Hydrogen bonding in 2,2′,2′′-(nitrilo­trimethyl­ene)tripyridinium hydrogenphosphate tetra­kis(perchlorate) dihydrate and related compounds

Hazell, A.

doi:10.1107/S160053680605080X

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Hydrogen bonding in 2,2',2''-(nitrilotrimethylene)tripyridinium hydrogenphosphate tetrakis(perchlorate) dihydrate and related compounds

A. Hazell

In the title salt, 2C₁₈H₂₁N₄³⁺·HPO₄^2-.4 ClO₄^-·2H₂O. the protons of each of the pyridyl N atoms are hydrogen bonded to one HPO₄^2- ion. In one 2,2',2''-(nitrilotrimethylene)tripyridinium cation, all three pyridine N atoms are hydrogen bonded to the same oxygen and the ligand has approximate threefold symmetry; in the other, there are two hydrogen bonds to one O atom, and only one to the third O atom, resulting in an asymmetric ligand. The hydrogen-bonding modes observed in this and related compounds are discussed and their geometries compared.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605080X/jh2046sup1.cif Contains datablocks fos, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680605080X/jh2046Isup2.hkl Contains datablock I

CCDC reference: 630036

checkCIF report

Key indicators

Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.004 Å
R factor = 0.053
wR factor = 0.051
Data-to-parameter ratio = 14.0

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR') is < 0.90
            Tmin and Tmax reported:      0.692     0.953
            Tmin(prime) and Tmax expected:      0.847     0.950
            RR(prime) =      0.814
            Please check that your absorption correction is appropriate.
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large .............       0.81
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.59 Ratio
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl1
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl2
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl3
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors for        Cl4
PLAT354_ALERT_3_C Short   O-H Bond (0.82A)   O1     -   HO1    ...       0.69 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O18    ..  C36     ..       3.00 Ang.
PLAT432_ALERT_2_C Short Inter X...Y Contact  O19    ..  C62     ..       2.97 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      38.00 A   3 
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         11
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C18 H21 N4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          4
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          5
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          7
              Cl O4
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          8
              H2 O
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          9
              H2 O

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

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

Computing details top

Data collection: SMART (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999) and KRYSTAL (Hazell, 1995); program(s) used to refine structure: modified ORFLS (Busing et al., 1962) and KRYSTAL; molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and KRYSTAL; software used to prepare material for publication: KRYSTAL.

bis[2,2',2''-(nitrilotrimethylene)tripyridinium] hydrogenphosphate tetrakis(perchlorate) dihydrate top

Crystal data top

2C₁₈H₂₁N₄³⁺·HO₄P²⁻·4ClO₄⁻·2H₂O	F(000) = 2312.0
M_r = 1116.64	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8192 reflections
a = 16.1366 (7) Å	θ = 2.0–29.8°
b = 12.8104 (6) Å	µ = 0.37 mm⁻¹
c = 23.832 (1) Å	T = 120 K
β = 100.988 (1)°	Plate, colourless
V = 4836.1 (4) Å³	0.44 × 0.44 × 0.14 mm
Z = 4

Data collection top

Siemens SMART CCD diffractometer	13850 independent reflections
Radiation source: x-ray tube	9018 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.031
ω rotation scans with narrow frames	θ_max = 29.8°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
T_min = 0.692, T_max = 0.953	k = −15→18
45366 measured reflections	l = −33→32

Refinement top

Refinement on F	0 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.053	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.051	w = 1/{[σ_cs(F²) + B + (1 + A)F²]^1/2- \|F\|}², with A = 0.03, B = 0.5
S = 1.04	(Δ/σ)_max = 0.001
9018 reflections	Δρ_max = 0.81 (8) e Å⁻³
644 parameters	Δρ_min = −1.12 (8) e Å⁻³

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

	x	y	z	U_iso*/U_eq
Cl1	0.04627 (5)	−0.35651 (6)	0.65619 (4)	0.0331 (4)
Cl2	0.32818 (5)	−0.25605 (7)	0.42885 (3)	0.0312 (4)
Cl3	0.23618 (5)	0.25594 (6)	0.57717 (3)	0.0257 (4)
Cl4	0.55280 (4)	−0.22233 (6)	0.70648 (3)	0.0248 (4)
P1	0.20718 (5)	−0.05652 (6)	0.74201 (3)	0.0198 (4)
O1	0.1496 (2)	−0.1491 (2)	0.7567 (1)	0.039 (2)
O2	0.1589 (1)	0.0060 (2)	0.6919 (1)	0.031 (1)
O3	0.2886 (1)	−0.1021 (2)	0.7295 (1)	0.024 (1)
O4	0.2227 (1)	0.0084 (2)	0.7968 (1)	0.021 (1)
O5	−0.0228 (2)	−0.3735 (4)	0.6821 (1)	0.091 (3)
O6	0.1103 (2)	−0.4195 (4)	0.6822 (2)	0.134 (4)
O7	0.0782 (3)	−0.2541 (3)	0.6629 (2)	0.130 (4)
O8	0.0213 (2)	−0.3710 (3)	0.5964 (1)	0.074 (2)
O9	0.2426 (2)	−0.2668 (3)	0.4353 (2)	0.075 (2)
O10	0.3332 (3)	−0.2651 (3)	0.3714 (1)	0.094 (3)
O11	0.3565 (2)	−0.1563 (2)	0.4513 (1)	0.071 (2)
O12	0.3751 (2)	−0.3380 (3)	0.4603 (1)	0.084 (3)
O13	0.2384 (3)	0.2303 (4)	0.6342 (1)	0.118 (4)
O14	0.2325 (2)	0.1649 (2)	0.5435 (1)	0.059 (2)
O15	0.1645 (2)	0.3200 (2)	0.5549 (1)	0.061 (2)
O16	0.3110 (2)	0.3134 (2)	0.5734 (1)	0.054 (2)
O17	0.4995 (1)	−0.3109 (2)	0.6908 (1)	0.038 (1)
O18	0.5562 (2)	−0.1587 (2)	0.6576 (1)	0.047 (2)
O19	0.6366 (1)	−0.2576 (3)	0.7296 (1)	0.064 (2)
O20	0.5198 (2)	−0.1626 (2)	0.7474 (1)	0.072 (2)
O21	0.1332 (2)	−0.1013 (3)	0.3816 (2)	0.076 (2)
O22	−0.0148 (2)	−0.1242 (3)	0.3030 (2)	0.091 (3)
N1	0.2676 (1)	−0.1724 (2)	0.5980 (1)	0.018 (1)
N2	0.2558 (1)	0.1265 (2)	0.9064 (1)	0.020 (1)
N11	0.0938 (1)	−0.0688 (2)	0.5929 (1)	0.022 (1)
N21	0.2944 (1)	−0.2979 (2)	0.6949 (1)	0.022 (1)
N31	0.3749 (2)	−0.0120 (2)	0.6582 (1)	0.025 (1)
N41	0.1404 (1)	−0.0470 (2)	0.8821 (1)	0.022 (1)
N51	0.3819 (1)	0.0229 (2)	0.8593 (1)	0.020 (1)
N61	0.1880 (2)	0.2132 (2)	0.8000 (1)	0.025 (1)
C12	0.0103 (2)	−0.0650 (2)	0.5913 (1)	0.026 (2)
C13	−0.0463 (2)	−0.1020 (3)	0.5448 (1)	0.028 (2)
C14	−0.0150 (2)	−0.1443 (2)	0.4996 (1)	0.028 (2)
C15	0.0710 (2)	−0.1477 (2)	0.5022 (1)	0.025 (2)
C16	0.1255 (2)	−0.1090 (2)	0.5495 (1)	0.019 (1)
C17	0.2190 (2)	−0.1063 (2)	0.5523 (1)	0.021 (1)
C22	0.3231 (2)	−0.3490 (3)	0.7440 (1)	0.027 (2)
C23	0.3355 (2)	−0.4552 (3)	0.7437 (1)	0.031 (2)
C24	0.3168 (2)	−0.5077 (2)	0.6919 (1)	0.030 (2)
C25	0.2879 (2)	−0.4529 (2)	0.6421 (1)	0.025 (2)
C26	0.2768 (2)	−0.3461 (2)	0.6439 (1)	0.021 (1)
C27	0.2423 (2)	−0.2822 (2)	0.5914 (1)	0.023 (1)
C32	0.4055 (2)	0.0810 (3)	0.6771 (2)	0.039 (2)
C33	0.4556 (2)	0.1358 (3)	0.6477 (2)	0.049 (2)
C34	0.4716 (2)	0.0954 (3)	0.5973 (2)	0.048 (3)
C35	0.4388 (2)	−0.0008 (3)	0.5784 (2)	0.037 (2)
C36	0.3909 (2)	−0.0557 (2)	0.6102 (1)	0.024 (2)
C37	0.3581 (2)	−0.1632 (2)	0.5956 (1)	0.022 (1)
C42	0.0720 (2)	−0.1073 (2)	0.8657 (1)	0.027 (2)
C43	0.0223 (2)	−0.1349 (2)	0.9044 (1)	0.028 (2)
C44	0.0444 (2)	−0.0985 (2)	0.9599 (1)	0.027 (2)
C45	0.1149 (2)	−0.0363 (2)	0.9754 (1)	0.025 (2)
C46	0.1640 (2)	−0.0108 (2)	0.9356 (1)	0.022 (1)
C47	0.2445 (2)	0.0500 (3)	0.9504 (1)	0.025 (2)
C52	0.4343 (2)	−0.0471 (2)	0.8428 (1)	0.024 (2)
C53	0.5150 (2)	−0.0582 (3)	0.8738 (1)	0.028 (2)
C54	0.5399 (2)	0.0042 (3)	0.9213 (1)	0.032 (2)
C55	0.4853 (2)	0.0765 (3)	0.9367 (1)	0.027 (2)
C56	0.4048 (2)	0.0857 (2)	0.9048 (1)	0.022 (1)
C57	0.3427 (2)	0.1657 (2)	0.9167 (1)	0.026 (2)
C62	0.1763 (2)	0.2540 (3)	0.7471 (1)	0.030 (2)
C63	0.1606 (2)	0.3586 (3)	0.7392 (1)	0.037 (2)
C64	0.1605 (2)	0.4206 (3)	0.7865 (2)	0.038 (2)
C65	0.1750 (2)	0.3766 (3)	0.8408 (1)	0.034 (2)
C66	0.1873 (2)	0.2710 (2)	0.8472 (1)	0.026 (2)
C67	0.1967 (2)	0.2141 (2)	0.9033 (1)	0.026 (2)
HO1	0.124 (3)	−0.174 (3)	0.734 (2)	0.05 (1)*
HO21a	0.0873	−0.1194	0.3510	0.150*
HO21b	0.1708	−0.1598	0.3820	0.150*
HO22a	−0.0656	−0.0874	0.3059	0.150*
HO22b	−0.0064	−0.1296	0.2643	0.150*
HN11	0.1313	−0.0424	0.6254	0.026*
HN21	0.2862	−0.2246	0.6963	0.026*
HN31	0.3404	−0.0488	0.6796	0.029*
HN41	0.1735	−0.0291	0.8545	0.027*
HN51	0.3261	0.0284	0.8377	0.024*
HN61	0.1973	0.1402	0.8044	0.030*
H12	−0.0101	−0.0364	0.6228	0.032*
H13	−0.1054	−0.0985	0.5438	0.034*
H14	−0.0525	−0.1709	0.4671	0.034*
H15	0.0929	−0.1767	0.4713	0.030*
H17a	0.2302	−0.1296	0.5166	0.025*
H17b	0.2376	−0.0362	0.5587	0.025*
H22	0.3349	−0.3116	0.7791	0.033*
H23	0.3565	−0.4918	0.7781	0.037*
H24	0.3237	−0.5813	0.6907	0.036*
H25	0.2758	−0.4886	0.6065	0.030*
H27a	0.2628	−0.3105	0.5598	0.027*
H27b	0.1825	−0.2860	0.5843	0.027*
H32	0.3923	0.1091	0.7112	0.046*
H33	0.4791	0.2009	0.6617	0.059*
H34	0.5051	0.1334	0.5756	0.058*
H35	0.4493	−0.0289	0.5436	0.044*
H37a	0.3657	−0.1799	0.5581	0.026*
H37b	0.3891	−0.2110	0.6221	0.026*
H42	0.0579	−0.1311	0.8273	0.032*
H43	−0.0260	−0.1779	0.8932	0.034*
H44	0.0111	−0.1163	0.9874	0.032*
H45	0.1297	−0.0108	1.0135	0.031*
H47a	0.2447	0.0862	0.9852	0.030*
H47b	0.2904	0.0023	0.9553	0.030*
H52	0.4157	−0.0890	0.8099	0.029*
H53	0.5527	−0.1077	0.8627	0.034*
H54	0.5952	−0.0027	0.9434	0.038*
H55	0.5029	0.1198	0.9692	0.033*
H57a	0.3578	0.1865	0.9556	0.031*
H57b	0.3453	0.2243	0.8926	0.031*
H62	0.1789	0.2103	0.7153	0.036*
H63	0.1500	0.3878	0.7019	0.044*
H64	0.1505	0.4934	0.7820	0.046*
H65	0.1764	0.4197	0.8734	0.040*
H67a	0.2171	0.2614	0.9335	0.031*
H67b	0.1431	0.1882	0.9076	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0277 (4)	0.0217 (4)	0.0459 (5)	−0.0072 (3)	−0.0033 (3)	0.0056 (3)
Cl2	0.0369 (4)	0.0346 (5)	0.0225 (3)	−0.0038 (4)	0.0070 (3)	−0.0048 (3)
Cl3	0.0296 (4)	0.0260 (4)	0.0220 (3)	−0.0040 (3)	0.0064 (3)	0.0002 (3)
Cl4	0.0197 (3)	0.0275 (4)	0.0262 (4)	0.0008 (3)	0.0019 (3)	−0.0016 (3)
P1	0.0215 (4)	0.0237 (4)	0.0140 (3)	−0.0042 (3)	0.0028 (3)	−0.0049 (3)
O1	0.046 (2)	0.041 (2)	0.033 (1)	−0.025 (1)	0.013 (1)	−0.013 (1)
O2	0.034 (1)	0.040 (1)	0.017 (1)	0.008 (1)	−0.001 (1)	−0.004 (1)
O3	0.027 (1)	0.025 (1)	0.020 (1)	0.001 (1)	0.005 (1)	−0.005 (1)
O4	0.022 (1)	0.026 (1)	0.015 (1)	−0.002 (1)	0.003 (1)	−0.006 (1)
O5	0.034 (2)	0.184 (4)	0.058 (2)	−0.002 (2)	0.016 (1)	−0.019 (2)
O6	0.064 (2)	0.184 (5)	0.167 (4)	0.078 (3)	0.061 (3)	0.123 (4)
O7	0.248 (6)	0.044 (2)	0.066 (2)	−0.068 (3)	−0.049 (3)	0.009 (2)
O8	0.101 (3)	0.076 (2)	0.045 (2)	−0.037 (2)	0.017 (2)	−0.014 (2)
O9	0.050 (2)	0.058 (2)	0.123 (3)	−0.020 (2)	0.027 (2)	−0.020 (2)
O10	0.176 (4)	0.087 (3)	0.022 (1)	0.051 (3)	0.021 (2)	0.001 (2)
O11	0.085 (2)	0.058 (2)	0.084 (2)	−0.039 (2)	0.052 (2)	−0.032 (2)
O12	0.088 (3)	0.093 (3)	0.056 (2)	0.030 (2)	−0.026 (2)	0.007 (2)
O13	0.150 (4)	0.174 (5)	0.037 (2)	−0.007 (3)	0.040 (2)	0.035 (2)
O14	0.053 (2)	0.038 (2)	0.080 (2)	0.002 (1)	−0.005 (2)	−0.028 (1)
O15	0.026 (1)	0.036 (2)	0.123 (3)	0.007 (1)	0.017 (2)	0.007 (2)
O16	0.028 (1)	0.043 (2)	0.085 (2)	−0.011 (1)	−0.005 (1)	0.011 (1)
O17	0.040 (1)	0.028 (1)	0.044 (1)	−0.008 (1)	0.003 (1)	−0.007 (1)
O18	0.040 (1)	0.051 (2)	0.052 (2)	0.006 (1)	0.010 (1)	0.024 (1)
O19	0.021 (1)	0.091 (2)	0.073 (2)	0.001 (1)	−0.007 (1)	0.044 (2)
O20	0.095 (3)	0.059 (2)	0.077 (2)	−0.015 (2)	0.054 (2)	−0.038 (2)
O21	0.072 (2)	0.067 (2)	0.088 (3)	0.007 (2)	0.014 (2)	0.010 (2)
O22	0.056 (2)	0.139 (4)	0.074 (2)	0.020 (2)	0.006 (2)	−0.024 (2)
N1	0.016 (1)	0.018 (1)	0.018 (1)	0.000 (1)	0.001 (1)	−0.001 (1)
N2	0.019 (1)	0.023 (1)	0.018 (1)	0.000 (1)	0.005 (1)	−0.003 (1)
N11	0.020 (1)	0.025 (1)	0.019 (1)	0.003 (1)	−0.001 (1)	0.001 (1)
N21	0.020 (1)	0.020 (1)	0.025 (1)	0.000 (1)	0.005 (1)	0.002 (1)
N31	0.023 (1)	0.022 (1)	0.028 (1)	−0.003 (1)	0.003 (1)	−0.002 (1)
N41	0.021 (1)	0.028 (1)	0.019 (1)	0.002 (1)	0.006 (1)	0.004 (1)
N51	0.016 (1)	0.026 (1)	0.018 (1)	−0.002 (1)	0.002 (1)	−0.001 (1)
N61	0.024 (1)	0.025 (1)	0.025 (1)	0.002 (1)	0.005 (1)	0.002 (1)
C12	0.023 (2)	0.029 (2)	0.027 (2)	0.004 (1)	0.007 (1)	0.004 (1)
C13	0.021 (2)	0.026 (2)	0.036 (2)	−0.001 (1)	0.001 (1)	0.007 (1)
C14	0.027 (2)	0.022 (2)	0.031 (2)	−0.004 (1)	−0.007 (1)	−0.001 (1)
C15	0.030 (2)	0.020 (1)	0.023 (1)	0.000 (1)	−0.001 (1)	−0.002 (1)
C16	0.022 (1)	0.016 (1)	0.018 (1)	0.001 (1)	0.001 (1)	0.004 (1)
C17	0.022 (1)	0.022 (1)	0.017 (1)	0.001 (1)	0.002 (1)	0.003 (1)
C22	0.027 (2)	0.031 (2)	0.024 (1)	0.001 (1)	0.005 (1)	0.004 (1)
C23	0.030 (2)	0.031 (2)	0.033 (2)	0.005 (1)	0.007 (1)	0.013 (1)
C24	0.027 (2)	0.022 (2)	0.043 (2)	0.003 (1)	0.012 (1)	0.006 (1)
C25	0.022 (1)	0.022 (2)	0.033 (2)	0.000 (1)	0.008 (1)	−0.002 (1)
C26	0.015 (1)	0.022 (1)	0.025 (1)	−0.001 (1)	0.004 (1)	0.000 (1)
C27	0.023 (1)	0.019 (1)	0.024 (1)	−0.001 (1)	−0.001 (1)	−0.002 (1)
C32	0.038 (2)	0.028 (2)	0.047 (2)	−0.008 (2)	0.000 (2)	−0.010 (2)
C33	0.040 (2)	0.025 (2)	0.079 (3)	−0.011 (2)	0.002 (2)	−0.001 (2)
C34	0.034 (2)	0.038 (2)	0.076 (3)	−0.008 (2)	0.016 (2)	0.017 (2)
C35	0.032 (2)	0.037 (2)	0.044 (2)	−0.002 (2)	0.014 (2)	0.009 (2)
C36	0.016 (1)	0.027 (2)	0.027 (1)	0.001 (1)	0.001 (1)	0.004 (1)
C37	0.019 (1)	0.024 (2)	0.023 (1)	0.002 (1)	0.006 (1)	−0.001 (1)
C42	0.026 (2)	0.029 (2)	0.025 (1)	−0.001 (1)	0.004 (1)	0.003 (1)
C43	0.028 (2)	0.023 (2)	0.036 (2)	−0.001 (1)	0.010 (1)	0.005 (1)
C44	0.032 (2)	0.022 (2)	0.031 (2)	0.007 (1)	0.018 (1)	0.009 (1)
C45	0.032 (2)	0.025 (2)	0.021 (1)	0.008 (1)	0.010 (1)	0.004 (1)
C46	0.023 (1)	0.023 (2)	0.019 (1)	0.007 (1)	0.004 (1)	0.004 (1)
C47	0.026 (2)	0.034 (2)	0.016 (1)	0.003 (1)	0.006 (1)	0.001 (1)
C52	0.024 (1)	0.029 (2)	0.022 (1)	−0.001 (1)	0.008 (1)	−0.001 (1)
C53	0.022 (2)	0.032 (2)	0.033 (2)	0.004 (1)	0.009 (1)	0.004 (1)
C54	0.018 (1)	0.050 (2)	0.028 (2)	−0.001 (1)	0.002 (1)	0.007 (2)
C55	0.023 (2)	0.039 (2)	0.019 (1)	−0.006 (1)	0.002 (1)	0.000 (1)
C56	0.020 (1)	0.029 (2)	0.017 (1)	−0.004 (1)	0.004 (1)	−0.001 (1)
C57	0.024 (1)	0.030 (2)	0.023 (1)	−0.002 (1)	0.004 (1)	−0.007 (1)
C62	0.026 (2)	0.038 (2)	0.028 (2)	0.001 (1)	0.006 (1)	0.005 (1)
C63	0.030 (2)	0.041 (2)	0.040 (2)	0.004 (2)	0.009 (1)	0.014 (2)
C64	0.038 (2)	0.028 (2)	0.053 (2)	0.008 (2)	0.019 (2)	0.010 (2)
C65	0.035 (2)	0.026 (2)	0.042 (2)	0.003 (1)	0.014 (2)	0.000 (1)
C66	0.021 (1)	0.027 (2)	0.031 (2)	0.002 (1)	0.009 (1)	0.000 (1)
C67	0.026 (2)	0.027 (2)	0.024 (1)	0.003 (1)	0.009 (1)	−0.006 (1)

Geometric parameters (Å, º) top

Cl1—O5	1.390 (3)	C52—C53	1.376 (4)
Cl1—O6	1.363 (3)	C53—C54	1.382 (5)
Cl1—O7	1.407 (3)	C54—C55	1.376 (5)
Cl1—O8	1.418 (3)	C55—C56	1.379 (4)
Cl2—O9	1.425 (3)	C56—C57	1.498 (4)
Cl2—O10	1.392 (3)	C62—C63	1.370 (5)
Cl2—O11	1.426 (3)	C63—C64	1.379 (5)
Cl2—O12	1.422 (3)	C64—C65	1.388 (5)
Cl3—O13	1.391 (3)	C65—C66	1.372 (4)
Cl3—O14	1.411 (3)	C66—C67	1.505 (4)
Cl3—O15	1.436 (3)	O1—HO1	0.69 (4)
Cl3—O16	1.432 (2)	O21—HO21b	0.962
Cl4—O17	1.429 (2)	O21—HO21a	0.964
Cl4—O18	1.432 (2)	O22—HO22b	0.959
Cl4—O19	1.432 (2)	O22—HO22a	0.959
Cl4—O20	1.420 (3)	N11—HN11	0.950
P1—O1	1.586 (3)	N21—HN21	0.950
P1—O2	1.524 (2)	N31—HN31	0.950
P1—O3	1.518 (2)	N41—HN41	0.950
P1—O4	1.528 (2)	N51—HN51	0.950
N1—C17	1.481 (3)	N61—HN61	0.950
N1—C27	1.464 (4)	C12—H12	0.950
N1—C37	1.478 (4)	C13—H13	0.950
N2—C47	1.473 (4)	C14—H14	0.950
N2—C57	1.466 (4)	C15—H15	0.950
N2—C67	1.464 (4)	C17—H17a	0.950
N11—C12	1.342 (4)	C17—H17b	0.950
N11—C16	1.341 (4)	C22—H22	0.950
N21—C22	1.344 (4)	C23—H23	0.950
N21—C26	1.343 (4)	C24—H24	0.950
N31—C32	1.334 (4)	C25—H25	0.950
N31—C36	1.342 (4)	C27—H27a	0.950
N41—C42	1.342 (4)	C27—H27b	0.950
N41—C46	1.343 (4)	C32—H32	0.950
N51—C52	1.341 (4)	C33—H33	0.950
N51—C56	1.346 (4)	C34—H34	0.950
N61—C62	1.344 (4)	C35—H35	0.950
N61—C66	1.349 (4)	C37—H37a	0.950
C12—C13	1.380 (4)	C37—H37b	0.950
C13—C14	1.383 (4)	C42—H42	0.950
C14—C15	1.378 (4)	C43—H43	0.950
C15—C16	1.383 (4)	C44—H44	0.950
C16—C17	1.498 (4)	C45—H45	0.950
C22—C23	1.376 (4)	C47—H47a	0.950
C23—C24	1.387 (5)	C47—H47b	0.950
C24—C25	1.381 (4)	C52—H52	0.950
C25—C26	1.382 (4)	C53—H53	0.950
C26—C27	1.511 (4)	C54—H54	0.950
C32—C33	1.360 (5)	C55—H55	0.950
C33—C34	1.376 (6)	C57—H57a	0.950
C34—C35	1.383 (5)	C57—H57b	0.950
C35—C36	1.373 (4)	C62—H62	0.950
C36—C37	1.492 (4)	C63—H63	0.950
C42—C43	1.379 (4)	C64—H64	0.950
C43—C44	1.385 (4)	C65—H65	0.950
C44—C45	1.380 (4)	C67—H67b	0.950
C45—C46	1.386 (4)	C67—H67a	0.950
C46—C47	1.498 (4)

N11···N21	4.690 (3)	N41···N51	4.134 (3)
N21···N31	4.038 (3)	N51···N61	4.005 (3)
N11···N31	4.565 (3)	N41···N61	4.012 (4)

O5—Cl1—O6	108.0 (2)	HO21a—O21—HO21b	102.2
O5—Cl1—O7	113.7 (3)	HO22a—O22—HO22b	112.7
O5—Cl1—O8	109.1 (2)	C16—N11—HN11	119.3
O6—Cl1—O7	105.7 (3)	C12—N11—HN11	119.3
O6—Cl1—O8	115.2 (3)	C26—N21—HN21	118.6
O7—Cl1—O8	105.3 (2)	C22—N21—HN21	118.6
O9—Cl2—O10	109.7 (2)	C32—N31—HN31	118.6
O9—Cl2—O11	107.1 (2)	C36—N31—HN31	118.6
O9—Cl2—O12	107.5 (2)	C42—N41—HN41	118.6
O10—Cl2—O11	111.6 (2)	C46—N41—HN41	118.6
O10—Cl2—O12	109.4 (2)	C52—N51—HN51	118.5
O11—Cl2—O12	111.3 (2)	C56—N51—HN51	118.5
O13—Cl3—O14	110.5 (3)	C62—N61—HN61	118.4
O13—Cl3—O15	111.5 (2)	C66—N61—HN61	118.4
O13—Cl3—O16	108.5 (2)	N11—C12—H12	119.4
O14—Cl3—O15	108.6 (2)	C13—C12—H12	119.4
O14—Cl3—O16	109.5 (2)	C12—C13—H13	120.8
O15—Cl3—O16	108.2 (2)	C14—C13—H13	120.8
O17—Cl4—O18	110.7 (2)	C15—C14—H14	120.3
O17—Cl4—O19	109.0 (2)	C13—C14—H14	120.3
O17—Cl4—O20	108.8 (2)	C14—C15—H15	119.9
O18—Cl4—O19	108.3 (2)	C16—C15—H15	119.9
O18—Cl4—O20	109.2 (2)	H17a—C17—H17b	109.5
O19—Cl4—O20	110.8 (2)	N1—C17—H17a	108.3
O1—P1—O2	109.4 (1)	C16—C17—H17a	108.3
O1—P1—O3	108.7 (1)	N1—C17—H17b	108.3
O1—P1—O4	103.0 (1)	C16—C17—H17b	108.3
O2—P1—O3	112.4 (1)	N21—C22—H22	119.9
O2—P1—O4	111.1 (1)	C23—C22—H22	119.9
O3—P1—O4	111.7 (1)	C22—C23—H23	120.7
C17—N1—C27	111.9 (2)	C24—C23—H23	120.7
C17—N1—C37	108.4 (2)	C25—C24—H24	120.0
C27—N1—C37	109.2 (2)	C23—C24—H24	120.0
C47—N2—C57	110.6 (2)	C24—C25—H25	120.0
C47—N2—C67	112.2 (2)	C26—C25—H25	120.0
C57—N2—C67	109.8 (2)	H27a—C27—H27b	109.5
C12—N11—C16	121.4 (2)	N1—C27—H27a	108.7
C22—N21—C26	122.8 (3)	C26—C27—H27a	108.7
C32—N31—C36	122.8 (3)	N1—C27—H27b	108.7
C42—N41—C46	122.9 (2)	C26—C27—H27b	108.7
C52—N51—C56	123.0 (2)	N31—C32—H32	119.8
C62—N61—C66	123.2 (3)	C33—C32—H32	119.8
N11—C12—C13	121.2 (3)	C32—C33—H33	120.5
C12—C13—C14	118.4 (3)	C34—C33—H33	120.5
C13—C14—C15	119.5 (3)	C33—C34—H34	120.2
C14—C15—C16	120.2 (3)	C35—C34—H34	120.2
N11—C16—C15	119.3 (3)	C36—C35—H35	120.1
N11—C16—C17	119.0 (2)	C34—C35—H35	120.1
C15—C16—C17	121.6 (3)	H37a—C37—H37b	109.5
N1—C17—C16	114.0 (2)	N1—C37—H37a	108.9
N21—C22—C23	120.2 (3)	C36—C37—H37a	108.8
C22—C23—C24	118.5 (3)	N1—C37—H37b	108.9
C23—C24—C25	119.9 (3)	C36—C37—H37b	108.8
C24—C25—C26	120.1 (3)	N41—C42—H42	119.8
N21—C26—C25	118.5 (3)	C43—C42—H42	119.8
N21—C26—C27	118.8 (3)	C42—C43—H43	120.8
C25—C26—C27	122.7 (3)	C44—C43—H43	120.8
N1—C27—C26	112.4 (2)	C45—C44—H44	120.0
N31—C32—C33	120.3 (3)	C43—C44—H44	120.0
C32—C33—C34	118.9 (3)	C44—C45—H45	119.9
C33—C34—C35	119.7 (3)	C46—C45—H45	119.9
C34—C35—C36	119.8 (3)	H47a—C47—H47b	109.5
N31—C36—C35	118.4 (3)	N2—C47—H47a	108.5
N31—C36—C37	117.8 (3)	C46—C47—H47a	108.5
C35—C36—C37	123.8 (3)	N2—C47—H47b	108.5
N1—C37—C36	112.0 (2)	C46—C47—H47b	108.5
N41—C42—C43	120.4 (3)	N51—C52—H52	120.1
C42—C43—C44	118.4 (3)	C53—C52—H52	120.1
C43—C44—C45	120.0 (3)	C52—C53—H53	120.8
C44—C45—C46	120.1 (3)	C54—C53—H53	120.8
N41—C46—C45	118.3 (3)	C55—C54—H54	119.7
N41—C46—C47	118.6 (2)	C53—C54—H54	119.7
C45—C46—C47	123.0 (3)	C54—C55—H55	120.2
N2—C47—C46	113.4 (2)	C56—C55—H55	120.2
N51—C52—C53	119.9 (3)	H57a—C57—H57b	109.5
C52—C53—C54	118.5 (3)	N2—C57—H57a	108.6
C53—C54—C55	120.5 (3)	C56—C57—H57a	108.6
C54—C55—C56	119.6 (3)	N2—C57—H57b	108.6
N51—C56—C55	118.6 (3)	C56—C57—H57b	108.6
N51—C56—C57	118.1 (2)	N61—C62—H62	120.0
C55—C56—C57	123.2 (3)	C63—C62—H62	120.1
N2—C57—C56	112.8 (2)	C62—C63—H63	120.7
N61—C62—C63	119.9 (3)	C64—C63—H63	120.7
C62—C63—C64	118.7 (3)	C63—C64—H64	120.0
C63—C64—C65	120.1 (3)	C65—C64—H64	120.0
C64—C65—C66	120.0 (3)	C66—C65—H65	120.0
N61—C66—C65	118.1 (3)	C64—C65—H65	120.0
N61—C66—C67	117.4 (3)	H67a—C67—H67b	109.5
C65—C66—C67	124.4 (3)	N2—C67—H67b	108.9
N2—C67—C66	111.7 (2)	C66—C67—H67b	108.9
P1—O1—HO1	118 (4)	N2—C67—H67a	108.9
P1—O2—HN11	123.3	C66—C67—H67a	108.9

