3-(4-Methoxybenzyl)-1,5-benzo-thiazepin-4(5H)-one.

In the title compound, C17H15NO2S, the thia-zepine ring adopts a slightly distorted twist-boat conformation. The dihedral angle between the mean plane of the benzo-thia-zepin ring system and the benzene ring is 65.7 (1)°. In the crystal, pairs of N-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers, generating R2 (2) (8) ring motifs. These dimers are further linked by C-H⋯π and π-π inter-actions [inter-centroid distance between the benzene rings of the benzo-thia-zepine unit = 3.656 (3) Å] into a three-dimensional supra-molecular network.

Related literature

For background to the biology of thia­zepin derivatives and for a related structure, see: Bakthadoss et al. (2013 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H15NO2S

M = 297.36

Triclinic,

a = 7.678 (5) Å

b = 9.612 (5) Å

c = 10.860 (5) Å

α = 77.208 (5)°

β = 74.117 (4)°

γ = 81.522 (5)°

V = 748.5 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.23 × 0.21 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.951, T max = 0.968

18449 measured reflections

5363 independent reflections

3676 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.134

S = 1.05

5363 reflections

191 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP (Bruker, 2004 ▶); 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, 2012) ▶; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813009215/sj5315sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009215/sj5315Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009215/sj5315Isup3.cml

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

C17H15NO2S	Z = 2
Mr = 297.36	F(000) = 312
Triclinic, P1	Dx = 1.319 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.678 (5) Å	Cell parameters from 5471 reflections
b = 9.612 (5) Å	θ = 2.0–32.6°
c = 10.860 (5) Å	µ = 0.22 mm−1
α = 77.208 (5)°	T = 293 K
β = 74.117 (4)°	Block, colourless
γ = 81.522 (5)°	0.23 × 0.21 × 0.15 mm
V = 748.5 (7) Å3

