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The crystal structures of dilithium, disodium and diammonium terephthalate (1,4-benzenedicarboxylate) have been solved ab initio using Monte Carlo simulated annealing techniques, and refined using synchrotron powder data. The structures of dipotassium terephthalate, potassium hydrogen terephthalate and ammonium hydrogen terephthalate have been refined using single-crystal techniques. Li2C8H4O4 crystallizes in P21c, with a = 8.35921 (5), b = 5.13208 (2), c = 8.48490 (5) Å, β = 93.1552 (4)°, V = 363.451 (3) Å3, Z = 2. The Li anions are tetrahedrally coordinated and the packing of the terephthalate anions resembles the γ-packing of aromatic hydrocarbons. Na2C8H4O4 crystallizes in Pbc21, with a = 3.54804 (5), b = 10.81604 (16), c = 18.99430 (20) Å, V = 728.92 (2) Å3, Z = 4. The coordination of the two independent Na is trigonal prismatic and the terephthalate packing resembles the β packing of hydrocarbons. (NH4)2C8H4O4 also crystallizes in Pbc21, with a = 4.0053 (5), b = 11.8136 (21), c = 20.1857 (24) Å, V = 955.1 (2) Å3, Z = 4. The cations and planar anions are linked by hydrogen bonds and the packing is a looser version of the β packing. K2C8H4O2 crystallizes in P21c, with a = 10.561 (4), b = 3.9440 (12), c = 11.535 (5) Å, β = 113.08 (3)°, V = 442.0 (3) Å3, Z = 2. The K is trigonal prismatic and the packing is also β. Both KHC8H4O4 and (NH4)HC8H4O4 crystallize in C2/c, with a = 18.825 (4) and 18.924 (4), b = 3.770 (2) and 3.7967 (9), c = 11.179 (2) and 11.481 (2) Å, β = 98.04 (3) and 94.56 (5)°, V = 816.8 (3) and 790.9 (3) Å3, respectively, and Z = 4. The packing in the hydrogen-bonded acid salts is also β. Electrostatic interactions among the terephthalate anions appear to be important in determining the crystal packing.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768199014718/bk0069sup1.cif
Contains datablocks Na2tph01, amm2tph, K2tph, Ktph, ammHtph, global, Li2tph

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069K2tphsup2.hkl
Contains datablock che3=20

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069Ktphsup3.hkl
Contains datablock che2=20

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069ammHtphsup4.hkl
Contains datablock c136=20

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069amm2tphsup5.rtv
Contains datablock amm2tph

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069li2tphsup6.rtv
Contains datablock Li2tph

rtv

Rietveld powder data file (CIF format) https://doi.org/10.1107/S0108768199014718/bk0069Na2tph01sup7.rtv
Contains datablock Na2tph01

CCDC references: 145817; 145818; 145819; 145820; 145821; 145822

Computing details top

Data collection: P3 for K2tph. Cell refinement: P3 for K2tph. Data reduction: XTAPE for K2tph. Program(s) used to solve structure: SHELXS97 (Sheldrick, 1990) for K2tph, Ktph, ammHtph. Program(s) used to refine structure: GSAS for Li2tph, Na2tph01, amm2tph; SHELXL97 (Sheldrick, 1997) for K2tph, Ktph, ammHtph.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
[Figure 13]
[Figure 14]
(Li2tph) top
Crystal data top
C8H4Li2O4β = 93.1555 (4)°
Mr = ?V = ? Å3
Monoclinic, P21/cZ = 4
a = 8.35918 (5) Å? radiation, λ = 1.149681 Å
b = 5.13212 (3) Å?, ? × ? × ? mm
c = 8.48489 (5) Å
Data collection top
2θmin = 7.005°, 2θmax = 56.835°, 2θstep = 0.005°
Refinement top
Rp = 0.0769967 data points
Rwp = 0.09844 parameters
Rexp = 0.0708 restraints
χ2 = 2.016(Δ/σ)max = 0.07
Crystal data top
C8H4Li2O4β = 93.1555 (4)°
Mr = ?V = ? Å3
Monoclinic, P21/cZ = 4
a = 8.35918 (5) Å? radiation, λ = 1.149681 Å
b = 5.13212 (3) Å?, ? × ? × ? mm
c = 8.48489 (5) Å
Data collection top
2θmin = 7.005°, 2θmax = 56.835°, 2θstep = 0.005°
Refinement top
Rp = 0.0769967 data points
Rwp = 0.09844 parameters
Rexp = 0.0708 restraints
χ2 = 2.016
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
H50.1224 (4)0.2834 (5)0.1794 (3)0.05*.5
C10.15701 (9)0.0493 (5)0.0440 (3)0.0246 (8)*.5
C20.072380.167740.106230.0246 (8)*.5
C30.084630.217080.062270.0246 (8)*.5
H20.12230.28340.179480.05*.5
H30.14300.36680.105210.05*.5
C70.3181 (3)0.1142 (6)0.1018 (4)0.0339 (7)*
O80.3862 (2)0.0445 (4)0.1902 (3)0.0339 (7)*
O90.3809 (3)0.3274 (4)0.0532 (3)0.0339 (7)*
Li0.4878 (8)0.1136 (13)0.3556 (8)0.035 (2)*
(Na2tph01) top
Crystal data top
C8H4Na2O4c = 18.9943 (2) Å
Mr = ?V = ? Å3
Orthorhombic, Pbc21Z = 4
a = 3.54807 (5) Å? radiation, λ = 1.149681 Å
b = 10.81599 (16) Å × × mm
Data collection top
h = ??l = ??
k = ??
Refinement top
S = 2.6016 restraints
53 parameters(Δ/σ)max = 0.10
Crystal data top
C8H4Na2O4c = 18.9943 (2) Å
Mr = ?V = ? Å3
Orthorhombic, Pbc21Z = 4
a = 3.54807 (5) Å? radiation, λ = 1.149681 Å
b = 10.81599 (16) Å × × mm
Data collection top
Refinement top
S = 2.6016 restraints
53 parameters(Δ/σ)max = 0.10
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.147 (4)0.0979 (19)0.0964 (18)0.049 (3)*
C20.3340.00920.05480.049 (3)*
C30.4340.03730.01520.049 (3)*
C40.3460.15410.04370.049 (3)*
C50.1590.24290.00210.049 (3)*
C60.0590.21480.06790.049 (3)*
H20.3940.07140.07440.04*
H30.5630.02390.04390.04*
H50.0980.32350.02170.04*
H60.0700.27600.09660.04*
C70.058 (7)0.0783 (19)0.1727 (18)0.0187 (15)*
C80.419 (7)0.175 (2)0.1208 (17)0.0187*
O10.024 (4)0.032 (2)0.1976 (19)0.0187*
O20.038 (4)0.168 (2)0.2133 (19)0.0187*
O30.484 (4)0.286 (2)0.1426 (19)0.0187*
