2,4-Bis(2-chloro-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one.

The mol-ecular structure of the title compound, C(20)H(19)Cl(2)NO, reveals chair conformations for both six-membered rings of the bicyclic system. Both 2-chloro-phenyl 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 = 360.26

Triclinic,

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[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.309

S = 1.19

2949 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C20H19Cl2NO	Z = 2
Mr = 360.26	F000 = 376
Triclinic, P1	Dx = 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 = 2.4–28.3º
c = 11.000 (2) Å	µ = 0.38 mm−1
α = 101.78 (3)º	T = 298 (2) K
β = 92.82 (3)º	Rectangular, colourless
γ = 98.13 (3)º	0.32 × 0.25 × 0.20 mm
V = 874.6 (3) Å3

Bruker APEXII CCD area-detector diffractometer	2949 independent reflections
Radiation source: fine-focus sealed tube	2478 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.026
T = 298(2) K	θmax = 25.0º
ω scans	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −8→9
Tmin = 0.889, Tmax = 0.928	k = −12→12
9470 measured reflections	l = −12→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.088	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.309	w = 1/[σ2(Fo2) + (0.0815P)2 + 8.5055P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max < 0.001
2949 reflections	Δρmax = 0.70 e Å−3
221 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 takeninto account individually in the estimation of e.s.d.'s in distances, anglesand torsion angles; correlations between e.s.d.'s in cell parameters are onlyused 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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)