3-Chloro-1-methyl-4-[2-(3-phenyl­allyl­idene)hydrazinyl­idene]-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Khan, I.U.; Shafique, S.

doi:10.1107/S1600536812051513

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o165

doi:10.1107/S1600536812051513

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3-Chloro-1-methyl-4-[2-(3-phenylallylidene)hydrazinylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a ^* M. Nawaz Tahir,^b William T. A. Harrison,^c Islam Ullah Khan ^d and Sidra Shafique ^d

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Chemistry, University of Aberdeen, Mston Walk, Aberdeen AB24 3UE, Scotland, and ^dMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 19 December 2012; accepted 20 December 2012; online 4 January 2013)

In the title compound, C₁₈H₁₆ClN₃O₂S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N—C—C—C = 179.2 (4)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by −0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thiazine ring plane. In the crystal, inversion dimers linked by pairs of C—H⋯O interactions generate R₂²(20) loops and further C—H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π–π stacking interactions [centroid–centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a ). For further synthetic details, see: Shafiq et al. (2011b ).

Experimental

Crystal data

C₁₈H₁₆ClN₃O₂S
M_r = 373.85
Monoclinic, P 2₁ /c
a = 7.2262 (5) Å
b = 13.5823 (9) Å
c = 17.9818 (12) Å
β = 97.023 (4)°
V = 1751.6 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.32 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.895, T_max = 0.939
8051 measured reflections
3107 independent reflections
1808 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.201
S = 1.03
3107 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.93	2.51	3.345 (6)	150
C15—H15⋯O2ⁱⁱ	0.93	2.57	3.464 (6)	161
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812051513/bq2381sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051513/bq2381Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051513/bq2381Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of benzothiazine derivatives with potential biactivity (Shafiq et al., 2011a,b), we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C1–C6 and C13–C18 aromatic rings is 4.81 (2)° and the C9=N2—N3=C10 torsion angle is -178.1 (4)°. The linking alkyl chain takes on an extended conformation [N3—C10—C11—C12 = 179.2 (4)°]. The conformation of the C1/C6/C8/C9/N1/S1 thiazine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). Atom C16 is displaced from the mean plane by 0.343 (6) Å and Cl1, in an axial site, is displaced by 1.761 (4) Å. Atom C8 is a stereogenic centre (R configuration in the arbitrarily-chosen asymmetric unit), but crystal symmetry generates a racemic mixture.

In the crystal, inversion dimers linked by pairs of C—H···O interactions (Table 1) to generate R₂²(20) loops. Further C—H···O bonds link the dimers into (001) sheets. Weak aromatic π-π stacking interactions between the C1—C6 and C13—C18 benzene rings [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

Related literature top

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a). For further synthetic details, see: Shafiq et al. (2011b).

Experimental top

The Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and trans cinnamaldehyde was prepared using the methods reported previously (Shafiq et al., 2011a). The chlorination of the Schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011b). The crude product was recrystallized from ethyl acetate solution to obtain yellow blocks of the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 50% probability level.

3-Chloro-1-methyl-4-[2-(3-phenylallylidene)hydrazinylidene]- 3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₈H₁₆ClN₃O₂S	F(000) = 776
M_r = 373.85	D_x = 1.418 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 305 reflections
a = 7.2262 (5) Å	θ = 3.5–24.5°
b = 13.5823 (9) Å	µ = 0.35 mm⁻¹
c = 17.9818 (12) Å	T = 296 K
β = 97.023 (4)°	Rod, yellow
V = 1751.6 (2) Å³	0.32 × 0.20 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3107 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.895, T_max = 0.939	k = −13→16
8051 measured reflections	l = −21→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.201	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.1036P)² + 0.2998P] where P = (F_o² + 2F_c²)/3
3107 reflections	(Δ/σ)_max < 0.001
227 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₈H₁₆ClN₃O₂S	V = 1751.6 (2) Å³
M_r = 373.85	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.2262 (5) Å	µ = 0.35 mm⁻¹
b = 13.5823 (9) Å	T = 296 K
c = 17.9818 (12) Å	0.32 × 0.20 × 0.18 mm
β = 97.023 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3107 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	1808 reflections with I > 2σ(I)
T_min = 0.895, T_max = 0.939	R_int = 0.043
8051 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.201	H-atom parameters constrained
S = 1.03	Δρ_max = 0.97 e Å⁻³
3107 reflections	Δρ_min = −0.36 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.

