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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2416.
Published online 2008 November 22. doi:  10.1107/S1600536808038166
PMCID: PMC2960063

Ethane-1,2-diaminium 3,4,5,6-tetra­bromo-2-(methoxy­carbon­yl)benzoate methanol solvate

Abstract

In the title compound, C2H10N2 2+·2C9H3Br4O4 ·CH4O, the N atoms of the ethane-1,2-diamine mol­ecule are protonated. The crystal structure is stabilized by N—H(...)O hydrogen bonds between the ethane-1,2-diaminium cations and 3,4,5,6-tetra­bromo-2-(methoxy­carbon­yl)bromo­benzoate anions, and by O—H(...)O and N—H(...)O hydrogen bonds between the methanol solvate and both the cation and the anion. In addition, the crystal structure exhibits a C—Br(...)O halogen bond [3.20 (3) Å] and a Br(...)Br inter­action [3.560 (2) Å].

Related literature

For related structures, see: Liang et al. (2006 [triangle], 2007 [triangle]); For a review of halogen bonding, see: Politzer et al. (2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2416-scheme1.jpg

Experimental

Crystal data

  • C2H10N2 2+·2C9H3Br4O4 ·CH4O
  • M r = 1083.67
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2416-efi5.jpg
  • a = 6.456 (2) Å
  • b = 19.036 (7) Å
  • c = 26.017 (9) Å
  • β = 96.002 (6)°
  • V = 3179.7 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 10.14 mm−1
  • T = 298 (2) K
  • 0.41 × 0.25 × 0.15 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.062, T max = 0.221
  • 15827 measured reflections
  • 5585 independent reflections
  • 3448 reflections with I > 2σ(I)
  • R int = 0.083

Refinement

  • R[F 2 > 2σ(F 2)] = 0.055
  • wR(F 2) = 0.145
  • S = 0.98
  • 5585 reflections
  • 367 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 1.18 e Å−3
  • Δρmin = −0.72 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]) and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038166/lx2065sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038166/lx2065Isup2.hkl

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

Acknowledgments

This work was supported by the Natural Science Foundation of Shandong Province (grant No. Y2007B61).

supplementary crystallographic information

Comment

1,2-Bis(tetrabromophthalimido)ethane is an important flame retardant. 2-(Methoxycarbonyl)-3,4,5,6-tetrabromobenzoic acid is the intermediate of the flame retardant. In this paper, the structure of the title compound is reported.

The asymmetric unit of the title compound contains one ethane-1,2-diaminium, two 3,4,5,6-tetrabromo-2-(methoxycarbonyl)bromobenzoate and one methanol molecule (Fig. 1). The bond lengths and angles agree with those in those similar compounds 4-phthalimidobenzoic acid N,N-dimethylformamide solvate (Liang et al., 2006) and 4-(5-Bromo-1,3-dioxoisoindolin-2-yl)benzoic acid N,N-dimethylformamide solvate (Liang et al., 2007). The dihedral angle between two benzene rings is 74.6 (2)°.

The crystal structure is stabilized by various hydrogen bonds (Fig. 2 and Table 1; symmetry code as in Fig. 2); N—H···O hydrogen bonds between the ethane-1,2-diaminium and the 2-(methoxycarbonyl)-3,4,5,6-tetrabromobenzoate anions, O—H···O and N—H···O hydrogen bonds between the methanol and the 3,4,5,6-tetrabromo-2-(methoxycarbonyl)bromobenzoate anions and the ethane-1,2-diaminium. The further stability comes from a weak C—Br···O halogen bond (Fig. 2) (Politzer et al., 2007); between the bromine atom and the oxygen of a neighbouring methoxy group, i.e. C13—Br8···O4v distance of 3.20 (3) Å and a C13—Br8···O4v angle of 156.9 (3)°, and a Br2···Br6vi interaction at 3.560 (2) Å (Fig. 2).

Experimental

A mixture of 4,5,6,7-tetrabromoisobenzofuran-1,3-dione (46.4 g, 0.1 mol) and methanol (150 ml) was refluxed for 0.5 h. And then ethane-1,2-diamine (3 g, 0.05 mol) was added to the above solution, being mixed round for 4 h at room temperature. After filtration and the filtrate was kept at room temperature for 3 d. Natural evaporation gave colourless single crystals of the title compound, suitable for X-ray analysis.

Refinement

H atoms were initially located from difference maps and then refined in a riding model with C—H = 0.93–0.96 Å, N—H = 0.89 Å and Uiso(H) = 1.2Ueq(C, N) or 1.5Ueq(O, methyl C).

Figures

Fig. 1.
The molecular structure of (I), drawn with 30% probability ellipsoids.
Fig. 2.
The crystal packing of (I), viewed along a axis. Hydrogen bonds are indicated by dashed lines. [Symmetry code: (i) -x + 2, y - 1/2, -z + 1/2; (ii) -x + 2, -y + 1, -z + 1; (iii) -x + 1, y - 1/2, -z + 1/2; (iv) -x + 1, -y + 1, -z + 1; (v) x - 1, y, z; (vi) ...

Crystal data

C2H10N22+·2C9H3Br4O4·CH4OF000 = 2048
Mr = 1083.67Dx = 2.264 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2716 reflections
a = 6.456 (2) Åθ = 2.3–22.1º
b = 19.036 (7) ŵ = 10.14 mm1
c = 26.017 (9) ÅT = 298 (2) K
β = 96.002 (6)ºBlock, colourless
V = 3179.7 (19) Å30.41 × 0.25 × 0.15 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer5585 independent reflections
Radiation source: fine-focus sealed tube3448 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.083
Detector resolution: 10.0 pixels mm-1θmax = 25.0º
T = 298(2) Kθmin = 1.6º
[var phi] and ω scansh = −7→6
Absorption correction: multi-scan(SADABS; Bruker, 1997)k = −22→22
Tmin = 0.062, Tmax = 0.221l = −30→25
15827 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.055H-atom parameters constrained
wR(F2) = 0.145  w = 1/[σ2(Fo2) + (0.0474P)2] where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
5585 reflectionsΔρmax = 1.18 e Å3
367 parametersΔρmin = −0.72 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/Ueq
C130.2706 (12)0.7587 (4)0.4305 (3)0.028 (2)
Br50.90144 (14)0.74383 (5)0.53528 (4)0.0387 (3)
Br80.01592 (15)0.76205 (5)0.38806 (4)0.0515 (3)
Br70.18589 (16)0.89882 (5)0.45626 (4)0.0508 (3)
Br11.30682 (16)1.00363 (5)0.23756 (4)0.0488 (3)
Br60.64413 (16)0.89277 (5)0.52383 (4)0.0473 (3)
