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

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

doi:10.1107/S1600536811032491

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2353

doi:10.1107/S1600536811032491

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

Abdullah M. Asiri,^a,^b ‡ Abdulrahman O. Al-Youbi,^a Hassan M. Faidallah,^a Seik Weng Ng ^c,^a 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 8 August 2011; accepted 10 August 2011; online 17 August 2011)

The central residue in the title compound, C₂₁H₂₁N₃O₃, is close to planar (r.m.s. deviation = 0.0753 Å for all non-H atoms from OH to NH inclusive): the hydroxy, amino and carbonyl groups all lie to the same side of the molecule (the conformation about the ethene bond is Z), facilitating the formation of intramolecular O—H⋯O and N—H⋯O hydrogen bonds that close S(6) rings. However, overall the molecule is twisted as the terminal aromatic rings are not coplanar with the central plane [dihedral angles = 20.55 (5) and 80.90 (4)° for the N-bound phenyl ring and the methoxybenzene ring, respectively]. The dihedral angle between the rings is 82.14 (7)°. Supramolecular layers in the ac plane mediated by C—H⋯π interactions are found in the crystal.

Related literature

For background to the synthesis, see: Gelin et al. (1983 ); Bendaas et al. (1999 ). For the structure of the 4-chloro derivative, see: Asiri et al. (2011 ).

Experimental

Crystal data

C₂₁H₂₁N₃O₃
M_r = 363.41
Monoclinic, P 2₁ /n
a = 9.5717 (3) Å
b = 16.9516 (6) Å
c = 11.3143 (4) Å
β = 104.946 (4)°
V = 1773.70 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.837, T_max = 1.000
8486 measured reflections
3939 independent reflections
3145 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.05
3939 reflections
255 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N1,N2,C1–C3 and C15–C20 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.86 (1)	1.68 (1)	2.4963 (15)	156 (2)
N3—H3⋯O2	0.89 (1)	1.92 (1)	2.6447 (16)	138 (2)
C14—H14b⋯Cg1ⁱ	0.98	2.88	3.5542 (18)	127
C21—H21c⋯Cg2ⁱⁱ	0.98	2.76	3.5195 (17)	134
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+2, -y+1, -z.

Data collection: CrysAlis PRO (Agilent, 2010); 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/S1600536811032491/hb6355sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032491/hb6355Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032491/hb6355Isup3.cml

checkCIF report

Comment top

In connection with a recent structural study (Asiri et al., 2011), the title compound (I) was prepared as a part of on-going investigations of reactions between pyrazoles and aniline derivatives (Gelin et al., 1983; Bendaas et al., 1999).

The molecular structure of (I), Fig. 1, resembles closely that of the 4-chloroanilino derivative (Asiri et al., 2011) and features a Z configuration about the C12—C13 [1.381 (2) Å] bond. The hydroxy and amino groups are syn to the central carbonyl group and each forms a hydrogen bond to close a S(6) ring (Table 1). A direct consequence of this is that the central residue is planar; the values of the C1—C2—C11—O2, C2—C11—C12—C13 and C11—C12—C13—N3 torsion angles are -3.6 (2), -171.74 (15) and -1.7 (2) °, respectively. The benzene and 4-methoxybenzene rings are each twisted out of the central plane as seen in the values of the C1—N1—C5—C6 and C13—N3—C15—C16 torsion angles of 159.97 (15) and -74.5 (2) °, respectively.

The most prominent feature of the crystal packing is the formation of supramolecular layers in the ac plane and mediated by C—H···π interactions, Fig. 2. and Table 1. Layers stack along the b axis as shown in Fig. 3.

Related literature top

For background to the synthesis, see: Gelin et al. (1983); Bendaas et al. (1999). For the structure of the 4-chloro derivative, see: Asiri et al. (2011).

Experimental top

A solution of 4-acetoacetyl-5-hydroxy-3-methyl-1-p-sulfamylphenypyrazole (1.7 g, 0.005 mole) and 4-methoxyaniline (0.63 g, 0.005 mole) in ethanol (25 ml) was refluxed for 2 h. The precipitate, obtained from the hot solution, was collected, washed with methanol and recrystallized from ethanol-benzene as yellow blocks; M.pt: 507–507 K.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of a supramolecular layer in (I) mediated by C—H···π interactions, shown as purple dashed lines
	Fig. 3. Stacking of supramolecular layers along the b axis in (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-methoxyanilino)but-2-en-1-one top

