organic compounds
2-[(4-Chlorophenyl)(2-phenyl-1H-indol-3-yl)methyl]cyclohexan-1-one
aDepartment of Physics, Thiagarajar College, Madurai 625 009, India, bDepartment of Chemistry, Seethalakshmi Achi College for Women, Pallathur, Karaikudi 630 107, India, and cDepartment of Industrial Chemistry, Alagappa University, Karaikudi 630 003, India
*Correspondence e-mail: vasan692000@yahoo.co.in
In the title compound, C27H24ClNO, the indole ring is almost orthogonal to the chlorophenyl ring and the mean plane of the cyclohexanone ring, making a dihedral angles of 82.11 (6) and 89.96 (4)°, respectively. In the crystal, a strong N—H⋯O hydrogen bond links the molecules, forming chains running along the c axis. The chains are linked by weak C—H⋯π interactions, forming layers parallel to the ac plane.
Keywords: crystal structure; cyclohexanone; antibacterial properties; anticancer activity; hydrogen bonding.
CCDC reference: 1474658
Structure description
Indole is a potent pharmacodynamic nucleus possessing properties such as anti-inflammatory, anti-cancer and antimicrobial activities (George et al., 2008; El-Sawy et al., 2009; Mandour et al., 2007, 2010). Cyclohexanone is an aliphatic cyclic ketone (Fatima, et al., 2014). Cyclohexanone derivatives have potent pharmacological activity in the treatment of broad spectrum of medical conditions (Puetz et al., 2003). The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anaesthetic and antihistaminic drugs (Rajveer et al., 2010; Fatima et al., 2013). Cyclohexanone derivatives penetrate into the stratum corneum and alter the skin permeability of indomethacin by fluidizing or modifying the hard hydrophobic barrier of the corneum (Danyi et al., 1989; Rizwana Begum et al., 2012). Evaluation of bioactivities has shown cyclohexanone-containing analogues to exhibit anti-tumour properties and a wider anti-tumour spectrum than the acetone and cyclopentanone-containing analogues (Chen et al., 2010).
The indole ring in the title compound (Fig. 1) is almost orthogonal to both the chlorophenyl ring and the mean plane of the cyclohexanone rings, making a dihedral angles of 82.11 (6) and 89.96 (4)°, respectively. Similarly the phenyl ring and cyclohexanone mean plane are nearly orthogonal at a dihedral angle of 80.50 (8)°. The chlorophenyl ring is inclined to the phenyl and cyclohexanone rings by 43.57 (9) and 40.66 (9)°, respectively.
In the crystal, a strong N—H⋯O hydrogen bond links the molecules, forming chains running along the c axis (Fig. 2 and Table 1). A weak C10—H10⋯π interaction generates chains running along the a axis. Together, these interactions generate a layered structure.
Synthesis and crystallization
A mixture of 2-(3-oxo-1,3-diarylpropyl)-1-cyclohexanones (1 mmol) and phenylhydrazine hydrochloride (3 mmol) in THF (10 ml) was refluxed for 3–4 h. After completion of the reaction (TLC), the mixture was poured into ice-cold water and the solid separated was filtered off. The product was separated by flash column using petroleum ether and ethylacetate (10:1 v/v) as eluant. The title compound was isolated as colourless plates.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1474658
10.1107/S2414314616006441/bt4005sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616006441/bt4005Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616006441/bt4005Isup3.cdx
Supporting information file. DOI: 10.1107/S2414314616006441/bt4005Isup4.cml
A mixture of 2-(3-oxo-1,3-diarylpropyl)-1-cyclohexanones (1 mmol) and phenylhydrazine hydrochloride (3 mmol) in THF (10 ml) was refluxed for 3–4 h. After completion of the reaction (TLC), the mixture was poured into ice-cold water and the solid separated was filtered off. The product was separated by flash column using petroleum ether and ethylacetate (10:1 v/v) as eluant. The title compound was isolated as colourless plates.
Indole is a potent pharmacodynamic nucleus possessing properties such as anti-inflammatory, anti-cancer and antimicrobial activities (George et al., 2008; El-Sawy et al., 2009; Mandour et al., 2007, 2010). Cyclohexanone is an aliphatic cyclic ketone (Fatima, et al., 2014). Cyclohexanone derivatives have potent pharmacological activity in the treatment of broad spectrum of medical conditions (Puetz et al., 2003). The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anaesthetic and antihistaminic drugs (Rajveer et al., 2010; Fatima et al., 2013). Cyclohexanone derivatives penetrate into the stratum corneum and alter the skin permeability of indomethacin by fluidizing or modifying the hard hydrophobic barrier of the corneum (Danyi et al., 1989; Begum et al., 2012). Evaluation of bioactivities has shown cyclohexanone-containing analogues to exhibit anti-tumour properties and a wider anti-tumour spectrum than the acetone and cyclopentanone-containing analogues (Chen et al., 2010).
The indole ring in the title compound (Fig. 1) is almost orthogonal to both chlorophenyl and cyclohexanone rings, making a dihedral angles of 82.11 (6) and 89.96 (4)°, respectively. Similarly the phenyl ring and cyclohexanone are nearly orthogonal at a dihedral angle of 80.50 (8)°. The chlorophenyl ring is inclined to the phenyl and cyclohexanone rings by 43.57 (9) and 40.66 (9)°, respectively.
In the crystal, a strong N—H···O hydrogen bond links the molecules, forming chains running along the c axis (Fig. 2 and Table 1). A weak C10—H10···π interaction generates chains running along the a axis. Together, these interactions generate a layered structure.
Data collection: APEX2 (Bruker, 2009); cell
SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms. | |
Fig. 2. Crystal structure of title compound, showing the formation of chains running along the c axis generated by N—H···O hydrogen bonds. |
C27H24ClNO | F(000) = 872 |
Mr = 413.95 | Dx = 1.280 Mg m−3 Dm = 1.28 Mg m−3 Dm measured by floatation method |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.2562 (2) Å | Cell parameters from 7435 reflections |
b = 16.4818 (5) Å | θ = 5.0–54.2° |
c = 18.0306 (6) Å | µ = 0.20 mm−1 |
β = 95.149 (2)° | T = 293 K |
V = 2147.67 (11) Å3 | Plate, colourless |
Z = 4 | 0.35 × 0.21 × 0.16 mm |
Bruker Kappa APEXII CCD diffractometer | 3331 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
ω and φ scan | θmax = 27.2°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −9→9 |
Tmin = 0.95, Tmax = 0.96 | k = −20→21 |
23418 measured reflections | l = −23→23 |
