3,4-Bis(4-bromo­phen­yl)-N-phenyl­maleimide

Liu, Y.; Zheng, S.; Zhou, J.; Gao, D.; Du, Z.-T.

doi:10.1107/S1600536811014152

organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Page o1198

doi:10.1107/S1600536811014152

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3,4-Bis(4-bromophenyl)-N-phenylmaleimide

Yong Liu,^a Shuai Zheng,^b Jing Zhou,^b Dongmei Gao ^b and Zhen-Ting Du ^b ^*

^aMedical College, Northwest University for Nationalities, Lanzhou 730030, Gansu Province, People's Republic of China, and ^bCollege of Science, Northwest A&F University, Yangling 712100, Shannxi Province, People's Republic of China
^*Correspondence e-mail: duzt@nwsuaf.edu.cn

(Received 2 April 2011; accepted 15 April 2011; online 22 April 2011)

In the title molecule, C₂₂H₁₃Br₂NO₂, the three benzene rings are arranged in a propeller-like fashion around the central malemide ring, making dihedral angles of 48.2 (4), 30.2 (4) and 34.8 (4)° with the malemide ring. The C—C single-bond lengths connecting benzene groups and maleimide are significantly shorter [C—C = 1.468 (9) and 1.478 (9) Å] than a typical Csp³—Csp³ single bond, indicating partial conjugation between the benzene and the maleimide. A weak nonclassical C—H⋯O hydrogen bond helps to stabilize the crystal structure.

Related literature

For general background to 3,4-diaryl-substituted maleimide derivatives, see: Fujii et al. (2001 ); Onimura et al. (2010 ); Shorunov et al. (2006 ).

Experimental

Crystal data

C₂₂H₁₃Br₂NO₂
M_r = 483.13
Monoclinic, P 2₁ /c
a = 10.844 (5) Å
b = 18.594 (9) Å
c = 9.602 (5) Å
β = 102.760 (6)°
V = 1888.3 (16) Å³
Z = 4
Mo Kα radiation
μ = 4.31 mm⁻¹
T = 296 K
0.32 × 0.30 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1998 ) T_min = 0.339, T_max = 0.424
8594 measured reflections
3382 independent reflections
1427 reflections with I > 2σ(I)
R_int = 0.117

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.133
S = 0.94
3382 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.71 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O1ⁱ	0.93	2.41	3.267 (9)	153
Symmetry code: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2001 ); 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811014152/rk2272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811014152/rk2272Isup2.hkl

checkCIF report

Comment top

3,4-Diaryl-substituted maleimide is a conjugated unit which has interesting optical and electronic properties. A number of 3,4-diaryl-substituted maleimide derivatives have been designed and synthesized to be used as monomer of some electro–optic polymers (Shorunov et al., 2006; Onimura et al., 2010). In the course of exploring new electro–optic compounds, we obtained a intermediate compound 3,4-bis(4-bromophenyl)-N-phenylmaleimide I. Here we report the structure and synthesis of title compound.

The molecule holds four rings. The maleimide ring locates the core position, and the other three benzene rings are arranged in a propeller–like fashion around the central malemide 5–membering ring with the dihedral angeles being 48.2 (4)° (C1–C6), 30.2 (4)° (C9–C14) and 34.8 (4)° (C17–C22). The C—C single bond lengths conecting benzene groups and maleimide unit are respectively 1.468 (9)Å (C4—C7) and 1.478 (9)Å (C17—C18), which are obviously shorter than typical Csp³—Csp³ single bond. This means that the bonding between the benzenes and the maleimide is quite conjugated.

The molecules of I are crystalized in P2₁/c space group which is different from that of N–3,4–triphenylmaleimide (Pbca, Fujii et al., 2001). There are no classic hydrogen bonds in this crystal structure. However, the weak intermolecular interaction C21—H21···O1ⁱ is helpful to the stabilization of the packing (Fig. 2). This intermolecular non–classical H–bond is characterized by the parameters: bond lengths of 0.93Å (C21—H21), 2.41Å (H21···O1ⁱ), 3.267 (9)Å (C21···O1ⁱ) and angle 153° (C21—H21···O1ⁱ). Symmetry code: (i) 1-x, -1/2+y, 1/2-z.

Related literature top

For general background to 3,4-diaryl-substituted maleimide derivatives, see: Fujii et al. (2001); Onimura et al. (2010); Shorunov et al. (2006).

Experimental top

3,4–Bis(4–bromophenyl)maleic anhydride (0.60 g, 1.47 mmol), 4–methylbenzenesulfonic acid (0.30 g, 3.26 mmol) and H₂SO₄ (2 ml) were dissolved in N,N–dimethylformamide (DMF, 1.0 ml) and toluene (20 ml) mixed solvent. After heating the mixture to refluxing, a toluene solution of anilin (0.20 g, 2.17 mmol) was slowly added. After stirring for 2 h, the mixture was cooled to 333 K and poured into 8% Na₂CO₃ solution and further stirred for 10 min. The solution was extracted with toluene and dried over Na₂SO₄. After removing the solvent, the crude product was purified by recrystallization from ethanol, affording the title compound, I, (0.51 g, 72%). Then the compound I was dissolved in THF, and yellow crystals were formed on slow evaporation at room temperature over one week.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of I with the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The molecular packing of I along b axis.

3,4-bis(4-bromophenyl)-1-phenyl-2,5-dihydro-1H-pyrrole-2,5-dione top

Crystal data top

C₂₂H₁₃Br₂NO₂	F(000) = 952
M_r = 483.13	D_x = 1.699 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1226 reflections
a = 10.844 (5) Å	θ = 2.2–20.8°
b = 18.594 (9) Å	µ = 4.31 mm⁻¹
c = 9.602 (5) Å	T = 296 K
β = 102.760 (6)°	Block, yellow
V = 1888.3 (16) Å³	0.32 × 0.30 × 0.24 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3382 independent reflections
Radiation source: fine–focus sealed tube	1427 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.117
ϕ and ω scans	θ_max = 25.2°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	h = −12→12
T_min = 0.339, T_max = 0.424	k = −22→21
8594 measured reflections	l = −9→11

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H-atom parameters constrained
S = 0.94	w = 1/[σ²(F_o²) + (0.0468P)²] where P = (F_o² + 2F_c²)/3
3382 reflections	(Δ/σ)_max = 0.001
244 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

Crystal data top

C₂₂H₁₃Br₂NO₂	V = 1888.3 (16) Å³
M_r = 483.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.844 (5) Å	µ = 4.31 mm⁻¹
b = 18.594 (9) Å	T = 296 K
c = 9.602 (5) Å	0.32 × 0.30 × 0.24 mm
β = 102.760 (6)°

Data collection top

Bruker APEXII CCD diffractometer	3382 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1998)	1427 reflections with I > 2σ(I)
T_min = 0.339, T_max = 0.424	R_int = 0.117
8594 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 0.94	Δρ_max = 0.51 e Å⁻³
3382 reflections	Δρ_min = −0.71 e Å⁻³
244 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 fornegative 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.

