1-[5-(4-Chloro­phen­yl)-3-(4-hy­droxy­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]­ethanone

Fun, H.-K.; Quah, C.K.; Priya, S.; Narayana, B.; Sarojini, B.K.

doi:10.1107/S1600536812006885

organic compounds

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ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o818

doi:10.1107/S1600536812006885

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1-[5-(4-Chlorophenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Hoong-Kun Fun,^a ^*‡ Ching Kheng Quah,^a § S. Priya,^b B. Narayana ^b and B. K. Sarojini ^c

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, and ^cDepartment of Chemistry, P. A. College of Engineering, Nadupadavu, Mangalore 574 153, India
^*Correspondence e-mail: hkfun@usm.my

(Received 14 February 2012; accepted 15 February 2012; online 24 February 2012)

In the title compound, C₁₇H₁₅ClN₂O₂, the benzene rings form dihedral angles of 89.56 (5) and 5.87 (5)° with the mean plane of the pyrazoline ring (r.m.s. deviation = 0.084 Å). The dihedral angle between the two benzene rings is 87.57 (5)°. In the crystal, molecules are linked by O—H⋯O and C—H⋯O hydrogen bonds into a helical chain along the c axis. Between the chains weak C—H⋯N and C—H⋯O interactions are present. The crystal studied was an inversion twin with a domain ratio of 0.72 (4):0.28 (4).

Related literature

For general background to and the biological activities of pyrazolines, see: Samshuddin et al. (2011 ); Sarojini et al. (2010 ). For standard bond-length data, see: Allen et al. (1987 ). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ). For a related structure, see: Fun et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₅ClN₂O₂
M_r = 314.76
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.0213 (2) Å
b = 15.6834 (5) Å
c = 18.6368 (6) Å
V = 1467.67 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.43 × 0.36 × 0.22 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.892, T_max = 0.944
21739 measured reflections
5194 independent reflections
4925 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.082
S = 1.05
5194 reflections
205 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 2089 Friedel pairs
Flack parameter: 0.28 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2ⁱ	0.88 (2)	1.82 (2)	2.6971 (12)	171 (2)
C8—H8A⋯N2ⁱⁱ	0.99	2.56	3.5038 (14)	160
C8—H8B⋯O1ⁱⁱⁱ	0.99	2.52	3.4887 (12)	166
C12—H12A⋯O2ⁱ	0.95	2.51	3.1982 (12)	130
Symmetry codes: (i) $[-x+{\script{3\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006885/is5074sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812006885/is5074Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812006885/is5074Isup3.cml

checkCIF report

Comment top

Pyrazolines have been reported to exhibit a broad spectrum of biological activities including antibacterial, antifungal, antioxidant and analgesic properties (Samshuddin et al., 2011; Sarojini et al., 2010). In continuation of our work on synthesis of pyrazoline derivatives (Fun et al., 2010), the title compound (I) is prepared and its crystal structure is reported.

In the title molecule (Fig. 1), the two benzene rings (C1–C6 and C10–C15) form dihedral angles of 89.56 (5) and 5.87 (5)°, respectively, with the 4,5-dihydro-1H-pyrazole ring (N1/N2/C7-C9). The benzene rings form a dihedral angle of 87.57 (5)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable with a related structure (Fun et al., 2010). The crystal studied was an inversion twin with a domain ratio of 0.28 (4):0.72 (4). In the crystal structure (Fig. 2) molecules are linked via intermolecular O1—H1O1···O2 and C12—H12A···O2 hydrogen bonds (Table 1) into a helical chain along the c axis. Weak C8—H8A···N2 and C8—H8B···O1 are also observed between the chains.

Related literature top

For general background to and the biological activities of pyrazolines, see: Samshuddin et al. (2011); Sarojini et al. (2010). For standard bond-length data, see: Allen et al. (1987). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986). For a related structure, see: Fun et al. (2010).

