4-Chloro-N-(3,4,5-trimethoxy­benzyl­idene)aniline

Dehno Khalaji, A.; Asghari, J.; Fejfarová, K.; Dušek, M.

doi:10.1107/S1600536809000300

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o253

doi:10.1107/S1600536809000300

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4-Chloro-N-(3,4,5-trimethoxybenzylidene)aniline

Aliakbar Dehno Khalaji,^a Jilla Asghari,^a Karla Fejfarová ^b and Michal Dušek ^b ^*

^aDepartment of Science, Gorgan University of Agricultural Sciences and Natural Resources, Gorgan 49189-43464, Iran, and ^bInstitute of Physics of the ASCR, Na Slovance 2, 182 21 Prague 8, Czech Republic
^*Correspondence e-mail: dusek@fzu.cz

(Received 22 December 2008; accepted 5 January 2009; online 8 January 2009)

The title compound, C₁₆H₁₆ClNO₃, is a Schiff base displaying a trans configuration of the C=N double bond. In the crystal structure, intermolecular C—H⋯N and bifurcated C—H⋯(O,O) hydrogen bonds are observed.

Related literature

For backgroud and related structures, see: Khalaji et al. (2008 ); Khalaji & Harrison (2008 ); Khalaji et al. (2007 ); Zhang (2008 ); Akkurt et al. (2008 ); Kashmiri et al. (2008 ); Ren & Jian (2008 ). For the synthesis of the title compound, see: Khalaji & Ng (2008 ).

Experimental

Crystal data

C₁₆H₁₆ClNO₃
M_r = 305.75
Monoclinic, P 2₁
a = 7.2012 (2) Å
b = 8.18700 (10) Å
c = 12.9734 (3) Å
β = 105.050 (2)°
V = 738.63 (3) Å³
Z = 2
Cu Kα radiation
μ = 2.37 mm⁻¹
T = 120 K
0.22 × 0.20 × 0.11 mm

Data collection

Oxford Diffraction Gemini diffractometer
Absorption correction: numerical [Clark & Reid (1995 ) in CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Oxford, England.]$ )] T_min = 0.680, T_max = 0.809
5670 measured reflections
2225 independent reflections
2039 reflections with I > 3σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.109
S = 1.93
2225 reflections
189 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 915 Friedel pairs
Flack parameter: 0.06 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.96	2.59	3.177 (4)	119
C7—H7⋯O2ⁱ	0.96	2.51	3.471 (4)	178
C12—H12⋯N1ⁱⁱ	0.96	2.61	3.545 (5)	164
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2005 $[Oxford Diffraction (2005). CrysAlis CCD. Oxford Diffraction Ltd, Oxford, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Oxford, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2007 ); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000300/bt2844sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000300/bt2844Isup2.hkl

checkCIF report

Comment top

Studies on the Schiff-base compounds, products of condensation between aldehydes (or ketones) and amines, have received a lot of attention in recent years, (Khalaji et al., 2008; Khalaji & Harrison, 2008; Khalaji et al.,2007; Zhang, 2008; Akkurt et al., 2008; Kashmiri et al., 2008; Ren & Jian, 2008). As a continuation of these studies we present the crystal structure of C₁₆H₁₆ClNO₃.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths and angles are comparable with those observed in similar compounds (Khalaji et al., 2008; Khalaji & Harrison, 2008; Khalaji et al.,2007; Zhang, 2008; Akkurt et al., 2008; Kashmiri et al., 2008; Ren & Jian, 2008). In the crystal structure, intermolecular C—H···N and C—H···O hydrogen bonds are observed.

Related literature top

For backgroud and related structures, see: Khalaji et al. (2008); Khalaji & Harrison (2008); Khalaji et al. (2007); Zhang (2008); Akkurt et al. (2008); Kashmiri et al. (2008); Ren & Jian (2008). For the synthesis of the title compound, see: Khalaji & Ng (2008).

Experimental top

The title compound was synthesized using a method analogous to the literature procedure of Khalaji and Ng (2008). Crystals appropriate for data collection were obtained by slow evaporation from methanol-chloroform (1:5 v/v) at a room temperature (yield 83%).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2007).

Figures top

	Fig. 1. The molecular structure of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The packing of (I) viewed along a, with hydrogen bonds shown as dashed lines.

4-Chloro-N-(3,4,5-trimethoxybenzylidene)aniline top

Crystal data top

C₁₆H₁₆ClNO₃	F(000) = 320
M_r = 305.75	D_x = 1.379 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2yb	Cell parameters from 4239 reflections
a = 7.2012 (2) Å	θ = 3.5–62.6°
b = 8.1870 (1) Å	µ = 2.37 mm⁻¹
c = 12.9734 (3) Å	T = 120 K
β = 105.050 (2)°	Prism, colorless
V = 738.63 (3) Å³	0.22 × 0.20 × 0.11 mm
Z = 2

Data collection top

Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source	2225 independent reflections
Radiation source: X-ray tube	2039 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.048
Detector resolution: 20.7567 pixels mm^-1	θ_max = 62.7°, θ_min = 3.5°
rotation method data acquisition using ω scans	h = −8→7
Absorption correction: numerical [based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]	k = −9→9
T_min = 0.680, T_max = 0.809	l = −14→14
5670 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.045	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
wR(F²) = 0.109	(Δ/σ)_max = 0.013
S = 1.93	Δρ_max = 0.28 e Å⁻³
2225 reflections	Δρ_min = −0.21 e Å⁻³
189 parameters	Absolute structure: Flack (1983), 915 Friedel pairs
0 restraints	Absolute structure parameter: 0.06 (2)
65 constraints

Crystal data top

C₁₆H₁₆ClNO₃	V = 738.63 (3) Å³
M_r = 305.75	Z = 2
Monoclinic, P2₁	Cu Kα radiation
a = 7.2012 (2) Å	µ = 2.37 mm⁻¹
b = 8.1870 (1) Å	T = 120 K
c = 12.9734 (3) Å	0.22 × 0.20 × 0.11 mm
β = 105.050 (2)°

Data collection top

Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source	2225 independent reflections
Absorption correction: numerical [based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]	2039 reflections with I > 3σ(I)
T_min = 0.680, T_max = 0.809	R_int = 0.048
5670 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.109	Δρ_max = 0.28 e Å⁻³
S = 1.93	Δρ_min = −0.21 e Å⁻³
2225 reflections	Absolute structure: Flack (1983), 915 Friedel pairs
189 parameters	Absolute structure parameter: 0.06 (2)
0 restraints

Special details top

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cl1	0.00790 (13)	0.16442 (1)	0.00937 (6)	0.0366 (3)
O1	1.2823 (3)	0.6425 (3)	0.64185 (15)	0.0252 (7)
O2	1.4726 (3)	0.8288 (3)	0.53638 (16)	0.0255 (7)
O3	1.3717 (3)	0.8527 (3)	0.32476 (16)	0.0298 (8)
N1	0.7360 (4)	0.5116 (4)	0.2085 (2)	0.0261 (10)
C1	1.2081 (4)	0.6506 (4)	0.5342 (2)	0.0199 (9)
C2	1.3141 (5)	0.7435 (4)	0.4792 (2)	0.0220 (10)
C3	1.2528 (5)	0.7593 (4)	0.3685 (3)	0.0226 (11)
C4	1.0855 (4)	0.6828 (4)	0.3111 (2)	0.0239 (10)
C5	0.9789 (5)	0.5918 (4)	0.3668 (2)	0.0212 (10)
C6	1.0392 (5)	0.5747 (4)	0.4767 (2)	0.0226 (11)
C7	0.7985 (5)	0.5127 (4)	0.3104 (2)	0.0226 (10)
C8	0.5578 (5)	0.4334 (4)	0.1638 (2)	0.0240 (10)
C9	0.4039 (4)	0.4350 (4)	0.2092 (2)	0.0250 (11)
C10	0.2330 (5)	0.3568 (4)	0.1612 (2)	0.0263 (11)
C11	0.2161 (5)	0.2724 (4)	0.0662 (2)	0.0273 (11)
C12	0.3676 (5)	0.2727 (4)	0.0172 (3)	0.0324 (12)
C13	0.5356 (5)	0.3535 (5)	0.0654 (2)	0.0315 (12)
C14	1.1767 (5)	0.5531 (5)	0.7017 (3)	0.0370 (13)
C15	1.6479 (5)	0.7425 (5)	0.5441 (3)	0.0319 (12)
C16	1.3098 (5)	0.8853 (5)	0.2132 (3)	0.0366 (14)
H4	1.043968	0.692286	0.234845	0.0286*
H6	0.964788	0.510597	0.51341	0.0271*
H9	0.415976	0.491463	0.275474	0.03*
H10	0.126966	0.360818	0.193233	0.0316*
H12	0.354653	0.217079	−0.049398	0.0389*
H13	0.638975	0.355215	0.031235	0.0378*
H14a	1.230813	0.572264	0.776497	0.0444*
H14b	1.044923	0.588152	0.682085	0.0444*
H14c	1.182975	0.43867	0.686918	0.0444*
H15a	1.753739	0.805308	0.585471	0.0382*
H15b	1.643203	0.638974	0.578074	0.0382*
H15c	1.664554	0.725127	0.473844	0.0382*
H16a	1.401652	0.954863	0.192956	0.0439*
H16b	1.299241	0.784387	0.174383	0.0439*
H16c	1.186828	0.938464	0.197126	0.0439*
H7	0.723679	0.459098	0.351803	0.0271*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0321 (4)	0.0363 (4)	0.0337 (4)	−0.0062 (4)	−0.0049 (3)	−0.0031 (4)
O1	0.0277 (12)	0.0274 (12)	0.0184 (10)	−0.0043 (10)	0.0021 (8)	−0.0007 (9)
O2	0.0210 (12)	0.0256 (12)	0.0276 (11)	−0.0031 (9)	0.0023 (9)	−0.0061 (9)
O3	0.0298 (13)	0.0353 (12)	0.0235 (11)	−0.0092 (11)	0.0054 (10)	0.0014 (10)
N1	0.0248 (16)	0.0292 (15)	0.0227 (15)	−0.0020 (12)	0.0032 (12)	−0.0012 (11)
C1	0.0216 (16)	0.0189 (14)	0.0184 (14)	0.0012 (14)	0.0039 (11)	−0.0004 (13)
C2	0.0190 (16)	0.0203 (15)	0.0239 (17)	−0.0012 (13)	0.0007 (13)	−0.0033 (12)
C3	0.0235 (18)	0.0192 (17)	0.0280 (17)	−0.0008 (13)	0.0115 (14)	0.0002 (12)
C4	0.0229 (17)	0.0235 (17)	0.0235 (15)	0.0008 (14)	0.0030 (12)	0.0005 (13)
C5	0.0182 (18)	0.0199 (15)	0.0251 (17)	0.0011 (12)	0.0046 (14)	−0.0007 (12)
C6	0.0239 (19)	0.0209 (17)	0.0227 (17)	0.0018 (13)	0.0057 (13)	0.0015 (12)
C7	0.0211 (17)	0.0200 (16)	0.0251 (17)	−0.0003 (13)	0.0033 (13)	−0.0005 (13)
C8	0.0263 (17)	0.0220 (16)	0.0206 (16)	−0.0015 (15)	0.0007 (13)	−0.0004 (13)
C9	0.0252 (18)	0.0281 (18)	0.0201 (16)	0.0027 (15)	0.0032 (13)	0.0004 (13)
C10	0.0254 (19)	0.0296 (18)	0.0219 (17)	0.0010 (14)	0.0024 (13)	0.0003 (14)
C11	0.034 (2)	0.0230 (16)	0.0191 (16)	0.0008 (14)	−0.0037 (14)	0.0007 (12)
C12	0.032 (2)	0.0353 (19)	0.0270 (18)	0.0025 (16)	0.0020 (15)	−0.0050 (14)
C13	0.032 (2)	0.040 (2)	0.0226 (17)	−0.0018 (16)	0.0080 (14)	−0.0030 (15)
C14	0.035 (2)	0.048 (2)	0.0262 (19)	−0.0060 (18)	0.0048 (15)	0.0083 (16)
C15	0.0185 (18)	0.0334 (18)	0.040 (2)	0.0021 (15)	0.0018 (15)	0.0018 (15)
C16	0.042 (2)	0.043 (2)	0.0260 (18)	−0.0086 (17)	0.0097 (16)	0.0074 (15)

Geometric parameters (Å, º) top

Cl1—C10	2.708 (3)	C7—H7	0.96
Cl1—C11	1.732 (3)	C8—C9	1.384 (5)
Cl1—C12	2.714 (4)	C8—C13	1.406 (5)
O1—C1	1.362 (3)	C9—C10	1.383 (4)
O1—C14	1.423 (5)	C9—H9	0.96
O2—C2	1.379 (4)	C10—C11	1.390 (5)
O2—C15	1.427 (4)	C10—H10	0.96
O3—C3	1.375 (4)	C11—C12	1.398 (6)
O3—C16	1.424 (4)	C12—C13	1.378 (5)
N1—C7	1.282 (4)	C12—H12	0.96
N1—C8	1.417 (4)	C13—H13	0.96
C1—C2	1.397 (5)	C14—H14a	0.96
C1—C6	1.397 (4)	C14—H14b	0.96
C2—C3	1.395 (4)	C14—H14c	0.96
C3—C4	1.390 (4)	C15—H15a	0.96
C4—C5	1.398 (5)	C15—H15b	0.96
C4—H4	0.96	C15—H15c	0.96
C5—C6	1.385 (4)	C16—H16a	0.96
C5—C7	1.466 (4)	C16—H16b	0.96
C6—H6	0.96	C16—H16c	0.96

