Ethyl 1-(2-bromo-eth-yl)-3-(4-meth-oxy-phen-yl)-1H-pyrazole-5-carboxyl-ate.

In the title compound, C(15)H(17)BrN(2)O(3), the dihedral angle between the benzene and pyrazole rings is 5.63 (2)°. The crystal packing is stabilized by weak π-π stacking inter-actions [centroid-centroid distance = 3.927 (5) Å] and inter-molecular C-H⋯O and C-H⋯Br hydrogen bonds.

Related literature

For the biological activity of pyrazole compounds, see: Nagwa et al. (2012 ▶); Fahmy et al. (2012 ▶); Wang et al. (2011 ▶). For related structures, see: Dong et al. (2007 ▶); Hao et al. (2012 ▶).

Experimental

Crystal data

C15H17BrN2O3

M = 353.22

Monoclinic,

a = 24.691 (7) Å

b = 6.7678 (17) Å

c = 17.884 (5) Å

β = 97.184 (5)°

V = 2965.1 (13) Å3

Z = 8

Mo Kα radiation

μ = 2.78 mm−1

T = 113 K

0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009 ▶) T min = 0.606, T max = 0.697

13190 measured reflections

3501 independent reflections

2684 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.062

S = 1.02

3501 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear-SM Expert (Rigaku/MSC, 2009 ▶); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032370/rz2789sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032370/rz2789Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032370/rz2789Isup3.cml

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

C15H17BrN2O3	F(000) = 1440
Mr = 353.22	Dx = 1.583 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5090 reflections
a = 24.691 (7) Å	θ = 1.9–27.9°
b = 6.7678 (17) Å	µ = 2.78 mm−1
c = 17.884 (5) Å	T = 113 K
β = 97.184 (5)°	Prism, colourless
V = 2965.1 (13) Å3	0.20 × 0.18 × 0.14 mm
Z = 8

Rigaku Saturn CCD area-detector diffractometer	3501 independent reflections
Radiation source: rotating anode	2684 reflections with I > 2σ(I)
Multilayer monochromator	Rint = 0.033
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.3°
ω and φ scans	h = −32→30
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku/MSC, 2009)	k = −8→8
Tmin = 0.606, Tmax = 0.697	l = −23→20
13190 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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0311P)2] where P = (Fo2 + 2Fc2)/3
3501 reflections	(Δ/σ)max = 0.002
192 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.33 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	0.300383 (7)	−0.03804 (3)	0.042640 (10)	0.02615 (7)
O1	0.67705 (4)	0.29412 (19)	0.23584 (6)	0.0228 (3)
O2	0.32875 (5)	0.23696 (19)	−0.13898 (7)	0.0238 (3)
O3	0.41059 (5)	0.20467 (18)	−0.18169 (6)	0.0207 (3)
N1	0.43218 (5)	0.3178 (2)	0.06953 (8)	0.0196 (3)
N2	0.39195 (5)	0.3026 (2)	0.01120 (8)	0.0190 (3)
C1	0.72814 (7)	0.2707 (3)	0.20691 (11)	0.0295 (5)
H1A	0.7284	0.1445	0.1800	0.044*
H1B	0.7579	0.2722	0.2487	0.044*
H1C	0.7332	0.3792	0.1722	0.044*
C2	0.63072 (6)	0.2885 (3)	0.18455 (10)	0.0177 (4)
C3	0.58195 (7)	0.3140 (3)	0.21405 (10)	0.0215 (4)
H3	0.5821	0.3351	0.2666	0.026*
C4	0.53298 (7)	0.3087 (3)	0.16717 (10)	0.0212 (4)
H4	0.4998	0.3271	0.1881	0.025*
C5	0.53125 (6)	0.2770 (2)	0.08977 (9)	0.0162 (4)
C6	0.58044 (7)	0.2519 (3)	0.06120 (10)	0.0177 (4)
H6	0.5803	0.2300	0.0087	0.021*
C7	0.63016 (7)	0.2582 (3)	0.10763 (10)	0.0183 (4)
H7	0.6634	0.2418	0.0868	0.022*
C8	0.47850 (6)	0.2734 (2)	0.04107 (9)	0.0162 (4)
C9	0.46766 (7)	0.2326 (2)	−0.03645 (9)	0.0174 (4)
H9	0.4933	0.1983	−0.0697	0.021*
C10	0.41209 (7)	0.2527 (2)	−0.05401 (9)	0.0168 (4)
C11	0.37810 (7)	0.2314 (3)	−0.12779 (10)	0.0185 (4)
C12	0.38331 (7)	0.1924 (3)	−0.25861 (9)	0.0231 (4)
H12A	0.3609	0.3120	−0.2712	0.028*
H12B	0.3591	0.0753	−0.2645	0.028*
C13	0.42739 (7)	0.1759 (3)	−0.30925 (10)	0.0291 (5)
H13A	0.4507	0.2935	−0.3033	0.044*
H13B	0.4107	0.1654	−0.3618	0.044*
H13C	0.4495	0.0580	−0.2956	0.044*
C14	0.33701 (7)	0.3614 (3)	0.02402 (10)	0.0221 (4)
H14A	0.3127	0.3563	−0.0244	0.026*
H14B	0.3379	0.4997	0.0422	0.026*
C15	0.31375 (7)	0.2311 (3)	0.08072 (10)	0.0242 (4)
H15A	0.2790	0.2887	0.0929	0.029*
H15B	0.3395	0.2267	0.1278	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.02115 (10)	0.03091 (12)	0.02741 (12)	0.00178 (8)	0.00701 (8)	0.00177 (8)
O1	0.0133 (6)	0.0390 (8)	0.0157 (7)	−0.0006 (5)	0.0001 (5)	0.0010 (5)
O2	0.0158 (6)	0.0325 (8)	0.0219 (7)	−0.0010 (5)	−0.0023 (5)	0.0001 (5)
O3	0.0177 (6)	0.0287 (8)	0.0148 (7)	−0.0011 (5)	−0.0011 (5)	−0.0004 (5)
N1	0.0158 (7)	0.0257 (9)	0.0163 (8)	0.0004 (6)	−0.0020 (6)	0.0001 (6)
N2	0.0128 (7)	0.0258 (9)	0.0176 (8)	0.0006 (6)	−0.0010 (6)	0.0005 (6)
C1	0.0138 (9)	0.0494 (14)	0.0247 (11)	−0.0010 (8)	−0.0004 (8)	0.0007 (9)
C2	0.0154 (8)	0.0191 (9)	0.0178 (9)	−0.0018 (7)	−0.0006 (7)	0.0024 (7)
C3	0.0190 (9)	0.0317 (11)	0.0139 (9)	−0.0002 (7)	0.0024 (7)	−0.0020 (7)
C4	0.0145 (8)	0.0304 (11)	0.0195 (10)	−0.0004 (7)	0.0049 (7)	0.0000 (8)
C5	0.0147 (8)	0.0158 (9)	0.0179 (9)	−0.0008 (6)	0.0008 (7)	0.0011 (7)
C6	0.0198 (8)	0.0208 (10)	0.0127 (9)	−0.0015 (7)	0.0027 (7)	−0.0006 (7)
C7	0.0144 (8)	0.0223 (10)	0.0189 (9)	0.0009 (7)	0.0057 (7)	0.0007 (7)
C8	0.0155 (8)	0.0160 (9)	0.0168 (9)	−0.0012 (6)	0.0013 (7)	0.0014 (7)
C9	0.0172 (8)	0.0173 (9)	0.0179 (9)	0.0000 (7)	0.0027 (7)	0.0001 (7)
C10	0.0173 (8)	0.0174 (9)	0.0153 (9)	−0.0010 (7)	0.0000 (7)	0.0002 (7)
C11	0.0193 (9)	0.0161 (9)	0.0196 (10)	−0.0014 (7)	0.0000 (7)	0.0015 (7)
C12	0.0225 (9)	0.0291 (11)	0.0161 (9)	−0.0032 (8)	−0.0033 (7)	−0.0001 (7)
C13	0.0281 (10)	0.0385 (13)	0.0198 (10)	−0.0039 (9)	−0.0004 (8)	−0.0006 (8)
C14	0.0146 (8)	0.0282 (11)	0.0231 (10)	0.0038 (7)	0.0011 (7)	−0.0027 (8)
C15	0.0181 (9)	0.0363 (12)	0.0185 (10)	0.0004 (8)	0.0037 (8)	−0.0050 (8)

