The title compound, C
21H
16N
2O
2, was derived from 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione. The pyrazole ring and one of the hydroxy-substituted benzene rings are approximately coplanar, forming a dihedral angle of 7.5 (3)°. The relative conformation of these rings may be influenced by an intramolecular O—H

N hydrogen bond. In the crystal structure, intermolecular O—H

O hydrogen bonds involving different hydroxy groups of symmetry-related molecules form extended chains along [201].
Supporting information
CCDC reference: 696537
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.047
- wR factor = 0.129
- Data-to-parameter ratio = 16.4
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 300 Ang.
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
0 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
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Compound (I) [see Fig. 3] was prepared by a modified Baker Venkataram
rearrangement as
reported earlier (Ahmad et al., 1990, 1997). Purification was
carried
out by recrystallization using absolute ethanol. Compound (II) was synthesized
by adding 0.1 mole of phenyl hydrazine in 0.1 mole of compound (II) dissolved
in 200 ml of absolute ethanol. The mixture was refluxed for 7 h. Solvent was
removed under reduced pressure. Highly viscous residue was recrystallized
using absolute ethanol. Compound (III) was synthesized by demethylation of
compound (II) using 48% hydrogen bromide in acetic acid. Single crystals
suitable for X-ray analysis were obtained by recrystallization from
an ethanol solution of (III) at room temperature (Yield: 96%, m.p: 490K).
All H atoms were placed in idealized positions and treated as riding
atoms, with C—H = 0.93Å, O-H = 0.82Å and
Uiso(H) = 1.2Ueq(C) or 1.5Ueq(O).
Data collection: XSCANS (Siemens, 1999); cell refinement: XSCANS (Siemens, 1999); data reduction: XSCANS (Siemens, 1999); program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008); program(s) used to refine structure: SHELXTL-Plus (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).
2-[5-(4-Hydroxyphenyl)-1-phenyl-1
H-pyrazol-3-yl]phenol
top
Crystal data top
C21H16N2O2 | F(000) = 688 |
Mr = 328.36 | Dx = 1.336 Mg m−3 |
Monoclinic, P21/c | Melting point: 490 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 10.793 (3) Å | Cell parameters from 84 reflections |
b = 12.948 (3) Å | θ = 4.6–12.4° |
c = 11.705 (3) Å | µ = 0.09 mm−1 |
β = 93.508 (14)° | T = 298 K |
V = 1632.7 (7) Å3 | Prismatic, colourless |
Z = 4 | 0.44 × 0.40 × 0.26 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.024 |
Radiation source: fine-focus sealed tube | θmax = 27.5°, θmin = 1.9° |
Graphite monochromator | h = −14→4 |
2θ/ω scans | k = −16→1 |
5767 measured reflections | l = −15→15 |
3720 independent reflections | 3 standard reflections every 97 reflections |
2353 reflections with I > 2σ(I) | intensity decay: 3.7% |
Refinement top
