1-(4-Methyl-phenyl-sulfon-yl)-5,6-di-nitro-1H-indazole.

In the title compound, C14H10N4O6S, the indazole ring system is almost perpendicular to the tosyl ring, as indicated by the dihedral angle of 89.40 (9)° between their planes. The dihedral angles between the indazole system and the nitro groups are 57.0 (3) and 31.9 (3)°. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, forming chains running along [100].

Related literature

For the biological activity of sulfonamides, see: Schmidt et al. (2008 ▶); Liu et al. (2004 ▶); Ali et al. (2008 ▶); Patel et al. (1999 ▶); Mosti et al. (2000 ▶); Bouissane et al. (2006 ▶); Abbassi et al. (2012 ▶). For the structures of similar compounds, see: Abbassi et al. (2013 ▶); Chicha et al. (2013 ▶).

Experimental

Crystal data

C14H10N4O6S

M = 362.32

Triclinic,

a = 7.4125 (3) Å

b = 8.5371 (3) Å

c = 13.0825 (5) Å

α = 90.401 (2)°

β = 95.707 (2)°

γ = 111.302 (2)°

V = 766.66 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 296 K

0.42 × 0.35 × 0.28 mm

Data collection

Bruker X8 APEX diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747

19101 measured reflections

3383 independent reflections

2984 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.125

S = 1.07

3383 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.32 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, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813034326/bt6953sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813034326/bt6953Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536813034326/bt6953Isup3.cml

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H10N4O6S	Z = 2
Mr = 362.32	F(000) = 372
Triclinic, P1	Dx = 1.570 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4125 (3) Å	Cell parameters from 3383 reflections
b = 8.5371 (3) Å	θ = 2.6–27.1°
c = 13.0825 (5) Å	µ = 0.25 mm−1
α = 90.401 (2)°	T = 296 K
β = 95.707 (2)°	Block, colourless
γ = 111.302 (2)°	0.42 × 0.35 × 0.28 mm
V = 766.66 (5) Å3

Bruker X8 APEX diffractometer	3383 independent reflections
Radiation source: fine-focus sealed tube	2984 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
φ and ω scans	θmax = 27.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.693, Tmax = 0.747	k = −10→10
19101 measured reflections	l = −16→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.0641P)2 + 0.3549P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
3383 reflections	Δρmax = 0.46 e Å−3
227 parameters	Δρmin = −0.32 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.023 (4)

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.

