N'-(4-Diethyl-amino-2-hy-droxy-benzyl-idene)-4-(dimethyl-amino)-benzo-hydrazide methanol monosolvate.

The title compound, C(20)H(26)N(4)O(2)·CH(3)OH, was prepared by the reaction of 4-diethyl-amino-2-hy-droxy-benzaldehyde with 4-(dimethyl-amino)-benzohydrazide. The dihedral angle between the two benzene rings is 13.6 (3)° and an intra-molecular O-H⋯N hydrogen bond generates an S(6) ring. In the crystal, the hydrazone and methanol mol-ecules are linked through inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming chains along a.

Related literature

For the biological properties of hydrazones, see: Ajani et al. (2010 ▶); Zhang et al. (2010 ▶); Angelusiu et al. (2010 ▶). For similar structures, see: Huang & Wu (2010 ▶); Khaledi et al. (2010 ▶); Zhou & Yang (2010 ▶); Ji & Lu (2010 ▶); Singh & Singh (2010 ▶); Ahmad et al. (2010 ▶). For hydrogen-bond motifs, see Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H26N4O2·CH4O

M = 386.49

Triclinic,

a = 6.786 (3) Å

b = 11.791 (3) Å

c = 14.252 (2) Å

α = 111.511 (3)°

β = 92.811 (2)°

γ = 96.492 (2)°

V = 1049.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.27 × 0.23 × 0.21 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.978, T max = 0.983

7543 measured reflections

4421 independent reflections

1809 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.189

S = 1.00

4421 reflections

263 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811019957/sj5154sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019957/sj5154Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019957/sj5154Isup3.cml

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

C20H26N4O2·CH4O	Z = 2
Mr = 386.49	F(000) = 416
Triclinic, P1	Dx = 1.224 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.786 (3) Å	Cell parameters from 765 reflections
b = 11.791 (3) Å	θ = 2.6–24.5°
c = 14.252 (2) Å	µ = 0.08 mm−1
α = 111.511 (3)°	T = 298 K
β = 92.811 (2)°	Block, colorless
γ = 96.492 (2)°	0.27 × 0.23 × 0.21 mm
V = 1049.1 (6) Å3

Bruker SMART CCD area-detector diffractometer	4421 independent reflections
Radiation source: fine-focus sealed tube	1809 reflections with I > 2σ(I)
graphite	Rint = 0.045
ω scans	θmax = 27.0°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
Tmin = 0.978, Tmax = 0.983	k = −15→15
7543 measured reflections	l = −15→18

