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

Parthiban, P.; Ramkumar, V.; Kim, M.S.; Kabilan, S.; Jeong, Y.T.

doi:10.1107/S160053680900590X

organic compounds

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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o609

doi:10.1107/S160053680900590X

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

P. Parthiban,^a V. Ramkumar,^b Min Sung Kim,^a S. Kabilan ^c and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, ^bDepartment of Chemistry, IIT Madras, Chennai, TamilNadu, India, and ^cDepartment of Chemistry, Annamalai University, Annamalai Nagar, TamilNadu, India
^*Correspondence e-mail: ytjeong@pknu.ac.kr

(Received 4 February 2009; accepted 19 February 2009; online 25 February 2009)

In the molecular structure of the title compound, C₂₀H₁₉Cl₂NO, the molecule exists in a twin-chair conformation with equatorial dispositions of the 4-chlorophenyl groups on both sides of the secondary amino group; the dihedral angle between the aromatic ring planes is 31.33 (3)°. The crystal structure is stabilized by N—H⋯O interactions, leading to chains of molecules.

Related literature

For the biological activity of diterpenoid/norditerpenoid alkaloids, see: Hardick et al. (1996 ); Jeyaraman et al. (1981 ). For similiar structures, see: Parthiban et al. (2008a ,b ,c ,d ,e ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₁₉Cl₂NO
M_r = 360.26
Monoclinic, P 2₁ /n
a = 16.2589 (4) Å
b = 6.8983 (2) Å
c = 18.1291 (5) Å
β = 116.149 (1)°
V = 1825.23 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.36 mm⁻¹
T = 298 K
0.42 × 0.38 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.863, T_max = 0.915
15050 measured reflections
4997 independent reflections
3241 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.135
S = 1.02
4997 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.85 (2)	2.31 (2)	3.1202 (18)	160.2 (18)
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT-Plus (Bruker, 2004); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900590X/bq2124sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900590X/bq2124Isup2.hkl

checkCIF report

Comment top

The widespread diterpenoid/norditerpenoid alkaloids posses the 3-azabicyclo [3.3.1]nonane pharmacophore, and as a consequence, the above alkaloids having broad spectrum of biological activities (Jeyaraman et al., 1981; Hardick et al., 1996). Hence, the synthesis and stereochemistry of 3-azabicyclononan-9-ones are more important in recent days (Parthiban et al., 2008a,b,c,d,e). A study of torsion angles, asymmetry parameters and least-squares plane calculation shows that the piperidine ring adopts near ideal chair conformation with the deviation of ring atoms N1 and C8 from the C1/C2/C6/C7 plane by -0.642 (3)Å and 0.712 (3)Å, respectively, Q_T=0.607 (2)Å, q(2)=0.044 (2)Å and q(3)=-0.606 (2)Å, θ=175.8 (2)°. whereas the cyclohexane ring deviate from the ideal chair conformation; the cyclohexane atoms C4 and C8 deviate from the C2/C3/C5/C6 plane by -0.557 (2)Å and 0.710 (3)Å, respectively, Q_T=0.560 (2) Å, q(2)=0.117 (2)Å and, q(3)=-0.548 (2)Å, θ=167.9 (2)°. (Cremer & Pople, 1975). Hence, the title compound C₂₀H₁₉Cl₂NO, exists in double chair conformation with equatorial dispositions of the para chlorophenyl groups with the torsion angles of C8—C2—C1—C9 and C8—C6—C7—C15 are 177.88 (4)° and -179.01 (4)°, respectively. The aryl groups are oriented at an angle of 31.33 (3)° to each other.

Related literature top

For the biological activity of diterpenoid/norditerpenoid alkaloids, see: Hardick et al. (1996); Jeyaraman et al. (1981). For similiar structures, see: Parthiban et al. (2008a,b,c,d,e). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

In a warm solution of ammonium acetate (0.075 mol) in 50 ml of absolute ethanol, a mixture of cyclohexanone (0.05 mol) and para chlorobenzaldehyde (0.1 mol) was added and gently warmed with stirring on a hot plate till the yellow color was formed during the mixing of the reactants and cooled to room temperature. Then 50 ml of ether was added and allowed to stir over night at room temperature. Thus the obtained crude azabicyclic ketone was separated by filtration and washed with 1:5 ethanol-ether mixture till the solid became colorless. Recrystallization of the compound from ethanol gave X-ray diffraction quality crystals of 2,4-bis(4-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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).