4798 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.124 | w = 1/[σ2(Fo2) + (0.0492P)2 + 0.6834P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
4798 reflections | Δρmax = 0.33 e Å−3 |
275 parameters | Δρmin = −0.40 e Å−3 |
C27H24ClNO | V = 2147.67 (11) Å3 |
Mr = 413.95 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.2562 (2) Å | µ = 0.20 mm−1 |
b = 16.4818 (5) Å | T = 293 K |
c = 18.0306 (6) Å | 0.35 × 0.21 × 0.16 mm |
β = 95.149 (2)° |
Bruker Kappa APEXII CCD diffractometer | 4798 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 3331 reflections with I > 2σ(I) |
Tmin = 0.95, Tmax = 0.96 | Rint = 0.034 |
23418 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.124 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.33 e Å−3 |
4798 reflections | Δρmin = −0.40 e Å−3 |
275 parameters |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
H1 | 0.580 (3) | 0.7097 (12) | −0.2067 (12) | 0.055 (6)* | |
Cl1 | 1.35108 (9) | 0.93406 (4) | 0.15842 (4) | 0.0884 (2) | |
O1 | 0.58279 (17) | 0.75702 (7) | 0.18216 (6) | 0.0466 (3) | |
N1 | 0.6256 (2) | 0.69785 (9) | −0.16453 (8) | 0.0438 (4) | |
C1 | 0.7775 (2) | 0.65094 (10) | −0.14730 (9) | 0.0398 (4) | |
C2 | 0.8774 (3) | 0.60370 (11) | −0.19316 (10) | 0.0505 (5) | |
H2 | 0.8459 | 0.6013 | −0.2443 | 0.061* | |
C3 | 1.0239 (3) | 0.56090 (12) | −0.16037 (11) | 0.0579 (5) | |
H3 | 1.0930 | 0.5284 | −0.1897 | 0.069* | |
C4 | 1.0720 (3) | 0.56496 (12) | −0.08374 (11) | 0.0550 (5) | |
H4 | 1.1708 | 0.5342 | −0.0628 | 0.066* | |
C5 | 0.9763 (2) | 0.61330 (11) | −0.03885 (10) | 0.0458 (4) | |
H5 | 1.0111 | 0.6162 | 0.0120 | 0.055* | |
C6 | 0.8261 (2) | 0.65818 (10) | −0.07032 (8) | 0.0376 (4) | |
C7 | 0.6973 (2) | 0.71423 (10) | −0.04213 (8) | 0.0368 (4) | |
C8 | 0.5782 (2) | 0.73760 (10) | −0.10163 (8) | 0.0394 (4) | |
C9 | 0.4177 (2) | 0.79283 (11) | −0.10919 (9) | 0.0429 (4) | |
C10 | 0.2496 (3) | 0.76591 (13) | −0.14256 (11) | 0.0596 (5) | |
H10 | 0.2358 | 0.7115 | −0.1557 | 0.071* | |
C11 | 0.1022 (3) | 0.81797 (17) | −0.15668 (14) | 0.0749 (7) | |
H11 | −0.0099 | 0.7984 | −0.1787 | 0.090* | |
C12 | 0.1199 (3) | 0.89791 (17) | −0.13854 (14) | 0.0764 (7) | |
H12 | 0.0211 | 0.9333 | −0.1490 | 0.092* | |
C13 | 0.2848 (3) | 0.92597 (15) | −0.10471 (15) | 0.0778 (7) | |
H13 | 0.2974 | 0.9804 | −0.0918 | 0.093* | |
C14 | 0.4317 (3) | 0.87357 (13) | −0.08986 (13) | 0.0619 (5) | |
H14 | 0.5422 | 0.8931 | −0.0664 | 0.074* | |
C15 | 0.6874 (2) | 0.73783 (10) | 0.03812 (8) | 0.0365 (4) | |
H15 | 0.5848 | 0.7763 | 0.0393 | 0.044* | |
