(E)-N'-(2-Hydroxy-benzyl-idene)-2-(4-isobutyl-phen-yl)propanohydrazide.

The title hydrazide compound, C(20)H(24)N(2)O(2), exists in a trans configuration with respect to the acyclic C=N bond and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring motif. The mean plane through the formohydrazide unit is essentially planar [maximum deviation = 0.025 (2) Å], and forms dihedral angles of 24.45 (16) and 87.14 (16)° with the two benzene rings. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link neighbouring mol-ecules into extended chains along the c axis, which incorporate R(2) (2)(16) ring motifs. An inter-molecular C-H⋯π inter-action is also observed.

Related literature

For the metal coordination and pharmacological activity of the title compound, see: Bedia et al. (2006 ▶); Rodrìguez-Argüelles et al. (2004 ▶); Rollas et al. (2002 ▶); Terzioglu & Gürsoy (2003 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C20H24N2O2

M = 324.41

Monoclinic,

a = 5.5017 (2) Å

b = 33.0204 (14) Å

c = 9.7279 (4) Å

β = 91.731 (3)°

V = 1766.45 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.39 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.970, T max = 0.985

18817 measured reflections

4059 independent reflections

3190 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.181

S = 1.18

4059 reflections

228 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.28 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 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809050971/hb5254sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050971/hb5254Isup2.hkl

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

C20H24N2O2	F(000) = 696
Mr = 324.41	Dx = 1.220 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7778 reflections
a = 5.5017 (2) Å	θ = 2.4–30.0°
b = 33.0204 (14) Å	µ = 0.08 mm−1
c = 9.7279 (4) Å	T = 100 K
β = 91.731 (3)°	Block, colourless
V = 1766.45 (12) Å3	0.39 × 0.24 × 0.19 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4059 independent reflections
Radiation source: fine-focus sealed tube	3190 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
Tmin = 0.970, Tmax = 0.985	k = −38→42
18817 measured reflections	l = −12→12

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.0443P)2 + 2.5698P] where P = (Fo2 + 2Fc2)/3
4059 reflections	(Δ/σ)max < 0.001
228 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.28 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	−0.2604 (4)	0.18426 (6)	0.5584 (2)	0.0358 (5)
O2	0.3223 (3)	0.25847 (5)	0.60286 (15)	0.0209 (4)
N1	0.1237 (4)	0.20555 (6)	0.4218 (2)	0.0199 (5)
N2	0.3012 (4)	0.23282 (6)	0.3875 (2)	0.0210 (5)
C1	−0.1353 (6)	0.11240 (9)	0.2812 (3)	0.0364 (7)
H1A	−0.0286	0.1087	0.2099	0.044*
C2	−0.3138 (6)	0.08401 (9)	0.3013 (3)	0.0367 (8)
H2A	−0.3268	0.0614	0.2448	0.044*
C3	−0.4735 (6)	0.08962 (9)	0.4065 (4)	0.0385 (8)
H3A	−0.5952	0.0706	0.4205	0.046*
C4	−0.4540 (5)	0.12339 (9)	0.4918 (4)	0.0382 (7)
H4A	−0.5625	0.1268	0.5624	0.046*
C5	−0.2736 (5)	0.15194 (8)	0.4721 (3)	0.0285 (6)
C6	−0.1095 (5)	0.14680 (8)	0.3650 (3)	0.0269 (6)
C7	0.0819 (5)	0.17603 (8)	0.3390 (3)	0.0276 (6)
H7A	0.1748	0.1732	0.2613	0.033*
C8	0.3850 (4)	0.25968 (7)	0.4827 (2)	0.0156 (5)
C9	0.5550 (5)	0.29208 (8)	0.4303 (3)	0.0235 (5)
H9A	0.6170	0.2834	0.3417	0.028*
C10	0.4016 (5)	0.33029 (8)	0.4081 (3)	0.0235 (5)
C11	0.4132 (5)	0.36299 (8)	0.4983 (3)	0.0310 (6)
H11A	0.5260	0.3628	0.5715	0.037*
C12	0.2587 (5)	0.39598 (8)	0.4807 (3)	0.0277 (6)
H12A	0.2735	0.4177	0.5411	0.033*
C13	0.0842 (6)	0.39741 (8)	0.3763 (3)	0.0277 (6)
C14	0.0756 (8)	0.36506 (9)	0.2855 (3)	0.0518 (11)
H14A	−0.0389	0.3652	0.2131	0.062*
C15	0.2335 (7)	0.33241 (9)	0.2998 (3)	0.0438 (9)
H15A	0.2259	0.3116	0.2354	0.053*
C16	−0.0929 (6)	0.43214 (8)	0.3616 (3)	0.0319 (7)
H16A	−0.1484	0.4392	0.4522	0.038*
H16B	−0.2334	0.4230	0.3075	0.038*
C17	0.0063 (6)	0.47049 (8)	0.2944 (3)	0.0331 (7)
H17A	0.1393	0.4809	0.3537	0.040*
C18	−0.1918 (7)	0.50278 (9)	0.2851 (3)	0.0435 (8)
H18A	−0.1264	0.5272	0.2472	0.065*
H18B	−0.2499	0.5082	0.3754	0.065*
H18C	−0.3239	0.4933	0.2270	0.065*
C19	0.1076 (7)	0.46188 (9)	0.1530 (3)	0.0402 (8)
H19A	0.1558	0.4869	0.1114	0.060*
H19B	−0.0152	0.4491	0.0960	0.060*
H19C	0.2460	0.4443	0.1628	0.060*
C20	0.7674 (5)	0.29712 (9)	0.5318 (4)	0.0423 (8)
H20A	0.8636	0.2729	0.5335	0.063*
H20B	0.7074	0.3022	0.6218	0.063*
H20C	0.8658	0.3195	0.5043	0.063*
H1N2	0.346 (6)	0.2342 (9)	0.303 (3)	0.034 (9)*
H1O1	−0.127 (8)	0.1984 (12)	0.539 (4)	0.064 (13)*

	U11	U22	U33	U12	U13	U23
O1	0.0260 (11)	0.0248 (10)	0.0569 (14)	−0.0014 (8)	0.0068 (10)	−0.0075 (9)
O2	0.0300 (10)	0.0253 (9)	0.0074 (7)	0.0012 (7)	0.0012 (7)	−0.0001 (7)
N1	0.0248 (11)	0.0194 (10)	0.0150 (9)	−0.0027 (8)	−0.0055 (8)	0.0027 (8)
N2	0.0329 (12)	0.0221 (11)	0.0083 (9)	−0.0060 (9)	0.0021 (8)	0.0006 (8)
C1	0.060 (2)	0.0304 (15)	0.0184 (13)	−0.0137 (14)	−0.0084 (13)	0.0022 (11)
C2	0.057 (2)	0.0258 (15)	0.0268 (14)	−0.0115 (13)	−0.0136 (14)	0.0030 (12)
C3	0.0319 (16)	0.0256 (15)	0.057 (2)	−0.0059 (12)	−0.0153 (15)	0.0061 (14)
C4	0.0206 (14)	0.0292 (15)	0.065 (2)	0.0004 (11)	−0.0005 (14)	−0.0014 (14)
C5	0.0243 (13)	0.0198 (13)	0.0409 (16)	0.0032 (10)	−0.0087 (12)	0.0015 (11)
C6	0.0379 (15)	0.0226 (13)	0.0192 (12)	−0.0055 (11)	−0.0128 (11)	0.0059 (10)
C7	0.0434 (16)	0.0256 (14)	0.0134 (11)	−0.0049 (12)	−0.0048 (11)	0.0025 (10)
C8	0.0146 (11)	0.0190 (11)	0.0132 (10)	0.0031 (9)	−0.0001 (8)	0.0004 (9)
C9	0.0239 (13)	0.0202 (12)	0.0272 (13)	−0.0009 (10)	0.0118 (10)	−0.0033 (10)
C10	0.0311 (14)	0.0191 (12)	0.0212 (12)	−0.0024 (10)	0.0130 (10)	0.0016 (10)
C11	0.0232 (14)	0.0261 (14)	0.0435 (16)	−0.0025 (11)	−0.0013 (12)	−0.0117 (12)
C12	0.0255 (14)	0.0239 (13)	0.0339 (15)	−0.0010 (11)	0.0057 (11)	−0.0101 (11)
C13	0.0454 (17)	0.0201 (13)	0.0181 (12)	0.0021 (11)	0.0076 (11)	0.0042 (10)
C14	0.105 (3)	0.0295 (16)	0.0196 (14)	0.0204 (18)	−0.0219 (17)	−0.0017 (12)
C15	0.095 (3)	0.0228 (14)	0.0131 (12)	0.0159 (16)	−0.0038 (15)	−0.0027 (11)
C16	0.0447 (18)	0.0244 (14)	0.0265 (14)	0.0061 (12)	0.0002 (12)	0.0016 (11)
C17	0.0498 (19)	0.0229 (14)	0.0262 (14)	0.0030 (12)	−0.0069 (13)	0.0019 (11)
C18	0.062 (2)	0.0271 (15)	0.0413 (18)	0.0081 (15)	−0.0068 (16)	0.0036 (13)
C19	0.057 (2)	0.0328 (16)	0.0305 (16)	0.0008 (14)	−0.0011 (14)	0.0074 (13)
C20	0.0220 (14)	0.0266 (15)	0.078 (2)	−0.0012 (11)	−0.0006 (15)	−0.0134 (15)

O1—C5	1.359 (3)	C11—C12	1.389 (4)
O1—H1O1	0.89 (4)	C11—H11A	0.9300
O2—C8	1.229 (3)	C12—C13	1.377 (4)
N1—C7	1.281 (3)	C12—H12A	0.9300
N1—N2	1.377 (3)	C13—C14	1.386 (4)
N2—C8	1.354 (3)	C13—C16	1.509 (4)
N2—H1N2	0.86 (3)	C14—C15	1.389 (4)
C1—C2	1.376 (4)	C14—H14A	0.9300
C1—C6	1.403 (4)	C15—H15A	0.9300
C1—H1A	0.9300	C16—C17	1.533 (4)
C2—C3	1.382 (5)	C16—H16A	0.9700
C2—H2A	0.9300	C16—H16B	0.9700
C3—C4	1.392 (4)	C17—C18	1.526 (4)
C3—H3A	0.9300	C17—C19	1.526 (4)
C4—C5	1.387 (4)	C17—H17A	0.9800
C4—H4A	0.9300	C18—H18A	0.9600
C5—C6	1.409 (4)	C18—H18B	0.9600
C6—C7	1.456 (4)	C18—H18C	0.9600
C7—H7A	0.9300	C19—H19A	0.9600
C8—C9	1.519 (3)	C19—H19B	0.9600
C9—C20	1.516 (4)	C19—H19C	0.9600
C9—C10	1.530 (4)	C20—H20A	0.9600
C9—H9A	0.9800	C20—H20B	0.9600
C10—C15	1.382 (4)	C20—H20C	0.9600
C10—C11	1.392 (4)
C5—O1—H1O1	108 (3)	C13—C12—H12A	119.1
C7—N1—N2	117.4 (2)	C11—C12—H12A	119.1
C8—N2—N1	119.4 (2)	C12—C13—C14	117.0 (3)
C8—N2—H1N2	121 (2)	C12—C13—C16	122.0 (2)
N1—N2—H1N2	119 (2)	C14—C13—C16	121.0 (3)
C2—C1—C6	122.0 (3)	C13—C14—C15	121.6 (3)
C2—C1—H1A	119.0	C13—C14—H14A	119.2
C6—C1—H1A	119.0	C15—C14—H14A	119.2
C1—C2—C3	119.1 (3)	C10—C15—C14	121.2 (3)
C1—C2—H2A	120.4	C10—C15—H15A	119.4
C3—C2—H2A	120.4	C14—C15—H15A	119.4
C2—C3—C4	120.6 (3)	C13—C16—C17	115.5 (3)
C2—C3—H3A	119.7	C13—C16—H16A	108.4
C4—C3—H3A	119.7	C17—C16—H16A	108.4
C5—C4—C3	120.3 (3)	C13—C16—H16B	108.4
C5—C4—H4A	119.8	C17—C16—H16B	108.4
C3—C4—H4A	119.8	H16A—C16—H16B	107.5
O1—C5—C4	118.3 (3)	C18—C17—C19	110.9 (2)
O1—C5—C6	121.9 (2)	C18—C17—C16	109.8 (3)
C4—C5—C6	119.8 (3)	C19—C17—C16	112.0 (2)
C1—C6—C5	118.1 (3)	C18—C17—H17A	108.0
C1—C6—C7	119.8 (3)	C19—C17—H17A	108.0
C5—C6—C7	122.1 (2)	C16—C17—H17A	108.0
N1—C7—C6	120.8 (3)	C17—C18—H18A	109.5
N1—C7—H7A	119.6	C17—C18—H18B	109.5
C6—C7—H7A	119.6	H18A—C18—H18B	109.5
O2—C8—N2	122.0 (2)	C17—C18—H18C	109.5
O2—C8—C9	122.4 (2)	H18A—C18—H18C	109.5
N2—C8—C9	115.6 (2)	H18B—C18—H18C	109.5
C20—C9—C8	109.2 (2)	C17—C19—H19A	109.5
C20—C9—C10	114.4 (2)	C17—C19—H19B	109.5
C8—C9—C10	106.6 (2)	H19A—C19—H19B	109.5
C20—C9—H9A	108.8	C17—C19—H19C	109.5
C8—C9—H9A	108.8	H19A—C19—H19C	109.5
C10—C9—H9A	108.8	H19B—C19—H19C	109.5
C15—C10—C11	117.3 (3)	C9—C20—H20A	109.5
C15—C10—C9	120.2 (2)	C9—C20—H20B	109.5
C11—C10—C9	122.4 (2)	H20A—C20—H20B	109.5
C12—C11—C10	120.9 (3)	C9—C20—H20C	109.5
C12—C11—H11A	119.5	H20A—C20—H20C	109.5
C10—C11—H11A	119.5	H20B—C20—H20C	109.5
C13—C12—C11	121.9 (3)
C7—N1—N2—C8	−167.2 (2)	N2—C8—C9—C10	99.7 (2)
C6—C1—C2—C3	0.4 (4)	C20—C9—C10—C15	167.3 (3)
C1—C2—C3—C4	−0.3 (4)	C8—C9—C10—C15	−71.9 (3)
C2—C3—C4—C5	0.0 (4)	C20—C9—C10—C11	−16.6 (4)
C3—C4—C5—O1	−179.5 (3)	C8—C9—C10—C11	104.2 (3)
C3—C4—C5—C6	0.1 (4)	C15—C10—C11—C12	1.0 (4)
C2—C1—C6—C5	−0.2 (4)	C9—C10—C11—C12	−175.2 (3)
C2—C1—C6—C7	−179.7 (3)	C10—C11—C12—C13	1.7 (4)
O1—C5—C6—C1	179.6 (2)	C11—C12—C13—C14	−2.5 (5)
C4—C5—C6—C1	0.0 (4)	C11—C12—C13—C16	176.6 (3)
O1—C5—C6—C7	−0.9 (4)	C12—C13—C14—C15	0.7 (5)
C4—C5—C6—C7	179.4 (3)	C16—C13—C14—C15	−178.4 (3)
N2—N1—C7—C6	−177.5 (2)	C11—C10—C15—C14	−2.8 (5)
C1—C6—C7—N1	−173.3 (2)	C9—C10—C15—C14	173.5 (3)
C5—C6—C7—N1	7.3 (4)	C13—C14—C15—C10	2.0 (6)
N1—N2—C8—O2	6.1 (3)	C12—C13—C16—C17	79.8 (3)
N1—N2—C8—C9	−172.1 (2)	C14—C13—C16—C17	−101.1 (3)
O2—C8—C9—C20	45.5 (3)	C13—C16—C17—C18	179.5 (2)
N2—C8—C9—C20	−136.3 (2)	C13—C16—C17—C19	55.8 (3)
O2—C8—C9—C10	−78.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.87 (3)	1.96 (3)	2.790 (2)	159 (3)
O1—H1O1···N1	0.90 (4)	1.83 (4)	2.626 (3)	147 (4)
C14—H14A···O1i	0.93	2.51	3.272 (4)	139
C20—H20C···Cg1ii	0.96	2.80	3.722 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.87 (3)	1.96 (3)	2.790 (2)	159 (3)
O1—H1O1⋯N1	0.90 (4)	1.83 (4)	2.626 (3)	147 (4)
C14—H14A⋯O1i	0.93	2.51	3.272 (4)	139
C20—H20C⋯Cg1ii	0.96	2.80	3.722 (3)	161

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the C10–C15 benzene ring.