3-Chloro-1-methyl-4-[2-(3-phenyl-allyl-idene)hydrazinyl-idene]-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(18)H(16)ClN(3)O(2)S, the dihedral angle between the aromatic rings is 4.81 (2)° and the alkyl chain takes on an extended conformation [N-C-C-C = 179.2 (4)°]. The conformation of the thia-zine ring is an envelope, with the S atom displaced by -0.805 (3) Å from the mean plane of the other five atoms (r.m.s. deviation = 0.046 Å). The Cl atom is an axial conformation and is displaced by 1.761 (4) Å from the thia-zine ring plane. In the crystal, inversion dimers linked by pairs of C-H⋯O inter-actions generate R(2) (2)(20) loops and further C-H⋯O hydrogen bonds link the dimers into (001) sheets. Weak aromatic π-π stacking inter-actions [centroid-centroid separations = 3.870 (3) and 3.883 (3) Å] are also observed.

Related literature

For the synthesis and biological activity of the title compound and related materials, see: Shafiq et al. (2011a ▶). For further synthetic details, see: Shafiq et al. (2011b ▶).

Experimental

Crystal data

C18H16ClN3O2S

M = 373.85

Monoclinic,

a = 7.2262 (5) Å

b = 13.5823 (9) Å

c = 17.9818 (12) Å

β = 97.023 (4)°

V = 1751.6 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.35 mm−1

T = 296 K

0.32 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.895, T max = 0.939

8051 measured reflections

3107 independent reflections

1808 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.201

S = 1.03

3107 reflections

227 parameters

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.36 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 (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812051513/bq2381sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051513/bq2381Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812051513/bq2381Isup3.cml

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

C18H16ClN3O2S	F(000) = 776
Mr = 373.85	Dx = 1.418 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 305 reflections
a = 7.2262 (5) Å	θ = 3.5–24.5°
b = 13.5823 (9) Å	µ = 0.35 mm−1
c = 17.9818 (12) Å	T = 296 K
β = 97.023 (4)°	Rod, yellow
V = 1751.6 (2) Å3	0.32 × 0.20 × 0.18 mm
Z = 4

Bruker APEXII CCD diffractometer	3107 independent reflections
Radiation source: fine-focus sealed tube	1808 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
ω scans	θmax = 25.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
Tmin = 0.895, Tmax = 0.939	k = −13→16
8051 measured reflections	l = −21→18

