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

In the mol-ecular structure of the title compound, C(20)H(19)Cl(2)NO, the bicyclic system adopts a twin-chair conformation with equatorial orientations of both substituents. The dihedral angle between the aromatic rings is 43.60 (2)° with respect to each other. The crystal structure is stabilized by weak N-H⋯O and strong C-H⋯O inter-actions.

Related literature

For the biological significance, synthesis and stereochemistry of 3-aza­bicyclo­nonan-9-ones, see: Jeyaraman & Avila (1981 ▶). For similiar structures, see: Parthiban et al. (2008a ▶,b ▶,c ▶,d ▶,e ▶). For puckering parameters, see: Web & Becker (1967 ▶); Cremer & Pople (1975 ▶).

Experimental

Crystal data

C20H19Cl2NO

M = 360.26

Orthorhombic,

a = 6.9950 (14) Å

b = 12.180 (2) Å

c = 20.770 (4) Å

V = 1769.6 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.37 mm−1

T = 298 K

0.31 × 0.25 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.875, T max = 0.922

23614 measured reflections

4284 independent reflections

2762 reflections with I > 2σ(I)

R int = 0.046

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.084

S = 1.01

4284 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Absolute structure: Flack (1983 ▶), 1756 Friedel pairs

Flack parameter: −0.05 (5)

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009945/gw2060sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009945/gw2060Isup2.hkl

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

C20H19Cl2NO	F(000) = 752
Mr = 360.26	Dx = 1.352 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5421 reflections
a = 6.9950 (14) Å	θ = 2.6–22.5°
b = 12.180 (2) Å	µ = 0.37 mm−1
c = 20.770 (4) Å	T = 298 K
V = 1769.6 (6) Å3	Block, colourless
Z = 4	0.31 × 0.25 × 0.22 mm

Bruker APEXII CCD area-detector diffractometer	4284 independent reflections
Radiation source: fine-focus sealed tube	2762 reflections with I > 2σ(I)
graphite	Rint = 0.046
ω scans	θmax = 28.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→9
Tmin = 0.875, Tmax = 0.922	k = −16→16
23614 measured reflections	l = −27→16

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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.084	w = 1/[σ2(Fo2) + (0.0341P)2 + 0.181P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.002
4284 reflections	Δρmax = 0.16 e Å−3
221 parameters	Δρmin = −0.25 e Å−3
0 restraints	Absolute structure: Flack (1983), 1756 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.05 (5)

