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

Weng, Q.; Zhao, L.

doi:10.1107/S1600536809009659

organic compounds

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Volume 65| Part 4| April 2009| Page o808

doi:10.1107/S1600536809009659

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

Qianfeng Weng ^a ^* and Lei Zhao ^a

^aCollege of Chemistry and Chemical Engineering, Liaoning Normal University, Dalian 116029, People's Republic of China
^*Correspondence e-mail: qianfeng_weng@163.com

(Received 16 March 2009; accepted 16 March 2009; online 19 March 2009)

In the title compound, C₁₅H₁₃ClN₂O₃, the dihedral angle between the two benzene rings is 82.09 (10)° and an intramolecular O—H⋯N hydrogen bond occurs. In the crystal structure, N—H⋯O hydrogen bonds link molecules into chains propagating in [100].

Related literature

For related structures, see: Fun et al. (2008 ); Ali et al. (2007 ); Zhi & Yang (2007 ).

Experimental

Crystal data

C₁₅H₁₃ClN₂O₃
M_r = 304.72
Triclinic, $[P \overline 1]$
a = 5.002 (1) Å
b = 10.866 (2) Å
c = 13.169 (3) Å
α = 83.946 (3)°
β = 81.721 (4)°
γ = 89.540 (3)°
V = 704.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 298 K
0.13 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.964, T_max = 0.972
4214 measured reflections
3017 independent reflections
2342 reflections with I > 2σ(I)
R_int = 0.012

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.117
S = 1.03
3017 reflections
195 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N2	0.82	1.86	2.583 (2)	146
N1—H1⋯O1ⁱ	0.897 (10)	1.976 (14)	2.817 (2)	156 (2)
Symmetry code: (i) x-1, y, z.

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/S1600536809009659/hb2929sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809009659/hb2929Isup2.hkl

checkCIF report

Comment top

Recently, the crystal structures of hydrazone compounds have been widely studied (Fun et al., 2008; Ali et al., 2007; Zhi & Yang, 2007). In this paper, the structure of the title compound, (I), is reported.

In (I), Fig. 1, the dihedral angle between the two benzene rings is 97.9 (2)°. There is an intramolecular O–H···N hydrogen bond (Table 1) in the molecule.

Related literature top

For related structures, see: Fun et al. (2008); Ali et al. (2007); Zhi & Yang (2007).

Experimental top

The compound was prepared by the reaction of equimolar quantities (1.0 mmol each) of 2-hydroxy-4-methoxybenzaldehyde and 2-chlorobenzohydrazide in methanol (100 ml) for 2 h at room temperature. The solution was kept in air for two weeks, forming yellow blocks of (I).

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 (I) showing 30% probability displacement ellipsoids for the non-hydrogen atoms. The H bond is shown as a dashed line.

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

Crystal data top

C₁₅H₁₃ClN₂O₃	Z = 2
M_r = 304.72	F(000) = 316
Triclinic, P1	D_x = 1.437 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.002 (1) Å	Cell parameters from 1381 reflections
b = 10.866 (2) Å	θ = 2.3–26.1°
c = 13.169 (3) Å	µ = 0.28 mm⁻¹
α = 83.946 (3)°	T = 298 K
β = 81.721 (4)°	Block, yellow
γ = 89.540 (3)°	0.13 × 0.12 × 0.10 mm
V = 704.3 (2) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	3017 independent reflections
Radiation source: fine-focus sealed tube	2342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.012
ω scans	θ_max = 27.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
T_min = 0.964, T_max = 0.972	k = −13→13
4214 measured reflections	l = −12→16

