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
CCDC reference: 264062
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (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
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−·2C4H4Br2O4 | Z = 1 |
Mr = 1117.98 | F(000) = 542 |
Triclinic, P1 | Dx = 2.065 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9687 (8) Å | Cell parameters from 4238 reflections |
b = 11.4468 (12) Å | θ = 2.0–24.5° |
c = 12.6870 (13) Å | µ = 6.77 mm−1 |
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 tube | 2360 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
Detector resolution: 10.00 pixels mm-1 | θmax = 25.1°, θmin = 1.8° |
ω scans | h = −8→7 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −13→13 |
Tmin = 0.170, Tmax = 0.292 | l = −11→15 |
4687 measured reflections | |
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)] = 0.064 | Hydrogen site location: difmap (O-H and N-H) and geom (C-H) |
wR(F2) = 0.170 | H-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 parameters | Δρmax = 0.91 e Å−3 |
0 restraints | Δρmin = −0.96 e Å−3 |
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 | Uiso*/Ueq | |
Br1 | 0.82192 (13) | 0.58880 (9) | 0.62382 (8) | 0.0416 (3) | |
Br2 | 0.68209 (14) | −0.14188 (10) | −0.07866 (10) | 0.0525 (3) | |
Br3 | 0.69861 (16) | 0.51918 (12) | −0.08931 (10) | 0.0586 (4) | |
N1 | 0.6903 (10) | 0.0796 (6) | 0.3695 (6) | 0.0324 (15) | |
O1 | 0.8055 (11) | 0.2484 (6) | 0.5924 (6) | 0.0540 (17) | |
O11 | 0.6640 (9) | 0.3102 (6) | 0.3460 (5) | 0.0404 (14) | |
O12 | 0.6717 (9) | 0.5056 (6) | 0.3439 (5) | 0.0384 (14) | |
O13 | 0.8228 (12) | 0.1533 (7) | −0.0592 (6) | 0.0568 (19) | |
O14 | 0.8386 (10) | 0.2001 (6) | 0.1283 (5) | 0.0474 (16) | |
O15 | 0.7810 (10) | 0.4240 (5) | 0.1556 (5) | 0.0395 (14) | |
O16 | 0.9551 (11) | 0.6253 (6) | 0.1971 (5) | 0.0488 (16) | |
C2 | 0.6360 (13) | 0.0002 (9) | 0.2567 (8) | 0.040 (2) | |
H2 | 0.6110 | 0.0337 | 0.2002 | 0.048* | |
C3 | 0.6165 (15) | −0.1308 (10) | 0.2233 (8) | 0.051 (2) | |
H3 | 0.5755 | −0.1859 | 0.1448 | 0.061* | |
C4 | 0.6581 (13) | −0.1783 (9) | 0.3070 (8) | 0.042 (2) | |
H4 | 0.6486 | −0.2661 | 0.2850 | 0.050* | |
C5 | 0.7571 (13) | −0.1406 (8) | 0.5157 (8) | 0.041 (2) | |
H5 | 0.7506 | −0.2275 | 0.4978 | 0.049* | |
C6 | 0.8068 (13) | −0.0580 (9) | 0.6280 (8) | 0.042 (2) | |
H6 | 0.8311 | −0.0889 | 0.6864 | 0.050* | |
C7 | 0.8227 (12) | 0.0770 (9) | 0.6587 (8) | 0.042 (2) | |
H7 | 0.8571 | 0.1331 | 0.7367 | 0.050* | |
C8 | 0.7874 (12) | 0.1238 (8) | 0.5734 (7) | 0.0349 (19) | |
C9 | 0.7293 (11) | 0.0357 (7) | 0.4559 (7) | 0.0282 (17) | |
C10 | 0.7142 (11) | −0.0981 (8) | 0.4238 (7) | 0.0310 (18) | |
