4-Dimethyl­amino-N′-(2-hy­droxy-4-meth­oxy­benzyl­idene)benzohydrazide methanol monosolvate

Sun, J.

doi:10.1107/S1600536812039906

organic compounds

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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page o2998

https://doi.org/10.1107/S1600536812039906

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4-Dimethylamino-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide methanol monosolvate

Jingya Sun ^a ^*

^aCollege of Marine Sciences, Zhejiang Ocean University, Zhoushan 316000, People's Republic of China
^*Correspondence e-mail: jingyasun2009@163.com

(Received 19 September 2012; accepted 19 September 2012; online 26 September 2012)

The asymmetric unit of the title compound, C₁₇H₁₉N₃O₃·CH₄O, comprises two Schiff base molecules and two methanol solvent molecules. The Schiff base molecules are approximately planar, with r.m.s. deviations from the planes defined by the non-H atoms of 0.107 and 0.154 Å, and with dihedral angles between the benzene rings of 4.49 (15) and 8.39 (15)°, respectively. This near-planarity is assisted by the formation of intramolecular O—H⋯N hydrogen bonds in each molecule. In the crystal, the components are linked by N—H⋯O and O—H⋯O hydrogen bonds to form chains along [010].

Related literature

For the properties of Schiff base compounds, see: Miura et al. (2009 ); Zhao et al. (2010 ); Karadağ et al. (2011 ); Bingöl Alpaslan et al. (2010 ). For the structure of a related Schiff base compound, see: Xu & Sun (2012 ).

Experimental

Crystal data

C₁₇H₁₉N₃O₃·CH₄O
M_r = 345.39
Monoclinic, P 2₁ /c
a = 7.7426 (17) Å
b = 23.473 (2) Å
c = 20.1975 (16) Å
β = 100.495 (2)°
V = 3609.3 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.985, T_max = 0.987
17259 measured reflections
6668 independent reflections
2824 reflections with I > 2σ(I)
R_int = 0.051

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.155
S = 0.99
6668 reflections
471 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.588 (3)	147
O4—H4⋯N4	0.82	1.93	2.649 (3)	146
O7—H7⋯O5	0.82	1.87	2.671 (3)	166
O8—H8⋯O2ⁱ	0.85 (1)	1.86 (1)	2.713 (3)	179 (4)
N5—H5⋯O8ⁱⁱ	0.91 (1)	2.02 (1)	2.892 (4)	161 (3)
N2—H2⋯O7ⁱⁱⁱ	0.90 (1)	2.01 (2)	2.876 (3)	159 (3)
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1.

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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812039906/hb6963sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039906/hb6963Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039906/hb6963Isup3.cml

checkCIF report

Comment top

The condensation reaction between aldehydes with organic primary amines readily forms Schiff bases containing the typical –C=N– groups (Miura et al., 2009; Zhao et al., 2010; Karadağ et al., 2011; Bingöl Alpaslan et al., 2010). As a continuation of our work on Schiff bases (Xu & Sun, 2012), in this paper, the title new compound (Fig. 1), prepared by the reaction of 4-methoxysalicylaldehyde with 4-dimethylaminobenzohydrazide in methanol, is reported.

The asymmetric unit of the compound comprises two Schiff base molecules, A and B, and two methanol molecules. The Schiff base molecules are approximately planar, with r.m.s. deviations from the planes defined by the non-hydrogen atoms of 0.107 and 0.154 Å, and with dihedral angles between the benzene rings of 4.49 (15) and 8.39 (15)° for molecules A and B, respectively. This planarity is assisted by the formation of intramolecular O—H···N hydrogen bonds (Table 1). In the crystal, (Fig. 2), Schiff base molecules are linked by methanol molecules through N—H···O and O—H···O hydrogen bonds (Table 1) to form chains.

Related literature top

For the properties of Schiff base compounds, see: Miura et al. (2009); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010). For the structure of a related Schiff base compound, see: Xu & Sun (2012).

Experimental top

4-Methoxysalicylaldehyde (1.0 mmol, 0.152 g) and 4-dimethylaminobenzohydrazide (1.0 mmol, 0.179 g) were refluxed for 30 min in 30 ml methanol, and cooled to room temperature to give colorless solid, which was isoloated by filtration. Colourless blocks were formed by recrystallization of the solid product in methanol.

Structure description top

For the properties of Schiff base compounds, see: Miura et al. (2009); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010). For the structure of a related Schiff base compound, see: Xu & Sun (2012).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compounds with 30% probability displacement ellipsoids. Hydrogen bonds are shown as dashed lines.
	Fig. 2. The molecular packing of the title compound. Hydrogen bonds are shown as dashed lines.

4-Dimethylamino-N'-(2-hydroxy-4-methoxybenzylidene)benzohydrazide methanol monosolvate top

Crystal data top

C₁₇H₁₉N₃O₃·CH₄O	F(000) = 1472
M_r = 345.39	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.7426 (17) Å	Cell parameters from 2668 reflections
b = 23.473 (2) Å	θ = 2.2–24.5°
c = 20.1975 (16) Å	µ = 0.09 mm⁻¹
β = 100.495 (2)°	T = 298 K
V = 3609.3 (9) Å³	Block, colorless
Z = 8	0.17 × 0.15 × 0.15 mm

Data collection top

Bruker SMART CCD diffractometer	6668 independent reflections
Radiation source: fine-focus sealed tube	2824 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.051
ω scans	θ_max = 25.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→9
T_min = 0.985, T_max = 0.987	k = −27→28
17259 measured reflections	l = −24→18

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ²(F_o²) + (0.0599P)²] where P = (F_o² + 2F_c²)/3
6668 reflections	(Δ/σ)_max < 0.001
471 parameters	Δρ_max = 0.15 e Å⁻³
3 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₁₉N₃O₃·CH₄O	V = 3609.3 (9) Å³
M_r = 345.39	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7426 (17) Å	µ = 0.09 mm⁻¹
b = 23.473 (2) Å	T = 298 K
c = 20.1975 (16) Å	0.17 × 0.15 × 0.15 mm
β = 100.495 (2)°

Data collection top

Bruker SMART CCD diffractometer	6668 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2824 reflections with I > 2σ(I)
T_min = 0.985, T_max = 0.987	R_int = 0.051
17259 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	3 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	Δρ_max = 0.15 e Å⁻³
6668 reflections	Δρ_min = −0.16 e Å⁻³
471 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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	0.3235 (3)	0.69983 (10)	0.90099 (12)	0.0533 (7)
N2	0.2735 (3)	0.69032 (10)	0.83293 (13)	0.0554 (7)
N3	−0.0477 (3)	0.68909 (11)	0.51462 (14)	0.0602 (7)
N4	0.3574 (3)	0.54206 (11)	0.19498 (13)	0.0604 (7)
N5	0.3984 (4)	0.55391 (11)	0.26325 (14)	0.0612 (7)
N6	0.7055 (4)	0.57953 (12)	0.58081 (15)	0.0696 (8)
O1	0.3173 (3)	0.75604 (9)	1.01077 (10)	0.0795 (7)
H1	0.2915	0.7486	0.9705	0.119*
O2	0.0887 (3)	0.76477 (9)	0.82402 (10)	0.0768 (7)
O3	0.6142 (3)	0.67343 (9)	1.21576 (11)	0.0720 (7)
O4	0.3881 (3)	0.49011 (10)	0.08124 (10)	0.0745 (7)
H4	0.4112	0.4965	0.1218	0.112*
O5	0.6060 (3)	0.48503 (10)	0.27995 (11)	0.0850 (8)
O6	0.0622 (3)	0.56832 (9)	−0.12049 (11)	0.0744 (7)
O7	0.4931 (3)	0.39331 (12)	0.20641 (14)	0.1030 (9)
H7	0.5105	0.4225	0.2290	0.154*
O8	1.1189 (4)	0.62247 (10)	0.29899 (13)	0.0873 (8)
C1	0.5549 (6)	0.71737 (17)	1.25440 (18)	0.1079 (14)
H1A	0.5902	0.7537	1.2395	0.162*
H1B	0.6052	0.7122	1.3011	0.162*
H1C	0.4291	0.7160	1.2488	0.162*
C2	0.5658 (4)	0.67530 (13)	1.14705 (16)	0.0512 (8)
C3	0.4607 (4)	0.71645 (13)	1.11238 (16)	0.0544 (8)
H3	0.4181	0.7460	1.1355	0.065*
C4	0.4182 (4)	0.71381 (12)	1.04274 (16)	0.0512 (8)
C5	0.4783 (4)	0.66948 (12)	1.00711 (15)	0.0454 (7)
C6	0.5853 (4)	0.62875 (12)	1.04426 (16)	0.0543 (8)
H6	0.6275	0.5988	1.0217	0.065*
C7	0.6304 (4)	0.63133 (13)	1.11282 (17)	0.0580 (9)
H7A	0.7038	0.6039	1.1363	0.070*
C8	0.4254 (4)	0.66316 (12)	0.93510 (15)	0.0506 (8)
H8A	0.4656	0.6323	0.9134	0.061*
C9	0.1532 (4)	0.72512 (13)	0.79644 (16)	0.0527 (8)
C10	0.1034 (4)	0.71363 (12)	0.72368 (15)	0.0473 (7)
C11	−0.0104 (4)	0.75043 (13)	0.68370 (16)	0.0564 (8)
H11	−0.0556	0.7813	0.7038	0.068*
C12	−0.0592 (4)	0.74306 (13)	0.61545 (16)	0.0568 (8)
H12	−0.1351	0.7692	0.5907	0.068*
C13	0.0023 (4)	0.69717 (12)	0.58217 (16)	0.0477 (8)
C14	0.1173 (4)	0.65991 (13)	0.62233 (16)	0.0557 (8)
H14	0.1623	0.6289	0.6024	0.067*
C15	0.1656 (4)	0.66801 (13)	0.69059 (16)	0.0569 (8)
H15	0.2423	0.6422	0.7155	0.068*
C16	−0.1515 (5)	0.73097 (15)	0.47253 (16)	0.0873 (12)
H16A	−0.2615	0.7361	0.4873	0.131*
H16B	−0.1727	0.7181	0.4266	0.131*
H16C	−0.0892	0.7665	0.4757	0.131*
C17	0.0302 (4)	0.64438 (14)	0.48000 (16)	0.0737 (10)
H17A	0.1555	0.6490	0.4880	0.111*
H17B	−0.0147	0.6467	0.4325	0.111*
H17C	0.0013	0.6079	0.4965	0.111*
C18	0.1354 (5)	0.52835 (15)	−0.16021 (16)	0.0790 (11)
