4-[2-(Anthracen-9-yl-methyl-idene)hydrazinyl-idene]-3-chloro-1-methyl-3,4-dihydro-1H-2λ(6),1-benzothia-zine-2,2-dione.

In the title compound, C(24)H(18)ClN(3)O(2)S, the dihedral angle between the benzene ring and the anthracene ring system is 41.10 (8)°. The thia-zine ring has a half-chair conformation and the Cl atom is in an axial orientation. In the crystal, mol-ecules are linked by C-H⋯O inter-actions, generating C(8) chains along [100]. A C-H⋯N short contact occurs in the mol-ecule, generating an S(6) ring.

Related literature

For a related structure and references to further synthetic details, see: Shafiq et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C24H18ClN3O2S

M = 447.92

Monoclinic,

a = 8.5133 (4) Å

b = 19.8999 (8) Å

c = 12.7849 (6) Å

β = 105.026 (2)°

V = 2091.88 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 296 K

0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.930, T max = 0.960

16154 measured reflections

3788 independent reflections

2827 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.136

S = 1.04

3788 reflections

281 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.35 e Å−3

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/S1600536812021642/hb6779sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812021642/hb6779Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812021642/hb6779Isup3.cml

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

C24H18ClN3O2S	F(000) = 928
Mr = 447.92	Dx = 1.422 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2827 reflections
a = 8.5133 (4) Å	θ = 2.1–25.3°
b = 19.8999 (8) Å	µ = 0.31 mm−1
c = 12.7849 (6) Å	T = 296 K
β = 105.026 (2)°	Prism, orange
V = 2091.88 (16) Å3	0.26 × 0.22 × 0.20 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	3788 independent reflections
Radiation source: fine-focus sealed tube	2827 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.031
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.1°
ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −23→18
Tmin = 0.930, Tmax = 0.960	l = −15→15
16154 measured reflections

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0652P)2 + 0.8876P] where P = (Fo2 + 2Fc2)/3
3788 reflections	(Δ/σ)max = 0.001
281 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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	0.31773 (12)	0.02405 (4)	0.89027 (7)	0.0772 (3)
S1	0.47338 (9)	0.15552 (4)	0.89884 (6)	0.0561 (3)
O1	0.6215 (3)	0.12587 (13)	0.95945 (17)	0.0790 (8)
O2	0.4770 (2)	0.20988 (10)	0.82508 (16)	0.0625 (7)
N1	0.3657 (3)	0.17603 (12)	0.98246 (17)	0.0581 (8)
N2	0.1106 (3)	0.12240 (10)	0.66521 (16)	0.0470 (7)
N3	0.1929 (3)	0.07899 (11)	0.61082 (16)	0.0520 (8)
C1	0.1136 (3)	0.17431 (11)	0.8339 (2)	0.0436 (8)
C2	−0.0466 (3)	0.19551 (13)	0.7960 (2)	0.0533 (9)
C3	−0.1214 (4)	0.23414 (14)	0.8580 (3)	0.0632 (11)
C4	−0.0340 (4)	0.25376 (14)	0.9606 (3)	0.0665 (13)
C5	0.1253 (4)	0.23567 (14)	0.9993 (2)	0.0596 (10)
C6	0.2010 (4)	0.19540 (13)	0.9382 (2)	0.0498 (9)
C7	0.3445 (3)	0.09596 (13)	0.8164 (2)	0.0485 (8)
C8	0.1851 (3)	0.13033 (12)	0.76582 (18)	0.0414 (8)
C9	0.1181 (3)	0.07213 (12)	0.51179 (19)	0.0456 (8)
C10	0.1765 (3)	0.03012 (12)	0.43534 (19)	0.0430 (8)
C11	0.1245 (3)	0.04805 (12)	0.32402 (19)	0.0456 (8)
C12	0.0261 (4)	0.10529 (14)	0.2848 (2)	0.0619 (10)
C13	−0.0196 (4)	0.12103 (16)	0.1775 (2)	0.0676 (10)
C14	0.0306 (4)	0.08209 (16)	0.1014 (2)	0.0667 (10)
C15	0.1244 (4)	0.02818 (15)	0.1340 (2)	0.0603 (10)
C16	0.1755 (3)	0.00887 (13)	0.2453 (2)	0.0473 (8)
C17	0.2714 (3)	−0.04692 (13)	0.2787 (2)	0.0534 (10)
C18	0.3237 (3)	−0.06616 (12)	0.3865 (2)	0.0490 (9)
C19	0.4221 (4)	−0.12438 (15)	0.4175 (3)	0.0641 (11)
C20	0.4705 (4)	−0.14389 (16)	0.5208 (3)	0.0742 (13)
C21	0.4206 (4)	−0.10726 (15)	0.6017 (3)	0.0723 (11)
C22	0.3269 (4)	−0.05134 (14)	0.5762 (2)	0.0596 (10)
C23	0.2760 (3)	−0.02744 (12)	0.4675 (2)	0.0447 (8)
C24	0.4352 (5)	0.1704 (2)	1.0998 (2)	0.0851 (15)
H2	−0.10484	0.18318	0.72662	0.0639*
H3	−0.22948	0.24698	0.83144	0.0757*
H4	−0.08417	0.27945	1.00339	0.0798*
H5	0.18372	0.25048	1.06725	0.0716*
H7	0.39378	0.08215	0.75851	0.0582*
H9	0.02056	0.09509	0.48613	0.0547*
H12	−0.00791	0.13259	0.33383	0.0744*
H13	−0.08517	0.15836	0.15457	0.0813*
H14	−0.00106	0.09351	0.02836	0.0801*
H15	0.15741	0.00253	0.08271	0.0725*
H17	0.30231	−0.07276	0.22679	0.0640*
H19	0.45336	−0.14929	0.36469	0.0764*
H20	0.53679	−0.18145	0.53962	0.0887*
H21	0.45241	−0.12174	0.67323	0.0865*
H22	0.29546	−0.02823	0.63070	0.0713*
H24A	0.46719	0.21406	1.12959	0.1277*
H24B	0.52845	0.14138	1.11401	0.1277*
H24C	0.35525	0.15194	1.13268	0.1277*

