2-[1-(4-Bromo-phen-yl)-2-nitro-eth-yl]hexa-noic acid.

In the crystal structure of the title compoud, C14H18BrNO4, mol-ecules are linked by a strong O-H⋯O hydrogen bond and weaker C-H⋯O inter-actions. The benzene ring makes dihedral angles of 3.67 (3) and 72.63 (3)° with the carb-oxy-lic acid group and the nitro group, respectively.

Related literature

For related compounds, see: Wu et al. (2011 ▶); Nayak et al. (2013 ▶); Zhang et al. (2013 ▶); Thirunavukkarasu et al. (2014 ▶). For the asymmetric Michael reaction, which allows for the formation of two asymmetric centres, see: Enders et al. (2002 ▶); Hayashi et al. (2005 ▶); Keller et al. (2013 ▶).

Experimental

Crystal data

C14H18BrNO4

M = 344.20

Triclinic,

a = 7.2825 (11) Å

b = 8.7850 (13) Å

c = 13.026 (2) Å

α = 107.882 (3)°

β = 93.156 (3)°

γ = 101.555 (3)°

V = 770.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.68 mm−1

T = 140 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.510, T max = 0.746

7818 measured reflections

4717 independent reflections

3078 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.113

S = 0.99

4717 reflections

182 parameters

H-atom parameters constrained

Δρmax = 0.77 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) General, I. DOI: 10.1107/S1600536814006941/fj2666sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006941/fj2666Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006941/fj2666Isup3.cml

CCDC reference: 994185

Additional supporting information: crystallographic information; 3D view; checkCIF report

C14H18BrNO4	Z = 2
Mr = 344.20	F(000) = 352
Triclinic, P1	Dx = 1.483 Mg m−3
a = 7.2825 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7850 (13) Å	Cell parameters from 1805 reflections
c = 13.026 (2) Å	θ = 2.5–27.0°
α = 107.882 (3)°	µ = 2.68 mm−1
β = 93.156 (3)°	T = 140 K
γ = 101.555 (3)°	Block, colourless
V = 770.9 (2) Å3	0.25 × 0.20 × 0.15 mm

Bruker APEXII CCD diffractometer	3078 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.026
Absorption correction: multi-scan (SADABS; Bruker, 2004)	θmax = 30.7°, θmin = 1.7°
Tmin = 0.510, Tmax = 0.746	h = −7→10
7818 measured reflections	k = −12→11
4717 independent reflections	l = −18→18

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045	H-atom parameters constrained
wR(F2) = 0.113	w = 1/[σ2(Fo2) + (0.0579P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.005
4717 reflections	Δρmax = 0.77 e Å−3
182 parameters	Δρmin = −0.57 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 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.

	x	y	z	Uiso*/Ueq
Br1	0.43884 (4)	0.25204 (4)	1.00399 (2)	0.04824 (13)
N1	−0.2878 (3)	−0.0037 (2)	0.57284 (16)	0.0281 (4)
O1	−0.2159 (3)	−0.1173 (2)	0.53116 (18)	0.0503 (5)
O2	−0.4281 (3)	−0.0168 (2)	0.61913 (17)	0.0433 (5)
O3	−0.2581 (2)	0.5058 (2)	0.50126 (13)	0.0309 (4)
H3A	−0.3560	0.5143	0.4683	0.046*
O4	−0.4590 (2)	0.4623 (2)	0.61743 (15)	0.0363 (4)
C1	−0.2028 (3)	0.1613 (3)	0.56541 (18)	0.0239 (5)
H1A	−0.2850	0.1860	0.5125	0.029*
H1B	−0.0781	0.1604	0.5389	0.029*
C2	−0.1790 (3)	0.2947 (3)	0.67608 (17)	0.0211 (4)
H2	−0.3015	0.2804	0.7070	0.025*
C3	−0.1361 (3)	0.4661 (3)	0.66194 (17)	0.0222 (4)
H3	−0.0170	0.4809	0.6278	0.027*
C4	−0.2969 (3)	0.4783 (3)	0.58874 (18)	0.0232 (5)
C5	−0.1128 (4)	0.6028 (3)	0.77204 (18)	0.0271 (5)
H5A	−0.2300	0.5861	0.8062	0.033*
H5B	−0.0086	0.5936	0.8202	0.033*
C6	−0.0709 (4)	0.7759 (3)	0.7638 (2)	0.0340 (6)
H6A	−0.1778	0.7865	0.7182	0.041*
H6B	−0.0629	0.8560	0.8374	0.041*
C7	0.1105 (4)	0.8203 (3)	0.7162 (2)	0.0393 (6)
H7A	0.1270	0.9341	0.7145	0.047*
H7B	0.0984	0.7465	0.6403	0.047*
C8	0.2860 (5)	0.8075 (4)	0.7796 (3)	0.0547 (8)
H8A	0.2911	0.8700	0.8567	0.082*
H8B	0.3990	0.8524	0.7513	0.082*
H8C	0.2806	0.6920	0.7714	0.082*
C9	−0.0284 (3)	0.2792 (3)	0.75450 (17)	0.0208 (4)
C10	0.1607 (3)	0.3049 (3)	0.73681 (19)	0.0262 (5)
H10	0.1946	0.3273	0.6727	0.031*
C11	0.2991 (3)	0.2982 (3)	0.8106 (2)	0.0305 (5)
H11	0.4278	0.3183	0.7984	0.037*
C12	0.2485 (4)	0.2619 (3)	0.90266 (19)	0.0305 (5)
C13	0.0628 (4)	0.2332 (3)	0.92160 (19)	0.0304 (5)
H13	0.0295	0.2076	0.9848	0.036*
C14	−0.0752 (3)	0.2422 (3)	0.84734 (18)	0.0260 (5)
H14	−0.2036	0.2226	0.8602	0.031*

