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

A twist is evident in the title compound, C(21)H(21)N(3)O(2), 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 intra-molecular hydrogen bonds from the adjacent hy-droxy and amine groups. The three-dimensional crystal packing is achieved through C-H⋯π inter-actions.

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 = 347.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.164

S = 1.02

4055 reflections

246 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.24 e Å−3

Δρmin = −0.29 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006526/hg5179sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812006526/hg5179Isup3.cml

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

C21H21N3O2	F(000) = 736
Mr = 347.41	Dx = 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

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	Rint = 0.076
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.4°
ω scan	h = −18→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −8→8
Tmin = 0.967, Tmax = 0.998	l = −22→18
12780 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)] = 0.060	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(Fo2) + (0.065P)2 + 0.099P] where P = (Fo2 + 2Fc2)/3
4055 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.24 e Å−3
2 restraints	Δρmin = −0.29 e Å−3

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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

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) ; (ii) ; (iii) , .