2,2′-(4-Methyl-4H-1,2,4-triazole-3,5-di­yl)dibenzene­sulfonamide

Akhtar, T.; Siddiqui, W.A.; Ashraf, A.; Tahir, M.N.

doi:10.1107/S1600536812006113

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o754

doi:10.1107/S1600536812006113

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2,2′-(4-Methyl-4H-1,2,4-triazole-3,5-diyl)dibenzenesulfonamide

Tasleem Akhtar,^a Waseeq Ahmad Siddiqui,^a Adnan Ashraf ^a and M. Nawaz Tahir ^b ^*

^aUniversity of Sargodha, Department of Chemistry, Sargodha, Pakistan, and ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 5 February 2012; accepted 11 February 2012; online 17 February 2012)

In the title compound, C₁₅H₁₅N₅O₄S₂, the dihedral angles between the central 1,2,4-triazole ring and the pendant benzene rings are 55.61 (10) and 68.59 (10)°; the dihedral angle between the benzene rings is 63.66 (9)°. Intramolecular N—H⋯N and N—H⋯O hydrogen bonds generate S(7) and S(12) rings, respectively. In the crystal, sheets extending in the (101) plane arise, with the molecules linked by C—H⋯O, N—H⋯N and N—H⋯O interactions. A C—H⋯π interaction further consolidates the structure.

Related literature

For background to benzisothiazole derivatives, see: Siddiqui et al. (2007 ); Siddiqui, Ahmad, Khan et al. (2008 ); Siddiqui, Ahmad, Siddiqui & Parvez (2008 ). For related crystal structures, see: Carlsen et al. (1995 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₅N₅O₄S₂
M_r = 393.44
Monoclinic, P 2₁ /n
a = 13.4190 (6) Å
b = 6.9043 (2) Å
c = 19.0498 (9) Å
β = 102.243 (2)°
V = 1724.80 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.34 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
15158 measured reflections
4055 independent reflections
2526 reflections with I > 2σ(I)
R_int = 0.060

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.158
S = 1.03
4055 reflections
239 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.66 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the C7/N2/C8/N3/N4 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.82 (4)	2.33 (4)	3.082 (4)	153 (3)
N1—H1B⋯N4ⁱ	0.95 (4)	1.96 (4)	2.899 (4)	171 (3)
N5—H5A⋯O4ⁱⁱ	0.94 (4)	2.10 (4)	3.011 (4)	164 (3)
N5—H5B⋯N3	0.83 (4)	2.14 (4)	2.876 (4)	148 (4)
C9—H9B⋯O2ⁱⁱⁱ	0.96	2.17	2.990 (3)	142
C14—H14⋯Cg3^iv	0.93	2.68	3.583 (4)	163
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z+1; (iii) x, y-1, z; (iv) $[-x-{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812006113/hb6629sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006113/hb6629Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006113/hb6629Isup3.cml

checkCIF report

Comment top

In continuation to our research work on the synthesis of benzisothiazole derivatives (Siddiqui, Ahmad, Khan et al., 2008; Siddiqui, Ahmad, Siddiqui & Parvez, 2008), the title compound (I), (Fig. 1) is prepared from hydrazine and commercial source of saccharin.

The crystal structures of 4-methyl-3,5-diphenyl-4H-1,2,4-triazolethe has been published which is also related to (I).

In (I), the phenyl rings A (C1–C6), B (C10—C15) and the 4-methyl-4H- 1,2,4-triazole moiety C (C7–C9/N2–N4) are planar with r. m. s. deviation of 0.0079 Å, 0.0051 Å and 0.0310 Å, respectively. The dihedral angle between A/B, A/C and B/C is 63.66 (9)°, 68.59 (1)° and 55.61 (10)°, respectively. There exist intramolecular H-bonding of N—H···N and N—H···O types (Table 1, Fig. 1) forming S (7) and S (12) ring motifs (Bernstein et al., 1995), respectively. There exist intermolecular H-bondings of C—H···.O, N—H···N and N—H···O types (Table 1, Fig. 2) which consolidates the molecules in the form two-dimensional polymeric network extending along the (101) plane. There exist C—H···π (Table 1) interactions which also play role in establishing the structure.

Related literature top

For background to benzisothiazole derivatives, see: Siddiqui et al. (2007); Siddiqui, Ahmad, Khan et al. (2008); Siddiqui, Ahmad, Siddiqui & Parvez (2008). For related crystal structures, see: Carlsen et al. (1995). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

For the synthesis of title compound, hydrazine monohydrate and saccharin were used as the starting materials following a reported procedure (Siddiqui et al., 2007). Colourless needles of (I) suitable for X-ray crystallographic study were grown from methanol at room temperature. m. p. = 483–484 K. FT—IR: (KBr, cm^-1): 3296, 3263 (NH and NH₂), 2987 (Ar. CH), 1651 (C═ N), 1541 (NH def.), 1454 (CH def.), 1315, 1151 (SO₂).

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 displacement ellipsoids drawn at the 50% probability level. The dotted lines represent the intramolecular hydrogen bonds.
	Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form two dimensional polymeric network in the plane (101).

2,2'-(4-Methyl-4H-1,2,4-triazole-3,5-diyl)dibenzenesulfonamide top

Crystal data top

C₁₅H₁₅N₅O₄S₂	F(000) = 816
M_r = 393.44	D_x = 1.515 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2526 reflections
a = 13.4190 (6) Å	θ = 2.1–27.9°
b = 6.9043 (2) Å	µ = 0.34 mm⁻¹
c = 19.0498 (9) Å	T = 296 K
β = 102.243 (2)°	Prism, colourless
V = 1724.80 (12) Å³	0.35 × 0.25 × 0.22 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Radiation source: fine-focus sealed tube	2526 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
Detector resolution: 7.60 pixels mm^-1	θ_max = 27.9°, θ_min = 2.1°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→9
T_min = 0.915, T_max = 0.938	l = −24→25
15158 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0762P)²] where P = (F_o² + 2F_c²)/3
4055 reflections	(Δ/σ)_max < 0.001
239 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.66 e Å⁻³

Crystal data top

C₁₅H₁₅N₅O₄S₂	V = 1724.80 (12) Å³
M_r = 393.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 13.4190 (6) Å	µ = 0.34 mm⁻¹
b = 6.9043 (2) Å	T = 296 K
c = 19.0498 (9) Å	0.35 × 0.25 × 0.22 mm
β = 102.243 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2526 reflections with I > 2σ(I)
T_min = 0.915, T_max = 0.938	R_int = 0.060
15158 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.158	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.63 e Å⁻³
4055 reflections	Δρ_min = −0.66 e Å⁻³
239 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	0.05268 (6)	1.38253 (11)	0.12266 (4)	0.0315 (3)
S2	−0.01231 (6)	1.09870 (12)	0.38488 (4)	0.0358 (3)
O1	−0.04824 (15)	1.3040 (3)	0.11187 (13)	0.0438 (8)
O2	0.06566 (19)	1.5630 (3)	0.08924 (13)	0.0470 (9)
O3	0.00582 (18)	1.2207 (3)	0.32800 (12)	0.0444 (8)
O4	−0.06624 (19)	1.1753 (4)	0.43601 (13)	0.0509 (9)
N1	0.0933 (2)	1.4069 (4)	0.20696 (16)	0.0362 (9)
N2	0.03107 (18)	0.9092 (3)	0.18915 (13)	0.0266 (8)
N3	0.12821 (19)	0.8730 (4)	0.29572 (14)	0.0340 (8)
N4	0.18700 (19)	0.9443 (4)	0.25015 (14)	0.0327 (8)
N5	0.0966 (2)	1.0255 (5)	0.42979 (16)	0.0423 (10)
C1	0.1333 (2)	1.2155 (4)	0.08967 (16)	0.0286 (9)
C2	0.1717 (2)	1.2741 (5)	0.03096 (17)	0.0369 (11)
C3	0.2396 (3)	1.1553 (5)	0.00495 (18)	0.0408 (11)
C4	0.2696 (3)	0.9836 (5)	0.03807 (19)	0.0447 (12)
C5	0.2307 (2)	0.9214 (5)	0.09593 (18)	0.0379 (11)
C6	0.1620 (2)	1.0357 (4)	0.12269 (16)	0.0292 (9)
C7	0.1277 (2)	0.9661 (4)	0.18635 (16)	0.0287 (9)
C8	0.0343 (2)	0.8550 (4)	0.25834 (16)	0.0286 (9)
C9	−0.05428 (11)	0.8905 (4)	0.13235 (8)	0.0214 (8)
C10	−0.05358 (11)	0.7942 (3)	0.28739 (8)	0.0307 (10)
