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

Shafiq, M.; Khan, I.U.; Zia-ur-Rehman, M.; Mahmood, T.; Ashfaq, M.; Ahmad, S.

doi:10.1107/S1600536812025743

organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Page o2100

https://doi.org/10.1107/S1600536812025743

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

Muhammad Shafiq,^a ^* Islam Ullah Khan,^b Muhammad Zia-ur-Rehman,^c Tariq Mahmood,^d Muhammad Ashfaq ^e and Saeed Ahmad ^f

^aDepartment of Chemistry, Government College University, Faisalabad 38040, Pakistan, ^bMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Ferozpur Road, Lahore 54600, Pakistan, ^dDepartment of Chemistry, COMSATS institute of Information Technology, Abbottabad, Pakistan, ^eDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan, and ^fDepartment of Chemistry, Gomal University, Dera Ismail Khan, K.P.K, Pakistan
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 3 June 2012; accepted 6 June 2012; online 13 June 2012)

In the title compound, C₁₇H₁₇N₃O₂S, the phenyl ring is oriented at dihedral angles of 8.5 (2) and 1.17 (14)°, respectively, to the C=N—N plane and the fused aromatic ring. The thiazine ring adopts an envelope conformation with the S atom at the flap. In the crystal, a weak C—H⋯O interaction connects the molecules, forming a helical chain along the a axis.

Related literature

For the synthesis, see: Shafiq et al. (2011 ). For related structures, see: Shafiq et al. (2011a ,b , 2012 ).

Experimental

Crystal data

C₁₇H₁₇N₃O₂S
M_r = 327.40
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.6678 (2) Å
b = 12.0783 (6) Å
c = 20.0529 (8) Å
V = 1614.97 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.38 × 0.11 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.923, T_max = 0.985
9111 measured reflections
3830 independent reflections
2819 reflections with I > 2σ(I)
R_int = 0.030

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.108
S = 0.97
3828 reflections
210 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1577 Friedel pairs
Flack parameter: −0.06 (9)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1ⁱ	0.97	2.56	3.420 (3)	148
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

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, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536812025743/is5153sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812025743/is5153Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812025743/is5153Isup3.cml

checkCIF report

Comment top

The present structure is analogue to 1-ethyl-4-[1-(1-phenylethylidene)-hydrazin-2-ylidene]-3,4-dihydro-1H- 2λ⁶,1-benzothiazine-2,2-dione(II) (Shafiq et al., 2012) and related to 4-hydrazinylidene-1-methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (III) (Shafiq, Khan et al., 2011a) and 6-bromo-1-methyl-4-[2- (4-methylbenzylidene)hydrazinylidene]-3H-2λ⁶, 1-benzothiazine-2,2-dione (IV) (Shafiq, Khan et al., 2011b). The structure of molecule looks planer as the plane generated from atoms (C1–C7/C9–C15/N1) showes an r.m.s. deviation of 0.0365 Å, while atoms S1 and C16 show maximum deviations of 0.702 (2) and -0.256 (4) Å, respectively. The fused aromatic ring and the mean plane of the thiazine ring are oriented at a dihedral angle of 9.34 (14)° and thiazine ring adopted sofa shape with an r.m.s. deviation of 0.233 (2)°. Comparison of dihedral angles between the phenyl and fused aromatic rings in I and II [i.e. 1.17 (14) and 79.33 (2)°, respectively] also explain the planarity of title compound. Similarly dihedral angles between the phenyl and thiazine rings in I and II are 9.34 (2) and 69.74 (6)°, respectively. An intermolecular hydrogen bonding interaction of C—H···O type connects the molecule along the a axis and generates a chain structure (Table 1 and Fig. 2). In the group R₂C=N—N=C(CH₃)Ar, the configurations around the two double bonds are Z and E, respectively.

Related literature top

For the synthesis, see: Shafiq et al. (2011). For related structures, see: Shafiq et al. (2011a,b, 2012).