Experimental top

A mixture of (2E)-3-(4-chlorophenyl)-1-(4-hydroxyphenyl)prop-2-en-1-one (2.58 g, 0.01 mol) and hydrazine hydrate (0.5 ml, 0.01 mol) in 25 ml acetic acid was refluxed for 6 h. The reaction mixture was cooled and poured into 50 ml ice-cold water. The precipitate was collected by filtration and purified by recrystallization from ethanol. The single crystals were grown from DMF by slow evaporation method and yield of the compound was 80% (m.p. : 530 K).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing diagram of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

1-[5-(4-Chlorophenyl)-3-(4-hydroxyphenyl)-4,5-dihydro-1H-pyrazol- 1-yl]ethanone top

Crystal data top

C₁₇H₁₅ClN₂O₂	F(000) = 656
M_r = 314.76	D_x = 1.424 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 9904 reflections
a = 5.0213 (2) Å	θ = 3.4–32.7°
b = 15.6834 (5) Å	µ = 0.27 mm⁻¹
c = 18.6368 (6) Å	T = 100 K
V = 1467.67 (9) Å³	Block, colourless
Z = 4	0.43 × 0.36 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5194 independent reflections
Radiation source: fine-focus sealed tube	4925 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
ϕ and ω scans	θ_max = 32.7°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
T_min = 0.892, T_max = 0.944	k = −23→23
21739 measured reflections	l = −28→28

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	w = 1/[σ²(F_o²) + (0.0486P)² + 0.1907P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
5194 reflections	Δρ_max = 0.33 e Å⁻³
205 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 2089 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.28 (4)

Crystal data top

C₁₇H₁₅ClN₂O₂	V = 1467.67 (9) Å³
M_r = 314.76	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.0213 (2) Å	µ = 0.27 mm⁻¹
b = 15.6834 (5) Å	T = 100 K
c = 18.6368 (6) Å	0.43 × 0.36 × 0.22 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	5194 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	4925 reflections with I > 2σ(I)
T_min = 0.892, T_max = 0.944	R_int = 0.019
21739 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.082	Δρ_max = 0.33 e Å⁻³
S = 1.05	Δρ_min = −0.26 e Å⁻³
5194 reflections	Absolute structure: Flack (1983), 2089 Friedel pairs
205 parameters	Absolute structure parameter: 0.28 (4)
0 restraints