Crystal data top

C₂₁H₂₁N₃O₃	F(000) = 768
M_r = 363.41	D_x = 1.361 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3917 reflections
a = 9.5717 (3) Å	θ = 2.4–29.3°
b = 16.9516 (6) Å	µ = 0.09 mm⁻¹
c = 11.3143 (4) Å	T = 100 K
β = 104.946 (4)°	Block, yellow
V = 1773.70 (10) Å³	0.30 × 0.25 × 0.20 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3939 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3145 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.024
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→21
T_min = 0.837, T_max = 1.000	l = −14→14
8486 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0364P)² + 0.8331P] where P = (F_o² + 2F_c²)/3
3939 reflections	(Δ/σ)_max < 0.001
255 parameters	Δρ_max = 0.27 e Å⁻³
2 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₁H₂₁N₃O₃	V = 1773.70 (10) Å³
M_r = 363.41	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.5717 (3) Å	µ = 0.09 mm⁻¹
b = 16.9516 (6) Å	T = 100 K
c = 11.3143 (4) Å	0.30 × 0.25 × 0.20 mm
β = 104.946 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3939 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3145 reflections with I > 2σ(I)
T_min = 0.837, T_max = 1.000	R_int = 0.024
8486 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	2 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
3939 reflections	Δρ_min = −0.23 e Å⁻³
255 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
O1	0.14980 (12)	0.66071 (7)	0.33592 (9)	0.0222 (3)
O2	0.37382 (11)	0.60631 (7)	0.29255 (9)	0.0213 (3)
O3	0.91460 (11)	0.58562 (7)	−0.12793 (9)	0.0219 (3)
N1	0.17619 (13)	0.67412 (8)	0.54868 (11)	0.0166 (3)
N2	0.28248 (13)	0.65978 (8)	0.65708 (11)	0.0175 (3)
N3	0.61937 (14)	0.57378 (8)	0.23667 (11)	0.0195 (3)
C1	0.22616 (16)	0.65491 (9)	0.45138 (13)	0.0170 (3)
C2	0.36749 (16)	0.62804 (9)	0.49321 (13)	0.0169 (3)
C3	0.39577 (15)	0.63279 (9)	0.62323 (13)	0.0162 (3)
C4	0.52961 (16)	0.61127 (10)	0.71833 (13)	0.0196 (3)
H4A	0.5134	0.6184	0.7997	0.029*
H4B	0.6094	0.6452	0.7101	0.029*
H4C	0.5540	0.5560	0.7078	0.029*
C5	0.04095 (15)	0.70640 (9)	0.55398 (13)	0.0166 (3)
C6	−0.00329 (16)	0.69838 (9)	0.66119 (13)	0.0187 (3)
H6	0.0562	0.6716	0.7296	0.022*
C7	−0.13461 (16)	0.72972 (10)	0.66734 (14)	0.0217 (3)
H7	−0.1651	0.7245	0.7405	0.026*
C8	−0.22213 (17)	0.76870 (10)	0.56770 (15)	0.0247 (4)
H8	−0.3126	0.7898	0.5722	0.030*
C9	−0.17707 (17)	0.77671 (10)	0.46184 (14)	0.0235 (4)
H9	−0.2367	0.8036	0.3936	0.028*
C10	−0.04527 (17)	0.74579 (10)	0.45410 (14)	0.0205 (3)
H10	−0.0146	0.7516	0.3811	0.025*
C11	0.44652 (16)	0.60431 (9)	0.40619 (13)	0.0176 (3)
C12	0.59321 (16)	0.58162 (9)	0.44007 (13)	0.0175 (3)
H12	0.6385	0.5752	0.5247	0.021*
C13	0.67514 (16)	0.56811 (9)	0.35792 (13)	0.0176 (3)
C14	0.83048 (16)	0.54384 (10)	0.40247 (14)	0.0211 (3)