Figures top

	Fig. 1. ORTEP of the molecule with atoms represented as 30% probability ellipsoids.
	Fig. 2. Packing of molecules via N-H..O bond.

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

Crystal data top

C₂₀H₁₉Cl₂NO	F(000) = 752
M_r = 360.26	D_x = 1.311 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4308 reflections
a = 16.2589 (4) Å	θ = 2.8–26.3°
b = 6.8983 (2) Å	µ = 0.36 mm⁻¹
c = 18.1291 (5) Å	T = 298 K
β = 116.149 (1)°	Rectangular, colourless
V = 1825.23 (9) Å³	0.42 × 0.38 × 0.25 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4997 independent reflections
Radiation source: fine-focus sealed tube	3241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 29.8°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −21→20
T_min = 0.863, T_max = 0.915	k = −9→9
15050 measured reflections	l = −15→25

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0602P)² + 0.4485P] where P = (F_o² + 2F_c²)/3
4997 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.38 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₂₀H₁₉Cl₂NO	V = 1825.23 (9) Å³
M_r = 360.26	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 16.2589 (4) Å	µ = 0.36 mm⁻¹
b = 6.8983 (2) Å	T = 298 K
c = 18.1291 (5) Å	0.42 × 0.38 × 0.25 mm
β = 116.149 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4997 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	3241 reflections with I > 2σ(I)
T_min = 0.863, T_max = 0.915	R_int = 0.021
15050 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.38 e Å⁻³
4997 reflections	Δρ_min = −0.42 e Å⁻³
221 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.

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.

