organic compounds
6-Bromo-2-[(E)-thiophen-2-ylmethylidene]-2,3,4,9-tetrahydro-1H-carbazol-1-one
aPost Graduate and Research Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore 641 020, India, bDepartment of Engineering Chemistry, Christ University, Bangalore 560 029, India, and cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
*Correspondence e-mail: mnpsy2004@yahoo.com
In the title compound, C17H12BrNOS, the cyclohexene ring deviates only slightly from planarity (r.m.s. deviation for non-H atoms = 0.047 Å). In the crystal, the molecules are linked into centrosymmetric R22(10) dimers via pairs of N—H⋯O hydrogen bonds. The thiophene ring is disordered over two positions rotated by 180° and with a site-occupation factor of 0.843 (4) for the major occupied site.
Related literature
For the biological activity of carbazole derivatives, see: Magnus et al. (1992); Abraham (1975); Saxton (1983); Phillipson & Zenk (1980); Bergman & Pelcman (1990); Bonesi et al. (2004); Chakraborty et al. (1965); Kirtikar & Basu (1933); Chakraborty et al. (1973); Savini et al. (2004). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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).
Supporting information
https://doi.org/10.1107/S1600536811046551/bt5684sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046551/bt5684Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046551/bt5684Isup3.cml
The mixed aldol condensation reaction of 6-bromo-1-oxo-1,2,3, 4-tetrahydrocarbazole reacted with thiophene-2-carbaldehyde in the presence of alcoholic KOH, afforded a single product, substituted 6-bromo-2- thiofuran-2-ylmethylene-2,3,4,9-tetrahydro-carbazol-1-one. This was purified by using
over silica gel (mesh 60–80). During elution of the column with petroleum ether (60–80°C) and ethyl acetate [1:2] mixture, a yellowish solid was obtained. The crystals of the title compound suitable for single XRD analysis were obtained by the slow evaporation method using the solvent mixture ethyl acetate and acetone (8:2) at room temperature.N-bound H atom was located in a difference map and refined isotropically. C-bound H atoms were positioned geometrically (C–H = 0.93–0.97 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for all other H atoms. The thiophene ring is disordered over two positions rotated by 180 degrees and with a site occupation factor of 0.843 (4) for the major occupied site.
Carbazole
obtained from naturally occurring sources have been the subject of extensive research, mainly because of their widespread applications in traditional medicine (Bergman & Pelcman, 1990; Bonesi et al., 2004; Chakraborty et al., 1965; Kirtikar & Basu, 1933). Tetrahydrocarbazole systems are present in the framework of a number of indole-type of biological interest (Magnus et al., 1992; Abraham, 1975; Saxton, 1983; Phillipson et al., 1980). These types of compounds possess significant antibiotic, anti-carcinogenic, antiviral and anti-inflammatory properties (Chakraborty et al., 1973). The thiophene derivatives possess the antimicrobial activity (Savini et al., 2004). Against this background and to ascertain the molecular structure and conformation, the X-ray determination of the title compound has been carried out.The ORTEP plot of the molecule is shown in Fig. 1. The cyclohexene ring in the carbazole ring system adopts φ2 = 102.0 (2)° and Δs(C10 & C13)= 4.4 (5)°. Thiophene ring in the molecule is planar conformation. The sum of the bond angles around N1 [359.3°] is in accordance with sp2 hybridization.
with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q2=0.126 (5) Å, q3 = 0.050 (4) Å,The molecules at (x, y, z) and (-x + 2, -y + 1, -z) are linked by N1—H1···O1 hydrogen bonds into a cyclic centrosymmetric R22(14) dimer.
