N'-[(1E)-4-Diethyl-amino-2-hy-droxy-benz-idene]benzohydrazide.

In the title compound, C(18)H(21)N(3)O(2), the dihedral angle between the phenyl and benzene rings is 36.85 (10)°. The methyl C atom of one of the ethyl groups is disordered over two positions with site occupancies of 0.810 (8) and 0.190 (8). The mol-ecular structure is stabilized by a classical intra-molecular O-H⋯N hydrogen bond. The crystal structure exhibits weak inter-molecular N-H⋯O, C-H⋯O and C-H⋯π inter-actions.

Related literature

For the biological activity of Schiff base ligands, see: Kelley et al. (1995 ▶); Pandeya et al. (1999 ▶); Singh & Dash (1988 ▶); Tarafder et al. (2002 ▶). For related strucutures, see: Bahron et al. (2010 ▶); Manvizhi et al. (2010 ▶).

Experimental

Crystal data

C18H21N3O2

M = 311.38

Monoclinic,

a = 10.591 (5) Å

b = 16.733 (6) Å

c = 9.671 (5) Å

β = 102.316 (5)°

V = 1674.4 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 295 K

0.28 × 0.24 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.977, T max = 0.984

9666 measured reflections

3884 independent reflections

2466 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.072

wR(F 2) = 0.203

S = 1.05

3884 reflections

222 parameters

6 restraints

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681103652X/rk2298sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103652X/rk2298Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103652X/rk2298Isup3.cml

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

C18H21N3O2	F(000) = 664
Mr = 311.38	Dx = 1.235 Mg m−3
Monoclinic, P21/c	Melting point: 500 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.591 (5) Å	Cell parameters from 4483 reflections
b = 16.733 (6) Å	θ = 2.9–29.1°
c = 9.671 (5) Å	µ = 0.08 mm−1
β = 102.316 (5)°	T = 295 K
V = 1674.4 (13) Å3	Block, pale yellow
Z = 4	0.28 × 0.24 × 0.20 mm

Oxford Diffraction Xcalibur Eos diffractometer	3884 independent reflections
Radiation source: fine–focus sealed tube	2466 reflections with I > 2σ(I)
graphite	Rint = 0.031
φ– and ω–scans	θmax = 29.2°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	h = −14→13
Tmin = 0.977, Tmax = 0.984	k = −22→18
9666 measured reflections	l = −12→13

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)] = 0.072	H-atom parameters constrained
wR(F2) = 0.203	w = 1/[σ2(Fo2) + (0.0782P)2 + 0.8512P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
3884 reflections	Δρmax = 0.43 e Å−3
222 parameters	Δρmin = −0.40 e Å−3
6 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.022 (3)

