trans-2-(2-Nitro-1-phenyl-eth-yl)cyclo-hexa-none.

In the title compound, C(14)H(17)NO(3), the plane of the phenyl ring and the least-squares plane of the cyclo-hexyl moiety enclose an angle of 89.14 (6)°. The cyclohexyl ring adopts a chair conformation. In the crystal, the molecules are linked by weak C-H⋯O bonds, with each of the nitro-O atoms accepting two such interactions.

Related literature

For the history and synthesis of nitro­alkenes, see: Tsogoeva et al. (2007 ▶); Sulzer-Mosse & Alexakis (2007 ▶); Mukherjee et al. (2007 ▶); Kempf et al. (2003 ▶); Blarer et al. (1982 ▶); Juaristi et al. (1993 ▶). For related structures, see: Cobb et al. (2005 ▶), Xu et al. (2007a ▶,b ▶).

Experimental

Crystal data

C14H17NO3

M = 247.29

Monoclinic,

a = 13.4567 (6) Å

b = 8.3618 (4) Å

c = 11.3668 (5) Å

β = 91.734 (4)°

V = 1278.43 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 173 K

0.38 × 0.27 × 0.18 mm

Data collection

Oxford Xcalibur diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006 ▶) T min = 0.986, T max = 1.000

9360 measured reflections

2605 independent reflections

1829 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 0.98

2605 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810045423/ng5052sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810045423/ng5052Isup2.hkl

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

C14H17NO3	F(000) = 528
Mr = 247.29	Dx = 1.285 (1) Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3796 reflections
a = 13.4567 (6) Å	θ = 4.3–26.3°
b = 8.3618 (4) Å	µ = 0.09 mm−1
c = 11.3668 (5) Å	T = 173 K
β = 91.734 (4)°	Block, colourless
V = 1278.43 (10) Å3	0.38 × 0.27 × 0.18 mm
Z = 4

Oxford Xcalibur diffractometer	2605 independent reflections
Radiation source: fine-focus sealed tube	1829 reflections with I > 2σ(I)
graphite	Rint = 0.026
ω scans	θmax = 26.4°, θmin = 4.3°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2006)	h = −16→16
Tmin = 0.986, Tmax = 1.000	k = −10→10
9360 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 0.98	w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3
2605 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.17 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

Experimental. CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

	x	y	z	Uiso*/Ueq
O1	0.27791 (8)	0.45264 (12)	0.27671 (8)	0.0497 (3)
O2	0.30532 (7)	0.25646 (11)	0.39600 (7)	0.0361 (3)
O3	0.46549 (7)	−0.07785 (11)	0.20442 (8)	0.0378 (3)
N1	0.30166 (8)	0.31433 (13)	0.29688 (9)	0.0272 (3)
C1	0.32921 (9)	0.20990 (14)	0.19718 (10)	0.0243 (3)
H1A	0.4012	0.1854	0.2029	0.029*
H1B	0.3155	0.2661	0.1218	0.029*
C2	0.26933 (9)	0.05426 (14)	0.20005 (10)	0.0214 (3)
H2	0.2817	0.0036	0.2788	0.026*
C3	0.30432 (9)	−0.06309 (14)	0.10615 (10)	0.0217 (3)
H3	0.2931	−0.0124	0.0272	0.026*
C4	0.41304 (9)	−0.11083 (15)	0.11829 (11)	0.0258 (3)
C5	0.44795 (10)	−0.21687 (16)	0.02103 (11)	0.0333 (3)
H5A	0.5197	−0.2403	0.0330	0.040*
H5B	0.4383	−0.1623	−0.0558	0.040*
C6	0.38803 (10)	−0.37313 (16)	0.02159 (11)	0.0333 (3)
H6A	0.4068	−0.4406	−0.0458	0.040*
H6B	0.4037	−0.4330	0.0950	0.040*
C7	0.27722 (9)	−0.33748 (16)	0.01310 (11)	0.0325 (3)
H7A	0.2397	−0.4386	0.0205	0.039*
H7B	0.2605	−0.2914	−0.0653	0.039*
C8	0.24528 (10)	−0.22137 (15)	0.10807 (11)	0.0279 (3)
H8A	0.2551	−0.2724	0.1862	0.033*
H8B	0.1735	−0.1978	0.0966	0.033*
C9	0.15860 (9)	0.08735 (14)	0.18614 (10)	0.0220 (3)
C10	0.11872 (9)	0.16173 (15)	0.08584 (10)	0.0298 (3)
H10	0.1618	0.1982	0.0268	0.036*
C11	0.01755 (10)	0.18327 (17)	0.07092 (12)	0.0358 (3)
H11	−0.0082	0.2349	0.0021	0.043*
C12	−0.04660 (10)	0.13068 (16)	0.15475 (12)	0.0368 (4)
H12	−0.1163	0.1439	0.1434	0.044*
C13	−0.00848 (11)	0.05889 (17)	0.25497 (13)	0.0393 (4)
H13	−0.0521	0.0231	0.3136	0.047*
C14	0.09322 (10)	0.03820 (16)	0.27118 (11)	0.0316 (3)
H14	0.1186	−0.0103	0.3415	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0667 (8)	0.0264 (6)	0.0566 (7)	0.0132 (5)	0.0092 (5)	−0.0020 (5)
O2	0.0429 (6)	0.0418 (6)	0.0236 (5)	−0.0013 (5)	0.0033 (4)	−0.0039 (4)
O3	0.0260 (5)	0.0419 (6)	0.0449 (6)	0.0040 (4)	−0.0083 (4)	−0.0096 (5)
N1	0.0240 (6)	0.0270 (6)	0.0306 (6)	−0.0007 (5)	0.0020 (4)	−0.0046 (5)
C1	0.0260 (7)	0.0258 (7)	0.0212 (6)	−0.0004 (6)	0.0048 (5)	−0.0022 (5)
C2	0.0215 (6)	0.0223 (7)	0.0204 (6)	0.0001 (5)	0.0014 (5)	0.0015 (5)
C3	0.0202 (6)	0.0225 (7)	0.0224 (6)	0.0013 (5)	−0.0008 (5)	0.0007 (5)
C4	0.0233 (7)	0.0234 (7)	0.0308 (7)	−0.0014 (6)	0.0026 (5)	0.0010 (5)
C5	0.0247 (7)	0.0381 (8)	0.0373 (7)	0.0055 (6)	0.0055 (6)	−0.0061 (6)
C6	0.0321 (8)	0.0299 (8)	0.0377 (7)	0.0080 (6)	−0.0019 (6)	−0.0082 (6)
C7	0.0309 (8)	0.0269 (7)	0.0395 (8)	0.0019 (6)	−0.0040 (6)	−0.0070 (6)
C8	0.0215 (7)	0.0253 (7)	0.0368 (7)	−0.0004 (6)	0.0004 (5)	−0.0035 (6)
C9	0.0222 (7)	0.0183 (6)	0.0255 (6)	0.0010 (5)	0.0011 (5)	−0.0044 (5)
C10	0.0270 (7)	0.0326 (8)	0.0299 (7)	0.0017 (6)	0.0018 (5)	0.0017 (6)
C11	0.0315 (8)	0.0384 (8)	0.0371 (8)	0.0066 (7)	−0.0052 (6)	0.0032 (6)
C12	0.0202 (7)	0.0360 (8)	0.0540 (9)	0.0061 (6)	−0.0015 (6)	−0.0032 (7)
C13	0.0274 (8)	0.0412 (9)	0.0500 (8)	0.0009 (7)	0.0126 (6)	0.0048 (7)
C14	0.0277 (7)	0.0332 (8)	0.0340 (7)	0.0031 (6)	0.0053 (6)	0.0060 (6)

O1—N1	1.2198 (13)	C6—H6A	0.9900
O2—N1	1.2258 (12)	C6—H6B	0.9900
O3—C4	1.2210 (14)	C7—C8	1.5234 (17)
N1—C1	1.4865 (15)	C7—H7A	0.9900
C1—C2	1.5316 (16)	C7—H7B	0.9900
C1—H1A	0.9900	C8—H8A	0.9900
C1—H1B	0.9900	C8—H8B	0.9900
C2—C9	1.5192 (17)	C9—C14	1.3888 (17)
C2—C3	1.5343 (16)	C9—C10	1.3919 (16)
C2—H2	1.0000	C10—C11	1.3786 (18)
C3—C4	1.5187 (17)	C10—H10	0.9500
C3—C8	1.5442 (16)	C11—C12	1.3770 (19)
C3—H3	1.0000	C11—H11	0.9500
C4—C5	1.5035 (18)	C12—C13	1.3732 (19)
C5—C6	1.5355 (19)	C12—H12	0.9500
C5—H5A	0.9900	C13—C14	1.3862 (19)
C5—H5B	0.9900	C13—H13	0.9500
C6—C7	1.5209 (18)	C14—H14	0.9500
O1—N1—O2	123.37 (10)	C7—C6—H6B	109.6
O1—N1—C1	118.92 (10)	C5—C6—H6B	109.6
O2—N1—C1	117.70 (10)	H6A—C6—H6B	108.1
N1—C1—C2	109.84 (9)	C6—C7—C8	112.15 (10)
N1—C1—H1A	109.7	C6—C7—H7A	109.2
C2—C1—H1A	109.7	C8—C7—H7A	109.2
N1—C1—H1B	109.7	C6—C7—H7B	109.2
C2—C1—H1B	109.7	C8—C7—H7B	109.2
H1A—C1—H1B	108.2	H7A—C7—H7B	107.9
C9—C2—C1	110.98 (10)	C7—C8—C3	112.33 (10)
C9—C2—C3	111.39 (9)	C7—C8—H8A	109.1
C1—C2—C3	110.85 (9)	C3—C8—H8A	109.1
C9—C2—H2	107.8	C7—C8—H8B	109.1
C1—C2—H2	107.8	C3—C8—H8B	109.1
C3—C2—H2	107.8	H8A—C8—H8B	107.9
C4—C3—C2	114.83 (9)	C14—C9—C10	117.75 (12)
C4—C3—C8	105.55 (10)	C14—C9—C2	120.91 (10)
C2—C3—C8	111.68 (10)	C10—C9—C2	121.29 (11)
C4—C3—H3	108.2	C11—C10—C9	120.93 (12)
C2—C3—H3	108.2	C11—C10—H10	119.5
C8—C3—H3	108.2	C9—C10—H10	119.5
O3—C4—C5	122.47 (12)	C12—C11—C10	120.70 (12)
O3—C4—C3	123.05 (11)	C12—C11—H11	119.7
C5—C4—C3	114.19 (11)	C10—C11—H11	119.7
C4—C5—C6	108.84 (11)	C13—C12—C11	119.17 (13)
C4—C5—H5A	109.9	C13—C12—H12	120.4
C6—C5—H5A	109.9	C11—C12—H12	120.4
C4—C5—H5B	109.9	C12—C13—C14	120.48 (13)
C6—C5—H5B	109.9	C12—C13—H13	119.8
H5A—C5—H5B	108.3	C14—C13—H13	119.8
C7—C6—C5	110.30 (11)	C13—C14—C9	120.94 (12)
C7—C6—H6A	109.6	C13—C14—H14	119.5
C5—C6—H6A	109.6	C9—C14—H14	119.5
O1—N1—C1—C2	−128.32 (12)	C6—C7—C8—C3	56.07 (15)
O2—N1—C1—C2	52.56 (14)	C4—C3—C8—C7	−56.14 (13)
N1—C1—C2—C9	61.75 (12)	C2—C3—C8—C7	178.44 (10)
N1—C1—C2—C3	−173.91 (9)	C1—C2—C9—C14	−122.22 (12)
C9—C2—C3—C4	−176.37 (10)	C3—C2—C9—C14	113.75 (13)
C1—C2—C3—C4	59.53 (13)	C1—C2—C9—C10	60.49 (14)
C9—C2—C3—C8	−56.26 (13)	C3—C2—C9—C10	−63.53 (15)
C1—C2—C3—C8	179.64 (9)	C14—C9—C10—C11	−1.04 (19)
C2—C3—C4—O3	10.01 (17)	C2—C9—C10—C11	176.33 (11)
C8—C3—C4—O3	−113.44 (13)	C9—C10—C11—C12	−0.4 (2)
C2—C3—C4—C5	−176.03 (10)	C10—C11—C12—C13	1.2 (2)
C8—C3—C4—C5	60.52 (13)	C11—C12—C13—C14	−0.6 (2)
O3—C4—C5—C6	112.56 (13)	C12—C13—C14—C9	−0.9 (2)
C3—C4—C5—C6	−61.43 (14)	C10—C9—C14—C13	1.68 (19)
C4—C5—C6—C7	55.04 (14)	C2—C9—C14—C13	−175.70 (12)
C5—C6—C7—C8	−53.99 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O2i	0.99	2.57	3.4403 (14)	146
C5—H5A···O2ii	0.99	2.47	3.4312 (16)	165
C8—H8A···O1iii	0.99	2.53	3.3536 (16)	140
C10—H10···O2i	0.95	2.50	3.4289 (15)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O2i	0.99	2.57	3.4403 (14)	146
C5—H5A⋯O2ii	0.99	2.47	3.4312 (16)	165
C8—H8A⋯O1iii	0.99	2.53	3.3536 (16)	140
C10—H10⋯O2i	0.95	2.50	3.4289 (15)	165

Symmetry codes: (i) ; (ii) ; (iii) .