Supramolecular structures and physicochemical properties of norfloxacin salts

Seven new molecular salts of norfloxacin (1-ethyl-6-fluoro-4-oxo-7-piperazin-1-yl-1H-quinoline-3-carboxylic acid; abbreviated as NF) with various organic acids (adipic acid, mucic acid, o-OH-benzoic acid, m-OH-benzoic acid, p-OH-benzoic acid, naphthalene-1, 5-disulfonic acid and naphthalene-2-sulfonic acid) were synthesized and their crystal structures were determined by X-ray crystallography. Supramolecular structures and reccurring packing patterns are discussed to understand the influence of non-covalent interactions in determination of the crystal packing and hydrate inclusion. The formation of hydrates was commonly observed among various NF salts, except for the adipate salt which exists as an anhydrous form. The physicochemical properties of salts were fully characterized with a variety of analytical techniques, including powder X-ray diffraction (PXRD), Fourier transform IR (FT-IR), Raman spectroscopy, thermogravimetric analysis (TGA), differential scanning calorimetry (DSC), hot-stage microscopy (HSM) and dynamic vapour sorption (DVS) etc. The synthesized norfloxacin salts were found to have different physicochemical properties, superior solubility and hygroscopicity. Particularly, NF adipate was found to be a desirable candidate for further development.

S1. Experimental

S1.1. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

S2. Results and discussion

Computing details

For all compounds, data collection: Bruker SMART; cell refinement: Bruker SMART; data reduction: Bruker SMART; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).

Figures

(20120152_0m)

Crystal data

C44H56F2N6O14	V = 2255.11 (11) Å^3
Mr = 930.95	Z = 2
Triclinic, P1	F(000) = 984.0
a = 9.4994 (3) Å	Dx = 1.371 Mg m^−3
b = 14.3694 (4) Å	Mo Kα radiation, λ = 0.71073 Å
c = 18.1458 (5) Å	µ = 0.11 mm^−1
α = 103.853 (1)°	T = 100 K
β = 96.528 (1)°	Block, colorless
γ = 106.946 (2)°	0.31 × 0.23 × 0.15 mm

Data collection

CCD area detector diffractometer	5556 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
phi and ω scans	h = −11→11
31371 measured reflections	k = −17→17
7942 independent reflections	l = −20→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 0.99	w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 1.0643P] where P = (Fo^2 + 2Fc^2)/3
7942 reflections	(Δ/σ)max = 0.001
633 parameters	Δρmax = 0.68 e Å^−3
164 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O3Y	0.09506 (16)	0.71691 (11)	0.55069 (8)	0.0386 (4)
O1Y	0.40092 (16)	0.29493 (11)	0.47177 (9)	0.0405 (4)
O4X	0.55392 (17)	0.17700 (11)	0.45828 (9)	0.0400 (4)
H10'	0.495 (3)	0.219 (2)	0.4646 (15)	0.060*
O3X	0.5423 (2)	0.18818 (15)	0.58111 (10)	0.0655 (5)
O1X	0.9071 (2)	−0.18355 (14)	0.68179 (10)	0.0589 (5)
O1A	−0.3670 (2)	0.86399 (16)	1.12710 (11)	0.0738 (6)
O2A	−0.1405 (2)	0.94601 (15)	1.19827 (10)	0.0608 (5)
O3A	0.0877 (2)	0.96134 (14)	1.13573 (9)	0.0566 (5)
F1A	0.41171 (15)	0.91658 (12)	0.93795 (8)	0.0671 (5)
N3A	0.3352 (2)	0.73711 (14)	0.66485 (10)	0.0348 (4)
O2B	1.1294 (3)	0.54982 (18)	−0.15755 (12)	0.0879 (7)
H28	1.0436	0.5345	−0.1495	0.132*
O1B	1.3554 (3)	0.6509 (2)	−0.09273 (14)	0.1025 (8)
O3B	0.9041 (3)	0.53883 (15)	−0.09410 (10)	0.0733 (6)
F1B	0.58306 (16)	0.58257 (12)	0.10412 (8)	0.0650 (4)
N3B	0.7313 (2)	0.69798 (15)	0.39929 (11)	0.0382 (4)
O4Y	−0.03338 (19)	0.63743 (14)	0.43068 (9)	0.0574 (5)
N2A	0.22813 (19)	0.80111 (13)	0.80036 (10)	0.0381 (4)
N1A	−0.1982 (2)	0.80455 (15)	0.92662 (10)	0.0445 (5)
C5A	0.0559 (2)	0.88715 (16)	1.00071 (12)	0.0361 (5)
N2B	0.76965 (19)	0.69207 (13)	0.24427 (10)	0.0367 (4)
C1Y	0.3975 (2)	0.35251 (15)	0.42878 (12)	0.0315 (5)
O2Y	0.47495 (18)	0.36090 (13)	0.37836 (9)	0.0487 (4)
C1X	0.9029 (2)	−0.13542 (16)	0.63617 (13)	0.0375 (5)
C2X	0.8266 (3)	−0.05630 (17)	0.64539 (13)	0.0411 (5)
H3'	0.8842	0.0001	0.6901	0.049*
H2'	0.7286	−0.0852	0.6568	0.049*
C3X	0.8053 (2)	−0.01472 (16)	0.57773 (13)	0.0378 (5)
H5'	0.7516	−0.0707	0.5320	0.045*
H4'	0.9030	0.0189	0.5681	0.045*
C4X	0.7192 (2)	0.06014 (16)	0.59084 (13)	0.0373 (5)
H7'	0.6245	0.0284	0.6043	0.045*
H6'	0.7766	0.1189	0.6339	0.045*
C5X	0.6891 (2)	0.09420 (17)	0.51948 (14)	0.0414 (5)
H9'	0.7844	0.1324	0.5100	0.050*
H8'	0.6440	0.0344	0.4754	0.050*
C6X	0.5890 (2)	0.15817 (15)	0.52413 (13)	0.0357 (5)
C13A	0.2463 (2)	0.66372 (16)	0.70165 (12)	0.0359 (5)
H17	0.3131	0.6505	0.7393	0.043*
H16	0.1908	0.6000	0.6626	0.043*
C14A	0.1389 (2)	0.70741 (16)	0.74096 (12)	0.0348 (5)
H18	0.0722	0.7213	0.7037	0.042*
H19	0.0786	0.6597	0.7642	0.042*
C8A	0.1659 (2)	0.83386 (16)	0.86427 (12)	0.0365 (5)
C9A	0.0135 (2)	0.80628 (17)	0.86212 (12)	0.0385 (5)
H3	−0.0528	0.7701	0.8153	0.046*
C10A	−0.0433 (2)	0.83194 (16)	0.92947 (12)	0.0367 (5)
C1A	−0.2492 (3)	0.82580 (19)	0.99254 (13)	0.0468 (6)
H1	−0.3525	0.8054	0.9894	0.056*
C2A	−0.1595 (3)	0.87527 (17)	1.06383 (13)	0.0409 (5)
C3A	−0.2331 (3)	0.89331 (19)	1.13152 (14)	0.0491 (6)
C15A	−0.3073 (3)	0.7540 (2)	0.85188 (14)	0.0598 (7)
H5	−0.2676	0.7827	0.8123	0.072*
H4	−0.4003	0.7678	0.8571	0.072*
C16A	−0.3395 (3)	0.6422 (2)	0.82674 (17)	0.0749 (9)
H8	−0.2470	0.6280	0.8253	0.112*
H7	−0.4023	0.6140	0.7761	0.112*
H6	−0.3900	0.6124	0.8626	0.112*
C4A	−0.0005 (3)	0.91138 (16)	1.07162 (12)	0.0392 (5)
C6A	0.2109 (3)	0.91721 (17)	1.00194 (13)	0.0426 (5)
H2	0.2784	0.9549	1.0481	0.051*
C7A	0.2621 (2)	0.89129 (17)	0.93584 (13)	0.0422 (5)
C11A	0.3110 (2)	0.87789 (16)	0.76618 (13)	0.0407 (5)
H10	0.3678	0.9398	0.8068	0.049*
H11	0.2412	0.8935	0.7317	0.049*
C12A	0.4164 (2)	0.83817 (17)	0.72167 (13)	0.0416 (5)
H13	0.4630	0.8858	0.6945	0.050*
H12	0.4952	0.8324	0.7575	0.050*
C13B	0.7843 (3)	0.79221 (17)	0.37611 (13)	0.0430 (5)
H36	0.8504	0.8468	0.4199	0.052*
H35	0.6994	0.8119	0.3595	0.052*
C14B	0.8677 (2)	0.77425 (17)	0.31048 (12)	0.0401 (5)
H37	0.9027	0.8359	0.2951	0.048*
H38	0.9546	0.7569	0.3279	0.048*
C8B	0.8290 (2)	0.67663 (16)	0.17582 (12)	0.0362 (5)
C7B	0.7320 (3)	0.61764 (18)	0.10489 (13)	0.0441 (5)
C6B	0.7821 (3)	0.59406 (18)	0.03778 (13)	0.0486 (6)
H21	0.7142	0.5538	−0.0077	0.058*
C5B	0.9356 (3)	0.63027 (17)	0.03707 (13)	0.0443 (5)
C4B	0.9926 (3)	0.59992 (19)	−0.03296 (14)	0.0538 (6)
C2B	1.1498 (4)	0.6410 (2)	−0.02720 (15)	0.0581 (7)
C3B	1.2223 (5)	0.6152 (3)	−0.09452 (19)	0.0739 (9)
C11B	0.7143 (3)	0.59792 (17)	0.26671 (13)	0.0420 (5)
H30	0.7983	0.5767	0.2822	0.050*
H29	0.6472	0.5445	0.2226	0.050*
C12B	0.6321 (2)	0.61347 (18)	0.33270 (13)	0.0436 (5)
H31	0.5430	0.6289	0.3160	0.052*
H32	0.6007	0.5517	0.3482	0.052*
C9B	0.9790 (2)	0.71591 (17)	0.17440 (13)	0.0395 (5)
H22	1.0455	0.7583	0.2198	0.047*
C10B	1.0339 (3)	0.69334 (17)	0.10583 (13)	0.0423 (5)
N1B	1.1872 (2)	0.73114 (17)	0.10611 (12)	0.0537 (5)
C1B	1.2380 (3)	0.7033 (2)	0.04093 (16)	0.0611 (7)
H20	1.3407	0.7287	0.0428	0.073*
C15B	1.2969 (3)	0.7930 (3)	0.17795 (19)	0.0781 (9)
C16B	1.3397 (5)	0.7303 (4)	0.2236 (2)	0.1274 (17)
H25	1.2511	0.6864	0.2338	0.191*
H27	1.4044	0.7735	0.2717	0.191*
H26	1.3914	0.6901	0.1951	0.191*
C6Y	0.0700 (2)	0.65237 (15)	0.48522 (12)	0.0325 (5)
C5Y	0.1726 (2)	0.58944 (16)	0.47490 (13)	0.0381 (5)
H18'	0.2755	0.6353	0.4899	0.046*
H17'	0.1587	0.5484	0.5105	0.046*
C4Y	0.1533 (3)	0.5205 (2)	0.39554 (13)	0.0502 (6)
H16'	0.1510	0.5587	0.3582	0.060*
H15'	0.0574	0.4666	0.3836	0.060*
C3Y	0.2769 (3)	0.4734 (2)	0.38662 (14)	0.0495 (6)
H13'	0.2566	0.4296	0.3341	0.059*
H14'	0.3717	0.5271	0.3943	0.059*
C2Y	0.2920 (2)	0.41288 (16)	0.44189 (13)	0.0363 (5)
H11'	0.1932	0.3663	0.4395	0.044*
H12'	0.3256	0.4590	0.4939	0.044*
H14	0.404 (2)	0.7100 (18)	0.6451 (14)	0.057 (7)*
H33	0.683 (2)	0.7060 (17)	0.4396 (11)	0.047 (7)*
H15	0.270 (2)	0.7407 (17)	0.6252 (11)	0.050 (7)*
H23	1.267 (3)	0.856 (2)	0.2092 (19)	0.089 (10)*
H9	−0.048 (4)	0.961 (3)	1.186 (2)	0.102 (13)*
O2X	0.96215 (19)	−0.14786 (13)	0.57354 (10)	0.0499 (4)
H24	1.383 (4)	0.843 (3)	0.161 (2)	0.106 (11)*
H34	0.811 (2)	0.6789 (18)	0.4155 (14)	0.058 (7)*
H1'	1.006 (3)	−0.201 (2)	0.5678 (18)	0.086 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O3Y	0.0398 (8)	0.0422 (8)	0.0398 (8)	0.0243 (7)	0.0104 (7)	0.0083 (7)
O1Y	0.0471 (9)	0.0490 (9)	0.0448 (9)	0.0315 (7)	0.0214 (7)	0.0235 (8)
O4X	0.0442 (9)	0.0461 (9)	0.0451 (9)	0.0275 (7)	0.0179 (7)	0.0211 (7)
O3X	0.0963 (14)	0.0898 (14)	0.0465 (10)	0.0696 (12)	0.0314 (10)	0.0292 (10)
O1X	0.0848 (13)	0.0687 (12)	0.0478 (10)	0.0512 (10)	0.0165 (9)	0.0278 (9)
O1A	0.0676 (12)	0.0929 (15)	0.0615 (12)	0.0251 (11)	0.0404 (10)	0.0122 (11)
O2A	0.0787 (13)	0.0746 (13)	0.0375 (10)	0.0355 (11)	0.0274 (10)	0.0112 (9)
O3A	0.0649 (11)	0.0677 (11)	0.0320 (9)	0.0231 (9)	0.0137 (8)	0.0015 (8)
F1A	0.0380 (7)	0.0846 (11)	0.0528 (9)	0.0027 (7)	0.0143 (7)	−0.0083 (8)
N3A	0.0361 (10)	0.0476 (11)	0.0316 (10)	0.0252 (8)	0.0144 (8)	0.0138 (8)
O2B	0.168 (2)	0.0890 (16)	0.0523 (12)	0.0826 (16)	0.0615 (14)	0.0359 (11)
O1B	0.134 (2)	0.134 (2)	0.0920 (17)	0.0791 (17)	0.0860 (16)	0.0548 (16)
O3B	0.1195 (17)	0.0771 (13)	0.0344 (10)	0.0504 (12)	0.0222 (11)	0.0108 (9)
F1B	0.0489 (8)	0.0864 (11)	0.0452 (8)	0.0089 (8)	0.0041 (7)	0.0111 (8)
N3B	0.0390 (10)	0.0569 (12)	0.0326 (10)	0.0266 (9)	0.0179 (9)	0.0197 (9)
O4Y	0.0564 (10)	0.0862 (13)	0.0416 (9)	0.0512 (10)	0.0032 (8)	0.0090 (9)
N2A	0.0417 (10)	0.0391 (10)	0.0329 (10)	0.0117 (8)	0.0181 (8)	0.0062 (8)
N1A	0.0407 (10)	0.0651 (13)	0.0324 (10)	0.0230 (9)	0.0135 (8)	0.0129 (9)
C5A	0.0462 (12)	0.0357 (11)	0.0316 (11)	0.0174 (9)	0.0146 (9)	0.0111 (9)
N2B	0.0409 (10)	0.0400 (10)	0.0293 (9)	0.0112 (8)	0.0119 (8)	0.0108 (8)
C1Y	0.0311 (10)	0.0328 (11)	0.0347 (11)	0.0161 (9)	0.0106 (9)	0.0082 (9)
O2Y	0.0560 (10)	0.0672 (11)	0.0537 (10)	0.0440 (9)	0.0362 (8)	0.0325 (9)
C1X	0.0367 (12)	0.0401 (12)	0.0377 (12)	0.0178 (10)	0.0030 (10)	0.0105 (10)
C2X	0.0469 (13)	0.0443 (13)	0.0377 (12)	0.0250 (11)	0.0067 (10)	0.0105 (10)
C3X	0.0346 (11)	0.0386 (12)	0.0452 (13)	0.0179 (9)	0.0091 (10)	0.0137 (10)
C4X	0.0371 (11)	0.0360 (11)	0.0414 (12)	0.0175 (9)	0.0064 (10)	0.0097 (10)
C5X	0.0430 (12)	0.0432 (13)	0.0528 (14)	0.0243 (10)	0.0194 (11)	0.0234 (11)
C6X	0.0386 (12)	0.0340 (11)	0.0419 (12)	0.0160 (9)	0.0141 (10)	0.0163 (10)
C13A	0.0412 (12)	0.0393 (12)	0.0341 (11)	0.0202 (10)	0.0121 (10)	0.0122 (9)
C14A	0.0367 (11)	0.0385 (11)	0.0321 (11)	0.0150 (9)	0.0124 (9)	0.0097 (9)
C8A	0.0437 (12)	0.0377 (12)	0.0316 (11)	0.0152 (10)	0.0157 (9)	0.0102 (9)
C9A	0.0408 (11)	0.0486 (13)	0.0283 (11)	0.0175 (10)	0.0104 (9)	0.0098 (10)
C10A	0.0397 (11)	0.0451 (12)	0.0320 (11)	0.0193 (10)	0.0139 (9)	0.0138 (10)
C1A	0.0467 (13)	0.0605 (15)	0.0437 (13)	0.0257 (12)	0.0229 (11)	0.0176 (12)
C2A	0.0549 (13)	0.0445 (13)	0.0351 (11)	0.0259 (11)	0.0210 (10)	0.0156 (10)
C3A	0.0654 (16)	0.0524 (15)	0.0434 (14)	0.0296 (13)	0.0290 (12)	0.0179 (12)
C15A	0.0427 (13)	0.099 (2)	0.0430 (14)	0.0317 (14)	0.0127 (11)	0.0186 (14)
C16A	0.0550 (17)	0.098 (2)	0.0539 (17)	0.0156 (16)	0.0081 (14)	0.0023 (16)
C4A	0.0553 (13)	0.0391 (12)	0.0317 (11)	0.0234 (10)	0.0161 (10)	0.0122 (10)
C6A	0.0460 (12)	0.0427 (13)	0.0319 (12)	0.0111 (10)	0.0082 (10)	0.0020 (10)
C7A	0.0362 (11)	0.0450 (13)	0.0404 (12)	0.0103 (10)	0.0138 (10)	0.0040 (10)
C11A	0.0447 (13)	0.0387 (12)	0.0413 (13)	0.0135 (10)	0.0206 (10)	0.0109 (10)
C12A	0.0381 (12)	0.0486 (13)	0.0390 (12)	0.0139 (10)	0.0150 (10)	0.0115 (10)
C13B	0.0487 (13)	0.0466 (13)	0.0380 (12)	0.0192 (11)	0.0166 (11)	0.0118 (10)
C14B	0.0439 (12)	0.0412 (12)	0.0344 (12)	0.0107 (10)	0.0153 (10)	0.0100 (10)
C8B	0.0462 (12)	0.0395 (12)	0.0291 (10)	0.0182 (10)	0.0139 (9)	0.0130 (9)
C7B	0.0464 (13)	0.0494 (14)	0.0360 (12)	0.0139 (11)	0.0081 (10)	0.0139 (11)
C6B	0.0698 (15)	0.0480 (14)	0.0281 (11)	0.0206 (12)	0.0076 (11)	0.0106 (10)
C5B	0.0694 (15)	0.0468 (13)	0.0316 (11)	0.0316 (12)	0.0205 (11)	0.0184 (10)
C4B	0.1001 (18)	0.0531 (15)	0.0330 (13)	0.0476 (14)	0.0274 (13)	0.0232 (11)
C2B	0.0940 (18)	0.0654 (17)	0.0479 (14)	0.0512 (15)	0.0435 (14)	0.0321 (13)
C3B	0.131 (3)	0.081 (2)	0.0607 (18)	0.074 (2)	0.0608 (19)	0.0461 (16)
C11B	0.0470 (13)	0.0407 (12)	0.0365 (12)	0.0089 (10)	0.0135 (10)	0.0122 (10)
C12B	0.0375 (12)	0.0525 (14)	0.0434 (13)	0.0111 (10)	0.0146 (10)	0.0201 (11)
C9B	0.0453 (12)	0.0443 (13)	0.0308 (11)	0.0155 (10)	0.0142 (10)	0.0103 (10)
C10B	0.0536 (13)	0.0470 (13)	0.0385 (12)	0.0245 (11)	0.0212 (10)	0.0190 (10)
N1B	0.0564 (12)	0.0713 (14)	0.0447 (11)	0.0272 (11)	0.0292 (10)	0.0207 (10)
C1B	0.0771 (18)	0.0778 (19)	0.0566 (15)	0.0426 (15)	0.0435 (14)	0.0352 (14)
C15B	0.0486 (16)	0.119 (3)	0.0584 (18)	0.0184 (17)	0.0240 (14)	0.0148 (18)
C16B	0.116 (3)	0.226 (5)	0.065 (2)	0.105 (4)	0.009 (2)	0.033 (3)
C6Y	0.0308 (10)	0.0377 (11)	0.0381 (12)	0.0175 (9)	0.0135 (9)	0.0165 (10)
C5Y	0.0325 (11)	0.0362 (12)	0.0463 (13)	0.0185 (9)	0.0055 (10)	0.0057 (10)
C4Y	0.0651 (16)	0.0664 (16)	0.0365 (12)	0.0480 (14)	0.0117 (12)	0.0130 (12)
C3Y	0.0675 (16)	0.0664 (16)	0.0427 (13)	0.0496 (14)	0.0272 (12)	0.0251 (12)
C2Y	0.0365 (11)	0.0385 (12)	0.0438 (12)	0.0215 (9)	0.0188 (10)	0.0137 (10)
O2X	0.0578 (10)	0.0560 (10)	0.0596 (11)	0.0396 (9)	0.0257 (9)	0.0278 (9)

Geometric parameters (Å, º)

O3Y—C6Y	1.268 (2)	C1A—C2A	1.364 (3)
O1Y—C1Y	1.270 (2)	C1A—H1	0.9300
O4X—C6X	1.315 (3)	C2A—C4A	1.425 (3)
O4X—H10'	0.93 (3)	C2A—C3A	1.487 (3)
O3X—C6X	1.206 (3)	C15A—C16A	1.488 (4)
O1X—C1X	1.203 (3)	C15A—H5	0.9700
O1A—C3A	1.204 (3)	C15A—H4	0.9700
O2A—C3A	1.321 (3)	C16A—H8	0.9600
O2A—H9	0.91 (4)	C16A—H7	0.9600
O3A—C4A	1.264 (3)	C16A—H6	0.9600
F1A—C7A	1.354 (2)	C6A—C7A	1.356 (3)
N3A—C12A	1.489 (3)	C6A—H2	0.9300
N3A—C13A	1.489 (3)	C11A—C12A	1.509 (3)
N3A—H14	0.918 (17)	C11A—H10	0.9700
N3A—H15	0.914 (16)	C11A—H11	0.9700
O2B—C3B	1.320 (4)	C12A—H13	0.9700
O2B—H28	0.8200	C12A—H12	0.9700
O1B—C3B	1.211 (4)	C13B—C14B	1.516 (3)
O3B—C4B	1.265 (3)	C13B—H36	0.9700
F1B—C7B	1.354 (3)	C13B—H35	0.9700
N3B—C13B	1.479 (3)	C14B—H37	0.9700
N3B—C12B	1.481 (3)	C14B—H38	0.9700
N3B—H33	0.906 (16)	C8B—C9B	1.377 (3)
N3B—H34	0.917 (16)	C8B—C7B	1.406 (3)
O4Y—C6Y	1.243 (2)	C7B—C6B	1.361 (3)
N2A—C8A	1.404 (3)	C6B—C5B	1.401 (3)
N2A—C14A	1.458 (3)	C6B—H21	0.9300
N2A—C11A	1.468 (3)	C5B—C10B	1.396 (3)
N1A—C1A	1.342 (3)	C5B—C4B	1.459 (3)
N1A—C10A	1.400 (3)	C4B—C2B	1.417 (4)
N1A—C15A	1.487 (3)	C2B—C1B	1.353 (4)
C5A—C6A	1.404 (3)	C2B—C3B	1.492 (4)
C5A—C10A	1.409 (3)	C11B—C12B	1.510 (3)
C5A—C4A	1.455 (3)	C11B—H30	0.9700
N2B—C8B	1.418 (3)	C11B—H29	0.9700
N2B—C14B	1.460 (3)	C12B—H31	0.9700
N2B—C11B	1.473 (3)	C12B—H32	0.9700
C1Y—O2Y	1.243 (2)	C9B—C10B	1.406 (3)
C1Y—C2Y	1.509 (3)	C9B—H22	0.9300
C1X—O2X	1.322 (3)	C10B—N1B	1.397 (3)
C1X—C2X	1.505 (3)	N1B—C1B	1.345 (3)
C2X—C3X	1.507 (3)	N1B—C15B	1.474 (4)
C2X—H3'	0.9700	C1B—H20	0.9300
C2X—H2'	0.9700	C15B—C16B	1.468 (5)
C3X—C4X	1.522 (3)	C15B—H23	1.08 (3)
C3X—H5'	0.9700	C15B—H24	1.06 (4)
C3X—H4'	0.9700	C16B—H25	0.9600
C4X—C5X	1.516 (3)	C16B—H27	0.9600
C4X—H7'	0.9700	C16B—H26	0.9600
C4X—H6'	0.9700	C6Y—C5Y	1.509 (3)
C5X—C6X	1.500 (3)	C5Y—C4Y	1.496 (3)
C5X—H9'	0.9700	C5Y—H18'	0.9700
C5X—H8'	0.9700	C5Y—H17'	0.9700
C13A—C14A	1.506 (3)	C4Y—C3Y	1.522 (3)
C13A—H17	0.9700	C4Y—H16'	0.9700
C13A—H16	0.9700	C4Y—H15'	0.9700
C14A—H18	0.9700	C3Y—C2Y	1.497 (3)
C14A—H19	0.9700	C3Y—H13'	0.9700
C8A—C9A	1.378 (3)	C3Y—H14'	0.9700
C8A—C7A	1.407 (3)	C2Y—H11'	0.9700
C9A—C10A	1.404 (3)	C2Y—H12'	0.9700
C9A—H3	0.9300	O2X—H1'	0.96 (3)
C6X—O4X—H10'	109.5 (16)	C6A—C7A—C8A	122.8 (2)
C3A—O2A—H9	104 (2)	N2A—C11A—C12A	109.53 (18)
C12A—N3A—C13A	112.03 (16)	N2A—C11A—H10	109.8
C12A—N3A—H14	108.9 (16)	C12A—C11A—H10	109.8
C13A—N3A—H14	106.5 (16)	N2A—C11A—H11	109.8
C12A—N3A—H15	112.5 (15)	C12A—C11A—H11	109.8
C13A—N3A—H15	107.2 (15)	H10—C11A—H11	108.2
H14—N3A—H15	109 (2)	N3A—C12A—C11A	111.11 (17)
C3B—O2B—H28	109.5	N3A—C12A—H13	109.4
C13B—N3B—C12B	110.49 (17)	C11A—C12A—H13	109.4
C13B—N3B—H33	112.2 (15)	N3A—C12A—H12	109.4
C12B—N3B—H33	110.1 (15)	C11A—C12A—H12	109.4
C13B—N3B—H34	110.6 (16)	H13—C12A—H12	108.0
C12B—N3B—H34	107.2 (16)	N3B—C13B—C14B	109.31 (18)
H33—N3B—H34	106 (2)	N3B—C13B—H36	109.8
C8A—N2A—C14A	118.07 (17)	C14B—C13B—H36	109.8
C8A—N2A—C11A	117.93 (17)	N3B—C13B—H35	109.8
C14A—N2A—C11A	111.41 (16)	C14B—C13B—H35	109.8
C1A—N1A—C10A	119.31 (19)	H36—C13B—H35	108.3
C1A—N1A—C15A	119.40 (19)	N2B—C14B—C13B	110.39 (18)
C10A—N1A—C15A	121.29 (18)	N2B—C14B—H37	109.6
C6A—C5A—C10A	118.47 (19)	C13B—C14B—H37	109.6
C6A—C5A—C4A	120.7 (2)	N2B—C14B—H38	109.6
C10A—C5A—C4A	120.9 (2)	C13B—C14B—H38	109.6
C8B—N2B—C14B	115.58 (17)	H37—C14B—H38	108.1
C8B—N2B—C11B	112.37 (17)	C9B—C8B—C7B	117.02 (19)
C14B—N2B—C11B	110.34 (16)	C9B—C8B—N2B	123.54 (19)
O2Y—C1Y—O1Y	123.83 (18)	C7B—C8B—N2B	119.44 (19)
O2Y—C1Y—C2Y	120.14 (18)	F1B—C7B—C6B	119.2 (2)
O1Y—C1Y—C2Y	116.03 (17)	F1B—C7B—C8B	118.1 (2)
O1X—C1X—O2X	123.6 (2)	C6B—C7B—C8B	122.7 (2)
O1X—C1X—C2X	122.2 (2)	C7B—C6B—C5B	120.2 (2)
O2X—C1X—C2X	114.16 (19)	C7B—C6B—H21	119.9
C1X—C2X—C3X	116.91 (19)	C5B—C6B—H21	119.9
C1X—C2X—H3'	108.1	C10B—C5B—C6B	118.4 (2)
C3X—C2X—H3'	108.1	C10B—C5B—C4B	120.5 (2)
C1X—C2X—H2'	108.1	C6B—C5B—C4B	121.0 (2)
C3X—C2X—H2'	108.1	O3B—C4B—C2B	123.3 (2)
H3'—C2X—H2'	107.3	O3B—C4B—C5B	120.4 (3)
C2X—C3X—C4X	112.96 (18)	C2B—C4B—C5B	116.3 (2)
C2X—C3X—H5'	109.0	C1B—C2B—C4B	120.0 (2)
C4X—C3X—H5'	109.0	C1B—C2B—C3B	118.5 (3)
C2X—C3X—H4'	109.0	C4B—C2B—C3B	121.5 (3)
C4X—C3X—H4'	109.0	O1B—C3B—O2B	121.7 (3)
H5'—C3X—H4'	107.8	O1B—C3B—C2B	123.6 (3)
C5X—C4X—C3X	111.64 (18)	O2B—C3B—C2B	114.6 (3)
C5X—C4X—H7'	109.3	N2B—C11B—C12B	110.97 (18)
C3X—C4X—H7'	109.3	N2B—C11B—H30	109.4
C5X—C4X—H6'	109.3	C12B—C11B—H30	109.4
C3X—C4X—H6'	109.3	N2B—C11B—H29	109.4
H7'—C4X—H6'	108.0	C12B—C11B—H29	109.4
C6X—C5X—C4X	115.04 (18)	H30—C11B—H29	108.0
C6X—C5X—H9'	108.5	N3B—C12B—C11B	109.94 (17)
C4X—C5X—H9'	108.5	N3B—C12B—H31	109.7
C6X—C5X—H8'	108.5	C11B—C12B—H31	109.7
C4X—C5X—H8'	108.5	N3B—C12B—H32	109.7
H9'—C5X—H8'	107.5	C11B—C12B—H32	109.7
O3X—C6X—O4X	122.82 (19)	H31—C12B—H32	108.2
O3X—C6X—C5X	124.5 (2)	C8B—C9B—C10B	121.4 (2)
O4X—C6X—C5X	112.68 (19)	C8B—C9B—H22	119.3
N3A—C13A—C14A	109.33 (17)	C10B—C9B—H22	119.3
N3A—C13A—H17	109.8	C5B—C10B—N1B	119.3 (2)
C14A—C13A—H17	109.8	C5B—C10B—C9B	120.1 (2)
N3A—C13A—H16	109.8	N1B—C10B—C9B	120.6 (2)
C14A—C13A—H16	109.8	C1B—N1B—C10B	119.4 (2)
H17—C13A—H16	108.3	C1B—N1B—C15B	118.7 (2)
N2A—C14A—C13A	107.46 (17)	C10B—N1B—C15B	121.6 (2)
N2A—C14A—H18	110.2	N1B—C1B—C2B	124.4 (3)
C13A—C14A—H18	110.2	N1B—C1B—H20	117.8
N2A—C14A—H19	110.2	C2B—C1B—H20	117.8
C13A—C14A—H19	110.2	C16B—C15B—N1B	112.2 (3)
H18—C14A—H19	108.5	C16B—C15B—H23	116.3 (17)
C9A—C8A—N2A	123.10 (19)	N1B—C15B—H23	112.9 (17)
C9A—C8A—C7A	117.59 (19)	C16B—C15B—H24	117.6 (19)
N2A—C8A—C7A	119.13 (19)	N1B—C15B—H24	105.4 (19)
C8A—C9A—C10A	121.1 (2)	H23—C15B—H24	90 (2)
C8A—C9A—H3	119.5	C15B—C16B—H25	109.5
C10A—C9A—H3	119.5	C15B—C16B—H27	109.5
N1A—C10A—C9A	120.71 (19)	H25—C16B—H27	109.5
N1A—C10A—C5A	119.27 (18)	C15B—C16B—H26	109.5
C9A—C10A—C5A	120.02 (19)	H25—C16B—H26	109.5
N1A—C1A—C2A	124.4 (2)	H27—C16B—H26	109.5
N1A—C1A—H1	117.8	O4Y—C6Y—O3Y	124.31 (18)
C2A—C1A—H1	117.8	O4Y—C6Y—C5Y	119.05 (19)
C1A—C2A—C4A	120.1 (2)	O3Y—C6Y—C5Y	116.63 (18)
C1A—C2A—C3A	118.0 (2)	C4Y—C5Y—C6Y	116.81 (18)
C4A—C2A—C3A	121.8 (2)	C4Y—C5Y—H18'	108.1
O1A—C3A—O2A	121.3 (2)	C6Y—C5Y—H18'	108.1
O1A—C3A—C2A	123.6 (2)	C4Y—C5Y—H17'	108.1
O2A—C3A—C2A	115.1 (2)	C6Y—C5Y—H17'	108.1
N1A—C15A—C16A	112.6 (2)	H18'—C5Y—H17'	107.3
N1A—C15A—H5	109.1	C5Y—C4Y—C3Y	113.47 (19)
C16A—C15A—H5	109.1	C5Y—C4Y—H16'	108.9
N1A—C15A—H4	109.1	C3Y—C4Y—H16'	108.9
C16A—C15A—H4	109.1	C5Y—C4Y—H15'	108.9
H5—C15A—H4	107.8	C3Y—C4Y—H15'	108.9
C15A—C16A—H8	109.5	H16'—C4Y—H15'	107.7
C15A—C16A—H7	109.5	C2Y—C3Y—C4Y	113.76 (19)
H8—C16A—H7	109.5	C2Y—C3Y—H13'	108.8
C15A—C16A—H6	109.5	C4Y—C3Y—H13'	108.8
H8—C16A—H6	109.5	C2Y—C3Y—H14'	108.8
H7—C16A—H6	109.5	C4Y—C3Y—H14'	108.8
O3A—C4A—C2A	122.9 (2)	H13'—C3Y—H14'	107.7
O3A—C4A—C5A	121.3 (2)	C3Y—C2Y—C1Y	116.22 (17)
C2A—C4A—C5A	115.8 (2)	C3Y—C2Y—H11'	108.2
C7A—C6A—C5A	120.0 (2)	C1Y—C2Y—H11'	108.2
C7A—C6A—H2	120.0	C3Y—C2Y—H12'	108.2
C5A—C6A—H2	120.0	C1Y—C2Y—H12'	108.2
F1A—C7A—C6A	119.8 (2)	H11'—C2Y—H12'	107.4
F1A—C7A—C8A	117.36 (18)	C1X—O2X—H1'	112.4 (18)
O1X—C1X—C2X—C3X	−169.5 (2)	C12B—N3B—C13B—C14B	−58.6 (2)
O2X—C1X—C2X—C3X	9.5 (3)	C8B—N2B—C14B—C13B	172.39 (18)
C1X—C2X—C3X—C4X	176.68 (19)	C11B—N2B—C14B—C13B	−58.8 (2)
C2X—C3X—C4X—C5X	−175.54 (19)	N3B—C13B—C14B—N2B	59.3 (2)
C3X—C4X—C5X—C6X	172.96 (19)	C14B—N2B—C8B—C9B	16.1 (3)
C4X—C5X—C6X—O3X	5.3 (3)	C11B—N2B—C8B—C9B	−111.7 (2)
C4X—C5X—C6X—O4X	−173.46 (18)	C14B—N2B—C8B—C7B	−164.4 (2)
C12A—N3A—C13A—C14A	56.5 (2)	C11B—N2B—C8B—C7B	67.7 (3)
C8A—N2A—C14A—C13A	−154.21 (18)	C9B—C8B—C7B—F1B	−176.6 (2)
C11A—N2A—C14A—C13A	64.6 (2)	N2B—C8B—C7B—F1B	3.9 (3)
N3A—C13A—C14A—N2A	−61.1 (2)	C9B—C8B—C7B—C6B	3.9 (3)
C14A—N2A—C8A—C9A	−24.0 (3)	N2B—C8B—C7B—C6B	−175.6 (2)
C11A—N2A—C8A—C9A	114.7 (2)	F1B—C7B—C6B—C5B	179.4 (2)
C14A—N2A—C8A—C7A	151.1 (2)	C8B—C7B—C6B—C5B	−1.1 (4)
C11A—N2A—C8A—C7A	−70.2 (3)	C7B—C6B—C5B—C10B	−2.1 (3)
N2A—C8A—C9A—C10A	173.2 (2)	C7B—C6B—C5B—C4B	175.6 (2)
C7A—C8A—C9A—C10A	−1.9 (3)	C10B—C5B—C4B—O3B	176.5 (2)
C1A—N1A—C10A—C9A	176.8 (2)	C6B—C5B—C4B—O3B	−1.1 (3)
C15A—N1A—C10A—C9A	−4.3 (3)	C10B—C5B—C4B—C2B	−2.3 (3)
C1A—N1A—C10A—C5A	−4.2 (3)	C6B—C5B—C4B—C2B	−179.9 (2)
C15A—N1A—C10A—C5A	174.7 (2)	O3B—C4B—C2B—C1B	−177.9 (2)
C8A—C9A—C10A—N1A	179.3 (2)	C5B—C4B—C2B—C1B	0.9 (3)
C8A—C9A—C10A—C5A	0.3 (3)	O3B—C4B—C2B—C3B	0.8 (4)
C6A—C5A—C10A—N1A	−177.7 (2)	C5B—C4B—C2B—C3B	179.5 (2)
C4A—C5A—C10A—N1A	3.1 (3)	C1B—C2B—C3B—O1B	−3.6 (4)
C6A—C5A—C10A—C9A	1.4 (3)	C4B—C2B—C3B—O1B	177.8 (3)
C4A—C5A—C10A—C9A	−177.8 (2)	C1B—C2B—C3B—O2B	176.6 (2)
C10A—N1A—C1A—C2A	1.5 (4)	C4B—C2B—C3B—O2B	−2.0 (4)
C15A—N1A—C1A—C2A	−177.4 (2)	C8B—N2B—C11B—C12B	−171.82 (18)
N1A—C1A—C2A—C4A	2.2 (4)	C14B—N2B—C11B—C12B	57.6 (2)
N1A—C1A—C2A—C3A	179.9 (2)	C13B—N3B—C12B—C11B	57.5 (2)
C1A—C2A—C3A—O1A	2.3 (4)	N2B—C11B—C12B—N3B	−56.6 (2)
C4A—C2A—C3A—O1A	180.0 (2)	C7B—C8B—C9B—C10B	−3.4 (3)
C1A—C2A—C3A—O2A	−176.7 (2)	N2B—C8B—C9B—C10B	176.0 (2)
C4A—C2A—C3A—O2A	0.9 (3)	C6B—C5B—C10B—N1B	−179.3 (2)
C1A—N1A—C15A—C16A	−97.2 (3)	C4B—C5B—C10B—N1B	3.0 (3)
C10A—N1A—C15A—C16A	83.9 (3)	C6B—C5B—C10B—C9B	2.5 (3)
C1A—C2A—C4A—O3A	177.0 (2)	C4B—C5B—C10B—C9B	−175.2 (2)
C3A—C2A—C4A—O3A	−0.6 (3)	C8B—C9B—C10B—C5B	0.3 (3)
C1A—C2A—C4A—C5A	−3.1 (3)	C8B—C9B—C10B—N1B	−177.8 (2)
C3A—C2A—C4A—C5A	179.3 (2)	C5B—C10B—N1B—C1B	−2.3 (3)
C6A—C5A—C4A—O3A	1.2 (3)	C9B—C10B—N1B—C1B	175.9 (2)
C10A—C5A—C4A—O3A	−179.6 (2)	C5B—C10B—N1B—C15B	−176.3 (3)
C6A—C5A—C4A—C2A	−178.7 (2)	C9B—C10B—N1B—C15B	1.8 (4)
C10A—C5A—C4A—C2A	0.5 (3)	C10B—N1B—C1B—C2B	1.0 (4)
C10A—C5A—C6A—C7A	−1.3 (3)	C15B—N1B—C1B—C2B	175.2 (3)
C4A—C5A—C6A—C7A	177.9 (2)	C4B—C2B—C1B—N1B	−0.3 (4)
C5A—C6A—C7A—F1A	−177.1 (2)	C3B—C2B—C1B—N1B	−178.9 (2)
C5A—C6A—C7A—C8A	−0.4 (4)	C1B—N1B—C15B—C16B	−92.1 (3)
C9A—C8A—C7A—F1A	178.8 (2)	C10B—N1B—C15B—C16B	82.0 (3)
N2A—C8A—C7A—F1A	3.5 (3)	O4Y—C6Y—C5Y—C4Y	6.8 (3)
C9A—C8A—C7A—C6A	2.0 (3)	O3Y—C6Y—C5Y—C4Y	−174.2 (2)
N2A—C8A—C7A—C6A	−173.3 (2)	C6Y—C5Y—C4Y—C3Y	170.3 (2)
C8A—N2A—C11A—C12A	158.14 (19)	C5Y—C4Y—C3Y—C2Y	58.2 (3)
C14A—N2A—C11A—C12A	−60.6 (2)	C4Y—C3Y—C2Y—C1Y	171.8 (2)
C13A—N3A—C12A—C11A	−52.4 (2)	O2Y—C1Y—C2Y—C3Y	5.6 (3)
N2A—C11A—C12A—N3A	53.0 (2)	O1Y—C1Y—C2Y—C3Y	−174.5 (2)

(20120156_0m)

Crystal data

C41H57F2N6O21	V = 2204.38 (13) Å^3
Mr = 1007.93	Z = 2
Triclinic, P1	F(000) = 1062
a = 7.4031 (3) Å	Dx = 1.518 Mg m^−3
b = 9.7515 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 30.9801 (10) Å	µ = 0.13 mm^−1
α = 88.088 (2)°	T = 100 K
β = 85.673 (2)°	Needle, colorless
γ = 81.380 (2)°	0.21 × 0.08 × 0.05 mm

Data collection

CCD area detector diffractometer	4274 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.059
Graphite monochromator	θmax = 25.0°, θmin = 1.3°
phi and ω scans	h = −8→8
31596 measured reflections	k = −11→11
7784 independent reflections	l = −36→36

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.056P)^2 + 0.3322P] where P = (Fo^2 + 2Fc^2)/3
7784 reflections	(Δ/σ)max = 0.001
673 parameters	Δρmax = 0.41 e Å^−3
14 restraints	Δρmin = −0.31 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
H2B	0.333 (7)	0.926 (5)	0.9142 (16)	0.122 (19)*
H2A	0.325 (5)	0.835 (4)	0.9506 (12)	0.072 (15)*
O2S	0.3966 (3)	0.8792 (3)	0.93735 (9)	0.0513 (7)
O1Y	0.8893 (3)	0.2461 (2)	1.02422 (7)	0.0405 (6)
O3Y	0.7950 (3)	0.5381 (2)	0.95190 (7)	0.0511 (7)
H1'	0.8611	0.4888	0.9343	0.077*
O4Y	0.5320 (3)	0.3592 (2)	0.96084 (7)	0.0419 (6)
H4Y	0.4260	0.3433	0.9635	0.063*
O2Y	1.0077 (3)	0.3019 (2)	0.95873 (7)	0.0414 (6)
C1Y	0.8976 (4)	0.3251 (3)	0.99085 (10)	0.0293 (8)
C2Y	0.7658 (4)	0.4600 (3)	0.99086 (10)	0.0319 (8)
H2'	0.7906	0.5147	1.0151	0.038*
C3Y	0.5681 (4)	0.4335 (3)	0.99746 (9)	0.0293 (8)
H3'	0.5552	0.3750	1.0235	0.035*
O3X	0.5823 (3)	0.1571 (2)	0.43764 (7)	0.0369 (6)
H6'	0.6554	0.2116	0.4318	0.055*
O4X	0.6539 (2)	0.0815 (2)	0.52956 (6)	0.0296 (5)
H8'	0.7656	0.0702	0.5303	0.044*
O1S	0.3279 (4)	0.1470 (3)	0.97959 (8)	0.0450 (7)
O2A	1.2065 (4)	0.1025 (3)	0.88170 (8)	0.0639 (8)
H1	1.1627	0.1847	0.8802	0.096*
O1A	1.2958 (4)	−0.0690 (3)	0.83684 (9)	0.0705 (9)
F1A	0.7822 (3)	0.7158 (2)	0.75906 (6)	0.0520 (5)
O2B	0.3489 (3)	0.6531 (3)	0.67071 (8)	0.0521 (7)
O1B	0.2921 (5)	0.8080 (3)	0.72134 (9)	0.0818 (10)
F1B	0.8147 (3)	0.00155 (19)	0.77003 (5)	0.0505 (5)
O1X	0.9884 (3)	−0.0765 (2)	0.45757 (6)	0.0313 (5)
O2X	0.9322 (3)	0.1462 (2)	0.43767 (7)	0.0418 (6)
O1Z	0.1139 (3)	0.3142 (3)	0.52312 (7)	0.0418 (6)
O4Z	0.5887 (3)	0.3643 (2)	0.53742 (7)	0.0400 (6)
H12'	0.615 (5)	0.281 (4)	0.5310 (11)	0.060*
N2A	0.8575 (3)	0.6311 (3)	0.67358 (7)	0.0329 (7)
N1A	1.1772 (4)	0.1980 (3)	0.73092 (8)	0.0372 (6)
O3A	1.0445 (3)	0.3286 (3)	0.85514 (7)	0.0565 (7)
N2B	0.7639 (3)	0.0598 (2)	0.85922 (7)	0.0281 (6)
N3B	0.8142 (3)	−0.1320 (3)	0.93231 (7)	0.0352 (7)
H34	0.6979	−0.1417	0.9410	0.042*
H33	0.8888	−0.1853	0.9498	0.042*
O3B	0.5025 (3)	0.4101 (2)	0.68871 (7)	0.0444 (6)
O2Z	0.1984 (3)	0.3199 (3)	0.59078 (8)	0.0585 (7)
N3A	0.7474 (4)	0.7978 (3)	0.59967 (9)	0.0398 (8)
C12A	0.7312 (4)	0.8547 (3)	0.64372 (11)	0.0443 (9)
H13	0.6114	0.8458	0.6575	0.053*
H12	0.7427	0.9525	0.6418	0.053*
C11A	0.8768 (5)	0.7794 (3)	0.67058 (10)	0.0404 (9)
H10	0.9969	0.7904	0.6574	0.048*
H11	0.8645	0.8177	0.6993	0.048*
C8A	0.9284 (4)	0.5491 (3)	0.70795 (9)	0.0285 (8)
C9A	1.0300 (4)	0.4190 (3)	0.70216 (9)	0.0297 (8)
H8	1.0650	0.3890	0.6742	0.036*
C10A	1.0815 (4)	0.3314 (3)	0.73714 (9)	0.0278 (7)
C1A	1.2175 (4)	0.1148 (4)	0.76530 (11)	0.0414 (9)
H2	1.2771	0.0253	0.7602	0.050*
C2A	1.1764 (4)	0.1531 (4)	0.80742 (10)	0.0382 (9)
C3A	1.2312 (5)	0.0514 (5)	0.84246 (12)	0.0494 (10)
C15A	1.2331 (5)	0.1443 (4)	0.68672 (10)	0.0452 (7)
H4	1.2732	0.2179	0.6683	0.054*
H3	1.3354	0.0699	0.6882	0.054*
C16A	1.0805 (5)	0.0924 (4)	0.66773 (11)	0.0605 (10)
H5	1.0345	0.0246	0.6870	0.091*
H6	1.1230	0.0507	0.6405	0.091*
H7	0.9843	0.1682	0.6633	0.091*
C5A	1.0367 (4)	0.3767 (3)	0.77983 (9)	0.0320 (8)
C4A	1.0853 (4)	0.2871 (4)	0.81688 (11)	0.0383 (9)
C6A	0.9397 (4)	0.5104 (4)	0.78577 (10)	0.0368 (8)
H9	0.9113	0.5437	0.8136	0.044*
C7A	0.8873 (4)	0.5912 (3)	0.75141 (10)	0.0351 (8)
C13A	0.7483 (4)	0.6455 (3)	0.60107 (10)	0.0406 (9)
H16	0.7761	0.6102	0.5721	0.049*
H17	0.6271	0.6260	0.6110	0.049*
C14A	0.8859 (4)	0.5715 (3)	0.63048 (9)	0.0359 (8)
H19	0.8737	0.4738	0.6326	0.043*
H18	1.0088	0.5794	0.6184	0.043*
C3B	0.3466 (5)	0.6907 (4)	0.71129 (12)	0.0463 (9)
C2B	0.4164 (4)	0.5785 (3)	0.74194 (10)	0.0347 (8)
C4B	0.4923 (4)	0.4445 (3)	0.72801 (10)	0.0327 (8)
C5B	0.5596 (4)	0.3467 (3)	0.76188 (9)	0.0294 (8)
C6B	0.6495 (4)	0.2134 (3)	0.75146 (9)	0.0322 (8)
H21	0.6638	0.1864	0.7228	0.039*
C7B	0.7154 (4)	0.1241 (3)	0.78281 (10)	0.0312 (8)
C8B	0.6919 (4)	0.1536 (3)	0.82764 (9)	0.0277 (7)
C11B	0.7384 (5)	−0.0864 (3)	0.85643 (10)	0.0377 (8)
H30	0.7705	−0.1171	0.8270	0.045*
H29	0.6105	−0.0948	0.8635	0.045*
C12B	0.8556 (4)	−0.1783 (3)	0.88711 (9)	0.0377 (8)
H31	0.8332	−0.2733	0.8852	0.045*
H32	0.9839	−0.1756	0.8787	0.045*
C1B	0.4101 (4)	0.6100 (4)	0.78500 (11)	0.0425 (9)
H28	0.3611	0.6996	0.7931	0.051*
N1B	0.4705 (4)	0.5194 (3)	0.81605 (8)	0.0392 (7)
C10B	0.5440 (4)	0.3837 (3)	0.80550 (10)	0.0308 (8)
C13B	0.8394 (5)	0.0145 (3)	0.93556 (10)	0.0373 (8)
H36	0.9681	0.0222	0.9298	0.045*
H35	0.8030	0.0449	0.9648	0.045*
C14B	0.7290 (4)	0.1084 (3)	0.90421 (9)	0.0334 (8)
H37	0.5997	0.1124	0.9129	0.040*
H38	0.7595	0.2014	0.9054	0.040*
C9B	0.6035 (4)	0.2858 (3)	0.83745 (9)	0.0322 (8)
H22	0.5830	0.3103	0.8663	0.039*
C15B	0.4569 (5)	0.5708 (4)	0.86199 (10)	0.0503 (10)
H23	0.5571	0.5218	0.8775	0.060*
H24	0.4666	0.6689	0.8615	0.060*
C16B	0.2815 (6)	0.5480 (5)	0.88439 (13)	0.0742 (13)
H25	0.1830	0.5870	0.8672	0.111*
H26	0.2672	0.5919	0.9120	0.111*
H27	0.2797	0.4503	0.8886	0.111*
C1X	0.8834 (4)	0.0320 (3)	0.44884 (9)	0.0250 (7)
C2X	0.6776 (4)	0.0282 (3)	0.45211 (9)	0.0243 (7)
H5'	0.6538	−0.0440	0.4329	0.029*
C3X	0.6045 (3)	−0.0070 (3)	0.49800 (9)	0.0216 (7)
H7'	0.6548	−0.1031	0.5052	0.026*
C1Z	0.1923 (4)	0.3659 (3)	0.55439 (11)	0.0333 (8)
C2Z	0.2832 (4)	0.4898 (3)	0.53881 (9)	0.0315 (8)
H11'	0.1993	0.5524	0.5215	0.038*
C3Z	0.4582 (4)	0.4394 (3)	0.51077 (9)	0.0282 (7)
H13'	0.4301	0.3785	0.4884	0.034*
H15	0.863 (6)	0.817 (4)	0.5863 (12)	0.082 (13)*
H14	0.649 (5)	0.830 (4)	0.5860 (10)	0.056 (11)*
O3S	0.6622 (7)	0.2085 (5)	0.62770 (12)	0.173 (2)
H3A	0.6493	0.2493	0.6032	0.259*
H3B	0.6426	0.2701	0.6469	0.259*
H1B	0.214 (6)	0.193 (4)	0.9707 (12)	0.083 (15)*
H1A	0.356 (7)	0.068 (5)	0.9669 (16)	0.12 (2)*
H9'	0.074 (5)	0.233 (4)	0.5329 (12)	0.081 (14)*
H20	0.396 (5)	0.556 (4)	0.6688 (11)	0.063 (13)*
O3Z	0.3255 (3)	0.5618 (2)	0.57498 (7)	0.0463 (6)
H10'	0.3619	0.5056	0.5939	0.069*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O2S	0.0418 (16)	0.0528 (19)	0.0588 (18)	−0.0096 (14)	−0.0060 (14)	0.0240 (14)
O1Y	0.0354 (13)	0.0401 (15)	0.0438 (13)	−0.0014 (11)	−0.0050 (11)	0.0163 (11)
O3Y	0.0431 (16)	0.0450 (16)	0.0607 (16)	−0.0021 (12)	0.0045 (12)	0.0258 (13)
O4Y	0.0313 (13)	0.0465 (15)	0.0482 (14)	−0.0055 (11)	0.0002 (11)	−0.0144 (12)
O2Y	0.0351 (13)	0.0449 (16)	0.0403 (14)	0.0028 (12)	0.0058 (11)	−0.0009 (11)
C1Y	0.0214 (17)	0.031 (2)	0.0367 (19)	−0.0055 (15)	−0.0066 (15)	0.0000 (16)
C2Y	0.0292 (18)	0.029 (2)	0.0360 (18)	−0.0017 (16)	−0.0022 (14)	0.0064 (15)
C3Y	0.0327 (19)	0.0235 (19)	0.0315 (18)	−0.0037 (14)	−0.0030 (15)	0.0007 (15)
O3X	0.0238 (12)	0.0345 (14)	0.0526 (14)	−0.0077 (11)	−0.0063 (10)	0.0209 (11)
O4X	0.0149 (10)	0.0367 (14)	0.0381 (12)	−0.0044 (10)	−0.0035 (9)	−0.0057 (10)
O1S	0.0390 (16)	0.0474 (19)	0.0480 (15)	−0.0050 (14)	−0.0016 (12)	−0.0021 (14)
O2A	0.0687 (19)	0.082 (2)	0.0447 (16)	−0.0219 (18)	−0.0208 (14)	0.0332 (15)
O1A	0.0666 (19)	0.061 (2)	0.079 (2)	0.0027 (17)	−0.0167 (15)	0.0390 (17)
F1A	0.0683 (14)	0.0350 (13)	0.0487 (12)	0.0026 (11)	0.0036 (10)	−0.0058 (10)
O2B	0.0572 (17)	0.057 (2)	0.0402 (16)	−0.0042 (15)	−0.0074 (12)	0.0151 (14)
O1B	0.134 (3)	0.0415 (19)	0.0628 (18)	0.016 (2)	−0.0245 (18)	0.0125 (15)
F1B	0.0719 (14)	0.0332 (12)	0.0395 (11)	0.0107 (11)	0.0047 (10)	−0.0030 (9)
O1X	0.0176 (11)	0.0286 (14)	0.0481 (13)	−0.0039 (10)	−0.0036 (10)	−0.0002 (10)
O2X	0.0257 (12)	0.0384 (15)	0.0611 (15)	−0.0100 (11)	0.0009 (11)	0.0164 (12)
O1Z	0.0406 (14)	0.0365 (16)	0.0521 (15)	−0.0174 (12)	−0.0054 (12)	0.0011 (13)
O4Z	0.0405 (14)	0.0300 (14)	0.0478 (14)	0.0011 (13)	−0.0080 (11)	0.0047 (12)
N2A	0.0431 (17)	0.0264 (16)	0.0299 (15)	−0.0069 (13)	−0.0065 (12)	0.0055 (12)
N1A	0.0484 (15)	0.0273 (15)	0.0342 (12)	−0.0005 (12)	−0.0061 (12)	0.0091 (11)
O3A	0.0779 (19)	0.0683 (19)	0.0277 (14)	−0.0241 (15)	−0.0102 (13)	0.0071 (13)
N2B	0.0344 (15)	0.0212 (15)	0.0280 (14)	−0.0016 (12)	−0.0028 (11)	0.0011 (12)
N3B	0.0365 (16)	0.0327 (17)	0.0340 (15)	−0.0002 (13)	−0.0011 (12)	0.0102 (13)
O3B	0.0554 (15)	0.0491 (16)	0.0286 (13)	−0.0068 (13)	−0.0059 (11)	0.0035 (11)
O2Z	0.0802 (19)	0.0579 (18)	0.0410 (15)	−0.0280 (15)	0.0037 (13)	0.0092 (13)
N3A	0.0218 (17)	0.050 (2)	0.0473 (19)	−0.0057 (15)	−0.0082 (15)	0.0218 (16)
C12A	0.041 (2)	0.031 (2)	0.059 (2)	−0.0034 (18)	−0.0023 (18)	0.0119 (18)
C11A	0.050 (2)	0.029 (2)	0.045 (2)	−0.0125 (17)	−0.0101 (17)	0.0113 (16)
C8A	0.0289 (18)	0.027 (2)	0.0304 (18)	−0.0065 (16)	−0.0044 (14)	0.0055 (15)
C9A	0.0334 (19)	0.031 (2)	0.0253 (17)	−0.0057 (16)	−0.0019 (14)	0.0009 (15)
C10A	0.0284 (18)	0.027 (2)	0.0289 (18)	−0.0079 (15)	−0.0036 (14)	0.0059 (15)
C1A	0.040 (2)	0.031 (2)	0.052 (2)	−0.0050 (17)	−0.0069 (17)	0.0127 (18)
C2A	0.036 (2)	0.044 (2)	0.037 (2)	−0.0127 (18)	−0.0126 (16)	0.0196 (18)
C3A	0.039 (2)	0.065 (3)	0.048 (3)	−0.020 (2)	−0.0120 (19)	0.025 (2)
C15A	0.0591 (17)	0.0336 (16)	0.0395 (13)	0.0024 (14)	−0.0024 (13)	0.0058 (12)
C16A	0.081 (2)	0.050 (2)	0.054 (2)	−0.0178 (19)	−0.0044 (18)	−0.0011 (18)
C5A	0.0346 (19)	0.033 (2)	0.0311 (18)	−0.0142 (17)	−0.0066 (15)	0.0079 (16)
C4A	0.038 (2)	0.046 (3)	0.036 (2)	−0.0214 (19)	−0.0077 (16)	0.0101 (18)
C6A	0.045 (2)	0.040 (2)	0.0272 (18)	−0.0152 (19)	−0.0007 (15)	0.0000 (16)
C7A	0.038 (2)	0.025 (2)	0.042 (2)	−0.0037 (17)	0.0002 (16)	−0.0027 (16)
C13A	0.039 (2)	0.045 (2)	0.040 (2)	−0.0134 (18)	−0.0094 (16)	0.0128 (17)
C14A	0.041 (2)	0.035 (2)	0.0322 (18)	−0.0053 (17)	−0.0046 (15)	0.0050 (16)
C3B	0.050 (2)	0.046 (3)	0.042 (2)	−0.005 (2)	−0.0054 (18)	0.011 (2)
C2B	0.0317 (19)	0.034 (2)	0.036 (2)	0.0007 (17)	−0.0010 (15)	0.0081 (16)
C4B	0.0251 (18)	0.037 (2)	0.036 (2)	−0.0083 (16)	0.0015 (15)	0.0070 (17)
C5B	0.0279 (18)	0.027 (2)	0.0327 (18)	−0.0058 (16)	−0.0004 (14)	0.0056 (15)
C6B	0.0362 (19)	0.035 (2)	0.0256 (17)	−0.0068 (17)	−0.0002 (14)	−0.0019 (15)
C7B	0.0352 (19)	0.0218 (19)	0.0341 (19)	0.0017 (16)	0.0021 (15)	−0.0008 (15)
C8B	0.0233 (17)	0.030 (2)	0.0294 (18)	−0.0026 (15)	−0.0013 (14)	0.0028 (15)
C11B	0.049 (2)	0.026 (2)	0.0390 (19)	−0.0048 (17)	−0.0072 (16)	0.0030 (15)
C12B	0.043 (2)	0.028 (2)	0.039 (2)	0.0029 (17)	0.0009 (16)	0.0017 (16)
C1B	0.048 (2)	0.030 (2)	0.045 (2)	0.0064 (17)	−0.0015 (17)	0.0078 (17)
N1B	0.0539 (19)	0.0276 (18)	0.0310 (15)	0.0091 (15)	−0.0008 (13)	0.0026 (13)
C10B	0.0323 (19)	0.026 (2)	0.0336 (19)	−0.0023 (16)	0.0004 (15)	−0.0001 (15)
C13B	0.050 (2)	0.031 (2)	0.0326 (18)	−0.0079 (17)	−0.0081 (16)	0.0071 (15)
C14B	0.041 (2)	0.029 (2)	0.0280 (18)	−0.0021 (16)	−0.0002 (15)	0.0017 (15)
C9B	0.0348 (19)	0.033 (2)	0.0269 (17)	−0.0005 (17)	0.0003 (14)	0.0019 (15)
C15B	0.074 (3)	0.026 (2)	0.042 (2)	0.015 (2)	0.005 (2)	0.0007 (17)
C16B	0.074 (3)	0.083 (4)	0.064 (3)	−0.001 (3)	−0.010 (2)	−0.016 (2)
C1X	0.0236 (17)	0.027 (2)	0.0238 (16)	−0.0045 (16)	0.0009 (13)	0.0006 (14)
C2X	0.0195 (16)	0.0233 (18)	0.0297 (17)	−0.0036 (14)	0.0001 (13)	0.0043 (14)
C3X	0.0165 (15)	0.0183 (17)	0.0298 (16)	−0.0021 (14)	−0.0024 (13)	−0.0001 (13)
C1Z	0.0289 (19)	0.030 (2)	0.041 (2)	−0.0069 (16)	0.0048 (16)	−0.0066 (17)
C2Z	0.0334 (19)	0.027 (2)	0.0349 (18)	−0.0074 (16)	0.0022 (15)	−0.0046 (15)
C3Z	0.0318 (19)	0.0219 (18)	0.0315 (17)	−0.0054 (15)	−0.0021 (14)	−0.0021 (14)
O3S	0.231 (5)	0.155 (4)	0.104 (3)	0.062 (4)	−0.016 (3)	−0.007 (3)
O3Z	0.0557 (16)	0.0410 (15)	0.0445 (14)	−0.0179 (14)	0.0095 (12)	−0.0162 (12)

