organic compounds
6-Bromo-2-(3-phenylallylidene)-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, Karnataka, 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
Molecules of the title compound, C21H16BrNO, are linked through pairs of N—H⋯O intermolecular hydrogen bonds into centrosymmetric R22(10) dimers. One of the C atoms of the cyclohex-2-enone ring is disordered with refined occupancies of 0.61 (2) and 0.39 (2).
Related literature
For the biological activity of carbazole derivatives, see: Shufen et al. (1995); 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); Knolker & Reddy, 2002. 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/S1600536811046563/bt5677sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046563/bt5677Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811046563/bt5677Isup3.cml
The mixed aldol condensation reaction of 6-bromo-1-oxo-1,2,3, 4-tetrahydrocarbazole reacted with cinnamaldehyde in the presence of alcoholic KOH, afforded a single product, substituted 6-Bromo-2-(3-phenyl-allylidene) -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. It was recrystallized from the solvent mixture ethyl acetate and acetone (8:2).The 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) = 1.2Ueq(C) for all H atoms.
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). Aminocarbazoles are widely used as intermediates for the preparation of carbazole-based synthetic dyes, agrochemicals, pharmaceuticals and light-sensitive materials (Shufen et al., 1995). 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 chemists have been attracted towards these compounds due to their biological activities and potential applications as pharmacological agents (Knolker & Reddy, 2002). 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. One of the C atoms of the cyclohexane ring is disordered with refined occupancies of 0.61 (2) and 0.39 (2). The disordered position of C10B in the cyclohexane ring in the carbazole ring system adopts φ2 = 117.3 (13)° and Δs(C10B & C13)= 1.5 (5)°. The sum of the bond angles around N1 [358.3°] is in accordance with sp2 hybridization.
with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q2=0.242 (7) Å, q3 = 0.171 (6) Å,The crystal packing reveals that symmetry-related molecules are linked through N—H···O intermolecular hydrogen bonds into cyclic centrosymmetric R22(10) dimers.
For the biological activity of carbazole derivatives, see: Shufen et al. (1995); 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); Knolker & Reddy, 2002. 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).C21H16BrNO | F(000) = 768 |
Mr = 378.26 | Dx = 1.444 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2134 reflections |
a = 17.3682 (7) Å | θ = 1.2–28.3° |
b = 14.9974 (8) Å | µ = 2.37 mm−1 |
c = 6.6861 (3) Å | T = 293 K |
β = 92.226 (2)° | Block, yellow |
V = 1740.27 (14) Å3 | 0.20 × 0.17 × 0.16 mm |
Z = 4 |
Bruker SMART APEX CCD detector diffractometer | 4319 independent reflections |
Radiation source: fine-focus sealed tube | 2158 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
ω scans | θmax = 28.3°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −23→23 |
Tmin = 0.629, Tmax = 0.685 | k = −18→20 |
16684 measured reflections | l = −8→8 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0592P)2 + 0.6068P] where P = (Fo2 + 2Fc2)/3 |
4319 reflections | (Δ/σ)max < 0.001 |
231 parameters | Δρmax = 0.46 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
C21H16BrNO | V = 1740.27 (14) Å3 |
Mr = 378.26 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.3682 (7) Å | µ = 2.37 mm−1 |
b = 14.9974 (8) Å | T = 293 K |
c = 6.6861 (3) Å | 0.20 × 0.17 × 0.16 mm |
β = 92.226 (2)° |
Bruker SMART APEX CCD detector diffractometer | 4319 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2158 reflections with I > 2σ(I) |
Tmin = 0.629, Tmax = 0.685 | Rint = 0.044 |
16684 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.137 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.97 | Δρmax = 0.46 e Å−3 |
4319 reflections | Δρmin = −0.55 e Å−3 |
231 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 | 0.39020 (2) | 0.32240 (3) | 0.51370 (6) | 0.1026 (2) | |
O1 | −0.08065 (12) | 0.45133 (15) | 0.1631 (3) | 0.0688 (6) | |
N1 | 0.08292 (14) | 0.42507 (17) | 0.1535 (3) | 0.0552 (6) | |
H1 | 0.0713 (17) | 0.458 (2) | 0.059 (4) | 0.067 (9)* | |
C2 | 0.15712 (17) | 0.40282 (18) | 0.2075 (4) | 0.0528 (7) | |
C3 | 0.22410 (18) | 0.4135 (2) | 0.1039 (4) | 0.0641 (8) | |
H3 | 0.2229 | 0.4378 | −0.0242 | 0.077* | |
C4 | 0.29216 (19) | 0.3873 (2) | 0.1963 (5) | 0.0675 (8) | |
H4 | 0.3381 | 0.3937 | 0.1306 | 0.081* | |
C5 | 0.2929 (2) | 0.3509 (2) | 0.3901 (5) | 0.0692 (9) | |
C6 | 0.22789 (19) | 0.3375 (2) | 0.4921 (4) | 0.0622 (8) | |
H6 | 0.2299 | 0.3118 | 0.6187 | 0.075* | |
C7 | 0.15750 (17) | 0.36386 (18) | 0.4003 (4) | 0.0505 (7) | |
C8 | 0.08023 (17) | 0.36309 (18) | 0.4592 (3) | 0.0485 (6) | |
C9 | 0.04470 (19) | 0.3290 (2) | 0.6440 (4) | 0.0658 (8) | |
H9A | 0.0487 | 0.2645 | 0.6453 | 0.079* | 0.61 (2) |
H9B | 0.0743 | 0.3513 | 0.7595 | 0.079* | 0.61 (2) |
H9C | 0.0547 | 0.3712 | 0.7519 | 0.079* | 0.39 (2) |
H9D | 0.0691 | 0.2730 | 0.6823 | 0.079* | 0.39 (2) |
C11 | −0.08446 (18) | 0.38062 (19) | 0.4825 (4) | 0.0538 (7) | |
C12 | −0.04532 (17) | 0.41447 (18) | 0.3044 (3) | 0.0506 (7) | |
C13 | 0.03659 (16) | 0.40161 (17) | 0.3067 (3) | 0.0477 (6) | |
C14 | −0.15949 (18) | 0.3978 (2) | 0.4961 (4) | 0.0586 (7) | |
H14 | −0.1826 | 0.4283 | 0.3886 | 0.070* | |
C15 | −0.20892 (18) | 0.3753 (2) | 0.6550 (4) | 0.0631 (8) | |
H15 | −0.1887 | 0.3416 | 0.7613 | 0.076* | |
C16 | −0.28207 (19) | 0.4001 (2) | 0.6583 (4) | 0.0676 (8) | |
H16 | −0.3011 | 0.4311 | 0.5464 | 0.081* | |
C17 | −0.33642 (18) | 0.3850 (2) | 0.8155 (5) | 0.0658 (8) | |
C18 | −0.3143 (2) | 0.3524 (2) | 1.0019 (5) | 0.0780 (10) | |
H18 | −0.2625 | 0.3403 | 1.0313 | 0.094* | |
C19 | −0.3677 (3) | 0.3376 (3) | 1.1451 (6) | 0.0984 (13) | |
H19 | −0.3521 | 0.3145 | 1.2692 | 0.118* | |
C20 | −0.4435 (3) | 0.3568 (3) | 1.1050 (8) | 0.1123 (16) | |
H20 | −0.4795 | 0.3470 | 1.2019 | 0.135* | |
C21 | −0.4661 (2) | 0.3902 (4) | 0.9231 (8) | 0.1155 (16) | |
H21 | −0.5178 | 0.4033 | 0.8962 | 0.139* | |
C22 | −0.4137 (2) | 0.4048 (3) | 0.7794 (6) | 0.0882 (11) | |
H22 | −0.4300 | 0.4282 | 0.6561 | 0.106* | |
C10A | −0.0342 (11) | 0.3529 (15) | 0.665 (2) | 0.058 (4) | 0.39 (2) |
H10A | −0.0353 | 0.4016 | 0.7602 | 0.069* | 0.39 (2) |
H10B | −0.0594 | 0.3026 | 0.7258 | 0.069* | 0.39 (2) |
C10B | −0.0401 (7) | 0.3148 (9) | 0.6188 (17) | 0.059 (2) | 0.61 (2) |
H10C | −0.0619 | 0.3169 | 0.7501 | 0.071* | 0.61 (2) |
H10D | −0.0487 | 0.2551 | 0.5663 | 0.071* | 0.61 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0700 (3) | 0.1349 (5) | 0.1014 (3) | −0.0016 (2) | −0.0135 (2) | 0.0210 (2) |
O1 | 0.0752 (13) | 0.0818 (16) | 0.0491 (10) | 0.0044 (11) | −0.0026 (9) | 0.0253 (10) |
N1 | 0.0740 (16) | 0.0542 (16) | 0.0373 (11) | 0.0027 (13) | 0.0008 (11) | 0.0120 (11) |
C2 | 0.0742 (19) | 0.0405 (16) | 0.0434 (13) | 0.0007 (14) | −0.0004 (13) | 0.0012 (12) |
C3 | 0.082 (2) | 0.060 (2) | 0.0505 (15) | −0.0032 (17) | 0.0076 (15) | 0.0044 (14) |
C4 | 0.071 (2) | 0.064 (2) | 0.0688 (19) | −0.0054 (17) | 0.0094 (15) | 0.0014 (16) |
C5 | 0.073 (2) | 0.064 (2) | 0.070 (2) | −0.0028 (16) | −0.0075 (17) | 0.0020 (16) |
C6 | 0.074 (2) | 0.062 (2) | 0.0499 (15) | −0.0001 (16) | −0.0078 (14) | 0.0063 (14) |
C7 | 0.0710 (18) | 0.0384 (16) | 0.0417 (13) | −0.0026 (13) | −0.0026 (12) | 0.0030 (11) |
C8 | 0.0729 (18) | 0.0351 (15) | 0.0372 (12) | −0.0008 (13) | −0.0034 (12) | −0.0007 (11) |
C9 | 0.082 (2) | 0.071 (2) | 0.0438 (15) | −0.0037 (18) | −0.0009 (14) | 0.0188 (14) |
C11 | 0.0754 (19) | 0.0448 (17) | 0.0409 (13) | 0.0034 (15) | 0.0012 (12) | 0.0033 (12) |
C12 | 0.0739 (18) | 0.0415 (16) | 0.0363 (12) | 0.0008 (14) | 0.0002 (12) | 0.0021 (11) |
C13 | 0.0715 (18) | 0.0374 (15) | 0.0343 (12) | −0.0006 (13) | 0.0028 (12) | 0.0011 (11) |
C14 | 0.075 (2) | 0.0493 (18) | 0.0510 (15) | 0.0002 (15) | −0.0005 (14) | 0.0049 (13) |
C15 | 0.074 (2) | 0.061 (2) | 0.0544 (16) | −0.0034 (16) | 0.0019 (14) | 0.0079 (14) |
C16 | 0.076 (2) | 0.064 (2) | 0.0621 (18) | −0.0054 (17) | −0.0012 (15) | 0.0070 (15) |
C17 | 0.069 (2) | 0.056 (2) | 0.0716 (19) | −0.0089 (16) | 0.0036 (16) | −0.0021 (16) |
C18 | 0.086 (2) | 0.075 (2) | 0.074 (2) | −0.0008 (19) | 0.0086 (18) | 0.0047 (18) |
C19 | 0.132 (4) | 0.091 (3) | 0.074 (2) | −0.016 (3) | 0.019 (3) | 0.006 (2) |
C20 | 0.105 (4) | 0.130 (4) | 0.105 (3) | −0.033 (3) | 0.037 (3) | −0.021 (3) |
C21 | 0.070 (2) | 0.158 (5) | 0.119 (4) | −0.018 (3) | 0.014 (3) | −0.026 (3) |
C22 | 0.073 (2) | 0.100 (3) | 0.091 (2) | −0.006 (2) | −0.001 (2) | −0.005 (2) |
C10A | 0.084 (7) | 0.049 (10) | 0.041 (6) | 0.023 (8) | 0.017 (5) | 0.013 (5) |
C10B | 0.088 (4) | 0.048 (6) | 0.042 (4) | 0.006 (5) | 0.009 (3) | 0.010 (3) |
Br1—C5 | 1.900 (3) | C11—C10B | 1.532 (11) |
O1—C12 | 1.237 (3) | C11—C10A | 1.529 (16) |
N1—C2 | 1.366 (4) | C12—C13 | 1.435 (4) |
N1—C13 | 1.373 (3) | C14—C15 | 1.432 (4) |
N1—H1 | 0.82 (3) | C14—H14 | 0.9300 |
C2—C3 | 1.386 (4) | C15—C16 | 1.325 (4) |
C2—C7 | 1.415 (4) | C15—H15 | 0.9300 |
C3—C4 | 1.370 (4) | C16—C17 | 1.458 (4) |
C3—H3 | 0.9300 | C16—H16 | 0.9300 |
C4—C5 | 1.406 (4) | C17—C18 | 1.379 (4) |
C4—H4 | 0.9300 | C17—C22 | 1.387 (4) |
C5—C6 | 1.357 (5) | C18—C19 | 1.377 (5) |
C6—C7 | 1.403 (4) | C18—H18 | 0.9300 |
C6—H6 | 0.9300 | C19—C20 | 1.363 (6) |
C7—C8 | 1.413 (4) | C19—H19 | 0.9300 |
C8—C13 | 1.374 (4) | C20—C21 | 1.359 (6) |
C8—C9 | 1.492 (4) | C20—H20 | 0.9300 |
C9—C10A | 1.429 (17) | C21—C22 | 1.366 (5) |
C9—C10B | 1.491 (12) | C21—H21 | 0.9300 |
C9—H9A | 0.9700 | C22—H22 | 0.9300 |
C9—H9B | 0.9700 | C10A—H10A | 0.9700 |
C9—H9C | 0.9700 | C10A—H10B | 0.9700 |
C9—H9D | 0.9700 | C10B—H10C | 0.9700 |
C11—C14 | 1.335 (4) | C10B—H10D | 0.9700 |
C11—C12 | 1.483 (4) | ||
C2—N1—C13 | 108.3 (2) | C14—C11—C10A | 121.7 (6) |
C2—N1—H1 | 123 (2) | C12—C11—C10A | 117.9 (7) |
C13—N1—H1 | 127 (2) | C10B—C11—C10A | 24.7 (5) |
N1—C2—C3 | 129.9 (2) | O1—C12—C13 | 122.0 (2) |
N1—C2—C7 | 108.2 (2) | O1—C12—C11 | 122.5 (3) |
C3—C2—C7 | 121.9 (3) | C13—C12—C11 | 115.5 (2) |
C4—C3—C2 | 117.9 (3) | N1—C13—C8 | 109.8 (2) |
C4—C3—H3 | 121.1 | N1—C13—C12 | 124.6 (2) |
C2—C3—H3 | 121.1 | C8—C13—C12 | 125.6 (2) |
C3—C4—C5 | 120.3 (3) | C11—C14—C15 | 128.3 (3) |
C3—C4—H4 | 119.9 | C11—C14—H14 | 115.8 |
C5—C4—H4 | 119.9 | C15—C14—H14 | 115.8 |
C6—C5—C4 | 122.8 (3) | C16—C15—C14 | 123.3 (3) |
C6—C5—Br1 | 119.5 (2) | C16—C15—H15 | 118.3 |
C4—C5—Br1 | 117.7 (3) | C14—C15—H15 | 118.3 |
C5—C6—C7 | 117.9 (3) | C15—C16—C17 | 128.1 (3) |
C5—C6—H6 | 121.1 | C15—C16—H16 | 116.0 |
C7—C6—H6 | 121.1 | C17—C16—H16 | 116.0 |
C6—C7—C8 | 134.2 (2) | C18—C17—C22 | 117.9 (3) |
C6—C7—C2 | 119.2 (3) | C18—C17—C16 | 122.7 (3) |
C8—C7—C2 | 106.6 (2) | C22—C17—C16 | 119.4 (3) |