C11	−0.08105 (11)	0.8909 (3)	0.34553 (8)	0.0330 (10)
C12	−0.16186 (11)	0.8275 (3)	0.37385 (8)	0.0438 (11)
C13	−0.2172 (3)	0.6684 (6)	0.3451 (2)	0.0513 (14)
C14	−0.1922 (3)	0.5723 (5)	0.2878 (2)	0.0480 (14)
C15	−0.1123 (3)	0.6349 (5)	0.25875 (19)	0.0400 (11)
H1A	0.063 (3)	1.330 (5)	0.2279 (18)	0.0435*
H1B	0.164 (3)	1.434 (5)	0.2203 (18)	0.0435*
H2	0.15207	1.39242	0.00900	0.0442*
H3	0.26444	1.19303	−0.03496	0.0490*
H4	0.31685	0.90708	0.02156	0.0538*
H5	0.25064	0.80228	0.11706	0.0454*
H5A	0.085 (3)	0.941 (5)	0.466 (2)	0.0509*
H5B	0.128 (3)	0.971 (6)	0.402 (2)	0.0509*
H9A	−0.11300	0.85753	0.15121	0.0321*
H9B	−0.04191	0.79024	0.10032	0.0321*
H9C	−0.06624	1.01082	0.10672	0.0321*
H12	−0.17881	0.89259	0.41243	0.0524*
H13	−0.27155	0.62553	0.36427	0.0613*
H14	−0.22961	0.46418	0.26857	0.0577*
H15	−0.09730	0.57006	0.21947	0.0480*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0307 (4)	0.0274 (4)	0.0364 (5)	0.0039 (3)	0.0074 (3)	−0.0018 (3)
S2	0.0423 (5)	0.0348 (5)	0.0332 (5)	−0.0007 (3)	0.0148 (4)	−0.0013 (3)
O1	0.0263 (11)	0.0412 (13)	0.0614 (16)	0.0034 (10)	0.0036 (11)	−0.0089 (12)
O2	0.0642 (16)	0.0277 (12)	0.0519 (16)	0.0059 (11)	0.0186 (13)	0.0070 (11)
O3	0.0603 (15)	0.0357 (13)	0.0417 (14)	0.0005 (11)	0.0209 (12)	0.0067 (11)
O4	0.0629 (16)	0.0508 (15)	0.0467 (15)	0.0013 (12)	0.0293 (12)	−0.0079 (12)
N1	0.0323 (15)	0.0407 (17)	0.0381 (17)	−0.0015 (12)	0.0128 (12)	−0.0058 (13)
N2	0.0264 (12)	0.0258 (13)	0.0283 (14)	0.0021 (10)	0.0076 (10)	−0.0016 (11)
N3	0.0288 (13)	0.0396 (16)	0.0343 (15)	0.0012 (12)	0.0084 (11)	0.0036 (12)
N4	0.0281 (13)	0.0381 (15)	0.0329 (15)	0.0027 (11)	0.0089 (11)	0.0039 (12)
N5	0.0444 (17)	0.050 (2)	0.0328 (17)	−0.0027 (15)	0.0087 (13)	−0.0014 (14)
C1	0.0262 (15)	0.0314 (17)	0.0273 (16)	0.0010 (13)	0.0038 (12)	−0.0009 (13)
C2	0.0411 (18)	0.0367 (19)	0.0317 (18)	−0.0037 (15)	0.0053 (14)	0.0017 (15)
C3	0.0415 (19)	0.051 (2)	0.0340 (19)	−0.0078 (16)	0.0171 (15)	−0.0034 (17)
C4	0.043 (2)	0.049 (2)	0.047 (2)	0.0085 (17)	0.0205 (16)	−0.0061 (18)
C5	0.0394 (18)	0.0351 (19)	0.043 (2)	0.0096 (14)	0.0170 (15)	0.0021 (15)
C6	0.0262 (15)	0.0291 (17)	0.0326 (17)	−0.0019 (13)	0.0069 (13)	−0.0053 (14)
C7	0.0262 (15)	0.0273 (16)	0.0332 (17)	0.0045 (12)	0.0080 (13)	−0.0027 (13)
C8	0.0303 (15)	0.0260 (16)	0.0302 (17)	0.0036 (12)	0.0077 (13)	−0.0024 (13)
C9	0.0180 (13)	0.0237 (15)	0.0206 (14)	−0.0009 (11)	−0.0002 (11)	−0.0030 (12)
C10	0.0279 (15)	0.0306 (17)	0.0346 (18)	0.0041 (13)	0.0092 (13)	0.0040 (14)
C11	0.0305 (16)	0.0385 (19)	0.0300 (17)	0.0013 (13)	0.0065 (13)	0.0054 (14)
C12	0.0427 (19)	0.057 (2)	0.0361 (19)	−0.0083 (17)	0.0182 (15)	0.0004 (17)
C13	0.040 (2)	0.062 (3)	0.055 (2)	−0.0150 (18)	0.0174 (18)	0.010 (2)
C14	0.040 (2)	0.043 (2)	0.060 (3)	−0.0113 (16)	0.0085 (18)	0.0022 (19)
C15	0.0381 (18)	0.0349 (19)	0.048 (2)	−0.0011 (15)	0.0111 (16)	−0.0046 (16)

Geometric parameters (Å, º) top

S1—O1	1.433 (2)	C4—C5	1.384 (5)
S1—O2	1.427 (2)	C5—C6	1.390 (4)
S1—N1	1.592 (3)	C6—C7	1.466 (4)
S1—C1	1.784 (3)	C8—C10	1.466 (3)
S2—O3	1.433 (2)	C10—C11	1.408 (2)
S2—O4	1.432 (3)	C10—C15	1.395 (4)
S2—N5	1.610 (3)	C11—C12	1.381 (2)
S2—C11	1.783 (2)	C12—C13	1.373 (4)
N2—C7	1.367 (4)	C13—C14	1.378 (5)
N2—C8	1.362 (4)	C14—C15	1.376 (6)
N2—C9	1.405 (3)	C2—H2	0.9300
N3—N4	1.382 (4)	C3—H3	0.9300
N3—C8	1.315 (4)	C4—H4	0.9300
N4—C7	1.313 (4)	C5—H5	0.9300
N1—H1B	0.95 (4)	C9—H9A	0.9600
N1—H1A	0.82 (4)	C9—H9B	0.9600
N5—H5B	0.83 (4)	C9—H9C	0.9600
N5—H5A	0.94 (4)	C12—H12	0.9300
C1—C6	1.408 (4)	C13—H13	0.9300
C1—C2	1.387 (4)	C14—H14	0.9300
C2—C3	1.393 (5)	C15—H15	0.9300
C3—C4	1.363 (5)

O1—S1—O2	117.89 (15)	N2—C8—N3	109.2 (2)
O1—S1—N1	107.21 (15)	N3—C8—C10	125.3 (3)
O1—S1—C1	109.28 (13)	N2—C8—C10	125.5 (2)
O2—S1—N1	108.05 (15)	C11—C10—C15	117.5 (2)
O2—S1—C1	105.47 (14)	C8—C10—C15	120.7 (2)
N1—S1—C1	108.68 (14)	C8—C10—C11	121.80 (19)
O3—S2—O4	119.23 (15)	C10—C11—C12	121.03 (17)
O3—S2—N5	107.80 (15)	S2—C11—C10	120.94 (13)
O3—S2—C11	108.10 (11)	S2—C11—C12	118.04 (13)
O4—S2—N5	106.69 (15)	C11—C12—C13	120.1 (2)
O4—S2—C11	106.99 (13)	C12—C13—C14	119.9 (3)
N5—S2—C11	107.53 (14)	C13—C14—C15	120.6 (3)
C7—N2—C8	106.3 (2)	C10—C15—C14	120.9 (3)
C7—N2—C9	128.4 (2)	C1—C2—H2	120.00
C8—N2—C9	125.0 (2)	C3—C2—H2	120.00
N4—N3—C8	107.6 (2)	C2—C3—H3	120.00
N3—N4—C7	107.9 (2)	C4—C3—H3	120.00
H1A—N1—H1B	125 (3)	C3—C4—H4	120.00
S1—N1—H1A	109 (2)	C5—C4—H4	119.00
S1—N1—H1B	114 (2)	C4—C5—H5	120.00
H5A—N5—H5B	112 (4)	C6—C5—H5	120.00
S2—N5—H5B	109 (3)	N2—C9—H9A	109.00
S2—N5—H5A	108 (3)	N2—C9—H9B	109.00
C2—C1—C6	120.3 (3)	N2—C9—H9C	109.00
S1—C1—C2	116.9 (2)	H9A—C9—H9B	109.00
S1—C1—C6	122.8 (2)	H9A—C9—H9C	109.00
C1—C2—C3	119.9 (3)	H9B—C9—H9C	109.00
C2—C3—C4	119.9 (3)	C11—C12—H12	120.00
C3—C4—C5	121.0 (3)	C13—C12—H12	120.00
C4—C5—C6	120.5 (3)	C12—C13—H13	120.00
C5—C6—C7	117.8 (3)	C14—C13—H13	120.00
C1—C6—C5	118.5 (3)	C13—C14—H14	120.00
C1—C6—C7	123.7 (3)	C15—C14—H14	120.00
N2—C7—N4	109.0 (3)	C10—C15—H15	120.00
N4—C7—C6	124.6 (3)	C14—C15—H15	119.00
N2—C7—C6	126.4 (3)

