-dinitro­benzo­yl)thio­urea

Saeed, S.; Rashid, N.; Sher, M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811013377

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1148

doi:10.1107/S1600536811013377

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3-Cyclohexyl-1-(3,5-dinitrobenzoyl)thiourea

Sohail Saeed,^a ‡ Naghmana Rashid,^a Muhammad Sher,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, Research Complex, Allama Iqbal Open University, Islamabad 44000, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 6 April 2011; accepted 9 April 2011; online 16 April 2011)

The structure of the title thiourea derivative, C₁₄H₁₆N₄O₅S, features an almost planar central C₂N₂OS fragment (r.m.s. deviation = 0.005 Å), an arrangement stabilized by an intramolecular N—H⋯O hydrogen bond. The terminal rings are twisted out of this plane, the dihedral angle formed with the benzene ring being 33.22 (10)°. The cyclohexyl ring is disordered, with two orientations (50:50) being resolved. The mean plane passing through the atoms of each disordered component forms dihedral angles of 65.7 (2) and 82.4 (3)° with the central plane. Centrosymmetric dimers mediated by an eight-membered {⋯HNC=S}₂ synthon occur in the crystal.

Related literature

For the biological activity of thiourea derivatives, see: Venkatachalam et al. (2004 ); Saeed et al. (2011 ). For related thiourea structures, see: Gunasekaran et al. (2010 ); Saeed et al. (2010 ); Dzulkifli et al. (2011 ).

Experimental

Crystal data

C₁₄H₁₆N₄O₅S
M_r = 352.37
Monoclinic, P 2₁ /c
a = 12.3404 (7) Å
b = 9.0506 (5) Å
c = 14.6534 (6) Å
β = 90.385 (5)°
V = 1636.57 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 295 K
0.20 × 0.15 × 0.10 mm

Data collection

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.955, T_max = 0.977
7954 measured reflections
3649 independent reflections
1948 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.211
S = 1.01
3649 reflections
271 parameters
25 restraints
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1	0.88	1.89	2.639 (4)	142
N1—H1′⋯O1	0.88	1.99	2.639 (4)	130
N2—H2⋯S1ⁱ	0.88	2.65	3.449 (3)	152
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013377/hb5839sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013377/hb5839Isup2.hkl

checkCIF report

Comment top

Continuing structural studies (Gunasekaran et al. 2010; Saeed et al. 2010; Dzulkifli et al., 2011) of thiourea derivatives are motivated by their biological potential (Venkatachalam et al., 2004; Saeed et al., 2011) and led to the investigation of the title compound, (I).

The molecular structure of (I), Fig. 1, is highly twisted with dihedral angles formed between the central chromophore (r.m.s. = 0.0054 Å for C7,C8,N1,N2,O1 & S1) and the benzene ring being 33.22 (10) °. Two orientations of equal weight were found for the cyclohexyl ring, each with a chair conformation, and these make angles of 65.74 (24) and 82.42 (30) °, respectively, with the central plane. The N—H atoms are anti as are the S and O atoms. As a consequence, the N1—H atom forms an intramolecular hydrogen bond with the carbonyl-O1 atom to close a pseudo six-membered ring, Table 1; there are two values cited owing to the disorder in the molecule. The nitro groups are effectively co-planar with the benzene ring to which they are bonded as seen in the values of the O2—N3—C11—C10 and O4—N4—C13—C12 torsion angles of 1.2 (5) and -7.0 (5) °, respectively.

The most prominent feature of the crystal packing is the formation of centrosymmetric eight-membered {···HNC═S}₂ synthon leading to dimeric aggregates, Fig. 2 and Table 1.

Related literature top

For the biological activity of thiourea derivatives, see: Venkatachalam et al. (2004); Saeed et al. (2011). For related thiourea structures, see: Gunasekaran et al. (2010); Saeed et al. (2010); Dzulkifli et al. (2011).

