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

The title Schiff base compound, C(16)H(16)BrNO(3), adopts an E configuration with respect to the C=N bond. The dihedral angle between the two aromatic rings is 64.02 (6)°.

Related literature

For applications of Schiff-base compounds, see: Yildiz et al. (2008 ▶); Hijji et al. (2009 ▶); Karakas et al. (2008 ▶); Hadjoudis et al. (2004 ▶). For related structures, see: Khalaji et al. (2007 ▶, 2008 ▶, 2009 ▶, 2010 ▶); Khalaji & Harrison (2008 ▶); Khalaji & Simpson (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C16H16BrNO3

M = 350.2

Triclinic,

a = 7.9103 (3) Å

b = 9.9902 (4) Å

c = 10.7821 (3) Å

α = 93.068 (3)°

β = 108.568 (3)°

γ = 109.679 (3)°

V = 748.10 (5) Å3

Z = 2

Cu Kα radiation

μ = 3.83 mm−1

T = 120 K

0.49 × 0.38 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini Ultra Cu) detector

Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.308, T max = 0.631

11571 measured reflections

2546 independent reflections

2485 reflections with I > 3σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.093

S = 1.73

2546 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 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/S1600536810028163/fk2021sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810028163/fk2021Isup2.hkl

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

C16H16BrNO3	Z = 2
Mr = 350.2	F(000) = 356
Triclinic, P1	Dx = 1.554 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54184 Å
a = 7.9103 (3) Å	Cell parameters from 11782 reflections
b = 9.9902 (4) Å	θ = 4.4–66.7°
c = 10.7821 (3) Å	µ = 3.83 mm−1
α = 93.068 (3)°	T = 120 K
β = 108.568 (3)°	Irregular shape, colourless
γ = 109.679 (3)°	0.49 × 0.38 × 0.25 mm
V = 748.10 (5) Å3

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini Ultra Cu) detector	2546 independent reflections
Radiation source: X-ray tube	2485 reflections with I > 3σ(I)
mirror	Rint = 0.023
Detector resolution: 10.3784 pixels mm-1	θmax = 65.1°, θmin = 4.4°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
Tmin = 0.308, Tmax = 0.631	l = −12→12
11571 measured reflections

Refinement on F2	64 constraints
R[F2 > 2σ(F2)] = 0.026	H-atom parameters constrained
wR(F2) = 0.093	Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.0025000002I2]
S = 1.73	(Δ/σ)max = 0.010
2546 reflections	Δρmax = 0.29 e Å−3
190 parameters	Δρmin = −0.28 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	Uiso*/Ueq
Br1	0.74999 (3)	0.08307 (2)	0.325568 (16)	0.02973 (14)
O1	0.27449 (16)	0.17106 (14)	0.96566 (12)	0.0209 (5)
O2	0.28261 (17)	0.27191 (14)	1.21239 (13)	0.0204 (5)
O3	0.58807 (17)	0.49203 (14)	1.37866 (12)	0.0217 (5)
N1	0.7545 (2)	0.28811 (17)	0.86865 (15)	0.0205 (6)
C1	0.5987 (2)	0.27332 (18)	0.88986 (17)	0.0196 (6)
C2	0.6019 (2)	0.33388 (19)	1.01757 (17)	0.0183 (6)
C3	0.4387 (2)	0.27855 (18)	1.05351 (17)	0.0179 (6)
C4	0.4391 (2)	0.33244 (18)	1.17524 (16)	0.0177 (6)
C5	0.6034 (2)	0.44399 (19)	1.26324 (17)	0.0188 (6)
C6	0.7671 (2)	0.50042 (19)	1.22894 (17)	0.0205 (7)
C7	0.7633 (2)	0.4451 (2)	1.10740 (17)	0.0209 (7)
C8	0.2463 (3)	0.0301 (2)	1.0001 (2)	0.0275 (7)
C9	0.1411 (2)	0.3364 (2)	1.16845 (19)	0.0225 (7)
C10	0.7574 (3)	0.5963 (2)	1.4782 (2)	0.0283 (8)
C11	0.7401 (2)	0.23365 (19)	0.74029 (17)	0.0190 (6)
C12	0.8644 (2)	0.16622 (19)	0.73130 (18)	0.0214 (7)
C13	0.8630 (3)	0.1162 (2)	0.60794 (19)	0.0228 (7)
C14	0.7397 (3)	0.1383 (2)	0.49439 (18)	0.0212 (7)
C15	0.6134 (3)	0.2048 (2)	0.50017 (19)	0.0232 (7)
C16	0.6156 (3)	0.2530 (2)	0.62404 (18)	0.0224 (7)
H1	0.477112	0.22121	0.820107	0.0236*
H6	0.880465	0.576586	1.289179	0.0246*
H7	0.875405	0.484421	1.084082	0.0251*
H8a	0.117756	−0.035146	0.948638	0.0329*
H8b	0.336604	−0.004589	0.981472	0.0329*
H8c	0.265545	0.035921	1.093009	0.0329*
H9a	0.039226	0.294309	1.201348	0.0269*
H9b	0.200061	0.438601	1.201714	0.0269*
H9c	0.089588	0.3194	1.073	0.0269*
H10a	0.725742	0.625109	1.551587	0.034*
H10b	0.852651	0.554334	1.508865	0.034*
H10c	0.807226	0.679308	1.440879	0.034*
H12	0.95208	0.154077	0.810937	0.0256*
H13	0.946288	0.067032	0.60173	0.0274*
H15	0.526458	0.217114	0.42029	0.0278*
H16	0.530309	0.300348	0.629778	0.0268*

