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The title compound, 2C9H8NO2+·C4O42−, contains a dianion with approximately D4h symmetry [C—C = 1.465 (4)–1.470 (4) Å and C—O = 1.248 (4)–1.264 (4) Å]. Individual dianions are linked to four neighbouring 8-hydroxy­quinolinium cations by O...H—N [2.666 (4) and 2.681 (4) Å] and O...H—O [2.596 (3) and 2.605 (3) Å] hydrogen bonds to generate a polymeric chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805012523/bt6652sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805012523/bt6652Isup2.hkl
Contains datablock I

CCDC reference: 271826

Key indicators

  • Single-crystal X-ray study
  • T = 566 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.060
  • wR factor = 0.152
  • Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.26 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. O3' -C3' -O3' 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 0.00 Deg. O3' -O3' -C3' 1.555 1.555 1.555
Alert level G HYDTR01_ALERT_1_G Extra text has been found in the _refine_ls_hydrogen_treatment fie Explanatory text should be in the _publ_section_refinement field. Hydrogen treatment given as constr. Hydrogen treatment identified as constr
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: Siemens R3m/V User's Guide (Siemens, 1989); cell refinement: Siemens R3m/V User's Guide; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1995); software used to prepare material for publication: SHELXL97.

Bis(8-hydroxyquinolinium) squarate top
Crystal data top
2C9H8NO+·C4O42F(000) = 840
Mr = 404.37Dx = 1.502 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 15 reflections
a = 9.578 (3) Åθ = 7.5–15°
b = 7.3024 (17) ŵ = 0.11 mm1
c = 25.656 (5) ÅT = 566 K
β = 94.830 (13)°Prism, yellow
V = 1788.1 (6) Å30.42 × 0.36 × 0.28 mm
Z = 4
Data collection top
Siemens P4 four-circle
diffractometer
1640 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 25.0°, θmin = 2.1°
Profile–fitted scansh = 111
Absorption correction: psi-scan
(XPREP in SHELXTL-Plus; Sheldrick, 1995)
k = 18
Tmin = 0.930, Tmax = 0.973l = 3030
4380 measured reflections3 standard reflections every 100 reflections
3152 independent reflections intensity decay: 2%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.060Constrained.
wR(F2) = 0.152 w = 1/[σ2(Fo2) + (0.0609P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
3152 reflectionsΔρmax = 0.23 e Å3
272 parametersΔρmin = 0.21 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0063 (13)
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
N10.6813 (3)0.8221 (4)0.14085 (10)0.0388 (8)
H10.61660.85370.11730.047*
C20.6607 (4)0.8465 (5)0.19036 (13)0.0479 (10)
H20.57700.89810.19910.057*
C30.7618 (4)0.7966 (6)0.22986 (13)0.0486 (10)
H30.74570.81510.26470.058*
C40.8843 (4)0.7206 (5)0.21728 (14)0.0458 (10)
H40.95250.68750.24350.055*
C51.0310 (4)0.6133 (5)0.14795 (14)0.0463 (10)
H51.10080.57420.17280.056*
C61.0485 (4)0.5941 (5)0.09651 (14)0.0493 (10)
H61.13070.54250.08630.059*
C70.9437 (4)0.6515 (5)0.05810 (14)0.0455 (10)
H70.95830.63770.02290.055*
C80.8203 (3)0.7273 (5)0.07148 (13)0.0342 (9)
O80.7147 (2)0.7835 (4)0.03719 (9)0.0464 (7)
H80.74370.79630.00820.060*
C90.8024 (4)0.7480 (5)0.12567 (13)0.0320 (8)
C100.9077 (4)0.6921 (5)0.16403 (13)0.0375 (9)
N110.1840 (3)0.7290 (4)0.39237 (10)0.0367 (8)
H110.11920.70700.36790.044*
C120.1606 (4)0.6914 (5)0.44123 (13)0.0443 (10)
H120.07400.64430.44840.053*
C130.2623 (4)0.7207 (6)0.48181 (14)0.0495 (11)
H130.24460.69310.51600.059*
C140.3882 (4)0.7902 (5)0.47132 (13)0.0441 (10)
H140.45810.80610.49840.053*
C150.5403 (3)0.9195 (5)0.40691 (14)0.0463 (10)
H150.61100.94490.43300.056*
C160.5583 (4)0.9605 (6)0.35596 (14)0.0516 (11)
H160.64071.01700.34770.062*
C170.4544 (4)0.9188 (5)0.31586 (14)0.0467 (10)
H170.47040.94510.28140.056*
C180.3299 (4)0.8402 (5)0.32634 (12)0.0368 (9)
O180.2241 (2)0.7962 (4)0.29006 (9)0.0466 (7)
H180.24550.82590.26090.056*
C190.3086 (3)0.8020 (5)0.37935 (12)0.0309 (8)
C200.4141 (3)0.8385 (5)0.41982 (13)0.0370 (9)
C1'0.2130 (3)1.0903 (5)0.09176 (12)0.0361 (9)
O1'0.1701 (2)1.1717 (4)0.04998 (8)0.0500 (7)
C2'0.3375 (3)0.9830 (5)0.10938 (12)0.0368 (9)
O2'0.4466 (2)0.9394 (4)0.08811 (8)0.0497 (7)
C3'0.2803 (3)0.9535 (5)0.15989 (12)0.0381 (9)
O3'0.3223 (2)0.8681 (4)0.20064 (8)0.0522 (8)
C4'0.1560 (3)1.0622 (5)0.14257 (12)0.0353 (8)
O4'0.0474 (2)1.1076 (4)0.16304 (8)0.0473 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0371 (18)0.050 (2)0.0287 (16)0.0048 (16)0.0014 (13)0.0056 (14)
C20.046 (2)0.063 (3)0.036 (2)0.011 (2)0.0102 (17)0.002 (2)
C30.056 (3)0.067 (3)0.0231 (19)0.002 (2)0.0012 (18)0.0030 (19)
C40.044 (2)0.058 (3)0.033 (2)0.000 (2)0.0091 (18)0.0041 (19)
C50.036 (2)0.058 (3)0.044 (2)0.006 (2)0.0020 (17)0.005 (2)
C60.040 (2)0.058 (3)0.051 (2)0.009 (2)0.0081 (18)0.003 (2)
C70.048 (2)0.053 (3)0.037 (2)0.008 (2)0.0075 (17)0.0011 (19)
C80.032 (2)0.039 (2)0.0306 (18)0.0024 (17)0.0002 (16)0.0056 (16)
O80.0386 (15)0.0716 (19)0.0288 (13)0.0089 (14)0.0018 (11)0.0081 (12)
C90.034 (2)0.031 (2)0.031 (2)0.0030 (16)0.0026 (16)0.0041 (15)
C100.036 (2)0.041 (2)0.036 (2)0.0058 (18)0.0002 (16)0.0019 (17)
N110.0314 (17)0.0460 (19)0.0320 (17)0.0038 (15)0.0013 (13)0.0009 (14)
C120.042 (2)0.053 (3)0.038 (2)0.003 (2)0.0097 (18)0.0043 (19)
C130.052 (3)0.065 (3)0.032 (2)0.005 (2)0.0049 (19)0.0086 (19)
C140.046 (2)0.056 (3)0.0289 (19)0.004 (2)0.0087 (17)0.0043 (18)
C150.034 (2)0.059 (3)0.045 (2)0.006 (2)0.0040 (17)0.007 (2)
C160.037 (2)0.061 (3)0.058 (2)0.010 (2)0.0090 (18)0.006 (2)
C170.041 (2)0.063 (3)0.037 (2)0.008 (2)0.0094 (17)0.004 (2)
C180.036 (2)0.042 (2)0.0320 (18)0.0036 (18)0.0003 (16)0.0003 (17)
O180.0441 (15)0.0679 (18)0.0274 (13)0.0089 (14)0.0007 (11)0.0027 (12)
C190.0316 (19)0.033 (2)0.0284 (18)0.0035 (17)0.0038 (15)0.0008 (15)
C200.034 (2)0.041 (2)0.0360 (19)0.0033 (17)0.0008 (16)0.0032 (17)
C1'0.037 (2)0.048 (2)0.0221 (16)0.0025 (18)0.0052 (15)0.0011 (16)
O1'0.0416 (15)0.075 (2)0.0331 (14)0.0147 (14)0.0037 (11)0.0114 (14)
C2'0.038 (2)0.047 (2)0.0252 (17)0.0027 (19)0.0039 (15)0.0019 (16)
O2'0.0445 (15)0.0720 (19)0.0331 (13)0.0185 (15)0.0064 (11)0.0079 (13)
C3'0.0348 (19)0.048 (2)0.0305 (18)0.0010 (19)0.0002 (15)0.0029 (17)
O3'0.0462 (16)0.081 (2)0.0297 (13)0.0129 (15)0.0019 (11)0.0147 (14)
C4'0.0344 (19)0.044 (2)0.0267 (17)0.0020 (18)0.0000 (15)0.0027 (16)
O4'0.0405 (14)0.0704 (19)0.0318 (13)0.0163 (14)0.0085 (11)0.0024 (13)
Geometric parameters (Å, º) top
N1—C21.314 (4)C13—C141.356 (5)
N1—C91.366 (4)C13—H130.9300
N1—H10.8600C14—C201.410 (5)
C2—C31.390 (5)C14—H140.9300
C2—H20.9300C15—C161.366 (5)
C3—C41.361 (5)C15—C201.409 (5)
C3—H30.9300C15—H150.9300
C4—C101.418 (5)C16—C171.403 (5)
C4—H40.9300C16—H160.9300
C5—C61.352 (5)C17—C181.370 (5)
C5—C101.406 (5)C17—H170.9300
C5—H50.9300C18—O181.355 (4)
C6—C71.410 (5)C18—C191.420 (4)
C6—H60.9300O18—H180.8200
C7—C81.375 (5)C19—C201.412 (4)
C7—H70.9300C1'—O1'1.264 (4)
C8—O81.347 (4)C1'—C2'1.465 (5)
C8—C91.423 (4)C1'—C4'1.470 (4)
O8—H80.8200C2'—O2'1.260 (4)
C9—C101.409 (4)C2'—C3'1.465 (4)
N11—C121.321 (4)C3'—O3'1.254 (4)
N11—C191.373 (4)C3'—O3'1.254 (4)
N11—H110.8600C3'—C4'1.468 (4)
C12—C131.381 (5)C4'—O4'1.248 (4)
C12—H120.9300
C2—N1—C9122.0 (3)C12—C13—H13120.3
C2—N1—H1119.0C13—C14—C20120.6 (3)
C9—N1—H1119.0C13—C14—H14119.7
N1—C2—C3121.1 (3)C20—C14—H14119.7
N1—C2—H2119.4C16—C15—C20119.8 (3)
C3—C2—H2119.4C16—C15—H15120.1
C4—C3—C2119.7 (3)C20—C15—H15120.1
C4—C3—H3120.2C15—C16—C17121.0 (3)
C2—C3—H3120.2C15—C16—H16119.5
C3—C4—C10119.9 (3)C17—C16—H16119.5
C3—C4—H4120.1C18—C17—C16121.5 (3)
C10—C4—H4120.1C18—C17—H17119.2
C6—C5—C10120.4 (3)C16—C17—H17119.2
C6—C5—H5119.8O18—C18—C17125.2 (3)
C10—C5—H5119.8O18—C18—C19116.9 (3)
C5—C6—C7120.8 (3)C17—C18—C19117.9 (3)
C5—C6—H6119.6C18—O18—H18109.5
C7—C6—H6119.6N11—C19—C20118.5 (3)
C8—C7—C6121.5 (3)N11—C19—C18120.5 (3)
C8—C7—H7119.3C20—C19—C18121.0 (3)
C6—C7—H7119.3C15—C20—C14123.2 (3)
O8—C8—C7125.0 (3)C15—C20—C19118.8 (3)
O8—C8—C9117.4 (3)C14—C20—C19118.1 (3)
C7—C8—C9117.6 (3)O1'—C1'—C2'135.3 (3)
C8—O8—H8109.5O1'—C1'—C4'134.4 (3)
N1—C9—C10119.4 (3)C2'—C1'—C4'90.3 (2)
N1—C9—C8119.7 (3)O2'—C2'—C3'137.0 (3)
C10—C9—C8120.9 (3)O2'—C2'—C1'133.2 (3)
C5—C10—C9118.9 (3)C3'—C2'—C1'89.8 (3)
C5—C10—C4123.2 (3)O3'—C3'—O3'0.0 (2)
C9—C10—C4117.9 (3)O3'—C3'—C2'133.9 (3)
C12—N11—C19122.1 (3)O3'—C3'—C2'133.9 (3)
C12—N11—H11118.9O3'—C3'—C4'135.7 (3)
C19—N11—H11118.9O3'—C3'—C4'135.7 (3)
N11—C12—C13121.2 (3)C2'—C3'—C4'90.4 (3)
N11—C12—H12119.4O3'—O3'—C3'0 (10)
C13—C12—H12119.4O4'—C4'—C3'134.4 (3)
C14—C13—C12119.4 (3)O4'—C4'—C1'136.1 (3)
C14—C13—H13120.3C3'—C4'—C1'89.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O1i0.932.563.168 (4)123
O8—H8···O1i0.821.782.596 (3)172
N1—H1···O20.861.842.666 (4)159
C17—H17···O30.932.483.138 (4)128
O18—H18···O30.821.792.605 (3)169
N11—H11···O4ii0.861.872.681 (4)157
Symmetry codes: (i) x+1, y+2, z; (ii) x, y1/2, z+1/2.
 

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