2,4-Bis(2-bromo-phen-yl)-7-tert-pentyl-3-aza-bicyclo-[3.3.1]nonan-9-one.

The title compound, C(25)H(29)Br(2)NO, is a tert-pentyl analog of 2,4-bis-(2-bromo-phen-yl)-3-aza-bicyclo-[3.3.1]nonan-9-one [Par-thiban et al. (2008 ▶). Acta Cryst. E64, o2385]. Similar to its analog, the title compound exists in a twin-chair conformation with an equatorial orientation of the 2-bromo-phenyl groups. The benzene rings are inclined to each other at a dihedral angle of 29.6 (3)°. The tert-pentyl group on the cyclo-hexa-none ring also adopts an exocyclic equatorial disposition.

Related literature

For the synthesis, stereochemistry and biological activity of 3-aza­bicyclo­[3.3.1]nonan-9-ones, see: Park et al. (2011 ▶, 2012a ▶). For the crystal structure of closely related compound, see: Parthiban et al. (2008 ▶). For examples of aza­bicycles with different conformations, see: Parthiban et al. (2010 ▶); Park et al. (2012b ▶); Padegimas & Kovacic (1972 ▶).

Experimental

Crystal data

C25H29Br2NO

M = 519.31

Triclinic,

a = 7.7342 (7) Å

b = 10.6409 (10) Å

c = 15.0924 (12) Å

α = 105.856 (4)°

β = 101.242 (4)°

γ = 97.112 (4)°

V = 1151.08 (18) Å3

Z = 2

Mo Kα radiation

μ = 3.54 mm−1

T = 298 K

0.18 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.569, T max = 0.719

16189 measured reflections

6006 independent reflections

3081 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.212

S = 1.02

6006 reflections

259 parameters

1 restraint

H-atom parameters constrained

Δρmax = 1.24 e Å−3

Δρmin = −1.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 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 datablock(s) global, I. DOI: 10.1107/S1600536812039128/cv5341sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812039128/cv5341Isup2.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039128/cv5341Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812039128/cv5341Isup4.cml

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

C25H29Br2NO	Z = 2
Mr = 519.31	F(000) = 528
Triclinic, P1	Dx = 1.498 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7342 (7) Å	Cell parameters from 4160 reflections
b = 10.6409 (10) Å	θ = 2.7–22.8°
c = 15.0924 (12) Å	µ = 3.54 mm−1
α = 105.856 (4)°	T = 298 K
β = 101.242 (4)°	Prism, colourless
γ = 97.112 (4)°	0.18 × 0.15 × 0.10 mm
V = 1151.08 (18) Å3

Bruker APEXII CCD area-detector diffractometer	6006 independent reflections
Radiation source: fine-focus sealed tube	3081 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
phi and ω scans	θmax = 29.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −10→10
Tmin = 0.569, Tmax = 0.719	k = −14→14
16189 measured reflections	l = −20→19

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.212	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.117P)2] where P = (Fo2 + 2Fc2)/3
6006 reflections	(Δ/σ)max = 0.001
259 parameters	Δρmax = 1.24 e Å−3
1 restraint	Δρmin = −1.26 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 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	0.86819 (8)	0.90205 (5)	0.32088 (5)	0.0717 (3)
Br2	0.85323 (8)	0.28410 (7)	0.51276 (4)	0.0732 (3)
C1	0.6565 (6)	0.6164 (4)	0.3068 (3)	0.0411 (10)
H1	0.7614	0.6679	0.3573	0.049*
C2	0.7228 (6)	0.5383 (4)	0.2223 (3)	0.0440 (11)
H2	0.8022	0.6010	0.2042	0.053*
C3	0.5766 (7)	0.4547 (4)	0.1333 (3)	0.0486 (12)
H3A	0.4990	0.5124	0.1143	0.058*
H3B	0.6342	0.4219	0.0822	0.058*
C4	0.4601 (7)	0.3360 (4)	0.1455 (3)	0.0456 (11)
H4	0.3820	0.3730	0.1857	0.055*
C5	0.5749 (7)	0.2611 (4)	0.1995 (3)	0.0474 (12)
H5A	0.6321	0.2059	0.1558	0.057*
H5B	0.4959	0.2021	0.2195	0.057*
C6	0.7214 (6)	0.3469 (4)	0.2870 (3)	0.0441 (11)
H6	0.7977	0.2894	0.3093	0.053*
C7	0.6514 (6)	0.4244 (4)	0.3698 (3)	0.0408 (10)
H7	0.7552	0.4716	0.4223	0.049*
C8	0.8320 (7)	0.4438 (4)	0.2566 (3)	0.0462 (11)
C9	0.5400 (6)	0.7115 (4)	0.2822 (3)	0.0405 (10)
C10	0.6147 (7)	0.8408 (4)	0.2862 (3)	0.0461 (11)
C11	0.5088 (10)	0.9304 (5)	0.2667 (4)	0.0670 (16)
H11	0.5618	1.0158	0.2708	0.080*
C12	0.3248 (9)	0.8927 (6)	0.2414 (5)	0.0755 (18)
H12	0.2527	0.9530	0.2298	0.091*
C13	0.2472 (8)	0.7627 (6)	0.2332 (4)	0.0676 (16)
H13	0.1235	0.7341	0.2130	0.081*
C14	0.3574 (7)	0.6776 (5)	0.2555 (4)	0.0531 (13)
H14	0.3042	0.5925	0.2521	0.064*
C15	0.5335 (6)	0.3345 (4)	0.4043 (3)	0.0384 (10)
C16	0.3459 (6)	0.3148 (5)	0.3759 (3)	0.0483 (11)
H16	0.2941	0.3628	0.3382	0.058*
C17	0.2358 (8)	0.2263 (6)	0.4020 (4)	0.0596 (14)
H17	0.1119	0.2140	0.3809	0.072*
C18	0.3103 (8)	0.1554 (5)	0.4598 (4)	0.0586 (14)
H18	0.2364	0.0954	0.4773	0.070*
C19	0.4926 (8)	0.1744 (4)	0.4908 (3)	0.0509 (12)
H19	0.5431	0.1276	0.5298	0.061*
C20	0.6015 (6)	0.2631 (4)	0.4641 (3)	0.0415 (10)
N1	0.5541 (5)	0.5240 (3)	0.3436 (3)	0.0413 (9)
H1A	0.4463	0.5282	0.3493	0.050*
O1	0.9910 (5)	0.4487 (4)	0.2582 (3)	0.0695 (10)
C21	0.3326 (9)	0.2448 (5)	0.0486 (4)	0.0732 (18)
C24	0.2293 (15)	0.1222 (10)	0.0634 (7)	0.155 (4)
H24A	0.3131	0.0784	0.0950	0.186*
H24B	0.1656	0.0598	0.0023	0.186*
C22	0.1993 (13)	0.3238 (9)	0.0052 (6)	0.151 (5)
H22A	0.1380	0.2718	−0.0585	0.226*
H22B	0.2649	0.4062	0.0046	0.226*
H22C	0.1133	0.3417	0.0429	0.226*
C25	0.0936 (15)	0.1639 (10)	0.1242 (7)	0.155 (4)
H25A	0.1470	0.2459	0.1736	0.232*
H25B	0.0624	0.0959	0.1521	0.232*
H25C	−0.0126	0.1758	0.0847	0.232*
C23	0.4459 (12)	0.1841 (8)	−0.0222 (5)	0.113 (3)
H23A	0.5272	0.1372	0.0065	0.169*
H23B	0.5130	0.2542	−0.0373	0.169*
H23C	0.3671	0.1237	−0.0792	0.169*

