Ethyl 1-benzyl-3-(4-bromo-phen-yl)-1H-pyrazole-5-carboxyl-ate.

In the title compound, C(19)H(17)BrN(2)O(2), the pyrazole ring makes dihedral angles of 88.00 (16) and 5.78 (13)° with the phenyl and bromo-phenyl rings, respectively. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds.

Related literature

For the pharmacological activity of pyrazole compounds and applications of nitro­gen-containing heterocyclic compounds, see: Ge et al. (2009 ▶, 2011 ▶). For the related structures, see: Han et al. (2011 ▶); Ge et al. (2007 ▶); Li et al. (2011 ▶).

Experimental

Crystal data

C19H17BrN2O2

M = 385.26

Monoclinic,

a = 10.5656 (13) Å

b = 15.3433 (19) Å

c = 11.5706 (14) Å

β = 111.506 (2)°

V = 1745.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 2.37 mm−1

T = 298 K

0.22 × 0.16 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996) ▶ T min = 0.624, T max = 0.764

8955 measured reflections

3089 independent reflections

2332 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.02

3089 reflections

217 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.70 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/S1600536811024986/wn2438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811024986/wn2438Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811024986/wn2438Isup3.cml

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

C19H17BrN2O2	F(000) = 784
Mr = 385.26	Dx = 1.466 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3103 reflections
a = 10.5656 (13) Å	θ = 2.2–25.3°
b = 15.3433 (19) Å	µ = 2.37 mm−1
c = 11.5706 (14) Å	T = 298 K
β = 111.506 (2)°	Block, colorless
V = 1745.1 (4) Å3	0.22 × 0.16 × 0.12 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3089 independent reflections
Radiation source: fine-focus sealed tube	2332 reflections with I > 2σ(I)
graphite	Rint = 0.022
phi and ω scans	θmax = 25.1°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.624, Tmax = 0.764	k = −18→17
8955 measured reflections	l = −13→11

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0415P)2 + 0.8018P] where P = (Fo2 + 2Fc2)/3
3089 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.70 e Å−3

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
Br1	0.14954 (3)	0.23557 (2)	0.33861 (3)	0.07268 (15)
N1	0.5993 (2)	0.57103 (14)	0.88561 (19)	0.0464 (5)
N2	0.4883 (2)	0.52724 (13)	0.81156 (19)	0.0458 (5)
O1	0.87411 (19)	0.63973 (15)	1.00922 (19)	0.0689 (6)
O2	0.92884 (17)	0.57135 (12)	0.86274 (18)	0.0552 (5)
C1	0.2646 (3)	0.31434 (16)	0.4583 (2)	0.0460 (6)
C2	0.2191 (3)	0.35288 (18)	0.5429 (3)	0.0540 (7)
H2	0.1316	0.3421	0.5405	0.065*
C3	0.3052 (3)	0.40806 (17)	0.6317 (3)	0.0495 (6)
H3	0.2748	0.4342	0.6892	0.059*
C4	0.4364 (2)	0.42517 (14)	0.6366 (2)	0.0385 (5)
C5	0.4785 (3)	0.38498 (17)	0.5496 (2)	0.0501 (6)
H5	0.5657	0.3955	0.5509	0.060*
C6	0.3933 (3)	0.32961 (18)	0.4609 (3)	0.0540 (7)
H6	0.4231	0.3029	0.4033	0.065*
C7	0.5294 (2)	0.48270 (15)	0.7316 (2)	0.0391 (5)
C8	0.6665 (2)	0.49904 (16)	0.7551 (2)	0.0425 (6)
H8	0.7185	0.4762	0.7126	0.051*
C9	0.7089 (2)	0.55554 (16)	0.8535 (2)	0.0428 (6)
C10	0.8439 (3)	0.59442 (17)	0.9187 (3)	0.0482 (6)
C11	1.0643 (3)	0.6089 (2)	0.9142 (3)	0.0624 (8)
H11A	1.1091	0.5912	1.0002	0.075*
H11B	1.0590	0.6721	0.9111	0.075*
C12	1.1416 (3)	0.5767 (3)	0.8380 (4)	0.0874 (12)
H12A	1.1463	0.5142	0.8421	0.131*
H12B	1.2319	0.6004	0.8696	0.131*
H12C	1.0963	0.5946	0.7533	0.131*
C13	0.5871 (3)	0.62843 (18)	0.9823 (3)	0.0534 (7)
H13A	0.6578	0.6137	1.0610	0.064*
H13B	0.5000	0.6180	0.9900	0.064*
C14	0.5983 (2)	0.72389 (17)	0.9565 (2)	0.0447 (6)
C15	0.5372 (3)	0.7587 (2)	0.8389 (3)	0.0596 (8)
H15	0.4890	0.7225	0.7730	0.071*
C16	0.5469 (4)	0.8471 (2)	0.8179 (3)	0.0712 (9)
H16	0.5064	0.8695	0.7381	0.085*
C17	0.6163 (4)	0.9013 (2)	0.9148 (3)	0.0719 (9)
H17	0.6217	0.9607	0.9010	0.086*
C18	0.6778 (3)	0.8676 (2)	1.0323 (3)	0.0677 (9)
H18	0.7254	0.9041	1.0981	0.081*
C19	0.6687 (3)	0.77974 (19)	1.0524 (3)	0.0551 (7)
H19	0.7108	0.7575	1.1321	0.066*