H18A	0.2609	0.5322	−0.1518	0.118*
H18B	0.0903	0.5353	−0.2070	0.118*
H18C	0.1045	0.4905	−0.1487	0.118*
C19	0.1098 (4)	0.56550 (13)	−0.05226 (16)	0.0534 (8)
C20	0.2268 (4)	0.52696 (12)	−0.01860 (15)	0.0510 (8)
H20	0.2775	0.4997	−0.0424	0.061*
C21	0.2693 (4)	0.52866 (12)	0.05111 (15)	0.0489 (8)
C22	0.1962 (4)	0.56981 (13)	0.08811 (16)	0.0508 (8)
C23	0.0771 (4)	0.60764 (14)	0.05194 (18)	0.0653 (9)
H23	0.0263	0.6352	0.0753	0.078*
C24	0.0313 (4)	0.60594 (14)	−0.01701 (18)	0.0686 (10)
H24	−0.0508	0.6314	−0.0397	0.082*
C25	0.2455 (4)	0.57557 (14)	0.15955 (17)	0.0580 (9)
H25	0.1950	0.6045	0.1811	0.070*
C26	0.5289 (4)	0.52472 (15)	0.30257 (17)	0.0611 (9)
C27	0.5723 (4)	0.54179 (13)	0.37413 (15)	0.0506 (8)
C28	0.6851 (4)	0.50770 (13)	0.41801 (18)	0.0608 (9)
H28	0.7325	0.4756	0.4011	0.073*
C29	0.7299 (4)	0.51937 (14)	0.48550 (18)	0.0628 (9)
H29	0.8064	0.4952	0.5131	0.075*
C30	0.6623 (4)	0.56715 (13)	0.51346 (17)	0.0538 (8)
C31	0.5490 (4)	0.60199 (13)	0.46922 (16)	0.0587 (9)
H31	0.5019	0.6343	0.4859	0.070*
C32	0.5057 (4)	0.58973 (13)	0.40179 (16)	0.0582 (8)
H32	0.4301	0.6140	0.3738	0.070*
C33	0.8215 (5)	0.54243 (16)	0.62615 (17)	0.0867 (12)
H33A	0.7738	0.5046	0.6236	0.130*
H33B	0.8325	0.5564	0.6714	0.130*
H33C	0.9351	0.5418	0.6135	0.130*
C34	0.6210 (5)	0.62570 (16)	0.61016 (16)	0.0859 (12)
H34A	0.6260	0.6597	0.5842	0.129*
H34B	0.6804	0.6320	0.6556	0.129*
H34C	0.5006	0.6160	0.6101	0.129*
C35	0.3141 (6)	0.38195 (18)	0.19206 (19)	0.1043 (13)
H35A	0.2725	0.3744	0.2332	0.156*
H35B	0.2929	0.3493	0.1631	0.156*
H35C	0.2530	0.4143	0.1700	0.156*
C36	0.9621 (5)	0.59350 (15)	0.29735 (18)	0.0885 (12)
H36A	0.9487	0.5843	0.3424	0.133*
H36B	0.9630	0.5591	0.2718	0.133*
H36C	0.8660	0.6171	0.2767	0.133*
H5	0.332 (3)	0.5805 (10)	0.2794 (14)	0.080*
H2	0.322 (4)	0.6604 (9)	0.8149 (14)	0.080*
H8	1.111 (4)	0.6578 (5)	0.3071 (16)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0622 (17)	0.0529 (17)	0.0454 (17)	0.0059 (14)	0.0117 (14)	0.0018 (13)
N2	0.0665 (18)	0.0524 (17)	0.0481 (18)	0.0108 (14)	0.0130 (14)	0.0002 (14)
N3	0.0622 (18)	0.0633 (18)	0.0543 (19)	−0.0036 (15)	0.0084 (15)	−0.0047 (15)
N4	0.0623 (18)	0.0714 (19)	0.0503 (18)	−0.0068 (15)	0.0176 (15)	−0.0111 (15)
N5	0.065 (2)	0.070 (2)	0.0523 (19)	0.0044 (16)	0.0185 (15)	−0.0103 (15)
N6	0.073 (2)	0.075 (2)	0.058 (2)	−0.0117 (17)	0.0062 (16)	0.0013 (17)
O1	0.0999 (18)	0.0718 (16)	0.0644 (16)	0.0451 (14)	0.0085 (15)	0.0004 (13)
O2	0.1041 (19)	0.0646 (15)	0.0652 (16)	0.0290 (14)	0.0249 (13)	−0.0010 (12)
O3	0.0746 (16)	0.0834 (17)	0.0538 (16)	0.0110 (13)	0.0011 (12)	−0.0018 (13)
O4	0.0840 (17)	0.0817 (16)	0.0571 (14)	0.0341 (14)	0.0109 (13)	0.0050 (13)
O5	0.0789 (17)	0.0893 (18)	0.0877 (18)	0.0206 (15)	0.0171 (14)	−0.0301 (14)