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 andgoodness of fit S are based on F2, conventional R-factors R are basedon F, with F set to zero for negative F2. The threshold expression ofF2 > σ(F2) is used only for calculating R-factors(gt) etc. and isnot relevant to the choice of reflections for refinement. R-factors basedon 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	0.1155 (3)	0.91094 (15)	0.96470 (9)	0.0351 (5)
H1	0.0839	0.8690	1.0035	0.042*
C2	−0.0754 (3)	0.94712 (17)	0.93253 (10)	0.0425 (5)
H2	−0.1483	0.9910	0.9635	0.051*
C3	−0.0574 (3)	1.01301 (18)	0.86920 (11)	0.0522 (6)
H3A	−0.1829	1.0398	0.8571	0.063*
H3B	0.0236	1.0763	0.8768	0.063*
C4	0.0248 (4)	0.94740 (18)	0.81344 (10)	0.0517 (6)
H4A	0.0035	0.9874	0.7737	0.062*
H4B	0.1617	0.9400	0.8193	0.062*
C5	−0.0633 (3)	0.83391 (19)	0.80751 (10)	0.0493 (6)
H5A	0.0141	0.7906	0.7782	0.059*
H5B	−0.1894	0.8411	0.7886	0.059*
C6	−0.0815 (3)	0.77124 (16)	0.87165 (10)	0.0405 (5)
H6	−0.1583	0.7050	0.8646	0.049*
C7	0.1088 (3)	0.73829 (16)	0.90524 (9)	0.0373 (5)
H7	0.0767	0.7017	0.9459	0.045*
C8	−0.1852 (3)	0.84501 (17)	0.91799 (9)	0.0417 (5)
C9	0.2390 (3)	1.00628 (15)	0.98456 (9)	0.0353 (5)
C10	0.3661 (3)	1.05578 (17)	0.94271 (10)	0.0485 (6)
H10	0.3780	1.0292	0.9009	0.058*
C11	0.4763 (4)	1.14476 (18)	0.96219 (12)	0.0589 (7)
H11	0.5609	1.1773	0.9334	0.071*
C12	0.4608 (3)	1.18510 (18)	1.02405 (11)	0.0514 (6)
H12	0.5330	1.2452	1.0372	0.062*
C13	0.3367 (3)	1.13481 (15)	1.06568 (10)	0.0430 (5)
C14	0.2249 (3)	1.04678 (16)	1.04695 (9)	0.0399 (5)
H14	0.1404	1.0148	1.0760	0.048*
C15	0.2255 (3)	0.65933 (15)	0.86531 (10)	0.0388 (5)
C16	0.2048 (3)	0.54727 (17)	0.87560 (12)	0.0543 (6)
H16	0.1230	0.5222	0.9077	0.065*
C17	0.3056 (4)	0.47232 (18)	0.83825 (15)	0.0679 (8)
H17	0.2895	0.3975	0.8453	0.081*
C18	0.4283 (4)	0.5073 (2)	0.79115 (13)	0.0619 (7)
H18	0.4961	0.4570	0.7664	0.074*
C19	0.4494 (3)	0.61781 (19)	0.78124 (12)	0.0514 (6)
C20	0.3510 (3)	0.69381 (17)	0.81787 (10)	0.0457 (5)
H20	0.3692	0.7684	0.8106	0.055*
Cl1	0.32230 (11)	1.18133 (5)	1.14500 (3)	0.0681 (2)
Cl2	0.60281 (11)	0.66335 (6)	0.72080 (3)	0.0794 (2)
N1	0.2172 (3)	0.83753 (13)	0.92051 (8)	0.0358 (4)
O1	−0.3405 (2)	0.82264 (14)	0.94107 (7)	0.0583 (4)
H1A	0.324 (3)	0.8184 (15)	0.9342 (9)	0.033 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0369 (12)	0.0377 (11)	0.0307 (9)	−0.0016 (9)	0.0059 (9)	−0.0005 (9)
C2	0.0360 (12)	0.0472 (12)	0.0443 (12)	0.0048 (10)	0.0048 (10)	−0.0061 (10)
C3	0.0502 (15)	0.0476 (13)	0.0587 (15)	0.0068 (11)	−0.0079 (12)	0.0076 (11)
C4	0.0549 (14)	0.0579 (14)	0.0421 (12)	−0.0040 (12)	−0.0058 (11)	0.0153 (11)
C5	0.0462 (14)	0.0647 (14)	0.0370 (11)	0.0005 (12)	−0.0065 (10)	0.0008 (11)
C6	0.0358 (12)	0.0435 (12)	0.0421 (12)	−0.0079 (10)	−0.0046 (10)	−0.0016 (9)
C7	0.0386 (12)	0.0371 (11)	0.0363 (11)	−0.0059 (10)	−0.0013 (9)	0.0008 (9)
C8	0.0307 (12)	0.0577 (13)	0.0366 (11)	0.0013 (11)	−0.0007 (10)	0.0090 (10)
C9	0.0347 (11)	0.0353 (11)	0.0359 (11)	0.0048 (9)	0.0008 (9)	−0.0016 (9)
C10	0.0553 (14)	0.0469 (12)	0.0433 (12)	−0.0088 (12)	0.0088 (11)	−0.0102 (10)
C11	0.0656 (16)	0.0530 (15)	0.0580 (14)	−0.0152 (13)	0.0154 (13)	−0.0035 (12)
C12	0.0536 (15)	0.0388 (12)	0.0619 (15)	−0.0075 (12)	−0.0048 (12)	−0.0081 (11)
C13	0.0500 (13)	0.0381 (11)	0.0409 (11)	0.0058 (10)	−0.0065 (11)	−0.0082 (9)
C14	0.0406 (12)	0.0422 (11)	0.0368 (11)	0.0054 (10)	0.0017 (9)	0.0006 (9)
C15	0.0396 (12)	0.0355 (11)	0.0412 (11)	−0.0008 (9)	−0.0085 (10)	−0.0074 (9)
C16	0.0499 (15)	0.0423 (13)	0.0708 (16)	−0.0074 (12)	−0.0046 (12)	−0.0040 (11)
C17	0.0720 (19)	0.0362 (13)	0.096 (2)	0.0028 (13)	−0.0140 (17)	−0.0134 (13)
C18	0.0565 (16)	0.0550 (16)	0.0743 (18)	0.0137 (13)	−0.0127 (15)	−0.0296 (14)
C19	0.0460 (14)	0.0588 (15)	0.0494 (13)	0.0060 (11)	−0.0049 (11)	−0.0193 (11)
C20	0.0507 (13)	0.0386 (11)	0.0477 (12)	0.0012 (11)	−0.0006 (11)	−0.0109 (10)
Cl1	0.0959 (5)	0.0649 (4)	0.0435 (3)	−0.0048 (4)	−0.0084 (3)	−0.0171 (3)
Cl2	0.0814 (5)	0.0891 (5)	0.0675 (4)	0.0069 (4)	0.0235 (4)	−0.0261 (4)
N1	0.0305 (10)	0.0393 (9)	0.0376 (9)	0.0018 (9)	−0.0019 (8)	−0.0052 (8)
O1	0.0363 (9)	0.0793 (11)	0.0593 (10)	−0.0063 (9)	0.0087 (8)	0.0071 (9)

C1—N1	1.465 (2)	C9—C10	1.382 (3)
C1—C9	1.505 (3)	C9—C14	1.390 (3)
C1—C2	1.557 (3)	C10—C11	1.390 (3)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.493 (3)	C11—C12	1.380 (3)
C2—C3	1.546 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.369 (3)
C3—C4	1.520 (3)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.383 (3)
C3—H3B	0.9700	C13—Cl1	1.745 (2)
C4—C5	1.518 (3)	C14—H14	0.9300
C4—H4A	0.9700	C15—C16	1.389 (3)
C4—H4B	0.9700	C15—C20	1.385 (3)
C5—C6	1.541 (3)	C16—C17	1.390 (3)
C5—H5A	0.9700	C16—H16	0.9300
C5—H5B	0.9700	C17—C18	1.370 (4)
C6—C8	1.503 (3)	C17—H17	0.9300
C6—C7	1.556 (3)	C18—C19	1.369 (3)
C6—H6	0.9800	C18—H18	0.9300
C7—N1	1.462 (3)	C19—C20	1.382 (3)
C7—C15	1.510 (3)	C19—Cl2	1.742 (3)
C7—H7	0.9800	C20—H20	0.9300
C8—O1	1.218 (2)	N1—H1A	0.83 (2)
N1—C1—C9	111.35 (16)	O1—C8—C2	124.5 (2)
N1—C1—C2	108.66 (16)	O1—C8—C6	123.3 (2)
C9—C1—C2	113.05 (16)	C2—C8—C6	112.28 (17)
N1—C1—H1	107.9	C10—C9—C14	118.52 (19)
C9—C1—H1	107.9	C10—C9—C1	122.25 (18)
C2—C1—H1	107.9	C14—C9—C1	119.23 (18)
C8—C2—C3	107.59 (18)	C9—C10—C11	120.9 (2)
C8—C2—C1	107.01 (16)	C9—C10—H10	119.5
C3—C2—C1	116.25 (17)	C11—C10—H10	119.5
C8—C2—H2	108.6	C12—C11—C10	120.3 (2)
C3—C2—H2	108.6	C12—C11—H11	119.8
C1—C2—H2	108.6	C10—C11—H11	119.8
C4—C3—C2	113.96 (17)	C13—C12—C11	118.6 (2)
C4—C3—H3A	108.8	C13—C12—H12	120.7
C2—C3—H3A	108.8	C11—C12—H12	120.7
C4—C3—H3B	108.8	C12—C13—C14	121.8 (2)
C2—C3—H3B	108.8	C12—C13—Cl1	119.18 (17)
H3A—C3—H3B	107.7	C14—C13—Cl1	118.97 (16)
C5—C4—C3	112.78 (19)	C13—C14—C9	119.79 (19)
C5—C4—H4A	109.0	C13—C14—H14	120.1
C3—C4—H4A	109.0	C9—C14—H14	120.1
C5—C4—H4B	109.0	C16—C15—C20	118.3 (2)
C3—C4—H4B	109.0	C16—C15—C7	119.01 (19)
H4A—C4—H4B	107.8	C20—C15—C7	122.72 (18)
C4—C5—C6	114.49 (17)	C15—C16—C17	120.4 (2)
C4—C5—H5A	108.6	C15—C16—H16	119.8
C6—C5—H5A	108.6	C17—C16—H16	119.8
C4—C5—H5B	108.6	C18—C17—C16	120.8 (2)
C6—C5—H5B	108.6	C18—C17—H17	119.6
H5A—C5—H5B	107.6	C16—C17—H17	119.6
C8—C6—C5	107.32 (17)	C19—C18—C17	118.7 (2)
