Literature DB >> 22798802

(Z)-3-(2-Meth-oxy-benz-yl)-1,5-benzo-thia-zepin-4(5H)-one.

R Selvakumar, M Bakthadoss, D Lakshmanan, S Murugavel.   

Abstract

In the title compound, C(17)H(15)NO(2)S, the seven-membered thia-zepine ring adopts a distorted twist-boat conformation. The dihedral angle between the mean planes of the benzothia-zepin ring system and the attached benzene ring is 47.7 (1)°. In the crystal, pairs of N-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers, generating R(2) (2)(8) ring motifs. These dimers are further connected into a chain along the a axis by C-H⋯O hydrogen bonds, resulting in R(2) (2)(14) ring motifs. The crystal packing also features C-H⋯π inter-actions.

Entities:  

Year:  2012        PMID： 22798802      PMCID： PMC3393937          DOI： 10.1107/S160053681202661X

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For the pharmaceutical properties of thia­zepin derivatives, see: Tomascovic et al. (2000 ▶). For related structures, see: Sridevi et al. (2011 ▶); Sabari et al. 2011 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C17H15NO2S M = 297.36 Triclinic, a = 8.6665 (5) Å b = 9.7612 (4) Å c = 10.1328 (5) Å α = 108.181 (3)° β = 101.561 (2)° γ = 103.217 (3)° V = 757.83 (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 16048 measured reflections 4137 independent reflections 2797 reflections with I > 2σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.046 wR(F 2) = 0.146 S = 1.01 4137 reflections 191 parameters H-atom parameters constrained Δρmax = 0.29 e Å−3 Δρmin = −0.26 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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) global, I. DOI: 10.1107/S160053681202661X/hb6847sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202661X/hb6847Isup2.hkl Supplementary material file. DOI: 10.1107/S160053681202661X/hb6847Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H15NO2SZ = 2
Mr = 297.36F(000) = 312
Triclinic, P1Dx = 1.303 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.6665 (5) ÅCell parameters from 4197 reflections
b = 9.7612 (4) Åθ = 2.2–29.5°
c = 10.1328 (5) ŵ = 0.22 mm−1
α = 108.181 (3)°T = 293 K
β = 101.561 (2)°Block, colourless
γ = 103.217 (3)°0.23 × 0.21 × 0.15 mm
V = 757.83 (7) Å3
Bruker APEXII CCD diffractometer4137 independent reflections
Radiation source: fine-focus sealed tube2797 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 10.0 pixels mm-1θmax = 29.5°, θmin = 2.2°
ω scansh = −10→11
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)k = −13→13
Tmin = 0.951, Tmax = 0.968l = −13→14
16048 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1349P] where P = (Fo2 + 2Fc2)/3
4137 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.29 e Å−3
0 restraintsΔρmin = −0.26 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.
xyzUiso*/Ueq
C10.1759 (2)0.7930 (2)0.46956 (18)0.0507 (4)
H1A0.18770.87400.55330.061*
C20.3850 (2)0.64173 (18)0.39653 (19)0.0488 (4)
C30.5478 (2)0.6617 (2)0.4686 (2)0.0608 (5)
H30.57760.67750.56680.073*
C40.6642 (2)0.6582 (2)0.3954 (3)0.0722 (6)
H40.77260.67020.44370.087*
C50.6218 (2)0.6371 (3)0.2510 (3)0.0750 (7)
H50.70160.63480.20180.090*
C60.4611 (2)0.6192 (2)0.1781 (2)0.0599 (5)
H60.43320.60570.08030.072*
C70.34186 (19)0.62133 (17)0.25091 (18)0.0451 (4)
C80.07211 (19)0.67234 (17)0.20182 (16)0.0411 (3)
C90.11639 (19)0.80262 (17)0.34308 (17)0.0424 (4)
C100.0753 (2)0.93974 (18)0.33034 (18)0.0486 (4)
H10A0.09441.01260.42710.058*
H10B−0.04160.91000.27930.058*
C110.1745 (2)1.01587 (18)0.25198 (17)0.0470 (4)
C120.1171 (2)1.11473 (19)0.19637 (17)0.0513 (4)
C130.2044 (3)1.1847 (2)0.1219 (2)0.0668 (5)
H130.16471.24890.08310.080*
C140.3502 (3)1.1584 (3)0.1058 (2)0.0756 (6)
H140.40841.20510.05560.091*
C150.4107 (3)1.0648 (3)0.1623 (2)0.0704 (6)
H150.51021.04900.15210.085*
C160.3221 (2)0.9936 (2)0.2350 (2)0.0568 (5)
H160.36290.92940.27320.068*
C17−0.0912 (3)1.2357 (2)0.1686 (2)0.0704 (6)
H17A−0.01291.33610.21240.106*
H17B−0.19291.23780.19170.106*
H17C−0.11211.20020.06500.106*
N10.17774 (16)0.59507 (15)0.17075 (14)0.0454 (3)
H10.14000.51800.08990.055*
O1−0.06363 (14)0.63859 (14)0.11211 (12)0.0530 (3)
O2−0.02545 (17)1.13659 (15)0.22258 (14)0.0595 (3)
S10.23445 (6)0.63866 (6)0.49135 (5)0.05956 (17)
U11U22U33U12U13U23
C10.0560 (10)0.0537 (9)0.0413 (8)0.0174 (8)0.0217 (7)0.0116 (7)