O6	0.0779 (16)	0.0812 (17)	0.0595 (17)	0.0227 (13)	0.0001 (13)	−0.0020 (13)
O7	0.0803 (19)	0.111 (2)	0.106 (2)	0.0428 (17)	−0.0134 (15)	−0.0483 (17)
O8	0.0804 (18)	0.0752 (17)	0.111 (2)	0.0111 (17)	0.0290 (15)	−0.0145 (17)
C1	0.141 (4)	0.122 (3)	0.061 (3)	0.038 (3)	0.018 (2)	−0.025 (2)
C2	0.0460 (19)	0.056 (2)	0.051 (2)	0.0013 (16)	0.0081 (16)	0.0001 (17)
C3	0.054 (2)	0.052 (2)	0.058 (2)	0.0100 (16)	0.0113 (17)	−0.0076 (17)
C4	0.0509 (19)	0.0454 (19)	0.057 (2)	0.0111 (16)	0.0084 (16)	0.0018 (16)
C5	0.0436 (18)	0.0411 (18)	0.052 (2)	0.0047 (14)	0.0102 (15)	0.0003 (15)
C6	0.054 (2)	0.0452 (19)	0.064 (2)	0.0073 (16)	0.0128 (17)	−0.0025 (17)
C7	0.055 (2)	0.051 (2)	0.065 (2)	0.0115 (16)	0.0036 (18)	0.0029 (17)
C8	0.054 (2)	0.0438 (19)	0.057 (2)	0.0027 (16)	0.0184 (17)	−0.0041 (16)
C9	0.059 (2)	0.048 (2)	0.054 (2)	0.0070 (17)	0.0181 (18)	0.0089 (17)
C10	0.0499 (19)	0.0454 (19)	0.049 (2)	0.0026 (15)	0.0161 (15)	0.0003 (16)
C11	0.057 (2)	0.053 (2)	0.061 (2)	0.0087 (16)	0.0156 (17)	0.0002 (17)
C12	0.056 (2)	0.054 (2)	0.059 (2)	0.0055 (16)	0.0054 (17)	0.0075 (17)
C13	0.0464 (19)	0.0447 (19)	0.053 (2)	−0.0072 (15)	0.0131 (16)	−0.0031 (16)
C14	0.058 (2)	0.051 (2)	0.058 (2)	0.0076 (17)	0.0125 (17)	−0.0030 (17)
C15	0.057 (2)	0.057 (2)	0.056 (2)	0.0081 (17)	0.0094 (17)	0.0034 (17)
C16	0.108 (3)	0.088 (3)	0.060 (3)	0.008 (2)	0.003 (2)	0.007 (2)
C17	0.079 (3)	0.077 (2)	0.067 (2)	−0.010 (2)	0.019 (2)	−0.018 (2)
C18	0.086 (3)	0.092 (3)	0.060 (2)	0.011 (2)	0.013 (2)	−0.015 (2)
C19	0.053 (2)	0.054 (2)	0.052 (2)	0.0014 (17)	0.0064 (17)	−0.0031 (17)
C20	0.0523 (19)	0.0474 (19)	0.055 (2)	0.0057 (16)	0.0135 (16)	−0.0053 (16)
C21	0.0458 (19)	0.052 (2)	0.050 (2)	0.0017 (16)	0.0113 (16)	0.0011 (16)
C22	0.0448 (19)	0.055 (2)	0.055 (2)	0.0002 (16)	0.0167 (16)	−0.0076 (17)
C23	0.067 (2)	0.063 (2)	0.068 (3)	0.0169 (19)	0.0171 (19)	−0.0124 (19)
C24	0.065 (2)	0.067 (2)	0.072 (3)	0.0197 (19)	0.0073 (19)	−0.004 (2)
C25	0.055 (2)	0.062 (2)	0.061 (2)	−0.0026 (18)	0.0235 (18)	−0.0105 (18)
C26	0.055 (2)	0.064 (2)	0.068 (2)	−0.0046 (19)	0.0207 (19)	−0.010 (2)
C27	0.0464 (19)	0.053 (2)	0.055 (2)	−0.0017 (16)	0.0147 (16)	−0.0066 (17)
C28	0.059 (2)	0.045 (2)	0.079 (3)	−0.0008 (17)	0.0142 (19)	−0.0073 (19)
C29	0.055 (2)	0.058 (2)	0.073 (3)	0.0027 (17)	0.0046 (19)	0.0102 (19)
C30	0.0457 (19)	0.057 (2)	0.059 (2)	−0.0125 (17)	0.0114 (17)	0.0021 (19)
C31	0.060 (2)	0.055 (2)	0.062 (2)	0.0021 (17)	0.0131 (18)	−0.0107 (18)
C32	0.059 (2)	0.057 (2)	0.057 (2)	0.0045 (17)	0.0085 (17)	−0.0022 (17)
C33	0.083 (3)	0.102 (3)	0.069 (3)	−0.013 (2)	−0.001 (2)	0.021 (2)
C34	0.091 (3)	0.108 (3)	0.061 (2)	−0.011 (3)	0.018 (2)	−0.015 (2)
C35	0.104 (3)	0.127 (4)	0.080 (3)	0.014 (3)	0.014 (2)	−0.001 (3)
C36	0.090 (3)	0.080 (3)	0.089 (3)	−0.003 (2)	0.000 (2)	−0.017 (2)