Geometric parameters (Å, º)

O2S—H2B	0.95 (5)	C1A—H2	0.9300
O2S—H2A	0.81 (4)	C2A—C4A	1.407 (5)
O1Y—C1Y	1.272 (3)	C2A—C3A	1.483 (5)
O3Y—C2Y	1.425 (3)	C15A—C16A	1.473 (4)
O3Y—H1'	0.8200	C15A—H4	0.9700
O4Y—C3Y	1.429 (3)	C15A—H3	0.9700
O4Y—H4Y	0.8200	C16A—H5	0.9600
O2Y—C1Y	1.242 (3)	C16A—H6	0.9600
C1Y—C2Y	1.516 (4)	C16A—H7	0.9600
C2Y—C3Y	1.522 (4)	C5A—C6A	1.402 (4)
C2Y—H2'	0.9800	C5A—C4A	1.453 (4)
C3Y—C3Y^i	1.523 (6)	C6A—C7A	1.348 (4)
C3Y—H3'	0.9800	C6A—H9	0.9300
O3X—C2X	1.422 (3)	C13A—C14A	1.505 (4)
O3X—H6'	0.8200	C13A—H16	0.9700
O4X—C3X	1.428 (3)	C13A—H17	0.9700
O4X—H8'	0.8200	C14A—H19	0.9700
O1S—H1B	0.95 (4)	C14A—H18	0.9700
O1S—H1A	0.87 (5)	C3B—C2B	1.483 (5)
O2A—C3A	1.318 (4)	C2B—C1B	1.375 (4)
O2A—H1	0.8200	C2B—C4B	1.411 (4)
O1A—C3A	1.213 (4)	C4B—C5B	1.459 (4)
F1A—C7A	1.359 (3)	C5B—C10B	1.402 (4)
O2B—C3B	1.320 (4)	C5B—C6B	1.405 (4)
O2B—H20	0.96 (4)	C6B—C7B	1.352 (4)
O1B—C3B	1.198 (4)	C6B—H21	0.9300
F1B—C7B	1.360 (3)	C7B—C8B	1.420 (4)
O1X—C1X	1.251 (3)	C8B—C9B	1.388 (4)
O2X—C1X	1.251 (3)	C11B—C12B	1.514 (4)
O1Z—C1Z	1.317 (4)	C11B—H30	0.9700
O1Z—H9'	0.92 (4)	C11B—H29	0.9700
O4Z—C3Z	1.422 (3)	C12B—H31	0.9700
O4Z—H12'	0.83 (4)	C12B—H32	0.9700
N2A—C8A	1.397 (3)	C1B—N1B	1.340 (4)
N2A—C14A	1.462 (4)	C1B—H28	0.9300
N2A—C11A	1.473 (4)	N1B—C10B	1.393 (4)
N1A—C1A	1.342 (4)	N1B—C15B	1.516 (4)
N1A—C10A	1.397 (4)	C10B—C9B	1.401 (4)
N1A—C15A	1.489 (4)	C13B—C14B	1.511 (4)
O3A—C4A	1.266 (4)	C13B—H36	0.9700
N2B—C8B	1.397 (4)	C13B—H35	0.9700
N2B—C11B	1.472 (4)	C14B—H37	0.9700
N2B—C14B	1.479 (4)	C14B—H38	0.9700
N3B—C13B	1.477 (4)	C9B—H22	0.9300
N3B—C12B	1.481 (4)	C15B—C16B	1.468 (5)
N3B—H34	0.9000	C15B—H23	0.9700
N3B—H33	0.9000	C15B—H24	0.9700
O3B—C4B	1.268 (3)	C16B—H25	0.9600
O2Z—C1Z	1.201 (4)	C16B—H26	0.9600
N3A—C12A	1.480 (4)	C16B—H27	0.9600
N3A—C13A	1.483 (4)	C1X—C2X	1.525 (4)
N3A—H15	0.97 (4)	C2X—C3X	1.529 (4)
N3A—H14	0.88 (3)	C2X—H5'	0.9800
C12A—C11A	1.500 (4)	C3X—C3X^ii	1.528 (5)
C12A—H13	0.9700	C3X—H7'	0.9800
C12A—H12	0.9700	C1Z—C2Z	1.517 (4)
C11A—H10	0.9700	C2Z—O3Z	1.420 (3)
C11A—H11	0.9700	C2Z—C3Z	1.530 (4)
C8A—C9A	1.385 (4)	C2Z—H11'	0.9800
C8A—C7A	1.418 (4)	C3Z—C3Z^iii	1.526 (5)
C9A—C10A	1.397 (4)	C3Z—H13'	0.9800
C9A—H8	0.9300	O3S—H3A	0.8500
C10A—C5A	1.408 (4)	O3S—H3B	0.8498
C1A—C2A	1.369 (4)	O3Z—H10'	0.8200
H2B—O2S—H2A	106 (4)	N2A—C14A—H19	109.6
C2Y—O3Y—H1'	109.5	C13A—C14A—H19	109.6
C3Y—O4Y—H4Y	109.5	N2A—C14A—H18	109.6
O2Y—C1Y—O1Y	125.2 (3)	C13A—C14A—H18	109.6
O2Y—C1Y—C2Y	117.5 (3)	H19—C14A—H18	108.1
O1Y—C1Y—C2Y	117.3 (3)	O1B—C3B—O2B	120.6 (3)
O3Y—C2Y—C1Y	110.5 (2)	O1B—C3B—C2B	124.3 (4)
O3Y—C2Y—C3Y	111.2 (2)	O2B—C3B—C2B	115.0 (4)
C1Y—C2Y—C3Y	111.1 (2)	C1B—C2B—C4B	120.1 (3)
O3Y—C2Y—H2'	108.0	C1B—C2B—C3B	117.7 (3)
C1Y—C2Y—H2'	108.0	C4B—C2B—C3B	122.2 (3)
C3Y—C2Y—H2'	108.0	O3B—C4B—C2B	122.8 (3)
O4Y—C3Y—C2Y	107.2 (2)	O3B—C4B—C5B	121.6 (3)
O4Y—C3Y—C3Y^i	110.5 (3)	C2B—C4B—C5B	115.7 (3)
C2Y—C3Y—C3Y^i	112.9 (3)	C10B—C5B—C6B	117.7 (3)
O4Y—C3Y—H3'	108.7	C10B—C5B—C4B	121.6 (3)
C2Y—C3Y—H3'	108.7	C6B—C5B—C4B	120.7 (3)
C3Y^i—C3Y—H3'	108.7	C7B—C6B—C5B	120.6 (3)
C2X—O3X—H6'	109.5	C7B—C6B—H21	119.7
C3X—O4X—H8'	109.5	C5B—C6B—H21	119.7
H1B—O1S—H1A	109 (4)	C6B—C7B—F1B	117.3 (3)
C3A—O2A—H1	109.5	C6B—C7B—C8B	123.7 (3)
C3B—O2B—H20	109 (2)	F1B—C7B—C8B	119.0 (3)
C1Z—O1Z—H9'	109 (2)	C9B—C8B—N2B	122.5 (3)
C3Z—O4Z—H12'	113 (3)	C9B—C8B—C7B	115.1 (3)
C8A—N2A—C14A	117.4 (3)	N2B—C8B—C7B	122.3 (3)
C8A—N2A—C11A	119.8 (2)	N2B—C11B—C12B	111.3 (3)
C14A—N2A—C11A	109.9 (2)	N2B—C11B—H30	109.4
C1A—N1A—C10A	119.7 (3)	C12B—C11B—H30	109.4
C1A—N1A—C15A	118.8 (3)	N2B—C11B—H29	109.4
C10A—N1A—C15A	121.5 (2)	C12B—C11B—H29	109.4
C8B—N2B—C11B	118.1 (2)	H30—C11B—H29	108.0
C8B—N2B—C14B	115.1 (2)	N3B—C12B—C11B	111.0 (3)
C11B—N2B—C14B	111.3 (2)	N3B—C12B—H31	109.4
C13B—N3B—C12B	110.3 (2)	C11B—C12B—H31	109.4
C13B—N3B—H34	109.6	N3B—C12B—H32	109.4
C12B—N3B—H34	109.6	C11B—C12B—H32	109.4
C13B—N3B—H33	109.6	H31—C12B—H32	108.0
C12B—N3B—H33	109.6	N1B—C1B—C2B	124.0 (3)
H34—N3B—H33	108.1	N1B—C1B—H28	118.0
C12A—N3A—C13A	111.5 (2)	C2B—C1B—H28	118.0
C12A—N3A—H15	106 (2)	C1B—N1B—C10B	120.0 (3)
C13A—N3A—H15	109 (2)	C1B—N1B—C15B	117.7 (3)
C12A—N3A—H14	110 (2)	C10B—N1B—C15B	122.3 (2)
C13A—N3A—H14	104 (2)	N1B—C10B—C9B	121.2 (3)
H15—N3A—H14	116 (3)	N1B—C10B—C5B	118.6 (3)
N3A—C12A—C11A	110.7 (3)	C9B—C10B—C5B	120.2 (3)
N3A—C12A—H13	109.5	N3B—C13B—C14B	112.2 (2)
C11A—C12A—H13	109.5	N3B—C13B—H36	109.2
N3A—C12A—H12	109.5	C14B—C13B—H36	109.2
C11A—C12A—H12	109.5	N3B—C13B—H35	109.2
H13—C12A—H12	108.1	C14B—C13B—H35	109.2
N2A—C11A—C12A	109.1 (3)	H36—C13B—H35	107.9
N2A—C11A—H10	109.9	N2B—C14B—C13B	112.1 (3)
C12A—C11A—H10	109.9	N2B—C14B—H37	109.2
N2A—C11A—H11	109.9	C13B—C14B—H37	109.2
C12A—C11A—H11	109.9	N2B—C14B—H38	109.2
H10—C11A—H11	108.3	C13B—C14B—H38	109.2
C9A—C8A—N2A	122.6 (3)	H37—C14B—H38	107.9
C9A—C8A—C7A	116.2 (3)	C8B—C9B—C10B	122.6 (3)
N2A—C8A—C7A	121.1 (3)	C8B—C9B—H22	118.7
C8A—C9A—C10A	121.9 (3)	C10B—C9B—H22	118.7
C8A—C9A—H8	119.0	C16B—C15B—N1B	110.2 (3)
C10A—C9A—H8	119.0	C16B—C15B—H23	109.6
N1A—C10A—C9A	121.4 (3)	N1B—C15B—H23	109.6
N1A—C10A—C5A	118.5 (3)	C16B—C15B—H24	109.6
C9A—C10A—C5A	120.1 (3)	N1B—C15B—H24	109.6
N1A—C1A—C2A	124.2 (3)	H23—C15B—H24	108.1
N1A—C1A—H2	117.9	C15B—C16B—H25	109.5
C2A—C1A—H2	117.9	C15B—C16B—H26	109.5
C1A—C2A—C4A	120.1 (3)	H25—C16B—H26	109.5
C1A—C2A—C3A	118.8 (4)	C15B—C16B—H27	109.5
C4A—C2A—C3A	121.1 (3)	H25—C16B—H27	109.5
O1A—C3A—O2A	120.9 (3)	H26—C16B—H27	109.5
O1A—C3A—C2A	124.7 (4)	O1X—C1X—O2X	125.5 (3)
O2A—C3A—C2A	114.5 (4)	O1X—C1X—C2X	118.5 (3)
C16A—C15A—N1A	111.2 (3)	O2X—C1X—C2X	116.0 (3)
C16A—C15A—H4	109.4	O3X—C2X—C1X	110.2 (2)
N1A—C15A—H4	109.4	O3X—C2X—C3X	110.0 (2)
C16A—C15A—H3	109.4	C1X—C2X—C3X	112.5 (2)
N1A—C15A—H3	109.4	O3X—C2X—H5'	108.0
H4—C15A—H3	108.0	C1X—C2X—H5'	108.0
C15A—C16A—H5	109.5	C3X—C2X—H5'	108.0
C15A—C16A—H6	109.5	O4X—C3X—C3X^ii	106.6 (3)
H5—C16A—H6	109.5	O4X—C3X—C2X	112.5 (2)
C15A—C16A—H7	109.5	C3X^ii—C3X—C2X	111.8 (3)
H5—C16A—H7	109.5	O4X—C3X—H7'	108.6
H6—C16A—H7	109.5	C3X^ii—C3X—H7'	108.6
C6A—C5A—C10A	118.1 (3)	C2X—C3X—H7'	108.6
C6A—C5A—C4A	120.5 (3)	O2Z—C1Z—O1Z	125.3 (3)
C10A—C5A—C4A	121.4 (3)	O2Z—C1Z—C2Z	122.7 (3)
O3A—C4A—C2A	123.0 (3)	O1Z—C1Z—C2Z	112.0 (3)
O3A—C4A—C5A	121.0 (3)	O3Z—C2Z—C1Z	109.7 (2)
C2A—C4A—C5A	116.0 (3)	O3Z—C2Z—C3Z	110.2 (2)
C7A—C6A—C5A	120.5 (3)	C1Z—C2Z—C3Z	109.2 (2)
C7A—C6A—H9	119.8	O3Z—C2Z—H11'	109.3
C5A—C6A—H9	119.8	C1Z—C2Z—H11'	109.3
C6A—C7A—F1A	118.1 (3)	C3Z—C2Z—H11'	109.3
C6A—C7A—C8A	123.2 (3)	O4Z—C3Z—C3Z^iii	108.2 (3)
F1A—C7A—C8A	118.7 (3)	O4Z—C3Z—C2Z	108.9 (2)
N3A—C13A—C14A	112.3 (3)	C3Z^iii—C3Z—C2Z	111.5 (3)
N3A—C13A—H16	109.1	O4Z—C3Z—H13'	109.4
C14A—C13A—H16	109.1	C3Z^iii—C3Z—H13'	109.4
N3A—C13A—H17	109.1	C2Z—C3Z—H13'	109.4
C14A—C13A—H17	109.1	H3A—O3S—H3B	107.7
H16—C13A—H17	107.9	C2Z—O3Z—H10'	109.5
N2A—C14A—C13A	110.4 (3)
O2Y—C1Y—C2Y—O3Y	0.2 (4)	C1B—C2B—C4B—O3B	−179.6 (3)
O1Y—C1Y—C2Y—O3Y	178.6 (2)	C3B—C2B—C4B—O3B	−1.6 (5)
O2Y—C1Y—C2Y—C3Y	124.1 (3)	C1B—C2B—C4B—C5B	0.4 (4)
O1Y—C1Y—C2Y—C3Y	−57.5 (3)	C3B—C2B—C4B—C5B	178.3 (3)
O3Y—C2Y—C3Y—O4Y	59.2 (3)	O3B—C4B—C5B—C10B	−178.3 (3)
C1Y—C2Y—C3Y—O4Y	−64.3 (3)	C2B—C4B—C5B—C10B	1.7 (4)
O3Y—C2Y—C3Y—C3Y^i	−62.7 (4)	O3B—C4B—C5B—C6B	4.4 (4)
C1Y—C2Y—C3Y—C3Y^i	173.8 (3)	C2B—C4B—C5B—C6B	−175.5 (3)
C13A—N3A—C12A—C11A	53.8 (4)	C10B—C5B—C6B—C7B	1.1 (4)
C8A—N2A—C11A—C12A	−157.1 (3)	C4B—C5B—C6B—C7B	178.5 (3)
C14A—N2A—C11A—C12A	62.6 (3)	C5B—C6B—C7B—F1B	−174.4 (3)
N3A—C12A—C11A—N2A	−59.5 (3)	C5B—C6B—C7B—C8B	3.3 (5)
C14A—N2A—C8A—C9A	3.2 (4)	C11B—N2B—C8B—C9B	138.5 (3)
C11A—N2A—C8A—C9A	−134.3 (3)	C14B—N2B—C8B—C9B	3.7 (4)
C14A—N2A—C8A—C7A	−171.8 (3)	C11B—N2B—C8B—C7B	−46.2 (4)
C11A—N2A—C8A—C7A	50.7 (4)	C14B—N2B—C8B—C7B	179.0 (3)
N2A—C8A—C9A—C10A	−172.2 (3)	C6B—C7B—C8B—C9B	−3.4 (4)
C7A—C8A—C9A—C10A	3.0 (4)	F1B—C7B—C8B—C9B	174.3 (3)
C1A—N1A—C10A—C9A	−177.2 (3)	C6B—C7B—C8B—N2B	−179.1 (3)
C15A—N1A—C10A—C9A	1.6 (4)	F1B—C7B—C8B—N2B	−1.4 (4)
C1A—N1A—C10A—C5A	2.7 (4)	C8B—N2B—C11B—C12B	168.5 (3)
C15A—N1A—C10A—C5A	−178.5 (3)	C14B—N2B—C11B—C12B	−55.1 (3)
C8A—C9A—C10A—N1A	177.3 (3)	C13B—N3B—C12B—C11B	−56.6 (3)
C8A—C9A—C10A—C5A	−2.6 (4)	N2B—C11B—C12B—N3B	57.4 (3)
C10A—N1A—C1A—C2A	−2.5 (5)	C4B—C2B—C1B—N1B	−1.1 (5)
C15A—N1A—C1A—C2A	178.8 (3)	C3B—C2B—C1B—N1B	−179.1 (3)
N1A—C1A—C2A—C4A	0.4 (5)	C2B—C1B—N1B—C10B	−0.4 (5)
N1A—C1A—C2A—C3A	−179.1 (3)	C2B—C1B—N1B—C15B	179.0 (3)
C1A—C2A—C3A—O1A	−7.1 (5)	C1B—N1B—C10B—C9B	−178.2 (3)
C4A—C2A—C3A—O1A	173.4 (3)	C15B—N1B—C10B—C9B	2.4 (4)
C1A—C2A—C3A—O2A	172.1 (3)	C1B—N1B—C10B—C5B	2.4 (4)
C4A—C2A—C3A—O2A	−7.4 (4)	C15B—N1B—C10B—C5B	−176.9 (3)
C1A—N1A—C15A—C16A	97.1 (3)	C6B—C5B—C10B—N1B	174.2 (3)
C10A—N1A—C15A—C16A	−81.7 (4)	C4B—C5B—C10B—N1B	−3.1 (4)
N1A—C10A—C5A—C6A	−179.7 (3)	C6B—C5B—C10B—C9B	−5.1 (4)
C9A—C10A—C5A—C6A	0.2 (4)	C4B—C5B—C10B—C9B	177.5 (3)
N1A—C10A—C5A—C4A	−1.0 (4)	C12B—N3B—C13B—C14B	54.6 (3)
C9A—C10A—C5A—C4A	178.9 (3)	C8B—N2B—C14B—C13B	−169.3 (2)
C1A—C2A—C4A—O3A	−179.7 (3)	C11B—N2B—C14B—C13B	52.9 (3)
C3A—C2A—C4A—O3A	−0.3 (5)	N3B—C13B—C14B—N2B	−53.1 (4)
C1A—C2A—C4A—C5A	1.3 (4)	N2B—C8B—C9B—C10B	174.8 (3)
C3A—C2A—C4A—C5A	−179.2 (3)	C7B—C8B—C9B—C10B	−0.8 (4)
C6A—C5A—C4A—O3A	−1.3 (4)	N1B—C10B—C9B—C8B	−174.2 (3)
C10A—C5A—C4A—O3A	−180.0 (3)	C5B—C10B—C9B—C8B	5.1 (4)
C6A—C5A—C4A—C2A	177.7 (3)	C1B—N1B—C15B—C16B	90.9 (4)
C10A—C5A—C4A—C2A	−1.0 (4)	C10B—N1B—C15B—C16B	−89.7 (4)
C10A—C5A—C6A—C7A	1.7 (4)	O1X—C1X—C2X—O3X	−175.2 (2)
C4A—C5A—C6A—C7A	−177.0 (3)	O2X—C1X—C2X—O3X	5.1 (4)
C5A—C6A—C7A—F1A	175.3 (3)	O1X—C1X—C2X—C3X	61.5 (4)
C5A—C6A—C7A—C8A	−1.3 (5)	O2X—C1X—C2X—C3X	−118.1 (3)
C9A—C8A—C7A—C6A	−1.0 (4)	O3X—C2X—C3X—O4X	−70.2 (3)
N2A—C8A—C7A—C6A	174.2 (3)	C1X—C2X—C3X—O4X	53.1 (3)
C9A—C8A—C7A—F1A	−177.6 (2)	O3X—C2X—C3X—C3X^ii	49.7 (4)
N2A—C8A—C7A—F1A	−2.3 (4)	C1X—C2X—C3X—C3X^ii	173.0 (3)
C12A—N3A—C13A—C14A	−50.9 (4)	O2Z—C1Z—C2Z—O3Z	−16.4 (4)
C8A—N2A—C14A—C13A	159.1 (3)	O1Z—C1Z—C2Z—O3Z	165.8 (3)
C11A—N2A—C14A—C13A	−59.5 (3)	O2Z—C1Z—C2Z—C3Z	104.4 (4)
N3A—C13A—C14A—N2A	53.7 (3)	O1Z—C1Z—C2Z—C3Z	−73.4 (3)
O1B—C3B—C2B—C1B	3.0 (5)	O3Z—C2Z—C3Z—O4Z	52.1 (3)
O2B—C3B—C2B—C1B	−177.3 (3)	C1Z—C2Z—C3Z—O4Z	−68.3 (3)
O1B—C3B—C2B—C4B	−175.0 (4)	O3Z—C2Z—C3Z—C3Z^iii	−67.2 (4)
O2B—C3B—C2B—C4B	4.7 (5)	C1Z—C2Z—C3Z—C3Z^iii	172.3 (3)

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1.

(20120175_0m)

Crystal data

C23H26FN3O7	Z = 4
Mr = 475.47	F(000) = 1000
Monoclinic, P21/c	Dx = 1.434 Mg m^−3
a = 8.0761 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.7184 (3) Å	µ = 0.11 mm^−1
c = 18.7770 (4) Å	T = 100 K
β = 99.269 (1)°	Block, colorless
V = 2202.83 (8) Å^3	0.42 × 0.32 × 0.21 mm

Data collection

CCD area detector diffractometer	3253 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
Graphite monochromator	θmax = 25.0°, θmin = 1.8°
phi and ω scans	h = −9→9
31912 measured reflections	k = −17→17
3883 independent reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0403P)^2 + 0.9507P] where P = (Fo^2 + 2Fc^2)/3
3883 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.42326 (10)	0.81417 (6)	0.38762 (4)	0.0202 (2)
O2	−0.20034 (17)	0.83988 (10)	0.64181 (6)	0.0432 (4)
H1	−0.100 (3)	0.8235 (16)	0.6309 (13)	0.065*
O1	−0.42529 (15)	0.91128 (9)	0.58481 (6)	0.0378 (3)
O3	0.04864 (13)	0.81039 (7)	0.57741 (5)	0.0233 (3)
N3	0.30604 (16)	0.83197 (8)	0.11748 (7)	0.0169 (3)
O2'	0.53093 (12)	0.84794 (7)	1.02601 (5)	0.0226 (3)
O1'	0.38449 (12)	0.88257 (7)	0.91781 (6)	0.0233 (3)
O3'	1.12728 (13)	0.87721 (8)	0.98336 (6)	0.0241 (3)
H3'	1.215 (2)	0.8799 (12)	0.9569 (10)	0.036*
O1S	0.30291 (15)	0.44256 (9)	0.34929 (6)	0.0296 (3)
H1B	0.333 (3)	0.4109 (14)	0.3878 (11)	0.044*
H1A	0.328 (3)	0.4978 (15)	0.3654 (11)	0.044*
N2	0.23123 (15)	0.86103 (8)	0.25962 (6)	0.0164 (3)
N1	−0.22735 (15)	0.91939 (8)	0.39439 (6)	0.0166 (3)
C12	0.39814 (18)	0.78183 (10)	0.18061 (7)	0.0174 (3)
H12	0.4989	0.8149	0.2005	0.021*
H13	0.4311	0.7224	0.1654	0.021*
C3	−0.2865 (2)	0.88043 (12)	0.58381 (9)	0.0292 (4)
C2	−0.19933 (19)	0.88385 (10)	0.52005 (8)	0.0201 (3)
C4	−0.03410 (19)	0.84825 (10)	0.52170 (8)	0.0186 (3)
C5	0.03497 (18)	0.85737 (9)	0.45542 (7)	0.0164 (3)
C6	0.20201 (18)	0.83173 (10)	0.45275 (8)	0.0172 (3)
H9	0.2718	0.8128	0.4944	0.021*
C7	0.25997 (17)	0.83500 (9)	0.38897 (8)	0.0165 (3)
C8	0.16021 (18)	0.86086 (9)	0.32319 (7)	0.0155 (3)
C14	0.13694 (19)	0.90895 (10)	0.19760 (8)	0.0199 (3)
H2'	0.1004	0.9676	0.2128	0.024*
H1'	0.0383	0.8741	0.1778	0.024*
C13	0.2475 (2)	0.92176 (10)	0.14082 (8)	0.0202 (3)
H17	0.1854	0.9532	0.0996	0.024*
H16	0.3437	0.9588	0.1601	0.024*
C10	−0.06431 (18)	0.88930 (9)	0.39175 (8)	0.0158 (3)
C1	−0.28645 (19)	0.91834 (10)	0.45688 (8)	0.0186 (3)
H2	−0.3927	0.9423	0.4577	0.022*
C15	−0.33573 (18)	0.95418 (10)	0.32862 (8)	0.0182 (3)
H3	−0.4511	0.9562	0.3370	0.022*
H4	−0.3304	0.9126	0.2890	0.022*
C16	−0.2840 (2)	1.04770 (10)	0.30770 (8)	0.0241 (4)
H5	−0.2821	1.0883	0.3478	0.036*
H7	−0.3628	1.0695	0.2675	0.036*
H6	−0.1742	1.0448	0.2944	0.036*
C9	−0.00224 (18)	0.88868 (9)	0.32601 (8)	0.0163 (3)
H8	−0.0711	0.9072	0.2840	0.020*
C11	0.28642 (18)	0.77126 (10)	0.23757 (8)	0.0172 (3)
H11	0.1892	0.7349	0.2185	0.021*
H10	0.3474	0.7400	0.2792	0.021*
C7'	0.51952 (18)	0.86369 (10)	0.95935 (8)	0.0175 (3)
C1'	0.67732 (18)	0.85957 (9)	0.92638 (8)	0.0164 (3)
C2'	0.83346 (18)	0.86716 (10)	0.96962 (8)	0.0169 (3)
H4'	0.8407	0.8720	1.0194	0.020*
C3'	0.97903 (17)	0.86753 (10)	0.93876 (8)	0.0168 (3)
C4'	0.96881 (18)	0.85723 (10)	0.86446 (8)	0.0178 (3)
H7'	1.0659	0.8567	0.8437	0.021*
C5'	0.81307 (19)	0.84775 (10)	0.82154 (8)	0.0201 (3)
H6'	0.8060	0.8398	0.7720	0.024*
C6'	0.66806 (18)	0.85010 (10)	0.85203 (8)	0.0194 (3)
H5'	0.5640	0.8453	0.8227	0.023*
H14	0.380 (2)	0.8405 (12)	0.0816 (10)	0.037 (5)*
H15	0.211 (2)	0.7988 (12)	0.0961 (10)	0.032 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0133 (4)	0.0278 (5)	0.0200 (4)	0.0019 (3)	0.0040 (3)	0.0019 (4)
O2	0.0363 (8)	0.0793 (10)	0.0165 (6)	0.0269 (7)	0.0117 (6)	0.0132 (6)
O1	0.0320 (7)	0.0593 (8)	0.0255 (7)	0.0200 (6)	0.0146 (5)	0.0078 (6)
O3	0.0225 (6)	0.0353 (6)	0.0120 (5)	0.0082 (5)	0.0023 (4)	0.0025 (4)
N3	0.0156 (7)	0.0215 (7)	0.0146 (6)	−0.0002 (5)	0.0048 (5)	−0.0003 (5)
O2'	0.0175 (6)	0.0330 (6)	0.0189 (6)	−0.0016 (5)	0.0072 (4)	0.0001 (5)
O1'	0.0119 (5)	0.0315 (6)	0.0265 (6)	0.0008 (4)	0.0033 (5)	0.0031 (5)
O3'	0.0099 (5)	0.0434 (7)	0.0186 (6)	−0.0002 (5)	0.0016 (5)	0.0010 (5)
O1S	0.0340 (7)	0.0324 (7)	0.0220 (6)	0.0021 (5)	0.0031 (5)	−0.0001 (5)
N2	0.0181 (6)	0.0181 (6)	0.0138 (6)	0.0031 (5)	0.0052 (5)	0.0019 (5)
N1	0.0163 (6)	0.0195 (6)	0.0143 (6)	0.0017 (5)	0.0033 (5)	0.0001 (5)
C12	0.0159 (7)	0.0191 (7)	0.0172 (7)	0.0020 (6)	0.0029 (6)	−0.0005 (6)
C3	0.0283 (9)	0.0421 (10)	0.0182 (8)	0.0103 (8)	0.0070 (7)	0.0025 (7)
C2	0.0209 (8)	0.0254 (8)	0.0150 (7)	0.0038 (6)	0.0054 (6)	−0.0014 (6)
C4	0.0208 (8)	0.0210 (7)	0.0137 (7)	0.0004 (6)	0.0020 (6)	−0.0025 (6)
C5	0.0179 (8)	0.0170 (7)	0.0143 (7)	−0.0002 (6)	0.0024 (6)	−0.0011 (6)
C6	0.0172 (8)	0.0192 (7)	0.0143 (7)	0.0008 (6)	−0.0004 (6)	0.0009 (6)
C7	0.0121 (7)	0.0176 (7)	0.0204 (8)	−0.0002 (6)	0.0044 (6)	−0.0011 (6)
C8	0.0175 (8)	0.0139 (7)	0.0158 (7)	−0.0015 (6)	0.0043 (6)	0.0007 (6)
C14	0.0210 (8)	0.0215 (8)	0.0181 (8)	0.0058 (6)	0.0059 (6)	0.0038 (6)
C13	0.0239 (8)	0.0199 (8)	0.0180 (8)	0.0036 (6)	0.0066 (6)	0.0028 (6)
C10	0.0164 (7)	0.0142 (7)	0.0170 (7)	−0.0003 (6)	0.0036 (6)	−0.0015 (6)
C1	0.0183 (8)	0.0208 (8)	0.0178 (8)	0.0024 (6)	0.0062 (6)	−0.0021 (6)
C15	0.0163 (8)	0.0233 (8)	0.0147 (7)	0.0034 (6)	0.0018 (6)	0.0012 (6)
C16	0.0268 (9)	0.0229 (8)	0.0229 (8)	0.0053 (7)	0.0048 (7)	0.0028 (6)
C9	0.0182 (8)	0.0164 (7)	0.0141 (7)	0.0007 (6)	0.0014 (6)	0.0010 (6)
C11	0.0180 (8)	0.0174 (7)	0.0162 (7)	0.0025 (6)	0.0030 (6)	0.0006 (6)
C7'	0.0142 (8)	0.0177 (7)	0.0206 (8)	−0.0020 (6)	0.0028 (6)	−0.0006 (6)
C1'	0.0144 (7)	0.0162 (7)	0.0187 (8)	−0.0006 (6)	0.0032 (6)	0.0023 (6)
C2'	0.0166 (8)	0.0215 (8)	0.0130 (7)	0.0011 (6)	0.0041 (6)	0.0019 (6)
C3'	0.0120 (7)	0.0189 (7)	0.0187 (7)	0.0010 (6)	0.0004 (6)	0.0017 (6)
C4'	0.0143 (7)	0.0211 (8)	0.0198 (8)	0.0010 (6)	0.0082 (6)	0.0016 (6)
C5'	0.0221 (8)	0.0244 (8)	0.0143 (7)	−0.0017 (6)	0.0043 (6)	−0.0010 (6)
C6'	0.0143 (8)	0.0240 (8)	0.0191 (8)	−0.0035 (6)	0.0003 (6)	−0.0001 (6)

Geometric parameters (Å, º)

F1—C7	1.3580 (16)	C6—H9	0.9300
O2—C3	1.335 (2)	C7—C8	1.414 (2)
O2—H1	0.90 (3)	C8—C9	1.384 (2)
O1—C3	1.212 (2)	C14—C13	1.509 (2)
O3—C4	1.2752 (18)	C14—H2'	0.9700
N3—C12	1.4896 (18)	C14—H1'	0.9700
N3—C13	1.4928 (18)	C13—H17	0.9700
N3—H14	0.98 (2)	C13—H16	0.9700
N3—H15	0.940 (19)	C10—C9	1.405 (2)
O2'—C7'	1.2616 (17)	C1—H2	0.9300
O1'—C7'	1.2653 (17)	C15—C16	1.509 (2)
O3'—C3'	1.3535 (17)	C15—H3	0.9700
O3'—H3'	0.93 (2)	C15—H4	0.9700
O1S—H1B	0.86 (2)	C16—H5	0.9600
O1S—H1A	0.88 (2)	C16—H7	0.9600
N2—C8	1.4050 (18)	C16—H6	0.9600
N2—C14	1.4655 (18)	C9—H8	0.9300
N2—C11	1.4749 (18)	C11—H11	0.9700
N1—C1	1.3361 (18)	C11—H10	0.9700
N1—C10	1.3976 (18)	C7'—C1'	1.505 (2)
N1—C15	1.4850 (18)	C1'—C2'	1.390 (2)
C12—C11	1.5142 (19)	C1'—C6'	1.393 (2)
C12—H12	0.9700	C2'—C3'	1.392 (2)
C12—H13	0.9700	C2'—H4'	0.9300
C3—C2	1.484 (2)	C3'—C4'	1.393 (2)
C2—C1	1.375 (2)	C4'—C5'	1.387 (2)
C2—C4	1.429 (2)	C4'—H7'	0.9300
C4—C5	1.450 (2)	C5'—C6'	1.384 (2)
C5—C10	1.409 (2)	C5'—H6'	0.9300
C5—C6	1.409 (2)	C6'—H5'	0.9300
C6—C7	1.355 (2)
C3—O2—H1	107.8 (15)	N3—C13—H16	109.6
C12—N3—C13	110.25 (11)	C14—C13—H16	109.6
C12—N3—H14	109.4 (11)	H17—C13—H16	108.1
C13—N3—H14	110.2 (11)	N1—C10—C9	120.31 (13)
C12—N3—H15	110.5 (11)	N1—C10—C5	119.10 (12)
C13—N3—H15	108.1 (11)	C9—C10—C5	120.57 (13)
H14—N3—H15	108.5 (15)	N1—C1—C2	123.81 (14)
C3'—O3'—H3'	110.4 (11)	N1—C1—H2	118.1
H1B—O1S—H1A	101.2 (19)	C2—C1—H2	118.1
C8—N2—C14	116.42 (11)	N1—C15—C16	112.35 (12)
C8—N2—C11	114.84 (11)	N1—C15—H3	109.1
C14—N2—C11	110.47 (11)	C16—C15—H3	109.1
C1—N1—C10	119.96 (12)	N1—C15—H4	109.1
C1—N1—C15	119.22 (12)	C16—C15—H4	109.1
C10—N1—C15	120.81 (11)	H3—C15—H4	107.9
N3—C12—C11	109.57 (11)	C15—C16—H5	109.5
N3—C12—H12	109.8	C15—C16—H7	109.5
C11—C12—H12	109.8	H5—C16—H7	109.5
N3—C12—H13	109.8	C15—C16—H6	109.5
C11—C12—H13	109.8	H5—C16—H6	109.5
H12—C12—H13	108.2	H7—C16—H6	109.5
O1—C3—O2	121.10 (15)	C8—C9—C10	120.68 (13)
O1—C3—C2	124.02 (15)	C8—C9—H8	119.7
O2—C3—C2	114.87 (14)	C10—C9—H8	119.7
C1—C2—C4	120.00 (13)	N2—C11—C12	110.35 (11)
C1—C2—C3	117.72 (14)	N2—C11—H11	109.6
C4—C2—C3	122.18 (13)	C12—C11—H11	109.6
O3—C4—C2	122.81 (13)	N2—C11—H10	109.6
O3—C4—C5	121.43 (13)	C12—C11—H10	109.6
C2—C4—C5	115.76 (13)	H11—C11—H10	108.1
C10—C5—C6	118.44 (13)	O2'—C7'—O1'	124.75 (13)
C10—C5—C4	120.95 (13)	O2'—C7'—C1'	117.99 (13)
C6—C5—C4	120.57 (13)	O1'—C7'—C1'	117.26 (12)
C7—C6—C5	119.39 (13)	C2'—C1'—C6'	119.39 (13)
C7—C6—H9	120.3	C2'—C1'—C7'	120.33 (13)
C5—C6—H9	120.3	C6'—C1'—C7'	120.26 (13)
C6—C7—F1	118.89 (13)	C1'—C2'—C3'	120.31 (13)
C6—C7—C8	123.52 (13)	C1'—C2'—H4'	119.8
F1—C7—C8	117.58 (12)	C3'—C2'—H4'	119.8
C9—C8—N2	123.46 (13)	O3'—C3'—C2'	117.71 (13)
C9—C8—C7	117.17 (13)	O3'—C3'—C4'	122.36 (13)
N2—C8—C7	119.31 (12)	C2'—C3'—C4'	119.93 (13)
N2—C14—C13	109.32 (12)	C5'—C4'—C3'	119.66 (13)
N2—C14—H2'	109.8	C5'—C4'—H7'	120.2
C13—C14—H2'	109.8	C3'—C4'—H7'	120.2
N2—C14—H1'	109.8	C6'—C5'—C4'	120.37 (14)
C13—C14—H1'	109.8	C6'—C5'—H6'	119.8
H2'—C14—H1'	108.3	C4'—C5'—H6'	119.8
N3—C13—C14	110.38 (12)	C5'—C6'—C1'	120.30 (14)
N3—C13—H17	109.6	C5'—C6'—H5'	119.9
C14—C13—H17	109.6	C1'—C6'—H5'	119.9
C13—N3—C12—C11	56.71 (15)	C15—N1—C10—C5	179.56 (12)
O1—C3—C2—C1	−4.8 (3)	C6—C5—C10—N1	−176.72 (13)
O2—C3—C2—C1	175.03 (15)	C4—C5—C10—N1	5.2 (2)
O1—C3—C2—C4	178.68 (17)	C6—C5—C10—C9	5.0 (2)
O2—C3—C2—C4	−1.5 (2)	C4—C5—C10—C9	−173.08 (13)
C1—C2—C4—O3	−175.59 (14)	C10—N1—C1—C2	−4.0 (2)
C3—C2—C4—O3	0.8 (2)	C15—N1—C1—C2	176.99 (14)
C1—C2—C4—C5	4.2 (2)	C4—C2—C1—N1	1.5 (2)
C3—C2—C4—C5	−179.43 (14)	C3—C2—C1—N1	−175.11 (14)
O3—C4—C5—C10	172.34 (13)	C1—N1—C15—C16	104.83 (15)
C2—C4—C5—C10	−7.4 (2)	C10—N1—C15—C16	−74.17 (16)
O3—C4—C5—C6	−5.7 (2)	N2—C8—C9—C10	−178.18 (13)
C2—C4—C5—C6	174.56 (13)	C7—C8—C9—C10	−1.1 (2)
C10—C5—C6—C7	−2.6 (2)	N1—C10—C9—C8	178.59 (13)
C4—C5—C6—C7	175.46 (13)	C5—C10—C9—C8	−3.1 (2)
C5—C6—C7—F1	177.00 (12)	C8—N2—C11—C12	−165.92 (12)
C5—C6—C7—C8	−1.7 (2)	C14—N2—C11—C12	59.95 (15)
C14—N2—C8—C9	11.58 (19)	N3—C12—C11—N2	−57.74 (15)
C11—N2—C8—C9	−119.75 (15)	O2'—C7'—C1'—C2'	−20.0 (2)
C14—N2—C8—C7	−165.48 (13)	O1'—C7'—C1'—C2'	160.21 (13)
C11—N2—C8—C7	63.19 (17)	O2'—C7'—C1'—C6'	161.42 (13)
C6—C7—C8—C9	3.5 (2)	O1'—C7'—C1'—C6'	−18.4 (2)
F1—C7—C8—C9	−175.15 (12)	C6'—C1'—C2'—C3'	1.6 (2)
C6—C7—C8—N2	−179.21 (13)	C7'—C1'—C2'—C3'	−177.04 (13)
F1—C7—C8—N2	2.10 (19)	C1'—C2'—C3'—O3'	178.50 (13)
C8—N2—C14—C13	166.68 (12)	C1'—C2'—C3'—C4'	−2.1 (2)
C11—N2—C14—C13	−59.99 (15)	O3'—C3'—C4'—C5'	−179.89 (13)
C12—N3—C13—C14	−57.83 (16)	C2'—C3'—C4'—C5'	0.8 (2)
N2—C14—C13—N3	58.93 (16)	C3'—C4'—C5'—C6'	1.1 (2)
C1—N1—C10—C9	178.87 (13)	C4'—C5'—C6'—C1'	−1.7 (2)
C15—N1—C10—C9	−2.1 (2)	C2'—C1'—C6'—C5'	0.4 (2)
C1—N1—C10—C5	0.6 (2)	C7'—C1'—C6'—C5'	178.97 (13)

(2013130_0m)

Crystal data

C21H30FN3O10S	V = 1155.6 (5) Å^3
Mr = 535.55	Z = 2
Triclinic, P1	F(000) = 564.0
a = 9.041 (3) Å	Dx = 1.539 Mg m^−3
b = 10.767 (3) Å	Mo Kα radiation, λ = 0.71073 Å
c = 12.438 (3) Å	µ = 0.21 mm^−1
α = 89.118 (19)°	T = 100 K
β = 81.880 (17)°	Sheet, colorless
γ = 74.64 (2)°	0.21 × 0.15 × 0.13 mm

Data collection

CCD area detector diffractometer	2459 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.101
Graphite monochromator	θmax = 25.0°, θmin = 1.7°
phi and ω scans	h = −10→10
15891 measured reflections	k = −12→12
4065 independent reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.075	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.P)^2 + 0.5688P] where P = (Fo^2 + 2Fc^2)/3
4065 reflections	(Δ/σ)max < 0.001
334 parameters	Δρmax = 0.41 e Å^−3
22 restraints	Δρmin = −0.41 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1'	0.6998 (2)	0.00961 (19)	0.80804 (15)	0.0173 (5)
S1	0.78173 (9)	0.11106 (8)	0.79393 (6)	0.0144 (2)
F1	−0.36051 (18)	0.45642 (16)	0.13590 (12)	0.0165 (4)
O1S	0.3659 (2)	0.57997 (19)	0.32050 (15)	0.0199 (5)
H1A	0.3302	0.6133	0.2687	0.030*
H1B	0.4513	0.5975	0.3234	0.030*
O4S	0.6974 (2)	0.01821 (19)	0.45137 (16)	0.0250 (6)
H4B	0.6200	0.0198	0.4127	0.038*
H4A	0.6776	−0.0148	0.5102	0.038*
O1	0.3801 (2)	0.3448 (2)	−0.36931 (16)	0.0207 (5)
N3	−0.2310 (3)	0.2514 (3)	0.4917 (2)	0.0167 (7)
O2	0.1325 (2)	0.40459 (19)	−0.39447 (15)	0.0189 (5)
H1	0.0475	0.4118	−0.3581	0.028*
O3	−0.0763 (2)	0.43031 (19)	−0.24066 (15)	0.0166 (5)
O3'	0.8437 (2)	0.12433 (19)	0.68129 (15)	0.0166 (5)
O2'	0.6884 (2)	0.23205 (19)	0.84730 (15)	0.0163 (5)
C3	0.2410 (4)	0.3633 (3)	−0.3335 (2)	0.0164 (7)
C2	0.1857 (3)	0.3414 (3)	−0.2191 (2)	0.0116 (7)
C4	0.0253 (4)	0.3795 (3)	−0.1784 (2)	0.0130 (7)
C5	−0.0191 (3)	0.3617 (3)	−0.0657 (2)	0.0106 (7)
C6	−0.1745 (3)	0.4073 (3)	−0.0164 (2)	0.0122 (8)
H9	−0.2512	0.4451	−0.0583	0.015*
C7	−0.2115 (3)	0.3960 (3)	0.0913 (2)	0.0112 (7)
C8	−0.1063 (4)	0.3290 (3)	0.1600 (2)	0.0112 (7)
C14	−0.0290 (3)	0.2480 (3)	0.3339 (2)	0.0154 (8)
H18	0.0660	0.2729	0.3110	0.019*
H19	−0.0084	0.1564	0.3192	0.019*
C13	−0.0766 (3)	0.2745 (3)	0.4540 (2)	0.0182 (8)
H16	0.0004	0.2193	0.4930	0.022*
H17	−0.0807	0.3632	0.4703	0.022*
C11	−0.3004 (3)	0.2924 (3)	0.3099 (2)	0.0152 (8)
H11	−0.2919	0.2015	0.2995	0.018*
H10	−0.3781	0.3410	0.2679	0.018*
C12	−0.3499 (3)	0.3293 (3)	0.4284 (2)	0.0160 (8)
H13	−0.3598	0.4203	0.4392	0.019*
H12	−0.4496	0.3131	0.4528	0.019*
C10	0.0917 (3)	0.3018 (3)	0.0005 (2)	0.0122 (7)
C9	0.0478 (3)	0.2815 (3)	0.1100 (2)	0.0116 (7)
H8	0.1221	0.2357	0.1507	0.014*
N1	0.2482 (3)	0.2619 (2)	−0.04663 (19)	0.0110 (6)
C1	0.2894 (4)	0.2845 (3)	−0.1512 (2)	0.0128 (8)
H2	0.3941	0.2601	−0.1792	0.015*
C3'	0.9470 (3)	0.0563 (3)	0.8637 (2)	0.0101 (7)
C2'	0.9315 (3)	0.0256 (3)	0.9761 (2)	0.0105 (7)
C4'	1.0910 (3)	0.0414 (3)	0.8043 (2)	0.0132 (8)
H4'	1.0994	0.0641	0.7317	0.016*
C5'	1.2258 (4)	−0.0081 (3)	0.8525 (2)	0.0152 (8)
H5'	1.3228	−0.0176	0.8118	0.018*
C1'	0.7855 (3)	0.0421 (3)	1.0410 (2)	0.0145 (8)
H1'	0.6956	0.0768	1.0106	0.017*
O3S	0.4143 (2)	0.0952 (2)	0.35731 (15)	0.0240 (6)
H3B	0.3684	0.1716	0.3609	0.036*
H3A	0.3828	0.0619	0.3051	0.036*
N2	−0.1494 (3)	0.3186 (2)	0.27087 (18)	0.0119 (6)
O2S	0.2716 (2)	0.35555 (19)	0.38184 (15)	0.0211 (6)
H2A	0.2358	0.3723	0.4528	0.032*
H2B	0.3046	0.4159	0.3567	0.032*
C15	0.3703 (3)	0.1960 (3)	0.0180 (2)	0.0142 (8)
H3	0.4600	0.1482	−0.0308	0.017*
H4	0.3325	0.1348	0.0647	0.017*
C16	0.4194 (3)	0.2887 (3)	0.0875 (2)	0.0188 (8)
H7	0.4662	0.3443	0.0413	0.028*
H6	0.4928	0.2408	0.1317	0.028*
H5	0.3301	0.3396	0.1333	0.028*
H14	−0.257 (3)	0.274 (3)	0.5600 (7)	0.032 (11)*
H15	−0.238 (4)	0.162 (3)	0.487 (3)	0.057 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1'	0.0207 (12)	0.0185 (12)	0.0179 (12)	−0.0105 (9)	−0.0102 (10)	0.0023 (9)
S1	0.0150 (5)	0.0159 (5)	0.0137 (5)	−0.0049 (4)	−0.0055 (4)	0.0011 (4)
F1	0.0093 (10)	0.0216 (11)	0.0165 (10)	−0.0015 (8)	0.0002 (8)	−0.0019 (8)
O1S	0.0171 (13)	0.0242 (14)	0.0198 (13)	−0.0055 (11)	−0.0080 (10)	0.0040 (10)
O4S	0.0266 (14)	0.0315 (15)	0.0212 (14)	−0.0145 (12)	−0.0044 (11)	0.0035 (11)
O1	0.0190 (11)	0.0300 (14)	0.0149 (13)	−0.0111 (12)	0.0004 (10)	0.0004 (10)
N3	0.0154 (17)	0.024 (2)	0.0123 (18)	−0.0065 (14)	−0.0035 (14)	0.0014 (14)
O2	0.0134 (13)	0.0323 (15)	0.0135 (13)	−0.0107 (11)	−0.0013 (10)	0.0035 (10)
O3	0.0141 (12)	0.0211 (13)	0.0164 (12)	−0.0056 (10)	−0.0063 (9)	0.0019 (9)
O3'	0.0169 (13)	0.0236 (14)	0.0084 (12)	−0.0035 (10)	−0.0033 (10)	0.0050 (10)
O2'	0.0126 (12)	0.0157 (13)	0.0185 (13)	0.0006 (10)	−0.0033 (10)	−0.0028 (10)
C3	0.0192 (13)	0.0178 (18)	0.0151 (18)	−0.0098 (16)	−0.0028 (15)	−0.0028 (14)
C2	0.0124 (19)	0.0116 (19)	0.0123 (19)	−0.0059 (15)	−0.0010 (15)	−0.0017 (14)
C4	0.0152 (17)	0.0130 (18)	0.0146 (18)	−0.0081 (13)	−0.0061 (12)	−0.0012 (13)
C5	0.0105 (18)	0.0095 (19)	0.0122 (18)	−0.0016 (14)	−0.0043 (15)	−0.0003 (14)
C6	0.0134 (19)	0.0114 (19)	0.0143 (19)	−0.0046 (15)	−0.0074 (15)	−0.0006 (14)
C7	0.0044 (18)	0.0101 (19)	0.018 (2)	−0.0013 (14)	0.0002 (15)	−0.0045 (14)
C8	0.0155 (19)	0.0096 (19)	0.0111 (19)	−0.0065 (15)	−0.0042 (15)	−0.0030 (14)
C14	0.0125 (18)	0.020 (2)	0.0138 (19)	−0.0032 (16)	−0.0052 (15)	0.0003 (15)
C13	0.016 (2)	0.027 (2)	0.0131 (19)	−0.0091 (16)	−0.0027 (15)	0.0008 (15)
C11	0.0140 (19)	0.021 (2)	0.0130 (19)	−0.0077 (16)	−0.0033 (15)	0.0007 (14)
C12	0.0110 (18)	0.024 (2)	0.0127 (19)	−0.0037 (16)	−0.0023 (15)	0.0014 (15)
C10	0.0105 (19)	0.0112 (19)	0.0146 (19)	−0.0026 (15)	−0.0010 (15)	−0.0037 (14)
C9	0.0141 (19)	0.0084 (19)	0.0139 (19)	−0.0041 (15)	−0.0050 (15)	−0.0012 (14)
N1	0.0093 (15)	0.0134 (16)	0.0102 (15)	−0.0015 (12)	−0.0043 (12)	0.0022 (12)
C1	0.0117 (18)	0.0129 (19)	0.0138 (19)	−0.0046 (15)	0.0008 (15)	−0.0041 (14)
C3'	0.0109 (18)	0.0088 (18)	0.0113 (18)	−0.0023 (14)	−0.0045 (15)	−0.0032 (14)
C2'	0.0106 (18)	0.0076 (18)	0.0135 (19)	−0.0033 (14)	0.0001 (14)	−0.0041 (13)
C4'	0.018 (2)	0.0129 (19)	0.0098 (18)	−0.0050 (15)	−0.0028 (15)	−0.0014 (14)
C5'	0.0138 (19)	0.017 (2)	0.015 (2)	−0.0052 (15)	−0.0019 (16)	−0.0028 (15)
C1'	0.0118 (19)	0.014 (2)	0.018 (2)	−0.0009 (15)	−0.0087 (16)	−0.0035 (15)
O3S	0.0285 (14)	0.0231 (14)	0.0231 (14)	−0.0074 (11)	−0.0113 (11)	−0.0020 (11)
N2	0.0066 (14)	0.0228 (17)	0.0080 (15)	−0.0071 (12)	−0.0002 (12)	0.0017 (12)
O2S	0.0267 (14)	0.0241 (14)	0.0149 (13)	−0.0113 (11)	−0.0018 (11)	0.0009 (10)
C15	0.0082 (18)	0.020 (2)	0.0122 (18)	0.0002 (15)	−0.0023 (14)	0.0023 (14)
C16	0.016 (2)	0.022 (2)	0.020 (2)	−0.0043 (16)	−0.0081 (15)	−0.0010 (15)

