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

The title compound, C(16)H(16)BrNO(3), adopts an E configuration with respect to the imine C=N bond. The two benzene rings are twisted with respect to each other at an angle of 38.3 (1)°. In the crystal structure, mol-ecules are connected by weak bifurcated C-H⋯(O, O) hydrogen bonds, forming a helical chain along the b axis.

Related literature

The structure of the isotypic 4-chloro compound was reported by Khalaji et al. (2009 ▶). For structures containing a 4-bromo­aniline unit, see: Khalaji et al. (2007 ▶); Khalaji & Harrison (2008 ▶).

Experimental

Crystal data

C16H16BrNO3

M = 350.21

Monoclinic,

a = 7.1951 (4) Å

b = 8.3722 (5) Å

c = 13.2882 (8) Å

β = 104.413 (3)°

V = 775.27 (8) Å3

Z = 2

Mo Kα radiation

μ = 2.66 mm−1

T = 296 (2) K

0.40 × 0.30 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (; Bruker, 2006 ▶) T min = 0.403, T max = 0.671

18229 measured reflections

3497 independent reflections

3064 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.065

S = 1.09

3497 reflections

193 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.53 e Å−3

Absolute structure: Flack (1983 ▶), 1511 Friedel pairs

Flack parameter: 0.012 (6)

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809003432/wn2308sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003432/wn2308Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C16H16BrNO3	F(000) = 356
Mr = 350.21	Dx = 1.500 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 9957 reflections
a = 7.1951 (4) Å	θ = 2.9–29.0°
b = 8.3722 (5) Å	µ = 2.66 mm−1
c = 13.2882 (8) Å	T = 296 K
β = 104.413 (3)°	Block, colourless
V = 775.27 (8) Å3	0.40 × 0.30 × 0.15 mm
Z = 2

Bruker APEXII CCD diffractometer	3497 independent reflections
Radiation source: fine-focus sealed tube	3064 reflections with I > 2σ(I)
graphite	Rint = 0.023
ω scans	θmax = 28.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
Tmin = 0.403, Tmax = 0.671	k = −10→10
18229 measured reflections	l = −17→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)] = 0.025	H-atom parameters constrained
wR(F2) = 0.065	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.0173P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.002
3497 reflections	Δρmax = 0.30 e Å−3
193 parameters	Δρmin = −0.53 e Å−3
1 restraint	Absolute structure: Flack (1983), 1511 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.012 (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	Uiso*/Ueq
Br1	0.99402 (3)	0.96811 (5)	0.988948 (16)	0.06694 (9)
O1	−0.26888 (18)	0.4772 (2)	0.36904 (9)	0.0522 (3)
O2	−0.46171 (19)	0.29368 (19)	0.46988 (11)	0.0498 (3)
O3	−0.3668 (2)	0.2687 (2)	0.67538 (12)	0.0600 (4)
N1	0.2656 (2)	0.6014 (2)	0.79047 (14)	0.0502 (4)
C1	0.7715 (3)	0.8470 (2)	0.92769 (15)	0.0450 (4)
C2	0.6245 (3)	0.8386 (3)	0.97682 (18)	0.0595 (6)
H2	0.6355	0.8891	1.0404	0.071*
C3	0.4614 (4)	0.7546 (3)	0.9308 (2)	0.0604 (6)
H3	0.3634	0.7458	0.9648	0.072*
C4	0.4402 (3)	0.6827 (2)	0.83465 (15)	0.0436 (4)
C5	0.5939 (3)	0.6886 (3)	0.78856 (16)	0.0478 (5)
H5	0.5850	0.6368	0.7256	0.057*
C6	0.7594 (3)	0.7705 (3)	0.83532 (17)	0.0498 (5)
H6	0.8618	0.7736	0.8043	0.060*
C7	0.2013 (3)	0.6071 (2)	0.69260 (16)	0.0427 (4)
H7	0.2700	0.6651	0.6542	0.051*
C8	0.0246 (3)	0.5272 (2)	0.63686 (16)	0.0411 (4)
C9	−0.0833 (3)	0.4364 (2)	0.69019 (15)	0.0432 (5)
H9	−0.0454	0.4266	0.7621	0.052*
C10	−0.2484 (3)	0.3611 (2)	0.63335 (16)	0.0430 (4)
C11	−0.3059 (3)	0.3758 (2)	0.52599 (16)	0.0411 (4)
C12	−0.1991 (2)	0.4695 (3)	0.47377 (12)	0.0403 (3)
C13	−0.0336 (3)	0.5450 (2)	0.53043 (16)	0.0417 (4)
H13	0.0381	0.6078	0.4963	0.050*
C14	−0.1666 (4)	0.5679 (4)	0.3108 (2)	0.0785 (8)
H14A	−0.1641	0.6779	0.3316	0.118*
H14B	−0.2287	0.5591	0.2382	0.118*
H14C	−0.0377	0.5284	0.3232	0.118*
C15	−0.6378 (3)	0.3769 (4)	0.4588 (2)	0.0673 (7)
H15A	−0.6588	0.3972	0.5262	0.101*
H15B	−0.7412	0.3133	0.4189	0.101*
H15C	−0.6324	0.4765	0.4238	0.101*
C16	−0.3111 (5)	0.2366 (4)	0.7828 (2)	0.0761 (8)
H16A	−0.1813	0.1983	0.8010	0.114*
H16B	−0.3944	0.1569	0.7997	0.114*
H16C	−0.3198	0.3327	0.8208	0.114*