Geometric parameters (Å, º) top

N1—C8	1.280 (3)	C12—H12	0.9300
N1—N2	1.377 (3)	C13—C14	1.397 (4)
N2—C9	1.352 (4)	C14—C15	1.374 (4)
N2—H2	0.903 (10)	C14—H14	0.9300
N3—C13	1.362 (3)	C15—H15	0.9300
N3—C16	1.444 (4)	C16—H16A	0.9600
N3—C17	1.452 (4)	C16—H16B	0.9600
N4—C25	1.287 (4)	C16—H16C	0.9600
N4—N5	1.386 (3)	C17—H17A	0.9600
N5—C26	1.352 (4)	C17—H17B	0.9600
N5—H5	0.905 (10)	C17—H17C	0.9600
N6—C30	1.371 (4)	C18—H18A	0.9600
N6—C34	1.448 (4)	C18—H18B	0.9600
N6—C33	1.451 (4)	C18—H18C	0.9600
O1—C4	1.351 (3)	C19—C20	1.370 (4)
O1—H1	0.8200	C19—C24	1.391 (4)
O2—C9	1.236 (3)	C20—C21	1.387 (4)
O3—C2	1.371 (3)	C20—H20	0.9300
O3—C1	1.419 (4)	C21—C22	1.402 (4)
O4—C21	1.353 (3)	C22—C23	1.388 (4)
O4—H4	0.8200	C22—C25	1.430 (4)
O5—C26	1.238 (3)	C23—C24	1.373 (4)
O6—C19	1.362 (3)	C23—H23	0.9300
O6—C18	1.418 (3)	C24—H24	0.9300
O7—C35	1.389 (4)	C25—H25	0.9300
O7—H7	0.8200	C26—C27	1.478 (4)
O8—C36	1.387 (4)	C27—C28	1.381 (4)
O8—H8	0.848 (10)	C27—C32	1.396 (4)
C1—H1A	0.9600	C28—C29	1.372 (4)
C1—H1B	0.9600	C28—H28	0.9300
C1—H1C	0.9600	C29—C30	1.399 (4)
C2—C3	1.370 (4)	C29—H29	0.9300
C2—C7	1.385 (4)	C30—C31	1.397 (4)
C3—C4	1.386 (4)	C31—C32	1.373 (4)
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.393 (4)	C32—H32	0.9300
C5—C6	1.392 (4)	C33—H33A	0.9600
C5—C8	1.445 (4)	C33—H33B	0.9600
C6—C7	1.366 (4)	C33—H33C	0.9600
C6—H6	0.9300	C34—H34A	0.9600
C7—H7A	0.9300	C34—H34B	0.9600
C8—H8A	0.9300	C34—H34C	0.9600
C9—C10	1.475 (4)	C35—H35A	0.9600
C10—C11	1.384 (4)	C35—H35B	0.9600
C10—C15	1.394 (4)	C35—H35C	0.9600
C11—C12	1.372 (4)	C36—H36A	0.9600
C11—H11	0.9300	C36—H36B	0.9600
C12—C13	1.398 (4)	C36—H36C	0.9600

