3-(4-Bromo-phen-yl)-1-phenyl-1H-pyrazole-4-carbaldehyde.

In the title compound, C(16)H(11)BrN(2)O, the phenyl and chloro-benzene rings are twisted out of the mean plane of the pyrazole ring, forming dihedral angles of 13.70 (10) and 36.48 (10)°, respectively. The carbaldehyde group is also twisted out of the pyrazole plane [the C-C-C-O torsion angle is 7.9 (3)°]. A helical supra-molecular chain along the b axis and mediated by C-H⋯O inter-actions is the most prominent feature of the crystal packing.

Related literature

For background details and biological applications of pyrazoles, see: Kaushik et al. (2010 ▶); Ali et al. (2007 ▶); Krishnamurthy et al. (2004 ▶). For a related structure, see: Asiri et al. (2011 ▶).

Experimental

Crystal data

C16H11BrN2O

M = 327.18

Monoclinic,

a = 17.7233 (4) Å

b = 3.8630 (1) Å

c = 20.4224 (5) Å

β = 110.137 (3)°

V = 1312.75 (6) Å3

Z = 4

Cu Kα radiation

μ = 4.23 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.418, T max = 0.569

4619 measured reflections

2593 independent reflections

2542 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.069

S = 1.02

2593 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.66 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811036841/hb6403sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036841/hb6403Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036841/hb6403Isup3.cml

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

C16H11BrN2O	F(000) = 656
Mr = 327.18	Dx = 1.655 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 3680 reflections
a = 17.7233 (4) Å	θ = 2.7–74.1°
b = 3.8630 (1) Å	µ = 4.23 mm−1
c = 20.4224 (5) Å	T = 100 K
β = 110.137 (3)°	Prism, colourless
V = 1312.75 (6) Å3	0.25 × 0.20 × 0.15 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	2593 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2542 reflections with I > 2σ(I)
Mirror	Rint = 0.012
Detector resolution: 10.4041 pixels mm-1	θmax = 74.3°, θmin = 2.9°
ω scans	h = −21→21
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −4→4
Tmin = 0.418, Tmax = 0.569	l = −19→25
4619 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.069	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0432P)2 + 1.2934P] where P = (Fo2 + 2Fc2)/3
2593 reflections	(Δ/σ)max = 0.004
181 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.66 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
Br1	0.979494 (11)	0.14952 (5)	1.111751 (9)	0.01554 (9)
O1	0.66107 (9)	0.4209 (4)	0.71084 (7)	0.0183 (3)
N1	0.54596 (9)	0.8378 (4)	0.84419 (8)	0.0106 (3)
N2	0.60504 (9)	0.7642 (4)	0.90629 (8)	0.0114 (3)
C1	0.47250 (10)	0.9916 (5)	0.84392 (9)	0.0112 (3)
C2	0.45581 (11)	0.9963 (5)	0.90561 (10)	0.0146 (4)
H2	0.4929	0.9008	0.9471	0.018*
C3	0.38437 (12)	1.1422 (5)	0.90583 (11)	0.0170 (4)
H3	0.3729	1.1496	0.9480	0.020*
C4	0.32952 (12)	1.2773 (5)	0.84520 (11)	0.0169 (4)
H4	0.2805	1.3744	0.8456	0.020*
C5	0.34673 (11)	1.2698 (5)	0.78370 (10)	0.0165 (4)
H5	0.3092	1.3617	0.7421	0.020*
C6	0.41865 (12)	1.1284 (5)	0.78272 (10)	0.0148 (4)
H6	0.4307	1.1255	0.7408	0.018*
C7	0.73867 (11)	0.5078 (5)	0.94282 (9)	0.0112 (4)
C8	0.73831 (12)	0.3647 (5)	1.00557 (10)	0.0128 (4)
H8	0.6888	0.3396	1.0135	0.015*
C9	0.80911 (12)	0.2589 (5)	1.05641 (9)	0.0141 (4)
H9	0.8085	0.1639	1.0991	0.017*
C10	0.88090 (11)	0.2942 (5)	1.04391 (10)	0.0135 (4)
C11	0.88296 (11)	0.4357 (5)	0.98216 (10)	0.0146 (4)
H11	0.9326	0.4580	0.9744	0.018*
C12	0.81210 (11)	0.5442 (5)	0.93190 (9)	0.0133 (4)
H12	0.8133	0.6440	0.8898	0.016*
C13	0.56590 (11)	0.7418 (5)	0.78887 (9)	0.0117 (3)
H13	0.5340	0.7694	0.7411	0.014*
C14	0.64162 (11)	0.5954 (5)	0.81478 (10)	0.0115 (4)
C15	0.66323 (11)	0.6177 (5)	0.88888 (9)	0.0105 (4)
C16	0.68436 (11)	0.4243 (5)	0.77447 (10)	0.0135 (4)
H16	0.7332	0.3085	0.7991	0.016*

