6-Bromo-1-methyl-4-[2-(1-phenyl­ethyl­idene)hydrazinyl­idene]-3,4-dihydro-1H-2λ6,1-benzothia­zine-2,2-dione

Shafiq, M.; Tahir, M.N.; Harrison, W.T.A.; Bukhari, I.H.; Khan, I.U.

doi:10.1107/S1600536812051380

organic compounds

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ISSN: 2056-9890

Volume 69| Part 2| February 2013| Page o164

doi:10.1107/S1600536812051380

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6-Bromo-1-methyl-4-[2-(1-phenylethylidene)hydrazinylidene]-3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione

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

^aDepartment of Chemistry, Government College University, Faisalabad 38000, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Chemistry, University of Aberdeen, Meston 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, C₁₇H₁₆BrN₃O₂S, the dihedral angle between the aromatic rings is 1.24 (15)° and the C=N—N=C torsion angle is 167.7 (3)°. 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 = 0.027 Å). In the crystal, C—H⋯O interactions link the molecules into C(10) [010] chains. A weak C—H⋯π interaction is also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq, Zia-Ur-Rehman et al. (2011 ). For further synthetic details, see: Shafiq, Khan et al. (2011 ).

Experimental

Crystal data

C₁₇H₁₆BrN₃O₂S
M_r = 406.30
Monoclinic, P 2₁ /c
a = 16.4369 (13) Å
b = 6.5400 (5) Å
c = 16.5025 (17) Å
β = 104.312 (4)°
V = 1718.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.53 mm⁻¹
T = 296 K
0.34 × 0.22 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.518, T_max = 0.603
7358 measured reflections
3213 independent reflections
2256 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.082
S = 1.02
3213 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O2ⁱ	0.93	2.49	3.280 (4)	143
C13—H13⋯Cg2ⁱⁱ	0.93	2.65	3.445 (3)	143
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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: 10.1107/S1600536812051380/ng5314sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812051380/ng5314Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812051380/ng5314Isup3.cml

checkCIF report

Comment top

As part of our ongoing studies of benzothiazine derivatives (Shafiq, Zia-Ur-Rehman et al., 2011), we now describe the synthesis and structure of the title compound, (I).

The dihedral angle between the C1–C6 and C10–C15 aromatic rings is 1.24 (15)° and the C7=N1—N2=C9 torsion angle is 167.7 (3)°. The conformation of the C9/C10/C15/C17/N3/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 = 0.027 Å). Atom C16 is displaced from the mean plane by 0.081 (6) Å

In the crystal, C—H···O interactions (Table 1) link the molecules into C(10) chains propagating in [010]. A weak C—H···π interaction is also observed.

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 further synthetic details, see: Shafiq, Khan et al. (2011).

Experimental top

In the synthesis of title compound, 4-hydrazinylidene 6-bromo-1-methyl-3H-2?6,1-benzothiazine-2,2-dione (Shafiq, Khan et al., 2011) was subjected to react with acetophenone according to literature procedure (Shafiq, Zia-Ur-Rehman et al., 2011). The product obtained was then recrystallized in ethyl acetate under slow evaporation to obtain single crystals suitable for X-ray diffraction.

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.

6-Bromo-1-methyl-4-[2-(1-phenylethylidene)hydrazinylidene]- 3,4-dihydro-1H-2λ⁶,1-benzothiazine-2,2-dione top

Crystal data top

C₁₇H₁₆BrN₃O₂S	F(000) = 824
M_r = 406.30	D_x = 1.570 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 305 reflections
a = 16.4369 (13) Å	θ = 3.2–23.6°
b = 6.5400 (5) Å	µ = 2.53 mm⁻¹
c = 16.5025 (17) Å	T = 296 K
β = 104.312 (4)°	Block, yellow
V = 1718.9 (3) Å³	0.34 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3213 independent reflections
Radiation source: fine-focus sealed tube	2256 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 26.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −20→17
T_min = 0.518, T_max = 0.603	k = −8→6
7358 measured reflections	l = −19→20

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0286P)² + 0.9478P] where P = (F_o² + 2F_c²)/3
3213 reflections	(Δ/σ)_max = 0.001
219 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₁₇H₁₆BrN₃O₂S	V = 1718.9 (3) Å³
M_r = 406.30	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.4369 (13) Å	µ = 2.53 mm⁻¹
b = 6.5400 (5) Å	T = 296 K
c = 16.5025 (17) Å	0.34 × 0.22 × 0.20 mm
β = 104.312 (4)°