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
C1	0.2953 (5)	0.2779 (3)	0.6118 (2)	0.0406 (11)
C2	0.3170 (6)	0.3399 (4)	0.6745 (3)	0.0526 (12)
H2	0.3146	0.4077	0.6673	0.063*
C3	0.3415 (7)	0.3037 (4)	0.7460 (3)	0.0601 (14)
H3	0.3549	0.3465	0.7867	0.072*
C4	0.3463 (7)	0.2037 (4)	0.7574 (3)	0.0622 (14)
H4	0.3660	0.1791	0.8059	0.075*
C5	0.3225 (7)	0.1399 (4)	0.6983 (3)	0.0584 (13)
H5	0.3231	0.0724	0.7069	0.070*
C6	0.2973 (6)	0.1759 (3)	0.6248 (2)	0.0422 (11)
C7	0.3297 (8)	0.0041 (3)	0.5761 (3)	0.0762 (17)
H7A	0.4520	0.0003	0.6036	0.114*
H7B	0.3302	−0.0271	0.5282	0.114*
H7C	0.2419	−0.0286	0.6036	0.114*
C8	0.2780 (6)	0.2531 (3)	0.4704 (3)	0.0422 (11)
H8	0.2142	0.2856	0.4257	0.051*
C9	0.2729 (5)	0.3201 (3)	0.5368 (2)	0.0381 (10)
C10	0.2243 (6)	0.5395 (3)	0.4480 (3)	0.0507 (12)
H10	0.2233	0.5762	0.4916	0.061*
C11	0.2092 (6)	0.5897 (3)	0.3787 (3)	0.0489 (12)
H11	0.2116	0.5542	0.3345	0.059*
C12	0.1917 (6)	0.6871 (3)	0.3759 (3)	0.0480 (12)
H12	0.1893	0.7181	0.4219	0.058*
C13	0.1756 (6)	0.7522 (3)	0.3107 (3)	0.0450 (11)
C14	0.1646 (7)	0.7194 (4)	0.2366 (3)	0.0563 (13)
H14	0.1665	0.6522	0.2266	0.068*
C15	0.1508 (7)	0.7866 (5)	0.1777 (3)	0.0634 (14)
H15	0.1434	0.7639	0.1287	0.076*
C16	0.1482 (7)	0.8848 (5)	0.1912 (3)	0.0683 (15)
H16	0.1402	0.9291	0.1515	0.082*
C17	0.1573 (7)	0.9191 (4)	0.2634 (3)	0.0638 (14)
H17	0.1536	0.9864	0.2725	0.077*
C18	0.1717 (6)	0.8543 (3)	0.3220 (3)	0.0517 (12)
H18	0.1791	0.8786	0.3706	0.062*
S1	0.15957 (18)	0.14181 (8)	0.48575 (7)	0.0514 (4)
O1	0.1890 (5)	0.0698 (2)	0.42999 (19)	0.0666 (10)
O2	−0.0251 (4)	0.1739 (2)	0.49385 (18)	0.0542 (9)
N1	0.2763 (5)	0.1075 (3)	0.5651 (2)	0.0518 (10)
N2	0.2523 (5)	0.4134 (3)	0.5278 (2)	0.0478 (10)
N3	0.2393 (5)	0.4455 (3)	0.4536 (2)	0.0526 (10)
Cl1	0.51237 (17)	0.22812 (9)	0.45547 (8)	0.0621 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.043 (2)	0.041 (3)	0.039 (3)	0.0041 (18)	0.0078 (19)	−0.002 (2)
C2	0.064 (3)	0.050 (3)	0.044 (3)	0.006 (2)	0.007 (2)	−0.006 (3)
C3	0.071 (3)	0.075 (4)	0.034 (3)	0.009 (3)	0.006 (2)	−0.016 (3)
C4	0.066 (3)	0.082 (4)	0.038 (3)	0.007 (3)	0.007 (2)	0.009 (3)
C5	0.071 (3)	0.054 (3)	0.049 (3)	0.006 (2)	0.004 (2)	0.013 (3)
C6	0.049 (3)	0.040 (3)	0.038 (3)	0.0043 (19)	0.006 (2)	0.004 (2)
C7	0.116 (5)	0.035 (3)	0.074 (4)	0.008 (3)	−0.004 (3)	0.004 (3)
C8	0.058 (3)	0.032 (2)	0.037 (3)	0.0042 (18)	0.009 (2)	−0.001 (2)
C9	0.045 (2)	0.028 (2)	0.041 (3)	0.0045 (17)	0.0049 (19)	−0.003 (2)
C10	0.063 (3)	0.038 (3)	0.051 (3)	0.002 (2)	0.006 (2)	0.000 (2)
C11	0.065 (3)	0.036 (3)	0.047 (3)	0.001 (2)	0.010 (2)	0.002 (2)
C12	0.060 (3)	0.038 (3)	0.046 (3)	−0.003 (2)	0.010 (2)	0.000 (2)
C13	0.046 (3)	0.042 (3)	0.046 (3)	−0.0007 (18)	0.003 (2)	0.000 (2)
C14	0.065 (3)	0.049 (3)	0.055 (4)	−0.001 (2)	0.008 (2)	−0.009 (3)
C15	0.061 (3)	0.088 (4)	0.039 (3)	−0.009 (3)	0.001 (2)	0.002 (3)
C16	0.065 (3)	0.080 (4)	0.061 (4)	−0.002 (3)	0.010 (3)	0.024 (3)
C17	0.072 (3)	0.046 (3)	0.073 (4)	−0.003 (2)	0.011 (3)	0.016 (3)
C18	0.065 (3)	0.042 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	0.003 (2)
S1	0.0683 (9)	0.0383 (7)	0.0475 (8)	−0.0027 (5)	0.0070 (6)	−0.0040 (6)
O1	0.109 (3)	0.0401 (19)	0.052 (2)	−0.0042 (17)	0.0127 (19)	−0.0149 (17)
O2	0.0472 (19)	0.060 (2)	0.055 (2)	−0.0051 (14)	0.0033 (15)	−0.0113 (17)
N1	0.081 (3)	0.031 (2)	0.042 (3)	0.0058 (17)	0.0017 (19)	0.0016 (19)
N2	0.066 (3)	0.038 (2)	0.039 (2)	0.0037 (16)	0.0049 (18)	0.0004 (18)
N3	0.076 (3)	0.035 (2)	0.046 (3)	0.0026 (18)	0.0063 (19)	0.0018 (19)
Cl1	0.0630 (8)	0.0605 (8)	0.0664 (10)	0.0036 (5)	0.0223 (6)	−0.0108 (7)

Geometric parameters (Å, º) top

C1—C2	1.401 (6)	C10—C11	1.414 (6)
C1—C6	1.405 (6)	C10—H10	0.9300
C1—C9	1.455 (6)	C11—C12	1.329 (6)
C2—C3	1.368 (7)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.462 (6)
C3—C4	1.373 (7)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.398 (7)
C4—C5	1.365 (7)	C13—C18	1.402 (6)
C4—H4	0.9300	C14—C15	1.393 (7)
C5—C6	1.399 (6)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.357 (7)
C6—N1	1.415 (6)	C15—H15	0.9300
C7—N1	1.463 (6)	C16—C17	1.373 (7)
C7—H7A	0.9600	C16—H16	0.9300
C7—H7B	0.9600	C17—C18	1.366 (6)
C7—H7C	0.9600	C17—H17	0.9300
C8—C9	1.506 (6)	C18—H18	0.9300
C8—S1	1.775 (4)	S1—O2	1.428 (3)
C8—Cl1	1.780 (4)	S1—O1	1.435 (3)
C8—H8	0.9800	S1—N1	1.634 (4)
C9—N2	1.283 (5)	N2—N3	1.397 (5)
C10—N3	1.284 (5)

C2—C1—C6	117.4 (4)	C12—C11—C10	120.7 (5)
C2—C1—C9	119.8 (4)	C12—C11—H11	119.7
C6—C1—C9	122.8 (4)	C10—C11—H11	119.7
C3—C2—C1	122.0 (5)	C11—C12—C13	129.1 (5)
C3—C2—H2	119.0	C11—C12—H12	115.4
C1—C2—H2	119.0	C13—C12—H12	115.4
C2—C3—C4	119.5 (5)	C14—C13—C18	117.0 (4)
C2—C3—H3	120.2	C14—C13—C12	124.0 (4)
C4—C3—H3	120.2	C18—C13—C12	119.0 (4)
C5—C4—C3	120.9 (5)	C15—C14—C13	120.4 (5)
C5—C4—H4	119.5	C15—C14—H14	119.8
C3—C4—H4	119.5	C13—C14—H14	119.8
C4—C5—C6	120.2 (5)	C16—C15—C14	120.7 (5)
C4—C5—H5	119.9	C16—C15—H15	119.7
C6—C5—H5	119.9	C14—C15—H15	119.7
C5—C6—C1	120.0 (4)	C15—C16—C17	120.2 (5)
C5—C6—N1	118.5 (4)	C15—C16—H16	119.9
C1—C6—N1	121.5 (4)	C17—C16—H16	119.9
N1—C7—H7A	109.5	C18—C17—C16	120.0 (5)
N1—C7—H7B	109.5	C18—C17—H17	120.0
H7A—C7—H7B	109.5	C16—C17—H17	120.0
N1—C7—H7C	109.5	C17—C18—C13	121.8 (5)
H7A—C7—H7C	109.5	C17—C18—H18	119.1
H7B—C7—H7C	109.5	C13—C18—H18	119.1
C9—C8—S1	109.4 (3)	O2—S1—O1	120.0 (2)
C9—C8—Cl1	110.5 (3)	O2—S1—N1	112.8 (2)
S1—C8—Cl1	110.3 (2)	O1—S1—N1	108.1 (2)
C9—C8—H8	108.9	O2—S1—C8	103.3 (2)
S1—C8—H8	108.9	O1—S1—C8	110.9 (2)
Cl1—C8—H8	108.9	N1—S1—C8	99.9 (2)
N2—C9—C1	120.3 (4)	C6—N1—C7	121.7 (4)
N2—C9—C8	120.7 (4)	C6—N1—S1	118.1 (3)
C1—C9—C8	119.1 (4)	C7—N1—S1	119.4 (3)
N3—C10—C11	123.1 (5)	C9—N2—N3	115.0 (4)
N3—C10—H10	118.5	C10—N3—N2	112.4 (4)
C11—C10—H10	118.5

C6—C1—C2—C3	0.8 (6)	C14—C15—C16—C17	−0.7 (8)
C9—C1—C2—C3	−178.9 (4)	C15—C16—C17—C18	0.9 (8)
C1—C2—C3—C4	0.4 (7)	C16—C17—C18—C13	−0.7 (7)
C2—C3—C4—C5	−1.5 (7)	C14—C13—C18—C17	0.2 (7)
C3—C4—C5—C6	1.5 (7)	C12—C13—C18—C17	179.9 (4)
C4—C5—C6—C1	−0.4 (7)	C9—C8—S1—O2	60.3 (3)
C4—C5—C6—N1	178.9 (4)	Cl1—C8—S1—O2	−178.0 (2)
C2—C1—C6—C5	−0.8 (6)	C9—C8—S1—O1	−170.0 (3)
C9—C1—C6—C5	178.9 (4)	Cl1—C8—S1—O1	−48.2 (3)
C2—C1—C6—N1	180.0 (4)	C9—C8—S1—N1	−56.2 (3)
C9—C1—C6—N1	−0.4 (6)	Cl1—C8—S1—N1	65.6 (3)
C2—C1—C9—N2	−7.8 (6)	C5—C6—N1—C7	−16.9 (6)
C6—C1—C9—N2	172.6 (4)	C1—C6—N1—C7	162.4 (4)
C2—C1—C9—C8	171.1 (4)	C5—C6—N1—S1	153.4 (3)
C6—C1—C9—C8	−8.5 (6)	C1—C6—N1—S1	−27.4 (5)
S1—C8—C9—N2	−142.1 (3)	O2—S1—N1—C6	−56.8 (4)
Cl1—C8—C9—N2	96.3 (4)	O1—S1—N1—C6	168.2 (3)
S1—C8—C9—C1	39.1 (5)	C8—S1—N1—C6	52.3 (4)
Cl1—C8—C9—C1	−82.5 (4)	O2—S1—N1—C7	113.7 (4)
N3—C10—C11—C12	179.2 (4)	O1—S1—N1—C7	−21.3 (4)
C10—C11—C12—C13	179.5 (4)	C8—S1—N1—C7	−137.2 (4)
C11—C12—C13—C14	4.2 (7)	C1—C9—N2—N3	177.7 (3)
C11—C12—C13—C18	−175.5 (5)	C8—C9—N2—N3	−1.2 (5)
C18—C13—C14—C15	0.1 (7)	C11—C10—N3—N2	180.0 (4)
C12—C13—C14—C15	−179.5 (4)	C9—N2—N3—C10	−178.1 (4)
C13—C14—C15—C16	0.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.51	3.345 (6)	150
C15—H15···O2ⁱⁱ	0.93	2.57	3.464 (6)	161

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆ClN₃O₂S
M_r	373.85
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.2262 (5), 13.5823 (9), 17.9818 (12)
β (°)	97.023 (4)
V (Å³)	1751.6 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.32 × 0.20 × 0.18

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.895, 0.939
No. of measured, independent and observed [I > 2σ(I)] reflections	8051, 3107, 1808
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.201, 1.03
No. of reflections	3107
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.36

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.93	2.51	3.345 (6)	150
C15—H15···O2ⁱⁱ	0.93	2.57	3.464 (6)	161

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

Acknowledgements

MS acknowledges the HEC Pakistan for granting a PhD fellowship.

References

Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011b). Asian J. Chem. 23, 2101–2106. CAS Google Scholar
Shafiq, M., Zia-Ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011a). JJ. Chil. Chem. Soc. 56, 527–531. CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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