For the biological activity of carbazole derivatives, see: Magnus et al. (1992); Abraham (1975); Saxton (1983); Phillipson & Zenk (1980); Bergman & Pelcman (1990); Bonesi et al. (2004); Chakraborty et al. (1965); Kirtikar & Basu (1933); Chakraborty et al. (1973); Savini et al. (2004). For puckering parameters, see: Cremer & Pople (1975). For asymmetry parameters, see: Nardelli (1983). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: SMART (Bruker, 1998); cell
SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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).C17H12BrNOS | F(000) = 720 |
Mr = 358.25 | Dx = 1.604 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1432 reflections |
a = 13.8655 (5) Å | θ = 2.4–30.5° |
b = 6.3081 (3) Å | µ = 2.91 mm−1 |
c = 17.4583 (7) Å | T = 296 K |
β = 103.666 (2)° | Block, yellow |
V = 1483.76 (11) Å3 | 0.21 × 0.17 × 0.16 mm |
Z = 4 |
Bruker SMART APEX CCD detector diffractometer | 4487 independent reflections |
Radiation source: fine-focus sealed tube | 1953 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 30.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −19→19 |
Tmin = 0.558, Tmax = 0.628 | k = −4→8 |
12158 measured reflections | l = −24→24 |
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)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.85 | w = 1/[σ2(Fo2) + (0.0752P)2 + 0.4371P] where P = (Fo2 + 2Fc2)/3 |
4487 reflections | (Δ/σ)max = 0.002 |
191 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C17H12BrNOS | V = 1483.76 (11) Å3 |
Mr = 358.25 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.8655 (5) Å | µ = 2.91 mm−1 |
b = 6.3081 (3) Å | T = 296 K |
c = 17.4583 (7) Å | 0.21 × 0.17 × 0.16 mm |
β = 103.666 (2)° |
Bruker SMART APEX CCD detector diffractometer | 4487 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 1953 reflections with I > 2σ(I) |
Tmin = 0.558, Tmax = 0.628 | Rint = 0.044 |
12158 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.85 | Δρmax = 0.49 e Å−3 |
4487 reflections | Δρmin = −0.31 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 | Occ. (<1) | |
Br1 | 1.44365 (3) | −0.32770 (7) | 0.06412 (3) | 0.0742 (2) | |
S1 | 0.76193 (8) | −0.1866 (2) | 0.24215 (7) | 0.0665 (5) | 0.843 (4) |
C18' | 0.76193 (8) | −0.1866 (2) | 0.24215 (7) | 0.0665 (5) | 0.157 (4) |
H18' | 0.8144 | −0.2822 | 0.2546 | 0.080* | 0.157 (4) |
O1 | 0.91041 (18) | 0.3896 (4) | 0.06209 (14) | 0.0557 (6) | |
N1 | 1.1050 (2) | 0.2754 (5) | 0.04571 (15) | 0.0474 (7) | |
H1 | 1.0940 | 0.4036 | 0.0258 | 0.057* | |
C2 | 1.1893 (2) | 0.1612 (5) | 0.04737 (18) | 0.0419 (8) | |
C3 | 1.2698 (3) | 0.2105 (6) | 0.0147 (2) | 0.0546 (10) | |
H3 | 1.2722 | 0.3377 | −0.0117 | 0.066* | |
C4 | 1.3444 (3) | 0.0657 (7) | 0.0229 (2) | 0.0569 (10) | |