	U11	U22	U33	U12	U13	U23
Br1	0.0671 (2)	0.0617 (2)	0.0738 (2)	−0.01026 (15)	0.00757 (17)	−0.02063 (16)
N1	0.0462 (12)	0.0457 (12)	0.0486 (13)	−0.0028 (10)	0.0190 (10)	−0.0077 (10)
N2	0.0414 (12)	0.0458 (12)	0.0506 (13)	−0.0048 (9)	0.0172 (10)	−0.0060 (10)
O1	0.0518 (12)	0.0864 (16)	0.0595 (13)	−0.0039 (11)	0.0099 (10)	−0.0261 (12)
O2	0.0386 (10)	0.0590 (12)	0.0668 (12)	−0.0089 (8)	0.0182 (9)	−0.0150 (9)
C1	0.0467 (15)	0.0361 (14)	0.0478 (15)	−0.0021 (11)	0.0084 (12)	−0.0007 (11)
C2	0.0434 (15)	0.0511 (16)	0.0680 (18)	−0.0061 (12)	0.0210 (14)	−0.0079 (13)
C3	0.0442 (15)	0.0488 (15)	0.0588 (17)	0.0000 (12)	0.0228 (13)	−0.0062 (13)
C4	0.0376 (13)	0.0327 (12)	0.0434 (14)	0.0027 (10)	0.0128 (11)	0.0044 (10)
C5	0.0447 (15)	0.0530 (16)	0.0555 (16)	−0.0042 (12)	0.0221 (13)	−0.0065 (13)
C6	0.0620 (18)	0.0511 (16)	0.0534 (17)	−0.0033 (13)	0.0263 (14)	−0.0100 (13)
C7	0.0390 (13)	0.0329 (12)	0.0447 (14)	0.0017 (10)	0.0146 (11)	0.0020 (10)
C8	0.0398 (14)	0.0411 (14)	0.0489 (15)	0.0010 (11)	0.0190 (12)	−0.0037 (11)
C9	0.0384 (13)	0.0422 (14)	0.0472 (15)	0.0021 (11)	0.0152 (11)	0.0003 (11)
C10	0.0438 (15)	0.0464 (15)	0.0495 (16)	0.0022 (12)	0.0111 (13)	−0.0001 (13)
C11	0.0400 (15)	0.0645 (19)	0.075 (2)	−0.0077 (13)	0.0121 (14)	−0.0046 (15)
C12	0.055 (2)	0.107 (3)	0.110 (3)	−0.0105 (19)	0.041 (2)	−0.007 (2)
C13	0.0558 (17)	0.0602 (17)	0.0497 (16)	−0.0044 (14)	0.0259 (14)	−0.0095 (13)
C14	0.0397 (14)	0.0543 (16)	0.0442 (15)	0.0028 (11)	0.0202 (12)	−0.0090 (12)
C15	0.0621 (19)	0.070 (2)	0.0467 (17)	0.0058 (15)	0.0196 (14)	−0.0094 (14)
C16	0.086 (2)	0.076 (2)	0.0583 (19)	0.0211 (19)	0.0350 (18)	0.0132 (17)
C17	0.093 (2)	0.0549 (19)	0.091 (3)	0.0002 (17)	0.061 (2)	0.0007 (18)
C18	0.072 (2)	0.061 (2)	0.078 (2)	−0.0158 (16)	0.0364 (18)	−0.0192 (17)
C19	0.0540 (17)	0.0639 (19)	0.0467 (16)	−0.0058 (14)	0.0176 (13)	−0.0096 (13)

Br1—C1	1.903 (2)	C9—C10	1.474 (4)
N1—N2	1.351 (3)	C11—C12	1.489 (4)
N1—C9	1.360 (3)	C11—H11A	0.9700
N1—C13	1.466 (3)	C11—H11B	0.9700
N2—C7	1.344 (3)	C12—H12A	0.9600
O1—C10	1.199 (3)	C12—H12B	0.9600
O2—C10	1.332 (3)	C12—H12C	0.9600
O2—C11	1.453 (3)	C13—C14	1.508 (4)
C1—C6	1.369 (4)	C13—H13A	0.9700
C1—C2	1.371 (4)	C13—H13B	0.9700
C2—C3	1.384 (4)	C14—C15	1.382 (4)
C2—H2	0.9300	C14—C19	1.383 (4)
C3—C4	1.391 (3)	C15—C16	1.387 (4)
C3—H3	0.9300	C15—H15	0.9300
C4—C5	1.386 (3)	C16—C17	1.373 (5)
C4—C7	1.470 (3)	C16—H16	0.9300
C5—C6	1.381 (4)	C17—C18	1.375 (5)
C5—H5	0.9300	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.378 (4)
C7—C8	1.395 (3)	C18—H18	0.9300
C8—C9	1.369 (3)	C19—H19	0.9300
C8—H8	0.9300
N2—N1—C9	111.58 (19)	O2—C11—H11A	110.3
N2—N1—C13	118.9 (2)	C12—C11—H11A	110.3
C9—N1—C13	129.5 (2)	O2—C11—H11B	110.3
C7—N2—N1	105.40 (19)	C12—C11—H11B	110.3
C10—O2—C11	115.6 (2)	H11A—C11—H11B	108.5
C6—C1—C2	121.0 (2)	C11—C12—H12A	109.5
C6—C1—Br1	119.2 (2)	C11—C12—H12B	109.5
C2—C1—Br1	119.7 (2)	H12A—C12—H12B	109.5
C1—C2—C3	119.1 (2)	C11—C12—H12C	109.5
C1—C2—H2	120.4	H12A—C12—H12C	109.5
C3—C2—H2	120.4	H12B—C12—H12C	109.5
C2—C3—C4	121.3 (2)	N1—C13—C14	113.4 (2)
C2—C3—H3	119.3	N1—C13—H13A	108.9
C4—C3—H3	119.3	C14—C13—H13A	108.9
C5—C4—C3	117.8 (2)	N1—C13—H13B	108.9
C5—C4—C7	120.4 (2)	C14—C13—H13B	108.9
C3—C4—C7	121.8 (2)	H13A—C13—H13B	107.7
C6—C5—C4	121.2 (2)	C15—C14—C19	118.0 (3)
C6—C5—H5	119.4	C15—C14—C13	121.9 (2)
C4—C5—H5	119.4	C19—C14—C13	120.1 (3)
C1—C6—C5	119.5 (3)	C14—C15—C16	120.9 (3)
C1—C6—H6	120.2	C14—C15—H15	119.6
C5—C6—H6	120.2	C16—C15—H15	119.6
N2—C7—C8	110.4 (2)	C17—C16—C15	120.0 (3)
N2—C7—C4	121.6 (2)	C17—C16—H16	120.0
C8—C7—C4	128.0 (2)	C15—C16—H16	120.0
C9—C8—C7	106.0 (2)	C16—C17—C18	119.8 (3)
C9—C8—H8	127.0	C16—C17—H17	120.1
C7—C8—H8	127.0	C18—C17—H17	120.1
N1—C9—C8	106.6 (2)	C17—C18—C19	119.9 (3)
N1—C9—C10	123.4 (2)	C17—C18—H18	120.1
C8—C9—C10	130.0 (2)	C19—C18—H18	120.1
O1—C10—O2	124.6 (2)	C18—C19—C14	121.4 (3)
O1—C10—C9	125.4 (3)	C18—C19—H19	119.3
O2—C10—C9	110.0 (2)	C14—C19—H19	119.3
O2—C11—C12	107.3 (2)
C9—N1—N2—C7	0.4 (3)	C13—N1—C9—C10	2.5 (4)
C13—N1—N2—C7	178.5 (2)	C7—C8—C9—N1	0.1 (3)
C6—C1—C2—C3	0.1 (4)	C7—C8—C9—C10	179.4 (3)
Br1—C1—C2—C3	178.2 (2)	C11—O2—C10—O1	−3.4 (4)
C1—C2—C3—C4	0.1 (4)	C11—O2—C10—C9	177.1 (2)
C2—C3—C4—C5	−0.1 (4)	N1—C9—C10—O1	3.8 (4)
C2—C3—C4—C7	−179.1 (2)	C8—C9—C10—O1	−175.4 (3)
C3—C4—C5—C6	−0.1 (4)	N1—C9—C10—O2	−176.6 (2)
C7—C4—C5—C6	178.9 (2)	C8—C9—C10—O2	4.1 (4)
C2—C1—C6—C5	−0.3 (4)	C10—O2—C11—C12	−179.0 (3)
Br1—C1—C6—C5	−178.4 (2)	N2—N1—C13—C14	−110.3 (3)
C4—C5—C6—C1	0.3 (4)	C9—N1—C13—C14	67.4 (4)
N1—N2—C7—C8	−0.4 (3)	N1—C13—C14—C15	40.9 (4)
N1—N2—C7—C4	178.8 (2)	N1—C13—C14—C19	−140.5 (2)
C5—C4—C7—N2	175.3 (2)	C19—C14—C15—C16	0.2 (4)
C3—C4—C7—N2	−5.7 (4)	C13—C14—C15—C16	178.9 (3)
C5—C4—C7—C8	−5.7 (4)	C14—C15—C16—C17	−0.9 (5)
C3—C4—C7—C8	173.3 (2)	C15—C16—C17—C18	0.9 (5)
N2—C7—C8—C9	0.2 (3)	C16—C17—C18—C19	−0.4 (5)
C4—C7—C8—C9	−178.9 (2)	C17—C18—C19—C14	−0.2 (5)
N2—N1—C9—C8	−0.3 (3)	C15—C14—C19—C18	0.3 (4)
C13—N1—C9—C8	−178.1 (2)	C13—C14—C19—C18	−178.4 (3)
N2—N1—C9—C10	−179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O1i	0.93	2.50	3.369 (4)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O1i	0.93	2.50	3.369 (4)	155

Symmetry code: (i) .