Literature DB >> 21578956

2-Hydr-oxy-5-nitro-benzamide.

Abdul Rauf Raza, M Nawaz Tahir, Bushra Nisar, Mohammad Danish, Mohammad S Iqbal.

Abstract

In the title compound, C(7)H(6)N(2)O(4), an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds occur. Weak C-H⋯O links consolidate the packing, leading to R(2) (1)(7) and R(2) (2)(10) loops within (100) polymeric sheets.

Entities: Chemical Disease Species

Year: 2009 PMID： 21578956 PMCID： PMC2971888 DOI： 10.1107/S1600536809050119

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

Related literature

For related structures, see: Pertlik (1990 ▶); Raza et al. (2009 ▶).

Experimental

Crystal data

C7H6N2O4 M = 182.14 Monoclinic, a = 5.1803 (3) Å b = 11.1037 (8) Å c = 13.7214 (10) Å β = 100.642 (4)° V = 775.69 (9) Å3 Z = 4 Mo Kα radiation μ = 0.13 mm−1 T = 296 K 0.28 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.976 4581 measured reflections 1799 independent reflections 1434 reflections with I > 2σ(I) R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.037 wR(F 2) = 0.112 S = 1.05 1799 reflections 125 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.23 e Å−3 Δρmin = −0.21 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: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050119/hb5244sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050119/hb5244Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₇H₆N₂O₄	F(000) = 376
M_r = 182.14	D_x = 1.560 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1799 reflections
a = 5.1803 (3) Å	θ = 2.4–27.8°
b = 11.1037 (8) Å	µ = 0.13 mm⁻¹
c = 13.7214 (10) Å	T = 296 K
β = 100.642 (4)°	Prisms, light yellow
V = 775.69 (9) Å³	0.28 × 0.20 × 0.18 mm
Z = 4

Bruker Kappa APEXII CCD diffractometer	1799 independent reflections
Radiation source: fine-focus sealed tube	1434 reflections with I > 2σ(I)
graphite	R_int = 0.018
Detector resolution: 7.50 pixels mm^-1	θ_max = 27.8°, θ_min = 2.4°
ω scans	h = −6→6
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −14→13
T_min = 0.970, T_max = 0.976	l = −17→16
4581 measured reflections

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0629P)² + 0.0918P] where P = (F_o² + 2F_c²)/3
1799 reflections	(Δ/σ)_max < 0.001
125 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	U_iso*/U_eq
O1	0.5646 (2)	0.40418 (9)	0.31899 (9)	0.0527 (4)
O2	0.2337 (2)	0.46688 (9)	0.42269 (9)	0.0538 (4)
O3	0.1375 (2)	−0.09501 (9)	0.42368 (9)	0.0604 (4)
O4	0.4447 (2)	−0.15349 (9)	0.34804 (9)	0.0599 (4)
N1	0.0539 (3)	0.33482 (11)	0.51407 (10)	0.0505 (4)
N2	0.3188 (2)	−0.07405 (10)	0.37931 (8)	0.0425 (4)
C1	0.3227 (2)	0.26057 (11)	0.39880 (9)	0.0352 (3)
C2	0.5024 (3)	0.28970 (12)	0.33611 (10)	0.0393 (4)
C3	0.6220 (3)	0.19813 (14)	0.28969 (11)	0.0460 (4)
C4	0.5642 (3)	0.07915 (13)	0.30371 (10)	0.0427 (4)
C5	0.3840 (2)	0.05179 (11)	0.36410 (9)	0.0363 (4)
C6	0.2636 (2)	0.13973 (11)	0.41112 (9)	0.0351 (3)
C7	0.1992 (3)	0.36003 (11)	0.44683 (10)	0.0390 (4)
H1	0.48184	0.44981	0.34877	0.0632*
H1A	−0.032 (4)	0.3969 (16)	0.5380 (14)	0.0606*
H1B	0.028 (3)	0.2603 (18)	0.5307 (13)	0.0606*
H3	0.74118	0.21799	0.24920	0.0552*
H4	0.64399	0.01822	0.27341	0.0513*
H6	0.14354	0.11839	0.45083	0.0421*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0632 (7)	0.0386 (5)	0.0644 (7)	−0.0088 (5)	0.0331 (5)	0.0035 (5)
O2	0.0678 (7)	0.0286 (5)	0.0737 (7)	0.0004 (4)	0.0362 (5)	0.0027 (4)
O3	0.0834 (8)	0.0346 (5)	0.0760 (8)	−0.0045 (5)	0.0481 (6)	0.0018 (5)
O4	0.0723 (7)	0.0372 (6)	0.0751 (8)	0.0129 (5)	0.0267 (6)	−0.0080 (5)
N1	0.0732 (8)	0.0274 (6)	0.0610 (8)	0.0076 (5)	0.0389 (7)	0.0020 (5)
N2	0.0535 (7)	0.0333 (6)	0.0433 (6)	0.0050 (5)	0.0156 (5)	−0.0021 (4)
C1	0.0383 (6)	0.0321 (6)	0.0378 (6)	0.0010 (5)	0.0135 (5)	0.0011 (5)
C2	0.0412 (6)	0.0381 (7)	0.0411 (7)	−0.0044 (5)	0.0143 (5)	0.0029 (5)
C3	0.0454 (7)	0.0500 (8)	0.0490 (8)	−0.0033 (6)	0.0254 (6)	−0.0015 (6)
C4	0.0435 (7)	0.0433 (7)	0.0458 (7)	0.0044 (5)	0.0199 (5)	−0.0056 (5)
C5	0.0407 (6)	0.0315 (6)	0.0389 (7)	0.0024 (5)	0.0133 (5)	−0.0015 (5)
C6	0.0390 (6)	0.0319 (6)	0.0382 (6)	0.0023 (5)	0.0170 (5)	0.0007 (5)
C7	0.0451 (7)	0.0298 (6)	0.0452 (7)	0.0008 (5)	0.0161 (5)	0.0002 (5)