C8—C6—C7	106.25 (16)	C19—C18—H18	120.6
C5—C6—C7	116.39 (17)	C17—C18—H18	120.6
C8—C6—H6	108.9	C18—C19—C20	121.5 (2)
C5—C6—H6	108.9	C18—C19—Cl2	119.17 (19)
C7—C6—H6	108.9	C20—C19—Cl2	119.36 (18)
N1—C7—C15	111.44 (16)	C19—C20—C15	120.3 (2)
N1—C7—C6	109.14 (16)	C19—C20—H20	119.9
C15—C7—C6	112.37 (16)	C15—C20—H20	119.9
N1—C7—H7	107.9	C7—N1—C1	112.88 (15)
C15—C7—H7	107.9	C7—N1—H1A	108.0 (14)
C6—C7—H7	107.9	C1—N1—H1A	113.0 (14)
N1—C1—C2—C8	58.1 (2)	C1—C9—C10—C11	179.1 (2)
C9—C1—C2—C8	−177.77 (16)	C9—C10—C11—C12	0.2 (4)
N1—C1—C2—C3	−62.1 (2)	C10—C11—C12—C13	0.8 (4)
C9—C1—C2—C3	62.0 (2)	C11—C12—C13—C14	−1.3 (3)
C8—C2—C3—C4	−53.3 (2)	C11—C12—C13—Cl1	177.49 (19)
C1—C2—C3—C4	66.6 (3)	C12—C13—C14—C9	0.9 (3)
C2—C3—C4—C5	45.2 (3)	Cl1—C13—C14—C9	−177.89 (16)
C3—C4—C5—C6	−45.3 (3)	C10—C9—C14—C13	0.0 (3)
C4—C5—C6—C8	52.9 (2)	C1—C9—C14—C13	−179.61 (17)
C4—C5—C6—C7	−65.9 (2)	N1—C7—C15—C16	143.69 (19)
C8—C6—C7—N1	−58.4 (2)	C6—C7—C15—C16	−93.5 (2)
C5—C6—C7—N1	60.9 (2)	N1—C7—C15—C20	−37.3 (3)
C8—C6—C7—C15	177.42 (16)	C6—C7—C15—C20	85.5 (2)
C5—C6—C7—C15	−63.2 (2)	C20—C15—C16—C17	−1.1 (3)
C3—C2—C8—O1	−116.6 (2)	C7—C15—C16—C17	177.9 (2)
C1—C2—C8—O1	117.8 (2)	C15—C16—C17—C18	0.7 (4)
C3—C2—C8—C6	63.9 (2)	C16—C17—C18—C19	−0.3 (4)
C1—C2—C8—C6	−61.7 (2)	C17—C18—C19—C20	0.5 (4)
C5—C6—C8—O1	117.0 (2)	C17—C18—C19—Cl2	−179.20 (19)
C7—C6—C8—O1	−117.9 (2)	C18—C19—C20—C15	−1.0 (4)
C5—C6—C8—C2	−63.6 (2)	Cl2—C19—C20—C15	178.72 (16)
C7—C6—C8—C2	61.6 (2)	C16—C15—C20—C19	1.3 (3)
N1—C1—C9—C10	36.4 (3)	C7—C15—C20—C19	−177.8 (2)
C2—C1—C9—C10	−86.3 (2)	C15—C7—N1—C1	−174.09 (16)
N1—C1—C9—C14	−143.97 (18)	C6—C7—N1—C1	61.2 (2)
C2—C1—C9—C14	93.4 (2)	C9—C1—N1—C7	174.24 (16)
C14—C9—C10—C11	−0.6 (3)	C2—C1—N1—C7	−60.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.83 (2)	2.35 (2)	3.129 (3)	155.4 (18)
C7—H7···O1ii	0.98	2.44	3.296 (2)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.83 (2)	2.35 (2)	3.129 (3)	155.4 (18)
C7—H7⋯O1ii	0.98	2.44	3.296 (2)	146

Symmetry codes: (i) ; (ii) .