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

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

doi:10.1107/S160053680802268X

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1586

doi:10.1107/S160053680802268X

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

P. Parthiban,^a V. Ramkumar,^b Min Sung Kim,^a Kwon Taek Lim ^a and Yeon Tae Jeong ^a ^*

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

(Received 14 July 2008; accepted 19 July 2008; online 26 July 2008)

The molecular structure of the title compound, C₂₀H₁₉Cl₂NO, reveals chair conformations for both six-membered rings of the bicyclic system. Both 2-chlorophenyl groups adopt equatorial dispositions with the chloro substituents oriented towards the carbonyl group; the aryl groups are orientated at an angle of 28.64 (3)° with respect to each other.

Related literature

For related literature, see: Buxton et al. (1996 ); Jeyaraman et al. (1981 ); Zefirov et al. (1990 ); Vijayalakshmi et al. (2000 ); Web et al. (1967 ); Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₁₉Cl₂NO
M_r = 360.26
Triclinic, $[P \overline 1]$
a = 7.7070 (15) Å
b = 10.680 (2) Å
c = 11.000 (2) Å
α = 101.78 (3)°
β = 92.82 (3)°
γ = 98.13 (3)°
V = 874.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298 (2) K
0.32 × 0.25 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.889, T_max = 0.928
9470 measured reflections
2949 independent reflections
2478 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.309
S = 1.19
2949 reflections
221 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802268X/bx2162sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802268X/bx2162Isup2.hkl

checkCIF report

Comment top

Since the biological activities mainly depend on the stereochemistry (Jeyaraman & Avila, 1981; Buxton & Roberts, 1996) it is worthwhile to study the stereochemistry and conformation of the organic molecules. Generally, these classes of bicyclic system prefer chair-chair conformation (Zefirov & Palyulin, 1990; Vijayalakshmi et al., 2000) among the three possible chair-chair, chair-boat and boat-boat conformations. However, NMR studies of this compound shows ambiguity over the conformation, due to the presence of electron withdrawing chloro substituents on ortho position of the either phenyl rings. Hence, we have carried out this X-ray analysis to establish the three dimensional structure.

The title compound C₂₀H₁₉Cl₂NO, exists in chair-chair conformation with equatorial orientations of the ortho phenyl groups on both side of the secondary amino group with the torsion angles C8—C6—C7—C15 and C8—C2—C1—C9 are 178.41 (6) ° and 179.12 (6) ° respectively.

In both aryl groups, the chloro substituents point upwards i.e., towards the carbonyl group and the aryl groups are orientated at an angle of 28.64 (3) ° to each other. A study of torsion angles, asymmetry parameters and least-squares plane calculation shows that the piperidine ring adopts near ideal chair conformation with a deviation of the ring atoms N1 and C8 from the C1/C2/C6/C7 plane by -0.630 (3) Å and 0.708 (3)Å respectively, Q_T = 0.593 (8)Å (D.Cremer & Pople, (1975)) whereas the cyclohexane ring atoms C4 and C8 deviate from the C2/C3/C5/C6 plane by -0.530 (4) Å and 0.730 (3) Å respectively (Q_T = 0.565 (8) Å.). Thus, indicating a deviation from the ideal chair conformation of the cyclohexane part in the title compound (Web & Becker, 1967).

Related literature top

For related literature, see: Buxton et al. (1996); Jeyaraman et al. (1981); Zefirov et al. (1990); Vijayalakshmi et al. (2000); Web et al. (1967); Cremer & Pople (1975).

Experimental top

A mixture of cyclohexanone (0.05 mol) and ortho chlorobenzaldehyde (0.1 mol) was added to a warm solution of ammonium acetate (0.75 mol) in 50 ml of absolute ethanol. The mixture was gently warmed on a hot plate till the yellow color formed during the mixing of the reactants and allowed to stir till the formation of the product. At the end, the pale yellow color azabicyclic ketone was separated by filtration and washed with 1:5 ethanol-ether mixture till the solid become colourless. Recrystallization of the compound from isopropyl alcohol (IPA) gave colourless crystals of 2,4-bis(2-chlorophenyl)-3-azabicyclo[3.3.1]nonan-9-one.

