




Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681202661X/hb6847sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S160053681202661X/hb6847Isup2.hkl |
![]() | Chemical Markup Language (CML) file https://doi.org/10.1107/S160053681202661X/hb6847Isup3.cml |
CCDC reference: 889797
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean
(C-C) = 0.003 Å
- R factor = 0.046
- wR factor = 0.146
- Data-to-parameter ratio = 21.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C4 -- C5 .. 5.1 su PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 9 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 53
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............ 1 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 3 ALERT level C = Check. Ensure it is not caused by an omission or oversight 4 ALERT level G = General information/check it is not something unexpected 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 2 ALERT type 5 Informative message, check
A mixture of (Z)-methyl 2-(bromomethyl)-3-(2-methoxyphenyl)acrylate 2 mmol) and o-aminothiophenol (2 mmol) in the presence of potassium tert-butoxide (4.8 mmol) in dry THF (10 ml) was stirred at room temperature for 1 h. After the completion of the reaction as indicated by TLC, the reaction mixture was concentrated and the resulting crude mass was diluted with water (20 ml) and extracted with ethyl acetate (3 x 20 ml). The organic layer was washed with brine (2 x 20 ml) and dried over anhydrous sodium sulfate. The organic layer was concentrated, which successfully provide the crude final product ((Z)-3-(2-methoxybenzyl)benzo[b][1,4]thiazepin-4(5H)-one). The final product was purified by column chromatography on silica gel to afford the title compound in good yield (42%). Recrystallisation from ethyl acetate solution afforded colourless blocks.
H atoms were positioned geometrically, with C–H = 0.93–0.97 Å and constrained to ride on their parent atom, with Uiso(H) =1.5Ueq for methyl H atoms and 1.2Ueq(C) for other H atoms.
The title compound is used as an intermediate for the synthesis of dosulepin, which is an antidepressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). As part of our studies in this area, we now describe the crystal structure of the title compound, (I).
Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) adopts twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 1.0218 (14) Å, θ2 = 74.4 (1)°, φ2 = 178.1 (1)° and φ3 = 174.3 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 47.7 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Sridevi et al., 2011, Sabari et al., 2011).
In the crystal, the molecules at x, y, z and -x, 1-y, -z are linked by N1—H1···O1 hydrogen bonds into cyclic centrosymmetric R22(8) dimers (Bernstein et al., 1995). These dimers are further connected into chains along the a axis via C5—H5···O1 hydrogen bonds (Table 1), resulting in R22(14) ring motifs [Fig. 2; symmetry code as in Fig. 2].
The crystal packing also features two C—H···π interactions, the first one between a H3 atom and neighbouring benene ring (C11–C16), with a C3—H3···Cgiii seperation of 2.69 Å and the second one between methyl H17C atom and neighbouring benzene ring (C11–C16), with a C17—H17C···Cgiv seperation of 2.90 Å (Fig. 3 and Table 1; Cg is the centroid of the C11–C16 benzene ring, Symmetry code as in Fig.3).
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).
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).
