1-Methyl-4-[1-(1-phenyl-ethyl-idene)-hydrazin-2-yl-idene]-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(17)H(17)N(3)O(2)S, the phenyl ring is oriented at dihedral angles of 8.5 (2) and 1.17 (14)°, respectively, to the C=N-N plane and the fused aromatic ring. The thia-zine ring adopts an envelope conformation with the S atom at the flap. In the crystal, a weak C-H⋯O inter-action connects the mol-ecules, forming a helical chain along the a axis.

Related literature

For the synthesis, see: Shafiq et al. (2011 ▶). For related structures, see: Shafiq et al. (2011a ▶,b ▶, 2012 ▶).

Experimental

Crystal data

C17H17N3O2S

M = 327.40

Orthorhombic,

a = 6.6678 (2) Å

b = 12.0783 (6) Å

c = 20.0529 (8) Å

V = 1614.97 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.21 mm−1

T = 296 K

0.38 × 0.11 × 0.07 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.923, T max = 0.985

9111 measured reflections

3830 independent reflections

2819 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.108

S = 0.97

3828 reflections

210 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.27 e Å−3

Absolute structure: Flack (1983 ▶), 1577 Friedel pairs

Flack parameter: −0.06 (9)

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: PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536812025743/is5153sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025743/is5153Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812025743/is5153Isup3.cml

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

C17H17N3O2S	F(000) = 688
Mr = 327.40	Dx = 1.347 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2415 reflections
a = 6.6678 (2) Å	θ = 2.6–21.1°
b = 12.0783 (6) Å	µ = 0.21 mm−1
c = 20.0529 (8) Å	T = 296 K
V = 1614.97 (11) Å3	Needle, colorless
Z = 4	0.38 × 0.11 × 0.07 mm

Bruker Kappa APEXII CCD diffractometer	3830 independent reflections
Radiation source: fine-focus sealed tube	2819 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→6
Tmin = 0.923, Tmax = 0.985	k = −16→13
9111 measured reflections	l = −26→18

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0554P)2 + 0.0282P] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max = 0.007
3828 reflections	Δρmax = 0.21 e Å−3
210 parameters	Δρmin = −0.27 e Å−3
0 restraints	Absolute structure: Flack (1983), 1577 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.06 (9)

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	−0.0436 (3)	0.1646 (2)	0.19872 (12)	0.0434 (6)
C2	−0.1882 (4)	0.1755 (3)	0.24813 (14)	0.0607 (8)
H2	−0.2979	0.2216	0.2412	0.073*
C3	−0.1708 (5)	0.1190 (3)	0.30686 (14)	0.0689 (9)
H3	−0.2704	0.1259	0.3390	0.083*
C4	−0.0087 (5)	0.0522 (3)	0.31910 (14)	0.0703 (9)
H4	0.0036	0.0154	0.3596	0.084*
C5	0.1365 (5)	0.0404 (2)	0.27030 (12)	0.0592 (7)
H5	0.2473	−0.0044	0.2785	0.071*
C6	0.1196 (4)	0.09462 (19)	0.20875 (11)	0.0425 (5)
C7	0.2735 (3)	0.07398 (19)	0.15723 (11)	0.0401 (5)
C8	0.2426 (3)	0.12341 (18)	0.08901 (11)	0.0394 (5)
H8A	0.1559	0.0756	0.0629	0.047*
H8B	0.3705	0.1291	0.0662	0.047*
C9	0.6894 (3)	−0.07684 (19)	0.12801 (12)	0.0448 (6)
C10	0.8400 (3)	−0.08935 (19)	0.07412 (12)	0.0446 (6)
C11	0.8205 (4)	−0.0311 (2)	0.01409 (12)	0.0485 (6)
H11	0.7109	0.0153	0.0078	0.058*
C12	0.9605 (4)	−0.0414 (2)	−0.03551 (13)	0.0573 (7)
H12	0.9457	−0.0014	−0.0748	0.069*
C13	1.1223 (4)	−0.1103 (3)	−0.02763 (15)	0.0666 (8)
H13	1.2158	−0.1178	−0.0617	0.080*
C14	1.1456 (4)	−0.1680 (3)	0.03080 (16)	0.0723 (8)
H14	1.2560	−0.2141	0.0365	0.087*
C15	1.0061 (4)	−0.1578 (2)	0.08111 (15)	0.0571 (7)
H15	1.0234	−0.1975	0.1204	0.068*
C16	0.6984 (5)	−0.1505 (3)	0.18763 (15)	0.0859 (11)
H16A	0.6132	−0.1214	0.2220	0.129*
H16B	0.8339	−0.1541	0.2037	0.129*
H16C	0.6538	−0.2234	0.1756	0.129*
C17	−0.2573 (3)	0.2746 (2)	0.12031 (13)	0.0601 (8)
H17A	−0.3647	0.2230	0.1275	0.090*
H17B	−0.2542	0.2957	0.0742	0.090*
H17C	−0.2782	0.3391	0.1474	0.090*
N1	−0.0679 (3)	0.22309 (19)	0.13822 (10)	0.0543 (6)
N2	0.4234 (3)	0.01227 (18)	0.17172 (10)	0.0500 (5)
N3	0.5596 (3)	−0.00040 (18)	0.11964 (10)	0.0508 (5)
O1	0.0707 (2)	0.29407 (17)	0.03230 (9)	0.0663 (6)
O2	0.2661 (2)	0.32168 (14)	0.13476 (9)	0.0559 (5)
S1	0.13459 (7)	0.25435 (5)	0.09576 (3)	0.04299 (16)

	U11	U22	U33	U12	U13	U23
C1	0.0355 (12)	0.0530 (15)	0.0417 (13)	−0.0110 (11)	0.0034 (10)	−0.0029 (11)
C2	0.0496 (15)	0.073 (2)	0.0592 (17)	−0.0102 (14)	0.0168 (12)	−0.0038 (15)
C3	0.072 (2)	0.080 (2)	0.0548 (18)	−0.0237 (17)	0.0264 (15)	−0.0051 (16)
C4	0.103 (2)	0.063 (2)	0.0452 (16)	−0.0274 (18)	0.0170 (17)	0.0015 (14)
C5	0.0776 (17)	0.0510 (16)	0.0489 (16)	−0.0075 (15)	0.0031 (15)	0.0062 (12)
C6	0.0466 (13)	0.0416 (13)	0.0392 (12)	−0.0097 (11)	0.0021 (11)	−0.0003 (10)
C7	0.0427 (12)	0.0382 (12)	0.0395 (13)	−0.0067 (10)	0.0019 (10)	0.0023 (10)
C8	0.0385 (12)	0.0417 (12)	0.0380 (12)	−0.0005 (9)	0.0027 (10)	0.0002 (11)
C9	0.0459 (13)	0.0354 (13)	0.0531 (14)	−0.0007 (10)	−0.0081 (11)	0.0037 (11)
C10	0.0443 (13)	0.0360 (12)	0.0536 (14)	−0.0027 (10)	−0.0086 (11)	−0.0010 (10)
C11	0.0454 (13)	0.0447 (15)	0.0555 (16)	0.0030 (11)	−0.0077 (11)	0.0006 (12)
C12	0.0661 (17)	0.0553 (17)	0.0506 (16)	−0.0018 (14)	−0.0047 (14)	−0.0050 (13)
C13	0.0637 (17)	0.067 (2)	0.0694 (19)	0.0017 (16)	0.0120 (16)	−0.0144 (17)
C14	0.0625 (17)	0.064 (2)	0.090 (2)	0.0226 (16)	0.0003 (18)	−0.0040 (17)
C15	0.0568 (15)	0.0448 (15)	0.0695 (18)	0.0119 (12)	−0.0036 (14)	0.0044 (13)
C16	0.096 (2)	0.080 (2)	0.081 (2)	0.0307 (19)	0.0198 (18)	0.0376 (19)
C17	0.0329 (12)	0.075 (2)	0.0724 (18)	0.0058 (12)	−0.0040 (11)	−0.0046 (15)
N1	0.0322 (9)	0.0787 (17)	0.0521 (12)	0.0092 (10)	0.0048 (8)	0.0099 (12)
N2	0.0512 (12)	0.0504 (13)	0.0486 (12)	0.0059 (10)	0.0022 (9)	0.0078 (10)
N3	0.0485 (11)	0.0534 (13)	0.0506 (13)	0.0095 (10)	0.0044 (9)	0.0074 (10)
O1	0.0577 (10)	0.0845 (15)	0.0567 (11)	0.0191 (10)	0.0038 (9)	0.0243 (10)
O2	0.0494 (9)	0.0457 (10)	0.0726 (12)	−0.0038 (8)	0.0088 (9)	−0.0036 (9)
S1	0.0344 (3)	0.0471 (3)	0.0475 (3)	0.0042 (3)	0.0046 (2)	0.0087 (3)

