(4Z)-1-Methyl-4-[(2E)-2-(4-methyl­benzyl­idene)hydrazin-1-yl­idene]-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Harrison, W.T.A.; Khan, I.U.; Ejaz

doi:10.1107/S1600536812039529

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2971

https://doi.org/10.1107/S1600536812039529

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(4Z)-1-Methyl-4-[(2E)-2-(4-methylbenzylidene)hydrazin-1-ylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

Muhammad Shafiq,^a ^* William T. A. Harrison,^b Islam Ullah Khan ^c and Ejaz ^c

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^cMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore 54000, Pakistan
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 11 August 2012; accepted 17 September 2012; online 22 September 2012)

In the title compound, C₁₇H₁₇N₃O₂S, the dihedral angle between the aromatic rings is 6.3 (5)° and the C=N—N=C group is statistically planar [torsion angle = 179.8 (8)°]. The conformation of the thiazine ring is an envelope, with the S atom displaced by 0.823 (9) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.012 Å). In the crystal, C—H⋯O interactions link the molecules into C(5) chains propagating along [101]. The chains are consolidated by weak aromatic π–π stacking between the benzene and toluene rings [centroid-to-centroid separation = 3.826 (5) Å and interplanar angle = 6.3 (4)°].

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011 ). For related structures, see: Shafiq, Khan et al. (2011 ); Shafiq et al. (2012 ). For C—H⋯O interactions, see: Steiner (2006 ). For graph-set nomenclature, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₂S
M_r = 327.40
Monoclinic, P 2₁ /n
a = 7.899 (1) Å
b = 25.061 (3) Å
c = 8.1743 (11) Å
β = 101.114 (9)°
V = 1587.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 K
0.45 × 0.21 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer
13483 measured reflections
2877 independent reflections
1897 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.120
wR(F²) = 0.347
S = 1.15
2877 reflections
215 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯O2ⁱ	0.96	2.59	3.468 (13)	153
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039529/zj2094sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039529/zj2094Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039529/zj2094Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of benzothiazine derivatives with potential biological activity (Shafiq, Zia-ur-Rehman et al., 2011), we now describe the crystal structure of the title compound, (I), (Fig. 1).

The dihedral angle between the aromatic rings (C1–C6 and C10–C15) in (I) is 6.3 (5)° and the C7═N2—N3═C9 torsion angle is 179.8 (8)°. Similar values have been seen in related structures (Shafiq, Khan et al., 2011; Shafiq et al., 2012). The conformation of the thiazine ring in (I) is an envelope, with the S atom displaced by 0.823 (9) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.012 Å). Again, this is similar to the situation in related structures (Shafiq, Khan et al., 2011; Shafiq et al., 2012).

In the crystal of (I) (Fig. 2), weak C—H···O interactions (Steiner, 2006) (Table 1) link the molecules to generate C(5) chains propagating in [101]. The chains are consolidated by weak aromatic π–π stacking between the benzene and toluene rings [centroid-centroid separation = 3.826 (5) Å, inter-planar angle = 6.3 (4)°].

Related literature top

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011). For related structures, see: Shafiq, Khan et al. (2011); Shafiq et al. (2012). For C—H···O interactions, see: Steiner (2006). For graph-set nomenclature, see: Bernstein et al. (1995).

Experimental top

For the synthesis, see: Shafiq, Zia-ur-Rehman et al. (2011). Yellow blades were recrystallized from ethyl acetate. The crystal quality was poor, which may correlate with the rather high residuals.

Structure description top

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-ur-Rehman et al. (2011). For related structures, see: Shafiq, Khan et al. (2011); Shafiq et al. (2012). For C—H···O interactions, see: Steiner (2006). For graph-set nomenclature, see: Bernstein et al. (1995).

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, 1997); 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.
	Fig. 2. Detail of the packing of (I) showing part of a [101] chain of molecules linked by C—H···O hydrogen bonds (double dashed lines) and consolidated by aromatic π–π stacking between the centroids of the benzene and toluene rings (open pink lines). Symmetry codes: (i) -1/2 + x, 3/2 - y, -1/2 + z; (ii) -1 + x, y, -1 + z.

(4Z)-1-Methyl-4-[(2E)-2-(4-methylbenzylidene)hydrazin-1- ylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₇H₁₇N₃O₂S	F(000) = 688
M_r = 327.40	D_x = 1.370 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3678 reflections
a = 7.899 (1) Å	θ = 2.8–24.9°
b = 25.061 (3) Å	µ = 0.22 mm⁻¹
c = 8.1743 (11) Å	T = 296 K
β = 101.114 (9)°	Blade, yellow
V = 1587.8 (3) Å³	0.45 × 0.21 × 0.09 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1897 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 25.3°, θ_min = 2.7°
ω scans	h = −9→9
13483 measured reflections	k = −30→30
2877 independent reflections	l = −9→9

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)] = 0.120	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.347	w = 1/[σ²(F_o²) + (0.0894P)² + 15.6763P] where P = (F_o² + 2F_c²)/3
S = 1.15	(Δ/σ)_max < 0.001
2877 reflections	Δρ_max = 1.44 e Å⁻³
215 parameters	Δρ_min = −0.46 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: 0.011 (3)

Crystal data top

C₁₇H₁₇N₃O₂S	V = 1587.8 (3) Å³
M_r = 327.40	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.899 (1) Å	µ = 0.22 mm⁻¹
b = 25.061 (3) Å	T = 296 K
c = 8.1743 (11) Å	0.45 × 0.21 × 0.09 mm
β = 101.114 (9)°

Data collection top

Bruker APEXII CCD diffractometer	1897 reflections with I > 2σ(I)
13483 measured reflections	R_int = 0.049
2877 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.120	0 restraints
wR(F²) = 0.347	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ²(F_o²) + (0.0894P)² + 15.6763P] where P = (F_o² + 2F_c²)/3
2877 reflections	Δρ_max = 1.44 e Å⁻³
215 parameters	Δρ_min = −0.46 e Å⁻³