H4 | 1.3992 | 0.0949 | 0.0026 | 0.068* | |
C5 | 1.3393 (2) | −0.1272 (6) | 0.0619 (2) | 0.0523 (9) | |
C6 | 1.2619 (2) | −0.1797 (6) | 0.09508 (19) | 0.0458 (8) | |
H6 | 1.2604 | −0.3082 | 0.1209 | 0.055* | |
C7 | 1.1855 (2) | −0.0306 (5) | 0.08814 (16) | 0.0401 (7) | |
C8 | 1.0929 (2) | −0.0273 (5) | 0.11198 (16) | 0.0380 (7) | |
C9 | 1.0491 (3) | −0.1861 (6) | 0.1562 (2) | 0.0556 (10) | |
H9A | 1.0982 | −0.2242 | 0.2037 | 0.067* | |
H9B | 1.0334 | −0.3129 | 0.1243 | 0.067* | |
C10 | 0.9568 (3) | −0.1110 (6) | 0.1789 (2) | 0.0598 (10) | |
H10A | 0.9104 | −0.2286 | 0.1706 | 0.072* | |
H10B | 0.9746 | −0.0836 | 0.2352 | 0.072* | |
C11 | 0.9014 (2) | 0.0798 (5) | 0.14016 (17) | 0.0405 (7) | |
C12 | 0.9501 (2) | 0.2235 (6) | 0.09254 (18) | 0.0413 (8) | |
C13 | 1.0475 (2) | 0.1591 (5) | 0.08458 (17) | 0.0412 (8) | |
C14 | 0.8096 (2) | 0.1348 (6) | 0.14535 (19) | 0.0472 (8) | |
H14 | 0.7854 | 0.2568 | 0.1174 | 0.057* | |
C15 | 0.7412 (2) | 0.0388 (6) | 0.18652 (17) | 0.0480 (9) | |
C16 | 0.6513 (3) | −0.1697 (8) | 0.2658 (2) | 0.0711 (13) | |
H16 | 0.6297 | −0.2663 | 0.2984 | 0.085* | |
C17 | 0.5980 (3) | −0.0032 (9) | 0.2330 (3) | 0.0820 (14) | |
H17 | 0.5350 | 0.0233 | 0.2406 | 0.098* | |
S1' | 0.6432 (3) | 0.1340 (6) | 0.1851 (2) | 0.0920 (14) | 0.157 (4) |
C18 | 0.6432 (3) | 0.1340 (6) | 0.1851 (2) | 0.0920 (14) | 0.843 (4) |
H18 | 0.6164 | 0.2565 | 0.1589 | 0.110* | 0.843 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0607 (3) | 0.0682 (3) | 0.1064 (4) | −0.0012 (2) | 0.0451 (2) | −0.0058 (2) |
S1 | 0.0530 (7) | 0.0737 (10) | 0.0782 (8) | −0.0023 (6) | 0.0263 (6) | 0.0248 (7) |
C18' | 0.0530 (7) | 0.0737 (10) | 0.0782 (8) | −0.0023 (6) | 0.0263 (6) | 0.0248 (7) |
O1 | 0.0592 (14) | 0.0422 (14) | 0.0678 (15) | 0.0038 (13) | 0.0193 (12) | 0.0176 (13) |
N1 | 0.0558 (17) | 0.0388 (16) | 0.0505 (16) | −0.0049 (14) | 0.0180 (13) | 0.0134 (14) |
C2 | 0.0544 (18) | 0.0353 (18) | 0.0381 (16) | −0.0101 (17) | 0.0152 (14) | 0.0008 (15) |
C3 | 0.064 (2) | 0.053 (2) | 0.0515 (19) | −0.019 (2) | 0.0240 (17) | 0.0035 (18) |
C4 | 0.058 (2) | 0.064 (3) | 0.057 (2) | −0.017 (2) | 0.0289 (17) | −0.003 (2) |
C5 | 0.0466 (18) | 0.057 (2) | 0.057 (2) | −0.0071 (18) | 0.0210 (16) | −0.0063 (19) |
C6 | 0.0471 (18) | 0.044 (2) | 0.0508 (18) | −0.0068 (17) | 0.0199 (15) | 0.0014 (17) |
C7 | 0.0489 (17) | 0.0386 (19) | 0.0349 (15) | −0.0072 (16) | 0.0141 (14) | −0.0016 (15) |
C8 | 0.0455 (16) | 0.0348 (18) | 0.0352 (15) | −0.0046 (15) | 0.0127 (13) | 0.0018 (15) |
C9 | 0.054 (2) | 0.049 (2) | 0.071 (2) | 0.0043 (18) | 0.0288 (18) | 0.0206 (19) |
C10 | 0.066 (2) | 0.054 (2) | 0.071 (2) | 0.009 (2) | 0.0374 (19) | 0.023 (2) |
C11 | 0.0510 (18) | 0.0354 (18) | 0.0364 (15) | −0.0037 (16) | 0.0129 (14) | −0.0020 (15) |
