2,2′-(1-Phenyl-1H-pyrazole-3,5-di­yl)diphenol

Ikram, S.; Zia ul Haq, M.; Badshah, A.; Hasan, A.; Bolte, M.

doi:10.1107/S1600536809001226

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o364

doi:10.1107/S1600536809001226

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2,2′-(1-Phenyl-1H-pyrazole-3,5-diyl)diphenol

Sumeera Ikram,^a Muhammad Zia ul Haq,^a Amir Badshah,^a Aurangzeb Hasan ^a ^* and Michael Bolte ^b

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bInstitut für Anorganische Chemie, J. W. Goethe-Universität, Max-von-Laue-Strasse 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: h.aurangzeb@yahoo.com

(Received 9 January 2009; accepted 10 January 2009; online 23 January 2009)

The title compound, C₂₁H₁₆N₂O₂, was derived from 1-(2-hydroxyphenyl)-3-(-methoxyphenyl)propane-1,3-dione. The molecular structure of the title compound is stabilized by an intramolecular O—H⋯N hydrogen bond. The dihedral angle between the hydroxyphenyl ring involved in this intramolecular hydrogen bond and the pyrazole ring is significantly smaller [10.07 (6)°] than the dihedral angle between the pyrazole and the other hydroxyphenyl ring [36.64 (5)°]. The benzene ring makes a dihedral angle of 54.95 (3)° with the pyrazole ring. The crystal packing is stabilized by O—H⋯O and O—H⋯N hydrogen bonds.

Related literature

For the biological activity of pyrazoles, see: Beeam et al. (1984 ). For the preparation of new materials for medicine, see: Elguero (1983 ). For the coordination chemistry of pyrazoles, see: Bonati (1980 ). For their use as analytical reagents, see: Freyer & Radeglia (1981 ). For the synthesis of 1-(2′-hydroxyphenyl)-3-(2′′-methoxyphenyl)propane-1,3-dione, see: Ahmad et al. (1997 ).

Experimental

Crystal data

C₂₁H₁₆N₂O₂
M_r = 328.36
Monoclinic, P 2₁ /c
a = 9.7034 (8) Å
b = 11.7407 (9) Å
c = 14.9486 (14) Å
β = 104.294 (7)°
V = 1650.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 173 (2) K
0.48 × 0.46 × 0.46 mm

Data collection

Stoe IPDSII two-circle diffractometer
Absorption correction: none
12165 measured reflections
3799 independent reflections
3235 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.03
3799 reflections
235 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.94 (2)	1.81 (2)	2.7524 (12)	176.6 (19)
O1—H1⋯N2	0.947 (19)	1.718 (19)	2.5863 (12)	150.9 (17)
Symmetry code: (i) x+1, y, z.

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: PLATON (Spek, 2003 ) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809001226/bx2193sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001226/bx2193Isup2.hkl

checkCIF report

Comment top

Pyrazoles are important because of their potential for biological activity. They have antipuretic, anti-inflammatory and antirheumatic effects (Beeam et al., 1984). Both traditional and new scientific methods have been used to prepare new materials for medicine (Elguero et al., 1983) and agriculture (Trofimenko, 1972). Neutral and anionic pyrazoles are excellent ligands and their co-ordination chemistry has been extensively studied (Bonati, 1980). Pyrazoles are also used as analytical reagents (Freyer et al., 1981) The molecular structure of the title compound is stabilized by an intramolecular O-H···N hydrogen bond. The dihedral angle between the hydroxyphenyl ring involved in this intramolecular hydrogen bond is significantly smaller [10.07 (6)°] than the dihedral angle between the pyrazole and the other hydroxyphenyl ring [36.64 (5)°]. The phenyl ring makes a makes dihedral angle of 54.95 (3)° with the pyrazol ring. The crystal packing is stabilized by O-H···O hydrogen bonds.

Related literature top

For the biological activity of pyrazoles, see: Beeam et al. (1984). For the preparation of prepare new materials for medicine, see: Elguero (1983); and agriculture, see: Trofimenko (1972). For the corrdination chemistry of pyrazoles, see: Bonati (1980). For their use as analytical reagents, see: Freyer & Radeglia (1981). For the synthesis of 1-(2'-hydroxyphenyl)-3-(2"-methoxyphenyl) propane-1,3-dione, see: Ahmad et al. (1997).

Experimental top

1-(2'-hydroxyphenyl)-3-(2"-methoxyphenyl) propane-1,3-dione (I) was prepared by a modified Baker Venkataram rearrangement as reported earlier (Ahmad et al. 1997). 1-Phenyl-3,5-bis(2'-hydroxy phenyl)phyrazole(III) was synthesized by demethylation of 2-(5-(2-methoxyphenyl)-1-phenyl-1H-pyrazol-3-yl)phenol(II), which was prepared by refluxing 1-(2'-hydroxyphenyl)-3-(2"-methoxyphenyl) propane-1,3-dione (2.7 g, 10 mmol) with phenyl hydrazine (1.08 g,0.99 ml, 10 mmol) in 100 ml absolute ethanol for seven hours as shown in Fig. 3. The product was recrystallized using absolute ethanol. (yield: 90%, m.p: 473k)

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: 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: PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of(I) showing the formation of a one-dimensional chain along [100] direction and the hydrogen-bonding and O-H···N intramolecular contact.
	Fig. 3. Preparation of the title compound.

2,2'-(1-Phenyl-1H-pyrazole-3,5-diyl)diphenol top

Crystal data top

C₂₁H₁₆N₂O₂	F(000) = 688
M_r = 328.36	D_x = 1.322 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 473 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.7034 (8) Å	Cell parameters from 10768 reflections
b = 11.7407 (9) Å	θ = 3.6–27.6°
c = 14.9486 (14) Å	µ = 0.09 mm⁻¹
β = 104.294 (7)°	T = 173 K
V = 1650.3 (2) Å³	Block, colourless
Z = 4	0.48 × 0.46 × 0.46 mm

Data collection top

Stoe IPDSII two-circle diffractometer	3235 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
Graphite monochromator	θ_max = 27.6°, θ_min = 3.6°
ω scans	h = −12→12
12165 measured reflections	k = −13→15
3799 independent reflections	l = −18→19

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)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0529P)² + 0.3119P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3799 reflections	Δρ_max = 0.24 e Å⁻³
235 parameters	Δρ_min = −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: 0.030 (2)

Crystal data top

C₂₁H₁₆N₂O₂	V = 1650.3 (2) Å³
M_r = 328.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.7034 (8) Å	µ = 0.09 mm⁻¹
b = 11.7407 (9) Å	T = 173 K
c = 14.9486 (14) Å	0.48 × 0.46 × 0.46 mm
β = 104.294 (7)°

