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

Zhi, F.; Wang, R.; Zhang, Y.; Wang, Q.; Yang, Y.-L.

doi:10.1107/S1600536811039778

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2825

doi:10.1107/S1600536811039778

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

Feng Zhi,^a Rong Wang,^a Yi Zhang,^a Qiang Wang ^a and Yi-Lin Yang ^a ^*

^aThird Affiliated Hospital of Suzhou University, Changzhou 213000, People's Republic of China
^*Correspondence e-mail: yangyilin_szu@126.com

(Received 24 September 2011; accepted 28 September 2011; online 5 October 2011)

The title compound, C₁₅H₁₃ClN₂O₃·CH₃OH, was synthesized by the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-chlorobenzohydrazide in methanol. The Schiff base molecule displays a trans configuration with respect to the C=N and C—N bonds. The dihedral angle between the two benzene rings is 5.3 (2)°. In the crystal, molecules are linked by N—H⋯O and O—H⋯O hydrogen-bond interactions into chains running parallel to the a axis. An intramolecular O—H⋯N hydrogen bond is observed.

Related literature

For background to Schiff base compounds, see: Fan et al. (2007 ); Kim et al. (2005 ); Nimitsiriwat et al. (2004 ). For their biological activity, see: Chen et al. (1997 ); Ren et al. (2002 ). For related structures, see: Mohd Lair et al. (2009 ); Fun et al. (2008 ); Yang (2008 ); Zhi (2008 , 2009 ); Zhi & Yang (2007 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃·CH₄O
M_r = 336.77
Triclinic, $[P \overline 1]$
a = 6.570 (2) Å
b = 10.343 (3) Å
c = 12.707 (3) Å
α = 100.371 (2)°
β = 91.864 (2)°
γ = 101.663 (2)°
V = 829.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 K
0.17 × 0.13 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.959, T_max = 0.971
5945 measured reflections
3022 independent reflections
1724 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.144
S = 1.01
3022 reflections
216 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O2ⁱ	0.82	1.83	2.646 (3)	177
N2—H2⋯O4	0.90 (1)	2.00 (1)	2.876 (3)	163 (2)
O1—H1⋯N1	0.82	1.96	2.676 (3)	146
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT (Bruker, 2002); 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/S1600536811039778/rz2644sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039778/rz2644Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039778/rz2644Isup3.cml

checkCIF report

Comment top

In recent years, much attention has been focused on the synthesis, structures, and properties of Schiff base compounds (Fan et al., 2007; Kim et al., 2005; Nimitsiriwat et al., 2004). Some of the compounds have been found to have excellent pharmacological and antibacterial activity (Chen et al., 1997; Ren et al., 2002). We report herein the crystal structure of the title new Schiff base compound (Fig. 1) derived from the condensation reaction of 2-hydroxy-4-methoxybenzaldehyde with 4-chlorobenzohydrazide.

The asymmetric unit of the title compound contains a Schiff base molecule and a methanol molecule of crystallization. The Schiff base molecule displays a trans configuration with respect to the C═N and C–N bonds. There is an intramolecular O—H···N hydrogen bond in the molecule. The dihedral angle between the two benzene rings is 5.3 (2)°. All the bond lengths are within normal ranges and comparable to those in other similar compounds (Mohd Lair et al., 2009; Fun et al., 2008; Yang, 2008; Zhi, 2008; Zhi & Yang, 2007; Zhi, 2009). In the crystal (Fig. 2), molecules are linked by N—H···O and O—H···O hydrogen interactions into one-dimensional chains along the a axis (Table 1).

Related literature top

For background to Schiff base compounds, see: Fan et al. (2007); Kim et al. (2005); Nimitsiriwat et al. (2004). For their biological activity, see: Chen et al. (1997); Ren et al. (2002). For related structures, see: Mohd Lair et al. (2009); Fun et al. (2008); Yang (2008); Zhi (2008, 2009); Zhi & Yang (2007).

Experimental top

2-Hydroxy-4-methoxybenzaldehyde (0.01 mol, 1.52 g) and 4-chlorobenzohydrazide (0.01 mol, 1.71 g) were dissolved in methanol (50 ml). The mixture was stirred at room temperature to give a clear colourless solution. Crystals of the title compound were formed by slow evaporation of the solvent for several days at room temperature.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); 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. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. Intramolecular O—H···N hydrogen bond is shown as a dashed line.
	Fig. 2. Crystal packing of the title compound, viewed along the a axis. Intermolecular hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₁₅H₁₃ClN₂O₃·CH₄O	Z = 2
M_r = 336.77	F(000) = 352
Triclinic, P1	D_x = 1.348 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.570 (2) Å	Cell parameters from 1241 reflections
b = 10.343 (3) Å	θ = 2.3–24.5°
c = 12.707 (3) Å	µ = 0.25 mm⁻¹
α = 100.371 (2)°	T = 298 K
β = 91.864 (2)°	Block, colorless
γ = 101.663 (2)°	0.17 × 0.13 × 0.12 mm
V = 829.7 (4) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3022 independent reflections
Radiation source: fine-focus sealed tube	1724 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.959, T_max = 0.971	k = −12→12
5945 measured reflections	l = −15→13

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0633P)²] where P = (F_o² + 2F_c²)/3
3022 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.23 e Å⁻³
1 restraint	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₃·CH₄O	γ = 101.663 (2)°
M_r = 336.77	V = 829.7 (4) Å³
Triclinic, P1	Z = 2
a = 6.570 (2) Å	Mo Kα radiation
b = 10.343 (3) Å	µ = 0.25 mm⁻¹
c = 12.707 (3) Å	T = 298 K
α = 100.371 (2)°	0.17 × 0.13 × 0.12 mm
β = 91.864 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	3022 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1724 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.971	R_int = 0.038
5945 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	1 restraint
wR(F²) = 0.144	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.23 e Å⁻³
3022 reflections	Δρ_min = −0.17 e Å⁻³
216 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	0.45941 (17)	1.34163 (8)	0.04723 (7)	0.1057 (4)
N1	0.6218 (3)	0.69152 (19)	0.29276 (16)	0.0550 (6)
N2	0.5628 (3)	0.7970 (2)	0.25424 (18)	0.0544 (6)
O1	0.8829 (3)	0.55918 (18)	0.37185 (18)	0.0764 (6)
H1	0.8513	0.6186	0.3438	0.115*
O2	0.8950 (3)	0.91058 (17)	0.25849 (18)	0.0853 (7)
O3	0.5767 (3)	0.14043 (16)	0.46539 (16)	0.0715 (6)
O4	0.1182 (3)	0.72464 (19)	0.20964 (17)	0.0731 (6)
H4	0.0462	0.7810	0.2227	0.110*
C1	0.5106 (4)	0.4800 (2)	0.34710 (19)	0.0485 (6)
C2	0.7089 (4)	0.4662 (2)	0.3793 (2)	0.0506 (6)
C3	0.7361 (4)	0.3544 (2)	0.42035 (19)	0.0528 (7)
H3	0.8687	0.3472	0.4431	0.063*
C4	0.5660 (4)	0.2544 (2)	0.4272 (2)	0.0533 (7)
