(2S,4S)-2-[(S,E)-2-Bromo-1-nitro-methyl-3-phenyl-all-yl]-4-methyl-cyclo-hexa-none.

The crystal structure of the title compoud, C(17)H(20)BrNO(3), contains three chiral centers, which all exhibit an S configuration. The C=C double bond has an E conformation. The cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by weak N-O⋯Br inter-actions [O⋯Br = 3.136 (4) Å].

Related literature

For related compounds, see: Li et al. (2009 ▶); Wu et al. (2011 ▶). For the asymmetric Michael reaction, which allows for the formation of three contiguous asymmetric centers, see: Agarwal & Peddinti (2011 ▶); Lu et al. (2010 ▶); Luo et al. (2007 ▶).

Experimental

Crystal data

C17H20BrNO3

M = 366.25

Orthorhombic,

a = 7.0942 (5) Å

b = 13.7920 (11) Å

c = 17.3108 (13) Å

V = 1693.7 (2) Å3

Z = 4

Mo Kα radiation

μ = 2.44 mm−1

T = 296 K

0.40 × 0.38 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.377, T max = 0.481

13310 measured reflections

3829 independent reflections

1967 reflections with I > 2σ(I)

R int = 0.092

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 0.91

3829 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.35 e Å−3

Absolute structure: Flack (1983 ▶), 1625 Friedel pairs

Flack parameter: −0.019 (14)

Data collection: PROCESS-AUTO (Rigaku, 2006 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812013098/bh2424sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812013098/bh2424Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812013098/bh2424Isup3.cml

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

C17H20BrNO3	F(000) = 752
Mr = 366.25	Dx = 1.436 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8068 reflections
a = 7.0942 (5) Å	θ = 3.1–27.4°
b = 13.7920 (11) Å	µ = 2.44 mm−1
c = 17.3108 (13) Å	T = 296 K
V = 1693.7 (2) Å3	Chunk, colourless
Z = 4	0.40 × 0.38 × 0.30 mm

Rigaku R-AXIS RAPID/ZJUG diffractometer	3829 independent reflections
Radiation source: rotating anode	1967 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.092
Detector resolution: 10.00 pixels mm-1	θmax = 27.4°, θmin = 3.1°
ω scans	h = −9→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
Tmin = 0.377, Tmax = 0.481	l = −22→21
13310 measured reflections

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)] = 0.040	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.030P)2] where P = (Fo2 + 2Fc2)/3
S = 0.91	(Δ/σ)max = 0.001
3829 reflections	Δρmax = 0.29 e Å−3
200 parameters	Δρmin = −0.35 e Å−3
0 restraints	Absolute structure: Flack (1983), 1625 Friedel pairs
0 constraints	Flack parameter: −0.019 (14)
Primary atom site location: structure-invariant direct methods

	x	y	z	Uiso*/Ueq
Br1	1.02011 (8)	0.36551 (3)	0.51179 (3)	0.0761 (2)
O1	0.4791 (5)	0.6330 (2)	0.46539 (18)	0.0755 (8)
O2	0.5698 (8)	0.3042 (3)	0.6070 (2)	0.1185 (17)
O3	0.4316 (6)	0.4334 (4)	0.6423 (2)	0.1077 (15)
N1	0.5198 (7)	0.3865 (3)	0.5965 (2)	0.0757 (12)
C2	0.7862 (6)	0.5611 (3)	0.4626 (2)	0.0501 (11)
H2	0.8173	0.5116	0.4240	0.060*
C1	0.7353 (6)	0.5087 (3)	0.5385 (2)	0.0483 (11)
H1	0.6865	0.5576	0.5744	0.058*
C3	0.6255 (7)	0.6214 (3)	0.4309 (2)	0.0579 (12)
C4	0.6690 (7)	0.6733 (4)	0.3565 (3)	0.0762 (15)
H4A	0.5633	0.7141	0.3422	0.091*
H4B	0.6880	0.6261	0.3156	0.091*
C5	0.8469 (8)	0.7357 (4)	0.3653 (3)	0.0817 (17)
H5A	0.8806	0.7624	0.3154	0.098*
H5B	0.8197	0.7894	0.3997	0.098*
C6	1.0146 (7)	0.6786 (3)	0.3972 (2)	0.0627 (11)
H6	1.1128	0.7259	0.4101	0.075*
C7	0.9604 (6)	0.6279 (3)	0.4720 (2)	0.0565 (10)
H7A	0.9335	0.6764	0.5111	0.068*
H7B	1.0663	0.5896	0.4899	0.068*
C8	1.0995 (8)	0.6087 (4)	0.3388 (3)	0.0883 (18)
H8A	1.2033	0.5748	0.3620	0.132*
H8B	1.1435	0.6443	0.2947	0.132*
H8C	1.0055	0.5629	0.3228	0.132*
C9	0.9023 (7)	0.4616 (3)	0.5761 (2)	0.0563 (12)
C10	0.9783 (7)	0.4757 (3)	0.6453 (2)	0.0599 (11)
H10	1.0773	0.4343	0.6576	0.072*
C11	0.9294 (7)	0.5474 (3)	0.7059 (2)	0.0537 (12)
C12	0.7487 (7)	0.5782 (4)	0.7244 (2)	0.0666 (14)
H12	0.6465	0.5530	0.6974	0.080*
C13	0.7176 (8)	0.6451 (4)	0.7817 (3)	0.0798 (16)
H13	0.5954	0.6654	0.7925	0.096*
C14	0.8649 (10)	0.6819 (4)	0.8232 (3)	0.0842 (18)
H14	0.8432	0.7277	0.8616	0.101*
C15	1.0436 (9)	0.6515 (4)	0.8081 (3)	0.0895 (18)
H15	1.1443	0.6762	0.8363	0.107*
C16	1.0753 (7)	0.5830 (4)	0.7500 (2)	0.0720 (14)
H16	1.1973	0.5611	0.7410	0.086*
C17	0.5758 (6)	0.4353 (3)	0.5233 (2)	0.0625 (12)
H17A	0.4679	0.4686	0.5014	0.075*
H17B	0.6182	0.3871	0.4863	0.075*

