Structural variety of heterosynthons in linezolid cocrystals with modified thermal properties

Khalaji, M.; Wróblewska, A.; Wielgus, E.; Bujacz, G.D.; Dudek, M.K.; Potrzebowski, M.J.

doi:10.1107/S2052520620010896

Structural variety of heterosynthons in linezolid cocrystals with modified thermal properties

M. Khalaji, A. Wróblewska, E. Wielgus, G. D. Bujacz, M. K. Dudek and M. J. Potrzebowski

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=O_amide > C=O_oxazolidone > C—O—C_morpholine > C—N—C_morpholine > C—O—C_oxazolidone. 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.

Keywords: linezolid; cocrystals; X-ray diffraction; supramolecular synthons; thermal properties.

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Supporting information

	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
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_BAsup2.hkl Contains datablock LIN:BA
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_PHBA_H2Osup3.hkl Contains datablock LIN:PHBA:H2O
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_26DHBAsup4.hkl Contains datablock LIN:2,6DHBA
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_34DHBA_H2Osup5.hkl Contains datablock LIN:3,4-DHBA:H2O
	Structure factor file (CIF format) https://doi.org/10.1107/S2052520620010896/xk5072LIN_GA_H2Osup6.hkl Contains datablock LIN:GA:H2O
	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·C₇H₆O₂	F(000) = 484
M_r = 459.47	D_x = 1.344 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 6.49617 (9) Å	Cell parameters from 12111 reflections
b = 7.41888 (18) Å	θ = 3.7–74.0°
c = 23.5870 (4) Å	µ = 0.87 mm⁻¹
β = 92.9418 (13)°	T = 293 K
V = 1135.26 (4) Å³	Plate
Z = 2	0.63 × 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 Source	4032 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.048
Detector resolution: 4.1685 pixels mm^-1	θ_max = 74.6°, θ_min = 3.8°
ω scans	h = −8→8
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 = −7→9
T_min = 0.211, T_max = 1.000	l = −29→29
18906 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.060P)² + 0.1176P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.037	(Δ/σ)_max < 0.001
wR(F²) = 0.103	Δρ_max = 0.18 e Å⁻³
S = 1.03	Δρ_min = −0.15 e Å⁻³
4213 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
301 parameters	Extinction coefficient: 0.0069 (9)
1 restraint	Absolute 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 methods	Absolute 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

	x	y	z	U_iso*/U_eq
F1	0.8098 (2)	0.0263 (3)	0.37441 (6)	0.0757 (6)
O1	1.1815 (3)	0.1503 (3)	−0.03789 (7)	0.0567 (5)
O2	0.8084 (2)	0.0386 (3)	0.09854 (6)	0.0557 (5)
O3	0.6319 (2)	0.0236 (4)	0.17727 (7)	0.0723 (6)
O4	1.3193 (3)	−0.2396 (3)	0.52246 (7)	0.0611 (5)
N1	1.1857 (3)	−0.0958 (3)	0.41515 (7)	0.0469 (4)
N2	0.9891 (2)	0.0082 (3)	0.18053 (7)	0.0458 (4)
N3	1.2685 (3)	0.2661 (3)	0.04742 (8)	0.0512 (5)
H3	1.365081	0.309132	0.069774	0.061*
C1	1.5239 (4)	0.2683 (4)	−0.02290 (12)	0.0583 (6)
H1A	1.592107	0.159787	−0.033733	0.087*
H1B	1.600958	0.323760	0.008243	0.087*
H1C	1.514679	0.349920	−0.054511	0.087*
C2	1.3119 (3)	0.2239 (3)	−0.00528 (9)	0.0463 (5)
C3	1.0648 (3)	0.2426 (4)	0.06899 (10)	0.0538 (6)
H3A	0.961950	0.282315	0.040416	0.065*
H3B	1.052705	0.317886	0.102286	0.065*
C4	1.0218 (3)	0.0495 (4)	0.08447 (8)	0.0474 (5)
H4	1.046902	−0.029933	0.052345	0.057*
C5	1.1409 (3)	−0.0176 (4)	0.13777 (9)	0.0521 (6)
H5A	1.178884	−0.143448	0.134409	0.063*
H5B	1.263890	0.053714	0.146120	0.063*
C6	0.7953 (3)	0.0230 (4)	0.15563 (9)	0.0497 (6)
C7	1.0362 (3)	−0.0221 (4)	0.23911 (8)	0.0427 (5)
C8	0.8930 (3)	0.0147 (4)	0.27972 (9)	0.0499 (6)
H8	0.762322	0.057886	0.269089	0.060*
C9	0.9505 (3)	−0.0146 (4)	0.33572 (9)	0.0493 (5)
C10	1.1416 (3)	−0.0778 (3)	0.35581 (9)	0.0438 (5)
C11	1.2807 (3)	−0.1108 (4)	0.31413 (10)	0.0516 (6)
H11	1.411943	−0.152454	0.324972	0.062*
C12	1.2303 (3)	−0.0837 (4)	0.25703 (9)	0.0520 (6)
H12	1.327598	−0.106969	0.230405	0.062*
C13	1.0720 (4)	−0.2387 (4)	0.44223 (9)	0.0554 (6)
H13A	1.117601	−0.355103	0.428954	0.066*
H13B	0.926058	−0.226863	0.432019	0.066*
C14	1.1067 (4)	−0.2279 (4)	0.50611 (10)	0.0563 (6)
H14A	1.052014	−0.114904	0.519538	0.068*
H14B	1.033264	−0.325396	0.523599	0.068*
C15	1.4274 (4)	−0.0981 (5)	0.49661 (11)	0.0637 (7)
H15A	1.572422	−0.105462	0.508396	0.076*
H15B	1.375618	0.016830	0.509394	0.076*
C16	1.4041 (3)	−0.1069 (5)	0.43263 (10)	0.0562 (6)
H16A	1.478240	−0.007849	0.416208	0.067*
H16B	1.461309	−0.219007	0.419327	0.067*
O5	0.4790 (4)	0.4826 (5)	0.13067 (9)	0.0963 (9)
O6	0.7952 (3)	0.5871 (4)	0.14655 (8)	0.0734 (6)
H6	0.786968	0.600716	0.112009	0.110*
C20	0.6229 (5)	0.5174 (4)	0.16323 (11)	0.0630 (7)
C21	0.6165 (5)	0.4860 (4)	0.22522 (11)	0.0655 (7)
C22	0.4394 (7)	0.4130 (6)	0.24595 (16)	0.0864 (10)
H22	0.326694	0.387848	0.221303	0.104*
C23	0.4299 (10)	0.3773 (7)	0.30342 (18)	0.1100 (16)
H23	0.310610	0.328486	0.317316	0.132*
C24	0.5939 (12)	0.4133 (7)	0.33940 (16)	0.120 (2)
H24	0.587867	0.386674	0.377807	0.144*
C25	0.7684 (11)	0.4886 (7)	0.31953 (16)	0.1200 (19)
H25	0.878741	0.515493	0.344795	0.144*
C26	0.7830 (7)	0.5258 (6)	0.26179 (14)	0.0896 (11)
H26	0.902181	0.576140	0.248321	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0516 (7)	0.1330 (17)	0.0441 (7)	0.0246 (10)	0.0176 (6)	0.0012 (9)
O1	0.0538 (8)	0.0702 (12)	0.0460 (8)	−0.0139 (8)	0.0027 (6)	−0.0036 (8)
O2	0.0358 (7)	0.0908 (14)	0.0403 (7)	−0.0044 (8)	0.0010 (5)	−0.0012 (8)
O3	0.0330 (7)	0.130 (2)	0.0546 (9)	−0.0008 (10)	0.0070 (6)	0.0036 (11)
O4	0.0702 (10)	0.0698 (13)	0.0430 (8)	0.0009 (9)	0.0003 (7)	0.0064 (8)
N1	0.0435 (8)	0.0593 (12)	0.0385 (8)	−0.0043 (9)	0.0063 (7)	0.0049 (9)
N2	0.0327 (7)	0.0681 (13)	0.0370 (8)	0.0015 (8)	0.0070 (6)	0.0020 (8)
N3	0.0461 (9)	0.0626 (14)	0.0447 (9)	−0.0086 (9)	−0.0002 (7)	−0.0039 (9)
C1	0.0481 (12)	0.0639 (17)	0.0635 (13)	−0.0064 (12)	0.0083 (10)	0.0016 (12)
C2	0.0465 (11)	0.0468 (13)	0.0457 (10)	−0.0027 (9)	0.0023 (8)	0.0023 (9)
C3	0.0468 (11)	0.0682 (17)	0.0468 (11)	0.0034 (11)	0.0062 (9)	−0.0015 (11)
C4	0.0384 (9)	0.0675 (16)	0.0368 (9)	−0.0014 (10)	0.0056 (7)	−0.0028 (10)
C5	0.0375 (9)	0.0789 (18)	0.0406 (10)	0.0057 (10)	0.0095 (8)	0.0043 (11)
C6	0.0358 (9)	0.0719 (17)	0.0416 (10)	−0.0028 (11)	0.0041 (7)	−0.0003 (11)
C7	0.0354 (8)	0.0558 (14)	0.0374 (9)	−0.0014 (8)	0.0065 (7)	0.0024 (9)
C8	0.0371 (9)	0.0703 (17)	0.0430 (10)	0.0063 (10)	0.0085 (8)	0.0008 (11)
C9	0.0387 (9)	0.0685 (16)	0.0418 (10)	0.0028 (10)	0.0132 (8)	0.0017 (10)
C10	0.0406 (9)	0.0518 (14)	0.0397 (10)	−0.0009 (9)	0.0075 (7)	0.0041 (9)
C11	0.0387 (10)	0.0724 (17)	0.0442 (11)	0.0082 (11)	0.0072 (8)	0.0084 (11)
C12	0.0398 (10)	0.0750 (17)	0.0419 (10)	0.0084 (11)	0.0105 (8)	0.0052 (11)
C13	0.0604 (13)	0.0628 (17)	0.0433 (11)	−0.0144 (12)	0.0052 (9)	0.0059 (11)
C14	0.0662 (14)	0.0600 (16)	0.0433 (11)	−0.0075 (13)	0.0091 (10)	0.0046 (11)
C15	0.0580 (13)	0.085 (2)	0.0475 (12)	−0.0125 (14)	−0.0032 (10)	0.0046 (14)
C16	0.0454 (11)	0.0777 (19)	0.0455 (11)	−0.0053 (12)	0.0033 (8)	0.0066 (12)
O5	0.1120 (18)	0.121 (2)	0.0533 (10)	−0.0467 (17)	−0.0176 (11)	0.0036 (13)
O6	0.0747 (12)	0.0943 (17)	0.0505 (10)	0.0001 (11)	−0.0024 (8)	0.0011 (11)
C20	0.0835 (17)	0.0590 (17)	0.0459 (12)	−0.0054 (15)	−0.0041 (11)	−0.0053 (12)
C21	0.096 (2)	0.0550 (17)	0.0450 (12)	−0.0017 (15)	−0.0025 (12)	−0.0045 (11)
C22	0.116 (3)	0.078 (2)	0.0666 (18)	−0.005 (2)	0.0136 (18)	0.0042 (18)
C23	0.176 (5)	0.089 (3)	0.068 (2)	0.006 (3)	0.039 (3)	0.008 (2)
C24	0.233 (7)	0.078 (3)	0.0503 (18)	0.018 (4)	0.015 (3)	0.0064 (19)
C25	0.206 (6)	0.094 (3)	0.0548 (18)	0.005 (4)	−0.042 (3)	−0.008 (2)
C26	0.133 (3)	0.076 (2)	0.0565 (16)	−0.011 (2)	−0.0250 (17)	−0.0026 (16)

Geometric parameters (Å, º) top

F1—C9	1.359 (2)	C7—C8	1.396 (3)
O1—C2	1.241 (3)	C7—C12	1.386 (3)
O2—C4	1.444 (2)	C8—C9	1.372 (3)
O2—C6	1.358 (3)	C9—C10	1.387 (3)
O3—C6	1.202 (3)	C10—C11	1.391 (3)
O4—C14	1.417 (3)	C11—C12	1.384 (3)
O4—C15	1.418 (4)	C13—C14	1.514 (3)
N1—C10	1.420 (3)	C15—C16	1.510 (3)
N1—C13	1.458 (3)	O5—C20	1.207 (4)
N1—C16	1.459 (3)	O6—C20	1.312 (4)
N2—C5	1.459 (2)	C20—C21	1.483 (4)
N2—C6	1.366 (3)	C21—C22	1.384 (5)
N2—C7	1.418 (3)	C21—C26	1.380 (5)
N3—C2	1.326 (3)	C22—C23	1.386 (5)
N3—C3	1.453 (3)	C23—C24	1.354 (8)
C1—C2	1.495 (3)	C24—C25	1.368 (8)
C3—C4	1.508 (4)	C25—C26	1.398 (5)
C4—C5	1.525 (3)

C6—O2—C4	110.02 (15)	F1—C9—C8	116.88 (19)
C14—O4—C15	109.6 (2)	F1—C9—C10	117.86 (19)
C10—N1—C13	114.77 (18)	C8—C9—C10	125.24 (18)
C10—N1—C16	115.33 (16)	C9—C10—N1	119.99 (18)
C13—N1—C16	110.0 (2)	C9—C10—C11	114.88 (19)
C6—N2—C5	110.73 (16)	C11—C10—N1	125.05 (19)
C6—N2—C7	125.44 (16)	C12—C11—C10	122.1 (2)
C7—N2—C5	122.21 (17)	C11—C12—C7	120.72 (19)
C2—N3—C3	122.78 (19)	N1—C13—C14	110.1 (2)
O1—C2—N3	120.9 (2)	O4—C14—C13	111.1 (2)
O1—C2—C1	122.3 (2)	O4—C15—C16	111.8 (2)
N3—C2—C1	116.8 (2)	N1—C16—C15	109.04 (19)
N3—C3—C4	112.4 (2)	O5—C20—O6	122.6 (3)
O2—C4—C3	107.5 (2)	O5—C20—C21	122.3 (3)
O2—C4—C5	104.15 (16)	O6—C20—C21	115.1 (2)
C3—C4—C5	114.7 (2)	C22—C21—C20	118.4 (3)
N2—C5—C4	101.23 (16)	C26—C21—C20	121.5 (3)
O2—C6—N2	109.25 (16)	C26—C21—C22	120.2 (3)
O3—C6—O2	121.50 (19)	C21—C22—C23	120.0 (4)
O3—C6—N2	129.2 (2)	C24—C23—C22	120.1 (5)
C8—C7—N2	121.30 (19)	C23—C24—C25	120.3 (4)
C12—C7—N2	119.80 (17)	C24—C25—C26	120.9 (4)
C12—C7—C8	118.87 (19)	C21—C26—C25	118.4 (4)
C9—C8—C7	118.15 (19)

(LIN:PHBA:H2O) top

Crystal data top

C₁₆H₂₀FN₃O₄·C₇H₆O₃·H₂O	D_x = 1.401 Mg m⁻³
M_r = 492.47	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4747 reflections
a = 6.428 (3) Å	θ = 3.3–73.9°
b = 6.987 (3) Å	µ = 0.95 mm⁻¹
c = 52.001 (9) Å	T = 100 K
V = 2335.5 (15) Å³	Needle, colourless
Z = 4	0.5 × 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 Source	6511 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.187
Detector resolution: 8.3370 pixels mm^-1	θ_max = 67.5°, θ_min = 3.4°
ω scans	h = −7→7
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 = −8→8
T_min = 0.809, T_max = 1.000	l = −61→62
8325 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.2P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.143	(Δ/σ)_max = 0.002
wR(F²) = 0.397	Δρ_max = 1.48 e Å⁻³
S = 1.65	Δρ_min = −0.82 e Å⁻³
8325 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
320 parameters	Extinction coefficient: 0.031 (10)
0 restraints	Absolute structure: Classical Flack method preferred over Parsons because s.u. lower.
Hydrogen site location: mixed	Absolute structure parameter: 1.5 (6)

Special details top

Refinement. Refined as a 4-component twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	1.7514 (13)	1.5372 (16)	1.07772 (15)	0.058 (3)
O1	1.3158 (12)	1.6111 (14)	1.26644 (15)	0.036 (2)
O2	1.7047 (12)	1.4987 (14)	1.20233 (15)	0.0351 (19)
O3	1.8963 (12)	1.503 (2)	1.16661 (16)	0.046 (3)
O4	1.174 (2)	1.482 (3)	1.0103 (2)	0.079 (5)
N1	1.3736 (18)	1.426 (2)	1.0588 (2)	0.044 (3)
N2	1.5314 (13)	1.4895 (18)	1.16499 (18)	0.035 (2)
N3	1.2295 (16)	1.7311 (17)	1.22775 (18)	0.035 (2)
H3	1.130019	1.770347	1.217387	0.042*
C1	0.9664 (18)	1.7376 (19)	1.2609 (2)	0.036 (3)
H1A	0.973622	1.830801	1.274924	0.054*
H1B	0.899687	1.620127	1.267031	0.054*
H1C	0.884910	1.791293	1.246663	0.054*
C2	1.1834 (17)	1.6924 (18)	1.2516 (2)	0.032 (2)
C3	1.4407 (18)	1.7118 (19)	1.2176 (2)	0.034 (3)
H3A	1.541646	1.749768	1.231017	0.041*
H3B	1.458135	1.799969	1.202818	0.041*
C4	1.4879 (16)	1.511 (2)	1.2090 (2)	0.037 (3)
H4	1.457503	1.420062	1.223356	0.044*
C5	1.3735 (15)	1.444 (2)	1.1846 (2)	0.036 (3)
H5A	1.342013	1.305717	1.185145	0.043*
H5B	1.243342	1.517106	1.181795	0.043*
C6	1.7275 (16)	1.4946 (16)	1.1772 (2)	0.032 (2)
C7	1.4954 (15)	1.4745 (19)	1.1393 (2)	0.0341 (19)
C8	1.6487 (15)	1.5209 (19)	1.1204 (2)	0.0341 (19)
H8	1.782821	1.564393	1.125402	0.041*
C9	1.5994 (18)	1.502 (2)	1.0958 (2)	0.041 (3)
C10	1.4046 (18)	1.439 (2)	1.0856 (2)	0.041 (3)
C11	1.256 (2)	1.396 (2)	1.1047 (2)	0.040 (3)
H11	1.121288	1.356507	1.099509	0.049*
C12	1.299 (2)	1.407 (2)	1.1304 (2)	0.043 (3)
H12	1.196268	1.369906	1.142500	0.051*
C13	1.380 (3)	1.612 (3)	1.0453 (3)	0.057 (4)
H13A	1.263602	1.692553	1.051547	0.069*
H13B	1.511552	1.677682	1.049539	0.069*
C14	1.363 (4)	1.590 (3)	1.0175 (3)	0.070 (5)
H14A	1.487364	1.521352	1.010942	0.084*
H14B	1.359776	1.717925	1.009320	0.084*
C15	1.159 (3)	1.310 (4)	1.0237 (3)	0.073 (6)
H15A	1.270786	1.223324	1.017640	0.088*
H15B	1.024237	1.249169	1.019578	0.088*
C16	1.176 (3)	1.331 (3)	1.0521 (3)	0.055 (4)
H16A	1.057953	1.407163	1.058603	0.066*
H16B	1.171049	1.202988	1.060254	0.066*
O5	1.0381 (15)	1.9498 (17)	1.18910 (17)	0.048 (2)
O6	0.7177 (14)	2.0584 (16)	1.18422 (15)	0.043 (2)
H6	0.719256	2.050330	1.200332	0.065*
O7	0.9517 (19)	1.9275 (19)	1.06833 (17)	0.053 (3)
H7	0.834341	1.927591	1.061219	0.080*
C20	0.892 (2)	1.993 (2)	1.1750 (2)	0.042 (3)
C21	0.9025 (19)	1.975 (2)	1.1475 (2)	0.039 (3)
C22	0.731 (2)	2.022 (2)	1.1311 (2)	0.040 (3)
H22	0.603182	2.063148	1.138487	0.048*
C23	0.748 (2)	2.008 (2)	1.1055 (3)	0.044 (3)
H23	0.632519	2.044067	1.095058	0.053*
C24	0.928 (2)	1.9440 (17)	1.0936 (3)	0.042 (3)
C25	1.098 (2)	1.892 (2)	1.1097 (3)	0.047 (3)
H25	1.223434	1.847178	1.102142	0.057*
C26	1.083 (2)	1.906 (2)	1.1350 (3)	0.045 (3)
H26	1.198424	1.868122	1.145219	0.054*
O1W	1.643 (3)	1.102 (3)	1.0427 (2)	0.085 (5)
H1WA	1.564672	1.187035	1.050036	0.127*
H1WB	1.583649	1.080269	1.028015	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.031 (4)	0.082 (8)	0.062 (5)	−0.016 (5)	0.011 (3)	−0.004 (4)
O1	0.013 (3)	0.040 (5)	0.054 (5)	0.002 (4)	−0.003 (3)	0.001 (3)
O2	0.013 (4)	0.037 (5)	0.056 (5)	0.002 (4)	−0.002 (3)	0.006 (3)
O3	0.012 (4)	0.073 (8)	0.054 (5)	0.007 (5)	0.003 (3)	0.003 (4)
O4	0.076 (9)	0.111 (14)	0.051 (6)	0.021 (10)	−0.014 (5)	−0.007 (6)
N1	0.024 (5)	0.047 (7)	0.062 (6)	−0.004 (5)	0.003 (4)	0.001 (5)
N2	0.007 (4)	0.044 (6)	0.053 (5)	−0.006 (5)	0.003 (3)	−0.002 (4)
N3	0.023 (5)	0.040 (6)	0.044 (5)	0.008 (5)	−0.004 (4)	−0.008 (4)
C1	0.014 (5)	0.032 (6)	0.063 (7)	0.012 (5)	0.000 (4)	−0.001 (5)
C2	0.015 (5)	0.028 (6)	0.054 (6)	0.007 (4)	−0.003 (4)	−0.009 (4)
C3	0.021 (5)	0.039 (7)	0.041 (5)	0.001 (5)	0.004 (4)	−0.001 (4)
C4	0.014 (5)	0.047 (8)	0.049 (6)	0.001 (6)	0.002 (4)	−0.004 (5)
C5	0.003 (4)	0.049 (7)	0.054 (6)	−0.008 (5)	0.004 (4)	−0.005 (5)
C6	0.009 (4)	0.012 (4)	0.074 (7)	−0.003 (4)	−0.010 (4)	0.002 (4)
C7	0.006 (3)	0.034 (5)	0.062 (5)	−0.004 (3)	0.005 (3)	0.002 (3)
C8	0.006 (3)	0.034 (5)	0.062 (5)	−0.004 (3)	0.005 (3)	0.002 (3)
C9	0.013 (5)	0.047 (8)	0.064 (7)	0.001 (6)	0.012 (4)	0.008 (6)
C10	0.011 (5)	0.053 (9)	0.059 (7)	−0.004 (6)	0.005 (4)	0.000 (5)
C11	0.022 (6)	0.042 (8)	0.058 (7)	−0.002 (6)	0.003 (5)	−0.003 (5)
C12	0.022 (5)	0.056 (9)	0.051 (6)	−0.005 (6)	0.003 (4)	−0.002 (5)
C13	0.067 (11)	0.044 (9)	0.061 (8)	0.009 (9)	0.005 (7)	0.001 (6)
C14	0.075 (13)	0.067 (12)	0.067 (9)	0.007 (11)	−0.002 (8)	0.002 (8)
C15	0.059 (11)	0.096 (18)	0.064 (10)	−0.018 (12)	0.005 (7)	−0.006 (9)
C16	0.036 (7)	0.059 (11)	0.070 (9)	−0.011 (8)	−0.001 (6)	−0.009 (7)
O5	0.031 (5)	0.056 (7)	0.056 (5)	0.005 (5)	−0.005 (4)	0.005 (4)
O6	0.031 (4)	0.055 (6)	0.043 (4)	−0.005 (4)	0.000 (3)	−0.001 (3)
O7	0.051 (6)	0.059 (7)	0.049 (5)	0.004 (6)	0.002 (4)	0.004 (4)
C20	0.027 (6)	0.032 (7)	0.067 (7)	0.004 (6)	−0.007 (5)	0.003 (5)
C21	0.020 (5)	0.033 (7)	0.063 (7)	0.013 (6)	−0.001 (5)	0.004 (5)
C22	0.033 (6)	0.029 (6)	0.059 (7)	0.004 (6)	−0.003 (5)	0.001 (5)
C23	0.030 (6)	0.033 (7)	0.069 (8)	0.004 (6)	−0.006 (5)	0.001 (5)
C24	0.025 (6)	0.009 (5)	0.093 (9)	0.004 (5)	0.001 (6)	0.004 (5)
C25	0.031 (7)	0.036 (8)	0.075 (9)	−0.008 (7)	0.008 (6)	0.003 (6)
C26	0.028 (6)	0.036 (8)	0.070 (8)	−0.001 (6)	0.004 (5)	−0.001 (6)
O1W	0.096 (11)	0.111 (13)	0.047 (6)	0.041 (10)	0.000 (6)	−0.001 (6)

Geometric parameters (Å, º) top

F1—C9	1.378 (13)	C10—C11	1.408 (17)
O1—C2	1.282 (14)	C11—H11	0.9500
O2—C4	1.438 (12)	C11—C12	1.365 (18)
O2—C6	1.317 (14)	C12—H12	0.9500
O3—C6	1.218 (14)	C13—H13A	0.9900
O4—C14	1.48 (3)	C13—H13B	0.9900
O4—C15	1.39 (3)	C13—C14	1.46 (2)
N1—C10	1.414 (18)	C14—H14A	0.9900
N1—C13	1.47 (2)	C14—H14B	0.9900
N1—C16	1.474 (19)	C15—H15A	0.9900
N2—C5	1.473 (13)	C15—H15B	0.9900
N2—C6	1.411 (13)	C15—C16	1.49 (2)
N2—C7	1.360 (16)	C16—H16A	0.9900
N3—H3	0.8800	C16—H16B	0.9900
N3—C2	1.304 (16)	O5—C20	1.228 (16)
N3—C3	1.463 (15)	O6—H6	0.8400
C1—H1A	0.9800	O6—C20	1.303 (17)
C1—H1B	0.9800	O7—H7	0.8400
C1—H1C	0.9800	O7—C24	1.328 (17)
C1—C2	1.509 (15)	C20—C21	1.437 (19)
C3—H3A	0.9900	C21—C22	1.433 (17)
C3—H3B	0.9900	C21—C26	1.414 (18)
C3—C4	1.504 (19)	C22—H22	0.9500
C4—H4	1.0000	C22—C23	1.341 (18)
C4—C5	1.537 (16)	C23—H23	0.9500
C5—H5A	0.9900	C23—C24	1.388 (19)
C5—H5B	0.9900	C24—C25	1.42 (2)
C7—C8	1.428 (14)	C25—H25	0.9500
C7—C12	1.423 (16)	C25—C26	1.33 (2)
C8—H8	0.9500	C26—H26	0.9500
C8—C9	1.327 (19)	O1W—H1WA	0.8693
C9—C10	1.427 (17)	O1W—H1WB	0.8673

C6—O2—C4	110.4 (8)	C12—C11—C10	122.6 (12)
C15—O4—C14	111.5 (14)	C12—C11—H11	118.7
C10—N1—C13	114.1 (13)	C7—C12—H12	119.5
C10—N1—C16	112.6 (11)	C11—C12—C7	121.1 (12)
C13—N1—C16	107.9 (14)	C11—C12—H12	119.5
C6—N2—C5	108.1 (9)	N1—C13—H13A	109.2
C7—N2—C5	123.1 (9)	N1—C13—H13B	109.2
C7—N2—C6	126.5 (9)	H13A—C13—H13B	107.9
C2—N3—H3	118.8	C14—C13—N1	112.2 (16)
C2—N3—C3	122.4 (9)	C14—C13—H13A	109.2
C3—N3—H3	118.8	C14—C13—H13B	109.2
H1A—C1—H1B	109.5	O4—C14—H14A	109.4
H1A—C1—H1C	109.5	O4—C14—H14B	109.4
H1B—C1—H1C	109.5	C13—C14—O4	111.2 (16)
C2—C1—H1A	109.5	C13—C14—H14A	109.4
C2—C1—H1B	109.5	C13—C14—H14B	109.4
C2—C1—H1C	109.5	H14A—C14—H14B	108.0
O1—C2—N3	120.9 (10)	O4—C15—H15A	108.7
O1—C2—C1	121.0 (10)	O4—C15—H15B	108.7
N3—C2—C1	118.1 (10)	O4—C15—C16	114 (2)
N3—C3—H3A	109.1	H15A—C15—H15B	107.6
N3—C3—H3B	109.1	C16—C15—H15A	108.7
N3—C3—C4	112.4 (10)	C16—C15—H15B	108.7
H3A—C3—H3B	107.9	N1—C16—C15	110.1 (14)
C4—C3—H3A	109.1	N1—C16—H16A	109.6
C4—C3—H3B	109.1	N1—C16—H16B	109.6
O2—C4—C3	108.8 (11)	C15—C16—H16A	109.6
O2—C4—H4	109.3	C15—C16—H16B	109.6
O2—C4—C5	104.3 (8)	H16A—C16—H16B	108.2
C3—C4—H4	109.3	C20—O6—H6	109.5
C3—C4—C5	115.5 (11)	C24—O7—H7	109.5
C5—C4—H4	109.3	O5—C20—O6	121.6 (12)
N2—C5—C4	100.2 (9)	O5—C20—C21	122.5 (12)
N2—C5—H5A	111.7	O6—C20—C21	115.9 (10)
N2—C5—H5B	111.7	C22—C21—C20	122.5 (11)
C4—C5—H5A	111.7	C26—C21—C20	121.6 (11)
C4—C5—H5B	111.7	C26—C21—C22	115.9 (11)
H5A—C5—H5B	109.5	C21—C22—H22	119.6
O2—C6—N2	110.3 (9)	C23—C22—C21	120.8 (12)
O3—C6—O2	123.1 (9)	C23—C22—H22	119.6
O3—C6—N2	126.6 (10)	C22—C23—H23	118.9
N2—C7—C8	122.7 (10)	C22—C23—C24	122.1 (12)
N2—C7—C12	119.7 (9)	C24—C23—H23	118.9
C12—C7—C8	117.6 (11)	O7—C24—C23	124.2 (12)
C7—C8—H8	120.8	O7—C24—C25	118.1 (12)
C9—C8—C7	118.4 (11)	C23—C24—C25	117.6 (13)
C9—C8—H8	120.8	C24—C25—H25	119.7
F1—C9—C10	115.2 (11)	C26—C25—C24	120.7 (14)
C8—C9—F1	118.1 (11)	C26—C25—H25	119.7
C8—C9—C10	126.7 (10)	C21—C26—H26	118.6
N1—C10—C9	120.5 (10)	C25—C26—C21	122.7 (13)
C11—C10—N1	125.9 (12)	C25—C26—H26	118.6
C11—C10—C9	113.6 (11)	H1WA—O1W—H1WB	104.4
C10—C11—H11	118.7

F1—C9—C10—N1	−3 (2)	C8—C7—C12—C11	−3 (2)
F1—C9—C10—C11	177.1 (13)	C8—C9—C10—N1	179.8 (15)
O2—C4—C5—N2	−24.9 (13)	C8—C9—C10—C11	0 (2)
O4—C15—C16—N1	−57 (2)	C9—C10—C11—C12	−2 (2)
N1—C10—C11—C12	178.4 (16)	C10—N1—C13—C14	175.5 (14)
N1—C13—C14—O4	56 (2)	C10—N1—C16—C15	−176.3 (17)
N2—C7—C8—C9	180.0 (13)	C10—C11—C12—C7	3 (2)
N2—C7—C12—C11	178.2 (14)	C12—C7—C8—C9	1.0 (19)
N3—C3—C4—O2	−172.9 (9)	C13—N1—C10—C9	−65.7 (19)
N3—C3—C4—C5	70.3 (12)	C13—N1—C10—C11	114.2 (18)
C2—N3—C3—C4	84.9 (13)	C13—N1—C16—C15	56.8 (19)
C3—N3—C2—O1	−9.4 (18)	C14—O4—C15—C16	53 (2)
C3—N3—C2—C1	173.4 (12)	C15—O4—C14—C13	−52 (2)
C3—C4—C5—N2	94.4 (12)	C16—N1—C10—C9	170.8 (15)
C4—O2—C6—O3	172.6 (14)	C16—N1—C10—C11	−9 (2)
C4—O2—C6—N2	−4.2 (15)	C16—N1—C13—C14	−58.5 (19)
C5—N2—C6—O2	−13.3 (15)	O5—C20—C21—C22	178.8 (14)
C5—N2—C6—O3	170.0 (14)	O5—C20—C21—C26	0 (2)
C5—N2—C7—C8	179.2 (12)	O6—C20—C21—C22	−1 (2)
C5—N2—C7—C12	−2 (2)	O6—C20—C21—C26	179.9 (14)
C6—O2—C4—C3	−104.8 (10)	O7—C24—C25—C26	179.9 (14)
C6—O2—C4—C5	19.1 (14)	C20—C21—C22—C23	178.2 (14)
C6—N2—C5—C4	23.3 (14)	C20—C21—C26—C25	−178.5 (14)
C6—N2—C7—C8	−20 (2)	C21—C22—C23—C24	2 (2)
C6—N2—C7—C12	158.8 (14)	C22—C21—C26—C25	3 (2)
C7—N2—C5—C4	−173.0 (12)	C22—C23—C24—O7	179.7 (15)
C7—N2—C6—O2	−176.4 (12)	C22—C23—C24—C25	0 (2)
C7—N2—C6—O3	7 (2)	C23—C24—C25—C26	0 (2)
C7—C8—C9—F1	−176.7 (13)	C24—C25—C26—C21	−1 (2)
C7—C8—C9—C10	0 (2)	C26—C21—C22—C23	−3 (2)

(LIN:2,6-DHBA) top

Crystal data top

C₁₆H₂₀FN₃O₄·C₇H₆O₄	D_x = 1.456 Mg m⁻³
M_r = 491.47	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 11050 reflections
a = 4.7535 (3) Å	θ = 3.0–74.7°
b = 15.8010 (6) Å	µ = 0.99 mm⁻¹
c = 29.8550 (11) Å	T = 293 K
V = 2242.42 (17) Å³	Needle
Z = 4	0.47 × 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 Source	3744 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.087
Detector resolution: 4.1685 pixels mm^-1	θ_max = 77.5°, θ_min = 3.0°
ω scans	h = −5→5
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 = −19→19
T_min = 0.269, T_max = 1.000	l = −37→37
29271 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0746P)²] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.042	(Δ/σ)_max < 0.001
wR(F²) = 0.122	Δρ_max = 0.17 e Å⁻³
S = 1.02	Δρ_min = −0.14 e Å⁻³
4581 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
321 parameters	Extinction coefficient: 0.0018 (5)
0 restraints	Absolute 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 methods	Absolute structure parameter: −0.13 (11)
Hydrogen site location: inferred from neighbouring sites

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.3959 (5)	0.58263 (12)	0.26302 (6)	0.0762 (6)
O1	1.2809 (6)	1.00463 (15)	0.43806 (8)	0.0752 (7)
O2	0.9674 (6)	0.74121 (12)	0.45850 (6)	0.0683 (7)
O3	1.1623 (7)	0.61554 (13)	0.44513 (7)	0.0772 (8)
O4	0.8180 (7)	0.33357 (15)	0.17837 (7)	0.0772 (7)
N1	0.7230 (6)	0.43711 (13)	0.25544 (7)	0.0550 (6)
N2	0.8263 (6)	0.67239 (12)	0.39801 (7)	0.0519 (6)
N3	0.9601 (6)	0.92428 (13)	0.47189 (7)	0.0566 (6)
H3	0.878884	0.909901	0.496482	0.068*
C1	1.2057 (9)	1.02874 (19)	0.51626 (11)	0.0704 (9)
H1A	1.393913	1.016855	0.526058	0.106*
H1B	1.074309	1.008756	0.538279	0.106*
H1C	1.183102	1.088678	0.512433	0.106*
C2	1.1520 (8)	0.98486 (15)	0.47252 (9)	0.0555 (7)
C3	0.8834 (8)	0.88146 (16)	0.43060 (8)	0.0592 (8)
H3A	1.049573	0.875267	0.412039	0.071*
H3B	0.749177	0.916030	0.414348	0.071*
C4	0.7580 (7)	0.79615 (15)	0.43879 (8)	0.0534 (7)
H4	0.594669	0.800948	0.458670	0.064*
C5	0.6746 (8)	0.75191 (15)	0.39522 (8)	0.0559 (7)
H5A	0.473103	0.742630	0.393785	0.067*
H5B	0.733138	0.784440	0.369287	0.067*
C6	0.9958 (8)	0.66986 (15)	0.43393 (8)	0.0570 (7)
C7	0.8057 (7)	0.61067 (14)	0.36350 (8)	0.0514 (7)
C8	0.6162 (8)	0.62442 (16)	0.32886 (8)	0.0556 (7)
H8	0.504189	0.672675	0.328949	0.067*
C9	0.5935 (8)	0.56715 (16)	0.29452 (8)	0.0555 (7)
C10	0.7559 (7)	0.49425 (15)	0.29141 (8)	0.0519 (7)
C11	0.9406 (8)	0.48146 (16)	0.32701 (9)	0.0602 (8)
H11	1.052720	0.433218	0.326879	0.072*
C12	0.9651 (8)	0.53725 (17)	0.36256 (9)	0.0586 (8)
H12	1.088727	0.525413	0.385871	0.070*
C13	0.7605 (9)	0.47355 (18)	0.21052 (9)	0.0646 (9)
H13A	0.957389	0.486856	0.205681	0.077*
H13B	0.653169	0.525551	0.208031	0.077*
C14	0.6626 (11)	0.4114 (2)	0.17579 (10)	0.0780 (11)
H14A	0.464068	0.399838	0.180163	0.094*
H14B	0.685914	0.435903	0.146229	0.094*
C15	0.7910 (10)	0.29863 (19)	0.22206 (10)	0.0722 (10)
H15A	0.902524	0.247339	0.223918	0.087*
H15B	0.595951	0.283434	0.227208	0.087*
C16	0.8850 (9)	0.35918 (16)	0.25810 (9)	0.0614 (8)
H16A	0.858878	0.333406	0.287288	0.074*
H16B	1.083477	0.371675	0.254415	0.074*
O5	0.3549 (6)	0.62421 (13)	0.06430 (8)	0.0715 (6)
H5	0.468139	0.585073	0.064868	0.107*
O6	0.2920 (7)	0.58413 (14)	0.13501 (8)	0.0812 (8)
O7	−0.0483 (8)	0.66707 (17)	0.18534 (9)	0.0884 (9)
H7	0.034475	0.623854	0.177762	0.133*
O8	0.0905 (7)	0.75505 (16)	0.03169 (8)	0.0776 (7)
H8A	0.210697	0.717820	0.031455	0.116*
C20	0.2356 (8)	0.63204 (17)	0.10411 (10)	0.0613 (8)
C21	0.0287 (7)	0.70131 (16)	0.10766 (10)	0.0573 (7)
C22	−0.1116 (9)	0.71315 (18)	0.14875 (11)	0.0666 (8)
C23	−0.3177 (9)	0.7751 (2)	0.15314 (14)	0.0770 (10)
H23	−0.413449	0.781710	0.180078	0.092*
C24	−0.3780 (9)	0.8261 (2)	0.11741 (15)	0.0810 (11)
H24	−0.516787	0.867225	0.120426	0.097*
C25	−0.2401 (9)	0.8186 (2)	0.07727 (13)	0.0745 (10)
H25	−0.283542	0.854616	0.053643	0.089*
C26	−0.0356 (8)	0.75690 (18)	0.07211 (11)	0.0622 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0872 (15)	0.0792 (10)	0.0623 (9)	0.0194 (11)	−0.0285 (10)	−0.0174 (8)
O1	0.0851 (19)	0.0728 (12)	0.0676 (12)	−0.0237 (13)	0.0157 (12)	−0.0054 (9)
O2	0.102 (2)	0.0509 (9)	0.0524 (9)	0.0055 (11)	−0.0212 (11)	−0.0076 (7)
O3	0.110 (2)	0.0604 (10)	0.0616 (11)	0.0151 (13)	−0.0346 (13)	−0.0049 (8)
O4	0.098 (2)	0.0760 (12)	0.0581 (11)	0.0133 (14)	0.0017 (12)	−0.0174 (9)
N1	0.0720 (19)	0.0479 (9)	0.0451 (10)	−0.0006 (11)	−0.0015 (10)	−0.0044 (7)
N2	0.0662 (17)	0.0455 (9)	0.0440 (9)	0.0010 (11)	−0.0076 (10)	−0.0026 (7)
N3	0.0733 (19)	0.0495 (10)	0.0472 (10)	−0.0111 (11)	0.0115 (11)	−0.0059 (8)
C1	0.081 (3)	0.0609 (14)	0.0689 (16)	−0.0030 (17)	−0.0031 (17)	−0.0169 (12)
C2	0.063 (2)	0.0463 (11)	0.0574 (13)	0.0014 (12)	0.0022 (13)	−0.0039 (9)
C3	0.082 (2)	0.0513 (12)	0.0442 (11)	−0.0077 (14)	0.0052 (13)	−0.0038 (9)
C4	0.066 (2)	0.0492 (11)	0.0450 (11)	−0.0013 (12)	0.0033 (12)	−0.0031 (9)
C5	0.071 (2)	0.0474 (10)	0.0497 (11)	0.0034 (13)	−0.0045 (13)	−0.0039 (9)
C6	0.080 (2)	0.0461 (11)	0.0452 (11)	−0.0032 (13)	−0.0119 (13)	0.0014 (8)
C7	0.062 (2)	0.0470 (10)	0.0449 (11)	−0.0014 (12)	−0.0032 (12)	−0.0022 (8)
C8	0.067 (2)	0.0491 (11)	0.0503 (12)	0.0057 (13)	−0.0083 (12)	−0.0035 (9)
C9	0.063 (2)	0.0563 (12)	0.0467 (11)	0.0039 (13)	−0.0114 (12)	−0.0030 (10)
C10	0.063 (2)	0.0466 (10)	0.0457 (11)	−0.0027 (12)	−0.0006 (11)	−0.0014 (9)
C11	0.076 (2)	0.0486 (11)	0.0562 (13)	0.0078 (13)	−0.0074 (13)	−0.0027 (9)
C12	0.072 (2)	0.0522 (12)	0.0518 (12)	0.0058 (14)	−0.0133 (13)	−0.0026 (9)
C13	0.086 (3)	0.0599 (13)	0.0483 (12)	0.0032 (16)	0.0035 (14)	0.0007 (10)
C14	0.099 (3)	0.086 (2)	0.0485 (13)	0.018 (2)	−0.0012 (16)	−0.0153 (13)
C15	0.092 (3)	0.0578 (14)	0.0666 (16)	−0.0030 (17)	0.0035 (17)	−0.0153 (12)
C16	0.079 (2)	0.0496 (12)	0.0555 (13)	0.0009 (14)	−0.0010 (14)	−0.0039 (10)
O5	0.0748 (18)	0.0631 (11)	0.0765 (13)	0.0149 (12)	0.0071 (12)	0.0011 (9)
O6	0.099 (2)	0.0643 (11)	0.0805 (14)	0.0138 (14)	0.0016 (14)	0.0126 (10)
O7	0.110 (3)	0.0785 (14)	0.0764 (13)	0.0013 (16)	0.0176 (15)	0.0096 (11)
O8	0.0807 (19)	0.0819 (14)	0.0702 (12)	0.0147 (14)	−0.0001 (12)	0.0086 (10)
C20	0.066 (2)	0.0501 (11)	0.0680 (15)	−0.0026 (14)	−0.0017 (14)	−0.0011 (10)
C21	0.054 (2)	0.0471 (12)	0.0708 (15)	−0.0045 (12)	−0.0021 (14)	−0.0063 (10)
C22	0.070 (2)	0.0565 (13)	0.0729 (16)	−0.0092 (16)	0.0022 (16)	−0.0063 (12)
C23	0.061 (2)	0.0770 (18)	0.093 (2)	−0.0066 (18)	0.0116 (19)	−0.0241 (17)
C24	0.060 (2)	0.0690 (17)	0.114 (3)	0.0095 (18)	−0.008 (2)	−0.0254 (18)
C25	0.066 (3)	0.0620 (15)	0.095 (2)	0.0118 (17)	−0.0149 (19)	−0.0051 (15)
C26	0.060 (2)	0.0556 (13)	0.0712 (16)	0.0007 (14)	−0.0074 (15)	−0.0050 (11)

Geometric parameters (Å, º) top

F1—C9	1.352 (4)	C7—C12	1.386 (4)
O1—C2	1.238 (4)	C8—C9	1.372 (3)
O2—C4	1.446 (4)	C9—C10	1.390 (4)
O2—C6	1.352 (3)	C10—C11	1.393 (4)
O3—C6	1.214 (4)	C11—C12	1.385 (4)
O4—C14	1.437 (4)	C13—C14	1.502 (4)
O4—C15	1.422 (4)	C15—C16	1.508 (4)
N1—C10	1.412 (3)	O5—C20	1.323 (4)
N1—C13	1.470 (3)	O6—C20	1.223 (4)
N1—C16	1.455 (4)	O7—C22	1.347 (4)
N2—C5	1.451 (3)	O8—C26	1.348 (4)
N2—C6	1.342 (4)	C20—C21	1.475 (4)
N2—C7	1.422 (3)	C21—C22	1.409 (5)
N3—C2	1.322 (4)	C21—C26	1.411 (4)
N3—C3	1.453 (3)	C22—C23	1.391 (5)
C1—C2	1.500 (4)	C23—C24	1.368 (6)
C3—C4	1.494 (4)	C24—C25	1.371 (6)
C4—C5	1.529 (3)	C25—C26	1.385 (5)
C7—C8	1.389 (4)

C6—O2—C4	110.4 (2)	C8—C9—C10	123.6 (3)
C15—O4—C14	109.6 (2)	C9—C10—N1	121.3 (2)
C10—N1—C13	115.5 (2)	C9—C10—C11	114.8 (2)
C10—N1—C16	116.2 (2)	C11—C10—N1	123.9 (2)
C16—N1—C13	108.5 (2)	C12—C11—C10	123.0 (3)
C6—N2—C5	111.7 (2)	C11—C12—C7	120.2 (3)
C6—N2—C7	126.9 (2)	N1—C13—C14	109.6 (3)
C7—N2—C5	121.2 (2)	O4—C14—C13	111.3 (3)
C2—N3—C3	121.5 (2)	O4—C15—C16	112.4 (3)
O1—C2—N3	120.8 (2)	N1—C16—C15	110.0 (3)
O1—C2—C1	121.5 (3)	O5—C20—C21	114.8 (3)
N3—C2—C1	117.7 (3)	O6—C20—O5	121.7 (3)
N3—C3—C4	112.4 (2)	O6—C20—C21	123.5 (3)
O2—C4—C3	109.5 (3)	C22—C21—C20	118.5 (3)
O2—C4—C5	104.5 (2)	C22—C21—C26	118.0 (3)
C3—C4—C5	112.1 (2)	C26—C21—C20	123.5 (3)
N2—C5—C4	102.6 (2)	O7—C22—C21	121.9 (3)
O3—C6—O2	120.3 (2)	O7—C22—C23	117.5 (3)
O3—C6—N2	129.2 (2)	C23—C22—C21	120.6 (3)
N2—C6—O2	110.4 (2)	C24—C23—C22	119.3 (3)
C8—C7—N2	118.5 (2)	C23—C24—C25	122.0 (4)
C12—C7—N2	123.5 (3)	C24—C25—C26	119.6 (3)
C12—C7—C8	118.1 (2)	O8—C26—C21	124.3 (3)
C9—C8—C7	120.3 (3)	O8—C26—C25	115.3 (3)
F1—C9—C8	117.1 (3)	C25—C26—C21	120.4 (3)
F1—C9—C10	119.3 (2)

(LIN:3,4-DHBA:H2O) top

Crystal data top

2(C₁₆H₂₀FN₃O₄)·2(C₇H₆O₄)·1.25(H₂O)	D_x = 1.411 Mg m⁻³
M_r = 1005.45	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2	Cell parameters from 38569 reflections
a = 30.3989 (2) Å	θ = 2.9–75.1°
b = 16.10240 (15) Å	µ = 0.97 mm⁻¹
c = 9.66944 (7) Å	T = 293 K
V = 4733.14 (7) Å³	Plate
Z = 4	0.33 × 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 Source	9333 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 4.1685 pixels mm^-1	θ_max = 75.3°, θ_min = 2.9°
ω scans	h = −38→38
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 = −20→16
T_min = 0.790, T_max = 1.000	l = −12→12
61242 measured reflections

Refinement top

Refinement on F²	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.1003P)² + 0.451P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.044	(Δ/σ)_max < 0.001
wR(F²) = 0.134	Δρ_max = 0.47 e Å⁻³
S = 1.02	Δρ_min = −0.32 e Å⁻³
9687 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
684 parameters	Extinction coefficient: 0.00034 (10)
0 restraints	Absolute 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 methods	Absolute structure parameter: 0.05 (3)
Hydrogen site location: mixed

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1A	0.52546 (6)	0.18385 (15)	0.04172 (18)	0.0711 (5)
O1A	0.22670 (7)	0.15918 (15)	0.64836 (19)	0.0599 (5)
O2A	0.32240 (6)	0.16722 (14)	0.2566 (2)	0.0567 (4)
O3A	0.36986 (7)	0.1716 (2)	0.0805 (2)	0.0761 (7)
O4A	0.66581 (6)	0.06542 (14)	0.2581 (2)	0.0613 (5)
N1A	0.57873 (6)	0.13089 (14)	0.2523 (2)	0.0494 (4)
N2A	0.39343 (7)	0.15531 (15)	0.3071 (2)	0.0488 (5)
N3A	0.24620 (7)	0.12997 (16)	0.4287 (2)	0.0506 (5)
H3A	0.238128	0.129442	0.343507	0.061*
C1A	0.17052 (9)	0.1636 (2)	0.4761 (3)	0.0615 (7)
H1AA	0.150909	0.132985	0.534941	0.092*
H1AB	0.167789	0.143879	0.382823	0.092*
H1AC	0.163148	0.221517	0.479551	0.092*
C2A	0.21681 (8)	0.15170 (16)	0.5245 (3)	0.0455 (5)
C3A	0.29116 (8)	0.10719 (19)	0.4618 (3)	0.0522 (6)
H3AA	0.297153	0.052412	0.424555	0.063*
H3AB	0.294343	0.104234	0.561471	0.063*
C4A	0.32434 (8)	0.16724 (17)	0.4055 (3)	0.0488 (5)
H4A	0.318278	0.223151	0.440702	0.059*
C5A	0.37172 (8)	0.1429 (2)	0.4389 (3)	0.0529 (6)
H5AA	0.384113	0.178405	0.509896	0.063*
H5AB	0.373648	0.085443	0.468540	0.063*
C6A	0.36350 (9)	0.1655 (2)	0.2026 (3)	0.0537 (6)
C7A	0.43952 (8)	0.14859 (16)	0.2913 (3)	0.0458 (5)
C8A	0.46046 (8)	0.16710 (19)	0.1675 (3)	0.0509 (6)
H8A	0.444356	0.183454	0.090366	0.061*
C9A	0.50567 (8)	0.16070 (18)	0.1613 (3)	0.0494 (5)
C10A	0.53229 (8)	0.13505 (16)	0.2699 (3)	0.0473 (5)
C11A	0.51019 (8)	0.1165 (2)	0.3922 (3)	0.0567 (6)
H11A	0.526292	0.098668	0.468472	0.068*
C12A	0.46491 (8)	0.1237 (2)	0.4036 (3)	0.0565 (7)
H12A	0.451314	0.111794	0.487488	0.068*
C13A	0.59295 (9)	0.0661 (2)	0.1542 (3)	0.0567 (6)
H13C	0.577635	0.073081	0.067026	0.068*
H13D	0.585589	0.011730	0.190850	0.068*
C14A	0.64219 (9)	0.0716 (2)	0.1306 (3)	0.0582 (6)
H14C	0.651353	0.027275	0.069205	0.070*
H14D	0.649113	0.124106	0.086422	0.070*
C15A	0.65238 (9)	0.1305 (3)	0.3493 (4)	0.0674 (8)
H15C	0.658628	0.183858	0.307062	0.081*
H15D	0.668970	0.126902	0.434778	0.081*
C16A	0.60371 (9)	0.1244 (2)	0.3807 (3)	0.0618 (7)
H16C	0.597424	0.071804	0.425376	0.074*
H16D	0.595191	0.168739	0.443195	0.074*
O5A	0.90944 (6)	0.28778 (12)	0.2511 (2)	0.0579 (4)
O6A	0.94463 (6)	0.16856 (14)	0.2154 (3)	0.0612 (5)
H6A	0.965719	0.195842	0.242422	0.16 (3)*
O7A	0.74718 (6)	0.19199 (13)	0.2431 (3)	0.0681 (6)
H7A	0.748067	0.238065	0.279165	0.102*
O8A	0.75294 (6)	0.02642 (12)	0.2270 (3)	0.0605 (5)
H8AA	0.731620	0.056022	0.243335	0.091*
C20A	0.90922 (8)	0.21048 (16)	0.2325 (3)	0.0456 (5)
C21A	0.86761 (7)	0.16369 (16)	0.2311 (2)	0.0439 (5)
C22A	0.82697 (8)	0.20518 (15)	0.2388 (3)	0.0473 (5)
H22A	0.826011	0.262826	0.243964	0.057*
C23A	0.78837 (8)	0.15939 (16)	0.2385 (3)	0.0481 (5)
C24A	0.78979 (8)	0.07272 (16)	0.2289 (3)	0.0471 (5)
C25A	0.83038 (8)	0.03211 (16)	0.2222 (3)	0.0501 (5)
H25A	0.831434	−0.025513	0.216719	0.060*
C26A	0.86883 (8)	0.07738 (16)	0.2239 (3)	0.0475 (5)
H26A	0.895771	0.050113	0.220132	0.057*
F1B	0.59101 (6)	0.65823 (19)	0.48400 (18)	0.0827 (7)
O1B	0.29761 (7)	0.67170 (13)	−0.14862 (18)	0.0544 (4)
O2B	0.3926 (4)	0.623 (2)	0.2556 (15)	0.086 (5)	0.63 (5)
O3B	0.4382 (3)	0.640 (3)	0.4306 (9)	0.120 (8)	0.63 (5)
C6B	0.4305 (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)
O4B	0.73722 (6)	0.57266 (13)	0.2591 (3)	0.0609 (5)
N1B	0.64850 (6)	0.62900 (14)	0.2669 (2)	0.0472 (4)
N2B	0.46315 (7)	0.61833 (18)	0.2033 (2)	0.0552 (6)
N3B	0.31985 (7)	0.65756 (17)	0.0715 (2)	0.0545 (5)
H3B	0.312207	0.649903	0.156180	0.065*
C1B	0.24365 (9)	0.6315 (2)	0.0185 (3)	0.0603 (7)
H1BA	0.223541	0.675758	−0.001977	0.090*
H1BB	0.243568	0.620857	0.116183	0.090*
H1BC	0.234758	0.582239	−0.030043	0.090*
C2B	0.28891 (8)	0.65565 (17)	−0.0262 (2)	0.0461 (5)
C3B	0.36590 (8)	0.6721 (2)	0.0405 (3)	0.0571 (6)
H3BA	0.374592	0.725726	0.077009	0.068*
H3BB	0.369984	0.673200	−0.058928	0.068*
C4B	0.39428 (8)	0.60655 (19)	0.1012 (3)	0.0532 (6)
H4B	0.383347	0.550894	0.078877	0.064*	0.63 (5)
H4BA	0.384862	0.554417	0.058131	0.064*	0.37 (5)
C5B	0.44318 (8)	0.6152 (2)	0.0674 (3)	0.0538 (6)
H5BA	0.453754	0.567870	0.014981	0.065*
H5BB	0.448958	0.665638	0.015680	0.065*
C7B	0.50926 (8)	0.62137 (18)	0.2218 (3)	0.0491 (5)
C8B	0.52868 (9)	0.6368 (2)	0.3500 (3)	0.0585 (7)
H8B	0.511423	0.645245	0.428106	0.070*
C9B	0.57342 (9)	0.6393 (2)	0.3586 (3)	0.0549 (7)
C10B	0.60233 (7)	0.62554 (15)	0.2486 (3)	0.0442 (5)
C11B	0.58164 (8)	0.61327 (19)	0.1220 (3)	0.0476 (5)
H11B	0.598949	0.605631	0.043760	0.057*
C12B	0.53645 (8)	0.61196 (19)	0.1078 (3)	0.0497 (5)
H12B	0.524107	0.604668	0.020613	0.060*
C13B	0.66577 (9)	0.5680 (2)	0.3673 (3)	0.0571 (6)
H13A	0.660139	0.512196	0.333923	0.069*
H13B	0.650765	0.574675	0.455115	0.069*
C14B	0.71453 (9)	0.5800 (2)	0.3875 (3)	0.0588 (7)
H14A	0.719973	0.634405	0.426848	0.071*
H14B	0.725527	0.538604	0.451670	0.071*
C15B	0.72206 (8)	0.6361 (2)	0.1672 (3)	0.0592 (7)
H15A	0.738449	0.633418	0.081184	0.071*
H15B	0.727039	0.690181	0.208355	0.071*
C16B	0.67361 (8)	0.6249 (2)	0.1381 (3)	0.0533 (6)
H16A	0.663630	0.667980	0.075430	0.064*
H16B	0.668764	0.571542	0.093928	0.064*
O5B	0.97971 (6)	0.75612 (11)	0.2442 (3)	0.0581 (5)
O6B	1.01418 (6)	0.63447 (12)	0.2482 (3)	0.0614 (5)
H6B	1.035563	0.664885	0.237769	0.107 (17)*
O7B	0.81741 (6)	0.67448 (12)	0.2447 (3)	0.0677 (6)
H7B	0.819838	0.721974	0.215107	0.101*
O8B	0.81834 (6)	0.50739 (12)	0.2453 (3)	0.0635 (5)
H8BA	0.797659	0.540087	0.246173	0.095*
C20B	0.97904 (7)	0.67803 (15)	0.2465 (3)	0.0463 (5)
C21B	0.93658 (7)	0.63363 (15)	0.2462 (3)	0.0448 (5)
C22B	0.89715 (7)	0.67839 (15)	0.2457 (3)	0.0453 (5)
H22B	0.897734	0.736128	0.246482	0.054*
C23B	0.85731 (7)	0.63702 (15)	0.2442 (3)	0.0456 (5)
C24B	0.85639 (8)	0.54984 (15)	0.2449 (3)	0.0476 (5)
C25B	0.89551 (8)	0.50601 (16)	0.2444 (4)	0.0564 (6)
H25B	0.894976	0.448263	0.243740	0.068*
C26B	0.93557 (8)	0.54741 (16)	0.2448 (3)	0.0539 (6)
H26B	0.961713	0.517417	0.244224	0.065*
O2W	0.92434 (17)	0.9013 (3)	0.2829 (5)	0.1366 (16)
H2WA	0.946379	0.933836	0.283604	0.205*
H2WB	0.936059	0.854016	0.269714	0.205*
O1W	1.000000	1.000000	0.1976 (14)	0.136 (4)	0.5
H1WA	1.013680	0.966900	0.250862	0.205*	0.25
H1WB	0.986220	1.033100	0.250862	0.205*	0.25

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0550 (9)	0.1109 (15)	0.0474 (8)	0.0095 (9)	0.0108 (7)	0.0230 (9)
O1A	0.0632 (11)	0.0760 (13)	0.0406 (9)	0.0014 (10)	0.0018 (8)	−0.0084 (9)
O2A	0.0380 (8)	0.0830 (12)	0.0492 (9)	−0.0015 (8)	−0.0051 (7)	0.0045 (10)
O3A	0.0509 (10)	0.136 (2)	0.0419 (10)	0.0018 (13)	−0.0055 (8)	0.0111 (12)
O4A	0.0432 (9)	0.0757 (12)	0.0649 (12)	0.0061 (8)	0.0001 (9)	0.0017 (11)
N1A	0.0398 (9)	0.0615 (11)	0.0468 (10)	0.0018 (8)	0.0012 (8)	−0.0027 (10)
N2A	0.0383 (10)	0.0675 (13)	0.0406 (10)	−0.0001 (9)	−0.0022 (8)	0.0013 (9)
N3A	0.0399 (10)	0.0708 (14)	0.0412 (10)	−0.0021 (9)	0.0023 (8)	−0.0031 (9)
C1A	0.0457 (13)	0.087 (2)	0.0517 (14)	0.0056 (14)	0.0046 (11)	−0.0022 (14)
C2A	0.0463 (12)	0.0493 (13)	0.0409 (11)	−0.0027 (10)	0.0049 (9)	−0.0013 (9)
C3A	0.0409 (11)	0.0620 (15)	0.0538 (13)	0.0013 (11)	0.0019 (10)	0.0020 (12)
C4A	0.0412 (11)	0.0582 (13)	0.0469 (12)	−0.0015 (10)	−0.0015 (9)	−0.0027 (11)
C5A	0.0375 (11)	0.0788 (18)	0.0424 (12)	−0.0005 (11)	−0.0004 (9)	−0.0003 (11)
C6A	0.0422 (12)	0.0746 (17)	0.0441 (12)	−0.0005 (12)	−0.0055 (9)	0.0026 (12)
C7A	0.0392 (11)	0.0556 (13)	0.0426 (11)	−0.0004 (9)	−0.0021 (9)	0.0004 (10)
C8A	0.0446 (12)	0.0648 (15)	0.0434 (12)	0.0028 (11)	−0.0025 (10)	0.0058 (11)
C9A	0.0465 (12)	0.0608 (14)	0.0409 (11)	0.0012 (11)	0.0054 (10)	0.0061 (11)
C10A	0.0399 (11)	0.0575 (12)	0.0446 (12)	0.0015 (9)	0.0004 (10)	0.0000 (11)
C11A	0.0419 (12)	0.0859 (19)	0.0424 (12)	0.0006 (12)	−0.0025 (9)	0.0065 (13)
C12A	0.0407 (12)	0.089 (2)	0.0396 (11)	−0.0005 (12)	−0.0007 (10)	0.0079 (13)
C13A	0.0477 (13)	0.0646 (16)	0.0579 (15)	0.0044 (12)	−0.0022 (11)	−0.0085 (13)
C14A	0.0503 (13)	0.0688 (17)	0.0555 (14)	0.0077 (12)	0.0041 (11)	−0.0012 (13)
C15A	0.0400 (13)	0.099 (2)	0.0631 (17)	0.0002 (14)	−0.0001 (12)	−0.0105 (17)
C16A	0.0417 (12)	0.095 (2)	0.0487 (13)	0.0019 (13)	0.0005 (10)	−0.0033 (14)
O5A	0.0490 (9)	0.0529 (9)	0.0719 (12)	−0.0047 (7)	0.0035 (9)	−0.0063 (10)
O6A	0.0402 (8)	0.0648 (11)	0.0786 (14)	−0.0003 (8)	0.0088 (9)	−0.0155 (10)
O7A	0.0383 (8)	0.0575 (10)	0.1084 (18)	0.0025 (7)	0.0030 (11)	−0.0078 (13)
O8A	0.0420 (8)	0.0548 (10)	0.0848 (14)	−0.0052 (7)	0.0047 (9)	−0.0008 (10)
C20A	0.0417 (11)	0.0539 (12)	0.0413 (10)	0.0000 (9)	0.0022 (9)	−0.0030 (10)
C21A	0.0394 (10)	0.0526 (12)	0.0396 (10)	−0.0017 (9)	0.0014 (9)	−0.0015 (10)
C22A	0.0427 (11)	0.0474 (11)	0.0519 (12)	0.0010 (9)	0.0011 (10)	−0.0035 (11)
C23A	0.0399 (10)	0.0531 (12)	0.0512 (12)	0.0025 (9)	0.0008 (10)	−0.0007 (11)
C24A	0.0420 (11)	0.0511 (12)	0.0483 (12)	−0.0024 (9)	0.0022 (10)	0.0019 (10)
C25A	0.0472 (12)	0.0471 (12)	0.0561 (14)	−0.0001 (10)	0.0028 (10)	0.0023 (10)
C26A	0.0412 (11)	0.0533 (12)	0.0479 (12)	0.0043 (9)	0.0017 (10)	0.0010 (10)
F1B	0.0533 (9)	0.154 (2)	0.0411 (8)	0.0033 (11)	−0.0074 (7)	−0.0201 (11)
O1B	0.0602 (10)	0.0617 (11)	0.0412 (8)	−0.0030 (9)	0.0015 (8)	0.0040 (8)
O2B	0.037 (2)	0.177 (13)	0.045 (3)	0.002 (6)	0.0042 (19)	0.014 (7)
O3B	0.047 (3)	0.27 (3)	0.048 (2)	0.017 (7)	0.0075 (18)	0.010 (7)
C6B	0.037 (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)
O4B	0.0392 (8)	0.0661 (11)	0.0774 (13)	0.0070 (8)	−0.0009 (9)	0.0061 (11)
N1B	0.0361 (9)	0.0603 (11)	0.0451 (10)	0.0016 (8)	−0.0019 (8)	0.0039 (9)
N2B	0.0334 (10)	0.0857 (16)	0.0464 (11)	0.0004 (10)	0.0039 (8)	0.0089 (11)
N3B	0.0378 (10)	0.0822 (16)	0.0433 (10)	0.0048 (10)	0.0019 (8)	0.0106 (10)
C1B	0.0445 (13)	0.087 (2)	0.0499 (14)	−0.0023 (13)	−0.0022 (10)	−0.0003 (14)
C2B	0.0436 (11)	0.0530 (13)	0.0417 (11)	0.0066 (10)	0.0000 (9)	−0.0006 (10)
C3B	0.0408 (12)	0.0687 (17)	0.0616 (15)	0.0027 (12)	0.0026 (11)	0.0164 (13)
C4B	0.0362 (11)	0.0610 (15)	0.0624 (15)	−0.0024 (10)	−0.0001 (10)	0.0103 (12)
C5B	0.0351 (11)	0.0763 (17)	0.0501 (13)	−0.0016 (12)	−0.0003 (9)	0.0060 (13)
C7B	0.0367 (11)	0.0667 (15)	0.0440 (12)	0.0026 (10)	0.0026 (9)	0.0044 (11)
C8B	0.0432 (12)	0.091 (2)	0.0416 (12)	0.0030 (13)	0.0031 (10)	0.0000 (13)
C9B	0.0454 (12)	0.0836 (19)	0.0357 (11)	0.0033 (12)	−0.0024 (10)	−0.0046 (11)
C10B	0.0363 (10)	0.0552 (12)	0.0411 (11)	0.0006 (9)	−0.0008 (9)	0.0006 (10)
C11B	0.0384 (11)	0.0656 (15)	0.0388 (11)	0.0017 (10)	0.0027 (9)	−0.0005 (10)
C12B	0.0373 (11)	0.0708 (15)	0.0409 (11)	0.0017 (11)	−0.0012 (9)	0.0019 (11)
C13B	0.0433 (12)	0.0690 (16)	0.0591 (15)	−0.0016 (12)	−0.0062 (11)	0.0140 (13)
C14B	0.0444 (13)	0.0709 (17)	0.0611 (16)	0.0032 (12)	−0.0101 (11)	0.0065 (13)
C15B	0.0363 (11)	0.0768 (18)	0.0646 (16)	0.0008 (11)	0.0008 (11)	0.0107 (14)
C16B	0.0374 (11)	0.0746 (17)	0.0479 (13)	0.0011 (11)	0.0007 (10)	0.0022 (12)
O5B	0.0430 (8)	0.0501 (9)	0.0811 (13)	−0.0010 (7)	0.0015 (10)	−0.0046 (10)
O6B	0.0365 (8)	0.0593 (10)	0.0883 (14)	0.0030 (8)	−0.0047 (10)	0.0112 (11)
O7B	0.0382 (8)	0.0488 (9)	0.1160 (18)	0.0034 (7)	−0.0034 (11)	0.0071 (12)
O8B	0.0398 (8)	0.0493 (9)	0.1013 (16)	−0.0030 (7)	0.0029 (10)	0.0041 (11)
C20B	0.0390 (10)	0.0516 (12)	0.0483 (12)	0.0020 (9)	−0.0021 (10)	0.0035 (11)
C21B	0.0405 (11)	0.0491 (11)	0.0448 (11)	0.0010 (9)	−0.0006 (9)	0.0045 (10)
C22B	0.0403 (10)	0.0442 (11)	0.0514 (12)	0.0011 (9)	−0.0024 (10)	0.0024 (10)
C23B	0.0372 (10)	0.0475 (11)	0.0522 (12)	0.0036 (8)	−0.0020 (10)	0.0029 (10)
C24B	0.0395 (10)	0.0472 (12)	0.0560 (13)	−0.0009 (9)	−0.0018 (10)	0.0043 (11)
C25B	0.0443 (12)	0.0453 (11)	0.0797 (18)	0.0025 (9)	0.0015 (13)	0.0065 (13)
C26B	0.0392 (11)	0.0497 (12)	0.0728 (16)	0.0063 (9)	0.0027 (12)	0.0047 (13)
O2W	0.185 (4)	0.116 (3)	0.109 (3)	0.057 (3)	0.006 (3)	0.010 (2)
O1W	0.137 (10)	0.149 (10)	0.123 (9)	0.021 (8)	0.000	0.000

Geometric parameters (Å, º) top

F1A—C9A	1.356 (3)	O2B—C6B	1.24 (2)
O1A—C2A	1.240 (3)	O2B—C4B	1.517 (17)
O2A—C4A	1.441 (3)	O3B—C6B	1.285 (17)
O2A—C6A	1.354 (3)	C6B—N2B	1.381 (12)
O3A—C6A	1.200 (4)	O2B'—C6B'	1.51 (3)
O4A—C14A	1.429 (4)	O2B'—C4B	1.31 (3)
O4A—C15A	1.430 (4)	O3B'—C6B'	1.11 (3)
N1A—C10A	1.423 (3)	C6B'—N2B	1.34 (2)
N1A—C13A	1.475 (4)	O4B—C14B	1.425 (4)
N1A—C16A	1.459 (4)	O4B—C15B	1.430 (4)
N2A—C5A	1.449 (3)	N1B—C10B	1.416 (3)
N2A—C6A	1.369 (3)	N1B—C13B	1.477 (3)
N2A—C7A	1.414 (3)	N1B—C16B	1.462 (3)
N3A—C2A	1.334 (3)	N2B—C5B	1.449 (3)
N3A—C3A	1.451 (3)	N2B—C7B	1.414 (3)
C1A—C2A	1.495 (4)	N3B—C2B	1.333 (3)
C3A—C4A	1.500 (4)	N3B—C3B	1.450 (3)
C4A—C5A	1.527 (3)	C1B—C2B	1.494 (4)
C7A—C8A	1.388 (4)	C3B—C4B	1.484 (4)
C7A—C12A	1.392 (3)	C4B—C5B	1.528 (3)
C8A—C9A	1.379 (3)	C7B—C8B	1.395 (4)
C9A—C10A	1.388 (4)	C7B—C12B	1.387 (3)
C10A—C11A	1.393 (4)	C8B—C9B	1.363 (4)
C11A—C12A	1.386 (3)	C9B—C10B	1.398 (3)
C13A—C14A	1.517 (4)	C10B—C11B	1.390 (3)
C15A—C16A	1.513 (4)	C11B—C12B	1.381 (3)
O5A—C20A	1.258 (3)	C13B—C14B	1.507 (4)
O6A—C20A	1.281 (3)	C15B—C16B	1.510 (3)
O7A—C23A	1.358 (3)	O5B—C20B	1.258 (3)
O8A—C24A	1.346 (3)	O6B—C20B	1.278 (3)
C20A—C21A	1.472 (3)	O7B—C23B	1.355 (3)
C21A—C22A	1.407 (3)	O8B—C24B	1.344 (3)
C21A—C26A	1.392 (4)	C20B—C21B	1.476 (3)
C22A—C23A	1.386 (3)	C21B—C22B	1.399 (3)
C23A—C24A	1.399 (4)	C21B—C26B	1.389 (4)
C24A—C25A	1.398 (3)	C22B—C23B	1.382 (3)
C25A—C26A	1.377 (4)	C23B—C24B	1.404 (4)
F1B—C9B	1.360 (3)	C24B—C25B	1.383 (3)
O1B—C2B	1.240 (3)	C25B—C26B	1.388 (4)

C6A—O2A—C4A	110.32 (19)	C4B—O2B'—C6B'	112.3 (15)
C14A—O4A—C15A	109.7 (2)	O3B'—C6B'—O2B'	120.2 (18)
C10A—N1A—C13A	113.6 (2)	O3B'—C6B'—N2B	136.3 (18)
C10A—N1A—C16A	114.7 (2)	N2B—C6B'—O2B'	103.4 (18)
C16A—N1A—C13A	110.1 (2)	C14B—O4B—C15B	109.1 (2)
C6A—N2A—C5A	111.3 (2)	C10B—N1B—C13B	114.1 (2)
C6A—N2A—C7A	126.0 (2)	C10B—N1B—C16B	114.2 (2)
C7A—N2A—C5A	122.4 (2)	C16B—N1B—C13B	110.1 (2)
C2A—N3A—C3A	123.0 (2)	C6B—N2B—C5B	109.1 (6)
O1A—C2A—N3A	122.3 (2)	C6B—N2B—C7B	128.4 (6)
O1A—C2A—C1A	121.2 (2)	C6B'—N2B—C5B	113.8 (9)
N3A—C2A—C1A	116.5 (2)	C6B'—N2B—C7B	122.7 (9)
N3A—C3A—C4A	113.0 (2)	C7B—N2B—C5B	122.1 (2)
O2A—C4A—C3A	109.6 (2)	C2B—N3B—C3B	122.6 (2)
O2A—C4A—C5A	104.5 (2)	O1B—C2B—N3B	121.4 (2)
C3A—C4A—C5A	113.1 (2)	O1B—C2B—C1B	121.8 (2)
N2A—C5A—C4A	102.0 (2)	N3B—C2B—C1B	116.8 (2)
O2A—C6A—N2A	109.3 (2)	N3B—C3B—C4B	111.4 (2)
O3A—C6A—O2A	121.7 (2)	O2B—C4B—C5B	103.2 (6)
O3A—C6A—N2A	128.9 (3)	O2B'—C4B—C3B	117.1 (9)
C8A—C7A—N2A	122.1 (2)	O2B'—C4B—C5B	107.1 (8)
C8A—C7A—C12A	118.7 (2)	C3B—C4B—O2B	104.1 (10)
C12A—C7A—N2A	119.2 (2)	C3B—C4B—C5B	114.6 (2)
C9A—C8A—C7A	118.6 (2)	N2B—C5B—C4B	102.5 (2)
F1A—C9A—C8A	117.3 (2)	C8B—C7B—N2B	122.6 (2)
F1A—C9A—C10A	117.9 (2)	C12B—C7B—N2B	119.1 (2)
C8A—C9A—C10A	124.8 (2)	C12B—C7B—C8B	118.3 (2)
C9A—C10A—N1A	120.1 (2)	C9B—C8B—C7B	118.8 (2)
C9A—C10A—C11A	115.1 (2)	F1B—C9B—C8B	117.0 (2)
C11A—C10A—N1A	124.7 (2)	F1B—C9B—C10B	117.8 (2)
C12A—C11A—C10A	121.9 (2)	C8B—C9B—C10B	125.2 (2)
C11A—C12A—C7A	120.9 (2)	C9B—C10B—N1B	121.5 (2)
N1A—C13A—C14A	110.1 (2)	C11B—C10B—N1B	124.4 (2)
O4A—C14A—C13A	111.2 (2)	C11B—C10B—C9B	114.1 (2)
O4A—C15A—C16A	110.8 (3)	C12B—C11B—C10B	122.7 (2)
N1A—C16A—C15A	109.5 (2)	C11B—C12B—C7B	120.8 (2)
O5A—C20A—O6A	122.4 (2)	N1B—C13B—C14B	110.5 (2)
O5A—C20A—C21A	120.8 (2)	O4B—C14B—C13B	110.7 (2)
O6A—C20A—C21A	116.8 (2)	O4B—C15B—C16B	110.2 (2)
C22A—C21A—C20A	120.7 (2)	N1B—C16B—C15B	110.2 (2)
C26A—C21A—C20A	119.2 (2)	O5B—C20B—O6B	122.4 (2)
C26A—C21A—C22A	120.0 (2)	O5B—C20B—C21B	119.9 (2)
C23A—C22A—C21A	119.4 (2)	O6B—C20B—C21B	117.7 (2)
O7A—C23A—C22A	125.1 (2)	C22B—C21B—C20B	120.0 (2)
O7A—C23A—C24A	114.6 (2)	C26B—C21B—C20B	120.2 (2)
C22A—C23A—C24A	120.3 (2)	C26B—C21B—C22B	119.7 (2)
O8A—C24A—C23A	121.8 (2)	C23B—C22B—C21B	120.2 (2)
O8A—C24A—C25A	118.4 (2)	O7B—C23B—C22B	124.7 (2)
C25A—C24A—C23A	119.8 (2)	O7B—C23B—C24B	115.3 (2)
C26A—C25A—C24A	120.1 (2)	C22B—C23B—C24B	119.9 (2)
C25A—C26A—C21A	120.4 (2)	O8B—C24B—C23B	121.7 (2)
C6B—O2B—C4B	109.3 (10)	O8B—C24B—C25B	118.7 (2)
O2B—C6B—O3B	121.8 (11)	C25B—C24B—C23B	119.6 (2)
O2B—C6B—N2B	114.6 (11)	C24B—C25B—C26B	120.6 (2)
O3B—C6B—N2B	123.6 (11)	C25B—C26B—C21B	120.0 (2)

(LIN:GA:H2O) top

Crystal data top

C₁₆H₂₀FN₃O₄·C₇H₆O₅·H₂O	F(000) = 2208
M_r = 525.48	D_x = 1.425 Mg m⁻³
Monoclinic, P2₁	Cu Kα radiation, λ = 1.54184 Å
a = 16.78184 (17) Å	Cell parameters from 47167 reflections
b = 15.4762 (2) Å	θ = 2.6–75.3°
c = 19.59820 (18) Å	µ = 1.00 mm⁻¹
β = 105.7581 (10)°	T = 293 K
V = 4898.74 (9) Å³	Plate
Z = 8	0.43 × 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 Source	18059 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.042
Detector resolution: 4.1685 pixels mm^-1	θ_max = 75.6°, θ_min = 2.3°
ω scans	h = −20→21
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 = −19→18
T_min = 0.651, T_max = 1.000	l = −24→24
79440 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.079P)² + 0.3717P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.043	(Δ/σ)_max = 0.001
wR(F²) = 0.123	Δρ_max = 0.26 e Å⁻³
S = 1.04	Δρ_min = −0.21 e Å⁻³
19039 reflections	Extinction correction: SHELXL-2016/6 (Sheldrick 2016), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1366 parameters	Extinction coefficient: 0.00065 (8)
1 restraint	Absolute 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 methods	Absolute structure parameter: −0.01 (5)
Hydrogen site location: mixed

