N-Methyl-3,5-dinitro-benzamide.

The asymmetric unit of the title compound, C(8)H(7)N(3)O(5), contains two independent mol-ecules in which the amide plane is oriented at dihedral angles of 29.82 (2) and 31.17 (2)° with respect to the benzene ring. In the crystal, mol-ecules are connected via inter-molecular N-H⋯O hydrogen bonds, forming chains running along the b axis.

Related literature

For general background to the biological activity of benzamide derivatives, see: Lee et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H7N3O5

M = 225.16

Orthorhombic,

a = 10.716 (2) Å

b = 10.057 (2) Å

c = 36.101 (7) Å

V = 3890.6 (13) Å3

Z = 16

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.962, T max = 0.987

4711 measured reflections

3402 independent reflections

1653 reflections with I > 2σ(I)

R int = 0.0582

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.162

S = 0.96

3402 reflections

289 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811053888/xu5409sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811053888/xu5409Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811053888/xu5409Isup3.cml

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

C8H7N3O5	F(000) = 1856
Mr = 225.16	Dx = 1.538 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25 reflections
a = 10.716 (2) Å	θ = 9–13°
b = 10.057 (2) Å	µ = 0.13 mm−1
c = 36.101 (7) Å	T = 293 K
V = 3890.6 (13) Å3	Block, yellow
Z = 16	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1653 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.058
graphite	θmax = 25.1°, θmin = 2.2°
ω/2θ scans	h = 0→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→11
Tmin = 0.962, Tmax = 0.987	l = 0→42
4711 measured reflections	3 standard reflections every 200 reflections
3402 independent reflections	intensity decay: 1%

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 0.96	w = 1/[σ2(Fo2) + (0.0619P)2] where P = (Fo2 + 2Fc2)/3
3402 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 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 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
N1	1.1588 (3)	0.7222 (4)	0.65015 (10)	0.0554 (9)
C1	0.9707 (3)	0.8426 (4)	0.67035 (11)	0.0444 (10)
H1A	0.9221	0.7795	0.6582	0.053*
O1	1.0927 (3)	0.6404 (3)	0.63547 (10)	0.0798 (11)
O2	1.2734 (2)	0.7187 (3)	0.64960 (8)	0.0716 (9)
C2	1.0989 (3)	0.8326 (4)	0.67030 (11)	0.0462 (10)
N2	1.1949 (4)	1.1247 (4)	0.72609 (10)	0.0571 (10)
N3	0.7009 (3)	0.8718 (3)	0.68582 (10)	0.0568 (10)
H3A	0.7314	0.7927	0.6850	0.068*
O3	1.3077 (3)	1.1073 (3)	0.72618 (9)	0.0726 (10)
C3	1.1751 (3)	0.9227 (4)	0.68860 (12)	0.0521 (11)
H3B	1.2616	0.9148	0.6885	0.063*
O4	1.1423 (3)	1.2198 (3)	0.74015 (10)	0.0745 (10)
C4	1.1155 (3)	1.0243 (4)	0.70688 (12)	0.0461 (10)
O5	0.7395 (2)	1.0907 (2)	0.68914 (9)	0.0636 (9)
C5	0.9889 (3)	1.0400 (4)	0.70711 (11)	0.0437 (10)
H5A	0.9527	1.1114	0.7194	0.052*
C6	0.9151 (3)	0.9481 (3)	0.68874 (10)	0.0413 (10)
C7	0.7776 (3)	0.9749 (4)	0.68801 (11)	0.0445 (10)
C8	0.5670 (3)	0.8895 (4)	0.68472 (14)	0.0705 (14)
H8A	0.5272	0.8042	0.6832	0.106*
H8B	0.5450	0.9416	0.6634	0.106*
H8C	0.5401	0.9344	0.7068	0.106*
O6	0.3317 (3)	0.2716 (3)	0.39302 (10)	0.0788 (11)
O7	0.1844 (3)	0.1345 (4)	0.40663 (10)	0.0918 (12)
O8	0.2726 (3)	−0.2445 (4)	0.48397 (10)	0.0938 (12)
O9	0.4620 (4)	−0.2891 (4)	0.49911 (11)	0.0952 (12)
O10	0.7598 (2)	0.1750 (2)	0.42863 (8)	0.0614 (9)
N4	0.2939 (3)	0.1676 (4)	0.40662 (11)	0.0617 (11)
N5	0.3840 (4)	−0.2228 (4)	0.48302 (11)	0.0669 (11)
N6	0.8109 (3)	−0.0414 (3)	0.43239 (9)	0.0503 (10)
H6A	0.7843	−0.1212	0.4356	0.060*
C9	0.5097 (3)	0.1061 (4)	0.42133 (11)	0.0452 (10)
H9A	0.5364	0.1806	0.4083	0.054*
C10	0.3841 (3)	0.0788 (4)	0.42467 (12)	0.0501 (11)
C11	0.3408 (4)	−0.0288 (4)	0.44465 (12)	0.0560 (11)
H11A	0.2558	−0.0460	0.4469	0.067*
C12	0.4279 (3)	−0.1087 (4)	0.46088 (11)	0.0481 (10)
C13	0.5549 (3)	−0.0875 (3)	0.45744 (11)	0.0468 (10)
H13A	0.6116	−0.1457	0.4683	0.056*
C14	0.5960 (3)	0.0213 (3)	0.43772 (11)	0.0390 (9)
C15	0.7307 (3)	0.0574 (3)	0.43282 (11)	0.0435 (10)
C16	0.9431 (3)	−0.0190 (4)	0.42662 (15)	0.0718 (14)
H16A	0.9863	−0.1025	0.4270	0.108*
H16B	0.9748	0.0372	0.4460	0.108*
H16C	0.9557	0.0234	0.4031	0.108*

	U11	U22	U33	U12	U13	U23
N1	0.063 (2)	0.052 (2)	0.051 (3)	0.010 (2)	0.003 (2)	−0.001 (2)
C1	0.046 (2)	0.039 (2)	0.048 (3)	−0.0017 (18)	−0.004 (2)	−0.002 (2)
O1	0.082 (2)	0.064 (2)	0.093 (3)	−0.0010 (18)	0.012 (2)	−0.035 (2)
O2	0.0549 (19)	0.091 (2)	0.069 (2)	0.0238 (17)	0.0071 (17)	−0.0031 (19)
C2	0.052 (2)	0.038 (2)	0.049 (3)	0.0070 (19)	0.003 (2)	−0.001 (2)
N2	0.058 (2)	0.057 (2)	0.056 (3)	−0.012 (2)	−0.010 (2)	0.000 (2)
N3	0.0419 (17)	0.0308 (16)	0.098 (3)	−0.0009 (15)	−0.0010 (18)	0.007 (2)
O3	0.0486 (17)	0.091 (2)	0.078 (2)	−0.0116 (17)	−0.0149 (17)	0.003 (2)
C3	0.043 (2)	0.052 (2)	0.061 (3)	0.005 (2)	−0.003 (2)	0.009 (2)
O4	0.077 (2)	0.0621 (19)	0.085 (3)	−0.0036 (18)	−0.0174 (18)	−0.021 (2)
C4	0.042 (2)	0.042 (2)	0.055 (3)	−0.0048 (19)	−0.004 (2)	0.002 (2)
O5	0.0520 (16)	0.0334 (15)	0.106 (3)	0.0035 (13)	−0.0022 (17)	−0.0014 (15)
C5	0.048 (2)	0.040 (2)	0.043 (2)	−0.0008 (19)	0.0021 (19)	0.001 (2)
C6	0.042 (2)	0.034 (2)	0.048 (3)	0.0019 (18)	0.000 (2)	0.004 (2)
C7	0.054 (2)	0.031 (2)	0.049 (3)	0.001 (2)	0.001 (2)	0.001 (2)
C8	0.045 (2)	0.051 (2)	0.116 (4)	−0.001 (2)	0.000 (3)	0.002 (3)
O6	0.068 (2)	0.066 (2)	0.102 (3)	0.0145 (19)	−0.019 (2)	0.010 (2)
O7	0.0410 (17)	0.129 (3)	0.106 (3)	−0.0026 (19)	−0.0210 (18)	0.015 (2)
O8	0.072 (2)	0.117 (3)	0.092 (3)	−0.041 (2)	0.016 (2)	0.019 (2)
O9	0.099 (3)	0.079 (3)	0.108 (3)	−0.009 (2)	0.016 (2)	0.032 (2)
O10	0.0528 (16)	0.0324 (14)	0.099 (2)	−0.0012 (13)	0.0006 (17)	0.0076 (16)
N4	0.046 (2)	0.075 (3)	0.064 (3)	0.010 (2)	−0.016 (2)	−0.014 (2)
N5	0.073 (3)	0.069 (3)	0.058 (3)	−0.020 (2)	0.014 (2)	0.000 (2)
N6	0.0394 (17)	0.0264 (16)	0.085 (3)	−0.0011 (14)	0.0063 (17)	0.0019 (18)
C9	0.046 (2)	0.035 (2)	0.055 (3)	−0.0028 (18)	0.000 (2)	−0.003 (2)
C10	0.046 (2)	0.049 (2)	0.056 (3)	0.003 (2)	−0.008 (2)	−0.014 (2)
C11	0.051 (2)	0.061 (3)	0.055 (3)	−0.007 (2)	0.005 (2)	−0.009 (2)
C12	0.053 (2)	0.044 (2)	0.047 (3)	−0.010 (2)	0.009 (2)	0.001 (2)
C13	0.055 (2)	0.037 (2)	0.049 (3)	−0.0001 (19)	0.002 (2)	−0.004 (2)
C14	0.040 (2)	0.0296 (18)	0.047 (2)	0.0027 (17)	−0.0007 (18)	−0.0053 (19)
C15	0.048 (2)	0.027 (2)	0.056 (3)	−0.0007 (18)	−0.003 (2)	−0.0014 (19)
C16	0.045 (2)	0.049 (2)	0.121 (4)	−0.002 (2)	0.007 (3)	0.016 (3)

N1—O1	1.207 (4)	O6—N4	1.224 (4)
N1—O2	1.229 (4)	O7—N4	1.221 (4)
N1—C2	1.475 (5)	O8—N5	1.214 (4)
C1—C2	1.378 (5)	O9—N5	1.217 (4)
C1—C6	1.386 (5)	O10—C15	1.232 (4)
C1—H1A	0.9300	N4—C10	1.468 (5)
C2—C3	1.387 (5)	N5—C12	1.475 (5)
N2—O4	1.221 (4)	N6—C15	1.314 (4)
N2—O3	1.221 (4)	N6—C16	1.449 (4)
N2—C4	1.491 (5)	N6—H6A	0.8600
N3—C7	1.325 (4)	C9—C10	1.379 (5)
N3—C8	1.446 (4)	C9—C14	1.391 (5)
N3—H3A	0.8600	C9—H9A	0.9300
C3—C4	1.374 (5)	C10—C11	1.381 (5)
C3—H3B	0.9300	C11—C12	1.364 (5)
C4—C5	1.366 (5)	C11—H11A	0.9300
O5—C7	1.234 (4)	C12—C13	1.383 (5)
C5—C6	1.385 (5)	C13—C14	1.378 (5)
C5—H5A	0.9300	C13—H13A	0.9300
C6—C7	1.498 (5)	C14—C15	1.498 (5)
C8—H8A	0.9600	C16—H16A	0.9600
C8—H8B	0.9600	C16—H16B	0.9600
C8—H8C	0.9600	C16—H16C	0.9600
O1—N1—O2	124.0 (4)	O7—N4—O6	123.5 (4)
O1—N1—C2	118.3 (3)	O7—N4—C10	117.8 (4)
O2—N1—C2	117.6 (4)	O6—N4—C10	118.7 (3)
C2—C1—C6	119.0 (3)	O8—N5—O9	124.3 (4)
C2—C1—H1A	120.5	O8—N5—C12	118.0 (4)
C6—C1—H1A	120.5	O9—N5—C12	117.7 (4)
C1—C2—C3	122.6 (4)	C15—N6—C16	121.6 (3)
C1—C2—N1	119.3 (4)	C15—N6—H6A	119.2
C3—C2—N1	118.1 (3)	C16—N6—H6A	119.2
O4—N2—O3	124.6 (4)	C10—C9—C14	119.4 (4)
O4—N2—C4	117.4 (3)	C10—C9—H9A	120.3
O3—N2—C4	118.0 (4)	C14—C9—H9A	120.3
C7—N3—C8	121.3 (3)	C9—C10—C11	122.0 (4)
C7—N3—H3A	119.3	C9—C10—N4	118.8 (4)
C8—N3—H3A	119.3	C11—C10—N4	119.2 (4)
C4—C3—C2	116.2 (3)	C12—C11—C10	117.1 (4)
C4—C3—H3B	121.9	C12—C11—H11A	121.4
C2—C3—H3B	121.9	C10—C11—H11A	121.4
C5—C4—C3	123.4 (4)	C11—C12—C13	122.9 (4)
C5—C4—N2	119.1 (4)	C11—C12—N5	118.2 (4)
C3—C4—N2	117.5 (3)	C13—C12—N5	118.9 (4)
C4—C5—C6	119.2 (4)	C14—C13—C12	119.0 (4)
C4—C5—H5A	120.4	C14—C13—H13A	120.5
C6—C5—H5A	120.4	C12—C13—H13A	120.5
C5—C6—C1	119.6 (3)	C13—C14—C9	119.6 (3)
C5—C6—C7	116.7 (3)	C13—C14—C15	124.2 (3)
C1—C6—C7	123.5 (3)	C9—C14—C15	116.2 (3)