Experimental top

A solution of 3,5-dinitrobenzoyl chloride (0.01 mol) in anhydrous acetone (75 ml) and 3% tetrabutylammonium bromide (TBAB), as a phase-transfer catalyst (PTC), in anhydrous acetone was added drop-wise to a suspension of dry potassium thiocyanate (0.01 mol) in acetone (50 ml). The reaction mixture was refluxed for 50 min. After cooling to room temperature, a solution of cyclohexylamine (0.01 mol) in anhydrous acetone (25 ml) was added drop-wise and the resulting mixture refluxed for 3 h. Hydrochloric acid (0.1 N, 300 ml) was added and the solution was filtered. The solid product was washed with water and purified by re-crystallization from ethanol; Yield: 1.50 g (88%) and M.pt. 409 K. IR (KBr, cm^-1): 3215 ν(NH), 1673 (C=O), 1527 (benzene ring), 1138 ν(C═S). Anal. Calcd. for C₁₄H₁₆N₄O₅S: C, 47.72; H, 4.58; N, 15.90; S, 9.10%. Found: C, 47.51; H, 4.75; N, 15.88; S, 9.11%.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 35% probability level. Only one orientation of the disordered cyclohexyl ring is shown.
	Fig. 2. Supramolecular dimer in (I) mediated by N—H···S hydrogen bonding shown as orange dashed lines. Only one orientation of the disordered cyclohexyl ring is shown.

3-Cyclohexyl-1-(3,5-dinitrobenzoyl)thiourea top

Crystal data top

C₁₄H₁₆N₄O₅S	F(000) = 736
M_r = 352.37	D_x = 1.430 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2522 reflections
a = 12.3404 (7) Å	θ = 2.6–29.2°
b = 9.0506 (5) Å	µ = 0.23 mm⁻¹
c = 14.6534 (6) Å	T = 295 K
β = 90.385 (5)°	Prism, colorless
V = 1636.57 (15) Å³	0.20 × 0.15 × 0.10 mm
Z = 4

Data collection top

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector	3649 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	1948 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.024
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ω scans	h = −11→16
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→9
T_min = 0.955, T_max = 0.977	l = −19→18
7954 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0901P)² + 0.5204P] where P = (F_o² + 2F_c²)/3
3649 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 0.22 e Å⁻³
25 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₄H₁₆N₄O₅S	V = 1636.57 (15) Å³
M_r = 352.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.3404 (7) Å	µ = 0.23 mm⁻¹
b = 9.0506 (5) Å	T = 295 K
c = 14.6534 (6) Å	0.20 × 0.15 × 0.10 mm
β = 90.385 (5)°

