3,5-Diphenyl-1-(quinolin-2-yl)-4,5-dihydro-1H-pyrazol-5-ol.

In the title compound, C(24)H(19)N(3)O, the pyrazole ring is close to being planar (r.m.s. deviation of the five fitted atoms = 0.062 Å), and each of the N-bound quinoline ring [dihedral angle = 9.90 (7)°] and the C-bound phenyl ring in the 3-position is close to being coplanar [dihedral angle = 8.87 (9)°]. However, the phenyl ring in the 5-position forms a dihedral angle of 72.31 (9)°. The hy-droxy group forms an intra-molecular hydrogen bond to the quinoline N atom. In the crystal, mol-ecules are connected into supra-molecular layers two mol-ecules thick in the bc plane by C-H⋯O and C-H⋯π inter-actions.

Related literature

For applications of coordination complexes of hydrazones as organic light emitting diodes and supra­molecular magnetic clusters, see: Zhang et al. (2011 ▶, 2012 ▶). For the synthesis of hydrazones, see: Gupta et al. (2007 ▶). For background to and the synthesis of the target mol­ecules, see: Najib et al. (2012a ▶,b ▶,c ▶)

Experimental

Crystal data

C24H19N3O

M = 365.42

Monoclinic,

a = 30.505 (2) Å

b = 7.8881 (4) Å

c = 16.5191 (12) Å

β = 113.718 (9)°

V = 3639.1 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.35 × 0.30 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.784, T max = 1.000

12177 measured reflections

4209 independent reflections

3419 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.130

S = 1.07

4209 reflections

257 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 for Windows (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/S1600536812029340/sj5251sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029340/sj5251Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029340/sj5251Isup3.cml

