(2E)-1-(4-Bromo-phen-yl)-3-[3-(4-meth-oxy-phen-yl)-1-phenyl-1H-pyrazol-4-yl]prop-2-en-1-one.

The pyrazole ring in the title compound, C25H19BrN2O2, is almost planar (r.m.s. deviation = 0.003 Å) and forms dihedral angles of 7.56 (13) and 56.48 (13)° with the N- and C-bound benzene rings, respectively. The prop-2-en-1-one residue has an E conformation about the C=C double bond [1.328 (4) Å] and is almost coplanar with the pyrazole ring [C-C-C-C torsion angle = -174.4 (3)°]. A twist between the prop-2-en-1-one unit and the terminal benzene ring is evident [C-C-C-C torsion angle = -15.4 (4)°]. In the crystal, mol-ecules are consolidated into a three-dimensional architecture by C-H⋯O, C-H⋯π and π-π [centroid-centroid separation = 3.7597 (16) Å] inter-actions.

Related literature

For background details and biological applications of pyrazole and chalcones, see: Babasaheb et al. (2009 ▶); Prasath & Bhavana (2012 ▶); Prasath et al. (2013 ▶). For the structure of the 4-meth­oxy­phenyl pyrazole compound, see: Fun et al. (2011 ▶).

Experimental

Crystal data

C25H19BrN2O2

M = 459.33

Triclinic,

a = 7.3643 (3) Å

b = 10.6795 (5) Å

c = 13.1038 (6) Å

α = 91.822 (4)°

β = 101.311 (4)°

γ = 91.792 (3)°

V = 1009.31 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.06 mm−1

T = 100 K

0.50 × 0.40 × 0.30 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013 ▶) T min = 0.921, T max = 1.000

8736 measured reflections

4649 independent reflections

3875 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.111

S = 1.04

4649 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrysAlis PRO (Agilent, 2013 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016838/hb7095sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016838/hb7095Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813016838/hb7095Isup3.cml