	U11	U22	U33	U12	U13	U23
Br1	0.0725 (4)	0.0449 (3)	0.0923 (5)	−0.0143 (3)	0.0195 (3)	0.0238 (3)
Br2	0.0604 (4)	0.0956 (5)	0.0726 (5)	0.0205 (3)	0.0054 (3)	0.0452 (4)
C1	0.045 (3)	0.026 (2)	0.051 (3)	−0.0006 (18)	0.012 (2)	0.0140 (18)
C2	0.047 (3)	0.035 (2)	0.056 (3)	0.0005 (19)	0.024 (2)	0.021 (2)
C3	0.067 (3)	0.035 (2)	0.049 (3)	0.005 (2)	0.021 (2)	0.019 (2)
C4	0.060 (3)	0.034 (2)	0.045 (3)	0.002 (2)	0.015 (2)	0.018 (2)
C5	0.070 (3)	0.028 (2)	0.050 (3)	0.007 (2)	0.021 (2)	0.0159 (19)
C6	0.049 (3)	0.039 (2)	0.054 (3)	0.013 (2)	0.017 (2)	0.023 (2)
C7	0.050 (3)	0.034 (2)	0.040 (3)	0.0032 (19)	0.011 (2)	0.0167 (19)
C8	0.047 (3)	0.041 (3)	0.053 (3)	0.009 (2)	0.020 (2)	0.014 (2)
C9	0.054 (3)	0.028 (2)	0.044 (3)	0.0075 (19)	0.020 (2)	0.0130 (18)
C10	0.068 (3)	0.031 (2)	0.045 (3)	0.008 (2)	0.024 (2)	0.0141 (19)
C11	0.111 (5)	0.039 (3)	0.066 (4)	0.019 (3)	0.037 (3)	0.027 (3)
C12	0.080 (4)	0.077 (4)	0.103 (5)	0.043 (4)	0.042 (4)	0.055 (4)
C13	0.061 (4)	0.079 (4)	0.080 (4)	0.027 (3)	0.028 (3)	0.040 (3)
C14	0.053 (3)	0.041 (3)	0.072 (4)	0.007 (2)	0.021 (3)	0.025 (2)
C15	0.045 (3)	0.031 (2)	0.040 (3)	0.0051 (18)	0.013 (2)	0.0095 (18)
C16	0.043 (3)	0.044 (3)	0.063 (3)	0.007 (2)	0.015 (2)	0.024 (2)
C17	0.050 (3)	0.064 (3)	0.064 (3)	−0.003 (3)	0.014 (3)	0.025 (3)
C18	0.075 (4)	0.046 (3)	0.055 (3)	−0.007 (3)	0.025 (3)	0.018 (2)
C19	0.076 (4)	0.039 (3)	0.043 (3)	0.008 (2)	0.018 (2)	0.019 (2)
C20	0.053 (3)	0.036 (2)	0.041 (3)	0.014 (2)	0.016 (2)	0.0135 (19)
N1	0.046 (2)	0.0310 (18)	0.057 (2)	0.0084 (16)	0.0239 (18)	0.0205 (17)
O1	0.050 (2)	0.078 (3)	0.096 (3)	0.019 (2)	0.033 (2)	0.039 (2)
C21	0.095 (5)	0.049 (3)	0.062 (4)	−0.017 (3)	0.001 (3)	0.021 (3)
C24	0.197 (9)	0.131 (6)	0.100 (5)	−0.054 (6)	0.005 (4)	0.034 (5)
C22	0.179 (9)	0.106 (6)	0.120 (7)	−0.064 (6)	−0.080 (6)	0.078 (5)
C25	0.197 (9)	0.131 (6)	0.100 (5)	−0.054 (6)	0.005 (4)	0.034 (5)
C23	0.160 (8)	0.107 (6)	0.041 (4)	−0.016 (5)	0.017 (4)	−0.004 (3)

