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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

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 ππ 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)[Li, T.-Y. & Li, W. (2011). Acta Cryst. E67, o373.]. For reference bond lengths, see: Allen et al. (1987[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.]). For details of the synthesis, see: Zhu (2010[Zhu, H.-Y. (2010). Acta Cryst. E66, o2562.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15ClN2O2

  • Mr = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.962

  • 8964 measured reflections

  • 3586 independent reflections

  • 1624 reflections with I > 2σ(I)

  • Rint = 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

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.24 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


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.

Refinement top

The amino H atom was located from a difference Fourier map and refined isotropically, with the N—H distance restrained to 0.90 (1) Å. The other H atoms were positioned geometrically and refined using the riding-model approximation, with C—H = 0.93–0.96 Å, and Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C19).

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
[Figure 1] Fig. 1. The molecular structure of the title compound with 30% probability displacement ellipsoids for non-hydrogen atoms.
[Figure 2] 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
C19H15ClN2O2F(000) = 704
Mr = 338.78Dx = 1.352 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.181 (2) ÅCell parameters from 762 reflections
b = 16.953 (4) Åθ = 2.5–24.3°
c = 8.5482 (15) ŵ = 0.24 mm1
β = 109.446 (2)°T = 298 K
V = 1664.5 (6) Å3Block, colourless
Z = 40.18 × 0.18 × 0.16 mm
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3586 independent reflections
Radiation source: fine-focus sealed tube1624 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.067
ω scansθmax = 27.0°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
h = 1415
Tmin = 0.958, Tmax = 0.962k = 1921
8964 measured reflectionsl = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.060Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H 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 parametersΔρmax = 0.19 e Å3
1 restraintΔρmin = 0.24 e Å3
Crystal data top
C19H15ClN2O2V = 1664.5 (6) Å3
Mr = 338.78Z = 4
Monoclinic, P21/cMo Kα radiation
a = 12.181 (2) ŵ = 0.24 mm1
b = 16.953 (4) ÅT = 298 K
c = 8.5482 (15) Å0.18 × 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)
Tmin = 0.958, Tmax = 0.962Rint = 0.067
8964 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0601 restraint
wR(F2) = 0.147H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.19 e Å3
3586 reflectionsΔρmin = 0.24 e Å3
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
xyzUiso*/Ueq
Cl10.57105 (8)0.10288 (6)1.03193 (12)0.0793 (4)
N10.8646 (2)0.28050 (15)0.6055 (3)0.0469 (7)
N20.7753 (2)0.24546 (15)0.6487 (3)0.0467 (7)
O10.9252 (2)0.49223 (13)0.7763 (3)0.0709 (7)
O20.71701 (19)0.17210 (12)0.4129 (3)0.0619 (7)
C11.0045 (3)0.38640 (17)0.6734 (4)0.0453 (8)
C21.0122 (3)0.46507 (19)0.7236 (4)0.0540 (9)
C31.1046 (3)0.5131 (2)0.7182 (4)0.0707 (11)
H31.10880.56530.75270.085*
C41.1874 (3)0.4831 (2)0.6626 (5)0.0753 (11)
H41.24790.51570.65890.090*
C51.1857 (3)0.4049 (2)0.6107 (4)0.0563 (9)
C61.2739 (3)0.3739 (2)0.5573 (5)0.0737 (11)
H61.33470.40670.55560.088*
C71.2739 (3)0.2977 (3)0.5082 (5)0.0751 (11)
H71.33370.27850.47390.090*
C81.1819 (3)0.2489 (2)0.5103 (4)0.0676 (10)
H81.18070.19650.47730.081*
C91.0942 (3)0.27685 (19)0.5598 (4)0.0549 (9)
H91.03370.24310.55820.066*
C101.0917 (3)0.35562 (17)0.6136 (4)0.0458 (8)
C110.9075 (3)0.34138 (18)0.6916 (4)0.0488 (8)
H110.87520.35800.77030.059*
C120.7072 (3)0.19108 (18)0.5452 (4)0.0463 (8)
C130.6157 (3)0.15628 (16)0.6049 (4)0.0418 (7)
C140.6300 (2)0.14888 (16)0.7713 (4)0.0433 (8)
H140.69720.16820.85040.052*
C150.5463 (3)0.11327 (18)0.8211 (4)0.0506 (8)
C160.4458 (3)0.0859 (2)0.7070 (5)0.0752 (11)
H160.38860.06260.74170.090*
C170.4298 (3)0.0930 (2)0.5414 (5)0.0840 (12)
H170.36180.07430.46330.101*
C180.5144 (3)0.1278 (2)0.4901 (4)0.0670 (10)
H180.50310.13220.37740.080*
C190.9307 (4)0.5719 (2)0.8359 (5)0.0905 (13)
H19A1.00290.57980.92450.136*
H19B0.86690.58120.87580.136*
H19C0.92600.60790.74710.136*
H20.757 (3)0.265 (2)0.736 (3)0.109*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0826 (7)0.1061 (8)0.0635 (7)0.0240 (6)0.0433 (6)0.0039 (5)
N10.0513 (16)0.0548 (16)0.0406 (16)0.0094 (13)0.0231 (14)0.0007 (13)
N20.0505 (16)0.0514 (16)0.0461 (18)0.0066 (13)0.0267 (15)0.0026 (13)
O10.0942 (18)0.0526 (15)0.0704 (18)0.0061 (13)0.0333 (16)0.0040 (12)
O20.0833 (17)0.0664 (15)0.0490 (15)0.0153 (12)0.0392 (14)0.0103 (11)
C10.055 (2)0.0434 (19)0.0354 (19)0.0063 (15)0.0130 (17)0.0031 (14)
C20.066 (2)0.050 (2)0.041 (2)0.0017 (18)0.0120 (18)0.0071 (16)
C30.087 (3)0.047 (2)0.067 (3)0.015 (2)0.010 (2)0.0055 (18)
C40.070 (3)0.067 (3)0.081 (3)0.030 (2)0.015 (2)0.002 (2)
C50.054 (2)0.065 (2)0.047 (2)0.0132 (17)0.0121 (18)0.0083 (18)
C60.055 (2)0.091 (3)0.080 (3)0.014 (2)0.029 (2)0.008 (2)
C70.056 (2)0.094 (3)0.085 (3)0.004 (2)0.037 (2)0.006 (2)
C80.068 (2)0.075 (2)0.068 (3)0.001 (2)0.034 (2)0.001 (2)
C90.051 (2)0.064 (2)0.054 (2)0.0092 (17)0.0235 (19)0.0010 (17)
C100.053 (2)0.0466 (19)0.0367 (19)0.0077 (15)0.0138 (17)0.0048 (15)
C110.052 (2)0.055 (2)0.042 (2)0.0037 (16)0.0195 (17)0.0020 (17)
C120.053 (2)0.0482 (19)0.044 (2)0.0026 (16)0.0239 (18)0.0015 (16)
C130.0424 (19)0.0426 (17)0.042 (2)0.0016 (14)0.0169 (17)0.0018 (15)
C140.0440 (18)0.0436 (17)0.047 (2)0.0031 (14)0.0221 (17)0.0027 (15)
C150.048 (2)0.058 (2)0.055 (2)0.0020 (16)0.0298 (19)0.0024 (17)
C160.049 (2)0.098 (3)0.086 (3)0.019 (2)0.032 (2)0.003 (2)
C170.055 (2)0.126 (4)0.065 (3)0.029 (2)0.012 (2)0.007 (3)
C180.064 (2)0.087 (3)0.049 (2)0.010 (2)0.018 (2)0.0005 (19)
C190.141 (4)0.059 (2)0.065 (3)0.024 (2)0.025 (3)0.007 (2)
Geometric parameters (Å, º) top
Cl1—C151.735 (3)C7—H70.9300
N1—C111.274 (3)C8—C91.358 (4)
N1—N21.392 (3)C8—H80.9300
N2—C121.354 (4)C9—C101.416 (4)
N2—H20.91 (3)C9—H90.9300
O1—C21.362 (4)C11—H110.9300
O1—C191.437 (4)C12—C131.494 (4)
O2—C121.219 (3)C13—C141.380 (4)
C1—C21.394 (4)C13—C181.383 (4)
C1—C101.422 (4)C14—C151.370 (4)
C1—C111.458 (4)C14—H140.9300
C2—C31.402 (4)C15—C161.367 (4)
C3—C41.349 (4)C16—C171.368 (5)
C3—H30.9300C16—H160.9300
C4—C51.395 (5)C17—C181.379 (5)
C4—H40.9300C17—H170.9300
C5—C61.402 (5)C18—H180.9300
C5—C101.425 (4)C19—H19A0.9600
C6—C71.358 (5)C19—H19B0.9600
C6—H60.9300C19—H19C0.9600
C7—C81.399 (5)
C11—N1—N2113.5 (2)C9—C10—C5116.3 (3)
C12—N2—N1118.7 (2)C1—C10—C5119.5 (3)
C12—N2—H2121 (2)N1—C11—C1123.7 (3)
N1—N2—H2119 (2)N1—C11—H11118.2
C2—O1—C19119.1 (3)C1—C11—H11118.2
C2—C1—C10118.7 (3)O2—C12—N2123.9 (3)
C2—C1—C11116.2 (3)O2—C12—C13121.8 (3)
C10—C1—C11125.1 (3)N2—C12—C13114.2 (3)
O1—C2—C1116.4 (3)C14—C13—C18118.5 (3)
O1—C2—C3122.4 (3)C14—C13—C12122.4 (3)
C1—C2—C3121.1 (3)C18—C13—C12119.1 (3)
C4—C3—C2119.7 (3)C15—C14—C13120.6 (3)
C4—C3—H3120.1C15—C14—H14119.7
C2—C3—H3120.1C13—C14—H14119.7
C3—C4—C5122.4 (3)C16—C15—C14120.7 (3)
C3—C4—H4118.8C16—C15—Cl1120.8 (2)
C5—C4—H4118.8C14—C15—Cl1118.5 (3)
C4—C5—C6121.9 (3)C15—C16—C17119.5 (3)
C4—C5—C10118.6 (3)C15—C16—H16120.2
C6—C5—C10119.5 (3)C17—C16—H16120.2
C7—C6—C5122.4 (3)C16—C17—C18120.2 (3)
C7—C6—H6118.8C16—C17—H17119.9
C5—C6—H6118.8C18—C17—H17119.9
C6—C7—C8118.4 (3)C17—C18—C13120.5 (3)
C6—C7—H7120.8C17—C18—H18119.7
C8—C7—H7120.8C13—C18—H18119.7
C9—C8—C7121.0 (3)O1—C19—H19A109.5
C9—C8—H8119.5O1—C19—H19B109.5
C7—C8—H8119.5H19A—C19—H19B109.5
C8—C9—C10122.3 (3)O1—C19—H19C109.5
C8—C9—H9118.9H19A—C19—H19C109.5
C10—C9—H9118.9H19B—C19—H19C109.5
C9—C10—C1124.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.91 (3)2.04 (3)2.937 (3)170 (3)
Symmetry code: (i) x, y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formulaC19H15ClN2O2
Mr338.78
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)12.181 (2), 16.953 (4), 8.5482 (15)
β (°) 109.446 (2)
V3)1664.5 (6)
Z4
Radiation typeMo Kα
µ (mm1)0.24
Crystal size (mm)0.18 × 0.18 × 0.16
Data collection
DiffractometerBruker APEXII CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.958, 0.962
No. of measured, independent and
observed [I > 2σ(I)] reflections
8964, 3586, 1624
Rint0.067
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.060, 0.147, 1.00
No. of reflections3586
No. of parameters221
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.19, 0.24

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O2i0.91 (3)2.04 (3)2.937 (3)170 (3)
Symmetry code: (i) x, y+1/2, z+1/2.
 

References

First citationAllen, 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
First citationBruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, T.-Y. & Li, W. (2011). Acta Cryst. E67, o373.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationZhu, H.-Y. (2010). Acta Cryst. E66, o2562.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds