(2S,4R)-2-[(1R)-1-(4-Bromo-phen-yl)-2-nitro-eth-yl]-4-ethyl-cyclo-hexa-none.

The crystal structure of the title compound, C(16)H(20)BrNO(3), contains three chiral centers in the configuration 1R,2S,6R. The cyclo-hexane ring is in a chair conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, forming chains along the a-axis direction.

Related literature

For related compounds, see: Hayashi et al. (2005 ▶); Li et al. (2009 ▶); Xia et al. (2009 ▶); Wu et al. (2011 ▶). For asymmetric Michael addition reactions, see: Luo et al. (2007 ▶). For enanti­oselective organocatalytic Michael additions, see: Peelen et al. (2005 ▶); Ma et al. (2008 ▶).

Experimental

Crystal data

C16H20BrNO3

M = 354.24

Monoclinic,

a = 5.6434 (4) Å

b = 9.2179 (6) Å

c = 16.5472 (9) Å

β = 101.782 (3)°

V = 842.65 (9) Å3

Z = 2

Mo Kα radiation

μ = 2.45 mm−1

T = 296 K

0.52 × 0.31 × 0.18 mm

Data collection

Rigaku R-AXIS RAPID/ZJUG diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.279, T max = 0.644

7234 measured reflections

3277 independent reflections

1619 reflections with I > 2σ(I)

R int = 0.071

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.175

S = 1.00

3277 reflections

191 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.29 e Å−3

Absolute structure: Flack (1983 ▶), 1259 Friedel pairs

Flack parameter: 0.03 (2)

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, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001426/zq2194sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001426/zq2194Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813001426/zq2194Isup3.cml

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

C16H20BrNO3	F(000) = 364
Mr = 354.24	Dx = 1.396 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4682 reflections
a = 5.6434 (4) Å	θ = 3.4–27.4°
b = 9.2179 (6) Å	µ = 2.45 mm−1
c = 16.5472 (9) Å	T = 296 K
β = 101.782 (3)°	Platelet, colourless
V = 842.65 (9) Å3	0.52 × 0.31 × 0.18 mm
Z = 2

Rigaku R-AXIS RAPID/ZJUG diffractometer	3277 independent reflections
Radiation source: rotating anode	1619 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.071
Detector resolution: 10.00 pixels mm-1	θmax = 26.0°, θmin = 3.4°
ω scans	h = −6→6
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −11→11
Tmin = 0.279, Tmax = 0.644	l = −20→20
7234 measured reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.056	w = 1/[σ2(Fo2) + (0.0605P)2 + 0.3P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.175	(Δ/σ)max < 0.001
S = 1.00	Δρmax = 0.35 e Å−3
3277 reflections	Δρmin = −0.29 e Å−3
191 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraint	Extinction coefficient: 0.072 (8)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1259 Friedel pairs
Secondary atom site location: difference Fourier map	Flack parameter: 0.03 (2)

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 taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used 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 and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 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	0.2312 (11)	0.2884 (7)	0.1770 (4)	0.0563 (15)
H1	0.0766	0.3379	0.1754	0.068*
C2	0.4174 (11)	0.4066 (6)	0.1660 (4)	0.0541 (15)
H2	0.5499	0.3592	0.1461	0.065*
C3	0.3093 (14)	0.5225 (7)	0.1030 (4)	0.0712 (19)
C4	0.4813 (15)	0.6373 (10)	0.0880 (5)	0.091 (3)
H4A	0.3957	0.7096	0.0504	0.109*
H4B	0.6060	0.5948	0.0629	0.109*
C5	0.5974 (14)	0.7093 (9)	0.1702 (5)	0.090 (2)
H5A	0.7190	0.7778	0.1605	0.108*
H5B	0.4742	0.7634	0.1905	0.108*
C6	0.7146 (11)	0.6025 (7)	0.2361 (5)	0.0672 (18)
H6	0.8446	0.5533	0.2156	0.081*
C7	0.5264 (10)	0.4859 (8)	0.2467 (3)	0.0582 (14)
H7A	0.6031	0.4153	0.2872	0.070*
H7B	0.3969	0.5317	0.2679	0.070*
C8	0.8263 (14)	0.6704 (9)	0.3179 (5)	0.089 (2)
H8A	0.8867	0.5934	0.3565	0.107*
H8B	0.6999	0.7206	0.3387	0.107*
C9	1.0317 (16)	0.7769 (10)	0.3167 (7)	0.110 (3)
H9A	1.0904	0.8137	0.3714	0.165*
H9B	0.9736	0.8558	0.2802	0.165*
H9C	1.1607	0.7282	0.2978	0.165*
C10	0.2948 (10)	0.2114 (7)	0.2592 (4)	0.0522 (14)
C11	0.4955 (12)	0.1193 (7)	0.2768 (4)	0.0646 (17)
H11	0.5875	0.1042	0.2369	0.078*
C12	0.5606 (13)	0.0500 (7)	0.3524 (5)	0.075 (2)
H12	0.6965	−0.0094	0.3637	0.090*
C13	0.4189 (15)	0.0708 (8)	0.4112 (5)	0.076 (2)
C14	0.2187 (14)	0.1583 (8)	0.3947 (4)	0.0708 (19)
H14	0.1244	0.1714	0.4341	0.085*
C15	0.1579 (11)	0.2267 (8)	0.3194 (4)	0.0622 (17)
H15	0.0206	0.2851	0.3085	0.075*
C16	0.1937 (11)	0.1852 (7)	0.1032 (4)	0.0616 (17)
H16A	0.1394	0.2399	0.0527	0.074*
H16B	0.3464	0.1395	0.1001	0.074*
N1	0.0135 (12)	0.0724 (7)	0.1101 (4)	0.0700 (16)
O1	0.0953 (10)	0.5240 (6)	0.0704 (3)	0.0925 (19)
O2	0.0723 (11)	−0.0541 (7)	0.1111 (4)	0.1028 (18)
O3	−0.1912 (9)	0.1117 (7)	0.1163 (3)	0.0939 (17)
Br1	0.5073 (2)	−0.02467 (17)	0.51442 (5)	0.1269 (6)

	U11	U22	U33	U12	U13	U23
C1	0.058 (3)	0.059 (3)	0.054 (4)	−0.002 (3)	0.015 (3)	−0.004 (3)
C2	0.053 (3)	0.055 (3)	0.056 (3)	−0.005 (3)	0.015 (3)	0.006 (3)
C3	0.089 (5)	0.074 (5)	0.053 (4)	−0.003 (4)	0.019 (3)	0.010 (3)
C4	0.096 (5)	0.099 (6)	0.074 (5)	−0.021 (5)	0.007 (4)	0.028 (4)
C5	0.084 (5)	0.071 (5)	0.120 (7)	−0.004 (4)	0.028 (5)	0.035 (5)
C6	0.058 (4)	0.052 (4)	0.091 (5)	−0.004 (3)	0.012 (4)	−0.001 (4)
C7	0.063 (3)	0.050 (3)	0.059 (3)	0.002 (3)	0.008 (3)	−0.005 (4)
C8	0.084 (5)	0.076 (5)	0.105 (6)	−0.013 (4)	0.013 (4)	−0.015 (4)
C9	0.087 (5)	0.092 (6)	0.153 (10)	−0.022 (5)	0.030 (6)	−0.035 (6)
C10	0.050 (3)	0.050 (3)	0.056 (4)	0.002 (3)	0.009 (3)	0.005 (3)
C11	0.072 (4)	0.067 (4)	0.059 (4)	0.004 (4)	0.023 (3)	0.010 (3)
C12	0.069 (4)	0.061 (4)	0.089 (5)	0.005 (3)	0.000 (4)	−0.002 (4)
C13	0.094 (5)	0.069 (4)	0.063 (4)	−0.006 (4)	0.011 (4)	−0.015 (4)
C14	0.085 (5)	0.083 (5)	0.047 (4)	0.001 (4)	0.020 (3)	−0.003 (3)
C15	0.062 (4)	0.066 (4)	0.062 (4)	0.001 (4)	0.019 (3)	0.002 (3)
C16	0.060 (3)	0.074 (5)	0.051 (3)	−0.011 (3)	0.012 (3)	−0.008 (4)
N1	0.077 (4)	0.078 (5)	0.053 (3)	−0.015 (4)	0.009 (3)	−0.001 (3)
O1	0.081 (3)	0.111 (5)	0.077 (3)	0.000 (3)	−0.003 (3)	0.031 (3)
O2	0.107 (4)	0.067 (4)	0.128 (5)	−0.012 (3)	0.007 (3)	0.016 (3)
O3	0.063 (3)	0.127 (5)	0.097 (4)	−0.028 (3)	0.030 (3)	−0.031 (3)
Br1	0.1788 (11)	0.1258 (9)	0.0677 (6)	0.0169 (8)	0.0050 (5)	0.0258 (7)

C1—C10	1.511 (8)	C8—H8A	0.9700
C1—C16	1.528 (8)	C8—H8B	0.9700
C1—C2	1.550 (8)	C9—H9A	0.9600
C1—H1	0.9800	C9—H9B	0.9600
C2—C3	1.530 (8)	C9—H9C	0.9600
C2—C7	1.535 (8)	C10—C15	1.387 (8)
C2—H2	0.9800	C10—C11	1.398 (8)
C3—O1	1.218 (8)	C11—C12	1.386 (9)
C3—C4	1.490 (10)	C11—H11	0.9300
C4—C5	1.536 (12)	C12—C13	1.392 (11)
C4—H4A	0.9700	C12—H12	0.9300
C4—H4B	0.9700	C13—C14	1.370 (10)
C5—C6	1.517 (10)	C13—Br1	1.896 (8)
C5—H5A	0.9700	C14—C15	1.376 (9)
C5—H5B	0.9700	C14—H14	0.9300
C6—C8	1.506 (10)	C15—H15	0.9300
C6—C7	1.546 (9)	C16—N1	1.475 (9)
C6—H6	0.9800	C16—H16A	0.9700
C7—H7A	0.9700	C16—H16B	0.9700
C7—H7B	0.9700	N1—O2	1.212 (9)
C8—C9	1.522 (11)	N1—O3	1.235 (7)
C10—C1—C16	113.3 (5)	C6—C8—C9	115.9 (8)
C10—C1—C2	113.2 (5)	C6—C8—H8A	108.3
C16—C1—C2	109.3 (5)	C9—C8—H8A	108.3
C10—C1—H1	106.9	C6—C8—H8B	108.3
C16—C1—H1	106.9	C9—C8—H8B	108.3
C2—C1—H1	106.9	H8A—C8—H8B	107.4
C3—C2—C7	107.1 (5)	C8—C9—H9A	109.5
C3—C2—C1	112.7 (5)	C8—C9—H9B	109.5
C7—C2—C1	113.2 (5)	H9A—C9—H9B	109.5
C3—C2—H2	107.9	C8—C9—H9C	109.5
C7—C2—H2	107.9	H9A—C9—H9C	109.5
C1—C2—H2	107.9	H9B—C9—H9C	109.5
O1—C3—C4	122.6 (6)	C15—C10—C11	117.3 (6)
O1—C3—C2	122.0 (6)	C15—C10—C1	122.3 (5)
C4—C3—C2	115.3 (6)	C11—C10—C1	120.4 (5)
C3—C4—C5	109.5 (6)	C12—C11—C10	121.5 (6)
C3—C4—H4A	109.8	C12—C11—H11	119.2
C5—C4—H4A	109.8	C10—C11—H11	119.2
C3—C4—H4B	109.8	C11—C12—C13	118.9 (7)
C5—C4—H4B	109.8	C11—C12—H12	120.6
H4A—C4—H4B	108.2	C13—C12—H12	120.6
C6—C5—C4	113.7 (7)	C14—C13—C12	120.7 (7)
C6—C5—H5A	108.8	C14—C13—Br1	120.5 (6)
C4—C5—H5A	108.8	C12—C13—Br1	118.8 (6)
C6—C5—H5B	108.8	C15—C14—C13	119.6 (7)
C4—C5—H5B	108.8	C15—C14—H14	120.2
H5A—C5—H5B	107.7	C13—C14—H14	120.2
C8—C6—C5	114.6 (6)	C14—C15—C10	122.1 (6)
C8—C6—C7	111.0 (6)	C14—C15—H15	119.0
C5—C6—C7	108.9 (5)	C10—C15—H15	119.0
C8—C6—H6	107.3	N1—C16—C1	111.2 (5)
C5—C6—H6	107.3	N1—C16—H16A	109.4
C7—C6—H6	107.3	C1—C16—H16A	109.4
C2—C7—C6	113.3 (5)	N1—C16—H16B	109.4
C2—C7—H7A	108.9	C1—C16—H16B	109.4
C6—C7—H7A	108.9	H16A—C16—H16B	108.0
C2—C7—H7B	108.9	O2—N1—O3	122.6 (7)
C6—C7—H7B	108.9	O2—N1—C16	119.2 (7)
H7A—C7—H7B	107.7	O3—N1—C16	118.1 (6)
C10—C1—C2—C3	−156.6 (5)	C16—C1—C10—C15	−122.7 (7)
C16—C1—C2—C3	76.1 (6)	C2—C1—C10—C15	112.1 (7)
C10—C1—C2—C7	−34.9 (7)	C16—C1—C10—C11	56.5 (8)
C16—C1—C2—C7	−162.2 (5)	C2—C1—C10—C11	−68.7 (8)
C7—C2—C3—O1	−120.3 (7)	C15—C10—C11—C12	−2.2 (9)
C1—C2—C3—O1	4.8 (9)	C1—C10—C11—C12	178.6 (6)
C7—C2—C3—C4	56.5 (8)	C10—C11—C12—C13	1.3 (10)
C1—C2—C3—C4	−178.4 (6)	C11—C12—C13—C14	0.0 (11)
O1—C3—C4—C5	121.3 (8)	C11—C12—C13—Br1	179.8 (5)
C2—C3—C4—C5	−55.4 (9)	C12—C13—C14—C15	−0.3 (11)
C3—C4—C5—C6	53.7 (9)	Br1—C13—C14—C15	179.9 (6)
C4—C5—C6—C8	−179.0 (6)	C13—C14—C15—C10	−0.7 (11)
C4—C5—C6—C7	−54.0 (8)	C11—C10—C15—C14	1.9 (10)
C3—C2—C7—C6	−56.0 (7)	C1—C10—C15—C14	−178.9 (6)
C1—C2—C7—C6	179.2 (5)	C10—C1—C16—N1	54.0 (7)
C8—C6—C7—C2	−176.6 (5)	C2—C1—C16—N1	−178.8 (5)
C5—C6—C7—C2	56.3 (8)	C1—C16—N1—O2	−120.9 (8)
C5—C6—C8—C9	−61.7 (9)	C1—C16—N1—O3	57.6 (7)
C7—C6—C8—C9	174.4 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O3i	0.93	2.56	3.478 (9)	169
C16—H16B···O3i	0.97	2.58	3.500 (8)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O3i	0.93	2.56	3.478 (9)	169
C16—H16B⋯O3i	0.97	2.58	3.500 (8)	158

Symmetry code: (i) .