2-(3-Nitro-phen-yl)-3-phenyl-2,3-di-hydro-4H-1,3-benzo-thia-zin-4-one.

The title compound, C20H14N2O3S, has three aromatic rings, viz. (i) a phenyl ring, (ii) a 3-nitro-phenyl and (iii) a 1,3-benzo-thia-zine fused-ring system. The dihedral angle between (i) and (ii) is 85.31 (15)°, between (ii) and (iii) is 81.33 (15)° and between (i) and (iii) is 75.73 (15)°. The six-membered 1,3-thia-zine ring has an envelope conformation with the C atom in the 2-position forming the flap. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming a three-dimensional network.

Related literature

For amide bond formation using 2,4,6-tripropyl-1,3,5,2,4,6-trioxatri­phospho­rinane-2,4,6-trioxide (T3P), see: Dunetz et al. (2011 ▶). For preparation of various heterocycles using imines and T3P, see: Unsworth et al. (2013 ▶). For a review of 1,3-thia­zin-4-ones, see: Ryabukhin et al. (1996 ▶). For other 2,3-diaryl-2,3-di­hydro-1,3-benzo­thia­zin-4-ones, see: Kamel et al. (2010 ▶); Kollenz & Ziegler (1970 ▶); Oae & Numata (1974 ▶); Ponci et al. (1963 ▶); Zarghi et al. (2009 ▶).

Experimental

Crystal data

C20H14N2O3S

M = 362.39

Monoclinic,

a = 9.8741 (13) Å

b = 13.0544 (18) Å

c = 13.365 (2) Å

β = 100.878 (4)°

V = 1691.7 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.22 mm−1

T = 298 K

0.27 × 0.25 × 0.24 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.945, T max = 0.951

9929 measured reflections

2904 independent reflections

2578 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.04

2904 reflections

235 parameters

H-atom parameters not refined

Δρmax = 0.16 e Å−3

Δρmin = −2.21 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2001 ▶); software used to prepare material for publication: ORTEP-3 for Windows (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813028389/fy2105sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813028389/fy2105Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028389/fy2105Isup3.mol

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813028389/fy2105Isup4.cml

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

C20H14N2O3S	Dx = 1.423 Mg m−3
Mr = 362.39	Melting point: 436 K
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8741 (13) Å	Cell parameters from 3778 reflections
b = 13.0544 (18) Å	θ = 2.2–28.2°
c = 13.365 (2) Å	µ = 0.22 mm−1
β = 100.878 (4)°	T = 298 K
V = 1691.7 (4) Å3	Block, colorless
Z = 4	0.27 × 0.25 × 0.24 mm
F(000) = 752

Bruker SMART-APEX CCD diffractometer	2904 independent reflections
Radiation source: fine-focus sealed tube	2572 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 8.34 pixels mm-1	θmax = 25.0°, θmin = 2.2°
φ and ω scans	h = −11→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −14→15
Tmin = 0.944, Tmax = 0.950	l = −15→15
9929 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters not refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.3773P] where P = (Fo2 + 2Fc2)/3
2904 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm. SADABS was used for absorption correction. R(int) was 0.0320 before and 0.0220 after correction. The Ratio of minimum to maximum transmission is 0.8417. The λ/2 correction factor is 0.0015.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.14364 (16)	0.21740 (11)	0.36136 (10)	0.0386 (3)
C2	0.22760 (15)	0.17463 (11)	0.30037 (10)	0.0360 (3)
H2	0.3208	0.1912	0.3105	0.043*
C3	0.17090 (14)	0.10692 (11)	0.22415 (10)	0.0342 (3)
C4	0.03139 (16)	0.08233 (13)	0.21336 (12)	0.0457 (4)
H4	−0.0081	0.0371	0.1624	0.055*
C5	−0.04918 (17)	0.12405 (15)	0.27706 (14)	0.0538 (4)
H5	−0.1415	0.1054	0.2696	0.065*
C6	0.00665 (17)	0.19323 (13)	0.35175 (12)	0.0477 (4)
H6	−0.0471	0.2225	0.3943	0.057*
C7	0.25569 (14)	0.05832 (12)	0.15304 (10)	0.0362 (3)
H7	0.2442	−0.0160	0.1579	0.043*
C8	0.49204 (14)	−0.00021 (11)	0.23007 (10)	0.0346 (3)
C9	0.45797 (17)	−0.05383 (13)	0.31141 (12)	0.0436 (4)
H9	0.3771	−0.0386	0.3344	0.052*
C10	0.54491 (18)	−0.13033 (13)	0.35838 (12)	0.0504 (4)
H10	0.5214	−0.1671	0.4122	0.060*
C11	0.66539 (18)	−0.15198 (13)	0.32568 (12)	0.0493 (4)
H11	0.7248	−0.2019	0.3585	0.059*
C12	0.69799 (16)	−0.09922 (13)	0.24379 (12)	0.0464 (4)
H12	0.7790	−0.1147	0.2211	0.056*
C13	0.61167 (16)	−0.02387 (12)	0.19526 (11)	0.0402 (3)
H13	0.6338	0.0107	0.1396	0.048*
C14	0.45482 (14)	0.17527 (11)	0.16948 (10)	0.0345 (3)
C15	0.36533 (15)	0.24938 (11)	0.10216 (10)	0.0357 (3)
C16	0.40628 (17)	0.35182 (12)	0.10646 (12)	0.0445 (4)
H16	0.4810	0.3725	0.1556	0.053*
C17	0.3380 (2)	0.42271 (14)	0.03930 (13)	0.0535 (4)
H17	0.3657	0.4909	0.0437	0.064*
C18	0.2281 (2)	0.39235 (15)	−0.03486 (13)	0.0560 (5)
H18	0.1839	0.4399	−0.0818	0.067*
C19	0.18368 (17)	0.29236 (15)	−0.03962 (11)	0.0502 (4)
H19	0.1089	0.2728	−0.0892	0.060*
C20	0.25026 (15)	0.22016 (12)	0.02946 (10)	0.0393 (4)
N1	0.20361 (17)	0.29450 (10)	0.43715 (10)	0.0481 (3)
N2	0.40305 (12)	0.07868 (9)	0.17982 (9)	0.0355 (3)
O1	0.12985 (17)	0.33388 (12)	0.48963 (10)	0.0775 (4)
O2	0.32476 (15)	0.31730 (11)	0.44327 (11)	0.0690 (4)
O3	0.57097 (11)	0.19924 (8)	0.21252 (8)	0.0449 (3)
S1	0.19079 (4)	0.09311 (3)	0.02046 (3)	0.04701 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0458 (9)	0.0348 (8)	0.0366 (7)	0.0022 (6)	0.0111 (6)	0.0069 (6)
C2	0.0328 (7)	0.0382 (8)	0.0374 (7)	−0.0008 (6)	0.0076 (6)	0.0051 (6)
C3	0.0313 (7)	0.0341 (8)	0.0371 (7)	−0.0008 (6)	0.0063 (6)	0.0042 (6)
C4	0.0368 (8)	0.0472 (10)	0.0530 (9)	−0.0085 (7)	0.0088 (7)	−0.0021 (7)
C5	0.0349 (8)	0.0632 (11)	0.0672 (11)	−0.0059 (8)	0.0193 (8)	0.0036 (9)
C6	0.0474 (9)	0.0488 (10)	0.0524 (9)	0.0053 (8)	0.0236 (7)	0.0068 (7)
C7	0.0315 (8)	0.0348 (8)	0.0413 (7)	−0.0033 (6)	0.0041 (6)	−0.0027 (6)
C8	0.0318 (7)	0.0348 (8)	0.0365 (7)	0.0003 (6)	0.0050 (6)	−0.0026 (6)
C9	0.0398 (8)	0.0447 (9)	0.0491 (8)	0.0002 (7)	0.0158 (7)	0.0032 (7)
C10	0.0570 (10)	0.0462 (10)	0.0491 (9)	−0.0009 (8)	0.0130 (8)	0.0109 (7)
C11	0.0498 (10)	0.0430 (10)	0.0522 (9)	0.0100 (8)	0.0020 (7)	0.0033 (7)
C12	0.0369 (8)	0.0503 (10)	0.0525 (9)	0.0082 (7)	0.0102 (7)	−0.0031 (7)
C13	0.0384 (8)	0.0446 (9)	0.0387 (7)	0.0032 (7)	0.0101 (6)	0.0016 (6)
C14	0.0341 (8)	0.0385 (8)	0.0316 (7)	−0.0021 (6)	0.0082 (6)	−0.0016 (6)
C15	0.0362 (8)	0.0400 (9)	0.0323 (7)	0.0016 (6)	0.0103 (6)	−0.0007 (6)
C16	0.0483 (9)	0.0422 (9)	0.0445 (8)	0.0014 (7)	0.0126 (7)	−0.0003 (7)
C17	0.0640 (11)	0.0416 (10)	0.0594 (10)	0.0098 (8)	0.0227 (9)	0.0079 (7)
C18	0.0591 (11)	0.0615 (12)	0.0504 (9)	0.0228 (9)	0.0185 (8)	0.0185 (8)
C19	0.0417 (9)	0.0724 (13)	0.0366 (8)	0.0123 (8)	0.0071 (7)	0.0065 (7)
C20	0.0358 (8)	0.0519 (10)	0.0315 (7)	0.0048 (7)	0.0101 (6)	−0.0012 (6)
N1	0.0650 (10)	0.0413 (8)	0.0393 (7)	0.0036 (7)	0.0134 (7)	0.0025 (6)
N2	0.0288 (6)	0.0365 (7)	0.0411 (6)	0.0009 (5)	0.0064 (5)	0.0003 (5)
O1	0.0956 (11)	0.0797 (10)	0.0658 (8)	0.0015 (8)	0.0373 (8)	−0.0239 (7)
O2	0.0631 (9)	0.0687 (9)	0.0741 (9)	−0.0121 (7)	0.0103 (7)	−0.0241 (7)
O3	0.0368 (6)	0.0479 (7)	0.0465 (6)	−0.0081 (5)	−0.0013 (5)	0.0042 (5)
S1	0.0444 (2)	0.0576 (3)	0.0362 (2)	−0.00628 (18)	0.00036 (17)	−0.00963 (16)

C1—C6	1.371 (2)	C11—C12	1.382 (2)
C1—C2	1.385 (2)	C11—H11	0.9300
C1—N1	1.471 (2)	C12—C13	1.381 (2)
C2—C3	1.385 (2)	C12—H12	0.9300
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.395 (2)	C14—O3	1.2227 (17)
C3—C7	1.519 (2)	C14—N2	1.3773 (19)
C4—C5	1.382 (2)	C14—C15	1.492 (2)
C4—H4	0.9300	C15—C16	1.395 (2)
C5—C6	1.381 (3)	C15—C20	1.401 (2)
C5—H5	0.9300	C16—C17	1.374 (2)
C6—H6	0.9300	C16—H16	0.9300
C7—N2	1.4558 (18)	C17—C18	1.383 (3)
C7—S1	1.8242 (14)	C17—H17	0.9300
C7—H7	0.9800	C18—C19	1.375 (3)
C8—C13	1.384 (2)	C18—H18	0.9300
C8—C9	1.387 (2)	C19—C20	1.394 (2)
C8—N2	1.4356 (18)	C19—H19	0.9300
C9—C10	1.387 (2)	C20—S1	1.7560 (17)
C9—H9	0.9300	N1—O1	1.2163 (19)
C10—C11	1.372 (2)	N1—O2	1.2203 (19)
C10—H10	0.9300
C6—C1—C2	122.79 (15)	C12—C11—H11	120.2
C6—C1—N1	118.93 (14)	C13—C12—C11	120.79 (15)
C2—C1—N1	118.24 (14)	C13—C12—H12	119.6
C3—C2—C1	119.11 (14)	C11—C12—H12	119.6
C3—C2—H2	120.4	C12—C13—C8	119.45 (14)
C1—C2—H2	120.4	C12—C13—H13	120.3
C2—C3—C4	118.50 (14)	C8—C13—H13	120.3
C2—C3—C7	122.20 (13)	O3—C14—N2	121.34 (13)
C4—C3—C7	119.29 (13)	O3—C14—C15	120.92 (13)
C5—C4—C3	121.17 (15)	N2—C14—C15	117.73 (12)
C5—C4—H4	119.4	C16—C15—C20	118.70 (14)
C3—C4—H4	119.4	C16—C15—C14	117.55 (13)
C6—C5—C4	120.34 (15)	C20—C15—C14	123.51 (14)
C6—C5—H5	119.8	C17—C16—C15	121.06 (16)
C4—C5—H5	119.8	C17—C16—H16	119.5
C1—C6—C5	118.05 (15)	C15—C16—H16	119.5
C1—C6—H6	121.0	C16—C17—C18	119.82 (17)
C5—C6—H6	121.0	C16—C17—H17	120.1
N2—C7—C3	114.41 (11)	C18—C17—H17	120.1
N2—C7—S1	110.18 (10)	C19—C18—C17	120.38 (16)
C3—C7—S1	111.69 (10)	C19—C18—H18	119.8
N2—C7—H7	106.7	C17—C18—H18	119.8
C3—C7—H7	106.7	C18—C19—C20	120.32 (16)
S1—C7—H7	106.7	C18—C19—H19	119.8
C13—C8—C9	119.98 (14)	C20—C19—H19	119.8
C13—C8—N2	119.27 (13)	C19—C20—C15	119.63 (15)
C9—C8—N2	120.74 (13)	C19—C20—S1	118.90 (12)
C8—C9—C10	119.81 (15)	C15—C20—S1	121.43 (11)
C8—C9—H9	120.1	O1—N1—O2	122.98 (15)
C10—C9—H9	120.1	O1—N1—C1	118.64 (16)
C11—C10—C9	120.25 (15)	O2—N1—C1	118.37 (14)
C11—C10—H10	119.9	C14—N2—C8	119.85 (11)
C9—C10—H10	119.9	C14—N2—C7	121.01 (12)
C10—C11—C12	119.69 (15)	C8—N2—C7	118.63 (12)
C10—C11—H11	120.2	C20—S1—C7	96.72 (7)
C6—C1—C2—C3	2.1 (2)	C16—C17—C18—C19	2.2 (3)
N1—C1—C2—C3	−175.83 (12)	C17—C18—C19—C20	−0.9 (3)
C1—C2—C3—C4	−1.6 (2)	C18—C19—C20—C15	−1.8 (2)
C1—C2—C3—C7	178.93 (13)	C18—C19—C20—S1	−179.74 (12)
C2—C3—C4—C5	−0.1 (2)	C16—C15—C20—C19	3.0 (2)
C7—C3—C4—C5	179.38 (15)	C14—C15—C20—C19	−171.23 (13)
C3—C4—C5—C6	1.5 (3)	C16—C15—C20—S1	−179.07 (11)
C2—C1—C6—C5	−0.7 (2)	C14—C15—C20—S1	6.68 (19)
N1—C1—C6—C5	177.16 (14)	C6—C1—N1—O1	0.6 (2)
C4—C5—C6—C1	−1.0 (3)	C2—C1—N1—O1	178.58 (14)
C2—C3—C7—N2	7.31 (19)	C6—C1—N1—O2	−178.18 (14)
C4—C3—C7—N2	−172.17 (13)	C2—C1—N1—O2	−0.2 (2)
C2—C3—C7—S1	−118.72 (13)	O3—C14—N2—C8	−8.7 (2)
C4—C3—C7—S1	61.80 (16)	C15—C14—N2—C8	170.05 (12)
C13—C8—C9—C10	0.7 (2)	O3—C14—N2—C7	162.90 (13)
N2—C8—C9—C10	179.50 (14)	C15—C14—N2—C7	−18.30 (18)
C8—C9—C10—C11	1.0 (2)	C13—C8—N2—C14	−55.44 (18)
C9—C10—C11—C12	−1.8 (3)	C9—C8—N2—C14	125.78 (15)
C10—C11—C12—C13	0.9 (3)	C13—C8—N2—C7	132.72 (14)
C11—C12—C13—C8	0.8 (2)	C9—C8—N2—C7	−46.06 (18)
C9—C8—C13—C12	−1.6 (2)	C3—C7—N2—C14	−69.47 (16)
N2—C8—C13—C12	179.58 (13)	S1—C7—N2—C14	57.35 (15)
O3—C14—C15—C16	−12.9 (2)	C3—C7—N2—C8	102.28 (14)
N2—C14—C15—C16	168.26 (13)	S1—C7—N2—C8	−130.90 (11)
O3—C14—C15—C20	161.39 (14)	C19—C20—S1—C7	−155.36 (12)
N2—C14—C15—C20	−17.4 (2)	C15—C20—S1—C7	26.72 (13)
C20—C15—C16—C17	−1.7 (2)	N2—C7—S1—C20	−54.94 (11)
C14—C15—C16—C17	172.90 (14)	C3—C7—S1—C20	73.38 (11)
C15—C16—C17—C18	−0.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···O3i	0.93	2.63	3.2912 (19)	129
C7—H7···O2ii	0.98	2.59	3.435 (2)	145
C11—H11···O3iii	0.93	2.71	3.363 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯O3i	0.93	2.67	3.334 (8)	129
C7—H7⋯O2ii	0.98	2.58	3.424 (8)	145
C11—H11⋯O3iii	0.93	2.71	3.362 (6)	128

Symmetry codes: (i) ; (ii) ; (iii) .