Crystal structure, vibrational frequencies and polarizability distribution in hydrogen-bonded salts of pyromellitic acid

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.

Computing details

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)

Crystal data

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) Å^3	0.40 × 0.37 × 0.35 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0516P)^2 + 0.4163P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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)	C2^i—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—C3^i	119.75 (9)	C7—C6—H6	123.4 (10)
C3^i—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—C2^i	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)	C3^i—C2—C5—O3	162.41 (9)
C3—C1—C2—C5	179.02 (8)	C1—C2—C3^i—C1^i	0.56 (14)
C4—C1—C2—C3^i	176.95 (8)	C5—C2—C3^i—C1^i	−179.00 (8)
C2—C1—C3—C2^i	0.56 (14)	C3^i—C2—C5—O4	−18.34 (12)
C4—C1—C3—C2^i	−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—C3^i	−0.55 (13)	C8—C9—C10—N1	−0.39 (16)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ii	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···O6^iii	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···O2^iv	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···O1^v	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···O4^vi	0.982 (16)	2.382 (16)	3.3566 (13)	171.5 (13)
C9—H9···O2^vii	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)

Crystal data

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) Å^3	0.20 × 0.15 × 0.15 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0584P)^2 + 0.3182P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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—C3^i	117.52 (8)	O5—C11—C7	113.09 (8)
C1—C2—C5	129.45 (8)	O6—C11—C7	122.31 (9)
C3^i—C2—C5	113.02 (8)	N1—C6—H6	118.1 (9)
C1—C3—C2^i	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)
C2^i—C3—H3	117.5 (8)
C10—N1—C6—C7	0.16 (15)	C1—C2—C3^i—C1^i	−0.35 (14)
C6—N1—C10—C9	−0.45 (15)	C5—C2—C3^i—C1^i	−179.68 (9)
C3—C1—C2—C5	179.53 (9)	C3^i—C2—C5—O4	175.16 (9)
C4—C1—C2—C3^i	179.78 (9)	C1—C2—C5—O3	177.01 (10)
C2—C1—C3—C2^i	−0.35 (14)	N1—C6—C7—C8	0.27 (14)
C4—C1—C3—C2^i	−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—C3^i	0.32 (13)	C8—C7—C11—O6	−177.19 (10)
C1—C2—C5—O4	−4.08 (15)	C7—C8—C9—C10	0.11 (15)
C3^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	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···O4^iii	0.91 (2)	1.73 (2)	2.6308 (11)	174.3 (19)
C6—H6···O6^iv	0.952 (15)	2.212 (15)	3.1005 (12)	154.9 (12)
C9—H9···O1^v	0.970 (15)	2.404 (15)	3.0964 (13)	128.0 (11)
C9—H9···O3^vi	0.970 (15)	2.440 (15)	3.1921 (13)	134.1 (11)
C10—H10···O1^ii	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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0646P)^2 + 0.0629P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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)	C2^i—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—C3^i	117.38 (9)	O5—C12—C8	112.69 (10)
C3^i—C2—C5	114.15 (9)	C6—C7—H7	120.4 (8)
C1—C3—C2^i	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—C3^i—C1^i	−179.78 (10)
C3—C1—C2—C3^i	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—C3^i	−178.95 (10)	N1—C6—C11—C10	−179.12 (10)
C2—C1—C3—C2^i	−0.12 (16)	C7—C6—C11—C10	0.16 (17)
C4—C1—C3—C2^i	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)
C3^i—C2—C5—O3	−1.48 (14)	C9—C8—C12—O6	174.67 (11)
C3^i—C2—C5—O4	177.64 (10)	C8—C9—C10—C11	−0.03 (17)
C1—C2—C3^i—C1^i	−0.12 (16)	C9—C10—C11—C6	0.23 (17)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7^ii	0.951 (16)	1.946 (16)	2.8874 (14)	170.2 (14)
N1—H1B···O7^iii	0.922 (15)	1.980 (15)	2.8740 (14)	162.9 (14)
N1—H1C···O1^iv	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···O3^v	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···O3^vi	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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.118	w = 1/[σ^2(Fo^2) + (0.0593P)^2 + 0.163P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.127 (10)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

O1—C4	1.2525 (13)	C1—C3^i	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)
C3^i—C1—C4	117.84 (9)	O5—C12—O6	123.54 (13)
C2—C1—C3^i	118.89 (9)	O5—C12—C9	112.31 (11)
C2—C1—C4	123.25 (10)	O6—C12—C9	124.14 (12)
C2—C3—C1^i	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)
C1^i—C3—H3	119.9 (10)	C10—C11—H11	122.0 (11)
C2—C3—H3	119.3 (10)
C5—C2—C1—C3	176.83 (9)	C3^i—C1—C4—O2	−76.17 (13)
C5—C2—C1—C4	−4.84 (15)	N1—C6—C7—C8	179.15 (10)
C3^i—C2—C1—C3	0.07 (13)	C11—C6—C7—C8	0.61 (16)
C3^i—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—C1^i	−0.07 (14)	C8—C9—C10—C11	−0.45 (17)
C5—C2—C3—C1^i	−176.82 (9)	C12—C9—C10—C11	−178.04 (10)
C2—C1—C3^i—C2^i	−0.07 (13)	C8—C9—C12—O5	−1.28 (15)
C4—C1—C3^i—C2^i	−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)
C3^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1^i	0.959 (19)	1.82 (2)	2.7570 (13)	165.5 (15)
N1—H1B···O1^ii	0.943 (18)	1.821 (19)	2.7176 (12)	157.8 (18)
N1—H1C···O2^iii	0.909 (19)	1.980 (19)	2.8633 (13)	163.6 (17)
O4—H4···O3^iv	0.92 (3)	1.69 (3)	2.6032 (14)	174 (2)
O5—H5···O2^v	0.94 (3)	1.74 (3)	2.6627 (15)	171.3 (18)
C7—H7···O2^iii	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)