Br30.7771 (2)1.01282 (6)0.39936 (4)0.0712 (4)
Br40.52006 (19)0.87733 (7)0.34731 (5)0.0694 (4)
Br21.1722 (2)1.07590 (7)0.34433 (5)0.0789 (4)
O50.7309 (8)0.5905 (3)0.5074 (2)0.0316 (14)
O60.7401 (9)0.6008 (3)0.4220 (2)0.0355 (15)
O20.9487 (9)0.9138 (3)0.1572 (2)0.0366 (15)
O90.2812 (10)0.7719 (3)0.1141 (2)0.0387 (15)
H90.25280.79170.14050.058*
C150.5347 (13)0.8125 (4)0.4890 (3)0.029 (2)
N10.9242 (10)0.4714 (3)0.4311 (2)0.0295 (17)
H1A0.96670.45970.40080.044*
H1B1.02830.46550.45590.044*
H1C0.88410.51610.43030.044*
C140.3451 (13)0.8158 (4)0.4590 (3)0.027 (2)
C40.7531 (14)0.9129 (5)0.3182 (3)0.040 (2)
C50.8078 (13)0.8814 (4)0.2718 (3)0.031 (2)
C110.3057 (13)0.6319 (5)0.4029 (3)0.031 (2)
O11.1336 (11)0.8281 (3)0.1981 (2)0.0498 (18)
C160.6458 (12)0.7499 (4)0.4910 (3)0.0247 (18)
C190.5754 (12)0.4323 (4)0.3977 (3)0.029 (2)
H19A0.50670.47750.39950.035*
H19B0.63390.42950.36490.035*
C170.5723 (12)0.6915 (4)0.4644 (3)0.0234 (19)
N20.4214 (10)0.3748 (3)0.4012 (2)0.0307 (17)
H2A0.48090.33370.39560.046*
H2B0.31320.38150.37760.046*
H2C0.37790.37480.43260.046*
O40.7137 (11)0.7667 (3)0.2822 (3)0.059 (2)
C180.6933 (12)0.6221 (4)0.4644 (3)0.0236 (19)
O30.6344 (11)0.8134 (4)0.2056 (3)0.061 (2)
C11.0757 (13)0.9683 (5)0.2702 (3)0.034 (2)
C60.9726 (13)0.9107 (4)0.2478 (3)0.0260 (19)
C120.3863 (12)0.6964 (4)0.4321 (3)0.0212 (18)
C71.0268 (14)0.8808 (5)0.1962 (3)0.030 (2)
O70.2565 (9)0.5792 (3)0.4236 (2)0.0381 (15)
O80.2970 (10)0.6420 (3)0.3525 (2)0.0475 (17)
C80.7027 (14)0.8161 (5)0.2485 (4)0.039 (2)
C21.0236 (15)0.9986 (5)0.3156 (3)0.039 (2)
C30.8613 (17)0.9711 (5)0.3390 (4)0.046 (3)
C200.7472 (12)0.4262 (4)0.4415 (3)0.029 (2)
H20A0.69560.44040.47360.035*
H20B0.79290.37770.44500.035*
C210.3236 (18)0.7007 (5)0.1248 (4)0.059 (3)
H21A0.45470.69660.14570.089*
H21B0.33000.67570.09300.089*
H21C0.21530.68130.14310.089*
C100.192 (2)0.5888 (6)0.3205 (4)0.077 (4)
H10A0.25800.54420.32790.116*
H10B0.19820.60040.28480.116*
H10C0.04880.58610.32740.116*
C90.605 (3)0.7038 (7)0.2652 (5)0.112 (6)
H9A0.47930.71600.24400.169*
H9B0.57080.67760.29460.169*
H9C0.69190.67590.24550.169*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C130.026 (5)0.040 (5)0.017 (4)0.004 (4)−0.001 (3)0.010 (4)
Br50.0371 (5)0.0371 (6)0.0384 (6)−0.0028 (4)−0.0124 (4)−0.0011 (4)
Br80.0390 (6)0.0536 (7)0.0570 (7)0.0077 (5)−0.0170 (5)0.0117 (5)
Br70.0594 (7)0.0334 (6)0.0609 (7)0.0211 (5)0.0124 (5)0.0069 (5)
Br10.0489 (6)0.0493 (6)0.0484 (7)−0.0134 (5)0.0065 (5)−0.0022 (5)
Br60.0684 (7)0.0281 (5)0.0453 (6)−0.0054 (5)0.0055 (5)−0.0119 (5)
Br30.1170 (11)0.0641 (8)0.0366 (6)0.0414 (7)0.0267 (6)0.0001 (6)
Br40.0671 (8)0.0844 (9)0.0636 (8)0.0141 (6)0.0398 (6)0.0286 (7)
Br20.1045 (11)0.0677 (8)0.0625 (8)−0.0110 (7)−0.0005 (7)−0.0366 (7)
O50.038 (4)0.032 (3)0.025 (3)0.006 (3)0.003 (3)0.004 (3)
O60.050 (4)0.026 (3)0.032 (4)0.010 (3)0.011 (3)−0.001 (3)
O20.046 (4)0.047 (4)0.017 (3)−0.008 (3)0.003 (3)0.009 (3)
O90.053 (4)0.026 (3)0.036 (4)−0.003 (3)0.005 (3)−0.002 (3)
C150.044 (6)0.022 (5)0.023 (5)0.004 (4)0.008 (4)0.000 (4)
N10.037 (4)0.029 (4)0.023 (4)0.005 (3)0.007 (3)−0.004 (3)
C140.034 (5)0.023 (5)0.023 (5)0.011 (4)0.008 (4)0.005 (4)
C40.037 (6)0.059 (7)0.027 (5)0.022 (5)0.012 (4)0.023 (5)
C50.033 (5)0.041 (6)0.021 (5)0.008 (4)0.006 (4)0.013 (4)
C110.034 (5)0.037 (6)0.023 (5)−0.002 (4)−0.001 (4)0.001 (4)
O10.065 (5)0.046 (4)0.039 (4)0.025 (4)0.006 (3)−0.006 (3)
C160.028 (4)0.028 (5)0.017 (4)0.000 (4)0.001 (3)0.003 (4)
C190.037 (5)0.021 (5)0.030 (5)0.001 (4)0.005 (4)0.006 (4)
C170.027 (5)0.021 (5)0.023 (5)0.003 (3)0.006 (4)0.001 (4)
N20.033 (4)0.035 (4)0.022 (4)0.000 (3)−0.003 (3)0.001 (3)
O40.078 (5)0.043 (4)0.055 (5)−0.021 (4)0.000 (4)0.012 (4)
C180.022 (4)0.022 (5)0.026 (5)−0.002 (3)−0.002 (4)0.000 (4)
O30.061 (5)0.083 (6)0.038 (4)−0.036 (4)0.002 (4)−0.001 (4)
C10.034 (5)0.046 (6)0.023 (5)0.009 (4)0.004 (4)0.008 (4)
C60.037 (5)0.024 (5)0.016 (4)0.009 (4)−0.002 (4)0.001 (4)
C120.028 (5)0.014 (4)0.022 (5)0.000 (3)0.003 (4)0.003 (3)
C70.037 (5)0.034 (5)0.021 (5)−0.013 (4)0.008 (4)−0.008 (4)
O70.048 (4)0.026 (3)0.038 (4)−0.004 (3)−0.001 (3)0.009 (3)
O80.069 (5)0.044 (4)0.026 (4)−0.011 (3)−0.011 (3)−0.003 (3)
C80.039 (5)0.053 (5)0.025 (4)−0.005 (4)0.013 (4)0.023 (4)
C20.051 (6)0.040 (6)0.025 (5)0.009 (5)−0.003 (4)−0.007 (5)
C30.064 (7)0.043 (6)0.029 (6)0.018 (5)0.000 (5)0.004 (5)
C200.034 (5)0.037 (5)0.015 (4)0.002 (4)0.001 (4)−0.006 (4)
C210.096 (9)0.028 (6)0.052 (7)−0.001 (6)0.001 (6)−0.007 (5)
C100.114 (11)0.071 (9)0.040 (7)−0.029 (7)−0.024 (7)−0.014 (6)
C90.174 (17)0.064 (9)0.097 (11)−0.052 (10)0.006 (10)0.011 (8)

Geometric parameters (Å, °)

C13—C141.375 (11)C16—C171.369 (10)
C13—C121.400 (10)C19—N21.489 (10)
C13—Br81.883 (8)C19—C201.509 (10)
Br5—C161.915 (8)C19—H19A0.9700
Br7—C141.882 (7)C19—H19B0.9700
Br1—C11.914 (9)C17—C121.394 (11)
Br6—C151.877 (8)C17—C181.533 (11)
Br3—C31.891 (10)N2—H2A0.8900
Br4—C41.880 (9)N2—H2B0.8900
Br2—C21.869 (9)N2—H2C0.8900
O5—C181.272 (9)O4—C81.284 (10)
O6—C181.240 (9)O4—C91.434 (13)
O2—C71.253 (10)O3—C81.158 (10)
O9—C211.404 (10)C1—C61.381 (11)
O9—H90.8200C1—C21.387 (12)
C15—C141.382 (11)C6—C71.532 (11)
C15—C161.389 (10)O8—C101.436 (10)
N1—C201.478 (10)C2—C31.369 (13)
N1—H1A0.8900C20—H20A0.9700
N1—H1B0.8900C20—H20B0.9700
N1—H1C0.8900C21—H21A0.9600
C4—C31.388 (13)C21—H21B0.9600
C4—C51.424 (12)C21—H21C0.9600
C5—C61.405 (11)C10—H10A0.9600
C5—C81.512 (13)C10—H10B0.9600
C11—O71.197 (9)C10—H10C0.9600
C11—O81.321 (10)C9—H9A0.9600
C11—C121.506 (11)C9—H9B0.9600
O1—C71.215 (10)C9—H9C0.9600
?···??
C14—C13—C12119.9 (7)C6—C1—C2122.7 (8)
C14—C13—Br8121.6 (6)C6—C1—Br1117.1 (6)
C12—C13—Br8118.5 (6)C2—C1—Br1120.1 (7)
C21—O9—H9109.5C1—C6—C5118.8 (8)
C14—C15—C16118.9 (7)C1—C6—C7121.4 (8)
C14—C15—Br6120.1 (6)C5—C6—C7119.7 (7)
C16—C15—Br6120.9 (6)C17—C12—C13119.9 (7)
C20—N1—H1A109.5C17—C12—C11118.6 (7)
C20—N1—H1B109.5C13—C12—C11121.3 (7)
H1A—N1—H1B109.5O1—C7—O2128.7 (8)
C20—N1—H1C109.5O1—C7—C6116.8 (8)
H1A—N1—H1C109.5O2—C7—C6114.4 (8)
H1B—N1—H1C109.5C11—O8—C10116.3 (8)
C13—C14—C15120.5 (7)O3—C8—O4127.9 (10)
C13—C14—Br7119.0 (6)O3—C8—C5122.3 (8)
C15—C14—Br7120.5 (6)O4—C8—C5109.6 (8)
C3—C4—C5120.4 (9)C3—C2—C1119.0 (9)
C3—C4—Br4121.5 (7)C3—C2—Br2120.5 (7)
C5—C4—Br4118.0 (8)C1—C2—Br2120.5 (8)
C6—C5—C4118.5 (8)C2—C3—C4120.6 (9)
C6—C5—C8118.4 (7)C2—C3—Br3120.6 (8)
C4—C5—C8123.1 (8)C4—C3—Br3118.8 (8)
O7—C11—O8125.6 (8)N1—C20—C19109.7 (6)
O7—C11—C12123.4 (8)N1—C20—H20A109.7
O8—C11—C12111.0 (7)C19—C20—H20A109.7
C17—C16—C15121.9 (7)N1—C20—H20B109.7
C17—C16—Br5119.1 (6)C19—C20—H20B109.7
C15—C16—Br5118.9 (6)H20A—C20—H20B108.2
N2—C19—C20109.9 (6)O9—C21—H21A109.5
N2—C19—H19A109.7O9—C21—H21B109.5
C20—C19—H19A109.7H21A—C21—H21B109.5
N2—C19—H19B109.7O9—C21—H21C109.5
C20—C19—H19B109.7H21A—C21—H21C109.5
H19A—C19—H19B108.2H21B—C21—H21C109.5
C16—C17—C12118.8 (7)O8—C10—H10A109.5
C16—C17—C18123.3 (7)O8—C10—H10B109.5
C12—C17—C18117.7 (7)H10A—C10—H10B109.5
C19—N2—H2A109.5O8—C10—H10C109.5
C19—N2—H2B109.5H10A—C10—H10C109.5
H2A—N2—H2B109.5H10B—C10—H10C109.5
C19—N2—H2C109.5O4—C9—H9A109.5
H2A—N2—H2C109.5O4—C9—H9B109.5
H2B—N2—H2C109.5H9A—C9—H9B109.5
C8—O4—C9114.2 (9)O4—C9—H9C109.5
O6—C18—O5125.7 (7)H9A—C9—H9C109.5
O6—C18—C17117.0 (7)H9B—C9—H9C109.5
