(E)-4-Bromo-N-(2,3,4-trimeth­oxy­benzyl­idene)aniline

Karla Fejfarová; Aliakbar Dehno Khalaji; Michal Dušek

doi:10.1107/S1600536810028163

. 2010 Jul 21;66(Pt 8):o2062. doi: 10.1107/S1600536810028163

(E)-4-Bromo-N-(2,3,4-trimethoxybenzylidene)aniline

Karla Fejfarová ^a,^*, Aliakbar Dehno Khalaji ^b, Michal Dušek ^a

PMCID: PMC3007382 PMID: 21588366

Abstract

The title Schiff base compound, C₁₆H₁₆BrNO₃, 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 _r = 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
Δρ_max = 0.29 e Å⁻³
Δρ_min = −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.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028163/fk2021sup1.cif

e-66-o2062-sup1.cif^{(17.7KB, cif)}

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

e-66-o2062-Isup2.hkl^{(122.7KB, hkl)}

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

Acknowledgments

We acknowledge the Golestan University (GU), the Institutional research plan No. AVOZ1010051 of the Institute of Physics and the Praemium academiae project of the Academy of Sciences of the Czech Republic.

supplementary crystallographic information

Comment

The chemistry of Schiff-bases is very diverse because of a variety of possible substituents with different electron donating and withdrawing groups (Yildiz et al., 2008; Hijji et al., 2009; Karakas et al., 2008). These compounds have been studied for their use as anion sensors (Hijji et al., 2009), antimicrobial activity (Yildiz et al., 2008), photochromism and thermochromism (Hadjoudis et al., 2004) and nonlinear optical properties (Karakas et al., 2008). As a continuation of our work on the synthesis and structural characterization of Schiff-base compounds we report the synthesis and crystal structure of (E)-4-bromo-N-(2,3-dimethoxybenzylidene)aniline (1).

An ORTEP plot, with the atomic numbering scheme is depicted in Fig. 1. Bond lengths in the title compound are normal (Allen et al., 1987). The C1—N1 and C11—N1 bond lengths of 1.286 (3) and 1.415 (3) Å, respectively, conform to the value for a double and single bonds as found in similar Schiff-base compounds (Khalaji et al., 2007; Khalaji & Harrison, 2008; Khalaji et al., 2008; Khalaji & Simpson, 2009; Khalaji et al., 2009; Khalaji et al., 2010). The dihedral angle between the two aromatic rings is 64.02 (6)°, while the plane through the central C1—N1—C1—C2 system is inclined at 21.65 (18)° to the dimethoxyphenyl ring and 42.37 (18)° to the bromobenzene ring. The two methoxy groups attached at C3 and C4 are twisted away from the C2—C7 benzene ring, with corresponding torsion angles C8—O1—C3—C2, C9—O2—C4—C3 of 103.6 (2)°, -88.7 (2)°, respectively. The third methoxy group attached at C5 is almost coplanar with the C2—C7 ring, as shown by the torsion angle C10—O3—C5—C6 of -7.2 (3)°.

Experimental

The title compound was prepared in 83% yield from 2,3,4-trimethoxybenzaldehyde and 4-bromoaniline as reported elsewhere (Khalaji & Harrison, 2008) and recrystallized from chloroform. Anal. Calc. for C₁₆H₁₆BrNO₃: C, 54.87; H, 4.60; N, 4.00%. Found: C, 54.66; H, 4.52; N, 4.06%. IR (KBr pellet, cm-1): 2911–2998 (m, C—H aromatic and aliphatic), 2837 (s, –CH=N–); 1615 (s, C=N), 1413–1594 (C=C aromatic).

Figures

Fig. 1. — The molecular structure of the title compound with atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C₁₆H₁₆BrNO₃	Z = 2
M_r = 350.2	F(000) = 356
Triclinic, P1	D_x = 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

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Data collection

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	R_int = 0.023
Detector resolution: 10.3784 pixels mm^-1	θ_max = 65.1°, θ_min = 4.4°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: analytical (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→11
T_min = 0.308, T_max = 0.631	l = −12→12
11571 measured reflections

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Refinement

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	Δρ_max = 0.29 e Å⁻³
190 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints

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Special details

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.