C17H15NO2S | Z = 2 |
Mr = 297.36 | F(000) = 312 |
Triclinic, P1 | Dx = 1.303 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6665 (5) Å | Cell parameters from 4197 reflections |
b = 9.7612 (4) Å | θ = 2.2–29.5° |
c = 10.1328 (5) Å | µ = 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 diffractometer | 4137 independent reflections |
Radiation source: fine-focus sealed tube | 2797 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 10.0 pixels mm-1 | θmax = 29.5°, θmin = 2.2° |
ω scans | h = −10→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.951, Tmax = 0.968 | l = −13→14 |
16048 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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0717P)2 + 0.1349P] where P = (Fo2 + 2Fc2)/3 |
4137 reflections | (Δ/σ)max < 0.001 |
191 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.26 e Å−3 |
C17H15NO2S | γ = 103.217 (3)° |
Mr = 297.36 | V = 757.83 (7) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.6665 (5) Å | Mo Kα radiation |
b = 9.7612 (4) Å | µ = 0.22 mm−1 |
c = 10.1328 (5) Å | T = 293 K |
α = 108.181 (3)° | 0.23 × 0.21 × 0.15 mm |
β = 101.561 (2)° |
Bruker APEXII CCD diffractometer | 4137 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2797 reflections with I > 2σ(I) |
Tmin = 0.951, Tmax = 0.968 | Rint = 0.041 |
16048 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.146 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.29 e Å−3 |
4137 reflections | Δρmin = −0.26 e Å−3 |
191 parameters |
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 | 0.1759 (2) | 0.7930 (2) | 0.46956 (18) | 0.0507 (4) | |
H1A | 0.1877 | 0.8740 | 0.5533 | 0.061* | |
C2 | 0.3850 (2) | 0.64173 (18) | 0.39653 (19) | 0.0488 (4) | |
C3 | 0.5478 (2) | 0.6617 (2) | 0.4686 (2) | 0.0608 (5) | |
H3 | 0.5776 | 0.6775 | 0.5668 | 0.073* | |
C4 | 0.6642 (2) | 0.6582 (2) | 0.3954 (3) | 0.0722 (6) | |
H4 | 0.7726 | 0.6702 | 0.4437 | 0.087* | |
C5 | 0.6218 (2) | 0.6371 (3) | 0.2510 (3) | 0.0750 (7) | |
H5 | 0.7016 | 0.6348 | 0.2018 | 0.090* | |
C6 | 0.4611 (2) | 0.6192 (2) | 0.1781 (2) | 0.0599 (5) | |
H6 | 0.4332 | 0.6057 | 0.0803 | 0.072* | |
C7 | 0.34186 (19) | 0.62133 (17) | 0.25091 (18) | 0.0451 (4) | |
C8 | 0.07211 (19) | 0.67234 (17) | 0.20182 (16) | 0.0411 (3) | |
C9 | 0.11639 (19) | 0.80262 (17) | 0.34308 (17) | 0.0424 (4) | |
C10 | 0.0753 (2) | 0.93974 (18) | 0.33034 (18) | 0.0486 (4) | |
H10A | 0.0944 | 1.0126 | 0.4271 | 0.058* | |
H10B | −0.0416 | 0.9100 | 0.2793 | 0.058* | |
C11 | 0.1745 (2) | 1.01587 (18) | 0.25198 (17) | 0.0470 (4) | |
C12 | 0.1171 (2) | 1.11473 (19) | 0.19637 (17) | 0.0513 (4) | |
C13 | 0.2044 (3) | 1.1847 (2) | 0.1219 (2) | 0.0668 (5) | |
H13 | 0.1647 | 1.2489 | 0.0831 | 0.080* | |
C14 | 0.3502 (3) | 1.1584 (3) | 0.1058 (2) | 0.0756 (6) | |
H14 | 0.4084 | 1.2051 | 0.0556 | 0.091* | |
C15 | 0.4107 (3) | 1.0648 (3) | 0.1623 (2) | 0.0704 (6) | |
H15 | 0.5102 | 1.0490 | 0.1521 | 0.085* | |
