(Z)-3-(3,4-Di-meth-oxy-benz-yl)-1,5-benzo-thia-zepin-4(5H)-one.

In the title compound, C18H17NO3S, 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 60.3 (1)°. In the crystal, mol-ecules are linked by two pairs of inversion-related N-H⋯O and C-H⋯O hydrogen bonds, generating alternating R 2 (2)(8) and R 2 (2)(6) ring motifs, respectively, in a zigzag supra-molecular chain that runs along the c axis. These chains stack along the a axis via S⋯C [3.424 (2) Å] contacts. A three-dimensional supra-molecular network is consolidated by C-H⋯π and π-π inter-actions [inter-centroid distance between di-meth-oxy-benzene rings = 3.815 (1) Å]. The crystal studied was a non-merohedral twin, with a refined value of the minor twin fraction of 0.2477 (6) .

Related literature

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

Experimental

Crystal data

C18H17NO3S

M = 327.39

Orthorhombic,

a = 19.966 (4) Å

b = 10.355 (2) Å

c = 15.536 (3) Å

V = 3212.0 (11) Å3

Z = 8

Mo Kα radiation

μ = 0.22 mm−1

T = 293 K

0.35 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (TWINABS; Sheldrick, 1997 ▶) T min = 0.927, T max = 0.968

13227 measured reflections

13227 independent reflections

8413 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.175

S = 1.02

13227 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.25 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/S1600536813009598/tk5214sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813009598/tk5214Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813009598/tk5214Isup3.cml

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

C18H17NO3S	F(000) = 1376
Mr = 327.39	Dx = 1.354 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2790 reflections
a = 19.966 (4) Å	θ = 2.2–24.9°
b = 10.355 (2) Å	µ = 0.22 mm−1
c = 15.536 (3) Å	T = 293 K
V = 3212.0 (11) Å3	Block, colourless
Z = 8	0.35 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	13227 independent reflections
Radiation source: fine-focus sealed tube	8413 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.066
Detector resolution: 10.0 pixels mm-1	θmax = 24.9°, θmin = 2.2°
ω scans	h = −23→23
Absorption correction: multi-scan (TWINABS; Sheldrick, 1997)	k = −12→9
Tmin = 0.927, Tmax = 0.968	l = −18→18
13227 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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.175	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0582P)2] where P = (Fo2 + 2Fc2)/3
13227 reflections	(Δ/σ)max = 0.001
211 parameters	Δρmax = 0.25 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
C2	0.21158 (10)	0.01584 (18)	1.02679 (11)	0.0320 (5)
C3	0.26554 (10)	0.0619 (2)	1.07376 (13)	0.0401 (5)
H3	0.3072	0.0225	1.0683	0.048*
C4	0.25791 (10)	0.1650 (2)	1.12822 (13)	0.0434 (6)
H4	0.2939	0.1935	1.1611	0.052*
C5	0.19688 (11)	0.2264 (2)	1.13416 (12)	0.0405 (5)
H5	0.1921	0.2978	1.1700	0.049*
C6	0.14302 (10)	0.18270 (19)	1.08740 (11)	0.0339 (5)
H6	0.1020	0.2249	1.0913	0.041*
C7	0.14978 (9)	0.07580 (18)	1.03449 (10)	0.0265 (4)
C8	0.07914 (10)	−0.00895 (17)	0.91369 (11)	0.0300 (5)
C9	0.13353 (9)	−0.00907 (17)	0.84820 (11)	0.0277 (5)
C1	0.19328 (11)	−0.05969 (19)	0.86307 (11)	0.0359 (5)
H1	0.2230	−0.0622	0.8170	0.043*
C10	0.11450 (10)	0.04089 (18)	0.76116 (11)	0.0332 (5)
H10A	0.0735	−0.0016	0.7432	0.040*
H10B	0.1493	0.0170	0.7206	0.040*
C11	0.10408 (8)	0.18544 (17)	0.75624 (10)	0.0267 (4)
C12	0.12408 (10)	0.2698 (2)	0.81859 (11)	0.0369 (5)
H12	0.1440	0.2384	0.8685	0.044*
C13	0.11523 (10)	0.4015 (2)	0.80865 (12)	0.0406 (5)
H13	0.1286	0.4574	0.8522	0.049*
C14	0.08704 (10)	0.45013 (18)	0.73534 (12)	0.0345 (5)
C15	0.06728 (9)	0.36546 (19)	0.67025 (11)	0.0305 (5)
C16	0.07503 (9)	0.23488 (19)	0.68158 (10)	0.0298 (5)
H16	0.0607	0.1785	0.6388	0.036*
C18	0.02274 (13)	0.3361 (2)	0.52964 (13)	0.0661 (8)
H18A	0.0616	0.2902	0.5099	0.099*
H18B	0.0042	0.3852	0.4830	0.099*
H18C	−0.0100	0.2756	0.5502	0.099*
C17	0.08134 (13)	0.6638 (2)	0.78994 (14)	0.0715 (8)
H17A	0.0536	0.6325	0.8359	0.107*
H17B	0.0665	0.7483	0.7730	0.107*
H17C	0.1270	0.6684	0.8091	0.107*
N1	0.09093 (8)	0.02648 (15)	0.99504 (9)	0.0325 (4)
H1A	0.0573	0.0180	1.0291	0.039*
O1	0.02201 (7)	−0.04165 (14)	0.89186 (8)	0.0423 (4)
O3	0.04118 (7)	0.42072 (13)	0.59744 (8)	0.0462 (4)
O2	0.07680 (8)	0.57865 (13)	0.71876 (9)	0.0498 (4)
S1	0.22192 (3)	−0.12256 (6)	0.96130 (3)	0.04692 (18)

	U11	U22	U33	U12	U13	U23
C2	0.0340 (13)	0.0353 (12)	0.0267 (10)	0.0018 (10)	−0.0032 (9)	0.0069 (9)
C3	0.0285 (13)	0.0482 (15)	0.0437 (12)	0.0032 (10)	−0.0051 (9)	0.0068 (11)
C4	0.0369 (15)	0.0530 (15)	0.0404 (12)	−0.0140 (12)	−0.0120 (10)	0.0064 (11)
C5	0.0447 (14)	0.0402 (13)	0.0366 (11)	−0.0090 (11)	−0.0044 (10)	−0.0018 (10)
C6	0.0347 (13)	0.0359 (13)	0.0311 (10)	−0.0005 (10)	0.0000 (9)	0.0014 (9)
C7	0.0256 (12)	0.0326 (12)	0.0214 (9)	−0.0028 (9)	−0.0011 (8)	0.0067 (9)
C8	0.0302 (13)	0.0278 (12)	0.0320 (10)	0.0017 (9)	−0.0025 (9)	0.0044 (9)
C9	0.0310 (12)	0.0249 (11)	0.0271 (9)	0.0008 (9)	−0.0016 (8)	−0.0015 (8)
C1	0.0391 (14)	0.0386 (13)	0.0300 (10)	0.0034 (10)	0.0048 (9)	−0.0031 (9)
C10	0.0394 (13)	0.0351 (12)	0.0252 (9)	−0.0004 (9)	0.0006 (8)	−0.0022 (9)
C11	0.0263 (12)	0.0297 (11)	0.0242 (9)	−0.0046 (9)	0.0029 (8)	0.0008 (9)
C12	0.0463 (14)	0.0395 (13)	0.0248 (10)	−0.0052 (11)	−0.0030 (9)	−0.0008 (9)
C13	0.0524 (15)	0.0357 (14)	0.0336 (11)	−0.0129 (11)	0.0002 (10)	−0.0083 (10)
C14	0.0406 (14)	0.0246 (12)	0.0384 (11)	−0.0057 (9)	0.0126 (10)	−0.0006 (10)
C15	0.0324 (13)	0.0324 (12)	0.0265 (10)	0.0009 (9)	0.0052 (8)	0.0046 (9)
C16	0.0319 (13)	0.0310 (12)	0.0263 (10)	−0.0039 (9)	0.0006 (8)	−0.0034 (9)
C18	0.111 (2)	0.0510 (16)	0.0358 (13)	0.0186 (15)	−0.0196 (13)	−0.0014 (11)
C17	0.118 (2)	0.0342 (15)	0.0621 (16)	−0.0121 (15)	0.0208 (15)	−0.0165 (13)
N1	0.0229 (10)	0.0474 (11)	0.0273 (8)	−0.0062 (8)	0.0031 (7)	0.0024 (8)
O1	0.0294 (9)	0.0628 (10)	0.0346 (7)	−0.0108 (7)	−0.0031 (6)	−0.0053 (7)
O3	0.0675 (11)	0.0373 (9)	0.0338 (8)	0.0099 (7)	−0.0051 (7)	0.0047 (7)
O2	0.0797 (12)	0.0244 (8)	0.0452 (8)	−0.0014 (8)	0.0113 (8)	−0.0036 (7)
S1	0.0543 (4)	0.0454 (4)	0.0411 (3)	0.0223 (3)	−0.0086 (3)	0.0000 (3)

