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

Badshah, A.; Hasan, A.; Barbarín, C.R.; Zia, M.

doi:10.1107/S1600536808017054

organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page o1264

doi:10.1107/S1600536808017054

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

Amir Badshah,^a Aurangzeb Hasan,^a ^* Cecilia R. Barbarín ^b and Mehwash Zia ^a

^aDepartment of Chemistry, Quaid-i-Azam University, Islamabad 45320, Pakistan, and ^bDivisión de Estudios de Posgrado, Facultad de Ciencias Químicas, U.A.N.L., Guerreo y Progreso S/N, Col. Treviño, C.P. 64570, Monterrey, NL, Mexico
^*Correspondence e-mail: flavonoids@hotmail.com

(Received 21 May 2008; accepted 5 June 2008; online 13 June 2008)

The title compound, C₂₁H₁₆N₂O₂, 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].

Related literature

For related literature, see: Ahmad et al. (1990 , 1997 ); Beeam et al. (1984 ); Elguero (1983 ); Trofinenko (1972 ).

Experimental

Crystal data

C₂₁H₁₆N₂O₂
M_r = 328.36
Monoclinic, P 2₁ /c
a = 10.793 (3) Å
b = 12.948 (3) Å
c = 11.705 (3) Å
β = 93.508 (14)°
V = 1632.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.44 × 0.40 × 0.26 mm

Data collection

Siemens P4 diffractometer
Absorption correction: none
5767 measured reflections
3720 independent reflections
2353 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 97 reflections intensity decay: 3.6%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.128
S = 1.03
3720 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: XSCANS (Siemens, 1999 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808017054/lh2632sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017054/lh2632Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

For related literature, see: Ahmad et al. (1990, 1997); Beeam et al. (1984); Elguero (1983); Trofinenko (1972).

Experimental top

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).

Computing details top

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).

Figures top

	Fig. 1. The molecular structure of (III) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (III) showing the hydrogen bonds as dashed lines.
	Fig. 3. Reaction scheme.

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

Crystal data top

C₂₁H₁₆N₂O₂	F(000) = 688
M_r = 328.36	D_x = 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	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 27.5°, θ_min = 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(F_o²) + (0.0468P)² + 0.4416P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3720 reflections	Δρ_max = 0.15 e Å⁻³
227 parameters	Δρ_min = −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
M_r = 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	R_int = 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	Δρ_max = 0.15 e Å⁻³
3720 reflections	Δρ_min = −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	U_iso*/U_eq
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
M_r	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
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: XSCANS (Siemens, 1999), SHELXTL-Plus (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

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.

Acknowledgements

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

References

Ahmad, R., Malik, M. A. & Zia-ul-Haq, M. (1990). J. Chem. Soc. Pak. 12, 352–355. Google Scholar
Ahmad, R., Zia-ul-Haq, M., Duddeek, H., Stefaniak, L. & Kowski, J. S. (1997). Monatsh. Chem. 128, 633–640. CrossRef CAS Web of Science Google Scholar
Beeam, C. F., Hall, H. L., Huff, A. M., Tummons, R. C. & Grady, S. A. O. (1984). J. Heteroatom. Chem. 21, 1897–1902. Google Scholar
Bonati, F. (1980). Chim. Ind. (Roma), 62, 323–328,. CAS Google Scholar
Elguero, J. (1983). Comprehensive Heterocyclic Chemistry, Vol. 5, Part 4A, pp. 167, 304. Elmford, New York: Pergamon Press. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1999). XSCANS User's Manual. Siemens Analytical X-Ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Trofinenko, S. (1972). Chem. Rev. 72, 497–500. Google Scholar