C16 | 0.3221 (2) | 0.9936 (2) | 0.2350 (2) | 0.0568 (5) | |
H16 | 0.3629 | 0.9294 | 0.2732 | 0.068* | |
C17 | −0.0912 (3) | 1.2357 (2) | 0.1686 (2) | 0.0704 (6) | |
H17A | −0.0129 | 1.3361 | 0.2124 | 0.106* | |
H17B | −0.1929 | 1.2378 | 0.1917 | 0.106* | |
H17C | −0.1121 | 1.2002 | 0.0650 | 0.106* | |
N1 | 0.17774 (16) | 0.59507 (15) | 0.17075 (14) | 0.0454 (3) | |
H1 | 0.1400 | 0.5180 | 0.0899 | 0.055* | |
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) | |
S1 | 0.23445 (6) | 0.63866 (6) | 0.49135 (5) | 0.05956 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0560 (10) | 0.0537 (9) | 0.0413 (8) | 0.0174 (8) | 0.0217 (7) | 0.0116 (7) |
C2 | 0.0453 (9) | 0.0419 (8) | 0.0522 (9) | 0.0133 (7) | 0.0104 (7) | 0.0113 (7) |
C3 | 0.0508 (10) | 0.0505 (10) | 0.0644 (11) | 0.0137 (8) | 0.0004 (9) | 0.0117 (8) |
C4 | 0.0417 (10) | 0.0606 (12) | 0.0915 (16) | 0.0142 (9) | 0.0038 (10) | 0.0098 (11) |
C5 | 0.0451 (11) | 0.0719 (13) | 0.1002 (18) | 0.0195 (9) | 0.0327 (11) | 0.0139 (12) |
C6 | 0.0474 (10) | 0.0650 (11) | 0.0615 (11) | 0.0185 (8) | 0.0232 (8) | 0.0108 (9) |
C7 | 0.0377 (8) | 0.0405 (8) | 0.0489 (9) | 0.0114 (6) | 0.0122 (7) | 0.0070 (6) |
C8 | 0.0380 (8) | 0.0453 (8) | 0.0398 (7) | 0.0105 (6) | 0.0167 (6) | 0.0141 (6) |
C9 | 0.0404 (8) | 0.0444 (8) | 0.0435 (8) | 0.0125 (6) | 0.0207 (7) | 0.0130 (6) |
C10 | 0.0539 (10) | 0.0462 (8) | 0.0507 (9) | 0.0177 (7) | 0.0272 (8) | 0.0158 (7) |
C11 | 0.0503 (9) | 0.0412 (8) | 0.0405 (8) | 0.0065 (7) | 0.0170 (7) | 0.0069 (6) |
C12 | 0.0579 (10) | 0.0475 (9) | 0.0393 (8) | 0.0071 (8) | 0.0151 (7) | 0.0103 (7) |
C13 | 0.0782 (14) | 0.0627 (12) | 0.0582 (11) | 0.0106 (10) | 0.0229 (10) | 0.0274 (9) |
C14 | 0.0785 (15) | 0.0759 (14) | 0.0739 (14) | 0.0068 (11) | 0.0413 (12) | 0.0306 (11) |
C15 | 0.0611 (12) | 0.0689 (13) | 0.0770 (14) | 0.0082 (10) | 0.0382 (11) | 0.0193 (11) |
C16 | 0.0556 (10) | 0.0518 (9) | 0.0580 (10) | 0.0113 (8) | 0.0238 (9) | 0.0134 (8) |
C17 | 0.0779 (14) | 0.0669 (12) | 0.0699 (13) | 0.0253 (11) | 0.0168 (11) | 0.0314 (10) |
N1 | 0.0398 (7) | 0.0468 (7) | 0.0403 (7) | 0.0128 (6) | 0.0114 (5) | 0.0047 (5) |
O1 | 0.0427 (6) | 0.0618 (7) | 0.0467 (6) | 0.0197 (5) | 0.0108 (5) | 0.0092 (5) |
O2 | 0.0643 (8) | 0.0612 (8) | 0.0620 (8) | 0.0232 (6) | 0.0230 (6) | 0.0295 (6) |
S1 | 0.0660 (3) | 0.0692 (3) | 0.0533 (3) | 0.0255 (2) | 0.0227 (2) | 0.0295 (2) |
C1—C9 | 1.323 (2) | C10—C11 | 1.507 (2) |
C1—S1 | 1.7571 (19) | C10—H10A | 0.9700 |
C1—H1A | 0.9300 | C10—H10B | 0.9700 |
C2—C7 | 1.385 (2) | C11—C16 | 1.381 (3) |
C2—C3 | 1.391 (3) | C11—C12 | 1.394 (3) |
C2—S1 | 1.7687 (18) | C12—O2 | 1.364 (2) |
C3—C4 | 1.367 (3) | C12—C13 | 1.386 (3) |
C3—H3 | 0.9300 | C13—C14 | 1.376 (3) |
C4—C5 | 1.371 (3) | C13—H13 | 0.9300 |
C4—H4 | 0.9300 | C14—C15 | 1.365 (4) |
C5—C6 | 1.382 (3) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—C16 | 1.385 (3) |
