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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680605080X/jh2046sup1.cif
Contains datablocks fos, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680605080X/jh2046Isup2.hkl
Contains datablock I

CCDC reference: 630036

Key indicators

  • Single-crystal X-ray study
  • T = 120 K
  • Mean [sigma](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+·HO4P2·4ClO4·2H2OF(000) = 2312.0
Mr = 1116.64Dx = 1.533 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8192 reflections
a = 16.1366 (7) Åθ = 2.0–29.8°
b = 12.8104 (6) ŵ = 0.37 mm1
c = 23.832 (1) ÅT = 120 K
β = 100.988 (1)°Plate, colourless
V = 4836.1 (4) Å30.44 × 0.44 × 0.14 mm
Z = 4
Data collection top
Siemens SMART CCD
diffractometer
13850 independent reflections
Radiation source: x-ray tube9018 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.031
ω rotation scans with narrow framesθmax = 29.8°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2222
Tmin = 0.692, Tmax = 0.953k = 1518
45366 measured reflectionsl = 3332
Refinement top
Refinement on F0 restraints
Least-squares matrix: full0 constraints
R[F2 > 2σ(F2)] = 0.053H 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 reflectionsΔρmax = 0.81 (8) e Å3
644 parametersΔρmin = 1.12 (8) e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.04627 (5)0.35651 (6)0.65619 (4)0.0331 (4)
Cl20.32818 (5)0.25605 (7)0.42885 (3)0.0312 (4)
Cl30.23618 (5)0.25594 (6)0.57717 (3)0.0257 (4)
Cl40.55280 (4)0.22233 (6)0.70648 (3)0.0248 (4)
P10.20718 (5)0.05652 (6)0.74201 (3)0.0198 (4)
O10.1496 (2)0.1491 (2)0.7567 (1)0.039 (2)
O20.1589 (1)0.0060 (2)0.6919 (1)0.031 (1)
O30.2886 (1)0.1021 (2)0.7295 (1)0.024 (1)
O40.2227 (1)0.0084 (2)0.7968 (1)0.021 (1)
O50.0228 (2)0.3735 (4)0.6821 (1)0.091 (3)
O60.1103 (2)0.4195 (4)0.6822 (2)0.134 (4)
O70.0782 (3)0.2541 (3)0.6629 (2)0.130 (4)
O80.0213 (2)0.3710 (3)0.5964 (1)0.074 (2)
O90.2426 (2)0.2668 (3)0.4353 (2)0.075 (2)
O100.3332 (3)0.2651 (3)0.3714 (1)0.094 (3)
O110.3565 (2)0.1563 (2)0.4513 (1)0.071 (2)
O120.3751 (2)0.3380 (3)0.4603 (1)0.084 (3)
O130.2384 (3)0.2303 (4)0.6342 (1)0.118 (4)
O140.2325 (2)0.1649 (2)0.5435 (1)0.059 (2)
O150.1645 (2)0.3200 (2)0.5549 (1)0.061 (2)
O160.3110 (2)0.3134 (2)0.5734 (1)0.054 (2)
O170.4995 (1)0.3109 (2)0.6908 (1)0.038 (1)
O180.5562 (2)0.1587 (2)0.6576 (1)0.047 (2)
O190.6366 (1)0.2576 (3)0.7296 (1)0.064 (2)
O200.5198 (2)0.1626 (2)0.7474 (1)0.072 (2)
O210.1332 (2)0.1013 (3)0.3816 (2)0.076 (2)
O220.0148 (2)0.1242 (3)0.3030 (2)0.091 (3)
N10.2676 (1)0.1724 (2)0.5980 (1)0.018 (1)
N20.2558 (1)0.1265 (2)0.9064 (1)0.020 (1)
N110.0938 (1)0.0688 (2)0.5929 (1)0.022 (1)
N210.2944 (1)0.2979 (2)0.6949 (1)0.022 (1)
N310.3749 (2)0.0120 (2)0.6582 (1)0.025 (1)
N410.1404 (1)0.0470 (2)0.8821 (1)0.022 (1)
N510.3819 (1)0.0229 (2)0.8593 (1)0.020 (1)
N610.1880 (2)0.2132 (2)0.8000 (1)0.025 (1)
C120.0103 (2)0.0650 (2)0.5913 (1)0.026 (2)
C130.0463 (2)0.1020 (3)0.5448 (1)0.028 (2)
C140.0150 (2)0.1443 (2)0.4996 (1)0.028 (2)
C150.0710 (2)0.1477 (2)0.5022 (1)0.025 (2)
C160.1255 (2)0.1090 (2)0.5495 (1)0.019 (1)
C170.2190 (2)0.1063 (2)0.5523 (1)0.021 (1)
C220.3231 (2)0.3490 (3)0.7440 (1)0.027 (2)
C230.3355 (2)0.4552 (3)0.7437 (1)0.031 (2)
C240.3168 (2)0.5077 (2)0.6919 (1)0.030 (2)
C250.2879 (2)0.4529 (2)0.6421 (1)0.025 (2)
C260.2768 (2)0.3461 (2)0.6439 (1)0.021 (1)
C270.2423 (2)0.2822 (2)0.5914 (1)0.023 (1)
C320.4055 (2)0.0810 (3)0.6771 (2)0.039 (2)
C330.4556 (2)0.1358 (3)0.6477 (2)0.049 (2)
C340.4716 (2)0.0954 (3)0.5973 (2)0.048 (3)
C350.4388 (2)0.0008 (3)0.5784 (2)0.037 (2)
C360.3909 (2)0.0557 (2)0.6102 (1)0.024 (2)
C370.3581 (2)0.1632 (2)0.5956 (1)0.022 (1)
C420.0720 (2)0.1073 (2)0.8657 (1)0.027 (2)
C430.0223 (2)0.1349 (2)0.9044 (1)0.028 (2)
C440.0444 (2)0.0985 (2)0.9599 (1)0.027 (2)
C450.1149 (2)0.0363 (2)0.9754 (1)0.025 (2)
C460.1640 (2)0.0108 (2)0.9356 (1)0.022 (1)
C470.2445 (2)0.0500 (3)0.9504 (1)0.025 (2)
C520.4343 (2)0.0471 (2)0.8428 (1)0.024 (2)
C530.5150 (2)0.0582 (3)0.8738 (1)0.028 (2)
C540.5399 (2)0.0042 (3)0.9213 (1)0.032 (2)
C550.4853 (2)0.0765 (3)0.9367 (1)0.027 (2)
C560.4048 (2)0.0857 (2)0.9048 (1)0.022 (1)
C570.3427 (2)0.1657 (2)0.9167 (1)0.026 (2)
C620.1763 (2)0.2540 (3)0.7471 (1)0.030 (2)
C630.1606 (2)0.3586 (3)0.7392 (1)0.037 (2)
C640.1605 (2)0.4206 (3)0.7865 (2)0.038 (2)
C650.1750 (2)0.3766 (3)0.8408 (1)0.034 (2)
C660.1873 (2)0.2710 (2)0.8472 (1)0.026 (2)
C670.1967 (2)0.2141 (2)0.9033 (1)0.026 (2)
HO10.124 (3)0.174 (3)0.734 (2)0.05 (1)*
HO21a0.08730.11940.35100.150*
HO21b0.17080.15980.38200.150*
HO22a0.06560.08740.30590.150*
HO22b0.00640.12960.26430.150*
HN110.13130.04240.62540.026*
HN210.28620.22460.69630.026*
HN310.34040.04880.67960.029*
HN410.17350.02910.85450.027*
HN510.32610.02840.83770.024*
HN610.19730.14020.80440.030*
H120.01010.03640.62280.032*
H130.10540.09850.54380.034*
H140.05250.17090.46710.034*
H150.09290.17670.47130.030*
H17a0.23020.12960.51660.025*
H17b0.23760.03620.55870.025*
H220.33490.31160.77910.033*
H230.35650.49180.77810.037*
H240.32370.58130.69070.036*
H250.27580.48860.60650.030*
H27a0.26280.31050.55980.027*
H27b0.18250.28600.58430.027*
H320.39230.10910.71120.046*
H330.47910.20090.66170.059*
H340.50510.13340.57560.058*
H350.44930.02890.54360.044*
H37a0.36570.17990.55810.026*
H37b0.38910.21100.62210.026*
H420.05790.13110.82730.032*
H430.02600.17790.89320.034*
H440.01110.11630.98740.032*
H450.12970.01081.01350.031*
H47a0.24470.08620.98520.030*
H47b0.29040.00230.95530.030*
H520.41570.08900.80990.029*
H530.55270.10770.86270.034*
H540.59520.00270.94340.038*
H550.50290.11980.96920.033*
H57a0.35780.18650.95560.031*
H57b0.34530.22430.89260.031*
H620.17890.21030.71530.036*
H630.15000.38780.70190.044*
H640.15050.49340.78200.046*
H650.17640.41970.87340.040*
H67a0.21710.26140.93350.031*
H67b0.14310.18820.90760.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0277 (4)0.0217 (4)0.0459 (5)0.0072 (3)0.0033 (3)0.0056 (3)
Cl20.0369 (4)0.0346 (5)0.0225 (3)0.0038 (4)0.0070 (3)0.0048 (3)
Cl30.0296 (4)0.0260 (4)0.0220 (3)0.0040 (3)0.0064 (3)0.0002 (3)
Cl40.0197 (3)0.0275 (4)0.0262 (4)0.0008 (3)0.0019 (3)0.0016 (3)
P10.0215 (4)0.0237 (4)0.0140 (3)0.0042 (3)0.0028 (3)0.0049 (3)
O10.046 (2)0.041 (2)0.033 (1)0.025 (1)0.013 (1)0.013 (1)
O20.034 (1)0.040 (1)0.017 (1)0.008 (1)0.001 (1)0.004 (1)
O30.027 (1)0.025 (1)0.020 (1)0.001 (1)0.005 (1)0.005 (1)
O40.022 (1)0.026 (1)0.015 (1)0.002 (1)0.003 (1)0.006 (1)
O50.034 (2)0.184 (4)0.058 (2)0.002 (2)0.016 (1)0.019 (2)
O60.064 (2)0.184 (5)0.167 (4)0.078 (3)0.061 (3)0.123 (4)
O70.248 (6)0.044 (2)0.066 (2)0.068 (3)0.049 (3)0.009 (2)
O80.101 (3)0.076 (2)0.045 (2)0.037 (2)0.017 (2)0.014 (2)
O90.050 (2)0.058 (2)0.123 (3)0.020 (2)0.027 (2)0.020 (2)
O100.176 (4)0.087 (3)0.022 (1)0.051 (3)0.021 (2)0.001 (2)
O110.085 (2)0.058 (2)0.084 (2)0.039 (2)0.052 (2)0.032 (2)
O120.088 (3)0.093 (3)0.056 (2)0.030 (2)0.026 (2)0.007 (2)
O130.150 (4)0.174 (5)0.037 (2)0.007 (3)0.040 (2)0.035 (2)
O140.053 (2)0.038 (2)0.080 (2)0.002 (1)0.005 (2)0.028 (1)
O150.026 (1)0.036 (2)0.123 (3)0.007 (1)0.017 (2)0.007 (2)
O160.028 (1)0.043 (2)0.085 (2)0.011 (1)0.005 (1)0.011 (1)
O170.040 (1)0.028 (1)0.044 (1)0.008 (1)0.003 (1)0.007 (1)
O180.040 (1)0.051 (2)0.052 (2)0.006 (1)0.010 (1)0.024 (1)
O190.021 (1)0.091 (2)0.073 (2)0.001 (1)0.007 (1)0.044 (2)
O200.095 (3)0.059 (2)0.077 (2)0.015 (2)0.054 (2)0.038 (2)
O210.072 (2)0.067 (2)0.088 (3)0.007 (2)0.014 (2)0.010 (2)
O220.056 (2)0.139 (4)0.074 (2)0.020 (2)0.006 (2)0.024 (2)
N10.016 (1)0.018 (1)0.018 (1)0.000 (1)0.001 (1)0.001 (1)
N20.019 (1)0.023 (1)0.018 (1)0.000 (1)0.005 (1)0.003 (1)
N110.020 (1)0.025 (1)0.019 (1)0.003 (1)0.001 (1)0.001 (1)
N210.020 (1)0.020 (1)0.025 (1)0.000 (1)0.005 (1)0.002 (1)
N310.023 (1)0.022 (1)0.028 (1)0.003 (1)0.003 (1)0.002 (1)
N410.021 (1)0.028 (1)0.019 (1)0.002 (1)0.006 (1)0.004 (1)
N510.016 (1)0.026 (1)0.018 (1)0.002 (1)0.002 (1)0.001 (1)
N610.024 (1)0.025 (1)0.025 (1)0.002 (1)0.005 (1)0.002 (1)
C120.023 (2)0.029 (2)0.027 (2)0.004 (1)0.007 (1)0.004 (1)
C130.021 (2)0.026 (2)0.036 (2)0.001 (1)0.001 (1)0.007 (1)
C140.027 (2)0.022 (2)0.031 (2)0.004 (1)0.007 (1)0.001 (1)
C150.030 (2)0.020 (1)0.023 (1)0.000 (1)0.001 (1)0.002 (1)
C160.022 (1)0.016 (1)0.018 (1)0.001 (1)0.001 (1)0.004 (1)
C170.022 (1)0.022 (1)0.017 (1)0.001 (1)0.002 (1)0.003 (1)
C220.027 (2)0.031 (2)0.024 (1)0.001 (1)0.005 (1)0.004 (1)
C230.030 (2)0.031 (2)0.033 (2)0.005 (1)0.007 (1)0.013 (1)
C240.027 (2)0.022 (2)0.043 (2)0.003 (1)0.012 (1)0.006 (1)
C250.022 (1)0.022 (2)0.033 (2)0.000 (1)0.008 (1)0.002 (1)
C260.015 (1)0.022 (1)0.025 (1)0.001 (1)0.004 (1)0.000 (1)
C270.023 (1)0.019 (1)0.024 (1)0.001 (1)0.001 (1)0.002 (1)
C320.038 (2)0.028 (2)0.047 (2)0.008 (2)0.000 (2)0.010 (2)
C330.040 (2)0.025 (2)0.079 (3)0.011 (2)0.002 (2)0.001 (2)
C340.034 (2)0.038 (2)0.076 (3)0.008 (2)0.016 (2)0.017 (2)
C350.032 (2)0.037 (2)0.044 (2)0.002 (2)0.014 (2)0.009 (2)
C360.016 (1)0.027 (2)0.027 (1)0.001 (1)0.001 (1)0.004 (1)
C370.019 (1)0.024 (2)0.023 (1)0.002 (1)0.006 (1)0.001 (1)
C420.026 (2)0.029 (2)0.025 (1)0.001 (1)0.004 (1)0.003 (1)
C430.028 (2)0.023 (2)0.036 (2)0.001 (1)0.010 (1)0.005 (1)
C440.032 (2)0.022 (2)0.031 (2)0.007 (1)0.018 (1)0.009 (1)
C450.032 (2)0.025 (2)0.021 (1)0.008 (1)0.010 (1)0.004 (1)
C460.023 (1)0.023 (2)0.019 (1)0.007 (1)0.004 (1)0.004 (1)
C470.026 (2)0.034 (2)0.016 (1)0.003 (1)0.006 (1)0.001 (1)
C520.024 (1)0.029 (2)0.022 (1)0.001 (1)0.008 (1)0.001 (1)
C530.022 (2)0.032 (2)0.033 (2)0.004 (1)0.009 (1)0.004 (1)
C540.018 (1)0.050 (2)0.028 (2)0.001 (1)0.002 (1)0.007 (2)
C550.023 (2)0.039 (2)0.019 (1)0.006 (1)0.002 (1)0.000 (1)