Geometric parameters (Å, º)

O1'—S1	1.470 (2)	C8—N2	1.390 (3)
S1—O3'	1.453 (2)	C8—C9	1.407 (4)
S1—O2'	1.461 (2)	C14—N2	1.470 (3)
S1—C3'	1.794 (3)	C14—C13	1.505 (4)
F1—C7	1.371 (3)	C11—N2	1.481 (4)
O1—C3	1.238 (3)	C11—C12	1.506 (4)
N3—C12	1.491 (4)	C10—C9	1.394 (4)
N3—C13	1.492 (4)	C10—N1	1.408 (4)
O2—C3	1.305 (3)	N1—C1	1.337 (3)
O3—C4	1.290 (3)	N1—C15	1.478 (3)
C3—C2	1.477 (4)	C3'—C4'	1.374 (4)
C2—C1	1.369 (4)	C3'—C2'	1.427 (4)
C2—C4	1.418 (4)	C2'—C1'	1.416 (4)
C4—C5	1.427 (4)	C2'—C2'^i	1.425 (5)
C5—C10	1.404 (4)	C4'—C5'	1.408 (4)
C5—C6	1.411 (4)	C5'—C1'^i	1.365 (4)
C6—C7	1.346 (4)	C1'—C5'^i	1.365 (4)
C7—C8	1.416 (4)	C15—C16	1.520 (4)
O3'—S1—O2'	113.96 (12)	N2—C14—C13	111.8 (2)
O3'—S1—O1'	112.66 (12)	N3—C13—C14	111.6 (2)
O2'—S1—O1'	111.61 (12)	N2—C11—C12	110.6 (2)
O3'—S1—C3'	105.74 (13)	N3—C12—C11	108.7 (2)
O2'—S1—C3'	106.78 (12)	C9—C10—C5	120.9 (3)
O1'—S1—C3'	105.34 (13)	C9—C10—N1	120.8 (3)
C12—N3—C13	110.4 (3)	C5—C10—N1	118.3 (3)
O1—C3—O2	122.1 (3)	C10—C9—C8	121.4 (3)
O1—C3—C2	122.6 (3)	C1—N1—C10	120.2 (2)
O2—C3—C2	115.3 (3)	C1—N1—C15	118.7 (2)
C1—C2—C4	119.3 (3)	C10—N1—C15	121.1 (2)
C1—C2—C3	120.1 (3)	N1—C1—C2	123.5 (3)
C4—C2—C3	120.6 (3)	C4'—C3'—C2'	120.6 (3)
O3—C4—C2	121.1 (3)	C4'—C3'—S1	117.5 (2)
O3—C4—C5	121.3 (3)	C2'—C3'—S1	121.8 (2)
C2—C4—C5	117.5 (3)	C1'—C2'—C2'^i	118.9 (3)
C10—C5—C6	117.9 (3)	C1'—C2'—C3'	122.6 (3)
C10—C5—C4	120.9 (3)	C2'^i—C2'—C3'	118.5 (3)
C6—C5—C4	121.2 (3)	C3'—C4'—C5'	120.5 (3)
C7—C6—C5	119.9 (3)	C1'^i—C5'—C4'	120.2 (3)
C6—C7—F1	116.8 (3)	C5'^i—C1'—C2'	121.3 (3)
C6—C7—C8	124.2 (3)	C8—N2—C14	117.4 (2)
F1—C7—C8	119.0 (3)	C8—N2—C11	119.2 (2)
N2—C8—C9	122.0 (3)	C14—N2—C11	111.1 (2)
N2—C8—C7	122.5 (3)	N1—C15—C16	112.8 (2)
C9—C8—C7	115.3 (3)
O1—C3—C2—C1	−7.9 (5)	C5—C10—N1—C1	1.9 (4)
O2—C3—C2—C1	172.6 (3)	C9—C10—N1—C15	0.8 (4)
O1—C3—C2—C4	171.8 (3)	C5—C10—N1—C15	−178.8 (3)
O2—C3—C2—C4	−7.7 (4)	C10—N1—C1—C2	−2.5 (4)
C1—C2—C4—O3	−178.1 (3)	C15—N1—C1—C2	178.1 (3)
C3—C2—C4—O3	2.2 (4)	C4—C2—C1—N1	0.0 (4)
C1—C2—C4—C5	3.0 (4)	C3—C2—C1—N1	179.7 (3)
C3—C2—C4—C5	−176.8 (3)	O3'—S1—C3'—C4'	1.7 (3)
O3—C4—C5—C10	177.5 (3)	O2'—S1—C3'—C4'	−120.0 (2)
C2—C4—C5—C10	−3.5 (4)	O1'—S1—C3'—C4'	121.2 (2)
O3—C4—C5—C6	−4.7 (4)	O3'—S1—C3'—C2'	−176.6 (2)
C2—C4—C5—C6	174.3 (3)	O2'—S1—C3'—C2'	61.7 (3)
C10—C5—C6—C7	1.9 (4)	O1'—S1—C3'—C2'	−57.0 (3)
C4—C5—C6—C7	−176.0 (3)	C4'—C3'—C2'—C1'	178.6 (3)
C5—C6—C7—F1	172.1 (2)	S1—C3'—C2'—C1'	−3.2 (4)
C5—C6—C7—C8	−6.4 (5)	C4'—C3'—C2'—C2'^i	−2.4 (5)
C6—C7—C8—N2	−179.5 (3)	S1—C3'—C2'—C2'^i	175.8 (3)
F1—C7—C8—N2	2.0 (4)	C2'—C3'—C4'—C5'	1.8 (4)
C6—C7—C8—C9	5.0 (4)	S1—C3'—C4'—C5'	−176.5 (2)
F1—C7—C8—C9	−173.5 (2)	C3'—C4'—C5'—C1'^i	0.2 (4)
C12—N3—C13—C14	−55.6 (3)	C2'^i—C2'—C1'—C5'^i	−1.1 (5)
N2—C14—C13—N3	52.8 (3)	C3'—C2'—C1'—C5'^i	177.9 (3)
C13—N3—C12—C11	59.0 (3)	C9—C8—N2—C14	−3.9 (4)
N2—C11—C12—N3	−60.6 (3)	C7—C8—N2—C14	−179.2 (3)
C6—C5—C10—C9	3.7 (4)	C9—C8—N2—C11	−142.8 (3)
C4—C5—C10—C9	−178.4 (3)	C7—C8—N2—C11	42.0 (4)
C6—C5—C10—N1	−176.7 (3)	C13—C14—N2—C8	164.2 (3)
C4—C5—C10—N1	1.1 (4)	C13—C14—N2—C11	−53.9 (3)
C5—C10—C9—C8	−5.1 (4)	C12—C11—N2—C8	−160.5 (3)
N1—C10—C9—C8	175.4 (3)	C12—C11—N2—C14	58.3 (3)
N2—C8—C9—C10	−174.7 (3)	C1—N1—C15—C16	99.2 (3)
C7—C8—C9—C10	0.9 (4)	C10—N1—C15—C16	−80.1 (3)
C9—C10—N1—C1	−178.5 (3)

Symmetry code: (i) −x+2, −y, −z+2.

(2013176_0ma)

Crystal data

C26H23FN3O10S	F(000) = 2440
Mr = 588.54	Dx = 1.462 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
a = 11.6515 (3) Å	µ = 0.19 mm^−1
b = 7.4209 (2) Å	T = 100 K
c = 61.8325 (18) Å	Sheet, colourless
V = 5346.3 (3) Å^3	0.30 × 0.04 × 0.03 mm
Z = 8

Data collection

CCD area detector diffractometer	5987 independent reflections
Radiation source: fine-focus sealed tube	3739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.103
phi and ω scans	θmax = 27.5°, θmin = 0.7°
Absorption correction: empirical (using intensity measurements) SADABS	h = −12→14
Tmin = 0.948, Tmax = 0.995	k = −9→9
47387 measured reflections	l = −80→73

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.051P)^2 + 7.5635P] where P = (Fo^2 + 2Fc^2)/3
5987 reflections	(Δ/σ)max < 0.001
419 parameters	Δρmax = 0.43 e Å^−3
4 restraints	Δρmin = −0.40 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1'	0.48089 (7)	0.27147 (11)	0.179103 (13)	0.0196 (2)
F1	0.35001 (17)	0.3205 (3)	0.11186 (3)	0.0286 (5)
O3'	0.5662 (2)	0.4165 (3)	0.18138 (4)	0.0252 (6)
O2'	0.5345 (2)	0.1008 (3)	0.17323 (4)	0.0256 (6)
C7	0.1635 (3)	0.3845 (4)	0.09842 (5)	0.0204 (8)
O1'	0.3868 (2)	0.3218 (3)	0.16499 (4)	0.0280 (6)
C1'	0.4770 (3)	0.2951 (4)	0.22329 (5)	0.0164 (7)
H1'	0.5476	0.3527	0.2221	0.020*
C4'	0.2631 (3)	0.1236 (4)	0.22610 (5)	0.0196 (7)
H4'	0.1919	0.0673	0.2268	0.023*
C5'	0.3179 (3)	0.1803 (4)	0.24543 (5)	0.0169 (7)
C3'	0.3139 (3)	0.1506 (4)	0.20635 (5)	0.0196 (8)
H3'	0.2778	0.1110	0.1938	0.024*
C10'	0.4272 (3)	0.2656 (4)	0.24409 (5)	0.0146 (7)
C6'	0.2675 (3)	0.1530 (4)	0.26612 (5)	0.0200 (7)
H6'	0.1962	0.0975	0.2672	0.024*
C8'	0.4314 (3)	0.2900 (4)	0.28304 (5)	0.0219 (8)
H8'	0.4687	0.3258	0.2956	0.026*
C2'	0.4214 (3)	0.2390 (4)	0.20519 (5)	0.0169 (7)
N2	0.1157 (3)	0.3076 (4)	0.11711 (4)	0.0213 (6)
N3	−0.0025 (3)	0.2150 (4)	0.15587 (5)	0.0301 (8)
C9'	0.4824 (3)	0.3179 (4)	0.26351 (5)	0.0183 (7)
H9'	0.5543	0.3720	0.2629	0.022*
C7'	0.3230 (3)	0.2076 (4)	0.28433 (5)	0.0225 (8)
H7'	0.2889	0.1902	0.2978	0.027*
C9	0.3348 (3)	0.4535 (5)	0.07762 (5)	0.0241 (8)
H9	0.4145	0.4553	0.0767	0.029*
C5	0.1493 (3)	0.5138 (5)	0.06240 (5)	0.0239 (8)
O1	0.4300 (3)	0.5791 (4)	0.03843 (4)	0.0468 (8)
N1	0.0811 (3)	0.5803 (4)	0.04557 (5)	0.0334 (8)
C8	0.2835 (3)	0.3896 (5)	0.09580 (5)	0.0222 (8)
C14	−0.0070 (3)	0.2688 (5)	0.11660 (6)	0.0285 (9)
H14A	−0.0275	0.2171	0.1027	0.034*
H14B	−0.0502	0.3794	0.1185	0.034*
C1	0.3225 (4)	0.5815 (5)	0.04072 (6)	0.0300 (9)
O2	0.4042 (3)	0.7186 (4)	0.00143 (4)	0.0530 (9)
H2	0.4335	0.6732	0.0122	0.080*
C6	0.0972 (3)	0.4487 (4)	0.08137 (5)	0.0244 (8)
H6	0.0176	0.4486	0.0825	0.029*
C12	0.1201 (3)	0.2678 (5)	0.15635 (5)	0.0254 (8)
H12A	0.1677	0.1607	0.1555	0.031*
H12B	0.1369	0.3279	0.1699	0.031*
O3	0.2300 (3)	0.7879 (5)	−0.00994 (4)	0.0551 (9)
C10	0.2685 (3)	0.5164 (5)	0.06037 (5)	0.0241 (8)
C13	−0.0360 (3)	0.1380 (5)	0.13452 (5)	0.0292 (9)
H13A	−0.1178	0.1133	0.1344	0.035*
H13B	0.0043	0.0253	0.1322	0.035*
C2	0.2474 (4)	0.6479 (5)	0.02445 (5)	0.0294 (9)
C11	0.1482 (4)	0.3922 (4)	0.13774 (5)	0.0276 (9)
H11A	0.1070	0.5049	0.1395	0.033*
H11B	0.2297	0.4184	0.1377	0.033*
C4	0.1317 (4)	0.6449 (5)	0.02762 (6)	0.0325 (10)
H4	0.0849	0.6903	0.0167	0.039*
C3	0.2915 (4)	0.7227 (6)	0.00377 (6)	0.0396 (11)
C15	−0.0474 (4)	0.5874 (8)	0.04713 (7)	0.0520 (14)
O2S	0.8206 (11)	0.768 (3)	0.11484 (18)	0.120 (6)	0.61 (4)
O4S	0.6648 (6)	0.5048 (11)	0.04821 (10)	0.051 (3)	0.467 (10)
O4S'	0.6546 (6)	0.6739 (12)	0.05658 (12)	0.081 (3)	0.533 (10)
O3S	0.722 (2)	0.055 (2)	0.0921 (2)	0.073 (8)	0.42 (5)
C16	−0.0964 (8)	0.4282 (13)	0.04290 (15)	0.048 (2)	0.50
C16'	−0.0946 (8)	0.7322 (18)	0.05749 (16)	0.066 (3)	0.50
O3S'	0.788 (4)	0.016 (5)	0.0925 (2)	0.182 (11)	0.58 (5)
O1S	0.7765 (2)	0.4094 (4)	0.15897 (4)	0.0376 (7)
H1B	0.7144	0.4237	0.1649	0.056*
H1A	0.8095	0.5100	0.1634	0.056*
H101	−0.018 (4)	0.133 (5)	0.1655 (6)	0.074 (17)*
H100	−0.042 (3)	0.313 (4)	0.1587 (6)	0.040 (12)*
O2S'	0.790 (4)	0.858 (9)	0.1162 (6)	0.31 (3)	0.39 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1'	0.0206 (5)	0.0208 (4)	0.0175 (4)	−0.0030 (3)	−0.0005 (4)	0.0032 (3)
F1	0.0293 (13)	0.0356 (12)	0.0209 (11)	−0.0010 (9)	−0.0053 (9)	0.0062 (8)
O3'	0.0259 (14)	0.0293 (13)	0.0203 (12)	−0.0099 (11)	0.0008 (11)	0.0043 (10)
O2'	0.0279 (15)	0.0272 (13)	0.0217 (13)	0.0011 (11)	0.0044 (11)	0.0003 (10)
C7	0.028 (2)	0.0191 (16)	0.0138 (16)	−0.0040 (15)	0.0009 (15)	−0.0010 (13)
O1'	0.0255 (15)	0.0358 (14)	0.0226 (13)	−0.0020 (11)	−0.0068 (11)	0.0094 (11)
C1'	0.0100 (17)	0.0171 (15)	0.0219 (17)	−0.0002 (13)	−0.0007 (14)	0.0035 (12)
C4'	0.0129 (19)	0.0164 (16)	0.0294 (19)	−0.0008 (13)	0.0005 (15)	0.0046 (13)
C5'	0.0149 (18)	0.0111 (15)	0.0248 (18)	0.0024 (13)	−0.0011 (15)	0.0006 (12)
C3'	0.023 (2)	0.0169 (16)	0.0189 (18)	−0.0007 (14)	−0.0046 (15)	0.0020 (12)
C10'	0.0146 (18)	0.0094 (14)	0.0198 (16)	0.0026 (13)	0.0000 (13)	−0.0005 (12)
C6'	0.017 (2)	0.0152 (16)	0.0279 (19)	0.0014 (13)	0.0049 (16)	0.0026 (13)
C8'	0.027 (2)	0.0206 (17)	0.0182 (18)	−0.0002 (15)	−0.0028 (15)	−0.0008 (13)
C2'	0.0132 (18)	0.0166 (15)	0.0208 (17)	0.0011 (13)	−0.0007 (14)	0.0048 (13)
N2	0.0257 (18)	0.0252 (15)	0.0131 (14)	−0.0035 (13)	0.0007 (12)	0.0017 (11)
N3	0.040 (2)	0.0278 (17)	0.0229 (17)	0.0133 (15)	0.0103 (15)	0.0089 (13)
C9'	0.0145 (18)	0.0132 (15)	0.0271 (18)	0.0000 (13)	−0.0014 (15)	0.0020 (12)
C7'	0.026 (2)	0.0198 (17)	0.0218 (18)	0.0041 (15)	0.0050 (15)	0.0031 (13)
C9	0.024 (2)	0.0290 (19)	0.0188 (18)	−0.0047 (16)	0.0044 (16)	−0.0010 (14)
C5	0.033 (2)	0.0246 (18)	0.0140 (17)	−0.0026 (15)	−0.0047 (16)	0.0014 (13)
O1	0.0344 (19)	0.073 (2)	0.0326 (16)	−0.0078 (16)	0.0090 (14)	0.0164 (15)
N1	0.037 (2)	0.044 (2)	0.0193 (16)	−0.0025 (16)	−0.0009 (15)	0.0095 (14)
C8	0.028 (2)	0.0240 (18)	0.0146 (17)	−0.0017 (15)	−0.0050 (15)	−0.0003 (13)
C14	0.028 (2)	0.037 (2)	0.0206 (18)	0.0008 (17)	0.0061 (16)	0.0078 (15)
C1	0.038 (3)	0.032 (2)	0.0200 (19)	−0.0062 (18)	0.0027 (18)	0.0004 (15)
O2	0.055 (2)	0.074 (2)	0.0296 (16)	−0.0059 (18)	0.0098 (15)	0.0195 (15)
C6	0.027 (2)	0.0266 (18)	0.0197 (18)	−0.0045 (15)	−0.0015 (16)	0.0019 (14)
C12	0.041 (2)	0.0208 (17)	0.0144 (17)	0.0015 (16)	0.0022 (15)	0.0007 (13)
O3	0.069 (2)	0.071 (2)	0.0254 (16)	0.0153 (18)	0.0114 (16)	0.0220 (15)
C10	0.034 (2)	0.0237 (18)	0.0146 (17)	−0.0056 (16)	0.0032 (16)	0.0005 (13)
C13	0.026 (2)	0.039 (2)	0.0225 (19)	−0.0008 (17)	0.0067 (17)	0.0071 (16)
C2	0.044 (3)	0.0283 (19)	0.0157 (18)	−0.0016 (18)	0.0019 (18)	0.0030 (14)
C11	0.049 (3)	0.0199 (17)	0.0136 (17)	0.0003 (16)	0.0023 (17)	0.0012 (13)
C4	0.051 (3)	0.032 (2)	0.0155 (18)	0.0009 (19)	−0.0041 (18)	0.0044 (15)
C3	0.057 (3)	0.039 (2)	0.023 (2)	−0.001 (2)	0.008 (2)	0.0054 (17)
C15	0.028 (3)	0.093 (4)	0.035 (3)	−0.003 (3)	−0.008 (2)	0.023 (3)
O2S	0.093 (7)	0.214 (14)	0.054 (6)	−0.006 (9)	0.023 (5)	0.038 (8)
O4S	0.043 (5)	0.067 (6)	0.042 (4)	−0.007 (4)	−0.013 (3)	0.014 (4)
O4S'	0.075 (5)	0.097 (8)	0.070 (5)	0.026 (5)	0.015 (4)	0.034 (5)
O3S	0.041 (11)	0.138 (15)	0.039 (6)	0.001 (7)	0.004 (6)	−0.007 (6)
C16	0.033 (6)	0.061 (6)	0.050 (6)	0.002 (5)	−0.005 (4)	−0.004 (5)
C16'	0.024 (6)	0.133 (11)	0.039 (6)	0.009 (6)	−0.002 (4)	−0.003 (6)
O3S'	0.13 (3)	0.37 (2)	0.052 (7)	−0.08 (2)	0.002 (9)	−0.053 (10)
O1S	0.0274 (17)	0.0457 (17)	0.0396 (16)	0.0089 (13)	−0.0001 (13)	−0.0081 (13)
O2S'	0.17 (3)	0.45 (6)	0.31 (4)	−0.19 (3)	0.10 (3)	−0.27 (5)

Geometric parameters (Å, º)

S1'—O1'	1.450 (2)	N3—C12	1.481 (5)
S1'—O2'	1.458 (2)	N3—C13	1.491 (5)
S1'—O3'	1.471 (2)	C9—C8	1.358 (5)
S1'—C2'	1.772 (3)	C9—C10	1.398 (5)
F1—C8	1.360 (4)	C5—C10	1.395 (5)
C7—C6	1.391 (5)	C5—N1	1.399 (4)
C7—N2	1.404 (4)	C5—C6	1.406 (5)
C7—C8	1.409 (5)	O1—C1	1.260 (5)
C1'—C2'	1.358 (4)	N1—C4	1.345 (4)
C1'—C10'	1.428 (4)	N1—C15	1.501 (5)
C4'—C3'	1.371 (4)	C14—C13	1.512 (5)
C4'—C5'	1.419 (4)	C1—C2	1.422 (5)
C5'—C6'	1.422 (5)	C1—C10	1.452 (5)
C5'—C10'	1.424 (4)	O2—C3	1.321 (5)
C3'—C2'	1.416 (4)	C12—C11	1.511 (4)
C10'—C9'	1.416 (4)	O3—C3	1.211 (5)
C6'—C7'	1.360 (5)	C2—C4	1.362 (6)
C8'—C9'	1.362 (5)	C2—C3	1.486 (5)
C8'—C7'	1.406 (5)	C15—C16	1.338 (10)
N2—C14	1.459 (5)	C15—C16'	1.367 (12)
N2—C11	1.471 (4)
O1'—S1'—O2'	113.45 (15)	C10—C5—N1	119.6 (3)
O1'—S1'—O3'	112.31 (14)	C10—C5—C6	120.6 (3)
O2'—S1'—O3'	111.68 (14)	N1—C5—C6	119.8 (3)
O1'—S1'—C2'	106.68 (15)	C4—N1—C5	119.4 (3)
O2'—S1'—C2'	106.03 (14)	C4—N1—C15	118.5 (3)
O3'—S1'—C2'	106.05 (14)	C5—N1—C15	122.1 (3)
C6—C7—N2	122.9 (3)	C9—C8—F1	119.0 (3)
C6—C7—C8	117.1 (3)	C9—C8—C7	122.8 (3)
N2—C7—C8	119.9 (3)	F1—C8—C7	118.1 (3)
C2'—C1'—C10'	120.1 (3)	N2—C14—C13	109.3 (3)
C3'—C4'—C5'	120.9 (3)	O1—C1—C2	122.5 (3)
C4'—C5'—C6'	122.0 (3)	O1—C1—C10	121.4 (3)
C4'—C5'—C10'	119.0 (3)	C2—C1—C10	116.1 (4)
C6'—C5'—C10'	119.0 (3)	C7—C6—C5	120.7 (3)
C4'—C3'—C2'	119.6 (3)	N3—C12—C11	110.8 (3)
C9'—C10'—C5'	118.6 (3)	C5—C10—C9	118.5 (3)
C9'—C10'—C1'	122.5 (3)	C5—C10—C1	120.8 (3)
C5'—C10'—C1'	118.9 (3)	C9—C10—C1	120.7 (3)
C7'—C6'—C5'	120.4 (3)	N3—C13—C14	110.1 (3)
C9'—C8'—C7'	120.5 (3)	C4—C2—C1	120.1 (3)
C1'—C2'—C3'	121.5 (3)	C4—C2—C3	118.2 (4)
C1'—C2'—S1'	121.5 (3)	C1—C2—C3	121.7 (4)
C3'—C2'—S1'	117.1 (2)	N2—C11—C12	110.1 (3)
C7—N2—C14	116.8 (3)	N1—C4—C2	123.9 (4)
C7—N2—C11	116.0 (3)	O3—C3—O2	121.4 (4)
C14—N2—C11	110.8 (3)	O3—C3—C2	123.2 (4)
C12—N3—C13	111.8 (3)	O2—C3—C2	115.5 (4)
C8'—C9'—C10'	120.8 (3)	C16—C15—C16'	127.9 (7)
C6'—C7'—C8'	120.6 (3)	C16—C15—N1	112.4 (6)
C8—C9—C10	120.3 (3)	C16'—C15—N1	117.3 (6)