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

	x	y	z	U_iso*/U_eq
Br1	0.18239 (9)	1.08051 (4)	−0.16015 (9)	0.0659 (4)
Br2	0.12170 (9)	0.59744 (5)	−0.09998 (9)	0.0681 (4)
C1	0.2818 (7)	1.0177 (4)	−0.0272 (8)	0.042 (2)
C2	0.3009 (7)	1.0324 (4)	0.1166 (8)	0.044 (2)
H2	0.2661	1.0735	0.1474	0.052*
C3	0.3718 (7)	0.9859 (4)	0.2152 (7)	0.046 (2)
H3	0.3854	0.9965	0.3121	0.055*
C4	0.4223 (7)	0.9244 (3)	0.1720 (7)	0.037 (2)
C5	0.4019 (7)	0.9103 (4)	0.0241 (7)	0.041 (2)
H5	0.4353	0.8689	−0.0080	0.050*
C6	0.3333 (8)	0.9573 (4)	−0.0718 (7)	0.049 (2)
H6	0.3214	0.9480	−0.1690	0.058*
C7	0.4950 (7)	0.8740 (4)	0.2765 (7)	0.0317 (19)
C8	0.5979 (7)	0.8995 (4)	0.3949 (7)	0.037 (2)
C9	0.7668 (7)	0.8405 (4)	0.5799 (7)	0.0324 (19)
C10	0.8549 (8)	0.8948 (4)	0.5883 (8)	0.049 (2)
H10	0.8449	0.9299	0.5176	0.059*
C11	0.9570 (8)	0.8967 (5)	0.7012 (9)	0.064 (3)
H11	1.0169	0.9329	0.7067	0.077*
C12	0.9715 (9)	0.8455 (5)	0.8061 (8)	0.066 (3)
H12	1.0385	0.8483	0.8852	0.079*
C13	0.8877 (9)	0.7907 (5)	0.7936 (9)	0.067 (3)
H13	0.9013	0.7541	0.8612	0.080*
C14	0.7840 (8)	0.7881 (4)	0.6845 (8)	0.049 (2)
H14	0.7252	0.7513	0.6802	0.059*
C15	0.5930 (7)	0.7768 (4)	0.4054 (7)	0.038 (2)
C16	0.4904 (7)	0.8021 (4)	0.2827 (7)	0.0321 (19)
C17	0.3999 (8)	0.7505 (4)	0.1988 (7)	0.035 (2)
C18	0.2750 (8)	0.7690 (4)	0.1499 (8)	0.050 (2)
H18	0.2470	0.8136	0.1741	0.060*
C19	0.1900 (8)	0.7226 (4)	0.0653 (7)	0.052 (2)
H19	0.1053	0.7352	0.0353	0.063*
C20	0.2331 (8)	0.6571 (4)	0.0260 (7)	0.043 (2)
C21	0.3549 (8)	0.6361 (4)	0.0806 (7)	0.046 (2)
H21	0.3816	0.5905	0.0607	0.055*
C22	0.4388 (7)	0.6829 (4)	0.1659 (7)	0.036 (2)
H22	0.5221	0.6687	0.2014	0.044*
N1	0.6588 (6)	0.8394 (3)	0.4625 (6)	0.0341 (16)
O1	0.6229 (5)	0.9610 (3)	0.4283 (5)	0.0494 (15)
O2	0.6167 (5)	0.7165 (3)	0.4467 (5)	0.0480 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0834 (8)	0.0516 (6)	0.0525 (6)	0.0141 (5)	−0.0068 (5)	0.0128 (4)
Br2	0.0699 (7)	0.0590 (6)	0.0689 (7)	−0.0182 (5)	0.0015 (5)	−0.0198 (5)
C1	0.056 (6)	0.032 (5)	0.034 (5)	0.004 (4)	0.002 (4)	0.000 (4)
C2	0.058 (6)	0.034 (5)	0.043 (5)	0.007 (4)	0.021 (5)	−0.006 (4)
C3	0.073 (7)	0.030 (5)	0.031 (5)	0.008 (5)	0.005 (4)	−0.006 (4)
C4	0.055 (6)	0.018 (4)	0.037 (5)	−0.003 (4)	0.011 (4)	−0.002 (4)
C5	0.064 (6)	0.027 (5)	0.033 (4)	0.012 (4)	0.011 (4)	−0.008 (4)
C6	0.078 (7)	0.048 (5)	0.019 (4)	0.003 (5)	0.008 (4)	−0.007 (4)
C7	0.043 (6)	0.025 (4)	0.027 (4)	0.002 (4)	0.009 (4)	−0.006 (3)
C8	0.047 (6)	0.031 (5)	0.034 (5)	0.000 (4)	0.009 (4)	0.002 (4)
C9	0.039 (6)	0.030 (4)	0.029 (5)	0.000 (4)	0.010 (4)	−0.011 (4)
C10	0.050 (6)	0.054 (6)	0.041 (5)	0.002 (5)	0.004 (5)	0.014 (4)
C11	0.060 (7)	0.055 (6)	0.072 (6)	−0.007 (5)	0.003 (5)	0.008 (5)
C12	0.060 (7)	0.080 (7)	0.047 (6)	0.011 (6)	−0.012 (5)	0.003 (5)
C13	0.072 (8)	0.064 (7)	0.054 (6)	−0.008 (6)	−0.010 (6)	0.021 (5)
C14	0.056 (7)	0.035 (5)	0.052 (6)	0.003 (4)	0.004 (5)	0.019 (4)
C15	0.055 (6)	0.035 (5)	0.025 (5)	−0.003 (4)	0.014 (4)	0.002 (4)
C16	0.051 (6)	0.023 (4)	0.022 (4)	0.004 (4)	0.007 (4)	−0.001 (3)
C17	0.058 (7)	0.024 (5)	0.023 (4)	−0.001 (4)	0.011 (4)	0.003 (3)
C18	0.054 (7)	0.034 (5)	0.059 (6)	0.008 (5)	0.007 (5)	−0.006 (4)
C19	0.058 (7)	0.038 (5)	0.053 (5)	0.003 (5)	−0.004 (5)	−0.010 (4)
C20	0.049 (7)	0.038 (5)	0.038 (5)	−0.005 (4)	0.000 (4)	−0.003 (4)
C21	0.075 (8)	0.029 (5)	0.041 (5)	−0.006 (5)	0.027 (5)	−0.004 (4)
C22	0.047 (6)	0.027 (5)	0.037 (5)	−0.005 (4)	0.012 (4)	−0.003 (4)
N1	0.039 (4)	0.030 (4)	0.031 (4)	−0.008 (3)	0.004 (3)	−0.001 (3)
O1	0.067 (4)	0.028 (3)	0.046 (3)	−0.003 (3)	−0.005 (3)	−0.005 (3)
O2	0.066 (4)	0.028 (3)	0.043 (3)	0.000 (3)	−0.004 (3)	0.004 (2)

Geometric parameters (Å, º) top

Br1—C1	1.883 (7)	C11—C12	1.369 (10)
Br2—C20	1.873 (7)	C11—H11	0.9300
C1—C6	1.365 (9)	C12—C13	1.352 (11)
C1—C2	1.378 (8)	C12—H12	0.9300
C2—C3	1.384 (9)	C13—C14	1.357 (9)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.371 (9)	C14—H14	0.9300
C3—H3	0.9300	C15—O2	1.198 (7)
C4—C5	1.414 (8)	C15—N1	1.412 (8)
C4—C7	1.468 (9)	C15—C16	1.506 (9)
C5—C6	1.365 (9)	C16—C17	1.478 (9)
C5—H5	0.9300	C17—C18	1.375 (10)
C6—H6	0.9300	C17—C22	1.385 (9)
C7—C16	1.339 (9)	C18—C19	1.387 (9)
C7—C8	1.484 (9)	C18—H18	0.9300
C8—O1	1.202 (7)	C19—C20	1.386 (9)
C8—N1	1.385 (8)	C19—H19	0.9300
C9—C10	1.380 (9)	C20—C21	1.366 (10)
C9—C14	1.383 (8)	C21—C22	1.388 (9)
C9—N1	1.435 (8)	C21—H21	0.9300
C10—C11	1.369 (10)	C22—H22	0.9300
C10—H10	0.9300

C6—C1—C2	119.7 (6)	C11—C12—H12	120.3
C6—C1—Br1	120.7 (6)	C12—C13—C14	121.4 (8)
C2—C1—Br1	119.6 (6)	C12—C13—H13	119.3
C1—C2—C3	120.0 (7)	C14—C13—H13	119.3
C1—C2—H2	120.0	C13—C14—C9	119.4 (8)
C3—C2—H2	120.0	C13—C14—H14	120.3
C4—C3—C2	120.9 (7)	C9—C14—H14	120.3
C4—C3—H3	119.6	O2—C15—N1	126.1 (7)
C2—C3—H3	119.6	O2—C15—C16	128.3 (7)
C3—C4—C5	118.3 (6)	N1—C15—C16	105.6 (6)
C3—C4—C7	121.0 (6)	C7—C16—C17	130.6 (7)
C5—C4—C7	120.6 (6)	C7—C16—C15	108.6 (6)
C6—C5—C4	120.0 (7)	C17—C16—C15	120.7 (6)
C6—C5—H5	120.0	C18—C17—C22	118.5 (7)
C4—C5—H5	120.0	C18—C17—C16	120.6 (7)
C5—C6—C1	121.1 (7)	C22—C17—C16	121.0 (7)
C5—C6—H6	119.5	C17—C18—C19	121.4 (7)
C1—C6—H6	119.5	C17—C18—H18	119.3
C16—C7—C4	130.3 (6)	C19—C18—H18	119.3
C16—C7—C8	108.3 (6)	C18—C19—C20	119.0 (8)
C4—C7—C8	121.3 (6)	C18—C19—H19	120.5
O1—C8—N1	125.9 (7)	C20—C19—H19	120.5
O1—C8—C7	126.6 (7)	C21—C20—C19	120.1 (7)
N1—C8—C7	107.5 (6)	C21—C20—Br2	120.7 (6)
C10—C9—C14	119.5 (7)	C19—C20—Br2	119.2 (6)
C10—C9—N1	119.4 (6)	C20—C21—C22	120.0 (7)
C14—C9—N1	121.1 (7)	C20—C21—H21	120.0
C11—C10—C9	119.6 (7)	C22—C21—H21	120.0
C11—C10—H10	120.2	C17—C22—C21	120.6 (7)
C9—C10—H10	120.2	C17—C22—H22	119.7
C10—C11—C12	120.4 (9)	C21—C22—H22	119.7
C10—C11—H11	119.8	C8—N1—C15	109.6 (6)
C12—C11—H11	119.8	C8—N1—C9	125.3 (6)
C13—C12—C11	119.5 (8)	C15—N1—C9	124.9 (6)
C13—C12—H12	120.3

