A proton transfer compound: propane-1,3-di­aminium–pyridine-2,6-dicarboxyl­ate–pyridine-2,6-dicarboxylic acid–water (2/2/2/5)

Aghabozorg, H.; Ghadermazi, M.; Ramezanipour, F.

doi:10.1107/S1600536806005393

A proton transfer compound: propane-1,3-diaminium-pyridine-2,6-dicarboxylate-pyridine-2,6-dicarboxylic acid-water (2/2/2/5)

H. Aghabozorg, M. Ghadermazi and F. Ramezanipour

The title compound, C₃H₁₂N₂²⁺·C₇H₃NO₄^2-·C₇H₅NO₄·2.5H₂O, is a proton-transfer system obtained from pyridine-2,6-dicarboxylic acid and propane-1,3-diamine. Both neutral and dianionic forms of the diacid are observed in the crystal structure. The molecular structure contains also the diprotonated form of propane-1,3-diamine as well as water molecules. In the crystal structure, a wide range of hydrogen-bonding interactions connect the various fragments into a supramolecular structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005393/su6259sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005393/su6259Isup2.hkl Contains datablock I

CCDC reference: 284317

checkCIF report

Key indicators

Single-crystal X-ray study
T = 193 K
Mean (C-C) = 0.006 Å
R factor = 0.068
wR factor = 0.138
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT355_ALERT_3_A Long    O-H Bond (0.82A)   O1     -   H1O1   ...       1.28 Ang.

Author Response: the formation of the H-bond the distance between donor of proton atom and H atom is significantly elongated. In the case of extremely short H-bonds ( with O...O distance <2.500A) there is addition problem which is in part connected with the possible superposition of two different tautomers what in the some case can lead to pseudosymmetric H-bond or the long O-H distancses.

PLAT772_ALERT_2_A Suspect O-H Bond in CIF:      O5A    -H1OA    ..       1.42 Ang.


Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT213_ALERT_2_C Atom O3      has ADP max/min Ratio .............       3.70 prolat
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C7
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.40
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.25
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1A    -   H1OA   ...       1.07 Ang.

PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C15    -   C16    ...       1.43 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C13    -   C14    ...       1.53 Ang.
PLAT369_ALERT_2_C Long   C(sp2)-C(sp2) Bond  C8A    -   C9A    ...       1.53 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         28
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              C7 H3 N O4

   2 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  17 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   8 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: P3/PC (Siemens, 1989); cell refinement: P3/PC; data reduction: P3/PC; program(s) used to solve structure: SHELXTL-Plus (Sheldrick, 1998); program(s) used to refine structure: SHELXTL-Plus; molecular graphics: SHELXTL-Plus; software used to prepare material for publication: SHELXTL-Plus.

propane-1,3-diaminium–pyridine-2,6-dicarboxylate–pyridine-2,6-dicarboxylic acid—water (2/2/2/5) top

Crystal data top

C₃H₁₂N₂²⁺·C₇H₃NO₄²⁻·C₇H₅NO₄·2.5H₂O	Z = 4
M_r = 453.41	F(000) = 956
Triclinic, P1	D_x = 1.474 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8724 (16) Å	Cell parameters from 24 reflections
b = 13.534 (3) Å	θ = 9–12°
c = 20.986 (4) Å	µ = 0.12 mm⁻¹
α = 106.64 (3)°	T = 193 K
β = 90.54 (3)°	Prism, colorless
γ = 106.54 (3)°	0.30 × 0.25 × 0.20 mm
V = 2043.5 (7) Å³

Data collection top

Rebuild Syntex P2₁/Siemens P3 four-circle diffractometer	R_int = 0.074
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.2°
Graphite monochromator	h = 0→9
θ/2θ scans	k = −16→16
8323 measured reflections	l = −25→25
7768 independent reflections	2 standard reflections every 98 reflections
3755 reflections with I > 2σ(I)	intensity decay: 1.5%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: mixed
wR(F²) = 0.138	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0007P)² + 1.66P] where P = (F_o² + 2F_c²)/3
7768 reflections	(Δ/σ)_max = 0.001
572 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.31 e Å⁻³

Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1	0.3821 (4)	0.3459 (2)	0.10000 (17)	0.0252 (7)
N2	0.1746 (4)	−0.2737 (2)	−0.08494 (17)	0.0243 (7)
N3	0.6725 (4)	0.1512 (3)	0.93896 (18)	0.0304 (8)
H1N3	0.6829	0.0918	0.9487	0.037*
H2N3	0.5563	0.1411	0.9265	0.037*
H3N3	0.7116	0.2101	0.9757	0.037*
N4	1.2620 (4)	0.2951 (2)	0.95487 (17)	0.0256 (7)
H1N4	1.3222	0.3140	0.9959	0.031*
H2N4	1.2787	0.3548	0.9411	0.031*
H3N4	1.3032	0.2457	0.9252	0.031*
O1	0.3231 (4)	0.1398 (2)	0.02185 (15)	0.0354 (7)
H1O1	0.2689	0.0391	−0.0102	0.043*
O2	0.3843 (4)	0.0879 (2)	0.10882 (17)	0.0504 (9)
O3	0.3208 (5)	0.4923 (2)	0.05017 (17)	0.0643 (11)
H3O	0.3092	0.5210	0.0150	0.077*
O4	0.4117 (4)	0.6242 (2)	0.14469 (16)	0.0484 (9)
O5	0.2360 (4)	−0.0572 (2)	−0.03403 (16)	0.0475 (9)
O6	0.1356 (4)	−0.0496 (2)	−0.13196 (16)	0.0410 (8)
O7	0.2562 (4)	−0.3867 (2)	−0.00802 (14)	0.0348 (7)
O8	0.1973 (3)	−0.53586 (19)	−0.09530 (14)	0.0309 (7)
C1	0.3719 (5)	0.1571 (3)	0.0830 (2)	0.0308 (10)
C2	0.4145 (5)	0.2731 (3)	0.1269 (2)	0.0235 (8)
C3	0.4848 (5)	0.3002 (3)	0.1924 (2)	0.0270 (9)
H3A	0.5072	0.2465	0.2092	0.032*
C4	0.5226 (5)	0.4056 (3)	0.2336 (2)	0.0312 (9)
H4A	0.5714	0.4257	0.2786	0.037*
C5	0.4872 (5)	0.4802 (3)	0.2070 (2)	0.0287 (9)
H5A	0.5098	0.5531	0.2337	0.034*
C6	0.4189 (5)	0.4484 (3)	0.1413 (2)	0.0263 (9)
C7	0.3819 (5)	0.5296 (3)	0.1099 (2)	0.0259 (9)
C8	0.1660 (5)	−0.0988 (3)	−0.0935 (2)	0.0281 (9)
C9	0.1222 (5)	−0.2206 (3)	−0.1219 (2)	0.0249 (9)
C10	0.0280 (5)	−0.2717 (3)	−0.1841 (2)	0.0276 (9)
H10A	−0.0073	−0.2307	−0.2087	0.033*
C11	−0.0150 (5)	−0.3831 (3)	−0.2106 (2)	0.0354 (10)
H11A	−0.0799	−0.4201	−0.2532	0.042*
C12	0.0404 (5)	−0.4382 (3)	−0.1725 (2)	0.0322 (10)
H12A	0.0133	−0.5146	−0.1886	0.039*
C13	0.1349 (5)	−0.3820 (3)	−0.1113 (2)	0.0225 (8)
C14	0.1994 (5)	−0.4403 (3)	−0.0681 (2)	0.0294 (10)
C15	0.7796 (6)	0.1684 (5)	0.8842 (3)	0.0548 (14)
H15A	0.7276	0.1060	0.8441	0.066*
H15D	0.7648	0.2331	0.8746	0.066*
C16	0.9661 (6)	0.1824 (5)	0.8920 (3)	0.0597 (15)
H16A	1.0216	0.2161	0.8582	0.072*
H16D	0.9819	0.1095	0.8806	0.072*
C17	1.0710 (5)	0.2478 (4)	0.9588 (2)	0.0408 (11)
H17A	1.0200	0.3069	0.9800	0.049*
H17B	1.0571	0.2008	0.9881	0.049*
N1A	0.4602 (4)	0.8346 (2)	0.59569 (16)	0.0222 (7)
N2A	0.0451 (4)	0.2136 (2)	0.41211 (16)	0.0225 (7)
N3A	0.4737 (4)	0.2103 (2)	0.54707 (17)	0.0260 (7)
H1NA	0.5077	0.1864	0.5055	0.031*
H2NA	0.4440	0.1552	0.5655	0.031*
H3NA	0.5651	0.2655	0.5732	0.031*
N4A	0.0229 (4)	0.3461 (2)	0.55845 (18)	0.0301 (8)
H1NB	0.0016	0.2890	0.5206	0.036*
H2NB	0.1036	0.4046	0.5518	0.036*
H3NB	−0.0804	0.3617	0.5686	0.036*
O1A	0.3161 (3)	0.6283 (2)	0.51518 (14)	0.0337 (7)
H1OA	0.2844	0.5438	0.4902	0.040*
O2A	0.2209 (4)	0.5737 (2)	0.60294 (16)	0.0430 (8)
O3A	0.6727 (4)	0.9840 (2)	0.54874 (16)	0.0460 (8)
H3OA	0.7486	1.0368	0.5317	0.055*
O4A	0.6855 (4)	1.1163 (2)	0.64076 (16)	0.0469 (8)
O5A	0.2021 (4)	0.4310 (2)	0.45967 (16)	0.0415 (8)
O6A	0.3008 (4)	0.4337 (2)	0.36167 (17)	0.0457 (8)
O7A	−0.1450 (3)	0.1025 (2)	0.48986 (15)	0.0337 (7)
O8A	−0.2393 (3)	−0.0462 (2)	0.40231 (14)	0.0314 (7)
C1A	0.2923 (5)	0.6443 (3)	0.5779 (2)	0.0250 (9)
C2A	0.3598 (4)	0.7606 (3)	0.6223 (2)	0.0223 (8)
C3A	0.3168 (5)	0.7848 (3)	0.6870 (2)	0.0269 (9)
H3AA	0.2445	0.7295	0.7030	0.032*
C4A	0.3791 (5)	0.8899 (3)	0.7288 (2)	0.0301 (9)
H4AA	0.3497	0.9084	0.7736	0.036*
C5A	0.4866 (5)	0.9678 (3)	0.7030 (2)	0.0304 (10)
H5AA	0.5341	1.0406	0.7303	0.036*
C6A	0.5231 (5)	0.9373 (3)	0.6368 (2)	0.0230 (8)
C7A	0.6360 (5)	1.0209 (3)	0.6079 (2)	0.0281 (9)
C8A	0.2258 (5)	0.3868 (3)	0.4004 (2)	0.0257 (9)
C9A	0.1503 (5)	0.2640 (3)	0.3736 (2)	0.0234 (8)
C10A	0.1918 (5)	0.2123 (3)	0.3128 (2)	0.0246 (9)
H10B	0.2677	0.2521	0.2880	0.030*
C11A	0.1216 (5)	0.0998 (3)	0.2873 (2)	0.0305 (9)
H11B	0.1488	0.0615	0.2451	0.037*
C12A	0.0121 (5)	0.0468 (3)	0.3254 (2)	0.0281 (9)
H12B	−0.0392	−0.0294	0.3096	0.034*
C13A	−0.0230 (4)	0.1053 (3)	0.3868 (2)	0.0218 (8)
C14A	−0.1463 (5)	0.0481 (3)	0.4285 (2)	0.0254 (9)
C15A	0.3180 (5)	0.2492 (3)	0.5421 (2)	0.0276 (9)
H15B	0.2106	0.1862	0.5247	0.033*
H15C	0.3366	0.2914	0.5098	0.033*
C16A	0.2875 (5)	0.3190 (3)	0.6088 (2)	0.0334 (10)
H16B	0.3632	0.3943	0.6161	0.040*
H16C	0.3251	0.2934	0.6447	0.040*
C17A	0.0943 (5)	0.3182 (3)	0.6141 (2)	0.0329 (10)
H17C	0.0208	0.2455	0.6143	0.040*
H17D	0.0857	0.3706	0.6570	0.040*
O1W	0.1356 (4)	0.3133 (2)	0.77343 (17)	0.0466 (8)
H1W1	0.1567	0.3592	0.8183	0.056*
H2W1	0.0403	0.3156	0.7463	0.056*
O2W	0.7695 (4)	0.2990 (2)	0.74563 (15)	0.0397 (7)
H1W2	0.7456	0.3548	0.7802	0.048*
H2W2	0.6909	0.2334	0.7172	0.048*
O3W	0.3640 (3)	0.1343 (2)	0.85864 (14)	0.0314 (7)
H1W3	0.3517	0.1331	0.8133	0.038*
H2W3	0.2799	0.0686	0.8595	0.038*
O4W	0.3539 (4)	0.1811 (2)	0.73661 (15)	0.0384 (7)
H1W4	0.2757	0.2235	0.7506	0.046*
H2W4	0.2992	0.1413	0.6927	0.046*
