N'-Diphenyl-methyl-ene-2-hydroxy-benzohydrazide.

The title compound, C(20)H(16)N(2)O(2), was synthesized by the reaction of 2-hydroxy-benzohydrazide with diphenyl-methanone. The dihedral angle between the phenyl rings is 76.28 (11)°. The amino H atom is involved in an intra-molecular N-H⋯O hydrogen bond. In the crystal structure, the hydr-oxy groups and carbonyl O atoms form inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into chains running along the b axis.

Related literature

For general background to Schiff bases in coordination chemistry, see: Garnovskii et al. (1993 ▶); Musie et al. (2001 ▶); Paul et al. (2002 ▶); Anderson et al. (1997 ▶). For a related structure, see Ji & Shi (2008 ▶).

Experimental

Crystal data

C20H16N2O2

M = 316.35

Monoclinic,

a = 15.4057 (18) Å

b = 12.5179 (15) Å

c = 8.8445 (10) Å

β = 103.777 (2)°

V = 1656.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.988, T max = 0.992

8538 measured reflections

2934 independent reflections

1910 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.126

S = 1.05

2934 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.15 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809043530/cv2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809043530/cv2634Isup2.hkl

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

C20H16N2O2	F(000) = 664
Mr = 316.35	Dx = 1.268 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1519 reflections
a = 15.4057 (18) Å	θ = 2.7–21.7°
b = 12.5179 (15) Å	µ = 0.08 mm−1
c = 8.8445 (10) Å	T = 295 K
β = 103.777 (2)°	Block, colourless
V = 1656.6 (3) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	2934 independent reflections
Radiation source: fine-focus sealed tube	1910 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −18→16
Tmin = 0.988, Tmax = 0.992	k = −14→13
8538 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0607P)2 + 0.0637P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2934 reflections	Δρmax = 0.15 e Å−3
219 parameters	Δρmin = −0.15 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0070 (15)

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
O1	0.00834 (9)	0.02500 (10)	0.30160 (15)	0.0574 (4)
H1	−0.0088	−0.0359	0.3125	0.086*
O2	0.06286 (9)	0.32928 (10)	0.16995 (15)	0.0555 (4)
N1	0.12496 (10)	0.18665 (12)	0.30963 (18)	0.0502 (4)
H1A	0.1222	0.1197	0.3297	0.060*
N2	0.19612 (10)	0.24715 (12)	0.38673 (19)	0.0528 (4)
C8	0.26326 (12)	0.19876 (15)	0.4739 (2)	0.0482 (5)
C2	−0.01536 (12)	0.16611 (13)	0.1159 (2)	0.0422 (4)
C7	0.05922 (12)	0.23391 (14)	0.2017 (2)	0.0434 (5)
C9	0.27034 (12)	0.08062 (15)	0.4971 (2)	0.0484 (5)
C6	−0.10938 (12)	0.00942 (15)	0.0696 (2)	0.0502 (5)
H6	−0.1254	−0.0570	0.1016	0.060*
C1	−0.03865 (12)	0.06532 (14)	0.1631 (2)	0.0431 (5)
C15	0.34002 (12)	0.26687 (16)	0.5508 (2)	0.0520 (5)
C3	−0.06406 (13)	0.20669 (15)	−0.0252 (2)	0.0521 (5)
H3	−0.0496	0.2738	−0.0570	0.063*
C16	0.34477 (13)	0.37350 (16)	0.5095 (2)	0.0586 (6)
H16	0.2984	0.4033	0.4343	0.070*
C5	−0.15573 (13)	0.05148 (16)	−0.0693 (2)	0.0577 (5)
H5	−0.2029	0.0133	−0.1309	0.069*
C17	0.41724 (15)	0.43560 (19)	0.5786 (3)	0.0684 (6)
H17	0.4193	0.5068	0.5499	0.082*
C20	0.41002 (13)	0.22566 (19)	0.6647 (3)	0.0659 (6)
H20	0.4081	0.1548	0.6951	0.079*
C4	−0.13280 (14)	0.15061 (16)	−0.1188 (2)	0.0601 (6)
H4	−0.1636	0.1785	−0.2139	0.072*
C10	0.32717 (14)	0.02240 (18)	0.4281 (2)	0.0635 (6)
H10	0.3609	0.0570	0.3685	0.076*
C14	0.22226 (14)	0.02769 (16)	0.5863 (3)	0.0620 (6)
H14	0.1841	0.0658	0.6336	0.074*
C12	0.28481 (17)	−0.13853 (18)	0.5365 (3)	0.0733 (7)
H12	0.2891	−0.2123	0.5489	0.088*
C13	0.23000 (16)	−0.08149 (18)	0.6065 (3)	0.0746 (7)
H13	0.1977	−0.1163	0.6682	0.089*
C18	0.48636 (16)	0.3929 (2)	0.6896 (3)	0.0767 (7)
H18	0.5356	0.4347	0.7348	0.092*
C11	0.33363 (16)	−0.08721 (19)	0.4479 (3)	0.0739 (7)
H11	0.3713	−0.1262	0.4008	0.089*
C19	0.48253 (15)	0.2882 (2)	0.7335 (3)	0.0791 (7)
H19	0.5288	0.2593	0.8098	0.095*

	U11	U22	U33	U12	U13	U23
O1	0.0607 (9)	0.0447 (8)	0.0559 (9)	−0.0078 (7)	−0.0078 (7)	0.0078 (7)
O2	0.0594 (9)	0.0384 (7)	0.0623 (9)	−0.0028 (6)	0.0021 (7)	0.0022 (6)
N1	0.0429 (9)	0.0383 (8)	0.0611 (10)	−0.0037 (7)	−0.0043 (8)	0.0002 (8)
N2	0.0446 (9)	0.0491 (9)	0.0586 (10)	−0.0067 (8)	0.0000 (8)	−0.0011 (8)
C8	0.0404 (11)	0.0523 (11)	0.0488 (11)	−0.0012 (9)	0.0042 (9)	0.0004 (9)
C2	0.0399 (10)	0.0395 (10)	0.0448 (11)	0.0032 (8)	0.0056 (8)	−0.0019 (8)
C7	0.0413 (10)	0.0396 (11)	0.0472 (11)	0.0028 (9)	0.0059 (9)	−0.0006 (9)
C9	0.0382 (10)	0.0516 (11)	0.0494 (12)	0.0018 (9)	−0.0011 (9)	−0.0013 (9)
C6	0.0461 (11)	0.0439 (11)	0.0562 (12)	−0.0032 (9)	0.0038 (10)	−0.0039 (9)
C1	0.0422 (10)	0.0405 (10)	0.0433 (11)	0.0032 (8)	0.0034 (9)	−0.0025 (8)
C15	0.0426 (11)	0.0608 (13)	0.0500 (12)	−0.0057 (10)	0.0055 (9)	−0.0017 (10)
C3	0.0526 (12)	0.0480 (11)	0.0514 (12)	0.0015 (9)	0.0038 (10)	0.0028 (9)
C16	0.0492 (12)	0.0623 (13)	0.0614 (14)	−0.0066 (11)	0.0078 (10)	0.0012 (11)
C5	0.0510 (12)	0.0580 (13)	0.0564 (13)	−0.0049 (10)	−0.0025 (10)	−0.0116 (11)
C17	0.0616 (14)	0.0704 (14)	0.0731 (16)	−0.0205 (12)	0.0156 (13)	−0.0029 (12)
C20	0.0542 (13)	0.0691 (14)	0.0652 (14)	−0.0085 (11)	−0.0041 (11)	0.0014 (11)
C4	0.0604 (13)	0.0600 (13)	0.0493 (12)	0.0007 (11)	−0.0078 (10)	0.0012 (10)
C10	0.0580 (14)	0.0745 (15)	0.0561 (13)	0.0080 (12)	0.0096 (11)	−0.0011 (12)
C14	0.0535 (13)	0.0533 (12)	0.0791 (15)	0.0034 (10)	0.0157 (11)	0.0031 (11)
C12	0.0687 (16)	0.0562 (14)	0.0826 (17)	0.0063 (12)	−0.0065 (14)	−0.0007 (13)
C13	0.0647 (15)	0.0598 (14)	0.0981 (19)	−0.0009 (12)	0.0170 (14)	0.0087 (13)
C18	0.0557 (15)	0.0946 (19)	0.0743 (16)	−0.0265 (14)	0.0043 (13)	−0.0112 (14)
C11	0.0684 (16)	0.0753 (16)	0.0708 (16)	0.0239 (13)	0.0021 (13)	−0.0180 (13)
C19	0.0538 (14)	0.0948 (19)	0.0756 (17)	−0.0127 (13)	−0.0108 (12)	−0.0011 (14)

O1—C1	1.363 (2)	C16—C17	1.378 (3)
O1—H1	0.8200	C16—H16	0.9300
O2—C7	1.231 (2)	C5—C4	1.389 (3)
N1—C7	1.352 (2)	C5—H5	0.9300
N1—N2	1.373 (2)	C17—C18	1.373 (3)
N1—H1A	0.8600	C17—H17	0.9300
N2—C8	1.285 (2)	C20—C19	1.381 (3)
C8—C15	1.485 (3)	C20—H20	0.9300
C8—C9	1.493 (3)	C4—H4	0.9300
C2—C3	1.390 (3)	C10—C11	1.384 (3)
C2—C1	1.402 (2)	C10—H10	0.9300
C2—C7	1.483 (2)	C14—C13	1.380 (3)
C9—C14	1.374 (3)	C14—H14	0.9300
C9—C10	1.388 (3)	C12—C13	1.362 (3)
C6—C5	1.371 (3)	C12—C11	1.369 (3)
C6—C1	1.390 (3)	C12—H12	0.9300
C6—H6	0.9300	C13—H13	0.9300
C15—C20	1.388 (3)	C18—C19	1.372 (3)
C15—C16	1.390 (3)	C18—H18	0.9300
C3—C4	1.372 (3)	C11—H11	0.9300
C3—H3	0.9300	C19—H19	0.9300
C1—O1—H1	109.5	C6—C5—H5	119.7
C7—N1—N2	119.00 (15)	C4—C5—H5	119.7
C7—N1—H1A	120.5	C18—C17—C16	120.4 (2)
N2—N1—H1A	120.5	C18—C17—H17	119.8
C8—N2—N1	118.12 (16)	C16—C17—H17	119.8
N2—C8—C15	116.33 (17)	C19—C20—C15	121.1 (2)
N2—C8—C9	124.85 (17)	C19—C20—H20	119.5
C15—C8—C9	118.78 (16)	C15—C20—H20	119.5
C3—C2—C1	118.30 (17)	C3—C4—C5	118.98 (19)
C3—C2—C7	115.88 (16)	C3—C4—H4	120.5
C1—C2—C7	125.80 (16)	C5—C4—H4	120.5
O2—C7—N1	121.23 (17)	C11—C10—C9	119.9 (2)
O2—C7—C2	120.69 (16)	C11—C10—H10	120.0
N1—C7—C2	118.00 (16)	C9—C10—H10	120.0
C14—C9—C10	118.84 (19)	C9—C14—C13	120.7 (2)
C14—C9—C8	121.65 (17)	C9—C14—H14	119.7
C10—C9—C8	119.51 (18)	C13—C14—H14	119.7
C5—C6—C1	120.47 (18)	C13—C12—C11	119.9 (2)
C5—C6—H6	119.8	C13—C12—H12	120.0
C1—C6—H6	119.8	C11—C12—H12	120.0
O1—C1—C6	121.44 (16)	C12—C13—C14	120.3 (2)
O1—C1—C2	118.79 (16)	C12—C13—H13	119.9
C6—C1—C2	119.76 (17)	C14—C13—H13	119.9
C20—C15—C16	117.83 (19)	C19—C18—C17	119.7 (2)
C20—C15—C8	121.03 (18)	C19—C18—H18	120.1
C16—C15—C8	121.13 (18)	C17—C18—H18	120.1
C4—C3—C2	121.93 (18)	C12—C11—C10	120.4 (2)
C4—C3—H3	119.0	C12—C11—H11	119.8
C2—C3—H3	119.0	C10—C11—H11	119.8
C17—C16—C15	120.9 (2)	C18—C19—C20	120.1 (2)
C17—C16—H16	119.6	C18—C19—H19	120.0
C15—C16—H16	119.6	C20—C19—H19	120.0
C6—C5—C4	120.55 (19)
C7—N1—N2—C8	−171.19 (17)	C9—C8—C15—C16	167.06 (18)
N1—N2—C8—C15	177.98 (15)	C1—C2—C3—C4	−0.7 (3)
N1—N2—C8—C9	0.5 (3)	C7—C2—C3—C4	177.72 (17)
N2—N1—C7—O2	1.2 (3)	C20—C15—C16—C17	0.7 (3)
N2—N1—C7—C2	177.88 (15)	C8—C15—C16—C17	−178.39 (18)
C3—C2—C7—O2	17.5 (3)	C1—C6—C5—C4	−0.1 (3)
C1—C2—C7—O2	−164.16 (17)	C15—C16—C17—C18	0.2 (3)
C3—C2—C7—N1	−159.20 (16)	C16—C15—C20—C19	−0.7 (3)
C1—C2—C7—N1	19.1 (3)	C8—C15—C20—C19	178.36 (19)
N2—C8—C9—C14	−73.8 (3)	C2—C3—C4—C5	1.6 (3)
C15—C8—C9—C14	108.8 (2)	C6—C5—C4—C3	−1.2 (3)
N2—C8—C9—C10	106.6 (2)	C14—C9—C10—C11	0.9 (3)
C15—C8—C9—C10	−70.8 (2)	C8—C9—C10—C11	−179.48 (19)
C5—C6—C1—O1	180.00 (17)	C10—C9—C14—C13	−0.3 (3)
C5—C6—C1—C2	0.9 (3)	C8—C9—C14—C13	−179.9 (2)
C3—C2—C1—O1	−179.66 (16)	C11—C12—C13—C14	1.1 (4)
C7—C2—C1—O1	2.1 (3)	C9—C14—C13—C12	−0.8 (4)
C3—C2—C1—C6	−0.5 (3)	C16—C17—C18—C19	−1.0 (4)
C7—C2—C1—C6	−178.80 (16)	C13—C12—C11—C10	−0.5 (4)
N2—C8—C15—C20	170.39 (19)	C9—C10—C11—C12	−0.6 (3)
C9—C8—C15—C20	−12.0 (3)	C17—C18—C19—C20	1.0 (4)
N2—C8—C15—C16	−10.6 (3)	C15—C20—C19—C18	−0.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2i	0.82	1.90	2.7204 (17)	173
N1—H1A···O1	0.86	2.08	2.696 (2)	128

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2i	0.82	1.90	2.7204 (17)	173
N1—H1A⋯O1	0.86	2.08	2.696 (2)	128

Symmetry code: (i) .