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1A	0.85466 (9)	0.33695 (17)	0.90939 (8)	0.0653 (5)
O1A	0.57304 (11)	0.32992 (19)	1.35952 (10)	0.0598 (6)
O2A	0.76777 (11)	0.34092 (17)	1.21054 (9)	0.0553 (5)
O3A	0.85403 (11)	0.37670 (19)	1.14612 (10)	0.0607 (6)
O4A	0.67657 (12)	0.31366 (17)	0.65540 (10)	0.0581 (5)
N1A	0.71023 (13)	0.34905 (16)	0.80259 (11)	0.0442 (5)
N2A	0.71886 (12)	0.33428 (18)	1.09350 (10)	0.0466 (5)
N3A	0.68591 (13)	0.34206 (19)	1.31926 (11)	0.0482 (5)
H3A	0.739115	0.340574	1.330463	0.058*
C1A	0.70453 (17)	0.3353 (3)	1.44559 (14)	0.0589 (8)
H1AA	0.684535	0.376574	1.473578	0.088*
H1AB	0.759810	0.350421	1.445000	0.088*
H1AC	0.704658	0.278747	1.465778	0.088*
C2A	0.64906 (15)	0.3355 (2)	1.37110 (13)	0.0456 (6)
C3A	0.64178 (15)	0.3516 (2)	1.24472 (12)	0.0484 (6)
H3AA	0.637494	0.412460	1.232307	0.058*
H3AB	0.586163	0.328768	1.236523	0.058*
C4A	0.68596 (14)	0.3047 (2)	1.19857 (12)	0.0472 (6)
H4A	0.690171	0.243150	1.210885	0.057*
C5A	0.64687 (15)	0.3151 (2)	1.11871 (13)	0.0526 (7)
H5AA	0.619780	0.262310	1.097754	0.063*
H5AB	0.607231	0.362159	1.108706	0.063*
C6A	0.78639 (15)	0.3525 (2)	1.14818 (13)	0.0473 (6)
C7A	0.71596 (15)	0.3393 (2)	1.02061 (12)	0.0438 (5)
C8A	0.78778 (15)	0.3352 (2)	0.99863 (13)	0.0453 (5)
H8A	0.839015	0.329573	1.031751	0.054*
C9A	0.78264 (15)	0.3393 (2)	0.92782 (14)	0.0453 (5)
C10A	0.70849 (15)	0.34520 (19)	0.87430 (13)	0.0429 (5)
C11A	0.63737 (16)	0.3494 (2)	0.89773 (14)	0.0530 (7)
H11A	0.586158	0.354296	0.864474	0.064*
C12A	0.64056 (16)	0.3464 (2)	0.96947 (14)	0.0546 (7)
H12A	0.591772	0.349155	0.983239	0.065*
C13A	0.73951 (17)	0.2695 (2)	0.77638 (14)	0.0507 (6)
H13A	0.699482	0.223625	0.774156	0.061*
H13B	0.791555	0.251711	0.808808	0.061*
C14A	0.75136 (17)	0.2843 (3)	0.70358 (14)	0.0563 (7)
H14A	0.794584	0.326891	0.706612	0.068*
H14B	0.768734	0.230834	0.686107	0.068*
C15A	0.6508 (2)	0.3928 (2)	0.68073 (15)	0.0578 (7)
H15A	0.600758	0.413487	0.647084	0.069*
H15B	0.693479	0.436226	0.684689	0.069*
C16A	0.63454 (17)	0.3798 (2)	0.75217 (13)	0.0507 (6)
H16A	0.617231	0.433888	0.768676	0.061*
H16B	0.590537	0.337878	0.748188	0.061*
F1B	0.60783 (12)	0.5816 (2)	0.87273 (10)	0.0898 (9)
O1B	0.34277 (11)	0.54703 (17)	1.32311 (11)	0.0551 (5)
O2B	0.53869 (11)	0.54409 (18)	1.17963 (9)	0.0592 (6)
O3B	0.62658 (12)	0.5470 (2)	1.11255 (11)	0.0782 (9)
O4B	0.43222 (13)	0.56037 (17)	0.62245 (10)	0.0603 (6)
N1B	0.46632 (15)	0.53988 (18)	0.77081 (11)	0.0504 (5)
N2B	0.48479 (13)	0.54446 (19)	1.06323 (11)	0.0514 (6)
N3B	0.46049 (13)	0.56864 (19)	1.29142 (12)	0.0534 (6)
H3B	0.513690	0.569124	1.305569	0.064*
C1B	0.47070 (16)	0.5295 (3)	1.41248 (15)	0.0566 (7)
H1BA	0.484011	0.582389	1.438686	0.085*
H1BB	0.520871	0.500964	1.410634	0.085*
H1BC	0.439908	0.492590	1.435428	0.085*
C2B	0.41973 (14)	0.54901 (19)	1.33872 (13)	0.0451 (5)
C3B	0.42189 (15)	0.5893 (2)	1.21766 (13)	0.0525 (6)
H3BA	0.434769	0.648582	1.208516	0.063*
H3BB	0.362261	0.584422	1.208222	0.063*
C4B	0.45109 (16)	0.5305 (2)	1.16924 (13)	0.0505 (6)
H4B	0.441024	0.470345	1.180068	0.061*
C5B	0.41277 (16)	0.5479 (3)	1.09039 (14)	0.0570 (7)
H5BA	0.372648	0.503857	1.068982	0.068*
H5BB	0.386436	0.604210	1.082623	0.068*
C6B	0.55648 (16)	0.5457 (2)	1.11681 (14)	0.0543 (7)
C7B	0.47945 (15)	0.5459 (2)	0.98982 (13)	0.0484 (6)
C8B	0.54722 (17)	0.5669 (3)	0.96537 (15)	0.0574 (7)
H8B	0.597286	0.582362	0.997007	0.069*
C9B	0.53940 (17)	0.5644 (2)	0.89411 (15)	0.0554 (7)
C10B	0.46645 (17)	0.5442 (2)	0.84273 (14)	0.0489 (6)
C11B	0.39932 (19)	0.5253 (3)	0.86878 (16)	0.0639 (9)
H11B	0.348662	0.512205	0.836953	0.077*
C12B	0.40546 (18)	0.5253 (3)	0.94078 (15)	0.0643 (9)
H12B	0.359397	0.511398	0.956317	0.077*
C13B	0.4794 (2)	0.6228 (2)	0.73937 (15)	0.0554 (7)
H13C	0.525185	0.653308	0.771166	0.066*
H13D	0.430185	0.658323	0.732094	0.066*
C14B	0.49818 (19)	0.6070 (3)	0.66951 (14)	0.0586 (7)
H14C	0.505868	0.661836	0.648196	0.070*
H14D	0.549175	0.574266	0.677354	0.070*
C15B	0.4166 (2)	0.4807 (3)	0.65312 (16)	0.0644 (8)
H15C	0.464903	0.443723	0.660382	0.077*
H15D	0.370509	0.451522	0.620582	0.077*
C16B	0.3968 (2)	0.4945 (2)	0.72348 (15)	0.0586 (7)
H16C	0.346607	0.528389	0.716464	0.070*
H16D	0.388326	0.439287	0.743898	0.070*
F1C	−0.11287 (11)	0.3385 (2)	0.62387 (10)	0.0934 (9)
O1C	0.15341 (11)	0.38778 (17)	0.17495 (10)	0.0533 (5)
O2C	−0.04082 (11)	0.33573 (18)	0.31718 (9)	0.0576 (5)
O3C	−0.12912 (11)	0.35481 (19)	0.38285 (11)	0.0629 (6)
O4C	0.06624 (13)	0.36872 (16)	0.87343 (10)	0.0580 (5)
N1C	0.02964 (14)	0.38386 (17)	0.72409 (11)	0.0483 (5)
N2C	0.01228 (12)	0.34506 (19)	0.43328 (11)	0.0501 (5)
N3C	0.03619 (14)	0.3846 (2)	0.20955 (12)	0.0578 (6)
H3C	−0.016748	0.378804	0.196226	0.069*
C1C	0.02484 (16)	0.3895 (3)	0.08468 (14)	0.0555 (7)
H1CA	0.046821	0.432234	0.059232	0.083*
H1CB	−0.031161	0.404204	0.083269	0.083*
H1CC	0.025856	0.333960	0.063157	0.083*
C2C	0.07642 (14)	0.38667 (19)	0.16027 (13)	0.0440 (5)
C3C	0.07638 (18)	0.3917 (3)	0.28519 (14)	0.0633 (8)
H3CA	0.065923	0.448706	0.301395	0.076*
H3CB	0.135722	0.385558	0.293073	0.076*
C4C	0.04696 (15)	0.3255 (2)	0.32765 (13)	0.0516 (6)
H4C	0.058774	0.267540	0.312801	0.062*
C5C	0.08495 (16)	0.3361 (3)	0.40775 (14)	0.0614 (8)
H5CA	0.117144	0.285688	0.428028	0.074*
H5CB	0.119800	0.387010	0.418337	0.074*
C6C	−0.05850 (15)	0.3458 (2)	0.37955 (13)	0.0474 (6)
C7C	0.01727 (15)	0.3549 (2)	0.50625 (14)	0.0479 (6)
C8C	−0.05089 (16)	0.3392 (3)	0.53171 (14)	0.0565 (7)
H8C	−0.100835	0.321598	0.501018	0.068*
C9C	−0.04390 (17)	0.3499 (3)	0.60240 (15)	0.0557 (7)
C1OC	0.02899 (17)	0.3734 (2)	0.65227 (13)	0.0472 (6)
C11C	0.09652 (18)	0.3878 (3)	0.62541 (15)	0.0598 (8)
H11C	0.146915	0.403778	0.656328	0.072*
C12C	0.09079 (17)	0.3790 (3)	0.55376 (15)	0.0609 (8)
H12C	0.137083	0.389526	0.537551	0.073*
C13C	0.01166 (19)	0.3047 (2)	0.75796 (14)	0.0534 (6)
H13E	0.057919	0.265058	0.764740	0.064*
H13F	−0.036929	0.276890	0.727592	0.064*
C14C	−0.00335 (18)	0.3254 (2)	0.82867 (14)	0.0546 (7)
H14E	−0.052023	0.361769	0.821493	0.066*
H14F	−0.013579	0.272388	0.851278	0.066*
C15C	0.0852 (2)	0.4455 (2)	0.84039 (16)	0.0621 (8)
H15E	0.133460	0.473010	0.871492	0.075*
H15F	0.039134	0.485495	0.833116	0.075*
C16D	0.1019 (2)	0.4261 (2)	0.77005 (15)	0.0570 (7)
H16E	0.113293	0.479308	0.748295	0.068*
H16F	0.149833	0.388719	0.777137	0.068*
F1D	−0.35577 (10)	0.59351 (18)	0.58997 (9)	0.0713 (6)
O1D	−0.07886 (12)	0.6060 (2)	0.14188 (10)	0.0657 (7)
O2D	−0.26878 (11)	0.55280 (16)	0.28991 (9)	0.0539 (5)
O3D	−0.36038 (11)	0.55366 (18)	0.35378 (10)	0.0597 (6)
O4D	−0.17975 (13)	0.61932 (16)	0.84391 (10)	0.0574 (5)
N1D	−0.21292 (13)	0.57918 (17)	0.69762 (11)	0.0454 (5)
N2D	−0.21944 (12)	0.56266 (17)	0.40668 (11)	0.0459 (5)
N3D	−0.19271 (13)	0.5891 (2)	0.17980 (12)	0.0517 (6)
H3D	−0.244236	0.575107	0.167919	0.062*
C1D	−0.20443 (18)	0.5706 (3)	0.05537 (14)	0.0580 (7)
H1DA	−0.223856	0.623753	0.031303	0.087*
H1DB	−0.250916	0.535510	0.057343	0.087*
H1DC	−0.171351	0.540247	0.030183	0.087*
C2D	−0.15313 (16)	0.5899 (2)	0.12925 (14)	0.0474 (6)
C3D	−0.15429 (16)	0.6105 (2)	0.25373 (13)	0.0513 (6)
H3DA	−0.170167	0.668593	0.263205	0.062*
H3DB	−0.094557	0.609231	0.262605	0.062*
C4D	−0.17960 (15)	0.5484 (2)	0.30280 (12)	0.0472 (6)
H4D	−0.163255	0.489593	0.293839	0.057*
C5D	−0.14561 (16)	0.5700 (2)	0.38161 (14)	0.0531 (7)
H5DA	−0.103359	0.529127	0.405365	0.064*
H5DB	−0.122921	0.628036	0.388361	0.064*
C6D	−0.28911 (15)	0.5564 (2)	0.35157 (13)	0.0452 (6)
C7D	−0.21725 (15)	0.56874 (19)	0.47952 (13)	0.0429 (5)
C8D	−0.28923 (15)	0.5805 (2)	0.50089 (13)	0.0474 (6)
H8D	−0.340210	0.586006	0.467408	0.057*
C9D	−0.28394 (15)	0.5837 (2)	0.57175 (14)	0.0472 (6)
C10D	−0.21024 (16)	0.57771 (18)	0.62589 (13)	0.0433 (5)
C11D	−0.13979 (16)	0.5666 (2)	0.60292 (14)	0.0537 (7)
H11D	−0.088774	0.562119	0.636512	0.064*
C12D	−0.14261 (15)	0.5618 (2)	0.53159 (14)	0.0529 (7)
H12D	−0.093853	0.553764	0.518486	0.064*
C13D	−0.23736 (18)	0.6623 (2)	0.72141 (14)	0.0524 (6)
H13G	−0.287637	0.682697	0.687953	0.063*
H13H	−0.194158	0.704715	0.723600	0.063*
C14D	−0.25179 (18)	0.6520 (3)	0.79412 (15)	0.0595 (8)
H14G	−0.266349	0.707518	0.810325	0.071*
H14H	−0.297692	0.612724	0.790974	0.071*
C15D	−0.1574 (2)	0.5374 (2)	0.82034 (15)	0.0569 (7)
H15G	−0.202323	0.496706	0.816674	0.068*
H15H	−0.108858	0.515196	0.854847	0.068*
C1	−0.13939 (17)	0.5457 (2)	0.74908 (13)	0.0501 (6)
H1A	−0.093124	0.584664	0.752785	0.060*
H1B	−0.124794	0.489715	0.733787	0.060*
O5A	0.30459 (12)	0.26268 (19)	0.67903 (10)	0.0618 (6)
H5A	0.302638	0.263003	0.720382	0.093*
O6A	0.43937 (12)	0.24833 (17)	0.73113 (10)	0.0565 (5)
O7A	0.28178 (12)	0.3144 (2)	0.42462 (10)	0.0648 (7)
H7A	0.299367	0.331379	0.391820	0.097*
O8A	0.44016 (11)	0.30791 (17)	0.41204 (9)	0.0542 (5)
H8AA	0.489722	0.303900	0.415059	0.081*
O9A	0.56896 (11)	0.2723 (2)	0.52600 (10)	0.0624 (6)
H9A	0.603994	0.273184	0.564422	0.094*
C20A	0.38139 (16)	0.25756 (19)	0.67720 (13)	0.0451 (5)
C21A	0.39562 (15)	0.26645 (18)	0.60661 (12)	0.0422 (5)
C22A	0.33044 (15)	0.2846 (2)	0.54709 (13)	0.0459 (6)
H22A	0.276497	0.287965	0.550939	0.055*
C23A	0.34657 (15)	0.2976 (2)	0.48210 (13)	0.0460 (6)
C24A	0.42745 (15)	0.29359 (19)	0.47674 (12)	0.0428 (5)
C25A	0.49230 (15)	0.2750 (2)	0.53648 (12)	0.0444 (5)
C26A	0.47628 (15)	0.26100 (19)	0.60113 (12)	0.0439 (5)
H26A	0.519398	0.247963	0.640876	0.053*
O5B	0.42822 (13)	0.2554 (2)	0.86314 (11)	0.0656 (6)
H5B	0.430404	0.248820	0.822174	0.098*
O6B	0.29499 (13)	0.2752 (2)	0.80878 (10)	0.0698 (7)
O7B	0.16646 (12)	0.3507 (2)	1.00616 (10)	0.0681 (7)
H7B	0.131625	0.347489	0.967726	0.102*
O8B	0.29231 (11)	0.35176 (17)	1.12392 (9)	0.0556 (5)
H8BA	0.242366	0.355339	1.119273	0.083*
O9B	0.45012 (12)	0.3073 (2)	1.11953 (10)	0.0695 (7)
H9B	0.432367	0.316081	1.153980	0.104*
C20B	0.35244 (17)	0.2725 (2)	0.86342 (13)	0.0497 (6)
C21B	0.33801 (16)	0.2895 (2)	0.93318 (13)	0.0463 (6)
C22B	0.25779 (16)	0.3089 (2)	0.93482 (13)	0.0520 (7)
H22B	0.214890	0.307993	0.893199	0.062*
C23B	0.24187 (15)	0.3294 (2)	0.99814 (13)	0.0481 (6)
C24B	0.30578 (15)	0.3297 (2)	1.06082 (12)	0.0452 (6)
C25B	0.38631 (15)	0.3081 (2)	1.05959 (13)	0.0487 (6)
C26B	0.40212 (15)	0.2881 (2)	0.99554 (13)	0.0504 (6)
H26B	0.455512	0.273738	0.994259	0.060*
O5C	0.05396 (13)	0.66381 (17)	0.76876 (10)	0.0585 (5)
O6C	0.18882 (12)	0.6458 (2)	0.81926 (11)	0.0623 (6)
H6C	0.189165	0.641109	0.777663	0.094*
O7C	−0.07304 (12)	0.6564 (2)	0.97511 (10)	0.0619 (6)
H7C	−0.108280	0.653275	0.936897	0.093*
O8C	0.05512 (11)	0.61896 (17)	1.08888 (9)	0.0554 (5)
H8CA	0.005325	0.620692	1.085370	0.083*
O9C	0.21367 (12)	0.6092 (2)	1.07597 (11)	0.0682 (7)
H9C	0.197016	0.607037	1.111589	0.102*
C20C	0.11344 (17)	0.65600 (19)	0.82270 (13)	0.0460 (5)
C21C	0.10003 (16)	0.65312 (18)	0.89390 (13)	0.0431 (5)
C22C	0.01945 (16)	0.66215 (19)	0.89938 (13)	0.0454 (5)
H22C	−0.023401	0.675970	0.859659	0.054*
C23C	0.00378 (16)	0.65038 (19)	0.96446 (13)	0.0447 (5)
C24C	0.06792 (15)	0.63171 (19)	1.02425 (12)	0.0430 (5)
C25C	0.14915 (16)	0.6251 (2)	1.01863 (13)	0.0469 (6)
C26C	0.16473 (16)	0.6355 (2)	0.95329 (14)	0.0476 (6)
H26C	0.218491	0.630653	0.949242	0.057*
O5D	0.20197 (13)	0.6304 (2)	0.69097 (10)	0.0699 (7)
O6D	0.06747 (12)	0.64466 (19)	0.63859 (11)	0.0623 (6)
H6D	0.066460	0.650097	0.679963	0.093*
O7D	0.33074 (12)	0.5783 (2)	0.49035 (10)	0.0779 (9)
H7D	0.364431	0.573452	0.529244	0.117*
O8D	0.20394 (11)	0.57089 (19)	0.37371 (9)	0.0595 (6)
H8DA	0.253973	0.567719	0.378677	0.089*
O9D	0.04418 (13)	0.5987 (3)	0.38052 (11)	0.0855 (10)
H9D	0.061748	0.603503	0.345532	0.128*
C20D	0.14259 (17)	0.6320 (2)	0.63629 (14)	0.0491 (6)
C21D	0.15698 (16)	0.6176 (2)	0.56629 (13)	0.0454 (5)
C22D	0.23806 (16)	0.6060 (2)	0.56353 (13)	0.0532 (7)
H22D	0.281336	0.608518	0.604833	0.064*
C23D	0.25414 (15)	0.5905 (2)	0.49910 (13)	0.0500 (6)
C24D	0.18962 (15)	0.5872 (2)	0.43739 (12)	0.0460 (6)
C25D	0.10842 (16)	0.6009 (2)	0.43992 (14)	0.0534 (7)
C26D	0.09230 (16)	0.6162 (2)	0.50474 (14)	0.0528 (7)
H26D	0.038262	0.625438	0.506842	0.063*
O1W	0.06378 (14)	0.6137 (2)	0.25269 (11)	0.0731 (8)
H1WA	0.104934	0.597534	0.238495	0.110*
H1WB	0.021745	0.599983	0.219177	0.110*
O2W	0.43244 (13)	0.3191 (2)	0.24785 (10)	0.0776 (9)
H2WA	0.390001	0.326747	0.262887	0.116*
H2WB	0.473170	0.324798	0.284400	0.116*
O3W	0.20277 (12)	0.56091 (15)	0.20812 (11)	0.0539 (5)
H3WA	0.187470	0.501068	0.197492	0.081*
H3WB	0.248218	0.564788	0.240339	0.081*
O4W	0.29337 (12)	0.37097 (16)	0.29272 (11)	0.0539 (5)
H4WA	0.304195	0.423578	0.303797	0.081*
H4WB	0.252469	0.372894	0.255934	0.081*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1A	0.0375 (7)	0.1198 (16)	0.0432 (8)	−0.0019 (9)	0.0188 (6)	0.0042 (9)
O1A	0.0353 (8)	0.1080 (18)	0.0383 (9)	−0.0053 (10)	0.0138 (7)	0.0006 (10)
O2A	0.0377 (8)	0.0974 (16)	0.0334 (8)	−0.0033 (9)	0.0141 (7)	−0.0021 (9)
O3A	0.0366 (9)	0.1054 (18)	0.0411 (9)	−0.0113 (10)	0.0125 (7)	−0.0045 (10)
O4A	0.0505 (10)	0.0856 (16)	0.0369 (9)	0.0030 (10)	0.0094 (7)	−0.0054 (9)
N1A	0.0438 (10)	0.0558 (13)	0.0338 (9)	0.0029 (9)	0.0120 (8)	0.0026 (9)
N2A	0.0356 (9)	0.0740 (15)	0.0324 (9)	−0.0027 (9)	0.0129 (7)	0.0009 (9)
N3A	0.0317 (9)	0.0789 (16)	0.0359 (10)	0.0038 (9)	0.0121 (8)	0.0040 (10)
C1A	0.0431 (13)	0.098 (2)	0.0359 (12)	−0.0032 (14)	0.0108 (10)	0.0051 (14)
C2A	0.0353 (11)	0.0662 (16)	0.0366 (11)	0.0008 (11)	0.0124 (9)	0.0016 (11)
C3A	0.0394 (11)	0.0731 (18)	0.0340 (10)	0.0078 (11)	0.0121 (9)	0.0012 (11)
C4A	0.0386 (11)	0.0679 (17)	0.0384 (11)	0.0001 (11)	0.0163 (9)	0.0024 (11)
C5A	0.0368 (11)	0.088 (2)	0.0361 (11)	−0.0079 (12)	0.0159 (9)	−0.0032 (12)
C6A	0.0347 (11)	0.0729 (18)	0.0363 (11)	0.0020 (11)	0.0129 (9)	−0.0012 (11)
C7A	0.0385 (11)	0.0604 (15)	0.0338 (11)	0.0004 (10)	0.0122 (9)	0.0007 (10)
C8A	0.0354 (11)	0.0663 (16)	0.0353 (11)	−0.0005 (10)	0.0113 (9)	0.0039 (11)
C9A	0.0363 (11)	0.0627 (16)	0.0400 (12)	0.0001 (11)	0.0156 (9)	0.0038 (11)
C10A	0.0411 (12)	0.0542 (14)	0.0344 (11)	0.0005 (10)	0.0120 (9)	0.0026 (10)
C11A	0.0359 (11)	0.084 (2)	0.0388 (12)	0.0013 (12)	0.0096 (9)	0.0016 (13)
C12A	0.0352 (11)	0.089 (2)	0.0419 (13)	0.0023 (12)	0.0150 (10)	0.0003 (13)
C13A	0.0499 (14)	0.0589 (16)	0.0449 (13)	0.0037 (12)	0.0154 (11)	0.0010 (12)
C14A	0.0440 (13)	0.086 (2)	0.0409 (13)	0.0028 (13)	0.0147 (10)	−0.0049 (13)
C15A	0.0594 (16)	0.0725 (19)	0.0385 (13)	0.0027 (14)	0.0080 (11)	0.0066 (13)
C16A	0.0480 (13)	0.0657 (17)	0.0370 (12)	0.0089 (12)	0.0091 (10)	0.0017 (11)
F1B	0.0520 (10)	0.176 (3)	0.0459 (9)	−0.0246 (13)	0.0208 (8)	−0.0006 (13)
O1B	0.0329 (8)	0.0877 (15)	0.0468 (10)	−0.0063 (9)	0.0145 (7)	−0.0022 (10)
O2B	0.0425 (9)	0.1029 (17)	0.0343 (8)	0.0161 (10)	0.0137 (7)	0.0040 (10)
O3B	0.0397 (10)	0.154 (3)	0.0416 (10)	0.0144 (13)	0.0120 (8)	−0.0003 (13)
O4B	0.0565 (11)	0.0862 (16)	0.0352 (9)	0.0009 (10)	0.0071 (8)	−0.0026 (9)
N1B	0.0575 (12)	0.0589 (14)	0.0350 (10)	−0.0023 (11)	0.0130 (9)	−0.0014 (10)
N2B	0.0385 (10)	0.0827 (17)	0.0345 (10)	−0.0001 (10)	0.0126 (8)	0.0007 (10)
N3B	0.0312 (9)	0.0890 (18)	0.0425 (11)	−0.0054 (10)	0.0143 (8)	−0.0070 (11)
C1B	0.0392 (12)	0.084 (2)	0.0470 (14)	−0.0009 (13)	0.0130 (11)	0.0010 (14)
C2B	0.0336 (10)	0.0605 (15)	0.0438 (12)	−0.0047 (10)	0.0147 (9)	−0.0078 (11)
C3B	0.0383 (11)	0.0775 (19)	0.0444 (13)	0.0017 (12)	0.0160 (10)	−0.0013 (12)
C4B	0.0481 (13)	0.0654 (17)	0.0417 (12)	−0.0029 (12)	0.0184 (10)	−0.0010 (11)
C5B	0.0405 (12)	0.093 (2)	0.0396 (12)	−0.0036 (13)	0.0151 (10)	−0.0016 (13)
C6B	0.0409 (12)	0.086 (2)	0.0378 (12)	0.0121 (13)	0.0133 (10)	0.0026 (13)
C7B	0.0417 (12)	0.0682 (17)	0.0366 (12)	−0.0017 (11)	0.0128 (10)	0.0004 (11)
C8B	0.0437 (13)	0.089 (2)	0.0386 (13)	−0.0078 (14)	0.0105 (10)	−0.0008 (13)
C9B	0.0436 (13)	0.085 (2)	0.0407 (13)	−0.0070 (13)	0.0164 (11)	−0.0009 (13)
C10B	0.0489 (13)	0.0624 (17)	0.0355 (12)	−0.0005 (12)	0.0119 (10)	−0.0021 (11)
C11B	0.0500 (15)	0.100 (3)	0.0402 (13)	−0.0135 (16)	0.0089 (11)	−0.0039 (15)
C12B	0.0439 (13)	0.107 (3)	0.0429 (13)	−0.0148 (15)	0.0131 (11)	−0.0020 (15)
C13B	0.0677 (17)	0.0574 (17)	0.0432 (13)	−0.0053 (13)	0.0188 (12)	−0.0039 (12)
C14B	0.0560 (15)	0.080 (2)	0.0401 (13)	−0.0043 (14)	0.0141 (11)	0.0005 (13)
C15B	0.0706 (19)	0.074 (2)	0.0442 (14)	−0.0012 (16)	0.0085 (13)	−0.0119 (14)
C16B	0.0635 (17)	0.0663 (19)	0.0431 (13)	−0.0115 (14)	0.0094 (12)	−0.0047 (13)
F1C	0.0459 (9)	0.193 (3)	0.0477 (9)	−0.0131 (13)	0.0236 (7)	−0.0012 (14)
O1C	0.0367 (8)	0.0816 (14)	0.0423 (9)	−0.0049 (9)	0.0122 (7)	−0.0037 (9)
O2C	0.0367 (8)	0.1033 (17)	0.0346 (8)	−0.0037 (9)	0.0130 (6)	0.0015 (10)
O3C	0.0319 (8)	0.116 (2)	0.0421 (9)	0.0045 (10)	0.0115 (7)	0.0074 (11)
O4C	0.0611 (12)	0.0750 (15)	0.0352 (9)	0.0044 (10)	0.0082 (8)	0.0010 (9)
N1C	0.0550 (12)	0.0545 (13)	0.0361 (10)	−0.0026 (10)	0.0137 (9)	−0.0037 (9)
N2C	0.0336 (9)	0.0833 (17)	0.0349 (10)	0.0012 (10)	0.0117 (8)	−0.0026 (10)
N3C	0.0384 (10)	0.098 (2)	0.0401 (11)	−0.0156 (11)	0.0154 (8)	−0.0066 (12)
C1C	0.0428 (13)	0.083 (2)	0.0401 (13)	−0.0066 (13)	0.0103 (10)	−0.0011 (13)
C2C	0.0366 (11)	0.0575 (14)	0.0394 (11)	−0.0085 (10)	0.0128 (9)	−0.0027 (10)
C3C	0.0532 (14)	0.099 (2)	0.0393 (12)	−0.0223 (16)	0.0161 (11)	−0.0102 (14)
C4C	0.0382 (11)	0.0789 (19)	0.0403 (11)	−0.0001 (11)	0.0152 (9)	−0.0051 (12)
C5C	0.0361 (12)	0.112 (3)	0.0387 (12)	0.0014 (14)	0.0148 (10)	−0.0025 (15)
C6C	0.0361 (11)	0.0722 (17)	0.0356 (11)	−0.0001 (11)	0.0129 (9)	0.0043 (11)
C7C	0.0393 (12)	0.0680 (17)	0.0369 (11)	−0.0003 (11)	0.0110 (9)	−0.0020 (11)
C8C	0.0373 (12)	0.097 (2)	0.0372 (12)	−0.0057 (13)	0.0129 (9)	−0.0036 (14)
C9C	0.0392 (12)	0.090 (2)	0.0414 (13)	−0.0030 (13)	0.0162 (10)	−0.0019 (13)
C1OC	0.0490 (13)	0.0571 (16)	0.0368 (12)	0.0007 (11)	0.0140 (10)	−0.0009 (10)
C11C	0.0442 (14)	0.093 (2)	0.0411 (13)	−0.0121 (15)	0.0095 (11)	−0.0052 (15)
C12C	0.0412 (13)	0.101 (3)	0.0432 (13)	−0.0097 (14)	0.0154 (10)	−0.0053 (15)
C13C	0.0627 (15)	0.0559 (16)	0.0437 (13)	−0.0026 (12)	0.0183 (11)	−0.0017 (12)
C14C	0.0555 (15)	0.0696 (18)	0.0396 (12)	0.0010 (13)	0.0145 (11)	0.0025 (12)
C15C	0.076 (2)	0.0624 (19)	0.0450 (15)	−0.0058 (15)	0.0105 (13)	−0.0089 (13)
C16D	0.0639 (17)	0.0634 (18)	0.0431 (14)	−0.0089 (13)	0.0134 (12)	−0.0046 (12)
F1D	0.0406 (8)	0.1348 (19)	0.0439 (8)	0.0145 (10)	0.0209 (6)	0.0072 (10)
O1D	0.0397 (9)	0.121 (2)	0.0399 (9)	−0.0130 (11)	0.0165 (7)	−0.0028 (11)
O2D	0.0402 (9)	0.0901 (15)	0.0331 (8)	−0.0089 (9)	0.0131 (7)	−0.0011 (9)
O3D	0.0347 (9)	0.1040 (18)	0.0406 (9)	−0.0066 (10)	0.0107 (7)	0.0014 (10)
O4D	0.0558 (11)	0.0785 (14)	0.0367 (9)	0.0053 (10)	0.0107 (8)	−0.0052 (9)
N1D	0.0471 (11)	0.0568 (13)	0.0330 (10)	0.0057 (9)	0.0122 (8)	0.0043 (9)
N2D	0.0348 (9)	0.0720 (15)	0.0332 (9)	−0.0021 (9)	0.0130 (7)	0.0004 (9)
N3D	0.0361 (10)	0.0849 (17)	0.0372 (10)	−0.0012 (10)	0.0150 (8)	0.0030 (11)
C1D	0.0476 (14)	0.088 (2)	0.0388 (13)	−0.0039 (14)	0.0128 (11)	0.0009 (13)
C2D	0.0400 (12)	0.0663 (17)	0.0387 (12)	−0.0018 (11)	0.0157 (10)	0.0022 (11)
C3D	0.0425 (12)	0.0760 (19)	0.0389 (11)	−0.0072 (12)	0.0172 (9)	−0.0009 (12)
C4D	0.0398 (11)	0.0675 (17)	0.0366 (11)	0.0008 (11)	0.0144 (9)	0.0004 (11)
C5D	0.0381 (12)	0.088 (2)	0.0358 (11)	−0.0027 (12)	0.0153 (9)	0.0006 (12)
C6D	0.0371 (11)	0.0644 (16)	0.0358 (11)	−0.0039 (10)	0.0125 (9)	0.0021 (11)
C7D	0.0376 (11)	0.0571 (15)	0.0348 (11)	0.0016 (10)	0.0115 (9)	0.0021 (10)
C8D	0.0346 (11)	0.0713 (18)	0.0365 (12)	0.0053 (11)	0.0100 (9)	0.0041 (11)
C9D	0.0371 (11)	0.0699 (18)	0.0377 (12)	0.0064 (11)	0.0154 (9)	0.0058 (11)
C10D	0.0435 (12)	0.0543 (15)	0.0336 (11)	0.0031 (10)	0.0131 (9)	0.0037 (10)
C11D	0.0402 (12)	0.082 (2)	0.0382 (12)	0.0045 (12)	0.0096 (10)	0.0005 (13)
C12D	0.0356 (12)	0.087 (2)	0.0381 (12)	0.0027 (12)	0.0124 (10)	−0.0025 (13)
C13D	0.0580 (15)	0.0609 (17)	0.0406 (12)	0.0103 (13)	0.0173 (11)	0.0035 (12)
C14D	0.0526 (15)	0.086 (2)	0.0415 (13)	0.0111 (14)	0.0153 (11)	−0.0033 (14)
C15D	0.0621 (16)	0.0680 (19)	0.0369 (12)	0.0032 (14)	0.0072 (11)	0.0040 (12)
C1	0.0511 (14)	0.0593 (16)	0.0374 (12)	0.0062 (12)	0.0079 (10)	0.0016 (11)
O5A	0.0459 (10)	0.1063 (19)	0.0386 (9)	−0.0037 (10)	0.0210 (8)	−0.0031 (10)
O6A	0.0509 (10)	0.0865 (15)	0.0355 (9)	0.0052 (10)	0.0175 (8)	0.0026 (9)
O7A	0.0384 (9)	0.116 (2)	0.0392 (9)	0.0029 (11)	0.0092 (7)	0.0103 (11)
O8A	0.0397 (9)	0.0936 (16)	0.0314 (8)	−0.0009 (9)	0.0136 (7)	0.0053 (9)
O9A	0.0369 (9)	0.117 (2)	0.0361 (9)	0.0048 (10)	0.0142 (7)	0.0014 (11)
C20A	0.0447 (12)	0.0574 (15)	0.0366 (12)	−0.0031 (10)	0.0165 (10)	−0.0036 (10)
C21A	0.0434 (12)	0.0523 (14)	0.0344 (11)	−0.0037 (10)	0.0163 (9)	−0.0027 (10)
C22A	0.0372 (11)	0.0638 (16)	0.0388 (12)	−0.0032 (11)	0.0138 (9)	−0.0039 (11)
C23A	0.0389 (11)	0.0636 (16)	0.0355 (11)	−0.0033 (11)	0.0103 (9)	−0.0028 (11)
C24A	0.0429 (12)	0.0561 (14)	0.0317 (11)	−0.0024 (10)	0.0139 (9)	−0.0003 (10)
C25A	0.0370 (11)	0.0639 (16)	0.0346 (11)	0.0012 (10)	0.0137 (9)	−0.0022 (10)
C26A	0.0429 (12)	0.0572 (15)	0.0324 (11)	0.0020 (10)	0.0114 (9)	0.0002 (10)
O5B	0.0514 (11)	0.1090 (19)	0.0420 (10)	0.0089 (11)	0.0223 (8)	−0.0045 (11)
O6B	0.0483 (10)	0.127 (2)	0.0362 (9)	−0.0007 (12)	0.0151 (8)	−0.0113 (11)
O7B	0.0388 (9)	0.132 (2)	0.0343 (9)	0.0128 (11)	0.0111 (7)	−0.0070 (11)
O8B	0.0410 (9)	0.0966 (16)	0.0305 (8)	0.0065 (10)	0.0120 (7)	−0.0053 (9)
O9B	0.0399 (9)	0.131 (2)	0.0358 (9)	0.0114 (12)	0.0073 (7)	−0.0066 (12)
C20B	0.0454 (13)	0.0705 (18)	0.0366 (12)	−0.0018 (12)	0.0171 (10)	−0.0027 (11)
C21B	0.0441 (12)	0.0640 (16)	0.0338 (11)	0.0001 (11)	0.0155 (9)	−0.0023 (11)
C22B	0.0437 (12)	0.082 (2)	0.0311 (11)	0.0008 (12)	0.0110 (9)	−0.0017 (12)
C23B	0.0378 (12)	0.0749 (18)	0.0336 (11)	0.0024 (11)	0.0133 (9)	0.0000 (11)
C24B	0.0416 (12)	0.0645 (16)	0.0314 (11)	0.0006 (11)	0.0135 (9)	−0.0011 (11)
C25B	0.0398 (12)	0.0728 (18)	0.0336 (11)	0.0023 (11)	0.0103 (9)	−0.0009 (11)
C26B	0.0389 (12)	0.0753 (18)	0.0396 (12)	0.0044 (12)	0.0150 (9)	−0.0028 (12)
O5C	0.0558 (11)	0.0872 (16)	0.0360 (9)	0.0035 (10)	0.0184 (8)	0.0073 (9)
O6C	0.0492 (10)	0.1029 (18)	0.0406 (9)	−0.0104 (11)	0.0219 (8)	−0.0055 (11)
O7C	0.0434 (10)	0.1077 (19)	0.0382 (9)	0.0103 (11)	0.0170 (8)	0.0016 (11)
O8C	0.0443 (9)	0.0943 (16)	0.0306 (8)	−0.0015 (10)	0.0151 (7)	0.0022 (9)
O9C	0.0422 (9)	0.124 (2)	0.0387 (10)	−0.0010 (12)	0.0115 (8)	0.0069 (12)
C20C	0.0509 (13)	0.0522 (14)	0.0388 (12)	−0.0066 (11)	0.0186 (10)	−0.0023 (10)
C21C	0.0485 (13)	0.0495 (13)	0.0358 (11)	−0.0053 (10)	0.0191 (10)	−0.0031 (10)
C22C	0.0472 (12)	0.0560 (15)	0.0355 (11)	0.0012 (11)	0.0155 (9)	−0.0008 (10)
C23C	0.0452 (12)	0.0572 (15)	0.0349 (11)	0.0021 (11)	0.0162 (9)	−0.0018 (10)
C24C	0.0433 (12)	0.0579 (15)	0.0308 (11)	−0.0042 (10)	0.0151 (9)	−0.0029 (10)
C25C	0.0415 (12)	0.0650 (16)	0.0352 (11)	−0.0039 (11)	0.0120 (9)	−0.0015 (11)
C26C	0.0421 (12)	0.0642 (17)	0.0398 (12)	−0.0071 (11)	0.0167 (10)	−0.0037 (11)
O5D	0.0529 (11)	0.125 (2)	0.0344 (9)	0.0052 (13)	0.0163 (8)	−0.0064 (11)
O6D	0.0503 (10)	0.1003 (17)	0.0429 (10)	0.0063 (11)	0.0242 (8)	−0.0037 (10)
O7D	0.0366 (9)	0.163 (3)	0.0354 (9)	0.0095 (13)	0.0118 (7)	−0.0088 (13)
O8D	0.0391 (9)	0.1107 (19)	0.0303 (8)	0.0035 (10)	0.0124 (7)	−0.0065 (10)
O9D	0.0370 (9)	0.179 (3)	0.0391 (10)	0.0062 (14)	0.0075 (8)	−0.0130 (15)
C20D	0.0445 (12)	0.0670 (17)	0.0387 (12)	−0.0009 (11)	0.0161 (10)	−0.0017 (11)
C21D	0.0431 (12)	0.0608 (15)	0.0353 (11)	−0.0015 (11)	0.0158 (9)	−0.0009 (11)
C22D	0.0417 (12)	0.086 (2)	0.0323 (11)	0.0025 (13)	0.0113 (9)	−0.0036 (12)
C23D	0.0373 (12)	0.0787 (19)	0.0355 (12)	0.0033 (12)	0.0127 (10)	−0.0014 (12)
C24D	0.0414 (12)	0.0686 (17)	0.0304 (11)	−0.0002 (11)	0.0138 (9)	−0.0026 (11)
C25D	0.0374 (12)	0.088 (2)	0.0351 (12)	0.0012 (12)	0.0098 (9)	−0.0028 (13)
C26D	0.0390 (12)	0.082 (2)	0.0409 (12)	−0.0005 (12)	0.0164 (10)	−0.0035 (13)
O1W	0.0535 (11)	0.122 (2)	0.0415 (10)	0.0275 (14)	0.0091 (9)	−0.0030 (12)
O2W	0.0470 (10)	0.150 (3)	0.0340 (9)	0.0199 (14)	0.0082 (8)	−0.0002 (13)
O3W	0.0424 (9)	0.0723 (14)	0.0444 (10)	−0.0017 (9)	0.0070 (7)	0.0050 (9)
O4W	0.0440 (9)	0.0713 (13)	0.0421 (9)	0.0011 (9)	0.0045 (7)	0.0042 (9)

Geometric parameters (Å, º) top

F1A—C9A	1.353 (3)	C13C—C14C	1.509 (4)
O1A—C2A	1.236 (3)	C15C—C16D	1.510 (4)
O2A—C4A	1.442 (3)	F1D—C9D	1.356 (3)
O2A—C6A	1.353 (3)	O1D—C2D	1.229 (3)
O3A—C6A	1.206 (3)	O2D—C4D	1.450 (3)
O4A—C14A	1.425 (3)	O2D—C6D	1.343 (3)
O4A—C15A	1.432 (4)	O3D—C6D	1.209 (3)
N1A—C10A	1.415 (3)	O4D—C14D	1.424 (4)
N1A—C13A	1.469 (4)	O4D—C15D	1.433 (4)
N1A—C16A	1.461 (3)	N1D—C10D	1.419 (3)
N2A—C5A	1.455 (3)	N1D—C13D	1.465 (4)
N2A—C6A	1.361 (3)	N1D—C1	1.460 (3)
N2A—C7A	1.418 (3)	N2D—C5D	1.456 (3)
N3A—C2A	1.329 (3)	N2D—C6D	1.363 (3)
N3A—C3A	1.455 (3)	N2D—C7D	1.421 (3)
C1A—C2A	1.503 (3)	N3D—C2D	1.334 (3)
C3A—C4A	1.503 (3)	N3D—C3D	1.455 (3)
C4A—C5A	1.532 (3)	C1D—C2D	1.500 (4)
C7A—C8A	1.387 (3)	C3D—C4D	1.500 (4)
C7A—C12A	1.389 (3)	C4D—C5D	1.531 (3)
C8A—C9A	1.368 (3)	C7D—C8D	1.394 (3)
C9A—C10A	1.396 (3)	C7D—C12D	1.388 (3)
C10A—C11A	1.392 (4)	C8D—C9D	1.368 (4)
C11A—C12A	1.393 (4)	C9D—C10D	1.397 (3)
C13A—C14A	1.511 (4)	C10D—C11D	1.385 (4)
C15A—C16A	1.511 (4)	C11D—C12D	1.388 (4)
F1B—C9B	1.351 (3)	C13D—C14D	1.517 (4)
O1B—C2B	1.244 (3)	C15D—C1	1.513 (4)
O2B—C4B	1.444 (3)	O5A—C20A	1.301 (3)
O2B—C6B	1.344 (3)	O6A—C20A	1.235 (3)
O3B—C6B	1.202 (3)	O7A—C23A	1.361 (3)
O4B—C14B	1.429 (4)	O8A—C24A	1.360 (3)
O4B—C15B	1.427 (5)	O9A—C25A	1.357 (3)
N1B—C10B	1.410 (3)	C20A—C21A	1.473 (3)
N1B—C13B	1.466 (4)	C21A—C22A	1.394 (4)
N1B—C16B	1.459 (4)	C21A—C26A	1.389 (3)
N2B—C5B	1.448 (3)	C22A—C23A	1.387 (3)
N2B—C6B	1.365 (3)	C23A—C24A	1.391 (3)
N2B—C7B	1.417 (3)	C24A—C25A	1.395 (3)
N3B—C2B	1.328 (3)	C25A—C26A	1.382 (3)
N3B—C3B	1.450 (3)	O5B—C20B	1.300 (3)
C1B—C2B	1.497 (4)	O6B—C20B	1.232 (3)
C3B—C4B	1.490 (4)	O7B—C23B	1.357 (3)
C4B—C5B	1.528 (4)	O8B—C24B	1.360 (3)
C7B—C8B	1.387 (4)	O9B—C25B	1.358 (3)
C7B—C12B	1.385 (4)	C20B—C21B	1.475 (3)
C8B—C9B	1.367 (4)	C21B—C22B	1.388 (4)
C9B—C10B	1.393 (4)	C21B—C26B	1.392 (3)
C10B—C11B	1.388 (4)	C22B—C23B	1.376 (3)
C11B—C12B	1.387 (4)	C23B—C24B	1.394 (3)
C13B—C14B	1.506 (4)	C24B—C25B	1.399 (3)
C15B—C16B	1.519 (4)	C25B—C26B	1.387 (3)
F1C—C9C	1.346 (3)	O5C—C20C	1.247 (3)
O1C—C2C	1.245 (3)	O6C—C20C	1.295 (3)
O2C—C4C	1.440 (3)	O7C—C23C	1.364 (3)
O2C—C6C	1.343 (3)	O8C—C24C	1.356 (3)
O3C—C6C	1.212 (3)	O9C—C25C	1.354 (3)
O4C—C14C	1.423 (4)	C20C—C21C	1.473 (3)
O4C—C15C	1.430 (4)	C21C—C22C	1.392 (3)
N1C—C1OC	1.414 (3)	C21C—C26C	1.386 (4)
N1C—C13C	1.463 (4)	C22C—C23C	1.382 (3)
N1C—C16D	1.454 (4)	C23C—C24C	1.389 (3)
N2C—C5C	1.445 (3)	C24C—C25C	1.401 (3)
N2C—C6C	1.357 (3)	C25C—C26C	1.384 (3)
N2C—C7C	1.418 (3)	O5D—C20D	1.250 (3)
N3C—C2C	1.321 (3)	O6D—C20D	1.289 (3)
N3C—C3C	1.456 (3)	O7D—C23D	1.355 (3)
C1C—C2C	1.500 (3)	O8D—C24D	1.357 (3)
C3C—C4C	1.486 (4)	O9D—C25D	1.355 (3)
C4C—C5C	1.534 (3)	C20D—C21D	1.473 (3)
C7C—C8C	1.388 (4)	C21D—C22D	1.388 (3)
C7C—C12C	1.380 (4)	C21D—C26D	1.387 (4)
C8C—C9C	1.368 (4)	C22D—C23D	1.382 (3)
C9C—C1OC	1.391 (4)	C23D—C24D	1.388 (3)
C1OC—C11C	1.391 (4)	C24D—C25D	1.393 (3)
C11C—C12C	1.388 (4)	C25D—C26D	1.389 (3)

C6A—O2A—C4A	110.35 (18)	O4C—C15C—C16D	111.6 (3)
C14A—O4A—C15A	109.8 (2)	N1C—C16D—C15C	109.0 (3)
C10A—N1A—C13A	114.3 (2)	C6D—O2D—C4D	110.33 (18)
C10A—N1A—C16A	115.9 (2)	C14D—O4D—C15D	109.9 (2)
C16A—N1A—C13A	110.4 (2)	C10D—N1D—C13D	114.6 (2)
C6A—N2A—C5A	111.44 (19)	C10D—N1D—C1	115.5 (2)
C6A—N2A—C7A	125.1 (2)	C1—N1D—C13D	110.4 (2)
C7A—N2A—C5A	123.3 (2)	C6D—N2D—C5D	111.33 (19)
C2A—N3A—C3A	124.0 (2)	C6D—N2D—C7D	125.7 (2)
O1A—C2A—N3A	122.4 (2)	C7D—N2D—C5D	122.8 (2)
O1A—C2A—C1A	120.9 (2)	C2D—N3D—C3D	124.2 (2)
N3A—C2A—C1A	116.7 (2)	O1D—C2D—N3D	122.3 (3)
N3A—C3A—C4A	110.8 (2)	O1D—C2D—C1D	121.3 (2)
O2A—C4A—C3A	108.5 (2)	N3D—C2D—C1D	116.4 (2)
O2A—C4A—C5A	104.46 (18)	N3D—C3D—C4D	111.5 (2)
C3A—C4A—C5A	114.8 (2)	O2D—C4D—C3D	108.5 (2)
N2A—C5A—C4A	101.76 (19)	O2D—C4D—C5D	104.46 (19)
O2A—C6A—N2A	109.7 (2)	C3D—C4D—C5D	114.4 (2)
O3A—C6A—O2A	121.4 (2)	N2D—C5D—C4D	101.8 (2)
O3A—C6A—N2A	128.9 (2)	O2D—C6D—N2D	110.1 (2)
C8A—C7A—N2A	121.0 (2)	O3D—C6D—O2D	121.7 (2)
C8A—C7A—C12A	118.5 (2)	O3D—C6D—N2D	128.2 (2)
C12A—C7A—N2A	120.4 (2)	C8D—C7D—N2D	121.5 (2)
C9A—C8A—C7A	119.5 (2)	C12D—C7D—N2D	120.3 (2)
F1A—C9A—C8A	117.0 (2)	C12D—C7D—C8D	118.2 (2)
F1A—C9A—C10A	118.7 (2)	C9D—C8D—C7D	119.2 (2)
C8A—C9A—C10A	124.3 (2)	F1D—C9D—C8D	117.0 (2)
C9A—C10A—N1A	119.6 (2)	F1D—C9D—C10D	118.3 (2)
C11A—C10A—N1A	125.2 (2)	C8D—C9D—C10D	124.6 (2)
C11A—C10A—C9A	115.1 (2)	C9D—C10D—N1D	119.5 (2)
C10A—C11A—C12A	122.0 (2)	C11D—C10D—N1D	125.7 (2)
C7A—C12A—C11A	120.6 (2)	C11D—C10D—C9D	114.8 (2)
N1A—C13A—C14A	110.2 (3)	C10D—C11D—C12D	122.4 (2)
O4A—C14A—C13A	110.9 (2)	C11D—C12D—C7D	120.9 (2)
O4A—C15A—C16A	110.8 (3)	N1D—C13D—C14D	109.7 (3)
N1A—C16A—C15A	109.1 (2)	O4D—C14D—C13D	111.0 (2)
C6B—O2B—C4B	110.2 (2)	O4D—C15D—C1	111.0 (3)
C15B—O4B—C14B	111.3 (2)	N1D—C1—C15D	108.9 (2)
C10B—N1B—C13B	114.8 (2)	O5A—C20A—C21A	115.8 (2)
C10B—N1B—C16B	116.2 (2)	O6A—C20A—O5A	122.6 (2)
C16B—N1B—C13B	109.9 (2)	O6A—C20A—C21A	121.6 (2)
C6B—N2B—C5B	111.5 (2)	C22A—C21A—C20A	121.0 (2)
C6B—N2B—C7B	125.4 (2)	C26A—C21A—C20A	118.5 (2)
C7B—N2B—C5B	122.9 (2)	C26A—C21A—C22A	120.5 (2)
C2B—N3B—C3B	124.8 (2)	C23A—C22A—C21A	119.6 (2)
O1B—C2B—N3B	122.1 (2)	O7A—C23A—C22A	118.5 (2)
O1B—C2B—C1B	121.0 (2)	O7A—C23A—C24A	121.5 (2)
N3B—C2B—C1B	116.9 (2)	C22A—C23A—C24A	120.0 (2)
N3B—C3B—C4B	111.4 (2)	O8A—C24A—C23A	117.8 (2)
O2B—C4B—C3B	108.6 (2)	O8A—C24A—C25A	122.1 (2)
O2B—C4B—C5B	104.47 (19)	C23A—C24A—C25A	120.0 (2)
C3B—C4B—C5B	114.6 (3)	O9A—C25A—C24A	115.8 (2)
N2B—C5B—C4B	101.6 (2)	O9A—C25A—C26A	124.2 (2)
O2B—C6B—N2B	109.6 (2)	C26A—C25A—C24A	120.0 (2)
O3B—C6B—O2B	122.0 (2)	C25A—C26A—C21A	119.8 (2)
O3B—C6B—N2B	128.4 (2)	O5B—C20B—C21B	116.5 (2)
C8B—C7B—N2B	121.5 (2)	O6B—C20B—O5B	122.6 (2)
C12B—C7B—N2B	119.9 (2)	O6B—C20B—C21B	120.9 (2)
C12B—C7B—C8B	118.6 (2)	C22B—C21B—C20B	117.7 (2)
C9B—C8B—C7B	119.1 (3)	C22B—C21B—C26B	120.4 (2)
F1B—C9B—C8B	117.2 (3)	C26B—C21B—C20B	121.9 (2)
F1B—C9B—C10B	118.3 (2)	C23B—C22B—C21B	119.9 (2)
C8B—C9B—C10B	124.5 (3)	O7B—C23B—C22B	125.2 (2)
C9B—C10B—N1B	119.7 (2)	O7B—C23B—C24B	114.5 (2)
C11B—C10B—N1B	125.2 (3)	C22B—C23B—C24B	120.3 (2)
C11B—C10B—C9B	115.0 (2)	O8B—C24B—C23B	121.6 (2)
C12B—C11B—C10B	122.0 (3)	O8B—C24B—C25B	118.4 (2)
C7B—C12B—C11B	120.7 (3)	C23B—C24B—C25B	120.0 (2)
N1B—C13B—C14B	109.4 (3)	O9B—C25B—C24B	121.7 (2)
O4B—C14B—C13B	110.6 (2)	O9B—C25B—C26B	118.8 (2)
O4B—C15B—C16B	111.8 (3)	C26B—C25B—C24B	119.5 (2)
N1B—C16B—C15B	108.1 (3)	C25B—C26B—C21B	119.9 (2)
C6C—O2C—C4C	110.70 (19)	O5C—C20C—O6C	122.4 (2)
C14C—O4C—C15C	111.0 (2)	O5C—C20C—C21C	120.8 (2)
C1OC—N1C—C13C	114.2 (2)	O6C—C20C—C21C	116.6 (2)
C1OC—N1C—C16D	116.6 (2)	C22C—C21C—C20C	118.1 (2)
C16D—N1C—C13C	109.6 (2)	C26C—C21C—C20C	121.0 (2)
C6C—N2C—C5C	112.1 (2)	C26C—C21C—C22C	120.7 (2)
C6C—N2C—C7C	125.5 (2)	C23C—C22C—C21C	119.3 (2)
C7C—N2C—C5C	122.4 (2)	O7C—C23C—C22C	123.8 (2)
C2C—N3C—C3C	123.7 (2)	O7C—C23C—C24C	115.7 (2)
O1C—C2C—N3C	122.4 (2)	C22C—C23C—C24C	120.5 (2)
O1C—C2C—C1C	120.8 (2)	O8C—C24C—C23C	122.4 (2)
N3C—C2C—C1C	116.8 (2)	O8C—C24C—C25C	117.9 (2)
N3C—C3C—C4C	112.7 (3)	C23C—C24C—C25C	119.8 (2)
O2C—C4C—C3C	109.1 (3)	O9C—C25C—C24C	121.6 (2)
O2C—C4C—C5C	105.01 (19)	O9C—C25C—C26C	118.7 (2)
C3C—C4C—C5C	113.0 (3)	C26C—C25C—C24C	119.8 (2)
N2C—C5C—C4C	102.1 (2)	C25C—C26C—C21C	119.9 (2)
O2C—C6C—N2C	110.0 (2)	O5D—C20D—O6D	122.2 (2)
O3C—C6C—O2C	121.5 (2)	O5D—C20D—C21D	120.1 (2)
O3C—C6C—N2C	128.5 (2)	O6D—C20D—C21D	117.7 (2)
C8C—C7C—N2C	121.0 (2)	C22D—C21D—C20D	117.8 (2)
C12C—C7C—N2C	120.4 (2)	C26D—C21D—C20D	121.7 (2)
C12C—C7C—C8C	118.5 (3)	C26D—C21D—C22D	120.5 (2)
C9C—C8C—C7C	119.4 (3)	C23D—C22D—C21D	119.7 (2)
F1C—C9C—C8C	117.1 (2)	O7D—C23D—C22D	124.5 (2)
F1C—C9C—C1OC	118.8 (2)	O7D—C23D—C24D	115.3 (2)
C8C—C9C—C1OC	124.1 (2)	C22D—C23D—C24D	120.2 (2)
C9C—C1OC—N1C	119.8 (2)	O8D—C24D—C23D	121.1 (2)
C9C—C1OC—C11C	115.3 (2)	O8D—C24D—C25D	118.7 (2)
C11C—C1OC—N1C	124.9 (2)	C23D—C24D—C25D	120.2 (2)
C12C—C11C—C1OC	121.8 (3)	O9D—C25D—C24D	121.6 (2)
C7C—C12C—C11C	120.8 (3)	O9D—C25D—C26D	118.9 (2)
N1C—C13C—C14C	110.2 (3)	C26D—C25D—C24D	119.6 (2)
O4C—C14C—C13C	110.6 (2)	C21D—C26D—C25D	119.8 (2)

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