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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
CCDC references: 1004351; 1004352; 1004353; 1004354; 1004355; 1004356; 1004357
Crystal data, data collection and structure refinement details are summarized
in Table 1.
S2. Results and discussion
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).
Crystal data top
C44H56F2N6O14 | V = 2255.11 (11) Å3 |
Mr = 930.95 | Z = 2 |
Triclinic, P1 | F(000) = 984.0 |
a = 9.4994 (3) Å | Dx = 1.371 Mg m−3 |
b = 14.3694 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 18.1458 (5) Å | µ = 0.11 mm−1 |
α = 103.853 (1)° | T = 100 K |
β = 96.528 (1)° | Block, colorless |
γ = 106.946 (2)° | 0.31 × 0.23 × 0.15 mm |
Data collection top
CCD area detector diffractometer | 5556 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
phi and ω scans | h = −11→11 |
31371 measured reflections | k = −17→17 |
7942 independent reflections | l = −20→21 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H 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 parameters | Δρmax = 0.68 e Å−3 |
164 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C44H56F2N6O14 | γ = 106.946 (2)° |
Mr = 930.95 | V = 2255.11 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.4994 (3) Å | Mo Kα radiation |
b = 14.3694 (4) Å | µ = 0.11 mm−1 |
c = 18.1458 (5) Å | T = 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 reflections | Rint = 0.030 |
7942 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.045 | 164 restraints |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.99 | Δρmax = 0.68 e Å−3 |
7942 reflections | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O3Y | 0.09506 (16) | 0.71691 (11) | 0.55069 (8) | 0.0386 (4) | |
O1Y | 0.40092 (16) | 0.29493 (11) | 0.47177 (9) | 0.0405 (4) | |
O4X | 0.55392 (17) | 0.17700 (11) | 0.45828 (9) | 0.0400 (4) | |
H10' | 0.495 (3) | 0.219 (2) | 0.4646 (15) | 0.060* | |
O3X | 0.5423 (2) | 0.18818 (15) | 0.58111 (10) | 0.0655 (5) | |
O1X | 0.9071 (2) | −0.18355 (14) | 0.68179 (10) | 0.0589 (5) | |
O1A | −0.3670 (2) | 0.86399 (16) | 1.12710 (11) | 0.0738 (6) | |
O2A | −0.1405 (2) | 0.94601 (15) | 1.19827 (10) | 0.0608 (5) | |
O3A | 0.0877 (2) | 0.96134 (14) | 1.13573 (9) | 0.0566 (5) | |
F1A | 0.41171 (15) | 0.91658 (12) | 0.93795 (8) | 0.0671 (5) | |
N3A | 0.3352 (2) | 0.73711 (14) | 0.66485 (10) | 0.0348 (4) | |
O2B | 1.1294 (3) | 0.54982 (18) | −0.15755 (12) | 0.0879 (7) | |
H28 | 1.0436 | 0.5345 | −0.1495 | 0.132* | |
O1B | 1.3554 (3) | 0.6509 (2) | −0.09273 (14) | 0.1025 (8) | |
O3B | 0.9041 (3) | 0.53883 (15) | −0.09410 (10) | 0.0733 (6) | |
F1B | 0.58306 (16) | 0.58257 (12) | 0.10412 (8) | 0.0650 (4) | |
N3B | 0.7313 (2) | 0.69798 (15) | 0.39929 (11) | 0.0382 (4) | |
O4Y | −0.03338 (19) | 0.63743 (14) | 0.43068 (9) | 0.0574 (5) | |
N2A | 0.22813 (19) | 0.80111 (13) | 0.80036 (10) | 0.0381 (4) | |
N1A | −0.1982 (2) | 0.80455 (15) | 0.92662 (10) | 0.0445 (5) | |
C5A | 0.0559 (2) | 0.88715 (16) | 1.00071 (12) | 0.0361 (5) | |
N2B | 0.76965 (19) | 0.69207 (13) | 0.24427 (10) | 0.0367 (4) | |
C1Y | 0.3975 (2) | 0.35251 (15) | 0.42878 (12) | 0.0315 (5) | |
O2Y | 0.47495 (18) | 0.36090 (13) | 0.37836 (9) | 0.0487 (4) | |
C1X | 0.9029 (2) | −0.13542 (16) | 0.63617 (13) | 0.0375 (5) | |
C2X | 0.8266 (3) | −0.05630 (17) | 0.64539 (13) | 0.0411 (5) | |
H3' | 0.8842 | 0.0001 | 0.6901 | 0.049* | |
H2' | 0.7286 | −0.0852 | 0.6568 | 0.049* | |
C3X | 0.8053 (2) | −0.01472 (16) | 0.57773 (13) | 0.0378 (5) | |
H5' | 0.7516 | −0.0707 | 0.5320 | 0.045* | |
H4' | 0.9030 | 0.0189 | 0.5681 | 0.045* | |
C4X | 0.7192 (2) | 0.06014 (16) | 0.59084 (13) | 0.0373 (5) | |
H7' | 0.6245 | 0.0284 | 0.6043 | 0.045* | |
H6' | 0.7766 | 0.1189 | 0.6339 | 0.045* | |
C5X | 0.6891 (2) | 0.09420 (17) | 0.51948 (14) | 0.0414 (5) | |
H9' | 0.7844 | 0.1324 | 0.5100 | 0.050* | |
H8' | 0.6440 | 0.0344 | 0.4754 | 0.050* | |
C6X | 0.5890 (2) | 0.15817 (15) | 0.52413 (13) | 0.0357 (5) | |
C13A | 0.2463 (2) | 0.66372 (16) | 0.70165 (12) | 0.0359 (5) | |
H17 | 0.3131 | 0.6505 | 0.7393 | 0.043* | |
H16 | 0.1908 | 0.6000 | 0.6626 | 0.043* | |
C14A | 0.1389 (2) | 0.70741 (16) | 0.74096 (12) | 0.0348 (5) | |
H18 | 0.0722 | 0.7213 | 0.7037 | 0.042* | |
H19 | 0.0786 | 0.6597 | 0.7642 | 0.042* | |
C8A | 0.1659 (2) | 0.83386 (16) | 0.86427 (12) | 0.0365 (5) | |
C9A | 0.0135 (2) | 0.80628 (17) | 0.86212 (12) | 0.0385 (5) | |
H3 | −0.0528 | 0.7701 | 0.8153 | 0.046* | |
C10A | −0.0433 (2) | 0.83194 (16) | 0.92947 (12) | 0.0367 (5) | |
C1A | −0.2492 (3) | 0.82580 (19) | 0.99254 (13) | 0.0468 (6) | |
H1 | −0.3525 | 0.8054 | 0.9894 | 0.056* | |
C2A | −0.1595 (3) | 0.87527 (17) | 1.06383 (13) | 0.0409 (5) | |
C3A | −0.2331 (3) | 0.89331 (19) | 1.13152 (14) | 0.0491 (6) | |
C15A | −0.3073 (3) | 0.7540 (2) | 0.85188 (14) | 0.0598 (7) | |
H5 | −0.2676 | 0.7827 | 0.8123 | 0.072* | |
H4 | −0.4003 | 0.7678 | 0.8571 | 0.072* | |
C16A | −0.3395 (3) | 0.6422 (2) | 0.82674 (17) | 0.0749 (9) | |
H8 | −0.2470 | 0.6280 | 0.8253 | 0.112* | |
H7 | −0.4023 | 0.6140 | 0.7761 | 0.112* | |
H6 | −0.3900 | 0.6124 | 0.8626 | 0.112* | |
C4A | −0.0005 (3) | 0.91138 (16) | 1.07162 (12) | 0.0392 (5) | |
C6A | 0.2109 (3) | 0.91721 (17) | 1.00194 (13) | 0.0426 (5) | |
H2 | 0.2784 | 0.9549 | 1.0481 | 0.051* | |
C7A | 0.2621 (2) | 0.89129 (17) | 0.93584 (13) | 0.0422 (5) | |
C11A | 0.3110 (2) | 0.87789 (16) | 0.76618 (13) | 0.0407 (5) | |
H10 | 0.3678 | 0.9398 | 0.8068 | 0.049* | |
H11 | 0.2412 | 0.8935 | 0.7317 | 0.049* | |
C12A | 0.4164 (2) | 0.83817 (17) | 0.72167 (13) | 0.0416 (5) | |
H13 | 0.4630 | 0.8858 | 0.6945 | 0.050* | |
H12 | 0.4952 | 0.8324 | 0.7575 | 0.050* | |
C13B | 0.7843 (3) | 0.79221 (17) | 0.37611 (13) | 0.0430 (5) | |
H36 | 0.8504 | 0.8468 | 0.4199 | 0.052* | |
H35 | 0.6994 | 0.8119 | 0.3595 | 0.052* | |
C14B | 0.8677 (2) | 0.77425 (17) | 0.31048 (12) | 0.0401 (5) | |
H37 | 0.9027 | 0.8359 | 0.2951 | 0.048* | |
H38 | 0.9546 | 0.7569 | 0.3279 | 0.048* | |
C8B | 0.8290 (2) | 0.67663 (16) | 0.17582 (12) | 0.0362 (5) | |
C7B | 0.7320 (3) | 0.61764 (18) | 0.10489 (13) | 0.0441 (5) | |
C6B | 0.7821 (3) | 0.59406 (18) | 0.03778 (13) | 0.0486 (6) | |
H21 | 0.7142 | 0.5538 | −0.0077 | 0.058* | |
C5B | 0.9356 (3) | 0.63027 (17) | 0.03707 (13) | 0.0443 (5) | |
C4B | 0.9926 (3) | 0.59992 (19) | −0.03296 (14) | 0.0538 (6) | |
C2B | 1.1498 (4) | 0.6410 (2) | −0.02720 (15) | 0.0581 (7) | |
C3B | 1.2223 (5) | 0.6152 (3) | −0.09452 (19) | 0.0739 (9) | |
C11B | 0.7143 (3) | 0.59792 (17) | 0.26671 (13) | 0.0420 (5) | |
H30 | 0.7983 | 0.5767 | 0.2822 | 0.050* | |
H29 | 0.6472 | 0.5445 | 0.2226 | 0.050* | |
C12B | 0.6321 (2) | 0.61347 (18) | 0.33270 (13) | 0.0436 (5) | |
H31 | 0.5430 | 0.6289 | 0.3160 | 0.052* | |
H32 | 0.6007 | 0.5517 | 0.3482 | 0.052* | |
C9B | 0.9790 (2) | 0.71591 (17) | 0.17440 (13) | 0.0395 (5) | |
H22 | 1.0455 | 0.7583 | 0.2198 | 0.047* | |
C10B | 1.0339 (3) | 0.69334 (17) | 0.10583 (13) | 0.0423 (5) | |
N1B | 1.1872 (2) | 0.73114 (17) | 0.10611 (12) | 0.0537 (5) | |
C1B | 1.2380 (3) | 0.7033 (2) | 0.04093 (16) | 0.0611 (7) | |
H20 | 1.3407 | 0.7287 | 0.0428 | 0.073* | |
C15B | 1.2969 (3) | 0.7930 (3) | 0.17795 (19) | 0.0781 (9) | |
C16B | 1.3397 (5) | 0.7303 (4) | 0.2236 (2) | 0.1274 (17) | |
H25 | 1.2511 | 0.6864 | 0.2338 | 0.191* | |
H27 | 1.4044 | 0.7735 | 0.2717 | 0.191* | |
H26 | 1.3914 | 0.6901 | 0.1951 | 0.191* | |
C6Y | 0.0700 (2) | 0.65237 (15) | 0.48522 (12) | 0.0325 (5) | |
C5Y | 0.1726 (2) | 0.58944 (16) | 0.47490 (13) | 0.0381 (5) | |
H18' | 0.2755 | 0.6353 | 0.4899 | 0.046* | |
H17' | 0.1587 | 0.5484 | 0.5105 | 0.046* | |
C4Y | 0.1533 (3) | 0.5205 (2) | 0.39554 (13) | 0.0502 (6) | |
H16' | 0.1510 | 0.5587 | 0.3582 | 0.060* | |
H15' | 0.0574 | 0.4666 | 0.3836 | 0.060* | |
C3Y | 0.2769 (3) | 0.4734 (2) | 0.38662 (14) | 0.0495 (6) | |
H13' | 0.2566 | 0.4296 | 0.3341 | 0.059* | |
H14' | 0.3717 | 0.5271 | 0.3943 | 0.059* | |
C2Y | 0.2920 (2) | 0.41288 (16) | 0.44189 (13) | 0.0363 (5) | |
H11' | 0.1932 | 0.3663 | 0.4395 | 0.044* | |
H12' | 0.3256 | 0.4590 | 0.4939 | 0.044* | |
H14 | 0.404 (2) | 0.7100 (18) | 0.6451 (14) | 0.057 (7)* | |
H33 | 0.683 (2) | 0.7060 (17) | 0.4396 (11) | 0.047 (7)* | |
H15 | 0.270 (2) | 0.7407 (17) | 0.6252 (11) | 0.050 (7)* | |
H23 | 1.267 (3) | 0.856 (2) | 0.2092 (19) | 0.089 (10)* | |
H9 | −0.048 (4) | 0.961 (3) | 1.186 (2) | 0.102 (13)* | |
O2X | 0.96215 (19) | −0.14786 (13) | 0.57354 (10) | 0.0499 (4) | |
H24 | 1.383 (4) | 0.843 (3) | 0.161 (2) | 0.106 (11)* | |
H34 | 0.811 (2) | 0.6789 (18) | 0.4155 (14) | 0.058 (7)* | |
H1' | 1.006 (3) | −0.201 (2) | 0.5678 (18) | 0.086 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O3Y | 0.0398 (8) | 0.0422 (8) | 0.0398 (8) | 0.0243 (7) | 0.0104 (7) | 0.0083 (7) |
O1Y | 0.0471 (9) | 0.0490 (9) | 0.0448 (9) | 0.0315 (7) | 0.0214 (7) | 0.0235 (8) |
O4X | 0.0442 (9) | 0.0461 (9) | 0.0451 (9) | 0.0275 (7) | 0.0179 (7) | 0.0211 (7) |
O3X | 0.0963 (14) | 0.0898 (14) | 0.0465 (10) | 0.0696 (12) | 0.0314 (10) | 0.0292 (10) |
O1X | 0.0848 (13) | 0.0687 (12) | 0.0478 (10) | 0.0512 (10) | 0.0165 (9) | 0.0278 (9) |
O1A | 0.0676 (12) | 0.0929 (15) | 0.0615 (12) | 0.0251 (11) | 0.0404 (10) | 0.0122 (11) |
O2A | 0.0787 (13) | 0.0746 (13) | 0.0375 (10) | 0.0355 (11) | 0.0274 (10) | 0.0112 (9) |
O3A | 0.0649 (11) | 0.0677 (11) | 0.0320 (9) | 0.0231 (9) | 0.0137 (8) | 0.0015 (8) |
F1A | 0.0380 (7) | 0.0846 (11) | 0.0528 (9) | 0.0027 (7) | 0.0143 (7) | −0.0083 (8) |
N3A | 0.0361 (10) | 0.0476 (11) | 0.0316 (10) | 0.0252 (8) | 0.0144 (8) | 0.0138 (8) |
O2B | 0.168 (2) | 0.0890 (16) | 0.0523 (12) | 0.0826 (16) | 0.0615 (14) | 0.0359 (11) |
O1B | 0.134 (2) | 0.134 (2) | 0.0920 (17) | 0.0791 (17) | 0.0860 (16) | 0.0548 (16) |
O3B | 0.1195 (17) | 0.0771 (13) | 0.0344 (10) | 0.0504 (12) | 0.0222 (11) | 0.0108 (9) |
F1B | 0.0489 (8) | 0.0864 (11) | 0.0452 (8) | 0.0089 (8) | 0.0041 (7) | 0.0111 (8) |
N3B | 0.0390 (10) | 0.0569 (12) | 0.0326 (10) | 0.0266 (9) | 0.0179 (9) | 0.0197 (9) |
O4Y | 0.0564 (10) | 0.0862 (13) | 0.0416 (9) | 0.0512 (10) | 0.0032 (8) | 0.0090 (9) |
N2A | 0.0417 (10) | 0.0391 (10) | 0.0329 (10) | 0.0117 (8) | 0.0181 (8) | 0.0062 (8) |
N1A | 0.0407 (10) | 0.0651 (13) | 0.0324 (10) | 0.0230 (9) | 0.0135 (8) | 0.0129 (9) |
C5A | 0.0462 (12) | 0.0357 (11) | 0.0316 (11) | 0.0174 (9) | 0.0146 (9) | 0.0111 (9) |
N2B | 0.0409 (10) | 0.0400 (10) | 0.0293 (9) | 0.0112 (8) | 0.0119 (8) | 0.0108 (8) |
C1Y | 0.0311 (10) | 0.0328 (11) | 0.0347 (11) | 0.0161 (9) | 0.0106 (9) | 0.0082 (9) |
O2Y | 0.0560 (10) | 0.0672 (11) | 0.0537 (10) | 0.0440 (9) | 0.0362 (8) | 0.0325 (9) |
C1X | 0.0367 (12) | 0.0401 (12) | 0.0377 (12) | 0.0178 (10) | 0.0030 (10) | 0.0105 (10) |
C2X | 0.0469 (13) | 0.0443 (13) | 0.0377 (12) | 0.0250 (11) | 0.0067 (10) | 0.0105 (10) |
C3X | 0.0346 (11) | 0.0386 (12) | 0.0452 (13) | 0.0179 (9) | 0.0091 (10) | 0.0137 (10) |
C4X | 0.0371 (11) | 0.0360 (11) | 0.0414 (12) | 0.0175 (9) | 0.0064 (10) | 0.0097 (10) |
C5X | 0.0430 (12) | 0.0432 (13) | 0.0528 (14) | 0.0243 (10) | 0.0194 (11) | 0.0234 (11) |
C6X | 0.0386 (12) | 0.0340 (11) | 0.0419 (12) | 0.0160 (9) | 0.0141 (10) | 0.0163 (10) |
C13A | 0.0412 (12) | 0.0393 (12) | 0.0341 (11) | 0.0202 (10) | 0.0121 (10) | 0.0122 (9) |
C14A | 0.0367 (11) | 0.0385 (11) | 0.0321 (11) | 0.0150 (9) | 0.0124 (9) | 0.0097 (9) |
C8A | 0.0437 (12) | 0.0377 (12) | 0.0316 (11) | 0.0152 (10) | 0.0157 (9) | 0.0102 (9) |
C9A | 0.0408 (11) | 0.0486 (13) | 0.0283 (11) | 0.0175 (10) | 0.0104 (9) | 0.0098 (10) |
C10A | 0.0397 (11) | 0.0451 (12) | 0.0320 (11) | 0.0193 (10) | 0.0139 (9) | 0.0138 (10) |
C1A | 0.0467 (13) | 0.0605 (15) | 0.0437 (13) | 0.0257 (12) | 0.0229 (11) | 0.0176 (12) |
C2A | 0.0549 (13) | 0.0445 (13) | 0.0351 (11) | 0.0259 (11) | 0.0210 (10) | 0.0156 (10) |
C3A | 0.0654 (16) | 0.0524 (15) | 0.0434 (14) | 0.0296 (13) | 0.0290 (12) | 0.0179 (12) |
C15A | 0.0427 (13) | 0.099 (2) | 0.0430 (14) | 0.0317 (14) | 0.0127 (11) | 0.0186 (14) |
C16A | 0.0550 (17) | 0.098 (2) | 0.0539 (17) | 0.0156 (16) | 0.0081 (14) | 0.0023 (16) |
C4A | 0.0553 (13) | 0.0391 (12) | 0.0317 (11) | 0.0234 (10) | 0.0161 (10) | 0.0122 (10) |
C6A | 0.0460 (12) | 0.0427 (13) | 0.0319 (12) | 0.0111 (10) | 0.0082 (10) | 0.0020 (10) |
C7A | 0.0362 (11) | 0.0450 (13) | 0.0404 (12) | 0.0103 (10) | 0.0138 (10) | 0.0040 (10) |
C11A | 0.0447 (13) | 0.0387 (12) | 0.0413 (13) | 0.0135 (10) | 0.0206 (10) | 0.0109 (10) |
C12A | 0.0381 (12) | 0.0486 (13) | 0.0390 (12) | 0.0139 (10) | 0.0150 (10) | 0.0115 (10) |
C13B | 0.0487 (13) | 0.0466 (13) | 0.0380 (12) | 0.0192 (11) | 0.0166 (11) | 0.0118 (10) |
C14B | 0.0439 (12) | 0.0412 (12) | 0.0344 (12) | 0.0107 (10) | 0.0153 (10) | 0.0100 (10) |
C8B | 0.0462 (12) | 0.0395 (12) | 0.0291 (10) | 0.0182 (10) | 0.0139 (9) | 0.0130 (9) |
C7B | 0.0464 (13) | 0.0494 (14) | 0.0360 (12) | 0.0139 (11) | 0.0081 (10) | 0.0139 (11) |
C6B | 0.0698 (15) | 0.0480 (14) | 0.0281 (11) | 0.0206 (12) | 0.0076 (11) | 0.0106 (10) |
C5B | 0.0694 (15) | 0.0468 (13) | 0.0316 (11) | 0.0316 (12) | 0.0205 (11) | 0.0184 (10) |
C4B | 0.1001 (18) | 0.0531 (15) | 0.0330 (13) | 0.0476 (14) | 0.0274 (13) | 0.0232 (11) |
C2B | 0.0940 (18) | 0.0654 (17) | 0.0479 (14) | 0.0512 (15) | 0.0435 (14) | 0.0321 (13) |
C3B | 0.131 (3) | 0.081 (2) | 0.0607 (18) | 0.074 (2) | 0.0608 (19) | 0.0461 (16) |
C11B | 0.0470 (13) | 0.0407 (12) | 0.0365 (12) | 0.0089 (10) | 0.0135 (10) | 0.0122 (10) |
C12B | 0.0375 (12) | 0.0525 (14) | 0.0434 (13) | 0.0111 (10) | 0.0146 (10) | 0.0201 (11) |
C9B | 0.0453 (12) | 0.0443 (13) | 0.0308 (11) | 0.0155 (10) | 0.0142 (10) | 0.0103 (10) |
C10B | 0.0536 (13) | 0.0470 (13) | 0.0385 (12) | 0.0245 (11) | 0.0212 (10) | 0.0190 (10) |
N1B | 0.0564 (12) | 0.0713 (14) | 0.0447 (11) | 0.0272 (11) | 0.0292 (10) | 0.0207 (10) |
C1B | 0.0771 (18) | 0.0778 (19) | 0.0566 (15) | 0.0426 (15) | 0.0435 (14) | 0.0352 (14) |
C15B | 0.0486 (16) | 0.119 (3) | 0.0584 (18) | 0.0184 (17) | 0.0240 (14) | 0.0148 (18) |
C16B | 0.116 (3) | 0.226 (5) | 0.065 (2) | 0.105 (4) | 0.009 (2) | 0.033 (3) |
C6Y | 0.0308 (10) | 0.0377 (11) | 0.0381 (12) | 0.0175 (9) | 0.0135 (9) | 0.0165 (10) |
C5Y | 0.0325 (11) | 0.0362 (12) | 0.0463 (13) | 0.0185 (9) | 0.0055 (10) | 0.0057 (10) |
C4Y | 0.0651 (16) | 0.0664 (16) | 0.0365 (12) | 0.0480 (14) | 0.0117 (12) | 0.0130 (12) |
C3Y | 0.0675 (16) | 0.0664 (16) | 0.0427 (13) | 0.0496 (14) | 0.0272 (12) | 0.0251 (12) |
C2Y | 0.0365 (11) | 0.0385 (12) | 0.0438 (12) | 0.0215 (9) | 0.0188 (10) | 0.0137 (10) |
O2X | 0.0578 (10) | 0.0560 (10) | 0.0596 (11) | 0.0396 (9) | 0.0257 (9) | 0.0278 (9) |
Geometric parameters (Å, º) top
O3Y—C6Y | 1.268 (2) | C1A—C2A | 1.364 (3) |
O1Y—C1Y | 1.270 (2) | C1A—H1 | 0.9300 |
O4X—C6X | 1.315 (3) | C2A—C4A | 1.425 (3) |
O4X—H10' | 0.93 (3) | C2A—C3A | 1.487 (3) |
O3X—C6X | 1.206 (3) | C15A—C16A | 1.488 (4) |
O1X—C1X | 1.203 (3) | C15A—H5 | 0.9700 |
O1A—C3A | 1.204 (3) | C15A—H4 | 0.9700 |
O2A—C3A | 1.321 (3) | C16A—H8 | 0.9600 |
O2A—H9 | 0.91 (4) | C16A—H7 | 0.9600 |
O3A—C4A | 1.264 (3) | C16A—H6 | 0.9600 |
F1A—C7A | 1.354 (2) | C6A—C7A | 1.356 (3) |
N3A—C12A | 1.489 (3) | C6A—H2 | 0.9300 |
N3A—C13A | 1.489 (3) | C11A—C12A | 1.509 (3) |
N3A—H14 | 0.918 (17) | C11A—H10 | 0.9700 |
N3A—H15 | 0.914 (16) | C11A—H11 | 0.9700 |
O2B—C3B | 1.320 (4) | C12A—H13 | 0.9700 |
O2B—H28 | 0.8200 | C12A—H12 | 0.9700 |
O1B—C3B | 1.211 (4) | C13B—C14B | 1.516 (3) |
O3B—C4B | 1.265 (3) | C13B—H36 | 0.9700 |
F1B—C7B | 1.354 (3) | C13B—H35 | 0.9700 |
N3B—C13B | 1.479 (3) | C14B—H37 | 0.9700 |
N3B—C12B | 1.481 (3) | C14B—H38 | 0.9700 |
N3B—H33 | 0.906 (16) | C8B—C9B | 1.377 (3) |
N3B—H34 | 0.917 (16) | C8B—C7B | 1.406 (3) |
O4Y—C6Y | 1.243 (2) | C7B—C6B | 1.361 (3) |
N2A—C8A | 1.404 (3) | C6B—C5B | 1.401 (3) |
N2A—C14A | 1.458 (3) | C6B—H21 | 0.9300 |
N2A—C11A | 1.468 (3) | C5B—C10B | 1.396 (3) |
N1A—C1A | 1.342 (3) | C5B—C4B | 1.459 (3) |
N1A—C10A | 1.400 (3) | C4B—C2B | 1.417 (4) |
N1A—C15A | 1.487 (3) | C2B—C1B | 1.353 (4) |
C5A—C6A | 1.404 (3) | C2B—C3B | 1.492 (4) |
C5A—C10A | 1.409 (3) | C11B—C12B | 1.510 (3) |
C5A—C4A | 1.455 (3) | C11B—H30 | 0.9700 |
N2B—C8B | 1.418 (3) | C11B—H29 | 0.9700 |
N2B—C14B | 1.460 (3) | C12B—H31 | 0.9700 |
N2B—C11B | 1.473 (3) | C12B—H32 | 0.9700 |
C1Y—O2Y | 1.243 (2) | C9B—C10B | 1.406 (3) |
C1Y—C2Y | 1.509 (3) | C9B—H22 | 0.9300 |
C1X—O2X | 1.322 (3) | C10B—N1B | 1.397 (3) |
C1X—C2X | 1.505 (3) | N1B—C1B | 1.345 (3) |
C2X—C3X | 1.507 (3) | N1B—C15B | 1.474 (4) |
C2X—H3' | 0.9700 | C1B—H20 | 0.9300 |
C2X—H2' | 0.9700 | C15B—C16B | 1.468 (5) |
C3X—C4X | 1.522 (3) | C15B—H23 | 1.08 (3) |
C3X—H5' | 0.9700 | C15B—H24 | 1.06 (4) |
C3X—H4' | 0.9700 | C16B—H25 | 0.9600 |
C4X—C5X | 1.516 (3) | C16B—H27 | 0.9600 |
C4X—H7' | 0.9700 | C16B—H26 | 0.9600 |
C4X—H6' | 0.9700 | C6Y—C5Y | 1.509 (3) |
C5X—C6X | 1.500 (3) | C5Y—C4Y | 1.496 (3) |
C5X—H9' | 0.9700 | C5Y—H18' | 0.9700 |
C5X—H8' | 0.9700 | C5Y—H17' | 0.9700 |
C13A—C14A | 1.506 (3) | C4Y—C3Y | 1.522 (3) |
C13A—H17 | 0.9700 | C4Y—H16' | 0.9700 |
C13A—H16 | 0.9700 | C4Y—H15' | 0.9700 |
C14A—H18 | 0.9700 | C3Y—C2Y | 1.497 (3) |
C14A—H19 | 0.9700 | C3Y—H13' | 0.9700 |
C8A—C9A | 1.378 (3) | C3Y—H14' | 0.9700 |
C8A—C7A | 1.407 (3) | C2Y—H11' | 0.9700 |
C9A—C10A | 1.404 (3) | C2Y—H12' | 0.9700 |
C9A—H3 | 0.9300 | O2X—H1' | 0.96 (3) |
| | | |
C6X—O4X—H10' | 109.5 (16) | C6A—C7A—C8A | 122.8 (2) |
C3A—O2A—H9 | 104 (2) | N2A—C11A—C12A | 109.53 (18) |
C12A—N3A—C13A | 112.03 (16) | N2A—C11A—H10 | 109.8 |
C12A—N3A—H14 | 108.9 (16) | C12A—C11A—H10 | 109.8 |
C13A—N3A—H14 | 106.5 (16) | N2A—C11A—H11 | 109.8 |
C12A—N3A—H15 | 112.5 (15) | C12A—C11A—H11 | 109.8 |
C13A—N3A—H15 | 107.2 (15) | H10—C11A—H11 | 108.2 |
H14—N3A—H15 | 109 (2) | N3A—C12A—C11A | 111.11 (17) |
C3B—O2B—H28 | 109.5 | N3A—C12A—H13 | 109.4 |
C13B—N3B—C12B | 110.49 (17) | C11A—C12A—H13 | 109.4 |
C13B—N3B—H33 | 112.2 (15) | N3A—C12A—H12 | 109.4 |
C12B—N3B—H33 | 110.1 (15) | C11A—C12A—H12 | 109.4 |
C13B—N3B—H34 | 110.6 (16) | H13—C12A—H12 | 108.0 |
C12B—N3B—H34 | 107.2 (16) | N3B—C13B—C14B | 109.31 (18) |
H33—N3B—H34 | 106 (2) | N3B—C13B—H36 | 109.8 |
C8A—N2A—C14A | 118.07 (17) | C14B—C13B—H36 | 109.8 |
C8A—N2A—C11A | 117.93 (17) | N3B—C13B—H35 | 109.8 |
C14A—N2A—C11A | 111.41 (16) | C14B—C13B—H35 | 109.8 |
C1A—N1A—C10A | 119.31 (19) | H36—C13B—H35 | 108.3 |
C1A—N1A—C15A | 119.40 (19) | N2B—C14B—C13B | 110.39 (18) |
C10A—N1A—C15A | 121.29 (18) | N2B—C14B—H37 | 109.6 |
C6A—C5A—C10A | 118.47 (19) | C13B—C14B—H37 | 109.6 |
C6A—C5A—C4A | 120.7 (2) | N2B—C14B—H38 | 109.6 |
C10A—C5A—C4A | 120.9 (2) | C13B—C14B—H38 | 109.6 |
C8B—N2B—C14B | 115.58 (17) | H37—C14B—H38 | 108.1 |
C8B—N2B—C11B | 112.37 (17) | C9B—C8B—C7B | 117.02 (19) |
C14B—N2B—C11B | 110.34 (16) | C9B—C8B—N2B | 123.54 (19) |
O2Y—C1Y—O1Y | 123.83 (18) | C7B—C8B—N2B | 119.44 (19) |
O2Y—C1Y—C2Y | 120.14 (18) | F1B—C7B—C6B | 119.2 (2) |
O1Y—C1Y—C2Y | 116.03 (17) | F1B—C7B—C8B | 118.1 (2) |
O1X—C1X—O2X | 123.6 (2) | C6B—C7B—C8B | 122.7 (2) |
O1X—C1X—C2X | 122.2 (2) | C7B—C6B—C5B | 120.2 (2) |
O2X—C1X—C2X | 114.16 (19) | C7B—C6B—H21 | 119.9 |
C1X—C2X—C3X | 116.91 (19) | C5B—C6B—H21 | 119.9 |
C1X—C2X—H3' | 108.1 | C10B—C5B—C6B | 118.4 (2) |
C3X—C2X—H3' | 108.1 | C10B—C5B—C4B | 120.5 (2) |
C1X—C2X—H2' | 108.1 | C6B—C5B—C4B | 121.0 (2) |
C3X—C2X—H2' | 108.1 | O3B—C4B—C2B | 123.3 (2) |
H3'—C2X—H2' | 107.3 | O3B—C4B—C5B | 120.4 (3) |
C2X—C3X—C4X | 112.96 (18) | C2B—C4B—C5B | 116.3 (2) |
C2X—C3X—H5' | 109.0 | C1B—C2B—C4B | 120.0 (2) |
C4X—C3X—H5' | 109.0 | C1B—C2B—C3B | 118.5 (3) |
C2X—C3X—H4' | 109.0 | C4B—C2B—C3B | 121.5 (3) |
C4X—C3X—H4' | 109.0 | O1B—C3B—O2B | 121.7 (3) |
H5'—C3X—H4' | 107.8 | O1B—C3B—C2B | 123.6 (3) |
C5X—C4X—C3X | 111.64 (18) | O2B—C3B—C2B | 114.6 (3) |
C5X—C4X—H7' | 109.3 | N2B—C11B—C12B | 110.97 (18) |
C3X—C4X—H7' | 109.3 | N2B—C11B—H30 | 109.4 |
C5X—C4X—H6' | 109.3 | C12B—C11B—H30 | 109.4 |
C3X—C4X—H6' | 109.3 | N2B—C11B—H29 | 109.4 |
H7'—C4X—H6' | 108.0 | C12B—C11B—H29 | 109.4 |
C6X—C5X—C4X | 115.04 (18) | H30—C11B—H29 | 108.0 |
C6X—C5X—H9' | 108.5 | N3B—C12B—C11B | 109.94 (17) |
C4X—C5X—H9' | 108.5 | N3B—C12B—H31 | 109.7 |
C6X—C5X—H8' | 108.5 | C11B—C12B—H31 | 109.7 |
C4X—C5X—H8' | 108.5 | N3B—C12B—H32 | 109.7 |
H9'—C5X—H8' | 107.5 | C11B—C12B—H32 | 109.7 |
O3X—C6X—O4X | 122.82 (19) | H31—C12B—H32 | 108.2 |
O3X—C6X—C5X | 124.5 (2) | C8B—C9B—C10B | 121.4 (2) |
O4X—C6X—C5X | 112.68 (19) | C8B—C9B—H22 | 119.3 |
N3A—C13A—C14A | 109.33 (17) | C10B—C9B—H22 | 119.3 |
N3A—C13A—H17 | 109.8 | C5B—C10B—N1B | 119.3 (2) |
C14A—C13A—H17 | 109.8 | C5B—C10B—C9B | 120.1 (2) |
N3A—C13A—H16 | 109.8 | N1B—C10B—C9B | 120.6 (2) |
C14A—C13A—H16 | 109.8 | C1B—N1B—C10B | 119.4 (2) |
H17—C13A—H16 | 108.3 | C1B—N1B—C15B | 118.7 (2) |
N2A—C14A—C13A | 107.46 (17) | C10B—N1B—C15B | 121.6 (2) |
N2A—C14A—H18 | 110.2 | N1B—C1B—C2B | 124.4 (3) |
C13A—C14A—H18 | 110.2 | N1B—C1B—H20 | 117.8 |
N2A—C14A—H19 | 110.2 | C2B—C1B—H20 | 117.8 |
C13A—C14A—H19 | 110.2 | C16B—C15B—N1B | 112.2 (3) |
H18—C14A—H19 | 108.5 | C16B—C15B—H23 | 116.3 (17) |
C9A—C8A—N2A | 123.10 (19) | N1B—C15B—H23 | 112.9 (17) |
C9A—C8A—C7A | 117.59 (19) | C16B—C15B—H24 | 117.6 (19) |
N2A—C8A—C7A | 119.13 (19) | N1B—C15B—H24 | 105.4 (19) |
C8A—C9A—C10A | 121.1 (2) | H23—C15B—H24 | 90 (2) |
C8A—C9A—H3 | 119.5 | C15B—C16B—H25 | 109.5 |
C10A—C9A—H3 | 119.5 | C15B—C16B—H27 | 109.5 |
N1A—C10A—C9A | 120.71 (19) | H25—C16B—H27 | 109.5 |
N1A—C10A—C5A | 119.27 (18) | C15B—C16B—H26 | 109.5 |
C9A—C10A—C5A | 120.02 (19) | H25—C16B—H26 | 109.5 |
N1A—C1A—C2A | 124.4 (2) | H27—C16B—H26 | 109.5 |
N1A—C1A—H1 | 117.8 | O4Y—C6Y—O3Y | 124.31 (18) |
C2A—C1A—H1 | 117.8 | O4Y—C6Y—C5Y | 119.05 (19) |
C1A—C2A—C4A | 120.1 (2) | O3Y—C6Y—C5Y | 116.63 (18) |
C1A—C2A—C3A | 118.0 (2) | C4Y—C5Y—C6Y | 116.81 (18) |
C4A—C2A—C3A | 121.8 (2) | C4Y—C5Y—H18' | 108.1 |
O1A—C3A—O2A | 121.3 (2) | C6Y—C5Y—H18' | 108.1 |
O1A—C3A—C2A | 123.6 (2) | C4Y—C5Y—H17' | 108.1 |
O2A—C3A—C2A | 115.1 (2) | C6Y—C5Y—H17' | 108.1 |
N1A—C15A—C16A | 112.6 (2) | H18'—C5Y—H17' | 107.3 |
N1A—C15A—H5 | 109.1 | C5Y—C4Y—C3Y | 113.47 (19) |
C16A—C15A—H5 | 109.1 | C5Y—C4Y—H16' | 108.9 |
N1A—C15A—H4 | 109.1 | C3Y—C4Y—H16' | 108.9 |
C16A—C15A—H4 | 109.1 | C5Y—C4Y—H15' | 108.9 |
H5—C15A—H4 | 107.8 | C3Y—C4Y—H15' | 108.9 |
C15A—C16A—H8 | 109.5 | H16'—C4Y—H15' | 107.7 |
C15A—C16A—H7 | 109.5 | C2Y—C3Y—C4Y | 113.76 (19) |
H8—C16A—H7 | 109.5 | C2Y—C3Y—H13' | 108.8 |
C15A—C16A—H6 | 109.5 | C4Y—C3Y—H13' | 108.8 |
H8—C16A—H6 | 109.5 | C2Y—C3Y—H14' | 108.8 |
H7—C16A—H6 | 109.5 | C4Y—C3Y—H14' | 108.8 |
O3A—C4A—C2A | 122.9 (2) | H13'—C3Y—H14' | 107.7 |
O3A—C4A—C5A | 121.3 (2) | C3Y—C2Y—C1Y | 116.22 (17) |
C2A—C4A—C5A | 115.8 (2) | C3Y—C2Y—H11' | 108.2 |
C7A—C6A—C5A | 120.0 (2) | C1Y—C2Y—H11' | 108.2 |
C7A—C6A—H2 | 120.0 | C3Y—C2Y—H12' | 108.2 |
C5A—C6A—H2 | 120.0 | C1Y—C2Y—H12' | 108.2 |
F1A—C7A—C6A | 119.8 (2) | H11'—C2Y—H12' | 107.4 |
F1A—C7A—C8A | 117.36 (18) | C1X—O2X—H1' | 112.4 (18) |
| | | |
O1X—C1X—C2X—C3X | −169.5 (2) | C12B—N3B—C13B—C14B | −58.6 (2) |
O2X—C1X—C2X—C3X | 9.5 (3) | C8B—N2B—C14B—C13B | 172.39 (18) |
C1X—C2X—C3X—C4X | 176.68 (19) | C11B—N2B—C14B—C13B | −58.8 (2) |
C2X—C3X—C4X—C5X | −175.54 (19) | N3B—C13B—C14B—N2B | 59.3 (2) |
C3X—C4X—C5X—C6X | 172.96 (19) | C14B—N2B—C8B—C9B | 16.1 (3) |
C4X—C5X—C6X—O3X | 5.3 (3) | C11B—N2B—C8B—C9B | −111.7 (2) |
C4X—C5X—C6X—O4X | −173.46 (18) | C14B—N2B—C8B—C7B | −164.4 (2) |
C12A—N3A—C13A—C14A | 56.5 (2) | C11B—N2B—C8B—C7B | 67.7 (3) |
C8A—N2A—C14A—C13A | −154.21 (18) | C9B—C8B—C7B—F1B | −176.6 (2) |
C11A—N2A—C14A—C13A | 64.6 (2) | N2B—C8B—C7B—F1B | 3.9 (3) |
N3A—C13A—C14A—N2A | −61.1 (2) | C9B—C8B—C7B—C6B | 3.9 (3) |
C14A—N2A—C8A—C9A | −24.0 (3) | N2B—C8B—C7B—C6B | −175.6 (2) |
C11A—N2A—C8A—C9A | 114.7 (2) | F1B—C7B—C6B—C5B | 179.4 (2) |
C14A—N2A—C8A—C7A | 151.1 (2) | C8B—C7B—C6B—C5B | −1.1 (4) |
C11A—N2A—C8A—C7A | −70.2 (3) | C7B—C6B—C5B—C10B | −2.1 (3) |
N2A—C8A—C9A—C10A | 173.2 (2) | C7B—C6B—C5B—C4B | 175.6 (2) |
C7A—C8A—C9A—C10A | −1.9 (3) | C10B—C5B—C4B—O3B | 176.5 (2) |
C1A—N1A—C10A—C9A | 176.8 (2) | C6B—C5B—C4B—O3B | −1.1 (3) |
C15A—N1A—C10A—C9A | −4.3 (3) | C10B—C5B—C4B—C2B | −2.3 (3) |
C1A—N1A—C10A—C5A | −4.2 (3) | C6B—C5B—C4B—C2B | −179.9 (2) |
C15A—N1A—C10A—C5A | 174.7 (2) | O3B—C4B—C2B—C1B | −177.9 (2) |
C8A—C9A—C10A—N1A | 179.3 (2) | C5B—C4B—C2B—C1B | 0.9 (3) |
C8A—C9A—C10A—C5A | 0.3 (3) | O3B—C4B—C2B—C3B | 0.8 (4) |
C6A—C5A—C10A—N1A | −177.7 (2) | C5B—C4B—C2B—C3B | 179.5 (2) |
C4A—C5A—C10A—N1A | 3.1 (3) | C1B—C2B—C3B—O1B | −3.6 (4) |
C6A—C5A—C10A—C9A | 1.4 (3) | C4B—C2B—C3B—O1B | 177.8 (3) |
C4A—C5A—C10A—C9A | −177.8 (2) | C1B—C2B—C3B—O2B | 176.6 (2) |
C10A—N1A—C1A—C2A | 1.5 (4) | C4B—C2B—C3B—O2B | −2.0 (4) |
C15A—N1A—C1A—C2A | −177.4 (2) | C8B—N2B—C11B—C12B | −171.82 (18) |
N1A—C1A—C2A—C4A | 2.2 (4) | C14B—N2B—C11B—C12B | 57.6 (2) |
N1A—C1A—C2A—C3A | 179.9 (2) | C13B—N3B—C12B—C11B | 57.5 (2) |
C1A—C2A—C3A—O1A | 2.3 (4) | N2B—C11B—C12B—N3B | −56.6 (2) |
C4A—C2A—C3A—O1A | 180.0 (2) | C7B—C8B—C9B—C10B | −3.4 (3) |
C1A—C2A—C3A—O2A | −176.7 (2) | N2B—C8B—C9B—C10B | 176.0 (2) |
C4A—C2A—C3A—O2A | 0.9 (3) | C6B—C5B—C10B—N1B | −179.3 (2) |
C1A—N1A—C15A—C16A | −97.2 (3) | C4B—C5B—C10B—N1B | 3.0 (3) |
C10A—N1A—C15A—C16A | 83.9 (3) | C6B—C5B—C10B—C9B | 2.5 (3) |
C1A—C2A—C4A—O3A | 177.0 (2) | C4B—C5B—C10B—C9B | −175.2 (2) |
C3A—C2A—C4A—O3A | −0.6 (3) | C8B—C9B—C10B—C5B | 0.3 (3) |
C1A—C2A—C4A—C5A | −3.1 (3) | C8B—C9B—C10B—N1B | −177.8 (2) |
C3A—C2A—C4A—C5A | 179.3 (2) | C5B—C10B—N1B—C1B | −2.3 (3) |
C6A—C5A—C4A—O3A | 1.2 (3) | C9B—C10B—N1B—C1B | 175.9 (2) |
C10A—C5A—C4A—O3A | −179.6 (2) | C5B—C10B—N1B—C15B | −176.3 (3) |
C6A—C5A—C4A—C2A | −178.7 (2) | C9B—C10B—N1B—C15B | 1.8 (4) |
C10A—C5A—C4A—C2A | 0.5 (3) | C10B—N1B—C1B—C2B | 1.0 (4) |
C10A—C5A—C6A—C7A | −1.3 (3) | C15B—N1B—C1B—C2B | 175.2 (3) |
C4A—C5A—C6A—C7A | 177.9 (2) | C4B—C2B—C1B—N1B | −0.3 (4) |
C5A—C6A—C7A—F1A | −177.1 (2) | C3B—C2B—C1B—N1B | −178.9 (2) |
C5A—C6A—C7A—C8A | −0.4 (4) | C1B—N1B—C15B—C16B | −92.1 (3) |
C9A—C8A—C7A—F1A | 178.8 (2) | C10B—N1B—C15B—C16B | 82.0 (3) |
N2A—C8A—C7A—F1A | 3.5 (3) | O4Y—C6Y—C5Y—C4Y | 6.8 (3) |
C9A—C8A—C7A—C6A | 2.0 (3) | O3Y—C6Y—C5Y—C4Y | −174.2 (2) |
N2A—C8A—C7A—C6A | −173.3 (2) | C6Y—C5Y—C4Y—C3Y | 170.3 (2) |
C8A—N2A—C11A—C12A | 158.14 (19) | C5Y—C4Y—C3Y—C2Y | 58.2 (3) |
C14A—N2A—C11A—C12A | −60.6 (2) | C4Y—C3Y—C2Y—C1Y | 171.8 (2) |
C13A—N3A—C12A—C11A | −52.4 (2) | O2Y—C1Y—C2Y—C3Y | 5.6 (3) |
N2A—C11A—C12A—N3A | 53.0 (2) | O1Y—C1Y—C2Y—C3Y | −174.5 (2) |
Crystal data top
C41H57F2N6O21 | V = 2204.38 (13) Å3 |
Mr = 1007.93 | Z = 2 |
Triclinic, P1 | F(000) = 1062 |
a = 7.4031 (3) Å | Dx = 1.518 Mg m−3 |
b = 9.7515 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 30.9801 (10) Å | µ = 0.13 mm−1 |
α = 88.088 (2)° | T = 100 K |
β = 85.673 (2)° | Needle, colorless |
γ = 81.380 (2)° | 0.21 × 0.08 × 0.05 mm |
Data collection top
CCD area detector diffractometer | 4274 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.059 |
Graphite monochromator | θmax = 25.0°, θmin = 1.3° |
phi and ω scans | h = −8→8 |
31596 measured reflections | k = −11→11 |
7784 independent reflections | l = −36→36 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.131 | H 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 parameters | Δρmax = 0.41 e Å−3 |
14 restraints | Δρmin = −0.31 e Å−3 |
Crystal data top
C41H57F2N6O21 | γ = 81.380 (2)° |
Mr = 1007.93 | V = 2204.38 (13) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.4031 (3) Å | Mo Kα radiation |
b = 9.7515 (3) Å | µ = 0.13 mm−1 |
c = 30.9801 (10) Å | T = 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 reflections | Rint = 0.059 |
7784 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.052 | 14 restraints |
wR(F2) = 0.131 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.41 e Å−3 |
7784 reflections | Δρmin = −0.31 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
H2B | 0.333 (7) | 0.926 (5) | 0.9142 (16) | 0.122 (19)* | |
H2A | 0.325 (5) | 0.835 (4) | 0.9506 (12) | 0.072 (15)* | |
O2S | 0.3966 (3) | 0.8792 (3) | 0.93735 (9) | 0.0513 (7) | |
O1Y | 0.8893 (3) | 0.2461 (2) | 1.02422 (7) | 0.0405 (6) | |
O3Y | 0.7950 (3) | 0.5381 (2) | 0.95190 (7) | 0.0511 (7) | |
H1' | 0.8611 | 0.4888 | 0.9343 | 0.077* | |
O4Y | 0.5320 (3) | 0.3592 (2) | 0.96084 (7) | 0.0419 (6) | |
H4Y | 0.4260 | 0.3433 | 0.9635 | 0.063* | |
O2Y | 1.0077 (3) | 0.3019 (2) | 0.95873 (7) | 0.0414 (6) | |
C1Y | 0.8976 (4) | 0.3251 (3) | 0.99085 (10) | 0.0293 (8) | |
C2Y | 0.7658 (4) | 0.4600 (3) | 0.99086 (10) | 0.0319 (8) | |
H2' | 0.7906 | 0.5147 | 1.0151 | 0.038* | |
C3Y | 0.5681 (4) | 0.4335 (3) | 0.99746 (9) | 0.0293 (8) | |
H3' | 0.5552 | 0.3750 | 1.0235 | 0.035* | |
O3X | 0.5823 (3) | 0.1571 (2) | 0.43764 (7) | 0.0369 (6) | |
H6' | 0.6554 | 0.2116 | 0.4318 | 0.055* | |
O4X | 0.6539 (2) | 0.0815 (2) | 0.52956 (6) | 0.0296 (5) | |
H8' | 0.7656 | 0.0702 | 0.5303 | 0.044* | |
O1S | 0.3279 (4) | 0.1470 (3) | 0.97959 (8) | 0.0450 (7) | |
O2A | 1.2065 (4) | 0.1025 (3) | 0.88170 (8) | 0.0639 (8) | |
H1 | 1.1627 | 0.1847 | 0.8802 | 0.096* | |
O1A | 1.2958 (4) | −0.0690 (3) | 0.83684 (9) | 0.0705 (9) | |
F1A | 0.7822 (3) | 0.7158 (2) | 0.75906 (6) | 0.0520 (5) | |
O2B | 0.3489 (3) | 0.6531 (3) | 0.67071 (8) | 0.0521 (7) | |
O1B | 0.2921 (5) | 0.8080 (3) | 0.72134 (9) | 0.0818 (10) | |
F1B | 0.8147 (3) | 0.00155 (19) | 0.77003 (5) | 0.0505 (5) | |
O1X | 0.9884 (3) | −0.0765 (2) | 0.45757 (6) | 0.0313 (5) | |
O2X | 0.9322 (3) | 0.1462 (2) | 0.43767 (7) | 0.0418 (6) | |
O1Z | 0.1139 (3) | 0.3142 (3) | 0.52312 (7) | 0.0418 (6) | |
O4Z | 0.5887 (3) | 0.3643 (2) | 0.53742 (7) | 0.0400 (6) | |
H12' | 0.615 (5) | 0.281 (4) | 0.5310 (11) | 0.060* | |
N2A | 0.8575 (3) | 0.6311 (3) | 0.67358 (7) | 0.0329 (7) | |
N1A | 1.1772 (4) | 0.1980 (3) | 0.73092 (8) | 0.0372 (6) | |
O3A | 1.0445 (3) | 0.3286 (3) | 0.85514 (7) | 0.0565 (7) | |
N2B | 0.7639 (3) | 0.0598 (2) | 0.85922 (7) | 0.0281 (6) | |
N3B | 0.8142 (3) | −0.1320 (3) | 0.93231 (7) | 0.0352 (7) | |
H34 | 0.6979 | −0.1417 | 0.9410 | 0.042* | |
H33 | 0.8888 | −0.1853 | 0.9498 | 0.042* | |
O3B | 0.5025 (3) | 0.4101 (2) | 0.68871 (7) | 0.0444 (6) | |
O2Z | 0.1984 (3) | 0.3199 (3) | 0.59078 (8) | 0.0585 (7) | |
N3A | 0.7474 (4) | 0.7978 (3) | 0.59967 (9) | 0.0398 (8) | |
C12A | 0.7312 (4) | 0.8547 (3) | 0.64372 (11) | 0.0443 (9) | |
H13 | 0.6114 | 0.8458 | 0.6575 | 0.053* | |
H12 | 0.7427 | 0.9525 | 0.6418 | 0.053* | |
C11A | 0.8768 (5) | 0.7794 (3) | 0.67058 (10) | 0.0404 (9) | |
H10 | 0.9969 | 0.7904 | 0.6574 | 0.048* | |
H11 | 0.8645 | 0.8177 | 0.6993 | 0.048* | |
C8A | 0.9284 (4) | 0.5491 (3) | 0.70795 (9) | 0.0285 (8) | |
C9A | 1.0300 (4) | 0.4190 (3) | 0.70216 (9) | 0.0297 (8) | |
H8 | 1.0650 | 0.3890 | 0.6742 | 0.036* | |
C10A | 1.0815 (4) | 0.3314 (3) | 0.73714 (9) | 0.0278 (7) | |
C1A | 1.2175 (4) | 0.1148 (4) | 0.76530 (11) | 0.0414 (9) | |
H2 | 1.2771 | 0.0253 | 0.7602 | 0.050* | |
C2A | 1.1764 (4) | 0.1531 (4) | 0.80742 (10) | 0.0382 (9) | |
C3A | 1.2312 (5) | 0.0514 (5) | 0.84246 (12) | 0.0494 (10) | |
C15A | 1.2331 (5) | 0.1443 (4) | 0.68672 (10) | 0.0452 (7) | |
H4 | 1.2732 | 0.2179 | 0.6683 | 0.054* | |
H3 | 1.3354 | 0.0699 | 0.6882 | 0.054* | |
C16A | 1.0805 (5) | 0.0924 (4) | 0.66773 (11) | 0.0605 (10) | |
H5 | 1.0345 | 0.0246 | 0.6870 | 0.091* | |
H6 | 1.1230 | 0.0507 | 0.6405 | 0.091* | |
H7 | 0.9843 | 0.1682 | 0.6633 | 0.091* | |
C5A | 1.0367 (4) | 0.3767 (3) | 0.77983 (9) | 0.0320 (8) | |
C4A | 1.0853 (4) | 0.2871 (4) | 0.81688 (11) | 0.0383 (9) | |
C6A | 0.9397 (4) | 0.5104 (4) | 0.78577 (10) | 0.0368 (8) | |
H9 | 0.9113 | 0.5437 | 0.8136 | 0.044* | |
C7A | 0.8873 (4) | 0.5912 (3) | 0.75141 (10) | 0.0351 (8) | |
C13A | 0.7483 (4) | 0.6455 (3) | 0.60107 (10) | 0.0406 (9) | |
H16 | 0.7761 | 0.6102 | 0.5721 | 0.049* | |
H17 | 0.6271 | 0.6260 | 0.6110 | 0.049* | |
C14A | 0.8859 (4) | 0.5715 (3) | 0.63048 (9) | 0.0359 (8) | |
H19 | 0.8737 | 0.4738 | 0.6326 | 0.043* | |
H18 | 1.0088 | 0.5794 | 0.6184 | 0.043* | |
C3B | 0.3466 (5) | 0.6907 (4) | 0.71129 (12) | 0.0463 (9) | |
C2B | 0.4164 (4) | 0.5785 (3) | 0.74194 (10) | 0.0347 (8) | |
C4B | 0.4923 (4) | 0.4445 (3) | 0.72801 (10) | 0.0327 (8) | |
C5B | 0.5596 (4) | 0.3467 (3) | 0.76188 (9) | 0.0294 (8) | |
C6B | 0.6495 (4) | 0.2134 (3) | 0.75146 (9) | 0.0322 (8) | |
H21 | 0.6638 | 0.1864 | 0.7228 | 0.039* | |
C7B | 0.7154 (4) | 0.1241 (3) | 0.78281 (10) | 0.0312 (8) | |
C8B | 0.6919 (4) | 0.1536 (3) | 0.82764 (9) | 0.0277 (7) | |
C11B | 0.7384 (5) | −0.0864 (3) | 0.85643 (10) | 0.0377 (8) | |
H30 | 0.7705 | −0.1171 | 0.8270 | 0.045* | |
H29 | 0.6105 | −0.0948 | 0.8635 | 0.045* | |
C12B | 0.8556 (4) | −0.1783 (3) | 0.88711 (9) | 0.0377 (8) | |
H31 | 0.8332 | −0.2733 | 0.8852 | 0.045* | |
H32 | 0.9839 | −0.1756 | 0.8787 | 0.045* | |
C1B | 0.4101 (4) | 0.6100 (4) | 0.78500 (11) | 0.0425 (9) | |
H28 | 0.3611 | 0.6996 | 0.7931 | 0.051* | |
N1B | 0.4705 (4) | 0.5194 (3) | 0.81605 (8) | 0.0392 (7) | |
C10B | 0.5440 (4) | 0.3837 (3) | 0.80550 (10) | 0.0308 (8) | |
C13B | 0.8394 (5) | 0.0145 (3) | 0.93556 (10) | 0.0373 (8) | |
H36 | 0.9681 | 0.0222 | 0.9298 | 0.045* | |
H35 | 0.8030 | 0.0449 | 0.9648 | 0.045* | |
C14B | 0.7290 (4) | 0.1084 (3) | 0.90421 (9) | 0.0334 (8) | |
H37 | 0.5997 | 0.1124 | 0.9129 | 0.040* | |
H38 | 0.7595 | 0.2014 | 0.9054 | 0.040* | |
C9B | 0.6035 (4) | 0.2858 (3) | 0.83745 (9) | 0.0322 (8) | |
H22 | 0.5830 | 0.3103 | 0.8663 | 0.039* | |
C15B | 0.4569 (5) | 0.5708 (4) | 0.86199 (10) | 0.0503 (10) | |
H23 | 0.5571 | 0.5218 | 0.8775 | 0.060* | |
H24 | 0.4666 | 0.6689 | 0.8615 | 0.060* | |
C16B | 0.2815 (6) | 0.5480 (5) | 0.88439 (13) | 0.0742 (13) | |
H25 | 0.1830 | 0.5870 | 0.8672 | 0.111* | |
H26 | 0.2672 | 0.5919 | 0.9120 | 0.111* | |
H27 | 0.2797 | 0.4503 | 0.8886 | 0.111* | |
C1X | 0.8834 (4) | 0.0320 (3) | 0.44884 (9) | 0.0250 (7) | |
C2X | 0.6776 (4) | 0.0282 (3) | 0.45211 (9) | 0.0243 (7) | |
H5' | 0.6538 | −0.0440 | 0.4329 | 0.029* | |
C3X | 0.6045 (3) | −0.0070 (3) | 0.49800 (9) | 0.0216 (7) | |
H7' | 0.6548 | −0.1031 | 0.5052 | 0.026* | |
C1Z | 0.1923 (4) | 0.3659 (3) | 0.55439 (11) | 0.0333 (8) | |
C2Z | 0.2832 (4) | 0.4898 (3) | 0.53881 (9) | 0.0315 (8) | |
H11' | 0.1993 | 0.5524 | 0.5215 | 0.038* | |
C3Z | 0.4582 (4) | 0.4394 (3) | 0.51077 (9) | 0.0282 (7) | |
H13' | 0.4301 | 0.3785 | 0.4884 | 0.034* | |
H15 | 0.863 (6) | 0.817 (4) | 0.5863 (12) | 0.082 (13)* | |
H14 | 0.649 (5) | 0.830 (4) | 0.5860 (10) | 0.056 (11)* | |
O3S | 0.6622 (7) | 0.2085 (5) | 0.62770 (12) | 0.173 (2) | |
H3A | 0.6493 | 0.2493 | 0.6032 | 0.259* | |
H3B | 0.6426 | 0.2701 | 0.6469 | 0.259* | |
H1B | 0.214 (6) | 0.193 (4) | 0.9707 (12) | 0.083 (15)* | |
H1A | 0.356 (7) | 0.068 (5) | 0.9669 (16) | 0.12 (2)* | |
H9' | 0.074 (5) | 0.233 (4) | 0.5329 (12) | 0.081 (14)* | |
H20 | 0.396 (5) | 0.556 (4) | 0.6688 (11) | 0.063 (13)* | |
O3Z | 0.3255 (3) | 0.5618 (2) | 0.57498 (7) | 0.0463 (6) | |
H10' | 0.3619 | 0.5056 | 0.5939 | 0.069* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2S | 0.0418 (16) | 0.0528 (19) | 0.0588 (18) | −0.0096 (14) | −0.0060 (14) | 0.0240 (14) |
O1Y | 0.0354 (13) | 0.0401 (15) | 0.0438 (13) | −0.0014 (11) | −0.0050 (11) | 0.0163 (11) |
O3Y | 0.0431 (16) | 0.0450 (16) | 0.0607 (16) | −0.0021 (12) | 0.0045 (12) | 0.0258 (13) |
O4Y | 0.0313 (13) | 0.0465 (15) | 0.0482 (14) | −0.0055 (11) | 0.0002 (11) | −0.0144 (12) |
O2Y | 0.0351 (13) | 0.0449 (16) | 0.0403 (14) | 0.0028 (12) | 0.0058 (11) | −0.0009 (11) |
C1Y | 0.0214 (17) | 0.031 (2) | 0.0367 (19) | −0.0055 (15) | −0.0066 (15) | 0.0000 (16) |
C2Y | 0.0292 (18) | 0.029 (2) | 0.0360 (18) | −0.0017 (16) | −0.0022 (14) | 0.0064 (15) |
C3Y | 0.0327 (19) | 0.0235 (19) | 0.0315 (18) | −0.0037 (14) | −0.0030 (15) | 0.0007 (15) |
O3X | 0.0238 (12) | 0.0345 (14) | 0.0526 (14) | −0.0077 (11) | −0.0063 (10) | 0.0209 (11) |
O4X | 0.0149 (10) | 0.0367 (14) | 0.0381 (12) | −0.0044 (10) | −0.0035 (9) | −0.0057 (10) |
O1S | 0.0390 (16) | 0.0474 (19) | 0.0480 (15) | −0.0050 (14) | −0.0016 (12) | −0.0021 (14) |
O2A | 0.0687 (19) | 0.082 (2) | 0.0447 (16) | −0.0219 (18) | −0.0208 (14) | 0.0332 (15) |
O1A | 0.0666 (19) | 0.061 (2) | 0.079 (2) | 0.0027 (17) | −0.0167 (15) | 0.0390 (17) |
F1A | 0.0683 (14) | 0.0350 (13) | 0.0487 (12) | 0.0026 (11) | 0.0036 (10) | −0.0058 (10) |
O2B | 0.0572 (17) | 0.057 (2) | 0.0402 (16) | −0.0042 (15) | −0.0074 (12) | 0.0151 (14) |
O1B | 0.134 (3) | 0.0415 (19) | 0.0628 (18) | 0.016 (2) | −0.0245 (18) | 0.0125 (15) |
F1B | 0.0719 (14) | 0.0332 (12) | 0.0395 (11) | 0.0107 (11) | 0.0047 (10) | −0.0030 (9) |
O1X | 0.0176 (11) | 0.0286 (14) | 0.0481 (13) | −0.0039 (10) | −0.0036 (10) | −0.0002 (10) |
O2X | 0.0257 (12) | 0.0384 (15) | 0.0611 (15) | −0.0100 (11) | 0.0009 (11) | 0.0164 (12) |
O1Z | 0.0406 (14) | 0.0365 (16) | 0.0521 (15) | −0.0174 (12) | −0.0054 (12) | 0.0011 (13) |
O4Z | 0.0405 (14) | 0.0300 (14) | 0.0478 (14) | 0.0011 (13) | −0.0080 (11) | 0.0047 (12) |
N2A | 0.0431 (17) | 0.0264 (16) | 0.0299 (15) | −0.0069 (13) | −0.0065 (12) | 0.0055 (12) |
N1A | 0.0484 (15) | 0.0273 (15) | 0.0342 (12) | −0.0005 (12) | −0.0061 (12) | 0.0091 (11) |
O3A | 0.0779 (19) | 0.0683 (19) | 0.0277 (14) | −0.0241 (15) | −0.0102 (13) | 0.0071 (13) |
N2B | 0.0344 (15) | 0.0212 (15) | 0.0280 (14) | −0.0016 (12) | −0.0028 (11) | 0.0011 (12) |
N3B | 0.0365 (16) | 0.0327 (17) | 0.0340 (15) | −0.0002 (13) | −0.0011 (12) | 0.0102 (13) |
O3B | 0.0554 (15) | 0.0491 (16) | 0.0286 (13) | −0.0068 (13) | −0.0059 (11) | 0.0035 (11) |
O2Z | 0.0802 (19) | 0.0579 (18) | 0.0410 (15) | −0.0280 (15) | 0.0037 (13) | 0.0092 (13) |
N3A | 0.0218 (17) | 0.050 (2) | 0.0473 (19) | −0.0057 (15) | −0.0082 (15) | 0.0218 (16) |
C12A | 0.041 (2) | 0.031 (2) | 0.059 (2) | −0.0034 (18) | −0.0023 (18) | 0.0119 (18) |
C11A | 0.050 (2) | 0.029 (2) | 0.045 (2) | −0.0125 (17) | −0.0101 (17) | 0.0113 (16) |
C8A | 0.0289 (18) | 0.027 (2) | 0.0304 (18) | −0.0065 (16) | −0.0044 (14) | 0.0055 (15) |
C9A | 0.0334 (19) | 0.031 (2) | 0.0253 (17) | −0.0057 (16) | −0.0019 (14) | 0.0009 (15) |
C10A | 0.0284 (18) | 0.027 (2) | 0.0289 (18) | −0.0079 (15) | −0.0036 (14) | 0.0059 (15) |
C1A | 0.040 (2) | 0.031 (2) | 0.052 (2) | −0.0050 (17) | −0.0069 (17) | 0.0127 (18) |
C2A | 0.036 (2) | 0.044 (2) | 0.037 (2) | −0.0127 (18) | −0.0126 (16) | 0.0196 (18) |
C3A | 0.039 (2) | 0.065 (3) | 0.048 (3) | −0.020 (2) | −0.0120 (19) | 0.025 (2) |
C15A | 0.0591 (17) | 0.0336 (16) | 0.0395 (13) | 0.0024 (14) | −0.0024 (13) | 0.0058 (12) |
C16A | 0.081 (2) | 0.050 (2) | 0.054 (2) | −0.0178 (19) | −0.0044 (18) | −0.0011 (18) |
C5A | 0.0346 (19) | 0.033 (2) | 0.0311 (18) | −0.0142 (17) | −0.0066 (15) | 0.0079 (16) |
C4A | 0.038 (2) | 0.046 (3) | 0.036 (2) | −0.0214 (19) | −0.0077 (16) | 0.0101 (18) |
C6A | 0.045 (2) | 0.040 (2) | 0.0272 (18) | −0.0152 (19) | −0.0007 (15) | 0.0000 (16) |
C7A | 0.038 (2) | 0.025 (2) | 0.042 (2) | −0.0037 (17) | 0.0002 (16) | −0.0027 (16) |
C13A | 0.039 (2) | 0.045 (2) | 0.040 (2) | −0.0134 (18) | −0.0094 (16) | 0.0128 (17) |
C14A | 0.041 (2) | 0.035 (2) | 0.0322 (18) | −0.0053 (17) | −0.0046 (15) | 0.0050 (16) |
C3B | 0.050 (2) | 0.046 (3) | 0.042 (2) | −0.005 (2) | −0.0054 (18) | 0.011 (2) |
C2B | 0.0317 (19) | 0.034 (2) | 0.036 (2) | 0.0007 (17) | −0.0010 (15) | 0.0081 (16) |
C4B | 0.0251 (18) | 0.037 (2) | 0.036 (2) | −0.0083 (16) | 0.0015 (15) | 0.0070 (17) |
C5B | 0.0279 (18) | 0.027 (2) | 0.0327 (18) | −0.0058 (16) | −0.0004 (14) | 0.0056 (15) |
C6B | 0.0362 (19) | 0.035 (2) | 0.0256 (17) | −0.0068 (17) | −0.0002 (14) | −0.0019 (15) |
C7B | 0.0352 (19) | 0.0218 (19) | 0.0341 (19) | 0.0017 (16) | 0.0021 (15) | −0.0008 (15) |
C8B | 0.0233 (17) | 0.030 (2) | 0.0294 (18) | −0.0026 (15) | −0.0013 (14) | 0.0028 (15) |
C11B | 0.049 (2) | 0.026 (2) | 0.0390 (19) | −0.0048 (17) | −0.0072 (16) | 0.0030 (15) |
C12B | 0.043 (2) | 0.028 (2) | 0.039 (2) | 0.0029 (17) | 0.0009 (16) | 0.0017 (16) |
C1B | 0.048 (2) | 0.030 (2) | 0.045 (2) | 0.0064 (17) | −0.0015 (17) | 0.0078 (17) |
N1B | 0.0539 (19) | 0.0276 (18) | 0.0310 (15) | 0.0091 (15) | −0.0008 (13) | 0.0026 (13) |
C10B | 0.0323 (19) | 0.026 (2) | 0.0336 (19) | −0.0023 (16) | 0.0004 (15) | −0.0001 (15) |
C13B | 0.050 (2) | 0.031 (2) | 0.0326 (18) | −0.0079 (17) | −0.0081 (16) | 0.0071 (15) |
C14B | 0.041 (2) | 0.029 (2) | 0.0280 (18) | −0.0021 (16) | −0.0002 (15) | 0.0017 (15) |
C9B | 0.0348 (19) | 0.033 (2) | 0.0269 (17) | −0.0005 (17) | 0.0003 (14) | 0.0019 (15) |
C15B | 0.074 (3) | 0.026 (2) | 0.042 (2) | 0.015 (2) | 0.005 (2) | 0.0007 (17) |
C16B | 0.074 (3) | 0.083 (4) | 0.064 (3) | −0.001 (3) | −0.010 (2) | −0.016 (2) |
C1X | 0.0236 (17) | 0.027 (2) | 0.0238 (16) | −0.0045 (16) | 0.0009 (13) | 0.0006 (14) |
C2X | 0.0195 (16) | 0.0233 (18) | 0.0297 (17) | −0.0036 (14) | 0.0001 (13) | 0.0043 (14) |
C3X | 0.0165 (15) | 0.0183 (17) | 0.0298 (16) | −0.0021 (14) | −0.0024 (13) | −0.0001 (13) |
C1Z | 0.0289 (19) | 0.030 (2) | 0.041 (2) | −0.0069 (16) | 0.0048 (16) | −0.0066 (17) |
C2Z | 0.0334 (19) | 0.027 (2) | 0.0349 (18) | −0.0074 (16) | 0.0022 (15) | −0.0046 (15) |
C3Z | 0.0318 (19) | 0.0219 (18) | 0.0315 (17) | −0.0054 (15) | −0.0021 (14) | −0.0021 (14) |
O3S | 0.231 (5) | 0.155 (4) | 0.104 (3) | 0.062 (4) | −0.016 (3) | −0.007 (3) |
O3Z | 0.0557 (16) | 0.0410 (15) | 0.0445 (14) | −0.0179 (14) | 0.0095 (12) | −0.0162 (12) |
Geometric parameters (Å, º) top
O2S—H2B | 0.95 (5) | C1A—H2 | 0.9300 |
O2S—H2A | 0.81 (4) | C2A—C4A | 1.407 (5) |
O1Y—C1Y | 1.272 (3) | C2A—C3A | 1.483 (5) |
O3Y—C2Y | 1.425 (3) | C15A—C16A | 1.473 (4) |
O3Y—H1' | 0.8200 | C15A—H4 | 0.9700 |
O4Y—C3Y | 1.429 (3) | C15A—H3 | 0.9700 |
O4Y—H4Y | 0.8200 | C16A—H5 | 0.9600 |
O2Y—C1Y | 1.242 (3) | C16A—H6 | 0.9600 |
C1Y—C2Y | 1.516 (4) | C16A—H7 | 0.9600 |
C2Y—C3Y | 1.522 (4) | C5A—C6A | 1.402 (4) |
C2Y—H2' | 0.9800 | C5A—C4A | 1.453 (4) |
C3Y—C3Yi | 1.523 (6) | C6A—C7A | 1.348 (4) |
C3Y—H3' | 0.9800 | C6A—H9 | 0.9300 |
O3X—C2X | 1.422 (3) | C13A—C14A | 1.505 (4) |
O3X—H6' | 0.8200 | C13A—H16 | 0.9700 |
O4X—C3X | 1.428 (3) | C13A—H17 | 0.9700 |
O4X—H8' | 0.8200 | C14A—H19 | 0.9700 |
O1S—H1B | 0.95 (4) | C14A—H18 | 0.9700 |
O1S—H1A | 0.87 (5) | C3B—C2B | 1.483 (5) |
O2A—C3A | 1.318 (4) | C2B—C1B | 1.375 (4) |
O2A—H1 | 0.8200 | C2B—C4B | 1.411 (4) |
O1A—C3A | 1.213 (4) | C4B—C5B | 1.459 (4) |
F1A—C7A | 1.359 (3) | C5B—C10B | 1.402 (4) |
O2B—C3B | 1.320 (4) | C5B—C6B | 1.405 (4) |
O2B—H20 | 0.96 (4) | C6B—C7B | 1.352 (4) |
O1B—C3B | 1.198 (4) | C6B—H21 | 0.9300 |
F1B—C7B | 1.360 (3) | C7B—C8B | 1.420 (4) |
O1X—C1X | 1.251 (3) | C8B—C9B | 1.388 (4) |
O2X—C1X | 1.251 (3) | C11B—C12B | 1.514 (4) |
O1Z—C1Z | 1.317 (4) | C11B—H30 | 0.9700 |
O1Z—H9' | 0.92 (4) | C11B—H29 | 0.9700 |
O4Z—C3Z | 1.422 (3) | C12B—H31 | 0.9700 |
O4Z—H12' | 0.83 (4) | C12B—H32 | 0.9700 |
N2A—C8A | 1.397 (3) | C1B—N1B | 1.340 (4) |
N2A—C14A | 1.462 (4) | C1B—H28 | 0.9300 |
N2A—C11A | 1.473 (4) | N1B—C10B | 1.393 (4) |
N1A—C1A | 1.342 (4) | N1B—C15B | 1.516 (4) |
N1A—C10A | 1.397 (4) | C10B—C9B | 1.401 (4) |
N1A—C15A | 1.489 (4) | C13B—C14B | 1.511 (4) |
O3A—C4A | 1.266 (4) | C13B—H36 | 0.9700 |
N2B—C8B | 1.397 (4) | C13B—H35 | 0.9700 |
N2B—C11B | 1.472 (4) | C14B—H37 | 0.9700 |
N2B—C14B | 1.479 (4) | C14B—H38 | 0.9700 |
N3B—C13B | 1.477 (4) | C9B—H22 | 0.9300 |
N3B—C12B | 1.481 (4) | C15B—C16B | 1.468 (5) |
N3B—H34 | 0.9000 | C15B—H23 | 0.9700 |
N3B—H33 | 0.9000 | C15B—H24 | 0.9700 |
O3B—C4B | 1.268 (3) | C16B—H25 | 0.9600 |
O2Z—C1Z | 1.201 (4) | C16B—H26 | 0.9600 |
N3A—C12A | 1.480 (4) | C16B—H27 | 0.9600 |
N3A—C13A | 1.483 (4) | C1X—C2X | 1.525 (4) |
N3A—H15 | 0.97 (4) | C2X—C3X | 1.529 (4) |
N3A—H14 | 0.88 (3) | C2X—H5' | 0.9800 |
C12A—C11A | 1.500 (4) | C3X—C3Xii | 1.528 (5) |
C12A—H13 | 0.9700 | C3X—H7' | 0.9800 |
C12A—H12 | 0.9700 | C1Z—C2Z | 1.517 (4) |
C11A—H10 | 0.9700 | C2Z—O3Z | 1.420 (3) |
C11A—H11 | 0.9700 | C2Z—C3Z | 1.530 (4) |
C8A—C9A | 1.385 (4) | C2Z—H11' | 0.9800 |
C8A—C7A | 1.418 (4) | C3Z—C3Ziii | 1.526 (5) |
C9A—C10A | 1.397 (4) | C3Z—H13' | 0.9800 |
C9A—H8 | 0.9300 | O3S—H3A | 0.8500 |
C10A—C5A | 1.408 (4) | O3S—H3B | 0.8498 |
C1A—C2A | 1.369 (4) | O3Z—H10' | 0.8200 |
| | | |
H2B—O2S—H2A | 106 (4) | N2A—C14A—H19 | 109.6 |
C2Y—O3Y—H1' | 109.5 | C13A—C14A—H19 | 109.6 |
C3Y—O4Y—H4Y | 109.5 | N2A—C14A—H18 | 109.6 |
O2Y—C1Y—O1Y | 125.2 (3) | C13A—C14A—H18 | 109.6 |
O2Y—C1Y—C2Y | 117.5 (3) | H19—C14A—H18 | 108.1 |
O1Y—C1Y—C2Y | 117.3 (3) | O1B—C3B—O2B | 120.6 (3) |
O3Y—C2Y—C1Y | 110.5 (2) | O1B—C3B—C2B | 124.3 (4) |
O3Y—C2Y—C3Y | 111.2 (2) | O2B—C3B—C2B | 115.0 (4) |
C1Y—C2Y—C3Y | 111.1 (2) | C1B—C2B—C4B | 120.1 (3) |
O3Y—C2Y—H2' | 108.0 | C1B—C2B—C3B | 117.7 (3) |
C1Y—C2Y—H2' | 108.0 | C4B—C2B—C3B | 122.2 (3) |
C3Y—C2Y—H2' | 108.0 | O3B—C4B—C2B | 122.8 (3) |
O4Y—C3Y—C2Y | 107.2 (2) | O3B—C4B—C5B | 121.6 (3) |
O4Y—C3Y—C3Yi | 110.5 (3) | C2B—C4B—C5B | 115.7 (3) |
C2Y—C3Y—C3Yi | 112.9 (3) | C10B—C5B—C6B | 117.7 (3) |
O4Y—C3Y—H3' | 108.7 | C10B—C5B—C4B | 121.6 (3) |
C2Y—C3Y—H3' | 108.7 | C6B—C5B—C4B | 120.7 (3) |
C3Yi—C3Y—H3' | 108.7 | C7B—C6B—C5B | 120.6 (3) |
C2X—O3X—H6' | 109.5 | C7B—C6B—H21 | 119.7 |
C3X—O4X—H8' | 109.5 | C5B—C6B—H21 | 119.7 |
H1B—O1S—H1A | 109 (4) | C6B—C7B—F1B | 117.3 (3) |
C3A—O2A—H1 | 109.5 | C6B—C7B—C8B | 123.7 (3) |
C3B—O2B—H20 | 109 (2) | F1B—C7B—C8B | 119.0 (3) |
C1Z—O1Z—H9' | 109 (2) | C9B—C8B—N2B | 122.5 (3) |
C3Z—O4Z—H12' | 113 (3) | C9B—C8B—C7B | 115.1 (3) |
C8A—N2A—C14A | 117.4 (3) | N2B—C8B—C7B | 122.3 (3) |
C8A—N2A—C11A | 119.8 (2) | N2B—C11B—C12B | 111.3 (3) |
C14A—N2A—C11A | 109.9 (2) | N2B—C11B—H30 | 109.4 |
C1A—N1A—C10A | 119.7 (3) | C12B—C11B—H30 | 109.4 |
C1A—N1A—C15A | 118.8 (3) | N2B—C11B—H29 | 109.4 |
C10A—N1A—C15A | 121.5 (2) | C12B—C11B—H29 | 109.4 |
C8B—N2B—C11B | 118.1 (2) | H30—C11B—H29 | 108.0 |
C8B—N2B—C14B | 115.1 (2) | N3B—C12B—C11B | 111.0 (3) |
C11B—N2B—C14B | 111.3 (2) | N3B—C12B—H31 | 109.4 |
C13B—N3B—C12B | 110.3 (2) | C11B—C12B—H31 | 109.4 |
C13B—N3B—H34 | 109.6 | N3B—C12B—H32 | 109.4 |
C12B—N3B—H34 | 109.6 | C11B—C12B—H32 | 109.4 |
C13B—N3B—H33 | 109.6 | H31—C12B—H32 | 108.0 |
C12B—N3B—H33 | 109.6 | N1B—C1B—C2B | 124.0 (3) |
H34—N3B—H33 | 108.1 | N1B—C1B—H28 | 118.0 |
C12A—N3A—C13A | 111.5 (2) | C2B—C1B—H28 | 118.0 |
C12A—N3A—H15 | 106 (2) | C1B—N1B—C10B | 120.0 (3) |
C13A—N3A—H15 | 109 (2) | C1B—N1B—C15B | 117.7 (3) |
C12A—N3A—H14 | 110 (2) | C10B—N1B—C15B | 122.3 (2) |
C13A—N3A—H14 | 104 (2) | N1B—C10B—C9B | 121.2 (3) |
H15—N3A—H14 | 116 (3) | N1B—C10B—C5B | 118.6 (3) |
N3A—C12A—C11A | 110.7 (3) | C9B—C10B—C5B | 120.2 (3) |
N3A—C12A—H13 | 109.5 | N3B—C13B—C14B | 112.2 (2) |
C11A—C12A—H13 | 109.5 | N3B—C13B—H36 | 109.2 |
N3A—C12A—H12 | 109.5 | C14B—C13B—H36 | 109.2 |
C11A—C12A—H12 | 109.5 | N3B—C13B—H35 | 109.2 |
H13—C12A—H12 | 108.1 | C14B—C13B—H35 | 109.2 |
N2A—C11A—C12A | 109.1 (3) | H36—C13B—H35 | 107.9 |
N2A—C11A—H10 | 109.9 | N2B—C14B—C13B | 112.1 (3) |
C12A—C11A—H10 | 109.9 | N2B—C14B—H37 | 109.2 |
N2A—C11A—H11 | 109.9 | C13B—C14B—H37 | 109.2 |
C12A—C11A—H11 | 109.9 | N2B—C14B—H38 | 109.2 |
H10—C11A—H11 | 108.3 | C13B—C14B—H38 | 109.2 |
C9A—C8A—N2A | 122.6 (3) | H37—C14B—H38 | 107.9 |
C9A—C8A—C7A | 116.2 (3) | C8B—C9B—C10B | 122.6 (3) |
N2A—C8A—C7A | 121.1 (3) | C8B—C9B—H22 | 118.7 |
C8A—C9A—C10A | 121.9 (3) | C10B—C9B—H22 | 118.7 |
C8A—C9A—H8 | 119.0 | C16B—C15B—N1B | 110.2 (3) |
C10A—C9A—H8 | 119.0 | C16B—C15B—H23 | 109.6 |
N1A—C10A—C9A | 121.4 (3) | N1B—C15B—H23 | 109.6 |
N1A—C10A—C5A | 118.5 (3) | C16B—C15B—H24 | 109.6 |
C9A—C10A—C5A | 120.1 (3) | N1B—C15B—H24 | 109.6 |
N1A—C1A—C2A | 124.2 (3) | H23—C15B—H24 | 108.1 |
N1A—C1A—H2 | 117.9 | C15B—C16B—H25 | 109.5 |
C2A—C1A—H2 | 117.9 | C15B—C16B—H26 | 109.5 |
C1A—C2A—C4A | 120.1 (3) | H25—C16B—H26 | 109.5 |
C1A—C2A—C3A | 118.8 (4) | C15B—C16B—H27 | 109.5 |
C4A—C2A—C3A | 121.1 (3) | H25—C16B—H27 | 109.5 |
O1A—C3A—O2A | 120.9 (3) | H26—C16B—H27 | 109.5 |
O1A—C3A—C2A | 124.7 (4) | O1X—C1X—O2X | 125.5 (3) |
O2A—C3A—C2A | 114.5 (4) | O1X—C1X—C2X | 118.5 (3) |
C16A—C15A—N1A | 111.2 (3) | O2X—C1X—C2X | 116.0 (3) |
C16A—C15A—H4 | 109.4 | O3X—C2X—C1X | 110.2 (2) |
N1A—C15A—H4 | 109.4 | O3X—C2X—C3X | 110.0 (2) |
C16A—C15A—H3 | 109.4 | C1X—C2X—C3X | 112.5 (2) |
N1A—C15A—H3 | 109.4 | O3X—C2X—H5' | 108.0 |
H4—C15A—H3 | 108.0 | C1X—C2X—H5' | 108.0 |
C15A—C16A—H5 | 109.5 | C3X—C2X—H5' | 108.0 |
C15A—C16A—H6 | 109.5 | O4X—C3X—C3Xii | 106.6 (3) |
H5—C16A—H6 | 109.5 | O4X—C3X—C2X | 112.5 (2) |
C15A—C16A—H7 | 109.5 | C3Xii—C3X—C2X | 111.8 (3) |
H5—C16A—H7 | 109.5 | O4X—C3X—H7' | 108.6 |
H6—C16A—H7 | 109.5 | C3Xii—C3X—H7' | 108.6 |
C6A—C5A—C10A | 118.1 (3) | C2X—C3X—H7' | 108.6 |
C6A—C5A—C4A | 120.5 (3) | O2Z—C1Z—O1Z | 125.3 (3) |
C10A—C5A—C4A | 121.4 (3) | O2Z—C1Z—C2Z | 122.7 (3) |
O3A—C4A—C2A | 123.0 (3) | O1Z—C1Z—C2Z | 112.0 (3) |
O3A—C4A—C5A | 121.0 (3) | O3Z—C2Z—C1Z | 109.7 (2) |
C2A—C4A—C5A | 116.0 (3) | O3Z—C2Z—C3Z | 110.2 (2) |
C7A—C6A—C5A | 120.5 (3) | C1Z—C2Z—C3Z | 109.2 (2) |
C7A—C6A—H9 | 119.8 | O3Z—C2Z—H11' | 109.3 |
C5A—C6A—H9 | 119.8 | C1Z—C2Z—H11' | 109.3 |
C6A—C7A—F1A | 118.1 (3) | C3Z—C2Z—H11' | 109.3 |
C6A—C7A—C8A | 123.2 (3) | O4Z—C3Z—C3Ziii | 108.2 (3) |
F1A—C7A—C8A | 118.7 (3) | O4Z—C3Z—C2Z | 108.9 (2) |
N3A—C13A—C14A | 112.3 (3) | C3Ziii—C3Z—C2Z | 111.5 (3) |
N3A—C13A—H16 | 109.1 | O4Z—C3Z—H13' | 109.4 |
C14A—C13A—H16 | 109.1 | C3Ziii—C3Z—H13' | 109.4 |
N3A—C13A—H17 | 109.1 | C2Z—C3Z—H13' | 109.4 |
C14A—C13A—H17 | 109.1 | H3A—O3S—H3B | 107.7 |
H16—C13A—H17 | 107.9 | C2Z—O3Z—H10' | 109.5 |
N2A—C14A—C13A | 110.4 (3) | | |
| | | |
O2Y—C1Y—C2Y—O3Y | 0.2 (4) | C1B—C2B—C4B—O3B | −179.6 (3) |
O1Y—C1Y—C2Y—O3Y | 178.6 (2) | C3B—C2B—C4B—O3B | −1.6 (5) |
O2Y—C1Y—C2Y—C3Y | 124.1 (3) | C1B—C2B—C4B—C5B | 0.4 (4) |
O1Y—C1Y—C2Y—C3Y | −57.5 (3) | C3B—C2B—C4B—C5B | 178.3 (3) |
O3Y—C2Y—C3Y—O4Y | 59.2 (3) | O3B—C4B—C5B—C10B | −178.3 (3) |
C1Y—C2Y—C3Y—O4Y | −64.3 (3) | C2B—C4B—C5B—C10B | 1.7 (4) |
O3Y—C2Y—C3Y—C3Yi | −62.7 (4) | O3B—C4B—C5B—C6B | 4.4 (4) |
C1Y—C2Y—C3Y—C3Yi | 173.8 (3) | C2B—C4B—C5B—C6B | −175.5 (3) |
C13A—N3A—C12A—C11A | 53.8 (4) | C10B—C5B—C6B—C7B | 1.1 (4) |
C8A—N2A—C11A—C12A | −157.1 (3) | C4B—C5B—C6B—C7B | 178.5 (3) |
C14A—N2A—C11A—C12A | 62.6 (3) | C5B—C6B—C7B—F1B | −174.4 (3) |
N3A—C12A—C11A—N2A | −59.5 (3) | C5B—C6B—C7B—C8B | 3.3 (5) |
C14A—N2A—C8A—C9A | 3.2 (4) | C11B—N2B—C8B—C9B | 138.5 (3) |
C11A—N2A—C8A—C9A | −134.3 (3) | C14B—N2B—C8B—C9B | 3.7 (4) |
C14A—N2A—C8A—C7A | −171.8 (3) | C11B—N2B—C8B—C7B | −46.2 (4) |
C11A—N2A—C8A—C7A | 50.7 (4) | C14B—N2B—C8B—C7B | 179.0 (3) |
N2A—C8A—C9A—C10A | −172.2 (3) | C6B—C7B—C8B—C9B | −3.4 (4) |
C7A—C8A—C9A—C10A | 3.0 (4) | F1B—C7B—C8B—C9B | 174.3 (3) |
C1A—N1A—C10A—C9A | −177.2 (3) | C6B—C7B—C8B—N2B | −179.1 (3) |
C15A—N1A—C10A—C9A | 1.6 (4) | F1B—C7B—C8B—N2B | −1.4 (4) |
C1A—N1A—C10A—C5A | 2.7 (4) | C8B—N2B—C11B—C12B | 168.5 (3) |
C15A—N1A—C10A—C5A | −178.5 (3) | C14B—N2B—C11B—C12B | −55.1 (3) |
C8A—C9A—C10A—N1A | 177.3 (3) | C13B—N3B—C12B—C11B | −56.6 (3) |
C8A—C9A—C10A—C5A | −2.6 (4) | N2B—C11B—C12B—N3B | 57.4 (3) |
C10A—N1A—C1A—C2A | −2.5 (5) | C4B—C2B—C1B—N1B | −1.1 (5) |
C15A—N1A—C1A—C2A | 178.8 (3) | C3B—C2B—C1B—N1B | −179.1 (3) |
N1A—C1A—C2A—C4A | 0.4 (5) | C2B—C1B—N1B—C10B | −0.4 (5) |
N1A—C1A—C2A—C3A | −179.1 (3) | C2B—C1B—N1B—C15B | 179.0 (3) |
C1A—C2A—C3A—O1A | −7.1 (5) | C1B—N1B—C10B—C9B | −178.2 (3) |
C4A—C2A—C3A—O1A | 173.4 (3) | C15B—N1B—C10B—C9B | 2.4 (4) |
C1A—C2A—C3A—O2A | 172.1 (3) | C1B—N1B—C10B—C5B | 2.4 (4) |
C4A—C2A—C3A—O2A | −7.4 (4) | C15B—N1B—C10B—C5B | −176.9 (3) |
C1A—N1A—C15A—C16A | 97.1 (3) | C6B—C5B—C10B—N1B | 174.2 (3) |
C10A—N1A—C15A—C16A | −81.7 (4) | C4B—C5B—C10B—N1B | −3.1 (4) |
N1A—C10A—C5A—C6A | −179.7 (3) | C6B—C5B—C10B—C9B | −5.1 (4) |
C9A—C10A—C5A—C6A | 0.2 (4) | C4B—C5B—C10B—C9B | 177.5 (3) |
N1A—C10A—C5A—C4A | −1.0 (4) | C12B—N3B—C13B—C14B | 54.6 (3) |
C9A—C10A—C5A—C4A | 178.9 (3) | C8B—N2B—C14B—C13B | −169.3 (2) |
C1A—C2A—C4A—O3A | −179.7 (3) | C11B—N2B—C14B—C13B | 52.9 (3) |
C3A—C2A—C4A—O3A | −0.3 (5) | N3B—C13B—C14B—N2B | −53.1 (4) |
C1A—C2A—C4A—C5A | 1.3 (4) | N2B—C8B—C9B—C10B | 174.8 (3) |
C3A—C2A—C4A—C5A | −179.2 (3) | C7B—C8B—C9B—C10B | −0.8 (4) |
C6A—C5A—C4A—O3A | −1.3 (4) | N1B—C10B—C9B—C8B | −174.2 (3) |
C10A—C5A—C4A—O3A | −180.0 (3) | C5B—C10B—C9B—C8B | 5.1 (4) |
C6A—C5A—C4A—C2A | 177.7 (3) | C1B—N1B—C15B—C16B | 90.9 (4) |
C10A—C5A—C4A—C2A | −1.0 (4) | C10B—N1B—C15B—C16B | −89.7 (4) |
C10A—C5A—C6A—C7A | 1.7 (4) | O1X—C1X—C2X—O3X | −175.2 (2) |
C4A—C5A—C6A—C7A | −177.0 (3) | O2X—C1X—C2X—O3X | 5.1 (4) |
C5A—C6A—C7A—F1A | 175.3 (3) | O1X—C1X—C2X—C3X | 61.5 (4) |
C5A—C6A—C7A—C8A | −1.3 (5) | O2X—C1X—C2X—C3X | −118.1 (3) |
C9A—C8A—C7A—C6A | −1.0 (4) | O3X—C2X—C3X—O4X | −70.2 (3) |
N2A—C8A—C7A—C6A | 174.2 (3) | C1X—C2X—C3X—O4X | 53.1 (3) |
C9A—C8A—C7A—F1A | −177.6 (2) | O3X—C2X—C3X—C3Xii | 49.7 (4) |
N2A—C8A—C7A—F1A | −2.3 (4) | C1X—C2X—C3X—C3Xii | 173.0 (3) |
C12A—N3A—C13A—C14A | −50.9 (4) | O2Z—C1Z—C2Z—O3Z | −16.4 (4) |
C8A—N2A—C14A—C13A | 159.1 (3) | O1Z—C1Z—C2Z—O3Z | 165.8 (3) |
C11A—N2A—C14A—C13A | −59.5 (3) | O2Z—C1Z—C2Z—C3Z | 104.4 (4) |
N3A—C13A—C14A—N2A | 53.7 (3) | O1Z—C1Z—C2Z—C3Z | −73.4 (3) |
O1B—C3B—C2B—C1B | 3.0 (5) | O3Z—C2Z—C3Z—O4Z | 52.1 (3) |
O2B—C3B—C2B—C1B | −177.3 (3) | C1Z—C2Z—C3Z—O4Z | −68.3 (3) |
O1B—C3B—C2B—C4B | −175.0 (4) | O3Z—C2Z—C3Z—C3Ziii | −67.2 (4) |
O2B—C3B—C2B—C4B | 4.7 (5) | C1Z—C2Z—C3Z—C3Ziii | 172.3 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y, −z+1; (iii) −x+1, −y+1, −z+1. |
Crystal data top
C23H26FN3O7 | Z = 4 |
Mr = 475.47 | F(000) = 1000 |
Monoclinic, P21/c | Dx = 1.434 Mg m−3 |
a = 8.0761 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.7184 (3) Å | µ = 0.11 mm−1 |
c = 18.7770 (4) Å | T = 100 K |
β = 99.269 (1)° | Block, colorless |
V = 2202.83 (8) Å3 | 0.42 × 0.32 × 0.21 mm |
Data collection top
CCD area detector diffractometer | 3253 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 25.0°, θmin = 1.8° |
phi and ω scans | h = −9→9 |
31912 measured reflections | k = −17→17 |
3883 independent reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H 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 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.25 e Å−3 |
Crystal data top
C23H26FN3O7 | V = 2202.83 (8) Å3 |
Mr = 475.47 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.0761 (2) Å | µ = 0.11 mm−1 |
b = 14.7184 (3) Å | T = 100 K |
c = 18.7770 (4) Å | 0.42 × 0.32 × 0.21 mm |
β = 99.269 (1)° | |
Data collection top
CCD area detector diffractometer | 3253 reflections with I > 2σ(I) |
31912 measured reflections | Rint = 0.034 |
3883 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.033 | 0 restraints |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | Δρmax = 0.21 e Å−3 |
3883 reflections | Δρmin = −0.25 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
F1 | 0.42326 (10) | 0.81417 (6) | 0.38762 (4) | 0.0202 (2) | |
O2 | −0.20034 (17) | 0.83988 (10) | 0.64181 (6) | 0.0432 (4) | |
H1 | −0.100 (3) | 0.8235 (16) | 0.6309 (13) | 0.065* | |
O1 | −0.42529 (15) | 0.91128 (9) | 0.58481 (6) | 0.0378 (3) | |
O3 | 0.04864 (13) | 0.81039 (7) | 0.57741 (5) | 0.0233 (3) | |
N3 | 0.30604 (16) | 0.83197 (8) | 0.11748 (7) | 0.0169 (3) | |
O2' | 0.53093 (12) | 0.84794 (7) | 1.02601 (5) | 0.0226 (3) | |
O1' | 0.38449 (12) | 0.88257 (7) | 0.91781 (6) | 0.0233 (3) | |
O3' | 1.12728 (13) | 0.87721 (8) | 0.98336 (6) | 0.0241 (3) | |
H3' | 1.215 (2) | 0.8799 (12) | 0.9569 (10) | 0.036* | |
O1S | 0.30291 (15) | 0.44256 (9) | 0.34929 (6) | 0.0296 (3) | |
H1B | 0.333 (3) | 0.4109 (14) | 0.3878 (11) | 0.044* | |
H1A | 0.328 (3) | 0.4978 (15) | 0.3654 (11) | 0.044* | |
N2 | 0.23123 (15) | 0.86103 (8) | 0.25962 (6) | 0.0164 (3) | |
N1 | −0.22735 (15) | 0.91939 (8) | 0.39439 (6) | 0.0166 (3) | |
C12 | 0.39814 (18) | 0.78183 (10) | 0.18061 (7) | 0.0174 (3) | |
H12 | 0.4989 | 0.8149 | 0.2005 | 0.021* | |
H13 | 0.4311 | 0.7224 | 0.1654 | 0.021* | |
C3 | −0.2865 (2) | 0.88043 (12) | 0.58381 (9) | 0.0292 (4) | |
C2 | −0.19933 (19) | 0.88385 (10) | 0.52005 (8) | 0.0201 (3) | |
C4 | −0.03410 (19) | 0.84825 (10) | 0.52170 (8) | 0.0186 (3) | |
C5 | 0.03497 (18) | 0.85737 (9) | 0.45542 (7) | 0.0164 (3) | |
C6 | 0.20201 (18) | 0.83173 (10) | 0.45275 (8) | 0.0172 (3) | |
H9 | 0.2718 | 0.8128 | 0.4944 | 0.021* | |
C7 | 0.25997 (17) | 0.83500 (9) | 0.38897 (8) | 0.0165 (3) | |
C8 | 0.16021 (18) | 0.86086 (9) | 0.32319 (7) | 0.0155 (3) | |
C14 | 0.13694 (19) | 0.90895 (10) | 0.19760 (8) | 0.0199 (3) | |
H2' | 0.1004 | 0.9676 | 0.2128 | 0.024* | |
H1' | 0.0383 | 0.8741 | 0.1778 | 0.024* | |
C13 | 0.2475 (2) | 0.92176 (10) | 0.14082 (8) | 0.0202 (3) | |
H17 | 0.1854 | 0.9532 | 0.0996 | 0.024* | |
H16 | 0.3437 | 0.9588 | 0.1601 | 0.024* | |
C10 | −0.06431 (18) | 0.88930 (9) | 0.39175 (8) | 0.0158 (3) | |
C1 | −0.28645 (19) | 0.91834 (10) | 0.45688 (8) | 0.0186 (3) | |
H2 | −0.3927 | 0.9423 | 0.4577 | 0.022* | |
C15 | −0.33573 (18) | 0.95418 (10) | 0.32862 (8) | 0.0182 (3) | |
H3 | −0.4511 | 0.9562 | 0.3370 | 0.022* | |
H4 | −0.3304 | 0.9126 | 0.2890 | 0.022* | |
C16 | −0.2840 (2) | 1.04770 (10) | 0.30770 (8) | 0.0241 (4) | |
H5 | −0.2821 | 1.0883 | 0.3478 | 0.036* | |
H7 | −0.3628 | 1.0695 | 0.2675 | 0.036* | |
H6 | −0.1742 | 1.0448 | 0.2944 | 0.036* | |
C9 | −0.00224 (18) | 0.88868 (9) | 0.32601 (8) | 0.0163 (3) | |
H8 | −0.0711 | 0.9072 | 0.2840 | 0.020* | |
C11 | 0.28642 (18) | 0.77126 (10) | 0.23757 (8) | 0.0172 (3) | |
H11 | 0.1892 | 0.7349 | 0.2185 | 0.021* | |
H10 | 0.3474 | 0.7400 | 0.2792 | 0.021* | |
C7' | 0.51952 (18) | 0.86369 (10) | 0.95935 (8) | 0.0175 (3) | |
C1' | 0.67732 (18) | 0.85957 (9) | 0.92638 (8) | 0.0164 (3) | |
C2' | 0.83346 (18) | 0.86716 (10) | 0.96962 (8) | 0.0169 (3) | |
H4' | 0.8407 | 0.8720 | 1.0194 | 0.020* | |
C3' | 0.97903 (17) | 0.86753 (10) | 0.93876 (8) | 0.0168 (3) | |
C4' | 0.96881 (18) | 0.85723 (10) | 0.86446 (8) | 0.0178 (3) | |
H7' | 1.0659 | 0.8567 | 0.8437 | 0.021* | |
C5' | 0.81307 (19) | 0.84775 (10) | 0.82154 (8) | 0.0201 (3) | |
H6' | 0.8060 | 0.8398 | 0.7720 | 0.024* | |
C6' | 0.66806 (18) | 0.85010 (10) | 0.85203 (8) | 0.0194 (3) | |
H5' | 0.5640 | 0.8453 | 0.8227 | 0.023* | |
H14 | 0.380 (2) | 0.8405 (12) | 0.0816 (10) | 0.037 (5)* | |
H15 | 0.211 (2) | 0.7988 (12) | 0.0961 (10) | 0.032 (5)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0133 (4) | 0.0278 (5) | 0.0200 (4) | 0.0019 (3) | 0.0040 (3) | 0.0019 (4) |
O2 | 0.0363 (8) | 0.0793 (10) | 0.0165 (6) | 0.0269 (7) | 0.0117 (6) | 0.0132 (6) |
O1 | 0.0320 (7) | 0.0593 (8) | 0.0255 (7) | 0.0200 (6) | 0.0146 (5) | 0.0078 (6) |
O3 | 0.0225 (6) | 0.0353 (6) | 0.0120 (5) | 0.0082 (5) | 0.0023 (4) | 0.0025 (4) |
N3 | 0.0156 (7) | 0.0215 (7) | 0.0146 (6) | −0.0002 (5) | 0.0048 (5) | −0.0003 (5) |
O2' | 0.0175 (6) | 0.0330 (6) | 0.0189 (6) | −0.0016 (5) | 0.0072 (4) | 0.0001 (5) |
O1' | 0.0119 (5) | 0.0315 (6) | 0.0265 (6) | 0.0008 (4) | 0.0033 (5) | 0.0031 (5) |
O3' | 0.0099 (5) | 0.0434 (7) | 0.0186 (6) | −0.0002 (5) | 0.0016 (5) | 0.0010 (5) |
O1S | 0.0340 (7) | 0.0324 (7) | 0.0220 (6) | 0.0021 (5) | 0.0031 (5) | −0.0001 (5) |
N2 | 0.0181 (6) | 0.0181 (6) | 0.0138 (6) | 0.0031 (5) | 0.0052 (5) | 0.0019 (5) |
N1 | 0.0163 (6) | 0.0195 (6) | 0.0143 (6) | 0.0017 (5) | 0.0033 (5) | 0.0001 (5) |
C12 | 0.0159 (7) | 0.0191 (7) | 0.0172 (7) | 0.0020 (6) | 0.0029 (6) | −0.0005 (6) |
C3 | 0.0283 (9) | 0.0421 (10) | 0.0182 (8) | 0.0103 (8) | 0.0070 (7) | 0.0025 (7) |
C2 | 0.0209 (8) | 0.0254 (8) | 0.0150 (7) | 0.0038 (6) | 0.0054 (6) | −0.0014 (6) |
C4 | 0.0208 (8) | 0.0210 (7) | 0.0137 (7) | 0.0004 (6) | 0.0020 (6) | −0.0025 (6) |
C5 | 0.0179 (8) | 0.0170 (7) | 0.0143 (7) | −0.0002 (6) | 0.0024 (6) | −0.0011 (6) |
C6 | 0.0172 (8) | 0.0192 (7) | 0.0143 (7) | 0.0008 (6) | −0.0004 (6) | 0.0009 (6) |
C7 | 0.0121 (7) | 0.0176 (7) | 0.0204 (8) | −0.0002 (6) | 0.0044 (6) | −0.0011 (6) |
C8 | 0.0175 (8) | 0.0139 (7) | 0.0158 (7) | −0.0015 (6) | 0.0043 (6) | 0.0007 (6) |
C14 | 0.0210 (8) | 0.0215 (8) | 0.0181 (8) | 0.0058 (6) | 0.0059 (6) | 0.0038 (6) |
C13 | 0.0239 (8) | 0.0199 (8) | 0.0180 (8) | 0.0036 (6) | 0.0066 (6) | 0.0028 (6) |
C10 | 0.0164 (7) | 0.0142 (7) | 0.0170 (7) | −0.0003 (6) | 0.0036 (6) | −0.0015 (6) |
C1 | 0.0183 (8) | 0.0208 (8) | 0.0178 (8) | 0.0024 (6) | 0.0062 (6) | −0.0021 (6) |
C15 | 0.0163 (8) | 0.0233 (8) | 0.0147 (7) | 0.0034 (6) | 0.0018 (6) | 0.0012 (6) |
C16 | 0.0268 (9) | 0.0229 (8) | 0.0229 (8) | 0.0053 (7) | 0.0048 (7) | 0.0028 (6) |
C9 | 0.0182 (8) | 0.0164 (7) | 0.0141 (7) | 0.0007 (6) | 0.0014 (6) | 0.0010 (6) |
C11 | 0.0180 (8) | 0.0174 (7) | 0.0162 (7) | 0.0025 (6) | 0.0030 (6) | 0.0006 (6) |
C7' | 0.0142 (8) | 0.0177 (7) | 0.0206 (8) | −0.0020 (6) | 0.0028 (6) | −0.0006 (6) |
C1' | 0.0144 (7) | 0.0162 (7) | 0.0187 (8) | −0.0006 (6) | 0.0032 (6) | 0.0023 (6) |
C2' | 0.0166 (8) | 0.0215 (8) | 0.0130 (7) | 0.0011 (6) | 0.0041 (6) | 0.0019 (6) |
C3' | 0.0120 (7) | 0.0189 (7) | 0.0187 (7) | 0.0010 (6) | 0.0004 (6) | 0.0017 (6) |
C4' | 0.0143 (7) | 0.0211 (8) | 0.0198 (8) | 0.0010 (6) | 0.0082 (6) | 0.0016 (6) |
C5' | 0.0221 (8) | 0.0244 (8) | 0.0143 (7) | −0.0017 (6) | 0.0043 (6) | −0.0010 (6) |
C6' | 0.0143 (8) | 0.0240 (8) | 0.0191 (8) | −0.0035 (6) | 0.0003 (6) | −0.0001 (6) |
Geometric parameters (Å, º) top
F1—C7 | 1.3580 (16) | C6—H9 | 0.9300 |
O2—C3 | 1.335 (2) | C7—C8 | 1.414 (2) |
O2—H1 | 0.90 (3) | C8—C9 | 1.384 (2) |
O1—C3 | 1.212 (2) | C14—C13 | 1.509 (2) |
O3—C4 | 1.2752 (18) | C14—H2' | 0.9700 |
N3—C12 | 1.4896 (18) | C14—H1' | 0.9700 |
N3—C13 | 1.4928 (18) | C13—H17 | 0.9700 |
N3—H14 | 0.98 (2) | C13—H16 | 0.9700 |
N3—H15 | 0.940 (19) | C10—C9 | 1.405 (2) |
O2'—C7' | 1.2616 (17) | C1—H2 | 0.9300 |
O1'—C7' | 1.2653 (17) | C15—C16 | 1.509 (2) |
O3'—C3' | 1.3535 (17) | C15—H3 | 0.9700 |
O3'—H3' | 0.93 (2) | C15—H4 | 0.9700 |
O1S—H1B | 0.86 (2) | C16—H5 | 0.9600 |
O1S—H1A | 0.88 (2) | C16—H7 | 0.9600 |
N2—C8 | 1.4050 (18) | C16—H6 | 0.9600 |
N2—C14 | 1.4655 (18) | C9—H8 | 0.9300 |
N2—C11 | 1.4749 (18) | C11—H11 | 0.9700 |
N1—C1 | 1.3361 (18) | C11—H10 | 0.9700 |
N1—C10 | 1.3976 (18) | C7'—C1' | 1.505 (2) |
N1—C15 | 1.4850 (18) | C1'—C2' | 1.390 (2) |
C12—C11 | 1.5142 (19) | C1'—C6' | 1.393 (2) |
C12—H12 | 0.9700 | C2'—C3' | 1.392 (2) |
C12—H13 | 0.9700 | C2'—H4' | 0.9300 |
C3—C2 | 1.484 (2) | C3'—C4' | 1.393 (2) |
C2—C1 | 1.375 (2) | C4'—C5' | 1.387 (2) |
C2—C4 | 1.429 (2) | C4'—H7' | 0.9300 |
C4—C5 | 1.450 (2) | C5'—C6' | 1.384 (2) |
C5—C10 | 1.409 (2) | C5'—H6' | 0.9300 |
C5—C6 | 1.409 (2) | C6'—H5' | 0.9300 |
C6—C7 | 1.355 (2) | | |
| | | |
C3—O2—H1 | 107.8 (15) | N3—C13—H16 | 109.6 |
C12—N3—C13 | 110.25 (11) | C14—C13—H16 | 109.6 |
C12—N3—H14 | 109.4 (11) | H17—C13—H16 | 108.1 |
C13—N3—H14 | 110.2 (11) | N1—C10—C9 | 120.31 (13) |
C12—N3—H15 | 110.5 (11) | N1—C10—C5 | 119.10 (12) |
C13—N3—H15 | 108.1 (11) | C9—C10—C5 | 120.57 (13) |
H14—N3—H15 | 108.5 (15) | N1—C1—C2 | 123.81 (14) |
C3'—O3'—H3' | 110.4 (11) | N1—C1—H2 | 118.1 |
H1B—O1S—H1A | 101.2 (19) | C2—C1—H2 | 118.1 |
C8—N2—C14 | 116.42 (11) | N1—C15—C16 | 112.35 (12) |
C8—N2—C11 | 114.84 (11) | N1—C15—H3 | 109.1 |
C14—N2—C11 | 110.47 (11) | C16—C15—H3 | 109.1 |
C1—N1—C10 | 119.96 (12) | N1—C15—H4 | 109.1 |
C1—N1—C15 | 119.22 (12) | C16—C15—H4 | 109.1 |
C10—N1—C15 | 120.81 (11) | H3—C15—H4 | 107.9 |
N3—C12—C11 | 109.57 (11) | C15—C16—H5 | 109.5 |
N3—C12—H12 | 109.8 | C15—C16—H7 | 109.5 |
C11—C12—H12 | 109.8 | H5—C16—H7 | 109.5 |
N3—C12—H13 | 109.8 | C15—C16—H6 | 109.5 |
C11—C12—H13 | 109.8 | H5—C16—H6 | 109.5 |
H12—C12—H13 | 108.2 | H7—C16—H6 | 109.5 |
O1—C3—O2 | 121.10 (15) | C8—C9—C10 | 120.68 (13) |
O1—C3—C2 | 124.02 (15) | C8—C9—H8 | 119.7 |
O2—C3—C2 | 114.87 (14) | C10—C9—H8 | 119.7 |
C1—C2—C4 | 120.00 (13) | N2—C11—C12 | 110.35 (11) |
C1—C2—C3 | 117.72 (14) | N2—C11—H11 | 109.6 |
C4—C2—C3 | 122.18 (13) | C12—C11—H11 | 109.6 |
O3—C4—C2 | 122.81 (13) | N2—C11—H10 | 109.6 |
O3—C4—C5 | 121.43 (13) | C12—C11—H10 | 109.6 |
C2—C4—C5 | 115.76 (13) | H11—C11—H10 | 108.1 |
C10—C5—C6 | 118.44 (13) | O2'—C7'—O1' | 124.75 (13) |
C10—C5—C4 | 120.95 (13) | O2'—C7'—C1' | 117.99 (13) |
C6—C5—C4 | 120.57 (13) | O1'—C7'—C1' | 117.26 (12) |
C7—C6—C5 | 119.39 (13) | C2'—C1'—C6' | 119.39 (13) |
C7—C6—H9 | 120.3 | C2'—C1'—C7' | 120.33 (13) |
C5—C6—H9 | 120.3 | C6'—C1'—C7' | 120.26 (13) |
C6—C7—F1 | 118.89 (13) | C1'—C2'—C3' | 120.31 (13) |
C6—C7—C8 | 123.52 (13) | C1'—C2'—H4' | 119.8 |
F1—C7—C8 | 117.58 (12) | C3'—C2'—H4' | 119.8 |
C9—C8—N2 | 123.46 (13) | O3'—C3'—C2' | 117.71 (13) |
C9—C8—C7 | 117.17 (13) | O3'—C3'—C4' | 122.36 (13) |
N2—C8—C7 | 119.31 (12) | C2'—C3'—C4' | 119.93 (13) |
N2—C14—C13 | 109.32 (12) | C5'—C4'—C3' | 119.66 (13) |
N2—C14—H2' | 109.8 | C5'—C4'—H7' | 120.2 |
C13—C14—H2' | 109.8 | C3'—C4'—H7' | 120.2 |
N2—C14—H1' | 109.8 | C6'—C5'—C4' | 120.37 (14) |
C13—C14—H1' | 109.8 | C6'—C5'—H6' | 119.8 |
H2'—C14—H1' | 108.3 | C4'—C5'—H6' | 119.8 |
N3—C13—C14 | 110.38 (12) | C5'—C6'—C1' | 120.30 (14) |
N3—C13—H17 | 109.6 | C5'—C6'—H5' | 119.9 |
C14—C13—H17 | 109.6 | C1'—C6'—H5' | 119.9 |
| | | |
C13—N3—C12—C11 | 56.71 (15) | C15—N1—C10—C5 | 179.56 (12) |
O1—C3—C2—C1 | −4.8 (3) | C6—C5—C10—N1 | −176.72 (13) |
O2—C3—C2—C1 | 175.03 (15) | C4—C5—C10—N1 | 5.2 (2) |
O1—C3—C2—C4 | 178.68 (17) | C6—C5—C10—C9 | 5.0 (2) |
O2—C3—C2—C4 | −1.5 (2) | C4—C5—C10—C9 | −173.08 (13) |
C1—C2—C4—O3 | −175.59 (14) | C10—N1—C1—C2 | −4.0 (2) |
C3—C2—C4—O3 | 0.8 (2) | C15—N1—C1—C2 | 176.99 (14) |
C1—C2—C4—C5 | 4.2 (2) | C4—C2—C1—N1 | 1.5 (2) |
C3—C2—C4—C5 | −179.43 (14) | C3—C2—C1—N1 | −175.11 (14) |
O3—C4—C5—C10 | 172.34 (13) | C1—N1—C15—C16 | 104.83 (15) |
C2—C4—C5—C10 | −7.4 (2) | C10—N1—C15—C16 | −74.17 (16) |
O3—C4—C5—C6 | −5.7 (2) | N2—C8—C9—C10 | −178.18 (13) |
C2—C4—C5—C6 | 174.56 (13) | C7—C8—C9—C10 | −1.1 (2) |
C10—C5—C6—C7 | −2.6 (2) | N1—C10—C9—C8 | 178.59 (13) |
C4—C5—C6—C7 | 175.46 (13) | C5—C10—C9—C8 | −3.1 (2) |
C5—C6—C7—F1 | 177.00 (12) | C8—N2—C11—C12 | −165.92 (12) |
C5—C6—C7—C8 | −1.7 (2) | C14—N2—C11—C12 | 59.95 (15) |
C14—N2—C8—C9 | 11.58 (19) | N3—C12—C11—N2 | −57.74 (15) |
C11—N2—C8—C9 | −119.75 (15) | O2'—C7'—C1'—C2' | −20.0 (2) |
C14—N2—C8—C7 | −165.48 (13) | O1'—C7'—C1'—C2' | 160.21 (13) |
C11—N2—C8—C7 | 63.19 (17) | O2'—C7'—C1'—C6' | 161.42 (13) |
C6—C7—C8—C9 | 3.5 (2) | O1'—C7'—C1'—C6' | −18.4 (2) |
F1—C7—C8—C9 | −175.15 (12) | C6'—C1'—C2'—C3' | 1.6 (2) |
C6—C7—C8—N2 | −179.21 (13) | C7'—C1'—C2'—C3' | −177.04 (13) |
F1—C7—C8—N2 | 2.10 (19) | C1'—C2'—C3'—O3' | 178.50 (13) |
C8—N2—C14—C13 | 166.68 (12) | C1'—C2'—C3'—C4' | −2.1 (2) |
C11—N2—C14—C13 | −59.99 (15) | O3'—C3'—C4'—C5' | −179.89 (13) |
C12—N3—C13—C14 | −57.83 (16) | C2'—C3'—C4'—C5' | 0.8 (2) |
N2—C14—C13—N3 | 58.93 (16) | C3'—C4'—C5'—C6' | 1.1 (2) |
C1—N1—C10—C9 | 178.87 (13) | C4'—C5'—C6'—C1' | −1.7 (2) |
C15—N1—C10—C9 | −2.1 (2) | C2'—C1'—C6'—C5' | 0.4 (2) |
C1—N1—C10—C5 | 0.6 (2) | C7'—C1'—C6'—C5' | 178.97 (13) |
Crystal data top
C21H30FN3O10S | V = 1155.6 (5) Å3 |
Mr = 535.55 | Z = 2 |
Triclinic, P1 | F(000) = 564.0 |
a = 9.041 (3) Å | Dx = 1.539 Mg m−3 |
b = 10.767 (3) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 12.438 (3) Å | µ = 0.21 mm−1 |
α = 89.118 (19)° | T = 100 K |
β = 81.880 (17)° | Sheet, colorless |
γ = 74.64 (2)° | 0.21 × 0.15 × 0.13 mm |
Data collection top
CCD area detector diffractometer | 2459 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.101 |
Graphite monochromator | θmax = 25.0°, θmin = 1.7° |
phi and ω scans | h = −10→10 |
15891 measured reflections | k = −12→12 |
4065 independent reflections | l = −14→14 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H 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 parameters | Δρmax = 0.41 e Å−3 |
22 restraints | Δρmin = −0.41 e Å−3 |
Crystal data top
C21H30FN3O10S | γ = 74.64 (2)° |
Mr = 535.55 | V = 1155.6 (5) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.041 (3) Å | Mo Kα radiation |
b = 10.767 (3) Å | µ = 0.21 mm−1 |
c = 12.438 (3) Å | T = 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 reflections | Rint = 0.101 |
4065 independent reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.047 | 22 restraints |
wR(F2) = 0.075 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.41 e Å−3 |
4065 reflections | Δρmin = −0.41 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
O1' | 0.6998 (2) | 0.00961 (19) | 0.80804 (15) | 0.0173 (5) | |
S1 | 0.78173 (9) | 0.11106 (8) | 0.79393 (6) | 0.0144 (2) | |
F1 | −0.36051 (18) | 0.45642 (16) | 0.13590 (12) | 0.0165 (4) | |
O1S | 0.3659 (2) | 0.57997 (19) | 0.32050 (15) | 0.0199 (5) | |
H1A | 0.3302 | 0.6133 | 0.2687 | 0.030* | |
H1B | 0.4513 | 0.5975 | 0.3234 | 0.030* | |
O4S | 0.6974 (2) | 0.01821 (19) | 0.45137 (16) | 0.0250 (6) | |
H4B | 0.6200 | 0.0198 | 0.4127 | 0.038* | |
H4A | 0.6776 | −0.0148 | 0.5102 | 0.038* | |
O1 | 0.3801 (2) | 0.3448 (2) | −0.36931 (16) | 0.0207 (5) | |
N3 | −0.2310 (3) | 0.2514 (3) | 0.4917 (2) | 0.0167 (7) | |
O2 | 0.1325 (2) | 0.40459 (19) | −0.39447 (15) | 0.0189 (5) | |
H1 | 0.0475 | 0.4118 | −0.3581 | 0.028* | |
O3 | −0.0763 (2) | 0.43031 (19) | −0.24066 (15) | 0.0166 (5) | |
O3' | 0.8437 (2) | 0.12433 (19) | 0.68129 (15) | 0.0166 (5) | |
O2' | 0.6884 (2) | 0.23205 (19) | 0.84730 (15) | 0.0163 (5) | |
C3 | 0.2410 (4) | 0.3633 (3) | −0.3335 (2) | 0.0164 (7) | |
C2 | 0.1857 (3) | 0.3414 (3) | −0.2191 (2) | 0.0116 (7) | |
C4 | 0.0253 (4) | 0.3795 (3) | −0.1784 (2) | 0.0130 (7) | |
C5 | −0.0191 (3) | 0.3617 (3) | −0.0657 (2) | 0.0106 (7) | |
C6 | −0.1745 (3) | 0.4073 (3) | −0.0164 (2) | 0.0122 (8) | |
H9 | −0.2512 | 0.4451 | −0.0583 | 0.015* | |
C7 | −0.2115 (3) | 0.3960 (3) | 0.0913 (2) | 0.0112 (7) | |
C8 | −0.1063 (4) | 0.3290 (3) | 0.1600 (2) | 0.0112 (7) | |
C14 | −0.0290 (3) | 0.2480 (3) | 0.3339 (2) | 0.0154 (8) | |
H18 | 0.0660 | 0.2729 | 0.3110 | 0.019* | |
H19 | −0.0084 | 0.1564 | 0.3192 | 0.019* | |
C13 | −0.0766 (3) | 0.2745 (3) | 0.4540 (2) | 0.0182 (8) | |
H16 | 0.0004 | 0.2193 | 0.4930 | 0.022* | |
H17 | −0.0807 | 0.3632 | 0.4703 | 0.022* | |
C11 | −0.3004 (3) | 0.2924 (3) | 0.3099 (2) | 0.0152 (8) | |
H11 | −0.2919 | 0.2015 | 0.2995 | 0.018* | |
H10 | −0.3781 | 0.3410 | 0.2679 | 0.018* | |
C12 | −0.3499 (3) | 0.3293 (3) | 0.4284 (2) | 0.0160 (8) | |
H13 | −0.3598 | 0.4203 | 0.4392 | 0.019* | |
H12 | −0.4496 | 0.3131 | 0.4528 | 0.019* | |
C10 | 0.0917 (3) | 0.3018 (3) | 0.0005 (2) | 0.0122 (7) | |
C9 | 0.0478 (3) | 0.2815 (3) | 0.1100 (2) | 0.0116 (7) | |
H8 | 0.1221 | 0.2357 | 0.1507 | 0.014* | |
N1 | 0.2482 (3) | 0.2619 (2) | −0.04663 (19) | 0.0110 (6) | |
C1 | 0.2894 (4) | 0.2845 (3) | −0.1512 (2) | 0.0128 (8) | |
H2 | 0.3941 | 0.2601 | −0.1792 | 0.015* | |
C3' | 0.9470 (3) | 0.0563 (3) | 0.8637 (2) | 0.0101 (7) | |
C2' | 0.9315 (3) | 0.0256 (3) | 0.9761 (2) | 0.0105 (7) | |
C4' | 1.0910 (3) | 0.0414 (3) | 0.8043 (2) | 0.0132 (8) | |
H4' | 1.0994 | 0.0641 | 0.7317 | 0.016* | |
C5' | 1.2258 (4) | −0.0081 (3) | 0.8525 (2) | 0.0152 (8) | |
H5' | 1.3228 | −0.0176 | 0.8118 | 0.018* | |
C1' | 0.7855 (3) | 0.0421 (3) | 1.0410 (2) | 0.0145 (8) | |
H1' | 0.6956 | 0.0768 | 1.0106 | 0.017* | |
O3S | 0.4143 (2) | 0.0952 (2) | 0.35731 (15) | 0.0240 (6) | |
H3B | 0.3684 | 0.1716 | 0.3609 | 0.036* | |
H3A | 0.3828 | 0.0619 | 0.3051 | 0.036* | |
N2 | −0.1494 (3) | 0.3186 (2) | 0.27087 (18) | 0.0119 (6) | |
O2S | 0.2716 (2) | 0.35555 (19) | 0.38184 (15) | 0.0211 (6) | |
H2A | 0.2358 | 0.3723 | 0.4528 | 0.032* | |
H2B | 0.3046 | 0.4159 | 0.3567 | 0.032* | |
C15 | 0.3703 (3) | 0.1960 (3) | 0.0180 (2) | 0.0142 (8) | |
H3 | 0.4600 | 0.1482 | −0.0308 | 0.017* | |
H4 | 0.3325 | 0.1348 | 0.0647 | 0.017* | |
C16 | 0.4194 (3) | 0.2887 (3) | 0.0875 (2) | 0.0188 (8) | |
H7 | 0.4662 | 0.3443 | 0.0413 | 0.028* | |
H6 | 0.4928 | 0.2408 | 0.1317 | 0.028* | |
H5 | 0.3301 | 0.3396 | 0.1333 | 0.028* | |
H14 | −0.257 (3) | 0.274 (3) | 0.5600 (7) | 0.032 (11)* | |
H15 | −0.238 (4) | 0.162 (3) | 0.487 (3) | 0.057 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1' | 0.0207 (12) | 0.0185 (12) | 0.0179 (12) | −0.0105 (9) | −0.0102 (10) | 0.0023 (9) |
S1 | 0.0150 (5) | 0.0159 (5) | 0.0137 (5) | −0.0049 (4) | −0.0055 (4) | 0.0011 (4) |
F1 | 0.0093 (10) | 0.0216 (11) | 0.0165 (10) | −0.0015 (8) | 0.0002 (8) | −0.0019 (8) |
O1S | 0.0171 (13) | 0.0242 (14) | 0.0198 (13) | −0.0055 (11) | −0.0080 (10) | 0.0040 (10) |
O4S | 0.0266 (14) | 0.0315 (15) | 0.0212 (14) | −0.0145 (12) | −0.0044 (11) | 0.0035 (11) |
O1 | 0.0190 (11) | 0.0300 (14) | 0.0149 (13) | −0.0111 (12) | 0.0004 (10) | 0.0004 (10) |
N3 | 0.0154 (17) | 0.024 (2) | 0.0123 (18) | −0.0065 (14) | −0.0035 (14) | 0.0014 (14) |
O2 | 0.0134 (13) | 0.0323 (15) | 0.0135 (13) | −0.0107 (11) | −0.0013 (10) | 0.0035 (10) |
O3 | 0.0141 (12) | 0.0211 (13) | 0.0164 (12) | −0.0056 (10) | −0.0063 (9) | 0.0019 (9) |
O3' | 0.0169 (13) | 0.0236 (14) | 0.0084 (12) | −0.0035 (10) | −0.0033 (10) | 0.0050 (10) |
O2' | 0.0126 (12) | 0.0157 (13) | 0.0185 (13) | 0.0006 (10) | −0.0033 (10) | −0.0028 (10) |
C3 | 0.0192 (13) | 0.0178 (18) | 0.0151 (18) | −0.0098 (16) | −0.0028 (15) | −0.0028 (14) |
C2 | 0.0124 (19) | 0.0116 (19) | 0.0123 (19) | −0.0059 (15) | −0.0010 (15) | −0.0017 (14) |
C4 | 0.0152 (17) | 0.0130 (18) | 0.0146 (18) | −0.0081 (13) | −0.0061 (12) | −0.0012 (13) |
C5 | 0.0105 (18) | 0.0095 (19) | 0.0122 (18) | −0.0016 (14) | −0.0043 (15) | −0.0003 (14) |
C6 | 0.0134 (19) | 0.0114 (19) | 0.0143 (19) | −0.0046 (15) | −0.0074 (15) | −0.0006 (14) |
C7 | 0.0044 (18) | 0.0101 (19) | 0.018 (2) | −0.0013 (14) | 0.0002 (15) | −0.0045 (14) |
C8 | 0.0155 (19) | 0.0096 (19) | 0.0111 (19) | −0.0065 (15) | −0.0042 (15) | −0.0030 (14) |
C14 | 0.0125 (18) | 0.020 (2) | 0.0138 (19) | −0.0032 (16) | −0.0052 (15) | 0.0003 (15) |
C13 | 0.016 (2) | 0.027 (2) | 0.0131 (19) | −0.0091 (16) | −0.0027 (15) | 0.0008 (15) |
C11 | 0.0140 (19) | 0.021 (2) | 0.0130 (19) | −0.0077 (16) | −0.0033 (15) | 0.0007 (14) |
C12 | 0.0110 (18) | 0.024 (2) | 0.0127 (19) | −0.0037 (16) | −0.0023 (15) | 0.0014 (15) |
C10 | 0.0105 (19) | 0.0112 (19) | 0.0146 (19) | −0.0026 (15) | −0.0010 (15) | −0.0037 (14) |
C9 | 0.0141 (19) | 0.0084 (19) | 0.0139 (19) | −0.0041 (15) | −0.0050 (15) | −0.0012 (14) |
N1 | 0.0093 (15) | 0.0134 (16) | 0.0102 (15) | −0.0015 (12) | −0.0043 (12) | 0.0022 (12) |
C1 | 0.0117 (18) | 0.0129 (19) | 0.0138 (19) | −0.0046 (15) | 0.0008 (15) | −0.0041 (14) |
C3' | 0.0109 (18) | 0.0088 (18) | 0.0113 (18) | −0.0023 (14) | −0.0045 (15) | −0.0032 (14) |
C2' | 0.0106 (18) | 0.0076 (18) | 0.0135 (19) | −0.0033 (14) | 0.0001 (14) | −0.0041 (13) |
C4' | 0.018 (2) | 0.0129 (19) | 0.0098 (18) | −0.0050 (15) | −0.0028 (15) | −0.0014 (14) |
C5' | 0.0138 (19) | 0.017 (2) | 0.015 (2) | −0.0052 (15) | −0.0019 (16) | −0.0028 (15) |
C1' | 0.0118 (19) | 0.014 (2) | 0.018 (2) | −0.0009 (15) | −0.0087 (16) | −0.0035 (15) |
O3S | 0.0285 (14) | 0.0231 (14) | 0.0231 (14) | −0.0074 (11) | −0.0113 (11) | −0.0020 (11) |
N2 | 0.0066 (14) | 0.0228 (17) | 0.0080 (15) | −0.0071 (12) | −0.0002 (12) | 0.0017 (12) |
O2S | 0.0267 (14) | 0.0241 (14) | 0.0149 (13) | −0.0113 (11) | −0.0018 (11) | 0.0009 (10) |
C15 | 0.0082 (18) | 0.020 (2) | 0.0122 (18) | 0.0002 (15) | −0.0023 (14) | 0.0023 (14) |
C16 | 0.016 (2) | 0.022 (2) | 0.020 (2) | −0.0043 (16) | −0.0081 (15) | −0.0010 (15) |
Geometric parameters (Å, º) top
O1'—S1 | 1.470 (2) | C8—N2 | 1.390 (3) |
S1—O3' | 1.453 (2) | C8—C9 | 1.407 (4) |
S1—O2' | 1.461 (2) | C14—N2 | 1.470 (3) |
S1—C3' | 1.794 (3) | C14—C13 | 1.505 (4) |
F1—C7 | 1.371 (3) | C11—N2 | 1.481 (4) |
O1—C3 | 1.238 (3) | C11—C12 | 1.506 (4) |
N3—C12 | 1.491 (4) | C10—C9 | 1.394 (4) |
N3—C13 | 1.492 (4) | C10—N1 | 1.408 (4) |
O2—C3 | 1.305 (3) | N1—C1 | 1.337 (3) |
O3—C4 | 1.290 (3) | N1—C15 | 1.478 (3) |
C3—C2 | 1.477 (4) | C3'—C4' | 1.374 (4) |
C2—C1 | 1.369 (4) | C3'—C2' | 1.427 (4) |
C2—C4 | 1.418 (4) | C2'—C1' | 1.416 (4) |
C4—C5 | 1.427 (4) | C2'—C2'i | 1.425 (5) |
C5—C10 | 1.404 (4) | C4'—C5' | 1.408 (4) |
C5—C6 | 1.411 (4) | C5'—C1'i | 1.365 (4) |
C6—C7 | 1.346 (4) | C1'—C5'i | 1.365 (4) |
C7—C8 | 1.416 (4) | C15—C16 | 1.520 (4) |
| | | |
O3'—S1—O2' | 113.96 (12) | N2—C14—C13 | 111.8 (2) |
O3'—S1—O1' | 112.66 (12) | N3—C13—C14 | 111.6 (2) |
O2'—S1—O1' | 111.61 (12) | N2—C11—C12 | 110.6 (2) |
O3'—S1—C3' | 105.74 (13) | N3—C12—C11 | 108.7 (2) |
O2'—S1—C3' | 106.78 (12) | C9—C10—C5 | 120.9 (3) |
O1'—S1—C3' | 105.34 (13) | C9—C10—N1 | 120.8 (3) |
C12—N3—C13 | 110.4 (3) | C5—C10—N1 | 118.3 (3) |
O1—C3—O2 | 122.1 (3) | C10—C9—C8 | 121.4 (3) |
O1—C3—C2 | 122.6 (3) | C1—N1—C10 | 120.2 (2) |
O2—C3—C2 | 115.3 (3) | C1—N1—C15 | 118.7 (2) |
C1—C2—C4 | 119.3 (3) | C10—N1—C15 | 121.1 (2) |
C1—C2—C3 | 120.1 (3) | N1—C1—C2 | 123.5 (3) |
C4—C2—C3 | 120.6 (3) | C4'—C3'—C2' | 120.6 (3) |
O3—C4—C2 | 121.1 (3) | C4'—C3'—S1 | 117.5 (2) |
O3—C4—C5 | 121.3 (3) | C2'—C3'—S1 | 121.8 (2) |
C2—C4—C5 | 117.5 (3) | C1'—C2'—C2'i | 118.9 (3) |
C10—C5—C6 | 117.9 (3) | C1'—C2'—C3' | 122.6 (3) |
C10—C5—C4 | 120.9 (3) | C2'i—C2'—C3' | 118.5 (3) |
C6—C5—C4 | 121.2 (3) | C3'—C4'—C5' | 120.5 (3) |
C7—C6—C5 | 119.9 (3) | C1'i—C5'—C4' | 120.2 (3) |
C6—C7—F1 | 116.8 (3) | C5'i—C1'—C2' | 121.3 (3) |
C6—C7—C8 | 124.2 (3) | C8—N2—C14 | 117.4 (2) |
F1—C7—C8 | 119.0 (3) | C8—N2—C11 | 119.2 (2) |
N2—C8—C9 | 122.0 (3) | C14—N2—C11 | 111.1 (2) |
N2—C8—C7 | 122.5 (3) | N1—C15—C16 | 112.8 (2) |
C9—C8—C7 | 115.3 (3) | | |
| | | |
O1—C3—C2—C1 | −7.9 (5) | C5—C10—N1—C1 | 1.9 (4) |
O2—C3—C2—C1 | 172.6 (3) | C9—C10—N1—C15 | 0.8 (4) |
O1—C3—C2—C4 | 171.8 (3) | C5—C10—N1—C15 | −178.8 (3) |
O2—C3—C2—C4 | −7.7 (4) | C10—N1—C1—C2 | −2.5 (4) |
C1—C2—C4—O3 | −178.1 (3) | C15—N1—C1—C2 | 178.1 (3) |
C3—C2—C4—O3 | 2.2 (4) | C4—C2—C1—N1 | 0.0 (4) |
C1—C2—C4—C5 | 3.0 (4) | C3—C2—C1—N1 | 179.7 (3) |
C3—C2—C4—C5 | −176.8 (3) | O3'—S1—C3'—C4' | 1.7 (3) |
O3—C4—C5—C10 | 177.5 (3) | O2'—S1—C3'—C4' | −120.0 (2) |
C2—C4—C5—C10 | −3.5 (4) | O1'—S1—C3'—C4' | 121.2 (2) |
O3—C4—C5—C6 | −4.7 (4) | O3'—S1—C3'—C2' | −176.6 (2) |
C2—C4—C5—C6 | 174.3 (3) | O2'—S1—C3'—C2' | 61.7 (3) |
C10—C5—C6—C7 | 1.9 (4) | O1'—S1—C3'—C2' | −57.0 (3) |
C4—C5—C6—C7 | −176.0 (3) | C4'—C3'—C2'—C1' | 178.6 (3) |
C5—C6—C7—F1 | 172.1 (2) | S1—C3'—C2'—C1' | −3.2 (4) |
C5—C6—C7—C8 | −6.4 (5) | C4'—C3'—C2'—C2'i | −2.4 (5) |
C6—C7—C8—N2 | −179.5 (3) | S1—C3'—C2'—C2'i | 175.8 (3) |
F1—C7—C8—N2 | 2.0 (4) | C2'—C3'—C4'—C5' | 1.8 (4) |
C6—C7—C8—C9 | 5.0 (4) | S1—C3'—C4'—C5' | −176.5 (2) |
F1—C7—C8—C9 | −173.5 (2) | C3'—C4'—C5'—C1'i | 0.2 (4) |
C12—N3—C13—C14 | −55.6 (3) | C2'i—C2'—C1'—C5'i | −1.1 (5) |
N2—C14—C13—N3 | 52.8 (3) | C3'—C2'—C1'—C5'i | 177.9 (3) |
C13—N3—C12—C11 | 59.0 (3) | C9—C8—N2—C14 | −3.9 (4) |
N2—C11—C12—N3 | −60.6 (3) | C7—C8—N2—C14 | −179.2 (3) |
C6—C5—C10—C9 | 3.7 (4) | C9—C8—N2—C11 | −142.8 (3) |
C4—C5—C10—C9 | −178.4 (3) | C7—C8—N2—C11 | 42.0 (4) |
C6—C5—C10—N1 | −176.7 (3) | C13—C14—N2—C8 | 164.2 (3) |
C4—C5—C10—N1 | 1.1 (4) | C13—C14—N2—C11 | −53.9 (3) |
C5—C10—C9—C8 | −5.1 (4) | C12—C11—N2—C8 | −160.5 (3) |
N1—C10—C9—C8 | 175.4 (3) | C12—C11—N2—C14 | 58.3 (3) |
N2—C8—C9—C10 | −174.7 (3) | C1—N1—C15—C16 | 99.2 (3) |
C7—C8—C9—C10 | 0.9 (4) | C10—N1—C15—C16 | −80.1 (3) |
C9—C10—N1—C1 | −178.5 (3) | | |
Symmetry code: (i) −x+2, −y, −z+2. |
Crystal data top
C26H23FN3O10S | F(000) = 2440 |
Mr = 588.54 | Dx = 1.462 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
a = 11.6515 (3) Å | µ = 0.19 mm−1 |
b = 7.4209 (2) Å | T = 100 K |
c = 61.8325 (18) Å | Sheet, colourless |
V = 5346.3 (3) Å3 | 0.30 × 0.04 × 0.03 mm |
Z = 8 | |
Data collection top
CCD area detector diffractometer | 5987 independent reflections |
Radiation source: fine-focus sealed tube | 3739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.103 |
phi and ω scans | θmax = 27.5°, θmin = 0.7° |
Absorption correction: empirical (using intensity measurements) SADABS | h = −12→14 |
Tmin = 0.948, Tmax = 0.995 | k = −9→9 |
47387 measured reflections | l = −80→73 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.068 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H 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 parameters | Δρmax = 0.43 e Å−3 |
4 restraints | Δρmin = −0.40 e Å−3 |
Crystal data top
C26H23FN3O10S | V = 5346.3 (3) Å3 |
Mr = 588.54 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.6515 (3) Å | µ = 0.19 mm−1 |
b = 7.4209 (2) Å | T = 100 K |
c = 61.8325 (18) Å | 0.30 × 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 = 0.995 | Rint = 0.103 |
47387 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.068 | 4 restraints |
wR(F2) = 0.164 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | Δρmax = 0.43 e Å−3 |
5987 reflections | Δρmin = −0.40 e Å−3 |
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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
S1' | 0.48089 (7) | 0.27147 (11) | 0.179103 (13) | 0.0196 (2) | |
F1 | 0.35001 (17) | 0.3205 (3) | 0.11186 (3) | 0.0286 (5) | |
O3' | 0.5662 (2) | 0.4165 (3) | 0.18138 (4) | 0.0252 (6) | |
O2' | 0.5345 (2) | 0.1008 (3) | 0.17323 (4) | 0.0256 (6) | |
C7 | 0.1635 (3) | 0.3845 (4) | 0.09842 (5) | 0.0204 (8) | |
O1' | 0.3868 (2) | 0.3218 (3) | 0.16499 (4) | 0.0280 (6) | |
C1' | 0.4770 (3) | 0.2951 (4) | 0.22329 (5) | 0.0164 (7) | |
H1' | 0.5476 | 0.3527 | 0.2221 | 0.020* | |
C4' | 0.2631 (3) | 0.1236 (4) | 0.22610 (5) | 0.0196 (7) | |
H4' | 0.1919 | 0.0673 | 0.2268 | 0.023* | |
C5' | 0.3179 (3) | 0.1803 (4) | 0.24543 (5) | 0.0169 (7) | |
C3' | 0.3139 (3) | 0.1506 (4) | 0.20635 (5) | 0.0196 (8) | |
H3' | 0.2778 | 0.1110 | 0.1938 | 0.024* | |
C10' | 0.4272 (3) | 0.2656 (4) | 0.24409 (5) | 0.0146 (7) | |
C6' | 0.2675 (3) | 0.1530 (4) | 0.26612 (5) | 0.0200 (7) | |
H6' | 0.1962 | 0.0975 | 0.2672 | 0.024* | |
C8' | 0.4314 (3) | 0.2900 (4) | 0.28304 (5) | 0.0219 (8) | |
H8' | 0.4687 | 0.3258 | 0.2956 | 0.026* | |
C2' | 0.4214 (3) | 0.2390 (4) | 0.20519 (5) | 0.0169 (7) | |
N2 | 0.1157 (3) | 0.3076 (4) | 0.11711 (4) | 0.0213 (6) | |
N3 | −0.0025 (3) | 0.2150 (4) | 0.15587 (5) | 0.0301 (8) | |
C9' | 0.4824 (3) | 0.3179 (4) | 0.26351 (5) | 0.0183 (7) | |
H9' | 0.5543 | 0.3720 | 0.2629 | 0.022* | |
C7' | 0.3230 (3) | 0.2076 (4) | 0.28433 (5) | 0.0225 (8) | |
H7' | 0.2889 | 0.1902 | 0.2978 | 0.027* | |
C9 | 0.3348 (3) | 0.4535 (5) | 0.07762 (5) | 0.0241 (8) | |
H9 | 0.4145 | 0.4553 | 0.0767 | 0.029* | |
C5 | 0.1493 (3) | 0.5138 (5) | 0.06240 (5) | 0.0239 (8) | |
O1 | 0.4300 (3) | 0.5791 (4) | 0.03843 (4) | 0.0468 (8) | |
N1 | 0.0811 (3) | 0.5803 (4) | 0.04557 (5) | 0.0334 (8) | |
C8 | 0.2835 (3) | 0.3896 (5) | 0.09580 (5) | 0.0222 (8) | |
C14 | −0.0070 (3) | 0.2688 (5) | 0.11660 (6) | 0.0285 (9) | |
H14A | −0.0275 | 0.2171 | 0.1027 | 0.034* | |
H14B | −0.0502 | 0.3794 | 0.1185 | 0.034* | |
C1 | 0.3225 (4) | 0.5815 (5) | 0.04072 (6) | 0.0300 (9) | |
O2 | 0.4042 (3) | 0.7186 (4) | 0.00143 (4) | 0.0530 (9) | |
H2 | 0.4335 | 0.6732 | 0.0122 | 0.080* | |
C6 | 0.0972 (3) | 0.4487 (4) | 0.08137 (5) | 0.0244 (8) | |
H6 | 0.0176 | 0.4486 | 0.0825 | 0.029* | |
C12 | 0.1201 (3) | 0.2678 (5) | 0.15635 (5) | 0.0254 (8) | |
H12A | 0.1677 | 0.1607 | 0.1555 | 0.031* | |
H12B | 0.1369 | 0.3279 | 0.1699 | 0.031* | |
O3 | 0.2300 (3) | 0.7879 (5) | −0.00994 (4) | 0.0551 (9) | |
C10 | 0.2685 (3) | 0.5164 (5) | 0.06037 (5) | 0.0241 (8) | |
C13 | −0.0360 (3) | 0.1380 (5) | 0.13452 (5) | 0.0292 (9) | |
H13A | −0.1178 | 0.1133 | 0.1344 | 0.035* | |
H13B | 0.0043 | 0.0253 | 0.1322 | 0.035* | |
C2 | 0.2474 (4) | 0.6479 (5) | 0.02445 (5) | 0.0294 (9) | |
C11 | 0.1482 (4) | 0.3922 (4) | 0.13774 (5) | 0.0276 (9) | |
H11A | 0.1070 | 0.5049 | 0.1395 | 0.033* | |
H11B | 0.2297 | 0.4184 | 0.1377 | 0.033* | |
C4 | 0.1317 (4) | 0.6449 (5) | 0.02762 (6) | 0.0325 (10) | |
H4 | 0.0849 | 0.6903 | 0.0167 | 0.039* | |
C3 | 0.2915 (4) | 0.7227 (6) | 0.00377 (6) | 0.0396 (11) | |
C15 | −0.0474 (4) | 0.5874 (8) | 0.04713 (7) | 0.0520 (14) | |
O2S | 0.8206 (11) | 0.768 (3) | 0.11484 (18) | 0.120 (6) | 0.61 (4) |
O4S | 0.6648 (6) | 0.5048 (11) | 0.04821 (10) | 0.051 (3) | 0.467 (10) |
O4S' | 0.6546 (6) | 0.6739 (12) | 0.05658 (12) | 0.081 (3) | 0.533 (10) |
O3S | 0.722 (2) | 0.055 (2) | 0.0921 (2) | 0.073 (8) | 0.42 (5) |
C16 | −0.0964 (8) | 0.4282 (13) | 0.04290 (15) | 0.048 (2) | 0.50 |
C16' | −0.0946 (8) | 0.7322 (18) | 0.05749 (16) | 0.066 (3) | 0.50 |
O3S' | 0.788 (4) | 0.016 (5) | 0.0925 (2) | 0.182 (11) | 0.58 (5) |
O1S | 0.7765 (2) | 0.4094 (4) | 0.15897 (4) | 0.0376 (7) | |
H1B | 0.7144 | 0.4237 | 0.1649 | 0.056* | |
H1A | 0.8095 | 0.5100 | 0.1634 | 0.056* | |
H101 | −0.018 (4) | 0.133 (5) | 0.1655 (6) | 0.074 (17)* | |
H100 | −0.042 (3) | 0.313 (4) | 0.1587 (6) | 0.040 (12)* | |
O2S' | 0.790 (4) | 0.858 (9) | 0.1162 (6) | 0.31 (3) | 0.39 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1' | 0.0206 (5) | 0.0208 (4) | 0.0175 (4) | −0.0030 (3) | −0.0005 (4) | 0.0032 (3) |
F1 | 0.0293 (13) | 0.0356 (12) | 0.0209 (11) | −0.0010 (9) | −0.0053 (9) | 0.0062 (8) |
O3' | 0.0259 (14) | 0.0293 (13) | 0.0203 (12) | −0.0099 (11) | 0.0008 (11) | 0.0043 (10) |
O2' | 0.0279 (15) | 0.0272 (13) | 0.0217 (13) | 0.0011 (11) | 0.0044 (11) | 0.0003 (10) |
C7 | 0.028 (2) | 0.0191 (16) | 0.0138 (16) | −0.0040 (15) | 0.0009 (15) | −0.0010 (13) |
O1' | 0.0255 (15) | 0.0358 (14) | 0.0226 (13) | −0.0020 (11) | −0.0068 (11) | 0.0094 (11) |
C1' | 0.0100 (17) | 0.0171 (15) | 0.0219 (17) | −0.0002 (13) | −0.0007 (14) | 0.0035 (12) |
C4' | 0.0129 (19) | 0.0164 (16) | 0.0294 (19) | −0.0008 (13) | 0.0005 (15) | 0.0046 (13) |
C5' | 0.0149 (18) | 0.0111 (15) | 0.0248 (18) | 0.0024 (13) | −0.0011 (15) | 0.0006 (12) |
C3' | 0.023 (2) | 0.0169 (16) | 0.0189 (18) | −0.0007 (14) | −0.0046 (15) | 0.0020 (12) |
C10' | 0.0146 (18) | 0.0094 (14) | 0.0198 (16) | 0.0026 (13) | 0.0000 (13) | −0.0005 (12) |
C6' | 0.017 (2) | 0.0152 (16) | 0.0279 (19) | 0.0014 (13) | 0.0049 (16) | 0.0026 (13) |
C8' | 0.027 (2) | 0.0206 (17) | 0.0182 (18) | −0.0002 (15) | −0.0028 (15) | −0.0008 (13) |
C2' | 0.0132 (18) | 0.0166 (15) | 0.0208 (17) | 0.0011 (13) | −0.0007 (14) | 0.0048 (13) |
N2 | 0.0257 (18) | 0.0252 (15) | 0.0131 (14) | −0.0035 (13) | 0.0007 (12) | 0.0017 (11) |
N3 | 0.040 (2) | 0.0278 (17) | 0.0229 (17) | 0.0133 (15) | 0.0103 (15) | 0.0089 (13) |
C9' | 0.0145 (18) | 0.0132 (15) | 0.0271 (18) | 0.0000 (13) | −0.0014 (15) | 0.0020 (12) |
C7' | 0.026 (2) | 0.0198 (17) | 0.0218 (18) | 0.0041 (15) | 0.0050 (15) | 0.0031 (13) |
C9 | 0.024 (2) | 0.0290 (19) | 0.0188 (18) | −0.0047 (16) | 0.0044 (16) | −0.0010 (14) |
C5 | 0.033 (2) | 0.0246 (18) | 0.0140 (17) | −0.0026 (15) | −0.0047 (16) | 0.0014 (13) |
O1 | 0.0344 (19) | 0.073 (2) | 0.0326 (16) | −0.0078 (16) | 0.0090 (14) | 0.0164 (15) |
N1 | 0.037 (2) | 0.044 (2) | 0.0193 (16) | −0.0025 (16) | −0.0009 (15) | 0.0095 (14) |
C8 | 0.028 (2) | 0.0240 (18) | 0.0146 (17) | −0.0017 (15) | −0.0050 (15) | −0.0003 (13) |
C14 | 0.028 (2) | 0.037 (2) | 0.0206 (18) | 0.0008 (17) | 0.0061 (16) | 0.0078 (15) |
C1 | 0.038 (3) | 0.032 (2) | 0.0200 (19) | −0.0062 (18) | 0.0027 (18) | 0.0004 (15) |
O2 | 0.055 (2) | 0.074 (2) | 0.0296 (16) | −0.0059 (18) | 0.0098 (15) | 0.0195 (15) |
C6 | 0.027 (2) | 0.0266 (18) | 0.0197 (18) | −0.0045 (15) | −0.0015 (16) | 0.0019 (14) |
C12 | 0.041 (2) | 0.0208 (17) | 0.0144 (17) | 0.0015 (16) | 0.0022 (15) | 0.0007 (13) |
O3 | 0.069 (2) | 0.071 (2) | 0.0254 (16) | 0.0153 (18) | 0.0114 (16) | 0.0220 (15) |
C10 | 0.034 (2) | 0.0237 (18) | 0.0146 (17) | −0.0056 (16) | 0.0032 (16) | 0.0005 (13) |
C13 | 0.026 (2) | 0.039 (2) | 0.0225 (19) | −0.0008 (17) | 0.0067 (17) | 0.0071 (16) |
C2 | 0.044 (3) | 0.0283 (19) | 0.0157 (18) | −0.0016 (18) | 0.0019 (18) | 0.0030 (14) |
C11 | 0.049 (3) | 0.0199 (17) | 0.0136 (17) | 0.0003 (16) | 0.0023 (17) | 0.0012 (13) |
C4 | 0.051 (3) | 0.032 (2) | 0.0155 (18) | 0.0009 (19) | −0.0041 (18) | 0.0044 (15) |
C3 | 0.057 (3) | 0.039 (2) | 0.023 (2) | −0.001 (2) | 0.008 (2) | 0.0054 (17) |
C15 | 0.028 (3) | 0.093 (4) | 0.035 (3) | −0.003 (3) | −0.008 (2) | 0.023 (3) |
O2S | 0.093 (7) | 0.214 (14) | 0.054 (6) | −0.006 (9) | 0.023 (5) | 0.038 (8) |
O4S | 0.043 (5) | 0.067 (6) | 0.042 (4) | −0.007 (4) | −0.013 (3) | 0.014 (4) |
O4S' | 0.075 (5) | 0.097 (8) | 0.070 (5) | 0.026 (5) | 0.015 (4) | 0.034 (5) |
O3S | 0.041 (11) | 0.138 (15) | 0.039 (6) | 0.001 (7) | 0.004 (6) | −0.007 (6) |
C16 | 0.033 (6) | 0.061 (6) | 0.050 (6) | 0.002 (5) | −0.005 (4) | −0.004 (5) |
C16' | 0.024 (6) | 0.133 (11) | 0.039 (6) | 0.009 (6) | −0.002 (4) | −0.003 (6) |
O3S' | 0.13 (3) | 0.37 (2) | 0.052 (7) | −0.08 (2) | 0.002 (9) | −0.053 (10) |
O1S | 0.0274 (17) | 0.0457 (17) | 0.0396 (16) | 0.0089 (13) | −0.0001 (13) | −0.0081 (13) |
O2S' | 0.17 (3) | 0.45 (6) | 0.31 (4) | −0.19 (3) | 0.10 (3) | −0.27 (5) |
Geometric parameters (Å, º) top
S1'—O1' | 1.450 (2) | N3—C12 | 1.481 (5) |
S1'—O2' | 1.458 (2) | N3—C13 | 1.491 (5) |
S1'—O3' | 1.471 (2) | C9—C8 | 1.358 (5) |
S1'—C2' | 1.772 (3) | C9—C10 | 1.398 (5) |
F1—C8 | 1.360 (4) | C5—C10 | 1.395 (5) |
C7—C6 | 1.391 (5) | C5—N1 | 1.399 (4) |
C7—N2 | 1.404 (4) | C5—C6 | 1.406 (5) |
C7—C8 | 1.409 (5) | O1—C1 | 1.260 (5) |
C1'—C2' | 1.358 (4) | N1—C4 | 1.345 (4) |
C1'—C10' | 1.428 (4) | N1—C15 | 1.501 (5) |
C4'—C3' | 1.371 (4) | C14—C13 | 1.512 (5) |
C4'—C5' | 1.419 (4) | C1—C2 | 1.422 (5) |
C5'—C6' | 1.422 (5) | C1—C10 | 1.452 (5) |
C5'—C10' | 1.424 (4) | O2—C3 | 1.321 (5) |
C3'—C2' | 1.416 (4) | C12—C11 | 1.511 (4) |
C10'—C9' | 1.416 (4) | O3—C3 | 1.211 (5) |
C6'—C7' | 1.360 (5) | C2—C4 | 1.362 (6) |
C8'—C9' | 1.362 (5) | C2—C3 | 1.486 (5) |
C8'—C7' | 1.406 (5) | C15—C16 | 1.338 (10) |
N2—C14 | 1.459 (5) | C15—C16' | 1.367 (12) |
N2—C11 | 1.471 (4) | | |
| | | |
O1'—S1'—O2' | 113.45 (15) | C10—C5—N1 | 119.6 (3) |
O1'—S1'—O3' | 112.31 (14) | C10—C5—C6 | 120.6 (3) |
O2'—S1'—O3' | 111.68 (14) | N1—C5—C6 | 119.8 (3) |
O1'—S1'—C2' | 106.68 (15) | C4—N1—C5 | 119.4 (3) |
O2'—S1'—C2' | 106.03 (14) | C4—N1—C15 | 118.5 (3) |
O3'—S1'—C2' | 106.05 (14) | C5—N1—C15 | 122.1 (3) |
C6—C7—N2 | 122.9 (3) | C9—C8—F1 | 119.0 (3) |
C6—C7—C8 | 117.1 (3) | C9—C8—C7 | 122.8 (3) |
N2—C7—C8 | 119.9 (3) | F1—C8—C7 | 118.1 (3) |
C2'—C1'—C10' | 120.1 (3) | N2—C14—C13 | 109.3 (3) |
C3'—C4'—C5' | 120.9 (3) | O1—C1—C2 | 122.5 (3) |
C4'—C5'—C6' | 122.0 (3) | O1—C1—C10 | 121.4 (3) |
C4'—C5'—C10' | 119.0 (3) | C2—C1—C10 | 116.1 (4) |
C6'—C5'—C10' | 119.0 (3) | C7—C6—C5 | 120.7 (3) |
C4'—C3'—C2' | 119.6 (3) | N3—C12—C11 | 110.8 (3) |
C9'—C10'—C5' | 118.6 (3) | C5—C10—C9 | 118.5 (3) |
C9'—C10'—C1' | 122.5 (3) | C5—C10—C1 | 120.8 (3) |
C5'—C10'—C1' | 118.9 (3) | C9—C10—C1 | 120.7 (3) |
C7'—C6'—C5' | 120.4 (3) | N3—C13—C14 | 110.1 (3) |
C9'—C8'—C7' | 120.5 (3) | C4—C2—C1 | 120.1 (3) |
C1'—C2'—C3' | 121.5 (3) | C4—C2—C3 | 118.2 (4) |
C1'—C2'—S1' | 121.5 (3) | C1—C2—C3 | 121.7 (4) |
C3'—C2'—S1' | 117.1 (2) | N2—C11—C12 | 110.1 (3) |
C7—N2—C14 | 116.8 (3) | N1—C4—C2 | 123.9 (4) |
C7—N2—C11 | 116.0 (3) | O3—C3—O2 | 121.4 (4) |
C14—N2—C11 | 110.8 (3) | O3—C3—C2 | 123.2 (4) |
C12—N3—C13 | 111.8 (3) | O2—C3—C2 | 115.5 (4) |
C8'—C9'—C10' | 120.8 (3) | C16—C15—C16' | 127.9 (7) |
C6'—C7'—C8' | 120.6 (3) | C16—C15—N1 | 112.4 (6) |
C8—C9—C10 | 120.3 (3) | C16'—C15—N1 | 117.3 (6) |
Crystal data top
C23H26FN3O7 | V = 1136.71 (10) Å3 |
Mr = 475.47 | Z = 2 |
Triclinic, P1 | F(000) = 500.0 |
a = 7.0237 (4) Å | Dx = 1.389 Mg m−3 |
b = 9.9645 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 17.4655 (9) Å | µ = 0.11 mm−1 |
α = 91.100 (3)° | T = 296 K |
β = 97.543 (3)° | Sheet, colorless |
γ = 109.906 (3)° | 0.15 × 0.06 × 0.03 mm |
Data collection top
CCD area detector diffractometer | 5221 independent reflections |
Radiation source: fine-focus sealed tube | 2989 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
phi and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: empirical (using intensity measurements) SADABS | h = −9→9 |
Tmin = 0.984, Tmax = 0.997 | k = −12→12 |
17531 measured reflections | l = −22→22 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.112 | H 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 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Crystal data top
C23H26FN3O7 | γ = 109.906 (3)° |
Mr = 475.47 | V = 1136.71 (10) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.0237 (4) Å | Mo Kα radiation |
b = 9.9645 (5) Å | µ = 0.11 mm−1 |
c = 17.4655 (9) Å | T = 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 = 0.997 | Rint = 0.029 |
17531 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.112 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | Δρmax = 0.17 e Å−3 |
5221 reflections | Δρmin = −0.20 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
F1 | 0.82208 (17) | −0.33285 (9) | 0.61457 (6) | 0.0581 (3) | |
O2 | 0.54571 (18) | 0.03225 (15) | 0.27079 (7) | 0.0529 (3) | |
H2 | 0.553 (3) | −0.051 (2) | 0.2947 (12) | 0.079* | |
O1S | 0.2611 (3) | 0.0897 (2) | 0.04954 (10) | 0.0715 (4) | |
O1 | 0.6433 (2) | 0.26226 (14) | 0.30653 (7) | 0.0662 (4) | |
O3 | 0.61812 (17) | −0.13846 (12) | 0.36964 (6) | 0.0482 (3) | |
O3' | 0.7482 (3) | 0.28716 (17) | 0.78613 (8) | 0.0790 (5) | |
H1' | 0.812 (4) | 0.249 (3) | 0.8283 (16) | 0.118* | |
O2' | 0.8187 (2) | 0.19293 (15) | 0.91645 (8) | 0.0699 (4) | |
O1' | 0.65917 (19) | 0.21929 (14) | 1.01326 (7) | 0.0595 (4) | |
N1 | 0.78967 (19) | 0.19248 (12) | 0.53606 (7) | 0.0349 (3) | |
N2 | 0.93994 (19) | −0.11350 (13) | 0.73272 (7) | 0.0383 (3) | |
N3 | 1.0486 (2) | −0.15138 (14) | 0.89301 (7) | 0.0438 (4) | |
H15 | 1.1361 | −0.1707 | 0.9298 | 0.053* | |
H14 | 0.9486 | −0.1374 | 0.9159 | 0.053* | |
C3 | 0.6252 (2) | 0.1420 (2) | 0.32344 (10) | 0.0450 (4) | |
C2 | 0.6840 (2) | 0.10546 (17) | 0.40286 (9) | 0.0360 (4) | |
C1 | 0.7373 (2) | 0.20978 (16) | 0.46120 (9) | 0.0373 (4) | |
H1 | 0.7374 | 0.2999 | 0.4482 | 0.045* | |
C10 | 0.7977 (2) | 0.05996 (15) | 0.55761 (8) | 0.0312 (3) | |
C9 | 0.8576 (2) | 0.03828 (16) | 0.63500 (9) | 0.0339 (4) | |
H8 | 0.8927 | 0.1139 | 0.6723 | 0.041* | |
C8 | 0.8660 (2) | −0.09337 (16) | 0.65762 (9) | 0.0343 (4) | |
C11 | 1.0267 (3) | 0.01119 (17) | 0.78827 (9) | 0.0446 (4) | |
H11 | 0.9169 | 0.0355 | 0.8063 | 0.054* | |
H10 | 1.1085 | 0.0923 | 0.7631 | 0.054* | |
C12 | 1.1588 (3) | −0.01935 (18) | 0.85661 (9) | 0.0467 (4) | |
H13 | 1.2795 | −0.0292 | 0.8394 | 0.056* | |
H12 | 1.2037 | 0.0611 | 0.8949 | 0.056* | |
C4 | 0.6764 (2) | −0.03538 (17) | 0.42026 (9) | 0.0353 (4) | |
C5 | 0.7397 (2) | −0.05309 (16) | 0.50056 (9) | 0.0328 (4) | |
C6 | 0.7441 (2) | −0.18632 (16) | 0.52364 (9) | 0.0368 (4) | |
H9 | 0.7029 | −0.2638 | 0.4872 | 0.044* | |
C7 | 0.8070 (2) | −0.20340 (16) | 0.59774 (9) | 0.0377 (4) | |
C14 | 0.8209 (3) | −0.23983 (18) | 0.77048 (10) | 0.0500 (5) | |
H18 | 0.7614 | −0.3211 | 0.7328 | 0.060* | |
H19 | 0.7104 | −0.2208 | 0.7912 | 0.060* | |
C13 | 0.9586 (3) | −0.27426 (18) | 0.83510 (10) | 0.0525 (5) | |
H16 | 0.8803 | −0.3577 | 0.8596 | 0.063* | |
H17 | 1.0669 | −0.2959 | 0.8142 | 0.063* | |
C15 | 0.8401 (3) | 0.31597 (16) | 0.59305 (10) | 0.0441 (4) | |
H4 | 0.7944 | 0.2819 | 0.6414 | 0.053* | |
H3 | 0.7675 | 0.3787 | 0.5740 | 0.053* | |
C16 | 1.0657 (3) | 0.3989 (2) | 0.60746 (12) | 0.0631 (6) | |
H7 | 1.1373 | 0.3387 | 0.6291 | 0.095* | |
H6 | 1.0920 | 0.4800 | 0.6430 | 0.095* | |
H5 | 1.1119 | 0.4312 | 0.5595 | 0.095* | |
C5' | 0.3426 (4) | 0.4400 (2) | 0.87721 (14) | 0.0801 (7) | |
H4' | 0.2519 | 0.4762 | 0.8970 | 0.096* | |
C6' | 0.4481 (3) | 0.3696 (2) | 0.92331 (12) | 0.0623 (5) | |
H5' | 0.4267 | 0.3576 | 0.9745 | 0.075* | |
C1' | 0.5853 (3) | 0.31638 (17) | 0.89481 (10) | 0.0444 (4) | |
C2' | 0.6148 (3) | 0.33448 (17) | 0.81754 (11) | 0.0512 (5) | |
C7' | 0.6953 (3) | 0.23853 (18) | 0.94519 (11) | 0.0477 (4) | |
C4' | 0.3748 (4) | 0.4556 (2) | 0.80116 (14) | 0.0788 (7) | |
H3' | 0.3054 | 0.5035 | 0.7697 | 0.095* | |
C3' | 0.5051 (4) | 0.4027 (2) | 0.77122 (12) | 0.0679 (6) | |
H2' | 0.5212 | 0.4121 | 0.7194 | 0.081* | |
H1A | 0.376 (4) | 0.137 (3) | 0.0435 (16) | 0.108 (11)* | |
H1B | 0.243 (4) | −0.001 (3) | 0.0584 (15) | 0.114 (10)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1 | 0.0853 (8) | 0.0407 (5) | 0.0530 (7) | 0.0318 (5) | −0.0017 (5) | 0.0053 (5) |
O2 | 0.0554 (8) | 0.0678 (9) | 0.0296 (7) | 0.0154 (6) | 0.0015 (5) | 0.0057 (6) |
O1S | 0.0715 (12) | 0.0779 (11) | 0.0821 (12) | 0.0398 (10) | 0.0305 (9) | 0.0228 (9) |
O1 | 0.0796 (9) | 0.0619 (9) | 0.0480 (8) | 0.0185 (7) | −0.0085 (7) | 0.0210 (7) |
O3 | 0.0570 (7) | 0.0511 (7) | 0.0333 (7) | 0.0174 (6) | −0.0005 (5) | −0.0047 (6) |
O3' | 0.1017 (12) | 0.0968 (12) | 0.0488 (10) | 0.0430 (10) | 0.0225 (8) | 0.0154 (8) |
O2' | 0.0807 (10) | 0.0890 (10) | 0.0635 (10) | 0.0541 (9) | 0.0227 (8) | 0.0231 (8) |
O1' | 0.0638 (9) | 0.0843 (9) | 0.0421 (8) | 0.0404 (7) | 0.0056 (6) | 0.0200 (7) |
N1 | 0.0394 (7) | 0.0341 (7) | 0.0302 (8) | 0.0123 (6) | 0.0021 (6) | 0.0043 (6) |
N2 | 0.0430 (8) | 0.0374 (7) | 0.0303 (8) | 0.0114 (6) | −0.0036 (6) | 0.0067 (6) |
N3 | 0.0463 (8) | 0.0594 (9) | 0.0304 (8) | 0.0256 (7) | 0.0011 (6) | 0.0093 (7) |
C3 | 0.0366 (9) | 0.0580 (11) | 0.0355 (10) | 0.0103 (8) | 0.0035 (7) | 0.0095 (9) |
C2 | 0.0309 (8) | 0.0451 (9) | 0.0288 (9) | 0.0094 (7) | 0.0026 (6) | 0.0066 (7) |
C1 | 0.0360 (9) | 0.0391 (9) | 0.0352 (10) | 0.0110 (7) | 0.0036 (7) | 0.0101 (7) |
C10 | 0.0294 (8) | 0.0334 (8) | 0.0299 (9) | 0.0095 (6) | 0.0043 (6) | 0.0050 (7) |
C9 | 0.0343 (8) | 0.0364 (8) | 0.0294 (9) | 0.0110 (7) | 0.0029 (6) | 0.0019 (7) |
C8 | 0.0313 (8) | 0.0392 (9) | 0.0317 (9) | 0.0120 (7) | 0.0019 (6) | 0.0063 (7) |
C11 | 0.0556 (11) | 0.0424 (9) | 0.0324 (10) | 0.0145 (8) | 0.0008 (8) | 0.0043 (7) |
C12 | 0.0492 (10) | 0.0546 (10) | 0.0301 (10) | 0.0120 (8) | 0.0003 (8) | 0.0037 (8) |
C4 | 0.0298 (8) | 0.0431 (9) | 0.0305 (9) | 0.0095 (7) | 0.0044 (7) | −0.0005 (8) |
C5 | 0.0291 (8) | 0.0390 (8) | 0.0303 (9) | 0.0118 (7) | 0.0040 (6) | 0.0036 (7) |
C6 | 0.0383 (9) | 0.0363 (8) | 0.0339 (10) | 0.0120 (7) | 0.0022 (7) | −0.0030 (7) |
C7 | 0.0402 (9) | 0.0324 (8) | 0.0415 (10) | 0.0150 (7) | 0.0023 (7) | 0.0052 (7) |
C14 | 0.0539 (11) | 0.0479 (10) | 0.0385 (10) | 0.0084 (8) | −0.0037 (8) | 0.0134 (8) |
C13 | 0.0707 (12) | 0.0468 (10) | 0.0380 (11) | 0.0214 (9) | −0.0029 (9) | 0.0094 (8) |
C15 | 0.0612 (11) | 0.0350 (9) | 0.0381 (10) | 0.0214 (8) | 0.0009 (8) | 0.0007 (7) |
C16 | 0.0714 (13) | 0.0448 (10) | 0.0596 (13) | 0.0095 (9) | −0.0065 (10) | −0.0081 (9) |
C5' | 0.1024 (18) | 0.0834 (16) | 0.0710 (17) | 0.0610 (14) | −0.0079 (13) | 0.0074 (13) |
C6' | 0.0801 (14) | 0.0640 (12) | 0.0493 (12) | 0.0373 (11) | −0.0020 (10) | 0.0087 (10) |
C1' | 0.0527 (11) | 0.0370 (9) | 0.0393 (11) | 0.0139 (8) | −0.0038 (8) | 0.0034 (7) |
C2' | 0.0656 (12) | 0.0385 (9) | 0.0406 (11) | 0.0104 (9) | −0.0026 (9) | 0.0033 (8) |
C7' | 0.0512 (11) | 0.0490 (10) | 0.0423 (12) | 0.0184 (9) | 0.0012 (9) | 0.0089 (8) |
C4' | 0.1052 (19) | 0.0601 (13) | 0.0657 (17) | 0.0367 (13) | −0.0294 (14) | 0.0091 (11) |
C3' | 0.0963 (17) | 0.0536 (12) | 0.0419 (12) | 0.0172 (12) | −0.0087 (11) | 0.0109 (10) |
Geometric parameters (Å, º) top
F1—C7 | 1.3640 (17) | C11—H11 | 0.9700 |
O2—C3 | 1.328 (2) | C11—H10 | 0.9700 |
O2—H2 | 0.95 (2) | C12—H13 | 0.9700 |
O1S—H1A | 0.80 (3) | C12—H12 | 0.9700 |
O1S—H1B | 0.89 (3) | C4—C5 | 1.447 (2) |
O1—C3 | 1.208 (2) | C5—C6 | 1.404 (2) |
O3—C4 | 1.2601 (17) | C6—C7 | 1.345 (2) |
O3'—C2' | 1.352 (2) | C6—H9 | 0.9300 |
O3'—H1' | 0.97 (3) | C14—C13 | 1.510 (2) |
O2'—C7' | 1.258 (2) | C14—H18 | 0.9700 |
O1'—C7' | 1.253 (2) | C14—H19 | 0.9700 |
N1—C1 | 1.3418 (18) | C13—H16 | 0.9700 |
N1—C10 | 1.3974 (18) | C13—H17 | 0.9700 |
N1—C15 | 1.4812 (19) | C15—C16 | 1.500 (3) |
N2—C8 | 1.3903 (18) | C15—H4 | 0.9700 |
N2—C11 | 1.463 (2) | C15—H3 | 0.9700 |
N2—C14 | 1.476 (2) | C16—H7 | 0.9600 |
N3—C13 | 1.476 (2) | C16—H6 | 0.9600 |
N3—C12 | 1.484 (2) | C16—H5 | 0.9600 |
N3—H15 | 0.9000 | C5'—C4' | 1.379 (3) |
N3—H14 | 0.9000 | C5'—C6' | 1.382 (3) |
C3—C2 | 1.483 (2) | C5'—H4' | 0.9300 |
C2—C1 | 1.361 (2) | C6'—C1' | 1.386 (3) |
C2—C4 | 1.426 (2) | C6'—H5' | 0.9300 |
C1—H1 | 0.9300 | C1'—C2' | 1.398 (2) |
C10—C5 | 1.402 (2) | C1'—C7' | 1.493 (2) |
C10—C9 | 1.405 (2) | C2'—C3' | 1.387 (3) |
C9—C8 | 1.395 (2) | C4'—C3' | 1.354 (3) |
C9—H8 | 0.9300 | C4'—H3' | 0.9300 |
C8—C7 | 1.414 (2) | C3'—H2' | 0.9300 |
C11—C12 | 1.515 (2) | | |
| | | |
C3—O2—H2 | 108.0 (13) | C7—C6—C5 | 120.87 (14) |
H1A—O1S—H1B | 114 (3) | C7—C6—H9 | 119.6 |
C2'—O3'—H1' | 104.9 (16) | C5—C6—H9 | 119.6 |
C1—N1—C10 | 119.23 (13) | C6—C7—F1 | 117.43 (14) |
C1—N1—C15 | 118.55 (12) | C6—C7—C8 | 123.65 (14) |
C10—N1—C15 | 122.21 (12) | F1—C7—C8 | 118.87 (14) |
C8—N2—C11 | 118.27 (12) | N2—C14—C13 | 109.84 (14) |
C8—N2—C14 | 118.60 (12) | N2—C14—H18 | 109.7 |
C11—N2—C14 | 110.54 (13) | C13—C14—H18 | 109.7 |
C13—N3—C12 | 111.16 (13) | N2—C14—H19 | 109.7 |
C13—N3—H15 | 109.4 | C13—C14—H19 | 109.7 |
C12—N3—H15 | 109.4 | H18—C14—H19 | 108.2 |
C13—N3—H14 | 109.4 | N3—C13—C14 | 109.97 (14) |
C12—N3—H14 | 109.4 | N3—C13—H16 | 109.7 |
H15—N3—H14 | 108.0 | C14—C13—H16 | 109.7 |
O1—C3—O2 | 120.98 (16) | N3—C13—H17 | 109.7 |
O1—C3—C2 | 123.45 (16) | C14—C13—H17 | 109.7 |
O2—C3—C2 | 115.55 (15) | H16—C13—H17 | 108.2 |
C1—C2—C4 | 119.56 (14) | N1—C15—C16 | 111.80 (14) |
C1—C2—C3 | 117.94 (15) | N1—C15—H4 | 109.3 |
C4—C2—C3 | 122.41 (14) | C16—C15—H4 | 109.3 |
N1—C1—C2 | 124.95 (14) | N1—C15—H3 | 109.3 |
N1—C1—H1 | 117.5 | C16—C15—H3 | 109.3 |
C2—C1—H1 | 117.5 | H4—C15—H3 | 107.9 |
N1—C10—C5 | 118.62 (13) | C15—C16—H7 | 109.5 |
N1—C10—C9 | 121.15 (13) | C15—C16—H6 | 109.5 |
C5—C10—C9 | 120.20 (13) | H7—C16—H6 | 109.5 |
C8—C9—C10 | 121.96 (14) | C15—C16—H5 | 109.5 |
C8—C9—H8 | 119.0 | H7—C16—H5 | 109.5 |
C10—C9—H8 | 119.0 | H6—C16—H5 | 109.5 |
N2—C8—C9 | 122.61 (14) | C4'—C5'—C6' | 118.6 (2) |
N2—C8—C7 | 121.77 (13) | C4'—C5'—H4' | 120.7 |
C9—C8—C7 | 115.49 (14) | C6'—C5'—H4' | 120.7 |
N2—C11—C12 | 110.59 (13) | C5'—C6'—C1' | 121.4 (2) |
N2—C11—H11 | 109.5 | C5'—C6'—H5' | 119.3 |
C12—C11—H11 | 109.5 | C1'—C6'—H5' | 119.3 |
N2—C11—H10 | 109.5 | C6'—C1'—C2' | 118.57 (17) |
C12—C11—H10 | 109.5 | C6'—C1'—C7' | 120.57 (17) |
H11—C11—H10 | 108.1 | C2'—C1'—C7' | 120.84 (18) |
N3—C12—C11 | 112.33 (13) | O3'—C2'—C3' | 118.51 (19) |
N3—C12—H13 | 109.1 | O3'—C2'—C1' | 121.81 (16) |
C11—C12—H13 | 109.1 | C3'—C2'—C1' | 119.7 (2) |
N3—C12—H12 | 109.1 | O1'—C7'—O2' | 122.89 (16) |
C11—C12—H12 | 109.1 | O1'—C7'—C1' | 119.16 (17) |
H13—C12—H12 | 107.9 | O2'—C7'—C1' | 117.94 (17) |
O3—C4—C2 | 122.77 (14) | C3'—C4'—C5' | 121.5 (2) |
O3—C4—C5 | 121.69 (14) | C3'—C4'—H3' | 119.3 |
C2—C4—C5 | 115.54 (13) | C5'—C4'—H3' | 119.3 |
C10—C5—C6 | 117.79 (14) | C4'—C3'—C2' | 120.3 (2) |
C10—C5—C4 | 121.94 (13) | C4'—C3'—H2' | 119.8 |
C6—C5—C4 | 120.26 (14) | C2'—C3'—H2' | 119.8 |
| | | |
O1—C3—C2—C1 | 8.3 (2) | C2—C4—C5—C10 | 2.1 (2) |
O2—C3—C2—C1 | −170.36 (14) | O3—C4—C5—C6 | 2.1 (2) |
O1—C3—C2—C4 | −174.96 (16) | C2—C4—C5—C6 | −178.06 (14) |
O2—C3—C2—C4 | 6.4 (2) | C10—C5—C6—C7 | −1.7 (2) |
C10—N1—C1—C2 | 2.0 (2) | C4—C5—C6—C7 | 178.48 (14) |
C15—N1—C1—C2 | −178.85 (15) | C5—C6—C7—F1 | −175.05 (14) |
C4—C2—C1—N1 | 1.6 (2) | C5—C6—C7—C8 | 2.2 (2) |
C3—C2—C1—N1 | 178.50 (14) | N2—C8—C7—C6 | −176.70 (15) |
C1—N1—C10—C5 | −3.4 (2) | C9—C8—C7—C6 | −0.8 (2) |
C15—N1—C10—C5 | 177.49 (14) | N2—C8—C7—F1 | 0.5 (2) |
C1—N1—C10—C9 | 178.11 (13) | C9—C8—C7—F1 | 176.40 (14) |
C15—N1—C10—C9 | −1.0 (2) | C8—N2—C14—C13 | 157.90 (14) |
N1—C10—C9—C8 | 179.83 (14) | C11—N2—C14—C13 | −60.81 (19) |
C5—C10—C9—C8 | 1.4 (2) | C12—N3—C13—C14 | −55.73 (19) |
C11—N2—C8—C9 | −4.9 (2) | N2—C14—C13—N3 | 59.7 (2) |
C14—N2—C8—C9 | 133.47 (16) | C1—N1—C15—C16 | −93.40 (17) |
C11—N2—C8—C7 | 170.78 (15) | C10—N1—C15—C16 | 85.68 (18) |
C14—N2—C8—C7 | −50.9 (2) | C4'—C5'—C6'—C1' | 0.6 (3) |
C10—C9—C8—N2 | 174.89 (13) | C5'—C6'—C1'—C2' | −0.4 (3) |
C10—C9—C8—C7 | −1.0 (2) | C5'—C6'—C1'—C7' | −179.03 (18) |
C8—N2—C11—C12 | −161.49 (14) | C6'—C1'—C2'—O3' | 179.05 (17) |
C14—N2—C11—C12 | 57.07 (18) | C7'—C1'—C2'—O3' | −2.3 (3) |
C13—N3—C12—C11 | 52.96 (19) | C6'—C1'—C2'—C3' | −1.0 (3) |
N2—C11—C12—N3 | −53.34 (19) | C7'—C1'—C2'—C3' | 177.68 (16) |
C1—C2—C4—O3 | 176.24 (14) | C6'—C1'—C7'—O1' | 1.4 (3) |
C3—C2—C4—O3 | −0.5 (2) | C2'—C1'—C7'—O1' | −177.18 (15) |
C1—C2—C4—C5 | −3.6 (2) | C6'—C1'—C7'—O2' | −179.73 (17) |
C3—C2—C4—C5 | 179.71 (13) | C2'—C1'—C7'—O2' | 1.7 (2) |
N1—C10—C5—C6 | −178.50 (13) | C6'—C5'—C4'—C3' | 0.5 (3) |
C9—C10—C5—C6 | 0.0 (2) | C5'—C4'—C3'—C2' | −1.9 (3) |
N1—C10—C5—C4 | 1.3 (2) | O3'—C2'—C3'—C4' | −177.92 (19) |
C9—C10—C5—C4 | 179.79 (13) | C1'—C2'—C3'—C4' | 2.1 (3) |
O3—C4—C5—C10 | −177.68 (14) | | |
Crystal data top
C23H26FN3O7 | V = 3394.48 (14) Å3 |
Mr = 475.47 | Z = 6 |
Triclinic, P1 | F(000) = 1500.0 |
a = 7.3258 (2) Å | Dx = 1.396 Mg m−3 |
b = 19.8297 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
c = 23.9108 (5) Å | µ = 0.11 mm−1 |
α = 96.924 (1)° | T = 296 K |
β = 97.210 (1)° | Block, colorless |
γ = 96.143 (1)° | 0.60 × 0.15 × 0.08 mm |
Data collection top
CCD area detector diffractometer | 15579 independent reflections |
Radiation source: fine-focus sealed tube | 7689 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
phi and ω scans | θmax = 27.6°, θmin = 1.7° |
Absorption correction: empirical (using intensity measurements) SADABS | h = −9→9 |
Tmin = 0.938, Tmax = 0.991 | k = −25→25 |
49327 measured reflections | l = −31→31 |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H 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 parameters | Δρmax = 0.18 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
Crystal data top
C23H26FN3O7 | γ = 96.143 (1)° |
Mr = 475.47 | V = 3394.48 (14) Å3 |
Triclinic, P1 | Z = 6 |
a = 7.3258 (2) Å | Mo Kα radiation |
b = 19.8297 (4) Å | µ = 0.11 mm−1 |
c = 23.9108 (5) Å | T = 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 = 0.991 | Rint = 0.047 |
49327 measured reflections | |
Refinement top
R[F2 > 2σ(F2)] = 0.049 | 3 restraints |
wR(F2) = 0.122 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.18 e Å−3 |
15579 reflections | Δρmin = −0.19 e Å−3 |
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 | x | y | z | Uiso*/Ueq | |
F1A | 0.7955 (2) | 1.07985 (6) | 0.11286 (5) | 0.0629 (4) | |
F1B | 0.7742 (2) | 0.23097 (6) | 0.17775 (5) | 0.0674 (4) | |
F1C | 0.61707 (19) | 0.44309 (5) | 0.52686 (5) | 0.0591 (4) | |
O1S | 0.4439 (3) | 0.93045 (9) | 0.35161 (7) | 0.0573 (5) | |
O2A | 0.6976 (2) | 1.00321 (8) | −0.20252 (6) | 0.0585 (4) | |
H2 | 0.697 (4) | 1.0320 (11) | −0.1691 (8) | 0.088* | |
O2S | 0.2387 (3) | 0.41258 (9) | 0.97820 (7) | 0.0597 (5) | |
O1A | 0.7431 (3) | 0.89563 (9) | −0.22413 (7) | 0.0895 (7) | |
O3S | 0.9420 (3) | 0.75184 (9) | 0.30124 (8) | 0.0638 (5) | |
O3A | 0.7047 (2) | 1.05282 (7) | −0.09915 (6) | 0.0545 (4) | |
N3B | 0.8813 (3) | 0.44907 (10) | 0.07972 (7) | 0.0402 (4) | |
O3B | 0.9994 (2) | 0.25550 (7) | 0.38534 (6) | 0.0614 (5) | |
O1B | 1.0983 (3) | 0.41470 (9) | 0.51593 (7) | 0.0781 (6) | |
O1X | 0.38485 (19) | 0.59125 (7) | 0.01692 (5) | 0.0461 (4) | |
O3X | 0.6899 (2) | 0.64382 (8) | 0.28104 (6) | 0.0542 (4) | |
H37 | 0.770 (4) | 0.6763 (12) | 0.2844 (11) | 0.081* | |
O2X | 0.1774 (2) | 0.52359 (7) | 0.05002 (6) | 0.0509 (4) | |
O2C | 0.2724 (2) | 0.39749 (8) | 0.21771 (6) | 0.0583 (4) | |
H42 | 0.302 (4) | 0.4248 (12) | 0.2540 (11) | 0.087* | |
O1C | 0.2573 (2) | 0.28815 (8) | 0.18309 (6) | 0.0663 (5) | |
O3C | 0.3857 (2) | 0.43833 (7) | 0.32027 (6) | 0.0548 (4) | |
O2Y | 1.1302 (2) | 0.14711 (8) | 0.61848 (6) | 0.0560 (4) | |
O3Y | 0.6980 (2) | 0.03789 (7) | 0.37222 (6) | 0.0472 (4) | |
H61 | 0.607 (3) | 0.0013 (11) | 0.3662 (9) | 0.071* | |
O1Y | 0.9277 (2) | 0.06708 (7) | 0.63958 (5) | 0.0523 (4) | |
O2Z | 0.5014 (2) | 0.84186 (8) | 0.25919 (6) | 0.0592 (4) | |
O3Z | 0.0121 (2) | 0.69531 (7) | 0.03106 (6) | 0.0555 (4) | |
H66 | −0.067 (4) | 0.6616 (12) | 0.0297 (10) | 0.083* | |
O1Z | 0.3153 (2) | 0.76659 (7) | 0.29379 (6) | 0.0511 (4) | |
N3A | 0.8493 (2) | 0.91589 (9) | 0.25997 (7) | 0.0478 (5) | |
H14A | 0.9085 | 0.9194 | 0.2957 | 0.057* | |
H15A | 0.7401 | 0.8895 | 0.2579 | 0.057* | |
N2A | 0.8444 (2) | 0.95121 (8) | 0.14637 (6) | 0.0392 (4) | |
N1A | 0.7837 (2) | 0.86367 (8) | −0.05532 (6) | 0.0420 (4) | |
O2B | 1.0967 (3) | 0.30424 (9) | 0.48763 (7) | 0.0695 (5) | |
H20 | 1.079 (4) | 0.2755 (12) | 0.4556 (9) | 0.104* | |
N2B | 0.7197 (2) | 0.35753 (8) | 0.14918 (6) | 0.0407 (4) | |
N1B | 0.8951 (2) | 0.44633 (8) | 0.35144 (7) | 0.0388 (4) | |
N1C | 0.4645 (2) | 0.24137 (7) | 0.34275 (6) | 0.0348 (4) | |
N2C | 0.6529 (2) | 0.31159 (8) | 0.54633 (6) | 0.0396 (4) | |
N3C | 0.4594 (2) | 0.21423 (8) | 0.60513 (6) | 0.0408 (4) | |
H14C | 0.3626 | 0.1825 | 0.6061 | 0.049* | |
H15C | 0.5333 | 0.2189 | 0.6388 | 0.049* | |
C12A | 0.8158 (4) | 0.98485 (11) | 0.24622 (8) | 0.0579 (7) | |
H15 | 0.9326 | 1.0145 | 0.2515 | 0.069* | |
H16 | 0.7366 | 1.0046 | 0.2717 | 0.069* | |
C11A | 0.7250 (3) | 0.97978 (11) | 0.18559 (8) | 0.0511 (6) | |
H17 | 0.6072 | 0.9508 | 0.1805 | 0.061* | |
H9 | 0.7010 | 1.0249 | 0.1771 | 0.061* | |
C8A | 0.8067 (3) | 0.95979 (10) | 0.08890 (8) | 0.0353 (5) | |
C9A | 0.8022 (3) | 0.90672 (10) | 0.04483 (8) | 0.0382 (5) | |
H19 | 0.8151 | 0.8629 | 0.0536 | 0.046* | |
C10A | 0.7788 (3) | 0.91744 (9) | −0.01227 (8) | 0.0352 (5) | |
C5A | 0.7522 (3) | 0.98208 (10) | −0.02700 (8) | 0.0361 (5) | |
C4A | 0.7292 (3) | 0.99433 (10) | −0.08589 (8) | 0.0397 (5) | |
C2A | 0.7393 (3) | 0.93709 (10) | −0.12678 (8) | 0.0419 (5) | |
C3A | 0.7267 (3) | 0.94249 (13) | −0.18859 (9) | 0.0541 (6) | |
C15A | 0.8012 (4) | 0.79303 (10) | −0.04313 (9) | 0.0576 (7) | |
H6 | 0.8896 | 0.7945 | −0.0091 | 0.069* | |
H7 | 0.8484 | 0.7679 | −0.0744 | 0.069* | |
C16A | 0.6184 (4) | 0.75643 (12) | −0.03486 (12) | 0.0956 (10) | |
H4 | 0.5713 | 0.7813 | −0.0039 | 0.143* | |
H3 | 0.6350 | 0.7112 | −0.0263 | 0.143* | |
H5 | 0.5321 | 0.7533 | −0.0690 | 0.143* | |
C1A | 0.7636 (3) | 0.87525 (10) | −0.10978 (8) | 0.0466 (6) | |
H8 | 0.7665 | 0.8386 | −0.1377 | 0.056* | |
C13A | 0.9623 (3) | 0.88374 (11) | 0.21982 (8) | 0.0483 (6) | |
H14 | 0.9729 | 0.8372 | 0.2272 | 0.058* | |
H13 | 1.0861 | 0.9086 | 0.2263 | 0.058* | |
C14A | 0.8807 (3) | 0.88270 (10) | 0.15856 (8) | 0.0453 (5) | |
H12 | 0.9659 | 0.8655 | 0.1340 | 0.054* | |
H11 | 0.7658 | 0.8519 | 0.1504 | 0.054* | |
C7A | 0.7826 (3) | 1.02465 (10) | 0.07221 (8) | 0.0416 (5) | |
C6A | 0.7539 (3) | 1.03562 (10) | 0.01707 (8) | 0.0418 (5) | |
H18 | 0.7351 | 1.0791 | 0.0084 | 0.050* | |
C3B | 1.0677 (3) | 0.36715 (14) | 0.47835 (10) | 0.0535 (6) | |
C2B | 0.9971 (3) | 0.37282 (11) | 0.41794 (8) | 0.0414 (5) | |
C4B | 0.9691 (3) | 0.31477 (10) | 0.37511 (9) | 0.0410 (5) | |
C5B | 0.9022 (3) | 0.32714 (9) | 0.31833 (8) | 0.0364 (5) | |
C6B | 0.8707 (3) | 0.27313 (10) | 0.27308 (9) | 0.0438 (5) | |
H29 | 0.8910 | 0.2292 | 0.2799 | 0.053* | |
C7B | 0.8111 (3) | 0.28471 (10) | 0.21980 (9) | 0.0430 (5) | |
C8B | 0.7801 (3) | 0.35017 (10) | 0.20572 (8) | 0.0367 (5) | |
C11B | 0.8294 (3) | 0.33375 (10) | 0.10531 (8) | 0.0463 (6) | |
H35 | 0.7475 | 0.3176 | 0.0700 | 0.056* | |
H34 | 0.8906 | 0.2956 | 0.1168 | 0.056* | |
C12B | 0.9719 (3) | 0.38935 (10) | 0.09551 (8) | 0.0427 (5) | |
H36 | 1.0602 | 0.4031 | 0.1298 | 0.051* | |
H21 | 1.0389 | 0.3725 | 0.0653 | 0.051* | |
C10B | 0.8659 (3) | 0.39229 (9) | 0.30657 (8) | 0.0330 (5) | |
C1B | 0.9602 (3) | 0.43522 (11) | 0.40400 (8) | 0.0437 (5) | |
H22 | 0.9815 | 0.4723 | 0.4328 | 0.052* | |
C15B | 0.8701 (3) | 0.51756 (9) | 0.34208 (9) | 0.0497 (6) | |
H26 | 0.8508 | 0.5435 | 0.3775 | 0.060* | |
H27 | 0.7610 | 0.5172 | 0.3144 | 0.060* | |
C16B | 1.0380 (4) | 0.55186 (12) | 0.32087 (13) | 0.0881 (9) | |
H25 | 1.1461 | 0.5522 | 0.3482 | 0.132* | |
H24 | 1.0196 | 0.5981 | 0.3158 | 0.132* | |
H23 | 1.0547 | 0.5271 | 0.2852 | 0.132* | |
C9B | 0.8051 (3) | 0.40279 (9) | 0.25048 (8) | 0.0359 (5) | |
H28 | 0.7811 | 0.4463 | 0.2433 | 0.043* | |
C14B | 0.6382 (3) | 0.41886 (10) | 0.13656 (8) | 0.0440 (5) | |
H32 | 0.5770 | 0.4354 | 0.1683 | 0.053* | |
H33 | 0.5446 | 0.4069 | 0.1033 | 0.053* | |
C13B | 0.7786 (3) | 0.47590 (10) | 0.12564 (8) | 0.0423 (5) | |
H31 | 0.7157 | 0.5138 | 0.1143 | 0.051* | |
H30 | 0.8643 | 0.4924 | 0.1601 | 0.051* | |
C7X | 0.3180 (3) | 0.56731 (10) | 0.05772 (8) | 0.0352 (5) | |
C1X | 0.4142 (3) | 0.58990 (9) | 0.11700 (7) | 0.0313 (4) | |
C2X | 0.3723 (3) | 0.55389 (9) | 0.16120 (8) | 0.0386 (5) | |
H41 | 0.2803 | 0.5166 | 0.1539 | 0.046* | |
C3X | 0.4649 (3) | 0.57256 (10) | 0.21558 (8) | 0.0415 (5) | |
H40 | 0.4365 | 0.5476 | 0.2446 | 0.050* | |
C4X | 0.6000 (3) | 0.62839 (10) | 0.22693 (8) | 0.0377 (5) | |
C5X | 0.6410 (3) | 0.66594 (9) | 0.18382 (8) | 0.0366 (5) | |
H38 | 0.7303 | 0.7041 | 0.1916 | 0.044* | |
C6X | 0.5491 (3) | 0.64641 (9) | 0.12956 (8) | 0.0353 (5) | |
H39 | 0.5778 | 0.6715 | 0.1007 | 0.042* | |
C3C | 0.2952 (3) | 0.33294 (12) | 0.22322 (9) | 0.0459 (5) | |
C2C | 0.3684 (3) | 0.32204 (10) | 0.28185 (8) | 0.0363 (5) | |
C1C | 0.3980 (3) | 0.25718 (10) | 0.29165 (8) | 0.0384 (5) | |
H60 | 0.3705 | 0.2221 | 0.2612 | 0.046* | |
C10C | 0.5016 (3) | 0.29211 (9) | 0.38985 (8) | 0.0317 (4) | |
C9C | 0.5623 (3) | 0.27622 (9) | 0.44424 (8) | 0.0348 (5) | |
H53 | 0.5823 | 0.2314 | 0.4483 | 0.042* | |
C8C | 0.5931 (3) | 0.32498 (9) | 0.49173 (8) | 0.0339 (5) | |
C11C | 0.5491 (3) | 0.33348 (10) | 0.59265 (8) | 0.0485 (6) | |
H45 | 0.5009 | 0.3759 | 0.5860 | 0.058* | |
H46 | 0.6321 | 0.3420 | 0.6284 | 0.058* | |
C12C | 0.3911 (3) | 0.28006 (10) | 0.59678 (8) | 0.0459 (6) | |
H47 | 0.3278 | 0.2952 | 0.6284 | 0.055* | |
H48 | 0.3029 | 0.2741 | 0.5622 | 0.055* | |
C5C | 0.4741 (3) | 0.35960 (9) | 0.38255 (8) | 0.0339 (5) | |
C4C | 0.4074 (3) | 0.37672 (10) | 0.32706 (8) | 0.0379 (5) | |
C6C | 0.5134 (3) | 0.41005 (9) | 0.43020 (8) | 0.0390 (5) | |
H54 | 0.4995 | 0.4554 | 0.4262 | 0.047* | |
C7C | 0.5714 (3) | 0.39293 (9) | 0.48187 (8) | 0.0397 (5) | |
C14C | 0.7174 (3) | 0.24567 (10) | 0.55397 (8) | 0.0435 (5) | |
H52 | 0.8077 | 0.2516 | 0.5881 | 0.052* | |
H51 | 0.7794 | 0.2309 | 0.5219 | 0.052* | |
C13C | 0.5643 (3) | 0.19066 (10) | 0.55886 (8) | 0.0437 (5) | |
H49 | 0.4815 | 0.1801 | 0.5231 | 0.052* | |
H50 | 0.6165 | 0.1493 | 0.5669 | 0.052* | |
C15C | 0.4871 (3) | 0.16892 (9) | 0.34791 (8) | 0.0423 (5) | |
H58 | 0.5996 | 0.1671 | 0.3735 | 0.051* | |
H59 | 0.5001 | 0.1453 | 0.3109 | 0.051* | |
C16C | 0.3241 (4) | 0.13275 (10) | 0.37001 (10) | 0.0622 (7) | |
H57 | 0.3136 | 0.1549 | 0.4072 | 0.093* | |
H55 | 0.3426 | 0.0859 | 0.3721 | 0.093* | |
H56 | 0.2125 | 0.1345 | 0.3447 | 0.093* | |
C7Y | 0.9997 (3) | 0.09965 (10) | 0.60404 (8) | 0.0384 (5) | |
C1Y | 0.9214 (3) | 0.08205 (9) | 0.54257 (8) | 0.0322 (5) | |
C6Y | 0.7878 (3) | 0.02642 (9) | 0.52425 (8) | 0.0353 (5) | |
H62 | 0.7489 | −0.0010 | 0.5505 | 0.042* | |
C5Y | 0.7110 (3) | 0.01073 (9) | 0.46794 (8) | 0.0366 (5) | |
H63 | 0.6204 | −0.0267 | 0.4566 | 0.044* | |
C4Y | 0.7690 (3) | 0.05086 (9) | 0.42805 (8) | 0.0342 (5) | |
C2Y | 0.9784 (3) | 0.12140 (9) | 0.50220 (8) | 0.0380 (5) | |
H65 | 1.0697 | 0.1586 | 0.5135 | 0.046* | |
C3Y | 0.9027 (3) | 0.10658 (9) | 0.44579 (8) | 0.0394 (5) | |
H64 | 0.9416 | 0.1341 | 0.4196 | 0.047* | |
C7Z | 0.3736 (3) | 0.79272 (10) | 0.25281 (8) | 0.0393 (5) | |
C1Z | 0.2806 (3) | 0.76558 (9) | 0.19395 (8) | 0.0330 (5) | |
C2Z | 0.3154 (3) | 0.79869 (9) | 0.14779 (8) | 0.0404 (5) | |
H69 | 0.4015 | 0.8378 | 0.1535 | 0.048* | |
C3Z | 0.2257 (3) | 0.77513 (10) | 0.09373 (8) | 0.0426 (5) | |
H70 | 0.2499 | 0.7984 | 0.0634 | 0.051* | |
C4Z | 0.0996 (3) | 0.71671 (9) | 0.08486 (8) | 0.0362 (5) | |
C6Z | 0.1533 (3) | 0.70685 (9) | 0.18404 (8) | 0.0360 (5) | |
H67 | 0.1285 | 0.6835 | 0.2143 | 0.043* | |
C5Z | 0.0633 (3) | 0.68257 (9) | 0.13014 (8) | 0.0368 (5) | |
H68 | −0.0218 | 0.6432 | 0.1242 | 0.044* | |
H14B | 0.796 (3) | 0.4345 (10) | 0.0462 (9) | 0.052 (6)* | |
H15B | 0.971 (3) | 0.4808 (10) | 0.0721 (8) | 0.047 (6)* | |
H2B | 0.218 (4) | 0.4477 (13) | 0.9989 (11) | 0.080 (9)* | |
H2A | 0.360 (5) | 0.4091 (14) | 0.9835 (12) | 0.108 (12)* | |
H3A | 0.920 (4) | 0.7864 (10) | 0.3238 (9) | 0.078 (9)* | |
H3B | 1.061 (4) | 0.7537 (13) | 0.2991 (11) | 0.089 (10)* | |
H1A | 0.455 (4) | 0.9007 (13) | 0.3230 (11) | 0.089 (10)* | |
H1B | 0.320 (5) | 0.9350 (15) | 0.3499 (12) | 0.119 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F1A | 0.0962 (11) | 0.0471 (7) | 0.0435 (7) | 0.0130 (7) | 0.0104 (7) | −0.0055 (6) |
F1B | 0.1064 (12) | 0.0407 (7) | 0.0514 (8) | 0.0019 (7) | 0.0083 (8) | 0.0009 (6) |
F1C | 0.0921 (11) | 0.0382 (6) | 0.0436 (7) | 0.0070 (7) | 0.0042 (7) | −0.0021 (6) |
O1S | 0.0518 (12) | 0.0613 (11) | 0.0502 (11) | −0.0064 (10) | 0.0035 (9) | −0.0116 (8) |
O2A | 0.0585 (11) | 0.0766 (12) | 0.0440 (9) | 0.0067 (9) | 0.0033 (8) | 0.0278 (8) |
O2S | 0.0439 (12) | 0.0601 (11) | 0.0668 (12) | −0.0042 (10) | 0.0107 (9) | −0.0178 (9) |
O1A | 0.157 (2) | 0.0713 (12) | 0.0333 (9) | −0.0029 (12) | 0.0057 (11) | 0.0026 (9) |
O3S | 0.0543 (13) | 0.0644 (12) | 0.0636 (12) | −0.0106 (10) | 0.0136 (10) | −0.0169 (9) |
O3A | 0.0684 (12) | 0.0502 (9) | 0.0478 (9) | 0.0113 (8) | 0.0029 (8) | 0.0201 (7) |
N3B | 0.0370 (11) | 0.0538 (11) | 0.0277 (10) | −0.0042 (10) | 0.0003 (9) | 0.0102 (9) |
O3B | 0.0784 (13) | 0.0513 (9) | 0.0611 (10) | 0.0195 (9) | 0.0060 (9) | 0.0280 (8) |
O1B | 0.0996 (16) | 0.0926 (13) | 0.0394 (10) | 0.0176 (12) | −0.0063 (10) | 0.0099 (10) |
O1X | 0.0399 (9) | 0.0633 (9) | 0.0319 (8) | −0.0042 (8) | 0.0002 (7) | 0.0083 (7) |
O3X | 0.0616 (12) | 0.0602 (10) | 0.0330 (8) | −0.0071 (8) | −0.0068 (8) | 0.0016 (7) |
O2X | 0.0383 (9) | 0.0642 (9) | 0.0418 (9) | −0.0131 (8) | 0.0026 (7) | −0.0064 (7) |
O2C | 0.0677 (12) | 0.0632 (11) | 0.0458 (9) | 0.0117 (9) | −0.0035 (9) | 0.0238 (8) |
O1C | 0.0868 (14) | 0.0721 (11) | 0.0373 (9) | 0.0110 (10) | −0.0034 (9) | 0.0080 (8) |
O3C | 0.0730 (12) | 0.0447 (9) | 0.0501 (9) | 0.0166 (8) | 0.0020 (8) | 0.0185 (7) |
O2Y | 0.0407 (10) | 0.0722 (10) | 0.0446 (9) | −0.0166 (9) | 0.0030 (7) | −0.0106 (8) |
O3Y | 0.0554 (10) | 0.0541 (9) | 0.0288 (8) | −0.0006 (8) | 0.0005 (7) | 0.0040 (7) |
O1Y | 0.0475 (10) | 0.0735 (10) | 0.0317 (8) | −0.0075 (8) | 0.0003 (7) | 0.0094 (7) |
O2Z | 0.0451 (10) | 0.0720 (10) | 0.0494 (9) | −0.0182 (9) | 0.0034 (7) | −0.0105 (8) |
O3Z | 0.0661 (12) | 0.0570 (10) | 0.0348 (8) | −0.0077 (8) | −0.0099 (8) | 0.0039 (8) |
O1Z | 0.0474 (10) | 0.0686 (10) | 0.0321 (8) | −0.0038 (8) | −0.0035 (7) | 0.0057 (7) |
N3A | 0.0418 (11) | 0.0717 (12) | 0.0284 (9) | −0.0044 (10) | 0.0033 (8) | 0.0121 (9) |
N2A | 0.0401 (11) | 0.0525 (10) | 0.0274 (9) | 0.0137 (9) | 0.0056 (8) | 0.0067 (8) |
N1A | 0.0563 (12) | 0.0380 (9) | 0.0295 (9) | 0.0027 (9) | 0.0007 (8) | 0.0045 (8) |
O2B | 0.0798 (13) | 0.0786 (13) | 0.0549 (11) | 0.0207 (11) | −0.0036 (10) | 0.0322 (9) |
N2B | 0.0457 (11) | 0.0475 (10) | 0.0302 (9) | 0.0053 (9) | 0.0076 (8) | 0.0088 (8) |
N1B | 0.0444 (11) | 0.0401 (9) | 0.0332 (10) | 0.0084 (8) | 0.0043 (8) | 0.0094 (8) |
N1C | 0.0415 (11) | 0.0355 (9) | 0.0289 (9) | 0.0070 (8) | 0.0069 (8) | 0.0069 (7) |
N2C | 0.0457 (11) | 0.0440 (10) | 0.0299 (9) | 0.0048 (9) | 0.0047 (8) | 0.0091 (8) |
N3C | 0.0367 (11) | 0.0542 (11) | 0.0286 (9) | −0.0046 (9) | −0.0019 (8) | 0.0092 (8) |
C12A | 0.0705 (18) | 0.0692 (16) | 0.0358 (13) | 0.0102 (14) | 0.0159 (12) | 0.0045 (11) |
C11A | 0.0498 (15) | 0.0697 (15) | 0.0388 (13) | 0.0193 (13) | 0.0135 (11) | 0.0093 (11) |
C8A | 0.0316 (12) | 0.0450 (12) | 0.0296 (11) | 0.0044 (10) | 0.0022 (9) | 0.0083 (9) |
C9A | 0.0441 (14) | 0.0398 (11) | 0.0309 (11) | 0.0042 (10) | 0.0034 (10) | 0.0080 (9) |
C10A | 0.0351 (12) | 0.0376 (11) | 0.0321 (11) | 0.0015 (10) | 0.0041 (9) | 0.0054 (9) |
C5A | 0.0336 (12) | 0.0414 (11) | 0.0325 (11) | 0.0022 (10) | 0.0008 (9) | 0.0083 (9) |
C4A | 0.0383 (13) | 0.0440 (12) | 0.0371 (12) | −0.0004 (10) | 0.0027 (10) | 0.0138 (10) |
C2A | 0.0449 (14) | 0.0465 (12) | 0.0318 (11) | −0.0035 (11) | 0.0005 (10) | 0.0089 (10) |
C3A | 0.0599 (17) | 0.0619 (16) | 0.0376 (14) | −0.0058 (13) | 0.0003 (12) | 0.0137 (12) |
C15A | 0.093 (2) | 0.0394 (12) | 0.0417 (13) | 0.0164 (14) | 0.0039 (13) | 0.0069 (10) |
C16A | 0.107 (3) | 0.0622 (17) | 0.105 (2) | −0.0318 (17) | −0.0184 (19) | 0.0330 (16) |
C1A | 0.0564 (16) | 0.0477 (13) | 0.0321 (12) | −0.0015 (11) | 0.0027 (11) | 0.0013 (10) |
C13A | 0.0436 (14) | 0.0666 (14) | 0.0383 (12) | 0.0092 (12) | 0.0076 (11) | 0.0176 (11) |
C14A | 0.0500 (15) | 0.0560 (13) | 0.0331 (12) | 0.0145 (12) | 0.0062 (10) | 0.0110 (10) |
C7A | 0.0454 (14) | 0.0424 (12) | 0.0361 (12) | 0.0072 (11) | 0.0067 (10) | −0.0008 (10) |
C6A | 0.0445 (14) | 0.0405 (11) | 0.0420 (13) | 0.0077 (10) | 0.0052 (10) | 0.0111 (10) |
C3B | 0.0473 (15) | 0.0736 (17) | 0.0445 (15) | 0.0116 (14) | 0.0077 (12) | 0.0231 (13) |
C2B | 0.0351 (13) | 0.0557 (13) | 0.0369 (12) | 0.0095 (11) | 0.0052 (10) | 0.0165 (11) |
C4B | 0.0334 (13) | 0.0489 (13) | 0.0458 (13) | 0.0073 (11) | 0.0081 (10) | 0.0217 (11) |
C5B | 0.0341 (12) | 0.0387 (11) | 0.0396 (12) | 0.0052 (10) | 0.0086 (10) | 0.0133 (10) |
C6B | 0.0503 (15) | 0.0356 (11) | 0.0490 (14) | 0.0068 (11) | 0.0104 (11) | 0.0154 (10) |
C7B | 0.0521 (15) | 0.0349 (11) | 0.0420 (13) | 0.0015 (11) | 0.0110 (11) | 0.0040 (10) |
C8B | 0.0350 (13) | 0.0418 (12) | 0.0355 (12) | 0.0020 (10) | 0.0111 (10) | 0.0100 (9) |
C11B | 0.0587 (16) | 0.0482 (12) | 0.0313 (11) | 0.0043 (12) | 0.0095 (11) | 0.0011 (10) |
C12B | 0.0428 (14) | 0.0583 (13) | 0.0279 (11) | 0.0086 (12) | 0.0079 (10) | 0.0041 (10) |
C10B | 0.0286 (12) | 0.0374 (11) | 0.0349 (11) | 0.0033 (9) | 0.0089 (9) | 0.0092 (9) |
C1B | 0.0444 (14) | 0.0508 (13) | 0.0358 (12) | 0.0063 (11) | 0.0045 (10) | 0.0064 (10) |
C15B | 0.0653 (17) | 0.0370 (12) | 0.0450 (13) | 0.0137 (12) | −0.0030 (12) | 0.0034 (10) |
C16B | 0.074 (2) | 0.0508 (15) | 0.135 (3) | −0.0094 (15) | −0.0122 (18) | 0.0342 (16) |
C9B | 0.0376 (13) | 0.0384 (11) | 0.0354 (12) | 0.0055 (10) | 0.0096 (10) | 0.0141 (9) |
C14B | 0.0380 (13) | 0.0612 (14) | 0.0359 (12) | 0.0104 (12) | 0.0055 (10) | 0.0148 (10) |
C13B | 0.0481 (14) | 0.0470 (12) | 0.0348 (12) | 0.0083 (11) | 0.0092 (10) | 0.0116 (10) |
C7X | 0.0298 (12) | 0.0401 (11) | 0.0341 (12) | 0.0048 (10) | 0.0018 (9) | 0.0012 (9) |
C1X | 0.0276 (11) | 0.0337 (10) | 0.0315 (11) | 0.0041 (9) | 0.0042 (9) | 0.0001 (8) |
C2X | 0.0363 (13) | 0.0370 (11) | 0.0396 (12) | −0.0011 (10) | 0.0026 (10) | 0.0014 (9) |
C3X | 0.0479 (14) | 0.0421 (12) | 0.0333 (12) | −0.0009 (11) | 0.0029 (10) | 0.0094 (9) |
C4X | 0.0407 (13) | 0.0419 (11) | 0.0271 (11) | 0.0056 (11) | −0.0020 (9) | −0.0026 (9) |
C5X | 0.0360 (13) | 0.0345 (10) | 0.0359 (12) | −0.0020 (10) | 0.0042 (10) | −0.0014 (9) |
C6X | 0.0367 (12) | 0.0365 (11) | 0.0328 (11) | 0.0045 (10) | 0.0051 (9) | 0.0048 (9) |
C3C | 0.0425 (14) | 0.0565 (14) | 0.0427 (14) | 0.0062 (12) | 0.0092 (11) | 0.0198 (12) |
C2C | 0.0327 (12) | 0.0450 (12) | 0.0340 (11) | 0.0063 (10) | 0.0053 (9) | 0.0138 (10) |
C1C | 0.0383 (13) | 0.0466 (12) | 0.0311 (11) | 0.0049 (10) | 0.0074 (9) | 0.0061 (9) |
C10C | 0.0322 (12) | 0.0341 (10) | 0.0306 (11) | 0.0045 (9) | 0.0098 (9) | 0.0058 (9) |
C9C | 0.0408 (13) | 0.0326 (10) | 0.0347 (11) | 0.0090 (10) | 0.0105 (9) | 0.0101 (9) |
C8C | 0.0353 (12) | 0.0377 (11) | 0.0303 (11) | 0.0038 (10) | 0.0096 (9) | 0.0068 (9) |
C11C | 0.0696 (17) | 0.0460 (12) | 0.0281 (11) | 0.0027 (12) | 0.0087 (11) | 0.0000 (9) |
C12C | 0.0493 (15) | 0.0589 (14) | 0.0324 (12) | 0.0114 (12) | 0.0137 (10) | 0.0051 (10) |
C5C | 0.0349 (12) | 0.0369 (11) | 0.0338 (11) | 0.0107 (10) | 0.0091 (9) | 0.0102 (9) |
C4C | 0.0361 (13) | 0.0409 (12) | 0.0408 (12) | 0.0080 (10) | 0.0095 (10) | 0.0152 (10) |
C6C | 0.0471 (14) | 0.0321 (11) | 0.0410 (12) | 0.0110 (10) | 0.0103 (10) | 0.0084 (9) |
C7C | 0.0509 (14) | 0.0332 (11) | 0.0342 (12) | 0.0050 (10) | 0.0098 (10) | −0.0018 (9) |
C14C | 0.0413 (14) | 0.0558 (13) | 0.0380 (12) | 0.0110 (11) | 0.0067 (10) | 0.0188 (10) |
C13C | 0.0546 (15) | 0.0448 (12) | 0.0338 (12) | 0.0089 (11) | 0.0082 (11) | 0.0097 (9) |
C15C | 0.0589 (16) | 0.0341 (11) | 0.0362 (12) | 0.0124 (11) | 0.0091 (11) | 0.0052 (9) |
C16C | 0.0749 (19) | 0.0434 (13) | 0.0689 (17) | −0.0002 (13) | 0.0129 (14) | 0.0143 (12) |
C7Y | 0.0293 (12) | 0.0482 (12) | 0.0363 (12) | 0.0055 (11) | 0.0044 (10) | −0.0001 (10) |
C1Y | 0.0276 (11) | 0.0360 (11) | 0.0320 (11) | 0.0043 (9) | 0.0036 (9) | 0.0011 (9) |
C6Y | 0.0360 (12) | 0.0374 (11) | 0.0319 (11) | 0.0008 (10) | 0.0058 (9) | 0.0044 (9) |
C5Y | 0.0365 (12) | 0.0352 (10) | 0.0349 (12) | −0.0022 (10) | 0.0023 (9) | 0.0003 (9) |
C4Y | 0.0362 (12) | 0.0361 (11) | 0.0309 (11) | 0.0087 (10) | 0.0056 (9) | 0.0017 (9) |
C2Y | 0.0323 (12) | 0.0362 (11) | 0.0427 (12) | −0.0026 (10) | 0.0039 (10) | 0.0014 (9) |
C3Y | 0.0411 (13) | 0.0404 (11) | 0.0374 (12) | 0.0002 (10) | 0.0066 (10) | 0.0106 (9) |
C7Z | 0.0316 (13) | 0.0471 (12) | 0.0356 (12) | 0.0034 (11) | 0.0013 (10) | −0.0037 (10) |
C1Z | 0.0290 (12) | 0.0345 (10) | 0.0342 (11) | 0.0064 (9) | 0.0018 (9) | −0.0003 (9) |
C2Z | 0.0401 (13) | 0.0360 (11) | 0.0433 (13) | 0.0004 (10) | 0.0041 (10) | 0.0044 (10) |
C3Z | 0.0478 (14) | 0.0466 (12) | 0.0334 (12) | 0.0050 (11) | 0.0014 (10) | 0.0112 (10) |
C4Z | 0.0384 (13) | 0.0361 (11) | 0.0314 (11) | 0.0053 (10) | −0.0021 (9) | 0.0005 (9) |
C6Z | 0.0402 (13) | 0.0369 (11) | 0.0304 (11) | 0.0046 (10) | 0.0048 (9) | 0.0030 (9) |
C5Z | 0.0360 (12) | 0.0330 (10) | 0.0393 (12) | 0.0001 (10) | 0.0053 (10) | 0.0003 (9) |
Geometric parameters (Å, º) top
F1A—C7A | 1.360 (2) | C3B—C2B | 1.493 (3) |
F1B—C7B | 1.353 (2) | C2B—C1B | 1.365 (3) |
F1C—C7C | 1.356 (2) | C2B—C4B | 1.424 (3) |
O1S—H1A | 0.87 (3) | C4B—C5B | 1.443 (3) |
O1S—H1B | 0.92 (3) | C5B—C10B | 1.401 (2) |
O2A—C3A | 1.319 (3) | C5B—C6B | 1.406 (3) |
O2A—H2 | 0.925 (16) | C6B—C7B | 1.348 (3) |
O2S—H2B | 0.84 (2) | C6B—H29 | 0.9300 |
O2S—H2A | 0.89 (3) | C7B—C8B | 1.414 (3) |
O1A—C3A | 1.208 (2) | C8B—C9B | 1.381 (2) |
O3S—H3A | 0.861 (16) | C11B—C12B | 1.496 (3) |
O3S—H3B | 0.87 (3) | C11B—H35 | 0.9700 |
O3A—C4A | 1.264 (2) | C11B—H34 | 0.9700 |
N3B—C12B | 1.483 (2) | C12B—H36 | 0.9700 |
N3B—C13B | 1.486 (2) | C12B—H21 | 0.9700 |
N3B—H14B | 0.95 (2) | C10B—C9B | 1.406 (2) |
N3B—H15B | 0.91 (2) | C1B—H22 | 0.9300 |
O3B—C4B | 1.266 (2) | C15B—C16B | 1.514 (3) |
O1B—C3B | 1.203 (3) | C15B—H26 | 0.9700 |
O1X—C7X | 1.264 (2) | C15B—H27 | 0.9700 |
O3X—C4X | 1.360 (2) | C16B—H25 | 0.9600 |
O3X—H37 | 0.81 (2) | C16B—H24 | 0.9600 |
O2X—C7X | 1.253 (2) | C16B—H23 | 0.9600 |
O2C—C3C | 1.328 (2) | C9B—H28 | 0.9300 |
O2C—H42 | 0.95 (2) | C14B—C13B | 1.514 (3) |
O1C—C3C | 1.209 (2) | C14B—H32 | 0.9700 |
O3C—C4C | 1.276 (2) | C14B—H33 | 0.9700 |
O2Y—C7Y | 1.251 (2) | C13B—H31 | 0.9700 |
O3Y—C4Y | 1.354 (2) | C13B—H30 | 0.9700 |
O3Y—H61 | 0.92 (2) | C7X—C1X | 1.495 (3) |
O1Y—C7Y | 1.261 (2) | C1X—C6X | 1.389 (2) |
O2Z—C7Z | 1.258 (2) | C1X—C2X | 1.392 (2) |
O3Z—C4Z | 1.360 (2) | C2X—C3X | 1.377 (3) |
O3Z—H66 | 0.83 (3) | C2X—H41 | 0.9300 |
O1Z—C7Z | 1.262 (2) | C3X—C4X | 1.380 (3) |
N3A—C13A | 1.476 (2) | C3X—H40 | 0.9300 |
N3A—C12A | 1.482 (2) | C4X—C5X | 1.387 (2) |
N3A—H14A | 0.9000 | C5X—C6X | 1.375 (2) |
N3A—H15A | 0.9000 | C5X—H38 | 0.9300 |
N2A—C8A | 1.402 (2) | C6X—H39 | 0.9300 |
N2A—C11A | 1.467 (2) | C3C—C2C | 1.486 (3) |
N2A—C14A | 1.468 (2) | C2C—C1C | 1.370 (2) |
N1A—C1A | 1.342 (2) | C2C—C4C | 1.414 (3) |
N1A—C10A | 1.397 (2) | C1C—H60 | 0.9300 |
N1A—C15A | 1.480 (2) | C10C—C5C | 1.403 (2) |
O2B—C3B | 1.327 (3) | C10C—C9C | 1.404 (2) |
O2B—H20 | 0.884 (16) | C9C—C8C | 1.378 (2) |
N2B—C8B | 1.399 (2) | C9C—H53 | 0.9300 |
N2B—C14B | 1.458 (2) | C8C—C7C | 1.418 (2) |
N2B—C11B | 1.464 (2) | C11C—C12C | 1.504 (3) |
N1B—C1B | 1.340 (2) | C11C—H45 | 0.9700 |
N1B—C10B | 1.400 (2) | C11C—H46 | 0.9700 |
N1B—C15B | 1.483 (2) | C12C—H47 | 0.9700 |
N1C—C1C | 1.343 (2) | C12C—H48 | 0.9700 |
N1C—C10C | 1.395 (2) | C5C—C6C | 1.401 (2) |
N1C—C15C | 1.481 (2) | C5C—C4C | 1.448 (3) |
N2C—C8C | 1.390 (2) | C6C—C7C | 1.350 (3) |
N2C—C14C | 1.461 (2) | C6C—H54 | 0.9300 |
N2C—C11C | 1.470 (2) | C14C—C13C | 1.505 (3) |
N3C—C12C | 1.474 (2) | C14C—H52 | 0.9700 |
N3C—C13C | 1.483 (2) | C14C—H51 | 0.9700 |
N3C—H14C | 0.9000 | C13C—H49 | 0.9700 |
N3C—H15C | 0.9000 | C13C—H50 | 0.9700 |
C12A—C11A | 1.504 (3) | C15C—C16C | 1.512 (3) |
C12A—H15 | 0.9700 | C15C—H58 | 0.9700 |
C12A—H16 | 0.9700 | C15C—H59 | 0.9700 |
C11A—H17 | 0.9700 | C16C—H57 | 0.9600 |
C11A—H9 | 0.9700 | C16C—H55 | 0.9600 |
C8A—C9A | 1.391 (2) | C16C—H56 | 0.9600 |
C8A—C7A | 1.414 (3) | C7Y—C1Y | 1.494 (3) |
C9A—C10A | 1.399 (2) | C1Y—C6Y | 1.383 (3) |
C9A—H19 | 0.9300 | C1Y—C2Y | 1.389 (2) |
C10A—C5A | 1.397 (2) | C6Y—C5Y | 1.377 (2) |
C5A—C6A | 1.401 (3) | C6Y—H62 | 0.9300 |
C5A—C4A | 1.450 (3) | C5Y—C4Y | 1.391 (2) |
C4A—C2A | 1.421 (3) | C5Y—H63 | 0.9300 |
C2A—C1A | 1.360 (3) | C4Y—C3Y | 1.383 (3) |
C2A—C3A | 1.487 (3) | C2Y—C3Y | 1.377 (3) |
C15A—C16A | 1.501 (4) | C2Y—H65 | 0.9300 |
C15A—H6 | 0.9700 | C3Y—H64 | 0.9300 |
C15A—H7 | 0.9700 | C7Z—C1Z | 1.494 (3) |
C16A—H4 | 0.9600 | C1Z—C2Z | 1.387 (2) |
C16A—H3 | 0.9600 | C1Z—C6Z | 1.388 (3) |
C16A—H5 | 0.9600 | C2Z—C3Z | 1.377 (3) |
C1A—H8 | 0.9300 | C2Z—H69 | 0.9300 |
C13A—C14A | 1.508 (3) | C3Z—C4Z | 1.379 (3) |
C13A—H14 | 0.9700 | C3Z—H70 | 0.9300 |
C13A—H13 | 0.9700 | C4Z—C5Z | 1.383 (2) |
C14A—H12 | 0.9700 | C6Z—C5Z | 1.377 (3) |
C14A—H11 | 0.9700 | C6Z—H67 | 0.9300 |
C7A—C6A | 1.356 (3) | C5Z—H68 | 0.9300 |
C6A—H18 | 0.9300 | | |
| | | |
H1A—O1S—H1B | 107 (3) | N1B—C15B—H27 | 109.4 |
C3A—O2A—H2 | 107.4 (15) | C16B—C15B—H27 | 109.4 |
H2B—O2S—H2A | 109 (3) | H26—C15B—H27 | 108.0 |
H3A—O3S—H3B | 110 (2) | C15B—C16B—H25 | 109.5 |
C12B—N3B—C13B | 110.50 (15) | C15B—C16B—H24 | 109.5 |
C12B—N3B—H14B | 108.3 (12) | H25—C16B—H24 | 109.5 |
C13B—N3B—H14B | 108.7 (12) | C15B—C16B—H23 | 109.5 |
C12B—N3B—H15B | 107.4 (12) | H25—C16B—H23 | 109.5 |
C13B—N3B—H15B | 113.0 (12) | H24—C16B—H23 | 109.5 |
H14B—N3B—H15B | 108.8 (17) | C8B—C9B—C10B | 121.72 (17) |
C4X—O3X—H37 | 112.3 (18) | C8B—C9B—H28 | 119.1 |
C3C—O2C—H42 | 109.2 (15) | C10B—C9B—H28 | 119.1 |
C4Y—O3Y—H61 | 110.1 (14) | N2B—C14B—C13B | 113.45 (17) |
C4Z—O3Z—H66 | 112.0 (18) | N2B—C14B—H32 | 108.9 |
C13A—N3A—C12A | 110.30 (15) | C13B—C14B—H32 | 108.9 |
C13A—N3A—H14A | 109.6 | N2B—C14B—H33 | 108.9 |
C12A—N3A—H14A | 109.6 | C13B—C14B—H33 | 108.9 |
C13A—N3A—H15A | 109.6 | H32—C14B—H33 | 107.7 |
C12A—N3A—H15A | 109.6 | N3B—C13B—C14B | 108.80 (16) |
H14A—N3A—H15A | 108.1 | N3B—C13B—H31 | 109.9 |
C8A—N2A—C11A | 117.89 (16) | C14B—C13B—H31 | 109.9 |
C8A—N2A—C14A | 116.72 (15) | N3B—C13B—H30 | 109.9 |
C11A—N2A—C14A | 110.05 (15) | C14B—C13B—H30 | 109.9 |
C1A—N1A—C10A | 119.41 (16) | H31—C13B—H30 | 108.3 |
C1A—N1A—C15A | 118.47 (16) | O2X—C7X—O1X | 122.22 (18) |
C10A—N1A—C15A | 122.05 (15) | O2X—C7X—C1X | 118.81 (18) |
C3B—O2B—H20 | 111.6 (18) | O1X—C7X—C1X | 118.93 (18) |
C8B—N2B—C14B | 119.44 (15) | C6X—C1X—C2X | 118.06 (17) |
C8B—N2B—C11B | 118.55 (17) | C6X—C1X—C7X | 121.40 (17) |
C14B—N2B—C11B | 111.52 (15) | C2X—C1X—C7X | 120.53 (17) |
C1B—N1B—C10B | 119.82 (16) | C3X—C2X—C1X | 121.12 (18) |
C1B—N1B—C15B | 118.03 (17) | C3X—C2X—H41 | 119.4 |
C10B—N1B—C15B | 121.98 (15) | C1X—C2X—H41 | 119.4 |
C1C—N1C—C10C | 119.88 (15) | C2X—C3X—C4X | 119.79 (18) |
C1C—N1C—C15C | 118.37 (16) | C2X—C3X—H40 | 120.1 |
C10C—N1C—C15C | 121.68 (15) | C4X—C3X—H40 | 120.1 |
C8C—N2C—C14C | 119.24 (15) | O3X—C4X—C3X | 117.46 (18) |
C8C—N2C—C11C | 118.87 (17) | O3X—C4X—C5X | 122.45 (18) |
C14C—N2C—C11C | 110.05 (15) | C3X—C4X—C5X | 120.08 (17) |
C12C—N3C—C13C | 111.29 (14) | C6X—C5X—C4X | 119.63 (18) |
C12C—N3C—H14C | 109.4 | C6X—C5X—H38 | 120.2 |
C13C—N3C—H14C | 109.4 | C4X—C5X—H38 | 120.2 |
C12C—N3C—H15C | 109.4 | C5X—C6X—C1X | 121.29 (18) |
C13C—N3C—H15C | 109.4 | C5X—C6X—H39 | 119.4 |
H14C—N3C—H15C | 108.0 | C1X—C6X—H39 | 119.4 |
N3A—C12A—C11A | 109.92 (18) | O1C—C3C—O2C | 121.24 (19) |
N3A—C12A—H15 | 109.7 | O1C—C3C—C2C | 124.5 (2) |
C11A—C12A—H15 | 109.7 | O2C—C3C—C2C | 114.2 (2) |
N3A—C12A—H16 | 109.7 | C1C—C2C—C4C | 119.92 (17) |
C11A—C12A—H16 | 109.7 | C1C—C2C—C3C | 118.50 (19) |
H15—C12A—H16 | 108.2 | C4C—C2C—C3C | 121.57 (18) |
N2A—C11A—C12A | 110.52 (18) | N1C—C1C—C2C | 123.68 (18) |
N2A—C11A—H17 | 109.5 | N1C—C1C—H60 | 118.2 |
C12A—C11A—H17 | 109.5 | C2C—C1C—H60 | 118.2 |
N2A—C11A—H9 | 109.5 | N1C—C10C—C5C | 119.11 (16) |
C12A—C11A—H9 | 109.5 | N1C—C10C—C9C | 120.95 (16) |
H17—C11A—H9 | 108.1 | C5C—C10C—C9C | 119.92 (17) |
C9A—C8A—N2A | 122.67 (17) | C8C—C9C—C10C | 122.00 (17) |
C9A—C8A—C7A | 115.76 (17) | C8C—C9C—H53 | 119.0 |
N2A—C8A—C7A | 121.45 (17) | C10C—C9C—H53 | 119.0 |
C8A—C9A—C10A | 121.86 (17) | C9C—C8C—N2C | 123.98 (17) |
C8A—C9A—H19 | 119.1 | C9C—C8C—C7C | 115.96 (17) |
C10A—C9A—H19 | 119.1 | N2C—C8C—C7C | 119.95 (17) |
C5A—C10A—N1A | 119.08 (16) | N2C—C11C—C12C | 111.32 (16) |
C5A—C10A—C9A | 120.57 (17) | N2C—C11C—H45 | 109.4 |
N1A—C10A—C9A | 120.34 (17) | C12C—C11C—H45 | 109.4 |
C10A—C5A—C6A | 117.94 (17) | N2C—C11C—H46 | 109.4 |
C10A—C5A—C4A | 121.39 (17) | C12C—C11C—H46 | 109.4 |
C6A—C5A—C4A | 120.65 (17) | H45—C11C—H46 | 108.0 |
O3A—C4A—C2A | 122.96 (18) | N3C—C12C—C11C | 110.67 (17) |
O3A—C4A—C5A | 121.30 (18) | N3C—C12C—H47 | 109.5 |
C2A—C4A—C5A | 115.74 (17) | C11C—C12C—H47 | 109.5 |
C1A—C2A—C4A | 120.08 (18) | N3C—C12C—H48 | 109.5 |
C1A—C2A—C3A | 117.98 (19) | C11C—C12C—H48 | 109.5 |
C4A—C2A—C3A | 121.94 (19) | H47—C12C—H48 | 108.1 |
O1A—C3A—O2A | 121.4 (2) | C6C—C5C—C10C | 118.40 (17) |
O1A—C3A—C2A | 123.6 (2) | C6C—C5C—C4C | 120.83 (17) |
O2A—C3A—C2A | 115.1 (2) | C10C—C5C—C4C | 120.76 (17) |
N1A—C15A—C16A | 111.6 (2) | O3C—C4C—C2C | 122.69 (17) |
N1A—C15A—H6 | 109.3 | O3C—C4C—C5C | 120.71 (18) |
C16A—C15A—H6 | 109.3 | C2C—C4C—C5C | 116.59 (17) |
N1A—C15A—H7 | 109.3 | C7C—C6C—C5C | 120.05 (17) |
C16A—C15A—H7 | 109.3 | C7C—C6C—H54 | 120.0 |
H6—C15A—H7 | 108.0 | C5C—C6C—H54 | 120.0 |
C15A—C16A—H4 | 109.5 | C6C—C7C—F1C | 118.98 (17) |
C15A—C16A—H3 | 109.5 | C6C—C7C—C8C | 123.51 (18) |
H4—C16A—H3 | 109.5 | F1C—C7C—C8C | 117.48 (17) |
C15A—C16A—H5 | 109.5 | N2C—C14C—C13C | 113.52 (17) |
H4—C16A—H5 | 109.5 | N2C—C14C—H52 | 108.9 |
H3—C16A—H5 | 109.5 | C13C—C14C—H52 | 108.9 |
N1A—C1A—C2A | 124.28 (19) | N2C—C14C—H51 | 108.9 |
N1A—C1A—H8 | 117.9 | C13C—C14C—H51 | 108.9 |
C2A—C1A—H8 | 117.9 | H52—C14C—H51 | 107.7 |
N3A—C13A—C14A | 112.47 (18) | N3C—C13C—C14C | 109.75 (16) |
N3A—C13A—H14 | 109.1 | N3C—C13C—H49 | 109.7 |
C14A—C13A—H14 | 109.1 | C14C—C13C—H49 | 109.7 |
N3A—C13A—H13 | 109.1 | N3C—C13C—H50 | 109.7 |
C14A—C13A—H13 | 109.1 | C14C—C13C—H50 | 109.7 |
H14—C13A—H13 | 107.8 | H49—C13C—H50 | 108.2 |
N2A—C14A—C13A | 111.54 (16) | N1C—C15C—C16C | 111.93 (17) |
N2A—C14A—H12 | 109.3 | N1C—C15C—H58 | 109.2 |
C13A—C14A—H12 | 109.3 | C16C—C15C—H58 | 109.2 |
N2A—C14A—H11 | 109.3 | N1C—C15C—H59 | 109.2 |
C13A—C14A—H11 | 109.3 | C16C—C15C—H59 | 109.2 |
H12—C14A—H11 | 108.0 | H58—C15C—H59 | 107.9 |
C6A—C7A—F1A | 117.47 (17) | C15C—C16C—H57 | 109.5 |
C6A—C7A—C8A | 123.24 (18) | C15C—C16C—H55 | 109.5 |
F1A—C7A—C8A | 119.24 (17) | H57—C16C—H55 | 109.5 |
C7A—C6A—C5A | 120.58 (18) | C15C—C16C—H56 | 109.5 |
C7A—C6A—H18 | 119.7 | H57—C16C—H56 | 109.5 |
C5A—C6A—H18 | 119.7 | H55—C16C—H56 | 109.5 |
O1B—C3B—O2B | 121.8 (2) | O2Y—C7Y—O1Y | 122.51 (19) |
O1B—C3B—C2B | 124.1 (2) | O2Y—C7Y—C1Y | 119.06 (18) |
O2B—C3B—C2B | 114.1 (2) | O1Y—C7Y—C1Y | 118.40 (18) |
C1B—C2B—C4B | 119.93 (18) | C6Y—C1Y—C2Y | 117.90 (17) |
C1B—C2B—C3B | 118.8 (2) | C6Y—C1Y—C7Y | 120.85 (17) |
C4B—C2B—C3B | 121.28 (19) | C2Y—C1Y—C7Y | 121.24 (18) |
O3B—C4B—C2B | 123.01 (18) | C5Y—C6Y—C1Y | 121.41 (18) |
O3B—C4B—C5B | 121.09 (19) | C5Y—C6Y—H62 | 119.3 |
C2B—C4B—C5B | 115.90 (17) | C1Y—C6Y—H62 | 119.3 |
C10B—C5B—C6B | 118.14 (17) | C6Y—C5Y—C4Y | 119.98 (18) |
C10B—C5B—C4B | 121.66 (18) | C6Y—C5Y—H63 | 120.0 |
C6B—C5B—C4B | 120.20 (17) | C4Y—C5Y—H63 | 120.0 |
C7B—C6B—C5B | 120.37 (18) | O3Y—C4Y—C3Y | 118.34 (17) |
C7B—C6B—H29 | 119.8 | O3Y—C4Y—C5Y | 122.47 (18) |
C5B—C6B—H29 | 119.8 | C3Y—C4Y—C5Y | 119.19 (18) |
C6B—C7B—F1B | 118.72 (17) | C3Y—C2Y—C1Y | 121.44 (18) |
C6B—C7B—C8B | 123.28 (19) | C3Y—C2Y—H65 | 119.3 |
F1B—C7B—C8B | 117.98 (18) | C1Y—C2Y—H65 | 119.3 |
C9B—C8B—N2B | 124.24 (17) | C2Y—C3Y—C4Y | 120.06 (18) |
C9B—C8B—C7B | 116.31 (17) | C2Y—C3Y—H64 | 120.0 |
N2B—C8B—C7B | 119.39 (17) | C4Y—C3Y—H64 | 120.0 |
N2B—C11B—C12B | 111.72 (16) | O2Z—C7Z—O1Z | 123.31 (18) |
N2B—C11B—H35 | 109.3 | O2Z—C7Z—C1Z | 118.54 (19) |
C12B—C11B—H35 | 109.3 | O1Z—C7Z—C1Z | 118.10 (18) |
N2B—C11B—H34 | 109.3 | C2Z—C1Z—C6Z | 117.91 (17) |
C12B—C11B—H34 | 109.3 | C2Z—C1Z—C7Z | 121.39 (18) |
H35—C11B—H34 | 107.9 | C6Z—C1Z—C7Z | 120.68 (17) |
N3B—C12B—C11B | 110.03 (18) | C3Z—C2Z—C1Z | 121.63 (19) |
N3B—C12B—H36 | 109.7 | C3Z—C2Z—H69 | 119.2 |
C11B—C12B—H36 | 109.7 | C1Z—C2Z—H69 | 119.2 |
N3B—C12B—H21 | 109.7 | C2Z—C3Z—C4Z | 119.49 (18) |
C11B—C12B—H21 | 109.7 | C2Z—C3Z—H70 | 120.3 |
H36—C12B—H21 | 108.2 | C4Z—C3Z—H70 | 120.3 |
N1B—C10B—C5B | 118.62 (16) | O3Z—C4Z—C3Z | 117.93 (18) |
N1B—C10B—C9B | 121.28 (17) | O3Z—C4Z—C5Z | 122.10 (18) |
C5B—C10B—C9B | 120.09 (17) | C3Z—C4Z—C5Z | 119.96 (18) |
N1B—C1B—C2B | 124.05 (19) | C5Z—C6Z—C1Z | 121.02 (18) |
N1B—C1B—H22 | 118.0 | C5Z—C6Z—H67 | 119.5 |
C2B—C1B—H22 | 118.0 | C1Z—C6Z—H67 | 119.5 |
N1B—C15B—C16B | 110.99 (18) | C6Z—C5Z—C4Z | 119.98 (18) |
N1B—C15B—H26 | 109.4 | C6Z—C5Z—H68 | 120.0 |
C16B—C15B—H26 | 109.4 | C4Z—C5Z—H68 | 120.0 |
| | | |
C13A—N3A—C12A—C11A | 56.6 (2) | C8B—N2B—C14B—C13B | 91.2 (2) |
C8A—N2A—C11A—C12A | −163.13 (18) | C11B—N2B—C14B—C13B | −53.2 (2) |
C14A—N2A—C11A—C12A | 59.6 (2) | C12B—N3B—C13B—C14B | −57.3 (2) |
N3A—C12A—C11A—N2A | −60.5 (2) | N2B—C14B—C13B—N3B | 54.7 (2) |
C11A—N2A—C8A—C9A | −134.2 (2) | O2X—C7X—C1X—C6X | −168.34 (18) |
C14A—N2A—C8A—C9A | 0.3 (3) | O1X—C7X—C1X—C6X | 14.0 (3) |
C11A—N2A—C8A—C7A | 50.0 (3) | O2X—C7X—C1X—C2X | 12.7 (3) |
C14A—N2A—C8A—C7A | −175.53 (19) | O1X—C7X—C1X—C2X | −165.03 (18) |
N2A—C8A—C9A—C10A | −174.86 (18) | C6X—C1X—C2X—C3X | −1.6 (3) |
C7A—C8A—C9A—C10A | 1.2 (3) | C7X—C1X—C2X—C3X | 177.45 (18) |
C1A—N1A—C10A—C5A | 0.3 (3) | C1X—C2X—C3X—C4X | 0.9 (3) |
C15A—N1A—C10A—C5A | −176.6 (2) | C2X—C3X—C4X—O3X | −178.67 (18) |
C1A—N1A—C10A—C9A | −179.07 (19) | C2X—C3X—C4X—C5X | 0.6 (3) |
C15A—N1A—C10A—C9A | 4.0 (3) | O3X—C4X—C5X—C6X | 177.95 (18) |
C8A—C9A—C10A—C5A | −2.4 (3) | C3X—C4X—C5X—C6X | −1.3 (3) |
C8A—C9A—C10A—N1A | 176.96 (18) | C4X—C5X—C6X—C1X | 0.5 (3) |
N1A—C10A—C5A—C6A | −177.97 (18) | C2X—C1X—C6X—C5X | 0.9 (3) |
C9A—C10A—C5A—C6A | 1.4 (3) | C7X—C1X—C6X—C5X | −178.14 (18) |
N1A—C10A—C5A—C4A | 0.2 (3) | O1C—C3C—C2C—C1C | 0.8 (3) |
C9A—C10A—C5A—C4A | 179.52 (18) | O2C—C3C—C2C—C1C | −179.46 (18) |
C10A—C5A—C4A—O3A | 179.8 (2) | O1C—C3C—C2C—C4C | −179.1 (2) |
C6A—C5A—C4A—O3A | −2.1 (3) | O2C—C3C—C2C—C4C | 0.6 (3) |
C10A—C5A—C4A—C2A | −1.2 (3) | C10C—N1C—C1C—C2C | 2.1 (3) |
C6A—C5A—C4A—C2A | 176.87 (19) | C15C—N1C—C1C—C2C | 178.95 (18) |
O3A—C4A—C2A—C1A | −179.2 (2) | C4C—C2C—C1C—N1C | −0.4 (3) |
C5A—C4A—C2A—C1A | 1.9 (3) | C3C—C2C—C1C—N1C | 179.67 (19) |
O3A—C4A—C2A—C3A | 1.7 (3) | C1C—N1C—C10C—C5C | −2.1 (3) |
C5A—C4A—C2A—C3A | −177.22 (19) | C15C—N1C—C10C—C5C | −178.74 (18) |
C1A—C2A—C3A—O1A | −2.6 (4) | C1C—N1C—C10C—C9C | 176.77 (18) |
C4A—C2A—C3A—O1A | 176.6 (2) | C15C—N1C—C10C—C9C | 0.1 (3) |
C1A—C2A—C3A—O2A | 178.1 (2) | N1C—C10C—C9C—C8C | −177.52 (17) |
C4A—C2A—C3A—O2A | −2.8 (3) | C5C—C10C—C9C—C8C | 1.3 (3) |
C1A—N1A—C15A—C16A | −96.5 (2) | C10C—C9C—C8C—N2C | 179.93 (18) |
C10A—N1A—C15A—C16A | 80.4 (3) | C10C—C9C—C8C—C7C | −3.9 (3) |
C10A—N1A—C1A—C2A | 0.4 (3) | C14C—N2C—C8C—C9C | 10.7 (3) |
C15A—N1A—C1A—C2A | 177.5 (2) | C11C—N2C—C8C—C9C | −128.5 (2) |
C4A—C2A—C1A—N1A | −1.6 (3) | C14C—N2C—C8C—C7C | −165.28 (18) |
C3A—C2A—C1A—N1A | 177.6 (2) | C11C—N2C—C8C—C7C | 55.5 (3) |
C12A—N3A—C13A—C14A | −53.4 (2) | C8C—N2C—C11C—C12C | 86.9 (2) |
C8A—N2A—C14A—C13A | 166.66 (17) | C14C—N2C—C11C—C12C | −55.8 (2) |
C11A—N2A—C14A—C13A | −55.5 (2) | C13C—N3C—C12C—C11C | −56.7 (2) |
N3A—C13A—C14A—N2A | 53.2 (2) | N2C—C11C—C12C—N3C | 57.3 (2) |
C9A—C8A—C7A—C6A | 1.0 (3) | N1C—C10C—C5C—C6C | −179.49 (17) |
N2A—C8A—C7A—C6A | 177.06 (19) | C9C—C10C—C5C—C6C | 1.7 (3) |
C9A—C8A—C7A—F1A | −176.37 (18) | N1C—C10C—C5C—C4C | 0.3 (3) |
N2A—C8A—C7A—F1A | −0.3 (3) | C9C—C10C—C5C—C4C | −178.53 (18) |
F1A—C7A—C6A—C5A | 175.44 (18) | C1C—C2C—C4C—O3C | 178.71 (19) |
C8A—C7A—C6A—C5A | −1.9 (3) | C3C—C2C—C4C—O3C | −1.3 (3) |
C10A—C5A—C6A—C7A | 0.7 (3) | C1C—C2C—C4C—C5C | −1.4 (3) |
C4A—C5A—C6A—C7A | −177.45 (19) | C3C—C2C—C4C—C5C | 178.60 (18) |
O1B—C3B—C2B—C1B | −1.6 (4) | C6C—C5C—C4C—O3C | 1.1 (3) |
O2B—C3B—C2B—C1B | 179.0 (2) | C10C—C5C—C4C—O3C | −178.70 (18) |
O1B—C3B—C2B—C4B | 178.1 (2) | C6C—C5C—C4C—C2C | −178.85 (18) |
O2B—C3B—C2B—C4B | −1.3 (3) | C10C—C5C—C4C—C2C | 1.4 (3) |
C1B—C2B—C4B—O3B | −179.5 (2) | C10C—C5C—C6C—C7C | −1.7 (3) |
C3B—C2B—C4B—O3B | 0.9 (3) | C4C—C5C—C6C—C7C | 178.46 (19) |
C1B—C2B—C4B—C5B | 0.3 (3) | C5C—C6C—C7C—F1C | 176.88 (18) |
C3B—C2B—C4B—C5B | −179.39 (19) | C5C—C6C—C7C—C8C | −1.1 (3) |
O3B—C4B—C5B—C10B | 179.17 (19) | C9C—C8C—C7C—C6C | 3.9 (3) |
C2B—C4B—C5B—C10B | −0.6 (3) | N2C—C8C—C7C—C6C | −179.76 (19) |
O3B—C4B—C5B—C6B | −0.4 (3) | C9C—C8C—C7C—F1C | −174.10 (17) |
C2B—C4B—C5B—C6B | 179.83 (18) | N2C—C8C—C7C—F1C | 2.2 (3) |
C10B—C5B—C6B—C7B | 1.5 (3) | C8C—N2C—C14C—C13C | −87.1 (2) |
C4B—C5B—C6B—C7B | −178.9 (2) | C11C—N2C—C14C—C13C | 55.4 (2) |
C5B—C6B—C7B—F1B | −177.07 (18) | C12C—N3C—C13C—C14C | 54.6 (2) |
C5B—C6B—C7B—C8B | 1.1 (3) | N2C—C14C—C13C—N3C | −54.7 (2) |
C14B—N2B—C8B—C9B | −14.3 (3) | C1C—N1C—C15C—C16C | −97.0 (2) |
C11B—N2B—C8B—C9B | 127.6 (2) | C10C—N1C—C15C—C16C | 79.7 (2) |
C14B—N2B—C8B—C7B | 162.79 (18) | O2Y—C7Y—C1Y—C6Y | 174.64 (18) |
C11B—N2B—C8B—C7B | −55.3 (3) | O1Y—C7Y—C1Y—C6Y | −7.2 (3) |
C6B—C7B—C8B—C9B | −3.2 (3) | O2Y—C7Y—C1Y—C2Y | −6.3 (3) |
F1B—C7B—C8B—C9B | 175.00 (18) | O1Y—C7Y—C1Y—C2Y | 171.87 (18) |
C6B—C7B—C8B—N2B | 179.5 (2) | C2Y—C1Y—C6Y—C5Y | −0.9 (3) |
F1B—C7B—C8B—N2B | −2.3 (3) | C7Y—C1Y—C6Y—C5Y | 178.25 (17) |
C8B—N2B—C11B—C12B | −91.0 (2) | C1Y—C6Y—C5Y—C4Y | 0.6 (3) |
C14B—N2B—C11B—C12B | 53.7 (2) | C6Y—C5Y—C4Y—O3Y | −179.85 (18) |
C13B—N3B—C12B—C11B | 59.6 (2) | C6Y—C5Y—C4Y—C3Y | −0.5 (3) |
N2B—C11B—C12B—N3B | −57.2 (2) | C6Y—C1Y—C2Y—C3Y | 1.1 (3) |
C1B—N1B—C10B—C5B | 1.4 (3) | C7Y—C1Y—C2Y—C3Y | −178.03 (18) |
C15B—N1B—C10B—C5B | 176.48 (19) | C1Y—C2Y—C3Y—C4Y | −1.0 (3) |
C1B—N1B—C10B—C9B | −177.29 (19) | O3Y—C4Y—C3Y—C2Y | −179.91 (18) |
C15B—N1B—C10B—C9B | −2.2 (3) | C5Y—C4Y—C3Y—C2Y | 0.7 (3) |
C6B—C5B—C10B—N1B | 179.38 (17) | O2Z—C7Z—C1Z—C2Z | −8.4 (3) |
C4B—C5B—C10B—N1B | −0.2 (3) | O1Z—C7Z—C1Z—C2Z | 169.21 (18) |
C6B—C5B—C10B—C9B | −2.0 (3) | O2Z—C7Z—C1Z—C6Z | 172.90 (18) |
C4B—C5B—C10B—C9B | 178.46 (18) | O1Z—C7Z—C1Z—C6Z | −9.5 (3) |
C10B—N1B—C1B—C2B | −1.8 (3) | C6Z—C1Z—C2Z—C3Z | 0.9 (3) |
C15B—N1B—C1B—C2B | −177.1 (2) | C7Z—C1Z—C2Z—C3Z | −177.87 (19) |
C4B—C2B—C1B—N1B | 0.9 (3) | C1Z—C2Z—C3Z—C4Z | −0.8 (3) |
C3B—C2B—C1B—N1B | −179.42 (19) | C2Z—C3Z—C4Z—O3Z | 179.33 (18) |
C1B—N1B—C15B—C16B | 95.0 (2) | C2Z—C3Z—C4Z—C5Z | 0.4 (3) |
C10B—N1B—C15B—C16B | −80.2 (2) | C2Z—C1Z—C6Z—C5Z | −0.5 (3) |
N2B—C8B—C9B—C10B | 179.85 (18) | C7Z—C1Z—C6Z—C5Z | 178.22 (18) |
C7B—C8B—C9B—C10B | 2.7 (3) | C1Z—C6Z—C5Z—C4Z | 0.2 (3) |
N1B—C10B—C9B—C8B | 178.42 (17) | O3Z—C4Z—C5Z—C6Z | −178.97 (18) |
C5B—C10B—C9B—C8B | −0.2 (3) | C3Z—C4Z—C5Z—C6Z | −0.1 (3) |
Experimental details
| (20120152_0m) | (20120156_0m) | (20120175_0m) | (2013130_0m) |
Crystal data |
Chemical formula | C44H56F2N6O14 | C41H57F2N6O21 | C23H26FN3O7 | C21H30FN3O10S |
Mr | 930.95 | 1007.93 | 475.47 | 535.55 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 100 | 100 | 100 | 100 |
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), 90 | 89.118 (19), 81.880 (17), 74.64 (2) |
V (Å3) | 2255.11 (11) | 2204.38 (13) | 2202.83 (8) | 1155.6 (5) |
Z | 2 | 2 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.11 | 0.13 | 0.11 | 0.21 |
Crystal size (mm) | 0.31 × 0.23 × 0.15 | 0.21 × 0.08 × 0.05 | 0.42 × 0.32 × 0.21 | 0.21 × 0.15 × 0.13 |
|
Data collection |
Diffractometer | CCD 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 |
Rint | 0.030 | 0.059 | 0.034 | 0.101 |
(sin θ/λ)max (Å−1) | 0.595 | 0.595 | 0.595 | 0.595 |
|
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 reflections | 7942 | 7784 | 3883 | 4065 |
No. of parameters | 633 | 673 | 328 | 334 |
No. of restraints | 164 | 14 | 0 | 22 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.68, −0.19 | 0.41, −0.31 | 0.21, −0.25 | 0.41, −0.41 |
| (2013176_0ma) | (2013329_0m) | (mo_2014070_0m) |
Crystal data |
Chemical formula | C26H23FN3O10S | C23H26FN3O7 | C23H26FN3O7 |
Mr | 588.54 | 475.47 | 475.47 |
Crystal system, space group | Orthorhombic, Pbca | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 100 | 296 | 296 |
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, 90 | 91.100 (3), 97.543 (3), 109.906 (3) | 96.924 (1), 97.210 (1), 96.143 (1) |
V (Å3) | 5346.3 (3) | 1136.71 (10) | 3394.48 (14) |
Z | 8 | 2 | 6 |
Radiation type | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 0.19 | 0.11 | 0.11 |
Crystal size (mm) | 0.30 × 0.04 × 0.03 | 0.15 × 0.06 × 0.03 | 0.60 × 0.15 × 0.08 |
|
Data collection |
Diffractometer | CCD area detector diffractometer | CCD area detector diffractometer | CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) SADABS | Empirical (using intensity measurements) SADABS | Empirical (using intensity measurements) SADABS |
Tmin, Tmax | 0.948, 0.995 | 0.984, 0.997 | 0.938, 0.991 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 47387, 5987, 3739 | 17531, 5221, 2989 | 49327, 15579, 7689 |
Rint | 0.103 | 0.029 | 0.047 |
(sin θ/λ)max (Å−1) | 0.650 | 0.650 | 0.651 |
|
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 reflections | 5987 | 5221 | 15579 |
No. of parameters | 419 | 322 | 972 |
No. of restraints | 4 | 0 | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.43, −0.40 | 0.17, −0.20 | 0.18, −0.19 |
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