Br1—C10	1.908 (5)	C12—H12	0.9300
Br2—C20	1.904 (5)	C13—C14	1.380 (7)
C1—N1	1.476 (5)	C13—H13	0.9300
C1—C9	1.507 (6)	C14—H14	0.9300
C1—C2	1.537 (7)	C15—C20	1.400 (6)
C1—H1	0.9800	C15—C16	1.402 (6)
C2—C8	1.521 (6)	C16—C17	1.379 (7)
C2—C3	1.542 (7)	C16—H16	0.9300
C2—H2	0.9800	C17—C18	1.390 (8)
C3—C4	1.534 (6)	C17—H17	0.9300
C3—H3A	0.9700	C18—C19	1.367 (7)
C3—H3B	0.9700	C18—H18	0.9300
C4—C5	1.528 (6)	C19—C20	1.381 (6)
C4—C21	1.574 (7)	C19—H19	0.9300
C4—H4	0.9800	N1—H1A	0.8600
C5—C6	1.538 (6)	C21—C24	1.537 (10)
C5—H5A	0.9700	C21—C22	1.565 (11)
C5—H5B	0.9700	C21—C23	1.567 (10)
C6—C8	1.483 (6)	C24—C25	1.553 (12)
C6—C7	1.531 (6)	C24—H24A	0.9700
C6—H6	0.9800	C24—H24B	0.9700
C7—N1	1.468 (6)	C22—H22A	0.9600
C7—C15	1.503 (6)	C22—H22B	0.9600
C7—H7	0.9800	C22—H22C	0.9600
C8—O1	1.220 (6)	C25—H25A	0.9600
C9—C14	1.364 (7)	C25—H25B	0.9600
C9—C10	1.406 (6)	C25—H25C	0.9600
C10—C11	1.385 (7)	C23—H23A	0.9600
C11—C12	1.376 (8)	C23—H23B	0.9600
C11—H11	0.9300	C23—H23C	0.9600
C12—C13	1.401 (8)
N1—C1—C9	108.6 (4)	C14—C13—C12	119.0 (6)
N1—C1—C2	110.2 (3)	C14—C13—H13	120.5
C9—C1—C2	113.0 (4)	C12—C13—H13	120.5
N1—C1—H1	108.3	C9—C14—C13	123.5 (5)
C9—C1—H1	108.3	C9—C14—H14	118.2
C2—C1—H1	108.3	C13—C14—H14	118.2
C8—C2—C1	107.1 (4)	C20—C15—C16	115.7 (4)
C8—C2—C3	107.6 (4)	C20—C15—C7	123.0 (4)
C1—C2—C3	116.3 (4)	C16—C15—C7	121.3 (4)
C8—C2—H2	108.5	C17—C16—C15	122.0 (4)
C1—C2—H2	108.5	C17—C16—H16	119.0
C3—C2—H2	108.5	C15—C16—H16	119.0
C4—C3—C2	115.2 (4)	C16—C17—C18	120.0 (5)
C4—C3—H3A	108.5	C16—C17—H17	120.0
C2—C3—H3A	108.5	C18—C17—H17	120.0
C4—C3—H3B	108.5	C19—C18—C17	119.7 (5)
C2—C3—H3B	108.5	C19—C18—H18	120.1
H3A—C3—H3B	107.5	C17—C18—H18	120.1
C5—C4—C3	111.0 (4)	C18—C19—C20	119.8 (5)
C5—C4—C21	114.0 (4)	C18—C19—H19	120.1
C3—C4—C21	112.0 (4)	C20—C19—H19	120.1
C5—C4—H4	106.4	C19—C20—C15	122.7 (5)
C3—C4—H4	106.4	C19—C20—Br2	116.5 (3)
C21—C4—H4	106.4	C15—C20—Br2	120.8 (3)
C4—C5—C6	116.3 (4)	C7—N1—C1	114.5 (4)
C4—C5—H5A	108.2	C7—N1—H1A	122.7
C6—C5—H5A	108.2	C1—N1—H1A	122.7
C4—C5—H5B	108.2	C24—C21—C22	110.5 (7)
C6—C5—H5B	108.2	C24—C21—C23	103.6 (6)
H5A—C5—H5B	107.4	C22—C21—C23	111.4 (7)
C8—C6—C7	108.2 (4)	C24—C21—C4	109.9 (5)
C8—C6—C5	107.5 (4)	C22—C21—C4	110.9 (5)
C7—C6—C5	114.9 (4)	C23—C21—C4	110.3 (5)
C8—C6—H6	108.7	C21—C24—C25	110.3 (8)
C7—C6—H6	108.7	C21—C24—H24A	109.6
C5—C6—H6	108.7	C25—C24—H24A	109.6
N1—C7—C15	109.9 (4)	C21—C24—H24B	109.6