Data collection top

Agilent Technologies SuperNova Dual diffractometer with an Atlas detector	3649 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	1948 reflections with I > 2σ(I)
T_min = 0.955, T_max = 0.977	R_int = 0.024
7954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	25 restraints
wR(F²) = 0.211	H-atom parameters constrained
S = 1.01	Δρ_max = 0.22 e Å⁻³
3649 reflections	Δρ_min = −0.28 e Å⁻³
271 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
S1	0.41365 (9)	0.64167 (12)	0.59283 (6)	0.0914 (4)
O1	0.2058 (2)	0.5972 (4)	0.33847 (18)	0.1069 (9)
O2	0.1940 (3)	0.2554 (4)	0.0798 (2)	0.1410 (13)
O3	0.3315 (3)	0.2306 (4)	−0.0052 (3)	0.1351 (13)
O4	0.6723 (3)	0.4548 (4)	0.0872 (2)	0.1237 (11)
O5	0.6733 (2)	0.6067 (4)	0.2004 (2)	0.1140 (10)
N1	0.2226 (2)	0.6699 (3)	0.5124 (2)	0.0864 (9)
H1	0.1881	0.6629	0.4598	0.104*	0.50
H1'	0.1777	0.6614	0.4657	0.104*	0.50
N2	0.3606 (2)	0.5812 (3)	0.42290 (16)	0.0689 (7)
H2	0.4294	0.5564	0.4197	0.083*
N3	0.2883 (4)	0.2769 (4)	0.0621 (3)	0.0964 (10)
N4	0.6288 (3)	0.5175 (4)	0.1510 (2)	0.0907 (9)
C1	0.1543 (7)	0.7215 (9)	0.5861 (6)	0.074 (3)	0.50
H1A	0.1990	0.7735	0.6313	0.088*	0.50
C2	0.0991 (8)	0.5900 (9)	0.6317 (6)	0.084 (3)	0.50
H2A	0.1529	0.5203	0.6537	0.101*	0.50
H2B	0.0520	0.5398	0.5885	0.101*	0.50
C3	0.0323 (6)	0.6513 (8)	0.7122 (4)	0.094 (2)	0.50
H3A	−0.0055	0.5709	0.7420	0.113*	0.50
H3B	0.0807	0.6964	0.7567	0.113*	0.50
C4	−0.0488 (6)	0.7647 (9)	0.6791 (5)	0.106 (3)	0.50
H4A	−0.1009	0.7171	0.6389	0.127*	0.50
H4B	−0.0879	0.8040	0.7309	0.127*	0.50
C5	0.0049 (6)	0.8899 (8)	0.6289 (5)	0.098 (3)	0.50
H5A	0.0532	0.9427	0.6700	0.117*	0.50
H5B	−0.0496	0.9586	0.6069	0.117*	0.50
C6	0.0701 (8)	0.8278 (11)	0.5471 (5)	0.091 (3)	0.50
H6A	0.0222	0.7764	0.5051	0.109*	0.50
H6B	0.1054	0.9075	0.5146	0.109*	0.50
C1'	0.1883 (7)	0.7287 (12)	0.6020 (6)	0.121 (6)	0.50
H1B	0.2530	0.7692	0.6321	0.145*	0.50
C2'	0.1393 (7)	0.6133 (12)	0.6672 (7)	0.101 (4)	0.50
H2C	0.1891	0.5312	0.6747	0.121*	0.50
H2D	0.1277	0.6576	0.7267	0.121*	0.50
C3'	0.0326 (8)	0.5580 (10)	0.6290 (9)	0.149 (6)	0.50
H3C	0.0025	0.4846	0.6699	0.179*	0.50
H3D	0.0448	0.5112	0.5704	0.179*	0.50
C4'	−0.0484 (6)	0.6857 (12)	0.6172 (9)	0.146 (5)	0.50
H4C	−0.0635	0.7300	0.6760	0.175*	0.50
H4D	−0.1159	0.6487	0.5917	0.175*	0.50
C5'	0.0006 (8)	0.8018 (12)	0.5529 (10)	0.150 (5)	0.50
H5C	0.0107	0.7586	0.4930	0.180*	0.50
H5D	−0.0492	0.8842	0.5467	0.180*	0.50
C6'	0.1077 (7)	0.8568 (10)	0.5890 (8)	0.106 (3)	0.50
H6C	0.0968	0.9063	0.6469	0.127*	0.50
H6D	0.1376	0.9281	0.5466	0.127*	0.50
C7	0.3244 (3)	0.6318 (3)	0.5079 (2)	0.0695 (8)
C8	0.3013 (3)	0.5664 (4)	0.3450 (2)	0.0755 (9)
C9	0.3604 (3)	0.5071 (4)	0.2637 (2)	0.0701 (8)
C10	0.3015 (3)	0.4227 (4)	0.2026 (2)	0.0757 (9)
H10	0.2288	0.4025	0.2131	0.091*
C11	0.3514 (3)	0.3689 (3)	0.1262 (2)	0.0753 (9)
C12	0.4585 (3)	0.3965 (3)	0.1073 (2)	0.0751 (9)
H12	0.4916	0.3582	0.0556	0.090*
C13	0.5142 (3)	0.4833 (3)	0.1684 (2)	0.0700 (8)
C14	0.4681 (3)	0.5400 (3)	0.2462 (2)	0.0691 (8)
H14	0.5082	0.5988	0.2860	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0966 (7)	0.1080 (8)	0.0695 (5)	0.0228 (6)	0.0037 (5)	−0.0177 (5)
O1	0.0737 (17)	0.145 (3)	0.1016 (18)	0.0229 (17)	−0.0108 (14)	−0.0007 (17)
O2	0.127 (3)	0.161 (3)	0.135 (3)	−0.052 (3)	−0.019 (2)	−0.027 (2)
O3	0.144 (3)	0.126 (3)	0.136 (3)	−0.003 (2)	−0.014 (2)	−0.066 (2)
O4	0.117 (2)	0.121 (2)	0.134 (2)	−0.0209 (19)	0.045 (2)	−0.043 (2)
O5	0.108 (2)	0.131 (2)	0.1037 (19)	−0.0431 (19)	0.0195 (17)	−0.0334 (18)
N1	0.0751 (18)	0.095 (2)	0.0897 (19)	0.0212 (16)	0.0215 (15)	0.0104 (16)
N2	0.0680 (15)	0.0767 (16)	0.0620 (14)	0.0098 (13)	0.0057 (12)	0.0030 (12)
N3	0.111 (3)	0.080 (2)	0.098 (2)	−0.012 (2)	−0.019 (2)	−0.0087 (18)
N4	0.102 (2)	0.086 (2)	0.0843 (19)	−0.0157 (19)	0.0192 (18)	−0.0099 (17)
C1	0.058 (5)	0.071 (6)	0.093 (5)	0.015 (4)	0.026 (4)	0.001 (4)
C2	0.097 (8)	0.077 (5)	0.078 (6)	0.007 (6)	0.011 (6)	−0.005 (5)
C3	0.115 (6)	0.100 (5)	0.069 (4)	−0.024 (5)	0.029 (4)	−0.017 (4)
C4	0.085 (5)	0.131 (8)	0.103 (6)	−0.007 (5)	0.020 (5)	−0.071 (6)
C5	0.085 (5)	0.095 (6)	0.114 (6)	0.018 (4)	0.022 (5)	−0.037 (5)
C6	0.070 (6)	0.099 (7)	0.103 (7)	0.023 (6)	−0.007 (5)	−0.006 (5)
C1'	0.088 (8)	0.119 (11)	0.157 (11)	0.041 (7)	0.051 (7)	0.032 (8)
C2'	0.087 (7)	0.128 (8)	0.087 (7)	−0.004 (6)	0.009 (5)	0.007 (6)
C3'	0.106 (8)	0.160 (12)	0.180 (12)	−0.038 (8)	−0.043 (8)	0.069 (10)
C4'	0.071 (5)	0.162 (10)	0.203 (13)	−0.001 (7)	−0.014 (7)	0.077 (10)
C5'	0.099 (8)	0.124 (9)	0.227 (15)	−0.010 (8)	−0.057 (9)	0.049 (10)
C6'	0.090 (7)	0.092 (7)	0.136 (9)	0.007 (5)	−0.004 (6)	0.000 (6)
C7	0.076 (2)	0.0639 (18)	0.0689 (18)	0.0095 (16)	0.0127 (16)	0.0061 (14)
C8	0.077 (2)	0.076 (2)	0.073 (2)	0.0066 (18)	−0.0027 (17)	0.0090 (16)
C9	0.083 (2)	0.0665 (18)	0.0607 (16)	0.0028 (17)	−0.0076 (15)	0.0113 (15)
C10	0.078 (2)	0.0711 (19)	0.077 (2)	−0.0019 (17)	−0.0112 (17)	0.0110 (17)
C11	0.096 (3)	0.0574 (18)	0.0726 (19)	−0.0027 (18)	−0.0183 (18)	0.0045 (15)
C12	0.102 (3)	0.0593 (18)	0.0641 (18)	0.0011 (18)	−0.0014 (18)	0.0019 (15)
C13	0.083 (2)	0.0607 (17)	0.0665 (18)	−0.0054 (16)	−0.0008 (16)	0.0053 (15)
C14	0.084 (2)	0.0631 (18)	0.0598 (16)	−0.0052 (16)	−0.0035 (16)	0.0051 (14)

