N′-(Diphenyl­methyl­ene)-2-hydroxy­benzo­hydrazide

Li, Y.; Chen, C.; Yang, R.; Zhao, R.

doi:10.1107/S1600536809006916

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o659

doi:10.1107/S1600536809006916

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N′-(Diphenylmethylene)-2-hydroxybenzohydrazide

Yanfei Li,^a ^* Chunhua Chen,^b Rongdong Yang ^a and Rengao Zhao ^a

^aDepartment of Materials and Chemical Engineering, Taishan University, 271021 Taian, Shandong, People's Republic of China, and ^bNo. 1 Middle School of Qufu, 273100, Shandong, People's Republic of China
^*Correspondence e-mail: klsz79@163.com

(Received 10 January 2009; accepted 25 February 2009; online 6 March 2009)

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 ); Huo et al. (2004 ).

Experimental

Crystal data

C₂₀H₁₆N₂O₂
M_r = 316.35
Tetragonal, I 4₁ /a
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 ) 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[F² > 2σ(F²)] = 0.072
wR(F²) = 0.255
S = 1.01
2929 reflections
217 parameters
7 restraints
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2	0.86	1.95	2.635 (3)	136
O2—H2A⋯O1ⁱ	0.82	1.87	2.688 (3)	172
Symmetry code: (i) $[-y+{\script{3\over 4}}, x+{\script{1\over 4}}, z+{\script{1\over 4}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

For the coordination environment of this molecule, see: Chang (2008); Huo et al. (2004).

Experimental top

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.

Computing details top

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

Figures top

	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.

N'-(Diphenylmethylene)-2-hydroxybenzohydrazide top

Crystal data top

C₂₀H₁₆N₂O₂	D_x = 1.263 Mg m⁻³
M_r = 316.35	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 3007 reflections
Hall symbol: -I 4ad	θ = 2.4–20.0°
a = 16.5157 (9) Å	µ = 0.08 mm⁻¹
c = 24.401 (3) Å	T = 273 K
V = 6655.8 (10) Å³	Block, colourless
Z = 16	0.31 × 0.25 × 0.19 mm
F(000) = 2672

Data collection top

Bruker SMART CCD area-detector diffractometer	2929 independent reflections
Radiation source: Fine–focus sealed tube	1610 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.096
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→17
T_min = 0.972, T_max = 0.987	k = −19→19
17393 measured reflections	l = −24→28

Refinement top

Refinement on F²	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F² > 2σ(F²)] = 0.072	Hydrogen site location: Geom
wR(F²) = 0.255	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.158P)² + 0.5238P] where P = (F_o² + 2F_c²)/3
2929 reflections	(Δ/σ)_max = 0.001
217 parameters	Δρ_max = 0.53 e Å⁻³
7 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₀H₁₆N₂O₂	Z = 16
M_r = 316.35	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.08 mm⁻¹
a = 16.5157 (9) Å	T = 273 K
c = 24.401 (3) Å	0.31 × 0.25 × 0.19 mm
V = 6655.8 (10) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	2929 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1610 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.987	R_int = 0.096
17393 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.072	7 restraints
wR(F²) = 0.255	H-atom parameters constrained
S = 1.01	Δρ_max = 0.53 e Å⁻³
2929 reflections	Δρ_min = −0.47 e Å⁻³
217 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
N1	0.19770 (16)	0.48883 (16)	0.91131 (10)	0.0673 (8)
N2	0.20636 (16)	0.53442 (16)	0.95782 (10)	0.0660 (8)
H2B	0.1828	0.5197	0.9876	0.079*
O1	0.28234 (15)	0.62777 (14)	0.91455 (9)	0.0834 (8)
O2	0.18133 (14)	0.55740 (15)	1.06333 (8)	0.0770 (7)
H2A	0.1681	0.5493	1.0953	0.115*
C1	0.1847 (2)	0.3933 (2)	0.81748 (16)	0.0892 (12)
H1	0.2122	0.4422	0.8148	0.107*
C2	0.1798 (3)	0.3438 (3)	0.77280 (18)	0.1029 (13)
H2	0.2036	0.3596	0.7399	0.123*
C3	0.1404 (3)	0.2713 (3)	0.7760 (2)	0.1021 (14)
H3	0.1382	0.2373	0.7456	0.123*
C4	0.1046 (3)	0.2494 (3)	0.8232 (2)	0.1024 (14)
H4	0.0765	0.2007	0.8251	0.123*
C5	0.1094 (2)	0.2984 (2)	0.86910 (18)	0.0894 (12)
H5	0.0855	0.2819	0.9018	0.107*
C6	0.1494 (2)	0.3717 (2)	0.86662 (14)	0.0696 (9)
C7	0.15649 (19)	0.4228 (2)	0.91578 (13)	0.0655 (9)
C8	0.1194 (2)	0.3957 (2)	0.96790 (14)	0.0708 (9)
C9	0.0389 (3)	0.4050 (3)	0.9779 (2)	0.1276 (19)
H9	0.0055	0.4280	0.9515	0.153*
C10	0.0067 (4)	0.3801 (3)	1.0278 (3)	0.1355 (17)
H10	−0.0488	0.3835	1.0341	0.163*
C11	0.0576 (4)	0.3502 (4)	1.0679 (2)	0.150 (2)
H11	0.0368	0.3385	1.1024	0.180*
C12	0.1362 (4)	0.3380 (3)	1.0581 (2)	0.1236 (18)
H12	0.1693	0.3145	1.0845	0.148*
C13	0.1676 (3)	0.3610 (3)	1.00770 (17)	0.0944 (13)
H13	0.2223	0.3528	1.0006	0.113*
C14	0.2516 (2)	0.6023 (2)	0.95709 (12)	0.0625 (8)
C15	0.26762 (18)	0.64251 (19)	1.01038 (12)	0.0585 (8)
C16	0.2366 (2)	0.6184 (2)	1.06129 (12)	0.0648 (9)
C17	0.2630 (3)	0.6562 (3)	1.10856 (14)	0.0864 (11)
H17	0.2436	0.6389	1.1423	0.104*
C18	0.3167 (3)	0.7181 (3)	1.10648 (16)	0.0967 (13)
H18	0.3334	0.7430	1.1388	0.116*
C19	0.3466 (2)	0.7445 (3)	1.05717 (16)	0.0904 (12)
H19	0.3830	0.7874	1.0557	0.108*
C20	0.3218 (2)	0.7066 (2)	1.01018 (14)	0.0752 (10)
H20	0.3422	0.7246	0.9768	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0836 (19)	0.0705 (17)	0.0477 (15)	−0.0095 (15)	0.0066 (13)	−0.0014 (12)
N2	0.0788 (18)	0.0773 (18)	0.0418 (14)	−0.0052 (14)	0.0106 (12)	0.0011 (12)
O1	0.1105 (19)	0.0922 (17)	0.0476 (13)	−0.0258 (14)	0.0190 (12)	−0.0067 (12)
O2	0.0928 (17)	0.0963 (17)	0.0417 (12)	−0.0020 (14)	0.0095 (11)	0.0066 (11)
C1	0.107 (3)	0.090 (3)	0.070 (3)	−0.021 (2)	0.003 (2)	−0.007 (2)
C2	0.128 (4)	0.108 (3)	0.073 (3)	−0.017 (3)	0.003 (2)	−0.024 (2)
C3	0.112 (3)	0.099 (3)	0.096 (3)	−0.005 (3)	−0.015 (3)	−0.027 (3)
C4	0.116 (3)	0.080 (3)	0.111 (4)	−0.016 (2)	−0.005 (3)	−0.015 (3)
C5	0.097 (3)	0.080 (3)	0.092 (3)	−0.011 (2)	0.003 (2)	−0.001 (2)
C6	0.070 (2)	0.069 (2)	0.070 (2)	−0.0040 (17)	−0.0008 (17)	−0.0007 (17)
C7	0.066 (2)	0.070 (2)	0.060 (2)	0.0028 (17)	0.0038 (15)	0.0030 (16)
C8	0.070 (2)	0.067 (2)	0.076 (2)	0.0049 (17)	0.0110 (17)	0.0075 (17)
C9	0.086 (3)	0.126 (4)	0.171 (4)	0.035 (3)	0.035 (3)	0.065 (3)
C10	0.1334 (19)	0.1375 (19)	0.1356 (19)	0.0024 (10)	0.0091 (10)	0.0072 (10)
C11	0.153 (5)	0.165 (5)	0.132 (5)	0.029 (4)	0.076 (4)	0.063 (4)
C12	0.145 (5)	0.131 (4)	0.095 (4)	0.007 (3)	0.021 (3)	0.047 (3)
C13	0.085 (3)	0.114 (3)	0.084 (3)	0.004 (2)	0.010 (2)	0.030 (2)
C14	0.0672 (19)	0.072 (2)	0.0485 (18)	0.0027 (17)	0.0073 (15)	−0.0005 (15)
C15	0.0619 (18)	0.0671 (19)	0.0464 (17)	0.0090 (16)	0.0051 (13)	−0.0028 (14)
C16	0.069 (2)	0.078 (2)	0.0472 (18)	0.0135 (18)	0.0011 (15)	0.0014 (15)
C17	0.110 (3)	0.104 (3)	0.0447 (19)	0.004 (3)	0.0011 (19)	−0.0018 (18)
C18	0.115 (3)	0.112 (3)	0.063 (3)	0.003 (3)	−0.008 (2)	−0.021 (2)
C19	0.098 (3)	0.097 (3)	0.076 (3)	−0.011 (2)	−0.001 (2)	−0.017 (2)
C20	0.080 (2)	0.088 (2)	0.058 (2)	0.005 (2)	0.0109 (17)	−0.0070 (18)

Geometric parameters (Å, º) top

N1—C7	1.289 (4)	C8—C13	1.380 (5)
N1—N2	1.370 (3)	C9—C10	1.390 (7)
N2—C14	1.347 (4)	C9—H9	0.9300
N2—H2B	0.8600	C10—C11	1.382 (8)
O1—C14	1.230 (4)	C10—H10	0.9300
O2—C16	1.361 (4)	C11—C12	1.336 (7)
O2—H2A	0.8200	C11—H11	0.9300
C1—C2	1.365 (5)	C12—C13	1.387 (6)
C1—C6	1.380 (5)	C12—H12	0.9300
C1—H1	0.9300	C13—H13	0.9300
C2—C3	1.365 (6)	C14—C15	1.484 (4)
C2—H2	0.9300	C15—C20	1.387 (5)
C3—C4	1.345 (6)	C15—C16	1.401 (4)
C3—H3	0.9300	C16—C17	1.382 (5)
C4—C5	1.384 (6)	C17—C18	1.354 (6)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.381 (5)	C18—C19	1.372 (5)
C5—H5	0.9300	C18—H18	0.9300
C6—C7	1.472 (4)	C19—C20	1.369 (5)
C7—C8	1.481 (4)	C19—H19	0.9300
C8—C9	1.360 (5)	C20—H20	0.9300

C7—N1—N2	116.7 (3)	C11—C10—H10	120.3
C14—N2—N1	120.3 (2)	C9—C10—H10	120.3
C14—N2—H2B	119.9	C12—C11—C10	121.2 (5)
N1—N2—H2B	119.9	C12—C11—H11	119.4
C16—O2—H2A	109.5	C10—C11—H11	119.4
C2—C1—C6	121.0 (4)	C11—C12—C13	118.8 (5)
C2—C1—H1	119.5	C11—C12—H12	120.6
C6—C1—H1	119.5	C13—C12—H12	120.6
C1—C2—C3	120.5 (4)	C8—C13—C12	121.4 (4)
C1—C2—H2	119.7	C8—C13—H13	119.3
C3—C2—H2	119.7	C12—C13—H13	119.3
C4—C3—C2	119.6 (4)	O1—C14—N2	121.7 (3)
C4—C3—H3	120.2	O1—C14—C15	120.9 (3)
C2—C3—H3	120.2	N2—C14—C15	117.4 (3)
C3—C4—C5	120.7 (4)	C20—C15—C16	117.1 (3)
C3—C4—H4	119.6	C20—C15—C14	117.0 (3)
C5—C4—H4	119.6	C16—C15—C14	125.8 (3)
C6—C5—C4	120.3 (4)	O2—C16—C17	121.1 (3)
C6—C5—H5	119.9	O2—C16—C15	119.2 (3)
C4—C5—H5	119.9	C17—C16—C15	119.7 (3)
C1—C6—C5	117.8 (3)	C18—C17—C16	121.1 (4)
C1—C6—C7	121.8 (3)	C18—C17—H17	119.5
C5—C6—C7	120.4 (3)	C16—C17—H17	119.5
N1—C7—C6	117.3 (3)	C17—C18—C19	120.6 (4)
N1—C7—C8	123.2 (3)	C17—C18—H18	119.7
C6—C7—C8	119.5 (3)	C19—C18—H18	119.7
C9—C8—C13	118.9 (4)	C20—C19—C18	118.8 (4)
C9—C8—C7	121.6 (4)	C20—C19—H19	120.6
C13—C8—C7	119.4 (3)	C18—C19—H19	120.6
C8—C9—C10	119.9 (5)	C19—C20—C15	122.6 (3)
C8—C9—H9	120.0	C19—C20—H20	118.7
C10—C9—H9	120.0	C15—C20—H20	118.7
C11—C10—C9	119.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.86	1.95	2.635 (3)	136
O2—H2A···O1ⁱ	0.82	1.87	2.688 (3)	172

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆N₂O₂
M_r	316.35
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	273
a, c (Å)	16.5157 (9), 24.401 (3)
V (Å³)	6655.8 (10)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.25 × 0.19

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.972, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17393, 2929, 1610
R_int	0.096
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.072, 0.255, 1.01
No. of reflections	2929
No. of parameters	217
No. of restraints	7
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.47

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2	0.86	1.95	2.635 (3)	135.8
O2—H2A···O1ⁱ	0.82	1.87	2.688 (3)	171.6

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

Acknowledgements

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

References

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