C1—C2	1.389 (3)	C10—C11	1.400 (3)
C1—C6	1.392 (3)	C11—C12	1.369 (3)
C1—N1	1.413 (3)	C11—H11	0.9300
C2—C3	1.366 (4)	C12—C13	1.371 (4)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.371 (4)	C13—C14	1.372 (4)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.384 (4)	C14—C15	1.378 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.402 (3)	C15—H15	0.9300
C5—H5	0.9300	C16—H16A	0.9600
C6—C7	1.477 (3)	C16—H16B	0.9600
C7—N2	1.280 (3)	C16—H16C	0.9600
C7—C8	1.507 (3)	C17—N1	1.453 (3)
C8—S1	1.743 (2)	C17—H17A	0.9600
C8—H8A	0.9700	C17—H17B	0.9600
C8—H8B	0.9700	C17—H17C	0.9600
C9—N3	1.277 (3)	N1—S1	1.6402 (19)
C9—C10	1.483 (3)	N2—N3	1.392 (3)
C9—C16	1.491 (3)	O1—S1	1.4251 (18)
C10—C15	1.389 (3)	O2—S1	1.4288 (18)
C2—C1—C6	119.8 (2)	C11—C12—C13	120.5 (3)
C2—C1—N1	119.0 (2)	C11—C12—H12	119.8
C6—C1—N1	121.14 (19)	C13—C12—H12	119.8
C3—C2—C1	120.6 (3)	C14—C13—C12	119.7 (3)
C3—C2—H2	119.7	C14—C13—H13	120.1
C1—C2—H2	119.7	C12—C13—H13	120.1
C2—C3—C4	121.0 (3)	C13—C14—C15	120.2 (3)
C2—C3—H3	119.5	C13—C14—H14	119.9
C4—C3—H3	119.5	C15—C14—H14	119.9
C3—C4—C5	119.1 (3)	C14—C15—C10	121.1 (3)
C3—C4—H4	120.5	C14—C15—H15	119.4
C5—C4—H4	120.5	C10—C15—H15	119.4
C4—C5—C6	121.2 (3)	C9—C16—H16A	109.5
C4—C5—H5	119.4	C9—C16—H16B	109.5
C6—C5—H5	119.4	H16A—C16—H16B	109.5
C1—C6—C5	118.3 (2)	C9—C16—H16C	109.5
C1—C6—C7	123.0 (2)	H16A—C16—H16C	109.5
C5—C6—C7	118.8 (2)	H16B—C16—H16C	109.5
N2—C7—C6	118.8 (2)	N1—C17—H17A	109.5
N2—C7—C8	122.9 (2)	N1—C17—H17B	109.5
C6—C7—C8	118.23 (19)	H17A—C17—H17B	109.5
C7—C8—S1	110.21 (16)	N1—C17—H17C	109.5
C7—C8—H8A	109.6	H17A—C17—H17C	109.5
S1—C8—H8A	109.6	H17B—C17—H17C	109.5
C7—C8—H8B	109.6	C1—N1—C17	121.73 (19)
S1—C8—H8B	109.6	C1—N1—S1	117.79 (15)
H8A—C8—H8B	108.1	C17—N1—S1	119.25 (17)
N3—C9—C10	115.9 (2)	C7—N2—N3	113.76 (19)
N3—C9—C16	124.3 (2)	C9—N3—N2	115.0 (2)
C10—C9—C16	119.7 (2)	O1—S1—O2	118.72 (12)
C15—C10—C11	117.4 (2)	O1—S1—N1	107.15 (10)
C15—C10—C9	121.8 (2)	O2—S1—N1	110.61 (11)
C11—C10—C9	120.8 (2)	O1—S1—C8	111.07 (12)
C12—C11—C10	121.0 (2)	O2—S1—C8	107.78 (10)
C12—C11—H11	119.5	N1—S1—C8	99.87 (11)
C10—C11—H11	119.5
C6—C1—C2—C3	0.7 (4)	C11—C12—C13—C14	−1.0 (4)
N1—C1—C2—C3	179.1 (2)	C12—C13—C14—C15	0.7 (5)
C1—C2—C3—C4	1.4 (5)	C13—C14—C15—C10	−0.2 (5)
C2—C3—C4—C5	−1.5 (5)	C11—C10—C15—C14	−0.1 (4)
C3—C4—C5—C6	−0.5 (4)	C9—C10—C15—C14	−179.5 (2)
C2—C1—C6—C5	−2.6 (3)	C2—C1—N1—C17	−13.5 (4)
N1—C1—C6—C5	179.0 (2)	C6—C1—N1—C17	164.9 (2)
C2—C1—C6—C7	176.5 (2)	C2—C1—N1—S1	153.8 (2)
N1—C1—C6—C7	−1.8 (3)	C6—C1—N1—S1	−27.8 (3)
C4—C5—C6—C1	2.5 (4)	C6—C7—N2—N3	−179.38 (19)
C4—C5—C6—C7	−176.7 (2)	C8—C7—N2—N3	2.9 (3)
C1—C6—C7—N2	176.9 (2)	C10—C9—N3—N2	−178.1 (2)
C5—C6—C7—N2	−3.9 (3)	C16—C9—N3—N2	1.0 (4)
C1—C6—C7—C8	−5.3 (3)	C7—N2—N3—C9	−167.5 (2)
C5—C6—C7—C8	173.8 (2)	C1—N1—S1—O1	169.67 (19)
N2—C7—C8—S1	−145.02 (19)	C17—N1—S1—O1	−22.8 (2)
C6—C7—C8—S1	37.3 (2)	C1—N1—S1—O2	−59.5 (2)
N3—C9—C10—C15	170.5 (2)	C17—N1—S1—O2	108.0 (2)
C16—C9—C10—C15	−8.7 (4)	C1—N1—S1—C8	53.8 (2)
N3—C9—C10—C11	−8.9 (3)	C17—N1—S1—C8	−138.6 (2)
C16—C9—C10—C11	172.0 (3)	C7—C8—S1—O1	−169.41 (15)
C15—C10—C11—C12	−0.2 (4)	C7—C8—S1—O2	58.95 (17)
C9—C10—C11—C12	179.2 (2)	C7—C8—S1—N1	−56.59 (17)
C10—C11—C12—C13	0.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8B···O1i	0.97	2.56	3.420 (3)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8B⋯O1i	0.97	2.56	3.420 (3)	148

Symmetry code: (i) .