3,5-Dimethyl-1-(4-nitro-phen-yl)-1H-pyrazole.

In the title pyrazole derivative, C(11)H(11)N(3)O(2), the benzene ring is twisted [dihedral angle = 31.38 (12)°] with respect to the pyrazole ring (r.m.s. deviation = 0.009 Å). The nitro group is effectively coplanar with the benzene ring to which it is attached [O-N-C-C torsion angle = -6.5 (3)°]. Supra-molecular chains along the b axis are formed owing to π-π inter-actions [3.8653 (2) Å] between translationally related mol-ecules involving both the five- and six-membered rings.

Related literature

For the therapeutic importance of pyrazole compounds, see: Sil et al. (2005 ▶); Haddad et al. (2004 ▶). For the diverse pharmacological activities of pyrazole compounds, see: Bekhit et al. (2010 ▶, 2012) ▶; Higashi et al. (2006 ▶). For the synthesis, see: Butler & James (1982 ▶); Claramunt et al. (2006 ▶). For recently reported structures, see: Wardell et al. (2012 ▶); Baddeley et al. (2012 ▶).

Experimental

Crystal data

C11H11N3O2

M = 217.23

Orthorhombic,

a = 21.3909 (13) Å

b = 3.8653 (2) Å

c = 12.4514 (8) Å

V = 1029.51 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 120 K

0.26 × 0.19 × 0.04 mm

Data collection

Rigaku Saturn724+ diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.598, T max = 1.000

6055 measured reflections

1202 independent reflections

1148 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.101

S = 1.09

1202 reflections

147 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009579/hg5187sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009579/hg5187Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009579/hg5187Isup3.cml

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

C11H11N3O2	F(000) = 456
Mr = 217.23	Dx = 1.402 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 6528 reflections
a = 21.3909 (13) Å	θ = 2.9–27.5°
b = 3.8653 (2) Å	µ = 0.10 mm−1
c = 12.4514 (8) Å	T = 120 K
V = 1029.51 (11) Å3	Plate, light-yellow
Z = 4	0.26 × 0.19 × 0.04 mm

Rigaku Saturn724+ diffractometer	1202 independent reflections
Radiation source: Rotating Anode	1148 reflections with I > 2σ(I)
Confocal monochromator	Rint = 0.046
Detector resolution: 28.5714 pixels mm-1	θmax = 27.5°, θmin = 3.3°
profile data from ω–scans	h = −27→25
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −4→5
Tmin = 0.598, Tmax = 1.000	l = −16→10
6055 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0563P)2 + 0.2711P] where P = (Fo2 + 2Fc2)/3
1202 reflections	(Δ/σ)max < 0.001
147 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.20 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.25661 (11)	0.8154 (7)	0.1996 (2)	0.0529 (6)
O2	0.19518 (9)	0.7062 (6)	0.0666 (2)	0.0479 (6)
N1	0.44986 (9)	0.1859 (5)	−0.12778 (15)	0.0229 (4)
N2	0.50113 (9)	0.0689 (5)	−0.07183 (17)	0.0246 (4)
N3	0.24680 (11)	0.7002 (5)	0.1097 (2)	0.0348 (5)
C1	0.45879 (11)	0.1711 (6)	−0.23678 (19)	0.0246 (5)
C2	0.54135 (11)	−0.0271 (6)	−0.14708 (19)	0.0260 (5)
C3	0.51697 (11)	0.0328 (6)	−0.2510 (2)	0.0274 (5)
H3	0.5371	−0.0138	−0.3175	0.033*
C4	0.60413 (11)	−0.1723 (7)	−0.1187 (2)	0.0308 (5)
H4A	0.6188	−0.0674	−0.0517	0.046*
H4B	0.6339	−0.1211	−0.1765	0.046*
H4C	0.6008	−0.4234	−0.1095	0.046*
C5	0.41435 (12)	0.3090 (7)	−0.3190 (2)	0.0313 (5)
H5A	0.3823	0.1346	−0.3344	0.047*
H5B	0.4372	0.3637	−0.3850	0.047*
H5C	0.3943	0.5191	−0.2914	0.047*
C6	0.39825 (10)	0.3116 (6)	−0.06913 (18)	0.0225 (5)
C7	0.40877 (11)	0.4650 (6)	0.03071 (18)	0.0251 (5)
H7	0.4502	0.4872	0.0574	0.030*
C8	0.35886 (11)	0.5849 (6)	0.0909 (2)	0.0267 (5)
H8	0.3654	0.6858	0.1595	0.032*
C9	0.29891 (11)	0.5547 (6)	0.0488 (2)	0.0274 (5)
C10	0.28776 (11)	0.4044 (6)	−0.0498 (2)	0.0282 (5)
H10	0.2463	0.3888	−0.0769	0.034*
C11	0.33738 (11)	0.2765 (6)	−0.1088 (2)	0.0259 (5)
H11	0.3302	0.1657	−0.1758	0.031*

	U11	U22	U33	U12	U13	U23
O1	0.0478 (12)	0.0660 (13)	0.0448 (13)	0.0087 (12)	0.0146 (10)	−0.0132 (11)
O2	0.0249 (9)	0.0550 (13)	0.0640 (14)	0.0063 (9)	0.0092 (9)	0.0016 (11)
N1	0.0223 (9)	0.0249 (9)	0.0216 (9)	−0.0003 (7)	−0.0012 (7)	0.0011 (7)
N2	0.0227 (8)	0.0262 (10)	0.0249 (9)	0.0020 (7)	−0.0012 (7)	0.0005 (9)
N3	0.0300 (11)	0.0318 (11)	0.0427 (13)	0.0032 (9)	0.0117 (10)	0.0062 (10)
C1	0.0273 (11)	0.0239 (10)	0.0225 (10)	−0.0041 (9)	−0.0019 (9)	−0.0004 (9)
C2	0.0279 (11)	0.0224 (10)	0.0275 (11)	−0.0021 (9)	−0.0009 (9)	−0.0003 (9)
C3	0.0330 (12)	0.0252 (11)	0.0241 (11)	−0.0025 (9)	0.0028 (9)	−0.0035 (9)
C4	0.0271 (11)	0.0329 (13)	0.0324 (13)	0.0019 (9)	0.0016 (9)	−0.0002 (11)
C5	0.0337 (12)	0.0368 (14)	0.0233 (10)	−0.0035 (11)	−0.0046 (9)	0.0038 (10)
C6	0.0236 (10)	0.0202 (10)	0.0238 (11)	0.0000 (7)	0.0009 (8)	0.0023 (9)
C7	0.0245 (10)	0.0252 (11)	0.0254 (10)	0.0001 (8)	−0.0016 (9)	0.0033 (10)
C8	0.0296 (11)	0.0260 (11)	0.0246 (11)	−0.0015 (9)	0.0037 (9)	0.0019 (9)
C9	0.0250 (11)	0.0260 (11)	0.0312 (12)	0.0019 (9)	0.0073 (9)	0.0059 (10)
C10	0.0206 (10)	0.0297 (11)	0.0345 (13)	−0.0020 (9)	−0.0014 (9)	0.0060 (10)
C11	0.0270 (10)	0.0240 (11)	0.0268 (11)	−0.0025 (9)	−0.0042 (9)	0.0012 (9)

