Ethyl 4-(2-hydroxy-ethyl-amino)-3-nitro-benzoate.

In the title compound, C(11)H(14)N(2)O(5), the mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond, which generates an S(6) ring motif. The nitro group is twisted slightly from the attached benzene ring, forming a dihedral angle of 5.2 (2)°. In the crystal packing, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. The crystal studied was a non-merohedral twin, the refined ratio of the twin components being 0.264 (2):0.736 (2).

Related literature

For background to benzimidazoles, see: Mayer et al. (1998 ▶); Brouillette et al. (1999 ▶); Williams et al. (1995 ▶); Wright (1951 ▶). For reference bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Narendra Babu, Abdul Rahim, Abd Hamid et al. (2009 ▶); Narendra Babu, Abdul Rahim, Osman et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C11H14N2O5

M = 254.24

Monoclinic,

a = 10.6422 (6) Å

b = 14.9954 (9) Å

c = 7.1975 (4) Å

β = 99.607 (2)°

V = 1132.50 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.43 × 0.13 × 0.03 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 209 ▶0) T min = 0.951, T max = 0.997

8457 measured reflections

2587 independent reflections

2026 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.129

S = 1.04

2587 reflections

173 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810008147/wn2377sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810008147/wn2377Isup2.hkl

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

C11H14N2O5	F(000) = 536
Mr = 254.24	Dx = 1.491 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1880 reflections
a = 10.6422 (6) Å	θ = 2.4–28.1°
b = 14.9954 (9) Å	µ = 0.12 mm−1
c = 7.1975 (4) Å	T = 100 K
β = 99.607 (2)°	Needle, yellow
V = 1132.50 (11) Å3	0.43 × 0.13 × 0.03 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2587 independent reflections
Radiation source: fine-focus sealed tube	2026 reflections with I > 2σ(I)
graphite	Rint = 0.050
φ and ω scans	θmax = 27.5°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2090)	h = −13→13
Tmin = 0.951, Tmax = 0.997	k = −19→19
8457 measured reflections	l = −8→9