	U11	U22	U33	U12	U13	U23
Br1	0.05738 (13)	0.06441 (15)	0.06520 (14)	−0.01188 (12)	−0.01083 (9)	−0.00513 (15)
O1	0.0556 (7)	0.0567 (8)	0.0431 (6)	−0.0113 (9)	0.0100 (5)	−0.0013 (9)
O2	0.0463 (7)	0.0467 (8)	0.0547 (8)	−0.0096 (7)	0.0092 (6)	−0.0106 (7)
O3	0.0588 (9)	0.0704 (10)	0.0506 (9)	−0.0236 (7)	0.0135 (7)	0.0033 (7)
N1	0.0478 (9)	0.0533 (10)	0.0498 (11)	−0.0107 (8)	0.0126 (8)	−0.0056 (8)
C1	0.0423 (9)	0.0395 (11)	0.0456 (11)	−0.0019 (8)	−0.0036 (8)	−0.0007 (8)
C2	0.0630 (13)	0.0664 (15)	0.0468 (12)	−0.0018 (11)	0.0094 (10)	−0.0168 (10)
C3	0.0582 (13)	0.0769 (18)	0.0500 (14)	−0.0086 (11)	0.0208 (11)	−0.0114 (10)
C4	0.0425 (9)	0.0441 (12)	0.0418 (10)	−0.0030 (9)	0.0060 (8)	−0.0009 (8)
C5	0.0463 (10)	0.0538 (14)	0.0400 (11)	−0.0014 (10)	0.0044 (8)	−0.0099 (9)
C6	0.0408 (10)	0.0595 (14)	0.0466 (12)	−0.0002 (9)	0.0060 (9)	−0.0020 (10)
C7	0.0376 (9)	0.0393 (10)	0.0504 (12)	−0.0019 (8)	0.0095 (8)	−0.0013 (8)
C8	0.0355 (9)	0.0337 (9)	0.0524 (11)	0.0014 (7)	0.0076 (8)	−0.0044 (7)
C9	0.0418 (9)	0.0433 (13)	0.0442 (9)	−0.0024 (7)	0.0101 (7)	−0.0026 (7)
C10	0.0434 (10)	0.0377 (11)	0.0497 (11)	−0.0038 (8)	0.0148 (8)	−0.0041 (8)
C11	0.0378 (9)	0.0345 (10)	0.0503 (11)	−0.0006 (8)	0.0097 (8)	−0.0080 (8)
C12	0.0412 (8)	0.0356 (8)	0.0449 (8)	0.0025 (11)	0.0122 (6)	−0.0028 (11)
C13	0.0397 (9)	0.0371 (10)	0.0502 (11)	−0.0020 (7)	0.0148 (8)	−0.0011 (8)
C14	0.0817 (17)	0.102 (2)	0.0505 (14)	−0.0239 (16)	0.0142 (13)	0.0169 (14)
C15	0.0429 (11)	0.0708 (17)	0.0828 (18)	−0.0044 (12)	0.0056 (11)	−0.0027 (13)
C16	0.0790 (17)	0.086 (2)	0.0611 (18)	−0.0228 (16)	0.0134 (15)	0.0180 (13)

Br1—C1	1.8992 (19)	C7—C8	1.464 (3)
O1—C12	1.358 (2)	C7—H7	0.9300
O1—C14	1.414 (3)	C8—C9	1.399 (3)
O2—C11	1.367 (2)	C8—C13	1.379 (3)
O2—C15	1.421 (3)	C9—H9	0.9300
O3—C16	1.409 (3)	C10—C9	1.390 (3)
O3—C10	1.368 (2)	C11—C10	1.388 (3)
C1—C2	1.376 (3)	C12—C13	1.392 (3)
C1—C6	1.368 (3)	C12—C11	1.397 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C2	1.375 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—N1	1.421 (2)	C14—H14C	0.9600
C4—C3	1.386 (3)	C15—H15A	0.9600
C4—C5	1.392 (3)	C15—H15B	0.9600
C5—C6	1.380 (3)	C15—H15C	0.9600
C5—H5	0.9300	C16—H16A	0.9600
C6—H6	0.9300	C16—H16B	0.9600
C7—N1	1.268 (3)	C16—H16C	0.9600
O1—C12—C11	115.25 (16)	C6—C1—Br1	119.56 (16)
O1—C12—C13	125.52 (17)	C6—C1—C2	121.14 (18)
O1—C14—H14A	109.5	C6—C5—C4	120.69 (19)
O1—C14—H14B	109.5	C6—C5—H5	119.7
O1—C14—H14C	109.5	C7—N1—C4	117.70 (17)
O2—C11—C10	120.65 (17)	C8—C7—H7	118.3
O2—C11—C12	119.28 (17)	C8—C9—H9	120.7
O2—C15—H15A	109.5	C8—C13—C12	120.43 (18)
O2—C15—H15B	109.5	C8—C13—H13	119.8
O2—C15—H15C	109.5	C9—C8—C7	120.90 (18)
O3—C10—C9	124.70 (18)	C10—O3—C16	118.18 (19)
O3—C10—C11	114.39 (17)	C10—C9—C8	118.58 (18)
O3—C16—H16A	109.5	C10—C9—H9	120.7
O3—C16—H16B	109.5	C10—C11—C12	120.00 (17)
O3—C16—H16C	109.5	C11—O2—C15	113.49 (18)
N1—C7—C8	123.41 (18)	C11—C10—C9	120.91 (17)
N1—C7—H7	118.3	C12—O1—C14	118.41 (17)
C1—C2—H2	120.4	C13—C8—C9	120.83 (17)
C1—C6—C5	119.45 (19)	C13—C8—C7	118.27 (17)
C1—C6—H6	120.3	C13—C12—C11	119.23 (16)
C2—C1—Br1	119.30 (15)	C12—C13—H13	119.8
C2—C3—C4	121.2 (2)	H14A—C14—H14B	109.5
C2—C3—H3	119.4	H14A—C14—H14C	109.5
C3—C2—C1	119.1 (2)	H14B—C14—H14C	109.5
C3—C2—H2	120.4	H15A—C15—H15B	109.5
C3—C4—N1	118.17 (18)	H15A—C15—H15C	109.5
C3—C4—C5	118.22 (19)	H15B—C15—H15C	109.5
C4—C3—H3	119.4	H16A—C16—H16B	109.5
C4—C5—H5	119.7	H16A—C16—H16C	109.5
C5—C4—N1	123.56 (17)	H16B—C16—H16C	109.5
C5—C6—H6	120.3
Br1—C1—C2—C3	178.2 (2)	C6—C1—C2—C3	−1.4 (4)
Br1—C1—C6—C5	−177.04 (17)	C7—C8—C9—C10	−179.05 (17)
O1—C12—C11—O2	3.6 (3)	C7—C8—C13—C12	179.05 (18)
O1—C12—C11—C10	−179.35 (19)	C8—C7—N1—C4	179.19 (18)
O1—C12—C13—C8	−179.36 (19)	C9—C10—O3—C16	−5.2 (3)
O2—C11—C10—O3	−4.2 (3)	C9—C8—C13—C12	−1.5 (3)
O2—C11—C10—C9	175.96 (17)	C11—C10—O3—C16	174.9 (2)
O3—C10—C9—C8	179.93 (18)	C11—C12—C13—C8	0.2 (3)
N1—C4—C3—C2	−178.3 (2)	C11—C10—C9—C8	−0.2 (3)
N1—C4—C5—C6	179.6 (2)	C12—C11—C10—O3	178.83 (19)
N1—C7—C8—C13	178.51 (19)	C12—C11—C10—C9	−1.0 (3)
N1—C7—C8—C9	−0.9 (3)	C13—C8—C9—C10	1.5 (3)
C2—C1—C6—C5	2.6 (3)	C13—C12—C11—O2	−175.99 (19)
C3—C4—N1—C7	144.8 (2)	C13—C12—C11—C10	1.0 (3)
C3—C4—C5—C6	−3.0 (3)	C14—O1—C12—C11	−179.1 (2)
C4—C3—C2—C1	−2.0 (4)	C14—O1—C12—C13	0.5 (3)
C4—C5—C6—C1	−0.3 (4)	C15—O2—C11—C10	88.3 (2)
C5—C4—C3—C2	4.2 (4)	C15—O2—C11—C12	−94.7 (2)
C5—C4—N1—C7	−37.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1i	0.93	2.63	3.272 (2)	127
C7—H7···O2i	0.93	2.63	3.553 (3)	172

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1i	0.93	2.63	3.272 (2)	127
C7—H7⋯O2i	0.93	2.63	3.553 (3)	172

Symmetry code: (i) .