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)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.0468P)2 + 0.4416P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3720 reflections | Δρmax = 0.15 e Å−3 |
227 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXTL-Plus (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0155 (18) |
Crystal data top
C21H16N2O2 | V = 1632.7 (7) Å3 |
Mr = 328.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.793 (3) Å | µ = 0.09 mm−1 |
b = 12.948 (3) Å | T = 298 K |
c = 11.705 (3) Å | 0.44 × 0.40 × 0.26 mm |
β = 93.508 (14)° | |
Data collection top
Siemens P4 diffractometer | Rint = 0.024 |
5767 measured reflections | 3 standard reflections every 97 reflections |
3720 independent reflections | intensity decay: 3.7% |
2353 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.15 e Å−3 |
3720 reflections | Δρmin = −0.16 e Å−3 |
227 parameters | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | −0.19429 (12) | 0.33852 (11) | −0.38082 (11) | 0.0598 (4) | |
H1B | −0.2627 | 0.3197 | −0.3621 | 0.090* | |
O2 | 0.55378 (12) | 0.16872 (10) | 0.17109 (13) | 0.0603 (4) | |
H2B | 0.5054 | 0.2064 | 0.1339 | 0.090* | |
N1 | 0.26395 (13) | 0.27005 (12) | −0.01205 (13) | 0.0467 (4) | |
N2 | 0.34918 (13) | 0.21948 (12) | 0.05691 (13) | 0.0462 (4) | |
C1 | 0.3431 (2) | 0.43942 (17) | −0.05478 (19) | 0.0628 (6) | |
H1A | 0.4075 | 0.4086 | −0.0915 | 0.075* | |
C2 | 0.3343 (3) | 0.54518 (19) | −0.0493 (2) | 0.0775 (7) | |
H2A | 0.3933 | 0.5863 | −0.0821 | 0.093* | |
C3 | 0.2391 (2) | 0.58993 (18) | 0.0041 (2) | 0.0721 (7) | |
H3A | 0.2326 | 0.6615 | 0.0064 | 0.087* | |
C4 | 0.1531 (2) | 0.53006 (17) | 0.0543 (2) | 0.0653 (6) | |
H4A | 0.0891 | 0.5610 | 0.0915 | 0.078* | |
C5 | 0.16142 (18) | 0.42387 (16) | 0.04968 (17) | 0.0546 (5) | |
H5A | 0.1035 | 0.3827 | 0.0837 | 0.066* | |
C6 | 0.25650 (16) | 0.38005 (14) | −0.00589 (15) | 0.0460 (4) | |
C7 | 0.21875 (16) | 0.10653 (14) | −0.03158 (15) | 0.0437 (4) | |
H7A | 0.1815 | 0.0444 | −0.0540 | 0.052* | |
C8 | 0.18333 (15) | 0.20293 (15) | −0.06634 (15) | 0.0433 (4) | |
C9 | 0.08425 (15) | 0.23722 (14) | −0.14967 (15) | 0.0441 (4) | |
C10 | −0.03190 (17) | 0.19422 (15) | −0.15016 (17) | 0.0523 (5) | |
H10A | −0.0474 | 0.1428 | −0.0975 | 0.063* | |
C11 | −0.12620 (17) | 0.22564 (16) | −0.22714 (17) | 0.0543 (5) | |
H11A | −0.2041 | 0.1950 | −0.2266 | 0.065* | |
C12 | −0.10491 (16) | 0.30191 (14) | −0.30416 (15) | 0.0460 (4) | |
C13 | 0.01140 (17) | 0.34379 (16) | −0.30736 (16) | 0.0516 (5) | |
H13A | 0.0269 | 0.3941 | −0.3614 | 0.062* | |
C14 | 0.10531 (17) | 0.31154 (16) | −0.23075 (16) | 0.0507 (5) | |
H14A | 0.1841 | 0.3402 | −0.2337 | 0.061* | |
C15 | 0.32262 (15) | 0.11962 (14) | 0.04482 (14) | 0.0407 (4) | |
C16 | 0.40064 (15) | 0.04285 (14) | 0.10482 (14) | 0.0404 (4) | |
C17 | 0.36890 (17) | −0.06076 (15) | 0.10014 (15) | 0.0476 (4) | |
H17A | 0.2955 | −0.0804 | 0.0603 | 0.057* | |
