Crystal structure of 2,4-bis­(2-chloro­phen­yl)-7-tert-pent­yl-3-aza­bicyclo[3.3.1]nonan-9-one

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S160053681402176X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1161-o1162

doi:10.1107/S160053681402176X

Open

access

Crystal structure of 2,4-bis(2-chlorophenyl)-7-tert-pentyl-3-azabicyclo[3.3.1]nonan-9-one

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a,^c ^*

^aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, ^bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India, and ^cDepartment of Chemistry, VEL TECH, Avadi, Chennai 600 062, India
^*Correspondence e-mail: parthisivam@yahoo.co.in

Edited by V. V. Chernyshev, Moscow State University, Russia (Received 31 August 2014; accepted 2 October 2014; online 15 October 2014)

The title compound, C₂₅H₂₉Cl₂NO, which is a chloro analog of 2,4-bis(2-bromophenyl)-7-(tert-pentyl)-3-azabicyclo[3.3.1]nonan-9-one [Park, Ramkumar & Parthiban (2012). Acta Cryst. E68, o2946], exists in a twin-chair conformation with an equatorial orientation of the 2-chlorophenyl groups. The tert-pentyl group on the cyclohexanone adopts an exocyclic equatorial position and is disordered between two orientations in a ratio 0.520 (8):0.480 (8). The crystal packing shows no directional contacts beyond van der Waals contacts.

Keywords: crystal structure; twin-chair conformation; Mannich base; azabicycle.

CCDC reference: 1027325

1. Related literature

For the synthesis, stereochemistry and biological activity of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011 , 2012a ). For a related crystal structure, see: Park et al. (2012b ). For the conformation of functionalized 3-azabicycles, see: Parthiban et al. (2010 ); Park et al. (2012c ); Padegimas & Kovacic (1972 ).

2. Experimental

2.1. Crystal data

C₂₅H₂₉Cl₂NO
M_r = 430.39
Triclinic, $[P \overline 1]$
a = 7.6006 (3) Å
b = 10.6240 (5) Å
c = 15.1124 (7) Å
α = 106.116 (2)°
β = 99.996 (2)°
γ = 98.266 (2)°
V = 1130.54 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.30 mm⁻¹
T = 298 K
0.25 × 0.20 × 0.15 mm

2.2. Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.928, T_max = 0.955
13160 measured reflections
3789 independent reflections
2944 reflections with I > 2σ(I)
R_int = 0.020

2.3. Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.119
S = 1.03
3789 reflections
313 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL2013.

Supporting information

CCDC reference: 1027325

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681402176X/cv5472sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681402176X/cv5472Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681402176X/cv5472Isup3.cml

checkCIF report

Comment top

Three major conformations, viz., chair-chair (Parthiban et al., 2010), chair-boat (Park et al., 2012c), and boat-boat (Padegimas & Kovacic, 1972) are possible for the bicycle. Hence, the present study is to investigate the stereochemistry of the title compound.

The detailed analysis of asymmetry parameters and torsion angles of the title compound reveal that the values are very similar to its bromo analog. The torsion angles of the title compound C5—C6—C8—C2, C3—C2—C8—C6, C7—C6—C8—C2 and C1—C2—C8—C6 are 63.0 (2), -63.0 (2), -62.6 (2) and 62.4 (2)°, respectively. These values indicate the slightly distorted chair conformation for both six-membered cycles of the fused bicycle.

The orientation of the chlorophenyl groups on both sides of the secondary amino group is identified as equatorial by their torsion angles. The torsion angle of C15—C7—C6—C8 and C8—C2—C1—C9 are 179.99 (17) and -179.01 (17)°, respectively. The orientation of tert-pentyl group on the cyclohexanone ring is also identified as equatorial by the following torsion angles: C21—C4—C5—C6 and C21—C4—C3—C2 are 172.3 (9) and -172.6 (12)°, respectively [C21A—C4—C5—C6 and C21A—C4—C3—C2 are 173.7 (10) and -172.9 (11)°, respectively].

The chloro substituted benzene rings of the title compound is oriented very similar to that of its bromo analog. The benzene rings are inclined to each other with an angle of 29.38°, where as the orientation of bromo analog is 29.6 (3)°.

Based on the complete crystallographic analysis, it is concluded that the title compound, C₂₅H₂₉Cl₂NO, exists in a twin-chair conformation with an equatorial orientation of the 2-chlorophenyl groups.

Related literature top

For the synthesis, stereochemistry and biological activity of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011, 2012a). For a related crystal structure, see: Park et al. (2012b). For the conformation of functionalized 3-azabicycles, see: Parthiban et al. (2010); Park et al. (2012c); Padegimas & Kovacic (1972).

Experimental top

2,4-Bis(2-chlorophenyl)-7-(tert-pentyl)-3-azabicyclo[3.3.1]nonan-9-one was synthesized by a modified and an optimized Mannich condensation in one-pot, using 2-chlorobenzaldehyde (0.1 mol, 14.06 g/11.25 ml), 4-tert-pentylcyclohexanone (0.05 mol, 8.41 g/9.15 ml) and ammonium acetate (0.075 mol, 5.78 g) in a 50 ml of absolute ethanol (Park et al., 2011). The mixture was gently warmed on a hot plate at 303–308 K (30–35° C) with moderate stirring till the complete consumption of the starting materials, which was monitored by TLC. At the end, the crude azabicyclic ketone was separated by filtration and gently washed with 1:5 cold ethanol-ether mixture. X-ray diffraction quality crystals of the title compound were obtained by slow evaporation from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

Figure 1. View of the title molecule showing the atomic numbering and 30% probability displacement ellipsoids. For clarity, only major component of the disordered group is shown.

2,4-Bis(2-chlorophenyl)-7-tert-pentyl-3-azabicyclo[3.3.1]nonan-9-one top

Crystal data top

C₂₅H₂₉Cl₂NO	V = 1130.54 (9) Å³
M_r = 430.39	Z = 2
Triclinic, P1	F(000) = 456
a = 7.6006 (3) Å	D_x = 1.264 Mg m⁻³
b = 10.6240 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 15.1124 (7) Å	µ = 0.30 mm⁻¹
α = 106.116 (2)°	T = 298 K
β = 99.996 (2)°	Block, colourless
γ = 98.266 (2)°	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII area-detector diffractometer	2944 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.020
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θ_max = 25.0°, θ_min = 2.0°
T_min = 0.928, T_max = 0.955	h = −9→6
13160 measured reflections	k = −12→12
3789 independent reflections	l = −17→17

