Literature DB >> 21588050

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

Abdul Rauf Raza, Bushra Nisar, M Nawaz Tahir.   

Abstract

The mol-ecule of the title compound, C(13)H(10)N(2)O(4), is almost planar with a dihedral angle between the benzene rings of 1.99 (13)°. The nitro group and its parent benzene ring are oriented at a dihedral angle of 7.6 (3)°. Intra-molecular C-H⋯O and N-H⋯O hydrogen bonds form two planar S(6) motifs. Inter-molecular O-H⋯O=C hydrogen bonds join mol-ecules into chains extending along the c axis.

Entities:  

Year:  2010        PMID： 21588050      PMCID： PMC3007066          DOI： 10.1107/S1600536810024621

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


Related literature

For similar structures, see: Raza et al. (2009a ▶,b ▶). For graph-set notation of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H10N2O4 M = 258.23 Monoclinic, a = 9.9012 (2) Å b = 4.7821 (1) Å c = 12.3369 (4) Å β = 97.919 (1)° V = 578.56 (3) Å3 Z = 2 Mo Kα radiation μ = 0.11 mm−1 T = 296 K 0.34 × 0.12 × 0.10 mm

Data collection

Bruker Kappa APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.979, T max = 0.988 4381 measured reflections 1042 independent reflections 966 reflections with I > 2σ(I) R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.029 wR(F 2) = 0.071 S = 1.06 1042 reflections 173 parameters 2 restraints H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.13 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 for Windows (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/S1600536810024621/gk2288sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024621/gk2288Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H10N2O4F(000) = 268
Mr = 258.23Dx = 1.482 Mg m−3
Monoclinic, PcMo Kα radiation, λ = 0.71073 Å
Hall symbol: P -2ycCell parameters from 931 reflections
a = 9.9012 (2) Åθ = 2.8–26.0°
b = 4.7821 (1) ŵ = 0.11 mm−1
c = 12.3369 (4) ÅT = 296 K
β = 97.919 (1)°Needle, colorless
V = 578.56 (3) Å30.34 × 0.12 × 0.10 mm
Z = 2
Bruker Kappa APEXII CCD diffractometer1042 independent reflections
Radiation source: fine-focus sealed tube966 reflections with I > 2σ(I)
graphiteRint = 0.022
Detector resolution: 8.20 pixels mm-1θmax = 25.3°, θmin = 3.7°
ω scansh = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −5→5
Tmin = 0.979, Tmax = 0.988l = −14→14
4381 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.071H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.0447P)2 + 0.0284P] where P = (Fo2 + 2Fc2)/3
1042 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.13 e Å−3
2 restraintsΔρmin = −0.13 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 esds 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.
xyzUiso*/Ueq
O10.87642 (17)0.9971 (4)−0.04316 (13)0.0503 (6)
O21.3304 (2)1.6021 (5)0.27212 (18)0.0782 (8)
O31.2680 (2)1.2889 (5)0.38093 (16)0.0688 (8)
O40.88497 (17)0.7133 (3)0.27868 (13)0.0484 (5)
N11.25998 (19)1.4015 (5)0.29149 (17)0.0502 (7)
N20.78477 (17)0.6615 (4)0.10417 (14)0.0398 (6)
C10.9697 (2)1.0963 (5)0.03785 (17)0.0374 (7)
C21.0633 (2)1.2998 (5)0.01674 (19)0.0452 (8)
C31.1591 (2)1.4007 (5)0.09772 (19)0.0440 (8)
C41.1606 (2)1.2957 (5)0.20283 (19)0.0395 (7)
C51.0696 (2)1.0964 (5)0.22608 (17)0.0382 (7)
C60.9712 (2)0.9923 (4)0.14475 (17)0.0353 (7)
C70.8756 (2)0.7790 (4)0.18042 (17)0.0356 (6)
C80.6844 (2)0.4564 (4)0.11679 (19)0.0378 (7)
C90.6723 (3)0.3201 (5)0.2141 (2)0.0467 (8)
C100.5716 (3)0.1191 (5)0.2159 (2)0.0562 (9)
C110.4843 (3)0.0530 (5)0.1231 (3)0.0565 (9)
C120.4959 (2)0.1904 (5)0.0268 (2)0.0563 (9)
C130.5957 (3)0.3893 (5)0.0230 (2)0.0494 (8)
H10.882281.08314−0.099820.0754*
H21.060611.36856−0.054040.0542*
H2A0.787310.717550.038240.0477*
H31.221491.535930.082840.0528*
H51.073511.029730.297270.0459*
H90.730900.363010.277440.0561*
H100.563220.027350.281110.0674*
H110.41778−0.083470.125370.0677*
H120.435980.14877−0.035970.0675*
H130.603790.47916−0.042610.0592*
U11U22U33U12U13U23
O10.0561 (9)0.0674 (11)0.0251 (9)−0.0152 (8)−0.0027 (7)0.0045 (8)
O20.0822 (13)0.0874 (15)0.0612 (13)−0.0397 (13)−0.0041 (10)−0.0068 (11)
O30.0754 (13)0.0863 (14)0.0391 (12)−0.0147 (11)−0.0117 (9)0.0010 (10)
O40.0645 (10)0.0525 (9)0.0267 (9)−0.0075 (8)0.0014 (7)0.0006 (7)
N10.0480 (11)0.0581 (13)0.0424 (13)−0.0011 (10)−0.0009 (9)−0.0086 (10)
N20.0470 (11)0.0462 (11)0.0258 (10)−0.0058 (8)0.0041 (8)0.0007 (8)
C10.0381 (11)0.0458 (12)0.0275 (12)0.0011 (10)0.0016 (8)−0.0024 (9)
C20.0503 (14)0.0554 (14)0.0301 (13)−0.0010 (11)0.0060 (10)0.0036 (10)
C30.0416 (12)0.0488 (14)0.0419 (14)−0.0062 (10)0.0067 (10)−0.0030 (11)
C40.0372 (11)0.0447 (12)0.0356 (13)0.0026 (10)0.0014 (9)−0.0067 (10)
C50.0429 (12)0.0432 (12)0.0279 (12)0.0038 (10)0.0026 (9)−0.0006 (9)
C60.0386 (11)0.0378 (12)0.0288 (12)0.0050 (9)0.0026 (8)−0.0015 (8)
C70.0427 (11)0.0380 (11)0.0258 (11)0.0029 (10)0.0032 (8)−0.0015 (9)
C80.0392 (11)0.0380 (12)0.0364 (12)0.0033 (9)0.0063 (9)−0.0007 (9)
C90.0515 (13)0.0488 (14)0.0396 (14)−0.0017 (11)0.0056 (10)0.0038 (11)
C100.0593 (15)0.0536 (15)0.0581 (18)−0.0024 (12)0.0169 (13)0.0125 (12)
C110.0476 (13)0.0478 (14)0.075 (2)−0.0085 (11)0.0117 (13)0.0008 (13)
C120.0479 (14)0.0542 (15)0.0637 (18)−0.0065 (12)−0.0030 (12)−0.0065 (13)
C130.0534 (14)0.0517 (15)0.0412 (14)−0.0063 (12)0.0002 (11)0.0012 (11)
O1—C11.350 (3)C6—C71.498 (3)
O2—N11.229 (3)C8—C131.390 (3)
O3—N11.221 (3)C8—C91.386 (3)
O4—C71.243 (3)C9—C101.387 (4)
O1—H10.8200C10—C111.373 (4)
N1—C41.457 (3)C11—C121.376 (4)
N2—C81.420 (3)C12—C131.377 (3)
N2—C71.333 (3)C2—H20.9300
N2—H2A0.8600C3—H30.9300
C1—C61.408 (3)C5—H50.9300
C1—C21.393 (3)C9—H90.9300
C2—C31.367 (3)C10—H100.9300
C3—C41.389 (3)C11—H110.9300
C4—C51.369 (3)C12—H120.9300
C5—C61.391 (3)C13—H130.9300
O1···N22.675 (2)C8···C11viii3.480 (3)
O1···O4i2.609 (2)C8···C6vii3.583 (3)
O2···C11ii3.335 (4)C8···C1vii3.557 (3)
O3···C3iii3.364 (3)C9···C7vii3.339 (3)
O4···C2iv3.212 (3)C9···O42.853 (3)
O4···C92.853 (3)C9···C6vii3.556 (3)
O4···O1iv2.609 (2)C10···C7vii3.501 (3)
O4···C1iv3.319 (3)C11···C8vii3.480 (3)
O1···H2A1.9500C11···C3xi3.599 (4)
O2···H32.4500C11···O2xii3.335 (4)
O2···H12v2.7300C1···H2A2.5600
O2···H11ii2.5900C7···H92.8100
O3···H52.4000C7···H1iv2.7800
O3···H12vi2.7800H1···H22.2400
O3···H2iii2.8300H1···O4i1.7900
O3···H3iii2.7300H1···C7i2.7800
O4···H52.3900H1···H5i2.4800
O4···H92.2600H2···H12.2400
O4···H1iv1.7900H2···O3x2.8300
O4···H2iv2.5400H2···O4i2.5400
N2···O12.675 (2)H2A···O11.9500
N2···C1vii3.426 (3)H2A···C12.5600
C1···N2viii3.426 (3)H2A···H132.2600
C1···C8viii3.557 (3)H3···O22.4500
C1···O4i3.319 (3)H3···O3x2.7300
C2···O4i3.212 (3)H5···O32.4000
C3···C6viii3.478 (3)H5···O42.3900
C3···C11ix3.599 (4)H5···H1iv2.4800
C3···O3x3.364 (3)H9···O42.2600
C6···C8viii3.583 (3)H9···C72.8100
C6···C3vii3.478 (3)H11···O2xii2.5900
C6···C9viii3.556 (3)H12···O2xiii2.7300
C7···C10viii3.501 (3)H12···O3xiv2.7800
C7···C9viii3.339 (3)H13···H2A2.2600
C1—O1—H1109.00N2—C8—C13116.1 (2)
O2—N1—O3123.5 (2)C9—C8—C13119.5 (2)
O2—N1—C4117.9 (2)C8—C9—C10119.2 (2)
O3—N1—C4118.6 (2)C9—C10—C11121.2 (2)
C7—N2—C8128.92 (18)C10—C11—C12119.5 (2)
C8—N2—H2A116.00C11—C12—C13120.3 (2)
C7—N2—H2A116.00C8—C13—C12120.3 (2)
O1—C1—C2120.8 (2)C1—C2—H2119.00
O1—C1—C6119.16 (19)C3—C2—H2119.00
C2—C1—C6120.04 (19)C2—C3—H3121.00
C1—C2—C3121.5 (2)C4—C3—H3121.00
C2—C3—C4118.2 (2)C4—C5—H5120.00
N1—C4—C3119.6 (2)C6—C5—H5119.00
N1—C4—C5118.7 (2)C8—C9—H9120.00
C3—C4—C5121.7 (2)C10—C9—H9120.00
C4—C5—C6120.9 (2)C9—C10—H10119.00
C5—C6—C7116.10 (18)C11—C10—H10119.00
C1—C6—C7126.17 (19)C10—C11—H11120.00
C1—C6—C5117.73 (19)C12—C11—H11120.00
O4—C7—N2122.28 (19)C11—C12—H12120.00
O4—C7—C6119.55 (18)C13—C12—H12120.00
N2—C7—C6118.16 (18)C8—C13—H13120.00
N2—C8—C9124.4 (2)C12—C13—H13120.00
O3—N1—C4—C3−173.4 (2)N1—C4—C5—C6178.9 (2)
O2—N1—C4—C5−171.8 (2)C3—C4—C5—C6−0.4 (3)
O2—N1—C4—C37.4 (3)C4—C5—C6—C10.8 (3)
O3—N1—C4—C57.4 (3)C4—C5—C6—C7−178.9 (2)
C8—N2—C7—C6179.93 (17)C1—C6—C7—N24.2 (3)
C7—N2—C8—C9−6.5 (3)C5—C6—C7—O42.4 (3)
C8—N2—C7—O41.4 (3)C5—C6—C7—N2−176.16 (19)
C7—N2—C8—C13174.8 (2)C1—C6—C7—O4−177.2 (2)
C6—C1—C2—C30.8 (3)N2—C8—C9—C10−178.7 (2)
O1—C1—C6—C5179.3 (2)C13—C8—C9—C100.0 (4)
O1—C1—C2—C3−179.5 (2)N2—C8—C13—C12179.3 (2)
C2—C1—C6—C5−1.0 (3)C9—C8—C13—C120.5 (4)
C2—C1—C6—C7178.6 (2)C8—C9—C10—C110.1 (4)
O1—C1—C6—C7−1.2 (3)C9—C10—C11—C12−0.7 (4)
C1—C2—C3—C4−0.3 (3)C10—C11—C12—C131.1 (4)
C2—C3—C4—C50.1 (3)C11—C12—C13—C8−1.0 (4)
C2—C3—C4—N1−179.1 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.792.609 (2)176
N2—H2A···O10.861.952.675 (2)141
C2—H2···O4i0.932.543.212 (3)130
C5—H5···O40.932.392.729 (3)101
C9—H9···O40.932.262.853 (3)121
C11—H11···O2xii0.932.593.335 (4)137
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
O1—H1⋯O4i0.821.792.609 (2)176
N2—H2A⋯O10.861.952.675 (2)141
C2—H2⋯O4i0.932.543.212 (3)130
C9—H9⋯O40.932.262.853 (3)121
C11—H11⋯O2ii0.932.593.335 (4)137

Symmetry codes: (i) ; (ii) .

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