O5W	0.7393 (3)	0.3771 (2)	0.63630 (15)	0.0319 (7)
H1W5	0.7586	0.3734	0.6802	0.038*
H2W5	0.7308	0.4484	0.6461	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0243 (17)	0.0210 (16)	0.035 (2)	0.0088 (13)	0.0022 (14)	0.0138 (15)
N2	0.0212 (16)	0.0224 (16)	0.035 (2)	0.0093 (13)	0.0082 (14)	0.0148 (15)
N3	0.0253 (18)	0.0282 (17)	0.041 (2)	0.0101 (14)	0.0014 (15)	0.0130 (16)
N4	0.0306 (17)	0.0151 (15)	0.031 (2)	0.0070 (13)	0.0015 (14)	0.0069 (14)
O1	0.0499 (18)	0.0209 (14)	0.038 (2)	0.0124 (13)	−0.0030 (14)	0.0104 (13)
O2	0.081 (2)	0.0269 (16)	0.051 (2)	0.0208 (16)	−0.0079 (18)	0.0194 (15)
O3	0.127 (3)	0.0234 (16)	0.045 (2)	0.0349 (19)	−0.032 (2)	0.0039 (15)
O4	0.079 (2)	0.0172 (15)	0.046 (2)	0.0137 (15)	−0.0018 (17)	0.0051 (14)
O5	0.073 (2)	0.0196 (14)	0.049 (2)	0.0149 (15)	−0.0153 (18)	0.0085 (14)
O6	0.0544 (19)	0.0272 (15)	0.047 (2)	0.0121 (14)	−0.0082 (15)	0.0199 (15)
O7	0.0558 (19)	0.0220 (14)	0.0294 (19)	0.0178 (13)	−0.0040 (14)	0.0061 (13)
O8	0.0424 (17)	0.0171 (13)	0.0353 (18)	0.0148 (12)	0.0016 (13)	0.0050 (12)
C1	0.036 (2)	0.025 (2)	0.040 (3)	0.0128 (18)	0.003 (2)	0.019 (2)
C2	0.024 (2)	0.0227 (19)	0.027 (2)	0.0073 (15)	0.0039 (17)	0.0114 (17)
C3	0.027 (2)	0.032 (2)	0.031 (3)	0.0131 (17)	0.0053 (18)	0.0183 (19)
C4	0.029 (2)	0.037 (2)	0.026 (3)	0.0068 (18)	−0.0011 (18)	0.0096 (19)
C5	0.025 (2)	0.0232 (19)	0.035 (3)	0.0041 (16)	0.0032 (18)	0.0077 (18)
C6	0.023 (2)	0.0199 (19)	0.035 (3)	0.0039 (16)	0.0048 (18)	0.0087 (18)
C7	0.028 (2)	0.021 (2)	0.027 (3)	0.0041 (16)	0.0009 (18)	0.0067 (18)
C8	0.029 (2)	0.025 (2)	0.030 (3)	0.0077 (17)	−0.0043 (18)	0.0088 (19)
C9	0.0196 (19)	0.0232 (19)	0.037 (3)	0.0057 (16)	0.0062 (17)	0.0176 (18)
C10	0.026 (2)	0.025 (2)	0.031 (3)	0.0063 (16)	−0.0047 (18)	0.0091 (18)
C11	0.035 (2)	0.028 (2)	0.038 (3)	0.0033 (18)	−0.007 (2)	0.009 (2)
C12	0.029 (2)	0.0191 (19)	0.052 (3)	0.0079 (17)	0.004 (2)	0.014 (2)
C13	0.0203 (19)	0.0176 (18)	0.033 (3)	0.0052 (15)	0.0029 (17)	0.0135 (17)
C14	0.030 (2)	0.020 (2)	0.040 (3)	0.0071 (16)	0.0049 (19)	0.0132 (19)
C15	0.033 (3)	0.076 (4)	0.051 (4)	0.012 (2)	0.009 (2)	0.017 (3)
C16	0.032 (3)	0.087 (4)	0.039 (3)	0.002 (3)	0.002 (2)	0.003 (3)
C17	0.028 (2)	0.055 (3)	0.045 (3)	0.011 (2)	0.014 (2)	0.024 (2)
N1A	0.0164 (16)	0.0178 (15)	0.034 (2)	0.0046 (12)	0.0070 (13)	0.0109 (14)
N2A	0.0186 (16)	0.0228 (16)	0.028 (2)	0.0062 (13)	0.0032 (13)	0.0105 (15)
N3A	0.0243 (17)	0.0220 (16)	0.034 (2)	0.0076 (13)	0.0066 (14)	0.0105 (15)
N4A	0.0229 (17)	0.0247 (17)	0.048 (2)	0.0091 (14)	0.0057 (15)	0.0176 (16)
O1A	0.0419 (17)	0.0214 (14)	0.0336 (19)	0.0008 (12)	0.0074 (13)	0.0104 (13)
O2A	0.0506 (19)	0.0267 (15)	0.047 (2)	−0.0016 (13)	0.0094 (15)	0.0170 (15)
O3A	0.061 (2)	0.0185 (14)	0.045 (2)	−0.0067 (13)	0.0215 (16)	0.0073 (14)
O4A	0.057 (2)	0.0217 (16)	0.050 (2)	0.0019 (14)	0.0201 (16)	0.0015 (15)
O5A	0.0546 (19)	0.0222 (15)	0.041 (2)	−0.0031 (13)	0.0094 (15)	0.0131 (14)
O6A	0.060 (2)	0.0251 (15)	0.058 (2)	0.0105 (14)	0.0298 (17)	0.0221 (16)
O7A	0.0327 (16)	0.0231 (14)	0.037 (2)	−0.0064 (12)	0.0032 (13)	0.0115 (13)
O8A	0.0326 (15)	0.0212 (14)	0.0334 (18)	−0.0040 (12)	−0.0021 (13)	0.0095 (13)
C1A	0.028 (2)	0.024 (2)	0.027 (3)	0.0069 (16)	0.0050 (17)	0.0136 (18)
C2A	0.0184 (19)	0.0240 (19)	0.032 (2)	0.0115 (16)	0.0052 (16)	0.0145 (18)
C3A	0.026 (2)	0.031 (2)	0.029 (3)	0.0107 (17)	0.0055 (17)	0.0153 (19)
C4A	0.039 (2)	0.026 (2)	0.027 (3)	0.0158 (18)	0.0069 (19)	0.0060 (18)
C5A	0.029 (2)	0.024 (2)	0.041 (3)	0.0109 (17)	0.0059 (19)	0.0108 (19)
C6A	0.0187 (19)	0.0240 (19)	0.031 (2)	0.0096 (15)	0.0026 (16)	0.0124 (18)
C7A	0.025 (2)	0.018 (2)	0.040 (3)	0.0060 (16)	0.0053 (19)	0.0081 (19)
C8A	0.024 (2)	0.0187 (19)	0.033 (3)	0.0045 (16)	0.0048 (18)	0.0070 (18)
C9A	0.021 (2)	0.0214 (18)	0.027 (2)	0.0042 (15)	0.0003 (16)	0.0081 (17)
C10A	0.024 (2)	0.026 (2)	0.028 (2)	0.0084 (16)	0.0041 (17)	0.0131 (18)
C11A	0.029 (2)	0.027 (2)	0.032 (3)	0.0075 (17)	0.0008 (18)	0.0060 (19)
C12A	0.029 (2)	0.0194 (18)	0.031 (3)	0.0024 (16)	0.0033 (18)	0.0040 (18)
C13A	0.0155 (18)	0.0184 (18)	0.027 (2)	0.0009 (14)	−0.0078 (16)	0.0051 (16)
C14A	0.025 (2)	0.020 (2)	0.027 (3)	0.0007 (16)	−0.0054 (17)	0.0084 (18)
C15A	0.024 (2)	0.026 (2)	0.035 (3)	0.0109 (16)	0.0012 (17)	0.0101 (18)
C16A	0.026 (2)	0.033 (2)	0.043 (3)	0.0113 (18)	0.0010 (19)	0.012 (2)
C17A	0.030 (2)	0.035 (2)	0.036 (3)	0.0093 (18)	0.0063 (19)	0.013 (2)
O1W	0.0454 (19)	0.0418 (18)	0.053 (2)	0.0237 (15)	−0.0047 (16)	0.0042 (16)
O2W	0.0406 (17)	0.0269 (15)	0.042 (2)	0.0060 (13)	−0.0042 (14)	−0.0002 (13)
O3W	0.0286 (15)	0.0316 (15)	0.0353 (18)	0.0103 (12)	0.0031 (12)	0.0105 (13)
O4W	0.0364 (17)	0.0278 (15)	0.047 (2)	0.0114 (13)	−0.0049 (14)	0.0038 (14)
O5W	0.0275 (14)	0.0243 (14)	0.0423 (19)	0.0066 (11)	0.0004 (13)	0.0085 (13)

Geometric parameters (Å, º) top

N1—C2	1.348 (4)	N3A—H1NA	0.9100
N1—C6	1.356 (5)	N3A—H2NA	0.9100
N2—C9	1.330 (4)	N3A—H3NA	0.9100
N2—C13	1.351 (5)	N4A—C17A	1.478 (5)
N3—C15	1.465 (6)	N4A—H1NB	0.9100
N3—H1N3	0.9100	N4A—H2NB	0.9100
N3—H2N3	0.9100	N4A—H3NB	0.9100
N3—H3N3	0.9100	O1A—C1A	1.296 (5)
N4—C17	1.470 (5)	O1A—H1OA	1.0655
N4—H1N4	0.9100	O2A—C1A	1.222 (4)
N4—H2N4	0.9100	O3A—C7A	1.269 (5)
N4—H3N4	0.9100	O3A—H3OA	0.9500
O1—C1	1.273 (5)	O4A—C7A	1.222 (5)
O1—H1O1	1.2775	O5A—C8A	1.258 (5)
O2—C1	1.233 (4)	O5A—H1OA	1.4247
O3—C7	1.243 (5)	O6A—C8A	1.226 (5)
O3—H3O	0.9416	O7A—C14A	1.286 (5)
O4—C7	1.232 (5)	O8A—C14A	1.236 (4)
O5—C8	1.260 (5)	C1A—C2A	1.518 (5)
O5—H1O1	1.2028	C2A—C3A	1.371 (5)
O6—C8	1.244 (4)	C3A—C4A	1.383 (6)
O7—C14	1.263 (5)	C3A—H3AA	0.9500
O8—C14	1.251 (4)	C4A—C5A	1.396 (5)
C1—C2	1.514 (5)	C4A—H4AA	0.9500
C2—C3	1.382 (5)	C5A—C6A	1.390 (6)
C3—C4	1.385 (6)	C5A—H5AA	0.9500
C3—H3A	0.9500	C6A—C7A	1.505 (5)
C4—C5	1.374 (5)	C8A—C9A	1.525 (5)
C4—H4A	0.9500	C9A—C10A	1.361 (5)
C5—C6	1.374 (6)	C10A—C11A	1.399 (5)
C5—H5A	0.9500	C10A—H10B	0.9500
C6—C7	1.522 (5)	C11A—C12A	1.374 (5)
C8—C9	1.516 (5)	C11A—H11B	0.9500
C9—C10	1.380 (5)	C12A—C13A	1.383 (5)
C10—C11	1.387 (5)	C12A—H12B	0.9500
C10—H10A	0.9500	C13A—C14A	1.511 (5)
C11—C12	1.379 (5)	C15A—C16A	1.514 (6)
C11—H11A	0.9500	C15A—H15B	0.9900
C12—C13	1.373 (6)	C15A—H15C	0.9900
C12—H12A	0.9500	C16A—C17A	1.523 (5)
C13—C14	1.527 (5)	C16A—H16B	0.9900
C15—C16	1.427 (6)	C16A—H16C	0.9900
C15—H15A	0.9900	C17A—H17C	0.9900
C15—H15D	0.9900	C17A—H17D	0.9900
C16—C17	1.511 (6)	O1W—H1W1	0.9500
C16—H16A	0.9900	O1W—H2W1	0.9504
C16—H16D	0.9900	O2W—H1W2	0.9499
C17—H17A	0.9900	O2W—H2W2	0.9501
C17—H17B	0.9900	O3W—H1W3	0.9500
N1A—C2A	1.348 (4)	O3W—H2W3	0.9501
N1A—C6A	1.354 (5)	O4W—H1W4	0.9502
N2A—C9A	1.346 (5)	O4W—H2W4	0.9500
N2A—C13A	1.348 (4)	O5W—H1W5	0.9500
N3A—C15A	1.478 (4)	O5W—H2W5	0.9500

C2—N1—C6	116.2 (3)	C15A—N3A—H2NA	109.5
C9—N2—C13	117.2 (3)	H1NA—N3A—H2NA	109.5
C15—N3—H1N3	109.5	C15A—N3A—H3NA	109.5
C15—N3—H2N3	109.5	H1NA—N3A—H3NA	109.5
H1N3—N3—H2N3	109.5	H2NA—N3A—H3NA	109.5
C15—N3—H3N3	109.5	C17A—N4A—H1NB	109.5
H1N3—N3—H3N3	109.5	C17A—N4A—H2NB	109.5
H2N3—N3—H3N3	109.5	H1NB—N4A—H2NB	109.5
C17—N4—H1N4	109.5	C17A—N4A—H3NB	109.5
C17—N4—H2N4	109.5	H1NB—N4A—H3NB	109.5
H1N4—N4—H2N4	109.5	H2NB—N4A—H3NB	109.5
C17—N4—H3N4	109.5	C1A—O1A—H1OA	110.0
H1N4—N4—H3N4	109.5	C7A—O3A—H3OA	114.4
H2N4—N4—H3N4	109.5	C8A—O5A—H1OA	120.2
C1—O1—H1O1	112.2	O2A—C1A—O1A	125.0 (4)
C7—O3—H3O	136.0	O2A—C1A—C2A	118.9 (4)
C8—O5—H1O1	117.7	O1A—C1A—C2A	116.0 (3)
O2—C1—O1	125.7 (4)	N1A—C2A—C3A	123.6 (4)
O2—C1—C2	118.6 (4)	N1A—C2A—C1A	117.7 (4)
O1—C1—C2	115.8 (3)	C3A—C2A—C1A	118.7 (3)
N1—C2—C3	122.7 (3)	C2A—C3A—C4A	119.9 (4)
N1—C2—C1	118.0 (3)	C2A—C3A—H3AA	120.1
C3—C2—C1	119.2 (3)	C4A—C3A—H3AA	120.1
C2—C3—C4	120.1 (4)	C3A—C4A—C5A	117.8 (4)
C2—C3—H3A	120.0	C3A—C4A—H4AA	121.1
C4—C3—H3A	120.0	C5A—C4A—H4AA	121.1
C5—C4—C3	117.7 (4)	C6A—C5A—C4A	119.0 (4)
C5—C4—H4A	121.1	C6A—C5A—H5AA	120.5
C3—C4—H4A	121.1	C4A—C5A—H5AA	120.5
C4—C5—C6	119.5 (4)	N1A—C6A—C5A	123.1 (3)
C4—C5—H5A	120.3	N1A—C6A—C7A	117.3 (4)
C6—C5—H5A	120.3	C5A—C6A—C7A	119.6 (3)
N1—C6—C5	123.8 (4)	O4A—C7A—O3A	124.5 (4)
N1—C6—C7	115.4 (4)	O4A—C7A—C6A	120.6 (4)
C5—C6—C7	120.8 (3)	O3A—C7A—C6A	114.9 (3)
O4—C7—O3	125.7 (4)	O6A—C8A—O5A	125.8 (4)
O4—C7—C6	118.8 (4)	O6A—C8A—C9A	117.0 (4)
O3—C7—C6	115.5 (3)	O5A—C8A—C9A	117.2 (3)
O6—C8—O5	126.4 (4)	N2A—C9A—C10A	124.0 (3)
O6—C8—C9	116.9 (4)	N2A—C9A—C8A	117.3 (4)
O5—C8—C9	116.6 (3)	C10A—C9A—C8A	118.7 (3)
N2—C9—C10	122.8 (3)	C9A—C10A—C11A	119.3 (4)
N2—C9—C8	118.2 (4)	C9A—C10A—H10B	120.3
C10—C9—C8	119.0 (3)	C11A—C10A—H10B	120.3
C9—C10—C11	119.9 (4)	C12A—C11A—C10A	117.6 (4)
C9—C10—H10A	120.1	C12A—C11A—H11B	121.2
C11—C10—H10A	120.1	C10A—C11A—H11B	121.2
C12—C11—C10	117.3 (4)	C11A—C12A—C13A	119.5 (4)
C12—C11—H11A	121.3	C11A—C12A—H12B	120.2
C10—C11—H11A	121.3	C13A—C12A—H12B	120.2
C13—C12—C11	119.7 (4)	N2A—C13A—C12A	123.3 (3)
C13—C12—H12A	120.1	N2A—C13A—C14A	116.7 (4)
C11—C12—H12A	120.1	C12A—C13A—C14A	119.9 (3)
N2—C13—C12	123.0 (3)	O8A—C14A—O7A	124.6 (4)
N2—C13—C14	115.9 (3)	O8A—C14A—C13A	119.0 (4)
C12—C13—C14	121.1 (3)	O7A—C14A—C13A	116.4 (3)
O8—C14—O7	125.2 (4)	N3A—C15A—C16A	112.1 (3)
O8—C14—C13	117.6 (4)	N3A—C15A—H15B	109.2
O7—C14—C13	117.2 (3)	C16A—C15A—H15B	109.2
C16—C15—N3	119.2 (4)	N3A—C15A—H15C	109.2
C16—C15—H15A	107.5	C16A—C15A—H15C	109.2
N3—C15—H15A	107.5	H15B—C15A—H15C	107.9
C16—C15—H15D	107.5	C15A—C16A—C17A	113.4 (3)
N3—C15—H15D	107.5	C15A—C16A—H16B	108.9
H15A—C15—H15D	107.0	C17A—C16A—H16B	108.9
C15—C16—C17	119.3 (4)	C15A—C16A—H16C	108.9
C15—C16—H16A	107.5	C17A—C16A—H16C	108.9
C17—C16—H16A	107.5	H16B—C16A—H16C	107.7
C15—C16—H16D	107.5	N4A—C17A—C16A	112.2 (3)
C17—C16—H16D	107.5	N4A—C17A—H17C	109.2
H16A—C16—H16D	107.0	C16A—C17A—H17C	109.2
N4—C17—C16	114.1 (4)	N4A—C17A—H17D	109.2
N4—C17—H17A	108.7	C16A—C17A—H17D	109.2
C16—C17—H17A	108.7	H17C—C17A—H17D	107.9
N4—C17—H17B	108.7	H1W1—O1W—H2W1	116.9
C16—C17—H17B	108.7	H1W2—O2W—H2W2	130.4
H17A—C17—H17B	107.6	H1W3—O3W—H2W3	103.7
C2A—N1A—C6A	116.6 (3)	H1W4—O4W—H2W4	99.3
C9A—N2A—C13A	116.2 (3)	H1W5—O5W—H2W5	100.4
C15A—N3A—H1NA	109.5

C6—N1—C2—C3	−1.3 (5)	C6A—N1A—C2A—C3A	1.4 (5)
C6—N1—C2—C1	178.8 (3)	C6A—N1A—C2A—C1A	−178.2 (3)
O2—C1—C2—N1	−173.0 (4)	O2A—C1A—C2A—N1A	170.7 (3)
O1—C1—C2—N1	6.1 (5)	O1A—C1A—C2A—N1A	−9.4 (5)
O2—C1—C2—C3	7.2 (6)	O2A—C1A—C2A—C3A	−8.9 (5)
O1—C1—C2—C3	−173.8 (3)	O1A—C1A—C2A—C3A	171.1 (3)
N1—C2—C3—C4	0.9 (6)	N1A—C2A—C3A—C4A	−0.6 (6)
C1—C2—C3—C4	−179.2 (4)	C1A—C2A—C3A—C4A	178.9 (3)
C2—C3—C4—C5	0.3 (6)	C2A—C3A—C4A—C5A	−0.7 (5)
C3—C4—C5—C6	−0.9 (6)	C3A—C4A—C5A—C6A	1.2 (5)
C2—N1—C6—C5	0.7 (5)	C2A—N1A—C6A—C5A	−0.8 (5)
C2—N1—C6—C7	179.8 (3)	C2A—N1A—C6A—C7A	179.8 (3)
C4—C5—C6—N1	0.4 (6)	C4A—C5A—C6A—N1A	−0.5 (6)
C4—C5—C6—C7	−178.7 (3)	C4A—C5A—C6A—C7A	178.9 (3)
N1—C6—C7—O4	179.7 (4)	N1A—C6A—C7A—O4A	174.4 (4)
C5—C6—C7—O4	−1.1 (6)	C5A—C6A—C7A—O4A	−5.0 (6)
N1—C6—C7—O3	0.6 (5)	N1A—C6A—C7A—O3A	−5.5 (5)
C5—C6—C7—O3	179.8 (4)	C5A—C6A—C7A—O3A	175.1 (4)
C13—N2—C9—C10	1.2 (5)	C13A—N2A—C9A—C10A	−1.0 (5)
C13—N2—C9—C8	−179.7 (3)	C13A—N2A—C9A—C8A	178.7 (3)
O6—C8—C9—N2	171.3 (3)	O6A—C8A—C9A—N2A	−170.2 (3)
O5—C8—C9—N2	−6.1 (5)	O5A—C8A—C9A—N2A	8.2 (5)
O6—C8—C9—C10	−9.6 (6)	O6A—C8A—C9A—C10A	9.5 (5)
O5—C8—C9—C10	173.1 (4)	O5A—C8A—C9A—C10A	−172.1 (3)
N2—C9—C10—C11	−0.3 (6)	N2A—C9A—C10A—C11A	0.5 (6)
C8—C9—C10—C11	−179.3 (4)	C8A—C9A—C10A—C11A	−179.2 (3)
C9—C10—C11—C12	−0.2 (6)	C9A—C10A—C11A—C12A	0.3 (6)
C10—C11—C12—C13	−0.4 (6)	C10A—C11A—C12A—C13A	−0.6 (5)
C9—N2—C13—C12	−1.8 (5)	C9A—N2A—C13A—C12A	0.7 (5)
C9—N2—C13—C14	179.2 (3)	C9A—N2A—C13A—C14A	−178.0 (3)
C11—C12—C13—N2	1.4 (6)	C11A—C12A—C13A—N2A	0.1 (6)
C11—C12—C13—C14	−179.6 (4)	C11A—C12A—C13A—C14A	178.7 (3)
N2—C13—C14—O8	−166.1 (3)	N2A—C13A—C14A—O8A	165.6 (3)
C12—C13—C14—O8	14.9 (6)	C12A—C13A—C14A—O8A	−13.1 (5)
N2—C13—C14—O7	11.6 (5)	N2A—C13A—C14A—O7A	−15.0 (5)
C12—C13—C14—O7	−167.4 (4)	C12A—C13A—C14A—O7A	166.3 (3)
N3—C15—C16—C17	−39.1 (8)	N3A—C15A—C16A—C17A	−153.7 (3)
C15—C16—C17—N4	−155.5 (5)	C15A—C16A—C17A—N4A	−53.4 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H1N3···O5ⁱ	0.91	2.11	2.841 (4)	136
N3—H1N3···O2ⁱ	0.91	2.29	2.997 (4)	135
N3—H2N3···O3W	0.91	2.03	2.859 (4)	150
N3—H3N3···O7ⁱ	0.91	2.23	2.982 (4)	140
N3—H3N3···N2ⁱ	0.91	2.28	3.077 (4)	146
N4—H1N4···N1ⁱⁱ	0.91	2.12	3.003 (4)	162
N4—H2N4···O8ⁱⁱⁱ	0.91	2.09	2.938 (4)	155
N4—H3N4···O3W^iv	0.91	1.92	2.823 (4)	174
O3—H3O···O7^v	0.94	1.61	2.457 (4)	147
O3—H3O···O7^v	0.94	1.61	2.457 (4)	147
O3—H3O···O8^v	0.94	2.30	3.078 (4)	140
O5—H1O1···O1	1.20	1.28	2.471 (4)	170
N3A—H1NA···N1A^vi	0.91	2.09	2.963 (4)	161
N3A—H1NA···O3A^vi	0.91	2.29	2.737 (4)	110
N3A—H2NA···O8A^vii	0.91	2.11	2.919 (4)	147
N3A—H3NA···O5W	0.91	1.89	2.791 (4)	173
N4A—H1NB···N2A	0.91	2.29	3.116 (4)	152
N4A—H1NB···O7A	0.91	2.35	3.074 (4)	137
N4A—H2NB···O2A	0.91	2.15	2.895 (4)	139
N4A—H2NB···O5A	0.91	2.18	2.847 (4)	130
N4A—H3NB···O5W^viii	0.91	2.03	2.836 (4)	147
O1A—H1OA···O5A	1.07	1.43	2.475 (4)	167
O3A—H3OA···O7A^ix	0.95	1.52	2.453 (4)	167
O1W—H1W1···O8^x	0.95	1.91	2.861 (4)	174
O1W—H2W1···O2W^viii	0.95	2.08	2.876 (4)	140
O2W—H1W2···O4^vi	0.95	2.02	2.820 (4)	141
O2W—H2W2···O4A^xi	0.95	1.90	2.705 (4)	142
O3W—H1W3···O4W	0.95	1.90	2.814 (4)	161
O3W—H2W3···O6^xii	0.95	1.74	2.684 (4)	175
O4W—H1W4···O1W	0.95	1.83	2.781 (4)	175
O4W—H2W4···O8A^vii	0.95	2.01	2.934 (4)	166
O5W—H1W5···O2W	0.95	1.94	2.821 (4)	154
O5W—H2W5···O6A^vi	0.95	1.73	2.656 (4)	163

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x+1, y, z+1; (iii) x+1, y+1, z+1; (iv) x+1, y, z; (v) x, y+1, z; (vi) −x+1, −y+1, −z+1; (vii) −x, −y, −z+1; (viii) x−1, y, z; (ix) x+1, y+1, z; (x) x, y+1, z+1; (xi) x, y−1, z; (xii) x, y, z+1.

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A proton transfer compound: propane-1,3-di­aminium-pyridine-2,6-dicarboxyl­ate-pyridine-2,6-dicarboxylic acid-water (2/2/2/5)

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A proton transfer compound: propane-1,3-diaminium-pyridine-2,6-dicarboxylate-pyridine-2,6-dicarboxylic acid-water (2/2/2/5)