N′-(3,5-Dichloro-2-hy­droxy­benzyl­idene)-4-(dimethyl­amino)­benzohydrazide methanol monosolvate

Xu, H.; Sun, J.

doi:10.1107/S1600536812010148

organic compounds

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Volume 68| Part 4| April 2012| Page o1042

doi:10.1107/S1600536812010148

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N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate

Huanzhi Xu ^a and Jingya Sun ^a ^*

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

(Received 7 March 2012; accepted 7 March 2012; online 10 March 2012)

The title compound, C₁₆H₁₅Cl₂N₃O₂·CH₃OH, a Schiff base molecule, is prepared by the reaction of 3,5-dichlorosalicylaldehyde with 4-dimethylaminobenzohydrazide in methanol. The Schiff base molecule is approximately planar, with a mean deviation from the least-squares plane defined by the non-H atoms of 0.0452 (3) Å, and with a dihedral angle between the benzene rings of 4.2 (3)°. This planarity is assisted by the formation of an intramolecular O—H⋯N hydrogen bond. In the crystal, adjacent Schiff base molecules are linked by two methanol molecules through N—H⋯O and O—H⋯O hydrogen bonds, forming dimers.

Related literature

For the preparation of Schiff base compounds by the condensation reaction between aldehydes with organic primary amines, see: Miura et al. (2009 ); Zhao et al. (2010 ); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010 ). For standard bond lengths, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₆H₁₅Cl₂N₃O₂·CH₄O
M_r = 384.25
Monoclinic, P 2₁ /n
a = 7.6498 (15) Å
b = 14.338 (3) Å
c = 16.884 (2) Å
β = 103.076 (2)°
V = 1803.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.38 mm⁻¹
T = 298 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.952, T_max = 0.963
8311 measured reflections
3238 independent reflections
1790 reflections with I > 2σ(I)
R_int = 0.072

Refinement

R[F² > 2σ(F²)] = 0.079
wR(F²) = 0.180
S = 1.03
3238 reflections
231 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O3ⁱ	0.86	2.10	2.848 (5)	145
O1—H1⋯N1	0.82	1.91	2.600 (5)	141
O3—H3⋯O2	0.82	1.97	2.771 (5)	166
Symmetry code: (i) -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: 10.1107/S1600536812010148/qm2057sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812010148/qm2057Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812010148/qm2057Isup3.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). In this paper, the new title compound (Fig. 1), was prepared by the reaction of 3,5-dichlorosalicylaldehyde with 4-dimethylaminobenzohydrazide in methanol.

The asymmetric unit comprises a Schiff base molecule and a methanol molecule. The Schiff base molecule is approximately planar, with mean deviation from the least squares plane defined by the non-hydrogen atoms of 0.0452 (3) Å, and with the dihedral angle between the two benzene rings of 4.2 (3)°. This planarity is assisted by the formation of an intramolecular O1—H1···N1 hydrogen bond (Table 1). All the bond lengths are within normal ranges (Allen et al., 1987). In the crystal structure adjacent Schiff base molecules are linked by two methanol molecules through intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) to form a dimer (Fig. 2).

Related literature top

For the preparation of Schiff base compounds by the condensation reaction between aldehydes with organic primary amines, see: Miura et al. (2009); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental top

3,5-Dichlorosalicylaldehyde (1.0 mmol, 0.190 g) and 4-dimethylaminobenzohydrazide (1.0 mmol, 0.179 g) were refluxed for 30 min in 30 ml me thanol, and cooled to room temperature to give colorless solid, which was isoloated by filtration. Single crystals of the title compound were formed by recrystallization of the solid product in methanol.

Structure description top

For the preparation of Schiff base compounds by the condensation reaction between aldehydes with organic primary amines, see: Miura et al. (2009); Zhao et al. (2010); Karadağ et al. (2011); Bingöl Alpaslan et al. (2010). For standard bond lengths, see: Allen et al. (1987).

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 atom labels and the 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.

N'-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate top

Crystal data top

C₁₆H₁₅Cl₂N₃O₂·CH₄O	F(000) = 800
M_r = 384.25	D_x = 1.415 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.6498 (15) Å	Cell parameters from 2546 reflections
b = 14.338 (3) Å	θ = 2.5–28.3°
c = 16.884 (2) Å	µ = 0.38 mm⁻¹
β = 103.076 (2)°	T = 298 K
V = 1803.8 (5) Å³	Block, colorless
Z = 4	0.13 × 0.12 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3238 independent reflections
Radiation source: fine-focus sealed tube	1790 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.072
ω scans	θ_max = 25.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.952, T_max = 0.963	k = −16→17
8311 measured reflections	l = −13→20

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)] = 0.079	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.180	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0664P)² + 0.8315P] where P = (F_o² + 2F_c²)/3
3238 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₅Cl₂N₃O₂·CH₄O	V = 1803.8 (5) Å³
M_r = 384.25	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.6498 (15) Å	µ = 0.38 mm⁻¹
b = 14.338 (3) Å	T = 298 K
c = 16.884 (2) Å	0.13 × 0.12 × 0.10 mm
β = 103.076 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3238 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1790 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.963	R_int = 0.072
8311 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.079	0 restraints
wR(F²) = 0.180	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
3238 reflections	Δρ_min = −0.22 e Å⁻³
231 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
Cl1	0.4325 (2)	0.29209 (10)	0.15198 (9)	0.0674 (5)
Cl2	0.4175 (2)	0.65692 (11)	0.07222 (9)	0.0719 (5)
N1	0.2957 (5)	0.4874 (3)	0.4015 (2)	0.0450 (10)
N2	0.2686 (5)	0.5167 (3)	0.4749 (2)	0.0431 (10)
H2	0.2702	0.5751	0.4864	0.052*
N3	0.1064 (6)	0.5808 (3)	0.8296 (2)	0.0490 (11)
O1	0.3448 (5)	0.3581 (2)	0.3007 (2)	0.0564 (10)
H1	0.3013	0.3780	0.3376	0.085*
O2	0.2453 (5)	0.3677 (2)	0.5161 (2)	0.0530 (10)
O3	0.5727 (5)	0.3035 (2)	0.4941 (2)	0.0608 (10)
H3	0.4685	0.3145	0.4960	0.091*
C1	0.3425 (6)	0.5229 (3)	0.2711 (3)	0.0394 (12)
C2	0.3621 (6)	0.4282 (3)	0.2505 (3)	0.0420 (12)
C3	0.4009 (6)	0.4078 (4)	0.1756 (3)	0.0483 (13)
C4	0.4178 (6)	0.4767 (4)	0.1208 (3)	0.0463 (13)
H4	0.4441	0.4616	0.0712	0.056*
C5	0.3950 (6)	0.5682 (4)	0.1411 (3)	0.0481 (13)
C6	0.3577 (6)	0.5909 (4)	0.2145 (3)	0.0474 (13)
H6	0.3422	0.6532	0.2266	0.057*
C7	0.3097 (6)	0.5495 (3)	0.3482 (3)	0.0407 (12)
H7	0.2984	0.6123	0.3599	0.049*
C8	0.2386 (6)	0.4510 (4)	0.5302 (3)	0.0388 (12)
C9	0.1976 (6)	0.4892 (3)	0.6054 (3)	0.0363 (11)
C10	0.1902 (6)	0.4268 (3)	0.6673 (3)	0.0408 (12)
H10	0.2087	0.3637	0.6592	0.049*
C11	0.1562 (6)	0.4551 (3)	0.7403 (3)	0.0436 (12)
H11	0.1497	0.4109	0.7799	0.052*
C12	0.1311 (6)	0.5505 (3)	0.7556 (3)	0.0358 (11)
C13	0.1359 (6)	0.6129 (3)	0.6922 (3)	0.0455 (12)
H13	0.1173	0.6761	0.6996	0.055*
C14	0.1672 (6)	0.5830 (3)	0.6193 (3)	0.0427 (12)
H14	0.1681	0.6263	0.5784	0.051*
C15	0.0961 (8)	0.5155 (4)	0.8937 (3)	0.0577 (15)
H15A	0.0012	0.4716	0.8743	0.087*
H15B	0.0723	0.5487	0.9395	0.087*
H15C	0.2080	0.4827	0.9098	0.087*
C16	0.0752 (7)	0.6783 (4)	0.8461 (3)	0.0591 (15)
H16A	0.1787	0.7145	0.8425	0.089*
H16B	0.0538	0.6841	0.8997	0.089*
H16C	−0.0274	0.7007	0.8069	0.089*
C17	0.5794 (7)	0.2197 (4)	0.4506 (3)	0.0619 (16)
H17A	0.7002	0.1964	0.4626	0.093*
H17B	0.5411	0.2315	0.3934	0.093*
H17C	0.5016	0.1743	0.4665	0.093*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0718 (10)	0.0608 (9)	0.0729 (10)	0.0044 (7)	0.0235 (8)	−0.0241 (8)
Cl2	0.0840 (11)	0.0797 (11)	0.0536 (9)	−0.0156 (9)	0.0192 (8)	0.0149 (8)
N1	0.047 (3)	0.048 (3)	0.040 (3)	0.000 (2)	0.011 (2)	−0.009 (2)
N2	0.057 (3)	0.039 (2)	0.033 (2)	−0.002 (2)	0.010 (2)	−0.0098 (19)
N3	0.071 (3)	0.037 (2)	0.046 (3)	−0.001 (2)	0.026 (2)	0.000 (2)
O1	0.078 (3)	0.045 (2)	0.048 (2)	0.0047 (19)	0.018 (2)	0.0026 (18)
O2	0.074 (2)	0.035 (2)	0.055 (2)	0.0019 (17)	0.0234 (19)	−0.0095 (17)
O3	0.069 (2)	0.041 (2)	0.077 (3)	−0.0039 (19)	0.025 (2)	−0.0124 (19)
C1	0.035 (3)	0.046 (3)	0.034 (3)	−0.002 (2)	0.001 (2)	−0.005 (2)
C2	0.043 (3)	0.049 (3)	0.031 (3)	−0.002 (2)	0.002 (2)	0.001 (2)
C3	0.042 (3)	0.058 (3)	0.047 (3)	−0.002 (2)	0.014 (2)	−0.013 (3)
C4	0.037 (3)	0.070 (4)	0.032 (3)	−0.002 (2)	0.007 (2)	0.000 (3)
C5	0.044 (3)	0.062 (4)	0.036 (3)	−0.016 (3)	0.004 (2)	0.006 (3)
C6	0.050 (3)	0.044 (3)	0.046 (3)	−0.008 (2)	0.005 (2)	0.000 (3)
C7	0.042 (3)	0.040 (3)	0.039 (3)	0.002 (2)	0.007 (2)	−0.004 (2)
C8	0.029 (3)	0.050 (3)	0.037 (3)	−0.003 (2)	0.008 (2)	0.000 (3)
C9	0.036 (3)	0.038 (3)	0.038 (3)	−0.002 (2)	0.015 (2)	−0.003 (2)
C10	0.040 (3)	0.032 (3)	0.053 (3)	0.002 (2)	0.015 (2)	−0.002 (2)
C11	0.047 (3)	0.043 (3)	0.043 (3)	0.005 (2)	0.016 (2)	0.008 (2)
C12	0.036 (3)	0.036 (3)	0.037 (3)	−0.005 (2)	0.013 (2)	−0.005 (2)
C13	0.055 (3)	0.033 (3)	0.052 (3)	0.000 (2)	0.020 (3)	−0.003 (3)
C14	0.058 (3)	0.032 (3)	0.043 (3)	0.004 (2)	0.021 (2)	0.005 (2)
C15	0.070 (4)	0.063 (4)	0.042 (3)	0.003 (3)	0.015 (3)	−0.001 (3)
C16	0.068 (4)	0.054 (3)	0.062 (4)	0.001 (3)	0.030 (3)	−0.011 (3)
C17	0.074 (4)	0.053 (4)	0.063 (4)	0.009 (3)	0.024 (3)	−0.009 (3)

