2-{5-[2-(4-Nitro-phen-oxy)phen-yl]-1-phenyl-1H-pyrazol-3-yl}phenol.

In the title compound, C(27)H(19)N(3)O(4), the phenol and pyrazole rings are almost coplanar [dihedral angle = 0.95 (12)°] due to an intra-molecular O-H⋯N hydrogen bond, whereas the phenyl ring is tilted by 40.81 (7)° with respect to the plane of the pyrazole ring. The aromatic ring with a nitro-phen-oxy substituent makes a dihedral angle of 54.10 (7)° with the pyrazole ring.

Related literature

For pyrazole-containing derivatives, see: Habeeb et al. (2001 ▶); Hashimoto et al. (2002 ▶); Ranatunge et al. (2004 ▶); Elzein et al. (2006 ▶); Singh et al. (2005 ▶). For the properties and applications of aromatic polymers with diazole rings in the main chain, see: Bruma et al. (2003 ▶); Sava et al. (2003 ▶, 2006 ▶); Schulz et al. (1997 ▶). For the preparation of 2-(3-(2-hydroxy­phen­yl)-1-phenyl-1H-pyrazol-5-yl)phenol, see: Mukherjee (2000 ▶).

Experimental

Crystal data

C27H19N3O4

M = 449.45

Monoclinic,

a = 12.1361 (12) Å

b = 10.9072 (12) Å

c = 16.6380 (16) Å

β = 98.081 (8)°

V = 2180.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.32 × 0.31 × 0.28 mm

Data collection

Stoe IPDS II two-circle diffractometer

12421 measured reflections

4064 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.076

S = 0.81

4064 reflections

312 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810008251/kp2252sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008251/kp2252Isup2.hkl

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

C27H19N3O4	F(000) = 936
Mr = 449.45	Dx = 1.369 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6595 reflections
a = 12.1361 (12) Å	θ = 3.4–26.0°
b = 10.9072 (12) Å	µ = 0.09 mm−1
c = 16.6380 (16) Å	T = 173 K
β = 98.081 (8)°	Block, colourless
V = 2180.5 (4) Å3	0.32 × 0.31 × 0.28 mm
Z = 4

