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With the aim of improving the solubility of ciprofloxacin, polybasic organic acids were utilized to react with ciprofloxacin in different stoichiometric proportions. The use of the solvent drop grinding (SDG) method, as well as the solvent evaporation method, resulted in the crystalline salts ciprofloxacin/fumaric acid (1:1, 2:1), ciprofloxacin/maleic acid (1:1) and ciprofloxacin/citric acid (2:1). The solubilities of these salts in pure water (pH 7.0) were determined using high-performance liquid chromatography (HPLC) at 310 K, with the salts showing considerably greater solubility than ciprofloxacin itself and, interestingly, ciprofloxacin/fumaric acid (2:1) being more soluble than ciprofloxacin/fumaric acid (1:1). Intrigued by this phenomenon, we undertook a comparison of the crystal structures of the salts: the three-dimensional sandwich-like structure observed in the 2:1 salt indicates that the preferred stacking may be a factor in increasing the solubility of ciprofloxacin.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520615018582/ao5007sup1.cif
Contains datablocks 1, 2, 3, 4

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615018582/ao50071sup2.hkl
Contains datablock 1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615018582/ao50072sup3.hkl
Contains datablock 2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615018582/ao50073sup4.hkl
Contains datablock 3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520615018582/ao50074sup5.hkl
Contains datablock 4

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2052520615018582/ao5007sup6.pdf
Supporting figures

CCDC references: 1060662; 1060663; 1060664; 1060665

Computing details top

For all compounds, data collection: CrystalClear (Rigaku Inc., 2008); cell refinement: CrystalClear (Rigaku Inc., 2008); data reduction: CrystalClear (Rigaku Inc., 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII(Johnson,1976)andPLUTON(Spek,1990); software used to prepare material for publication: SHELXL97(Sheldrick, 1997).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
(1) top
Crystal data top
C17H19FN3O3·C4H3O4·H2OZ = 2
Mr = 465.43F(000) = 488
Triclinic, P1Dx = 1.474 Mg m3
a = 9.579 (3) ÅCu Kα radiation, λ = 1.54178 Å
b = 9.806 (2) ÅCell parameters from 3412 reflections
c = 11.612 (4) Åθ = 3.9–70.0°
α = 78.66 (2)°µ = 1.02 mm1
β = 89.44 (3)°T = 293 K
γ = 78.85 (4)°Prism, colorless
V = 1048.8 (5) Å30.72 × 0.23 × 0.19 mm
Data collection top
CCD
diffractometer
3866 independent reflections
Radiation source: fine-focus sealed tube3412 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.055
Detector resolution: 0 pixels mm-1θmax = 70.0°, θmin = 3.9°
ωκ scansh = 1111
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
k = 116
Tmin = 0.721, Tmax = 1.000l = 1413
15473 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.0826P)2 + 0.0488P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
3866 reflectionsΔρmax = 0.30 e Å3
323 parametersΔρmin = 0.22 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0103 (11)
Crystal data top
C17H19FN3O3·C4H3O4·H2Oγ = 78.85 (4)°
Mr = 465.43V = 1048.8 (5) Å3
Triclinic, P1Z = 2
a = 9.579 (3) ÅCu Kα radiation
b = 9.806 (2) ŵ = 1.02 mm1
c = 11.612 (4) ÅT = 293 K
α = 78.66 (2)°0.72 × 0.23 × 0.19 mm
β = 89.44 (3)°
Data collection top
CCD
diffractometer
3866 independent reflections
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
3412 reflections with I > 2σ(I)
Tmin = 0.721, Tmax = 1.000Rint = 0.055
15473 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.124H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.30 e Å3
3866 reflectionsΔρmin = 0.22 e Å3
323 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.19992 (14)0.47332 (13)0.37331 (10)0.0328 (3)
H1A0.26730.52840.34760.039*
C20.06799 (14)0.51155 (13)0.31929 (10)0.0335 (3)
C30.03972 (14)0.43085 (13)0.35557 (10)0.0334 (3)
C40.00154 (13)0.30974 (13)0.45142 (10)0.0310 (3)
C50.09558 (13)0.22261 (14)0.49555 (11)0.0339 (3)
H5A0.18660.24100.46180.041*
C60.05703 (13)0.11194 (14)0.58705 (11)0.0335 (3)
C70.07918 (13)0.07750 (13)0.64303 (10)0.0312 (3)
C80.17488 (13)0.16333 (13)0.59937 (10)0.0321 (3)
H8A0.26530.14500.63430.038*
C90.13834 (13)0.27704 (13)0.50387 (10)0.0300 (3)
C100.37955 (13)0.32797 (14)0.51529 (11)0.0352 (3)
H10A0.38670.35150.59300.042*
C110.47966 (15)0.19843 (16)0.49497 (13)0.0450 (3)
H11A0.44640.14190.44520.054*
H11B0.54370.14480.55930.054*
C120.50337 (15)0.34261 (17)0.43852 (15)0.0496 (4)
H12A0.58190.37600.46870.060*
H12B0.48460.37320.35450.060*
C130.04353 (15)0.63762 (14)0.22173 (11)0.0394 (3)
C140.02861 (14)0.05593 (14)0.83636 (11)0.0383 (3)
H14A0.07110.02310.81310.046*
H14B0.05330.00250.88840.046*
C150.05304 (14)0.20951 (14)0.89997 (11)0.0393 (3)
H15A0.00400.21780.96960.047*
H15B0.02380.26710.84910.047*
C160.29691 (14)0.24126 (14)0.82946 (12)0.0378 (3)
H16A0.27820.30160.77680.045*
H16B0.39640.26940.85440.045*
C170.26797 (13)0.08836 (14)0.76453 (12)0.0364 (3)
H17A0.29490.02850.81440.044*
H17B0.32440.07910.69460.044*
C180.31651 (14)0.36607 (14)0.06978 (12)0.0380 (3)
C190.31904 (14)0.21543 (14)0.05956 (12)0.0388 (3)
H19A0.28820.19920.01130.047*
C200.36202 (14)0.10492 (14)0.14431 (11)0.0370 (3)
H20A0.38780.11900.21740.044*
C210.37023 (14)0.04141 (14)0.12584 (11)0.0371 (3)
N10.23751 (11)0.36073 (11)0.46133 (9)0.0316 (3)
N20.11676 (11)0.04273 (11)0.73146 (9)0.0329 (3)
N30.20627 (12)0.26150 (12)0.93425 (9)0.0353 (3)
H3A0.2284 (18)0.2121 (19)0.9904 (16)0.047 (4)*
H3B0.229 (2)0.364 (2)0.9670 (18)0.062 (5)*
O10.13170 (12)0.70939 (11)0.19047 (9)0.0500 (3)
O20.08356 (13)0.66818 (13)0.16873 (10)0.0558 (3)
H2A0.133 (3)0.605 (3)0.205 (2)0.080 (7)*
O30.16330 (11)0.46215 (11)0.30945 (9)0.0462 (3)
O40.28813 (14)0.45614 (11)0.02439 (10)0.0589 (3)
O50.34710 (13)0.39136 (11)0.16600 (10)0.0535 (3)
O60.31810 (14)0.06803 (11)0.04040 (10)0.0569 (3)
O70.44040 (14)0.13874 (12)0.21017 (10)0.0558 (3)
H7A0.449 (3)0.235 (3)0.197 (2)0.085 (7)*
O80.48705 (17)0.39452 (13)0.17796 (13)0.0669 (4)
H8B0.429 (3)0.455 (3)0.165 (2)0.085 (7)*
H8C0.565 (3)0.414 (3)0.135 (2)0.086 (7)*
F10.15187 (8)0.02741 (9)0.62348 (7)0.0470 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0373 (7)0.0317 (6)0.0267 (6)0.0054 (5)0.0024 (5)0.0007 (4)
C20.0382 (7)0.0335 (7)0.0247 (6)0.0018 (5)0.0007 (5)0.0005 (5)
C30.0354 (6)0.0359 (7)0.0257 (6)0.0015 (5)0.0046 (5)0.0039 (5)
C40.0320 (6)0.0337 (7)0.0244 (6)0.0024 (5)0.0021 (5)0.0024 (5)
C50.0288 (6)0.0397 (7)0.0303 (6)0.0040 (5)0.0043 (5)0.0023 (5)
C60.0295 (6)0.0384 (7)0.0313 (6)0.0087 (5)0.0012 (5)0.0015 (5)
C70.0317 (6)0.0332 (6)0.0251 (6)0.0029 (5)0.0002 (5)0.0006 (4)
C80.0291 (6)0.0375 (7)0.0263 (6)0.0049 (5)0.0026 (4)0.0002 (5)
C90.0302 (6)0.0335 (6)0.0245 (6)0.0048 (5)0.0002 (4)0.0027 (4)
C100.0315 (6)0.0390 (7)0.0327 (6)0.0079 (5)0.0041 (5)0.0001 (5)
C110.0370 (7)0.0439 (8)0.0474 (8)0.0009 (6)0.0037 (6)0.0007 (6)
C120.0320 (7)0.0539 (9)0.0549 (9)0.0071 (6)0.0037 (6)0.0072 (6)
C130.0482 (8)0.0367 (7)0.0280 (6)0.0021 (6)0.0017 (5)0.0002 (5)
C140.0376 (7)0.0413 (7)0.0288 (6)0.0013 (5)0.0051 (5)0.0038 (5)
C150.0387 (7)0.0429 (8)0.0317 (6)0.0088 (5)0.0021 (5)0.0044 (5)
C160.0336 (6)0.0370 (7)0.0372 (7)0.0024 (5)0.0029 (5)0.0022 (5)
C170.0293 (6)0.0385 (7)0.0357 (6)0.0054 (5)0.0022 (5)0.0055 (5)
C180.0338 (6)0.0325 (7)0.0453 (7)0.0040 (5)0.0024 (5)0.0046 (5)
C190.0403 (7)0.0352 (7)0.0392 (7)0.0076 (5)0.0062 (5)0.0027 (5)
C200.0394 (7)0.0365 (7)0.0342 (6)0.0070 (5)0.0050 (5)0.0048 (5)
C210.0424 (7)0.0345 (7)0.0328 (6)0.0092 (5)0.0028 (5)0.0010 (5)
N10.0300 (5)0.0346 (6)0.0270 (5)0.0057 (4)0.0015 (4)0.0013 (4)
N20.0289 (5)0.0371 (6)0.0269 (5)0.0034 (4)0.0007 (4)0.0045 (4)
N30.0437 (6)0.0311 (6)0.0281 (5)0.0067 (4)0.0052 (4)0.0016 (4)
O10.0570 (6)0.0431 (6)0.0428 (6)0.0109 (5)0.0008 (5)0.0096 (4)
O20.0585 (7)0.0526 (7)0.0455 (6)0.0107 (5)0.0183 (5)0.0170 (5)
O30.0399 (5)0.0483 (6)0.0428 (5)0.0056 (4)0.0154 (4)0.0071 (4)
O40.0821 (8)0.0336 (6)0.0541 (6)0.0061 (5)0.0073 (6)0.0035 (4)
O50.0688 (7)0.0417 (6)0.0505 (6)0.0076 (5)0.0001 (5)0.0132 (4)
O60.0856 (9)0.0418 (6)0.0450 (6)0.0200 (5)0.0212 (5)0.0037 (4)
O70.0826 (8)0.0339 (6)0.0447 (6)0.0016 (5)0.0205 (5)0.0015 (4)
O80.0744 (9)0.0398 (6)0.0884 (9)0.0129 (6)0.0200 (7)0.0162 (6)
F10.0363 (4)0.0540 (5)0.0467 (5)0.0180 (3)0.0027 (3)0.0086 (4)
Geometric parameters (Å, º) top
C1—N11.3428 (16)C14—N21.4743 (15)
C1—C21.3678 (19)C14—C151.5158 (18)
C1—H1A0.9300C14—H14A0.9700
C2—C31.430 (2)C14—H14B0.9700
C2—C131.4862 (17)C15—N31.4882 (18)
C3—O31.2609 (17)C15—H15A0.9700
C3—C41.4535 (17)C15—H15B0.9700
C4—C91.4025 (18)C16—N31.4917 (17)
C4—C51.4085 (19)C16—C171.5140 (18)
C5—C61.3573 (18)C16—H16A0.9700
C5—H5A0.9300C16—H16B0.9700
C6—F11.3554 (15)C17—N21.4623 (16)
C6—C71.4138 (19)C17—H17A0.9700
C7—C81.3883 (18)C17—H17B0.9700
C7—N21.3932 (16)C18—O51.2406 (18)
C8—C91.4021 (17)C18—O41.2581 (18)
C8—H8A0.9300C18—C191.5006 (19)
C9—N11.3974 (17)C19—C201.315 (2)
C10—N11.4545 (17)C19—H19A0.9300
C10—C121.4890 (19)C20—C211.4793 (19)
C10—C111.494 (2)C20—H20A0.9300
C10—H10A0.9800C21—O61.2099 (18)
C11—C121.496 (2)C21—O71.3109 (17)
C11—H11A0.9700N3—H3A0.933 (19)
C11—H11B0.9700N3—H3B0.99 (2)
C12—H12A0.9700O2—H2A0.89 (2)
C12—H12B0.9700O7—H7A0.97 (3)
C13—O11.2099 (19)O8—H8B0.92 (3)
C13—O21.3235 (19)O8—H8C0.91 (3)
N1—C1—C2123.64 (12)C15—C14—H14A109.7
N1—C1—H1A118.2N2—C14—H14B109.7
C2—C1—H1A118.2C15—C14—H14B109.7
C1—C2—C3120.45 (11)H14A—C14—H14B108.2
C1—C2—C13117.24 (12)N3—C15—C14110.08 (12)
C3—C2—C13122.30 (12)N3—C15—H15A109.6
O3—C3—C2123.01 (12)C14—C15—H15A109.6
O3—C3—C4121.44 (12)N3—C15—H15B109.6
C2—C3—C4115.55 (11)C14—C15—H15B109.6
C9—C4—C5117.93 (11)H15A—C15—H15B108.2
C9—C4—C3121.18 (12)N3—C16—C17111.41 (11)
C5—C4—C3120.88 (12)N3—C16—H16A109.3
C6—C5—C4120.37 (12)C17—C16—H16A109.3
C6—C5—H5A119.8N3—C16—H16B109.3
C4—C5—H5A119.8C17—C16—H16B109.3
F1—C6—C5118.35 (11)H16A—C16—H16B108.0
F1—C6—C7118.51 (11)N2—C17—C16109.81 (11)
C5—C6—C7123.09 (12)N2—C17—H17A109.7
C8—C7—N2122.47 (11)C16—C17—H17A109.7
C8—C7—C6116.49 (11)N2—C17—H17B109.7
N2—C7—C6120.88 (12)C16—C17—H17B109.7
C7—C8—C9121.52 (12)H17A—C17—H17B108.2
C7—C8—H8A119.2O5—C18—O4125.70 (13)
C9—C8—H8A119.2O5—C18—C19119.07 (12)
N1—C9—C8120.14 (11)O4—C18—C19115.16 (13)
N1—C9—C4119.28 (11)C20—C19—C18124.26 (13)
C8—C9—C4120.57 (12)C20—C19—H19A117.9
N1—C10—C12118.78 (11)C18—C19—H19A117.9
N1—C10—C11118.37 (12)C19—C20—C21121.41 (12)
C12—C10—C1160.19 (10)C19—C20—H20A119.3
N1—C10—H10A116.0C21—C20—H20A119.3
C12—C10—H10A116.0O6—C21—O7123.49 (13)
C11—C10—H10A116.0O6—C21—C20122.97 (12)
C10—C11—C1259.75 (10)O7—C21—C20113.54 (12)
C10—C11—H11A117.8C1—N1—C9119.88 (11)
C12—C11—H11A117.8C1—N1—C10120.37 (11)
C10—C11—H11B117.8C9—N1—C10119.72 (10)
C12—C11—H11B117.8C7—N2—C17116.80 (10)
H11A—C11—H11B114.9C7—N2—C14118.19 (10)
C10—C12—C1160.06 (10)C17—N2—C14110.74 (10)
C10—C12—H12A117.8C15—N3—C16110.65 (10)
C11—C12—H12A117.8C15—N3—H3A107.7 (11)
C10—C12—H12B117.8C16—N3—H3A111.5 (11)
C11—C12—H12B117.8C15—N3—H3B112.7 (12)
H12A—C12—H12B114.9C16—N3—H3B104.9 (11)
O1—C13—O2120.72 (12)H3A—N3—H3B109.4 (16)
O1—C13—C2123.78 (13)C13—O2—H2A107.4 (16)
O2—C13—C2115.50 (13)C21—O7—H7A113.6 (15)
N2—C14—C15109.73 (11)H8B—O8—H8C106 (2)
N2—C14—H14A109.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O6i0.933 (19)1.968 (19)2.8280 (18)152.3 (15)
N3—H3A···O1ii0.933 (19)2.526 (18)3.0244 (18)113.7 (13)
N3—H3B···O4ii0.99 (2)1.73 (2)2.6752 (17)160.2 (18)
O2—H2A···O30.89 (2)1.73 (3)2.5708 (17)156 (2)
O7—H7A···O80.97 (3)1.60 (3)2.5618 (17)172 (2)
O8—H8B···O5iii0.92 (3)1.83 (3)2.726 (2)165 (2)
O8—H8C···O4iv0.91 (3)1.93 (3)2.833 (2)171 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y1, z+1; (iii) x, y1, z; (iv) x+1, y, z.
(2) top
Crystal data top
2(C17H19FN3O3)·C4H2O4·3(H2O)Z = 4
Mr = 832.81F(000) = 1752
Monoclinic, P21/nDx = 1.450 Mg m3
a = 9.922 (4) ÅCu Kα radiation, λ = 1.54178 Å
b = 30.199 (9) ŵ = 0.99 mm1
c = 13.528 (8) ÅT = 293 K
β = 109.717 (13)°Prism, colorless
V = 3816 (3) Å30.43 × 0.12 × 0.03 mm
Data collection top
CCD
diffractometer
7316 independent reflections
Radiation source: fine-focus sealed tube5695 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.125
Detector resolution: 0 pixels mm-1θmax = 72.4°, θmin = 3.8°
ωκ scansh = 1112
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
k = 3736
Tmin = 0.676, Tmax = 0.971l = 1315
36407 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.082Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.249H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.1422P)2 + 0.8915P]
where P = (Fo2 + 2Fc2)/3
7316 reflections(Δ/σ)max < 0.001
588 parametersΔρmax = 0.41 e Å3
14 restraintsΔρmin = 0.56 e Å3
Crystal data top
2(C17H19FN3O3)·C4H2O4·3(H2O)V = 3816 (3) Å3
Mr = 832.81Z = 4
Monoclinic, P21/nCu Kα radiation
a = 9.922 (4) ŵ = 0.99 mm1
b = 30.199 (9) ÅT = 293 K
c = 13.528 (8) Å0.43 × 0.12 × 0.03 mm
β = 109.717 (13)°
Data collection top
CCD
diffractometer
7316 independent reflections
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
5695 reflections with I > 2σ(I)
Tmin = 0.676, Tmax = 0.971Rint = 0.125
36407 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.08214 restraints
wR(F2) = 0.249H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.41 e Å3
7316 reflectionsΔρmin = 0.56 e Å3
588 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.06277 (18)0.03015 (7)0.76900 (19)0.0692 (6)
F1B0.93352 (17)0.06347 (6)0.73563 (16)0.0582 (5)
N1A0.6455 (2)0.05550 (7)0.91567 (17)0.0364 (5)
N1B0.3545 (2)0.02830 (7)0.58599 (17)0.0376 (5)
N2A0.1665 (2)0.11701 (8)0.80425 (19)0.0449 (6)
N2B0.7454 (3)0.13390 (8)0.6904 (2)0.0515 (6)
N3A0.0309 (2)0.18566 (8)0.80108 (19)0.0421 (5)
H3A0.019 (4)0.2019 (12)0.751 (2)0.066 (11)*
H3B0.094 (3)0.1965 (12)0.827 (3)0.059 (10)*
N3B0.8751 (3)0.21502 (9)0.7765 (2)0.0481 (6)
H3C0.935 (3)0.2291 (11)0.830 (2)0.058 (10)*
H3D0.854 (4)0.2346 (11)0.725 (2)0.072 (12)*
O1A0.9192 (3)0.05331 (10)0.9912 (3)0.0820 (9)
O1B0.2081 (2)0.10119 (7)0.56285 (19)0.0550 (6)
O2A0.7381 (3)0.09969 (8)0.9308 (2)0.0629 (6)
H2A0.641 (5)0.0973 (16)0.895 (4)0.084 (14)*
O2B0.4272 (3)0.12816 (7)0.6044 (2)0.0584 (6)
H2B0.513 (7)0.1198 (19)0.626 (5)0.112 (19)*
O3A0.4852 (2)0.07065 (6)0.86188 (17)0.0500 (5)
O3B0.6403 (2)0.07508 (7)0.66058 (18)0.0496 (5)
O40.3596 (3)0.27285 (14)1.0048 (2)0.0968 (11)
O50.5356 (2)0.26466 (9)1.15531 (17)0.0589 (6)
O60.9484 (2)0.23494 (9)1.02436 (17)0.0571 (6)
O70.7613 (2)0.22358 (7)0.88089 (15)0.0455 (5)
O8A0.1701 (4)0.30257 (19)1.0970 (5)0.079 (2)0.823 (18)
H8A0.208 (7)0.2988 (19)1.046 (4)0.17 (3)*
H8B0.087 (3)0.2991 (14)1.046 (3)0.086 (14)*
O8B0.148 (2)0.3217 (8)1.0450 (19)0.069 (7)*0.177 (18)
O90.4790 (5)0.19571 (17)0.7609 (4)0.1203 (14)
H9A0.428 (7)0.1769 (19)0.705 (4)0.144*
H9B0.579 (3)0.198 (2)0.801 (5)0.144*