C6—C1—C2—C3	−0.1 (12)	O2—C15—C16—C7	178.1 (8)
Br1—C1—C2—C3	178.8 (6)	N1—C15—C16—C7	−2.8 (8)
C1—C2—C3—C4	−1.0 (12)	O2—C15—C16—C17	2.3 (12)
C2—C3—C4—C5	1.0 (11)	N1—C15—C16—C17	−178.6 (6)
C2—C3—C4—C7	−178.5 (7)	C7—C16—C17—C18	−32.3 (12)
C3—C4—C5—C6	−0.1 (11)	C15—C16—C17—C18	142.5 (7)
C7—C4—C5—C6	179.5 (7)	C7—C16—C17—C22	146.8 (8)
C4—C5—C6—C1	−1.0 (12)	C15—C16—C17—C22	−38.4 (10)
C2—C1—C6—C5	1.1 (12)	C22—C17—C18—C19	−2.3 (11)
Br1—C1—C6—C5	−177.8 (6)	C16—C17—C18—C19	176.9 (7)
C3—C4—C7—C16	135.2 (9)	C17—C18—C19—C20	−1.9 (12)
C5—C4—C7—C16	−44.3 (12)	C18—C19—C20—C21	5.8 (12)
C3—C4—C7—C8	−48.7 (10)	C18—C19—C20—Br2	−175.2 (6)
C5—C4—C7—C8	131.7 (7)	C19—C20—C21—C22	−5.5 (12)
C16—C7—C8—O1	−174.1 (8)	Br2—C20—C21—C22	175.5 (5)
C4—C7—C8—O1	9.1 (12)	C18—C17—C22—C21	2.7 (10)
C16—C7—C8—N1	4.7 (8)	C16—C17—C22—C21	−176.5 (6)
C4—C7—C8—N1	−172.1 (6)	C20—C21—C22—C17	1.2 (11)
C14—C9—C10—C11	−1.1 (11)	O1—C8—N1—C15	172.3 (7)
N1—C9—C10—C11	179.0 (7)	C7—C8—N1—C15	−6.5 (8)
C9—C10—C11—C12	−0.5 (13)	O1—C8—N1—C9	−3.4 (12)
C10—C11—C12—C13	3.5 (14)	C7—C8—N1—C9	177.8 (6)
C11—C12—C13—C14	−4.8 (15)	O2—C15—N1—C8	−175.1 (7)
C12—C13—C14—C9	3.2 (14)	C16—C15—N1—C8	5.8 (8)
C10—C9—C14—C13	−0.2 (11)	O2—C15—N1—C9	0.6 (12)
N1—C9—C14—C13	179.7 (7)	C16—C15—N1—C9	−178.5 (6)
C4—C7—C16—C17	−9.3 (14)	C10—C9—N1—C8	−33.2 (10)
C8—C7—C16—C17	174.2 (7)	C14—C9—N1—C8	146.9 (7)
C4—C7—C16—C15	175.3 (7)	C10—C9—N1—C15	151.7 (7)
C8—C7—C16—C15	−1.1 (8)	C14—C9—N1—C15	−28.2 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.93	2.41	3.267 (9)	153

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₃Br₂NO₂
M_r	483.13
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.844 (5), 18.594 (9), 9.602 (5)
β (°)	102.760 (6)
V (Å³)	1888.3 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	4.31
Crystal size (mm)	0.32 × 0.30 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1998)
T_min, T_max	0.339, 0.424
No. of measured, independent and observed [I > 2σ(I)] reflections	8594, 3382, 1427
R_int	0.117
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.133, 0.94
No. of reflections	3382
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.71

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O1ⁱ	0.93	2.41	3.267 (9)	153

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

Acknowledgements

Financial support from the Fundamental Research Funds for the Central Universities in NWSUAF (QN2009048) and the Excellent Young Funds 211020712 is greatly appreciated.

References

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