Literature DB >> 22904867

N-[(E)-4-Fluoro-benzyl-idene]-3,4-di-methyl-aniline.

Yue-Bao Jin¹, Yong-Kang Chang, Ying Zhang, Ke-Wei Lei.

Abstract

In the title Schiff base, C(15)H(14)FN, the N=C bond length of 1.263 (2) Å is shorter than the N-C bond [1.426 (2) Å], indicating a typical imine double bond. Moreover, the C-N-C angle is 118.5 (2)°. The benzene rings form a dihedral angle of 51.22 (5)°.

Entities: Chemical Disease Gene

Year: 2012 PMID： 22904867 PMCID： PMC3414334 DOI： 10.1107/S1600536812030474

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

Related literature

For general background on the use of Schiff bases as ligands in inorganic and organometallic chemistry, see: Xia et al. (2009 ▶); Harries & Orford (1983 ▶); Rodriguez de Barbarin et al. (1994 ▶). For similar structures, see: Xia et al. (2009 ▶); Lindeman et al. (1981 ▶). For a related synthetic procedure, see: Chen et al. (2005 ▶).

Experimental

Crystal data

C15H14FN M = 227.27 Orthorhombic, a = 7.7487 (3) Å b = 11.3404 (3) Å c = 14.2969 (4) Å V = 1256.31 (7) Å3 Z = 4 Mo Kα radiation μ = 0.08 mm−1 T = 293 K 0.42 × 0.21 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.978, T max = 0.988 10903 measured reflections 1941 independent reflections 1476 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.040 wR(F 2) = 0.103 S = 1.05 1941 reflections 154 parameters H-atom parameters constrained Δρmax = 0.10 e Å−3 Δρmin = −0.15 e Å−3 Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030474/im2381sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030474/im2381Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812030474/im2381Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄FN	F(000) = 480
M_r = 227.27	D_x = 1.202 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4863 reflections
a = 7.7487 (3) Å	θ = 1.0–29.1°
b = 11.3404 (3) Å	µ = 0.08 mm⁻¹
c = 14.2969 (4) Å	T = 293 K
V = 1256.31 (7) Å³	Block, yellow
Z = 4	0.42 × 0.21 × 0.16 mm

Rigaku R-AXIS RAPID diffractometer	1941 independent reflections
Radiation source: fine-focus sealed tube	1476 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
ω scans	θ_max = 29.1°, θ_min = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −9→10
T_min = 0.978, T_max = 0.988	k = −14→14
10903 measured reflections	l = −18→18

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0515P)² + 0.1023P] where P = (F_o² + 2F_c²)/3
1941 reflections	(Δ/σ)_max = 0.001
154 parameters	Δρ_max = 0.10 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

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	0.5157 (2)	0.33118 (14)	0.66820 (10)	0.0529 (4)
F1	0.3419 (2)	0.37162 (14)	1.10226 (9)	0.0933 (5)
C6	0.5091 (2)	0.27263 (16)	0.50536 (13)	0.0487 (4)
H3A	0.4576	0.2024	0.5241	0.058*
C1	0.5509 (2)	0.35665 (15)	0.57238 (12)	0.0472 (4)
C10	0.4210 (2)	0.39849 (16)	0.81944 (13)	0.0502 (4)
C4	0.6225 (2)	0.39542 (17)	0.38272 (12)	0.0503 (4)
C12	0.4505 (3)	0.28949 (19)	0.96341 (15)	0.0638 (5)
H7A	0.4877	0.2234	0.9962	0.077*
C7	0.4517 (2)	0.41157 (16)	0.71858 (13)	0.0517 (4)
H8A	0.4225	0.4827	0.6904	0.062*
C5	0.5424 (2)	0.29105 (16)	0.41079 (12)	0.0488 (4)
C15	0.3412 (3)	0.48874 (18)	0.86852 (14)	0.0636 (5)
H10A	0.3062	0.5563	0.8368	0.076*
C2	0.6304 (2)	0.46021 (16)	0.54411 (13)	0.0534 (4)
H11A	0.6600	0.5173	0.5880	0.064*
C14	0.3125 (3)	0.4801 (2)	0.96400 (16)	0.0696 (6)
H12A	0.2571	0.5401	0.9967	0.083*
C9	0.6641 (3)	0.4191 (2)	0.28139 (13)	0.0715 (6)
H13A	0.7189	0.4948	0.2758	0.107*
H13B	0.5596	0.4187	0.2454	0.107*
H13C	0.7405	0.3591	0.2585	0.107*
C13	0.3683 (3)	0.3808 (2)	1.00840 (13)	0.0629 (6)
C11	0.4761 (3)	0.29881 (17)	0.86783 (13)	0.0571 (5)
H15A	0.5306	0.2380	0.8357	0.068*
C3	0.6656 (2)	0.47809 (16)	0.45035 (13)	0.0547 (4)
H16A	0.7197	0.5476	0.4321	0.066*
C8	0.4925 (3)	0.19754 (19)	0.34034 (14)	0.0686 (6)
H17A	0.4392	0.1325	0.3721	0.103*
H17B	0.5939	0.1705	0.3082	0.103*
H17C	0.4129	0.2303	0.2959	0.103*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0567 (9)	0.0536 (8)	0.0484 (8)	−0.0007 (8)	0.0001 (7)	0.0004 (6)
F1	0.1076 (11)	0.1181 (12)	0.0544 (7)	−0.0131 (10)	0.0177 (8)	−0.0034 (7)
C6	0.0467 (9)	0.0448 (9)	0.0546 (10)	−0.0030 (8)	0.0043 (8)	0.0006 (7)
C1	0.0444 (9)	0.0478 (9)	0.0495 (9)	0.0035 (7)	−0.0015 (8)	0.0031 (7)
C10	0.0439 (9)	0.0534 (9)	0.0532 (10)	−0.0025 (8)	−0.0008 (8)	−0.0032 (8)
C4	0.0431 (9)	0.0556 (10)	0.0521 (10)	0.0019 (8)	−0.0011 (8)	0.0055 (8)
C12	0.0736 (13)	0.0594 (11)	0.0584 (11)	−0.0070 (11)	−0.0023 (11)	0.0069 (9)
C7	0.0494 (10)	0.0533 (10)	0.0525 (10)	0.0010 (8)	−0.0048 (8)	0.0036 (8)
C5	0.0407 (9)	0.0535 (10)	0.0521 (10)	0.0003 (8)	0.0012 (8)	−0.0025 (8)
C15	0.0624 (12)	0.0614 (11)	0.0669 (12)	0.0131 (11)	0.0063 (11)	−0.0003 (10)
C2	0.0556 (11)	0.0486 (9)	0.0560 (10)	−0.0047 (8)	−0.0050 (9)	−0.0011 (8)
C14	0.0643 (12)	0.0753 (13)	0.0691 (13)	0.0067 (12)	0.0145 (11)	−0.0122 (11)
C9	0.0788 (14)	0.0785 (14)	0.0573 (12)	−0.0087 (13)	0.0069 (12)	0.0099 (10)
C13	0.0626 (12)	0.0767 (14)	0.0492 (10)	−0.0163 (12)	0.0079 (10)	−0.0067 (9)
C11	0.0664 (12)	0.0501 (9)	0.0548 (10)	−0.0025 (10)	0.0011 (10)	−0.0039 (8)
C3	0.0549 (10)	0.0489 (9)	0.0601 (10)	−0.0072 (9)	−0.0002 (10)	0.0062 (8)
C8	0.0717 (14)	0.0724 (13)	0.0616 (12)	−0.0123 (11)	0.0099 (11)	−0.0150 (10)

N1—C7	1.263 (2)	C7—H8A	0.9300
N1—C1	1.426 (2)	C5—C8	1.513 (3)
F1—C13	1.361 (2)	C15—C14	1.386 (3)
C6—C1	1.390 (3)	C15—H10A	0.9300
C6—C5	1.392 (2)	C2—C3	1.383 (3)
C6—H3A	0.9300	C2—H11A	0.9300
C1—C2	1.386 (2)	C14—C13	1.364 (3)
C10—C15	1.387 (3)	C14—H12A	0.9300
C10—C11	1.392 (3)	C9—H13A	0.9600
C10—C7	1.469 (2)	C9—H13B	0.9600
C4—C3	1.387 (3)	C9—H13C	0.9600
C4—C5	1.395 (2)	C11—H15A	0.9300
C4—C9	1.508 (2)	C3—H16A	0.9300
C12—C13	1.375 (3)	C8—H17A	0.9600
C12—C11	1.385 (3)	C8—H17B	0.9600
C12—H7A	0.9300	C8—H17C	0.9600

C7—N1—C1	118.46 (16)	C3—C2—H11A	120.2
C1—C6—C5	121.56 (16)	C1—C2—H11A	120.2
C1—C6—H3A	119.2	C13—C14—C15	117.8 (2)
C5—C6—H3A	119.2	C13—C14—H12A	121.1
C2—C1—C6	118.92 (17)	C15—C14—H12A	121.1
C2—C1—N1	122.44 (16)	C4—C9—H13A	109.5
C6—C1—N1	118.60 (16)	C4—C9—H13B	109.5
C15—C10—C11	118.99 (18)	H13A—C9—H13B	109.5
C15—C10—C7	119.64 (18)	C4—C9—H13C	109.5
C11—C10—C7	121.33 (17)	H13A—C9—H13C	109.5
C3—C4—C5	118.67 (16)	H13B—C9—H13C	109.5
C3—C4—C9	119.82 (17)	F1—C13—C14	118.3 (2)
C5—C4—C9	121.51 (17)	F1—C13—C12	118.2 (2)
C13—C12—C11	118.1 (2)	C14—C13—C12	123.44 (19)
C13—C12—H7A	121.0	C12—C11—C10	120.55 (19)
C11—C12—H7A	121.0	C12—C11—H15A	119.7
N1—C7—C10	123.40 (17)	C10—C11—H15A	119.7
N1—C7—H8A	118.3	C2—C3—C4	121.94 (17)
C10—C7—H8A	118.3	C2—C3—H16A	119.0
C6—C5—C4	119.28 (16)	C4—C3—H16A	119.0
C6—C5—C8	119.61 (17)	C5—C8—H17A	109.5
C4—C5—C8	121.11 (17)	C5—C8—H17B	109.5
C14—C15—C10	121.2 (2)	H17A—C8—H17B	109.5
C14—C15—H10A	119.4	C5—C8—H17C	109.5
C10—C15—H10A	119.4	H17A—C8—H17C	109.5
C3—C2—C1	119.62 (17)	H17B—C8—H17C	109.5

3 in total

1 in total

1. Crystal structure of 4-chloro-2-{(E)-[(3,4-di-methyl-phen-yl)imino]-meth-yl}phenol.

Authors: Muhammad Salim; Muhammad Nawaz Tahir; Munawar Ali Munawar; Muhammad Shahid; Hazoor Ahmad Shad
Journal: Acta Crystallogr E Crystallogr Commun Date: 2015-05-23