Geometric parameters (Å, º) top

Cl1—C3	1.736 (5)	C6—H6	0.9300
Cl2—C5	1.758 (5)	C7—H7	0.9300
N1—C7	1.288 (6)	C8—C9	1.480 (6)
N1—N2	1.367 (5)	C9—C10	1.387 (6)
N2—C8	1.381 (6)	C9—C14	1.394 (6)
N2—H2	0.8600	C10—C11	1.378 (6)
N3—C12	1.374 (6)	C10—H10	0.9300
N3—C15	1.447 (6)	C11—C12	1.414 (6)
N3—C16	1.456 (6)	C11—H11	0.9300
O1—C2	1.342 (5)	C12—C13	1.402 (6)
O1—H1	0.8200	C13—C14	1.374 (6)
O2—C8	1.222 (5)	C13—H13	0.9300
O3—C17	1.415 (6)	C14—H14	0.9300
O3—H3	0.8200	C15—H15A	0.9600
C1—C6	1.388 (6)	C15—H15B	0.9600
C1—C2	1.417 (6)	C15—H15C	0.9600
C1—C7	1.433 (6)	C16—H16A	0.9600
C2—C3	1.393 (6)	C16—H16B	0.9600
C3—C4	1.379 (7)	C16—H16C	0.9600
C4—C5	1.378 (7)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.372 (7)	C17—H17C	0.9600

