Ethyl 4-anilino-3-nitro-benzoate.

In the title compound, C(15)H(14)N(2)O(4), the dihedral angle between the benzene and phenyl rings is 73.20 (6)°. An intra-molecular N-H⋯O hydrogen bond forms an S(6) ring motif. In the crystal, mol-ecules are linked by N-H⋯O and C-H⋯O hydrogen bonds into a layer parallel to the bc plane.

Related literature

For applications of nitro­phenyl­ene­amines, see: Stephane (2006 ▶); Glebowska et al. (2009 ▶); Remusat et al. (2004 ▶). For related structures, see: Mohdaidin et al. (2008 ▶); Zhang 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

C15H14N2O4

M = 286.28

Monoclinic,

a = 10.6464 (2) Å

b = 9.9178 (2) Å

c = 14.7885 (2) Å

β = 120.244 (1)°

V = 1348.96 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.35 × 0.20 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.965, T max = 0.984

17988 measured reflections

4639 independent reflections

3276 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.04

4639 reflections

195 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.26 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 datablock(s) global, I. DOI: 10.1107/S1600536812019903/is5128sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019903/is5128Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812019903/is5128Isup3.cml

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3629 reflections
a = 10.6464 (2) Å	θ = 2.9–31.4°
b = 9.9178 (2) Å	µ = 0.10 mm−1
c = 14.7885 (2) Å	T = 100 K
β = 120.244 (1)°	Block, yellow
V = 1348.96 (4) Å3	0.35 × 0.20 × 0.16 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	4639 independent reflections
Radiation source: fine-focus sealed tube	3276 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
φ and ω scans	θmax = 31.9°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −15→15
Tmin = 0.965, Tmax = 0.984	k = −14→14
17988 measured reflections	l = −21→21

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0561P)2 + 0.2709P] where P = (Fo2 + 2Fc2)/3
4639 reflections	(Δ/σ)max = 0.001
195 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.26 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 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
O1	0.28632 (10)	−0.12818 (8)	0.76247 (7)	0.01976 (19)
O2	0.46453 (10)	0.00161 (9)	0.76921 (7)	0.0212 (2)
O3	0.66947 (10)	0.34436 (10)	1.03221 (8)	0.0273 (2)
O4	0.55970 (10)	0.42674 (9)	1.10945 (8)	0.0228 (2)
N1	0.33488 (11)	0.29963 (10)	1.09858 (8)	0.0181 (2)
N2	0.56820 (11)	0.34349 (10)	1.05006 (8)	0.0184 (2)
C1	0.46344 (13)	0.16060 (11)	0.92632 (9)	0.0165 (2)
H1A	0.5353	0.1764	0.9095	0.020*
C2	0.45671 (12)	0.24143 (11)	1.00074 (9)	0.0154 (2)
C3	0.34771 (13)	0.22195 (11)	1.02854 (9)	0.0153 (2)
C4	0.24935 (13)	0.11392 (12)	0.97700 (9)	0.0169 (2)
H4A	0.1767	0.0968	0.9929	0.020*
C5	0.25813 (13)	0.03416 (12)	0.90452 (10)	0.0173 (2)
H5A	0.1924	−0.0362	0.8730	0.021*
C6	0.36523 (13)	0.05748 (11)	0.87723 (9)	0.0161 (2)
C7	0.37913 (13)	−0.02319 (12)	0.79882 (10)	0.0173 (2)
C8	0.29118 (15)	−0.20792 (13)	0.68146 (11)	0.0239 (3)
H8A	0.3826	−0.2563	0.7107	0.029*
H8B	0.2825	−0.1497	0.6259	0.029*
C9	0.16782 (18)	−0.30447 (14)	0.63980 (12)	0.0324 (3)
H9A	0.1677	−0.3582	0.5858	0.049*
H9B	0.0780	−0.2555	0.6114	0.049*
H9C	0.1780	−0.3620	0.6953	0.049*
C10	0.23046 (13)	0.27774 (12)	1.13077 (10)	0.0175 (2)
C11	0.11792 (14)	0.37011 (13)	1.10012 (11)	0.0227 (3)
H11A	0.1090	0.4418	1.0567	0.027*
C12	0.01887 (15)	0.35537 (14)	1.13428 (12)	0.0281 (3)
H12A	−0.0559	0.4176	1.1143	0.034*
C13	0.03126 (15)	0.24804 (14)	1.19810 (12)	0.0287 (3)
H13A	−0.0359	0.2374	1.2202	0.034*
C14	0.14412 (16)	0.15626 (14)	1.22907 (12)	0.0269 (3)
H14A	0.1528	0.0846	1.2724	0.032*
C15	0.24447 (15)	0.17090 (12)	1.19555 (11)	0.0218 (3)
H15A	0.3202	0.1095	1.2165	0.026*
H1N1	0.3899 (19)	0.3693 (16)	1.1227 (13)	0.030 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0247 (5)	0.0208 (4)	0.0188 (5)	0.0008 (3)	0.0147 (4)	−0.0030 (3)
O2	0.0237 (5)	0.0249 (4)	0.0222 (5)	0.0049 (3)	0.0169 (4)	0.0034 (4)
O3	0.0211 (5)	0.0350 (5)	0.0342 (6)	−0.0065 (4)	0.0202 (4)	−0.0053 (4)
O4	0.0259 (5)	0.0229 (4)	0.0250 (5)	−0.0052 (4)	0.0169 (4)	−0.0054 (4)
N1	0.0189 (5)	0.0194 (5)	0.0218 (6)	−0.0037 (4)	0.0146 (4)	−0.0049 (4)
N2	0.0176 (5)	0.0211 (5)	0.0193 (5)	−0.0010 (4)	0.0113 (4)	0.0013 (4)
C1	0.0172 (5)	0.0188 (5)	0.0176 (6)	0.0039 (4)	0.0119 (5)	0.0048 (4)
C2	0.0151 (5)	0.0172 (5)	0.0163 (6)	0.0000 (4)	0.0096 (5)	0.0011 (4)
C3	0.0153 (5)	0.0176 (5)	0.0153 (6)	0.0018 (4)	0.0092 (4)	0.0011 (4)
C4	0.0157 (5)	0.0211 (5)	0.0172 (6)	−0.0009 (4)	0.0107 (5)	−0.0005 (4)
C5	0.0176 (5)	0.0191 (5)	0.0167 (6)	−0.0001 (4)	0.0098 (5)	−0.0005 (4)
C6	0.0182 (5)	0.0187 (5)	0.0146 (6)	0.0036 (4)	0.0107 (5)	0.0025 (4)
C7	0.0195 (6)	0.0183 (5)	0.0162 (6)	0.0050 (4)	0.0106 (5)	0.0037 (4)
C8	0.0314 (7)	0.0249 (6)	0.0208 (7)	0.0044 (5)	0.0171 (6)	−0.0038 (5)
C9	0.0428 (9)	0.0279 (7)	0.0307 (8)	−0.0050 (6)	0.0217 (7)	−0.0078 (6)
C10	0.0157 (5)	0.0222 (5)	0.0183 (6)	−0.0038 (4)	0.0113 (5)	−0.0063 (5)
C11	0.0181 (6)	0.0273 (6)	0.0227 (7)	0.0004 (5)	0.0104 (5)	−0.0031 (5)
C12	0.0181 (6)	0.0356 (7)	0.0334 (8)	−0.0002 (5)	0.0151 (6)	−0.0101 (6)
C13	0.0256 (7)	0.0362 (7)	0.0356 (8)	−0.0118 (6)	0.0239 (6)	−0.0167 (6)
C14	0.0348 (8)	0.0266 (6)	0.0314 (8)	−0.0086 (5)	0.0256 (7)	−0.0073 (6)
C15	0.0245 (6)	0.0217 (6)	0.0259 (7)	−0.0012 (5)	0.0176 (6)	−0.0033 (5)