C16 | 0.8628 (2) | 0.78262 (10) | 0.06868 (8) | 0.0383 (4) | |
C17 | 0.9042 (3) | 0.85589 (14) | 0.03785 (13) | 0.0743 (7) | |
H17 | 0.8278 | 0.8754 | −0.0023 | 0.089* | |
C18 | 1.0548 (4) | 0.90128 (14) | 0.06438 (14) | 0.0794 (7) | |
H18 | 1.0792 | 0.9506 | 0.0421 | 0.095* | |
C19 | 1.1670 (3) | 0.87422 (12) | 0.12271 (11) | 0.0517 (5) | |
C20 | 1.1358 (3) | 0.80067 (13) | 0.15377 (12) | 0.0591 (5) | |
H20 | 1.2154 | 0.7810 | 0.1930 | 0.071* | |
C21 | 0.9837 (3) | 0.75567 (12) | 0.12616 (11) | 0.0527 (5) | |
H21 | 0.9629 | 0.7054 | 0.1474 | 0.063* | |
C22 | 0.6399 (2) | 0.66461 (10) | 0.08515 (8) | 0.0370 (4) | |
H22 | 0.7441 | 0.6266 | 0.0876 | 0.044* | |
C23 | 0.6033 (2) | 0.68732 (11) | 0.16372 (8) | 0.0386 (4) | |
C24 | 0.5736 (3) | 0.61723 (12) | 0.21343 (10) | 0.0563 (5) | |
H24A | 0.5551 | 0.6364 | 0.2631 | 0.068* | |
H24B | 0.6810 | 0.5819 | 0.2167 | 0.068* | |
C25 | 0.4033 (3) | 0.57094 (13) | 0.18092 (11) | 0.0625 (6) | |
H25A | 0.3876 | 0.5226 | 0.2103 | 0.075* | |
H25B | 0.2944 | 0.6046 | 0.1834 | 0.075* | |
C26 | 0.4211 (3) | 0.54718 (12) | 0.10116 (11) | 0.0574 (5) | |
H26A | 0.3064 | 0.5225 | 0.0807 | 0.069* | |
H26B | 0.5187 | 0.5071 | 0.0997 | 0.069* | |
C27 | 0.4647 (3) | 0.61950 (12) | 0.05341 (10) | 0.0518 (5) | |
H27A | 0.3607 | 0.6567 | 0.0502 | 0.062* | |
H27B | 0.4816 | 0.6009 | 0.0034 | 0.062* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0660 (4) | 0.0675 (4) | 0.1272 (6) | −0.0240 (3) | −0.0165 (4) | −0.0153 (4) |
O1 | 0.0624 (8) | 0.0458 (7) | 0.0319 (6) | −0.0011 (6) | 0.0062 (5) | −0.0077 (5) |
N1 | 0.0591 (9) | 0.0482 (9) | 0.0237 (7) | −0.0008 (7) | 0.0005 (6) | 0.0018 (6) |
C1 | 0.0506 (10) | 0.0387 (9) | 0.0307 (8) | −0.0074 (8) | 0.0069 (7) | 0.0010 (7) |
C2 | 0.0677 (12) | 0.0499 (11) | 0.0353 (9) | −0.0063 (9) | 0.0128 (8) | −0.0064 (8) |
C3 | 0.0654 (13) | 0.0538 (12) | 0.0576 (12) | 0.0015 (10) | 0.0234 (10) | −0.0109 (10) |
C4 | 0.0514 (11) | 0.0553 (12) | 0.0587 (12) | 0.0054 (9) | 0.0073 (9) | −0.0003 (9) |
C5 | 0.0468 (10) | 0.0523 (11) | 0.0381 (9) | −0.0023 (8) | 0.0033 (7) | 0.0016 (8) |
C6 | 0.0446 (9) | 0.0386 (9) | 0.0299 (8) | −0.0075 (7) | 0.0053 (7) | 0.0006 (7) |
C7 | 0.0425 (9) | 0.0410 (9) | 0.0271 (8) | −0.0068 (7) | 0.0042 (6) | 0.0002 (7) |
C8 | 0.0498 (10) | 0.0403 (9) | 0.0282 (8) | −0.0065 (7) | 0.0034 (7) | 0.0009 (7) |
C9 | 0.0487 (10) | 0.0483 (11) | 0.0318 (8) | −0.0021 (8) | 0.0051 (7) | 0.0049 (7) |
C10 | 0.0588 (12) | 0.0553 (12) | 0.0621 (13) | −0.0078 (10) | −0.0080 (10) | 0.0063 (10) |
C11 | 0.0508 (13) | 0.0830 (18) | 0.0882 (17) | −0.0032 (12) | −0.0088 (11) | 0.0132 (14) |
C12 | 0.0561 (14) | 0.0830 (19) | 0.0900 (18) | 0.0166 (12) | 0.0053 (12) | 0.0087 (14) |
C13 | 0.0704 (16) | 0.0594 (14) | 0.1039 (19) | 0.0119 (12) | 0.0094 (14) | −0.0124 (13) |
C14 | 0.0535 (11) | 0.0577 (13) | 0.0736 (14) | 0.0011 (10) | 0.0014 (10) | −0.0126 (11) |
C15 | 0.0424 (9) | 0.0398 (9) | 0.0273 (8) | −0.0034 (7) | 0.0027 (6) | −0.0036 (6) |
C16 | 0.0460 (9) | 0.0407 (9) | 0.0285 (8) | −0.0052 (7) | 0.0049 (7) | −0.0046 (7) |
C17 | 0.0902 (16) | 0.0610 (14) | 0.0652 (14) | −0.0272 (12) | −0.0300 (12) | 0.0218 (11) |
C18 | 0.0933 (17) | 0.0548 (14) | 0.0851 (17) | −0.0304 (13) | −0.0195 (14) | 0.0184 (12) |
C19 | 0.0461 (10) | 0.0468 (11) | 0.0617 (12) | −0.0102 (8) | 0.0015 (9) | −0.0111 (9) |
C20 | 0.0454 (11) | 0.0623 (13) | 0.0670 (13) | −0.0062 (9) | −0.0102 (9) | 0.0063 (10) |
C21 | 0.0463 (10) | 0.0480 (11) | 0.0619 (12) | −0.0083 (8) | −0.0051 (9) | 0.0099 (9) |
C22 | 0.0422 (9) | 0.0410 (9) | 0.0284 (8) | −0.0047 (7) | 0.0065 (6) | −0.0045 (7) |
C23 | 0.0398 (9) | 0.0467 (10) | 0.0290 (8) | −0.0042 (7) | 0.0016 (6) | −0.0044 (7) |
C24 | 0.0831 (14) | 0.0526 (12) | 0.0344 (9) | −0.0065 (10) | 0.0122 (9) | 0.0017 (8) |
C25 | 0.0803 (15) | 0.0550 (13) | 0.0557 (12) | −0.0161 (11) | 0.0247 (11) | 0.0027 (10) |
C26 | 0.0618 (12) | 0.0548 (12) | 0.0564 (12) | −0.0208 (10) | 0.0100 (9) | −0.0078 (9) |
C27 | 0.0586 (11) | 0.0599 (12) | 0.0369 (9) | −0.0214 (9) | 0.0039 (8) | −0.0082 (8) |
Cl1—C19 | 1.7367 (18) | C14—H14 | 0.9300 |
O1—C23 | 1.209 (2) | C15—C16 | 1.531 (2) |
N1—C1 | 1.359 (2) | C15—C22 | 1.532 (2) |
N1—C8 | 1.380 (2) | C15—H15 | 0.9800 |
N1—H1 | 0.82 (2) | C16—C21 | 1.371 (2) |
C1—C2 | 1.387 (2) | C16—C17 | 1.374 (3) |
C1—C6 | 1.406 (2) | C17—C18 | 1.374 (3) |
C2—C3 | 1.365 (3) | C17—H17 | 0.9300 |
C2—H2 | 0.9300 | C18—C19 | 1.347 (3) |
C3—C4 | 1.396 (3) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.363 (3) |
C4—C5 | 1.368 (3) | C20—C21 | 1.384 (3) |
C4—H4 | 0.9300 | C20—H20 | 0.9300 |
C5—C6 | 1.395 (2) | C21—H21 | 0.9300 |
C5—H5 | 0.9300 | C22—C23 | 1.511 (2) |
C6—C7 | 1.439 (2) | C22—C27 | 1.538 (2) |
C7—C8 | 1.371 (2) | C22—H22 | 0.9800 |
C7—C15 | 1.506 (2) | C23—C24 | 1.490 (2) |
C8—C9 | 1.475 (2) | C24—C25 | 1.524 (3) |
C9—C14 | 1.377 (3) | C24—H24A | 0.9700 |
C9—C10 | 1.384 (3) | C24—H24B | 0.9700 |
C10—C11 | 1.377 (3) | C25—C26 | 1.507 (3) |
C10—H10 | 0.9300 | C25—H25A | 0.9700 |
C11—C12 | 1.361 (4) | C25—H25B | 0.9700 |
C11—H11 | 0.9300 | C26—C27 | 1.520 (3) |
C12—C13 | 1.374 (3) | C26—H26A | 0.9700 |
C12—H12 | 0.9300 | C26—H26B | 0.9700 |
C13—C14 | 1.379 (3) | C27—H27A | 0.9700 |
C13—H13 | 0.9300 | C27—H27B | 0.9700 |
C1—N1—C8 | 109.83 (14) | C21—C16—C17 | 116.25 (17) |
C1—N1—H1 | 126.5 (14) | C21—C16—C15 | 124.84 (15) |
C8—N1—H1 | 122.5 (14) | C17—C16—C15 | 118.91 (16) |
N1—C1—C2 | 129.78 (16) | C16—C17—C18 | 122.3 (2) |
N1—C1—C6 | 107.69 (14) | C16—C17—H17 | 118.9 |
C2—C1—C6 | 122.53 (17) | C18—C17—H17 | 118.9 |
C3—C2—C1 | 117.42 (17) | C19—C18—C17 | 119.8 (2) |
C3—C2—H2 | 121.3 | C19—C18—H18 | 120.1 |
C1—C2—H2 | 121.3 | C17—C18—H18 | 120.1 |
C2—C3—C4 | 121.29 (17) | C18—C19—C20 | 120.27 (18) |
C2—C3—H3 | 119.4 | C18—C19—Cl1 | 119.48 (16) |
C4—C3—H3 | 119.4 | C20—C19—Cl1 | 120.24 (16) |
C5—C4—C3 | 121.23 (19) | C19—C20—C21 | 119.04 (19) |
C5—C4—H4 | 119.4 | C19—C20—H20 | 120.5 |
C3—C4—H4 | 119.4 | C21—C20—H20 | 120.5 |
C4—C5—C6 | 119.18 (17) | C16—C21—C20 | 122.27 (18) |
C4—C5—H5 | 120.4 | C16—C21—H21 | 118.9 |
C6—C5—H5 | 120.4 | C20—C21—H21 | 118.9 |
C5—C6—C1 | 118.30 (15) | C23—C22—C15 | 113.00 (13) |
C5—C6—C7 | 134.86 (15) | C23—C22—C27 | 105.06 (13) |
C1—C6—C7 | 106.84 (14) | C15—C22—C27 | 113.23 (14) |
C8—C7—C6 | 106.73 (14) | C23—C22—H22 | 108.5 |
C8—C7—C15 | 126.73 (15) | C15—C22—H22 | 108.5 |
C6—C7—C15 | 126.41 (14) | C27—C22—H22 | 108.5 |
C7—C8—N1 | 108.87 (15) | O1—C23—C24 | 122.91 (15) |
C7—C8—C9 | 133.06 (15) | O1—C23—C22 | 121.97 (15) |
N1—C8—C9 | 118.06 (14) | C24—C23—C22 | 114.76 (15) |
C14—C9—C10 | 117.52 (18) | C23—C24—C25 | 108.23 (16) |
C14—C9—C8 | 122.23 (16) | C23—C24—H24A | 110.1 |
C10—C9—C8 | 120.02 (17) | C25—C24—H24A | 110.1 |
C11—C10—C9 | 121.3 (2) | C23—C24—H24B | 110.1 |
C11—C10—H10 | 119.3 | C25—C24—H24B | 110.1 |
C9—C10—H10 | 119.3 | H24A—C24—H24B | 108.4 |
C12—C11—C10 | 120.3 (2) | C26—C25—C24 | 111.16 (15) |
C12—C11—H11 | 119.9 | C26—C25—H25A | 109.4 |
C10—C11—H11 | 119.9 | C24—C25—H25A | 109.4 |
C11—C12—C13 | 119.5 (2) | C26—C25—H25B | 109.4 |
C11—C12—H12 | 120.3 | C24—C25—H25B | 109.4 |
C13—C12—H12 | 120.3 | H25A—C25—H25B | 108.0 |
C12—C13—C14 | 120.2 (2) | C25—C26—C27 | 112.13 (16) |
C12—C13—H13 | 119.9 | C25—C26—H26A | 109.2 |
C14—C13—H13 | 119.9 | C27—C26—H26A | 109.2 |
C9—C14—C13 | 121.2 (2) | C25—C26—H26B | 109.2 |
C9—C14—H14 | 119.4 | C27—C26—H26B | 109.2 |
C13—C14—H14 | 119.4 | H26A—C26—H26B | 107.9 |
C7—C15—C16 | 111.14 (12) | C26—C27—C22 | 112.04 (15) |
C7—C15—C22 | 111.15 (13) | C26—C27—H27A | 109.2 |
C16—C15—C22 | 113.70 (13) | C22—C27—H27A | 109.2 |
C7—C15—H15 | 106.8 | C26—C27—H27B | 109.2 |
C16—C15—H15 | 106.8 | C22—C27—H27B | 109.2 |
C22—C15—H15 | 106.8 | H27A—C27—H27B | 107.9 |
C8—N1—C1—C2 | −176.83 (17) | C12—C13—C14—C9 | 0.8 (4) |
C8—N1—C1—C6 | 2.17 (19) | C8—C7—C15—C16 | −120.19 (18) |
N1—C1—C2—C3 | −178.67 (18) | C6—C7—C15—C16 | 64.5 (2) |
C6—C1—C2—C3 | 2.5 (3) | C8—C7—C15—C22 | 112.10 (18) |
C1—C2—C3—C4 | −0.4 (3) | C6—C7—C15—C22 | −63.2 (2) |
C2—C3—C4—C5 | −1.4 (3) | C7—C15—C16—C21 | −117.57 (19) |
C3—C4—C5—C6 | 1.1 (3) | C22—C15—C16—C21 | 8.7 (2) |
C4—C5—C6—C1 | 0.8 (2) | C7—C15—C16—C17 | 63.3 (2) |
C4—C5—C6—C7 | −179.46 (18) | C22—C15—C16—C17 | −170.40 (18) |
N1—C1—C6—C5 | 178.23 (15) | C21—C16—C17—C18 | −2.1 (4) |
C2—C1—C6—C5 | −2.7 (2) | C15—C16—C17—C18 | 177.1 (2) |
N1—C1—C6—C7 | −1.56 (18) | C16—C17—C18—C19 | −0.2 (4) |
C2—C1—C6—C7 | 177.53 (15) | C17—C18—C19—C20 | 2.4 (4) |
C5—C6—C7—C8 | −179.35 (18) | C17—C18—C19—Cl1 | −177.2 (2) |
C1—C6—C7—C8 | 0.40 (18) | C18—C19—C20—C21 | −2.2 (3) |
C5—C6—C7—C15 | −3.3 (3) | Cl1—C19—C20—C21 | 177.40 (16) |
C1—C6—C7—C15 | 176.45 (15) | C17—C16—C21—C20 | 2.3 (3) |
C6—C7—C8—N1 | 0.90 (18) | C15—C16—C21—C20 | −176.89 (17) |
C15—C7—C8—N1 | −175.13 (15) | C19—C20—C21—C16 | −0.2 (3) |
C6—C7—C8—C9 | 179.73 (17) | C7—C15—C22—C23 | −172.32 (13) |
C15—C7—C8—C9 | 3.7 (3) | C16—C15—C22—C23 | 61.37 (18) |
C1—N1—C8—C7 | −1.94 (19) | C7—C15—C22—C27 | −53.01 (19) |
C1—N1—C8—C9 | 179.03 (14) | C16—C15—C22—C27 | −179.32 (14) |
C7—C8—C9—C14 | 59.1 (3) | C15—C22—C23—O1 | 12.0 (2) |
N1—C8—C9—C14 | −122.20 (19) | C27—C22—C23—O1 | −111.93 (18) |
C7—C8—C9—C10 | −126.7 (2) | C15—C22—C23—C24 | −174.64 (15) |
N1—C8—C9—C10 | 52.1 (2) | C27—C22—C23—C24 | 61.44 (19) |
C14—C9—C10—C11 | 0.7 (3) | O1—C23—C24—C25 | 111.76 (19) |
C8—C9—C10—C11 | −173.87 (19) | C22—C23—C24—C25 | −61.5 (2) |
C9—C10—C11—C12 | 0.6 (4) | C23—C24—C25—C26 | 54.5 (2) |
C10—C11—C12—C13 | −1.3 (4) | C24—C25—C26—C27 | −53.6 (2) |
C11—C12—C13—C14 | 0.6 (4) | C25—C26—C27—C22 | 55.8 (2) |
C10—C9—C14—C13 | −1.4 (3) | C23—C22—C27—C26 | −56.3 (2) |
C8—C9—C14—C13 | 173.03 (19) | C15—C22—C27—C26 | 179.95 (15) |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (2) | 2.08 (2) | 2.8525 (18) | 156 (2) |
C10—H10···Cgii | 0.93 | 2.96 | 3.562 (2) | 124 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z. |
Cg is the centroid of the C1–C6 ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.83 (2) | 2.08 (2) | 2.8525 (18) | 156 (2) |
C10—H10···Cgii | 0.93 | 2.96 | 3.562 (2) | 124 |
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C27H24ClNO |
Mr | 413.95 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 7.2562 (2), 16.4818 (5), 18.0306 (6) |
β (°) | 95.149 (2) |
V (Å3) | 2147.67 (11) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.35 × 0.21 × 0.16 |
Data collection | |
Diffractometer | Bruker Kappa APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.95, 0.96 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23418, 4798, 3331 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.644 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.124, 1.04 |
No. of reflections | 4798 |
No. of parameters | 275 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.33, −0.40 |
Computer programs: APEX2 (Bruker, 2009), SAINT-Plus (Bruker, 2009), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), PLATON (Spek, 2009), publCIF (Westrip, 2010).
Acknowledgements
The authors thank Dr Babu Varghese, Scientist, Sophisticated Analytical Instrumentation Facility (SAIF), Indian Institute of Technology, Chennai, for the
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Indole is a potent pharmacodynamic nucleus possessing properties such as anti-inflammatory, anti-cancer and antimicrobial activities (George et al.,2008; El-Sawy et al., 2009; Mandour et al., 2007,2010). Cyclohexanone is an aliphatic cyclic ketone (Fatima, et al., 2014). Cyclohexanone derivatives have potent pharmacological activity in the treatment of broad spectrum of medical conditions (Puetz et al., 2003). The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anesthetic and antihistaminic drugs (Rajveer et al., 2010; Fatima et al., 2013). Cyclohexanone derivatives penetrate into the stratum corneum and alter the skin permeability of indomethacin by fluidizing or modifying the hard hydrophobic barrier of the corneum (Danyi et al., 1989; Begum, et al., 2012). Evaluation of bioactivities show the cyclohexanone-containing analogues exhibited anti-tumour properties and a wider anti-tumour spectrum than the acetone and cyclopentanone-containing analogues (Chen, et al., 2010).
The indole ring is almost orthogonal to both chlorophenyl and cyclohexanone ring systems, making a dihedral angles 82.11 (6)° and 89.96 (4)° respectively. Similarly the phenyl ring and cyclohexanone are nearly orthogonal with dihedral angles of 80.50 (8)°. The chlorophenyl ring is inclined by 43.57 (9)° and 40.66 (9)° with phenyl and cyclohexanone rings respectively. In the structure, a strong N—H···O hydrogen bond links the symmetry equivalent molecules by forming one-dimensional chain running along c-axis.
A weak C10—H10···cg (-1+x, y, z), cg being the centroid of six-membered ring of indole system defined by C1—C6 having a H···cg distance of 2.96 Å and angle of 124°, which generates chain running along a-axis.