	U11	U22	U33	U12	U13	U23
Br1	0.04362 (18)	0.0746 (2)	0.02979 (15)	0.03115 (16)	−0.00597 (11)	0.01222 (14)
N1	0.0289 (11)	0.0264 (11)	0.0266 (10)	0.0030 (9)	−0.0045 (8)	0.0088 (8)
O1	0.0634 (14)	0.0274 (11)	0.0616 (14)	0.0184 (10)	0.0132 (11)	0.0107 (9)
O2	0.0374 (11)	0.0417 (11)	0.0495 (12)	−0.0013 (9)	0.0085 (9)	0.0192 (9)
O3	0.0297 (9)	0.0443 (10)	0.0287 (9)	0.0175 (8)	0.0073 (7)	0.0199 (8)
O4	0.0251 (9)	0.0576 (12)	0.0373 (10)	0.0159 (8)	0.0081 (7)	0.0263 (9)
C1	0.0245 (11)	0.0237 (12)	0.0240 (11)	0.0047 (9)	0.0021 (9)	0.0092 (9)
C2	0.0201 (10)	0.0251 (12)	0.0200 (10)	0.0068 (9)	0.0023 (8)	0.0089 (9)
C3	0.0220 (10)	0.0262 (12)	0.0214 (10)	0.0085 (9)	0.0019 (8)	0.0104 (9)
C4	0.0272 (11)	0.0216 (12)	0.0227 (11)	0.0098 (9)	0.0024 (9)	0.0075 (9)
C5	0.0350 (13)	0.0258 (12)	0.0227 (11)	0.0098 (10)	0.0049 (10)	0.0090 (9)
C6	0.0533 (17)	0.0231 (12)	0.0267 (12)	0.0128 (11)	0.0001 (11)	0.0077 (10)
C7	0.0575 (18)	0.0270 (14)	0.0333 (14)	0.0037 (12)	0.0011 (13)	0.0140 (11)
C8	0.0475 (18)	0.055 (2)	0.060 (2)	−0.0039 (15)	−0.0035 (16)	0.0280 (17)
C9	0.0225 (10)	0.0198 (11)	0.0209 (10)	0.0072 (8)	0.0014 (8)	0.0065 (8)
C10	0.0244 (11)	0.0332 (13)	0.0236 (11)	0.0080 (10)	0.0051 (9)	0.0117 (10)
C11	0.0212 (11)	0.0392 (14)	0.0325 (13)	0.0111 (10)	0.0038 (9)	0.0112 (11)
C12	0.0318 (12)	0.0360 (14)	0.0235 (11)	0.0162 (10)	−0.0033 (9)	0.0050 (10)
C13	0.0375 (14)	0.0368 (14)	0.0222 (11)	0.0143 (11)	0.0039 (10)	0.0136 (10)
C14	0.0254 (11)	0.0322 (13)	0.0243 (11)	0.0091 (10)	0.0062 (9)	0.0124 (10)

