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Riociguat (Rio) is the first oral soluble guanylate cyclase stimulator to be approved for pulmonary arterial hypertension. In this study, form (II) of riociguat and three solvates with aceto­nitrile [form (III)], N,N-di­methyl­formamide [form (IV)] and ethyl acetate [form (V)] were crystallized. They were identified and characterized by differential scanning calorimetry, thermogravimetric analysis, X-ray powder diffraction, and their crystal structures were determined by single-crystal X-ray diffraction. No crystal structure has previously been reported for the known form (II) of riociguat. Crystal structure determination of Rio and its new solvates revealed that the dimeric R22(14) motif is common in both structures. The crystal packing of solvates adopts channel-like patterns, whereas form (II) of riociguat adopts sheet-like patterns. Strong π–π interactions exist in the above four forms. The conformation of the riociguat in one molecule of 0.5-DMF solvate was found to be significantly different from the conformations found in the other solvates. Desolvation of the three solvates was studied by thermogravimetric analysis and X-ray diffraction, and was shown to transform them into form (I) of riociguat.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617006011/ao5027sup1.cif
Contains datablocks global, II, III, IV, V

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617006011/ao5027IIsup2.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617006011/ao5027IIIsup3.hkl
Contains datablock III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617006011/ao5027IVsup4.hkl
Contains datablock IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2052520617006011/ao5027Vsup5.hkl
Contains datablock V

CCDC references: 1443756; 1443757; 1443758; 1545273

Computing details top

For all structures, data collection: PROCESS-AUTO (Rigaku,2006); cell refinement: PROCESS-AUTO (Rigaku,2006); data reduction: CrystalStructure (Rigaku,2007). Program(s) used to solve structure: SHELXS97 (Sheldrick, 2008) for (II), (III), (IV); SHELXS97 (Sheldrick, 2014) for (V). Program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) for (II), (III), (IV); SHELXL97 (Sheldrick, 2014) for (V). For all structures, molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

(II) top
Crystal data top
C20H19FN8O2Z = 2
Mr = 422.43F(000) = 440
Triclinic, P1Dx = 1.388 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0917 (5) ÅCell parameters from 6412 reflections
b = 10.8937 (6) Åθ = 3.2–27.5°
c = 11.7949 (6) ŵ = 0.10 mm1
α = 88.338 (1)°T = 296 K
β = 82.344 (2)°Chunk, colorless
γ = 78.787 (2)°0.48 × 0.30 × 0.22 mm
V = 1010.76 (10) Å3
Data collection top
Rigaku RAXIS-RAPID/ZJUG
diffractometer
3959 independent reflections
Radiation source: rotating anode2679 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
Detector resolution: 10.00 pixels mm-1θmax = 26.0°, θmin = 3.2°
ω scansh = 99
Absorption correction: multi-scan
Higashi, T. (1995)
k = 1313
Tmin = 0.953, Tmax = 0.978l = 1314
8817 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)] = 0.046H-atom parameters constrained
wR(F2) = 0.143 w = 1/[σ2(Fo2) + (0.0449P)2 + 0.9981P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
3959 reflectionsΔρmax = 0.29 e Å3
283 parametersΔρmin = 0.30 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.086 (5)
Special details top

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

Refinement. 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 > 2sigma(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
C10.6416 (3)0.8715 (2)0.0487 (2)0.0439 (6)
C20.6040 (4)0.8303 (3)0.0516 (2)0.0526 (7)
H20.68090.82590.11810.063*
C30.4500 (4)0.7957 (3)0.0514 (2)0.0599 (8)
H30.42180.76690.11840.072*
C40.3364 (4)0.8034 (3)0.0476 (3)0.0620 (8)
H40.23200.77990.04730.074*
C50.3781 (4)0.8464 (3)0.1475 (2)0.0531 (7)
H50.30110.85130.21400.064*
C60.5319 (3)0.8818 (2)0.1498 (2)0.0412 (6)
C70.5854 (3)0.9304 (3)0.2549 (2)0.0455 (6)
H7A0.69100.87760.27080.055*
H7B0.60711.01410.23920.055*
C80.3434 (3)1.0333 (2)0.4005 (2)0.0402 (6)
C90.1970 (4)1.2272 (3)0.4173 (3)0.0620 (8)
H90.17381.30950.39160.074*
C100.0990 (4)1.1971 (3)0.5178 (3)0.0580 (7)
H100.01541.25840.55580.070*
C110.1266 (3)1.0770 (2)0.5601 (2)0.0461 (6)
H110.06251.05470.62610.055*
C120.2550 (3)0.9900 (2)0.49948 (19)0.0385 (5)
C130.3295 (3)0.8602 (2)0.50550 (19)0.0352 (5)
C140.2862 (3)0.7667 (2)0.59160 (19)0.0370 (5)
C150.1427 (3)0.7264 (2)0.7634 (2)0.0391 (6)
C160.2017 (3)0.5998 (2)0.7461 (2)0.0427 (6)
C170.3084 (4)0.5617 (2)0.6457 (2)0.0477 (7)
C180.2877 (4)0.4684 (3)0.9109 (3)0.0626 (8)
H18A0.24100.41790.97010.094*
H18B0.31390.54040.94430.094*
H18C0.38940.42030.87050.094*
C190.0289 (4)0.4529 (3)0.8334 (2)0.0545 (7)
C200.2189 (5)0.4511 (5)0.7473 (4)0.1053 (15)
H20A0.19190.36140.75020.158*
H20B0.26350.47720.67720.158*
H20C0.30230.48170.81100.158*
F10.7939 (2)0.90673 (16)0.05006 (13)0.0595 (5)
N10.4605 (3)0.93410 (18)0.35544 (16)0.0406 (5)
N20.3193 (3)1.1491 (2)0.35593 (19)0.0516 (6)
N30.4522 (3)0.82834 (18)0.41847 (16)0.0405 (5)
N40.1850 (3)0.81212 (18)0.68472 (16)0.0386 (5)
N50.3524 (3)0.64679 (18)0.56675 (17)0.0455 (5)
N60.0411 (3)0.7716 (2)0.85934 (18)0.0530 (6)
H6A0.00680.85100.86800.064*
H6B0.01080.72100.91180.064*
N70.3715 (4)0.4406 (2)0.6228 (2)0.0787 (10)
H7C0.43710.41940.56010.094*
H7D0.34640.38400.67080.094*
N80.1640 (3)0.5088 (2)0.83140 (18)0.0492 (6)
O10.0017 (3)0.3709 (2)0.90020 (19)0.0736 (7)
O20.0681 (3)0.5005 (2)0.7527 (2)0.0724 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0510 (15)0.0419 (14)0.0378 (13)0.0103 (11)0.0018 (11)0.0062 (11)
C20.071 (2)0.0478 (15)0.0361 (13)0.0081 (14)0.0036 (13)0.0019 (12)
C30.091 (2)0.0520 (17)0.0419 (15)0.0182 (16)0.0203 (15)0.0051 (13)
C40.077 (2)0.0660 (19)0.0549 (17)0.0362 (16)0.0200 (16)0.0078 (15)
C50.0621 (18)0.0597 (17)0.0428 (14)0.0286 (14)0.0028 (13)0.0080 (13)
C60.0541 (15)0.0380 (12)0.0337 (12)0.0165 (11)0.0045 (11)0.0086 (10)
C70.0540 (16)0.0508 (15)0.0343 (12)0.0224 (12)0.0017 (11)0.0072 (11)
C80.0507 (15)0.0400 (13)0.0332 (12)0.0160 (11)0.0082 (11)0.0050 (10)
C90.079 (2)0.0423 (15)0.0658 (19)0.0096 (15)0.0194 (17)0.0121 (14)
C100.0605 (18)0.0460 (15)0.0643 (18)0.0007 (13)0.0110 (15)0.0009 (14)
C110.0463 (15)0.0488 (15)0.0433 (14)0.0099 (12)0.0059 (12)0.0013 (12)
C120.0430 (14)0.0406 (13)0.0338 (12)0.0129 (10)0.0052 (10)0.0013 (10)
C130.0414 (13)0.0348 (12)0.0304 (11)0.0115 (10)0.0028 (10)0.0023 (9)
C140.0401 (13)0.0369 (12)0.0334 (12)0.0114 (10)0.0028 (10)0.0017 (10)
C150.0367 (13)0.0450 (13)0.0340 (12)0.0096 (10)0.0036 (10)0.0034 (10)
C160.0481 (15)0.0388 (13)0.0380 (13)0.0128 (11)0.0109 (11)0.0050 (10)
C170.0554 (16)0.0393 (13)0.0452 (14)0.0153 (12)0.0145 (12)0.0002 (11)
C180.0609 (19)0.0634 (19)0.0574 (17)0.0047 (15)0.0000 (15)0.0166 (15)
C190.0574 (17)0.0488 (15)0.0519 (16)0.0123 (13)0.0132 (14)0.0103 (13)
C200.088 (3)0.136 (4)0.111 (3)0.070 (3)0.018 (3)0.028 (3)
F10.0505 (10)0.0751 (11)0.0509 (9)0.0156 (8)0.0053 (7)0.0022 (8)
N10.0551 (13)0.0389 (11)0.0298 (10)0.0195 (10)0.0012 (9)0.0058 (8)
N20.0709 (16)0.0405 (12)0.0461 (12)0.0154 (11)0.0131 (11)0.0115 (10)
N30.0511 (12)0.0379 (11)0.0331 (10)0.0151 (9)0.0016 (9)0.0049 (8)
N40.0425 (11)0.0377 (10)0.0336 (10)0.0087 (9)0.0034 (9)0.0030 (8)
N50.0577 (14)0.0356 (11)0.0407 (11)0.0169 (10)0.0139 (10)0.0010 (9)