	U11	U22	U33	U12	U13	U23
Cl1	0.1028 (7)	0.0585 (5)	0.0677 (5)	0.0011 (4)	0.0176 (5)	0.0132 (4)
S1	0.0554 (4)	0.0686 (5)	0.0428 (4)	−0.0061 (3)	0.0100 (3)	−0.0092 (3)
O1	0.0610 (13)	0.1054 (17)	0.0592 (13)	0.0087 (12)	−0.0049 (10)	−0.0130 (12)
O2	0.0646 (13)	0.0666 (12)	0.0617 (12)	−0.0183 (10)	0.0263 (10)	−0.0031 (10)
N1	0.0694 (16)	0.0683 (15)	0.0333 (12)	−0.0026 (12)	0.0076 (11)	−0.0079 (11)
N2	0.0551 (13)	0.0515 (12)	0.0352 (11)	0.0019 (10)	0.0131 (10)	−0.0046 (9)
N3	0.0600 (14)	0.0615 (13)	0.0347 (12)	0.0041 (11)	0.0127 (10)	−0.0103 (10)
C1	0.0547 (16)	0.0401 (13)	0.0410 (14)	−0.0090 (11)	0.0215 (12)	−0.0026 (11)
C2	0.0561 (17)	0.0506 (15)	0.0574 (17)	−0.0084 (13)	0.0225 (14)	−0.0053 (13)
C3	0.0625 (19)	0.0526 (16)	0.085 (2)	−0.0038 (14)	0.0378 (17)	−0.0041 (16)
C4	0.095 (3)	0.0477 (16)	0.075 (2)	−0.0053 (16)	0.055 (2)	−0.0096 (15)
C5	0.091 (2)	0.0487 (16)	0.0480 (16)	−0.0079 (15)	0.0339 (16)	−0.0090 (13)
C6	0.0706 (19)	0.0436 (14)	0.0406 (14)	−0.0100 (13)	0.0239 (13)	−0.0041 (11)
C7	0.0562 (16)	0.0547 (15)	0.0354 (13)	−0.0003 (12)	0.0132 (12)	−0.0057 (11)
C8	0.0504 (15)	0.0433 (13)	0.0330 (13)	−0.0080 (11)	0.0152 (11)	−0.0037 (10)
C9	0.0561 (16)	0.0464 (14)	0.0343 (13)	−0.0019 (12)	0.0120 (12)	−0.0022 (11)
C10	0.0514 (15)	0.0441 (13)	0.0337 (13)	−0.0074 (11)	0.0114 (11)	−0.0054 (10)
C11	0.0569 (16)	0.0455 (14)	0.0335 (13)	−0.0095 (12)	0.0103 (11)	−0.0059 (11)
C12	0.089 (2)	0.0559 (16)	0.0392 (15)	0.0073 (15)	0.0136 (14)	−0.0011 (13)
C13	0.094 (2)	0.0603 (17)	0.0434 (16)	0.0009 (16)	0.0084 (16)	0.0050 (14)
C14	0.096 (2)	0.0651 (19)	0.0341 (15)	−0.0196 (18)	0.0083 (15)	0.0018 (14)
C15	0.083 (2)	0.0653 (18)	0.0354 (14)	−0.0200 (16)	0.0202 (14)	−0.0123 (13)
C16	0.0590 (16)	0.0473 (14)	0.0371 (13)	−0.0133 (12)	0.0154 (12)	−0.0083 (11)
C17	0.0653 (18)	0.0554 (16)	0.0461 (16)	−0.0120 (14)	0.0265 (13)	−0.0138 (13)
C18	0.0510 (16)	0.0436 (14)	0.0555 (17)	−0.0076 (12)	0.0192 (13)	−0.0077 (12)
C19	0.072 (2)	0.0532 (16)	0.073 (2)	0.0051 (15)	0.0296 (17)	−0.0012 (15)
C20	0.078 (2)	0.0541 (18)	0.090 (3)	0.0105 (16)	0.0211 (19)	0.0066 (17)
C21	0.089 (2)	0.0621 (19)	0.0595 (19)	0.0060 (17)	0.0081 (17)	0.0120 (15)
C22	0.077 (2)	0.0533 (16)	0.0454 (16)	0.0013 (14)	0.0103 (14)	0.0003 (13)
C23	0.0504 (15)	0.0436 (13)	0.0386 (13)	−0.0086 (11)	0.0086 (11)	−0.0028 (11)
C24	0.092 (3)	0.124 (3)	0.0344 (16)	−0.008 (2)	0.0078 (16)	−0.0069 (18)

Cl1—C7	1.762 (3)	C16—C17	1.379 (4)
S1—O1	1.426 (3)	C17—C18	1.388 (3)
S1—O2	1.441 (2)	C18—C19	1.424 (4)
S1—N1	1.630 (3)	C18—C23	1.432 (4)
S1—C7	1.766 (3)	C19—C20	1.335 (5)
N1—C6	1.423 (4)	C20—C21	1.418 (5)
N1—C24	1.467 (3)	C21—C22	1.359 (4)
N2—N3	1.405 (3)	C22—C23	1.426 (4)
N2—C8	1.288 (3)	C2—H2	0.9300
N3—C9	1.269 (3)	C3—H3	0.9300
C1—C2	1.389 (4)	C4—H4	0.9300
C1—C6	1.412 (4)	C5—H5	0.9300
C1—C8	1.473 (3)	C7—H7	0.9800
C2—C3	1.374 (4)	C9—H9	0.9300
C3—C4	1.386 (5)	C12—H12	0.9300
C4—C5	1.366 (5)	C13—H13	0.9300
C5—C6	1.389 (4)	C14—H14	0.9300
C7—C8	1.508 (4)	C15—H15	0.9300
C9—C10	1.467 (3)	C17—H17	0.9300
C10—C11	1.422 (3)	C19—H19	0.9300
C10—C23	1.421 (3)	C20—H20	0.9300
C11—C12	1.426 (4)	C21—H21	0.9300
C11—C16	1.427 (4)	C22—H22	0.9300
C12—C13	1.362 (4)	C24—H24A	0.9600
C13—C14	1.395 (4)	C24—H24B	0.9600
C14—C15	1.338 (4)	C24—H24C	0.9600
C15—C16	1.429 (4)
O1—S1—O2	120.04 (14)	C18—C19—C20	121.3 (3)
O1—S1—N1	108.40 (13)	C19—C20—C21	119.9 (3)
O1—S1—C7	111.82 (14)	C20—C21—C22	121.0 (3)
O2—S1—N1	110.63 (12)	C21—C22—C23	121.2 (3)
O2—S1—C7	103.22 (12)	C10—C23—C18	119.0 (2)
N1—S1—C7	101.03 (13)	C10—C23—C22	124.0 (2)
S1—N1—C6	118.09 (17)	C18—C23—C22	117.0 (2)
S1—N1—C24	120.3 (2)	C1—C2—H2	119.00
C6—N1—C24	121.5 (3)	C3—C2—H2	119.00
N3—N2—C8	113.0 (2)	C2—C3—H3	120.00
N2—N3—C9	112.0 (2)	C4—C3—H3	120.00
C2—C1—C6	117.9 (2)	C3—C4—H4	120.00
C2—C1—C8	119.6 (2)	C5—C4—H4	120.00
C6—C1—C8	122.5 (2)	C4—C5—H5	120.00
C1—C2—C3	121.9 (3)	C6—C5—H5	120.00
C2—C3—C4	119.2 (3)	Cl1—C7—H7	109.00
C3—C4—C5	120.5 (3)	S1—C7—H7	109.00
C4—C5—C6	120.7 (3)	C8—C7—H7	108.00
N1—C6—C1	121.3 (2)	N3—C9—H9	118.00
N1—C6—C5	119.1 (2)	C10—C9—H9	118.00
C1—C6—C5	119.7 (3)	C11—C12—H12	119.00
Cl1—C7—S1	111.83 (14)	C13—C12—H12	119.00
Cl1—C7—C8	111.80 (18)	C12—C13—H13	120.00
S1—C7—C8	107.60 (17)	C14—C13—H13	119.00
N2—C8—C1	119.4 (2)	C13—C14—H14	120.00
N2—C8—C7	121.9 (2)	C15—C14—H14	120.00
C1—C8—C7	118.7 (2)	C14—C15—H15	119.00
N3—C9—C10	123.9 (2)	C16—C15—H15	119.00
C9—C10—C11	116.9 (2)	C16—C17—H17	119.00
C9—C10—C23	123.1 (2)	C18—C17—H17	119.00
C11—C10—C23	120.0 (2)	C18—C19—H19	119.00
C10—C11—C12	123.7 (2)	C20—C19—H19	119.00
C10—C11—C16	119.7 (2)	C19—C20—H20	120.00
C12—C11—C16	116.6 (2)	C21—C20—H20	120.00
C11—C12—C13	121.8 (3)	C20—C21—H21	119.00
C12—C13—C14	121.1 (3)	C22—C21—H21	120.00
C13—C14—C15	119.6 (2)	C21—C22—H22	119.00
C14—C15—C16	121.9 (3)	C23—C22—H22	119.00
C11—C16—C15	119.1 (2)	N1—C24—H24A	110.00
C11—C16—C17	119.1 (2)	N1—C24—H24B	110.00
C15—C16—C17	121.9 (2)	N1—C24—H24C	109.00
C16—C17—C18	122.8 (2)	H24A—C24—H24B	110.00
C17—C18—C19	121.0 (3)	H24A—C24—H24C	109.00
C17—C18—C23	119.5 (2)	H24B—C24—H24C	109.00
C19—C18—C23	119.6 (2)
O1—S1—N1—C6	−169.0 (2)	S1—C7—C8—C1	−43.3 (3)
O1—S1—N1—C24	7.3 (3)	N3—C9—C10—C11	−154.0 (3)
O2—S1—N1—C6	57.5 (2)	N3—C9—C10—C23	28.1 (4)
O2—S1—N1—C24	−126.2 (2)	C9—C10—C11—C12	2.7 (4)
C7—S1—N1—C6	−51.3 (2)	C9—C10—C11—C16	−179.4 (2)
C7—S1—N1—C24	125.0 (3)	C23—C10—C11—C12	−179.3 (3)
O1—S1—C7—Cl1	50.62 (19)	C23—C10—C11—C16	−1.3 (4)
O1—S1—C7—C8	173.77 (17)	C9—C10—C23—C18	178.5 (2)
O2—S1—C7—Cl1	−178.99 (14)	C9—C10—C23—C22	1.3 (4)
O2—S1—C7—C8	−55.85 (19)	C11—C10—C23—C18	0.7 (4)
N1—S1—C7—Cl1	−64.50 (17)	C11—C10—C23—C22	−176.6 (3)
N1—S1—C7—C8	58.64 (19)	C10—C11—C12—C13	179.3 (3)
S1—N1—C6—C1	23.8 (3)	C16—C11—C12—C13	1.3 (4)
S1—N1—C6—C5	−156.4 (2)	C10—C11—C16—C15	−179.0 (3)
C24—N1—C6—C1	−152.4 (3)	C10—C11—C16—C17	1.6 (4)
C24—N1—C6—C5	27.4 (4)	C12—C11—C16—C15	−0.9 (4)
C8—N2—N3—C9	−179.6 (2)	C12—C11—C16—C17	179.8 (3)
N3—N2—C8—C1	−179.8 (2)	C11—C12—C13—C14	−1.0 (5)
N3—N2—C8—C7	0.4 (3)	C12—C13—C14—C15	0.4 (5)
N2—N3—C9—C10	179.6 (2)	C13—C14—C15—C16	0.0 (5)
C6—C1—C2—C3	−1.9 (4)	C14—C15—C16—C11	0.3 (5)
C8—C1—C2—C3	177.1 (2)	C14—C15—C16—C17	179.6 (3)
C2—C1—C6—N1	−179.7 (2)	C11—C16—C17—C18	−1.3 (4)
C2—C1—C6—C5	0.5 (4)	C15—C16—C17—C18	179.3 (3)
C8—C1—C6—N1	1.3 (4)	C16—C17—C18—C19	179.7 (3)
C8—C1—C6—C5	−178.6 (2)	C16—C17—C18—C23	0.6 (4)
C2—C1—C8—N2	13.1 (4)	C17—C18—C19—C20	−178.8 (3)
C2—C1—C8—C7	−167.1 (2)	C23—C18—C19—C20	0.3 (5)
C6—C1—C8—N2	−167.9 (2)	C17—C18—C23—C10	−0.3 (4)
C6—C1—C8—C7	11.9 (4)	C17—C18—C23—C22	177.1 (3)
C1—C2—C3—C4	1.3 (4)	C19—C18—C23—C10	−179.4 (3)
C2—C3—C4—C5	0.8 (5)	C19—C18—C23—C22	−2.0 (4)
C3—C4—C5—C6	−2.2 (5)	C18—C19—C20—C21	1.5 (5)
C4—C5—C6—N1	−178.2 (3)	C19—C20—C21—C22	−1.6 (5)
C4—C5—C6—C1	1.6 (4)	C20—C21—C22—C23	−0.2 (5)
Cl1—C7—C8—N2	−100.3 (3)	C21—C22—C23—C10	179.2 (3)
Cl1—C7—C8—C1	79.9 (2)	C21—C22—C23—C18	1.9 (4)
S1—C7—C8—N2	136.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.59	3.370 (4)	142
C22—H22···N3	0.93	2.29	2.913 (4)	123

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.59	3.370 (4)	142
C22—H22⋯N3	0.93	2.29	2.913 (4)	123

Symmetry code: (i) .