C8—N1—N2	117.5 (3)	H17A—C17—H17B	109.5
C9—N2—N1	119.1 (3)	N3—C17—H17C	109.5
C9—N2—H2	123 (2)	H17A—C17—H17C	109.5
N1—N2—H2	118 (2)	H17B—C17—H17C	109.5
C13—N3—C16	121.4 (3)	O6—C18—H18A	109.5
C13—N3—C17	121.1 (3)	O6—C18—H18B	109.5
C16—N3—C17	116.4 (3)	H18A—C18—H18B	109.5
C25—N4—N5	116.1 (3)	O6—C18—H18C	109.5
C26—N5—N4	119.6 (3)	H18A—C18—H18C	109.5
C26—N5—H5	123 (2)	H18B—C18—H18C	109.5
N4—N5—H5	117 (2)	O6—C19—C20	124.5 (3)
C30—N6—C34	121.2 (3)	O6—C19—C24	114.9 (3)
C30—N6—C33	120.7 (3)	C20—C19—C24	120.5 (3)
C34—N6—C33	117.7 (3)	C19—C20—C21	119.9 (3)
C4—O1—H1	109.5	C19—C20—H20	120.1
C2—O3—C1	118.5 (3)	C21—C20—H20	120.1
C21—O4—H4	109.5	O4—C21—C20	117.0 (3)
C19—O6—C18	118.6 (2)	O4—C21—C22	121.9 (3)
C35—O7—H7	109.5	C20—C21—C22	121.1 (3)
C36—O8—H8	113 (2)	C23—C22—C21	117.0 (3)
O3—C1—H1A	109.5	C23—C22—C25	120.0 (3)
O3—C1—H1B	109.5	C21—C22—C25	122.9 (3)
H1A—C1—H1B	109.5	C24—C23—C22	122.6 (3)
O3—C1—H1C	109.5	C24—C23—H23	118.7
H1A—C1—H1C	109.5	C22—C23—H23	118.7
H1B—C1—H1C	109.5	C23—C24—C19	118.8 (3)
C3—C2—O3	124.6 (3)	C23—C24—H24	120.6
C3—C2—C7	120.3 (3)	C19—C24—H24	120.6
O3—C2—C7	115.1 (3)	N4—C25—C22	122.1 (3)
C2—C3—C4	119.7 (3)	N4—C25—H25	118.9
C2—C3—H3	120.1	C22—C25—H25	118.9
C4—C3—H3	120.1	O5—C26—N5	121.6 (3)
O1—C4—C3	117.5 (3)	O5—C26—C27	121.7 (3)
O1—C4—C5	121.3 (3)	N5—C26—C27	116.7 (3)
C3—C4—C5	121.2 (3)	C28—C27—C32	116.5 (3)
C6—C5—C4	117.2 (3)	C28—C27—C26	118.4 (3)
C6—C5—C8	120.3 (3)	C32—C27—C26	125.1 (3)
C4—C5—C8	122.4 (3)	C29—C28—C27	122.5 (3)
C7—C6—C5	122.2 (3)	C29—C28—H28	118.7
C7—C6—H6	118.9	C27—C28—H28	118.7
C5—C6—H6	118.9	C28—C29—C30	121.0 (3)
C6—C7—C2	119.3 (3)	C28—C29—H29	119.5
C6—C7—H7A	120.3	C30—C29—H29	119.5
C2—C7—H7A	120.3	N6—C30—C31	121.4 (3)
N1—C8—C5	120.4 (3)	N6—C30—C29	121.9 (3)
N1—C8—H8A	119.8	C31—C30—C29	116.7 (3)
C5—C8—H8A	119.8	C32—C31—C30	121.6 (3)
O2—C9—N2	120.3 (3)	C32—C31—H31	119.2
O2—C9—C10	122.2 (3)	C30—C31—H31	119.2
N2—C9—C10	117.5 (3)	C31—C32—C27	121.6 (3)
C11—C10—C15	116.0 (3)	C31—C32—H32	119.2
C11—C10—C9	119.4 (3)	C27—C32—H32	119.2
C15—C10—C9	124.6 (3)	N6—C33—H33A	109.5
C12—C11—C10	122.5 (3)	N6—C33—H33B	109.5
C12—C11—H11	118.8	H33A—C33—H33B	109.5
C10—C11—H11	118.8	N6—C33—H33C	109.5
C11—C12—C13	121.6 (3)	H33A—C33—H33C	109.5
C11—C12—H12	119.2	H33B—C33—H33C	109.5
C13—C12—H12	119.2	N6—C34—H34A	109.5
N3—C13—C14	121.9 (3)	N6—C34—H34B	109.5
N3—C13—C12	121.9 (3)	H34A—C34—H34B	109.5
C14—C13—C12	116.1 (3)	N6—C34—H34C	109.5
C15—C14—C13	121.6 (3)	H34A—C34—H34C	109.5
C15—C14—H14	119.2	H34B—C34—H34C	109.5
C13—C14—H14	119.2	O7—C35—H35A	109.5
C14—C15—C10	122.2 (3)	O7—C35—H35B	109.5
C14—C15—H15	118.9	H35A—C35—H35B	109.5
C10—C15—H15	118.9	O7—C35—H35C	109.5
N3—C16—H16A	109.5	H35A—C35—H35C	109.5
N3—C16—H16B	109.5	H35B—C35—H35C	109.5
H16A—C16—H16B	109.5	O8—C36—H36A	109.5
N3—C16—H16C	109.5	O8—C36—H36B	109.5
H16A—C16—H16C	109.5	H36A—C36—H36B	109.5
H16B—C16—H16C	109.5	O8—C36—H36C	109.5
N3—C17—H17A	109.5	H36A—C36—H36C	109.5
N3—C17—H17B	109.5	H36B—C36—H36C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.588 (3)	147
O4—H4···N4	0.82	1.93	2.649 (3)	146
O7—H7···O5	0.82	1.87	2.671 (3)	166
O8—H8···O2ⁱ	0.85 (1)	1.86 (1)	2.713 (3)	179 (4)
N5—H5···O8ⁱⁱ	0.91 (1)	2.02 (1)	2.892 (4)	161 (3)
N2—H2···O7ⁱⁱⁱ	0.90 (1)	2.01 (2)	2.876 (3)	159 (3)