C10—Cl1—C12	52.95 (11)	C8—C9—H9	119.2976
C1—O1—C14	117.5 (2)	C10—C9—H9	119.2983
C2—O2—C15	112.4 (3)	C9—C10—C11	119.5 (3)
C3—O3—C16	117.3 (2)	C9—C10—H10	120.2657
C7—N1—C8	117.6 (3)	C11—C10—H10	120.265
O1—C1—C2	115.4 (3)	C10—C11—C12	120.2 (3)
O1—C1—C6	125.5 (3)	C11—C12—C13	119.5 (3)
C2—C1—C6	119.0 (3)	C11—C12—H12	120.2721
O2—C2—C1	119.1 (3)	C13—C12—H12	120.2719
O2—C2—C3	120.3 (3)	C8—C13—C12	120.9 (4)
C1—C2—C3	120.5 (3)	C8—C13—H13	119.5347
O3—C3—C2	114.3 (3)	C12—C13—H13	119.5353
O3—C3—C4	125.1 (3)	O1—C14—H14a	109.4713
C2—C3—C4	120.5 (3)	O1—C14—H14b	109.4711
C3—C4—C5	118.6 (3)	O1—C14—H14c	109.4713
C3—C4—H4	120.6757	H14a—C14—H14b	109.4712
C5—C4—H4	120.6756	H14a—C14—H14c	109.4714
C4—C5—C6	121.2 (3)	H14b—C14—H14c	109.471
C4—C5—C7	120.8 (3)	O2—C15—H15a	109.4714
C6—C5—C7	118.0 (3)	O2—C15—H15b	109.4711
C1—C6—C5	120.1 (3)	O2—C15—H15c	109.4715
C1—C6—H6	119.9695	H15a—C15—H15b	109.4705
C5—C6—H6	119.9698	H15a—C15—H15c	109.4714
N1—C7—C5	123.1 (3)	H15b—C15—H15c	109.4714
N1—C7—H7	118.4336	O3—C16—H16a	109.4709
C5—C7—H7	118.4335	O3—C16—H16b	109.4714
N1—C8—C9	124.2 (3)	O3—C16—H16c	109.4711
N1—C8—C13	117.3 (3)	H16a—C16—H16b	109.4712
C9—C8—C13	118.4 (3)	H16a—C16—H16c	109.4712
C8—C9—C10	121.4 (3)	H16b—C16—H16c	109.4715

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.96	2.59	3.177 (4)	119
C7—H7···O2ⁱ	0.96	2.51	3.471 (4)	178
C12—H12···N1ⁱⁱ	0.96	2.61	3.545 (5)	164

Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+1, y−1/2, −z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClNO₃
M_r	305.75
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	120
a, b, c (Å)	7.2012 (2), 8.1870 (1), 12.9734 (3)
β (°)	105.050 (2)
V (Å³)	738.63 (3)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	2.37
Crystal size (mm)	0.22 × 0.20 × 0.11

Data collection
Diffractometer	Oxford Diffraction Gemini diffractometer with Xcalibur goniometer, Atlas detector and Gemini ultra Cu source
Absorption correction	Numerical [based on the crystal shape, using the method implemented in CrysAlis RED (Oxford Diffraction, 2008) according to Clark & Reid (1995)]
T_min, T_max	0.680, 0.809
No. of measured, independent and observed [I > 3σ(I)] reflections	5670, 2225, 2039
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.576

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.109, 1.93
No. of reflections	2225
No. of parameters	189
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21
Absolute structure	Flack (1983), 915 Friedel pairs
Absolute structure parameter	0.06 (2)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2008), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2007), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top

Cl1—C10	2.708 (3)	C1—C6	1.397 (4)
Cl1—C11	1.732 (3)	C2—C3	1.395 (4)
Cl1—C12	2.714 (4)	C3—C4	1.390 (4)
O1—C1	1.362 (3)	C4—C5	1.398 (5)
O1—C14	1.423 (5)	C5—C6	1.385 (4)
O2—C2	1.379 (4)	C5—C7	1.466 (4)
O2—C15	1.427 (4)	C8—C9	1.384 (5)
O3—C3	1.375 (4)	C8—C13	1.406 (5)
O3—C16	1.424 (4)	C9—C10	1.383 (4)
N1—C7	1.282 (4)	C10—C11	1.390 (5)
N1—C8	1.417 (4)	C11—C12	1.398 (6)
C1—C2	1.397 (5)	C12—C13	1.378 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.96	2.59	3.177 (4)	119
C7—H7···O2ⁱ	0.96	2.51	3.471 (4)	178
C12—H12···N1ⁱⁱ	0.96	2.61	3.545 (5)	164

Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+1, y−1/2, −z.

Acknowledgements

We thank Gorgan University of Agricultural Sciences and Natural Resources (GUASNR) and the Institute of Physics of the ASCR (grant No 202/07/J007) for supporting this study. ADK thanks Dr Jan Fabry (Institute of Physics of ASCR) for his collaboration.

References

Akkurt, M., Jarrahpour, A. A., Aye, M., Gençaslan, M. & Büyükgüngör, O. (2008). Acta Cryst. E64, o2175–o2176. Web of Science CSD CrossRef IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
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