N60.0623 (15)0.0479 (13)0.0399 (12)0.0051 (11)0.0171 (11)0.0027 (10)
N70.112 (2)0.0345 (12)0.0717 (17)0.0122 (13)0.0496 (16)0.0024 (12)
N80.0493 (13)0.0476 (12)0.0461 (12)0.0104 (10)0.0092 (10)0.0132 (10)
O10.0830 (16)0.0598 (13)0.0751 (14)0.0266 (11)0.0134 (12)0.0262 (11)
O20.0666 (14)0.0824 (15)0.0765 (15)0.0372 (12)0.0122 (12)0.0310 (13)
Geometric parameters (Å, º) top
C1—F11.362 (3)C13—C141.475 (3)
C1—C21.369 (4)C14—N41.325 (3)
C1—C61.382 (3)C14—N51.337 (3)
C2—C31.369 (4)C15—N61.351 (3)
C2—H20.9300C15—N41.357 (3)
C3—C41.381 (4)C15—C161.380 (3)
C3—H30.9300C16—C171.392 (3)
C4—C51.386 (4)C16—N81.438 (3)
C4—H40.9300C17—N71.340 (3)
C5—C61.376 (4)C17—N51.357 (3)
C5—H50.9300C18—N81.459 (4)
C6—C71.508 (3)C18—H18A0.9600
C7—N11.448 (3)C18—H18B0.9600
C7—H7A0.9700C18—H18C0.9600
C7—H7B0.9700C19—O11.214 (3)
C8—N21.342 (3)C19—O21.343 (4)
C8—N11.360 (3)C19—N81.348 (4)
C8—C121.405 (3)C20—O21.435 (4)
C9—N21.320 (4)C20—H20A0.9600
C9—C101.404 (4)C20—H20B0.9600
C9—H90.9300C20—H20C0.9600
C10—C111.374 (4)N1—N31.361 (3)
C10—H100.9300N6—H6A0.8600
C11—C121.396 (4)N6—H6B0.8600
C11—H110.9300N7—H7C0.8600
C12—C131.429 (3)N7—H7D0.8600
C13—N31.332 (3)
F1—C1—C2119.0 (2)N4—C14—C13115.7 (2)
F1—C1—C6117.4 (2)N5—C14—C13116.6 (2)
C2—C1—C6123.6 (3)N6—C15—N4116.5 (2)
C3—C2—C1118.2 (3)N6—C15—C16122.1 (2)
C3—C2—H2120.9N4—C15—C16121.4 (2)
C1—C2—H2120.9C15—C16—C17118.2 (2)
C2—C3—C4120.4 (3)C15—C16—N8121.8 (2)
C2—C3—H3119.8C17—C16—N8119.9 (2)
C4—C3—H3119.8N7—C17—N5117.4 (2)
C3—C4—C5119.9 (3)N7—C17—C16121.8 (2)
C3—C4—H4120.0N5—C17—C16120.8 (2)
C5—C4—H4120.0N8—C18—H18A109.5
C6—C5—C4120.9 (3)N8—C18—H18B109.5
C6—C5—H5119.5H18A—C18—H18B109.5
C4—C5—H5119.5N8—C18—H18C109.5
C5—C6—C1117.0 (2)H18A—C18—H18C109.5
C5—C6—C7123.9 (2)H18B—C18—H18C109.5
C1—C6—C7119.1 (2)O1—C19—O2124.4 (3)
N1—C7—C6113.6 (2)O1—C19—N8124.3 (3)
N1—C7—H7A108.8O2—C19—N8111.3 (2)
C6—C7—H7A108.8O2—C20—H20A109.5
N1—C7—H7B108.8O2—C20—H20B109.5
C6—C7—H7B108.8H20A—C20—H20B109.5
H7A—C7—H7B107.7O2—C20—H20C109.5
N2—C8—N1125.2 (2)H20A—C20—H20C109.5
N2—C8—C12127.9 (2)H20B—C20—H20C109.5
N1—C8—C12106.9 (2)C8—N1—N3111.57 (18)
N2—C9—C10125.9 (3)C8—N1—C7128.6 (2)
N2—C9—H9117.1N3—N1—C7119.8 (2)
C10—C9—H9117.1C9—N2—C8112.4 (2)
C11—C10—C9119.9 (3)C13—N3—N1106.47 (19)
C11—C10—H10120.0C14—N4—C15115.9 (2)
C9—C10—H10120.0C14—N5—C17116.0 (2)
C10—C11—C12117.1 (2)C15—N6—H6A120.0
C10—C11—H11121.5C15—N6—H6B120.0
C12—C11—H11121.5H6A—N6—H6B120.0
C11—C12—C8116.8 (2)C17—N7—H7C120.0
C11—C12—C13138.8 (2)C17—N7—H7D120.0
C8—C12—C13104.4 (2)H7C—N7—H7D120.0
N3—C13—C12110.63 (19)C19—N8—C16122.5 (2)
N3—C13—C14120.9 (2)C19—N8—C18119.9 (2)
C12—C13—C14128.5 (2)C16—N8—C18117.4 (2)
N4—C14—N5127.7 (2)C19—O2—C20117.0 (3)
F1—C1—C2—C3179.7 (2)N8—C16—C17—N73.5 (5)
C6—C1—C2—C31.0 (4)C15—C16—C17—N50.4 (4)
C1—C2—C3—C40.4 (4)N8—C16—C17—N5176.6 (2)
C2—C3—C4—C50.0 (5)N2—C8—N1—N3178.6 (2)
C3—C4—C5—C60.1 (5)C12—C8—N1—N30.8 (3)
C4—C5—C6—C10.5 (4)N2—C8—N1—C72.0 (4)
C4—C5—C6—C7179.5 (3)C12—C8—N1—C7178.6 (2)
F1—C1—C6—C5179.8 (2)C6—C7—N1—C898.7 (3)
C2—C1—C6—C51.0 (4)C6—C7—N1—N382.0 (3)
F1—C1—C6—C70.2 (3)C10—C9—N2—C80.4 (4)
C2—C1—C6—C7179.0 (2)N1—C8—N2—C9180.0 (3)
C5—C6—C7—N11.2 (4)C12—C8—N2—C90.7 (4)
C1—C6—C7—N1178.8 (2)C12—C13—N3—N10.2 (3)
N2—C9—C10—C110.2 (5)C14—C13—N3—N1180.0 (2)
C9—C10—C11—C120.6 (4)C8—N1—N3—C130.6 (3)
C10—C11—C12—C80.3 (4)C7—N1—N3—C13178.9 (2)
C10—C11—C12—C13179.0 (3)N5—C14—N4—C150.6 (4)
N2—C8—C12—C110.3 (4)C13—C14—N4—C15179.0 (2)
N1—C8—C12—C11179.7 (2)N6—C15—N4—C14179.3 (2)
N2—C8—C12—C13178.8 (2)C16—C15—N4—C140.4 (4)
N1—C8—C12—C130.6 (3)N4—C14—N5—C171.1 (4)
C11—C12—C13—N3179.1 (3)C13—C14—N5—C17178.6 (2)
C8—C12—C13—N30.3 (3)N7—C17—N5—C14179.4 (3)
C11—C12—C13—C140.7 (5)C16—C17—N5—C140.5 (4)
C8—C12—C13—C14179.5 (2)O1—C19—N8—C16175.8 (3)
N3—C13—C14—N4168.3 (2)O2—C19—N8—C164.7 (4)
C12—C13—C14—N411.9 (4)O1—C19—N8—C182.0 (4)
N3—C13—C14—N512.0 (3)O2—C19—N8—C18178.6 (2)
C12—C13—C14—N5167.8 (2)C15—C16—N8—C1992.4 (3)
N6—C15—C16—C17178.8 (3)C17—C16—N8—C1991.4 (3)
N4—C15—C16—C170.8 (4)C15—C16—N8—C1893.5 (3)
N6—C15—C16—N82.6 (4)C17—C16—N8—C1882.6 (3)
N4—C15—C16—N8177.0 (2)O1—C19—O2—C200.9 (5)
C15—C16—C17—N7179.7 (3)N8—C19—O2—C20178.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N7—H7C···N5i0.862.142.977 (3)165
Symmetry code: (i) x+1, y+1, z+1.
(III) top
Crystal data top
C20H19FN8O2·C2H3NZ = 2
Mr = 463.49F(000) = 484
Triclinic, P1Dx = 1.308 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.4657 (5) ÅCell parameters from 6092 reflections
b = 11.4408 (8) Åθ = 3.0–27.4°
c = 13.1812 (9) ŵ = 0.10 mm1
α = 112.419 (2)°T = 296 K
β = 90.914 (3)°Chunk, colorless
γ = 93.446 (2)°0.42 × 0.36 × 0.30 mm
V = 1176.99 (13) Å3
Data collection top
Rigaku RAXIS-RAPID/ZJUG
diffractometer
4151 independent reflections
Radiation source: rotating anode2576 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
Detector resolution: 10.00 pixels mm-1θmax = 25.0°, θmin = 3.0°
ω scansh = 108
Absorption correction: multi-scan
Higashi, T. (1995)
k = 1313
Tmin = 0.951, Tmax = 0.972l = 1515
9234 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)] = 0.054H-atom parameters constrained
wR(F2) = 0.160 w = 1/[σ2(Fo2) + (0.0598P)2 + 0.7424P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
4151 reflectionsΔρmax = 0.46 e Å3
310 parametersΔρmin = 0.29 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.075 (5)
Special details top

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

Refinement. 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 > 2sigma(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
C10.5906 (4)0.1716 (3)0.0115 (2)0.0682 (9)
C20.6798 (5)0.0812 (4)0.0608 (3)0.0877 (12)
H20.67500.06640.13530.105*
C30.7763 (5)0.0128 (4)0.0217 (3)0.0904 (12)
H30.83690.04800.06970.108*
C40.7820 (4)0.0354 (3)0.0886 (3)0.0808 (10)
H40.84730.00980.11540.097*
C50.6900 (4)0.1261 (3)0.1604 (2)0.0657 (8)
H50.69410.14000.23470.079*
C60.5918 (3)0.1966 (3)0.1229 (2)0.0555 (7)
C70.4882 (4)0.2988 (3)0.1951 (2)0.0628 (8)
H7A0.53140.38090.19880.075*
H7B0.38270.28400.16080.075*
C80.3445 (3)0.2665 (3)0.3518 (2)0.0509 (7)
C90.0915 (4)0.1932 (3)0.3654 (3)0.0739 (10)
H90.00850.15830.33460.089*
C100.1201 (4)0.2202 (3)0.4771 (3)0.0733 (9)
H100.04010.20400.51840.088*
C110.2700 (3)0.2719 (3)0.5269 (2)0.0613 (8)
H110.29020.28940.60100.074*
C120.3896 (3)0.2968 (3)0.46272 (19)0.0482 (7)
C130.5534 (3)0.3514 (2)0.47514 (19)0.0481 (7)
C140.6653 (3)0.3991 (2)0.57354 (19)0.0474 (7)
C150.7094 (4)0.4292 (3)0.7535 (2)0.0549 (7)
C160.8677 (3)0.4771 (3)0.74990 (19)0.0507 (7)
C170.9173 (3)0.4866 (2)0.65239 (19)0.0467 (6)
C180.9902 (5)0.6538 (3)0.9138 (2)0.0842 (11)
H18A1.06890.67040.97180.126*
H18B0.88920.67650.94490.126*
H18C1.01870.70310.87120.126*
C191.0931 (4)0.4439 (4)0.8565 (2)0.0673 (9)
C201.1770 (6)0.2355 (5)0.7921 (3)0.1103 (15)
H20A1.14820.15270.73750.166*
H20B1.17430.23220.86380.166*
H20C1.28190.26310.78020.166*
C210.7068 (7)0.0664 (5)0.5111 (6)0.134 (2)
C220.6968 (9)0.0894 (5)0.6310 (5)0.164 (3)
H22A0.59440.05840.64410.246*
H22B0.71250.17870.67400.246*
H22C0.77720.04590.65150.246*
F10.4935 (3)0.2395 (2)0.02641 (14)0.0997 (7)
N10.4762 (3)0.3026 (2)0.30596 (16)0.0567 (6)
N20.2006 (3)0.2147 (2)0.29956 (19)0.0637 (7)
N30.6034 (3)0.3550 (2)0.38040 (16)0.0543 (6)
N40.6040 (3)0.3893 (2)0.66409 (16)0.0548 (6)
N50.8142 (3)0.4460 (2)0.56229 (16)0.0486 (6)
N60.6498 (3)0.4182 (3)0.84490 (19)0.0819 (9)
H6A0.55370.38830.84340.098*
H6B0.70820.44110.90420.098*
N71.0661 (3)0.5347 (2)0.64376 (18)0.0616 (7)
H7C1.09350.53920.58270.074*
H7D1.13220.56050.69940.074*
N80.9805 (3)0.5196 (2)0.84349 (17)0.0609 (7)
N90.7051 (9)0.0442 (6)0.4170 (5)0.190 (3)
O11.2058 (3)0.4791 (3)0.92485 (19)0.0973 (9)
O21.0656 (3)0.3241 (2)0.78450 (17)0.0760 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0627 (19)0.093 (2)0.0381 (16)0.0059 (17)0.0049 (14)0.0150 (16)
C20.082 (2)0.111 (3)0.0412 (18)0.013 (2)0.0086 (17)0.0006 (19)
C30.074 (2)0.083 (3)0.075 (3)0.005 (2)0.013 (2)0.012 (2)
C40.066 (2)0.075 (2)0.084 (3)0.0084 (18)0.0007 (18)0.011 (2)
C50.0632 (19)0.074 (2)0.0512 (17)0.0060 (16)0.0029 (14)0.0141 (16)
C60.0497 (16)0.0708 (19)0.0336 (14)0.0033 (14)0.0063 (12)0.0077 (13)
C70.0645 (18)0.088 (2)0.0317 (14)0.0147 (17)0.0063 (12)0.0178 (14)
C80.0512 (16)0.0549 (17)0.0366 (14)0.0144 (13)0.0040 (12)0.0051 (12)
C90.0526 (18)0.094 (3)0.063 (2)0.0055 (17)0.0080 (16)0.0161 (18)
C100.0565 (19)0.095 (3)0.064 (2)0.0040 (18)0.0034 (15)0.0263 (19)
C110.0646 (19)0.072 (2)0.0425 (15)0.0108 (16)0.0025 (14)0.0159 (14)
C120.0559 (16)0.0509 (16)0.0312 (13)0.0128 (13)0.0031 (11)0.0071 (12)
C130.0591 (17)0.0509 (16)0.0293 (13)0.0089 (13)0.0040 (11)0.0092 (11)
C140.0619 (17)0.0439 (15)0.0318 (13)0.0059 (13)0.0068 (12)0.0094 (11)
C150.077 (2)0.0543 (17)0.0322 (14)0.0103 (15)0.0095 (13)0.0179 (12)
C160.0720 (19)0.0499 (16)0.0281 (13)0.0066 (14)0.0125 (12)0.0146 (12)
C170.0602 (17)0.0440 (15)0.0335 (13)0.0001 (13)0.0069 (11)0.0130 (11)
C180.127 (3)0.069 (2)0.0438 (17)0.028 (2)0.0169 (18)0.0139 (16)
C190.076 (2)0.093 (3)0.0414 (16)0.0160 (19)0.0139 (15)0.0388 (18)
C200.137 (4)0.129 (4)0.083 (3)0.049 (3)0.002 (2)0.055 (3)
C210.138 (5)0.080 (3)0.183 (6)0.002 (3)0.009 (5)0.049 (4)
C220.282 (8)0.099 (4)0.106 (4)0.035 (5)0.005 (5)0.029 (3)
F10.1128 (16)0.143 (2)0.0474 (11)0.0136 (15)0.0110 (10)0.0412 (12)
N10.0552 (14)0.0782 (17)0.0290 (11)0.0075 (12)0.0081 (10)0.0119 (11)
N20.0543 (14)0.0769 (18)0.0465 (13)0.0109 (13)0.0083 (12)0.0083 (12)
N30.0594 (14)0.0662 (15)0.0317 (11)0.0049 (12)0.0080 (10)0.0128 (11)
N40.0703 (15)0.0601 (15)0.0310 (11)0.0083 (12)0.0078 (10)0.0164 (10)
N50.0593 (14)0.0518 (13)0.0315 (11)0.0044 (11)0.0076 (10)0.0129 (10)
N60.092 (2)0.116 (2)0.0375 (13)0.0418 (17)0.0178 (13)0.0373 (15)
N70.0672 (16)0.0801 (18)0.0359 (12)0.0107 (13)0.0118 (11)0.0234 (12)
N80.0825 (17)0.0607 (15)0.0365 (12)0.0162 (13)0.0186 (11)0.0192 (11)
N90.274 (8)0.155 (5)0.161 (5)0.041 (5)0.072 (6)0.075 (5)
O10.0976 (18)0.139 (2)0.0609 (14)0.0233 (16)0.0388 (13)0.0502 (15)
O20.0936 (17)0.0793 (16)0.0575 (13)0.0077 (13)0.0177 (12)0.0296 (12)
Geometric parameters (Å, º) top
C1—F11.374 (4)C14—N51.372 (3)
C1—C21.384 (5)C15—N61.360 (3)
C1—C61.384 (4)C15—N41.378 (3)
C2—C31.384 (5)C15—C161.425 (4)
C2—H20.9300C16—C171.400 (4)
C3—C41.375 (5)C16—N81.456 (3)
C3—H30.9300C17—N71.368 (3)
C4—C51.397 (4)C17—N51.373 (3)
C4—H40.9300C18—N81.456 (4)
C5—C61.399 (4)C18—H18A0.9600
C5—H50.9300C18—H18B0.9600
C6—C71.531 (4)C18—H18C0.9600
C7—N11.451 (3)C19—O11.238 (3)
C7—H7A0.9700C19—O21.340 (4)
C7—H7B0.9700C19—N81.376 (4)
C8—N21.373 (3)C20—O21.455 (4)
C8—N11.391 (4)C20—H20A0.9600
C8—C121.408 (3)C20—H20B0.9600
C9—N21.352 (4)C20—H20C0.9600
C9—C101.398 (4)C21—N91.167 (7)
C9—H90.9300C21—C221.505 (7)
C10—C111.406 (4)C22—H22A0.9600
C10—H100.9300C22—H22B0.9600
C11—C121.413 (4)C22—H22C0.9600
C11—H110.9300N1—N31.386 (3)
C12—C131.466 (4)N6—H6A0.8600
C13—N31.340 (3)N6—H6B0.8600
C13—C141.496 (3)N7—H7C0.8600
C14—N41.350 (3)N7—H7D0.8600
F1—C1—C2120.2 (3)N4—C15—C16122.7 (2)
F1—C1—C6117.1 (3)C17—C16—C15118.7 (2)
C2—C1—C6122.7 (3)C17—C16—N8117.8 (3)
C3—C2—C1119.6 (3)C15—C16—N8123.4 (2)
C3—C2—H2120.2N7—C17—N5118.8 (2)
C1—C2—H2120.2N7—C17—C16122.0 (2)
C4—C3—C2119.6 (3)N5—C17—C16119.2 (3)
C4—C3—H3120.2N8—C18—H18A109.5
C2—C3—H3120.2N8—C18—H18B109.5
C3—C4—C5120.1 (4)H18A—C18—H18B109.5
C3—C4—H4119.9N8—C18—H18C109.5
C5—C4—H4119.9H18A—C18—H18C109.5
C4—C5—C6121.3 (3)H18B—C18—H18C109.5
C4—C5—H5119.3O1—C19—O2123.2 (3)
C6—C5—H5119.3O1—C19—N8125.8 (3)
C1—C6—C5116.7 (3)O2—C19—N8111.0 (2)
C1—C6—C7118.1 (3)O2—C20—H20A109.5
C5—C6—C7125.2 (2)O2—C20—H20B109.5
N1—C7—C6113.7 (2)H20A—C20—H20B109.5
N1—C7—H7A108.8O2—C20—H20C109.5
C6—C7—H7A108.8H20A—C20—H20C109.5
N1—C7—H7B108.8H20B—C20—H20C109.5
C6—C7—H7B108.8N9—C21—C22175.6 (8)
H7A—C7—H7B107.7C21—C22—H22A109.5
N2—C8—N1126.8 (2)C21—C22—H22B109.5
N2—C8—C12127.8 (3)H22A—C22—H22B109.5
N1—C8—C12105.4 (2)C21—C22—H22C109.5
N2—C9—C10123.8 (3)H22A—C22—H22C109.5
N2—C9—H9118.1H22B—C22—H22C109.5
C10—C9—H9118.1N3—N1—C8113.4 (2)
C9—C10—C11120.0 (3)N3—N1—C7119.1 (2)
C9—C10—H10120.0C8—N1—C7127.4 (2)
C11—C10—H10120.0C9—N2—C8114.2 (2)
C10—C11—C12119.1 (3)C13—N3—N1104.9 (2)
C10—C11—H11120.5C14—N4—C15113.7 (2)
C12—C11—H11120.5C14—N5—C17117.5 (2)
C8—C12—C11115.1 (3)C15—N6—H6A120.0
C8—C12—C13105.1 (2)C15—N6—H6B120.0
C11—C12—C13139.7 (2)H6A—N6—H6B120.0
N3—C13—C12111.2 (2)C17—N7—H7C120.0
N3—C13—C14118.7 (2)C17—N7—H7D120.0
C12—C13—C14130.1 (2)H7C—N7—H7D120.0
N4—C14—N5128.1 (2)C19—N8—C18119.4 (3)
N4—C14—C13113.9 (2)C19—N8—C16122.5 (2)
N5—C14—C13118.0 (2)C18—N8—C16117.2 (2)
N6—C15—N4114.3 (3)C19—O2—C20115.5 (3)
N6—C15—C16123.0 (2)
F1—C1—C2—C3179.6 (3)N8—C16—C17—N70.4 (4)
C6—C1—C2—C30.7 (5)C15—C16—C17—N52.0 (4)
C1—C2—C3—C40.1 (6)N8—C16—C17—N5179.4 (2)
C2—C3—C4—C50.5 (6)N2—C8—N1—N3178.5 (2)
C3—C4—C5—C60.6 (5)C12—C8—N1—N30.3 (3)
F1—C1—C6—C5179.5 (3)N2—C8—N1—C73.0 (5)
C2—C1—C6—C50.6 (5)C12—C8—N1—C7175.8 (3)
F1—C1—C6—C71.1 (4)C6—C7—N1—N375.5 (3)
C2—C1—C6—C7180.0 (3)C6—C7—N1—C8109.3 (3)
C4—C5—C6—C10.1 (5)C10—C9—N2—C80.1 (5)
C4—C5—C6—C7179.3 (3)N1—C8—N2—C9177.6 (3)
C1—C6—C7—N1169.9 (3)C12—C8—N2—C91.0 (4)
C5—C6—C7—N110.8 (4)C12—C13—N3—N10.7 (3)
N2—C9—C10—C110.6 (5)C14—C13—N3—N1178.7 (2)
C9—C10—C11—C120.6 (5)C8—N1—N3—C130.6 (3)
N2—C8—C12—C111.0 (4)C7—N1—N3—C13176.5 (2)
N1—C8—C12—C11177.8 (2)N5—C14—N4—C151.9 (4)
N2—C8—C12—C13178.9 (3)C13—C14—N4—C15177.8 (2)
N1—C8—C12—C130.1 (3)N6—C15—N4—C14179.1 (2)
C10—C11—C12—C80.1 (4)C16—C15—N4—C140.4 (4)
C10—C11—C12—C13177.0 (3)N4—C14—N5—C171.4 (4)
C8—C12—C13—N30.5 (3)C13—C14—N5—C17178.3 (2)
C11—C12—C13—N3176.6 (3)N7—C17—N5—C14179.5 (2)
C8—C12—C13—C14178.8 (3)C16—C17—N5—C140.7 (4)
C11—C12—C13—C144.2 (5)O1—C19—N8—C180.4 (5)
N3—C13—C14—N4179.0 (2)O2—C19—N8—C18179.6 (3)
C12—C13—C14—N40.2 (4)O1—C19—N8—C16169.3 (3)
N3—C13—C14—N50.7 (4)O2—C19—N8—C1610.8 (4)
C12—C13—C14—N5180.0 (2)C17—C16—N8—C1983.2 (3)
N6—C15—C16—C17179.1 (3)C15—C16—N8—C1998.2 (3)
N4—C15—C16—C171.4 (4)C17—C16—N8—C1885.9 (3)
N6—C15—C16—N80.5 (5)C15—C16—N8—C1892.7 (3)
N4—C15—C16—N8180.0 (3)O1—C19—O2—C200.7 (5)
C15—C16—C17—N7178.2 (3)N8—C19—O2—C20179.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6—H6B···O1i0.862.183.012 (3)164
N7—H7C···N5ii0.862.142.995 (3)174
Symmetry codes: (i) x+2, y+1, z+2; (ii) x+2, y+1, z+1.
(IV) top
Crystal data top
2(C20H19FN8O2)·C3H7NOZ = 2
Mr = 917.94F(000) = 960
Triclinic, P1Dx = 1.359 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.6703 (7) ÅCell parameters from 10475 reflections
b = 13.4220 (9) Åθ = 3.1–27.4°
c = 16.9095 (12) ŵ = 0.10 mm1
α = 73.920 (3)°T = 296 K
β = 74.788 (2)°Chunk, colorless
γ = 83.294 (2)°0.36 × 0.20 × 0.16 mm
V = 2242.9 (3) Å3
Data collection top
Rigaku RAXIS-RAPID/ZJUG
diffractometer
7763 independent reflections
Radiation source: rotating anode3928 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.057
