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Structural features of moderate-to-strong O—H
O hydrogen bonds are related to the frequencies of O—H stretching vibrations and to the electric polarizability distribution in the donor and acceptor functional groups for crystals synthesized from the 1,2,4,5-benzenetetracarboxylic (pyromellitic) acid, namely: bis(3-aminopyridinium) dihydrogen pyromellitate tetrahydrate, (1); bis(3-carboxypyridinium) dihydrogen pyromellitate, (2); bis(3-carboxyphenylammonium) dihydrogen pyromellitate dihydrate, (3); and bis(4-carboxyphenylammonium) dihydrogen pyromellitate, (4). A combination of single-crystal X-ray diffraction, powder Raman spectroscopy and first-principle calculations in both crystalline and gaseous phases has shown that changes in the O—H
O hydrogen-bond geometry can be followed by changes in the corresponding spectral modes. Vibrational properties of moderate hydrogen bonds can be estimated from correlations based on statistical analysis of several compounds [Novak (1974).
Struct. Bond. 18, 177–216]. However, frequencies related to very short O—H
O bonds can only be predicted by relationships built from a subset of structurally similar systems. Moreover, the way in which hydrogen bonds affect the polarizability of donor and acceptor groups depends on their strength. Moderate interactions enhance the polarizability and make it more anisotropic. Shorter hydrogen bonds may decrease the polarizability of a group as a consequence of the volume restraint implied by the neighbour molecule within a hydrogen-bonded aggregate. This is significant for evaluation of the electric susceptibility in crystals and, therefore, for estimation of refractive indices and birefringence.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620001067/px5021sup1.cif Contains datablocks global, comp1-120K, comp2-120K, comp3-120K, comp4-120K, comp1-293K, comp2-293K, comp3-293K, comp4-293K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp1-120Ksup2.hkl Contains datablock comp1_120K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp2-120Ksup3.hkl Contains datablock comp2-120K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp3-120Ksup4.hkl Contains datablock comp3-120K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp4-120Ksup5.hkl Contains datablock comp4-120K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp1-293Ksup6.hkl Contains datablock comp1-293K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp2-293Ksup7.hkl Contains datablock comp2-293K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp3-293Ksup8.hkl Contains datablock comp3-293K |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520620001067/px5021comp4-293Ksup9.hkl Contains datablock comp4-293K |
| Text file https://doi.org/10.1107/S2052520620001067/px5021sup10.txt B3LYP/6-31G(d,p) optimized crystal geometries for compounds 1-4. |
| Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620001067/px5021sup11.pdf Tables S1, S2, Fig. S1 and Sections S1-S4.8 |
CCDC references: 1960157; 1960158; 1960159; 1960160; 1960161; 1960162; 1960163; 1960164
For all structures, data collection: CrysAlis PRO (Rigaku Oxford Diffraction, 2018); cell refinement: CrysAlis PRO (Rigaku Oxford Diffraction, 2018); data reduction: CrysAlis PRO (Rigaku Oxford Diffraction, 2018); program(s) used to solve structure: SHELXS86 (Sheldrick, 1986); 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 publication routines (Farrugia, 1999).
bis(3-Aminopyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate tetrahydrate (comp1-120K)
top
Crystal data top
C10H4O8·2(C5H7N2)·4(H2O) | F(000) = 540 |
Mr = 514.44 | Dx = 1.483 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 8808 reflections |
a = 9.1747 (2) Å | θ = 2.3–32.7° |
b = 17.6168 (4) Å | µ = 0.12 mm−1 |
c = 7.2527 (2) Å | T = 120 K |
β = 100.559 (2)° | Prism, yellow |
V = 1152.40 (5) Å3 | 0.40 × 0.37 × 0.35 mm |
Z = 2 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 4070 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3323 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 32.8°, θmin = 2.3° |
ω scans | h = −13→13 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −26→26 |
Tmin = 0.791, Tmax = 1.000 | l = −10→10 |
24298 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0516P)2 + 0.4163P] where P = (Fo2 + 2Fc2)/3 |
4070 reflections | (Δ/σ)max < 0.001 |
215 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.45 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O1 | 0.83962 (9) | 0.05223 (4) | 0.01699 (10) | 0.01524 (15) | |
O2 | 0.85673 (9) | 0.15808 (4) | 0.18897 (10) | 0.01701 (16) | |
O3 | 0.61389 (8) | 0.03535 (5) | 0.26644 (12) | 0.02116 (17) | |
O4 | 0.62477 (9) | −0.07299 (4) | 0.42927 (12) | 0.02035 (17) | |
O5 | 0.81047 (11) | 0.30139 (5) | 0.04198 (13) | 0.02355 (19) | |
O6 | 0.63988 (10) | 0.39005 (7) | 0.21430 (14) | 0.0363 (3) | |
N1 | 0.19037 (10) | 0.09750 (5) | −0.03108 (12) | 0.01431 (16) | |
N2 | 0.50940 (13) | 0.20528 (7) | 0.1917 (2) | 0.0383 (3) | |
C1 | 0.93188 (10) | 0.04272 (5) | 0.34403 (13) | 0.01025 (16) | |
C2 | 0.84726 (10) | −0.00589 (5) | 0.43541 (13) | 0.01050 (16) | |
C3 | 1.08372 (10) | 0.04825 (5) | 0.41040 (13) | 0.01110 (17) | |
C4 | 0.86790 (10) | 0.08805 (5) | 0.16987 (13) | 0.01091 (17) | |
C5 | 0.68341 (10) | −0.01180 (5) | 0.36839 (13) | 0.01230 (17) | |
C6 | 0.32531 (12) | 0.11347 (6) | 0.06756 (15) | 0.0169 (2) | |
C7 | 0.37589 (12) | 0.18819 (6) | 0.08354 (17) | 0.0211 (2) | |
C8 | 0.28050 (13) | 0.24428 (6) | −0.00871 (18) | 0.0223 (2) | |
C9 | 0.14329 (12) | 0.22483 (6) | −0.11128 (16) | 0.0189 (2) | |
C10 | 0.09809 (11) | 0.15000 (6) | −0.12146 (15) | 0.01611 (19) | |
H1 | 0.1624 (19) | 0.0449 (10) | −0.033 (2) | 0.031 (4)* | |
H2A | 0.575 (3) | 0.1688 (14) | 0.220 (3) | 0.069 (7)* | |
H2B | 0.548 (3) | 0.2537 (14) | 0.183 (3) | 0.061 (6)* | |
H3 | 1.1436 (16) | 0.0810 (8) | 0.345 (2) | 0.016 (3)* | |
H4 | 0.528 (2) | −0.0782 (12) | 0.375 (3) | 0.050 (6)* | |
H5A | 0.817 (2) | 0.2542 (11) | 0.059 (3) | 0.038 (5)* | |
H5B | 0.829 (2) | 0.3107 (10) | −0.071 (3) | 0.039 (5)* | |
H6 | 0.3815 (17) | 0.0718 (9) | 0.124 (2) | 0.023 (4)* | |
H6A | 0.694 (2) | 0.3633 (11) | 0.155 (3) | 0.040 (5)* | |
H6B | 0.696 (3) | 0.4062 (12) | 0.314 (3) | 0.056 (6)* | |
H8 | 0.3133 (19) | 0.2973 (9) | 0.003 (2) | 0.027 (4)* | |
H9 | 0.0794 (19) | 0.2633 (10) | −0.173 (2) | 0.029 (4)* | |
H10 | 0.0043 (18) | 0.1321 (9) | −0.186 (2) | 0.024 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0188 (4) | 0.0136 (3) | 0.0119 (3) | −0.0011 (3) | −0.0011 (3) | 0.0004 (2) |
O2 | 0.0240 (4) | 0.0099 (3) | 0.0157 (3) | 0.0012 (3) | −0.0004 (3) | 0.0018 (2) |
O3 | 0.0116 (3) | 0.0218 (4) | 0.0281 (4) | 0.0009 (3) | −0.0015 (3) | 0.0116 (3) |
O4 | 0.0103 (3) | 0.0176 (3) | 0.0309 (4) | −0.0035 (3) | −0.0023 (3) | 0.0101 (3) |
O5 | 0.0353 (5) | 0.0151 (4) | 0.0224 (4) | 0.0074 (3) | 0.0109 (3) | 0.0043 (3) |
O6 | 0.0173 (4) | 0.0607 (7) | 0.0264 (5) | 0.0180 (4) | −0.0082 (4) | −0.0213 (4) |
N1 | 0.0155 (4) | 0.0125 (3) | 0.0145 (4) | −0.0007 (3) | 0.0014 (3) | −0.0004 (3) |
N2 | 0.0189 (5) | 0.0244 (5) | 0.0630 (9) | −0.0044 (4) | −0.0152 (5) | 0.0030 (5) |
C1 | 0.0105 (4) | 0.0094 (3) | 0.0101 (4) | 0.0009 (3) | −0.0002 (3) | 0.0006 (3) |
C2 | 0.0089 (4) | 0.0097 (3) | 0.0122 (4) | 0.0002 (3) | 0.0002 (3) | 0.0005 (3) |
C3 | 0.0105 (4) | 0.0107 (4) | 0.0118 (4) | −0.0004 (3) | 0.0013 (3) | 0.0018 (3) |
C4 | 0.0095 (4) | 0.0113 (4) | 0.0114 (4) | −0.0007 (3) | 0.0003 (3) | 0.0023 (3) |
C5 | 0.0097 (4) | 0.0129 (4) | 0.0138 (4) | 0.0000 (3) | 0.0010 (3) | 0.0012 (3) |
C6 | 0.0142 (4) | 0.0142 (4) | 0.0210 (5) | 0.0020 (3) | −0.0006 (4) | 0.0015 (3) |
C7 | 0.0139 (4) | 0.0164 (4) | 0.0306 (6) | −0.0009 (4) | −0.0022 (4) | 0.0013 (4) |
C8 | 0.0196 (5) | 0.0129 (4) | 0.0324 (6) | −0.0003 (4) | −0.0002 (4) | 0.0019 (4) |
C9 | 0.0171 (5) | 0.0154 (4) | 0.0232 (5) | 0.0040 (4) | 0.0012 (4) | 0.0031 (4) |
C10 | 0.0136 (4) | 0.0180 (4) | 0.0158 (4) | 0.0002 (3) | 0.0004 (3) | 0.0003 (3) |
Geometric parameters (Å, º) top
O1—C4 | 1.2608 (12) | C1—C4 | 1.5186 (13) |
O2—C4 | 1.2478 (11) | C1—C2 | 1.4014 (13) |
O3—C5 | 1.2127 (12) | C1—C3 | 1.3915 (13) |
O4—C5 | 1.3166 (12) | C2—C3i | 1.3960 (13) |
O4—H4 | 0.908 (19) | C2—C5 | 1.4964 (13) |
