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

Shafiq, M.; Khan, I.U.; Zia-ur-Rehman, M.; Arshad, M.N.; Asiri, A.M.

doi:10.1107/S1600536811028406

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2092

doi:10.1107/S1600536811028406

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

Muhammad Shafiq,^a Islam Ullah Khan,^a ^* Muhammad Zia-ur-Rehman,^b Muhammad Nadeem Arshad ^c ^*‡ and Abdullah M. Asiri ^d

^aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^bApplied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan, ^cX-ray Diffraction and Physical Laboratory, Department of Physics, School of Physical Sciences, University of the Punjab, Quaid-e-Azam Campus, Lahore 54590, Pakistan, and ^dThe Center of Excellence for Advanced Materials Research, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia
^*Correspondence e-mail: iukhan@gcu.edu.pk, mnachemist@hotmail.com

(Received 11 July 2011; accepted 15 July 2011; online 23 July 2011)

In the title compound, C₁₇H₁₆BrN₃O₂S, the two fused rings are twisted by a dihedral angle of 6.61 (15)°. The thiazine ring adopts a sofa conformation. The toluene ring is oriented at dihedral angles of 15.5 (2) and 20.6 (2)° with respect to the bromobenzene and thiazine rings, respectively. The benzylidene system is approximately planar [r.m.s. deviation = 0.0388 Å]. In the cyrstal, weak intermolecular C—H⋯O hydrogen bonds connects the molecules into a chain along the b axis.

Related literature

For the synthesis of the title compound, see: Shafiq et al. (2011 ). For related structures, see: Khan et al. (2010 ); Shafiq et al. (2009 ); Arshad et al. (2009 ).

Experimental

Crystal data

C₁₇H₁₆BrN₃O₂S
M_r = 406.30
Monoclinic, P 2₁
a = 9.1077 (6) Å
b = 6.8328 (4) Å
c = 14.1765 (9) Å
β = 96.807 (3)°
V = 876.00 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.48 mm⁻¹
T = 296 K
0.32 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.504, T_max = 0.790
10166 measured reflections
4119 independent reflections
2881 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.078
S = 0.97
4119 reflections
220 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ), 1771 Friedel pairs
Flack parameter: 0.004 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯O1ⁱ	0.96	2.64	3.546 (5)	158
Symmetry code: (i) $[-x+2, y+{\script{1\over 2}}, -z]$ .

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: PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811028406/pv2429sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811028406/pv2429Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811028406/pv2429Isup3.cml

checkCIF report

Comment top

In the title molecule (Fig. 1), the thiazine ring adopts a sofa conformation which is similar to the conformation of the corresponding ring in a previously reported compoud, 1-propyl-1H-2,1-benzothiazin-4(3H)-one 2,2-dioxide (Khan et al., 2010). The aromatic ring (C1—C6) in the title compound is twisted at 15.5 (2)° with respect to the touluene ring (C10—C15). The benzylidene moiety (C9—C16/N1/N2) is also very near to planerity as showing the r. m. s. deviation of 0.0388Å and is oriented at a dihedral angle 15.02 (12)° with respect to the benzene ring (C1—C6). The fused aromatic (C1—C6) and thiazine (C1/C6/C7/C8/N1/S1) rings are twisted at a dihedral angle 6.61 (15)°. The oxygen atom from SO₂ group is involved in weak C—H···O type hydrogen bonding interaction, which connects the molecules in a zig-zag mode along the b-axis.

The crystal structures of several molecules related to the title compound have been reported (Arshad et al., 2009; Shafiq et al., 2009).

Related literature top

For the synthesis of the title compound, see: Shafiq et al. (2011). For related structures, see: Khan et al. (2010); Shafiq et al. (2009); Arshad et al. (2009).

Experimental top

The synthesis of the title compound has already been reportrd (Shafiq et al., 2011). It was recrystalized from a solution in dry ethanol.

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: PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The ORTEP diagram of the title molecule showing the thermal ellipsoids drawn at 50% probability level.
	Fig. 2. A unit cell diagram of the title compound showing C—H···O type interactions using dashed lines.