	U11	U22	U33	U12	U13	U23
Br1	0.1030 (4)	0.0633 (3)	0.0619 (3)	0.0246 (3)	−0.0012 (3)	−0.0079 (2)
O1	0.067 (2)	0.076 (2)	0.083 (2)	0.016 (2)	0.0017 (18)	−0.0001 (17)
O2	0.175 (5)	0.079 (3)	0.101 (3)	−0.029 (3)	0.004 (3)	0.017 (2)
O3	0.105 (3)	0.132 (4)	0.086 (2)	−0.027 (3)	0.031 (2)	−0.021 (3)
N1	0.083 (3)	0.078 (3)	0.066 (2)	−0.029 (3)	0.000 (3)	−0.005 (2)
C2	0.060 (3)	0.041 (3)	0.049 (2)	−0.001 (2)	−0.001 (2)	−0.0039 (19)
C1	0.052 (3)	0.044 (3)	0.049 (2)	−0.002 (2)	−0.006 (2)	−0.0027 (19)
C3	0.057 (3)	0.058 (3)	0.059 (3)	−0.003 (3)	−0.014 (2)	−0.002 (2)
C4	0.084 (4)	0.078 (4)	0.067 (3)	0.004 (3)	−0.016 (3)	0.017 (3)
C5	0.089 (4)	0.077 (4)	0.079 (3)	−0.003 (3)	−0.001 (3)	0.022 (3)
C6	0.070 (3)	0.059 (3)	0.059 (2)	−0.010 (3)	0.002 (3)	0.003 (2)
C7	0.054 (3)	0.060 (3)	0.056 (2)	−0.004 (2)	0.002 (2)	−0.002 (2)
C8	0.092 (4)	0.105 (5)	0.068 (3)	−0.014 (3)	0.010 (3)	0.001 (3)
C9	0.066 (3)	0.052 (3)	0.051 (2)	−0.007 (2)	0.002 (2)	−0.001 (2)
C10	0.067 (3)	0.056 (3)	0.056 (2)	0.012 (3)	−0.005 (3)	0.0023 (19)
C11	0.065 (3)	0.054 (3)	0.042 (2)	0.001 (2)	−0.010 (2)	0.0020 (19)
C12	0.066 (4)	0.088 (4)	0.047 (3)	0.002 (3)	−0.003 (2)	−0.008 (2)
C13	0.103 (4)	0.084 (4)	0.052 (3)	0.017 (4)	−0.001 (3)	−0.011 (3)
C14	0.140 (6)	0.061 (4)	0.052 (3)	0.000 (4)	−0.001 (4)	−0.008 (3)
C15	0.116 (6)	0.089 (4)	0.064 (3)	−0.026 (4)	−0.016 (3)	−0.014 (3)
C16	0.073 (4)	0.082 (4)	0.061 (3)	−0.004 (3)	−0.005 (3)	0.003 (3)
C17	0.073 (3)	0.063 (3)	0.051 (2)	−0.020 (2)	−0.005 (2)	0.002 (2)

