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In the title compound, 2C10H9N2+·2C9H6SO4-·C10H8N2·5H2O, the asymmetric unit contains two 8-hydroxyquinoline-5-sulfonate (HQS) anions, two 4,4'-bipyridinium ions, a neutral 4,4'-bipyridine molecule and five water molecules. The sulfonic acid group is deprotonated. Interestingly, in both the HQS anions, the O-H bond is oriented away from the quinoline-N atom, since the water molecule competes in hydrogen bonding with the quinolinol-O atom. The neutral 4,4'-bipyridine and one of the protonated 4,4'-bipyridine moieties are bridged by two water molecules, resulting in a `U'-shaped hydrogen-bonded molecular arrangement. Many stacking interactions were observed between: (i) the pyridine rings of bipyridine moieties; (ii) the pyridine rings of bipyridine and HQS moieties; (iii) the pyridine ring of bipyridine and the benzene ring of the HQS anion.
Supporting information
CCDC reference: 200583
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.061
- wR factor = 0.174
- Data-to-parameter ratio = 17.6
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ....... 0.85
Alert level B
REFLT03_ALERT_3_B Reflection count < 90% complete (theta max?)
From the CIF: _diffrn_reflns_theta_max 30.45
From the CIF: _diffrn_reflns_theta_full 0.00
From the CIF: _reflns_number_total 12128
TEST2: Reflns within _diffrn_reflns_theta_max
Count of symmetry unique reflns 14245
Completeness (_total/calc) 85.14%
Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ?
PLAT213_ALERT_2_C Atom O4 has ADP max/min Ratio ............. 3.40 prolat
PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... S2
PLAT250_ALERT_2_C Large U3/U1 ratio for average U(i,j) tensor .... 2.07
PLAT417_ALERT_2_C Short Inter D-H..H-D H21 .. H31 = 2.12 Ang.
Alert level G
FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the
_chemical_formula_sum and _chemical_formula_moiety. This is
usually due to the moiety formula being in the wrong format.
Atom count from _chemical_formula_sum: C48 H48 N8 O13 S2
Atom count from _chemical_formula_moiety:C48 H48 N6 O13 S2
ABSTY01_ALERT_1_G Extra text has been found in the _exptl_absorpt_correction_type
field, which should be only a single keyword. A literature
citation should be included in the _exptl_absorpt_process_details
field.
1 ALERT level A = In general: serious problem
1 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
2 ALERT level G = General alerts; check
3 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
2 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SMART (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1997); software used to prepare material for publication: PLATON (Spek, 1997).
Bis(4,4'-bipyridinium) bis(8-hydroxyquinoline-5-sulfonate) bipyridine
pentahydrate
top
Crystal data top
2C10H9N2+·2C9H6SO4−·C10H8N2·5H2O | Z = 2 |
Mr = 1009.08 | F(000) = 1056 |
Triclinic, P1 | Dx = 1.432 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71069 Å |
a = 9.449 (3) Å | Cell parameters from 50 reflections |
b = 14.330 (2) Å | θ = 1.1–30.5° |
c = 19.449 (3) Å | µ = 0.19 mm−1 |
α = 111.080 (2)° | T = 293 K |
β = 93.730 (3)° | Thin plate, pale yellow |
γ = 104.770 (2)° | 0.33 × 0.31 × 0.21 mm |
V = 2339.9 (9) Å3 | |
Data collection top
Bruker AXS SMART CCD diffractometer | 12128 independent reflections |
Radiation source: fine-focus sealed tube | 7325 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.055 |
ω scans | θmax = 30.5°, θmin = 1.1° |
Absorption correction: ψ scan corrections (north et al., 1968) | h = −13→13 |
Tmin = 0.921, Tmax = 0.958 | k = −20→20 |
29740 measured reflections | l = −27→27 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 0.98 | w = 1/[σ2(Fo2) + (0.0967P)2] where P = (Fo2 + 2Fc2)/3 |
12128 reflections | (Δ/σ)max = 0.001 |
688 parameters | Δρmax = 0.44 e Å−3 |
0 restraints | Δρmin = −0.46 e Å−3 |
Special details top
Geometry. Bond distances, angles etc. have been calculated using the rounded
fractional coordinates. All e.s.d.'s are estimated from the variances of the
(full) variance-covariance matrix. The cell e.s.d.'s are taken into account in
the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user
for potential systematic errors. Weighted R-factors wR
and all goodnesses of fit S are based on F2,
conventional R-factors R are based on F, with F
set to zero for negative F2. The observed criterion of F2 >
σ(F2) is used only for calculating -R-factor-obs
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 | |
S1 | −0.08802 (6) | 0.55174 (4) | 0.14356 (3) | 0.0479 (2) | |
O11 | 0.51174 (17) | 0.77037 (13) | 0.32962 (8) | 0.0583 (5) | |
O12 | −0.18944 (17) | 0.55922 (15) | 0.19616 (10) | 0.0692 (6) | |
O13 | −0.10310 (19) | 0.60925 (14) | 0.09731 (10) | 0.0668 (6) | |
O14 | −0.09299 (18) | 0.44474 (13) | 0.10130 (10) | 0.0673 (6) | |
N11 | 0.49106 (19) | 0.67127 (14) | 0.18383 (9) | 0.0471 (5) | |
C12 | 0.4823 (3) | 0.62341 (19) | 0.11101 (12) | 0.0530 (7) | |
C13 | 0.3488 (3) | 0.57188 (18) | 0.06086 (12) | 0.0518 (7) | |
C14 | 0.2186 (2) | 0.56787 (16) | 0.08697 (11) | 0.0453 (6) | |
C15 | 0.0918 (2) | 0.61291 (15) | 0.19873 (10) | 0.0393 (6) | |
C16 | 0.1077 (2) | 0.66059 (17) | 0.27491 (11) | 0.0447 (6) | |
C17 | 0.2466 (2) | 0.71318 (17) | 0.32036 (11) | 0.0476 (7) | |
C18 | 0.3734 (2) | 0.71873 (16) | 0.29016 (11) | 0.0441 (6) | |
C19 | 0.3611 (2) | 0.66737 (15) | 0.21120 (10) | 0.0395 (6) | |
C20 | 0.2210 (2) | 0.61566 (15) | 0.16469 (10) | 0.0386 (6) | |
S2 | 0.98847 (8) | 0.31396 (5) | 0.51018 (3) | 0.0617 (2) | |
O1 | 0.8201 (2) | 0.04259 (13) | 0.18642 (8) | 0.0615 (6) | |
O2 | 0.87018 (19) | 0.35952 (13) | 0.52746 (9) | 0.0633 (6) | |
O3 | 1.1290 (2) | 0.39217 (18) | 0.52050 (11) | 0.0933 (7) | |
O4 | 0.9945 (4) | 0.2435 (2) | 0.54667 (11) | 0.1427 (15) | |
N1 | 0.85851 (19) | 0.24540 (14) | 0.22730 (9) | 0.0463 (6) | |
C2 | 0.8748 (2) | 0.34629 (18) | 0.24739 (12) | 0.0502 (7) | |
C3 | 0.9136 (2) | 0.41810 (17) | 0.32126 (12) | 0.0501 (7) | |
C4 | 0.9374 (2) | 0.38438 (16) | 0.37713 (11) | 0.0434 (6) | |
C5 | 0.9426 (2) | 0.23357 (16) | 0.41305 (10) | 0.0424 (6) | |
C6 | 0.9248 (2) | 0.12858 (17) | 0.38915 (12) | 0.0470 (7) | |
C7 | 0.8848 (2) | 0.06166 (16) | 0.31279 (11) | 0.0461 (7) | |
C8 | 0.8617 (2) | 0.10114 (16) | 0.26027 (11) | 0.0435 (6) | |
C9 | 0.8809 (2) | 0.20997 (15) | 0.28247 (10) | 0.0388 (5) | |
C10 | 0.92134 (19) | 0.27743 (15) | 0.35939 (10) | 0.0378 (5) | |
N1B | 0.2922 (3) | 0.84029 (15) | 0.13407 (11) | 0.0609 (7) | |
N10B | 0.4608 (2) | 1.12925 (17) | 0.52148 (10) | 0.0613 (7) | |
C2B | 0.1825 (3) | 0.8504 (2) | 0.17184 (14) | 0.0655 (8) | |
C3B | 0.2112 (3) | 0.9051 (2) | 0.24763 (14) | 0.0592 (8) | |
C4B | 0.3565 (2) | 0.94959 (16) | 0.28610 (12) | 0.0467 (6) | |
C5B | 0.4682 (3) | 0.93484 (19) | 0.24435 (12) | 0.0562 (8) | |
C6B | 0.4324 (3) | 0.8805 (2) | 0.16829 (13) | 0.0614 (8) | |
C7B | 0.3919 (2) | 1.00968 (17) | 0.36770 (12) | 0.0473 (6) | |
C8B | 0.2890 (3) | 0.9995 (2) | 0.41313 (13) | 0.0591 (8) | |
C9B | 0.3273 (3) | 1.0602 (2) | 0.48907 (13) | 0.0638 (9) | |
C11B | 0.5597 (3) | 1.1392 (2) | 0.47761 (13) | 0.0636 (8) | |
C12B | 0.5308 (3) | 1.0822 (2) | 0.40154 (12) | 0.0568 (7) | |
N1C | 0.2748 (3) | 0.27625 (16) | 0.01168 (11) | 0.0631 (7) | |
N10C | 0.4667 (2) | 0.56297 (17) | 0.39941 (11) | 0.0587 (7) | |
C2C | 0.1753 (3) | 0.3063 (2) | 0.05218 (14) | 0.0634 (8) | |
C3C | 0.2084 (3) | 0.36246 (19) | 0.12848 (13) | 0.0552 (8) | |
C4C | 0.3519 (2) | 0.39191 (16) | 0.16586 (11) | 0.0442 (6) | |
C5C | 0.4570 (3) | 0.3626 (2) | 0.12355 (13) | 0.0558 (8) | |
C6C | 0.4121 (3) | 0.3045 (2) | 0.04785 (14) | 0.0634 (9) | |
C7C | 0.3927 (2) | 0.45253 (16) | 0.24789 (11) | 0.0437 (6) | |
C8C | 0.2887 (3) | 0.4480 (2) | 0.29377 (13) | 0.0590 (8) | |
C9C | 0.3272 (3) | 0.5046 (2) | 0.36902 (14) | 0.0655 (9) | |
C11C | 0.5713 (3) | 0.5698 (2) | 0.35748 (13) | 0.0580 (8) | |
C12C | 0.5369 (3) | 0.51594 (19) | 0.28148 (13) | 0.0531 (7) | |
N1A | 0.2765 (4) | 0.0508 (2) | 0.05903 (14) | 0.0871 (10) | |
N10A | 0.4666 (2) | 0.33599 (18) | 0.44927 (11) | 0.0606 (7) | |
C2A | 0.1771 (4) | 0.0791 (3) | 0.09962 (18) | 0.0894 (11) | |
C3A | 0.2095 (3) | 0.1351 (2) | 0.17561 (16) | 0.0745 (10) | |
C4A | 0.3522 (3) | 0.16351 (18) | 0.21337 (13) | 0.0505 (7) | |
C5A | 0.4571 (3) | 0.1350 (2) | 0.17111 (15) | 0.0674 (9) | |
C6A | 0.4127 (4) | 0.0795 (3) | 0.09543 (17) | 0.0837 (13) | |
C7A | 0.3917 (2) | 0.22305 (17) | 0.29524 (12) | 0.0476 (7) | |
C8A | 0.2900 (3) | 0.2127 (2) | 0.34193 (14) | 0.0586 (8) | |
C9A | 0.3316 (3) | 0.2695 (2) | 0.41713 (14) | 0.0638 (9) | |
C11A | 0.5650 (3) | 0.3463 (2) | 0.40546 (14) | 0.0634 (8) | |
C12A | 0.5329 (3) | 0.2921 (2) | 0.32938 (14) | 0.0589 (8) | |
O1W | 0.0731 (2) | 0.10775 (17) | 0.60475 (13) | 0.0826 (8) | |
O2W | 0.8154 (5) | 0.1331 (2) | 0.06996 (13) | 0.1525 (18) | |
O3W | 0.7415 (2) | 0.25135 (15) | 0.00975 (10) | 0.0804 (7) | |
O4W | 0.8191 (3) | 0.85004 (15) | 0.14037 (11) | 0.0915 (8) | |
O5W | 0.78772 (19) | 0.76679 (15) | 0.24697 (10) | 0.0689 (6) | |
H11' | 0.50840 | 0.79170 | 0.37440 | 0.136 (16)* | |
H12' | 0.57040 | 0.62420 | 0.09220 | 0.055 (6)* | |
H13 | 0.34880 | 0.54040 | 0.00990 | 0.072 (8)* | |
H14 | 0.12860 | 0.53400 | 0.05400 | 0.059 (7)* | |
H16 | 0.02310 | 0.65770 | 0.29700 | 0.048 (6)* | |
H17 | 0.25310 | 0.74490 | 0.37190 | 0.048 (6)* | |
H1 | 0.82400 | −0.01690 | 0.17800 | 0.080 (10)* | |
H2 | 0.85940 | 0.37080 | 0.21010 | 0.070 (8)* | |
H3 | 0.92330 | 0.48850 | 0.33260 | 0.050 (6)* | |
H4 | 0.96410 | 0.43190 | 0.42670 | 0.045 (6)* | |
H6 | 0.93960 | 0.10050 | 0.42430 | 0.052 (6)* | |
H7 | 0.87420 | −0.00940 | 0.29820 | 0.040 (5)* | |
H1B | 0.27230 | 0.80700 | 0.08630 | 0.099 (11)* | |
H2B | 0.08470 | 0.82020 | 0.14670 | 0.071 (8)* | |
H3B | 0.13280 | 0.91240 | 0.27360 | 0.071 (8)* | |
H5B | 0.56720 | 0.96170 | 0.26780 | 0.080 (9)* | |
H6B | 0.50780 | 0.87180 | 0.14040 | 0.071 (8)* | |
H8B | 0.19440 | 0.95230 | 0.39310 | 0.078 (8)* | |
H9B | 0.25610 | 1.05250 | 0.51910 | 0.072 (8)* | |
H11B | 0.65340 | 1.18700 | 0.49910 | 0.071 (8)* | |
H12B | 0.60390 | 1.09200 | 0.37290 | 0.065 (7)* | |
H2C | 0.07840 | 0.28870 | 0.02800 | 0.074 (8)* | |
H3C | 0.13410 | 0.38040 | 0.15480 | 0.070 (8)* | |
H5C | 0.55580 | 0.38170 | 0.14570 | 0.068 (8)* | |
H6C | 0.48330 | 0.28370 | 0.02020 | 0.070 (8)* | |
H8C | 0.19130 | 0.40600 | 0.27340 | 0.080 (9)* | |
H9C | 0.25530 | 0.50240 | 0.39930 | 0.076 (8)* | |
H10C | 0.48960 | 0.59690 | 0.44720 | 0.097 (11)* | |
H11C | 0.66820 | 0.61130 | 0.37980 | 0.062 (7)* | |
H12C | 0.61010 | 0.52170 | 0.25230 | 0.053 (6)* | |
H2A | 0.07970 | 0.06030 | 0.07560 | 0.103 (11)* | |
H3A | 0.13520 | 0.15390 | 0.20150 | 0.103 (11)* | |
H5A | 0.55560 | 0.15280 | 0.19340 | 0.091 (10)* | |
H6A | 0.48490 | 0.06080 | 0.06770 | 0.094 (10)* | |
H8A | 0.19410 | 0.16730 | 0.32230 | 0.072 (8)* | |
H9A | 0.26170 | 0.26130 | 0.44770 | 0.055 (6)* | |
H11A | 0.65990 | 0.39230 | 0.42700 | 0.071 (8)* | |
H12A | 0.60580 | 0.30140 | 0.30040 | 0.053 (6)* | |
H11 | 0.11830 | 0.15120 | 0.65030 | 0.128 (15)* | |
H12 | 0.05290 | 0.14840 | 0.58640 | 0.118 (15)* | |
H21 | 0.74520 | 0.11210 | 0.08870 | 0.14 (2)* | |
H22 | 0.82000 | 0.07400 | 0.04810 | 0.105 (13)* | |
H31 | 0.77450 | 0.22240 | 0.03750 | 0.067 (9)* | |
H32 | 0.79870 | 0.31370 | 0.03490 | 0.128 (15)* | |
H41 | 0.78270 | 0.80780 | 0.09660 | 0.115 (13)* | |
H42 | 0.80860 | 0.81520 | 0.16760 | 0.108 (13)* | |
H51 | 0.67750 | 0.74120 | 0.23740 | 0.134 (14)* | |
H52 | 0.79810 | 0.70560 | 0.22650 | 0.123 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0457 (3) | 0.0487 (3) | 0.0407 (3) | 0.0064 (2) | 0.0023 (2) | 0.0138 (2) |
O11 | 0.0525 (9) | 0.0732 (11) | 0.0329 (8) | 0.0125 (8) | −0.0008 (6) | 0.0079 (7) |
O12 | 0.0464 (9) | 0.0888 (13) | 0.0598 (10) | 0.0061 (8) | 0.0132 (8) | 0.0235 (10) |
O13 | 0.0669 (10) | 0.0766 (12) | 0.0588 (10) | 0.0160 (9) | −0.0065 (8) | 0.0351 (9) |
O14 | 0.0624 (10) | 0.0485 (9) | 0.0661 (11) | 0.0041 (8) | −0.0042 (8) | 0.0050 (8) |
N11 | 0.0491 (10) | 0.0514 (10) | 0.0362 (8) | 0.0130 (8) | 0.0085 (7) | 0.0130 (8) |
C12 | 0.0543 (13) | 0.0622 (14) | 0.0405 (11) | 0.0184 (11) | 0.0161 (10) | 0.0159 (10) |
C13 | 0.0644 (14) | 0.0574 (13) | 0.0300 (9) | 0.0160 (11) | 0.0117 (9) | 0.0140 (9) |
C14 | 0.0542 (12) | 0.0466 (11) | 0.0294 (9) | 0.0082 (9) | 0.0029 (9) | 0.0138 (8) |
C15 | 0.0442 (10) | 0.0382 (10) | 0.0317 (9) | 0.0062 (8) | 0.0041 (8) | 0.0139 (8) |
C16 | 0.0505 (11) | 0.0492 (11) | 0.0333 (9) | 0.0117 (9) | 0.0123 (9) | 0.0163 (9) |
C17 | 0.0596 (13) | 0.0515 (12) | 0.0275 (9) | 0.0141 (10) | 0.0076 (9) | 0.0122 (9) |
C18 | 0.0511 (12) | 0.0463 (11) | 0.0296 (9) | 0.0117 (9) | 0.0015 (8) | 0.0116 (8) |
C19 | 0.0462 (11) | 0.0409 (10) | 0.0310 (9) | 0.0119 (8) | 0.0063 (8) | 0.0144 (8) |
C20 | 0.0488 (11) | 0.0383 (10) | 0.0284 (8) | 0.0106 (8) | 0.0056 (8) | 0.0144 (8) |
S2 | 0.0902 (5) | 0.0671 (4) | 0.0268 (2) | 0.0378 (3) | 0.0012 (3) | 0.0088 (2) |
O1 | 0.0917 (12) | 0.0462 (9) | 0.0324 (7) | 0.0162 (8) | −0.0008 (8) | 0.0043 (6) |
O2 | 0.0745 (11) | 0.0647 (10) | 0.0433 (8) | 0.0223 (9) | 0.0252 (8) | 0.0092 (8) |
O3 | 0.0579 (11) | 0.1089 (16) | 0.0611 (11) | 0.0289 (11) | −0.0159 (9) | −0.0242 (11) |
O4 | 0.312 (4) | 0.1128 (18) | 0.0348 (9) | 0.126 (2) | 0.0058 (16) | 0.0259 (11) |
N1 | 0.0522 (10) | 0.0525 (11) | 0.0330 (8) | 0.0124 (8) | 0.0061 (7) | 0.0176 (8) |
C2 | 0.0554 (13) | 0.0560 (13) | 0.0417 (11) | 0.0121 (10) | 0.0104 (10) | 0.0247 (10) |
C3 | 0.0568 (13) | 0.0431 (12) | 0.0476 (12) | 0.0085 (9) | 0.0123 (10) | 0.0185 (10) |
C4 | 0.0456 (11) | 0.0429 (11) | 0.0345 (10) | 0.0074 (9) | 0.0099 (8) | 0.0103 (8) |
C5 | 0.0437 (10) | 0.0499 (12) | 0.0297 (9) | 0.0134 (9) | 0.0040 (8) | 0.0120 (8) |
C6 | 0.0536 (12) | 0.0522 (12) | 0.0367 (10) | 0.0163 (10) | 0.0059 (9) | 0.0189 (9) |
C7 | 0.0507 (12) | 0.0403 (11) | 0.0409 (11) | 0.0102 (9) | 0.0063 (9) | 0.0111 (9) |
C8 | 0.0453 (11) | 0.0448 (11) | 0.0309 (9) | 0.0076 (9) | 0.0050 (8) | 0.0083 (8) |
C9 | 0.0364 (9) | 0.0450 (11) | 0.0293 (8) | 0.0065 (8) | 0.0045 (7) | 0.0122 (8) |
C10 | 0.0334 (9) | 0.0420 (10) | 0.0318 (9) | 0.0059 (8) | 0.0052 (7) | 0.0112 (8) |
N1B | 0.0820 (15) | 0.0482 (11) | 0.0407 (10) | 0.0110 (10) | −0.0042 (10) | 0.0122 (9) |
N10B | 0.0658 (12) | 0.0696 (13) | 0.0365 (9) | 0.0125 (10) | 0.0029 (9) | 0.0135 (9) |
C2B | 0.0655 (16) | 0.0625 (15) | 0.0497 (13) | 0.0115 (12) | −0.0139 (12) | 0.0099 (12) |
C3B | 0.0541 (13) | 0.0619 (15) | 0.0494 (13) | 0.0120 (11) | −0.0009 (11) | 0.0132 (11) |
C4B | 0.0524 (12) | 0.0420 (11) | 0.0391 (10) | 0.0064 (9) | −0.0002 (9) | 0.0151 (9) |
C5B | 0.0527 (13) | 0.0591 (14) | 0.0430 (12) | 0.0039 (10) | 0.0017 (10) | 0.0141 (10) |
C6B | 0.0736 (16) | 0.0565 (14) | 0.0433 (12) | 0.0087 (12) | 0.0106 (12) | 0.0144 (11) |
C7B | 0.0486 (11) | 0.0492 (12) | 0.0388 (10) | 0.0086 (9) | 0.0010 (9) | 0.0162 (9) |
C8B | 0.0558 (14) | 0.0630 (15) | 0.0429 (11) | −0.0003 (11) | 0.0046 (10) | 0.0159 (11) |
C9B | 0.0631 (15) | 0.0747 (17) | 0.0452 (12) | 0.0099 (13) | 0.0136 (11) | 0.0204 (12) |
C11B | 0.0561 (14) | 0.0697 (16) | 0.0423 (12) | 0.0022 (12) | −0.0045 (11) | 0.0095 (11) |
C12B | 0.0483 (12) | 0.0688 (15) | 0.0387 (11) | 0.0072 (11) | 0.0034 (10) | 0.0121 (11) |
N1C | 0.0845 (15) | 0.0568 (12) | 0.0421 (10) | 0.0202 (11) | 0.0071 (11) | 0.0138 (9) |
N10C | 0.0616 (12) | 0.0696 (13) | 0.0377 (10) | 0.0184 (10) | 0.0049 (9) | 0.0141 (9) |
C2C | 0.0655 (15) | 0.0658 (16) | 0.0476 (13) | 0.0161 (12) | −0.0028 (12) | 0.0138 (12) |
C3C | 0.0549 (13) | 0.0603 (14) | 0.0472 (12) | 0.0179 (11) | 0.0066 (10) | 0.0171 (11) |
C4C | 0.0527 (12) | 0.0428 (11) | 0.0385 (10) | 0.0131 (9) | 0.0085 (9) | 0.0180 (9) |
C5C | 0.0537 (13) | 0.0680 (15) | 0.0442 (12) | 0.0185 (11) | 0.0106 (10) | 0.0196 (11) |
C6C | 0.0778 (17) | 0.0694 (16) | 0.0449 (12) | 0.0279 (14) | 0.0201 (13) | 0.0188 (12) |
C7C | 0.0475 (11) | 0.0470 (11) | 0.0400 (10) | 0.0161 (9) | 0.0079 (9) | 0.0194 (9) |
C8C | 0.0452 (12) | 0.0741 (16) | 0.0443 (12) | 0.0125 (11) | 0.0089 (10) | 0.0114 (11) |
C9C | 0.0533 (14) | 0.0862 (19) | 0.0470 (13) | 0.0180 (13) | 0.0148 (11) | 0.0155 (13) |
C11C | 0.0515 (13) | 0.0678 (15) | 0.0468 (12) | 0.0075 (11) | 0.0030 (10) | 0.0213 (11) |
C12C | 0.0503 (12) | 0.0647 (14) | 0.0434 (11) | 0.0092 (10) | 0.0102 (10) | 0.0250 (11) |
N1A | 0.124 (2) | 0.0760 (17) | 0.0513 (13) | 0.0254 (16) | 0.0017 (15) | 0.0188 (12) |
N10A | 0.0553 (11) | 0.0761 (14) | 0.0452 (10) | 0.0197 (10) | 0.0112 (9) | 0.0173 (10) |
C2A | 0.091 (2) | 0.100 (2) | 0.0603 (18) | 0.0239 (19) | −0.0157 (17) | 0.0202 (17) |
C3A | 0.0708 (17) | 0.087 (2) | 0.0579 (15) | 0.0222 (15) | 0.0017 (14) | 0.0221 (15) |
C4A | 0.0573 (13) | 0.0492 (12) | 0.0444 (11) | 0.0118 (10) | 0.0052 (10) | 0.0211 (10) |
C5A | 0.0708 (17) | 0.0709 (17) | 0.0528 (14) | 0.0175 (13) | 0.0135 (13) | 0.0174 (13) |
C6A | 0.113 (3) | 0.082 (2) | 0.0510 (15) | 0.0334 (19) | 0.0226 (17) | 0.0157 (14) |
C7A | 0.0482 (11) | 0.0515 (12) | 0.0446 (11) | 0.0143 (9) | 0.0080 (9) | 0.0207 (10) |
C8A | 0.0457 (12) | 0.0684 (15) | 0.0544 (13) | 0.0088 (11) | 0.0108 (10) | 0.0210 (12) |
C9A | 0.0493 (13) | 0.0856 (18) | 0.0524 (13) | 0.0174 (12) | 0.0181 (11) | 0.0225 (13) |
C11A | 0.0491 (13) | 0.0781 (17) | 0.0505 (13) | 0.0099 (12) | 0.0072 (11) | 0.0174 (12) |
C12A | 0.0496 (13) | 0.0727 (16) | 0.0522 (13) | 0.0120 (11) | 0.0144 (11) | 0.0251 (12) |
O1W | 0.0901 (14) | 0.0730 (13) | 0.0819 (15) | 0.0155 (11) | −0.0042 (12) | 0.0363 (12) |
O2W | 0.306 (5) | 0.102 (2) | 0.0443 (12) | 0.070 (3) | 0.007 (2) | 0.0203 (14) |
O3W | 0.1048 (15) | 0.0585 (11) | 0.0523 (10) | 0.0120 (11) | −0.0120 (10) | 0.0054 (9) |
O4W | 0.158 (2) | 0.0514 (10) | 0.0476 (10) | 0.0223 (12) | 0.0087 (12) | 0.0071 (9) |
O5W | 0.0570 (10) | 0.0710 (12) | 0.0697 (11) | 0.0176 (9) | 0.0058 (9) | 0.0191 (10) |
Geometric parameters (Å, º) top
S1—O12 | 1.4413 (19) | C7—C8 | 1.364 (3) |
S1—O13 | 1.444 (2) | C8—C9 | 1.419 (3) |
S1—O14 | 1.442 (2) | C9—C10 | 1.420 (3) |
S1—C15 | 1.770 (2) | C2—H2 | 0.9306 |
S2—O2 | 1.432 (2) | C3—H3 | 0.9300 |
S2—O3 | 1.451 (2) | C4—H4 | 0.9302 |
S2—O4 | 1.437 (3) | C6—H6 | 0.9290 |
S2—C5 | 1.777 (2) | C7—H7 | 0.9295 |
O11—C18 | 1.346 (3) | C2B—C3B | 1.367 (4) |
O11—H11' | 0.8185 | C3B—C4B | 1.389 (4) |
O1—C8 | 1.346 (2) | C4B—C7B | 1.474 (3) |
O1—H1 | 0.8193 | C4B—C5B | 1.386 (3) |
N11—C12 | 1.319 (3) | C5B—C6B | 1.372 (3) |
N11—C19 | 1.366 (3) | C7B—C12B | 1.391 (4) |
O1W—H12 | 0.8370 | C7B—C8B | 1.371 (3) |
O1W—H11 | 0.8794 | C8B—C9B | 1.384 (3) |
N1—C2 | 1.319 (3) | C11B—C12B | 1.377 (3) |
N1—C9 | 1.368 (3) | C2B—H2B | 0.9303 |
O2W—H22 | 0.8137 | C3B—H3B | 0.9301 |
O2W—H21 | 0.8197 | C5B—H5B | 0.9305 |
N1B—C6B | 1.323 (4) | C6B—H6B | 0.9297 |
N1B—C2B | 1.317 (4) | C8B—H8B | 0.9301 |
N10B—C9B | 1.334 (4) | C9B—H9B | 0.9303 |
N10B—C11B | 1.321 (3) | C11B—H11B | 0.9298 |
N1B—H1B | 0.8596 | C12B—H12B | 0.9295 |
O3W—H31 | 0.8751 | C2C—C3C | 1.378 (3) |
O3W—H32 | 0.8571 | C3C—C4C | 1.380 (3) |
N1C—C2C | 1.322 (4) | C4C—C5C | 1.382 (3) |
N1C—C6C | 1.323 (4) | C4C—C7C | 1.484 (3) |
N10C—C9C | 1.329 (4) | C5C—C6C | 1.378 (3) |
N10C—C11C | 1.328 (3) | C7C—C12C | 1.391 (4) |
O4W—H42 | 0.8434 | C7C—C8C | 1.375 (3) |
O4W—H41 | 0.8333 | C8C—C9C | 1.363 (3) |
N10C—H10C | 0.8615 | C11C—C12C | 1.369 (3) |
N1A—C6A | 1.315 (5) | C2C—H2C | 0.9295 |
N1A—C2A | 1.315 (5) | C3C—H3C | 0.9301 |
N10A—C11A | 1.318 (4) | C5C—H5C | 0.9298 |
N10A—C9A | 1.332 (4) | C6C—H6C | 0.9299 |
O5W—H51 | 0.9923 | C8C—H8C | 0.9300 |
O5W—H52 | 0.8572 | C9C—H9C | 0.9294 |
C12—C13 | 1.391 (4) | C11C—H11C | 0.9303 |
C13—C14 | 1.357 (3) | C12C—H12C | 0.9290 |
C14—C20 | 1.413 (3) | C2A—C3A | 1.373 (4) |
C15—C16 | 1.369 (3) | C3A—C4A | 1.378 (4) |
C15—C20 | 1.425 (3) | C4A—C7A | 1.478 (3) |
C16—C17 | 1.392 (3) | C4A—C5A | 1.377 (4) |
C17—C18 | 1.365 (3) | C5A—C6A | 1.372 (4) |
C18—C19 | 1.426 (3) | C7A—C8A | 1.381 (4) |
C19—C20 | 1.408 (3) | C7A—C12A | 1.392 (4) |
C12—H12' | 0.9299 | C8A—C9A | 1.364 (4) |
C13—H13 | 0.9296 | C11A—C12A | 1.371 (4) |
C14—H14 | 0.9299 | C2A—H2A | 0.9300 |
C16—H16 | 0.9305 | C3A—H3A | 0.9294 |
C17—H17 | 0.9302 | C5A—H5A | 0.9307 |
C2—C3 | 1.390 (3) | C6A—H6A | 0.9302 |
C3—C4 | 1.366 (3) | C8A—H8A | 0.9305 |
C4—C10 | 1.409 (3) | C9A—H9A | 0.9302 |
C5—C6 | 1.366 (3) | C11A—H11A | 0.9302 |
C5—C10 | 1.426 (3) | C12A—H12A | 0.9315 |
C6—C7 | 1.409 (3) | | |
| | | |
S1···H14 | 2.7747 | C3A···H8A | 2.7413 |
S1···H32i | 3.1474 | C3B···H8B | 2.6877 |
S1···H52i | 2.7383 | C3C···H8C | 2.6843 |
S2···H9Aii | 3.0746 | C4···H11A | 2.8692 |
S2···H11Biii | 3.1737 | C4···H9Cii | 2.9641 |
S2···H4 | 2.7693 | C5···H9Aii | 2.9386 |
O1···N1 | 2.641 (3) | C5A···H12A | 2.7390 |
O1···O2W | 2.991 (3) | C5B···H12B | 2.6509 |
O1···O4Wiii | 2.574 (3) | C5C···H12C | 2.7021 |
O1W···O4i | 2.796 (4) | C6···H8Aii | 2.9501 |
O2···C9Civ | 3.293 (3) | C6···H12Biii | 2.9180 |
O2···C4 | 3.155 (3) | C6A···H21 | 3.0750 |
O2···C4v | 3.388 (3) | C7···H12Biii | 3.0376 |
O2W···N1 | 2.843 (3) | C7···H5Biii | 2.8963 |
O2W···O1 | 2.991 (3) | C7···H8Aii | 2.8879 |
O2W···O3W | 2.580 (4) | C8···H3Aii | 2.9269 |
O3···C11Cv | 3.370 (4) | C8···H8Aii | 3.0635 |
O3···C4v | 3.348 (3) | C8···H5Biii | 3.0309 |
O3···C9Aii | 3.236 (4) | C8A···H3A | 2.7396 |
O3···C4 | 3.175 (3) | C8B···H3B | 2.6840 |
O3W···O14ii | 2.679 (3) | C8C···H3C | 2.6943 |
O3W···O2W | 2.580 (4) | C9···H3Aii | 3.0767 |
O4···O1Wii | 2.796 (4) | C9A···H10Civ | 2.7602 |
O4W···C8vi | 3.413 (3) | C9B···H11'vii | 2.7740 |
O4W···O1vi | 2.574 (3) | C11A···H10Civ | 2.8052 |
O4W···O5W | 2.736 (3) | C11B···H17vii | 2.9640 |
O5W···C12 | 3.408 (3) | C11B···H11'vii | 2.8626 |
O5W···O4W | 2.736 (3) | C12···H51 | 2.6705 |
O5W···O11 | 3.153 (3) | C12A···H5A | 2.7422 |
O5W···O12ii | 2.848 (3) | C12B···H5B | 2.6560 |
O5W···N11 | 2.761 (3) | C12C···H5C | 2.6997 |
O11···O5W | 3.153 (3) | C18···H51 | 3.0924 |
O11···C5B | 3.419 (3) | C19···H51 | 2.8493 |
O11···N10Bvii | 2.690 (2) | H1···H7 | 2.3132 |
O11···C11C | 3.283 (4) | H1···H42iii | 2.3062 |
O11···N11 | 2.643 (2) | H1···H41iii | 2.3512 |
O12···O5Wi | 2.848 (3) | H1···O4Wiii | 1.7664 |
O12···C12Ci | 3.210 (3) | H1B···O3Wix | 1.7306 |
O13···C14 | 3.247 (3) | H1B···H32ix | 2.2952 |
O14···O3Wi | 2.679 (3) | H1B···H31ix | 2.2819 |
O14···C14 | 3.110 (3) | H2···O14ii | 2.7012 |
O1···H21 | 2.5790 | H2B···O4Wi | 2.6535 |
O1···H22 | 2.8828 | H2B···O13 | 2.8573 |
O1W···H9Biii | 2.5526 | H3···O3v | 2.9037 |
O2···H9Civ | 2.5959 | H3A···C8A | 2.7396 |
O2···H11Biii | 2.6271 | H3A···C9i | 3.0767 |
O2···H4v | 2.7741 | H3A···C8i | 2.9269 |
O2···H4 | 2.6311 | H3A···H8A | 2.3059 |
O2W···H31 | 1.7283 | H3B···C8B | 2.6840 |
O3···H3v | 2.9037 | H3B···H8B | 2.1831 |
O3···H4 | 2.6286 | H3C···O14 | 2.8188 |
O3···H9Aii | 2.5717 | H3C···H8C | 2.2080 |
O3···H4v | 2.7514 | H3C···C8C | 2.6943 |
O3···H11Cv | 2.6588 | H4···O3 | 2.6286 |
O3W···H6C | 2.6042 | H4···S2 | 2.7693 |
O4···H16iv | 2.8924 | H4···O3v | 2.7514 |
O4···H17iv | 2.9156 | H4···O2v | 2.7741 |
O4···H6 | 2.4334 | H4···O2 | 2.6311 |
O4···H12ii | 1.9607 | H5A···N1 | 2.7525 |
O4W···H1vi | 1.7664 | H5A···H12A | 2.2933 |
O5W···H42 | 1.9087 | H5A···C12A | 2.7422 |
O5W···H7vi | 2.8646 | H5B···C7vi | 2.8963 |
O11···H51 | 2.4505 | H5B···C12B | 2.6560 |
O12···H16 | 2.4337 | H5B···H12B | 2.1487 |
O12···H52i | 2.0017 | H5B···C8vi | 3.0309 |
O12···H12Ci | 2.2894 | H5C···C12C | 2.6997 |
O12···H5Ci | 2.8291 | H5C···O12ii | 2.8291 |
O13···H14viii | 2.8709 | H5C···H12C | 2.2206 |
O13···H52i | 2.7492 | H6···O1Wxi | 2.7991 |
O13···H13viii | 2.8199 | H6···O4 | 2.4334 |
O13···H14 | 2.7305 | H6A···H21 | 2.3427 |
O13···H2B | 2.8573 | H6C···O3W | 2.6042 |
O14···H31i | 2.8598 | H7···O1Wxi | 2.8189 |
O14···H2i | 2.7012 | H7···H11xi | 2.5818 |
O14···H32i | 1.8289 | H7···O5Wiii | 2.8646 |
O14···H3C | 2.8188 | H7···H1 | 2.3132 |
O14···H14 | 2.5686 | H8A···C7i | 2.8879 |
N1···O2W | 2.843 (3) | H8A···H3A | 2.3059 |
N1···O1 | 2.641 (3) | H8A···C6i | 2.9501 |
N1B···C20 | 3.391 (3) | H8A···C3A | 2.7413 |
N1B···O3Wix | 2.584 (3) | H8A···C8i | 3.0635 |
N10A···C11Biii | 3.369 (4) | H8B···H12x | 2.5529 |
N10A···N10Civ | 2.717 (3) | H8B···O1Wx | 2.4620 |
N10B···O11vii | 2.690 (2) | H8B···C3B | 2.6877 |
N11···C6B | 3.296 (4) | H8B···H3B | 2.1831 |
N11···O5W | 2.761 (3) | H8C···C2i | 2.8494 |
N11···O11 | 2.643 (2) | H8C···H3C | 2.2080 |
N1···H21 | 2.6342 | H8C···C3C | 2.6843 |
N1···H5A | 2.7525 | H8C···C3i | 2.8663 |
N10A···H10Civ | 1.8564 | H9A···O3i | 2.5717 |
N10B···H11'vii | 1.8904 | H9A···S2i | 3.0746 |
N11···H52 | 2.8307 | H9A···C5i | 2.9386 |
N11···H51 | 1.8175 | H9B···O1Wvi | 2.5526 |
C2B···C20 | 3.429 (4) | H9C···O2iv | 2.5959 |
C2B···C15 | 3.527 (4) | H9C···C4i | 2.9641 |
C2C···C14 | 3.469 (4) | H11'···H17 | 2.3255 |
C3···C8Cii | 3.559 (4) | H11'···N10Bvii | 1.8904 |
C3B···C17 | 3.589 (4) | H11'···C11Bvii | 2.8626 |
C3C···C14 | 3.302 (4) | H11'···C9Bvii | 2.7740 |
C3C···C20 | 3.407 (4) | H11A···C4 | 2.8692 |
C4···O3 | 3.175 (3) | H11B···S2vi | 3.1737 |
C4···O3v | 3.348 (3) | H11B···O2vi | 2.6271 |
C4···C11A | 3.532 (4) | H11B···H17vii | 2.3534 |
C4···O2v | 3.388 (3) | H11C···O3v | 2.6588 |
C4···O2 | 3.155 (3) | H12···O4i | 1.9607 |
C4B···C17 | 3.594 (4) | H12A···C2 | 2.8146 |
C4B···C18 | 3.381 (3) | H12A···C5A | 2.7390 |
C5···C9Aii | 3.571 (4) | H12A···C3 | 2.8807 |
C5A···C6Biii | 3.575 (4) | H12A···H5A | 2.2933 |
C5B···O11 | 3.419 (3) | H12B···C7vi | 3.0376 |
C5B···C18 | 3.444 (4) | H12B···H5B | 2.1487 |
C5B···C19 | 3.506 (4) | H12B···C5B | 2.6509 |
C6B···C19 | 3.367 (4) | H12B···C6vi | 2.9180 |
C6B···O3Wix | 3.351 (3) | H12C···C5C | 2.7021 |
C6B···C5Avi | 3.575 (4) | H12C···H5C | 2.2206 |
C6B···N11 | 3.296 (4) | H12C···O12ii | 2.2894 |
C7B···C8Avi | 3.472 (4) | H13···O13viii | 2.8199 |
C7C···C19 | 3.478 (3) | H14···O13viii | 2.8709 |
C8···O4Wiii | 3.413 (3) | H14···O13 | 2.7305 |
C8A···C7Biii | 3.472 (4) | H14···O14 | 2.5686 |
C8B···O1Wx | 3.312 (4) | H14···S1 | 2.7747 |
C8C···C3i | 3.559 (4) | H16···O4iv | 2.8924 |
C9A···C11Biii | 3.580 (4) | H16···O12 | 2.4337 |
C9A···C5i | 3.571 (4) | H17···H11' | 2.3255 |
C9A···C12Biii | 3.592 (4) | H17···O4iv | 2.9156 |
C9A···O3i | 3.236 (4) | H17···H11Bvii | 2.3534 |
C9B···C11Bvii | 3.539 (4) | H17···C11Bvii | 2.9640 |
C9C···O2iv | 3.293 (3) | H21···O1 | 2.5790 |
C11A···C4 | 3.532 (4) | H21···C6A | 3.0750 |
C11B···C9Bvii | 3.539 (4) | H21···H31 | 2.1240 |
C11B···C9Avi | 3.580 (4) | H21···H6A | 2.3427 |
C11B···N10Avi | 3.369 (4) | H21···N1 | 2.6342 |
C11C···O3v | 3.370 (4) | H22···H31 | 2.3494 |
C11C···O11 | 3.283 (4) | H22···O1 | 2.8828 |
C12···O5W | 3.408 (3) | H22···H2Aii | 2.5489 |
C12B···C9Avi | 3.592 (4) | H31···H21 | 2.1240 |
C12C···C18 | 3.582 (4) | H31···O2W | 1.7283 |
C12C···O12ii | 3.210 (3) | H31···O14ii | 2.8598 |
C14···C3C | 3.302 (4) | H31···H22 | 2.3494 |
C14···C2C | 3.469 (4) | H32···S1ii | 3.1474 |
C14···O13 | 3.247 (3) | H32···O14ii | 1.8289 |
C14···O14 | 3.110 (3) | H41···H1vi | 2.3512 |
C15···C2B | 3.527 (4) | H42···O5W | 1.9087 |
C17···C3B | 3.589 (4) | H42···H1vi | 2.3062 |
C17···C4B | 3.594 (4) | H42···H51 | 2.2553 |
C18···C4B | 3.381 (3) | H42···H52 | 2.2402 |
C18···C12C | 3.582 (4) | H51···O11 | 2.4505 |
C18···C5B | 3.444 (4) | H51···N11 | 1.8175 |
C19···C6B | 3.367 (4) | H51···C12 | 2.6705 |
C19···C5B | 3.506 (4) | H51···C18 | 3.0924 |
C19···C7C | 3.478 (3) | H51···C19 | 2.8493 |
C20···C2B | 3.429 (4) | H51···H42 | 2.2553 |
C20···C3C | 3.407 (4) | H52···S1ii | 2.7383 |
C20···N1B | 3.391 (3) | H52···O12ii | 2.0017 |
C2···H8Cii | 2.8494 | H52···O13ii | 2.7492 |
C2···H12A | 2.8146 | H52···N11 | 2.8307 |
C3···H12A | 2.8807 | H52···H42 | 2.2402 |
C3···H8Cii | 2.8663 | | |
| | | |
O12—S1—O13 | 112.76 (12) | C3B—C4B—C7B | 122.0 (2) |
O12—S1—O14 | 112.21 (12) | C5B—C4B—C7B | 120.95 (19) |
O12—S1—C15 | 105.43 (10) | C4B—C5B—C6B | 119.8 (3) |
O13—S1—O14 | 113.37 (11) | N1B—C6B—C5B | 121.0 (3) |
O13—S1—C15 | 106.71 (11) | C8B—C7B—C12B | 117.1 (2) |
O14—S1—C15 | 105.59 (10) | C4B—C7B—C12B | 120.95 (19) |
O2—S2—C5 | 106.05 (10) | C4B—C7B—C8B | 121.9 (2) |
O3—S2—O4 | 114.46 (17) | C7B—C8B—C9B | 119.3 (3) |
O3—S2—C5 | 106.19 (11) | N10B—C9B—C8B | 123.5 (2) |
O4—S2—C5 | 105.02 (12) | N10B—C11B—C12B | 123.2 (3) |
O2—S2—O3 | 112.16 (13) | C7B—C12B—C11B | 119.8 (2) |
O2—S2—O4 | 112.14 (17) | C3B—C2B—H2B | 119.77 |
C18—O11—H11' | 109.55 | N1B—C2B—H2B | 119.69 |
C8—O1—H1 | 109.48 | C2B—C3B—H3B | 119.74 |
C12—N11—C19 | 117.7 (2) | C4B—C3B—H3B | 119.79 |
H11—O1W—H12 | 101.99 | C4B—C5B—H5B | 120.15 |
C2—N1—C9 | 117.86 (17) | C6B—C5B—H5B | 120.06 |
H21—O2W—H22 | 91.99 | N1B—C6B—H6B | 119.55 |
C2B—N1B—C6B | 121.2 (2) | C5B—C6B—H6B | 119.48 |
C9B—N10B—C11B | 117.1 (2) | C7B—C8B—H8B | 120.33 |
C6B—N1B—H1B | 119.42 | C9B—C8B—H8B | 120.35 |
C2B—N1B—H1B | 119.36 | N10B—C9B—H9B | 118.27 |
H31—O3W—H32 | 96.23 | C8B—C9B—H9B | 118.25 |
C2C—N1C—C6C | 116.6 (2) | C12B—C11B—H11B | 118.34 |
C9C—N10C—C11C | 121.2 (2) | N10B—C11B—H11B | 118.48 |
H41—O4W—H42 | 106.94 | C11B—C12B—H12B | 120.12 |
C11C—N10C—H10C | 119.46 | C7B—C12B—H12B | 120.11 |
C9C—N10C—H10C | 119.31 | N1C—C2C—C3C | 123.2 (3) |
C2A—N1A—C6A | 116.1 (3) | C2C—C3C—C4C | 119.9 (2) |
C9A—N10A—C11A | 117.6 (2) | C5C—C4C—C7C | 121.06 (19) |
H51—O5W—H52 | 94.53 | C3C—C4C—C7C | 121.81 (19) |
N11—C12—C13 | 123.7 (2) | C3C—C4C—C5C | 117.1 (2) |
C12—C13—C14 | 119.4 (2) | C4C—C5C—C6C | 118.5 (2) |
C13—C14—C20 | 119.42 (19) | N1C—C6C—C5C | 124.6 (3) |
C16—C15—C20 | 119.28 (18) | C8C—C7C—C12C | 117.4 (2) |
S1—C15—C20 | 120.77 (14) | C4C—C7C—C8C | 121.0 (2) |
S1—C15—C16 | 119.93 (15) | C4C—C7C—C12C | 121.64 (19) |
C15—C16—C17 | 122.01 (19) | C7C—C8C—C9C | 120.5 (3) |
C16—C17—C18 | 120.75 (18) | N10C—C9C—C8C | 120.5 (3) |
O11—C18—C17 | 124.69 (18) | N10C—C11C—C12C | 120.2 (3) |
O11—C18—C19 | 116.60 (17) | C7C—C12C—C11C | 120.2 (2) |
C17—C18—C19 | 118.71 (18) | N1C—C2C—H2C | 118.38 |
N11—C19—C18 | 116.67 (17) | C3C—C2C—H2C | 118.46 |
C18—C19—C20 | 120.88 (18) | C2C—C3C—H3C | 120.07 |
N11—C19—C20 | 122.46 (17) | C4C—C3C—H3C | 119.99 |
C14—C20—C19 | 117.29 (18) | C6C—C5C—H5C | 120.76 |
C14—C20—C15 | 124.38 (18) | C4C—C5C—H5C | 120.72 |
C15—C20—C19 | 118.32 (16) | N1C—C6C—H6C | 117.67 |
N11—C12—H12' | 118.08 | C5C—C6C—H6C | 117.72 |
C13—C12—H12' | 118.22 | C7C—C8C—H8C | 119.84 |
C12—C13—H13 | 120.28 | C9C—C8C—H8C | 119.65 |
C14—C13—H13 | 120.30 | C8C—C9C—H9C | 119.72 |
C20—C14—H14 | 120.31 | N10C—C9C—H9C | 119.75 |
C13—C14—H14 | 120.27 | C12C—C11C—H11C | 119.90 |
C17—C16—H16 | 118.96 | N10C—C11C—H11C | 119.92 |
C15—C16—H16 | 119.03 | C11C—C12C—H12C | 119.90 |
C18—C17—H17 | 119.62 | C7C—C12C—H12C | 119.93 |
C16—C17—H17 | 119.63 | N1A—C2A—C3A | 123.5 (3) |
N1—C2—C3 | 123.6 (2) | C2A—C3A—C4A | 120.0 (3) |
C2—C3—C4 | 119.4 (2) | C5A—C4A—C7A | 121.4 (2) |
C3—C4—C10 | 119.76 (19) | C3A—C4A—C7A | 121.7 (2) |
S2—C5—C10 | 120.49 (17) | C3A—C4A—C5A | 116.9 (2) |
C6—C5—C10 | 119.33 (18) | C4A—C5A—C6A | 118.4 (3) |
S2—C5—C6 | 120.18 (16) | N1A—C6A—C5A | 125.3 (3) |
C5—C6—C7 | 122.0 (2) | C4A—C7A—C8A | 121.5 (2) |
C6—C7—C8 | 120.0 (2) | C8A—C7A—C12A | 116.5 (2) |
O1—C8—C9 | 116.12 (19) | C4A—C7A—C12A | 122.0 (2) |
C7—C8—C9 | 119.93 (18) | C7A—C8A—C9A | 119.4 (3) |
O1—C8—C7 | 124.0 (2) | N10A—C9A—C8A | 123.7 (3) |
N1—C9—C10 | 122.6 (2) | N10A—C11A—C12A | 122.6 (3) |
C8—C9—C10 | 120.05 (18) | C7A—C12A—C11A | 120.2 (3) |
N1—C9—C8 | 117.38 (17) | N1A—C2A—H2A | 118.32 |
C4—C10—C9 | 116.77 (18) | C3A—C2A—H2A | 118.19 |
C4—C10—C5 | 124.53 (17) | C2A—C3A—H3A | 119.95 |
C5—C10—C9 | 118.69 (19) | C4A—C3A—H3A | 120.10 |
C3—C2—H2 | 118.16 | C6A—C5A—H5A | 120.88 |
N1—C2—H2 | 118.24 | C4A—C5A—H5A | 120.76 |
C4—C3—H3 | 120.22 | C5A—C6A—H6A | 117.28 |
C2—C3—H3 | 120.36 | N1A—C6A—H6A | 117.47 |
C3—C4—H4 | 120.07 | C7A—C8A—H8A | 120.31 |
C10—C4—H4 | 120.16 | C9A—C8A—H8A | 120.32 |
C7—C6—H6 | 119.05 | N10A—C9A—H9A | 118.12 |
C5—C6—H6 | 118.98 | C8A—C9A—H9A | 118.14 |
C6—C7—H7 | 119.99 | C12A—C11A—H11A | 118.73 |
C8—C7—H7 | 119.99 | N10A—C11A—H11A | 118.69 |
N1B—C2B—C3B | 120.5 (3) | C11A—C12A—H12A | 119.92 |
C2B—C3B—C4B | 120.5 (3) | C7A—C12A—H12A | 119.84 |
C3B—C4B—C5B | 117.0 (2) | | |
| | | |
O12—S1—C15—C16 | −4.5 (2) | C10—C5—C6—C7 | −0.5 (3) |
O12—S1—C15—C20 | 177.15 (19) | C5—C6—C7—C8 | −0.4 (3) |
O13—S1—C15—C16 | 115.6 (2) | C6—C7—C8—O1 | −178.5 (2) |
O13—S1—C15—C20 | −62.7 (2) | C6—C7—C8—C9 | 1.3 (3) |
O14—S1—C15—C16 | −123.5 (2) | C7—C8—C9—C10 | −1.2 (3) |
O14—S1—C15—C20 | 58.2 (2) | O1—C8—C9—N1 | −1.2 (3) |
O4—S2—C5—C6 | −1.3 (2) | O1—C8—C9—C10 | 178.56 (18) |
O4—S2—C5—C10 | 177.5 (2) | C7—C8—C9—N1 | 178.99 (19) |
O2—S2—C5—C10 | 58.62 (19) | N1—C9—C10—C5 | −179.91 (18) |
O3—S2—C5—C6 | 120.28 (19) | C8—C9—C10—C5 | 0.3 (3) |
O2—S2—C5—C6 | −120.23 (18) | C8—C9—C10—C4 | −179.59 (18) |
O3—S2—C5—C10 | −60.9 (2) | N1—C9—C10—C4 | 0.2 (3) |
C12—N11—C19—C20 | −0.7 (3) | N1B—C2B—C3B—C4B | −0.9 (4) |
C19—N11—C12—C13 | 1.7 (4) | C2B—C3B—C4B—C5B | −0.6 (4) |
C12—N11—C19—C18 | 179.4 (2) | C2B—C3B—C4B—C7B | 179.6 (3) |
C2—N1—C9—C8 | 179.42 (19) | C3B—C4B—C7B—C12B | −157.7 (3) |
C2—N1—C9—C10 | −0.4 (3) | C5B—C4B—C7B—C12B | 22.5 (4) |
C9—N1—C2—C3 | 0.1 (3) | C5B—C4B—C7B—C8B | −159.7 (3) |
C2B—N1B—C6B—C5B | −0.5 (4) | C3B—C4B—C5B—C6B | 1.6 (4) |
C6B—N1B—C2B—C3B | 1.5 (4) | C3B—C4B—C7B—C8B | 20.1 (4) |
C9B—N10B—C11B—C12B | −0.1 (4) | C7B—C4B—C5B—C6B | −178.6 (2) |
C11B—N10B—C9B—C8B | 0.3 (4) | C4B—C5B—C6B—N1B | −1.1 (4) |
C6C—N1C—C2C—C3C | −1.2 (4) | C12B—C7B—C8B—C9B | −0.3 (4) |
C2C—N1C—C6C—C5C | −0.3 (4) | C4B—C7B—C12B—C11B | 178.3 (2) |
C9C—N10C—C11C—C12C | −0.2 (4) | C4B—C7B—C8B—C9B | −178.1 (2) |
C11C—N10C—C9C—C8C | 1.6 (4) | C8B—C7B—C12B—C11B | 0.5 (4) |
C6A—N1A—C2A—C3A | −0.1 (6) | C7B—C8B—C9B—N10B | −0.1 (4) |
C2A—N1A—C6A—C5A | 0.5 (6) | N10B—C11B—C12B—C7B | −0.3 (4) |
C9A—N10A—C11A—C12A | 0.3 (4) | N1C—C2C—C3C—C4C | 1.4 (4) |
C11A—N10A—C9A—C8A | −0.5 (4) | C2C—C3C—C4C—C5C | 0.0 (4) |
N11—C12—C13—C14 | −1.2 (4) | C2C—C3C—C4C—C7C | 179.9 (2) |
C12—C13—C14—C20 | −0.3 (4) | C5C—C4C—C7C—C12C | 25.2 (4) |
C13—C14—C20—C15 | −177.4 (2) | C7C—C4C—C5C—C6C | 178.7 (2) |
C13—C14—C20—C19 | 1.2 (3) | C3C—C4C—C7C—C12C | −154.7 (3) |
C16—C15—C20—C19 | 0.3 (3) | C5C—C4C—C7C—C8C | −154.7 (3) |
S1—C15—C20—C14 | −2.8 (3) | C3C—C4C—C7C—C8C | 25.3 (4) |
S1—C15—C16—C17 | −177.46 (19) | C3C—C4C—C5C—C6C | −1.4 (4) |
C16—C15—C20—C14 | 178.9 (2) | C4C—C5C—C6C—N1C | 1.7 (5) |
C20—C15—C16—C17 | 0.9 (4) | C4C—C7C—C8C—C9C | −179.5 (2) |
S1—C15—C20—C19 | 178.62 (17) | C8C—C7C—C12C—C11C | 0.8 (4) |
C15—C16—C17—C18 | −0.3 (4) | C12C—C7C—C8C—C9C | 0.5 (4) |
C16—C17—C18—C19 | −1.5 (4) | C4C—C7C—C12C—C11C | −179.1 (2) |
C16—C17—C18—O11 | 178.0 (2) | C7C—C8C—C9C—N10C | −1.7 (4) |
O11—C18—C19—C20 | −176.9 (2) | N10C—C11C—C12C—C7C | −1.0 (4) |
C17—C18—C19—N11 | −177.3 (2) | N1A—C2A—C3A—C4A | −0.8 (6) |
O11—C18—C19—N11 | 3.1 (3) | C2A—C3A—C4A—C5A | 1.3 (5) |
C17—C18—C19—C20 | 2.7 (3) | C2A—C3A—C4A—C7A | −179.5 (3) |
N11—C19—C20—C14 | −0.8 (3) | C3A—C4A—C7A—C8A | 30.5 (4) |
N11—C19—C20—C15 | 178.0 (2) | C5A—C4A—C7A—C12A | 29.4 (4) |
C18—C19—C20—C14 | 179.2 (2) | C3A—C4A—C7A—C12A | −149.7 (3) |
C18—C19—C20—C15 | −2.1 (3) | C5A—C4A—C7A—C8A | −150.4 (3) |
N1—C2—C3—C4 | 0.3 (3) | C3A—C4A—C5A—C6A | −1.0 (4) |
C2—C3—C4—C10 | −0.5 (3) | C7A—C4A—C5A—C6A | 179.8 (3) |
C3—C4—C10—C9 | 0.2 (3) | C4A—C5A—C6A—N1A | 0.1 (6) |
C3—C4—C10—C5 | −179.65 (19) | C4A—C7A—C8A—C9A | −179.9 (3) |
S2—C5—C10—C9 | −178.33 (15) | C12A—C7A—C8A—C9A | 0.3 (4) |
C6—C5—C10—C9 | 0.5 (3) | C8A—C7A—C12A—C11A | −0.5 (4) |
S2—C5—C6—C7 | 178.38 (16) | C4A—C7A—C12A—C11A | 179.7 (3) |
C6—C5—C10—C4 | −179.59 (19) | C7A—C8A—C9A—N10A | 0.2 (5) |
S2—C5—C10—C4 | 1.5 (3) | N10A—C11A—C12A—C7A | 0.2 (5) |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x+2, −y+1, −z+1; (vi) x, y+1, z; (vii) −x+1, −y+2, −z+1; (viii) −x, −y+1, −z; (ix) −x+1, −y+1, −z; (x) −x, −y+1, −z+1; (xi) −x+1, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O4Wiii | 0.82 | 1.77 | 2.574 (3) | 168 |
N1B—H1B···O3Wix | 0.86 | 1.73 | 2.584 (3) | 172 |
N10C—H10C···N10Aiv | 0.86 | 1.86 | 2.717 (3) | 177 |
O1W—H11···O5Wiv | 0.88 | 1.93 | 2.802 (3) | 174 |
O11—H11′···N10Bvii | 0.82 | 1.89 | 2.690 (2) | 165 |
O1W—H12···O4i | 0.84 | 1.96 | 2.796 (4) | 176 |
O2W—H21···O1 | 0.82 | 2.58 | 2.991 (3) | 113 |
O2W—H22···N1Axii | 0.81 | 2.15 | 2.790 (4) | 136 |
O3W—H31···O2W | 0.88 | 1.73 | 2.580 (4) | 164 |
O3W—H32···O14ii | 0.86 | 1.83 | 2.679 (3) | 171 |
O4W—H41···N1Cix | 0.83 | 1.97 | 2.792 (3) | 170 |
O4W—H42···O5W | 0.84 | 1.91 | 2.736 (3) | 167 |
O5W—H51···O11 | 0.99 | 2.45 | 3.153 (3) | 127 |
O5W—H51···N11 | 0.99 | 1.82 | 2.761 (3) | 158 |
O5W—H52···O12ii | 0.86 | 2.00 | 2.848 (3) | 169 |
C8B—H8B···O1Wx | 0.93 | 2.46 | 3.312 (4) | 152 |
C9B—H9B···O1Wvi | 0.93 | 2.55 | 3.425 (4) | 156 |
C12C—H12C···O12ii | 0.93 | 2.29 | 3.210 (3) | 171 |
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (vi) x, y+1, z; (vii) −x+1, −y+2, −z+1; (ix) −x+1, −y+1, −z; (x) −x, −y+1, −z+1; (xii) −x+1, −y, −z. |
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