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In the crystal of the title compound, 2C9H8NO+·C4H2Br2O42−·2C4H4Br2O4, the di­bromo­succinate dianion and di­bromo­succinic acid mol­ecules each lie on an inversion center. They interact via hydrogen bonding. The hydroxy­quinolinium cations are hydrogen bonded to both the dibromosuccinate anion and di­bromo­succinic acid mol­ecules. The overlapped arrangement and short face-to-face distance of 3.431 (17) Å indicate the existence of π–π stacking between hydroxy­quinolinium rings in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001704/hb6142sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001704/hb6142Isup2.hkl
Contains datablock I

CCDC reference: 264062

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.014 Å
  • R factor = 0.064
  • wR factor = 0.170
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Br3 - C16 .. 16.53 su PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C16
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT213_ALERT_2_C Atom C16 has ADP max/min Ratio ............. 3.20 prolat PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C15 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 14 PLAT360_ALERT_2_C Short C(sp3)-C(sp3) Bond C16 - C16_c ... 1.37 Ang.
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR2 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

8-Hydroxyquinolinium hemi(dibromosuccinate) dibromosuccinic acid top
Crystal data top
2C9H8NO+·C4H2Br2O42·2C4H4Br2O4Z = 1
Mr = 1117.98F(000) = 542
Triclinic, P1Dx = 2.065 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9687 (8) ÅCell parameters from 4238 reflections
b = 11.4468 (12) Åθ = 2.0–24.5°
c = 12.6870 (13) ŵ = 6.77 mm1
α = 110.396 (2)°T = 295 K
β = 100.042 (2)°Prism, yellow
γ = 100.915 (2)°0.26 × 0.20 × 0.18 mm
V = 899.10 (17) Å3
Data collection top
Rigaku R-AXIS RAPID
diffractometer
3147 independent reflections
Radiation source: fine-focus sealed tube2360 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 10.00 pixels mm-1θmax = 25.1°, θmin = 1.8°
ω scansh = 87
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1313
Tmin = 0.170, Tmax = 0.292l = 1115
4687 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)] = 0.064Hydrogen site location: difmap (O-H and N-H) and geom (C-H)
wR(F2) = 0.170H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0697P)2 + 5.0115P]
where P = (Fo2 + 2Fc2)/3
3147 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.91 e Å3
0 restraintsΔρmin = 0.96 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.

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
Br10.82192 (13)0.58880 (9)0.62382 (8)0.0416 (3)
Br20.68209 (14)0.14188 (10)0.07866 (10)0.0525 (3)
Br30.69861 (16)0.51918 (12)0.08931 (10)0.0586 (4)
N10.6903 (10)0.0796 (6)0.3695 (6)0.0324 (15)
O10.8055 (11)0.2484 (6)0.5924 (6)0.0540 (17)
O110.6640 (9)0.3102 (6)0.3460 (5)0.0404 (14)
O120.6717 (9)0.5056 (6)0.3439 (5)0.0384 (14)
O130.8228 (12)0.1533 (7)0.0592 (6)0.0568 (19)
O140.8386 (10)0.2001 (6)0.1283 (5)0.0474 (16)
O150.7810 (10)0.4240 (5)0.1556 (5)0.0395 (14)
O160.9551 (11)0.6253 (6)0.1971 (5)0.0488 (16)
C20.6360 (13)0.0002 (9)0.2567 (8)0.040 (2)
H20.61100.03370.20020.048*
C30.6165 (15)0.1308 (10)0.2233 (8)0.051 (2)
H30.57550.18590.14480.061*
C40.6581 (13)0.1783 (9)0.3070 (8)0.042 (2)
H40.64860.26610.28500.050*
C50.7571 (13)0.1406 (8)0.5157 (8)0.041 (2)
H50.75060.22750.49780.049*
C60.8068 (13)0.0580 (9)0.6280 (8)0.042 (2)
H60.83110.08890.68640.050*
C70.8227 (12)0.0770 (9)0.6587 (8)0.042 (2)
H70.85710.13310.73670.050*
C80.7874 (12)0.1238 (8)0.5734 (7)0.0349 (19)
C90.7293 (11)0.0357 (7)0.4559 (7)0.0282 (17)
C100.7142 (11)0.0981 (8)0.4238 (7)0.0310 (18)
C110.6438 (12)0.4194 (8)0.3889 (7)0.0287 (17)
C120.5832 (11)0.4658 (8)0.5027 (7)0.0297 (17)
H120.53780.39190.52290.036*
C130.8557 (13)0.1305 (8)0.0270 (8)0.0358 (19)
C140.9144 (14)0.0087 (9)0.0245 (8)0.044 (2)
H140.94430.00990.10330.052*
C150.8866 (14)0.5106 (9)0.1317 (8)0.040 (2)
C160.920 (2)0.4655 (10)0.0112 (10)0.086 (5)
H160.90550.37220.02190.104*
H10.70070.16290.38810.050*
H1A0.91100.30990.65870.050*
H12A0.70800.47500.27400.050*
H14A0.79500.27300.13100.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0300 (5)0.0535 (6)0.0352 (5)0.0122 (4)0.0038 (4)0.0121 (4)
Br20.0354 (5)0.0420 (6)0.0705 (7)0.0088 (4)0.0063 (5)0.0153 (5)
Br30.0442 (6)0.0808 (8)0.0567 (7)0.0286 (6)0.0088 (5)0.0301 (6)
N10.027 (3)0.034 (4)0.041 (4)0.014 (3)0.010 (3)0.017 (3)
O10.065 (5)0.030 (3)0.050 (4)0.012 (3)0.005 (3)0.003 (3)
O110.052 (4)0.038 (3)0.038 (3)0.022 (3)0.024 (3)0.013 (3)
O120.052 (4)0.042 (3)0.039 (3)0.027 (3)0.034 (3)0.020 (3)
O130.085 (5)0.054 (4)0.041 (4)0.039 (4)0.019 (4)0.018 (3)
O140.059 (4)0.047 (4)0.040 (4)0.024 (3)0.025 (3)0.010 (3)
O150.058 (4)0.031 (3)0.036 (3)0.011 (3)0.031 (3)0.012 (3)
O160.068 (5)0.033 (4)0.036 (3)0.009 (3)0.024 (3)0.000 (3)
C20.039 (5)0.053 (6)0.036 (5)0.021 (4)0.010 (4)0.024 (5)
C30.055 (6)0.052 (6)0.034 (5)0.021 (5)0.005 (4)0.002 (5)
C40.036 (5)0.039 (5)0.044 (5)0.016 (4)0.007 (4)0.006 (4)
C50.037 (5)0.033 (5)0.056 (6)0.013 (4)0.012 (4)0.021 (5)
C60.037 (5)0.046 (5)0.046 (6)0.004 (4)0.008 (4)0.029 (5)
C70.026 (4)0.061 (6)0.037 (5)0.015 (4)0.011 (4)0.017 (5)
C80.031 (4)0.036 (5)0.039 (5)0.012 (4)0.015 (4)0.012 (4)
C90.022 (4)0.029 (4)0.035 (4)0.010 (3)0.008 (3)0.013 (4)
C100.019 (4)0.038 (5)0.035 (5)0.008 (3)0.007 (3)0.013 (4)
C110.034 (4)0.032 (4)0.025 (4)0.016 (4)0.012 (3)0.013 (4)
C120.029 (4)0.031 (4)0.033 (4)0.010 (3)0.011 (3)0.014 (4)
C130.038 (5)0.040 (5)0.035 (5)0.023 (4)0.015 (4)0.011 (4)
C140.052 (6)0.046 (5)0.040 (5)0.021 (5)0.023 (4)0.017 (4)
C150.052 (6)0.036 (5)0.038 (5)0.020 (4)0.024 (4)0.011 (4)
C160.157 (13)0.038 (6)0.065 (8)0.000 (7)0.082 (9)0.011 (5)
Geometric parameters (Å, º) top
Br1—C121.955 (8)C4—C101.381 (12)
Br2—C141.984 (10)C4—H40.9300
Br3—C162.144 (17)C5—C61.345 (13)
N1—C21.339 (11)C5—C101.419 (12)
N1—C91.364 (10)C5—H50.9300
N1—H10.884C6—C71.433 (13)
O1—C81.338 (10)C6—H60.9300
O1—H1A0.959C7—C81.371 (12)
O11—C111.223 (9)C7—H70.9300
O12—C111.303 (9)C8—C91.411 (12)
O12—H12A0.932C9—C101.418 (11)
O13—C131.204 (10)C11—C121.519 (11)
O14—C131.295 (10)C12—C12i1.522 (15)
O14—H14A0.932C12—H120.9800
O15—C151.276 (10)C13—C141.516 (12)
O16—C151.226 (10)C14—C14ii1.454 (17)
C2—C31.381 (13)C14—H140.9800
C2—H20.9300C15—C161.509 (13)
C3—C41.365 (13)C16—C16iii1.38 (2)
C3—H30.9300C16—H160.9800
C2—N1—C9122.0 (7)C4—C10—C9118.8 (8)
C2—N1—H1118.6C4—C10—C5124.2 (8)
C9—N1—H1119.4C9—C10—C5117.0 (7)
C8—O1—H1A115.8O11—C11—O12124.6 (7)
C11—O12—H12A112.5O11—C11—C12121.5 (7)
C13—O14—H14A114.3O12—C11—C12114.0 (6)
N1—C2—C3120.8 (8)C11—C12—C12i112.7 (8)
N1—C2—H2119.6C11—C12—Br1107.8 (5)
C3—C2—H2119.6C12i—C12—Br1108.1 (7)
C4—C3—C2119.1 (9)C11—C12—H12109.4
C4—C3—H3120.5C12i—C12—H12109.4
C2—C3—H3120.5Br1—C12—H12109.4
C3—C4—C10121.0 (8)O13—C13—O14125.9 (8)
C3—C4—H4119.5O13—C13—C14121.6 (8)
C10—C4—H4119.5O14—C13—C14112.5 (8)
C6—C5—C10121.4 (8)C14ii—C14—C13113.0 (10)
C6—C5—H5119.3C14ii—C14—Br2106.4 (8)
C10—C5—H5119.3C13—C14—Br2107.7 (6)
C5—C6—C7120.8 (8)C14ii—C14—H14109.9
C5—C6—H6119.6C13—C14—H14109.9
C7—C6—H6119.6Br2—C14—H14109.9
C8—C7—C6120.1 (8)O16—C15—O15125.1 (8)
C8—C7—H7119.9O16—C15—C16119.3 (8)
C6—C7—H7119.9O15—C15—C16115.6 (8)
O1—C8—C7125.0 (8)C16iii—C16—C15120.1 (14)
O1—C8—C9116.4 (7)C16iii—C16—Br393.8 (13)
C7—C8—C9118.6 (8)C15—C16—Br3105.0 (8)
N1—C9—C8119.6 (7)C16iii—C16—H16112.0
N1—C9—C10118.3 (7)C15—C16—H16112.0
C8—C9—C10122.0 (7)Br3—C16—H16112.0
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+2, y, z; (iii) x+2, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O110.881.982.793 (10)152
O1—H1A···O16iv0.961.722.617 (9)154
O12—H12A···O150.931.622.551 (9)178
O14—H14A···O150.931.672.582 (10)165
Symmetry code: (iv) x+2, y+1, z+1.
 

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