¹H NMR (400 MHz, CDCl3, p.p.m.): 8.05 (dd, J = 8.0, 1.2 Hz), 7.39 (dt, J = 7.0, 1.6 Hz), 7.27 (dt, J = 7.6, 1.8 Hz), 4.85 (d, H-2a, H-4a, J = 2.4 Hz), 2.88 (m, H-7a), 2.77 (s, H-1, 5), 1.90 (d, H-8 e, J = 4.8 Hz), 1.87 (dd, H-6 e, J = 4.8, 1.6 Hz), 1.81–1.71 (m, H-8a, H-6a), 1.66 (bs, N—H), 1.41 (quintet, H-7 e).

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: APEX2 (Bruker–Nonius, 2004); data reduction: SAINT-Plus (Bruker–Nonius, 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 view of the title molecule with atoms represented as 30% probability ellipsoids.

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

Crystal data top

C₂₀H₁₉Cl₂NO	Z = 2
M_r = 360.26	F(000) = 376
Triclinic, P1	D_x = 1.368 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7070 (15) Å	Cell parameters from 5271 reflections
b = 10.680 (2) Å	θ = 2.4–28.3°
c = 11.000 (2) Å	µ = 0.38 mm⁻¹
α = 101.78 (3)°	T = 298 K
β = 92.82 (3)°	Rectangular, colourless
γ = 98.13 (3)°	0.32 × 0.25 × 0.20 mm
V = 874.6 (3) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 25.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→9
T_min = 0.889, T_max = 0.928	k = −12→12
9470 measured reflections	l = −12→13

