Literature DB >> 21581960

(E)-4-Chloro-N-[(E)-2-methyl-3-phenyl-allyl-idene]aniline.

Abstract

The title Schiff base compound, C(16)H(14)ClN, adopts E configurations with respect to both the C=C and C=N bonds. The dihedral angle between the two aromatic rings is 53.27 (4)°, while the plane through the C=C-C=N system is inclined at 9.06 (8)° to the benzene ring and 44.92 (5)° to the chloro-benzene ring. In the crystal structure, weak C-H⋯Cl and C-H⋯N hydrogen bonds stack the mol-ecules down the a axis.

Entities: Chemical Disease Species

Year: 2009 PMID： 21581960 PMCID： PMC2968393 DOI： 10.1107/S1600536809001871

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to the use of Schiff bases as ligands see: Khalaji et al. (2008a ▶,b ▶); and for their bio-activity, see: Karthikeyan et al. (2006 ▶); Xiong et al. (2008 ▶); Sriram et al. (2006 ▶). For related structures, see: Khalaji et al. (2007 ▶); Khalaji & Harrison (2008 ▶); Khalaji et al. (2008c ▶). For reference structural data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H14ClN M = 255.73 Orthorhombic, a = 7.2486 (10) Å b = 11.6637 (17) Å c = 15.598 (2) Å V = 1318.7 (3) Å3 Z = 4 Mo Kα radiation μ = 0.27 mm−1 T = 89 (2) K 0.36 × 0.24 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.841, T max = 0.992 21077 measured reflections 4077 independent reflections 3517 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.109 S = 1.06 4077 reflections 164 parameters H-atom parameters constrained Δρmax = 0.30 e Å−3 Δρmin = −0.36 e Å−3 Absolute structure: Flack (1983 ▶), 1742 Friedel pairs Flack parameter: 0.01 (6) Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: APEX2 and SAINT (Bruker, 2006 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and TITAN (Hunter & Simpson, 1999 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97, enCIFer (Allen et al., 2004 ▶), PLATON (Spek, 2003 ▶) and publCIF (Westrip, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001871/pk2147sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001871/pk2147Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₆H₁₄ClN	F(000) = 536
M_r = 255.73	D_x = 1.288 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5396 reflections
a = 7.2486 (10) Å	θ = 2.6–28.8°
b = 11.6637 (17) Å	µ = 0.27 mm⁻¹
c = 15.598 (2) Å	T = 89 K
V = 1318.7 (3) Å³	Rectangular plate, pale yellow
Z = 4	0.36 × 0.24 × 0.03 mm

Bruker APEXII CCD area-detector diffractometer	4077 independent reflections
Radiation source: fine-focus sealed tube	3517 reflections with I > 2σ(I)
graphite	R_int = 0.058
ω scans	θ_max = 30.7°, θ_min = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −10→10
T_min = 0.841, T_max = 0.992	k = −16→16
21077 measured reflections	l = −21→22

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)] = 0.039	H-atom parameters constrained
wR(F²) = 0.109	w = 1/[σ²(F_o²) + (0.0649P)²] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
4077 reflections	Δρ_max = 0.30 e Å⁻³
164 parameters	Δρ_min = −0.36 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1742 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.01 (6)