Experimental top

In the synthesis of title compound, 4-hydrazinylidene-1- methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq, Khan et al., 2011a) was subjected to react with acetophenone according to literature procedure (Shafiq, Zia-ur-Rehman et al., 2011). The product obtained was then recrystallized in ethylacetate under slow evaporation to obtain single crystals suitable for X-ray diffraction.

Structure description top

For the synthesis, see: Shafiq et al. (2011). For related structures, see: Shafiq et al. (2011a,b, 2012).

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 molecular structure of the title compound, with 50% displacement ellipsoids for non-H atoms.
	Fig. 2. A packing diagram, showing C—H···O hydrogen bonds (dashed lines).

1-Methyl-4-[1-(1-phenylethylidene)-hydrazin-2-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 = 1.347 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2415 reflections
a = 6.6678 (2) Å	θ = 2.6–21.1°
b = 12.0783 (6) Å	µ = 0.21 mm⁻¹
c = 20.0529 (8) Å	T = 296 K
V = 1614.97 (11) Å³	Needle, colorless
Z = 4	0.38 × 0.11 × 0.07 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3830 independent reflections
Radiation source: fine-focus sealed tube	2819 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
φ and ω scans	θ_max = 28.3°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→6
T_min = 0.923, T_max = 0.985	k = −16→13
9111 measured reflections	l = −26→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)] = 0.045	H-atom parameters constrained
wR(F²) = 0.108	w = 1/[σ²(F_o²) + (0.0554P)² + 0.0282P] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.007
3828 reflections	Δρ_max = 0.21 e Å⁻³
210 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1577 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (9)

Crystal data top

C₁₇H₁₇N₃O₂S	V = 1614.97 (11) Å³
M_r = 327.40	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6678 (2) Å	µ = 0.21 mm⁻¹
b = 12.0783 (6) Å	T = 296 K
c = 20.0529 (8) Å	0.38 × 0.11 × 0.07 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3830 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2819 reflections with I > 2σ(I)
T_min = 0.923, T_max = 0.985	R_int = 0.030
9111 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.108	Δρ_max = 0.21 e Å⁻³
S = 0.97	Δρ_min = −0.27 e Å⁻³
3828 reflections	Absolute structure: Flack (1983), 1577 Friedel pairs
210 parameters	Absolute structure parameter: −0.06 (9)
0 restraints

