Ethyl 2-(3,5-dinitro-benzamido)-benzoate.

The title mol-ecule, C(16)H(13)N(3)O(7), is slightly twisted, with the dihedral angle between the two benzene ring planes being 17.4 (1)°. An intra-molecular N-H⋯O hydrogen bond is observed. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along the b axis.

Related literature

For background to the biological activity of N-substituted benzamides and their use in synthesis, see: Saeed et al. (2011a ▶,b ▶). For the structures of related chloro­phenyl­benzamides, see: Gowda et al. (2007a ▶,b ▶,c ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ortho-hydrogen steric hindrance, see: Karle & Brockway (1944 ▶).

Experimental

Crystal data

C16H13N3O7

M = 359.29

Monoclinic,

a = 12.4662 (4) Å

b = 17.7213 (5) Å

c = 7.4352 (2) Å

β = 96.658 (2)°

V = 1631.49 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.52 × 0.30 × 0.26 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.942, T max = 0.970

16092 measured reflections

2808 independent reflections

1961 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.174

S = 1.11

2808 reflections

237 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811053074/fk2047sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053074/fk2047Isup2.hkl

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

C16H13N3O7	F(000) = 744
Mr = 359.29	Dx = 1.463 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16092 reflections
a = 12.4662 (4) Å	θ = 2.8–25.0°
b = 17.7213 (5) Å	µ = 0.12 mm−1
c = 7.4352 (2) Å	T = 296 K
β = 96.658 (2)°	Block, colourless
V = 1631.49 (8) Å3	0.52 × 0.30 × 0.26 mm
Z = 4

Bruker APEXII CCD diffractometer	2808 independent reflections
Radiation source: fine-focus sealed tube	1961 reflections with I > 2σ(I)
graphite	Rint = 0.040
ω and φ scan	θmax = 25.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
Tmin = 0.942, Tmax = 0.970	k = −21→21
16092 measured reflections	l = −8→8

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.174	w = 1/[σ2(Fo2) + (0.0679P)2 + 0.9448P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
2808 reflections	Δρmax = 0.18 e Å−3
237 parameters	Δρmin = −0.22 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

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	0.66429 (15)	0.10807 (11)	0.9056 (3)	0.0724 (6)
O2	0.49758 (15)	0.11624 (11)	0.7638 (3)	0.0678 (6)
O3	0.29471 (18)	−0.10623 (12)	0.5275 (3)	0.0855 (7)
O4	−0.03437 (19)	−0.05325 (16)	0.1499 (3)	0.0870 (7)
O5	−0.11189 (19)	0.05489 (17)	0.1563 (4)	0.1005 (9)
O6	0.0466 (2)	0.24889 (16)	0.5560 (5)	0.1221 (11)
O7	0.19530 (19)	0.22737 (13)	0.7234 (4)	0.0908 (8)
N1	0.40070 (16)	−0.01091 (13)	0.6539 (3)	0.0560 (6)
H1	0.4020	0.0374	0.6654	0.067*
N2	−0.0365 (2)	0.01221 (19)	0.2005 (3)	0.0721 (7)
N3	0.1241 (2)	0.20962 (15)	0.6060 (4)	0.0752 (7)
C1	0.5738 (2)	0.07809 (15)	0.8276 (3)	0.0540 (6)
C2	0.57853 (19)	−0.00579 (14)	0.8223 (3)	0.0496 (6)
C3	0.6705 (2)	−0.04275 (16)	0.9032 (4)	0.0585 (7)
H3	0.7267	−0.0147	0.9634	0.070*
C4	0.6794 (2)	−0.12038 (17)	0.8952 (4)	0.0691 (8)
H4	0.7408	−0.1446	0.9502	0.083*
C5	0.5968 (3)	−0.16112 (17)	0.8055 (5)	0.0763 (9)
H5	0.6032	−0.2133	0.7988	0.092*
C6	0.5043 (2)	−0.12685 (16)	0.7246 (4)	0.0676 (8)
H6	0.4491	−0.1559	0.6648	0.081*
C7	0.4936 (2)	−0.04870 (15)	0.7326 (3)	0.0524 (6)
C8	0.3099 (2)	−0.03932 (16)	0.5632 (4)	0.0582 (7)
C9	0.22294 (19)	0.01719 (15)	0.5044 (3)	0.0518 (6)
C10	0.1393 (2)	−0.00719 (16)	0.3779 (3)	0.0560 (7)
H10	0.1405	−0.0555	0.3293	0.067*
C11	0.0544 (2)	0.04096 (18)	0.3248 (3)	0.0588 (7)
C12	0.0482 (2)	0.11277 (17)	0.3938 (4)	0.0627 (7)
H12	−0.0095	0.1446	0.3568	0.075*
C13	0.1312 (2)	0.13480 (15)	0.5197 (4)	0.0587 (7)
C14	0.2185 (2)	0.08975 (15)	0.5764 (4)	0.0545 (6)
H14	0.2736	0.1073	0.6611	0.065*
C15	0.6721 (3)	0.19029 (18)	0.9047 (6)	0.0866 (10)
H15A	0.6505	0.2096	0.7838	0.104*
H15B	0.6251	0.2119	0.9863	0.104*
C16	0.7843 (3)	0.2102 (2)	0.9632 (9)	0.139 (2)
H16A	0.7925	0.2640	0.9594	0.208*
H16B	0.8302	0.1870	0.8841	0.208*
H16C	0.8039	0.1926	1.0847	0.208*