C7—N1—N2	118.3 (4)	C14—C9—C8	125.3 (4)
N1—N2—C8	119.1 (4)	C11—C10—C9	122.2 (4)
N1—N2—H2	120.5	C11—C10—H10	118.9
C8—N2—H2	120.5	C9—C10—H10	118.9
C12—N3—C15	121.1 (4)	C10—C11—C12	120.6 (4)
C12—N3—C16	122.6 (4)	C10—C11—H11	119.7
C15—N3—C16	116.1 (4)	C12—C11—H11	119.7
C2—O1—H1	109.5	N3—C12—C13	121.7 (4)
C17—O3—H3	109.5	N3—C12—C11	121.6 (4)
C6—C1—C2	118.3 (4)	C13—C12—C11	116.7 (4)
C6—C1—C7	119.8 (5)	C14—C13—C12	121.6 (4)
C2—C1—C7	121.9 (5)	C14—C13—H13	119.2
O1—C2—C3	119.2 (5)	C12—C13—H13	119.2
O1—C2—C1	122.1 (4)	C13—C14—C9	121.5 (5)
C3—C2—C1	118.7 (5)	C13—C14—H14	119.3
C4—C3—C2	122.0 (5)	C9—C14—H14	119.3
C4—C3—Cl1	119.4 (4)	N3—C15—H15A	109.5
C2—C3—Cl1	118.6 (4)	N3—C15—H15B	109.5
C5—C4—C3	118.6 (5)	H15A—C15—H15B	109.5
C5—C4—H4	120.7	N3—C15—H15C	109.5
C3—C4—H4	120.7	H15A—C15—H15C	109.5
C6—C5—C4	120.9 (5)	H15B—C15—H15C	109.5
C6—C5—Cl2	119.9 (4)	N3—C16—H16A	109.5
C4—C5—Cl2	119.2 (4)	N3—C16—H16B	109.5
C5—C6—C1	121.5 (5)	H16A—C16—H16B	109.5
C5—C6—H6	119.3	N3—C16—H16C	109.5
C1—C6—H6	119.3	H16A—C16—H16C	109.5
N1—C7—C1	120.7 (4)	H16B—C16—H16C	109.5
N1—C7—H7	119.7	O3—C17—H17A	109.5
C1—C7—H7	119.7	O3—C17—H17B	109.5
O2—C8—N2	120.9 (4)	H17A—C17—H17B	109.5
O2—C8—C9	123.7 (4)	O3—C17—H17C	109.5
N2—C8—C9	115.4 (4)	H17A—C17—H17C	109.5
C10—C9—C14	117.3 (4)	H17B—C17—H17C	109.5
C10—C9—C8	117.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O3ⁱ	0.86	2.10	2.848 (5)	145
O1—H1···N1	0.82	1.91	2.600 (5)	141
O3—H3···O2	0.82	1.97	2.771 (5)	166

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅Cl₂N₃O₂·CH₄O
M_r	384.25
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.6498 (15), 14.338 (3), 16.884 (2)
β (°)	103.076 (2)
V (Å³)	1803.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.952, 0.963
No. of measured, independent and observed [I > 2σ(I)] reflections	8311, 3238, 1790
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.079, 0.180, 1.03
No. of reflections	3238
No. of parameters	231
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22

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
N2—H2···O3ⁱ	0.86	2.10	2.848 (5)	145.3
O1—H1···N1	0.82	1.91	2.600 (5)	141.2
O3—H3···O2	0.82	1.97	2.771 (5)	165.9

Symmetry code: (i) −x+1, −y+1, −z+1.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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Volume 68| Part 4| April 2012| Page o1042

doi:10.1107/S1600536812010148

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

N′-(3,5-Di­chloro-2-hy­dr­oxy­benzyl­­idene)-4-(di­methyl­amino)­benzohydrazide methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

N′-(3,5-Dichloro-2-hydroxybenzylidene)-4-(dimethylamino)benzohydrazide methanol monosolvate