2,3-Diphenyl-2,3-di-hydro-4H-pyrido[3,2-e][1,3]thia-zin-4-one.

In the racemic title compound, C19H14N2OS, the two phenyl substituents on the 1,3-thia-zine ring are almost perpendicular to the pyridine ring which is fused to the thia-zine ring [inter-ring dihedral angles = 87.90 (8) and 85.54 (7)°]. The dihedral angle between the two phenyl rings is 75.11 (7)°. The six-membered thia-zine ring has an envelope conformation with the ortho-related C atom forming the flap. The crystals exhibit face-to-edge aromatic-ring interactions with the nearest C-H⋯C distance equal to 3.676 (3) Å.

Related literature

For the syntheses and crystal structures of related compounds, see: Yennawar et al. (2013 ▶, 2014 ▶); Yennawar & Silverberg (2013 ▶, 2014 ▶). For the formation of amide bonds using 2,4,6-tripropyl-1,3,5,2,4,6-trioxatri­phospho­rinane-2,4,6-trioxide (T3P) and pyridine, see: Dunetz et al. (2011 ▶). For the microwave-promoted reaction of an N-aryl imine with 2-thio­nicotinic acid, see: Dandia et al. (2004 ▶).

Experimental

Crystal data

C19H14N2OS

M = 318.38

Triclinic,

a = 9.069 (7) Å

b = 9.772 (7) Å

c = 10.150 (7) Å

α = 80.320 (11)°

β = 63.737 (10)°

γ = 78.591 (12)°

V = 787.4 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.29 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.941, T max = 0.959

7363 measured reflections

3795 independent reflections

3322 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.114

S = 1.05

3795 reflections

208 parameters

H-atom parameters not refined

Δρmax = 0.34 e Å−3

Δρmin = −0.28 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/S1600536814009714/zs2297sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814009714/zs2297Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009714/zs2297Isup3.mol

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814009714/zs2297Isup4.cml

CCDC reference: 1000248

Additional supporting information: crystallographic information; 3D view; checkCIF report

C19H14N2OS	Z = 2
Mr = 318.38	F(000) = 332
Triclinic, P1	Dx = 1.343 Mg m−3
Hall symbol: -P 1	Melting point: 407.5 K
a = 9.069 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.772 (7) Å	Cell parameters from 4119 reflections
c = 10.150 (7) Å	θ = 2.3–28.2°
α = 80.320 (11)°	µ = 0.21 mm−1
β = 63.737 (10)°	T = 298 K
γ = 78.591 (12)°	Block, colourless
V = 787.4 (10) Å3	0.29 × 0.23 × 0.20 mm

Bruker SMART APEX CCD diffractometer	3795 independent reflections
Radiation source: fine-focus sealed tube	3322 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 8.34 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	k = −12→11
Tmin = 0.941, Tmax = 0.959	l = −13→13
7363 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H-atom parameters not refined
S = 1.05	w = 1/[σ2(Fo2) + (0.0559P)2 + 0.1486P] where P = (Fo2 + 2Fc2)/3
3795 reflections	(Δ/σ)max = 0.002
208 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. Absorption correction: SADABS (Sheldrick, 2004) was used for absorption correction. Rint was 0.0331 before and 0.0128 after correction. The ratio of minimum to maximum transmission is 0.8482. The λ/2 correction factor is 0.0015.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.

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	0.19222 (17)	0.19834 (14)	0.51794 (14)	0.0451 (3)
C2	0.01727 (17)	0.24186 (15)	0.62281 (14)	0.0467 (3)
C3	−0.1009 (2)	0.1554 (2)	0.65325 (17)	0.0602 (4)
H3	−0.0686	0.0659	0.6213	0.072*
C4	−0.2667 (2)	0.2042 (3)	0.7316 (2)	0.0766 (6)
H4	−0.3480	0.1474	0.7561	0.092*
C5	−0.3088 (2)	0.3386 (3)	0.7723 (2)	0.0799 (6)
H5	−0.4211	0.3726	0.8197	0.096*
C6	−0.03959 (18)	0.37357 (16)	0.67724 (15)	0.0498 (3)
C7	0.27666 (16)	0.35802 (14)	0.62977 (14)	0.0430 (3)
H7	0.3722	0.4092	0.5913	0.052*
C8	0.26430 (15)	0.28466 (13)	0.77829 (13)	0.0412 (3)
C9	0.2928 (2)	0.14162 (16)	0.80549 (17)	0.0562 (4)
H9	0.3126	0.0841	0.7334	0.067*
C10	0.2920 (3)	0.08234 (19)	0.9406 (2)	0.0701 (5)
H10	0.3106	−0.0146	0.9582	0.084*
C11	0.2641 (2)	0.1654 (2)	1.04781 (18)	0.0660 (4)
H11	0.2652	0.1252	1.1372	0.079*
C12	0.2347 (2)	0.3081 (2)	1.02200 (17)	0.0620 (4)
H12	0.2153	0.3650	1.0944	0.074*
C13	0.23370 (18)	0.36766 (16)	0.88894 (16)	0.0526 (3)
H13	0.2123	0.4646	0.8730	0.063*
C14	0.47645 (16)	0.24896 (14)	0.40084 (14)	0.0435 (3)
C15	0.4999 (2)	0.29060 (18)	0.25726 (16)	0.0576 (4)
H15	0.4095	0.3254	0.2351	0.069*
C16	0.6598 (2)	0.2800 (2)	0.14615 (18)	0.0723 (5)
H16	0.6762	0.3074	0.0489	0.087*
C17	0.7934 (2)	0.23006 (19)	0.1770 (2)	0.0689 (5)
H17	0.9002	0.2233	0.1013	0.083*
C18	0.7697 (2)	0.1902 (2)	0.3191 (2)	0.0736 (5)
H18	0.8609	0.1576	0.3406	0.088*
C19	0.6115 (2)	0.1978 (2)	0.43170 (19)	0.0666 (4)
H19	0.5963	0.1684	0.5283	0.080*
N1	0.31171 (14)	0.26429 (12)	0.51779 (12)	0.0452 (3)
N2	−0.19949 (17)	0.42352 (18)	0.74849 (15)	0.0673 (4)
O1	0.22485 (14)	0.11017 (12)	0.43317 (12)	0.0589 (3)
S1	0.09809 (5)	0.49046 (4)	0.64714 (4)	0.05549 (13)

	U11	U22	U33	U12	U13	U23
C1	0.0498 (7)	0.0485 (7)	0.0426 (6)	−0.0085 (5)	−0.0234 (6)	−0.0060 (5)
C2	0.0463 (7)	0.0579 (8)	0.0415 (6)	−0.0094 (6)	−0.0234 (5)	−0.0029 (5)
C3	0.0595 (9)	0.0792 (11)	0.0528 (8)	−0.0234 (8)	−0.0304 (7)	0.0010 (7)
C4	0.0540 (9)	0.1285 (18)	0.0571 (9)	−0.0349 (10)	−0.0282 (8)	0.0058 (10)
C5	0.0447 (9)	0.1375 (19)	0.0563 (9)	−0.0019 (10)	−0.0224 (7)	−0.0157 (11)
C6	0.0488 (7)	0.0625 (8)	0.0417 (6)	−0.0003 (6)	−0.0251 (6)	−0.0056 (6)
C7	0.0435 (6)	0.0461 (7)	0.0435 (6)	−0.0081 (5)	−0.0189 (5)	−0.0109 (5)
C8	0.0369 (6)	0.0487 (7)	0.0423 (6)	−0.0065 (5)	−0.0177 (5)	−0.0118 (5)
C9	0.0744 (10)	0.0499 (8)	0.0532 (8)	−0.0098 (7)	−0.0323 (7)	−0.0109 (6)
C10	0.0976 (13)	0.0576 (9)	0.0649 (10)	−0.0148 (9)	−0.0447 (10)	0.0030 (8)
C11	0.0705 (10)	0.0854 (12)	0.0470 (8)	−0.0160 (9)	−0.0290 (7)	−0.0011 (8)
C12	0.0624 (9)	0.0820 (11)	0.0492 (8)	−0.0037 (8)	−0.0266 (7)	−0.0246 (8)
C13	0.0561 (8)	0.0541 (8)	0.0553 (8)	−0.0011 (6)	−0.0282 (7)	−0.0200 (6)
C14	0.0448 (7)	0.0458 (6)	0.0415 (6)	−0.0055 (5)	−0.0183 (5)	−0.0090 (5)
C15	0.0584 (9)	0.0695 (9)	0.0472 (7)	−0.0113 (7)	−0.0256 (7)	0.0002 (7)
C16	0.0765 (11)	0.0902 (13)	0.0435 (8)	−0.0266 (10)	−0.0146 (8)	−0.0020 (8)
C17	0.0527 (9)	0.0664 (10)	0.0707 (11)	−0.0141 (7)	−0.0042 (8)	−0.0190 (8)
C18	0.0475 (8)	0.0818 (12)	0.0854 (13)	0.0007 (8)	−0.0265 (8)	−0.0082 (10)
C19	0.0529 (9)	0.0902 (12)	0.0555 (9)	−0.0032 (8)	−0.0271 (7)	0.0001 (8)
N1	0.0431 (6)	0.0556 (6)	0.0402 (5)	−0.0071 (5)	−0.0172 (4)	−0.0136 (5)
N2	0.0490 (7)	0.0977 (11)	0.0548 (7)	0.0103 (7)	−0.0262 (6)	−0.0176 (7)
O1	0.0654 (6)	0.0604 (6)	0.0578 (6)	−0.0134 (5)	−0.0254 (5)	−0.0196 (5)
S1	0.0646 (2)	0.0454 (2)	0.0607 (2)	0.00138 (16)	−0.03260 (19)	−0.00882 (15)