C20.0453 (9)0.0419 (8)0.0522 (9)0.0133 (7)0.0104 (7)0.0113 (7)
C30.0508 (10)0.0505 (10)0.0644 (11)0.0137 (8)0.0004 (9)0.0117 (8)
C40.0417 (10)0.0606 (12)0.0915 (16)0.0142 (9)0.0038 (10)0.0098 (11)
C50.0451 (11)0.0719 (13)0.1002 (18)0.0195 (9)0.0327 (11)0.0139 (12)
C60.0474 (10)0.0650 (11)0.0615 (11)0.0185 (8)0.0232 (8)0.0108 (9)
C70.0377 (8)0.0405 (8)0.0489 (9)0.0114 (6)0.0122 (7)0.0070 (6)
C80.0380 (8)0.0453 (8)0.0398 (7)0.0105 (6)0.0167 (6)0.0141 (6)
C90.0404 (8)0.0444 (8)0.0435 (8)0.0125 (6)0.0207 (7)0.0130 (6)
C100.0539 (10)0.0462 (8)0.0507 (9)0.0177 (7)0.0272 (8)0.0158 (7)
C110.0503 (9)0.0412 (8)0.0405 (8)0.0065 (7)0.0170 (7)0.0069 (6)
C120.0579 (10)0.0475 (9)0.0393 (8)0.0071 (8)0.0151 (7)0.0103 (7)
C130.0782 (14)0.0627 (12)0.0582 (11)0.0106 (10)0.0229 (10)0.0274 (9)
C140.0785 (15)0.0759 (14)0.0739 (14)0.0068 (11)0.0413 (12)0.0306 (11)
C150.0611 (12)0.0689 (13)0.0770 (14)0.0082 (10)0.0382 (11)0.0193 (11)
C160.0556 (10)0.0518 (9)0.0580 (10)0.0113 (8)0.0238 (9)0.0134 (8)
C170.0779 (14)0.0669 (12)0.0699 (13)0.0253 (11)0.0168 (11)0.0314 (10)
N10.0398 (7)0.0468 (7)0.0403 (7)0.0128 (6)0.0114 (5)0.0047 (5)
O10.0427 (6)0.0618 (7)0.0467 (6)0.0197 (5)0.0108 (5)0.0092 (5)
O20.0643 (8)0.0612 (8)0.0620 (8)0.0232 (6)0.0230 (6)0.0295 (6)
S10.0660 (3)0.0692 (3)0.0533 (3)0.0255 (2)0.0227 (2)0.0295 (2)
C1—C91.323 (2)C10—C111.507 (2)
C1—S11.7571 (19)C10—H10A0.9700
C1—H1A0.9300C10—H10B0.9700
C2—C71.385 (2)C11—C161.381 (3)
C2—C31.391 (3)C11—C121.394 (3)
C2—S11.7687 (18)C12—O21.364 (2)
C3—C41.367 (3)C12—C131.386 (3)
C3—H30.9300C13—C141.376 (3)
C4—C51.371 (3)C13—H130.9300
C4—H40.9300C14—C151.365 (4)
C5—C61.382 (3)C14—H140.9300
C5—H50.9300C15—C161.385 (3)
C6—C71.386 (2)C15—H150.9300
C6—H60.9300C16—H160.9300
C7—N11.410 (2)C17—O21.421 (2)
C8—O11.2353 (19)C17—H17A0.9600
C8—N11.338 (2)C17—H17B0.9600
C8—C91.495 (2)C17—H17C0.9600
C9—C101.497 (2)N1—H10.8600
C9—C1—S1124.92 (13)C11—C10—H10B108.8
C9—C1—H1A117.5H10A—C10—H10B107.7
S1—C1—H1A117.5C16—C11—C12118.41 (16)
C7—C2—C3119.73 (17)C16—C11—C10122.51 (17)
C7—C2—S1120.79 (13)C12—C11—C10119.07 (15)
C3—C2—S1119.47 (15)O2—C12—C13124.34 (18)
C4—C3—C2120.2 (2)O2—C12—C11115.28 (15)
C4—C3—H3119.9C13—C12—C11120.37 (18)
C2—C3—H3119.9C14—C13—C12119.5 (2)
C3—C4—C5120.27 (18)C14—C13—H13120.2
C3—C4—H4119.9C12—C13—H13120.2
C5—C4—H4119.9C15—C14—C13121.1 (2)
C4—C5—C6120.4 (2)C15—C14—H14119.4
C4—C5—H5119.8C13—C14—H14119.4
C6—C5—H5119.8C14—C15—C16119.2 (2)
C5—C6—C7119.9 (2)C14—C15—H15120.4
C5—C6—H6120.1C16—C15—H15120.4
C7—C6—H6120.1C11—C16—C15121.4 (2)
C2—C7—C6119.57 (16)C11—C16—H16119.3
C2—C7—N1122.33 (15)C15—C16—H16119.3
C6—C7—N1118.03 (15)O2—C17—H17A109.5
O1—C8—N1120.15 (13)O2—C17—H17B109.5
O1—C8—C9118.65 (14)H17A—C17—H17B109.5
N1—C8—C9121.18 (14)O2—C17—H17C109.5
C1—C9—C8122.35 (15)H17A—C17—H17C109.5
C1—C9—C10122.86 (14)H17B—C17—H17C109.5
C8—C9—C10114.62 (14)C8—N1—C7129.58 (13)
C9—C10—C11113.97 (14)C8—N1—H1115.2
C9—C10—H10A108.8C7—N1—H1115.2
C11—C10—H10A108.8C12—O2—C17118.25 (15)
C9—C10—H10B108.8C1—S1—C298.07 (8)
C7—C2—C3—C4−1.3 (3)C16—C11—C12—O2−177.21 (14)
S1—C2—C3—C4177.35 (15)C10—C11—C12—O21.7 (2)
C2—C3—C4—C50.9 (3)C16—C11—C12—C132.0 (2)
C3—C4—C5—C60.0 (3)C10—C11—C12—C13−179.04 (16)
C4—C5—C6—C7−0.5 (3)O2—C12—C13—C14177.81 (17)
C3—C2—C7—C60.8 (3)C11—C12—C13—C14−1.4 (3)
S1—C2—C7—C6−177.84 (13)C12—C13—C14—C15−0.2 (3)
C3—C2—C7—N1177.65 (15)C13—C14—C15—C161.0 (3)
S1—C2—C7—N1−1.0 (2)C12—C11—C16—C15−1.2 (3)
C5—C6—C7—C20.1 (3)C10—C11—C16—C15179.90 (17)
C5—C6—C7—N1−176.89 (17)C14—C15—C16—C11−0.3 (3)
S1—C1—C9—C87.8 (2)O1—C8—N1—C7174.44 (16)
S1—C1—C9—C10−177.20 (12)C9—C8—N1—C7−4.2 (3)
O1—C8—C9—C1131.77 (18)C2—C7—N1—C850.9 (3)
N1—C8—C9—C1−49.6 (2)C6—C7—N1—C8−132.22 (18)
O1—C8—C9—C10−43.6 (2)C13—C12—O2—C171.0 (3)
N1—C8—C9—C10135.01 (16)C11—C12—O2—C17−179.81 (15)
C1—C9—C10—C11118.63 (18)C9—C1—S1—C258.22 (17)
C8—C9—C10—C11−66.03 (18)C7—C2—S1—C1−60.82 (15)
C9—C10—C11—C16−19.6 (2)C3—C2—S1—C1120.55 (15)
C9—C10—C11—C12161.57 (14)
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.002.8545 (17)171
C5—H5···O1ii0.932.393.308 (2)171
C3—H3···Cgiii0.932.693.432 (2)138
C17—H17C···Cgiv0.962.903.664 (2)137
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A D—HH⋯A D⋯A D—H⋯A
N1—H1⋯O1i 0.862.002.8545 (17)171
C5—H5⋯O1ii 0.932.393.308 (2)171
C3—H3⋯Cg iii 0.932.693.432 (2)138
C17—H17C⋯Cg iv 0.962.903.664 (2)137