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0602P)2 + 0.3204P] where P = (Fo2 + 2Fc2)/3
2587 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 0.50 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O1	0.38669 (15)	0.04338 (11)	1.1300 (3)	0.0285 (4)
O2	0.57298 (13)	0.09227 (10)	1.2508 (2)	0.0193 (4)
O3	0.04479 (14)	0.22764 (10)	0.8325 (2)	0.0194 (4)
O4	0.07343 (13)	0.37665 (10)	0.8413 (2)	0.0170 (4)
O5	0.82105 (15)	0.33071 (11)	1.0883 (2)	0.0192 (4)
N1	0.46108 (17)	0.10564 (12)	1.1729 (3)	0.0157 (4)
N2	0.61527 (17)	0.26565 (12)	1.2825 (3)	0.0147 (4)
C1	0.29266 (19)	0.20462 (14)	1.0362 (3)	0.0141 (5)
H1A	0.2445	0.1539	0.9998	0.017*
C2	0.4166 (2)	0.19539 (14)	1.1327 (3)	0.0135 (4)
C3	0.49466 (19)	0.27115 (14)	1.1919 (3)	0.0135 (4)
C4	0.43542 (19)	0.35571 (14)	1.1508 (3)	0.0148 (5)
H4A	0.4811	0.4071	1.1901	0.018*
C5	0.3135 (2)	0.36374 (14)	1.0555 (3)	0.0148 (5)
H5A	0.2784	0.4202	1.0308	0.018*
C6	0.2402 (2)	0.28743 (14)	0.9938 (3)	0.0150 (5)
C7	0.11002 (19)	0.29283 (14)	0.8828 (3)	0.0148 (5)
C8	−0.05110 (19)	0.38757 (14)	0.7226 (3)	0.0168 (5)
H8A	−0.1143	0.3517	0.7709	0.020*
H8B	−0.0473	0.3685	0.5949	0.020*
C9	−0.0866 (2)	0.48440 (16)	0.7242 (4)	0.0254 (6)
H9A	−0.1695	0.4929	0.6501	0.038*
H9B	−0.0251	0.5192	0.6722	0.038*
H9C	−0.0879	0.5031	0.8515	0.038*
C10	0.69687 (19)	0.34151 (14)	1.3465 (3)	0.0142 (4)
H10A	0.7673	0.3210	1.4400	0.017*
H10B	0.6484	0.3841	1.4073	0.017*
C11	0.75012 (19)	0.38863 (14)	1.1886 (3)	0.0157 (5)
H11A	0.6801	0.4141	1.1011	0.019*
H11B	0.8047	0.4372	1.2419	0.019*
H2A	0.642 (2)	0.2141 (18)	1.310 (4)	0.021 (7)*
H5B	0.888 (3)	0.3148 (18)	1.156 (4)	0.028 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0224 (8)	0.0119 (8)	0.0480 (12)	−0.0046 (7)	−0.0035 (8)	0.0003 (8)
O2	0.0169 (8)	0.0143 (8)	0.0252 (9)	0.0027 (6)	−0.0004 (7)	0.0010 (7)
O3	0.0145 (7)	0.0177 (8)	0.0243 (9)	−0.0040 (6)	−0.0011 (7)	0.0005 (7)
O4	0.0118 (7)	0.0168 (8)	0.0207 (9)	0.0003 (6)	−0.0024 (6)	0.0005 (7)
O5	0.0149 (8)	0.0216 (9)	0.0204 (9)	0.0025 (6)	0.0012 (7)	−0.0020 (7)
N1	0.0146 (9)	0.0129 (9)	0.0192 (10)	−0.0015 (7)	0.0018 (7)	−0.0009 (8)
N2	0.0116 (8)	0.0115 (9)	0.0201 (10)	0.0007 (7)	0.0002 (8)	0.0017 (8)
C1	0.0153 (11)	0.0145 (10)	0.0130 (11)	−0.0038 (8)	0.0036 (8)	−0.0026 (9)
C2	0.0151 (10)	0.0119 (10)	0.0144 (11)	−0.0002 (8)	0.0051 (8)	0.0017 (8)
C3	0.0145 (10)	0.0142 (11)	0.0118 (11)	−0.0018 (8)	0.0029 (8)	−0.0001 (8)
C4	0.0135 (10)	0.0123 (10)	0.0188 (12)	−0.0012 (8)	0.0030 (8)	−0.0016 (9)
C5	0.0169 (10)	0.0128 (10)	0.0147 (11)	0.0014 (8)	0.0027 (8)	0.0010 (9)
C6	0.0132 (10)	0.0165 (11)	0.0156 (11)	0.0003 (8)	0.0030 (9)	0.0013 (9)
C7	0.0148 (10)	0.0159 (11)	0.0144 (11)	−0.0004 (8)	0.0045 (9)	0.0007 (9)
C8	0.0116 (10)	0.0203 (11)	0.0161 (11)	0.0004 (8)	−0.0045 (9)	0.0015 (9)
C9	0.0198 (11)	0.0226 (13)	0.0301 (14)	0.0053 (9)	−0.0069 (10)	−0.0019 (11)
C10	0.0116 (9)	0.0147 (10)	0.0148 (11)	−0.0009 (8)	−0.0017 (8)	−0.0004 (9)
C11	0.0127 (10)	0.0128 (10)	0.0208 (11)	−0.0013 (8)	0.0005 (9)	−0.0004 (9)

