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Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o659.
Published online 2009 March 6. doi:  10.1107/S1600536809006916
PMCID: PMC2968923

N′-(Diphenyl­methyl­ene)-2-hydroxy­benzo­hydrazide

Abstract

In the title compound, C20H16N2O2, intra­molecular N—H(...)O and inter­molecular O—H(...)O hydrogen bonds are found. The inter­molecular hydrogen bonds link the mol­ecules into an infinite chain along the c axis. The dihedral angles between the aromatic rings are 16.9 (3), 80.8 (3) and 64.6 (3)°

Related literature

For the multiple-coordination environment of 2-hydroxybenzohydrazide and its derivatives, see: Chang (2008 [triangle]); Huo et al. (2004 [triangle]).

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Object name is e-65-0o659-scheme1.jpg

Experimental

Crystal data

  • C20H16N2O2
  • M r = 316.35
  • Tetragonal, An external file that holds a picture, illustration, etc.
Object name is e-65-0o659-efi3.jpg
  • a = 16.5157 (9) Å
  • c = 24.401 (3) Å
  • V = 6655.8 (10) Å3
  • Z = 16
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 273 K
  • 0.31 × 0.25 × 0.19 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.972, T max = 0.987
  • 17393 measured reflections
  • 2929 independent reflections
  • 1610 reflections with I > 2σ(I)
  • R int = 0.096

Refinement

  • R[F 2 > 2σ(F 2)] = 0.072
  • wR(F 2) = 0.255
  • S = 1.01
  • 2929 reflections
  • 217 parameters
  • 7 restraints
  • H-atom parameters constrained
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.47 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006916/rk2128sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006916/rk2128Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the Postgraduate Foundation of Taishan University (No. Y07–2–15) for financial support.

supplementary crystallographic information

Comment

The chemistry of 2-hydroxybenzohydrazide and its derivatives are studied because of their multiply coordination environment (Chang, 2008; Huo et al., 2004). They represent a class of highly useful compounds in which the presence of O and N atom renders various hydrogen bonding motifs leading to the formation of versatile architecture in the crystal lattice. As the continue of the aspect, we study the reaction of benzophenone and 2–hydroxybenzohydrazide in the state of refluxing in ethanol.

Herein we report the molecular (Fig. 1) and crystal structures of the title compound, C20H16N2O2, which was characterized by elemental analyses too. In the structure an intramolecular N2—H2B···O2 (Fig. 1) and an intermolecular O2—H2A···O1i (Fig. 2) H–bonds were found. Symmetry code: (i) 3/4-y, 1/4+x, 1/4+z).

Experimental

Benzophenone and 2–hydroxybenzohydrazide were added to the solvent of ethanol and the mixture was stirred for 4 h at 323 K. After cooling down to the room temperature, the solution was filtered. The solvent was removed from the filtrate under vacuum and the solid residue was recrystallized from ether; colourless crystals suitable for X–ray diffraction study were obtained. Yield, 79%. m.p. 463 K. Analysis, calculated for C20H16N2O2: C 79.19, H 5.65, N 4.62; found: C 79.36, H 5.43, N 4.35%. The elemental analyses were performed with a Perkine Elemer PE2400II instrument.

Refinement

The all H atoms were placed in idealized positions and constrained to ride on their parent atoms, with distances: N—H = 0.86 Å and O—H = 0.82 Å, C—H = 0.93 Å. The Uiso(H) values were set at 1.2Ueq(parent C, N) and 1.5Ueq(O).

Figures

Fig. 1.
The molecular structure of the title compound with the atom numbering scheme. The displacement ellipsoids are shown at 30% probability level. H atoms are presented as a small spheres of arbitrary radius. Intramolecular H–bond shown by dashed line. ...
Fig. 2.
The one–dimensional chains are formed by the intermolecular H–bonds O2—H2···O1i. Symmetry code: (i) 3/4-y, 1/4+x, 1/4+z.

Crystal data

C20H16N2O2Dx = 1.263 Mg m3
Mr = 316.35Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I41/aCell parameters from 3007 reflections
Hall symbol: -I 4adθ = 2.4–20.0°
a = 16.5157 (9) ŵ = 0.08 mm1
c = 24.401 (3) ÅT = 273 K
V = 6655.8 (10) Å3Block, colourless
Z = 160.31 × 0.25 × 0.19 mm
F(000) = 2672

Data collection

Bruker SMART CCD area-detector diffractometer2929 independent reflections
Radiation source: Fine–focus sealed tube1610 reflections with I > 2σ(I)
GraphiteRint = 0.096
[var phi] and ω scansθmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −19→17
Tmin = 0.972, Tmax = 0.987k = −19→19
17393 measured reflectionsl = −24→28

Refinement

Refinement on F2Primary atom site location: Direct
Least-squares matrix: FullSecondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: Geom
wR(F2) = 0.255H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.158P)2 + 0.5238P] where P = (Fo2 + 2Fc2)/3
2929 reflections(Δ/σ)max = 0.001
217 parametersΔρmax = 0.53 e Å3
7 restraintsΔρmin = −0.47 e Å3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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)

xyzUiso*/Ueq
N10.19770 (16)0.48883 (16)0.91131 (10)0.0673 (8)
N20.20636 (16)0.53442 (16)0.95782 (10)0.0660 (8)
H2B0.18280.51970.98760.079*
O10.28234 (15)0.62777 (14)0.91455 (9)0.0834 (8)
O20.18133 (14)0.55740 (15)1.06333 (8)0.0770 (7)
H2A0.16810.54931.09530.115*
C10.1847 (2)0.3933 (2)0.81748 (16)0.0892 (12)
H10.21220.44220.81480.107*
C20.1798 (3)0.3438 (3)0.77280 (18)0.1029 (13)
H20.20360.35960.73990.123*
C30.1404 (3)0.2713 (3)0.7760 (2)0.1021 (14)
H30.13820.23730.74560.123*
C40.1046 (3)0.2494 (3)0.8232 (2)0.1024 (14)
H40.07650.20070.82510.123*
C50.1094 (2)0.2984 (2)0.86910 (18)0.0894 (12)
H50.08550.28190.90180.107*
C60.1494 (2)0.3717 (2)0.86662 (14)0.0696 (9)
C70.15649 (19)0.4228 (2)0.91578 (13)0.0655 (9)
C80.1194 (2)0.3957 (2)0.96790 (14)0.0708 (9)
C90.0389 (3)0.4050 (3)0.9779 (2)0.1276 (19)
H90.00550.42800.95150.153*
C100.0067 (4)0.3801 (3)1.0278 (3)0.1355 (17)
H10−0.04880.38351.03410.163*
C110.0576 (4)0.3502 (4)1.0679 (2)0.150 (2)
H110.03680.33851.10240.180*
C120.1362 (4)0.3380 (3)1.0581 (2)0.1236 (18)
H120.16930.31451.08450.148*
C130.1676 (3)0.3610 (3)1.00770 (17)0.0944 (13)
H130.22230.35281.00060.113*
C140.2516 (2)0.6023 (2)0.95709 (12)0.0625 (8)
C150.26762 (18)0.64251 (19)1.01038 (12)0.0585 (8)
C160.2366 (2)0.6184 (2)1.06129 (12)0.0648 (9)
C170.2630 (3)0.6562 (3)1.10856 (14)0.0864 (11)
H170.24360.63891.14230.104*
C180.3167 (3)0.7181 (3)1.10648 (16)0.0967 (13)
H180.33340.74301.13880.116*
C190.3466 (2)0.7445 (3)1.05717 (16)0.0904 (12)
H190.38300.78741.05570.108*
C200.3218 (2)0.7066 (2)1.01018 (14)0.0752 (10)
H200.34220.72460.97680.090*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
N10.0836 (19)0.0705 (17)0.0477 (15)−0.0095 (15)0.0066 (13)−0.0014 (12)
N20.0788 (18)0.0773 (18)0.0418 (14)−0.0052 (14)0.0106 (12)0.0011 (12)
O10.1105 (19)0.0922 (17)0.0476 (13)−0.0258 (14)0.0190 (12)−0.0067 (12)
O20.0928 (17)0.0963 (17)0.0417 (12)−0.0020 (14)0.0095 (11)0.0066 (11)
C10.107 (3)0.090 (3)0.070 (3)−0.021 (2)0.003 (2)−0.007 (2)
C20.128 (4)0.108 (3)0.073 (3)−0.017 (3)0.003 (2)−0.024 (2)
C30.112 (3)0.099 (3)0.096 (3)−0.005 (3)−0.015 (3)−0.027 (3)
C40.116 (3)0.080 (3)0.111 (4)−0.016 (2)−0.005 (3)−0.015 (3)
C50.097 (3)0.080 (3)0.092 (3)−0.011 (2)0.003 (2)−0.001 (2)
C60.070 (2)0.069 (2)0.070 (2)−0.0040 (17)−0.0008 (17)−0.0007 (17)
C70.066 (2)0.070 (2)0.060 (2)0.0028 (17)0.0038 (15)0.0030 (16)
C80.070 (2)0.067 (2)0.076 (2)0.0049 (17)0.0110 (17)0.0075 (17)
C90.086 (3)0.126 (4)0.171 (4)0.035 (3)0.035 (3)0.065 (3)
C100.1334 (19)0.1375 (19)0.1356 (19)0.0024 (10)0.0091 (10)0.0072 (10)
C110.153 (5)0.165 (5)0.132 (5)0.029 (4)0.076 (4)0.063 (4)
C120.145 (5)0.131 (4)0.095 (4)0.007 (3)0.021 (3)0.047 (3)
C130.085 (3)0.114 (3)0.084 (3)0.004 (2)0.010 (2)0.030 (2)
C140.0672 (19)0.072 (2)0.0485 (18)0.0027 (17)0.0073 (15)−0.0005 (15)
C150.0619 (18)0.0671 (19)0.0464 (17)0.0090 (16)0.0051 (13)−0.0028 (14)
C160.069 (2)0.078 (2)0.0472 (18)0.0135 (18)0.0011 (15)0.0014 (15)
C170.110 (3)0.104 (3)0.0447 (19)0.004 (3)0.0011 (19)−0.0018 (18)
C180.115 (3)0.112 (3)0.063 (3)0.003 (3)−0.008 (2)−0.021 (2)
C190.098 (3)0.097 (3)0.076 (3)−0.011 (2)−0.001 (2)−0.017 (2)
C200.080 (2)0.088 (2)0.058 (2)0.005 (2)0.0109 (17)−0.0070 (18)

Geometric parameters (Å, °)

N1—C71.289 (4)C8—C131.380 (5)
N1—N21.370 (3)C9—C101.390 (7)
N2—C141.347 (4)C9—H90.9300
N2—H2B0.8600C10—C111.382 (8)
O1—C141.230 (4)C10—H100.9300
O2—C161.361 (4)C11—C121.336 (7)
O2—H2A0.8200C11—H110.9300
C1—C21.365 (5)C12—C131.387 (6)
C1—C61.380 (5)C12—H120.9300
C1—H10.9300C13—H130.9300
C2—C31.365 (6)C14—C151.484 (4)
C2—H20.9300C15—C201.387 (5)
C3—C41.345 (6)C15—C161.401 (4)
C3—H30.9300C16—C171.382 (5)
C4—C51.384 (6)C17—C181.354 (6)
C4—H40.9300C17—H170.9300
C5—C61.381 (5)C18—C191.372 (5)
C5—H50.9300C18—H180.9300
C6—C71.472 (4)C19—C201.369 (5)
C7—C81.481 (4)C19—H190.9300
C8—C91.360 (5)C20—H200.9300
C7—N1—N2116.7 (3)C11—C10—H10120.3
C14—N2—N1120.3 (2)C9—C10—H10120.3
C14—N2—H2B119.9C12—C11—C10121.2 (5)
N1—N2—H2B119.9C12—C11—H11119.4
C16—O2—H2A109.5C10—C11—H11119.4
C2—C1—C6121.0 (4)C11—C12—C13118.8 (5)
C2—C1—H1119.5C11—C12—H12120.6
C6—C1—H1119.5C13—C12—H12120.6
C1—C2—C3120.5 (4)C8—C13—C12121.4 (4)
C1—C2—H2119.7C8—C13—H13119.3
C3—C2—H2119.7C12—C13—H13119.3
C4—C3—C2119.6 (4)O1—C14—N2121.7 (3)
C4—C3—H3120.2O1—C14—C15120.9 (3)
C2—C3—H3120.2N2—C14—C15117.4 (3)
C3—C4—C5120.7 (4)C20—C15—C16117.1 (3)
C3—C4—H4119.6C20—C15—C14117.0 (3)
C5—C4—H4119.6C16—C15—C14125.8 (3)
C6—C5—C4120.3 (4)O2—C16—C17121.1 (3)
C6—C5—H5119.9O2—C16—C15119.2 (3)
C4—C5—H5119.9C17—C16—C15119.7 (3)
C1—C6—C5117.8 (3)C18—C17—C16121.1 (4)
C1—C6—C7121.8 (3)C18—C17—H17119.5
C5—C6—C7120.4 (3)C16—C17—H17119.5
N1—C7—C6117.3 (3)C17—C18—C19120.6 (4)
N1—C7—C8123.2 (3)C17—C18—H18119.7
C6—C7—C8119.5 (3)C19—C18—H18119.7
C9—C8—C13118.9 (4)C20—C19—C18118.8 (4)
C9—C8—C7121.6 (4)C20—C19—H19120.6
C13—C8—C7119.4 (3)C18—C19—H19120.6
C8—C9—C10119.9 (5)C19—C20—C15122.6 (3)
C8—C9—H9120.0C19—C20—H20118.7
C10—C9—H9120.0C15—C20—H20118.7
C11—C10—C9119.5 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2B···O20.861.952.635 (3)136
O2—H2A···O1i0.821.872.688 (3)172

Symmetry codes: (i) −y+3/4, x+1/4, z+1/4.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2128).

References

  • Chang, J.-G. (2008). Acta Cryst. E64, o198. [PMC free article] [PubMed]
  • Huo, L.-H., Gao, S., Zhao, H., Zhao, J.-G., Zain, S. M. & Ng, S. W. (2004). Acta Cryst. E60, o1538–o1540.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

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