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

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1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  3-(2-Methyl-benzyl-idene)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

Authors:  D Sridevi; Sundari Bhaskaran; G Usha; G Murugan; M Bakthadoss
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-01-08

3.  3-[(Z)-Benzyl-idene]-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

Authors:  V Sabari; G Jagadeesan; Raman Selvakumar; Mannickam Bakthadoss; S Aravindhan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-10-29

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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1.  Crystal structure of (Z)-3-(4-meth-oxy-benzyl-idene)-2,3-di-hydro-benzo[b][1,4]thia-zepin-4(5H)-one.

Authors:  V Vinayagam; J Mohan Raj; S Murugavel; R Selvakumar; M Bakthadoss
Journal:  Acta Crystallogr E Crystallogr Commun       Date:  2015-01-01

2.  (Z)-3-(3,4-Dimeth-oxy-benzyl-idene)-2,3-dihydro-1,5-benzothia-zepin-4(5H)-one.

Authors:  M Bakthadoss; R Selvakumar; N Manikandan; S Murugavel
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2013-03-23

3.  (Z)-3-(4-Chloro-benz-yl)-1,5-benzothia-zepin-4(5H)-one.

Authors:  D Lakshmanan; S Murugavel; R Selvakumar; M Bakthadoss
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-06-16
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