Geometric parameters (Å, º) top

S1—C7	1.659 (4)	C5—H5B	0.9700
O1—C8	1.215 (4)	C6—H6A	0.9700
O2—N3	1.210 (5)	C6—H6B	0.9700
O3—N3	1.200 (4)	C1'—C6'	1.539 (8)
O4—N4	1.221 (4)	C1'—C2'	1.542 (8)
O5—N4	1.213 (4)	C1'—H1B	0.9800
N1—C7	1.305 (4)	C2'—C3'	1.512 (8)
N1—C1	1.452 (6)	C2'—H2C	0.9700
N1—C1'	1.481 (8)	C2'—H2D	0.9700
N1—H1	0.8800	C3'—C4'	1.537 (9)
N1—H1'	0.8800	C3'—H3C	0.9700
N2—C8	1.358 (4)	C3'—H3D	0.9700
N2—C7	1.402 (4)	C4'—C5'	1.537 (8)
N2—H2	0.8800	C4'—H4C	0.9700
N3—C11	1.474 (5)	C4'—H4D	0.9700
N4—C13	1.471 (5)	C5'—C6'	1.505 (8)
C1—C6	1.524 (8)	C5'—H5C	0.9700
C1—C2	1.527 (8)	C5'—H5D	0.9700
C1—H1A	0.9800	C6'—H6C	0.9700
C2—C3	1.547 (7)	C6'—H6D	0.9700
C2—H2A	0.9700	C8—C9	1.501 (5)
C2—H2B	0.9700	C9—C10	1.380 (5)
C3—C4	1.511 (8)	C9—C14	1.388 (4)
C3—H3A	0.9700	C10—C11	1.370 (5)
C3—H3B	0.9700	C10—H10	0.9300
C4—C5	1.507 (7)	C11—C12	1.375 (5)
C4—H4A	0.9700	C12—C13	1.372 (5)
C4—H4B	0.9700	C12—H12	0.9300
C5—C6	1.552 (8)	C13—C14	1.376 (4)
C5—H5A	0.9700	C14—H14	0.9300

