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

Asiri, A.M.; Al-Youbi, A.O.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006526

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o794

doi:10.1107/S1600536812006526

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

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^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 12 February 2012; accepted 14 February 2012; online 24 February 2012)

A twist is evident in the title compound, C₂₁H₂₁N₃O₂, the dihedral angle between the terminal six-membered rings being 29.46 (10)°; the linked five- and six-membered rings are coplanar [1.30 (11)°]. The carbonyl O atom accepts intramolecular hydrogen bonds from the adjacent hydroxy and amine groups. The three-dimensional crystal packing is achieved through 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 analogues, see: Asiri, Al-Youbi, Alamry et al. (2011 ); Asiri, Al-Youbi, Faidallah et al. (2011 ).

Experimental

Crystal data

C₂₁H₂₁N₃O₂
M_r = 347.41
Monoclinic, P 2₁ /c
a = 14.9041 (8) Å
b = 6.9222 (4) Å
c = 17.1921 (8) Å
β = 96.190 (5)°
V = 1763.35 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.40 × 0.02 × 0.02 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.967, T_max = 0.998
12780 measured reflections
4055 independent reflections
2455 reflections with I > 2σ(I)
R_int = 0.076

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.164
S = 1.02
4055 reflections
246 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.86 (1)	1.71 (2)	2.509 (2)	155 (4)
N3—H2⋯O2	0.89 (1)	1.91 (2)	2.671 (3)	143 (2)
C14—H14A⋯Cg1ⁱ	0.98	2.69	3.475 (2)	138
C14—H14C⋯Cg1ⁱⁱ	0.98	2.66	3.563 (2)	153
C17—H17⋯Cg2ⁱⁱⁱ	0.95	2.58	3.424 (2)	148
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x, y-{\script{1\over 2}}]$ , $[-z+{\script{1\over 2}}]$ .

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/S1600536812006526/hg5179sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006526/hg5179Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006526/hg5179Isup3.cml

checkCIF report

Comment top

In connection with recent structural studies (Asiri, Al-Youbi, Alamry et al., 2011; (Asiri, Al-Youbi, Faidallah et al., 2011) of compounds prepared by reactions between pyrazoles and aniline derivatives following literature procedures (Gelin et al., 1983; Bendaas et al., 1999), the title compound, 3-(4-toluidino)-1-(5-hydroxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)but-2-en-1-one (I) was investigated.

While in (I), Fig. 1, the linked five- and six-membered rings are co-planar, forming a dihedral angle of 1.30 (11)°, there is a twist about the N3—C15 bond as seen in the value of the C13—N3—C15—C16 torsion angle of 146.9 (2)°; the dihedral angle between the terminal six-membered rings is 29.46 (10)°. The carbonyl-O2 atom accepts hydrogen bonds from the adjacent hydroxyl- and amine-groups, Table 1. These groups do not participate in intermolecular interactions. Rather, molecules are consolidated in the three-dimensional crystal packing by C—H···π interactions, Fig. 2 and Table 1.

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 analogues, 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 p-toluidine (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 as yellow needles; M.pt: 419–421 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 a axis of the unit-cell contents of (I). The C—H···π interactions are shown as purple dashed lines.

