2,4-Bis(4-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 mol-ecule exists in a twin-chair conformation with equatorial dispositions of the 4-chloro-phenyl 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 inter-actions, 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 = 360.26

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.135

S = 1.02

4997 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.42 e Å−3

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/S160053680900590X/bq2124sup1.cif

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

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

C20H19Cl2NO	F(000) = 752
Mr = 360.26	Dx = 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

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

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(Fo2) + (0.0602P)2 + 0.4485P] where P = (Fo2 + 2Fc2)/3
4997 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.42 e Å−3

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 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	0.33305 (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)*

	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)

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)

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)

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) .