C13—C8—C7 | 107.0 (2) | C19—C18—C17 | 120.9 (4) |
C13—C8—C9 | 121.6 (3) | C19—C18—H18 | 119.6 |
C7—C8—C9 | 131.4 (2) | C17—C18—H18 | 119.6 |
C10A—C9—C8 | 115.1 (6) | C20—C19—C18 | 120.1 (4) |
C10A—C9—C10B | 25.8 (6) | C20—C19—H19 | 120.0 |
C8—C9—C10B | 113.2 (4) | C18—C19—H19 | 120.0 |
C10A—C9—H9A | 108.5 | C21—C20—C19 | 119.8 (4) |
C8—C9—H9A | 108.5 | C21—C20—H20 | 120.1 |
C10B—C9—H9A | 85.8 | C19—C20—H20 | 120.1 |
C10A—C9—H9B | 108.5 | C20—C21—C22 | 120.7 (4) |
C8—C9—H9B | 108.5 | C20—C21—H21 | 119.6 |
C10B—C9—H9B | 129.1 | C22—C21—H21 | 119.6 |
H9A—C9—H9B | 107.5 | C21—C22—C17 | 120.7 (4) |
C10A—C9—H9C | 84.7 | C21—C22—H22 | 119.7 |
C8—C9—H9C | 108.9 | C17—C22—H22 | 119.7 |
C10B—C9—H9C | 108.9 | C9—C10A—C11 | 120.7 (9) |
H9A—C9—H9C | 129.3 | C9—C10A—H10A | 107.2 |
H9B—C9—H9C | 27.1 | C11—C10A—H10A | 107.2 |
C10A—C9—H9D | 127.0 | C9—C10A—H10B | 107.2 |
C8—C9—H9D | 108.9 | C11—C10A—H10B | 107.2 |
C10B—C9—H9D | 108.9 | H10A—C10A—H10B | 106.8 |
H9A—C9—H9D | 26.4 | C9—C10B—C11 | 116.5 (7) |
H9B—C9—H9D | 82.8 | C9—C10B—H10C | 108.2 |
H9C—C9—H9D | 107.8 | C11—C10B—H10C | 108.2 |
C14—C11—C12 | 117.9 (2) | C9—C10B—H10D | 108.2 |
C14—C11—C10B | 123.6 (5) | C11—C10B—H10D | 108.2 |
C12—C11—C10B | 117.6 (5) | H10C—C10B—H10D | 107.3 |
C13—N1—C2—C3 | −179.7 (3) | C9—C8—C13—N1 | −178.6 (3) |
C13—N1—C2—C7 | 0.2 (3) | C7—C8—C13—C12 | −179.9 (3) |
N1—C2—C3—C4 | 178.2 (3) | C9—C8—C13—C12 | 0.5 (4) |
C7—C2—C3—C4 | −1.8 (4) | O1—C12—C13—N1 | −2.5 (4) |
C2—C3—C4—C5 | 0.0 (5) | C11—C12—C13—N1 | 177.5 (2) |
C3—C4—C5—C6 | 1.8 (5) | O1—C12—C13—C8 | 178.6 (3) |
C3—C4—C5—Br1 | −176.5 (2) | C11—C12—C13—C8 | −1.5 (4) |
C4—C5—C6—C7 | −1.8 (5) | C12—C11—C14—C15 | −177.5 (3) |
Br1—C5—C6—C7 | 176.6 (2) | C10B—C11—C14—C15 | 13.7 (8) |
C5—C6—C7—C8 | −178.1 (3) | C10A—C11—C14—C15 | −15.7 (12) |
C5—C6—C7—C2 | 0.0 (4) | C11—C14—C15—C16 | 176.1 (3) |
N1—C2—C7—C6 | −178.1 (3) | C14—C15—C16—C17 | −176.8 (3) |
C3—C2—C7—C6 | 1.8 (4) | C15—C16—C17—C18 | 10.0 (6) |
N1—C2—C7—C8 | 0.4 (3) | C15—C16—C17—C22 | −170.7 (4) |
C3—C2—C7—C8 | −179.6 (3) | C22—C17—C18—C19 | 1.9 (5) |
C6—C7—C8—C13 | 177.4 (3) | C16—C17—C18—C19 | −178.8 (3) |
C2—C7—C8—C13 | −0.9 (3) | C17—C18—C19—C20 | −1.3 (6) |
C6—C7—C8—C9 | −3.1 (5) | C18—C19—C20—C21 | 0.3 (7) |
C2—C7—C8—C9 | 178.7 (3) | C19—C20—C21—C22 | 0.1 (8) |
C13—C8—C9—C10A | −10.2 (12) | C20—C21—C22—C17 | 0.6 (7) |
C7—C8—C9—C10A | 170.3 (12) | C18—C17—C22—C21 | −1.5 (6) |
C13—C8—C9—C10B | 18.1 (7) | C16—C17—C22—C21 | 179.2 (4) |
C7—C8—C9—C10B | −161.4 (7) | C8—C9—C10A—C11 | 21 (2) |
C14—C11—C12—O1 | −5.8 (4) | C10B—C9—C10A—C11 | −71 (2) |
C10B—C11—C12—O1 | 163.7 (6) | C14—C11—C10A—C9 | 175.7 (12) |
C10A—C11—C12—O1 | −168.3 (10) | C12—C11—C10A—C9 | −22 (2) |