O40.503 (5)0.083 (2)0.1574 (18)0.0187*
Na11.014 (4)0.571 (3)0.1772 (3)0.0226 (13)*
Na20.479 (2)0.319 (3)0.2725300.0226 (13)*
(Na2tph02) top
Crystal data top
C8H4Na2O4β = 106.437 (7)°
Mr = ?V = ? Å3
Monoclinic, C2/cZ = 4
a = 20.4146 (15) Å? radiation, λ = 1.149681 Å
b = 3.4910 (2) Å?, ? × ? × ? mm
c = 10.3282 (8) Å
Data collection top
2θmin = 6.005°, 2θmax = 54.995°, 2θstep = 0.005°
Refinement top
Rp = 0.149χ2 = NOT FOUND
Rwp = 0.2009799 data points
Rexp = 0.077
Crystal data top
C8H4Na2O4β = 106.437 (7)°
Mr = ?V = ? Å3
Monoclinic, C2/cZ = 4
a = 20.4146 (15) Å? radiation, λ = 1.149681 Å
b = 3.4910 (2) Å?, ? × ? × ? mm
c = 10.3282 (8) Å
Data collection top
2θmin = 6.005°, 2θmax = 54.995°, 2θstep = 0.005°
Refinement top
Rp = 0.149χ2 = NOT FOUND
Rwp = 0.2009799 data points
Rexp = 0.077
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Na0.00.74640.250.02*
Na20.150660.16450.425890.02*
C0.093050.26530.103520.02*
O10.151140.39950.102030.02*
O20.054390.1310.988040.02*
O30.07240.25330.207630.02*
O40.212050.66460.354450.02*
H10.1940.6120.2690.04*
H20.2480.7240.3620.04*
H30.0220.0350.9960.04*.5
(amm2tph) top
Crystal data top
C8H16N2O4c = 20.186 (2) Å
Mr = ?V = ? Å3
Orthorhombic, Pbc21Z = 4
a = 4.0053 (5) Å? radiation, λ = 1.540629 Å
b = 11.814 (2) Å?, ? × ? × ? mm
Data collection top
2θmin = 8.043°, 2θmax = 69.983°, 2θstep = 0.02°
Refinement top
Rp = 0.1343098 data points
Rwp = 0.17938 parameters
Rexp = 0.06610 restraints
χ2 = 7.344(Δ/σ)max = 0.11
Crystal data top
C8H16N2O4c = 20.186 (2) Å
Mr = ?V = ? Å3
Orthorhombic, Pbc21Z = 4
a = 4.0053 (5) Å? radiation, λ = 1.540629 Å
b = 11.814 (2) Å?, ? × ? × ? mm
Data collection top
2θmin = 8.043°, 2θmax = 69.983°, 2θstep = 0.02°
Refinement top
Rp = 0.1343098 data points
Rwp = 0.17938 parameters
Rexp = 0.06610 restraints
χ2 = 7.344(Δ/σ)max = 0.11
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.157 (5)0.0853 (11)0.0389 (13)0.043 (6)*
C20.0880.19340.01520.043 (6)*
C30.1710.22220.04960.043 (6)*
C40.3230.14290.09070.043 (6)*
C50.3920.03480.06700.043 (6)*
C60.3090.00590.00220.043 (6)*
C70.0670.05410.10890.004 (3)*
C80.4130.17400.16070.004 (3)*
H20.0170.24810.04360.06*
H30.1230.29680.06590.06*
H50.4970.01990.09530.06*
H60.3570.06860.01420.06*
O90.070 (5)0.1366 (19)0.151680.004 (3)*
O100.001 (5)0.0464 (17)0.127 (2)0.004 (3)*
O110.550 (5)0.107 (2)0.1998 (8)0.004 (3)*
O120.483 (5)0.2860 (16)0.168 (2)0.004 (3)*
N130.504 (4)0.190 (3)0.178 (2)0.04*
H13a0.4450.26350.17470.06*
H13b0.3290.14620.16710.06*
H13c0.6740.17630.14980.06*
H13d0.5690.17500.21950.06*
N140.933 (6)0.923 (3)0.282 (2)0.04*
H14a1.0840.86660.27840.06*
H14b0.9110.94280.32460.06*
H14c1.0010.98270.25800.06*
H14d0.7350.89830.26620.06*
(K2tph) top
Crystal data top
C8H4K2O4F(000) = 244
Mr = 242.31Dx = 1.821 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.561 (4) ÅCell parameters from 19 reflections
b = 3.9440 (12) Åθ = 5.5–11.4°
c = 11.535 (5) ŵ = 1.05 mm1
β = 113.08 (3)°T = 293 K
V = 442.0 (3) Å3Needle, colourless
Z = 20.45 × 0.05 × 0.05 mm
Data collection top
Scintillation counter
diffractometer
Rint = 0.023
Radiation source: fine-focus sealed tubeh = 011
Graphite monochromatork = 44
θ–2θ scansl = 1211
1130 measured reflections5 standard reflections every 200 reflections
584 independent reflections intensity decay: none
497 reflections with I > 2σ(I)
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.061H atoms treated by a mixture of independent and constrained refinement
S = 1.07 w = 1/[σ2(Fo2) + (0.0339P)2 + 0.0595P]
where P = (Fo2 + 2Fc2)/3
584 reflections(Δ/σ)max = 0.010
66 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C8H4K2O4V = 442.0 (3) Å3
Mr = 242.31Z = 2
Monoclinic, P21/cMo Kα radiation
a = 10.561 (4) ŵ = 1.05 mm1
b = 3.9440 (12) ÅT = 293 K
c = 11.535 (5) Å0.45 × 0.05 × 0.05 mm
β = 113.08 (3)°
Data collection top
Scintillation counter
diffractometer
Rint = 0.023
1130 measured reflections5 standard reflections every 200 reflections
584 independent reflections intensity decay: none
497 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.061H atoms treated by a mixture of independent and constrained refinement
S = 1.07Δρmax = 0.22 e Å3
584 reflectionsΔρmin = 0.19 e Å3
66 parameters
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
K10.61068 (6)0.20395 (14)0.16167 (5)0.0268 (2)
O10.35218 (18)0.1856 (5)0.16464 (16)0.0290 (5)
O20.32648 (19)0.3005 (5)0.03264 (17)0.0291 (5)
C70.2822 (3)0.2858 (6)0.0541 (2)0.0207 (6)
C10.1358 (3)0.3988 (6)0.0259 (2)0.0214 (6)
C20.0787 (3)0.3548 (7)0.1146 (2)0.0244 (7)
H2A0.13120.25750.19210.027 (7)*
C60.0548 (3)0.5466 (7)0.0895 (2)0.0255 (7)
H6A0.09130.57890.15020.029 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K10.0284 (4)0.0280 (4)0.0273 (4)0.0002 (3)0.0146 (3)0.0010 (3)
O10.0230 (10)0.0399 (12)0.0230 (11)0.0045 (9)0.0078 (9)0.0071 (9)
O20.0274 (10)0.0368 (12)0.0292 (10)0.0055 (9)0.0176 (9)0.0009 (9)
C70.0213 (14)0.0176 (14)0.0253 (15)0.0013 (11)0.0114 (13)0.0028 (11)
C10.0226 (14)0.0210 (14)0.0215 (14)0.0025 (12)0.0097 (12)0.0023 (11)
C20.0219 (15)0.0309 (16)0.0195 (14)0.0041 (12)0.0071 (12)0.0050 (11)
C60.0272 (16)0.0321 (16)0.0218 (14)0.0002 (13)0.0146 (12)0.0021 (12)
Geometric parameters (Å, º) top
K1—O1i2.676 (2)O1—C71.260 (3)
K1—O2ii2.693 (2)O1—K1iv2.676 (2)
K1—O2iii2.718 (2)O1—K1i2.780 (2)
K1—O12.745 (2)O2—C71.261 (3)
K1—O1iv2.780 (2)O2—K1ii2.693 (2)
K1—O22.984 (2)O2—K1iii2.718 (2)
K1—C73.209 (3)C7—C11.517 (4)
K1—C7iv3.441 (3)C7—K1i3.441 (3)
K1—K1iii3.889 (2)C1—C21.387 (4)
K1—K1v3.9440 (12)C1—C61.397 (4)
K1—K1vi3.9440 (12)C2—C6vii1.380 (4)
K1—K1iv4.1523 (15)C6—C2vii1.380 (4)
O1i—K1—O2ii84.43 (7)O2iii—K1—K1vi42.95 (4)
O1i—K1—O2iii159.07 (6)O1—K1—K1vi88.49 (4)
O2ii—K1—O2iii93.59 (6)O1iv—K1—K1vi42.67 (4)
O1i—K1—O182.18 (6)O2—K1—K1vi97.33 (4)
O2ii—K1—O1119.20 (6)C7—K1—K1vi95.77 (5)
O2iii—K1—O1116.43 (6)C7iv—K1—K1vi61.36 (5)
O1i—K1—O1iv92.55 (6)K1iii—K1—K1vi65.57 (2)
O2ii—K1—O1iv159.44 (6)K1v—K1—K1vi180.0
O2iii—K1—O1iv81.99 (6)O1i—K1—K1iv85.14 (5)
O1—K1—O1iv80.31 (6)O2ii—K1—K1iv157.54 (4)
O1i—K1—O2106.31 (6)O2iii—K1—K1iv103.09 (5)
O2ii—K1—O283.42 (6)O1—K1—K1iv39.40 (4)
O2iii—K1—O294.11 (6)O1iv—K1—K1iv40.95 (4)
O1—K1—O245.58 (6)O2—K1—K1iv80.51 (5)
O1iv—K1—O2116.83 (6)C7—K1—K1iv60.42 (5)
O1i—K1—C792.12 (7)C7iv—K1—K1iv48.91 (5)
O2ii—K1—C7100.17 (7)K1iii—K1—K1iv91.82 (4)
O2iii—K1—C7108.71 (6)K1v—K1—K1iv118.354 (13)
O1—K1—C722.76 (6)K1vi—K1—K1iv61.646 (13)
O1iv—K1—C7100.27 (6)C7—O1—K1iv146.68 (16)
O2—K1—C723.13 (6)C7—O1—K199.82 (15)
O1i—K1—C7iv74.33 (7)K1iv—O1—K199.99 (6)
O2ii—K1—C7iv144.53 (6)C7—O1—K1i111.08 (15)
O2iii—K1—C7iv96.39 (7)K1iv—O1—K1i92.55 (6)
O1—K1—C7iv86.13 (6)K1—O1—K1i97.45 (6)
O1iv—K1—C7iv19.98 (6)C7—O2—K1ii136.08 (16)
O2—K1—C7iv129.42 (6)C7—O2—K1iii130.32 (16)
C7—K1—C7iv108.55 (6)K1ii—O2—K1iii93.59 (6)
O1i—K1—K1iii150.25 (5)C7—O2—K188.54 (15)
O2ii—K1—K1iii87.47 (5)K1ii—O2—K196.58 (6)
O2iii—K1—K1iii49.92 (4)K1iii—O2—K185.89 (6)
O1—K1—K1iii76.95 (5)O1—C7—O2124.4 (2)
O1iv—K1—K1iii104.41 (5)O1—C7—C1116.9 (2)
O2—K1—K1iii44.19 (4)O2—C7—C1118.7 (2)
C7—K1—K1iii61.23 (5)O1—C7—K157.42 (13)
C7iv—K1—K1iii124.39 (6)O2—C7—K168.34 (14)
O1i—K1—K1v44.77 (5)C1—C7—K1165.64 (17)
O2ii—K1—K1v43.46 (4)O1—C7—K1i48.94 (13)
O2iii—K1—K1v137.05 (4)O2—C7—K1i130.44 (17)
O1—K1—K1v91.51 (4)C1—C7—K1i89.43 (14)
O1iv—K1—K1v137.33 (4)K1—C7—K1i77.19 (6)
O2—K1—K1v82.67 (4)C2—C1—C6118.3 (2)
C7—K1—K1v84.23 (5)C2—C1—C7120.4 (2)
C7iv—K1—K1v118.64 (5)C6—C1—C7121.2 (2)
K1iii—K1—K1v114.43 (2)C6vii—C2—C1120.9 (2)
O1i—K1—K1vi135.23 (5)C2vii—C6—C1120.7 (2)
O2ii—K1—K1vi136.54 (4)
Symmetry codes: (i) x+1, y+1/2, z+1/2; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x+1, y1/2, z+1/2; (v) x, y+1, z; (vi) x, y1, z; (vii) x, y+1, z.
(Ktph) top
Crystal data top
C8H5KO4Z = 4
Mr = 204.22F(000) = 416
Monoclinic, C2/cDx = 1.715 Mg m3
a = 18.825 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 3.7700 (8) ŵ = 0.65 mm1
c = 11.179 (2) ÅT = 293 K
β = 94.56 (3)°Plate, colourless
V = 790.9 (3) Å30.42 × 0.10 × 0.04 mm
Data collection top
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 20.0°, θmin = 3.7°
695 measured reflectionsh = 018
376 independent reflectionsk = 33
296 reflections with I > 2σ(I)l = 1010
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0438P)2]
where P = (Fo2 + 2Fc2)/3
376 reflections(Δ/σ)max = 0.017
72 parametersΔρmax = 0.15 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C8H5KO4V = 790.9 (3) Å3
Mr = 204.22Z = 4
Monoclinic, C2/cMo Kα radiation
a = 18.825 (4) ŵ = 0.65 mm1
b = 3.7700 (8) ÅT = 293 K
c = 11.179 (2) Å0.42 × 0.10 × 0.04 mm
β = 94.56 (3)°
Data collection top
695 measured reflectionsRint = 0.029
376 independent reflectionsθmax = 20.0°
296 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0301 restraint
wR(F2) = 0.072H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.15 e Å3
376 reflectionsΔρmin = 0.15 e Å3
72 parameters
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*/UeqOcc. (<1)
K0.00000.3441 (4)0.25000.0458 (6)
O10.08687 (11)0.1788 (8)0.6571 (2)0.0346 (8)
O20.06011 (13)0.0413 (9)0.4658 (2)0.0447 (9)
C40.10416 (17)0.1391 (11)0.5544 (4)0.0248 (10)
C10.17938 (16)0.1986 (10)0.5236 (3)0.0221 (10)
C20.20168 (19)0.1064 (11)0.4125 (4)0.0239 (10)
H20.1735 (17)0.013 (9)0.349 (3)0.011 (9)*
C60.22783 (18)0.3424 (12)0.6104 (4)0.0251 (10)
H60.2123 (17)0.403 (9)0.683 (3)0.026 (10)*
H10.0168 (17)0.08 (2)0.477 (7)0.04 (3)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
K0.0524 (9)0.0419 (9)0.0465 (9)0.0000.0251 (7)0.000
O10.0234 (15)0.055 (2)0.0270 (16)0.0062 (15)0.0102 (12)0.0048 (15)
O20.0135 (16)0.087 (3)0.0332 (17)0.0107 (16)0.0024 (15)0.0042 (17)
C40.016 (2)0.027 (2)0.032 (3)0.004 (2)0.001 (2)0.001 (2)
C10.014 (2)0.021 (2)0.030 (3)0.0034 (19)0.005 (2)0.0007 (19)
C20.021 (2)0.030 (3)0.020 (2)0.005 (2)0.0006 (19)0.004 (2)
C60.024 (2)0.031 (2)0.022 (2)0.003 (2)0.010 (2)0.005 (2)
Geometric parameters (Å, º) top
K—O1i2.694 (3)O1—Kii2.694 (3)
K—O1ii2.694 (3)O1—Kiii2.812 (3)
K—O1iii2.812 (3)O2—C41.293 (4)
K—O1iv2.812 (3)C4—C11.500 (5)
K—O2v2.823 (3)C1—C21.386 (5)
K—O22.823 (3)C1—C61.388 (5)
K—Kvi3.7700 (8)C2—C6viii1.385 (5)
K—Kvii3.7700 (8)C6—C2viii1.385 (5)
O1—C41.227 (4)
O1i—K—O1ii96.22 (13)O2—K—Kvi113.84 (7)
O1i—K—O1iii177.39 (11)O1i—K—Kvii131.89 (6)
O1ii—K—O1iii86.39 (7)O1ii—K—Kvii131.89 (7)
O1i—K—O1iv86.39 (7)O1iii—K—Kvii45.50 (6)
O1ii—K—O1iv177.39 (11)O1iv—K—Kvii45.50 (6)
O1iii—K—O1iv91.00 (12)O2v—K—Kvii66.16 (7)
O1i—K—O2v98.91 (8)O2—K—Kvii66.16 (7)
O1ii—K—O2v112.64 (8)Kvi—K—Kvii180.0
O1iii—K—O2v80.03 (8)C4—O1—Kii131.0 (2)
O1iv—K—O2v66.82 (8)C4—O1—Kiii117.7 (2)
O1i—K—O2112.64 (8)Kii—O1—Kiii86.39 (7)
O1ii—K—O298.91 (8)C4—O2—K136.7 (3)
O1iii—K—O266.82 (8)O1—C4—O2123.3 (3)
O1iv—K—O280.03 (8)O1—C4—C1121.5 (3)
O2v—K—O2132.31 (15)O2—C4—C1115.2 (3)
O1i—K—Kvi48.11 (6)C2—C1—C6119.7 (3)
O1ii—K—Kvi48.11 (7)C2—C1—C4121.8 (3)
O1iii—K—Kvi134.50 (6)C6—C1—C4118.5 (3)
O1iv—K—Kvi134.50 (6)C6viii—C2—C1119.6 (4)
O2v—K—Kvi113.84 (7)C2viii—C6—C1120.7 (4)
Symmetry codes: (i) x, y+1, z1/2; (ii) x, y+1, z+1; (iii) x, y, z+1; (iv) x, y, z1/2; (v) x, y, z+1/2; (vi) x, y+1, z; (vii) x, y1, z; (viii) x+1/2, y+1/2, z+1.
(ammHtph) top
Crystal data top
C8H9NO4Z = 4
Mr = 183.16F(000) = 384
Monoclinic, C2/cDx = 1.489 Mg m3
a = 18.924 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 3.7967 (8) ŵ = 0.12 mm1
c = 11.481 (2) ÅT = 293 K
β = 98.04 (3)°Plate, colourless
V = 816.8 (3) Å30.3 × 0.2 × 0.05 mm
Data collection top
Radiation source: fine-focus sealed tubeRint = 0.019
Graphite monochromatorθmax = 20.0°, θmin = 3.6°
785 measured reflectionsh = 1818
373 independent reflectionsk = 33
307 reflections with I > 2σ(I)l = 1111
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.029Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0536P)2]
where P = (Fo2 + 2Fc2)/3
373 reflections(Δ/σ)max = 0.243
80 parametersΔρmax = 0.11 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C8H9NO4V = 816.8 (3) Å3
Mr = 183.16Z = 4
Monoclinic, C2/cMo Kα radiation
a = 18.924 (4) ŵ = 0.12 mm1
b = 3.7967 (8) ÅT = 293 K
c = 11.481 (2) Å0.3 × 0.2 × 0.05 mm
β = 98.04 (3)°
Data collection top
785 measured reflectionsRint = 0.019
373 independent reflectionsθmax = 20.0°
307 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0291 restraint
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.00(Δ/σ)max = 0.243
373 reflectionsΔρmax = 0.11 e Å3
80 parametersΔρmin = 0.18 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.09478 (9)0.1447 (5)0.65460 (15)0.0429 (7)
O20.05923 (10)0.0337 (6)0.46591 (16)0.0454 (7)
C40.10757 (14)0.1194 (7)0.5524 (2)0.0307 (8)
C10.18055 (13)0.1862 (6)0.5232 (2)0.0246 (8)
C20.19949 (14)0.1088 (7)0.4134 (2)0.0287 (8)
C60.23173 (14)0.3281 (7)0.6095 (2)0.0295 (8)
H2A0.1644 (13)0.004 (6)0.354 (2)0.031 (7)*
H6A0.2178 (12)0.383 (7)0.685 (2)0.037 (7)*
N10.50000.0908 (14)0.75000.0459 (10)
H10.5335 (19)0.046 (10)0.721 (3)0.080 (12)*
H20.475 (2)0.189 (12)0.688 (4)0.106 (17)*
H30.021 (2)0.00 (2)0.496 (6)0.050 (18)*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0298 (12)0.0699 (15)0.0310 (12)0.0041 (10)0.0114 (8)0.0016 (10)
O20.0209 (12)0.0811 (16)0.0341 (12)0.0141 (13)0.0034 (10)0.0001 (11)
C40.0244 (19)0.0352 (17)0.0324 (17)0.0015 (13)0.0038 (15)0.0018 (14)
C10.0197 (17)0.0289 (15)0.0250 (15)0.0020 (13)0.0024 (15)0.0006 (13)
C20.0219 (18)0.0352 (16)0.0276 (15)0.0046 (14)0.0015 (14)0.0031 (14)
C60.029 (2)0.0373 (18)0.0231 (16)0.0007 (14)0.0065 (15)0.0002 (14)
N10.049 (3)0.050 (3)0.042 (3)0.0000.020 (3)0.000
Geometric parameters (Å, º) top
O1—C41.235 (3)C1—C61.393 (3)
O2—C41.294 (3)C2—C6i1.384 (4)
C4—C11.488 (3)C6—C2i1.384 (4)
C1—C21.390 (3)
O1—C4—O2122.5 (2)C2—C1—C4122.2 (2)
O1—C4—C1120.8 (2)C6—C1—C4118.8 (2)
O2—C4—C1116.7 (2)C1—C2—C6i120.3 (2)
C2—C1—C6119.0 (2)C2i—C6—C1120.7 (2)
Symmetry code: (i) x+1/2, y+1/2, z+1.

