Literature DB >> 21588758

2-Hy-droxy-N-(3-nitro-phen-yl)benzamide.

Abdul Rauf Raza, Bushra Nisar, M Nawaz Tahir.   

Abstract

In the crystal structure of title compound, C(13)H(10)N(2)O(4), as expected, the nitro- and hy-droxy-substituted benzene rings are planar with r. m. s. deviations of 0.0037 and 0.0014 Å, respectively, but are twisted slightly relative to each other, making a dihedral angle of 12.23 (7)°. The nitro group is only slightly twisted [by 2.71 (16)°] with respect to its parent ring. An intra-molecular N-H⋯O hydrogen bond forms an S(6) ring motif. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds build up sheets parallel to the ab plane. Futhermore, weak π-π inter-actions [centroid-centroid distances = 3.7150 (8) 3.7342 (6) and 3.9421 (8) Å] between the rings yield a three-dimensional network.

Entities:  

Year:  2010        PMID： 21588758      PMCID： PMC3007834          DOI： 10.1107/S1600536810031910

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


Related literature

For the pharmaceutical properties of benzoxazepines and their derivatives, see: Fattorusso et al. (2005 ▶); Samanta et al. (2010 ▶). For related structures, see: Raza et al. (2009 ▶, 2010 ▶); Glidewell et al. (2006 ▶). For hydrogen-bonding discussion, see: Bernstein et al. (1995 ▶); Janiak (2000 ▶).

Experimental

Crystal data

C13H10N2O4 M = 258.23 Monoclinic, a = 7.8385 (2) Å b = 11.9531 (3) Å c = 12.3550 (3) Å β = 90.860 (1)° V = 1157.46 (5) Å3 Z = 4 Mo Kα radiation μ = 0.11 mm−1 T = 296 K 0.28 × 0.22 × 0.20 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 2874 independent reflections 2254 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.115 S = 1.03 2874 reflections 173 parameters H-atom parameters constrained Δρmax = 0.26 e Å−3 Δρmin = −0.19 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/S1600536810031910/dn2595sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031910/dn2595Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C13H10N2O4F(000) = 536
Mr = 258.23Dx = 1.482 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 931 reflections
a = 7.8385 (2) Åθ = 2.8–26.0°
b = 11.9531 (3) ŵ = 0.11 mm−1
c = 12.3550 (3) ÅT = 296 K
β = 90.860 (1)°Prisms, orange
V = 1157.46 (5) Å30.28 × 0.22 × 0.20 mm
Z = 4
Bruker Kappa APEXII CCD diffractometer2874 independent reflections
Radiation source: fine-focus sealed tube2254 reflections with I > 2σ(I)
graphiteRint = 0.023
Detector resolution: 7.5 pixels mm-1θmax = 28.3°, θmin = 2.4°
ω scansh = −10→8
Absorption correction: multi-scan (SADABS; Bruker, 2009)k = −15→15
Tmin = 0.979, Tmax = 0.988l = −16→15
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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0525P)2 + 0.2825P] where P = (Fo2 + 2Fc2)/3
2874 reflections(Δ/σ)max < 0.001
173 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.19 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.
xyzUiso*/Ueq
O10.67761 (15)0.72384 (9)0.11659 (11)0.0599 (4)
O20.87762 (16)0.63301 (11)0.04018 (13)0.0864 (6)
O30.19790 (13)0.61776 (7)0.25603 (10)0.0529 (3)
O4−0.01040 (12)0.30182 (7)0.25612 (9)0.0435 (3)
N10.25743 (14)0.43458 (8)0.23703 (10)0.0406 (4)
N20.74358 (15)0.63616 (11)0.08799 (10)0.0478 (4)
C10.41415 (16)0.43895 (10)0.18388 (11)0.0340 (4)
C20.50276 (16)0.53731 (10)0.16487 (11)0.0354 (4)
C30.65510 (16)0.53059 (11)0.11058 (11)0.0361 (4)
C40.72509 (18)0.43172 (12)0.07522 (12)0.0430 (4)
C50.63600 (18)0.33434 (12)0.09615 (12)0.0445 (4)
C60.48277 (18)0.33755 (11)0.14922 (11)0.0398 (4)
C70.15642 (15)0.51916 (9)0.26848 (11)0.0338 (4)
C8−0.00575 (15)0.48872 (10)0.32268 (10)0.0325 (3)
C9−0.08272 (16)0.38269 (10)0.31694 (10)0.0334 (3)
C10−0.23250 (17)0.36262 (11)0.37214 (12)0.0420 (4)
C11−0.30562 (19)0.44557 (12)0.43280 (13)0.0485 (5)
C12−0.23231 (19)0.55075 (12)0.43935 (12)0.0455 (4)
C13−0.08404 (17)0.57126 (11)0.38488 (11)0.0388 (4)
H10.220760.368540.251560.0487*
H20.460710.605860.188060.0424*
H40.828020.430430.038760.0516*
H4A−0.069980.245460.257310.0652*
H50.680080.265930.074130.0534*
H60.424270.271300.162120.0477*
H10−0.283730.292540.368040.0504*
H11−0.405530.430910.469890.0582*
H12−0.282770.606810.480100.0546*
H13−0.034490.641820.389510.0465*
U11U22U33U12U13U23
O10.0605 (7)0.0384 (6)0.0814 (8)−0.0136 (5)0.0186 (6)−0.0046 (5)
O20.0610 (8)0.0748 (9)0.1249 (13)−0.0213 (7)0.0524 (8)−0.0141 (8)
O30.0429 (5)0.0216 (4)0.0950 (8)0.0011 (4)0.0234 (5)0.0044 (5)
O40.0406 (5)0.0258 (4)0.0646 (6)−0.0064 (4)0.0155 (4)−0.0098 (4)
N10.0381 (6)0.0205 (5)0.0636 (8)−0.0002 (4)0.0166 (5)0.0025 (5)
N20.0407 (6)0.0484 (7)0.0546 (7)−0.0111 (5)0.0106 (5)−0.0035 (6)
C10.0324 (6)0.0275 (6)0.0421 (7)0.0017 (4)0.0040 (5)0.0012 (5)
C20.0326 (6)0.0278 (6)0.0459 (7)0.0016 (5)0.0043 (5)−0.0017 (5)
C30.0321 (6)0.0364 (7)0.0399 (7)−0.0026 (5)0.0014 (5)−0.0004 (5)
C40.0359 (7)0.0490 (8)0.0443 (7)0.0064 (6)0.0078 (5)−0.0028 (6)
C50.0491 (8)0.0358 (7)0.0489 (8)0.0123 (6)0.0063 (6)−0.0053 (6)
C60.0451 (7)0.0273 (6)0.0471 (7)0.0035 (5)0.0053 (6)−0.0010 (5)
C70.0321 (6)0.0239 (6)0.0456 (7)0.0005 (4)0.0046 (5)0.0016 (5)
C80.0329 (6)0.0250 (6)0.0398 (6)0.0002 (4)0.0035 (5)0.0019 (5)
C90.0340 (6)0.0259 (6)0.0405 (6)0.0007 (5)0.0038 (5)−0.0007 (5)
C100.0382 (7)0.0316 (6)0.0564 (8)−0.0060 (5)0.0102 (6)0.0003 (6)
C110.0417 (7)0.0442 (8)0.0603 (9)0.0001 (6)0.0209 (7)0.0005 (7)
C120.0483 (8)0.0367 (7)0.0520 (8)0.0073 (6)0.0154 (6)−0.0040 (6)
C130.0421 (7)0.0272 (6)0.0472 (7)0.0012 (5)0.0058 (6)−0.0015 (5)
O1—N21.2232 (17)C7—C81.4907 (17)
O2—N21.2136 (18)C8—C131.3981 (18)