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.309	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ²(F_o²) + (0.0815P)² + 8.5055P] where P = (F_o² + 2F_c²)/3
2949 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₀H₁₉Cl₂NO	γ = 98.13 (3)°
M_r = 360.26	V = 874.6 (3) Å³
Triclinic, P1	Z = 2
a = 7.7070 (15) Å	Mo Kα radiation
b = 10.680 (2) Å	µ = 0.38 mm⁻¹
c = 11.000 (2) Å	T = 298 K
α = 101.78 (3)°	0.32 × 0.25 × 0.20 mm
β = 92.82 (3)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2949 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	2478 reflections with I > 2σ(I)
T_min = 0.889, T_max = 0.928	R_int = 0.026
9470 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.309	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.70 e Å⁻³
2949 reflections	Δρ_min = −0.41 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	0.2417 (9)	0.0189 (6)	0.1674 (6)	0.0272 (15)
H1	0.3149	0.0273	0.0982	0.033*
C2	0.3606 (9)	0.0002 (7)	0.2788 (7)	0.0324 (16)
H2	0.4171	−0.0762	0.2512	0.039*
C3	0.2618 (10)	−0.0165 (8)	0.3956 (7)	0.0377 (18)
H3A	0.1619	−0.0848	0.3702	0.045*
H3B	0.3398	−0.0445	0.4531	0.045*
C4	0.1957 (11)	0.1052 (8)	0.4652 (7)	0.0425 (19)
H4A	0.1688	0.0940	0.5479	0.051*
H4B	0.0879	0.1153	0.4215	0.051*
C5	0.3321 (11)	0.2301 (8)	0.4770 (7)	0.0433 (19)
H5A	0.2734	0.3047	0.5019	0.052*
H5B	0.4222	0.2325	0.5425	0.052*
C6	0.4220 (9)	0.2412 (7)	0.3553 (7)	0.0339 (17)
H6	0.5171	0.3153	0.3738	0.041*
C7	0.2987 (9)	0.2553 (6)	0.2452 (7)	0.0291 (15)
H7	0.3703	0.2650	0.1756	0.035*
C8	0.5010 (9)	0.1176 (7)	0.3144 (7)	0.0329 (16)
C9	0.0965 (9)	−0.0967 (6)	0.1234 (6)	0.0256 (14)
C10	−0.0743 (10)	−0.0946 (8)	0.1630 (7)	0.0360 (17)
H10	−0.0997	−0.0198	0.2142	0.043*
C11	−0.2061 (10)	−0.2016 (8)	0.1276 (8)	0.0430 (19)
H11	−0.3183	−0.1971	0.1539	0.052*
C12	−0.1697 (11)	−0.3152 (8)	0.0528 (8)	0.045 (2)
H12	−0.2570	−0.3873	0.0312	0.054*
C13	−0.0067 (11)	−0.3211 (7)	0.0112 (7)	0.0391 (18)
H13	0.0162	−0.3960	−0.0413	0.047*
C14	0.1257 (9)	−0.2140 (7)	0.0478 (6)	0.0297 (15)
C15	0.2078 (9)	0.3750 (7)	0.2778 (7)	0.0292 (15)
C16	0.2911 (10)	0.4984 (7)	0.2705 (7)	0.0335 (16)
C17	0.2106 (12)	0.6063 (8)	0.2961 (8)	0.047 (2)
H17	0.2695	0.6865	0.2893	0.057*
C18	0.0388 (12)	0.5946 (8)	0.3328 (9)	0.049 (2)
H18	−0.0172	0.6670	0.3512	0.058*
C19	−0.0466 (11)	0.4748 (8)	0.3413 (8)	0.046 (2)
H19	−0.1608	0.4666	0.3656	0.055*
C20	0.0360 (10)	0.3662 (7)	0.3141 (7)	0.0347 (17)
H20	−0.0241	0.2861	0.3202	0.042*
Cl1	0.3337 (3)	−0.2278 (2)	−0.0080 (2)	0.0567 (7)
Cl2	0.5064 (3)	0.5208 (2)	0.2224 (2)	0.0501 (7)
N1	0.1657 (8)	0.1389 (5)	0.2038 (6)	0.0290 (13)
O1	0.6563 (7)	0.1143 (6)	0.3131 (6)	0.0523 (16)
H1A	0.096 (12)	0.146 (8)	0.149 (9)	0.05 (3)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.023 (3)	0.028 (3)	0.030 (4)	0.006 (3)	0.003 (3)	0.001 (3)
C2	0.027 (4)	0.031 (4)	0.038 (4)	0.008 (3)	−0.004 (3)	0.005 (3)
C3	0.036 (4)	0.041 (4)	0.039 (4)	0.005 (3)	−0.004 (3)	0.017 (3)
C4	0.045 (5)	0.053 (5)	0.032 (4)	0.010 (4)	0.008 (4)	0.011 (4)
C5	0.050 (5)	0.043 (5)	0.033 (4)	0.010 (4)	−0.004 (4)	0.001 (3)
C6	0.025 (4)	0.029 (4)	0.043 (4)	−0.002 (3)	−0.007 (3)	0.002 (3)
C7	0.025 (4)	0.028 (3)	0.035 (4)	0.004 (3)	0.004 (3)	0.008 (3)
C8	0.028 (4)	0.036 (4)	0.035 (4)	0.006 (3)	0.000 (3)	0.008 (3)
C9	0.024 (3)	0.030 (3)	0.023 (3)	0.004 (3)	0.001 (3)	0.006 (3)
C10	0.029 (4)	0.039 (4)	0.038 (4)	0.010 (3)	0.005 (3)	0.000 (3)
C11	0.027 (4)	0.056 (5)	0.045 (5)	0.000 (4)	0.005 (3)	0.013 (4)
C12	0.048 (5)	0.039 (4)	0.042 (5)	−0.011 (4)	−0.007 (4)	0.011 (4)
C13	0.057 (5)	0.027 (4)	0.030 (4)	0.003 (3)	−0.003 (4)	0.002 (3)
C14	0.030 (4)	0.034 (4)	0.026 (3)	0.011 (3)	0.002 (3)	0.004 (3)
C15	0.028 (4)	0.029 (4)	0.031 (4)	0.005 (3)	0.000 (3)	0.006 (3)
C16	0.032 (4)	0.029 (4)	0.038 (4)	0.002 (3)	−0.001 (3)	0.005 (3)
C17	0.056 (5)	0.030 (4)	0.057 (5)	0.008 (4)	0.005 (4)	0.012 (4)
C18	0.052 (5)	0.040 (5)	0.057 (5)	0.024 (4)	0.007 (4)	0.005 (4)
C19	0.042 (5)	0.051 (5)	0.047 (5)	0.019 (4)	0.011 (4)	0.008 (4)
C20	0.032 (4)	0.033 (4)	0.040 (4)	0.008 (3)	0.004 (3)	0.009 (3)
Cl1	0.0469 (13)	0.0574 (14)	0.0617 (14)	0.0199 (10)	0.0162 (11)	−0.0077 (11)
Cl2	0.0386 (12)	0.0390 (11)	0.0702 (15)	−0.0042 (8)	0.0115 (10)	0.0113 (10)
N1	0.025 (3)	0.025 (3)	0.035 (3)	0.005 (2)	−0.005 (3)	0.004 (3)
O1	0.023 (3)	0.058 (4)	0.076 (4)	0.010 (3)	0.005 (3)	0.014 (3)

