Crystal structure of N-[(E)-(1,3-benzodioxol-5-yl)­methyl­idene]-4-chloro­aniline

García-Merinos, J.P.; López, Y.; González-Campos, J.B.; Aviña-Verduzco, J.A.; Río, R.E. del; Santillan, R.

doi:10.1107/S1600536814022892

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1195-o1196

doi:10.1107/S1600536814022892

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Crystal structure of N-[(E)-(1,3-benzodioxol-5-yl)methylidene]-4-chloroaniline

J. Pablo García-Merinos,^a Yliana López,^a ^* J. Betzabe González-Campos,^a Judit A. Aviña-Verduzco,^a Rosa E. del Río ^a and Rosa Santillan ^b

^aInstituto de Investigaciones Químico-Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Morelia, Michoacán, CP 58000, México, and ^bDepartamento de Química, CINVESTAV-IPN, Apdo. Postal 14-740, 07000 México, D.F., México
^*Correspondence e-mail: ylopez@umich.mx

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 15 October 2014; accepted 18 October 2014; online 24 October 2014)

In the title compound, C₁₄H₁₀ClNO₂, obtained by the condensation of 4-chloroaniline and piperonal, the five-membered ring is almost planar (r.m.s. deviation = 0.023 Å) and the dihedral angle between the aromatic rings is 43.22 (14)°. In the crystal, a short O⋯Cl contact of 3.173 (2) Å is observed. The molecules are arranged into corrugated (010) layers.

Keywords: crystal structure; O⋯Cl contact; Schiff base.

CCDC reference: 1029773

1. Related literature

Schiff bases have applications in fields, such as organic synthesis (Meyer et al., 2007 ), catalysis (Itsuno et al., 1990 ), materials science (Sliwa et al., 2008 ), supramolecular (Sreenivasulu et al., 2012 ) and coordination chemistry (Drozdzak et al., 2005 ; MacLachlan et al., 1996 ). They display a broad spectrum of biological (Garavelli et al., 1997 ; Ren et al., 2002 ) and pharmacological properties, such as antibacterial, analgesic, antipyretic, anti-inflammatory and anticancer activities and can act as plant-growth regulators (Prakash et al., 2011 and Gaur 2003 ). For related structures, see: Tahir et al. (2010a ,b ). For further synthetic details, see: Rodríguez et al. (2007 ); Domínguez et al. (2011 ).

2. Experimental

2.1. Crystal data

C₁₄H₁₀ClNO₂
M_r = 259.69
Orthorhombic, P c a b
a = 6.0014 (4) Å
b = 13.9015 (16) Å
c = 28.867 (3) Å
V = 2408.3 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 K
0.19 × 0.10 × 0.08 mm

2.2. Data collection

Nonius KappaCCD diffractometer
5318 measured reflections
2377 independent reflections
882 reflections with I > 2σ(I)
R_int = 0.079

2.3. Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.121
S = 0.88
2377 reflections
203 parameters
All H-atom parameters refined
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Data collection: COLLECT (Nonius, 1999 ); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997 ); data reduction: HKL DENZO (Otwinowski & Minor 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Supporting information

CCDC reference: 1029773

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814022892/hb7302sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814022892/hb7302Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814022892/hb7302Isup3.cml

checkCIF report

Comment top

Schiff bases are some of the most widely used organic compounds. They are important due to successful applications in several fields, such as organic synthesis (Meyer et al., 2007), catalysis (Itsuno et al., 1990) and materials science (Sliwa, et al., 2008), supramolecular chemistry (Sreenivasulu et al., 2012), coordination chemistry (Drozdzak et al., 2005 and MacLachlan et al., 1996), as well as for the broad spectrum of biological (Garavelli et al., 1997 and Ren et al., 2002) and pharmacological properties, such as antibacterial, analgesic, antipyretic, anti-inflammatory, anticancer, and as plant growth regulators (Prakash et al., 2011 and Gaur 2003).

In previous studies, we have described an X-ray diffraction and spectroscopic study of the ketoenol tautomeric forms of six enaminones prepared from salicylaldehyde and substituted anilines (Rodríguez et al., 2007). In addition we have reported a spectroscopic study of several ortho-hydroxy Schiff bases; the corresponding crystal structures were analyzed to identify their characteristic hydrogen bonding patterns, which was necessary in order to have evidence about the influence (electronic and/or structural) of the substituents on the tautomeric structure from a crystallographic perspective (Domínguez et al., 2011). To continue our studies on Schiff base ligands, we synthesized the title compound (I) obtained by condensation of 4-chloroaniline and piperonal.

The dihedral angle between the two aromatic rings is 43.22 (14)° and the C1—N1—C7—C8 torsion angle is -179.0 (3)° (Table 1). The C4—Cl1 and C7=N1 bond distances are 1.716 (4) Å and 1.260 (4) Å, respectively (Table 1). These values are slightly shorter than the average values reported for Car—Cl C8=N1, 1.283 (5) Å (Tahir et al., 2010a) and for C8=N1, 1.271 (2) Å in related Schiff bases containing the piperonal fragment (Tahir et al., 2010b).

Related literature top

Schiff bases have applications in fields, such as organic synthesis (Meyer et al., 2007), catalysis (Itsuno et al., 1990), materials science (Sliwa et al., 2008), supramolecular (Sreenivasulu et al., 2012) and coordination chemistry (Drozdzak et al., 2005; MacLachlan et al., 1996). They display a broad spectrum of biological (Garavelli et al., 1997; Ren et al., 2002) and pharmacological properties, such as antibacterial, analgesic, antipyretic, anti-inflammatory and anticancer activities and can act as plant-growth regulators (Prakash et al., 2011 and Gaur 2003). For related structures, see: Tahir et al. (2010a,b). For further synthetic details, see: Rodríguez et al. (2007); Domínguez et al. (2011).

Experimental top

A solution of 4-chloroaniline (0.500 g, 3.9 mmol) and piperonal (0.260 g, 3.01 mmol) in methanol (55 mL) was heated under reflux for 3h, with a Dean-Stark apparatus used for the azeotropic removal of water and allowed to cool to room temperature. Removal of solvent affords compound I as a pale yellow solid which was washed with hexane to obtain the product in 36% yield (m.p. 347-349 K). Colourless blocks were grown by slow evaporation from a solvent mixture of methanol:ethyl acetate (1:1). Spectroscopic data for the title compound are given in the archived CIF.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: HKL SCALEPACK (Otwinowski & Minor 1997); data reduction: HKL DENZO and SCALEPACK (Otwinowski & Minor 1997); program(s) used to solve structure: SHELXS97 (Sheldrick 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).

Figures top

View of (I), with displacement ellipsoids drawn at 30% probability level.

N-[(E)-(1,3-Benzodioxol-5-yl)methylidene]-4-chloroaniline top

Crystal data top

C₁₄H₁₀ClNO₂	D_x = 1.432 Mg m⁻³
M_r = 259.69	Melting point: 347(2) K
Orthorhombic, Pcab	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2bc 2ac	Cell parameters from 600 reflections
a = 6.0014 (4) Å	θ = 2.9–27.7°
b = 13.9015 (16) Å	µ = 0.31 mm⁻¹
c = 28.867 (3) Å	T = 293 K
V = 2408.3 (4) Å³	Block, colourless
Z = 8	0.19 × 0.10 × 0.08 mm
F(000) = 1072

Data collection top

Nonius KappaCCD diffractometer	882 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.079
Graphite monochromator	θ_max = 27.7°, θ_min = 2.9°
ϕ and ω scans	h = −7→5
5318 measured reflections	k = −18→8
2377 independent reflections	l = −33→37

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	All H-atom parameters refined
S = 0.88	w = 1/[σ²(F_o²) + (0.0356P)²] where P = (F_o² + 2F_c²)/3
2377 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₄H₁₀ClNO₂	V = 2408.3 (4) Å³
M_r = 259.69	Z = 8
Orthorhombic, Pcab	Mo Kα radiation
a = 6.0014 (4) Å	µ = 0.31 mm⁻¹
b = 13.9015 (16) Å	T = 293 K
c = 28.867 (3) Å	0.19 × 0.10 × 0.08 mm

Data collection top

Nonius KappaCCD diffractometer	882 reflections with I > 2σ(I)
5318 measured reflections	R_int = 0.079
2377 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.121	All H-atom parameters refined
S = 0.88	Δρ_max = 0.14 e Å⁻³
2377 reflections	Δρ_min = −0.14 e Å⁻³
203 parameters

Special details top

Experimental. Spectroscopic data for the title compound: IR(ATR) ν_max cm^-1: 2894 (CH₂), 1600 (C=N), 1270 (C-O-C), 1490 (C=C), 827 (aromatic C-H), 789 (C-Cl) ; MS, (DIP 70 eV) for C₁₄H₁₀ClNO₂ m/z: (%): 259([M⁺],100), 261 ([M⁺²], 32), 138 (19), 121 (21), 75 (86). ₁H NMR (400 MHz, CDC_l3) δ: 8.30 (s, 1H, H-7), 7.51 (d, J= 1.6 Hz, 1H, H-9), 7.34 (d, J= 8.8 Hz, 2H,H-5,3), 7.26 (dd, J= 8.0, 1.6 Hz, 1H, H-13), 7.12 (d, J= 8.8 Hz, 2H, H-6,2), 6.88 (d, J= 8.0 Hz, 1H, H-12), 6.04 (s, 2H, H-14).¹³C NMR (100 MHz, CDCl₃)δ: 159.70 (C-7), 150.69 (C-10), 150.44 (C-11), 148.45 (C-8), 131.12 (C-4), 130.87 (C-1), 129.16 (C-5,3), 125.93 (C-13), 122.17 (C-6,2), 108.22 (C-12), 106.77 (C-9), 101.65 (C-14).

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	1.12362 (17)	0.14475 (7)	0.07300 (4)	0.0934 (5)
O1	0.5831 (4)	0.12741 (17)	0.47355 (10)	0.0907 (12)
O2	0.9308 (4)	0.07606 (17)	0.45147 (10)	0.0896 (11)
N1	0.9505 (4)	0.10652 (15)	0.27165 (11)	0.0565 (10)
C1	0.9840 (5)	0.11197 (19)	0.22375 (14)	0.0501 (14)
C2	0.8314 (6)	0.0822 (2)	0.19112 (17)	0.0583 (14)
C3	0.8719 (6)	0.0919 (2)	0.14533 (17)	0.0630 (14)
C4	1.0729 (6)	0.13107 (19)	0.13112 (13)	0.0593 (14)
C5	1.2271 (6)	0.1580 (2)	0.16245 (17)	0.0643 (16)
C6	1.1841 (5)	0.1488 (2)	0.20827 (18)	0.0593 (14)
C7	0.7604 (6)	0.1239 (2)	0.28814 (15)	0.0550 (14)
C8	0.7055 (5)	0.12225 (18)	0.33637 (13)	0.0477 (14)
C9	0.8629 (6)	0.0938 (2)	0.36895 (15)	0.0570 (14)
C10	0.8071 (6)	0.0976 (2)	0.41295 (16)	0.0623 (14)
C11	0.5986 (6)	0.1287 (2)	0.42683 (15)	0.0617 (14)
C12	0.4405 (6)	0.1554 (2)	0.39631 (15)	0.0613 (14)
