organic compounds
In the title salt, 2C18H21N43+·HPO42-.4 ClO4-·2H2O. the protons of each of the pyridyl N atoms are hydrogen bonded to one HPO42- 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.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605080X/jh2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680605080X/jh2046Isup2.hkl |
CCDC reference: 630036
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 |
Mr = 1116.64 | Dx = 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 | Rint = 0.031 |
ω rotation scans with narrow frames | θmax = 29.8°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −22→22 |
Tmin = 0.692, Tmax = 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/{[σcs(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 | Δρmax = 0.81 (8) e Å−3 |
644 parameters | Δρmin = −1.12 (8) e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
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. |