(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methyl­benzyl­idene)hydrazinyl­idene]-3,4-dihydro-1H-2,1-benzothia­zine 2,2-dioxide

Shafiq, M.; Tahir, M.N.; Khan, I.U.; Zia-Ur-Rehman, M.

doi:10.1107/S1600536811056315

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o338

doi:10.1107/S1600536811056315

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(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methylbenzylidene)hydrazinylidene]-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide

Muhammad Shafiq,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan ^a and Muhammad Zia-Ur-Rehman ^c

^aMaterials Chemistry Laboratory, Department of Chemistry, Government College University, Lahore, Pakistan, ^bUniversity of Sargodha, Department of Physics, Sargodha, Pakistan, and ^cApplied Chemistry Research Center, PCSIR Laboratories Complex, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 28 December 2011; accepted 31 December 2011; online 11 January 2012)

In the title compound, C₁₇H₁₆ClN₃O₂S, the dihedral angle between the benzene rings is 7.75 (13)°. The thiazine ring adopts an envelope conformation with the S atom as the flap at a distance of 0.813 (2) Å from the plane through the other five atoms. In the crystal, C—H⋯O hydrogen bonds link the molecules into chains propagating in [100].

Related literature

For related structures, see: Shafiq et al. (2011a ,b ,c ). For further synthetic details, see: Shafiq et al. (2011d ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₇H₁₆ClN₃O₂S
M_r = 361.84
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7734 (2) Å
b = 11.1271 (2) Å
c = 17.9423 (3) Å
V = 1751.57 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.26 × 0.18 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.930, T_max = 0.960
17152 measured reflections
4265 independent reflections
3478 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.088
S = 1.03
4265 reflections
219 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Absolute structure: Flack (1983 ), 1788 Friedel pairs
Flack parameter: 0.47 (6)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O2ⁱ	0.93	2.57	3.469 (3)	163
C10—H10⋯O1ⁱⁱ	0.93	2.53	3.300 (3)	140
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y, z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); 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 global, I. DOI: 10.1107/S1600536811056315/hb6582sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811056315/hb6582Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811056315/hb6582Isup3.cml

checkCIF report

Comment top

The title compound (I), (Fig. 1) has been synthesized in continuation of our studies of Schiff bases (Shafiq et al., 2011a,b,c).

In (I), the benzene rings A (C1—C6) and B (C11—C16) are planar with r. m. s. deviation of 0.0033 and 0.0002 Å, respectively. The dihedral angle between A/B is 7.75 (13)°. The central group C (N2/N3/C10) is of course planar. The dihedral angle between A/C and B/C is 6.02 (19) and 5.11 (21)°, respectively. The thiazine ring D (C1/C6/C9/C8/S1/N1) is in the nvelope form, with the maximum puckering amplitude (Cremer & Pople, 1975), Q = 0.5707 (16) Å. The molecules form one-dimensional polymeric chains extending along the a-axis due to H-bonding of C—H···O type (Table 1).

Related literature top

For related structures, see: Shafiq et al. (2011a,b,c). For further synthetic details, see: Shafiq et al. (2011d). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

Schiff base derivative of (4Z)-4-hydrazinylidene-1-methyl-3,4-dihydro -1H-2,1-benzothiazine 2,2-dioxide and 3-methylbenzaldehyde was prepared using the method reported previously (Shafiq et al. 2011d). The chlorination of the schiff base was undertaken using N-chloro succinimide and dibenzoylperoxide (Shafiq et al., 2011a). The crude product was re-crystallized from ethyl acetate to yield orange needles of (I).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. View of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. The partial packing showing chains extending along the [100] direction.

(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3- methylbenzylidene)hydrazinylidene]-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide top

Crystal data top

C₁₇H₁₆ClN₃O₂S	F(000) = 752
M_r = 361.84	D_x = 1.372 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2106 reflections
a = 8.7734 (2) Å	θ = 1.4–25.3°
b = 11.1271 (2) Å	µ = 0.35 mm⁻¹
c = 17.9423 (3) Å	T = 296 K
V = 1751.57 (6) Å³	Needle, orange
Z = 4	0.26 × 0.18 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4265 independent reflections
Radiation source: fine-focus sealed tube	3478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 7.50 pixels mm^-1	θ_max = 28.3°, θ_min = 2.2°
ω scans	h = −10→11
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→14
T_min = 0.930, T_max = 0.960	l = −23→23
17152 measured reflections

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)] = 0.036	H-atom parameters constrained
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.041P)² + 0.2645P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4265 reflections	Δρ_max = 0.24 e Å⁻³
219 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1788 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.47 (6)

Crystal data top

C₁₇H₁₆ClN₃O₂S	V = 1751.57 (6) Å³
M_r = 361.84	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7734 (2) Å	µ = 0.35 mm⁻¹
b = 11.1271 (2) Å	T = 296 K
c = 17.9423 (3) Å	0.26 × 0.18 × 0.12 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4265 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3478 reflections with I > 2σ(I)
T_min = 0.930, T_max = 0.960	R_int = 0.029
17152 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.24 e Å⁻³
S = 1.03	Δρ_min = −0.27 e Å⁻³
4265 reflections	Absolute structure: Flack (1983), 1788 Friedel pairs
219 parameters	Absolute structure parameter: 0.47 (6)
0 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
Cl1	0.16886 (7)	0.16151 (6)	0.00310 (3)	0.0619 (2)
S1	0.10071 (6)	0.09643 (5)	0.15565 (3)	0.0411 (2)
O1	−0.04053 (18)	0.05118 (15)	0.12847 (9)	0.0559 (6)
O2	0.17040 (19)	0.04041 (14)	0.21814 (8)	0.0524 (5)
N1	0.0827 (2)	0.23974 (17)	0.16940 (11)	0.0453 (6)
N2	0.5175 (2)	0.13115 (15)	0.09335 (10)	0.0410 (5)
N3	0.5229 (2)	0.03374 (16)	0.04310 (10)	0.0467 (6)
C1	0.2182 (3)	0.30519 (17)	0.18673 (11)	0.0381 (6)
C2	0.2065 (3)	0.4082 (2)	0.22991 (13)	0.0523 (8)
C3	0.3334 (3)	0.4739 (2)	0.24869 (13)	0.0531 (8)
C4	0.4751 (3)	0.4373 (2)	0.22482 (12)	0.0499 (8)
C5	0.4885 (3)	0.3360 (2)	0.18144 (11)	0.0422 (7)
C6	0.3614 (2)	0.26764 (17)	0.16138 (10)	0.0338 (6)
C7	−0.0609 (3)	0.3020 (3)	0.15644 (19)	0.0690 (10)
C8	0.2429 (2)	0.09333 (19)	0.08520 (10)	0.0380 (6)
C9	0.3815 (2)	0.16115 (17)	0.11258 (10)	0.0339 (6)
C10	0.6581 (3)	0.01494 (19)	0.02078 (12)	0.0455 (7)
C11	0.6974 (3)	−0.07862 (19)	−0.03287 (12)	0.0464 (7)
C12	0.5872 (3)	−0.1500 (3)	−0.06694 (14)	0.0668 (10)
C13	0.6332 (4)	−0.2383 (3)	−0.11655 (18)	0.0808 (13)
C14	0.7839 (4)	−0.2554 (2)	−0.13190 (16)	0.0751 (12)
C15	0.8968 (3)	−0.1863 (2)	−0.09916 (14)	0.0588 (8)
C16	0.8497 (3)	−0.0975 (2)	−0.04930 (12)	0.0513 (8)
C17	1.0632 (4)	−0.2042 (3)	−0.11637 (18)	0.0803 (11)
H2	0.11120	0.43326	0.24642	0.0628*
H3	0.32356	0.54297	0.27748	0.0637*
H4	0.56141	0.48092	0.23799	0.0598*
H5	0.58447	0.31247	0.16504	0.0506*
H7A	−0.10558	0.32386	0.20337	0.1034*
H7B	−0.12931	0.25007	0.12985	0.1034*
H7C	−0.04256	0.37318	0.12755	0.1034*
H8	0.27104	0.00984	0.07453	0.0456*
H10	0.73577	0.06310	0.03951	0.0545*
H12	0.48435	−0.13858	−0.05656	0.0802*
H13	0.56053	−0.28641	−0.13963	0.0969*
H14	0.81172	−0.31540	−0.16535	0.0899*
H16	0.92277	−0.04956	−0.02640	0.0616*
H17A	1.09454	−0.28229	−0.09956	0.1203*
H17B	1.12213	−0.14373	−0.09134	0.1203*
H17C	1.07907	−0.19801	−0.16917	0.1203*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0545 (4)	0.0921 (4)	0.0390 (3)	−0.0107 (3)	−0.0091 (3)	0.0114 (3)
S1	0.0304 (3)	0.0494 (3)	0.0434 (3)	−0.0036 (2)	0.0022 (2)	0.0065 (2)
O1	0.0360 (10)	0.0662 (10)	0.0655 (10)	−0.0139 (8)	−0.0005 (8)	0.0038 (8)
O2	0.0459 (10)	0.0616 (9)	0.0497 (8)	−0.0011 (8)	0.0023 (8)	0.0190 (7)
N1	0.0253 (10)	0.0544 (10)	0.0561 (11)	0.0053 (8)	0.0001 (8)	−0.0009 (8)
N2	0.0357 (10)	0.0437 (9)	0.0435 (9)	0.0038 (8)	0.0036 (8)	−0.0065 (7)
N3	0.0414 (12)	0.0459 (10)	0.0527 (10)	−0.0009 (9)	0.0088 (9)	−0.0098 (8)
C1	0.0322 (11)	0.0447 (11)	0.0374 (10)	0.0049 (9)	−0.0006 (8)	−0.0003 (8)
C2	0.0417 (13)	0.0592 (13)	0.0561 (13)	0.0133 (12)	0.0043 (11)	−0.0130 (12)
C3	0.0569 (17)	0.0487 (12)	0.0537 (12)	0.0045 (12)	−0.0028 (12)	−0.0115 (10)
C4	0.0488 (15)	0.0507 (12)	0.0501 (12)	−0.0065 (11)	−0.0107 (11)	−0.0038 (10)
C5	0.0331 (12)	0.0520 (12)	0.0414 (10)	−0.0031 (10)	0.0002 (9)	−0.0009 (9)
C6	0.0301 (11)	0.0399 (9)	0.0315 (9)	0.0022 (8)	−0.0007 (8)	0.0017 (8)
C7	0.0372 (15)	0.0779 (19)	0.092 (2)	0.0183 (12)	−0.0136 (14)	−0.0157 (17)
C8	0.0340 (11)	0.0412 (10)	0.0389 (10)	−0.0015 (9)	0.0017 (9)	0.0008 (9)
C9	0.0285 (11)	0.0386 (9)	0.0347 (9)	0.0022 (9)	0.0005 (8)	0.0035 (8)
C10	0.0416 (13)	0.0473 (12)	0.0475 (11)	0.0076 (10)	0.0017 (10)	−0.0071 (9)
C11	0.0489 (14)	0.0422 (11)	0.0481 (11)	0.0029 (11)	0.0066 (10)	−0.0052 (9)
C12	0.0661 (18)	0.0677 (16)	0.0667 (16)	−0.0120 (15)	0.0121 (14)	−0.0195 (14)
C13	0.093 (3)	0.0663 (17)	0.083 (2)	−0.0196 (17)	0.0097 (18)	−0.0307 (15)
C14	0.110 (3)	0.0500 (14)	0.0652 (16)	0.0004 (17)	0.0260 (17)	−0.0173 (12)
C15	0.0755 (18)	0.0493 (13)	0.0516 (12)	0.0193 (14)	0.0202 (14)	0.0017 (10)
C16	0.0553 (15)	0.0465 (12)	0.0521 (12)	0.0091 (12)	0.0076 (11)	−0.0046 (10)
C17	0.084 (2)	0.080 (2)	0.0770 (19)	0.0358 (17)	0.0277 (17)	0.0024 (16)

Geometric parameters (Å, º) top

Cl1—C8	1.7797 (19)	C12—C13	1.386 (4)
S1—O1	1.4237 (17)	C13—C14	1.364 (5)
S1—O2	1.4211 (16)	C14—C15	1.385 (4)
S1—N1	1.621 (2)	C15—C16	1.396 (3)
S1—C8	1.7763 (19)	C15—C17	1.505 (4)
N1—C1	1.428 (3)	C2—H2	0.9300
N1—C7	1.457 (3)	C3—H3	0.9300
N2—N3	1.411 (2)	C4—H4	0.9300
N2—C9	1.286 (2)	C5—H5	0.9300
N3—C10	1.269 (3)	C7—H7A	0.9600
C1—C2	1.387 (3)	C7—H7B	0.9600
C1—C6	1.400 (3)	C7—H7C	0.9600
C2—C3	1.374 (4)	C8—H8	0.9800
C3—C4	1.377 (4)	C10—H10	0.9300
C4—C5	1.375 (3)	C12—H12	0.9300
C5—C6	1.397 (3)	C13—H13	0.9300
C6—C9	1.484 (3)	C14—H14	0.9300
C8—C9	1.513 (3)	C16—H16	0.9300
C10—C11	1.459 (3)	C17—H17A	0.9600
C11—C12	1.393 (4)	C17—H17B	0.9600
C11—C16	1.384 (4)	C17—H17C	0.9600

O1—S1—O2	119.32 (10)	C16—C15—C17	120.8 (2)
O1—S1—N1	108.37 (10)	C11—C16—C15	122.0 (2)
O1—S1—C8	111.14 (9)	C1—C2—H2	119.00
O2—S1—N1	110.69 (10)	C3—C2—H2	119.00
O2—S1—C8	104.52 (9)	C2—C3—H3	120.00
N1—S1—C8	101.29 (10)	C4—C3—H3	120.00
S1—N1—C1	116.97 (14)	C3—C4—H4	120.00
S1—N1—C7	121.86 (17)	C5—C4—H4	120.00
C1—N1—C7	120.8 (2)	C4—C5—H5	119.00
N3—N2—C9	113.71 (16)	C6—C5—H5	119.00
N2—N3—C10	111.08 (17)	N1—C7—H7A	109.00
N1—C1—C2	118.8 (2)	N1—C7—H7B	110.00
N1—C1—C6	121.60 (17)	N1—C7—H7C	109.00
C2—C1—C6	119.6 (2)	H7A—C7—H7B	109.00
C1—C2—C3	121.1 (2)	H7A—C7—H7C	109.00
C2—C3—C4	119.9 (2)	H7B—C7—H7C	109.00
C3—C4—C5	119.7 (2)	Cl1—C8—H8	110.00
C4—C5—C6	121.6 (2)	S1—C8—H8	110.00
C1—C6—C5	118.04 (18)	C9—C8—H8	109.00
C1—C6—C9	122.46 (17)	N3—C10—H10	118.00
C5—C6—C9	119.47 (17)	C11—C10—H10	118.00
Cl1—C8—S1	108.93 (10)	C11—C12—H12	121.00
Cl1—C8—C9	110.45 (14)	C13—C12—H12	121.00
S1—C8—C9	108.89 (13)	C12—C13—H13	120.00
N2—C9—C6	118.41 (16)	C14—C13—H13	120.00
N2—C9—C8	121.94 (17)	C13—C14—H14	119.00
C6—C9—C8	119.63 (15)	C15—C14—H14	119.00
N3—C10—C11	123.1 (2)	C11—C16—H16	119.00
C10—C11—C12	122.2 (2)	C15—C16—H16	119.00
C10—C11—C16	118.5 (2)	C15—C17—H17A	109.00
C12—C11—C16	119.4 (2)	C15—C17—H17B	109.00
C11—C12—C13	119.0 (3)	C15—C17—H17C	109.00
C12—C13—C14	120.7 (3)	H17A—C17—H17B	109.00
C13—C14—C15	122.0 (3)	H17A—C17—H17C	109.00
C14—C15—C16	117.0 (2)	H17B—C17—H17C	109.00
C14—C15—C17	122.2 (2)

O1—S1—N1—C1	−171.41 (15)	C1—C2—C3—C4	−0.3 (3)
O1—S1—N1—C7	1.7 (2)	C2—C3—C4—C5	0.9 (3)
O2—S1—N1—C1	55.99 (18)	C3—C4—C5—C6	−0.8 (3)
O2—S1—N1—C7	−130.9 (2)	C4—C5—C6—C1	0.1 (3)
C8—S1—N1—C1	−54.42 (17)	C4—C5—C6—C9	178.17 (19)
C8—S1—N1—C7	118.7 (2)	C1—C6—C9—N2	−178.30 (18)
O1—S1—C8—Cl1	49.97 (14)	C1—C6—C9—C8	3.4 (3)
O1—S1—C8—C9	170.49 (13)	C5—C6—C9—N2	3.7 (3)
O2—S1—C8—Cl1	179.94 (12)	C5—C6—C9—C8	−174.64 (17)
O2—S1—C8—C9	−59.54 (15)	Cl1—C8—C9—N2	−93.1 (2)
N1—S1—C8—Cl1	−64.97 (12)	Cl1—C8—C9—C6	85.20 (18)
N1—S1—C8—C9	55.54 (15)	S1—C8—C9—N2	147.38 (16)
S1—N1—C1—C2	−151.50 (17)	S1—C8—C9—C6	−34.4 (2)
S1—N1—C1—C6	28.4 (3)	N3—C10—C11—C12	3.8 (4)
C7—N1—C1—C2	35.3 (3)	N3—C10—C11—C16	−175.3 (2)
C7—N1—C1—C6	−144.8 (2)	C10—C11—C12—C13	−179.1 (2)
C9—N2—N3—C10	174.07 (18)	C16—C11—C12—C13	0.0 (4)
N3—N2—C9—C6	−176.04 (16)	C10—C11—C16—C15	179.1 (2)
N3—N2—C9—C8	2.2 (3)	C12—C11—C16—C15	0.0 (3)
N2—N3—C10—C11	−178.60 (19)	C11—C12—C13—C14	0.0 (4)
N1—C1—C2—C3	179.5 (2)	C12—C13—C14—C15	0.0 (5)
C6—C1—C2—C3	−0.4 (3)	C13—C14—C15—C16	0.0 (4)
N1—C1—C6—C5	−179.34 (18)	C13—C14—C15—C17	−179.5 (3)
N1—C1—C6—C9	2.6 (3)	C14—C15—C16—C11	0.0 (3)
C2—C1—C6—C5	0.5 (3)	C17—C15—C16—C11	179.6 (2)
C2—C1—C6—C9	−177.55 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O2ⁱ	0.93	2.57	3.469 (3)	163
C10—H10···O1ⁱⁱ	0.93	2.53	3.300 (3)	140

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

Experimental details

Crystal data
Chemical formula	C₁₇H₁₆ClN₃O₂S
M_r	361.84
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.7734 (2), 11.1271 (2), 17.9423 (3)
V (Å³)	1751.57 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.35
Crystal size (mm)	0.26 × 0.18 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.930, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	17152, 4265, 3478
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.088, 1.03
No. of reflections	4265
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.27
Absolute structure	Flack (1983), 1788 Friedel pairs
Absolute structure parameter	0.47 (6)

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
C4—H4···O2ⁱ	0.93	2.57	3.469 (3)	163
C10—H10···O1ⁱⁱ	0.93	2.53	3.300 (3)	140

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

Acknowledgements

MS gratefully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing a scholarship under the Indigenous PhD Program (PIN 042–120567-PS2–276).

References

Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science 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
Flack, H. D. (1983). Acta Cryst. A39, 876-881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Shafiq, M., Khan, I. U., Arshad, M. N. & Siddiqui, W. A. (2011a). Asian J. Chem. 23, 2101–2106. CAS Google Scholar
Shafiq, M., Khan, I. U., Zia-ur-Rehman, M., Arshad, M. N. & Asiri, A. M. (2011b). 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. (2011c). 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. (2011d). J. Chil. Chem. Soc. 56, 527–531. 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 o338

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

(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methyl­benzyl­­idene)hydrazinyl­­idene]-3,4-di­hydro-1H-2,1-benzo­thia­zine 2,2-dioxide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methylbenzylidene)hydrazinylidene]-3,4-dihydro-1H-2,1-benzothiazine 2,2-dioxide