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.201	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1036P)2 + 0.2998P] where P = (Fo2 + 2Fc2)/3
3107 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.97 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.2953 (5)	0.2779 (3)	0.6118 (2)	0.0406 (11)
C2	0.3170 (6)	0.3399 (4)	0.6745 (3)	0.0526 (12)
H2	0.3146	0.4077	0.6673	0.063*
C3	0.3415 (7)	0.3037 (4)	0.7460 (3)	0.0601 (14)
H3	0.3549	0.3465	0.7867	0.072*
C4	0.3463 (7)	0.2037 (4)	0.7574 (3)	0.0622 (14)
H4	0.3660	0.1791	0.8059	0.075*
C5	0.3225 (7)	0.1399 (4)	0.6983 (3)	0.0584 (13)
H5	0.3231	0.0724	0.7069	0.070*
C6	0.2973 (6)	0.1759 (3)	0.6248 (2)	0.0422 (11)
C7	0.3297 (8)	0.0041 (3)	0.5761 (3)	0.0762 (17)
H7A	0.4520	0.0003	0.6036	0.114*
H7B	0.3302	−0.0271	0.5282	0.114*
H7C	0.2419	−0.0286	0.6036	0.114*
C8	0.2780 (6)	0.2531 (3)	0.4704 (3)	0.0422 (11)
H8	0.2142	0.2856	0.4257	0.051*
C9	0.2729 (5)	0.3201 (3)	0.5368 (2)	0.0381 (10)
C10	0.2243 (6)	0.5395 (3)	0.4480 (3)	0.0507 (12)
H10	0.2233	0.5762	0.4916	0.061*
C11	0.2092 (6)	0.5897 (3)	0.3787 (3)	0.0489 (12)
H11	0.2116	0.5542	0.3345	0.059*
C12	0.1917 (6)	0.6871 (3)	0.3759 (3)	0.0480 (12)
H12	0.1893	0.7181	0.4219	0.058*
C13	0.1756 (6)	0.7522 (3)	0.3107 (3)	0.0450 (11)
C14	0.1646 (7)	0.7194 (4)	0.2366 (3)	0.0563 (13)
H14	0.1665	0.6522	0.2266	0.068*
C15	0.1508 (7)	0.7866 (5)	0.1777 (3)	0.0634 (14)
H15	0.1434	0.7639	0.1287	0.076*
C16	0.1482 (7)	0.8848 (5)	0.1912 (3)	0.0683 (15)
H16	0.1402	0.9291	0.1515	0.082*
C17	0.1573 (7)	0.9191 (4)	0.2634 (3)	0.0638 (14)
H17	0.1536	0.9864	0.2725	0.077*
C18	0.1717 (6)	0.8543 (3)	0.3220 (3)	0.0517 (12)
H18	0.1791	0.8786	0.3706	0.062*
S1	0.15957 (18)	0.14181 (8)	0.48575 (7)	0.0514 (4)
O1	0.1890 (5)	0.0698 (2)	0.42999 (19)	0.0666 (10)
O2	−0.0251 (4)	0.1739 (2)	0.49385 (18)	0.0542 (9)
N1	0.2763 (5)	0.1075 (3)	0.5651 (2)	0.0518 (10)
N2	0.2523 (5)	0.4134 (3)	0.5278 (2)	0.0478 (10)
N3	0.2393 (5)	0.4455 (3)	0.4536 (2)	0.0526 (10)
Cl1	0.51237 (17)	0.22812 (9)	0.45547 (8)	0.0621 (4)

	U11	U22	U33	U12	U13	U23
C1	0.043 (2)	0.041 (3)	0.039 (3)	0.0041 (18)	0.0078 (19)	−0.002 (2)
C2	0.064 (3)	0.050 (3)	0.044 (3)	0.006 (2)	0.007 (2)	−0.006 (3)
C3	0.071 (3)	0.075 (4)	0.034 (3)	0.009 (3)	0.006 (2)	−0.016 (3)
C4	0.066 (3)	0.082 (4)	0.038 (3)	0.007 (3)	0.007 (2)	0.009 (3)
C5	0.071 (3)	0.054 (3)	0.049 (3)	0.006 (2)	0.004 (2)	0.013 (3)
C6	0.049 (3)	0.040 (3)	0.038 (3)	0.0043 (19)	0.006 (2)	0.004 (2)
C7	0.116 (5)	0.035 (3)	0.074 (4)	0.008 (3)	−0.004 (3)	0.004 (3)
C8	0.058 (3)	0.032 (2)	0.037 (3)	0.0042 (18)	0.009 (2)	−0.001 (2)
C9	0.045 (2)	0.028 (2)	0.041 (3)	0.0045 (17)	0.0049 (19)	−0.003 (2)
C10	0.063 (3)	0.038 (3)	0.051 (3)	0.002 (2)	0.006 (2)	0.000 (2)
C11	0.065 (3)	0.036 (3)	0.047 (3)	0.001 (2)	0.010 (2)	0.002 (2)
C12	0.060 (3)	0.038 (3)	0.046 (3)	−0.003 (2)	0.010 (2)	0.000 (2)
C13	0.046 (3)	0.042 (3)	0.046 (3)	−0.0007 (18)	0.003 (2)	0.000 (2)
C14	0.065 (3)	0.049 (3)	0.055 (4)	−0.001 (2)	0.008 (2)	−0.009 (3)
C15	0.061 (3)	0.088 (4)	0.039 (3)	−0.009 (3)	0.001 (2)	0.002 (3)
C16	0.065 (3)	0.080 (4)	0.061 (4)	−0.002 (3)	0.010 (3)	0.024 (3)
C17	0.072 (3)	0.046 (3)	0.073 (4)	−0.003 (2)	0.011 (3)	0.016 (3)
C18	0.065 (3)	0.042 (3)	0.050 (3)	−0.003 (2)	0.013 (2)	0.003 (2)
S1	0.0683 (9)	0.0383 (7)	0.0475 (8)	−0.0027 (5)	0.0070 (6)	−0.0040 (6)
O1	0.109 (3)	0.0401 (19)	0.052 (2)	−0.0042 (17)	0.0127 (19)	−0.0149 (17)
O2	0.0472 (19)	0.060 (2)	0.055 (2)	−0.0051 (14)	0.0033 (15)	−0.0113 (17)
N1	0.081 (3)	0.031 (2)	0.042 (3)	0.0058 (17)	0.0017 (19)	0.0016 (19)
N2	0.066 (3)	0.038 (2)	0.039 (2)	0.0037 (16)	0.0049 (18)	0.0004 (18)
N3	0.076 (3)	0.035 (2)	0.046 (3)	0.0026 (18)	0.0063 (19)	0.0018 (19)
Cl1	0.0630 (8)	0.0605 (8)	0.0664 (10)	0.0036 (5)	0.0223 (6)	−0.0108 (7)

C1—C2	1.401 (6)	C10—C11	1.414 (6)
C1—C6	1.405 (6)	C10—H10	0.9300
C1—C9	1.455 (6)	C11—C12	1.329 (6)
C2—C3	1.368 (7)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.462 (6)
C3—C4	1.373 (7)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.398 (7)
C4—C5	1.365 (7)	C13—C18	1.402 (6)
C4—H4	0.9300	C14—C15	1.393 (7)
C5—C6	1.399 (6)	C14—H14	0.9300
C5—H5	0.9300	C15—C16	1.357 (7)
C6—N1	1.415 (6)	C15—H15	0.9300
C7—N1	1.463 (6)	C16—C17	1.373 (7)
C7—H7A	0.9600	C16—H16	0.9300
C7—H7B	0.9600	C17—C18	1.366 (6)
C7—H7C	0.9600	C17—H17	0.9300
C8—C9	1.506 (6)	C18—H18	0.9300
C8—S1	1.775 (4)	S1—O2	1.428 (3)
C8—Cl1	1.780 (4)	S1—O1	1.435 (3)
C8—H8	0.9800	S1—N1	1.634 (4)
C9—N2	1.283 (5)	N2—N3	1.397 (5)
C10—N3	1.284 (5)
C2—C1—C6	117.4 (4)	C12—C11—C10	120.7 (5)
C2—C1—C9	119.8 (4)	C12—C11—H11	119.7
C6—C1—C9	122.8 (4)	C10—C11—H11	119.7
C3—C2—C1	122.0 (5)	C11—C12—C13	129.1 (5)
C3—C2—H2	119.0	C11—C12—H12	115.4
C1—C2—H2	119.0	C13—C12—H12	115.4
C2—C3—C4	119.5 (5)	C14—C13—C18	117.0 (4)
C2—C3—H3	120.2	C14—C13—C12	124.0 (4)
C4—C3—H3	120.2	C18—C13—C12	119.0 (4)
C5—C4—C3	120.9 (5)	C15—C14—C13	120.4 (5)
C5—C4—H4	119.5	C15—C14—H14	119.8
C3—C4—H4	119.5	C13—C14—H14	119.8
C4—C5—C6	120.2 (5)	C16—C15—C14	120.7 (5)
C4—C5—H5	119.9	C16—C15—H15	119.7
C6—C5—H5	119.9	C14—C15—H15	119.7
C5—C6—C1	120.0 (4)	C15—C16—C17	120.2 (5)
C5—C6—N1	118.5 (4)	C15—C16—H16	119.9
C1—C6—N1	121.5 (4)	C17—C16—H16	119.9
N1—C7—H7A	109.5	C18—C17—C16	120.0 (5)
N1—C7—H7B	109.5	C18—C17—H17	120.0
H7A—C7—H7B	109.5	C16—C17—H17	120.0
N1—C7—H7C	109.5	C17—C18—C13	121.8 (5)
H7A—C7—H7C	109.5	C17—C18—H18	119.1
H7B—C7—H7C	109.5	C13—C18—H18	119.1
C9—C8—S1	109.4 (3)	O2—S1—O1	120.0 (2)
C9—C8—Cl1	110.5 (3)	O2—S1—N1	112.8 (2)
S1—C8—Cl1	110.3 (2)	O1—S1—N1	108.1 (2)
