Literature DB >> 23723797

N-[(E)-4-Bromo-benzyl-idene]-2,3-di-methyl-aniline.

Li-Xia Sun¹, Ling-Zhi Zhu, Jun-Kai Wang.

Abstract

The title compound, C15H14BrN, has an E conformation about the C=N bond and the dihedral angle between the benzene rings is 50.7 (2)°. In the crystal, mol-ecules are linked via C-H⋯π inter-actions, forming columns propagating along [010].

Entities: Chemical Disease Gene

Year: 2013 PMID： 23723797 PMCID： PMC3647831 DOI： 10.1107/S1600536813008088

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

Related literature

Schiff base derivativies have many pharmaceutical activities. For their antifungal effects, see: Aziz et al. (2010 ▶), for their radical scavenging activity, see: Lu et al. (2012 ▶), for their inhibition of enzyme activity, see: Schmidt et al. (2009 ▶) and for their antibacterial activity, see: Shi et al. (2010 ▶). For related structures, see: Sun et al. (2011a ▶,b ▶); Guo et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14BrN M = 288.18 Monoclinic, a = 12.945 (9) Å b = 7.857 (5) Å c = 14.497 (10) Å β = 113.384 (8)° V = 1353.3 (16) Å3 Z = 4 Mo Kα radiation μ = 3.02 mm−1 T = 296 K 0.25 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.519, T max = 0.598 5865 measured reflections 2525 independent reflections 1154 reflections with I > 2σ(I) R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.112 S = 0.94 2525 reflections 157 parameters H-atom parameters constrained Δρmax = 0.35 e Å−3 Δρmin = −0.25 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; 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: SHELXTL. Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813008088/su2578sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813008088/su2578Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536813008088/su2578Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄BrN	F(000) = 584
M_r = 288.18	D_x = 1.414 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2505 reflections
a = 12.945 (9) Å	θ = 2.7–25.5°
b = 7.857 (5) Å	µ = 3.02 mm⁻¹
c = 14.497 (10) Å	T = 296 K
β = 113.384 (8)°	Block, yellow
V = 1353.3 (16) Å³	0.25 × 0.20 × 0.19 mm
Z = 4

Bruker APEXII CCD diffractometer	2525 independent reflections
Radiation source: fine-focus sealed tube	1154 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.058
φ and ω scans	θ_max = 25.5°, θ_min = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→10
T_min = 0.519, T_max = 0.598	k = −9→7
5865 measured reflections	l = −15→17

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0477P)²] where P = (F_o² + 2F_c²)/3
S = 0.94	(Δ/σ)_max < 0.001
2525 reflections	Δρ_max = 0.35 e Å⁻³
157 parameters	Δρ_min = −0.25 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0298 (19)

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
Br1	0.07853 (5)	0.88838 (7)	0.11686 (4)	0.0919 (4)
C1	0.0611 (4)	0.8732 (5)	0.3942 (3)	0.0581 (13)
H1	0.0091	0.9056	0.4205	0.070*
C2	0.0362 (4)	0.8999 (5)	0.2939 (3)	0.0643 (13)
H2	−0.0315	0.9504	0.2529	0.077*
C3	0.1122 (5)	0.8513 (5)	0.2554 (3)	0.0547 (12)
C4	0.2111 (4)	0.7767 (7)	0.3137 (4)	0.0736 (15)
H4	0.2616	0.7431	0.2860	0.088*
C5	0.2363 (4)	0.7508 (6)	0.4154 (3)	0.0682 (15)
H5	0.3042	0.7002	0.4557	0.082*
C6	0.1617 (4)	0.7992 (5)	0.4572 (3)	0.0477 (11)
C7	0.1882 (4)	0.7675 (5)	0.5637 (3)	0.0513 (12)
H7	0.2592	0.7258	0.6036	0.062*
C8	0.1554 (4)	0.7691 (5)	0.7095 (3)	0.0434 (11)
C9	0.2578 (4)	0.8290 (6)	0.7761 (3)	0.0582 (13)
H9	0.3060	0.8842	0.7525	0.070*
C10	0.2887 (4)	0.8071 (7)	0.8781 (3)	0.0713 (14)
H10	0.3586	0.8452	0.9231	0.086*
C11	0.2169 (4)	0.7295 (6)	0.9130 (3)	0.0602 (13)
H11	0.2382	0.7163	0.9818	0.072*
C12	0.1130 (4)	0.6702 (5)	0.8474 (3)	0.0500 (12)
C13	0.0802 (3)	0.6918 (5)	0.7437 (3)	0.0449 (11)
C14	0.0371 (4)	0.5812 (6)	0.8890 (4)	0.0776 (16)
H14A	0.0750	0.5718	0.9607	0.116*
H14B	0.0191	0.4695	0.8602	0.116*
H14C	−0.0309	0.6457	0.8726	0.116*
C15	−0.0326 (4)	0.6292 (6)	0.6700 (3)	0.0758 (15)
H15A	−0.0869	0.6384	0.6995	0.114*
H15B	−0.0262	0.5124	0.6535	0.114*
H15C	−0.0564	0.6970	0.6100	0.114*
N1	0.1199 (3)	0.7938 (4)	0.6039 (2)	0.0501 (9)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.1350 (6)	0.0914 (5)	0.0529 (3)	−0.0264 (4)	0.0410 (3)	0.0038 (3)
C1	0.064 (3)	0.061 (3)	0.052 (3)	0.015 (3)	0.025 (3)	0.005 (2)
C2	0.075 (4)	0.054 (3)	0.061 (3)	0.021 (3)	0.024 (3)	0.008 (3)
C3	0.069 (3)	0.050 (3)	0.044 (2)	−0.006 (3)	0.023 (3)	0.005 (2)
C4	0.069 (4)	0.104 (4)	0.061 (3)	−0.012 (3)	0.039 (3)	−0.015 (3)
C5	0.051 (3)	0.095 (4)	0.060 (3)	0.013 (3)	0.024 (3)	0.000 (3)
C6	0.051 (3)	0.047 (3)	0.048 (3)	−0.001 (2)	0.023 (2)	−0.001 (2)
C7	0.058 (3)	0.047 (3)	0.050 (3)	0.002 (2)	0.022 (3)	0.000 (2)
C8	0.047 (3)	0.034 (3)	0.049 (3)	0.004 (2)	0.018 (2)	0.001 (2)
C9	0.062 (3)	0.055 (3)	0.063 (3)	−0.015 (3)	0.030 (3)	−0.005 (2)
C10	0.065 (3)	0.089 (4)	0.057 (3)	−0.024 (3)	0.021 (3)	−0.020 (3)
C11	0.072 (4)	0.066 (4)	0.044 (3)	−0.004 (3)	0.024 (3)	−0.002 (2)
C12	0.062 (3)	0.043 (3)	0.053 (3)	0.002 (2)	0.032 (3)	0.003 (2)
C13	0.051 (3)	0.037 (3)	0.046 (2)	0.002 (2)	0.018 (2)	−0.005 (2)
C14	0.093 (4)	0.080 (4)	0.070 (3)	−0.008 (3)	0.042 (3)	0.009 (3)
C15	0.059 (3)	0.100 (4)	0.062 (3)	−0.015 (3)	0.018 (3)	−0.005 (3)
N1	0.061 (2)	0.048 (2)	0.048 (2)	0.004 (2)	0.028 (2)	0.0032 (17)

Br1—C3	1.901 (4)	C8—N1	1.426 (5)
C1—C2	1.375 (6)	C9—C10	1.380 (6)
C1—C6	1.387 (5)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.366 (6)
C2—C3	1.365 (6)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.383 (6)
C3—C4	1.355 (6)	C11—H11	0.9300
C4—C5	1.393 (6)	C12—C13	1.401 (5)
C4—H4	0.9300	C12—C14	1.513 (6)
C5—C6	1.382 (5)	C13—C15	1.509 (6)
C5—H5	0.9300	C14—H14A	0.9600
C6—C7	1.464 (5)	C14—H14B	0.9600
C7—N1	1.253 (5)	C14—H14C	0.9600
C7—H7	0.9300	C15—H15A	0.9600
C8—C9	1.377 (5)	C15—H15B	0.9600
C8—C13	1.395 (5)	C15—H15C	0.9600

C2—C1—C6	121.6 (4)	C10—C9—H9	120.1
C2—C1—H1	119.2	C11—C10—C9	120.1 (4)
C6—C1—H1	119.2	C11—C10—H10	120.0
C3—C2—C1	119.1 (4)	C9—C10—H10	120.0
C3—C2—H2	120.5	C10—C11—C12	121.0 (4)
C1—C2—H2	120.5	C10—C11—H11	119.5
C4—C3—C2	121.5 (4)	C12—C11—H11	119.5
C4—C3—Br1	119.2 (4)	C11—C12—C13	119.6 (4)
C2—C3—Br1	119.3 (4)	C11—C12—C14	119.3 (4)
C3—C4—C5	119.3 (4)	C13—C12—C14	121.0 (4)
C3—C4—H4	120.4	C8—C13—C12	118.5 (4)
C5—C4—H4	120.4	C8—C13—C15	120.3 (4)
C6—C5—C4	120.9 (4)	C12—C13—C15	121.1 (4)
C6—C5—H5	119.6	C12—C14—H14A	109.5
C4—C5—H5	119.6	C12—C14—H14B	109.5
C5—C6—C1	117.7 (4)	H14A—C14—H14B	109.5
C5—C6—C7	120.2 (4)	C12—C14—H14C	109.5
C1—C6—C7	122.1 (4)	H14A—C14—H14C	109.5
N1—C7—C6	123.3 (4)	H14B—C14—H14C	109.5
N1—C7—H7	118.4	C13—C15—H15A	109.5
C6—C7—H7	118.4	C13—C15—H15B	109.5
C9—C8—C13	120.8 (4)	H15A—C15—H15B	109.5
C9—C8—N1	121.1 (4)	C13—C15—H15C	109.5
C13—C8—N1	117.9 (4)	H15A—C15—H15C	109.5
C8—C9—C10	119.9 (4)	H15B—C15—H15C	109.5
C8—C9—H9	120.1	C7—N1—C8	119.4 (4)

C6—C1—C2—C3	0.4 (7)	C9—C10—C11—C12	0.6 (8)
C1—C2—C3—C4	0.4 (7)	C10—C11—C12—C13	−0.8 (7)
C1—C2—C3—Br1	−179.8 (3)	C10—C11—C12—C14	178.5 (4)
C2—C3—C4—C5	−0.7 (7)	C9—C8—C13—C12	−2.6 (6)
Br1—C3—C4—C5	179.5 (4)	N1—C8—C13—C12	−178.6 (4)
C3—C4—C5—C6	0.3 (7)	C9—C8—C13—C15	179.0 (4)
C4—C5—C6—C1	0.4 (7)	N1—C8—C13—C15	3.0 (6)
C4—C5—C6—C7	178.6 (4)	C11—C12—C13—C8	1.7 (6)
C2—C1—C6—C5	−0.8 (7)	C14—C12—C13—C8	−177.6 (4)
C2—C1—C6—C7	−178.9 (4)	C11—C12—C13—C15	−179.9 (4)
C5—C6—C7—N1	−173.1 (4)	C14—C12—C13—C15	0.9 (6)
C1—C6—C7—N1	4.9 (7)	C6—C7—N1—C8	−176.2 (4)
C13—C8—C9—C10	2.5 (6)	C9—C8—N1—C7	44.6 (6)
N1—C8—C9—C10	178.4 (4)	C13—C8—N1—C7	−139.3 (4)
C8—C9—C10—C11	−1.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cg2ⁱ	0.93	2.99	3.830 (6)	151
C15—H15B···Cg1ⁱⁱ	0.96	2.99	3.781 (6)	140

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8–C13 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯Cg2ⁱ	0.93	2.99	3.830 (6)	151
C15—H15B⋯Cg1ⁱⁱ	0.96	2.99	3.781 (6)	140

Symmetry codes: (i) ; (ii) .

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