2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-di­oxo-3,4-dihydro-1H-2,1-benzo­thia­zin-4-yl­idene)hydrazinyl­idene]meth­yl}phenol

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

doi:10.1107/S1600536811055978

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o307

doi:10.1107/S1600536811055978

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2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-dioxo-3,4-dihydro-1H-2,1-benzothiazin-4-ylidene)hydrazinylidene]methyl}phenol

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, ^cDepartment of Chemistry, University of Gujrat, Gujrat 50781, Pakistan, and ^dThe Center of Excellence for Advanced Materials Research and Department of Chemistry, Faculty of Science, King Abdul Aziz University, Jeddah, PO Box 80203, Saudi Arabia
^*Correspondence e-mail: hafizshafique@hotmail.com

(Received 15 December 2011; accepted 28 December 2011; online 7 January 2012)

In the title compound, C₁₆H₁₄ClN₃O₃S, the thiazine ring adopts a sofa (half-chair) conformation, with an r.m.s. deviation from the mean plane of 0.23 Å. The S atom and S-bonded C atom exhibit the maximum deviations from the thiazine mean plane [−0.3976 (12) and 0.3179 (14) Å, respectively]. The conformations around the double bonds in the R₂C=N—N=CHR unit are Z and E. An intramolecular O—H⋯N hydrogen bond with the hydroxy group as donor generates an S(6) ring motif. In the crystal, pairs of weak C—H⋯O interactions connect the molecules, forming inversion dimers.

Related literature

For benzothiazine compounds, see: Shafiq, Khan et al. (2011 ); Shafiq, Zia-ur-Rehman et al. (2011 ). For related structures, see: Shafiq et al. (2011a ,b ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₆H₁₄ClN₃O₃S
M_r = 363.81
Monoclinic, P 2₁ /c
a = 7.0973 (5) Å
b = 12.0957 (7) Å
c = 18.7396 (13) Å
β = 96.058 (4)°
V = 1599.75 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 296 K
0.19 × 0.08 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.930, T_max = 0.973
15526 measured reflections
3977 independent reflections
2200 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.073
wR(F²) = 0.211
S = 1.03
3977 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.13 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯N3	0.82 (7)	1.98 (7)	2.682 (5)	143 (7)
C9—H9⋯O1ⁱ	0.95	2.55	3.394 (5)	148
Symmetry code: (i) -x, -y+1, -z+1.

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 for Windows (Farrugia, 1997 ) and 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/S1600536811055978/bh2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055978/bh2407Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055978/bh2407Isup3.cml

checkCIF report

Comment top

We have recently explored the synthesis of different halogenated benzothiazines (Shafiq, Khan, Arshad et al., 2011), and their Schiff bases (Shafiq, Zia-ur-Rehman et al., 2011). The crystal structure of title compound is being reported in order to study the geometry and different interactions in this class of compounds.

The present structure relates with the already published crystal structures of 4-hydrazinylidene-1-methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq, Khan, Zia-ur-Rehman et al., 2011a) and 6-bromo-1-methyl-4-[2-(4-methylbenzylidene)hydrazinylidene]-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq, Khan, Zia-ur-Rehman et al., 2011b). The two fused rings in the title compound (Fig. 1) are oriented at dihedral angle of 7.49 (5)° and the thiazine ring adopts the sofa shape with r.m.s. deviation of about 0.23 Å, and with the maximum deviations arising from S1 [-0.3721 (21) Å] and C8 [0.3118 (26) Å] atoms. The intramolecular hydrogen bonding interaction of O—H···N type generates a six membered ring S₁¹(6) (Bernstein et al., 1995). A weak C—H···O type interaction connects the molecules to form centrosymmetric dimers and generates R₂²(16) ring motifs (Bernstein et al., 1995; Table 1 and Fig. 2).

The phenol ring is oriented at dihedral angle of 8.17 (4) and 15.58 (5)° with respect to the aromatic ring and thiazine ring, and is twisted by 2.07 (3)° with respect to six membered S(6) ring motif generated through the intramolecular O—H···N hydrogen bond.