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

C24H19N3O	F(000) = 1536
Mr = 365.42	Dx = 1.334 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4159 reflections
a = 30.505 (2) Å	θ = 2.4–27.5°
b = 7.8881 (4) Å	µ = 0.08 mm−1
c = 16.5191 (12) Å	T = 100 K
β = 113.718 (9)°	Block, yellow
V = 3639.1 (4) Å3	0.35 × 0.30 × 0.25 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	4209 independent reflections
Radiation source: fine-focus sealed tube	3419 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.5°
ω scan	h = −30→39
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −9→10
Tmin = 0.784, Tmax = 1.000	l = −21→14
12177 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0534P)2 + 3.4025P] where P = (Fo2 + 2Fc2)/3
4209 reflections	(Δ/σ)max < 0.001
257 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.32 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	0.43944 (4)	0.27304 (15)	0.51758 (8)	0.0265 (3)
H1o	0.4449 (11)	0.250 (4)	0.5723 (9)	0.087 (11)*
N1	0.40135 (5)	0.26810 (16)	0.64704 (9)	0.0201 (3)
N2	0.36017 (5)	0.33420 (17)	0.50098 (9)	0.0208 (3)
N3	0.32336 (5)	0.29868 (16)	0.42006 (9)	0.0210 (3)
C1	0.40233 (6)	0.20442 (18)	0.72467 (10)	0.0187 (3)
C2	0.44529 (6)	0.2169 (2)	0.80119 (11)	0.0225 (3)
H2	0.4724	0.2708	0.7980	0.027*
C3	0.44810 (6)	0.1519 (2)	0.88010 (11)	0.0241 (4)
H3	0.4772	0.1607	0.9311	0.029*
C4	0.40834 (6)	0.0723 (2)	0.88630 (11)	0.0246 (4)
H4	0.4107	0.0275	0.9413	0.030*
C5	0.36626 (6)	0.05912 (19)	0.81328 (11)	0.0232 (3)
H5	0.3395	0.0054	0.8179	0.028*
C6	0.36217 (6)	0.12429 (18)	0.73125 (10)	0.0195 (3)
C7	0.31958 (6)	0.1126 (2)	0.65227 (11)	0.0218 (3)
H7	0.2921	0.0580	0.6534	0.026*
C8	0.31823 (6)	0.17893 (19)	0.57593 (11)	0.0213 (3)
H8	0.2899	0.1730	0.5232	0.026*
C9	0.36047 (6)	0.25830 (19)	0.57660 (10)	0.0193 (3)
C10	0.40389 (6)	0.3997 (2)	0.49355 (11)	0.0215 (3)
C11	0.38509 (6)	0.4283 (2)	0.39280 (10)	0.0234 (4)
H11A	0.3836	0.5507	0.3786	0.028*
H11B	0.4056	0.3703	0.3677	0.028*
C12	0.33582 (5)	0.35170 (19)	0.35852 (10)	0.0196 (3)
C13	0.42182 (5)	0.56032 (19)	0.54739 (10)	0.0185 (3)
C14	0.47014 (6)	0.6033 (2)	0.57873 (11)	0.0228 (3)
H14	0.4921	0.5291	0.5690	0.027*
C15	0.48632 (6)	0.7545 (2)	0.62411 (12)	0.0275 (4)
H15	0.5192	0.7839	0.6449	0.033*
C16	0.45464 (6)	0.8621 (2)	0.63909 (11)	0.0273 (4)
H16	0.4658	0.9649	0.6706	0.033*
C17	0.40668 (6)	0.8200 (2)	0.60811 (12)	0.0283 (4)
H17	0.3848	0.8937	0.6184	0.034*
C18	0.39055 (6)	0.6704 (2)	0.56208 (11)	0.0245 (4)
H18	0.3575	0.6429	0.5402	0.029*
