N'-(2-Hy-droxy-1,2-diphenyl-ethyl-idene)benzohydrazide.

In the title compound, C(21)H(18)N(2)O(2), the amino group is involved in an intra-molecular N-H⋯O hydrogen bond. The rings make dihedral angles of 37.9 (2), 64.4 (2) and 83.6 (2)°. In the crystal, inter-molecular O-H⋯N and O-H⋯O hydrogen bonds link the mol-ecules 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 = 330.37

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.07

1729 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.16 e Å−3

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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810038365/cv2764sup1.cif

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

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

C21H18N2O2	Dx = 1.300 Mg m−3
Mr = 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

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

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(Fo2) + (0.0315P)2 + 0.2666P] where P = (Fo2 + 2Fc2)/3
1729 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.14 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) .