2-[(4-Chloro­phen­yl)(2-phenyl-1H-indol-3-yl)meth­yl]cyclo­hexan-1-one

Venkatachalam, M.; Srinivasan, N.; Krishnakumar, R.V.; Chitra, S.; Manisankar, P.

doi:10.1107/S2414314616006441

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 4| April 2016| x160644

doi:10.1107/S2414314616006441

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2-[(4-Chlorophenyl)(2-phenyl-1H-indol-3-yl)methyl]cyclohexan-1-one

M. Venkatachalam,^a N. Srinivasan,^a ^* R. V. Krishnakumar,^a S. Chitra ^b and P. Manisankar ^c

^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

Edited by M. Bolte, Goethe-Universität Frankfurt, Germany (Received 11 April 2016; accepted 16 April 2016; online 22 April 2016)

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

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Chemical scheme

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.

Figure 1
The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.

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.

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Figure 2
Crystal structure of title compound, showing the formation of chains running along the c axis generated by N—H⋯O hydrogen bonds.

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 refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₇H₂₄ClNO
M_r	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 )
T_min, T_max	0.95, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	23418, 4798, 3331
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.40
Computer programs: APEX2 and SAINT-Plus (Bruker, 2009 ), SHELXS2013 (Sheldrick, 2008 ), SHELXL2013 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1474658

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616006441/bt4005sup1.cif

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

checkCIF report

Comment top

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.

Experimental top

Structure description top

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.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: 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).

Figures top

	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.

2-[(4-Chlorophenyl)(2-phenyl-1H-indol-3-yl)methyl]cyclohexan-1-one top

Crystal data top

C₂₇H₂₄ClNO	F(000) = 872
M_r = 413.95	D_x = 1.280 Mg m⁻³ D_m = 1.28 Mg m⁻³ D_m 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

Data collection top

Bruker Kappa APEXII CCD diffractometer	3331 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.034
ω and φ scan	θ_max = 27.2°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −9→9
T_min = 0.95, T_max = 0.96	k = −20→21
23418 measured reflections	l = −23→23
4798 independent reflections

Refinement top

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(F_o²) + (0.0492P)² + 0.6834P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
4798 reflections	Δρ_max = 0.33 e Å⁻³
275 parameters	Δρ_min = −0.40 e Å⁻³

Crystal data top

C₂₇H₂₄ClNO	V = 2147.67 (11) Å³
M_r = 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)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4798 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	3331 reflections with I > 2σ(I)
T_min = 0.95, T_max = 0.96	R_int = 0.034
23418 measured reflections

Refinement top

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	Δρ_max = 0.33 e Å⁻³
4798 reflections	Δρ_min = −0.40 e Å⁻³
275 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.95, 0.96
No. of measured, independent and observed [I > 2σ(I)] reflections	23418, 4798, 3331
R_int	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
Δρ_max, Δρ_min (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 X-ray intensity data collection.

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