Geometry. All s.u.'s (except the e.s.d. 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	Occ. (<1)
C1	0.3790 (2)	0.27667 (16)	0.7824 (2)	0.0476 (6)
C2	0.2753 (3)	0.2435 (2)	0.8285 (3)	0.0669 (8)
H2	0.2877	0.1980	0.8850	0.080*
C3	0.1545 (3)	0.2771 (3)	0.7914 (5)	0.0950 (13)
H3	0.0849	0.2538	0.8207	0.114*
C4	0.1374 (4)	0.3448 (4)	0.7114 (4)	0.1128 (17)
H4	0.0554	0.3672	0.6850	0.135*
C5	0.2401 (5)	0.3807 (3)	0.6692 (4)	0.1231 (19)
H5	0.2282	0.4282	0.6182	0.148*
C6	0.3614 (3)	0.3455 (2)	0.7031 (3)	0.0831 (11)
H6	0.4305	0.3684	0.6722	0.100*
C7	0.5058 (2)	0.23618 (14)	0.8256 (2)	0.0416 (5)
C8	0.7610 (2)	0.19544 (16)	0.6584 (2)	0.0477 (6)
H8	0.7314	0.2260	0.5776	0.057*
C9	0.8774 (2)	0.14947 (15)	0.6699 (2)	0.0436 (6)
C10	0.9440 (2)	0.15018 (17)	0.5596 (2)	0.0510 (6)
H10	0.9133	0.1823	0.4812	0.061*
C11	1.0526 (2)	0.10543 (18)	0.5627 (3)	0.0559 (7)
H11	1.0945	0.1082	0.4875	0.067*
C12	1.1017 (2)	0.05524 (17)	0.6782 (3)	0.0524 (6)
C13	1.0364 (2)	0.05409 (16)	0.7911 (3)	0.0512 (6)
H13	1.0676	0.0222	0.8697	0.061*
C14	0.9275 (2)	0.09940 (15)	0.7862 (2)	0.0449 (6)
C15	1.2777 (3)	0.0098 (2)	0.5648 (3)	0.0690 (8)
H15A	1.2157	0.0150	0.4757	0.083*
H15B	1.3226	−0.0406	0.5630	0.083*
C16	1.3733 (3)	0.0763 (2)	0.5773 (4)	0.0863 (10)
H16A	1.3298	0.1264	0.5793	0.129*
H16B	1.4140	0.0751	0.4976	0.129*
H16C	1.4377	0.0700	0.6630	0.129*
C17	1.2575 (4)	−0.0495 (4)	0.7989 (4)	0.1165 (17)
H17A	1.1854	−0.0671	0.8385	0.140*	0.810 (8)
H17B	1.2922	−0.0961	0.7605	0.140*	0.810 (8)
H17C	1.3506	−0.0446	0.8124	0.140*	0.190 (8)
H17D	1.2359	−0.0233	0.8803	0.140*	0.190 (8)
N1	0.58174 (18)	0.23775 (13)	0.73010 (19)	0.0478 (5)
H1	0.5590	0.2647	0.6531	0.057*
N2	0.69687 (17)	0.19532 (13)	0.7574 (2)	0.0473 (5)
N3	1.2080 (2)	0.00784 (18)	0.6801 (3)	0.0766 (8)
O1	0.53870 (16)	0.20183 (12)	0.93992 (16)	0.0574 (5)
O2	0.86897 (17)	0.09411 (12)	0.89825 (18)	0.0628 (6)
H2A	0.8054	0.1234	0.8849	0.094*
C18	1.3519 (5)	−0.0184 (4)	0.9069 (6)	0.121 (2)	0.810 (8)
H18A	1.3185	0.0276	0.9465	0.182*	0.810 (8)
H18B	1.4256	−0.0031	0.8699	0.182*	0.810 (8)
H18C	1.3772	−0.0581	0.9791	0.182*	0.810 (8)
C18A	1.241 (2)	−0.1276 (11)	0.827 (2)	0.122 (7)	0.190 (8)
H18D	1.2950	−0.1413	0.9165	0.183*	0.190 (8)
H18E	1.2651	−0.1598	0.7539	0.183*	0.190 (8)
H18F	1.1524	−0.1373	0.8287	0.183*	0.190 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0438 (13)	0.0650 (16)	0.0350 (10)	0.0059 (11)	0.0108 (9)	−0.0109 (11)
C2	0.0472 (15)	0.072 (2)	0.085 (2)	−0.0064 (14)	0.0217 (14)	−0.0232 (16)
C3	0.0463 (17)	0.121 (3)	0.119 (3)	−0.001 (2)	0.0213 (19)	−0.053 (3)
C4	0.071 (2)	0.185 (5)	0.080 (2)	0.063 (3)	0.0093 (19)	−0.023 (3)
C5	0.127 (3)	0.170 (4)	0.083 (2)	0.097 (3)	0.047 (2)	0.046 (3)
C6	0.086 (2)	0.106 (3)	0.0680 (18)	0.044 (2)	0.0400 (17)	0.0290 (18)
C7	0.0392 (11)	0.0510 (14)	0.0347 (10)	−0.0056 (10)	0.0080 (9)	−0.0076 (10)
C8	0.0398 (12)	0.0637 (16)	0.0396 (11)	0.0020 (11)	0.0084 (9)	0.0022 (11)
C9	0.0342 (11)	0.0578 (15)	0.0393 (11)	−0.0021 (10)	0.0088 (9)	0.0000 (10)
C10	0.0419 (12)	0.0728 (18)	0.0390 (11)	0.0034 (12)	0.0102 (10)	0.0084 (11)
C11	0.0470 (14)	0.0810 (19)	0.0441 (13)	0.0054 (13)	0.0199 (10)	0.0039 (12)
C12	0.0401 (13)	0.0704 (18)	0.0479 (13)	0.0053 (12)	0.0122 (10)	0.0003 (12)
C13	0.0427 (12)	0.0659 (17)	0.0462 (12)	0.0059 (12)	0.0122 (10)	0.0089 (12)
C14	0.0386 (12)	0.0583 (15)	0.0398 (11)	−0.0051 (11)	0.0129 (9)	0.0006 (10)
C15	0.0591 (16)	0.081 (2)	0.0721 (18)	0.0123 (16)	0.0255 (14)	−0.0058 (16)
C16	0.079 (2)	0.093 (3)	0.089 (2)	−0.003 (2)	0.0219 (18)	0.006 (2)
C17	0.080 (2)	0.200 (5)	0.078 (2)	0.077 (3)	0.0359 (17)	0.044 (2)
N1	0.0394 (10)	0.0662 (14)	0.0391 (9)	0.0089 (9)	0.0115 (8)	0.0044 (9)
N2	0.0364 (10)	0.0636 (14)	0.0422 (10)	0.0034 (9)	0.0094 (8)	−0.0003 (9)
N3	0.0568 (14)	0.110 (2)	0.0699 (15)	0.0288 (14)	0.0290 (12)	0.0117 (13)
O1	0.0563 (10)	0.0785 (13)	0.0387 (9)	0.0050 (9)	0.0128 (7)	0.0050 (8)
O2	0.0574 (11)	0.0875 (14)	0.0505 (10)	0.0146 (10)	0.0272 (8)	0.0179 (9)
C18	0.108 (4)	0.140 (5)	0.121 (4)	0.037 (3)	0.036 (2)	0.043 (3)
C18A	0.110 (17)	0.195 (10)	0.058 (11)	0.065 (16)	0.010 (10)	0.029 (14)