C560.020 (1)0.029 (2)0.017 (1)0.004 (1)0.004 (1)0.001 (1)
C570.024 (1)0.030 (2)0.023 (1)0.002 (1)0.004 (1)0.007 (1)
C620.026 (2)0.038 (2)0.028 (2)0.001 (1)0.006 (1)0.005 (1)
C630.030 (2)0.041 (2)0.040 (2)0.004 (2)0.009 (1)0.014 (2)
C640.038 (2)0.028 (2)0.053 (2)0.008 (2)0.019 (2)0.010 (2)
C650.035 (2)0.026 (2)0.042 (2)0.003 (1)0.014 (2)0.000 (1)
C660.021 (1)0.027 (2)0.031 (2)0.002 (1)0.009 (1)0.000 (1)
C670.026 (2)0.027 (2)0.024 (1)0.003 (1)0.009 (1)0.006 (1)
Geometric parameters (Å, º) top
Cl1—O51.390 (3)C52—C531.376 (4)
Cl1—O61.363 (3)C53—C541.382 (5)
Cl1—O71.407 (3)C54—C551.376 (5)
Cl1—O81.418 (3)C55—C561.379 (4)
Cl2—O91.425 (3)C56—C571.498 (4)
Cl2—O101.392 (3)C62—C631.370 (5)
Cl2—O111.426 (3)C63—C641.379 (5)
Cl2—O121.422 (3)C64—C651.388 (5)
Cl3—O131.391 (3)C65—C661.372 (4)
Cl3—O141.411 (3)C66—C671.505 (4)
Cl3—O151.436 (3)O1—HO10.69 (4)
Cl3—O161.432 (2)O21—HO21b0.962
Cl4—O171.429 (2)O21—HO21a0.964
Cl4—O181.432 (2)O22—HO22b0.959
Cl4—O191.432 (2)O22—HO22a0.959
Cl4—O201.420 (3)N11—HN110.950
P1—O11.586 (3)N21—HN210.950
P1—O21.524 (2)N31—HN310.950
P1—O31.518 (2)N41—HN410.950
P1—O41.528 (2)N51—HN510.950
N1—C171.481 (3)N61—HN610.950
N1—C271.464 (4)C12—H120.950
N1—C371.478 (4)C13—H130.950
N2—C471.473 (4)C14—H140.950
N2—C571.466 (4)C15—H150.950
N2—C671.464 (4)C17—H17a0.950
N11—C121.342 (4)C17—H17b0.950
N11—C161.341 (4)C22—H220.950
N21—C221.344 (4)C23—H230.950
N21—C261.343 (4)C24—H240.950
N31—C321.334 (4)C25—H250.950
N31—C361.342 (4)C27—H27a0.950
N41—C421.342 (4)C27—H27b0.950
N41—C461.343 (4)C32—H320.950
N51—C521.341 (4)C33—H330.950
N51—C561.346 (4)C34—H340.950
N61—C621.344 (4)C35—H350.950
N61—C661.349 (4)C37—H37a0.950
C12—C131.380 (4)C37—H37b0.950
C13—C141.383 (4)C42—H420.950
C14—C151.378 (4)C43—H430.950
C15—C161.383 (4)C44—H440.950
C16—C171.498 (4)C45—H450.950
C22—C231.376 (4)C47—H47a0.950
C23—C241.387 (5)C47—H47b0.950
C24—C251.381 (4)C52—H520.950
C25—C261.382 (4)C53—H530.950
C26—C271.511 (4)C54—H540.950
C32—C331.360 (5)C55—H550.950
C33—C341.376 (6)C57—H57a0.950
C34—C351.383 (5)C57—H57b0.950
C35—C361.373 (4)C62—H620.950
C36—C371.492 (4)C63—H630.950
C42—C431.379 (4)C64—H640.950
C43—C441.385 (4)C65—H650.950
C44—C451.380 (4)C67—H67b0.950
C45—C461.386 (4)C67—H67a0.950
C46—C471.498 (4)
N11···N214.690 (3)N41···N514.134 (3)
N21···N314.038 (3)N51···N614.005 (3)
N11···N314.565 (3)N41···N614.012 (4)
O5—Cl1—O6108.0 (2)HO21a—O21—HO21b102.2
O5—Cl1—O7113.7 (3)HO22a—O22—HO22b112.7
O5—Cl1—O8109.1 (2)C16—N11—HN11119.3
O6—Cl1—O7105.7 (3)C12—N11—HN11119.3
O6—Cl1—O8115.2 (3)C26—N21—HN21118.6
O7—Cl1—O8105.3 (2)C22—N21—HN21118.6
O9—Cl2—O10109.7 (2)C32—N31—HN31118.6
O9—Cl2—O11107.1 (2)C36—N31—HN31118.6
O9—Cl2—O12107.5 (2)C42—N41—HN41118.6
O10—Cl2—O11111.6 (2)C46—N41—HN41118.6
O10—Cl2—O12109.4 (2)C52—N51—HN51118.5
O11—Cl2—O12111.3 (2)C56—N51—HN51118.5
O13—Cl3—O14110.5 (3)C62—N61—HN61118.4
O13—Cl3—O15111.5 (2)C66—N61—HN61118.4
O13—Cl3—O16108.5 (2)N11—C12—H12119.4
O14—Cl3—O15108.6 (2)C13—C12—H12119.4
O14—Cl3—O16109.5 (2)C12—C13—H13120.8
O15—Cl3—O16108.2 (2)C14—C13—H13120.8
O17—Cl4—O18110.7 (2)C15—C14—H14120.3
O17—Cl4—O19109.0 (2)C13—C14—H14120.3
O17—Cl4—O20108.8 (2)C14—C15—H15119.9
O18—Cl4—O19108.3 (2)C16—C15—H15119.9
O18—Cl4—O20109.2 (2)H17a—C17—H17b109.5
O19—Cl4—O20110.8 (2)N1—C17—H17a108.3
O1—P1—O2109.4 (1)C16—C17—H17a108.3
O1—P1—O3108.7 (1)N1—C17—H17b108.3
O1—P1—O4103.0 (1)C16—C17—H17b108.3
O2—P1—O3112.4 (1)N21—C22—H22119.9
O2—P1—O4111.1 (1)C23—C22—H22119.9
O3—P1—O4111.7 (1)C22—C23—H23120.7
C17—N1—C27111.9 (2)C24—C23—H23120.7
C17—N1—C37108.4 (2)C25—C24—H24120.0
C27—N1—C37109.2 (2)C23—C24—H24120.0
C47—N2—C57110.6 (2)C24—C25—H25120.0
C47—N2—C67112.2 (2)C26—C25—H25120.0
C57—N2—C67109.8 (2)H27a—C27—H27b109.5
C12—N11—C16121.4 (2)N1—C27—H27a108.7
C22—N21—C26122.8 (3)C26—C27—H27a108.7
C32—N31—C36122.8 (3)N1—C27—H27b108.7
C42—N41—C46122.9 (2)C26—C27—H27b108.7
C52—N51—C56123.0 (2)N31—C32—H32119.8
C62—N61—C66123.2 (3)C33—C32—H32119.8
N11—C12—C13121.2 (3)C32—C33—H33120.5
C12—C13—C14118.4 (3)C34—C33—H33120.5
C13—C14—C15119.5 (3)C33—C34—H34120.2
C14—C15—C16120.2 (3)C35—C34—H34120.2
N11—C16—C15119.3 (3)C36—C35—H35120.1
N11—C16—C17119.0 (2)C34—C35—H35120.1
C15—C16—C17121.6 (3)H37a—C37—H37b109.5
N1—C17—C16114.0 (2)N1—C37—H37a108.9
N21—C22—C23120.2 (3)C36—C37—H37a108.8
C22—C23—C24118.5 (3)N1—C37—H37b108.9
C23—C24—C25119.9 (3)C36—C37—H37b108.8
C24—C25—C26120.1 (3)N41—C42—H42119.8
N21—C26—C25118.5 (3)C43—C42—H42119.8
N21—C26—C27118.8 (3)C42—C43—H43120.8
C25—C26—C27122.7 (3)C44—C43—H43120.8
N1—C27—C26112.4 (2)C45—C44—H44120.0
N31—C32—C33120.3 (3)C43—C44—H44120.0
C32—C33—C34118.9 (3)C44—C45—H45119.9
C33—C34—C35119.7 (3)C46—C45—H45119.9
C34—C35—C36119.8 (3)H47a—C47—H47b109.5
N31—C36—C35118.4 (3)N2—C47—H47a108.5
N31—C36—C37117.8 (3)C46—C47—H47a108.5
C35—C36—C37123.8 (3)N2—C47—H47b108.5