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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 > 2sigma(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
Cl1	0.69906 (7)	0.812228 (18)	0.062645 (13)	0.02929 (7)
O1	0.64339 (19)	0.76579 (5)	0.68963 (4)	0.02423 (17)
O2	0.49802 (19)	1.14641 (5)	0.26805 (4)	0.02311 (16)
N1	0.48592 (19)	1.05034 (5)	0.35670 (4)	0.01842 (16)
N2	0.57563 (19)	1.01940 (5)	0.42259 (4)	0.01797 (16)
C1	0.5989 (2)	0.89416 (6)	0.26375 (5)	0.01860 (17)
H1A	0.6798	0.8854	0.3092	0.022*
C2	0.6960 (2)	0.85102 (6)	0.20404 (5)	0.01995 (18)
H2A	0.8422	0.8129	0.2084	0.024*
C3	0.5754 (2)	0.86468 (6)	0.13803 (5)	0.01985 (19)
C4	0.3600 (2)	0.91916 (7)	0.13069 (5)	0.0213 (2)
H4A	0.2775	0.9270	0.0853	0.026*
C5	0.2664 (2)	0.96220 (6)	0.19103 (5)	0.01969 (18)
H5A	0.1202	1.0002	0.1865	0.024*
C6	0.3843 (2)	0.95017 (6)	0.25775 (5)	0.01623 (16)
C7	0.2786 (2)	0.99601 (6)	0.32343 (5)	0.01790 (17)
H7A	0.1201	1.0313	0.3103	0.021*
C8	0.2094 (2)	0.93621 (6)	0.38672 (5)	0.01917 (17)
H8A	0.0320	0.9497	0.4069	0.023*
H8B	0.2129	0.8757	0.3717	0.023*
C9	0.4279 (2)	0.95519 (6)	0.43990 (5)	0.01668 (16)
C10	0.4788 (2)	0.90758 (6)	0.50616 (5)	0.01641 (16)
C11	0.6865 (2)	0.93201 (6)	0.55202 (5)	0.01882 (17)
H11A	0.7907	0.9807	0.5405	0.023*
C12	0.7424 (2)	0.88630 (6)	0.61378 (5)	0.01932 (18)
H12A	0.8841	0.9036	0.6443	0.023*
C13	0.5895 (2)	0.81446 (6)	0.63127 (5)	0.01882 (17)
C14	0.3774 (2)	0.79110 (7)	0.58721 (6)	0.02158 (19)
H14A	0.2688	0.7438	0.5997	0.026*
C15	0.3245 (2)	0.83700 (6)	0.52498 (5)	0.01973 (18)
H15A	0.1813	0.8201	0.4949	0.024*
C16	0.5891 (2)	1.12119 (6)	0.32603 (5)	0.01928 (18)
C17	0.8134 (3)	1.16620 (7)	0.36378 (6)	0.0243 (2)
H17A	0.9646	1.1723	0.3309	0.037*
H17B	0.8681	1.1329	0.4058	0.037*
H17C	0.7536	1.2228	0.3792	0.037*
H1O1	0.774 (5)	0.7911 (13)	0.7133 (11)	0.056 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03723 (16)	0.03089 (13)	0.01976 (10)	−0.00079 (12)	0.00636 (10)	−0.00525 (9)
O1	0.0309 (4)	0.0200 (3)	0.0218 (3)	−0.0001 (3)	−0.0040 (3)	0.0028 (3)
O2	0.0285 (4)	0.0202 (3)	0.0205 (3)	0.0030 (3)	0.0016 (3)	0.0018 (3)
N1	0.0205 (4)	0.0169 (3)	0.0178 (3)	0.0003 (3)	−0.0021 (3)	−0.0003 (3)
N2	0.0198 (4)	0.0170 (3)	0.0171 (3)	0.0013 (3)	−0.0008 (3)	−0.0004 (3)
C1	0.0185 (4)	0.0194 (4)	0.0179 (4)	0.0021 (4)	−0.0021 (3)	0.0006 (3)
C2	0.0202 (5)	0.0187 (4)	0.0210 (4)	0.0020 (4)	0.0003 (4)	−0.0008 (3)
C3	0.0241 (5)	0.0180 (4)	0.0174 (4)	−0.0041 (4)	0.0032 (4)	−0.0007 (3)
C4	0.0239 (5)	0.0229 (4)	0.0170 (4)	−0.0021 (4)	−0.0023 (4)	0.0017 (3)
C5	0.0192 (4)	0.0204 (4)	0.0195 (4)	0.0018 (4)	−0.0025 (4)	0.0022 (3)
C6	0.0153 (4)	0.0162 (4)	0.0173 (3)	−0.0005 (3)	−0.0008 (3)	0.0007 (3)
C7	0.0159 (4)	0.0186 (4)	0.0192 (3)	0.0019 (4)	−0.0012 (3)	−0.0004 (3)
C8	0.0154 (4)	0.0236 (4)	0.0185 (3)	−0.0011 (4)	0.0005 (3)	−0.0010 (3)
C9	0.0149 (4)	0.0181 (4)	0.0170 (3)	0.0019 (3)	0.0004 (3)	−0.0025 (3)
C10	0.0151 (4)	0.0173 (4)	0.0168 (3)	0.0013 (3)	0.0012 (3)	−0.0014 (3)
C11	0.0193 (4)	0.0187 (4)	0.0184 (4)	−0.0017 (4)	0.0003 (3)	−0.0012 (3)
C12	0.0200 (5)	0.0201 (4)	0.0178 (3)	−0.0006 (4)	−0.0001 (3)	−0.0020 (3)
C13	0.0217 (4)	0.0167 (4)	0.0181 (3)	0.0032 (4)	0.0016 (3)	−0.0015 (3)
C14	0.0222 (5)	0.0185 (4)	0.0240 (4)	−0.0027 (4)	0.0004 (4)	0.0014 (3)
C15	0.0174 (4)	0.0202 (4)	0.0216 (4)	−0.0002 (4)	0.0002 (4)	−0.0004 (3)
C16	0.0232 (5)	0.0154 (4)	0.0192 (4)	0.0024 (4)	0.0044 (4)	−0.0020 (3)
C17	0.0306 (5)	0.0177 (4)	0.0247 (4)	−0.0042 (4)	0.0007 (4)	−0.0025 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.7425 (10)	C7—H7A	1.0000
O1—C13	1.3560 (12)	C8—C9	1.5080 (14)
O1—H1O1	0.88 (2)	C8—H8A	0.9900
O2—C16	1.2382 (13)	C8—H8B	0.9900
N1—C16	1.3527 (13)	C9—C10	1.4656 (13)
N1—N2	1.3951 (11)	C10—C15	1.3961 (14)
N1—C7	1.4812 (14)	C10—C11	1.4018 (14)
N2—C9	1.2917 (13)	C11—C12	1.3847 (13)
C1—C2	1.3906 (14)	C11—H11A	0.9500
C1—C6	1.3947 (14)	C12—C13	1.4019 (15)
C1—H1A	0.9500	C12—H12A	0.9500
C2—C3	1.3878 (14)	C13—C14	1.3937 (15)
C2—H2A	0.9500	C14—C15	1.3906 (14)
C3—C4	1.3853 (17)	C14—H14A	0.9500
C4—C5	1.3932 (14)	C15—H15A	0.9500
C4—H4A	0.9500	C16—C17	1.5039 (17)
C5—C6	1.3901 (13)	C17—H17A	0.9800
C5—H5A	0.9500	C17—H17B	0.9800
C6—C7	1.5156 (13)	C17—H17C	0.9800
C7—C8	1.5464 (14)