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

	x	y	z	U_iso*/U_eq
C1	0.33305 (11)	0.1260 (2)	0.01759 (10)	0.0384 (3)
H1	0.3907	0.1019	0.0665	0.046*
C2	0.29289 (11)	−0.0738 (2)	−0.02171 (10)	0.0410 (4)
H2	0.3380	−0.1414	−0.0345	0.049*
C3	0.20110 (12)	−0.0678 (3)	−0.09929 (11)	0.0533 (4)
H3A	0.2079	0.0135	−0.1399	0.064*
H3B	0.1864	−0.1977	−0.1219	0.064*
C4	0.12129 (12)	0.0082 (3)	−0.08496 (12)	0.0581 (5)
H4A	0.1268	0.1478	−0.0779	0.070*
H4B	0.0643	−0.0190	−0.1330	0.070*
C5	0.11811 (12)	−0.0827 (3)	−0.00979 (12)	0.0534 (5)
H5A	0.0944	−0.2136	−0.0235	0.064*
H5B	0.0756	−0.0096	0.0037	0.064*
C6	0.21147 (11)	−0.0905 (2)	0.06658 (11)	0.0418 (4)
H6	0.2052	−0.1688	0.1090	0.050*
C7	0.25223 (11)	0.1109 (2)	0.10384 (10)	0.0375 (3)
H7	0.3106	0.0893	0.1524	0.045*
C8	0.27891 (11)	−0.1870 (2)	0.04285 (10)	0.0390 (4)
C9	0.35398 (11)	0.2533 (2)	−0.03978 (10)	0.0414 (4)
C10	0.29057 (13)	0.3777 (3)	−0.09592 (12)	0.0544 (5)
H10	0.2316	0.3836	−0.1000	0.065*
C11	0.31400 (15)	0.4943 (3)	−0.14645 (12)	0.0615 (5)
H11	0.2710	0.5776	−0.1841	0.074*
C12	0.40091 (16)	0.4852 (3)	−0.14022 (12)	0.0584 (5)
C13	0.46439 (15)	0.3618 (3)	−0.08633 (14)	0.0654 (6)
H13	0.5228	0.3545	−0.0835	0.078*
C14	0.44093 (13)	0.2474 (3)	−0.03588 (13)	0.0555 (5)
H14	0.4845	0.1646	0.0015	0.067*
C15	0.18866 (11)	0.2164 (2)	0.13081 (10)	0.0385 (3)
C16	0.17785 (12)	0.1464 (3)	0.19803 (11)	0.0473 (4)
H16	0.2125	0.0407	0.2271	0.057*
C17	0.11692 (13)	0.2301 (3)	0.22247 (11)	0.0528 (4)
H17	0.1097	0.1804	0.2670	0.063*
C18	0.06701 (12)	0.3877 (3)	0.18023 (12)	0.0509 (4)
C19	0.07748 (13)	0.4646 (3)	0.11480 (12)	0.0540 (5)
H19	0.0446	0.5740	0.0877	0.065*
C20	0.13769 (12)	0.3765 (2)	0.08997 (11)	0.0471 (4)
H20	0.1440	0.4259	0.0450	0.057*
Cl1	−0.01108 (4)	0.49239 (10)	0.21027 (4)	0.0838 (2)
Cl2	0.43337 (5)	0.64178 (11)	−0.19813 (4)	0.0956 (3)
N1	0.27045 (9)	0.2229 (2)	0.04419 (9)	0.0401 (3)
O1	0.31840 (9)	−0.33704 (16)	0.07301 (8)	0.0515 (3)
H1A	0.2917 (13)	0.334 (3)	0.0645 (12)	0.058 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0379 (8)	0.0331 (8)	0.0479 (9)	−0.0024 (6)	0.0223 (7)	0.0015 (7)
C2	0.0440 (9)	0.0329 (8)	0.0532 (9)	−0.0007 (7)	0.0278 (8)	−0.0020 (7)
C3	0.0591 (11)	0.0489 (10)	0.0498 (10)	−0.0103 (9)	0.0221 (9)	−0.0051 (8)
C4	0.0413 (10)	0.0552 (12)	0.0634 (12)	−0.0046 (8)	0.0100 (9)	−0.0021 (10)
C5	0.0407 (9)	0.0473 (10)	0.0750 (13)	−0.0100 (8)	0.0279 (9)	−0.0112 (9)
C6	0.0462 (9)	0.0304 (8)	0.0578 (10)	−0.0030 (7)	0.0312 (8)	0.0018 (7)
C7	0.0387 (8)	0.0317 (7)	0.0458 (9)	0.0003 (6)	0.0218 (7)	0.0016 (7)
C8	0.0401 (8)	0.0273 (7)	0.0514 (9)	−0.0059 (6)	0.0219 (7)	−0.0053 (7)
C9	0.0470 (9)	0.0327 (8)	0.0530 (9)	−0.0049 (7)	0.0298 (8)	−0.0023 (7)
C10	0.0526 (11)	0.0557 (11)	0.0635 (11)	0.0042 (9)	0.0334 (9)	0.0110 (9)
C11	0.0770 (14)	0.0560 (12)	0.0556 (11)	0.0002 (10)	0.0331 (11)	0.0112 (9)
C12	0.0821 (14)	0.0544 (11)	0.0527 (10)	−0.0244 (10)	0.0424 (10)	−0.0081 (9)
C13	0.0637 (13)	0.0668 (13)	0.0862 (15)	−0.0121 (11)	0.0517 (12)	0.0008 (12)
C14	0.0514 (11)	0.0483 (10)	0.0781 (13)	−0.0017 (8)	0.0387 (10)	0.0053 (9)
C15	0.0397 (8)	0.0334 (8)	0.0445 (8)	−0.0023 (6)	0.0205 (7)	−0.0035 (7)
C16	0.0531 (10)	0.0452 (10)	0.0471 (9)	0.0052 (8)	0.0254 (8)	0.0035 (8)
C17	0.0584 (11)	0.0601 (12)	0.0475 (10)	−0.0022 (9)	0.0305 (9)	−0.0062 (9)
C18	0.0442 (10)	0.0534 (11)	0.0576 (11)	−0.0012 (8)	0.0249 (9)	−0.0186 (9)
C19	0.0515 (11)	0.0435 (10)	0.0654 (12)	0.0096 (8)	0.0243 (9)	−0.0027 (9)
C20	0.0534 (10)	0.0394 (9)	0.0528 (10)	0.0025 (8)	0.0274 (8)	0.0022 (8)
Cl1	0.0721 (4)	0.0962 (5)	0.0986 (5)	0.0135 (3)	0.0519 (3)	−0.0262 (4)
Cl2	0.1246 (6)	0.1079 (5)	0.0667 (4)	−0.0502 (4)	0.0535 (4)	0.0061 (3)
N1	0.0490 (8)	0.0274 (6)	0.0524 (8)	−0.0046 (6)	0.0302 (7)	−0.0020 (6)
O1	0.0613 (8)	0.0313 (6)	0.0686 (8)	0.0042 (5)	0.0347 (7)	0.0037 (6)