O5—C18—C17117.2 (7)
C12—C13—C14—C150.6 (12)C18—C17—C12—C115.4 (11)
Br8—C13—C14—C15−178.6 (6)C14—C13—C12—C172.8 (12)
C12—C13—C14—Br7−179.8 (6)Br8—C13—C12—C17−178.0 (6)
Br8—C13—C14—Br71.0 (9)C14—C13—C12—C11177.7 (7)
C16—C15—C14—C13−1.9 (12)Br8—C13—C12—C11−3.1 (10)
Br6—C15—C14—C13175.4 (6)O7—C11—C12—C1762.5 (11)
C16—C15—C14—Br7178.6 (6)O8—C11—C12—C17−117.7 (8)
Br6—C15—C14—Br7−4.1 (10)O7—C11—C12—C13−112.4 (10)
C3—C4—C5—C6−0.2 (12)O8—C11—C12—C1367.4 (10)
Br4—C4—C5—C6175.6 (6)C1—C6—C7—O1101.9 (10)
C3—C4—C5—C8177.3 (8)C5—C6—C7—O1−81.3 (10)
Br4—C4—C5—C8−6.9 (11)C1—C6—C7—O2−79.9 (10)
C14—C15—C16—C17−0.3 (13)C5—C6—C7—O296.9 (9)
Br6—C15—C16—C17−177.6 (6)O7—C11—O8—C109.4 (13)
C14—C15—C16—Br5−176.8 (6)C12—C11—O8—C10−170.4 (8)
Br6—C15—C16—Br55.9 (9)C9—O4—C8—O3−8.1 (16)
C15—C16—C17—C123.7 (12)C9—O4—C8—C5175.6 (10)
Br5—C16—C17—C12−179.8 (6)C6—C5—C8—O3−54.1 (13)
C15—C16—C17—C18178.1 (8)C4—C5—C8—O3128.5 (10)
Br5—C16—C17—C18−5.4 (11)C6—C5—C8—O4122.5 (8)
C16—C17—C18—O6−119.1 (9)C4—C5—C8—O4−55.0 (11)
C12—C17—C18—O655.3 (10)C6—C1—C2—C3−1.0 (13)
C16—C17—C18—O563.1 (11)Br1—C1—C2—C3−178.1 (7)
C12—C17—C18—O5−122.5 (8)C6—C1—C2—Br2179.1 (6)
C2—C1—C6—C50.1 (12)Br1—C1—C2—Br22.0 (10)
Br1—C1—C6—C5177.3 (6)C1—C2—C3—C41.3 (14)
C2—C1—C6—C7176.9 (8)Br2—C2—C3—C4−178.8 (6)
Br1—C1—C6—C7−5.9 (10)C1—C2—C3—Br3−177.4 (6)
C4—C5—C6—C10.5 (12)Br2—C2—C3—Br32.4 (11)
C8—C5—C6—C1−177.1 (7)C5—C4—C3—C2−0.7 (13)
C4—C5—C6—C7−176.4 (7)Br4—C4—C3—C2−176.4 (7)
C8—C5—C6—C76.0 (12)C5—C4—C3—Br3178.0 (6)
C16—C17—C12—C13−4.9 (12)Br4—C4—C3—Br32.4 (10)
C18—C17—C12—C13−179.6 (7)N2—C19—C20—N1166.0 (6)
C16—C17—C12—C11−179.9 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.891.872.748 (8)167
N1—H1B···O5ii0.892.042.857 (8)153
N1—H1C···O60.891.862.734 (8)166
N2—H2A···O9iii0.891.972.801 (9)154
N2—H2B···O2iii0.891.932.795 (9)163
N2—H2B···O3iii0.892.573.000 (9)110
N2—H2C···O5iv0.891.902.747 (9)159
O9—H9···O1v0.821.892.695 (8)168

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) −x+2, −y+1, −z+1; (iii) −x+1, y−1/2, −z+1/2; (iv) −x+1, −y+1, −z+1; (v) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LX2065).

References

  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (1997). SADABS, SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Liang, Z.-P., Li, J. & Huang, B.-Y. (2006). Acta Cryst. E62, o4761–o4762.
  • Liang, Z.-P., Li, J., Hua, Y. & Wang, H.-L. (2007). Acta Cryst. E63, o3065.
  • Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model.13, 305–11. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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