N′-(2-Hy­droxy-1,2-diphenyl­ethyl­idene)benzohydrazide

Song, M.

doi:10.1107/S1600536810038365

organic compounds

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Volume 66| Part 10| October 2010| Page o2692

doi:10.1107/S1600536810038365

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N′-(2-Hydroxy-1,2-diphenylethylidene)benzohydrazide

Ming-zhi Song ^a ^*

^aCollege of Chemistry and Chemical Technology, Binzhou University, Binzhou 256600, Shandong, People's Republic of China
^*Correspondence e-mail: fanchuangang2009@163.com

(Received 6 September 2010; accepted 25 September 2010; online 30 September 2010)

In the title compound, C₂₁H₁₈N₂O₂, the amino group is involved in an intramolecular N—H⋯O hydrogen bond. The rings make dihedral angles of 37.9 (2), 64.4 (2) and 83.6 (2)°. In the crystal, intermolecular O—H⋯N and O—H⋯O hydrogen bonds link the molecules into chains running along [100].

Related literature

For related structures, see: Fun et al.(2008 ); Nie (2008 ); Seijas et al. (2007 ). For general background to the biological activity of Schiff bases and their metal complexes, see: Chakraborty et al. (1996 ); Jeewoth et al. (1999 ).

Experimental

Crystal data

C₂₁H₁₈N₂O₂
M_r = 330.37
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.7318 (8) Å
b = 11.0653 (12) Å
c = 19.725 (2) Å
V = 1687.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.41 × 0.16 × 0.13 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ) T_min = 0.966, T_max = 0.989
7865 measured reflections
1729 independent reflections
1051 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.097
S = 1.07
1729 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.82	2.45	2.998 (4)	125
O2—H2⋯N2ⁱ	0.82	2.20	2.992 (4)	164
N1—H1⋯O2	0.86	2.12	2.715 (4)	126
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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/S1600536810038365/cv2764sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810038365/cv2764Isup2.hkl

checkCIF report

Comment top

Schiff bases and their metal complexes were reported to exhibit fungicidal, bactericidal, antiviral, and antitubercular activity (Chakraborty et al., 1996; Jeewoth et al., 1999). Herewith we present the title compound (I), which is a new Shiff base compound.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in similar compounds (Nie et al., 2008; Fun et al., 2008) The C=N (C8=N2) bond length in the molecule is 1.287 (3) Å. Two benzene rings - C2—C7 and C16—C21, respectively - form a dihedral angle of 37.94 (7) °. The amino group is involved in formation of intramolecular N—H···O hydrogen bond (Table 1), while intermolecular O—H···N and O—H···O hydrogen bonds (Table 1) link the molecules into chains running in direction [100].

Related literature top

For related structures, see: Fun et al.(2008); Nie (2008); Seijas et al. (2007). For general background to the biological activity of Schiff bases and their metal complexes, see: Chakraborty et al. (1996); Jeewoth et al. (1999).

Experimental top

Benzoin (5 mmol), benzohydrazide (5 mmol) and methanol (10 ml) were mixed in 50 ml flask. After stirring for 2 h at 373 K, the resulting mixture was recrystalized from methanol, affording the title compound as a colorless crystalline solid. Elemental analysis: calculated for C₂₁H₁₈N₂O₂: C 76.34, H 5.49, N 8.48%; found: C 76.21, H 5.56, N 8.54%.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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. lThe molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

N'-(2-Hydroxy-1,2-diphenylethylidene)benzohydrazide top

Crystal data top

C₂₁H₁₈N₂O₂	D_x = 1.300 Mg m⁻³
M_r = 330.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 1315 reflections
a = 7.7318 (8) Å	θ = 2.8–19.7°
b = 11.0653 (12) Å	µ = 0.09 mm⁻¹
c = 19.725 (2) Å	T = 298 K
V = 1687.5 (3) Å³	Needle, colourless
Z = 4	0.41 × 0.16 × 0.13 mm
F(000) = 696

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1729 independent reflections
Radiation source: fine-focus sealed tube	1051 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	h = −9→8
T_min = 0.966, T_max = 0.989	k = −13→13
7865 measured reflections	l = −10→23

