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

In the mol-ecular structure of the title compound, C(20)H(19)Br(2)NO, the fused six-membered heterocyclic and cyclo-hexane rings adopt a twin-chair conformation with equatorial orientations of all the substituents. Both the ortho-bromo substituents of the benzene rings are oriented towards the carbonyl group; the dihedral angle between the ring planes is 29.13 (3)°. In the crystal structure, the N-H group does not participate in any hydrogen bonds.

Related literature

For 3-aza­bicyclo­nonan-9-ones and their significance as bio-active mol­ecules, see: Barker et al. (2005 ▶); Jeyaraman & Avila (1981 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶); Web & Becker (1967 ▶). For a similiar structure see; Parthiban et al. (2008 ▶).

Experimental

Crystal data

C20H19Br2NO

M = 449.18

Triclinic,

a = 7.8389 (3) Å

b = 10.5770 (3) Å

c = 11.0274 (3) Å

α = 101.099 (2)°

β = 93.725 (2)°

γ = 97.399 (1)°

V = 885.94 (5) Å3

Z = 2

Mo Kα radiation

μ = 4.58 mm−1

T = 298 (2) K

0.45 × 0.38 × 0.35 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.232, T max = 0.297 (expected range = 0.157–0.201)

10959 measured reflections

4098 independent reflections

3266 reflections with I > 2σ(I)

R int = 0.017

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.060

S = 1.00

4098 reflections

221 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.58 e Å−3

Δρmin = −0.56 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/S1600536808037501/hb2843sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037501/hb2843Isup2.hkl

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

C20H19Br2NO	Z = 2
Mr = 449.18	F000 = 448
Triclinic, P1	Dx = 1.684 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.8389 (3) Å	Cell parameters from 5642 reflections
b = 10.5770 (3) Å	θ = 2.5–28.2º
c = 11.0274 (3) Å	µ = 4.58 mm−1
α = 101.099 (2)º	T = 298 (2) K
β = 93.725 (2)º	Block, colourless
γ = 97.399 (1)º	0.45 × 0.38 × 0.35 mm
V = 885.94 (5) Å3

Bruker APEXII CCD diffractometer	4098 independent reflections
Radiation source: fine-focus sealed tube	3266 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.017
T = 298(2) K	θmax = 28.3º
ω scans	θmin = 1.9º
Absorption correction: Multi-scan(SADABS; Bruker, 1999)	h = −10→10
Tmin = 0.232, Tmax = 0.297	k = −13→13
10959 measured reflections	l = −14→14

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)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0207P)2 + 0.5638P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.002
4098 reflections	Δρmax = 0.58 e Å−3
221 parameters	Δρmin = −0.56 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 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
Br1	−0.00438 (3)	0.47719 (2)	0.77681 (2)	0.05065 (8)
Br2	0.16949 (3)	1.23193 (3)	1.01448 (2)	0.06070 (9)
C1	0.2124 (2)	0.74756 (18)	0.75331 (18)	0.0301 (4)
H1	0.1437	0.7370	0.8228	0.036*
C2	0.0889 (2)	0.76537 (19)	0.64395 (19)	0.0344 (4)
H2	−0.0049	0.6918	0.6254	0.041*
C3	0.1735 (3)	0.7773 (2)	0.5238 (2)	0.0428 (5)
H3A	0.2294	0.7011	0.4980	0.051*
H3B	0.0839	0.7778	0.4591	0.051*
C4	0.3064 (3)	0.8987 (2)	0.5360 (2)	0.0432 (5)
H4A	0.4119	0.8865	0.5806	0.052*
H4B	0.3333	0.9102	0.4539	0.052*
C5	0.2434 (3)	1.0214 (2)	0.60396 (19)	0.0392 (5)
H5A	0.1647	1.0500	0.5468	0.047*
H5B	0.3418	1.0895	0.6280	0.047*
C6	0.1515 (2)	1.00528 (19)	0.72040 (18)	0.0331 (4)
H6	0.0967	1.0828	0.7479	0.040*
C7	0.2692 (2)	0.98341 (18)	0.83118 (17)	0.0294 (4)
H7	0.1987	0.9747	0.9001	0.035*
C8	0.0132 (2)	0.8886 (2)	0.68529 (18)	0.0342 (4)
C9	0.3014 (2)	0.62834 (18)	0.72007 (17)	0.0304 (4)
C10	0.4692 (3)	0.6383 (2)	0.6847 (2)	0.0389 (5)
H10	0.5265	0.7194	0.6796	0.047*
C11	0.5525 (3)	0.5302 (2)	0.6570 (2)	0.0495 (6)
H11	0.6641	0.5392	0.6328	0.059*
C12	0.4711 (3)	0.4095 (2)	0.6651 (2)	0.0556 (6)
H12	0.5280	0.3371	0.6472	0.067*
C13	0.3055 (3)	0.3958 (2)	0.6995 (2)	0.0482 (6)
H13	0.2496	0.3142	0.7047	0.058*
C14	0.2228 (3)	0.50413 (19)	0.72632 (19)	0.0350 (4)
C15	0.4125 (2)	1.09742 (18)	0.87430 (17)	0.0290 (4)
C16	0.3860 (3)	1.21258 (19)	0.95107 (18)	0.0337 (4)
C17	0.5159 (3)	1.3181 (2)	0.9863 (2)	0.0436 (5)
H17	0.4946	1.3938	1.0380	0.052*
C18	0.6757 (3)	1.3104 (2)	0.9446 (2)	0.0499 (6)
H18	0.7629	1.3812	0.9670	0.060*
C19	0.7071 (3)	1.1976 (2)	0.8696 (2)	0.0482 (6)
H19	0.8161	1.1920	0.8421	0.058*
C20	0.5772 (3)	1.0923 (2)	0.8347 (2)	0.0381 (5)
H20	0.6003	1.0166	0.7839	0.046*
N1	0.3422 (2)	0.86343 (15)	0.79409 (16)	0.0304 (4)
O1	−0.13950 (19)	0.89419 (17)	0.68681 (16)	0.0521 (4)
H1A	0.407 (3)	0.851 (2)	0.850 (2)	0.040 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.04366 (13)	0.03775 (13)	0.06740 (17)	−0.00469 (9)	0.01281 (11)	0.00737 (11)
Br2	0.05389 (15)	0.06429 (18)	0.05949 (17)	0.02181 (12)	0.01497 (12)	−0.01039 (13)
C1	0.0296 (9)	0.0256 (10)	0.0349 (10)	0.0042 (7)	0.0038 (8)	0.0056 (8)
C2	0.0286 (9)	0.0300 (10)	0.0415 (11)	0.0019 (8)	−0.0038 (8)	0.0035 (9)
C3	0.0511 (13)	0.0398 (12)	0.0351 (11)	0.0125 (10)	−0.0022 (10)	−0.0001 (9)
C4	0.0505 (13)	0.0492 (13)	0.0325 (11)	0.0104 (10)	0.0097 (9)	0.0107 (10)
C5	0.0441 (11)	0.0369 (12)	0.0386 (12)	0.0063 (9)	−0.0008 (9)	0.0138 (9)
C6	0.0326 (10)	0.0299 (10)	0.0371 (11)	0.0102 (8)	0.0012 (8)	0.0046 (8)
C7	0.0300 (9)	0.0276 (10)	0.0302 (10)	0.0044 (7)	0.0033 (7)	0.0049 (8)
C8	0.0310 (9)	0.0405 (12)	0.0327 (11)	0.0088 (8)	−0.0003 (8)	0.0100 (9)
C9	0.0335 (9)	0.0278 (10)	0.0295 (10)	0.0060 (8)	0.0003 (8)	0.0046 (8)
C10	0.0357 (10)	0.0380 (12)	0.0448 (12)	0.0081 (9)	0.0059 (9)	0.0104 (9)
C11	0.0417 (12)	0.0553 (15)	0.0575 (15)	0.0220 (11)	0.0123 (11)	0.0135 (12)
C12	0.0657 (16)	0.0446 (14)	0.0637 (16)	0.0311 (12)	0.0140 (13)	0.0109 (12)
C13	0.0608 (15)	0.0297 (12)	0.0551 (14)	0.0101 (10)	0.0065 (11)	0.0083 (10)
C14	0.0371 (10)	0.0304 (10)	0.0362 (11)	0.0041 (8)	0.0025 (8)	0.0038 (8)
C15	0.0314 (9)	0.0280 (10)	0.0284 (10)	0.0053 (8)	0.0005 (7)	0.0079 (8)
C16	0.0403 (10)	0.0322 (11)	0.0297 (10)	0.0100 (8)	0.0010 (8)	0.0062 (8)
C17	0.0646 (15)	0.0278 (11)	0.0353 (12)	0.0034 (10)	−0.0054 (10)	0.0047 (9)
C18	0.0547 (14)	0.0427 (13)	0.0455 (13)	−0.0154 (11)	−0.0072 (11)	0.0108 (11)
C19	0.0346 (11)	0.0573 (15)	0.0500 (14)	−0.0043 (10)	0.0028 (10)	0.0117 (12)
C20	0.0337 (10)	0.0375 (11)	0.0411 (12)	0.0048 (9)	0.0047 (9)	0.0029 (9)
N1	0.0292 (8)	0.0249 (8)	0.0362 (9)	0.0055 (6)	−0.0050 (7)	0.0053 (7)
O1	0.0292 (7)	0.0588 (11)	0.0693 (11)	0.0119 (7)	0.0028 (7)	0.0120 (9)

Br1—C14	1.903 (2)	C7—H7	0.9800
Br2—C16	1.897 (2)	C8—O1	1.207 (2)
C1—N1	1.465 (2)	C9—C10	1.393 (3)
C1—C9	1.515 (3)	C9—C14	1.394 (3)
C1—C2	1.552 (3)	C10—C11	1.382 (3)
C1—H1	0.9800	C10—H10	0.9300
C2—C8	1.505 (3)	C11—C12	1.373 (4)
C2—C3	1.539 (3)	C11—H11	0.9300
C2—H2	0.9800	C12—C13	1.373 (3)
C3—C4	1.524 (3)	C12—H12	0.9300
C3—H3A	0.9700	C13—C14	1.381 (3)
C3—H3B	0.9700	C13—H13	0.9300
C4—C5	1.525 (3)	C15—C20	1.393 (3)
C4—H4A	0.9700	C15—C16	1.391 (3)
C4—H4B	0.9700	C16—C17	1.387 (3)
C5—C6	1.539 (3)	C17—C18	1.369 (3)
C5—H5A	0.9700	C17—H17	0.9300
C5—H5B	0.9700	C18—C19	1.375 (4)
C6—C8	1.506 (3)	C18—H18	0.9300
C6—C7	1.554 (3)	C19—C20	1.385 (3)
C6—H6	0.9800	C19—H19	0.9300
C7—N1	1.457 (2)	C20—H20	0.9300
C7—C15	1.518 (2)	N1—H1A	0.81 (2)
N1—C1—C9	109.63 (15)	O1—C8—C2	124.48 (19)
N1—C1—C2	110.38 (16)	O1—C8—C6	123.98 (19)
C9—C1—C2	112.32 (16)	C2—C8—C6	111.51 (16)
N1—C1—H1	108.1	C10—C9—C14	116.51 (18)
C9—C1—H1	108.1	C10—C9—C1	121.26 (17)
C2—C1—H1	108.1	C14—C9—C1	122.21 (17)
C8—C2—C3	107.21 (17)	C11—C10—C9	121.5 (2)
C8—C2—C1	107.83 (16)	C11—C10—H10	119.3
C3—C2—C1	115.42 (16)	C9—C10—H10	119.3
C8—C2—H2	108.7	C12—C11—C10	120.3 (2)
C3—C2—H2	108.7	C12—C11—H11	119.9
C1—C2—H2	108.7	C10—C11—H11	119.9
C4—C3—C2	114.03 (17)	C13—C12—C11	119.9 (2)
C4—C3—H3A	108.7	C13—C12—H12	120.1
C2—C3—H3A	108.7	C11—C12—H12	120.1
C4—C3—H3B	108.7	C12—C13—C14	119.5 (2)
C2—C3—H3B	108.7	C12—C13—H13	120.3
H3A—C3—H3B	107.6	C14—C13—H13	120.3
C5—C4—C3	112.67 (18)	C13—C14—C9	122.3 (2)
C5—C4—H4A	109.1	C13—C14—Br1	116.76 (16)
C3—C4—H4A	109.1	C9—C14—Br1	120.89 (15)
C5—C4—H4B	109.1	C20—C15—C16	116.80 (18)
C3—C4—H4B	109.1	C20—C15—C7	120.81 (17)
H4A—C4—H4B	107.8	C16—C15—C7	122.36 (17)
C4—C5—C6	114.82 (17)	C17—C16—C15	122.0 (2)
C4—C5—H5A	108.6	C17—C16—Br2	116.64 (16)
C6—C5—H5A	108.6	C15—C16—Br2	121.32 (15)
C4—C5—H5B	108.6	C18—C17—C16	119.7 (2)
C6—C5—H5B	108.6	C18—C17—H17	120.2
H5A—C5—H5B	107.5	C16—C17—H17	120.2
C8—C6—C5	108.13 (16)	C17—C18—C19	119.9 (2)
C8—C6—C7	107.18 (16)	C17—C18—H18	120.0
C5—C6—C7	115.25 (16)	C19—C18—H18	120.0
C8—C6—H6	108.7	C18—C19—C20	120.3 (2)
C5—C6—H6	108.7	C18—C19—H19	119.9
C7—C6—H6	108.7	C20—C19—H19	119.9
N1—C7—C15	110.21 (15)	C19—C20—C15	121.3 (2)
N1—C7—C6	109.31 (15)	C19—C20—H20	119.3
C15—C7—C6	111.09 (15)	C15—C20—H20	119.3
N1—C7—H7	108.7	C7—N1—C1	113.89 (15)
C15—C7—H7	108.7	C7—N1—H1A	111.0 (16)
C6—C7—H7	108.7	C1—N1—H1A	108.6 (16)
N1—C1—C2—C8	−55.2 (2)	C9—C10—C11—C12	−0.6 (4)
C9—C1—C2—C8	−177.89 (16)	C10—C11—C12—C13	0.7 (4)
N1—C1—C2—C3	64.6 (2)	C11—C12—C13—C14	−0.3 (4)
C9—C1—C2—C3	−58.1 (2)	C12—C13—C14—C9	−0.2 (3)
C8—C2—C3—C4	55.1 (2)	C12—C13—C14—Br1	−178.65 (19)
C1—C2—C3—C4	−65.0 (2)	C10—C9—C14—C13	0.2 (3)
C2—C3—C4—C5	−45.4 (3)	C1—C9—C14—C13	−178.10 (19)
C3—C4—C5—C6	43.4 (3)	C10—C9—C14—Br1	178.65 (15)
C4—C5—C6—C8	−51.3 (2)	C1—C9—C14—Br1	0.3 (3)
C4—C5—C6—C7	68.6 (2)	N1—C7—C15—C20	23.6 (2)
C8—C6—C7—N1	58.74 (19)	C6—C7—C15—C20	−97.7 (2)
C5—C6—C7—N1	−61.6 (2)	N1—C7—C15—C16	−158.48 (18)
C8—C6—C7—C15	−179.43 (15)	C6—C7—C15—C16	80.2 (2)
C5—C6—C7—C15	60.2 (2)	C20—C15—C16—C17	0.5 (3)
C3—C2—C8—O1	113.0 (2)	C7—C15—C16—C17	−177.53 (18)
C1—C2—C8—O1	−122.1 (2)	C20—C15—C16—Br2	−178.76 (15)
C3—C2—C8—C6	−64.9 (2)	C7—C15—C16—Br2	3.2 (3)
C1—C2—C8—C6	59.9 (2)	C15—C16—C17—C18	0.3 (3)
C5—C6—C8—O1	−114.9 (2)	Br2—C16—C17—C18	179.52 (17)
C7—C6—C8—O1	120.3 (2)	C16—C17—C18—C19	−0.9 (3)
C5—C6—C8—C2	63.1 (2)	C17—C18—C19—C20	0.8 (4)
C7—C6—C8—C2	−61.7 (2)	C18—C19—C20—C15	0.0 (3)
N1—C1—C9—C10	−24.4 (3)	C16—C15—C20—C19	−0.6 (3)
C2—C1—C9—C10	98.7 (2)	C7—C15—C20—C19	177.4 (2)
N1—C1—C9—C14	153.82 (18)	C15—C7—N1—C1	178.86 (15)
C2—C1—C9—C14	−83.1 (2)	C6—C7—N1—C1	−58.8 (2)
C14—C9—C10—C11	0.2 (3)	C9—C1—N1—C7	−178.59 (16)
C1—C9—C10—C11	178.5 (2)	C2—C1—N1—C7	57.2 (2)