	U11	U22	U33	U12	U13	U23
Br1	0.01392 (13)	0.01863 (13)	0.01135 (12)	0.00306 (7)	0.00088 (9)	0.00292 (7)
O1	0.0176 (7)	0.0277 (7)	0.0116 (6)	−0.0046 (6)	0.0076 (5)	−0.0054 (6)
N1	0.0085 (7)	0.0138 (8)	0.0094 (7)	0.0002 (6)	0.0029 (6)	−0.0001 (5)
N2	0.0103 (7)	0.0144 (7)	0.0089 (7)	0.0004 (6)	0.0024 (6)	0.0000 (6)
C1	0.0089 (8)	0.0110 (9)	0.0143 (8)	−0.0015 (7)	0.0048 (7)	−0.0025 (7)
C2	0.0142 (9)	0.0164 (9)	0.0134 (8)	0.0000 (7)	0.0051 (7)	−0.0003 (7)
C3	0.0168 (10)	0.0180 (10)	0.0195 (10)	−0.0001 (7)	0.0103 (8)	−0.0031 (7)
C4	0.0130 (9)	0.0141 (9)	0.0246 (10)	−0.0002 (8)	0.0076 (8)	−0.0026 (8)
C5	0.0113 (9)	0.0161 (9)	0.0192 (9)	0.0009 (8)	0.0014 (7)	0.0006 (8)
C6	0.0139 (9)	0.0172 (10)	0.0136 (9)	−0.0002 (7)	0.0051 (8)	0.0002 (7)
C7	0.0107 (8)	0.0111 (9)	0.0113 (8)	0.0002 (7)	0.0032 (7)	−0.0014 (7)
C8	0.0131 (9)	0.0150 (9)	0.0127 (9)	−0.0004 (7)	0.0075 (7)	−0.0008 (7)
C9	0.0190 (9)	0.0149 (9)	0.0097 (8)	0.0004 (8)	0.0067 (7)	0.0011 (7)
C10	0.0129 (9)	0.0141 (9)	0.0110 (8)	0.0007 (7)	0.0010 (7)	−0.0009 (7)
C11	0.0106 (9)	0.0200 (9)	0.0138 (9)	−0.0019 (7)	0.0049 (7)	0.0012 (8)
C12	0.0135 (9)	0.0167 (9)	0.0108 (8)	−0.0006 (7)	0.0053 (7)	0.0018 (7)
C13	0.0123 (8)	0.0145 (9)	0.0082 (8)	−0.0018 (7)	0.0034 (7)	−0.0014 (7)
C14	0.0119 (8)	0.0132 (8)	0.0103 (8)	−0.0016 (7)	0.0051 (7)	−0.0010 (7)
C15	0.0114 (9)	0.0117 (8)	0.0094 (9)	−0.0026 (6)	0.0048 (7)	−0.0009 (6)
C16	0.0118 (8)	0.0168 (9)	0.0134 (9)	−0.0020 (7)	0.0064 (7)	−0.0031 (7)