Bruker APEXII CCD diffractometer	5363 independent reflections
Radiation source: fine-focus sealed tube	3676 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
Detector resolution: 10.0 pixels mm-1	θmax = 32.6°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −14→14
Tmin = 0.951, Tmax = 0.968	l = −15→16
18449 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.1157P] where P = (Fo2 + 2Fc2)/3
5363 reflections	(Δ/σ)max = 0.002
191 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 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
C1	0.42839 (17)	0.53284 (13)	0.19547 (13)	0.0389 (3)
H1	0.5174	0.5738	0.2152	0.047*
C2	0.18042 (19)	0.35576 (13)	0.34697 (13)	0.0404 (3)
C3	0.1350 (2)	0.29642 (16)	0.47950 (15)	0.0552 (4)
H3	0.2268	0.2590	0.5217	0.066*
C4	−0.0434 (3)	0.29249 (19)	0.54865 (16)	0.0639 (5)
H4	−0.0720	0.2511	0.6368	0.077*
C5	−0.1794 (2)	0.34965 (18)	0.48779 (16)	0.0595 (4)
H5	−0.3004	0.3466	0.5347	0.071*
C6	−0.1378 (2)	0.41157 (16)	0.35764 (14)	0.0475 (3)
H6	−0.2307	0.4514	0.3172	0.057*
C7	0.04227 (17)	0.41513 (13)	0.28606 (12)	0.0366 (3)
C8	0.19209 (16)	0.56421 (13)	0.07296 (12)	0.0344 (2)
C9	0.32623 (15)	0.61867 (13)	0.12345 (11)	0.0336 (2)
C10	0.34837 (18)	0.77722 (14)	0.07485 (14)	0.0415 (3)
H10A	0.3754	0.7968	−0.0196	0.050*
H10B	0.2336	0.8310	0.1066	0.050*
C11	0.49498 (17)	0.83050 (13)	0.11561 (13)	0.0377 (3)
C12	0.45462 (19)	0.90507 (15)	0.21596 (14)	0.0452 (3)
H12	0.3338	0.9228	0.2601	0.054*
C13	0.5907 (2)	0.95475 (16)	0.25307 (15)	0.0504 (3)
H13	0.5607	1.0052	0.3210	0.060*
C14	0.76966 (19)	0.92861 (14)	0.18852 (15)	0.0456 (3)
C15	0.81273 (19)	0.85446 (15)	0.08668 (16)	0.0497 (3)
H15	0.9335	0.8372	0.0423	0.060*
C16	0.67642 (19)	0.80638 (15)	0.05125 (15)	0.0462 (3)
H16	0.7066	0.7567	−0.0172	0.055*
C17	0.8784 (3)	1.0769 (2)	0.2951 (3)	0.0859 (7)
H17A	0.8026	1.1564	0.2609	0.129*
H17B	0.9907	1.1094	0.2953	0.129*
H17C	0.8171	1.0362	0.3825	0.129*
N1	0.07583 (14)	0.47009 (12)	0.15072 (10)	0.0391 (2)
H1A	0.0114	0.4382	0.1114	0.047*
O1	0.18656 (13)	0.60841 (11)	−0.04169 (9)	0.0456 (2)
O2	0.91500 (16)	0.97189 (13)	0.21607 (13)	0.0668 (3)
S1	0.41037 (5)	0.34901 (4)	0.25677 (4)	0.05008 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0361 (6)	0.0382 (6)	0.0460 (7)	−0.0061 (5)	−0.0172 (5)	−0.0053 (5)
C2	0.0500 (7)	0.0328 (6)	0.0419 (7)	−0.0089 (5)	−0.0177 (6)	−0.0033 (5)
C3	0.0772 (11)	0.0465 (8)	0.0470 (8)	−0.0166 (7)	−0.0288 (8)	0.0044 (6)
C4	0.0900 (13)	0.0610 (9)	0.0383 (8)	−0.0249 (9)	−0.0106 (8)	0.0002 (7)
C5	0.0627 (10)	0.0624 (9)	0.0476 (9)	−0.0190 (8)	0.0023 (7)	−0.0097 (7)
C6	0.0440 (7)	0.0525 (8)	0.0460 (8)	−0.0094 (6)	−0.0091 (6)	−0.0090 (6)
C7	0.0424 (6)	0.0363 (6)	0.0346 (6)	−0.0104 (5)	−0.0117 (5)	−0.0070 (5)
C8	0.0328 (6)	0.0381 (6)	0.0352 (6)	−0.0030 (4)	−0.0122 (5)	−0.0083 (5)
C9	0.0315 (5)	0.0364 (5)	0.0351 (6)	−0.0053 (4)	−0.0111 (5)	−0.0064 (4)
C10	0.0415 (7)	0.0381 (6)	0.0480 (7)	−0.0074 (5)	−0.0196 (6)	−0.0017 (5)
C11	0.0377 (6)	0.0320 (5)	0.0441 (7)	−0.0069 (5)	−0.0140 (5)	−0.0018 (5)
C12	0.0401 (7)	0.0446 (7)	0.0500 (8)	−0.0056 (5)	−0.0076 (6)	−0.0108 (6)
C13	0.0590 (9)	0.0453 (7)	0.0532 (8)	−0.0077 (6)	−0.0170 (7)	−0.0168 (6)
C14	0.0458 (7)	0.0337 (6)	0.0629 (9)	−0.0073 (5)	−0.0253 (6)	−0.0037 (6)
C15	0.0358 (7)	0.0471 (7)	0.0667 (10)	−0.0037 (5)	−0.0121 (6)	−0.0132 (7)
C16	0.0424 (7)	0.0462 (7)	0.0535 (8)	−0.0048 (5)	−0.0114 (6)	−0.0169 (6)
C17	0.0936 (15)	0.0580 (10)	0.138 (2)	−0.0058 (10)	−0.0690 (14)	−0.0361 (12)
N1	0.0399 (5)	0.0479 (6)	0.0349 (5)	−0.0135 (5)	−0.0146 (4)	−0.0064 (4)
O1	0.0453 (5)	0.0596 (6)	0.0358 (5)	−0.0154 (4)	−0.0168 (4)	−0.0019 (4)
O2	0.0591 (7)	0.0568 (6)	0.1027 (10)	−0.0091 (5)	−0.0422 (7)	−0.0231 (6)
S1	0.0448 (2)	0.03683 (18)	0.0684 (3)	0.00032 (13)	−0.02330 (17)	−0.00078 (15)

