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

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ISSN: 2056-9890

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

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[Liu, H. (2010a). Acta Cryst. E66, o1582.],b[Liu, H. (2010b). Acta Cryst. E66, o2026.]).

[Scheme 1]

Experimental

Crystal data
  • C17H19N3O·CH4O

  • Mr = 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[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.984, Tmax = 0.990

  • 5975 measured reflections

  • 3613 independent reflections

  • 1755 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.16 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1998[Bruker (1998). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The amino hydrogen atom was located in an electronic density map and refined isotropically, with the N—H distance restrained to 0.90 (1)Å. Other hydrogen atoms were placed in calculated positions, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, and refined as riding with Uiso(H) = 1.2Ueq(C) and 1.5Ueq(O and methyl C).

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
[Figure 1] Fig. 1. Molecular structure of the title compound with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
[Figure 2] 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·CH4OZ = 2
Mr = 313.39F(000) = 336
Triclinic, P1Dx = 1.215 Mg m3
a = 6.3874 (18) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.724 (3) ÅCell parameters from 744 reflections
c = 11.975 (3) Åθ = 2.6–24.9°
α = 78.830 (3)°µ = 0.08 mm1
β = 77.138 (3)°T = 298 K
γ = 84.807 (3)°Block, colorless
V = 856.7 (4) Å30.20 × 0.18 × 0.13 mm
Data collection top
Bruker SMART CCD
diffractometer
3613 independent reflections
Radiation source: fine-focus sealed tube1755 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
ω scansθmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
h = 88
Tmin = 0.984, Tmax = 0.990k = 1413
5975 measured reflectionsl = 1515
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169H 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 parametersΔρmax = 0.16 e Å3
1 restraintΔρmin = 0.19 e Å3
Crystal data top
C17H19N3O·CH4Oγ = 84.807 (3)°
Mr = 313.39V = 856.7 (4) Å3
Triclinic, P1Z = 2
a = 6.3874 (18) ÅMo Kα radiation
b = 11.724 (3) ŵ = 0.08 mm1
c = 11.975 (3) ÅT = 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)
Tmin = 0.984, Tmax = 0.990Rint = 0.030
5975 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.169H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å3
3613 reflectionsΔρmin = 0.19 e Å3
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
xyzUiso*/Ueq
N10.4251 (3)0.17760 (17)0.23171 (17)0.0519 (6)
N20.2884 (3)0.26788 (18)0.27010 (18)0.0518 (5)
N30.7692 (4)0.29356 (18)0.03356 (18)0.0603 (6)
O10.5681 (3)0.37103 (15)0.27273 (17)0.0699 (6)
O20.8472 (3)0.19729 (18)0.3439 (2)0.0945 (7)
H20.75180.24060.32050.142*
C10.6665 (4)0.2025 (2)0.0848 (2)0.0493 (6)