O1—N3	1.222 (3)	C4—H4C	0.9800
O2—N3	1.228 (3)	C5—H5A	0.9800
N1—C1	1.372 (3)	C5—H5B	0.9800
N1—N2	1.376 (3)	C5—H5C	0.9800
N1—C6	1.410 (3)	C6—C7	1.396 (3)
N2—C2	1.325 (3)	C6—C11	1.399 (3)
N3—C9	1.461 (3)	C7—C8	1.384 (3)
C1—C3	1.366 (3)	C7—H7	0.9500
C1—C5	1.495 (3)	C8—C9	1.390 (3)
C2—C3	1.414 (3)	C8—H8	0.9500
C2—C4	1.498 (3)	C9—C10	1.379 (4)
C3—H3	0.9500	C10—C11	1.382 (3)
C4—H4A	0.9800	C10—H10	0.9500
C4—H4B	0.9800	C11—H11	0.9500
C1—N1—N2	112.11 (19)	C1—C5—H5B	109.5
C1—N1—C6	129.48 (19)	H5A—C5—H5B	109.5
N2—N1—C6	118.37 (19)	C1—C5—H5C	109.5
C2—N2—N1	104.56 (19)	H5A—C5—H5C	109.5
O1—N3—O2	123.2 (2)	H5B—C5—H5C	109.5
O1—N3—C9	119.0 (2)	C7—C6—C11	120.4 (2)
O2—N3—C9	117.8 (2)	C7—C6—N1	118.8 (2)
C3—C1—N1	105.7 (2)	C11—C6—N1	120.8 (2)
C3—C1—C5	129.1 (2)	C8—C7—C6	120.0 (2)
N1—C1—C5	125.0 (2)	C8—C7—H7	120.0
N2—C2—C3	111.2 (2)	C6—C7—H7	120.0
N2—C2—C4	121.4 (2)	C7—C8—C9	118.6 (2)
C3—C2—C4	127.4 (2)	C7—C8—H8	120.7
C1—C3—C2	106.4 (2)	C9—C8—H8	120.7
C1—C3—H3	126.8	C10—C9—C8	122.1 (2)
C2—C3—H3	126.8	C10—C9—N3	119.5 (2)
C2—C4—H4A	109.5	C8—C9—N3	118.4 (2)
C2—C4—H4B	109.5	C9—C10—C11	119.4 (2)
H4A—C4—H4B	109.5	C9—C10—H10	120.3
C2—C4—H4C	109.5	C11—C10—H10	120.3
H4A—C4—H4C	109.5	C10—C11—C6	119.5 (2)
H4B—C4—H4C	109.5	C10—C11—H11	120.3
C1—C5—H5A	109.5	C6—C11—H11	120.3
C1—N1—N2—C2	−1.6 (2)	N2—N1—C6—C11	−148.7 (2)
C6—N1—N2—C2	−179.38 (19)	C11—C6—C7—C8	−0.3 (3)
N2—N1—C1—C3	1.4 (3)	N1—C6—C7—C8	−178.8 (2)
C6—N1—C1—C3	178.9 (2)	C6—C7—C8—C9	−1.2 (3)
N2—N1—C1—C5	−174.1 (2)	C7—C8—C9—C10	1.1 (4)
C6—N1—C1—C5	3.4 (4)	C7—C8—C9—N3	−176.4 (2)
N1—N2—C2—C3	1.1 (2)	O1—N3—C9—C10	176.0 (2)
N1—N2—C2—C4	−179.9 (2)	O2—N3—C9—C10	−5.4 (3)
N1—C1—C3—C2	−0.7 (3)	O1—N3—C9—C8	−6.5 (3)
C5—C1—C3—C2	174.6 (2)	O2—N3—C9—C8	172.1 (2)
N2—C2—C3—C1	−0.3 (3)	C8—C9—C10—C11	0.5 (4)
C4—C2—C3—C1	−179.2 (2)	N3—C9—C10—C11	178.0 (2)
C1—N1—C6—C7	−147.5 (2)	C9—C10—C11—C6	−2.0 (3)
N2—N1—C6—C7	29.9 (3)	C7—C6—C11—C10	1.9 (3)
C1—N1—C6—C11	34.0 (3)	N1—C6—C11—C10	−179.6 (2)