Br1—C9	1.923 (4)	C7—H7A	0.9700
O1—C3	1.208 (5)	C7—H7B	0.9700
O2—N1	1.203 (5)	C8—H8A	0.9600
O3—N1	1.199 (5)	C8—H8B	0.9600
N1—C17	1.490 (5)	C8—H8C	0.9600
C2—C3	1.514 (6)	C9—C10	1.328 (5)
C2—C1	1.542 (5)	C10—C11	1.483 (6)
C2—C7	1.551 (5)	C10—H10	0.9300
C2—H2	0.9800	C11—C16	1.377 (6)
C1—C9	1.500 (6)	C11—C12	1.387 (6)
C1—C17	1.541 (6)	C12—C13	1.374 (7)
C1—H1	0.9800	C12—H12	0.9300
C3—C4	1.506 (6)	C13—C14	1.365 (8)
C4—C5	1.535 (7)	C13—H13	0.9300
C4—H4A	0.9700	C14—C15	1.361 (8)
C4—H4B	0.9700	C14—H14	0.9300
C5—C6	1.530 (6)	C15—C16	1.397 (7)
C5—H5A	0.9700	C15—H15	0.9300
C5—H5B	0.9700	C16—H16	0.9300
C6—C8	1.521 (6)	C17—H17A	0.9700
C6—C7	1.520 (5)	C17—H17B	0.9700
C6—H6	0.9800
O3—N1—O2	124.3 (5)	C6—C7—H7B	109.1
O3—N1—C17	117.3 (5)	C2—C7—H7B	109.1
O2—N1—C17	118.4 (5)	H7A—C7—H7B	107.8
C3—C2—C1	112.9 (4)	C6—C8—H8A	109.5
C3—C2—C7	108.1 (3)	C6—C8—H8B	109.5
C1—C2—C7	112.0 (3)	H8A—C8—H8B	109.5
C3—C2—H2	107.8	C6—C8—H8C	109.5
C1—C2—H2	107.8	H8A—C8—H8C	109.5
C7—C2—H2	107.8	H8B—C8—H8C	109.5
C9—C1—C17	111.7 (4)	C10—C9—C1	130.5 (4)
C9—C1—C2	112.9 (3)	C10—C9—Br1	116.5 (4)
C17—C1—C2	109.5 (3)	C1—C9—Br1	113.0 (3)
C9—C1—H1	107.5	C9—C10—C11	129.8 (4)
C17—C1—H1	107.5	C9—C10—H10	115.1
C2—C1—H1	107.5	C11—C10—H10	115.1
O1—C3—C4	122.4 (4)	C16—C11—C12	117.2 (4)
O1—C3—C2	122.7 (4)	C16—C11—C10	117.0 (4)
C4—C3—C2	114.6 (4)	C12—C11—C10	125.7 (4)
C3—C4—C5	110.4 (4)	C13—C12—C11	121.3 (5)
C3—C4—H4A	109.6	C13—C12—H12	119.3
C5—C4—H4A	109.6	C11—C12—H12	119.3
C3—C4—H4B	109.6	C14—C13—C12	120.5 (5)
C5—C4—H4B	109.6	C14—C13—H13	119.8
H4A—C4—H4B	108.1	C12—C13—H13	119.8
C6—C5—C4	112.7 (4)	C15—C14—C13	119.8 (5)
C6—C5—H5A	109.0	C15—C14—H14	120.1
C4—C5—H5A	109.0	C13—C14—H14	120.1
C6—C5—H5B	109.0	C14—C15—C16	119.8 (5)
C4—C5—H5B	109.0	C14—C15—H15	120.1
H5A—C5—H5B	107.8	C16—C15—H15	120.1
C8—C6—C7	112.1 (4)	C11—C16—C15	121.3 (5)
C8—C6—C5	113.2 (4)	C11—C16—H16	119.4
C7—C6—C5	110.3 (4)	C15—C16—H16	119.4
C8—C6—H6	107.0	N1—C17—C1	110.3 (3)
C7—C6—H6	107.0	N1—C17—H17A	109.6
C5—C6—H6	107.0	C1—C17—H17A	109.6
C6—C7—C2	112.7 (3)	N1—C17—H17B	109.6
C6—C7—H7A	109.1	C1—C17—H17B	109.6
C2—C7—H7A	109.1	H17A—C17—H17B	108.1
C3—C2—C1—C9	−171.2 (3)	C17—C1—C9—Br1	63.8 (4)
C7—C2—C1—C9	−48.7 (5)	C2—C1—C9—Br1	−60.0 (4)
C3—C2—C1—C17	63.8 (5)	C1—C9—C10—C11	−4.4 (8)
C7—C2—C1—C17	−173.8 (3)	Br1—C9—C10—C11	175.8 (4)
C1—C2—C3—O1	5.7 (6)	C9—C10—C11—C16	−146.0 (5)
C7—C2—C3—O1	−118.9 (5)	C9—C10—C11—C12	37.3 (8)
C1—C2—C3—C4	−179.6 (4)	C16—C11—C12—C13	3.2 (7)
C7—C2—C3—C4	55.8 (5)	C10—C11—C12—C13	179.9 (5)
O1—C3—C4—C5	120.0 (5)	C11—C12—C13—C14	−1.1 (9)
C2—C3—C4—C5	−54.7 (6)	C12—C13—C14—C15	−0.7 (9)
C3—C4—C5—C6	52.3 (6)	C13—C14—C15—C16	0.3 (9)
C4—C5—C6—C8	73.0 (5)	C12—C11—C16—C15	−3.6 (7)
C4—C5—C6—C7	−53.5 (5)	C10—C11—C16—C15	179.4 (4)
C8—C6—C7—C2	−71.2 (5)	C14—C15—C16—C11	1.9 (8)
C5—C6—C7—C2	55.9 (5)	O3—N1—C17—C1	73.0 (5)
C3—C2—C7—C6	−56.0 (4)	O2—N1—C17—C1	−104.9 (5)
C1—C2—C7—C6	178.9 (4)	C9—C1—C17—N1	56.4 (5)
C17—C1—C9—C10	−115.9 (5)	C2—C1—C17—N1	−177.9 (4)
C2—C1—C9—C10	120.2 (5)