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	−0.0436 (3)	0.1646 (2)	0.19872 (12)	0.0434 (6)
C2	−0.1882 (4)	0.1755 (3)	0.24813 (14)	0.0607 (8)
H2	−0.2979	0.2216	0.2412	0.073*
C3	−0.1708 (5)	0.1190 (3)	0.30686 (14)	0.0689 (9)
H3	−0.2704	0.1259	0.3390	0.083*
C4	−0.0087 (5)	0.0522 (3)	0.31910 (14)	0.0703 (9)
H4	0.0036	0.0154	0.3596	0.084*
C5	0.1365 (5)	0.0404 (2)	0.27030 (12)	0.0592 (7)
H5	0.2473	−0.0044	0.2785	0.071*
C6	0.1196 (4)	0.09462 (19)	0.20875 (11)	0.0425 (5)
C7	0.2735 (3)	0.07398 (19)	0.15723 (11)	0.0401 (5)
C8	0.2426 (3)	0.12341 (18)	0.08901 (11)	0.0394 (5)
H8A	0.1559	0.0756	0.0629	0.047*
H8B	0.3705	0.1291	0.0662	0.047*
C9	0.6894 (3)	−0.07684 (19)	0.12801 (12)	0.0448 (6)
C10	0.8400 (3)	−0.08935 (19)	0.07412 (12)	0.0446 (6)
C11	0.8205 (4)	−0.0311 (2)	0.01409 (12)	0.0485 (6)
H11	0.7109	0.0153	0.0078	0.058*
C12	0.9605 (4)	−0.0414 (2)	−0.03551 (13)	0.0573 (7)
H12	0.9457	−0.0014	−0.0748	0.069*
C13	1.1223 (4)	−0.1103 (3)	−0.02763 (15)	0.0666 (8)
H13	1.2158	−0.1178	−0.0617	0.080*
C14	1.1456 (4)	−0.1680 (3)	0.03080 (16)	0.0723 (8)
H14	1.2560	−0.2141	0.0365	0.087*
C15	1.0061 (4)	−0.1578 (2)	0.08111 (15)	0.0571 (7)
H15	1.0234	−0.1975	0.1204	0.068*
C16	0.6984 (5)	−0.1505 (3)	0.18763 (15)	0.0859 (11)
H16A	0.6132	−0.1214	0.2220	0.129*
H16B	0.8339	−0.1541	0.2037	0.129*
H16C	0.6538	−0.2234	0.1756	0.129*
C17	−0.2573 (3)	0.2746 (2)	0.12031 (13)	0.0601 (8)
H17A	−0.3647	0.2230	0.1275	0.090*
H17B	−0.2542	0.2957	0.0742	0.090*
H17C	−0.2782	0.3391	0.1474	0.090*
N1	−0.0679 (3)	0.22309 (19)	0.13822 (10)	0.0543 (6)
N2	0.4234 (3)	0.01227 (18)	0.17172 (10)	0.0500 (5)
N3	0.5596 (3)	−0.00040 (18)	0.11964 (10)	0.0508 (5)
O1	0.0707 (2)	0.29407 (17)	0.03230 (9)	0.0663 (6)
O2	0.2661 (2)	0.32168 (14)	0.13476 (9)	0.0559 (5)
S1	0.13459 (7)	0.25435 (5)	0.09576 (3)	0.04299 (16)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0355 (12)	0.0530 (15)	0.0417 (13)	−0.0110 (11)	0.0034 (10)	−0.0029 (11)
C2	0.0496 (15)	0.073 (2)	0.0592 (17)	−0.0102 (14)	0.0168 (12)	−0.0038 (15)
C3	0.072 (2)	0.080 (2)	0.0548 (18)	−0.0237 (17)	0.0264 (15)	−0.0051 (16)
C4	0.103 (2)	0.063 (2)	0.0452 (16)	−0.0274 (18)	0.0170 (17)	0.0015 (14)
C5	0.0776 (17)	0.0510 (16)	0.0489 (16)	−0.0075 (15)	0.0031 (15)	0.0062 (12)
C6	0.0466 (13)	0.0416 (13)	0.0392 (12)	−0.0097 (11)	0.0021 (11)	−0.0003 (10)
C7	0.0427 (12)	0.0382 (12)	0.0395 (13)	−0.0067 (10)	0.0019 (10)	0.0023 (10)
C8	0.0385 (12)	0.0417 (12)	0.0380 (12)	−0.0005 (9)	0.0027 (10)	0.0002 (11)
C9	0.0459 (13)	0.0354 (13)	0.0531 (14)	−0.0007 (10)	−0.0081 (11)	0.0037 (11)
C10	0.0443 (13)	0.0360 (12)	0.0536 (14)	−0.0027 (10)	−0.0086 (11)	−0.0010 (10)
C11	0.0454 (13)	0.0447 (15)	0.0555 (16)	0.0030 (11)	−0.0077 (11)	0.0006 (12)
C12	0.0661 (17)	0.0553 (17)	0.0506 (16)	−0.0018 (14)	−0.0047 (14)	−0.0050 (13)
C13	0.0637 (17)	0.067 (2)	0.0694 (19)	0.0017 (16)	0.0120 (16)	−0.0144 (17)
C14	0.0625 (17)	0.064 (2)	0.090 (2)	0.0226 (16)	0.0003 (18)	−0.0040 (17)
C15	0.0568 (15)	0.0448 (15)	0.0695 (18)	0.0119 (12)	−0.0036 (14)	0.0044 (13)
C16	0.096 (2)	0.080 (2)	0.081 (2)	0.0307 (19)	0.0198 (18)	0.0376 (19)
C17	0.0329 (12)	0.075 (2)	0.0724 (18)	0.0058 (12)	−0.0040 (11)	−0.0046 (15)
N1	0.0322 (9)	0.0787 (17)	0.0521 (12)	0.0092 (10)	0.0048 (8)	0.0099 (12)
N2	0.0512 (12)	0.0504 (13)	0.0486 (12)	0.0059 (10)	0.0022 (9)	0.0078 (10)
N3	0.0485 (11)	0.0534 (13)	0.0506 (13)	0.0095 (10)	0.0044 (9)	0.0074 (10)
O1	0.0577 (10)	0.0845 (15)	0.0567 (11)	0.0191 (10)	0.0038 (9)	0.0243 (10)
O2	0.0494 (9)	0.0457 (10)	0.0726 (12)	−0.0038 (8)	0.0088 (9)	−0.0036 (9)
S1	0.0344 (3)	0.0471 (3)	0.0475 (3)	0.0042 (3)	0.0046 (2)	0.0087 (3)