C12 | 0.0490 (18) | 0.0353 (19) | 0.0395 (16) | −0.0046 (16) | 0.0099 (14) | −0.0004 (16) |
C13 | 0.0471 (17) | 0.0367 (19) | 0.0408 (16) | −0.0073 (16) | 0.0122 (14) | 0.0006 (16) |
C14 | 0.0522 (19) | 0.044 (2) | 0.0455 (18) | −0.0011 (17) | 0.0112 (15) | 0.0072 (16) |
C15 | 0.0454 (17) | 0.059 (2) | 0.0402 (16) | −0.0049 (18) | 0.0108 (14) | 0.0017 (17) |
C16 | 0.052 (2) | 0.093 (4) | 0.073 (3) | −0.014 (2) | 0.022 (2) | 0.016 (3) |
C17 | 0.056 (2) | 0.117 (4) | 0.079 (3) | 0.004 (3) | 0.027 (2) | 0.005 (3) |
S1' | 0.084 (2) | 0.106 (3) | 0.093 (2) | −0.006 (2) | 0.0363 (18) | 0.011 (2) |
C18 | 0.084 (2) | 0.106 (3) | 0.093 (2) | −0.006 (2) | 0.0363 (18) | 0.011 (2) |
Br1—C5 | 1.915 (4) | C8—C9 | 1.480 (4) |
S1—C16 | 1.683 (4) | C9—C10 | 1.503 (4) |
S1—C15 | 1.707 (4) | C9—H9A | 0.9700 |
O1—C12 | 1.243 (4) | C9—H9B | 0.9700 |
N1—C2 | 1.368 (4) | C10—C11 | 1.500 (5) |
N1—C13 | 1.375 (4) | C10—H10A | 0.9700 |
N1—H1 | 0.8789 | C10—H10B | 0.9700 |
C2—C3 | 1.403 (4) | C11—C14 | 1.343 (4) |
C2—C7 | 1.411 (4) | C11—C12 | 1.495 (4) |
C3—C4 | 1.361 (5) | C12—C13 | 1.448 (4) |
C3—H3 | 0.9300 | C14—C15 | 1.451 (4) |
C4—C5 | 1.403 (5) | C14—H14 | 0.9300 |
C4—H4 | 0.9300 | C15—S1' | 1.480 (4) |
C5—C6 | 1.376 (4) | C16—C17 | 1.333 (6) |
C6—C7 | 1.400 (4) | C16—H16 | 0.9300 |
C6—H6 | 0.9300 | C17—S1' | 1.445 (6) |
C7—C8 | 1.441 (4) | C17—H17 | 0.9300 |
C8—C13 | 1.366 (4) | ||
C16—S1—C15 | 92.6 (2) | H9A—C9—H9B | 107.7 |
C2—N1—C13 | 107.5 (3) | C11—C10—C9 | 120.7 (3) |
C2—N1—H1 | 124.1 | C11—C10—H10A | 107.1 |
C13—N1—H1 | 128.2 | C9—C10—H10A | 107.1 |
N1—C2—C3 | 129.2 (3) | C11—C10—H10B | 107.1 |
N1—C2—C7 | 109.2 (3) | C9—C10—H10B | 107.1 |
C3—C2—C7 | 121.5 (3) | H10A—C10—H10B | 106.8 |
C4—C3—C2 | 117.7 (3) | C14—C11—C12 | 116.2 (3) |
C4—C3—H3 | 121.1 | C14—C11—C10 | 124.7 (3) |
C2—C3—H3 | 121.1 | C12—C11—C10 | 119.1 (3) |
C3—C4—C5 | 120.6 (3) | O1—C12—C13 | 121.6 (3) |
C3—C4—H4 | 119.7 | O1—C12—C11 | 122.5 (3) |
C5—C4—H4 | 119.7 | C13—C12—C11 | 115.9 (3) |
C6—C5—C4 | 123.1 (3) | C8—C13—N1 | 111.1 (3) |
C6—C5—Br1 | 119.5 (3) | C8—C13—C12 | 124.8 (3) |
C4—C5—Br1 | 117.3 (2) | N1—C13—C12 | 124.1 (3) |
C5—C6—C7 | 116.8 (3) | C11—C14—C15 | 131.8 (3) |
C5—C6—H6 | 121.6 | C11—C14—H14 | 114.1 |
C7—C6—H6 | 121.6 | C15—C14—H14 | 114.1 |
C6—C7—C2 | 120.1 (3) | C14—C15—S1' | 121.8 (3) |
C6—C7—C8 | 133.8 (3) | C14—C15—S1 | 126.0 (3) |
C2—C7—C8 | 106.0 (3) | S1'—C15—S1 | 112.2 (2) |
C13—C8—C7 | 106.3 (3) | C17—C16—S1 | 112.9 (3) |
C13—C8—C9 | 123.6 (3) | C17—C16—H16 | 123.6 |
C7—C8—C9 | 130.1 (3) | S1—C16—H16 | 123.6 |
C8—C9—C10 | 113.8 (3) | C16—C17—S1' | 116.6 (4) |
C8—C9—H9A | 108.8 | C16—C17—H17 | 121.7 |
C10—C9—H9A | 108.8 | S1'—C17—H17 | 121.7 |
C8—C9—H9B | 108.8 | C17—S1'—C15 | 105.6 (3) |
C10—C9—H9B | 108.8 | ||
C13—N1—C2—C3 | 178.8 (3) | C10—C11—C12—O1 | −176.4 (3) |
C13—N1—C2—C7 | −0.2 (3) | C14—C11—C12—C13 | −177.7 (3) |
N1—C2—C3—C4 | −178.3 (3) | C10—C11—C12—C13 | 2.9 (4) |
C7—C2—C3—C4 | 0.6 (5) | C7—C8—C13—N1 | −0.6 (3) |
C2—C3—C4—C5 | 1.0 (5) | C9—C8—C13—N1 | −180.0 (3) |
C3—C4—C5—C6 | −1.5 (6) | C7—C8—C13—C12 | 177.2 (3) |
C3—C4—C5—Br1 | 175.9 (3) | C9—C8—C13—C12 | −2.2 (5) |
C4—C5—C6—C7 | 0.4 (5) | C2—N1—C13—C8 | 0.5 (4) |
Br1—C5—C6—C7 | −176.9 (2) | C2—N1—C13—C12 | −177.4 (3) |
C5—C6—C7—C2 | 1.1 (5) | O1—C12—C13—C8 | −175.6 (3) |
C5—C6—C7—C8 | 177.9 (3) | C11—C12—C13—C8 | 5.2 (4) |
N1—C2—C7—C6 | 177.4 (3) | O1—C12—C13—N1 | 2.0 (5) |
C3—C2—C7—C6 | −1.6 (5) | C11—C12—C13—N1 | −177.3 (3) |
N1—C2—C7—C8 | −0.2 (3) | C12—C11—C14—C15 | −178.8 (3) |
C3—C2—C7—C8 | −179.3 (3) | C10—C11—C14—C15 | 0.6 (6) |
C6—C7—C8—C13 | −176.7 (3) | C11—C14—C15—S1' | 178.2 (4) |
C2—C7—C8—C13 | 0.5 (3) | C11—C14—C15—S1 | −0.6 (6) |
C6—C7—C8—C9 | 2.7 (6) | C16—S1—C15—C14 | 178.6 (3) |
C2—C7—C8—C9 | 179.8 (3) | C16—S1—C15—S1' | −0.4 (3) |
C13—C8—C9—C10 | −8.5 (5) | C15—S1—C16—C17 | 0.8 (4) |
C7—C8—C9—C10 | 172.2 (3) | S1—C16—C17—S1' | −1.1 (6) |
C8—C9—C10—C11 | 16.1 (5) | C16—C17—S1'—C15 | 0.8 (5) |
C9—C10—C11—C14 | 166.8 (4) | C14—C15—S1'—C17 | −179.2 (3) |
C9—C10—C11—C12 | −13.8 (5) | S1—C15—S1'—C17 | −0.2 (4) |
C14—C11—C12—O1 | 3.0 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1 | 0.93 | 2.33 | 2.759 (4) | 108 |
N1—H1···O1i | 0.88 | 2.00 | 2.804 (4) | 151 |
Symmetry code: (i) −x+2, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C17H12BrNOS |
Mr | 358.25 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 296 |
a, b, c (Å) | 13.8655 (5), 6.3081 (3), 17.4583 (7) |
β (°) | 103.666 (2) |
V (Å3) | 1483.76 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.91 |
Crystal size (mm) | 0.21 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.558, 0.628 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12158, 4487, 1953 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.714 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.148, 0.85 |
No. of reflections | 4487 |
No. of parameters | 191 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.49, −0.31 |
Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
C14—H14···O1 | 0.93 | 2.33 | 2.759 (4) | 107.7 |
N1—H1···O1i | 0.88 | 2.00 | 2.804 (4) | 150.7 |
Symmetry code: (i) −x+2, −y+1, −z. |
Acknowledgements
The authors thank the Solid State Unit, Indian Institute of Science, Bangalore, India, for the data collection and and Dr A. Chandramohan, Post Graduate and Research Department of Chemistry, Sri Ramakrishna Mission Vidyalaya College of Arts and Science, Coimbatore, for his valuable suggestions.
