3-Chloro-N′-[(2-meth­oxy­naphthalen-1-yl)methyl­idene]benzohydrazide

Li, T.-Y.; Ge, Y.-X.

doi:10.1107/S1600536811000924

organic compounds

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Volume 67| Part 2| February 2011| Page o374

doi:10.1107/S1600536811000924

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3-Chloro-N′-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide

Tian-Yi Li ^a ^* and Yan-Xia Ge ^a

^aSchool of Chemical Engineering, Changchun University of Technology, Changchun 130012, People's Republic of China
^*Correspondence e-mail: cooperationwell@126.com

(Received 31 December 2010; accepted 6 January 2011; online 12 January 2011)

The title compound, C₁₉H₁₅ClN₂O₂, was prepared by the reaction of 2-methoxy-1-naphthaldehyde with 3-chlorobenzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 69.0 (3)°. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into chains along the c axis. The crystal packing exhibits π–π interactions, as indicated by distances of 3.768 (3) Å between the centroids of the naphthyl rings of neighbouring molecules.

Related literature

For a related structure, see: Li & Li (2011). For reference bond lengths, see: Allen et al. (1987 ). For details of the synthesis, see: Zhu (2010 ).

Experimental

Crystal data

C₁₉H₁₅ClN₂O₂
M_r = 338.78
Monoclinic, P 2₁ /c
a = 12.181 (2) Å
b = 16.953 (4) Å
c = 8.5482 (15) Å
β = 109.446 (2)°
V = 1664.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 298 K
0.18 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.958, T_max = 0.962
8964 measured reflections
3586 independent reflections
1624 reflections with I > 2σ(I)
R_int = 0.067

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.147
S = 1.00
3586 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O2ⁱ	0.91 (3)	2.04 (3)	2.937 (3)	170 (3)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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/S1600536811000924/cv5034sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811000924/cv5034Isup2.hkl

checkCIF report

Comment top

In continuation of our structural study of naphthylidenebenzohydrazide derivatives (Li & Li, 2011) we present here the title compound (I).

In (I) (Fig. 1),the dihedral angle between the benzene ring and the naphthyl bicycle is 69.0 (3)°. All the bond lengths are within normal values (Allen et al., 1987). Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains along the c axis (Fig. 2). The crystal packing exhibits π-π interactions proved by short distances of 3.768 (3) Å between the centroids of naphthyl rings from the neighbouring molecules.

Related literature top

For a structure, see: Li & Li (2011). For reference bond lengths, see: Allen et al. (1987). For details of the synthesis, see: Zhu (2010).

Experimental top

The compound was prepared and crystallized according to the literature method (Zhu, 2010). 2-Methoxy-1-naphthaldehyde (0.186 g, 1 mmol) and 3-chlorobenzohydrazide (0.171 g, 1 mmol) were dissolved in 30 ml absolute methanol. The mixture was stirred at reflux for 10 min, and cooled to room temperature. The clear colorless solution was left to slow evaporation in air for eight days, yielding colorless block-shaped crystals, which were collected by filtration and washed with methanol.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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 compound with 30% probability displacement ellipsoids for non-hydrogen atoms.
	Fig. 2. A portion of the crystal packing showing hydrogen bonds as dashed lines.

3-Chloro-N'-[(2-methoxynaphthalen-1-yl)methylidene]benzohydrazide top

Crystal data top

C₁₉H₁₅ClN₂O₂	F(000) = 704
M_r = 338.78	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.181 (2) Å	Cell parameters from 762 reflections
b = 16.953 (4) Å	θ = 2.5–24.3°
c = 8.5482 (15) Å	µ = 0.24 mm⁻¹
β = 109.446 (2)°	T = 298 K
V = 1664.5 (6) Å³	Block, colourless
Z = 4	0.18 × 0.18 × 0.16 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	3586 independent reflections
Radiation source: fine-focus sealed tube	1624 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→15
T_min = 0.958, T_max = 0.962	k = −19→21
8964 measured reflections	l = −10→10

