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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520614011718/og5069sup1.cif
Contains datablocks 20120152_0m, 20120156_0m, 20120175_0m, 2013130_0m, 2013176_0ma, 2013329_0m, mo_2014070_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og506920120152_0msup2.hkl
Contains datablock 20120152_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og506920120156_0msup3.hkl
Contains datablock 20120156_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og506920120175_0msup4.hkl
Contains datablock 20120175_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og50692013130_0msup5.hkl
Contains datablock 2013130_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og50692013176_0masup6.hkl
Contains datablock 2013176_0ma

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og50692013329_0msup7.hkl
Contains datablock 2013329_0m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520614011718/og5069mo_2014070_0msup8.hkl
Contains datablock mo_2014070_0m

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520614011718/og5069sup9.pdf
Physical characterization such as PXRD, TG, DSC, HSM

CCDC references: 1004351; 1004352; 1004353; 1004354; 1004355; 1004356; 1004357

Experimental top

Refinement top

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

Results and discussion top

Computing details top

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 top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
[Figure 12]
(20120152_0m) top
Crystal data top
C44H56F2N6O14V = 2255.11 (11) Å3
Mr = 930.95Z = 2
Triclinic, P1F(000) = 984.0
a = 9.4994 (3) ÅDx = 1.371 Mg m3
b = 14.3694 (4) ÅMo Kα radiation, λ = 0.71073 Å
c = 18.1458 (5) ŵ = 0.11 mm1
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 top
CCD area detector
diffractometer
5556 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
phi and ω scansh = 1111
31371 measured reflectionsk = 1717
7942 independent reflectionsl = 2021
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 0.99 w = 1/[σ2(Fo2) + (0.0607P)2 + 1.0643P]
where P = (Fo2 + 2Fc2)/3
7942 reflections(Δ/σ)max = 0.001
633 parametersΔρmax = 0.68 e Å3
164 restraintsΔρmin = 0.19 e Å3
Crystal data top
C44H56F2N6O14γ = 106.946 (2)°
Mr = 930.95V = 2255.11 (11) Å3
Triclinic, P1Z = 2
a = 9.4994 (3) ÅMo Kα radiation
b = 14.3694 (4) ŵ = 0.11 mm1
c = 18.1458 (5) ÅT = 100 K
α = 103.853 (1)°0.31 × 0.23 × 0.15 mm
β = 96.528 (1)°
Data collection top
CCD area detector
diffractometer
5556 reflections with I > 2σ(I)
31371 measured reflectionsRint = 0.030
7942 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045164 restraints
wR(F2) = 0.132H atoms treated by a mixture of independent and constrained refinement
S = 0.99Δρmax = 0.68 e Å3
7942 reflectionsΔρmin = 0.19 e Å3
633 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O3Y0.09506 (16)0.71691 (11)0.55069 (8)0.0386 (4)
O1Y0.40092 (16)0.29493 (11)0.47177 (9)0.0405 (4)
O4X0.55392 (17)0.17700 (11)0.45828 (9)0.0400 (4)
H10'0.495 (3)0.219 (2)0.4646 (15)0.060*
O3X0.5423 (2)0.18818 (15)0.58111 (10)0.0655 (5)
O1X0.9071 (2)0.18355 (14)0.68179 (10)0.0589 (5)
O1A0.3670 (2)0.86399 (16)1.12710 (11)0.0738 (6)
O2A0.1405 (2)0.94601 (15)1.19827 (10)0.0608 (5)
O3A0.0877 (2)0.96134 (14)1.13573 (9)0.0566 (5)
F1A0.41171 (15)0.91658 (12)0.93795 (8)0.0671 (5)
N3A0.3352 (2)0.73711 (14)0.66485 (10)0.0348 (4)
O2B1.1294 (3)0.54982 (18)0.15755 (12)0.0879 (7)
H281.04360.53450.14950.132*
O1B1.3554 (3)0.6509 (2)0.09273 (14)0.1025 (8)
O3B0.9041 (3)0.53883 (15)0.09410 (10)0.0733 (6)
F1B0.58306 (16)0.58257 (12)0.10412 (8)0.0650 (4)
N3B0.7313 (2)0.69798 (15)0.39929 (11)0.0382 (4)
O4Y0.03338 (19)0.63743 (14)0.43068 (9)0.0574 (5)
N2A0.22813 (19)0.80111 (13)0.80036 (10)0.0381 (4)
N1A0.1982 (2)0.80455 (15)0.92662 (10)0.0445 (5)
C5A0.0559 (2)0.88715 (16)1.00071 (12)0.0361 (5)
N2B0.76965 (19)0.69207 (13)0.24427 (10)0.0367 (4)
C1Y0.3975 (2)0.35251 (15)0.42878 (12)0.0315 (5)
O2Y0.47495 (18)0.36090 (13)0.37836 (9)0.0487 (4)
C1X0.9029 (2)0.13542 (16)0.63617 (13)0.0375 (5)
C2X0.8266 (3)0.05630 (17)0.64539 (13)0.0411 (5)
H3'0.88420.00010.69010.049*
H2'0.72860.08520.65680.049*
C3X0.8053 (2)0.01472 (16)0.57773 (13)0.0378 (5)
H5'0.75160.07070.53200.045*
H4'0.90300.01890.56810.045*
C4X0.7192 (2)0.06014 (16)0.59084 (13)0.0373 (5)
H7'0.62450.02840.60430.045*
H6'0.77660.11890.63390.045*
C5X0.6891 (2)0.09420 (17)0.51948 (14)0.0414 (5)
H9'0.78440.13240.51000.050*
H8'0.64400.03440.47540.050*
C6X0.5890 (2)0.15817 (15)0.52413 (13)0.0357 (5)
C13A0.2463 (2)0.66372 (16)0.70165 (12)0.0359 (5)
H170.31310.65050.73930.043*
H160.19080.60000.66260.043*
C14A0.1389 (2)0.70741 (16)0.74096 (12)0.0348 (5)
H180.07220.72130.70370.042*
H190.07860.65970.76420.042*
C8A0.1659 (2)0.83386 (16)0.86427 (12)0.0365 (5)
C9A0.0135 (2)0.80628 (17)0.86212 (12)0.0385 (5)
H30.05280.77010.81530.046*
C10A0.0433 (2)0.83194 (16)0.92947 (12)0.0367 (5)
C1A0.2492 (3)0.82580 (19)0.99254 (13)0.0468 (6)
H10.35250.80540.98940.056*
C2A0.1595 (3)0.87527 (17)1.06383 (13)0.0409 (5)
C3A0.2331 (3)0.89331 (19)1.13152 (14)0.0491 (6)
C15A0.3073 (3)0.7540 (2)0.85188 (14)0.0598 (7)
H50.26760.78270.81230.072*
H40.40030.76780.85710.072*
C16A0.3395 (3)0.6422 (2)0.82674 (17)0.0749 (9)
H80.24700.62800.82530.112*
H70.40230.61400.77610.112*
H60.39000.61240.86260.112*
C4A0.0005 (3)0.91138 (16)1.07162 (12)0.0392 (5)
C6A0.2109 (3)0.91721 (17)1.00194 (13)0.0426 (5)
H20.27840.95491.04810.051*
C7A0.2621 (2)0.89129 (17)0.93584 (13)0.0422 (5)
C11A0.3110 (2)0.87789 (16)0.76618 (13)0.0407 (5)
H100.36780.93980.80680.049*
H110.24120.89350.73170.049*
C12A0.4164 (2)0.83817 (17)0.72167 (13)0.0416 (5)
H130.46300.88580.69450.050*
H120.49520.83240.75750.050*
C13B0.7843 (3)0.79221 (17)0.37611 (13)0.0430 (5)
H360.85040.84680.41990.052*
H350.69940.81190.35950.052*
C14B0.8677 (2)0.77425 (17)0.31048 (12)0.0401 (5)
H370.90270.83590.29510.048*
H380.95460.75690.32790.048*
C8B0.8290 (2)0.67663 (16)0.17582 (12)0.0362 (5)
C7B0.7320 (3)0.61764 (18)0.10489 (13)0.0441 (5)
C6B0.7821 (3)0.59406 (18)0.03778 (13)0.0486 (6)
H210.71420.55380.00770.058*
C5B0.9356 (3)0.63027 (17)0.03707 (13)0.0443 (5)
C4B0.9926 (3)0.59992 (19)0.03296 (14)0.0538 (6)
C2B1.1498 (4)0.6410 (2)0.02720 (15)0.0581 (7)
C3B1.2223 (5)0.6152 (3)0.09452 (19)0.0739 (9)
C11B0.7143 (3)0.59792 (17)0.26671 (13)0.0420 (5)
H300.79830.57670.28220.050*
H290.64720.54450.22260.050*
C12B0.6321 (2)0.61347 (18)0.33270 (13)0.0436 (5)
H310.54300.62890.31600.052*
H320.60070.55170.34820.052*
C9B0.9790 (2)0.71591 (17)0.17440 (13)0.0395 (5)
H221.04550.75830.21980.047*
C10B1.0339 (3)0.69334 (17)0.10583 (13)0.0423 (5)
N1B1.1872 (2)0.73114 (17)0.10611 (12)0.0537 (5)
C1B1.2380 (3)0.7033 (2)0.04093 (16)0.0611 (7)
H201.34070.72870.04280.073*
C15B1.2969 (3)0.7930 (3)0.17795 (19)0.0781 (9)
C16B1.3397 (5)0.7303 (4)0.2236 (2)0.1274 (17)
H251.25110.68640.23380.191*
H271.40440.77350.27170.191*
H261.39140.69010.19510.191*
C6Y0.0700 (2)0.65237 (15)0.48522 (12)0.0325 (5)
C5Y0.1726 (2)0.58944 (16)0.47490 (13)0.0381 (5)
H18'0.27550.63530.48990.046*
H17'0.15870.54840.51050.046*
C4Y0.1533 (3)0.5205 (2)0.39554 (13)0.0502 (6)
H16'0.15100.55870.35820.060*
H15'0.05740.46660.38360.060*
C3Y0.2769 (3)0.4734 (2)0.38662 (14)0.0495 (6)
H13'0.25660.42960.33410.059*
H14'0.37170.52710.39430.059*
C2Y0.2920 (2)0.41288 (16)0.44189 (13)0.0363 (5)
H11'0.19320.36630.43950.044*
H12'0.32560.45900.49390.044*
H140.404 (2)0.7100 (18)0.6451 (14)0.057 (7)*
H330.683 (2)0.7060 (17)0.4396 (11)0.047 (7)*
H150.270 (2)0.7407 (17)0.6252 (11)0.050 (7)*
H231.267 (3)0.856 (2)0.2092 (19)0.089 (10)*
H90.048 (4)0.961 (3)1.186 (2)0.102 (13)*
O2X0.96215 (19)0.14786 (13)0.57354 (10)0.0499 (4)
H241.383 (4)0.843 (3)0.161 (2)0.106 (11)*
H340.811 (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 (Å2) top
U11U22U33U12U13U23
O3Y0.0398 (8)0.0422 (8)0.0398 (8)0.0243 (7)0.0104 (7)0.0083 (7)
O1Y0.0471 (9)0.0490 (9)0.0448 (9)0.0315 (7)0.0214 (7)0.0235 (8)
O4X0.0442 (9)0.0461 (9)0.0451 (9)0.0275 (7)0.0179 (7)0.0211 (7)
O3X0.0963 (14)0.0898 (14)0.0465 (10)0.0696 (12)0.0314 (10)0.0292 (10)
O1X0.0848 (13)0.0687 (12)0.0478 (10)0.0512 (10)0.0165 (9)0.0278 (9)
O1A0.0676 (12)0.0929 (15)0.0615 (12)0.0251 (11)0.0404 (10)0.0122 (11)
O2A0.0787 (13)0.0746 (13)0.0375 (10)0.0355 (11)0.0274 (10)0.0112 (9)
O3A0.0649 (11)0.0677 (11)0.0320 (9)0.0231 (9)0.0137 (8)0.0015 (8)
F1A0.0380 (7)0.0846 (11)0.0528 (9)0.0027 (7)0.0143 (7)0.0083 (8)
N3A0.0361 (10)0.0476 (11)0.0316 (10)0.0252 (8)0.0144 (8)0.0138 (8)
O2B0.168 (2)0.0890 (16)0.0523 (12)0.0826 (16)0.0615 (14)0.0359 (11)
O1B0.134 (2)0.134 (2)0.0920 (17)0.0791 (17)0.0860 (16)0.0548 (16)
O3B0.1195 (17)0.0771 (13)0.0344 (10)0.0504 (12)0.0222 (11)0.0108 (9)
F1B0.0489 (8)0.0864 (11)0.0452 (8)0.0089 (8)0.0041 (7)0.0111 (8)
N3B0.0390 (10)0.0569 (12)0.0326 (10)0.0266 (9)0.0179 (9)0.0197 (9)
O4Y0.0564 (10)0.0862 (13)0.0416 (9)0.0512 (10)0.0032 (8)0.0090 (9)
N2A0.0417 (10)0.0391 (10)0.0329 (10)0.0117 (8)0.0181 (8)0.0062 (8)
N1A0.0407 (10)0.0651 (13)0.0324 (10)0.0230 (9)0.0135 (8)0.0129 (9)
C5A0.0462 (12)0.0357 (11)0.0316 (11)0.0174 (9)0.0146 (9)0.0111 (9)
N2B0.0409 (10)0.0400 (10)0.0293 (9)0.0112 (8)0.0119 (8)0.0108 (8)
C1Y0.0311 (10)0.0328 (11)0.0347 (11)0.0161 (9)0.0106 (9)0.0082 (9)
O2Y0.0560 (10)0.0672 (11)0.0537 (10)0.0440 (9)0.0362 (8)0.0325 (9)
C1X0.0367 (12)0.0401 (12)0.0377 (12)0.0178 (10)0.0030 (10)0.0105 (10)
C2X0.0469 (13)0.0443 (13)0.0377 (12)0.0250 (11)0.0067 (10)0.0105 (10)
C3X0.0346 (11)0.0386 (12)0.0452 (13)0.0179 (9)0.0091 (10)0.0137 (10)
C4X0.0371 (11)0.0360 (11)0.0414 (12)0.0175 (9)0.0064 (10)0.0097 (10)
C5X0.0430 (12)0.0432 (13)0.0528 (14)0.0243 (10)0.0194 (11)0.0234 (11)
C6X0.0386 (12)0.0340 (11)0.0419 (12)0.0160 (9)0.0141 (10)0.0163 (10)
C13A0.0412 (12)0.0393 (12)0.0341 (11)0.0202 (10)0.0121 (10)0.0122 (9)
C14A0.0367 (11)0.0385 (11)0.0321 (11)0.0150 (9)0.0124 (9)0.0097 (9)
C8A0.0437 (12)0.0377 (12)0.0316 (11)0.0152 (10)0.0157 (9)0.0102 (9)
C9A0.0408 (11)0.0486 (13)0.0283 (11)0.0175 (10)0.0104 (9)0.0098 (10)
C10A0.0397 (11)0.0451 (12)0.0320 (11)0.0193 (10)0.0139 (9)0.0138 (10)
C1A0.0467 (13)0.0605 (15)0.0437 (13)0.0257 (12)0.0229 (11)0.0176 (12)
C2A0.0549 (13)0.0445 (13)0.0351 (11)0.0259 (11)0.0210 (10)0.0156 (10)
C3A0.0654 (16)0.0524 (15)0.0434 (14)0.0296 (13)0.0290 (12)0.0179 (12)
C15A0.0427 (13)0.099 (2)0.0430 (14)0.0317 (14)0.0127 (11)0.0186 (14)
C16A0.0550 (17)0.098 (2)0.0539 (17)0.0156 (16)0.0081 (14)0.0023 (16)
C4A0.0553 (13)0.0391 (12)0.0317 (11)0.0234 (10)0.0161 (10)0.0122 (10)
C6A0.0460 (12)0.0427 (13)0.0319 (12)0.0111 (10)0.0082 (10)0.0020 (10)
C7A0.0362 (11)0.0450 (13)0.0404 (12)0.0103 (10)0.0138 (10)0.0040 (10)
C11A0.0447 (13)0.0387 (12)0.0413 (13)0.0135 (10)0.0206 (10)0.0109 (10)
C12A0.0381 (12)0.0486 (13)0.0390 (12)0.0139 (10)0.0150 (10)0.0115 (10)
C13B0.0487 (13)0.0466 (13)0.0380 (12)0.0192 (11)0.0166 (11)0.0118 (10)
C14B0.0439 (12)0.0412 (12)0.0344 (12)0.0107 (10)0.0153 (10)0.0100 (10)
C8B0.0462 (12)0.0395 (12)0.0291 (10)0.0182 (10)0.0139 (9)0.0130 (9)
C7B0.0464 (13)0.0494 (14)0.0360 (12)0.0139 (11)0.0081 (10)0.0139 (11)
C6B0.0698 (15)0.0480 (14)0.0281 (11)0.0206 (12)0.0076 (11)0.0106 (10)
C5B0.0694 (15)0.0468 (13)0.0316 (11)0.0316 (12)0.0205 (11)0.0184 (10)
C4B0.1001 (18)0.0531 (15)0.0330 (13)0.0476 (14)0.0274 (13)0.0232 (11)
C2B0.0940 (18)0.0654 (17)0.0479 (14)0.0512 (15)0.0435 (14)0.0321 (13)
C3B0.131 (3)0.081 (2)0.0607 (18)0.074 (2)0.0608 (19)0.0461 (16)
C11B0.0470 (13)0.0407 (12)0.0365 (12)0.0089 (10)0.0135 (10)0.0122 (10)
C12B0.0375 (12)0.0525 (14)0.0434 (13)0.0111 (10)0.0146 (10)0.0201 (11)
C9B0.0453 (12)0.0443 (13)0.0308 (11)0.0155 (10)0.0142 (10)0.0103 (10)
C10B0.0536 (13)0.0470 (13)0.0385 (12)0.0245 (11)0.0212 (10)0.0190 (10)
N1B0.0564 (12)0.0713 (14)0.0447 (11)0.0272 (11)0.0292 (10)0.0207 (10)
C1B0.0771 (18)0.0778 (19)0.0566 (15)0.0426 (15)0.0435 (14)0.0352 (14)
C15B0.0486 (16)0.119 (3)0.0584 (18)0.0184 (17)0.0240 (14)0.0148 (18)
C16B0.116 (3)0.226 (5)0.065 (2)0.105 (4)0.009 (2)0.033 (3)
C6Y0.0308 (10)0.0377 (11)0.0381 (12)0.0175 (9)0.0135 (9)0.0165 (10)
C5Y0.0325 (11)0.0362 (12)0.0463 (13)0.0185 (9)0.0055 (10)0.0057 (10)
C4Y0.0651 (16)0.0664 (16)0.0365 (12)0.0480 (14)0.0117 (12)0.0130 (12)
C3Y0.0675 (16)0.0664 (16)0.0427 (13)0.0496 (14)0.0272 (12)0.0251 (12)
C2Y0.0365 (11)0.0385 (12)0.0438 (12)0.0215 (9)0.0188 (10)0.0137 (10)
O2X0.0578 (10)0.0560 (10)0.0596 (11)0.0396 (9)0.0257 (9)0.0278 (9)
Geometric parameters (Å, º) top
O3Y—C6Y1.268 (2)C1A—C2A1.364 (3)
O1Y—C1Y1.270 (2)C1A—H10.9300
O4X—C6X1.315 (3)C2A—C4A1.425 (3)
O4X—H10'0.93 (3)C2A—C3A1.487 (3)
O3X—C6X1.206 (3)C15A—C16A1.488 (4)
O1X—C1X1.203 (3)C15A—H50.9700
O1A—C3A1.204 (3)C15A—H40.9700
O2A—C3A1.321 (3)C16A—H80.9600
O2A—H90.91 (4)C16A—H70.9600
O3A—C4A1.264 (3)C16A—H60.9600
F1A—C7A1.354 (2)C6A—C7A1.356 (3)
N3A—C12A1.489 (3)C6A—H20.9300
N3A—C13A1.489 (3)C11A—C12A1.509 (3)
N3A—H140.918 (17)C11A—H100.9700
N3A—H150.914 (16)C11A—H110.9700
O2B—C3B1.320 (4)C12A—H130.9700
O2B—H280.8200C12A—H120.9700
O1B—C3B1.211 (4)C13B—C14B1.516 (3)
O3B—C4B1.265 (3)C13B—H360.9700
F1B—C7B1.354 (3)C13B—H350.9700
N3B—C13B1.479 (3)C14B—H370.9700
N3B—C12B1.481 (3)C14B—H380.9700
N3B—H330.906 (16)C8B—C9B1.377 (3)
N3B—H340.917 (16)C8B—C7B1.406 (3)
O4Y—C6Y1.243 (2)C7B—C6B1.361 (3)
N2A—C8A1.404 (3)C6B—C5B1.401 (3)
N2A—C14A1.458 (3)C6B—H210.9300
N2A—C11A1.468 (3)C5B—C10B1.396 (3)
N1A—C1A1.342 (3)C5B—C4B1.459 (3)
N1A—C10A1.400 (3)C4B—C2B1.417 (4)
N1A—C15A1.487 (3)C2B—C1B1.353 (4)
C5A—C6A1.404 (3)C2B—C3B1.492 (4)
C5A—C10A1.409 (3)C11B—C12B1.510 (3)
C5A—C4A1.455 (3)C11B—H300.9700
N2B—C8B1.418 (3)C11B—H290.9700
N2B—C14B1.460 (3)C12B—H310.9700
N2B—C11B1.473 (3)C12B—H320.9700
C1Y—O2Y1.243 (2)C9B—C10B1.406 (3)
C1Y—C2Y1.509 (3)C9B—H220.9300
C1X—O2X1.322 (3)C10B—N1B1.397 (3)
C1X—C2X1.505 (3)N1B—C1B1.345 (3)
C2X—C3X1.507 (3)N1B—C15B1.474 (4)
C2X—H3'0.9700C1B—H200.9300
C2X—H2'0.9700C15B—C16B1.468 (5)
C3X—C4X1.522 (3)C15B—H231.08 (3)
C3X—H5'0.9700C15B—H241.06 (4)
C3X—H4'0.9700C16B—H250.9600
C4X—C5X1.516 (3)C16B—H270.9600
C4X—H7'0.9700C16B—H260.9600
C4X—H6'0.9700C6Y—C5Y1.509 (3)
C5X—C6X1.500 (3)C5Y—C4Y1.496 (3)
C5X—H9'0.9700C5Y—H18'0.9700
C5X—H8'0.9700C5Y—H17'0.9700
C13A—C14A1.506 (3)C4Y—C3Y1.522 (3)
C13A—H170.9700C4Y—H16'0.9700
C13A—H160.9700C4Y—H15'0.9700
C14A—H180.9700C3Y—C2Y1.497 (3)
C14A—H190.9700C3Y—H13'0.9700
C8A—C9A1.378 (3)C3Y—H14'0.9700
C8A—C7A1.407 (3)C2Y—H11'0.9700
C9A—C10A1.404 (3)C2Y—H12'0.9700
C9A—H30.9300O2X—H1'0.96 (3)
C6X—O4X—H10'109.5 (16)C6A—C7A—C8A122.8 (2)
C3A—O2A—H9104 (2)N2A—C11A—C12A109.53 (18)
C12A—N3A—C13A112.03 (16)N2A—C11A—H10109.8
C12A—N3A—H14108.9 (16)C12A—C11A—H10109.8
C13A—N3A—H14106.5 (16)N2A—C11A—H11109.8
C12A—N3A—H15112.5 (15)C12A—C11A—H11109.8
C13A—N3A—H15107.2 (15)H10—C11A—H11108.2
H14—N3A—H15109 (2)N3A—C12A—C11A111.11 (17)
C3B—O2B—H28109.5N3A—C12A—H13109.4
C13B—N3B—C12B110.49 (17)C11A—C12A—H13109.4
C13B—N3B—H33112.2 (15)N3A—C12A—H12109.4
C12B—N3B—H33110.1 (15)C11A—C12A—H12109.4
C13B—N3B—H34110.6 (16)H13—C12A—H12108.0
C12B—N3B—H34107.2 (16)N3B—C13B—C14B109.31 (18)
H33—N3B—H34106 (2)N3B—C13B—H36109.8
C8A—N2A—C14A118.07 (17)C14B—C13B—H36109.8
C8A—N2A—C11A117.93 (17)N3B—C13B—H35109.8
C14A—N2A—C11A111.41 (16)C14B—C13B—H35109.8
C1A—N1A—C10A119.31 (19)H36—C13B—H35108.3
C1A—N1A—C15A119.40 (19)N2B—C14B—C13B110.39 (18)
C10A—N1A—C15A121.29 (18)N2B—C14B—H37109.6
C6A—C5A—C10A118.47 (19)C13B—C14B—H37109.6
C6A—C5A—C4A120.7 (2)N2B—C14B—H38109.6
C10A—C5A—C4A120.9 (2)C13B—C14B—H38109.6
C8B—N2B—C14B115.58 (17)H37—C14B—H38108.1
C8B—N2B—C11B112.37 (17)C9B—C8B—C7B117.02 (19)
C14B—N2B—C11B110.34 (16)C9B—C8B—N2B123.54 (19)
O2Y—C1Y—O1Y123.83 (18)C7B—C8B—N2B119.44 (19)
O2Y—C1Y—C2Y120.14 (18)F1B—C7B—C6B119.2 (2)
O1Y—C1Y—C2Y116.03 (17)F1B—C7B—C8B118.1 (2)
O1X—C1X—O2X123.6 (2)C6B—C7B—C8B122.7 (2)
O1X—C1X—C2X122.2 (2)C7B—C6B—C5B120.2 (2)
O2X—C1X—C2X114.16 (19)C7B—C6B—H21119.9
C1X—C2X—C3X116.91 (19)C5B—C6B—H21119.9
C1X—C2X—H3'108.1C10B—C5B—C6B118.4 (2)
C3X—C2X—H3'108.1C10B—C5B—C4B120.5 (2)
C1X—C2X—H2'108.1C6B—C5B—C4B121.0 (2)
C3X—C2X—H2'108.1O3B—C4B—C2B123.3 (2)
H3'—C2X—H2'107.3O3B—C4B—C5B120.4 (3)
C2X—C3X—C4X112.96 (18)C2B—C4B—C5B116.3 (2)
C2X—C3X—H5'109.0C1B—C2B—C4B120.0 (2)
C4X—C3X—H5'109.0C1B—C2B—C3B118.5 (3)
C2X—C3X—H4'109.0C4B—C2B—C3B121.5 (3)
C4X—C3X—H4'109.0O1B—C3B—O2B121.7 (3)
H5'—C3X—H4'107.8O1B—C3B—C2B123.6 (3)
C5X—C4X—C3X111.64 (18)O2B—C3B—C2B114.6 (3)
C5X—C4X—H7'109.3N2B—C11B—C12B110.97 (18)
C3X—C4X—H7'109.3N2B—C11B—H30109.4
C5X—C4X—H6'109.3C12B—C11B—H30109.4
C3X—C4X—H6'109.3N2B—C11B—H29109.4
H7'—C4X—H6'108.0C12B—C11B—H29109.4
C6X—C5X—C4X115.04 (18)H30—C11B—H29108.0
C6X—C5X—H9'108.5N3B—C12B—C11B109.94 (17)
C4X—C5X—H9'108.5N3B—C12B—H31109.7
C6X—C5X—H8'108.5C11B—C12B—H31109.7
C4X—C5X—H8'108.5N3B—C12B—H32109.7
H9'—C5X—H8'107.5C11B—C12B—H32109.7
O3X—C6X—O4X122.82 (19)H31—C12B—H32108.2
O3X—C6X—C5X124.5 (2)C8B—C9B—C10B121.4 (2)
O4X—C6X—C5X112.68 (19)C8B—C9B—H22119.3
N3A—C13A—C14A109.33 (17)C10B—C9B—H22119.3
N3A—C13A—H17109.8C5B—C10B—N1B119.3 (2)
C14A—C13A—H17109.8C5B—C10B—C9B120.1 (2)
N3A—C13A—H16109.8N1B—C10B—C9B120.6 (2)
C14A—C13A—H16109.8C1B—N1B—C10B119.4 (2)
H17—C13A—H16108.3C1B—N1B—C15B118.7 (2)
N2A—C14A—C13A107.46 (17)C10B—N1B—C15B121.6 (2)
N2A—C14A—H18110.2N1B—C1B—C2B124.4 (3)
C13A—C14A—H18110.2N1B—C1B—H20117.8
N2A—C14A—H19110.2C2B—C1B—H20117.8
C13A—C14A—H19110.2C16B—C15B—N1B112.2 (3)
H18—C14A—H19108.5C16B—C15B—H23116.3 (17)
C9A—C8A—N2A123.10 (19)N1B—C15B—H23112.9 (17)
C9A—C8A—C7A117.59 (19)C16B—C15B—H24117.6 (19)
N2A—C8A—C7A119.13 (19)N1B—C15B—H24105.4 (19)
C8A—C9A—C10A121.1 (2)H23—C15B—H2490 (2)
C8A—C9A—H3119.5C15B—C16B—H25109.5
C10A—C9A—H3119.5C15B—C16B—H27109.5
N1A—C10A—C9A120.71 (19)H25—C16B—H27109.5
N1A—C10A—C5A119.27 (18)C15B—C16B—H26109.5
C9A—C10A—C5A120.02 (19)H25—C16B—H26109.5
N1A—C1A—C2A124.4 (2)H27—C16B—H26109.5
N1A—C1A—H1117.8O4Y—C6Y—O3Y124.31 (18)
C2A—C1A—H1117.8O4Y—C6Y—C5Y119.05 (19)
C1A—C2A—C4A120.1 (2)O3Y—C6Y—C5Y116.63 (18)
C1A—C2A—C3A118.0 (2)C4Y—C5Y—C6Y116.81 (18)
C4A—C2A—C3A121.8 (2)C4Y—C5Y—H18'108.1
O1A—C3A—O2A121.3 (2)C6Y—C5Y—H18'108.1
O1A—C3A—C2A123.6 (2)C4Y—C5Y—H17'108.1
O2A—C3A—C2A115.1 (2)C6Y—C5Y—H17'108.1
N1A—C15A—C16A112.6 (2)H18'—C5Y—H17'107.3
N1A—C15A—H5109.1C5Y—C4Y—C3Y113.47 (19)
C16A—C15A—H5109.1C5Y—C4Y—H16'108.9
N1A—C15A—H4109.1C3Y—C4Y—H16'108.9
C16A—C15A—H4109.1C5Y—C4Y—H15'108.9
H5—C15A—H4107.8C3Y—C4Y—H15'108.9
C15A—C16A—H8109.5H16'—C4Y—H15'107.7
C15A—C16A—H7109.5C2Y—C3Y—C4Y113.76 (19)
H8—C16A—H7109.5C2Y—C3Y—H13'108.8
C15A—C16A—H6109.5C4Y—C3Y—H13'108.8
H8—C16A—H6109.5C2Y—C3Y—H14'108.8
H7—C16A—H6109.5C4Y—C3Y—H14'108.8
O3A—C4A—C2A122.9 (2)H13'—C3Y—H14'107.7
O3A—C4A—C5A121.3 (2)C3Y—C2Y—C1Y116.22 (17)
C2A—C4A—C5A115.8 (2)C3Y—C2Y—H11'108.2
C7A—C6A—C5A120.0 (2)C1Y—C2Y—H11'108.2
C7A—C6A—H2120.0C3Y—C2Y—H12'108.2
C5A—C6A—H2120.0C1Y—C2Y—H12'108.2
F1A—C7A—C6A119.8 (2)H11'—C2Y—H12'107.4
F1A—C7A—C8A117.36 (18)C1X—O2X—H1'112.4 (18)
O1X—C1X—C2X—C3X169.5 (2)C12B—N3B—C13B—C14B58.6 (2)
O2X—C1X—C2X—C3X9.5 (3)C8B—N2B—C14B—C13B172.39 (18)
C1X—C2X—C3X—C4X176.68 (19)C11B—N2B—C14B—C13B58.8 (2)
C2X—C3X—C4X—C5X175.54 (19)N3B—C13B—C14B—N2B59.3 (2)
C3X—C4X—C5X—C6X172.96 (19)C14B—N2B—C8B—C9B16.1 (3)
C4X—C5X—C6X—O3X5.3 (3)C11B—N2B—C8B—C9B111.7 (2)
C4X—C5X—C6X—O4X173.46 (18)C14B—N2B—C8B—C7B164.4 (2)
C12A—N3A—C13A—C14A56.5 (2)C11B—N2B—C8B—C7B67.7 (3)
C8A—N2A—C14A—C13A154.21 (18)C9B—C8B—C7B—F1B176.6 (2)
C11A—N2A—C14A—C13A64.6 (2)N2B—C8B—C7B—F1B3.9 (3)
N3A—C13A—C14A—N2A61.1 (2)C9B—C8B—C7B—C6B3.9 (3)
C14A—N2A—C8A—C9A24.0 (3)N2B—C8B—C7B—C6B175.6 (2)
C11A—N2A—C8A—C9A114.7 (2)F1B—C7B—C6B—C5B179.4 (2)
C14A—N2A—C8A—C7A151.1 (2)C8B—C7B—C6B—C5B1.1 (4)
C11A—N2A—C8A—C7A70.2 (3)C7B—C6B—C5B—C10B2.1 (3)
N2A—C8A—C9A—C10A173.2 (2)C7B—C6B—C5B—C4B175.6 (2)
C7A—C8A—C9A—C10A1.9 (3)C10B—C5B—C4B—O3B176.5 (2)
C1A—N1A—C10A—C9A176.8 (2)C6B—C5B—C4B—O3B1.1 (3)
C15A—N1A—C10A—C9A4.3 (3)C10B—C5B—C4B—C2B2.3 (3)
C1A—N1A—C10A—C5A4.2 (3)C6B—C5B—C4B—C2B179.9 (2)
C15A—N1A—C10A—C5A174.7 (2)O3B—C4B—C2B—C1B177.9 (2)
C8A—C9A—C10A—N1A179.3 (2)C5B—C4B—C2B—C1B0.9 (3)
C8A—C9A—C10A—C5A0.3 (3)O3B—C4B—C2B—C3B0.8 (4)
C6A—C5A—C10A—N1A177.7 (2)C5B—C4B—C2B—C3B179.5 (2)
C4A—C5A—C10A—N1A3.1 (3)C1B—C2B—C3B—O1B3.6 (4)
C6A—C5A—C10A—C9A1.4 (3)C4B—C2B—C3B—O1B177.8 (3)
C4A—C5A—C10A—C9A177.8 (2)C1B—C2B—C3B—O2B176.6 (2)
C10A—N1A—C1A—C2A1.5 (4)C4B—C2B—C3B—O2B2.0 (4)
C15A—N1A—C1A—C2A177.4 (2)C8B—N2B—C11B—C12B171.82 (18)
N1A—C1A—C2A—C4A2.2 (4)C14B—N2B—C11B—C12B57.6 (2)
N1A—C1A—C2A—C3A179.9 (2)C13B—N3B—C12B—C11B57.5 (2)
C1A—C2A—C3A—O1A2.3 (4)N2B—C11B—C12B—N3B56.6 (2)
C4A—C2A—C3A—O1A180.0 (2)C7B—C8B—C9B—C10B3.4 (3)
C1A—C2A—C3A—O2A176.7 (2)N2B—C8B—C9B—C10B176.0 (2)
C4A—C2A—C3A—O2A0.9 (3)C6B—C5B—C10B—N1B179.3 (2)
C1A—N1A—C15A—C16A97.2 (3)C4B—C5B—C10B—N1B3.0 (3)
C10A—N1A—C15A—C16A83.9 (3)C6B—C5B—C10B—C9B2.5 (3)
C1A—C2A—C4A—O3A177.0 (2)C4B—C5B—C10B—C9B175.2 (2)
C3A—C2A—C4A—O3A0.6 (3)C8B—C9B—C10B—C5B0.3 (3)
C1A—C2A—C4A—C5A3.1 (3)C8B—C9B—C10B—N1B177.8 (2)
C3A—C2A—C4A—C5A179.3 (2)C5B—C10B—N1B—C1B2.3 (3)
C6A—C5A—C4A—O3A1.2 (3)C9B—C10B—N1B—C1B175.9 (2)
C10A—C5A—C4A—O3A179.6 (2)C5B—C10B—N1B—C15B176.3 (3)
C6A—C5A—C4A—C2A178.7 (2)C9B—C10B—N1B—C15B1.8 (4)
C10A—C5A—C4A—C2A0.5 (3)C10B—N1B—C1B—C2B1.0 (4)
C10A—C5A—C6A—C7A1.3 (3)C15B—N1B—C1B—C2B175.2 (3)
C4A—C5A—C6A—C7A177.9 (2)C4B—C2B—C1B—N1B0.3 (4)
C5A—C6A—C7A—F1A177.1 (2)C3B—C2B—C1B—N1B178.9 (2)
C5A—C6A—C7A—C8A0.4 (4)C1B—N1B—C15B—C16B92.1 (3)
C9A—C8A—C7A—F1A178.8 (2)C10B—N1B—C15B—C16B82.0 (3)
N2A—C8A—C7A—F1A3.5 (3)O4Y—C6Y—C5Y—C4Y6.8 (3)
C9A—C8A—C7A—C6A2.0 (3)O3Y—C6Y—C5Y—C4Y174.2 (2)
N2A—C8A—C7A—C6A173.3 (2)C6Y—C5Y—C4Y—C3Y170.3 (2)
C8A—N2A—C11A—C12A158.14 (19)C5Y—C4Y—C3Y—C2Y58.2 (3)
C14A—N2A—C11A—C12A60.6 (2)C4Y—C3Y—C2Y—C1Y171.8 (2)
C13A—N3A—C12A—C11A52.4 (2)O2Y—C1Y—C2Y—C3Y5.6 (3)
N2A—C11A—C12A—N3A53.0 (2)O1Y—C1Y—C2Y—C3Y174.5 (2)
(20120156_0m) top
Crystal data top
C41H57F2N6O21V = 2204.38 (13) Å3
Mr = 1007.93Z = 2
Triclinic, P1F(000) = 1062
a = 7.4031 (3) ÅDx = 1.518 Mg m3
b = 9.7515 (3) ÅMo Kα radiation, λ = 0.71073 Å
c = 30.9801 (10) ŵ = 0.13 mm1
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 top
CCD area detector
diffractometer
4274 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.059
Graphite monochromatorθmax = 25.0°, θmin = 1.3°
phi and ω scansh = 88
31596 measured reflectionsk = 1111
7784 independent reflectionsl = 3636
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.056P)2 + 0.3322P]
where P = (Fo2 + 2Fc2)/3
7784 reflections(Δ/σ)max = 0.001
673 parametersΔρmax = 0.41 e Å3
14 restraintsΔρmin = 0.31 e Å3
Crystal data top
C41H57F2N6O21γ = 81.380 (2)°
Mr = 1007.93V = 2204.38 (13) Å3
Triclinic, P1Z = 2
a = 7.4031 (3) ÅMo Kα radiation
b = 9.7515 (3) ŵ = 0.13 mm1
c = 30.9801 (10) ÅT = 100 K
α = 88.088 (2)°0.21 × 0.08 × 0.05 mm
β = 85.673 (2)°
Data collection top
CCD area detector
diffractometer
4274 reflections with I > 2σ(I)
31596 measured reflectionsRint = 0.059
7784 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05214 restraints
wR(F2) = 0.131H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.41 e Å3
7784 reflectionsΔρmin = 0.31 e Å3
673 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
H2B0.333 (7)0.926 (5)0.9142 (16)0.122 (19)*
H2A0.325 (5)0.835 (4)0.9506 (12)0.072 (15)*
O2S0.3966 (3)0.8792 (3)0.93735 (9)0.0513 (7)
O1Y0.8893 (3)0.2461 (2)1.02422 (7)0.0405 (6)
O3Y0.7950 (3)0.5381 (2)0.95190 (7)0.0511 (7)
H1'0.86110.48880.93430.077*
O4Y0.5320 (3)0.3592 (2)0.96084 (7)0.0419 (6)
H4Y0.42600.34330.96350.063*
O2Y1.0077 (3)0.3019 (2)0.95873 (7)0.0414 (6)
C1Y0.8976 (4)0.3251 (3)0.99085 (10)0.0293 (8)
C2Y0.7658 (4)0.4600 (3)0.99086 (10)0.0319 (8)
H2'0.79060.51471.01510.038*
C3Y0.5681 (4)0.4335 (3)0.99746 (9)0.0293 (8)
H3'0.55520.37501.02350.035*
O3X0.5823 (3)0.1571 (2)0.43764 (7)0.0369 (6)
H6'0.65540.21160.43180.055*
O4X0.6539 (2)0.0815 (2)0.52956 (6)0.0296 (5)
H8'0.76560.07020.53030.044*
O1S0.3279 (4)0.1470 (3)0.97959 (8)0.0450 (7)
O2A1.2065 (4)0.1025 (3)0.88170 (8)0.0639 (8)
H11.16270.18470.88020.096*
O1A1.2958 (4)0.0690 (3)0.83684 (9)0.0705 (9)
F1A0.7822 (3)0.7158 (2)0.75906 (6)0.0520 (5)
O2B0.3489 (3)0.6531 (3)0.67071 (8)0.0521 (7)
O1B0.2921 (5)0.8080 (3)0.72134 (9)0.0818 (10)
F1B0.8147 (3)0.00155 (19)0.77003 (5)0.0505 (5)
O1X0.9884 (3)0.0765 (2)0.45757 (6)0.0313 (5)
O2X0.9322 (3)0.1462 (2)0.43767 (7)0.0418 (6)
O1Z0.1139 (3)0.3142 (3)0.52312 (7)0.0418 (6)
O4Z0.5887 (3)0.3643 (2)0.53742 (7)0.0400 (6)
H12'0.615 (5)0.281 (4)0.5310 (11)0.060*
N2A0.8575 (3)0.6311 (3)0.67358 (7)0.0329 (7)
N1A1.1772 (4)0.1980 (3)0.73092 (8)0.0372 (6)
O3A1.0445 (3)0.3286 (3)0.85514 (7)0.0565 (7)
N2B0.7639 (3)0.0598 (2)0.85922 (7)0.0281 (6)
N3B0.8142 (3)0.1320 (3)0.93231 (7)0.0352 (7)
H340.69790.14170.94100.042*
H330.88880.18530.94980.042*
O3B0.5025 (3)0.4101 (2)0.68871 (7)0.0444 (6)
O2Z0.1984 (3)0.3199 (3)0.59078 (8)0.0585 (7)
N3A0.7474 (4)0.7978 (3)0.59967 (9)0.0398 (8)
C12A0.7312 (4)0.8547 (3)0.64372 (11)0.0443 (9)
H130.61140.84580.65750.053*
H120.74270.95250.64180.053*
C11A0.8768 (5)0.7794 (3)0.67058 (10)0.0404 (9)
H100.99690.79040.65740.048*
H110.86450.81770.69930.048*
C8A0.9284 (4)0.5491 (3)0.70795 (9)0.0285 (8)
C9A1.0300 (4)0.4190 (3)0.70216 (9)0.0297 (8)
H81.06500.38900.67420.036*
C10A1.0815 (4)0.3314 (3)0.73714 (9)0.0278 (7)
C1A1.2175 (4)0.1148 (4)0.76530 (11)0.0414 (9)
H21.27710.02530.76020.050*
C2A1.1764 (4)0.1531 (4)0.80742 (10)0.0382 (9)
C3A1.2312 (5)0.0514 (5)0.84246 (12)0.0494 (10)
C15A1.2331 (5)0.1443 (4)0.68672 (10)0.0452 (7)
H41.27320.21790.66830.054*
H31.33540.06990.68820.054*
C16A1.0805 (5)0.0924 (4)0.66773 (11)0.0605 (10)
H51.03450.02460.68700.091*
H61.12300.05070.64050.091*
H70.98430.16820.66330.091*
C5A1.0367 (4)0.3767 (3)0.77983 (9)0.0320 (8)
C4A1.0853 (4)0.2871 (4)0.81688 (11)0.0383 (9)
C6A0.9397 (4)0.5104 (4)0.78577 (10)0.0368 (8)
H90.91130.54370.81360.044*
C7A0.8873 (4)0.5912 (3)0.75141 (10)0.0351 (8)
C13A0.7483 (4)0.6455 (3)0.60107 (10)0.0406 (9)
H160.77610.61020.57210.049*
H170.62710.62600.61100.049*
C14A0.8859 (4)0.5715 (3)0.63048 (9)0.0359 (8)
H190.87370.47380.63260.043*
H181.00880.57940.61840.043*
C3B0.3466 (5)0.6907 (4)0.71129 (12)0.0463 (9)
C2B0.4164 (4)0.5785 (3)0.74194 (10)0.0347 (8)
C4B0.4923 (4)0.4445 (3)0.72801 (10)0.0327 (8)
C5B0.5596 (4)0.3467 (3)0.76188 (9)0.0294 (8)
C6B0.6495 (4)0.2134 (3)0.75146 (9)0.0322 (8)
H210.66380.18640.72280.039*
C7B0.7154 (4)0.1241 (3)0.78281 (10)0.0312 (8)
C8B0.6919 (4)0.1536 (3)0.82764 (9)0.0277 (7)
C11B0.7384 (5)0.0864 (3)0.85643 (10)0.0377 (8)
H300.77050.11710.82700.045*
H290.61050.09480.86350.045*
C12B0.8556 (4)0.1783 (3)0.88711 (9)0.0377 (8)
H310.83320.27330.88520.045*
H320.98390.17560.87870.045*
C1B0.4101 (4)0.6100 (4)0.78500 (11)0.0425 (9)
H280.36110.69960.79310.051*
N1B0.4705 (4)0.5194 (3)0.81605 (8)0.0392 (7)
C10B0.5440 (4)0.3837 (3)0.80550 (10)0.0308 (8)
C13B0.8394 (5)0.0145 (3)0.93556 (10)0.0373 (8)
H360.96810.02220.92980.045*
H350.80300.04490.96480.045*
C14B0.7290 (4)0.1084 (3)0.90421 (9)0.0334 (8)
H370.59970.11240.91290.040*
H380.75950.20140.90540.040*
C9B0.6035 (4)0.2858 (3)0.83745 (9)0.0322 (8)
H220.58300.31030.86630.039*
C15B0.4569 (5)0.5708 (4)0.86199 (10)0.0503 (10)
H230.55710.52180.87750.060*
H240.46660.66890.86150.060*
C16B0.2815 (6)0.5480 (5)0.88439 (13)0.0742 (13)
H250.18300.58700.86720.111*
H260.26720.59190.91200.111*
H270.27970.45030.88860.111*
C1X0.8834 (4)0.0320 (3)0.44884 (9)0.0250 (7)
C2X0.6776 (4)0.0282 (3)0.45211 (9)0.0243 (7)
H5'0.65380.04400.43290.029*
C3X0.6045 (3)0.0070 (3)0.49800 (9)0.0216 (7)
H7'0.65480.10310.50520.026*
C1Z0.1923 (4)0.3659 (3)0.55439 (11)0.0333 (8)
C2Z0.2832 (4)0.4898 (3)0.53881 (9)0.0315 (8)
H11'0.19930.55240.52150.038*
C3Z0.4582 (4)0.4394 (3)0.51077 (9)0.0282 (7)
H13'0.43010.37850.48840.034*
H150.863 (6)0.817 (4)0.5863 (12)0.082 (13)*
H140.649 (5)0.830 (4)0.5860 (10)0.056 (11)*
O3S0.6622 (7)0.2085 (5)0.62770 (12)0.173 (2)
H3A0.64930.24930.60320.259*
H3B0.64260.27010.64690.259*
H1B0.214 (6)0.193 (4)0.9707 (12)0.083 (15)*
H1A0.356 (7)0.068 (5)0.9669 (16)0.12 (2)*
H9'0.074 (5)0.233 (4)0.5329 (12)0.081 (14)*
H200.396 (5)0.556 (4)0.6688 (11)0.063 (13)*
O3Z0.3255 (3)0.5618 (2)0.57498 (7)0.0463 (6)
H10'0.36190.50560.59390.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2S0.0418 (16)0.0528 (19)0.0588 (18)0.0096 (14)0.0060 (14)0.0240 (14)
O1Y0.0354 (13)0.0401 (15)0.0438 (13)0.0014 (11)0.0050 (11)0.0163 (11)
O3Y0.0431 (16)0.0450 (16)0.0607 (16)0.0021 (12)0.0045 (12)0.0258 (13)
O4Y0.0313 (13)0.0465 (15)0.0482 (14)0.0055 (11)0.0002 (11)0.0144 (12)
O2Y0.0351 (13)0.0449 (16)0.0403 (14)0.0028 (12)0.0058 (11)0.0009 (11)
C1Y0.0214 (17)0.031 (2)0.0367 (19)0.0055 (15)0.0066 (15)0.0000 (16)
C2Y0.0292 (18)0.029 (2)0.0360 (18)0.0017 (16)0.0022 (14)0.0064 (15)
C3Y0.0327 (19)0.0235 (19)0.0315 (18)0.0037 (14)0.0030 (15)0.0007 (15)
O3X0.0238 (12)0.0345 (14)0.0526 (14)0.0077 (11)0.0063 (10)0.0209 (11)
O4X0.0149 (10)0.0367 (14)0.0381 (12)0.0044 (10)0.0035 (9)0.0057 (10)
O1S0.0390 (16)0.0474 (19)0.0480 (15)0.0050 (14)0.0016 (12)0.0021 (14)
O2A0.0687 (19)0.082 (2)0.0447 (16)0.0219 (18)0.0208 (14)0.0332 (15)
O1A0.0666 (19)0.061 (2)0.079 (2)0.0027 (17)0.0167 (15)0.0390 (17)
F1A0.0683 (14)0.0350 (13)0.0487 (12)0.0026 (11)0.0036 (10)0.0058 (10)
O2B0.0572 (17)0.057 (2)0.0402 (16)0.0042 (15)0.0074 (12)0.0151 (14)
O1B0.134 (3)0.0415 (19)0.0628 (18)0.016 (2)0.0245 (18)0.0125 (15)
F1B0.0719 (14)0.0332 (12)0.0395 (11)0.0107 (11)0.0047 (10)0.0030 (9)
O1X0.0176 (11)0.0286 (14)0.0481 (13)0.0039 (10)0.0036 (10)0.0002 (10)
O2X0.0257 (12)0.0384 (15)0.0611 (15)0.0100 (11)0.0009 (11)0.0164 (12)
O1Z0.0406 (14)0.0365 (16)0.0521 (15)0.0174 (12)0.0054 (12)0.0011 (13)
O4Z0.0405 (14)0.0300 (14)0.0478 (14)0.0011 (13)0.0080 (11)0.0047 (12)
N2A0.0431 (17)0.0264 (16)0.0299 (15)0.0069 (13)0.0065 (12)0.0055 (12)
N1A0.0484 (15)0.0273 (15)0.0342 (12)0.0005 (12)0.0061 (12)0.0091 (11)
O3A0.0779 (19)0.0683 (19)0.0277 (14)0.0241 (15)0.0102 (13)0.0071 (13)
N2B0.0344 (15)0.0212 (15)0.0280 (14)0.0016 (12)0.0028 (11)0.0011 (12)
N3B0.0365 (16)0.0327 (17)0.0340 (15)0.0002 (13)0.0011 (12)0.0102 (13)
O3B0.0554 (15)0.0491 (16)0.0286 (13)0.0068 (13)0.0059 (11)0.0035 (11)
O2Z0.0802 (19)0.0579 (18)0.0410 (15)0.0280 (15)0.0037 (13)0.0092 (13)
N3A0.0218 (17)0.050 (2)0.0473 (19)0.0057 (15)0.0082 (15)0.0218 (16)
C12A0.041 (2)0.031 (2)0.059 (2)0.0034 (18)0.0023 (18)0.0119 (18)
C11A0.050 (2)0.029 (2)0.045 (2)0.0125 (17)0.0101 (17)0.0113 (16)
C8A0.0289 (18)0.027 (2)0.0304 (18)0.0065 (16)0.0044 (14)0.0055 (15)
C9A0.0334 (19)0.031 (2)0.0253 (17)0.0057 (16)0.0019 (14)0.0009 (15)
C10A0.0284 (18)0.027 (2)0.0289 (18)0.0079 (15)0.0036 (14)0.0059 (15)
C1A0.040 (2)0.031 (2)0.052 (2)0.0050 (17)0.0069 (17)0.0127 (18)
C2A0.036 (2)0.044 (2)0.037 (2)0.0127 (18)0.0126 (16)0.0196 (18)
C3A0.039 (2)0.065 (3)0.048 (3)0.020 (2)0.0120 (19)0.025 (2)
C15A0.0591 (17)0.0336 (16)0.0395 (13)0.0024 (14)0.0024 (13)0.0058 (12)
C16A0.081 (2)0.050 (2)0.054 (2)0.0178 (19)0.0044 (18)0.0011 (18)
C5A0.0346 (19)0.033 (2)0.0311 (18)0.0142 (17)0.0066 (15)0.0079 (16)
C4A0.038 (2)0.046 (3)0.036 (2)0.0214 (19)0.0077 (16)0.0101 (18)
C6A0.045 (2)0.040 (2)0.0272 (18)0.0152 (19)0.0007 (15)0.0000 (16)
C7A0.038 (2)0.025 (2)0.042 (2)0.0037 (17)0.0002 (16)0.0027 (16)
C13A0.039 (2)0.045 (2)0.040 (2)0.0134 (18)0.0094 (16)0.0128 (17)
C14A0.041 (2)0.035 (2)0.0322 (18)0.0053 (17)0.0046 (15)0.0050 (16)
C3B0.050 (2)0.046 (3)0.042 (2)0.005 (2)0.0054 (18)0.011 (2)
C2B0.0317 (19)0.034 (2)0.036 (2)0.0007 (17)0.0010 (15)0.0081 (16)
C4B0.0251 (18)0.037 (2)0.036 (2)0.0083 (16)0.0015 (15)0.0070 (17)
C5B0.0279 (18)0.027 (2)0.0327 (18)0.0058 (16)0.0004 (14)0.0056 (15)
C6B0.0362 (19)0.035 (2)0.0256 (17)0.0068 (17)0.0002 (14)0.0019 (15)
C7B0.0352 (19)0.0218 (19)0.0341 (19)0.0017 (16)0.0021 (15)0.0008 (15)
C8B0.0233 (17)0.030 (2)0.0294 (18)0.0026 (15)0.0013 (14)0.0028 (15)
C11B0.049 (2)0.026 (2)0.0390 (19)0.0048 (17)0.0072 (16)0.0030 (15)
C12B0.043 (2)0.028 (2)0.039 (2)0.0029 (17)0.0009 (16)0.0017 (16)
C1B0.048 (2)0.030 (2)0.045 (2)0.0064 (17)0.0015 (17)0.0078 (17)
N1B0.0539 (19)0.0276 (18)0.0310 (15)0.0091 (15)0.0008 (13)0.0026 (13)
C10B0.0323 (19)0.026 (2)0.0336 (19)0.0023 (16)0.0004 (15)0.0001 (15)
C13B0.050 (2)0.031 (2)0.0326 (18)0.0079 (17)0.0081 (16)0.0071 (15)
C14B0.041 (2)0.029 (2)0.0280 (18)0.0021 (16)0.0002 (15)0.0017 (15)
C9B0.0348 (19)0.033 (2)0.0269 (17)0.0005 (17)0.0003 (14)0.0019 (15)
C15B0.074 (3)0.026 (2)0.042 (2)0.015 (2)0.005 (2)0.0007 (17)
C16B0.074 (3)0.083 (4)0.064 (3)0.001 (3)0.010 (2)0.016 (2)
C1X0.0236 (17)0.027 (2)0.0238 (16)0.0045 (16)0.0009 (13)0.0006 (14)
C2X0.0195 (16)0.0233 (18)0.0297 (17)0.0036 (14)0.0001 (13)0.0043 (14)
C3X0.0165 (15)0.0183 (17)0.0298 (16)0.0021 (14)0.0024 (13)0.0001 (13)
C1Z0.0289 (19)0.030 (2)0.041 (2)0.0069 (16)0.0048 (16)0.0066 (17)
C2Z0.0334 (19)0.027 (2)0.0349 (18)0.0074 (16)0.0022 (15)0.0046 (15)
C3Z0.0318 (19)0.0219 (18)0.0315 (17)0.0054 (15)0.0021 (14)0.0021 (14)
O3S0.231 (5)0.155 (4)0.104 (3)0.062 (4)0.016 (3)0.007 (3)
O3Z0.0557 (16)0.0410 (15)0.0445 (14)0.0179 (14)0.0095 (12)0.0162 (12)
Geometric parameters (Å, º) top
O2S—H2B0.95 (5)C1A—H20.9300
O2S—H2A0.81 (4)C2A—C4A1.407 (5)
O1Y—C1Y1.272 (3)C2A—C3A1.483 (5)
O3Y—C2Y1.425 (3)C15A—C16A1.473 (4)
O3Y—H1'0.8200C15A—H40.9700
O4Y—C3Y1.429 (3)C15A—H30.9700
O4Y—H4Y0.8200C16A—H50.9600
O2Y—C1Y1.242 (3)C16A—H60.9600
C1Y—C2Y1.516 (4)C16A—H70.9600
C2Y—C3Y1.522 (4)C5A—C6A1.402 (4)
C2Y—H2'0.9800C5A—C4A1.453 (4)
C3Y—C3Yi1.523 (6)C6A—C7A1.348 (4)
C3Y—H3'0.9800C6A—H90.9300
O3X—C2X1.422 (3)C13A—C14A1.505 (4)
O3X—H6'0.8200C13A—H160.9700
O4X—C3X1.428 (3)C13A—H170.9700
O4X—H8'0.8200C14A—H190.9700
O1S—H1B0.95 (4)C14A—H180.9700
O1S—H1A0.87 (5)C3B—C2B1.483 (5)
O2A—C3A1.318 (4)C2B—C1B1.375 (4)
O2A—H10.8200C2B—C4B1.411 (4)
O1A—C3A1.213 (4)C4B—C5B1.459 (4)
F1A—C7A1.359 (3)C5B—C10B1.402 (4)
O2B—C3B1.320 (4)C5B—C6B1.405 (4)
O2B—H200.96 (4)C6B—C7B1.352 (4)
O1B—C3B1.198 (4)C6B—H210.9300
F1B—C7B1.360 (3)C7B—C8B1.420 (4)
O1X—C1X1.251 (3)C8B—C9B1.388 (4)
O2X—C1X1.251 (3)C11B—C12B1.514 (4)
O1Z—C1Z1.317 (4)C11B—H300.9700
O1Z—H9'0.92 (4)C11B—H290.9700
O4Z—C3Z1.422 (3)C12B—H310.9700
O4Z—H12'0.83 (4)C12B—H320.9700
N2A—C8A1.397 (3)C1B—N1B1.340 (4)
N2A—C14A1.462 (4)C1B—H280.9300
N2A—C11A1.473 (4)N1B—C10B1.393 (4)
N1A—C1A1.342 (4)N1B—C15B1.516 (4)
N1A—C10A1.397 (4)C10B—C9B1.401 (4)
N1A—C15A1.489 (4)C13B—C14B1.511 (4)
O3A—C4A1.266 (4)C13B—H360.9700
N2B—C8B1.397 (4)C13B—H350.9700
N2B—C11B1.472 (4)C14B—H370.9700
N2B—C14B1.479 (4)C14B—H380.9700
N3B—C13B1.477 (4)C9B—H220.9300
N3B—C12B1.481 (4)C15B—C16B1.468 (5)
N3B—H340.9000C15B—H230.9700
N3B—H330.9000C15B—H240.9700
O3B—C4B1.268 (3)C16B—H250.9600
O2Z—C1Z1.201 (4)C16B—H260.9600
N3A—C12A1.480 (4)C16B—H270.9600
N3A—C13A1.483 (4)C1X—C2X1.525 (4)
N3A—H150.97 (4)C2X—C3X1.529 (4)
N3A—H140.88 (3)C2X—H5'0.9800
C12A—C11A1.500 (4)C3X—C3Xii1.528 (5)
C12A—H130.9700C3X—H7'0.9800
C12A—H120.9700C1Z—C2Z1.517 (4)
C11A—H100.9700C2Z—O3Z1.420 (3)
C11A—H110.9700C2Z—C3Z1.530 (4)
C8A—C9A1.385 (4)C2Z—H11'0.9800
C8A—C7A1.418 (4)C3Z—C3Ziii1.526 (5)
C9A—C10A1.397 (4)C3Z—H13'0.9800
C9A—H80.9300O3S—H3A0.8500
C10A—C5A1.408 (4)O3S—H3B0.8498
C1A—C2A1.369 (4)O3Z—H10'0.8200
H2B—O2S—H2A106 (4)N2A—C14A—H19109.6
C2Y—O3Y—H1'109.5C13A—C14A—H19109.6
C3Y—O4Y—H4Y109.5N2A—C14A—H18109.6
O2Y—C1Y—O1Y125.2 (3)C13A—C14A—H18109.6
O2Y—C1Y—C2Y117.5 (3)H19—C14A—H18108.1
O1Y—C1Y—C2Y117.3 (3)O1B—C3B—O2B120.6 (3)
O3Y—C2Y—C1Y110.5 (2)O1B—C3B—C2B124.3 (4)
O3Y—C2Y—C3Y111.2 (2)O2B—C3B—C2B115.0 (4)
C1Y—C2Y—C3Y111.1 (2)C1B—C2B—C4B120.1 (3)
O3Y—C2Y—H2'108.0C1B—C2B—C3B117.7 (3)
C1Y—C2Y—H2'108.0C4B—C2B—C3B122.2 (3)
C3Y—C2Y—H2'108.0O3B—C4B—C2B122.8 (3)
O4Y—C3Y—C2Y107.2 (2)O3B—C4B—C5B121.6 (3)
O4Y—C3Y—C3Yi110.5 (3)C2B—C4B—C5B115.7 (3)
C2Y—C3Y—C3Yi112.9 (3)C10B—C5B—C6B117.7 (3)
O4Y—C3Y—H3'108.7C10B—C5B—C4B121.6 (3)
C2Y—C3Y—H3'108.7C6B—C5B—C4B120.7 (3)
C3Yi—C3Y—H3'108.7C7B—C6B—C5B120.6 (3)
C2X—O3X—H6'109.5C7B—C6B—H21119.7
C3X—O4X—H8'109.5C5B—C6B—H21119.7
H1B—O1S—H1A109 (4)C6B—C7B—F1B117.3 (3)
C3A—O2A—H1109.5C6B—C7B—C8B123.7 (3)
C3B—O2B—H20109 (2)F1B—C7B—C8B119.0 (3)
C1Z—O1Z—H9'109 (2)C9B—C8B—N2B122.5 (3)
C3Z—O4Z—H12'113 (3)C9B—C8B—C7B115.1 (3)
C8A—N2A—C14A117.4 (3)N2B—C8B—C7B122.3 (3)
C8A—N2A—C11A119.8 (2)N2B—C11B—C12B111.3 (3)
C14A—N2A—C11A109.9 (2)N2B—C11B—H30109.4
C1A—N1A—C10A119.7 (3)C12B—C11B—H30109.4
C1A—N1A—C15A118.8 (3)N2B—C11B—H29109.4
C10A—N1A—C15A121.5 (2)C12B—C11B—H29109.4
C8B—N2B—C11B118.1 (2)H30—C11B—H29108.0
C8B—N2B—C14B115.1 (2)N3B—C12B—C11B111.0 (3)
C11B—N2B—C14B111.3 (2)N3B—C12B—H31109.4
C13B—N3B—C12B110.3 (2)C11B—C12B—H31109.4
C13B—N3B—H34109.6N3B—C12B—H32109.4
C12B—N3B—H34109.6C11B—C12B—H32109.4
C13B—N3B—H33109.6H31—C12B—H32108.0
C12B—N3B—H33109.6N1B—C1B—C2B124.0 (3)
H34—N3B—H33108.1N1B—C1B—H28118.0
C12A—N3A—C13A111.5 (2)C2B—C1B—H28118.0
C12A—N3A—H15106 (2)C1B—N1B—C10B120.0 (3)
C13A—N3A—H15109 (2)C1B—N1B—C15B117.7 (3)
C12A—N3A—H14110 (2)C10B—N1B—C15B122.3 (2)
C13A—N3A—H14104 (2)N1B—C10B—C9B121.2 (3)
H15—N3A—H14116 (3)N1B—C10B—C5B118.6 (3)
N3A—C12A—C11A110.7 (3)C9B—C10B—C5B120.2 (3)
N3A—C12A—H13109.5N3B—C13B—C14B112.2 (2)
C11A—C12A—H13109.5N3B—C13B—H36109.2
N3A—C12A—H12109.5C14B—C13B—H36109.2
C11A—C12A—H12109.5N3B—C13B—H35109.2
H13—C12A—H12108.1C14B—C13B—H35109.2
N2A—C11A—C12A109.1 (3)H36—C13B—H35107.9
N2A—C11A—H10109.9N2B—C14B—C13B112.1 (3)
C12A—C11A—H10109.9N2B—C14B—H37109.2
N2A—C11A—H11109.9C13B—C14B—H37109.2
C12A—C11A—H11109.9N2B—C14B—H38109.2
H10—C11A—H11108.3C13B—C14B—H38109.2
C9A—C8A—N2A122.6 (3)H37—C14B—H38107.9
C9A—C8A—C7A116.2 (3)C8B—C9B—C10B122.6 (3)
N2A—C8A—C7A121.1 (3)C8B—C9B—H22118.7
C8A—C9A—C10A121.9 (3)C10B—C9B—H22118.7
C8A—C9A—H8119.0C16B—C15B—N1B110.2 (3)
C10A—C9A—H8119.0C16B—C15B—H23109.6
N1A—C10A—C9A121.4 (3)N1B—C15B—H23109.6
N1A—C10A—C5A118.5 (3)C16B—C15B—H24109.6
C9A—C10A—C5A120.1 (3)N1B—C15B—H24109.6
N1A—C1A—C2A124.2 (3)H23—C15B—H24108.1
N1A—C1A—H2117.9C15B—C16B—H25109.5
C2A—C1A—H2117.9C15B—C16B—H26109.5
C1A—C2A—C4A120.1 (3)H25—C16B—H26109.5
C1A—C2A—C3A118.8 (4)C15B—C16B—H27109.5
C4A—C2A—C3A121.1 (3)H25—C16B—H27109.5
O1A—C3A—O2A120.9 (3)H26—C16B—H27109.5
O1A—C3A—C2A124.7 (4)O1X—C1X—O2X125.5 (3)
O2A—C3A—C2A114.5 (4)O1X—C1X—C2X118.5 (3)
C16A—C15A—N1A111.2 (3)O2X—C1X—C2X116.0 (3)
C16A—C15A—H4109.4O3X—C2X—C1X110.2 (2)
N1A—C15A—H4109.4O3X—C2X—C3X110.0 (2)
C16A—C15A—H3109.4C1X—C2X—C3X112.5 (2)
N1A—C15A—H3109.4O3X—C2X—H5'108.0
H4—C15A—H3108.0C1X—C2X—H5'108.0
C15A—C16A—H5109.5C3X—C2X—H5'108.0
C15A—C16A—H6109.5O4X—C3X—C3Xii106.6 (3)
H5—C16A—H6109.5O4X—C3X—C2X112.5 (2)
C15A—C16A—H7109.5C3Xii—C3X—C2X111.8 (3)
H5—C16A—H7109.5O4X—C3X—H7'108.6
H6—C16A—H7109.5C3Xii—C3X—H7'108.6
C6A—C5A—C10A118.1 (3)C2X—C3X—H7'108.6
C6A—C5A—C4A120.5 (3)O2Z—C1Z—O1Z125.3 (3)
C10A—C5A—C4A121.4 (3)O2Z—C1Z—C2Z122.7 (3)
O3A—C4A—C2A123.0 (3)O1Z—C1Z—C2Z112.0 (3)
O3A—C4A—C5A121.0 (3)O3Z—C2Z—C1Z109.7 (2)
C2A—C4A—C5A116.0 (3)O3Z—C2Z—C3Z110.2 (2)
C7A—C6A—C5A120.5 (3)C1Z—C2Z—C3Z109.2 (2)
C7A—C6A—H9119.8O3Z—C2Z—H11'109.3
C5A—C6A—H9119.8C1Z—C2Z—H11'109.3
C6A—C7A—F1A118.1 (3)C3Z—C2Z—H11'109.3
C6A—C7A—C8A123.2 (3)O4Z—C3Z—C3Ziii108.2 (3)
F1A—C7A—C8A118.7 (3)O4Z—C3Z—C2Z108.9 (2)
N3A—C13A—C14A112.3 (3)C3Ziii—C3Z—C2Z111.5 (3)
N3A—C13A—H16109.1O4Z—C3Z—H13'109.4
C14A—C13A—H16109.1C3Ziii—C3Z—H13'109.4
N3A—C13A—H17109.1C2Z—C3Z—H13'109.4
C14A—C13A—H17109.1H3A—O3S—H3B107.7
H16—C13A—H17107.9C2Z—O3Z—H10'109.5
N2A—C14A—C13A110.4 (3)
O2Y—C1Y—C2Y—O3Y0.2 (4)C1B—C2B—C4B—O3B179.6 (3)
O1Y—C1Y—C2Y—O3Y178.6 (2)C3B—C2B—C4B—O3B1.6 (5)
O2Y—C1Y—C2Y—C3Y124.1 (3)C1B—C2B—C4B—C5B0.4 (4)
O1Y—C1Y—C2Y—C3Y57.5 (3)C3B—C2B—C4B—C5B178.3 (3)
O3Y—C2Y—C3Y—O4Y59.2 (3)O3B—C4B—C5B—C10B178.3 (3)
C1Y—C2Y—C3Y—O4Y64.3 (3)C2B—C4B—C5B—C10B1.7 (4)
O3Y—C2Y—C3Y—C3Yi62.7 (4)O3B—C4B—C5B—C6B4.4 (4)
C1Y—C2Y—C3Y—C3Yi173.8 (3)C2B—C4B—C5B—C6B175.5 (3)
C13A—N3A—C12A—C11A53.8 (4)C10B—C5B—C6B—C7B1.1 (4)
C8A—N2A—C11A—C12A157.1 (3)C4B—C5B—C6B—C7B178.5 (3)
C14A—N2A—C11A—C12A62.6 (3)C5B—C6B—C7B—F1B174.4 (3)
N3A—C12A—C11A—N2A59.5 (3)C5B—C6B—C7B—C8B3.3 (5)
C14A—N2A—C8A—C9A3.2 (4)C11B—N2B—C8B—C9B138.5 (3)
C11A—N2A—C8A—C9A134.3 (3)C14B—N2B—C8B—C9B3.7 (4)
C14A—N2A—C8A—C7A171.8 (3)C11B—N2B—C8B—C7B46.2 (4)
C11A—N2A—C8A—C7A50.7 (4)C14B—N2B—C8B—C7B179.0 (3)
N2A—C8A—C9A—C10A172.2 (3)C6B—C7B—C8B—C9B3.4 (4)
C7A—C8A—C9A—C10A3.0 (4)F1B—C7B—C8B—C9B174.3 (3)
C1A—N1A—C10A—C9A177.2 (3)C6B—C7B—C8B—N2B179.1 (3)
C15A—N1A—C10A—C9A1.6 (4)F1B—C7B—C8B—N2B1.4 (4)
C1A—N1A—C10A—C5A2.7 (4)C8B—N2B—C11B—C12B168.5 (3)
C15A—N1A—C10A—C5A178.5 (3)C14B—N2B—C11B—C12B55.1 (3)
C8A—C9A—C10A—N1A177.3 (3)C13B—N3B—C12B—C11B56.6 (3)
C8A—C9A—C10A—C5A2.6 (4)N2B—C11B—C12B—N3B57.4 (3)
C10A—N1A—C1A—C2A2.5 (5)C4B—C2B—C1B—N1B1.1 (5)
C15A—N1A—C1A—C2A178.8 (3)C3B—C2B—C1B—N1B179.1 (3)
N1A—C1A—C2A—C4A0.4 (5)C2B—C1B—N1B—C10B0.4 (5)
N1A—C1A—C2A—C3A179.1 (3)C2B—C1B—N1B—C15B179.0 (3)
C1A—C2A—C3A—O1A7.1 (5)C1B—N1B—C10B—C9B178.2 (3)
C4A—C2A—C3A—O1A173.4 (3)C15B—N1B—C10B—C9B2.4 (4)
C1A—C2A—C3A—O2A172.1 (3)C1B—N1B—C10B—C5B2.4 (4)
C4A—C2A—C3A—O2A7.4 (4)C15B—N1B—C10B—C5B176.9 (3)
C1A—N1A—C15A—C16A97.1 (3)C6B—C5B—C10B—N1B174.2 (3)
C10A—N1A—C15A—C16A81.7 (4)C4B—C5B—C10B—N1B3.1 (4)
N1A—C10A—C5A—C6A179.7 (3)C6B—C5B—C10B—C9B5.1 (4)
C9A—C10A—C5A—C6A0.2 (4)C4B—C5B—C10B—C9B177.5 (3)
N1A—C10A—C5A—C4A1.0 (4)C12B—N3B—C13B—C14B54.6 (3)
C9A—C10A—C5A—C4A178.9 (3)C8B—N2B—C14B—C13B169.3 (2)
C1A—C2A—C4A—O3A179.7 (3)C11B—N2B—C14B—C13B52.9 (3)
C3A—C2A—C4A—O3A0.3 (5)N3B—C13B—C14B—N2B53.1 (4)
C1A—C2A—C4A—C5A1.3 (4)N2B—C8B—C9B—C10B174.8 (3)
C3A—C2A—C4A—C5A179.2 (3)C7B—C8B—C9B—C10B0.8 (4)
C6A—C5A—C4A—O3A1.3 (4)N1B—C10B—C9B—C8B174.2 (3)
C10A—C5A—C4A—O3A180.0 (3)C5B—C10B—C9B—C8B5.1 (4)
C6A—C5A—C4A—C2A177.7 (3)C1B—N1B—C15B—C16B90.9 (4)
C10A—C5A—C4A—C2A1.0 (4)C10B—N1B—C15B—C16B89.7 (4)
C10A—C5A—C6A—C7A1.7 (4)O1X—C1X—C2X—O3X175.2 (2)
C4A—C5A—C6A—C7A177.0 (3)O2X—C1X—C2X—O3X5.1 (4)
C5A—C6A—C7A—F1A175.3 (3)O1X—C1X—C2X—C3X61.5 (4)
C5A—C6A—C7A—C8A1.3 (5)O2X—C1X—C2X—C3X118.1 (3)
C9A—C8A—C7A—C6A1.0 (4)O3X—C2X—C3X—O4X70.2 (3)
N2A—C8A—C7A—C6A174.2 (3)C1X—C2X—C3X—O4X53.1 (3)
C9A—C8A—C7A—F1A177.6 (2)O3X—C2X—C3X—C3Xii49.7 (4)
N2A—C8A—C7A—F1A2.3 (4)C1X—C2X—C3X—C3Xii173.0 (3)
C12A—N3A—C13A—C14A50.9 (4)O2Z—C1Z—C2Z—O3Z16.4 (4)
C8A—N2A—C14A—C13A159.1 (3)O1Z—C1Z—C2Z—O3Z165.8 (3)
C11A—N2A—C14A—C13A59.5 (3)O2Z—C1Z—C2Z—C3Z104.4 (4)
N3A—C13A—C14A—N2A53.7 (3)O1Z—C1Z—C2Z—C3Z73.4 (3)
O1B—C3B—C2B—C1B3.0 (5)O3Z—C2Z—C3Z—O4Z52.1 (3)
O2B—C3B—C2B—C1B177.3 (3)C1Z—C2Z—C3Z—O4Z68.3 (3)
O1B—C3B—C2B—C4B175.0 (4)O3Z—C2Z—C3Z—C3Ziii67.2 (4)
O2B—C3B—C2B—C4B4.7 (5)C1Z—C2Z—C3Z—C3Ziii172.3 (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) top
Crystal data top
C23H26FN3O7Z = 4
Mr = 475.47F(000) = 1000
Monoclinic, P21/cDx = 1.434 Mg m3
a = 8.0761 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.7184 (3) ŵ = 0.11 mm1
c = 18.7770 (4) ÅT = 100 K
β = 99.269 (1)°Block, colorless
V = 2202.83 (8) Å30.42 × 0.32 × 0.21 mm
Data collection top
CCD area detector
diffractometer
3253 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 25.0°, θmin = 1.8°
phi and ω scansh = 99
31912 measured reflectionsk = 1717
3883 independent reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0403P)2 + 0.9507P]
where P = (Fo2 + 2Fc2)/3
3883 reflections(Δ/σ)max = 0.001
328 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C23H26FN3O7V = 2202.83 (8) Å3
Mr = 475.47Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.0761 (2) ŵ = 0.11 mm1
b = 14.7184 (3) ÅT = 100 K
c = 18.7770 (4) Å0.42 × 0.32 × 0.21 mm
β = 99.269 (1)°
Data collection top
CCD area detector
diffractometer
3253 reflections with I > 2σ(I)
31912 measured reflectionsRint = 0.034
3883 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0330 restraints
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.21 e Å3
3883 reflectionsΔρmin = 0.25 e Å3
328 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.42326 (10)0.81417 (6)0.38762 (4)0.0202 (2)
O20.20034 (17)0.83988 (10)0.64181 (6)0.0432 (4)
H10.100 (3)0.8235 (16)0.6309 (13)0.065*
O10.42529 (15)0.91128 (9)0.58481 (6)0.0378 (3)
O30.04864 (13)0.81039 (7)0.57741 (5)0.0233 (3)
N30.30604 (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*
O1S0.30291 (15)0.44256 (9)0.34929 (6)0.0296 (3)
H1B0.333 (3)0.4109 (14)0.3878 (11)0.044*
H1A0.328 (3)0.4978 (15)0.3654 (11)0.044*
N20.23123 (15)0.86103 (8)0.25962 (6)0.0164 (3)
N10.22735 (15)0.91939 (8)0.39439 (6)0.0166 (3)
C120.39814 (18)0.78183 (10)0.18061 (7)0.0174 (3)
H120.49890.81490.20050.021*
H130.43110.72240.16540.021*
C30.2865 (2)0.88043 (12)0.58381 (9)0.0292 (4)
C20.19933 (19)0.88385 (10)0.52005 (8)0.0201 (3)
C40.03410 (19)0.84825 (10)0.52170 (8)0.0186 (3)
C50.03497 (18)0.85737 (9)0.45542 (7)0.0164 (3)
C60.20201 (18)0.83173 (10)0.45275 (8)0.0172 (3)
H90.27180.81280.49440.021*
C70.25997 (17)0.83500 (9)0.38897 (8)0.0165 (3)
C80.16021 (18)0.86086 (9)0.32319 (7)0.0155 (3)
C140.13694 (19)0.90895 (10)0.19760 (8)0.0199 (3)
H2'0.10040.96760.21280.024*
H1'0.03830.87410.17780.024*
C130.2475 (2)0.92176 (10)0.14082 (8)0.0202 (3)
H170.18540.95320.09960.024*
H160.34370.95880.16010.024*
C100.06431 (18)0.88930 (9)0.39175 (8)0.0158 (3)
C10.28645 (19)0.91834 (10)0.45688 (8)0.0186 (3)
H20.39270.94230.45770.022*
C150.33573 (18)0.95418 (10)0.32862 (8)0.0182 (3)
H30.45110.95620.33700.022*
H40.33040.91260.28900.022*
C160.2840 (2)1.04770 (10)0.30770 (8)0.0241 (4)
H50.28211.08830.34780.036*
H70.36281.06950.26750.036*
H60.17421.04480.29440.036*
C90.00224 (18)0.88868 (9)0.32601 (8)0.0163 (3)
H80.07110.90720.28400.020*
C110.28642 (18)0.77126 (10)0.23757 (8)0.0172 (3)
H110.18920.73490.21850.021*
H100.34740.74000.27920.021*
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)
H4'0.84070.87201.01940.020*
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)
H7'1.06590.85670.84370.021*
C5'0.81307 (19)0.84775 (10)0.82154 (8)0.0201 (3)
H6'0.80600.83980.77200.024*
C6'0.66806 (18)0.85010 (10)0.85203 (8)0.0194 (3)
H5'0.56400.84530.82270.023*
H140.380 (2)0.8405 (12)0.0816 (10)0.037 (5)*
H150.211 (2)0.7988 (12)0.0961 (10)0.032 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0133 (4)0.0278 (5)0.0200 (4)0.0019 (3)0.0040 (3)0.0019 (4)
O20.0363 (8)0.0793 (10)0.0165 (6)0.0269 (7)0.0117 (6)0.0132 (6)
O10.0320 (7)0.0593 (8)0.0255 (7)0.0200 (6)0.0146 (5)0.0078 (6)
O30.0225 (6)0.0353 (6)0.0120 (5)0.0082 (5)0.0023 (4)0.0025 (4)
N30.0156 (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)
O1S0.0340 (7)0.0324 (7)0.0220 (6)0.0021 (5)0.0031 (5)0.0001 (5)
