(E)-N'-[4-(Dimethyl-amino)-benzyl-idene]-4-methyl-benzohydrazide methanol monosolvate.

In the title compound, C(17)H(19)N(3)O·CH(3)OH, the hydrazone mol-ecule exists in a trans geometry with respect to the methyl-idene unit and the dihedral angle between the two substituted benzene rings is 42.6 (2)°. In the crystal, the components are linked through N-H⋯O and O-H⋯O hydrogen bonds, forming [100] chains of alternating hydrazone and methanol mol-ecules.

Related literature

For the hydrazone compounds reported by one of the authors recently and background refereences, see: Liu (2010a ▶,b ▶).

Experimental

Crystal data

C17H19N3O·CH4O

M = 313.39

Triclinic,

a = 6.3874 (18) Å

b = 11.724 (3) Å

c = 11.975 (3) Å

α = 78.830 (3)°

β = 77.138 (3)°

γ = 84.807 (3)°

V = 856.7 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 298 K

0.20 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.984, T max = 0.990

5975 measured reflections

3613 independent reflections

1755 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.169

S = 1.00

3613 reflections

216 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029394/hb6324sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029394/hb6324Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811029394/hb6324Isup3.cml

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

C17H19N3O·CH4O	Z = 2
Mr = 313.39	F(000) = 336
Triclinic, P1	Dx = 1.215 Mg m−3
a = 6.3874 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.724 (3) Å	Cell parameters from 744 reflections
c = 11.975 (3) Å	θ = 2.6–24.9°
α = 78.830 (3)°	µ = 0.08 mm−1
β = 77.138 (3)°	T = 298 K
γ = 84.807 (3)°	Block, colorless
V = 856.7 (4) Å3	0.20 × 0.18 × 0.13 mm

Bruker SMART CCD diffractometer	3613 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
Tmin = 0.984, Tmax = 0.990	k = −14→13
5975 measured reflections	l = −15→15

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0667P)2] where P = (Fo2 + 2Fc2)/3
3613 reflections	(Δ/σ)max < 0.001
216 parameters	Δρmax = 0.16 e Å−3
1 restraint	Δρmin = −0.19 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
N1	0.4251 (3)	0.17760 (17)	0.23171 (17)	0.0519 (6)
N2	0.2884 (3)	0.26788 (18)	0.27010 (18)	0.0518 (5)
N3	0.7692 (4)	−0.29356 (18)	0.03356 (18)	0.0603 (6)
O1	0.5681 (3)	0.37103 (15)	0.27273 (17)	0.0699 (6)
O2	0.8472 (3)	0.19729 (18)	0.3439 (2)	0.0945 (7)
H2	0.7518	0.2406	0.3205	0.142*
C1	0.6665 (4)	−0.2025 (2)	0.0848 (2)	0.0493 (6)
C2	0.4491 (4)	−0.2032 (2)	0.1361 (2)	0.0584 (7)
H2A	0.3721	−0.2677	0.1391	0.070*
C3	0.3463 (4)	−0.1095 (2)	0.1824 (2)	0.0595 (7)
H3	0.2001	−0.1121	0.2154	0.071*
C4	0.4524 (4)	−0.0118 (2)	0.1816 (2)	0.0498 (6)
C5	0.6711 (4)	−0.0127 (2)	0.1337 (2)	0.0563 (7)
H5	0.7481	0.0511	0.1331	0.068*
C6	0.7761 (4)	−0.1051 (2)	0.0874 (2)	0.0557 (7)
H6	0.9233	−0.1033	0.0571	0.067*
C7	0.3337 (4)	0.0872 (2)	0.2259 (2)	0.0547 (7)
H7	0.1853	0.0847	0.2511	0.066*
C8	0.3731 (4)	0.3636 (2)	0.2844 (2)	0.0494 (6)
C9	0.2198 (4)	0.4615 (2)	0.31429 (19)	0.0450 (6)
C10	0.0261 (4)	0.4838 (2)	0.2788 (2)	0.0518 (7)
H10	−0.0156	0.4341	0.2368	0.062*
C11	−0.1058 (4)	0.5789 (2)	0.3052 (2)	0.0566 (7)
H11	−0.2332	0.5937	0.2783	0.068*
C12	−0.0529 (5)	0.6528 (2)	0.3707 (2)	0.0541 (7)
C13	0.1388 (5)	0.6292 (2)	0.4075 (2)	0.0601 (7)
H13	0.1772	0.6769	0.4525	0.072*
C14	0.2749 (4)	0.5360 (2)	0.3787 (2)	0.0534 (7)
H14	0.4051	0.5231	0.4029	0.064*
C15	−0.2024 (5)	0.7539 (2)	0.4031 (2)	0.0797 (9)
H15A	−0.1317	0.8013	0.4390	0.119*
H15B	−0.3298	0.7250	0.4567	0.119*
H15C	−0.2408	0.7996	0.3343	0.119*
C16	0.6496 (5)	−0.3900 (2)	0.0267 (2)	0.0713 (8)
H16A	0.6002	−0.4333	0.1035	0.107*
H16B	0.7407	−0.4398	−0.0206	0.107*
H16C	0.5283	−0.3608	−0.0073	0.107*
C17	0.9965 (5)	−0.2948 (2)	−0.0162 (3)	0.0775 (9)
H17A	1.0262	−0.2307	−0.0798	0.116*
H17B	1.0406	−0.3666	−0.0439	0.116*
H17C	1.0740	−0.2879	0.0421	0.116*
C18	0.7566 (5)	0.1029 (3)	0.4231 (3)	0.0921 (11)
H18A	0.8683	0.0469	0.4421	0.138*
H18B	0.6613	0.0677	0.3895	0.138*
H18C	0.6774	0.1288	0.4925	0.138*
H2B	0.1469 (18)	0.257 (2)	0.292 (2)	0.080*