Geometric parameters (Å, º) top

C1—N1	1.466 (2)	C9—C10	1.382 (3)
C1—C9	1.511 (2)	C9—C14	1.385 (2)
C1—C2	1.557 (2)	C10—C11	1.393 (3)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.505 (2)	C11—C12	1.368 (3)
C2—C3	1.535 (2)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.363 (3)
C3—C4	1.524 (3)	C12—Cl2	1.7422 (18)
C3—H3A	0.9700	C13—C14	1.383 (3)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.522 (3)	C14—H14	0.9300
C4—H4A	0.9700	C15—C20	1.383 (2)
C4—H4B	0.9700	C15—C16	1.392 (2)
C5—C6	1.540 (3)	C16—C17	1.378 (2)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—C18	1.371 (3)
C6—C8	1.499 (2)	C17—H17	0.9300
C6—C7	1.559 (2)	C18—C19	1.377 (3)
C6—H6	0.9800	C18—Cl1	1.7433 (17)
C7—N1	1.462 (2)	C19—C20	1.385 (2)
C7—C15	1.511 (2)	C19—H19	0.9300
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.2137 (19)	N1—H1A	0.85 (2)

N1—C1—C9	111.16 (13)	O1—C8—C6	123.91 (15)
N1—C1—C2	110.05 (12)	O1—C8—C2	124.16 (15)
C9—C1—C2	112.08 (13)	C6—C8—C2	111.92 (13)
N1—C1—H1	107.8	C10—C9—C14	118.01 (16)
C9—C1—H1	107.8	C10—C9—C1	123.14 (15)
C2—C1—H1	107.8	C14—C9—C1	118.85 (16)
C8—C2—C3	107.89 (13)	C9—C10—C11	120.76 (18)
C8—C2—C1	106.25 (13)	C9—C10—H10	119.6
C3—C2—C1	115.97 (14)	C11—C10—H10	119.6
C8—C2—H2	108.8	C12—C11—C10	119.42 (19)
C3—C2—H2	108.8	C12—C11—H11	120.3
C1—C2—H2	108.8	C10—C11—H11	120.3
C4—C3—C2	114.21 (15)	C13—C12—C11	121.07 (17)
C4—C3—H3A	108.7	C13—C12—Cl2	118.99 (16)
C2—C3—H3A	108.7	C11—C12—Cl2	119.86 (18)
C4—C3—H3B	108.7	C12—C13—C14	119.24 (19)
C2—C3—H3B	108.7	C12—C13—H13	120.4
H3A—C3—H3B	107.6	C14—C13—H13	120.4
C5—C4—C3	112.21 (16)	C13—C14—C9	121.49 (19)
C5—C4—H4A	109.2	C13—C14—H14	119.3
C3—C4—H4A	109.2	C9—C14—H14	119.3
C5—C4—H4B	109.2	C20—C15—C16	117.94 (15)
C3—C4—H4B	109.2	C20—C15—C7	123.06 (14)
H4A—C4—H4B	107.9	C16—C15—C7	118.96 (14)
C4—C5—C6	114.24 (14)	C17—C16—C15	121.48 (17)
C4—C5—H5A	108.7	C17—C16—H16	119.3
C6—C5—H5A	108.7	C15—C16—H16	119.3
C4—C5—H5B	108.7	C18—C17—C16	119.03 (17)
C6—C5—H5B	108.7	C18—C17—H17	120.5
H5A—C5—H5B	107.6	C16—C17—H17	120.5
C8—C6—C5	108.27 (14)	C17—C18—C19	121.29 (16)
C8—C6—C7	107.15 (12)	C17—C18—Cl1	119.16 (15)
C5—C6—C7	114.88 (14)	C19—C18—Cl1	119.55 (15)
C8—C6—H6	108.8	C18—C19—C20	118.97 (17)
C5—C6—H6	108.8	C18—C19—H19	120.5
C7—C6—H6	108.8	C20—C19—H19	120.5
N1—C7—C15	112.03 (12)	C15—C20—C19	121.25 (17)
N1—C7—C6	109.68 (13)	C15—C20—H20	119.4
C15—C7—C6	110.42 (12)	C19—C20—H20	119.4
N1—C7—H7	108.2	C7—N1—C1	113.48 (12)
C15—C7—H7	108.2	C7—N1—H1A	109.2 (14)
C6—C7—H7	108.2	C1—N1—H1A	110.1 (13)