Detector resolution: 10.00 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω scansh = 1212
Absorption correction: multi-scan
Higashi, T. (1995)
k = 1515
Tmin = 0.965, Tmax = 0.984l = 1720
17506 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)] = 0.085H-atom parameters constrained
wR(F2) = 0.231 w = 1/[σ2(Fo2) + (0.0932P)2 + 2.0768P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
7763 reflectionsΔρmax = 0.52 e Å3
604 parametersΔρmin = 0.43 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0094 (16)
Special details top

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

Refinement. 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 > 2sigma(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
C1A0.6582 (8)0.9293 (7)0.6363 (6)0.129 (3)
C1B0.2536 (5)0.2261 (5)0.8555 (4)0.0778 (16)
C1C0.2173 (6)0.7487 (5)0.5421 (5)0.0874 (18)
H1C0.26170.70480.57990.105*
C2A0.7052 (9)0.9547 (9)0.6921 (8)0.159 (2)
H2A0.72121.02340.68600.191*
C2B0.2716 (6)0.2163 (6)0.7814 (5)0.102 (2)
H2B0.29520.15350.77770.123*
C2C0.0199 (7)0.7044 (7)0.6500 (5)0.129 (3)
H2C10.04420.66470.64350.194*
H2C20.02250.75350.68160.194*
H2C30.07810.65870.67990.194*
C3A0.7297 (8)0.8795 (9)0.7582 (6)0.136 (2)
H3A0.76390.89600.79800.163*
C3B0.2546 (6)0.2995 (7)0.7128 (5)0.101 (2)
H3B0.26710.29450.66170.121*
C3C0.0211 (7)0.8311 (6)0.5128 (6)0.137 (3)
H3C10.07620.85070.45670.206*
H3C20.00620.89170.53370.206*
H3C30.05380.79900.51150.206*
C4A0.7033 (8)0.7732 (8)0.7678 (6)0.144 (3)
H4A0.71830.72090.81400.172*
C4B0.2191 (5)0.3906 (6)0.7196 (4)0.0865 (18)
H4B0.20610.44760.67260.104*
C5A0.6545 (6)0.7510 (8)0.7057 (6)0.114 (2)
H5A0.63790.68310.70960.137*
C5B0.2023 (4)0.3988 (4)0.7953 (3)0.0661 (13)
H5B0.17890.46170.79890.079*
C6A0.6313 (5)0.8311 (5)0.6382 (5)0.088 (2)
C6B0.2193 (4)0.3167 (4)0.8654 (3)0.0538 (12)
C7A0.5794 (5)0.8165 (4)0.5698 (4)0.0816 (18)
H7A10.48990.84370.57710.098*
H7A20.62880.85650.51590.098*
C7B0.2012 (5)0.3173 (4)0.9509 (3)0.0650 (14)
H7B10.27120.28070.99460.078*
H7B20.12020.27950.95850.078*
C8A0.6811 (4)0.6556 (3)0.5254 (3)0.0514 (11)
C8B0.2901 (4)0.4689 (3)1.0135 (3)0.0491 (11)
C9A0.8724 (5)0.6235 (5)0.4435 (3)0.0743 (15)
H9A0.95330.64420.40900.089*
C9B0.4704 (5)0.4929 (5)1.1092 (3)0.0731 (15)
H9B0.54930.47061.14590.088*
C10A0.8435 (5)0.5209 (4)0.4575 (3)0.0742 (15)
H10A0.90360.47680.43130.089*
C10B0.4340 (5)0.5904 (4)1.1052 (3)0.0716 (15)
H10B0.48810.63031.13870.086*
C11A0.7281 (4)0.4840 (4)0.5092 (3)0.0599 (13)
H11A0.70780.41530.51920.072*
C11B0.3193 (4)0.6284 (4)1.0526 (3)0.0604 (13)
H11B0.29410.69371.04940.072*
C12A0.6427 (4)0.5536 (3)0.5459 (3)0.0459 (10)
C12B0.2418 (4)0.5655 (3)1.0038 (3)0.0467 (11)
C13A0.5180 (4)0.5542 (3)0.6042 (3)0.0457 (10)
C13B0.1190 (4)0.5663 (3)0.9448 (3)0.0439 (10)
C14A0.4356 (4)0.4661 (3)0.6501 (3)0.0427 (10)
C14B0.0247 (4)0.6482 (3)0.9089 (3)0.0449 (10)
C15A0.4101 (4)0.2933 (3)0.6748 (3)0.0458 (10)
C15B0.0324 (4)0.8098 (3)0.8999 (3)0.0545 (12)
C16A0.2978 (4)0.3016 (3)0.7367 (3)0.0465 (11)
C16B0.1452 (4)0.7965 (3)0.8404 (3)0.0560 (12)
C17A0.2564 (4)0.3999 (3)0.7493 (3)0.0484 (11)
C17B0.1676 (4)0.7027 (3)0.8182 (3)0.0517 (11)
C18A0.1051 (4)0.2001 (4)0.7588 (3)0.0678 (14)
H18A0.06360.13890.79630.102*
H18B0.13010.19240.70180.102*
H18C0.04580.25930.76110.102*
C18B0.3469 (5)0.8659 (4)0.8473 (3)0.0681 (14)
H18D0.40980.91650.81460.102*
H18E0.38800.79760.85340.102*
H18F0.31130.87810.90230.102*
C19A0.2472 (4)0.1474 (3)0.8542 (3)0.0545 (12)
C19B0.2437 (6)0.9420 (4)0.7331 (4)0.0789 (17)
C20A0.3939 (6)0.0996 (5)0.9424 (4)0.100 (2)
H20A0.31730.08520.98800.149*
H20B0.45450.13270.95870.149*
H20C0.43310.03580.93010.149*
C20B0.1348 (9)1.0015 (6)0.6209 (5)0.149 (3)
H20D0.13591.07270.62160.224*
H20E0.05600.99070.60780.224*
H20F0.20820.98540.57870.224*
F1A0.6286 (7)1.0075 (4)0.5705 (5)0.215 (3)
F1B0.2708 (4)0.1430 (3)0.9239 (3)0.1223 (14)
N1A0.5835 (3)0.7095 (3)0.5670 (3)0.0618 (11)
N1B0.1989 (4)0.4201 (3)0.9623 (2)0.0546 (10)
N1C0.0920 (4)0.7590 (4)0.5679 (3)0.0811 (13)
N2A0.7939 (4)0.6944 (3)0.4755 (3)0.0689 (12)
N2B0.4012 (4)0.4286 (3)1.0644 (2)0.0638 (11)
N3A0.4853 (3)0.6472 (3)0.6160 (2)0.0575 (10)
N3B0.0948 (3)0.4789 (3)0.9212 (2)0.0545 (10)
N4A0.4812 (3)0.3774 (3)0.6310 (2)0.0478 (9)
N4B0.0545 (3)0.7339 (3)0.9361 (2)0.0511 (9)
N5A0.3263 (3)0.4840 (3)0.7054 (2)0.0466 (9)
N5B0.0823 (3)0.6265 (3)0.8527 (2)0.0481 (9)
N6A0.4565 (3)0.2042 (3)0.6546 (2)0.0623 (11)
H6A10.52720.20290.61600.075*
H6A20.41570.14820.68030.075*
N6B0.0041 (4)0.8980 (3)0.9263 (3)0.0763 (14)
H6B10.06600.90400.96420.092*
H6B20.05630.94810.90520.092*
N7A0.1448 (3)0.4165 (3)0.8046 (2)0.0614 (11)
H7A30.12150.47810.81040.074*
H7A40.09670.36540.83420.074*
N7B0.2739 (4)0.6835 (3)0.7604 (2)0.0678 (12)
H7B30.28480.62510.74720.081*
H7B40.33130.72950.73650.081*
N8A0.2201 (3)0.2146 (3)0.7846 (2)0.0507 (9)
N8B0.2422 (4)0.8743 (3)0.8040 (3)0.0707 (13)
O1A0.1783 (3)0.0763 (2)0.9001 (2)0.0676 (10)
O1B0.3286 (4)1.0048 (3)0.6990 (3)0.1186 (18)
O1C0.2814 (5)0.7915 (4)0.4729 (4)0.1256 (18)
O2A0.3589 (3)0.1671 (2)0.8682 (2)0.0651 (9)
O2B0.1413 (4)0.9356 (3)0.7022 (3)0.0907 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.141 (7)0.083 (6)0.148 (8)0.043 (5)0.037 (6)0.059 (5)
C1B0.087 (4)0.079 (4)0.077 (4)0.026 (3)0.008 (3)0.037 (3)
C1C0.068 (4)0.079 (4)0.113 (5)0.003 (3)0.000 (3)0.044 (4)
C2A0.167 (7)0.1640.1710.0650.008 (6)0.104 (5)
C2B0.113 (5)0.116 (6)0.103 (6)0.026 (4)0.026 (4)0.062 (5)
C2C0.096 (5)0.179 (8)0.106 (6)0.022 (5)0.008 (4)0.051 (6)
C3A0.141 (7)0.1700.1320.0070.040 (5)0.094 (4)
C3B0.092 (4)0.151 (7)0.086 (5)0.004 (4)0.033 (4)0.064 (5)
C3C0.123 (6)0.108 (6)0.194 (9)0.005 (5)0.075 (6)0.024 (6)
C4A0.134 (7)0.151 (9)0.1580.025 (6)0.034 (6)0.075 (6)
C4B0.081 (4)0.118 (6)0.071 (4)0.004 (3)0.030 (3)0.033 (4)
C5A0.091 (5)0.151 (8)0.117 (6)0.001 (5)0.024 (4)0.066 (6)
C5B0.067 (3)0.071 (4)0.063 (3)0.004 (3)0.014 (2)0.023 (3)
C6A0.060 (3)0.074 (4)0.128 (6)0.022 (3)0.023 (4)0.058 (4)
C6B0.051 (3)0.060 (3)0.056 (3)0.012 (2)0.004 (2)0.028 (3)
C7A0.077 (4)0.031 (3)0.115 (5)0.012 (2)0.013 (3)0.013 (3)
C7B0.089 (4)0.048 (3)0.057 (3)0.031 (3)0.003 (2)0.015 (2)
C8A0.045 (3)0.046 (3)0.056 (3)0.008 (2)0.006 (2)0.005 (2)
C8B0.055 (3)0.049 (3)0.042 (3)0.014 (2)0.008 (2)0.009 (2)
C9A0.054 (3)0.081 (4)0.071 (4)0.010 (3)0.011 (2)0.013 (3)
C9B0.054 (3)0.092 (4)0.066 (3)0.018 (3)0.008 (2)0.023 (3)
C10A0.065 (3)0.074 (4)0.071 (4)0.005 (3)0.012 (3)0.025 (3)
C10B0.060 (3)0.079 (4)0.074 (4)0.006 (3)0.002 (3)0.032 (3)
C11A0.061 (3)0.055 (3)0.058 (3)0.004 (2)0.001 (2)0.018 (2)
C11B0.055 (3)0.062 (3)0.064 (3)0.007 (2)0.005 (2)0.024 (3)
C12A0.053 (3)0.038 (3)0.045 (3)0.0042 (19)0.011 (2)0.008 (2)
C12B0.054 (3)0.047 (3)0.042 (2)0.013 (2)0.011 (2)0.011 (2)
C13A0.048 (2)0.033 (2)0.053 (3)0.0031 (18)0.010 (2)0.007 (2)
C13B0.051 (2)0.036 (2)0.043 (2)0.0090 (18)0.0050 (19)0.011 (2)
C14A0.048 (2)0.036 (2)0.044 (2)0.0065 (18)0.0111 (19)0.007 (2)
C14B0.054 (3)0.037 (2)0.045 (3)0.0088 (19)0.009 (2)0.012 (2)
C15A0.047 (2)0.040 (3)0.049 (3)0.0062 (19)0.0070 (19)0.013 (2)
C15B0.062 (3)0.034 (3)0.061 (3)0.012 (2)0.004 (2)0.015 (2)
C16A0.048 (2)0.033 (2)0.053 (3)0.0101 (18)0.001 (2)0.009 (2)
C16B0.065 (3)0.039 (3)0.058 (3)0.020 (2)0.008 (2)0.016 (2)
C17A0.045 (2)0.042 (3)0.057 (3)0.0093 (19)0.008 (2)0.014 (2)
C17B0.056 (3)0.042 (3)0.054 (3)0.013 (2)0.003 (2)0.017 (2)
C18A0.056 (3)0.055 (3)0.091 (4)0.019 (2)0.015 (3)0.012 (3)
C18B0.060 (3)0.068 (3)0.085 (4)0.009 (2)0.014 (3)0.035 (3)
C19A0.062 (3)0.038 (3)0.060 (3)0.005 (2)0.001 (2)0.021 (2)
C19B0.090 (4)0.048 (3)0.086 (4)0.010 (3)0.013 (3)0.027 (3)
C20A0.130 (5)0.072 (4)0.102 (5)0.016 (4)0.061 (4)0.004 (4)
C20B0.250 (10)0.104 (6)0.087 (5)0.041 (6)0.062 (6)0.019 (5)
F1A0.294 (7)0.085 (4)0.231 (7)0.084 (4)0.055 (6)0.066 (4)
F1B0.198 (4)0.071 (2)0.109 (3)0.060 (3)0.026 (3)0.029 (2)
N1A0.055 (2)0.040 (2)0.078 (3)0.0120 (18)0.005 (2)0.009 (2)
N1B0.070 (2)0.045 (2)0.050 (2)0.0217 (18)0.0000 (18)0.0177 (18)
N1C0.069 (3)0.085 (4)0.097 (4)0.000 (2)0.019 (3)0.036 (3)
N2A0.058 (2)0.060 (3)0.076 (3)0.019 (2)0.002 (2)0.006 (2)
N2B0.061 (2)0.074 (3)0.052 (2)0.028 (2)0.0001 (19)0.012 (2)
N3A0.051 (2)0.038 (2)0.071 (3)0.0115 (17)0.0029 (18)0.0066 (19)
N3B0.059 (2)0.049 (2)0.053 (2)0.0238 (18)0.0041 (17)0.0183 (19)
N4A0.045 (2)0.039 (2)0.056 (2)0.0087 (16)0.0028 (16)0.0127 (17)
N4B0.055 (2)0.040 (2)0.056 (2)0.0132 (16)0.0014 (17)0.0193 (18)
N5A0.048 (2)0.037 (2)0.052 (2)0.0077 (15)0.0013 (17)0.0152 (17)
N5B0.054 (2)0.037 (2)0.051 (2)0.0112 (16)0.0003 (17)0.0155 (17)
N6A0.064 (2)0.043 (2)0.071 (3)0.0115 (18)0.0117 (19)0.024 (2)
N6B0.078 (3)0.051 (3)0.091 (3)0.025 (2)0.026 (2)0.038 (2)
N7A0.057 (2)0.042 (2)0.076 (3)0.0103 (17)0.0143 (19)0.024 (2)
N7B0.074 (3)0.046 (2)0.075 (3)0.0207 (19)0.019 (2)0.028 (2)
N8A0.052 (2)0.035 (2)0.061 (3)0.0099 (16)0.0058 (18)0.0112 (19)
N8B0.089 (3)0.046 (2)0.063 (3)0.016 (2)0.019 (2)0.020 (2)
O1A0.078 (2)0.046 (2)0.067 (2)0.0236 (17)0.0075 (17)0.0097 (16)
O1B0.114 (3)0.063 (3)0.145 (4)0.050 (2)0.047 (3)0.029 (3)
O1C0.108 (3)0.087 (3)0.146 (4)0.008 (3)0.033 (3)0.031 (3)
O2A0.072 (2)0.052 (2)0.072 (2)0.0157 (16)0.0205 (17)0.0093 (17)
O2B0.114 (3)0.076 (3)0.081 (3)0.030 (2)0.029 (2)0.003 (2)
Geometric parameters (Å, º) top
C1A—C2A1.313 (12)C11B—C12B1.394 (6)
C1A—C6A1.372 (9)C11B—H11B0.9300
C1A—F1A1.378 (11)C12A—C13A1.433 (5)
C1B—F1B1.356 (7)C12B—C13B1.422 (5)
C1B—C2B1.360 (8)C13A—N3A1.312 (5)
C1B—C6B1.374 (7)C13A—C14A1.466 (5)
C1C—O1C1.211 (7)C13B—N3B1.317 (5)
C1C—N1C1.297 (7)C13B—C14B1.469 (5)
C1C—H1C0.9300C14A—N4A1.324 (5)
C2A—C3A1.343 (13)C14A—N5A1.334 (5)
C2A—H2A0.9300C14B—N4B1.329 (5)
C2B—C3B1.359 (9)C14B—N5B1.341 (5)
C2B—H2B0.9300C15A—N6A1.338 (5)
C2C—N1C1.437 (8)C15A—N4A1.357 (5)
C2C—H2C10.9600C15A—C16A1.385 (5)
C2C—H2C20.9600C15B—N6B1.354 (5)
C2C—H2C30.9600C15B—N4B1.360 (5)
C3A—C4A1.443 (11)C15B—C16B1.380 (6)
C3A—H3A0.9300C16A—C17A1.397 (6)
C3B—C4B1.364 (9)C16A—N8A1.434 (5)
C3B—H3B0.9300C16B—C17B1.389 (6)
C3C—N1C1.441 (8)C16B—N8B1.450 (5)
C3C—H3C10.9600C17A—N7A1.346 (5)
C3C—H3C20.9600C17A—N5A1.351 (5)
C3C—H3C30.9600C17B—N7B1.341 (5)
C4A—C5A1.399 (10)C17B—N5B1.350 (5)
C4A—H4A0.9300C18A—N8A1.455 (5)
C4B—C5B1.373 (7)C18A—H18A0.9600
C4B—H4B0.9300C18A—H18B0.9600
C5A—C6A1.388 (9)C18A—H18C0.9600
C5A—H5A0.9300C18B—N8B1.466 (6)
C5B—C6B1.364 (7)C18B—H18D0.9600
C5B—H5B0.9300C18B—H18E0.9600
C6A—C7A1.473 (9)C18B—H18F0.9600
C6B—C7B1.509 (6)C19A—O1A1.228 (5)
C7A—N1A1.444 (6)C19A—O2A1.342 (5)
C7A—H7A10.9700C19A—N8A1.347 (6)
C7A—H7A20.9700C19B—O1B1.225 (6)
C7B—N1B1.449 (5)C19B—N8B1.285 (7)
C7B—H7B10.9700C19B—O2B1.349 (7)
C7B—H7B20.9700C20A—O2A1.440 (6)
C8A—N2A1.343 (5)C20A—H20A0.9600
C8A—N1A1.351 (5)C20A—H20B0.9600
C8A—C12A1.399 (6)C20A—H20C0.9600
C8B—N2B1.340 (5)C20B—O2B1.427 (7)
C8B—N1B1.360 (5)C20B—H20D0.9600
C8B—C12B1.403 (5)C20B—H20E0.9600
C9A—N2A1.327 (6)C20B—H20F0.9600
C9A—C10A1.388 (7)N1A—N3A1.360 (4)
C9A—H9A0.9300N1B—N3B1.356 (4)
C9B—N2B1.335 (6)N6A—H6A10.8600
C9B—C10B1.387 (7)N6A—H6A20.8600
C9B—H9B0.9300N6B—H6B10.8600
C10A—C11A1.366 (6)N6B—H6B20.8600
C10A—H10A0.9300N7A—H7A30.8600
C10B—C11B1.369 (6)N7A—H7A40.8600
C10B—H10B0.9300N7B—H7B30.8600
C11A—C12A1.384 (6)N7B—H7B40.8600
C11A—H11A0.9300
C2A—C1A—C6A126.1 (11)C12A—C13A—C14A127.8 (4)
C2A—C1A—F1A118.3 (9)N3B—C13B—C12B110.7 (3)
C6A—C1A—F1A115.6 (9)N3B—C13B—C14B119.8 (3)
F1B—C1B—C2B118.9 (6)C12B—C13B—C14B129.5 (4)
F1B—C1B—C6B117.6 (5)N4A—C14A—N5A128.2 (3)
C2B—C1B—C6B123.5 (6)N4A—C14A—C13A114.6 (3)
O1C—C1C—N1C125.5 (7)N5A—C14A—C13A117.2 (4)
O1C—C1C—H1C117.2N4B—C14B—N5B127.9 (3)
N1C—C1C—H1C117.2N4B—C14B—C13B116.7 (3)
C1A—C2A—C3A118.7 (10)N5B—C14B—C13B115.4 (4)
C1A—C2A—H2A120.7N6A—C15A—N4A115.7 (3)
C3A—C2A—H2A120.7N6A—C15A—C16A123.5 (4)
C3B—C2B—C1B119.0 (6)N4A—C15A—C16A120.8 (4)
C3B—C2B—H2B120.5N6B—C15B—N4B116.7 (4)
C1B—C2B—H2B120.5N6B—C15B—C16B121.7 (4)
N1C—C2C—H2C1109.5N4B—C15B—C16B121.6 (4)
N1C—C2C—H2C2109.5C15A—C16A—C17A118.1 (4)
H2C1—C2C—H2C2109.5C15A—C16A—N8A122.5 (4)
N1C—C2C—H2C3109.5C17A—C16A—N8A119.3 (3)
H2C1—C2C—H2C3109.5C15B—C16B—C17B117.9 (4)
H2C2—C2C—H2C3109.5C15B—C16B—N8B122.5 (4)
C2A—C3A—C4A120.3 (8)C17B—C16B—N8B119.5 (4)
C2A—C3A—H3A119.9N7A—C17A—N5A116.4 (4)
C4A—C3A—H3A119.9N7A—C17A—C16A122.3 (4)
C2B—C3B—C4B119.4 (6)N5A—C17A—C16A121.3 (4)
C2B—C3B—H3B120.3N7B—C17B—N5B116.4 (4)
C4B—C3B—H3B120.3N7B—C17B—C16B121.9 (4)
N1C—C3C—H3C1109.5N5B—C17B—C16B121.7 (4)
N1C—C3C—H3C2109.5N8A—C18A—H18A109.5
H3C1—C3C—H3C2109.5N8A—C18A—H18B109.5
N1C—C3C—H3C3109.5H18A—C18A—H18B109.5
H3C1—C3C—H3C3109.5N8A—C18A—H18C109.5
H3C2—C3C—H3C3109.5H18A—C18A—H18C109.5
C5A—C4A—C3A118.3 (9)H18B—C18A—H18C109.5
C5A—C4A—H4A120.9N8B—C18B—H18D109.5
C3A—C4A—H4A120.9N8B—C18B—H18E109.5
C3B—C4B—C5B120.4 (6)H18D—C18B—H18E109.5
C3B—C4B—H4B119.8N8B—C18B—H18F109.5
C5B—C4B—H4B119.8H18D—C18B—H18F109.5
C6A—C5A—C4A119.5 (9)H18E—C18B—H18F109.5
C6A—C5A—H5A120.3O1A—C19A—O2A123.5 (5)
C4A—C5A—H5A120.3O1A—C19A—N8A124.3 (4)
C6B—C5B—C4B121.5 (5)O2A—C19A—N8A112.1 (4)
C6B—C5B—H5B119.2O1B—C19B—N8B123.0 (7)
C4B—C5B—H5B119.2O1B—C19B—O2B124.9 (6)
C1A—C6A—C5A117.2 (9)N8B—C19B—O2B112.2 (5)
C1A—C6A—C7A118.9 (8)O2A—C20A—H20A109.5
C5A—C6A—C7A123.9 (6)O2A—C20A—H20B109.5
C5B—C6B—C1B116.1 (5)H20A—C20A—H20B109.5
C5B—C6B—C7B125.6 (4)O2A—C20A—H20C109.5
C1B—C6B—C7B118.3 (5)H20A—C20A—H20C109.5
N1A—C7A—C6A113.9 (5)H20B—C20A—H20C109.5
N1A—C7A—H7A1108.8O2B—C20B—H20D109.5
C6A—C7A—H7A1108.8O2B—C20B—H20E109.5
N1A—C7A—H7A2108.8H20D—C20B—H20E109.5
C6A—C7A—H7A2108.8O2B—C20B—H20F109.5
H7A1—C7A—H7A2107.7H20D—C20B—H20F109.5
N1B—C7B—C6B114.2 (4)H20E—C20B—H20F109.5
N1B—C7B—H7B1108.7C8A—N1A—N3A111.3 (3)
C6B—C7B—H7B1108.7C8A—N1A—C7A128.2 (4)
N1B—C7B—H7B2108.7N3A—N1A—C7A120.3 (4)
C6B—C7B—H7B2108.7N3B—N1B—C8B111.5 (3)
H7B1—C7B—H7B2107.6N3B—N1B—C7B120.4 (4)
N2A—C8A—N1A125.3 (4)C8B—N1B—C7B128.1 (4)
N2A—C8A—C12A127.6 (4)C1C—N1C—C2C123.4 (6)
N1A—C8A—C12A107.1 (4)C1C—N1C—C3C118.7 (6)
N2B—C8B—N1B125.3 (4)C2C—N1C—C3C117.9 (6)
N2B—C8B—C12B128.3 (4)C9A—N2A—C8A112.2 (4)
N1B—C8B—C12B106.4 (3)C9B—N2B—C8B112.3 (4)
N2A—C9A—C10A125.3 (4)C13A—N3A—N1A107.0 (3)
N2A—C9A—H9A117.4C13B—N3B—N1B106.8 (3)
C10A—C9A—H9A117.4C14A—N4A—C15A116.1 (3)
N2B—C9B—C10B125.2 (4)C14B—N4B—C15B115.6 (3)
N2B—C9B—H9B117.4C14A—N5A—C17A115.4 (3)
C10B—C9B—H9B117.4C14B—N5B—C17B115.4 (3)
C11A—C10A—C9A120.8 (5)C15A—N6A—H6A1120.0
C11A—C10A—H10A119.6C15A—N6A—H6A2120.0
C9A—C10A—H10A119.6H6A1—N6A—H6A2120.0
C11B—C10B—C9B120.6 (5)C15B—N6B—H6B1120.0
C11B—C10B—H10B119.7C15B—N6B—H6B2120.0
C9B—C10B—H10B119.7H6B1—N6B—H6B2120.0
C10A—C11A—C12A116.8 (4)C17A—N7A—H7A3120.0
C10A—C11A—H11A121.6C17A—N7A—H7A4120.0
C12A—C11A—H11A121.6H7A3—N7A—H7A4120.0
C10B—C11B—C12B117.4 (4)C17B—N7B—H7B3120.0
C10B—C11B—H11B121.3C17B—N7B—H7B4120.0
C12B—C11B—H11B121.3H7B3—N7B—H7B4120.0
C11A—C12A—C8A117.2 (4)C19A—N8A—C16A122.5 (4)
C11A—C12A—C13A138.7 (4)C19A—N8A—C18A118.6 (4)
C8A—C12A—C13A104.1 (4)C16A—N8A—C18A118.9 (4)
C11B—C12B—C8B116.2 (4)C19B—N8B—C16B121.9 (5)
C11B—C12B—C13B139.2 (4)C19B—N8B—C18B121.0 (5)
C8B—C12B—C13B104.6 (4)C16B—N8B—C18B116.8 (4)
N3A—C13A—C12A110.5 (3)C19A—O2A—C20A115.6 (4)
N3A—C13A—C14A121.7 (4)C19B—O2B—C20B118.3 (5)
C6A—C1A—C2A—C3A0.4 (14)N8A—C16A—C17A—N5A179.7 (4)
F1A—C1A—C2A—C3A177.5 (8)C15B—C16B—C17B—N7B179.4 (5)
F1B—C1B—C2B—C3B179.9 (6)N8B—C16B—C17B—N7B3.5 (7)
C6B—C1B—C2B—C3B0.3 (10)C15B—C16B—C17B—N5B0.5 (7)
C1A—C2A—C3A—C4A0.7 (14)N8B—C16B—C17B—N5B177.6 (4)
C1B—C2B—C3B—C4B0.5 (10)N2A—C8A—N1A—N3A176.5 (4)
C2A—C3A—C4A—C5A1.4 (13)C12A—C8A—N1A—N3A2.2 (5)
C2B—C3B—C4B—C5B0.9 (10)N2A—C8A—N1A—C7A2.2 (8)
C3A—C4A—C5A—C6A1.0 (11)C12A—C8A—N1A—C7A176.5 (5)
C3B—C4B—C5B—C6B0.6 (8)C6A—C7A—N1A—C8A88.4 (6)
C2A—C1A—C6A—C5A0.7 (11)C6A—C7A—N1A—N3A85.5 (6)
F1A—C1A—C6A—C5A177.2 (6)N2B—C8B—N1B—N3B177.3 (4)
C2A—C1A—C6A—C7A179.6 (7)C12B—C8B—N1B—N3B0.6 (5)
F1A—C1A—C6A—C7A2.5 (9)N2B—C8B—N1B—C7B0.6 (8)
C4A—C5A—C6A—C1A0.1 (10)C12B—C8B—N1B—C7B178.5 (4)
C4A—C5A—C6A—C7A179.6 (6)C6B—C7B—N1B—N3B72.4 (5)
C4B—C5B—C6B—C1B0.1 (7)C6B—C7B—N1B—C8B109.9 (5)
C4B—C5B—C6B—C7B179.0 (5)O1C—C1C—N1C—C2C178.4 (6)
F1B—C1B—C6B—C5B179.8 (5)O1C—C1C—N1C—C3C3.6 (9)
C2B—C1B—C6B—C5B0.6 (8)C10A—C9A—N2A—C8A1.1 (8)
F1B—C1B—C6B—C7B0.8 (7)N1A—C8A—N2A—C9A179.3 (5)
C2B—C1B—C6B—C7B179.5 (5)C12A—C8A—N2A—C9A0.8 (7)
C1A—C6A—C7A—N1A166.2 (5)C10B—C9B—N2B—C8B0.3 (8)
C5A—C6A—C7A—N1A14.1 (8)N1B—C8B—N2B—C9B178.2 (4)
C5B—C6B—C7B—N1B16.5 (7)C12B—C8B—N2B—C9B0.7 (7)
C1B—C6B—C7B—N1B164.7 (4)C12A—C13A—N3A—N1A0.5 (5)
N2A—C9A—C10A—C11A1.7 (9)C14A—C13A—N3A—N1A177.7 (4)
N2B—C9B—C10B—C11B0.0 (9)C8A—N1A—N3A—C13A1.7 (5)
C9A—C10A—C11A—C12A0.3 (8)C7A—N1A—N3A—C13A176.5 (5)
C9B—C10B—C11B—C12B0.1 (8)C12B—C13B—N3B—N1B0.7 (5)
C10A—C11A—C12A—C8A1.3 (7)C14B—C13B—N3B—N1B178.4 (4)
C10A—C11A—C12A—C13A177.2 (5)C8B—N1B—N3B—C13B0.8 (5)
N2A—C8A—C12A—C11A2.1 (7)C7B—N1B—N3B—C13B178.9 (4)
N1A—C8A—C12A—C11A179.2 (4)N5A—C14A—N4A—C15A2.2 (6)
N2A—C8A—C12A—C13A177.0 (5)C13A—C14A—N4A—C15A177.4 (4)
N1A—C8A—C12A—C13A1.7 (5)N6A—C15A—N4A—C14A179.5 (4)
C10B—C11B—C12B—C8B0.4 (7)C16A—C15A—N4A—C14A1.0 (6)
C10B—C11B—C12B—C13B177.3 (5)N5B—C14B—N4B—C15B2.5 (7)
N2B—C8B—C12B—C11B0.8 (7)C13B—C14B—N4B—C15B178.0 (4)
N1B—C8B—C12B—C11B178.6 (4)N6B—C15B—N4B—C14B179.8 (4)
N2B—C8B—C12B—C13B177.7 (4)C16B—C15B—N4B—C14B1.4 (7)
N1B—C8B—C12B—C13B0.2 (5)N4A—C14A—N5A—C17A2.7 (6)
C11A—C12A—C13A—N3A179.4 (5)C13A—C14A—N5A—C17A176.9 (4)
C8A—C12A—C13A—N3A0.7 (5)N7A—C17A—N5A—C14A179.1 (4)
C11A—C12A—C13A—C14A2.4 (9)C16A—C17A—N5A—C14A0.1 (6)
C8A—C12A—C13A—C14A176.3 (4)N4B—C14B—N5B—C17B2.0 (7)
C11B—C12B—C13B—N3B177.6 (5)C13B—C14B—N5B—C17B178.5 (4)
C8B—C12B—C13B—N3B0.3 (5)N7B—C17B—N5B—C14B178.6 (4)
C11B—C12B—C13B—C14B3.5 (9)C16B—C17B—N5B—C14B0.4 (6)
C8B—C12B—C13B—C14B178.7 (4)O1A—C19A—N8A—C16A174.9 (4)
N3A—C13A—C14A—N4A179.6 (4)O2A—C19A—N8A—C16A5.0 (6)
C12A—C13A—C14A—N4A3.7 (6)O1A—C19A—N8A—C18A3.1 (6)
N3A—C13A—C14A—N5A0.8 (6)O2A—C19A—N8A—C18A177.0 (4)
C12A—C13A—C14A—N5A175.9 (4)C15A—C16A—N8A—C19A83.9 (6)
N3B—C13B—C14B—N4B179.3 (4)C17A—C16A—N8A—C19A99.3 (5)
C12B—C13B—C14B—N4B1.8 (7)C15A—C16A—N8A—C18A98.1 (5)
N3B—C13B—C14B—N5B0.3 (6)C17A—C16A—N8A—C18A78.6 (5)
C12B—C13B—C14B—N5B178.6 (4)O1B—C19B—N8B—C16B176.0 (5)
N6A—C15A—C16A—C17A177.2 (4)O2B—C19B—N8B—C16B4.5 (7)
N4A—C15A—C16A—C17A3.4 (6)O1B—C19B—N8B—C18B2.4 (8)
N6A—C15A—C16A—N8A0.5 (7)O2B—C19B—N8B—C18B178.2 (4)
N4A—C15A—C16A—N8A179.9 (4)C15B—C16B—N8B—C19B95.0 (6)
N6B—C15B—C16B—C17B178.8 (5)C17B—C16B—N8B—C19B88.0 (6)
N4B—C15B—C16B—C17B0.1 (7)C15B—C16B—N8B—C18B91.1 (6)
N6B—C15B—C16B—N8B1.7 (8)C17B—C16B—N8B—C18B85.9 (5)
N4B—C15B—C16B—N8B177.0 (5)O1A—C19A—O2A—C20A0.9 (6)
C15A—C16A—C17A—N7A176.3 (4)N8A—C19A—O2A—C20A179.0 (4)
N8A—C16A—C17A—N7A0.6 (7)O1B—C19B—O2B—C20B4.6 (9)
C15A—C16A—C17A—N5A2.9 (7)N8B—C19B—O2B—C20B175.9 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6B—H6B2···O1Ai0.862.253.065 (5)159
N6B—H6B1···O1Aii0.862.363.151 (5)152
N6A—H6A2···O1Biii0.862.142.964 (5)160
N6A—H6A1···O1Civ0.862.193.046 (6)173
N7A—H7A3···N5B0.862.263.098 (5)166
N7A—H7A3···N3B0.862.562.982 (5)111
N7B—H7B3···N5A0.862.163.017 (5)175
Symmetry codes: (i) x, y+1, z; (ii) x, y+1, z+2; (iii) x, y1, z; (iv) x+1, y+1, z+1.
(V) top
Crystal data top
C20H19FN8O2Z = 4
Mr = 422.43F(000) = 880
Triclinic, P1Dx = 1.235 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.1749 (8) ÅCell parameters from 9709 reflections
b = 13.7062 (9) Åθ = 3.0–27.5°
c = 14.4719 (10) ŵ = 0.09 mm1
α = 70.217 (2)°T = 296 K
β = 72.912 (1)°Needle, colorless
γ = 70.776 (3)°0.52 × 0.26 × 0.12 mm
V = 2272.5 (3) Å3
Data collection top
Rigaku RAXIS-RAPID/ZJUG
diffractometer
10187 independent reflections
Radiation source: rotating anode3669 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
Detector resolution: 10.00 pixels mm-1θmax = 27.5°, θmin = 3.1°
ω scansh = 1617
Absorption correction: multi-scan
Higashi, T. (1995)
k = 1617
Tmin = 0.954, Tmax = 0.989l = 018
10187 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)] = 0.099H-atom parameters constrained
wR(F2) = 0.315 w = 1/[σ2(Fo2) + (0.1238P)2 + 1.5P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.035
10187 reflectionsΔρmax = 0.43 e Å3
564 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (3)
Special details top

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

Refinement. 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 > 2sigma(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
C1A0.0199 (5)0.6299 (4)0.7257 (6)0.0826 (18)
C1B0.0089 (4)1.1058 (4)0.2031 (5)0.0670 (15)
C2A0.0472 (6)0.6300 (5)0.8200 (7)0.115 (3)
H2A0.12260.64100.82910.138*
C2B0.0660 (5)1.1086 (4)0.2911 (5)0.0825 (18)
H2B0.14001.11770.29450.099*
C3A0.0034 (8)0.6143 (6)0.8966 (7)0.116 (3)
H3A0.04730.61410.96010.140*
C3B0.0294 (6)1.0978 (4)0.3736 (6)0.089 (2)
H3B0.07841.09860.43470.107*
C4A0.1059 (7)0.5988 (5)0.8814 (6)0.106 (2)
H4A0.13650.58590.93610.128*
C4B0.0780 (6)1.0859 (4)0.3665 (5)0.0829 (17)
H4B0.10201.07910.42330.100*
C5A0.1755 (5)0.6011 (4)0.7877 (5)0.0829 (18)
H5A0.25040.59180.77960.100*
C5B0.1532 (5)1.0835 (4)0.2780 (4)0.0668 (14)
H5B0.22701.07510.27510.080*
C6A0.1306 (4)0.6173 (4)0.7073 (4)0.0644 (14)
C6B0.1184 (4)1.0936 (3)0.1934 (4)0.0556 (13)
C7A0.1965 (4)0.6200 (4)0.6034 (4)0.0672 (14)
H7A10.19710.55680.58690.081*
H7A20.15980.68220.55710.081*
C7B0.1939 (4)1.0932 (4)0.0916 (4)0.0648 (14)
H7B10.19851.02860.07510.078*
H7B20.16181.15410.04140.078*
C8A0.3538 (4)0.7086 (4)0.5383 (4)0.0528 (12)
C8B0.3491 (4)1.1827 (4)0.0384 (4)0.0539 (12)
C9A0.3658 (5)0.8723 (5)0.4501 (5)0.0813 (17)
H9A0.33390.94250.41780.098*
C9B0.3637 (5)1.3437 (4)0.0535 (4)0.0782 (17)
H9B0.33401.41300.08910.094*
C10A0.4763 (5)0.8455 (4)0.4469 (5)0.0814 (17)
H10A0.51560.89710.41340.098*
C10B0.4738 (5)1.3166 (4)0.0496 (4)0.0785 (17)
H10B0.51441.36730.08230.094*
C11A0.5300 (4)0.7432 (4)0.4925 (4)0.0651 (14)
H11A0.60490.72400.49160.078*
C11B0.5232 (4)1.2165 (4)0.0017 (4)0.0690 (15)
H11B0.59701.19720.00480.083*
C12A0.4659 (4)0.6703 (4)0.5401 (4)0.0537 (12)
C12B0.4580 (4)1.1455 (3)0.0488 (3)0.0499 (11)
C13A0.4807 (4)0.5603 (3)0.5930 (4)0.0538 (12)
C13B0.4710 (4)1.0351 (4)0.1054 (4)0.0528 (12)
C14A0.5808 (4)0.4780 (3)0.6212 (4)0.0515 (12)
C14B0.5676 (4)0.9579 (3)0.1424 (3)0.0480 (11)
C15A0.7617 (4)0.4385 (3)0.6201 (4)0.0549 (12)
C15B0.7445 (4)0.9236 (4)0.1556 (4)0.0566 (12)
C16A0.7582 (4)0.3361 (4)0.6753 (4)0.0577 (13)
C16B0.7406 (3)0.8194 (3)0.2111 (4)0.0514 (12)
C17A0.6598 (4)0.3078 (4)0.7020 (4)0.0535 (12)
C17B0.6458 (4)0.7884 (4)0.2266 (4)0.0515 (12)
C18A0.9211 (4)0.1895 (4)0.6388 (5)0.0826 (18)
H18A0.98260.14050.66680.124*
H18B0.94710.23450.57480.124*
H18C0.87800.14980.63040.124*
C18B0.9060 (4)0.6678 (4)0.1942 (5)0.0795 (17)
H18D0.96680.62530.22600.119*
H18E0.93280.70690.12730.119*
H18F0.86630.62160.19140.119*
C19A0.8717 (5)0.2299 (4)0.7995 (5)0.0747 (17)
C19B0.8448 (4)0.7326 (4)0.3449 (4)0.0583 (13)
C20A0.8079 (6)0.2710 (6)0.9542 (5)0.121 (3)
H20A0.81210.19630.98560.181*
H20B0.74490.31330.98960.181*
H20C0.87310.28660.95590.181*
C20B0.7813 (6)0.8055 (6)0.4813 (5)0.106 (2)
H20D0.74520.75350.53040.159*
H20E0.74650.87460.49380.159*
H20F0.85710.78540.48550.159*
F1A0.0244 (3)0.6453 (3)0.6465 (4)0.1206 (14)
F1B0.0266 (3)1.1173 (3)0.1196 (3)0.0931 (11)
N1A0.3080 (3)0.6240 (3)0.5875 (3)0.0606 (11)
N1B0.3027 (3)1.0976 (3)0.0864 (3)0.0591 (11)
N2A0.3000 (4)0.8062 (3)0.4956 (3)0.0691 (12)
N2B0.2973 (4)1.2790 (3)0.0106 (3)0.0674 (12)
N3A0.3858 (3)0.5330 (3)0.6210 (3)0.0616 (11)
N3B0.3774 (3)1.0088 (3)0.1278 (3)0.0583 (11)
N4A0.6716 (3)0.5131 (3)0.5897 (3)0.0577 (11)
N4B0.6562 (3)0.9936 (3)0.1195 (3)0.0557 (10)
N5A0.5679 (3)0.3815 (3)0.6745 (3)0.0541 (10)
N5B0.5570 (3)0.8593 (3)0.1912 (3)0.0521 (10)
N6A0.8555 (3)0.4714 (3)0.5887 (4)0.0811 (15)
H6A10.85520.53570.55210.097*
H6A20.91540.42800.60540.097*
N6B0.8339 (3)0.9586 (3)0.1352 (4)0.0795 (15)
H6B10.83381.02340.10040.095*
H6B20.89170.91640.15690.095*
N7A0.6501 (3)0.2088 (3)0.7541 (3)0.0678 (12)
H7A30.58760.19420.76880.081*
H7A40.70620.15990.77290.081*
N7B0.6367 (3)0.6882 (3)0.2768 (3)0.0651 (12)
H7B30.57650.67160.28520.078*
H7B40.69100.64080.30050.078*
N8A0.8537 (3)0.2558 (3)0.7062 (4)0.0633 (12)
N8B0.8326 (3)0.7434 (3)0.2519 (3)0.0600 (11)
O1A0.9433 (4)0.1554 (3)0.8321 (4)0.1082 (16)
O1B0.9136 (3)0.6604 (3)0.3857 (3)0.0827 (12)
O2A0.7984 (3)0.2961 (3)0.8526 (3)0.0844 (12)
O2B0.7738 (3)0.8101 (3)0.3826 (3)0.0720 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.049 (4)0.069 (3)0.106 (5)0.007 (3)0.009 (4)0.007 (3)
C1B0.049 (3)0.054 (3)0.089 (4)0.010 (2)0.023 (3)0.003 (3)
C2A0.057 (4)0.079 (4)0.145 (8)0.009 (3)0.033 (5)0.007 (5)
C2B0.041 (3)0.078 (4)0.096 (5)0.011 (3)0.004 (4)0.002 (3)
C3A0.112 (8)0.085 (5)0.091 (6)0.007 (5)0.008 (5)0.004 (4)
C3B0.076 (5)0.068 (4)0.089 (5)0.006 (3)0.016 (4)0.018 (3)
C4A0.118 (7)0.076 (4)0.089 (6)0.001 (4)0.019 (5)0.003 (4)
C4B0.080 (5)0.080 (4)0.083 (5)0.015 (3)0.015 (4)0.022 (3)
C5A0.069 (4)0.079 (4)0.072 (4)0.003 (3)0.008 (4)0.010 (3)
C5B0.053 (3)0.072 (3)0.065 (4)0.010 (3)0.014 (3)0.010 (3)
C6A0.041 (3)0.053 (3)0.075 (4)0.007 (2)0.005 (3)0.000 (3)
C6B0.032 (3)0.051 (3)0.069 (3)0.007 (2)0.007 (2)0.004 (2)
C7A0.031 (3)0.082 (3)0.079 (4)0.011 (2)0.014 (3)0.011 (3)
C7B0.042 (3)0.074 (3)0.072 (4)0.014 (2)0.021 (3)0.005 (3)
C8A0.032 (3)0.058 (3)0.055 (3)0.002 (2)0.009 (2)0.008 (2)
C8B0.040 (3)0.061 (3)0.055 (3)0.006 (2)0.011 (2)0.014 (2)
C9A0.069 (4)0.068 (3)0.084 (4)0.008 (3)0.022 (3)0.004 (3)
C9B0.078 (4)0.061 (3)0.078 (4)0.003 (3)0.024 (3)0.004 (3)
C10A0.070 (4)0.067 (3)0.092 (5)0.020 (3)0.016 (3)0.000 (3)
C10B0.066 (4)0.062 (3)0.090 (4)0.022 (3)0.016 (3)0.007 (3)
C11A0.050 (3)0.065 (3)0.068 (4)0.016 (3)0.010 (3)0.004 (3)
C11B0.056 (3)0.066 (3)0.079 (4)0.015 (3)0.016 (3)0.012 (3)
C12A0.042 (3)0.056 (3)0.056 (3)0.000 (2)0.014 (2)0.015 (2)
C12B0.040 (3)0.060 (3)0.045 (3)0.012 (2)0.008 (2)0.009 (2)
C13A0.029 (3)0.055 (3)0.069 (3)0.003 (2)0.011 (2)0.013 (2)
C13B0.033 (3)0.055 (3)0.065 (3)0.011 (2)0.011 (2)0.009 (2)
C14A0.034 (3)0.051 (3)0.065 (3)0.006 (2)0.015 (2)0.010 (2)
C14B0.036 (3)0.052 (3)0.050 (3)0.008 (2)0.013 (2)0.006 (2)
C15A0.037 (3)0.048 (3)0.076 (4)0.012 (2)0.015 (2)0.009 (2)
C15B0.036 (3)0.056 (3)0.076 (4)0.011 (2)0.020 (2)0.010 (3)
C16A0.031 (3)0.058 (3)0.079 (4)0.009 (2)0.014 (2)0.012 (3)
C16B0.029 (2)0.051 (3)0.070 (3)0.006 (2)0.017 (2)0.011 (2)
C17A0.038 (3)0.056 (3)0.060 (3)0.008 (2)0.011 (2)0.010 (2)
C17B0.032 (3)0.060 (3)0.058 (3)0.008 (2)0.011 (2)0.012 (2)
C18A0.048 (3)0.060 (3)0.132 (6)0.001 (3)0.018 (3)0.030 (3)
C18B0.044 (3)0.069 (3)0.127 (5)0.001 (3)0.020 (3)0.038 (3)
C19A0.060 (4)0.060 (3)0.105 (5)0.026 (3)0.042 (4)0.008 (3)
C19B0.040 (3)0.063 (3)0.067 (4)0.021 (2)0.020 (3)0.005 (3)
C20A0.125 (7)0.162 (7)0.079 (5)0.059 (6)0.045 (5)0.007 (5)
C20B0.085 (5)0.149 (6)0.095 (5)0.031 (5)0.019 (4)0.045 (5)
F1A0.052 (2)0.142 (3)0.166 (4)0.024 (2)0.024 (3)0.038 (3)
F1B0.055 (2)0.110 (3)0.112 (3)0.0257 (18)0.036 (2)0.006 (2)
N1A0.030 (2)0.059 (2)0.075 (3)0.0009 (18)0.013 (2)0.005 (2)
N1B0.036 (2)0.064 (2)0.071 (3)0.0071 (19)0.021 (2)0.007 (2)
N2A0.054 (3)0.063 (3)0.072 (3)0.002 (2)0.015 (2)0.005 (2)
N2B0.053 (3)0.062 (3)0.069 (3)0.001 (2)0.015 (2)0.007 (2)
N3A0.040 (2)0.061 (2)0.074 (3)0.0067 (19)0.014 (2)0.012 (2)
N3B0.038 (2)0.057 (2)0.071 (3)0.0061 (19)0.020 (2)0.005 (2)
N4A0.037 (2)0.053 (2)0.076 (3)0.0072 (18)0.018 (2)0.007 (2)
N4B0.039 (2)0.050 (2)0.074 (3)0.0112 (18)0.016 (2)0.0075 (19)
N5A0.031 (2)0.056 (2)0.067 (3)0.0077 (17)0.0120 (19)0.008 (2)
N5B0.038 (2)0.056 (2)0.061 (3)0.0123 (18)0.0162 (19)0.0078 (19)
N6A0.042 (3)0.057 (2)0.131 (4)0.013 (2)0.033 (3)0.005 (3)
N6B0.046 (3)0.060 (2)0.129 (4)0.023 (2)0.036 (3)0.005 (3)
N7A0.038 (2)0.056 (2)0.099 (3)0.0123 (19)0.020 (2)0.003 (2)
N7B0.045 (2)0.056 (2)0.090 (3)0.0172 (19)0.026 (2)0.000 (2)
N8A0.038 (2)0.050 (2)0.091 (3)0.0068 (18)0.018 (2)0.006 (2)
N8B0.036 (2)0.052 (2)0.085 (3)0.0070 (18)0.017 (2)0.011 (2)
O1A0.078 (3)0.079 (3)0.161 (5)0.005 (2)0.075 (3)0.005 (3)
O1B0.055 (2)0.080 (2)0.098 (3)0.0128 (19)0.036 (2)0.007 (2)
O2A0.072 (3)0.095 (3)0.086 (3)0.011 (2)0.037 (2)0.015 (2)
O2B0.054 (2)0.088 (3)0.072 (3)0.009 (2)0.0181 (19)0.025 (2)
Geometric parameters (Å, º) top
C1A—F1A1.359 (7)C13A—C14A1.484 (6)
C1A—C6A1.367 (7)C13B—N3B1.317 (6)
C1A—C2A1.391 (9)C13B—C14B1.469 (6)
C1B—F1B1.364 (6)C14A—N5A1.323 (6)
C1B—C2B1.366 (8)C14A—N4A1.335 (6)
C1B—C6B1.367 (7)C14B—N4B1.322 (5)
C2A—C3A1.320 (11)C14B—N5B1.328 (5)
C2A—H2A0.9300C15A—N6A1.355 (6)
C2B—C3B1.361 (9)C15A—N4A1.360 (5)
C2B—H2B0.9300C15A—C16A1.369 (6)
C3A—C4A1.345 (10)C15B—N6B1.333 (6)
C3A—H3A0.9300C15B—N4B1.353 (5)
C3B—C4B1.347 (8)C15B—C16B1.391 (6)
C3B—H3B0.9300C16A—C17A1.383 (6)
C4A—C5A1.393 (9)C16A—N8A1.443 (6)
C4A—H4A0.9300C16B—C17B1.382 (6)
C4B—C5B1.373 (8)C16B—N8B1.441 (5)
C4B—H4B0.9300C17A—N7A1.338 (6)
C5A—C6A1.376 (8)C17A—N5A1.361 (5)
C5A—H5A0.9300C17B—N7B1.346 (6)
C5B—C6B1.379 (7)C17B—N5B1.357 (5)
C5B—H5B0.9300C18A—N8A1.458 (6)
C6A—C7A1.494 (7)C18A—H18A0.9600
C6B—C7B1.517 (7)C18A—H18B0.9600
C7A—N1A1.435 (6)C18A—H18C0.9600
C7A—H7A10.9700C18B—N8B1.470 (6)
C7A—H7A20.9700C18B—H18D0.9600
C7B—N1B1.434 (6)C18B—H18E0.9600
C7B—H7B10.9700C18B—H18F0.9600
C7B—H7B20.9700C19A—O1A1.207 (6)
C8A—N2A1.322 (5)C19A—N8A1.346 (7)
C8A—N1A1.365 (6)C19A—O2A1.344 (7)
C8A—C12A1.400 (6)C19B—O1B1.215 (5)
C8B—N2B1.331 (6)C19B—O2B1.318 (6)
C8B—N1B1.374 (6)C19B—N8B1.355 (6)
C8B—C12B1.390 (6)C20A—O2A1.426 (7)
C9A—N2A1.336 (7)C20A—H20A0.9600
C9A—C10A1.369 (8)C20A—H20B0.9600
C9A—H9A0.9300C20A—H20C0.9600
C9B—N2B1.325 (7)C20B—O2B1.439 (7)
C9B—C10B1.387 (8)C20B—H20D0.9600
C9B—H9B0.9300C20B—H20E0.9600
C10A—C11A1.378 (7)C20B—H20F0.9600
C10A—H10A0.9300N1A—N3A1.373 (5)
C10B—C11B1.365 (7)N1B—N3B1.369 (5)
C10B—H10B0.9300N6A—H6A10.8600
C11A—C12A1.391 (7)N6A—H6A20.8600
C11A—H11A0.9300N6B—H6B10.8600
C11B—C12B1.382 (6)N6B—H6B20.8600
C11B—H11B0.9300N7A—H7A30.8600
C12A—C13A1.418 (6)N7A—H7A40.8600
C12B—C13B1.436 (6)N7B—H7B30.8600
C13A—N3A1.332 (6)N7B—H7B40.8600
F1A—C1A—C6A117.1 (6)N4A—C14A—C13A114.5 (4)
F1A—C1A—C2A120.2 (7)N4B—C14B—N5B127.8 (4)
C6A—C1A—C2A122.7 (7)N4B—C14B—C13B116.1 (4)
F1B—C1B—C2B119.0 (5)N5B—C14B—C13B116.0 (4)
F1B—C1B—C6B117.5 (5)N6A—C15A—N4A115.5 (4)
C2B—C1B—C6B123.5 (6)N6A—C15A—C16A122.5 (4)
C3A—C2A—C1A119.7 (8)N4A—C15A—C16A122.0 (4)
C3A—C2A—H2A120.1N6B—C15B—N4B117.3 (4)
C1A—C2A—H2A120.1N6B—C15B—C16B122.3 (4)
C3B—C2B—C1B118.2 (6)N4B—C15B—C16B120.4 (4)
C3B—C2B—H2B120.9C15A—C16A—C17A119.1 (4)
C1B—C2B—H2B120.9C15A—C16A—N8A122.4 (4)
C2A—C3A—C4A118.9 (8)C17A—C16A—N8A118.5 (4)
C2A—C3A—H3A120.5C17B—C16B—C15B118.7 (4)
C4A—C3A—H3A120.5C17B—C16B—N8B119.6 (4)
C4B—C3B—C2B119.8 (6)C15B—C16B—N8B121.8 (4)
C4B—C3B—H3B120.1N7A—C17A—N5A117.1 (4)
C2B—C3B—H3B120.1N7A—C17A—C16A122.8 (4)
C3A—C4A—C5A123.2 (8)N5A—C17A—C16A120.1 (4)
C3A—C4A—H4A118.4N7B—C17B—N5B117.0 (4)
C5A—C4A—H4A118.4N7B—C17B—C16B122.3 (4)
C3B—C4B—C5B122.0 (6)N5B—C17B—C16B120.7 (4)
C3B—C4B—H4B119.0N8A—C18A—H18A109.5
C5B—C4B—H4B119.0N8A—C18A—H18B109.5
C6A—C5A—C4A118.4 (6)H18A—C18A—H18B109.5
C6A—C5A—H5A120.8N8A—C18A—H18C109.5
C4A—C5A—H5A120.8H18A—C18A—H18C109.5
C4B—C5B—C6B119.4 (5)H18B—C18A—H18C109.5
C4B—C5B—H5B120.3N8B—C18B—H18D109.5
C6B—C5B—H5B120.3N8B—C18B—H18E109.5
C1A—C6A—C5A117.1 (6)H18D—C18B—H18E109.5
C1A—C6A—C7A119.3 (6)N8B—C18B—H18F109.5
C5A—C6A—C7A123.6 (5)H18D—C18B—H18F109.5
C1B—C6B—C5B117.1 (5)H18E—C18B—H18F109.5
C1B—C6B—C7B118.9 (5)O1A—C19A—N8A124.4 (7)
C5B—C6B—C7B124.0 (4)O1A—C19A—O2A124.1 (6)
N1A—C7A—C6A115.4 (4)N8A—C19A—O2A111.5 (5)
N1A—C7A—H7A1108.4O1B—C19B—O2B126.0 (5)
C6A—C7A—H7A1108.4O1B—C19B—N8B122.9 (5)
N1A—C7A—H7A2108.4O2B—C19B—N8B111.0 (4)
C6A—C7A—H7A2108.4O2A—C20A—H20A109.5
H7A1—C7A—H7A2107.5O2A—C20A—H20B109.5
N1B—C7B—C6B113.8 (4)H20A—C20A—H20B109.5
N1B—C7B—H7B1108.8O2A—C20A—H20C109.5
C6B—C7B—H7B1108.8H20A—C20A—H20C109.5
N1B—C7B—H7B2108.8H20B—C20A—H20C109.5
C6B—C7B—H7B2108.8O2B—C20B—H20D109.5
H7B1—C7B—H7B2107.7O2B—C20B—H20E109.5
N2A—C8A—N1A124.9 (4)H20D—C20B—H20E109.5
N2A—C8A—C12A128.2 (5)O2B—C20B—H20F109.5
N1A—C8A—C12A106.9 (4)H20D—C20B—H20F109.5
N2B—C8B—N1B124.6 (4)H20E—C20B—H20F109.5
N2B—C8B—C12B128.9 (5)C8A—N1A—N3A110.9 (4)
N1B—C8B—C12B106.4 (4)C8A—N1A—C7A129.0 (4)
N2A—C9A—C10A125.5 (5)N3A—N1A—C7A120.1 (4)
N2A—C9A—H9A117.3N3B—N1B—C8B110.9 (4)
C10A—C9A—H9A117.3N3B—N1B—C7B121.0 (4)
N2B—C9B—C10B125.5 (5)C8B—N1B—C7B128.0 (4)
N2B—C9B—H9B117.2C8A—N2A—C9A112.2 (4)
C10B—C9B—H9B117.2C8B—N2B—C9B111.5 (4)
C9A—C10A—C11A121.0 (5)C13A—N3A—N1A106.5 (4)
C9A—C10A—H10A119.5C13B—N3B—N1B107.2 (4)
C11A—C10A—H10A119.5C14A—N4A—C15A114.0 (4)
C11B—C10B—C9B120.7 (5)C14B—N4B—C15B116.3 (4)
C11B—C10B—H10B119.6C14A—N5A—C17A115.7 (4)
C9B—C10B—H10B119.6C14B—N5B—C17B116.0 (4)
C10A—C11A—C12A116.1 (5)C15A—N6A—H6A1120.0
C10A—C11A—H11A122.0C15A—N6A—H6A2120.0
C12A—C11A—H11A122.0H6A1—N6A—H6A2120.0
C10B—C11B—C12B116.6 (5)C15B—N6B—H6B1120.0
C10B—C11B—H11B121.7C15B—N6B—H6B2120.0
C12B—C11B—H11B121.7H6B1—N6B—H6B2120.0
C11A—C12A—C8A117.0 (4)C17A—N7A—H7A3120.0
C11A—C12A—C13A137.9 (4)C17A—N7A—H7A4120.0
C8A—C12A—C13A105.1 (4)H7A3—N7A—H7A4120.0
C11B—C12B—C8B116.9 (4)C17B—N7B—H7B3120.0
C11B—C12B—C13B137.7 (5)C17B—N7B—H7B4120.0
C8B—C12B—C13B105.4 (4)H7B3—N7B—H7B4120.0
N3A—C13A—C12A110.6 (4)C19A—N8A—C16A122.2 (5)
N3A—C13A—C14A119.0 (4)C19A—N8A—C18A119.7 (5)
C12A—C13A—C14A130.4 (4)C16A—N8A—C18A117.3 (5)
N3B—C13B—C12B110.1 (4)C19B—N8B—C16B122.0 (4)
N3B—C13B—C14B120.8 (4)C19B—N8B—C18B120.3 (4)
C12B—C13B—C14B129.1 (4)C16B—N8B—C18B117.2 (4)
N5A—C14A—N4A129.1 (4)C19A—O2A—C20A115.2 (5)
N5A—C14A—C13A116.4 (4)C19B—O2B—C20B114.9 (5)
F1A—C1A—C2A—C3A179.6 (6)C15A—C16A—C17A—N5A0.7 (8)
C6A—C1A—C2A—C3A2.0 (10)N8A—C16A—C17A—N5A179.8 (4)
F1B—C1B—C2B—C3B179.5 (5)C15B—C16B—C17B—N7B177.9 (5)
C6B—C1B—C2B—C3B0.7 (8)N8B—C16B—C17B—N7B1.7 (7)
C1A—C2A—C3A—C4A0.1 (12)C15B—C16B—C17B—N5B2.1 (7)
C1B—C2B—C3B—C4B0.8 (9)N8B—C16B—C17B—N5B178.2 (4)
C2A—C3A—C4A—C5A1.7 (12)N2A—C8A—N1A—N3A178.4 (5)
C2B—C3B—C4B—C5B0.5 (9)C12A—C8A—N1A—N3A0.2 (5)
C3A—C4A—C5A—C6A1.7 (10)N2A—C8A—N1A—C7A0.5 (8)
C3B—C4B—C5B—C6B0.1 (8)C12A—C8A—N1A—C7A177.7 (5)
F1A—C1A—C6A—C5A179.6 (5)C6A—C7A—N1A—C8A105.3 (6)
C2A—C1A—C6A—C5A1.9 (8)C6A—C7A—N1A—N3A77.0 (6)
F1A—C1A—C6A—C7A0.5 (8)N2B—C8B—N1B—N3B178.6 (4)
C2A—C1A—C6A—C7A178.9 (5)C12B—C8B—N1B—N3B0.9 (5)
C4A—C5A—C6A—C1A0.1 (8)N2B—C8B—N1B—C7B1.9 (8)
C4A—C5A—C6A—C7A179.2 (5)C12B—C8B—N1B—C7B175.8 (4)
F1B—C1B—C6B—C5B179.2 (4)C6B—C7B—N1B—N3B76.7 (6)
C2B—C1B—C6B—C5B0.3 (7)C6B—C7B—N1B—C8B107.0 (6)
F1B—C1B—C6B—C7B0.3 (7)N1A—C8A—N2A—C9A177.9 (5)
C2B—C1B—C6B—C7B179.1 (5)C12A—C8A—N2A—C9A0.1 (8)
C4B—C5B—C6B—C1B0.0 (7)C10A—C9A—N2A—C8A0.5 (9)
C4B—C5B—C6B—C7B179.4 (5)N1B—C8B—N2B—C9B177.0 (5)
C1A—C6A—C7A—N1A170.1 (5)C12B—C8B—N2B—C9B0.1 (8)
C5A—C6A—C7A—N1A10.8 (7)C10B—C9B—N2B—C8B0.4 (8)
C1B—C6B—C7B—N1B170.4 (4)C12A—C13A—N3A—N1A0.1 (6)
C5B—C6B—C7B—N1B9.0 (7)C14A—C13A—N3A—N1A178.5 (4)
N2A—C9A—C10A—C11A0.2 (10)C8A—N1A—N3A—C13A0.0 (6)
N2B—C9B—C10B—C11B0.3 (10)C7A—N1A—N3A—C13A178.1 (4)
C9A—C10A—C11A—C12A0.7 (8)C12B—C13B—N3B—N1B1.0 (5)
C9B—C10B—C11B—C12B0.2 (8)C14B—C13B—N3B—N1B177.7 (4)
C10A—C11A—C12A—C8A1.1 (7)C8B—N1B—N3B—C13B1.2 (5)
C10A—C11A—C12A—C13A177.8 (6)C7B—N1B—N3B—C13B175.7 (4)
N2A—C8A—C12A—C11A0.9 (8)N5A—C14A—N4A—C15A2.1 (8)
N1A—C8A—C12A—C11A179.0 (4)C13A—C14A—N4A—C15A177.0 (4)
N2A—C8A—C12A—C13A178.4 (5)N6A—C15A—N4A—C14A179.6 (4)
N1A—C8A—C12A—C13A0.2 (5)C16A—C15A—N4A—C14A2.0 (7)
C10B—C11B—C12B—C8B0.6 (7)N5B—C14B—N4B—C15B4.8 (7)
C10B—C11B—C12B—C13B176.6 (6)C13B—C14B—N4B—C15B178.4 (4)
N2B—C8B—C12B—C11B0.6 (8)N6B—C15B—N4B—C14B178.6 (4)
N1B—C8B—C12B—C11B177.0 (4)C16B—C15B—N4B—C14B1.8 (7)
N2B—C8B—C12B—C13B177.8 (5)N4A—C14A—N5A—C17A0.7 (8)
N1B—C8B—C12B—C13B0.2 (5)C13A—C14A—N5A—C17A178.3 (4)
C11A—C12A—C13A—N3A178.8 (6)N7A—C17A—N5A—C14A178.6 (4)
C8A—C12A—C13A—N3A0.2 (6)C16A—C17A—N5A—C14A0.8 (7)
C11A—C12A—C13A—C14A2.7 (10)N4B—C14B—N5B—C17B4.1 (7)
C8A—C12A—C13A—C14A178.3 (5)C13B—C14B—N5B—C17B179.1 (4)
C11B—C12B—C13B—N3B176.8 (6)N7B—C17B—N5B—C14B179.6 (4)
C8B—C12B—C13B—N3B0.5 (5)C16B—C17B—N5B—C14B0.3 (7)
C11B—C12B—C13B—C14B6.9 (10)O1A—C19A—N8A—C16A171.3 (5)
C8B—C12B—C13B—C14B176.8 (5)O2A—C19A—N8A—C16A7.5 (6)
N3A—C13A—C14A—N5A0.8 (7)O1A—C19A—N8A—C18A2.1 (8)
C12A—C13A—C14A—N5A177.6 (5)O2A—C19A—N8A—C18A176.6 (4)
N3A—C13A—C14A—N4A180.0 (4)C15A—C16A—N8A—C19A100.4 (6)
C12A—C13A—C14A—N4A1.6 (8)C17A—C16A—N8A—C19A80.1 (6)
N3B—C13B—C14B—N4B177.1 (4)C15A—C16A—N8A—C18A90.2 (6)
C12B—C13B—C14B—N4B1.2 (8)C17A—C16A—N8A—C18A89.2 (6)
N3B—C13B—C14B—N5B5.7 (7)O1B—C19B—N8B—C16B170.4 (4)
C12B—C13B—C14B—N5B178.4 (4)O2B—C19B—N8B—C16B10.1 (6)
N6A—C15A—C16A—C17A178.2 (5)O1B—C19B—N8B—C18B1.6 (7)
N4A—C15A—C16A—C17A0.7 (8)O2B—C19B—N8B—C18B177.9 (4)
N6A—C15A—C16A—N8A1.3 (8)C17B—C16B—N8B—C19B89.8 (6)
N4A—C15A—C16A—N8A178.8 (5)C15B—C16B—N8B—C19B90.6 (6)
N6B—C15B—C16B—C17B178.3 (5)C17B—C16B—N8B—C18B82.4 (6)
N4B—C15B—C16B—C17B1.4 (7)C15B—C16B—N8B—C18B97.2 (6)
N6B—C15B—C16B—N8B1.4 (8)O1A—C19A—O2A—C20A1.8 (8)
N4B—C15B—C16B—N8B179.0 (4)N8A—C19A—O2A—C20A176.9 (5)
C15A—C16A—C17A—N7A178.6 (5)O1B—C19B—O2B—C20B0.1 (7)
N8A—C16A—C17A—N7A0.9 (8)N8B—C19B—O2B—C20B179.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N6A—H6A2···O1Bi0.862.203.041 (5)167
N6B—H6B2···O1Ai0.862.102.928 (6)162
N7A—H7A3···N5Bii0.862.122.975 (5)174
N7B—H7B3···N5Aii0.862.112.966 (5)172
N6A—H6A1···O1B0.862.513.280 (6)149
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1.
 

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