2-[3-(4-Methoxyphen­yl)-1-phenyl-1H-pyrazol-5-yl]phenol

Kausar, R.; Badshah, A.; Zia ul Haq, M.; Hasan, A.; Bolte, M.

doi:10.1107/S1600536809004012

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o589

doi:10.1107/S1600536809004012

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2-[3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl]phenol

Rukhsana Kausar,^a Amir Badshah,^b Muhammad Zia ul Haq,^b Aurangzeb Hasan ^b ^* and Michael Bolte ^c

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

(Received 28 January 2009; accepted 3 February 2009; online 25 February 2009)

The title compound, C₂₂H₁₈N₂O₂, was derived from 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)propane-1,3-dione. The central pyrazole ring forms dihedral angles of 16.83 (5), 48.97 (4) and 51.68 (4)°, respectively, with the methoxyphenyl, phenyl and hydroxyphenyl rings. The crystal packing is stabilized by O—H⋯N hydrogen bonding.

Related literature

For general synthesis, see: Ahmad et al. (1997 ). For synthetic applications, see: Beeam et al. (1984 ); Bonati (1980 ); Elguero (1983 ); Freyer & Radeglia (1981 ); Trofinenko (1972 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₂
M_r = 342.38
Monoclinic, P 2₁ /c
a = 9.5880 (5) Å
b = 13.7397 (8) Å
c = 14.2771 (7) Å
β = 109.340 (4)°
V = 1774.68 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 173 (2) K
0.33 × 0.31 × 0.26 mm

Data collection

Stoe IPDS-II two-circle diffractometer
Absorption correction: none
24784 measured reflections
4085 independent reflections
3676 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.096
S = 1.02
4085 reflections
241 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2ⁱ	0.91 (2)	1.88 (2)	2.7894 (11)	175.0 (17)
Symmetry code: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809004012/pk2149sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809004012/pk2149Isup2.hkl

checkCIF report

Comment top

Pyrazoles are important because of their potential for biological activity. They have antipruritic, 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 (Trofinenko, 1972). Neutral and anionic pyrazoles are excellent ligands and their coordination chemistry has been extensively studied (Bonati, 1980). Pyrazoles are also used as analytical reagents (Freyer & Radeglia, 1981). In the molecular structure of the title compound, C₂₂H₁₈N₂O₂, (Scheme 1, Fig. 1) the central pyrazole ring forms dihedral angles of 16.83 (5)°, 48.97 (4)° and 51.68 (4)° with the methoxyphenyl, phenyl and hydroxyphenyl rings, respectively. The crystal packing is stabilized by an O-H···N hydrogen bond (Table 1).

Related literature top

For general synthesis, see: Ahmad et al. (1997). For synthetic applications, see: Beeam et al. (1984); Bonati (1980); Elguero (1983); Freyer & Radeglia (1981); Trofinenko (1972).

Experimental top

1-(2'-Hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione was prepared by a modified Baker Venkataram rearrangement as reported earlier (Ahmad et al. 1997). 2-(3-(4-methxyphenyl)-1-Phenyl-1H-pyrazol-5-yl)phenol was prepared by refluxing 1-(2'-hydroxyphenyl)-3-(4"-methoxyphenyl) propane-1,3-dione (2.7 g, 10 mmol) with phenyl hydrazine (1.08 g,0.99 ml, 10 mmol) in a mixture of 50 ml absolute ethanol and 15 ml glacial acetic acid for seven hours as shown in scheme 2.The oily mixture obtained was purified by a dry silica gel column. The product was recrystallized using absolute ethanol. (Yield: 45%, m.p: 449k)

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: 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 with displacement ellipsoids at the 50% probability level.
	Fig. 2. Packing diagram of the title compound.
	Fig. 3. The formation of the title compound.

2-[3-(4-Methoxyphenyl)-1-phenyl-1H-pyrazol-5-yl]phenol top

Crystal data top

C₂₂H₁₈N₂O₂	F(000) = 720
M_r = 342.38	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 449 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 9.5880 (5) Å	Cell parameters from 22780 reflections
b = 13.7397 (8) Å	θ = 3.8–27.6°
c = 14.2771 (7) Å	µ = 0.08 mm⁻¹
β = 109.340 (4)°	T = 173 K
V = 1774.68 (16) Å³	Block, colourless
Z = 4	0.33 × 0.31 × 0.26 mm

Data collection top

Stoe IPDS-II two-circle diffractometer	3676 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 27.7°, θ_min = 3.7°
ω scans	h = −12→12
24784 measured reflections	k = −17→17
4085 independent reflections	l = −18→18

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0463P)² + 0.5301P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4085 reflections	Δρ_max = 0.28 e Å⁻³
241 parameters	Δρ_min = −0.21 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

C₂₂H₁₈N₂O₂	V = 1774.68 (16) Å³
M_r = 342.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5880 (5) Å	µ = 0.08 mm⁻¹
b = 13.7397 (8) Å	T = 173 K
c = 14.2771 (7) Å	0.33 × 0.31 × 0.26 mm
β = 109.340 (4)°

Data collection top

Stoe IPDS-II two-circle diffractometer	3676 reflections with I > 2σ(I)
24784 measured reflections	R_int = 0.051
4085 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.28 e Å⁻³
4085 reflections	Δρ_min = −0.21 e Å⁻³
241 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
O1	−0.16266 (8)	0.90595 (6)	0.46141 (6)	0.0317 (2)
O2	0.53923 (9)	0.76222 (6)	0.18033 (6)	0.02732 (18)
H2	0.513 (2)	0.7794 (13)	0.1149 (15)	0.058 (5)*
N1	0.54331 (9)	0.65343 (6)	0.43688 (6)	0.02103 (18)
N2	0.44634 (9)	0.69329 (6)	0.47836 (6)	0.02183 (18)
C3	0.33084 (11)	0.72394 (7)	0.40111 (7)	0.0216 (2)
C4	0.35458 (11)	0.70369 (7)	0.31053 (8)	0.0233 (2)
H4	0.2901	0.7185	0.2456	0.028*
C5	0.49012 (11)	0.65812 (7)	0.33524 (7)	0.0209 (2)
C11	0.68123 (11)	0.61521 (7)	0.50071 (7)	0.0208 (2)
C12	0.68218 (12)	0.55147 (8)	0.57656 (8)	0.0256 (2)
H12	0.5924	0.5341	0.5868	0.031*
C13	0.81636 (13)	0.51336 (9)	0.63747 (9)	0.0335 (3)
H13	0.8182	0.4697	0.6895	0.040*
C14	0.94712 (13)	0.53896 (10)	0.62233 (10)	0.0402 (3)
H14	1.0382	0.5123	0.6635	0.048*
C15	0.94514 (13)	0.60346 (11)	0.54719 (11)	0.0408 (3)
H15	1.0351	0.6213	0.5376	0.049*
C16	0.81212 (12)	0.64223 (9)	0.48577 (9)	0.0302 (2)
H16	0.8108	0.6865	0.4344	0.036*
C31	0.20092 (11)	0.77139 (7)	0.41556 (8)	0.0221 (2)
C32	0.06812 (12)	0.77997 (8)	0.33677 (8)	0.0268 (2)
H32	0.0621	0.7544	0.2737	0.032*
C33	−0.05622 (12)	0.82502 (8)	0.34791 (8)	0.0268 (2)
H33	−0.1452	0.8301	0.2931	0.032*
C34	−0.04804 (11)	0.86244 (8)	0.44031 (8)	0.0241 (2)
C35	0.08451 (12)	0.85507 (9)	0.51998 (8)	0.0295 (2)
H35	0.0905	0.8808	0.5829	0.035*
C36	0.20682 (12)	0.81060 (9)	0.50782 (8)	0.0282 (2)
H36	0.2960	0.8065	0.5625	0.034*
C37	−0.29807 (12)	0.92114 (10)	0.38164 (9)	0.0363 (3)
H37A	−0.2786	0.9593	0.3293	0.054*
H37B	−0.3677	0.9565	0.4063	0.054*
H37C	−0.3406	0.8581	0.3547	0.054*
C51	0.56695 (10)	0.61401 (7)	0.27101 (7)	0.0205 (2)
C52	0.58662 (11)	0.66787 (7)	0.19256 (7)	0.0216 (2)
C53	0.65634 (12)	0.62480 (9)	0.13073 (8)	0.0287 (2)
H53	0.6725	0.6618	0.0791	0.034*
C54	0.70182 (12)	0.52839 (9)	0.14464 (8)	0.0306 (2)
H54	0.7480	0.4995	0.1020	0.037*
C55	0.68004 (12)	0.47382 (8)	0.22094 (8)	0.0279 (2)
H55	0.7097	0.4075	0.2297	0.033*
C56	0.61481 (11)	0.51682 (8)	0.28402 (8)	0.0244 (2)
H56	0.6023	0.4799	0.3369	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0251 (4)	0.0429 (5)	0.0281 (4)	0.0094 (3)	0.0101 (3)	−0.0034 (3)
O2	0.0397 (4)	0.0253 (4)	0.0199 (4)	0.0030 (3)	0.0138 (3)	0.0021 (3)
N1	0.0234 (4)	0.0236 (4)	0.0191 (4)	0.0017 (3)	0.0110 (3)	−0.0009 (3)
N2	0.0247 (4)	0.0239 (4)	0.0207 (4)	0.0018 (3)	0.0126 (3)	−0.0017 (3)
C3	0.0256 (5)	0.0209 (5)	0.0209 (5)	0.0004 (4)	0.0111 (4)	0.0002 (4)
C4	0.0274 (5)	0.0248 (5)	0.0199 (5)	0.0028 (4)	0.0110 (4)	0.0016 (4)
C5	0.0262 (5)	0.0203 (4)	0.0190 (5)	−0.0006 (4)	0.0112 (4)	0.0004 (4)
C11	0.0216 (5)	0.0211 (4)	0.0203 (5)	−0.0012 (4)	0.0079 (4)	−0.0038 (4)
C12	0.0268 (5)	0.0274 (5)	0.0228 (5)	−0.0031 (4)	0.0086 (4)	−0.0004 (4)
C13	0.0376 (6)	0.0311 (6)	0.0267 (5)	0.0028 (5)	0.0039 (5)	0.0009 (5)
C14	0.0266 (6)	0.0460 (7)	0.0402 (7)	0.0074 (5)	0.0007 (5)	−0.0048 (6)
C15	0.0217 (5)	0.0527 (8)	0.0487 (7)	−0.0039 (5)	0.0127 (5)	−0.0075 (6)
C16	0.0283 (5)	0.0327 (6)	0.0332 (6)	−0.0063 (4)	0.0148 (4)	−0.0012 (5)
C31	0.0255 (5)	0.0217 (5)	0.0222 (5)	0.0015 (4)	0.0119 (4)	0.0007 (4)
C32	0.0296 (5)	0.0321 (6)	0.0208 (5)	0.0031 (4)	0.0110 (4)	−0.0012 (4)
C33	0.0251 (5)	0.0328 (6)	0.0223 (5)	0.0035 (4)	0.0077 (4)	0.0019 (4)
C34	0.0235 (5)	0.0246 (5)	0.0269 (5)	0.0029 (4)	0.0119 (4)	0.0007 (4)
C35	0.0282 (5)	0.0378 (6)	0.0231 (5)	0.0043 (4)	0.0095 (4)	−0.0070 (4)
C36	0.0258 (5)	0.0362 (6)	0.0224 (5)	0.0047 (4)	0.0075 (4)	−0.0037 (4)
C37	0.0255 (5)	0.0483 (7)	0.0336 (6)	0.0103 (5)	0.0078 (5)	−0.0015 (5)
C51	0.0206 (4)	0.0241 (5)	0.0183 (4)	−0.0010 (4)	0.0086 (4)	−0.0025 (4)
C52	0.0223 (4)	0.0254 (5)	0.0175 (4)	−0.0009 (4)	0.0071 (4)	−0.0019 (4)
C53	0.0318 (5)	0.0375 (6)	0.0212 (5)	0.0030 (5)	0.0144 (4)	0.0007 (4)
C54	0.0303 (5)	0.0399 (6)	0.0253 (5)	0.0061 (5)	0.0143 (4)	−0.0055 (5)
C55	0.0274 (5)	0.0271 (5)	0.0304 (5)	0.0039 (4)	0.0113 (4)	−0.0045 (4)
C56	0.0258 (5)	0.0247 (5)	0.0249 (5)	−0.0001 (4)	0.0115 (4)	−0.0003 (4)