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0529P)² + 0.2179P] where P = (F_o² + 2F_c²)/3
3017 reflections	(Δ/σ)_max < 0.001
195 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₁₅H₁₃ClN₂O₃	γ = 89.540 (3)°
M_r = 304.72	V = 704.3 (2) Å³
Triclinic, P1	Z = 2
a = 5.002 (1) Å	Mo Kα radiation
b = 10.866 (2) Å	µ = 0.28 mm⁻¹
c = 13.169 (3) Å	T = 298 K
α = 83.946 (3)°	0.13 × 0.12 × 0.10 mm
β = 81.721 (4)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3017 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2342 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.972	R_int = 0.012
4214 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
3017 reflections	Δρ_min = −0.28 e Å⁻³
195 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	0.46805 (11)	0.16315 (5)	0.36552 (4)	0.05502 (19)
N1	−0.0337 (3)	0.45450 (15)	0.28647 (12)	0.0395 (4)
N2	0.0359 (3)	0.54868 (14)	0.20805 (12)	0.0398 (4)
O1	0.3975 (3)	0.44360 (13)	0.31753 (12)	0.0524 (4)
O2	0.3019 (3)	0.74949 (15)	0.13643 (11)	0.0581 (4)
H2	0.2626	0.6867	0.1759	0.087*
O3	0.1119 (3)	0.94970 (14)	−0.18396 (11)	0.0549 (4)
C1	0.0671 (4)	0.32016 (16)	0.43192 (14)	0.0348 (4)
C2	0.2007 (4)	0.20956 (17)	0.45277 (15)	0.0396 (4)
C3	0.1198 (5)	0.13155 (19)	0.54152 (17)	0.0521 (5)
H3	0.2105	0.0577	0.5543	0.063*
C4	−0.0949 (5)	0.1634 (2)	0.61080 (17)	0.0577 (6)
H4	−0.1477	0.1115	0.6710	0.069*
C5	−0.2326 (4)	0.2716 (2)	0.59178 (16)	0.0527 (5)
H5	−0.3786	0.2925	0.6388	0.063*
C6	−0.1531 (4)	0.34920 (18)	0.50246 (15)	0.0422 (4)
H6	−0.2480	0.4217	0.4894	0.051*
C7	0.1614 (3)	0.41011 (16)	0.34009 (14)	0.0357 (4)
C8	−0.1114 (4)	0.56612 (18)	0.13669 (15)	0.0415 (4)
H8	−0.2606	0.5153	0.1375	0.050*
C9	−0.0462 (4)	0.66529 (17)	0.05418 (14)	0.0383 (4)
C10	0.1562 (4)	0.75315 (18)	0.05729 (14)	0.0400 (4)
C11	0.2109 (4)	0.84952 (19)	−0.02082 (15)	0.0457 (5)
H11	0.3426	0.9082	−0.0171	0.055*
C12	0.0700 (4)	0.85834 (18)	−0.10403 (14)	0.0425 (5)
C13	−0.1288 (4)	0.7717 (2)	−0.10967 (16)	0.0488 (5)
H13	−0.2226	0.7771	−0.1660	0.059*
C14	−0.1851 (4)	0.67777 (19)	−0.03091 (15)	0.0460 (5)
H14	−0.3202	0.6207	−0.0345	0.055*
C15	0.3106 (5)	1.0415 (2)	−0.17935 (18)	0.0566 (6)
H15A	0.2643	1.0815	−0.1176	0.085*
H15B	0.3173	1.1018	−0.2385	0.085*
H15C	0.4840	1.0031	−0.1789	0.085*
H1	−0.205 (3)	0.427 (2)	0.300 (2)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0551 (3)	0.0522 (3)	0.0583 (3)	0.0181 (2)	−0.0093 (2)	−0.0084 (2)
N1	0.0276 (8)	0.0432 (9)	0.0443 (9)	−0.0003 (6)	−0.0041 (7)	0.0097 (7)
N2	0.0331 (8)	0.0414 (9)	0.0420 (9)	0.0022 (6)	−0.0047 (7)	0.0083 (7)
O1	0.0245 (7)	0.0592 (9)	0.0677 (10)	−0.0014 (6)	−0.0054 (6)	0.0187 (7)
O2	0.0571 (9)	0.0685 (10)	0.0483 (9)	−0.0179 (8)	−0.0210 (7)	0.0156 (7)
O3	0.0616 (10)	0.0567 (9)	0.0430 (8)	0.0006 (7)	−0.0085 (7)	0.0118 (7)
C1	0.0308 (9)	0.0364 (9)	0.0379 (9)	−0.0023 (7)	−0.0092 (7)	−0.0006 (7)
C2	0.0392 (10)	0.0385 (10)	0.0429 (10)	0.0018 (8)	−0.0138 (8)	−0.0023 (8)
C3	0.0627 (14)	0.0394 (11)	0.0541 (13)	0.0000 (10)	−0.0184 (11)	0.0092 (9)
C4	0.0657 (15)	0.0581 (14)	0.0451 (12)	−0.0149 (11)	−0.0081 (11)	0.0158 (10)
C5	0.0485 (12)	0.0648 (14)	0.0419 (11)	−0.0100 (11)	0.0010 (9)	−0.0013 (10)
C6	0.0368 (10)	0.0439 (11)	0.0448 (11)	−0.0008 (8)	−0.0050 (8)	−0.0007 (8)
C7	0.0287 (9)	0.0351 (9)	0.0418 (10)	0.0021 (7)	−0.0035 (7)	0.0007 (7)
C8	0.0342 (10)	0.0437 (11)	0.0451 (11)	0.0025 (8)	−0.0052 (8)	0.0011 (8)
C9	0.0340 (9)	0.0414 (10)	0.0384 (10)	0.0079 (8)	−0.0045 (8)	−0.0012 (8)
C10	0.0365 (10)	0.0459 (11)	0.0361 (10)	0.0039 (8)	−0.0053 (8)	0.0022 (8)
C11	0.0427 (11)	0.0481 (11)	0.0438 (11)	−0.0017 (9)	−0.0044 (9)	0.0039 (9)
C12	0.0431 (11)	0.0450 (11)	0.0357 (10)	0.0107 (8)	−0.0002 (8)	0.0045 (8)
C13	0.0531 (13)	0.0533 (12)	0.0415 (11)	0.0070 (10)	−0.0161 (9)	−0.0002 (9)
C14	0.0446 (11)	0.0469 (11)	0.0473 (11)	0.0012 (9)	−0.0122 (9)	−0.0013 (9)
C15	0.0579 (14)	0.0532 (13)	0.0520 (13)	0.0003 (11)	0.0010 (10)	0.0131 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.741 (2)	C5—C6	1.384 (3)
N1—C7	1.343 (2)	C5—H5	0.9300
N1—N2	1.384 (2)	C6—H6	0.9300
N1—H1	0.897 (10)	C8—C9	1.451 (3)
N2—C8	1.273 (2)	C8—H8	0.9300
O1—C7	1.224 (2)	C9—C14	1.395 (3)
O2—C10	1.352 (2)	C9—C10	1.405 (3)
O2—H2	0.8200	C10—C11	1.388 (3)
O3—C12	1.363 (2)	C11—C12	1.381 (3)
O3—C15	1.426 (3)	C11—H11	0.9300
C1—C2	1.392 (3)	C12—C13	1.390 (3)
C1—C6	1.392 (3)	C13—C14	1.376 (3)
C1—C7	1.495 (2)	C13—H13	0.9300
C2—C3	1.382 (3)	C14—H14	0.9300
C3—C4	1.373 (3)	C15—H15A	0.9600
C3—H3	0.9300	C15—H15B	0.9600
C4—C5	1.376 (3)	C15—H15C	0.9600
C4—H4	0.9300