C1—O1	1.2220 (17)	C9—H9	0.9300
C1—N1	1.3653 (18)	C10—C11	1.371 (3)
C1—C2	1.491 (2)	C10—H10	0.9300
C2—C3	1.391 (2)	C11—C12	1.369 (3)
C2—C6	1.397 (2)	C11—H11	0.9300
C3—C4	1.381 (3)	C12—C13	1.381 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.373 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—C19	1.376 (2)
C5—N2	1.333 (3)	C14—C15	1.377 (2)
C5—H5	0.9300	C14—N1	1.4371 (18)
C6—N2	1.332 (2)	C15—C16	1.385 (2)
C6—S1	1.7511 (18)	C15—H15	0.9300
C7—N1	1.4654 (17)	C16—C17	1.362 (3)
C7—C8	1.522 (2)	C16—H16	0.9300
C7—S1	1.8230 (17)	C17—C18	1.359 (3)
C7—H7	0.9800	C17—H17	0.9300
C8—C9	1.374 (2)	C18—C19	1.380 (3)
C8—C13	1.3921 (19)	C18—H18	0.9300
C9—C10	1.393 (2)	C19—H19	0.9300
O1—C1—N1	122.08 (13)	C12—C11—C10	119.39 (15)
O1—C1—C2	120.66 (12)	C12—C11—H11	120.3
N1—C1—C2	117.23 (12)	C10—C11—H11	120.3
C3—C2—C6	117.43 (14)	C11—C12—C13	120.27 (14)
C3—C2—C1	118.63 (14)	C11—C12—H12	119.9
C6—C2—C1	123.37 (13)	C13—C12—H12	119.9
C4—C3—C2	119.06 (18)	C12—C13—C8	120.93 (15)
C4—C3—H3	120.5	C12—C13—H13	119.5
C2—C3—H3	120.5	C8—C13—H13	119.5
C5—C4—C3	118.40 (17)	C19—C14—C15	119.68 (14)
C5—C4—H4	120.8	C19—C14—N1	120.54 (13)
C3—C4—H4	120.8	C15—C14—N1	119.74 (13)
N2—C5—C4	124.37 (17)	C14—C15—C16	119.18 (15)
N2—C5—H5	117.8	C14—C15—H15	120.4
C4—C5—H5	117.8	C16—C15—H15	120.4
N2—C6—C2	123.93 (15)	C17—C16—C15	121.06 (17)
N2—C6—S1	114.61 (13)	C17—C16—H16	119.5
C2—C6—S1	121.38 (12)	C15—C16—H16	119.5
N1—C7—C8	115.03 (12)	C18—C17—C16	119.54 (16)
N1—C7—S1	111.09 (9)	C18—C17—H17	120.2
C8—C7—S1	112.49 (9)	C16—C17—H17	120.2
N1—C7—H7	105.8	C17—C18—C19	120.59 (17)
C8—C7—H7	105.8	C17—C18—H18	119.7
S1—C7—H7	105.8	C19—C18—H18	119.7
C9—C8—C13	118.39 (13)	C14—C19—C18	119.94 (16)
C9—C8—C7	123.51 (11)	C14—C19—H19	120.0
C13—C8—C7	117.95 (13)	C18—C19—H19	120.0
C8—C9—C10	120.29 (13)	C1—N1—C14	120.09 (11)
C8—C9—H9	119.9	C1—N1—C7	122.27 (11)
C10—C9—H9	119.9	C14—N1—C7	117.56 (11)
C11—C10—C9	120.73 (17)	C5—N2—C6	116.65 (17)
C11—C10—H10	119.6	C6—S1—C7	96.48 (9)
C9—C10—H10	119.6
O1—C1—C2—C3	18.1 (2)	C14—C15—C16—C17	−0.4 (3)
N1—C1—C2—C3	−164.00 (12)	C15—C16—C17—C18	−0.1 (3)
O1—C1—C2—C6	−152.95 (14)	C16—C17—C18—C19	1.1 (3)
N1—C1—C2—C6	24.91 (19)	C15—C14—C19—C18	0.8 (3)
C6—C2—C3—C4	1.5 (2)	N1—C14—C19—C18	−176.76 (16)
C1—C2—C3—C4	−170.08 (13)	C17—C18—C19—C14	−1.4 (3)
C2—C3—C4—C5	2.1 (2)	O1—C1—N1—C14	10.5 (2)
C3—C4—C5—N2	−3.9 (3)	C2—C1—N1—C14	−167.36 (11)
C3—C2—C6—N2	−4.0 (2)	O1—C1—N1—C7	−172.88 (13)
C1—C2—C6—N2	167.17 (13)	C2—C1—N1—C7	9.29 (18)
C3—C2—C6—S1	179.39 (10)	C19—C14—N1—C1	−122.82 (16)
C1—C2—C6—S1	−9.42 (18)	C15—C14—N1—C1	59.58 (19)
N1—C7—C8—C9	3.60 (18)	C19—C14—N1—C7	60.37 (19)
S1—C7—C8—C9	132.15 (13)	C15—C14—N1—C7	−117.22 (15)
N1—C7—C8—C13	179.04 (11)	C8—C7—N1—C1	77.79 (15)
S1—C7—C8—C13	−52.41 (14)	S1—C7—N1—C1	−51.45 (16)
C13—C8—C9—C10	−0.5 (2)	C8—C7—N1—C14	−105.48 (13)
C7—C8—C9—C10	174.93 (15)	S1—C7—N1—C14	125.27 (11)
C8—C9—C10—C11	−0.5 (3)	C4—C5—N2—C6	1.6 (3)
C9—C10—C11—C12	0.8 (3)	C2—C6—N2—C5	2.5 (2)
C10—C11—C12—C13	−0.2 (3)	S1—C6—N2—C5	179.27 (12)
C11—C12—C13—C8	−0.8 (2)	N2—C6—S1—C7	156.14 (11)
C9—C8—C13—C12	1.1 (2)	C2—C6—S1—C7	−26.97 (12)
C7—C8—C13—C12	−174.57 (13)	N1—C7—S1—C6	53.86 (10)
C19—C14—C15—C16	0.1 (2)	C8—C7—S1—C6	−76.72 (10)
N1—C14—C15—C16	177.69 (14)