Data collection top

Stoe IPDSII two-circle diffractometer	3235 reflections with I > 2σ(I)
12165 measured reflections	R_int = 0.034
3799 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.24 e Å⁻³
3799 reflections	Δρ_min = −0.15 e Å⁻³
235 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.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.72854 (9)	0.56525 (9)	0.70176 (6)	0.0273 (2)
N2	0.60684 (9)	0.61144 (9)	0.64778 (6)	0.0277 (2)
O1	0.34395 (9)	0.66647 (10)	0.57881 (6)	0.0434 (3)
H1	0.428 (2)	0.6418 (18)	0.6211 (13)	0.068 (6)*
O2	1.07930 (9)	0.61561 (9)	0.60415 (7)	0.0416 (2)
H2	1.170 (2)	0.6300 (17)	0.5950 (13)	0.073 (6)*
C3	0.63161 (11)	0.62529 (9)	0.56362 (7)	0.0250 (2)
C4	0.76965 (11)	0.58763 (10)	0.56388 (7)	0.0267 (2)
H4	0.8130	0.5885	0.5134	0.032*
C5	0.82919 (11)	0.54909 (9)	0.65248 (7)	0.0260 (2)
C11	0.73784 (12)	0.55181 (10)	0.79885 (7)	0.0293 (2)
C12	0.84714 (13)	0.60411 (11)	0.86344 (8)	0.0354 (3)
H12	0.9170	0.6479	0.8442	0.042*
C13	0.85265 (15)	0.59125 (13)	0.95705 (9)	0.0447 (3)
H13	0.9274	0.6257	1.0021	0.054*
C14	0.74906 (17)	0.52810 (14)	0.98457 (9)	0.0479 (4)
H14	0.7532	0.5197	1.0484	0.057*
C15	0.63982 (16)	0.47744 (13)	0.91924 (9)	0.0437 (3)
H15	0.5689	0.4349	0.9384	0.052*
C16	0.63368 (13)	0.48862 (11)	0.82558 (8)	0.0349 (3)
H16	0.5593	0.4535	0.7806	0.042*
C31	0.51991 (11)	0.67507 (9)	0.48859 (7)	0.0260 (2)
C32	0.38098 (12)	0.69291 (11)	0.49811 (8)	0.0308 (2)
C33	0.27648 (13)	0.73925 (12)	0.42651 (9)	0.0399 (3)
H33	0.1826	0.7492	0.4336	0.048*
C34	0.30899 (14)	0.77093 (12)	0.34478 (9)	0.0409 (3)
H34	0.2378	0.8035	0.2962	0.049*
C35	0.44618 (15)	0.75502 (12)	0.33381 (8)	0.0395 (3)
H35	0.4687	0.7765	0.2778	0.047*
C36	0.54978 (13)	0.70771 (11)	0.40505 (8)	0.0329 (3)
H36	0.6431	0.6972	0.3971	0.040*
C51	0.96705 (11)	0.49298 (10)	0.69189 (7)	0.0270 (2)
C52	1.08989 (12)	0.52664 (10)	0.66442 (8)	0.0304 (2)
C53	1.21876 (13)	0.46994 (11)	0.69982 (9)	0.0368 (3)
H53	1.3013	0.4927	0.6811	0.044*
C54	1.22731 (13)	0.38090 (11)	0.76202 (9)	0.0385 (3)
H54	1.3155	0.3433	0.7856	0.046*
C55	1.10706 (14)	0.34660 (11)	0.78991 (8)	0.0364 (3)
H55	1.1127	0.2858	0.8326	0.044*
C56	0.97871 (13)	0.40228 (10)	0.75474 (8)	0.0317 (3)
H56	0.8967	0.3784	0.7737	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0242 (4)	0.0347 (5)	0.0222 (4)	0.0020 (4)	0.0044 (3)	0.0012 (4)
N2	0.0238 (4)	0.0358 (5)	0.0225 (4)	0.0015 (4)	0.0037 (3)	0.0012 (4)
O1	0.0252 (4)	0.0723 (7)	0.0332 (5)	0.0042 (4)	0.0082 (4)	0.0121 (4)
O2	0.0270 (4)	0.0485 (6)	0.0511 (5)	0.0055 (4)	0.0130 (4)	0.0173 (4)
C3	0.0258 (5)	0.0271 (5)	0.0216 (5)	−0.0035 (4)	0.0047 (4)	−0.0019 (4)
C4	0.0270 (5)	0.0299 (6)	0.0235 (5)	−0.0019 (4)	0.0070 (4)	−0.0021 (4)
C5	0.0248 (5)	0.0268 (5)	0.0266 (5)	−0.0013 (4)	0.0066 (4)	−0.0027 (4)
C11	0.0312 (5)	0.0343 (6)	0.0222 (5)	0.0058 (5)	0.0065 (4)	0.0023 (4)
C12	0.0339 (6)	0.0421 (7)	0.0283 (6)	0.0023 (5)	0.0041 (5)	−0.0004 (5)
C13	0.0484 (7)	0.0549 (9)	0.0262 (6)	0.0066 (6)	0.0002 (5)	−0.0023 (6)
C14	0.0656 (9)	0.0546 (9)	0.0243 (6)	0.0107 (7)	0.0127 (6)	0.0059 (6)
C15	0.0552 (8)	0.0448 (8)	0.0359 (7)	0.0039 (6)	0.0201 (6)	0.0090 (6)
C16	0.0371 (6)	0.0373 (6)	0.0313 (6)	0.0017 (5)	0.0102 (5)	0.0028 (5)
C31	0.0272 (5)	0.0260 (5)	0.0228 (5)	−0.0037 (4)	0.0026 (4)	−0.0019 (4)
C32	0.0279 (5)	0.0354 (6)	0.0276 (5)	−0.0033 (4)	0.0038 (4)	0.0011 (5)
C33	0.0293 (6)	0.0458 (7)	0.0394 (7)	0.0004 (5)	−0.0013 (5)	0.0041 (6)
C34	0.0420 (7)	0.0379 (7)	0.0337 (6)	−0.0039 (5)	−0.0079 (5)	0.0066 (5)
C35	0.0506 (7)	0.0385 (7)	0.0261 (5)	−0.0070 (6)	0.0033 (5)	0.0049 (5)
C36	0.0367 (6)	0.0355 (6)	0.0263 (5)	−0.0038 (5)	0.0071 (4)	0.0005 (5)
C51	0.0267 (5)	0.0276 (5)	0.0256 (5)	0.0017 (4)	0.0040 (4)	−0.0026 (4)
C52	0.0285 (5)	0.0316 (6)	0.0307 (5)	0.0026 (4)	0.0066 (4)	0.0000 (5)
C53	0.0280 (6)	0.0393 (7)	0.0422 (7)	0.0052 (5)	0.0072 (5)	−0.0010 (5)
C54	0.0347 (6)	0.0360 (7)	0.0411 (7)	0.0106 (5)	0.0024 (5)	−0.0016 (5)
C55	0.0443 (7)	0.0297 (6)	0.0326 (6)	0.0071 (5)	0.0048 (5)	0.0013 (5)
C56	0.0357 (6)	0.0297 (6)	0.0296 (5)	0.0003 (5)	0.0078 (5)	−0.0020 (5)