O1—C2	1.3427 (17)	C1—C2	1.4167 (19)
O2—C7	1.2535 (16)	C1—C6	1.3935 (17)
O3—N2	1.2321 (15)	C2—C3	1.403 (2)
O4—N2	1.2210 (15)	C3—C4	1.376 (2)
O1—H1	0.8200	C4—C5	1.3914 (19)
N1—C7	1.324 (2)	C5—C6	1.3811 (17)
N2—C5	1.4615 (16)	C3—H3	0.9300
N1—H1A	0.914 (19)	C4—H4	0.9300
N1—H1B	0.88 (2)	C6—H6	0.9300
C1—C7	1.4896 (18)

C2—O1—H1	109.00	C3—C4—C5	118.70 (13)
O3—N2—C5	117.94 (10)	N2—C5—C4	119.47 (11)
O4—N2—C5	119.21 (10)	N2—C5—C6	118.23 (10)
O3—N2—O4	122.86 (11)	C4—C5—C6	122.30 (12)
C7—N1—H1A	117.9 (12)	C1—C6—C5	119.72 (10)
C7—N1—H1B	121.1 (11)	O2—C7—C1	119.41 (13)
H1A—N1—H1B	120.8 (16)	N1—C7—C1	119.83 (11)
C6—C1—C7	122.57 (11)	O2—C7—N1	120.76 (13)
C2—C1—C6	118.51 (11)	C2—C3—H3	120.00
C2—C1—C7	118.91 (11)	C4—C3—H3	120.00
O1—C2—C3	117.79 (13)	C3—C4—H4	121.00
C1—C2—C3	120.33 (12)	C5—C4—H4	121.00
O1—C2—C1	121.89 (12)	C1—C6—H6	120.00
C2—C3—C4	120.43 (14)	C5—C6—H6	120.00

O3—N2—C5—C4	−171.90 (12)	C2—C1—C7—N1	−172.50 (13)
O3—N2—C5—C6	8.36 (17)	C6—C1—C7—O2	−170.64 (13)
O4—N2—C5—C4	8.18 (18)	C6—C1—C7—N1	9.1 (2)
O4—N2—C5—C6	−171.57 (12)	O1—C2—C3—C4	−179.42 (14)
C6—C1—C2—O1	178.56 (12)	C1—C2—C3—C4	0.7 (2)
C6—C1—C2—C3	−1.51 (19)	C2—C3—C4—C5	0.4 (2)
C7—C1—C2—O1	0.12 (19)	C3—C4—C5—N2	179.58 (12)
C7—C1—C2—C3	−179.95 (15)	C3—C4—C5—C6	−0.7 (2)
C2—C1—C6—C5	1.28 (17)	N2—C5—C6—C1	179.54 (11)
C7—C1—C6—C5	179.66 (12)	C4—C5—C6—C1	−0.20 (18)
C2—C1—C7—O2	7.73 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.82	1.79	2.5196 (16)	148
N1—H1A···O2ⁱ	0.914 (19)	1.969 (19)	2.8807 (17)	174.9 (18)
N1—H1B···O3ⁱⁱ	0.88 (2)	2.167 (19)	3.0193 (17)	164.6 (15)
C4—H4···O1ⁱⁱⁱ	0.93	2.49	3.3915 (18)	164
C6—H6···O3ⁱⁱ	0.93	2.47	3.3826 (16)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2	0.82	1.79	2.5196 (16)	148
N1—H1A⋯O2ⁱ	0.914 (19)	1.969 (19)	2.8807 (17)	174.9 (18)
N1—H1B⋯O3ⁱⁱ	0.88 (2)	2.167 (19)	3.0193 (17)	164.6 (15)
C4—H4⋯O1ⁱⁱⁱ	0.93	2.49	3.3915 (18)	164
C6—H6⋯O3ⁱⁱ	0.93	2.47	3.3826 (16)	169

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

3 in total

1 in total

1. 2-Hy-droxy-5-nitro-N-phenyl-benzamide.

Authors: Abdul Rauf Raza; Bushra Nisar; M Nawaz Tahir
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2010-06-26