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All atoms of the title compound, C6H6Br2N+·Br, except for two H atoms of the NH3+ group, lie in a crystallographic mirror plane. The packing within the plane is determined by hydrogen bonds N+—H...Br and C—H...Br, and by Br...Br contacts. Planes are linked by hydrogen bonds N+—H...Br. The packing is completely different from that of the previously known form [López–Duplá, Jones & Vancea (2003). Z. Naturforsch. Teil B, 58, 191–200].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301465X/bt6297sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680301465X/bt6297Isup2.hkl
Contains datablock I

CCDC reference: 221669

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.030
  • wR factor = 0.074
  • Data-to-parameter ratio = 20.7

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.904 Tmax scaled 0.447 Tmin scaled 0.211

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.

2,5-dibromoanilinium bromide top
Crystal data top
C6H6Br2N+·BrF(000) = 308
Mr = 331.85Dx = 2.460 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
a = 8.3640 (12) ÅCell parameters from 3592 reflections
b = 6.5476 (11) Åθ = 2.5–30.5°
c = 8.5472 (12) ŵ = 13.43 mm1
β = 106.815 (5)°T = 133 K
V = 448.07 (12) Å3Prism, colourless
Z = 20.16 × 0.09 × 0.06 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
1408 independent reflections
Radiation source: fine-focus sealed tube1200 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.041
Detector resolution: 8.192 pixels mm-1θmax = 30.0°, θmin = 2.5°
ω and φ scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 1998)
k = 99
Tmin = 0.233, Tmax = 0.494l = 1212
7449 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)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0487P)2]
where P = (Fo2 + 2Fc2)/3
1408 reflections(Δ/σ)max < 0.001
68 parametersΔρmax = 0.88 e Å3
1 restraintΔρmin = 1.27 e Å3
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.

Contacts:

3.3379 (0.0006) Br1 - Br3_$3 3.6977 (0.0006) Br2 - Br3_$4

173.42 (0.11) C2 - Br1 - Br3_$3 176.47 (0.10) C5 - Br2 - Br3_$4

$3 x + 1, y, z $4 x, y, z + 1

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
Br11.07907 (4)0.25000.21456 (4)0.02239 (12)
Br20.56532 (5)0.25000.66742 (5)0.02522 (12)
N0.6968 (4)0.25000.0977 (4)0.0191 (6)
H010.581 (3)0.25000.063 (5)0.031 (12)*
H020.728 (3)0.137 (4)0.051 (3)0.023 (7)*
C10.7619 (4)0.25000.2757 (4)0.0185 (7)
C20.9341 (4)0.25000.3492 (4)0.0183 (6)
C30.9960 (5)0.25000.5177 (4)0.0214 (7)
H31.11330.25000.56780.026*
C40.8878 (5)0.25000.6142 (4)0.0215 (7)
H40.92990.25000.73000.026*
C50.7166 (4)0.25000.5378 (4)0.0180 (7)
C60.6497 (4)0.25000.3687 (4)0.0186 (7)
H60.53250.25000.31860.022*
Br30.29461 (4)0.25000.05871 (4)0.01974 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.01748 (19)0.0247 (2)0.0264 (2)0.0000.00854 (14)0.000
Br20.0254 (2)0.0306 (2)0.0221 (2)0.0000.01067 (14)0.000
N0.0181 (14)0.0202 (15)0.0185 (13)0.0000.0046 (11)0.000
C10.0192 (16)0.0145 (16)0.0208 (16)0.0000.0041 (13)0.000
C20.0172 (16)0.0153 (16)0.0221 (16)0.0000.0054 (12)0.000
C30.0172 (16)0.0197 (17)0.0241 (17)0.0000.0011 (13)0.000
C40.0271 (18)0.0172 (17)0.0180 (16)0.0000.0031 (13)0.000
C50.0177 (16)0.0182 (16)0.0193 (16)0.0000.0071 (13)0.000
C60.0183 (16)0.0165 (16)0.0201 (16)0.0000.0041 (13)0.000
Br30.01522 (17)0.02049 (19)0.02266 (18)0.0000.00412 (13)0.000
Geometric parameters (Å, º) top
Br1—C21.898 (4)C4—C51.391 (5)
Br2—C51.908 (3)C5—C61.391 (5)
N—C11.460 (4)N—H010.93 (3)
C1—C61.394 (5)N—H020.92 (2)
C1—C21.394 (5)C3—H30.9500
C2—C31.382 (5)C4—H40.9500
C3—C41.390 (5)C6—H60.9500
C6—C1—C2121.4 (3)C5—C6—C1117.3 (3)
C6—C1—N119.0 (3)C1—N—H01112 (3)
C2—C1—N119.7 (3)C1—N—H02112.8 (17)
C3—C2—C1119.8 (3)H01—N—H02105 (2)
C3—C2—Br1121.3 (3)C2—C3—H3119.8
C1—C2—Br1119.0 (3)C4—C3—H3119.8
C2—C3—C4120.4 (3)C3—C4—H4120.7
C3—C4—C5118.7 (3)C5—C4—H4120.7
C6—C5—C4122.5 (3)C5—C6—H6121.4
C6—C5—Br2118.0 (3)C1—C6—H6121.4
C4—C5—Br2119.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H01···Br30.93 (3)2.32 (3)3.240 (3)173 (4)
N—H02···Br3i0.92 (2)2.54 (3)3.2936 (6)139 (2)
C3—H3···Br3ii0.953.113.757 (4)127
C4—H4···Br3ii0.953.063.727 (4)128
Symmetry codes: (i) x+1, y, z; (ii) x+1, y, z+1.
 

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