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ISSN: 2056-9890

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

aDepartment of Chemistry and Chemical Engineering, Weifang University, Weifang 261061, People's Republic of China
*Correspondence e-mail: zupeiliang@163.com

(Received 12 July 2008; accepted 17 November 2008; online 22 November 2008)

In the title compound, C2H10N22+·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[Liang, Z.-P., Li, J. & Huang, B.-Y. (2006). Acta Cryst. E62, o4761-o4762.], 2007[Liang, Z.-P., Li, J., Hua, Y. & Wang, H.-L. (2007). Acta Cryst. E63, o3065.]); For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-11.]).

[Scheme 1]

Experimental

Crystal data
  • C2H10N22+·2C9H3Br4O4·CH4O

  • Mr = 1083.67

  • Monoclinic, P 21 /c

  • 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[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.062, Tmax = 0.221

  • 15827 measured reflections

  • 5585 independent reflections

  • 3448 reflections with I > 2σ(I)

  • Rint = 0.083

Refinement
  • R[F2 > 2σ(F2)] = 0.055

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O2i 0.89 1.87 2.748 (8) 167
N1—H1B⋯O5ii 0.89 2.04 2.857 (8) 153
N1—H1C⋯O6 0.89 1.86 2.734 (8) 166
N2—H2A⋯O9iii 0.89 1.97 2.801 (9) 154
N2—H2B⋯O2iii 0.89 1.93 2.795 (9) 163
N2—H2B⋯O3iii 0.89 2.57 3.000 (9) 110
N2—H2C⋯O5iv 0.89 1.90 2.747 (9) 159
O9—H9⋯O1v 0.82 1.89 2.695 (8) 168
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y+1, -z+1; (iii) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+1; (v) x-1, y, z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), drawn with 30% probability ellipsoids.
[Figure 2] 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) -x + 1, -y + 2, -z + 1.]
Ethane-1,2-diaminium 3,4,5,6-tetrabromo-2-(methoxycarbonyl)benzoate methanol solvate top
Crystal data top
C2H10N22+·2C9H3Br4O4·CH4OF(000) = 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 = 2.3–22.1°
b = 19.036 (7) ŵ = 10.14 mm1
c = 26.017 (9) ÅT = 298 K
β = 96.002 (6)°Block, colourless
V = 3179.7 (19) Å30.41 × 0.25 × 0.15 mm
Z = 4
Data collection top
Bruker SMART CCD area-detector
diffractometer
5585 independent reflections
Radiation source: fine-focus sealed tube3448 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.083
Detector resolution: 10.0 pixels mm-1θmax = 25.0°, θmin = 1.6°
ϕ and ω scansh = 76
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
k = 2222
Tmin = 0.062, Tmax = 0.221l = 3025
15827 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145H-atom parameters constrained
S = 0.98 w = 1/[σ2(Fo2) + (0.0474P)2]
where P = (Fo2 + 2Fc2)/3
5585 reflections(Δ/σ)max < 0.001
367 parametersΔρmax = 1.18 e Å3
6 restraintsΔρmin = 0.72 e Å3
Crystal data top
C2H10N22+·2C9H3Br4O4·CH4OV = 3179.7 (19) Å3
Mr = 1083.67Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.456 (2) ŵ = 10.14 mm1
b = 19.036 (7) ÅT = 298 K
c = 26.017 (9) Å0.41 × 0.25 × 0.15 mm
β = 96.002 (6)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
5585 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)
3448 reflections with I > 2σ(I)
Tmin = 0.062, Tmax = 0.221Rint = 0.083
15827 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0556 restraints
wR(F2) = 0.145H-atom parameters constrained
S = 0.98Δρmax = 1.18 e Å3
5585 reflectionsΔρmin = 0.72 e Å3
367 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
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) top
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, º) top
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—C15178.6 (6)C14—C13—C12—C172.8 (12)
C12—C13—C14—Br7179.8 (6)Br8—C13—C12—C17178.0 (6)
Br8—C13—C14—Br71.0 (9)C14—C13—C12—C11177.7 (7)
C16—C15—C14—C131.9 (12)Br8—C13—C12—C113.1 (10)
Br6—C15—C14—C13175.4 (6)O7—C11—C12—C1762.5 (11)
C16—C15—C14—Br7178.6 (6)O8—C11—C12—C17117.7 (8)
Br6—C15—C14—Br74.1 (10)O7—C11—C12—C13112.4 (10)
C3—C4—C5—C60.2 (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—O181.3 (10)
Br4—C4—C5—C86.9 (11)C1—C6—C7—O279.9 (10)
C14—C15—C16—C170.3 (13)C5—C6—C7—O296.9 (9)
Br6—C15—C16—C17177.6 (6)O7—C11—O8—C109.4 (13)
C14—C15—C16—Br5176.8 (6)C12—C11—O8—C10170.4 (8)
Br6—C15—C16—Br55.9 (9)C9—O4—C8—O38.1 (16)
C15—C16—C17—C123.7 (12)C9—O4—C8—C5175.6 (10)
Br5—C16—C17—C12179.8 (6)C6—C5—C8—O354.1 (13)
C15—C16—C17—C18178.1 (8)C4—C5—C8—O3128.5 (10)
Br5—C16—C17—C185.4 (11)C6—C5—C8—O4122.5 (8)
C16—C17—C18—O6119.1 (9)C4—C5—C8—O455.0 (11)
C12—C17—C18—O655.3 (10)C6—C1—C2—C31.0 (13)
C16—C17—C18—O563.1 (11)Br1—C1—C2—C3178.1 (7)
C12—C17—C18—O5122.5 (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—C4178.8 (6)
Br1—C1—C6—C75.9 (10)C1—C2—C3—Br3177.4 (6)
C4—C5—C6—C10.5 (12)Br2—C2—C3—Br32.4 (11)
C8—C5—C6—C1177.1 (7)C5—C4—C3—C20.7 (13)
C4—C5—C6—C7176.4 (7)Br4—C4—C3—C2176.4 (7)
C8—C5—C6—C76.0 (12)C5—C4—C3—Br3178.0 (6)
C16—C17—C12—C134.9 (12)Br4—C4—C3—Br32.4 (10)
C18—C17—C12—C13179.6 (7)N2—C19—C20—N1166.0 (6)
C16—C17—C12—C11179.9 (7)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+1/2; (ii) x+2, y+1, z+1; (iii) x+1, y1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x1, y, z.

Experimental details

Crystal data
Chemical formulaC2H10N22+·2C9H3Br4O4·CH4O
Mr1083.67
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)6.456 (2), 19.036 (7), 26.017 (9)
β (°) 96.002 (6)
V3)3179.7 (19)
Z4
Radiation typeMo Kα
µ (mm1)10.14
Crystal size (mm)0.41 × 0.25 × 0.15
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 1997)
Tmin, Tmax0.062, 0.221
No. of measured, independent and
observed [I > 2σ(I)] reflections
15827, 5585, 3448
Rint0.083
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.145, 0.98
No. of reflections5585
No. of parameters367
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)1.18, 0.72

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.891.872.748 (8)166.6
N1—H1B···O5ii0.892.042.857 (8)152.5
N1—H1C···O60.891.862.734 (8)166.4
N2—H2A···O9iii0.891.972.801 (9)154.3
N2—H2B···O2iii0.891.932.795 (9)162.5
N2—H2B···O3iii0.892.573.000 (9)110.2
N2—H2C···O5iv0.891.902.747 (9)159.0
O9—H9···O1v0.821.892.695 (8)168.2
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+2, y+1, z+1; (iii) x+1, y1/2, z+1/2; (iv) x+1, y+1, z+1; (v) x1, y, z.
 

Acknowledgements

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

References

First citationBrandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (1997). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLiang, Z.-P., Li, J. & Huang, B.-Y. (2006). Acta Cryst. E62, o4761–o4762.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationLiang, Z.-P., Li, J., Hua, Y. & Wang, H.-L. (2007). Acta Cryst. E63, o3065.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationPolitzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–11.  Web of Science CrossRef PubMed CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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