N1—C17—C16—N11	66.4 (3)	C46—C47—N2—C57	−167.1 (2)
N1—C17—C16—C15	−116.5 (3)	C46—C47—N2—C67	70.0 (3)
N1—C27—C26—N21	26.1 (4)	C56—C57—N2—C47	71.1 (3)
N1—C27—C26—C25	−156.5 (3)	C56—C57—N2—C67	−164.6 (2)
N1—C37—C36—N31	50.2 (3)	C66—C67—N2—C47	−160.5 (2)
N1—C37—C36—C35	−132.2 (3)	C66—C67—N2—C57	76.1 (3)
N2—C47—C46—N41	43.2 (4)	N2—C47—C46—N41	43.2 (4)
N2—C47—C46—C45	−140.3 (3)	N2—C47—C46—C45	−140.3 (3)
N2—C57—C56—N51	39.3 (4)	N2—C57—C56—N51	39.3 (4)
N2—C57—C56—C55	−143.7 (3)	N2—C57—C56—C55	−143.7 (3)
N2—C67—C66—N61	37.1 (4)	N2—C67—C66—N61	37.1 (4)
N2—C67—C66—C65	−145.4 (3)	N2—C67—C66—C65	−145.4 (3)
C16—C17—N1—C27	59.1 (3)	N1—C17—C16—N11	66.4 (3)
C16—C17—N1—C37	179.5 (3)	N1—C17—C16—C15	−116.5 (3)
C26—C27—N1—C17	−167.4 (2)	N1—C27—C26—N21	26.1 (4)
C26—C27—N1—C37	72.6 (3)	N1—C27—C26—C25	−156.5 (3)
C36—C37—N1—C17	65.9 (3)	N1—C37—C36—N31	50.2 (3)
C36—C37—N1—C27	−172.0 (2)	N1—C37—C36—C35	−132.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—HO1···O7	0.69 (4)	2.00 (4)	2.675 (4)	165 (5)
O21—HO21a···O22	0.96	1.82	2.756 (5)	163
O21—HO21b···O9	0.96	2.07	2.895 (5)	143
O22—HO22a···O2ⁱ	0.96	1.84	2.796 (4)	174
O22—HO22b···O5ⁱⁱ	0.96	1.93	2.861 (5)	163
N11—HN11···O2	0.95	1.68	2.578 (3)	156
N21—HN21···O3	0.95	1.76	2.648 (3)	155
N31—HN31···O3	0.95	1.72	2.658 (3)	169
N41—HN41···O4	0.95	1.78	2.724 (3)	172
N51—HN51···O4	0.95	1.78	2.719 (3)	167
N61—HN61···O4	0.95	1.76	2.688 (3)	166

Symmetry codes: (i) −x, −y, −z+1; (ii) x, −y−1/2, z−1/2.

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Hydrogen bonding in 2,2',2''-(nitrilo­trimethyl­ene)tripyridinium hydrogenphosphate tetra­kis(perchlorate) dihydrate and related compounds