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

Crystal data top

C₂₁H₂₁N₃O₂	F(000) = 736
M_r = 347.41	D_x = 1.309 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2466 reflections
a = 14.9041 (8) Å	θ = 2.4–27.5°
b = 6.9222 (4) Å	µ = 0.09 mm⁻¹
c = 17.1921 (8) Å	T = 100 K
β = 96.190 (5)°	Needle, yellow
V = 1763.35 (16) Å³	0.40 × 0.02 × 0.02 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4055 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2455 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.076
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.4°
ω scan	h = −18→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
T_min = 0.967, T_max = 0.998	l = −22→18
12780 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.065P)² + 0.099P] where P = (F_o² + 2F_c²)/3
4055 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.24 e Å⁻³
2 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₂	V = 1763.35 (16) Å³
M_r = 347.41	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.9041 (8) Å	µ = 0.09 mm⁻¹
b = 6.9222 (4) Å	T = 100 K
c = 17.1921 (8) Å	0.40 × 0.02 × 0.02 mm
β = 96.190 (5)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4055 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2455 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.998	R_int = 0.076
12780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	2 restraints
wR(F²) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.24 e Å⁻³
4055 reflections	Δρ_min = −0.29 e Å⁻³
246 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.50304 (12)	0.0677 (2)	0.39888 (10)	0.0275 (4)
O2	0.37132 (11)	0.0655 (2)	0.29485 (9)	0.0244 (4)
N1	0.64285 (13)	0.0686 (2)	0.34357 (10)	0.0192 (4)
N2	0.67114 (13)	0.0711 (2)	0.26853 (10)	0.0229 (4)
N3	0.23145 (13)	0.0409 (3)	0.18426 (11)	0.0215 (4)
C1	0.70881 (15)	0.0615 (3)	0.40934 (12)	0.0186 (5)
C2	0.68417 (16)	0.0546 (3)	0.48530 (13)	0.0231 (5)
H2A	0.6223	0.0541	0.4941	0.028*
C3	0.75125 (17)	0.0486 (3)	0.54797 (13)	0.0256 (5)
H3	0.7347	0.0431	0.5998	0.031*
C4	0.84175 (17)	0.0503 (3)	0.53633 (13)	0.0257 (5)
H4	0.8870	0.0465	0.5797	0.031*
C5	0.86567 (17)	0.0577 (3)	0.46044 (13)	0.0245 (5)
H5	0.9276	0.0600	0.4519	0.029*
C6	0.79969 (15)	0.0618 (3)	0.39707 (13)	0.0227 (5)
H6	0.8165	0.0649	0.3453	0.027*
C7	0.55156 (15)	0.0701 (3)	0.33854 (13)	0.0193 (5)
C8	0.51783 (15)	0.0733 (3)	0.25960 (12)	0.0187 (5)
C9	0.59647 (16)	0.0733 (3)	0.21952 (13)	0.0215 (5)
C10	0.60368 (17)	0.0740 (3)	0.13342 (13)	0.0302 (6)
H10A	0.6674	0.0793	0.1243	0.045*
H10B	0.5721	0.1871	0.1096	0.045*
H10C	0.5763	−0.0439	0.1100	0.045*
C11	0.42170 (16)	0.0712 (3)	0.23786 (13)	0.0207 (5)
C12	0.38378 (16)	0.0712 (3)	0.15824 (12)	0.0205 (5)
H12	0.4245	0.0831	0.1196	0.025*
C13	0.29317 (16)	0.0556 (3)	0.13212 (12)	0.0200 (5)
C14	0.26394 (16)	0.0493 (3)	0.04612 (12)	0.0229 (5)
H14A	0.2209	−0.0566	0.0348	0.034*
H14B	0.3167	0.0283	0.0177	0.034*
H14C	0.2351	0.1720	0.0296	0.034*
C15	0.13787 (16)	0.0037 (3)	0.17314 (13)	0.0209 (5)
C16	0.10125 (15)	−0.1006 (3)	0.23183 (12)	0.0225 (5)
H16	0.1400	−0.1484	0.2751	0.027*
C17	0.00953 (16)	−0.1349 (3)	0.22785 (13)	0.0231 (5)
H17	−0.0138	−0.2033	0.2692	0.028*
C18	−0.04959 (16)	−0.0719 (3)	0.16470 (13)	0.0227 (5)
C19	−0.01234 (16)	0.0307 (3)	0.10594 (13)	0.0229 (5)
H19	−0.0509	0.0746	0.0618	0.028*
C20	0.07922 (16)	0.0702 (3)	0.11024 (12)	0.0227 (5)
H20	0.1022	0.1432	0.0700	0.027*
C21	−0.14922 (16)	−0.1052 (3)	0.16189 (14)	0.0295 (6)
H21	−0.1795	−0.0515	0.1132	0.044*
H21B	−0.1721	−0.0416	0.2067	0.044*
H21C	−0.1612	−0.2442	0.1639	0.044*
H1	0.4494 (12)	0.069 (5)	0.375 (2)	0.102 (15)*
H2	0.2582 (15)	0.034 (3)	0.2329 (7)	0.031 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0212 (10)	0.0405 (10)	0.0217 (9)	−0.0003 (8)	0.0060 (8)	−0.0002 (7)
O2	0.0207 (9)	0.0336 (9)	0.0199 (8)	−0.0008 (7)	0.0060 (7)	0.0005 (6)
N1	0.0186 (10)	0.0209 (9)	0.0184 (9)	0.0007 (7)	0.0039 (8)	−0.0005 (7)
N2	0.0219 (11)	0.0283 (10)	0.0190 (10)	−0.0012 (8)	0.0048 (8)	−0.0007 (7)
N3	0.0180 (11)	0.0307 (11)	0.0159 (10)	−0.0003 (8)	0.0016 (8)	0.0020 (8)
C1	0.0204 (12)	0.0138 (10)	0.0216 (11)	0.0004 (9)	0.0024 (9)	0.0017 (8)
C2	0.0235 (13)	0.0237 (11)	0.0224 (12)	0.0006 (10)	0.0039 (10)	−0.0017 (9)
C3	0.0288 (14)	0.0278 (12)	0.0203 (12)	0.0009 (10)	0.0028 (10)	−0.0003 (9)
C4	0.0277 (14)	0.0269 (12)	0.0213 (12)	−0.0019 (10)	−0.0024 (10)	−0.0005 (9)
C5	0.0224 (13)	0.0253 (12)	0.0256 (12)	−0.0007 (10)	0.0022 (10)	0.0008 (9)
C6	0.0218 (13)	0.0208 (11)	0.0254 (12)	−0.0010 (9)	0.0029 (10)	−0.0005 (9)
C7	0.0182 (12)	0.0175 (10)	0.0230 (12)	−0.0001 (9)	0.0058 (9)	−0.0005 (8)
C8	0.0184 (12)	0.0172 (10)	0.0203 (11)	−0.0008 (9)	0.0018 (9)	0.0009 (8)
C9	0.0218 (13)	0.0209 (11)	0.0218 (12)	−0.0001 (9)	0.0022 (10)	0.0009 (8)
C10	0.0248 (14)	0.0447 (15)	0.0214 (12)	0.0012 (11)	0.0038 (11)	0.0016 (10)
C11	0.0219 (13)	0.0164 (10)	0.0244 (12)	0.0002 (9)	0.0046 (10)	0.0007 (8)
C12	0.0216 (12)	0.0208 (11)	0.0196 (11)	−0.0004 (9)	0.0047 (9)	0.0009 (8)
C13	0.0230 (13)	0.0171 (10)	0.0202 (11)	0.0002 (9)	0.0043 (10)	0.0013 (8)
C14	0.0249 (13)	0.0261 (12)	0.0187 (11)	0.0002 (10)	0.0067 (10)	0.0002 (9)
C15	0.0195 (13)	0.0227 (11)	0.0205 (11)	−0.0008 (9)	0.0026 (9)	−0.0036 (8)
C16	0.0218 (13)	0.0237 (12)	0.0214 (12)	0.0037 (9)	0.0000 (10)	0.0018 (8)
C17	0.0250 (13)	0.0234 (11)	0.0219 (12)	−0.0010 (10)	0.0070 (10)	0.0026 (9)
C18	0.0226 (13)	0.0217 (11)	0.0239 (12)	0.0032 (9)	0.0026 (10)	−0.0041 (9)
C19	0.0232 (13)	0.0270 (12)	0.0176 (11)	0.0038 (9)	−0.0022 (10)	−0.0030 (8)
C20	0.0247 (13)	0.0249 (11)	0.0185 (11)	0.0027 (10)	0.0029 (10)	0.0019 (9)
C21	0.0260 (14)	0.0347 (13)	0.0279 (13)	−0.0015 (11)	0.0038 (11)	−0.0017 (10)

Geometric parameters (Å, º) top

O1—C7	1.327 (3)	C10—H10A	0.9800
O1—H1	0.858 (10)	C10—H10B	0.9800
O2—C11	1.298 (3)	C10—H10C	0.9800
N1—C7	1.354 (3)	C11—C12	1.423 (3)
N1—N2	1.400 (2)	C12—C13	1.381 (3)
N1—C1	1.417 (3)	C12—H12	0.9500
N2—C9	1.322 (3)	C13—C14	1.496 (3)
N3—C13	1.356 (3)	C14—H14A	0.9800
N3—C15	1.411 (3)	C14—H14B	0.9800
N3—H2	0.888 (10)	C14—H14C	0.9800
C1—C6	1.393 (3)	C15—C20	1.393 (3)
C1—C2	1.395 (3)	C15—C16	1.398 (3)
C2—C3	1.389 (3)	C16—C17	1.382 (3)
C2—H2A	0.9500	C16—H16	0.9500
C3—C4	1.385 (3)	C17—C18	1.393 (3)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.390 (3)	C18—C19	1.398 (3)
C4—H4	0.9500	C18—C21	1.498 (3)
C5—C6	1.387 (3)	C19—C20	1.386 (3)
C5—H5	0.9500	C19—H19	0.9500
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.396 (3)	C21—H21	0.9800
C8—C9	1.422 (3)	C21—H21B	0.9800
C8—C11	1.441 (3)	C21—H21C	0.9800
C9—C10	1.496 (3)

C7—O1—H1	101 (3)	H10B—C10—H10C	109.5
C7—N1—N2	109.97 (18)	O2—C11—C12	121.6 (2)
C7—N1—C1	131.08 (18)	O2—C11—C8	116.39 (19)
N2—N1—C1	118.94 (18)	C12—C11—C8	122.0 (2)
C9—N2—N1	105.72 (18)	C13—C12—C11	125.9 (2)
C13—N3—C15	130.94 (19)	C13—C12—H12	117.1
C13—N3—H2	111.0 (16)	C11—C12—H12	117.1
C15—N3—H2	117.1 (16)	N3—C13—C12	120.0 (2)
C6—C1—C2	120.0 (2)	N3—C13—C14	120.3 (2)
C6—C1—N1	118.77 (19)	C12—C13—C14	119.61 (19)
C2—C1—N1	121.2 (2)	C13—C14—H14A	109.5
C3—C2—C1	119.1 (2)	C13—C14—H14B	109.5
C3—C2—H2A	120.4	H14A—C14—H14B	109.5
C1—C2—H2A	120.4	C13—C14—H14C	109.5
C4—C3—C2	121.2 (2)	H14A—C14—H14C	109.5
C4—C3—H3	119.4	H14B—C14—H14C	109.5
C2—C3—H3	119.4	C20—C15—C16	118.0 (2)
C3—C4—C5	119.2 (2)	C20—C15—N3	125.0 (2)
C3—C4—H4	120.4	C16—C15—N3	117.0 (2)
C5—C4—H4	120.4	C17—C16—C15	120.9 (2)
C6—C5—C4	120.4 (2)	C17—C16—H16	119.5
C6—C5—H5	119.8	C15—C16—H16	119.5
C4—C5—H5	119.8	C16—C17—C18	121.6 (2)
C5—C6—C1	120.0 (2)	C16—C17—H17	119.2
C5—C6—H6	120.0	C18—C17—H17	119.2
C1—C6—H6	120.0	C17—C18—C19	117.1 (2)
O1—C7—N1	125.3 (2)	C17—C18—C21	121.2 (2)
O1—C7—C8	126.2 (2)	C19—C18—C21	121.6 (2)
N1—C7—C8	108.45 (19)	C20—C19—C18	121.8 (2)
C7—C8—C9	104.0 (2)	C20—C19—H19	119.1
C7—C8—C11	119.7 (2)	C18—C19—H19	119.1
C9—C8—C11	136.3 (2)	C19—C20—C15	120.5 (2)
N2—C9—C8	111.87 (19)	C19—C20—H20	119.7
N2—C9—C10	119.0 (2)	C15—C20—H20	119.7
C8—C9—C10	129.1 (2)	C18—C21—H21	109.5
C9—C10—H10A	109.5	C18—C21—H21B	109.5
C9—C10—H10B	109.5	H21—C21—H21B	109.5
H10A—C10—H10B	109.5	C18—C21—H21C	109.5
C9—C10—H10C	109.5	H21—C21—H21C	109.5
H10A—C10—H10C	109.5	H21B—C21—H21C	109.5

C7—N1—N2—C9	−0.2 (2)	C11—C8—C9—N2	−178.4 (2)
C1—N1—N2—C9	178.60 (16)	C7—C8—C9—C10	179.3 (2)
C7—N1—C1—C6	−180.0 (2)	C11—C8—C9—C10	1.1 (4)
N2—N1—C1—C6	1.5 (3)	C7—C8—C11—O2	−0.3 (3)
C7—N1—C1—C2	−0.1 (3)	C9—C8—C11—O2	177.8 (2)
N2—N1—C1—C2	−178.62 (17)	C7—C8—C11—C12	−179.00 (18)
C6—C1—C2—C3	0.1 (3)	C9—C8—C11—C12	−1.0 (4)
N1—C1—C2—C3	−179.74 (17)	O2—C11—C12—C13	−3.5 (3)
C1—C2—C3—C4	0.4 (3)	C8—C11—C12—C13	175.14 (19)
C2—C3—C4—C5	−0.2 (3)	C15—N3—C13—C12	−172.5 (2)
C3—C4—C5—C6	−0.5 (3)	C15—N3—C13—C14	5.7 (3)
C4—C5—C6—C1	1.0 (3)	C11—C12—C13—N3	0.9 (3)
C2—C1—C6—C5	−0.8 (3)	C11—C12—C13—C14	−177.35 (18)
N1—C1—C6—C5	179.08 (17)	C13—N3—C15—C20	−36.1 (3)
N2—N1—C7—O1	179.73 (18)	C13—N3—C15—C16	146.9 (2)
C1—N1—C7—O1	1.1 (3)	C20—C15—C16—C17	−0.6 (3)
N2—N1—C7—C8	0.1 (2)	N3—C15—C16—C17	176.58 (19)
C1—N1—C7—C8	−178.55 (18)	C15—C16—C17—C18	1.6 (3)
O1—C7—C8—C9	−179.57 (19)	C16—C17—C18—C19	−1.0 (3)
N1—C7—C8—C9	0.1 (2)	C16—C17—C18—C21	−178.35 (19)
O1—C7—C8—C11	−1.0 (3)	C17—C18—C19—C20	−0.6 (3)
N1—C7—C8—C11	178.65 (17)	C21—C18—C19—C20	176.7 (2)
N1—N2—C9—C8	0.3 (2)	C18—C19—C20—C15	1.7 (3)
N1—N2—C9—C10	−179.30 (17)	C16—C15—C20—C19	−1.0 (3)
C7—C8—C9—N2	−0.2 (2)	N3—C15—C20—C19	−177.94 (19)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.86 (1)	1.71 (2)	2.509 (2)	155 (4)
N3—H2···O2	0.89 (1)	1.91 (2)	2.671 (3)	143 (2)
C14—H14A···Cg2ⁱ	0.98	2.69	3.475 (2)	138
C14—H14C···Cg2ⁱⁱ	0.98	2.66	3.563 (2)	153
C17—H17···Cg3ⁱⁱⁱ	0.95	2.58	3.424 (2)	148

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₂
M_r	347.41
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	14.9041 (8), 6.9222 (4), 17.1921 (8)
β (°)	96.190 (5)
V (Å³)	1763.35 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.02 × 0.02

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.967, 0.998
No. of measured, independent and observed [I > 2σ(I)] reflections	12780, 4055, 2455
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.164, 1.02
No. of reflections	4055
No. of parameters	246
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)	0.24, −0.29

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 and Cg2 are the centroids of the C1–C6 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.86 (1)	1.71 (2)	2.509 (2)	155 (4)
N3—H2···O2	0.89 (1)	1.91 (2)	2.671 (3)	143 (2)
C14—H14A···Cg2ⁱ	0.98	2.69	3.475 (2)	138
C14—H14C···Cg2ⁱⁱ	0.98	2.66	3.563 (2)	153
C17—H17···Cg3ⁱⁱⁱ	0.95	2.58	3.424 (2)	148

Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+1, y+1/2, −z+1/2; (iii) −x, y−1/2, −z+1/2.

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

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Experimental

Crystal data

Data collection

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organic compounds

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