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0315P)² + 0.2666P] where P = (F_o² + 2F_c²)/3
1729 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₁H₁₈N₂O₂	V = 1687.5 (3) Å³
M_r = 330.37	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.7318 (8) Å	µ = 0.09 mm⁻¹
b = 11.0653 (12) Å	T = 298 K
c = 19.725 (2) Å	0.41 × 0.16 × 0.13 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	1729 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	1051 reflections with I > 2σ(I)
T_min = 0.966, T_max = 0.989	R_int = 0.054
7865 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.07	Δρ_max = 0.14 e Å⁻³
1729 reflections	Δρ_min = −0.16 e Å⁻³
226 parameters

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

	x	y	z	U_iso*/U_eq
N1	0.6095 (4)	0.7285 (3)	0.07224 (14)	0.0466 (9)
H1	0.5711	0.6582	0.0833	0.056*
N2	0.6267 (4)	0.7612 (3)	0.00542 (16)	0.0445 (9)
O1	0.7060 (4)	0.9121 (2)	0.10546 (13)	0.0550 (8)
O2	0.3956 (3)	0.5524 (2)	0.02563 (13)	0.0547 (8)
H2	0.3161	0.5939	0.0110	0.082*
C1	0.6551 (5)	0.8107 (4)	0.1207 (2)	0.0441 (10)
C2	0.6408 (5)	0.7712 (3)	0.19238 (19)	0.0424 (10)
C3	0.5837 (6)	0.6586 (4)	0.2127 (2)	0.0538 (12)
H3	0.5485	0.6025	0.1805	0.065*
C4	0.5787 (6)	0.6288 (4)	0.2806 (2)	0.0634 (13)
H4	0.5385	0.5531	0.2939	0.076*
C5	0.6324 (6)	0.7097 (4)	0.3285 (2)	0.0638 (13)
H5	0.6309	0.6890	0.3742	0.077*
C6	0.6885 (7)	0.8213 (4)	0.3087 (2)	0.0666 (14)
H6	0.7230	0.8774	0.3410	0.080*
C7	0.6939 (5)	0.8510 (4)	0.2408 (2)	0.0543 (11)
H7	0.7344	0.9267	0.2279	0.065*
C8	0.5919 (5)	0.6798 (3)	−0.03926 (18)	0.0416 (10)
C9	0.5351 (5)	0.5513 (3)	−0.0227 (2)	0.0443 (10)
H9	0.4936	0.5132	−0.0645	0.053*
C10	0.6779 (5)	0.4743 (3)	0.00625 (18)	0.0404 (10)
C11	0.8474 (5)	0.4869 (3)	−0.0146 (2)	0.0513 (11)
H11	0.8759	0.5474	−0.0453	0.062*
C12	0.9764 (6)	0.4104 (4)	0.0096 (2)	0.0650 (13)
H12	1.0900	0.4197	−0.0050	0.078*
C13	0.9345 (7)	0.3213 (4)	0.0551 (2)	0.0692 (14)
H13	1.0199	0.2697	0.0714	0.083*
C14	0.7678 (7)	0.3084 (4)	0.0766 (3)	0.0781 (15)
H14	0.7401	0.2484	0.1077	0.094*
C15	0.6399 (6)	0.3839 (4)	0.0523 (2)	0.0622 (12)
H15	0.5267	0.3739	0.0672	0.075*
C16	0.6030 (5)	0.7188 (3)	−0.11073 (19)	0.0414 (10)
C17	0.6508 (6)	0.6403 (4)	−0.16168 (19)	0.0547 (11)
H17	0.6767	0.5604	−0.1512	0.066*
C18	0.6607 (6)	0.6793 (4)	−0.2285 (2)	0.0632 (13)
H18	0.6950	0.6262	−0.2624	0.076*
C19	0.6194 (6)	0.7971 (4)	−0.2443 (2)	0.0664 (14)
H19	0.6252	0.8235	−0.2890	0.080*
C20	0.5702 (6)	0.8749 (4)	−0.1946 (2)	0.0565 (12)
H20	0.5415	0.9543	−0.2053	0.068*
C21	0.5628 (5)	0.8365 (3)	−0.1283 (2)	0.0511 (11)
H21	0.5301	0.8907	−0.0947	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.062 (3)	0.0403 (18)	0.038 (2)	−0.0013 (18)	−0.0013 (18)	0.0009 (16)
N2	0.053 (2)	0.0448 (18)	0.0352 (18)	0.0040 (18)	0.0059 (17)	0.0001 (15)
O1	0.066 (2)	0.0506 (16)	0.0487 (17)	−0.0063 (15)	−0.0034 (16)	0.0039 (15)
O2	0.0445 (17)	0.0555 (16)	0.0642 (18)	−0.0006 (14)	0.0037 (16)	0.0091 (14)
C1	0.040 (2)	0.045 (3)	0.047 (3)	0.007 (2)	0.001 (2)	0.001 (2)
C2	0.040 (3)	0.050 (2)	0.037 (2)	0.001 (2)	0.000 (2)	0.005 (2)
C3	0.064 (3)	0.050 (3)	0.048 (3)	−0.004 (2)	−0.004 (2)	0.000 (2)
C4	0.074 (4)	0.064 (3)	0.052 (3)	−0.009 (3)	−0.001 (3)	0.015 (3)
C5	0.073 (4)	0.072 (3)	0.047 (3)	0.005 (3)	−0.001 (3)	0.012 (3)
C6	0.090 (4)	0.064 (3)	0.045 (3)	0.000 (3)	−0.003 (3)	−0.005 (2)
C7	0.060 (3)	0.054 (3)	0.050 (3)	−0.002 (2)	−0.005 (2)	0.000 (2)
C8	0.046 (3)	0.039 (2)	0.040 (2)	0.003 (2)	−0.001 (2)	−0.002 (2)
C9	0.043 (2)	0.047 (2)	0.043 (2)	−0.005 (2)	−0.002 (2)	0.000 (2)
C10	0.043 (2)	0.041 (2)	0.037 (2)	−0.0017 (19)	−0.006 (2)	−0.004 (2)
C11	0.051 (3)	0.045 (2)	0.057 (3)	−0.003 (2)	0.000 (3)	−0.002 (2)
C12	0.056 (3)	0.059 (3)	0.080 (3)	0.002 (3)	−0.012 (3)	−0.012 (3)
C13	0.067 (4)	0.063 (3)	0.078 (3)	0.015 (3)	−0.029 (3)	−0.003 (3)
C14	0.080 (4)	0.079 (4)	0.075 (3)	0.006 (3)	−0.013 (3)	0.028 (3)
C15	0.059 (3)	0.070 (3)	0.057 (3)	0.001 (3)	−0.002 (3)	0.018 (3)
C16	0.042 (3)	0.043 (2)	0.040 (2)	−0.001 (2)	0.004 (2)	0.000 (2)
C17	0.064 (3)	0.051 (2)	0.049 (2)	0.004 (3)	0.002 (2)	−0.002 (2)
C18	0.075 (3)	0.067 (3)	0.047 (3)	−0.014 (3)	0.007 (3)	−0.005 (3)
C19	0.070 (3)	0.084 (4)	0.045 (3)	−0.015 (3)	0.000 (3)	0.008 (3)
C20	0.064 (3)	0.056 (3)	0.049 (3)	−0.006 (3)	0.002 (2)	0.015 (2)
C21	0.057 (3)	0.049 (3)	0.047 (3)	−0.003 (2)	0.004 (2)	−0.003 (2)

Geometric parameters (Å, º) top

N1—C1	1.366 (4)	C10—C11	1.380 (5)
N1—N2	1.373 (4)	C10—C15	1.383 (5)
N1—H1	0.8600	C11—C12	1.392 (5)
N2—C8	1.288 (4)	C11—H11	0.9300
O1—C1	1.226 (4)	C12—C13	1.372 (6)
O2—C9	1.439 (4)	C12—H12	0.9300
O2—H2	0.8200	C13—C14	1.365 (7)
C1—C2	1.485 (5)	C13—H13	0.9300
C2—C7	1.365 (5)	C14—C15	1.379 (6)
C2—C3	1.381 (5)	C14—H14	0.9300
C3—C4	1.380 (5)	C15—H15	0.9300
C3—H3	0.9300	C16—C17	1.379 (5)
C4—C5	1.366 (5)	C16—C21	1.383 (5)
C4—H4	0.9300	C17—C18	1.389 (5)
C5—C6	1.366 (6)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.378 (6)
C6—C7	1.378 (5)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.359 (5)
C7—H7	0.9300	C19—H19	0.9300
C8—C16	1.477 (5)	C20—C21	1.375 (5)
C8—C9	1.524 (5)	C20—H20	0.9300
C9—C10	1.507 (5)	C21—H21	0.9300
C9—H9	0.9800