O1—C7	1.3470 (15)	C6—C7	1.4764 (16)
O1—C8	1.4582 (14)	C8—C9	1.485 (2)
O2—C7	1.2165 (13)	C8—H8A	0.9700
O3—N2	1.2325 (12)	C8—H8B	0.9700
O4—N2	1.2415 (13)	C9—H9A	0.9600
N1—C3	1.3518 (14)	C9—H9B	0.9600
N1—C10	1.4293 (14)	C9—H9C	0.9600
N1—H1N1	0.858 (17)	C10—C15	1.3852 (17)
N2—C2	1.4468 (15)	C10—C11	1.3904 (17)
C1—C6	1.3789 (17)	C11—C12	1.3875 (17)
C1—C2	1.3923 (15)	C11—H11A	0.9300
C1—H1A	0.9300	C12—C13	1.384 (2)
C2—C3	1.4262 (15)	C12—H12A	0.9300
C3—C4	1.4218 (16)	C13—C14	1.388 (2)
C4—C5	1.3727 (16)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.3935 (17)
C5—C6	1.4071 (15)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300
C7—O1—C8	115.13 (9)	O1—C8—H8A	110.2
C3—N1—C10	124.35 (10)	C9—C8—H8A	110.2
C3—N1—H1N1	117.8 (11)	O1—C8—H8B	110.2
C10—N1—H1N1	117.8 (11)	C9—C8—H8B	110.2
O3—N2—O4	122.02 (11)	H8A—C8—H8B	108.5
O3—N2—C2	118.75 (10)	C8—C9—H9A	109.5
O4—N2—C2	119.23 (9)	C8—C9—H9B	109.5
C6—C1—C2	121.06 (10)	H9A—C9—H9B	109.5
C6—C1—H1A	119.5	C8—C9—H9C	109.5
C2—C1—H1A	119.5	H9A—C9—H9C	109.5
C1—C2—C3	121.55 (11)	H9B—C9—H9C	109.5
C1—C2—N2	116.46 (10)	C15—C10—C11	120.29 (11)
C3—C2—N2	121.97 (10)	C15—C10—N1	121.04 (11)
N1—C3—C4	120.59 (10)	C11—C10—N1	118.58 (11)
N1—C3—C2	123.68 (11)	C12—C11—C10	120.00 (13)
C4—C3—C2	115.72 (10)	C12—C11—H11A	120.0
C5—C4—C3	122.11 (10)	C10—C11—H11A	120.0
C5—C4—H4A	118.9	C13—C12—C11	120.03 (13)
C3—C4—H4A	118.9	C13—C12—H12A	120.0
C4—C5—C6	120.86 (11)	C11—C12—H12A	120.0
C4—C5—H5A	119.6	C12—C13—C14	119.90 (11)
C6—C5—H5A	119.6	C12—C13—H13A	120.0
C1—C6—C5	118.69 (10)	C14—C13—H13A	120.0
C1—C6—C7	117.78 (10)	C13—C14—C15	120.36 (13)
C5—C6—C7	123.53 (11)	C13—C14—H14A	119.8
O2—C7—O1	122.94 (11)	C15—C14—H14A	119.8
O2—C7—C6	124.18 (11)	C10—C15—C14	119.41 (12)
O1—C7—C6	112.88 (9)	C10—C15—H15A	120.3
O1—C8—C9	107.49 (10)	C14—C15—H15A	120.3
C6—C1—C2—C3	−0.58 (18)	C4—C5—C6—C7	−179.04 (11)
C6—C1—C2—N2	177.85 (11)	C8—O1—C7—O2	−2.29 (17)
O3—N2—C2—C1	−7.34 (16)	C8—O1—C7—C6	177.49 (10)
O4—N2—C2—C1	173.15 (11)	C1—C6—C7—O2	−5.67 (18)
O3—N2—C2—C3	171.07 (11)	C5—C6—C7—O2	174.66 (12)
O4—N2—C2—C3	−8.44 (17)	C1—C6—C7—O1	174.56 (10)
C10—N1—C3—C4	3.33 (18)	C5—C6—C7—O1	−5.11 (17)
C10—N1—C3—C2	−177.07 (11)	C7—O1—C8—C9	−171.43 (11)
C1—C2—C3—N1	−178.51 (11)	C3—N1—C10—C15	72.36 (17)
N2—C2—C3—N1	3.15 (18)	C3—N1—C10—C11	−110.92 (14)
C1—C2—C3—C4	1.12 (17)	C15—C10—C11—C12	−0.1 (2)
N2—C2—C3—C4	−177.22 (10)	N1—C10—C11—C12	−176.86 (12)
N1—C3—C4—C5	179.17 (12)	C10—C11—C12—C13	−0.6 (2)
C2—C3—C4—C5	−0.47 (17)	C11—C12—C13—C14	0.9 (2)
C3—C4—C5—C6	−0.72 (19)	C12—C13—C14—C15	−0.5 (2)
C2—C1—C6—C5	−0.65 (18)	C11—C10—C15—C14	0.49 (19)
C2—C1—C6—C7	179.67 (11)	N1—C10—C15—C14	177.15 (12)
C4—C5—C6—C1	1.29 (18)	C13—C14—C15—C10	−0.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O4	0.859 (18)	2.00 (2)	2.6375 (17)	130.6 (17)
N1—H1N1···O2i	0.858 (17)	2.288 (16)	2.9411 (14)	133.0 (14)
C15—H15A···O2ii	0.93	2.45	3.342 (2)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O4	0.859 (18)	2.00 (2)	2.6375 (17)	130.6 (17)
N1—H1N1⋯O2i	0.858 (17)	2.288 (16)	2.9411 (14)	133.0 (14)
C15—H15A⋯O2ii	0.93	2.45	3.342 (2)	160

Symmetry codes: (i) ; (ii) .