(2Z)-3-(3-Bromo­anilino)-1-(5-hy­droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

Asiri, A.M.; Faidallah, H.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006939

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o813

doi:10.1107/S1600536812006939

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(2Z)-3-(3-Bromoanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

Abdullah M. Asiri,^a,^b ‡ Hassan M. Faidallah,^a Seik Weng Ng ^c and Edward R. T. Tiekink ^c ^*

^aChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah, Saudi Arabia, ^bThe Center of Excellence for Advanced Materials Research, King Abdulaziz University, Jeddah, PO Box 80203, Saudi Arabia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 15 February 2012; accepted 16 February 2012; online 24 February 2012)

In the title compound, C₂₀H₁₈BrN₃O₂, the central carbonyl group forms amine-N—H⋯O and hydroxy-O—H⋯O hydrogen bonds, which lead to two fused S(6) rings. The N-bound phenyl ring is coplanar with the five-membered ring to which it is attached [dihedral angle = 5.22 (18)°], but the dihedral angle [33.87 (17)°] between the terminal phenyl and bromobenzene rings indicates an overall twist in the molecule. In the crystal packing, molecules assemble into dimeric aggregates via C—H⋯π interactions.

Related literature

For background to the synthesis, see: Gelin et al. (1983 ); Bendaas et al. (1999 ). For the structures of the 4-chloro and 4-methoxy derivatives, see: Asiri, Al-Youbi, Alamry et al. (2011 ); Asiri, Al-Youbi, Faidallah et al. (2011 ).

Experimental

Crystal data

C₂₀H₁₈BrN₃O₂
M_r = 412.28
Monoclinic, P 2₁ /c
a = 8.7065 (5) Å
b = 11.7982 (8) Å
c = 17.5954 (12) Å
β = 101.536 (6)°
V = 1770.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 2.34 mm⁻¹
T = 100 K
0.25 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.592, T_max = 0.892
7812 measured reflections
4041 independent reflections
3033 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.105
S = 1.01
4041 reflections
245 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.58 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.84 (1)	1.68 (3)	2.468 (3)	154 (6)
N3—H3⋯O2	0.88 (1)	1.87 (3)	2.617 (4)	142 (4)
C14—H14B⋯Cg1ⁱ	0.98	2.69	3.495 (4)	140
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006939/sj5199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006939/sj5199Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006939/sj5199Isup3.cml

checkCIF report

Comment top

The title compound, 3-(3-bromoanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one (I), was synthesized during investigations of reactions between pyrazoles and aniline derivatives based on literature precedents (Gelin et al., 1983; Bendaas et al., 1999) and was one of several compounds that were isolated in crystalline form (Asiri, Al-Youbi, Alamry et al., 2011; Asiri, Al-Youbi, Faidallah et al., 2011). As a continuation of these structural studies, the analysis of (I) is now described.

In (I), Fig. 1, The configuration about the formal C12═C13 bond [1.376 (4) Å] is Z. This arrangement allows the central O2-carbonyl atom to accept two hydrogen bonds from the adjacent hydroxyl and amine groups to close a pair of fused S(6) rings, Table 1. While the N-bound phenyl ring is co-planar with the five-membered ring to which it is connected, forming a dihedral angle of 5.22 (18)°, a twist in the molecule is evident as seen in the dihedral angle formed between the terminal phenyl and bromobenzene rings, dihedral angle = 33.87 (17)°.

The most notable feature of the crystal packing is the formation of C—H···π interactions where the π-system is the five-membered ring, Table 1. The resulting dimeric aggregates assemble into zigzag layers in the bc plane and stack along the a axis, Fig. 2.

Related literature top

For background to the synthesis, see: Gelin et al. (1983); Bendaas et al. (1999). For the structures of the 4-chloro and 4-methoxy derivatives, see: Asiri, Al-Youbi, Alamry et al. (2011); Asiri, Al-Youbi, Faidallah et al. (2011).

Experimental top

A solution of 4-acetoacetyl-5-hydroxy-3-methyl-1-phenylpyrazole (0.005 mol) and 3-bromo-aniline (0.005 mol) in ethanol (25 ml) was refluxed for 2 h. The precipitate obtained from the hot solution was collected washed with methanol and recrystallized from its ethanol-benzene solution to provide yellow crystals; M.pt: 412–413 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); 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).

Figures top

	Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the c axis of the unit-cell contents of (I). The C—H···π interactions are shown as purple dashed lines.

(2Z)-3-(3-Bromoanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H- pyrazol-4-yl)but-2-en-1-one top

Crystal data top

C₂₀H₁₈BrN₃O₂	F(000) = 840
M_r = 412.28	D_x = 1.546 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1846 reflections
a = 8.7065 (5) Å	θ = 2.4–27.5°
b = 11.7982 (8) Å	µ = 2.34 mm⁻¹
c = 17.5954 (12) Å	T = 100 K
β = 101.536 (6)°	Bead, yellow
V = 1770.9 (2) Å³	0.25 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4041 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3033 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.048
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −10→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→14
T_min = 0.592, T_max = 0.892	l = −14→22
7812 measured reflections

Refinement top

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0373P)²] where P = (F_o² + 2F_c²)/3
4041 reflections	(Δ/σ)_max = 0.001
245 parameters	Δρ_max = 0.58 e Å⁻³
2 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₀H₁₈BrN₃O₂	V = 1770.9 (2) Å³
M_r = 412.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7065 (5) Å	µ = 2.34 mm⁻¹
b = 11.7982 (8) Å	T = 100 K
c = 17.5954 (12) Å	0.25 × 0.10 × 0.05 mm
β = 101.536 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4041 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3033 reflections with I > 2σ(I)
T_min = 0.592, T_max = 0.892	R_int = 0.048
7812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	2 restraints
wR(F²) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.58 e Å⁻³
4041 reflections	Δρ_min = −0.47 e Å⁻³
245 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Br1	−0.18793 (4)	0.67333 (3)	0.911231 (19)	0.01841 (12)
O1	0.4430 (3)	0.3220 (2)	0.53800 (14)	0.0156 (5)
H1	0.409 (7)	0.351 (5)	0.575 (2)	0.11 (2)*
O2	0.3101 (2)	0.44759 (19)	0.61666 (13)	0.0160 (5)
N1	0.3917 (3)	0.3741 (2)	0.40520 (15)	0.0126 (6)
N2	0.3061 (3)	0.4591 (2)	0.35913 (16)	0.0148 (6)
N3	0.1528 (3)	0.5638 (2)	0.70229 (17)	0.0160 (6)
H3	0.218 (3)	0.510 (2)	0.694 (2)	0.034 (12)*
C1	0.4707 (3)	0.2917 (3)	0.36862 (19)	0.0142 (7)
C2	0.4743 (4)	0.3022 (3)	0.2904 (2)	0.0174 (7)
H2	0.4249	0.3651	0.2617	0.021*
C3	0.5495 (4)	0.2218 (3)	0.2542 (2)	0.0205 (8)
H3A	0.5514	0.2293	0.2006	0.025*
C4	0.6222 (4)	0.1298 (3)	0.2955 (2)	0.0190 (8)
H4	0.6733	0.0740	0.2705	0.023*
C5	0.6196 (4)	0.1204 (3)	0.3735 (2)	0.0197 (8)
H5	0.6701	0.0578	0.4019	0.024*
C6	0.5448 (4)	0.2005 (3)	0.4112 (2)	0.0176 (7)
H6	0.5442	0.1932	0.4649	0.021*
C7	0.3772 (3)	0.3860 (3)	0.48029 (19)	0.0131 (7)
C8	0.2809 (3)	0.4804 (3)	0.48482 (19)	0.0129 (7)
C9	0.2418 (3)	0.5222 (3)	0.40686 (18)	0.0130 (7)
C10	0.1464 (4)	0.6231 (3)	0.37541 (19)	0.0184 (7)
H10A	0.1370	0.6263	0.3190	0.028*
H10B	0.1978	0.6922	0.3989	0.028*
H10C	0.0418	0.6172	0.3877	0.028*
C11	0.2435 (3)	0.5109 (3)	0.55732 (19)	0.0155 (7)
C12	0.1439 (3)	0.6012 (3)	0.56902 (19)	0.0154 (7)
H12	0.1024	0.6472	0.5254	0.018*
C13	0.1018 (3)	0.6283 (3)	0.63815 (19)	0.0152 (7)
C14	0.0010 (4)	0.7306 (3)	0.6434 (2)	0.0178 (7)
H14A	0.0427	0.7721	0.6914	0.027*
H14B	−0.1065	0.7062	0.6435	0.027*
H14C	0.0014	0.7801	0.5987	0.027*
C15	0.1320 (4)	0.5704 (3)	0.77953 (19)	0.0165 (7)
C16	0.2537 (4)	0.5276 (3)	0.8356 (2)	0.0242 (8)
H16	0.3453	0.4987	0.8208	0.029*
C17	0.2420 (4)	0.5269 (3)	0.9128 (2)	0.0256 (9)
H17	0.3254	0.4963	0.9504	0.031*
C18	0.1116 (4)	0.5696 (3)	0.9364 (2)	0.0220 (8)
H18	0.1046	0.5707	0.9896	0.026*
C19	−0.0089 (4)	0.6110 (3)	0.87941 (19)	0.0154 (7)
C20	−0.0032 (4)	0.6109 (3)	0.80153 (19)	0.0172 (7)
H20	−0.0893	0.6377	0.7639	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01953 (19)	0.0200 (2)	0.01736 (19)	0.00189 (14)	0.00775 (13)	−0.00017 (14)
O1	0.0169 (11)	0.0183 (13)	0.0119 (12)	0.0042 (10)	0.0035 (9)	0.0031 (10)
O2	0.0196 (11)	0.0165 (12)	0.0120 (12)	0.0033 (10)	0.0034 (9)	−0.0002 (10)
N1	0.0147 (13)	0.0130 (14)	0.0110 (14)	0.0010 (11)	0.0043 (10)	0.0009 (11)
N2	0.0159 (13)	0.0132 (14)	0.0150 (15)	0.0020 (12)	0.0024 (11)	0.0021 (12)
N3	0.0175 (14)	0.0164 (16)	0.0154 (15)	0.0035 (13)	0.0069 (11)	0.0011 (13)
C1	0.0119 (15)	0.0175 (17)	0.0134 (17)	−0.0035 (14)	0.0028 (12)	−0.0040 (14)
C2	0.0162 (16)	0.0213 (19)	0.0148 (18)	−0.0002 (15)	0.0032 (13)	−0.0013 (15)
C3	0.0192 (17)	0.027 (2)	0.0165 (19)	−0.0036 (16)	0.0072 (14)	−0.0036 (16)
C4	0.0150 (16)	0.0172 (18)	0.026 (2)	−0.0022 (15)	0.0072 (14)	−0.0088 (15)
C5	0.0193 (17)	0.0179 (19)	0.022 (2)	0.0018 (15)	0.0036 (14)	−0.0020 (16)
C6	0.0152 (16)	0.0216 (19)	0.0167 (18)	−0.0043 (15)	0.0046 (13)	−0.0020 (15)
C7	0.0141 (15)	0.0160 (17)	0.0097 (16)	−0.0028 (14)	0.0034 (12)	0.0004 (14)
C8	0.0117 (15)	0.0145 (17)	0.0121 (17)	−0.0026 (14)	0.0016 (12)	0.0014 (14)
C9	0.0140 (15)	0.0129 (17)	0.0123 (17)	−0.0014 (14)	0.0031 (12)	0.0016 (14)
C10	0.0221 (17)	0.0194 (19)	0.0146 (18)	0.0035 (15)	0.0055 (14)	−0.0007 (15)
C11	0.0127 (15)	0.0188 (18)	0.0150 (18)	−0.0068 (14)	0.0031 (13)	0.0007 (14)
C12	0.0147 (15)	0.0198 (18)	0.0117 (17)	−0.0013 (14)	0.0028 (12)	0.0017 (14)
C13	0.0129 (15)	0.0164 (18)	0.0163 (18)	−0.0049 (14)	0.0026 (13)	0.0000 (14)
C14	0.0201 (17)	0.0186 (19)	0.0151 (18)	−0.0006 (15)	0.0043 (13)	−0.0016 (14)
C15	0.0205 (16)	0.0162 (18)	0.0136 (18)	−0.0024 (15)	0.0051 (13)	−0.0002 (14)
C16	0.0202 (17)	0.033 (2)	0.020 (2)	0.0076 (17)	0.0049 (14)	0.0007 (17)
C17	0.0235 (18)	0.036 (2)	0.0172 (19)	0.0091 (17)	0.0031 (14)	0.0048 (17)
C18	0.0273 (18)	0.026 (2)	0.0129 (18)	−0.0004 (16)	0.0039 (14)	0.0031 (15)
C19	0.0177 (16)	0.0133 (18)	0.0174 (18)	0.0001 (14)	0.0090 (13)	0.0004 (14)
C20	0.0165 (16)	0.0220 (19)	0.0129 (17)	−0.0016 (15)	0.0025 (13)	−0.0009 (15)

Geometric parameters (Å, º) top

Br1—C19	1.906 (3)	C8—C11	1.425 (4)
O1—C7	1.303 (4)	C8—C9	1.433 (4)
O1—H1	0.843 (10)	C9—C10	1.493 (4)
O2—C11	1.320 (4)	C10—H10A	0.9800
N1—C7	1.359 (4)	C10—H10B	0.9800
N1—N2	1.406 (4)	C10—H10C	0.9800
N1—C1	1.417 (4)	C11—C12	1.415 (5)
N2—C9	1.327 (4)	C12—C13	1.376 (4)
N3—C13	1.360 (4)	C12—H12	0.9500
N3—C15	1.409 (4)	C13—C14	1.506 (5)
N3—H3	0.881 (10)	C14—H14A	0.9800
C1—C2	1.389 (4)	C14—H14B	0.9800
C1—C6	1.395 (5)	C14—H14C	0.9800
C2—C3	1.379 (5)	C15—C16	1.391 (4)
C2—H2	0.9500	C15—C20	1.395 (5)
C3—C4	1.386 (5)	C16—C17	1.382 (5)
C3—H3A	0.9500	C16—H16	0.9500
C4—C5	1.381 (5)	C17—C18	1.380 (5)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.389 (5)	C18—C19	1.387 (4)
C5—H5	0.9500	C18—H18	0.9500
C6—H6	0.9500	C19—C20	1.381 (4)
C7—C8	1.405 (4)	C20—H20	0.9500

C7—O1—H1	102 (4)	H10A—C10—H10B	109.5
C7—N1—N2	110.2 (3)	C9—C10—H10C	109.5
C7—N1—C1	131.3 (3)	H10A—C10—H10C	109.5
N2—N1—C1	118.5 (3)	H10B—C10—H10C	109.5
C9—N2—N1	106.1 (3)	O2—C11—C12	119.7 (3)
C13—N3—C15	133.3 (3)	O2—C11—C8	115.0 (3)
C13—N3—H3	113 (3)	C12—C11—C8	125.3 (3)
C15—N3—H3	114 (3)	C13—C12—C11	125.6 (3)
C2—C1—C6	120.1 (3)	C13—C12—H12	117.2
C2—C1—N1	119.9 (3)	C11—C12—H12	117.2
C6—C1—N1	120.0 (3)	N3—C13—C12	120.2 (3)
C3—C2—C1	120.2 (3)	N3—C13—C14	119.7 (3)
C3—C2—H2	119.9	C12—C13—C14	120.1 (3)
C1—C2—H2	119.9	C13—C14—H14A	109.5
C2—C3—C4	120.4 (3)	C13—C14—H14B	109.5
C2—C3—H3A	119.8	H14A—C14—H14B	109.5
C4—C3—H3A	119.8	C13—C14—H14C	109.5
C5—C4—C3	119.2 (3)	H14A—C14—H14C	109.5
C5—C4—H4	120.4	H14B—C14—H14C	109.5
C3—C4—H4	120.4	C16—C15—C20	119.5 (3)
C4—C5—C6	121.6 (3)	C16—C15—N3	115.9 (3)
C4—C5—H5	119.2	C20—C15—N3	124.4 (3)
C6—C5—H5	119.2	C17—C16—C15	120.2 (3)
C5—C6—C1	118.6 (3)	C17—C16—H16	119.9
C5—C6—H6	120.7	C15—C16—H16	119.9
C1—C6—H6	120.7	C18—C17—C16	121.4 (3)
O1—C7—N1	125.9 (3)	C18—C17—H17	119.3
O1—C7—C8	126.1 (3)	C16—C17—H17	119.3
N1—C7—C8	108.0 (3)	C17—C18—C19	117.4 (3)
C7—C8—C11	119.8 (3)	C17—C18—H18	121.3
C7—C8—C9	104.4 (3)	C19—C18—H18	121.3
C11—C8—C9	135.8 (3)	C20—C19—C18	123.0 (3)
N2—C9—C8	111.3 (3)	C20—C19—Br1	119.0 (2)
N2—C9—C10	119.1 (3)	C18—C19—Br1	117.9 (3)
C8—C9—C10	129.6 (3)	C19—C20—C15	118.4 (3)
C9—C10—H10A	109.5	C19—C20—H20	120.8
C9—C10—H10B	109.5	C15—C20—H20	120.8

C7—N1—N2—C9	0.6 (3)	C11—C8—C9—N2	−178.1 (3)
C1—N1—N2—C9	178.5 (3)	C7—C8—C9—C10	−178.0 (3)
C7—N1—C1—C2	−176.6 (3)	C11—C8—C9—C10	3.2 (6)
N2—N1—C1—C2	5.9 (4)	C7—C8—C11—O2	2.5 (4)
C7—N1—C1—C6	3.2 (5)	C9—C8—C11—O2	−178.9 (3)
N2—N1—C1—C6	−174.2 (3)	C7—C8—C11—C12	−177.7 (3)
C6—C1—C2—C3	0.9 (5)	C9—C8—C11—C12	1.0 (6)
N1—C1—C2—C3	−179.3 (3)	O2—C11—C12—C13	−3.1 (5)
C1—C2—C3—C4	−0.1 (5)	C8—C11—C12—C13	177.0 (3)
C2—C3—C4—C5	−0.5 (5)	C15—N3—C13—C12	179.1 (3)
C3—C4—C5—C6	0.5 (5)	C15—N3—C13—C14	0.0 (5)
C4—C5—C6—C1	0.3 (5)	C11—C12—C13—N3	−2.1 (5)
C2—C1—C6—C5	−0.9 (5)	C11—C12—C13—C14	176.9 (3)
N1—C1—C6—C5	179.2 (3)	C13—N3—C15—C16	−150.3 (3)
N2—N1—C7—O1	−179.2 (3)	C13—N3—C15—C20	33.1 (5)
C1—N1—C7—O1	3.2 (5)	C20—C15—C16—C17	−1.1 (5)
N2—N1—C7—C8	−0.2 (3)	N3—C15—C16—C17	−177.9 (3)
C1—N1—C7—C8	−177.8 (3)	C15—C16—C17—C18	−0.9 (6)
O1—C7—C8—C11	−2.2 (5)	C16—C17—C18—C19	1.4 (6)
N1—C7—C8—C11	178.7 (3)	C17—C18—C19—C20	0.1 (5)
O1—C7—C8—C9	178.8 (3)	C17—C18—C19—Br1	−178.7 (3)
N1—C7—C8—C9	−0.3 (3)	C18—C19—C20—C15	−2.0 (5)
N1—N2—C9—C8	−0.8 (3)	Br1—C19—C20—C15	176.7 (2)
N1—N2—C9—C10	178.1 (3)	C16—C15—C20—C19	2.5 (5)
C7—C8—C9—N2	0.7 (3)	N3—C15—C20—C19	179.0 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84 (1)	1.68 (3)	2.468 (3)	154 (6)
N3—H3···O2	0.88 (1)	1.87 (3)	2.617 (4)	142 (4)
C14—H14B···Cg1ⁱ	0.98	2.69	3.495 (4)	140

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈BrN₃O₂
M_r	412.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.7065 (5), 11.7982 (8), 17.5954 (12)
β (°)	101.536 (6)
V (Å³)	1770.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.34
Crystal size (mm)	0.25 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.592, 0.892
No. of measured, independent and observed [I > 2σ(I)] reflections	7812, 4041, 3033
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.105, 1.01
No. of reflections	4041
No. of parameters	245
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.58, −0.47

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the N1/N2/C7–C9 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.843 (10)	1.68 (3)	2.468 (3)	154 (6)
N3—H3···O2	0.881 (10)	1.87 (3)	2.617 (4)	142 (4)
C14—H14B···Cg1ⁱ	0.98	2.69	3.495 (4)	140

Symmetry code: (i) −x, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: aasiri2@kau.edu.sa.

Acknowledgements

The authors are thankful to the Center of Excellence for Advanced Materials Research and the Chemistry Department of King Abdulaziz University for providing research facilities. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Asiri, A. M., Al-Youbi, A. O., Alamry, K. A., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2157. Web of Science CSD CrossRef IUCr Journals Google Scholar
Asiri, A. M., Al-Youbi, A. O., Faidallah, H. M., Ng, S. W. & Tiekink, E. R. T. (2011). Acta Cryst. E67, o2353. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bendaas, A., Hamdi, M. & Sellier, N. (1999). J. Heterocycl. Chem. 36, 1291–1294. CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gelin, S., Chantegrel, B. & Nadi, A. I. (1983). J. Org. Chem. 48, 4078–4082. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Page o813

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2Z)-3-(3-Bromo­anilino)-1-(5-hy­dr­oxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one

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Experimental

Crystal data

Data collection

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organic compounds

(2Z)-3-(3-Bromoanilino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one