	U11	U22	U33	U12	U13	U23
Br1	0.03787 (19)	0.03187 (19)	0.02105 (19)	0.00904 (13)	0.01747 (12)	0.00097 (11)
O1	0.0192 (6)	0.0209 (7)	0.0176 (6)	0.0033 (5)	0.0045 (5)	0.0034 (5)
O2	0.0202 (6)	0.0239 (7)	0.0230 (7)	0.0091 (5)	0.0132 (5)	0.0103 (5)
O3	0.0227 (6)	0.0259 (7)	0.0175 (6)	0.0079 (5)	0.0099 (5)	0.0019 (5)
N1	0.0230 (7)	0.0245 (8)	0.0159 (7)	0.0089 (6)	0.0090 (6)	0.0047 (6)
C1	0.0214 (8)	0.0192 (8)	0.0189 (9)	0.0072 (7)	0.0078 (7)	0.0067 (7)
C2	0.0206 (8)	0.0211 (8)	0.0174 (8)	0.0098 (7)	0.0094 (7)	0.0071 (7)
C3	0.0179 (8)	0.0183 (8)	0.0178 (8)	0.0071 (7)	0.0059 (6)	0.0058 (7)
C4	0.0196 (8)	0.0197 (8)	0.0192 (8)	0.0096 (7)	0.0107 (7)	0.0095 (7)
C5	0.0214 (8)	0.0216 (9)	0.0177 (8)	0.0104 (7)	0.0093 (7)	0.0069 (7)
C6	0.0196 (8)	0.0213 (9)	0.0199 (9)	0.0059 (7)	0.0082 (7)	0.0030 (7)
C7	0.0201 (8)	0.0238 (9)	0.0213 (9)	0.0073 (7)	0.0114 (7)	0.0060 (7)
C8	0.0309 (9)	0.0197 (9)	0.0304 (11)	0.0044 (8)	0.0147 (8)	0.0038 (8)
C9	0.0187 (9)	0.0268 (9)	0.0248 (10)	0.0093 (8)	0.0105 (7)	0.0066 (7)
C10	0.0256 (9)	0.0369 (11)	0.0186 (9)	0.0094 (8)	0.0066 (7)	−0.0024 (8)
C11	0.0192 (8)	0.0185 (8)	0.0188 (9)	0.0039 (7)	0.0091 (7)	0.0044 (7)
C12	0.0208 (8)	0.0256 (9)	0.0208 (9)	0.0097 (7)	0.0098 (7)	0.0078 (7)
C13	0.0232 (9)	0.0227 (9)	0.0265 (10)	0.0097 (7)	0.0126 (7)	0.0055 (7)
C14	0.0261 (9)	0.0205 (9)	0.0186 (9)	0.0053 (7)	0.0140 (7)	0.0022 (7)
C15	0.0277 (9)	0.0249 (9)	0.0185 (9)	0.0105 (8)	0.0088 (7)	0.0083 (7)
C16	0.0255 (9)	0.0241 (9)	0.0223 (9)	0.0118 (7)	0.0116 (7)	0.0066 (7)