Br1—C10	1.9023 (19)	C7—C8	1.398 (3)
O1—C16	1.220 (2)	C7—C12	1.401 (2)
N1—C13	1.347 (2)	C7—C15	1.472 (3)
N1—N2	1.368 (2)	C8—C9	1.387 (3)
N1—C1	1.429 (2)	C8—H8	0.9500
N2—C15	1.328 (2)	C9—C10	1.388 (3)
C1—C6	1.390 (3)	C9—H9	0.9500
C1—C2	1.390 (3)	C10—C11	1.386 (3)
C2—C3	1.387 (3)	C11—C12	1.385 (3)
C2—H2	0.9500	C11—H11	0.9500
C3—C4	1.386 (3)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.383 (3)
C4—C5	1.391 (3)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.430 (2)
C5—C6	1.393 (3)	C14—C16	1.455 (3)
C5—H5	0.9500	C16—H16	0.9500
C6—H6	0.9500
C13—N1—N2	112.47 (15)	C9—C8—H8	119.5
C13—N1—C1	127.81 (16)	C7—C8—H8	119.5
N2—N1—C1	119.70 (15)	C8—C9—C10	118.95 (17)
C15—N2—N1	104.93 (14)	C8—C9—H9	120.5
C6—C1—C2	121.05 (17)	C10—C9—H9	120.5
C6—C1—N1	120.28 (16)	C11—C10—C9	121.26 (17)
C2—C1—N1	118.67 (17)	C11—C10—Br1	118.24 (14)
C3—C2—C1	119.17 (18)	C9—C10—Br1	120.50 (14)
C3—C2—H2	120.4	C12—C11—C10	119.49 (17)
C1—C2—H2	120.4	C12—C11—H11	120.3
C2—C3—C4	120.68 (18)	C10—C11—H11	120.3
C2—C3—H3	119.7	C11—C12—C7	120.44 (17)
C4—C3—H3	119.7	C11—C12—H12	119.8
C3—C4—C5	119.61 (18)	C7—C12—H12	119.8
C3—C4—H4	120.2	N1—C13—C14	106.98 (16)
C5—C4—H4	120.2	N1—C13—H13	126.5
C4—C5—C6	120.48 (19)	C14—C13—H13	126.5
C4—C5—H5	119.8	C13—C14—C15	104.56 (16)
C6—C5—H5	119.8	C13—C14—C16	126.51 (17)
C1—C6—C5	118.99 (18)	C15—C14—C16	128.61 (17)
C1—C6—H6	120.5	N2—C15—C14	111.05 (16)
C5—C6—H6	120.5	N2—C15—C7	120.77 (16)
C8—C7—C12	118.90 (17)	C14—C15—C7	128.17 (16)
C8—C7—C15	120.71 (16)	O1—C16—C14	123.78 (18)
C12—C7—C15	120.40 (16)	O1—C16—H16	118.1
C9—C8—C7	120.97 (17)	C14—C16—H16	118.1
C13—N1—N2—C15	−0.1 (2)	Br1—C10—C11—C12	−179.81 (15)
C1—N1—N2—C15	178.39 (16)	C10—C11—C12—C7	−0.8 (3)
C13—N1—C1—C6	−14.2 (3)	C8—C7—C12—C11	0.9 (3)
N2—N1—C1—C6	167.59 (17)	C15—C7—C12—C11	−178.95 (18)
C13—N1—C1—C2	164.85 (18)	N2—N1—C13—C14	0.3 (2)
N2—N1—C1—C2	−13.4 (3)	C1—N1—C13—C14	−178.04 (17)
C6—C1—C2—C3	−0.4 (3)	N1—C13—C14—C15	−0.3 (2)
N1—C1—C2—C3	−179.44 (17)	N1—C13—C14—C16	173.58 (18)
C1—C2—C3—C4	1.0 (3)	N1—N2—C15—C14	−0.1 (2)
C2—C3—C4—C5	−0.7 (3)	N1—N2—C15—C7	178.76 (16)
C3—C4—C5—C6	−0.1 (3)	C13—C14—C15—N2	0.3 (2)
C2—C1—C6—C5	−0.4 (3)	C16—C14—C15—N2	−173.44 (19)
N1—C1—C6—C5	178.59 (18)	C13—C14—C15—C7	−178.49 (18)
C4—C5—C6—C1	0.7 (3)	C16—C14—C15—C7	7.8 (3)
C12—C7—C8—C9	−0.2 (3)	C8—C7—C15—N2	37.3 (3)
C15—C7—C8—C9	179.64 (17)	C12—C7—C15—N2	−142.86 (19)
C7—C8—C9—C10	−0.6 (3)	C8—C7—C15—C14	−143.99 (19)
C8—C9—C10—C11	0.7 (3)	C12—C7—C15—C14	35.8 (3)
C8—C9—C10—Br1	−179.51 (15)	C13—C14—C16—O1	7.9 (3)
C9—C10—C11—C12	0.0 (3)	C15—C14—C16—O1	−179.63 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1i	0.95	2.49	3.435 (2)	171
C16—H16···O1ii	0.95	2.46	3.288 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1i	0.95	2.49	3.435 (2)	171
C16—H16⋯O1ii	0.95	2.46	3.288 (3)	145

Symmetry codes: (i) ; (ii) .