3-(4-Bromo-phen-yl)-1-(4-chloro-benz-yl)-1H-pyrazole-5-carbaldehyde.

The title compound, C(17)H(12)BrClN(2)O, was synthesized by oxidation of [3-(4-bromo-phen-yl)-1-(4-chloro-benz-yl)-1H-pyrazol-5-yl]methanol under mild conditions. The pyrazole ring makes dihedral angles of 3.29 (9) and 74.91 (4)°, respectively, with the bromo-phenyl and chloro-phenyl rings.

Related literature

For applications of nitro­gen-containing heterocyclic compounds in the agrochemical and pharmaceutical fields, see: Ge et al. (2007 ▶, 2009 ▶, 2011 ▶). For the biological activity of some pyrazole derivatives belonging to this class of compounds, see: Xia et al. (2007 ▶). For a related compound, see: Hao et al. (2012 ▶).

Experimental

Crystal data

C17H12BrClN2O

M = 375.65

Triclinic,

a = 6.759 (5) Å

b = 10.061 (5) Å

c = 12.263 (5) Å

α = 109.080 (5)°

β = 94.521 (5)°

γ = 93.098 (5)°

V = 782.8 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.80 mm−1

T = 293 K

0.18 × 0.15 × 0.14 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.860, T max = 0.891

4563 measured reflections

3151 independent reflections

2410 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.104

S = 1.05

3151 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.50 e Å−3

Δρmin = −0.43 e Å−3

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812027298/bh2439sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812027298/bh2439Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812027298/bh2439Isup3.cml

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

C17H12BrClN2O	Z = 2
Mr = 375.65	F(000) = 376
Triclinic, P1	Dx = 1.594 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 6.759 (5) Å	Cell parameters from 5043 reflections
b = 10.061 (5) Å	θ = 0.9–28.3°
c = 12.263 (5) Å	µ = 2.80 mm−1
α = 109.080 (5)°	T = 293 K
β = 94.521 (5)°	Block, colourless
γ = 93.098 (5)°	0.18 × 0.15 × 0.14 mm
V = 782.8 (8) Å3

Bruker SMART APEX CCD area-detector diffractometer	3151 independent reflections
Radiation source: fine-focus sealed tube	2410 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
φ and ω scans	θmax = 26.4°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→4
Tmin = 0.860, Tmax = 0.891	k = −12→11
4563 measured reflections	l = −13→15

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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.104	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.068P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3151 reflections	Δρmax = 0.50 e Å−3
200 parameters	Δρmin = −0.43 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 constraints	Extinction coefficient: 0.019 (3)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	1.33740 (5)	−0.03239 (4)	−0.36464 (3)	0.07272 (18)
C1	0.2091 (4)	0.4007 (3)	0.0013 (3)	0.0622 (7)
H1	0.1666	0.4399	−0.0546	0.075*
C2	0.3841 (4)	0.3206 (3)	−0.0184 (2)	0.0488 (6)
C3	0.4976 (4)	0.2937 (3)	−0.1103 (2)	0.0486 (6)
H3	0.4800	0.3243	−0.1740	0.058*
C4	0.6443 (4)	0.2110 (2)	−0.0884 (2)	0.0439 (6)
C5	0.4145 (4)	0.2593 (3)	0.1680 (2)	0.0529 (6)
H5A	0.4587	0.1766	0.1837	0.063*
H5B	0.2711	0.2569	0.1693	0.063*
C6	0.5106 (4)	0.3908 (3)	0.2619 (2)	0.0476 (6)
C7	0.3960 (4)	0.4906 (3)	0.3274 (2)	0.0533 (7)
H7	0.2582	0.4783	0.3110	0.064*
C8	0.4806 (5)	0.6079 (3)	0.4166 (2)	0.0588 (7)
H8	0.4013	0.6738	0.4601	0.071*
C9	0.7135 (5)	0.4130 (4)	0.2855 (3)	0.0772 (10)
H9	0.7940	0.3483	0.2415	0.093*
C10	0.7995 (5)	0.5311 (4)	0.3743 (3)	0.0867 (11)
H10	0.9374	0.5459	0.3893	0.104*
C11	0.6828 (5)	0.6255 (3)	0.4398 (2)	0.0606 (8)
C12	0.8084 (4)	0.1521 (3)	−0.1560 (2)	0.0449 (6)
C13	0.9331 (4)	0.0666 (3)	−0.1209 (2)	0.0580 (7)
H13	0.9110	0.0459	−0.0541	0.070*
C14	1.0906 (5)	0.0105 (3)	−0.1818 (3)	0.0624 (8)
H14	1.1735	−0.0465	−0.1562	0.075*
C15	0.8436 (5)	0.1785 (3)	−0.2571 (3)	0.0591 (7)
H15	0.7611	0.2351	−0.2835	0.071*
C16	0.9981 (5)	0.1229 (3)	−0.3193 (3)	0.0616 (7)
H16	1.0186	0.1408	−0.3875	0.074*
C17	1.1211 (4)	0.0411 (3)	−0.2803 (2)	0.0497 (6)
Cl1	0.79191 (16)	0.76908 (10)	0.55587 (7)	0.0864 (3)
N1	0.4642 (3)	0.2545 (2)	0.05291 (18)	0.0478 (5)
N2	0.6237 (3)	0.1883 (2)	0.01222 (19)	0.0482 (5)
O1	0.1149 (3)	0.4203 (3)	0.0836 (2)	0.0785 (6)

	U11	U22	U33	U12	U13	U23
Br1	0.0582 (2)	0.0828 (3)	0.0653 (2)	0.01627 (16)	0.02256 (15)	0.00339 (16)
C1	0.0485 (16)	0.0687 (18)	0.0609 (17)	0.0207 (14)	−0.0006 (14)	0.0088 (14)
C2	0.0431 (14)	0.0466 (13)	0.0507 (14)	0.0101 (11)	0.0009 (11)	0.0079 (11)
C3	0.0502 (15)	0.0489 (14)	0.0447 (14)	0.0116 (12)	−0.0003 (11)	0.0127 (11)
C4	0.0457 (14)	0.0406 (12)	0.0438 (13)	0.0081 (10)	0.0052 (11)	0.0110 (10)
C5	0.0530 (16)	0.0523 (15)	0.0565 (16)	0.0091 (12)	0.0201 (12)	0.0183 (12)
C6	0.0464 (15)	0.0530 (14)	0.0476 (14)	0.0083 (11)	0.0178 (11)	0.0186 (12)
C7	0.0535 (16)	0.0626 (17)	0.0469 (14)	0.0163 (13)	0.0160 (12)	0.0181 (13)
C8	0.071 (2)	0.0601 (17)	0.0475 (15)	0.0200 (14)	0.0202 (13)	0.0154 (13)
C9	0.0508 (18)	0.079 (2)	0.080 (2)	0.0106 (15)	0.0246 (16)	−0.0071 (17)
C10	0.0503 (19)	0.100 (3)	0.088 (3)	−0.0059 (18)	0.0204 (17)	−0.001 (2)
C11	0.076 (2)	0.0576 (16)	0.0471 (15)	−0.0060 (14)	0.0220 (14)	0.0137 (13)
C12	0.0445 (14)	0.0426 (13)	0.0452 (13)	0.0060 (11)	0.0065 (11)	0.0107 (11)
C13	0.0630 (18)	0.0687 (18)	0.0516 (15)	0.0275 (14)	0.0175 (13)	0.0263 (14)
C14	0.0639 (18)	0.0686 (18)	0.0604 (17)	0.0303 (15)	0.0158 (14)	0.0232 (15)
C15	0.0572 (17)	0.0703 (18)	0.0621 (17)	0.0221 (14)	0.0133 (14)	0.0345 (15)
C16	0.0671 (19)	0.0727 (19)	0.0515 (16)	0.0130 (15)	0.0179 (14)	0.0254 (14)
C17	0.0448 (14)	0.0493 (14)	0.0469 (14)	0.0064 (11)	0.0103 (11)	0.0035 (11)
Cl1	0.1054 (7)	0.0785 (6)	0.0600 (5)	−0.0247 (5)	0.0211 (4)	0.0047 (4)
N1	0.0454 (12)	0.0472 (11)	0.0491 (12)	0.0106 (9)	0.0109 (9)	0.0115 (10)
N2	0.0470 (12)	0.0473 (12)	0.0527 (13)	0.0162 (9)	0.0148 (10)	0.0156 (10)
O1	0.0548 (13)	0.1008 (17)	0.0737 (15)	0.0337 (12)	0.0132 (11)	0.0150 (13)

Br1—C17	1.900 (3)	C8—C11	1.363 (4)
C1—O1	1.203 (4)	C8—H8	0.9300
C1—C2	1.459 (4)	C9—C10	1.384 (5)
C1—H1	0.9300	C9—H9	0.9300
C2—N1	1.358 (3)	C10—C11	1.361 (5)
C2—C3	1.376 (4)	C10—H10	0.9300
C3—C4	1.393 (4)	C11—Cl1	1.741 (3)
C3—H3	0.9300	C12—C13	1.378 (4)
C4—N2	1.342 (3)	C12—C15	1.385 (4)
C4—C12	1.471 (4)	C13—C14	1.387 (4)
C5—N1	1.462 (3)	C13—H13	0.9300
C5—C6	1.514 (4)	C14—C17	1.368 (4)
C5—H5A	0.9700	C14—H14	0.9300
C5—H5B	0.9700	C15—C16	1.377 (4)
C6—C9	1.370 (4)	C15—H15	0.9300
C6—C7	1.382 (4)	C16—C17	1.365 (4)
C7—C8	1.379 (4)	C16—H16	0.9300
C7—H7	0.9300	N1—N2	1.342 (3)
O1—C1—C2	125.6 (3)	C10—C9—H9	119.8
O1—C1—H1	117.2	C11—C10—C9	120.2 (3)
C2—C1—H1	117.2	C11—C10—H10	119.9
N1—C2—C3	106.4 (2)	C9—C10—H10	119.9
N1—C2—C1	125.1 (3)	C10—C11—C8	120.7 (3)
C3—C2—C1	128.5 (3)	C10—C11—Cl1	119.8 (3)
C2—C3—C4	105.7 (2)	C8—C11—Cl1	119.5 (2)
C2—C3—H3	127.1	C13—C12—C15	117.2 (2)
C4—C3—H3	127.1	C13—C12—C4	120.7 (2)
N2—C4—C3	110.4 (2)	C15—C12—C4	122.1 (2)
N2—C4—C12	119.5 (2)	C12—C13—C14	122.3 (3)
C3—C4—C12	130.0 (2)	C12—C13—H13	118.9
N1—C5—C6	111.9 (2)	C14—C13—H13	118.9
N1—C5—H5A	109.2	C17—C14—C13	118.4 (3)
C6—C5—H5A	109.2	C17—C14—H14	120.8
N1—C5—H5B	109.2	C13—C14—H14	120.8
C6—C5—H5B	109.2	C16—C15—C12	121.4 (3)
H5A—C5—H5B	107.9	C16—C15—H15	119.3
C9—C6—C7	118.2 (3)	C12—C15—H15	119.3
C9—C6—C5	120.9 (2)	C17—C16—C15	119.6 (3)
C7—C6—C5	120.9 (3)	C17—C16—H16	120.2
C8—C7—C6	121.7 (3)	C15—C16—H16	120.2
C8—C7—H7	119.2	C16—C17—C14	121.1 (3)
C6—C7—H7	119.2	C16—C17—Br1	119.5 (2)
C11—C8—C7	118.8 (3)	C14—C17—Br1	119.4 (2)
C11—C8—H8	120.6	N2—N1—C2	111.8 (2)
C7—C8—H8	120.6	N2—N1—C5	118.3 (2)
C6—C9—C10	120.4 (3)	C2—N1—C5	129.5 (2)
C6—C9—H9	119.8	N1—N2—C4	105.6 (2)