O5—H5B | 0.88 (2) | C3—H3 | 0.977 (15) |
O5—H5A | 0.84 (2) | C6—C7 | 1.3935 (15) |
O6—H6A | 0.86 (2) | C7—C8 | 1.4055 (16) |
O6—H6B | 0.86 (2) | C8—C9 | 1.3829 (17) |
N1—C10 | 1.3411 (14) | C9—C10 | 1.3799 (15) |
N1—C6 | 1.3413 (14) | C6—H6 | 0.946 (16) |
N2—C7 | 1.3617 (17) | C8—H8 | 0.982 (16) |
N1—H1 | 0.961 (18) | C9—H9 | 0.952 (17) |
N2—H2A | 0.89 (3) | C10—H10 | 0.955 (16) |
N2—H2B | 0.93 (3) | | |
| | | |
C5—O4—H4 | 111.4 (13) | O3—C5—C2 | 122.36 (8) |
H5A—O5—H5B | 107.4 (18) | O4—C5—C2 | 113.33 (8) |
H6A—O6—H6B | 107 (2) | C1—C3—H3 | 119.3 (9) |
C6—N1—C10 | 123.67 (9) | C2i—C3—H3 | 119.4 (9) |
C6—N1—H1 | 115.3 (10) | N1—C6—C7 | 120.22 (10) |
C10—N1—H1 | 121.0 (10) | N2—C7—C6 | 120.50 (11) |
C7—N2—H2B | 118.5 (15) | N2—C7—C8 | 122.33 (10) |
C7—N2—H2A | 119.1 (16) | C6—C7—C8 | 117.11 (10) |
H2A—N2—H2B | 115 (2) | C7—C8—C9 | 120.53 (10) |
C2—C1—C3 | 119.04 (8) | C8—C9—C10 | 120.04 (10) |
C3—C1—C4 | 117.44 (8) | N1—C10—C9 | 118.43 (10) |
C2—C1—C4 | 123.47 (8) | N1—C6—H6 | 116.4 (10) |
C1—C2—C3i | 119.75 (9) | C7—C6—H6 | 123.4 (10) |
C3i—C2—C5 | 120.28 (8) | C9—C8—H8 | 121.1 (10) |
C1—C2—C5 | 119.97 (8) | C7—C8—H8 | 118.3 (10) |
C1—C3—C2i | 121.21 (8) | C8—C9—H9 | 119.9 (10) |
O1—C4—C1 | 117.01 (8) | C10—C9—H9 | 120.1 (10) |
O2—C4—C1 | 117.05 (8) | C9—C10—H10 | 125.2 (10) |
O1—C4—O2 | 125.78 (9) | N1—C10—H10 | 116.3 (10) |
O3—C5—O4 | 124.31 (9) | | |
| | | |
C10—N1—C6—C7 | 1.21 (16) | C1—C2—C5—O4 | 162.09 (9) |
C6—N1—C10—C9 | −0.70 (16) | C3i—C2—C5—O3 | 162.41 (9) |
C3—C1—C2—C5 | 179.02 (8) | C1—C2—C3i—C1i | 0.56 (14) |
C4—C1—C2—C3i | 176.95 (8) | C5—C2—C3i—C1i | −179.00 (8) |
C2—C1—C3—C2i | 0.56 (14) | C3i—C2—C5—O4 | −18.34 (12) |
C4—C1—C3—C2i | −177.09 (8) | C1—C2—C5—O3 | −17.16 (14) |
C2—C1—C4—O1 | −75.74 (12) | N1—C6—C7—N2 | 176.46 (11) |
C2—C1—C4—O2 | 108.60 (11) | N1—C6—C7—C8 | −0.59 (16) |
C3—C1—C4—O1 | 101.80 (10) | N2—C7—C8—C9 | −177.45 (12) |
C3—C1—C4—O2 | −73.86 (12) | C6—C7—C8—C9 | −0.46 (18) |
C4—C1—C2—C5 | −3.48 (13) | C7—C8—C9—C10 | 0.95 (18) |
C3—C1—C2—C3i | −0.55 (13) | C8—C9—C10—N1 | −0.39 (16) |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.961 (18) | 1.715 (18) | 2.6560 (11) | 165.3 (16) |
N2—H2A···O3 | 0.89 (3) | 2.39 (2) | 3.1598 (15) | 145 (2) |
O4—H4···O6iii | 0.908 (19) | 1.66 (2) | 2.5450 (13) | 166 (2) |
O5—H5A···O2 | 0.84 (2) | 1.94 (2) | 2.7431 (11) | 159 (2) |
O5—H5B···O2iv | 0.88 (2) | 1.89 (2) | 2.7646 (12) | 173.1 (18) |
O6—H6A···O5 | 0.86 (2) | 1.82 (2) | 2.6773 (14) | 176.0 (18) |
O6—H6B···O1v | 0.86 (2) | 1.93 (2) | 2.7816 (13) | 172 (2) |
C6—H6···O3 | 0.946 (16) | 2.284 (16) | 3.0960 (14) | 143.5 (13) |
C8—H8···O4vi | 0.982 (16) | 2.382 (16) | 3.3566 (13) | 171.5 (13) |
C9—H9···O2vii | 0.952 (17) | 2.519 (17) | 3.4453 (13) | 164.3 (14) |
Symmetry codes: (ii) −x+1, −y, −z; (iii) −x+1, y−1/2, −z+1/2; (iv) x, −y+1/2, z−1/2; (v) x, −y+1/2, z+1/2; (vi) −x+1, y+1/2, −z+1/2; (vii) x−1, −y+1/2, z−1/2. |
bis(3-Carboxypyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate (comp2-120K)
top
Crystal data top
C10H4O8·2(C6H6NO2) | F(000) = 516 |
Mr = 500.37 | Dx = 1.640 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 8642 reflections |
a = 7.1378 (1) Å | θ = 2.1–32.8° |
b = 7.3637 (2) Å | µ = 0.14 mm−1 |
c = 19.3563 (4) Å | T = 120 K |
β = 95.135 (2)° | Prism, colourless |
V = 1013.30 (4) Å3 | 0.20 × 0.15 × 0.15 mm |
Z = 2 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 3567 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3050 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 32.9°, θmin = 2.1° |
ω scans | h = −10→10 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −11→11 |
Tmin = 0.972, Tmax = 1.000 | l = −29→29 |
21726 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.109 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0584P)2 + 0.3182P] where P = (Fo2 + 2Fc2)/3 |
3567 reflections | (Δ/σ)max < 0.001 |
195 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O1 | 0.25710 (10) | 0.75021 (11) | 0.12671 (4) | 0.01696 (16) | |
O2 | 0.05453 (10) | 0.74158 (11) | 0.03409 (4) | 0.01869 (16) | |
O3 | 0.17308 (11) | 1.01155 (13) | −0.15468 (4) | 0.02193 (18) | |
O4 | 0.02536 (10) | 0.83892 (11) | −0.08388 (4) | 0.01902 (17) | |
O5 | 0.27915 (11) | 0.27053 (12) | 0.15897 (4) | 0.01941 (17) | |
O6 | 0.32504 (11) | 0.37457 (11) | 0.05290 (4) | 0.01814 (16) | |
N1 | 0.84877 (12) | 0.56540 (12) | 0.12574 (5) | 0.01554 (17) | |
C1 | 0.35179 (12) | 0.89898 (12) | 0.02635 (5) | 0.01065 (16) | |
C2 | 0.33136 (12) | 0.96285 (12) | −0.04286 (5) | 0.01065 (16) | |
C3 | 0.51940 (12) | 0.93934 (13) | 0.06625 (5) | 0.01118 (16) | |
C4 | 0.21506 (13) | 0.79072 (13) | 0.06594 (5) | 0.01223 (17) | |
C5 | 0.16722 (13) | 0.93926 (13) | −0.09830 (5) | 0.01303 (18) | |
C6 | 0.67725 (14) | 0.50849 (13) | 0.10105 (5) | 0.01394 (18) | |
C7 | 0.56438 (13) | 0.41914 (13) | 0.14455 (5) | 0.01201 (17) | |
C8 | 0.63105 (14) | 0.39054 (14) | 0.21354 (5) | 0.01529 (18) | |
C9 | 0.81023 (14) | 0.45138 (15) | 0.23723 (5) | 0.01689 (19) | |
C10 | 0.91780 (14) | 0.53906 (14) | 0.19180 (5) | 0.01650 (19) | |
C11 | 0.37718 (13) | 0.35401 (13) | 0.11369 (5) | 0.01308 (17) | |
H1 | 0.918 (2) | 0.624 (2) | 0.0952 (9) | 0.029 (4)* | |
H3 | 0.5328 (19) | 0.8973 (19) | 0.1131 (7) | 0.014 (3)* | |
H4 | 0.037 (3) | 0.792 (3) | −0.0246 (12) | 0.066 (7)* | |
H5 | 0.172 (3) | 0.229 (3) | 0.1356 (11) | 0.048 (5)* | |
H6 | 0.638 (2) | 0.531 (2) | 0.0535 (8) | 0.019 (3)* | |
H8 | 0.554 (2) | 0.328 (2) | 0.2456 (7) | 0.017 (3)* | |
H9 | 0.864 (2) | 0.433 (2) | 0.2845 (8) | 0.026 (4)* | |
H10 | 1.049 (2) | 0.585 (2) | 0.2020 (8) | 0.025 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0155 (3) | 0.0225 (4) | 0.0130 (3) | −0.0049 (3) | 0.0022 (2) | 0.0014 (3) |
O2 | 0.0116 (3) | 0.0268 (4) | 0.0173 (3) | −0.0090 (3) | −0.0009 (3) | 0.0034 (3) |
O3 | 0.0155 (3) | 0.0326 (4) | 0.0165 (4) | −0.0063 (3) | −0.0048 (3) | 0.0067 (3) |
O4 | 0.0124 (3) | 0.0260 (4) | 0.0177 (3) | −0.0089 (3) | −0.0042 (3) | 0.0034 (3) |
O5 | 0.0132 (3) | 0.0291 (4) | 0.0155 (3) | −0.0099 (3) | −0.0011 (3) | 0.0030 (3) |
O6 | 0.0170 (3) | 0.0233 (4) | 0.0133 (3) | −0.0036 (3) | −0.0031 (3) | 0.0012 (3) |
N1 | 0.0131 (4) | 0.0160 (4) | 0.0178 (4) | −0.0038 (3) | 0.0027 (3) | 0.0016 (3) |
C1 | 0.0080 (3) | 0.0120 (4) | 0.0120 (4) | −0.0015 (3) | 0.0008 (3) | −0.0012 (3) |
C2 | 0.0078 (3) | 0.0121 (4) | 0.0118 (4) | −0.0007 (3) | −0.0003 (3) | −0.0012 (3) |
C3 | 0.0089 (4) | 0.0129 (4) | 0.0115 (4) | −0.0010 (3) | 0.0000 (3) | −0.0001 (3) |
C4 | 0.0093 (4) | 0.0134 (4) | 0.0142 (4) | −0.0025 (3) | 0.0024 (3) | −0.0012 (3) |
C5 | 0.0087 (4) | 0.0150 (4) | 0.0148 (4) | −0.0009 (3) | −0.0021 (3) | −0.0012 (3) |
C6 | 0.0136 (4) | 0.0147 (4) | 0.0134 (4) | −0.0016 (3) | 0.0004 (3) | 0.0016 (3) |
C7 | 0.0101 (4) | 0.0136 (4) | 0.0120 (4) | −0.0017 (3) | −0.0006 (3) | 0.0001 (3) |
C8 | 0.0136 (4) | 0.0189 (4) | 0.0132 (4) | −0.0038 (3) | 0.0000 (3) | 0.0020 (3) |
C9 | 0.0147 (4) | 0.0200 (5) | 0.0152 (4) | −0.0029 (3) | −0.0032 (3) | 0.0005 (3) |
C10 | 0.0127 (4) | 0.0170 (4) | 0.0194 (5) | −0.0031 (3) | −0.0009 (3) | −0.0010 (3) |
C11 | 0.0113 (4) | 0.0140 (4) | 0.0137 (4) | −0.0015 (3) | 0.0000 (3) | −0.0005 (3) |
Geometric parameters (Å, º) top
O1—C4 | 1.2245 (12) | C1—C4 | 1.5196 (13) |
O2—C4 | 1.3029 (12) | C2—C5 | 1.5262 (13) |
O3—C5 | 1.2183 (13) | C2—C3i | 1.3946 (13) |
O4—C5 | 1.3037 (12) | C3—H3 | 0.955 (14) |
O2—H4 | 1.19 (2) | C6—C7 | 1.3829 (14) |
O4—H4 | 1.19 (2) | C7—C8 | 1.3930 (14) |
O5—C11 | 1.3212 (12) | C7—C11 | 1.4931 (13) |
O6—C11 | 1.2114 (12) | C8—C9 | 1.3935 (14) |
O5—H5 | 0.91 (2) | C9—C10 | 1.3786 (14) |
N1—C10 | 1.3426 (14) | C6—H6 | 0.952 (15) |
N1—C6 | 1.3409 (13) | C8—H8 | 0.980 (14) |
N1—H1 | 0.912 (16) | C9—H9 | 0.970 (15) |
C1—C3 | 1.3967 (13) | C10—H10 | 0.999 (15) |
C1—C2 | 1.4150 (14) | | |
| | | |
C4—O2—H4 | 112.2 (10) | C1—C3—H3 | 117.7 (8) |
C5—O4—H4 | 112.4 (10) | N1—C6—C7 | 119.65 (9) |
C11—O5—H5 | 107.4 (14) | C6—C7—C8 | 119.21 (9) |
C6—N1—C10 | 122.67 (9) | C6—C7—C11 | 117.29 (9) |
C6—N1—H1 | 116.6 (10) | C8—C7—C11 | 123.48 (9) |
C10—N1—H1 | 120.8 (10) | C7—C8—C9 | 119.45 (9) |
C3—C1—C4 | 112.94 (8) | C8—C9—C10 | 119.20 (9) |
C2—C1—C4 | 129.45 (8) | N1—C10—C9 | 119.82 (9) |
C2—C1—C3 | 117.61 (8) | O5—C11—O6 | 124.58 (9) |
C1—C2—C3i | 117.52 (8) | O5—C11—C7 | 113.09 (8) |