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

C25H19BrN2O2	Z = 2
Mr = 459.33	F(000) = 468
Triclinic, P1	Dx = 1.511 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3643 (3) Å	Cell parameters from 2849 reflections
b = 10.6795 (5) Å	θ = 3.0–27.5°
c = 13.1038 (6) Å	µ = 2.06 mm−1
α = 91.822 (4)°	T = 100 K
β = 101.311 (4)°	Prism, yellow
γ = 91.792 (3)°	0.50 × 0.40 × 0.30 mm
V = 1009.31 (8) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	4649 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3875 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 3.0°
ω scan	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2013)	k = −13→13
Tmin = 0.921, Tmax = 1.000	l = −15→17
8736 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0485P)2 + 0.731P] where P = (Fo2 + 2Fc2)/3
4649 reflections	(Δ/σ)max = 0.001
271 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.55 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	0.11696 (4)	1.12761 (3)	0.86611 (2)	0.03080 (12)
O1	0.6500 (3)	0.61824 (19)	0.97288 (15)	0.0248 (4)
O2	0.6830 (2)	0.98810 (16)	0.42732 (14)	0.0185 (4)
N1	1.2201 (3)	0.58644 (19)	0.65301 (17)	0.0145 (4)
N2	1.3006 (3)	0.51261 (19)	0.73128 (16)	0.0137 (4)
C1	0.5191 (4)	0.7966 (2)	0.8896 (2)	0.0172 (5)
C2	0.5417 (4)	0.8979 (3)	0.8283 (2)	0.0213 (6)
H2	0.6396	0.8992	0.7906	0.026*
C3	0.4235 (4)	0.9967 (3)	0.8216 (2)	0.0227 (6)
H3	0.4391	1.0656	0.7796	0.027*
C4	0.2828 (4)	0.9933 (3)	0.8769 (2)	0.0208 (6)
C5	0.2543 (4)	0.8941 (3)	0.9378 (2)	0.0227 (6)
H5	0.1551	0.8931	0.9745	0.027*
C6	0.3751 (4)	0.7954 (3)	0.9440 (2)	0.0205 (6)
H6	0.3587	0.7266	0.9859	0.025*
C7	0.6504 (4)	0.6906 (2)	0.9023 (2)	0.0173 (5)
C8	0.7763 (4)	0.6782 (2)	0.8287 (2)	0.0176 (5)
H8	0.7483	0.7174	0.7637	0.021*
C9	0.9287 (4)	0.6129 (2)	0.8514 (2)	0.0164 (5)
H9	0.9515	0.5759	0.9174	0.020*
C10	1.0640 (3)	0.5920 (2)	0.7864 (2)	0.0147 (5)
C11	1.2115 (4)	0.5143 (2)	0.8117 (2)	0.0155 (5)
H11	1.2439	0.4703	0.8742	0.019*
C12	1.0770 (3)	0.6352 (2)	0.68607 (19)	0.0130 (5)
C13	1.4631 (3)	0.4466 (2)	0.7208 (2)	0.0142 (5)
C14	1.5469 (4)	0.4699 (2)	0.6376 (2)	0.0162 (5)
H14	1.4993	0.5305	0.5889	0.019*
C15	1.7022 (4)	0.4038 (2)	0.6258 (2)	0.0172 (5)
H15	1.7594	0.4183	0.5681	0.021*
C16	1.7731 (4)	0.3171 (2)	0.6979 (2)	0.0198 (6)
H16	1.8791	0.2722	0.6899	0.024*
C17	1.6886 (4)	0.2960 (3)	0.7821 (2)	0.0215 (6)
H17	1.7381	0.2370	0.8319	0.026*
C18	1.5322 (4)	0.3604 (2)	0.7942 (2)	0.0186 (5)
H18	1.4741	0.3457	0.8516	0.022*
C19	0.9641 (3)	0.7257 (2)	0.62029 (19)	0.0132 (5)
C20	0.9485 (3)	0.8468 (2)	0.6597 (2)	0.0153 (5)
H20	1.0031	0.8678	0.7303	0.018*
C21	0.8557 (3)	0.9374 (2)	0.5987 (2)	0.0153 (5)
H21	0.8458	1.0191	0.6274	0.018*
C22	0.7771 (3)	0.9074 (2)	0.4951 (2)	0.0141 (5)
C23	0.7907 (4)	0.7859 (2)	0.4545 (2)	0.0164 (5)
H23	0.7359	0.7648	0.3840	0.020*
C24	0.8836 (3)	0.6967 (2)	0.5167 (2)	0.0154 (5)
H24	0.8925	0.6146	0.4884	0.019*
C25	0.6747 (4)	1.1152 (2)	0.4644 (2)	0.0196 (6)
H25A	0.6039	1.1636	0.4089	0.029*
H25B	0.8006	1.1521	0.4851	0.029*
H25C	0.6138	1.1166	0.5245	0.029*

	U11	U22	U33	U12	U13	U23
Br1	0.02570 (17)	0.03300 (19)	0.03209 (19)	0.01428 (13)	0.00041 (12)	−0.00323 (13)
O1	0.0285 (11)	0.0290 (11)	0.0198 (10)	0.0076 (9)	0.0099 (9)	0.0081 (9)
O2	0.0181 (9)	0.0157 (9)	0.0203 (9)	0.0013 (7)	−0.0009 (8)	0.0053 (8)
N1	0.0168 (10)	0.0125 (10)	0.0143 (10)	0.0032 (8)	0.0026 (8)	0.0040 (8)
N2	0.0139 (10)	0.0133 (10)	0.0140 (10)	0.0025 (8)	0.0023 (8)	0.0037 (8)
C1	0.0174 (12)	0.0205 (13)	0.0129 (12)	0.0009 (11)	0.0018 (10)	−0.0020 (10)
C2	0.0200 (13)	0.0246 (14)	0.0206 (14)	0.0025 (11)	0.0065 (11)	0.0015 (12)
C3	0.0259 (14)	0.0216 (14)	0.0209 (14)	0.0038 (12)	0.0042 (12)	0.0041 (12)
C4	0.0177 (13)	0.0239 (14)	0.0185 (13)	0.0078 (11)	−0.0025 (11)	−0.0043 (11)
C5	0.0157 (13)	0.0336 (16)	0.0189 (14)	0.0042 (12)	0.0043 (11)	−0.0035 (12)
C6	0.0212 (13)	0.0268 (14)	0.0147 (13)	0.0023 (11)	0.0054 (11)	0.0038 (11)
C7	0.0172 (12)	0.0200 (13)	0.0144 (12)	−0.0010 (10)	0.0025 (10)	−0.0003 (11)
C8	0.0195 (13)	0.0189 (13)	0.0149 (12)	0.0006 (11)	0.0044 (10)	0.0007 (10)
C9	0.0192 (12)	0.0180 (12)	0.0124 (12)	0.0009 (10)	0.0034 (10)	0.0039 (10)
C10	0.0141 (12)	0.0149 (12)	0.0151 (12)	0.0014 (10)	0.0024 (10)	0.0015 (10)
C11	0.0170 (12)	0.0155 (12)	0.0144 (12)	0.0003 (10)	0.0032 (10)	0.0037 (10)
C12	0.0111 (11)	0.0113 (11)	0.0157 (12)	−0.0011 (9)	0.0013 (9)	−0.0006 (10)
C13	0.0139 (11)	0.0136 (11)	0.0144 (12)	0.0025 (10)	0.0009 (10)	0.0011 (10)
C14	0.0189 (12)	0.0140 (12)	0.0160 (12)	0.0025 (10)	0.0040 (10)	0.0016 (10)
C15	0.0174 (12)	0.0195 (13)	0.0158 (13)	−0.0001 (10)	0.0060 (10)	−0.0008 (10)
C16	0.0172 (12)	0.0191 (13)	0.0244 (14)	0.0043 (11)	0.0067 (11)	0.0013 (11)
C17	0.0231 (14)	0.0217 (14)	0.0210 (14)	0.0090 (11)	0.0053 (11)	0.0090 (11)
C18	0.0190 (13)	0.0186 (13)	0.0200 (13)	0.0036 (11)	0.0064 (11)	0.0073 (11)
C19	0.0109 (11)	0.0152 (12)	0.0142 (12)	0.0009 (9)	0.0034 (9)	0.0035 (10)
C20	0.0155 (12)	0.0185 (12)	0.0116 (12)	0.0004 (10)	0.0018 (10)	0.0013 (10)
C21	0.0145 (12)	0.0126 (12)	0.0190 (13)	0.0006 (10)	0.0046 (10)	−0.0011 (10)
C22	0.0088 (11)	0.0157 (12)	0.0185 (13)	−0.0015 (9)	0.0038 (10)	0.0059 (10)
C23	0.0176 (12)	0.0162 (12)	0.0139 (12)	−0.0009 (10)	0.0001 (10)	0.0002 (10)
C24	0.0165 (12)	0.0124 (11)	0.0172 (13)	−0.0013 (10)	0.0032 (10)	−0.0002 (10)
C25	0.0181 (13)	0.0154 (12)	0.0255 (14)	0.0025 (11)	0.0037 (11)	0.0076 (11)

Br1—C4	1.903 (3)	C11—H11	0.9500
O1—C7	1.224 (3)	C12—C19	1.480 (3)
O2—C22	1.362 (3)	C13—C14	1.379 (4)
O2—C25	1.434 (3)	C13—C18	1.388 (4)
N1—C12	1.329 (3)	C14—C15	1.394 (3)
N1—N2	1.366 (3)	C14—H14	0.9500
N2—C11	1.347 (3)	C15—C16	1.384 (4)
N2—C13	1.435 (3)	C15—H15	0.9500
C1—C6	1.389 (4)	C16—C17	1.389 (4)
C1—C2	1.393 (4)	C16—H16	0.9500
C1—C7	1.504 (4)	C17—C18	1.392 (4)
C2—C3	1.383 (4)	C17—H17	0.9500
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.376 (4)	C19—C20	1.394 (3)
C3—H3	0.9500	C19—C24	1.391 (3)
C4—C5	1.382 (4)	C20—C21	1.385 (4)
C5—C6	1.394 (4)	C20—H20	0.9500
C5—H5	0.9500	C21—C22	1.391 (4)
C6—H6	0.9500	C21—H21	0.9500
C7—C8	1.470 (4)	C22—C23	1.400 (3)
C8—C9	1.328 (4)	C23—C24	1.383 (4)
C8—H8	0.9500	C23—H23	0.9500
C9—C10	1.450 (3)	C24—H24	0.9500
C9—H9	0.9500	C25—H25A	0.9800
C10—C11	1.382 (3)	C25—H25B	0.9800
C10—C12	1.427 (3)	C25—H25C	0.9800
C22—O2—C25	117.2 (2)	C14—C13—N2	119.2 (2)
C12—N1—N2	105.0 (2)	C18—C13—N2	119.4 (2)
C11—N2—N1	112.2 (2)	C13—C14—C15	119.4 (2)
C11—N2—C13	128.4 (2)	C13—C14—H14	120.3
N1—N2—C13	119.4 (2)	C15—C14—H14	120.3
C6—C1—C2	119.1 (2)	C16—C15—C14	120.2 (2)
C6—C1—C7	118.7 (2)	C16—C15—H15	119.9
C2—C1—C7	122.1 (2)	C14—C15—H15	119.9
C3—C2—C1	120.8 (3)	C15—C16—C17	119.7 (2)
C3—C2—H2	119.6	C15—C16—H16	120.1
C1—C2—H2	119.6	C17—C16—H16	120.1
C4—C3—C2	118.7 (3)	C16—C17—C18	120.7 (3)
C4—C3—H3	120.6	C16—C17—H17	119.7
C2—C3—H3	120.6	C18—C17—H17	119.7
C3—C4—C5	122.3 (2)	C13—C18—C17	118.6 (2)
C3—C4—Br1	118.9 (2)	C13—C18—H18	120.7
C5—C4—Br1	118.7 (2)	C17—C18—H18	120.7
C4—C5—C6	118.2 (2)	C20—C19—C24	118.3 (2)
C4—C5—H5	120.9	C20—C19—C12	119.7 (2)
C6—C5—H5	120.9	C24—C19—C12	121.8 (2)
C1—C6—C5	120.8 (3)	C21—C20—C19	121.8 (2)
C1—C6—H6	119.6	C21—C20—H20	119.1
C5—C6—H6	119.6	C19—C20—H20	119.1
O1—C7—C8	122.2 (2)	C20—C21—C22	119.3 (2)
O1—C7—C1	119.7 (2)	C20—C21—H21	120.3
C8—C7—C1	118.1 (2)	C22—C21—H21	120.3
C9—C8—C7	121.1 (2)	O2—C22—C21	124.8 (2)
C9—C8—H8	119.4	O2—C22—C23	115.6 (2)
C7—C8—H8	119.4	C21—C22—C23	119.6 (2)
C8—C9—C10	127.1 (2)	C24—C23—C22	120.2 (2)
C8—C9—H9	116.4	C24—C23—H23	119.9
C10—C9—H9	116.4	C22—C23—H23	119.9
C11—C10—C12	104.5 (2)	C23—C24—C19	120.8 (2)
C11—C10—C9	123.8 (2)	C23—C24—H24	119.6
C12—C10—C9	131.6 (2)	C19—C24—H24	119.6
N2—C11—C10	107.2 (2)	O2—C25—H25A	109.5
N2—C11—H11	126.4	O2—C25—H25B	109.5
C10—C11—H11	126.4	H25A—C25—H25B	109.5
N1—C12—C10	111.1 (2)	O2—C25—H25C	109.5
N1—C12—C19	118.7 (2)	H25A—C25—H25C	109.5
C10—C12—C19	130.2 (2)	H25B—C25—H25C	109.5
C14—C13—C18	121.4 (2)
C12—N1—N2—C11	0.0 (3)	C9—C10—C12—C19	6.5 (5)
C12—N1—N2—C13	−179.2 (2)	C11—N2—C13—C14	−171.7 (2)
C6—C1—C2—C3	0.3 (4)	N1—N2—C13—C14	7.3 (3)
C7—C1—C2—C3	−177.2 (2)	C11—N2—C13—C18	8.5 (4)
C1—C2—C3—C4	0.2 (4)	N1—N2—C13—C18	−172.5 (2)
C2—C3—C4—C5	−0.8 (4)	C18—C13—C14—C15	1.4 (4)
C2—C3—C4—Br1	−178.9 (2)	N2—C13—C14—C15	−178.5 (2)
C3—C4—C5—C6	1.0 (4)	C13—C14—C15—C16	−1.1 (4)
Br1—C4—C5—C6	179.1 (2)	C14—C15—C16—C17	0.2 (4)
C2—C1—C6—C5	−0.1 (4)	C15—C16—C17—C18	0.6 (4)
C7—C1—C6—C5	177.5 (2)	C14—C13—C18—C17	−0.6 (4)
C4—C5—C6—C1	−0.5 (4)	N2—C13—C18—C17	179.2 (2)
C6—C1—C7—O1	−13.0 (4)	C16—C17—C18—C13	−0.3 (4)
C2—C1—C7—O1	164.4 (3)	N1—C12—C19—C20	−120.3 (3)
C6—C1—C7—C8	167.2 (2)	C10—C12—C19—C20	56.7 (4)
C2—C1—C7—C8	−15.4 (4)	N1—C12—C19—C24	54.7 (3)
O1—C7—C8—C9	−19.6 (4)	C10—C12—C19—C24	−128.3 (3)
C1—C7—C8—C9	160.2 (2)	C24—C19—C20—C21	0.1 (4)
C7—C8—C9—C10	179.5 (2)	C12—C19—C20—C21	175.2 (2)
C8—C9—C10—C11	−174.4 (3)	C19—C20—C21—C22	−0.6 (4)
C8—C9—C10—C12	1.9 (5)	C25—O2—C22—C21	4.0 (4)
N1—N2—C11—C10	0.3 (3)	C25—O2—C22—C23	−176.8 (2)
C13—N2—C11—C10	179.4 (2)	C20—C21—C22—O2	−179.9 (2)
C12—C10—C11—N2	−0.5 (3)	C20—C21—C22—C23	0.9 (4)
C9—C10—C11—N2	176.7 (2)	O2—C22—C23—C24	179.9 (2)
N2—N1—C12—C10	−0.3 (3)	C21—C22—C23—C24	−0.8 (4)
N2—N1—C12—C19	177.2 (2)	C22—C23—C24—C19	0.3 (4)
C11—C10—C12—N1	0.5 (3)	C20—C19—C24—C23	0.1 (4)
C9—C10—C12—N1	−176.3 (3)	C12—C19—C24—C23	−175.0 (2)
C11—C10—C12—C19	−176.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.95	2.25	3.198 (3)	173
C25—H25B···Cg1ii	0.98	2.61	3.478 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.95	2.25	3.198 (3)	173
C25—H25B⋯Cg1ii	0.98	2.61	3.478 (3)	148

Symmetry codes: (i) ; (ii) .