Stoe IPDS II two-circle diffractometer	2486 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.057
graphite	θmax = 25.6°, θmin = 3.4°
ω scans	h = −14→14
12421 measured reflections	k = −11→13
4064 independent reflections	l = −20→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.076	w = 1/[σ2(Fo2) + (0.0294P)2] where P = (Fo2 + 2Fc2)/3
S = 0.81	(Δ/σ)max < 0.001
4064 reflections	Δρmax = 0.16 e Å−3
312 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0067 (5)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.65535 (10)	0.61876 (14)	0.45161 (9)	0.0274 (3)
N2	0.57870 (10)	0.70777 (14)	0.42624 (9)	0.0286 (4)
N3	1.03923 (12)	1.04191 (16)	0.68913 (12)	0.0408 (4)
C3	0.53351 (12)	0.73920 (17)	0.49247 (11)	0.0278 (4)
C4	0.58124 (12)	0.67048 (18)	0.56011 (11)	0.0306 (4)
H4	0.5634	0.6751	0.6138	0.037*
C5	0.65914 (12)	0.59517 (17)	0.53256 (11)	0.0273 (4)
O1	0.89602 (9)	0.60627 (12)	0.53359 (7)	0.0312 (3)
O2	0.44973 (10)	0.86574 (14)	0.34163 (8)	0.0376 (3)
H2	0.5028 (18)	0.808 (2)	0.3516 (15)	0.067 (8)*
O3	1.00823 (12)	1.06753 (14)	0.75453 (10)	0.0531 (4)
O4	1.09471 (11)	1.11286 (14)	0.65330 (10)	0.0533 (4)
C11	0.71384 (12)	0.56211 (17)	0.39239 (11)	0.0272 (4)
C12	0.75161 (13)	0.63578 (18)	0.33421 (11)	0.0315 (4)
H12	0.7398	0.7219	0.3341	0.038*
C13	0.80707 (13)	0.5813 (2)	0.27611 (12)	0.0378 (5)
H13	0.8323	0.6304	0.2352	0.045*
C14	0.82606 (14)	0.4566 (2)	0.27703 (12)	0.0408 (5)
H14	0.8650	0.4205	0.2373	0.049*
C15	0.78832 (14)	0.3838 (2)	0.33594 (12)	0.0382 (5)
H15	0.8018	0.2980	0.3367	0.046*
C16	0.73091 (13)	0.43615 (18)	0.39379 (12)	0.0326 (4)
H16	0.7037	0.3866	0.4337	0.039*
C21	0.73660 (12)	0.50662 (17)	0.57734 (11)	0.0280 (4)
C22	0.85183 (13)	0.51311 (17)	0.57759 (11)	0.0277 (4)
C23	0.92304 (14)	0.42891 (18)	0.61848 (12)	0.0341 (5)
H23	1.0006	0.4333	0.6156	0.041*
C24	0.88194 (15)	0.33786 (19)	0.66389 (13)	0.0392 (5)
H24	0.9311	0.2803	0.6930	0.047*
C25	0.76912 (15)	0.33115 (19)	0.66670 (13)	0.0388 (5)
H25	0.7406	0.2693	0.6983	0.047*
C26	0.69702 (14)	0.41432 (18)	0.62353 (12)	0.0335 (5)
H26	0.6194	0.4082	0.6255	0.040*
C31	0.93323 (12)	0.70939 (17)	0.57673 (11)	0.0274 (4)
C32	0.91071 (14)	0.73406 (18)	0.65426 (12)	0.0341 (5)
H32	0.8705	0.6767	0.6818	0.041*
C33	0.94728 (14)	0.84307 (19)	0.69138 (12)	0.0382 (5)
H33	0.9312	0.8618	0.7443	0.046*
C34	1.00691 (13)	0.92394 (17)	0.65128 (12)	0.0318 (4)
C35	1.03368 (13)	0.89819 (18)	0.57519 (12)	0.0335 (5)
H35	1.0774	0.9539	0.5492	0.040*
C36	0.99614 (13)	0.79031 (18)	0.53732 (12)	0.0317 (4)
H36	1.0132	0.7715	0.4847	0.038*
C41	0.44668 (12)	0.83512 (17)	0.48557 (11)	0.0284 (4)
C42	0.40952 (13)	0.89354 (18)	0.41212 (11)	0.0304 (4)
C43	0.32725 (13)	0.98405 (19)	0.40739 (12)	0.0367 (5)
H43	0.3022	1.0227	0.3569	0.044*
C44	0.28269 (14)	1.01707 (19)	0.47573 (13)	0.0396 (5)
H44	0.2267	1.0785	0.4724	0.047*
C45	0.31869 (13)	0.96169 (19)	0.54894 (13)	0.0384 (5)
H45	0.2881	0.9855	0.5961	0.046*
C46	0.39962 (13)	0.87122 (18)	0.55412 (12)	0.0347 (5)
H46	0.4235	0.8331	0.6049	0.042*

