N-(4-Bromo-phen-yl)-3,5-dinitro-benzamide.

The title mol-ecule, C(13)H(8)BrN(3)O(5), is slightly twisted, with the dihedral angle between the two benzene rings being 5.9 (1)°. In the crystal, N-H⋯O hydrogen bonds link the mol-ecules into one-dimensional chains running along [101]. Further stabilization of the crystal structure is provided by π-π inter-actions [shortest centroid-centroid distance = 3.6467 (17) Å].

Related literature

For background to the biological activity of N-substituted benzamides, their use in synthesis and for related structures, see: Saeed et al. (2011a ▶,b ▶).

Experimental

Crystal data

C13H8BrN3O5

M = 366.13

Monoclinic,

a = 7.1273 (2) Å

b = 26.6676 (7) Å

c = 7.5428 (2) Å

β = 101.652 (2)°

V = 1404.10 (7) Å3

Z = 4

Mo Kα radiation

μ = 2.96 mm−1

T = 296 K

0.56 × 0.34 × 0.30 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.288, T max = 0.471

18250 measured reflections

2476 independent reflections

2007 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.108

S = 1.10

2476 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.25 e Å−3

Δρmin = −0.46 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) I, global. DOI: 10.1107/S1600536811051464/tk5029sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051464/tk5029Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811051464/tk5029Isup3.cml

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

C13H8BrN3O5	F(000) = 728
Mr = 366.13	Dx = 1.732 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 18250 reflections
a = 7.1273 (2) Å	θ = 2.9–25.0°
b = 26.6676 (7) Å	µ = 2.96 mm−1
c = 7.5428 (2) Å	T = 296 K
β = 101.652 (2)°	Block, colourless
V = 1404.10 (7) Å3	0.56 × 0.34 × 0.30 mm
Z = 4

Bruker APEXII CCD diffractometer	2476 independent reflections
Radiation source: fine-focus sealed tube	2007 reflections with I > 2σ(I)
graphite	Rint = 0.060
ω and φ scan	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.288, Tmax = 0.471	k = −31→31
18250 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)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108	w = 1/[σ2(Fo2) + (0.0472P)2 + 0.9282P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
2476 reflections	Δρmax = 0.25 e Å−3
204 parameters	Δρmin = −0.46 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: 0.0074 (12)

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
Br1	0.80856 (6)	0.046874 (16)	0.25109 (7)	0.0884 (2)
O1	0.6333 (3)	0.28369 (8)	0.5032 (3)	0.0569 (6)
O2	0.9867 (5)	0.31665 (12)	1.3107 (3)	0.0879 (9)
O3	0.9761 (6)	0.39563 (13)	1.3387 (4)	0.1162 (14)
O4	0.8205 (5)	0.50043 (9)	0.8040 (5)	0.0986 (10)
O5	0.7279 (6)	0.46522 (10)	0.5447 (5)	0.0967 (11)
N1	0.8777 (3)	0.24105 (8)	0.6787 (3)	0.0395 (6)
N2	0.9563 (5)	0.35817 (13)	1.2475 (4)	0.0651 (9)
N3	0.7853 (5)	0.46389 (11)	0.7070 (6)	0.0655 (9)
C1	0.7638 (4)	0.28096 (10)	0.6368 (4)	0.0393 (6)
C2	0.8027 (3)	0.32503 (10)	0.7622 (4)	0.0341 (6)
C3	0.8632 (4)	0.32045 (10)	0.9473 (4)	0.0362 (6)
H3	0.8834	0.2890	1.0013	0.043*
C4	0.8932 (4)	0.36369 (11)	1.0508 (4)	0.0430 (7)
C5	0.8704 (4)	0.41094 (11)	0.9800 (4)	0.0487 (8)
H5	0.8934	0.4394	1.0524	0.058*
C6	0.8110 (4)	0.41394 (10)	0.7935 (5)	0.0456 (7)
C7	0.7736 (4)	0.37237 (10)	0.6849 (4)	0.0405 (6)
H7	0.7293	0.3759	0.5608	0.049*
C8	0.8647 (4)	0.19583 (10)	0.5760 (4)	0.0392 (6)
C9	0.8261 (4)	0.19669 (12)	0.3885 (4)	0.0488 (7)
H9	0.8107	0.2271	0.3268	0.059*
C10	0.8108 (5)	0.15204 (15)	0.2943 (5)	0.0580 (9)
H10	0.7828	0.1522	0.1685	0.070*
C11	0.8370 (4)	0.10718 (13)	0.3874 (5)	0.0576 (9)
C12	0.8826 (5)	0.10586 (12)	0.5729 (5)	0.0561 (8)
H12	0.9045	0.0754	0.6338	0.067*
C13	0.8955 (4)	0.15065 (11)	0.6683 (4)	0.0481 (8)
H13	0.9247	0.1504	0.7942	0.058*
H1N	0.958 (4)	0.2412 (10)	0.792 (4)	0.035 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.0662 (3)	0.0737 (3)	0.1252 (5)	−0.01117 (19)	0.0187 (3)	−0.0669 (3)
O1	0.0609 (13)	0.0435 (11)	0.0499 (13)	0.0067 (10)	−0.0278 (11)	−0.0061 (10)
O2	0.134 (3)	0.084 (2)	0.0409 (14)	−0.0258 (18)	0.0057 (15)	0.0037 (14)
O3	0.205 (4)	0.095 (2)	0.0539 (16)	−0.049 (2)	0.038 (2)	−0.0396 (17)
O4	0.105 (2)	0.0269 (13)	0.161 (3)	−0.0038 (13)	0.020 (2)	−0.0076 (16)
O5	0.133 (3)	0.0518 (16)	0.104 (3)	0.0173 (17)	0.022 (2)	0.0374 (16)
N1	0.0429 (13)	0.0309 (12)	0.0361 (13)	0.0010 (10)	−0.0123 (11)	−0.0037 (10)
N2	0.089 (2)	0.070 (2)	0.0407 (16)	−0.0319 (17)	0.0224 (15)	−0.0123 (15)
N3	0.0619 (19)	0.0326 (15)	0.104 (3)	0.0066 (13)	0.0229 (18)	0.0138 (16)
C1	0.0383 (15)	0.0335 (14)	0.0394 (15)	−0.0015 (11)	−0.0079 (12)	0.0023 (12)
C2	0.0309 (14)	0.0294 (13)	0.0381 (15)	0.0005 (10)	−0.0024 (11)	0.0013 (11)
C3	0.0344 (14)	0.0323 (13)	0.0394 (15)	−0.0027 (11)	0.0016 (11)	0.0020 (11)
C4	0.0448 (16)	0.0465 (16)	0.0389 (16)	−0.0090 (13)	0.0116 (13)	−0.0087 (13)
C5	0.0530 (18)	0.0356 (15)	0.060 (2)	−0.0102 (13)	0.0159 (15)	−0.0130 (14)
C6	0.0410 (16)	0.0261 (14)	0.071 (2)	0.0006 (11)	0.0144 (15)	0.0024 (13)
C7	0.0370 (15)	0.0359 (15)	0.0447 (16)	0.0038 (12)	−0.0012 (12)	0.0058 (13)
C8	0.0331 (14)	0.0350 (14)	0.0440 (16)	−0.0016 (11)	−0.0051 (11)	−0.0108 (12)
C9	0.0471 (17)	0.0522 (18)	0.0446 (18)	−0.0024 (14)	0.0035 (13)	−0.0088 (14)
C10	0.0495 (19)	0.075 (2)	0.0485 (19)	−0.0023 (16)	0.0085 (15)	−0.0248 (18)
C11	0.0373 (17)	0.057 (2)	0.077 (2)	−0.0065 (14)	0.0087 (16)	−0.0346 (18)
C12	0.0495 (19)	0.0402 (16)	0.075 (2)	−0.0007 (14)	0.0032 (16)	−0.0147 (16)
C13	0.0492 (17)	0.0358 (15)	0.0517 (18)	0.0011 (13)	−0.0077 (14)	−0.0076 (13)

