Brucinium toluene-4-sulfonate trihydrate at 130 K

Smith, G.; Wermuth, U.D.; Healy, P.C.; Young, D.J.; White, J.M.

doi:10.1107/S1600536805022695

Brucinium toluene-4-sulfonate trihydrate at 130 K

G. Smith, U. D. Wermuth, P. C. Healy, D. J. Young and J. M. White

The low-temperature (130 K) structure of the 1:1 proton-transfer compound of brucine with toluene-4-sulfonic acid (systematic name: 2,3-dimethoxy-10-oxostrychnidinium toluene-4-sulfonate trihydrate), C₂₃H₂₇N₂O₄⁺·C₇H₇O₃S^-·3H₂O, has been determined. The asymmetric unit contains two cations, two anions and six molecules of water. Brucinium cations form the familiar undulating head-to-tail ribbon structures, which associate with the toluene-4-sulfonate anions and the water molecules in the interstitial cavities through hydrogen-bonding associations involving all available donor and acceptor atoms on all species. The result is a framework polymer structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805022695/bt6697sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805022695/bt6697Isup2.hkl Contains datablock I

CCDC reference: 282245

checkCIF report

Key indicators

Single-crystal X-ray study
T = 130 K
Mean (C-C) = 0.004 Å
R factor = 0.049
wR factor = 0.088
Data-to-parameter ratio = 15.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    S1C    -   O11C    ..      12.34 su

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT213_ALERT_2_C Atom O11C    has ADP max/min Ratio .............       4.00 prolat
PLAT230_ALERT_2_C Hirshfeld Test Diff for    S1C    -   O12C    ..       5.68 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1C    -   C2C     ..       5.19 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C1C    -   C6C     ..       6.79 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C4D    -   C41D    ..       5.19 su
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.45
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.27
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..       0.06

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.58
           From the CIF: _reflns_number_total              12628
           Count of symmetry unique reflns         6886
           Completeness (_total/calc)            183.39%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      5742
           Fraction of Friedel pairs measured     0.834
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   9 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

2,3-dimethoxy-10-oxostrychnidinium toluene-4-sulfonate trihydrate top

Crystal data top

C₂₃H₂₇N₂O₄⁺·C₇H₇O₃S⁻·3H₂O	F(000) = 1320
M_r = 620.71	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁	Melting point = 486.5–488.8 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 12.1813 (9) Å	Cell parameters from 3782 reflections
b = 30.862 (2) Å	θ = 2.6–22.4°
c = 7.7875 (6) Å	µ = 0.17 mm⁻¹
β = 93.400 (2)°	T = 130 K
V = 2922.5 (4) Å³	Plate, colourless
Z = 4	0.50 × 0.30 × 0.05 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	8427 reflections with F² > 2σ(F²)
Radiation source: sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 27.6°, θ_min = 1.3°
φ and ω scans	h = −15→8
18490 measured reflections	k = −37→39
12628 independent reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.088	w = 1/[σ²(F_o²) + (0.0263P)²] where P = (F_o² + 2F_c²)/3
S = 0.84	(Δ/σ)_max = 0.003
12628 reflections	Δρ_max = 0.53 e Å⁻³
837 parameters	Δρ_min = −0.40 e Å⁻³
1 restraint	Absolute structure: Flack (1983), with 5742 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (6)

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 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	U_iso*/U_eq
O2A	−0.15731 (17)	0.81576 (6)	0.0727 (3)	0.0281 (8)
O3A	−0.04605 (16)	0.88564 (6)	0.0354 (3)	0.0276 (8)
O24A	0.54606 (16)	0.72857 (7)	0.0386 (3)	0.0268 (8)
O25A	0.36310 (18)	0.86199 (7)	0.0287 (3)	0.0373 (9)
N9A	0.2864 (2)	0.79565 (8)	−0.0247 (3)	0.0223 (8)
N19A	0.1939 (2)	0.65021 (8)	−0.0259 (4)	0.0299 (10)
C1A	0.0023 (3)	0.76996 (10)	0.0278 (4)	0.0220 (10)
C2A	−0.0488 (2)	0.80951 (10)	0.0418 (4)	0.0231 (10)
C3A	0.0139 (2)	0.84768 (10)	0.0242 (4)	0.0217 (10)
C4A	0.1249 (3)	0.84646 (10)	0.0014 (4)	0.0240 (11)
C5A	0.1734 (2)	0.80582 (10)	−0.0085 (4)	0.0206 (10)
C6A	0.1129 (2)	0.76799 (9)	0.0008 (4)	0.0208 (10)
C7A	0.1833 (2)	0.72906 (10)	−0.0334 (4)	0.0219 (10)
C8A	0.3009 (2)	0.74816 (9)	−0.0113 (4)	0.0232 (10)
C10A	0.3729 (3)	0.82242 (10)	0.0213 (4)	0.0280 (11)
C11A	0.4822 (2)	0.80086 (10)	0.0601 (4)	0.0255 (11)
C12A	0.4827 (2)	0.75516 (10)	0.1451 (4)	0.0245 (10)
C13A	0.3643 (2)	0.73957 (10)	0.1595 (4)	0.0314 (11)
C14A	0.3470 (3)	0.69354 (10)	0.2275 (4)	0.0274 (11)
C15A	0.2240 (3)	0.68935 (11)	0.2546 (4)	0.0306 (11)
C16A	0.1625 (2)	0.68956 (10)	0.0806 (4)	0.0251 (11)
C17A	0.1574 (3)	0.71073 (10)	−0.2152 (4)	0.0271 (11)
C18A	0.2126 (3)	0.66673 (10)	−0.2050 (4)	0.0310 (11)
C20A	0.2932 (3)	0.62626 (10)	0.0504 (5)	0.0336 (11)
C21A	0.3827 (3)	0.65802 (10)	0.1092 (4)	0.0283 (11)
C22A	0.4840 (3)	0.65407 (11)	0.0624 (4)	0.0326 (11)
C23A	0.5737 (3)	0.68653 (11)	0.1092 (4)	0.0318 (11)
C24A	−0.2187 (3)	0.77705 (10)	0.0980 (5)	0.0360 (13)
C31A	0.0156 (3)	0.92488 (9)	0.0180 (4)	0.0292 (11)
O2B	0.32798 (17)	0.78357 (7)	0.5612 (3)	0.0287 (8)
O3B	0.44452 (17)	0.71452 (6)	0.6165 (3)	0.0276 (8)
O24B	1.03002 (17)	0.87219 (7)	0.5967 (3)	0.0265 (7)
O25B	0.84723 (17)	0.73952 (7)	0.6070 (3)	0.0371 (9)
N9B	0.7775 (2)	0.80618 (8)	0.6585 (3)	0.0233 (8)
N19B	0.6886 (2)	0.95155 (8)	0.6572 (3)	0.0266 (9)
C1B	0.4884 (3)	0.83023 (10)	0.6056 (4)	0.0241 (10)
C2B	0.4382 (3)	0.79037 (10)	0.5932 (4)	0.0249 (11)
C3B	0.5030 (3)	0.75257 (10)	0.6191 (4)	0.0233 (10)
C4B	0.6150 (3)	0.75501 (10)	0.6420 (4)	0.0246 (10)
C5B	0.6641 (2)	0.79587 (10)	0.6445 (4)	0.0216 (10)
C6B	0.6017 (3)	0.83314 (10)	0.6322 (4)	0.0227 (10)
C7B	0.6742 (3)	0.87251 (10)	0.6637 (4)	0.0243 (10)
C8B	0.7913 (2)	0.85393 (9)	0.6409 (4)	0.0218 (10)
C10B	0.8600 (3)	0.77888 (10)	0.6123 (4)	0.0258 (11)
C11B	0.9663 (2)	0.80019 (10)	0.5694 (4)	0.0269 (11)
C12B	0.9598 (2)	0.84607 (10)	0.4869 (4)	0.0255 (11)
C13B	0.8413 (3)	0.86151 (10)	0.4700 (4)	0.0232 (11)
C14B	0.8187 (3)	0.90754 (10)	0.4005 (4)	0.0269 (11)
C15B	0.6930 (3)	0.91221 (11)	0.3755 (4)	0.0236 (10)
C16B	0.6455 (3)	0.91199 (10)	0.5506 (4)	0.0244 (10)
C17B	0.6658 (3)	0.89165 (10)	0.8465 (4)	0.0236 (10)
C18B	0.7225 (3)	0.93496 (10)	0.8353 (4)	0.0272 (11)
C20B	0.7808 (3)	0.97526 (10)	0.5756 (4)	0.0321 (11)
C21B	0.8645 (3)	0.94328 (10)	0.5172 (4)	0.0271 (11)
C22B	0.9694 (3)	0.94689 (10)	0.5683 (4)	0.0314 (11)
C23B	1.0553 (3)	0.91398 (10)	0.5280 (4)	0.0312 (11)
C24B	0.2617 (3)	0.82078 (11)	0.5183 (5)	0.0250 (10)
C31B	0.5083 (3)	0.67534 (10)	0.6273 (4)	0.0295 (11)
S1C	1.03143 (8)	0.55101 (3)	1.01878 (16)	0.0409 (4)
O11C	1.0277 (3)	0.54209 (9)	1.2015 (4)	0.0642 (14)
O12C	1.1228 (2)	0.53173 (11)	0.9480 (5)	0.0655 (16)
O13C	1.0212 (2)	0.59698 (8)	0.9854 (4)	0.0575 (10)
C1C	0.9118 (3)	0.52593 (10)	0.9208 (5)	0.0320 (11)
C2C	0.8315 (3)	0.51193 (11)	1.0195 (5)	0.0330 (12)
C3C	0.7410 (3)	0.49028 (11)	0.9440 (5)	0.0370 (14)
C4C	0.7318 (3)	0.48233 (10)	0.7697 (5)	0.0349 (13)
C5C	0.8125 (3)	0.49803 (10)	0.6703 (5)	0.0334 (11)
C6C	0.9041 (3)	0.51972 (10)	0.7429 (5)	0.0398 (14)
C41C	0.6345 (3)	0.45761 (12)	0.6915 (6)	0.0578 (16)
S1D	0.48722 (7)	0.53245 (3)	0.21291 (11)	0.0272 (3)
O11D	0.37679 (17)	0.54311 (7)	0.2624 (3)	0.0329 (8)
O12D	0.50990 (18)	0.48625 (7)	0.2502 (3)	0.0356 (8)
O13D	0.50791 (17)	0.54460 (7)	0.0389 (3)	0.0342 (8)
C1D	0.5798 (2)	0.56171 (10)	0.3530 (4)	0.0242 (10)
C2D	0.5643 (3)	0.56043 (10)	0.5276 (5)	0.0303 (11)
C3D	0.6365 (3)	0.58216 (11)	0.6417 (5)	0.0365 (12)
C4D	0.7241 (3)	0.60541 (10)	0.5830 (5)	0.0364 (13)
C5D	0.7386 (3)	0.60604 (11)	0.4073 (5)	0.0382 (14)
C6D	0.6669 (3)	0.58402 (10)	0.2911 (5)	0.0338 (13)
C41D	0.8028 (3)	0.62921 (12)	0.7082 (5)	0.0524 (16)
O1W	0.6644 (3)	0.41658 (10)	0.2716 (4)	0.0533 (11)
O2W	0.9784 (3)	0.68855 (11)	0.3966 (4)	0.0540 (11)
O3W	0.2871 (2)	0.58904 (9)	0.5338 (4)	0.0468 (11)
O4W	0.3270 (3)	0.52635 (10)	0.7984 (4)	0.0526 (11)
O5W	0.0608 (3)	0.60490 (10)	0.4609 (5)	0.0608 (14)
O6W	0.8722 (2)	0.66944 (10)	0.0849 (4)	0.0697 (12)
H1A	−0.038800	0.744000	0.036700	0.0260*
H4A	0.166700	0.872300	−0.007300	0.0290*
H8A	0.345100	0.737800	−0.107400	0.0280*
H12A	0.520100	0.756900	0.262700	0.0290*
H13A	0.331700	0.759400	0.244300	0.0270*
H14A	0.388800	0.690500	0.341200	0.0330*
H16A	0.081900	0.688000	0.098300	0.0300*
H19A	0.137 (2)	0.6339 (9)	−0.025 (3)	0.051 (9)*
H22A	0.501900	0.629500	−0.004200	0.0390*
H31A	0.527400	0.820300	0.136500	0.0310*
H32A	0.519500	0.798400	−0.049100	0.0310*
H33A	0.209500	0.662000	0.315900	0.0370*
H34A	0.199400	0.713800	0.324900	0.0370*
H35A	0.188900	0.729200	−0.303900	0.0320*
H36A	0.077100	0.708000	−0.240800	0.0320*
H37A	0.292200	0.669400	−0.222300	0.0370*
H38A	0.179100	0.646900	−0.293400	0.0370*
H39A	0.321400	0.606400	−0.036700	0.0400*
H40A	0.272000	0.608700	0.149400	0.0400*
H41A	0.584100	0.688700	0.235900	0.0380*
H42A	0.643700	0.676500	0.064300	0.0380*
H43A	−0.293900	0.784600	0.125000	0.0540*
H44A	−0.183600	0.760500	0.193500	0.0540*
H45A	−0.220600	0.759500	−0.007100	0.0540*
H46A	0.072900	0.926800	0.111500	0.0440*
H47A	−0.033800	0.949800	0.023500	0.0440*
H48A	0.049700	0.924800	−0.092800	0.0440*
H1B	0.445300	0.855900	0.596000	0.0290*
H4B	0.658200	0.729500	0.655900	0.0290*
H8B	0.802100	0.841400	0.386400	0.0280*
H12B	0.989700	0.844800	0.370200	0.0310*
H13B	0.842900	0.864800	0.736000	0.0260*
H14B	0.851100	0.910300	0.286000	0.0320*
H16B	0.563700	0.914200	0.534400	0.0290*
H19B	0.631 (2)	0.9680 (10)	0.670 (4)	0.048 (10)*
H22B	0.991900	0.971600	0.634100	0.0380*
H31B	1.003600	0.780800	0.490000	0.0320*
H32B	1.013900	0.802100	0.676700	0.0320*
H33B	0.662000	0.887900	0.305200	0.0340*
H34B	0.674000	0.939700	0.315100	0.0340*
H35B	0.588100	0.895200	0.874400	0.0280*
H36B	0.703800	0.872900	0.934500	0.0280*
H37B	0.698100	0.955000	0.924600	0.0330*
H38B	0.803300	0.931600	0.849800	0.0330*
H39B	0.750700	0.992300	0.475800	0.0380*
H40B	0.816500	0.995600	0.659800	0.0380*
H41B	1.128000	0.923600	0.577500	0.0370*
H42B	1.059600	0.911700	0.401800	0.0370*
H43B	0.187800	0.811400	0.477600	0.0600*
H44B	0.295100	0.837300	0.427500	0.0600*
H45B	0.256800	0.839100	0.620400	0.0600*
H46B	0.459200	0.650300	0.614700	0.0440*
H47B	0.559900	0.675000	0.535400	0.0440*
H48B	0.549500	0.674000	0.739200	0.0440*
H2C	0.837000	0.516800	1.140200	0.0400*
H3C	0.684300	0.480800	1.013900	0.0440*
H5C	0.805600	0.494000	0.549200	0.0400*
H6C	0.960000	0.530000	0.673300	0.0410*
H41C	0.640300	0.455400	0.566800	0.0690*
H42C	0.566500	0.472800	0.715500	0.0690*
H43C	0.633400	0.428500	0.741400	0.0690*
H2D	0.504200	0.544700	0.569100	0.0360*
H3D	0.625900	0.581100	0.761500	0.0440*
H5D	0.798600	0.621800	0.365600	0.0460*
H6D	0.678100	0.584400	0.171400	0.0410*
H41D	0.878500	0.620900	0.687500	0.0630*
H42D	0.793900	0.660500	0.691800	0.0630*
H43D	0.786800	0.621600	0.826300	0.0630*
H11W	0.667 (3)	0.4057 (14)	0.158 (6)	0.079 (17)*
H12W	0.627 (3)	0.4391 (14)	0.254 (5)	0.061 (15)*
H21W	0.936 (4)	0.7013 (17)	0.476 (7)	0.11 (2)*
H22W	1.000 (3)	0.6649 (14)	0.429 (5)	0.059 (16)*
H31W	0.316 (3)	0.5744 (15)	0.447 (6)	0.045 (16)*
H32W	0.291 (3)	0.5734 (12)	0.617 (5)	0.040 (13)*
H41W	0.389 (3)	0.5315 (13)	0.885 (5)	0.071 (14)*
H42W	0.271 (3)	0.5263 (12)	0.843 (5)	0.037 (13)*
H51W	0.129 (3)	0.5979 (13)	0.488 (5)	0.055 (14)*
H52W	0.033 (3)	0.5935 (14)	0.366 (6)	0.069 (16)*
H61W	0.907 (3)	0.6757 (14)	0.187 (6)	0.080 (16)*
H62W	0.917 (3)	0.6478 (14)	0.055 (6)	0.075 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2A	0.0213 (13)	0.0213 (12)	0.0421 (14)	−0.0009 (9)	0.0055 (10)	−0.0044 (11)
O3A	0.0282 (14)	0.0155 (11)	0.0395 (14)	0.0012 (10)	0.0044 (11)	−0.0019 (10)
O24A	0.0234 (13)	0.0258 (13)	0.0316 (13)	0.0019 (10)	0.0054 (10)	0.0040 (10)
O25A	0.0310 (14)	0.0188 (13)	0.0622 (17)	−0.0034 (10)	0.0037 (12)	−0.0034 (12)
N9A	0.0223 (15)	0.0145 (13)	0.0302 (15)	−0.0017 (11)	0.0019 (12)	−0.0003 (12)
N19A	0.0311 (17)	0.0179 (15)	0.0403 (18)	0.0053 (12)	−0.0016 (13)	−0.0008 (13)
C1A	0.0261 (18)	0.0163 (16)	0.0233 (18)	−0.0059 (13)	−0.0006 (14)	0.0014 (14)
C2A	0.0179 (18)	0.0249 (18)	0.0264 (18)	−0.0008 (14)	0.0002 (14)	−0.0029 (15)
C3A	0.0249 (18)	0.0173 (16)	0.0230 (18)	0.0025 (14)	0.0028 (14)	−0.0009 (14)
C4A	0.0265 (19)	0.0173 (17)	0.0282 (19)	−0.0038 (14)	0.0020 (15)	−0.0027 (14)
C5A	0.0173 (17)	0.0233 (17)	0.0213 (17)	−0.0007 (13)	0.0021 (13)	0.0023 (14)
C6A	0.0213 (18)	0.0185 (16)	0.0223 (18)	−0.0018 (13)	−0.0011 (14)	−0.0018 (14)
C7A	0.0206 (18)	0.0189 (16)	0.0263 (18)	−0.0001 (13)	0.0030 (14)	0.0002 (14)
C8A	0.0263 (19)	0.0141 (16)	0.0298 (19)	0.0008 (13)	0.0065 (14)	0.0018 (14)
C10A	0.032 (2)	0.0198 (18)	0.033 (2)	−0.0042 (15)	0.0086 (16)	−0.0036 (15)
C11A	0.0187 (18)	0.0254 (18)	0.0322 (19)	−0.0038 (14)	−0.0003 (14)	−0.0003 (15)
C12A	0.0237 (18)	0.0274 (18)	0.0225 (18)	−0.0052 (15)	0.0014 (14)	−0.0022 (15)
C13A	0.037 (2)	0.0174 (17)	0.040 (2)	−0.0009 (15)	0.0052 (17)	0.0048 (16)
C14A	0.0263 (19)	0.0286 (19)	0.0265 (18)	−0.0035 (15)	−0.0044 (15)	0.0093 (16)
C15A	0.032 (2)	0.0253 (18)	0.035 (2)	−0.0045 (15)	0.0050 (16)	0.0103 (16)
C16A	0.0193 (18)	0.0206 (17)	0.036 (2)	−0.0043 (14)	0.0063 (15)	0.0023 (15)
C17A	0.0278 (19)	0.0203 (17)	0.033 (2)	−0.0003 (14)	−0.0009 (15)	−0.0052 (15)