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
C1	0.0249 (2)	0.1414 (2)	0.35023 (12)	0.0319 (3)
C2	0.1588 (3)	0.2338 (2)	0.43202 (13)	0.0365 (4)
H2	0.2924	0.2632	0.4312	0.044*
C3	0.0814 (3)	0.2782 (2)	0.51328 (13)	0.0370 (4)
C4	−0.1209 (3)	0.2326 (2)	0.51564 (13)	0.0389 (4)
C5	−0.2510 (3)	0.1422 (2)	0.43547 (14)	0.0395 (4)
H5	−0.3845	0.1121	0.4373	0.047*
C6	−0.1768 (2)	0.0965 (2)	0.35082 (13)	0.0340 (4)
C7	−0.2599 (3)	0.0120 (2)	0.25344 (14)	0.0401 (4)
H7	−0.3929	−0.0317	0.2322	0.048*
C8	0.2592 (2)	0.2835 (2)	0.12063 (13)	0.0341 (4)
C9	0.3100 (3)	0.4449 (2)	0.16444 (15)	0.0459 (4)
H9	0.3465	0.4669	0.2347	0.055*
C10	0.3047 (3)	0.5715 (3)	0.10045 (19)	0.0540 (5)
H10	0.3356	0.6796	0.1286	0.065*
C11	0.2545 (3)	0.5414 (3)	−0.00455 (17)	0.0494 (5)
C12	0.2060 (3)	0.3792 (3)	−0.04551 (16)	0.0523 (5)
H12	0.1725	0.3578	−0.1160	0.063*
C13	0.2064 (3)	0.2490 (3)	0.01622 (14)	0.0434 (4)
H13	0.1718	0.1404	−0.0118	0.052*
C14	0.2506 (4)	0.6822 (4)	−0.0728 (2)	0.0757 (8)
H14A	0.3662	0.7798	−0.0550	0.114*
H14B	0.1380	0.7089	−0.0635	0.114*
H14C	0.2451	0.6474	−0.1434	0.114*
N1	0.2229 (3)	0.3722 (2)	0.59984 (13)	0.0499 (4)
N2	−0.1975 (3)	0.2944 (2)	0.60016 (14)	0.0537 (5)
N3	−0.1278 (2)	0.00328 (19)	0.19798 (11)	0.0396 (3)
N4	0.0489 (2)	0.07838 (19)	0.25754 (11)	0.0361 (3)
O1	0.3506 (3)	0.5014 (3)	0.58078 (16)	0.0959 (8)
O2	0.2091 (4)	0.3122 (3)	0.68252 (13)	0.0874 (7)
O3	−0.0949 (3)	0.4309 (2)	0.64245 (15)	0.0780 (6)
O4	−0.3607 (3)	0.2146 (3)	0.61839 (17)	0.0944 (7)
O5	0.4057 (2)	0.1788 (2)	0.28403 (11)	0.0491 (4)
O6	0.2305 (2)	−0.02753 (18)	0.14045 (12)	0.0538 (4)
S1	0.25624 (6)	0.11985 (6)	0.20019 (3)	0.03714 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0385 (8)	0.0306 (8)	0.0282 (8)	0.0145 (7)	0.0030 (6)	0.0020 (6)
C2	0.0380 (9)	0.0381 (9)	0.0325 (8)	0.0140 (7)	−0.0008 (7)	−0.0007 (7)
C3	0.0487 (10)	0.0311 (8)	0.0301 (8)	0.0145 (7)	0.0004 (7)	0.0002 (6)
C4	0.0540 (11)	0.0348 (9)	0.0329 (9)	0.0200 (8)	0.0128 (8)	0.0052 (7)
C5	0.0400 (9)	0.0410 (9)	0.0396 (9)	0.0160 (8)	0.0096 (7)	0.0059 (7)
C6	0.0357 (8)	0.0326 (8)	0.0337 (8)	0.0126 (7)	0.0028 (7)	0.0038 (6)
C7	0.0359 (9)	0.0423 (9)	0.0384 (9)	0.0112 (7)	−0.0012 (7)	−0.0009 (7)
C8	0.0316 (8)	0.0409 (9)	0.0322 (8)	0.0157 (7)	0.0053 (6)	−0.0024 (7)
C9	0.0515 (11)	0.0454 (10)	0.0396 (10)	0.0172 (9)	0.0019 (8)	−0.0073 (8)
C10	0.0575 (13)	0.0419 (11)	0.0643 (14)	0.0192 (9)	0.0102 (11)	0.0015 (10)
C11	0.0371 (10)	0.0604 (12)	0.0581 (12)	0.0230 (9)	0.0183 (9)	0.0208 (10)
C12	0.0515 (11)	0.0751 (14)	0.0351 (10)	0.0277 (11)	0.0092 (8)	0.0092 (9)
C13	0.0475 (10)	0.0515 (11)	0.0322 (9)	0.0193 (9)	0.0057 (8)	−0.0061 (8)
C14	0.0625 (15)	0.0889 (19)	0.094 (2)	0.0421 (14)	0.0337 (14)	0.0504 (16)
N1	0.0650 (11)	0.0446 (9)	0.0355 (9)	0.0168 (8)	−0.0028 (8)	−0.0076 (7)
N2	0.0717 (12)	0.0547 (10)	0.0418 (9)	0.0282 (9)	0.0205 (9)	0.0028 (8)
N3	0.0415 (8)	0.0407 (8)	0.0332 (8)	0.0129 (7)	−0.0027 (6)	−0.0040 (6)
N4	0.0360 (7)	0.0409 (8)	0.0298 (7)	0.0127 (6)	0.0015 (6)	−0.0040 (6)
O1	0.0898 (15)	0.0859 (14)	0.0680 (12)	−0.0171 (12)	−0.0005 (11)	−0.0216 (11)
O2	0.1383 (19)	0.0776 (12)	0.0387 (9)	0.0375 (13)	−0.0184 (10)	0.0019 (8)
O3	0.1032 (15)	0.0646 (11)	0.0696 (11)	0.0315 (10)	0.0245 (11)	−0.0176 (9)
O4	0.0930 (15)	0.0952 (15)	0.0867 (14)	0.0130 (12)	0.0569 (13)	−0.0114 (12)
O5	0.0403 (7)	0.0691 (9)	0.0438 (7)	0.0289 (7)	−0.0017 (6)	0.0018 (7)
O6	0.0701 (10)	0.0486 (8)	0.0543 (9)	0.0339 (7)	0.0137 (7)	−0.0048 (7)
S1	0.0394 (3)	0.0435 (3)	0.0349 (2)	0.0227 (2)	0.00423 (18)	−0.00191 (18)

C1—N4	1.377 (2)	C10—C11	1.384 (3)
C1—C2	1.400 (2)	C10—H10	0.9300
C1—C6	1.403 (2)	C11—C12	1.387 (3)
C2—C3	1.370 (2)	C11—C14	1.509 (3)
C2—H2	0.9300	C12—C13	1.379 (3)
C3—C4	1.409 (3)	C12—H12	0.9300
C3—N1	1.472 (2)	C13—H13	0.9300
C4—C5	1.368 (3)	C14—H14A	0.9600
C4—N2	1.469 (2)	C14—H14B	0.9600
C5—C6	1.397 (2)	C14—H14C	0.9600
C5—H5	0.9300	N1—O2	1.198 (2)
C6—C7	1.425 (2)	N1—O1	1.211 (3)
C7—N3	1.298 (2)	N2—O4	1.202 (3)
C7—H7	0.9300	N2—O3	1.227 (3)
C8—C13	1.382 (2)	N3—N4	1.383 (2)
C8—C9	1.392 (3)	N4—S1	1.6992 (15)
C8—S1	1.7429 (18)	O5—S1	1.4245 (14)
C9—C10	1.381 (3)	O6—S1	1.4186 (14)
C9—H9	0.9300
N4—C1—C2	132.03 (16)	C10—C11—C14	120.6 (2)
N4—C1—C6	105.65 (15)	C12—C11—C14	120.8 (2)
C2—C1—C6	122.32 (16)	C13—C12—C11	121.32 (19)
C3—C2—C1	116.04 (16)	C13—C12—H12	119.3
C3—C2—H2	122.0	C11—C12—H12	119.3
C1—C2—H2	122.0	C12—C13—C8	118.61 (19)
C2—C3—C4	122.37 (16)	C12—C13—H13	120.7
C2—C3—N1	115.68 (17)	C8—C13—H13	120.7
C4—C3—N1	121.92 (16)	C11—C14—H14A	109.5
C5—C4—C3	121.29 (16)	C11—C14—H14B	109.5
C5—C4—N2	117.78 (18)	H14A—C14—H14B	109.5
C3—C4—N2	120.69 (17)	C11—C14—H14C	109.5
C4—C5—C6	117.80 (17)	H14A—C14—H14C	109.5
C4—C5—H5	121.1	H14B—C14—H14C	109.5
C6—C5—H5	121.1	O2—N1—O1	124.8 (2)
C5—C6—C1	120.16 (16)	O2—N1—C3	118.03 (18)
C5—C6—C7	134.80 (17)	O1—N1—C3	117.08 (18)
C1—C6—C7	105.00 (15)	O4—N2—O3	124.3 (2)
N3—C7—C6	111.90 (16)	O4—N2—C4	118.2 (2)
N3—C7—H7	124.1	O3—N2—C4	117.26 (19)
C6—C7—H7	124.1	C7—N3—N4	106.16 (14)
C13—C8—C9	121.71 (18)	C1—N4—N3	111.21 (14)
C13—C8—S1	119.26 (14)	C1—N4—S1	128.92 (12)
C9—C8—S1	119.01 (14)	N3—N4—S1	118.15 (11)
C10—C9—C8	118.03 (18)	O6—S1—O5	121.02 (9)
C10—C9—H9	121.0	O6—S1—N4	106.26 (8)
C8—C9—H9	121.0	O5—S1—N4	103.11 (8)
C9—C10—C11	121.7 (2)	O6—S1—C8	110.38 (9)
C9—C10—H10	119.2	O5—S1—C8	110.65 (9)
C11—C10—H10	119.2	N4—S1—C8	103.62 (8)
C10—C11—C12	118.67 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O5i	0.93	2.61	3.175 (2)	120

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O5i	0.93	2.61	3.175 (2)	120

Symmetry code: (i) .