C7—N1—N2	117.48 (14)	N2—C8—C9	119.94 (18)
C7—N1—H1	123.4 (17)	N2—C8—H8	120.0
N2—N1—H1	119.1 (17)	C9—C8—H8	120.0
C8—N2—N1	118.57 (16)	C14—C9—C10	117.45 (18)
C10—O2—H2	109.5	C14—C9—C8	121.07 (18)
C12—O3—C15	117.32 (17)	C10—C9—C8	121.47 (17)
C2—C1—C6	118.04 (17)	O2—C10—C11	117.14 (17)
C2—C1—C7	122.16 (17)	O2—C10—C9	122.07 (17)
C6—C1—C7	119.72 (16)	C11—C10—C9	120.78 (18)
C3—C2—C1	121.08 (19)	C12—C11—C10	120.03 (19)
C3—C2—Cl1	118.05 (16)	C12—C11—H11	120.0
C1—C2—Cl1	120.83 (15)	C10—C11—H11	120.0
C4—C3—C2	119.7 (2)	O3—C12—C11	123.68 (19)
C4—C3—H3	120.1	O3—C12—C13	115.99 (18)
C2—C3—H3	120.1	C11—C12—C13	120.33 (18)
C3—C4—C5	120.49 (19)	C14—C13—C12	119.22 (18)
C3—C4—H4	119.8	C14—C13—H13	120.4
C5—C4—H4	119.8	C12—C13—H13	120.4
C4—C5—C6	119.8 (2)	C13—C14—C9	122.17 (19)
C4—C5—H5	120.1	C13—C14—H14	118.9
C6—C5—H5	120.1	C9—C14—H14	118.9
C5—C6—C1	120.87 (19)	O3—C15—H15A	109.5
C5—C6—H6	119.6	O3—C15—H15B	109.5
C1—C6—H6	119.6	H15A—C15—H15B	109.5
O1—C7—N1	122.63 (16)	O3—C15—H15C	109.5
O1—C7—C1	122.38 (16)	H15A—C15—H15C	109.5
N1—C7—C1	114.96 (15)	H15B—C15—H15C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N2	0.82	1.86	2.583 (2)	146
N1—H1···O1ⁱ	0.90 (1)	1.98 (1)	2.817 (2)	156 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃ClN₂O₃
M_r	304.72
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.002 (1), 10.866 (2), 13.169 (3)
α, β, γ (°)	83.946 (3), 81.721 (4), 89.540 (3)
V (Å³)	704.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.13 × 0.12 × 0.10

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.964, 0.972
No. of measured, independent and observed [I > 2σ(I)] reflections	4214, 3017, 2342
R_int	0.012
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.117, 1.03
No. of reflections	3017
No. of parameters	195
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)	0.19, −0.28

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
O2—H2···N2	0.82	1.86	2.583 (2)	146
N1—H1···O1ⁱ	0.897 (10)	1.976 (14)	2.817 (2)	156 (2)

Symmetry code: (i) x−1, y, z.

References

Ali, H. M., Zuraini, K., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1729–o1730. 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
Fun, H.-K., Jebas, S. R., Sujith, K. V., Patil, P. S. & Kalluraya, B. (2008). Acta Cryst. E64, o1907–o1908. 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
Zhi, F. & Yang, Y.-L. (2007). Acta Cryst. E63, o4471. Web of Science CSD CrossRef IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o808

doi:10.1107/S1600536809009659

Open

access