Refinement top

Refinement on F²	13 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0537P)² + 0.5471P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.041
3789 reflections	Δρ_max = 0.36 e Å⁻³
313 parameters	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₅H₂₉Cl₂NO	γ = 98.266 (2)°
M_r = 430.39	V = 1130.54 (9) Å³
Triclinic, P1	Z = 2
a = 7.6006 (3) Å	Mo Kα radiation
b = 10.6240 (5) Å	µ = 0.30 mm⁻¹
c = 15.1124 (7) Å	T = 298 K
α = 106.116 (2)°	0.25 × 0.20 × 0.15 mm
β = 99.996 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	3789 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2944 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.955	R_int = 0.020
13160 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	13 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.36 e Å⁻³
3789 reflections	Δρ_min = −0.27 e Å⁻³
313 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3313 (3)	0.57407 (19)	0.12669 (15)	0.0406 (5)
H1	0.2254	0.5266	0.0749	0.049*
C2	0.2630 (3)	0.6552 (2)	0.21189 (16)	0.0442 (5)
H2	0.1886	0.7138	0.1906	0.053*
C3	0.4123 (3)	0.7409 (2)	0.29862 (15)	0.0468 (5)
H3A	0.4952	0.8002	0.2787	0.056*
H3B	0.3556	0.7964	0.3432	0.056*
C4	0.5240 (3)	0.6624 (2)	0.35002 (16)	0.0466 (5)
H4	0.6008	0.6236	0.3083	0.056*
C5	0.3990 (3)	0.5446 (2)	0.36240 (16)	0.0486 (6)
H5A	0.3413	0.5789	0.4140	0.058*
H5B	0.4737	0.4851	0.3804	0.058*
C6	0.2491 (3)	0.4627 (2)	0.27445 (16)	0.0471 (5)
H6	0.1661	0.3997	0.2925	0.057*
C7	0.3167 (3)	0.38288 (19)	0.18868 (15)	0.0428 (5)
H7	0.2097	0.3330	0.1382	0.051*
C8	0.1434 (3)	0.5563 (2)	0.24180 (16)	0.0488 (6)
C9	0.4562 (3)	0.66577 (19)	0.09259 (14)	0.0380 (5)
C10	0.6447 (3)	0.6856 (2)	0.12042 (16)	0.0465 (5)
H10	0.6951	0.6381	0.1580	0.056*
C11	0.7590 (3)	0.7744 (2)	0.09362 (18)	0.0562 (6)
H11	0.8847	0.7862	0.1138	0.067*
C12	0.6891 (4)	0.8452 (2)	0.03757 (17)	0.0573 (6)
H12	0.7669	0.9052	0.0201	0.069*
C13	0.5037 (3)	0.8269 (2)	0.00741 (15)	0.0494 (6)
H13	0.4550	0.8737	−0.0312	0.059*
C14	0.3896 (3)	0.7384 (2)	0.03483 (14)	0.0419 (5)
C15	0.4261 (3)	0.28405 (19)	0.21254 (15)	0.0425 (5)
C16	0.3442 (3)	0.1555 (2)	0.20782 (16)	0.0488 (6)
C17	0.4439 (4)	0.0637 (2)	0.22588 (19)	0.0623 (7)
H17	0.3849	−0.0216	0.2213	0.075*
C18	0.6297 (4)	0.0981 (3)	0.2506 (2)	0.0695 (8)
H18	0.6979	0.0362	0.2625	0.083*
C19	0.7157 (4)	0.2251 (3)	0.2577 (2)	0.0665 (7)
H19	0.8423	0.2494	0.2755	0.080*
C20	0.6147 (3)	0.3163 (2)	0.23847 (17)	0.0532 (6)
H20	0.6748	0.4013	0.2430	0.064*
C21	0.647 (3)	0.7469 (17)	0.4380 (15)	0.072 (6)	0.520 (8)
C22	0.753 (3)	0.8725 (19)	0.4286 (14)	0.124 (8)	0.520 (8)
H22A	0.7762	0.8544	0.3663	0.186*	0.520 (8)
H22B	0.8667	0.9015	0.4745	0.186*	0.520 (8)
H22C	0.6831	0.9416	0.4389	0.186*	0.520 (8)
C23	0.565 (3)	0.805 (3)	0.5161 (11)	0.105 (7)	0.520 (8)
H23A	0.6564	0.8702	0.5660	0.157*	0.520 (8)
H23B	0.5143	0.7356	0.5393	0.157*	0.520 (8)
H23C	0.4701	0.8471	0.4944	0.157*	0.520 (8)
C24	0.777 (3)	0.668 (2)	0.4817 (17)	0.171 (5)	0.520 (8)
H24A	0.7085	0.6296	0.5198	0.205*	0.520 (8)
H24B	0.7801	0.5927	0.4283	0.205*	0.520 (8)
C25	0.9450 (13)	0.7029 (12)	0.5319 (9)	0.171 (5)	0.520 (8)
H25A	1.0225	0.7434	0.4993	0.256*	0.520 (8)
H25B	0.9861	0.6252	0.5413	0.256*	0.520 (8)
H25C	0.9494	0.7659	0.5922	0.256*	0.520 (8)
C21A	0.665 (4)	0.754 (2)	0.4492 (15)	0.076 (6)	0.480 (8)
C22A	0.799 (2)	0.6604 (15)	0.4763 (10)	0.142 (8)	0.480 (8)
H22D	0.8658	0.7005	0.5407	0.212*	0.480 (8)
H22E	0.8830	0.6503	0.4353	0.212*	0.480 (8)
H22F	0.7287	0.5741	0.4692	0.212*	0.480 (8)
C23A	0.544 (4)	0.820 (3)	0.5231 (16)	0.136 (10)	0.480 (8)
H23D	0.4741	0.8750	0.4969	0.204*	0.480 (8)
H23E	0.6245	0.8743	0.5820	0.204*	0.480 (8)
H23F	0.4636	0.7503	0.5335	0.204*	0.480 (8)
C24A	0.784 (3)	0.8687 (16)	0.4277 (14)	0.084 (5)	0.480 (8)
H24C	0.7014	0.9185	0.4028	0.101*	0.480 (8)
H24D	0.8568	0.9285	0.4879	0.101*	0.480 (8)
C25A	0.8920 (15)	0.8455 (10)	0.3726 (7)	0.128 (4)	0.480 (8)
H25D	0.9835	0.8035	0.3980	0.192*	0.480 (8)
H25E	0.9496	0.9282	0.3664	0.192*	0.480 (8)
H25F	0.8247	0.7873	0.3116	0.192*	0.480 (8)
Cl2	0.10719 (9)	0.10441 (6)	0.17580 (6)	0.0745 (2)
Cl1	0.15563 (9)	0.72003 (8)	−0.00583 (5)	0.0713 (2)
N1	0.4263 (2)	0.47552 (17)	0.15359 (13)	0.0433 (4)
O1	−0.0167 (2)	0.55371 (18)	0.24000 (15)	0.0717 (5)
H1N	0.461 (3)	0.428 (2)	0.1038 (17)	0.054 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0404 (11)	0.0351 (10)	0.0469 (12)	0.0060 (9)	0.0096 (9)	0.0147 (9)
C2	0.0461 (12)	0.0391 (11)	0.0580 (13)	0.0172 (10)	0.0191 (10)	0.0231 (10)
C3	0.0616 (14)	0.0324 (10)	0.0516 (13)	0.0109 (10)	0.0202 (11)	0.0157 (10)
C4	0.0573 (14)	0.0387 (11)	0.0478 (13)	0.0085 (10)	0.0142 (11)	0.0192 (10)
C5	0.0654 (15)	0.0404 (11)	0.0503 (13)	0.0143 (11)	0.0229 (11)	0.0224 (10)
C6	0.0508 (13)	0.0365 (11)	0.0656 (14)	0.0079 (10)	0.0296 (11)	0.0245 (10)
C7	0.0455 (12)	0.0306 (10)	0.0536 (13)	0.0040 (9)	0.0142 (10)	0.0151 (9)
C8	0.0461 (14)	0.0454 (12)	0.0600 (14)	0.0121 (10)	0.0226 (11)	0.0168 (11)
C9	0.0432 (12)	0.0318 (10)	0.0406 (11)	0.0083 (9)	0.0120 (9)	0.0119 (9)
C10	0.0440 (13)	0.0477 (12)	0.0535 (13)	0.0115 (10)	0.0130 (10)	0.0226 (10)
C11	0.0452 (13)	0.0586 (14)	0.0659 (15)	0.0032 (11)	0.0173 (12)	0.0217 (13)
C12	0.0693 (17)	0.0440 (12)	0.0609 (15)	−0.0005 (12)	0.0261 (13)	0.0192 (11)
C13	0.0719 (17)	0.0372 (11)	0.0455 (12)	0.0144 (11)	0.0191 (12)	0.0176 (10)
C14	0.0481 (12)	0.0381 (11)	0.0405 (11)	0.0124 (9)	0.0105 (9)	0.0117 (9)
C15	0.0519 (13)	0.0318 (10)	0.0481 (12)	0.0084 (9)	0.0195 (10)	0.0141 (9)
C16	0.0623 (14)	0.0350 (11)	0.0536 (13)	0.0080 (10)	0.0231 (11)	0.0160 (10)
C17	0.092 (2)	0.0373 (12)	0.0723 (17)	0.0202 (13)	0.0353 (15)	0.0262 (12)
C18	0.090 (2)	0.0608 (16)	0.0817 (19)	0.0423 (16)	0.0340 (16)	0.0373 (14)
C19	0.0578 (16)	0.0714 (17)	0.0844 (19)	0.0266 (14)	0.0247 (14)	0.0345 (15)
C20	0.0545 (15)	0.0424 (12)	0.0703 (16)	0.0131 (11)	0.0219 (12)	0.0231 (11)
C21	0.088 (9)	0.066 (9)	0.071 (9)	0.014 (8)	−0.001 (6)	0.048 (8)
C22	0.109 (12)	0.121 (12)	0.091 (10)	−0.032 (8)	−0.022 (8)	0.006 (8)
C23	0.157 (13)	0.077 (7)	0.044 (7)	0.004 (9)	−0.017 (9)	−0.004 (6)
C24	0.107 (6)	0.190 (8)	0.238 (11)	0.020 (6)	−0.016 (6)	0.142 (8)
C25	0.107 (6)	0.190 (8)	0.238 (11)	0.020 (6)	−0.016 (6)	0.142 (8)
C21A	0.088 (10)	0.059 (8)	0.044 (6)	−0.039 (7)	−0.007 (6)	0.001 (5)
C22A	0.150 (12)	0.108 (7)	0.114 (7)	−0.078 (8)	−0.109 (8)	0.088 (6)
C23A	0.219 (19)	0.100 (14)	0.074 (9)	−0.004 (12)	0.078 (11)	−0.003 (8)
C24A	0.073 (7)	0.076 (8)	0.111 (11)	−0.020 (5)	0.004 (6)	0.069 (8)
C25A	0.135 (9)	0.100 (6)	0.122 (8)	0.002 (6)	0.007 (7)	0.015 (6)
Cl2	0.0669 (4)	0.0464 (3)	0.1071 (6)	−0.0064 (3)	0.0240 (4)	0.0251 (3)
Cl1	0.0531 (4)	0.0934 (5)	0.0785 (5)	0.0225 (4)	0.0065 (3)	0.0456 (4)
N1	0.0528 (11)	0.0326 (9)	0.0536 (11)	0.0125 (8)	0.0256 (9)	0.0176 (8)
O1	0.0477 (10)	0.0753 (12)	0.1089 (15)	0.0197 (9)	0.0349 (10)	0.0412 (11)

Geometric parameters (Å, º) top

C1—N1	1.461 (3)	C17—C18	1.364 (4)
C1—C9	1.516 (3)	C17—H17	0.9300
C1—C2	1.554 (3)	C18—C19	1.378 (4)
C1—H1	0.9800	C18—H18	0.9300
C2—C8	1.505 (3)	C19—C20	1.380 (3)
C2—C3	1.536 (3)	C19—H19	0.9300
C2—H2	0.9800	C20—H20	0.9300
C3—C4	1.534 (3)	C21—C23	1.46 (3)
C3—H3A	0.9700	C21—C22	1.51 (3)
C3—H3B	0.9700	C21—C24	1.56 (3)
C4—C21	1.454 (19)	C22—H22A	0.9600
C4—C5	1.535 (3)	C22—H22B	0.9600
C4—C21A	1.636 (19)	C22—H22C	0.9600
C4—H4	0.9800	C23—H23A	0.9600
C5—C6	1.539 (3)	C23—H23B	0.9600
C5—H5A	0.9700	C23—H23C	0.9600
C5—H5B	0.9700	C24—C25	1.309 (18)
C6—C8	1.497 (3)	C24—H24A	0.9700
C6—C7	1.552 (3)	C24—H24B	0.9700
C6—H6	0.9800	C25—H25A	0.9600
C7—N1	1.467 (3)	C25—H25B	0.9600
C7—C15	1.511 (3)	C25—H25C	0.9600
C7—H7	0.9800	C21A—C24A	1.55 (3)
C8—O1	1.209 (3)	C21A—C22A	1.61 (3)
C9—C10	1.388 (3)	C21A—C23A	1.64 (4)
C9—C14	1.395 (3)	C22A—H22D	0.9600
C10—C11	1.381 (3)	C22A—H22E	0.9600
C10—H10	0.9300	C22A—H22F	0.9600
C11—C12	1.370 (4)	C23A—H23D	0.9600
C11—H11	0.9300	C23A—H23E	0.9600
C12—C13	1.371 (3)	C23A—H23F	0.9600
C12—H12	0.9300	C24A—C25A	1.27 (3)
C13—C14	1.384 (3)	C24A—H24C	0.9700
C13—H13	0.9300	C24A—H24D	0.9700
C14—Cl1	1.742 (2)	C25A—H25D	0.9600
C15—C20	1.384 (3)	C25A—H25E	0.9600
C15—C16	1.394 (3)	C25A—H25F	0.9600
C16—C17	1.374 (3)	N1—H1N	0.89 (2)
C16—Cl2	1.745 (2)

N1—C1—C9	110.16 (16)	C16—C17—H17	120.1
N1—C1—C2	109.81 (17)	C17—C18—C19	119.6 (2)
C9—C1—C2	111.03 (16)	C17—C18—H18	120.2
N1—C1—H1	108.6	C19—C18—H18	120.2
C9—C1—H1	108.6	C18—C19—C20	120.3 (3)
C2—C1—H1	108.6	C18—C19—H19	119.9
C8—C2—C3	108.14 (18)	C20—C19—H19	119.9
C8—C2—C1	107.25 (16)	C19—C20—C15	121.5 (2)
C3—C2—C1	115.74 (18)	C19—C20—H20	119.3
C8—C2—H2	108.5	C15—C20—H20	119.3
C3—C2—H2	108.5	C4—C21—C23	117.1 (18)
C1—C2—H2	108.5	C4—C21—C22	113.0 (14)
C4—C3—C2	115.32 (17)	C23—C21—C22	100.3 (18)
C4—C3—H3A	108.4	C4—C21—C24	111.8 (14)
C2—C3—H3A	108.4	C23—C21—C24	102.4 (18)
C4—C3—H3B	108.4	C22—C21—C24	111 (2)
C2—C3—H3B	108.4	C21—C22—H22A	109.4
H3A—C3—H3B	107.5	C21—C22—H22B	109.5
C21—C4—C3	113.1 (6)	H22A—C22—H22B	109.5
C21—C4—C5	112.9 (9)	C21—C22—H22C	109.5
C3—C4—C5	110.78 (19)	H22A—C22—H22C	109.5
C3—C4—C21A	114.5 (8)	H22B—C22—H22C	109.5
C5—C4—C21A	112.2 (9)	C21—C23—H23A	109.5
C21—C4—H4	106.5	C21—C23—H23B	109.5
C3—C4—H4	106.5	H23A—C23—H23B	109.5
C5—C4—H4	106.5	C21—C23—H23C	109.4
C4—C5—C6	115.05 (18)	H23A—C23—H23C	109.5
C4—C5—H5A	108.5	H23B—C23—H23C	109.5
C6—C5—H5A	108.5	C25—C24—C21	132.5 (17)
C4—C5—H5B	108.5	C25—C24—H24A	103.9
C6—C5—H5B	108.5	C21—C24—H24A	103.9
H5A—C5—H5B	107.5	C25—C24—H24B	104.4
C8—C6—C5	108.55 (17)	C21—C24—H24B	104.3
C8—C6—C7	107.09 (18)	H24A—C24—H24B	105.5
C5—C6—C7	115.73 (18)	C24—C25—H25A	109.3
C8—C6—H6	108.4	C24—C25—H25B	109.3
C5—C6—H6	108.4	H25A—C25—H25B	109.5
C7—C6—H6	108.4	C24—C25—H25C	109.8
N1—C7—C15	109.85 (17)	H25A—C25—H25C	109.5
N1—C7—C6	109.86 (16)	H25B—C25—H25C	109.5
C15—C7—C6	112.34 (18)	C24A—C21A—C22A	106 (2)
N1—C7—H7	108.2	C24A—C21A—C4	107.5 (15)
C15—C7—H7	108.2	C22A—C21A—C4	105.6 (13)
C6—C7—H7	108.2	C24A—C21A—C23A	108.6 (19)
O1—C8—C6	124.7 (2)	C22A—C21A—C23A	120.0 (18)
O1—C8—C2	124.2 (2)	C4—C21A—C23A	108.1 (18)
C6—C8—C2	111.14 (18)	C21A—C22A—H22D	109.6
C10—C9—C14	116.29 (18)	C21A—C22A—H22E	109.3
C10—C9—C1	121.34 (18)	H22D—C22A—H22E	109.5
C14—C9—C1	122.33 (18)	C21A—C22A—H22F	109.5
C11—C10—C9	121.6 (2)	H22D—C22A—H22F	109.5
C11—C10—H10	119.2	H22E—C22A—H22F	109.5
C9—C10—H10	119.2	C21A—C23A—H23D	109.5
C12—C11—C10	120.7 (2)	C21A—C23A—H23E	109.5
C12—C11—H11	119.7	H23D—C23A—H23E	109.5
C10—C11—H11	119.7	C21A—C23A—H23F	109.4
C11—C12—C13	119.5 (2)	H23D—C23A—H23F	109.5
C11—C12—H12	120.2	H23E—C23A—H23F	109.5
C13—C12—H12	120.2	C25A—C24A—C21A	121.8 (19)
C12—C13—C14	119.6 (2)	C25A—C24A—H24C	106.9
C12—C13—H13	120.2	C21A—C24A—H24C	106.9
C14—C13—H13	120.2	C25A—C24A—H24D	106.9
C13—C14—C9	122.3 (2)	C21A—C24A—H24D	106.9
C13—C14—Cl1	117.25 (17)	H24C—C24A—H24D	106.7
C9—C14—Cl1	120.43 (16)	C24A—C25A—H25D	109.5
C20—C15—C16	116.5 (2)	C24A—C25A—H25E	109.5
C20—C15—C7	121.22 (18)	H25D—C25A—H25E	109.5
C16—C15—C7	122.3 (2)	C24A—C25A—H25F	109.5
C17—C16—C15	122.3 (2)	H25D—C25A—H25F	109.5
C17—C16—Cl2	117.35 (18)	H25E—C25A—H25F	109.5
C15—C16—Cl2	120.29 (18)	C1—N1—C7	114.20 (16)
C18—C17—C16	119.8 (2)	C1—N1—H1N	108.7 (16)
C18—C17—H17	120.1	C7—N1—H1N	108.5 (15)

N1—C1—C2—C8	−56.9 (2)	C6—C7—C15—C20	−95.7 (2)
C9—C1—C2—C8	−179.01 (17)	N1—C7—C15—C16	−151.6 (2)
N1—C1—C2—C3	63.8 (2)	C6—C7—C15—C16	85.8 (2)
C9—C1—C2—C3	−58.2 (2)	C20—C15—C16—C17	−1.3 (3)
C8—C2—C3—C4	53.9 (2)	C7—C15—C16—C17	177.4 (2)
C1—C2—C3—C4	−66.4 (2)	C20—C15—C16—Cl2	−179.97 (17)
C2—C3—C4—C21	−172.6 (12)	C7—C15—C16—Cl2	−1.3 (3)
C2—C3—C4—C5	−44.7 (2)	C15—C16—C17—C18	0.8 (4)
C2—C3—C4—C21A	−172.9 (11)	Cl2—C16—C17—C18	179.6 (2)
C21—C4—C5—C6	172.3 (9)	C16—C17—C18—C19	0.4 (4)
C3—C4—C5—C6	44.4 (2)	C17—C18—C19—C20	−1.1 (4)
C21A—C4—C5—C6	173.7 (10)	C18—C19—C20—C15	0.6 (4)
C4—C5—C6—C8	−53.6 (2)	C16—C15—C20—C19	0.6 (3)
C4—C5—C6—C7	66.8 (2)	C7—C15—C20—C19	−178.1 (2)
C8—C6—C7—N1	57.4 (2)	C3—C4—C21—C23	70.0 (17)
C5—C6—C7—N1	−63.8 (2)	C5—C4—C21—C23	−56.8 (16)
C8—C6—C7—C15	−179.99 (17)	C21A—C4—C21—C23	−120 (81)
C5—C6—C7—C15	58.8 (2)	C3—C4—C21—C22	−46 (2)
C5—C6—C8—O1	−116.6 (3)	C5—C4—C21—C22	−172.5 (16)
C7—C6—C8—O1	117.7 (2)	C21A—C4—C21—C22	125 (82)
C5—C6—C8—C2	63.0 (2)	C3—C4—C21—C24	−172.4 (14)
C7—C6—C8—C2	−62.6 (2)	C5—C4—C21—C24	61 (2)
C3—C2—C8—O1	116.6 (3)	C21A—C4—C21—C24	−2 (79)
C1—C2—C8—O1	−117.9 (2)	C4—C21—C24—C25	148 (3)
C3—C2—C8—C6	−63.0 (2)	C23—C21—C24—C25	−86 (3)
C1—C2—C8—C6	62.4 (2)	C22—C21—C24—C25	20 (4)
N1—C1—C9—C10	−23.9 (3)	C21—C4—C21A—C24A	−63 (79)
C2—C1—C9—C10	97.9 (2)	C3—C4—C21A—C24A	−53 (2)
N1—C1—C9—C14	158.49 (18)	C5—C4—C21A—C24A	179.7 (14)
C2—C1—C9—C14	−79.6 (2)	C21—C4—C21A—C22A	−176 (100)
C14—C9—C10—C11	1.2 (3)	C3—C4—C21A—C22A	−166.3 (11)
C1—C9—C10—C11	−176.5 (2)	C5—C4—C21A—C22A	66.3 (17)
C9—C10—C11—C12	−0.6 (4)	C21—C4—C21A—C23A	54 (80)
C10—C11—C12—C13	−0.4 (4)	C3—C4—C21A—C23A	64.1 (18)
C11—C12—C13—C14	0.7 (3)	C5—C4—C21A—C23A	−63.3 (17)
C12—C13—C14—C9	−0.1 (3)	C22A—C21A—C24A—C25A	49 (2)
C12—C13—C14—Cl1	179.93 (17)	C4—C21A—C24A—C25A	−64 (2)
C10—C9—C14—C13	−0.8 (3)	C23A—C21A—C24A—C25A	179.7 (17)
C1—C9—C14—C13	176.83 (18)	C9—C1—N1—C7	179.34 (17)
C10—C9—C14—Cl1	179.14 (15)	C2—C1—N1—C7	56.8 (2)
C1—C9—C14—Cl1	−3.2 (3)	C15—C7—N1—C1	178.90 (17)
N1—C7—C15—C20	27.0 (3)	C6—C7—N1—C1	−57.0 (2)