Related literature top

For benzothiazine compounds, see: Shafiq, Khan et al. (2011); Shafiq, Zia-ur-Rehman et al. (2011). For related structures, see: Shafiq et al. (2011a,b). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

For the synthesis of title compound, 4-hydrazinylidene-1- methyl-3H-2λ⁶,1-benzothiazine-2,2-dione (Shafiq, Khan, Zia-ur-Rehman et al., 2011a) was subjected to react with salicylaldehyde according to literature procedure (Shafiq, Zia-ur-Rehman et al., 2011). The product obtained was then halogenated following another method (Shafiq, Khan, Arshad et al., 2011). Suitable crystals were produced by slow evaporation of a dry ethylacetate solution.

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 for Windows (Farrugia, 1997) and 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 showing 50% displacement ellipsoids.
	Fig. 2. Perspective view which shows the dimers formed through C—H···O hydrogen bonds (dashed lines).

2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-dioxo-3,4-dihydro- 1H-2,1-benzothiazin-4-ylidene)hydrazinylidene]methyl}phenol top

Crystal data top

C₁₆H₁₄ClN₃O₃S	F(000) = 752
M_r = 363.81	D_x = 1.511 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2110 reflections
a = 7.0973 (5) Å	θ = 2.8–23.7°
b = 12.0957 (7) Å	µ = 0.39 mm⁻¹
c = 18.7396 (13) Å	T = 296 K
β = 96.058 (4)°	Needle, colourless
V = 1599.75 (18) Å³	0.19 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3977 independent reflections
Radiation source: fine-focus sealed tube	2200 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ϕ and ω scans	θ_max = 28.3°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→9
T_min = 0.930, T_max = 0.973	k = −16→16
15526 measured reflections	l = −24→25

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0873P)² + 1.6824P] where P = (F_o² + 2F_c²)/3
3977 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 1.13 e Å⁻³
0 restraints	Δρ_min = −0.38 e Å⁻³
0 constraints

Crystal data top

C₁₆H₁₄ClN₃O₃S	V = 1599.75 (18) Å³
M_r = 363.81	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.0973 (5) Å	µ = 0.39 mm⁻¹
b = 12.0957 (7) Å	T = 296 K
c = 18.7396 (13) Å	0.19 × 0.08 × 0.07 mm
β = 96.058 (4)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3977 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2200 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.973	R_int = 0.061
15526 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.073	0 restraints
wR(F²) = 0.211	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 1.13 e Å⁻³
3977 reflections	Δρ_min = −0.38 e Å⁻³
221 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.51356 (17)	0.73641 (10)	0.42510 (7)	0.0613 (4)
S1	0.16021 (16)	0.83188 (8)	0.46237 (6)	0.0466 (3)
O1	−0.0316 (4)	0.7950 (3)	0.46762 (18)	0.0589 (9)
O2	0.1931 (5)	0.9186 (2)	0.41328 (19)	0.0646 (10)
O3	0.2121 (6)	0.4788 (3)	0.27384 (18)	0.0632 (10)
N1	0.2779 (5)	0.8598 (3)	0.5392 (2)	0.0486 (9)
N2	0.2405 (5)	0.5211 (3)	0.48831 (18)	0.0410 (8)
N3	0.2244 (5)	0.4863 (2)	0.41731 (18)	0.0409 (8)
C1	0.2935 (6)	0.7761 (3)	0.5927 (2)	0.0393 (9)
C2	0.3168 (7)	0.8064 (4)	0.6654 (2)	0.0546 (12)
H2	0.3185	0.8823	0.6784	0.066*
C3	0.3368 (7)	0.7278 (5)	0.7172 (3)	0.0625 (14)
H3	0.3541	0.7496	0.7662	0.075*
C4	0.3327 (7)	0.6172 (4)	0.7003 (2)	0.0576 (12)
H4	0.3462	0.5629	0.7371	0.069*
C5	0.3090 (6)	0.5861 (4)	0.6295 (2)	0.0466 (10)
H5	0.3059	0.5097	0.6178	0.056*
C6	0.2894 (5)	0.6638 (3)	0.5745 (2)	0.0349 (8)
C7	0.2647 (5)	0.6248 (3)	0.4995 (2)	0.0340 (8)
C8	0.2740 (6)	0.7083 (3)	0.4402 (2)	0.0402 (9)
H8	0.2059	0.6776	0.3950	0.048*
C9	0.2063 (6)	0.3806 (3)	0.4143 (2)	0.0399 (9)
H9	0.2041	0.3408	0.4579	0.048*
C10	0.1889 (5)	0.3193 (3)	0.3476 (2)	0.0383 (9)
C11	0.1917 (6)	0.3688 (3)	0.2807 (2)	0.0448 (10)
C12	0.1740 (7)	0.3036 (4)	0.2194 (3)	0.0570 (12)
H12	0.1764	0.3368	0.1736	0.068*
C13	0.1532 (7)	0.1921 (4)	0.2249 (3)	0.0628 (14)
H13	0.1388	0.1487	0.1824	0.075*
C14	0.1526 (7)	0.1407 (4)	0.2903 (3)	0.0568 (12)
H14	0.1393	0.0628	0.2932	0.068*
C15	0.1715 (6)	0.2043 (3)	0.3513 (3)	0.0464 (10)
H15	0.1728	0.1695	0.3968	0.056*
C16	0.3125 (10)	0.9768 (4)	0.5597 (3)	0.0839 (18)
H16A	0.2108	1.0030	0.5869	0.126*
H16B	0.3153	1.0217	0.5163	0.126*
H16C	0.4343	0.9831	0.5893	0.126*
H3O	0.235 (11)	0.509 (6)	0.313 (4)	0.126*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0542 (7)	0.0619 (7)	0.0709 (9)	0.0012 (6)	0.0213 (6)	0.0147 (6)
S1	0.0503 (7)	0.0366 (5)	0.0514 (7)	0.0043 (5)	−0.0005 (5)	0.0050 (5)
O1	0.0359 (17)	0.073 (2)	0.066 (2)	0.0084 (15)	−0.0010 (14)	0.0259 (17)
O2	0.086 (3)	0.0398 (17)	0.066 (2)	−0.0017 (16)	−0.0010 (18)	0.0182 (15)
O3	0.094 (3)	0.0417 (18)	0.054 (2)	0.0080 (17)	0.0063 (19)	0.0097 (15)
N1	0.060 (2)	0.0312 (17)	0.052 (2)	0.0033 (16)	−0.0057 (17)	−0.0064 (15)
N2	0.049 (2)	0.0353 (17)	0.038 (2)	−0.0009 (15)	0.0044 (15)	−0.0005 (14)
N3	0.052 (2)	0.0315 (16)	0.040 (2)	−0.0002 (14)	0.0060 (15)	−0.0033 (14)
C1	0.035 (2)	0.041 (2)	0.041 (2)	0.0017 (17)	−0.0009 (17)	−0.0064 (18)
C2	0.055 (3)	0.062 (3)	0.045 (3)	0.001 (2)	0.001 (2)	−0.016 (2)
C3	0.058 (3)	0.095 (4)	0.034 (3)	−0.005 (3)	0.004 (2)	−0.015 (3)
C4	0.061 (3)	0.075 (3)	0.037 (3)	−0.004 (2)	0.004 (2)	0.011 (2)
C5	0.051 (3)	0.046 (2)	0.042 (3)	−0.0043 (19)	0.0007 (19)	0.0059 (19)
C6	0.032 (2)	0.040 (2)	0.033 (2)	−0.0003 (16)	0.0024 (15)	0.0014 (17)
C7	0.036 (2)	0.0306 (18)	0.035 (2)	0.0025 (15)	0.0018 (16)	0.0031 (16)
C8	0.051 (2)	0.0322 (19)	0.037 (2)	0.0031 (17)	0.0035 (18)	0.0001 (17)
C9	0.042 (2)	0.035 (2)	0.043 (2)	0.0007 (17)	0.0047 (18)	0.0022 (17)
C10	0.037 (2)	0.0342 (19)	0.043 (2)	0.0021 (16)	0.0013 (17)	−0.0020 (17)
C11	0.042 (2)	0.042 (2)	0.050 (3)	0.0069 (18)	−0.0001 (19)	0.0010 (19)
C12	0.061 (3)	0.069 (3)	0.040 (3)	0.007 (2)	0.000 (2)	−0.006 (2)
C13	0.059 (3)	0.063 (3)	0.066 (3)	0.003 (2)	0.004 (2)	−0.026 (3)
C14	0.056 (3)	0.043 (2)	0.072 (3)	−0.005 (2)	0.011 (2)	−0.015 (2)
C15	0.046 (3)	0.035 (2)	0.059 (3)	−0.0032 (18)	0.007 (2)	−0.007 (2)
C16	0.123 (5)	0.040 (3)	0.086 (4)	−0.004 (3)	−0.005 (4)	−0.016 (3)

Geometric parameters (Å, º) top

Cl1—C8	1.786 (4)	C5—C6	1.391 (5)
S1—O2	1.430 (3)	C5—H5	0.9500
S1—O1	1.445 (3)	C6—C7	1.475 (5)
S1—N1	1.623 (4)	C7—C8	1.509 (5)
S1—C8	1.770 (4)	C8—H8	1.0000
O3—C11	1.346 (5)	C9—C10	1.447 (5)
O3—H3O	0.82 (7)	C9—H9	0.9500
N1—C1	1.420 (5)	C10—C11	1.391 (6)
N1—C16	1.479 (6)	C10—C15	1.399 (5)
N2—C7	1.280 (5)	C11—C12	1.388 (6)
N2—N3	1.389 (5)	C12—C13	1.362 (7)
N3—C9	1.286 (5)	C12—H12	0.9500
C1—C6	1.399 (5)	C13—C14	1.374 (7)
C1—C2	1.405 (6)	C13—H13	0.9500
C2—C3	1.355 (7)	C14—C15	1.372 (6)
C2—H2	0.9500	C14—H14	0.9500
C3—C4	1.375 (7)	C15—H15	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.371 (6)	C16—H16B	0.9800
C4—H4	0.9500	C16—H16C	0.9800

O2—S1—O1	119.2 (2)	C7—C8—S1	109.6 (3)
O2—S1—N1	108.3 (2)	C7—C8—Cl1	111.1 (3)
O1—S1—N1	113.8 (2)	S1—C8—Cl1	110.0 (2)
O2—S1—C8	111.0 (2)	C7—C8—H8	108.7
O1—S1—C8	102.2 (2)	S1—C8—H8	108.7
N1—S1—C8	100.35 (19)	Cl1—C8—H8	108.7
C11—O3—H3O	111 (5)	N3—C9—C10	123.1 (4)
C1—N1—C16	120.1 (4)	N3—C9—H9	118.4
C1—N1—S1	118.1 (3)	C10—C9—H9	118.4
C16—N1—S1	119.0 (3)	C11—C10—C15	118.8 (4)
C7—N2—N3	116.8 (3)	C11—C10—C9	123.3 (4)
C9—N3—N2	110.0 (3)	C15—C10—C9	117.9 (4)
C6—C1—C2	119.1 (4)	O3—C11—C12	118.9 (4)
C6—C1—N1	121.5 (3)	O3—C11—C10	121.6 (4)
C2—C1—N1	119.4 (4)	C12—C11—C10	119.5 (4)
C3—C2—C1	120.3 (4)	C13—C12—C11	120.1 (5)
C3—C2—H2	119.8	C13—C12—H12	119.9
C1—C2—H2	119.8	C11—C12—H12	119.9
C2—C3—C4	121.3 (4)	C12—C13—C14	121.7 (5)
C2—C3—H3	119.4	C12—C13—H13	119.2
C4—C3—H3	119.4	C14—C13—H13	119.2
C5—C4—C3	119.1 (4)	C15—C14—C13	118.7 (4)
C5—C4—H4	120.4	C15—C14—H14	120.6
C3—C4—H4	120.4	C13—C14—H14	120.6
C4—C5—C6	121.6 (4)	C14—C15—C10	121.2 (4)
C4—C5—H5	119.2	C14—C15—H15	119.4
C6—C5—H5	119.2	C10—C15—H15	119.4
C5—C6—C1	118.5 (4)	N1—C16—H16A	109.5
C5—C6—C7	118.8 (3)	N1—C16—H16B	109.5
C1—C6—C7	122.7 (3)	H16A—C16—H16B	109.5
N2—C7—C6	118.1 (3)	N1—C16—H16C	109.5
N2—C7—C8	123.4 (3)	H16A—C16—H16C	109.5
C6—C7—C8	118.5 (3)	H16B—C16—H16C	109.5

O2—S1—N1—C1	−169.2 (3)	C5—C6—C7—C8	−170.6 (4)
O1—S1—N1—C1	55.7 (4)	C1—C6—C7—C8	9.6 (6)
C8—S1—N1—C1	−52.7 (3)	N2—C7—C8—S1	142.6 (3)
O2—S1—N1—C16	29.7 (5)	C6—C7—C8—S1	−39.0 (4)
O1—S1—N1—C16	−105.4 (4)	N2—C7—C8—Cl1	−95.6 (4)
C8—S1—N1—C16	146.1 (4)	C6—C7—C8—Cl1	82.8 (4)
C7—N2—N3—C9	178.1 (4)	O2—S1—C8—C7	170.5 (3)
C16—N1—C1—C6	−170.4 (4)	O1—S1—C8—C7	−61.3 (3)
S1—N1—C1—C6	28.6 (5)	N1—S1—C8—C7	56.1 (3)
C16—N1—C1—C2	8.4 (6)	O2—S1—C8—Cl1	48.0 (3)
S1—N1—C1—C2	−152.5 (3)	O1—S1—C8—Cl1	176.2 (2)
C6—C1—C2—C3	0.6 (7)	N1—S1—C8—Cl1	−66.4 (2)
N1—C1—C2—C3	−178.3 (4)	N2—N3—C9—C10	−179.2 (3)
C1—C2—C3—C4	−0.8 (8)	N3—C9—C10—C11	0.5 (6)
C2—C3—C4—C5	0.4 (8)	N3—C9—C10—C15	179.5 (4)
C3—C4—C5—C6	0.1 (7)	C15—C10—C11—O3	−178.6 (4)
C4—C5—C6—C1	−0.3 (6)	C9—C10—C11—O3	0.4 (6)
C4—C5—C6—C7	179.9 (4)	C15—C10—C11—C12	1.0 (6)
C2—C1—C6—C5	−0.1 (6)	C9—C10—C11—C12	−180.0 (4)
N1—C1—C6—C5	178.8 (4)	O3—C11—C12—C13	180.0 (4)
C2—C1—C6—C7	179.7 (4)	C10—C11—C12—C13	0.3 (7)
N1—C1—C6—C7	−1.4 (6)	C11—C12—C13—C14	−1.2 (8)
N3—N2—C7—C6	−177.7 (3)	C12—C13—C14—C15	0.7 (8)
N3—N2—C7—C8	0.7 (6)	C13—C14—C15—C10	0.8 (7)
C5—C6—C7—N2	7.9 (5)	C11—C10—C15—C14	−1.6 (6)
C1—C6—C7—N2	−171.9 (4)	C9—C10—C15—C14	179.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···N3	0.82 (7)	1.98 (7)	2.682 (5)	143 (7)
C9—H9···O1ⁱ	0.95	2.55	3.394 (5)	148

Symmetry code: (i) −x, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClN₃O₃S
M_r	363.81
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	7.0973 (5), 12.0957 (7), 18.7396 (13)
β (°)	96.058 (4)
V (Å³)	1599.75 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.19 × 0.08 × 0.07

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.930, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	15526, 3977, 2200
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.073, 0.211, 1.03
No. of reflections	3977
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.13, −0.38

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), 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
O3—H3O···N3	0.82 (7)	1.98 (7)	2.682 (5)	143 (7)
C9—H9···O1ⁱ	0.95	2.55	3.394 (5)	148.1

Symmetry code: (i) −x, −y+1, −z+1.

Acknowledgements

The authors acknowledge the Higher Education Commission of Pakistan for providing a grant for the project to strengthen the Materials Chemistry Laboratory at GC University Lahore, Pakistan.

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). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011). Asian J. Chem. 23, 2101-2105. CAS Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011a). Acta Cryst. E67, o2038. Web of Science CSD CrossRef IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011b). 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
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o307

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-di­oxo-3,4-di­hydro-1H-2,1-benzo­thia­zin-4-yl­­idene)hydrazinyl­­idene]meth­yl}phenol

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-dioxo-3,4-dihydro-1H-2,1-benzothiazin-4-ylidene)hydrazinylidene]methyl}phenol