H14A	0.8907	0.5790	0.3677	0.032*
H14B	0.8417	0.4895	0.3769	0.032*
H14C	0.8606	0.5471	0.4919	0.032*
C15	0.70003 (15)	0.57341 (10)	0.14592 (13)	0.0179 (3)
C16	0.77859 (16)	0.63978 (10)	0.13037 (13)	0.0193 (3)
H16	0.7840	0.6838	0.1834	0.023*
C17	0.84893 (16)	0.64190 (10)	0.03781 (13)	0.0190 (3)
H17	0.9022	0.6874	0.0271	0.023*
C18	0.84160 (15)	0.57738 (9)	−0.03966 (13)	0.0172 (3)
C19	0.76391 (16)	0.51053 (10)	−0.02410 (13)	0.0193 (3)
H19	0.7589	0.4663	−0.0766	0.023*
C20	0.69349 (16)	0.50912 (10)	0.06938 (13)	0.0196 (3)
H20	0.6405	0.4636	0.0807	0.023*
C21	0.90919 (17)	0.52107 (10)	−0.21023 (13)	0.0223 (3)
H21A	0.9647	0.5343	−0.2692	0.033*
H21B	0.8084	0.5106	−0.2540	0.033*
H21C	0.9507	0.4740	−0.1640	0.033*
H1	0.214 (2)	0.6449 (15)	0.300 (2)	0.067 (8)*
H3	0.5266 (11)	0.5872 (11)	0.2149 (16)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0225 (6)	0.0292 (7)	0.0142 (5)	0.0037 (5)	0.0039 (4)	−0.0013 (5)
O2	0.0214 (5)	0.0273 (6)	0.0154 (5)	0.0025 (5)	0.0049 (4)	−0.0012 (4)
O3	0.0259 (6)	0.0232 (6)	0.0198 (5)	−0.0003 (5)	0.0119 (5)	0.0004 (4)
N1	0.0172 (6)	0.0178 (7)	0.0141 (6)	0.0020 (5)	0.0027 (5)	0.0006 (5)
N2	0.0187 (6)	0.0179 (7)	0.0149 (6)	0.0010 (5)	0.0024 (5)	0.0007 (5)
N3	0.0178 (6)	0.0250 (8)	0.0171 (6)	0.0018 (6)	0.0070 (5)	−0.0006 (5)
C1	0.0207 (7)	0.0155 (8)	0.0150 (7)	−0.0020 (6)	0.0048 (6)	−0.0008 (6)
C2	0.0185 (7)	0.0158 (8)	0.0166 (7)	−0.0001 (6)	0.0050 (6)	0.0000 (6)
C3	0.0181 (7)	0.0138 (7)	0.0172 (7)	−0.0021 (6)	0.0055 (6)	−0.0004 (6)
C4	0.0204 (7)	0.0215 (8)	0.0172 (7)	0.0024 (6)	0.0053 (6)	−0.0002 (6)
C5	0.0159 (7)	0.0145 (8)	0.0193 (7)	−0.0009 (6)	0.0042 (6)	−0.0029 (6)
C6	0.0183 (7)	0.0189 (8)	0.0184 (7)	−0.0013 (6)	0.0036 (6)	−0.0002 (6)
C7	0.0201 (7)	0.0254 (9)	0.0208 (7)	−0.0020 (7)	0.0075 (6)	−0.0022 (6)
C8	0.0181 (7)	0.0273 (9)	0.0288 (8)	0.0025 (7)	0.0060 (7)	−0.0032 (7)
C9	0.0217 (8)	0.0232 (9)	0.0234 (8)	0.0040 (7)	0.0018 (6)	0.0020 (6)
C10	0.0230 (8)	0.0205 (8)	0.0183 (7)	0.0006 (6)	0.0060 (6)	0.0010 (6)
C11	0.0225 (7)	0.0137 (8)	0.0169 (7)	−0.0013 (6)	0.0056 (6)	−0.0003 (6)
C12	0.0205 (7)	0.0178 (8)	0.0145 (7)	0.0001 (6)	0.0051 (6)	−0.0005 (6)
C13	0.0204 (7)	0.0142 (8)	0.0178 (7)	−0.0013 (6)	0.0040 (6)	−0.0009 (6)
C14	0.0210 (7)	0.0231 (9)	0.0202 (7)	0.0018 (6)	0.0072 (6)	−0.0007 (6)
C15	0.0168 (7)	0.0225 (9)	0.0149 (7)	0.0027 (6)	0.0046 (6)	0.0013 (6)
C16	0.0205 (7)	0.0180 (8)	0.0188 (7)	0.0039 (6)	0.0039 (6)	−0.0011 (6)
C17	0.0189 (7)	0.0174 (8)	0.0205 (7)	0.0011 (6)	0.0045 (6)	0.0034 (6)
C18	0.0151 (7)	0.0215 (8)	0.0145 (7)	0.0041 (6)	0.0030 (6)	0.0041 (6)
C19	0.0210 (7)	0.0194 (8)	0.0170 (7)	0.0009 (6)	0.0039 (6)	−0.0022 (6)
C20	0.0202 (7)	0.0197 (8)	0.0191 (7)	−0.0020 (6)	0.0056 (6)	0.0001 (6)
C21	0.0235 (8)	0.0273 (9)	0.0178 (7)	0.0040 (7)	0.0083 (6)	−0.0011 (6)

Geometric parameters (Å, º) top

O1—C1	1.3259 (17)	C8—C9	1.380 (2)
O1—H1	0.864 (10)	C8—H8	0.9500
O2—C11	1.2950 (17)	C9—C10	1.390 (2)
O3—C18	1.3657 (17)	C9—H9	0.9500
O3—C21	1.4291 (19)	C10—H10	0.9500
N1—C1	1.3484 (19)	C11—C12	1.410 (2)
N1—N2	1.3981 (16)	C12—C13	1.381 (2)
N1—C5	1.4208 (19)	C12—H12	0.9500
N2—C3	1.3213 (19)	C13—C14	1.499 (2)
N3—C13	1.3410 (19)	C14—H14A	0.9800
N3—C15	1.4350 (19)	C14—H14B	0.9800
N3—H3	0.888 (9)	C14—H14C	0.9800
C1—C2	1.390 (2)	C15—C20	1.383 (2)
C2—C3	1.4277 (19)	C15—C16	1.389 (2)
C2—C11	1.445 (2)	C16—C17	1.384 (2)
C3—C4	1.490 (2)	C16—H16	0.9500
C4—H4A	0.9800	C17—C18	1.392 (2)
C4—H4B	0.9800	C17—H17	0.9500
C4—H4C	0.9800	C18—C19	1.391 (2)
C5—C10	1.387 (2)	C19—C20	1.393 (2)
C5—C6	1.391 (2)	C19—H19	0.9500
C6—C7	1.383 (2)	C20—H20	0.9500
C6—H6	0.9500	C21—H21A	0.9800
C7—C8	1.386 (2)	C21—H21B	0.9800
C7—H7	0.9500	C21—H21C	0.9800

C1—O1—H1	99.0 (16)	C9—C10—H10	120.3
C18—O3—C21	117.30 (12)	O2—C11—C12	121.30 (13)
C1—N1—N2	110.07 (12)	O2—C11—C2	115.32 (13)
C1—N1—C5	130.27 (12)	C12—C11—C2	123.38 (13)
N2—N1—C5	119.65 (11)	C13—C12—C11	124.10 (13)
C3—N2—N1	105.77 (11)	C13—C12—H12	118.0
C13—N3—C15	125.88 (13)	C11—C12—H12	118.0
C13—N3—H3	114.1 (12)	N3—C13—C12	122.10 (13)
C15—N3—H3	119.1 (12)	N3—C13—C14	117.52 (13)
O1—C1—N1	124.40 (13)	C12—C13—C14	120.35 (13)
O1—C1—C2	126.92 (14)	C13—C14—H14A	109.5
N1—C1—C2	108.68 (12)	C13—C14—H14B	109.5
C1—C2—C3	103.98 (13)	H14A—C14—H14B	109.5
C1—C2—C11	119.59 (13)	C13—C14—H14C	109.5
C3—C2—C11	136.42 (14)	H14A—C14—H14C	109.5
N2—C3—C2	111.50 (13)	H14B—C14—H14C	109.5
N2—C3—C4	119.49 (12)	C20—C15—C16	119.82 (14)
C2—C3—C4	129.00 (13)	C20—C15—N3	120.37 (14)
C3—C4—H4A	109.5	C16—C15—N3	119.71 (14)
C3—C4—H4B	109.5	C17—C16—C15	120.12 (15)
H4A—C4—H4B	109.5	C17—C16—H16	119.9
C3—C4—H4C	109.5	C15—C16—H16	119.9
H4A—C4—H4C	109.5	C16—C17—C18	120.05 (15)
H4B—C4—H4C	109.5	C16—C17—H17	120.0
C10—C5—C6	120.45 (14)	C18—C17—H17	120.0
C10—C5—N1	120.55 (13)	O3—C18—C19	124.54 (14)
C6—C5—N1	119.00 (13)	O3—C18—C17	115.33 (14)
C7—C6—C5	119.44 (14)	C19—C18—C17	120.13 (14)
C7—C6—H6	120.3	C18—C19—C20	119.28 (14)
C5—C6—H6	120.3	C18—C19—H19	120.4
C6—C7—C8	120.57 (14)	C20—C19—H19	120.4
C6—C7—H7	119.7	C15—C20—C19	120.60 (15)
C8—C7—H7	119.7	C15—C20—H20	119.7
C9—C8—C7	119.60 (15)	C19—C20—H20	119.7
C9—C8—H8	120.2	O3—C21—H21A	109.5
C7—C8—H8	120.2	O3—C21—H21B	109.5
C8—C9—C10	120.63 (15)	H21A—C21—H21B	109.5
C8—C9—H9	119.7	O3—C21—H21C	109.5
C10—C9—H9	119.7	H21A—C21—H21C	109.5
C5—C10—C9	119.30 (14)	H21B—C21—H21C	109.5
C5—C10—H10	120.3