C11 | 0.6438 (12) | 0.4194 (8) | 0.3889 (7) | 0.0287 (17) | |
C12 | 0.5832 (11) | 0.4658 (8) | 0.5027 (7) | 0.0297 (17) | |
H12 | 0.5378 | 0.3919 | 0.5229 | 0.036* | |
C13 | 0.8557 (13) | 0.1305 (8) | 0.0270 (8) | 0.0358 (19) | |
C14 | 0.9144 (14) | 0.0087 (9) | 0.0245 (8) | 0.044 (2) | |
H14 | 0.9443 | 0.0099 | 0.1033 | 0.052* | |
C15 | 0.8866 (14) | 0.5106 (9) | 0.1317 (8) | 0.040 (2) | |
C16 | 0.920 (2) | 0.4655 (10) | 0.0112 (10) | 0.086 (5) | |
H16 | 0.9055 | 0.3722 | −0.0219 | 0.104* | |
H1 | 0.7007 | 0.1629 | 0.3881 | 0.050* | |
H1A | 0.9110 | 0.3099 | 0.6587 | 0.050* | |
H12A | 0.7080 | 0.4750 | 0.2740 | 0.050* | |
H14A | 0.7950 | 0.2730 | 0.1310 | 0.050* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Br1 | 0.0300 (5) | 0.0535 (6) | 0.0352 (5) | 0.0122 (4) | 0.0038 (4) | 0.0121 (4) |
Br2 | 0.0354 (5) | 0.0420 (6) | 0.0705 (7) | 0.0088 (4) | 0.0063 (5) | 0.0153 (5) |
Br3 | 0.0442 (6) | 0.0808 (8) | 0.0567 (7) | 0.0286 (6) | 0.0088 (5) | 0.0301 (6) |
N1 | 0.027 (3) | 0.034 (4) | 0.041 (4) | 0.014 (3) | 0.010 (3) | 0.017 (3) |
O1 | 0.065 (5) | 0.030 (3) | 0.050 (4) | 0.012 (3) | 0.005 (3) | 0.003 (3) |
O11 | 0.052 (4) | 0.038 (3) | 0.038 (3) | 0.022 (3) | 0.024 (3) | 0.013 (3) |
O12 | 0.052 (4) | 0.042 (3) | 0.039 (3) | 0.027 (3) | 0.034 (3) | 0.020 (3) |
O13 | 0.085 (5) | 0.054 (4) | 0.041 (4) | 0.039 (4) | 0.019 (4) | 0.018 (3) |
O14 | 0.059 (4) | 0.047 (4) | 0.040 (4) | 0.024 (3) | 0.025 (3) | 0.010 (3) |
O15 | 0.058 (4) | 0.031 (3) | 0.036 (3) | 0.011 (3) | 0.031 (3) | 0.012 (3) |
O16 | 0.068 (5) | 0.033 (4) | 0.036 (3) | 0.009 (3) | 0.024 (3) | 0.000 (3) |
C2 | 0.039 (5) | 0.053 (6) | 0.036 (5) | 0.021 (4) | 0.010 (4) | 0.024 (5) |
C3 | 0.055 (6) | 0.052 (6) | 0.034 (5) | 0.021 (5) | 0.005 (4) | 0.002 (5) |
C4 | 0.036 (5) | 0.039 (5) | 0.044 (5) | 0.016 (4) | 0.007 (4) | 0.006 (4) |
C5 | 0.037 (5) | 0.033 (5) | 0.056 (6) | 0.013 (4) | 0.012 (4) | 0.021 (5) |
C6 | 0.037 (5) | 0.046 (5) | 0.046 (6) | 0.004 (4) | 0.008 (4) | 0.029 (5) |
C7 | 0.026 (4) | 0.061 (6) | 0.037 (5) | 0.015 (4) | 0.011 (4) | 0.017 (5) |
C8 | 0.031 (4) | 0.036 (5) | 0.039 (5) | 0.012 (4) | 0.015 (4) | 0.012 (4) |
C9 | 0.022 (4) | 0.029 (4) | 0.035 (4) | 0.010 (3) | 0.008 (3) | 0.013 (4) |
C10 | 0.019 (4) | 0.038 (5) | 0.035 (5) | 0.008 (3) | 0.007 (3) | 0.013 (4) |
C11 | 0.034 (4) | 0.032 (4) | 0.025 (4) | 0.016 (4) | 0.012 (3) | 0.013 (4) |
C12 | 0.029 (4) | 0.031 (4) | 0.033 (4) | 0.010 (3) | 0.011 (3) | 0.014 (4) |
C13 | 0.038 (5) | 0.040 (5) | 0.035 (5) | 0.023 (4) | 0.015 (4) | 0.011 (4) |
C14 | 0.052 (6) | 0.046 (5) | 0.040 (5) | 0.021 (5) | 0.023 (4) | 0.017 (4) |
C15 | 0.052 (6) | 0.036 (5) | 0.038 (5) | 0.020 (4) | 0.024 (4) | 0.011 (4) |
C16 | 0.157 (13) | 0.038 (6) | 0.065 (8) | 0.000 (7) | 0.082 (9) | 0.011 (5) |
Geometric parameters (Å, º) top
Br1—C12 | 1.955 (8) | C4—C10 | 1.381 (12) |
Br2—C14 | 1.984 (10) | C4—H4 | 0.9300 |
Br3—C16 | 2.144 (17) | C5—C6 | 1.345 (13) |
N1—C2 | 1.339 (11) | C5—C10 | 1.419 (12) |
N1—C9 | 1.364 (10) | C5—H5 | 0.9300 |
N1—H1 | 0.884 | C6—C7 | 1.433 (13) |
O1—C8 | 1.338 (10) | C6—H6 | 0.9300 |
O1—H1A | 0.959 | C7—C8 | 1.371 (12) |
O11—C11 | 1.223 (9) | C7—H7 | 0.9300 |
O12—C11 | 1.303 (9) | C8—C9 | 1.411 (12) |
O12—H12A | 0.932 | C9—C10 | 1.418 (11) |
O13—C13 | 1.204 (10) | C11—C12 | 1.519 (11) |
O14—C13 | 1.295 (10) | C12—C12i | 1.522 (15) |
O14—H14A | 0.932 | C12—H12 | 0.9800 |
O15—C15 | 1.276 (10) | C13—C14 | 1.516 (12) |
O16—C15 | 1.226 (10) | C14—C14ii | 1.454 (17) |
C2—C3 | 1.381 (13) | C14—H14 | 0.9800 |
C2—H2 | 0.9300 | C15—C16 | 1.509 (13) |
C3—C4 | 1.365 (13) | C16—C16iii | 1.38 (2) |
C3—H3 | 0.9300 | C16—H16 | 0.9800 |
| | | |
C2—N1—C9 | 122.0 (7) | C4—C10—C9 | 118.8 (8) |
C2—N1—H1 | 118.6 | C4—C10—C5 | 124.2 (8) |
C9—N1—H1 | 119.4 | C9—C10—C5 | 117.0 (7) |
C8—O1—H1A | 115.8 | O11—C11—O12 | 124.6 (7) |
C11—O12—H12A | 112.5 | O11—C11—C12 | 121.5 (7) |
C13—O14—H14A | 114.3 | O12—C11—C12 | 114.0 (6) |
N1—C2—C3 | 120.8 (8) | C11—C12—C12i | 112.7 (8) |
N1—C2—H2 | 119.6 | C11—C12—Br1 | 107.8 (5) |
C3—C2—H2 | 119.6 | C12i—C12—Br1 | 108.1 (7) |
C4—C3—C2 | 119.1 (9) | C11—C12—H12 | 109.4 |
C4—C3—H3 | 120.5 | C12i—C12—H12 | 109.4 |
C2—C3—H3 | 120.5 | Br1—C12—H12 | 109.4 |
C3—C4—C10 | 121.0 (8) | O13—C13—O14 | 125.9 (8) |
C3—C4—H4 | 119.5 | O13—C13—C14 | 121.6 (8) |
C10—C4—H4 | 119.5 | O14—C13—C14 | 112.5 (8) |
C6—C5—C10 | 121.4 (8) | C14ii—C14—C13 | 113.0 (10) |
C6—C5—H5 | 119.3 | C14ii—C14—Br2 | 106.4 (8) |
C10—C5—H5 | 119.3 | C13—C14—Br2 | 107.7 (6) |
C5—C6—C7 | 120.8 (8) | C14ii—C14—H14 | 109.9 |
C5—C6—H6 | 119.6 | C13—C14—H14 | 109.9 |
C7—C6—H6 | 119.6 | Br2—C14—H14 | 109.9 |
C8—C7—C6 | 120.1 (8) | O16—C15—O15 | 125.1 (8) |
C8—C7—H7 | 119.9 | O16—C15—C16 | 119.3 (8) |
C6—C7—H7 | 119.9 | O15—C15—C16 | 115.6 (8) |
O1—C8—C7 | 125.0 (8) | C16iii—C16—C15 | 120.1 (14) |
O1—C8—C9 | 116.4 (7) | C16iii—C16—Br3 | 93.8 (13) |
C7—C8—C9 | 118.6 (8) | C15—C16—Br3 | 105.0 (8) |
N1—C9—C8 | 119.6 (7) | C16iii—C16—H16 | 112.0 |
N1—C9—C10 | 118.3 (7) | C15—C16—H16 | 112.0 |
C8—C9—C10 | 122.0 (7) | Br3—C16—H16 | 112.0 |
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···A | D—H | H···A | D···A | D—H···A |
N1—H1···O11 | 0.88 | 1.98 | 2.793 (10) | 152 |
O1—H1A···O16iv | 0.96 | 1.72 | 2.617 (9) | 154 |
O12—H12A···O15 | 0.93 | 1.62 | 2.551 (9) | 178 |
O14—H14A···O15 | 0.93 | 1.67 | 2.582 (10) | 165 |
Symmetry code: (iv) −x+2, −y+1, −z+1. |