C18 | 0.44262 (18) | −0.13518 (16) | 0.15259 (17) | 0.0554 (5) | |
H18A | 0.4201 | −0.2044 | 0.1471 | 0.066* | |
C19 | 0.55033 (18) | −0.10638 (17) | 0.21343 (16) | 0.0546 (5) | |
H19A | 0.6000 | −0.1563 | 0.2503 | 0.066* | |
C20 | 0.58441 (18) | −0.00551 (16) | 0.21988 (16) | 0.0525 (5) | |
H20A | 0.6572 | 0.0133 | 0.2613 | 0.063* | |
C21 | 0.51143 (16) | 0.06923 (14) | 0.16520 (15) | 0.0447 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0470 (8) | 0.0663 (9) | 0.0638 (8) | 0.0073 (7) | −0.0160 (6) | 0.0117 (7) |
O2 | 0.0474 (8) | 0.0503 (8) | 0.0796 (10) | 0.0043 (6) | −0.0253 (7) | −0.0134 (7) |
N1 | 0.0380 (8) | 0.0451 (9) | 0.0548 (9) | 0.0054 (7) | −0.0141 (7) | −0.0037 (7) |
N2 | 0.0375 (8) | 0.0480 (9) | 0.0514 (8) | 0.0067 (7) | −0.0119 (7) | −0.0054 (7) |
C1 | 0.0587 (13) | 0.0636 (14) | 0.0668 (13) | −0.0021 (11) | 0.0084 (10) | 0.0014 (11) |
C2 | 0.0867 (18) | 0.0632 (15) | 0.0824 (16) | −0.0137 (14) | 0.0036 (14) | 0.0141 (13) |
C3 | 0.0878 (18) | 0.0479 (12) | 0.0775 (15) | 0.0045 (12) | −0.0202 (14) | 0.0046 (11) |
C4 | 0.0574 (13) | 0.0601 (13) | 0.0764 (14) | 0.0163 (11) | −0.0138 (11) | −0.0140 (11) |
C5 | 0.0446 (10) | 0.0554 (12) | 0.0631 (12) | 0.0036 (9) | −0.0028 (9) | −0.0045 (10) |
C6 | 0.0423 (10) | 0.0457 (10) | 0.0483 (10) | 0.0043 (8) | −0.0104 (8) | −0.0023 (8) |
C7 | 0.0368 (9) | 0.0468 (10) | 0.0467 (9) | −0.0006 (8) | −0.0051 (7) | −0.0039 (8) |
C8 | 0.0324 (8) | 0.0524 (10) | 0.0443 (9) | 0.0035 (8) | −0.0032 (7) | −0.0031 (8) |
C9 | 0.0348 (9) | 0.0504 (10) | 0.0460 (9) | 0.0036 (8) | −0.0063 (7) | −0.0021 (8) |
C10 | 0.0423 (10) | 0.0558 (11) | 0.0572 (11) | −0.0031 (9) | −0.0089 (8) | 0.0118 (9) |
C11 | 0.0363 (9) | 0.0598 (12) | 0.0651 (12) | −0.0072 (9) | −0.0108 (9) | 0.0073 (10) |
C12 | 0.0400 (9) | 0.0490 (10) | 0.0475 (10) | 0.0079 (8) | −0.0103 (8) | −0.0008 (8) |
C13 | 0.0477 (11) | 0.0601 (12) | 0.0465 (10) | −0.0009 (9) | −0.0014 (8) | 0.0095 (9) |
C14 | 0.0359 (9) | 0.0654 (12) | 0.0500 (10) | −0.0050 (9) | −0.0021 (8) | 0.0021 (9) |
C15 | 0.0351 (9) | 0.0465 (10) | 0.0400 (8) | 0.0025 (8) | −0.0022 (7) | −0.0052 (8) |
C16 | 0.0344 (8) | 0.0487 (10) | 0.0375 (8) | 0.0031 (8) | −0.0034 (7) | −0.0033 (7) |
C17 | 0.0415 (10) | 0.0524 (11) | 0.0478 (10) | −0.0047 (8) | −0.0051 (8) | 0.0032 (8) |
C18 | 0.0518 (11) | 0.0526 (12) | 0.0612 (11) | 0.0003 (9) | −0.0005 (9) | 0.0094 (9) |
C19 | 0.0480 (11) | 0.0617 (13) | 0.0540 (11) | 0.0108 (10) | 0.0012 (9) | 0.0122 (10) |
C20 | 0.0407 (10) | 0.0663 (13) | 0.0488 (10) | 0.0059 (9) | −0.0097 (8) | −0.0004 (9) |
C21 | 0.0391 (9) | 0.0491 (10) | 0.0449 (9) | 0.0044 (8) | −0.0052 (8) | −0.0084 (8) |
Geometric parameters (Å, º) top
O1—C12 | 1.362 (2) | C8—C9 | 1.471 (2) |
O1—H1B | 0.8200 | C9—C10 | 1.371 (3) |
O2—C21 | 1.367 (2) | C9—C14 | 1.380 (3) |
O2—H2B | 0.8200 | C10—C11 | 1.379 (3) |
N1—N2 | 1.3549 (19) | C10—H10A | 0.9300 |
N1—C8 | 1.360 (2) | C11—C12 | 1.366 (3) |