N1—C7—C6	111.0 (3)	C25—C24—H24B	109.6
C15—C7—C6	112.2 (3)	H24A—C24—H24B	108.1
N1—C7—H7	107.9	C21—C22—H22A	109.5
C15—C7—H7	107.9	C21—C22—H22B	109.5
C6—C7—H7	107.9	H22A—C22—H22B	109.5
O1—C8—C6	125.0 (4)	C21—C22—H22C	109.5
O1—C8—C2	123.3 (4)	H22A—C22—H22C	109.5
C6—C8—C2	111.7 (4)	H22B—C22—H22C	109.5
C14—C9—C10	116.3 (4)	C24—C25—H25A	109.5
C14—C9—C1	122.2 (4)	C24—C25—H25B	109.5
C10—C9—C1	121.5 (4)	H25A—C25—H25B	109.5
C11—C10—C9	122.0 (5)	C24—C25—H25C	109.5
C11—C10—Br1	116.8 (4)	H25A—C25—H25C	109.5
C9—C10—Br1	121.2 (4)	H25B—C25—H25C	109.5
C12—C11—C10	119.8 (5)	C21—C23—H23A	109.5
C12—C11—H11	120.1	C21—C23—H23B	109.5
C10—C11—H11	120.1	H23A—C23—H23B	109.5
C11—C12—C13	119.4 (5)	C21—C23—H23C	109.5
C11—C12—H12	120.3	H23A—C23—H23C	109.5
C13—C12—H12	120.3	H23B—C23—H23C	109.5
N1—C1—C2—C8	−56.2 (5)	C10—C11—C12—C13	−1.7 (9)
C9—C1—C2—C8	−178.0 (4)	C11—C12—C13—C14	3.2 (9)
N1—C1—C2—C3	64.1 (5)	C10—C9—C14—C13	−0.1 (8)
C9—C1—C2—C3	−57.7 (5)	C1—C9—C14—C13	179.5 (5)
C8—C2—C3—C4	52.9 (5)	C12—C13—C14—C9	−2.4 (9)
C1—C2—C3—C4	−67.2 (5)	N1—C7—C15—C20	−156.6 (4)
C2—C3—C4—C5	−43.5 (5)	C6—C7—C15—C20	79.4 (5)
C2—C3—C4—C21	−172.2 (4)	N1—C7—C15—C16	25.0 (6)
C3—C4—C5—C6	43.8 (5)	C6—C7—C15—C16	−99.0 (5)
C21—C4—C5—C6	171.4 (4)	C20—C15—C16—C17	−2.7 (7)
C4—C5—C6—C8	−53.5 (5)	C7—C15—C16—C17	175.8 (5)
C4—C5—C6—C7	67.0 (5)	C15—C16—C17—C18	1.3 (8)
C8—C6—C7—N1	55.2 (5)	C16—C17—C18—C19	0.3 (8)
C5—C6—C7—N1	−64.8 (5)	C17—C18—C19—C20	−0.4 (8)
C8—C6—C7—C15	178.6 (4)	C18—C19—C20—C15	−1.1 (7)
C5—C6—C7—C15	58.6 (5)	C18—C19—C20—Br2	179.1 (4)
C7—C6—C8—O1	118.8 (5)	C16—C15—C20—C19	2.6 (6)
C5—C6—C8—O1	−116.6 (5)	C7—C15—C20—C19	−175.9 (4)
C7—C6—C8—C2	−61.2 (5)	C16—C15—C20—Br2	−177.6 (3)
C5—C6—C8—C2	63.4 (5)	C7—C15—C20—Br2	3.9 (6)
C1—C2—C8—O1	−118.1 (5)	C15—C7—N1—C1	−178.9 (3)
C3—C2—C8—O1	116.2 (5)	C6—C7—N1—C1	−54.2 (5)
C1—C2—C8—C6	61.9 (5)	C9—C1—N1—C7	179.5 (3)
C3—C2—C8—C6	−63.8 (5)	C2—C1—N1—C7	55.1 (5)
N1—C1—C9—C14	−28.3 (6)	C5—C4—C21—C24	48.8 (8)
C2—C1—C9—C14	94.4 (5)	C3—C4—C21—C24	175.8 (6)
N1—C1—C9—C10	151.3 (4)	C5—C4—C21—C22	171.4 (6)
C2—C1—C9—C10	−86.0 (5)	C3—C4—C21—C22	−61.6 (7)
C14—C9—C10—C11	1.8 (7)	C5—C4—C21—C23	−64.8 (6)
C1—C9—C10—C11	−177.9 (4)	C3—C4—C21—C23	62.3 (6)
C14—C9—C10—Br1	−179.2 (4)	C22—C21—C24—C25	−54.6 (10)
C1—C9—C10—Br1	1.1 (6)	C23—C21—C24—C25	−174.0 (8)
C9—C10—C11—C12	−0.9 (8)	C4—C21—C24—C25	68.2 (10)
Br1—C10—C11—C12	−179.9 (5)