C1—C9	1.3292 (18)	C10—C11	1.5061 (18)
C1—S1	1.7565 (15)	C10—H10A	0.9700
C1—H1	0.9300	C10—H10B	0.9700
C2—C7	1.3881 (19)	C11—C12	1.3758 (19)
C2—C3	1.392 (2)	C11—C16	1.388 (2)
C2—S1	1.7688 (17)	C12—C13	1.395 (2)
C3—C4	1.372 (3)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.375 (2)
C4—C5	1.370 (3)	C13—H13	0.9300
C4—H4	0.9300	C14—O2	1.3721 (17)
C5—C6	1.375 (2)	C14—C15	1.386 (2)
C5—H5	0.9300	C15—C16	1.378 (2)
C6—C7	1.389 (2)	C15—H15	0.9300
C6—H6	0.9300	C16—H16	0.9300
C7—N1	1.4124 (17)	C17—O2	1.415 (2)
C8—O1	1.2337 (16)	C17—H17A	0.9600
C8—N1	1.3474 (16)	C17—H17B	0.9600
C8—C9	1.4935 (16)	C17—H17C	0.9600
C9—C10	1.5170 (18)	N1—H1A	0.8600
C9—C1—S1	125.87 (10)	C9—C10—H10B	108.6
C9—C1—H1	117.1	H10A—C10—H10B	107.6
S1—C1—H1	117.1	C12—C11—C16	117.91 (12)
C7—C2—C3	119.01 (14)	C12—C11—C10	121.68 (12)
C7—C2—S1	120.68 (11)	C16—C11—C10	120.41 (12)
C3—C2—S1	120.27 (12)	C11—C12—C13	121.51 (13)
C4—C3—C2	120.83 (15)	C11—C12—H12	119.2
C4—C3—H3	119.6	C13—C12—H12	119.2
C2—C3—H3	119.6	C14—C13—C12	119.54 (13)
C5—C4—C3	119.96 (15)	C14—C13—H13	120.2
C5—C4—H4	120.0	C12—C13—H13	120.2
C3—C4—H4	120.0	O2—C14—C13	124.88 (14)
C4—C5—C6	120.22 (16)	O2—C14—C15	115.39 (13)
C4—C5—H5	119.9	C13—C14—C15	119.73 (12)
C6—C5—H5	119.9	C16—C15—C14	119.91 (13)
C5—C6—C7	120.46 (15)	C16—C15—H15	120.0
C5—C6—H6	119.8	C14—C15—H15	120.0
C7—C6—H6	119.8	C15—C16—C11	121.40 (13)
C2—C7—C6	119.49 (13)	C15—C16—H16	119.3
C2—C7—N1	122.61 (12)	C11—C16—H16	119.3
C6—C7—N1	117.72 (12)	O2—C17—H17A	109.5
O1—C8—N1	119.75 (10)	O2—C17—H17B	109.5
O1—C8—C9	118.99 (11)	H17A—C17—H17B	109.5
N1—C8—C9	121.26 (11)	O2—C17—H17C	109.5
C1—C9—C8	122.57 (11)	H17A—C17—H17C	109.5
C1—C9—C10	122.99 (11)	H17B—C17—H17C	109.5
C8—C9—C10	114.20 (10)	C8—N1—C7	130.70 (10)
C11—C10—C9	114.61 (10)	C8—N1—H1A	114.6
C11—C10—H10A	108.6	C7—N1—H1A	114.6
C9—C10—H10A	108.6	C14—O2—C17	117.51 (14)
C11—C10—H10B	108.6	C1—S1—C2	99.41 (6)
C7—C2—C3—C4	1.9 (2)	C9—C10—C11—C16	78.58 (16)
S1—C2—C3—C4	−175.66 (12)	C16—C11—C12—C13	−0.3 (2)
C2—C3—C4—C5	−1.1 (2)	C10—C11—C12—C13	−179.73 (13)
C3—C4—C5—C6	−0.3 (3)	C11—C12—C13—C14	−0.2 (2)
C4—C5—C6—C7	0.9 (2)	C12—C13—C14—O2	180.00 (14)
C3—C2—C7—C6	−1.28 (18)	C12—C13—C14—C15	0.6 (2)
S1—C2—C7—C6	176.27 (10)	O2—C14—C15—C16	−179.96 (13)
C3—C2—C7—N1	−176.30 (11)	C13—C14—C15—C16	−0.5 (2)
S1—C2—C7—N1	1.25 (16)	C14—C15—C16—C11	0.0 (2)
C5—C6—C7—C2	−0.1 (2)	C12—C11—C16—C15	0.4 (2)
C5—C6—C7—N1	175.17 (12)	C10—C11—C16—C15	179.84 (13)
S1—C1—C9—C8	−6.64 (19)	O1—C8—N1—C7	−172.86 (12)
S1—C1—C9—C10	179.39 (10)	C9—C8—N1—C7	6.0 (2)
O1—C8—C9—C1	−134.74 (14)	C2—C7—N1—C8	−51.01 (19)
N1—C8—C9—C1	46.39 (18)	C6—C7—N1—C8	133.88 (14)
O1—C8—C9—C10	39.71 (16)	C13—C14—O2—C17	−14.9 (2)
N1—C8—C9—C10	−139.16 (12)	C15—C14—O2—C17	164.55 (16)
C1—C9—C10—C11	−0.45 (19)	C9—C1—S1—C2	−57.47 (14)
C8—C9—C10—C11	−174.88 (11)	C7—C2—S1—C1	58.98 (11)
C9—C10—C11—C12	−102.00 (15)	C3—C2—S1—C1	−123.50 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.02	2.860 (2)	167
C17—H17B···Cgii	0.96	2.96	3.561 (3)	122

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C3–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.02	2.860 (2)	167
C17—H17B⋯Cg ii	0.96	2.96	3.561 (3)	122

Symmetry codes: (i) ; (ii) .