C1—N1—N2—C3	0.61 (16)	N1—C5—C10—C9	179.96 (14)
C5—N1—N2—C3	−177.93 (13)	C8—C9—C10—C5	0.2 (2)
N2—N1—C1—O1	178.89 (14)	C1—C2—C11—O2	−3.6 (2)
C5—N1—C1—O1	−2.8 (3)	C3—C2—C11—O2	176.96 (17)
N2—N1—C1—C2	−0.54 (17)	C1—C2—C11—C12	175.40 (15)
C5—N1—C1—C2	177.79 (15)	C3—C2—C11—C12	−4.1 (3)
O1—C1—C2—C3	−179.15 (15)	O2—C11—C12—C13	7.2 (2)
N1—C1—C2—C3	0.26 (17)	C2—C11—C12—C13	−171.74 (15)
O1—C1—C2—C11	1.2 (2)	C15—N3—C13—C12	169.33 (15)
N1—C1—C2—C11	−179.38 (13)	C15—N3—C13—C14	−12.5 (2)
N1—N2—C3—C2	−0.44 (17)	C11—C12—C13—N3	−1.7 (2)
N1—N2—C3—C4	−179.84 (13)	C11—C12—C13—C14	−179.77 (15)
C1—C2—C3—N2	0.12 (18)	C13—N3—C15—C20	109.16 (18)
C11—C2—C3—N2	179.67 (17)	C13—N3—C15—C16	−74.5 (2)
C1—C2—C3—C4	179.46 (15)	C20—C15—C16—C17	0.7 (2)
C11—C2—C3—C4	−1.0 (3)	N3—C15—C16—C17	−175.75 (13)
C1—N1—C5—C10	−20.5 (2)	C15—C16—C17—C18	−0.3 (2)
N2—N1—C5—C10	157.74 (14)	C21—O3—C18—C19	0.5 (2)
C1—N1—C5—C6	159.97 (15)	C21—O3—C18—C17	−179.53 (13)
N2—N1—C5—C6	−21.8 (2)	C16—C17—C18—O3	179.91 (13)
C10—C5—C6—C7	0.3 (2)	C16—C17—C18—C19	−0.2 (2)
N1—C5—C6—C7	179.88 (14)	O3—C18—C19—C20	−179.88 (13)
C5—C6—C7—C8	0.2 (2)	C17—C18—C19—C20	0.2 (2)
C6—C7—C8—C9	−0.5 (3)	C16—C15—C20—C19	−0.6 (2)
C7—C8—C9—C10	0.3 (3)	N3—C15—C20—C19	175.76 (13)
C6—C5—C10—C9	−0.5 (2)	C18—C19—C20—C15	0.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N1,N2,C1–C3 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.86 (1)	1.68 (1)	2.4963 (15)	156 (2)
N3—H3···O2	0.89 (1)	1.92 (1)	2.6447 (16)	138 (2)
C14—H14b···Cg1ⁱ	0.98	2.88	3.5542 (18)	127
C21—H21c···Cg2ⁱⁱ	0.98	2.76	3.5195 (17)	134

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₁N₃O₃
M_r	363.41
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.5717 (3), 16.9516 (6), 11.3143 (4)
β (°)	104.946 (4)
V (Å³)	1773.70 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.837, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8486, 3939, 3145
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.05
No. of reflections	3939
No. of parameters	255
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)	0.27, −0.23

Computer programs: CrysAlis PRO (Agilent, 2010), 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 N1,N2,C1–C3 and C15–C20 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.864 (10)	1.682 (13)	2.4963 (15)	156 (2)
N3—H3···O2	0.888 (9)	1.918 (14)	2.6447 (16)	137.9 (16)
C14—H14b···Cg1ⁱ	0.98	2.88	3.5542 (18)	127
C21—H21c···Cg2ⁱⁱ	0.98	2.76	3.5195 (17)	134

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

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 at King Abdulaziz University for providing research facilities. Dr Al-Amry is thanked for support. The authors also thank the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, 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
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 67| Part 9| September 2011| Page o2353

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

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Experimental

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organic compounds

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