Data collection top

Bruker APEXII CCD diffractometer	3213 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2256 reflections with I > 2σ(I)
T_min = 0.518, T_max = 0.603	R_int = 0.026
7358 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.082	H-atom parameters constrained
S = 1.02	Δρ_max = 0.56 e Å⁻³
3213 reflections	Δρ_min = −0.51 e Å⁻³
219 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
Br1	0.04673 (2)	1.15885 (6)	−0.08154 (2)	0.06740 (16)
S1	0.43842 (5)	0.75192 (12)	0.12674 (5)	0.0441 (2)
O1	0.42875 (15)	0.6385 (3)	0.05136 (16)	0.0603 (6)
O2	0.51929 (13)	0.7562 (4)	0.18377 (16)	0.0698 (7)
N1	0.23859 (15)	0.4159 (4)	0.17978 (15)	0.0421 (6)
N2	0.21392 (15)	0.5841 (4)	0.12622 (15)	0.0421 (6)
N3	0.40793 (14)	0.9893 (3)	0.10698 (16)	0.0424 (6)
C1	0.20276 (18)	0.1325 (4)	0.25032 (17)	0.0363 (7)
C2	0.28613 (19)	0.1040 (5)	0.29276 (19)	0.0460 (8)
H2	0.3263	0.1985	0.2861	0.055*
C3	0.3104 (2)	−0.0622 (5)	0.3447 (2)	0.0553 (9)
H3	0.3663	−0.0774	0.3735	0.066*
C4	0.2522 (3)	−0.2049 (5)	0.3539 (2)	0.0603 (10)
H4	0.2690	−0.3185	0.3878	0.072*
C5	0.1696 (3)	−0.1800 (5)	0.3132 (2)	0.0636 (10)
H5	0.1301	−0.2761	0.3201	0.076*
C6	0.1443 (2)	−0.0116 (5)	0.2617 (2)	0.0515 (9)
H6	0.0880	0.0047	0.2345	0.062*
C7	0.17779 (18)	0.3127 (4)	0.19519 (18)	0.0373 (7)
C8	0.08710 (19)	0.3642 (5)	0.1633 (2)	0.0640 (10)
H8A	0.0817	0.4895	0.1321	0.096*
H8B	0.0620	0.3802	0.2096	0.096*
H8C	0.0593	0.2561	0.1277	0.096*
C9	0.27553 (17)	0.7046 (4)	0.12489 (17)	0.0345 (7)
C10	0.25885 (17)	0.8882 (4)	0.07144 (16)	0.0325 (7)
C11	0.17668 (17)	0.9302 (4)	0.02748 (17)	0.0386 (7)
H11	0.1338	0.8406	0.0310	0.046*
C12	0.15853 (17)	1.1031 (5)	−0.02113 (18)	0.0396 (7)
C13	0.22109 (19)	1.2375 (5)	−0.02726 (18)	0.0429 (7)
H13	0.2082	1.3552	−0.0595	0.051*
C14	0.30252 (19)	1.1972 (4)	0.01430 (19)	0.0426 (7)
H14	0.3448	1.2874	0.0093	0.051*
C15	0.32298 (17)	1.0237 (4)	0.06383 (17)	0.0338 (7)
C16	0.4731 (2)	1.1389 (5)	0.1033 (3)	0.0671 (11)
H16A	0.4745	1.1602	0.0460	0.101*
H16B	0.5267	1.0888	0.1343	0.101*
H16C	0.4610	1.2659	0.1270	0.101*
C17	0.36293 (17)	0.6705 (5)	0.17760 (19)	0.0445 (8)
H17A	0.3709	0.5261	0.1906	0.053*
H17B	0.3702	0.7444	0.2299	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0446 (2)	0.0784 (3)	0.0729 (3)	0.01094 (18)	0.00247 (17)	0.0328 (2)
S1	0.0363 (4)	0.0360 (5)	0.0626 (5)	0.0044 (3)	0.0170 (4)	0.0088 (4)
O1	0.0730 (16)	0.0413 (15)	0.0809 (17)	0.0003 (11)	0.0461 (13)	−0.0069 (12)
O2	0.0325 (13)	0.0724 (18)	0.0970 (19)	0.0044 (11)	0.0016 (13)	0.0260 (15)
N1	0.0462 (15)	0.0345 (15)	0.0462 (15)	0.0026 (12)	0.0127 (12)	0.0127 (12)
N2	0.0451 (15)	0.0345 (15)	0.0457 (15)	0.0039 (12)	0.0091 (12)	0.0148 (12)
N3	0.0374 (14)	0.0298 (15)	0.0572 (16)	−0.0033 (11)	0.0062 (12)	0.0031 (12)
C1	0.0480 (19)	0.0295 (18)	0.0336 (16)	−0.0005 (13)	0.0145 (14)	−0.0012 (12)
C2	0.049 (2)	0.041 (2)	0.052 (2)	0.0096 (15)	0.0204 (16)	0.0132 (15)
C3	0.057 (2)	0.059 (2)	0.053 (2)	0.0190 (18)	0.0203 (18)	0.0145 (18)
C4	0.102 (3)	0.037 (2)	0.049 (2)	0.017 (2)	0.030 (2)	0.0117 (16)
C5	0.097 (3)	0.042 (2)	0.053 (2)	−0.021 (2)	0.021 (2)	0.0062 (17)
C6	0.056 (2)	0.047 (2)	0.046 (2)	−0.0148 (16)	0.0038 (16)	0.0029 (16)
C7	0.0430 (18)	0.0295 (17)	0.0390 (17)	0.0006 (13)	0.0094 (14)	0.0023 (13)
C8	0.043 (2)	0.058 (2)	0.087 (3)	−0.0007 (16)	0.0081 (19)	0.025 (2)
C9	0.0372 (17)	0.0308 (18)	0.0380 (16)	0.0051 (13)	0.0142 (13)	0.0034 (12)
C10	0.0373 (17)	0.0290 (17)	0.0315 (15)	0.0044 (12)	0.0092 (13)	0.0028 (12)
C11	0.0382 (17)	0.0370 (18)	0.0421 (17)	0.0001 (13)	0.0126 (14)	0.0072 (14)
C12	0.0361 (17)	0.043 (2)	0.0384 (17)	0.0062 (14)	0.0071 (13)	0.0057 (14)
C13	0.053 (2)	0.0322 (18)	0.0419 (18)	0.0047 (15)	0.0085 (15)	0.0085 (14)
C14	0.0467 (19)	0.0301 (18)	0.0496 (19)	−0.0046 (13)	0.0091 (15)	0.0069 (14)
C15	0.0379 (17)	0.0296 (17)	0.0335 (16)	0.0004 (12)	0.0080 (13)	−0.0032 (12)
C16	0.051 (2)	0.042 (2)	0.099 (3)	−0.0104 (16)	0.001 (2)	0.0071 (19)
C17	0.0399 (18)	0.048 (2)	0.0470 (19)	0.0082 (14)	0.0144 (15)	0.0176 (15)