O10A1.304 (3)0.1979 (4)0.7053 (7)0.126 (5)0.64 (5)
H10C1.254 (14)0.207 (6)0.640 (3)0.44 (12)*
H10D1.327 (6)0.2268 (13)0.718 (14)0.33 (9)*
O10B1.249 (3)0.2095 (9)0.7047 (12)0.096 (6)*0.36 (5)
C1A0.7325 (3)0.02005 (9)0.9353 (2)0.0408 (6)
H1AA0.83080.02500.95990.049*
C1B0.3109 (3)0.01383 (9)0.5766 (2)0.0395 (6)
H1BA0.21290.01910.55100.047*
C2A0.6853 (3)0.02282 (9)0.9212 (2)0.0397 (6)
C2B0.4005 (3)0.04985 (9)0.6019 (2)0.0371 (6)
C3A0.5342 (3)0.03169 (9)0.87993 (19)0.0373 (6)
C3B0.5521 (3)0.04306 (9)0.63788 (19)0.0367 (6)
C4A0.4423 (3)0.00647 (9)0.85890 (19)0.0355 (5)
C4B0.5996 (3)0.00223 (9)0.64732 (19)0.0345 (5)
C5A0.2922 (3)0.00134 (9)0.8201 (2)0.0399 (6)
H5AA0.25220.02680.80750.048*
C5B0.7467 (3)0.01228 (9)0.6834 (2)0.0389 (6)
H5BA0.81390.01050.70020.047*
C6A0.2066 (3)0.03727 (10)0.8012 (2)0.0414 (6)
C6B0.7904 (3)0.05487 (10)0.6937 (2)0.0400 (6)
C7A0.2572 (3)0.08122 (9)0.8169 (2)0.0369 (6)
C7B0.6959 (3)0.09141 (9)0.6695 (2)0.0388 (6)
C8A0.4060 (3)0.08614 (9)0.8537 (2)0.0362 (5)
H8AA0.44530.11440.86340.043*
C8B0.5492 (3)0.08135 (9)0.6317 (2)0.0406 (6)
H8BA0.48270.10420.61260.049*
C9A0.4968 (3)0.04942 (8)0.87611 (19)0.0333 (5)
C9B0.5019 (3)0.03771 (9)0.62223 (19)0.0351 (5)
C10A0.7035 (3)0.10004 (9)0.9300 (2)0.0432 (6)
H10A0.69340.11620.86510.052*
C10B0.2502 (3)0.06376 (11)0.5482 (3)0.0501 (7)
H10B0.24450.07640.48010.060*
C11A0.6918 (3)0.12754 (10)1.0181 (3)0.0533 (8)
H11A0.67260.15891.00540.064*
H11B0.64900.11411.06560.064*
C11B0.2245 (4)0.09553 (13)0.6235 (3)0.0630 (9)
H11C0.27660.09120.69760.076*
H11D0.20640.12620.60180.076*
C12A0.8332 (3)0.11065 (11)1.0201 (3)0.0536 (7)
H12C0.90020.13181.00880.064*
H12D0.87670.08701.06900.064*
C12B0.1133 (3)0.06182 (12)0.5683 (3)0.0592 (8)
H12A0.02800.07220.51350.071*
H12B0.09810.03720.60930.071*
C13A0.7912 (4)0.05929 (11)0.9503 (3)0.0527 (7)
C13B0.3362 (3)0.09469 (10)0.5879 (2)0.0421 (6)
C14A0.0305 (3)0.12070 (11)0.7179 (2)0.0457 (7)
H14A0.00120.09160.68940.055*
H14B0.04290.13880.66240.055*
C14B0.8649 (3)0.15152 (10)0.6607 (3)0.0494 (7)
H14C0.91960.12720.64640.059*
H14D0.82760.16920.59730.059*
C15A0.0805 (3)0.14129 (10)0.7568 (2)0.0471 (7)
H15A0.17060.14400.69930.057*
H15B0.09600.12260.81030.057*
C15B0.9600 (3)0.17946 (11)0.7478 (3)0.0518 (7)
H15C1.03430.19280.72580.062*
H15D1.00570.16100.80860.062*
C16A0.1110 (3)0.18288 (10)0.8865 (2)0.0430 (6)
H16A0.10110.16650.94540.052*
H16B0.14430.21250.91070.052*
C16B0.7485 (3)0.19724 (11)0.7989 (3)0.0507 (7)
H16C0.78050.17970.86260.061*
H16D0.69180.22160.81020.061*
C17A0.2196 (3)0.16009 (10)0.8477 (2)0.0452 (6)
H17A0.23780.17820.79420.054*
H17B0.30910.15660.90530.054*
C17B0.6572 (3)0.16899 (11)0.7092 (3)0.0536 (7)
H17C0.61820.18690.64650.064*
H17D0.57810.15640.72660.064*
C180.4855 (3)0.26345 (11)1.0572 (2)0.0494 (7)
C190.5794 (3)0.24896 (10)0.9978 (2)0.0433 (6)
H19A0.53550.23910.92930.052*
C200.7206 (3)0.24908 (10)1.0354 (2)0.0423 (6)
H20A0.76430.25871.10420.051*
C210.8157 (3)0.23493 (9)0.9759 (2)0.0370 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0270 (8)0.0679 (12)0.1077 (17)0.0081 (8)0.0164 (9)0.0033 (11)
F1B0.0281 (8)0.0658 (11)0.0788 (12)0.0075 (7)0.0157 (8)0.0035 (9)
N1A0.0266 (10)0.0428 (12)0.0438 (11)0.0039 (9)0.0171 (9)0.0021 (9)
N1B0.0282 (10)0.0453 (12)0.0440 (12)0.0031 (9)0.0184 (9)0.0002 (9)
N2A0.0291 (11)0.0494 (13)0.0550 (13)0.0053 (10)0.0125 (10)0.0095 (10)
N2B0.0445 (13)0.0504 (14)0.0729 (17)0.0089 (11)0.0374 (13)0.0127 (12)
N3A0.0354 (12)0.0533 (13)0.0474 (13)0.0073 (10)0.0266 (10)0.0060 (10)
N3B0.0467 (14)0.0501 (14)0.0437 (13)0.0078 (11)0.0101 (11)0.0015 (11)
O1A0.0455 (14)0.0778 (17)0.123 (2)0.0236 (13)0.0291 (15)0.0061 (16)
O1B0.0397 (11)0.0578 (12)0.0710 (14)0.0084 (9)0.0232 (10)0.0034 (10)
O2A0.0723 (17)0.0516 (13)0.0682 (15)0.0193 (12)0.0280 (13)0.0033 (10)
O2B0.0461 (13)0.0450 (11)0.0874 (17)0.0044 (10)0.0268 (12)0.0035 (11)
O3A0.0587 (13)0.0401 (10)0.0544 (12)0.0000 (9)0.0233 (10)0.0015 (8)
O3B0.0371 (10)0.0478 (11)0.0659 (13)0.0082 (9)0.0200 (9)0.0059 (9)
O40.0453 (14)0.182 (3)0.0642 (16)0.0328 (18)0.0202 (12)0.0173 (18)
O50.0514 (12)0.0840 (16)0.0499 (12)0.0084 (11)0.0284 (10)0.0100 (10)
O60.0314 (10)0.0900 (16)0.0507 (12)0.0058 (10)0.0149 (9)0.0005 (10)
O70.0389 (10)0.0634 (12)0.0393 (10)0.0067 (9)0.0198 (8)0.0006 (8)
O8A0.055 (2)0.097 (4)0.092 (4)0.0117 (19)0.034 (2)0.029 (3)
O90.090 (3)0.147 (4)0.129 (3)0.025 (2)0.043 (2)0.035 (3)
O10A0.137 (10)0.095 (5)0.115 (5)0.020 (6)0.001 (5)0.020 (4)
C1A0.0339 (13)0.0501 (15)0.0447 (14)0.0079 (11)0.0214 (11)0.0030 (11)
C1B0.0325 (13)0.0502 (15)0.0411 (13)0.0030 (11)0.0193 (10)0.0020 (11)
C2A0.0407 (14)0.0467 (15)0.0375 (13)0.0102 (12)0.0209 (11)0.0020 (10)
C2B0.0333 (13)0.0487 (15)0.0348 (12)0.0013 (11)0.0186 (10)0.0006 (10)
C3A0.0439 (14)0.0436 (14)0.0321 (12)0.0042 (11)0.0229 (11)0.0009 (10)
C3B0.0336 (13)0.0477 (14)0.0340 (12)0.0039 (11)0.0184 (10)0.0022 (10)
C4A0.0363 (13)0.0422 (13)0.0337 (12)0.0017 (11)0.0193 (10)0.0003 (10)
C4B0.0310 (12)0.0465 (14)0.0319 (12)0.0005 (10)0.0183 (10)0.0000 (10)
C5A0.0369 (13)0.0434 (14)0.0440 (14)0.0050 (11)0.0197 (11)0.0044 (11)
C5B0.0288 (12)0.0509 (15)0.0407 (13)0.0040 (11)0.0167 (10)0.0015 (11)
C6A0.0258 (12)0.0528 (15)0.0483 (15)0.0050 (11)0.0161 (11)0.0032 (12)
C6B0.0255 (12)0.0541 (15)0.0447 (14)0.0049 (11)0.0174 (10)0.0041 (11)
C7A0.0274 (12)0.0488 (14)0.0380 (13)0.0028 (11)0.0156 (10)0.0034 (10)
C7B0.0347 (13)0.0469 (14)0.0418 (13)0.0056 (11)0.0221 (11)0.0033 (11)
C8A0.0292 (12)0.0413 (13)0.0431 (13)0.0003 (10)0.0188 (10)0.0001 (10)
C8B0.0364 (13)0.0457 (14)0.0443 (14)0.0018 (11)0.0197 (11)0.0001 (11)
C9A0.0279 (12)0.0427 (13)0.0347 (12)0.0003 (10)0.0178 (9)0.0004 (10)
C9B0.0295 (12)0.0468 (14)0.0342 (12)0.0003 (10)0.0174 (10)0.0001 (10)
C10A0.0323 (13)0.0461 (14)0.0569 (16)0.0026 (11)0.0226 (12)0.0031 (12)
C10B0.0347 (14)0.0562 (17)0.0626 (18)0.0076 (13)0.0208 (13)0.0064 (14)
C11A0.0447 (16)0.0471 (15)0.078 (2)0.0051 (13)0.0340 (15)0.0081 (14)
C11B0.0557 (19)0.066 (2)0.073 (2)0.0101 (16)0.0290 (17)0.0055 (16)
C12A0.0390 (15)0.0593 (18)0.0658 (19)0.0035 (13)0.0218 (14)0.0081 (14)
C12B0.0364 (15)0.066 (2)0.078 (2)0.0054 (14)0.0225 (15)0.0003 (16)
C13A0.0547 (18)0.0531 (18)0.0574 (18)0.0181 (15)0.0280 (15)0.0013 (13)
C13B0.0397 (14)0.0502 (15)0.0432 (14)0.0054 (12)0.0228 (11)0.0003 (11)
C14A0.0321 (13)0.0587 (17)0.0447 (14)0.0079 (12)0.0107 (11)0.0046 (12)
C14B0.0426 (15)0.0527 (16)0.0625 (18)0.0084 (13)0.0304 (14)0.0030 (13)
C15A0.0302 (12)0.0582 (17)0.0552 (16)0.0036 (12)0.0174 (12)0.0022 (13)
C15B0.0367 (14)0.0596 (18)0.0591 (17)0.0040 (13)0.0161 (13)0.0038 (14)
C16A0.0361 (13)0.0506 (15)0.0468 (14)0.0035 (12)0.0200 (12)0.0018 (12)
C16B0.0526 (17)0.0524 (16)0.0553 (17)0.0021 (13)0.0290 (14)0.0016 (13)
C17A0.0322 (13)0.0478 (15)0.0585 (17)0.0010 (12)0.0192 (12)0.0053 (12)
C17B0.0429 (16)0.0528 (17)0.072 (2)0.0039 (13)0.0290 (15)0.0098 (15)
C180.0398 (15)0.0657 (18)0.0488 (16)0.0024 (13)0.0228 (13)0.0068 (13)
C190.0362 (14)0.0554 (16)0.0434 (14)0.0035 (12)0.0201 (11)0.0018 (12)
C200.0379 (14)0.0529 (15)0.0423 (13)0.0026 (12)0.0214 (11)0.0037 (11)
C210.0312 (12)0.0431 (13)0.0400 (13)0.0054 (10)0.0164 (10)0.0056 (10)
Geometric parameters (Å, º) top
F1A—C6A1.361 (3)C4B—C5B1.407 (4)
F1B—C6B1.364 (3)C4B—C9B1.408 (4)
N1A—C1A1.344 (3)C5A—C6A1.348 (4)
N1A—C9A1.401 (3)C5A—H5AA0.9300
N1A—C10A1.450 (4)C5B—C6B1.350 (4)
N1B—C1B1.336 (4)C5B—H5BA0.9300
N1B—C9B1.405 (3)C6A—C7A1.409 (4)
N1B—C10B1.457 (4)C6B—C7B1.413 (4)
N2A—C7A1.379 (3)C7A—C8A1.398 (4)
N2A—C17A1.451 (4)C7B—C8B1.403 (4)
N2A—C14A1.461 (3)C8A—C9A1.396 (4)
N2B—C7B1.369 (4)C8A—H8AA0.9300
N2B—C17B1.450 (4)C8B—C9B1.391 (4)
N2B—C14B1.474 (4)C8B—H8BA0.9300
N3A—C15A1.483 (4)C10A—C12A1.478 (4)
N3A—C16A1.492 (4)C10A—C11A1.489 (5)
N3A—H3A0.873 (19)C10A—H10A0.9800
N3A—H3B0.872 (19)C10B—C12B1.475 (4)
N3B—C16B1.489 (4)C10B—C11B1.483 (5)
N3B—C15B1.495 (4)C10B—H10B0.9800
N3B—H3C0.880 (19)C11A—C12A1.485 (4)
N3B—H3D0.886 (19)C11A—H11A0.9700
O1A—C13A1.215 (4)C11A—H11B0.9700
O1B—C13B1.215 (3)C11B—C12B1.502 (5)
O2A—C13A1.320 (4)C11B—H11C0.9700
O2A—H2A0.93 (5)C11B—H11D0.9700
O2B—C13B1.323 (4)C12A—H12C0.9700
O2B—H2B0.84 (6)C12A—H12D0.9700
O3A—C3A1.265 (3)C12B—H12A0.9700
O3B—C3B1.270 (3)C12B—H12B0.9700
O4—C181.244 (4)C14A—C15A1.506 (4)
O5—C181.250 (4)C14A—H14A0.9700
O6—C211.257 (3)C14A—H14B0.9700
O7—C211.262 (3)C14B—C15B1.497 (4)
O8A—H8A0.89 (2)C14B—H14C0.9700
O8A—H8B0.888 (19)C14B—H14D0.9700
O8B—H8A0.91 (2)C15A—H15A0.9700
O8B—H8B0.913 (19)C15A—H15B0.9700
O9—H9A0.95 (2)C15B—H15C0.9700
O9—H9B0.95 (2)C15B—H15D0.9700
O10A—H10C0.90 (2)C16A—C17A1.515 (4)
O10A—H10D0.90 (2)C16A—H16A0.9700
O10B—H10C0.90 (2)C16A—H16B0.9700
O10B—H10D0.90 (2)C16B—C17B1.510 (5)
C1A—C2A1.368 (4)C16B—H16C0.9700
C1A—H1AA0.9300C16B—H16D0.9700
C1B—C2B1.373 (4)C17A—H17A0.9700
C1B—H1BA0.9300C17A—H17B0.9700
C2A—C3A1.438 (4)C17B—H17C0.9700
C2A—C13A1.481 (4)C17B—H17D0.9700
C2B—C3B1.431 (4)C18—C191.487 (4)
C2B—C13B1.482 (4)C19—C201.320 (4)
C3A—C4A1.437 (4)C19—H19A0.9300
C3B—C4B1.438 (4)C20—C211.495 (4)
C4A—C9A1.394 (4)C20—H20A0.9300
C4A—C5A1.411 (4)
C1A—N1A—C9A119.6 (2)N1B—C10B—H10B115.1
C1A—N1A—C10A120.9 (2)C12B—C10B—H10B115.1
C9A—N1A—C10A119.4 (2)C11B—C10B—H10B115.1
C1B—N1B—C9B119.4 (2)C12A—C11A—C10A59.6 (2)
C1B—N1B—C10B119.9 (2)C12A—C11A—H11A117.8
C9B—N1B—C10B120.4 (2)C10A—C11A—H11A117.8
C7A—N2A—C17A121.3 (2)C12A—C11A—H11B117.8
C7A—N2A—C14A123.2 (2)C10A—C11A—H11B117.8
C17A—N2A—C14A111.5 (2)H11A—C11A—H11B114.9
C7B—N2B—C17B121.7 (2)C10B—C11B—C12B59.2 (2)
C7B—N2B—C14B123.2 (2)C10B—C11B—H11C117.9
C17B—N2B—C14B111.9 (2)C12B—C11B—H11C117.9
C15A—N3A—C16A111.1 (2)C10B—C11B—H11D117.9
C15A—N3A—H3A108 (3)C12B—C11B—H11D117.9
C16A—N3A—H3A107 (3)H11C—C11B—H11D115.0
C15A—N3A—H3B108 (2)C10A—C12A—C11A60.3 (2)
C16A—N3A—H3B109 (2)C10A—C12A—H12C117.7
H3A—N3A—H3B113 (4)C11A—C12A—H12C117.7
C16B—N3B—C15B112.4 (2)C10A—C12A—H12D117.7
C16B—N3B—H3C113 (2)C11A—C12A—H12D117.7
C15B—N3B—H3C106 (2)H12C—C12A—H12D114.9
C16B—N3B—H3D114 (3)C10B—C12B—C11B59.7 (2)
C15B—N3B—H3D106 (3)C10B—C12B—H12A117.8
H3C—N3B—H3D104 (4)C11B—C12B—H12A117.8
C13A—O2A—H2A108 (3)C10B—C12B—H12B117.8
C13B—O2B—H2B113 (4)C11B—C12B—H12B117.8
H8A—O8A—H8B84 (5)H12A—C12B—H12B114.9
H8A—O8B—H8B82 (5)O1A—C13A—O2A120.9 (3)
H9A—O9—H9B131 (6)O1A—C13A—C2A123.3 (3)
H10C—O10A—H10D85 (10)O2A—C13A—C2A115.8 (3)
H10C—O10B—H10D85 (10)O1B—C13B—O2B120.9 (3)
N1A—C1A—C2A124.0 (3)O1B—C13B—C2B123.2 (3)
N1A—C1A—H1AA118.0O2B—C13B—C2B115.9 (2)
C2A—C1A—H1AA118.0N2A—C14A—C15A109.9 (2)
N1B—C1B—C2B124.7 (2)N2A—C14A—H14A109.7
N1B—C1B—H1BA117.6C15A—C14A—H14A109.7
C2B—C1B—H1BA117.6N2A—C14A—H14B109.7
C1A—C2A—C3A119.6 (2)C15A—C14A—H14B109.7
C1A—C2A—C13A119.2 (3)H14A—C14A—H14B108.2
C3A—C2A—C13A121.2 (3)N2B—C14B—C15B109.9 (3)
C1B—C2B—C3B119.3 (2)N2B—C14B—H14C109.7
C1B—C2B—C13B118.5 (2)C15B—C14B—H14C109.7
C3B—C2B—C13B122.2 (2)N2B—C14B—H14D109.7
O3A—C3A—C4A122.1 (3)C15B—C14B—H14D109.7
O3A—C3A—C2A122.1 (2)H14C—C14B—H14D108.2
C4A—C3A—C2A115.9 (2)N3A—C15A—C14A109.4 (2)
O3B—C3B—C2B122.1 (2)N3A—C15A—H15A109.8
O3B—C3B—C4B121.6 (2)C14A—C15A—H15A109.8
C2B—C3B—C4B116.2 (2)N3A—C15A—H15B109.8
C9A—C4A—C5A117.8 (2)C14A—C15A—H15B109.8
C9A—C4A—C3A121.9 (2)H15A—C15A—H15B108.2
C5A—C4A—C3A120.3 (2)N3B—C15B—C14B110.4 (2)
C5B—C4B—C9B118.0 (2)N3B—C15B—H15C109.6
C5B—C4B—C3B120.4 (2)C14B—C15B—H15C109.6
C9B—C4B—C3B121.6 (2)N3B—C15B—H15D109.6
C6A—C5A—C4A120.0 (2)C14B—C15B—H15D109.6
C6A—C5A—H5AA120.0H15C—C15B—H15D108.1
C4A—C5A—H5AA120.0N3A—C16A—C17A110.6 (2)
C6B—C5B—C4B120.1 (2)N3A—C16A—H16A109.5
C6B—C5B—H5BA120.0C17A—C16A—H16A109.5
C4B—C5B—H5BA120.0N3A—C16A—H16B109.5
C5A—C6A—F1A117.3 (2)C17A—C16A—H16B109.5
C5A—C6A—C7A124.1 (2)H16A—C16A—H16B108.1
F1A—C6A—C7A118.6 (2)N3B—C16B—C17B111.0 (3)
C5B—C6B—F1B118.5 (2)N3B—C16B—H16C109.4
C5B—C6B—C7B123.7 (2)C17B—C16B—H16C109.4
F1B—C6B—C7B117.6 (2)N3B—C16B—H16D109.4
N2A—C7A—C8A121.8 (2)C17B—C16B—H16D109.4
N2A—C7A—C6A122.4 (2)H16C—C16B—H16D108.0
C8A—C7A—C6A115.7 (2)N2A—C17A—C16A110.1 (2)
N2B—C7B—C8B122.3 (3)N2A—C17A—H17A109.6
N2B—C7B—C6B121.3 (2)C16A—C17A—H17A109.6
C8B—C7B—C6B116.2 (2)N2A—C17A—H17B109.6
C9A—C8A—C7A121.3 (2)C16A—C17A—H17B109.6
C9A—C8A—H8AA119.4H17A—C17A—H17B108.1
C7A—C8A—H8AA119.4N2B—C17B—C16B108.6 (3)
C9B—C8B—C7B121.0 (2)N2B—C17B—H17C110.0
C9B—C8B—H8BA119.5C16B—C17B—H17C110.0
C7B—C8B—H8BA119.5N2B—C17B—H17D110.0
C4A—C9A—C8A121.1 (2)C16B—C17B—H17D110.0
C4A—C9A—N1A119.0 (2)H17C—C17B—H17D108.3
C8A—C9A—N1A119.9 (2)O4—C18—O5124.1 (3)
C8B—C9B—N1B120.2 (2)O4—C18—C19116.8 (3)
C8B—C9B—C4B121.0 (2)O5—C18—C19119.0 (3)
N1B—C9B—C4B118.8 (2)C20—C19—C18124.6 (3)
N1A—C10A—C12A120.5 (3)C20—C19—H19A117.7
N1A—C10A—C11A119.4 (2)C18—C19—H19A117.7
C12A—C10A—C11A60.0 (2)C19—C20—C21124.9 (3)
N1A—C10A—H10A115.3C19—C20—H20A117.5
C12A—C10A—H10A115.3C21—C20—H20A117.5
C11A—C10A—H10A115.3O6—C21—O7123.0 (2)
N1B—C10B—C12B119.7 (3)O6—C21—C20117.3 (2)
N1B—C10B—C11B120.0 (3)O7—C21—C20119.7 (2)
C12B—C10B—C11B61.0 (2)
(3) top
Crystal data top
C17H19FN3O3·C4H3O4F(000) = 936
Mr = 447.42Dx = 1.416 Mg m3
Monoclinic, P21/cCu Kα radiation, λ = 1.54178 Å
a = 13.956 (4) ÅCell parameters from 3531 reflections
b = 10.459 (4) Åθ = 3.3–72.4°
c = 15.184 (5) ŵ = 0.96 mm1
β = 108.765 (6)°T = 293 K
V = 2098.5 (12) Å3Prism, colorless
Z = 40.75 × 0.65 × 0.30 mm
Data collection top
CCD
diffractometer
4083 independent reflections
Radiation source: fine-focus sealed tube3531 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.047
Detector resolution: 0 pixels mm-1θmax = 72.4°, θmin = 3.3°
ωκ scansh = 1617
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
k = 1212
Tmin = 0.707, Tmax = 1.000l = 1813
20341 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.042H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.123 w = 1/[σ2(Fo2) + (0.0771P)2 + 0.1645P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4083 reflectionsΔρmax = 0.22 e Å3
311 parametersΔρmin = 0.19 e Å3
2 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (6)
Crystal data top
C17H19FN3O3·C4H3O4V = 2098.5 (12) Å3
Mr = 447.42Z = 4
Monoclinic, P21/cCu Kα radiation
a = 13.956 (4) ŵ = 0.96 mm1
b = 10.459 (4) ÅT = 293 K
c = 15.184 (5) Å0.75 × 0.65 × 0.30 mm
β = 108.765 (6)°
Data collection top
CCD
diffractometer
4083 independent reflections
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
3531 reflections with I > 2σ(I)
Tmin = 0.707, Tmax = 1.000Rint = 0.047
20341 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0422 restraints
wR(F2) = 0.123H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.22 e Å3
4083 reflectionsΔρmin = 0.19 e Å3
311 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.42541 (10)0.70397 (15)0.14347 (9)0.0428 (3)
H1A0.40190.78380.15410.051*
C20.35945 (10)0.60340 (15)0.12676 (9)0.0420 (3)
C30.39203 (9)0.47823 (14)0.11114 (9)0.0397 (3)
C40.49749 (9)0.46793 (13)0.11670 (8)0.0368 (3)
C50.53786 (10)0.34854 (13)0.10474 (9)0.0412 (3)
H5A0.49710.27600.09400.049*