	U11	U22	U33	U12	U13	U23
N1	0.0519 (13)	0.0437 (12)	0.0603 (14)	0.0045 (11)	−0.0138 (10)	−0.0106 (10)
N2	0.0470 (13)	0.0442 (12)	0.0652 (14)	0.0003 (11)	−0.0110 (11)	−0.0142 (10)
N3	0.0649 (16)	0.0474 (13)	0.0717 (15)	−0.0017 (12)	−0.0149 (12)	−0.0181 (11)
O1	0.0476 (12)	0.0561 (12)	0.1090 (16)	−0.0009 (9)	−0.0189 (10)	−0.0201 (10)
O2	0.0519 (13)	0.0742 (15)	0.147 (2)	0.0031 (11)	−0.0245 (13)	0.0062 (14)
C1	0.0572 (17)	0.0415 (14)	0.0500 (15)	−0.0037 (13)	−0.0151 (12)	−0.0048 (12)
C2	0.0613 (18)	0.0485 (16)	0.0673 (18)	−0.0154 (14)	−0.0106 (14)	−0.0129 (13)
C3	0.0467 (16)	0.0586 (17)	0.0754 (19)	−0.0063 (13)	−0.0093 (13)	−0.0198 (15)
C4	0.0513 (16)	0.0435 (15)	0.0556 (16)	−0.0021 (12)	−0.0122 (12)	−0.0100 (12)
C5	0.0564 (18)	0.0445 (15)	0.0668 (18)	−0.0111 (13)	−0.0067 (14)	−0.0102 (13)
C6	0.0454 (15)	0.0507 (16)	0.0707 (18)	−0.0079 (13)	−0.0059 (13)	−0.0148 (14)
C7	0.0490 (16)	0.0510 (16)	0.0647 (18)	−0.0015 (13)	−0.0106 (13)	−0.0137 (13)
C8	0.0491 (16)	0.0465 (15)	0.0519 (15)	−0.0034 (13)	−0.0116 (12)	−0.0057 (12)
C9	0.0453 (15)	0.0428 (14)	0.0447 (14)	−0.0027 (12)	−0.0084 (11)	−0.0037 (11)
C10	0.0550 (17)	0.0513 (16)	0.0525 (15)	−0.0004 (13)	−0.0147 (13)	−0.0142 (12)
C11	0.0539 (17)	0.0612 (17)	0.0537 (16)	0.0036 (14)	−0.0137 (13)	−0.0080 (13)
C12	0.0670 (19)	0.0428 (15)	0.0464 (15)	0.0046 (13)	−0.0049 (13)	−0.0044 (12)
C13	0.076 (2)	0.0510 (16)	0.0545 (17)	−0.0121 (15)	−0.0065 (14)	−0.0174 (13)
C14	0.0561 (16)	0.0490 (16)	0.0579 (16)	−0.0079 (13)	−0.0166 (13)	−0.0088 (13)
C15	0.101 (3)	0.0611 (19)	0.0695 (19)	0.0140 (17)	−0.0032 (17)	−0.0179 (15)
C16	0.091 (2)	0.0502 (17)	0.076 (2)	−0.0128 (16)	−0.0134 (16)	−0.0202 (14)
C17	0.073 (2)	0.073 (2)	0.088 (2)	−0.0007 (17)	−0.0077 (17)	−0.0311 (17)
C18	0.090 (3)	0.074 (2)	0.112 (3)	0.004 (2)	−0.035 (2)	−0.005 (2)

N1—C7	1.275 (3)	C9—C10	1.383 (3)
N1—N2	1.392 (3)	C9—C14	1.386 (3)
N2—C8	1.344 (3)	C10—C11	1.378 (3)
N2—H2B	0.897 (10)	C10—H10	0.9300
N3—C1	1.376 (3)	C11—C12	1.384 (3)
N3—C17	1.441 (3)	C11—H11	0.9300
N3—C16	1.445 (3)	C12—C13	1.379 (4)
O1—C8	1.232 (3)	C12—C15	1.508 (3)
O2—C18	1.387 (3)	C13—C14	1.382 (3)
O2—H2	0.8200	C13—H13	0.9300
C1—C2	1.388 (3)	C14—H14	0.9300
C1—C6	1.402 (3)	C15—H15A	0.9600
C2—C3	1.374 (3)	C15—H15B	0.9600
C2—H2A	0.9300	C15—H15C	0.9600
C3—C4	1.381 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.387 (3)	C16—H16C	0.9600
C4—C7	1.450 (3)	C17—H17A	0.9600
C5—C6	1.366 (3)	C17—H17B	0.9600
C5—H5	0.9300	C17—H17C	0.9600
C6—H6	0.9300	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.485 (3)	C18—H18C	0.9600
C7—N1—N2	115.7 (2)	C9—C10—H10	119.7
C8—N2—N1	119.3 (2)	C10—C11—C12	121.4 (3)
C8—N2—H2B	121.7 (17)	C10—C11—H11	119.3
N1—N2—H2B	118.6 (17)	C12—C11—H11	119.3
C1—N3—C17	121.3 (2)	C13—C12—C11	117.7 (2)
C1—N3—C16	120.4 (2)	C13—C12—C15	121.2 (3)
C17—N3—C16	118.3 (2)	C11—C12—C15	121.1 (3)
C18—O2—H2	109.5	C12—C13—C14	121.3 (2)
N3—C1—C2	121.3 (2)	C12—C13—H13	119.4
N3—C1—C6	121.7 (2)	C14—C13—H13	119.4
C2—C1—C6	117.0 (2)	C13—C14—C9	120.7 (3)
C3—C2—C1	120.8 (2)	C13—C14—H14	119.6
C3—C2—H2A	119.6	C9—C14—H14	119.6
C1—C2—H2A	119.6	C12—C15—H15A	109.5
C2—C3—C4	122.3 (2)	C12—C15—H15B	109.5
C2—C3—H3	118.9	H15A—C15—H15B	109.5
C4—C3—H3	118.9	C12—C15—H15C	109.5
C3—C4—C5	116.9 (2)	H15A—C15—H15C	109.5
C3—C4—C7	120.0 (2)	H15B—C15—H15C	109.5
C5—C4—C7	123.0 (2)	N3—C16—H16A	109.5
C6—C5—C4	121.6 (2)	N3—C16—H16B	109.5
C6—C5—H5	119.2	H16A—C16—H16B	109.5
C4—C5—H5	119.2	N3—C16—H16C	109.5
C5—C6—C1	121.3 (2)	H16A—C16—H16C	109.5
C5—C6—H6	119.3	H16B—C16—H16C	109.5
C1—C6—H6	119.3	N3—C17—H17A	109.5
N1—C7—C4	122.5 (2)	N3—C17—H17B	109.5
N1—C7—H7	118.7	H17A—C17—H17B	109.5
C4—C7—H7	118.7	N3—C17—H17C	109.5
O1—C8—N2	122.2 (2)	H17A—C17—H17C	109.5
O1—C8—C9	121.1 (2)	H17B—C17—H17C	109.5
N2—C8—C9	116.8 (2)	O2—C18—H18A	109.5
C10—C9—C14	118.1 (2)	O2—C18—H18B	109.5
C10—C9—C8	123.2 (2)	H18A—C18—H18B	109.5
C14—C9—C8	118.6 (2)	O2—C18—H18C	109.5
C11—C10—C9	120.7 (2)	H18A—C18—H18C	109.5
C11—C10—H10	119.7	H18B—C18—H18C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2i	0.90 (1)	2.02 (1)	2.905 (3)	168 (2)
O2—H2···O1	0.82	1.92	2.720 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O2i	0.90 (1)	2.02 (1)	2.905 (3)	168 (2)
O2—H2⋯O1	0.82	1.92	2.720 (3)	166

Symmetry code: (i) .