Literature DB >> 21588588

(E)-4-Bromo-N-(2,3-dimeth-oxy-benzyl-idene)aniline.

Karla Fejfarová, Emanuel Makrlík, Aliakbar Dehno Khalaji.

Abstract

The title Schiff base compound, C(15)H(14)BrNO(2), was prepared by the condensation of 2,3-dimeth-oxy-benzaldehyde with 4-bromo-aniline. It adopts an E configuration with respect to the C=N bond. The dihedral angle between the two aromatic rings is 56.79 (8)°. Weak C-H⋯O and C--H⋯π bonds can be found in the crystal structure.

Entities: Chemical Disease Species

Year: 2010 PMID： 21588588 PMCID： PMC3007893 DOI： 10.1107/S1600536810029880

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

Related literature

For applications of Schiff-base compounds, see: Yildiz et al. (2008 ▶); Hijji et al. (2009 ▶); Karakas et al. (2008 ▶). For related structures, see: Khalaji et al. (2007 ▶, 2009 ▶); Khalaji & Harrison (2008 ▶); Khalaji & Simpson (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H14BrNO2 M = 320.2 Orthorhombic, a = 13.9978 (2) Å b = 7.0557 (1) Å c = 27.3758 (4) Å V = 2703.75 (7) Å3 Z = 8 Cu Kα radiation μ = 4.13 mm−1 T = 120 K 0.55 × 0.33 × 0.23 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.365, T max = 0.698 24799 measured reflections 2365 independent reflections 2178 reflections with I > 3σ(I) R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.030 wR(F 2) = 0.123 S = 1.82 2365 reflections 172 parameters H-atom parameters constrained Δρmax = 0.28 e Å−3 Δρmin = −0.31 e Å−3 Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: JANA2006 (Petříček et al., 2006 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: JANA2006. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029880/bt5308sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029880/bt5308Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄BrNO₂	F(000) = 1296
M_r = 320.2	D_x = 1.573 Mg m⁻³
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17724 reflections
a = 13.9978 (2) Å	θ = 3.2–66.7°
b = 7.0557 (1) Å	µ = 4.13 mm⁻¹
c = 27.3758 (4) Å	T = 120 K
V = 2703.75 (7) Å³	Prism, colourless
Z = 8	0.55 × 0.33 × 0.23 mm

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	2365 independent reflections
Radiation source: X-ray tube	2178 reflections with I > 3σ(I)
mirror	R_int = 0.041
Detector resolution: 10.3784 pixels mm^-1	θ_max = 66.8°, θ_min = 4.5°
Rotation method data acquisition using ω scans	h = −16→16
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −8→8
T_min = 0.365, T_max = 0.698	l = −32→32
24799 measured reflections

Refinement on F²	56 constraints
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.123	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0035999999I²]
S = 1.82	(Δ/σ)_max = 0.004
2365 reflections	Δρ_max = 0.28 e Å⁻³
172 parameters	Δρ_min = −0.31 e Å⁻³
0 restraints

Experimental. CrysAlisPro, Oxford Diffraction (2009), Analytical numeric absorption correction using a multifaceted crystal model.

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.

	x	y	z	U_iso*/U_eq
Br1	0.301516 (18)	0.35856 (4)	0.297810 (9)	0.03286 (15)
O1	0.46379 (10)	0.9683 (2)	0.56018 (5)	0.0238 (5)
O2	0.48573 (11)	1.0730 (2)	0.65342 (6)	0.0293 (5)
N1	0.30118 (11)	0.5268 (3)	0.51592 (7)	0.0204 (6)
C1	0.35592 (14)	0.6587 (3)	0.53157 (8)	0.0212 (6)
C2	0.36519 (14)	0.7060 (3)	0.58364 (8)	0.0210 (6)
C3	0.41859 (14)	0.8666 (3)	0.59624 (8)	0.0208 (6)
C4	0.42987 (14)	0.9178 (3)	0.64562 (8)	0.0245 (7)
C5	0.38574 (16)	0.8110 (4)	0.68186 (8)	0.0278 (7)
C6	0.33284 (18)	0.6502 (3)	0.66869 (9)	0.0285 (7)
C7	0.32263 (16)	0.5970 (3)	0.62059 (9)	0.0248 (7)
C8	0.42620 (16)	1.1557 (3)	0.55295 (9)	0.0279 (7)
C9	0.5018 (3)	1.1323 (5)	0.70222 (9)	0.0479 (11)
C10	0.30271 (13)	0.4922 (3)	0.46499 (9)	0.0217 (7)
C11	0.21645 (16)	0.4759 (3)	0.43955 (8)	0.0215 (7)
C12	0.21516 (16)	0.4411 (3)	0.38997 (9)	0.0239 (7)
C13	0.30115 (14)	0.4180 (4)	0.36557 (9)	0.0235 (7)
C14	0.38827 (15)	0.4325 (3)	0.38971 (8)	0.0248 (7)
C15	0.38811 (15)	0.4684 (3)	0.43928 (8)	0.0228 (7)
H1	0.392541	0.729923	0.50828	0.0255*
H5	0.391454	0.846917	0.715555	0.0334*
H6	0.30309	0.575572	0.693754	0.0342*
H7	0.286533	0.485819	0.612357	0.0298*
H8a	0.445019	1.201521	0.521356	0.0419*
H8b	0.357749	1.152148	0.554914	0.0419*
H8c	0.450723	1.238776	0.577735	0.0419*
H9a	0.553271	1.222056	0.702951	0.0718*
H9b	0.444871	1.190439	0.714812	0.0718*
H9c	0.518004	1.024448	0.721929	0.0718*
H11	0.157197	0.489141	0.456874	0.0259*
H12	0.155673	0.433057	0.37264	0.0287*
H14	0.447304	0.417836	0.372267	0.0298*
H15	0.447782	0.477042	0.45641	0.0273*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0370 (3)	0.0382 (3)	0.0233 (3)	0.00213 (10)	0.00027 (8)	−0.00306 (9)
O1	0.0186 (7)	0.0251 (8)	0.0277 (8)	−0.0003 (6)	0.0057 (6)	−0.0002 (6)
O2	0.0230 (8)	0.0386 (10)	0.0263 (8)	−0.0067 (7)	0.0009 (6)	−0.0076 (7)
N1	0.0158 (9)	0.0199 (10)	0.0256 (11)	0.0023 (6)	−0.0014 (6)	−0.0015 (8)
C1	0.0139 (10)	0.0246 (12)	0.0252 (11)	0.0035 (8)	0.0010 (8)	0.0020 (8)
C2	0.0135 (9)	0.0233 (11)	0.0261 (11)	0.0043 (8)	−0.0008 (8)	0.0001 (9)
C3	0.0135 (9)	0.0245 (12)	0.0243 (11)	0.0041 (8)	0.0011 (8)	0.0004 (8)
C4	0.0165 (10)	0.0283 (12)	0.0289 (12)	0.0034 (9)	−0.0012 (9)	−0.0024 (9)
C5	0.0233 (11)	0.0359 (13)	0.0242 (12)	0.0024 (10)	−0.0008 (9)	−0.0027 (10)
C6	0.0251 (11)	0.0347 (14)	0.0259 (13)	0.0005 (9)	0.0025 (10)	0.0057 (9)
C7	0.0187 (9)	0.0256 (12)	0.0302 (13)	0.0007 (9)	−0.0009 (9)	0.0017 (10)
C8	0.0245 (11)	0.0276 (13)	0.0316 (13)	−0.0026 (9)	0.0002 (10)	0.0026 (9)
C9	0.0532 (19)	0.061 (2)	0.0292 (16)	−0.0202 (15)	0.0065 (11)	−0.0175 (11)
C10	0.0199 (11)	0.0188 (12)	0.0265 (13)	−0.0005 (8)	−0.0002 (7)	0.0029 (9)
C11	0.0160 (10)	0.0212 (12)	0.0274 (13)	0.0005 (8)	0.0003 (8)	0.0024 (9)
C12	0.0187 (10)	0.0238 (13)	0.0291 (13)	−0.0022 (9)	−0.0054 (9)	0.0012 (9)
C13	0.0258 (12)	0.0222 (12)	0.0225 (12)	0.0004 (8)	−0.0002 (8)	0.0043 (9)
C14	0.0182 (11)	0.0266 (13)	0.0296 (12)	0.0041 (9)	0.0043 (9)	0.0012 (9)
C15	0.0159 (10)	0.0222 (12)	0.0302 (12)	0.0001 (8)	−0.0028 (8)	0.0011 (9)