(2013329_0m)

Crystal data

C23H26FN3O7	V = 1136.71 (10) Å^3
Mr = 475.47	Z = 2
Triclinic, P1	F(000) = 500.0
a = 7.0237 (4) Å	Dx = 1.389 Mg m^−3
b = 9.9645 (5) Å	Mo Kα radiation, λ = 0.71073 Å
c = 17.4655 (9) Å	µ = 0.11 mm^−1
α = 91.100 (3)°	T = 296 K
β = 97.543 (3)°	Sheet, colorless
γ = 109.906 (3)°	0.15 × 0.06 × 0.03 mm

Data collection

CCD area detector diffractometer	5221 independent reflections
Radiation source: fine-focus sealed tube	2989 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
phi and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements) SADABS	h = −9→9
Tmin = 0.984, Tmax = 0.997	k = −12→12
17531 measured reflections	l = −22→22

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0513P)^2 + 0.0507P] where P = (Fo^2 + 2Fc^2)/3
5221 reflections	(Δ/σ)max = 0.003
322 parameters	Δρmax = 0.17 e Å^−3
0 restraints	Δρmin = −0.20 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.82208 (17)	−0.33285 (9)	0.61457 (6)	0.0581 (3)
O2	0.54571 (18)	0.03225 (15)	0.27079 (7)	0.0529 (3)
H2	0.553 (3)	−0.051 (2)	0.2947 (12)	0.079*
O1S	0.2611 (3)	0.0897 (2)	0.04954 (10)	0.0715 (4)
O1	0.6433 (2)	0.26226 (14)	0.30653 (7)	0.0662 (4)
O3	0.61812 (17)	−0.13846 (12)	0.36964 (6)	0.0482 (3)
O3'	0.7482 (3)	0.28716 (17)	0.78613 (8)	0.0790 (5)
H1'	0.812 (4)	0.249 (3)	0.8283 (16)	0.118*
O2'	0.8187 (2)	0.19293 (15)	0.91645 (8)	0.0699 (4)
O1'	0.65917 (19)	0.21929 (14)	1.01326 (7)	0.0595 (4)
N1	0.78967 (19)	0.19248 (12)	0.53606 (7)	0.0349 (3)
N2	0.93994 (19)	−0.11350 (13)	0.73272 (7)	0.0383 (3)
N3	1.0486 (2)	−0.15138 (14)	0.89301 (7)	0.0438 (4)
H15	1.1361	−0.1707	0.9298	0.053*
H14	0.9486	−0.1374	0.9159	0.053*
C3	0.6252 (2)	0.1420 (2)	0.32344 (10)	0.0450 (4)
C2	0.6840 (2)	0.10546 (17)	0.40286 (9)	0.0360 (4)
C1	0.7373 (2)	0.20978 (16)	0.46120 (9)	0.0373 (4)
H1	0.7374	0.2999	0.4482	0.045*
C10	0.7977 (2)	0.05996 (15)	0.55761 (8)	0.0312 (3)
C9	0.8576 (2)	0.03828 (16)	0.63500 (9)	0.0339 (4)
H8	0.8927	0.1139	0.6723	0.041*
C8	0.8660 (2)	−0.09337 (16)	0.65762 (9)	0.0343 (4)
C11	1.0267 (3)	0.01119 (17)	0.78827 (9)	0.0446 (4)
H11	0.9169	0.0355	0.8063	0.054*
H10	1.1085	0.0923	0.7631	0.054*
C12	1.1588 (3)	−0.01935 (18)	0.85661 (9)	0.0467 (4)
H13	1.2795	−0.0292	0.8394	0.056*
H12	1.2037	0.0611	0.8949	0.056*
C4	0.6764 (2)	−0.03538 (17)	0.42026 (9)	0.0353 (4)
C5	0.7397 (2)	−0.05309 (16)	0.50056 (9)	0.0328 (4)
C6	0.7441 (2)	−0.18632 (16)	0.52364 (9)	0.0368 (4)
H9	0.7029	−0.2638	0.4872	0.044*
C7	0.8070 (2)	−0.20340 (16)	0.59774 (9)	0.0377 (4)
C14	0.8209 (3)	−0.23983 (18)	0.77048 (10)	0.0500 (5)
H18	0.7614	−0.3211	0.7328	0.060*
H19	0.7104	−0.2208	0.7912	0.060*
C13	0.9586 (3)	−0.27426 (18)	0.83510 (10)	0.0525 (5)
H16	0.8803	−0.3577	0.8596	0.063*
H17	1.0669	−0.2959	0.8142	0.063*
C15	0.8401 (3)	0.31597 (16)	0.59305 (10)	0.0441 (4)
H4	0.7944	0.2819	0.6414	0.053*
H3	0.7675	0.3787	0.5740	0.053*
C16	1.0657 (3)	0.3989 (2)	0.60746 (12)	0.0631 (6)
H7	1.1373	0.3387	0.6291	0.095*
H6	1.0920	0.4800	0.6430	0.095*
H5	1.1119	0.4312	0.5595	0.095*
C5'	0.3426 (4)	0.4400 (2)	0.87721 (14)	0.0801 (7)
H4'	0.2519	0.4762	0.8970	0.096*
C6'	0.4481 (3)	0.3696 (2)	0.92331 (12)	0.0623 (5)
H5'	0.4267	0.3576	0.9745	0.075*
C1'	0.5853 (3)	0.31638 (17)	0.89481 (10)	0.0444 (4)
C2'	0.6148 (3)	0.33448 (17)	0.81754 (11)	0.0512 (5)
C7'	0.6953 (3)	0.23853 (18)	0.94519 (11)	0.0477 (4)
C4'	0.3748 (4)	0.4556 (2)	0.80116 (14)	0.0788 (7)
H3'	0.3054	0.5035	0.7697	0.095*
C3'	0.5051 (4)	0.4027 (2)	0.77122 (12)	0.0679 (6)
H2'	0.5212	0.4121	0.7194	0.081*
H1A	0.376 (4)	0.137 (3)	0.0435 (16)	0.108 (11)*
H1B	0.243 (4)	−0.001 (3)	0.0584 (15)	0.114 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0853 (8)	0.0407 (5)	0.0530 (7)	0.0318 (5)	−0.0017 (5)	0.0053 (5)
O2	0.0554 (8)	0.0678 (9)	0.0296 (7)	0.0154 (6)	0.0015 (5)	0.0057 (6)
O1S	0.0715 (12)	0.0779 (11)	0.0821 (12)	0.0398 (10)	0.0305 (9)	0.0228 (9)
O1	0.0796 (9)	0.0619 (9)	0.0480 (8)	0.0185 (7)	−0.0085 (7)	0.0210 (7)
O3	0.0570 (7)	0.0511 (7)	0.0333 (7)	0.0174 (6)	−0.0005 (5)	−0.0047 (6)
O3'	0.1017 (12)	0.0968 (12)	0.0488 (10)	0.0430 (10)	0.0225 (8)	0.0154 (8)
O2'	0.0807 (10)	0.0890 (10)	0.0635 (10)	0.0541 (9)	0.0227 (8)	0.0231 (8)
O1'	0.0638 (9)	0.0843 (9)	0.0421 (8)	0.0404 (7)	0.0056 (6)	0.0200 (7)
N1	0.0394 (7)	0.0341 (7)	0.0302 (8)	0.0123 (6)	0.0021 (6)	0.0043 (6)
N2	0.0430 (8)	0.0374 (7)	0.0303 (8)	0.0114 (6)	−0.0036 (6)	0.0067 (6)
N3	0.0463 (8)	0.0594 (9)	0.0304 (8)	0.0256 (7)	0.0011 (6)	0.0093 (7)
C3	0.0366 (9)	0.0580 (11)	0.0355 (10)	0.0103 (8)	0.0035 (7)	0.0095 (9)
C2	0.0309 (8)	0.0451 (9)	0.0288 (9)	0.0094 (7)	0.0026 (6)	0.0066 (7)
C1	0.0360 (9)	0.0391 (9)	0.0352 (10)	0.0110 (7)	0.0036 (7)	0.0101 (7)
C10	0.0294 (8)	0.0334 (8)	0.0299 (9)	0.0095 (6)	0.0043 (6)	0.0050 (7)
C9	0.0343 (8)	0.0364 (8)	0.0294 (9)	0.0110 (7)	0.0029 (6)	0.0019 (7)
C8	0.0313 (8)	0.0392 (9)	0.0317 (9)	0.0120 (7)	0.0019 (6)	0.0063 (7)
C11	0.0556 (11)	0.0424 (9)	0.0324 (10)	0.0145 (8)	0.0008 (8)	0.0043 (7)
C12	0.0492 (10)	0.0546 (10)	0.0301 (10)	0.0120 (8)	0.0003 (8)	0.0037 (8)
C4	0.0298 (8)	0.0431 (9)	0.0305 (9)	0.0095 (7)	0.0044 (7)	−0.0005 (8)
C5	0.0291 (8)	0.0390 (8)	0.0303 (9)	0.0118 (7)	0.0040 (6)	0.0036 (7)
C6	0.0383 (9)	0.0363 (8)	0.0339 (10)	0.0120 (7)	0.0022 (7)	−0.0030 (7)
C7	0.0402 (9)	0.0324 (8)	0.0415 (10)	0.0150 (7)	0.0023 (7)	0.0052 (7)
C14	0.0539 (11)	0.0479 (10)	0.0385 (10)	0.0084 (8)	−0.0037 (8)	0.0134 (8)
C13	0.0707 (12)	0.0468 (10)	0.0380 (11)	0.0214 (9)	−0.0029 (9)	0.0094 (8)
C15	0.0612 (11)	0.0350 (9)	0.0381 (10)	0.0214 (8)	0.0009 (8)	0.0007 (7)
C16	0.0714 (13)	0.0448 (10)	0.0596 (13)	0.0095 (9)	−0.0065 (10)	−0.0081 (9)
C5'	0.1024 (18)	0.0834 (16)	0.0710 (17)	0.0610 (14)	−0.0079 (13)	0.0074 (13)
C6'	0.0801 (14)	0.0640 (12)	0.0493 (12)	0.0373 (11)	−0.0020 (10)	0.0087 (10)
C1'	0.0527 (11)	0.0370 (9)	0.0393 (11)	0.0139 (8)	−0.0038 (8)	0.0034 (7)
C2'	0.0656 (12)	0.0385 (9)	0.0406 (11)	0.0104 (9)	−0.0026 (9)	0.0033 (8)
C7'	0.0512 (11)	0.0490 (10)	0.0423 (12)	0.0184 (9)	0.0012 (9)	0.0089 (8)
C4'	0.1052 (19)	0.0601 (13)	0.0657 (17)	0.0367 (13)	−0.0294 (14)	0.0091 (11)
C3'	0.0963 (17)	0.0536 (12)	0.0419 (12)	0.0172 (12)	−0.0087 (11)	0.0109 (10)

Geometric parameters (Å, º)

F1—C7	1.3640 (17)	C11—H11	0.9700
O2—C3	1.328 (2)	C11—H10	0.9700
O2—H2	0.95 (2)	C12—H13	0.9700
O1S—H1A	0.80 (3)	C12—H12	0.9700
O1S—H1B	0.89 (3)	C4—C5	1.447 (2)
O1—C3	1.208 (2)	C5—C6	1.404 (2)
O3—C4	1.2601 (17)	C6—C7	1.345 (2)
O3'—C2'	1.352 (2)	C6—H9	0.9300
O3'—H1'	0.97 (3)	C14—C13	1.510 (2)
O2'—C7'	1.258 (2)	C14—H18	0.9700
O1'—C7'	1.253 (2)	C14—H19	0.9700
N1—C1	1.3418 (18)	C13—H16	0.9700
N1—C10	1.3974 (18)	C13—H17	0.9700
N1—C15	1.4812 (19)	C15—C16	1.500 (3)
N2—C8	1.3903 (18)	C15—H4	0.9700
N2—C11	1.463 (2)	C15—H3	0.9700
N2—C14	1.476 (2)	C16—H7	0.9600
N3—C13	1.476 (2)	C16—H6	0.9600
N3—C12	1.484 (2)	C16—H5	0.9600
N3—H15	0.9000	C5'—C4'	1.379 (3)
N3—H14	0.9000	C5'—C6'	1.382 (3)
C3—C2	1.483 (2)	C5'—H4'	0.9300
C2—C1	1.361 (2)	C6'—C1'	1.386 (3)
C2—C4	1.426 (2)	C6'—H5'	0.9300
C1—H1	0.9300	C1'—C2'	1.398 (2)
C10—C5	1.402 (2)	C1'—C7'	1.493 (2)
C10—C9	1.405 (2)	C2'—C3'	1.387 (3)
C9—C8	1.395 (2)	C4'—C3'	1.354 (3)
C9—H8	0.9300	C4'—H3'	0.9300
C8—C7	1.414 (2)	C3'—H2'	0.9300
C11—C12	1.515 (2)
C3—O2—H2	108.0 (13)	C7—C6—C5	120.87 (14)
H1A—O1S—H1B	114 (3)	C7—C6—H9	119.6
C2'—O3'—H1'	104.9 (16)	C5—C6—H9	119.6
C1—N1—C10	119.23 (13)	C6—C7—F1	117.43 (14)
C1—N1—C15	118.55 (12)	C6—C7—C8	123.65 (14)
C10—N1—C15	122.21 (12)	F1—C7—C8	118.87 (14)
C8—N2—C11	118.27 (12)	N2—C14—C13	109.84 (14)
C8—N2—C14	118.60 (12)	N2—C14—H18	109.7
C11—N2—C14	110.54 (13)	C13—C14—H18	109.7
C13—N3—C12	111.16 (13)	N2—C14—H19	109.7
C13—N3—H15	109.4	C13—C14—H19	109.7
C12—N3—H15	109.4	H18—C14—H19	108.2
C13—N3—H14	109.4	N3—C13—C14	109.97 (14)
C12—N3—H14	109.4	N3—C13—H16	109.7
H15—N3—H14	108.0	C14—C13—H16	109.7
O1—C3—O2	120.98 (16)	N3—C13—H17	109.7
O1—C3—C2	123.45 (16)	C14—C13—H17	109.7
O2—C3—C2	115.55 (15)	H16—C13—H17	108.2
C1—C2—C4	119.56 (14)	N1—C15—C16	111.80 (14)
C1—C2—C3	117.94 (15)	N1—C15—H4	109.3
C4—C2—C3	122.41 (14)	C16—C15—H4	109.3
N1—C1—C2	124.95 (14)	N1—C15—H3	109.3
N1—C1—H1	117.5	C16—C15—H3	109.3
C2—C1—H1	117.5	H4—C15—H3	107.9
N1—C10—C5	118.62 (13)	C15—C16—H7	109.5
N1—C10—C9	121.15 (13)	C15—C16—H6	109.5
C5—C10—C9	120.20 (13)	H7—C16—H6	109.5
C8—C9—C10	121.96 (14)	C15—C16—H5	109.5
C8—C9—H8	119.0	H7—C16—H5	109.5
C10—C9—H8	119.0	H6—C16—H5	109.5
N2—C8—C9	122.61 (14)	C4'—C5'—C6'	118.6 (2)
N2—C8—C7	121.77 (13)	C4'—C5'—H4'	120.7
C9—C8—C7	115.49 (14)	C6'—C5'—H4'	120.7
N2—C11—C12	110.59 (13)	C5'—C6'—C1'	121.4 (2)
N2—C11—H11	109.5	C5'—C6'—H5'	119.3
C12—C11—H11	109.5	C1'—C6'—H5'	119.3
N2—C11—H10	109.5	C6'—C1'—C2'	118.57 (17)
C12—C11—H10	109.5	C6'—C1'—C7'	120.57 (17)
H11—C11—H10	108.1	C2'—C1'—C7'	120.84 (18)
N3—C12—C11	112.33 (13)	O3'—C2'—C3'	118.51 (19)
N3—C12—H13	109.1	O3'—C2'—C1'	121.81 (16)
C11—C12—H13	109.1	C3'—C2'—C1'	119.7 (2)
N3—C12—H12	109.1	O1'—C7'—O2'	122.89 (16)
C11—C12—H12	109.1	O1'—C7'—C1'	119.16 (17)
H13—C12—H12	107.9	O2'—C7'—C1'	117.94 (17)
O3—C4—C2	122.77 (14)	C3'—C4'—C5'	121.5 (2)
O3—C4—C5	121.69 (14)	C3'—C4'—H3'	119.3
C2—C4—C5	115.54 (13)	C5'—C4'—H3'	119.3
C10—C5—C6	117.79 (14)	C4'—C3'—C2'	120.3 (2)
C10—C5—C4	121.94 (13)	C4'—C3'—H2'	119.8
C6—C5—C4	120.26 (14)	C2'—C3'—H2'	119.8
O1—C3—C2—C1	8.3 (2)	C2—C4—C5—C10	2.1 (2)
O2—C3—C2—C1	−170.36 (14)	O3—C4—C5—C6	2.1 (2)
O1—C3—C2—C4	−174.96 (16)	C2—C4—C5—C6	−178.06 (14)
O2—C3—C2—C4	6.4 (2)	C10—C5—C6—C7	−1.7 (2)
C10—N1—C1—C2	2.0 (2)	C4—C5—C6—C7	178.48 (14)
C15—N1—C1—C2	−178.85 (15)	C5—C6—C7—F1	−175.05 (14)
C4—C2—C1—N1	1.6 (2)	C5—C6—C7—C8	2.2 (2)
C3—C2—C1—N1	178.50 (14)	N2—C8—C7—C6	−176.70 (15)
C1—N1—C10—C5	−3.4 (2)	C9—C8—C7—C6	−0.8 (2)
C15—N1—C10—C5	177.49 (14)	N2—C8—C7—F1	0.5 (2)
C1—N1—C10—C9	178.11 (13)	C9—C8—C7—F1	176.40 (14)
C15—N1—C10—C9	−1.0 (2)	C8—N2—C14—C13	157.90 (14)
N1—C10—C9—C8	179.83 (14)	C11—N2—C14—C13	−60.81 (19)
C5—C10—C9—C8	1.4 (2)	C12—N3—C13—C14	−55.73 (19)
C11—N2—C8—C9	−4.9 (2)	N2—C14—C13—N3	59.7 (2)
C14—N2—C8—C9	133.47 (16)	C1—N1—C15—C16	−93.40 (17)
C11—N2—C8—C7	170.78 (15)	C10—N1—C15—C16	85.68 (18)
C14—N2—C8—C7	−50.9 (2)	C4'—C5'—C6'—C1'	0.6 (3)
C10—C9—C8—N2	174.89 (13)	C5'—C6'—C1'—C2'	−0.4 (3)
C10—C9—C8—C7	−1.0 (2)	C5'—C6'—C1'—C7'	−179.03 (18)
C8—N2—C11—C12	−161.49 (14)	C6'—C1'—C2'—O3'	179.05 (17)
C14—N2—C11—C12	57.07 (18)	C7'—C1'—C2'—O3'	−2.3 (3)
C13—N3—C12—C11	52.96 (19)	C6'—C1'—C2'—C3'	−1.0 (3)
N2—C11—C12—N3	−53.34 (19)	C7'—C1'—C2'—C3'	177.68 (16)
C1—C2—C4—O3	176.24 (14)	C6'—C1'—C7'—O1'	1.4 (3)
C3—C2—C4—O3	−0.5 (2)	C2'—C1'—C7'—O1'	−177.18 (15)
C1—C2—C4—C5	−3.6 (2)	C6'—C1'—C7'—O2'	−179.73 (17)
C3—C2—C4—C5	179.71 (13)	C2'—C1'—C7'—O2'	1.7 (2)
N1—C10—C5—C6	−178.50 (13)	C6'—C5'—C4'—C3'	0.5 (3)
C9—C10—C5—C6	0.0 (2)	C5'—C4'—C3'—C2'	−1.9 (3)
N1—C10—C5—C4	1.3 (2)	O3'—C2'—C3'—C4'	−177.92 (19)
C9—C10—C5—C4	179.79 (13)	C1'—C2'—C3'—C4'	2.1 (3)
O3—C4—C5—C10	−177.68 (14)

(mo_2014070_0m)

Crystal data

C23H26FN3O7	V = 3394.48 (14) Å^3
Mr = 475.47	Z = 6
Triclinic, P1	F(000) = 1500.0
a = 7.3258 (2) Å	Dx = 1.396 Mg m^−3
b = 19.8297 (4) Å	Mo Kα radiation, λ = 0.71073 Å
c = 23.9108 (5) Å	µ = 0.11 mm^−1
α = 96.924 (1)°	T = 296 K
β = 97.210 (1)°	Block, colorless
γ = 96.143 (1)°	0.60 × 0.15 × 0.08 mm

Data collection

CCD area detector diffractometer	15579 independent reflections
Radiation source: fine-focus sealed tube	7689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
phi and ω scans	θmax = 27.6°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements) SADABS	h = −9→9
Tmin = 0.938, Tmax = 0.991	k = −25→25
49327 measured reflections	l = −31→31

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.122	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ^2(Fo^2) + (0.0525P)^2] where P = (Fo^2 + 2Fc^2)/3
15579 reflections	(Δ/σ)max = 0.001
972 parameters	Δρmax = 0.18 e Å^−3
3 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1A	0.7955 (2)	1.07985 (6)	0.11286 (5)	0.0629 (4)
F1B	0.7742 (2)	0.23097 (6)	0.17775 (5)	0.0674 (4)
F1C	0.61707 (19)	0.44309 (5)	0.52686 (5)	0.0591 (4)
O1S	0.4439 (3)	0.93045 (9)	0.35161 (7)	0.0573 (5)
O2A	0.6976 (2)	1.00321 (8)	−0.20252 (6)	0.0585 (4)
H2	0.697 (4)	1.0320 (11)	−0.1691 (8)	0.088*
O2S	0.2387 (3)	0.41258 (9)	0.97820 (7)	0.0597 (5)
O1A	0.7431 (3)	0.89563 (9)	−0.22413 (7)	0.0895 (7)
O3S	0.9420 (3)	0.75184 (9)	0.30124 (8)	0.0638 (5)
O3A	0.7047 (2)	1.05282 (7)	−0.09915 (6)	0.0545 (4)
N3B	0.8813 (3)	0.44907 (10)	0.07972 (7)	0.0402 (4)
O3B	0.9994 (2)	0.25550 (7)	0.38534 (6)	0.0614 (5)
O1B	1.0983 (3)	0.41470 (9)	0.51593 (7)	0.0781 (6)
O1X	0.38485 (19)	0.59125 (7)	0.01692 (5)	0.0461 (4)
O3X	0.6899 (2)	0.64382 (8)	0.28104 (6)	0.0542 (4)
H37	0.770 (4)	0.6763 (12)	0.2844 (11)	0.081*
O2X	0.1774 (2)	0.52359 (7)	0.05002 (6)	0.0509 (4)
O2C	0.2724 (2)	0.39749 (8)	0.21771 (6)	0.0583 (4)
H42	0.302 (4)	0.4248 (12)	0.2540 (11)	0.087*
O1C	0.2573 (2)	0.28815 (8)	0.18309 (6)	0.0663 (5)
O3C	0.3857 (2)	0.43833 (7)	0.32027 (6)	0.0548 (4)
O2Y	1.1302 (2)	0.14711 (8)	0.61848 (6)	0.0560 (4)
O3Y	0.6980 (2)	0.03789 (7)	0.37222 (6)	0.0472 (4)
H61	0.607 (3)	0.0013 (11)	0.3662 (9)	0.071*
O1Y	0.9277 (2)	0.06708 (7)	0.63958 (5)	0.0523 (4)
O2Z	0.5014 (2)	0.84186 (8)	0.25919 (6)	0.0592 (4)
O3Z	0.0121 (2)	0.69531 (7)	0.03106 (6)	0.0555 (4)
H66	−0.067 (4)	0.6616 (12)	0.0297 (10)	0.083*
O1Z	0.3153 (2)	0.76659 (7)	0.29379 (6)	0.0511 (4)
N3A	0.8493 (2)	0.91589 (9)	0.25997 (7)	0.0478 (5)
H14A	0.9085	0.9194	0.2957	0.057*
H15A	0.7401	0.8895	0.2579	0.057*
N2A	0.8444 (2)	0.95121 (8)	0.14637 (6)	0.0392 (4)
N1A	0.7837 (2)	0.86367 (8)	−0.05532 (6)	0.0420 (4)
O2B	1.0967 (3)	0.30424 (9)	0.48763 (7)	0.0695 (5)
H20	1.079 (4)	0.2755 (12)	0.4556 (9)	0.104*
N2B	0.7197 (2)	0.35753 (8)	0.14918 (6)	0.0407 (4)
N1B	0.8951 (2)	0.44633 (8)	0.35144 (7)	0.0388 (4)
N1C	0.4645 (2)	0.24137 (7)	0.34275 (6)	0.0348 (4)
N2C	0.6529 (2)	0.31159 (8)	0.54633 (6)	0.0396 (4)
N3C	0.4594 (2)	0.21423 (8)	0.60513 (6)	0.0408 (4)
H14C	0.3626	0.1825	0.6061	0.049*
H15C	0.5333	0.2189	0.6388	0.049*
C12A	0.8158 (4)	0.98485 (11)	0.24622 (8)	0.0579 (7)
H15	0.9326	1.0145	0.2515	0.069*
H16	0.7366	1.0046	0.2717	0.069*
C11A	0.7250 (3)	0.97978 (11)	0.18559 (8)	0.0511 (6)
H17	0.6072	0.9508	0.1805	0.061*
H9	0.7010	1.0249	0.1771	0.061*
C8A	0.8067 (3)	0.95979 (10)	0.08890 (8)	0.0353 (5)
C9A	0.8022 (3)	0.90672 (10)	0.04483 (8)	0.0382 (5)
H19	0.8151	0.8629	0.0536	0.046*
C10A	0.7788 (3)	0.91744 (9)	−0.01227 (8)	0.0352 (5)
C5A	0.7522 (3)	0.98208 (10)	−0.02700 (8)	0.0361 (5)
C4A	0.7292 (3)	0.99433 (10)	−0.08589 (8)	0.0397 (5)
C2A	0.7393 (3)	0.93709 (10)	−0.12678 (8)	0.0419 (5)
C3A	0.7267 (3)	0.94249 (13)	−0.18859 (9)	0.0541 (6)
C15A	0.8012 (4)	0.79303 (10)	−0.04313 (9)	0.0576 (7)
H6	0.8896	0.7945	−0.0091	0.069*
H7	0.8484	0.7679	−0.0744	0.069*
C16A	0.6184 (4)	0.75643 (12)	−0.03486 (12)	0.0956 (10)
H4	0.5713	0.7813	−0.0039	0.143*
H3	0.6350	0.7112	−0.0263	0.143*
H5	0.5321	0.7533	−0.0690	0.143*
C1A	0.7636 (3)	0.87525 (10)	−0.10978 (8)	0.0466 (6)
H8	0.7665	0.8386	−0.1377	0.056*
C13A	0.9623 (3)	0.88374 (11)	0.21982 (8)	0.0483 (6)
H14	0.9729	0.8372	0.2272	0.058*
H13	1.0861	0.9086	0.2263	0.058*
C14A	0.8807 (3)	0.88270 (10)	0.15856 (8)	0.0453 (5)
H12	0.9659	0.8655	0.1340	0.054*
H11	0.7658	0.8519	0.1504	0.054*
C7A	0.7826 (3)	1.02465 (10)	0.07221 (8)	0.0416 (5)
C6A	0.7539 (3)	1.03562 (10)	0.01707 (8)	0.0418 (5)
H18	0.7351	1.0791	0.0084	0.050*
C3B	1.0677 (3)	0.36715 (14)	0.47835 (10)	0.0535 (6)
C2B	0.9971 (3)	0.37282 (11)	0.41794 (8)	0.0414 (5)
C4B	0.9691 (3)	0.31477 (10)	0.37511 (9)	0.0410 (5)
C5B	0.9022 (3)	0.32714 (9)	0.31833 (8)	0.0364 (5)
C6B	0.8707 (3)	0.27313 (10)	0.27308 (9)	0.0438 (5)
H29	0.8910	0.2292	0.2799	0.053*
C7B	0.8111 (3)	0.28471 (10)	0.21980 (9)	0.0430 (5)
C8B	0.7801 (3)	0.35017 (10)	0.20572 (8)	0.0367 (5)
C11B	0.8294 (3)	0.33375 (10)	0.10531 (8)	0.0463 (6)
H35	0.7475	0.3176	0.0700	0.056*
H34	0.8906	0.2956	0.1168	0.056*
C12B	0.9719 (3)	0.38935 (10)	0.09551 (8)	0.0427 (5)
H36	1.0602	0.4031	0.1298	0.051*
H21	1.0389	0.3725	0.0653	0.051*
C10B	0.8659 (3)	0.39229 (9)	0.30657 (8)	0.0330 (5)
C1B	0.9602 (3)	0.43522 (11)	0.40400 (8)	0.0437 (5)
H22	0.9815	0.4723	0.4328	0.052*
C15B	0.8701 (3)	0.51756 (9)	0.34208 (9)	0.0497 (6)
H26	0.8508	0.5435	0.3775	0.060*
H27	0.7610	0.5172	0.3144	0.060*
C16B	1.0380 (4)	0.55186 (12)	0.32087 (13)	0.0881 (9)
H25	1.1461	0.5522	0.3482	0.132*
H24	1.0196	0.5981	0.3158	0.132*
H23	1.0547	0.5271	0.2852	0.132*
C9B	0.8051 (3)	0.40279 (9)	0.25048 (8)	0.0359 (5)
H28	0.7811	0.4463	0.2433	0.043*
C14B	0.6382 (3)	0.41886 (10)	0.13656 (8)	0.0440 (5)
H32	0.5770	0.4354	0.1683	0.053*
H33	0.5446	0.4069	0.1033	0.053*
C13B	0.7786 (3)	0.47590 (10)	0.12564 (8)	0.0423 (5)
H31	0.7157	0.5138	0.1143	0.051*
H30	0.8643	0.4924	0.1601	0.051*
C7X	0.3180 (3)	0.56731 (10)	0.05772 (8)	0.0352 (5)
C1X	0.4142 (3)	0.58990 (9)	0.11700 (7)	0.0313 (4)
C2X	0.3723 (3)	0.55389 (9)	0.16120 (8)	0.0386 (5)
H41	0.2803	0.5166	0.1539	0.046*
C3X	0.4649 (3)	0.57256 (10)	0.21558 (8)	0.0415 (5)
H40	0.4365	0.5476	0.2446	0.050*
C4X	0.6000 (3)	0.62839 (10)	0.22693 (8)	0.0377 (5)
C5X	0.6410 (3)	0.66594 (9)	0.18382 (8)	0.0366 (5)
H38	0.7303	0.7041	0.1916	0.044*
C6X	0.5491 (3)	0.64641 (9)	0.12956 (8)	0.0353 (5)
H39	0.5778	0.6715	0.1007	0.042*
C3C	0.2952 (3)	0.33294 (12)	0.22322 (9)	0.0459 (5)
C2C	0.3684 (3)	0.32204 (10)	0.28185 (8)	0.0363 (5)
C1C	0.3980 (3)	0.25718 (10)	0.29165 (8)	0.0384 (5)
H60	0.3705	0.2221	0.2612	0.046*
C10C	0.5016 (3)	0.29211 (9)	0.38985 (8)	0.0317 (4)
C9C	0.5623 (3)	0.27622 (9)	0.44424 (8)	0.0348 (5)
H53	0.5823	0.2314	0.4483	0.042*
C8C	0.5931 (3)	0.32498 (9)	0.49173 (8)	0.0339 (5)
C11C	0.5491 (3)	0.33348 (10)	0.59265 (8)	0.0485 (6)
H45	0.5009	0.3759	0.5860	0.058*
H46	0.6321	0.3420	0.6284	0.058*
C12C	0.3911 (3)	0.28006 (10)	0.59678 (8)	0.0459 (6)
H47	0.3278	0.2952	0.6284	0.055*
H48	0.3029	0.2741	0.5622	0.055*
C5C	0.4741 (3)	0.35960 (9)	0.38255 (8)	0.0339 (5)
C4C	0.4074 (3)	0.37672 (10)	0.32706 (8)	0.0379 (5)
C6C	0.5134 (3)	0.41005 (9)	0.43020 (8)	0.0390 (5)
H54	0.4995	0.4554	0.4262	0.047*
C7C	0.5714 (3)	0.39293 (9)	0.48187 (8)	0.0397 (5)
C14C	0.7174 (3)	0.24567 (10)	0.55397 (8)	0.0435 (5)
H52	0.8077	0.2516	0.5881	0.052*
H51	0.7794	0.2309	0.5219	0.052*
C13C	0.5643 (3)	0.19066 (10)	0.55886 (8)	0.0437 (5)
H49	0.4815	0.1801	0.5231	0.052*
H50	0.6165	0.1493	0.5669	0.052*
C15C	0.4871 (3)	0.16892 (9)	0.34791 (8)	0.0423 (5)
H58	0.5996	0.1671	0.3735	0.051*
H59	0.5001	0.1453	0.3109	0.051*
C16C	0.3241 (4)	0.13275 (10)	0.37001 (10)	0.0622 (7)
H57	0.3136	0.1549	0.4072	0.093*
H55	0.3426	0.0859	0.3721	0.093*
H56	0.2125	0.1345	0.3447	0.093*
C7Y	0.9997 (3)	0.09965 (10)	0.60404 (8)	0.0384 (5)
C1Y	0.9214 (3)	0.08205 (9)	0.54257 (8)	0.0322 (5)
C6Y	0.7878 (3)	0.02642 (9)	0.52425 (8)	0.0353 (5)
H62	0.7489	−0.0010	0.5505	0.042*
C5Y	0.7110 (3)	0.01073 (9)	0.46794 (8)	0.0366 (5)
H63	0.6204	−0.0267	0.4566	0.044*
C4Y	0.7690 (3)	0.05086 (9)	0.42805 (8)	0.0342 (5)
C2Y	0.9784 (3)	0.12140 (9)	0.50220 (8)	0.0380 (5)
H65	1.0697	0.1586	0.5135	0.046*
C3Y	0.9027 (3)	0.10658 (9)	0.44579 (8)	0.0394 (5)
H64	0.9416	0.1341	0.4196	0.047*
C7Z	0.3736 (3)	0.79272 (10)	0.25281 (8)	0.0393 (5)
C1Z	0.2806 (3)	0.76558 (9)	0.19395 (8)	0.0330 (5)
C2Z	0.3154 (3)	0.79869 (9)	0.14779 (8)	0.0404 (5)
H69	0.4015	0.8378	0.1535	0.048*
C3Z	0.2257 (3)	0.77513 (10)	0.09373 (8)	0.0426 (5)
H70	0.2499	0.7984	0.0634	0.051*
C4Z	0.0996 (3)	0.71671 (9)	0.08486 (8)	0.0362 (5)
C6Z	0.1533 (3)	0.70685 (9)	0.18404 (8)	0.0360 (5)
H67	0.1285	0.6835	0.2143	0.043*
C5Z	0.0633 (3)	0.68257 (9)	0.13014 (8)	0.0368 (5)
H68	−0.0218	0.6432	0.1242	0.044*
H14B	0.796 (3)	0.4345 (10)	0.0462 (9)	0.052 (6)*
H15B	0.971 (3)	0.4808 (10)	0.0721 (8)	0.047 (6)*
H2B	0.218 (4)	0.4477 (13)	0.9989 (11)	0.080 (9)*
H2A	0.360 (5)	0.4091 (14)	0.9835 (12)	0.108 (12)*
H3A	0.920 (4)	0.7864 (10)	0.3238 (9)	0.078 (9)*
H3B	1.061 (4)	0.7537 (13)	0.2991 (11)	0.089 (10)*
H1A	0.455 (4)	0.9007 (13)	0.3230 (11)	0.089 (10)*
H1B	0.320 (5)	0.9350 (15)	0.3499 (12)	0.119 (13)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.0962 (11)	0.0471 (7)	0.0435 (7)	0.0130 (7)	0.0104 (7)	−0.0055 (6)
F1B	0.1064 (12)	0.0407 (7)	0.0514 (8)	0.0019 (7)	0.0083 (8)	0.0009 (6)
F1C	0.0921 (11)	0.0382 (6)	0.0436 (7)	0.0070 (7)	0.0042 (7)	−0.0021 (6)
O1S	0.0518 (12)	0.0613 (11)	0.0502 (11)	−0.0064 (10)	0.0035 (9)	−0.0116 (8)
O2A	0.0585 (11)	0.0766 (12)	0.0440 (9)	0.0067 (9)	0.0033 (8)	0.0278 (8)
O2S	0.0439 (12)	0.0601 (11)	0.0668 (12)	−0.0042 (10)	0.0107 (9)	−0.0178 (9)
O1A	0.157 (2)	0.0713 (12)	0.0333 (9)	−0.0029 (12)	0.0057 (11)	0.0026 (9)
O3S	0.0543 (13)	0.0644 (12)	0.0636 (12)	−0.0106 (10)	0.0136 (10)	−0.0169 (9)
O3A	0.0684 (12)	0.0502 (9)	0.0478 (9)	0.0113 (8)	0.0029 (8)	0.0201 (7)
N3B	0.0370 (11)	0.0538 (11)	0.0277 (10)	−0.0042 (10)	0.0003 (9)	0.0102 (9)
O3B	0.0784 (13)	0.0513 (9)	0.0611 (10)	0.0195 (9)	0.0060 (9)	0.0280 (8)
O1B	0.0996 (16)	0.0926 (13)	0.0394 (10)	0.0176 (12)	−0.0063 (10)	0.0099 (10)
O1X	0.0399 (9)	0.0633 (9)	0.0319 (8)	−0.0042 (8)	0.0002 (7)	0.0083 (7)
O3X	0.0616 (12)	0.0602 (10)	0.0330 (8)	−0.0071 (8)	−0.0068 (8)	0.0016 (7)
O2X	0.0383 (9)	0.0642 (9)	0.0418 (9)	−0.0131 (8)	0.0026 (7)	−0.0064 (7)
O2C	0.0677 (12)	0.0632 (11)	0.0458 (9)	0.0117 (9)	−0.0035 (9)	0.0238 (8)
O1C	0.0868 (14)	0.0721 (11)	0.0373 (9)	0.0110 (10)	−0.0034 (9)	0.0080 (8)
O3C	0.0730 (12)	0.0447 (9)	0.0501 (9)	0.0166 (8)	0.0020 (8)	0.0185 (7)
O2Y	0.0407 (10)	0.0722 (10)	0.0446 (9)	−0.0166 (9)	0.0030 (7)	−0.0106 (8)
O3Y	0.0554 (10)	0.0541 (9)	0.0288 (8)	−0.0006 (8)	0.0005 (7)	0.0040 (7)
O1Y	0.0475 (10)	0.0735 (10)	0.0317 (8)	−0.0075 (8)	0.0003 (7)	0.0094 (7)
O2Z	0.0451 (10)	0.0720 (10)	0.0494 (9)	−0.0182 (9)	0.0034 (7)	−0.0105 (8)
O3Z	0.0661 (12)	0.0570 (10)	0.0348 (8)	−0.0077 (8)	−0.0099 (8)	0.0039 (8)
O1Z	0.0474 (10)	0.0686 (10)	0.0321 (8)	−0.0038 (8)	−0.0035 (7)	0.0057 (7)
N3A	0.0418 (11)	0.0717 (12)	0.0284 (9)	−0.0044 (10)	0.0033 (8)	0.0121 (9)
N2A	0.0401 (11)	0.0525 (10)	0.0274 (9)	0.0137 (9)	0.0056 (8)	0.0067 (8)
N1A	0.0563 (12)	0.0380 (9)	0.0295 (9)	0.0027 (9)	0.0007 (8)	0.0045 (8)
O2B	0.0798 (13)	0.0786 (13)	0.0549 (11)	0.0207 (11)	−0.0036 (10)	0.0322 (9)
N2B	0.0457 (11)	0.0475 (10)	0.0302 (9)	0.0053 (9)	0.0076 (8)	0.0088 (8)
N1B	0.0444 (11)	0.0401 (9)	0.0332 (10)	0.0084 (8)	0.0043 (8)	0.0094 (8)
N1C	0.0415 (11)	0.0355 (9)	0.0289 (9)	0.0070 (8)	0.0069 (8)	0.0069 (7)
N2C	0.0457 (11)	0.0440 (10)	0.0299 (9)	0.0048 (9)	0.0047 (8)	0.0091 (8)
N3C	0.0367 (11)	0.0542 (11)	0.0286 (9)	−0.0046 (9)	−0.0019 (8)	0.0092 (8)
C12A	0.0705 (18)	0.0692 (16)	0.0358 (13)	0.0102 (14)	0.0159 (12)	0.0045 (11)
C11A	0.0498 (15)	0.0697 (15)	0.0388 (13)	0.0193 (13)	0.0135 (11)	0.0093 (11)
C8A	0.0316 (12)	0.0450 (12)	0.0296 (11)	0.0044 (10)	0.0022 (9)	0.0083 (9)
C9A	0.0441 (14)	0.0398 (11)	0.0309 (11)	0.0042 (10)	0.0034 (10)	0.0080 (9)
C10A	0.0351 (12)	0.0376 (11)	0.0321 (11)	0.0015 (10)	0.0041 (9)	0.0054 (9)
C5A	0.0336 (12)	0.0414 (11)	0.0325 (11)	0.0022 (10)	0.0008 (9)	0.0083 (9)
C4A	0.0383 (13)	0.0440 (12)	0.0371 (12)	−0.0004 (10)	0.0027 (10)	0.0138 (10)
C2A	0.0449 (14)	0.0465 (12)	0.0318 (11)	−0.0035 (11)	0.0005 (10)	0.0089 (10)
C3A	0.0599 (17)	0.0619 (16)	0.0376 (14)	−0.0058 (13)	0.0003 (12)	0.0137 (12)
C15A	0.093 (2)	0.0394 (12)	0.0417 (13)	0.0164 (14)	0.0039 (13)	0.0069 (10)
C16A	0.107 (3)	0.0622 (17)	0.105 (2)	−0.0318 (17)	−0.0184 (19)	0.0330 (16)
C1A	0.0564 (16)	0.0477 (13)	0.0321 (12)	−0.0015 (11)	0.0027 (11)	0.0013 (10)
C13A	0.0436 (14)	0.0666 (14)	0.0383 (12)	0.0092 (12)	0.0076 (11)	0.0176 (11)
C14A	0.0500 (15)	0.0560 (13)	0.0331 (12)	0.0145 (12)	0.0062 (10)	0.0110 (10)
C7A	0.0454 (14)	0.0424 (12)	0.0361 (12)	0.0072 (11)	0.0067 (10)	−0.0008 (10)
C6A	0.0445 (14)	0.0405 (11)	0.0420 (13)	0.0077 (10)	0.0052 (10)	0.0111 (10)
C3B	0.0473 (15)	0.0736 (17)	0.0445 (15)	0.0116 (14)	0.0077 (12)	0.0231 (13)
C2B	0.0351 (13)	0.0557 (13)	0.0369 (12)	0.0095 (11)	0.0052 (10)	0.0165 (11)
C4B	0.0334 (13)	0.0489 (13)	0.0458 (13)	0.0073 (11)	0.0081 (10)	0.0217 (11)
C5B	0.0341 (12)	0.0387 (11)	0.0396 (12)	0.0052 (10)	0.0086 (10)	0.0133 (10)
C6B	0.0503 (15)	0.0356 (11)	0.0490 (14)	0.0068 (11)	0.0104 (11)	0.0154 (10)
C7B	0.0521 (15)	0.0349 (11)	0.0420 (13)	0.0015 (11)	0.0110 (11)	0.0040 (10)
C8B	0.0350 (13)	0.0418 (12)	0.0355 (12)	0.0020 (10)	0.0111 (10)	0.0100 (9)
C11B	0.0587 (16)	0.0482 (12)	0.0313 (11)	0.0043 (12)	0.0095 (11)	0.0011 (10)
C12B	0.0428 (14)	0.0583 (13)	0.0279 (11)	0.0086 (12)	0.0079 (10)	0.0041 (10)
C10B	0.0286 (12)	0.0374 (11)	0.0349 (11)	0.0033 (9)	0.0089 (9)	0.0092 (9)
C1B	0.0444 (14)	0.0508 (13)	0.0358 (12)	0.0063 (11)	0.0045 (10)	0.0064 (10)
C15B	0.0653 (17)	0.0370 (12)	0.0450 (13)	0.0137 (12)	−0.0030 (12)	0.0034 (10)
C16B	0.074 (2)	0.0508 (15)	0.135 (3)	−0.0094 (15)	−0.0122 (18)	0.0342 (16)
C9B	0.0376 (13)	0.0384 (11)	0.0354 (12)	0.0055 (10)	0.0096 (10)	0.0141 (9)
C14B	0.0380 (13)	0.0612 (14)	0.0359 (12)	0.0104 (12)	0.0055 (10)	0.0148 (10)
C13B	0.0481 (14)	0.0470 (12)	0.0348 (12)	0.0083 (11)	0.0092 (10)	0.0116 (10)
C7X	0.0298 (12)	0.0401 (11)	0.0341 (12)	0.0048 (10)	0.0018 (9)	0.0012 (9)
C1X	0.0276 (11)	0.0337 (10)	0.0315 (11)	0.0041 (9)	0.0042 (9)	0.0001 (8)
C2X	0.0363 (13)	0.0370 (11)	0.0396 (12)	−0.0011 (10)	0.0026 (10)	0.0014 (9)
C3X	0.0479 (14)	0.0421 (12)	0.0333 (12)	−0.0009 (11)	0.0029 (10)	0.0094 (9)
C4X	0.0407 (13)	0.0419 (11)	0.0271 (11)	0.0056 (11)	−0.0020 (9)	−0.0026 (9)
C5X	0.0360 (13)	0.0345 (10)	0.0359 (12)	−0.0020 (10)	0.0042 (10)	−0.0014 (9)
C6X	0.0367 (12)	0.0365 (11)	0.0328 (11)	0.0045 (10)	0.0051 (9)	0.0048 (9)
C3C	0.0425 (14)	0.0565 (14)	0.0427 (14)	0.0062 (12)	0.0092 (11)	0.0198 (12)
C2C	0.0327 (12)	0.0450 (12)	0.0340 (11)	0.0063 (10)	0.0053 (9)	0.0138 (10)
C1C	0.0383 (13)	0.0466 (12)	0.0311 (11)	0.0049 (10)	0.0074 (9)	0.0061 (9)
C10C	0.0322 (12)	0.0341 (10)	0.0306 (11)	0.0045 (9)	0.0098 (9)	0.0058 (9)
C9C	0.0408 (13)	0.0326 (10)	0.0347 (11)	0.0090 (10)	0.0105 (9)	0.0101 (9)
C8C	0.0353 (12)	0.0377 (11)	0.0303 (11)	0.0038 (10)	0.0096 (9)	0.0068 (9)
C11C	0.0696 (17)	0.0460 (12)	0.0281 (11)	0.0027 (12)	0.0087 (11)	0.0000 (9)
C12C	0.0493 (15)	0.0589 (14)	0.0324 (12)	0.0114 (12)	0.0137 (10)	0.0051 (10)
C5C	0.0349 (12)	0.0369 (11)	0.0338 (11)	0.0107 (10)	0.0091 (9)	0.0102 (9)
C4C	0.0361 (13)	0.0409 (12)	0.0408 (12)	0.0080 (10)	0.0095 (10)	0.0152 (10)
C6C	0.0471 (14)	0.0321 (11)	0.0410 (12)	0.0110 (10)	0.0103 (10)	0.0084 (9)
C7C	0.0509 (14)	0.0332 (11)	0.0342 (12)	0.0050 (10)	0.0098 (10)	−0.0018 (9)
C14C	0.0413 (14)	0.0558 (13)	0.0380 (12)	0.0110 (11)	0.0067 (10)	0.0188 (10)
C13C	0.0546 (15)	0.0448 (12)	0.0338 (12)	0.0089 (11)	0.0082 (11)	0.0097 (9)
C15C	0.0589 (16)	0.0341 (11)	0.0362 (12)	0.0124 (11)	0.0091 (11)	0.0052 (9)
C16C	0.0749 (19)	0.0434 (13)	0.0689 (17)	−0.0002 (13)	0.0129 (14)	0.0143 (12)
C7Y	0.0293 (12)	0.0482 (12)	0.0363 (12)	0.0055 (11)	0.0044 (10)	−0.0001 (10)
C1Y	0.0276 (11)	0.0360 (11)	0.0320 (11)	0.0043 (9)	0.0036 (9)	0.0011 (9)
C6Y	0.0360 (12)	0.0374 (11)	0.0319 (11)	0.0008 (10)	0.0058 (9)	0.0044 (9)
C5Y	0.0365 (12)	0.0352 (10)	0.0349 (12)	−0.0022 (10)	0.0023 (9)	0.0003 (9)
C4Y	0.0362 (12)	0.0361 (11)	0.0309 (11)	0.0087 (10)	0.0056 (9)	0.0017 (9)
C2Y	0.0323 (12)	0.0362 (11)	0.0427 (12)	−0.0026 (10)	0.0039 (10)	0.0014 (9)
C3Y	0.0411 (13)	0.0404 (11)	0.0374 (12)	0.0002 (10)	0.0066 (10)	0.0106 (9)
C7Z	0.0316 (13)	0.0471 (12)	0.0356 (12)	0.0034 (11)	0.0013 (10)	−0.0037 (10)
C1Z	0.0290 (12)	0.0345 (10)	0.0342 (11)	0.0064 (9)	0.0018 (9)	−0.0003 (9)
C2Z	0.0401 (13)	0.0360 (11)	0.0433 (13)	0.0004 (10)	0.0041 (10)	0.0044 (10)
C3Z	0.0478 (14)	0.0466 (12)	0.0334 (12)	0.0050 (11)	0.0014 (10)	0.0112 (10)
C4Z	0.0384 (13)	0.0361 (11)	0.0314 (11)	0.0053 (10)	−0.0021 (9)	0.0005 (9)
C6Z	0.0402 (13)	0.0369 (11)	0.0304 (11)	0.0046 (10)	0.0048 (9)	0.0030 (9)
C5Z	0.0360 (12)	0.0330 (10)	0.0393 (12)	0.0001 (10)	0.0053 (10)	0.0003 (9)

Geometric parameters (Å, º)

F1A—C7A	1.360 (2)	C3B—C2B	1.493 (3)
F1B—C7B	1.353 (2)	C2B—C1B	1.365 (3)
F1C—C7C	1.356 (2)	C2B—C4B	1.424 (3)
O1S—H1A	0.87 (3)	C4B—C5B	1.443 (3)
O1S—H1B	0.92 (3)	C5B—C10B	1.401 (2)
O2A—C3A	1.319 (3)	C5B—C6B	1.406 (3)
O2A—H2	0.925 (16)	C6B—C7B	1.348 (3)
O2S—H2B	0.84 (2)	C6B—H29	0.9300
O2S—H2A	0.89 (3)	C7B—C8B	1.414 (3)
O1A—C3A	1.208 (2)	C8B—C9B	1.381 (2)
O3S—H3A	0.861 (16)	C11B—C12B	1.496 (3)
O3S—H3B	0.87 (3)	C11B—H35	0.9700
O3A—C4A	1.264 (2)	C11B—H34	0.9700
N3B—C12B	1.483 (2)	C12B—H36	0.9700
N3B—C13B	1.486 (2)	C12B—H21	0.9700
N3B—H14B	0.95 (2)	C10B—C9B	1.406 (2)
N3B—H15B	0.91 (2)	C1B—H22	0.9300
O3B—C4B	1.266 (2)	C15B—C16B	1.514 (3)
O1B—C3B	1.203 (3)	C15B—H26	0.9700
O1X—C7X	1.264 (2)	C15B—H27	0.9700
O3X—C4X	1.360 (2)	C16B—H25	0.9600
O3X—H37	0.81 (2)	C16B—H24	0.9600
O2X—C7X	1.253 (2)	C16B—H23	0.9600
O2C—C3C	1.328 (2)	C9B—H28	0.9300
O2C—H42	0.95 (2)	C14B—C13B	1.514 (3)
O1C—C3C	1.209 (2)	C14B—H32	0.9700
O3C—C4C	1.276 (2)	C14B—H33	0.9700
O2Y—C7Y	1.251 (2)	C13B—H31	0.9700
O3Y—C4Y	1.354 (2)	C13B—H30	0.9700
O3Y—H61	0.92 (2)	C7X—C1X	1.495 (3)
O1Y—C7Y	1.261 (2)	C1X—C6X	1.389 (2)
O2Z—C7Z	1.258 (2)	C1X—C2X	1.392 (2)
O3Z—C4Z	1.360 (2)	C2X—C3X	1.377 (3)
O3Z—H66	0.83 (3)	C2X—H41	0.9300
O1Z—C7Z	1.262 (2)	C3X—C4X	1.380 (3)
N3A—C13A	1.476 (2)	C3X—H40	0.9300
N3A—C12A	1.482 (2)	C4X—C5X	1.387 (2)
N3A—H14A	0.9000	C5X—C6X	1.375 (2)
N3A—H15A	0.9000	C5X—H38	0.9300
N2A—C8A	1.402 (2)	C6X—H39	0.9300
N2A—C11A	1.467 (2)	C3C—C2C	1.486 (3)
N2A—C14A	1.468 (2)	C2C—C1C	1.370 (2)
N1A—C1A	1.342 (2)	C2C—C4C	1.414 (3)
N1A—C10A	1.397 (2)	C1C—H60	0.9300
N1A—C15A	1.480 (2)	C10C—C5C	1.403 (2)
O2B—C3B	1.327 (3)	C10C—C9C	1.404 (2)
O2B—H20	0.884 (16)	C9C—C8C	1.378 (2)
N2B—C8B	1.399 (2)	C9C—H53	0.9300
N2B—C14B	1.458 (2)	C8C—C7C	1.418 (2)
N2B—C11B	1.464 (2)	C11C—C12C	1.504 (3)
N1B—C1B	1.340 (2)	C11C—H45	0.9700
N1B—C10B	1.400 (2)	C11C—H46	0.9700
N1B—C15B	1.483 (2)	C12C—H47	0.9700
N1C—C1C	1.343 (2)	C12C—H48	0.9700
N1C—C10C	1.395 (2)	C5C—C6C	1.401 (2)
N1C—C15C	1.481 (2)	C5C—C4C	1.448 (3)
N2C—C8C	1.390 (2)	C6C—C7C	1.350 (3)
N2C—C14C	1.461 (2)	C6C—H54	0.9300
N2C—C11C	1.470 (2)	C14C—C13C	1.505 (3)
N3C—C12C	1.474 (2)	C14C—H52	0.9700
N3C—C13C	1.483 (2)	C14C—H51	0.9700
N3C—H14C	0.9000	C13C—H49	0.9700
N3C—H15C	0.9000	C13C—H50	0.9700
C12A—C11A	1.504 (3)	C15C—C16C	1.512 (3)
C12A—H15	0.9700	C15C—H58	0.9700
C12A—H16	0.9700	C15C—H59	0.9700
C11A—H17	0.9700	C16C—H57	0.9600
C11A—H9	0.9700	C16C—H55	0.9600
C8A—C9A	1.391 (2)	C16C—H56	0.9600
C8A—C7A	1.414 (3)	C7Y—C1Y	1.494 (3)
C9A—C10A	1.399 (2)	C1Y—C6Y	1.383 (3)
C9A—H19	0.9300	C1Y—C2Y	1.389 (2)
C10A—C5A	1.397 (2)	C6Y—C5Y	1.377 (2)
C5A—C6A	1.401 (3)	C6Y—H62	0.9300
C5A—C4A	1.450 (3)	C5Y—C4Y	1.391 (2)
C4A—C2A	1.421 (3)	C5Y—H63	0.9300
C2A—C1A	1.360 (3)	C4Y—C3Y	1.383 (3)
C2A—C3A	1.487 (3)	C2Y—C3Y	1.377 (3)
C15A—C16A	1.501 (4)	C2Y—H65	0.9300
C15A—H6	0.9700	C3Y—H64	0.9300
C15A—H7	0.9700	C7Z—C1Z	1.494 (3)
C16A—H4	0.9600	C1Z—C2Z	1.387 (2)
C16A—H3	0.9600	C1Z—C6Z	1.388 (3)
C16A—H5	0.9600	C2Z—C3Z	1.377 (3)
C1A—H8	0.9300	C2Z—H69	0.9300
C13A—C14A	1.508 (3)	C3Z—C4Z	1.379 (3)
C13A—H14	0.9700	C3Z—H70	0.9300
C13A—H13	0.9700	C4Z—C5Z	1.383 (2)
C14A—H12	0.9700	C6Z—C5Z	1.377 (3)
C14A—H11	0.9700	C6Z—H67	0.9300
C7A—C6A	1.356 (3)	C5Z—H68	0.9300
C6A—H18	0.9300
H1A—O1S—H1B	107 (3)	N1B—C15B—H27	109.4
C3A—O2A—H2	107.4 (15)	C16B—C15B—H27	109.4
H2B—O2S—H2A	109 (3)	H26—C15B—H27	108.0
H3A—O3S—H3B	110 (2)	C15B—C16B—H25	109.5
C12B—N3B—C13B	110.50 (15)	C15B—C16B—H24	109.5
C12B—N3B—H14B	108.3 (12)	H25—C16B—H24	109.5
C13B—N3B—H14B	108.7 (12)	C15B—C16B—H23	109.5
C12B—N3B—H15B	107.4 (12)	H25—C16B—H23	109.5
C13B—N3B—H15B	113.0 (12)	H24—C16B—H23	109.5
H14B—N3B—H15B	108.8 (17)	C8B—C9B—C10B	121.72 (17)
C4X—O3X—H37	112.3 (18)	C8B—C9B—H28	119.1
C3C—O2C—H42	109.2 (15)	C10B—C9B—H28	119.1
C4Y—O3Y—H61	110.1 (14)	N2B—C14B—C13B	113.45 (17)
C4Z—O3Z—H66	112.0 (18)	N2B—C14B—H32	108.9
C13A—N3A—C12A	110.30 (15)	C13B—C14B—H32	108.9
C13A—N3A—H14A	109.6	N2B—C14B—H33	108.9
C12A—N3A—H14A	109.6	C13B—C14B—H33	108.9
C13A—N3A—H15A	109.6	H32—C14B—H33	107.7
C12A—N3A—H15A	109.6	N3B—C13B—C14B	108.80 (16)
H14A—N3A—H15A	108.1	N3B—C13B—H31	109.9
C8A—N2A—C11A	117.89 (16)	C14B—C13B—H31	109.9
C8A—N2A—C14A	116.72 (15)	N3B—C13B—H30	109.9
C11A—N2A—C14A	110.05 (15)	C14B—C13B—H30	109.9
C1A—N1A—C10A	119.41 (16)	H31—C13B—H30	108.3
C1A—N1A—C15A	118.47 (16)	O2X—C7X—O1X	122.22 (18)
C10A—N1A—C15A	122.05 (15)	O2X—C7X—C1X	118.81 (18)
C3B—O2B—H20	111.6 (18)	O1X—C7X—C1X	118.93 (18)
C8B—N2B—C14B	119.44 (15)	C6X—C1X—C2X	118.06 (17)
C8B—N2B—C11B	118.55 (17)	C6X—C1X—C7X	121.40 (17)
C14B—N2B—C11B	111.52 (15)	C2X—C1X—C7X	120.53 (17)
C1B—N1B—C10B	119.82 (16)	C3X—C2X—C1X	121.12 (18)
C1B—N1B—C15B	118.03 (17)	C3X—C2X—H41	119.4
C10B—N1B—C15B	121.98 (15)	C1X—C2X—H41	119.4
C1C—N1C—C10C	119.88 (15)	C2X—C3X—C4X	119.79 (18)
C1C—N1C—C15C	118.37 (16)	C2X—C3X—H40	120.1
C10C—N1C—C15C	121.68 (15)	C4X—C3X—H40	120.1
C8C—N2C—C14C	119.24 (15)	O3X—C4X—C3X	117.46 (18)
C8C—N2C—C11C	118.87 (17)	O3X—C4X—C5X	122.45 (18)
C14C—N2C—C11C	110.05 (15)	C3X—C4X—C5X	120.08 (17)
C12C—N3C—C13C	111.29 (14)	C6X—C5X—C4X	119.63 (18)
C12C—N3C—H14C	109.4	C6X—C5X—H38	120.2
C13C—N3C—H14C	109.4	C4X—C5X—H38	120.2
C12C—N3C—H15C	109.4	C5X—C6X—C1X	121.29 (18)
C13C—N3C—H15C	109.4	C5X—C6X—H39	119.4
H14C—N3C—H15C	108.0	C1X—C6X—H39	119.4
N3A—C12A—C11A	109.92 (18)	O1C—C3C—O2C	121.24 (19)
N3A—C12A—H15	109.7	O1C—C3C—C2C	124.5 (2)
C11A—C12A—H15	109.7	O2C—C3C—C2C	114.2 (2)
N3A—C12A—H16	109.7	C1C—C2C—C4C	119.92 (17)
C11A—C12A—H16	109.7	C1C—C2C—C3C	118.50 (19)
H15—C12A—H16	108.2	C4C—C2C—C3C	121.57 (18)
N2A—C11A—C12A	110.52 (18)	N1C—C1C—C2C	123.68 (18)
N2A—C11A—H17	109.5	N1C—C1C—H60	118.2
C12A—C11A—H17	109.5	C2C—C1C—H60	118.2
N2A—C11A—H9	109.5	N1C—C10C—C5C	119.11 (16)
C12A—C11A—H9	109.5	N1C—C10C—C9C	120.95 (16)
H17—C11A—H9	108.1	C5C—C10C—C9C	119.92 (17)
C9A—C8A—N2A	122.67 (17)	C8C—C9C—C10C	122.00 (17)
C9A—C8A—C7A	115.76 (17)	C8C—C9C—H53	119.0
N2A—C8A—C7A	121.45 (17)	C10C—C9C—H53	119.0
C8A—C9A—C10A	121.86 (17)	C9C—C8C—N2C	123.98 (17)
C8A—C9A—H19	119.1	C9C—C8C—C7C	115.96 (17)
C10A—C9A—H19	119.1	N2C—C8C—C7C	119.95 (17)
C5A—C10A—N1A	119.08 (16)	N2C—C11C—C12C	111.32 (16)
C5A—C10A—C9A	120.57 (17)	N2C—C11C—H45	109.4
N1A—C10A—C9A	120.34 (17)	C12C—C11C—H45	109.4
C10A—C5A—C6A	117.94 (17)	N2C—C11C—H46	109.4
C10A—C5A—C4A	121.39 (17)	C12C—C11C—H46	109.4
C6A—C5A—C4A	120.65 (17)	H45—C11C—H46	108.0
O3A—C4A—C2A	122.96 (18)	N3C—C12C—C11C	110.67 (17)
O3A—C4A—C5A	121.30 (18)	N3C—C12C—H47	109.5
C2A—C4A—C5A	115.74 (17)	C11C—C12C—H47	109.5
C1A—C2A—C4A	120.08 (18)	N3C—C12C—H48	109.5
C1A—C2A—C3A	117.98 (19)	C11C—C12C—H48	109.5
C4A—C2A—C3A	121.94 (19)	H47—C12C—H48	108.1
O1A—C3A—O2A	121.4 (2)	C6C—C5C—C10C	118.40 (17)
O1A—C3A—C2A	123.6 (2)	C6C—C5C—C4C	120.83 (17)
O2A—C3A—C2A	115.1 (2)	C10C—C5C—C4C	120.76 (17)
N1A—C15A—C16A	111.6 (2)	O3C—C4C—C2C	122.69 (17)
N1A—C15A—H6	109.3	O3C—C4C—C5C	120.71 (18)
C16A—C15A—H6	109.3	C2C—C4C—C5C	116.59 (17)
N1A—C15A—H7	109.3	C7C—C6C—C5C	120.05 (17)
C16A—C15A—H7	109.3	C7C—C6C—H54	120.0
H6—C15A—H7	108.0	C5C—C6C—H54	120.0
C15A—C16A—H4	109.5	C6C—C7C—F1C	118.98 (17)
C15A—C16A—H3	109.5	C6C—C7C—C8C	123.51 (18)
H4—C16A—H3	109.5	F1C—C7C—C8C	117.48 (17)
C15A—C16A—H5	109.5	N2C—C14C—C13C	113.52 (17)
H4—C16A—H5	109.5	N2C—C14C—H52	108.9
H3—C16A—H5	109.5	C13C—C14C—H52	108.9
N1A—C1A—C2A	124.28 (19)	N2C—C14C—H51	108.9
N1A—C1A—H8	117.9	C13C—C14C—H51	108.9
C2A—C1A—H8	117.9	H52—C14C—H51	107.7
N3A—C13A—C14A	112.47 (18)	N3C—C13C—C14C	109.75 (16)
N3A—C13A—H14	109.1	N3C—C13C—H49	109.7
C14A—C13A—H14	109.1	C14C—C13C—H49	109.7
N3A—C13A—H13	109.1	N3C—C13C—H50	109.7
C14A—C13A—H13	109.1	C14C—C13C—H50	109.7
H14—C13A—H13	107.8	H49—C13C—H50	108.2
N2A—C14A—C13A	111.54 (16)	N1C—C15C—C16C	111.93 (17)
N2A—C14A—H12	109.3	N1C—C15C—H58	109.2
C13A—C14A—H12	109.3	C16C—C15C—H58	109.2
N2A—C14A—H11	109.3	N1C—C15C—H59	109.2
C13A—C14A—H11	109.3	C16C—C15C—H59	109.2
H12—C14A—H11	108.0	H58—C15C—H59	107.9
C6A—C7A—F1A	117.47 (17)	C15C—C16C—H57	109.5
C6A—C7A—C8A	123.24 (18)	C15C—C16C—H55	109.5
F1A—C7A—C8A	119.24 (17)	H57—C16C—H55	109.5
C7A—C6A—C5A	120.58 (18)	C15C—C16C—H56	109.5
C7A—C6A—H18	119.7	H57—C16C—H56	109.5
C5A—C6A—H18	119.7	H55—C16C—H56	109.5
O1B—C3B—O2B	121.8 (2)	O2Y—C7Y—O1Y	122.51 (19)
O1B—C3B—C2B	124.1 (2)	O2Y—C7Y—C1Y	119.06 (18)
O2B—C3B—C2B	114.1 (2)	O1Y—C7Y—C1Y	118.40 (18)
C1B—C2B—C4B	119.93 (18)	C6Y—C1Y—C2Y	117.90 (17)
C1B—C2B—C3B	118.8 (2)	C6Y—C1Y—C7Y	120.85 (17)
C4B—C2B—C3B	121.28 (19)	C2Y—C1Y—C7Y	121.24 (18)
O3B—C4B—C2B	123.01 (18)	C5Y—C6Y—C1Y	121.41 (18)
O3B—C4B—C5B	121.09 (19)	C5Y—C6Y—H62	119.3
C2B—C4B—C5B	115.90 (17)	C1Y—C6Y—H62	119.3
C10B—C5B—C6B	118.14 (17)	C6Y—C5Y—C4Y	119.98 (18)
C10B—C5B—C4B	121.66 (18)	C6Y—C5Y—H63	120.0
C6B—C5B—C4B	120.20 (17)	C4Y—C5Y—H63	120.0
C7B—C6B—C5B	120.37 (18)	O3Y—C4Y—C3Y	118.34 (17)
C7B—C6B—H29	119.8	O3Y—C4Y—C5Y	122.47 (18)
C5B—C6B—H29	119.8	C3Y—C4Y—C5Y	119.19 (18)
C6B—C7B—F1B	118.72 (17)	C3Y—C2Y—C1Y	121.44 (18)
C6B—C7B—C8B	123.28 (19)	C3Y—C2Y—H65	119.3
F1B—C7B—C8B	117.98 (18)	C1Y—C2Y—H65	119.3
C9B—C8B—N2B	124.24 (17)	C2Y—C3Y—C4Y	120.06 (18)
C9B—C8B—C7B	116.31 (17)	C2Y—C3Y—H64	120.0
N2B—C8B—C7B	119.39 (17)	C4Y—C3Y—H64	120.0
N2B—C11B—C12B	111.72 (16)	O2Z—C7Z—O1Z	123.31 (18)
N2B—C11B—H35	109.3	O2Z—C7Z—C1Z	118.54 (19)
C12B—C11B—H35	109.3	O1Z—C7Z—C1Z	118.10 (18)
N2B—C11B—H34	109.3	C2Z—C1Z—C6Z	117.91 (17)
C12B—C11B—H34	109.3	C2Z—C1Z—C7Z	121.39 (18)
H35—C11B—H34	107.9	C6Z—C1Z—C7Z	120.68 (17)
N3B—C12B—C11B	110.03 (18)	C3Z—C2Z—C1Z	121.63 (19)
N3B—C12B—H36	109.7	C3Z—C2Z—H69	119.2
C11B—C12B—H36	109.7	C1Z—C2Z—H69	119.2
N3B—C12B—H21	109.7	C2Z—C3Z—C4Z	119.49 (18)
C11B—C12B—H21	109.7	C2Z—C3Z—H70	120.3
H36—C12B—H21	108.2	C4Z—C3Z—H70	120.3
N1B—C10B—C5B	118.62 (16)	O3Z—C4Z—C3Z	117.93 (18)
N1B—C10B—C9B	121.28 (17)	O3Z—C4Z—C5Z	122.10 (18)
C5B—C10B—C9B	120.09 (17)	C3Z—C4Z—C5Z	119.96 (18)
N1B—C1B—C2B	124.05 (19)	C5Z—C6Z—C1Z	121.02 (18)
N1B—C1B—H22	118.0	C5Z—C6Z—H67	119.5
C2B—C1B—H22	118.0	C1Z—C6Z—H67	119.5
N1B—C15B—C16B	110.99 (18)	C6Z—C5Z—C4Z	119.98 (18)
N1B—C15B—H26	109.4	C6Z—C5Z—H68	120.0
C16B—C15B—H26	109.4	C4Z—C5Z—H68	120.0
C13A—N3A—C12A—C11A	56.6 (2)	C8B—N2B—C14B—C13B	91.2 (2)
C8A—N2A—C11A—C12A	−163.13 (18)	C11B—N2B—C14B—C13B	−53.2 (2)
C14A—N2A—C11A—C12A	59.6 (2)	C12B—N3B—C13B—C14B	−57.3 (2)
N3A—C12A—C11A—N2A	−60.5 (2)	N2B—C14B—C13B—N3B	54.7 (2)
C11A—N2A—C8A—C9A	−134.2 (2)	O2X—C7X—C1X—C6X	−168.34 (18)
C14A—N2A—C8A—C9A	0.3 (3)	O1X—C7X—C1X—C6X	14.0 (3)
C11A—N2A—C8A—C7A	50.0 (3)	O2X—C7X—C1X—C2X	12.7 (3)
C14A—N2A—C8A—C7A	−175.53 (19)	O1X—C7X—C1X—C2X	−165.03 (18)
N2A—C8A—C9A—C10A	−174.86 (18)	C6X—C1X—C2X—C3X	−1.6 (3)
C7A—C8A—C9A—C10A	1.2 (3)	C7X—C1X—C2X—C3X	177.45 (18)
C1A—N1A—C10A—C5A	0.3 (3)	C1X—C2X—C3X—C4X	0.9 (3)
C15A—N1A—C10A—C5A	−176.6 (2)	C2X—C3X—C4X—O3X	−178.67 (18)
C1A—N1A—C10A—C9A	−179.07 (19)	C2X—C3X—C4X—C5X	0.6 (3)
C15A—N1A—C10A—C9A	4.0 (3)	O3X—C4X—C5X—C6X	177.95 (18)
C8A—C9A—C10A—C5A	−2.4 (3)	C3X—C4X—C5X—C6X	−1.3 (3)
C8A—C9A—C10A—N1A	176.96 (18)	C4X—C5X—C6X—C1X	0.5 (3)
N1A—C10A—C5A—C6A	−177.97 (18)	C2X—C1X—C6X—C5X	0.9 (3)
C9A—C10A—C5A—C6A	1.4 (3)	C7X—C1X—C6X—C5X	−178.14 (18)
N1A—C10A—C5A—C4A	0.2 (3)	O1C—C3C—C2C—C1C	0.8 (3)
C9A—C10A—C5A—C4A	179.52 (18)	O2C—C3C—C2C—C1C	−179.46 (18)
C10A—C5A—C4A—O3A	179.8 (2)	O1C—C3C—C2C—C4C	−179.1 (2)
C6A—C5A—C4A—O3A	−2.1 (3)	O2C—C3C—C2C—C4C	0.6 (3)
C10A—C5A—C4A—C2A	−1.2 (3)	C10C—N1C—C1C—C2C	2.1 (3)
C6A—C5A—C4A—C2A	176.87 (19)	C15C—N1C—C1C—C2C	178.95 (18)
O3A—C4A—C2A—C1A	−179.2 (2)	C4C—C2C—C1C—N1C	−0.4 (3)
C5A—C4A—C2A—C1A	1.9 (3)	C3C—C2C—C1C—N1C	179.67 (19)
O3A—C4A—C2A—C3A	1.7 (3)	C1C—N1C—C10C—C5C	−2.1 (3)
C5A—C4A—C2A—C3A	−177.22 (19)	C15C—N1C—C10C—C5C	−178.74 (18)
C1A—C2A—C3A—O1A	−2.6 (4)	C1C—N1C—C10C—C9C	176.77 (18)
C4A—C2A—C3A—O1A	176.6 (2)	C15C—N1C—C10C—C9C	0.1 (3)
C1A—C2A—C3A—O2A	178.1 (2)	N1C—C10C—C9C—C8C	−177.52 (17)
C4A—C2A—C3A—O2A	−2.8 (3)	C5C—C10C—C9C—C8C	1.3 (3)
C1A—N1A—C15A—C16A	−96.5 (2)	C10C—C9C—C8C—N2C	179.93 (18)
C10A—N1A—C15A—C16A	80.4 (3)	C10C—C9C—C8C—C7C	−3.9 (3)
C10A—N1A—C1A—C2A	0.4 (3)	C14C—N2C—C8C—C9C	10.7 (3)
C15A—N1A—C1A—C2A	177.5 (2)	C11C—N2C—C8C—C9C	−128.5 (2)
C4A—C2A—C1A—N1A	−1.6 (3)	C14C—N2C—C8C—C7C	−165.28 (18)
C3A—C2A—C1A—N1A	177.6 (2)	C11C—N2C—C8C—C7C	55.5 (3)
C12A—N3A—C13A—C14A	−53.4 (2)	C8C—N2C—C11C—C12C	86.9 (2)
C8A—N2A—C14A—C13A	166.66 (17)	C14C—N2C—C11C—C12C	−55.8 (2)
C11A—N2A—C14A—C13A	−55.5 (2)	C13C—N3C—C12C—C11C	−56.7 (2)
N3A—C13A—C14A—N2A	53.2 (2)	N2C—C11C—C12C—N3C	57.3 (2)
C9A—C8A—C7A—C6A	1.0 (3)	N1C—C10C—C5C—C6C	−179.49 (17)
N2A—C8A—C7A—C6A	177.06 (19)	C9C—C10C—C5C—C6C	1.7 (3)
C9A—C8A—C7A—F1A	−176.37 (18)	N1C—C10C—C5C—C4C	0.3 (3)
N2A—C8A—C7A—F1A	−0.3 (3)	C9C—C10C—C5C—C4C	−178.53 (18)
F1A—C7A—C6A—C5A	175.44 (18)	C1C—C2C—C4C—O3C	178.71 (19)
C8A—C7A—C6A—C5A	−1.9 (3)	C3C—C2C—C4C—O3C	−1.3 (3)
C10A—C5A—C6A—C7A	0.7 (3)	C1C—C2C—C4C—C5C	−1.4 (3)
C4A—C5A—C6A—C7A	−177.45 (19)	C3C—C2C—C4C—C5C	178.60 (18)
O1B—C3B—C2B—C1B	−1.6 (4)	C6C—C5C—C4C—O3C	1.1 (3)
O2B—C3B—C2B—C1B	179.0 (2)	C10C—C5C—C4C—O3C	−178.70 (18)
O1B—C3B—C2B—C4B	178.1 (2)	C6C—C5C—C4C—C2C	−178.85 (18)
O2B—C3B—C2B—C4B	−1.3 (3)	C10C—C5C—C4C—C2C	1.4 (3)
C1B—C2B—C4B—O3B	−179.5 (2)	C10C—C5C—C6C—C7C	−1.7 (3)
C3B—C2B—C4B—O3B	0.9 (3)	C4C—C5C—C6C—C7C	178.46 (19)
C1B—C2B—C4B—C5B	0.3 (3)	C5C—C6C—C7C—F1C	176.88 (18)
C3B—C2B—C4B—C5B	−179.39 (19)	C5C—C6C—C7C—C8C	−1.1 (3)
O3B—C4B—C5B—C10B	179.17 (19)	C9C—C8C—C7C—C6C	3.9 (3)
C2B—C4B—C5B—C10B	−0.6 (3)	N2C—C8C—C7C—C6C	−179.76 (19)
O3B—C4B—C5B—C6B	−0.4 (3)	C9C—C8C—C7C—F1C	−174.10 (17)
C2B—C4B—C5B—C6B	179.83 (18)	N2C—C8C—C7C—F1C	2.2 (3)
C10B—C5B—C6B—C7B	1.5 (3)	C8C—N2C—C14C—C13C	−87.1 (2)
C4B—C5B—C6B—C7B	−178.9 (2)	C11C—N2C—C14C—C13C	55.4 (2)
C5B—C6B—C7B—F1B	−177.07 (18)	C12C—N3C—C13C—C14C	54.6 (2)
C5B—C6B—C7B—C8B	1.1 (3)	N2C—C14C—C13C—N3C	−54.7 (2)
C14B—N2B—C8B—C9B	−14.3 (3)	C1C—N1C—C15C—C16C	−97.0 (2)
C11B—N2B—C8B—C9B	127.6 (2)	C10C—N1C—C15C—C16C	79.7 (2)
C14B—N2B—C8B—C7B	162.79 (18)	O2Y—C7Y—C1Y—C6Y	174.64 (18)
C11B—N2B—C8B—C7B	−55.3 (3)	O1Y—C7Y—C1Y—C6Y	−7.2 (3)
C6B—C7B—C8B—C9B	−3.2 (3)	O2Y—C7Y—C1Y—C2Y	−6.3 (3)
F1B—C7B—C8B—C9B	175.00 (18)	O1Y—C7Y—C1Y—C2Y	171.87 (18)
C6B—C7B—C8B—N2B	179.5 (2)	C2Y—C1Y—C6Y—C5Y	−0.9 (3)
F1B—C7B—C8B—N2B	−2.3 (3)	C7Y—C1Y—C6Y—C5Y	178.25 (17)
C8B—N2B—C11B—C12B	−91.0 (2)	C1Y—C6Y—C5Y—C4Y	0.6 (3)
C14B—N2B—C11B—C12B	53.7 (2)	C6Y—C5Y—C4Y—O3Y	−179.85 (18)
C13B—N3B—C12B—C11B	59.6 (2)	C6Y—C5Y—C4Y—C3Y	−0.5 (3)
N2B—C11B—C12B—N3B	−57.2 (2)	C6Y—C1Y—C2Y—C3Y	1.1 (3)
C1B—N1B—C10B—C5B	1.4 (3)	C7Y—C1Y—C2Y—C3Y	−178.03 (18)
C15B—N1B—C10B—C5B	176.48 (19)	C1Y—C2Y—C3Y—C4Y	−1.0 (3)
C1B—N1B—C10B—C9B	−177.29 (19)	O3Y—C4Y—C3Y—C2Y	−179.91 (18)
C15B—N1B—C10B—C9B	−2.2 (3)	C5Y—C4Y—C3Y—C2Y	0.7 (3)
C6B—C5B—C10B—N1B	179.38 (17)	O2Z—C7Z—C1Z—C2Z	−8.4 (3)
C4B—C5B—C10B—N1B	−0.2 (3)	O1Z—C7Z—C1Z—C2Z	169.21 (18)
C6B—C5B—C10B—C9B	−2.0 (3)	O2Z—C7Z—C1Z—C6Z	172.90 (18)
C4B—C5B—C10B—C9B	178.46 (18)	O1Z—C7Z—C1Z—C6Z	−9.5 (3)
C10B—N1B—C1B—C2B	−1.8 (3)	C6Z—C1Z—C2Z—C3Z	0.9 (3)
C15B—N1B—C1B—C2B	−177.1 (2)	C7Z—C1Z—C2Z—C3Z	−177.87 (19)
C4B—C2B—C1B—N1B	0.9 (3)	C1Z—C2Z—C3Z—C4Z	−0.8 (3)
C3B—C2B—C1B—N1B	−179.42 (19)	C2Z—C3Z—C4Z—O3Z	179.33 (18)
C1B—N1B—C15B—C16B	95.0 (2)	C2Z—C3Z—C4Z—C5Z	0.4 (3)
C10B—N1B—C15B—C16B	−80.2 (2)	C2Z—C1Z—C6Z—C5Z	−0.5 (3)
N2B—C8B—C9B—C10B	179.85 (18)	C7Z—C1Z—C6Z—C5Z	178.22 (18)
C7B—C8B—C9B—C10B	2.7 (3)	C1Z—C6Z—C5Z—C4Z	0.2 (3)
N1B—C10B—C9B—C8B	178.42 (17)	O3Z—C4Z—C5Z—C6Z	−178.97 (18)
C5B—C10B—C9B—C8B	−0.2 (3)	C3Z—C4Z—C5Z—C6Z	−0.1 (3)