Crystal structure of 4-benzyl-2H-benzo[b][1,4]thia-zin-3(4H)-one.

In the title compound, C15H13NOS, the thia-zine ring adopts a twisted boat conformation and the dihedral angle between the aromatic rings is 86.54 (4)°. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, resulting in chains along [010].

Related literature

For related structures and background to 1,4-benzo­thia­zine derivatives, see: Zerzouf et al. (2001 ▸); Sebbar et al. (2015 ▸).

Experimental

Crystal data

C15H13NOS

M = 255.32

Monoclinic,

a = 10.8711 (7) Å

b = 5.3815 (3) Å

c = 21.1997 (13) Å

β = 93.128 (1)°

V = 1238.39 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.25 mm−1

T = 150 K

0.31 × 0.19 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2015 ▸) T min = 0.88, T max = 0.96

22588 measured reflections

3318 independent reflections

2731 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.06

3318 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2015 ▸); cell refinement: SAINT (Bruker, 2015 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2015a ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b ▸); molecular graphics: DIAMOND (Brandenburg & Putz, 2012 ▸); software used to prepare material for publication: SHELXTL (Sheldrick, 2015b ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989015022276/hb7545sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015022276/hb7545Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015022276/hb7545Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015022276/hb7545fig1.tif

Perspective view of the mol­ecule with 50% probability ellipsoids.

Click here for additional data file.

b . DOI: 10.1107/S2056989015022276/hb7545fig2.tif

Packing viewed down the b axis. Inter­molecular C—H⋯O inter­actions are shown by dotted lines.

CCDC reference: 1438105

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

C15H13NOS	F(000) = 536
Mr = 255.32	Dx = 1.369 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.8711 (7) Å	Cell parameters from 9273 reflections
b = 5.3815 (3) Å	θ = 2.6–29.0°
c = 21.1997 (13) Å	µ = 0.25 mm−1
β = 93.128 (1)°	T = 150 K
V = 1238.39 (13) Å3	Block, colourless
Z = 4	0.31 × 0.19 × 0.15 mm

Bruker SMART APEX CCD diffractometer	3318 independent reflections
Radiation source: fine-focus sealed tube	2731 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 8.3333 pixels mm-1	θmax = 29.1°, θmin = 1.9°
φ and ω scans	h = −14→14
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −7→7
Tmin = 0.88, Tmax = 0.96	l = −28→28
22588 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0711P)2 + 0.0734P] where P = (Fo2 + 2Fc2)/3
3318 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at φ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in φ, collected at ω = −30.00 and 210.00°. The scan time was 20 sec/frame.

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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 − 0.99 Å). All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

	x	y	z	Uiso*/Ueq
S1	1.01122 (3)	0.51867 (6)	0.64271 (2)	0.02520 (11)
O1	0.82014 (8)	0.06255 (17)	0.72781 (4)	0.0263 (2)
N1	0.77044 (9)	0.22455 (18)	0.63087 (4)	0.0188 (2)
C1	0.78669 (10)	0.4044 (2)	0.58307 (5)	0.0183 (2)
C2	0.69629 (11)	0.4345 (2)	0.53375 (5)	0.0228 (2)
H2	0.6216	0.3430	0.5342	0.027*
C3	0.71505 (12)	0.5966 (2)	0.48439 (5)	0.0266 (3)
H3	0.6537	0.6136	0.4510	0.032*
C4	0.82274 (12)	0.7341 (2)	0.48348 (5)	0.0283 (3)
H4	0.8359	0.8435	0.4493	0.034*
C5	0.91096 (12)	0.7109 (3)	0.53267 (5)	0.0273 (3)
H5	0.9839	0.8080	0.5325	0.033*
C6	0.89443 (10)	0.5470 (2)	0.58242 (5)	0.0204 (2)
C7	0.90903 (11)	0.4571 (2)	0.70494 (5)	0.0202 (2)
H7A	0.9579	0.4299	0.7451	0.024*
H7B	0.8549	0.6026	0.7104	0.024*
C8	0.83135 (10)	0.2310 (2)	0.68959 (5)	0.0191 (2)
C9	0.68427 (11)	0.0192 (2)	0.61862 (6)	0.0206 (2)
H9A	0.7166	−0.1296	0.6415	0.025*
H9B	0.6814	−0.0193	0.5729	0.025*
C10	0.55414 (10)	0.0666 (2)	0.63773 (5)	0.0185 (2)
C11	0.52211 (11)	0.2662 (2)	0.67490 (5)	0.0239 (3)
H11	0.5828	0.3854	0.6879	0.029*
C12	0.40231 (12)	0.2935 (3)	0.69330 (5)	0.0290 (3)
H12	0.3813	0.4312	0.7186	0.035*
C13	0.31340 (12)	0.1201 (3)	0.67478 (6)	0.0302 (3)
H13	0.2314	0.1387	0.6874	0.036*
C14	0.34421 (12)	−0.0800 (3)	0.63797 (7)	0.0319 (3)
H14	0.2835	−0.1998	0.6255	0.038*
C15	0.46353 (11)	−0.1061 (2)	0.61924 (6)	0.0261 (3)
H15	0.4839	−0.2430	0.5935	0.031*

	U11	U22	U33	U12	U13	U23
S1	0.01580 (17)	0.0344 (2)	0.02528 (17)	−0.00305 (11)	−0.00034 (12)	0.00452 (11)
O1	0.0243 (4)	0.0259 (5)	0.0282 (4)	−0.0015 (4)	−0.0014 (3)	0.0087 (3)
N1	0.0177 (4)	0.0169 (5)	0.0215 (4)	−0.0014 (4)	−0.0006 (3)	−0.0006 (3)
C1	0.0192 (5)	0.0181 (5)	0.0178 (5)	0.0024 (4)	0.0019 (4)	−0.0025 (4)
C2	0.0227 (6)	0.0244 (6)	0.0210 (5)	−0.0001 (5)	−0.0022 (4)	−0.0040 (4)
C3	0.0296 (6)	0.0309 (7)	0.0189 (5)	0.0040 (5)	−0.0033 (5)	−0.0025 (5)
C4	0.0343 (7)	0.0302 (7)	0.0209 (5)	0.0020 (5)	0.0051 (5)	0.0054 (5)
C5	0.0243 (6)	0.0318 (7)	0.0263 (6)	−0.0026 (5)	0.0060 (5)	0.0039 (5)
C6	0.0171 (5)	0.0245 (6)	0.0198 (5)	0.0022 (4)	0.0019 (4)	−0.0011 (4)
C7	0.0200 (5)	0.0219 (6)	0.0186 (5)	−0.0010 (4)	−0.0006 (4)	0.0009 (4)
C8	0.0157 (5)	0.0195 (6)	0.0220 (5)	0.0034 (4)	0.0011 (4)	0.0006 (4)
C9	0.0195 (6)	0.0145 (5)	0.0276 (6)	−0.0002 (4)	0.0003 (4)	−0.0032 (4)
C10	0.0187 (5)	0.0167 (5)	0.0200 (5)	0.0008 (4)	−0.0010 (4)	0.0021 (4)
C11	0.0239 (6)	0.0234 (6)	0.0242 (5)	0.0017 (5)	−0.0014 (4)	−0.0022 (4)
C12	0.0302 (7)	0.0345 (7)	0.0228 (5)	0.0097 (6)	0.0050 (5)	−0.0008 (5)
C13	0.0218 (6)	0.0410 (8)	0.0283 (6)	0.0048 (5)	0.0055 (5)	0.0115 (6)
C14	0.0218 (6)	0.0306 (7)	0.0430 (7)	−0.0051 (5)	−0.0014 (5)	0.0061 (6)
C15	0.0236 (6)	0.0196 (6)	0.0349 (6)	−0.0012 (5)	−0.0004 (5)	−0.0023 (5)

S1—C6	1.7583 (11)	C7—H7A	0.9900
S1—C7	1.8013 (12)	C7—H7B	0.9900
O1—C8	1.2262 (14)	C9—C10	1.5144 (16)
N1—C8	1.3781 (13)	C9—H9A	0.9900
N1—C1	1.4191 (14)	C9—H9B	0.9900
N1—C9	1.4628 (14)	C10—C11	1.3880 (16)
C1—C6	1.4012 (16)	C10—C15	1.3947 (16)
C1—C2	1.4047 (15)	C11—C12	1.3876 (17)
C2—C3	1.3860 (18)	C11—H11	0.9500
C2—H2	0.9500	C12—C13	1.3848 (19)
C3—C4	1.3859 (19)	C12—H12	0.9500
C3—H3	0.9500	C13—C14	1.382 (2)
C4—C5	1.3833 (16)	C13—H13	0.9500
C4—H4	0.9500	C14—C15	1.3843 (18)
C5—C6	1.3940 (17)	C14—H14	0.9500
C5—H5	0.9500	C15—H15	0.9500
C7—C8	1.5066 (16)
C6—S1—C7	95.66 (5)	O1—C8—N1	121.21 (10)
C8—N1—C1	123.74 (9)	O1—C8—C7	121.93 (10)
C8—N1—C9	116.79 (9)	N1—C8—C7	116.84 (9)
C1—N1—C9	119.46 (9)	N1—C9—C10	115.07 (9)
C6—C1—C2	118.72 (10)	N1—C9—H9A	108.5
C6—C1—N1	121.15 (9)	C10—C9—H9A	108.5
C2—C1—N1	120.07 (10)	N1—C9—H9B	108.5
C3—C2—C1	120.60 (11)	C10—C9—H9B	108.5
C3—C2—H2	119.7	H9A—C9—H9B	107.5
C1—C2—H2	119.7	C11—C10—C15	118.70 (11)
C4—C3—C2	120.38 (11)	C11—C10—C9	123.32 (10)
C4—C3—H3	119.8	C15—C10—C9	117.92 (10)
C2—C3—H3	119.8	C12—C11—C10	120.65 (12)
C5—C4—C3	119.52 (11)	C12—C11—H11	119.7
C5—C4—H4	120.2	C10—C11—H11	119.7
C3—C4—H4	120.2	C13—C12—C11	120.02 (12)
C4—C5—C6	121.00 (12)	C13—C12—H12	120.0
C4—C5—H5	119.5	C11—C12—H12	120.0
C6—C5—H5	119.5	C14—C13—C12	119.89 (12)
C5—C6—C1	119.76 (10)	C14—C13—H13	120.1
C5—C6—S1	119.15 (9)	C12—C13—H13	120.1
C1—C6—S1	121.08 (9)	C13—C14—C15	120.04 (12)
C8—C7—S1	110.56 (8)	C13—C14—H14	120.0
C8—C7—H7A	109.5	C15—C14—H14	120.0
S1—C7—H7A	109.5	C14—C15—C10	120.69 (12)
C8—C7—H7B	109.5	C14—C15—H15	119.7
S1—C7—H7B	109.5	C10—C15—H15	119.7
H7A—C7—H7B	108.1
C8—N1—C1—C6	23.43 (16)	C1—N1—C8—O1	−175.23 (10)
C9—N1—C1—C6	−156.89 (11)	C9—N1—C8—O1	5.09 (15)
C8—N1—C1—C2	−159.32 (11)	C1—N1—C8—C7	6.40 (15)
C9—N1—C1—C2	20.36 (15)	C9—N1—C8—C7	−173.29 (10)
C6—C1—C2—C3	1.99 (17)	S1—C7—C8—O1	131.04 (10)
N1—C1—C2—C3	−175.32 (11)	S1—C7—C8—N1	−50.60 (12)
C1—C2—C3—C4	−0.93 (19)	C8—N1—C9—C10	88.08 (12)
C2—C3—C4—C5	−0.81 (19)	C1—N1—C9—C10	−91.62 (12)
C3—C4—C5—C6	1.48 (19)	N1—C9—C10—C11	−12.01 (16)
C4—C5—C6—C1	−0.40 (19)	N1—C9—C10—C15	170.98 (10)
C4—C5—C6—S1	178.35 (10)	C15—C10—C11—C12	0.00 (17)
C2—C1—C6—C5	−1.33 (17)	C9—C10—C11—C12	−176.99 (11)
N1—C1—C6—C5	175.96 (11)	C10—C11—C12—C13	0.24 (18)
C2—C1—C6—S1	179.95 (9)	C11—C12—C13—C14	0.01 (18)
N1—C1—C6—S1	−2.77 (15)	C12—C13—C14—C15	−0.51 (19)
C7—S1—C6—C5	147.46 (11)	C13—C14—C15—C10	0.75 (19)
C7—S1—C6—C1	−33.80 (10)	C11—C10—C15—C14	−0.49 (18)
C6—S1—C7—C8	57.87 (9)	C9—C10—C15—C14	176.66 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O1i	0.99	2.55	3.2504 (14)	128
C7—H7B···O1ii	0.99	2.53	3.4403 (15)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯O1i	0.99	2.55	3.2504 (14)	128
C7—H7B⋯O1ii	0.99	2.53	3.4403 (15)	152

Symmetry codes: (i) ; (ii) .