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

Crystal data top

C₁₇H₁₆BrN₃O₂S	F(000) = 412
M_r = 406.30	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3801 reflections
a = 9.1077 (6) Å	θ = 2.3–23.7°
b = 6.8328 (4) Å	µ = 2.48 mm⁻¹
c = 14.1765 (9) Å	T = 296 K
β = 96.807 (3)°	Needle, yellow
V = 876.00 (10) Å³	0.32 × 0.12 × 0.10 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD diffractometer	4119 independent reflections
Radiation source: fine-focus sealed tube	2881 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −12→12
T_min = 0.504, T_max = 0.790	k = −8→9
10166 measured reflections	l = −18→18

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)] = 0.034	H-atom parameters constrained
wR(F²) = 0.078	w = 1/[σ²(F_o²) + (0.0256P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.018
4119 reflections	Δρ_max = 0.29 e Å⁻³
220 parameters	Δρ_min = −0.36 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1771 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.004 (8)

Crystal data top

C₁₇H₁₆BrN₃O₂S	V = 876.00 (10) Å³
M_r = 406.30	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 9.1077 (6) Å	µ = 2.48 mm⁻¹
b = 6.8328 (4) Å	T = 296 K
c = 14.1765 (9) Å	0.32 × 0.12 × 0.10 mm
β = 96.807 (3)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4119 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2881 reflections with I > 2σ(I)
T_min = 0.504, T_max = 0.790	R_int = 0.026
10166 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	H-atom parameters constrained
wR(F²) = 0.078	Δρ_max = 0.29 e Å⁻³
S = 0.97	Δρ_min = −0.36 e Å⁻³
4119 reflections	Absolute structure: Flack (1983), 1771 Friedel pairs
220 parameters	Absolute structure parameter: 0.004 (8)
1 restraint