	U11	U22	U33	U12	U13	U23
N1	0.0278 (7)	0.0289 (9)	0.0260 (9)	0.0040 (6)	0.0051 (6)	0.0014 (7)
N2	0.0287 (7)	0.0283 (9)	0.0292 (9)	0.0042 (6)	0.0050 (6)	−0.0002 (7)
N3	0.0400 (8)	0.0317 (10)	0.0474 (12)	−0.0007 (7)	−0.0058 (8)	0.0061 (9)
C3	0.0255 (8)	0.0306 (11)	0.0285 (11)	−0.0022 (7)	0.0074 (7)	−0.0023 (9)
C4	0.0299 (8)	0.0367 (12)	0.0262 (10)	−0.0001 (8)	0.0078 (7)	−0.0001 (9)
C5	0.0284 (8)	0.0276 (11)	0.0261 (10)	−0.0017 (7)	0.0051 (7)	0.0025 (8)
O1	0.0335 (6)	0.0338 (8)	0.0273 (7)	−0.0074 (5)	0.0080 (5)	−0.0027 (6)
O2	0.0424 (7)	0.0438 (9)	0.0278 (8)	0.0089 (6)	0.0094 (6)	0.0037 (7)
O3	0.0711 (9)	0.0403 (10)	0.0465 (10)	−0.0033 (7)	0.0033 (8)	−0.0080 (8)
O4	0.0550 (8)	0.0366 (9)	0.0659 (11)	−0.0147 (7)	0.0001 (7)	0.0073 (9)
C11	0.0250 (8)	0.0314 (11)	0.0249 (10)	0.0014 (7)	0.0027 (7)	−0.0039 (9)
C12	0.0312 (8)	0.0327 (11)	0.0312 (11)	0.0015 (8)	0.0067 (7)	0.0015 (10)
C13	0.0346 (9)	0.0493 (14)	0.0304 (12)	0.0051 (9)	0.0084 (8)	0.0015 (10)
C14	0.0342 (9)	0.0555 (15)	0.0319 (12)	0.0109 (9)	0.0024 (8)	−0.0108 (11)
C15	0.0401 (9)	0.0345 (12)	0.0375 (12)	0.0094 (8)	−0.0029 (8)	−0.0119 (11)
C16	0.0350 (9)	0.0294 (11)	0.0321 (11)	−0.0003 (8)	0.0007 (8)	−0.0008 (9)
C21	0.0307 (8)	0.0279 (11)	0.0257 (10)	−0.0016 (7)	0.0045 (7)	−0.0026 (9)
C22	0.0314 (8)	0.0260 (11)	0.0261 (10)	−0.0037 (7)	0.0056 (7)	−0.0031 (9)
C23	0.0328 (9)	0.0341 (12)	0.0347 (11)	0.0042 (8)	0.0017 (8)	−0.0027 (10)
C24	0.0428 (10)	0.0316 (12)	0.0409 (12)	0.0069 (9)	−0.0019 (8)	0.0017 (10)
C25	0.0495 (11)	0.0294 (11)	0.0369 (12)	−0.0049 (9)	0.0043 (9)	0.0077 (10)
C26	0.0340 (9)	0.0324 (12)	0.0343 (11)	−0.0050 (8)	0.0055 (8)	0.0017 (10)
C31	0.0238 (8)	0.0289 (11)	0.0292 (11)	0.0013 (7)	0.0022 (7)	−0.0009 (9)
C32	0.0402 (9)	0.0333 (12)	0.0304 (11)	−0.0071 (8)	0.0101 (8)	0.0012 (10)
C33	0.0492 (10)	0.0362 (12)	0.0300 (11)	−0.0045 (9)	0.0088 (9)	−0.0014 (10)
C34	0.0315 (8)	0.0259 (11)	0.0355 (11)	−0.0016 (7)	−0.0035 (8)	0.0025 (9)
C35	0.0280 (8)	0.0317 (12)	0.0414 (12)	−0.0018 (8)	0.0067 (8)	0.0081 (10)
C36	0.0303 (9)	0.0349 (12)	0.0312 (11)	0.0010 (8)	0.0093 (8)	0.0051 (10)
C41	0.0260 (8)	0.0300 (11)	0.0298 (11)	−0.0007 (7)	0.0066 (7)	−0.0027 (9)
C42	0.0293 (8)	0.0317 (11)	0.0311 (11)	−0.0014 (8)	0.0070 (7)	−0.0029 (9)
C43	0.0338 (9)	0.0385 (13)	0.0376 (12)	0.0047 (8)	0.0047 (8)	0.0024 (10)
C44	0.0279 (8)	0.0406 (13)	0.0502 (14)	0.0061 (8)	0.0052 (8)	−0.0034 (11)
C45	0.0305 (9)	0.0474 (14)	0.0394 (12)	0.0030 (8)	0.0119 (8)	−0.0093 (11)
C46	0.0317 (8)	0.0428 (13)	0.0302 (11)	0.0009 (8)	0.0064 (7)	−0.0016 (10)

N1—C5	1.366 (2)	C22—C23	1.374 (3)
N1—N2	1.370 (2)	C23—C24	1.383 (3)
N1—C11	1.433 (2)	C23—H23	0.9500
N2—C3	1.343 (2)	C24—C25	1.378 (3)
N3—O3	1.232 (2)	C24—H24	0.9500
N3—O4	1.233 (2)	C25—C26	1.388 (3)
N3—C34	1.462 (3)	C25—H25	0.9500
C3—C4	1.407 (3)	C26—H26	0.9500
C3—C41	1.478 (2)	C31—C32	1.382 (3)
C4—C5	1.379 (2)	C31—C36	1.390 (2)
C4—H4	0.9500	C32—C33	1.384 (3)
C5—C21	1.475 (2)	C32—H32	0.9500
O1—C31	1.376 (2)	C33—C34	1.372 (3)
O1—C22	1.402 (2)	C33—H33	0.9500
O2—C42	1.366 (2)	C34—C35	1.379 (3)
O2—H2	0.90 (2)	C35—C36	1.381 (3)
C11—C12	1.385 (3)	C35—H35	0.9500
C11—C16	1.389 (3)	C36—H36	0.9500
C12—C13	1.387 (3)	C41—C42	1.396 (3)
C12—H12	0.9500	C41—C46	1.402 (2)
C13—C14	1.380 (3)	C42—C43	1.398 (3)
C13—H13	0.9500	C43—C44	1.374 (3)
C14—C15	1.388 (3)	C43—H43	0.9500
C14—H14	0.9500	C44—C45	1.375 (3)
C15—C16	1.388 (3)	C44—H44	0.9500
C15—H15	0.9500	C45—C46	1.386 (3)
C16—H16	0.9500	C45—H45	0.9500
C21—C26	1.392 (3)	C46—H46	0.9500
C21—C22	1.400 (2)
C5—N1—N2	111.39 (14)	C25—C24—C23	119.53 (18)
C5—N1—C11	130.22 (15)	C25—C24—H24	120.2
N2—N1—C11	118.32 (14)	C23—C24—H24	120.2
C3—N2—N1	105.44 (15)	C24—C25—C26	120.30 (19)
O3—N3—O4	122.67 (18)	C24—C25—H25	119.9
O3—N3—C34	118.89 (17)	C26—C25—H25	119.9
O4—N3—C34	118.42 (18)	C25—C26—C21	121.11 (16)
N2—C3—C4	110.53 (15)	C25—C26—H26	119.4
N2—C3—C41	119.08 (17)	C21—C26—H26	119.4
C4—C3—C41	130.39 (16)	O1—C31—C32	123.54 (16)
C5—C4—C3	106.01 (15)	O1—C31—C36	115.77 (16)
C5—C4—H4	127.0	C32—C31—C36	120.69 (17)
C3—C4—H4	127.0	C31—C32—C33	119.39 (18)
N1—C5—C4	106.63 (15)	C31—C32—H32	120.3
N1—C5—C21	123.53 (15)	C33—C32—H32	120.3
C4—C5—C21	129.83 (16)	C34—C33—C32	119.56 (18)
C31—O1—C22	116.21 (13)	C34—C33—H33	120.2
C42—O2—H2	109.2 (16)	C32—C33—H33	120.2
C12—C11—C16	121.49 (17)	C33—C34—C35	121.58 (18)
C12—C11—N1	118.36 (16)	C33—C34—N3	118.97 (18)
C16—C11—N1	120.14 (17)	C35—C34—N3	119.41 (17)
C11—C12—C13	118.65 (18)	C34—C35—C36	119.14 (17)
C11—C12—H12	120.7	C34—C35—H35	120.4
C13—C12—H12	120.7	C36—C35—H35	120.4
C14—C13—C12	120.76 (19)	C35—C36—C31	119.57 (17)
C14—C13—H13	119.6	C35—C36—H36	120.2
C12—C13—H13	119.6	C31—C36—H36	120.2
C13—C14—C15	120.03 (18)	C42—C41—C46	117.76 (16)
C13—C14—H14	120.0	C42—C41—C3	122.02 (16)
C15—C14—H14	120.0	C46—C41—C3	120.22 (17)
C16—C15—C14	120.2 (2)	O2—C42—C41	122.68 (16)
C16—C15—H15	119.9	O2—C42—C43	116.53 (17)
C14—C15—H15	119.9	C41—C42—C43	120.79 (17)
C15—C16—C11	118.91 (19)	C44—C43—C42	119.95 (19)
C15—C16—H16	120.5	C44—C43—H43	120.0