C19	0.30291 (5)	0.33954 (19)	0.26559 (10)	0.0194 (3)
C20	0.25909 (6)	0.2537 (2)	0.24096 (11)	0.0213 (3)
H20	0.2515	0.1979	0.2846	0.026*
C21	0.22711 (6)	0.2503 (2)	0.15352 (11)	0.0233 (3)
H21	0.1975	0.1919	0.1372	0.028*
C22	0.23785 (6)	0.3313 (2)	0.08928 (11)	0.0240 (3)
H22	0.2154	0.3305	0.0294	0.029*
C23	0.28120 (6)	0.4133 (2)	0.11249 (11)	0.0238 (4)
H23	0.2887	0.4674	0.0682	0.029*
C24	0.31400 (6)	0.4175 (2)	0.20006 (11)	0.0223 (3)
H24	0.3439	0.4731	0.2154	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0252 (6)	0.0256 (6)	0.0271 (7)	0.0021 (5)	0.0087 (5)	−0.0023 (5)
N1	0.0211 (7)	0.0193 (6)	0.0190 (7)	−0.0010 (5)	0.0071 (5)	−0.0013 (5)
N2	0.0180 (6)	0.0245 (7)	0.0171 (6)	−0.0051 (5)	0.0042 (5)	−0.0010 (5)
N3	0.0198 (7)	0.0213 (7)	0.0175 (7)	−0.0006 (5)	0.0031 (5)	−0.0006 (5)
C1	0.0216 (8)	0.0162 (7)	0.0194 (8)	0.0011 (6)	0.0094 (6)	−0.0018 (6)
C2	0.0209 (8)	0.0239 (8)	0.0231 (8)	−0.0005 (6)	0.0094 (6)	−0.0018 (6)
C3	0.0253 (8)	0.0263 (8)	0.0188 (8)	0.0043 (6)	0.0068 (6)	−0.0015 (6)
C4	0.0344 (9)	0.0197 (8)	0.0218 (8)	0.0042 (6)	0.0134 (7)	0.0031 (6)
C5	0.0286 (8)	0.0165 (7)	0.0272 (8)	−0.0003 (6)	0.0140 (7)	0.0001 (6)
C6	0.0229 (8)	0.0140 (7)	0.0232 (8)	0.0012 (6)	0.0108 (6)	−0.0015 (6)
C7	0.0221 (8)	0.0187 (7)	0.0273 (8)	−0.0026 (6)	0.0128 (7)	−0.0016 (6)
C8	0.0189 (7)	0.0198 (7)	0.0233 (8)	−0.0015 (6)	0.0066 (6)	−0.0020 (6)
C9	0.0214 (8)	0.0170 (7)	0.0194 (8)	0.0003 (6)	0.0083 (6)	−0.0009 (6)
C10	0.0210 (8)	0.0222 (8)	0.0217 (8)	−0.0031 (6)	0.0088 (6)	−0.0024 (6)
C11	0.0227 (8)	0.0258 (8)	0.0197 (8)	−0.0047 (6)	0.0065 (6)	−0.0027 (6)
C12	0.0205 (8)	0.0173 (7)	0.0202 (8)	0.0012 (6)	0.0074 (6)	−0.0004 (6)
C13	0.0210 (7)	0.0196 (7)	0.0146 (7)	−0.0023 (6)	0.0067 (6)	0.0003 (6)
C14	0.0199 (8)	0.0245 (8)	0.0239 (8)	−0.0003 (6)	0.0085 (6)	−0.0036 (6)
C15	0.0212 (8)	0.0278 (9)	0.0292 (9)	−0.0051 (7)	0.0057 (7)	−0.0041 (7)
C16	0.0335 (9)	0.0216 (8)	0.0233 (8)	−0.0019 (7)	0.0077 (7)	−0.0040 (6)
C17	0.0310 (9)	0.0256 (9)	0.0308 (9)	0.0052 (7)	0.0150 (7)	−0.0023 (7)
C18	0.0200 (8)	0.0264 (8)	0.0273 (9)	0.0005 (6)	0.0096 (7)	0.0010 (7)
C19	0.0193 (7)	0.0180 (7)	0.0186 (7)	0.0039 (6)	0.0051 (6)	−0.0017 (6)
C20	0.0214 (8)	0.0220 (8)	0.0202 (8)	0.0001 (6)	0.0081 (6)	−0.0006 (6)
C21	0.0182 (8)	0.0256 (8)	0.0245 (8)	−0.0021 (6)	0.0069 (6)	−0.0015 (6)
C22	0.0229 (8)	0.0256 (8)	0.0198 (8)	0.0010 (6)	0.0048 (6)	−0.0010 (6)
C23	0.0260 (8)	0.0249 (8)	0.0207 (8)	−0.0015 (6)	0.0097 (7)	0.0012 (6)
C24	0.0201 (8)	0.0218 (8)	0.0246 (8)	−0.0019 (6)	0.0086 (6)	−0.0020 (6)