C2—C3	1.386 (3)	C10—H10B	0.9700
C2—C7	1.386 (2)	C11—C12	1.364 (2)
C2—S1	1.770 (2)	C11—C16	1.394 (2)
C3—C4	1.371 (3)	C12—C13	1.383 (3)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.377 (3)	C13—C14	1.367 (3)
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.374 (3)	C14—O2	1.371 (2)
C5—H5	0.9300	C14—C15	1.395 (3)
C6—C7	1.385 (3)	C15—O3	1.370 (2)
C6—H6	0.9300	C15—C16	1.372 (3)
C7—N1	1.420 (2)	C16—H16	0.9300
C8—O1	1.237 (2)	C18—O3	1.419 (2)
C8—N1	1.337 (2)	C18—H18A	0.9600
C8—C9	1.488 (3)	C18—H18B	0.9600
C9—C1	1.323 (3)	C18—H18C	0.9600
C9—C10	1.497 (2)	C17—O2	1.417 (2)
C1—S1	1.7549 (19)	C17—H17A	0.9600
C1—H1	0.9300	C17—H17B	0.9600
C10—C11	1.513 (2)	C17—H17C	0.9600
C10—H10A	0.9700	N1—H1A	0.8600
C3—C2—C7	119.50 (18)	C16—C11—C10	117.55 (16)
C3—C2—S1	119.38 (16)	C11—C12—C13	120.97 (18)
C7—C2—S1	121.07 (14)	C11—C12—H12	119.5
C4—C3—C2	120.44 (19)	C13—C12—H12	119.5
C4—C3—H3	119.8	C14—C13—C12	120.58 (18)
C2—C3—H3	119.8	C14—C13—H13	119.7
C3—C4—C5	119.93 (19)	C12—C13—H13	119.7
C3—C4—H4	120.0	C13—C14—O2	125.16 (17)
C5—C4—H4	120.0	C13—C14—C15	119.27 (18)
C6—C5—C4	120.3 (2)	O2—C14—C15	115.57 (17)
C6—C5—H5	119.8	O3—C15—C16	124.07 (17)
C4—C5—H5	119.8	O3—C15—C14	116.31 (17)
C5—C6—C7	120.03 (19)	C16—C15—C14	119.61 (17)
C5—C6—H6	120.0	C15—C16—C11	121.03 (17)
C7—C6—H6	120.0	C15—C16—H16	119.5
C6—C7—C2	119.72 (17)	C11—C16—H16	119.5
C6—C7—N1	117.57 (17)	O3—C18—H18A	109.5
C2—C7—N1	122.54 (17)	O3—C18—H18B	109.5
O1—C8—N1	119.77 (17)	H18A—C18—H18B	109.5
O1—C8—C9	119.02 (17)	O3—C18—H18C	109.5
N1—C8—C9	121.21 (18)	H18A—C18—H18C	109.5
C1—C9—C8	122.60 (17)	H18B—C18—H18C	109.5
C1—C9—C10	121.56 (17)	O2—C17—H17A	109.5
C8—C9—C10	115.60 (16)	O2—C17—H17B	109.5
C9—C1—S1	126.33 (15)	H17A—C17—H17B	109.5
C9—C1—H1	116.8	O2—C17—H17C	109.5
S1—C1—H1	116.8	H17A—C17—H17C	109.5
C9—C10—C11	114.99 (15)	H17B—C17—H17C	109.5