	U11	U22	U33	U12	U13	U23
O1	0.0586 (11)	0.0578 (12)	0.0953 (15)	−0.0026 (9)	−0.0149 (10)	−0.0026 (10)
O2	0.0540 (11)	0.0594 (11)	0.0863 (14)	0.0043 (9)	−0.0075 (10)	0.0016 (10)
O3	0.0770 (14)	0.0613 (13)	0.1109 (18)	−0.0009 (11)	−0.0198 (13)	−0.0172 (12)
O4	0.0805 (15)	0.1026 (19)	0.0738 (15)	−0.0281 (14)	−0.0077 (11)	−0.0029 (13)
O5	0.0623 (14)	0.135 (2)	0.0963 (18)	0.0002 (14)	−0.0259 (13)	0.0126 (16)
O6	0.0978 (19)	0.101 (2)	0.158 (3)	0.0457 (16)	−0.0271 (18)	−0.0201 (18)
O7	0.0794 (15)	0.0655 (14)	0.122 (2)	−0.0015 (11)	−0.0130 (14)	−0.0100 (13)
N1	0.0480 (12)	0.0551 (12)	0.0622 (14)	0.0009 (9)	−0.0043 (10)	0.0008 (10)
N2	0.0546 (15)	0.105 (2)	0.0549 (14)	−0.0166 (15)	−0.0023 (11)	0.0122 (14)
N3	0.0634 (15)	0.0656 (15)	0.093 (2)	0.0088 (13)	−0.0045 (14)	0.0049 (14)
C1	0.0465 (14)	0.0586 (15)	0.0560 (15)	0.0011 (12)	0.0016 (11)	0.0001 (12)
C2	0.0458 (13)	0.0576 (15)	0.0452 (13)	0.0029 (11)	0.0045 (10)	0.0006 (11)
C3	0.0506 (15)	0.0693 (17)	0.0544 (15)	0.0061 (12)	0.0004 (11)	0.0038 (12)
C4	0.0638 (17)	0.0657 (18)	0.0753 (19)	0.0196 (14)	−0.0021 (15)	0.0069 (15)
C5	0.077 (2)	0.0551 (17)	0.094 (2)	0.0141 (15)	−0.0024 (17)	−0.0024 (16)
C6	0.0644 (17)	0.0556 (16)	0.080 (2)	0.0028 (13)	−0.0027 (14)	−0.0031 (14)
C7	0.0497 (14)	0.0573 (15)	0.0500 (14)	0.0061 (11)	0.0052 (11)	0.0035 (11)
C8	0.0514 (15)	0.0647 (17)	0.0573 (15)	−0.0025 (12)	0.0015 (12)	−0.0026 (13)
C9	0.0438 (13)	0.0612 (16)	0.0501 (14)	−0.0029 (11)	0.0038 (11)	0.0037 (12)
C10	0.0486 (14)	0.0701 (17)	0.0488 (14)	−0.0094 (12)	0.0034 (11)	0.0023 (12)
C11	0.0437 (14)	0.085 (2)	0.0463 (14)	−0.0120 (13)	0.0009 (11)	0.0105 (13)
C12	0.0464 (14)	0.0742 (19)	0.0664 (17)	0.0013 (13)	0.0016 (12)	0.0177 (15)
C13	0.0488 (14)	0.0588 (16)	0.0682 (17)	−0.0017 (12)	0.0053 (12)	0.0104 (13)
C14	0.0458 (13)	0.0598 (15)	0.0565 (15)	−0.0060 (11)	−0.0001 (11)	0.0051 (12)
C15	0.075 (2)	0.0586 (18)	0.121 (3)	−0.0012 (16)	−0.011 (2)	−0.0072 (18)
C16	0.086 (3)	0.075 (3)	0.243 (6)	−0.011 (2)	−0.036 (3)	−0.007 (3)