Geometric parameters (Å, º) top

C1—N1	1.473 (9)	C9—C14	1.408 (10)
C1—C9	1.524 (9)	C9—C10	1.408 (10)
C1—C2	1.556 (10)	C10—C11	1.393 (11)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.507 (10)	C11—C12	1.392 (12)
C2—C3	1.554 (11)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.364 (12)
C3—C4	1.534 (11)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.398 (10)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.555 (11)	C14—Cl1	1.759 (7)
C4—H4A	0.9700	C15—C20	1.398 (10)
C4—H4B	0.9700	C15—C16	1.401 (10)
C5—C6	1.555 (11)	C16—C17	1.372 (11)
C5—H5A	0.9700	C16—Cl2	1.766 (8)
C5—H5B	0.9700	C17—C18	1.399 (12)
C6—C8	1.525 (10)	C17—H17	0.9300
C6—C7	1.547 (10)	C18—C19	1.377 (12)
C6—H6	0.9800	C18—H18	0.9300
C7—N1	1.472 (9)	C19—C20	1.387 (11)
C7—C15	1.531 (10)	C19—H19	0.9300
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.203 (9)	N1—H1A	0.81 (9)

N1—C1—C9	110.5 (5)	O1—C8—C2	124.3 (7)
N1—C1—C2	109.7 (6)	O1—C8—C6	124.1 (7)
C9—C1—C2	111.4 (6)	C2—C8—C6	111.6 (6)
N1—C1—H1	108.4	C14—C9—C10	115.8 (6)
C9—C1—H1	108.4	C14—C9—C1	122.9 (6)
C2—C1—H1	108.4	C10—C9—C1	121.2 (6)
C8—C2—C3	108.7 (6)	C11—C10—C9	121.7 (7)
C8—C2—C1	107.6 (6)	C11—C10—H10	119.1
C3—C2—C1	114.4 (6)	C9—C10—H10	119.1
C8—C2—H2	108.7	C12—C11—C10	120.0 (7)
C3—C2—H2	108.7	C12—C11—H11	120.0
C1—C2—H2	108.7	C10—C11—H11	120.0
C4—C3—C2	115.2 (6)	C13—C12—C11	120.3 (7)
C4—C3—H3A	108.5	C13—C12—H12	119.9
C2—C3—H3A	108.5	C11—C12—H12	119.9
C4—C3—H3B	108.5	C12—C13—C14	119.5 (7)
C2—C3—H3B	108.5	C12—C13—H13	120.2
H3A—C3—H3B	107.5	C14—C13—H13	120.2
C3—C4—C5	112.7 (7)	C13—C14—C9	122.6 (7)
C3—C4—H4A	109.0	C13—C14—Cl1	117.5 (6)
C5—C4—H4A	109.0	C9—C14—Cl1	119.9 (5)
C3—C4—H4B	109.0	C20—C15—C16	116.6 (7)
C5—C4—H4B	109.0	C20—C15—C7	121.6 (6)
H4A—C4—H4B	107.8	C16—C15—C7	121.8 (6)
C6—C5—C4	114.2 (6)	C17—C16—C15	122.8 (7)
C6—C5—H5A	108.7	C17—C16—Cl2	116.5 (6)
C4—C5—H5A	108.7	C15—C16—Cl2	120.7 (6)
C6—C5—H5B	108.7	C16—C17—C18	119.3 (8)
C4—C5—H5B	108.7	C16—C17—H17	120.4
H5A—C5—H5B	107.6	C18—C17—H17	120.4
C8—C6—C7	107.8 (6)	C19—C18—C17	119.4 (7)
C8—C6—C5	107.0 (6)	C19—C18—H18	120.3
C7—C6—C5	115.4 (6)	C17—C18—H18	120.3
C8—C6—H6	108.9	C18—C19—C20	120.7 (8)
C7—C6—H6	108.9	C18—C19—H19	119.7
C5—C6—H6	108.9	C20—C19—H19	119.7
N1—C7—C15	109.7 (5)	C19—C20—C15	121.2 (7)
N1—C7—C6	111.0 (6)	C19—C20—H20	119.4
C15—C7—C6	112.1 (6)	C15—C20—H20	119.4
N1—C7—H7	107.9	C7—N1—C1	113.5 (5)
C15—C7—H7	107.9	C7—N1—H1A	113 (6)
C6—C7—H7	107.9	C1—N1—H1A	110 (6)

N1—C1—C2—C8	−58.3 (7)	C9—C10—C11—C12	1.1 (12)
C9—C1—C2—C8	179.2 (6)	C10—C11—C12—C13	−1.8 (12)
N1—C1—C2—C3	62.6 (8)	C11—C12—C13—C14	2.4 (12)
C9—C1—C2—C3	−60.0 (8)	C12—C13—C14—C9	−2.4 (11)
C8—C2—C3—C4	50.7 (8)	C12—C13—C14—Cl1	179.6 (6)
C1—C2—C3—C4	−69.5 (8)	C10—C9—C14—C13	1.7 (10)
C2—C3—C4—C5	−41.8 (9)	C1—C9—C14—C13	177.8 (7)
C3—C4—C5—C6	44.1 (9)	C10—C9—C14—Cl1	179.6 (5)
C4—C5—C6—C8	−54.4 (8)	C1—C9—C14—Cl1	−4.2 (9)
C4—C5—C6—C7	65.4 (9)	N1—C7—C15—C20	25.3 (9)
C8—C6—C7—N1	55.2 (8)	C6—C7—C15—C20	−98.5 (8)
C5—C6—C7—N1	−64.2 (8)	N1—C7—C15—C16	−153.5 (7)
C8—C6—C7—C15	178.4 (6)	C6—C7—C15—C16	82.6 (8)
C5—C6—C7—C15	59.0 (8)	C20—C15—C16—C17	−0.6 (11)
C3—C2—C8—O1	115.3 (8)	C7—C15—C16—C17	178.3 (7)
C1—C2—C8—O1	−120.3 (8)	C20—C15—C16—Cl2	−178.7 (6)
C3—C2—C8—C6	−63.3 (8)	C7—C15—C16—Cl2	0.2 (10)
C1—C2—C8—C6	61.1 (8)	C15—C16—C17—C18	0.8 (13)
C7—C6—C8—O1	121.9 (8)	Cl2—C16—C17—C18	179.0 (7)
C5—C6—C8—O1	−113.5 (8)	C16—C17—C18—C19	−0.6 (13)
C7—C6—C8—C2	−59.5 (8)	C17—C18—C19—C20	0.1 (13)
C5—C6—C8—C2	65.1 (7)	C18—C19—C20—C15	0.2 (13)
N1—C1—C9—C14	159.5 (6)	C16—C15—C20—C19	0.0 (11)
C2—C1—C9—C14	−78.4 (8)	C7—C15—C20—C19	−178.8 (7)
N1—C1—C9—C10	−24.5 (9)	C15—C7—N1—C1	178.5 (6)
C2—C1—C9—C10	97.6 (8)	C6—C7—N1—C1	−56.9 (8)
C14—C9—C10—C11	−1.0 (11)	C9—C1—N1—C7	−178.9 (6)
C1—C9—C10—C11	−177.3 (7)	C2—C1—N1—C7	58.0 (8)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₉Cl₂NO
M_r	360.26
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.7070 (15), 10.680 (2), 11.000 (2)
α, β, γ (°)	101.78 (3), 92.82 (3), 98.13 (3)
V (Å³)	874.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.32 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.889, 0.928
No. of measured, independent and observed [I > 2σ(I)] reflections	9470, 2949, 2478
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.309, 1.19
No. of reflections	2949
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)	0.70, −0.41

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

Acknowledgements

This research was supported by the second stage of the BK 21 program and Pukyong National University under the 2008 Postdoc program. The authors acknowledge the Department of Chemistry, IIT, Madras, for the X-ray data collection.

References

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