C1—C2—C5 | 129.45 (8) | O6—C11—C7 | 122.31 (9) |
C3i—C2—C5 | 113.02 (8) | N1—C6—H6 | 118.1 (9) |
C1—C3—C2i | 124.87 (9) | C7—C6—H6 | 122.3 (9) |
O2—C4—C1 | 118.97 (8) | C7—C8—H8 | 121.0 (8) |
O1—C4—O2 | 121.09 (9) | C9—C8—H8 | 119.6 (8) |
O1—C4—C1 | 119.93 (8) | C8—C9—H9 | 122.7 (9) |
O3—C5—C2 | 119.63 (9) | C10—C9—H9 | 118.1 (9) |
O3—C5—O4 | 121.94 (9) | N1—C10—H10 | 113.4 (9) |
O4—C5—C2 | 118.43 (8) | C9—C10—H10 | 126.8 (9) |
C2i—C3—H3 | 117.5 (8) | | |
| | | |
C10—N1—C6—C7 | 0.16 (15) | C1—C2—C3i—C1i | −0.35 (14) |
C6—N1—C10—C9 | −0.45 (15) | C5—C2—C3i—C1i | −179.68 (9) |
C3—C1—C2—C5 | 179.53 (9) | C3i—C2—C5—O4 | 175.16 (9) |
C4—C1—C2—C3i | 179.78 (9) | C1—C2—C5—O3 | 177.01 (10) |
C2—C1—C3—C2i | −0.35 (14) | N1—C6—C7—C8 | 0.27 (14) |
C4—C1—C3—C2i | −179.89 (9) | N1—C6—C7—C11 | −178.21 (9) |
C2—C1—C4—O1 | −178.67 (9) | C6—C7—C8—C9 | −0.39 (15) |
C2—C1—C4—O2 | 1.73 (15) | C11—C7—C8—C9 | 177.99 (9) |
C3—C1—C4—O1 | 0.81 (13) | C6—C7—C11—O5 | −179.95 (9) |
C3—C1—C4—O2 | −178.79 (9) | C6—C7—C11—O6 | 1.22 (14) |
C4—C1—C2—C5 | −1.02 (16) | C8—C7—C11—O5 | 1.64 (14) |
C3—C1—C2—C3i | 0.32 (13) | C8—C7—C11—O6 | −177.19 (10) |
C1—C2—C5—O4 | −4.08 (15) | C7—C8—C9—C10 | 0.11 (15) |
C3i—C2—C5—O3 | −3.75 (13) | C8—C9—C10—N1 | 0.30 (16) |
Symmetry code: (i) −x+1, −y+2, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ii | 0.912 (16) | 1.818 (16) | 2.7301 (12) | 180 (2) |
O4—H4···O2 | 1.19 (2) | 1.19 (2) | 2.3846 (11) | 177.5 (19) |
O5—H5···O4iii | 0.91 (2) | 1.73 (2) | 2.6308 (11) | 174.3 (19) |
C6—H6···O6iv | 0.952 (15) | 2.212 (15) | 3.1005 (12) | 154.9 (12) |
C9—H9···O1v | 0.970 (15) | 2.404 (15) | 3.0964 (13) | 128.0 (11) |
C9—H9···O3vi | 0.970 (15) | 2.440 (15) | 3.1921 (13) | 134.1 (11) |
C10—H10···O1ii | 0.999 (15) | 2.490 (15) | 3.2275 (13) | 130.4 (11) |
Symmetry codes: (ii) x+1, y, z; (iii) −x, −y+1, −z; (iv) −x+1, −y+1, −z; (v) −x+1, y−1/2, −z+1/2; (vi) x+1, −y+3/2, z+1/2. |
bis(3-Carboxyphenylammonium) 2,5-dicarboxybenzene-1,4-dicarboxylate dihydrate (comp3-120K)
top
Crystal data top
C10H4O8·2(C7H8NO2)·2(H2O) | Z = 1 |
Mr = 564.45 | F(000) = 294 |
Triclinic, P1 | Dx = 1.622 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 7.3815 (4) Å | Cell parameters from 3894 reflections |
b = 7.7144 (4) Å | θ = 2.0–32.7° |
c = 10.3085 (5) Å | µ = 0.14 mm−1 |
α = 79.986 (4)° | T = 120 K |
β = 89.329 (4)° | Prism, colourless |
γ = 88.548 (4)° | 0.42 × 0.40 × 0.40 mm |
V = 577.86 (5) Å3 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 3928 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3087 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 32.8°, θmin = 2.7° |
ω scans | h = −11→11 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −11→11 |
Tmin = 0.829, Tmax = 1.000 | l = −15→15 |
12130 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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0646P)2 + 0.0629P] where P = (Fo2 + 2Fc2)/3 |
3928 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O1 | 0.10465 (12) | 0.57019 (11) | 0.32806 (8) | 0.01996 (19) | |
O2 | −0.04644 (12) | 0.81330 (11) | 0.24657 (8) | 0.02060 (19) | |
O3 | −0.24830 (12) | 0.89382 (11) | −0.15045 (8) | 0.01999 (19) | |
O4 | −0.19674 (12) | 0.94565 (11) | 0.04860 (9) | 0.0229 (2) | |
O5 | 0.40680 (13) | 0.79781 (12) | 0.16574 (8) | 0.02139 (19) | |
O6 | 0.50379 (12) | 0.81224 (11) | 0.36873 (8) | 0.02097 (19) | |
O7 | 0.75764 (13) | 0.87308 (12) | 0.56782 (9) | 0.0229 (2) | |
N1 | 0.87506 (14) | 0.22946 (13) | 0.48354 (10) | 0.0163 (2) | |
C1 | 0.00394 (14) | 0.59148 (14) | 0.10808 (10) | 0.01165 (19) | |
C2 | −0.08402 (14) | 0.67001 (13) | −0.00929 (10) | 0.0120 (2) | |
C3 | 0.08425 (14) | 0.42525 (14) | 0.11249 (10) | 0.0128 (2) | |
C4 | 0.02246 (15) | 0.66291 (14) | 0.23546 (10) | 0.0144 (2) | |
C5 | −0.18184 (14) | 0.84767 (14) | −0.03952 (11) | 0.0141 (2) | |
C6 | 0.75688 (14) | 0.31118 (14) | 0.37648 (10) | 0.0134 (2) | |
C7 | 0.67982 (15) | 0.47539 (14) | 0.38048 (10) | 0.0136 (2) | |
C8 | 0.57052 (14) | 0.55383 (14) | 0.27605 (10) | 0.0132 (2) | |
C9 | 0.53903 (15) | 0.46541 (15) | 0.17169 (11) | 0.0161 (2) | |
C10 | 0.61706 (16) | 0.29967 (15) | 0.16998 (11) | 0.0172 (2) | |
C11 | 0.72723 (15) | 0.22180 (15) | 0.27304 (11) | 0.0157 (2) | |
C12 | 0.49141 (15) | 0.73369 (15) | 0.27593 (11) | 0.0150 (2) | |
H1A | 0.833 (2) | 0.116 (2) | 0.5207 (16) | 0.029 (4)* | |
H1B | 0.993 (2) | 0.218 (2) | 0.4553 (16) | 0.029 (4)* | |
H1C | 0.879 (2) | 0.301 (2) | 0.5518 (17) | 0.033 (4)* | |
H3 | 0.137 (2) | 0.373 (2) | 0.1916 (15) | 0.021 (4)* | |
H4 | −0.127 (4) | 0.877 (4) | 0.149 (3) | 0.090 (9)* | |
H5 | 0.360 (3) | 0.904 (3) | 0.170 (2) | 0.053 (6)* | |
H7 | 0.7029 (18) | 0.5363 (19) | 0.4569 (14) | 0.017 (3)* | |
H7A | 0.664 (3) | 0.849 (3) | 0.513 (2) | 0.071 (7)* | |
H7B | 0.717 (3) | 0.863 (3) | 0.646 (3) | 0.066 (7)* | |
H9 | 0.461 (2) | 0.517 (2) | 0.1049 (15) | 0.023 (4)* | |
H10 | 0.594 (2) | 0.239 (2) | 0.0956 (16) | 0.029 (4)* | |
H11 | 0.783 (2) | 0.106 (2) | 0.2772 (16) | 0.028 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0276 (4) | 0.0190 (4) | 0.0142 (4) | 0.0068 (3) | −0.0070 (3) | −0.0059 (3) |
O2 | 0.0314 (5) | 0.0149 (4) | 0.0172 (4) | 0.0078 (3) | −0.0058 (3) | −0.0086 (3) |
O3 | 0.0279 (4) | 0.0145 (4) | 0.0175 (4) | 0.0075 (3) | −0.0081 (3) | −0.0029 (3) |
O4 | 0.0341 (5) | 0.0154 (4) | 0.0208 (4) | 0.0126 (3) | −0.0075 (4) | −0.0088 (3) |
O5 | 0.0313 (5) | 0.0149 (4) | 0.0174 (4) | 0.0102 (3) | −0.0076 (3) | −0.0023 (3) |
O6 | 0.0274 (4) | 0.0178 (4) | 0.0190 (4) | 0.0073 (3) | −0.0047 (3) | −0.0076 (3) |
O7 | 0.0267 (5) | 0.0212 (5) | 0.0210 (5) | 0.0053 (4) | −0.0008 (4) | −0.0051 (3) |
N1 | 0.0205 (5) | 0.0146 (5) | 0.0146 (4) | 0.0058 (4) | −0.0061 (3) | −0.0048 (3) |
C1 | 0.0132 (4) | 0.0098 (4) | 0.0123 (4) | 0.0008 (3) | −0.0014 (3) | −0.0032 (3) |
C2 | 0.0134 (5) | 0.0093 (4) | 0.0131 (5) | 0.0015 (3) | −0.0015 (4) | −0.0019 (4) |
C3 | 0.0152 (5) | 0.0114 (5) | 0.0118 (5) | 0.0021 (4) | −0.0024 (4) | −0.0022 (4) |
C4 | 0.0171 (5) | 0.0138 (5) | 0.0131 (5) | 0.0002 (4) | −0.0012 (4) | −0.0045 (4) |
C5 | 0.0156 (5) | 0.0105 (5) | 0.0162 (5) | 0.0027 (4) | −0.0018 (4) | −0.0022 (4) |
C6 | 0.0152 (5) | 0.0133 (5) | 0.0114 (4) | 0.0035 (4) | −0.0029 (3) | −0.0020 (4) |
C7 | 0.0169 (5) | 0.0125 (5) | 0.0115 (4) | 0.0028 (4) | −0.0015 (4) | −0.0029 (4) |
C8 | 0.0142 (5) | 0.0125 (5) | 0.0129 (5) | 0.0033 (4) | −0.0008 (4) | −0.0026 (4) |
C9 | 0.0176 (5) | 0.0172 (5) | 0.0136 (5) | 0.0032 (4) | −0.0040 (4) | −0.0031 (4) |
C10 | 0.0217 (5) | 0.0165 (5) | 0.0149 (5) | 0.0020 (4) | −0.0034 (4) | −0.0066 (4) |
C11 | 0.0200 (5) | 0.0120 (5) | 0.0157 (5) | 0.0031 (4) | −0.0023 (4) | −0.0045 (4) |
C12 | 0.0161 (5) | 0.0135 (5) | 0.0150 (5) | 0.0026 (4) | −0.0004 (4) | −0.0019 (4) |
Geometric parameters (Å, º) top
O1—C4 | 1.2430 (13) | C1—C4 | 1.5186 (15) |
O2—C4 | 1.2778 (14) | C1—C2 | 1.4128 (14) |
O3—C5 | 1.2401 (14) | C2—C5 | 1.5177 (15) |
O4—C5 | 1.2809 (14) | C2—C3i | 1.3942 (15) |
O2—H4 | 1.20 (3) | C3—H3 | 0.930 (15) |
O4—H4 | 1.19 (3) | C6—C11 | 1.3889 (15) |
O5—C12 | 1.3155 (14) | C6—C7 | 1.3824 (15) |
O6—C12 | 1.2236 (14) | C7—C8 | 1.3946 (15) |
O5—H5 | 0.89 (2) | C8—C12 | 1.4915 (16) |
O7—H7A | 0.94 (2) | C8—C9 | 1.3949 (15) |
O7—H7B | 0.85 (3) | C9—C10 | 1.3918 (17) |
N1—C6 | 1.4592 (15) | C10—C11 | 1.3872 (16) |
N1—H1A | 0.951 (16) | C7—H7 | 1.003 (15) |
N1—H1C | 0.968 (17) | C9—H9 | 0.931 (15) |
N1—H1B | 0.922 (15) | C10—H10 | 0.984 (16) |
C1—C3 | 1.3928 (15) | C11—H11 | 0.968 (16) |
| | | |
C4—O2—H4 | 110.9 (15) | C1—C3—H3 | 117.0 (10) |
C5—O4—H4 | 111.1 (15) | C2i—C3—H3 | 118.3 (10) |
C12—O5—H5 | 110.0 (13) | N1—C6—C7 | 119.09 (9) |
H7A—O7—H7B | 108 (2) | N1—C6—C11 | 118.72 (10) |
C6—N1—H1C | 110.8 (9) | C7—C6—C11 | 122.19 (10) |
H1B—N1—H1C | 106.1 (13) | C6—C7—C8 | 118.52 (10) |
H1A—N1—H1B | 108.6 (13) | C7—C8—C9 | 119.94 (10) |
H1A—N1—H1C | 109.0 (14) | C9—C8—C12 | 120.61 (10) |
C6—N1—H1B | 111.9 (10) | C7—C8—C12 | 119.44 (9) |
C6—N1—H1A | 110.3 (9) | C8—C9—C10 | 120.62 (10) |
C2—C1—C4 | 128.66 (10) | C9—C10—C11 | 119.65 (11) |
C3—C1—C4 | 113.44 (9) | C6—C11—C10 | 119.08 (11) |
C2—C1—C3 | 117.90 (9) | O5—C12—O6 | 123.91 (11) |
C1—C2—C5 | 128.47 (9) | O6—C12—C8 | 123.40 (10) |
C1—C2—C3i | 117.38 (9) | O5—C12—C8 | 112.69 (10) |
C3i—C2—C5 | 114.15 (9) | C6—C7—H7 | 120.4 (8) |