Geometric parameters (Å, º) top

N1—N2	1.3672 (13)	C15—H15	0.9500
N1—C5	1.3740 (13)	C16—H16	0.9500
N1—C11	1.4403 (13)	C31—C36	1.4033 (15)
N2—C3	1.3477 (13)	C31—C32	1.4057 (15)
O1—C32	1.3765 (14)	C32—C33	1.3907 (17)
O1—H1	0.947 (19)	C33—C34	1.3859 (18)
O2—C52	1.3666 (15)	C33—H33	0.9500
O2—H2	0.94 (2)	C34—C35	1.3935 (19)
C3—C4	1.4097 (15)	C34—H34	0.9500
C3—C31	1.4744 (15)	C35—C36	1.3873 (17)
C4—C5	1.3838 (15)	C35—H35	0.9500
C4—H4	0.9500	C36—H36	0.9500
C5—C51	1.4769 (15)	C51—C56	1.4060 (16)
C11—C12	1.3887 (17)	C51—C52	1.4098 (15)
C11—C16	1.3896 (16)	C52—C53	1.4000 (16)
C12—C13	1.3953 (17)	C53—C54	1.3878 (19)
C12—H12	0.9500	C53—H53	0.9500
C13—C14	1.391 (2)	C54—C55	1.3921 (19)
C13—H13	0.9500	C54—H54	0.9500
C14—C15	1.386 (2)	C55—C56	1.3898 (17)
C14—H14	0.9500	C55—H55	0.9500
C15—C16	1.3928 (17)	C56—H56	0.9500

N2—N1—C5	111.28 (8)	C32—C31—C3	121.69 (9)
N2—N1—C11	117.92 (8)	O1—C32—C33	117.66 (11)
C5—N1—C11	130.48 (9)	O1—C32—C31	121.29 (10)
C3—N2—N1	105.77 (8)	C33—C32—C31	121.04 (11)
C32—O1—H1	106.6 (11)	C34—C33—C32	120.13 (12)
C52—O2—H2	108.2 (12)	C34—C33—H33	119.9
N2—C3—C4	110.36 (9)	C32—C33—H33	119.9
N2—C3—C31	119.40 (9)	C33—C34—C35	119.98 (11)
C4—C3—C31	130.24 (9)	C33—C34—H34	120.0
C5—C4—C3	106.08 (9)	C35—C34—H34	120.0
C5—C4—H4	127.0	C36—C35—C34	119.72 (11)
C3—C4—H4	127.0	C36—C35—H35	120.1
N1—C5—C4	106.50 (9)	C34—C35—H35	120.1
N1—C5—C51	122.78 (9)	C35—C36—C31	121.51 (11)
C4—C5—C51	130.59 (9)	C35—C36—H36	119.2
C12—C11—C16	121.40 (11)	C31—C36—H36	119.2
C12—C11—N1	119.95 (10)	C56—C51—C52	118.20 (10)
C16—C11—N1	118.63 (10)	C56—C51—C5	121.32 (10)
C11—C12—C13	118.88 (12)	C52—C51—C5	120.43 (10)
C11—C12—H12	120.6	O2—C52—C53	121.84 (10)
C13—C12—H12	120.6	O2—C52—C51	118.35 (10)
C14—C13—C12	120.19 (13)	C53—C52—C51	119.81 (11)
C14—C13—H13	119.9	C54—C53—C52	120.77 (11)
C12—C13—H13	119.9	C54—C53—H53	119.6
C15—C14—C13	120.23 (12)	C52—C53—H53	119.6
C15—C14—H14	119.9	C53—C54—C55	120.18 (11)
C13—C14—H14	119.9	C53—C54—H54	119.9
C14—C15—C16	120.23 (13)	C55—C54—H54	119.9
C14—C15—H15	119.9	C56—C55—C54	119.32 (12)
C16—C15—H15	119.9	C56—C55—H55	120.3
C11—C16—C15	119.06 (12)	C54—C55—H55	120.3
C11—C16—H16	120.5	C55—C56—C51	121.72 (11)
C15—C16—H16	120.5	C55—C56—H56	119.1
C36—C31—C32	117.60 (10)	C51—C56—H56	119.1
C36—C31—C3	120.71 (10)