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.189	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0676P)2] where P = (Fo2 + 2Fc2)/3
4421 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.30 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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	−0.1048 (3)	0.5092 (2)	0.2045 (2)	0.0741 (8)
H1	−0.0686	0.4564	0.2235	0.111*
O2	−0.0566 (3)	0.2247 (2)	0.3184 (2)	0.0770 (8)
O3	0.6751 (4)	0.3787 (2)	0.3427 (2)	0.0907 (9)
H3	0.7586	0.3321	0.3371	0.136*
N1	0.1680 (4)	0.3808 (2)	0.2520 (2)	0.0549 (7)
N2	0.2452 (4)	0.2985 (2)	0.2885 (2)	0.0564 (8)
N3	0.4202 (4)	−0.1790 (2)	0.3829 (2)	0.0632 (8)
N4	0.1131 (4)	0.7762 (2)	0.0366 (2)	0.0705 (9)
C1	0.2398 (4)	0.5230 (2)	0.1692 (2)	0.0488 (8)
C2	0.0478 (5)	0.5553 (3)	0.1644 (2)	0.0487 (8)
C3	0.0066 (4)	0.6387 (3)	0.1211 (2)	0.0535 (9)
H3A	−0.1218	0.6588	0.1194	0.064*
C4	0.1541 (5)	0.6933 (3)	0.0801 (2)	0.0525 (8)
C5	0.3450 (5)	0.6589 (3)	0.0828 (3)	0.0649 (10)
H5	0.4457	0.6922	0.0546	0.078*
C6	0.3848 (5)	0.5769 (3)	0.1263 (3)	0.0594 (9)
H6	0.5130	0.5564	0.1273	0.071*
C7	0.2927 (5)	0.4383 (3)	0.2145 (2)	0.0523 (8)
H7	0.4248	0.4246	0.2168	0.063*
C8	0.1245 (5)	0.2195 (3)	0.3155 (2)	0.0522 (8)
C9	0.2154 (4)	0.1219 (3)	0.3371 (2)	0.0470 (8)
C10	0.0978 (5)	0.0474 (3)	0.3749 (3)	0.0573 (9)
H10	−0.0301	0.0644	0.3897	0.069*
C11	0.1637 (5)	−0.0504 (3)	0.3910 (2)	0.0596 (9)
H11	0.0806	−0.0973	0.4173	0.071*
C12	0.3538 (5)	−0.0806 (3)	0.3687 (2)	0.0505 (8)
C13	0.4723 (4)	−0.0056 (3)	0.3301 (2)	0.0575 (9)
H13	0.6001	−0.0224	0.3148	0.069*
C14	0.4036 (5)	0.0927 (3)	0.3145 (2)	0.0553 (9)
H14	0.4855	0.1402	0.2883	0.066*
C15	0.2976 (6)	−0.2536 (3)	0.4256 (3)	0.0780 (11)
H15A	0.2808	−0.2051	0.4946	0.117*
H15B	0.3614	−0.3231	0.4233	0.117*
H15C	0.1696	−0.2821	0.3869	0.117*
C16	0.6191 (5)	−0.2071 (3)	0.3638 (3)	0.0789 (12)
H16A	0.6412	−0.2160	0.2956	0.118*
H16B	0.6347	−0.2824	0.3728	0.118*
H16C	0.7139	−0.1414	0.4103	0.118*
C17	0.2791 (6)	0.8609 (3)	0.0203 (3)	0.0792 (12)
H17A	0.2346	0.9396	0.0307	0.095*
H17B	0.3917	0.8751	0.0698	0.095*
C18	0.3427 (6)	0.8094 (4)	−0.0821 (3)	0.1027 (14)
H18A	0.3853	0.7310	−0.0929	0.154*
H18B	0.4511	0.8645	−0.0893	0.154*
H18C	0.2332	0.7989	−0.1312	0.154*
C19	−0.0856 (5)	0.8062 (3)	0.0254 (3)	0.0603 (9)
H19A	−0.1818	0.7332	0.0115	0.072*
H19B	−0.0975	0.8310	−0.0322	0.072*
C20	−0.1341 (6)	0.9075 (3)	0.1181 (3)	0.0841 (12)
H20A	−0.1327	0.8810	0.1742	0.126*
H20B	−0.2638	0.9272	0.1057	0.126*
H20C	−0.0366	0.9791	0.1336	0.126*
C21	0.7364 (6)	0.4885 (4)	0.4255 (3)	0.0977 (14)
H21A	0.8506	0.5328	0.4108	0.146*
H21B	0.7706	0.4704	0.4841	0.146*
H21C	0.6301	0.5378	0.4384	0.146*
H2	0.3791 (16)	0.309 (3)	0.290 (3)	0.080*

	U11	U22	U33	U12	U13	U23
O1	0.0555 (14)	0.0899 (18)	0.111 (2)	0.0186 (12)	0.0232 (14)	0.0730 (17)
O2	0.0539 (15)	0.0793 (16)	0.118 (2)	0.0240 (13)	0.0139 (14)	0.0555 (15)
O3	0.0596 (17)	0.0795 (18)	0.137 (3)	0.0214 (13)	−0.0033 (17)	0.0440 (18)
N1	0.0575 (18)	0.0537 (15)	0.062 (2)	0.0165 (13)	−0.0006 (15)	0.0301 (15)
N2	0.0473 (16)	0.0592 (16)	0.078 (2)	0.0149 (14)	0.0037 (16)	0.0420 (16)
N3	0.071 (2)	0.0561 (16)	0.077 (2)	0.0165 (15)	0.0121 (16)	0.0391 (16)
N4	0.0546 (18)	0.0831 (19)	0.108 (3)	0.0214 (15)	0.0239 (17)	0.070 (2)
C1	0.0493 (19)	0.0476 (17)	0.055 (2)	0.0121 (15)	0.0030 (16)	0.0239 (16)
C2	0.048 (2)	0.0527 (18)	0.051 (2)	0.0079 (15)	0.0085 (16)	0.0261 (17)
C3	0.0428 (19)	0.0593 (19)	0.071 (3)	0.0145 (16)	0.0099 (17)	0.0364 (18)
C4	0.050 (2)	0.0564 (18)	0.062 (2)	0.0109 (16)	0.0111 (17)	0.0329 (18)
C5	0.049 (2)	0.078 (2)	0.091 (3)	0.0170 (18)	0.0227 (19)	0.054 (2)
C6	0.047 (2)	0.064 (2)	0.078 (3)	0.0168 (16)	0.0093 (18)	0.036 (2)
C7	0.051 (2)	0.0497 (18)	0.058 (2)	0.0168 (16)	0.0002 (17)	0.0206 (17)
C8	0.046 (2)	0.0579 (19)	0.058 (2)	0.0172 (16)	0.0043 (17)	0.0248 (17)
C9	0.0447 (19)	0.0527 (18)	0.049 (2)	0.0133 (15)	0.0031 (16)	0.0233 (16)
C10	0.0446 (19)	0.071 (2)	0.070 (3)	0.0175 (16)	0.0158 (17)	0.038 (2)
C11	0.057 (2)	0.066 (2)	0.069 (3)	0.0114 (18)	0.0119 (19)	0.0401 (19)
C12	0.058 (2)	0.0480 (17)	0.050 (2)	0.0094 (16)	−0.0002 (17)	0.0233 (16)
C13	0.0447 (19)	0.061 (2)	0.075 (3)	0.0165 (16)	0.0112 (18)	0.0314 (19)
C14	0.050 (2)	0.0555 (18)	0.072 (3)	0.0133 (16)	0.0117 (18)	0.0353 (18)
C15	0.108 (3)	0.061 (2)	0.079 (3)	0.020 (2)	0.015 (2)	0.040 (2)
C16	0.071 (3)	0.069 (2)	0.109 (3)	0.0221 (19)	0.004 (2)	0.043 (2)
C17	0.079 (3)	0.083 (2)	0.094 (4)	0.025 (2)	0.017 (2)	0.050 (2)
C18	0.113 (4)	0.129 (4)	0.092 (4)	0.038 (3)	0.036 (3)	0.062 (3)
C19	0.058 (2)	0.066 (2)	0.069 (3)	0.0134 (17)	0.0033 (19)	0.038 (2)
C20	0.085 (3)	0.080 (3)	0.089 (3)	0.023 (2)	0.011 (2)	0.030 (2)
C21	0.101 (3)	0.090 (3)	0.114 (4)	0.029 (3)	0.024 (3)	0.046 (3)

O1—C2	1.362 (3)	C10—C11	1.373 (4)
O1—H1	0.8200	C10—H10	0.9300
O2—C8	1.239 (3)	C11—C12	1.397 (4)
O3—C21	1.397 (4)	C11—H11	0.9300
O3—H3	0.8200	C12—C13	1.404 (4)
N1—C7	1.281 (4)	C13—C14	1.383 (4)
N1—N2	1.396 (3)	C13—H13	0.9300
N2—C8	1.344 (4)	C14—H14	0.9300
N2—H2	0.900 (10)	C15—H15A	0.9600
N3—C12	1.368 (3)	C15—H15B	0.9600
N3—C16	1.441 (4)	C15—H15C	0.9600
N3—C15	1.454 (4)	C16—H16A	0.9600
N4—C4	1.381 (4)	C16—H16B	0.9600
N4—C19	1.448 (4)	C16—H16C	0.9600
N4—C17	1.504 (4)	C17—C18	1.469 (5)
C1—C6	1.396 (4)	C17—H17A	0.9700
C1—C2	1.403 (4)	C17—H17B	0.9700
C1—C7	1.441 (4)	C18—H18A	0.9600
C2—C3	1.384 (4)	C18—H18B	0.9600
C3—C4	1.395 (4)	C18—H18C	0.9600
C3—H3A	0.9300	C19—C20	1.501 (5)
C4—C5	1.404 (4)	C19—H19A	0.9700
C5—C6	1.369 (4)	C19—H19B	0.9700
C5—H5	0.9300	C20—H20A	0.9600
C6—H6	0.9300	C20—H20B	0.9600
C7—H7	0.9300	C20—H20C	0.9600
C8—C9	1.484 (4)	C21—H21A	0.9600
C9—C14	1.382 (4)	C21—H21B	0.9600
C9—C10	1.389 (4)	C21—H21C	0.9600
C2—O1—H1	109.5	C14—C13—C12	121.6 (3)
C21—O3—H3	109.5	C14—C13—H13	119.2
C7—N1—N2	115.4 (3)	C12—C13—H13	119.2
C8—N2—N1	121.0 (3)	C9—C14—C13	121.3 (3)
C8—N2—H2	129 (2)	C9—C14—H14	119.4
N1—N2—H2	110 (2)	C13—C14—H14	119.4
C12—N3—C16	121.6 (3)	N3—C15—H15A	109.5
C12—N3—C15	121.0 (3)	N3—C15—H15B	109.5
C16—N3—C15	117.3 (3)	H15A—C15—H15B	109.5
C4—N4—C19	122.5 (3)	N3—C15—H15C	109.5
C4—N4—C17	120.5 (3)	H15A—C15—H15C	109.5
C19—N4—C17	115.6 (2)	H15B—C15—H15C	109.5
C6—C1—C2	116.7 (3)	N3—C16—H16A	109.5
C6—C1—C7	119.4 (3)	N3—C16—H16B	109.5
C2—C1—C7	123.9 (3)	H16A—C16—H16B	109.5
O1—C2—C3	116.9 (3)	N3—C16—H16C	109.5
O1—C2—C1	121.8 (3)	H16A—C16—H16C	109.5
C3—C2—C1	121.3 (3)	H16B—C16—H16C	109.5
C2—C3—C4	121.2 (3)	C18—C17—N4	111.6 (3)
C2—C3—H3A	119.4	C18—C17—H17A	109.3
C4—C3—H3A	119.4	N4—C17—H17A	109.3
N4—C4—C3	121.3 (3)	C18—C17—H17B	109.3
N4—C4—C5	121.2 (3)	N4—C17—H17B	109.3
C3—C4—C5	117.5 (3)	H17A—C17—H17B	108.0
C6—C5—C4	120.9 (3)	C17—C18—H18A	109.5
C6—C5—H5	119.6	C17—C18—H18B	109.5
C4—C5—H5	119.6	H18A—C18—H18B	109.5
C5—C6—C1	122.4 (3)	C17—C18—H18C	109.5
C5—C6—H6	118.8	H18A—C18—H18C	109.5
C1—C6—H6	118.8	H18B—C18—H18C	109.5
N1—C7—C1	123.7 (3)	N4—C19—C20	112.6 (3)
N1—C7—H7	118.2	N4—C19—H19A	109.1
C1—C7—H7	118.2	C20—C19—H19A	109.1
O2—C8—N2	121.6 (3)	N4—C19—H19B	109.1
O2—C8—C9	121.1 (3)	C20—C19—H19B	109.1
N2—C8—C9	117.2 (3)	H19A—C19—H19B	107.8
C14—C9—C10	117.2 (3)	C19—C20—H20A	109.5
C14—C9—C8	124.7 (3)	C19—C20—H20B	109.5
C10—C9—C8	117.9 (3)	H20A—C20—H20B	109.5
C11—C10—C9	122.3 (3)	C19—C20—H20C	109.5
C11—C10—H10	118.8	H20A—C20—H20C	109.5
C9—C10—H10	118.8	H20B—C20—H20C	109.5
C10—C11—C12	121.0 (3)	O3—C21—H21A	109.5
C10—C11—H11	119.5	O3—C21—H21B	109.5
C12—C11—H11	119.5	H21A—C21—H21B	109.5
N3—C12—C11	121.6 (3)	O3—C21—H21C	109.5
N3—C12—C13	121.7 (3)	H21A—C21—H21C	109.5
C11—C12—C13	116.7 (3)	H21B—C21—H21C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3	0.90 (1)	2.07 (2)	2.936 (4)	160 (3)
O3—H3···O2i	0.82	1.84	2.661 (3)	177
O1—H1···N1	0.82	2.02	2.727 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3	0.90 (1)	2.07 (2)	2.936 (4)	160 (3)
O3—H3⋯O2i	0.82	1.84	2.661 (3)	177
O1—H1⋯N1	0.82	2.02	2.727 (3)	145

Symmetry code: (i) .