Geometric parameters (Å, º) top

O1—C34	1.3694 (12)	C31—C32	1.3971 (15)
O1—C37	1.4307 (14)	C31—C36	1.4067 (14)
O2—C52	1.3657 (13)	C32—C33	1.3984 (15)
O2—H2	0.91 (2)	C32—H32	0.9500
N1—C5	1.3711 (12)	C33—C34	1.3937 (15)
N1—N2	1.3711 (11)	C33—H33	0.9500
N1—C11	1.4341 (13)	C34—C35	1.4006 (15)
N2—C3	1.3457 (13)	C35—C36	1.3833 (15)
C3—C4	1.4131 (14)	C35—H35	0.9500
C3—C31	1.4798 (14)	C36—H36	0.9500
C4—C5	1.3790 (14)	C37—H37A	0.9800
C4—H4	0.9500	C37—H37B	0.9800
C5—C51	1.4827 (13)	C37—H37C	0.9800
C11—C12	1.3904 (14)	C51—C56	1.4041 (14)
C11—C16	1.3912 (14)	C51—C52	1.4063 (14)
C12—C13	1.3945 (15)	C52—C53	1.4025 (14)
C12—H12	0.9500	C53—C54	1.3881 (17)
C13—C14	1.3863 (18)	C53—H53	0.9500
C13—H13	0.9500	C54—C55	1.3940 (16)
C14—C15	1.387 (2)	C54—H54	0.9500
C14—H14	0.9500	C55—C56	1.3873 (14)
C15—C16	1.3924 (17)	C55—H55	0.9500
C15—H15	0.9500	C56—H56	0.9500
C16—H16	0.9500

C34—O1—C37	118.12 (9)	C33—C32—H32	119.0
C52—O2—H2	110.0 (12)	C34—C33—C32	119.22 (10)
C5—N1—N2	111.75 (8)	C34—C33—H33	120.4
C5—N1—C11	129.15 (8)	C32—C33—H33	120.4
N2—N1—C11	119.09 (8)	O1—C34—C33	124.86 (10)
C3—N2—N1	105.23 (8)	O1—C34—C35	115.55 (9)
N2—C3—C4	110.50 (9)	C33—C34—C35	119.57 (9)
N2—C3—C31	121.73 (9)	C36—C35—C34	120.59 (10)
C4—C3—C31	127.77 (9)	C36—C35—H35	119.7
C5—C4—C3	106.20 (9)	C34—C35—H35	119.7
C5—C4—H4	126.9	C35—C36—C31	120.92 (10)
C3—C4—H4	126.9	C35—C36—H36	119.5
N1—C5—C4	106.31 (8)	C31—C36—H36	119.5
N1—C5—C51	123.26 (9)	O1—C37—H37A	109.5
C4—C5—C51	130.28 (9)	O1—C37—H37B	109.5
C12—C11—C16	120.92 (10)	H37A—C37—H37B	109.5
C12—C11—N1	119.50 (9)	O1—C37—H37C	109.5
C16—C11—N1	119.58 (9)	H37A—C37—H37C	109.5
C11—C12—C13	119.27 (10)	H37B—C37—H37C	109.5
C11—C12—H12	120.4	C56—C51—C52	118.79 (9)
C13—C12—H12	120.4	C56—C51—C5	120.96 (9)
C14—C13—C12	120.18 (11)	C52—C51—C5	120.18 (9)
C14—C13—H13	119.9	O2—C52—C53	121.86 (9)
C12—C13—H13	119.9	O2—C52—C51	118.34 (9)
C13—C14—C15	120.09 (11)	C53—C52—C51	119.79 (10)
C13—C14—H14	120.0	C54—C53—C52	120.35 (10)
C15—C14—H14	120.0	C54—C53—H53	119.8
C14—C15—C16	120.45 (11)	C52—C53—H53	119.8
C14—C15—H15	119.8	C53—C54—C55	120.25 (10)
C16—C15—H15	119.8	C53—C54—H54	119.9
C11—C16—C15	119.08 (11)	C55—C54—H54	119.9
C11—C16—H16	120.5	C56—C55—C54	119.64 (10)
C15—C16—H16	120.5	C56—C55—H55	120.2
C32—C31—C36	117.71 (9)	C54—C55—H55	120.2
C32—C31—C3	120.64 (9)	C55—C56—C51	121.13 (10)
C36—C31—C3	121.64 (9)	C55—C56—H56	119.4
C31—C32—C33	121.98 (10)	C51—C56—H56	119.4
C31—C32—H32	119.0