C60.63622 (10)0.33885 (13)0.10881 (10)0.0414 (3)
C70.70340 (9)0.44440 (13)0.12821 (8)0.0360 (3)
C80.66362 (9)0.56165 (13)0.14088 (8)0.0370 (3)
H8A0.70550.63310.15440.044*
C90.56142 (9)0.57471 (13)0.13375 (8)0.0355 (3)
C100.58809 (11)0.80637 (14)0.17056 (10)0.0462 (3)
H10A0.63130.81050.23570.055*
C110.63167 (15)0.86295 (18)0.10240 (14)0.0656 (5)
H11A0.61460.82350.04150.079*
H11B0.69960.89790.12580.079*
C120.54931 (15)0.93130 (18)0.12684 (15)0.0697 (5)
H12A0.56751.00740.16510.084*
H12B0.48250.93310.08070.084*
C130.25457 (11)0.62908 (17)0.12741 (11)0.0514 (4)
C140.86372 (10)0.33388 (14)0.19697 (10)0.0435 (3)
H14A0.82370.25760.19530.052*
H14B0.88270.36900.25940.052*
C150.95734 (10)0.29985 (14)0.17335 (11)0.0473 (3)
H15A0.99750.23920.21860.057*
H15B0.93820.25960.11260.057*
C160.95727 (10)0.51492 (14)0.10897 (9)0.0424 (3)
H16A0.93930.48450.04540.051*
H16B0.99710.59220.11400.051*
C170.86194 (10)0.54488 (13)0.13200 (10)0.0406 (3)
H17A0.87970.58350.19330.049*
H17B0.82120.60560.08720.049*
C180.84463 (11)0.69072 (15)0.39068 (10)0.0467 (3)
C190.81616 (15)0.56073 (18)0.41281 (11)0.0630 (5)
H19A0.77980.51280.36130.076*
C200.83402 (16)0.50133 (17)0.49404 (12)0.0677 (5)
H20A0.80890.41840.49010.081*
C210.88788 (12)0.54675 (15)0.59015 (11)0.0511 (4)
N10.52244 (8)0.69460 (11)0.14555 (8)0.0395 (3)
N20.80343 (8)0.42816 (11)0.13010 (7)0.0378 (3)
N31.01862 (8)0.41604 (12)0.17304 (9)0.0416 (3)
H3A1.0735 (18)0.391 (2)0.1561 (14)0.072 (6)*
H3B1.0470 (15)0.4516 (19)0.2321 (14)0.060 (5)*
O10.22431 (10)0.73433 (14)0.13770 (11)0.0751 (4)
O20.19571 (8)0.52629 (14)0.11620 (9)0.0621 (3)
H2A0.235 (2)0.452 (3)0.113 (2)0.116 (10)*
O30.33433 (7)0.38227 (11)0.09509 (8)0.0523 (3)
O40.89960 (10)0.76240 (12)0.45640 (8)0.0590 (3)
H4A0.910 (3)0.726 (4)0.5073 (15)0.071 (16)*0.57 (7)
O50.81670 (8)0.72729 (13)0.30984 (7)0.0588 (3)
O60.92891 (11)0.65675 (12)0.60334 (8)0.0669 (4)
H6A0.920 (3)0.690 (4)0.5516 (16)0.054 (18)*0.43 (7)
O70.88970 (12)0.47528 (12)0.65499 (8)0.0713 (4)
F10.67006 (7)0.22377 (9)0.09064 (8)0.0606 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0308 (7)0.0496 (8)0.0482 (7)0.0071 (6)0.0129 (5)0.0012 (6)
C20.0267 (6)0.0543 (8)0.0455 (7)0.0046 (6)0.0124 (5)0.0054 (6)
C30.0259 (6)0.0509 (8)0.0412 (6)0.0004 (5)0.0092 (5)0.0054 (5)
C40.0234 (6)0.0453 (7)0.0397 (6)0.0014 (5)0.0074 (4)0.0013 (5)
C50.0278 (6)0.0410 (7)0.0524 (7)0.0051 (5)0.0095 (5)0.0026 (6)
C60.0297 (7)0.0384 (7)0.0546 (7)0.0006 (5)0.0115 (5)0.0038 (6)
C70.0226 (6)0.0429 (7)0.0409 (6)0.0003 (5)0.0078 (4)0.0002 (5)
C80.0235 (6)0.0412 (7)0.0443 (6)0.0034 (5)0.0082 (5)0.0033 (5)
C90.0249 (6)0.0415 (7)0.0377 (6)0.0009 (5)0.0069 (4)0.0016 (5)
C100.0361 (7)0.0419 (7)0.0553 (7)0.0019 (6)0.0074 (6)0.0076 (6)
C110.0570 (10)0.0607 (10)0.0797 (11)0.0195 (8)0.0228 (8)0.0056 (9)
C120.0556 (10)0.0460 (9)0.0973 (13)0.0008 (8)0.0103 (9)0.0051 (9)
C130.0312 (7)0.0664 (10)0.0590 (8)0.0087 (7)0.0177 (6)0.0086 (7)
C140.0293 (6)0.0453 (7)0.0557 (7)0.0025 (5)0.0132 (5)0.0094 (6)
C150.0295 (7)0.0404 (7)0.0710 (9)0.0034 (5)0.0147 (6)0.0052 (6)
C160.0271 (6)0.0496 (8)0.0509 (7)0.0007 (6)0.0133 (5)0.0077 (6)
C170.0252 (6)0.0397 (7)0.0569 (7)0.0011 (5)0.0133 (5)0.0040 (6)
C180.0372 (7)0.0554 (8)0.0480 (7)0.0050 (6)0.0144 (6)0.0055 (6)
C190.0721 (11)0.0582 (10)0.0508 (8)0.0218 (8)0.0088 (7)0.0129 (7)
C200.0863 (13)0.0457 (9)0.0624 (10)0.0184 (9)0.0119 (9)0.0056 (7)
C210.0527 (9)0.0420 (8)0.0539 (8)0.0040 (6)0.0105 (6)0.0001 (6)
N10.0271 (5)0.0419 (6)0.0476 (6)0.0012 (4)0.0093 (4)0.0028 (5)
N20.0225 (5)0.0398 (6)0.0506 (6)0.0012 (4)0.0113 (4)0.0027 (5)
N30.0242 (5)0.0447 (6)0.0552 (7)0.0028 (5)0.0119 (5)0.0014 (5)
O10.0483 (7)0.0740 (9)0.1130 (10)0.0182 (6)0.0401 (7)0.0054 (8)
O20.0294 (5)0.0746 (8)0.0861 (8)0.0006 (5)0.0241 (5)0.0051 (6)
O30.0279 (5)0.0550 (6)0.0736 (7)0.0073 (4)0.0160 (4)0.0026 (5)
O40.0694 (8)0.0556 (7)0.0492 (6)0.0213 (6)0.0149 (5)0.0050 (5)
O50.0467 (6)0.0764 (8)0.0504 (6)0.0080 (5)0.0116 (5)0.0025 (5)
O60.0860 (9)0.0551 (7)0.0489 (6)0.0196 (6)0.0069 (6)0.0028 (5)
O70.0921 (10)0.0515 (7)0.0596 (7)0.0039 (6)0.0095 (6)0.0101 (5)
F10.0386 (5)0.0415 (5)0.1010 (7)0.0000 (4)0.0214 (4)0.0153 (4)
Geometric parameters (Å, º) top
C1—N11.3479 (18)C14—N21.4702 (17)
C1—C21.367 (2)C14—C151.505 (2)
C1—H1A0.9300C14—H14A0.9700
C2—C31.430 (2)C14—H14B0.9700
C2—C131.4913 (19)C15—N31.4869 (19)
C3—O31.2605 (18)C15—H15A0.9700
C3—C41.4508 (18)C15—H15B0.9700
C4—C91.4006 (19)C16—N31.4876 (18)
C4—C51.406 (2)C16—C171.5132 (18)
C5—C61.358 (2)C16—H16A0.9700
C5—H5A0.9300C16—H16B0.9700
C6—F11.3534 (16)C17—N21.4638 (18)
C6—C71.4166 (19)C17—H17A0.9700
C7—C81.3849 (19)C17—H17B0.9700
C7—N21.3974 (16)C18—O51.2235 (19)
C8—C91.4018 (18)C18—O41.2860 (18)
C8—H8A0.9300C18—C191.485 (2)
C9—N11.4012 (18)C19—C201.331 (3)
C10—N11.4582 (19)C19—H19A0.9300
C10—C111.482 (3)C20—C211.488 (2)
C10—C121.487 (2)C20—H20A0.9300
C10—H10A0.9800C21—O71.230 (2)
C11—C121.498 (3)C21—O61.272 (2)
C11—H11A0.9700N3—H3A0.92 (2)
C11—H11B0.9700N3—H3B0.93 (2)
C12—H12A0.9700O2—H2A0.96 (3)
C12—H12B0.9700O4—H4A0.830 (10)
C13—O11.207 (2)O6—H6A0.829 (10)
C13—O21.330 (2)
N1—C1—C2124.05 (13)C15—C14—H14A109.7
N1—C1—H1A118.0N2—C14—H14B109.7
C2—C1—H1A118.0C15—C14—H14B109.7
C1—C2—C3120.28 (12)H14A—C14—H14B108.2
C1—C2—C13117.64 (14)N3—C15—C14110.60 (12)
C3—C2—C13122.07 (13)N3—C15—H15A109.5
O3—C3—C2122.91 (12)C14—C15—H15A109.5
O3—C3—C4121.68 (13)N3—C15—H15B109.5
C2—C3—C4115.39 (12)C14—C15—H15B109.5
C9—C4—C5118.31 (12)H15A—C15—H15B108.1
C9—C4—C3121.71 (12)N3—C16—C17110.89 (11)
C5—C4—C3119.98 (12)N3—C16—H16A109.5
C6—C5—C4120.12 (12)C17—C16—H16A109.5
C6—C5—H5A119.9N3—C16—H16B109.5
C4—C5—H5A119.9C17—C16—H16B109.5
F1—C6—C5118.10 (12)H16A—C16—H16B108.0
F1—C6—C7118.98 (12)N2—C17—C16110.43 (11)
C5—C6—C7122.89 (12)N2—C17—H17A109.6
C8—C7—N2123.18 (11)C16—C17—H17A109.6
C8—C7—C6116.79 (11)N2—C17—H17B109.6
N2—C7—C6119.97 (12)C16—C17—H17B109.6
C7—C8—C9121.27 (12)H17A—C17—H17B108.1
C7—C8—H8A119.4O5—C18—O4120.95 (15)
C9—C8—H8A119.4O5—C18—C19119.42 (13)
C4—C9—N1119.13 (11)O4—C18—C19119.63 (13)
C4—C9—C8120.56 (12)C20—C19—C18130.78 (14)
N1—C9—C8120.30 (11)C20—C19—H19A114.6
N1—C10—C11120.19 (13)C18—C19—H19A114.6
N1—C10—C12118.71 (13)C19—C20—C21130.14 (16)
C11—C10—C1260.61 (13)C19—C20—H20A114.9
N1—C10—H10A115.4C21—C20—H20A114.9
C11—C10—H10A115.4O7—C21—O6122.10 (15)
C12—C10—H10A115.4O7—C21—C20117.70 (15)
C10—C11—C1259.84 (12)O6—C21—C20120.19 (14)
C10—C11—H11A117.8C1—N1—C9119.38 (12)
C12—C11—H11A117.8C1—N1—C10119.35 (12)
C10—C11—H11B117.8C9—N1—C10120.90 (11)
C12—C11—H11B117.8C7—N2—C17116.51 (11)
H11A—C11—H11B114.9C7—N2—C14116.21 (10)
C10—C12—C1159.54 (12)C17—N2—C14110.73 (10)
C10—C12—H12A117.8C15—N3—C16111.08 (11)
C11—C12—H12A117.8C15—N3—H3A107.7 (14)
C10—C12—H12B117.8C16—N3—H3A111.5 (13)
C11—C12—H12B117.8C15—N3—H3B112.9 (12)
H12A—C12—H12B115.0C16—N3—H3B109.2 (12)
O1—C13—O2121.74 (14)H3A—N3—H3B104.2 (18)
O1—C13—C2123.38 (16)C13—O2—H2A109.0 (19)
O2—C13—C2114.87 (14)C18—O4—H4A110 (3)
N2—C14—C15110.00 (11)C21—O6—H6A108 (3)
N2—C14—H14A109.7
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O5i0.92 (2)2.25 (2)2.9770 (18)135.7 (18)
N3—H3A···O4i0.92 (2)2.30 (2)3.0317 (18)136.1 (18)
N3—H3A···O2ii0.92 (2)2.43 (2)3.0911 (17)128.4 (18)
N3—H3B···O7iii0.93 (2)1.82 (2)2.7564 (19)175.8 (18)
O2—H2A···O30.96 (3)1.67 (3)2.5521 (17)151 (3)
O4—H4A···O60.83 (1)1.57 (1)2.4039 (17)179 (5)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+2, y+1, z+1.