O1—S1—C1—C2	114.3 (2)	S1—C1—C6—C7	1.0 (4)
O1—S1—C1—C6	−68.8 (3)	C2—C1—C6—C5	1.2 (4)
O2—S1—C1—C2	−13.3 (3)	C2—C1—C6—C7	177.8 (3)
O2—S1—C1—C6	163.6 (2)	C1—C2—C3—C4	−1.2 (5)
N1—S1—C1—C2	−129.0 (2)	C2—C3—C4—C5	2.4 (6)
N1—S1—C1—C6	47.9 (3)	C3—C4—C5—C6	−1.7 (5)
O3—S2—C11—C10	43.59 (19)	C4—C5—C6—C1	−0.1 (5)
O3—S2—C11—C12	−136.53 (16)	C4—C5—C6—C7	−176.9 (3)
O4—S2—C11—C10	173.16 (17)	C1—C6—C7—N2	69.9 (4)
O4—S2—C11—C12	−6.95 (19)	C1—C6—C7—N4	−111.8 (3)
N5—S2—C11—C10	−72.55 (19)	C5—C6—C7—N2	−113.4 (3)
N5—S2—C11—C12	107.34 (18)	C5—C6—C7—N4	64.8 (4)
C8—N2—C7—N4	1.1 (3)	N2—C8—C10—C11	−121.9 (3)
C8—N2—C7—C6	179.6 (3)	N2—C8—C10—C15	59.2 (4)
C9—N2—C7—N4	−173.4 (3)	N3—C8—C10—C11	55.4 (4)
C9—N2—C7—C6	5.1 (4)	N3—C8—C10—C15	−123.6 (3)
C7—N2—C8—N3	−1.4 (3)	C8—C10—C11—S2	2.2 (3)
C7—N2—C8—C10	176.2 (2)	C8—C10—C11—C12	−177.68 (19)
C9—N2—C8—N3	173.3 (2)	C15—C10—C11—S2	−178.9 (2)
C9—N2—C8—C10	−9.2 (4)	C15—C10—C11—C12	1.3 (3)
C8—N3—N4—C7	−0.5 (3)	C8—C10—C15—C14	177.2 (3)
N4—N3—C8—N2	1.2 (3)	C11—C10—C15—C14	−1.7 (4)
N4—N3—C8—C10	−176.4 (2)	S2—C11—C12—C13	179.8 (2)
N3—N4—C7—N2	−0.4 (3)	C10—C11—C12—C13	−0.3 (3)
N3—N4—C7—C6	−178.9 (3)	C11—C12—C13—C14	−0.2 (5)
S1—C1—C2—C3	176.5 (3)	C12—C13—C14—C15	−0.3 (6)
C6—C1—C2—C3	−0.6 (5)	C13—C14—C15—C10	1.3 (6)
S1—C1—C6—C5	−175.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the C7/N2/C8/N3/N4 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.82 (4)	2.33 (4)	3.082 (4)	153 (3)
N1—H1B···N4ⁱ	0.95 (4)	1.96 (4)	2.899 (4)	171 (3)
N5—H5A···O4ⁱⁱ	0.94 (4)	2.10 (4)	3.011 (4)	164 (3)
N5—H5B···N3	0.83 (4)	2.14 (4)	2.876 (4)	148 (4)
C9—H9B···O2ⁱⁱⁱ	0.96	2.17	2.990 (3)	142
C14—H14···Cg3^iv	0.93	2.68	3.583 (4)	163

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅N₅O₄S₂
M_r	393.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	13.4190 (6), 6.9043 (2), 19.0498 (9)
β (°)	102.243 (2)
V (Å³)	1724.80 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
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	15158, 4055, 2526
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.158, 1.03
No. of reflections	4055
No. of parameters	239
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.66

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

Cg1 and Cg3 are the centroids of the C7/N2/C8/N3/N4 and C10–C15 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.82 (4)	2.33 (4)	3.082 (4)	153 (3)
N1—H1B···N4ⁱ	0.95 (4)	1.96 (4)	2.899 (4)	171 (3)
N5—H5A···O4ⁱⁱ	0.94 (4)	2.10 (4)	3.011 (4)	164 (3)
N5—H5B···N3	0.83 (4)	2.14 (4)	2.876 (4)	148 (4)
C9—H9B···O2ⁱⁱⁱ	0.96	2.17	2.990 (3)	142
C14—H14···Cg3^iv	0.93	2.68	3.583 (4)	163

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

Acknowledgements

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

References

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