Geometric parameters (Å, º) top

C1—C2	1.389 (3)	C10—C11	1.400 (3)
C1—C6	1.392 (3)	C11—C12	1.369 (3)
C1—N1	1.413 (3)	C11—H11	0.9300
C2—C3	1.366 (4)	C12—C13	1.371 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.371 (4)	C13—C14	1.372 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C14—C15	1.378 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.402 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.477 (3)	C16—H16B	0.9600
C7—N2	1.280 (3)	C16—H16C	0.9600
C7—C8	1.507 (3)	C17—N1	1.453 (3)
C8—S1	1.743 (2)	C17—H17A	0.9600
C8—H8A	0.9700	C17—H17B	0.9600
C8—H8B	0.9700	C17—H17C	0.9600
C9—N3	1.277 (3)	N1—S1	1.6402 (19)
C9—C10	1.483 (3)	N2—N3	1.392 (3)
C9—C16	1.491 (3)	O1—S1	1.4251 (18)
C10—C15	1.389 (3)	O2—S1	1.4288 (18)

C2—C1—C6	119.8 (2)	C11—C12—C13	120.5 (3)
C2—C1—N1	119.0 (2)	C11—C12—H12	119.8
C6—C1—N1	121.14 (19)	C13—C12—H12	119.8
C3—C2—C1	120.6 (3)	C14—C13—C12	119.7 (3)
C3—C2—H2	119.7	C14—C13—H13	120.1
C1—C2—H2	119.7	C12—C13—H13	120.1
C2—C3—C4	121.0 (3)	C13—C14—C15	120.2 (3)
C2—C3—H3	119.5	C13—C14—H14	119.9
C4—C3—H3	119.5	C15—C14—H14	119.9
C3—C4—C5	119.1 (3)	C14—C15—C10	121.1 (3)
C3—C4—H4	120.5	C14—C15—H15	119.4
C5—C4—H4	120.5	C10—C15—H15	119.4
C4—C5—C6	121.2 (3)	C9—C16—H16A	109.5
C4—C5—H5	119.4	C9—C16—H16B	109.5
C6—C5—H5	119.4	H16A—C16—H16B	109.5
C1—C6—C5	118.3 (2)	C9—C16—H16C	109.5
C1—C6—C7	123.0 (2)	H16A—C16—H16C	109.5
C5—C6—C7	118.8 (2)	H16B—C16—H16C	109.5
N2—C7—C6	118.8 (2)	N1—C17—H17A	109.5
N2—C7—C8	122.9 (2)	N1—C17—H17B	109.5
C6—C7—C8	118.23 (19)	H17A—C17—H17B	109.5
C7—C8—S1	110.21 (16)	N1—C17—H17C	109.5
C7—C8—H8A	109.6	H17A—C17—H17C	109.5
S1—C8—H8A	109.6	H17B—C17—H17C	109.5
C7—C8—H8B	109.6	C1—N1—C17	121.73 (19)
S1—C8—H8B	109.6	C1—N1—S1	117.79 (15)
H8A—C8—H8B	108.1	C17—N1—S1	119.25 (17)
N3—C9—C10	115.9 (2)	C7—N2—N3	113.76 (19)
N3—C9—C16	124.3 (2)	C9—N3—N2	115.0 (2)
C10—C9—C16	119.7 (2)	O1—S1—O2	118.72 (12)
C15—C10—C11	117.4 (2)	O1—S1—N1	107.15 (10)
C15—C10—C9	121.8 (2)	O2—S1—N1	110.61 (11)
C11—C10—C9	120.8 (2)	O1—S1—C8	111.07 (12)
C12—C11—C10	121.0 (2)	O2—S1—C8	107.78 (10)
C12—C11—H11	119.5	N1—S1—C8	99.87 (11)
C10—C11—H11	119.5