O1—C10	1.409 (2)	C11—H11A	0.9900
O1—H1o	0.871 (10)	C11—H11B	0.9900
N1—C9	1.3220 (19)	C12—C19	1.461 (2)
N1—C1	1.366 (2)	C13—C18	1.382 (2)
N2—C9	1.382 (2)	C13—C14	1.393 (2)
N2—N3	1.3850 (17)	C14—C15	1.389 (2)
N2—C10	1.481 (2)	C14—H14	0.9500
N3—C12	1.290 (2)	C15—C16	1.381 (2)
C1—C2	1.411 (2)	C15—H15	0.9500
C1—C6	1.421 (2)	C16—C17	1.382 (2)
C2—C3	1.371 (2)	C16—H16	0.9500
C2—H2	0.9500	C17—C18	1.383 (2)
C3—C4	1.405 (2)	C17—H17	0.9500
C3—H3	0.9500	C18—H18	0.9500
C4—C5	1.367 (2)	C19—C24	1.400 (2)
C4—H4	0.9500	C19—C20	1.405 (2)
C5—C6	1.407 (2)	C20—C21	1.380 (2)
C5—H5	0.9500	C20—H20	0.9500
C6—C7	1.426 (2)	C21—C22	1.386 (2)
C7—C8	1.350 (2)	C21—H21	0.9500
C7—H7	0.9500	C22—C23	1.381 (2)
C8—C9	1.429 (2)	C22—H22	0.9500
C8—H8	0.9500	C23—C24	1.389 (2)
C10—C13	1.518 (2)	C23—H23	0.9500
C10—C11	1.543 (2)	C24—H24	0.9500
C11—C12	1.503 (2)
C10—O1—H1o	104 (2)	C12—C11—H11B	111.1
C9—N1—C1	117.48 (13)	C10—C11—H11B	111.1
C9—N2—N3	119.53 (12)	H11A—C11—H11B	109.1
C9—N2—C10	123.18 (12)	N3—C12—C19	120.74 (14)
N3—N2—C10	113.46 (12)	N3—C12—C11	113.60 (14)
C12—N3—N2	108.27 (13)	C19—C12—C11	125.63 (14)
N1—C1—C2	118.47 (14)	C18—C13—C14	118.91 (14)
N1—C1—C6	122.77 (14)	C18—C13—C10	121.07 (14)
C2—C1—C6	118.76 (14)	C14—C13—C10	119.93 (14)
C3—C2—C1	120.37 (15)	C15—C14—C13	120.18 (15)
C3—C2—H2	119.8	C15—C14—H14	119.9
C1—C2—H2	119.8	C13—C14—H14	119.9
C2—C3—C4	120.71 (15)	C16—C15—C14	120.13 (16)
C2—C3—H3	119.6	C16—C15—H15	119.9
C4—C3—H3	119.6	C14—C15—H15	119.9
C5—C4—C3	120.08 (15)	C15—C16—C17	119.90 (16)
C5—C4—H4	120.0	C15—C16—H16	120.1
C3—C4—H4	120.0	C17—C16—H16	120.1
C4—C5—C6	120.68 (16)	C16—C17—C18	119.89 (16)
C4—C5—H5	119.7	C16—C17—H17	120.1
C6—C5—H5	119.7	C18—C17—H17	120.1
C5—C6—C1	119.40 (14)	C13—C18—C17	120.99 (15)
C5—C6—C7	123.54 (15)	C13—C18—H18	119.5
C1—C6—C7	117.06 (14)	C17—C18—H18	119.5
C8—C7—C6	120.24 (15)	C24—C19—C20	119.05 (14)
C8—C7—H7	119.9	C24—C19—C12	120.41 (14)
C6—C7—H7	119.9	C20—C19—C12	120.51 (15)
C7—C8—C9	118.28 (14)	C21—C20—C19	120.14 (15)
C7—C8—H8	120.9	C21—C20—H20	119.9
C9—C8—H8	120.9	C19—C20—H20	119.9
N1—C9—N2	115.56 (14)	C20—C21—C22	120.45 (15)
N1—C9—C8	124.12 (14)	C20—C21—H21	119.8
N2—C9—C8	120.31 (14)	C22—C21—H21	119.8
O1—C10—N2	110.25 (13)	C23—C22—C21	119.90 (15)
O1—C10—C13	111.82 (12)	C23—C22—H22	120.1
N2—C10—C13	111.52 (13)	C21—C22—H22	120.1
O1—C10—C11	108.52 (13)	C22—C23—C24	120.55 (16)
N2—C10—C11	100.60 (12)	C22—C23—H23	119.7
C13—C10—C11	113.56 (13)	C24—C23—H23	119.7
C12—C11—C10	103.23 (13)	C23—C24—C19	119.88 (15)
C12—C11—H11A	111.1	C23—C24—H24	120.1
C10—C11—H11A	111.1	C19—C24—H24	120.1
C9—N2—N3—C12	−165.92 (14)	N2—C10—C11—C12	−7.55 (15)
C10—N2—N3—C12	−7.26 (17)	C13—C10—C11—C12	−126.82 (14)
C9—N1—C1—C2	−178.59 (14)	N2—N3—C12—C19	−176.76 (13)
C9—N1—C1—C6	2.3 (2)	N2—N3—C12—C11	1.48 (18)
N1—C1—C2—C3	−178.78 (14)	C10—C11—C12—N3	4.29 (18)
C6—C1—C2—C3	0.4 (2)	C10—C11—C12—C19	−177.58 (14)
C1—C2—C3—C4	−0.2 (2)	O1—C10—C13—C18	−153.52 (15)
C2—C3—C4—C5	−0.1 (2)	N2—C10—C13—C18	−29.6 (2)
C3—C4—C5—C6	0.2 (2)	C11—C10—C13—C18	83.26 (19)
C4—C5—C6—C1	0.0 (2)	O1—C10—C13—C14	30.0 (2)
C4—C5—C6—C7	179.05 (15)	N2—C10—C13—C14	153.99 (14)
N1—C1—C6—C5	178.84 (14)	C11—C10—C13—C14	−93.20 (18)
C2—C1—C6—C5	−0.3 (2)	C18—C13—C14—C15	0.1 (2)
N1—C1—C6—C7	−0.3 (2)	C10—C13—C14—C15	176.68 (15)
C2—C1—C6—C7	−179.38 (14)	C13—C14—C15—C16	0.6 (3)
C5—C6—C7—C8	179.68 (15)	C14—C15—C16—C17	−0.6 (3)
C1—C6—C7—C8	−1.3 (2)	C15—C16—C17—C18	−0.1 (3)
C6—C7—C8—C9	0.7 (2)	C14—C13—C18—C17	−0.9 (2)
C1—N1—C9—N2	175.86 (13)	C10—C13—C18—C17	−177.38 (15)
C1—N1—C9—C8	−2.9 (2)	C16—C17—C18—C13	0.9 (3)
N3—N2—C9—N1	165.54 (13)	N3—C12—C19—C24	171.36 (14)
C10—N2—C9—N1	9.0 (2)	C11—C12—C19—C24	−6.6 (2)
N3—N2—C9—C8	−15.6 (2)	N3—C12—C19—C20	−6.8 (2)
C10—N2—C9—C8	−172.13 (14)	C11—C12—C19—C20	175.19 (15)
C7—C8—C9—N1	1.5 (2)	C24—C19—C20—C21	−1.5 (2)
C7—C8—C9—N2	−177.26 (14)	C12—C19—C20—C21	176.65 (15)
C9—N2—C10—O1	52.69 (19)	C19—C20—C21—C22	0.0 (2)
N3—N2—C10—O1	−105.08 (14)	C20—C21—C22—C23	1.3 (3)
C9—N2—C10—C13	−72.15 (18)	C21—C22—C23—C24	−0.9 (3)
N3—N2—C10—C13	130.07 (13)	C22—C23—C24—C19	−0.7 (2)
C9—N2—C10—C11	167.12 (14)	C20—C19—C24—C23	1.9 (2)
N3—N2—C10—C11	9.34 (16)	C12—C19—C24—C23	−176.29 (14)
O1—C10—C11—C12	108.17 (14)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1o···N1	0.87 (1)	2.15 (2)	2.8149 (19)	133 (3)
C3—H3···O1i	0.95	2.50	3.298 (2)	142
C11—H11A···Cg1ii	0.99	2.92	3.8528 (18)	157
C17—H17···Cg2iii	0.95	2.58	3.4426 (18)	151
C24—H24···Cg2ii	0.95	2.97	3.6239 (18)	127

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and N1,C1,C6–C9 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1o⋯N1	0.87 (1)	2.15 (2)	2.8149 (19)	133 (3)
C3—H3⋯O1i	0.95	2.50	3.298 (2)	142
C11—H11A⋯Cg1ii	0.99	2.92	3.8528 (18)	157
C17—H17⋯Cg2iii	0.95	2.58	3.4426 (18)	151
C24—H24⋯Cg2ii	0.95	2.97	3.6239 (18)	127

Symmetry codes: (i) ; (ii) ; (iii) .