2-Hydr­oxy-N-(2-pyrid­yl)benzamide

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.

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

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Computing details

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

Crystal data

C12H10N2O2	F(000) = 448
Mr = 214.22	Dx = 1.392 Mg m^−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 903 reflections
a = 6.1216 (16) Å	θ = 2.2–20.5°
b = 12.535 (3) Å	µ = 0.10 mm^−1
c = 13.321 (4) Å	T = 298 K
V = 1022.2 (5) Å^3	Needle, colorless
Z = 4	0.48 × 0.19 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1074 independent reflections
Radiation source: fine-focus sealed tube	671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.106
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.955, Tmax = 0.984	k = −14→14
5265 measured reflections	l = −15→10

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.135	w = 1/[σ^2(Fo^2) + (0.062P)^2 + 0.1271P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
1074 reflections	Δρmax = 0.18 e Å^−3
145 parameters	Δρmin = −0.17 e Å^−3
0 restraints	Absolute structure: Flack (1983), no Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 10 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	1.0593 (6)	0.0508 (3)	0.4239 (3)	0.0423 (10)
H1	1.0406	0.1143	0.4469	0.051*
N2	1.3572 (6)	0.0537 (3)	0.5262 (3)	0.0427 (9)
O1	0.9183 (6)	−0.0704 (2)	0.3171 (3)	0.0644 (10)
O2	0.8700 (6)	0.2389 (2)	0.4265 (3)	0.0637 (11)
H2	0.8406	0.3009	0.4409	0.096*
C1	0.9106 (8)	0.0175 (3)	0.3557 (3)	0.0420 (11)
C2	0.7368 (7)	0.0945 (3)	0.3287 (3)	0.0399 (10)
C3	0.7180 (7)	0.2007 (3)	0.3616 (3)	0.0421 (12)
C4	0.5473 (8)	0.2626 (4)	0.3291 (4)	0.0561 (13)
H4	0.5381	0.3331	0.3507	0.067*
C5	0.3906 (9)	0.2239 (4)	0.2660 (4)	0.0587 (14)
H5	0.2760	0.2673	0.2452	0.070*
C6	0.4039 (8)	0.1197 (4)	0.2334 (4)	0.0564 (14)
H6	0.2988	0.0920	0.1903	0.068*
C7	0.5746 (7)	0.0575 (4)	0.2656 (3)	0.0474 (12)
H7	0.5814	−0.0129	0.2438	0.057*
C8	1.2375 (7)	−0.0039 (3)	0.4615 (3)	0.0383 (11)
C9	1.2951 (8)	−0.1068 (3)	0.4358 (4)	0.0497 (13)
H9	1.2126	−0.1457	0.3901	0.060*
C10	1.4762 (9)	−0.1499 (4)	0.4795 (4)	0.0581 (14)
H10	1.5171	−0.2193	0.4636	0.070*
C11	1.5982 (9)	−0.0928 (4)	0.5460 (4)	0.0593 (14)
H11	1.7222	−0.1219	0.5756	0.071*
C12	1.5330 (8)	0.0076 (4)	0.5676 (4)	0.0508 (13)
H12	1.6143	0.0467	0.6137	0.061*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.046 (2)	0.0293 (18)	0.051 (2)	0.0047 (18)	−0.004 (2)	−0.0074 (18)
N2	0.049 (2)	0.0356 (19)	0.044 (2)	−0.0020 (19)	0.001 (2)	−0.0025 (18)
O1	0.073 (2)	0.0400 (18)	0.080 (2)	0.0080 (19)	−0.017 (2)	−0.0244 (18)
O2	0.078 (2)	0.0333 (17)	0.080 (2)	0.0109 (18)	−0.030 (2)	−0.0160 (18)
C1	0.048 (3)	0.032 (2)	0.047 (3)	−0.006 (2)	0.003 (2)	−0.004 (2)
C2	0.042 (2)	0.037 (2)	0.040 (2)	−0.004 (2)	0.000 (2)	0.002 (2)
C3	0.050 (3)	0.032 (2)	0.044 (3)	−0.002 (2)	−0.001 (2)	−0.001 (2)
C4	0.072 (3)	0.035 (3)	0.061 (3)	0.007 (3)	−0.012 (3)	0.004 (3)
C5	0.059 (3)	0.060 (3)	0.058 (3)	0.008 (3)	−0.007 (3)	0.013 (3)
C6	0.053 (3)	0.063 (3)	0.053 (3)	−0.001 (3)	−0.008 (3)	−0.003 (3)
C7	0.053 (3)	0.047 (3)	0.042 (3)	−0.005 (3)	0.000 (3)	−0.006 (2)
C8	0.043 (2)	0.032 (2)	0.040 (2)	−0.004 (2)	0.007 (2)	0.001 (2)
C9	0.060 (3)	0.033 (3)	0.057 (3)	0.004 (2)	−0.006 (3)	−0.009 (2)
C10	0.070 (3)	0.038 (3)	0.066 (3)	0.007 (3)	−0.001 (3)	−0.007 (3)
C11	0.066 (3)	0.052 (3)	0.060 (3)	0.010 (3)	0.000 (3)	−0.008 (3)
C12	0.052 (3)	0.051 (3)	0.049 (3)	0.000 (3)	−0.003 (3)	−0.005 (2)