Experimental details

Crystal data
Chemical formula	C₂₅H₂₉Cl₂NO
M_r	430.39
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.6006 (3), 10.6240 (5), 15.1124 (7)
α, β, γ (°)	106.116 (2), 99.996 (2), 98.266 (2)
V (Å³)	1130.54 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.30
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2004)
T_min, T_max	0.928, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	13160, 3789, 2944
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.119, 1.02
No. of reflections	3789
No. of parameters	313
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.27

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012).

Acknowledgements

This research was supported by Inje University Research Grant 2014.

References

Bruker (2004). APEX2, XPREP, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Padegimas, S. J. & Kovacic, P. (1972). J. Org. Chem. 37, 2672–2676. CrossRef CAS Web of Science Google Scholar
Park, D. H., Jeong, Y. T. & Parthiban, P. (2011). J. Mol. Struct. 1005, 31–44. Web of Science CrossRef CAS Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2946. CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Ramkumar, V. & Parthiban, P. (2012c). Acta Cryst. E68, o1481. CSD CrossRef IUCr Journals Google Scholar
Park, D. H., Venkatesan, J., Kim, S. K. & Parthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004–6009. Web of Science CSD CrossRef CAS PubMed Google Scholar
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2010). Acta Cryst. E66, o194–o195. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. 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.