O5—C7—N3	122.4 (3)	O10—C15—N6	123.9 (3)
O5—C7—C6	119.6 (3)	O10—C15—C14	119.4 (3)
N3—C7—C6	118.0 (3)	N6—C15—C14	116.6 (3)
N3—C8—H8A	109.5	N6—C16—H16A	109.5
N3—C8—H8B	109.5	N6—C16—H16B	109.5
H8A—C8—H8B	109.5	H16A—C16—H16B	109.5
N3—C8—H8C	109.5	N6—C16—H16C	109.5
H8A—C8—H8C	109.5	H16A—C16—H16C	109.5
H8B—C8—H8C	109.5	H16B—C16—H16C	109.5
C6—C1—C2—C3	1.3 (6)	C14—C9—C10—C11	1.7 (6)
C6—C1—C2—N1	−178.8 (3)	C14—C9—C10—N4	−178.8 (3)
O1—N1—C2—C1	−2.9 (6)	O7—N4—C10—C9	172.6 (4)
O2—N1—C2—C1	177.6 (4)	O6—N4—C10—C9	−8.7 (6)
O1—N1—C2—C3	177.0 (4)	O7—N4—C10—C11	−7.8 (6)
O2—N1—C2—C3	−2.5 (5)	O6—N4—C10—C11	170.8 (4)
C1—C2—C3—C4	−0.4 (6)	C9—C10—C11—C12	−0.6 (6)
N1—C2—C3—C4	179.7 (3)	N4—C10—C11—C12	179.9 (4)
C2—C3—C4—C5	−1.0 (6)	C10—C11—C12—C13	−1.3 (6)
C2—C3—C4—N2	−178.6 (3)	C10—C11—C12—N5	178.8 (4)
O4—N2—C4—C5	−2.6 (6)	O8—N5—C12—C11	4.2 (6)
O3—N2—C4—C5	178.6 (4)	O9—N5—C12—C11	−175.9 (4)
O4—N2—C4—C3	175.1 (4)	O8—N5—C12—C13	−175.8 (4)
O3—N2—C4—C3	−3.8 (6)	O9—N5—C12—C13	4.1 (6)
C3—C4—C5—C6	1.4 (6)	C11—C12—C13—C14	2.0 (6)
N2—C4—C5—C6	178.9 (3)	N5—C12—C13—C14	−178.1 (3)
C4—C5—C6—C1	−0.3 (5)	C12—C13—C14—C9	−0.8 (5)
C4—C5—C6—C7	−176.4 (3)	C12—C13—C14—C15	178.3 (4)
C2—C1—C6—C5	−1.0 (5)	C10—C9—C14—C13	−0.9 (6)
C2—C1—C6—C7	174.8 (4)	C10—C9—C14—C15	179.9 (3)
C8—N3—C7—O5	−0.2 (7)	C16—N6—C15—O10	−0.3 (7)
C8—N3—C7—C6	−179.6 (4)	C16—N6—C15—C14	177.9 (3)
C5—C6—C7—O5	29.1 (5)	C13—C14—C15—O10	−151.0 (4)
C1—C6—C7—O5	−146.9 (4)	C9—C14—C15—O10	28.1 (5)
C5—C6—C7—N3	−151.5 (4)	C13—C14—C15—N6	30.6 (6)
C1—C6—C7—N3	32.5 (6)	C9—C14—C15—N6	−150.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5i	0.86	2.06	2.900 (4)	165.
N6—H6A···O10i	0.86	2.12	2.955 (4)	164.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5i	0.86	2.06	2.900 (4)	165
N6—H6A⋯O10i	0.86	2.12	2.955 (4)	164

Symmetry code: (i) .