Special details top

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
Br1	1.13358 (4)	1.44957 (7)	0.45270 (2)	0.08174 (14)
S1	0.72100 (10)	1.11072 (10)	0.03233 (5)	0.0611 (2)
O1	0.8404 (3)	0.9855 (3)	0.02125 (18)	0.0855 (8)
O2	0.6089 (3)	1.1379 (5)	−0.04538 (16)	0.0999 (9)
N1	0.7821 (3)	1.3277 (3)	0.06656 (16)	0.0589 (6)
N2	0.7702 (3)	0.9100 (3)	0.28328 (17)	0.0519 (6)
N3	0.6650 (3)	0.7615 (3)	0.26789 (18)	0.0556 (6)
C1	0.8667 (3)	1.3470 (4)	0.1553 (2)	0.0464 (6)
C2	0.9579 (4)	1.5101 (4)	0.1724 (2)	0.0590 (8)
H2	0.9654	1.5998	0.1238	0.071*
C3	1.0369 (4)	1.5402 (4)	0.2599 (2)	0.0625 (8)
H3	1.0959	1.6509	0.2707	0.075*
C4	1.0285 (3)	1.4062 (4)	0.3312 (2)	0.0539 (7)
C5	0.9427 (3)	1.2426 (4)	0.31626 (19)	0.0472 (7)
H5	0.9405	1.1516	0.3648	0.057*
C6	0.8585 (3)	1.2109 (4)	0.22905 (18)	0.0422 (6)
C7	0.7585 (3)	1.0412 (4)	0.21833 (19)	0.0430 (6)
C8	0.6452 (3)	1.0352 (4)	0.13283 (19)	0.0529 (7)
H8A	0.5630	1.1198	0.1430	0.063*
H8B	0.6077	0.9029	0.1235	0.063*
C9	0.6761 (3)	0.6340 (4)	0.3337 (2)	0.0497 (7)
H9	0.7494	0.6483	0.3847	0.060*
C10	0.5776 (3)	0.4669 (4)	0.33129 (17)	0.0448 (6)
C11	0.4620 (3)	0.4417 (5)	0.25878 (18)	0.0513 (6)
H11	0.4457	0.5356	0.2112	0.062*
C12	0.3723 (4)	0.2815 (4)	0.2565 (2)	0.0572 (8)
H12	0.2944	0.2689	0.2082	0.069*
C13	0.3960 (4)	0.1366 (4)	0.3257 (2)	0.0607 (8)
C14	0.5088 (4)	0.1620 (4)	0.3977 (2)	0.0614 (8)
H14	0.5244	0.0681	0.4454	0.074*
C15	0.5999 (3)	0.3245 (4)	0.4010 (2)	0.0562 (7)
H15	0.6763	0.3382	0.4503	0.067*
C16	0.2981 (4)	−0.0437 (6)	0.3201 (3)	0.0892 (11)
H16A	0.3586	−0.1589	0.3278	0.134*
H16B	0.2389	−0.0476	0.2594	0.134*
H16C	0.2347	−0.0387	0.3695	0.134*
C17	0.7742 (4)	1.4824 (6)	−0.0046 (3)	0.0913 (12)
H17A	0.7455	1.6028	0.0230	0.137*
H17B	0.7025	1.4480	−0.0572	0.137*
H17C	0.8693	1.4984	−0.0264	0.137*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0823 (2)	0.0930 (2)	0.0655 (2)	−0.0207 (2)	−0.00971 (15)	−0.02718 (19)
S1	0.0823 (6)	0.0609 (4)	0.0395 (4)	−0.0132 (4)	0.0050 (4)	−0.0079 (3)
O1	0.1165 (19)	0.0679 (16)	0.0801 (16)	−0.0059 (15)	0.0453 (14)	−0.0163 (13)
O2	0.135 (2)	0.106 (2)	0.0500 (14)	−0.0347 (17)	−0.0242 (15)	0.0036 (13)
N1	0.0768 (18)	0.0526 (13)	0.0453 (13)	−0.0107 (13)	−0.0011 (12)	0.0057 (11)
N2	0.0566 (14)	0.0422 (13)	0.0553 (14)	−0.0149 (11)	−0.0005 (11)	0.0018 (11)
N3	0.0606 (16)	0.0462 (13)	0.0585 (15)	−0.0122 (11)	0.0003 (12)	0.0013 (11)
C1	0.0480 (17)	0.0447 (14)	0.0479 (16)	−0.0029 (12)	0.0112 (13)	−0.0047 (12)
C2	0.069 (2)	0.0496 (17)	0.0604 (19)	−0.0148 (15)	0.0168 (16)	0.0001 (13)
C3	0.063 (2)	0.0513 (16)	0.074 (2)	−0.0220 (14)	0.0096 (17)	−0.0113 (16)
C4	0.0504 (16)	0.0603 (19)	0.0498 (16)	−0.0115 (14)	0.0015 (12)	−0.0193 (14)
C5	0.0506 (17)	0.0493 (15)	0.0419 (15)	−0.0055 (12)	0.0064 (13)	−0.0036 (12)
C6	0.0419 (16)	0.0429 (13)	0.0422 (14)	−0.0058 (12)	0.0077 (12)	−0.0066 (11)
C7	0.0435 (16)	0.0438 (13)	0.0420 (14)	−0.0043 (12)	0.0063 (12)	−0.0083 (12)
C8	0.0521 (18)	0.0549 (15)	0.0515 (17)	−0.0131 (13)	0.0055 (14)	−0.0046 (13)
C9	0.0485 (16)	0.0483 (15)	0.0516 (16)	−0.0026 (13)	0.0036 (13)	−0.0007 (13)
C10	0.0486 (15)	0.0410 (13)	0.0463 (14)	0.0012 (14)	0.0120 (11)	0.0020 (13)
C11	0.0622 (17)	0.0427 (13)	0.0493 (14)	−0.0018 (17)	0.0083 (13)	0.0008 (15)
C12	0.060 (2)	0.0536 (16)	0.0583 (17)	−0.0074 (15)	0.0075 (15)	−0.0110 (15)
C13	0.064 (2)	0.0451 (15)	0.076 (2)	−0.0061 (15)	0.0235 (18)	−0.0048 (15)
C14	0.067 (2)	0.0470 (16)	0.073 (2)	−0.0025 (15)	0.0199 (18)	0.0145 (15)
C15	0.0551 (19)	0.0550 (16)	0.0592 (18)	0.0025 (15)	0.0101 (14)	0.0057 (15)
C16	0.088 (2)	0.0594 (18)	0.123 (3)	−0.027 (2)	0.025 (2)	−0.007 (3)
C17	0.094 (3)	0.085 (3)	0.089 (3)	−0.005 (2)	−0.015 (2)	0.034 (2)