Experimental details

(Li2tph)(Na2tph01)(Na2tph02)(amm2tph)
Crystal data
Chemical formulaC8H4Li2O4C8H4Na2O4C8H4Na2O4C8H16N2O4
Mr????
Crystal system, space groupMonoclinic, P21/cOrthorhombic, Pbc21Monoclinic, C2/cOrthorhombic, Pbc21
Temperature (K)????
a, b, c (Å)8.35918 (5), 5.13212 (3), 8.48489 (5)3.54807 (5), 10.81599 (16), 18.9943 (2)20.4146 (15), 3.4910 (2), 10.3282 (8)4.0053 (5), 11.814 (2), 20.186 (2)
α, β, γ (°)90, 93.1555 (4), 9090, 90, 9090, 106.437 (7), 9090, 90, 90
V3)????
Z4444
Radiation type?, λ = 1.149681 Å?, λ = 1.149681 Å?, λ = 1.149681 Å?, λ = 1.540629 Å
µ (mm1)?
Specimen shape, size (mm)?, ? × ? × ? × × ?, ? × ? × ??, ? × ? × ?
Data collection
Diffractometer????
Specimen mounting???
Data collection mode???
Data collection method????
Absorption correction?
No. of measured, independent and
observed reflections
?, ?, ? (?)
Rint?
θ values (°)2θmin = 7.005 2θmax = 56.835 2θstep = 0.005θmax = ?2θmin = 6.005 2θmax = 54.995 2θstep = 0.0052θmin = 8.043 2θmax = 69.983 2θstep = 0.02
Distance from source to specimen (mm)
Refinement
R factors and goodness of fitRp = 0.076, Rwp = 0.098, Rexp = 0.070, χ2 = 2.016R[F2 > 2σ(F2)] = ?, wR(F2) = ?, S = 2.60Rp = 0.149, Rwp = 0.200, Rexp = 0.077, χ2 = NOT FOUNDRp = 0.134, Rwp = 0.179, Rexp = 0.066, χ2 = 7.344
No. of reflections/data points9967?97993098
No. of parameters4453?38
No. of restraints816?10
H-atom treatment????
(Δ/σ)max0.070.10?0.11
Δρmax, Δρmin (e Å3)?, ?


(K2tph)(Ktph)(ammHtph)
Crystal data
Chemical formulaC8H4K2O4C8H5KO4C8H9NO4
Mr242.31204.22183.16
Crystal system, space groupMonoclinic, P21/cMonoclinic, C2/cMonoclinic, C2/c
Temperature (K)293293293
a, b, c (Å)10.561 (4), 3.9440 (12), 11.535 (5)18.825 (4), 3.7700 (8), 11.179 (2)18.924 (4), 3.7967 (8), 11.481 (2)
α, β, γ (°)90, 113.08 (3), 9090, 94.56 (3), 9090, 98.04 (3), 90
V3)442.0 (3)790.9 (3)816.8 (3)
Z244
Radiation typeMo KαMo KαMo Kα
µ (mm1)1.050.650.12
Specimen shape, size (mm)0.45 × 0.05 × 0.050.42 × 0.10 × 0.040.3 × 0.2 × 0.05
Data collection
DiffractometerScintillation counter
diffractometer
??
Specimen mounting
Data collection mode
Data collection methodθ–2θ scans??
Absorption correction
No. of measured, independent and
observed reflections
1130, 584, 497 [I > 2σ(I)]695, 376, 296 [I > 2σ(I)]785, 373, 307 [I > 2σ(I)]
Rint0.0230.0290.019
θ values (°)θmax = ?θmax = 20.0, θmin = 3.7θmax = 20.0, θmin = 3.6
Distance from source to specimen (mm)0.4820.481
Refinement
R factors and goodness of fitR[F2 > 2σ(F2)] = 0.025, wR(F2) = 0.061, S = 1.07R[F2 > 2σ(F2)] = 0.030, wR(F2) = 0.072, S = 1.02R[F2 > 2σ(F2)] = 0.029, wR(F2) = 0.076, S = 1.00
No. of reflections/data points584376373
No. of parameters667280
No. of restraints011
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
(Δ/σ)max0.0100.0170.243
Δρmax, Δρmin (e Å3)0.22, 0.190.15, 0.150.11, 0.18

Computer programs: P3, XTAPE, SHELXS97 (Sheldrick, 1990), GSAS, SHELXL97 (Sheldrick, 1997).

 

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