2,2'-(4-Methyl-4H-1,2,4-triazole-3,5-di-yl)dibenzene-sulfonamide.

In the title compound, C(15)H(15)N(5)O(4)S(2), 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)°. Intra-molecular 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 mol-ecules linked by C-H⋯O, N-H⋯N and N-H⋯O inter-actions. A C-H⋯π inter-action 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 = 393.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.059

wR(F 2) = 0.158

S = 1.03

4055 reflections

239 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.66 e Å−3

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006113/hb6629sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006113/hb6629Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C15H15N5O4S2	F(000) = 816
Mr = 393.44	Dx = 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

Bruker Kappa APEXII CCD diffractometer	4055 independent reflections
Radiation source: fine-focus sealed tube	2526 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.060
Detector resolution: 7.60 pixels mm-1	θmax = 27.9°, θmin = 2.1°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −5→9
Tmin = 0.915, Tmax = 0.938	l = −24→25
15158 measured reflections

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(Fo2) + (0.0762P)2] where P = (Fo2 + 2Fc2)/3
4055 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.66 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg3iv	0.93	2.68	3.583 (4)	163

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⋯Cg3iv	0.93	2.68	3.583 (4)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .