(3S,4Z)-3-Chloro-1-methyl-4-[(2E)-(3-methyl-benzyl-idene)hydrazinyl-idene]-3,4-dihydro-1H-2,1-benzothia-zine 2,2-dioxide.

In the title compound, C(17)H(16)ClN(3)O(2)S, the dihedral angle between the benzene rings is 7.75 (13)°. The thia-zine 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 mol-ecules 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 = 361.84

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.088

S = 1.03

4265 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1788 Friedel pairs

Flack parameter: 0.47 (6)

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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811056315/hb6582sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811056315/hb6582Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H16ClN3O2S	F(000) = 752
Mr = 361.84	Dx = 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

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

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(Fo2) + (0.041P)2 + 0.2645P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
4265 reflections	Δρmax = 0.24 e Å−3
219 parameters	Δρmin = −0.26 e Å−3
0 restraints	Absolute structure: Flack (1983), 1788 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.47 (6)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .