3-Chloro-N'-[(2-meth-oxy-naphthalen-1-yl)methyl-idene]benzohydrazide.

The title compound, C(19)H(15)ClN(2)O(2), was prepared by the reaction of 2-meth-oxy-1-naphthaldehyde with 3-chloro-benzohydrazide in methanol. The dihedral angle between the benzene ring and the naphthyl ring system is 69.0 (3)°. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the c axis. The crystal packing exhibits π-π inter-actions, as indicated by distances of 3.768 (3) Å between the centroids of the naphthyl rings of neighbouring mol-ecules.

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 = 338.78

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.147

S = 1.00

3586 reflections

221 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.24 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000924/cv5034sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H15ClN2O2	F(000) = 704
Mr = 338.78	Dx = 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

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

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(Fo2) + (0.0386P)2] where P = (Fo2 + 2Fc2)/3
3586 reflections	(Δ/σ)max < 0.001
221 parameters	Δρmax = 0.19 e Å−3
1 restraint	Δρmin = −0.24 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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)

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) .