C5	0.3685 (4)	0.2649 (3)	0.3942 (2)	0.0652 (8)
H5	0.2542	0.1964	0.3976	0.078*
C6	0.3423 (4)	0.3768 (3)	0.3565 (2)	0.0634 (8)
H6	0.2084	0.3845	0.3366	0.076*
C7	0.4739 (4)	0.5964 (2)	0.30752 (19)	0.0538 (7)
H7	0.3371	0.6024	0.2921	0.065*
C8	0.7072 (4)	0.9011 (2)	0.2375 (2)	0.0565 (7)
C9	0.6350 (4)	1.0083 (2)	0.1913 (2)	0.0526 (7)
C10	0.7810 (5)	1.1221 (3)	0.1836 (2)	0.0669 (8)
H10	0.9185	1.1298	0.2084	0.080*
C11	0.7275 (5)	1.2247 (3)	0.1399 (2)	0.0759 (9)
H11	0.8277	1.3008	0.1355	0.091*
C12	0.5255 (5)	1.2130 (3)	0.1031 (2)	0.0680 (8)
C13	0.3780 (5)	1.1019 (3)	0.1095 (2)	0.0761 (9)
H13	0.2408	1.0951	0.0846	0.091*
C14	0.4322 (4)	0.9993 (3)	0.1531 (2)	0.0699 (8)
H14	0.3311	0.9233	0.1567	0.084*
C15	0.7748 (4)	0.1250 (3)	0.5037 (3)	0.0789 (9)
H15A	0.8623	0.1154	0.4449	0.118*
H15B	0.7574	0.0465	0.5356	0.118*
H15C	0.8382	0.2028	0.5563	0.118*
C16	0.0297 (6)	0.6290 (4)	0.1191 (3)	0.1093 (12)
H16A	0.0040	0.6737	0.0616	0.164*
H16B	−0.0994	0.5770	0.1358	0.164*
H16C	0.1236	0.5706	0.0978	0.164*
H2	0.4259 (18)	0.792 (3)	0.240 (2)	0.085 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1478 (9)	0.0832 (6)	0.1065 (7)	0.0441 (6)	0.0043 (6)	0.0498 (5)
N1	0.0538 (13)	0.0482 (12)	0.0692 (14)	0.0191 (11)	−0.0014 (11)	0.0188 (10)
N2	0.0448 (13)	0.0522 (12)	0.0731 (15)	0.0169 (11)	−0.0001 (11)	0.0227 (11)
O1	0.0478 (11)	0.0667 (12)	0.1210 (17)	−0.0033 (9)	−0.0109 (11)	0.0546 (11)
O2	0.0489 (12)	0.0643 (12)	0.148 (2)	0.0151 (10)	−0.0058 (12)	0.0321 (12)
O3	0.0582 (12)	0.0592 (11)	0.1055 (15)	0.0078 (9)	0.0026 (11)	0.0437 (10)
O4	0.0475 (11)	0.0716 (12)	0.1049 (16)	0.0173 (9)	−0.0006 (11)	0.0252 (11)
C1	0.0453 (15)	0.0491 (13)	0.0541 (16)	0.0143 (12)	0.0040 (12)	0.0129 (12)
C2	0.0464 (16)	0.0455 (13)	0.0609 (16)	0.0059 (12)	0.0044 (12)	0.0169 (12)
C3	0.0424 (15)	0.0513 (14)	0.0698 (18)	0.0128 (12)	0.0006 (13)	0.0226 (12)
C4	0.0535 (17)	0.0463 (14)	0.0641 (17)	0.0096 (13)	0.0067 (13)	0.0217 (12)
C5	0.0448 (16)	0.0615 (16)	0.093 (2)	0.0056 (13)	0.0075 (15)	0.0307 (15)
C6	0.0418 (15)	0.0650 (17)	0.089 (2)	0.0121 (13)	0.0052 (14)	0.0290 (15)
C7	0.0476 (16)	0.0541 (15)	0.0650 (18)	0.0177 (13)	0.0027 (13)	0.0175 (13)
C8	0.0472 (17)	0.0488 (15)	0.0755 (19)	0.0152 (13)	0.0041 (14)	0.0113 (13)
C9	0.0525 (16)	0.0473 (14)	0.0616 (17)	0.0157 (12)	0.0072 (13)	0.0133 (12)
C10	0.0622 (18)	0.0604 (17)	0.077 (2)	0.0061 (15)	−0.0002 (15)	0.0198 (15)
C11	0.091 (2)	0.0552 (17)	0.081 (2)	0.0040 (16)	0.0001 (18)	0.0276 (15)
C12	0.096 (3)	0.0573 (17)	0.0602 (18)	0.0267 (17)	0.0105 (17)	0.0236 (14)
C13	0.0632 (19)	0.080 (2)	0.102 (2)	0.0287 (16)	0.0104 (17)	0.0439 (18)
C14	0.0574 (19)	0.0624 (17)	0.100 (2)	0.0135 (14)	0.0084 (16)	0.0408 (16)
C15	0.071 (2)	0.0640 (17)	0.110 (2)	0.0128 (16)	−0.0042 (18)	0.0434 (17)
C16	0.090 (3)	0.138 (3)	0.095 (3)	0.024 (2)	−0.001 (2)	0.012 (2)