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	0.2464 (11)	0.6374 (3)	0.1249 (10)	0.0393 (19)
C2	0.0924 (11)	0.6173 (4)	0.0246 (12)	0.048 (2)
H2	−0.0062	0.6384	0.0023	0.058*
C3	0.0902 (12)	0.5668 (4)	−0.0386 (13)	0.052 (2)
H3	−0.0107	0.5539	−0.1047	0.063*
C4	0.2323 (12)	0.5349 (4)	−0.0072 (12)	0.050 (2)
H4	0.2283	0.5005	−0.0500	0.060*
C5	0.3802 (11)	0.5541 (3)	0.0875 (11)	0.042 (2)
H5	0.4779	0.5326	0.1070	0.050*
C6	0.3899 (10)	0.6050 (3)	0.1561 (10)	0.0329 (17)
C7	0.5555 (10)	0.6233 (3)	0.2611 (10)	0.0378 (19)
C8	0.5629 (11)	0.6777 (3)	0.3398 (11)	0.046 (2)
H8A	0.6805	0.6908	0.3583	0.055*
H8B	0.5283	0.6751	0.4471	0.055*
C9	0.9564 (11)	0.5776 (4)	0.4027 (12)	0.045 (2)
H9	0.928 (13)	0.538 (4)	0.348 (12)	0.07 (3)*
C10	1.1248 (10)	0.5891 (3)	0.5059 (10)	0.0362 (19)
C11	1.1580 (11)	0.6354 (4)	0.5998 (11)	0.045 (2)
H11	1.0710	0.6606	0.5980	0.054*
C12	1.3211 (11)	0.6445 (3)	0.6965 (11)	0.044 (2)
H12	1.3421	0.6755	0.7598	0.053*
C13	1.4514 (11)	0.6077 (4)	0.6988 (11)	0.043 (2)
C14	1.4177 (11)	0.5616 (4)	0.6071 (12)	0.051 (2)
H14	1.5050	0.5365	0.6101	0.062*
C15	1.2550 (10)	0.5515 (4)	0.5095 (10)	0.041 (2)
H15	1.2343	0.5202	0.4480	0.049*
C16	0.0902 (13)	0.7157 (4)	0.2205 (13)	0.059 (3)
H16A	0.0280	0.7308	0.1185	0.089*
H16B	0.1207	0.7435	0.3017	0.089*
H16C	0.0189	0.6899	0.2617	0.089*
C17	1.6295 (12)	0.6184 (5)	0.8015 (14)	0.064 (3)
H17A	1.7116	0.6205	0.7292	0.096*
H17B	1.6610	0.5900	0.8802	0.096*
H17C	1.6284	0.6516	0.8602	0.096*
S1	0.4268 (3)	0.72269 (9)	0.2121 (3)	0.0472 (7)
N1	0.2450 (9)	0.6901 (3)	0.1900 (11)	0.052 (2)
N2	0.6832 (9)	0.5911 (3)	0.2813 (9)	0.0448 (18)
N3	0.8324 (9)	0.6113 (3)	0.3859 (10)	0.0477 (19)
O1	0.4836 (11)	0.7265 (3)	0.0588 (9)	0.069 (2)
O2	0.4100 (10)	0.7710 (2)	0.3007 (9)	0.064 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.038 (5)	0.036 (4)	0.042 (5)	−0.003 (4)	0.004 (4)	0.001 (4)
C2	0.033 (5)	0.049 (5)	0.061 (6)	0.006 (4)	0.004 (4)	0.006 (4)
C3	0.038 (5)	0.050 (6)	0.062 (6)	−0.016 (4)	−0.009 (4)	0.003 (5)
C4	0.057 (6)	0.033 (5)	0.061 (6)	−0.008 (4)	0.016 (5)	−0.011 (4)
C5	0.032 (4)	0.039 (5)	0.054 (5)	0.004 (4)	0.006 (4)	−0.004 (4)
C6	0.031 (4)	0.032 (4)	0.037 (4)	0.000 (3)	0.009 (3)	0.000 (3)
C7	0.036 (4)	0.042 (5)	0.036 (5)	−0.001 (4)	0.007 (4)	−0.001 (4)
C8	0.042 (5)	0.051 (5)	0.043 (5)	−0.001 (4)	0.006 (4)	−0.006 (4)
C9	0.039 (5)	0.047 (5)	0.048 (5)	0.001 (4)	0.010 (4)	−0.004 (4)
C10	0.034 (4)	0.040 (4)	0.035 (4)	0.004 (3)	0.008 (4)	0.006 (3)
C11	0.042 (5)	0.045 (5)	0.051 (5)	0.007 (4)	0.015 (4)	0.000 (4)
C12	0.043 (5)	0.041 (5)	0.046 (5)	−0.003 (4)	0.004 (4)	−0.004 (4)
C13	0.038 (5)	0.050 (5)	0.040 (5)	−0.003 (4)	0.005 (4)	0.011 (4)
C14	0.036 (5)	0.055 (6)	0.062 (6)	0.013 (4)	0.006 (4)	0.000 (5)
C15	0.038 (5)	0.045 (5)	0.040 (5)	0.006 (4)	0.006 (4)	−0.004 (4)
C16	0.067 (7)	0.051 (6)	0.066 (7)	0.013 (5)	0.028 (5)	0.005 (5)
C17	0.034 (5)	0.086 (8)	0.065 (7)	−0.001 (5)	−0.004 (5)	0.013 (6)
S1	0.0551 (15)	0.0354 (12)	0.0503 (14)	−0.0034 (10)	0.0081 (11)	−0.0015 (10)
N1	0.038 (4)	0.040 (4)	0.078 (6)	0.005 (3)	0.010 (4)	−0.012 (4)
N2	0.030 (4)	0.048 (4)	0.053 (5)	−0.001 (3)	0.001 (3)	−0.004 (3)
N3	0.035 (4)	0.054 (5)	0.052 (5)	−0.006 (3)	0.002 (3)	−0.007 (4)
O1	0.099 (6)	0.059 (4)	0.057 (4)	−0.025 (4)	0.033 (4)	0.004 (3)
O2	0.081 (5)	0.037 (3)	0.073 (5)	0.004 (3)	0.010 (4)	−0.013 (3)

Geometric parameters (Å, º) top

C1—C6	1.378 (11)	C10—C15	1.391 (11)
C1—C2	1.421 (12)	C11—C12	1.394 (12)
C1—N1	1.424 (11)	C11—H11	0.9300
C2—C3	1.366 (13)	C12—C13	1.378 (12)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.362 (13)	C13—C14	1.377 (13)
C3—H3	0.9300	C13—C17	1.517 (12)
C4—C5	1.359 (12)	C14—C15	1.398 (12)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.388 (11)	C15—H15	0.9300
C5—H5	0.9300	C16—N1	1.445 (11)
C6—C7	1.493 (11)	C16—H16A	0.9600
C7—N2	1.278 (10)	C16—H16B	0.9600
C7—C8	1.502 (12)	C16—H16C	0.9600
C8—S1	1.757 (9)	C17—H17A	0.9600
C8—H8A	0.9700	C17—H17B	0.9600
C8—H8B	0.9700	C17—H17C	0.9600
C9—N3	1.280 (11)	S1—O1	1.414 (7)
C9—C10	1.459 (12)	S1—O2	1.430 (6)
C9—H9	1.10 (10)	S1—N1	1.632 (8)
C10—C11	1.390 (12)	N2—N3	1.410 (9)

C6—C1—C2	118.7 (7)	C13—C12—C11	120.3 (8)
C6—C1—N1	122.8 (7)	C13—C12—H12	119.8
C2—C1—N1	118.4 (7)	C11—C12—H12	119.8
C3—C2—C1	119.5 (8)	C14—C13—C12	119.3 (8)
C3—C2—H2	120.2	C14—C13—C17	120.8 (9)
C1—C2—H2	120.2	C12—C13—C17	120.0 (9)
C4—C3—C2	121.5 (8)	C13—C14—C15	121.5 (8)
C4—C3—H3	119.2	C13—C14—H14	119.3
C2—C3—H3	119.2	C15—C14—H14	119.3
C5—C4—C3	119.1 (8)	C10—C15—C14	119.0 (8)
C5—C4—H4	120.4	C10—C15—H15	120.5
C3—C4—H4	120.4	C14—C15—H15	120.5
C4—C5—C6	122.0 (8)	N1—C16—H16A	109.5
C4—C5—H5	119.0	N1—C16—H16B	109.5
C6—C5—H5	119.0	H16A—C16—H16B	109.5
C1—C6—C5	119.2 (7)	N1—C16—H16C	109.5
C1—C6—C7	121.6 (7)	H16A—C16—H16C	109.5
C5—C6—C7	119.3 (7)	H16B—C16—H16C	109.5
N2—C7—C6	117.5 (7)	C13—C17—H17A	109.5
N2—C7—C8	123.6 (8)	C13—C17—H17B	109.5
C6—C7—C8	118.9 (7)	H17A—C17—H17B	109.5
C7—C8—S1	111.0 (6)	C13—C17—H17C	109.5
C7—C8—H8A	109.4	H17A—C17—H17C	109.5
S1—C8—H8A	109.4	H17B—C17—H17C	109.5
C7—C8—H8B	109.4	O1—S1—O2	117.9 (4)
S1—C8—H8B	109.4	O1—S1—N1	111.0 (5)
H8A—C8—H8B	108.0	O2—S1—N1	108.3 (4)
N3—C9—C10	121.7 (8)	O1—S1—C8	107.9 (5)
N3—C9—H9	118 (5)	O2—S1—C8	110.4 (4)
C10—C9—H9	120 (5)	N1—S1—C8	99.7 (4)
C11—C10—C15	119.6 (8)	C1—N1—C16	123.0 (8)
C11—C10—C9	122.5 (8)	C1—N1—S1	115.8 (6)
C15—C10—C9	117.9 (8)	C16—N1—S1	120.9 (6)
C10—C11—C12	120.3 (8)	C7—N2—N3	113.4 (7)
C10—C11—H11	119.8	C9—N3—N2	111.1 (7)
C12—C11—H11	119.8

C6—C1—C2—C3	−0.3 (13)	C11—C12—C13—C17	178.7 (8)
N1—C1—C2—C3	−179.7 (9)	C12—C13—C14—C15	1.1 (14)
C1—C2—C3—C4	0.4 (15)	C17—C13—C14—C15	−178.9 (9)
C2—C3—C4—C5	−0.9 (15)	C11—C10—C15—C14	−0.5 (12)
C3—C4—C5—C6	1.3 (14)	C9—C10—C15—C14	179.8 (8)
C2—C1—C6—C5	0.7 (12)	C13—C14—C15—C10	−0.2 (14)
N1—C1—C6—C5	−179.9 (8)	C7—C8—S1—O1	−60.6 (7)
C2—C1—C6—C7	−179.6 (8)	C7—C8—S1—O2	169.2 (6)
N1—C1—C6—C7	−0.3 (12)	C7—C8—S1—N1	55.4 (7)
C4—C5—C6—C1	−1.2 (13)	C6—C1—N1—C16	−153.1 (9)
C4—C5—C6—C7	179.1 (8)	C2—C1—N1—C16	26.3 (13)
C1—C6—C7—N2	−178.7 (8)	C6—C1—N1—S1	32.7 (11)
C5—C6—C7—N2	0.9 (11)	C2—C1—N1—S1	−147.9 (7)
C1—C6—C7—C8	2.5 (11)	O1—S1—N1—C1	57.5 (8)
C5—C6—C7—C8	−177.9 (8)	O2—S1—N1—C1	−171.6 (6)
N2—C7—C8—S1	148.3 (7)	C8—S1—N1—C1	−56.1 (7)
C6—C7—C8—S1	−33.0 (9)	O1—S1—N1—C16	−116.9 (8)
N3—C9—C10—C11	4.0 (13)	O2—S1—N1—C16	14.1 (9)
N3—C9—C10—C15	−176.4 (8)	C8—S1—N1—C16	129.5 (8)
C15—C10—C11—C12	0.3 (13)	C6—C7—N2—N3	−178.3 (7)
C9—C10—C11—C12	179.9 (8)	C8—C7—N2—N3	0.4 (12)
C10—C11—C12—C13	0.6 (13)	C10—C9—N3—N2	−179.7 (7)
C11—C12—C13—C14	−1.3 (13)	C7—N2—N3—C9	179.8 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.96	2.59	3.468 (13)	153

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂S
M_r	327.40
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.899 (1), 25.061 (3), 8.1743 (11)
β (°)	101.114 (9)
V (Å³)	1587.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.45 × 0.21 × 0.09

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13483, 2877, 1897
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.120, 0.347, 1.15
No. of reflections	2877
No. of parameters	215
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0894P)² + 15.6763P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	1.44, −0.46

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16A···O2ⁱ	0.96	2.59	3.468 (13)	153

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Acknowledgements

MS acknowledges the Higher Education Commission of Pakistan for providing a PhD scholarship.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Shafiq, M., Harrison, W. T. A., Khan, I. U., Bukhari, I. H. & Bokhari, T. H. (2012). Acta Cryst. E68, o2643. CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011). Acta Cryst. E67, o2092. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Zia-ur-Rehman, M., Khan, I. U., Arshad, M. N. & Khan, S. A. (2011). J. 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
Steiner, Th. (2006). Crystallogr. Rev. 6, 1–57. CrossRef Google Scholar

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