2-[(E)-Phen-yl(2-phenyl-hydrazin-1-yl-idene)meth-yl]phenol.

In the title hydrazone derivative, C(19)H(16)N(2)O, a twist is found between the hy-droxy-phenyl and N-bound phenyl rings [dihedral angle = 24.37 (7)°]. The C-bound phenyl ring is almost perpendicular to each of these planes [dihedral angles = 75.30 (7) and 86.00 (7)°, respectively]. The conformation about the imine bond [1.2935 (17) Å] is E. The hy-droxy group forms an intra-molecular hydrogen bond with the imine N atom. Zigzag chains along [001] mediated by N-H⋯O hydrogen bonds feature in the crystal packing.

Related literature

For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Wardell et al. (2007 ▶); Baddeley, de Souza França et al. (2009 ▶); Baddeley, Howie et al. (2009 ▶); de Souza et al. (2010 ▶); Howie, da Silva Lima et al. (2010 ▶); Howie, de Souza et al. (2010 ▶); Nogueira et al. (2011 ▶); Howie et al. (2011 ▶).

Experimental

Crystal data

C19H16N2O

M = 288.34

Monoclinic,

a = 9.6796 (3) Å

b = 15.3312 (5) Å

c = 10.3593 (2) Å

β = 108.149 (2)°

V = 1460.84 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 120 K

0.49 × 0.38 × 0.18 mm

Data collection

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.857, T max = 0.985

16532 measured reflections

3337 independent reflections

2624 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.141

S = 1.06

3337 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.40 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812005387/bt5814sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812005387/bt5814Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812005387/bt5814Isup3.cml

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

C19H16N2O	F(000) = 608
Mr = 288.34	Dx = 1.311 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9588 reflections
a = 9.6796 (3) Å	θ = 2.9–27.5°
b = 15.3312 (5) Å	µ = 0.08 mm−1
c = 10.3593 (2) Å	T = 120 K
β = 108.149 (2)°	Slab, yellow
V = 1460.84 (7) Å3	0.49 × 0.38 × 0.18 mm
Z = 4

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	3337 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode	2624 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 3.4°
φ and ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −19→19
Tmin = 0.857, Tmax = 0.985	l = −13→13
16532 measured reflections

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0846P)2 + 0.1552P] where P = (Fo2 + 2Fc2)/3
3337 reflections	(Δ/σ)max < 0.001
205 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.40 e Å−3

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 > 2σ(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	0.55543 (11)	0.62061 (7)	0.67432 (9)	0.0305 (3)
H1O	0.5167 (19)	0.6457 (11)	0.5981 (12)	0.046*
N1	0.49781 (12)	0.67646 (7)	0.42953 (11)	0.0245 (3)
N2	0.42408 (13)	0.73657 (8)	0.33672 (11)	0.0279 (3)
H2N	0.4722 (16)	0.7602 (10)	0.2854 (14)	0.033*
C1	0.68370 (14)	0.57283 (9)	0.51935 (12)	0.0219 (3)
C2	0.65661 (15)	0.56890 (9)	0.64615 (13)	0.0245 (3)
C3	0.73482 (15)	0.51112 (9)	0.74555 (13)	0.0275 (3)
H3	0.7182	0.5098	0.8312	0.033*
C4	0.83577 (16)	0.45602 (9)	0.72145 (14)	0.0294 (3)
H4	0.8872	0.4163	0.7900	0.035*
C5	0.86344 (16)	0.45784 (9)	0.59745 (14)	0.0268 (3)
H5	0.9333	0.4196	0.5808	0.032*
C6	0.78782 (15)	0.51608 (9)	0.49900 (13)	0.0245 (3)
H6	0.8073	0.5176	0.4146	0.029*
C7	0.60591 (14)	0.63406 (8)	0.41159 (12)	0.0225 (3)
C8	0.65557 (15)	0.64475 (9)	0.28938 (13)	0.0233 (3)
C9	0.57166 (16)	0.61134 (10)	0.16460 (13)	0.0295 (3)
H9	0.4805	0.5848	0.1559	0.035*
C10	0.62186 (17)	0.61703 (10)	0.05272 (14)	0.0332 (4)
H10	0.5659	0.5929	−0.0319	0.040*
C11	0.75214 (18)	0.65735 (10)	0.06393 (14)	0.0342 (4)
H11	0.7858	0.6608	−0.0128	0.041*
C12	0.83445 (17)	0.69288 (10)	0.18688 (15)	0.0331 (4)
H12	0.9230	0.7221	0.1939	0.040*
C13	0.78680 (16)	0.68548 (9)	0.29963 (14)	0.0286 (3)
H13	0.8444	0.7084	0.3845	0.034*
C14	0.31426 (15)	0.78382 (9)	0.36540 (12)	0.0246 (3)
C15	0.26578 (17)	0.86137 (10)	0.29652 (14)	0.0335 (4)
H15	0.3084	0.8820	0.2312	0.040*
C16	0.15586 (17)	0.90856 (11)	0.32279 (15)	0.0362 (4)
H16	0.1232	0.9613	0.2749	0.043*
C17	0.09268 (16)	0.87973 (10)	0.41823 (14)	0.0319 (4)
H17	0.0173	0.9124	0.4362	0.038*
C18	0.14125 (15)	0.80271 (10)	0.48685 (14)	0.0282 (3)
H18	0.0990	0.7827	0.5528	0.034*
C19	0.25048 (15)	0.75439 (9)	0.46098 (13)	0.0253 (3)
H19	0.2820	0.7013	0.5082	0.030*

	U11	U22	U33	U12	U13	U23
O1	0.0325 (6)	0.0394 (6)	0.0258 (5)	0.0046 (4)	0.0178 (4)	−0.0006 (4)
N1	0.0247 (6)	0.0277 (6)	0.0239 (5)	0.0032 (5)	0.0118 (5)	0.0002 (4)
N2	0.0281 (7)	0.0352 (7)	0.0262 (6)	0.0094 (5)	0.0171 (5)	0.0058 (5)
C1	0.0214 (7)	0.0247 (7)	0.0218 (6)	−0.0030 (5)	0.0098 (5)	−0.0021 (5)
C2	0.0230 (7)	0.0287 (7)	0.0250 (6)	−0.0044 (5)	0.0122 (5)	−0.0049 (5)
C3	0.0298 (8)	0.0326 (8)	0.0222 (6)	−0.0068 (6)	0.0112 (5)	−0.0002 (6)
C4	0.0298 (8)	0.0279 (7)	0.0299 (7)	−0.0031 (6)	0.0086 (6)	0.0047 (6)
C5	0.0258 (7)	0.0236 (7)	0.0329 (7)	0.0014 (5)	0.0117 (6)	−0.0011 (6)
C6	0.0265 (7)	0.0251 (7)	0.0246 (6)	−0.0029 (5)	0.0120 (5)	−0.0025 (5)
C7	0.0225 (7)	0.0250 (7)	0.0229 (6)	−0.0002 (5)	0.0115 (5)	−0.0020 (5)
C8	0.0250 (7)	0.0248 (7)	0.0238 (6)	0.0054 (5)	0.0130 (5)	0.0016 (5)
C9	0.0269 (8)	0.0367 (8)	0.0272 (7)	0.0016 (6)	0.0120 (6)	−0.0014 (6)
C10	0.0355 (9)	0.0428 (9)	0.0235 (7)	0.0085 (7)	0.0124 (6)	0.0001 (6)
C11	0.0452 (9)	0.0344 (8)	0.0323 (7)	0.0119 (7)	0.0256 (7)	0.0080 (6)
C12	0.0353 (9)	0.0301 (8)	0.0442 (8)	0.0019 (6)	0.0274 (7)	0.0032 (6)
C13	0.0286 (8)	0.0283 (7)	0.0330 (7)	0.0018 (6)	0.0156 (6)	−0.0020 (6)
C14	0.0225 (7)	0.0314 (7)	0.0218 (6)	0.0029 (6)	0.0094 (5)	−0.0035 (5)
C15	0.0356 (9)	0.0429 (9)	0.0278 (7)	0.0102 (7)	0.0181 (6)	0.0083 (6)
C16	0.0359 (9)	0.0428 (9)	0.0347 (8)	0.0160 (7)	0.0180 (7)	0.0112 (7)
C17	0.0266 (8)	0.0409 (9)	0.0320 (7)	0.0093 (6)	0.0147 (6)	0.0006 (6)
C18	0.0254 (8)	0.0346 (8)	0.0291 (7)	−0.0012 (6)	0.0151 (6)	−0.0023 (6)
C19	0.0248 (7)	0.0263 (7)	0.0271 (7)	−0.0004 (5)	0.0114 (6)	−0.0007 (5)

O1—C2	1.3605 (17)	C9—C10	1.3920 (19)
O1—H1O	0.853 (9)	C9—H9	0.9500
N1—C7	1.2935 (17)	C10—C11	1.376 (2)
N1—N2	1.3621 (16)	C10—H10	0.9500
N2—C14	1.3928 (17)	C11—C12	1.386 (2)
N2—H2N	0.886 (9)	C11—H11	0.9500
C1—C6	1.3963 (19)	C12—C13	1.3875 (19)
C1—C2	1.4186 (17)	C12—H12	0.9500
C1—C7	1.4734 (18)	C13—H13	0.9500
C2—C3	1.390 (2)	C14—C15	1.391 (2)
C3—C4	1.372 (2)	C14—C19	1.3950 (19)
C3—H3	0.9500	C15—C16	1.382 (2)
C4—C5	1.3917 (19)	C15—H15	0.9500
C4—H4	0.9500	C16—C17	1.387 (2)
C5—C6	1.3812 (19)	C16—H16	0.9500
C5—H5	0.9500	C17—C18	1.383 (2)
C6—H6	0.9500	C17—H17	0.9500
C7—C8	1.4966 (17)	C18—C19	1.3838 (19)
C8—C13	1.390 (2)	C18—H18	0.9500
C8—C9	1.3924 (19)	C19—H19	0.9500
C2—O1—H1O	101.7 (13)	C8—C9—H9	120.1
C7—N1—N2	120.53 (11)	C11—C10—C9	120.41 (13)
N1—N2—C14	117.92 (10)	C11—C10—H10	119.8
N1—N2—H2N	116.2 (11)	C9—C10—H10	119.8
C14—N2—H2N	119.7 (11)	C10—C11—C12	120.21 (13)
C6—C1—C2	117.62 (12)	C10—C11—H11	119.9
C6—C1—C7	120.35 (11)	C12—C11—H11	119.9
C2—C1—C7	122.03 (12)	C13—C12—C11	119.65 (14)
O1—C2—C3	118.34 (12)	C13—C12—H12	120.2
O1—C2—C1	121.80 (12)	C11—C12—H12	120.2
C3—C2—C1	119.86 (13)	C12—C13—C8	120.53 (13)
C4—C3—C2	120.79 (12)	C12—C13—H13	119.7
C4—C3—H3	119.6	C8—C13—H13	119.7
C2—C3—H3	119.6	C15—C14—N2	119.55 (12)
C3—C4—C5	120.54 (13)	C15—C14—C19	119.18 (12)
C3—C4—H4	119.7	N2—C14—C19	121.27 (12)
C5—C4—H4	119.7	C16—C15—C14	120.26 (13)
C6—C5—C4	118.98 (13)	C16—C15—H15	119.9
C6—C5—H5	120.5	C14—C15—H15	119.9
C4—C5—H5	120.5	C15—C16—C17	120.74 (14)
C5—C6—C1	122.19 (12)	C15—C16—H16	119.6
C5—C6—H6	118.9	C17—C16—H16	119.6
C1—C6—H6	118.9	C18—C17—C16	118.93 (13)
N1—C7—C1	117.18 (11)	C18—C17—H17	120.5
N1—C7—C8	123.63 (12)	C16—C17—H17	120.5
C1—C7—C8	119.19 (11)	C19—C18—C17	121.03 (13)
C13—C8—C9	119.42 (12)	C19—C18—H18	119.5
C13—C8—C7	120.76 (12)	C17—C18—H18	119.5
C9—C8—C7	119.79 (12)	C18—C19—C14	119.87 (13)
C10—C9—C8	119.73 (14)	C18—C19—H19	120.1
C10—C9—H9	120.1	C14—C19—H19	120.1
C7—N1—N2—C14	−176.29 (12)	N1—C7—C8—C9	−72.19 (18)
C6—C1—C2—O1	−178.88 (12)	C1—C7—C8—C9	108.42 (15)
C7—C1—C2—O1	1.1 (2)	C13—C8—C9—C10	1.7 (2)
C6—C1—C2—C3	1.25 (19)	C7—C8—C9—C10	−176.44 (13)
C7—C1—C2—C3	−178.79 (12)	C8—C9—C10—C11	−1.6 (2)
O1—C2—C3—C4	178.47 (12)	C9—C10—C11—C12	−0.2 (2)
C1—C2—C3—C4	−1.7 (2)	C10—C11—C12—C13	1.8 (2)
C2—C3—C4—C5	1.0 (2)	C11—C12—C13—C8	−1.7 (2)
C3—C4—C5—C6	0.1 (2)	C9—C8—C13—C12	−0.1 (2)
C4—C5—C6—C1	−0.5 (2)	C7—C8—C13—C12	178.04 (12)
C2—C1—C6—C5	−0.2 (2)	N1—N2—C14—C15	161.37 (13)
C7—C1—C6—C5	179.83 (12)	N1—N2—C14—C19	−19.38 (19)
N2—N1—C7—C1	177.56 (11)	N2—C14—C15—C16	179.33 (14)
N2—N1—C7—C8	−1.8 (2)	C19—C14—C15—C16	0.1 (2)
C6—C1—C7—N1	171.04 (12)	C14—C15—C16—C17	0.3 (2)
C2—C1—C7—N1	−8.92 (19)	C15—C16—C17—C18	−0.1 (2)
C6—C1—C7—C8	−9.52 (19)	C16—C17—C18—C19	−0.4 (2)
C2—C1—C7—C8	170.52 (12)	C17—C18—C19—C14	0.7 (2)
N1—C7—C8—C13	109.69 (16)	C15—C14—C19—C18	−0.5 (2)
C1—C7—C8—C13	−69.71 (17)	N2—C14—C19—C18	−179.78 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N1	0.85 (1)	1.76 (1)	2.5678 (14)	157 (2)
N2—H2N···O1i	0.89 (2)	2.43 (2)	3.2517 (16)	155 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N1	0.85 (1)	1.76 (1)	2.5678 (14)	157 (2)
N2—H2N⋯O1i	0.89 (2)	2.43 (2)	3.2517 (16)	155 (1)

Symmetry code: (i) .