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In the title compound, C13H12N2O2·H2O, all bond lengths and angles are normal. The hydr­oxy group is involved in hydrogen bonding, which links the mol­ecules into centrosymmetric dimers. The solvent water mol­ecules, acting as donors and acceptors of hydrogen bonds, link the dimers into two-dimensional sheets. The crystal packing is further stabilized by weak inter­molecular C—H...O inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806031205/cv2093sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806031205/cv2093Isup2.hkl
Contains datablock I

CCDC reference: 620780

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.051
  • wR factor = 0.162
  • Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

2-Hydroxy-N-(2-pyridylmethyl)benzamide monohydrate top
Crystal data top
C13H12N2O2·H2OF(000) = 520
Mr = 246.26Dx = 1.328 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.849 (3) ÅCell parameters from 704 reflections
b = 4.6324 (13) Åθ = 2.8–21.2°
c = 25.094 (6) ŵ = 0.10 mm1
β = 102.484 (9)°T = 293 K
V = 1231.3 (6) Å3Needle, colourless
Z = 40.50 × 0.14 × 0.07 mm
Data collection top
Siemens SMART 1000 CCD area-detector
diffractometer
2434 independent reflections
Radiation source: fine-focus sealed tube1321 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
Detector resolution: 8.33 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 1311
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 55
Tmin = 0.954, Tmax = 0.993l = 3026
6488 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162H atoms treated by a mixture of independent and constrained refinement
S = 0.89 w = 1/[σ2(Fo2) + (0.0862P)2 + 0.05P]
where P = (Fo2 + 2Fc2)/3
2434 reflections(Δ/σ)max < 0.001
171 parametersΔρmax = 0.15 e Å3
2 restraintsΔρmin = 0.13 e Å3
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
N10.08696 (18)1.1798 (5)0.09097 (8)0.0467 (6)
H1A0.07311.15990.05610.056*
O10.15356 (17)0.9487 (4)0.00438 (7)0.0629 (6)
H1B0.15730.90940.02710.094*
O20.19698 (17)1.0424 (4)0.17269 (7)0.0584 (6)
N20.1750 (2)1.0794 (5)0.09991 (9)0.0511 (6)
C10.2431 (2)0.7951 (6)0.03973 (10)0.0465 (7)
C60.2554 (2)0.8271 (5)0.09591 (10)0.0409 (6)
C50.3467 (2)0.6628 (6)0.13035 (11)0.0500 (7)
H5A0.35490.67980.16790.060*
C20.3217 (3)0.6055 (7)0.02009 (12)0.0587 (8)
H2B0.31350.58400.01740.070*
C70.1783 (2)1.0254 (5)0.12258 (10)0.0427 (6)
C80.0109 (2)1.3799 (6)0.11431 (12)0.0527 (7)
H8A0.02591.52020.08680.063*
H8B0.06511.48320.14400.063*
C90.0930 (2)1.2358 (5)0.13541 (10)0.0449 (7)
C100.1043 (3)1.2657 (7)0.18849 (12)0.0660 (9)
H10A0.04601.37510.21290.079*
C30.4114 (3)0.4495 (6)0.05536 (13)0.0612 (8)
H3A0.46360.32380.04160.073*
C110.2032 (3)1.1316 (9)0.20538 (13)0.0775 (10)
H11A0.21261.15150.24120.093*
C130.2695 (3)0.9513 (7)0.11734 (13)0.0652 (8)
H13A0.32690.84240.09240.078*
C40.4250 (3)0.4769 (6)0.11091 (13)0.0590 (8)
H4A0.48600.37140.13480.071*
C120.2866 (3)0.9706 (7)0.16912 (14)0.0699 (9)
H12A0.35340.87650.17950.084*
O1W0.4320 (2)0.1529 (5)0.24401 (10)0.0716 (6)
H2W0.3624 (18)0.128 (8)0.2214 (11)0.094 (13)*
H1W0.475 (3)0.003 (5)0.2490 (16)0.103 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0432 (12)0.0560 (14)0.0403 (12)0.0004 (11)0.0079 (10)0.0035 (11)
O10.0527 (12)0.0989 (15)0.0360 (10)0.0150 (11)0.0071 (9)0.0024 (11)
O20.0552 (12)0.0806 (14)0.0379 (11)0.0057 (10)0.0069 (9)0.0050 (10)
N20.0507 (14)0.0627 (14)0.0417 (13)0.0044 (12)0.0140 (11)0.0037 (12)
C10.0367 (14)0.0583 (17)0.0433 (16)0.0049 (13)0.0061 (12)0.0004 (14)
C60.0350 (13)0.0451 (15)0.0419 (15)0.0090 (11)0.0062 (11)0.0020 (12)
C50.0514 (16)0.0557 (16)0.0418 (15)0.0024 (14)0.0073 (13)0.0023 (14)
C20.0501 (17)0.080 (2)0.0498 (17)0.0008 (16)0.0187 (14)0.0065 (16)
C70.0368 (14)0.0499 (16)0.0407 (15)0.0102 (12)0.0068 (12)0.0005 (13)
C80.0510 (17)0.0499 (16)0.0578 (18)0.0026 (13)0.0131 (14)0.0018 (14)
C90.0433 (15)0.0489 (16)0.0415 (16)0.0084 (12)0.0068 (12)0.0009 (13)
C100.0608 (19)0.087 (2)0.0483 (18)0.0047 (17)0.0082 (15)0.0100 (17)
C30.0530 (18)0.0623 (19)0.074 (2)0.0022 (15)0.0267 (16)0.0086 (17)
C110.074 (2)0.117 (3)0.0492 (18)0.018 (2)0.0299 (18)0.006 (2)
C130.0527 (18)0.076 (2)0.068 (2)0.0099 (16)0.0157 (16)0.0030 (17)
C40.0526 (18)0.0579 (18)0.066 (2)0.0064 (14)0.0127 (15)0.0055 (16)
C120.058 (2)0.088 (2)0.070 (2)0.0066 (17)0.0286 (17)0.015 (2)
O1W0.0620 (15)0.0675 (16)0.0752 (16)0.0019 (13)0.0075 (12)0.0134 (13)
Geometric parameters (Å, º) top
N1—C71.336 (3)C8—C91.501 (3)
N1—C81.446 (3)C8—H8A0.9700
N1—H1A0.8600C8—H8B0.9700
O1—C11.365 (3)C9—C101.371 (4)
O1—H1B0.8200C10—C111.384 (4)
O2—C71.232 (3)C10—H10A0.9300
N2—C91.330 (3)C3—C41.375 (4)
N2—C131.337 (3)C3—H3A0.9300
C1—C21.387 (4)C11—C121.359 (4)
C1—C61.395 (3)C11—H11A0.9300
C6—C51.392 (3)C13—C121.355 (4)
C6—C71.494 (4)C13—H13A0.9300
C5—C41.371 (4)C4—H4A0.9300
C5—H5A0.9300C12—H12A0.9300
C2—C31.371 (4)O1W—H2W0.85 (2)
C2—H2B0.9300O1W—H1W0.85 (3)
C7—N1—C8121.2 (2)C9—C8—H8B108.9
C7—N1—H1A119.4H8A—C8—H8B107.7
C8—N1—H1A119.4N2—C9—C10121.2 (2)
C1—O1—H1B109.5N2—C9—C8116.8 (2)
C9—N2—C13118.2 (2)C10—C9—C8122.0 (3)
O1—C1—C2120.3 (2)C9—C10—C11119.4 (3)
O1—C1—C6120.0 (2)C9—C10—H10A120.3
C2—C1—C6119.6 (3)C11—C10—H10A120.3
C5—C6—C1118.0 (2)C2—C3—C4120.7 (3)
C5—C6—C7116.7 (2)C2—C3—H3A119.6
C1—C6—C7125.3 (2)C4—C3—H3A119.6
C4—C5—C6122.3 (3)C12—C11—C10119.3 (3)
C4—C5—H5A118.8C12—C11—H11A120.3
C6—C5—H5A118.8C10—C11—H11A120.3
C3—C2—C1120.6 (3)N2—C13—C12123.9 (3)
C3—C2—H2B119.7N2—C13—H13A118.0
C1—C2—H2B119.7C12—C13—H13A118.0
O2—C7—N1120.6 (2)C5—C4—C3118.7 (3)
O2—C7—C6120.8 (2)C5—C4—H4A120.7
N1—C7—C6118.6 (2)C3—C4—H4A120.7
N1—C8—C9113.3 (2)C13—C12—C11118.0 (3)
N1—C8—H8A108.9C13—C12—H12A121.0
C9—C8—H8A108.9C11—C12—H12A121.0
N1—C8—H8B108.9H2W—O1W—H1W111 (4)
O1—C1—C6—C5179.0 (2)C7—N1—C8—C980.1 (3)
C2—C1—C6—C50.5 (4)C13—N2—C9—C100.1 (4)
O1—C1—C6—C71.2 (4)C13—N2—C9—C8179.2 (2)
C2—C1—C6—C7179.3 (2)N1—C8—C9—N257.4 (3)
C1—C6—C5—C41.0 (4)N1—C8—C9—C10123.3 (3)
C7—C6—C5—C4178.8 (2)N2—C9—C10—C110.3 (4)
O1—C1—C2—C3179.7 (2)C8—C9—C10—C11178.9 (3)
C6—C1—C2—C30.1 (4)C1—C2—C3—C40.3 (4)
C8—N1—C7—O22.7 (4)C9—C10—C11—C120.6 (5)
C8—N1—C7—C6178.7 (2)C9—N2—C13—C120.2 (4)
C5—C6—C7—O20.8 (3)C6—C5—C4—C30.8 (4)
C1—C6—C7—O2179.0 (2)C2—C3—C4—C50.2 (4)
C5—C6—C7—N1177.8 (2)N2—C13—C12—C110.5 (5)
C1—C6—C7—N12.3 (4)C10—C11—C12—C130.7 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O10.861.972.659 (3)136
C5—H5A···O20.932.422.758 (3)101
O1—H1B···N2i0.821.882.680 (3)165
O1W—H1W···O1Wii0.85 (3)1.87 (3)2.728 (3)177 (4)
O1W—H2W···O2iii0.85 (2)1.98 (2)2.827 (3)175 (3)
C12—H12A···O1Wiv0.932.493.300 (4)146
Symmetry codes: (i) x, y+2, z; (ii) x+1, y1/2, z+1/2; (iii) x, y1, z; (iv) x, y+1/2, z+1/2.
 

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