O3—C71.2329 (14)C8—C91.4050 (17)
O4—C91.3540 (15)C9—C101.3875 (19)
O4—H4A0.8200C10—C111.373 (2)
N1—C11.4026 (17)C11—C121.384 (2)
N1—C71.3451 (15)C12—C131.374 (2)
N2—C31.4687 (18)C2—H20.9300
N1—H10.8600C4—H40.9300
C1—C61.3959 (18)C5—H50.9300
C1—C21.3874 (17)C6—H60.9300
C2—C31.3807 (18)C10—H100.9300
C3—C41.3768 (19)C11—H110.9300
C4—C51.384 (2)C12—H120.9300
C5—C61.378 (2)C13—H130.9300
O1···O4i3.1660 (16)C10···C5v3.564 (2)
O1···N1i3.1381 (16)C10···O3iv3.3407 (17)
O3···C10ii3.3407 (17)C12···C13x3.582 (2)
O3···C9ii3.4105 (15)C12···C8x3.4906 (19)
O3···O4ii2.6488 (13)C13···C13x3.5521 (19)
O3···C5i3.4148 (18)C13···O4ii3.3491 (16)
O3···C22.8257 (16)C13···C12x3.582 (2)
O4···N12.6450 (14)C7···H4Aii2.8100
O4···O1iii3.1660 (16)C7···H22.8000
O4···C13iv3.3491 (16)C9···H12.5300
O4···O3iv2.6488 (13)C10···H5xi3.0200
O4···C4v3.4009 (18)C11···H11xii2.9700
O4···C5v3.4022 (18)C11···H5xi3.0800
O1···H12vi2.6600C12···H11xii3.0800
O1···H22.3900C13···H4Aii2.9900
O1···H1i2.5000H1···O41.9800
O1···H6i2.9200H1···C92.5300
O2···H42.4500H1···H62.2700
O2···H4vii2.6300H1···O1iii2.5000
O3···H132.4900H2···O12.3900
O3···H10ii2.6800H2···O32.2400
O3···H22.2400H2···C72.8000
O3···H4Aii1.8300H4···O22.4500
O3···H5i2.9000H4···O2vii2.6300
O4···H11.9800H4A···H102.2500
O4···H13iv2.6500H4A···O3iv1.8300
N1···O42.6450 (14)H4A···C7iv2.8100
N1···O1iii3.1381 (16)H4A···C13iv2.9900
N2···C6viii3.4176 (18)H4A···H13iv2.3500
C2···O32.8257 (16)H5···O3iii2.9000
C2···C4viii3.459 (2)H5···C10xiii3.0200
C4···O4ix3.4009 (18)H5···C11xiii3.0800
C4···C9ix3.3759 (19)H6···H12.2700
C4···C2viii3.459 (2)H6···O1iii2.9200
C5···O4ix3.4022 (18)H10···H4A2.2500
C5···C9ix3.5293 (19)H10···O3iv2.6800
C5···C10ix3.564 (2)H11···C11xii2.9700
C5···O3iii3.4148 (18)H11···C12xii3.0800
C6···C10ix3.532 (2)H11···H11xii2.3500
C6···N2viii3.4176 (18)H11···H12xii2.5700
C8···C12x3.4906 (19)H12···H11xii2.5700
C9···C4v3.3759 (19)H12···O1xiv2.6600
C9···C5v3.5293 (19)H13···O32.4900
C9···O3iv3.4105 (15)H13···O4ii2.6500
C10···C6v3.532 (2)H13···H4Aii2.3500
C9—O4—H4A109.00C8—C9—C10119.81 (11)
C1—N1—C7129.11 (10)O4—C9—C8119.27 (11)
O1—N2—O2122.69 (13)O4—C9—C10120.92 (11)
O2—N2—C3118.72 (13)C9—C10—C11120.43 (12)
O1—N2—C3118.58 (12)C10—C11—C12120.75 (14)
C7—N1—H1115.00C11—C12—C13119.14 (13)
C1—N1—H1115.00C8—C13—C12121.66 (12)
N1—C1—C2123.71 (11)C1—C2—H2121.00
N1—C1—C6117.10 (11)C3—C2—H2121.00
C2—C1—C6119.19 (12)C3—C4—H4121.00
C1—C2—C3118.15 (11)C5—C4—H4121.00
N2—C3—C2117.17 (11)C4—C5—H5120.00
N2—C3—C4119.05 (12)C6—C5—H5120.00
C2—C3—C4123.76 (12)C1—C6—H6120.00
C3—C4—C5117.27 (13)C5—C6—H6120.00
C4—C5—C6120.77 (13)C9—C10—H10120.00
C1—C6—C5120.86 (12)C11—C10—H10120.00
N1—C7—C8117.13 (10)C10—C11—H11120.00
O3—C7—C8121.17 (11)C12—C11—H11120.00
O3—C7—N1121.67 (11)C11—C12—H12120.00
C7—C8—C9124.47 (11)C13—C12—H12120.00
C7—C8—C13117.32 (11)C8—C13—H13119.00
C9—C8—C13118.20 (11)C12—C13—H13119.00
C7—N1—C1—C27.6 (2)C4—C5—C6—C1−0.5 (2)
C7—N1—C1—C6−172.64 (13)O3—C7—C8—C9163.67 (13)
C1—N1—C7—O3−2.8 (2)O3—C7—C8—C13−17.53 (19)
C1—N1—C7—C8179.24 (12)N1—C7—C8—C9−18.36 (19)
O1—N2—C3—C2−1.05 (19)N1—C7—C8—C13160.43 (12)
O1—N2—C3—C4177.63 (13)C7—C8—C9—O4−2.03 (19)
O2—N2—C3—C2−179.85 (14)C7—C8—C9—C10178.87 (12)
O2—N2—C3—C4−1.2 (2)C13—C8—C9—O4179.19 (12)
N1—C1—C2—C3−179.31 (13)C13—C8—C9—C100.09 (18)
C6—C1—C2—C31.0 (2)C7—C8—C13—C12−178.94 (13)
N1—C1—C6—C5179.86 (13)C9—C8—C13—C12−0.1 (2)
C2—C1—C6—C5−0.4 (2)O4—C9—C10—C11−179.40 (13)
C1—C2—C3—N2177.89 (12)C8—C9—C10—C11−0.3 (2)
C1—C2—C3—C4−0.7 (2)C9—C10—C11—C120.5 (2)
N2—C3—C4—C5−178.69 (13)C10—C11—C12—C13−0.5 (2)
C2—C3—C4—C5−0.1 (2)C11—C12—C13—C80.3 (2)
C3—C4—C5—C60.7 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O40.861.982.6450 (14)133
N1—H1···O1iii0.862.503.1381 (16)132
O4—H4A···O3iv0.821.832.6488 (13)174
ring 1/ring 2ccd(Å)ipd(Å)sa(°)
Cg1->Cg2i3.7150 (8)3.45521.6
Cg3->Cg4ii3.7342 (6)3.53918.6
Cg5->Cg5iii3.9421 (8)3.44329.1
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O40.861.982.6450 (14)133
N1—H1⋯O1i0.862.503.1381 (16)132
O4—H4A⋯O3ii0.821.832.6488 (13)174

Symmetry codes: (i) ; (ii) .

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  3 in total

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  3 in total

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