C1—N1—N2	118.1 (3)	C11—C10—C9	121.7 (3)
C1—N1—H1	121.0	C15—C10—C9	120.1 (4)
N2—N1—H1	121.0	C10—C11—C12	121.1 (4)
C8—N2—N1	116.9 (3)	C10—C11—H11	119.4
C9—O2—H2	109.5	C12—C11—H11	119.4
O1—C1—N1	121.4 (4)	C13—C12—C11	119.4 (4)
O1—C1—C2	121.8 (4)	C13—C12—H12	120.3
N1—C1—C2	116.8 (4)	C11—C12—H12	120.3
C7—C2—C3	118.4 (4)	C14—C13—C12	120.1 (4)
C7—C2—C1	117.0 (3)	C14—C13—H13	120.0
C3—C2—C1	124.5 (4)	C12—C13—H13	120.0
C4—C3—C2	120.4 (4)	C13—C14—C15	120.4 (4)
C4—C3—H3	119.8	C13—C14—H14	119.8
C2—C3—H3	119.8	C15—C14—H14	119.8
C5—C4—C3	120.3 (4)	C14—C15—C10	120.9 (4)
C5—C4—H4	119.8	C14—C15—H15	119.6
C3—C4—H4	119.8	C10—C15—H15	119.6
C4—C5—C6	119.5 (4)	C17—C16—C21	118.1 (4)
C4—C5—H5	120.3	C17—C16—C8	121.8 (3)
C6—C5—H5	120.3	C21—C16—C8	120.1 (3)
C5—C6—C7	120.2 (4)	C16—C17—C18	120.7 (4)
C5—C6—H6	119.9	C16—C17—H17	119.7
C7—C6—H6	119.9	C18—C17—H17	119.7
C2—C7—C6	121.1 (4)	C19—C18—C17	119.7 (4)
C2—C7—H7	119.5	C19—C18—H18	120.1
C6—C7—H7	119.5	C17—C18—H18	120.1
N2—C8—C16	115.9 (3)	C20—C19—C18	120.1 (4)
N2—C8—C9	124.4 (3)	C20—C19—H19	120.0
C16—C8—C9	119.6 (3)	C18—C19—H19	120.0
O2—C9—C10	107.7 (3)	C19—C20—C21	120.1 (4)
O2—C9—C8	110.5 (3)	C19—C20—H20	120.0
C10—C9—C8	113.5 (3)	C21—C20—H20	120.0
O2—C9—H9	108.4	C20—C21—C16	121.3 (4)
C10—C9—H9	108.4	C20—C21—H21	119.3
C8—C9—H9	108.4	C16—C21—H21	119.3
C11—C10—C15	118.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.82	2.45	2.998 (4)	125
O2—H2···N2ⁱ	0.82	2.20	2.992 (4)	164
N1—H1···O2	0.86	2.12	2.715 (4)	126

Symmetry code: (i) x−1/2, −y+3/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O₂
M_r	330.37
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.7318 (8), 11.0653 (12), 19.725 (2)
V (Å³)	1687.5 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.41 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2007)
T_min, T_max	0.966, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	7865, 1729, 1051
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.097, 1.07
No. of reflections	1729
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), 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
O2—H2···O1ⁱ	0.82	2.45	2.998 (4)	125.2
O2—H2···N2ⁱ	0.82	2.20	2.992 (4)	163.9
N1—H1···O2	0.86	2.12	2.715 (4)	125.7

Symmetry code: (i) x−1/2, −y+3/2, −z.

Acknowledgements

The author acknowledges financial support by the Foundation of Binzhou University (grant No. BZXYQNLG2005013).

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