C7—N1—C1	133.3 (5)	C2'—C1'—H1B	107.3
C7—N1—C1'	114.9 (5)	C3'—C2'—C1'	109.8 (7)
C7—N1—H1	113.3	C3'—C2'—H2C	109.7
C1—N1—H1	113.3	C1'—C2'—H2C	109.7
C7—N1—H1'	122.6	C3'—C2'—H2D	109.7
C1'—N1—H1'	122.6	C1'—C2'—H2D	109.7
C8—N2—C7	127.2 (3)	H2C—C2'—H2D	108.2
C8—N2—H2	116.4	C2'—C3'—C4'	110.9 (7)
C7—N2—H2	116.4	C2'—C3'—H3C	109.5
O3—N3—O2	123.5 (4)	C4'—C3'—H3C	109.5
O3—N3—C11	119.1 (4)	C2'—C3'—H3D	109.5
O2—N3—C11	117.4 (4)	C4'—C3'—H3D	109.5
O5—N4—O4	124.5 (3)	H3C—C3'—H3D	108.1
O5—N4—C13	117.9 (3)	C3'—C4'—C5'	109.0 (7)
O4—N4—C13	117.6 (3)	C3'—C4'—H4C	109.9
N1—C1—C6	108.7 (6)	C5'—C4'—H4C	109.9
N1—C1—C2	109.8 (6)	C3'—C4'—H4D	109.9
C6—C1—C2	110.6 (7)	C5'—C4'—H4D	109.9
N1—C1—H1A	109.3	H4C—C4'—H4D	108.3
C6—C1—H1A	109.3	C6'—C5'—C4'	111.1 (7)
C2—C1—H1A	109.3	C6'—C5'—H5C	109.4
C1—C2—C3	107.2 (5)	C4'—C5'—H5C	109.4
C1—C2—H2A	110.3	C6'—C5'—H5D	109.4
C3—C2—H2A	110.3	C4'—C5'—H5D	109.4
C1—C2—H2B	110.3	H5C—C5'—H5D	108.0
C3—C2—H2B	110.3	C5'—C6'—C1'	111.1 (7)
H2A—C2—H2B	108.5	C5'—C6'—H6C	109.4
C4—C3—C2	110.7 (5)	C1'—C6'—H6C	109.4
C4—C3—H3A	109.5	C5'—C6'—H6D	109.4
C2—C3—H3A	109.5	C1'—C6'—H6D	109.4
C4—C3—H3B	109.5	H6C—C6'—H6D	108.0
C2—C3—H3B	109.5	N1—C7—N2	116.4 (3)
H3A—C3—H3B	108.1	N1—C7—S1	125.6 (3)
C5—C4—C3	112.0 (6)	N2—C7—S1	118.0 (2)
C5—C4—H4A	109.2	O1—C8—N2	124.1 (3)
C3—C4—H4A	109.2	O1—C8—C9	119.7 (3)
C5—C4—H4B	109.2	N2—C8—C9	116.2 (3)
C3—C4—H4B	109.2	C10—C9—C14	120.0 (3)
H4A—C4—H4B	107.9	C10—C9—C8	117.2 (3)
C4—C5—C6	109.7 (6)	C14—C9—C8	122.8 (3)
C4—C5—H5A	109.7	C11—C10—C9	119.2 (3)
C6—C5—H5A	109.7	C11—C10—H10	120.4
C4—C5—H5B	109.7	C9—C10—H10	120.4
C6—C5—H5B	109.7	C10—C11—C12	122.6 (3)
H5A—C5—H5B	108.2	C10—C11—N3	118.8 (4)
C1—C6—C5	107.1 (5)	C12—C11—N3	118.6 (3)
C1—C6—H6A	110.3	C13—C12—C11	116.7 (3)
C5—C6—H6A	110.3	C13—C12—H12	121.6
C1—C6—H6B	110.3	C11—C12—H12	121.6
C5—C6—H6B	110.3	C12—C13—C14	123.1 (3)
H6A—C6—H6B	108.5	C12—C13—N4	119.0 (3)
N1—C1'—C6'	110.4 (8)	C14—C13—N4	117.9 (3)
N1—C1'—C2'	115.0 (8)	C13—C14—C9	118.3 (3)
C6'—C1'—C2'	109.4 (6)	C13—C14—H14	120.8
N1—C1'—H1B	107.3	C9—C14—H14	120.8
C6'—C1'—H1B	107.3