Geometric parameters (Å, º) top

Br1—C12	1.897 (3)	C6—H6	0.9300
S1—O1	1.423 (2)	C7—C8	1.491 (4)
S1—O2	1.427 (2)	C8—H8A	0.9600
S1—N3	1.639 (2)	C8—H8B	0.9600
S1—C17	1.744 (3)	C8—H8C	0.9600
N1—C7	1.282 (4)	C9—C10	1.475 (4)
N1—N2	1.407 (3)	C9—C17	1.501 (4)
N2—C9	1.288 (3)	C10—C11	1.393 (4)
N3—C15	1.420 (3)	C10—C15	1.407 (4)
N3—C16	1.464 (4)	C11—C12	1.376 (4)
C1—C2	1.389 (4)	C11—H11	0.9300
C1—C6	1.391 (4)	C12—C13	1.375 (4)
C1—C7	1.484 (4)	C13—C14	1.370 (4)
C2—C3	1.381 (4)	C13—H13	0.9300
C2—H2	0.9300	C14—C15	1.390 (4)
C3—C4	1.371 (5)	C14—H14	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.369 (5)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C5—C6	1.391 (5)	C17—H17A	0.9700
C5—H5	0.9300	C17—H17B	0.9700

O1—S1—O2	118.12 (15)	H8A—C8—H8C	109.5
O1—S1—N3	110.94 (14)	H8B—C8—H8C	109.5
O2—S1—N3	107.57 (13)	N2—C9—C10	118.5 (3)
O1—S1—C17	108.81 (15)	N2—C9—C17	122.9 (3)
O2—S1—C17	110.25 (15)	C10—C9—C17	118.5 (2)
N3—S1—C17	99.55 (13)	C11—C10—C15	118.7 (2)
C7—N1—N2	114.7 (2)	C11—C10—C9	119.0 (2)
C9—N2—N1	112.6 (2)	C15—C10—C9	122.3 (2)
C15—N3—C16	120.8 (2)	C12—C11—C10	120.5 (3)
C15—N3—S1	117.68 (18)	C12—C11—H11	119.7
C16—N3—S1	116.8 (2)	C10—C11—H11	119.7
C2—C1—C6	118.0 (3)	C13—C12—C11	120.7 (3)
C2—C1—C7	120.3 (3)	C13—C12—Br1	118.9 (2)
C6—C1—C7	121.7 (3)	C11—C12—Br1	120.4 (2)
C3—C2—C1	121.1 (3)	C14—C13—C12	119.7 (3)
C3—C2—H2	119.5	C14—C13—H13	120.1
C1—C2—H2	119.5	C12—C13—H13	120.1
C4—C3—C2	120.2 (3)	C13—C14—C15	121.0 (3)
C4—C3—H3	119.9	C13—C14—H14	119.5
C2—C3—H3	119.9	C15—C14—H14	119.5
C5—C4—C3	120.0 (3)	C14—C15—C10	119.3 (3)
C5—C4—H4	120.0	C14—C15—N3	119.3 (2)
C3—C4—H4	120.0	C10—C15—N3	121.4 (2)
C4—C5—C6	120.3 (3)	N3—C16—H16A	109.5
C4—C5—H5	119.9	N3—C16—H16B	109.5
C6—C5—H5	119.9	H16A—C16—H16B	109.5
C5—C6—C1	120.5 (3)	N3—C16—H16C	109.5
C5—C6—H6	119.8	H16A—C16—H16C	109.5
C1—C6—H6	119.8	H16B—C16—H16C	109.5
N1—C7—C1	115.4 (3)	C9—C17—S1	111.6 (2)
N1—C7—C8	124.9 (3)	C9—C17—H17A	109.3
C1—C7—C8	119.8 (3)	S1—C17—H17A	109.3
C7—C8—H8A	109.5	C9—C17—H17B	109.3
C7—C8—H8B	109.5	S1—C17—H17B	109.3
H8A—C8—H8B	109.5	H17A—C17—H17B	108.0
C7—C8—H8C	109.5

C7—N1—N2—C9	167.7 (3)	N2—C9—C10—C15	−177.5 (3)
O1—S1—N3—C15	60.7 (2)	C17—C9—C10—C15	4.6 (4)
O2—S1—N3—C15	−168.7 (2)	C15—C10—C11—C12	−1.3 (4)
C17—S1—N3—C15	−53.8 (2)	C9—C10—C11—C12	178.2 (3)
O1—S1—N3—C16	−95.2 (3)	C10—C11—C12—C13	0.1 (4)
O2—S1—N3—C16	35.4 (3)	C10—C11—C12—Br1	179.5 (2)
C17—S1—N3—C16	150.3 (3)	C11—C12—C13—C14	1.1 (5)
C6—C1—C2—C3	0.0 (4)	Br1—C12—C13—C14	−178.4 (2)
C7—C1—C2—C3	179.6 (3)	C12—C13—C14—C15	−1.0 (5)
C1—C2—C3—C4	1.3 (5)	C13—C14—C15—C10	−0.2 (4)
C2—C3—C4—C5	−1.7 (5)	C13—C14—C15—N3	−179.0 (3)
C3—C4—C5—C6	0.8 (5)	C11—C10—C15—C14	1.3 (4)
C4—C5—C6—C1	0.5 (5)	C9—C10—C15—C14	−178.1 (3)
C2—C1—C6—C5	−0.8 (5)	C11—C10—C15—N3	−180.0 (2)
C7—C1—C6—C5	179.5 (3)	C9—C10—C15—N3	0.6 (4)
N2—N1—C7—C1	178.9 (2)	C16—N3—C15—C14	3.1 (4)
N2—N1—C7—C8	−2.3 (4)	S1—N3—C15—C14	−151.7 (2)
C2—C1—C7—N1	10.8 (4)	C16—N3—C15—C10	−175.6 (3)
C6—C1—C7—N1	−169.5 (3)	S1—N3—C15—C10	29.5 (3)
C2—C1—C7—C8	−168.0 (3)	N2—C9—C17—S1	146.5 (3)
C6—C1—C7—C8	11.6 (4)	C10—C9—C17—S1	−35.7 (3)
N1—N2—C9—C10	−179.9 (2)	O1—S1—C17—C9	−60.6 (2)
N1—N2—C9—C17	−2.1 (4)	O2—S1—C17—C9	168.4 (2)
N2—C9—C10—C11	3.1 (4)	N3—S1—C17—C9	55.5 (2)
C17—C9—C10—C11	−174.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2ⁱ	0.93	2.49	3.280 (4)	143
C13—H13···Cg2ⁱⁱ	0.93	2.65	3.445 (3)	143

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆BrN₃O₂S
M_r	406.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	16.4369 (13), 6.5400 (5), 16.5025 (17)
β (°)	104.312 (4)
V (Å³)	1718.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.53
Crystal size (mm)	0.34 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.518, 0.603
No. of measured, independent and observed [I > 2σ(I)] reflections	7358, 3213, 2256
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.082, 1.02
No. of reflections	3213
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.51

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
C2—H2···O2ⁱ	0.93	2.49	3.280 (4)	143
C13—H13···Cg2ⁱⁱ	0.93	2.65	3.445 (3)	143

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

Acknowledgements

MS acknowledges the support of HEC Pakistan for the PhD fellowship.

References

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., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011). Asian J. Chem. 23, 2101–2106. CAS 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

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