4-Chloro-N-(3-phenyl­allyl­idene)aniline

Zhang, B.-X.

doi:10.1107/S1600536808039391

organic compounds

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Volume 64| Part 12| December 2008| Page o2478

doi:10.1107/S1600536808039391

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4-Chloro-N-(3-phenylallylidene)aniline

Bing-Xiang Zhang ^a ^*

^aDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China
^*Correspondence e-mail: bezhbx@163.com

(Received 10 November 2008; accepted 24 November 2008; online 29 November 2008)

In the title molecule, C₁₅H₁₂ClN, the C=N and C=C bond lengths are 1.273 (2) and 1.324 (2) Å, respectively. The two aromatic rings form a dihedral angle of 3.27 (3)°.

Related literature

For a related structure, see Pu (2008 ). For general background, see: Garnovskii et al. (1993 ); Anderson et al. (1997 ); Musie et al. (2001 ); Paul et al. (2002 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₅H₁₂ClN
M_r = 241.71
Orthorhombic, P n a 2₁
a = 7.7333 (7) Å
b = 5.5957 (5) Å
c = 29.383 (3) Å
V = 1271.5 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 295 (2) K
0.15 × 0.12 × 0.08 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.960, T_max = 0.978
6043 measured reflections
2187 independent reflections
2042 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.066
S = 1.05
2187 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.09 e Å⁻³
Δρ_min = −0.15 e Å⁻³
Absolute structure: Flack (1983 ), 1031 Friedel pairs
Flack parameter: 0.07 (5)

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); 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/S1600536808039391/cv2477sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808039391/cv2477Isup2.hkl

checkCIF report

Comment top

Schiff base compounds have been of great interest for many years. These compounds play an important role in the development of coordination chemistry related to catalysis and enzymatic reactions, magnetism and molecular architectures (Garnovskii et al., 1993; Anderson et al., 1997; Musie et al., 2001; Paul et al., 2002; Pu, 2008). In order to search for new Schiff-bases with higher bioactivity, the title compound (I) was synthesized and its crystal structure determined.

In (I) (Fig. 1), the bond lengths and angles are in good agreement with the expected values (Allen et al., 1987).

Related literature top

For related crystal structure, see Pu (2008). For general background, see: Garnovskii et al. (1993); Anderson et al. (1997); Musie et al. (2001); Paul et al. (2002). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by the reaction of 4-Chloro-phenylamine (1 mmol, 127.6 mg) with 3-Phenyl-propenal(1 mmol, 132.2 mg) in ethanol(20 ml) under reflux conditions (338 K) for 5 h. The solvent was removed and the solid product recrystallized from tetrahydrofuran. After five days yellow crystals suitable for X-ray diffraction study were obtained.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (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 (I), with displacement ellipsoids drawn at the 30% probability level.

4-Chloro-N-(3-phenylallylidene)aniline top

Crystal data top

C₁₅H₁₂ClN	F(000) = 504
M_r = 241.71	D_x = 1.263 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 3328 reflections
a = 7.7333 (7) Å	θ = 2.7–27.2°
b = 5.5957 (5) Å	µ = 0.28 mm⁻¹
c = 29.383 (3) Å	T = 295 K
V = 1271.5 (2) Å³	Block, yellow
Z = 4	0.15 × 0.12 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2187 independent reflections
Radiation source: fine-focus sealed tube	2042 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.960, T_max = 0.978	k = −6→4
6043 measured reflections	l = −32→35

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	w = 1/[σ²(F_o²) + (0.0375P)² + 0.0706P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
2187 reflections	Δρ_max = 0.09 e Å⁻³
154 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1031 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.07 (5)

Crystal data top

C₁₅H₁₂ClN	V = 1271.5 (2) Å³
M_r = 241.71	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.7333 (7) Å	µ = 0.28 mm⁻¹
b = 5.5957 (5) Å	T = 295 K
c = 29.383 (3) Å	0.15 × 0.12 × 0.08 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2187 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2042 reflections with I > 2σ(I)
T_min = 0.960, T_max = 0.978	R_int = 0.016
6043 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	H-atom parameters constrained
wR(F²) = 0.066	Δρ_max = 0.09 e Å⁻³
S = 1.06	Δρ_min = −0.15 e Å⁻³
2187 reflections	Absolute structure: Flack (1983), 1031 Friedel pairs
154 parameters	Absolute structure parameter: 0.07 (5)
0 restraints

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	0.65759 (7)	0.44278 (11)	0.969692 (18)	0.08065 (18)
N1	0.87735 (18)	0.5317 (3)	0.77774 (5)	0.0522 (3)
C1	0.7249 (2)	0.4739 (3)	0.91350 (6)	0.0509 (4)
C2	0.8238 (2)	0.6663 (3)	0.90138 (5)	0.0535 (4)
H2	0.8555	0.7795	0.9230	0.064*
C3	0.8761 (2)	0.6907 (3)	0.85660 (5)	0.0503 (4)
H3	0.9443	0.8203	0.8483	0.060*
C4	0.82813 (19)	0.5241 (3)	0.82396 (6)	0.0430 (3)
C5	0.7294 (2)	0.3300 (3)	0.83740 (6)	0.0483 (4)
H5	0.6984	0.2152	0.8160	0.058*
C6	0.6762 (2)	0.3037 (3)	0.88200 (6)	0.0524 (4)
H6	0.6088	0.1737	0.8906	0.063*
C7	0.9240 (2)	0.7278 (3)	0.75959 (6)	0.0499 (4)
H7	0.9253	0.8657	0.7773	0.060*
C8	0.9747 (2)	0.7431 (3)	0.71272 (5)	0.0477 (3)
H8	0.9650	0.6067	0.6948	0.057*
C9	1.0343 (2)	0.9406 (3)	0.69352 (5)	0.0504 (4)
H9	1.0425	1.0744	0.7122	0.060*
C10	1.0884 (2)	0.9711 (3)	0.64651 (5)	0.0421 (3)
C11	1.1805 (2)	1.1742 (3)	0.63356 (5)	0.0493 (4)
H11	1.2065	1.2901	0.6552	0.059*
C12	1.2339 (2)	1.2059 (3)	0.58897 (6)	0.0541 (4)
H12	1.2960	1.3419	0.5810	0.065*
C13	1.1957 (2)	1.0385 (3)	0.55664 (6)	0.0531 (4)
H13	1.2307	1.0608	0.5267	0.064*
C14	1.1043 (2)	0.8352 (3)	0.56881 (5)	0.0505 (4)
H14	1.0791	0.7201	0.5470	0.061*
C15	1.0509 (2)	0.8028 (3)	0.61284 (5)	0.0452 (3)
H15	0.9886	0.6664	0.6204	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0921 (4)	0.1047 (4)	0.0451 (2)	−0.0037 (3)	0.0100 (2)	0.0165 (3)
N1	0.0539 (8)	0.0588 (8)	0.0439 (8)	−0.0028 (6)	0.0035 (6)	0.0003 (6)
C1	0.0462 (9)	0.0647 (11)	0.0417 (8)	0.0070 (8)	0.0009 (7)	0.0096 (8)
C2	0.0597 (10)	0.0562 (10)	0.0448 (9)	−0.0048 (8)	−0.0048 (7)	−0.0015 (8)
C3	0.0522 (9)	0.0502 (9)	0.0487 (9)	−0.0114 (8)	−0.0012 (7)	0.0045 (8)
C4	0.0383 (7)	0.0467 (8)	0.0441 (8)	0.0020 (6)	−0.0021 (7)	0.0021 (7)
C5	0.0484 (9)	0.0431 (8)	0.0535 (9)	−0.0021 (7)	0.0010 (7)	−0.0011 (7)
C6	0.0496 (9)	0.0503 (9)	0.0573 (10)	−0.0071 (7)	0.0031 (8)	0.0092 (8)
C7	0.0480 (8)	0.0569 (9)	0.0448 (8)	0.0002 (7)	−0.0011 (7)	0.0019 (7)
C8	0.0464 (8)	0.0556 (9)	0.0412 (7)	−0.0002 (7)	−0.0005 (7)	−0.0001 (6)
C9	0.0534 (9)	0.0527 (9)	0.0450 (8)	−0.0019 (7)	−0.0028 (7)	−0.0021 (7)
C10	0.0392 (7)	0.0449 (8)	0.0423 (8)	0.0034 (6)	−0.0041 (6)	0.0052 (6)
C11	0.0499 (9)	0.0444 (8)	0.0537 (9)	−0.0028 (7)	−0.0055 (7)	0.0005 (7)
C12	0.0515 (10)	0.0483 (9)	0.0625 (11)	−0.0021 (7)	0.0037 (8)	0.0143 (8)
C13	0.0553 (10)	0.0565 (10)	0.0477 (10)	0.0064 (7)	0.0035 (7)	0.0099 (8)
C14	0.0584 (10)	0.0500 (9)	0.0432 (9)	0.0057 (7)	−0.0044 (7)	−0.0017 (7)
C15	0.0481 (8)	0.0426 (7)	0.0449 (8)	−0.0032 (7)	−0.0052 (7)	0.0041 (7)

Geometric parameters (Å, º) top

Cl1—C1	1.7399 (17)	C8—C9	1.324 (2)
N1—C7	1.273 (2)	C8—H8	0.9300
N1—C4	1.411 (2)	C9—C10	1.454 (2)
C1—C2	1.368 (2)	C9—H9	0.9300
C1—C6	1.380 (3)	C10—C11	1.394 (2)
C2—C3	1.383 (2)	C10—C15	1.397 (2)
C2—H2	0.9300	C11—C12	1.385 (2)
C3—C4	1.388 (2)	C11—H11	0.9300
C3—H3	0.9300	C12—C13	1.367 (3)
C4—C5	1.385 (2)	C12—H12	0.9300
C5—C6	1.382 (2)	C13—C14	1.386 (3)
C5—H5	0.9300	C13—H13	0.9300
C6—H6	0.9300	C14—C15	1.370 (2)
C7—C8	1.434 (2)	C14—H14	0.9300
C7—H7	0.9300	C15—H15	0.9300

C7—N1—C4	120.37 (14)	C9—C8—H8	118.2
C2—C1—C6	121.41 (16)	C7—C8—H8	118.2
C2—C1—Cl1	119.54 (14)	C8—C9—C10	127.14 (15)
C6—C1—Cl1	119.05 (14)	C8—C9—H9	116.4
C1—C2—C3	119.25 (16)	C10—C9—H9	116.4
C1—C2—H2	120.4	C11—C10—C15	117.55 (14)
C3—C2—H2	120.4	C11—C10—C9	120.17 (14)
C2—C3—C4	120.87 (15)	C15—C10—C9	122.27 (14)
C2—C3—H3	119.6	C12—C11—C10	121.00 (15)
C4—C3—H3	119.6	C12—C11—H11	119.5
C5—C4—C3	118.49 (15)	C10—C11—H11	119.5
C5—C4—N1	116.52 (14)	C13—C12—C11	120.35 (16)
C3—C4—N1	124.95 (14)	C13—C12—H12	119.8
C6—C5—C4	121.20 (15)	C11—C12—H12	119.8
C6—C5—H5	119.4	C12—C13—C14	119.57 (15)
C4—C5—H5	119.4	C12—C13—H13	120.2
C5—C6—C1	118.77 (15)	C14—C13—H13	120.2
C5—C6—H6	120.6	C15—C14—C13	120.39 (15)
C1—C6—H6	120.6	C15—C14—H14	119.8
N1—C7—C8	122.08 (15)	C13—C14—H14	119.8
N1—C7—H7	119.0	C14—C15—C10	121.14 (14)
C8—C7—H7	119.0	C14—C15—H15	119.4
C9—C8—C7	123.66 (15)	C10—C15—H15	119.4

C6—C1—C2—C3	0.0 (3)	N1—C7—C8—C9	−175.51 (17)
Cl1—C1—C2—C3	−179.67 (13)	C7—C8—C9—C10	179.94 (15)
C1—C2—C3—C4	0.6 (2)	C8—C9—C10—C11	−166.99 (16)
C2—C3—C4—C5	−1.3 (2)	C8—C9—C10—C15	13.3 (3)
C2—C3—C4—N1	−178.92 (16)	C15—C10—C11—C12	−0.6 (2)
C7—N1—C4—C5	160.20 (15)	C9—C10—C11—C12	179.69 (15)
C7—N1—C4—C3	−22.1 (2)	C10—C11—C12—C13	0.5 (3)
C3—C4—C5—C6	1.3 (2)	C11—C12—C13—C14	−0.6 (3)
N1—C4—C5—C6	179.18 (14)	C12—C13—C14—C15	0.7 (2)
C4—C5—C6—C1	−0.7 (2)	C13—C14—C15—C10	−0.7 (2)
C2—C1—C6—C5	0.1 (2)	C11—C10—C15—C14	0.7 (2)
Cl1—C1—C6—C5	179.73 (13)	C9—C10—C15—C14	−179.60 (15)
C4—N1—C7—C8	−179.89 (14)

Experimental details

Crystal data
Chemical formula	C₁₅H₁₂ClN
M_r	241.71
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	295
a, b, c (Å)	7.7333 (7), 5.5957 (5), 29.383 (3)
V (Å³)	1271.5 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.15 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.960, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	6043, 2187, 2042
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.066, 1.06
No. of reflections	2187
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.09, −0.15
Absolute structure	Flack (1983), 1031 Friedel pairs
Absolute structure parameter	0.07 (5)

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

Acknowledgements

This project was supported by the Postgraduate Foundation of Taishan University (grant No. Y03–1–13).

References

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