(E)-N′-[4-(Dimethyl­amino)­benzyl­idene]-4-methyl­benzohydrazide methanol monosolvate

Liu, H.; Cai, Y.; Wu, J.; Li, Z.; Li, G.

doi:10.1107/S1600536811029394

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2139

doi:10.1107/S1600536811029394

Open

access

(E)-N′-[4-(Dimethylamino)benzylidene]-4-methylbenzohydrazide methanol monosolvate

Huanyu Liu,^a ^* Yanchun Cai,^a Jianyong Wu,^a Zhuolin Li ^a and Guanwen Li ^a

^aSchool of Chemistry and Chemical Engineering, Guangdong Pharmaceutical University, Zhongshan 528453, People's Republic of China
^*Correspondence e-mail: liuhuanyu03@163.com

(Received 19 July 2011; accepted 20 July 2011; online 23 July 2011)

In the title compound, C₁₇H₁₉N₃O·CH₃OH, the hydrazone molecule exists in a trans geometry with respect to the methylidene 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 molecules.

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_r = 313.39
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.060
wR(F²) = 0.169
S = 1.00
3613 reflections
216 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) x-1, y, z.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811029394/hb6324sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811029394/hb6324Isup3.cml

checkCIF report

Comment top

Recently, the author has reported two new hydrazone compounds (Liu, 2010a,b). As a further study on these compounds, in the present work, the title new hydrazone compound, (I), which crystallised as a methanol solvate, is reported.

In the title compound (Fig. 1), the methanol molecule is linked to the hydrazone molecule through O—H···O and O—H···N hydrogen bonds (Table 1). The hydrazone molecule exists in a trans geometry with respect to the methylidene unit. The dihedral angle between the two substituted benzene rings is 42.6 (2)°. In the crystal structure, the hydrazone and the methanol molecules are linked through N—H···O and O—H···O, hydrogen bonds (Table 1), to form chains along the a axis (Fig. 2).

Related literature top

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

Experimental top

4-Dimethylaminobenzaldehyde (1.0 mmol, 153 mg) and 4-methylbenzohydrazide (1.0 mmol, 150 mg) were mixed in 50 mL methanol. The mixture was stirred at ambient temperature for 2 h and filtered. Colorless blocks of the title compound were formed by slow evaporation of the filtrate for a week.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Packing structure of the title compound, viewed along the c axis. Hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonding have been omitted.

(E)-N'-[4-(Dimethylamino)benzylidene]-4-methylbenzohydrazide methanol monosolvate top

Crystal data top

C₁₇H₁₉N₃O·CH₄O	Z = 2
M_r = 313.39	F(000) = 336
Triclinic, P1	D_x = 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

Data collection top

Bruker SMART CCD diffractometer	3613 independent reflections
Radiation source: fine-focus sealed tube	1755 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.0°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
T_min = 0.984, T_max = 0.990	k = −14→13
5975 measured reflections	l = −15→15

Refinement top

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(F_o²) + (0.0667P)²] where P = (F_o² + 2F_c²)/3
3613 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.16 e Å⁻³
1 restraint	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O·CH₄O	γ = 84.807 (3)°
M_r = 313.39	V = 856.7 (4) Å³
Triclinic, P1	Z = 2
a = 6.3874 (18) Å	Mo Kα radiation
b = 11.724 (3) Å	µ = 0.08 mm⁻¹
c = 11.975 (3) Å	T = 298 K
α = 78.830 (3)°	0.20 × 0.18 × 0.13 mm
β = 77.138 (3)°

Data collection top

Bruker SMART CCD diffractometer	3613 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1755 reflections with I > 2σ(I)
T_min = 0.984, T_max = 0.990	R_int = 0.030
5975 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.169	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.16 e Å⁻³
3613 reflections	Δρ_min = −0.19 e Å⁻³
216 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O·CH₄O
M_r	313.39
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.3874 (18), 11.724 (3), 11.975 (3)
α, β, γ (°)	78.830 (3), 77.138 (3), 84.807 (3)
V (Å³)	856.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.984, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	5975, 3613, 1755
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.169, 1.00
No. of reflections	3613
No. of parameters	216
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O2ⁱ	0.897 (10)	2.021 (11)	2.905 (3)	168 (2)
O2—H2···O1	0.82	1.92	2.720 (3)	166

Symmetry code: (i) x−1, y, z.

Acknowledgements

The work was supported by the Ten Hundred Thousand Project of the Bureau of Education of Guangdong Province, People's Republic of China.

References

Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Liu, H. (2010a). Acta Cryst. E66, o1582. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, H. (2010b). Acta Cryst. E66, o2026. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2139

doi:10.1107/S1600536811029394

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(E)-N′-[4-(Di­methyl­amino)­benzyl­­idene]-4-methyl­benzohydrazide methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(E)-N′-[4-(Dimethylamino)benzylidene]-4-methylbenzohydrazide methanol monosolvate