C1—C3—C2i | 124.72 (10) | C8—C7—H7 | 121.1 (8) |
O1—C4—C1 | 118.04 (10) | C10—C9—H9 | 120.5 (10) |
O1—C4—O2 | 121.45 (10) | C8—C9—H9 | 118.9 (10) |
O2—C4—C1 | 120.52 (9) | C9—C10—H10 | 119.8 (9) |
O4—C5—C2 | 120.37 (10) | C11—C10—H10 | 120.6 (9) |
O3—C5—C2 | 118.38 (10) | C6—C11—H11 | 118.1 (10) |
O3—C5—O4 | 121.24 (10) | C10—C11—H11 | 122.8 (9) |
| | | |
C3—C1—C2—C5 | 179.72 (10) | C5—C2—C3i—C1i | −179.78 (10) |
C3—C1—C2—C3i | 0.11 (15) | N1—C6—C7—C8 | 178.53 (10) |
C4—C1—C2—C5 | 0.66 (18) | C11—C6—C7—C8 | −0.75 (16) |
C4—C1—C2—C3i | −178.95 (10) | N1—C6—C11—C10 | −179.12 (10) |
C2—C1—C3—C2i | −0.12 (16) | C7—C6—C11—C10 | 0.16 (17) |
C4—C1—C3—C2i | 179.08 (10) | C6—C7—C8—C9 | 0.94 (16) |
C2—C1—C4—O1 | 179.23 (11) | C6—C7—C8—C12 | −177.80 (10) |
C2—C1—C4—O2 | −0.10 (17) | C7—C8—C9—C10 | −0.57 (16) |
C3—C1—C4—O1 | 0.14 (15) | C12—C8—C9—C10 | 178.16 (10) |
C3—C1—C4—O2 | −179.19 (10) | C7—C8—C12—O5 | 173.62 (10) |
C1—C2—C5—O3 | 178.91 (11) | C7—C8—C12—O6 | −6.60 (17) |
C1—C2—C5—O4 | −1.98 (17) | C9—C8—C12—O5 | −5.11 (15) |
C3i—C2—C5—O3 | −1.48 (14) | C9—C8—C12—O6 | 174.67 (11) |
C3i—C2—C5—O4 | 177.64 (10) | C8—C9—C10—C11 | −0.03 (17) |
C1—C2—C3i—C1i | −0.12 (16) | C9—C10—C11—C6 | 0.23 (17) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O7ii | 0.951 (16) | 1.946 (16) | 2.8874 (14) | 170.2 (14) |
N1—H1B···O7iii | 0.922 (15) | 1.980 (15) | 2.8740 (14) | 162.9 (14) |
N1—H1C···O1iv | 0.968 (17) | 1.724 (16) | 2.6918 (13) | 177.6 (14) |
O4—H4···O2 | 1.19 (3) | 1.20 (3) | 2.3894 (12) | 176 (3) |
O5—H5···O3v | 0.89 (2) | 1.73 (2) | 2.6049 (13) | 169 (2) |
O7—H7A···O6 | 0.94 (2) | 1.97 (2) | 2.9005 (13) | 168.3 (19) |
O7—H7B···O3vi | 0.85 (3) | 2.17 (3) | 2.9360 (12) | 150 (2) |
Symmetry codes: (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x, −y+2, −z; (vi) x+1, y, z+1. |
bis(4-Carboxyphenylammonium) 2,5-dicarboxybenzene-1,4-dicarboxylate (comp4-120K)
top
Crystal data top
C10H4O8·2(C7H8NO2) | Z = 1 |
Mr = 528.42 | F(000) = 274 |
Triclinic, P1 | Dx = 1.579 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 6.5293 (3) Å | Cell parameters from 4767 reflections |
b = 9.5176 (5) Å | θ = 2.3–32.6° |
c = 9.8073 (5) Å | µ = 0.13 mm−1 |
α = 66.586 (5)° | T = 120 K |
β = 88.062 (4)° | Prism, colourless |
γ = 83.612 (4)° | 0.40 × 0.35 × 0.33 mm |
V = 555.77 (5) Å3 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 3772 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3071 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 32.7°, θmin = 2.3° |
ω scans | h = −9→9 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −13→14 |
Tmin = 0.939, Tmax = 1.000 | l = −14→14 |
12081 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0593P)2 + 0.163P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
3772 reflections | Δρmax = 0.46 e Å−3 |
213 parameters | Δρmin = −0.30 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.127 (10) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O1 | 0.84566 (12) | 0.06539 (10) | 0.83275 (8) | 0.01825 (18) | |
O2 | 0.56155 (12) | 0.11083 (9) | 0.69371 (9) | 0.01716 (18) | |
O3 | 0.88876 (14) | 0.34832 (9) | 0.57461 (10) | 0.0234 (2) | |
O4 | 1.14835 (14) | 0.38115 (10) | 0.41454 (11) | 0.0262 (2) | |
O5 | 0.55634 (17) | 0.61439 (11) | 0.30110 (11) | 0.0311 (2) | |
O6 | 0.69855 (17) | 0.74319 (11) | 0.08195 (13) | 0.0349 (3) | |
N1 | 0.74600 (15) | 0.05068 (11) | 0.10905 (10) | 0.01525 (19) | |
C1 | 0.88046 (15) | 0.04174 (11) | 0.60260 (10) | 0.01091 (18) | |
C2 | 1.00866 (15) | 0.14365 (10) | 0.50364 (11) | 0.01111 (19) | |
C3 | 1.12661 (15) | 0.10156 (11) | 0.40221 (11) | 0.01172 (19) | |
C4 | 0.75210 (15) | 0.07801 (11) | 0.71838 (11) | 0.01217 (19) | |
C5 | 1.01017 (16) | 0.30053 (11) | 0.50167 (11) | 0.01321 (19) | |
C6 | 0.72121 (15) | 0.19754 (12) | 0.12514 (12) | 0.0140 (2) | |
C7 | 0.63785 (16) | 0.20220 (13) | 0.25558 (12) | 0.0155 (2) | |
C8 | 0.61578 (17) | 0.34051 (13) | 0.27347 (12) | 0.0168 (2) | |
C9 | 0.67765 (16) | 0.47289 (13) | 0.16121 (13) | 0.0172 (2) | |
C10 | 0.76135 (17) | 0.46609 (13) | 0.03092 (13) | 0.0192 (2) | |
C11 | 0.78494 (17) | 0.32785 (13) | 0.01249 (12) | 0.0177 (2) | |
C12 | 0.64813 (17) | 0.62401 (13) | 0.17545 (14) | 0.0207 (2) | |
H1A | 0.880 (3) | −0.001 (2) | 0.1449 (18) | 0.031 (4)* | |
H1B | 0.745 (3) | 0.066 (2) | 0.007 (2) | 0.037 (5)* | |
H1C | 0.646 (3) | −0.009 (2) | 0.1585 (19) | 0.032 (4)* | |
H3 | 1.210 (2) | 0.1727 (17) | 0.3345 (15) | 0.015 (3)* | |
H4 | 1.144 (3) | 0.475 (3) | 0.421 (2) | 0.063 (7)* | |
H5 | 0.527 (3) | 0.714 (3) | 0.298 (2) | 0.062 (6)* | |
H7 | 0.599 (2) | 0.1083 (18) | 0.3314 (17) | 0.022 (4)* | |
H8 | 0.561 (2) | 0.3435 (19) | 0.3647 (18) | 0.027 (4)* | |
H10 | 0.797 (2) | 0.5610 (18) | −0.0483 (17) | 0.020 (4)* | |
H11 | 0.844 (3) | 0.3200 (19) | −0.0786 (18) | 0.028 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0209 (4) | 0.0226 (4) | 0.0141 (3) | 0.0012 (3) | 0.0021 (3) | −0.0113 (3) |
O2 | 0.0147 (4) | 0.0167 (4) | 0.0245 (4) | −0.0014 (3) | 0.0048 (3) | −0.0131 (3) |
O3 | 0.0310 (5) | 0.0135 (4) | 0.0323 (5) | −0.0091 (3) | 0.0188 (4) | −0.0159 (3) |
O4 | 0.0333 (5) | 0.0150 (4) | 0.0389 (5) | −0.0138 (3) | 0.0238 (4) | −0.0185 (4) |
O5 | 0.0456 (6) | 0.0185 (4) | 0.0319 (5) | 0.0038 (4) | 0.0080 (4) | −0.0154 (4) |
O6 | 0.0413 (6) | 0.0222 (5) | 0.0480 (6) | −0.0122 (4) | 0.0175 (5) | −0.0200 (4) |
N1 | 0.0165 (4) | 0.0168 (4) | 0.0159 (4) | −0.0013 (3) | 0.0025 (3) | −0.0104 (3) |
C1 | 0.0125 (4) | 0.0098 (4) | 0.0120 (4) | −0.0004 (3) | 0.0018 (3) | −0.0063 (3) |
C2 | 0.0133 (4) | 0.0077 (4) | 0.0142 (4) | −0.0012 (3) | 0.0020 (3) | −0.0065 (3) |
C3 | 0.0141 (4) | 0.0094 (4) | 0.0131 (4) | −0.0024 (3) | 0.0039 (3) | −0.0060 (3) |
C4 | 0.0163 (4) | 0.0077 (4) | 0.0143 (4) | −0.0028 (3) | 0.0053 (3) | −0.0062 (3) |
C5 | 0.0173 (5) | 0.0093 (4) | 0.0152 (4) | −0.0029 (3) | 0.0038 (3) | −0.0071 (3) |
C6 | 0.0123 (4) | 0.0158 (4) | 0.0163 (4) | 0.0004 (3) | −0.0003 (3) | −0.0095 (4) |
C7 | 0.0154 (5) | 0.0174 (5) | 0.0150 (4) | 0.0001 (4) | 0.0011 (4) | −0.0085 (4) |
C8 | 0.0159 (5) | 0.0195 (5) | 0.0183 (5) | 0.0013 (4) | 0.0006 (4) | −0.0118 (4) |
C9 | 0.0133 (4) | 0.0168 (5) | 0.0246 (5) | 0.0008 (4) | −0.0007 (4) | −0.0120 (4) |
C10 | 0.0171 (5) | 0.0182 (5) | 0.0235 (5) | −0.0033 (4) | 0.0030 (4) | −0.0095 (4) |
C11 | 0.0170 (5) | 0.0197 (5) | 0.0186 (5) | −0.0027 (4) | 0.0039 (4) | −0.0101 (4) |
C12 | 0.0164 (5) | 0.0196 (5) | 0.0309 (6) | 0.0005 (4) | −0.0002 (4) | −0.0155 (5) |
Geometric parameters (Å, º) top
O1—C4 | 1.2525 (13) | C1—C3i | 1.3892 (16) |
O2—C4 | 1.2561 (13) | C1—C4 | 1.5145 (14) |
O3—C5 | 1.2194 (14) | C3—H3 | 0.947 (15) |
O4—C5 | 1.3091 (14) | C6—C7 | 1.3883 (16) |
O4—H4 | 0.92 (3) | C6—C11 | 1.3881 (16) |
O5—C12 | 1.3262 (16) | C7—C8 | 1.3871 (19) |
O6—C12 | 1.2132 (17) | C8—C9 | 1.3941 (17) |
O5—H5 | 0.94 (3) | C9—C12 | 1.4905 (19) |
N1—C6 | 1.4588 (17) | C9—C10 | 1.3951 (17) |
N1—H1B | 0.943 (18) | C10—C11 | 1.3891 (19) |
N1—H1A | 0.959 (19) | C7—H7 | 0.962 (16) |
N1—H1C | 0.909 (19) | C8—H8 | 0.962 (17) |
C1—C2 | 1.4003 (14) | C10—H10 | 0.975 (16) |
C2—C5 | 1.4867 (15) | C11—H11 | 0.988 (17) |
C2—C3 | 1.3926 (14) | | |
| | | |
C5—O4—H4 | 110.0 (12) | N1—C6—C7 | 118.62 (10) |
C12—O5—H5 | 108.2 (11) | N1—C6—C11 | 119.81 (10) |
C6—N1—H1C | 111.0 (13) | C7—C6—C11 | 121.56 (12) |
H1A—N1—H1B | 104.5 (16) | C6—C7—C8 | 119.34 (11) |
H1B—N1—H1C | 110.2 (17) | C7—C8—C9 | 119.97 (11) |
C6—N1—H1A | 109.3 (12) | C8—C9—C10 | 119.93 (12) |
H1A—N1—H1C | 110.7 (16) | C8—C9—C12 | 120.93 (11) |
C6—N1—H1B | 110.9 (12) | C10—C9—C12 | 119.09 (11) |
C3—C2—C5 | 119.89 (9) | C9—C10—C11 | 120.44 (11) |
C1—C2—C5 | 119.69 (9) | C6—C11—C10 | 118.75 (11) |
C3i—C1—C4 | 117.84 (9) | O5—C12—O6 | 123.54 (13) |
C2—C1—C3i | 118.89 (9) | O5—C12—C9 | 112.31 (11) |
C2—C1—C4 | 123.25 (10) | O6—C12—C9 | 124.14 (12) |
C2—C3—C1i | 120.78 (9) | C6—C7—H7 | 118.5 (10) |
O1—C4—C1 | 116.49 (9) | C8—C7—H7 | 122.2 (10) |
O2—C4—C1 | 117.07 (9) | C7—C8—H8 | 119.5 (11) |
O1—C4—O2 | 126.35 (10) | C9—C8—H8 | 120.5 (11) |
O3—C5—C2 | 121.53 (10) | C9—C10—H10 | 118.6 (10) |
O4—C5—C2 | 114.53 (9) | C11—C10—H10 | 120.9 (10) |
O3—C5—O4 | 123.93 (11) | C6—C11—H11 | 119.3 (11) |
C1i—C3—H3 | 119.9 (10) | C10—C11—H11 | 122.0 (11) |
C2—C3—H3 | 119.3 (10) | | |
| | | |
C5—C2—C1—C3 | 176.83 (9) | C3i—C1—C4—O2 | −76.17 (13) |