C14—C11—C12—C13 | 174.2 (3) | C10B—C11—C10A—C9 | 73.4 (19) |
C10B—C11—C12—C13 | −16.3 (7) | C10A—C9—C10B—C11 | 65.1 (18) |
C10A—C11—C12—C13 | 11.7 (11) | C8—C9—C10B—C11 | −34.9 (12) |
C2—N1—C13—C8 | −0.8 (3) | C14—C11—C10B—C9 | −155.8 (6) |
C2—N1—C13—C12 | −179.8 (3) | C12—C11—C10B—C9 | 35.4 (12) |
C7—C8—C13—N1 | 1.0 (3) | C10A—C11—C10B—C9 | −62 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.82 (3) | 2.02 (3) | 2.813 (3) | 161 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C21H16BrNO |
Mr | 378.26 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 17.3682 (7), 14.9974 (8), 6.6861 (3) |
β (°) | 92.226 (2) |
V (Å3) | 1740.27 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 2.37 |
Crystal size (mm) | 0.20 × 0.17 × 0.16 |
Data collection | |
Diffractometer | Bruker SMART APEX CCD detector |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.629, 0.685 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16684, 4319, 2158 |
Rint | 0.044 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.137, 0.97 |
No. of reflections | 4319 |
No. of parameters | 231 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.46, −0.55 |
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 |
N1—H1···O1i | 0.82 (3) | 2.02 (3) | 2.813 (3) | 161 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Acknowledgements
The authors thank the Solid State Unit, Indian Institute of Science, Bangalore, India, for the data collection 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.
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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). Aminocarbazoles are widely used as intermediates for the preparation of carbazole-based synthetic dyes, agrochemicals, pharmaceuticals and light-sensitive materials (Shufen et al., 1995). 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 chemists have been attracted towards these compounds due to their biological activities and potential applications as pharmacological agents (Knolker & Reddy, 2002). 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. One of the C atoms of the cyclohexane ring is disordered with refined occupancies of 0.61 (2) and 0.39 (2). The disordered position of C10B in the cyclohexane ring in the carbazole ring system adopts envelope conformation with the puckering parameters (Cremer & Pople, 1975) and the asymmetry parameters (Nardelli, 1983) are: q2=0.242 (7) Å, q3 = 0.171 (6) Å, φ2 = 117.3 (13)° and Δs(C10B & C13)= 1.5 (5)°. The sum of the bond angles around N1 [358.3°] is in accordance with sp2 hybridization.
The crystal packing reveals that symmetry-related molecules are linked through N—H···O intermolecular hydrogen bonds into cyclic centrosymmetric R22(10) dimers.