(4) top
Crystal data top
C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O)Z = 2
Mr = 980.96F(000) = 1036
Triclinic, P1Dx = 1.403 Mg m3
a = 10.225 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 13.8350 (6) ÅCell parameters from 7818 reflections
c = 18.560 (7) Åθ = 4.7–66.0°
α = 72.83 (4)°µ = 0.96 mm1
β = 86.82 (6)°T = 293 K
γ = 68.03 (5)°Prism, colorless
V = 2321.9 (10) Å30.64 × 0.43 × 0.07 mm
Data collection top
CCD
diffractometer
7818 independent reflections
Radiation source: fine-focus sealed tube4946 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.073
Detector resolution: 0 pixels mm-1θmax = 66.0°, θmin = 4.7°
ωκ scansh = 115
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
k = 1616
Tmin = 0.456, Tmax = 1.000l = 2121
23976 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.074H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.218 w = 1/[σ2(Fo2) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.13(Δ/σ)max = 0.004
7818 reflectionsΔρmax = 0.71 e Å3
677 parametersΔρmin = 0.34 e Å3
15 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0009 (2)
Crystal data top
C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O)γ = 68.03 (5)°
Mr = 980.96V = 2321.9 (10) Å3
Triclinic, P1Z = 2
a = 10.225 (2) ÅCu Kα radiation
b = 13.8350 (6) ŵ = 0.96 mm1
c = 18.560 (7) ÅT = 293 K
α = 72.83 (4)°0.64 × 0.43 × 0.07 mm
β = 86.82 (6)°
Data collection top
CCD
diffractometer
7818 independent reflections
Absorption correction: multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
4946 reflections with I > 2σ(I)
Tmin = 0.456, Tmax = 1.000Rint = 0.073
23976 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07415 restraints
wR(F2) = 0.218H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.71 e Å3
7818 reflectionsΔρmin = 0.34 e Å3
677 parameters
Special details top

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
F1A0.2935 (2)0.29579 (19)0.44355 (13)0.0826 (7)
F1B1.2509 (2)0.16831 (16)0.58960 (10)0.0648 (5)
N1A0.7307 (2)0.44472 (17)0.39827 (14)0.0437 (6)
N1B0.7885 (2)0.06533 (17)0.56138 (13)0.0430 (6)
N2A0.3597 (3)0.3709 (2)0.29820 (16)0.0579 (7)
N2B1.1405 (3)0.07845 (19)0.72053 (13)0.0476 (6)
N3A0.2316 (3)0.3096 (2)0.19826 (17)0.0596 (8)
H3AA0.200 (4)0.259 (3)0.197 (3)0.091 (13)*
H3AB0.188 (4)0.372 (2)0.164 (2)0.090 (14)*
N3B1.2875 (3)0.0213 (2)0.86166 (16)0.0544 (7)
H3BA1.370 (3)0.015 (3)0.887 (2)0.073 (11)*
H3BB1.228 (4)0.068 (3)0.882 (2)0.087 (14)*
O1A0.9673 (3)0.4222 (3)0.58144 (17)0.0962 (10)
O1B0.6170 (2)0.11912 (18)0.34922 (13)0.0654 (7)
O2A0.8328 (3)0.3579 (2)0.66253 (15)0.0762 (8)
H2AA0.761 (4)0.345 (4)0.658 (3)0.12 (2)*
O2B0.7685 (3)0.19279 (18)0.29148 (13)0.0590 (6)
H2BA0.826 (4)0.211 (3)0.308 (2)0.089 (14)*
O3A0.6245 (2)0.33028 (18)0.61512 (13)0.0602 (6)
O3B0.9494 (2)0.21080 (16)0.37021 (12)0.0532 (5)
O41.4400 (3)0.12180 (19)1.08156 (15)0.0734 (8)
O51.3799 (2)0.07063 (18)0.99019 (14)0.0659 (7)
H5A1.50000.00001.00000.14 (3)*
O61.0423 (3)0.44141 (19)0.87245 (16)0.0786 (8)
O70.8456 (3)0.51603 (19)0.92689 (16)0.0796 (8)
O81.1327 (2)0.22795 (17)0.89539 (11)0.0523 (5)
H8A1.116 (4)0.2937 (17)0.875 (2)0.090 (14)*
O91.0600 (3)0.09705 (17)1.07993 (13)0.0628 (6)
O101.0511 (2)0.07025 (16)0.96819 (12)0.0569 (6)
H10E1.00000.00001.00000.092 (18)*
O110.6303 (7)0.3351 (5)0.8892 (3)0.185 (2)
O121.0786 (4)0.1784 (3)1.19615 (16)0.0768 (8)
H12E1.008 (3)0.235 (2)1.184 (3)0.086 (17)*
H12F1.064 (4)0.154 (3)1.1612 (17)0.070 (11)*
O131.1398 (4)0.6144 (3)0.8325 (2)0.0975 (10)
H13A1.121 (5)0.558 (3)0.849 (3)0.117*
H13B1.204 (4)0.594 (4)0.855 (3)0.117*
O14A1.3839 (12)0.5178 (12)1.0379 (8)0.079 (6)0.187 (8)
H14E1.37970.56241.06200.094*0.187 (8)
H14F1.30720.50251.05320.094*0.187 (8)
O14B1.3545 (8)0.5264 (7)0.9477 (6)0.289 (7)0.813 (8)
H14G1.43880.51310.95500.347*0.813 (8)
H14H1.28630.54570.96750.347*0.813 (8)
C1A0.8051 (3)0.4380 (2)0.45839 (18)0.0475 (7)
H1AA0.88050.46120.44980.057*
C1B0.7356 (3)0.0837 (2)0.49177 (17)0.0435 (7)
H1BA0.66100.06220.48770.052*
C2A0.7753 (3)0.3988 (2)0.53164 (18)0.0472 (7)
C2B0.7850 (3)0.1322 (2)0.42611 (16)0.0406 (6)
C3A0.6591 (3)0.3645 (2)0.54775 (18)0.0457 (7)
C3B0.8996 (3)0.1655 (2)0.42926 (16)0.0405 (6)
C4A0.5809 (3)0.3699 (2)0.48286 (17)0.0428 (7)
C4B0.9585 (3)0.14477 (19)0.50387 (15)0.0379 (6)
C5A0.4664 (3)0.3346 (2)0.49266 (18)0.0502 (7)
H5AA0.43880.30980.54100.060*
C5B1.0750 (3)0.1709 (2)0.51371 (16)0.0427 (7)
H5BA1.11380.20370.47160.051*
C6A0.3968 (3)0.3368 (2)0.43196 (19)0.0533 (8)
C6B1.1318 (3)0.1493 (2)0.58355 (17)0.0444 (7)
C7A0.4315 (3)0.3755 (2)0.35738 (18)0.0470 (7)
C7B1.0756 (3)0.1021 (2)0.65111 (16)0.0410 (6)
C8A0.5444 (3)0.4100 (2)0.34766 (18)0.0460 (7)
H8AA0.57120.43460.29910.055*
C8B0.9611 (3)0.0754 (2)0.64118 (16)0.0415 (6)
H8BA0.92150.04360.68340.050*
C9A0.6183 (3)0.4085 (2)0.40906 (17)0.0422 (6)
C9B0.9036 (3)0.0952 (2)0.56908 (16)0.0392 (6)
C10A0.7700 (3)0.4849 (2)0.32148 (18)0.0517 (7)
H10A0.81310.42990.29500.062*
C10B0.7378 (3)0.0050 (2)0.62822 (18)0.0506 (7)
H10B0.80200.07030.65190.061*
C11A0.6768 (4)0.5942 (3)0.2739 (2)0.0647 (9)
H11A0.59550.63560.29650.078*
H11B0.66270.60420.22060.078*
C11B0.6520 (4)0.0627 (3)0.6810 (2)0.0671 (9)
H11C0.62960.14050.66880.081*
H11D0.66600.02370.73450.081*
C12A0.8205 (4)0.5765 (3)0.3027 (2)0.0665 (9)
H12A0.89310.57580.26670.080*
H12B0.82600.60720.34260.080*
C12B0.5861 (4)0.0239 (3)0.6308 (2)0.0693 (10)
H12C0.56010.03840.65400.083*
H12D0.52370.07840.58840.083*
C13A0.8675 (4)0.3949 (3)0.5924 (2)0.0619 (9)
C13B0.7158 (3)0.1463 (2)0.35353 (18)0.0492 (7)
C14A0.2069 (3)0.4091 (3)0.2907 (2)0.0587 (8)
H14A0.16970.47940.25240.070*
H14B0.16770.41790.33830.070*
C14B1.1845 (4)0.1575 (2)0.74016 (18)0.0544 (8)
H14C1.10940.20150.76460.065*
H14D1.20350.20570.69470.065*
C15A0.1650 (4)0.3275 (3)0.2689 (2)0.0613 (9)
H15A0.19540.25900.30910.074*
H15B0.06310.35440.26120.074*
C15B1.3150 (4)0.0976 (3)0.79233 (19)0.0590 (8)
H15C1.39140.05680.76680.071*
H15D1.34340.14950.80630.071*
C16A0.3863 (4)0.2795 (3)0.2024 (2)0.0608 (9)
H16A0.42220.27630.15330.073*
H16B0.43060.20780.23840.073*
C16B1.2319 (3)0.0543 (2)0.84268 (18)0.0542 (8)
H16C1.20610.09740.88850.065*
H16D1.30520.10390.82090.065*
C17A0.4233 (4)0.3624 (3)0.2266 (2)0.0611 (9)
H17A0.52500.33930.23280.073*
H17B0.38730.43280.18830.073*
C17B1.1042 (3)0.0085 (2)0.78732 (17)0.0499 (7)
H17C1.07350.04200.77300.060*
H17D1.02720.05250.81080.060*
C181.3567 (3)0.1346 (2)1.03121 (18)0.0495 (7)
C191.2186 (3)0.2321 (2)1.01449 (17)0.0470 (7)
H19A1.23800.29550.98520.056*
H19B1.18490.24441.06210.056*
C201.0987 (3)0.2264 (2)0.97223 (15)0.0432 (7)
C210.9608 (3)0.3238 (2)0.97133 (18)0.0514 (7)
H21A0.88300.30810.95660.062*
H21B0.94750.32841.02250.062*
C220.9502 (4)0.4345 (3)0.9204 (2)0.0630 (10)
C231.0703 (3)0.1230 (2)1.01075 (17)0.0442 (7)
C240.6974 (8)0.3194 (5)0.8251 (3)0.122 (2)
H24A0.78840.32600.82570.147*
H24B0.64100.37360.78060.147*
C250.7154 (9)0.2124 (5)0.8240 (5)0.156 (3)
H25A0.68240.21500.77520.188*
H25B0.81440.16500.83320.188*
C260.6349 (12)0.1726 (6)0.8820 (7)0.205 (5)
H26A0.54450.18170.86130.246*
H26B0.68550.09590.90810.246*
C270.6166 (14)0.2366 (11)0.9308 (5)0.233 (6)
H27A0.68740.19840.97270.279*
H27B0.52400.25120.95100.279*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F1A0.0958 (16)0.1116 (16)0.0677 (14)0.0759 (13)0.0034 (11)0.0159 (12)
F1B0.0691 (12)0.0948 (13)0.0470 (11)0.0530 (10)0.0092 (9)0.0134 (10)
N1A0.0546 (14)0.0462 (13)0.0385 (14)0.0245 (10)0.0037 (10)0.0161 (11)
N1B0.0513 (13)0.0473 (12)0.0378 (13)0.0263 (10)0.0065 (10)0.0111 (10)
N2A0.0552 (15)0.0769 (17)0.0558 (17)0.0269 (13)0.0070 (12)0.0353 (14)
N2B0.0681 (16)0.0565 (14)0.0308 (13)0.0357 (12)0.0081 (11)0.0129 (11)
N3A0.087 (2)0.0504 (16)0.0509 (17)0.0341 (15)0.0169 (15)0.0146 (14)
N3B0.0567 (17)0.0678 (17)0.0440 (16)0.0202 (14)0.0109 (13)0.0258 (14)
O1A0.111 (2)0.143 (3)0.0682 (19)0.087 (2)0.0164 (16)0.0246 (18)
O1B0.0748 (15)0.0750 (15)0.0561 (15)0.0384 (12)0.0208 (12)0.0154 (12)
O2A0.098 (2)0.0944 (18)0.0490 (16)0.0462 (16)0.0129 (14)0.0229 (14)
O2B0.0734 (15)0.0702 (14)0.0376 (13)0.0308 (12)0.0116 (11)0.0142 (11)
O3A0.0777 (15)0.0682 (14)0.0392 (13)0.0314 (11)0.0006 (11)0.0165 (11)
O3B0.0673 (14)0.0622 (12)0.0345 (12)0.0320 (10)0.0037 (10)0.0090 (10)
O40.0756 (16)0.0805 (15)0.0660 (17)0.0177 (12)0.0291 (13)0.0337 (13)
O50.0642 (14)0.0673 (14)0.0683 (16)0.0090 (11)0.0211 (12)0.0389 (12)
O60.113 (2)0.0563 (14)0.0578 (17)0.0308 (14)0.0063 (15)0.0058 (12)
O70.0927 (19)0.0532 (14)0.0717 (19)0.0055 (13)0.0160 (14)0.0130 (13)
O80.0798 (15)0.0509 (13)0.0305 (12)0.0274 (10)0.0008 (10)0.0138 (10)
O90.1074 (19)0.0606 (13)0.0391 (13)0.0503 (12)0.0051 (12)0.0171 (10)
O100.0869 (16)0.0574 (12)0.0463 (13)0.0414 (11)0.0004 (11)0.0242 (10)
O110.288 (7)0.205 (5)0.135 (5)0.151 (5)0.089 (5)0.092 (4)
O120.116 (3)0.093 (2)0.0544 (17)0.066 (2)0.0045 (16)0.0337 (16)
O130.131 (3)0.099 (2)0.079 (2)0.059 (2)0.0012 (19)0.0267 (19)
O14A0.038 (7)0.126 (12)0.054 (9)0.004 (6)0.007 (5)0.036 (8)
O14B0.143 (6)0.308 (10)0.402 (16)0.008 (6)0.129 (8)0.159 (10)
C1A0.0560 (17)0.0476 (15)0.0474 (18)0.0250 (13)0.0077 (14)0.0173 (13)
C1B0.0468 (15)0.0438 (14)0.0462 (17)0.0195 (11)0.0089 (13)0.0168 (13)
C2A0.0625 (18)0.0442 (15)0.0416 (17)0.0219 (13)0.0101 (13)0.0173 (13)
C2B0.0489 (15)0.0397 (14)0.0354 (16)0.0161 (11)0.0069 (12)0.0133 (12)
C3A0.0574 (17)0.0396 (14)0.0410 (17)0.0147 (12)0.0044 (13)0.0165 (13)
C3B0.0517 (16)0.0371 (14)0.0333 (15)0.0156 (11)0.0054 (12)0.0114 (12)
C4A0.0542 (16)0.0411 (14)0.0382 (16)0.0189 (12)0.0040 (12)0.0164 (12)
C4B0.0463 (15)0.0375 (13)0.0352 (15)0.0172 (11)0.0022 (11)0.0154 (11)
C5A0.0602 (18)0.0524 (17)0.0461 (18)0.0286 (14)0.0010 (14)0.0162 (14)
C5B0.0535 (16)0.0486 (15)0.0315 (15)0.0250 (12)0.0054 (12)0.0104 (12)
C6A0.0592 (18)0.0581 (17)0.055 (2)0.0343 (14)0.0034 (15)0.0177 (15)
C6B0.0489 (16)0.0531 (16)0.0410 (16)0.0274 (12)0.0002 (12)0.0167 (13)
C7A0.0572 (17)0.0465 (15)0.0446 (18)0.0218 (13)0.0057 (13)0.0192 (13)
C7B0.0534 (16)0.0444 (14)0.0304 (15)0.0218 (12)0.0039 (12)0.0126 (12)
C8A0.0576 (17)0.0475 (15)0.0417 (17)0.0231 (13)0.0065 (13)0.0196 (13)
C8B0.0495 (16)0.0474 (15)0.0340 (15)0.0227 (12)0.0026 (12)0.0142 (12)
C9A0.0523 (16)0.0380 (14)0.0415 (17)0.0186 (12)0.0029 (12)0.0160 (12)
C9B0.0439 (15)0.0381 (13)0.0388 (16)0.0164 (11)0.0047 (11)0.0133 (12)
C10A0.0612 (19)0.0587 (18)0.0430 (18)0.0306 (14)0.0017 (14)0.0155 (14)
C10B0.0588 (18)0.0545 (17)0.0438 (18)0.0301 (14)0.0013 (14)0.0101 (14)
C11A0.073 (2)0.068 (2)0.049 (2)0.0302 (17)0.0076 (16)0.0047 (16)
C11B0.074 (2)0.080 (2)0.057 (2)0.0388 (18)0.0107 (17)0.0228 (18)
C12A0.082 (2)0.070 (2)0.054 (2)0.0438 (18)0.0076 (17)0.0050 (17)
C12B0.064 (2)0.085 (2)0.063 (2)0.0430 (18)0.0041 (17)0.0081 (19)
C13A0.083 (2)0.065 (2)0.047 (2)0.0348 (18)0.0123 (17)0.0189 (17)
C13B0.0604 (18)0.0457 (15)0.0439 (18)0.0185 (13)0.0139 (14)0.0153 (14)
C14A0.0601 (19)0.0661 (19)0.061 (2)0.0271 (15)0.0085 (16)0.0276 (17)
C14B0.077 (2)0.0557 (17)0.0424 (18)0.0347 (15)0.0070 (15)0.0177 (14)
C15A0.075 (2)0.069 (2)0.053 (2)0.0391 (17)0.0058 (17)0.0210 (17)
C15B0.070 (2)0.077 (2)0.049 (2)0.0416 (17)0.0029 (15)0.0260 (17)
C16A0.071 (2)0.0612 (19)0.048 (2)0.0163 (15)0.0152 (16)0.0207 (16)
C16B0.066 (2)0.0612 (18)0.0389 (17)0.0267 (15)0.0070 (14)0.0148 (14)
C17A0.067 (2)0.073 (2)0.050 (2)0.0270 (16)0.0057 (16)0.0250 (17)
C17B0.0626 (18)0.0608 (17)0.0340 (16)0.0320 (14)0.0069 (13)0.0116 (14)
C180.0574 (18)0.0509 (16)0.0476 (18)0.0265 (13)0.0061 (14)0.0157 (14)
C190.0615 (18)0.0478 (15)0.0411 (17)0.0269 (13)0.0076 (13)0.0164 (13)
C200.0619 (17)0.0448 (15)0.0290 (15)0.0232 (12)0.0038 (12)0.0144 (12)
C210.0610 (19)0.0489 (16)0.0450 (18)0.0198 (13)0.0045 (14)0.0145 (14)
C220.084 (3)0.0527 (19)0.049 (2)0.0205 (18)0.0233 (18)0.0117 (16)
C230.0559 (17)0.0462 (15)0.0378 (17)0.0232 (12)0.0051 (12)0.0163 (13)
C240.178 (6)0.145 (5)0.077 (4)0.101 (5)0.009 (4)0.028 (3)
C250.192 (8)0.100 (5)0.147 (7)0.035 (4)0.021 (6)0.023 (4)
C260.258 (11)0.110 (5)0.227 (12)0.095 (6)0.018 (9)0.017 (6)
C270.349 (15)0.336 (15)0.101 (6)0.261 (14)0.075 (8)0.029 (8)
Geometric parameters (Å, º) top
F1A—C6A1.355 (4)C5B—C6B1.353 (4)
F1B—C6B1.355 (3)C5B—H5BA0.9300
N1A—C1A1.346 (3)C6A—C7A1.407 (5)
N1A—C9A1.399 (4)C6B—C7B1.431 (4)
N1A—C10A1.462 (4)C7A—C8A1.390 (4)
N1B—C1B1.345 (4)C7B—C8B1.389 (4)
N1B—C9B1.412 (3)C8A—C9A1.393 (4)
N1B—C10B1.465 (4)C8A—H8AA0.9300
N2A—C7A1.384 (4)C8B—C9B1.400 (4)
N2A—C14A1.450 (4)C8B—H8BA0.9300
N2A—C17A1.464 (5)C10A—C11A1.484 (5)
N2B—C7B1.375 (3)C10A—C12A1.484 (4)
N2B—C17B1.456 (4)C10A—H10A0.9800
N2B—C14B1.467 (3)C10B—C12B1.474 (5)
N3A—C16A1.478 (5)C10B—C11B1.486 (5)
N3A—C15A1.485 (5)C10B—H10B0.9800
N3A—H3AA0.878 (19)C11A—C12A1.498 (5)
N3A—H3AB0.879 (19)C11A—H11A0.9700
N3B—C16B1.492 (4)C11A—H11B0.9700
N3B—C15B1.493 (5)C11B—C12B1.498 (5)
N3B—H3BA0.879 (19)C11B—H11C0.9700
N3B—H3BB0.870 (19)C11B—H11D0.9700
O1A—C13A1.202 (5)C12A—H12A0.9700
O1B—C13B1.216 (4)C12A—H12B0.9700
O2A—C13A1.331 (5)C12B—H12C0.9700
O2A—H2AA0.84 (2)C12B—H12D0.9700
O2B—C13B1.335 (4)C14A—C15A1.508 (4)
O2B—H2BA0.825 (19)C14A—H14A0.9700
O3A—C3A1.281 (4)C14A—H14B0.9700
O3B—C3B1.274 (4)C14B—C15B1.499 (4)
O4—C181.228 (3)C14B—H14C0.9700
O5—C181.281 (4)C14B—H14D0.9700
O5—H5A1.232 (2)C15A—H15A0.9700
O6—C221.269 (5)C15A—H15B0.9700
O7—C221.263 (4)C15B—H15C0.9700
O8—C201.445 (3)C15B—H15D0.9700
O8—H8A0.829 (19)C16A—C17A1.519 (4)
O9—C231.237 (4)C16A—H16A0.9700
O10—C231.288 (3)C16A—H16B0.9700
O10—H10E1.254 (2)C16B—C17B1.513 (4)
O11—C241.372 (7)C16B—H16C0.9700
O11—C271.408 (10)C16B—H16D0.9700
O12—H12E0.825 (19)C17A—H17A0.9700
O12—H12F0.853 (19)C17A—H17B0.9700
O13—H13A0.839 (19)C17B—H17C0.9700
O13—H13B0.72 (2)C17B—H17D0.9700
O14A—H14E0.8509C18—C191.511 (4)
O14A—H14F0.8973C19—C201.530 (4)
O14B—H14G0.8207C19—H19A0.9700
O14B—H14H0.7645C19—H19B0.9700
C1A—C2A1.370 (5)C20—C231.525 (4)
C1A—H1AA0.9300C20—C211.540 (4)
C1B—C2B1.376 (4)C21—C221.511 (5)
C1B—H1BA0.9300C21—H21A0.9700
C2A—C3A1.423 (4)C21—H21B0.9700
C2A—C13A1.486 (4)C24—C251.428 (8)
C2B—C3B1.421 (4)C24—H24A0.9700
C2B—C13B1.483 (4)C24—H24B0.9700
C3A—C4A1.451 (4)C25—C261.425 (12)
C3B—C4B1.446 (4)C25—H25A0.9700
C4A—C9A1.404 (4)C25—H25B0.9700
C4A—C5A1.411 (4)C26—C271.404 (12)
C4B—C5B1.404 (4)C26—H26A0.9700
C4B—C9B1.404 (4)C26—H26B0.9700
C5A—C6A1.353 (4)C27—H27A0.9700
C5A—H5AA0.9300C27—H27B0.9700
C1A—N1A—C9A120.0 (3)C10A—C12A—H12B117.8
C1A—N1A—C10A120.7 (2)C11A—C12A—H12B117.8
C9A—N1A—C10A119.3 (2)H12A—C12A—H12B114.9
C1B—N1B—C9B119.1 (3)C10B—C12B—C11B60.0 (2)
C1B—N1B—C10B120.6 (2)C10B—C12B—H12C117.8
C9B—N1B—C10B119.9 (2)C11B—C12B—H12C117.8
C7A—N2A—C14A122.9 (3)C10B—C12B—H12D117.8
C7A—N2A—C17A122.3 (3)C11B—C12B—H12D117.8
C14A—N2A—C17A111.8 (3)H12C—C12B—H12D114.9
C7B—N2B—C17B120.1 (2)O1A—C13A—O2A120.5 (3)
C7B—N2B—C14B121.5 (2)O1A—C13A—C2A124.3 (3)
C17B—N2B—C14B111.1 (2)O2A—C13A—C2A115.2 (3)
C16A—N3A—C15A113.3 (3)O1B—C13B—O2B121.0 (3)
C16A—N3A—H3AA118 (3)O1B—C13B—C2B123.6 (3)
C15A—N3A—H3AA96 (3)O2B—C13B—C2B115.4 (3)
C16A—N3A—H3AB112 (3)N2A—C14A—C15A109.4 (3)
C15A—N3A—H3AB104 (3)N2A—C14A—H14A109.8
H3AA—N3A—H3AB112 (4)C15A—C14A—H14A109.8
C16B—N3B—C15B111.7 (2)N2A—C14A—H14B109.8
C16B—N3B—H3BA111 (2)C15A—C14A—H14B109.8
C15B—N3B—H3BA104 (3)H14A—C14A—H14B108.2
C16B—N3B—H3BB115 (3)N2B—C14B—C15B109.3 (2)
C15B—N3B—H3BB100 (3)N2B—C14B—H14C109.8
H3BA—N3B—H3BB113 (4)C15B—C14B—H14C109.8
C13A—O2A—H2AA105 (4)N2B—C14B—H14D109.8
C13B—O2B—H2BA104 (3)C15B—C14B—H14D109.8
C18—O5—H5A114.2 (2)H14C—C14B—H14D108.3
C20—O8—H8A101 (3)N3A—C15A—C14A109.7 (3)
C23—O10—H10E114.7 (2)N3A—C15A—H15A109.7
C24—O11—C27107.8 (6)C14A—C15A—H15A109.7
H12E—O12—H12F95 (4)N3A—C15A—H15B109.7
H13A—O13—H13B96 (6)C14A—C15A—H15B109.7
H14E—O14A—H14F100.8H15A—C15A—H15B108.2
H14G—O14B—H14H137.5N3B—C15B—C14B110.1 (3)
N1A—C1A—C2A123.4 (3)N3B—C15B—H15C109.6
N1A—C1A—H1AA118.3C14B—C15B—H15C109.6
C2A—C1A—H1AA118.3N3B—C15B—H15D109.6
N1B—C1B—C2B124.1 (2)C14B—C15B—H15D109.6
N1B—C1B—H1BA118.0H15C—C15B—H15D108.2
C2B—C1B—H1BA118.0N3A—C16A—C17A110.5 (3)
C1A—C2A—C3A120.4 (3)N3A—C16A—H16A109.5
C1A—C2A—C13A117.5 (3)C17A—C16A—H16A109.5
C3A—C2A—C13A122.0 (3)N3A—C16A—H16B109.5
C1B—C2B—C3B120.1 (2)C17A—C16A—H16B109.5
C1B—C2B—C13B117.7 (3)H16A—C16A—H16B108.1
C3B—C2B—C13B122.2 (3)N3B—C16B—C17B110.9 (2)
O3A—C3A—C2A122.8 (3)N3B—C16B—H16C109.4
O3A—C3A—C4A121.1 (3)C17B—C16B—H16C109.4
C2A—C3A—C4A116.0 (3)N3B—C16B—H16D109.5
O3B—C3B—C2B122.6 (2)C17B—C16B—H16D109.4
O3B—C3B—C4B121.2 (2)H16C—C16B—H16D108.0
C2B—C3B—C4B116.2 (3)N2A—C17A—C16A108.4 (3)
C9A—C4A—C5A118.4 (3)N2A—C17A—H17A110.0
C9A—C4A—C3A121.0 (3)C16A—C17A—H17A110.0
C5A—C4A—C3A120.6 (3)N2A—C17A—H17B110.0
C5B—C4B—C9B117.5 (2)C16A—C17A—H17B110.0
C5B—C4B—C3B121.1 (3)H17A—C17A—H17B108.4
C9B—C4B—C3B121.3 (2)N2B—C17B—C16B109.5 (3)
C6A—C5A—C4A120.2 (3)N2B—C17B—H17C109.8
C6A—C5A—H5AA119.9C16B—C17B—H17C109.8
C4A—C5A—H5AA119.9N2B—C17B—H17D109.8
C6B—C5B—C4B121.0 (3)C16B—C17B—H17D109.8
C6B—C5B—H5BA119.5H17C—C17B—H17D108.2
C4B—C5B—H5BA119.5O4—C18—O5123.9 (3)
C5A—C6A—F1A118.7 (3)O4—C18—C19119.3 (3)
C5A—C6A—C7A122.6 (3)O5—C18—C19116.8 (2)
F1A—C6A—C7A118.6 (3)C18—C19—C20117.5 (2)
C5B—C6B—F1B118.6 (3)C18—C19—H19A107.9
C5B—C6B—C7B122.8 (3)C20—C19—H19A107.9
F1B—C6B—C7B118.6 (2)C18—C19—H19B107.9
N2A—C7A—C8A123.2 (3)C20—C19—H19B107.9
N2A—C7A—C6A119.5 (3)H19A—C19—H19B107.2
C8A—C7A—C6A117.2 (3)O8—C20—C23108.4 (2)
N2B—C7B—C8B123.5 (3)O8—C20—C19110.7 (3)
N2B—C7B—C6B120.3 (2)C23—C20—C19111.4 (2)
C8B—C7B—C6B116.0 (2)O8—C20—C21109.1 (2)
C7A—C8A—C9A121.4 (3)C23—C20—C21107.0 (2)
C7A—C8A—H8AA119.3C19—C20—C21110.1 (2)
C9A—C8A—H8AA119.3C22—C21—C20117.1 (3)
C7B—C8B—C9B121.6 (3)C22—C21—H21A108.0
C7B—C8B—H8BA119.2C20—C21—H21A108.0
C9B—C8B—H8BA119.2C22—C21—H21B108.0
C8A—C9A—N1A120.8 (3)C20—C21—H21B108.0
C8A—C9A—C4A120.1 (3)H21A—C21—H21B107.3
N1A—C9A—C4A119.2 (2)O7—C22—O6123.3 (3)
C8B—C9B—C4B121.0 (2)O7—C22—C21117.0 (4)
C8B—C9B—N1B119.8 (3)O6—C22—C21119.7 (3)
C4B—C9B—N1B119.1 (2)O9—C23—O10123.5 (3)
N1A—C10A—C11A118.0 (3)O9—C23—C20119.0 (2)
N1A—C10A—C12A119.5 (3)O10—C23—C20117.4 (3)
C11A—C10A—C12A60.6 (2)O11—C24—C25107.4 (6)
N1A—C10A—H10A115.8O11—C24—H24A110.2
C11A—C10A—H10A115.8C25—C24—H24A110.2
C12A—C10A—H10A115.8O11—C24—H24B110.2
N1B—C10B—C12B119.2 (3)C25—C24—H24B110.2
N1B—C10B—C11B119.9 (3)H24A—C24—H24B108.5
C12B—C10B—C11B60.8 (2)C26—C25—C24107.3 (7)
N1B—C10B—H10B115.3C26—C25—H25A110.3
C12B—C10B—H10B115.3C24—C25—H25A110.3
C11B—C10B—H10B115.3C26—C25—H25B110.3
C10A—C11A—C12A59.7 (2)C24—C25—H25B110.3
C10A—C11A—H11A117.8H25A—C25—H25B108.5
C12A—C11A—H11A117.8C27—C26—C25104.1 (7)
C10A—C11A—H11B117.8C27—C26—H26A110.9
C12A—C11A—H11B117.8C25—C26—H26A110.9
H11A—C11A—H11B114.9C27—C26—H26B110.9
C10B—C11B—C12B59.2 (2)C25—C26—H26B110.9
C10B—C11B—H11C117.9H26A—C26—H26B109.0
C12B—C11B—H11C117.9C26—C27—O11108.0 (7)
C10B—C11B—H11D117.9C26—C27—H27A110.1
C12B—C11B—H11D117.9O11—C27—H27A110.1
H11C—C11B—H11D115.0C26—C27—H27B110.1
C10A—C12A—C11A59.7 (2)O11—C27—H27B110.1
C10A—C12A—H12A117.8H27A—C27—H27B108.4
C11A—C12A—H12A117.8

Experimental details

(1)(2)(3)(4)
Crystal data
Chemical formulaC17H19FN3O3·C4H3O4·H2O2(C17H19FN3O3)·C4H2O4·3(H2O)C17H19FN3O3·C4H3O4C6H6O7·2(C17H19FN3O3)·C4H8O·3(H2O)
Mr465.43832.81447.42980.96
Crystal system, space groupTriclinic, P1Monoclinic, P21/nMonoclinic, P21/cTriclinic, P1
Temperature (K)293293293293
a, b, c (Å)9.579 (3), 9.806 (2), 11.612 (4)9.922 (4), 30.199 (9), 13.528 (8)13.956 (4), 10.459 (4), 15.184 (5)10.225 (2), 13.8350 (6), 18.560 (7)
α, β, γ (°)78.66 (2), 89.44 (3), 78.85 (4)90, 109.717 (13), 9090, 108.765 (6), 9072.83 (4), 86.82 (6), 68.03 (5)
V3)1048.8 (5)3816 (3)2098.5 (12)2321.9 (10)
Z2442
Radiation typeCu KαCu KαCu KαCu Kα
µ (mm1)1.020.990.960.96
Crystal size (mm)0.72 × 0.23 × 0.190.43 × 0.12 × 0.030.75 × 0.65 × 0.300.64 × 0.43 × 0.07
Data collection
DiffractometerCCDCCDCCDCCD
Absorption correctionMulti-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
Multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
Multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
Multi-scan
Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan.
Tmin, Tmax0.721, 1.0000.676, 0.9710.707, 1.0000.456, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
15473, 3866, 3412 36407, 7316, 5695 20341, 4083, 3531 23976, 7818, 4946
Rint0.0550.1250.0470.073
(sin θ/λ)max1)0.6090.6180.6180.593
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.124, 1.04 0.082, 0.249, 1.05 0.042, 0.123, 1.04 0.074, 0.218, 1.13
No. of reflections3866731640837818
No. of parameters323588311677
No. of restraints014215
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.30, 0.220.41, 0.560.22, 0.190.71, 0.34

Computer programs: CrystalClear (Rigaku Inc., 2008), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEPII(Johnson,1976)andPLUTON(Spek,1990), SHELXL97(Sheldrick, 1997).

Hydrogen-bond geometry (Å, º) for (1) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O6i0.933 (19)1.968 (19)2.8280 (18)152.3 (15)
N3—H3A···O1ii0.933 (19)2.526 (18)3.0244 (18)113.7 (13)
N3—H3B···O4ii0.99 (2)1.73 (2)2.6752 (17)160.2 (18)
O2—H2A···O30.89 (2)1.73 (3)2.5708 (17)156 (2)
O7—H7A···O80.97 (3)1.60 (3)2.5618 (17)172 (2)
O8—H8B···O5iii0.92 (3)1.83 (3)2.726 (2)165 (2)
O8—H8C···O4iv0.91 (3)1.93 (3)2.833 (2)171 (2)
Symmetry codes: (i) x, y, z+1; (ii) x, y1, z+1; (iii) x, y1, z; (iv) x+1, y, z.
Hydrogen-bond geometry (Å, º) for (3) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O5i0.92 (2)2.25 (2)2.9770 (18)135.7 (18)
N3—H3A···O4i0.92 (2)2.30 (2)3.0317 (18)136.1 (18)
N3—H3A···O2ii0.92 (2)2.43 (2)3.0911 (17)128.4 (18)
N3—H3B···O7iii0.93 (2)1.82 (2)2.7564 (19)175.8 (18)
O2—H2A···O30.96 (3)1.67 (3)2.5521 (17)151 (3)
O4—H4A···O60.830 (10)1.574 (11)2.4039 (17)179 (5)
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x+1, y, z; (iii) x+2, y+1, z+1.
 

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