N1—C6 | 1.428 (2) | C11—H11A | 0.9300 |
N2—C15 | 1.330 (2) | C12—C13 | 1.370 (3) |
C1—C6 | 1.363 (3) | C13—C14 | 1.376 (3) |
C1—C2 | 1.374 (3) | C13—H13A | 0.9300 |
C1—H1A | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.364 (4) | C15—C16 | 1.455 (2) |
C2—H2A | 0.9300 | C16—C17 | 1.385 (3) |
C3—C4 | 1.369 (3) | C16—C21 | 1.394 (2) |
C3—H3A | 0.9300 | C17—C18 | 1.371 (3) |
C4—C5 | 1.379 (3) | C17—H17A | 0.9300 |
C4—H4A | 0.9300 | C18—C19 | 1.377 (3) |
C5—C6 | 1.371 (3) | C18—H18A | 0.9300 |
C5—H5A | 0.9300 | C19—C20 | 1.358 (3) |
C7—C8 | 1.360 (3) | C19—H19A | 0.9300 |
C7—C15 | 1.401 (2) | C20—C21 | 1.380 (3) |
C7—H7A | 0.9300 | C20—H20A | 0.9300 |
| | | |
C12—O1—H1B | 109.5 | C11—C10—H10A | 119.3 |
C21—O2—H2B | 109.5 | C12—C11—C10 | 119.82 (17) |
N2—N1—C8 | 111.18 (15) | C12—C11—H11A | 120.1 |
N2—N1—C6 | 119.34 (14) | C10—C11—H11A | 120.1 |
C8—N1—C6 | 128.64 (14) | O1—C12—C11 | 123.06 (17) |
C15—N2—N1 | 105.81 (13) | O1—C12—C13 | 117.22 (17) |
C6—C1—C2 | 119.5 (2) | C11—C12—C13 | 119.71 (16) |
C6—C1—H1A | 120.3 | C12—C13—C14 | 120.10 (18) |
C2—C1—H1A | 120.3 | C12—C13—H13A | 120.0 |
C3—C2—C1 | 120.0 (2) | C14—C13—H13A | 120.0 |
C3—C2—H2A | 120.0 | C13—C14—C9 | 120.92 (17) |
C1—C2—H2A | 120.0 | C13—C14—H14A | 119.5 |
C2—C3—C4 | 120.4 (2) | C9—C14—H14A | 119.5 |
C2—C3—H3A | 119.8 | N2—C15—C7 | 110.14 (15) |
C4—C3—H3A | 119.8 | N2—C15—C16 | 119.87 (15) |
C3—C4—C5 | 120.0 (2) | C7—C15—C16 | 129.96 (16) |
C3—C4—H4A | 120.0 | C17—C16—C21 | 117.38 (16) |
C5—C4—H4A | 120.0 | C17—C16—C15 | 120.54 (15) |
C6—C5—C4 | 118.9 (2) | C21—C16—C15 | 122.04 (16) |
C6—C5—H5A | 120.5 | C18—C17—C16 | 121.86 (18) |
C4—C5—H5A | 120.5 | C18—C17—H17A | 119.1 |
C1—C6—C5 | 121.20 (19) | C16—C17—H17A | 119.1 |
C1—C6—N1 | 119.94 (18) | C17—C18—C19 | 119.33 (19) |
C5—C6—N1 | 118.86 (18) | C17—C18—H18A | 120.3 |
C8—C7—C15 | 106.22 (15) | C19—C18—H18A | 120.3 |
C8—C7—H7A | 126.9 | C20—C19—C18 | 120.44 (18) |
C15—C7—H7A | 126.9 | C20—C19—H19A | 119.8 |
N1—C8—C7 | 106.65 (14) | C18—C19—H19A | 119.8 |
N1—C8—C9 | 122.37 (17) | C19—C20—C21 | 120.24 (18) |
C7—C8—C9 | 130.90 (17) | C19—C20—H20A | 119.9 |
C10—C9—C14 | 117.98 (16) | C21—C20—H20A | 119.9 |
C10—C9—C8 | 120.49 (17) | O2—C21—C20 | 117.24 (16) |
C14—C9—C8 | 121.51 (16) | O2—C21—C16 | 122.02 (16) |
C9—C10—C11 | 121.40 (18) | C20—C21—C16 | 120.73 (18) |
C9—C10—H10A | 119.3 | | |
| | | |
C8—N1—N2—C15 | 0.7 (2) | C10—C11—C12—O1 | −178.41 (18) |
C6—N1—N2—C15 | 171.10 (16) | C10—C11—C12—C13 | 2.6 (3) |
C6—C1—C2—C3 | −0.4 (4) | O1—C12—C13—C14 | 178.78 (17) |
C1—C2—C3—C4 | 1.2 (4) | C11—C12—C13—C14 | −2.2 (3) |
C2—C3—C4—C5 | −0.9 (3) | C12—C13—C14—C9 | −0.2 (3) |
C3—C4—C5—C6 | −0.1 (3) | C10—C9—C14—C13 | 2.0 (3) |
C2—C1—C6—C5 | −0.7 (3) | C8—C9—C14—C13 | −179.23 (17) |
C2—C1—C6—N1 | 179.36 (19) | N1—N2—C15—C7 | −0.6 (2) |
C4—C5—C6—C1 | 0.9 (3) | N1—N2—C15—C16 | 177.64 (15) |
C4—C5—C6—N1 | −179.09 (17) | C8—C7—C15—N2 | 0.4 (2) |
N2—N1—C6—C1 | 76.2 (2) | C8—C7—C15—C16 | −177.66 (17) |