N20.0181 (6)0.0181 (6)0.0138 (6)0.0031 (5)0.0052 (5)0.0019 (5)
N10.0163 (6)0.0195 (6)0.0143 (6)0.0017 (5)0.0033 (5)0.0001 (5)
C120.0159 (7)0.0191 (7)0.0172 (7)0.0020 (6)0.0029 (6)0.0005 (6)
C30.0283 (9)0.0421 (10)0.0182 (8)0.0103 (8)0.0070 (7)0.0025 (7)
C20.0209 (8)0.0254 (8)0.0150 (7)0.0038 (6)0.0054 (6)0.0014 (6)
C40.0208 (8)0.0210 (7)0.0137 (7)0.0004 (6)0.0020 (6)0.0025 (6)
C50.0179 (8)0.0170 (7)0.0143 (7)0.0002 (6)0.0024 (6)0.0011 (6)
C60.0172 (8)0.0192 (7)0.0143 (7)0.0008 (6)0.0004 (6)0.0009 (6)
C70.0121 (7)0.0176 (7)0.0204 (8)0.0002 (6)0.0044 (6)0.0011 (6)
C80.0175 (8)0.0139 (7)0.0158 (7)0.0015 (6)0.0043 (6)0.0007 (6)
C140.0210 (8)0.0215 (8)0.0181 (8)0.0058 (6)0.0059 (6)0.0038 (6)
C130.0239 (8)0.0199 (8)0.0180 (8)0.0036 (6)0.0066 (6)0.0028 (6)
C100.0164 (7)0.0142 (7)0.0170 (7)0.0003 (6)0.0036 (6)0.0015 (6)
C10.0183 (8)0.0208 (8)0.0178 (8)0.0024 (6)0.0062 (6)0.0021 (6)
C150.0163 (8)0.0233 (8)0.0147 (7)0.0034 (6)0.0018 (6)0.0012 (6)
C160.0268 (9)0.0229 (8)0.0229 (8)0.0053 (7)0.0048 (7)0.0028 (6)
C90.0182 (8)0.0164 (7)0.0141 (7)0.0007 (6)0.0014 (6)0.0010 (6)
C110.0180 (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) top
F1—C71.3580 (16)C6—H90.9300
O2—C31.335 (2)C7—C81.414 (2)
O2—H10.90 (3)C8—C91.384 (2)
O1—C31.212 (2)C14—C131.509 (2)
O3—C41.2752 (18)C14—H2'0.9700
N3—C121.4896 (18)C14—H1'0.9700
N3—C131.4928 (18)C13—H170.9700
N3—H140.98 (2)C13—H160.9700
N3—H150.940 (19)C10—C91.405 (2)
O2'—C7'1.2616 (17)C1—H20.9300
O1'—C7'1.2653 (17)C15—C161.509 (2)
O3'—C3'1.3535 (17)C15—H30.9700
O3'—H3'0.93 (2)C15—H40.9700
O1S—H1B0.86 (2)C16—H50.9600
O1S—H1A0.88 (2)C16—H70.9600
N2—C81.4050 (18)C16—H60.9600
N2—C141.4655 (18)C9—H80.9300
N2—C111.4749 (18)C11—H110.9700
N1—C11.3361 (18)C11—H100.9700
N1—C101.3976 (18)C7'—C1'1.505 (2)
N1—C151.4850 (18)C1'—C2'1.390 (2)
C12—C111.5142 (19)C1'—C6'1.393 (2)
C12—H120.9700C2'—C3'1.392 (2)
C12—H130.9700C2'—H4'0.9300
C3—C21.484 (2)C3'—C4'1.393 (2)
C2—C11.375 (2)C4'—C5'1.387 (2)
C2—C41.429 (2)C4'—H7'0.9300
C4—C51.450 (2)C5'—C6'1.384 (2)
C5—C101.409 (2)C5'—H6'0.9300
C5—C61.409 (2)C6'—H5'0.9300
C6—C71.355 (2)
C3—O2—H1107.8 (15)N3—C13—H16109.6
C12—N3—C13110.25 (11)C14—C13—H16109.6
C12—N3—H14109.4 (11)H17—C13—H16108.1
C13—N3—H14110.2 (11)N1—C10—C9120.31 (13)
C12—N3—H15110.5 (11)N1—C10—C5119.10 (12)
C13—N3—H15108.1 (11)C9—C10—C5120.57 (13)
H14—N3—H15108.5 (15)N1—C1—C2123.81 (14)
C3'—O3'—H3'110.4 (11)N1—C1—H2118.1
H1B—O1S—H1A101.2 (19)C2—C1—H2118.1
C8—N2—C14116.42 (11)N1—C15—C16112.35 (12)
C8—N2—C11114.84 (11)N1—C15—H3109.1
C14—N2—C11110.47 (11)C16—C15—H3109.1
C1—N1—C10119.96 (12)N1—C15—H4109.1
C1—N1—C15119.22 (12)C16—C15—H4109.1
C10—N1—C15120.81 (11)H3—C15—H4107.9
N3—C12—C11109.57 (11)C15—C16—H5109.5
N3—C12—H12109.8C15—C16—H7109.5
C11—C12—H12109.8H5—C16—H7109.5
N3—C12—H13109.8C15—C16—H6109.5
C11—C12—H13109.8H5—C16—H6109.5
H12—C12—H13108.2H7—C16—H6109.5
O1—C3—O2121.10 (15)C8—C9—C10120.68 (13)
O1—C3—C2124.02 (15)C8—C9—H8119.7
O2—C3—C2114.87 (14)C10—C9—H8119.7
C1—C2—C4120.00 (13)N2—C11—C12110.35 (11)
C1—C2—C3117.72 (14)N2—C11—H11109.6
C4—C2—C3122.18 (13)C12—C11—H11109.6
O3—C4—C2122.81 (13)N2—C11—H10109.6
O3—C4—C5121.43 (13)C12—C11—H10109.6
C2—C4—C5115.76 (13)H11—C11—H10108.1
C10—C5—C6118.44 (13)O2'—C7'—O1'124.75 (13)
C10—C5—C4120.95 (13)O2'—C7'—C1'117.99 (13)
C6—C5—C4120.57 (13)O1'—C7'—C1'117.26 (12)
C7—C6—C5119.39 (13)C2'—C1'—C6'119.39 (13)
C7—C6—H9120.3C2'—C1'—C7'120.33 (13)
C5—C6—H9120.3C6'—C1'—C7'120.26 (13)
C6—C7—F1118.89 (13)C1'—C2'—C3'120.31 (13)
C6—C7—C8123.52 (13)C1'—C2'—H4'119.8
F1—C7—C8117.58 (12)C3'—C2'—H4'119.8
C9—C8—N2123.46 (13)O3'—C3'—C2'117.71 (13)
C9—C8—C7117.17 (13)O3'—C3'—C4'122.36 (13)
N2—C8—C7119.31 (12)C2'—C3'—C4'119.93 (13)
N2—C14—C13109.32 (12)C5'—C4'—C3'119.66 (13)
N2—C14—H2'109.8C5'—C4'—H7'120.2
C13—C14—H2'109.8C3'—C4'—H7'120.2
N2—C14—H1'109.8C6'—C5'—C4'120.37 (14)
C13—C14—H1'109.8C6'—C5'—H6'119.8
H2'—C14—H1'108.3C4'—C5'—H6'119.8
N3—C13—C14110.38 (12)C5'—C6'—C1'120.30 (14)
N3—C13—H17109.6C5'—C6'—H5'119.9
C14—C13—H17109.6C1'—C6'—H5'119.9
C13—N3—C12—C1156.71 (15)C15—N1—C10—C5179.56 (12)
O1—C3—C2—C14.8 (3)C6—C5—C10—N1176.72 (13)
O2—C3—C2—C1175.03 (15)C4—C5—C10—N15.2 (2)
O1—C3—C2—C4178.68 (17)C6—C5—C10—C95.0 (2)
O2—C3—C2—C41.5 (2)C4—C5—C10—C9173.08 (13)
C1—C2—C4—O3175.59 (14)C10—N1—C1—C24.0 (2)
C3—C2—C4—O30.8 (2)C15—N1—C1—C2176.99 (14)
C1—C2—C4—C54.2 (2)C4—C2—C1—N11.5 (2)
C3—C2—C4—C5179.43 (14)C3—C2—C1—N1175.11 (14)
O3—C4—C5—C10172.34 (13)C1—N1—C15—C16104.83 (15)
C2—C4—C5—C107.4 (2)C10—N1—C15—C1674.17 (16)
O3—C4—C5—C65.7 (2)N2—C8—C9—C10178.18 (13)
C2—C4—C5—C6174.56 (13)C7—C8—C9—C101.1 (2)
C10—C5—C6—C72.6 (2)N1—C10—C9—C8178.59 (13)
C4—C5—C6—C7175.46 (13)C5—C10—C9—C83.1 (2)
C5—C6—C7—F1177.00 (12)C8—N2—C11—C12165.92 (12)
C5—C6—C7—C81.7 (2)C14—N2—C11—C1259.95 (15)
C14—N2—C8—C911.58 (19)N3—C12—C11—N257.74 (15)
C11—N2—C8—C9119.75 (15)O2'—C7'—C1'—C2'20.0 (2)
C14—N2—C8—C7165.48 (13)O1'—C7'—C1'—C2'160.21 (13)
C11—N2—C8—C763.19 (17)O2'—C7'—C1'—C6'161.42 (13)
C6—C7—C8—C93.5 (2)O1'—C7'—C1'—C6'18.4 (2)
F1—C7—C8—C9175.15 (12)C6'—C1'—C2'—C3'1.6 (2)
C6—C7—C8—N2179.21 (13)C7'—C1'—C2'—C3'177.04 (13)
F1—C7—C8—N22.10 (19)C1'—C2'—C3'—O3'178.50 (13)
C8—N2—C14—C13166.68 (12)C1'—C2'—C3'—C4'2.1 (2)
C11—N2—C14—C1359.99 (15)O3'—C3'—C4'—C5'179.89 (13)
C12—N3—C13—C1457.83 (16)C2'—C3'—C4'—C5'0.8 (2)
N2—C14—C13—N358.93 (16)C3'—C4'—C5'—C6'1.1 (2)
C1—N1—C10—C9178.87 (13)C4'—C5'—C6'—C1'1.7 (2)
C15—N1—C10—C92.1 (2)C2'—C1'—C6'—C5'0.4 (2)
C1—N1—C10—C50.6 (2)C7'—C1'—C6'—C5'178.97 (13)
(2013130_0m) top
Crystal data top
C21H30FN3O10SV = 1155.6 (5) Å3
Mr = 535.55Z = 2
Triclinic, P1F(000) = 564.0
a = 9.041 (3) ÅDx = 1.539 Mg m3
b = 10.767 (3) ÅMo Kα radiation, λ = 0.71073 Å
c = 12.438 (3) ŵ = 0.21 mm1
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 top
CCD area detector
diffractometer
2459 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.101
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
phi and ω scansh = 1010
15891 measured reflectionsk = 1212
4065 independent reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.08 w = 1/[σ2(Fo2) + (0.P)2 + 0.5688P]
where P = (Fo2 + 2Fc2)/3
4065 reflections(Δ/σ)max < 0.001
334 parametersΔρmax = 0.41 e Å3
22 restraintsΔρmin = 0.41 e Å3
Crystal data top
C21H30FN3O10Sγ = 74.64 (2)°
Mr = 535.55V = 1155.6 (5) Å3
Triclinic, P1Z = 2
a = 9.041 (3) ÅMo Kα radiation
b = 10.767 (3) ŵ = 0.21 mm1
c = 12.438 (3) ÅT = 100 K
α = 89.118 (19)°0.21 × 0.15 × 0.13 mm
β = 81.880 (17)°
Data collection top
CCD area detector
diffractometer
2459 reflections with I > 2σ(I)
15891 measured reflectionsRint = 0.101
4065 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04722 restraints
wR(F2) = 0.075H atoms treated by a mixture of independent and constrained refinement
S = 1.08Δρmax = 0.41 e Å3
4065 reflectionsΔρmin = 0.41 e Å3
334 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O1'0.6998 (2)0.00961 (19)0.80804 (15)0.0173 (5)
S10.78173 (9)0.11106 (8)0.79393 (6)0.0144 (2)
F10.36051 (18)0.45642 (16)0.13590 (12)0.0165 (4)
O1S0.3659 (2)0.57997 (19)0.32050 (15)0.0199 (5)
H1A0.33020.61330.26870.030*
H1B0.45130.59750.32340.030*
O4S0.6974 (2)0.01821 (19)0.45137 (16)0.0250 (6)
H4B0.62000.01980.41270.038*
H4A0.67760.01480.51020.038*
O10.3801 (2)0.3448 (2)0.36931 (16)0.0207 (5)
N30.2310 (3)0.2514 (3)0.4917 (2)0.0167 (7)
O20.1325 (2)0.40459 (19)0.39447 (15)0.0189 (5)
H10.04750.41180.35810.028*
O30.0763 (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)
C30.2410 (4)0.3633 (3)0.3335 (2)0.0164 (7)
C20.1857 (3)0.3414 (3)0.2191 (2)0.0116 (7)
C40.0253 (4)0.3795 (3)0.1784 (2)0.0130 (7)
C50.0191 (3)0.3617 (3)0.0657 (2)0.0106 (7)
C60.1745 (3)0.4073 (3)0.0164 (2)0.0122 (8)
H90.25120.44510.05830.015*
C70.2115 (3)0.3960 (3)0.0913 (2)0.0112 (7)
C80.1063 (4)0.3290 (3)0.1600 (2)0.0112 (7)
C140.0290 (3)0.2480 (3)0.3339 (2)0.0154 (8)
H180.06600.27290.31100.019*
H190.00840.15640.31920.019*
C130.0766 (3)0.2745 (3)0.4540 (2)0.0182 (8)
H160.00040.21930.49300.022*
H170.08070.36320.47030.022*
C110.3004 (3)0.2924 (3)0.3099 (2)0.0152 (8)
H110.29190.20150.29950.018*
H100.37810.34100.26790.018*
C120.3499 (3)0.3293 (3)0.4284 (2)0.0160 (8)
H130.35980.42030.43920.019*
H120.44960.31310.45280.019*
C100.0917 (3)0.3018 (3)0.0005 (2)0.0122 (7)
C90.0478 (3)0.2815 (3)0.1100 (2)0.0116 (7)
H80.12210.23570.15070.014*
N10.2482 (3)0.2619 (2)0.04663 (19)0.0110 (6)
C10.2894 (4)0.2845 (3)0.1512 (2)0.0128 (8)
H20.39410.26010.17920.015*
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)
H4'1.09940.06410.73170.016*
C5'1.2258 (4)0.0081 (3)0.8525 (2)0.0152 (8)
H5'1.32280.01760.81180.018*
C1'0.7855 (3)0.0421 (3)1.0410 (2)0.0145 (8)
H1'0.69560.07681.01060.017*
O3S0.4143 (2)0.0952 (2)0.35731 (15)0.0240 (6)
H3B0.36840.17160.36090.036*
H3A0.38280.06190.30510.036*
N20.1494 (3)0.3186 (2)0.27087 (18)0.0119 (6)
O2S0.2716 (2)0.35555 (19)0.38184 (15)0.0211 (6)
H2A0.23580.37230.45280.032*
H2B0.30460.41590.35670.032*
C150.3703 (3)0.1960 (3)0.0180 (2)0.0142 (8)
H30.46000.14820.03080.017*
H40.33250.13480.06470.017*
C160.4194 (3)0.2887 (3)0.0875 (2)0.0188 (8)
H70.46620.34430.04130.028*
H60.49280.24080.13170.028*
H50.33010.33960.13330.028*
H140.257 (3)0.274 (3)0.5600 (7)0.032 (11)*
H150.238 (4)0.162 (3)0.487 (3)0.057 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1'0.0207 (12)0.0185 (12)0.0179 (12)0.0105 (9)0.0102 (10)0.0023 (9)
S10.0150 (5)0.0159 (5)0.0137 (5)0.0049 (4)0.0055 (4)0.0011 (4)
F10.0093 (10)0.0216 (11)0.0165 (10)0.0015 (8)0.0002 (8)0.0019 (8)
O1S0.0171 (13)0.0242 (14)0.0198 (13)0.0055 (11)0.0080 (10)0.0040 (10)
O4S0.0266 (14)0.0315 (15)0.0212 (14)0.0145 (12)0.0044 (11)0.0035 (11)
O10.0190 (11)0.0300 (14)0.0149 (13)0.0111 (12)0.0004 (10)0.0004 (10)
N30.0154 (17)0.024 (2)0.0123 (18)0.0065 (14)0.0035 (14)0.0014 (14)
O20.0134 (13)0.0323 (15)0.0135 (13)0.0107 (11)0.0013 (10)0.0035 (10)
O30.0141 (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)
C30.0192 (13)0.0178 (18)0.0151 (18)0.0098 (16)0.0028 (15)0.0028 (14)
C20.0124 (19)0.0116 (19)0.0123 (19)0.0059 (15)0.0010 (15)0.0017 (14)
C40.0152 (17)0.0130 (18)0.0146 (18)0.0081 (13)0.0061 (12)0.0012 (13)
C50.0105 (18)0.0095 (19)0.0122 (18)0.0016 (14)0.0043 (15)0.0003 (14)
C60.0134 (19)0.0114 (19)0.0143 (19)0.0046 (15)0.0074 (15)0.0006 (14)
C70.0044 (18)0.0101 (19)0.018 (2)0.0013 (14)0.0002 (15)0.0045 (14)
C80.0155 (19)0.0096 (19)0.0111 (19)0.0065 (15)0.0042 (15)0.0030 (14)
C140.0125 (18)0.020 (2)0.0138 (19)0.0032 (16)0.0052 (15)0.0003 (15)
C130.016 (2)0.027 (2)0.0131 (19)0.0091 (16)0.0027 (15)0.0008 (15)
C110.0140 (19)0.021 (2)0.0130 (19)0.0077 (16)0.0033 (15)0.0007 (14)
C120.0110 (18)0.024 (2)0.0127 (19)0.0037 (16)0.0023 (15)0.0014 (15)
C100.0105 (19)0.0112 (19)0.0146 (19)0.0026 (15)0.0010 (15)0.0037 (14)
C90.0141 (19)0.0084 (19)0.0139 (19)0.0041 (15)0.0050 (15)0.0012 (14)
N10.0093 (15)0.0134 (16)0.0102 (15)0.0015 (12)0.0043 (12)0.0022 (12)
C10.0117 (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)
O3S0.0285 (14)0.0231 (14)0.0231 (14)0.0074 (11)0.0113 (11)0.0020 (11)
N20.0066 (14)0.0228 (17)0.0080 (15)0.0071 (12)0.0002 (12)0.0017 (12)
O2S0.0267 (14)0.0241 (14)0.0149 (13)0.0113 (11)0.0018 (11)0.0009 (10)
C150.0082 (18)0.020 (2)0.0122 (18)0.0002 (15)0.0023 (14)0.0023 (14)
C160.016 (2)0.022 (2)0.020 (2)0.0043 (16)0.0081 (15)0.0010 (15)
Geometric parameters (Å, º) top
O1'—S11.470 (2)C8—N21.390 (3)
S1—O3'1.453 (2)C8—C91.407 (4)
S1—O2'1.461 (2)C14—N21.470 (3)
S1—C3'1.794 (3)C14—C131.505 (4)
F1—C71.371 (3)C11—N21.481 (4)
O1—C31.238 (3)C11—C121.506 (4)
N3—C121.491 (4)C10—C91.394 (4)
N3—C131.492 (4)C10—N11.408 (4)
O2—C31.305 (3)N1—C11.337 (3)
O3—C41.290 (3)N1—C151.478 (3)
C3—C21.477 (4)C3'—C4'1.374 (4)
C2—C11.369 (4)C3'—C2'1.427 (4)
C2—C41.418 (4)C2'—C1'1.416 (4)
C4—C51.427 (4)C2'—C2'i1.425 (5)
C5—C101.404 (4)C4'—C5'1.408 (4)
C5—C61.411 (4)C5'—C1'i1.365 (4)
C6—C71.346 (4)C1'—C5'i1.365 (4)
C7—C81.416 (4)C15—C161.520 (4)
O3'—S1—O2'113.96 (12)N2—C14—C13111.8 (2)
O3'—S1—O1'112.66 (12)N3—C13—C14111.6 (2)
O2'—S1—O1'111.61 (12)N2—C11—C12110.6 (2)
O3'—S1—C3'105.74 (13)N3—C12—C11108.7 (2)
O2'—S1—C3'106.78 (12)C9—C10—C5120.9 (3)
O1'—S1—C3'105.34 (13)C9—C10—N1120.8 (3)
C12—N3—C13110.4 (3)C5—C10—N1118.3 (3)
O1—C3—O2122.1 (3)C10—C9—C8121.4 (3)
O1—C3—C2122.6 (3)C1—N1—C10120.2 (2)
O2—C3—C2115.3 (3)C1—N1—C15118.7 (2)
C1—C2—C4119.3 (3)C10—N1—C15121.1 (2)
C1—C2—C3120.1 (3)N1—C1—C2123.5 (3)
C4—C2—C3120.6 (3)C4'—C3'—C2'120.6 (3)
O3—C4—C2121.1 (3)C4'—C3'—S1117.5 (2)
O3—C4—C5121.3 (3)C2'—C3'—S1121.8 (2)
C2—C4—C5117.5 (3)C1'—C2'—C2'i118.9 (3)
C10—C5—C6117.9 (3)C1'—C2'—C3'122.6 (3)
C10—C5—C4120.9 (3)C2'i—C2'—C3'118.5 (3)
C6—C5—C4121.2 (3)C3'—C4'—C5'120.5 (3)
C7—C6—C5119.9 (3)C1'i—C5'—C4'120.2 (3)
C6—C7—F1116.8 (3)C5'i—C1'—C2'121.3 (3)
C6—C7—C8124.2 (3)C8—N2—C14117.4 (2)
F1—C7—C8119.0 (3)C8—N2—C11119.2 (2)
N2—C8—C9122.0 (3)C14—N2—C11111.1 (2)
N2—C8—C7122.5 (3)N1—C15—C16112.8 (2)
C9—C8—C7115.3 (3)
O1—C3—C2—C17.9 (5)C5—C10—N1—C11.9 (4)
O2—C3—C2—C1172.6 (3)C9—C10—N1—C150.8 (4)
O1—C3—C2—C4171.8 (3)C5—C10—N1—C15178.8 (3)
O2—C3—C2—C47.7 (4)C10—N1—C1—C22.5 (4)
C1—C2—C4—O3178.1 (3)C15—N1—C1—C2178.1 (3)
C3—C2—C4—O32.2 (4)C4—C2—C1—N10.0 (4)
C1—C2—C4—C53.0 (4)C3—C2—C1—N1179.7 (3)
C3—C2—C4—C5176.8 (3)O3'—S1—C3'—C4'1.7 (3)
O3—C4—C5—C10177.5 (3)O2'—S1—C3'—C4'120.0 (2)
C2—C4—C5—C103.5 (4)O1'—S1—C3'—C4'121.2 (2)
O3—C4—C5—C64.7 (4)O3'—S1—C3'—C2'176.6 (2)
C2—C4—C5—C6174.3 (3)O2'—S1—C3'—C2'61.7 (3)
C10—C5—C6—C71.9 (4)O1'—S1—C3'—C2'57.0 (3)
C4—C5—C6—C7176.0 (3)C4'—C3'—C2'—C1'178.6 (3)
C5—C6—C7—F1172.1 (2)S1—C3'—C2'—C1'3.2 (4)
C5—C6—C7—C86.4 (5)C4'—C3'—C2'—C2'i2.4 (5)
C6—C7—C8—N2179.5 (3)S1—C3'—C2'—C2'i175.8 (3)
F1—C7—C8—N22.0 (4)C2'—C3'—C4'—C5'1.8 (4)
C6—C7—C8—C95.0 (4)S1—C3'—C4'—C5'176.5 (2)
F1—C7—C8—C9173.5 (2)C3'—C4'—C5'—C1'i0.2 (4)
C12—N3—C13—C1455.6 (3)C2'i—C2'—C1'—C5'i1.1 (5)
N2—C14—C13—N352.8 (3)C3'—C2'—C1'—C5'i177.9 (3)
C13—N3—C12—C1159.0 (3)C9—C8—N2—C143.9 (4)
N2—C11—C12—N360.6 (3)C7—C8—N2—C14179.2 (3)
C6—C5—C10—C93.7 (4)C9—C8—N2—C11142.8 (3)
C4—C5—C10—C9178.4 (3)C7—C8—N2—C1142.0 (4)
C6—C5—C10—N1176.7 (3)C13—C14—N2—C8164.2 (3)
C4—C5—C10—N11.1 (4)C13—C14—N2—C1153.9 (3)
C5—C10—C9—C85.1 (4)C12—C11—N2—C8160.5 (3)
N1—C10—C9—C8175.4 (3)C12—C11—N2—C1458.3 (3)
N2—C8—C9—C10174.7 (3)C1—N1—C15—C1699.2 (3)
C7—C8—C9—C100.9 (4)C10—N1—C15—C1680.1 (3)
C9—C10—N1—C1178.5 (3)
Symmetry code: (i) x+2, y, z+2.
(2013176_0ma) top
Crystal data top
C26H23FN3O10SF(000) = 2440
Mr = 588.54Dx = 1.462 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
a = 11.6515 (3) ŵ = 0.19 mm1
b = 7.4209 (2) ÅT = 100 K
c = 61.8325 (18) ÅSheet, colourless
V = 5346.3 (3) Å30.30 × 0.04 × 0.03 mm
Z = 8
Data collection top
CCD area detector
diffractometer
5987 independent reflections
Radiation source: fine-focus sealed tube3739 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.103
phi and ω scansθmax = 27.5°, θmin = 0.7°
Absorption correction: empirical (using intensity measurements)
SADABS
h = 1214
Tmin = 0.948, Tmax = 0.995k = 99
47387 measured reflectionsl = 8073
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.12 w = 1/[σ2(Fo2) + (0.051P)2 + 7.5635P]
where P = (Fo2 + 2Fc2)/3
5987 reflections(Δ/σ)max < 0.001
419 parametersΔρmax = 0.43 e Å3
4 restraintsΔρmin = 0.40 e Å3
Crystal data top
C26H23FN3O10SV = 5346.3 (3) Å3
Mr = 588.54Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.6515 (3) ŵ = 0.19 mm1
b = 7.4209 (2) ÅT = 100 K
c = 61.8325 (18) Å0.30 × 0.04 × 0.03 mm
Data collection top
CCD area detector
diffractometer
5987 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS
3739 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.995Rint = 0.103
47387 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0684 restraints
wR(F2) = 0.164H atoms treated by a mixture of independent and constrained refinement
S = 1.12Δρmax = 0.43 e Å3
5987 reflectionsΔρmin = 0.40 e Å3
419 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S1'0.48089 (7)0.27147 (11)0.179103 (13)0.0196 (2)
F10.35001 (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)
C70.1635 (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)
H1'0.54760.35270.22210.020*
C4'0.2631 (3)0.1236 (4)0.22610 (5)0.0196 (7)
H4'0.19190.06730.22680.023*
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)
H3'0.27780.11100.19380.024*
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)
H6'0.19620.09750.26720.024*
C8'0.4314 (3)0.2900 (4)0.28304 (5)0.0219 (8)
H8'0.46870.32580.29560.026*
C2'0.4214 (3)0.2390 (4)0.20519 (5)0.0169 (7)
N20.1157 (3)0.3076 (4)0.11711 (4)0.0213 (6)
N30.0025 (3)0.2150 (4)0.15587 (5)0.0301 (8)
C9'0.4824 (3)0.3179 (4)0.26351 (5)0.0183 (7)
H9'0.55430.37200.26290.022*
C7'0.3230 (3)0.2076 (4)0.28433 (5)0.0225 (8)
H7'0.28890.19020.29780.027*
C90.3348 (3)0.4535 (5)0.07762 (5)0.0241 (8)
H90.41450.45530.07670.029*
C50.1493 (3)0.5138 (5)0.06240 (5)0.0239 (8)
O10.4300 (3)0.5791 (4)0.03843 (4)0.0468 (8)
N10.0811 (3)0.5803 (4)0.04557 (5)0.0334 (8)
C80.2835 (3)0.3896 (5)0.09580 (5)0.0222 (8)
C140.0070 (3)0.2688 (5)0.11660 (6)0.0285 (9)
H14A0.02750.21710.10270.034*
H14B0.05020.37940.11850.034*
C10.3225 (4)0.5815 (5)0.04072 (6)0.0300 (9)
O20.4042 (3)0.7186 (4)0.00143 (4)0.0530 (9)
H20.43350.67320.01220.080*
C60.0972 (3)0.4487 (4)0.08137 (5)0.0244 (8)
H60.01760.44860.08250.029*
C120.1201 (3)0.2678 (5)0.15635 (5)0.0254 (8)
H12A0.16770.16070.15550.031*
H12B0.13690.32790.16990.031*
O30.2300 (3)0.7879 (5)0.00994 (4)0.0551 (9)
C100.2685 (3)0.5164 (5)0.06037 (5)0.0241 (8)
C130.0360 (3)0.1380 (5)0.13452 (5)0.0292 (9)
H13A0.11780.11330.13440.035*
H13B0.00430.02530.13220.035*
C20.2474 (4)0.6479 (5)0.02445 (5)0.0294 (9)
C110.1482 (4)0.3922 (4)0.13774 (5)0.0276 (9)
H11A0.10700.50490.13950.033*
H11B0.22970.41840.13770.033*
C40.1317 (4)0.6449 (5)0.02762 (6)0.0325 (10)
H40.08490.69030.01670.039*
C30.2915 (4)0.7227 (6)0.00377 (6)0.0396 (11)
C150.0474 (4)0.5874 (8)0.04713 (7)0.0520 (14)
O2S0.8206 (11)0.768 (3)0.11484 (18)0.120 (6)0.61 (4)
O4S0.6648 (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)
O3S0.722 (2)0.055 (2)0.0921 (2)0.073 (8)0.42 (5)
C160.0964 (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)
O1S0.7765 (2)0.4094 (4)0.15897 (4)0.0376 (7)
H1B0.71440.42370.16490.056*
H1A0.80950.51000.16340.056*
H1010.018 (4)0.133 (5)0.1655 (6)0.074 (17)*
H1000.042 (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 (Å2) top
U11U22U33U12U13U23
S1'0.0206 (5)0.0208 (4)0.0175 (4)0.0030 (3)0.0005 (4)0.0032 (3)
F10.0293 (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)
C70.028 (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)
N20.0257 (18)0.0252 (15)0.0131 (14)0.0035 (13)0.0007 (12)0.0017 (11)
N30.040 (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)
C90.024 (2)0.0290 (19)0.0188 (18)0.0047 (16)0.0044 (16)0.0010 (14)
C50.033 (2)0.0246 (18)0.0140 (17)0.0026 (15)0.0047 (16)0.0014 (13)
O10.0344 (19)0.073 (2)0.0326 (16)0.0078 (16)0.0090 (14)0.0164 (15)
N10.037 (2)0.044 (2)0.0193 (16)0.0025 (16)0.0009 (15)0.0095 (14)
C80.028 (2)0.0240 (18)0.0146 (17)0.0017 (15)0.0050 (15)0.0003 (13)
C140.028 (2)0.037 (2)0.0206 (18)0.0008 (17)0.0061 (16)0.0078 (15)
C10.038 (3)0.032 (2)0.0200 (19)0.0062 (18)0.0027 (18)0.0004 (15)
O20.055 (2)0.074 (2)0.0296 (16)0.0059 (18)0.0098 (15)0.0195 (15)
C60.027 (2)0.0266 (18)0.0197 (18)0.0045 (15)0.0015 (16)0.0019 (14)
C120.041 (2)0.0208 (17)0.0144 (17)0.0015 (16)0.0022 (15)0.0007 (13)
O30.069 (2)0.071 (2)0.0254 (16)0.0153 (18)0.0114 (16)0.0220 (15)
C100.034 (2)0.0237 (18)0.0146 (17)0.0056 (16)0.0032 (16)0.0005 (13)
C130.026 (2)0.039 (2)0.0225 (19)0.0008 (17)0.0067 (17)0.0071 (16)
C20.044 (3)0.0283 (19)0.0157 (18)0.0016 (18)0.0019 (18)0.0030 (14)
C110.049 (3)0.0199 (17)0.0136 (17)0.0003 (16)0.0023 (17)0.0012 (13)
C40.051 (3)0.032 (2)0.0155 (18)0.0009 (19)0.0041 (18)0.0044 (15)
C30.057 (3)0.039 (2)0.023 (2)0.001 (2)0.008 (2)0.0054 (17)
C150.028 (3)0.093 (4)0.035 (3)0.003 (3)0.008 (2)0.023 (3)
O2S0.093 (7)0.214 (14)0.054 (6)0.006 (9)0.023 (5)0.038 (8)
O4S0.043 (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)
O3S0.041 (11)0.138 (15)0.039 (6)0.001 (7)0.004 (6)0.007 (6)
C160.033 (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)
O1S0.0274 (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) top
S1'—O1'1.450 (2)N3—C121.481 (5)
S1'—O2'1.458 (2)N3—C131.491 (5)
S1'—O3'1.471 (2)C9—C81.358 (5)
S1'—C2'1.772 (3)C9—C101.398 (5)
F1—C81.360 (4)C5—C101.395 (5)
C7—C61.391 (5)C5—N11.399 (4)
C7—N21.404 (4)C5—C61.406 (5)
C7—C81.409 (5)O1—C11.260 (5)
C1'—C2'1.358 (4)N1—C41.345 (4)
C1'—C10'1.428 (4)N1—C151.501 (5)
C4'—C3'1.371 (4)C14—C131.512 (5)
C4'—C5'1.419 (4)C1—C21.422 (5)
C5'—C6'1.422 (5)C1—C101.452 (5)
C5'—C10'1.424 (4)O2—C31.321 (5)
C3'—C2'1.416 (4)C12—C111.511 (4)
C10'—C9'1.416 (4)O3—C31.211 (5)
C6'—C7'1.360 (5)C2—C41.362 (6)
C8'—C9'1.362 (5)C2—C31.486 (5)
C8'—C7'1.406 (5)C15—C161.338 (10)
N2—C141.459 (5)C15—C16'1.367 (12)
N2—C111.471 (4)
O1'—S1'—O2'113.45 (15)C10—C5—N1119.6 (3)
O1'—S1'—O3'112.31 (14)C10—C5—C6120.6 (3)
O2'—S1'—O3'111.68 (14)N1—C5—C6119.8 (3)
O1'—S1'—C2'106.68 (15)C4—N1—C5119.4 (3)
O2'—S1'—C2'106.03 (14)C4—N1—C15118.5 (3)
O3'—S1'—C2'106.05 (14)C5—N1—C15122.1 (3)
C6—C7—N2122.9 (3)C9—C8—F1119.0 (3)
C6—C7—C8117.1 (3)C9—C8—C7122.8 (3)
N2—C7—C8119.9 (3)F1—C8—C7118.1 (3)
C2'—C1'—C10'120.1 (3)N2—C14—C13109.3 (3)
C3'—C4'—C5'120.9 (3)O1—C1—C2122.5 (3)
C4'—C5'—C6'122.0 (3)O1—C1—C10121.4 (3)
C4'—C5'—C10'119.0 (3)C2—C1—C10116.1 (4)
C6'—C5'—C10'119.0 (3)C7—C6—C5120.7 (3)
C4'—C3'—C2'119.6 (3)N3—C12—C11110.8 (3)
C9'—C10'—C5'118.6 (3)C5—C10—C9118.5 (3)
C9'—C10'—C1'122.5 (3)C5—C10—C1120.8 (3)
C5'—C10'—C1'118.9 (3)C9—C10—C1120.7 (3)
C7'—C6'—C5'120.4 (3)N3—C13—C14110.1 (3)
C9'—C8'—C7'120.5 (3)C4—C2—C1120.1 (3)
C1'—C2'—C3'121.5 (3)C4—C2—C3118.2 (4)
C1'—C2'—S1'121.5 (3)C1—C2—C3121.7 (4)
C3'—C2'—S1'117.1 (2)N2—C11—C12110.1 (3)
C7—N2—C14116.8 (3)N1—C4—C2123.9 (4)
C7—N2—C11116.0 (3)O3—C3—O2121.4 (4)
C14—N2—C11110.8 (3)O3—C3—C2123.2 (4)
C12—N3—C13111.8 (3)O2—C3—C2115.5 (4)
C8'—C9'—C10'120.8 (3)C16—C15—C16'127.9 (7)
C6'—C7'—C8'120.6 (3)C16—C15—N1112.4 (6)
C8—C9—C10120.3 (3)C16'—C15—N1117.3 (6)
(2013329_0m) top
Crystal data top
C23H26FN3O7V = 1136.71 (10) Å3
Mr = 475.47Z = 2
Triclinic, P1F(000) = 500.0
a = 7.0237 (4) ÅDx = 1.389 Mg m3
b = 9.9645 (5) ÅMo Kα radiation, λ = 0.71073 Å
c = 17.4655 (9) ŵ = 0.11 mm1
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 top
CCD area detector
diffractometer
5221 independent reflections
Radiation source: fine-focus sealed tube2989 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
phi and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: empirical (using intensity measurements)
SADABS
h = 99
Tmin = 0.984, Tmax = 0.997k = 1212
17531 measured reflectionsl = 2222
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0513P)2 + 0.0507P]
where P = (Fo2 + 2Fc2)/3
5221 reflections(Δ/σ)max = 0.003
322 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.20 e Å3
Crystal data top
C23H26FN3O7γ = 109.906 (3)°
Mr = 475.47V = 1136.71 (10) Å3
Triclinic, P1Z = 2
a = 7.0237 (4) ÅMo Kα radiation
b = 9.9645 (5) ŵ = 0.11 mm1
c = 17.4655 (9) ÅT = 296 K
α = 91.100 (3)°0.15 × 0.06 × 0.03 mm
β = 97.543 (3)°
Data collection top
CCD area detector
diffractometer
5221 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS
2989 reflections with I > 2σ(I)
Tmin = 0.984, Tmax = 0.997Rint = 0.029
17531 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.17 e Å3
5221 reflectionsΔρmin = 0.20 e Å3
322 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.82208 (17)0.33285 (9)0.61457 (6)0.0581 (3)
O20.54571 (18)0.03225 (15)0.27079 (7)0.0529 (3)
H20.553 (3)0.051 (2)0.2947 (12)0.079*
O1S0.2611 (3)0.0897 (2)0.04954 (10)0.0715 (4)
O10.6433 (2)0.26226 (14)0.30653 (7)0.0662 (4)
O30.61812 (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)
N10.78967 (19)0.19248 (12)0.53606 (7)0.0349 (3)
N20.93994 (19)0.11350 (13)0.73272 (7)0.0383 (3)
N31.0486 (2)0.15138 (14)0.89301 (7)0.0438 (4)
H151.13610.17070.92980.053*
H140.94860.13740.91590.053*
C30.6252 (2)0.1420 (2)0.32344 (10)0.0450 (4)
C20.6840 (2)0.10546 (17)0.40286 (9)0.0360 (4)
C10.7373 (2)0.20978 (16)0.46120 (9)0.0373 (4)
H10.73740.29990.44820.045*
C100.7977 (2)0.05996 (15)0.55761 (8)0.0312 (3)
C90.8576 (2)0.03828 (16)0.63500 (9)0.0339 (4)
H80.89270.11390.67230.041*
C80.8660 (2)0.09337 (16)0.65762 (9)0.0343 (4)
C111.0267 (3)0.01119 (17)0.78827 (9)0.0446 (4)
H110.91690.03550.80630.054*
H101.10850.09230.76310.054*
C121.1588 (3)0.01935 (18)0.85661 (9)0.0467 (4)
H131.27950.02920.83940.056*
H121.20370.06110.89490.056*
C40.6764 (2)0.03538 (17)0.42026 (9)0.0353 (4)
C50.7397 (2)0.05309 (16)0.50056 (9)0.0328 (4)
C60.7441 (2)0.18632 (16)0.52364 (9)0.0368 (4)
H90.70290.26380.48720.044*
C70.8070 (2)0.20340 (16)0.59774 (9)0.0377 (4)
C140.8209 (3)0.23983 (18)0.77048 (10)0.0500 (5)
H180.76140.32110.73280.060*
H190.71040.22080.79120.060*
C130.9586 (3)0.27426 (18)0.83510 (10)0.0525 (5)
H160.88030.35770.85960.063*
H171.06690.29590.81420.063*
C150.8401 (3)0.31597 (16)0.59305 (10)0.0441 (4)
H40.79440.28190.64140.053*
H30.76750.37870.57400.053*
C161.0657 (3)0.3989 (2)0.60746 (12)0.0631 (6)
H71.13730.33870.62910.095*
H61.09200.48000.64300.095*
H51.11190.43120.55950.095*
C5'0.3426 (4)0.4400 (2)0.87721 (14)0.0801 (7)
H4'0.25190.47620.89700.096*
C6'0.4481 (3)0.3696 (2)0.92331 (12)0.0623 (5)
H5'0.42670.35760.97450.075*
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)
H3'0.30540.50350.76970.095*
C3'0.5051 (4)0.4027 (2)0.77122 (12)0.0679 (6)
H2'0.52120.41210.71940.081*
H1A0.376 (4)0.137 (3)0.0435 (16)0.108 (11)*
H1B0.243 (4)0.001 (3)0.0584 (15)0.114 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0853 (8)0.0407 (5)0.0530 (7)0.0318 (5)0.0017 (5)0.0053 (5)
O20.0554 (8)0.0678 (9)0.0296 (7)0.0154 (6)0.0015 (5)0.0057 (6)
O1S0.0715 (12)0.0779 (11)0.0821 (12)0.0398 (10)0.0305 (9)0.0228 (9)
O10.0796 (9)0.0619 (9)0.0480 (8)0.0185 (7)0.0085 (7)0.0210 (7)
O30.0570 (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)
N10.0394 (7)0.0341 (7)0.0302 (8)0.0123 (6)0.0021 (6)0.0043 (6)
N20.0430 (8)0.0374 (7)0.0303 (8)0.0114 (6)0.0036 (6)0.0067 (6)
N30.0463 (8)0.0594 (9)0.0304 (8)0.0256 (7)0.0011 (6)0.0093 (7)
C30.0366 (9)0.0580 (11)0.0355 (10)0.0103 (8)0.0035 (7)0.0095 (9)
C20.0309 (8)0.0451 (9)0.0288 (9)0.0094 (7)0.0026 (6)0.0066 (7)
C10.0360 (9)0.0391 (9)0.0352 (10)0.0110 (7)0.0036 (7)0.0101 (7)
C100.0294 (8)0.0334 (8)0.0299 (9)0.0095 (6)0.0043 (6)0.0050 (7)
C90.0343 (8)0.0364 (8)0.0294 (9)0.0110 (7)0.0029 (6)0.0019 (7)
C80.0313 (8)0.0392 (9)0.0317 (9)0.0120 (7)0.0019 (6)0.0063 (7)
C110.0556 (11)0.0424 (9)0.0324 (10)0.0145 (8)0.0008 (8)0.0043 (7)
C120.0492 (10)0.0546 (10)0.0301 (10)0.0120 (8)0.0003 (8)0.0037 (8)
C40.0298 (8)0.0431 (9)0.0305 (9)0.0095 (7)0.0044 (7)0.0005 (8)
C50.0291 (8)0.0390 (8)0.0303 (9)0.0118 (7)0.0040 (6)0.0036 (7)
C60.0383 (9)0.0363 (8)0.0339 (10)0.0120 (7)0.0022 (7)0.0030 (7)
C70.0402 (9)0.0324 (8)0.0415 (10)0.0150 (7)0.0023 (7)0.0052 (7)
C140.0539 (11)0.0479 (10)0.0385 (10)0.0084 (8)0.0037 (8)0.0134 (8)
C130.0707 (12)0.0468 (10)0.0380 (11)0.0214 (9)0.0029 (9)0.0094 (8)
C150.0612 (11)0.0350 (9)0.0381 (10)0.0214 (8)0.0009 (8)0.0007 (7)
C160.0714 (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) top
F1—C71.3640 (17)C11—H110.9700
O2—C31.328 (2)C11—H100.9700
O2—H20.95 (2)C12—H130.9700
O1S—H1A0.80 (3)C12—H120.9700
O1S—H1B0.89 (3)C4—C51.447 (2)
O1—C31.208 (2)C5—C61.404 (2)
O3—C41.2601 (17)C6—C71.345 (2)
O3'—C2'1.352 (2)C6—H90.9300
O3'—H1'0.97 (3)C14—C131.510 (2)
O2'—C7'1.258 (2)C14—H180.9700
O1'—C7'1.253 (2)C14—H190.9700
N1—C11.3418 (18)C13—H160.9700
N1—C101.3974 (18)C13—H170.9700
N1—C151.4812 (19)C15—C161.500 (3)
N2—C81.3903 (18)C15—H40.9700
N2—C111.463 (2)C15—H30.9700
N2—C141.476 (2)C16—H70.9600
N3—C131.476 (2)C16—H60.9600
N3—C121.484 (2)C16—H50.9600
N3—H150.9000C5'—C4'1.379 (3)
N3—H140.9000C5'—C6'1.382 (3)
C3—C21.483 (2)C5'—H4'0.9300
C2—C11.361 (2)C6'—C1'1.386 (3)
C2—C41.426 (2)C6'—H5'0.9300
C1—H10.9300C1'—C2'1.398 (2)
C10—C51.402 (2)C1'—C7'1.493 (2)
C10—C91.405 (2)C2'—C3'1.387 (3)
C9—C81.395 (2)C4'—C3'1.354 (3)
C9—H80.9300C4'—H3'0.9300
C8—C71.414 (2)C3'—H2'0.9300
C11—C121.515 (2)
C3—O2—H2108.0 (13)C7—C6—C5120.87 (14)
H1A—O1S—H1B114 (3)C7—C6—H9119.6
C2'—O3'—H1'104.9 (16)C5—C6—H9119.6
C1—N1—C10119.23 (13)C6—C7—F1117.43 (14)
C1—N1—C15118.55 (12)C6—C7—C8123.65 (14)
C10—N1—C15122.21 (12)F1—C7—C8118.87 (14)
C8—N2—C11118.27 (12)N2—C14—C13109.84 (14)
C8—N2—C14118.60 (12)N2—C14—H18109.7
C11—N2—C14110.54 (13)C13—C14—H18109.7
C13—N3—C12111.16 (13)N2—C14—H19109.7
C13—N3—H15109.4C13—C14—H19109.7
C12—N3—H15109.4H18—C14—H19108.2
C13—N3—H14109.4N3—C13—C14109.97 (14)
C12—N3—H14109.4N3—C13—H16109.7
H15—N3—H14108.0C14—C13—H16109.7
O1—C3—O2120.98 (16)N3—C13—H17109.7
O1—C3—C2123.45 (16)C14—C13—H17109.7
O2—C3—C2115.55 (15)H16—C13—H17108.2
C1—C2—C4119.56 (14)N1—C15—C16111.80 (14)
C1—C2—C3117.94 (15)N1—C15—H4109.3
C4—C2—C3122.41 (14)C16—C15—H4109.3
N1—C1—C2124.95 (14)N1—C15—H3109.3
N1—C1—H1117.5C16—C15—H3109.3
C2—C1—H1117.5H4—C15—H3107.9
N1—C10—C5118.62 (13)C15—C16—H7109.5
N1—C10—C9121.15 (13)C15—C16—H6109.5
C5—C10—C9120.20 (13)H7—C16—H6109.5
C8—C9—C10121.96 (14)C15—C16—H5109.5
C8—C9—H8119.0H7—C16—H5109.5
C10—C9—H8119.0H6—C16—H5109.5
N2—C8—C9122.61 (14)C4'—C5'—C6'118.6 (2)
N2—C8—C7121.77 (13)C4'—C5'—H4'120.7
C9—C8—C7115.49 (14)C6'—C5'—H4'120.7
N2—C11—C12110.59 (13)C5'—C6'—C1'121.4 (2)
N2—C11—H11109.5C5'—C6'—H5'119.3
C12—C11—H11109.5C1'—C6'—H5'119.3
N2—C11—H10109.5C6'—C1'—C2'118.57 (17)
C12—C11—H10109.5C6'—C1'—C7'120.57 (17)
H11—C11—H10108.1C2'—C1'—C7'120.84 (18)
N3—C12—C11112.33 (13)O3'—C2'—C3'118.51 (19)
N3—C12—H13109.1O3'—C2'—C1'121.81 (16)
C11—C12—H13109.1C3'—C2'—C1'119.7 (2)
N3—C12—H12109.1O1'—C7'—O2'122.89 (16)
C11—C12—H12109.1O1'—C7'—C1'119.16 (17)
H13—C12—H12107.9O2'—C7'—C1'117.94 (17)
O3—C4—C2122.77 (14)C3'—C4'—C5'121.5 (2)
O3—C4—C5121.69 (14)C3'—C4'—H3'119.3
C2—C4—C5115.54 (13)C5'—C4'—H3'119.3
C10—C5—C6117.79 (14)C4'—C3'—C2'120.3 (2)
C10—C5—C4121.94 (13)C4'—C3'—H2'119.8
C6—C5—C4120.26 (14)C2'—C3'—H2'119.8
O1—C3—C2—C18.3 (2)C2—C4—C5—C102.1 (2)
O2—C3—C2—C1170.36 (14)O3—C4—C5—C62.1 (2)
O1—C3—C2—C4174.96 (16)C2—C4—C5—C6178.06 (14)
O2—C3—C2—C46.4 (2)C10—C5—C6—C71.7 (2)
C10—N1—C1—C22.0 (2)C4—C5—C6—C7178.48 (14)
C15—N1—C1—C2178.85 (15)C5—C6—C7—F1175.05 (14)
C4—C2—C1—N11.6 (2)C5—C6—C7—C82.2 (2)
C3—C2—C1—N1178.50 (14)N2—C8—C7—C6176.70 (15)
C1—N1—C10—C53.4 (2)C9—C8—C7—C60.8 (2)
C15—N1—C10—C5177.49 (14)N2—C8—C7—F10.5 (2)
C1—N1—C10—C9178.11 (13)C9—C8—C7—F1176.40 (14)
C15—N1—C10—C91.0 (2)C8—N2—C14—C13157.90 (14)
N1—C10—C9—C8179.83 (14)C11—N2—C14—C1360.81 (19)
C5—C10—C9—C81.4 (2)C12—N3—C13—C1455.73 (19)
C11—N2—C8—C94.9 (2)N2—C14—C13—N359.7 (2)
C14—N2—C8—C9133.47 (16)C1—N1—C15—C1693.40 (17)
C11—N2—C8—C7170.78 (15)C10—N1—C15—C1685.68 (18)
C14—N2—C8—C750.9 (2)C4'—C5'—C6'—C1'0.6 (3)
C10—C9—C8—N2174.89 (13)C5'—C6'—C1'—C2'0.4 (3)
C10—C9—C8—C71.0 (2)C5'—C6'—C1'—C7'179.03 (18)
C8—N2—C11—C12161.49 (14)C6'—C1'—C2'—O3'179.05 (17)
C14—N2—C11—C1257.07 (18)C7'—C1'—C2'—O3'2.3 (3)
C13—N3—C12—C1152.96 (19)C6'—C1'—C2'—C3'1.0 (3)
N2—C11—C12—N353.34 (19)C7'—C1'—C2'—C3'177.68 (16)
C1—C2—C4—O3176.24 (14)C6'—C1'—C7'—O1'1.4 (3)
C3—C2—C4—O30.5 (2)C2'—C1'—C7'—O1'177.18 (15)
C1—C2—C4—C53.6 (2)C6'—C1'—C7'—O2'179.73 (17)
C3—C2—C4—C5179.71 (13)C2'—C1'—C7'—O2'1.7 (2)
N1—C10—C5—C6178.50 (13)C6'—C5'—C4'—C3'0.5 (3)
C9—C10—C5—C60.0 (2)C5'—C4'—C3'—C2'1.9 (3)
N1—C10—C5—C41.3 (2)O3'—C2'—C3'—C4'177.92 (19)
C9—C10—C5—C4179.79 (13)C1'—C2'—C3'—C4'2.1 (3)
O3—C4—C5—C10177.68 (14)
(mo_2014070_0m) top
Crystal data top
C23H26FN3O7V = 3394.48 (14) Å3
Mr = 475.47Z = 6
Triclinic, P1F(000) = 1500.0
a = 7.3258 (2) ÅDx = 1.396 Mg m3
b = 19.8297 (4) ÅMo Kα radiation, λ = 0.71073 Å
c = 23.9108 (5) ŵ = 0.11 mm1
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 top
CCD area detector
diffractometer
15579 independent reflections
Radiation source: fine-focus sealed tube7689 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.047
phi and ω scansθmax = 27.6°, θmin = 1.7°
Absorption correction: empirical (using intensity measurements)
SADABS
h = 99
Tmin = 0.938, Tmax = 0.991k = 2525
49327 measured reflectionsl = 3131
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.95 w = 1/[σ2(Fo2) + (0.0525P)2]
where P = (Fo2 + 2Fc2)/3
15579 reflections(Δ/σ)max = 0.001
972 parametersΔρmax = 0.18 e Å3
3 restraintsΔρmin = 0.19 e Å3
Crystal data top
C23H26FN3O7γ = 96.143 (1)°
Mr = 475.47V = 3394.48 (14) Å3
Triclinic, P1Z = 6
a = 7.3258 (2) ÅMo Kα radiation
b = 19.8297 (4) ŵ = 0.11 mm1
c = 23.9108 (5) ÅT = 296 K
α = 96.924 (1)°0.60 × 0.15 × 0.08 mm
β = 97.210 (1)°
Data collection top
CCD area detector
diffractometer
15579 independent reflections
Absorption correction: empirical (using intensity measurements)
SADABS
7689 reflections with I > 2σ(I)
Tmin = 0.938, Tmax = 0.991Rint = 0.047
49327 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0493 restraints
wR(F2) = 0.122H atoms treated by a mixture of independent and constrained refinement
S = 0.95Δρmax = 0.18 e Å3
15579 reflectionsΔρmin = 0.19 e Å3
972 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F1A0.7955 (2)1.07985 (6)0.11286 (5)0.0629 (4)
F1B0.7742 (2)0.23097 (6)0.17775 (5)0.0674 (4)
F1C0.61707 (19)0.44309 (5)0.52686 (5)0.0591 (4)
O1S0.4439 (3)0.93045 (9)0.35161 (7)0.0573 (5)
O2A0.6976 (2)1.00321 (8)0.20252 (6)0.0585 (4)
H20.697 (4)1.0320 (11)0.1691 (8)0.088*
O2S0.2387 (3)0.41258 (9)0.97820 (7)0.0597 (5)
O1A0.7431 (3)0.89563 (9)0.22413 (7)0.0895 (7)
O3S0.9420 (3)0.75184 (9)0.30124 (8)0.0638 (5)
O3A0.7047 (2)1.05282 (7)0.09915 (6)0.0545 (4)
N3B0.8813 (3)0.44907 (10)0.07972 (7)0.0402 (4)
O3B0.9994 (2)0.25550 (7)0.38534 (6)0.0614 (5)
O1B1.0983 (3)0.41470 (9)0.51593 (7)0.0781 (6)
O1X0.38485 (19)0.59125 (7)0.01692 (5)0.0461 (4)
O3X0.6899 (2)0.64382 (8)0.28104 (6)0.0542 (4)
H370.770 (4)0.6763 (12)0.2844 (11)0.081*
O2X0.1774 (2)0.52359 (7)0.05002 (6)0.0509 (4)
O2C0.2724 (2)0.39749 (8)0.21771 (6)0.0583 (4)
H420.302 (4)0.4248 (12)0.2540 (11)0.087*
O1C0.2573 (2)0.28815 (8)0.18309 (6)0.0663 (5)
O3C0.3857 (2)0.43833 (7)0.32027 (6)0.0548 (4)
O2Y1.1302 (2)0.14711 (8)0.61848 (6)0.0560 (4)
O3Y0.6980 (2)0.03789 (7)0.37222 (6)0.0472 (4)
H610.607 (3)0.0013 (11)0.3662 (9)0.071*
O1Y0.9277 (2)0.06708 (7)0.63958 (5)0.0523 (4)
O2Z0.5014 (2)0.84186 (8)0.25919 (6)0.0592 (4)
O3Z0.0121 (2)0.69531 (7)0.03106 (6)0.0555 (4)
H660.067 (4)0.6616 (12)0.0297 (10)0.083*
O1Z0.3153 (2)0.76659 (7)0.29379 (6)0.0511 (4)
N3A0.8493 (2)0.91589 (9)0.25997 (7)0.0478 (5)
H14A0.90850.91940.29570.057*
H15A0.74010.88950.25790.057*
N2A0.8444 (2)0.95121 (8)0.14637 (6)0.0392 (4)
N1A0.7837 (2)0.86367 (8)0.05532 (6)0.0420 (4)
O2B1.0967 (3)0.30424 (9)0.48763 (7)0.0695 (5)
H201.079 (4)0.2755 (12)0.4556 (9)0.104*
N2B0.7197 (2)0.35753 (8)0.14918 (6)0.0407 (4)
N1B0.8951 (2)0.44633 (8)0.35144 (7)0.0388 (4)
N1C0.4645 (2)0.24137 (7)0.34275 (6)0.0348 (4)
N2C0.6529 (2)0.31159 (8)0.54633 (6)0.0396 (4)
N3C0.4594 (2)0.21423 (8)0.60513 (6)0.0408 (4)
H14C0.36260.18250.60610.049*
H15C0.53330.21890.63880.049*
C12A0.8158 (4)0.98485 (11)0.24622 (8)0.0579 (7)
H150.93261.01450.25150.069*
H160.73661.00460.27170.069*
C11A0.7250 (3)0.97978 (11)0.18559 (8)0.0511 (6)
H170.60720.95080.18050.061*
H90.70101.02490.17710.061*
C8A0.8067 (3)0.95979 (10)0.08890 (8)0.0353 (5)
C9A0.8022 (3)0.90672 (10)0.04483 (8)0.0382 (5)
H190.81510.86290.05360.046*
C10A0.7788 (3)0.91744 (9)0.01227 (8)0.0352 (5)
C5A0.7522 (3)0.98208 (10)0.02700 (8)0.0361 (5)
C4A0.7292 (3)0.99433 (10)0.08589 (8)0.0397 (5)
C2A0.7393 (3)0.93709 (10)0.12678 (8)0.0419 (5)
C3A0.7267 (3)0.94249 (13)0.18859 (9)0.0541 (6)
C15A0.8012 (4)0.79303 (10)0.04313 (9)0.0576 (7)
H60.88960.79450.00910.069*
H70.84840.76790.07440.069*
C16A0.6184 (4)0.75643 (12)0.03486 (12)0.0956 (10)
H40.57130.78130.00390.143*
H30.63500.71120.02630.143*
H50.53210.75330.06900.143*
C1A0.7636 (3)0.87525 (10)0.10978 (8)0.0466 (6)
H80.76650.83860.13770.056*
C13A0.9623 (3)0.88374 (11)0.21982 (8)0.0483 (6)
H140.97290.83720.22720.058*
H131.08610.90860.22630.058*
C14A0.8807 (3)0.88270 (10)0.15856 (8)0.0453 (5)
H120.96590.86550.13400.054*
H110.76580.85190.15040.054*
C7A0.7826 (3)1.02465 (10)0.07221 (8)0.0416 (5)
C6A0.7539 (3)1.03562 (10)0.01707 (8)0.0418 (5)
H180.73511.07910.00840.050*
C3B1.0677 (3)0.36715 (14)0.47835 (10)0.0535 (6)
C2B0.9971 (3)0.37282 (11)0.41794 (8)0.0414 (5)
C4B0.9691 (3)0.31477 (10)0.37511 (9)0.0410 (5)
C5B0.9022 (3)0.32714 (9)0.31833 (8)0.0364 (5)
C6B0.8707 (3)0.27313 (10)0.27308 (9)0.0438 (5)
H290.89100.22920.27990.053*
C7B0.8111 (3)0.28471 (10)0.21980 (9)0.0430 (5)
C8B0.7801 (3)0.35017 (10)0.20572 (8)0.0367 (5)
C11B0.8294 (3)0.33375 (10)0.10531 (8)0.0463 (6)
H350.74750.31760.07000.056*
H340.89060.29560.11680.056*
C12B0.9719 (3)0.38935 (10)0.09551 (8)0.0427 (5)
H361.06020.40310.12980.051*
H211.03890.37250.06530.051*
C10B0.8659 (3)0.39229 (9)0.30657 (8)0.0330 (5)
C1B0.9602 (3)0.43522 (11)0.40400 (8)0.0437 (5)
H220.98150.47230.43280.052*
C15B0.8701 (3)0.51756 (9)0.34208 (9)0.0497 (6)
H260.85080.54350.37750.060*
H270.76100.51720.31440.060*
C16B1.0380 (4)0.55186 (12)0.32087 (13)0.0881 (9)
H251.14610.55220.34820.132*
H241.01960.59810.31580.132*
H231.05470.52710.28520.132*
C9B0.8051 (3)0.40279 (9)0.25048 (8)0.0359 (5)
H280.78110.44630.24330.043*
C14B0.6382 (3)0.41886 (10)0.13656 (8)0.0440 (5)
H320.57700.43540.16830.053*
H330.54460.40690.10330.053*
C13B0.7786 (3)0.47590 (10)0.12564 (8)0.0423 (5)
H310.71570.51380.11430.051*
H300.86430.49240.16010.051*
C7X0.3180 (3)0.56731 (10)0.05772 (8)0.0352 (5)
C1X0.4142 (3)0.58990 (9)0.11700 (7)0.0313 (4)
C2X0.3723 (3)0.55389 (9)0.16120 (8)0.0386 (5)
H410.28030.51660.15390.046*
C3X0.4649 (3)0.57256 (10)0.21558 (8)0.0415 (5)
H400.43650.54760.24460.050*
C4X0.6000 (3)0.62839 (10)0.22693 (8)0.0377 (5)
C5X0.6410 (3)0.66594 (9)0.18382 (8)0.0366 (5)
H380.73030.70410.19160.044*
C6X0.5491 (3)0.64641 (9)0.12956 (8)0.0353 (5)
H390.57780.67150.10070.042*
C3C0.2952 (3)0.33294 (12)0.22322 (9)0.0459 (5)
C2C0.3684 (3)0.32204 (10)0.28185 (8)0.0363 (5)
C1C0.3980 (3)0.25718 (10)0.29165 (8)0.0384 (5)
H600.37050.22210.26120.046*
C10C0.5016 (3)0.29211 (9)0.38985 (8)0.0317 (4)
C9C0.5623 (3)0.27622 (9)0.44424 (8)0.0348 (5)
H530.58230.23140.44830.042*
C8C0.5931 (3)0.32498 (9)0.49173 (8)0.0339 (5)
C11C0.5491 (3)0.33348 (10)0.59265 (8)0.0485 (6)
H450.50090.37590.58600.058*
H460.63210.34200.62840.058*
C12C0.3911 (3)0.28006 (10)0.59678 (8)0.0459 (6)
H470.32780.29520.62840.055*
H480.30290.27410.56220.055*
C5C0.4741 (3)0.35960 (9)0.38255 (8)0.0339 (5)
C4C0.4074 (3)0.37672 (10)0.32706 (8)0.0379 (5)
C6C0.5134 (3)0.41005 (9)0.43020 (8)0.0390 (5)
H540.49950.45540.42620.047*
C7C0.5714 (3)0.39293 (9)0.48187 (8)0.0397 (5)
C14C0.7174 (3)0.24567 (10)0.55397 (8)0.0435 (5)
H520.80770.25160.58810.052*
H510.77940.23090.52190.052*
C13C0.5643 (3)0.19066 (10)0.55886 (8)0.0437 (5)
H490.48150.18010.52310.052*
H500.61650.14930.56690.052*
C15C0.4871 (3)0.16892 (9)0.34791 (8)0.0423 (5)
H580.59960.16710.37350.051*
H590.50010.14530.31090.051*
C16C0.3241 (4)0.13275 (10)0.37001 (10)0.0622 (7)
H570.31360.15490.40720.093*
H550.34260.08590.37210.093*
H560.21250.13450.34470.093*
C7Y0.9997 (3)0.09965 (10)0.60404 (8)0.0384 (5)
C1Y0.9214 (3)0.08205 (9)0.54257 (8)0.0322 (5)
C6Y0.7878 (3)0.02642 (9)0.52425 (8)0.0353 (5)
H620.74890.00100.55050.042*
C5Y0.7110 (3)0.01073 (9)0.46794 (8)0.0366 (5)
H630.62040.02670.45660.044*
C4Y0.7690 (3)0.05086 (9)0.42805 (8)0.0342 (5)
C2Y0.9784 (3)0.12140 (9)0.50220 (8)0.0380 (5)
H651.06970.15860.51350.046*
C3Y0.9027 (3)0.10658 (9)0.44579 (8)0.0394 (5)
H640.94160.13410.41960.047*
C7Z0.3736 (3)0.79272 (10)0.25281 (8)0.0393 (5)
C1Z0.2806 (3)0.76558 (9)0.19395 (8)0.0330 (5)
C2Z0.3154 (3)0.79869 (9)0.14779 (8)0.0404 (5)
H690.40150.83780.15350.048*
C3Z0.2257 (3)0.77513 (10)0.09373 (8)0.0426 (5)
H700.24990.79840.06340.051*
C4Z0.0996 (3)0.71671 (9)0.08486 (8)0.0362 (5)
C6Z0.1533 (3)0.70685 (9)0.18404 (8)0.0360 (5)
H670.12850.68350.21430.043*
C5Z0.0633 (3)0.68257 (9)0.13014 (8)0.0368 (5)
H680.02180.64320.12420.044*
H14B0.796 (3)0.4345 (10)0.0462 (9)0.052 (6)*
H15B0.971 (3)0.4808 (10)0.0721 (8)0.047 (6)*
H2B0.218 (4)0.4477 (13)0.9989 (11)0.080 (9)*
H2A0.360 (5)0.4091 (14)0.9835 (12)0.108 (12)*
H3A0.920 (4)0.7864 (10)0.3238 (9)0.078 (9)*
H3B1.061 (4)0.7537 (13)0.2991 (11)0.089 (10)*
H1A0.455 (4)0.9007 (13)0.3230 (11)0.089 (10)*
H1B0.320 (5)0.9350 (15)0.3499 (12)0.119 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0962 (11)0.0471 (7)0.0435 (7)0.0130 (7)0.0104 (7)0.0055 (6)
F1B0.1064 (12)0.0407 (7)0.0514 (8)0.0019 (7)0.0083 (8)0.0009 (6)
F1C0.0921 (11)0.0382 (6)0.0436 (7)0.0070 (7)0.0042 (7)0.0021 (6)
O1S0.0518 (12)0.0613 (11)0.0502 (11)0.0064 (10)0.0035 (9)0.0116 (8)
O2A0.0585 (11)0.0766 (12)0.0440 (9)0.0067 (9)0.0033 (8)0.0278 (8)
O2S0.0439 (12)0.0601 (11)0.0668 (12)0.0042 (10)0.0107 (9)0.0178 (9)
O1A0.157 (2)0.0713 (12)0.0333 (9)0.0029 (12)0.0057 (11)0.0026 (9)
O3S0.0543 (13)0.0644 (12)0.0636 (12)0.0106 (10)0.0136 (10)0.0169 (9)
O3A0.0684 (12)0.0502 (9)0.0478 (9)0.0113 (8)0.0029 (8)0.0201 (7)
N3B0.0370 (11)0.0538 (11)0.0277 (10)0.0042 (10)0.0003 (9)0.0102 (9)
O3B0.0784 (13)0.0513 (9)0.0611 (10)0.0195 (9)0.0060 (9)0.0280 (8)
O1B0.0996 (16)0.0926 (13)0.0394 (10)0.0176 (12)0.0063 (10)0.0099 (10)
O1X0.0399 (9)0.0633 (9)0.0319 (8)0.0042 (8)0.0002 (7)0.0083 (7)
O3X0.0616 (12)0.0602 (10)0.0330 (8)0.0071 (8)0.0068 (8)0.0016 (7)
O2X0.0383 (9)0.0642 (9)0.0418 (9)0.0131 (8)0.0026 (7)0.0064 (7)
O2C0.0677 (12)0.0632 (11)0.0458 (9)0.0117 (9)0.0035 (9)0.0238 (8)
O1C0.0868 (14)0.0721 (11)0.0373 (9)0.0110 (10)0.0034 (9)0.0080 (8)
O3C0.0730 (12)0.0447 (9)0.0501 (9)0.0166 (8)0.0020 (8)0.0185 (7)
O2Y0.0407 (10)0.0722 (10)0.0446 (9)0.0166 (9)0.0030 (7)0.0106 (8)
O3Y0.0554 (10)0.0541 (9)0.0288 (8)0.0006 (8)0.0005 (7)0.0040 (7)
O1Y0.0475 (10)0.0735 (10)0.0317 (8)0.0075 (8)0.0003 (7)0.0094 (7)
O2Z0.0451 (10)0.0720 (10)0.0494 (9)0.0182 (9)0.0034 (7)0.0105 (8)
O3Z0.0661 (12)0.0570 (10)0.0348 (8)0.0077 (8)0.0099 (8)0.0039 (8)
O1Z0.0474 (10)0.0686 (10)0.0321 (8)0.0038 (8)0.0035 (7)0.0057 (7)
N3A0.0418 (11)0.0717 (12)0.0284 (9)0.0044 (10)0.0033 (8)0.0121 (9)
N2A0.0401 (11)0.0525 (10)0.0274 (9)0.0137 (9)0.0056 (8)0.0067 (8)
N1A0.0563 (12)0.0380 (9)0.0295 (9)0.0027 (9)0.0007 (8)0.0045 (8)
O2B0.0798 (13)0.0786 (13)0.0549 (11)0.0207 (11)0.0036 (10)0.0322 (9)
N2B0.0457 (11)0.0475 (10)0.0302 (9)0.0053 (9)0.0076 (8)0.0088 (8)
N1B0.0444 (11)0.0401 (9)0.0332 (10)0.0084 (8)0.0043 (8)0.0094 (8)
N1C0.0415 (11)0.0355 (9)0.0289 (9)0.0070 (8)0.0069 (8)0.0069 (7)
N2C0.0457 (11)0.0440 (10)0.0299 (9)0.0048 (9)0.0047 (8)0.0091 (8)
N3C0.0367 (11)0.0542 (11)0.0286 (9)0.0046 (9)0.0019 (8)0.0092 (8)
C12A0.0705 (18)0.0692 (16)0.0358 (13)0.0102 (14)0.0159 (12)0.0045 (11)
C11A0.0498 (15)0.0697 (15)0.0388 (13)0.0193 (13)0.0135 (11)0.0093 (11)
C8A0.0316 (12)0.0450 (12)0.0296 (11)0.0044 (10)0.0022 (9)0.0083 (9)
C9A0.0441 (14)0.0398 (11)0.0309 (11)0.0042 (10)0.0034 (10)0.0080 (9)
C10A0.0351 (12)0.0376 (11)0.0321 (11)0.0015 (10)0.0041 (9)0.0054 (9)
C5A0.0336 (12)0.0414 (11)0.0325 (11)0.0022 (10)0.0008 (9)0.0083 (9)
C4A0.0383 (13)0.0440 (12)0.0371 (12)0.0004 (10)0.0027 (10)0.0138 (10)
C2A0.0449 (14)0.0465 (12)0.0318 (11)0.0035 (11)0.0005 (10)0.0089 (10)
C3A0.0599 (17)0.0619 (16)0.0376 (14)0.0058 (13)0.0003 (12)0.0137 (12)
C15A0.093 (2)0.0394 (12)0.0417 (13)0.0164 (14)0.0039 (13)0.0069 (10)
C16A0.107 (3)0.0622 (17)0.105 (2)0.0318 (17)0.0184 (19)0.0330 (16)
C1A0.0564 (16)0.0477 (13)0.0321 (12)0.0015 (11)0.0027 (11)0.0013 (10)
C13A0.0436 (14)0.0666 (14)0.0383 (12)0.0092 (12)0.0076 (11)0.0176 (11)
C14A0.0500 (15)0.0560 (13)0.0331 (12)0.0145 (12)0.0062 (10)0.0110 (10)
C7A0.0454 (14)0.0424 (12)0.0361 (12)0.0072 (11)0.0067 (10)0.0008 (10)
C6A0.0445 (14)0.0405 (11)0.0420 (13)0.0077 (10)0.0052 (10)0.0111 (10)
C3B0.0473 (15)0.0736 (17)0.0445 (15)0.0116 (14)0.0077 (12)0.0231 (13)
C2B0.0351 (13)0.0557 (13)0.0369 (12)0.0095 (11)0.0052 (10)0.0165 (11)
C4B0.0334 (13)0.0489 (13)0.0458 (13)0.0073 (11)0.0081 (10)0.0217 (11)
C5B0.0341 (12)0.0387 (11)0.0396 (12)0.0052 (10)0.0086 (10)0.0133 (10)
C6B0.0503 (15)0.0356 (11)0.0490 (14)0.0068 (11)0.0104 (11)0.0154 (10)
C7B0.0521 (15)0.0349 (11)0.0420 (13)0.0015 (11)0.0110 (11)0.0040 (10)
C8B0.0350 (13)0.0418 (12)0.0355 (12)0.0020 (10)0.0111 (10)0.0100 (9)
C11B0.0587 (16)0.0482 (12)0.0313 (11)0.0043 (12)0.0095 (11)0.0011 (10)
C12B0.0428 (14)0.0583 (13)0.0279 (11)0.0086 (12)0.0079 (10)0.0041 (10)
C10B0.0286 (12)0.0374 (11)0.0349 (11)0.0033 (9)0.0089 (9)0.0092 (9)
C1B0.0444 (14)0.0508 (13)0.0358 (12)0.0063 (11)0.0045 (10)0.0064 (10)
C15B0.0653 (17)0.0370 (12)0.0450 (13)0.0137 (12)0.0030 (12)0.0034 (10)
C16B0.074 (2)0.0508 (15)0.135 (3)0.0094 (15)0.0122 (18)0.0342 (16)
C9B0.0376 (13)0.0384 (11)0.0354 (12)0.0055 (10)0.0096 (10)0.0141 (9)
C14B0.0380 (13)0.0612 (14)0.0359 (12)0.0104 (12)0.0055 (10)0.0148 (10)
C13B0.0481 (14)0.0470 (12)0.0348 (12)0.0083 (11)0.0092 (10)0.0116 (10)
C7X0.0298 (12)0.0401 (11)0.0341 (12)0.0048 (10)0.0018 (9)0.0012 (9)
C1X0.0276 (11)0.0337 (10)0.0315 (11)0.0041 (9)0.0042 (9)0.0001 (8)
C2X0.0363 (13)0.0370 (11)0.0396 (12)0.0011 (10)0.0026 (10)0.0014 (9)
C3X0.0479 (14)0.0421 (12)0.0333 (12)0.0009 (11)0.0029 (10)0.0094 (9)
C4X0.0407 (13)0.0419 (11)0.0271 (11)0.0056 (11)0.0020 (9)0.0026 (9)
C5X0.0360 (13)0.0345 (10)0.0359 (12)0.0020 (10)0.0042 (10)0.0014 (9)
C6X0.0367 (12)0.0365 (11)0.0328 (11)0.0045 (10)0.0051 (9)0.0048 (9)
C3C0.0425 (14)0.0565 (14)0.0427 (14)0.0062 (12)0.0092 (11)0.0198 (12)
C2C0.0327 (12)0.0450 (12)0.0340 (11)0.0063 (10)0.0053 (9)0.0138 (10)
C1C0.0383 (13)0.0466 (12)0.0311 (11)0.0049 (10)0.0074 (9)0.0061 (9)
C10C0.0322 (12)0.0341 (10)0.0306 (11)0.0045 (9)0.0098 (9)0.0058 (9)
C9C0.0408 (13)0.0326 (10)0.0347 (11)0.0090 (10)0.0105 (9)0.0101 (9)
C8C0.0353 (12)0.0377 (11)0.0303 (11)0.0038 (10)0.0096 (9)0.0068 (9)
C11C0.0696 (17)0.0460 (12)0.0281 (11)0.0027 (12)0.0087 (11)0.0000 (9)
C12C0.0493 (15)0.0589 (14)0.0324 (12)0.0114 (12)0.0137 (10)0.0051 (10)
C5C0.0349 (12)0.0369 (11)0.0338 (11)0.0107 (10)0.0091 (9)0.0102 (9)
C4C0.0361 (13)0.0409 (12)0.0408 (12)0.0080 (10)0.0095 (10)0.0152 (10)
C6C0.0471 (14)0.0321 (11)0.0410 (12)0.0110 (10)0.0103 (10)0.0084 (9)
C7C0.0509 (14)0.0332 (11)0.0342 (12)0.0050 (10)0.0098 (10)0.0018 (9)
C14C0.0413 (14)0.0558 (13)0.0380 (12)0.0110 (11)0.0067 (10)0.0188 (10)
C13C0.0546 (15)0.0448 (12)0.0338 (12)0.0089 (11)0.0082 (11)0.0097 (9)
C15C0.0589 (16)0.0341 (11)0.0362 (12)0.0124 (11)0.0091 (11)0.0052 (9)
C16C0.0749 (19)0.0434 (13)0.0689 (17)0.0002 (13)0.0129 (14)0.0143 (12)
C7Y0.0293 (12)0.0482 (12)0.0363 (12)0.0055 (11)0.0044 (10)0.0001 (10)
C1Y0.0276 (11)0.0360 (11)0.0320 (11)0.0043 (9)0.0036 (9)0.0011 (9)
C6Y0.0360 (12)0.0374 (11)0.0319 (11)0.0008 (10)0.0058 (9)0.0044 (9)
C5Y0.0365 (12)0.0352 (10)0.0349 (12)0.0022 (10)0.0023 (9)0.0003 (9)
C4Y0.0362 (12)0.0361 (11)0.0309 (11)0.0087 (10)0.0056 (9)0.0017 (9)
C2Y0.0323 (12)0.0362 (11)0.0427 (12)0.0026 (10)0.0039 (10)0.0014 (9)
C3Y0.0411 (13)0.0404 (11)0.0374 (12)0.0002 (10)0.0066 (10)0.0106 (9)
C7Z0.0316 (13)0.0471 (12)0.0356 (12)0.0034 (11)0.0013 (10)0.0037 (10)
C1Z0.0290 (12)0.0345 (10)0.0342 (11)0.0064 (9)0.0018 (9)0.0003 (9)
C2Z0.0401 (13)0.0360 (11)0.0433 (13)0.0004 (10)0.0041 (10)0.0044 (10)
C3Z0.0478 (14)0.0466 (12)0.0334 (12)0.0050 (11)0.0014 (10)0.0112 (10)
C4Z0.0384 (13)0.0361 (11)0.0314 (11)0.0053 (10)0.0021 (9)0.0005 (9)
C6Z0.0402 (13)0.0369 (11)0.0304 (11)0.0046 (10)0.0048 (9)0.0030 (9)
C5Z0.0360 (12)0.0330 (10)0.0393 (12)0.0001 (10)0.0053 (10)0.0003 (9)
Geometric parameters (Å, º) top
F1A—C7A1.360 (2)C3B—C2B1.493 (3)
F1B—C7B1.353 (2)C2B—C1B1.365 (3)
F1C—C7C1.356 (2)C2B—C4B1.424 (3)
O1S—H1A0.87 (3)C4B—C5B1.443 (3)
O1S—H1B0.92 (3)C5B—C10B1.401 (2)
O2A—C3A1.319 (3)C5B—C6B1.406 (3)
O2A—H20.925 (16)C6B—C7B1.348 (3)
O2S—H2B0.84 (2)C6B—H290.9300
O2S—H2A0.89 (3)C7B—C8B1.414 (3)
O1A—C3A1.208 (2)C8B—C9B1.381 (2)
O3S—H3A0.861 (16)C11B—C12B1.496 (3)
O3S—H3B0.87 (3)C11B—H350.9700
O3A—C4A1.264 (2)C11B—H340.9700
N3B—C12B1.483 (2)C12B—H360.9700
N3B—C13B1.486 (2)C12B—H210.9700
N3B—H14B0.95 (2)C10B—C9B1.406 (2)
N3B—H15B0.91 (2)C1B—H220.9300
O3B—C4B1.266 (2)C15B—C16B1.514 (3)
O1B—C3B1.203 (3)C15B—H260.9700
O1X—C7X1.264 (2)C15B—H270.9700
O3X—C4X1.360 (2)C16B—H250.9600
O3X—H370.81 (2)C16B—H240.9600
O2X—C7X1.253 (2)C16B—H230.9600
O2C—C3C1.328 (2)C9B—H280.9300
O2C—H420.95 (2)C14B—C13B1.514 (3)
O1C—C3C1.209 (2)C14B—H320.9700
O3C—C4C1.276 (2)C14B—H330.9700
O2Y—C7Y1.251 (2)C13B—H310.9700
O3Y—C4Y1.354 (2)C13B—H300.9700
O3Y—H610.92 (2)C7X—C1X1.495 (3)
O1Y—C7Y1.261 (2)C1X—C6X1.389 (2)
O2Z—C7Z1.258 (2)C1X—C2X1.392 (2)
O3Z—C4Z1.360 (2)C2X—C3X1.377 (3)
O3Z—H660.83 (3)C2X—H410.9300
O1Z—C7Z1.262 (2)C3X—C4X1.380 (3)
N3A—C13A1.476 (2)C3X—H400.9300
N3A—C12A1.482 (2)C4X—C5X1.387 (2)
N3A—H14A0.9000C5X—C6X1.375 (2)
N3A—H15A0.9000C5X—H380.9300
N2A—C8A1.402 (2)C6X—H390.9300
N2A—C11A1.467 (2)C3C—C2C1.486 (3)
N2A—C14A1.468 (2)C2C—C1C1.370 (2)
N1A—C1A1.342 (2)C2C—C4C1.414 (3)
N1A—C10A1.397 (2)C1C—H600.9300
N1A—C15A1.480 (2)C10C—C5C1.403 (2)
O2B—C3B1.327 (3)C10C—C9C1.404 (2)
O2B—H200.884 (16)C9C—C8C1.378 (2)
N2B—C8B1.399 (2)C9C—H530.9300
N2B—C14B1.458 (2)C8C—C7C1.418 (2)
N2B—C11B1.464 (2)C11C—C12C1.504 (3)
N1B—C1B1.340 (2)C11C—H450.9700
N1B—C10B1.400 (2)C11C—H460.9700
N1B—C15B1.483 (2)C12C—H470.9700
N1C—C1C1.343 (2)C12C—H480.9700
N1C—C10C1.395 (2)C5C—C6C1.401 (2)
N1C—C15C1.481 (2)C5C—C4C1.448 (3)
N2C—C8C1.390 (2)C6C—C7C1.350 (3)
N2C—C14C1.461 (2)C6C—H540.9300
N2C—C11C1.470 (2)C14C—C13C1.505 (3)
N3C—C12C1.474 (2)C14C—H520.9700
N3C—C13C1.483 (2)C14C—H510.9700
N3C—H14C0.9000C13C—H490.9700
N3C—H15C0.9000C13C—H500.9700
C12A—C11A1.504 (3)C15C—C16C1.512 (3)
C12A—H150.9700C15C—H580.9700
C12A—H160.9700C15C—H590.9700
C11A—H170.9700C16C—H570.9600
C11A—H90.9700C16C—H550.9600
C8A—C9A1.391 (2)C16C—H560.9600
C8A—C7A1.414 (3)C7Y—C1Y1.494 (3)
C9A—C10A1.399 (2)C1Y—C6Y1.383 (3)
C9A—H190.9300C1Y—C2Y1.389 (2)
C10A—C5A1.397 (2)C6Y—C5Y1.377 (2)
C5A—C6A1.401 (3)C6Y—H620.9300
C5A—C4A1.450 (3)C5Y—C4Y1.391 (2)
C4A—C2A1.421 (3)C5Y—H630.9300
C2A—C1A1.360 (3)C4Y—C3Y1.383 (3)
C2A—C3A1.487 (3)C2Y—C3Y1.377 (3)
C15A—C16A1.501 (4)C2Y—H650.9300
C15A—H60.9700C3Y—H640.9300
C15A—H70.9700C7Z—C1Z1.494 (3)
C16A—H40.9600C1Z—C2Z1.387 (2)
C16A—H30.9600C1Z—C6Z1.388 (3)
C16A—H50.9600C2Z—C3Z1.377 (3)
C1A—H80.9300C2Z—H690.9300
C13A—C14A1.508 (3)C3Z—C4Z1.379 (3)
C13A—H140.9700C3Z—H700.9300
C13A—H130.9700C4Z—C5Z1.383 (2)
C14A—H120.9700C6Z—C5Z1.377 (3)
C14A—H110.9700C6Z—H670.9300
C7A—C6A1.356 (3)C5Z—H680.9300
C6A—H180.9300
H1A—O1S—H1B107 (3)N1B—C15B—H27109.4
C3A—O2A—H2107.4 (15)C16B—C15B—H27109.4
H2B—O2S—H2A109 (3)H26—C15B—H27108.0
H3A—O3S—H3B110 (2)C15B—C16B—H25109.5
C12B—N3B—C13B110.50 (15)C15B—C16B—H24109.5
C12B—N3B—H14B108.3 (12)H25—C16B—H24109.5
C13B—N3B—H14B108.7 (12)C15B—C16B—H23109.5
C12B—N3B—H15B107.4 (12)H25—C16B—H23109.5
C13B—N3B—H15B113.0 (12)H24—C16B—H23109.5
H14B—N3B—H15B108.8 (17)C8B—C9B—C10B121.72 (17)
C4X—O3X—H37112.3 (18)C8B—C9B—H28119.1
C3C—O2C—H42109.2 (15)C10B—C9B—H28119.1
C4Y—O3Y—H61110.1 (14)N2B—C14B—C13B113.45 (17)
C4Z—O3Z—H66112.0 (18)N2B—C14B—H32108.9
C13A—N3A—C12A110.30 (15)C13B—C14B—H32108.9
C13A—N3A—H14A109.6N2B—C14B—H33108.9
C12A—N3A—H14A109.6C13B—C14B—H33108.9
C13A—N3A—H15A109.6H32—C14B—H33107.7
C12A—N3A—H15A109.6N3B—C13B—C14B108.80 (16)
H14A—N3A—H15A108.1N3B—C13B—H31109.9
C8A—N2A—C11A117.89 (16)C14B—C13B—H31109.9
C8A—N2A—C14A116.72 (15)N3B—C13B—H30109.9
C11A—N2A—C14A110.05 (15)C14B—C13B—H30109.9
C1A—N1A—C10A119.41 (16)H31—C13B—H30108.3
C1A—N1A—C15A118.47 (16)O2X—C7X—O1X122.22 (18)
C10A—N1A—C15A122.05 (15)O2X—C7X—C1X118.81 (18)
C3B—O2B—H20111.6 (18)O1X—C7X—C1X118.93 (18)
C8B—N2B—C14B119.44 (15)C6X—C1X—C2X118.06 (17)
C8B—N2B—C11B118.55 (17)C6X—C1X—C7X121.40 (17)
C14B—N2B—C11B111.52 (15)C2X—C1X—C7X120.53 (17)
C1B—N1B—C10B119.82 (16)C3X—C2X—C1X121.12 (18)
C1B—N1B—C15B118.03 (17)C3X—C2X—H41119.4
C10B—N1B—C15B121.98 (15)C1X—C2X—H41119.4
C1C—N1C—C10C119.88 (15)C2X—C3X—C4X119.79 (18)
C1C—N1C—C15C118.37 (16)C2X—C3X—H40120.1
C10C—N1C—C15C121.68 (15)C4X—C3X—H40120.1
C8C—N2C—C14C119.24 (15)O3X—C4X—C3X117.46 (18)
C8C—N2C—C11C118.87 (17)O3X—C4X—C5X122.45 (18)
C14C—N2C—C11C110.05 (15)C3X—C4X—C5X120.08 (17)
C12C—N3C—C13C111.29 (14)C6X—C5X—C4X119.63 (18)
C12C—N3C—H14C109.4C6X—C5X—H38120.2
C13C—N3C—H14C109.4C4X—C5X—H38120.2
C12C—N3C—H15C109.4C5X—C6X—C1X121.29 (18)
C13C—N3C—H15C109.4C5X—C6X—H39119.4
H14C—N3C—H15C108.0C1X—C6X—H39119.4
N3A—C12A—C11A109.92 (18)O1C—C3C—O2C121.24 (19)
N3A—C12A—H15109.7O1C—C3C—C2C124.5 (2)
C11A—C12A—H15109.7O2C—C3C—C2C114.2 (2)
N3A—C12A—H16109.7C1C—C2C—C4C119.92 (17)
C11A—C12A—H16109.7C1C—C2C—C3C118.50 (19)
H15—C12A—H16108.2C4C—C2C—C3C121.57 (18)
N2A—C11A—C12A110.52 (18)N1C—C1C—C2C123.68 (18)
N2A—C11A—H17109.5N1C—C1C—H60118.2
C12A—C11A—H17109.5C2C—C1C—H60118.2
N2A—C11A—H9109.5N1C—C10C—C5C119.11 (16)
C12A—C11A—H9109.5N1C—C10C—C9C120.95 (16)
H17—C11A—H9108.1C5C—C10C—C9C119.92 (17)
C9A—C8A—N2A122.67 (17)C8C—C9C—C10C122.00 (17)
C9A—C8A—C7A115.76 (17)C8C—C9C—H53119.0
N2A—C8A—C7A121.45 (17)C10C—C9C—H53119.0
C8A—C9A—C10A121.86 (17)C9C—C8C—N2C123.98 (17)
C8A—C9A—H19119.1C9C—C8C—C7C115.96 (17)
C10A—C9A—H19119.1N2C—C8C—C7C119.95 (17)
C5A—C10A—N1A119.08 (16)N2C—C11C—C12C111.32 (16)
C5A—C10A—C9A120.57 (17)N2C—C11C—H45109.4
N1A—C10A—C9A120.34 (17)C12C—C11C—H45109.4
C10A—C5A—C6A117.94 (17)N2C—C11C—H46109.4
C10A—C5A—C4A121.39 (17)C12C—C11C—H46109.4
C6A—C5A—C4A120.65 (17)H45—C11C—H46108.0
O3A—C4A—C2A122.96 (18)N3C—C12C—C11C110.67 (17)
O3A—C4A—C5A121.30 (18)N3C—C12C—H47109.5
C2A—C4A—C5A115.74 (17)C11C—C12C—H47109.5
C1A—C2A—C4A120.08 (18)N3C—C12C—H48109.5
C1A—C2A—C3A117.98 (19)C11C—C12C—H48109.5
C4A—C2A—C3A121.94 (19)H47—C12C—H48108.1
O1A—C3A—O2A121.4 (2)C6C—C5C—C10C118.40 (17)
O1A—C3A—C2A123.6 (2)C6C—C5C—C4C120.83 (17)
O2A—C3A—C2A115.1 (2)C10C—C5C—C4C120.76 (17)
N1A—C15A—C16A111.6 (2)O3C—C4C—C2C122.69 (17)
N1A—C15A—H6109.3O3C—C4C—C5C120.71 (18)
C16A—C15A—H6109.3C2C—C4C—C5C116.59 (17)
N1A—C15A—H7109.3C7C—C6C—C5C120.05 (17)
C16A—C15A—H7109.3C7C—C6C—H54120.0
H6—C15A—H7108.0C5C—C6C—H54120.0
C15A—C16A—H4109.5C6C—C7C—F1C118.98 (17)
C15A—C16A—H3109.5C6C—C7C—C8C123.51 (18)
H4—C16A—H3109.5F1C—C7C—C8C117.48 (17)
C15A—C16A—H5109.5N2C—C14C—C13C113.52 (17)
H4—C16A—H5109.5N2C—C14C—H52108.9
H3—C16A—H5109.5C13C—C14C—H52108.9
N1A—C1A—C2A124.28 (19)N2C—C14C—H51108.9
N1A—C1A—H8117.9C13C—C14C—H51108.9
C2A—C1A—H8117.9H52—C14C—H51107.7
N3A—C13A—C14A112.47 (18)N3C—C13C—C14C109.75 (16)
N3A—C13A—H14109.1N3C—C13C—H49109.7
C14A—C13A—H14109.1C14C—C13C—H49109.7
N3A—C13A—H13109.1N3C—C13C—H50109.7
C14A—C13A—H13109.1C14C—C13C—H50109.7
H14—C13A—H13107.8H49—C13C—H50108.2
N2A—C14A—C13A111.54 (16)N1C—C15C—C16C111.93 (17)
N2A—C14A—H12109.3N1C—C15C—H58109.2
C13A—C14A—H12109.3C16C—C15C—H58109.2
N2A—C14A—H11109.3N1C—C15C—H59109.2
C13A—C14A—H11109.3C16C—C15C—H59109.2
H12—C14A—H11108.0H58—C15C—H59107.9
C6A—C7A—F1A117.47 (17)C15C—C16C—H57109.5
C6A—C7A—C8A123.24 (18)C15C—C16C—H55109.5
F1A—C7A—C8A119.24 (17)H57—C16C—H55109.5
C7A—C6A—C5A120.58 (18)C15C—C16C—H56109.5
C7A—C6A—H18119.7H57—C16C—H56109.5
C5A—C6A—H18119.7H55—C16C—H56109.5
O1B—C3B—O2B121.8 (2)O2Y—C7Y—O1Y122.51 (19)
O1B—C3B—C2B124.1 (2)O2Y—C7Y—C1Y119.06 (18)
O2B—C3B—C2B114.1 (2)O1Y—C7Y—C1Y118.40 (18)
C1B—C2B—C4B119.93 (18)C6Y—C1Y—C2Y117.90 (17)
C1B—C2B—C3B118.8 (2)C6Y—C1Y—C7Y120.85 (17)
C4B—C2B—C3B121.28 (19)C2Y—C1Y—C7Y121.24 (18)
O3B—C4B—C2B123.01 (18)C5Y—C6Y—C1Y121.41 (18)
O3B—C4B—C5B121.09 (19)C5Y—C6Y—H62119.3
C2B—C4B—C5B115.90 (17)C1Y—C6Y—H62119.3
C10B—C5B—C6B118.14 (17)C6Y—C5Y—C4Y119.98 (18)
C10B—C5B—C4B121.66 (18)C6Y—C5Y—H63120.0
C6B—C5B—C4B120.20 (17)C4Y—C5Y—H63120.0
C7B—C6B—C5B120.37 (18)O3Y—C4Y—C3Y118.34 (17)
C7B—C6B—H29119.8O3Y—C4Y—C5Y122.47 (18)
C5B—C6B—H29119.8C3Y—C4Y—C5Y119.19 (18)
C6B—C7B—F1B118.72 (17)C3Y—C2Y—C1Y121.44 (18)
C6B—C7B—C8B123.28 (19)C3Y—C2Y—H65119.3
F1B—C7B—C8B117.98 (18)C1Y—C2Y—H65119.3
C9B—C8B—N2B124.24 (17)C2Y—C3Y—C4Y120.06 (18)
C9B—C8B—C7B116.31 (17)C2Y—C3Y—H64120.0
N2B—C8B—C7B119.39 (17)C4Y—C3Y—H64120.0
N2B—C11B—C12B111.72 (16)O2Z—C7Z—O1Z123.31 (18)
N2B—C11B—H35109.3O2Z—C7Z—C1Z118.54 (19)
C12B—C11B—H35109.3O1Z—C7Z—C1Z118.10 (18)
N2B—C11B—H34109.3C2Z—C1Z—C6Z117.91 (17)
C12B—C11B—H34109.3C2Z—C1Z—C7Z121.39 (18)
H35—C11B—H34107.9C6Z—C1Z—C7Z120.68 (17)
N3B—C12B—C11B110.03 (18)C3Z—C2Z—C1Z121.63 (19)
N3B—C12B—H36109.7C3Z—C2Z—H69119.2
C11B—C12B—H36109.7C1Z—C2Z—H69119.2
N3B—C12B—H21109.7C2Z—C3Z—C4Z119.49 (18)
C11B—C12B—H21109.7C2Z—C3Z—H70120.3
H36—C12B—H21108.2C4Z—C3Z—H70120.3
N1B—C10B—C5B118.62 (16)O3Z—C4Z—C3Z117.93 (18)
N1B—C10B—C9B121.28 (17)O3Z—C4Z—C5Z122.10 (18)
C5B—C10B—C9B120.09 (17)C3Z—C4Z—C5Z119.96 (18)
N1B—C1B—C2B124.05 (19)C5Z—C6Z—C1Z121.02 (18)
N1B—C1B—H22118.0C5Z—C6Z—H67119.5
C2B—C1B—H22118.0C1Z—C6Z—H67119.5
N1B—C15B—C16B110.99 (18)C6Z—C5Z—C4Z119.98 (18)
N1B—C15B—H26109.4C6Z—C5Z—H68120.0
C16B—C15B—H26109.4C4Z—C5Z—H68120.0
C13A—N3A—C12A—C11A56.6 (2)C8B—N2B—C14B—C13B91.2 (2)
C8A—N2A—C11A—C12A163.13 (18)C11B—N2B—C14B—C13B53.2 (2)
C14A—N2A—C11A—C12A59.6 (2)C12B—N3B—C13B—C14B57.3 (2)
N3A—C12A—C11A—N2A60.5 (2)N2B—C14B—C13B—N3B54.7 (2)
C11A—N2A—C8A—C9A134.2 (2)O2X—C7X—C1X—C6X168.34 (18)
C14A—N2A—C8A—C9A0.3 (3)O1X—C7X—C1X—C6X14.0 (3)
C11A—N2A—C8A—C7A50.0 (3)O2X—C7X—C1X—C2X12.7 (3)
C14A—N2A—C8A—C7A175.53 (19)O1X—C7X—C1X—C2X165.03 (18)
N2A—C8A—C9A—C10A174.86 (18)C6X—C1X—C2X—C3X1.6 (3)
C7A—C8A—C9A—C10A1.2 (3)C7X—C1X—C2X—C3X177.45 (18)
C1A—N1A—C10A—C5A0.3 (3)C1X—C2X—C3X—C4X0.9 (3)
C15A—N1A—C10A—C5A176.6 (2)C2X—C3X—C4X—O3X178.67 (18)
C1A—N1A—C10A—C9A179.07 (19)C2X—C3X—C4X—C5X0.6 (3)
C15A—N1A—C10A—C9A4.0 (3)O3X—C4X—C5X—C6X177.95 (18)
C8A—C9A—C10A—C5A2.4 (3)C3X—C4X—C5X—C6X1.3 (3)
C8A—C9A—C10A—N1A176.96 (18)C4X—C5X—C6X—C1X0.5 (3)
N1A—C10A—C5A—C6A177.97 (18)C2X—C1X—C6X—C5X0.9 (3)
C9A—C10A—C5A—C6A1.4 (3)C7X—C1X—C6X—C5X178.14 (18)
N1A—C10A—C5A—C4A0.2 (3)O1C—C3C—C2C—C1C0.8 (3)
C9A—C10A—C5A—C4A179.52 (18)O2C—C3C—C2C—C1C179.46 (18)
C10A—C5A—C4A—O3A179.8 (2)O1C—C3C—C2C—C4C179.1 (2)
C6A—C5A—C4A—O3A2.1 (3)O2C—C3C—C2C—C4C0.6 (3)
C10A—C5A—C4A—C2A1.2 (3)C10C—N1C—C1C—C2C2.1 (3)
C6A—C5A—C4A—C2A176.87 (19)C15C—N1C—C1C—C2C178.95 (18)
O3A—C4A—C2A—C1A179.2 (2)C4C—C2C—C1C—N1C0.4 (3)
C5A—C4A—C2A—C1A1.9 (3)C3C—C2C—C1C—N1C179.67 (19)
O3A—C4A—C2A—C3A1.7 (3)C1C—N1C—C10C—C5C2.1 (3)
C5A—C4A—C2A—C3A177.22 (19)C15C—N1C—C10C—C5C178.74 (18)
C1A—C2A—C3A—O1A2.6 (4)C1C—N1C—C10C—C9C176.77 (18)
C4A—C2A—C3A—O1A176.6 (2)C15C—N1C—C10C—C9C0.1 (3)
C1A—C2A—C3A—O2A178.1 (2)N1C—C10C—C9C—C8C177.52 (17)
C4A—C2A—C3A—O2A2.8 (3)C5C—C10C—C9C—C8C1.3 (3)
C1A—N1A—C15A—C16A96.5 (2)C10C—C9C—C8C—N2C179.93 (18)
C10A—N1A—C15A—C16A80.4 (3)C10C—C9C—C8C—C7C3.9 (3)
C10A—N1A—C1A—C2A0.4 (3)C14C—N2C—C8C—C9C10.7 (3)
C15A—N1A—C1A—C2A177.5 (2)C11C—N2C—C8C—C9C128.5 (2)
C4A—C2A—C1A—N1A1.6 (3)C14C—N2C—C8C—C7C165.28 (18)
C3A—C2A—C1A—N1A177.6 (2)C11C—N2C—C8C—C7C55.5 (3)
C12A—N3A—C13A—C14A53.4 (2)C8C—N2C—C11C—C12C86.9 (2)
C8A—N2A—C14A—C13A166.66 (17)C14C—N2C—C11C—C12C55.8 (2)
C11A—N2A—C14A—C13A55.5 (2)C13C—N3C—C12C—C11C56.7 (2)
N3A—C13A—C14A—N2A53.2 (2)N2C—C11C—C12C—N3C57.3 (2)
C9A—C8A—C7A—C6A1.0 (3)N1C—C10C—C5C—C6C179.49 (17)
N2A—C8A—C7A—C6A177.06 (19)C9C—C10C—C5C—C6C1.7 (3)
C9A—C8A—C7A—F1A176.37 (18)N1C—C10C—C5C—C4C0.3 (3)
N2A—C8A—C7A—F1A0.3 (3)C9C—C10C—C5C—C4C178.53 (18)
F1A—C7A—C6A—C5A175.44 (18)C1C—C2C—C4C—O3C178.71 (19)
C8A—C7A—C6A—C5A1.9 (3)C3C—C2C—C4C—O3C1.3 (3)
C10A—C5A—C6A—C7A0.7 (3)C1C—C2C—C4C—C5C1.4 (3)
C4A—C5A—C6A—C7A177.45 (19)C3C—C2C—C4C—C5C178.60 (18)
O1B—C3B—C2B—C1B1.6 (4)C6C—C5C—C4C—O3C1.1 (3)
O2B—C3B—C2B—C1B179.0 (2)C10C—C5C—C4C—O3C178.70 (18)
O1B—C3B—C2B—C4B178.1 (2)C6C—C5C—C4C—C2C178.85 (18)
O2B—C3B—C2B—C4B1.3 (3)C10C—C5C—C4C—C2C1.4 (3)
C1B—C2B—C4B—O3B179.5 (2)C10C—C5C—C6C—C7C1.7 (3)
C3B—C2B—C4B—O3B0.9 (3)C4C—C5C—C6C—C7C178.46 (19)
C1B—C2B—C4B—C5B0.3 (3)C5C—C6C—C7C—F1C176.88 (18)
C3B—C2B—C4B—C5B179.39 (19)C5C—C6C—C7C—C8C1.1 (3)
O3B—C4B—C5B—C10B179.17 (19)C9C—C8C—C7C—C6C3.9 (3)
C2B—C4B—C5B—C10B0.6 (3)N2C—C8C—C7C—C6C179.76 (19)
O3B—C4B—C5B—C6B0.4 (3)C9C—C8C—C7C—F1C174.10 (17)
C2B—C4B—C5B—C6B179.83 (18)N2C—C8C—C7C—F1C2.2 (3)
C10B—C5B—C6B—C7B1.5 (3)C8C—N2C—C14C—C13C87.1 (2)
C4B—C5B—C6B—C7B178.9 (2)C11C—N2C—C14C—C13C55.4 (2)
C5B—C6B—C7B—F1B177.07 (18)C12C—N3C—C13C—C14C54.6 (2)
C5B—C6B—C7B—C8B1.1 (3)N2C—C14C—C13C—N3C54.7 (2)
C14B—N2B—C8B—C9B14.3 (3)C1C—N1C—C15C—C16C97.0 (2)
C11B—N2B—C8B—C9B127.6 (2)C10C—N1C—C15C—C16C79.7 (2)
C14B—N2B—C8B—C7B162.79 (18)O2Y—C7Y—C1Y—C6Y174.64 (18)
C11B—N2B—C8B—C7B55.3 (3)O1Y—C7Y—C1Y—C6Y7.2 (3)
C6B—C7B—C8B—C9B3.2 (3)O2Y—C7Y—C1Y—C2Y6.3 (3)
F1B—C7B—C8B—C9B175.00 (18)O1Y—C7Y—C1Y—C2Y171.87 (18)
C6B—C7B—C8B—N2B179.5 (2)C2Y—C1Y—C6Y—C5Y0.9 (3)
F1B—C7B—C8B—N2B2.3 (3)C7Y—C1Y—C6Y—C5Y178.25 (17)
C8B—N2B—C11B—C12B91.0 (2)C1Y—C6Y—C5Y—C4Y0.6 (3)
C14B—N2B—C11B—C12B53.7 (2)C6Y—C5Y—C4Y—O3Y179.85 (18)
C13B—N3B—C12B—C11B59.6 (2)C6Y—C5Y—C4Y—C3Y0.5 (3)
N2B—C11B—C12B—N3B57.2 (2)C6Y—C1Y—C2Y—C3Y1.1 (3)
C1B—N1B—C10B—C5B1.4 (3)C7Y—C1Y—C2Y—C3Y178.03 (18)
C15B—N1B—C10B—C5B176.48 (19)C1Y—C2Y—C3Y—C4Y1.0 (3)
C1B—N1B—C10B—C9B177.29 (19)O3Y—C4Y—C3Y—C2Y179.91 (18)
C15B—N1B—C10B—C9B2.2 (3)C5Y—C4Y—C3Y—C2Y0.7 (3)
C6B—C5B—C10B—N1B179.38 (17)O2Z—C7Z—C1Z—C2Z8.4 (3)
C4B—C5B—C10B—N1B0.2 (3)O1Z—C7Z—C1Z—C2Z169.21 (18)
C6B—C5B—C10B—C9B2.0 (3)O2Z—C7Z—C1Z—C6Z172.90 (18)
C4B—C5B—C10B—C9B178.46 (18)O1Z—C7Z—C1Z—C6Z9.5 (3)
C10B—N1B—C1B—C2B1.8 (3)C6Z—C1Z—C2Z—C3Z0.9 (3)
C15B—N1B—C1B—C2B177.1 (2)C7Z—C1Z—C2Z—C3Z177.87 (19)
C4B—C2B—C1B—N1B0.9 (3)C1Z—C2Z—C3Z—C4Z0.8 (3)
C3B—C2B—C1B—N1B179.42 (19)C2Z—C3Z—C4Z—O3Z179.33 (18)
C1B—N1B—C15B—C16B95.0 (2)C2Z—C3Z—C4Z—C5Z0.4 (3)
C10B—N1B—C15B—C16B80.2 (2)C2Z—C1Z—C6Z—C5Z0.5 (3)
N2B—C8B—C9B—C10B179.85 (18)C7Z—C1Z—C6Z—C5Z178.22 (18)
C7B—C8B—C9B—C10B2.7 (3)C1Z—C6Z—C5Z—C4Z0.2 (3)
N1B—C10B—C9B—C8B178.42 (17)O3Z—C4Z—C5Z—C6Z178.97 (18)
C5B—C10B—C9B—C8B0.2 (3)C3Z—C4Z—C5Z—C6Z0.1 (3)

Experimental details

(20120152_0m)(20120156_0m)(20120175_0m)(2013130_0m)
Crystal data
Chemical formulaC44H56F2N6O14C41H57F2N6O21C23H26FN3O7C21H30FN3O10S
Mr930.951007.93475.47535.55
Crystal system, space groupTriclinic, P1Triclinic, P1Monoclinic, P21/cTriclinic, P1
Temperature (K)100100100100
a, b, c (Å)9.4994 (3), 14.3694 (4), 18.1458 (5)7.4031 (3), 9.7515 (3), 30.9801 (10)8.0761 (2), 14.7184 (3), 18.7770 (4)9.041 (3), 10.767 (3), 12.438 (3)
α, β, γ (°)103.853 (1), 96.528 (1), 106.946 (2)88.088 (2), 85.673 (2), 81.380 (2)90, 99.269 (1), 9089.118 (19), 81.880 (17), 74.64 (2)
V3)2255.11 (11)2204.38 (13)2202.83 (8)1155.6 (5)
Z2242
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.110.130.110.21
Crystal size (mm)0.31 × 0.23 × 0.150.21 × 0.08 × 0.050.42 × 0.32 × 0.210.21 × 0.15 × 0.13
Data collection
DiffractometerCCD area detector
diffractometer
CCD area detector
diffractometer
CCD area detector
diffractometer
CCD area detector
diffractometer
Absorption correction
Tmin, Tmax
No. of measured, independent and
observed [I > 2σ(I)] reflections
31371, 7942, 5556 31596, 7784, 4274 31912, 3883, 3253 15891, 4065, 2459
Rint0.0300.0590.0340.101
(sin θ/λ)max1)0.5950.5950.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.132, 0.99 0.052, 0.131, 1.00 0.033, 0.086, 1.05 0.047, 0.075, 1.08
No. of reflections7942778438834065
No. of parameters633673328334
No. of restraints16414022
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.68, 0.190.41, 0.310.21, 0.250.41, 0.41


(2013176_0ma)(2013329_0m)(mo_2014070_0m)
Crystal data
Chemical formulaC26H23FN3O10SC23H26FN3O7C23H26FN3O7
Mr588.54475.47475.47
Crystal system, space groupOrthorhombic, PbcaTriclinic, P1Triclinic, P1
Temperature (K)100296296
a, b, c (Å)11.6515 (3), 7.4209 (2), 61.8325 (18)7.0237 (4), 9.9645 (5), 17.4655 (9)7.3258 (2), 19.8297 (4), 23.9108 (5)
α, β, γ (°)90, 90, 9091.100 (3), 97.543 (3), 109.906 (3)96.924 (1), 97.210 (1), 96.143 (1)
V3)5346.3 (3)1136.71 (10)3394.48 (14)
Z826
Radiation typeMo KαMo KαMo Kα
µ (mm1)0.190.110.11
Crystal size (mm)0.30 × 0.04 × 0.030.15 × 0.06 × 0.030.60 × 0.15 × 0.08
Data collection
DiffractometerCCD area detector
diffractometer
CCD area detector
diffractometer
CCD area detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
SADABS
Empirical (using intensity measurements)
SADABS
Empirical (using intensity measurements)
SADABS
Tmin, Tmax0.948, 0.9950.984, 0.9970.938, 0.991
No. of measured, independent and
observed [I > 2σ(I)] reflections
47387, 5987, 3739 17531, 5221, 2989 49327, 15579, 7689
Rint0.1030.0290.047
(sin θ/λ)max1)0.6500.6500.651
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.068, 0.164, 1.12 0.044, 0.112, 1.00 0.049, 0.122, 0.95
No. of reflections5987522115579
No. of parameters419322972
No. of restraints403
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.43, 0.400.17, 0.200.18, 0.19

Computer programs: Bruker SMART, SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

 

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