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In a search for new crystalline forms of linezolid with modified thermal properties five cocrystals of this wide range antibiotic with aromatic acids were obtained via mechanochemical grinding and analyzed with single crystal X-ray diffraction, solid-state NMR spectroscopy, powder X-ray diffraction and DSC measurements. The coformers used in this study were benzoic acid, p-hy­droxy­benzoic acid, protocatechuic acid, γ-resorcylic acid and gallic acid. In each of the cocrystals distinct structural features have been found, including a variable amount of water and different heterosynthons, indicating that there is more than one type of intermolecular interaction preferred by the linezolid molecule. Basing on the frequency of the observed supramolecular synthons, the proposed hierarchy of the hydrogen-bond acceptor sites of linezolid (LIN) is C=Oamide > C=Ooxazolidone > C—O—Cmorpholine > C—N—Cmorpholine > C—O—Coxazolidone. In addition, aromatic–aromatic interactions were found to be important in the stabilization of the analyzed structures. The obtained cocrystals show modified thermal properties, with four of them having melting points lower than the temperature of the phase transition from linezolid form II to linezolid form III. Such a change in this physicochemical property allows for the future application of melting-based techniques of introducing linezolid into drug delivery systems. In addition a change in water solubility of linezolid upon cocrystalization was evaluated, but only in the case of the cocrystal with protocatechuic acid was there a significant (43%) improvement in solubility in comparison with linezolid.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520620010896/xk5072sup1.cif
Contains datablocks LIN:BA, LIN:PHBA:H2O, LIN:2,6-DHBA, LIN:3,4-DHBA:H2O, LIN:GA:H2O

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_BAsup2.hkl
Contains datablock LIN:BA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_PHBA_H2Osup3.hkl
Contains datablock LIN:PHBA:H2O

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_26DHBAsup4.hkl
Contains datablock LIN:2,6DHBA

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_34DHBA_H2Osup5.hkl
Contains datablock LIN:3,4-DHBA:H2O

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_GA_H2Osup6.hkl
Contains datablock LIN:GA:H2O

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520620010896/xk5072sup7.pdf
Supplementary material

CCDC references: 1993998; 1993999; 1994000; 1994001; 1997194

Computing details top

Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for LIN:BA, LIN:2,6-DHBA, LIN:3,4-DHBA:H2O, LIN:GA:H2O; CrysAlis PRO 1.171.41.56a (Rigaku OD, 2020) for LIN:PHBA:H2O. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for LIN:BA, LIN:2,6-DHBA, LIN:3,4-DHBA:H2O, LIN:GA:H2O; CrysAlis PRO 1.171.41.56a (Rigaku OD, 2020) for LIN:PHBA:H2O. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) for LIN:BA, LIN:2,6-DHBA, LIN:3,4-DHBA:H2O, LIN:GA:H2O; CrysAlis PRO 1.171.41.56a (Rigaku OD, 2020) for LIN:PHBA:H2O. Program(s) used to solve structure: SHELXS (Sheldrick, 2008) for LIN:BA, LIN:2,6-DHBA, LIN:3,4-DHBA:H2O, LIN:GA:H2O. For all structures, program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).

(LIN:BA) top
Crystal data top
C16H20FN3O4·C7H6O2F(000) = 484
Mr = 459.47Dx = 1.344 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 6.49617 (9) ÅCell parameters from 12111 reflections
b = 7.41888 (18) Åθ = 3.7–74.0°
c = 23.5870 (4) ŵ = 0.87 mm1
β = 92.9418 (13)°T = 293 K
V = 1135.26 (4) Å3Plate
Z = 20.63 × 0.40 × 0.10 mm
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
4213 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source4032 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.048
Detector resolution: 4.1685 pixels mm-1θmax = 74.6°, θmin = 3.8°
ω scansh = 88
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 79
Tmin = 0.211, Tmax = 1.000l = 2929
18906 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.060P)2 + 0.1176P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.037(Δ/σ)max < 0.001
wR(F2) = 0.103Δρmax = 0.18 e Å3
S = 1.03Δρmin = 0.15 e Å3
4213 reflectionsExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
301 parametersExtinction coefficient: 0.0069 (9)
1 restraintAbsolute structure: Flack x determined using 1576 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (9)
Hydrogen site location: inferred from neighbouring sites
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.8098 (2)0.0263 (3)0.37441 (6)0.0757 (6)
O11.1815 (3)0.1503 (3)0.03789 (7)0.0567 (5)
O20.8084 (2)0.0386 (3)0.09854 (6)0.0557 (5)
O30.6319 (2)0.0236 (4)0.17727 (7)0.0723 (6)
O41.3193 (3)0.2396 (3)0.52246 (7)0.0611 (5)
N11.1857 (3)0.0958 (3)0.41515 (7)0.0469 (4)
N20.9891 (2)0.0082 (3)0.18053 (7)0.0458 (4)
N31.2685 (3)0.2661 (3)0.04742 (8)0.0512 (5)
H31.3650810.3091320.0697740.061*
C11.5239 (4)0.2683 (4)0.02290 (12)0.0583 (6)
H1A1.5921070.1597870.0337330.087*
H1B1.6009580.3237600.0082430.087*
H1C1.5146790.3499200.0545110.087*
C21.3119 (3)0.2239 (3)0.00528 (9)0.0463 (5)
C31.0648 (3)0.2426 (4)0.06899 (10)0.0538 (6)
H3A0.9619500.2823150.0404160.065*
H3B1.0527050.3178860.1022860.065*
C41.0218 (3)0.0495 (4)0.08447 (8)0.0474 (5)
H41.0469020.0299330.0523450.057*
C51.1409 (3)0.0176 (4)0.13777 (9)0.0521 (6)
H5A1.1788840.1434480.1344090.063*
H5B1.2638900.0537140.1461200.063*
C60.7953 (3)0.0230 (4)0.15563 (9)0.0497 (6)
C71.0362 (3)0.0221 (4)0.23911 (8)0.0427 (5)
C80.8930 (3)0.0147 (4)0.27972 (9)0.0499 (6)
H80.7623220.0578860.2690890.060*
C90.9505 (3)0.0146 (4)0.33572 (9)0.0493 (5)
C101.1416 (3)0.0778 (3)0.35581 (9)0.0438 (5)
C111.2807 (3)0.1108 (4)0.31413 (10)0.0516 (6)
H111.4119430.1524540.3249720.062*
C121.2303 (3)0.0837 (4)0.25703 (9)0.0520 (6)
H121.3275980.1069690.2304050.062*
C131.0720 (4)0.2387 (4)0.44223 (9)0.0554 (6)
H13A1.1176010.3551030.4289540.066*
H13B0.9260580.2268630.4320190.066*
C141.1067 (4)0.2279 (4)0.50611 (10)0.0563 (6)
H14A1.0520140.1149040.5195380.068*
H14B1.0332640.3253960.5235990.068*
C151.4274 (4)0.0981 (5)0.49661 (11)0.0637 (7)
H15A1.5724220.1054620.5083960.076*
H15B1.3756180.0168300.5093940.076*
C161.4041 (3)0.1069 (5)0.43263 (10)0.0562 (6)
H16A1.4782400.0078490.4162080.067*
H16B1.4613090.2190070.4193270.067*
O50.4790 (4)0.4826 (5)0.13067 (9)0.0963 (9)
O60.7952 (3)0.5871 (4)0.14655 (8)0.0734 (6)
H60.7869680.6007160.1120090.110*
C200.6229 (5)0.5174 (4)0.16323 (11)0.0630 (7)
C210.6165 (5)0.4860 (4)0.22522 (11)0.0655 (7)
C220.4394 (7)0.4130 (6)0.24595 (16)0.0864 (10)
H220.3266940.3878480.2213030.104*
C230.4299 (10)0.3773 (7)0.30342 (18)0.1100 (16)
H230.3106100.3284860.3173160.132*
C240.5939 (12)0.4133 (7)0.33940 (16)0.120 (2)
H240.5878670.3866740.3778070.144*
C250.7684 (11)0.4886 (7)0.31953 (16)0.1200 (19)
H250.8787410.5154930.3447950.144*
C260.7830 (7)0.5258 (6)0.26179 (14)0.0896 (11)
H260.9021810.5761400.2483210.108*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0516 (7)0.1330 (17)0.0441 (7)0.0246 (10)0.0176 (6)0.0012 (9)
O10.0538 (8)0.0702 (12)0.0460 (8)0.0139 (8)0.0027 (6)0.0036 (8)
O20.0358 (7)0.0908 (14)0.0403 (7)0.0044 (8)0.0010 (5)0.0012 (8)
O30.0330 (7)0.130 (2)0.0546 (9)0.0008 (10)0.0070 (6)0.0036 (11)
O40.0702 (10)0.0698 (13)0.0430 (8)0.0009 (9)0.0003 (7)0.0064 (8)
N10.0435 (8)0.0593 (12)0.0385 (8)0.0043 (9)0.0063 (7)0.0049 (9)
N20.0327 (7)0.0681 (13)0.0370 (8)0.0015 (8)0.0070 (6)0.0020 (8)
N30.0461 (9)0.0626 (14)0.0447 (9)0.0086 (9)0.0002 (7)0.0039 (9)
C10.0481 (12)0.0639 (17)0.0635 (13)0.0064 (12)0.0083 (10)0.0016 (12)
C20.0465 (11)0.0468 (13)0.0457 (10)0.0027 (9)0.0023 (8)0.0023 (9)
C30.0468 (11)0.0682 (17)0.0468 (11)0.0034 (11)0.0062 (9)0.0015 (11)
C40.0384 (9)0.0675 (16)0.0368 (9)0.0014 (10)0.0056 (7)0.0028 (10)
C50.0375 (9)0.0789 (18)0.0406 (10)0.0057 (10)0.0095 (8)0.0043 (11)
C60.0358 (9)0.0719 (17)0.0416 (10)0.0028 (11)0.0041 (7)0.0003 (11)
C70.0354 (8)0.0558 (14)0.0374 (9)0.0014 (8)0.0065 (7)0.0024 (9)
C80.0371 (9)0.0703 (17)0.0430 (10)0.0063 (10)0.0085 (8)0.0008 (11)
C90.0387 (9)0.0685 (16)0.0418 (10)0.0028 (10)0.0132 (8)0.0017 (10)
C100.0406 (9)0.0518 (14)0.0397 (10)0.0009 (9)0.0075 (7)0.0041 (9)
C110.0387 (10)0.0724 (17)0.0442 (11)0.0082 (11)0.0072 (8)0.0084 (11)
C120.0398 (10)0.0750 (17)0.0419 (10)0.0084 (11)0.0105 (8)0.0052 (11)
C130.0604 (13)0.0628 (17)0.0433 (11)0.0144 (12)0.0052 (9)0.0059 (11)
C140.0662 (14)0.0600 (16)0.0433 (11)0.0075 (13)0.0091 (10)0.0046 (11)
C150.0580 (13)0.085 (2)0.0475 (12)0.0125 (14)0.0032 (10)0.0046 (14)
C160.0454 (11)0.0777 (19)0.0455 (11)0.0053 (12)0.0033 (8)0.0066 (12)
O50.1120 (18)0.121 (2)0.0533 (10)0.0467 (17)0.0176 (11)0.0036 (13)
O60.0747 (12)0.0943 (17)0.0505 (10)0.0001 (11)0.0024 (8)0.0011 (11)
C200.0835 (17)0.0590 (17)0.0459 (12)0.0054 (15)0.0041 (11)0.0053 (12)
C210.096 (2)0.0550 (17)0.0450 (12)0.0017 (15)0.0025 (12)0.0045 (11)
C220.116 (3)0.078 (2)0.0666 (18)0.005 (2)0.0136 (18)0.0042 (18)
C230.176 (5)0.089 (3)0.068 (2)0.006 (3)0.039 (3)0.008 (2)
C240.233 (7)0.078 (3)0.0503 (18)0.018 (4)0.015 (3)0.0064 (19)
C250.206 (6)0.094 (3)0.0548 (18)0.005 (4)0.042 (3)0.008 (2)
C260.133 (3)0.076 (2)0.0565 (16)0.011 (2)0.0250 (17)0.0026 (16)
Geometric parameters (Å, º) top
F1—C91.359 (2)C7—C81.396 (3)
O1—C21.241 (3)C7—C121.386 (3)
O2—C41.444 (2)C8—C91.372 (3)
O2—C61.358 (3)C9—C101.387 (3)
O3—C61.202 (3)C10—C111.391 (3)
O4—C141.417 (3)C11—C121.384 (3)
O4—C151.418 (4)C13—C141.514 (3)
N1—C101.420 (3)C15—C161.510 (3)
N1—C131.458 (3)O5—C201.207 (4)
N1—C161.459 (3)O6—C201.312 (4)
N2—C51.459 (2)C20—C211.483 (4)
N2—C61.366 (3)C21—C221.384 (5)
N2—C71.418 (3)C21—C261.380 (5)
N3—C21.326 (3)C22—C231.386 (5)
N3—C31.453 (3)C23—C241.354 (8)
C1—C21.495 (3)C24—C251.368 (8)
C3—C41.508 (4)C25—C261.398 (5)
C4—C51.525 (3)
C6—O2—C4110.02 (15)F1—C9—C8116.88 (19)
C14—O4—C15109.6 (2)F1—C9—C10117.86 (19)
C10—N1—C13114.77 (18)C8—C9—C10125.24 (18)
C10—N1—C16115.33 (16)C9—C10—N1119.99 (18)
C13—N1—C16110.0 (2)C9—C10—C11114.88 (19)
C6—N2—C5110.73 (16)C11—C10—N1125.05 (19)
C6—N2—C7125.44 (16)C12—C11—C10122.1 (2)
C7—N2—C5122.21 (17)C11—C12—C7120.72 (19)
C2—N3—C3122.78 (19)N1—C13—C14110.1 (2)
O1—C2—N3120.9 (2)O4—C14—C13111.1 (2)
O1—C2—C1122.3 (2)O4—C15—C16111.8 (2)
N3—C2—C1116.8 (2)N1—C16—C15109.04 (19)
N3—C3—C4112.4 (2)O5—C20—O6122.6 (3)
O2—C4—C3107.5 (2)O5—C20—C21122.3 (3)
O2—C4—C5104.15 (16)O6—C20—C21115.1 (2)
C3—C4—C5114.7 (2)C22—C21—C20118.4 (3)
N2—C5—C4101.23 (16)C26—C21—C20121.5 (3)
O2—C6—N2109.25 (16)C26—C21—C22120.2 (3)
O3—C6—O2121.50 (19)C21—C22—C23120.0 (4)
O3—C6—N2129.2 (2)C24—C23—C22120.1 (5)
C8—C7—N2121.30 (19)C23—C24—C25120.3 (4)
C12—C7—N2119.80 (17)C24—C25—C26120.9 (4)
C12—C7—C8118.87 (19)C21—C26—C25118.4 (4)
C9—C8—C7118.15 (19)
(LIN:PHBA:H2O) top
Crystal data top
C16H20FN3O4·C7H6O3·H2ODx = 1.401 Mg m3
Mr = 492.47Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 4747 reflections
a = 6.428 (3) Åθ = 3.3–73.9°
b = 6.987 (3) ŵ = 0.95 mm1
c = 52.001 (9) ÅT = 100 K
V = 2335.5 (15) Å3Needle, colourless
Z = 40.5 × 0.15 × 0.09 mm
F(000) = 1036
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
8325 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source6511 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.187
Detector resolution: 8.3370 pixels mm-1θmax = 67.5°, θmin = 3.4°
ω scansh = 77
Absorption correction: multi-scan
CrysAlisPro 1.171.41.56a (Rigaku Oxford Diffraction, 2020) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 88
Tmin = 0.809, Tmax = 1.000l = 6162
8325 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.143(Δ/σ)max = 0.002
wR(F2) = 0.397Δρmax = 1.48 e Å3
S = 1.65Δρmin = 0.82 e Å3
8325 reflectionsExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
320 parametersExtinction coefficient: 0.031 (10)
0 restraintsAbsolute structure: Classical Flack method preferred over Parsons because s.u. lower.
Hydrogen site location: mixedAbsolute structure parameter: 1.5 (6)
Special details top

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

Refinement. Refined as a 4-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F11.7514 (13)1.5372 (16)1.07772 (15)0.058 (3)
O11.3158 (12)1.6111 (14)1.26644 (15)0.036 (2)
O21.7047 (12)1.4987 (14)1.20233 (15)0.0351 (19)
O31.8963 (12)1.503 (2)1.16661 (16)0.046 (3)
O41.174 (2)1.482 (3)1.0103 (2)0.079 (5)
N11.3736 (18)1.426 (2)1.0588 (2)0.044 (3)
N21.5314 (13)1.4895 (18)1.16499 (18)0.035 (2)
N31.2295 (16)1.7311 (17)1.22775 (18)0.035 (2)
H31.1300191.7703471.2173870.042*
C10.9664 (18)1.7376 (19)1.2609 (2)0.036 (3)
H1A0.9736221.8308011.2749240.054*
H1B0.8996871.6201271.2670310.054*
H1C0.8849101.7912931.2466630.054*
C21.1834 (17)1.6924 (18)1.2516 (2)0.032 (2)
C31.4407 (18)1.7118 (19)1.2176 (2)0.034 (3)
H3A1.5416461.7497681.2310170.041*
H3B1.4581351.7999691.2028180.041*
C41.4879 (16)1.511 (2)1.2090 (2)0.037 (3)
H41.4575031.4200621.2233560.044*
C51.3735 (15)1.444 (2)1.1846 (2)0.036 (3)
H5A1.3420131.3057171.1851450.043*
H5B1.2433421.5171061.1817950.043*
C61.7275 (16)1.4946 (16)1.1772 (2)0.032 (2)
C71.4954 (15)1.4745 (19)1.1393 (2)0.0341 (19)
C81.6487 (15)1.5209 (19)1.1204 (2)0.0341 (19)
H81.7828211.5643931.1254020.041*
C91.5994 (18)1.502 (2)1.0958 (2)0.041 (3)
C101.4046 (18)1.439 (2)1.0856 (2)0.041 (3)
C111.256 (2)1.396 (2)1.1047 (2)0.040 (3)
H111.1212881.3565071.0995090.049*
C121.299 (2)1.407 (2)1.1304 (2)0.043 (3)
H121.1962681.3699061.1425000.051*
C131.380 (3)1.612 (3)1.0453 (3)0.057 (4)
H13A1.2636021.6925531.0515470.069*
H13B1.5115521.6776821.0495390.069*
C141.363 (4)1.590 (3)1.0175 (3)0.070 (5)
H14A1.4873641.5213521.0109420.084*
H14B1.3597761.7179251.0093200.084*
C151.159 (3)1.310 (4)1.0237 (3)0.073 (6)
H15A1.2707861.2233241.0176400.088*
H15B1.0242371.2491691.0195780.088*
C161.176 (3)1.331 (3)1.0521 (3)0.055 (4)
H16A1.0579531.4071631.0586030.066*
H16B1.1710491.2029881.0602540.066*
O51.0381 (15)1.9498 (17)1.18910 (17)0.048 (2)
O60.7177 (14)2.0584 (16)1.18422 (15)0.043 (2)
H60.7192562.0503301.2003320.065*
O70.9517 (19)1.9275 (19)1.06833 (17)0.053 (3)
H70.8343411.9275911.0612190.080*
C200.892 (2)1.993 (2)1.1750 (2)0.042 (3)
C210.9025 (19)1.975 (2)1.1475 (2)0.039 (3)
C220.731 (2)2.022 (2)1.1311 (2)0.040 (3)
H220.6031822.0631481.1384870.048*
C230.748 (2)2.008 (2)1.1055 (3)0.044 (3)
H230.6325192.0440671.0950580.053*
C240.928 (2)1.9440 (17)1.0936 (3)0.042 (3)
C251.098 (2)1.892 (2)1.1097 (3)0.047 (3)
H251.2234341.8471781.1021420.057*
C261.083 (2)1.906 (2)1.1350 (3)0.045 (3)
H261.1984241.8681221.1452190.054*
O1W1.643 (3)1.102 (3)1.0427 (2)0.085 (5)
H1WA1.5646721.1870351.0500360.127*
H1WB1.5836491.0802691.0280150.127*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.031 (4)0.082 (8)0.062 (5)0.016 (5)0.011 (3)0.004 (4)
O10.013 (3)0.040 (5)0.054 (5)0.002 (4)0.003 (3)0.001 (3)
O20.013 (4)0.037 (5)0.056 (5)0.002 (4)0.002 (3)0.006 (3)
O30.012 (4)0.073 (8)0.054 (5)0.007 (5)0.003 (3)0.003 (4)
O40.076 (9)0.111 (14)0.051 (6)0.021 (10)0.014 (5)0.007 (6)
N10.024 (5)0.047 (7)0.062 (6)0.004 (5)0.003 (4)0.001 (5)
N20.007 (4)0.044 (6)0.053 (5)0.006 (5)0.003 (3)0.002 (4)
N30.023 (5)0.040 (6)0.044 (5)0.008 (5)0.004 (4)0.008 (4)
C10.014 (5)0.032 (6)0.063 (7)0.012 (5)0.000 (4)0.001 (5)
C20.015 (5)0.028 (6)0.054 (6)0.007 (4)0.003 (4)0.009 (4)
C30.021 (5)0.039 (7)0.041 (5)0.001 (5)0.004 (4)0.001 (4)
C40.014 (5)0.047 (8)0.049 (6)0.001 (6)0.002 (4)0.004 (5)
C50.003 (4)0.049 (7)0.054 (6)0.008 (5)0.004 (4)0.005 (5)
C60.009 (4)0.012 (4)0.074 (7)0.003 (4)0.010 (4)0.002 (4)
C70.006 (3)0.034 (5)0.062 (5)0.004 (3)0.005 (3)0.002 (3)
C80.006 (3)0.034 (5)0.062 (5)0.004 (3)0.005 (3)0.002 (3)
C90.013 (5)0.047 (8)0.064 (7)0.001 (6)0.012 (4)0.008 (6)
C100.011 (5)0.053 (9)0.059 (7)0.004 (6)0.005 (4)0.000 (5)
C110.022 (6)0.042 (8)0.058 (7)0.002 (6)0.003 (5)0.003 (5)
C120.022 (5)0.056 (9)0.051 (6)0.005 (6)0.003 (4)0.002 (5)
C130.067 (11)0.044 (9)0.061 (8)0.009 (9)0.005 (7)0.001 (6)
C140.075 (13)0.067 (12)0.067 (9)0.007 (11)0.002 (8)0.002 (8)
C150.059 (11)0.096 (18)0.064 (10)0.018 (12)0.005 (7)0.006 (9)
C160.036 (7)0.059 (11)0.070 (9)0.011 (8)0.001 (6)0.009 (7)
O50.031 (5)0.056 (7)0.056 (5)0.005 (5)0.005 (4)0.005 (4)
O60.031 (4)0.055 (6)0.043 (4)0.005 (4)0.000 (3)0.001 (3)
O70.051 (6)0.059 (7)0.049 (5)0.004 (6)0.002 (4)0.004 (4)
C200.027 (6)0.032 (7)0.067 (7)0.004 (6)0.007 (5)0.003 (5)
C210.020 (5)0.033 (7)0.063 (7)0.013 (6)0.001 (5)0.004 (5)
C220.033 (6)0.029 (6)0.059 (7)0.004 (6)0.003 (5)0.001 (5)
C230.030 (6)0.033 (7)0.069 (8)0.004 (6)0.006 (5)0.001 (5)
C240.025 (6)0.009 (5)0.093 (9)0.004 (5)0.001 (6)0.004 (5)
C250.031 (7)0.036 (8)0.075 (9)0.008 (7)0.008 (6)0.003 (6)
C260.028 (6)0.036 (8)0.070 (8)0.001 (6)0.004 (5)0.001 (6)
O1W0.096 (11)0.111 (13)0.047 (6)0.041 (10)0.000 (6)0.001 (6)
Geometric parameters (Å, º) top
F1—C91.378 (13)C10—C111.408 (17)
O1—C21.282 (14)C11—H110.9500
O2—C41.438 (12)C11—C121.365 (18)
O2—C61.317 (14)C12—H120.9500
O3—C61.218 (14)C13—H13A0.9900
O4—C141.48 (3)C13—H13B0.9900
O4—C151.39 (3)C13—C141.46 (2)
N1—C101.414 (18)C14—H14A0.9900
N1—C131.47 (2)C14—H14B0.9900
N1—C161.474 (19)C15—H15A0.9900
N2—C51.473 (13)C15—H15B0.9900
N2—C61.411 (13)C15—C161.49 (2)
N2—C71.360 (16)C16—H16A0.9900
N3—H30.8800C16—H16B0.9900
N3—C21.304 (16)O5—C201.228 (16)
N3—C31.463 (15)O6—H60.8400
C1—H1A0.9800O6—C201.303 (17)
C1—H1B0.9800O7—H70.8400
C1—H1C0.9800O7—C241.328 (17)
C1—C21.509 (15)C20—C211.437 (19)
C3—H3A0.9900C21—C221.433 (17)
C3—H3B0.9900C21—C261.414 (18)
C3—C41.504 (19)C22—H220.9500
C4—H41.0000C22—C231.341 (18)
C4—C51.537 (16)C23—H230.9500
C5—H5A0.9900C23—C241.388 (19)
C5—H5B0.9900C24—C251.42 (2)
C7—C81.428 (14)C25—H250.9500
C7—C121.423 (16)C25—C261.33 (2)
C8—H80.9500C26—H260.9500
C8—C91.327 (19)O1W—H1WA0.8693
C9—C101.427 (17)O1W—H1WB0.8673
C6—O2—C4110.4 (8)C12—C11—C10122.6 (12)
C15—O4—C14111.5 (14)C12—C11—H11118.7
C10—N1—C13114.1 (13)C7—C12—H12119.5
C10—N1—C16112.6 (11)C11—C12—C7121.1 (12)
C13—N1—C16107.9 (14)C11—C12—H12119.5
C6—N2—C5108.1 (9)N1—C13—H13A109.2
C7—N2—C5123.1 (9)N1—C13—H13B109.2
C7—N2—C6126.5 (9)H13A—C13—H13B107.9
C2—N3—H3118.8C14—C13—N1112.2 (16)
C2—N3—C3122.4 (9)C14—C13—H13A109.2
C3—N3—H3118.8C14—C13—H13B109.2
H1A—C1—H1B109.5O4—C14—H14A109.4
H1A—C1—H1C109.5O4—C14—H14B109.4
H1B—C1—H1C109.5C13—C14—O4111.2 (16)
C2—C1—H1A109.5C13—C14—H14A109.4
C2—C1—H1B109.5C13—C14—H14B109.4
C2—C1—H1C109.5H14A—C14—H14B108.0
O1—C2—N3120.9 (10)O4—C15—H15A108.7
O1—C2—C1121.0 (10)O4—C15—H15B108.7
N3—C2—C1118.1 (10)O4—C15—C16114 (2)
N3—C3—H3A109.1H15A—C15—H15B107.6
N3—C3—H3B109.1C16—C15—H15A108.7
N3—C3—C4112.4 (10)C16—C15—H15B108.7
H3A—C3—H3B107.9N1—C16—C15110.1 (14)
C4—C3—H3A109.1N1—C16—H16A109.6
C4—C3—H3B109.1N1—C16—H16B109.6
O2—C4—C3108.8 (11)C15—C16—H16A109.6
O2—C4—H4109.3C15—C16—H16B109.6
O2—C4—C5104.3 (8)H16A—C16—H16B108.2
C3—C4—H4109.3C20—O6—H6109.5
C3—C4—C5115.5 (11)C24—O7—H7109.5
C5—C4—H4109.3O5—C20—O6121.6 (12)
N2—C5—C4100.2 (9)O5—C20—C21122.5 (12)
N2—C5—H5A111.7O6—C20—C21115.9 (10)
N2—C5—H5B111.7C22—C21—C20122.5 (11)
C4—C5—H5A111.7C26—C21—C20121.6 (11)
C4—C5—H5B111.7C26—C21—C22115.9 (11)
H5A—C5—H5B109.5C21—C22—H22119.6
O2—C6—N2110.3 (9)C23—C22—C21120.8 (12)
O3—C6—O2123.1 (9)C23—C22—H22119.6
O3—C6—N2126.6 (10)C22—C23—H23118.9
N2—C7—C8122.7 (10)C22—C23—C24122.1 (12)
N2—C7—C12119.7 (9)C24—C23—H23118.9
C12—C7—C8117.6 (11)O7—C24—C23124.2 (12)
C7—C8—H8120.8O7—C24—C25118.1 (12)
C9—C8—C7118.4 (11)C23—C24—C25117.6 (13)
C9—C8—H8120.8C24—C25—H25119.7
F1—C9—C10115.2 (11)C26—C25—C24120.7 (14)
C8—C9—F1118.1 (11)C26—C25—H25119.7
C8—C9—C10126.7 (10)C21—C26—H26118.6
N1—C10—C9120.5 (10)C25—C26—C21122.7 (13)
C11—C10—N1125.9 (12)C25—C26—H26118.6
C11—C10—C9113.6 (11)H1WA—O1W—H1WB104.4
C10—C11—H11118.7
F1—C9—C10—N13 (2)C8—C7—C12—C113 (2)
F1—C9—C10—C11177.1 (13)C8—C9—C10—N1179.8 (15)
O2—C4—C5—N224.9 (13)C8—C9—C10—C110 (2)
O4—C15—C16—N157 (2)C9—C10—C11—C122 (2)
N1—C10—C11—C12178.4 (16)C10—N1—C13—C14175.5 (14)
N1—C13—C14—O456 (2)C10—N1—C16—C15176.3 (17)
N2—C7—C8—C9180.0 (13)C10—C11—C12—C73 (2)
N2—C7—C12—C11178.2 (14)C12—C7—C8—C91.0 (19)
N3—C3—C4—O2172.9 (9)C13—N1—C10—C965.7 (19)
N3—C3—C4—C570.3 (12)C13—N1—C10—C11114.2 (18)
C2—N3—C3—C484.9 (13)C13—N1—C16—C1556.8 (19)
C3—N3—C2—O19.4 (18)C14—O4—C15—C1653 (2)
C3—N3—C2—C1173.4 (12)C15—O4—C14—C1352 (2)
C3—C4—C5—N294.4 (12)C16—N1—C10—C9170.8 (15)
C4—O2—C6—O3172.6 (14)C16—N1—C10—C119 (2)
C4—O2—C6—N24.2 (15)C16—N1—C13—C1458.5 (19)
C5—N2—C6—O213.3 (15)O5—C20—C21—C22178.8 (14)
C5—N2—C6—O3170.0 (14)O5—C20—C21—C260 (2)
C5—N2—C7—C8179.2 (12)O6—C20—C21—C221 (2)
C5—N2—C7—C122 (2)O6—C20—C21—C26179.9 (14)
C6—O2—C4—C3104.8 (10)O7—C24—C25—C26179.9 (14)
C6—O2—C4—C519.1 (14)C20—C21—C22—C23178.2 (14)
C6—N2—C5—C423.3 (14)C20—C21—C26—C25178.5 (14)
C6—N2—C7—C820 (2)C21—C22—C23—C242 (2)
C6—N2—C7—C12158.8 (14)C22—C21—C26—C253 (2)
C7—N2—C5—C4173.0 (12)C22—C23—C24—O7179.7 (15)
C7—N2—C6—O2176.4 (12)C22—C23—C24—C250 (2)
C7—N2—C6—O37 (2)C23—C24—C25—C260 (2)
C7—C8—C9—F1176.7 (13)C24—C25—C26—C211 (2)
C7—C8—C9—C100 (2)C26—C21—C22—C233 (2)
(LIN:2,6-DHBA) top
Crystal data top
C16H20FN3O4·C7H6O4Dx = 1.456 Mg m3
Mr = 491.47Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121Cell parameters from 11050 reflections
a = 4.7535 (3) Åθ = 3.0–74.7°
b = 15.8010 (6) ŵ = 0.99 mm1
c = 29.8550 (11) ÅT = 293 K
V = 2242.42 (17) Å3Needle
Z = 40.47 × 0.09 × 0.05 mm
F(000) = 1032
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
4581 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source3744 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.087
Detector resolution: 4.1685 pixels mm-1θmax = 77.5°, θmin = 3.0°
ω scansh = 55
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1919
Tmin = 0.269, Tmax = 1.000l = 3737
29271 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.0746P)2]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.042(Δ/σ)max < 0.001
wR(F2) = 0.122Δρmax = 0.17 e Å3
S = 1.02Δρmin = 0.14 e Å3
4581 reflectionsExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
321 parametersExtinction coefficient: 0.0018 (5)
0 restraintsAbsolute structure: Flack x determined using 1310 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.13 (11)
Hydrogen site location: inferred from neighbouring sites
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F10.3959 (5)0.58263 (12)0.26302 (6)0.0762 (6)
O11.2809 (6)1.00463 (15)0.43806 (8)0.0752 (7)
O20.9674 (6)0.74121 (12)0.45850 (6)0.0683 (7)
O31.1623 (7)0.61554 (13)0.44513 (7)0.0772 (8)
O40.8180 (7)0.33357 (15)0.17837 (7)0.0772 (7)
N10.7230 (6)0.43711 (13)0.25544 (7)0.0550 (6)
N20.8263 (6)0.67239 (12)0.39801 (7)0.0519 (6)
N30.9601 (6)0.92428 (13)0.47189 (7)0.0566 (6)
H30.8788840.9099010.4964820.068*
C11.2057 (9)1.02874 (19)0.51626 (11)0.0704 (9)
H1A1.3939131.0168550.5260580.106*
H1B1.0743091.0087560.5382790.106*
H1C1.1831021.0886780.5124330.106*
C21.1520 (8)0.98486 (15)0.47252 (9)0.0555 (7)
C30.8834 (8)0.88146 (16)0.43060 (8)0.0592 (8)
H3A1.0495730.8752670.4120390.071*
H3B0.7491770.9160300.4143480.071*
C40.7580 (7)0.79615 (15)0.43879 (8)0.0534 (7)
H40.5946690.8009480.4586700.064*
C50.6746 (8)0.75191 (15)0.39522 (8)0.0559 (7)
H5A0.4731030.7426300.3937850.067*
H5B0.7331380.7844400.3692870.067*
C60.9958 (8)0.66986 (15)0.43393 (8)0.0570 (7)
C70.8057 (7)0.61067 (14)0.36350 (8)0.0514 (7)
C80.6162 (8)0.62442 (16)0.32886 (8)0.0556 (7)
H80.5041890.6726750.3289490.067*
C90.5935 (8)0.56715 (16)0.29452 (8)0.0555 (7)
C100.7559 (7)0.49425 (15)0.29141 (8)0.0519 (7)
C110.9406 (8)0.48146 (16)0.32701 (9)0.0602 (8)
H111.0527200.4332180.3268790.072*
C120.9651 (8)0.53725 (17)0.36256 (9)0.0586 (8)
H121.0887270.5254130.3858710.070*
C130.7605 (9)0.47355 (18)0.21052 (9)0.0646 (9)
H13A0.9573890.4868560.2056810.077*
H13B0.6531690.5255510.2080310.077*
C140.6626 (11)0.4114 (2)0.17579 (10)0.0780 (11)
H14A0.4640680.3998380.1801630.094*
H14B0.6859140.4359030.1462290.094*
C150.7910 (10)0.29863 (19)0.22206 (10)0.0722 (10)
H15A0.9025240.2473390.2239180.087*
H15B0.5959510.2834340.2272080.087*
C160.8850 (9)0.35918 (16)0.25810 (9)0.0614 (8)
H16A0.8588780.3334060.2872880.074*
H16B1.0834770.3716750.2544150.074*
O50.3549 (6)0.62421 (13)0.06430 (8)0.0715 (6)
H50.4681390.5850730.0648680.107*
O60.2920 (7)0.58413 (14)0.13501 (8)0.0812 (8)
O70.0483 (8)0.66707 (17)0.18534 (9)0.0884 (9)
H70.0344750.6238540.1777620.133*
O80.0905 (7)0.75505 (16)0.03169 (8)0.0776 (7)
H8A0.2106970.7178200.0314550.116*
C200.2356 (8)0.63204 (17)0.10411 (10)0.0613 (8)
C210.0287 (7)0.70131 (16)0.10766 (10)0.0573 (7)
C220.1116 (9)0.71315 (18)0.14875 (11)0.0666 (8)
C230.3177 (9)0.7751 (2)0.15314 (14)0.0770 (10)
H230.4134490.7817100.1800780.092*
C240.3780 (9)0.8261 (2)0.11741 (15)0.0810 (11)
H240.5167870.8672250.1204260.097*
C250.2401 (9)0.8186 (2)0.07727 (13)0.0745 (10)
H250.2835420.8546160.0536430.089*
C260.0356 (8)0.75690 (18)0.07211 (11)0.0622 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0872 (15)0.0792 (10)0.0623 (9)0.0194 (11)0.0285 (10)0.0174 (8)
O10.0851 (19)0.0728 (12)0.0676 (12)0.0237 (13)0.0157 (12)0.0054 (9)
O20.102 (2)0.0509 (9)0.0524 (9)0.0055 (11)0.0212 (11)0.0076 (7)
O30.110 (2)0.0604 (10)0.0616 (11)0.0151 (13)0.0346 (13)0.0049 (8)
O40.098 (2)0.0760 (12)0.0581 (11)0.0133 (14)0.0017 (12)0.0174 (9)
N10.0720 (19)0.0479 (9)0.0451 (10)0.0006 (11)0.0015 (10)0.0044 (7)
N20.0662 (17)0.0455 (9)0.0440 (9)0.0010 (11)0.0076 (10)0.0026 (7)
N30.0733 (19)0.0495 (10)0.0472 (10)0.0111 (11)0.0115 (11)0.0059 (8)
C10.081 (3)0.0609 (14)0.0689 (16)0.0030 (17)0.0031 (17)0.0169 (12)
C20.063 (2)0.0463 (11)0.0574 (13)0.0014 (12)0.0022 (13)0.0039 (9)
C30.082 (2)0.0513 (12)0.0442 (11)0.0077 (14)0.0052 (13)0.0038 (9)
C40.066 (2)0.0492 (11)0.0450 (11)0.0013 (12)0.0033 (12)0.0031 (9)
C50.071 (2)0.0474 (10)0.0497 (11)0.0034 (13)0.0045 (13)0.0039 (9)
C60.080 (2)0.0461 (11)0.0452 (11)0.0032 (13)0.0119 (13)0.0014 (8)
C70.062 (2)0.0470 (10)0.0449 (11)0.0014 (12)0.0032 (12)0.0022 (8)
C80.067 (2)0.0491 (11)0.0503 (12)0.0057 (13)0.0083 (12)0.0035 (9)
C90.063 (2)0.0563 (12)0.0467 (11)0.0039 (13)0.0114 (12)0.0030 (10)
C100.063 (2)0.0466 (10)0.0457 (11)0.0027 (12)0.0006 (11)0.0014 (9)
C110.076 (2)0.0486 (11)0.0562 (13)0.0078 (13)0.0074 (13)0.0027 (9)
C120.072 (2)0.0522 (12)0.0518 (12)0.0058 (14)0.0133 (13)0.0026 (9)
C130.086 (3)0.0599 (13)0.0483 (12)0.0032 (16)0.0035 (14)0.0007 (10)
C140.099 (3)0.086 (2)0.0485 (13)0.018 (2)0.0012 (16)0.0153 (13)
C150.092 (3)0.0578 (14)0.0666 (16)0.0030 (17)0.0035 (17)0.0153 (12)
C160.079 (2)0.0496 (12)0.0555 (13)0.0009 (14)0.0010 (14)0.0039 (10)
O50.0748 (18)0.0631 (11)0.0765 (13)0.0149 (12)0.0071 (12)0.0011 (9)
O60.099 (2)0.0643 (11)0.0805 (14)0.0138 (14)0.0016 (14)0.0126 (10)
O70.110 (3)0.0785 (14)0.0764 (13)0.0013 (16)0.0176 (15)0.0096 (11)
O80.0807 (19)0.0819 (14)0.0702 (12)0.0147 (14)0.0001 (12)0.0086 (10)
C200.066 (2)0.0501 (11)0.0680 (15)0.0026 (14)0.0017 (14)0.0011 (10)
C210.054 (2)0.0471 (12)0.0708 (15)0.0045 (12)0.0021 (14)0.0063 (10)
C220.070 (2)0.0565 (13)0.0729 (16)0.0092 (16)0.0022 (16)0.0063 (12)
C230.061 (2)0.0770 (18)0.093 (2)0.0066 (18)0.0116 (19)0.0241 (17)
C240.060 (2)0.0690 (17)0.114 (3)0.0095 (18)0.008 (2)0.0254 (18)
C250.066 (3)0.0620 (15)0.095 (2)0.0118 (17)0.0149 (19)0.0051 (15)
C260.060 (2)0.0556 (13)0.0712 (16)0.0007 (14)0.0074 (15)0.0050 (11)
Geometric parameters (Å, º) top
F1—C91.352 (4)C7—C121.386 (4)
O1—C21.238 (4)C8—C91.372 (3)
O2—C41.446 (4)C9—C101.390 (4)
O2—C61.352 (3)C10—C111.393 (4)
O3—C61.214 (4)C11—C121.385 (4)
O4—C141.437 (4)C13—C141.502 (4)
O4—C151.422 (4)C15—C161.508 (4)
N1—C101.412 (3)O5—C201.323 (4)
N1—C131.470 (3)O6—C201.223 (4)
N1—C161.455 (4)O7—C221.347 (4)
N2—C51.451 (3)O8—C261.348 (4)
N2—C61.342 (4)C20—C211.475 (4)
N2—C71.422 (3)C21—C221.409 (5)
N3—C21.322 (4)C21—C261.411 (4)
N3—C31.453 (3)C22—C231.391 (5)
C1—C21.500 (4)C23—C241.368 (6)
C3—C41.494 (4)C24—C251.371 (6)
C4—C51.529 (3)C25—C261.385 (5)
C7—C81.389 (4)
C6—O2—C4110.4 (2)C8—C9—C10123.6 (3)
C15—O4—C14109.6 (2)C9—C10—N1121.3 (2)
C10—N1—C13115.5 (2)C9—C10—C11114.8 (2)
C10—N1—C16116.2 (2)C11—C10—N1123.9 (2)
C16—N1—C13108.5 (2)C12—C11—C10123.0 (3)
C6—N2—C5111.7 (2)C11—C12—C7120.2 (3)
C6—N2—C7126.9 (2)N1—C13—C14109.6 (3)
C7—N2—C5121.2 (2)O4—C14—C13111.3 (3)
C2—N3—C3121.5 (2)O4—C15—C16112.4 (3)
O1—C2—N3120.8 (2)N1—C16—C15110.0 (3)
O1—C2—C1121.5 (3)O5—C20—C21114.8 (3)
N3—C2—C1117.7 (3)O6—C20—O5121.7 (3)
N3—C3—C4112.4 (2)O6—C20—C21123.5 (3)
O2—C4—C3109.5 (3)C22—C21—C20118.5 (3)
O2—C4—C5104.5 (2)C22—C21—C26118.0 (3)
C3—C4—C5112.1 (2)C26—C21—C20123.5 (3)
N2—C5—C4102.6 (2)O7—C22—C21121.9 (3)
O3—C6—O2120.3 (2)O7—C22—C23117.5 (3)
O3—C6—N2129.2 (2)C23—C22—C21120.6 (3)
N2—C6—O2110.4 (2)C24—C23—C22119.3 (3)
C8—C7—N2118.5 (2)C23—C24—C25122.0 (4)
C12—C7—N2123.5 (3)C24—C25—C26119.6 (3)
C12—C7—C8118.1 (2)O8—C26—C21124.3 (3)
C9—C8—C7120.3 (3)O8—C26—C25115.3 (3)
F1—C9—C8117.1 (3)C25—C26—C21120.4 (3)
F1—C9—C10119.3 (2)
(LIN:3,4-DHBA:H2O) top
Crystal data top
2(C16H20FN3O4)·2(C7H6O4)·1.25(H2O)Dx = 1.411 Mg m3
Mr = 1005.45Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P21212Cell parameters from 38569 reflections
a = 30.3989 (2) Åθ = 2.9–75.1°
b = 16.10240 (15) ŵ = 0.97 mm1
c = 9.66944 (7) ÅT = 293 K
V = 4733.14 (7) Å3Plate
Z = 40.33 × 0.15 × 0.09 mm
F(000) = 2114
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
9687 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source9333 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.027
Detector resolution: 4.1685 pixels mm-1θmax = 75.3°, θmin = 2.9°
ω scansh = 3838
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 2016
Tmin = 0.790, Tmax = 1.000l = 1212
61242 measured reflections
Refinement top
Refinement on F2H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.1003P)2 + 0.451P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.044(Δ/σ)max < 0.001
wR(F2) = 0.134Δρmax = 0.47 e Å3
S = 1.02Δρmin = 0.32 e Å3
9687 reflectionsExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
684 parametersExtinction coefficient: 0.00034 (10)
0 restraintsAbsolute structure: Flack x determined using 3979 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.05 (3)
Hydrogen site location: mixed
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.52546 (6)0.18385 (15)0.04172 (18)0.0711 (5)
O1A0.22670 (7)0.15918 (15)0.64836 (19)0.0599 (5)
O2A0.32240 (6)0.16722 (14)0.2566 (2)0.0567 (4)
O3A0.36986 (7)0.1716 (2)0.0805 (2)0.0761 (7)
O4A0.66581 (6)0.06542 (14)0.2581 (2)0.0613 (5)
N1A0.57873 (6)0.13089 (14)0.2523 (2)0.0494 (4)
N2A0.39343 (7)0.15531 (15)0.3071 (2)0.0488 (5)
N3A0.24620 (7)0.12997 (16)0.4287 (2)0.0506 (5)
H3A0.2381280.1294420.3435070.061*
C1A0.17052 (9)0.1636 (2)0.4761 (3)0.0615 (7)
H1AA0.1509090.1329850.5349410.092*
H1AB0.1677890.1438790.3828230.092*
H1AC0.1631480.2215170.4795510.092*
C2A0.21681 (8)0.15170 (16)0.5245 (3)0.0455 (5)
C3A0.29116 (8)0.10719 (19)0.4618 (3)0.0522 (6)
H3AA0.2971530.0524120.4245550.063*
H3AB0.2943430.1042340.5614710.063*
C4A0.32434 (8)0.16724 (17)0.4055 (3)0.0488 (5)
H4A0.3182780.2231510.4407020.059*
C5A0.37172 (8)0.1429 (2)0.4389 (3)0.0529 (6)
H5AA0.3841130.1784050.5098960.063*
H5AB0.3736480.0854430.4685400.063*
C6A0.36350 (9)0.1655 (2)0.2026 (3)0.0537 (6)
C7A0.43952 (8)0.14859 (16)0.2913 (3)0.0458 (5)
C8A0.46046 (8)0.16710 (19)0.1675 (3)0.0509 (6)
H8A0.4443560.1834540.0903660.061*
C9A0.50567 (8)0.16070 (18)0.1613 (3)0.0494 (5)
C10A0.53229 (8)0.13505 (16)0.2699 (3)0.0473 (5)
C11A0.51019 (8)0.1165 (2)0.3922 (3)0.0567 (6)
H11A0.5262920.0986680.4684720.068*
C12A0.46491 (8)0.1237 (2)0.4036 (3)0.0565 (7)
H12A0.4513140.1117940.4874880.068*
C13A0.59295 (9)0.0661 (2)0.1542 (3)0.0567 (6)
H13C0.5776350.0730810.0670260.068*
H13D0.5855890.0117300.1908500.068*
C14A0.64219 (9)0.0716 (2)0.1306 (3)0.0582 (6)
H14C0.6513530.0272750.0692050.070*
H14D0.6491130.1241060.0864220.070*
C15A0.65238 (9)0.1305 (3)0.3493 (4)0.0674 (8)
H15C0.6586280.1838580.3070620.081*
H15D0.6689700.1269020.4347780.081*
C16A0.60371 (9)0.1244 (2)0.3807 (3)0.0618 (7)
H16C0.5974240.0718040.4253760.074*
H16D0.5951910.1687390.4431950.074*
O5A0.90944 (6)0.28778 (12)0.2511 (2)0.0579 (4)
O6A0.94463 (6)0.16856 (14)0.2154 (3)0.0612 (5)
H6A0.9657190.1958420.2424220.16 (3)*
O7A0.74718 (6)0.19199 (13)0.2431 (3)0.0681 (6)
H7A0.7480670.2380650.2791650.102*
O8A0.75294 (6)0.02642 (12)0.2270 (3)0.0605 (5)
H8AA0.7316200.0560220.2433350.091*
C20A0.90922 (8)0.21048 (16)0.2325 (3)0.0456 (5)
C21A0.86761 (7)0.16369 (16)0.2311 (2)0.0439 (5)
C22A0.82697 (8)0.20518 (15)0.2388 (3)0.0473 (5)
H22A0.8260110.2628260.2439640.057*
C23A0.78837 (8)0.15939 (16)0.2385 (3)0.0481 (5)
C24A0.78979 (8)0.07272 (16)0.2289 (3)0.0471 (5)
C25A0.83038 (8)0.03211 (16)0.2222 (3)0.0501 (5)
H25A0.8314340.0255130.2167190.060*
C26A0.86883 (8)0.07738 (16)0.2239 (3)0.0475 (5)
H26A0.8957710.0501130.2201320.057*
F1B0.59101 (6)0.65823 (19)0.48400 (18)0.0827 (7)
O1B0.29761 (7)0.67170 (13)0.14862 (18)0.0544 (4)
O2B0.3926 (4)0.623 (2)0.2556 (15)0.086 (5)0.63 (5)
O3B0.4382 (3)0.640 (3)0.4306 (9)0.120 (8)0.63 (5)
C6B0.4305 (4)0.6268 (19)0.3018 (12)0.084 (5)0.63 (5)
O2B'0.3912 (6)0.5944 (10)0.235 (3)0.056 (4)0.37 (5)
O3B'0.4376 (5)0.5932 (15)0.4206 (19)0.072 (5)0.37 (5)
C6B'0.4353 (6)0.6008 (12)0.307 (2)0.053 (4)0.37 (5)
O4B0.73722 (6)0.57266 (13)0.2591 (3)0.0609 (5)
N1B0.64850 (6)0.62900 (14)0.2669 (2)0.0472 (4)
N2B0.46315 (7)0.61833 (18)0.2033 (2)0.0552 (6)
N3B0.31985 (7)0.65756 (17)0.0715 (2)0.0545 (5)
H3B0.3122070.6499030.1561800.065*
C1B0.24365 (9)0.6315 (2)0.0185 (3)0.0603 (7)
H1BA0.2235410.6757580.0019770.090*
H1BB0.2435680.6208570.1161830.090*
H1BC0.2347580.5822390.0300430.090*
C2B0.28891 (8)0.65565 (17)0.0262 (2)0.0461 (5)
C3B0.36590 (8)0.6721 (2)0.0405 (3)0.0571 (6)
H3BA0.3745920.7257260.0770090.068*
H3BB0.3699840.6732000.0589280.068*
C4B0.39428 (8)0.60655 (19)0.1012 (3)0.0532 (6)
H4B0.3833470.5508940.0788770.064*0.63 (5)
H4BA0.3848620.5544170.0581310.064*0.37 (5)
C5B0.44318 (8)0.6152 (2)0.0674 (3)0.0538 (6)
H5BA0.4537540.5678700.0149810.065*
H5BB0.4489580.6656380.0156800.065*
C7B0.50926 (8)0.62137 (18)0.2218 (3)0.0491 (5)
C8B0.52868 (9)0.6368 (2)0.3500 (3)0.0585 (7)
H8B0.5114230.6452450.4281060.070*
C9B0.57342 (9)0.6393 (2)0.3586 (3)0.0549 (7)
C10B0.60233 (7)0.62554 (15)0.2486 (3)0.0442 (5)
C11B0.58164 (8)0.61327 (19)0.1220 (3)0.0476 (5)
H11B0.5989490.6056310.0437600.057*
C12B0.53645 (8)0.61196 (19)0.1078 (3)0.0497 (5)
H12B0.5241070.6046680.0206130.060*
C13B0.66577 (9)0.5680 (2)0.3673 (3)0.0571 (6)
H13A0.6601390.5121960.3339230.069*
H13B0.6507650.5746750.4551150.069*
C14B0.71453 (9)0.5800 (2)0.3875 (3)0.0588 (7)
H14A0.7199730.6344050.4268480.071*
H14B0.7255270.5386040.4516700.071*
C15B0.72206 (8)0.6361 (2)0.1672 (3)0.0592 (7)
H15A0.7384490.6334180.0811840.071*
H15B0.7270390.6901810.2083550.071*
C16B0.67361 (8)0.6249 (2)0.1381 (3)0.0533 (6)
H16A0.6636300.6679800.0754300.064*
H16B0.6687640.5715420.0939280.064*
O5B0.97971 (6)0.75612 (11)0.2442 (3)0.0581 (5)
O6B1.01418 (6)0.63447 (12)0.2482 (3)0.0614 (5)
H6B1.0355630.6648850.2377690.107 (17)*
O7B0.81741 (6)0.67448 (12)0.2447 (3)0.0677 (6)
H7B0.8198380.7219740.2151070.101*
O8B0.81834 (6)0.50739 (12)0.2453 (3)0.0635 (5)
H8BA0.7976590.5400870.2461730.095*
C20B0.97904 (7)0.67803 (15)0.2465 (3)0.0463 (5)
C21B0.93658 (7)0.63363 (15)0.2462 (3)0.0448 (5)
C22B0.89715 (7)0.67839 (15)0.2457 (3)0.0453 (5)
H22B0.8977340.7361280.2464820.054*
C23B0.85731 (7)0.63702 (15)0.2442 (3)0.0456 (5)
C24B0.85639 (8)0.54984 (15)0.2449 (3)0.0476 (5)
C25B0.89551 (8)0.50601 (16)0.2444 (4)0.0564 (6)
H25B0.8949760.4482630.2437400.068*
C26B0.93557 (8)0.54741 (16)0.2448 (3)0.0539 (6)
H26B0.9617130.5174170.2442240.065*
O2W0.92434 (17)0.9013 (3)0.2829 (5)0.1366 (16)
H2WA0.9463790.9338360.2836040.205*
H2WB0.9360590.8540160.2697140.205*
O1W1.0000001.0000000.1976 (14)0.136 (4)0.5
H1WA1.0136800.9669000.2508620.205*0.25
H1WB0.9862201.0331000.2508620.205*0.25
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0550 (9)0.1109 (15)0.0474 (8)0.0095 (9)0.0108 (7)0.0230 (9)
O1A0.0632 (11)0.0760 (13)0.0406 (9)0.0014 (10)0.0018 (8)0.0084 (9)
O2A0.0380 (8)0.0830 (12)0.0492 (9)0.0015 (8)0.0051 (7)0.0045 (10)
O3A0.0509 (10)0.136 (2)0.0419 (10)0.0018 (13)0.0055 (8)0.0111 (12)
O4A0.0432 (9)0.0757 (12)0.0649 (12)0.0061 (8)0.0001 (9)0.0017 (11)
N1A0.0398 (9)0.0615 (11)0.0468 (10)0.0018 (8)0.0012 (8)0.0027 (10)
N2A0.0383 (10)0.0675 (13)0.0406 (10)0.0001 (9)0.0022 (8)0.0013 (9)
N3A0.0399 (10)0.0708 (14)0.0412 (10)0.0021 (9)0.0023 (8)0.0031 (9)
C1A0.0457 (13)0.087 (2)0.0517 (14)0.0056 (14)0.0046 (11)0.0022 (14)
C2A0.0463 (12)0.0493 (13)0.0409 (11)0.0027 (10)0.0049 (9)0.0013 (9)
C3A0.0409 (11)0.0620 (15)0.0538 (13)0.0013 (11)0.0019 (10)0.0020 (12)
C4A0.0412 (11)0.0582 (13)0.0469 (12)0.0015 (10)0.0015 (9)0.0027 (11)
C5A0.0375 (11)0.0788 (18)0.0424 (12)0.0005 (11)0.0004 (9)0.0003 (11)
C6A0.0422 (12)0.0746 (17)0.0441 (12)0.0005 (12)0.0055 (9)0.0026 (12)
C7A0.0392 (11)0.0556 (13)0.0426 (11)0.0004 (9)0.0021 (9)0.0004 (10)
C8A0.0446 (12)0.0648 (15)0.0434 (12)0.0028 (11)0.0025 (10)0.0058 (11)
C9A0.0465 (12)0.0608 (14)0.0409 (11)0.0012 (11)0.0054 (10)0.0061 (11)
C10A0.0399 (11)0.0575 (12)0.0446 (12)0.0015 (9)0.0004 (10)0.0000 (11)
C11A0.0419 (12)0.0859 (19)0.0424 (12)0.0006 (12)0.0025 (9)0.0065 (13)
C12A0.0407 (12)0.089 (2)0.0396 (11)0.0005 (12)0.0007 (10)0.0079 (13)
C13A0.0477 (13)0.0646 (16)0.0579 (15)0.0044 (12)0.0022 (11)0.0085 (13)
C14A0.0503 (13)0.0688 (17)0.0555 (14)0.0077 (12)0.0041 (11)0.0012 (13)
C15A0.0400 (13)0.099 (2)0.0631 (17)0.0002 (14)0.0001 (12)0.0105 (17)
C16A0.0417 (12)0.095 (2)0.0487 (13)0.0019 (13)0.0005 (10)0.0033 (14)
O5A0.0490 (9)0.0529 (9)0.0719 (12)0.0047 (7)0.0035 (9)0.0063 (10)
O6A0.0402 (8)0.0648 (11)0.0786 (14)0.0003 (8)0.0088 (9)0.0155 (10)
O7A0.0383 (8)0.0575 (10)0.1084 (18)0.0025 (7)0.0030 (11)0.0078 (13)
O8A0.0420 (8)0.0548 (10)0.0848 (14)0.0052 (7)0.0047 (9)0.0008 (10)
C20A0.0417 (11)0.0539 (12)0.0413 (10)0.0000 (9)0.0022 (9)0.0030 (10)
C21A0.0394 (10)0.0526 (12)0.0396 (10)0.0017 (9)0.0014 (9)0.0015 (10)
C22A0.0427 (11)0.0474 (11)0.0519 (12)0.0010 (9)0.0011 (10)0.0035 (11)
C23A0.0399 (10)0.0531 (12)0.0512 (12)0.0025 (9)0.0008 (10)0.0007 (11)
C24A0.0420 (11)0.0511 (12)0.0483 (12)0.0024 (9)0.0022 (10)0.0019 (10)
C25A0.0472 (12)0.0471 (12)0.0561 (14)0.0001 (10)0.0028 (10)0.0023 (10)
C26A0.0412 (11)0.0533 (12)0.0479 (12)0.0043 (9)0.0017 (10)0.0010 (10)
F1B0.0533 (9)0.154 (2)0.0411 (8)0.0033 (11)0.0074 (7)0.0201 (11)
O1B0.0602 (10)0.0617 (11)0.0412 (8)0.0030 (9)0.0015 (8)0.0040 (8)
O2B0.037 (2)0.177 (13)0.045 (3)0.002 (6)0.0042 (19)0.014 (7)
O3B0.047 (3)0.27 (3)0.048 (2)0.017 (7)0.0075 (18)0.010 (7)
C6B0.037 (3)0.167 (13)0.049 (3)0.034 (6)0.015 (2)0.044 (6)
O2B'0.025 (3)0.084 (7)0.058 (9)0.006 (3)0.002 (4)0.021 (5)
O3B'0.050 (4)0.124 (11)0.043 (5)0.001 (5)0.008 (3)0.030 (5)
C6B'0.025 (5)0.076 (9)0.059 (7)0.015 (5)0.006 (4)0.025 (5)
O4B0.0392 (8)0.0661 (11)0.0774 (13)0.0070 (8)0.0009 (9)0.0061 (11)
N1B0.0361 (9)0.0603 (11)0.0451 (10)0.0016 (8)0.0019 (8)0.0039 (9)
N2B0.0334 (10)0.0857 (16)0.0464 (11)0.0004 (10)0.0039 (8)0.0089 (11)
N3B0.0378 (10)0.0822 (16)0.0433 (10)0.0048 (10)0.0019 (8)0.0106 (10)
C1B0.0445 (13)0.087 (2)0.0499 (14)0.0023 (13)0.0022 (10)0.0003 (14)
C2B0.0436 (11)0.0530 (13)0.0417 (11)0.0066 (10)0.0000 (9)0.0006 (10)
C3B0.0408 (12)0.0687 (17)0.0616 (15)0.0027 (12)0.0026 (11)0.0164 (13)
C4B0.0362 (11)0.0610 (15)0.0624 (15)0.0024 (10)0.0001 (10)0.0103 (12)
C5B0.0351 (11)0.0763 (17)0.0501 (13)0.0016 (12)0.0003 (9)0.0060 (13)
C7B0.0367 (11)0.0667 (15)0.0440 (12)0.0026 (10)0.0026 (9)0.0044 (11)
C8B0.0432 (12)0.091 (2)0.0416 (12)0.0030 (13)0.0031 (10)0.0000 (13)
C9B0.0454 (12)0.0836 (19)0.0357 (11)0.0033 (12)0.0024 (10)0.0046 (11)
C10B0.0363 (10)0.0552 (12)0.0411 (11)0.0006 (9)0.0008 (9)0.0006 (10)
C11B0.0384 (11)0.0656 (15)0.0388 (11)0.0017 (10)0.0027 (9)0.0005 (10)
C12B0.0373 (11)0.0708 (15)0.0409 (11)0.0017 (11)0.0012 (9)0.0019 (11)
C13B0.0433 (12)0.0690 (16)0.0591 (15)0.0016 (12)0.0062 (11)0.0140 (13)
C14B0.0444 (13)0.0709 (17)0.0611 (16)0.0032 (12)0.0101 (11)0.0065 (13)
C15B0.0363 (11)0.0768 (18)0.0646 (16)0.0008 (11)0.0008 (11)0.0107 (14)
C16B0.0374 (11)0.0746 (17)0.0479 (13)0.0011 (11)0.0007 (10)0.0022 (12)
O5B0.0430 (8)0.0501 (9)0.0811 (13)0.0010 (7)0.0015 (10)0.0046 (10)
O6B0.0365 (8)0.0593 (10)0.0883 (14)0.0030 (8)0.0047 (10)0.0112 (11)
O7B0.0382 (8)0.0488 (9)0.1160 (18)0.0034 (7)0.0034 (11)0.0071 (12)
O8B0.0398 (8)0.0493 (9)0.1013 (16)0.0030 (7)0.0029 (10)0.0041 (11)
C20B0.0390 (10)0.0516 (12)0.0483 (12)0.0020 (9)0.0021 (10)0.0035 (11)
C21B0.0405 (11)0.0491 (11)0.0448 (11)0.0010 (9)0.0006 (9)0.0045 (10)
C22B0.0403 (10)0.0442 (11)0.0514 (12)0.0011 (9)0.0024 (10)0.0024 (10)
C23B0.0372 (10)0.0475 (11)0.0522 (12)0.0036 (8)0.0020 (10)0.0029 (10)
C24B0.0395 (10)0.0472 (12)0.0560 (13)0.0009 (9)0.0018 (10)0.0043 (11)
C25B0.0443 (12)0.0453 (11)0.0797 (18)0.0025 (9)0.0015 (13)0.0065 (13)
C26B0.0392 (11)0.0497 (12)0.0728 (16)0.0063 (9)0.0027 (12)0.0047 (13)
O2W0.185 (4)0.116 (3)0.109 (3)0.057 (3)0.006 (3)0.010 (2)
O1W0.137 (10)0.149 (10)0.123 (9)0.021 (8)0.0000.000
Geometric parameters (Å, º) top
F1A—C9A1.356 (3)O2B—C6B1.24 (2)
O1A—C2A1.240 (3)O2B—C4B1.517 (17)
O2A—C4A1.441 (3)O3B—C6B1.285 (17)
O2A—C6A1.354 (3)C6B—N2B1.381 (12)
O3A—C6A1.200 (4)O2B'—C6B'1.51 (3)
O4A—C14A1.429 (4)O2B'—C4B1.31 (3)
O4A—C15A1.430 (4)O3B'—C6B'1.11 (3)
N1A—C10A1.423 (3)C6B'—N2B1.34 (2)
N1A—C13A1.475 (4)O4B—C14B1.425 (4)
N1A—C16A1.459 (4)O4B—C15B1.430 (4)
N2A—C5A1.449 (3)N1B—C10B1.416 (3)
N2A—C6A1.369 (3)N1B—C13B1.477 (3)
N2A—C7A1.414 (3)N1B—C16B1.462 (3)
N3A—C2A1.334 (3)N2B—C5B1.449 (3)
N3A—C3A1.451 (3)N2B—C7B1.414 (3)
C1A—C2A1.495 (4)N3B—C2B1.333 (3)
C3A—C4A1.500 (4)N3B—C3B1.450 (3)
C4A—C5A1.527 (3)C1B—C2B1.494 (4)
C7A—C8A1.388 (4)C3B—C4B1.484 (4)
C7A—C12A1.392 (3)C4B—C5B1.528 (3)
C8A—C9A1.379 (3)C7B—C8B1.395 (4)
C9A—C10A1.388 (4)C7B—C12B1.387 (3)
C10A—C11A1.393 (4)C8B—C9B1.363 (4)
C11A—C12A1.386 (3)C9B—C10B1.398 (3)
C13A—C14A1.517 (4)C10B—C11B1.390 (3)
C15A—C16A1.513 (4)C11B—C12B1.381 (3)
O5A—C20A1.258 (3)C13B—C14B1.507 (4)
O6A—C20A1.281 (3)C15B—C16B1.510 (3)
O7A—C23A1.358 (3)O5B—C20B1.258 (3)
O8A—C24A1.346 (3)O6B—C20B1.278 (3)
C20A—C21A1.472 (3)O7B—C23B1.355 (3)
C21A—C22A1.407 (3)O8B—C24B1.344 (3)
C21A—C26A1.392 (4)C20B—C21B1.476 (3)
C22A—C23A1.386 (3)C21B—C22B1.399 (3)
C23A—C24A1.399 (4)C21B—C26B1.389 (4)
C24A—C25A1.398 (3)C22B—C23B1.382 (3)
C25A—C26A1.377 (4)C23B—C24B1.404 (4)
F1B—C9B1.360 (3)C24B—C25B1.383 (3)
O1B—C2B1.240 (3)C25B—C26B1.388 (4)
C6A—O2A—C4A110.32 (19)C4B—O2B'—C6B'112.3 (15)
C14A—O4A—C15A109.7 (2)O3B'—C6B'—O2B'120.2 (18)
C10A—N1A—C13A113.6 (2)O3B'—C6B'—N2B136.3 (18)
C10A—N1A—C16A114.7 (2)N2B—C6B'—O2B'103.4 (18)
C16A—N1A—C13A110.1 (2)C14B—O4B—C15B109.1 (2)
C6A—N2A—C5A111.3 (2)C10B—N1B—C13B114.1 (2)
C6A—N2A—C7A126.0 (2)C10B—N1B—C16B114.2 (2)
C7A—N2A—C5A122.4 (2)C16B—N1B—C13B110.1 (2)
C2A—N3A—C3A123.0 (2)C6B—N2B—C5B109.1 (6)
O1A—C2A—N3A122.3 (2)C6B—N2B—C7B128.4 (6)
O1A—C2A—C1A121.2 (2)C6B'—N2B—C5B113.8 (9)
N3A—C2A—C1A116.5 (2)C6B'—N2B—C7B122.7 (9)
N3A—C3A—C4A113.0 (2)C7B—N2B—C5B122.1 (2)
O2A—C4A—C3A109.6 (2)C2B—N3B—C3B122.6 (2)
O2A—C4A—C5A104.5 (2)O1B—C2B—N3B121.4 (2)
C3A—C4A—C5A113.1 (2)O1B—C2B—C1B121.8 (2)
N2A—C5A—C4A102.0 (2)N3B—C2B—C1B116.8 (2)
O2A—C6A—N2A109.3 (2)N3B—C3B—C4B111.4 (2)
O3A—C6A—O2A121.7 (2)O2B—C4B—C5B103.2 (6)
O3A—C6A—N2A128.9 (3)O2B'—C4B—C3B117.1 (9)
C8A—C7A—N2A122.1 (2)O2B'—C4B—C5B107.1 (8)
C8A—C7A—C12A118.7 (2)C3B—C4B—O2B104.1 (10)
C12A—C7A—N2A119.2 (2)C3B—C4B—C5B114.6 (2)
C9A—C8A—C7A118.6 (2)N2B—C5B—C4B102.5 (2)
F1A—C9A—C8A117.3 (2)C8B—C7B—N2B122.6 (2)
F1A—C9A—C10A117.9 (2)C12B—C7B—N2B119.1 (2)
C8A—C9A—C10A124.8 (2)C12B—C7B—C8B118.3 (2)
C9A—C10A—N1A120.1 (2)C9B—C8B—C7B118.8 (2)
C9A—C10A—C11A115.1 (2)F1B—C9B—C8B117.0 (2)
C11A—C10A—N1A124.7 (2)F1B—C9B—C10B117.8 (2)
C12A—C11A—C10A121.9 (2)C8B—C9B—C10B125.2 (2)
C11A—C12A—C7A120.9 (2)C9B—C10B—N1B121.5 (2)
N1A—C13A—C14A110.1 (2)C11B—C10B—N1B124.4 (2)
O4A—C14A—C13A111.2 (2)C11B—C10B—C9B114.1 (2)
O4A—C15A—C16A110.8 (3)C12B—C11B—C10B122.7 (2)
N1A—C16A—C15A109.5 (2)C11B—C12B—C7B120.8 (2)
O5A—C20A—O6A122.4 (2)N1B—C13B—C14B110.5 (2)
O5A—C20A—C21A120.8 (2)O4B—C14B—C13B110.7 (2)
O6A—C20A—C21A116.8 (2)O4B—C15B—C16B110.2 (2)
C22A—C21A—C20A120.7 (2)N1B—C16B—C15B110.2 (2)
C26A—C21A—C20A119.2 (2)O5B—C20B—O6B122.4 (2)
C26A—C21A—C22A120.0 (2)O5B—C20B—C21B119.9 (2)
C23A—C22A—C21A119.4 (2)O6B—C20B—C21B117.7 (2)
O7A—C23A—C22A125.1 (2)C22B—C21B—C20B120.0 (2)
O7A—C23A—C24A114.6 (2)C26B—C21B—C20B120.2 (2)
C22A—C23A—C24A120.3 (2)C26B—C21B—C22B119.7 (2)
O8A—C24A—C23A121.8 (2)C23B—C22B—C21B120.2 (2)
O8A—C24A—C25A118.4 (2)O7B—C23B—C22B124.7 (2)
C25A—C24A—C23A119.8 (2)O7B—C23B—C24B115.3 (2)
C26A—C25A—C24A120.1 (2)C22B—C23B—C24B119.9 (2)
C25A—C26A—C21A120.4 (2)O8B—C24B—C23B121.7 (2)
C6B—O2B—C4B109.3 (10)O8B—C24B—C25B118.7 (2)
O2B—C6B—O3B121.8 (11)C25B—C24B—C23B119.6 (2)
O2B—C6B—N2B114.6 (11)C24B—C25B—C26B120.6 (2)
O3B—C6B—N2B123.6 (11)C25B—C26B—C21B120.0 (2)
(LIN:GA:H2O) top
Crystal data top
C16H20FN3O4·C7H6O5·H2OF(000) = 2208
Mr = 525.48Dx = 1.425 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54184 Å
a = 16.78184 (17) ÅCell parameters from 47167 reflections
b = 15.4762 (2) Åθ = 2.6–75.3°
c = 19.59820 (18) ŵ = 1.00 mm1
β = 105.7581 (10)°T = 293 K
V = 4898.74 (9) Å3Plate
Z = 80.43 × 0.18 × 0.07 mm
Data collection top
SuperNova, Dual, Cu at zero, TitanS2
diffractometer
19039 independent reflections
Radiation source: sealed X-ray tube, SuperNova (Cu) X-ray Source18059 reflections with I > 2σ(I)
Mirror monochromatorRint = 0.042
Detector resolution: 4.1685 pixels mm-1θmax = 75.6°, θmin = 2.3°
ω scansh = 2021
Absorption correction: multi-scan
CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
k = 1918
Tmin = 0.651, Tmax = 1.000l = 2424
79440 measured reflections
Refinement top
Refinement on F2H-atom parameters constrained
Least-squares matrix: full w = 1/[σ2(Fo2) + (0.079P)2 + 0.3717P]
where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.043(Δ/σ)max = 0.001
wR(F2) = 0.123Δρmax = 0.26 e Å3
S = 1.04Δρmin = 0.21 e Å3
19039 reflectionsExtinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1366 parametersExtinction coefficient: 0.00065 (8)
1 restraintAbsolute structure: Flack x determined using 7590 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.01 (5)
Hydrogen site location: mixed
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
F1A0.85466 (9)0.33695 (17)0.90939 (8)0.0653 (5)
O1A0.57304 (11)0.32992 (19)1.35952 (10)0.0598 (6)
O2A0.76777 (11)0.34092 (17)1.21054 (9)0.0553 (5)
O3A0.85403 (11)0.37670 (19)1.14612 (10)0.0607 (6)
O4A0.67657 (12)0.31366 (17)0.65540 (10)0.0581 (5)
N1A0.71023 (13)0.34905 (16)0.80259 (11)0.0442 (5)
N2A0.71886 (12)0.33428 (18)1.09350 (10)0.0466 (5)
N3A0.68591 (13)0.34206 (19)1.31926 (11)0.0482 (5)
H3A0.7391150.3405741.3304630.058*
C1A0.70453 (17)0.3353 (3)1.44559 (14)0.0589 (8)
H1AA0.6845350.3765741.4735780.088*
H1AB0.7598100.3504211.4450000.088*
H1AC0.7046580.2787471.4657780.088*
C2A0.64906 (15)0.3355 (2)1.37110 (13)0.0456 (6)
C3A0.64178 (15)0.3516 (2)1.24472 (12)0.0484 (6)
H3AA0.6374940.4124601.2323070.058*
H3AB0.5861630.3287681.2365230.058*
C4A0.68596 (14)0.3047 (2)1.19857 (12)0.0472 (6)
H4A0.6901710.2431501.2108850.057*
C5A0.64687 (15)0.3151 (2)1.11871 (13)0.0526 (7)
H5AA0.6197800.2623101.0977540.063*
H5AB0.6072310.3621591.1087060.063*
C6A0.78639 (15)0.3525 (2)1.14818 (13)0.0473 (6)
C7A0.71596 (15)0.3393 (2)1.02061 (12)0.0438 (5)
C8A0.78778 (15)0.3352 (2)0.99863 (13)0.0453 (5)
H8A0.8390150.3295731.0317510.054*
C9A0.78264 (15)0.3393 (2)0.92782 (14)0.0453 (5)
C10A0.70849 (15)0.34520 (19)0.87430 (13)0.0429 (5)
C11A0.63737 (16)0.3494 (2)0.89773 (14)0.0530 (7)
H11A0.5861580.3542960.8644740.064*
C12A0.64056 (16)0.3464 (2)0.96947 (14)0.0546 (7)
H12A0.5917720.3491550.9832390.065*
C13A0.73951 (17)0.2695 (2)0.77638 (14)0.0507 (6)
H13A0.6994820.2236250.7741560.061*
H13B0.7915550.2517110.8088080.061*
C14A0.75136 (17)0.2843 (3)0.70358 (14)0.0563 (7)
H14A0.7945840.3268910.7066120.068*
H14B0.7687340.2308340.6861070.068*
C15A0.6508 (2)0.3928 (2)0.68073 (15)0.0578 (7)
H15A0.6007580.4134870.6470840.069*
H15B0.6934790.4362260.6846890.069*
C16A0.63454 (17)0.3798 (2)0.75217 (13)0.0507 (6)
H16A0.6172310.4338880.7686760.061*
H16B0.5905370.3378780.7481880.061*
F1B0.60783 (12)0.5816 (2)0.87273 (10)0.0898 (9)
O1B0.34277 (11)0.54703 (17)1.32311 (11)0.0551 (5)
O2B0.53869 (11)0.54409 (18)1.17963 (9)0.0592 (6)
O3B0.62658 (12)0.5470 (2)1.11255 (11)0.0782 (9)
O4B0.43222 (13)0.56037 (17)0.62245 (10)0.0603 (6)
N1B0.46632 (15)0.53988 (18)0.77081 (11)0.0504 (5)
N2B0.48479 (13)0.54446 (19)1.06323 (11)0.0514 (6)
N3B0.46049 (13)0.56864 (19)1.29142 (12)0.0534 (6)
H3B0.5136900.5691241.3055690.064*
C1B0.47070 (16)0.5295 (3)1.41248 (15)0.0566 (7)
H1BA0.4840110.5823891.4386860.085*
H1BB0.5208710.5009641.4106340.085*
H1BC0.4399080.4925901.4354280.085*
C2B0.41973 (14)0.54901 (19)1.33872 (13)0.0451 (5)
C3B0.42189 (15)0.5893 (2)1.21766 (13)0.0525 (6)
H3BA0.4347690.6485821.2085160.063*
H3BB0.3622610.5844221.2082220.063*
C4B0.45109 (16)0.5305 (2)1.16924 (13)0.0505 (6)
H4B0.4410240.4703451.1800680.061*
C5B0.41277 (16)0.5479 (3)1.09039 (14)0.0570 (7)
H5BA0.3726480.5038571.0689820.068*
H5BB0.3864360.6042101.0826230.068*
C6B0.55648 (16)0.5457 (2)1.11681 (14)0.0543 (7)
C7B0.47945 (15)0.5459 (2)0.98982 (13)0.0484 (6)
C8B0.54722 (17)0.5669 (3)0.96537 (15)0.0574 (7)
H8B0.5972860.5823620.9970070.069*
C9B0.53940 (17)0.5644 (2)0.89411 (15)0.0554 (7)
C10B0.46645 (17)0.5442 (2)0.84273 (14)0.0489 (6)
C11B0.39932 (19)0.5253 (3)0.86878 (16)0.0639 (9)
H11B0.3486620.5122050.8369530.077*
C12B0.40546 (18)0.5253 (3)0.94078 (15)0.0643 (9)
H12B0.3593970.5113980.9563170.077*
C13B0.4794 (2)0.6228 (2)0.73937 (15)0.0554 (7)
H13C0.5251850.6533080.7711660.066*
H13D0.4301850.6583230.7320940.066*
C14B0.49818 (19)0.6070 (3)0.66951 (14)0.0586 (7)
H14C0.5058680.6618360.6481960.070*
H14D0.5491750.5742660.6773540.070*
C15B0.4166 (2)0.4807 (3)0.65312 (16)0.0644 (8)
H15C0.4649030.4437230.6603820.077*
H15D0.3705090.4515220.6205820.077*
C16B0.3968 (2)0.4945 (2)0.72348 (15)0.0586 (7)
H16C0.3466070.5283890.7164640.070*
H16D0.3883260.4392870.7438980.070*
F1C0.11287 (11)0.3385 (2)0.62387 (10)0.0934 (9)
O1C0.15341 (11)0.38778 (17)0.17495 (10)0.0533 (5)
O2C0.04082 (11)0.33573 (18)0.31718 (9)0.0576 (5)
O3C0.12912 (11)0.35481 (19)0.38285 (11)0.0629 (6)
O4C0.06624 (13)0.36872 (16)0.87343 (10)0.0580 (5)
N1C0.02964 (14)0.38386 (17)0.72409 (11)0.0483 (5)
N2C0.01228 (12)0.34506 (19)0.43328 (11)0.0501 (5)
N3C0.03619 (14)0.3846 (2)0.20955 (12)0.0578 (6)
H3C0.0167480.3788040.1962260.069*
C1C0.02484 (16)0.3895 (3)0.08468 (14)0.0555 (7)
H1CA0.0468210.4322340.0592320.083*
H1CB0.0311610.4042040.0832690.083*
H1CC0.0258560.3339600.0631570.083*
C2C0.07642 (14)0.38667 (19)0.16027 (13)0.0440 (5)
C3C0.07638 (18)0.3917 (3)0.28519 (14)0.0633 (8)
H3CA0.0659230.4487060.3013950.076*
H3CB0.1357220.3855580.2930730.076*
C4C0.04696 (15)0.3255 (2)0.32765 (13)0.0516 (6)
H4C0.0587740.2675400.3128010.062*
C5C0.08495 (16)0.3361 (3)0.40775 (14)0.0614 (8)
H5CA0.1171440.2856880.4280280.074*
H5CB0.1198000.3870100.4183370.074*
C6C0.05850 (15)0.3458 (2)0.37955 (13)0.0474 (6)
C7C0.01727 (15)0.3549 (2)0.50625 (14)0.0479 (6)
C8C0.05089 (16)0.3392 (3)0.53171 (14)0.0565 (7)
H8C0.1008350.3215980.5010180.068*
C9C0.04390 (17)0.3499 (3)0.60240 (15)0.0557 (7)
C1OC0.02899 (17)0.3734 (2)0.65227 (13)0.0472 (6)
C11C0.09652 (18)0.3878 (3)0.62541 (15)0.0598 (8)
H11C0.1469150.4037780.6563280.072*
C12C0.09079 (17)0.3790 (3)0.55376 (15)0.0609 (8)
H12C0.1370830.3895260.5375510.073*
C13C0.01166 (19)0.3047 (2)0.75796 (14)0.0534 (6)
H13E0.0579190.2650580.7647400.064*
H13F0.0369290.2768900.7275920.064*
C14C0.00335 (18)0.3254 (2)0.82867 (14)0.0546 (7)
H14E0.0520230.3617690.8214930.066*
H14F0.0135790.2723880.8512780.066*
C15C0.0852 (2)0.4455 (2)0.84039 (16)0.0621 (8)
H15E0.1334600.4730100.8714920.075*
H15F0.0391340.4854950.8331160.075*
C16D0.1019 (2)0.4261 (2)0.77005 (15)0.0570 (7)
H16E0.1132930.4793080.7482950.068*
H16F0.1498330.3887190.7771370.068*
F1D0.35577 (10)0.59351 (18)0.58997 (9)0.0713 (6)
O1D0.07886 (12)0.6060 (2)0.14188 (10)0.0657 (7)
O2D0.26878 (11)0.55280 (16)0.28991 (9)0.0539 (5)
O3D0.36038 (11)0.55366 (18)0.35378 (10)0.0597 (6)
O4D0.17975 (13)0.61932 (16)0.84391 (10)0.0574 (5)
N1D0.21292 (13)0.57918 (17)0.69762 (11)0.0454 (5)
N2D0.21944 (12)0.56266 (17)0.40668 (11)0.0459 (5)
N3D0.19271 (13)0.5891 (2)0.17980 (12)0.0517 (6)
H3D0.2442360.5751070.1679190.062*
C1D0.20443 (18)0.5706 (3)0.05537 (14)0.0580 (7)
H1DA0.2238560.6237530.0313030.087*
H1DB0.2509160.5355100.0573430.087*
H1DC0.1713510.5402470.0301830.087*
C2D0.15313 (16)0.5899 (2)0.12925 (14)0.0474 (6)
C3D0.15429 (16)0.6105 (2)0.25373 (13)0.0513 (6)
H3DA0.1701670.6685930.2632050.062*
H3DB0.0945570.6092310.2626050.062*
C4D0.17960 (15)0.5484 (2)0.30280 (12)0.0472 (6)
H4D0.1632550.4895930.2938390.057*
C5D0.14561 (16)0.5700 (2)0.38161 (14)0.0531 (7)
H5DA0.1033590.5291270.4053650.064*
H5DB0.1229210.6280360.3883610.064*
C6D0.28911 (15)0.5564 (2)0.35157 (13)0.0452 (6)
C7D0.21725 (15)0.56874 (19)0.47952 (13)0.0429 (5)
C8D0.28923 (15)0.5805 (2)0.50089 (13)0.0474 (6)
H8D0.3402100.5860060.4674080.057*
C9D0.28394 (15)0.5837 (2)0.57175 (14)0.0472 (6)
C10D0.21024 (16)0.57771 (18)0.62589 (13)0.0433 (5)
C11D0.13979 (16)0.5666 (2)0.60292 (14)0.0537 (7)
H11D0.0887740.5621190.6365120.064*
C12D0.14261 (15)0.5618 (2)0.53159 (14)0.0529 (7)
H12D0.0938530.5537640.5184860.064*
C13D0.23736 (18)0.6623 (2)0.72141 (14)0.0524 (6)
H13G0.2876370.6826970.6879530.063*
H13H0.1941580.7047150.7236000.063*
C14D0.25179 (18)0.6520 (3)0.79412 (15)0.0595 (8)
H14G0.2663490.7075180.8103250.071*
H14H0.2976920.6127240.7909740.071*
C15D0.1574 (2)0.5374 (2)0.82034 (15)0.0569 (7)
H15G0.2023230.4967060.8166740.068*
H15H0.1088580.5151960.8548470.068*
C10.13939 (17)0.5457 (2)0.74908 (13)0.0501 (6)
H1A0.0931240.5846640.7527850.060*
H1B0.1247940.4897150.7337870.060*
O5A0.30459 (12)0.26268 (19)0.67903 (10)0.0618 (6)
H5A0.3026380.2630030.7203820.093*
O6A0.43937 (12)0.24833 (17)0.73113 (10)0.0565 (5)
O7A0.28178 (12)0.3144 (2)0.42462 (10)0.0648 (7)
H7A0.2993670.3313790.3918200.097*
O8A0.44016 (11)0.30791 (17)0.41204 (9)0.0542 (5)
H8AA0.4897220.3039000.4150590.081*
O9A0.56896 (11)0.2723 (2)0.52600 (10)0.0624 (6)
H9A0.6039940.2731840.5644220.094*
C20A0.38139 (16)0.25756 (19)0.67720 (13)0.0451 (5)
C21A0.39562 (15)0.26645 (18)0.60661 (12)0.0422 (5)
C22A0.33044 (15)0.2846 (2)0.54709 (13)0.0459 (6)
H22A0.2764970.2879650.5509390.055*
C23A0.34657 (15)0.2976 (2)0.48210 (13)0.0460 (6)
C24A0.42745 (15)0.29359 (19)0.47674 (12)0.0428 (5)
C25A0.49230 (15)0.2750 (2)0.53648 (12)0.0444 (5)
C26A0.47628 (15)0.26100 (19)0.60113 (12)0.0439 (5)
H26A0.5193980.2479630.6408760.053*
O5B0.42822 (13)0.2554 (2)0.86314 (11)0.0656 (6)
H5B0.4304040.2488200.8221740.098*
O6B0.29499 (13)0.2752 (2)0.80878 (10)0.0698 (7)
O7B0.16646 (12)0.3507 (2)1.00616 (10)0.0681 (7)
H7B0.1316250.3474890.9677260.102*
O8B0.29231 (11)0.35176 (17)1.12392 (9)0.0556 (5)
H8BA0.2423660.3553391.1192730.083*
O9B0.45012 (12)0.3073 (2)1.11953 (10)0.0695 (7)
H9B0.4323670.3160811.1539800.104*
C20B0.35244 (17)0.2725 (2)0.86342 (13)0.0497 (6)
C21B0.33801 (16)0.2895 (2)0.93318 (13)0.0463 (6)
C22B0.25779 (16)0.3089 (2)0.93482 (13)0.0520 (7)
H22B0.2148900.3079930.8931990.062*
C23B0.24187 (15)0.3294 (2)0.99814 (13)0.0481 (6)
C24B0.30578 (15)0.3297 (2)1.06082 (12)0.0452 (6)
C25B0.38631 (15)0.3081 (2)1.05959 (13)0.0487 (6)
C26B0.40212 (15)0.2881 (2)0.99554 (13)0.0504 (6)
H26B0.4555120.2737380.9942590.060*
O5C0.05396 (13)0.66381 (17)0.76876 (10)0.0585 (5)
O6C0.18882 (12)0.6458 (2)0.81926 (11)0.0623 (6)
H6C0.1891650.6411090.7776630.094*
O7C0.07304 (12)0.6564 (2)0.97511 (10)0.0619 (6)
H7C0.1082800.6532750.9368970.093*
O8C0.05512 (11)0.61896 (17)1.08888 (9)0.0554 (5)
H8CA0.0053250.6206921.0853700.083*
O9C0.21367 (12)0.6092 (2)1.07597 (11)0.0682 (7)
H9C0.1970160.6070371.1115890.102*
C20C0.11344 (17)0.65600 (19)0.82270 (13)0.0460 (5)
C21C0.10003 (16)0.65312 (18)0.89390 (13)0.0431 (5)
C22C0.01945 (16)0.66215 (19)0.89938 (13)0.0454 (5)
H22C0.0234010.6759700.8596590.054*
C23C0.00378 (16)0.65038 (19)0.96446 (13)0.0447 (5)
C24C0.06792 (15)0.63171 (19)1.02425 (12)0.0430 (5)
C25C0.14915 (16)0.6251 (2)1.01863 (13)0.0469 (6)
C26C0.16473 (16)0.6355 (2)0.95329 (14)0.0476 (6)
H26C0.2184910.6306530.9492420.057*
O5D0.20197 (13)0.6304 (2)0.69097 (10)0.0699 (7)
O6D0.06747 (12)0.64466 (19)0.63859 (11)0.0623 (6)
H6D0.0664600.6500970.6799630.093*
O7D0.33074 (12)0.5783 (2)0.49035 (10)0.0779 (9)
H7D0.3644310.5734520.5292440.117*
O8D0.20394 (11)0.57089 (19)0.37371 (9)0.0595 (6)
H8DA0.2539730.5677190.3786770.089*
O9D0.04418 (13)0.5987 (3)0.38052 (11)0.0855 (10)
H9D0.0617480.6035030.3455320.128*
C20D0.14259 (17)0.6320 (2)0.63629 (14)0.0491 (6)
C21D0.15698 (16)0.6176 (2)0.56629 (13)0.0454 (5)
C22D0.23806 (16)0.6060 (2)0.56353 (13)0.0532 (7)
H22D0.2813360.6085180.6048330.064*
C23D0.25414 (15)0.5905 (2)0.49910 (13)0.0500 (6)
C24D0.18962 (15)0.5872 (2)0.43739 (12)0.0460 (6)
C25D0.10842 (16)0.6009 (2)0.43992 (14)0.0534 (7)
C26D0.09230 (16)0.6162 (2)0.50474 (14)0.0528 (7)
H26D0.0382620.6254380.5068420.063*
O1W0.06378 (14)0.6137 (2)0.25269 (11)0.0731 (8)
H1WA0.1049340.5975340.2384950.110*
H1WB0.0217450.5999830.2191770.110*
O2W0.43244 (13)0.3191 (2)0.24785 (10)0.0776 (9)
H2WA0.3900010.3267470.2628870.116*
H2WB0.4731700.3247980.2844000.116*
O3W0.20277 (12)0.56091 (15)0.20812 (11)0.0539 (5)
H3WA0.1874700.5010680.1974920.081*
H3WB0.2482180.5647880.2403390.081*
O4W0.29337 (12)0.37097 (16)0.29272 (11)0.0539 (5)
H4WA0.3041950.4235780.3037970.081*
H4WB0.2524690.3728940.2559340.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0375 (7)0.1198 (16)0.0432 (8)0.0019 (9)0.0188 (6)0.0042 (9)
O1A0.0353 (8)0.1080 (18)0.0383 (9)0.0053 (10)0.0138 (7)0.0006 (10)
O2A0.0377 (8)0.0974 (16)0.0334 (8)0.0033 (9)0.0141 (7)0.0021 (9)
O3A0.0366 (9)0.1054 (18)0.0411 (9)0.0113 (10)0.0125 (7)0.0045 (10)
O4A0.0505 (10)0.0856 (16)0.0369 (9)0.0030 (10)0.0094 (7)0.0054 (9)
N1A0.0438 (10)0.0558 (13)0.0338 (9)0.0029 (9)0.0120 (8)0.0026 (9)
N2A0.0356 (9)0.0740 (15)0.0324 (9)0.0027 (9)0.0129 (7)0.0009 (9)
N3A0.0317 (9)0.0789 (16)0.0359 (10)0.0038 (9)0.0121 (8)0.0040 (10)
C1A0.0431 (13)0.098 (2)0.0359 (12)0.0032 (14)0.0108 (10)0.0051 (14)
C2A0.0353 (11)0.0662 (16)0.0366 (11)0.0008 (11)0.0124 (9)0.0016 (11)
C3A0.0394 (11)0.0731 (18)0.0340 (10)0.0078 (11)0.0121 (9)0.0012 (11)
C4A0.0386 (11)0.0679 (17)0.0384 (11)0.0001 (11)0.0163 (9)0.0024 (11)
C5A0.0368 (11)0.088 (2)0.0361 (11)0.0079 (12)0.0159 (9)0.0032 (12)
C6A0.0347 (11)0.0729 (18)0.0363 (11)0.0020 (11)0.0129 (9)0.0012 (11)
C7A0.0385 (11)0.0604 (15)0.0338 (11)0.0004 (10)0.0122 (9)0.0007 (10)
C8A0.0354 (11)0.0663 (16)0.0353 (11)0.0005 (10)0.0113 (9)0.0039 (11)
C9A0.0363 (11)0.0627 (16)0.0400 (12)0.0001 (11)0.0156 (9)0.0038 (11)
C10A0.0411 (12)0.0542 (14)0.0344 (11)0.0005 (10)0.0120 (9)0.0026 (10)
C11A0.0359 (11)0.084 (2)0.0388 (12)0.0013 (12)0.0096 (9)0.0016 (13)
C12A0.0352 (11)0.089 (2)0.0419 (13)0.0023 (12)0.0150 (10)0.0003 (13)
C13A0.0499 (14)0.0589 (16)0.0449 (13)0.0037 (12)0.0154 (11)0.0010 (12)
C14A0.0440 (13)0.086 (2)0.0409 (13)0.0028 (13)0.0147 (10)0.0049 (13)
C15A0.0594 (16)0.0725 (19)0.0385 (13)0.0027 (14)0.0080 (11)0.0066 (13)
C16A0.0480 (13)0.0657 (17)0.0370 (12)0.0089 (12)0.0091 (10)0.0017 (11)
F1B0.0520 (10)0.176 (3)0.0459 (9)0.0246 (13)0.0208 (8)0.0006 (13)
O1B0.0329 (8)0.0877 (15)0.0468 (10)0.0063 (9)0.0145 (7)0.0022 (10)
O2B0.0425 (9)0.1029 (17)0.0343 (8)0.0161 (10)0.0137 (7)0.0040 (10)
O3B0.0397 (10)0.154 (3)0.0416 (10)0.0144 (13)0.0120 (8)0.0003 (13)
O4B0.0565 (11)0.0862 (16)0.0352 (9)0.0009 (10)0.0071 (8)0.0026 (9)
N1B0.0575 (12)0.0589 (14)0.0350 (10)0.0023 (11)0.0130 (9)0.0014 (10)
N2B0.0385 (10)0.0827 (17)0.0345 (10)0.0001 (10)0.0126 (8)0.0007 (10)
N3B0.0312 (9)0.0890 (18)0.0425 (11)0.0054 (10)0.0143 (8)0.0070 (11)
C1B0.0392 (12)0.084 (2)0.0470 (14)0.0009 (13)0.0130 (11)0.0010 (14)
C2B0.0336 (10)0.0605 (15)0.0438 (12)0.0047 (10)0.0147 (9)0.0078 (11)
C3B0.0383 (11)0.0775 (19)0.0444 (13)0.0017 (12)0.0160 (10)0.0013 (12)
C4B0.0481 (13)0.0654 (17)0.0417 (12)0.0029 (12)0.0184 (10)0.0010 (11)
C5B0.0405 (12)0.093 (2)0.0396 (12)0.0036 (13)0.0151 (10)0.0016 (13)
C6B0.0409 (12)0.086 (2)0.0378 (12)0.0121 (13)0.0133 (10)0.0026 (13)
C7B0.0417 (12)0.0682 (17)0.0366 (12)0.0017 (11)0.0128 (10)0.0004 (11)
C8B0.0437 (13)0.089 (2)0.0386 (13)0.0078 (14)0.0105 (10)0.0008 (13)
C9B0.0436 (13)0.085 (2)0.0407 (13)0.0070 (13)0.0164 (11)0.0009 (13)
C10B0.0489 (13)0.0624 (17)0.0355 (12)0.0005 (12)0.0119 (10)0.0021 (11)
C11B0.0500 (15)0.100 (3)0.0402 (13)0.0135 (16)0.0089 (11)0.0039 (15)
C12B0.0439 (13)0.107 (3)0.0429 (13)0.0148 (15)0.0131 (11)0.0020 (15)
C13B0.0677 (17)0.0574 (17)0.0432 (13)0.0053 (13)0.0188 (12)0.0039 (12)
C14B0.0560 (15)0.080 (2)0.0401 (13)0.0043 (14)0.0141 (11)0.0005 (13)
C15B0.0706 (19)0.074 (2)0.0442 (14)0.0012 (16)0.0085 (13)0.0119 (14)
C16B0.0635 (17)0.0663 (19)0.0431 (13)0.0115 (14)0.0094 (12)0.0047 (13)
F1C0.0459 (9)0.193 (3)0.0477 (9)0.0131 (13)0.0236 (7)0.0012 (14)
O1C0.0367 (8)0.0816 (14)0.0423 (9)0.0049 (9)0.0122 (7)0.0037 (9)
O2C0.0367 (8)0.1033 (17)0.0346 (8)0.0037 (9)0.0130 (6)0.0015 (10)
O3C0.0319 (8)0.116 (2)0.0421 (9)0.0045 (10)0.0115 (7)0.0074 (11)
O4C0.0611 (12)0.0750 (15)0.0352 (9)0.0044 (10)0.0082 (8)0.0010 (9)
N1C0.0550 (12)0.0545 (13)0.0361 (10)0.0026 (10)0.0137 (9)0.0037 (9)
N2C0.0336 (9)0.0833 (17)0.0349 (10)0.0012 (10)0.0117 (8)0.0026 (10)
N3C0.0384 (10)0.098 (2)0.0401 (11)0.0156 (11)0.0154 (8)0.0066 (12)
C1C0.0428 (13)0.083 (2)0.0401 (13)0.0066 (13)0.0103 (10)0.0011 (13)
C2C0.0366 (11)0.0575 (14)0.0394 (11)0.0085 (10)0.0128 (9)0.0027 (10)
C3C0.0532 (14)0.099 (2)0.0393 (12)0.0223 (16)0.0161 (11)0.0102 (14)
C4C0.0382 (11)0.0789 (19)0.0403 (11)0.0001 (11)0.0152 (9)0.0051 (12)
C5C0.0361 (12)0.112 (3)0.0387 (12)0.0014 (14)0.0148 (10)0.0025 (15)
C6C0.0361 (11)0.0722 (17)0.0356 (11)0.0001 (11)0.0129 (9)0.0043 (11)
C7C0.0393 (12)0.0680 (17)0.0369 (11)0.0003 (11)0.0110 (9)0.0020 (11)
C8C0.0373 (12)0.097 (2)0.0372 (12)0.0057 (13)0.0129 (9)0.0036 (14)
C9C0.0392 (12)0.090 (2)0.0414 (13)0.0030 (13)0.0162 (10)0.0019 (13)
C1OC0.0490 (13)0.0571 (16)0.0368 (12)0.0007 (11)0.0140 (10)0.0009 (10)
C11C0.0442 (14)0.093 (2)0.0411 (13)0.0121 (15)0.0095 (11)0.0052 (15)
C12C0.0412 (13)0.101 (3)0.0432 (13)0.0097 (14)0.0154 (10)0.0053 (15)
C13C0.0627 (15)0.0559 (16)0.0437 (13)0.0026 (12)0.0183 (11)0.0017 (12)
C14C0.0555 (15)0.0696 (18)0.0396 (12)0.0010 (13)0.0145 (11)0.0025 (12)
C15C0.076 (2)0.0624 (19)0.0450 (15)0.0058 (15)0.0105 (13)0.0089 (13)
C16D0.0639 (17)0.0634 (18)0.0431 (14)0.0089 (13)0.0134 (12)0.0046 (12)
F1D0.0406 (8)0.1348 (19)0.0439 (8)0.0145 (10)0.0209 (6)0.0072 (10)
O1D0.0397 (9)0.121 (2)0.0399 (9)0.0130 (11)0.0165 (7)0.0028 (11)
O2D0.0402 (9)0.0901 (15)0.0331 (8)0.0089 (9)0.0131 (7)0.0011 (9)
O3D0.0347 (9)0.1040 (18)0.0406 (9)0.0066 (10)0.0107 (7)0.0014 (10)
O4D0.0558 (11)0.0785 (14)0.0367 (9)0.0053 (10)0.0107 (8)0.0052 (9)
N1D0.0471 (11)0.0568 (13)0.0330 (10)0.0057 (9)0.0122 (8)0.0043 (9)
N2D0.0348 (9)0.0720 (15)0.0332 (9)0.0021 (9)0.0130 (7)0.0004 (9)
N3D0.0361 (10)0.0849 (17)0.0372 (10)0.0012 (10)0.0150 (8)0.0030 (11)
C1D0.0476 (14)0.088 (2)0.0388 (13)0.0039 (14)0.0128 (11)0.0009 (13)
C2D0.0400 (12)0.0663 (17)0.0387 (12)0.0018 (11)0.0157 (10)0.0022 (11)
C3D0.0425 (12)0.0760 (19)0.0389 (11)0.0072 (12)0.0172 (9)0.0009 (12)
C4D0.0398 (11)0.0675 (17)0.0366 (11)0.0008 (11)0.0144 (9)0.0004 (11)
C5D0.0381 (12)0.088 (2)0.0358 (11)0.0027 (12)0.0153 (9)0.0006 (12)
C6D0.0371 (11)0.0644 (16)0.0358 (11)0.0039 (10)0.0125 (9)0.0021 (11)
C7D0.0376 (11)0.0571 (15)0.0348 (11)0.0016 (10)0.0115 (9)0.0021 (10)
C8D0.0346 (11)0.0713 (18)0.0365 (12)0.0053 (11)0.0100 (9)0.0041 (11)
C9D0.0371 (11)0.0699 (18)0.0377 (12)0.0064 (11)0.0154 (9)0.0058 (11)
C10D0.0435 (12)0.0543 (15)0.0336 (11)0.0031 (10)0.0131 (9)0.0037 (10)
C11D0.0402 (12)0.082 (2)0.0382 (12)0.0045 (12)0.0096 (10)0.0005 (13)
C12D0.0356 (12)0.087 (2)0.0381 (12)0.0027 (12)0.0124 (10)0.0025 (13)
C13D0.0580 (15)0.0609 (17)0.0406 (12)0.0103 (13)0.0173 (11)0.0035 (12)
C14D0.0526 (15)0.086 (2)0.0415 (13)0.0111 (14)0.0153 (11)0.0033 (14)
C15D0.0621 (16)0.0680 (19)0.0369 (12)0.0032 (14)0.0072 (11)0.0040 (12)
C10.0511 (14)0.0593 (16)0.0374 (12)0.0062 (12)0.0079 (10)0.0016 (11)
O5A0.0459 (10)0.1063 (19)0.0386 (9)0.0037 (10)0.0210 (8)0.0031 (10)
O6A0.0509 (10)0.0865 (15)0.0355 (9)0.0052 (10)0.0175 (8)0.0026 (9)
O7A0.0384 (9)0.116 (2)0.0392 (9)0.0029 (11)0.0092 (7)0.0103 (11)
O8A0.0397 (9)0.0936 (16)0.0314 (8)0.0009 (9)0.0136 (7)0.0053 (9)
O9A0.0369 (9)0.117 (2)0.0361 (9)0.0048 (10)0.0142 (7)0.0014 (11)
C20A0.0447 (12)0.0574 (15)0.0366 (12)0.0031 (10)0.0165 (10)0.0036 (10)
C21A0.0434 (12)0.0523 (14)0.0344 (11)0.0037 (10)0.0163 (9)0.0027 (10)
C22A0.0372 (11)0.0638 (16)0.0388 (12)0.0032 (11)0.0138 (9)0.0039 (11)
C23A0.0389 (11)0.0636 (16)0.0355 (11)0.0033 (11)0.0103 (9)0.0028 (11)
C24A0.0429 (12)0.0561 (14)0.0317 (11)0.0024 (10)0.0139 (9)0.0003 (10)
C25A0.0370 (11)0.0639 (16)0.0346 (11)0.0012 (10)0.0137 (9)0.0022 (10)
C26A0.0429 (12)0.0572 (15)0.0324 (11)0.0020 (10)0.0114 (9)0.0002 (10)
O5B0.0514 (11)0.1090 (19)0.0420 (10)0.0089 (11)0.0223 (8)0.0045 (11)
O6B0.0483 (10)0.127 (2)0.0362 (9)0.0007 (12)0.0151 (8)0.0113 (11)
O7B0.0388 (9)0.132 (2)0.0343 (9)0.0128 (11)0.0111 (7)0.0070 (11)
O8B0.0410 (9)0.0966 (16)0.0305 (8)0.0065 (10)0.0120 (7)0.0053 (9)
O9B0.0399 (9)0.131 (2)0.0358 (9)0.0114 (12)0.0073 (7)0.0066 (12)
C20B0.0454 (13)0.0705 (18)0.0366 (12)0.0018 (12)0.0171 (10)0.0027 (11)
C21B0.0441 (12)0.0640 (16)0.0338 (11)0.0001 (11)0.0155 (9)0.0023 (11)
C22B0.0437 (12)0.082 (2)0.0311 (11)0.0008 (12)0.0110 (9)0.0017 (12)
C23B0.0378 (12)0.0749 (18)0.0336 (11)0.0024 (11)0.0133 (9)0.0000 (11)
C24B0.0416 (12)0.0645 (16)0.0314 (11)0.0006 (11)0.0135 (9)0.0011 (11)
C25B0.0398 (12)0.0728 (18)0.0336 (11)0.0023 (11)0.0103 (9)0.0009 (11)
C26B0.0389 (12)0.0753 (18)0.0396 (12)0.0044 (12)0.0150 (9)0.0028 (12)
O5C0.0558 (11)0.0872 (16)0.0360 (9)0.0035 (10)0.0184 (8)0.0073 (9)
O6C0.0492 (10)0.1029 (18)0.0406 (9)0.0104 (11)0.0219 (8)0.0055 (11)
O7C0.0434 (10)0.1077 (19)0.0382 (9)0.0103 (11)0.0170 (8)0.0016 (11)
O8C0.0443 (9)0.0943 (16)0.0306 (8)0.0015 (10)0.0151 (7)0.0022 (9)
O9C0.0422 (9)0.124 (2)0.0387 (10)0.0010 (12)0.0115 (8)0.0069 (12)
C20C0.0509 (13)0.0522 (14)0.0388 (12)0.0066 (11)0.0186 (10)0.0023 (10)
C21C0.0485 (13)0.0495 (13)0.0358 (11)0.0053 (10)0.0191 (10)0.0031 (10)
C22C0.0472 (12)0.0560 (15)0.0355 (11)0.0012 (11)0.0155 (9)0.0008 (10)
C23C0.0452 (12)0.0572 (15)0.0349 (11)0.0021 (11)0.0162 (9)0.0018 (10)
C24C0.0433 (12)0.0579 (15)0.0308 (11)0.0042 (10)0.0151 (9)0.0029 (10)
C25C0.0415 (12)0.0650 (16)0.0352 (11)0.0039 (11)0.0120 (9)0.0015 (11)
C26C0.0421 (12)0.0642 (17)0.0398 (12)0.0071 (11)0.0167 (10)0.0037 (11)
O5D0.0529 (11)0.125 (2)0.0344 (9)0.0052 (13)0.0163 (8)0.0064 (11)
O6D0.0503 (10)0.1003 (17)0.0429 (10)0.0063 (11)0.0242 (8)0.0037 (10)
O7D0.0366 (9)0.163 (3)0.0354 (9)0.0095 (13)0.0118 (7)0.0088 (13)
O8D0.0391 (9)0.1107 (19)0.0303 (8)0.0035 (10)0.0124 (7)0.0065 (10)
O9D0.0370 (9)0.179 (3)0.0391 (10)0.0062 (14)0.0075 (8)0.0130 (15)
C20D0.0445 (12)0.0670 (17)0.0387 (12)0.0009 (11)0.0161 (10)0.0017 (11)
C21D0.0431 (12)0.0608 (15)0.0353 (11)0.0015 (11)0.0158 (9)0.0009 (11)
C22D0.0417 (12)0.086 (2)0.0323 (11)0.0025 (13)0.0113 (9)0.0036 (12)
C23D0.0373 (12)0.0787 (19)0.0355 (12)0.0033 (12)0.0127 (10)0.0014 (12)
C24D0.0414 (12)0.0686 (17)0.0304 (11)0.0002 (11)0.0138 (9)0.0026 (11)
C25D0.0374 (12)0.088 (2)0.0351 (12)0.0012 (12)0.0098 (9)0.0028 (13)
C26D0.0390 (12)0.082 (2)0.0409 (12)0.0005 (12)0.0164 (10)0.0035 (13)
O1W0.0535 (11)0.122 (2)0.0415 (10)0.0275 (14)0.0091 (9)0.0030 (12)
O2W0.0470 (10)0.150 (3)0.0340 (9)0.0199 (14)0.0082 (8)0.0002 (13)
O3W0.0424 (9)0.0723 (14)0.0444 (10)0.0017 (9)0.0070 (7)0.0050 (9)
O4W0.0440 (9)0.0713 (13)0.0421 (9)0.0011 (9)0.0045 (7)0.0042 (9)
Geometric parameters (Å, º) top
F1A—C9A1.353 (3)C13C—C14C1.509 (4)
O1A—C2A1.236 (3)C15C—C16D1.510 (4)
O2A—C4A1.442 (3)F1D—C9D1.356 (3)
O2A—C6A1.353 (3)O1D—C2D1.229 (3)
O3A—C6A1.206 (3)O2D—C4D1.450 (3)
O4A—C14A1.425 (3)O2D—C6D1.343 (3)
O4A—C15A1.432 (4)O3D—C6D1.209 (3)
N1A—C10A1.415 (3)O4D—C14D1.424 (4)
N1A—C13A1.469 (4)O4D—C15D1.433 (4)
N1A—C16A1.461 (3)N1D—C10D1.419 (3)
N2A—C5A1.455 (3)N1D—C13D1.465 (4)
N2A—C6A1.361 (3)N1D—C11.460 (3)
N2A—C7A1.418 (3)N2D—C5D1.456 (3)
N3A—C2A1.329 (3)N2D—C6D1.363 (3)
N3A—C3A1.455 (3)N2D—C7D1.421 (3)
C1A—C2A1.503 (3)N3D—C2D1.334 (3)
C3A—C4A1.503 (3)N3D—C3D1.455 (3)
C4A—C5A1.532 (3)C1D—C2D1.500 (4)
C7A—C8A1.387 (3)C3D—C4D1.500 (4)
C7A—C12A1.389 (3)C4D—C5D1.531 (3)
C8A—C9A1.368 (3)C7D—C8D1.394 (3)
C9A—C10A1.396 (3)C7D—C12D1.388 (3)
C10A—C11A1.392 (4)C8D—C9D1.368 (4)
C11A—C12A1.393 (4)C9D—C10D1.397 (3)
C13A—C14A1.511 (4)C10D—C11D1.385 (4)
C15A—C16A1.511 (4)C11D—C12D1.388 (4)
F1B—C9B1.351 (3)C13D—C14D1.517 (4)
O1B—C2B1.244 (3)C15D—C11.513 (4)
O2B—C4B1.444 (3)O5A—C20A1.301 (3)
O2B—C6B1.344 (3)O6A—C20A1.235 (3)
O3B—C6B1.202 (3)O7A—C23A1.361 (3)
O4B—C14B1.429 (4)O8A—C24A1.360 (3)
O4B—C15B1.427 (5)O9A—C25A1.357 (3)
N1B—C10B1.410 (3)C20A—C21A1.473 (3)
N1B—C13B1.466 (4)C21A—C22A1.394 (4)
N1B—C16B1.459 (4)C21A—C26A1.389 (3)
N2B—C5B1.448 (3)C22A—C23A1.387 (3)
N2B—C6B1.365 (3)C23A—C24A1.391 (3)
N2B—C7B1.417 (3)C24A—C25A1.395 (3)
N3B—C2B1.328 (3)C25A—C26A1.382 (3)
N3B—C3B1.450 (3)O5B—C20B1.300 (3)
C1B—C2B1.497 (4)O6B—C20B1.232 (3)
C3B—C4B1.490 (4)O7B—C23B1.357 (3)
C4B—C5B1.528 (4)O8B—C24B1.360 (3)
C7B—C8B1.387 (4)O9B—C25B1.358 (3)
C7B—C12B1.385 (4)C20B—C21B1.475 (3)
C8B—C9B1.367 (4)C21B—C22B1.388 (4)
C9B—C10B1.393 (4)C21B—C26B1.392 (3)
C10B—C11B1.388 (4)C22B—C23B1.376 (3)
C11B—C12B1.387 (4)C23B—C24B1.394 (3)
C13B—C14B1.506 (4)C24B—C25B1.399 (3)
C15B—C16B1.519 (4)C25B—C26B1.387 (3)
F1C—C9C1.346 (3)O5C—C20C1.247 (3)
O1C—C2C1.245 (3)O6C—C20C1.295 (3)
O2C—C4C1.440 (3)O7C—C23C1.364 (3)
O2C—C6C1.343 (3)O8C—C24C1.356 (3)
O3C—C6C1.212 (3)O9C—C25C1.354 (3)
O4C—C14C1.423 (4)C20C—C21C1.473 (3)
O4C—C15C1.430 (4)C21C—C22C1.392 (3)
N1C—C1OC1.414 (3)C21C—C26C1.386 (4)
N1C—C13C1.463 (4)C22C—C23C1.382 (3)
N1C—C16D1.454 (4)C23C—C24C1.389 (3)
N2C—C5C1.445 (3)C24C—C25C1.401 (3)
N2C—C6C1.357 (3)C25C—C26C1.384 (3)
N2C—C7C1.418 (3)O5D—C20D1.250 (3)
N3C—C2C1.321 (3)O6D—C20D1.289 (3)
N3C—C3C1.456 (3)O7D—C23D1.355 (3)
C1C—C2C1.500 (3)O8D—C24D1.357 (3)
C3C—C4C1.486 (4)O9D—C25D1.355 (3)
C4C—C5C1.534 (3)C20D—C21D1.473 (3)
C7C—C8C1.388 (4)C21D—C22D1.388 (3)
C7C—C12C1.380 (4)C21D—C26D1.387 (4)
C8C—C9C1.368 (4)C22D—C23D1.382 (3)
C9C—C1OC1.391 (4)C23D—C24D1.388 (3)
C1OC—C11C1.391 (4)C24D—C25D1.393 (3)
C11C—C12C1.388 (4)C25D—C26D1.389 (3)
C6A—O2A—C4A110.35 (18)O4C—C15C—C16D111.6 (3)
C14A—O4A—C15A109.8 (2)N1C—C16D—C15C109.0 (3)
C10A—N1A—C13A114.3 (2)C6D—O2D—C4D110.33 (18)
C10A—N1A—C16A115.9 (2)C14D—O4D—C15D109.9 (2)
C16A—N1A—C13A110.4 (2)C10D—N1D—C13D114.6 (2)
C6A—N2A—C5A111.44 (19)C10D—N1D—C1115.5 (2)
C6A—N2A—C7A125.1 (2)C1—N1D—C13D110.4 (2)
C7A—N2A—C5A123.3 (2)C6D—N2D—C5D111.33 (19)
C2A—N3A—C3A124.0 (2)C6D—N2D—C7D125.7 (2)
O1A—C2A—N3A122.4 (2)C7D—N2D—C5D122.8 (2)
O1A—C2A—C1A120.9 (2)C2D—N3D—C3D124.2 (2)
N3A—C2A—C1A116.7 (2)O1D—C2D—N3D122.3 (3)
N3A—C3A—C4A110.8 (2)O1D—C2D—C1D121.3 (2)
O2A—C4A—C3A108.5 (2)N3D—C2D—C1D116.4 (2)
O2A—C4A—C5A104.46 (18)N3D—C3D—C4D111.5 (2)
C3A—C4A—C5A114.8 (2)O2D—C4D—C3D108.5 (2)
N2A—C5A—C4A101.76 (19)O2D—C4D—C5D104.46 (19)
O2A—C6A—N2A109.7 (2)C3D—C4D—C5D114.4 (2)
O3A—C6A—O2A121.4 (2)N2D—C5D—C4D101.8 (2)
O3A—C6A—N2A128.9 (2)O2D—C6D—N2D110.1 (2)
C8A—C7A—N2A121.0 (2)O3D—C6D—O2D121.7 (2)
C8A—C7A—C12A118.5 (2)O3D—C6D—N2D128.2 (2)
C12A—C7A—N2A120.4 (2)C8D—C7D—N2D121.5 (2)
C9A—C8A—C7A119.5 (2)C12D—C7D—N2D120.3 (2)
F1A—C9A—C8A117.0 (2)C12D—C7D—C8D118.2 (2)
F1A—C9A—C10A118.7 (2)C9D—C8D—C7D119.2 (2)
C8A—C9A—C10A124.3 (2)F1D—C9D—C8D117.0 (2)
C9A—C10A—N1A119.6 (2)F1D—C9D—C10D118.3 (2)
C11A—C10A—N1A125.2 (2)C8D—C9D—C10D124.6 (2)
C11A—C10A—C9A115.1 (2)C9D—C10D—N1D119.5 (2)
C10A—C11A—C12A122.0 (2)C11D—C10D—N1D125.7 (2)
C7A—C12A—C11A120.6 (2)C11D—C10D—C9D114.8 (2)
N1A—C13A—C14A110.2 (3)C10D—C11D—C12D122.4 (2)
O4A—C14A—C13A110.9 (2)C11D—C12D—C7D120.9 (2)
O4A—C15A—C16A110.8 (3)N1D—C13D—C14D109.7 (3)
N1A—C16A—C15A109.1 (2)O4D—C14D—C13D111.0 (2)
C6B—O2B—C4B110.2 (2)O4D—C15D—C1111.0 (3)
C15B—O4B—C14B111.3 (2)N1D—C1—C15D108.9 (2)
C10B—N1B—C13B114.8 (2)O5A—C20A—C21A115.8 (2)
C10B—N1B—C16B116.2 (2)O6A—C20A—O5A122.6 (2)
C16B—N1B—C13B109.9 (2)O6A—C20A—C21A121.6 (2)
C6B—N2B—C5B111.5 (2)C22A—C21A—C20A121.0 (2)
C6B—N2B—C7B125.4 (2)C26A—C21A—C20A118.5 (2)
C7B—N2B—C5B122.9 (2)C26A—C21A—C22A120.5 (2)
C2B—N3B—C3B124.8 (2)C23A—C22A—C21A119.6 (2)
O1B—C2B—N3B122.1 (2)O7A—C23A—C22A118.5 (2)
O1B—C2B—C1B121.0 (2)O7A—C23A—C24A121.5 (2)
N3B—C2B—C1B116.9 (2)C22A—C23A—C24A120.0 (2)
N3B—C3B—C4B111.4 (2)O8A—C24A—C23A117.8 (2)
O2B—C4B—C3B108.6 (2)O8A—C24A—C25A122.1 (2)
O2B—C4B—C5B104.47 (19)C23A—C24A—C25A120.0 (2)
C3B—C4B—C5B114.6 (3)O9A—C25A—C24A115.8 (2)
N2B—C5B—C4B101.6 (2)O9A—C25A—C26A124.2 (2)
O2B—C6B—N2B109.6 (2)C26A—C25A—C24A120.0 (2)
O3B—C6B—O2B122.0 (2)C25A—C26A—C21A119.8 (2)
O3B—C6B—N2B128.4 (2)O5B—C20B—C21B116.5 (2)
C8B—C7B—N2B121.5 (2)O6B—C20B—O5B122.6 (2)
C12B—C7B—N2B119.9 (2)O6B—C20B—C21B120.9 (2)
C12B—C7B—C8B118.6 (2)C22B—C21B—C20B117.7 (2)
C9B—C8B—C7B119.1 (3)C22B—C21B—C26B120.4 (2)
F1B—C9B—C8B117.2 (3)C26B—C21B—C20B121.9 (2)
F1B—C9B—C10B118.3 (2)C23B—C22B—C21B119.9 (2)
C8B—C9B—C10B124.5 (3)O7B—C23B—C22B125.2 (2)
C9B—C10B—N1B119.7 (2)O7B—C23B—C24B114.5 (2)
C11B—C10B—N1B125.2 (3)C22B—C23B—C24B120.3 (2)
C11B—C10B—C9B115.0 (2)O8B—C24B—C23B121.6 (2)
C12B—C11B—C10B122.0 (3)O8B—C24B—C25B118.4 (2)
C7B—C12B—C11B120.7 (3)C23B—C24B—C25B120.0 (2)
N1B—C13B—C14B109.4 (3)O9B—C25B—C24B121.7 (2)
O4B—C14B—C13B110.6 (2)O9B—C25B—C26B118.8 (2)
O4B—C15B—C16B111.8 (3)C26B—C25B—C24B119.5 (2)
N1B—C16B—C15B108.1 (3)C25B—C26B—C21B119.9 (2)
C6C—O2C—C4C110.70 (19)O5C—C20C—O6C122.4 (2)
C14C—O4C—C15C111.0 (2)O5C—C20C—C21C120.8 (2)
C1OC—N1C—C13C114.2 (2)O6C—C20C—C21C116.6 (2)
C1OC—N1C—C16D116.6 (2)C22C—C21C—C20C118.1 (2)
C16D—N1C—C13C109.6 (2)C26C—C21C—C20C121.0 (2)
C6C—N2C—C5C112.1 (2)C26C—C21C—C22C120.7 (2)
C6C—N2C—C7C125.5 (2)C23C—C22C—C21C119.3 (2)
C7C—N2C—C5C122.4 (2)O7C—C23C—C22C123.8 (2)
C2C—N3C—C3C123.7 (2)O7C—C23C—C24C115.7 (2)
O1C—C2C—N3C122.4 (2)C22C—C23C—C24C120.5 (2)
O1C—C2C—C1C120.8 (2)O8C—C24C—C23C122.4 (2)
N3C—C2C—C1C116.8 (2)O8C—C24C—C25C117.9 (2)
N3C—C3C—C4C112.7 (3)C23C—C24C—C25C119.8 (2)
O2C—C4C—C3C109.1 (3)O9C—C25C—C24C121.6 (2)
O2C—C4C—C5C105.01 (19)O9C—C25C—C26C118.7 (2)
C3C—C4C—C5C113.0 (3)C26C—C25C—C24C119.8 (2)
N2C—C5C—C4C102.1 (2)C25C—C26C—C21C119.9 (2)
O2C—C6C—N2C110.0 (2)O5D—C20D—O6D122.2 (2)
O3C—C6C—O2C121.5 (2)O5D—C20D—C21D120.1 (2)
O3C—C6C—N2C128.5 (2)O6D—C20D—C21D117.7 (2)
C8C—C7C—N2C121.0 (2)C22D—C21D—C20D117.8 (2)
C12C—C7C—N2C120.4 (2)C26D—C21D—C20D121.7 (2)
C12C—C7C—C8C118.5 (3)C26D—C21D—C22D120.5 (2)
C9C—C8C—C7C119.4 (3)C23D—C22D—C21D119.7 (2)
F1C—C9C—C8C117.1 (2)O7D—C23D—C22D124.5 (2)
F1C—C9C—C1OC118.8 (2)O7D—C23D—C24D115.3 (2)
C8C—C9C—C1OC124.1 (2)C22D—C23D—C24D120.2 (2)
C9C—C1OC—N1C119.8 (2)O8D—C24D—C23D121.1 (2)
C9C—C1OC—C11C115.3 (2)O8D—C24D—C25D118.7 (2)
C11C—C1OC—N1C124.9 (2)C23D—C24D—C25D120.2 (2)
C12C—C11C—C1OC121.8 (3)O9D—C25D—C24D121.6 (2)
C7C—C12C—C11C120.8 (3)O9D—C25D—C26D118.9 (2)
N1C—C13C—C14C110.2 (3)C26D—C25D—C24D119.6 (2)
O4C—C14C—C13C110.6 (2)C21D—C26D—C25D119.8 (2)
 

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