C8—N1—C6—C1 | −115.2 (2) | N2—C15—C16—C17 | 175.03 (17) |
N2—N1—C6—C5 | −103.7 (2) | C7—C15—C16—C17 | −7.1 (3) |
C8—N1—C6—C5 | 64.8 (3) | N2—C15—C16—C21 | −7.4 (3) |
N2—N1—C8—C7 | −0.4 (2) | C7—C15—C16—C21 | 170.51 (18) |
C6—N1—C8—C7 | −169.74 (17) | C21—C16—C17—C18 | 0.1 (3) |
N2—N1—C8—C9 | −177.64 (16) | C15—C16—C17—C18 | 177.79 (17) |
C6—N1—C8—C9 | 13.1 (3) | C16—C17—C18—C19 | 1.1 (3) |
C15—C7—C8—N1 | 0.0 (2) | C17—C18—C19—C20 | −1.1 (3) |
C15—C7—C8—C9 | 176.91 (18) | C18—C19—C20—C21 | −0.1 (3) |
N1—C8—C9—C10 | −138.9 (2) | C19—C20—C21—O2 | −177.28 (18) |
C7—C8—C9—C10 | 44.6 (3) | C19—C20—C21—C16 | 1.4 (3) |
N1—C8—C9—C14 | 42.4 (3) | C17—C16—C21—O2 | 177.27 (17) |
C7—C8—C9—C14 | −134.1 (2) | C15—C16—C21—O2 | −0.4 (3) |
C14—C9—C10—C11 | −1.6 (3) | C17—C16—C21—C20 | −1.4 (3) |
C8—C9—C10—C11 | 179.66 (18) | C15—C16—C21—C20 | −179.04 (17) |
C9—C10—C11—C12 | −0.7 (3) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O2i | 0.82 | 2.05 | 2.824 (2) | 158 |
O2—H2B···N2 | 0.82 | 1.87 | 2.595 (2) | 147 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
Experimental details
Crystal data |
Chemical formula | C21H16N2O2 |
Mr | 328.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 298 |
a, b, c (Å) | 10.793 (3), 12.948 (3), 11.705 (3) |
β (°) | 93.508 (14) |
V (Å3) | 1632.7 (7) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.44 × 0.40 × 0.26 |
|
Data collection |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5767, 3720, 2353 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.650 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.128, 1.03 |
No. of reflections | 3720 |
No. of parameters | 227 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.15, −0.16 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···O2i | 0.820 | 2.047 | 2.824 (2) | 157.87 |
O2—H2B···N2 | 0.820 | 1.870 | 2.595 (2) | 146.72 |
Symmetry code: (i) x−1, −y+1/2, z−1/2. |
Pyrazoles are important because of their potential for biological activity (Beeam et al., 1984). Both traditional and new scientific methods have been used used to prepare new materials for medicine (Elguero et al., 1983) and agriculture (Trofinenko, 1972). Neutral and anionic pyrazoles are excellent ligands and their co-ordination chemistry has been extensively studied (Bonati, 1980). In the molecular structure of the title compound (III) (Fig. 1 and Fig. 3) there is an intramolecular hydrogen bond between the OH group of one phenolic group and the N atom of the pyrazole group (see Table 1 for hydrogen bond details). One of the phenyl groups is approximately coplanar with the pyrazole groups (dihedral angle = 7.5 (3)°), possibly due to the intramolecular hydrogen bond formation. The other two phenyl groups are rotated by 66.4 (12)°. In the crystal structure an intermolecular hydrogen bond between non equivalent hydroxy groups of symmetry related molecules, forms extended chains along [201] (Fig. 2).