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Single crystals of the title new cyclohexaphosphate, 6C7H8Cl2N+·P6O186-·6H2O, were synthesized and investigated by X-ray diffraction. The phosphate rings are centrosymmetric. The asymmetric unit consists of three cations, one half-anion and three water molecules. The three-dimensional network is built up from parallel layers of anionic P6O18 rings and water molecules, between which the organic molecules are inserted. The 3,4-dichlorobenzylamine exercises an electrostatic interaction with the inorganic anions and establishes strong hydrogen bonds with the O atoms of the ring and the water molecules.
Supporting information
CCDC reference: 647723
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.046
- wR factor = 0.122
- Data-to-parameter ratio = 18.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O6
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C1
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C8
PLAT432_ALERT_2_C Short Inter X...Y Contact O10 .. C1 .. 2.99 Ang.
PLAT731_ALERT_1_C Bond Calc 0.82(4), Rep 0.821(19) ...... 2.11 su-Ra
O10 -H10B 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.80(4), Rep 0.802(19) ...... 2.11 su-Ra
O12 -H12A 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.82(4), Rep 0.821(19) ...... 2.11 su-Ra
O10 -H10B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.80(4), Rep 0.802(19) ...... 2.11 su-Ra
O12 -H12A 1.555 1.555
Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
10 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
7 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
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
checkCIF publication errors
Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 159
Cs~6~P~6~O~18~.6~H~2~O, which shows the greatest distortion for the same angles
If you require a ~ then it should be escaped
with a \, i.e. \~
Otherwise there must be a matching closing ~, e.g. C~2~H~4~
1 ALERT level A = Data missing that is essential or data in wrong format
0 ALERT level G = General alerts. Data that may be required is missing
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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 (Farrugia, 1999).
Hexakis(3,4-dichlorobenzylammonium) cyclohexaphosphate hexahydrate
top
Crystal data top
6C7H8Cl2N+·O18P66−·6H2O | F(000) = 1680 |
Mr = 1644.18 | Dx = 1.66 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 8608 reflections |
a = 19.384 (3) Å | θ = 2.1–28.0° |
b = 11.788 (5) Å | µ = 0.73 mm−1 |
c = 15.447 (3) Å | T = 293 K |
β = 111.230 (18)° | Plate, colourless |
V = 3290.1 (16) Å3 | 0.7 × 0.4 × 0.2 mm |
Z = 2 | |
Data collection top
Enraf–Nonius TurboCAD-4 diffractometer | 5615 reflections with I > 2σ(I) |
Radiation source: Enraf–Nonius FR590 | Rint = 0.020 |
Graphite monochromator | θmax = 28.0°, θmin = 2.1° |
ω/2θ scans | h = −1→25 |
Absorption correction: multi-scan (Blessing, 1995) | k = −15→0 |
Tmin = 0.774, Tmax = 0.864 | l = −20→19 |
8608 measured reflections | 2 standard reflections every 120 min |
7921 independent reflections | intensity decay: 4% |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0619P)2 + 1.4475P] where P = (Fo2 + 2Fc2)/3 |
7921 reflections | (Δ/σ)max = 0.001 |
427 parameters | Δρmax = 0.59 e Å−3 |
6 restraints | Δρmin = −0.66 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 | Uiso*/Ueq | |
Cl1 | 0.82491 (6) | 0.79503 (10) | 0.64378 (6) | 0.0710 (3) | |
Cl2 | 0.96557 (6) | 0.69200 (9) | 0.80180 (10) | 0.0806 (3) | |
Cl3 | 0.10446 (5) | 0.96752 (10) | 0.52322 (6) | 0.0694 (3) | |
Cl4 | 0.02734 (5) | 0.86347 (8) | 0.65294 (8) | 0.0672 (3) | |
Cl5 | 0.02634 (4) | 0.95724 (8) | 0.13525 (7) | 0.0588 (2) | |
Cl6 | 0.11127 (5) | 0.85927 (9) | 0.01137 (6) | 0.0651 (3) | |
P1 | 0.50272 (3) | 0.23621 (5) | 0.04888 (4) | 0.02421 (14) | |
P2 | 0.51134 (4) | 0.41684 (5) | 0.18644 (4) | 0.02639 (15) | |
P3 | 0.56851 (4) | 0.61235 (5) | 0.11206 (4) | 0.02523 (14) | |
O1 | 0.44699 (11) | 0.14518 (16) | 0.01558 (13) | 0.0368 (4) | |
O2 | 0.58257 (10) | 0.20482 (15) | 0.08867 (13) | 0.0337 (4) | |
O3 | 0.47972 (9) | 0.30736 (14) | 0.12199 (11) | 0.0272 (4) | |
O4 | 0.58079 (12) | 0.38977 (18) | 0.26365 (13) | 0.0437 (5) | |
O5 | 0.44736 (12) | 0.46175 (16) | 0.20682 (14) | 0.0406 (5) | |
O6 | 0.52620 (12) | 0.49621 (16) | 0.11151 (12) | 0.0428 (5) | |
O7 | 0.62998 (10) | 0.58708 (17) | 0.07977 (13) | 0.0378 (4) | |
O8 | 0.58339 (12) | 0.67410 (17) | 0.19997 (12) | 0.0406 (5) | |
O9 | 0.50273 (10) | 0.67517 (15) | 0.03167 (11) | 0.0306 (4) | |
O10 | 0.36294 (16) | 0.9097 (2) | 0.04153 (17) | 0.0608 (7) | |
H10A | 0.392 (2) | 0.898 (4) | 0.0958 (17) | 0.091* | |
H10B | 0.395 (2) | 0.887 (4) | 0.023 (3) | 0.091* | |
O11 | 0.68486 (12) | 0.8775 (2) | 0.44148 (15) | 0.0474 (5) | |
H11A | 0.671 (2) | 0.877 (4) | 0.486 (2) | 0.071* | |
H11B | 0.6484 (16) | 0.899 (3) | 0.397 (2) | 0.071* | |
O12 | 0.37390 (13) | 0.8327 (2) | 0.65853 (16) | 0.0497 (5) | |
H12A | 0.4062 (18) | 0.877 (3) | 0.685 (3) | 0.075* | |
H12B | 0.390 (2) | 0.772 (2) | 0.685 (3) | 0.075* | |
N1 | 0.66006 (13) | 0.8525 (2) | 0.88456 (15) | 0.0362 (5) | |
H1A | 0.6344 | 0.8454 | 0.824 | 0.054* | |
H1B | 0.6321 | 0.8861 | 0.9118 | 0.054* | |
H1C | 0.6736 | 0.7842 | 0.9095 | 0.054* | |
N2 | 0.39250 (12) | 1.02837 (19) | 0.85057 (15) | 0.0332 (5) | |
H2A | 0.3829 | 0.9559 | 0.8578 | 0.05* | |
H2B | 0.4222 | 1.0565 | 0.9047 | 0.05* | |
H2C | 0.4145 | 1.0337 | 0.8092 | 0.05* | |
N3 | 0.33262 (12) | 0.8667 (2) | 0.46633 (15) | 0.0351 (5) | |
H3A | 0.3536 | 0.814 | 0.4427 | 0.053* | |
H3B | 0.3492 | 0.86 | 0.5279 | 0.053* | |
H3C | 0.3439 | 0.9352 | 0.4512 | 0.053* | |
C1 | 0.72653 (19) | 0.9220 (3) | 0.8985 (3) | 0.0569 (9) | |
H1D | 0.7476 | 0.9448 | 0.9632 | 0.068* | |
H1E | 0.712 | 0.9903 | 0.8613 | 0.068* | |
C2 | 0.78506 (16) | 0.8615 (2) | 0.8732 (2) | 0.0376 (6) | |
C3 | 0.77862 (16) | 0.8518 (2) | 0.78115 (19) | 0.0366 (6) | |
H3 | 0.7369 | 0.8799 | 0.7342 | 0.044* | |
C4 | 0.83432 (16) | 0.8004 (2) | 0.75938 (19) | 0.0372 (6) | |
C5 | 0.89619 (16) | 0.7575 (3) | 0.8283 (2) | 0.0430 (7) | |
C6 | 0.90271 (18) | 0.7681 (3) | 0.9197 (2) | 0.0540 (9) | |
H6 | 0.9443 | 0.7398 | 0.9667 | 0.065* | |
C7 | 0.84784 (19) | 0.8202 (3) | 0.9413 (2) | 0.0520 (8) | |
H7 | 0.8531 | 0.8279 | 1.0033 | 0.062* | |
C8 | 0.32225 (18) | 1.0934 (3) | 0.8173 (3) | 0.0641 (11) | |
H8A | 0.3245 | 1.1475 | 0.7711 | 0.077* | |
H8B | 0.3188 | 1.1365 | 0.8691 | 0.077* | |
C9 | 0.25277 (16) | 1.0248 (2) | 0.7759 (2) | 0.0399 (7) | |
C10 | 0.21687 (16) | 1.0202 (3) | 0.6808 (2) | 0.0398 (6) | |
H10 | 0.2388 | 1.0523 | 0.6421 | 0.048* | |
C11 | 0.14868 (16) | 0.9682 (3) | 0.64270 (19) | 0.0376 (6) | |
C12 | 0.11503 (16) | 0.9209 (2) | 0.6990 (2) | 0.0404 (7) | |
C13 | 0.1515 (2) | 0.9211 (3) | 0.7929 (2) | 0.0516 (8) | |
H13 | 0.1301 | 0.8865 | 0.8311 | 0.062* | |
C14 | 0.2199 (2) | 0.9723 (3) | 0.8316 (2) | 0.0525 (8) | |
H14 | 0.2442 | 0.9717 | 0.8958 | 0.063* | |
C15 | 0.25128 (16) | 0.8516 (3) | 0.4283 (2) | 0.0454 (7) | |
H15A | 0.2287 | 0.9103 | 0.4533 | 0.054* | |
H15B | 0.2392 | 0.7789 | 0.4486 | 0.054* | |
C16 | 0.21875 (15) | 0.8566 (2) | 0.32373 (19) | 0.0365 (6) | |
C17 | 0.14788 (15) | 0.9001 (2) | 0.2814 (2) | 0.0375 (6) | |
H17 | 0.1228 | 0.929 | 0.3177 | 0.045* | |
C18 | 0.11420 (15) | 0.9009 (2) | 0.1853 (2) | 0.0383 (6) | |
C19 | 0.15147 (16) | 0.8587 (3) | 0.13137 (19) | 0.0395 (6) | |
C20 | 0.22193 (16) | 0.8154 (3) | 0.1727 (2) | 0.0421 (7) | |
H20 | 0.2469 | 0.7868 | 0.1361 | 0.05* | |
C21 | 0.25576 (16) | 0.8142 (3) | 0.2687 (2) | 0.0407 (7) | |
H21 | 0.3033 | 0.7851 | 0.2963 | 0.049* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0946 (7) | 0.0868 (7) | 0.0428 (4) | −0.0039 (6) | 0.0384 (5) | −0.0132 (5) |
Cl2 | 0.0657 (6) | 0.0672 (6) | 0.1304 (10) | 0.0178 (5) | 0.0615 (7) | 0.0119 (6) |
Cl3 | 0.0651 (6) | 0.1007 (8) | 0.0321 (4) | 0.0024 (5) | 0.0052 (4) | −0.0021 (4) |
Cl4 | 0.0407 (4) | 0.0608 (6) | 0.0948 (7) | −0.0113 (4) | 0.0182 (5) | 0.0021 (5) |
Cl5 | 0.0401 (4) | 0.0598 (5) | 0.0666 (5) | 0.0126 (4) | 0.0075 (4) | 0.0137 (4) |
Cl6 | 0.0660 (6) | 0.0836 (7) | 0.0350 (4) | 0.0059 (5) | 0.0053 (4) | 0.0059 (4) |
P1 | 0.0288 (3) | 0.0215 (3) | 0.0224 (3) | −0.0010 (2) | 0.0093 (2) | −0.0014 (2) |
P2 | 0.0375 (4) | 0.0229 (3) | 0.0188 (3) | −0.0026 (3) | 0.0103 (3) | 0.0009 (2) |
P3 | 0.0329 (3) | 0.0236 (3) | 0.0183 (3) | −0.0041 (3) | 0.0083 (2) | −0.0009 (2) |
O1 | 0.0461 (11) | 0.0333 (10) | 0.0337 (9) | −0.0141 (9) | 0.0176 (8) | −0.0113 (8) |
O2 | 0.0349 (10) | 0.0293 (9) | 0.0356 (10) | 0.0051 (8) | 0.0113 (8) | 0.0024 (8) |
O3 | 0.0351 (9) | 0.0242 (8) | 0.0256 (8) | −0.0039 (7) | 0.0151 (7) | −0.0028 (7) |
O4 | 0.0479 (12) | 0.0454 (12) | 0.0278 (9) | −0.0018 (10) | 0.0016 (9) | 0.0013 (9) |
O5 | 0.0549 (12) | 0.0316 (10) | 0.0428 (11) | 0.0031 (9) | 0.0267 (10) | −0.0057 (9) |
O6 | 0.0710 (14) | 0.0330 (10) | 0.0220 (9) | −0.0233 (10) | 0.0140 (9) | −0.0002 (8) |
O7 | 0.0373 (10) | 0.0427 (11) | 0.0347 (10) | 0.0035 (9) | 0.0145 (8) | 0.0036 (8) |
O8 | 0.0560 (12) | 0.0372 (11) | 0.0244 (9) | −0.0052 (9) | 0.0095 (9) | −0.0088 (8) |
O9 | 0.0328 (9) | 0.0360 (10) | 0.0244 (8) | 0.0021 (8) | 0.0120 (7) | 0.0070 (7) |
O10 | 0.0798 (19) | 0.0635 (16) | 0.0425 (13) | 0.0291 (14) | 0.0262 (13) | 0.0072 (12) |
O11 | 0.0451 (12) | 0.0602 (15) | 0.0402 (12) | −0.0026 (11) | 0.0195 (10) | −0.0044 (11) |
O12 | 0.0570 (14) | 0.0403 (13) | 0.0437 (12) | −0.0073 (11) | 0.0086 (11) | 0.0040 (10) |
N1 | 0.0404 (13) | 0.0448 (13) | 0.0276 (11) | 0.0000 (11) | 0.0176 (10) | 0.0000 (10) |
N2 | 0.0375 (12) | 0.0317 (12) | 0.0282 (11) | −0.0044 (10) | 0.0094 (9) | −0.0019 (9) |
N3 | 0.0365 (12) | 0.0354 (12) | 0.0312 (11) | −0.0004 (10) | 0.0097 (9) | −0.0004 (10) |
C1 | 0.061 (2) | 0.0484 (19) | 0.077 (2) | −0.0149 (17) | 0.045 (2) | −0.0250 (18) |
C2 | 0.0421 (15) | 0.0366 (15) | 0.0409 (15) | −0.0119 (12) | 0.0231 (13) | −0.0073 (12) |
C3 | 0.0374 (15) | 0.0364 (15) | 0.0341 (14) | −0.0006 (12) | 0.0105 (12) | −0.0009 (12) |
C4 | 0.0441 (16) | 0.0364 (15) | 0.0352 (14) | −0.0054 (12) | 0.0192 (12) | −0.0043 (12) |
C5 | 0.0374 (15) | 0.0367 (15) | 0.0610 (19) | −0.0011 (13) | 0.0251 (14) | 0.0037 (14) |
C6 | 0.0401 (17) | 0.064 (2) | 0.0504 (18) | 0.0007 (16) | 0.0074 (14) | 0.0221 (17) |
C7 | 0.056 (2) | 0.069 (2) | 0.0335 (15) | −0.0158 (17) | 0.0192 (14) | 0.0028 (15) |
C8 | 0.0446 (18) | 0.0356 (17) | 0.089 (3) | 0.0017 (15) | −0.0031 (18) | −0.0134 (18) |
C9 | 0.0377 (15) | 0.0311 (14) | 0.0426 (16) | 0.0027 (12) | 0.0046 (12) | −0.0043 (12) |
C10 | 0.0395 (15) | 0.0390 (16) | 0.0426 (16) | 0.0014 (13) | 0.0168 (13) | 0.0039 (13) |
C11 | 0.0373 (15) | 0.0406 (15) | 0.0321 (13) | 0.0027 (12) | 0.0093 (11) | −0.0009 (12) |
C12 | 0.0349 (15) | 0.0371 (15) | 0.0496 (17) | −0.0002 (12) | 0.0156 (13) | −0.0003 (13) |
C13 | 0.059 (2) | 0.059 (2) | 0.0446 (17) | 0.0036 (17) | 0.0286 (16) | 0.0114 (15) |
C14 | 0.062 (2) | 0.059 (2) | 0.0288 (15) | 0.0073 (17) | 0.0064 (14) | −0.0038 (14) |
C15 | 0.0351 (15) | 0.065 (2) | 0.0372 (15) | −0.0043 (14) | 0.0149 (12) | 0.0020 (14) |
C16 | 0.0331 (14) | 0.0390 (15) | 0.0374 (14) | −0.0050 (12) | 0.0128 (12) | 0.0021 (12) |
C17 | 0.0337 (14) | 0.0378 (15) | 0.0426 (15) | −0.0012 (12) | 0.0156 (12) | 0.0007 (12) |
C18 | 0.0319 (14) | 0.0327 (14) | 0.0456 (16) | 0.0001 (11) | 0.0081 (12) | 0.0085 (12) |
C19 | 0.0413 (15) | 0.0386 (15) | 0.0333 (14) | −0.0031 (13) | 0.0071 (12) | 0.0049 (12) |
C20 | 0.0406 (15) | 0.0505 (18) | 0.0353 (14) | 0.0007 (14) | 0.0140 (12) | −0.0010 (13) |
C21 | 0.0315 (14) | 0.0518 (18) | 0.0376 (15) | 0.0057 (13) | 0.0112 (12) | 0.0067 (13) |
Geometric parameters (Å, º) top
Cl1—C4 | 1.729 (3) | C1—C2 | 1.506 (4) |
Cl2—C5 | 1.724 (3) | C1—H1D | 0.97 |
Cl3—C11 | 1.731 (3) | C1—H1E | 0.97 |
Cl4—C12 | 1.726 (3) | C2—C7 | 1.378 (5) |
Cl5—C18 | 1.728 (3) | C2—C3 | 1.387 (4) |
Cl6—C19 | 1.731 (3) | C3—C4 | 1.382 (4) |
P1—O1 | 1.4766 (19) | C3—H3 | 0.93 |
P1—O2 | 1.4905 (19) | C4—C5 | 1.380 (4) |
P1—O3 | 1.5945 (17) | C5—C6 | 1.377 (5) |
P1—O9i | 1.5986 (18) | C6—C7 | 1.371 (5) |
P2—O4 | 1.474 (2) | C6—H6 | 0.93 |
P2—O5 | 1.483 (2) | C7—H7 | 0.93 |
P2—O6 | 1.5937 (19) | C8—C9 | 1.501 (4) |
P2—O3 | 1.6095 (18) | C8—H8A | 0.97 |
P3—O8 | 1.4743 (18) | C8—H8B | 0.97 |
P3—O7 | 1.479 (2) | C9—C10 | 1.380 (4) |
P3—O6 | 1.5943 (19) | C9—C14 | 1.389 (5) |
P3—O9 | 1.6029 (18) | C10—C11 | 1.380 (4) |
O9—P1i | 1.5986 (18) | C10—H10 | 0.93 |
O10—H10A | 0.833 (19) | C11—C12 | 1.379 (4) |
O10—H10B | 0.821 (19) | C12—C13 | 1.365 (4) |
O11—H11A | 0.833 (18) | C13—C14 | 1.380 (5) |
O11—H11B | 0.827 (18) | C13—H13 | 0.93 |
O12—H12A | 0.802 (19) | C14—H14 | 0.93 |
O12—H12B | 0.825 (18) | C15—C16 | 1.508 (4) |
N1—C1 | 1.475 (4) | C15—H15A | 0.97 |
N1—H1A | 0.89 | C15—H15B | 0.97 |
N1—H1B | 0.89 | C16—C17 | 1.388 (4) |
N1—H1C | 0.89 | C16—C21 | 1.388 (4) |
N2—C8 | 1.483 (4) | C17—C18 | 1.389 (4) |
N2—H2A | 0.89 | C17—H17 | 0.93 |
N2—H2B | 0.89 | C18—C19 | 1.378 (4) |
N2—H2C | 0.89 | C19—C20 | 1.379 (4) |
N3—C15 | 1.480 (4) | C20—C21 | 1.387 (4) |
N3—H3A | 0.89 | C20—H20 | 0.93 |
N3—H3B | 0.89 | C21—H21 | 0.93 |
N3—H3C | 0.89 | | |
| | | |
O1—P1—O2 | 118.86 (12) | C6—C5—C4 | 119.3 (3) |
O1—P1—O3 | 105.79 (10) | C6—C5—Cl2 | 119.6 (3) |
O2—P1—O3 | 110.69 (10) | C4—C5—Cl2 | 121.1 (2) |
O1—P1—O9i | 111.72 (11) | C7—C6—C5 | 120.0 (3) |
O2—P1—O9i | 104.44 (10) | C7—C6—H6 | 120 |
O3—P1—O9i | 104.53 (10) | C5—C6—H6 | 120 |
O4—P2—O5 | 119.62 (12) | C6—C7—C2 | 121.4 (3) |
O4—P2—O6 | 111.24 (12) | C6—C7—H7 | 119.3 |
O5—P2—O6 | 109.24 (12) | C2—C7—H7 | 119.3 |
O4—P2—O3 | 111.00 (11) | N2—C8—C9 | 116.0 (3) |
O5—P2—O3 | 104.90 (11) | N2—C8—H8A | 108.3 |
O6—P2—O3 | 98.62 (10) | C9—C8—H8A | 108.3 |
O8—P3—O7 | 119.82 (12) | N2—C8—H8B | 108.3 |
O8—P3—O6 | 110.95 (11) | C9—C8—H8B | 108.3 |
O7—P3—O6 | 107.51 (12) | H8A—C8—H8B | 107.4 |
O8—P3—O9 | 108.72 (11) | C10—C9—C14 | 118.3 (3) |
O7—P3—O9 | 110.11 (10) | C10—C9—C8 | 120.2 (3) |
O6—P3—O9 | 97.43 (11) | C14—C9—C8 | 121.2 (3) |
P1—O3—P2 | 135.93 (11) | C11—C10—C9 | 120.5 (3) |
P2—O6—P3 | 136.74 (12) | C11—C10—H10 | 119.8 |
P1i—O9—P3 | 135.61 (12) | C9—C10—H10 | 119.8 |
H10A—O10—H10B | 89 (4) | C12—C11—C10 | 120.6 (3) |
H11A—O11—H11B | 104 (4) | C12—C11—Cl3 | 120.4 (2) |
H12A—O12—H12B | 102 (4) | C10—C11—Cl3 | 119.0 (2) |
C1—N1—H1A | 109.5 | C13—C12—C11 | 119.2 (3) |
C1—N1—H1B | 109.5 | C13—C12—Cl4 | 119.5 (3) |
H1A—N1—H1B | 109.5 | C11—C12—Cl4 | 121.3 (2) |