Br1—C13	1.902 (2)	C7—H7	0.96
O1—C3	1.375 (3)	C8—H8a	0.96
O1—C8	1.437 (3)	C8—H8b	0.96
O2—C4	1.362 (3)	C8—H8c	0.96
O2—C9	1.418 (3)	C9—H9a	0.96
N1—C1	1.279 (3)	C9—H9b	0.96
N1—C10	1.416 (3)	C9—H9c	0.96
C1—C2	1.470 (3)	C10—C11	1.399 (3)
C1—H1	0.96	C10—C15	1.397 (3)
C2—C3	1.401 (3)	C11—C12	1.380 (3)
C2—C7	1.403 (3)	C11—H11	0.96
C3—C4	1.408 (3)	C12—C13	1.386 (3)
C4—C5	1.391 (3)	C12—H12	0.96
C5—C6	1.402 (3)	C13—C14	1.391 (3)
C5—H5	0.96	C14—C15	1.380 (3)
C6—C7	1.377 (3)	C14—H14	0.96
C6—H6	0.96	C15—H15	0.96

C3—O1—C8	114.26 (16)	H8a—C8—H8b	109.4709
C4—O2—C9	118.40 (19)	H8a—C8—H8c	109.4712
C1—N1—C10	116.48 (19)	H8b—C8—H8c	109.4719
N1—C1—C2	122.9 (2)	O2—C9—H9a	109.4702
N1—C1—H1	118.5696	O2—C9—H9b	109.4705
C2—C1—H1	118.5683	O2—C9—H9c	109.4702
C1—C2—C3	118.01 (19)	H9a—C9—H9b	109.4713
C1—C2—C7	122.51 (19)	H9a—C9—H9c	109.472
C3—C2—C7	119.5 (2)	H9b—C9—H9c	109.473
O1—C3—C2	119.40 (19)	N1—C10—C11	119.44 (18)
O1—C3—C4	120.25 (18)	N1—C10—C15	121.99 (18)
C2—C3—C4	120.3 (2)	C11—C10—C15	118.5 (2)
O2—C4—C3	114.91 (19)	C10—C11—C12	121.1 (2)
O2—C4—C5	125.4 (2)	C10—C11—H11	119.4722
C3—C4—C5	119.7 (2)	C12—C11—H11	119.4722
C4—C5—C6	119.3 (2)	C11—C12—C13	118.9 (2)
C4—C5—H5	120.337	C11—C12—H12	120.5379
C6—C5—H5	120.3378	C13—C12—H12	120.5366
C5—C6—C7	121.4 (2)	Br1—C13—C12	119.89 (16)
C5—C6—H6	119.2822	Br1—C13—C14	118.51 (16)
C7—C6—H6	119.2822	C12—C13—C14	121.6 (2)
C2—C7—C6	119.7 (2)	C13—C14—C15	118.6 (2)
C2—C7—H7	120.1302	C13—C14—H14	120.6854
C6—C7—H7	120.13	C15—C14—H14	120.6846
O1—C8—H8a	109.4703	C10—C15—C14	121.2 (2)
O1—C8—H8b	109.4718	C10—C15—H15	119.378
O1—C8—H8c	109.4712	C14—C15—H15	119.3768

C8—O1—C3—C2	113.2 (2)	C10—N1—C1—C2	−177.41 (18)
C8—O1—C3—C4	−70.0 (2)	C1—N1—C10—C11	−132.3 (2)
C9—O2—C4—C3	−179.1 (2)	C1—N1—C10—C15	49.5 (3)
C9—O2—C4—C5	0.5 (3)

Cg1 is the centroid of the dimethoxy-substituted aromatic ring.

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O2ⁱ	0.96	2.48	3.425 (3)	167
C7—H7···Cg1ⁱⁱ	0.96	2.84	3.680 (2)	147
C14—H14···Cg1ⁱⁱⁱ	0.96	2.77	3.618 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the dimethoxy-substituted aromatic ring C2–C7.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O2ⁱ	0.96	2.48	3.425 (3)	167
C7—H7⋯Cg1ⁱⁱ	0.96	2.84	3.680 (2)	147
C14—H14⋯Cg1ⁱⁱⁱ	0.96	2.77	3.618 (2)	147

Symmetry codes: (i) ; (ii) ; (iii) .

2 in total

1. (E)-4-Bromo-N-(2,4-dimethoxy-benzyl-idene)aniline.

Authors: Aliakbar D Khalaji; Jim Simpson
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-02-21

2. 4-Bromo-N-(3,4,5-trimethoxy-benzyl-idene)aniline.

Authors: Aliakbar Dehno Khalaji; Matthias Weil; Kazuma Gotoh; Hiroyuki Ishida
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-01-31

2 in total