C6—C7 | 1.386 (2) | C15—H15 | 0.9300 |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—N1 | 1.410 (2) | C17—O2 | 1.421 (2) |
C8—O1 | 1.2353 (19) | C17—H17A | 0.9600 |
C8—N1 | 1.338 (2) | C17—H17B | 0.9600 |
C8—C9 | 1.495 (2) | C17—H17C | 0.9600 |
C9—C10 | 1.497 (2) | N1—H1 | 0.8600 |
C9—C1—S1 | 124.92 (13) | C11—C10—H10B | 108.8 |
C9—C1—H1A | 117.5 | H10A—C10—H10B | 107.7 |
S1—C1—H1A | 117.5 | C16—C11—C12 | 118.41 (16) |
C7—C2—C3 | 119.73 (17) | C16—C11—C10 | 122.51 (17) |
C7—C2—S1 | 120.79 (13) | C12—C11—C10 | 119.07 (15) |
C3—C2—S1 | 119.47 (15) | O2—C12—C13 | 124.34 (18) |
C4—C3—C2 | 120.2 (2) | O2—C12—C11 | 115.28 (15) |
C4—C3—H3 | 119.9 | C13—C12—C11 | 120.37 (18) |
C2—C3—H3 | 119.9 | C14—C13—C12 | 119.5 (2) |
C3—C4—C5 | 120.27 (18) | C14—C13—H13 | 120.2 |
C3—C4—H4 | 119.9 | C12—C13—H13 | 120.2 |
C5—C4—H4 | 119.9 | C15—C14—C13 | 121.1 (2) |
C4—C5—C6 | 120.4 (2) | C15—C14—H14 | 119.4 |
C4—C5—H5 | 119.8 | C13—C14—H14 | 119.4 |
C6—C5—H5 | 119.8 | C14—C15—C16 | 119.2 (2) |
C5—C6—C7 | 119.9 (2) | C14—C15—H15 | 120.4 |
C5—C6—H6 | 120.1 | C16—C15—H15 | 120.4 |
C7—C6—H6 | 120.1 | C11—C16—C15 | 121.4 (2) |
C2—C7—C6 | 119.57 (16) | C11—C16—H16 | 119.3 |
C2—C7—N1 | 122.33 (15) | C15—C16—H16 | 119.3 |
C6—C7—N1 | 118.03 (15) | O2—C17—H17A | 109.5 |
O1—C8—N1 | 120.15 (13) | O2—C17—H17B | 109.5 |
O1—C8—C9 | 118.65 (14) | H17A—C17—H17B | 109.5 |
N1—C8—C9 | 121.18 (14) | O2—C17—H17C | 109.5 |
C1—C9—C8 | 122.35 (15) | H17A—C17—H17C | 109.5 |
C1—C9—C10 | 122.86 (14) | H17B—C17—H17C | 109.5 |
C8—C9—C10 | 114.62 (14) | C8—N1—C7 | 129.58 (13) |
C9—C10—C11 | 113.97 (14) | C8—N1—H1 | 115.2 |
C9—C10—H10A | 108.8 | C7—N1—H1 | 115.2 |
C11—C10—H10A | 108.8 | C12—O2—C17 | 118.25 (15) |
C9—C10—H10B | 108.8 | C1—S1—C2 | 98.07 (8) |
C7—C2—C3—C4 | −1.3 (3) | C16—C11—C12—O2 | −177.21 (14) |
S1—C2—C3—C4 | 177.35 (15) | C10—C11—C12—O2 | 1.7 (2) |
C2—C3—C4—C5 | 0.9 (3) | C16—C11—C12—C13 | 2.0 (2) |
C3—C4—C5—C6 | 0.0 (3) | C10—C11—C12—C13 | −179.04 (16) |
C4—C5—C6—C7 | −0.5 (3) | O2—C12—C13—C14 | 177.81 (17) |
C3—C2—C7—C6 | 0.8 (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—N1 | 177.65 (15) | C13—C14—C15—C16 | 1.0 (3) |
S1—C2—C7—N1 | −1.0 (2) | C12—C11—C16—C15 | −1.2 (3) |
C5—C6—C7—C2 | 0.1 (3) | C10—C11—C16—C15 | 179.90 (17) |
C5—C6—C7—N1 | −176.89 (17) | C14—C15—C16—C11 | −0.3 (3) |
S1—C1—C9—C8 | 7.8 (2) | O1—C8—N1—C7 | 174.44 (16) |
S1—C1—C9—C10 | −177.20 (12) | C9—C8—N1—C7 | −4.2 (3) |
O1—C8—C9—C1 | 131.77 (18) | C2—C7—N1—C8 | 50.9 (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—C17 | 1.0 (3) |
N1—C8—C9—C10 | 135.01 (16) | C11—C12—O2—C17 | −179.81 (15) |
C1—C9—C10—C11 | 118.63 (18) | C9—C1—S1—C2 | 58.22 (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—C1 | 120.55 (15) |
C9—C10—C11—C12 | 161.57 (14) |
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.00 | 2.8545 (17) | 171 |
C5—H5···O1ii | 0.93 | 2.39 | 3.308 (2) | 171 |
C3—H3···Cgiii | 0.93 | 2.69 | 3.432 (2) | 138 |
C17—H17C···Cgiv | 0.96 | 2.90 | 3.664 (2) | 137 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H15NO2S |
