2-(2-Bromo­eth­yl)isoindoline-1,3-dione

Sun, X.-Q.; An, D.; Shao, Y.

doi:10.1107/S1600536811039808

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2832

doi:10.1107/S1600536811039808

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2-(2-Bromoethyl)isoindoline-1,3-dione

Xiao-Qiang Sun,^a Dong An ^a and Ying Shao ^a ^*

^aKey Laboratory of Fine Petrochemical Engineering, Changzhou University, Changzhou 213164, Jiangsu, People's Republic of China
^*Correspondence e-mail: yingshao@cczu.edu.cn

(Received 23 September 2011; accepted 28 September 2011; online 5 October 2011)

The asymmetric unit of the title compound, C₁₀H₈BrNO₂, contains three crystallographically independent molecules. Two of the N—C—C—Br side chains adopt anti conformations [torsion angles = −179.8 (5) and −179.4 (4)°] and the other is gauche [−66.5 (6)°]. The crystal structure features short Br⋯O [3.162 (5) Å] contacts, C—H⋯O hydrogen bonds and numerous π–π stacking interactions [centroid–centroid separations = 3.517 (4)–3.950 (4) Å].

Related literature

For general background to and applications of the title compound, see: Sheng et al. (2007 ). For the preparation, see: Clouet & Juhl (1994 ).

Experimental

Crystal data

C₁₀H₈BrNO₂
M_r = 254.08
Triclinic, $[P \overline 1]$
a = 8.575 (2) Å
b = 11.067 (3) Å
c = 16.333 (5) Å
α = 99.001 (6)°
β = 96.164 (5)°
γ = 102.259 (6)°
V = 1480.2 (7) Å³
Z = 6
Mo Kα radiation
μ = 4.14 mm⁻¹
T = 297 K
0.25 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.370, T_max = 0.437
7716 measured reflections
5043 independent reflections
3241 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.177
S = 1.00
5043 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.64 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O6ⁱ	0.93	2.59	3.301 (9)	133
C10—H10A⋯O3ⁱⁱ	0.97	2.48	3.409 (8)	161
C10—H10B⋯O5ⁱⁱⁱ	0.97	2.60	3.533 (9)	163
C13—H13⋯O4^iv	0.93	2.52	3.448 (8)	175
C14—H14⋯O1	0.93	2.59	3.495 (10)	165
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+1, -y+1, -z+1; (iii) x-1, y-1, z; (iv) x+1, y, z.

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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 I, global. DOI: 10.1107/S1600536811039808/hb6417sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039808/hb6417Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039808/hb6417Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536811039808/hb6417Isup4.cml

checkCIF report

Comment top

The title compound, C₁₀H₈BrNO₂, which is an important aminoethylation reagent in the classic Gabriel Synthesis (Sheng et al., 2007), was prepared by nucleophilic substitution of 1,2-dibromoethane with potassium phthalimide in DMF at room temperature (Clouet et al., 1994). The title compound crystallizes in space group P1 with three crystallographically independent molecules in the asymmetric unit, designated A, B and C (Fig. 1). In the crystal, the phthalimide rings are almost coplanar [r.m.s. deviations = 0.0681 (A), 0.0125 (B), 0.0113 (C) Å, respectively]. The molecular geometries of all molecules are essentiall similar, except for the BrCH₂CH₂ groups adopting slightly different zigzag conformations.

An interesting feature of the crystal structure is the short non-hydrogen Br···O interactions (table 1), together with intra- and inter-molecular C—H···O hydrogen bonding interactions (table 2), which links the molecules into an extended three-dimensional network, as shown in Fig. 2. The crystal structure is further stabilized by intermolecular π–π stacking interactions invoving the benzene and maleinimide rings [centroid-centroid distances = 3.517 (4) - 3.950 (4) Å].

Related literature top

For general background to and applications of the title compound, see: Sheng et al. (2007). For the preparation, see: Clouet & Juhl (1994).

Experimental top

The title compound was prepared according to literature procedures (Clouet et al., 1994). Yield: 86%. Colourless blocks were obtained by slow evaporation of EtOH.

Computing details top

Data collection: APEX2 (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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. View of the title compound, showing 50% probability ellipsoids.
	Fig. 2. Perspective view of the packing of the title compound along b direction. Labels of atoms have been omitted for clarity.

2-(2-Bromoethyl)isoindoline-1,3-dione top

Crystal data top

C₁₀H₈BrNO₂	Z = 6
M_r = 254.08	F(000) = 756
Triclinic, P1	D_x = 1.710 Mg m⁻³
Hall symbol: -P 1	Melting point: 356.0(3) K
a = 8.575 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.067 (3) Å	Cell parameters from 3260 reflections
c = 16.333 (5) Å	θ = 2.5–27.1°
α = 99.001 (6)°	µ = 4.14 mm⁻¹
β = 96.164 (5)°	T = 297 K
γ = 102.259 (6)°	Block, colorless
V = 1480.2 (7) Å³	0.25 × 0.23 × 0.20 mm

Data collection top

Bruker APEXII CCD diffractometer	5043 independent reflections
Radiation source: fine-focus sealed tube	3241 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −10→10
T_min = 0.370, T_max = 0.437	k = −7→13
7716 measured reflections	l = −19→19

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.177	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.1033P)²] where P = (F_o² + 2F_c²)/3
5043 reflections	(Δ/σ)_max < 0.001
379 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.64 e Å⁻³

Crystal data top

C₁₀H₈BrNO₂	γ = 102.259 (6)°
M_r = 254.08	V = 1480.2 (7) Å³
Triclinic, P1	Z = 6
a = 8.575 (2) Å	Mo Kα radiation
b = 11.067 (3) Å	µ = 4.14 mm⁻¹
c = 16.333 (5) Å	T = 297 K
α = 99.001 (6)°	0.25 × 0.23 × 0.20 mm
β = 96.164 (5)°

Data collection top

Bruker APEXII CCD diffractometer	5043 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	3241 reflections with I > 2σ(I)
T_min = 0.370, T_max = 0.437	R_int = 0.042
7716 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.177	H-atom parameters constrained
S = 1.00	Δρ_max = 0.83 e Å⁻³
5043 reflections	Δρ_min = −0.64 e Å⁻³
379 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Br2	0.05219 (9)	0.17632 (7)	0.29910 (5)	0.0612 (3)
Br1	0.22870 (8)	0.96923 (6)	0.46532 (5)	0.0495 (2)
Br3	1.05699 (13)	0.37156 (10)	0.10602 (7)	0.0923 (4)
C1	0.4862 (9)	−0.2168 (6)	0.0232 (4)	0.0491 (17)
H1	0.3998	−0.2820	−0.0034	0.059*
C2	0.6406 (9)	−0.2208 (7)	0.0145 (4)	0.0538 (19)
H2	0.6596	−0.2922	−0.0173	0.065*
C3	0.7710 (9)	−0.1236 (8)	0.0510 (5)	0.059 (2)
H3	0.8748	−0.1300	0.0428	0.070*
C4	0.7475 (8)	−0.0169 (7)	0.0997 (5)	0.0528 (18)
H4	0.8346	0.0492	0.1242	0.063*
C5	0.5920 (7)	−0.0105 (6)	0.1114 (4)	0.0393 (15)
C6	0.4630 (8)	−0.1100 (5)	0.0740 (4)	0.0382 (15)
C7	0.3144 (8)	−0.0779 (6)	0.0967 (4)	0.0441 (16)
C8	0.5291 (8)	0.0885 (6)	0.1586 (4)	0.0443 (16)
C9	0.2475 (8)	0.1140 (7)	0.1804 (5)	0.0511 (18)
H9A	0.2939	0.2036	0.1878	0.061*
H9B	0.1499	0.0940	0.1400	0.061*
C10	0.2073 (8)	0.0820 (7)	0.2603 (4)	0.0503 (17)
H10A	0.3041	0.1032	0.3013	0.060*
H10B	0.1612	−0.0075	0.2533	0.060*
C11	0.5109 (7)	0.6382 (5)	0.4534 (4)	0.0365 (14)
C12	0.6682 (8)	0.6298 (6)	0.4518 (5)	0.0507 (18)
H12	0.7518	0.6849	0.4893	0.061*
C13	0.6980 (8)	0.5376 (7)	0.3930 (5)	0.054 (2)
H13	0.8037	0.5308	0.3906	0.065*
C14	0.5758 (9)	0.4553 (7)	0.3379 (5)	0.0532 (19)
H14	0.6008	0.3943	0.2989	0.064*
C15	0.4148 (9)	0.4604 (6)	0.3386 (5)	0.0514 (18)
H15	0.3311	0.4043	0.3016	0.062*
C16	0.3882 (7)	0.5545 (6)	0.3979 (4)	0.0371 (14)
C17	0.2320 (7)	0.5819 (6)	0.4174 (4)	0.0389 (15)
C18	0.4407 (7)	0.7225 (5)	0.5093 (4)	0.0373 (15)
C19	0.1552 (8)	0.7387 (6)	0.5261 (4)	0.0468 (17)
H19A	0.2082	0.7887	0.5799	0.056*
H19B	0.0719	0.6707	0.5364	0.056*
C20	0.0780 (7)	0.8198 (5)	0.4764 (5)	0.0446 (17)
H20A	−0.0089	0.8432	0.5038	0.054*
H20B	0.0317	0.7716	0.4211	0.054*
C21	0.3965 (9)	0.6962 (7)	0.2211 (5)	0.058 (2)
H21	0.3061	0.6374	0.1915	0.069*
C22	0.3827 (9)	0.8007 (7)	0.2763 (5)	0.057 (2)
H22	0.2808	0.8113	0.2852	0.069*
C23	0.5206 (9)	0.8916 (7)	0.3192 (5)	0.0545 (19)
H23	0.5093	0.9624	0.3550	0.065*
C24	0.6708 (9)	0.8747 (7)	0.3077 (4)	0.0510 (17)
H24	0.7627	0.9332	0.3360	0.061*
C25	0.6838 (8)	0.7710 (6)	0.2544 (4)	0.0412 (15)
C26	0.5487 (8)	0.6835 (6)	0.2123 (4)	0.0433 (16)
C27	0.6050 (8)	0.5849 (6)	0.1569 (5)	0.0495 (17)
C28	0.8293 (8)	0.7294 (6)	0.2302 (4)	0.0450 (16)
C29	0.8764 (10)	0.5529 (7)	0.1255 (5)	0.061 (2)
H29A	0.9743	0.6128	0.1211	0.074*
H29B	0.8219	0.5150	0.0693	0.074*
C30	0.9173 (10)	0.4537 (7)	0.1703 (5)	0.064 (2)
H30A	0.8199	0.3931	0.1744	0.077*
H30B	0.9723	0.4911	0.2264	0.077*
N1	0.3639 (6)	0.0434 (5)	0.1479 (3)	0.0419 (13)
N2	0.2731 (6)	0.6854 (4)	0.4833 (3)	0.0363 (12)
N3	0.7699 (7)	0.6185 (5)	0.1727 (4)	0.0514 (15)
O1	0.6004 (6)	0.1893 (5)	0.1976 (4)	0.0694 (16)
O2	0.1764 (6)	−0.1350 (5)	0.0784 (4)	0.0734 (17)
O3	0.5045 (5)	0.8060 (4)	0.5681 (3)	0.0544 (13)
O4	0.0969 (5)	0.5313 (5)	0.3867 (3)	0.0596 (14)
O5	0.9687 (6)	0.7775 (5)	0.2544 (4)	0.0713 (16)
O6	0.5281 (7)	0.4928 (5)	0.1101 (4)	0.0819 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br2	0.0557 (5)	0.0705 (5)	0.0602 (5)	0.0213 (4)	0.0216 (4)	0.0028 (4)
Br1	0.0543 (4)	0.0379 (4)	0.0570 (5)	0.0104 (3)	0.0134 (3)	0.0080 (3)
Br3	0.1184 (8)	0.0883 (7)	0.0948 (7)	0.0682 (6)	0.0399 (6)	0.0136 (6)
C1	0.051 (4)	0.044 (4)	0.047 (4)	0.009 (3)	0.002 (3)	0.001 (3)
C2	0.061 (5)	0.053 (4)	0.047 (4)	0.017 (4)	0.011 (4)	0.002 (3)
C3	0.054 (5)	0.084 (6)	0.047 (4)	0.034 (4)	0.017 (4)	0.007 (4)
C4	0.036 (4)	0.064 (5)	0.054 (5)	0.010 (3)	0.002 (3)	0.004 (4)
C5	0.032 (3)	0.047 (4)	0.038 (4)	0.011 (3)	0.002 (3)	0.007 (3)
C6	0.044 (4)	0.032 (3)	0.036 (4)	0.008 (3)	0.003 (3)	0.000 (3)
C7	0.030 (4)	0.059 (4)	0.037 (4)	0.005 (3)	−0.003 (3)	0.006 (3)
C8	0.045 (4)	0.040 (4)	0.046 (4)	0.009 (3)	0.007 (3)	0.002 (3)
C9	0.046 (4)	0.053 (4)	0.061 (5)	0.025 (3)	0.010 (4)	0.012 (4)
C10	0.048 (4)	0.054 (4)	0.050 (4)	0.017 (3)	0.010 (3)	0.003 (3)
C11	0.028 (3)	0.028 (3)	0.052 (4)	0.001 (2)	0.002 (3)	0.012 (3)
C12	0.031 (4)	0.043 (4)	0.078 (5)	0.002 (3)	0.005 (4)	0.020 (4)
C13	0.043 (4)	0.054 (4)	0.082 (6)	0.023 (4)	0.031 (4)	0.032 (4)
C14	0.061 (5)	0.046 (4)	0.064 (5)	0.022 (4)	0.030 (4)	0.014 (4)
C15	0.061 (5)	0.035 (4)	0.061 (5)	0.013 (3)	0.020 (4)	0.006 (3)
C16	0.038 (3)	0.033 (3)	0.040 (4)	0.008 (3)	0.004 (3)	0.006 (3)
C17	0.028 (3)	0.041 (4)	0.044 (4)	0.005 (3)	0.000 (3)	0.005 (3)
C18	0.041 (4)	0.021 (3)	0.048 (4)	0.002 (3)	0.003 (3)	0.010 (3)
C19	0.038 (4)	0.051 (4)	0.052 (4)	0.010 (3)	0.016 (3)	0.005 (3)
C20	0.027 (3)	0.032 (3)	0.073 (5)	0.011 (3)	0.005 (3)	−0.001 (3)
C21	0.048 (4)	0.045 (4)	0.078 (6)	0.005 (3)	0.008 (4)	0.016 (4)
C22	0.058 (5)	0.058 (5)	0.069 (5)	0.027 (4)	0.026 (4)	0.021 (4)
C23	0.067 (5)	0.054 (4)	0.051 (4)	0.024 (4)	0.019 (4)	0.015 (4)
C24	0.057 (4)	0.050 (4)	0.045 (4)	0.013 (3)	0.009 (4)	0.004 (3)
C25	0.039 (4)	0.034 (3)	0.049 (4)	0.011 (3)	−0.003 (3)	0.006 (3)
C26	0.043 (4)	0.041 (4)	0.048 (4)	0.014 (3)	0.005 (3)	0.008 (3)
C27	0.048 (4)	0.040 (4)	0.051 (4)	0.007 (3)	−0.004 (3)	−0.007 (3)
C28	0.042 (4)	0.044 (4)	0.048 (4)	0.010 (3)	0.006 (3)	0.004 (3)
C29	0.070 (5)	0.059 (5)	0.060 (5)	0.023 (4)	0.020 (4)	0.006 (4)
C30	0.066 (5)	0.069 (5)	0.061 (5)	0.027 (4)	0.012 (4)	0.007 (4)
N1	0.040 (3)	0.039 (3)	0.050 (3)	0.018 (2)	0.008 (3)	0.004 (2)
N2	0.031 (3)	0.026 (2)	0.050 (3)	0.007 (2)	0.009 (2)	0.000 (2)
N3	0.050 (4)	0.041 (3)	0.058 (4)	0.012 (3)	0.009 (3)	−0.009 (3)
O1	0.060 (3)	0.050 (3)	0.080 (4)	0.001 (3)	0.005 (3)	−0.020 (3)
O2	0.045 (3)	0.078 (4)	0.083 (4)	0.006 (3)	−0.001 (3)	−0.010 (3)
O3	0.042 (3)	0.039 (3)	0.068 (3)	0.000 (2)	−0.016 (3)	−0.003 (2)
O4	0.027 (2)	0.059 (3)	0.075 (4)	0.000 (2)	−0.006 (2)	−0.017 (3)
O5	0.038 (3)	0.072 (4)	0.091 (4)	0.003 (3)	−0.001 (3)	−0.003 (3)
O6	0.074 (4)	0.057 (3)	0.094 (5)	0.008 (3)	−0.002 (3)	−0.028 (3)

Geometric parameters (Å, º) top

Br2—C10	1.955 (6)	C15—H15	0.9300
Br1—C20	1.917 (6)	C16—C17	1.490 (8)
Br3—C30	1.949 (7)	C17—O4	1.191 (7)
C1—C2	1.356 (10)	C17—N2	1.399 (8)
C1—C6	1.397 (9)	C18—O3	1.211 (7)
C1—H1	0.9300	C18—N2	1.407 (8)
C2—C3	1.381 (10)	C19—N2	1.460 (7)
C2—H2	0.9300	C19—C20	1.506 (9)
C3—C4	1.382 (10)	C19—H19A	0.9700
C3—H3	0.9300	C19—H19B	0.9700
C4—C5	1.382 (9)	C20—H20A	0.9700
C4—H4	0.9300	C20—H20B	0.9700
C5—C6	1.392 (9)	C21—C26	1.363 (10)
C5—C8	1.470 (9)	C21—C22	1.385 (10)
C6—C7	1.462 (9)	C21—H21	0.9300
C7—O2	1.199 (8)	C22—C23	1.413 (11)
C7—N1	1.418 (8)	C22—H22	0.9300
C8—O1	1.196 (8)	C23—C24	1.369 (10)
C8—N1	1.380 (8)	C23—H23	0.9300
C9—C10	1.463 (10)	C24—C25	1.360 (9)
C9—N1	1.485 (8)	C24—H24	0.9300
C9—H9A	0.9700	C25—C26	1.377 (9)
C9—H9B	0.9700	C25—C28	1.489 (9)
C10—H10A	0.9700	C26—C27	1.500 (9)
C10—H10B	0.9700	C27—O6	1.191 (8)
C11—C12	1.374 (9)	C27—N3	1.369 (9)
C11—C16	1.381 (9)	C28—O5	1.196 (8)
C11—C18	1.468 (9)	C28—N3	1.385 (8)
C12—C13	1.374 (10)	C29—N3	1.488 (9)
C12—H12	0.9300	C29—C30	1.490 (10)
C13—C14	1.368 (10)	C29—H29A	0.9700
C13—H13	0.9300	C29—H29B	0.9700
C14—C15	1.395 (10)	C30—H30A	0.9700
C14—H14	0.9300	C30—H30B	0.9700
C15—C16	1.381 (9)

Cg1···Cg4ⁱ	3.517 (4)	Cg2···Cg6	3.950 (4)
Cg1···Cg6ⁱⁱ	3.629 (4)	Cg3···Cg4^iv	3.603 (4)
Cg2···Cg5ⁱⁱⁱ	3.558 (4)	Cg3···Cg5	3.843 (4)

C2—C1—C6	116.9 (7)	N2—C18—C11	105.7 (5)
C2—C1—H1	121.6	N2—C19—C20	112.6 (5)
C6—C1—H1	121.6	N2—C19—H19A	109.1
C1—C2—C3	122.9 (7)	C20—C19—H19A	109.1
C1—C2—H2	118.6	N2—C19—H19B	109.1
C3—C2—H2	118.6	C20—C19—H19B	109.1
C2—C3—C4	120.2 (7)	H19A—C19—H19B	107.8
C2—C3—H3	119.9	C19—C20—Br1	112.4 (4)
C4—C3—H3	119.9	C19—C20—H20A	109.1
C3—C4—C5	118.6 (7)	Br1—C20—H20A	109.1
C3—C4—H4	120.7	C19—C20—H20B	109.1
C5—C4—H4	120.7	Br1—C20—H20B	109.1
C4—C5—C6	120.0 (6)	H20A—C20—H20B	107.9
C4—C5—C8	131.4 (6)	C26—C21—C22	116.9 (7)
C6—C5—C8	108.7 (5)	C26—C21—H21	121.6
C5—C6—C1	121.5 (6)	C22—C21—H21	121.6
C5—C6—C7	108.2 (5)	C21—C22—C23	121.3 (7)
C1—C6—C7	130.3 (6)	C21—C22—H22	119.4
O2—C7—N1	123.6 (6)	C23—C22—H22	119.4
O2—C7—C6	131.0 (6)	C24—C23—C22	119.5 (7)
N1—C7—C6	105.4 (5)	C24—C23—H23	120.3
O1—C8—N1	124.9 (6)	C22—C23—H23	120.3
O1—C8—C5	129.2 (6)	C25—C24—C23	119.0 (7)
N1—C8—C5	105.8 (5)	C25—C24—H24	120.5
C10—C9—N1	110.8 (6)	C23—C24—H24	120.5
C10—C9—H9A	109.5	C24—C25—C26	121.1 (6)
N1—C9—H9A	109.5	C24—C25—C28	130.4 (6)
C10—C9—H9B	109.5	C26—C25—C28	108.5 (5)
N1—C9—H9B	109.5	C21—C26—C25	122.2 (6)
H9A—C9—H9B	108.1	C21—C26—C27	130.2 (7)
C9—C10—Br2	108.9 (5)	C25—C26—C27	107.5 (6)
C9—C10—H10A	109.9	O6—C27—N3	124.8 (7)
Br2—C10—H10A	109.9	O6—C27—C26	129.5 (7)
C9—C10—H10B	109.9	N3—C27—C26	105.6 (5)
Br2—C10—H10B	109.9	O5—C28—N3	125.8 (6)
H10A—C10—H10B	108.3	O5—C28—C25	129.1 (6)
C12—C11—C16	120.2 (6)	N3—C28—C25	105.1 (6)
C12—C11—C18	130.8 (6)	N3—C29—C30	109.2 (6)
C16—C11—C18	109.0 (5)	N3—C29—H29A	109.8
C13—C12—C11	117.9 (7)	C30—C29—H29A	109.8
C13—C12—H12	121.0	N3—C29—H29B	109.8
C11—C12—H12	121.0	C30—C29—H29B	109.8
C14—C13—C12	121.6 (6)	H29A—C29—H29B	108.3
C14—C13—H13	119.2	C29—C30—Br3	107.4 (5)
C12—C13—H13	119.2	C29—C30—H30A	110.2
C13—C14—C15	121.9 (7)	Br3—C30—H30A	110.2
C13—C14—H14	119.0	C29—C30—H30B	110.2
C15—C14—H14	119.0	Br3—C30—H30B	110.2
C16—C15—C14	115.4 (7)	H30A—C30—H30B	108.5
C16—C15—H15	122.3	C8—N1—C7	111.9 (5)
C14—C15—H15	122.3	C8—N1—C9	125.3 (5)
C15—C16—C11	123.0 (6)	C7—N1—C9	122.6 (5)
C15—C16—C17	128.8 (6)	C17—N2—C18	111.7 (5)
C11—C16—C17	108.1 (5)	C17—N2—C19	123.9 (5)
O4—C17—N2	123.9 (6)	C18—N2—C19	124.1 (5)
O4—C17—C16	130.7 (6)	C27—N3—C28	113.3 (6)
N2—C17—C16	105.5 (5)	C27—N3—C29	123.9 (6)
O3—C18—N2	123.8 (6)	C28—N3—C29	122.4 (6)
O3—C18—C11	130.5 (6)

C6—C1—C2—C3	−2.2 (11)	C22—C21—C26—C25	−1.4 (11)
C1—C2—C3—C4	0.9 (12)	C22—C21—C26—C27	−178.0 (7)
C2—C3—C4—C5	0.5 (11)	C24—C25—C26—C21	0.6 (11)
C3—C4—C5—C6	−0.4 (11)	C28—C25—C26—C21	−179.5 (7)
C3—C4—C5—C8	−179.7 (7)	C24—C25—C26—C27	177.9 (6)
C4—C5—C6—C1	−1.0 (10)	C28—C25—C26—C27	−2.2 (8)
C8—C5—C6—C1	178.4 (6)	C21—C26—C27—O6	−2.9 (14)
C4—C5—C6—C7	−179.9 (6)	C25—C26—C27—O6	−179.9 (8)
C8—C5—C6—C7	−0.5 (7)	C21—C26—C27—N3	179.4 (8)
C2—C1—C6—C5	2.2 (10)	C25—C26—C27—N3	2.4 (8)
C2—C1—C6—C7	−179.0 (7)	C24—C25—C28—O5	2.0 (13)
C5—C6—C7—O2	179.6 (8)	C26—C25—C28—O5	−177.9 (8)
C1—C6—C7—O2	0.8 (13)	C24—C25—C28—N3	−178.9 (7)
C5—C6—C7—N1	0.3 (7)	C26—C25—C28—N3	1.2 (8)
C1—C6—C7—N1	−178.5 (7)	N3—C29—C30—Br3	−179.8 (5)
C4—C5—C8—O1	1.1 (14)	O1—C8—N1—C7	178.5 (7)
C6—C5—C8—O1	−178.2 (7)	C5—C8—N1—C7	−0.3 (8)
C4—C5—C8—N1	179.8 (7)	O1—C8—N1—C9	2.3 (12)
C6—C5—C8—N1	0.5 (8)	C5—C8—N1—C9	−176.5 (6)
N1—C9—C10—Br2	−179.4 (4)	O2—C7—N1—C8	−179.3 (7)
C16—C11—C12—C13	0.8 (10)	C6—C7—N1—C8	0.0 (7)
C18—C11—C12—C13	177.9 (6)	O2—C7—N1—C9	−3.1 (11)
C11—C12—C13—C14	−0.5 (11)	C6—C7—N1—C9	176.3 (6)
C12—C13—C14—C15	−0.2 (11)	C10—C9—N1—C8	−96.1 (8)
C13—C14—C15—C16	0.6 (11)	C10—C9—N1—C7	88.1 (8)
C14—C15—C16—C11	−0.3 (10)	O4—C17—N2—C18	177.6 (6)
C14—C15—C16—C17	−177.0 (6)	C16—C17—N2—C18	−2.4 (7)
C12—C11—C16—C15	−0.4 (10)	O4—C17—N2—C19	4.2 (10)
C18—C11—C16—C15	−178.1 (6)	C16—C17—N2—C19	−175.8 (6)
C12—C11—C16—C17	176.9 (6)	O3—C18—N2—C17	−176.3 (6)
C18—C11—C16—C17	−0.7 (7)	C11—C18—N2—C17	2.0 (7)
C15—C16—C17—O4	−1.0 (12)	O3—C18—N2—C19	−2.9 (9)
C11—C16—C17—O4	−178.1 (7)	C11—C18—N2—C19	175.3 (6)
C15—C16—C17—N2	179.0 (6)	C20—C19—N2—C17	−78.0 (8)
C11—C16—C17—N2	1.9 (7)	C20—C19—N2—C18	109.4 (7)
C12—C11—C18—O3	0.1 (12)	O6—C27—N3—C28	−179.5 (8)
C16—C11—C18—O3	177.4 (6)	C26—C27—N3—C28	−1.7 (8)
C12—C11—C18—N2	−178.0 (7)	O6—C27—N3—C29	8.0 (13)
C16—C11—C18—N2	−0.7 (7)	C26—C27—N3—C29	−174.2 (6)
N2—C19—C20—Br1	−66.5 (6)	O5—C28—N3—C27	179.6 (7)
C26—C21—C22—C23	1.9 (11)	C25—C28—N3—C27	0.4 (8)
C21—C22—C23—C24	−1.6 (11)	O5—C28—N3—C29	−7.8 (12)
C22—C23—C24—C25	0.7 (11)	C25—C28—N3—C29	173.1 (6)
C23—C24—C25—C26	−0.2 (11)	C30—C29—N3—C27	−93.1 (9)
C23—C24—C25—C28	179.9 (7)	C30—C29—N3—C28	95.1 (8)

Symmetry codes: (i) −x+1, −y, −z; (ii) x, y−1, z; (iii) −x+1, −y+1, −z+1; (iv) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O6ⁱ	0.93	2.59	3.301 (9)	133
C10—H10A···O3ⁱⁱⁱ	0.97	2.48	3.409 (8)	161
C10—H10B···O5^v	0.97	2.60	3.533 (9)	163
C13—H13···O4^vi	0.93	2.52	3.448 (8)	175
C14—H14···O1	0.93	2.59	3.495 (10)	165

Symmetry codes: (i) −x+1, −y, −z; (iii) −x+1, −y+1, −z+1; (v) x−1, y−1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₀H₈BrNO₂
M_r	254.08
Crystal system, space group	Triclinic, P1
Temperature (K)	297
a, b, c (Å)	8.575 (2), 11.067 (3), 16.333 (5)
α, β, γ (°)	99.001 (6), 96.164 (5), 102.259 (6)
V (Å³)	1480.2 (7)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	4.14
Crystal size (mm)	0.25 × 0.23 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.370, 0.437
No. of measured, independent and observed [I > 2σ(I)] reflections	7716, 5043, 3241
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.177, 1.00
No. of reflections	5043
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.64

Computer programs: APEX2 (Bruker, 2000), SAINT (Bruker, 2000), 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
C2—H2···O6ⁱ	0.93	2.593	3.301 (9)	133
C10—H10A···O3ⁱⁱ	0.97	2.476	3.409 (8)	161
C10—H10B···O5ⁱⁱⁱ	0.97	2.596	3.533 (9)	163
C13—H13···O4^iv	0.93	2.521	3.448 (8)	175
C14—H14···O1	0.93	2.590	3.495 (10)	165

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z+1; (iii) x−1, y−1, z; (iv) x+1, y, z.

Acknowledgements

We gratefully acknowledge Changzhou University and the Key Laboratory of Fine Chemical Engineering of Jiangsu Province for financial support (ZMF10020010 and SCZ10102271B).

References

Bruker (2000). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Clouet, G. & Juhl, H. J. (1994). Macromol. Chem. Phys. 195, 243–251. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheng, X., Lu, X.-M., Zhang, J.-J., Chen, Y.-T., Lu, G.-Y., Shao, Y., Liu, F. & Xu, Q. (2007). J. Org. Chem. 72, 1799–1802. Web of Science CrossRef PubMed CAS Google Scholar