C9—C10—H10A	108.5	C8—N1—C7	130.72 (16)
C11—C10—H10A	108.5	C8—N1—H1A	114.6
C9—C10—H10B	108.5	C7—N1—H1A	114.6
C11—C10—H10B	108.5	C15—O3—C18	116.96 (16)
H10A—C10—H10B	107.5	C14—O2—C17	116.60 (16)
C12—C11—C16	118.50 (17)	C1—S1—C2	99.30 (9)
C12—C11—C10	123.88 (16)
C7—C2—C3—C4	0.7 (3)	C11—C12—C13—C14	−1.0 (3)
S1—C2—C3—C4	−176.75 (15)	C12—C13—C14—O2	−179.20 (17)
C2—C3—C4—C5	−2.3 (3)	C12—C13—C14—C15	−0.1 (3)
C3—C4—C5—C6	1.7 (3)	C13—C14—C15—O3	−178.15 (17)
C4—C5—C6—C7	0.5 (3)	O2—C14—C15—O3	1.0 (2)
C5—C6—C7—C2	−2.1 (3)	C13—C14—C15—C16	1.5 (3)
C5—C6—C7—N1	173.30 (16)	O2—C14—C15—C16	−179.36 (16)
C3—C2—C7—C6	1.5 (3)	O3—C15—C16—C11	177.80 (17)
S1—C2—C7—C6	178.92 (13)	C14—C15—C16—C11	−1.8 (3)
C3—C2—C7—N1	−173.68 (16)	C12—C11—C16—C15	0.7 (3)
S1—C2—C7—N1	3.7 (2)	C10—C11—C16—C15	−176.41 (16)
O1—C8—C9—C1	−133.7 (2)	O1—C8—N1—C7	−175.13 (18)
N1—C8—C9—C1	46.7 (3)	C9—C8—N1—C7	4.5 (3)
O1—C8—C9—C10	40.8 (2)	C6—C7—N1—C8	133.3 (2)
N1—C8—C9—C10	−138.76 (18)	C2—C7—N1—C8	−51.4 (3)
C8—C9—C1—S1	−5.3 (3)	C16—C15—O3—C18	−1.4 (3)
C10—C9—C1—S1	−179.56 (14)	C14—C15—O3—C18	178.15 (18)
C1—C9—C10—C11	−113.1 (2)	C13—C14—O2—C17	−15.3 (3)
C8—C9—C10—C11	72.2 (2)	C15—C14—O2—C17	165.61 (18)
C9—C10—C11—C12	14.1 (3)	C9—C1—S1—C2	−58.0 (2)
C9—C10—C11—C16	−168.94 (16)	C3—C2—S1—C1	−125.91 (16)
C16—C11—C12—C13	0.7 (3)	C7—C2—S1—C1	56.68 (17)
C10—C11—C12—C13	177.59 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	2.02	2.863 (2)	167
C18—H18B···O3ii	0.96	2.53	3.445 (3)	159
C4—H4···Cg1iii	0.93	2.57	3.450 (2)	158
C10—H10B···Cg2iv	0.97	2.82	3.725 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C11–C16 and C2–C7 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	2.02	2.863 (2)	167
C18—H18B⋯O3ii	0.96	2.53	3.445 (3)	159
C4—H4⋯Cg1iii	0.93	2.57	3.450 (2)	158
C10—H10B⋯Cg2iv	0.97	2.82	3.725 (2)	155

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