2-{(E)-[(2Z)-(3-Chloro-1-methyl-2,2-di-oxo-3,4-dihydro-1H-2,1-benzo-thia-zin-4-yl-idene)hydrazinyl-idene]meth-yl}phenol.

In the title compound, C(16)H(14)ClN(3)O(3)S, the thia-zine 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 thia-zine mean plane [-0.3976 (12) and 0.3179 (14) Å, respectively]. The conformations around the double bonds in the R(2)C=N-N=CHR unit are Z and E. An intra-molecular O-H⋯N hydrogen bond with the hy-droxy group as donor generates an S(6) ring motif. In the crystal, pairs of weak C-H⋯O inter-actions connect the mol-ecules, 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 = 363.81

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.211

S = 1.03

3977 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.13 e Å−3

Δρmin = −0.38 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055978/bh2407sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811055978/bh2407Isup3.cml

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

C16H14ClN3O3S	F(000) = 752
Mr = 363.81	Dx = 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

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

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(Fo2) + (0.0873P)2 + 1.6824P] where P = (Fo2 + 2Fc2)/3
3977 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 1.13 e Å−3
0 restraints	Δρmin = −0.38 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .