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The mol­ecule of the title compound, C12H10N2O2, is nearly planar, with a dihedral angle of 3.7 (2)° between the planes of the benzene and pyridine rings. Mol­ecules are linked by inter­molecular O—H...N and C—H...O hydrogen bonds, as well as possible C—H...π inter­actions, forming a two-dimensional zigzag hydrogen-bonded network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012244/hk2022sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012244/hk2022Isup2.hkl
Contains datablock I

CCDC reference: 277691

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.046
  • wR factor = 0.135
  • Data-to-parameter ratio = 7.4

checkCIF/PLATON results

No syntax errors found



Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.106 STRVA01_ALERT_2_C Chirality of atom sites is inverted? From the CIF: _refine_ls_abs_structure_Flack 10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.11 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 10.00 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.41 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.03 From the CIF: _reflns_number_total 1074 Count of symmetry unique reflns 1074 Completeness (_total/calc) 100.00% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2005); software used to prepare material for publication: SHELXTL (Bruker, 2000).

2-Hydroxy-N-(2-pyridyl)benzamide top
Crystal data top
C12H10N2O2F(000) = 448
Mr = 214.22Dx = 1.392 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 903 reflections
a = 6.1216 (16) Åθ = 2.2–20.5°
b = 12.535 (3) ŵ = 0.10 mm1
c = 13.321 (4) ÅT = 298 K
V = 1022.2 (5) Å3Needle, colorless
Z = 40.48 × 0.19 × 0.17 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1074 independent reflections
Radiation source: fine-focus sealed tube671 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.106
φ and ω scansθmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 77
Tmin = 0.955, Tmax = 0.984k = 1414
5265 measured reflectionsl = 1510
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.135 w = 1/[σ2(Fo2) + (0.062P)2 + 0.1271P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
1074 reflectionsΔρmax = 0.18 e Å3
145 parametersΔρmin = 0.17 e Å3
0 restraintsAbsolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 10 (10)
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N11.0593 (6)0.0508 (3)0.4239 (3)0.0423 (10)
H11.04060.11430.44690.051*
N21.3572 (6)0.0537 (3)0.5262 (3)0.0427 (9)
O10.9183 (6)0.0704 (2)0.3171 (3)0.0644 (10)
O20.8700 (6)0.2389 (2)0.4265 (3)0.0637 (11)
H20.84060.30090.44090.096*
C10.9106 (8)0.0175 (3)0.3557 (3)0.0420 (11)
C20.7368 (7)0.0945 (3)0.3287 (3)0.0399 (10)
C30.7180 (7)0.2007 (3)0.3616 (3)0.0421 (12)
C40.5473 (8)0.2626 (4)0.3291 (4)0.0561 (13)
H40.53810.33310.35070.067*
C50.3906 (9)0.2239 (4)0.2660 (4)0.0587 (14)