C1—N1—H1C | 109.5 | C12—C13—C14 | 120.6 (3) |
H1A—N1—H1C | 109.5 | C12—C13—H13 | 119.7 |
H1B—N1—H1C | 109.5 | C14—C13—H13 | 119.7 |
C8—N2—H2A | 109.5 | C13—C14—C9 | 120.7 (3) |
C8—N2—H2B | 109.5 | C13—C14—H14 | 119.7 |
H2A—N2—H2B | 109.5 | C9—C14—H14 | 119.7 |
C8—N2—H2C | 109.5 | N3—C15—C16 | 113.1 (2) |
H2A—N2—H2C | 109.5 | N3—C15—H15A | 109 |
H2B—N2—H2C | 109.5 | C16—C15—H15A | 109 |
C15—N3—H3A | 109.5 | N3—C15—H15B | 109 |
C15—N3—H3B | 109.5 | C16—C15—H15B | 109 |
H3A—N3—H3B | 109.5 | H15A—C15—H15B | 107.8 |
C15—N3—H3C | 109.5 | C17—C16—C21 | 119.2 (3) |
H3A—N3—H3C | 109.5 | C17—C16—C15 | 118.5 (3) |
H3B—N3—H3C | 109.5 | C21—C16—C15 | 122.2 (3) |
N1—C1—C2 | 113.5 (2) | C16—C17—C18 | 120.5 (3) |
N1—C1—H1D | 108.9 | C16—C17—H17 | 119.8 |
C2—C1—H1D | 108.9 | C18—C17—H17 | 119.8 |
N1—C1—H1E | 108.9 | C19—C18—C17 | 119.8 (3) |
C2—C1—H1E | 108.9 | C19—C18—Cl5 | 121.1 (2) |
H1D—C1—H1E | 107.7 | C17—C18—Cl5 | 119.1 (2) |
C7—C2—C3 | 118.7 (3) | C18—C19—C20 | 120.1 (3) |
C7—C2—C1 | 120.6 (3) | C18—C19—Cl6 | 121.0 (2) |
C3—C2—C1 | 120.6 (3) | C20—C19—Cl6 | 118.9 (2) |
C4—C3—C2 | 119.9 (3) | C19—C20—C21 | 120.3 (3) |
C4—C3—H3 | 120.1 | C19—C20—H20 | 119.9 |
C2—C3—H3 | 120.1 | C21—C20—H20 | 119.9 |
C5—C4—C3 | 120.7 (3) | C20—C21—C16 | 120.1 (3) |
C5—C4—Cl1 | 121.4 (2) | C20—C21—H21 | 119.9 |
C3—C4—Cl1 | 117.9 (2) | C16—C21—H21 | 119.9 |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O10—H10A···O4ii | 0.83 (2) | 2.04 (3) | 2.815 (3) | 154 (5) |
O10—H10B···O2i | 0.82 (2) | 2.21 (3) | 2.919 (3) | 145 (4) |
O11—H11A···O7iii | 0.83 (2) | 1.93 (2) | 2.742 (3) | 166 (4) |
O11—H11B···O5ii | 0.83 (2) | 2.10 (2) | 2.924 (3) | 175 (4) |
O12—H12A···O5iii | 0.80 (2) | 2.05 (3) | 2.773 (3) | 151 (4) |
O12—H12B···O4iv | 0.83 (2) | 2.07 (2) | 2.886 (3) | 172 (4) |
N1—H1A···O8iii | 0.89 | 1.82 | 2.715 (3) | 178 |
N1—H1B···O1iv | 0.89 | 2.23 | 3.001 (3) | 144 |
N1—H1C···O11iii | 0.89 | 1.96 | 2.837 (4) | 168 |
N2—H2A···O2iv | 0.89 | 2.08 | 2.888 (3) | 151 |
N2—H2B···O1v | 0.89 | 1.91 | 2.749 (3) | 156 |
N2—H2C···O5iii | 0.89 | 1.91 | 2.790 (3) | 171 |
N3—H3A···O2ii | 0.89 | 1.96 | 2.842 (3) | 169 |
N3—H3B···O12 | 0.89 | 1.93 | 2.810 (3) | 172 |
N3—H3C···O7ii | 0.89 | 1.97 | 2.856 (3) | 179 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, y+1/2, −z+1/2; (iii) x, −y+3/2, z+1/2; (iv) −x+1, −y+1, −z+1; (v) x, y+1, z+1. |
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