(2Z)-1-(5-Hy-droxy-3-methyl-1-phenyl-1H-pyrazol-4-yl)-3-(4-meth-oxy-anilino)but-2-en-1-one.

The central residue in the title compound, C(21)H(21)N(3)O(3), is close to planar (r.m.s. deviation = 0.0753 Å for all non-H atoms from OH to NH inclusive): the hy-droxy, amino and carbonyl groups all lie to the same side of the mol-ecule (the conformation about the ethene bond is Z), facilitating the formation of intra-molecular O-H⋯O and N-H⋯O hydrogen bonds that close S(6) rings. However, overall the mol-ecule 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 meth-oxy-benzene ring, respectively]. The dihedral angle between the rings is 82.14 (7)°. Supra-molecular layers in the ac plane mediated by C-H⋯π inter-actions 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 = 363.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.104

S = 1.05

3939 reflections

255 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.23 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032491/hb6355sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811032491/hb6355Isup3.cml

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

C21H21N3O3	F(000) = 768
Mr = 363.41	Dx = 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

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	Rint = 0.024
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.4°
ω scans	h = −12→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −17→21
Tmin = 0.837, Tmax = 1.000	l = −14→14
8486 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)] = 0.042	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(Fo2) + (0.0364P)2 + 0.8331P] where P = (Fo2 + 2Fc2)/3
3939 reflections	(Δ/σ)max < 0.001
255 parameters	Δρmax = 0.27 e Å−3
2 restraints	Δρmin = −0.23 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
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)*

	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)

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)

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

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) ; (ii) .