H50.27600.26730.24520.070*
C60.4039 (8)0.1197 (4)0.2334 (4)0.0564 (14)
H60.29880.09200.19030.068*
C70.5746 (7)0.0575 (4)0.2656 (3)0.0474 (12)
H70.58140.01290.24380.057*
C81.2375 (7)0.0039 (3)0.4615 (3)0.0383 (11)
C91.2951 (8)0.1068 (3)0.4358 (4)0.0497 (13)
H91.21260.14570.39010.060*
C101.4762 (9)0.1499 (4)0.4795 (4)0.0581 (14)
H101.51710.21930.46360.070*
C111.5982 (9)0.0928 (4)0.5460 (4)0.0593 (14)
H111.72220.12190.57560.071*
C121.5330 (8)0.0076 (4)0.5676 (4)0.0508 (13)
H121.61430.04670.61370.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.046 (2)0.0293 (18)0.051 (2)0.0047 (18)0.004 (2)0.0074 (18)
N20.049 (2)0.0356 (19)0.044 (2)0.0020 (19)0.001 (2)0.0025 (18)
O10.073 (2)0.0400 (18)0.080 (2)0.0080 (19)0.017 (2)0.0244 (18)
O20.078 (2)0.0333 (17)0.080 (2)0.0109 (18)0.030 (2)0.0160 (18)
C10.048 (3)0.032 (2)0.047 (3)0.006 (2)0.003 (2)0.004 (2)
C20.042 (2)0.037 (2)0.040 (2)0.004 (2)0.000 (2)0.002 (2)
C30.050 (3)0.032 (2)0.044 (3)0.002 (2)0.001 (2)0.001 (2)
C40.072 (3)0.035 (3)0.061 (3)0.007 (3)0.012 (3)0.004 (3)
C50.059 (3)0.060 (3)0.058 (3)0.008 (3)0.007 (3)0.013 (3)
C60.053 (3)0.063 (3)0.053 (3)0.001 (3)0.008 (3)0.003 (3)
C70.053 (3)0.047 (3)0.042 (3)0.005 (3)0.000 (3)0.006 (2)
C80.043 (2)0.032 (2)0.040 (2)0.004 (2)0.007 (2)0.001 (2)
C90.060 (3)0.033 (3)0.057 (3)0.004 (2)0.006 (3)0.009 (2)
C100.070 (3)0.038 (3)0.066 (3)0.007 (3)0.001 (3)0.007 (3)
C110.066 (3)0.052 (3)0.060 (3)0.010 (3)0.000 (3)0.008 (3)
C120.052 (3)0.051 (3)0.049 (3)0.000 (3)0.003 (3)0.005 (2)
Geometric parameters (Å, º) top
N1—C11.353 (5)C5—C61.378 (6)
N1—C81.382 (5)C5—H50.9300
N1—H10.8600C6—C71.372 (6)
N2—C121.340 (6)C6—H60.9300
N2—C81.342 (5)C7—H70.9300
O1—C11.217 (5)C8—C91.381 (6)
O2—C31.358 (5)C9—C101.363 (6)
O2—H20.8200C9—H90.9300
C1—C21.481 (6)C10—C111.362 (6)
C2—C71.381 (6)C10—H100.9300
C2—C31.406 (5)C11—C121.351 (6)
C3—C41.372 (6)C11—H110.9300
C4—C51.366 (6)C12—H120.9300
C4—H40.9300
C1—N1—C8128.4 (4)C7—C6—H6120.5
C1—N1—H1115.8C5—C6—H6120.5
C8—N1—H1115.8C6—C7—C2123.1 (4)
C12—N2—C8118.1 (4)C6—C7—H7118.4
C3—O2—H2109.5C2—C7—H7118.4
O1—C1—N1122.5 (5)N2—C8—C9121.5 (4)
O1—C1—C2121.0 (4)N2—C8—N1113.4 (4)
N1—C1—C2116.4 (4)C9—C8—N1125.2 (4)
C7—C2—C3116.7 (4)C10—C9—C8118.2 (5)
C7—C2—C1116.5 (4)C10—C9—H9120.9
C3—C2—C1126.9 (4)C8—C9—H9120.9
O2—C3—C4121.5 (4)C11—C10—C9121.0 (5)
O2—C3—C2118.5 (4)C11—C10—H10119.5
C4—C3—C2120.0 (4)C9—C10—H10119.5
C5—C4—C3121.9 (5)C12—C11—C10117.8 (5)
C5—C4—H4119.1C12—C11—H11121.1
C3—C4—H4119.1C10—C11—H11121.1
C4—C5—C6119.3 (5)N2—C12—C11123.5 (5)
C4—C5—H5120.4N2—C12—H12118.3
C6—C5—H5120.4C11—C12—H12118.3
C7—C6—C5119.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.861.902.627 (5)142
O2—H2···N2i0.821.882.676 (5)164
C5—H5···O1ii0.932.503.384 (6)159
Symmetry codes: (i) x1/2, y+1/2, z+1; (ii) x+1, y+1/2, z+1/2.
 

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