Mr | 297.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.6665 (5), 9.7612 (4), 10.1328 (5) |
α, β, γ (°) | 108.181 (3), 101.561 (2), 103.217 (3) |
V (Å3) | 757.83 (7) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.22 |
Crystal size (mm) | 0.23 × 0.21 × 0.15 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.951, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16048, 4137, 2797 |
Rint | 0.041 |
(sin θ/λ)max (Å−1) | 0.692 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.146, 1.01 |
No. of reflections | 4137 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.29, −0.26 |
Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia (1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg is the centroid of the C11–C16 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.00 | 2.8545 (17) | 171 |
C5—H5···O1ii | 0.93 | 2.39 | 3.308 (2) | 171 |
C3—H3···Cgiii | 0.93 | 2.69 | 3.432 (2) | 138 |
C17—H17C···Cgiv | 0.96 | 2.90 | 3.664 (2) | 137 |
Symmetry codes: (i) −x, −y+1, −z; (ii) x+1, y, z; (iii) −x+1, −y+2, −z+1; (iv) −x, −y+2, −z. |
The title compound is used as an intermediate for the synthesis of dosulepin, which is an antidepressant of the tricyclic family. Dosulepin prevents reabsorbing of serotonin and noradrenaline in the brain, helps to prolong the mood lightening effect of any released noradrenaline and serotonin, thus relieving depression. The dibenzo[c,e]thiazepin derivatives exhibit chiroptical properties (Tomascovic et al., 2000). As part of our studies in this area, we now describe the crystal structure of the title compound, (I).
Fig. 1. shows a displacement ellipsoid plot of (I), with the atom numbering scheme. The seven membered thiazepine ring (N1/S1/C1/C2/C7/C8/C9) adopts twist-boat conformation as indicated by puckering parameters (Cremer & Pople, 1975) QT = 1.0218 (14) Å, θ2 = 74.4 (1)°, φ2 = 178.1 (1)° and φ3 = 174.3 (4)°. The dihedral angle between the benzothiazepin ring system and the benzene ring is 47.7 (1)°. The geometric parameters of the title molecule agree well with those reported for similar structures (Sridevi et al., 2011, Sabari et al., 2011).
In the crystal, the molecules at x, y, z and -x, 1-y, -z are linked by N1—H1···O1 hydrogen bonds into cyclic centrosymmetric R22(8) dimers (Bernstein et al., 1995). These dimers are further connected into chains along the a axis via C5—H5···O1 hydrogen bonds (Table 1), resulting in R22(14) ring motifs [Fig. 2; symmetry code as in Fig. 2].
The crystal packing also features two C—H···π interactions, the first one between a H3 atom and neighbouring benene ring (C11–C16), with a C3—H3···Cgiii seperation of 2.69 Å and the second one between methyl H17C atom and neighbouring benzene ring (C11–C16), with a C17—H17C···Cgiv seperation of 2.90 Å (Fig. 3 and Table 1; Cg is the centroid of the C11–C16 benzene ring, Symmetry code as in Fig.3).