C7—N1—C1—C6	147.6 (6)	C8—N2—C7—N1	−0.6 (5)
C1'—N1—C1—C6	134 (2)	C8—N2—C7—S1	−179.3 (3)
C7—N1—C1—C2	−91.4 (9)	C7—N2—C8—O1	0.6 (6)
C1'—N1—C1—C2	−105 (2)	C7—N2—C8—C9	−179.1 (3)
N1—C1—C2—C3	177.3 (7)	O1—C8—C9—C10	−31.7 (5)
C6—C1—C2—C3	−62.8 (10)	N2—C8—C9—C10	148.0 (3)
C1—C2—C3—C4	57.7 (10)	O1—C8—C9—C14	145.0 (4)
C2—C3—C4—C5	−56.9 (9)	N2—C8—C9—C14	−35.3 (4)
C3—C4—C5—C6	57.5 (9)	C14—C9—C10—C11	1.7 (5)
N1—C1—C6—C5	−175.5 (8)	C8—C9—C10—C11	178.6 (3)
C2—C1—C6—C5	63.9 (10)	C9—C10—C11—C12	−0.5 (5)
C4—C5—C6—C1	−59.6 (10)	C9—C10—C11—N3	179.1 (3)
C7—N1—C1'—C6'	141.7 (5)	O3—N3—C11—C10	179.4 (4)
C1—N1—C1'—C6'	−49.4 (18)	O2—N3—C11—C10	1.2 (5)
C7—N1—C1'—C2'	−94.0 (7)	O3—N3—C11—C12	−1.1 (5)
C1—N1—C1'—C2'	74.9 (19)	O2—N3—C11—C12	−179.3 (4)
N1—C1'—C2'—C3'	−66.7 (10)	C10—C11—C12—C13	−0.8 (5)
C6'—C1'—C2'—C3'	58.1 (11)	N3—C11—C12—C13	179.6 (3)
C1'—C2'—C3'—C4'	−59.8 (12)	C11—C12—C13—C14	0.9 (5)
C2'—C3'—C4'—C5'	58.6 (13)	C11—C12—C13—N4	−179.4 (3)
C3'—C4'—C5'—C6'	−57.3 (14)	O5—N4—C13—C12	172.3 (3)
C4'—C5'—C6'—C1'	57.8 (13)	O4—N4—C13—C12	−7.0 (5)
N1—C1'—C6'—C5'	69.9 (10)	O5—N4—C13—C14	−8.0 (5)
C2'—C1'—C6'—C5'	−57.5 (11)	O4—N4—C13—C14	172.6 (3)
C1—N1—C7—N2	177.5 (5)	C12—C13—C14—C9	0.3 (5)
C1'—N1—C7—N2	−177.5 (5)	N4—C13—C14—C9	−179.4 (3)
C1—N1—C7—S1	−3.8 (7)	C10—C9—C14—C13	−1.6 (5)
C1'—N1—C7—S1	1.1 (6)	C8—C9—C14—C13	−178.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.89	2.639 (4)	142
N1—H1′···O1	0.88	1.99	2.639 (4)	130
N2—H2···S1ⁱ	0.88	2.65	3.449 (3)	152

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₆N₄O₅S
M_r	352.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	12.3404 (7), 9.0506 (5), 14.6534 (6)
β (°)	90.385 (5)
V (Å³)	1636.57 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Agilent Technologies SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.955, 0.977
No. of measured, independent and observed [I > 2σ(I)] reflections	7954, 3649, 1948
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.211, 1.01
No. of reflections	3649
No. of parameters	271
No. of restraints	25
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.28

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.88	1.89	2.639 (4)	142
N1—H1'···O1	0.88	1.99	2.639 (4)	130
N2—H2···S1ⁱ	0.88	2.65	3.449 (3)	152

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: sohail262001@yahoo.com.

Acknowledgements

The authors are grateful to Allama Iqbal Open University, Islamabad, Pakistan, for the allocation of research and analytical laboratory facilities. The authors also thank the University of Malaya for supporting this study.

References

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