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0386P)²] where P = (F_o² + 2F_c²)/3
3586 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.19 e Å⁻³
1 restraint	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₉H₁₅ClN₂O₂	V = 1664.5 (6) Å³
M_r = 338.78	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.181 (2) Å	µ = 0.24 mm⁻¹
b = 16.953 (4) Å	T = 298 K
c = 8.5482 (15) Å	0.18 × 0.18 × 0.16 mm
β = 109.446 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3586 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1624 reflections with I > 2σ(I)
T_min = 0.958, T_max = 0.962	R_int = 0.067
8964 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	1 restraint
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.19 e Å⁻³
3586 reflections	Δρ_min = −0.24 e Å⁻³
221 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	0.57105 (8)	0.10288 (6)	1.03193 (12)	0.0793 (4)
N1	0.8646 (2)	0.28050 (15)	0.6055 (3)	0.0469 (7)
N2	0.7753 (2)	0.24546 (15)	0.6487 (3)	0.0467 (7)
O1	0.9252 (2)	0.49223 (13)	0.7763 (3)	0.0709 (7)
O2	0.71701 (19)	0.17210 (12)	0.4129 (3)	0.0619 (7)
C1	1.0045 (3)	0.38640 (17)	0.6734 (4)	0.0453 (8)
C2	1.0122 (3)	0.46507 (19)	0.7236 (4)	0.0540 (9)
C3	1.1046 (3)	0.5131 (2)	0.7182 (4)	0.0707 (11)
H3	1.1088	0.5653	0.7527	0.085*
C4	1.1874 (3)	0.4831 (2)	0.6626 (5)	0.0753 (11)
H4	1.2479	0.5157	0.6589	0.090*
C5	1.1857 (3)	0.4049 (2)	0.6107 (4)	0.0563 (9)
C6	1.2739 (3)	0.3739 (2)	0.5573 (5)	0.0737 (11)
H6	1.3347	0.4067	0.5556	0.088*
C7	1.2739 (3)	0.2977 (3)	0.5082 (5)	0.0751 (11)
H7	1.3337	0.2785	0.4739	0.090*
C8	1.1819 (3)	0.2489 (2)	0.5103 (4)	0.0676 (10)
H8	1.1807	0.1965	0.4773	0.081*
C9	1.0942 (3)	0.27685 (19)	0.5598 (4)	0.0549 (9)
H9	1.0337	0.2431	0.5582	0.066*
C10	1.0917 (3)	0.35562 (17)	0.6136 (4)	0.0458 (8)
C11	0.9075 (3)	0.34138 (18)	0.6916 (4)	0.0488 (8)
H11	0.8752	0.3580	0.7703	0.059*
C12	0.7072 (3)	0.19108 (18)	0.5452 (4)	0.0463 (8)
C13	0.6157 (3)	0.15628 (16)	0.6049 (4)	0.0418 (7)
C14	0.6300 (2)	0.14888 (16)	0.7713 (4)	0.0433 (8)
H14	0.6972	0.1682	0.8504	0.052*
C15	0.5463 (3)	0.11327 (18)	0.8211 (4)	0.0506 (8)
C16	0.4458 (3)	0.0859 (2)	0.7070 (5)	0.0752 (11)
H16	0.3886	0.0626	0.7417	0.090*
C17	0.4298 (3)	0.0930 (2)	0.5414 (5)	0.0840 (12)
H17	0.3618	0.0743	0.4633	0.101*
C18	0.5144 (3)	0.1278 (2)	0.4901 (4)	0.0670 (10)
H18	0.5031	0.1322	0.3774	0.080*
C19	0.9307 (4)	0.5719 (2)	0.8359 (5)	0.0905 (13)
H19A	1.0029	0.5798	0.9245	0.136*
H19B	0.8669	0.5812	0.8758	0.136*
H19C	0.9260	0.6079	0.7471	0.136*
H2	0.757 (3)	0.265 (2)	0.736 (3)	0.109*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0826 (7)	0.1061 (8)	0.0635 (7)	−0.0240 (6)	0.0433 (6)	0.0039 (5)
N1	0.0513 (16)	0.0548 (16)	0.0406 (16)	−0.0094 (13)	0.0231 (14)	−0.0007 (13)
N2	0.0505 (16)	0.0514 (16)	0.0461 (18)	−0.0066 (13)	0.0267 (15)	−0.0026 (13)
O1	0.0942 (18)	0.0526 (15)	0.0704 (18)	0.0061 (13)	0.0333 (16)	−0.0040 (12)
O2	0.0833 (17)	0.0664 (15)	0.0490 (15)	−0.0153 (12)	0.0392 (14)	−0.0103 (11)
C1	0.055 (2)	0.0434 (19)	0.0354 (19)	−0.0063 (15)	0.0130 (17)	0.0031 (14)
C2	0.066 (2)	0.050 (2)	0.041 (2)	−0.0017 (18)	0.0120 (18)	0.0071 (16)
C3	0.087 (3)	0.047 (2)	0.067 (3)	−0.015 (2)	0.010 (2)	−0.0055 (18)
C4	0.070 (3)	0.067 (3)	0.081 (3)	−0.030 (2)	0.015 (2)	0.002 (2)
C5	0.054 (2)	0.065 (2)	0.047 (2)	−0.0132 (17)	0.0121 (18)	0.0083 (18)
C6	0.055 (2)	0.091 (3)	0.080 (3)	−0.014 (2)	0.029 (2)	0.008 (2)
C7	0.056 (2)	0.094 (3)	0.085 (3)	0.004 (2)	0.037 (2)	0.006 (2)
C8	0.068 (2)	0.075 (2)	0.068 (3)	−0.001 (2)	0.034 (2)	−0.001 (2)
C9	0.051 (2)	0.064 (2)	0.054 (2)	−0.0092 (17)	0.0235 (19)	0.0010 (17)
C10	0.053 (2)	0.0466 (19)	0.0367 (19)	−0.0077 (15)	0.0138 (17)	0.0048 (15)
C11	0.052 (2)	0.055 (2)	0.042 (2)	−0.0037 (16)	0.0195 (17)	0.0020 (17)
C12	0.053 (2)	0.0482 (19)	0.044 (2)	0.0026 (16)	0.0239 (18)	0.0015 (16)
C13	0.0424 (19)	0.0426 (17)	0.042 (2)	0.0016 (14)	0.0169 (17)	−0.0018 (15)
C14	0.0440 (18)	0.0436 (17)	0.047 (2)	−0.0031 (14)	0.0221 (17)	−0.0027 (15)
C15	0.048 (2)	0.058 (2)	0.055 (2)	−0.0020 (16)	0.0298 (19)	0.0024 (17)
C16	0.049 (2)	0.098 (3)	0.086 (3)	−0.019 (2)	0.032 (2)	0.003 (2)
C17	0.055 (2)	0.126 (4)	0.065 (3)	−0.029 (2)	0.012 (2)	−0.007 (3)
C18	0.064 (2)	0.087 (3)	0.049 (2)	−0.010 (2)	0.018 (2)	0.0005 (19)
C19	0.141 (4)	0.059 (2)	0.065 (3)	0.024 (2)	0.025 (3)	−0.007 (2)

