Ethyl 4-anilino-3-nitrobenzoate.

In the title compound, C(15)H(14)N(2)O(4), the aromatic rings are oriented at a dihedral angle of 78.33 (3)°. An intra-molecular N-H⋯O hydrogen bond results in a non-planar six-membered ring with a flattened-boat conformation. In the crystal structure, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules. π-π contacts between the phenyl rings and both the phenyl and benzene rings, [centroid-centroid distances = 3.841 (3) and 3.961 (3) Å] may further stabilize the structure.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H14N2O4

M = 286.28

Monoclinic,

a = 10.683 (2) Å

b = 9.905 (2) Å

c = 13.698 (3) Å

β = 105.05 (3)°

V = 1399.7 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 294 (2) K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf-Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.971, T max = 0.980

2647 measured reflections

2508 independent reflections

1519 reflections with I > 2σ(I)

R int = 0.051

3 standard reflections frequency: 120 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.199

S = 1.00

2508 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808041329/hk2595sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041329/hk2595Isup2.hkl

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

C15H14N2O4	F(000) = 600
Mr = 286.28	Dx = 1.358 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 10.683 (2) Å	θ = 10–13°
b = 9.905 (2) Å	µ = 0.10 mm−1
c = 13.698 (3) Å	T = 294 K
β = 105.05 (3)°	Block, colorless
V = 1399.7 (5) Å3	0.30 × 0.20 × 0.20 mm
Z = 4

Enraf-Nonius CAD-4 diffractometer	1519 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
graphite	θmax = 25.2°, θmin = 2.2°
ω/2θ scans	h = −12→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.971, Tmax = 0.980	l = 0→16
2647 measured reflections	3 standard reflections every 120 min
2508 independent reflections	intensity decay: none

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.199	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.050P)2 + 3.4P] where P = (Fo2 + 2Fc2)/3
2508 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.32 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.

Refinement. Refinement of F2 against ALL refle (Sheldrick, 2008)ctions. 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	0.0229 (3)	0.1219 (3)	0.2353 (2)	0.0602 (9)
O2	0.1935 (2)	−0.0076 (3)	0.2291 (2)	0.0605 (8)
O3	−0.0506 (3)	−0.4222 (3)	−0.1083 (3)	0.0705 (10)
O4	0.1353 (3)	−0.3433 (4)	−0.0297 (3)	0.0852 (12)
N1	0.0155 (3)	−0.3404 (4)	−0.0480 (3)	0.0560 (9)
N2	−0.2640 (3)	−0.2968 (4)	−0.1003 (2)	0.0523 (9)
H2A	−0.2321	−0.3625	−0.1271	0.063*
C1	0.0290 (5)	0.2946 (6)	0.3560 (4)	0.0943 (19)
H1A	0.0836	0.3471	0.4092	0.141*
H1B	−0.0328	0.2455	0.3820	0.141*
H1C	−0.0159	0.3535	0.3027	0.141*
C2	0.1084 (4)	0.1999 (5)	0.3166 (4)	0.0683 (14)
H2B	0.1541	0.1399	0.3700	0.082*
H2C	0.1718	0.2486	0.2909	0.082*
C3	0.0774 (4)	0.0183 (4)	0.2003 (3)	0.0489 (10)
C4	−0.0131 (3)	−0.0606 (4)	0.1202 (3)	0.0464 (10)
C5	0.0350 (3)	−0.1607 (4)	0.0723 (3)	0.0452 (10)
H5A	0.1238	−0.1764	0.0897	0.054*
C6	−0.0450 (3)	−0.2399 (4)	−0.0018 (3)	0.0434 (9)
C7	−0.1821 (3)	−0.2191 (4)	−0.0295 (3)	0.0438 (9)
C8	−0.2275 (3)	−0.1155 (4)	0.0203 (3)	0.0486 (10)
H8A	−0.3161	−0.0984	0.0034	0.058*
C9	−0.1479 (3)	−0.0370 (4)	0.0934 (3)	0.0465 (10)
H9A	−0.1827	0.0313	0.1249	0.056*
C10	−0.4030 (3)	−0.2732 (5)	−0.1322 (3)	0.0526 (11)
C11	−0.4831 (4)	−0.3588 (6)	−0.1004 (4)	0.0754 (15)
H11A	−0.4487	−0.4284	−0.0559	0.090*
C12	−0.6166 (5)	−0.3428 (7)	−0.1342 (5)	0.0907 (19)
H12A	−0.6722	−0.4012	−0.1127	0.109*
C13	−0.6650 (4)	−0.2397 (7)	−0.1995 (5)	0.096 (2)
H13A	−0.7543	−0.2280	−0.2219	0.115*
C14	−0.5848 (4)	−0.1536 (6)	−0.2324 (4)	0.0854 (18)
H14A	−0.6199	−0.0841	−0.2768	0.103*
C15	−0.4501 (4)	−0.1691 (5)	−0.1999 (4)	0.0654 (13)
H15B	−0.3944	−0.1122	−0.2226	0.078*