Br1—C14	1.908 (2)	C8—H8a	0.96
O1—C3	1.3805 (16)	C8—H8b	0.96
O1—C8	1.438 (2)	C8—H8c	0.96
O2—C4	1.377 (2)	C9—H9a	0.96
O2—C9	1.440 (3)	C9—H9b	0.96
O3—C5	1.365 (2)	C9—H9c	0.96
O3—C10	1.4342 (19)	C10—H10a	0.96
N1—C1	1.286 (3)	C10—H10b	0.96
N1—C11	1.415 (3)	C10—H10c	0.96
C1—C2	1.463 (3)	C11—C12	1.390 (3)
C1—H1	0.96	C11—C16	1.395 (3)
C2—C3	1.408 (3)	C12—C13	1.391 (3)
C2—C7	1.3946 (19)	C12—H12	0.96
C3—C4	1.391 (3)	C13—C14	1.383 (3)
C4—C5	1.3990 (19)	C13—H13	0.96
C5—C6	1.403 (3)	C14—C15	1.387 (3)
C6—C7	1.382 (3)	C15—C16	1.388 (3)
C6—H6	0.96	C15—H15	0.96
C7—H7	0.96	C16—H16	0.96
C3—O1—C8	113.46 (13)	O2—C9—H9a	109.4709
C4—O2—C9	112.97 (15)	O2—C9—H9b	109.4713
C5—O3—C10	117.80 (15)	O2—C9—H9c	109.4711
C1—N1—C11	118.43 (13)	H9a—C9—H9b	109.4714
N1—C1—C2	121.70 (13)	H9a—C9—H9c	109.4709
N1—C1—H1	119.1502	H9b—C9—H9c	109.4718
C2—C1—H1	119.1489	O3—C10—H10a	109.4713
C1—C2—C3	119.84 (13)	O3—C10—H10b	109.4716
C1—C2—C7	122.20 (18)	O3—C10—H10c	109.4711
C3—C2—C7	117.96 (17)	H10a—C10—H10b	109.4714
O1—C3—C2	119.60 (16)	H10a—C10—H10c	109.4707
O1—C3—C4	119.38 (16)	H10b—C10—H10c	109.4713
C2—C3—C4	121.01 (13)	N1—C11—C12	117.91 (16)
O2—C4—C3	120.43 (12)	N1—C11—C16	122.8 (2)
O2—C4—C5	119.83 (17)	C12—C11—C16	119.21 (19)
C3—C4—C5	119.66 (17)	C11—C12—C13	120.60 (17)
O3—C5—C4	115.31 (17)	C11—C12—H12	119.6985
O3—C5—C6	124.62 (13)	C13—C12—H12	119.6991
C4—C5—C6	120.06 (17)	C12—C13—C14	118.9 (2)
C5—C6—C7	119.23 (13)	C12—C13—H13	120.5337
C5—C6—H6	120.3876	C14—C13—H13	120.5339
C7—C6—H6	120.3865	Br1—C14—C13	119.31 (18)
C2—C7—C6	122.09 (18)	Br1—C14—C15	118.89 (14)
C2—C7—H7	118.9551	C13—C14—C15	121.8 (2)
C6—C7—H7	118.9554	C14—C15—C16	118.52 (18)
O1—C8—H8a	109.4712	C14—C15—H15	120.7399
O1—C8—H8b	109.4712	C16—C15—H15	120.7397
O1—C8—H8c	109.4713	C11—C16—C15	120.9 (2)
H8a—C8—H8b	109.4713	C11—C16—H16	119.5302
H8a—C8—H8c	109.4709	C15—C16—H16	119.5303
H8b—C8—H8c	109.4714
C8—O1—C3—C2	103.6 (2)	C11—N1—C1—C2	−176.48 (16)
C8—O1—C3—C4	−77.6 (2)	C1—N1—C11—C12	−140.37 (18)
C9—O2—C4—C3	−88.7 (2)	C1—N1—C11—C16	43.7 (3)
C9—O2—C4—C5	94.54 (19)	N1—C1—C2—C3	−159.30 (17)
C10—O3—C5—C4	174.08 (16)	N1—C1—C2—C7	20.0 (3)
C10—O3—C5—C6	−7.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
?—?···?	?	?	?	?