Geometric parameters (Å, º) top

Cl1—C15	1.735 (3)	C7—H7	0.9300
N1—C11	1.274 (3)	C8—C9	1.358 (4)
N1—N2	1.392 (3)	C8—H8	0.9300
N2—C12	1.354 (4)	C9—C10	1.416 (4)
N2—H2	0.91 (3)	C9—H9	0.9300
O1—C2	1.362 (4)	C11—H11	0.9300
O1—C19	1.437 (4)	C12—C13	1.494 (4)
O2—C12	1.219 (3)	C13—C14	1.380 (4)
C1—C2	1.394 (4)	C13—C18	1.383 (4)
C1—C10	1.422 (4)	C14—C15	1.370 (4)
C1—C11	1.458 (4)	C14—H14	0.9300
C2—C3	1.402 (4)	C15—C16	1.367 (4)
C3—C4	1.349 (4)	C16—C17	1.368 (5)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.395 (5)	C17—C18	1.379 (5)
C4—H4	0.9300	C17—H17	0.9300
C5—C6	1.402 (5)	C18—H18	0.9300
C5—C10	1.425 (4)	C19—H19A	0.9600
C6—C7	1.358 (5)	C19—H19B	0.9600
C6—H6	0.9300	C19—H19C	0.9600
C7—C8	1.399 (5)

C11—N1—N2	113.5 (2)	C9—C10—C5	116.3 (3)
C12—N2—N1	118.7 (2)	C1—C10—C5	119.5 (3)
C12—N2—H2	121 (2)	N1—C11—C1	123.7 (3)
N1—N2—H2	119 (2)	N1—C11—H11	118.2
C2—O1—C19	119.1 (3)	C1—C11—H11	118.2
C2—C1—C10	118.7 (3)	O2—C12—N2	123.9 (3)
C2—C1—C11	116.2 (3)	O2—C12—C13	121.8 (3)
C10—C1—C11	125.1 (3)	N2—C12—C13	114.2 (3)
O1—C2—C1	116.4 (3)	C14—C13—C18	118.5 (3)
O1—C2—C3	122.4 (3)	C14—C13—C12	122.4 (3)
C1—C2—C3	121.1 (3)	C18—C13—C12	119.1 (3)
C4—C3—C2	119.7 (3)	C15—C14—C13	120.6 (3)
C4—C3—H3	120.1	C15—C14—H14	119.7
C2—C3—H3	120.1	C13—C14—H14	119.7
C3—C4—C5	122.4 (3)	C16—C15—C14	120.7 (3)
C3—C4—H4	118.8	C16—C15—Cl1	120.8 (2)
C5—C4—H4	118.8	C14—C15—Cl1	118.5 (3)
C4—C5—C6	121.9 (3)	C15—C16—C17	119.5 (3)
C4—C5—C10	118.6 (3)	C15—C16—H16	120.2
C6—C5—C10	119.5 (3)	C17—C16—H16	120.2
C7—C6—C5	122.4 (3)	C16—C17—C18	120.2 (3)
C7—C6—H6	118.8	C16—C17—H17	119.9
C5—C6—H6	118.8	C18—C17—H17	119.9
C6—C7—C8	118.4 (3)	C17—C18—C13	120.5 (3)
C6—C7—H7	120.8	C17—C18—H18	119.7
C8—C7—H7	120.8	C13—C18—H18	119.7
C9—C8—C7	121.0 (3)	O1—C19—H19A	109.5
C9—C8—H8	119.5	O1—C19—H19B	109.5
C7—C8—H8	119.5	H19A—C19—H19B	109.5
C8—C9—C10	122.3 (3)	O1—C19—H19C	109.5
C8—C9—H9	118.9	H19A—C19—H19C	109.5
C10—C9—H9	118.9	H19B—C19—H19C	109.5
C9—C10—C1	124.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.91 (3)	2.04 (3)	2.937 (3)	170 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₁₅ClN₂O₂
M_r	338.78
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	12.181 (2), 16.953 (4), 8.5482 (15)
β (°)	109.446 (2)
V (Å³)	1664.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.18 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	8964, 3586, 1624
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.147, 1.00
No. of reflections	3586
No. of parameters	221
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, −0.24

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O2ⁱ	0.91 (3)	2.04 (3)	2.937 (3)	170 (3)

Symmetry code: (i) x, −y+1/2, z+1/2.

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. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Li, T.-Y. & Li, W. (2011). Acta Cryst. E67, o373. 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
Zhu, H.-Y. (2010). Acta Cryst. E66, o2562. Web of Science CSD CrossRef IUCr Journals Google Scholar

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doi:10.1107/S1600536811000924

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