organic compounds
2-{5-[2-(4-Nitrophenoxy)phenyl]-1-phenyl-1H-pyrazol-3-yl}phenol
aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, bInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany, and cNational Engineering and Scientific Commission, PO Box 2216, Islamabad, Pakistan
*Correspondence e-mail: zareenakhter@yahoo.com
In the title compound, C27H19N3O4, the phenol and pyrazole rings are almost coplanar [dihedral angle = 0.95 (12)°] due to an intramolecular 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 nitrophenoxy 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
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Data collection
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2001); cell 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.
Supporting information
10.1107/S1600536810008251/kp2252sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810008251/kp2252Isup2.hkl
A mixture of 0.961 g (0.0061 mol) of 4- nitrophenol, 2 g (0.0061 mol) of synthesized 2-(3-(2-hydroxyphenyl)-1-phenyl-1H-pyrazol-5-yl)phenol (Mukherjee, 2000) and 0.842 g (0.0061 mol) of potassium carbonate in 50 ml of DMF was heated with stirring at 393 K for 12 h. The reaction mixture was cooled to room temperature and poured into 800 ml of ice cold water which resulted the yellow precipitation. After being washed repeatedly with water, the product was collected by filtration and was recrystallized from DMF to yield 72% of product (m.p. 474 K).
Hydrogen atoms bonded to C were included in calculated positions [C—H = 0.95 Å] and refined as riding [Uiso(H) = 1.2Ueq(C)]. The hydroxyl H atom was freely refined.
Data collection: X-AREA (Stoe & Cie, 2001); cell
X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).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 monochromator | 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) |
C27H19N3O4 | V = 2180.5 (4) Å3 |
Mr = 449.45 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 12.1361 (12) Å | µ = 0.09 mm−1 |
b = 10.9072 (12) Å | T = 173 K |
c = 16.6380 (16) Å | 0.32 × 0.31 × 0.28 mm |
β = 98.081 (8)° |
Stoe IPDS II two-circle diffractometer | 2486 reflections with I > 2σ(I) |
12421 measured reflections | Rint = 0.057 |
4064 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.81 | Δρmax = 0.16 e Å−3 |
4064 reflections | Δρmin = −0.15 e Å−3 |
312 parameters |
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) |
Experimental details
Crystal data | |
Chemical formula | C27H19N3O4 |
Mr | 449.45 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 12.1361 (12), 10.9072 (12), 16.6380 (16) |
β (°) | 98.081 (8) |
V (Å3) | 2180.5 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.32 × 0.31 × 0.28 |
Data collection | |
Diffractometer | Stoe IPDS II two-circle diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12421, 4064, 2486 |
Rint | 0.057 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.076, 0.81 |
No. of reflections | 4064 |
No. of parameters | 312 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.15 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008).
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) |
Acknowledgements
The authors are grateful to the Department of Chemistry, Quaid-I-Azam University, Islamabad, and the Institute for Inorganic Chemistry, University of Frankfurt, for providing laboratory and analytical facilities. The authors are also grateful to the Higher Education Commission of Pakistan for financial support through Project No. 20–723/R&D/06/191.
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Pyrazole containing derivatives are attracted attention due to their biological properties and their outstanding functions as a part of aromatic polymer chains. The pyrazole unit is one of the core structures in a number of natural products and has been attracted attention in the field of biology (Habeeb et al., 2001, Hashimoto et al. 2002). Extensive studies have been devoted to arylpyrazole derivatives such as celecoxib,a well-known cyclooxygenase-2 inhibitor (Ranatunge et al., 2004; Singh et al. 2005). Recently, pyrazole derivatives have been reported as high affinity and selective A2B adenosine receptor antagonist (Elzein et al., 2006). On the other hand, it was shown that aromatic polymer with diazole rings in the main chain exhibit high thermal resistance in oxidative atmosphere, good hydrolytic stability, low dielectric permittivity, high toughness and other special properties which are determined by the electronic structure of this particular heterocycle (Schulz et al., 1997; Sava et al., 2003). The incorporation of oxadiazole and imide rings together with flexible groups into the polymer chain is expected to provide a combination of high-performance properties and processability (Bruma et al., 2003, Sava et al., 2006). The title compound, 2-(5-(2-(4-nitrophenoxy)phenyl)-1-phenyl-1H-pyrazol-3-yl)phenol has the prerequisite arylether linkages along with the hydroxyl and nitro-moieties and therefore can be an attractive synthon in material for biological application.
The o-phenol ring and the pyrazole ring in the title compound are almost coplanar [dihedral angle 0.95 (12)°] due to an intramolecular hydrogen bond, whereas the phenyl ring is tilted by 40.81 (7)° to the pyrazole ring. The aromatic ring carrying the nitrophenoxy substitutent makes a dihedral angle of 54.10 (7)° with the pyrazol ring. Crystal packing is determined by van der Waals interactions.