Crystal data

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) Å^3	0.40 × 0.37 × 0.35 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 0.86	w = 1/[σ^2(Fo^2) + (0.0692P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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)	C2^i—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—C3^i	119.30 (8)	C7—C6—H6	122.9 (9)
C3^i—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—C2^i	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)	C3^i—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—C3^i	176.89 (7)	C5—C2—C3^i—C1^i	−178.97 (7)
C2—C1—C3—C2^i	0.59 (11)	C3^i—C2—C5—O4	−19.05 (11)
C4—C1—C2—C5	−3.55 (11)	C1—C2—C3^i—C1^i	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—C2^i	−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—C3^i	−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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1^ii	0.965 (16)	1.709 (16)	2.6576 (11)	166.8 (15)
N2—H2B···O3^iii	0.88 (3)	2.41 (3)	3.1900 (18)	148 (3)
O4—H4···O6^iv	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···O2^v	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···O1^vi	0.87 (2)	1.93 (2)	2.7936 (13)	172 (2)
C6—H6···O3^iii	0.985 (14)	2.262 (15)	3.1137 (15)	144.2 (12)
C8—H8···O4^vii	0.978 (18)	2.414 (18)	3.3862 (13)	173.1 (13)
C9—H9···O2^v	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)

Crystal data

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) Å^3	0.20 × 0.15 × 0.15 mm
Z = 2

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0527P)^2] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	1.3816 (16)	C10—H10	1.001 (14)
C2—C1	1.4136 (16)
C5—O4—H4	113.5 (10)	C2^i—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)
C3^i—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—C3^i	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—C3^i—C1^i	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—C2^i	−0.15 (19)
C6—N1—C10—C9	0.6 (2)	C4—C1—C3—C2^i	179.69 (12)
C3^i—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—C3^i—C1^i	−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)
C3^i—C2—C5—O3	2.88 (18)	C6—C7—C11—O6	−1.9 (2)
C3^i—C2—C5—O4	−175.96 (12)	C8—C7—C11—O5	−1.53 (19)
C3^i—C2—C1—C3	0.14 (17)	C8—C7—C11—O6	177.05 (13)
C5—C2—C3^i—C1^i	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)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^ii	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···O4^iii	0.92 (2)	1.71 (2)	2.6302 (14)	177 (2)
C6—H6···O6^iv	0.958 (15)	2.220 (15)	3.1231 (17)	156.8 (12)
C9—H9···O3^v	0.977 (15)	2.505 (15)	3.2231 (17)	130.2 (11)
C9—H9···O1^vi	0.977 (15)	2.410 (15)	3.1394 (17)	131.0 (11)
C10—H10···O1^ii	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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0706P)^2 + 0.1136P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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)
C3^i—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—C3^i	117.46 (10)	C9—C8—C12	120.81 (11)
C1—C3—C2^i	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)
C2^i—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—C3^i—C1^i	−179.71 (11)
C3—C1—C2—C3^i	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—C3^i	−178.94 (11)	N1—C6—C11—C10	−179.31 (12)
C2—C1—C3—C2^i	−0.02 (18)	C7—C6—C11—C10	−0.15 (19)
C4—C1—C3—C2^i	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)
C3^i—C2—C5—O3	−1.53 (16)	C9—C8—C12—O6	174.47 (13)
C3^i—C2—C5—O4	177.78 (11)	C8—C9—C10—C11	−0.2 (2)
C1—C2—C3^i—C1^i	−0.03 (18)	C9—C10—C11—C6	0.6 (2)

Symmetry code: (i) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O7^ii	0.94 (2)	1.98 (2)	2.9072 (16)	167.4 (18)
N1—H1B···O7^iii	0.93 (2)	1.99 (2)	2.8938 (17)	161.7 (15)
N1—H1C···O1^iv	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···O3^v	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···O3^vi	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)

Crystal data

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) Å^3

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.134	w = 1/[σ^2(Fo^2) + (0.0817P)^2 + 0.0909P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (11)

Special details

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—C3^i	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—C1^i—C4^i	117.86 (7)	C8—C9—C10	121.57 (11)
C2—C1—C3^i	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—C3^i—C2^i	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—C3^i—H3^i	118.1 (10)	C10—C11—H11	118.2 (12)
C3^i—C1—C2—C5	177.21 (8)	C5—C2—C3—C1^i	−177.23 (8)
C3—C1—C2—C3^i	−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—C3^i—C2^i	−0.20 (12)	C12—C6—C11—C10	−177.71 (10)
C4—C1—C3^i—C2^i	−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)
C3^i—C1—C4—O1	100.25 (10)	C11—C6—C12—O6	−178.71 (13)
C3^i—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—C1^i	−0.20 (13)	C9—C10—C11—C6	0.14 (16)

Symmetry code: (i) −x, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1^ii	0.946 (18)	1.809 (18)	2.7220 (12)	161.5 (13)
N1—H1C···O2^iii	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···O3^iv	1.02 (4)	1.60 (4)	2.6115 (14)	173 (4)
O5—H5···O2^v	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···O2^iii	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.