Literature DB >> 22606167

4-Bromo-N-(4-meth-oxy-2-nitro-phen-yl)benzamide.

Weerawat Sripet, Suchada Chantrapromma, Pumsak Ruanwas, Hoong-Kun Fun.

Abstract

In the title compound, C(14)H(11)BrN(2)O(4), the amide segment makes dihedral angles of 23.4 (2) and 20.5 (2)° with the benzene rings, while the dihedral angle between the bezene rings is 2.90 (8)°. The nitro and meth-oxy groups are almost coplanar with their bound benzene ring, with the r.m.s. deviation for the 11 non-H atoms being 0.0265 (1) Å. An intra-molecular N-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked into [2-10] chains by weak C-H⋯O and C-H⋯Br inter-actions, which form an R(2) (2)(8) motif between pairs of mol-ecules in the chain. A Br⋯O [3.2018 (12) Å] short contact also occurs.

Entities: Chemical Disease Species

Year: 2012 PMID： 22606167 PMCID： PMC3344164 DOI： 10.1107/S1600536812010963

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Johnston & Taylor (2011 ▶); Li & Cui (2011 ▶); Saeed et al. (2008) ▶. For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H11BrN2O4 M = 351.15 Triclinic, a = 6.1219 (2) Å b = 7.6519 (3) Å c = 14.3504 (6) Å α = 89.197 (1)° β = 84.795 (1)° γ = 77.983 (1)° V = 654.78 (4) Å3 Z = 2 Mo Kα radiation μ = 3.16 mm−1 T = 100 K 0.54 × 0.27 × 0.17 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.281, T max = 0.616 14195 measured reflections 3725 independent reflections 3558 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.026 wR(F 2) = 0.080 S = 1.12 3725 reflections 195 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.93 e Å−3 Δρmin = −0.48 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/S1600536812010963/hb6654sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010963/hb6654Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812010963/hb6654Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₄H₁₁BrN₂O₄	Z = 2
M_r = 351.15	F(000) = 352
Triclinic, P1	D_x = 1.781 Mg m⁻³
Hall symbol: -P 1	Melting point = 434–436 K
a = 6.1219 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.6519 (3) Å	Cell parameters from 3725 reflections
c = 14.3504 (6) Å	θ = 2.9–30.0°
α = 89.197 (1)°	µ = 3.16 mm⁻¹
β = 84.795 (1)°	T = 100 K
γ = 77.983 (1)°	Block, orange
V = 654.78 (4) Å³	0.54 × 0.27 × 0.17 mm

Bruker APEX DUO CCD area-detector diffractometer	3725 independent reflections
Radiation source: sealed tube	3558 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 30.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→8
T_min = 0.281, T_max = 0.616	k = −10→10
14195 measured reflections	l = −20→20

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ²(F_o²) + (0.0525P)² + 0.2246P] where P = (F_o² + 2F_c²)/3
3725 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.93 e Å⁻³
0 restraints	Δρ_min = −0.48 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	U_iso*/U_eq
Br1	−0.43080 (2)	1.27590 (2)	0.081247 (10)	0.02080 (7)
O1	0.2430 (2)	0.77009 (18)	0.38411 (9)	0.0252 (3)
O4	1.2328 (2)	0.25761 (17)	0.36805 (9)	0.0225 (2)
O3	1.0773 (2)	0.5836 (2)	0.08860 (9)	0.0292 (3)
O2	0.7257 (2)	0.70628 (18)	0.09318 (9)	0.0240 (3)
N1	0.4593 (2)	0.69155 (19)	0.24641 (10)	0.0182 (3)
N2	0.8886 (2)	0.61497 (18)	0.12882 (9)	0.0183 (3)
C2	−0.1093 (3)	0.9574 (2)	0.28387 (11)	0.0183 (3)
H2A	−0.1492	0.9142	0.3441	0.022*
C3	−0.2720 (3)	1.0681 (2)	0.23633 (11)	0.0181 (3)
H3A	−0.4229	1.0997	0.2629	0.022*
C4	−0.2085 (3)	1.1314 (2)	0.14887 (11)	0.0165 (3)
C5	0.0114 (3)	1.0909 (2)	0.10918 (11)	0.0178 (3)
H5A	0.0518	1.1394	0.0504	0.021*
C6	0.1719 (3)	0.9777 (2)	0.15721 (11)	0.0179 (3)
H6A	0.3227	0.9473	0.1305	0.021*
C1	0.1126 (3)	0.9086 (2)	0.24441 (11)	0.0163 (3)
C7	0.2764 (3)	0.7849 (2)	0.29928 (11)	0.0176 (3)
C8	0.6493 (3)	0.5785 (2)	0.27797 (11)	0.0164 (3)
C9	0.8567 (3)	0.5414 (2)	0.22300 (10)	0.0166 (3)
C10	1.0464 (3)	0.4333 (2)	0.25465 (11)	0.0175 (3)
H10A	1.1836	0.4113	0.2159	0.021*
C11	1.0359 (3)	0.3573 (2)	0.34300 (11)	0.0173 (3)
C12	0.8314 (3)	0.3867 (2)	0.39815 (11)	0.0187 (3)
H12A	0.8215	0.3326	0.4579	0.022*
C13	0.6427 (3)	0.4951 (2)	0.36556 (11)	0.0184 (3)
H13A	0.5048	0.5132	0.4038	0.022*
C14	1.2322 (3)	0.1852 (2)	0.46014 (13)	0.0249 (3)
H14A	1.3862	0.1315	0.4731	0.037*
H14B	1.1412	0.0937	0.4650	0.037*
H14C	1.1689	0.2807	0.5057	0.037*
H1N1	0.467 (4)	0.710 (4)	0.1886 (19)	0.028 (6)*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.01483 (10)	0.02630 (10)	0.01952 (10)	−0.00065 (6)	−0.00143 (6)	0.00490 (6)
O1	0.0244 (6)	0.0295 (6)	0.0164 (5)	0.0048 (5)	0.0024 (4)	0.0015 (5)
O4	0.0157 (6)	0.0283 (6)	0.0209 (6)	0.0013 (4)	−0.0021 (4)	0.0057 (4)
O3	0.0174 (6)	0.0415 (7)	0.0236 (6)	0.0013 (5)	0.0065 (5)	0.0085 (5)
O2	0.0190 (6)	0.0306 (6)	0.0189 (5)	0.0019 (5)	0.0001 (4)	0.0063 (5)
N1	0.0159 (6)	0.0215 (6)	0.0146 (6)	0.0012 (5)	0.0004 (5)	0.0015 (5)
N2	0.0187 (7)	0.0196 (6)	0.0156 (6)	−0.0027 (5)	0.0005 (5)	0.0015 (5)
C2	0.0176 (7)	0.0208 (7)	0.0153 (6)	−0.0020 (5)	0.0009 (5)	0.0004 (5)
C3	0.0138 (7)	0.0211 (7)	0.0180 (7)	−0.0015 (5)	0.0016 (5)	0.0001 (5)
C4	0.0136 (7)	0.0180 (6)	0.0171 (7)	−0.0012 (5)	−0.0011 (5)	0.0004 (5)
C5	0.0156 (7)	0.0196 (7)	0.0168 (7)	−0.0017 (5)	0.0018 (5)	0.0012 (5)
C6	0.0146 (7)	0.0195 (6)	0.0180 (7)	−0.0015 (5)	0.0020 (5)	0.0007 (5)
C1	0.0147 (7)	0.0165 (6)	0.0163 (6)	−0.0010 (5)	−0.0001 (5)	−0.0001 (5)
C7	0.0157 (7)	0.0172 (6)	0.0184 (7)	−0.0008 (5)	0.0002 (5)	0.0001 (5)
C8	0.0142 (7)	0.0174 (6)	0.0166 (6)	−0.0009 (5)	−0.0012 (5)	0.0000 (5)
C9	0.0172 (7)	0.0177 (6)	0.0142 (6)	−0.0032 (5)	0.0007 (5)	0.0009 (5)
C10	0.0142 (7)	0.0190 (6)	0.0185 (7)	−0.0025 (5)	0.0010 (5)	−0.0001 (5)
C11	0.0140 (7)	0.0182 (6)	0.0192 (7)	−0.0016 (5)	−0.0027 (5)	0.0005 (5)
C12	0.0191 (7)	0.0196 (6)	0.0160 (7)	−0.0016 (5)	−0.0002 (5)	0.0024 (5)
C13	0.0152 (7)	0.0208 (7)	0.0174 (7)	−0.0012 (5)	0.0013 (5)	0.0012 (5)
C14	0.0237 (9)	0.0254 (8)	0.0233 (8)	0.0014 (6)	−0.0053 (6)	0.0037 (6)

Br1—C4	1.8975 (16)	C5—H5A	0.9500
O1—C7	1.224 (2)	C6—C1	1.399 (2)
O4—C11	1.3615 (19)	C6—H6A	0.9500
O4—C14	1.426 (2)	C1—C7	1.499 (2)
O3—N2	1.2220 (19)	C8—C13	1.403 (2)
O2—N2	1.2395 (19)	C8—C9	1.410 (2)
N1—C7	1.367 (2)	C9—C10	1.387 (2)
N1—C8	1.404 (2)	C10—C11	1.389 (2)
N1—H1N1	0.84 (3)	C10—H10A	0.9500
N2—C9	1.4692 (19)	C11—C12	1.397 (2)
C2—C3	1.390 (2)	C12—C13	1.389 (2)
C2—C1	1.400 (2)	C12—H12A	0.9500
C2—H2A	0.9500	C13—H13A	0.9500
C3—C4	1.391 (2)	C14—H14A	0.9800
C3—H3A	0.9500	C14—H14B	0.9800
C4—C5	1.387 (2)	C14—H14C	0.9800
C5—C6	1.394 (2)

C11—O4—C14	117.04 (13)	O1—C7—C1	121.42 (14)
C7—N1—C8	127.66 (14)	N1—C7—C1	114.35 (13)
C7—N1—H1N1	117.3 (19)	C13—C8—N1	121.83 (14)
C8—N1—H1N1	114.8 (19)	C13—C8—C9	116.34 (14)
O3—N2—O2	122.41 (14)	N1—C8—C9	121.82 (14)
O3—N2—C9	118.06 (14)	C10—C9—C8	122.13 (14)
O2—N2—C9	119.53 (13)	C10—C9—N2	115.12 (13)
C3—C2—C1	121.01 (14)	C8—C9—N2	122.75 (14)
C3—C2—H2A	119.5	C9—C10—C11	120.04 (14)
C1—C2—H2A	119.5	C9—C10—H10A	120.0
C2—C3—C4	118.32 (14)	C11—C10—H10A	120.0
C2—C3—H3A	120.8	O4—C11—C10	115.23 (14)
C4—C3—H3A	120.8	O4—C11—C12	125.42 (14)
C5—C4—C3	122.18 (15)	C10—C11—C12	119.35 (14)
C5—C4—Br1	119.02 (11)	C13—C12—C11	119.98 (14)
C3—C4—Br1	118.80 (12)	C13—C12—H12A	120.0
C4—C5—C6	118.73 (14)	C11—C12—H12A	120.0
C4—C5—H5A	120.6	C12—C13—C8	122.10 (14)
C6—C5—H5A	120.6	C12—C13—H13A	119.0
C5—C6—C1	120.52 (14)	C8—C13—H13A	119.0
C5—C6—H6A	119.7	O4—C14—H14A	109.5
C1—C6—H6A	119.7	O4—C14—H14B	109.5
C6—C1—C2	119.17 (14)	H14A—C14—H14B	109.5
C6—C1—C7	123.21 (14)	O4—C14—H14C	109.5
C2—C1—C7	117.61 (13)	H14A—C14—H14C	109.5
O1—C7—N1	124.23 (15)	H14B—C14—H14C	109.5

C1—C2—C3—C4	−0.9 (2)	N1—C8—C9—C10	178.41 (14)
C2—C3—C4—C5	−1.5 (2)	C13—C8—C9—N2	178.41 (14)
C2—C3—C4—Br1	177.86 (12)	N1—C8—C9—N2	−1.0 (2)
C3—C4—C5—C6	2.4 (2)	O3—N2—C9—C10	−3.6 (2)
Br1—C4—C5—C6	−176.97 (12)	O2—N2—C9—C10	176.71 (14)
C4—C5—C6—C1	−0.9 (2)	O3—N2—C9—C8	175.88 (15)
C5—C6—C1—C2	−1.3 (2)	O2—N2—C9—C8	−3.8 (2)
C5—C6—C1—C7	179.40 (14)	C8—C9—C10—C11	0.2 (2)
C3—C2—C1—C6	2.2 (2)	N2—C9—C10—C11	179.64 (14)
C3—C2—C1—C7	−178.44 (14)	C14—O4—C11—C10	176.68 (14)
C8—N1—C7—O1	−6.9 (3)	C14—O4—C11—C12	−3.5 (2)
C8—N1—C7—C1	173.95 (14)	C9—C10—C11—O4	−178.33 (14)
C6—C1—C7—O1	157.07 (16)	C9—C10—C11—C12	1.8 (2)
C2—C1—C7—O1	−22.2 (2)	O4—C11—C12—C13	178.40 (15)
C6—C1—C7—N1	−23.7 (2)	C10—C11—C12—C13	−1.8 (2)
C2—C1—C7—N1	156.97 (15)	C11—C12—C13—C8	−0.3 (2)
C7—N1—C8—C13	23.9 (2)	N1—C8—C13—C12	−178.36 (15)
C7—N1—C8—C9	−156.70 (16)	C9—C8—C13—C12	2.2 (2)
C13—C8—C9—C10	−2.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2	0.84 (3)	1.99 (3)	2.6318 (19)	132 (2)
C3—H3A···O4ⁱ	0.95	2.57	3.475 (2)	160
C12—H12A···O1ⁱⁱ	0.95	2.41	3.358 (2)	172
C10—H10A···Br1ⁱⁱⁱ	0.95	2.93	3.863 (2)	167

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2	0.84 (3)	1.99 (3)	2.6318 (19)	132 (2)
C3—H3A⋯O4ⁱ	0.95	2.57	3.475 (2)	160
C12—H12A⋯O1ⁱⁱ	0.95	2.41	3.358 (2)	172
C10—H10A⋯Br1ⁱⁱⁱ	0.95	2.93	3.863 (2)	167

Symmetry codes: (i) ; (ii) ; (iii) .

5 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. N-(2-Chloro-4-nitro-phen-yl)-2-nitro-benzamide.

Authors: Aamer Saeed; Shahid Hussain; Ulrich Flörke
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2008-03-12

3. N-(3,5-Dimeth-oxy-phen-yl)benzamide.

Authors: Hong-Lei Li; Jiang-Tao Cui
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-06-11

4. 4-Nitro-N-(3-nitro-phen-yl)benzamide.

Authors: Dean H Johnston; Colin R Taylor
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-09-30

5. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20