References
Abraham, D. J. (1975). The Catharanthus Alkaloids, edited by W. I. Taylor & N. R. Farnsworth, chs. 7 and 8. New York: Marcel Decker. Google Scholar
Bergman, J. & Pelcman, B. (1990). Pure Appl. Chem. 62, 1967–1976. CrossRef CAS Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bonesi, S. M., Crevatin, L. K. & Erra-Balsells, R. (2004). Photochem. Photobiol. Sci. 3, 381–388. Web of Science CrossRef PubMed CAS Google Scholar
Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconcin, USA. Google Scholar
Chakraborty, D. P., Barman, B. K. & Bose, P. K. (1965). Tetrahedron, 21, 681–685. CrossRef CAS Web of Science Google Scholar
Chakraborty, D. P., Das, K. C., Das, B. P. & Chowdhury, B. K. (1973). Trans. Bose Res. Inst. 38, 1–10. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Kirtikar, K. R. & Basu, B. D. (1933). Indian Medicinal Plants, edited by L. M. Basu, 2nd ed., pp. 2131–2133. Allahabad: Central Council for Research in Ayurveda & Siddha (Deptt. of AYUSH, Min. of Health & Family Welfare), Govt. of India. Google Scholar
Magnus, P., Sear, N. L., Kim, C. S. & Vicker, N. (1992). J. Org. Chem. 57, 70–78. CSD CrossRef CAS Web of Science Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Phillipson, J. D. & Zenk, M. H. (1980). Indole and Biogenetically Related Alkaloids, ch 3. New York: Academic Press. Google Scholar
Savini, L., Chiasserini, L., Travagli, V., Pellerano, C., Novellino, E., Cosentino, S. & Pisano, M. B. (2004). Eur. J. Med. Chem. 39, 113–122. Web of Science CrossRef PubMed CAS Google Scholar
Saxton, J. E. (1983). Editor. Heterocyclic Compounds, Vol. 25, The Monoterpenoid Indole Alkaloids, chs. 8 and 11. New York: Wiley. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Carbazole alkaloids obtained from naturally occurring sources have been the subject of extensive research, mainly because of their widespread applications in traditional medicine (Bergman & Pelcman, 1990; Bonesi et al., 2004; Chakraborty et al., 1965; Kirtikar & Basu, 1933). Tetrahydrocarbazole systems are present in the framework of a number of indole-type alkaloids of biological interest (Magnus et al., 1992; Abraham, 1975; Saxton, 1983; Phillipson et al., 1980). These types of compounds possess significant antibiotic, anti-carcinogenic, antiviral and anti-inflammatory properties (Chakraborty et al., 1973). The thiophene derivatives possess the antimicrobial activity (Savini et al., 2004). Against this background and to ascertain the molecular structure and conformation, the X-ray crystal structure determination of the title compound has been carried out.
The ORTEP plot of the molecule is shown in Fig. 1. The cyclohexene ring in the carbazole ring system adopts envelope conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q2=0.126 (5) Å, q3 = 0.050 (4) Å, φ2 = 102.0 (2)° and Δs(C10 & C13)= 4.4 (5)°. Thiophene ring in the molecule is planar conformation. The sum of the bond angles around N1 [359.3°] is in accordance with sp2 hybridization.
The molecules at (x, y, z) and (-x + 2, -y + 1, -z) are linked by N1—H1···O1 hydrogen bonds into a cyclic centrosymmetric R22(14) dimer.