Geometric parameters (Å, º)

N1—C1	1.353 (5)	C5—C6	1.378 (6)
N1—C8	1.382 (5)	C5—H5	0.9300
N1—H1	0.8600	C6—C7	1.372 (6)
N2—C12	1.340 (6)	C6—H6	0.9300
N2—C8	1.342 (5)	C7—H7	0.9300
O1—C1	1.217 (5)	C8—C9	1.381 (6)
O2—C3	1.358 (5)	C9—C10	1.363 (6)
O2—H2	0.8200	C9—H9	0.9300
C1—C2	1.481 (6)	C10—C11	1.362 (6)
C2—C7	1.381 (6)	C10—H10	0.9300
C2—C3	1.406 (5)	C11—C12	1.351 (6)
C3—C4	1.372 (6)	C11—H11	0.9300
C4—C5	1.366 (6)	C12—H12	0.9300
C4—H4	0.9300
C1—N1—C8	128.4 (4)	C7—C6—H6	120.5
C1—N1—H1	115.8	C5—C6—H6	120.5
C8—N1—H1	115.8	C6—C7—C2	123.1 (4)
C12—N2—C8	118.1 (4)	C6—C7—H7	118.4
C3—O2—H2	109.5	C2—C7—H7	118.4
O1—C1—N1	122.5 (5)	N2—C8—C9	121.5 (4)
O1—C1—C2	121.0 (4)	N2—C8—N1	113.4 (4)
N1—C1—C2	116.4 (4)	C9—C8—N1	125.2 (4)
C7—C2—C3	116.7 (4)	C10—C9—C8	118.2 (5)
C7—C2—C1	116.5 (4)	C10—C9—H9	120.9
C3—C2—C1	126.9 (4)	C8—C9—H9	120.9
O2—C3—C4	121.5 (4)	C11—C10—C9	121.0 (5)
O2—C3—C2	118.5 (4)	C11—C10—H10	119.5
C4—C3—C2	120.0 (4)	C9—C10—H10	119.5
C5—C4—C3	121.9 (5)	C12—C11—C10	117.8 (5)
C5—C4—H4	119.1	C12—C11—H11	121.1
C3—C4—H4	119.1	C10—C11—H11	121.1
C4—C5—C6	119.3 (5)	N2—C12—C11	123.5 (5)
C4—C5—H5	120.4	N2—C12—H12	118.3
C6—C5—H5	120.4	C11—C12—H12	118.3
C7—C6—C5	119.0 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	1.90	2.627 (5)	142
O2—H2···N2^i	0.82	1.88	2.676 (5)	164
C5—H5···O1^ii	0.93	2.50	3.384 (6)	159

Symmetry codes: (i) x−1/2, −y+1/2, −z+1; (ii) −x+1, y+1/2, −z+1/2.