C20.4491 (4)0.2032 (2)0.1361 (2)0.0584 (7)
H2A0.37210.26770.13910.070*
C30.3463 (4)0.1095 (2)0.1824 (2)0.0595 (7)
H30.20010.11210.21540.071*
C40.4524 (4)0.0118 (2)0.1816 (2)0.0498 (6)
C50.6711 (4)0.0127 (2)0.1337 (2)0.0563 (7)
H50.74810.05110.13310.068*
C60.7761 (4)0.1051 (2)0.0874 (2)0.0557 (7)
H60.92330.10330.05710.067*
C70.3337 (4)0.0872 (2)0.2259 (2)0.0547 (7)
H70.18530.08470.25110.066*
C80.3731 (4)0.3636 (2)0.2844 (2)0.0494 (6)
C90.2198 (4)0.4615 (2)0.31429 (19)0.0450 (6)
C100.0261 (4)0.4838 (2)0.2788 (2)0.0518 (7)
H100.01560.43410.23680.062*
C110.1058 (4)0.5789 (2)0.3052 (2)0.0566 (7)
H110.23320.59370.27830.068*
C120.0529 (5)0.6528 (2)0.3707 (2)0.0541 (7)
C130.1388 (5)0.6292 (2)0.4075 (2)0.0601 (7)
H130.17720.67690.45250.072*
C140.2749 (4)0.5360 (2)0.3787 (2)0.0534 (7)
H140.40510.52310.40290.064*
C150.2024 (5)0.7539 (2)0.4031 (2)0.0797 (9)
H15A0.13170.80130.43900.119*
H15B0.32980.72500.45670.119*
H15C0.24080.79960.33430.119*
C160.6496 (5)0.3900 (2)0.0267 (2)0.0713 (8)
H16A0.60020.43330.10350.107*
H16B0.74070.43980.02060.107*
H16C0.52830.36080.00730.107*
C170.9965 (5)0.2948 (2)0.0162 (3)0.0775 (9)
H17A1.02620.23070.07980.116*
H17B1.04060.36660.04390.116*
H17C1.07400.28790.04210.116*
C180.7566 (5)0.1029 (3)0.4231 (3)0.0921 (11)
H18A0.86830.04690.44210.138*
H18B0.66130.06770.38950.138*
H18C0.67740.12880.49250.138*
H2B0.1469 (18)0.257 (2)0.292 (2)0.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0519 (13)0.0437 (12)0.0603 (14)0.0045 (11)0.0138 (10)0.0106 (10)
N20.0470 (13)0.0442 (12)0.0652 (14)0.0003 (11)0.0110 (11)0.0142 (10)
N30.0649 (16)0.0474 (13)0.0717 (15)0.0017 (12)0.0149 (12)0.0181 (11)
O10.0476 (12)0.0561 (12)0.1090 (16)0.0009 (9)0.0189 (10)0.0201 (10)
O20.0519 (13)0.0742 (15)0.147 (2)0.0031 (11)0.0245 (13)0.0062 (14)
C10.0572 (17)0.0415 (14)0.0500 (15)0.0037 (13)0.0151 (12)0.0048 (12)
C20.0613 (18)0.0485 (16)0.0673 (18)0.0154 (14)0.0106 (14)0.0129 (13)
C30.0467 (16)0.0586 (17)0.0754 (19)0.0063 (13)0.0093 (13)0.0198 (15)
C40.0513 (16)0.0435 (15)0.0556 (16)0.0021 (12)0.0122 (12)0.0100 (12)
C50.0564 (18)0.0445 (15)0.0668 (18)0.0111 (13)0.0067 (14)0.0102 (13)
C60.0454 (15)0.0507 (16)0.0707 (18)0.0079 (13)0.0059 (13)0.0148 (14)
C70.0490 (16)0.0510 (16)0.0647 (18)0.0015 (13)0.0106 (13)0.0137 (13)
C80.0491 (16)0.0465 (15)0.0519 (15)0.0034 (13)0.0116 (12)0.0057 (12)
C90.0453 (15)0.0428 (14)0.0447 (14)0.0027 (12)0.0084 (11)0.0037 (11)
C100.0550 (17)0.0513 (16)0.0525 (15)0.0004 (13)0.0147 (13)0.0142 (12)
C110.0539 (17)0.0612 (17)0.0537 (16)0.0036 (14)0.0137 (13)0.0080 (13)
C120.0670 (19)0.0428 (15)0.0464 (15)0.0046 (13)0.0049 (13)0.0044 (12)
C130.076 (2)0.0510 (16)0.0545 (17)0.0121 (15)0.0065 (14)0.0174 (13)
C140.0561 (16)0.0490 (16)0.0579 (16)0.0079 (13)0.0166 (13)0.0088 (13)
C150.101 (3)0.0611 (19)0.0695 (19)0.0140 (17)0.0032 (17)0.0179 (15)
C160.091 (2)0.0502 (17)0.076 (2)0.0128 (16)0.0134 (16)0.0202 (14)
C170.073 (2)0.073 (2)0.088 (2)0.0007 (17)0.0077 (17)0.0311 (17)
C180.090 (3)0.074 (2)0.112 (3)0.004 (2)0.035 (2)0.005 (2)
Geometric parameters (Å, º) top
N1—C71.275 (3)C9—C101.383 (3)
N1—N21.392 (3)C9—C141.386 (3)
N2—C81.344 (3)C10—C111.378 (3)
N2—H2B0.897 (10)C10—H100.9300
N3—C11.376 (3)C11—C121.384 (3)
N3—C171.441 (3)C11—H110.9300
N3—C161.445 (3)C12—C131.379 (4)
O1—C81.232 (3)C12—C151.508 (3)
O2—C181.387 (3)C13—C141.382 (3)
O2—H20.8200C13—H130.9300
C1—C21.388 (3)C14—H140.9300
C1—C61.402 (3)C15—H15A0.9600
C2—C31.374 (3)C15—H15B0.9600
C2—H2A0.9300C15—H15C0.9600
C3—C41.381 (3)C16—H16A0.9600
C3—H30.9300C16—H16B0.9600
C4—C51.387 (3)C16—H16C0.9600
C4—C71.450 (3)C17—H17A0.9600
C5—C61.366 (3)C17—H17B0.9600
C5—H50.9300C17—H17C0.9600
C6—H60.9300C18—H18A0.9600
C7—H70.9300C18—H18B0.9600
C8—C91.485 (3)C18—H18C0.9600
C7—N1—N2115.7 (2)C9—C10—H10119.7
C8—N2—N1119.3 (2)C10—C11—C12121.4 (3)
C8—N2—H2B121.7 (17)C10—C11—H11119.3
N1—N2—H2B118.6 (17)C12—C11—H11119.3
C1—N3—C17121.3 (2)C13—C12—C11117.7 (2)
C1—N3—C16120.4 (2)C13—C12—C15121.2 (3)
C17—N3—C16118.3 (2)C11—C12—C15121.1 (3)
C18—O2—H2109.5C12—C13—C14121.3 (2)
N3—C1—C2121.3 (2)C12—C13—H13119.4
N3—C1—C6121.7 (2)C14—C13—H13119.4
C2—C1—C6117.0 (2)C13—C14—C9120.7 (3)
C3—C2—C1120.8 (2)C13—C14—H14119.6
C3—C2—H2A119.6C9—C14—H14119.6
C1—C2—H2A119.6C12—C15—H15A109.5
C2—C3—C4122.3 (2)C12—C15—H15B109.5
C2—C3—H3118.9H15A—C15—H15B109.5
C4—C3—H3118.9C12—C15—H15C109.5
C3—C4—C5116.9 (2)H15A—C15—H15C109.5
C3—C4—C7120.0 (2)H15B—C15—H15C109.5
C5—C4—C7123.0 (2)N3—C16—H16A109.5
C6—C5—C4121.6 (2)N3—C16—H16B109.5
C6—C5—H5119.2H16A—C16—H16B109.5
C4—C5—H5119.2N3—C16—H16C109.5
C5—C6—C1121.3 (2)H16A—C16—H16C109.5
C5—C6—H6119.3H16B—C16—H16C109.5
C1—C6—H6119.3N3—C17—H17A109.5
N1—C7—C4122.5 (2)N3—C17—H17B109.5
N1—C7—H7118.7H17A—C17—H17B109.5
C4—C7—H7118.7N3—C17—H17C109.5
O1—C8—N2122.2 (2)H17A—C17—H17C109.5
O1—C8—C9121.1 (2)H17B—C17—H17C109.5
N2—C8—C9116.8 (2)O2—C18—H18A109.5
C10—C9—C14118.1 (2)O2—C18—H18B109.5
C10—C9—C8123.2 (2)H18A—C18—H18B109.5
C14—C9—C8118.6 (2)O2—C18—H18C109.5
C11—C10—C9120.7 (2)H18A—C18—H18C109.5
C11—C10—H10119.7H18B—C18—H18C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O2i0.90 (1)2.02 (1)2.905 (3)168 (2)
O2—H2···O10.821.922.720 (3)166
Symmetry code: (i) x1, y, z.

Experimental details

Crystal data
Chemical formulaC17H19N3O·CH4O
Mr313.39
Crystal system, space groupTriclinic, 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)
V3)856.7 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.20 × 0.18 × 0.13
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1998)
Tmin, Tmax0.984, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
5975, 3613, 1755
Rint0.030
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.169, 1.00
No. of reflections3613
No. of parameters216
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
N2—H2B···O2i0.897 (10)2.021 (11)2.905 (3)168 (2)
O2—H2···O10.821.922.720 (3)166
Symmetry code: (i) x1, 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

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

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