C11—C16—H16	120.5	C42—C43—H43	120.0
C26—C21—C22	117.19 (16)	C43—C44—C45	120.34 (18)
C26—C21—C5	120.50 (14)	C43—C44—H44	119.8
C22—C21—C5	122.28 (16)	C45—C44—H44	119.8
C23—C22—C21	121.75 (17)	C44—C45—C46	120.14 (18)
C23—C22—O1	118.87 (14)	C44—C45—H45	119.9
C21—C22—O1	119.37 (15)	C46—C45—H45	119.9
C22—C23—C24	120.04 (16)	C45—C46—C41	121.02 (18)
C22—C23—H23	120.0	C45—C46—H46	119.5
C24—C23—H23	120.0	C41—C46—H46	119.5
C5—N1—N2—C3	−0.50 (19)	C22—C23—C24—C25	1.0 (3)
C11—N1—N2—C3	176.84 (14)	C23—C24—C25—C26	0.7 (3)
N1—N2—C3—C4	0.04 (19)	C24—C25—C26—C21	−0.6 (3)
N1—N2—C3—C41	179.75 (15)	C22—C21—C26—C25	−1.1 (3)
N2—C3—C4—C5	0.4 (2)	C5—C21—C26—C25	−179.30 (18)
C41—C3—C4—C5	−179.25 (18)	C22—O1—C31—C32	−12.3 (2)
N2—N1—C5—C4	0.76 (19)	C22—O1—C31—C36	167.88 (15)
C11—N1—C5—C4	−176.16 (16)	O1—C31—C32—C33	−176.95 (16)
N2—N1—C5—C21	−177.86 (15)	C36—C31—C32—C33	2.8 (3)
C11—N1—C5—C21	5.2 (3)	C31—C32—C33—C34	−1.1 (3)
C3—C4—C5—N1	−0.69 (19)	C32—C33—C34—C35	−1.5 (3)
C3—C4—C5—C21	177.80 (17)	C32—C33—C34—N3	176.35 (16)
C5—N1—C11—C12	−141.18 (18)	O3—N3—C34—C33	−2.9 (2)
N2—N1—C11—C12	42.1 (2)	O4—N3—C34—C33	178.57 (17)
C5—N1—C11—C16	39.2 (3)	O3—N3—C34—C35	174.99 (17)
N2—N1—C11—C16	−137.50 (16)	O4—N3—C34—C35	−3.6 (2)
C16—C11—C12—C13	0.4 (3)	C33—C34—C35—C36	2.3 (3)
N1—C11—C12—C13	−179.21 (15)	N3—C34—C35—C36	−175.46 (15)
C11—C12—C13—C14	−1.2 (3)	C34—C35—C36—C31	−0.6 (2)
C12—C13—C14—C15	0.8 (3)	O1—C31—C36—C35	177.84 (14)
C13—C14—C15—C16	0.3 (3)	C32—C31—C36—C35	−1.9 (3)
C14—C15—C16—C11	−1.1 (3)	N2—C3—C41—C42	0.5 (3)
C12—C11—C16—C15	0.8 (3)	C4—C3—C41—C42	−179.89 (18)
N1—C11—C16—C15	−179.68 (15)	N2—C3—C41—C46	−178.83 (16)
N1—C5—C21—C26	−127.17 (19)	C4—C3—C41—C46	0.8 (3)
C4—C5—C21—C26	54.6 (3)	C46—C41—C42—O2	179.91 (16)
N1—C5—C21—C22	54.8 (3)	C3—C41—C42—O2	0.6 (3)
C4—C5—C21—C22	−123.5 (2)	C46—C41—C42—C43	−0.7 (3)
C26—C21—C22—C23	2.9 (3)	C3—C41—C42—C43	−179.97 (17)
C5—C21—C22—C23	−178.94 (18)	O2—C42—C43—C44	180.00 (17)
C26—C21—C22—O1	−178.47 (16)	C41—C42—C43—C44	0.5 (3)
C5—C21—C22—O1	−0.4 (3)	C42—C43—C44—C45	0.1 (3)
C31—O1—C22—C23	−85.43 (19)	C43—C44—C45—C46	−0.6 (3)
C31—O1—C22—C21	95.94 (18)	C44—C45—C46—C41	0.5 (3)
C21—C22—C23—C24	−2.9 (3)	C42—C41—C46—C45	0.2 (3)
O1—C22—C23—C24	178.47 (17)	C3—C41—C46—C45	179.50 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.90 (2)	1.81 (3)	2.604 (2)	146 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.90 (2)	1.81 (3)	2.604 (2)	146 (2)