C5—N1—N2—C3	−0.45 (12)	C4—C3—C31—C32	170.94 (11)
C11—N1—N2—C3	173.77 (10)	C36—C31—C32—O1	−178.03 (11)
N1—N2—C3—C4	0.08 (12)	C3—C31—C32—O1	1.20 (17)
N1—N2—C3—C31	−179.44 (9)	C36—C31—C32—C33	1.20 (18)
N2—C3—C4—C5	0.30 (13)	C3—C31—C32—C33	−179.57 (12)
C31—C3—C4—C5	179.76 (11)	O1—C32—C33—C34	177.90 (12)
N2—N1—C5—C4	0.63 (13)	C31—C32—C33—C34	−1.4 (2)
C11—N1—C5—C4	−172.65 (11)	C32—C33—C34—C35	0.8 (2)
N2—N1—C5—C51	−175.58 (10)	C33—C34—C35—C36	−0.2 (2)
C11—N1—C5—C51	11.14 (19)	C34—C35—C36—C31	0.0 (2)
C3—C4—C5—N1	−0.55 (12)	C32—C31—C36—C35	−0.55 (18)
C3—C4—C5—C51	175.26 (11)	C3—C31—C36—C35	−179.78 (11)
N2—N1—C11—C12	−121.61 (12)	N1—C5—C51—C56	35.52 (16)
C5—N1—C11—C12	51.30 (18)	C4—C5—C51—C56	−139.69 (13)
N2—N1—C11—C16	56.64 (15)	N1—C5—C51—C52	−146.91 (11)
C5—N1—C11—C16	−130.45 (13)	C4—C5—C51—C52	37.88 (18)
C16—C11—C12—C13	0.84 (19)	C56—C51—C52—O2	−179.27 (11)
N1—C11—C12—C13	179.04 (11)	C5—C51—C52—O2	3.09 (16)
C11—C12—C13—C14	−0.8 (2)	C56—C51—C52—C53	−0.05 (17)
C12—C13—C14—C15	0.1 (2)	C5—C51—C52—C53	−177.69 (10)
C13—C14—C15—C16	0.5 (2)	O2—C52—C53—C54	179.03 (12)
C12—C11—C16—C15	−0.23 (18)	C51—C52—C53—C54	−0.17 (18)
N1—C11—C16—C15	−178.46 (11)	C52—C53—C54—C55	0.14 (19)
C14—C15—C16—C11	−0.5 (2)	C53—C54—C55—C56	0.10 (19)
N2—C3—C31—C36	169.56 (11)	C54—C55—C56—C51	−0.32 (18)
C4—C3—C31—C36	−9.85 (18)	C52—C51—C56—C55	0.29 (17)
N2—C3—C31—C32	−9.64 (16)	C5—C51—C56—C55	177.91 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.94 (2)	1.81 (2)	2.7524 (12)	176.6 (19)
O1—H1···N2	0.947 (19)	1.718 (19)	2.5863 (12)	150.9 (17)

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₆N₂O₂
M_r	328.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.7034 (8), 11.7407 (9), 14.9486 (14)
β (°)	104.294 (7)
V (Å³)	1650.3 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.46 × 0.46

Data collection
Diffractometer	Stoe IPDSII two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12165, 3799, 3235
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.03
No. of reflections	3799
No. of parameters	235
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.15

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2003) and XP in SHELXTL-Plus (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.94 (2)	1.81 (2)	2.7524 (12)	176.6 (19)
O1—H1···N2	0.947 (19)	1.718 (19)	2.5863 (12)	150.9 (17)

Symmetry code: (i) x+1, y, z.

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for a grant.

References

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