N1—C37—C36112.0 (2)C46—C47—H47b108.5
N41—C42—C43120.4 (3)N51—C52—H52120.1
C42—C43—C44118.4 (3)C53—C52—H52120.1
C43—C44—C45120.0 (3)C52—C53—H53120.8
C44—C45—C46120.1 (3)C54—C53—H53120.8
N41—C46—C45118.3 (3)C55—C54—H54119.7
N41—C46—C47118.6 (2)C53—C54—H54119.7
C45—C46—C47123.0 (3)C54—C55—H55120.2
N2—C47—C46113.4 (2)C56—C55—H55120.2
N51—C52—C53119.9 (3)H57a—C57—H57b109.5
C52—C53—C54118.5 (3)N2—C57—H57a108.6
C53—C54—C55120.5 (3)C56—C57—H57a108.6
C54—C55—C56119.6 (3)N2—C57—H57b108.6
N51—C56—C55118.6 (3)C56—C57—H57b108.6
N51—C56—C57118.1 (2)N61—C62—H62120.0
C55—C56—C57123.2 (3)C63—C62—H62120.1
N2—C57—C56112.8 (2)C62—C63—H63120.7
N61—C62—C63119.9 (3)C64—C63—H63120.7
C62—C63—C64118.7 (3)C63—C64—H64120.0
C63—C64—C65120.1 (3)C65—C64—H64120.0
C64—C65—C66120.0 (3)C66—C65—H65120.0
N61—C66—C65118.1 (3)C64—C65—H65120.0
N61—C66—C67117.4 (3)H67a—C67—H67b109.5
C65—C66—C67124.4 (3)N2—C67—H67b108.9
N2—C67—C66111.7 (2)C66—C67—H67b108.9
P1—O1—HO1118 (4)N2—C67—H67a108.9
P1—O2—HN11123.3C66—C67—H67a108.9
N1—C17—C16—N1166.4 (3)C46—C47—N2—C57167.1 (2)
N1—C17—C16—C15116.5 (3)C46—C47—N2—C6770.0 (3)
N1—C27—C26—N2126.1 (4)C56—C57—N2—C4771.1 (3)
N1—C27—C26—C25156.5 (3)C56—C57—N2—C67164.6 (2)
N1—C37—C36—N3150.2 (3)C66—C67—N2—C47160.5 (2)
N1—C37—C36—C35132.2 (3)C66—C67—N2—C5776.1 (3)
N2—C47—C46—N4143.2 (4)N2—C47—C46—N4143.2 (4)
N2—C47—C46—C45140.3 (3)N2—C47—C46—C45140.3 (3)
N2—C57—C56—N5139.3 (4)N2—C57—C56—N5139.3 (4)
N2—C57—C56—C55143.7 (3)N2—C57—C56—C55143.7 (3)
N2—C67—C66—N6137.1 (4)N2—C67—C66—N6137.1 (4)
N2—C67—C66—C65145.4 (3)N2—C67—C66—C65145.4 (3)
C16—C17—N1—C2759.1 (3)N1—C17—C16—N1166.4 (3)
C16—C17—N1—C37179.5 (3)N1—C17—C16—C15116.5 (3)
C26—C27—N1—C17167.4 (2)N1—C27—C26—N2126.1 (4)
C26—C27—N1—C3772.6 (3)N1—C27—C26—C25156.5 (3)
C36—C37—N1—C1765.9 (3)N1—C37—C36—N3150.2 (3)
C36—C37—N1—C27172.0 (2)N1—C37—C36—C35132.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HO1···O70.69 (4)2.00 (4)2.675 (4)165 (5)
O21—HO21a···O220.961.822.756 (5)163
O21—HO21b···O90.962.072.895 (5)143
O22—HO22a···O2i0.961.842.796 (4)174
O22—HO22b···O5ii0.961.932.861 (5)163
N11—HN11···O20.951.682.578 (3)156
N21—HN21···O30.951.762.648 (3)155
N31—HN31···O30.951.722.658 (3)169
N41—HN41···O40.951.782.724 (3)172
N51—HN51···O40.951.782.719 (3)167
N61—HN61···O40.951.762.688 (3)166
Symmetry codes: (i) x, y, z+1; (ii) x, y1/2, z1/2.
 

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