Geometric parameters (Å, º) top

Cl1—C12	1.736 (3)	C5—H5	0.9300
N1—C7	1.280 (3)	C6—H6	0.9300
N1—N2	1.390 (3)	C7—H7	0.9300
N2—C8	1.337 (3)	C8—C9	1.492 (3)
N2—H2	0.901 (10)	C9—C10	1.380 (3)
O1—C2	1.355 (3)	C9—C14	1.383 (4)
O1—H1	0.8200	C10—C11	1.382 (4)
O2—C8	1.235 (3)	C10—H10	0.9300
O3—C4	1.366 (3)	C11—C12	1.367 (4)
O3—C15	1.423 (3)	C11—H11	0.9300
O4—C16	1.398 (3)	C12—C13	1.362 (4)
O4—H4	0.8200	C13—C14	1.383 (4)
C1—C2	1.395 (3)	C13—H13	0.9300
C1—C6	1.397 (3)	C14—H14	0.9300
C1—C7	1.445 (3)	C15—H15A	0.9600
C2—C3	1.392 (3)	C15—H15B	0.9600
C3—C4	1.378 (3)	C15—H15C	0.9600
C3—H3	0.9300	C16—H16A	0.9600
C4—C5	1.382 (4)	C16—H16B	0.9600
C5—C6	1.369 (3)	C16—H16C	0.9600

C7—N1—N2	116.3 (2)	C10—C9—C14	117.9 (2)
C8—N2—N1	120.2 (2)	C10—C9—C8	118.0 (2)
C8—N2—H2	121.7 (18)	C14—C9—C8	124.1 (2)
N1—N2—H2	118.1 (18)	C9—C10—C11	121.5 (3)
C2—O1—H1	109.5	C9—C10—H10	119.2
C4—O3—C15	118.4 (2)	C11—C10—H10	119.2
C16—O4—H4	109.5	C12—C11—C10	119.2 (3)
C2—C1—C6	117.5 (2)	C12—C11—H11	120.4
C2—C1—C7	122.8 (2)	C10—C11—H11	120.4
C6—C1—C7	119.7 (2)	C13—C12—C11	120.6 (3)
O1—C2—C3	116.9 (2)	C13—C12—Cl1	120.3 (3)
O1—C2—C1	122.3 (2)	C11—C12—Cl1	119.1 (2)
C3—C2—C1	120.8 (2)	C12—C13—C14	120.0 (3)
C4—C3—C2	119.7 (2)	C12—C13—H13	120.0
C4—C3—H3	120.1	C14—C13—H13	120.0
C2—C3—H3	120.1	C9—C14—C13	120.8 (3)
O3—C4—C3	124.1 (2)	C9—C14—H14	119.6
O3—C4—C5	115.4 (2)	C13—C14—H14	119.6
C3—C4—C5	120.4 (2)	O3—C15—H15A	109.5
C6—C5—C4	119.5 (2)	O3—C15—H15B	109.5
C6—C5—H5	120.3	H15A—C15—H15B	109.5
C4—C5—H5	120.3	O3—C15—H15C	109.5
C5—C6—C1	122.0 (2)	H15A—C15—H15C	109.5
C5—C6—H6	119.0	H15B—C15—H15C	109.5
C1—C6—H6	119.0	O4—C16—H16A	109.5
N1—C7—C1	122.7 (2)	O4—C16—H16B	109.5
N1—C7—H7	118.6	H16A—C16—H16B	109.5
C1—C7—H7	118.6	O4—C16—H16C	109.5
O2—C8—N2	122.4 (2)	H16A—C16—H16C	109.5
O2—C8—C9	119.8 (2)	H16B—C16—H16C	109.5
N2—C8—C9	117.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O2ⁱ	0.82	1.83	2.646 (3)	177
N2—H2···O4	0.90 (1)	2.00 (1)	2.876 (3)	163 (2)
O1—H1···N1	0.82	1.96	2.676 (3)	146

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₃·CH₄O
M_r	336.77
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.570 (2), 10.343 (3), 12.707 (3)
α, β, γ (°)	100.371 (2), 91.864 (2), 101.663 (2)
V (Å³)	829.7 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.17 × 0.13 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.959, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	5945, 3022, 1724
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.144, 1.01
No. of reflections	3022
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)	0.23, −0.17

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), 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
O4—H4···O2ⁱ	0.82	1.83	2.646 (3)	176.8
N2—H2···O4	0.901 (10)	2.000 (13)	2.876 (3)	163 (2)
O1—H1···N1	0.82	1.96	2.676 (3)	145.5

Symmetry code: (i) x−1, y, z.

Acknowledgements

Financial support from the Third Affiliated Hospital of Suzhou University is acknowledged.

References

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Volume 67| Part 11| November 2011| Page o2825

doi:10.1107/S1600536811039778

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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