N1—C1—C2—C8	−57.87 (16)	C1—C9—C10—C11	178.93 (17)
C9—C1—C2—C8	177.89 (13)	C9—C10—C11—C12	0.0 (3)
N1—C1—C2—C3	61.99 (18)	C10—C11—C12—C13	1.1 (3)
C9—C1—C2—C3	−62.25 (18)	C10—C11—C12—Cl2	−175.72 (16)
C8—C2—C3—C4	53.9 (2)	C11—C12—C13—C14	−1.5 (3)
C1—C2—C3—C4	−65.1 (2)	Cl2—C12—C13—C14	175.27 (16)
C2—C3—C4—C5	−46.3 (2)	C12—C13—C14—C9	1.0 (3)
C3—C4—C5—C6	45.7 (2)	C10—C9—C14—C13	0.0 (3)
C4—C5—C6—C8	−53.0 (2)	C1—C9—C14—C13	−179.45 (18)
C4—C5—C6—C7	66.6 (2)	N1—C7—C15—C20	14.1 (2)
C8—C6—C7—N1	57.05 (17)	C6—C7—C15—C20	−108.49 (17)
C5—C6—C7—N1	−63.26 (17)	N1—C7—C15—C16	−168.34 (15)
C8—C6—C7—C15	−179.02 (13)	C6—C7—C15—C16	69.09 (19)
C5—C6—C7—C15	60.67 (18)	C20—C15—C16—C17	1.5 (3)
C5—C6—C8—O1	−118.50 (18)	C7—C15—C16—C17	−176.24 (16)
C7—C6—C8—O1	117.07 (17)	C15—C16—C17—C18	−1.0 (3)
C5—C6—C8—C2	62.45 (17)	C16—C17—C18—C19	−0.8 (3)
C7—C6—C8—C2	−61.98 (17)	C16—C17—C18—Cl1	179.30 (14)
C3—C2—C8—O1	118.08 (18)	C17—C18—C19—C20	2.0 (3)
C1—C2—C8—O1	−116.94 (17)	Cl1—C18—C19—C20	−178.05 (14)
C3—C2—C8—C6	−62.87 (17)	C16—C15—C20—C19	−0.2 (3)
C1—C2—C8—C6	62.11 (17)	C7—C15—C20—C19	177.44 (16)
N1—C1—C9—C10	−35.0 (2)	C18—C19—C20—C15	−1.5 (3)
C2—C1—C9—C10	88.57 (19)	C15—C7—N1—C1	179.14 (13)
N1—C1—C9—C14	144.36 (16)	C6—C7—N1—C1	−57.87 (17)
C2—C1—C9—C14	−92.02 (19)	C9—C1—N1—C7	−176.47 (13)
C14—C9—C10—C11	−0.5 (3)	C2—C1—N1—C7	58.76 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.85 (2)	2.31 (2)	3.1202 (18)	160.2 (18)

Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉Cl₂NO
M_r	360.26
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	16.2589 (4), 6.8983 (2), 18.1291 (5)
β (°)	116.149 (1)
V (Å³)	1825.23 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.36
Crystal size (mm)	0.42 × 0.38 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.863, 0.915
No. of measured, independent and observed [I > 2σ(I)] reflections	15050, 4997, 3241
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.699

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.135, 1.02
No. of reflections	4997
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.38, −0.42

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.85 (2)	2.31 (2)	3.1202 (18)	160.2 (18)

Symmetry code: (i) x, y+1, z.

Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hardick, D. J., Blagbrough, I. S., Cooper, G., Potter, B. V. L., Critchley, T. & Wonnacott, S. (1996). J. Med. Chem. 39, 4860–4866. CrossRef CAS PubMed Web of Science Google Scholar
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149–174. CrossRef CAS Web of Science Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Lim, K. T. & Jeong, Y. T. (2008a). Acta Cryst. E64, o1586. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Lim, K. T. & Jeong, Y. T. (2008b). Acta Cryst. E64, o2332. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2008c). Acta Cryst. E64, o2385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Ramkumar, V., Santan, H. D., Kim, J. T. & Jeong, Y. T. (2008d). Acta Cryst. E64, o1710. Web of Science CSD CrossRef IUCr Journals Google Scholar
Parthiban, P., Thirumurugan, K., Ramkumar, V., Pazhamalai, S. & Jeong, Y. T. (2008e). Acta Cryst. E64, o1708–o1709. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar