(Z)-3-Benzyl-1,5-benzothia-zepin-4(5H)-one.

In the crystal structure of the title compound, C(16)H(13)NOS, mol-ecules are linked into cyclic centrosymmetric R(2) (2)(8) dimers via pairs of N-H⋯O hydrogen bonds. The seven-membered ring adopts a boat conformation.

Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000 ▶); Rajsner et al. (1971 ▶); Metys et al. (1965 ▶). For conformations of thia­zepin derivatives, see: Huang et al. (2011 ▶). For a related structure, see: Sabari et al. (2012 ▶).For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C16H13NOS

M = 267.33

Monoclinic,

a = 9.3409 (6) Å

b = 11.7876 (7) Å

c = 11.8310 (6) Å

β = 94.727 (3)°

V = 1298.24 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.24 mm−1

T = 293 K

0.32 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.980, T max = 0.990

11696 measured reflections

3220 independent reflections

2700 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.100

S = 1.03

3220 reflections

224 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812029054/bt5942sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812029054/bt5942Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812029054/bt5942Isup3.cml

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

C16H13NOS	F(000) = 560
Mr = 267.33	Dx = 1.368 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8725 reflections
a = 9.3409 (6) Å	θ = 2.8–29.1°
b = 11.7876 (7) Å	µ = 0.24 mm−1
c = 11.8310 (6) Å	T = 293 K
β = 94.727 (3)°	Monoclinic, colourless
V = 1298.24 (13) Å3	0.32 × 0.20 × 0.10 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	3220 independent reflections
Radiation source: fine-focus sealed tube	2700 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
Detector resolution: 15.9948 pixels mm-1	θmax = 28.3°, θmin = 2.2°
ω and φ scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2008)	k = −12→15
Tmin = 0.980, Tmax = 0.990	l = −15→15
11696 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3853P] where P = (Fo2 + 2Fc2)/3
3220 reflections	(Δ/σ)max = 0.001
224 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

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
H10A	0.9319 (19)	0.4199 (16)	1.0576 (15)	0.054 (5)*
H14	1.158 (2)	0.0216 (19)	1.2706 (18)	0.071 (6)*
H13	1.253 (3)	0.210 (2)	1.287 (2)	0.090 (7)*
H2	0.520 (2)	0.0349 (17)	0.7510 (18)	0.067 (6)*
H4	0.264 (2)	0.0652 (19)	1.0082 (18)	0.075 (6)*
H3	0.341 (2)	−0.0401 (19)	0.8584 (18)	0.078 (6)*
H5	0.367 (2)	0.2445 (15)	1.0477 (16)	0.051 (5)*
H9	0.906 (2)	0.2452 (13)	0.8225 (15)	0.047 (4)*
H12	1.152 (2)	0.3537 (18)	1.1720 (16)	0.066 (6)*
H16	0.8605 (18)	0.1324 (14)	1.0263 (14)	0.048 (4)*
H15	0.960 (2)	−0.0149 (19)	1.1441 (18)	0.075 (6)*
H	0.4802 (19)	0.4003 (15)	0.9656 (14)	0.050 (5)*
H10B	1.0195 (19)	0.3709 (15)	0.9641 (15)	0.053 (5)*
S1	0.67169 (4)	0.23482 (4)	0.74334 (3)	0.04629 (13)
O1	0.69525 (11)	0.49768 (9)	1.00015 (11)	0.0515 (3)
N1	0.54541 (12)	0.35755 (9)	0.94400 (10)	0.0376 (3)
C9	0.81284 (15)	0.27217 (12)	0.84256 (12)	0.0377 (3)
C1	0.54547 (14)	0.18101 (11)	0.83286 (11)	0.0361 (3)
C8	0.80771 (13)	0.33382 (10)	0.93653 (11)	0.0326 (3)
C7	0.67881 (14)	0.40033 (11)	0.96316 (11)	0.0345 (3)
C10	0.94322 (15)	0.35387 (12)	1.01201 (13)	0.0397 (3)
C6	0.49997 (14)	0.24447 (10)	0.92206 (11)	0.0332 (3)
C11	0.99742 (13)	0.25642 (11)	1.08739 (11)	0.0335 (3)
C16	0.94145 (15)	0.14763 (12)	1.08123 (12)	0.0396 (3)
C12	1.11413 (16)	0.27689 (16)	1.16571 (13)	0.0490 (4)
C5	0.39623 (16)	0.20069 (14)	0.98728 (14)	0.0448 (3)
C14	1.11727 (19)	0.08314 (19)	1.22626 (15)	0.0599 (5)
C13	1.17296 (18)	0.1913 (2)	1.23380 (15)	0.0628 (5)
C2	0.48567 (18)	0.07488 (14)	0.80956 (15)	0.0511 (4)
C15	1.00050 (19)	0.06142 (15)	1.15013 (14)	0.0508 (4)
C4	0.33594 (18)	0.09600 (16)	0.96179 (17)	0.0568 (4)
C3	0.37969 (19)	0.03362 (15)	0.87283 (18)	0.0613 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0532 (2)	0.0562 (2)	0.02983 (18)	−0.00076 (17)	0.00540 (15)	−0.00396 (14)
O1	0.0427 (6)	0.0312 (5)	0.0809 (8)	0.0002 (4)	0.0071 (5)	−0.0154 (5)
N1	0.0322 (6)	0.0297 (5)	0.0512 (7)	0.0043 (4)	0.0054 (5)	−0.0075 (5)
C9	0.0372 (7)	0.0390 (7)	0.0381 (7)	0.0021 (5)	0.0096 (5)	0.0012 (5)
C1	0.0350 (6)	0.0356 (7)	0.0370 (6)	0.0033 (5)	−0.0019 (5)	−0.0029 (5)
C8	0.0327 (6)	0.0275 (6)	0.0382 (6)	−0.0004 (5)	0.0067 (5)	0.0038 (5)
C7	0.0363 (6)	0.0280 (6)	0.0396 (6)	0.0018 (5)	0.0054 (5)	−0.0013 (5)
C10	0.0339 (7)	0.0322 (7)	0.0530 (8)	−0.0054 (5)	0.0037 (6)	−0.0020 (6)
C6	0.0301 (6)	0.0311 (6)	0.0377 (6)	0.0021 (5)	−0.0018 (5)	−0.0018 (5)
C11	0.0258 (6)	0.0411 (7)	0.0340 (6)	−0.0021 (5)	0.0057 (5)	−0.0062 (5)
C16	0.0374 (7)	0.0402 (7)	0.0403 (7)	−0.0027 (6)	−0.0011 (5)	0.0001 (6)
C12	0.0338 (7)	0.0670 (10)	0.0457 (8)	−0.0105 (7)	0.0010 (6)	−0.0089 (7)
C5	0.0367 (7)	0.0492 (8)	0.0489 (8)	−0.0044 (6)	0.0063 (6)	−0.0045 (7)
C14	0.0478 (9)	0.0839 (13)	0.0477 (9)	0.0169 (9)	0.0033 (7)	0.0187 (9)
C13	0.0374 (8)	0.1029 (16)	0.0461 (9)	−0.0014 (9)	−0.0081 (7)	0.0013 (9)
C2	0.0507 (9)	0.0421 (8)	0.0593 (9)	0.0009 (7)	−0.0025 (7)	−0.0175 (7)
C15	0.0534 (9)	0.0482 (9)	0.0509 (8)	0.0051 (7)	0.0045 (7)	0.0096 (7)
C4	0.0458 (9)	0.0543 (10)	0.0705 (11)	−0.0141 (7)	0.0066 (8)	0.0015 (8)
C3	0.0529 (10)	0.0412 (9)	0.0888 (13)	−0.0142 (7)	−0.0001 (9)	−0.0104 (9)

S1—C9	1.7479 (15)	C11—C12	1.392 (2)
S1—C1	1.7663 (14)	C16—C15	1.388 (2)
O1—C7	1.2332 (16)	C16—H16	0.972 (17)
N1—C7	1.3460 (17)	C12—C13	1.377 (3)
N1—C6	1.4165 (16)	C12—H12	0.97 (2)
N1—H	0.846 (18)	C5—C4	1.379 (2)
C9—C8	1.3324 (19)	C5—H5	0.942 (19)
C9—H9	0.976 (18)	C14—C13	1.377 (3)
C1—C2	1.388 (2)	C14—C15	1.380 (3)
C1—C6	1.3885 (18)	C14—H14	0.96 (2)
C8—C7	1.4920 (17)	C13—H13	0.96 (3)
C8—C10	1.5064 (19)	C2—C3	1.378 (3)
C10—C11	1.515 (2)	C2—H2	0.92 (2)
C10—H10A	0.958 (19)	C15—H15	0.98 (2)
C10—H10B	0.968 (18)	C4—C3	1.373 (3)
C6—C5	1.387 (2)	C4—H4	0.97 (2)
C11—C16	1.3845 (19)	C3—H3	0.95 (2)
C9—S1—C1	101.05 (6)	C11—C16—C15	121.13 (14)
C7—N1—C6	129.99 (11)	C11—C16—H16	118.4 (10)
C7—N1—H	114.0 (12)	C15—C16—H16	120.4 (10)
C6—N1—H	113.8 (12)	C13—C12—C11	121.01 (17)
C8—C9—S1	128.37 (11)	C13—C12—H12	120.7 (12)
C8—C9—H9	118.4 (10)	C11—C12—H12	118.2 (12)
S1—C9—H9	113.2 (10)	C4—C5—C6	120.17 (15)
C2—C1—C6	119.54 (13)	C4—C5—H5	121.1 (11)
C2—C1—S1	118.81 (11)	C6—C5—H5	118.7 (11)
C6—C1—S1	121.57 (10)	C13—C14—C15	119.21 (16)
C9—C8—C7	123.22 (12)	C13—C14—H14	122.2 (13)
C9—C8—C10	119.61 (12)	C15—C14—H14	118.5 (13)
C7—C8—C10	116.46 (12)	C14—C13—C12	120.67 (16)
O1—C7—N1	119.66 (12)	C14—C13—H13	121.2 (15)
O1—C7—C8	119.00 (12)	C12—C13—H13	118.1 (15)
N1—C7—C8	121.30 (11)	C3—C2—C1	120.36 (15)
C8—C10—C11	116.97 (11)	C3—C2—H2	122.7 (13)
C8—C10—H10A	109.6 (11)	C1—C2—H2	117.0 (13)
C11—C10—H10A	109.4 (11)	C14—C15—C16	120.12 (17)
C8—C10—H10B	107.9 (10)	C14—C15—H15	120.0 (12)
C11—C10—H10B	106.0 (11)	C16—C15—H15	119.9 (13)
H10A—C10—H10B	106.3 (15)	C3—C4—C5	120.30 (16)
C5—C6—C1	119.61 (13)	C3—C4—H4	119.7 (13)
C5—C6—N1	117.44 (12)	C5—C4—H4	120.0 (13)
C1—C6—N1	122.71 (12)	C4—C3—C2	119.98 (16)
C16—C11—C12	117.84 (14)	C4—C3—H3	119.7 (13)
C16—C11—C10	124.38 (12)	C2—C3—H3	120.2 (13)
C12—C11—C10	117.75 (13)
C1—S1—C9—C8	−49.95 (14)	C7—N1—C6—C1	−56.6 (2)
C9—S1—C1—C2	−128.63 (12)	C8—C10—C11—C16	8.3 (2)
C9—S1—C1—C6	54.52 (12)	C8—C10—C11—C12	−173.77 (12)
S1—C9—C8—C7	−11.3 (2)	C12—C11—C16—C15	−0.6 (2)
S1—C9—C8—C10	178.70 (10)	C10—C11—C16—C15	177.38 (14)
C6—N1—C7—O1	−167.26 (14)	C16—C11—C12—C13	0.8 (2)
C6—N1—C7—C8	15.0 (2)	C10—C11—C12—C13	−177.31 (14)
C9—C8—C7—O1	−135.97 (15)	C1—C6—C5—C4	−1.7 (2)
C10—C8—C7—O1	34.35 (18)	N1—C6—C5—C4	172.74 (14)
C9—C8—C7—N1	41.8 (2)	C15—C14—C13—C12	−0.6 (3)
C10—C8—C7—N1	−147.91 (13)	C11—C12—C13—C14	−0.2 (3)
C9—C8—C10—C11	−76.59 (17)	C6—C1—C2—C3	1.4 (2)
C7—C8—C10—C11	112.72 (14)	S1—C1—C2—C3	−175.52 (14)
C2—C1—C6—C5	0.5 (2)	C13—C14—C15—C16	0.8 (3)
S1—C1—C6—C5	177.32 (11)	C11—C16—C15—C14	−0.2 (2)
C2—C1—C6—N1	−173.63 (13)	C6—C5—C4—C3	1.0 (3)
S1—C1—C6—N1	3.20 (18)	C5—C4—C3—C2	0.9 (3)
C7—N1—C6—C5	129.13 (16)	C1—C2—C3—C4	−2.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H···O1i	0.847 (18)	2.098 (19)	2.9407 (15)	173.1 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H⋯O1i	0.847 (18)	2.098 (19)	2.9407 (15)	173.1 (16)

Symmetry code: (i) .