Geometric parameters (Å, º) top

Br1—C4	1.892 (3)	C8—H8A	0.9700
S1—O1	1.407 (3)	C8—H8B	0.9700
S1—O2	1.423 (3)	C9—C10	1.450 (4)
S1—N1	1.637 (3)	C9—H9	0.9300
S1—C8	1.734 (3)	C10—C15	1.384 (4)
N1—C1	1.402 (4)	C10—C11	1.392 (4)
N1—C17	1.457 (4)	C11—C12	1.364 (4)
N2—C7	1.281 (3)	C11—H11	0.9300
N2—N3	1.394 (3)	C12—C13	1.392 (4)
N3—C9	1.271 (3)	C12—H12	0.9300
C1—C2	1.394 (4)	C13—C14	1.371 (5)
C1—C6	1.408 (4)	C13—C16	1.518 (5)
C2—C3	1.374 (4)	C14—C15	1.384 (4)
C2—H2	0.9300	C14—H14	0.9300
C3—C4	1.373 (4)	C15—H15	0.9300
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.366 (4)	C16—H16B	0.9600
C5—C6	1.392 (4)	C16—H16C	0.9600
C5—H5	0.9300	C17—H17A	0.9600
C6—C7	1.471 (4)	C17—H17B	0.9600
C7—C8	1.496 (4)	C17—H17C	0.9600

O1—S1—O2	119.10 (17)	S1—C8—H8B	109.5
O1—S1—N1	110.09 (15)	H8A—C8—H8B	108.1
O2—S1—N1	107.38 (15)	N3—C9—C10	121.9 (3)
O1—S1—C8	107.40 (14)	N3—C9—H9	119.1
O2—S1—C8	110.87 (15)	C10—C9—H9	119.1
N1—S1—C8	100.39 (13)	C15—C10—C11	118.3 (3)
C1—N1—C17	122.0 (3)	C15—C10—C9	119.9 (3)
C1—N1—S1	118.89 (18)	C11—C10—C9	121.7 (3)
C17—N1—S1	117.7 (2)	C12—C11—C10	121.0 (3)
C7—N2—N3	113.6 (2)	C12—C11—H11	119.5
C9—N3—N2	113.0 (2)	C10—C11—H11	119.5
C2—C1—N1	118.9 (3)	C11—C12—C13	120.7 (3)
C2—C1—C6	118.8 (3)	C11—C12—H12	119.6
N1—C1—C6	122.2 (2)	C13—C12—H12	119.6
C3—C2—C1	120.9 (3)	C14—C13—C12	118.4 (3)
C3—C2—H2	119.5	C14—C13—C16	121.7 (3)
C1—C2—H2	119.5	C12—C13—C16	119.9 (3)
C2—C3—C4	119.7 (3)	C13—C14—C15	121.3 (3)
C2—C3—H3	120.1	C13—C14—H14	119.3
C4—C3—H3	120.1	C15—C14—H14	119.3
C5—C4—C3	120.8 (3)	C14—C15—C10	120.2 (3)
C5—C4—Br1	119.2 (2)	C14—C15—H15	119.9
C3—C4—Br1	120.0 (2)	C10—C15—H15	119.9
C4—C5—C6	120.7 (3)	C13—C16—H16A	109.5
C4—C5—H5	119.7	C13—C16—H16B	109.5
C6—C5—H5	119.7	H16A—C16—H16B	109.5
C5—C6—C1	119.0 (2)	C13—C16—H16C	109.5
C5—C6—C7	118.9 (2)	H16A—C16—H16C	109.5
C1—C6—C7	122.0 (2)	H16B—C16—H16C	109.5
N2—C7—C6	118.7 (2)	N1—C17—H17A	109.5
N2—C7—C8	123.6 (2)	N1—C17—H17B	109.5
C6—C7—C8	117.7 (2)	H17A—C17—H17B	109.5
C7—C8—S1	110.75 (19)	N1—C17—H17C	109.5
C7—C8—H8A	109.5	H17A—C17—H17C	109.5
S1—C8—H8A	109.5	H17B—C17—H17C	109.5
C7—C8—H8B	109.5

O1—S1—N1—C1	−64.2 (3)	N3—N2—C7—C6	177.0 (2)
O2—S1—N1—C1	164.7 (2)	N3—N2—C7—C8	−1.1 (4)
C8—S1—N1—C1	48.8 (2)	C5—C6—C7—N2	−11.9 (4)
O1—S1—N1—C17	102.5 (3)	C1—C6—C7—N2	171.1 (3)
O2—S1—N1—C17	−28.6 (3)	C5—C6—C7—C8	166.3 (2)
C8—S1—N1—C17	−144.5 (3)	C1—C6—C7—C8	−10.6 (4)
C7—N2—N3—C9	−178.8 (2)	N2—C7—C8—S1	−139.9 (2)
C17—N1—C1—C2	−6.8 (4)	C6—C7—C8—S1	41.9 (3)
S1—N1—C1—C2	159.2 (2)	O1—S1—C8—C7	58.5 (2)
C17—N1—C1—C6	170.8 (3)	O2—S1—C8—C7	−169.9 (2)
S1—N1—C1—C6	−23.1 (4)	N1—S1—C8—C7	−56.6 (2)
N1—C1—C2—C3	176.7 (3)	N2—N3—C9—C10	−179.8 (2)
C6—C1—C2—C3	−1.1 (4)	N3—C9—C10—C15	175.6 (3)
C1—C2—C3—C4	1.3 (5)	N3—C9—C10—C11	−2.7 (4)
C2—C3—C4—C5	0.2 (5)	C15—C10—C11—C12	0.3 (4)
C2—C3—C4—Br1	−178.6 (2)	C9—C10—C11—C12	178.6 (3)
C3—C4—C5—C6	−1.8 (4)	C10—C11—C12—C13	−1.4 (4)
Br1—C4—C5—C6	177.0 (2)	C11—C12—C13—C14	2.1 (4)
C4—C5—C6—C1	2.0 (4)	C11—C12—C13—C16	−178.0 (3)
C4—C5—C6—C7	−175.1 (2)	C12—C13—C14—C15	−1.7 (4)
C2—C1—C6—C5	−0.5 (4)	C16—C13—C14—C15	178.4 (3)
N1—C1—C6—C5	−178.2 (2)	C13—C14—C15—C10	0.6 (4)
C2—C1—C6—C7	176.5 (2)	C11—C10—C15—C14	0.1 (4)
N1—C1—C6—C7	−1.2 (4)	C9—C10—C15—C14	−178.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···O1ⁱ	0.96	2.64	3.546 (5)	158

Symmetry code: (i) −x+2, y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆BrN₃O₂S
M_r	406.30
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	9.1077 (6), 6.8328 (4), 14.1765 (9)
β (°)	96.807 (3)
V (Å³)	876.00 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.48
Crystal size (mm)	0.32 × 0.12 × 0.10

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.504, 0.790
No. of measured, independent and observed [I > 2σ(I)] reflections	10166, 4119, 2881
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.078, 0.97
No. of reflections	4119
No. of parameters	220
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.36
Absolute structure	Flack (1983), 1771 Friedel pairs
Absolute structure parameter	0.004 (8)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17C···O1ⁱ	0.96	2.64	3.546 (5)	158.0

Symmetry code: (i) −x+2, y+1/2, −z.

Footnotes

‡Materials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan.

Acknowledgements

MS and MNA acknowledge the Higher Education commission of Pakistan for providing sholarships under its indigenous and IRSIP schemes.

References

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