C18A	0.034 (2)	0.0214 (18)	0.037 (2)	0.0027 (15)	−0.0027 (16)	−0.0122 (16)
C20A	0.028 (2)	0.0215 (19)	0.051 (2)	0.0062 (15)	−0.0010 (17)	0.0043 (17)
C21A	0.029 (2)	0.0193 (17)	0.036 (2)	0.0020 (15)	−0.0019 (16)	0.0068 (15)
C22A	0.034 (2)	0.0212 (19)	0.042 (2)	0.0104 (15)	−0.0023 (17)	0.0090 (16)
C23A	0.0251 (19)	0.034 (2)	0.036 (2)	0.0098 (16)	0.0001 (15)	0.0065 (17)
C24A	0.0155 (18)	0.031 (2)	0.062 (3)	−0.0070 (15)	0.0057 (17)	−0.0009 (18)
C31A	0.033 (2)	0.0173 (17)	0.037 (2)	−0.0020 (15)	−0.0003 (16)	−0.0008 (15)
O2B	0.0217 (13)	0.0235 (12)	0.0406 (14)	0.0010 (10)	0.0003 (10)	−0.0054 (10)
O3B	0.0268 (13)	0.0196 (12)	0.0366 (14)	−0.0022 (10)	0.0026 (10)	−0.0048 (10)
O24B	0.0252 (13)	0.0212 (12)	0.0332 (13)	−0.0014 (10)	0.0019 (10)	0.0030 (10)
O25B	0.0293 (14)	0.0174 (12)	0.0655 (18)	0.0042 (10)	0.0098 (12)	−0.0018 (12)
N9B	0.0258 (15)	0.0154 (13)	0.0288 (15)	0.0023 (11)	0.0032 (12)	0.0025 (12)
N19B	0.0341 (17)	0.0168 (14)	0.0283 (16)	−0.0038 (12)	−0.0031 (13)	−0.0001 (12)
C1B	0.0225 (18)	0.0211 (17)	0.0288 (19)	0.0089 (14)	0.0030 (14)	−0.0003 (14)
C2B	0.0236 (19)	0.0292 (19)	0.0221 (17)	−0.0042 (15)	0.0036 (14)	−0.0062 (15)
C3B	0.0268 (19)	0.0205 (17)	0.0230 (18)	0.0000 (14)	0.0054 (14)	−0.0046 (14)
C4B	0.030 (2)	0.0184 (16)	0.0255 (18)	0.0050 (14)	0.0037 (14)	−0.0023 (14)
C5B	0.0165 (17)	0.0238 (17)	0.0244 (18)	−0.0006 (13)	0.0005 (14)	−0.0021 (14)
C6B	0.0241 (19)	0.0212 (17)	0.0231 (18)	0.0025 (14)	0.0037 (14)	−0.0027 (14)
C7B	0.0224 (18)	0.0199 (17)	0.0306 (19)	0.0048 (14)	0.0014 (14)	0.0010 (15)
C8B	0.0230 (18)	0.0153 (16)	0.0271 (18)	0.0006 (13)	0.0010 (14)	−0.0025 (14)
C10B	0.0253 (19)	0.0202 (19)	0.032 (2)	0.0070 (14)	0.0016 (15)	0.0023 (15)
C11B	0.0206 (18)	0.0242 (18)	0.036 (2)	0.0030 (14)	0.0025 (15)	−0.0028 (15)
C12B	0.0206 (18)	0.0292 (18)	0.0271 (19)	−0.0003 (15)	0.0036 (14)	−0.0014 (15)
C13B	0.0290 (19)	0.0180 (19)	0.0224 (18)	0.0032 (14)	−0.0004 (14)	−0.0006 (14)
C14B	0.030 (2)	0.0283 (19)	0.0227 (18)	0.0014 (15)	0.0050 (14)	0.0042 (15)
C15B	0.0245 (18)	0.0228 (17)	0.0238 (18)	0.0024 (14)	0.0045 (14)	0.0001 (14)
C16B	0.0200 (18)	0.0217 (17)	0.0310 (19)	0.0043 (14)	−0.0022 (14)	−0.0011 (15)
C17B	0.0245 (18)	0.0228 (17)	0.0238 (18)	0.0024 (14)	0.0045 (14)	0.0001 (14)
C18B	0.029 (2)	0.0229 (18)	0.030 (2)	0.0026 (14)	0.0040 (15)	−0.0061 (15)
C20B	0.035 (2)	0.0188 (18)	0.042 (2)	0.0009 (15)	−0.0024 (16)	0.0088 (16)
C21B	0.030 (2)	0.0196 (17)	0.032 (2)	0.0025 (14)	0.0037 (14)	0.0097 (15)
C22B	0.037 (2)	0.0174 (17)	0.040 (2)	−0.0009 (15)	0.0052 (17)	0.0048 (16)
C23B	0.028 (2)	0.0281 (19)	0.038 (2)	−0.0062 (15)	0.0073 (16)	0.0084 (16)
C24B	0.030 (2)	0.0189 (16)	0.0263 (18)	−0.0001 (13)	0.0030 (14)	0.0002 (14)
C31B	0.029 (2)	0.0224 (18)	0.037 (2)	0.0028 (14)	0.0017 (16)	0.0037 (15)
S1C	0.0394 (6)	0.0246 (5)	0.0589 (7)	0.0055 (4)	−0.0199 (5)	−0.0029 (5)
O11C	0.069 (2)	0.053 (2)	0.070 (2)	0.0326 (18)	−0.057 (2)	−0.0203 (17)
O12C	0.0281 (17)	0.087 (3)	0.078 (3)	0.0087 (17)	−0.0053 (19)	0.051 (3)
O13C	0.0485 (18)	0.0290 (15)	0.092 (2)	0.0139 (13)	−0.0210 (15)	−0.0090 (15)
C1C	0.033 (2)	0.0158 (17)	0.046 (2)	−0.0020 (15)	−0.0076 (17)	−0.0007 (16)
C2C	0.038 (2)	0.029 (2)	0.032 (2)	−0.0081 (17)	0.0025 (17)	0.0022 (16)
C3C	0.034 (2)	0.026 (2)	0.052 (3)	−0.0038 (16)	0.0119 (19)	−0.0059 (18)
C4C	0.036 (2)	0.0165 (18)	0.051 (3)	−0.0002 (15)	−0.0077 (18)	0.0001 (17)
C5C	0.046 (2)	0.0233 (19)	0.030 (2)	−0.0077 (17)	−0.0064 (18)	0.0052 (16)
C6C	0.021 (2)	0.030 (2)	0.068 (3)	0.0044 (16)	−0.0004 (18)	−0.0066 (19)
C41C	0.053 (3)	0.031 (2)	0.086 (3)	0.0135 (19)	−0.024 (2)	−0.010 (2)
S1D	0.0248 (5)	0.0199 (4)	0.0370 (5)	0.0007 (4)	0.0036 (4)	−0.0026 (4)
O11D	0.0251 (13)	0.0279 (14)	0.0456 (15)	−0.0004 (10)	0.0021 (11)	0.0041 (11)
O12D	0.0327 (15)	0.0202 (12)	0.0536 (16)	−0.0008 (10)	−0.0002 (12)	−0.0070 (11)
O13D	0.0383 (14)	0.0258 (13)	0.0388 (15)	0.0068 (10)	0.0055 (11)	−0.0027 (11)
C1D	0.0187 (17)	0.0149 (16)	0.039 (2)	−0.0013 (13)	0.0029 (14)	−0.0034 (15)
C2D	0.0233 (19)	0.0187 (17)	0.049 (2)	−0.0001 (14)	0.0019 (16)	−0.0024 (16)
C3D	0.036 (2)	0.031 (2)	0.042 (2)	−0.0110 (17)	−0.0026 (18)	0.0036 (18)
C4D	0.033 (2)	0.0164 (18)	0.058 (3)	−0.0025 (15)	−0.0120 (19)	0.0003 (18)
C5D	0.029 (2)	0.024 (2)	0.061 (3)	0.0071 (15)	−0.0025 (19)	−0.0126 (19)
C6D	0.030 (2)	0.0201 (18)	0.052 (3)	−0.0045 (15)	0.0080 (18)	−0.0096 (17)
C41D	0.051 (3)	0.031 (2)	0.073 (3)	0.0067 (19)	−0.016 (2)	0.001 (2)
O1W	0.064 (2)	0.0332 (17)	0.063 (2)	−0.0133 (15)	0.0056 (16)	−0.0077 (16)
O2W	0.054 (2)	0.0392 (19)	0.071 (2)	0.0031 (16)	0.0221 (17)	−0.0081 (18)
O3W	0.0486 (19)	0.0359 (17)	0.056 (2)	−0.0112 (13)	0.0029 (15)	0.0051 (16)
O4W	0.047 (2)	0.063 (2)	0.0468 (19)	0.0008 (17)	−0.0053 (17)	0.0104 (16)
O5W	0.055 (2)	0.051 (2)	0.075 (3)	−0.0111 (17)	−0.0081 (19)	0.0178 (18)
O6W	0.072 (2)	0.064 (2)	0.073 (2)	0.0047 (16)	0.0030 (17)	0.0007 (16)