C13	0.4983 (5)	0.1521 (2)	0.35034 (15)	0.0560 (14)
C14	0.7954 (9)	0.0974 (6)	0.4903 (2)	0.110 (3)
H2	0.697 (5)	0.0546 (18)	0.1998 (10)	0.066 (10)*
H3	0.772 (5)	0.073 (2)	0.1208 (12)	0.082 (11)*
H5	1.351 (4)	0.1855 (16)	0.1520 (10)	0.046 (8)*
H6	1.279 (5)	0.1725 (16)	0.2307 (11)	0.059 (10)*
H7	0.649 (4)	0.1402 (15)	0.2697 (10)	0.037 (8)*
H9	0.994 (4)	0.0776 (16)	0.3586 (10)	0.042 (8)*
H12	0.296 (5)	0.180 (2)	0.4049 (11)	0.079 (10)*
H13	0.389 (5)	0.1706 (17)	0.3261 (11)	0.065 (9)*
H14	0.851 (10)	0.150 (3)	0.507 (2)	0.20 (3)*
H14A	0.770 (6)	0.042 (2)	0.5050 (16)	0.115 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1101 (8)	0.1037 (8)	0.0663 (8)	−0.0003 (6)	0.0110 (7)	0.0115 (6)
O1	0.075 (2)	0.132 (2)	0.065 (2)	0.0176 (14)	0.0076 (17)	0.0032 (16)
O2	0.0707 (17)	0.147 (2)	0.051 (2)	0.0218 (14)	−0.0070 (17)	0.0085 (16)
N1	0.0407 (17)	0.0619 (16)	0.067 (2)	0.0055 (11)	0.0016 (15)	−0.0008 (14)
C1	0.046 (2)	0.0462 (19)	0.058 (3)	0.0047 (14)	0.004 (2)	−0.0004 (16)
C2	0.051 (2)	0.056 (2)	0.068 (3)	−0.0105 (16)	−0.004 (2)	−0.003 (2)
C3	0.063 (2)	0.066 (2)	0.060 (3)	−0.0056 (18)	−0.010 (2)	−0.007 (2)
C4	0.068 (2)	0.053 (2)	0.057 (3)	0.0078 (17)	0.001 (2)	0.0004 (17)
C5	0.050 (2)	0.065 (2)	0.078 (4)	−0.0065 (17)	0.007 (2)	0.006 (2)
C6	0.043 (2)	0.068 (2)	0.067 (3)	0.0002 (17)	−0.007 (2)	−0.006 (2)
C7	0.046 (2)	0.052 (2)	0.067 (3)	0.0027 (15)	−0.016 (2)	0.0053 (18)
C8	0.043 (2)	0.0461 (19)	0.054 (3)	0.0013 (14)	−0.0044 (18)	0.0058 (16)
C9	0.040 (2)	0.064 (2)	0.067 (3)	0.0043 (16)	0.009 (2)	0.0027 (19)
C10	0.055 (2)	0.069 (2)	0.063 (3)	0.0027 (16)	−0.001 (2)	0.005 (2)
C11	0.059 (2)	0.071 (2)	0.055 (3)	−0.0004 (17)	0.007 (2)	0.001 (2)
C12	0.046 (2)	0.066 (2)	0.072 (3)	0.0088 (18)	0.003 (2)	−0.004 (2)
C13	0.044 (2)	0.060 (2)	0.064 (3)	0.0032 (15)	−0.005 (2)	0.0007 (19)
C14	0.098 (4)	0.169 (7)	0.062 (4)	0.034 (4)	0.003 (3)	0.012 (4)

Geometric parameters (Å, º) top

Cl1—C4	1.716 (4)	C8—C13	1.372 (4)
O1—C11	1.352 (5)	C9—C10	1.315 (6)
O1—C14	1.425 (6)	C10—C11	1.383 (5)
O2—C10	1.370 (5)	C11—C12	1.347 (5)
O2—C14	1.416 (6)	C12—C13	1.372 (6)
N1—C1	1.399 (5)	C2—H2	0.93 (3)
N1—C7	1.260 (4)	C3—H3	0.96 (3)
C1—C2	1.377 (5)	C5—H5	0.89 (2)
C1—C6	1.380 (4)	C6—H6	0.92 (3)
C2—C3	1.351 (7)	C7—H7	0.88 (3)
C3—C4	1.386 (5)	C9—H9	0.87 (2)
C4—C5	1.347 (6)	C12—H12	0.97 (3)
C5—C6	1.354 (7)	C13—H13	0.99 (3)
C7—C8	1.431 (6)	C14—H14	0.94 (5)
C8—C9	1.390 (5)	C14—H14A	0.89 (3)

C11—O1—C14	106.3 (3)	C11—C12—C13	116.4 (3)
C10—O2—C14	106.6 (3)	C8—C13—C12	121.6 (3)
C1—N1—C7	119.6 (3)	O1—C14—O2	107.8 (4)
N1—C1—C2	124.3 (3)	C1—C2—H2	121.2 (18)
N1—C1—C6	117.7 (3)	C3—C2—H2	117.5 (18)
C2—C1—C6	118.0 (4)	C2—C3—H3	125 (2)
C1—C2—C3	121.3 (3)	C4—C3—H3	116 (2)
C2—C3—C4	119.1 (4)	C4—C5—H5	117.8 (19)
Cl1—C4—C3	119.2 (3)	C6—C5—H5	122.1 (19)
Cl1—C4—C5	120.3 (3)	C1—C6—H6	116.3 (19)
C3—C4—C5	120.6 (4)	C5—C6—H6	122.3 (19)
C4—C5—C6	119.9 (3)	N1—C7—H7	120.4 (18)
C1—C6—C5	121.2 (4)	C8—C7—H7	114.6 (18)
N1—C7—C8	125.0 (3)	C8—C9—H9	117.1 (19)
C7—C8—C9	120.4 (3)	C10—C9—H9	124.9 (19)
C7—C8—C13	119.3 (3)	C11—C12—H12	124.3 (19)
C9—C8—C13	120.2 (4)	C13—C12—H12	119.2 (19)
C8—C9—C10	118.0 (3)	C8—C13—H13	118.0 (18)
O2—C10—C9	129.6 (3)	C12—C13—H13	120.4 (18)
O2—C10—C11	108.9 (4)	O1—C14—H14	105 (3)
C9—C10—C11	121.5 (4)	O1—C14—H14A	105 (2)
O1—C11—C10	110.3 (3)	O2—C14—H14	112 (4)
O1—C11—C12	127.4 (3)	O2—C14—H14A	107 (3)
C10—C11—C12	122.3 (4)	H14—C14—H14A	119 (4)

C14—O1—C11—C12	−177.8 (4)	C3—C4—C5—C6	−1.5 (4)
C11—O1—C14—O2	−3.3 (6)	C4—C5—C6—C1	0.1 (4)
C14—O1—C11—C10	2.2 (5)	N1—C7—C8—C9	−4.5 (4)
C14—O2—C10—C11	−1.7 (4)	N1—C7—C8—C13	173.3 (3)
C14—O2—C10—C9	176.9 (4)	C13—C8—C9—C10	−0.7 (4)
C10—O2—C14—O1	3.1 (6)	C9—C8—C13—C12	0.4 (4)
C7—N1—C1—C6	142.4 (3)	C7—C8—C9—C10	177.1 (3)
C7—N1—C1—C2	−38.2 (4)	C7—C8—C13—C12	−177.5 (3)
C1—N1—C7—C8	−179.0 (3)	C8—C9—C10—O2	−178.4 (3)
C2—C1—C6—C5	1.8 (4)	C8—C9—C10—C11	0.1 (4)
N1—C1—C6—C5	−178.8 (3)	O2—C10—C11—O1	−0.4 (3)
N1—C1—C2—C3	178.2 (3)	O2—C10—C11—C12	179.7 (3)
C6—C1—C2—C3	−2.5 (4)	C9—C10—C11—O1	−179.1 (3)
C1—C2—C3—C4	1.2 (4)	C9—C10—C11—C12	1.0 (5)
C2—C3—C4—Cl1	−179.3 (2)	O1—C11—C12—C13	178.8 (3)
C2—C3—C4—C5	0.8 (4)	C10—C11—C12—C13	−1.3 (4)
Cl1—C4—C5—C6	178.7 (2)	C11—C12—C13—C8	0.6 (4)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀ClNO₂
M_r	259.69
Crystal system, space group	Orthorhombic, Pcab
Temperature (K)	293
a, b, c (Å)	6.0014 (4), 13.9015 (16), 28.867 (3)
V (Å³)	2408.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.19 × 0.10 × 0.08

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5318, 2377, 882
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.058, 0.121, 0.88
No. of reflections	2377
No. of parameters	203
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.14

Computer programs: COLLECT (Nonius, 1999), HKL SCALEPACK (Otwinowski & Minor 1997), HKL DENZO and SCALEPACK (Otwinowski & Minor 1997), SHELXS97 (Sheldrick 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX publication routines (Farrugia, 2012).

Acknowledgements

Financial support from CONACYT (project No. 183980) and CIC–UMSNH is gratefully acknowledged. Furthermore the authors thank CONACYT (project No. 183980) for providing a license to use the Cambridge Structural Database. Special thanks go to Marco A. Leyva-Ramírez (CINVESTAV–IPN) for the data collection.

References

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