C6—C1—C2—C3	0.7 (4)	C11—C12—C13—C14	−1.0 (4)
N1—C1—C2—C3	179.1 (2)	C12—C13—C14—C15	0.7 (5)
C1—C2—C3—C4	1.4 (5)	C13—C14—C15—C10	−0.2 (5)
C2—C3—C4—C5	−1.5 (5)	C11—C10—C15—C14	−0.1 (4)
C3—C4—C5—C6	−0.5 (4)	C9—C10—C15—C14	−179.5 (2)
C2—C1—C6—C5	−2.6 (3)	C2—C1—N1—C17	−13.5 (4)
N1—C1—C6—C5	179.0 (2)	C6—C1—N1—C17	164.9 (2)
C2—C1—C6—C7	176.5 (2)	C2—C1—N1—S1	153.8 (2)
N1—C1—C6—C7	−1.8 (3)	C6—C1—N1—S1	−27.8 (3)
C4—C5—C6—C1	2.5 (4)	C6—C7—N2—N3	−179.38 (19)
C4—C5—C6—C7	−176.7 (2)	C8—C7—N2—N3	2.9 (3)
C1—C6—C7—N2	176.9 (2)	C10—C9—N3—N2	−178.1 (2)
C5—C6—C7—N2	−3.9 (3)	C16—C9—N3—N2	1.0 (4)
C1—C6—C7—C8	−5.3 (3)	C7—N2—N3—C9	−167.5 (2)
C5—C6—C7—C8	173.8 (2)	C1—N1—S1—O1	169.67 (19)
N2—C7—C8—S1	−145.02 (19)	C17—N1—S1—O1	−22.8 (2)
C6—C7—C8—S1	37.3 (2)	C1—N1—S1—O2	−59.5 (2)
N3—C9—C10—C15	170.5 (2)	C17—N1—S1—O2	108.0 (2)
C16—C9—C10—C15	−8.7 (4)	C1—N1—S1—C8	53.8 (2)
N3—C9—C10—C11	−8.9 (3)	C17—N1—S1—C8	−138.6 (2)
C16—C9—C10—C11	172.0 (3)	C7—C8—S1—O1	−169.41 (15)
C15—C10—C11—C12	−0.2 (4)	C7—C8—S1—O2	58.95 (17)
C9—C10—C11—C12	179.2 (2)	C7—C8—S1—N1	−56.59 (17)
C10—C11—C12—C13	0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1ⁱ	0.97	2.56	3.420 (3)	148

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇N₃O₂S
M_r	327.40
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.6678 (2), 12.0783 (6), 20.0529 (8)
V (Å³)	1614.97 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.38 × 0.11 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.923, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	9111, 3830, 2819
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.108, 0.97
No. of reflections	3828
No. of parameters	210
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.27
Absolute structure	Flack (1983), 1577 Friedel pairs
Absolute structure parameter	−0.06 (9)

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
C8—H8B···O1ⁱ	0.97	2.56	3.420 (3)	148

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

MS acknowledges the Higher Education Commission of Pakistan for financial support, GC University Lahore, Pakistan for laboratory facilities during his PhD studies and Dr Michael Harmata for guidance during a visit to his laboratory at the University of Missouri, USA.

References

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