O1—C1	1.319 (3)	C5—C6	1.378 (4)
O1—C15	1.460 (4)	C5—H5	0.9300
O2—C1	1.217 (3)	C6—C7	1.393 (4)
O3—C8	1.225 (3)	C6—H6	0.9300
O4—N2	1.221 (4)	C8—C9	1.503 (4)
O5—N2	1.221 (4)	C9—C10	1.390 (4)
O6—N3	1.214 (3)	C9—C14	1.396 (4)
O7—N3	1.212 (3)	C10—C11	1.381 (4)
N1—C8	1.346 (3)	C10—H10	0.9300
N1—C7	1.405 (3)	C11—C12	1.378 (4)
N1—H1	0.8600	C12—C13	1.370 (4)
N2—C11	1.468 (3)	C12—H12	0.9300
N3—C13	1.480 (4)	C13—C14	1.376 (4)
C1—C2	1.488 (4)	C14—H14	0.9300
C2—C3	1.395 (3)	C15—C16	1.458 (5)
C2—C7	1.407 (4)	C15—H15A	0.9700
C3—C4	1.382 (4)	C15—H15B	0.9700
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.366 (4)	C16—H16B	0.9600
C4—H4	0.9300	C16—H16C	0.9600
C1—O1—C15	117.0 (2)	O3—C8—C9	119.6 (2)
C8—N1—C7	129.4 (2)	N1—C8—C9	115.6 (2)
C8—N1—H1	115.3	C10—C9—C14	119.1 (2)
C7—N1—H1	115.3	C10—C9—C8	116.7 (2)
O5—N2—O4	123.3 (3)	C14—C9—C8	124.1 (2)
O5—N2—C11	117.9 (3)	C11—C10—C9	119.4 (3)
O4—N2—C11	118.7 (3)	C11—C10—H10	120.3
O7—N3—O6	124.2 (3)	C9—C10—H10	120.3
O7—N3—C13	118.0 (2)	C12—C11—C10	122.6 (2)
O6—N3—C13	117.8 (3)	C12—C11—N2	118.8 (3)
O2—C1—O1	122.5 (2)	C10—C11—N2	118.4 (3)
O2—C1—C2	125.2 (2)	C13—C12—C11	116.6 (3)
O1—C1—C2	112.3 (2)	C13—C12—H12	121.7
C3—C2—C7	119.1 (2)	C11—C12—H12	121.7
C3—C2—C1	119.4 (2)	C12—C13—C14	123.5 (3)
C7—C2—C1	121.5 (2)	C12—C13—N3	118.2 (2)
C4—C3—C2	121.0 (3)	C14—C13—N3	118.2 (2)
C4—C3—H3	119.5	C13—C14—C9	118.8 (2)
C2—C3—H3	119.5	C13—C14—H14	120.6
C5—C4—C3	119.2 (3)	C9—C14—H14	120.6
C5—C4—H4	120.4	C16—C15—O1	107.6 (3)
C3—C4—H4	120.4	C16—C15—H15A	110.2
C4—C5—C6	121.7 (3)	O1—C15—H15A	110.2
C4—C5—H5	119.2	C16—C15—H15B	110.2
C6—C5—H5	119.2	O1—C15—H15B	110.2
C5—C6—C7	119.9 (3)	H15A—C15—H15B	108.5
C5—C6—H6	120.0	C15—C16—H16A	109.5
C7—C6—H6	120.0	C15—C16—H16B	109.5
C6—C7—C2	119.1 (2)	H16A—C16—H16B	109.5
C6—C7—N1	122.3 (2)	C15—C16—H16C	109.5
C2—C7—N1	118.6 (2)	H16A—C16—H16C	109.5
O3—C8—N1	124.8 (3)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.92	2.641 (3)	140.
C16—H16A···O3i	0.96	2.55	3.402 (4)	148

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.86	1.92	2.641 (3)	140
C16—H16A⋯O3i	0.96	2.55	3.402 (4)	148

Symmetry code: (i) .