C9—C8—H8	108.9	O2—S1—C8	103.3 (2)
S1—C8—H8	108.9	O1—S1—C8	110.9 (2)
Cl1—C8—H8	108.9	N1—S1—C8	99.9 (2)
N2—C9—C1	120.3 (4)	C6—N1—C7	121.7 (4)
N2—C9—C8	120.7 (4)	C6—N1—S1	118.1 (3)
C1—C9—C8	119.1 (4)	C7—N1—S1	119.4 (3)
N3—C10—C11	123.1 (5)	C9—N2—N3	115.0 (4)
N3—C10—H10	118.5	C10—N3—N2	112.4 (4)
C11—C10—H10	118.5
C6—C1—C2—C3	0.8 (6)	C14—C15—C16—C17	−0.7 (8)
C9—C1—C2—C3	−178.9 (4)	C15—C16—C17—C18	0.9 (8)
C1—C2—C3—C4	0.4 (7)	C16—C17—C18—C13	−0.7 (7)
C2—C3—C4—C5	−1.5 (7)	C14—C13—C18—C17	0.2 (7)
C3—C4—C5—C6	1.5 (7)	C12—C13—C18—C17	179.9 (4)
C4—C5—C6—C1	−0.4 (7)	C9—C8—S1—O2	60.3 (3)
C4—C5—C6—N1	178.9 (4)	Cl1—C8—S1—O2	−178.0 (2)
C2—C1—C6—C5	−0.8 (6)	C9—C8—S1—O1	−170.0 (3)
C9—C1—C6—C5	178.9 (4)	Cl1—C8—S1—O1	−48.2 (3)
C2—C1—C6—N1	180.0 (4)	C9—C8—S1—N1	−56.2 (3)
C9—C1—C6—N1	−0.4 (6)	Cl1—C8—S1—N1	65.6 (3)
C2—C1—C9—N2	−7.8 (6)	C5—C6—N1—C7	−16.9 (6)
C6—C1—C9—N2	172.6 (4)	C1—C6—N1—C7	162.4 (4)
C2—C1—C9—C8	171.1 (4)	C5—C6—N1—S1	153.4 (3)
C6—C1—C9—C8	−8.5 (6)	C1—C6—N1—S1	−27.4 (5)
S1—C8—C9—N2	−142.1 (3)	O2—S1—N1—C6	−56.8 (4)
Cl1—C8—C9—N2	96.3 (4)	O1—S1—N1—C6	168.2 (3)
S1—C8—C9—C1	39.1 (5)	C8—S1—N1—C6	52.3 (4)
Cl1—C8—C9—C1	−82.5 (4)	O2—S1—N1—C7	113.7 (4)
N3—C10—C11—C12	179.2 (4)	O1—S1—N1—C7	−21.3 (4)
C10—C11—C12—C13	179.5 (4)	C8—S1—N1—C7	−137.2 (4)
C11—C12—C13—C14	4.2 (7)	C1—C9—N2—N3	177.7 (3)
C11—C12—C13—C18	−175.5 (5)	C8—C9—N2—N3	−1.2 (5)
C18—C13—C14—C15	0.1 (7)	C11—C10—N3—N2	180.0 (4)
C12—C13—C14—C15	−179.5 (4)	C9—N2—N3—C10	−178.1 (4)
C13—C14—C15—C16	0.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2i	0.93	2.51	3.345 (6)	150
C15—H15···O2ii	0.93	2.57	3.464 (6)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2i	0.93	2.51	3.345 (6)	150
C15—H15⋯O2ii	0.93	2.57	3.464 (6)	161

Symmetry codes: (i) ; (ii) .