Br1—C15	1.9581 (19)	C5—C8	1.474 (2)
O1—C2	1.3746 (18)	C6—C7	1.394 (2)
O1—C1	1.431 (2)	C6—H6	0.9500
O2—C11	1.2103 (19)	C7—H7	0.9500
O3—C11	1.341 (2)	C8—C9	1.406 (2)
O3—C12	1.456 (2)	C9—C10	1.375 (2)
N1—C8	1.343 (2)	C9—H9	0.9500
N1—N2	1.3515 (18)	C10—C11	1.480 (2)
N2—C10	1.366 (2)	C12—C13	1.505 (2)
N2—C14	1.459 (2)	C12—H12A	0.9900
C1—H1A	0.9800	C12—H12B	0.9900
C1—H1B	0.9800	C13—H13A	0.9800
C1—H1C	0.9800	C13—H13B	0.9800
C2—C3	1.384 (2)	C13—H13C	0.9800
C2—C7	1.389 (2)	C14—C15	1.511 (2)
C3—C4	1.383 (2)	C14—H14A	0.9900
C3—H3	0.9500	C14—H14B	0.9900
C4—C5	1.396 (2)	C15—H15A	0.9900
C4—H4	0.9500	C15—H15B	0.9900
C5—C6	1.386 (2)
C2—O1—C1	116.96 (13)	C10—C9—C8	105.49 (15)
C11—O3—C12	116.03 (13)	C10—C9—H9	127.3
C8—N1—N2	105.62 (13)	C8—C9—H9	127.3
N1—N2—C10	111.51 (13)	N2—C10—C9	106.80 (14)
N1—N2—C14	117.78 (13)	N2—C10—C11	123.97 (15)
C10—N2—C14	130.28 (14)	C9—C10—C11	129.22 (16)
O1—C1—H1A	109.5	O2—C11—O3	124.45 (16)
O1—C1—H1B	109.5	O2—C11—C10	126.26 (17)
H1A—C1—H1B	109.5	O3—C11—C10	109.29 (14)
O1—C1—H1C	109.5	O3—C12—C13	106.78 (14)
H1A—C1—H1C	109.5	O3—C12—H12A	110.4
H1B—C1—H1C	109.5	C13—C12—H12A	110.4
O1—C2—C3	115.67 (15)	O3—C12—H12B	110.4
O1—C2—C7	124.70 (15)	C13—C12—H12B	110.4
C3—C2—C7	119.63 (15)	H12A—C12—H12B	108.6
C4—C3—C2	120.12 (16)	C12—C13—H13A	109.5
C4—C3—H3	119.9	C12—C13—H13B	109.5
C2—C3—H3	119.9	H13A—C13—H13B	109.5
C3—C4—C5	121.41 (16)	C12—C13—H13C	109.5
C3—C4—H4	119.3	H13A—C13—H13C	109.5
C5—C4—H4	119.3	H13B—C13—H13C	109.5
C6—C5—C4	117.70 (15)	N2—C14—C15	112.65 (15)
C6—C5—C8	122.05 (15)	N2—C14—H14A	109.1
C4—C5—C8	120.25 (15)	C15—C14—H14A	109.1
C5—C6—C7	121.58 (16)	N2—C14—H14B	109.1
C5—C6—H6	119.2	C15—C14—H14B	109.1
C7—C6—H6	119.2	H14A—C14—H14B	107.8
C2—C7—C6	119.56 (15)	C14—C15—Br1	111.80 (12)
C2—C7—H7	120.2	C14—C15—H15A	109.3
C6—C7—H7	120.2	Br1—C15—H15A	109.3
N1—C8—C9	110.58 (15)	C14—C15—H15B	109.3
N1—C8—C5	120.26 (15)	Br1—C15—H15B	109.3
C9—C8—C5	129.14 (15)	H15A—C15—H15B	107.9
C8—N1—N2—C10	−1.04 (18)	C4—C5—C8—C9	−175.81 (17)
C8—N1—N2—C14	−174.27 (15)	N1—C8—C9—C10	−0.5 (2)
C1—O1—C2—C3	−179.24 (16)	C5—C8—C9—C10	−178.89 (16)
C1—O1—C2—C7	1.2 (2)	N1—N2—C10—C9	0.77 (19)
O1—C2—C3—C4	−179.36 (16)	C14—N2—C10—C9	172.91 (17)
C7—C2—C3—C4	0.2 (3)	N1—N2—C10—C11	−178.04 (15)
C2—C3—C4—C5	0.3 (3)	C14—N2—C10—C11	−5.9 (3)
C3—C4—C5—C6	−0.4 (3)	C8—C9—C10—N2	−0.18 (19)
C3—C4—C5—C8	−179.62 (16)	C8—C9—C10—C11	178.54 (17)
C4—C5—C6—C7	−0.1 (3)	C12—O3—C11—O2	3.3 (2)
C8—C5—C6—C7	179.16 (16)	C12—O3—C11—C10	−176.61 (14)
O1—C2—C7—C6	178.88 (15)	N2—C10—C11—O2	−7.2 (3)
C3—C2—C7—C6	−0.6 (3)	C9—C10—C11—O2	174.33 (19)
C5—C6—C7—C2	0.6 (3)	N2—C10—C11—O3	172.76 (16)
N2—N1—C8—C9	0.91 (19)	C9—C10—C11—O3	−5.8 (2)
N2—N1—C8—C5	179.50 (14)	C11—O3—C12—C13	176.44 (15)
C6—C5—C8—N1	−173.34 (16)	N1—N2—C14—C15	−64.7 (2)
C4—C5—C8—N1	5.9 (2)	C10—N2—C14—C15	123.56 (19)
C6—C5—C8—C9	5.0 (3)	N2—C14—C15—Br1	−67.21 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Br1i	0.95	2.93	3.6791 (18)	137
C15—H15B···O1ii	0.99	2.56	3.288 (2)	130

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Br1i	0.95	2.93	3.6791 (18)	137
C15—H15B⋯O1ii	0.99	2.56	3.288 (2)	130

Symmetry codes: (i) ; (ii) .