C5—N1—N2—C3	−0.35 (11)	C36—C31—C32—C33	−0.50 (16)
C11—N1—N2—C3	178.79 (8)	C3—C31—C32—C33	−179.54 (10)
N1—N2—C3—C4	−0.10 (11)	C31—C32—C33—C34	−0.12 (17)
N1—N2—C3—C31	179.72 (9)	C37—O1—C34—C33	−4.99 (16)
N2—C3—C4—C5	0.51 (12)	C37—O1—C34—C35	176.10 (11)
C31—C3—C4—C5	−179.30 (10)	C32—C33—C34—O1	−178.32 (10)
N2—N1—C5—C4	0.67 (11)	C32—C33—C34—C35	0.54 (17)
C11—N1—C5—C4	−178.37 (9)	O1—C34—C35—C36	178.63 (11)
N2—N1—C5—C51	−175.35 (9)	C33—C34—C35—C36	−0.33 (17)
C11—N1—C5—C51	5.61 (16)	C34—C35—C36—C31	−0.31 (18)
C3—C4—C5—N1	−0.69 (11)	C32—C31—C36—C35	0.72 (17)
C3—C4—C5—C51	174.95 (10)	C3—C31—C36—C35	179.74 (10)
C5—N1—C11—C12	−131.50 (11)	N1—C5—C51—C56	50.34 (14)
N2—N1—C11—C12	49.52 (13)	C4—C5—C51—C56	−124.66 (12)
C5—N1—C11—C16	48.36 (15)	N1—C5—C51—C52	−132.78 (10)
N2—N1—C11—C16	−130.62 (10)	C4—C5—C51—C52	52.22 (15)
C16—C11—C12—C13	−0.83 (16)	C56—C51—C52—O2	179.78 (9)
N1—C11—C12—C13	179.03 (9)	C5—C51—C52—O2	2.83 (14)
C11—C12—C13—C14	0.03 (17)	C56—C51—C52—C53	−1.56 (15)
C12—C13—C14—C15	0.71 (19)	C5—C51—C52—C53	−178.50 (9)
C13—C14—C15—C16	−0.7 (2)	O2—C52—C53—C54	−179.36 (10)
C12—C11—C16—C15	0.87 (17)	C51—C52—C53—C54	2.03 (16)
N1—C11—C16—C15	−178.98 (10)	C52—C53—C54—C55	−0.71 (17)
C14—C15—C16—C11	−0.13 (19)	C53—C54—C55—C56	−1.06 (17)
N2—C3—C31—C32	−163.44 (10)	C54—C55—C56—C51	1.52 (16)
C4—C3—C31—C32	16.36 (16)	C52—C51—C56—C55	−0.20 (15)
N2—C3—C31—C36	17.57 (15)	C5—C51—C56—C55	176.71 (10)
C4—C3—C31—C36	−162.64 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2ⁱ	0.91 (2)	1.88 (2)	2.7894 (11)	175.0 (17)

Symmetry code: (i) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₂
M_r	342.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	9.5880 (5), 13.7397 (8), 14.2771 (7)
β (°)	109.340 (4)
V (Å³)	1774.68 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.33 × 0.31 × 0.26

Data collection
Diffractometer	Stoe IPDS-II two-circle diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24784, 4085, 3676
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.653

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.096, 1.02
No. of reflections	4085
No. of parameters	241
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), 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···N2ⁱ	0.91 (2)	1.88 (2)	2.7894 (11)	175.0 (17)

Symmetry code: (i) x, −y+3/2, z−1/2.

Acknowledgements

AB is grateful to the Higher Education Commission of Pakistan for the grant that supported this work.

References

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