C13—O1—H1O1	107.2 (13)	C7—C8—H8B	111.2
C16—N1—N2	122.28 (9)	H8A—C8—H8B	109.2
C16—N1—C7	124.39 (8)	N2—C9—C10	120.49 (9)
N2—N1—C7	113.28 (8)	N2—C9—C8	114.05 (9)
C9—N2—N1	107.79 (8)	C10—C9—C8	125.46 (9)
C2—C1—C6	120.88 (9)	C15—C10—C11	118.46 (9)
C2—C1—H1A	119.6	C15—C10—C9	121.25 (9)
C6—C1—H1A	119.6	C11—C10—C9	120.29 (9)
C3—C2—C1	118.76 (10)	C12—C11—C10	121.07 (10)
C3—C2—H2A	120.6	C12—C11—H11A	119.5
C1—C2—H2A	120.6	C10—C11—H11A	119.5
C4—C3—C2	121.58 (9)	C11—C12—C13	119.89 (10)
C4—C3—Cl1	119.33 (8)	C11—C12—H12A	120.1
C2—C3—Cl1	119.10 (9)	C13—C12—H12A	120.1
C3—C4—C5	118.84 (9)	O1—C13—C14	118.50 (9)
C3—C4—H4A	120.6	O1—C13—C12	121.97 (10)
C5—C4—H4A	120.6	C14—C13—C12	119.53 (9)
C6—C5—C4	120.85 (10)	C15—C14—C13	120.08 (10)
C6—C5—H5A	119.6	C15—C14—H14A	120.0
C4—C5—H5A	119.6	C13—C14—H14A	120.0
C5—C6—C1	119.09 (9)	C14—C15—C10	120.93 (10)
C5—C6—C7	120.59 (9)	C14—C15—H15A	119.5
C1—C6—C7	120.31 (8)	C10—C15—H15A	119.5
N1—C7—C6	111.39 (9)	O2—C16—N1	119.33 (10)
N1—C7—C8	100.81 (7)	O2—C16—C17	122.34 (10)
C6—C7—C8	114.01 (8)	N1—C16—C17	118.33 (9)
N1—C7—H7A	110.1	C16—C17—H17A	109.5
C6—C7—H7A	110.1	C16—C17—H17B	109.5
C8—C7—H7A	110.1	H17A—C17—H17B	109.5
C9—C8—C7	102.60 (8)	C16—C17—H17C	109.5
C9—C8—H8A	111.2	H17A—C17—H17C	109.5
C7—C8—H8A	111.2	H17B—C17—H17C	109.5
C9—C8—H8B	111.2

C16—N1—N2—C9	175.65 (9)	N1—N2—C9—C10	178.41 (8)
C7—N1—N2—C9	−6.89 (11)	N1—N2—C9—C8	−1.56 (11)
C6—C1—C2—C3	0.00 (16)	C7—C8—C9—N2	8.59 (11)
C1—C2—C3—C4	−0.79 (16)	C7—C8—C9—C10	−171.37 (9)
C1—C2—C3—Cl1	178.98 (8)	N2—C9—C10—C15	−178.72 (10)
C2—C3—C4—C5	1.16 (16)	C8—C9—C10—C15	1.24 (15)
Cl1—C3—C4—C5	−178.61 (8)	N2—C9—C10—C11	0.87 (14)
C3—C4—C5—C6	−0.76 (16)	C8—C9—C10—C11	−179.17 (10)
C4—C5—C6—C1	0.00 (15)	C15—C10—C11—C12	1.49 (15)
C4—C5—C6—C7	−178.94 (10)	C9—C10—C11—C12	−178.12 (9)
C2—C1—C6—C5	0.38 (15)	C10—C11—C12—C13	−0.15 (16)
C2—C1—C6—C7	179.32 (9)	C11—C12—C13—O1	177.34 (9)
C16—N1—C7—C6	67.68 (12)	C11—C12—C13—C14	−1.79 (15)
N2—N1—C7—C6	−109.72 (9)	O1—C13—C14—C15	−176.80 (10)
C16—N1—C7—C8	−171.01 (9)	C12—C13—C14—C15	2.36 (16)
N2—N1—C7—C8	11.59 (11)	C13—C14—C15—C10	−1.01 (16)
C5—C6—C7—N1	−120.77 (10)	C11—C10—C15—C14	−0.91 (15)
C1—C6—C7—N1	60.30 (12)	C9—C10—C15—C14	178.69 (10)
C5—C6—C7—C8	125.96 (10)	N2—N1—C16—O2	−178.73 (9)
C1—C6—C7—C8	−52.96 (13)	C7—N1—C16—O2	4.09 (15)
N1—C7—C8—C9	−11.08 (10)	N2—N1—C16—C17	1.74 (15)
C6—C7—C8—C9	108.36 (9)	C7—N1—C16—C17	−175.43 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.88 (2)	1.82 (2)	2.6971 (12)	171 (2)
C8—H8A···N2ⁱⁱ	0.99	2.56	3.5038 (14)	160
C8—H8B···O1ⁱⁱⁱ	0.99	2.52	3.4887 (12)	166
C12—H12A···O2ⁱ	0.95	2.51	3.1982 (12)	130

Symmetry codes: (i) −x+3/2, −y+2, z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₅ClN₂O₂
M_r	314.76
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	5.0213 (2), 15.6834 (5), 18.6368 (6)
V (Å³)	1467.67 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.43 × 0.36 × 0.22

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.892, 0.944
No. of measured, independent and observed [I > 2σ(I)] reflections	21739, 5194, 4925
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.761

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.082, 1.05
No. of reflections	5194
No. of parameters	205
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26
Absolute structure	Flack (1983), 2089 Friedel pairs
Absolute structure parameter	0.28 (4)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2ⁱ	0.88 (2)	1.82 (2)	2.6971 (12)	171 (2)
C8—H8A···N2ⁱⁱ	0.99	2.56	3.5038 (14)	160
C8—H8B···O1ⁱⁱⁱ	0.99	2.52	3.4887 (12)	166
C12—H12A···O2ⁱ	0.95	2.51	3.1982 (12)	130

Symmetry codes: (i) −x+3/2, −y+2, z+1/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: A-5525-2009.

Acknowledgements

The authors would like to thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). BN thanks the UGC for financial assistance through SAP and BSR one-time grant for the purchase of chemicals.

References

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