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₃·CH₄O
M_r	345.39
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	7.7426 (17), 23.473 (2), 20.1975 (16)
β (°)	100.495 (2)
V (Å³)	3609.3 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.17 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	17259, 6668, 2824
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.155, 0.99
No. of reflections	6668
No. of parameters	471
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.588 (3)	147
O4—H4···N4	0.82	1.93	2.649 (3)	146
O7—H7···O5	0.82	1.87	2.671 (3)	166
O8—H8···O2ⁱ	0.848 (10)	1.864 (11)	2.713 (3)	179 (4)
N5—H5···O8ⁱⁱ	0.905 (10)	2.023 (14)	2.892 (4)	161 (3)
N2—H2···O7ⁱⁱⁱ	0.903 (10)	2.014 (15)	2.876 (3)	159 (3)

Symmetry codes: (i) x+1, −y+3/2, z−1/2; (ii) x−1, y, z; (iii) −x+1, −y+1, −z+1.

Acknowledgements

This work was supported by the Open Foundation from Ocean Fishery Science and Technology in the Most Important Subjects of Zhejiang (project No. 20110217).

References

Bingöl Alpaslan, Y., Alpaslan, G., Ağar, A. & Işık, Ş. (2010). Acta Cryst. E66, o510. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Karadağ, A. T., Atalay, Ş. & Genç, H. (2011). Acta Cryst. E67, o95. Web of Science CrossRef IUCr Journals Google Scholar
Miura, Y., Aritake, Y. & Akitsu, T. (2009). Acta Cryst. E65, o2381. 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
Xu, H. & Sun, J. (2012). Acta Cryst. E68, o1042. CSD CrossRef IUCr Journals Google Scholar
Zhao, L., Cao, D. & Cui, J. (2010). Acta Cryst. E66, o2204. Web of Science CSD CrossRef IUCr Journals Google Scholar

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

4-Di­methyl­amino-N′-(2-hy­dr­oxy-4-meth­­oxy­benzyl­­idene)benzohydrazide methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-Dimethylamino-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide methanol monosolvate