	U11	U22	U33	U12	U13	U23
O1	0.0423 (16)	0.0602 (19)	0.0576 (18)	−0.0073 (14)	−0.0236 (13)	−0.0105 (15)
O2	0.0306 (14)	0.075 (2)	0.0604 (18)	−0.0033 (14)	−0.0167 (12)	0.0023 (16)
O3	0.0482 (17)	0.067 (2)	0.080 (2)	0.0093 (16)	−0.0131 (16)	−0.0220 (18)
O4	0.0283 (15)	0.115 (3)	0.104 (3)	0.0123 (17)	0.0021 (16)	−0.016 (2)
N1	0.0367 (18)	0.069 (2)	0.056 (2)	0.0118 (18)	−0.0003 (16)	−0.0016 (19)
N2	0.0263 (16)	0.066 (2)	0.056 (2)	−0.0001 (15)	−0.0046 (14)	−0.0167 (18)
C1	0.090 (4)	0.092 (4)	0.082 (4)	−0.013 (3)	−0.013 (3)	−0.026 (3)
C2	0.057 (3)	0.068 (3)	0.061 (3)	−0.013 (2)	−0.018 (2)	−0.017 (3)
C3	0.040 (2)	0.053 (3)	0.042 (2)	−0.0083 (19)	−0.0115 (17)	0.009 (2)
C4	0.0278 (18)	0.052 (2)	0.045 (2)	−0.0041 (17)	−0.0165 (16)	0.0055 (19)
C5	0.0262 (18)	0.052 (2)	0.046 (2)	−0.0026 (17)	−0.0117 (16)	0.0101 (19)
C6	0.0299 (18)	0.053 (2)	0.041 (2)	0.0049 (17)	−0.0023 (16)	0.0030 (18)
C7	0.0240 (17)	0.049 (2)	0.048 (2)	−0.0009 (17)	−0.0090 (15)	−0.0001 (19)
C8	0.0233 (17)	0.060 (3)	0.053 (2)	0.0000 (17)	−0.0071 (16)	−0.001 (2)
C9	0.0327 (19)	0.052 (2)	0.047 (2)	−0.0006 (17)	−0.0021 (16)	−0.0051 (19)
C10	0.0226 (18)	0.068 (3)	0.057 (3)	−0.0039 (19)	−0.0082 (17)	−0.023 (2)
C11	0.047 (3)	0.107 (4)	0.072 (3)	−0.015 (3)	0.014 (2)	−0.016 (3)
C12	0.048 (3)	0.118 (5)	0.114 (5)	−0.026 (3)	0.036 (3)	−0.033 (4)
C13	0.024 (2)	0.127 (6)	0.122 (5)	−0.009 (3)	−0.006 (3)	−0.064 (5)
C14	0.039 (3)	0.098 (4)	0.097 (4)	0.016 (3)	−0.022 (3)	−0.030 (3)
C15	0.033 (2)	0.059 (3)	0.089 (3)	0.002 (2)	−0.013 (2)	−0.008 (3)

O1—C2	1.463 (5)	C5—C6	1.387 (5)
O1—C3	1.329 (5)	C5—H5A	0.9300
O2—C3	1.227 (4)	C6—C7	1.429 (5)
N1—O3	1.239 (4)	C7—C8	1.387 (5)
N1—O4	1.240 (4)	C8—C9	1.374 (5)
N1—C6	1.422 (5)	C8—H8A	0.9300
N2—C7	1.363 (5)	C9—H9A	0.9300
N2—C10	1.454 (4)	C10—C11	1.354 (6)
N2—H2A	0.8600	C10—C15	1.390 (6)
C1—C2	1.458 (7)	C11—C12	1.390 (7)
C1—H1A	0.9600	C11—H11A	0.9300
C1—H1B	0.9600	C12—C13	1.367 (9)
C1—H1C	0.9600	C12—H12A	0.9300
C2—H2B	0.9700	C13—C14	1.366 (8)
C2—H2C	0.9700	C13—H13A	0.9300
C3—C4	1.483 (5)	C14—C15	1.400 (6)
C4—C5	1.360 (6)	C14—H14A	0.9300
C4—C9	1.410 (5)	C15—H15B	0.9300
C3—O1—C2	115.9 (3)	C5—C6—N1	117.2 (3)
O3—N1—O4	120.0 (4)	C5—C6—C7	120.5 (4)
O3—N1—C6	120.6 (3)	N2—C7—C8	121.7 (3)
O4—N1—C6	119.4 (4)	N2—C7—C6	122.1 (4)
C7—N2—C10	122.7 (3)	C8—C7—C6	116.1 (3)
C7—N2—H2A	118.7	C7—C8—H8A	118.4
C10—N2—H2A	118.7	C9—C8—C7	123.2 (3)
C2—C1—H1A	109.5	C9—C8—H8A	118.4
C2—C1—H1B	109.5	C4—C9—H9A	120.3
C2—C1—H1C	109.5	C8—C9—C4	119.5 (4)
H1A—C1—H1B	109.5	C8—C9—H9A	120.3
H1A—C1—H1C	109.5	C11—C10—C15	122.0 (4)
H1B—C1—H1C	109.5	C11—C10—N2	118.9 (4)
O1—C2—H2B	110.0	C15—C10—N2	119.0 (4)
O1—C2—H2C	110.0	C10—C11—C12	120.1 (6)
C1—C2—O1	108.3 (4)	C10—C11—H11A	120.0
C1—C2—H2B	110.0	C12—C11—H11A	120.0
C1—C2—H2C	110.0	C11—C12—H12A	120.5
H2B—C2—H2C	108.4	C13—C12—C11	118.9 (5)
O1—C3—C4	114.3 (3)	C13—C12—H12A	120.5
O2—C3—O1	123.1 (4)	C12—C13—H13A	119.4
O2—C3—C4	122.6 (4)	C14—C13—C12	121.3 (5)
C5—C4—C9	118.9 (3)	C14—C13—H13A	119.4
C5—C4—C3	119.0 (3)	C13—C14—C15	120.5 (6)
C9—C4—C3	122.1 (4)	C13—C14—H14A	119.8
C4—C5—C6	121.8 (3)	C15—C14—H14A	119.8
C4—C5—H5A	119.1	C10—C15—C14	117.2 (5)
C6—C5—H5A	119.1	C10—C15—H15B	121.4
N1—C6—C7	122.4 (3)	C14—C15—H15B	121.4
C3—O1—C2—C1	−171.2 (4)	N1—C6—C7—N2	1.8 (6)
C2—O1—C3—O2	−4.1 (6)	C5—C6—C7—C8	1.1 (6)
C2—O1—C3—C4	178.3 (4)	N1—C6—C7—C8	−178.6 (4)
O2—C3—C4—C5	−3.9 (6)	N2—C7—C8—C9	178.7 (4)
O1—C3—C4—C5	173.7 (4)	C6—C7—C8—C9	−0.9 (6)
O2—C3—C4—C9	174.8 (4)	C7—C8—C9—C4	0.1 (6)
O1—C3—C4—C9	−7.6 (5)	C5—C4—C9—C8	0.4 (6)
C9—C4—C5—C6	−0.2 (6)	C3—C4—C9—C8	−178.4 (4)
C3—C4—C5—C6	178.6 (4)	C7—N2—C10—C11	−106.2 (5)
C4—C5—C6—N1	179.1 (4)	C7—N2—C10—C15	78.1 (5)
C4—C5—C6—C7	−0.6 (6)	C15—C10—C11—C12	−1.0 (7)
O3—N1—C6—C5	173.7 (4)	N2—C10—C11—C12	−176.6 (4)
O4—N1—C6—C5	−8.2 (6)	C10—C11—C12—C13	−0.1 (8)
O3—N1—C6—C7	−6.6 (6)	C11—C12—C13—C14	0.5 (9)
O4—N1—C6—C7	171.5 (4)	C12—C13—C14—C15	0.1 (8)
C10—N2—C7—C8	3.1 (6)	C11—C10—C15—C14	1.6 (7)
C10—N2—C7—C6	−177.4 (4)	N2—C10—C15—C14	177.2 (4)
C5—C6—C7—N2	−178.5 (4)	C13—C14—C15—C10	−1.1 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3	0.86	1.98	2.623 (5)	131
N2—H2A···O2i	0.86	2.31	2.978 (4)	134

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3	0.86	1.98	2.623 (5)	131
N2—H2A⋯O2i	0.86	2.31	2.978 (4)	134

Symmetry code: (i) .