Br1—C12	1.894 (2)	C6—C7	1.521 (4)
N1—O1	1.213 (3)	C6—H6A	0.9900
N1—O2	1.218 (3)	C6—H6B	0.9900
N1—C1	1.492 (3)	C7—C8	1.525 (4)
O3—C4	1.270 (3)	C7—H7A	0.9900
O3—H3A	0.8400	C7—H7B	0.9900
O4—C4	1.252 (3)	C8—H8A	0.9800
C1—C2	1.528 (3)	C8—H8B	0.9800
C1—H1A	0.9900	C8—H8C	0.9800
C1—H1B	0.9900	C9—C14	1.388 (3)
C2—C9	1.512 (3)	C9—C10	1.394 (3)
C2—C3	1.545 (3)	C10—C11	1.377 (3)
C2—H2	1.0000	C10—H10	0.9500
C3—C4	1.511 (3)	C11—C12	1.383 (3)
C3—C5	1.537 (3)	C11—H11	0.9500
C3—H3	1.0000	C12—C13	1.375 (4)
C5—C6	1.528 (3)	C13—C14	1.387 (3)
C5—H5A	0.9900	C13—H13	0.9500
C5—H5B	0.9900	C14—H14	0.9500
O1—N1—O2	123.8 (2)	C7—C6—H6B	108.7
O1—N1—C1	118.5 (2)	C5—C6—H6B	108.7
O2—N1—C1	117.7 (2)	H6A—C6—H6B	107.6
C4—O3—H3A	109.5	C6—C7—C8	113.6 (2)
N1—C1—C2	110.98 (18)	C6—C7—H7A	108.9
N1—C1—H1A	109.4	C8—C7—H7A	108.9
C2—C1—H1A	109.4	C6—C7—H7B	108.9
N1—C1—H1B	109.4	C8—C7—H7B	108.9
C2—C1—H1B	109.4	H7A—C7—H7B	107.7
H1A—C1—H1B	108.0	C7—C8—H8A	109.5
C9—C2—C1	111.47 (17)	C7—C8—H8B	109.5
C9—C2—C3	111.60 (17)	H8A—C8—H8B	109.5
C1—C2—C3	109.94 (17)	C7—C8—H8C	109.5
C9—C2—H2	107.9	H8A—C8—H8C	109.5
C1—C2—H2	107.9	H8B—C8—H8C	109.5
C3—C2—H2	107.9	C14—C9—C10	118.4 (2)
C4—C3—C5	108.96 (17)	C14—C9—C2	120.5 (2)
C4—C3—C2	109.26 (18)	C10—C9—C2	121.08 (19)
C5—C3—C2	111.06 (17)	C11—C10—C9	121.2 (2)
C4—C3—H3	109.2	C11—C10—H10	119.4
C5—C3—H3	109.2	C9—C10—H10	119.4
C2—C3—H3	109.2	C10—C11—C12	119.2 (2)
O4—C4—O3	123.8 (2)	C10—C11—H11	120.4
O4—C4—C3	118.8 (2)	C12—C11—H11	120.4
O3—C4—C3	117.3 (2)	C13—C12—C11	121.0 (2)
C6—C5—C3	113.78 (19)	C13—C12—Br1	119.74 (19)
C6—C5—H5A	108.8	C11—C12—Br1	119.22 (19)
C3—C5—H5A	108.8	C12—C13—C14	119.3 (2)
C6—C5—H5B	108.8	C12—C13—H13	120.4
C3—C5—H5B	108.8	C14—C13—H13	120.4
H5A—C5—H5B	107.7	C13—C14—C9	120.9 (2)
C7—C6—C5	114.3 (2)	C13—C14—H14	119.5
C7—C6—H6A	108.7	C9—C14—H14	119.5
C5—C6—H6A	108.7
O1—N1—C1—C2	−132.7 (2)	C5—C6—C7—C8	−58.1 (3)
O2—N1—C1—C2	48.5 (3)	C1—C2—C9—C14	−115.2 (2)
N1—C1—C2—C9	69.0 (2)	C3—C2—C9—C14	121.5 (2)
N1—C1—C2—C3	−166.69 (17)	C1—C2—C9—C10	66.1 (3)
C9—C2—C3—C4	−176.36 (17)	C3—C2—C9—C10	−57.2 (3)
C1—C2—C3—C4	59.4 (2)	C14—C9—C10—C11	−1.7 (3)
C9—C2—C3—C5	−56.1 (2)	C2—C9—C10—C11	177.0 (2)
C1—C2—C3—C5	179.63 (18)	C9—C10—C11—C12	1.4 (4)
C5—C3—C4—O4	−61.1 (3)	C10—C11—C12—C13	−0.3 (4)
C2—C3—C4—O4	60.4 (3)	C10—C11—C12—Br1	179.80 (18)
C5—C3—C4—O3	118.3 (2)	C11—C12—C13—C14	−0.5 (4)
C2—C3—C4—O3	−120.2 (2)	Br1—C12—C13—C14	179.44 (18)
C4—C3—C5—C6	−59.3 (3)	C12—C13—C14—C9	0.1 (4)
C2—C3—C5—C6	−179.7 (2)	C10—C9—C14—C13	0.9 (3)
C3—C5—C6—C7	−60.6 (3)	C2—C9—C14—C13	−177.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1B···O1i	0.99	2.43	3.410 (3)	172
C1—H1A···O2ii	0.99	2.51	3.265 (3)	133
C3—H3···O3iii	1.00	2.69	3.679 (3)	169
C8—H8B···O2iv	0.98	2.60	3.501 (4)	153
O3—H3A···O4v	0.84	1.79	2.619 (2)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1B⋯O1i	0.99	2.43	3.410 (3)	172
C1—H1A⋯O2ii	0.99	2.51	3.265 (3)	133
C3—H3⋯O3iii	1.00	2.69	3.679 (3)	169
C8—H8B⋯O2iv	0.98	2.60	3.501 (4)	153
O3—H3A⋯O4v	0.84	1.79	2.619 (2)	171

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