O1—N1	1.230 (2)	C4—C5	1.368 (3)
O2—N1	1.245 (2)	C4—H4A	0.9300
O3—C7	1.218 (3)	C5—C6	1.414 (3)
O4—C7	1.335 (3)	C5—H5A	0.9300
O4—C8	1.461 (2)	C6—C7	1.482 (3)
O5—C11	1.424 (3)	C8—C9	1.501 (3)
O5—H5B	0.83 (3)	C8—H8A	0.9700
N1—C2	1.440 (3)	C8—H8B	0.9700
N2—C3	1.342 (3)	C9—H9A	0.9600
N2—C10	1.459 (3)	C9—H9B	0.9600
N2—H2A	0.84 (3)	C9—H9C	0.9600
C1—C6	1.375 (3)	C10—C11	1.526 (3)
C1—C2	1.391 (3)	C10—H10A	0.9700
C1—H1A	0.9300	C10—H10B	0.9700
C2—C3	1.430 (3)	C11—H11A	0.9700
C3—C4	1.425 (3)	C11—H11B	0.9700
C7—O4—C8	116.01 (16)	O3—C7—C6	123.46 (19)
C11—O5—H5B	110 (2)	O4—C7—C6	112.56 (18)
O1—N1—O2	121.21 (17)	O4—C8—C9	107.99 (17)
O1—N1—C2	118.86 (17)	O4—C8—H8A	110.1
O2—N1—C2	119.92 (17)	C9—C8—H8A	110.1
C3—N2—C10	125.21 (19)	O4—C8—H8B	110.1
C3—N2—H2A	115.5 (18)	C9—C8—H8B	110.1
C10—N2—H2A	119.1 (18)	H8A—C8—H8B	108.4
C6—C1—C2	121.12 (19)	C8—C9—H9A	109.5
C6—C1—H1A	119.4	C8—C9—H9B	109.5
C2—C1—H1A	119.4	H9A—C9—H9B	109.5
C1—C2—C3	121.68 (19)	C8—C9—H9C	109.5
C1—C2—N1	116.49 (18)	H9A—C9—H9C	109.5
C3—C2—N1	121.82 (19)	H9B—C9—H9C	109.5
N2—C3—C4	120.65 (19)	N2—C10—C11	113.65 (18)
N2—C3—C2	123.9 (2)	N2—C10—H10A	108.8
C4—C3—C2	115.47 (18)	C11—C10—H10A	108.8
C5—C4—C3	122.1 (2)	N2—C10—H10B	108.8
C5—C4—H4A	118.9	C11—C10—H10B	108.8
C3—C4—H4A	118.9	H10A—C10—H10B	107.7
C4—C5—C6	120.9 (2)	O5—C11—C10	112.94 (18)
C4—C5—H5A	119.5	O5—C11—H11A	109.0
C6—C5—H5A	119.5	C10—C11—H11A	109.0
C1—C6—C5	118.61 (19)	O5—C11—H11B	109.0
C1—C6—C7	118.53 (19)	C10—C11—H11B	109.0
C5—C6—C7	122.85 (19)	H11A—C11—H11B	107.8
O3—C7—O4	123.96 (19)
C6—C1—C2—C3	0.0 (3)	C3—C4—C5—C6	0.3 (3)
C6—C1—C2—N1	178.9 (2)	C2—C1—C6—C5	−1.9 (3)
O1—N1—C2—C1	−3.9 (3)	C2—C1—C6—C7	177.1 (2)
O2—N1—C2—C1	176.5 (2)	C4—C5—C6—C1	1.8 (3)
O1—N1—C2—C3	175.0 (2)	C4—C5—C6—C7	−177.2 (2)
O2—N1—C2—C3	−4.6 (3)	C8—O4—C7—O3	−2.2 (3)
C10—N2—C3—C4	−0.1 (3)	C8—O4—C7—C6	176.60 (18)
C10—N2—C3—C2	−179.3 (2)	C1—C6—C7—O3	2.8 (3)
C1—C2—C3—N2	−178.8 (2)	C5—C6—C7—O3	−178.3 (2)
N1—C2—C3—N2	2.4 (3)	C1—C6—C7—O4	−176.1 (2)
C1—C2—C3—C4	2.0 (3)	C5—C6—C7—O4	2.9 (3)
N1—C2—C3—C4	−176.81 (19)	C7—O4—C8—C9	168.7 (2)
N2—C3—C4—C5	178.7 (2)	C3—N2—C10—C11	−76.3 (3)
C2—C3—C4—C5	−2.1 (3)	N2—C10—C11—O5	−57.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2	0.84 (3)	1.99 (3)	2.642 (2)	134 (2)
O5—H5B···O3i	0.83 (3)	2.02 (3)	2.851 (2)	177 (3)
C8—H8A···O5ii	0.97	2.51	3.271 (3)	135
C10—H10A···O5iii	0.97	2.54	3.267 (3)	132
C10—H10B···O1iv	0.97	2.43	3.168 (3)	133
C11—H11A···O2v	0.97	2.59	3.403 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2	0.84 (3)	1.99 (3)	2.642 (2)	134 (2)
O5—H5B⋯O3i	0.83 (3)	2.02 (3)	2.851 (2)	177 (3)
C8—H8A⋯O5ii	0.97	2.51	3.271 (3)	135
C10—H10A⋯O5iii	0.97	2.54	3.267 (3)	132
C10—H10B⋯O1iv	0.97	2.43	3.168 (3)	133
C11—H11A⋯O2v	0.97	2.59	3.403 (3)	142

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