Br1—C11	1.898 (3)	C4—C5	1.366 (4)
O1—C1	1.228 (3)	C5—C6	1.387 (5)
O2—N2	1.208 (4)	C5—H5	0.9300
O3—N2	1.205 (4)	C6—C7	1.372 (4)
O4—N3	1.214 (4)	C7—H7	0.9300
O5—N3	1.211 (5)	C8—C9	1.385 (4)
N1—C1	1.337 (4)	C8—C13	1.387 (4)
N1—C8	1.426 (3)	C9—C10	1.380 (5)
N1—H1N	0.93 (3)	C9—H9	0.9300
N2—C4	1.468 (4)	C10—C11	1.381 (5)
N3—C6	1.478 (4)	C10—H10	0.9300
C1—C2	1.499 (4)	C11—C12	1.371 (5)
C2—C3	1.381 (4)	C12—C13	1.388 (4)
C2—C7	1.388 (4)	C12—H12	0.9300
C3—C4	1.385 (4)	C13—H13	0.9300
C3—H3	0.9300
C1—N1—C8	125.1 (2)	C7—C6—C5	122.8 (3)
C1—N1—H1N	116.5 (17)	C7—C6—N3	118.2 (3)
C8—N1—H1N	117.7 (17)	C5—C6—N3	119.0 (3)
O3—N2—O2	123.0 (3)	C6—C7—C2	119.3 (3)
O3—N2—C4	118.1 (3)	C6—C7—H7	120.3
O2—N2—C4	119.0 (3)	C2—C7—H7	120.3
O5—N3—O4	124.9 (3)	C9—C8—C13	120.4 (3)
O5—N3—C6	117.3 (3)	C9—C8—N1	121.2 (3)
O4—N3—C6	117.7 (4)	C13—C8—N1	118.4 (3)
O1—C1—N1	124.4 (3)	C10—C9—C8	119.4 (3)
O1—C1—C2	118.9 (2)	C10—C9—H9	120.3
N1—C1—C2	116.7 (2)	C8—C9—H9	120.3
C3—C2—C7	119.6 (2)	C9—C10—C11	119.8 (3)
C3—C2—C1	123.3 (2)	C9—C10—H10	120.1
C7—C2—C1	117.1 (2)	C11—C10—H10	120.1
C2—C3—C4	118.5 (2)	C12—C11—C10	121.4 (3)
C2—C3—H3	120.7	C12—C11—Br1	120.6 (3)
C4—C3—H3	120.7	C10—C11—Br1	118.0 (3)
C5—C4—C3	123.7 (3)	C11—C12—C13	118.9 (3)
C5—C4—N2	118.4 (3)	C11—C12—H12	120.5
C3—C4—N2	117.8 (3)	C13—C12—H12	120.5
C4—C5—C6	116.0 (3)	C8—C13—C12	120.0 (3)
C4—C5—H5	122.0	C8—C13—H13	120.0
C6—C5—H5	122.0	C12—C13—H13	120.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.93 (3)	1.93 (3)	2.818 (3)	159 (3)

I	J	CgI···CgJ	Dihedral angle	CgI_Perp	CgJ_Perp
1	2i	3.7391 (17)	6.24 (14)	3.5945 (11)	-3.6827 (13)
1	2ii	3.6467 (17)	6.24 (14)	-3.5254 (12)	3.4038 (13)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.93 (3)	1.93 (3)	2.818 (3)	159 (3)

Symmetry code: (i) .