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	U_iso*/U_eq
N1	0.5152 (2)	0.52967 (12)	0.68870 (9)	0.0202 (3)
C1	0.4972 (2)	0.61272 (13)	0.63497 (9)	0.0183 (3)
H1	0.4550	0.6848	0.6553	0.022*
C2	0.5394 (2)	0.60026 (13)	0.54384 (9)	0.0172 (3)
C3	0.6040 (3)	0.48397 (13)	0.51348 (10)	0.0224 (3)
H3A	0.5303	0.4601	0.4639	0.034*
H3B	0.5892	0.4280	0.5598	0.034*
H3C	0.7343	0.4884	0.4970	0.034*
C4	0.5161 (2)	0.69557 (13)	0.49535 (10)	0.0178 (3)
H4	0.4725	0.7602	0.5264	0.021*
C5	0.5458 (2)	0.71712 (13)	0.40389 (10)	0.0166 (3)
C6	0.6332 (3)	0.64156 (14)	0.34605 (10)	0.0227 (3)
H6	0.6771	0.5695	0.3659	0.027*
C7	0.6560 (2)	0.67119 (14)	0.26031 (10)	0.0228 (3)
H7	0.7151	0.6192	0.2223	0.027*
C8	0.5931 (2)	0.77606 (14)	0.22974 (10)	0.0228 (3)
H8	0.6072	0.7953	0.1709	0.027*
C9	0.5089 (3)	0.85283 (15)	0.28615 (11)	0.0243 (4)
H9	0.4672	0.9252	0.2660	0.029*
C10	0.4861 (2)	0.82324 (14)	0.37165 (10)	0.0205 (3)
H10	0.4286	0.8762	0.4094	0.025*
C11	0.4819 (2)	0.55276 (13)	0.77639 (10)	0.0182 (3)
C12	0.5526 (2)	0.64996 (13)	0.81773 (10)	0.0203 (3)
H12	0.6233	0.7040	0.7862	0.024*
C13	0.5200 (2)	0.66792 (13)	0.90454 (10)	0.0207 (3)
H13	0.5671	0.7342	0.9323	0.025*
C14	0.4183 (2)	0.58807 (13)	0.94995 (10)	0.0193 (3)
Cl1	0.38085 (6)	0.60910 (4)	1.05938 (2)	0.02595 (11)
C15	0.3494 (2)	0.48964 (13)	0.91081 (11)	0.0206 (3)
H15	0.2800	0.4354	0.9428	0.025*
C16	0.3841 (2)	0.47222 (13)	0.82400 (10)	0.0199 (3)
H16	0.3404	0.4045	0.7969	0.024*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0204 (7)	0.0212 (6)	0.0190 (6)	0.0000 (5)	0.0007 (5)	0.0002 (5)
C1	0.0174 (7)	0.0186 (6)	0.0189 (7)	0.0011 (6)	0.0001 (6)	−0.0018 (6)
C2	0.0162 (7)	0.0171 (6)	0.0182 (7)	0.0014 (6)	−0.0009 (5)	−0.0021 (6)
C3	0.0278 (9)	0.0173 (6)	0.0222 (8)	0.0029 (7)	0.0032 (7)	−0.0004 (6)
C4	0.0186 (8)	0.0163 (7)	0.0185 (7)	0.0000 (6)	0.0011 (6)	−0.0038 (5)
C5	0.0145 (7)	0.0161 (6)	0.0191 (7)	−0.0025 (6)	0.0003 (6)	−0.0018 (5)
C6	0.0291 (9)	0.0164 (6)	0.0225 (8)	0.0000 (7)	0.0035 (7)	−0.0014 (5)
C7	0.0280 (9)	0.0206 (7)	0.0199 (7)	−0.0031 (7)	0.0053 (6)	−0.0036 (6)
C8	0.0244 (9)	0.0264 (7)	0.0175 (7)	−0.0045 (7)	−0.0010 (6)	0.0008 (6)
C9	0.0257 (9)	0.0238 (7)	0.0233 (8)	0.0035 (7)	0.0006 (7)	0.0054 (6)
C10	0.0204 (8)	0.0198 (7)	0.0213 (7)	0.0028 (6)	0.0019 (6)	0.0004 (6)
C11	0.0174 (7)	0.0190 (7)	0.0183 (7)	0.0034 (6)	−0.0007 (6)	0.0014 (6)
C12	0.0209 (8)	0.0183 (6)	0.0218 (7)	−0.0003 (6)	−0.0028 (6)	0.0042 (6)
C13	0.0233 (8)	0.0174 (7)	0.0214 (7)	−0.0008 (6)	−0.0039 (6)	−0.0012 (6)
C14	0.0181 (7)	0.0217 (7)	0.0180 (7)	0.0051 (6)	−0.0004 (6)	0.0021 (6)
Cl1	0.0302 (2)	0.02978 (19)	0.01791 (17)	0.00604 (18)	0.00123 (15)	−0.00069 (15)
C15	0.0197 (8)	0.0196 (7)	0.0225 (7)	0.0009 (6)	0.0016 (6)	0.0030 (6)
C16	0.0199 (8)	0.0172 (6)	0.0228 (7)	0.0000 (6)	−0.0005 (6)	−0.0006 (6)

N1—C1	1.287 (2)	C8—C9	1.396 (2)
N1—C11	1.415 (2)	C8—H8	0.9500
C1—C2	1.4612 (19)	C9—C10	1.387 (2)
C1—H1	0.9500	C9—H9	0.9500
C2—C4	1.355 (2)	C10—H10	0.9500
C2—C3	1.511 (2)	C11—C16	1.392 (2)
C3—H3A	0.9800	C11—C12	1.401 (2)
C3—H3B	0.9800	C12—C13	1.390 (2)
C3—H3C	0.9800	C12—H12	0.9500
C4—C5	1.464 (2)	C13—C14	1.383 (2)
C4—H4	0.9500	C13—H13	0.9500
C5—C10	1.404 (2)	C14—C15	1.393 (2)
C5—C6	1.412 (2)	C14—Cl1	1.7456 (16)
C6—C7	1.391 (2)	C15—C16	1.392 (2)
C6—H6	0.9500	C15—H15	0.9500
C7—C8	1.390 (2)	C16—H16	0.9500
C7—H7	0.9500

C1—N1—C11	117.96 (14)	C7—C8—H8	120.3
N1—C1—C2	122.50 (14)	C9—C8—H8	120.3
N1—C1—H1	118.8	C10—C9—C8	119.89 (15)
C2—C1—H1	118.8	C10—C9—H9	120.1
C4—C2—C1	115.80 (14)	C8—C9—H9	120.1
C4—C2—C3	126.88 (13)	C9—C10—C5	121.79 (15)
C1—C2—C3	117.32 (13)	C9—C10—H10	119.1
C2—C3—H3A	109.5	C5—C10—H10	119.1
C2—C3—H3B	109.5	C16—C11—C12	119.14 (15)
H3A—C3—H3B	109.5	C16—C11—N1	118.32 (14)
C2—C3—H3C	109.5	C12—C11—N1	122.44 (15)
H3A—C3—H3C	109.5	C13—C12—C11	120.52 (15)
H3B—C3—H3C	109.5	C13—C12—H12	119.7
C2—C4—C5	131.77 (14)	C11—C12—H12	119.7
C2—C4—H4	114.1	C14—C13—C12	119.20 (15)
C5—C4—H4	114.1	C14—C13—H13	120.4
C10—C5—C6	117.38 (14)	C12—C13—H13	120.4
C10—C5—C4	117.05 (14)	C13—C14—C15	121.45 (15)
C6—C5—C4	125.55 (14)	C13—C14—Cl1	119.28 (12)
C7—C6—C5	120.84 (15)	C15—C14—Cl1	119.25 (12)
C7—C6—H6	119.6	C16—C15—C14	118.82 (15)
C5—C6—H6	119.6	C16—C15—H15	120.6
C8—C7—C6	120.63 (15)	C14—C15—H15	120.6
C8—C7—H7	119.7	C11—C16—C15	120.83 (14)
C6—C7—H7	119.7	C11—C16—H16	119.6
C7—C8—C9	119.46 (15)	C15—C16—H16	119.6

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···N1ⁱ	0.95	2.67	3.524 (2)	150
C13—H13···Cl1ⁱⁱ	0.95	2.92	3.7311 (17)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯N1ⁱ	0.95	2.67	3.524 (2)	150
C13—H13⋯Cl1ⁱⁱ	0.95	2.92	3.7311 (17)	144

Symmetry codes: (i) ; (ii) .

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