C1—C6	1.374 (4)	C14—O2	1.362 (3)
C1—C2	1.387 (4)	C15—N3	1.464 (3)
C1—C7	1.483 (3)	C15—C16	1.492 (5)
C2—C3	1.373 (5)	C15—H15A	0.9700
C2—H2	0.9300	C15—H15B	0.9700
C3—C4	1.363 (6)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.378 (7)	C16—H16C	0.9600
C4—H4	0.9300	C17—C18A	1.353 (16)
C5—C6	1.387 (5)	C17—C18	1.384 (7)
C5—H5	0.9300	C17—N3	1.502 (5)
C6—H6	0.9300	C17—H17A	0.9700
C7—O1	1.229 (3)	C17—H17B	0.9700
C7—N1	1.348 (3)	C17—H17C	0.9700
C8—N2	1.287 (3)	C17—H17D	0.9700
C8—C9	1.437 (3)	N1—N2	1.387 (3)
C8—H8	0.9300	N1—H1	0.8600
C9—C10	1.399 (3)	O2—H2A	0.8200
C9—C14	1.412 (3)	C18—H17C	1.0114
C10—C11	1.367 (3)	C18—H17D	1.2036
C10—H10	0.9300	C18—H18A	0.9600
C11—C12	1.406 (4)	C18—H18B	0.9600
C11—H11	0.9300	C18—H18C	0.9600
C12—N3	1.374 (3)	C18A—H18D	0.9600
C12—C13	1.411 (3)	C18A—H18E	0.9600
C13—C14	1.372 (3)	C18A—H18F	0.9600
C13—H13	0.9300
C6—C1—C2	119.5 (3)	H16A—C16—H16B	109.5
C6—C1—C7	123.2 (2)	C15—C16—H16C	109.5
C2—C1—C7	117.3 (2)	H16A—C16—H16C	109.5
C3—C2—C1	120.7 (4)	H16B—C16—H16C	109.5
C3—C2—H2	119.7	C18A—C17—C18	108.4 (9)
C1—C2—H2	119.7	C18A—C17—N3	136.9 (10)
C4—C3—C2	119.5 (4)	C18—C17—N3	114.5 (5)
C4—C3—H3	120.3	C18A—C17—H17A	59.0
C2—C3—H3	120.3	C18—C17—H17A	108.6
C3—C4—C5	120.9 (3)	N3—C17—H17A	108.6
C3—C4—H4	119.6	C18A—C17—H17B	51.1
C5—C4—H4	119.6	C18—C17—H17B	108.6
C4—C5—C6	119.6 (4)	N3—C17—H17B	108.6
C4—C5—H5	120.2	H17A—C17—H17B	107.6
C6—C5—H5	120.2	C18A—C17—H17C	102.8
C1—C6—C5	119.8 (3)	C18—C17—H17C	46.9
C1—C6—H6	120.1	N3—C17—H17C	103.2
C5—C6—H6	120.1	H17A—C17—H17C	146.7
O1—C7—N1	122.0 (2)	H17B—C17—H17C	70.2
O1—C7—C1	122.2 (2)	C18A—C17—H17D	102.4
N1—C7—C1	115.8 (2)	C18—C17—H17D	58.4
N2—C8—C9	121.5 (2)	N3—C17—H17D	103.2
N2—C8—H8	119.3	H17A—C17—H17D	58.3
C9—C8—H8	119.3	H17B—C17—H17D	148.1
C10—C9—C14	116.5 (2)	H17C—C17—H17D	105.2
C10—C9—C8	120.0 (2)	C7—N1—N2	119.22 (19)
C14—C9—C8	123.4 (2)	C7—N1—H1	120.4
C11—C10—C9	122.5 (2)	N2—N1—H1	120.4
C11—C10—H10	118.7	C8—N2—N1	116.09 (19)
C9—C10—H10	118.7	C12—N3—C15	121.5 (2)
C10—C11—C12	120.7 (2)	C12—N3—C17	122.0 (2)
C10—C11—H11	119.6	C15—N3—C17	116.5 (2)
C12—C11—H11	119.6	C14—O2—H2A	109.5
N3—C12—C11	121.2 (2)	H17C—C18—H17D	87.7
N3—C12—C13	121.1 (2)	C17—C18—H18A	109.5
C11—C12—C13	117.6 (2)	H17C—C18—H18A	140.6
C14—C13—C12	120.8 (2)	H17D—C18—H18A	72.1
C14—C13—H13	119.6	C17—C18—H18B	109.5
C12—C13—H13	119.6	H17C—C18—H18B	68.6
O2—C14—C13	117.3 (2)	H17D—C18—H18B	144.4
O2—C14—C9	121.0 (2)	C17—C18—H18C	109.5
C13—C14—C9	121.7 (2)	H17C—C18—H18C	107.8
N3—C15—C16	113.5 (3)	H17D—C18—H18C	102.8
N3—C15—H15A	108.9	C17—C18A—H18D	109.5
C16—C15—H15A	108.9	C17—C18A—H18E	109.5
N3—C15—H15B	108.9	H18D—C18A—H18E	109.5
C16—C15—H15B	108.9	C17—C18A—H18F	109.5
H15A—C15—H15B	107.7	H18D—C18A—H18F	109.5
C15—C16—H16A	109.5	H18E—C18A—H18F	109.5
C15—C16—H16B	109.5
C6—C1—C2—C3	2.3 (4)	C12—C13—C14—O2	179.0 (2)
C7—C1—C2—C3	−179.3 (3)	C12—C13—C14—C9	−0.8 (4)
C1—C2—C3—C4	−1.6 (5)	C10—C9—C14—O2	−179.5 (2)
C2—C3—C4—C5	−1.0 (6)	C8—C9—C14—O2	−2.3 (4)
C3—C4—C5—C6	2.9 (7)	C10—C9—C14—C13	0.3 (4)
C2—C1—C6—C5	−0.4 (5)	C8—C9—C14—C13	177.5 (2)
C7—C1—C6—C5	−178.7 (3)	O1—C7—N1—N2	4.1 (3)
C4—C5—C6—C1	−2.1 (6)	C1—C7—N1—N2	−174.4 (2)
C6—C1—C7—O1	145.2 (3)	C9—C8—N2—N1	−175.9 (2)
C2—C1—C7—O1	−33.2 (3)	C7—N1—N2—C8	176.0 (2)
C6—C1—C7—N1	−36.4 (3)	C11—C12—N3—C15	2.4 (4)
C2—C1—C7—N1	145.3 (2)	C13—C12—N3—C15	−178.8 (3)
N2—C8—C9—C10	179.3 (2)	C11—C12—N3—C17	−176.6 (4)
N2—C8—C9—C14	2.1 (4)	C13—C12—N3—C17	2.2 (5)
C14—C9—C10—C11	−0.3 (4)	C16—C15—N3—C12	82.8 (4)
C8—C9—C10—C11	−177.6 (3)	C16—C15—N3—C17	−98.1 (4)
C9—C10—C11—C12	0.8 (4)	C18A—C17—N3—C12	93.6 (15)
C10—C11—C12—N3	177.6 (3)	C18—C17—N3—C12	−92.3 (4)
C10—C11—C12—C13	−1.2 (4)	C18A—C17—N3—C15	−85.5 (15)
N3—C12—C13—C14	−177.6 (3)	C18—C17—N3—C15	88.6 (4)
C11—C12—C13—C14	1.2 (4)

Cg2 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N2	0.82	1.92	2.643 (3)	147
N1—H1···O1i	0.86	2.10	2.926 (3)	160
C8—H8···O1i	0.93	2.50	3.293 (3)	144
C3—H3···Cg2ii	0.93	2.97	3.468 (5)	115

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N2	0.82	1.92	2.643 (3)	147
N1—H1⋯O1i	0.86	2.10	2.926 (3)	160
C8—H8⋯O1i	0.93	2.50	3.293 (3)	144
C3—H3⋯Cg2ii	0.93	2.97	3.468 (5)	115

Symmetry codes: (i) ; (ii) .