Geometric parameters (Å, º) top

S1C—C1C	1.781 (4)	C20A—H40A	0.9891
S1C—O13C	1.446 (3)	C22A—H22A	0.9513
S1C—O12C	1.403 (3)	C23A—H41A	0.9896
S1C—O11C	1.453 (3)	C23A—H42A	0.9902
S1D—C1D	1.770 (3)	C24A—H43A	0.9800
S1D—O12D	1.478 (2)	C24A—H44A	0.9793
S1D—O13D	1.443 (2)	C24A—H45A	0.9806
S1D—O11D	1.459 (2)	C31A—H46A	0.9801
O2A—C2A	1.371 (3)	C31A—H47A	0.9790
O2A—C24A	1.429 (4)	C31A—H48A	0.9796
O3A—C3A	1.386 (3)	C1B—C6B	1.386 (5)
O3A—C31A	1.436 (4)	C1B—C2B	1.375 (5)
O24A—C23A	1.441 (4)	C2B—C3B	1.416 (5)
O24A—C12A	1.426 (4)	C3B—C4B	1.367 (5)
O25A—C10A	1.229 (4)	C4B—C5B	1.395 (4)
O2B—C2B	1.367 (4)	C5B—C6B	1.379 (4)
O2B—C24B	1.432 (4)	C6B—C7B	1.514 (5)
O3B—C3B	1.373 (4)	C7B—C17B	1.550 (4)
O3B—C31B	1.437 (4)	C7B—C16B	1.532 (4)
O24B—C23B	1.437 (4)	C7B—C8B	1.557 (4)
O24B—C12B	1.423 (4)	C8B—C13B	1.514 (4)
O25B—C10B	1.225 (4)	C10B—C11B	1.507 (4)
O1W—H11W	0.95 (5)	C11B—C12B	1.555 (4)
O1W—H12W	0.84 (4)	C12B—C13B	1.518 (4)
N9A—C10A	1.370 (4)	C13B—C14B	1.539 (4)
N9A—C8A	1.479 (4)	C14B—C21B	1.514 (4)
N9A—C5A	1.425 (3)	C14B—C15B	1.539 (5)
N19A—C18A	1.515 (4)	C15B—C16B	1.513 (5)
N19A—C20A	1.509 (4)	C17B—C18B	1.509 (5)
N19A—C16A	1.532 (4)	C20B—C21B	1.508 (5)
O2W—H21W	0.92 (5)	C21B—C22B	1.320 (5)
O2W—H22W	0.81 (4)	C22B—C23B	1.505 (5)
N19A—H19A	0.86 (3)	C1B—H1B	0.9509
N9B—C8B	1.490 (4)	C4B—H4B	0.9496
N9B—C10B	1.376 (4)	C8B—H13B	1.0004
N9B—C5B	1.415 (3)	C11B—H31B	0.9901
N19B—C20B	1.512 (4)	C11B—H32B	0.9902
N19B—C16B	1.550 (4)	C12B—H12B	0.9997
N19B—C18B	1.513 (4)	C13B—H8B	1.0001
O3W—H31W	0.90 (4)	C14B—H14B	0.9999
O3W—H32W	0.81 (4)	C15B—H34B	0.9908
N19B—H19B	0.88 (3)	C15B—H33B	0.9903
O4W—H41W	1.00 (4)	C16B—H16B	0.9993
O4W—H42W	0.78 (4)	C17B—H35B	0.9897
O5W—H52W	0.87 (5)	C17B—H36B	0.9905
O5W—H51W	0.87 (4)	C18B—H38B	0.9895
O6W—H62W	0.90 (4)	C18B—H37B	0.9894
O6W—H61W	0.90 (4)	C20B—H39B	0.9906
C1A—C6A	1.377 (4)	C20B—H40B	0.9896
C1A—C2A	1.377 (4)	C22B—H22B	0.9500
C2A—C3A	1.415 (4)	C23B—H42B	0.9898
C3A—C4A	1.375 (4)	C23B—H41B	0.9902
C4A—C5A	1.390 (4)	C24B—H44B	0.9796
C5A—C6A	1.385 (4)	C24B—H45B	0.9803
C6A—C7A	1.509 (4)	C24B—H43B	0.9802
C7A—C17A	1.540 (4)	C31B—H47B	0.9802
C7A—C8A	1.549 (4)	C31B—H46B	0.9786
C7A—C16A	1.538 (4)	C31B—H48B	0.9803
C8A—C13A	1.521 (4)	C1C—C2C	1.350 (5)
C10A—C11A	1.503 (4)	C1C—C6C	1.396 (5)
C11A—C12A	1.558 (4)	C2C—C3C	1.389 (5)
C12A—C13A	1.531 (4)	C3C—C4C	1.377 (5)
C13A—C14A	1.535 (4)	C4C—C41C	1.507 (5)
C14A—C21A	1.512 (4)	C4C—C5C	1.375 (5)
C14A—C15A	1.531 (5)	C5C—C6C	1.392 (5)
C15A—C16A	1.509 (4)	C2C—H2C	0.9503
C17A—C18A	1.515 (5)	C3C—H3C	0.9506
C20A—C21A	1.517 (5)	C5C—H5C	0.9500
C21A—C22A	1.313 (5)	C6C—H6C	0.9497
C22A—C23A	1.511 (5)	C41C—H41C	0.9802
C1A—H1A	0.9494	C41C—H42C	0.9794
C4A—H4A	0.9507	C41C—H43C	0.9792
C8A—H8A	1.0000	C1D—C2D	1.384 (5)
C11A—H32A	0.9906	C1D—C6D	1.376 (4)
C11A—H31A	0.9891	C2D—C3D	1.386 (5)
C12A—H12A	0.9998	C3D—C4D	1.386 (5)
C13A—H13A	0.9997	C4D—C5D	1.390 (5)
C14A—H14A	0.9993	C4D—C41D	1.516 (5)
C15A—H34A	0.9891	C5D—C6D	1.396 (5)
C15A—H33A	0.9907	C2D—H2D	0.9509
C16A—H16A	1.0007	C3D—H3D	0.9500
C17A—H35A	0.9903	C5D—H5D	0.9510
C17A—H36A	0.9902	C6D—H6D	0.9501
C18A—H38A	0.9908	C41D—H42D	0.9793
C18A—H37A	0.9903	C41D—H43D	0.9799
C20A—H39A	0.9906	C41D—H41D	0.9796

O13C—S1C—C1C	106.84 (16)	O2B—C2B—C3B	115.6 (3)
O11C—S1C—O13C	110.77 (18)	O3B—C3B—C2B	114.7 (3)
O11C—S1C—C1C	105.36 (19)	O3B—C3B—C4B	124.2 (3)
O11C—S1C—O12C	112.1 (2)	C2B—C3B—C4B	121.1 (3)
O12C—S1C—C1C	107.17 (19)	C3B—C4B—C5B	118.4 (3)
O12C—S1C—O13C	114.03 (19)	C4B—C5B—C6B	121.3 (3)
O12D—S1D—O13D	113.22 (14)	N9B—C5B—C6B	110.4 (3)
O11D—S1D—C1D	106.62 (13)	N9B—C5B—C4B	128.3 (3)
O11D—S1D—O13D	113.88 (14)	C5B—C6B—C7B	110.1 (3)
O12D—S1D—C1D	105.44 (14)	C1B—C6B—C7B	130.0 (3)
O11D—S1D—O12D	109.28 (13)	C1B—C6B—C5B	119.7 (3)
O13D—S1D—C1D	107.82 (14)	C6B—C7B—C8B	102.4 (2)
C2A—O2A—C24A	115.1 (2)	C6B—C7B—C16B	115.7 (3)
C3A—O3A—C31A	115.3 (2)	C16B—C7B—C17B	101.5 (2)
C12A—O24A—C23A	114.7 (2)	C8B—C7B—C17B	110.8 (3)
C2B—O2B—C24B	117.0 (2)	C6B—C7B—C17B	112.6 (3)
C3B—O3B—C31B	116.1 (2)	C8B—C7B—C16B	114.0 (3)
C12B—O24B—C23B	114.8 (2)	N9B—C8B—C7B	104.2 (2)
H11W—O1W—H12W	101 (4)	N9B—C8B—C13B	106.7 (2)
C5A—N9A—C10A	125.2 (3)	C7B—C8B—C13B	117.5 (3)
C5A—N9A—C8A	108.9 (2)	O25B—C10B—C11B	122.3 (3)
C8A—N9A—C10A	119.5 (2)	N9B—C10B—C11B	116.2 (3)
C16A—N19A—C20A	113.3 (3)	O25B—C10B—N9B	121.5 (3)
C18A—N19A—C20A	111.5 (3)	C10B—C11B—C12B	117.7 (2)
C16A—N19A—C18A	106.7 (2)	C11B—C12B—C13B	110.3 (2)
H21W—O2W—H22W	111 (4)	O24B—C12B—C13B	114.1 (2)
C16A—N19A—H19A	103.5 (18)	O24B—C12B—C11B	104.7 (2)
C18A—N19A—H19A	111.8 (16)	C8B—C13B—C12B	107.8 (2)
C20A—N19A—H19A	109.8 (18)	C8B—C13B—C14B	112.3 (3)
C8B—N9B—C10B	119.6 (2)	C12B—C13B—C14B	118.0 (3)
C5B—N9B—C8B	109.3 (2)	C15B—C14B—C21B	109.6 (3)
C5B—N9B—C10B	124.5 (3)	C13B—C14B—C21B	114.2 (3)
C16B—N19B—C18B	106.8 (2)	C13B—C14B—C15B	106.7 (3)
C18B—N19B—C20B	112.3 (2)	C14B—C15B—C16B	108.5 (3)
C16B—N19B—C20B	113.1 (2)	C7B—C16B—C15B	115.8 (3)
H31W—O3W—H32W	107 (4)	N19B—C16B—C15B	110.1 (3)
C20B—N19B—H19B	112.8 (19)	N19B—C16B—C7B	105.1 (2)
C16B—N19B—H19B	105.6 (19)	C7B—C17B—C18B	103.2 (3)
C18B—N19B—H19B	106 (2)	N19B—C18B—C17B	104.6 (2)
H41W—O4W—H42W	110 (4)	N19B—C20B—C21B	110.0 (2)
H51W—O5W—H52W	115 (4)	C14B—C21B—C22B	123.9 (3)
H61W—O6W—H62W	97 (4)	C20B—C21B—C22B	120.9 (3)
C2A—C1A—C6A	120.1 (3)	C14B—C21B—C20B	115.2 (3)
O2A—C2A—C1A	125.7 (3)	C21B—C22B—C23B	123.6 (3)
C1A—C2A—C3A	118.8 (3)	O24B—C23B—C22B	111.2 (3)
O2A—C2A—C3A	115.6 (2)	C6B—C1B—H1B	119.86
C2A—C3A—C4A	122.0 (3)	C2B—C1B—H1B	119.92
O3A—C3A—C2A	114.1 (2)	C5B—C4B—H4B	120.90
O3A—C3A—C4A	123.9 (3)	C3B—C4B—H4B	120.74
C3A—C4A—C5A	117.1 (3)	N9B—C8B—H13B	109.44
C4A—C5A—C6A	121.9 (3)	C13B—C8B—H13B	109.33
N9A—C5A—C6A	109.8 (2)	C7B—C8B—H13B	109.37
N9A—C5A—C4A	128.3 (3)	C12B—C11B—H32B	107.90
C1A—C6A—C5A	119.9 (3)	C12B—C11B—H31B	107.84
C5A—C6A—C7A	110.6 (2)	C10B—C11B—H31B	107.87
C1A—C6A—C7A	129.3 (3)	H31B—C11B—H32B	107.19
C8A—C7A—C16A	114.9 (2)	C10B—C11B—H32B	107.86
C6A—C7A—C17A	111.5 (2)	O24B—C12B—H12B	109.27
C6A—C7A—C16A	114.5 (2)	C13B—C12B—H12B	109.22
C16A—C7A—C17A	102.0 (2)	C11B—C12B—H12B	109.12
C6A—C7A—C8A	102.1 (2)	C12B—C13B—H8B	106.05
C8A—C7A—C17A	112.3 (2)	C8B—C13B—H8B	105.95
C7A—C8A—C13A	116.7 (2)	C14B—C13B—H8B	105.98
N9A—C8A—C13A	106.7 (2)	C15B—C14B—H14B	108.76
N9A—C8A—C7A	105.3 (2)	C13B—C14B—H14B	108.69
O25A—C10A—N9A	122.4 (3)	C21B—C14B—H14B	108.80
N9A—C10A—C11A	116.4 (3)	H33B—C15B—H34B	108.40
O25A—C10A—C11A	121.2 (3)	C16B—C15B—H34B	109.92
C10A—C11A—C12A	117.9 (2)	C14B—C15B—H34B	110.06
O24A—C12A—C13A	114.0 (2)	C14B—C15B—H33B	110.06
O24A—C12A—C11A	105.2 (2)	C16B—C15B—H33B	109.95
C11A—C12A—C13A	109.6 (2)	N19B—C16B—H16B	108.50
C8A—C13A—C14A	113.0 (2)	C7B—C16B—H16B	108.59
C8A—C13A—C12A	108.2 (2)	C15B—C16B—H16B	108.53
C12A—C13A—C14A	117.7 (2)	H35B—C17B—H36B	109.06
C13A—C14A—C21A	114.2 (3)	C18B—C17B—H35B	111.19
C15A—C14A—C21A	110.0 (3)	C7B—C17B—H36B	111.05
C13A—C14A—C15A	106.3 (3)	C18B—C17B—H36B	111.14
C14A—C15A—C16A	108.3 (2)	C7B—C17B—H35B	111.09
C7A—C16A—C15A	115.6 (2)	N19B—C18B—H37B	110.84
N19A—C16A—C15A	110.9 (2)	N19B—C18B—H38B	110.84
N19A—C16A—C7A	105.1 (2)	C17B—C18B—H37B	110.81
C7A—C17A—C18A	102.4 (2)	H37B—C18B—H38B	108.88
N19A—C18A—C17A	105.0 (2)	C17B—C18B—H38B	110.86
N19A—C20A—C21A	110.3 (2)	C21B—C20B—H39B	109.64
C14A—C21A—C22A	123.0 (3)	N19B—C20B—H40B	109.68
C20A—C21A—C22A	121.8 (3)	C21B—C20B—H40B	109.66
C14A—C21A—C20A	115.1 (3)	H39B—C20B—H40B	108.11
C21A—C22A—C23A	123.3 (3)	N19B—C20B—H39B	109.70
O24A—C23A—C22A	110.8 (3)	C23B—C22B—H22B	118.19
C6A—C1A—H1A	119.92	C21B—C22B—H22B	118.25
C2A—C1A—H1A	119.95	H41B—C23B—H42B	108.00
C5A—C4A—H4A	121.44	O24B—C23B—H42B	109.33
C3A—C4A—H4A	121.42	C22B—C23B—H41B	109.47
N9A—C8A—H8A	109.35	C22B—C23B—H42B	109.48
C13A—C8A—H8A	109.31	O24B—C23B—H41B	109.31
C7A—C8A—H8A	109.30	H44B—C24B—H45B	109.46
C12A—C11A—H31A	107.79	H43B—C24B—H45B	109.49
H31A—C11A—H32A	107.19	O2B—C24B—H45B	109.51
C12A—C11A—H32A	107.76	H43B—C24B—H44B	109.46
C10A—C11A—H31A	107.90	O2B—C24B—H44B	109.47
C10A—C11A—H32A	107.90	O2B—C24B—H43B	109.45
C13A—C12A—H12A	109.26	O3B—C31B—H46B	109.48
O24A—C12A—H12A	109.31	O3B—C31B—H47B	109.52
C11A—C12A—H12A	109.31	H46B—C31B—H47B	109.45
C14A—C13A—H13A	105.70	H47B—C31B—H48B	109.39
C8A—C13A—H13A	105.66	O3B—C31B—H48B	109.51
C12A—C13A—H13A	105.60	H46B—C31B—H48B	109.48
C21A—C14A—H14A	108.78	C2C—C1C—C6C	120.8 (3)
C15A—C14A—H14A	108.74	S1C—C1C—C2C	119.8 (3)
C13A—C14A—H14A	108.63	S1C—C1C—C6C	119.3 (3)
C16A—C15A—H33A	110.07	C1C—C2C—C3C	119.8 (4)
H33A—C15A—H34A	108.35	C2C—C3C—C4C	121.3 (3)
C14A—C15A—H34A	110.06	C3C—C4C—C5C	118.2 (3)
C14A—C15A—H33A	110.02	C3C—C4C—C41C	120.3 (3)
C16A—C15A—H34A	110.07	C5C—C4C—C41C	121.5 (4)
N19A—C16A—H16A	108.36	C4C—C5C—C6C	121.6 (4)
C15A—C16A—H16A	108.36	C1C—C6C—C5C	118.3 (3)
C7A—C16A—H16A	108.31	C1C—C2C—H2C	120.09
C7A—C17A—H36A	111.25	C3C—C2C—H2C	120.15
H35A—C17A—H36A	109.12	C4C—C3C—H3C	119.35
C18A—C17A—H36A	111.36	C2C—C3C—H3C	119.40
C7A—C17A—H35A	111.29	C4C—C5C—H5C	119.25
C18A—C17A—H35A	111.30	C6C—C5C—H5C	119.19
C17A—C18A—H38A	110.73	C5C—C6C—H6C	120.89
H37A—C18A—H38A	108.85	C1C—C6C—H6C	120.81
C17A—C18A—H37A	110.69	C4C—C41C—H41C	109.53
N19A—C18A—H38A	110.71	C4C—C41C—H43C	109.45
N19A—C18A—H37A	110.80	H42C—C41C—H43C	109.38
C21A—C20A—H40A	109.57	C4C—C41C—H42C	109.53
N19A—C20A—H39A	109.62	H41C—C41C—H42C	109.50
H39A—C20A—H40A	108.17	H41C—C41C—H43C	109.44
C21A—C20A—H39A	109.53	S1D—C1D—C6D	121.1 (3)
N19A—C20A—H40A	109.57	S1D—C1D—C2D	118.2 (2)
C23A—C22A—H22A	118.30	C2D—C1D—C6D	120.8 (3)
C21A—C22A—H22A	118.36	C1D—C2D—C3D	119.8 (3)
C22A—C23A—H41A	109.47	C2D—C3D—C4D	120.7 (4)
O24A—C23A—H41A	109.43	C5D—C4D—C41D	120.9 (3)
C22A—C23A—H42A	109.46	C3D—C4D—C5D	118.5 (3)
O24A—C23A—H42A	109.47	C3D—C4D—C41D	120.6 (3)
H41A—C23A—H42A	108.13	C4D—C5D—C6D	121.3 (3)
O2A—C24A—H45A	109.47	C1D—C6D—C5D	118.8 (3)
H43A—C24A—H44A	109.43	C1D—C2D—H2D	120.07
H43A—C24A—H45A	109.53	C3D—C2D—H2D	120.09
O2A—C24A—H44A	109.40	C4D—C3D—H3D	119.60
H44A—C24A—H45A	109.48	C2D—C3D—H3D	119.67
O2A—C24A—H43A	109.52	C4D—C5D—H5D	119.23
O3A—C31A—H46A	109.53	C6D—C5D—H5D	119.44
H46A—C31A—H47A	109.42	C1D—C6D—H6D	120.56
H47A—C31A—H48A	109.53	C5D—C6D—H6D	120.60
O3A—C31A—H48A	109.42	H42D—C41D—H43D	109.40
O3A—C31A—H47A	109.40	C4D—C41D—H41D	109.44
H46A—C31A—H48A	109.51	C4D—C41D—H42D	109.45
C2B—C1B—C6B	120.2 (3)	C4D—C41D—H43D	109.52
C1B—C2B—C3B	119.0 (3)	H41D—C41D—H42D	109.55
O2B—C2B—C1B	125.3 (3)	H41D—C41D—H43D	109.47

O11C—S1C—C1C—C6C	−165.0 (3)	C10A—C11A—C12A—O24A	127.5 (3)
O12C—S1C—C1C—C6C	−45.4 (3)	C11A—C12A—C13A—C8A	45.8 (3)
O13C—S1C—C1C—C6C	77.2 (3)	O24A—C12A—C13A—C8A	−71.8 (3)
O11C—S1C—C1C—C2C	12.9 (3)	C11A—C12A—C13A—C14A	175.4 (3)
O12C—S1C—C1C—C2C	132.4 (3)	O24A—C12A—C13A—C14A	57.8 (4)
O13C—S1C—C1C—C2C	−105.0 (3)	C8A—C13A—C14A—C21A	60.2 (4)
O13D—S1D—C1D—C2D	170.3 (2)	C8A—C13A—C14A—C15A	−61.3 (3)
O11D—S1D—C1D—C6D	−134.4 (3)	C12A—C13A—C14A—C15A	171.4 (3)
O12D—S1D—C1D—C6D	109.5 (3)	C12A—C13A—C14A—C21A	−67.1 (4)
O11D—S1D—C1D—C2D	47.6 (3)	C13A—C14A—C21A—C20A	−121.4 (3)
O12D—S1D—C1D—C2D	−68.5 (3)	C21A—C14A—C15A—C16A	−55.5 (3)
O13D—S1D—C1D—C6D	−11.8 (3)	C13A—C14A—C15A—C16A	68.7 (3)
C24A—O2A—C2A—C1A	2.4 (4)	C15A—C14A—C21A—C22A	179.3 (3)
C24A—O2A—C2A—C3A	−177.3 (3)	C15A—C14A—C21A—C20A	−2.0 (4)
C31A—O3A—C3A—C4A	1.2 (4)	C13A—C14A—C21A—C22A	59.8 (4)
C31A—O3A—C3A—C2A	180.0 (19)	C14A—C15A—C16A—C7A	−56.1 (3)
C12A—O24A—C23A—C22A	87.6 (3)	C14A—C15A—C16A—N19A	63.4 (3)
C23A—O24A—C12A—C13A	−70.2 (3)	C7A—C17A—C18A—N19A	37.8 (3)
C23A—O24A—C12A—C11A	169.7 (2)	N19A—C20A—C21A—C14A	52.6 (4)
C24B—O2B—C2B—C1B	7.4 (5)	N19A—C20A—C21A—C22A	−128.6 (3)
C24B—O2B—C2B—C3B	−174.2 (3)	C14A—C21A—C22A—C23A	−5.2 (5)
C31B—O3B—C3B—C4B	−4.3 (4)	C20A—C21A—C22A—C23A	176.1 (3)
C31B—O3B—C3B—C2B	174.7 (3)	C21A—C22A—C23A—O24A	−61.3 (4)
C23B—O24B—C12B—C11B	167.8 (2)	C2B—C1B—C6B—C7B	−174.7 (3)
C23B—O24B—C12B—C13B	−71.6 (3)	C2B—C1B—C6B—C5B	0.6 (5)
C12B—O24B—C23B—C22B	87.0 (3)	C6B—C1B—C2B—O2B	−177.6 (3)
C5A—N9A—C8A—C13A	−110.1 (2)	C6B—C1B—C2B—C3B	4.1 (5)
C5A—N9A—C8A—C7A	14.5 (3)	O2B—C2B—C3B—O3B	−3.0 (4)
C8A—N9A—C10A—C11A	8.1 (4)	C1B—C2B—C3B—O3B	175.5 (3)
C8A—N9A—C10A—O25A	−172.9 (3)	C1B—C2B—C3B—C4B	−5.4 (5)
C10A—N9A—C5A—C4A	22.5 (5)	O2B—C2B—C3B—C4B	176.1 (3)
C8A—N9A—C5A—C4A	173.9 (3)	O3B—C3B—C4B—C5B	−179.1 (3)
C8A—N9A—C5A—C6A	−4.7 (3)	C2B—C3B—C4B—C5B	1.9 (5)
C5A—N9A—C10A—O25A	−24.2 (5)	C3B—C4B—C5B—C6B	2.9 (5)
C10A—N9A—C5A—C6A	−156.1 (3)	C3B—C4B—C5B—N9B	−176.9 (3)
C5A—N9A—C10A—C11A	156.8 (3)	C4B—C5B—C6B—C7B	171.9 (3)
C10A—N9A—C8A—C13A	43.2 (3)	C4B—C5B—C6B—C1B	−4.3 (5)
C10A—N9A—C8A—C7A	167.8 (3)	N9B—C5B—C6B—C1B	175.6 (3)
C18A—N19A—C16A—C15A	−134.9 (3)	N9B—C5B—C6B—C7B	−8.2 (4)
C20A—N19A—C18A—C17A	−141.9 (3)	C1B—C6B—C7B—C17B	73.2 (4)
C20A—N19A—C16A—C7A	113.7 (3)	C1B—C6B—C7B—C8B	−167.7 (3)
C18A—N19A—C20A—C21A	76.0 (3)	C5B—C6B—C7B—C17B	−102.5 (3)
C16A—N19A—C20A—C21A	−44.4 (4)	C1B—C6B—C7B—C16B	−43.0 (5)
C16A—N19A—C18A—C17A	−17.7 (3)	C5B—C6B—C7B—C16B	141.3 (3)
C18A—N19A—C16A—C7A	−9.4 (3)	C5B—C6B—C7B—C8B	16.6 (3)
C20A—N19A—C16A—C15A	−11.8 (3)	C8B—C7B—C17B—C18B	78.1 (3)
C10B—N9B—C5B—C4B	24.2 (5)	C6B—C7B—C17B—C18B	−167.8 (3)
C8B—N9B—C5B—C6B	−4.5 (3)	C8B—C7B—C16B—C15B	34.2 (4)
C5B—N9B—C8B—C13B	−110.3 (3)	C17B—C7B—C16B—N19B	31.7 (3)
C5B—N9B—C8B—C7B	14.7 (3)	C17B—C7B—C16B—C15B	153.4 (3)
C8B—N9B—C5B—C4B	175.3 (3)	C16B—C7B—C8B—N9B	−144.0 (3)
C10B—N9B—C5B—C6B	−155.6 (3)	C6B—C7B—C8B—N9B	−18.2 (3)
C5B—N9B—C10B—O25B	−23.6 (5)	C6B—C7B—C8B—C13B	99.5 (3)
C10B—N9B—C8B—C7B	167.4 (3)	C17B—C7B—C8B—N9B	102.2 (3)
C8B—N9B—C10B—O25B	−171.9 (3)	C17B—C7B—C8B—C13B	−140.1 (3)
C10B—N9B—C8B—C13B	42.4 (3)	C16B—C7B—C8B—C13B	−26.3 (4)
C8B—N9B—C10B—C11B	8.2 (4)	C6B—C7B—C16B—C15B	−84.3 (4)
C5B—N9B—C10B—C11B	156.5 (3)	C8B—C7B—C16B—N19B	−87.5 (3)
C16B—N19B—C18B—C17B	−18.0 (3)	C6B—C7B—C16B—N19B	154.0 (3)
C16B—N19B—C20B—C21B	−46.3 (3)	C16B—C7B—C17B—C18B	−43.3 (3)
C20B—N19B—C16B—C15B	−10.4 (4)	N9B—C8B—C13B—C14B	157.2 (3)
C20B—N19B—C18B—C17B	−142.6 (3)	N9B—C8B—C13B—C12B	−71.2 (3)
C20B—N19B—C16B—C7B	115.0 (3)	C7B—C8B—C13B—C12B	172.4 (2)
C18B—N19B—C20B—C21B	74.8 (3)	C7B—C8B—C13B—C14B	40.9 (4)
C18B—N19B—C16B—C15B	−134.5 (3)	N9B—C10B—C11B—C12B	−31.8 (4)
C18B—N19B—C16B—C7B	−9.2 (3)	O25B—C10B—C11B—C12B	148.4 (3)
C6A—C1A—C2A—O2A	−178.3 (3)	C10B—C11B—C12B—C13B	1.7 (4)
C2A—C1A—C6A—C7A	−174.2 (3)	C10B—C11B—C12B—O24B	124.9 (3)
C6A—C1A—C2A—C3A	1.4 (5)	C11B—C12B—C13B—C8B	48.1 (3)
C2A—C1A—C6A—C5A	1.4 (5)	O24B—C12B—C13B—C8B	−69.3 (3)
O2A—C2A—C3A—C4A	176.7 (3)	C11B—C12B—C13B—C14B	176.5 (3)
O2A—C2A—C3A—O3A	−2.1 (4)	O24B—C12B—C13B—C14B	59.0 (4)
C1A—C2A—C3A—C4A	−3.0 (5)	C8B—C13B—C14B—C21B	60.4 (4)
C1A—C2A—C3A—O3A	178.2 (3)	C8B—C13B—C14B—C15B	−60.8 (3)
C2A—C3A—C4A—C5A	1.7 (5)	C12B—C13B—C14B—C15B	172.9 (3)
O3A—C3A—C4A—C5A	−179.6 (3)	C12B—C13B—C14B—C21B	−65.8 (4)
C3A—C4A—C5A—N9A	−177.3 (3)	C15B—C14B—C21B—C20B	−2.1 (4)
C3A—C4A—C5A—C6A	1.2 (5)	C21B—C14B—C15B—C16B	−56.2 (3)
N9A—C5A—C6A—C1A	175.9 (3)	C13B—C14B—C15B—C16B	67.9 (3)
C4A—C5A—C6A—C1A	−2.8 (5)	C15B—C14B—C21B—C22B	177.2 (3)
N9A—C5A—C6A—C7A	−7.7 (4)	C13B—C14B—C21B—C22B	57.6 (4)
C4A—C5A—C6A—C7A	173.6 (3)	C13B—C14B—C21B—C20B	−121.7 (3)
C1A—C6A—C7A—C8A	−168.1 (3)	C14B—C15B—C16B—C7B	−56.1 (4)
C1A—C6A—C7A—C17A	71.8 (4)	C14B—C15B—C16B—N19B	62.9 (3)
C5A—C6A—C7A—C8A	16.0 (3)	C7B—C17B—C18B—N19B	38.1 (3)
C5A—C6A—C7A—C16A	140.7 (3)	N19B—C20B—C21B—C22B	−125.5 (3)
C1A—C6A—C7A—C16A	−43.4 (4)	N19B—C20B—C21B—C14B	53.8 (3)
C5A—C6A—C7A—C17A	−104.2 (3)	C14B—C21B—C22B—C23B	−4.9 (5)
C8A—C7A—C17A—C18A	80.4 (3)	C20B—C21B—C22B—C23B	174.3 (3)
C6A—C7A—C16A—C15A	−84.6 (3)	C21B—C22B—C23B—O24B	−60.0 (4)
C17A—C7A—C8A—N9A	101.8 (3)	S1C—C1C—C2C—C3C	−176.5 (3)
C6A—C7A—C16A—N19A	152.8 (2)	C6C—C1C—C2C—C3C	1.3 (5)
C17A—C7A—C8A—C13A	−140.2 (3)	C2C—C1C—C6C—C5C	−1.2 (5)
C8A—C7A—C16A—N19A	−89.6 (3)	S1C—C1C—C6C—C5C	176.7 (2)
C6A—C7A—C17A—C18A	−165.7 (2)	C1C—C2C—C3C—C4C	0.7 (5)
C17A—C7A—C16A—N19A	32.2 (3)	C2C—C3C—C4C—C5C	−2.7 (5)
C17A—C7A—C16A—C15A	154.8 (3)	C2C—C3C—C4C—C41C	178.2 (3)
C16A—C7A—C8A—N9A	−142.3 (2)	C3C—C4C—C5C—C6C	2.9 (5)
C16A—C7A—C8A—C13A	−24.3 (4)	C41C—C4C—C5C—C6C	−178.0 (3)
C6A—C7A—C8A—N9A	−17.8 (3)	C4C—C5C—C6C—C1C	−1.0 (5)
C16A—C7A—C17A—C18A	−43.1 (3)	S1D—C1D—C2D—C3D	178.6 (3)
C6A—C7A—C8A—C13A	100.2 (3)	C6D—C1D—C2D—C3D	0.6 (5)
C8A—C7A—C16A—C15A	33.0 (4)	S1D—C1D—C6D—C5D	−179.0 (3)
C7A—C8A—C13A—C14A	39.6 (3)	C2D—C1D—C6D—C5D	−1.1 (5)
C7A—C8A—C13A—C12A	171.8 (2)	C1D—C2D—C3D—C4D	0.3 (5)
N9A—C8A—C13A—C12A	−70.9 (3)	C2D—C3D—C4D—C5D	−0.7 (5)
N9A—C8A—C13A—C14A	156.9 (2)	C2D—C3D—C4D—C41D	179.9 (3)
O25A—C10A—C11A—C12A	147.2 (3)	C3D—C4D—C5D—C6D	0.2 (5)
N9A—C10A—C11A—C12A	−33.7 (4)	C41D—C4D—C5D—C6D	179.6 (3)
C10A—C11A—C12A—C13A	4.5 (4)	C4D—C5D—C6D—C1D	0.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N19A—H19A···O13Cⁱ	0.86 (3)	1.82 (3)	2.675 (3)	177 (2)
N19B—H19B···O11Dⁱⁱ	0.88 (3)	2.38 (3)	3.012 (3)	129 (2)
N19B—H19B···O12Dⁱⁱ	0.88 (3)	1.94 (3)	2.779 (3)	159 (3)
O1W—H11W···O25Aⁱⁱⁱ	0.95 (5)	2.00 (5)	2.886 (4)	154 (4)
O1W—H12W···O12D	0.84 (4)	2.04 (4)	2.856 (4)	166 (4)
O2W—H21W···O25B	0.92 (5)	1.93 (5)	2.832 (4)	167 (5)
O2W—H22W···O5W^iv	0.81 (4)	2.00 (4)	2.804 (5)	169 (4)
O3W—H31W···O11D	0.90 (4)	1.92 (5)	2.819 (4)	180 (6)
O3W—H32W···O4W	0.81 (4)	2.06 (4)	2.847 (4)	167 (4)
O4W—H41W···O13D^v	1.00 (4)	1.87 (4)	2.862 (4)	176 (3)
O4W—H42W···O12C^vi	0.78 (4)	2.03 (4)	2.814 (5)	175 (4)
O5W—H51W···O3W	0.87 (4)	1.96 (4)	2.824 (4)	173 (4)
O5W—H52W···O11Cⁱ	0.87 (4)	2.04 (5)	2.811 (5)	148 (4)
O6W—H61W···O2W	0.90 (5)	1.85 (4)	2.746 (4)	180 (5)
O6W—H62W···O13C^vii	0.90 (4)	2.11 (4)	3.010 (4)	180 (6)
C1A—H1A···O6W^vi	0.95	2.58	3.524 (4)	172
C1B—H1B···O1Wⁱⁱ	0.95	2.55	3.419 (5)	152
C2C—H2C···O11C	0.95	2.47	2.861 (5)	105
C4A—H4A···O25A	0.95	2.41	2.936 (4)	114
C4B—H4B···O25B	0.95	2.38	2.898 (4)	114
C6D—H6D···O13D	0.95	2.57	2.939 (4)	103
C13A—H13A···O2B	1.00	2.58	3.463 (4)	147
C8B—H13B···O24B	1.00	2.59	3.002 (3)	104
C14A—H14A···O3B	1.00	2.33	3.253 (4)	153
C14B—H14B···O3A^iv	1.00	2.50	3.437 (4)	156
C22B—H22B···O11C^viii	0.95	2.54	3.441 (4)	158
C20B—H39B···O4Wⁱⁱ	0.99	2.51	3.499 (4)	173
C20A—H40A···O11D	0.99	2.52	3.186 (4)	124
C20B—H40B···O11C^viii	0.99	2.57	3.497 (5)	157

Symmetry codes: (i) x−1, y, z−1; (ii) −x+1, y+1/2, −z+1; (iii) −x+1, y−1/2, −z; (iv) x+1, y, z; (v) x, y, z+1; (vi) x−1, y, z; (vii) x, y, z−1; (viii) −x+2, y+1/2, −z+2.

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