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

	x	y	z	U_iso*/U_eq
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*

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Atomic displacement parameters (Å²)

	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)

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Geometric parameters (Å, °)

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)

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Hydrogen-bond geometry (Å, °)

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

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Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FK2021).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Brandenburg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Bonn, Germany.
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst.36, 1103.
Hadjoudis, E., Rontoyianni, A., Ambroziak, K., Aziembowska, T. & Mavridis, I. M. (2004). J. Photochem. Photobiol. A, 162, 521–530.
Hijji, Y. M., Barare, B., Kennedy, A. P. & Butcher, R. (2009). Sens. Actuators B, 136, 297–302.
Karakas, A., Univer, H. & Elmali, A. (2008). J. Mol. Struct.877, 152–157.
Khalaji, A. D., Fejfarová, K. & Dušek, M. (2010). Acta Chim. Slov.57, 257–261. [PubMed]
Khalaji, A. D. & Harrison, W. T. A. (2008). Anal. Sci.24, x3–x4.
Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553. [DOI] [PMC free article] [PubMed]
Khalaji, A. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, o4257.
Khalaji, A. D., Weil, M., Gotoh, K. & Ishida, H. (2009). Acta Cryst. E65, o436. [DOI] [PMC free article] [PubMed]
Khalaji, A. D., Welter, R., Amirnasr, M. & Barry, A. H. (2008). Anal. Sci.24, x138–x139.
Oxford Diffraction (2009). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.
Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006 Institute of Physics, Prague, Czech Republic.
Yildiz, M., Unver, H., Dulger, B., Erdener, D., Ocak, N., Erdonmez, A. & Durlu, T. N. (2008). J. Mol. Struct.738, 253–260.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810028163/fk2021sup1.cif

e-66-o2062-sup1.cif^{(17.7KB, cif)}

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

e-66-o2062-Isup2.hkl^{(122.7KB, hkl)}

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

[bb1] Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.

[bb2] Brandenburg, K. & Putz, H. (2005). DIAMOND Crystal Impact GbR, Bonn, Germany.

[bb3] Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst.36, 1103.

[bb4] Hadjoudis, E., Rontoyianni, A., Ambroziak, K., Aziembowska, T. & Mavridis, I. M. (2004). J. Photochem. Photobiol. A, 162, 521–530.

[bb5] Hijji, Y. M., Barare, B., Kennedy, A. P. & Butcher, R. (2009). Sens. Actuators B, 136, 297–302.

[bb6] Karakas, A., Univer, H. & Elmali, A. (2008). J. Mol. Struct.877, 152–157.

[bb7] Khalaji, A. D., Fejfarová, K. & Dušek, M. (2010). Acta Chim. Slov.57, 257–261. [PubMed]

[bb8] Khalaji, A. D. & Harrison, W. T. A. (2008). Anal. Sci.24, x3–x4.

[bb9] Khalaji, A. D. & Simpson, J. (2009). Acta Cryst. E65, o553. [DOI] [PMC free article] [PubMed]

[bb10] Khalaji, A. D., Slawin, A. M. Z. & Woollins, J. D. (2007). Acta Cryst. E63, o4257.

[bb11] Khalaji, A. D., Weil, M., Gotoh, K. & Ishida, H. (2009). Acta Cryst. E65, o436. [DOI] [PMC free article] [PubMed]

[bb12] Khalaji, A. D., Welter, R., Amirnasr, M. & Barry, A. H. (2008). Anal. Sci.24, x138–x139.

[bb13] Oxford Diffraction (2009). CrysAlis PRO Oxford Diffraction Ltd, Yarnton, England.

[bb14] Petříček, V., Dušek, M. & Palatinus, L. (2006). JANA2006 Institute of Physics, Prague, Czech Republic.

[bb15] Yildiz, M., Unver, H., Dulger, B., Erdener, D., Ocak, N., Erdonmez, A. & Durlu, T. N. (2008). J. Mol. Struct.738, 253–260.

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(E)-4-Bromo-N-(2,3,4-trimethoxybenzylidene)aniline

Karla Fejfarová

Aliakbar Dehno Khalaji

Michal Dušek

Abstract

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Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

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Fig. 1.

Crystal data

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Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

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(E)-4-Bromo-N-(2,3,4-trimeth­oxy­benzyl­idene)aniline

Karla Fejfarová

Aliakbar Dehno Khalaji

Michal Dušek

Abstract

Related literature

Experimental

Crystal data

Data collection

Refinement

Supplementary Material

Acknowledgments

supplementary crystallographic information

Comment

Experimental

Refinement

Figures

Fig. 1.

Crystal data

Data collection

Refinement

Special details

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

Atomic displacement parameters (Å2)

Geometric parameters (Å, °)

Hydrogen-bond geometry (Å, °)

Footnotes

References

Associated Data

Supplementary Materials

ACTIONS

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RESOURCES

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(E)-4-Bromo-N-(2,3,4-trimethoxybenzylidene)aniline

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²)

Atomic displacement parameters (Å²)