C5—C2—C1—C4 | −4.84 (15) | N1—C6—C7—C8 | 179.15 (10) |
C3i—C2—C1—C3 | 0.07 (13) | C11—C6—C7—C8 | 0.61 (16) |
C3i—C2—C1—C4 | 178.41 (9) | N1—C6—C11—C10 | −179.46 (10) |
C1—C2—C5—O3 | −6.79 (15) | C7—C6—C11—C10 | −0.94 (16) |
C1—C2—C5—O4 | 174.27 (9) | C6—C7—C8—C9 | −0.19 (16) |
C3—C2—C5—O3 | 169.98 (10) | C7—C8—C9—C10 | 0.11 (16) |
C3—C2—C5—O4 | −8.96 (14) | C7—C8—C9—C12 | 177.66 (10) |
C1—C2—C3—C1i | −0.07 (14) | C8—C9—C10—C11 | −0.45 (17) |
C5—C2—C3—C1i | −176.82 (9) | C12—C9—C10—C11 | −178.04 (10) |
C2—C1—C3i—C2i | −0.07 (13) | C8—C9—C12—O5 | −1.28 (15) |
C4—C1—C3i—C2i | −178.50 (9) | C8—C9—C12—O6 | 180.00 (13) |
C2—C1—C4—O1 | −77.67 (13) | C10—C9—C12—O5 | 176.29 (10) |
C2—C1—C4—O2 | 105.48 (12) | C10—C9—C12—O6 | −2.45 (18) |
C3i—C1—C4—O1 | 100.68 (12) | C9—C10—C11—C6 | 0.85 (17) |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1i | 0.959 (19) | 1.82 (2) | 2.7570 (13) | 165.5 (15) |
N1—H1B···O1ii | 0.943 (18) | 1.821 (19) | 2.7176 (12) | 157.8 (18) |
N1—H1C···O2iii | 0.909 (19) | 1.980 (19) | 2.8633 (13) | 163.6 (17) |
O4—H4···O3iv | 0.92 (3) | 1.69 (3) | 2.6032 (14) | 174 (2) |
O5—H5···O2v | 0.94 (3) | 1.74 (3) | 2.6627 (15) | 171.3 (18) |
C7—H7···O2iii | 0.962 (16) | 2.534 (17) | 3.2343 (15) | 129.7 (12) |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x, y, z−1; (iii) −x+1, −y, −z+1; (iv) −x+2, −y+1, −z+1; (v) −x+1, −y+1, −z+1. |
bis(3-Aminopyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate tetrahydrate (comp1-293K)
top
Crystal data top
C10H4O8·2(C5H7N2)·4(H2O) | F(000) = 540 |
Mr = 514.44 | Dx = 1.456 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 6160 reflections |
a = 9.2348 (2) Å | θ = 2.8–37.8° |
b = 17.6801 (4) Å | µ = 0.12 mm−1 |
c = 7.3278 (2) Å | T = 293 K |
β = 101.340 (2)° | Prism, yellow |
V = 1173.07 (5) Å3 | 0.40 × 0.37 × 0.35 mm |
Z = 2 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 6040 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3343 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.040 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 37.9°, θmin = 3.1° |
ω scans | h = −15→13 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −29→29 |
Tmin = 0.800, Tmax = 1.000 | l = −9→12 |
23723 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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0692P)2] where P = (Fo2 + 2Fc2)/3 |
6040 reflections | (Δ/σ)max < 0.001 |
164 parameters | Δρmax = 0.40 e Å−3 |
0 restraints | Δρmin = −0.33 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
C1 | 0.56967 (10) | 0.04307 (4) | 0.15341 (10) | 0.01998 (15) | |
C2 | 0.65242 (9) | −0.00633 (4) | 0.06457 (10) | 0.02014 (15) | |
C3 | 0.41910 (10) | 0.04884 (4) | 0.08705 (11) | 0.02183 (15) | |
C4 | 0.63507 (10) | 0.08875 (4) | 0.32445 (11) | 0.02231 (16) | |
C5 | 0.81475 (10) | −0.01282 (5) | 0.13067 (12) | 0.02479 (17) | |
C6 | 0.17577 (13) | 0.11249 (6) | 0.42967 (15) | 0.0344 (2) | |
C7 | 0.12811 (13) | 0.18697 (6) | 0.41174 (17) | 0.0404 (2) | |
C8 | 0.22580 (15) | 0.24186 (6) | 0.50136 (18) | 0.0439 (3) | |
C9 | 0.36141 (14) | 0.22177 (6) | 0.60206 (16) | 0.0394 (2) | |
C10 | 0.40330 (13) | 0.14729 (6) | 0.61454 (14) | 0.0346 (2) | |
N1 | 0.30885 (10) | 0.09579 (5) | 0.52709 (11) | 0.03089 (18) | |
N2 | −0.00548 (17) | 0.20442 (9) | 0.3056 (3) | 0.0773 (5) | |
O1 | 0.66452 (9) | 0.05385 (4) | 0.47616 (9) | 0.03288 (17) | |
O2 | 0.64639 (10) | 0.15803 (4) | 0.30413 (9) | 0.03618 (18) | |
O3 | 0.88630 (9) | 0.03398 (5) | 0.22858 (13) | 0.0467 (2) | |
O4 | 0.87138 (9) | −0.07444 (4) | 0.07446 (13) | 0.0447 (2) | |
O5 | 0.69507 (13) | 0.30088 (5) | 0.45436 (14) | 0.0513 (3) | |
O6 | 0.86345 (11) | 0.38948 (7) | 0.28280 (15) | 0.0676 (4) | |
H1 | 0.3334 (18) | 0.0427 (9) | 0.5348 (19) | 0.057 (4)* | |
H2A | −0.033 (3) | 0.2517 (14) | 0.307 (3) | 0.102 (7)* | |
H2B | −0.064 (4) | 0.1680 (18) | 0.254 (4) | 0.157 (11)* | |
H3 | 0.3616 (13) | 0.0830 (6) | 0.1496 (15) | 0.026 (3)* | |
H4 | 0.976 (2) | −0.0789 (10) | 0.138 (3) | 0.086 (6)* | |
H5A | 0.693 (2) | 0.2544 (11) | 0.442 (2) | 0.071 (5)* | |
H5B | 0.675 (2) | 0.3096 (9) | 0.559 (3) | 0.070 (5)* | |
H6 | 0.1164 (17) | 0.0700 (8) | 0.3685 (19) | 0.050 (4)* | |
H6A | 0.8138 (19) | 0.3657 (9) | 0.340 (2) | 0.053 (4)* | |
H6B | 0.805 (2) | 0.4043 (10) | 0.181 (3) | 0.075 (5)* | |
H8 | 0.193 (2) | 0.2945 (10) | 0.488 (2) | 0.066 (5)* | |
H9 | 0.427 (2) | 0.2607 (9) | 0.659 (2) | 0.061 (4)* | |
H10 | 0.5013 (18) | 0.1289 (8) | 0.680 (2) | 0.053 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0191 (4) | 0.0186 (3) | 0.0204 (3) | −0.0011 (3) | −0.0006 (3) | −0.0023 (2) |
C2 | 0.0165 (4) | 0.0198 (3) | 0.0225 (3) | −0.0005 (3) | 0.0000 (3) | −0.0026 (3) |
C3 | 0.0197 (4) | 0.0220 (3) | 0.0228 (3) | 0.0012 (3) | 0.0016 (3) | −0.0052 (3) |
C4 | 0.0208 (4) | 0.0211 (3) | 0.0229 (3) | 0.0006 (3) | −0.0008 (3) | −0.0055 (3) |
C5 | 0.0187 (4) | 0.0264 (4) | 0.0280 (4) | −0.0002 (3) | 0.0014 (3) | −0.0047 (3) |
C6 | 0.0296 (5) | 0.0299 (4) | 0.0411 (5) | −0.0049 (4) | 0.0007 (4) | −0.0023 (4) |
C7 | 0.0271 (5) | 0.0351 (5) | 0.0547 (6) | 0.0015 (4) | −0.0027 (5) | 0.0004 (4) |
C8 | 0.0417 (7) | 0.0264 (5) | 0.0610 (7) | 0.0002 (4) | 0.0035 (6) | −0.0026 (4) |
C9 | 0.0345 (6) | 0.0351 (5) | 0.0467 (6) | −0.0105 (4) | 0.0032 (5) | −0.0061 (4) |
C10 | 0.0267 (5) | 0.0396 (5) | 0.0353 (5) | −0.0005 (4) | 0.0005 (4) | −0.0013 (4) |
N1 | 0.0335 (5) | 0.0272 (4) | 0.0308 (4) | 0.0020 (3) | 0.0033 (3) | 0.0005 (3) |
N2 | 0.0398 (7) | 0.0570 (8) | 0.1182 (12) | 0.0111 (6) | −0.0262 (8) | 0.0006 (8) |
O1 | 0.0426 (5) | 0.0278 (3) | 0.0239 (3) | 0.0018 (3) | −0.0041 (3) | −0.0023 (2) |
O2 | 0.0525 (5) | 0.0198 (3) | 0.0325 (3) | −0.0039 (3) | −0.0008 (3) | −0.0053 (2) |
O3 | 0.0212 (4) | 0.0473 (4) | 0.0660 (5) | −0.0022 (3) | −0.0052 (4) | −0.0283 (4) |
O4 | 0.0209 (4) | 0.0385 (4) | 0.0688 (5) | 0.0076 (3) | −0.0057 (4) | −0.0230 (4) |
O5 | 0.0762 (8) | 0.0336 (4) | 0.0494 (5) | −0.0176 (4) | 0.0252 (5) | −0.0106 (3) |
O6 | 0.0330 (5) | 0.1075 (9) | 0.0530 (5) | −0.0318 (6) | −0.0145 (4) | 0.0367 (6) |
Geometric parameters (Å, º) top
O1—C4 | 1.2537 (10) | C1—C4 | 1.5134 (11) |
O2—C4 | 1.2408 (10) | C1—C2 | 1.4022 (11) |
O3—C5 | 1.2040 (13) | C1—C3 | 1.3836 (13) |
O4—C5 | 1.3095 (12) | C2—C3i | 1.3953 (11) |
O4—H4 | 0.99 (2) | C2—C5 | 1.4864 (12) |
O5—H5B | 0.84 (2) | C3—H3 | 0.976 (11) |
O5—H5A | 0.827 (19) | C6—C7 | 1.3865 (15) |
O6—H6A | 0.799 (16) | C7—C8 | 1.3978 (17) |
O6—H6B | 0.87 (2) | C8—C9 | 1.3695 (18) |
N1—C10 | 1.3344 (14) | C9—C10 | 1.3704 (15) |
N1—C6 | 1.3275 (15) | C6—H6 | 0.985 (14) |
N2—C7 | 1.358 (2) | C8—H8 | 0.978 (18) |
N1—H1 | 0.965 (16) | C9—H9 | 0.957 (17) |
N2—H2A | 0.88 (3) | C10—H10 | 0.992 (16) |
N2—H2B | 0.88 (3) | | |
| | | |
C5—O4—H4 | 109.4 (11) | O3—C5—C2 | 122.77 (8) |
H5A—O5—H5B | 106.2 (15) | O4—C5—C2 | 113.66 (8) |
H6A—O6—H6B | 106.6 (17) | C1—C3—H3 | 118.9 (7) |
C6—N1—C10 | 123.72 (9) | C2i—C3—H3 | 119.4 (7) |
C6—N1—H1 | 115.5 (9) | N1—C6—C7 | 120.35 (10) |
C10—N1—H1 | 120.8 (9) | N2—C7—C6 | 120.38 (12) |
C7—N2—H2B | 120 (2) | N2—C7—C8 | 122.75 (12) |
C7—N2—H2A | 116.1 (17) | C6—C7—C8 | 116.83 (11) |
H2A—N2—H2B | 124 (3) | C7—C8—C9 | 120.69 (10) |
C2—C1—C3 | 118.98 (7) | C8—C9—C10 | 120.09 (11) |
C3—C1—C4 | 117.49 (7) | N1—C10—C9 | 118.32 (11) |
C2—C1—C4 | 123.49 (8) | N1—C6—H6 | 116.7 (9) |
C1—C2—C3i | 119.30 (8) | C7—C6—H6 | 122.9 (9) |
C3i—C2—C5 | 120.47 (7) | C9—C8—H8 | 122.2 (10) |
C1—C2—C5 | 120.24 (7) | C7—C8—H8 | 117.1 (10) |
C1—C3—C2i | 121.72 (7) | C8—C9—H9 | 118.8 (10) |
O1—C4—C1 | 116.96 (7) | C10—C9—H9 | 121.1 (10) |
O2—C4—C1 | 117.18 (7) | C9—C10—H10 | 124.5 (8) |
O1—C4—O2 | 125.70 (8) | N1—C10—H10 | 117.2 (8) |
O3—C5—O4 | 123.57 (9) | | |
| | | |
C10—N1—C6—C7 | 0.91 (17) | C3i—C2—C5—O3 | 161.83 (9) |
C6—N1—C10—C9 | −0.58 (16) | C1—C2—C5—O3 | −17.73 (13) |
C3—C1—C2—C5 | 178.99 (7) | C1—C2—C5—O4 | 161.39 (8) |
C4—C1—C2—C3i | 176.89 (7) | C5—C2—C3i—C1i | −178.97 (7) |
C2—C1—C3—C2i | 0.59 (11) | C3i—C2—C5—O4 | −19.05 (11) |
C4—C1—C2—C5 | −3.55 (11) | C1—C2—C3i—C1i | 0.60 (11) |
C2—C1—C4—O1 | −75.35 (11) | N1—C6—C7—C8 | −0.46 (17) |
C2—C1—C4—O2 | 108.93 (10) | N1—C6—C7—N2 | 177.20 (13) |
C4—C1—C3—C2i | −177.02 (7) | N2—C7—C8—C9 | −177.86 (15) |
C3—C1—C4—O2 | −73.57 (11) | C6—C7—C8—C9 | −0.27 (19) |
C3—C1—C2—C3i | −0.58 (11) | C7—C8—C9—C10 | 0.59 (19) |
C3—C1—C4—O1 | 102.15 (10) | C8—C9—C10—N1 | −0.18 (17) |
Symmetry code: (i) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1ii | 0.965 (16) | 1.709 (16) | 2.6576 (11) | 166.8 (15) |
N2—H2B···O3iii | 0.88 (3) | 2.41 (3) | 3.1900 (18) | 148 (3) |
O4—H4···O6iv | 0.99 (2) | 1.584 (19) | 2.5476 (14) | 163.2 (17) |
O5—H5A···O2 | 0.827 (19) | 1.984 (18) | 2.7565 (11) | 155.2 (15) |
O5—H5B···O2v | 0.84 (2) | 1.95 (2) | 2.7843 (12) | 172.1 (15) |
O6—H6A···O5 | 0.799 (16) | 1.892 (17) | 2.6872 (15) | 173.5 (15) |
O6—H6B···O1vi | 0.87 (2) | 1.93 (2) | 2.7936 (13) | 172 (2) |
C6—H6···O3iii | 0.985 (14) | 2.262 (15) | 3.1137 (15) | 144.2 (12) |
C8—H8···O4vii | 0.978 (18) | 2.414 (18) | 3.3862 (13) | 173.1 (13) |
C9—H9···O2v | 0.957 (17) | 2.540 (17) | 3.4788 (14) | 166.9 (14) |
Symmetry codes: (ii) −x+1, −y, −z+1; (iii) x−1, y, z; (iv) −x+2, y−1/2, −z+1/2; (v) x, −y+1/2, z+1/2; (vi) x, −y+1/2, z−1/2; (vii) −x+1, y+1/2, −z+1/2. |
bis(3-Carboxypyridinium) 2,5-dicarboxybenzene-1,4-dicarboxylate (comp2-293K)
top
Crystal data top
C10H4O8·2(C6H6NO2) | F(000) = 516 |
Mr = 500.37 | Dx = 1.611 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 5730 reflections |
a = 7.0774 (2) Å | θ = 2.9–29.6° |
b = 7.5332 (3) Å | µ = 0.13 mm−1 |
c = 19.4180 (6) Å | T = 293 K |
β = 94.931 (3)° | Prism, colourless |
V = 1031.45 (6) Å3 | 0.20 × 0.15 × 0.15 mm |
Z = 2 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 2439 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 1707 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 29.5°, θmin = 2.9° |
ω scans | h = −7→9 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −10→7 |
Tmin = 0.972, Tmax = 1.000 | l = −26→23 |
5414 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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.087 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0527P)2] where P = (Fo2 + 2Fc2)/3 |
2439 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.16 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
C1 | −0.14837 (15) | 0.09990 (16) | 0.52643 (6) | 0.0240 (3) | |
C2 | −0.16705 (15) | 0.04037 (16) | 0.45714 (6) | 0.0248 (3) | |
C3 | 0.01914 (16) | 0.05628 (17) | 0.56601 (6) | 0.0257 (3) | |
C4 | −0.28527 (17) | 0.20614 (17) | 0.56580 (7) | 0.0295 (3) | |
C5 | −0.33098 (16) | 0.06868 (18) | 0.40170 (7) | 0.0308 (3) | |
C6 | 0.17723 (18) | 0.48601 (18) | 0.60245 (7) | 0.0327 (3) | |
C7 | 0.06375 (16) | 0.57409 (17) | 0.64481 (6) | 0.0283 (3) | |
C8 | 0.12782 (19) | 0.6000 (2) | 0.71352 (7) | 0.0358 (3) | |
C9 | 0.3063 (2) | 0.5384 (2) | 0.73746 (7) | 0.0396 (4) | |
C10 | 0.41443 (19) | 0.4525 (2) | 0.69327 (8) | 0.0390 (3) | |
C11 | −0.12333 (18) | 0.64013 (18) | 0.61342 (6) | 0.0307 (3) | |
N1 | 0.34812 (16) | 0.42766 (16) | 0.62750 (6) | 0.0366 (3) | |
O1 | −0.24413 (14) | 0.24546 (13) | 0.62601 (5) | 0.0401 (3) | |
O2 | −0.44612 (13) | 0.25480 (14) | 0.53440 (5) | 0.0446 (3) | |
O3 | −0.32381 (14) | 0.00197 (16) | 0.34530 (5) | 0.0531 (3) | |
O4 | −0.47219 (13) | 0.16619 (14) | 0.41630 (5) | 0.0447 (3) | |
O5 | −0.22275 (14) | 0.72144 (15) | 0.65787 (5) | 0.0461 (3) | |
O6 | −0.17292 (13) | 0.62207 (14) | 0.55295 (5) | 0.0444 (3) | |
H1 | 0.424 (3) | 0.368 (2) | 0.5940 (9) | 0.061 (5)* | |
H3 | 0.0282 (18) | 0.0980 (17) | 0.6131 (7) | 0.027 (3)* | |
H4 | −0.463 (3) | 0.213 (2) | 0.4755 (10) | 0.077 (6)* | |
H5 | −0.332 (3) | 0.759 (3) | 0.6333 (11) | 0.085 (6)* | |
H6 | 0.140 (2) | 0.4656 (19) | 0.5544 (8) | 0.041 (4)* | |
H8 | 0.051 (2) | 0.6631 (19) | 0.7421 (7) | 0.038 (4)* | |
H9 | 0.354 (2) | 0.556 (2) | 0.7856 (8) | 0.045 (4)* | |
H10 | 0.546 (2) | 0.4051 (19) | 0.7036 (8) | 0.044 (4)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0184 (5) | 0.0266 (6) | 0.0270 (6) | 0.0010 (5) | 0.0021 (4) | 0.0034 (5) |
C2 | 0.0188 (5) | 0.0274 (6) | 0.0275 (6) | 0.0001 (5) | −0.0015 (5) | 0.0031 (5) |
C3 | 0.0227 (6) | 0.0300 (7) | 0.0239 (6) | 0.0006 (5) | −0.0003 (4) | −0.0006 (5) |
C4 | 0.0234 (6) | 0.0320 (7) | 0.0332 (7) | 0.0046 (6) | 0.0035 (5) | 0.0028 (6) |
C5 | 0.0222 (6) | 0.0375 (7) | 0.0316 (7) | 0.0023 (6) | −0.0050 (5) | 0.0023 (6) |
C6 | 0.0322 (7) | 0.0355 (7) | 0.0301 (7) | 0.0037 (6) | 0.0002 (5) | −0.0032 (6) |
C7 | 0.0264 (6) | 0.0317 (7) | 0.0263 (6) | 0.0023 (6) | 0.0000 (5) | −0.0011 (5) |
C8 | 0.0346 (7) | 0.0448 (8) | 0.0274 (7) | 0.0100 (7) | −0.0004 (6) | −0.0041 (6) |
C9 | 0.0365 (7) | 0.0473 (9) | 0.0332 (7) | 0.0082 (7) | −0.0078 (6) | −0.0019 (7) |
C10 | 0.0289 (7) | 0.0396 (8) | 0.0471 (8) | 0.0074 (7) | −0.0040 (6) | 0.0013 (7) |
C11 | 0.0272 (6) | 0.0348 (7) | 0.0295 (7) | 0.0029 (6) | −0.0010 (5) | 0.0000 (6) |
N1 | 0.0313 (6) | 0.0384 (7) | 0.0408 (7) | 0.0085 (5) | 0.0066 (5) | −0.0043 (5) |
O1 | 0.0376 (5) | 0.0537 (6) | 0.0293 (5) | 0.0129 (5) | 0.0056 (4) | −0.0049 (4) |
O2 | 0.0277 (5) | 0.0635 (7) | 0.0416 (6) | 0.0215 (5) | −0.0019 (4) | −0.0088 (5) |
O3 | 0.0380 (5) | 0.0832 (9) | 0.0351 (6) | 0.0191 (6) | −0.0142 (4) | −0.0149 (5) |
O4 | 0.0299 (5) | 0.0616 (7) | 0.0404 (6) | 0.0218 (5) | −0.0104 (4) | −0.0054 (5) |
O5 | 0.0326 (5) | 0.0694 (7) | 0.0352 (5) | 0.0215 (5) | −0.0031 (4) | −0.0056 (5) |
O6 | 0.0414 (5) | 0.0594 (7) | 0.0303 (5) | 0.0109 (5) | −0.0092 (4) | −0.0033 (4) |
Geometric parameters (Å, º) top
O3—C5 | 1.2100 (17) | C2—C5 | 1.5283 (17) |
O4—C5 | 1.2913 (16) | C1—C4 | 1.5136 (17) |
O1—C4 | 1.2169 (17) | C1—C3 | 1.3955 (16) |
O2—C4 | 1.2972 (16) | C3—H3 | 0.964 (14) |
O4—H4 | 1.199 (19) | C6—C7 | 1.3695 (18) |
O2—H4 | 1.182 (19) | C7—C8 | 1.3856 (18) |
O5—C11 | 1.3114 (16) | C7—C11 | 1.4945 (17) |
O6—C11 | 1.2040 (15) | C8—C9 | 1.388 (2) |
O5—H5 | 0.92 (2) | C9—C10 | 1.362 (2) |
N1—C10 | 1.3354 (19) | C6—H6 | 0.958 (15) |
N1—C6 | 1.3385 (17) | C8—H8 | 0.939 (15) |
N1—H1 | 0.987 (19) | C9—H9 | 0.977 (15) |
C2—C3i | 1.3816 (16) | C10—H10 | 1.001 (14) |
C2—C1 | 1.4136 (16) | | |
| | | |
C5—O4—H4 | 113.5 (10) | C2i—C3—H3 | 119.3 (8) |
C4—O2—H4 | 113.0 (10) | N1—C6—C7 | 119.94 (12) |
C11—O5—H5 | 106.1 (14) | C6—C7—C8 | 119.10 (12) |
C6—N1—C10 | 122.27 (12) | C6—C7—C11 | 117.46 (11) |
C6—N1—H1 | 115.9 (11) | C8—C7—C11 | 123.44 (11) |
C10—N1—H1 | 121.9 (11) | C7—C8—C9 | 119.25 (12) |
C3i—C2—C5 | 113.26 (10) | C8—C9—C10 | 119.51 (13) |
C1—C2—C5 | 129.01 (10) | N1—C10—C9 | 119.93 (13) |
C1—C2—C3i | 117.73 (10) | O5—C11—O6 | 124.53 (12) |
C2—C1—C3 | 117.07 (10) | O5—C11—C7 | 113.19 (10) |
C2—C1—C4 | 129.56 (10) | O6—C11—C7 | 122.27 (11) |
C3—C1—C4 | 113.37 (10) | N1—C6—H6 | 117.7 (9) |
C2—C3i—C1i | 125.20 (11) | C7—C6—H6 | 122.3 (9) |
O4—C5—C2 | 118.67 (11) | C7—C8—H8 | 118.8 (9) |
O3—C5—O4 | 121.90 (12) | C9—C8—H8 | 121.9 (9) |
O3—C5—C2 | 119.42 (11) | C8—C9—H9 | 120.4 (9) |
O1—C4—C1 | 120.22 (11) | C10—C9—H9 | 120.1 (9) |
O1—C4—O2 | 120.71 (12) | N1—C10—H10 | 112.7 (9) |
O2—C4—C1 | 119.08 (11) | C9—C10—H10 | 127.4 (9) |
C1—C3—H3 | 115.5 (8) | | |
| | | |
C10—N1—C6—C7 | −0.2 (2) | C2—C1—C3—C2i | −0.15 (19) |
C6—N1—C10—C9 | 0.6 (2) | C4—C1—C3—C2i | 179.69 (12) |
C3i—C2—C1—C4 | −179.68 (12) | C3—C1—C4—O2 | 179.91 (12) |
C5—C2—C1—C3 | −179.32 (12) | C3—C1—C4—O1 | 0.12 (18) |
C1—C2—C3i—C1i | −0.15 (19) | N1—C6—C7—C11 | 178.45 (12) |
C5—C2—C1—C4 | 0.9 (2) | N1—C6—C7—C8 | −0.6 (2) |
C1—C2—C5—O3 | −177.64 (13) | C6—C7—C8—C9 | 0.9 (2) |
C1—C2—C5—O4 | 3.5 (2) | C6—C7—C11—O5 | 179.51 (12) |
C3i—C2—C5—O3 | 2.88 (18) | C6—C7—C11—O6 | −1.9 (2) |
C3i—C2—C5—O4 | −175.96 (12) | C8—C7—C11—O5 | −1.53 (19) |
C3i—C2—C1—C3 | 0.14 (17) | C8—C7—C11—O6 | 177.05 (13) |
C5—C2—C3i—C1i | 179.39 (12) | C11—C7—C8—C9 | −178.03 (13) |
C2—C1—C4—O2 | −0.3 (2) | C7—C8—C9—C10 | −0.5 (2) |
C2—C1—C4—O1 | 179.94 (14) | C8—C9—C10—N1 | −0.2 (2) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2ii | 0.987 (19) | 1.759 (18) | 2.7454 (15) | 177.9 (17) |
O2—H4···O4 | 1.182 (19) | 1.199 (19) | 2.3803 (14) | 177 (2) |
O5—H5···O4iii | 0.92 (2) | 1.71 (2) | 2.6302 (14) | 177 (2) |
C6—H6···O6iv | 0.958 (15) | 2.220 (15) | 3.1231 (17) | 156.8 (12) |
C9—H9···O3v | 0.977 (15) | 2.505 (15) | 3.2231 (17) | 130.2 (11) |
C9—H9···O1vi | 0.977 (15) | 2.410 (15) | 3.1394 (17) | 131.0 (11) |
C10—H10···O1ii | 1.001 (14) | 2.511 (15) | 3.2435 (17) | 129.7 (11) |
Symmetry codes: (ii) x+1, y, z; (iii) −x−1, −y+1, −z+1; (iv) −x, −y+1, −z+1; (v) x+1, −y+1/2, z+1/2; (vi) −x, y+1/2, −z+3/2. |
bis(3-Carboxyphenylammonium) 2,5-dicarboxybenzene-1,4-dicarboxylate dihydrate (comp3-293K)
top
Crystal data top
C10H4O8·2(C7H8NO2)·2(H2O) | Z = 1 |
Mr = 564.45 | F(000) = 294 |
Triclinic, P1 | Dx = 1.594 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 7.4644 (3) Å | Cell parameters from 7082 reflections |
b = 7.7371 (3) Å | θ = 3.4–29.5° |
c = 10.3355 (4) Å | µ = 0.13 mm−1 |
α = 80.204 (3)° | T = 293 K |
β = 89.508 (3)° | Prism, colourless |
γ = 87.937 (3)° | 0.99 × 0.49 × 0.34 mm |
V = 587.82 (4) Å3 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 3019 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 2551 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 29.6°, θmin = 2.7° |
ω scans | h = −9→10 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −10→10 |
Tmin = 0.925, Tmax = 1.000 | l = −14→14 |
14512 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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.121 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0706P)2 + 0.1136P] where P = (Fo2 + 2Fc2)/3 |
3019 reflections | (Δ/σ)max < 0.001 |
229 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.30 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
O1 | 0.10335 (14) | 0.56814 (13) | 0.32770 (9) | 0.0381 (3) | |
O2 | −0.04612 (15) | 0.81119 (12) | 0.24702 (9) | 0.0400 (3) | |
O3 | −0.24713 (14) | 0.89424 (12) | −0.14801 (9) | 0.0387 (3) | |
O4 | −0.19588 (15) | 0.94445 (13) | 0.05005 (10) | 0.0442 (3) | |
O5 | 0.40642 (15) | 0.79649 (13) | 0.16504 (10) | 0.0415 (3) | |
O6 | 0.50306 (15) | 0.81309 (13) | 0.36634 (10) | 0.0410 (3) | |
O7 | 0.75957 (16) | 0.87591 (14) | 0.56732 (13) | 0.0466 (3) | |
N1 | 0.87508 (16) | 0.23248 (15) | 0.48328 (11) | 0.0321 (3) | |
C1 | 0.00387 (15) | 0.59054 (14) | 0.10818 (11) | 0.0225 (2) | |
C2 | −0.08363 (15) | 0.66963 (14) | −0.00843 (11) | 0.0224 (2) | |
C3 | 0.08382 (16) | 0.42444 (15) | 0.11184 (11) | 0.0240 (2) | |
C4 | 0.02215 (16) | 0.66117 (16) | 0.23582 (11) | 0.0266 (3) | |
C5 | −0.18127 (16) | 0.84748 (15) | −0.03776 (12) | 0.0272 (3) | |
C6 | 0.75658 (16) | 0.31303 (15) | 0.37650 (11) | 0.0254 (2) | |
C7 | 0.67931 (16) | 0.47663 (15) | 0.37960 (11) | 0.0258 (3) | |
C8 | 0.57036 (16) | 0.55387 (15) | 0.27569 (11) | 0.0255 (2) | |
C9 | 0.53897 (17) | 0.46379 (17) | 0.17272 (12) | 0.0309 (3) | |
C10 | 0.61699 (19) | 0.29875 (18) | 0.17197 (13) | 0.0335 (3) | |
C11 | 0.72757 (18) | 0.22265 (16) | 0.27435 (12) | 0.0307 (3) | |
C12 | 0.49079 (17) | 0.73396 (16) | 0.27491 (12) | 0.0290 (3) | |
H1A | 0.838 (3) | 0.120 (3) | 0.5232 (19) | 0.052 (5)* | |
H1B | 0.993 (3) | 0.221 (2) | 0.4546 (18) | 0.048 (5)* | |
H1C | 0.884 (3) | 0.305 (3) | 0.555 (2) | 0.061 (6)* | |
H3 | 0.138 (2) | 0.372 (2) | 0.1894 (16) | 0.034 (4)* | |
H4 | −0.129 (4) | 0.877 (4) | 0.148 (3) | 0.101 (9)* | |
H5 | 0.354 (3) | 0.904 (3) | 0.166 (2) | 0.077 (7)* | |
H7 | 0.706 (2) | 0.538 (2) | 0.4541 (16) | 0.037 (4)* | |
H7A | 0.668 (5) | 0.851 (4) | 0.510 (3) | 0.125 (11)* | |
H7B | 0.731 (5) | 0.874 (4) | 0.646 (4) | 0.129 (12)* | |
H9 | 0.459 (2) | 0.517 (2) | 0.1053 (17) | 0.044 (4)* | |
H10 | 0.597 (2) | 0.238 (2) | 0.0990 (17) | 0.045 (4)* | |
H11 | 0.783 (3) | 0.107 (3) | 0.2755 (18) | 0.052 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0532 (6) | 0.0357 (5) | 0.0267 (5) | 0.0122 (4) | −0.0138 (4) | −0.0115 (4) |
O2 | 0.0622 (7) | 0.0295 (5) | 0.0310 (5) | 0.0145 (4) | −0.0105 (4) | −0.0155 (4) |
O3 | 0.0540 (6) | 0.0269 (5) | 0.0343 (5) | 0.0156 (4) | −0.0159 (4) | −0.0050 (4) |
O4 | 0.0652 (7) | 0.0301 (5) | 0.0388 (6) | 0.0234 (5) | −0.0135 (5) | −0.0148 (4) |
O5 | 0.0576 (6) | 0.0305 (5) | 0.0348 (5) | 0.0192 (4) | −0.0139 (4) | −0.0043 (4) |
O6 | 0.0539 (6) | 0.0339 (5) | 0.0369 (5) | 0.0153 (4) | −0.0084 (4) | −0.0135 (4) |
O7 | 0.0551 (7) | 0.0401 (6) | 0.0444 (6) | 0.0107 (5) | 0.0010 (5) | −0.0091 (5) |
N1 | 0.0404 (6) | 0.0289 (6) | 0.0272 (5) | 0.0128 (5) | −0.0118 (5) | −0.0081 (4) |
C1 | 0.0265 (5) | 0.0209 (5) | 0.0210 (5) | 0.0016 (4) | −0.0023 (4) | −0.0062 (4) |
C2 | 0.0252 (5) | 0.0183 (5) | 0.0238 (5) | 0.0030 (4) | −0.0030 (4) | −0.0042 (4) |
C3 | 0.0290 (6) | 0.0215 (5) | 0.0212 (5) | 0.0039 (4) | −0.0049 (4) | −0.0038 (4) |
C4 | 0.0317 (6) | 0.0264 (6) | 0.0231 (5) | 0.0009 (4) | −0.0029 (4) | −0.0085 (4) |
C5 | 0.0307 (6) | 0.0207 (5) | 0.0302 (6) | 0.0056 (4) | −0.0041 (5) | −0.0051 (4) |
C6 | 0.0301 (6) | 0.0239 (5) | 0.0219 (5) | 0.0050 (4) | −0.0051 (4) | −0.0044 (4) |
C7 | 0.0313 (6) | 0.0244 (5) | 0.0223 (5) | 0.0042 (4) | −0.0031 (4) | −0.0068 (4) |
C8 | 0.0279 (6) | 0.0236 (5) | 0.0245 (6) | 0.0050 (4) | −0.0016 (4) | −0.0035 (4) |
C9 | 0.0342 (6) | 0.0331 (6) | 0.0251 (6) | 0.0058 (5) | −0.0078 (5) | −0.0057 (5) |
C10 | 0.0414 (7) | 0.0328 (6) | 0.0291 (6) | 0.0033 (5) | −0.0087 (5) | −0.0135 (5) |
C11 | 0.0400 (7) | 0.0234 (6) | 0.0299 (6) | 0.0066 (5) | −0.0051 (5) | −0.0094 (5) |
C12 | 0.0313 (6) | 0.0262 (6) | 0.0286 (6) | 0.0060 (5) | −0.0010 (5) | −0.0032 (4) |
Geometric parameters (Å, º) top
O1—C4 | 1.2382 (15) | N1—H1A | 0.94 (2) |
O2—C4 | 1.2738 (16) | N1—H1B | 0.93 (2) |
O3—C5 | 1.2359 (15) | N1—H1C | 1.01 (2) |
O4—C5 | 1.2738 (16) | C6—C7 | 1.3773 (17) |
O2—H4 | 1.23 (3) | C6—C11 | 1.3844 (17) |
O4—H4 | 1.17 (3) | C7—C8 | 1.3905 (16) |
C1—C3 | 1.3920 (16) | C8—C12 | 1.4937 (17) |
C1—C2 | 1.4098 (16) | C8—C9 | 1.3935 (17) |
C1—C4 | 1.5203 (16) | C9—C10 | 1.3855 (19) |
C2—C3i | 1.3917 (16) | C10—C11 | 1.3841 (19) |
C2—C5 | 1.5186 (16) | C7—H7 | 0.996 (16) |
O5—C12 | 1.3129 (16) | O7—H7A | 0.95 (3) |
O6—C12 | 1.2160 (16) | O7—H7B | 0.84 (4) |
N1—C6 | 1.4601 (16) | C9—H9 | 0.950 (16) |
C3—H3 | 0.924 (16) | C10—H10 | 0.969 (17) |
O5—H5 | 0.91 (2) | C11—H11 | 0.97 (2) |
| | | |
C4—O2—H4 | 111.2 (15) | C6—N1—H1A | 112.3 (13) |
C5—O4—H4 | 111.3 (15) | N1—C6—C7 | 119.21 (10) |
C2—C1—C4 | 128.63 (10) | N1—C6—C11 | 118.61 (11) |
C3—C1—C4 | 113.49 (10) | C7—C6—C11 | 122.18 (11) |
C2—C1—C3 | 117.87 (10) | C6—C7—C8 | 118.67 (11) |
C3i—C2—C5 | 114.11 (10) | C7—C8—C12 | 119.44 (10) |
C1—C2—C5 | 128.42 (10) | C7—C8—C9 | 119.74 (11) |
C1—C2—C3i | 117.46 (10) | C9—C8—C12 | 120.81 (11) |
C1—C3—C2i | 124.67 (11) | C8—C9—C10 | 120.67 (12) |
O1—C4—C1 | 118.05 (11) | C9—C10—C11 | 119.70 (12) |
O2—C4—C1 | 120.36 (10) | C6—C11—C10 | 119.03 (12) |
O1—C4—O2 | 121.59 (11) | O5—C12—O6 | 124.03 (12) |
O4—C5—C2 | 120.44 (11) | O5—C12—C8 | 112.53 (10) |
O3—C5—O4 | 121.23 (11) | O6—C12—C8 | 123.44 (11) |
O3—C5—C2 | 118.33 (11) | C6—C7—H7 | 119.5 (9) |
C1—C3—H3 | 117.4 (10) | C8—C7—H7 | 121.8 (9) |
C2i—C3—H3 | 117.9 (10) | H7A—O7—H7B | 117 (3) |
C12—O5—H5 | 112.5 (13) | C10—C9—H9 | 121.3 (10) |
C6—N1—H1C | 112.8 (13) | C8—C9—H9 | 118.0 (10) |
H1A—N1—H1B | 108.3 (17) | C9—C10—H10 | 120.3 (10) |
C6—N1—H1B | 111.8 (11) | C11—C10—H10 | 120.0 (10) |
H1B—N1—H1C | 104.0 (17) | C6—C11—H11 | 120.2 (12) |
H1A—N1—H1C | 107.2 (17) | C10—C11—H11 | 120.8 (11) |
| | | |
C3—C1—C2—C5 | 179.66 (11) | C5—C2—C3i—C1i | −179.71 (11) |
C3—C1—C2—C3i | 0.03 (16) | N1—C6—C7—C8 | 178.38 (11) |
C4—C1—C2—C5 | 0.7 (2) | C11—C6—C7—C8 | −0.77 (18) |
C4—C1—C2—C3i | −178.94 (11) | N1—C6—C11—C10 | −179.31 (12) |
C2—C1—C3—C2i | −0.02 (18) | C7—C6—C11—C10 | −0.15 (19) |
C4—C1—C3—C2i | 179.09 (11) | C6—C7—C8—C9 | 1.23 (18) |
C2—C1—C4—O1 | 179.03 (12) | C6—C7—C8—C12 | −177.78 (11) |
C2—C1—C4—O2 | −0.34 (19) | C7—C8—C9—C10 | −0.79 (19) |
C3—C1—C4—O1 | 0.02 (16) | C12—C8—C9—C10 | 178.20 (12) |
C3—C1—C4—O2 | −179.35 (11) | C7—C8—C12—O5 | 173.56 (11) |
C1—C2—C5—O3 | 178.83 (12) | C7—C8—C12—O6 | −6.54 (19) |
C1—C2—C5—O4 | −1.87 (19) | C9—C8—C12—O5 | −5.43 (17) |
C3i—C2—C5—O3 | −1.53 (16) | C9—C8—C12—O6 | 174.47 (13) |
C3i—C2—C5—O4 | 177.78 (11) | C8—C9—C10—C11 | −0.2 (2) |
C1—C2—C3i—C1i | −0.03 (18) | C9—C10—C11—C6 | 0.6 (2) |
Symmetry code: (i) −x, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O7ii | 0.94 (2) | 1.98 (2) | 2.9072 (16) | 167.4 (18) |
N1—H1B···O7iii | 0.93 (2) | 1.99 (2) | 2.8938 (17) | 161.7 (15) |
N1—H1C···O1iv | 1.01 (2) | 1.68 (2) | 2.6965 (15) | 179 (3) |
O2—H4···O4 | 1.23 (3) | 1.17 (3) | 2.3873 (14) | 175 (3) |
O5—H5···O3v | 0.91 (2) | 1.71 (2) | 2.6126 (14) | 173 (2) |
O7—H7A···O6 | 0.95 (3) | 2.00 (3) | 2.9489 (16) | 171 (3) |
O7—H7B···O3vi | 0.84 (4) | 2.17 (4) | 2.9695 (16) | 160 (4) |
Symmetry codes: (ii) x, y−1, z; (iii) −x+2, −y+1, −z+1; (iv) −x+1, −y+1, −z+1; (v) −x, −y+2, −z; (vi) x+1, y, z+1. |
bis(4-Carboxyphenylammonium) 2,5-dicarboxybenzene-1,4-dicarboxylate (comp4-293K)
top
Crystal data top
C10H4O8·2(C7H8NO2) | Z = 1 |
Mr = 528.42 | F(000) = 274 |
Triclinic, P1 | Dx = 1.552 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.7107 Å |
a = 6.6314 (2) Å | Cell parameters from 11424 reflections |
b = 9.5284 (3) Å | θ = 3.1–32.7° |
c = 9.8203 (3) Å | µ = 0.13 mm−1 |
α = 66.511 (3)° | T = 293 K |
β = 87.534 (2)° | Prism, colourless |
γ = 83.336 (2)° | 0.40 × 0.35 × 0.33 mm |
V = 565.25 (3) Å3 | |
Data collection top
Xcalibur, Atlas, Gemini ultra diffractometer | 3895 independent reflections |
Radiation source: Enhance (Mo) X-ray Source | 3299 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 10.4186 pixels mm-1 | θmax = 32.8°, θmin = 3.1° |
ω scans | h = −10→9 |
Absorption correction: multi-scan CrysAlisPro, Rigaku Oxford Diffraction,
Version 1.171.39.46
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm. | k = −14→14 |
Tmin = 0.939, Tmax = 1.000 | l = −14→14 |
15972 measured reflections | |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.134 | w = 1/[σ2(Fo2) + (0.0817P)2 + 0.0909P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
3895 reflections | Δρmax = 0.40 e Å−3 |
213 parameters | Δρmin = −0.42 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.077 (11) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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 | |
C1 | −0.11784 (12) | 0.54139 (9) | 0.60340 (9) | 0.01940 (16) | |
C2 | 0.00702 (13) | 0.64408 (8) | 0.50316 (9) | 0.02011 (17) | |
C3 | 0.12325 (13) | 0.60219 (9) | 0.40074 (9) | 0.02181 (17) | |
C4 | −0.24353 (13) | 0.57707 (9) | 0.72043 (9) | 0.02236 (18) | |
C5 | 0.00844 (14) | 0.80091 (9) | 0.50067 (10) | 0.02500 (19) | |
C6 | 0.32518 (15) | 0.03038 (12) | 0.83708 (13) | 0.0325 (2) | |
C7 | 0.23788 (17) | 0.03751 (13) | 0.96639 (14) | 0.0369 (2) | |
C8 | 0.21354 (16) | 0.17564 (13) | 0.98466 (12) | 0.0342 (2) | |
C9 | 0.27948 (14) | 0.30539 (11) | 0.87323 (11) | 0.02611 (19) | |
C10 | 0.36600 (15) | 0.30052 (12) | 0.74386 (11) | 0.0292 (2) | |
C11 | 0.38898 (16) | 0.16226 (13) | 0.72606 (12) | 0.0321 (2) | |
C12 | 0.35523 (17) | −0.12104 (14) | 0.82303 (16) | 0.0405 (3) | |
H1B | 0.247 (2) | 0.437 (2) | 0.991 (2) | 0.048 (4)* | |
H1C | 0.348 (3) | 0.512 (2) | 0.8367 (19) | 0.052 (5)* | |
H1A | 0.129 (2) | 0.5011 (18) | 0.8526 (17) | 0.041 (4)* | |
H3 | 0.205 (2) | 0.6718 (16) | 0.3301 (15) | 0.028 (3)* | |
H4 | 0.122 (5) | 0.988 (4) | 0.415 (4) | 0.139 (11)* | |
H5 | 0.477 (3) | −0.210 (3) | 0.702 (2) | 0.082 (7)* | |
H7 | 0.200 (2) | −0.061 (2) | 1.0434 (19) | 0.048 (4)* | |
H8 | 0.145 (2) | 0.184 (2) | 1.0754 (18) | 0.048 (4)* | |
H10 | 0.407 (2) | 0.3946 (17) | 0.6669 (16) | 0.035 (4)* | |
H11 | 0.450 (3) | 0.161 (2) | 0.6331 (19) | 0.049 (4)* | |
N1 | 0.25418 (14) | 0.45172 (10) | 0.88989 (10) | 0.02899 (18) | |
O1 | −0.15057 (12) | 0.56443 (10) | 0.83342 (8) | 0.03569 (19) | |
O2 | −0.43055 (11) | 0.61008 (9) | 0.69765 (9) | 0.03339 (18) | |
O3 | −0.11179 (15) | 0.84899 (9) | 0.57280 (11) | 0.0479 (3) | |
O4 | 0.14384 (16) | 0.88102 (10) | 0.41386 (12) | 0.0536 (3) | |
O5 | 0.4552 (2) | −0.11283 (12) | 0.70126 (13) | 0.0597 (3) | |
O6 | 0.3003 (2) | −0.23865 (13) | 0.91400 (17) | 0.0721 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0245 (4) | 0.0163 (3) | 0.0215 (3) | −0.0027 (3) | 0.0056 (3) | −0.0121 (3) |
C2 | 0.0260 (4) | 0.0141 (3) | 0.0247 (4) | −0.0039 (3) | 0.0063 (3) | −0.0125 (3) |
C3 | 0.0285 (4) | 0.0155 (3) | 0.0256 (4) | −0.0055 (3) | 0.0097 (3) | −0.0127 (3) |
C4 | 0.0292 (4) | 0.0161 (3) | 0.0258 (4) | −0.0046 (3) | 0.0103 (3) | −0.0130 (3) |
C5 | 0.0324 (4) | 0.0167 (3) | 0.0316 (4) | −0.0067 (3) | 0.0105 (3) | −0.0155 (3) |
C6 | 0.0257 (4) | 0.0321 (5) | 0.0467 (6) | 0.0004 (3) | 0.0017 (4) | −0.0241 (4) |
C7 | 0.0351 (5) | 0.0331 (5) | 0.0453 (6) | −0.0070 (4) | 0.0102 (4) | −0.0186 (4) |
C8 | 0.0345 (5) | 0.0364 (5) | 0.0365 (5) | −0.0064 (4) | 0.0113 (4) | −0.0200 (4) |
C9 | 0.0237 (4) | 0.0303 (4) | 0.0302 (4) | −0.0008 (3) | 0.0021 (3) | −0.0190 (3) |
C10 | 0.0307 (4) | 0.0319 (4) | 0.0295 (4) | −0.0005 (3) | 0.0042 (3) | −0.0180 (4) |
C11 | 0.0316 (5) | 0.0353 (5) | 0.0366 (5) | 0.0016 (4) | 0.0037 (4) | −0.0236 (4) |
C12 | 0.0331 (5) | 0.0347 (5) | 0.0627 (7) | −0.0005 (4) | 0.0030 (5) | −0.0299 (5) |
N1 | 0.0315 (4) | 0.0324 (4) | 0.0304 (4) | −0.0030 (3) | 0.0052 (3) | −0.0208 (3) |
O1 | 0.0411 (4) | 0.0446 (4) | 0.0280 (4) | 0.0024 (3) | 0.0049 (3) | −0.0236 (3) |
O2 | 0.0281 (3) | 0.0331 (4) | 0.0484 (4) | −0.0031 (3) | 0.0103 (3) | −0.0271 (3) |
O3 | 0.0636 (5) | 0.0254 (4) | 0.0686 (6) | −0.0195 (4) | 0.0420 (5) | −0.0334 (4) |
O4 | 0.0671 (6) | 0.0301 (4) | 0.0807 (7) | −0.0289 (4) | 0.0503 (5) | −0.0384 (4) |
O5 | 0.0845 (8) | 0.0355 (5) | 0.0647 (7) | 0.0056 (5) | 0.0182 (6) | −0.0308 (5) |
O6 | 0.0849 (8) | 0.0434 (6) | 0.1023 (10) | −0.0265 (6) | 0.0421 (7) | −0.0429 (6) |
Geometric parameters (Å, º) top
O1—C4 | 1.2493 (11) | C2—C5 | 1.4859 (13) |
O2—C4 | 1.2507 (11) | C2—C3 | 1.3953 (12) |
O3—C5 | 1.2135 (13) | C3—H3 | 0.948 (14) |
O4—C5 | 1.3000 (14) | C6—C7 | 1.3960 (17) |
O4—H4 | 1.02 (4) | C6—C11 | 1.3922 (17) |
O5—C12 | 1.3209 (18) | C6—C12 | 1.4933 (19) |
O6—C12 | 1.206 (2) | C7—C8 | 1.3882 (19) |
O5—H5 | 0.92 (3) | C8—C9 | 1.3867 (16) |
N1—C9 | 1.4575 (15) | C9—C10 | 1.3869 (14) |
N1—H1C | 0.90 (2) | C10—C11 | 1.3871 (18) |
N1—H1B | 0.946 (18) | C7—H7 | 0.994 (18) |
N1—H1A | 0.918 (14) | C8—H8 | 1.010 (17) |
C1—C2 | 1.4008 (12) | C10—H10 | 0.973 (15) |
C1—C3i | 1.3894 (13) | C11—H11 | 0.987 (18) |
C1—C4 | 1.5147 (12) | | |
| | | |
C5—O4—H4 | 107.4 (19) | C2—C3—H3 | 121.1 (10) |
C12—O5—H5 | 108.2 (12) | C7—C6—C11 | 119.89 (12) |
C9—N1—H1A | 108.1 (11) | C7—C6—C12 | 118.97 (11) |
H1B—N1—H1C | 114.8 (16) | C11—C6—C12 | 121.11 (11) |
H1C—N1—H1A | 107.7 (16) | C6—C7—C8 | 120.34 (11) |
C9—N1—H1B | 111.5 (12) | C7—C8—C9 | 118.86 (10) |
H1B—N1—H1A | 103.8 (13) | N1—C9—C8 | 119.71 (9) |
C9—N1—H1C | 110.5 (13) | N1—C9—C10 | 118.71 (9) |
C3—C1i—C4i | 117.86 (7) | C8—C9—C10 | 121.57 (11) |
C2—C1—C3i | 118.98 (8) | C9—C10—C11 | 119.24 (10) |
C2—C1—C4 | 123.13 (8) | C6—C11—C10 | 120.09 (10) |
C3—C2—C5 | 119.72 (8) | O5—C12—O6 | 123.54 (15) |
C1—C2—C5 | 120.03 (8) | O5—C12—C6 | 112.17 (12) |
C1—C2—C3 | 120.19 (8) | O6—C12—C6 | 124.26 (13) |
C1—C3i—C2i | 120.84 (8) | C6—C7—H7 | 116.3 (11) |
O1—C4—C1 | 116.43 (8) | C8—C7—H7 | 123.3 (11) |
O2—C4—C1 | 117.16 (8) | C7—C8—H8 | 121.4 (11) |
O1—C4—O2 | 126.35 (9) | C9—C8—H8 | 119.7 (11) |
O3—C5—C2 | 121.44 (9) | C9—C10—H10 | 119.2 (10) |
O4—C5—C2 | 114.79 (9) | C11—C10—H10 | 121.5 (10) |
O3—C5—O4 | 123.75 (10) | C6—C11—H11 | 121.7 (12) |
C1—C3i—H3i | 118.1 (10) | C10—C11—H11 | 118.2 (12) |
| | | |
C3i—C1—C2—C5 | 177.21 (8) | C5—C2—C3—C1i | −177.23 (8) |
C3—C1—C2—C3i | −0.20 (12) | C11—C6—C7—C8 | 0.27 (16) |
C4—C1—C2—C5 | −4.78 (12) | C12—C6—C7—C8 | 178.06 (10) |
C4—C1—C2—C3 | 178.21 (8) | C7—C6—C11—C10 | 0.03 (15) |
C2—C1—C3i—C2i | −0.20 (12) | C12—C6—C11—C10 | −177.71 (10) |
C4—C1—C3i—C2i | −178.31 (8) | C7—C6—C12—O5 | −174.39 (11) |
C2—C1—C4—O1 | −77.77 (11) | C7—C6—C12—O6 | 3.53 (19) |
C2—C1—C4—O2 | 105.03 (10) | C11—C6—C12—O5 | 3.38 (16) |
C3i—C1—C4—O1 | 100.25 (10) | C11—C6—C12—O6 | −178.71 (13) |
C3i—C1—C4—O2 | −76.94 (11) | C6—C7—C8—C9 | −0.74 (16) |
C1—C2—C5—O3 | −7.82 (14) | C7—C8—C9—N1 | 179.63 (10) |
C1—C2—C5—O4 | 173.59 (9) | C7—C8—C9—C10 | 0.93 (16) |
C3—C2—C5—O3 | 169.21 (9) | N1—C9—C10—C11 | −179.35 (9) |
C3—C2—C5—O4 | −9.38 (13) | C8—C9—C10—C11 | −0.64 (15) |
C1—C2—C3—C1i | −0.20 (13) | C9—C10—C11—C6 | 0.14 (16) |
Symmetry code: (i) −x, −y+1, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1B···O1ii | 0.946 (18) | 1.809 (18) | 2.7220 (12) | 161.5 (13) |
N1—H1C···O2iii | 0.90 (2) | 2.007 (19) | 2.8868 (12) | 166.5 (19) |
N1—H1A···O1 | 0.918 (14) | 1.875 (14) | 2.7658 (13) | 162.9 (14) |
O4—H4···O3iv | 1.02 (4) | 1.60 (4) | 2.6115 (14) | 173 (4) |
O5—H5···O2v | 0.92 (3) | 1.77 (3) | 2.6747 (15) | 168.7 (19) |
C7—H7···O6 | 0.994 (18) | 2.51 (2) | 2.8580 (19) | 100.1 (12) |
C10—H10···O2iii | 0.973 (15) | 2.550 (16) | 3.2450 (15) | 128.3 (11) |
Symmetry codes: (ii) −x, −y+1, −z+2; (iii) x+1, y, z; (iv) −x, −y+2, −z+1; (v) x+1, y−1, z. |
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