Comparison of the crystal structures and thermochemistry of a novel soluble guanylate cyclase stimulator riociguat and its solvates

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.

Computing details

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)

Crystal data

C20H19FN8O2	Z = 2
Mr = 422.43	F(000) = 440
Triclinic, P1	Dx = 1.388 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0917 (5) Å	Cell parameters from 6412 reflections
b = 10.8937 (6) Å	θ = 3.2–27.5°
c = 11.7949 (6) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Rigaku RAXIS-RAPID/ZJUG diffractometer	3959 independent reflections
Radiation source: rotating anode	2679 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
Detector resolution: 10.00 pixels mm^-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −9→9
Absorption correction: multi-scan Higashi, T. (1995)	k = −13→13
Tmin = 0.953, Tmax = 0.978	l = −13→14
8817 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.046	H-atom parameters constrained
wR(F^2) = 0.143	w = 1/[σ^2(Fo^2) + (0.0449P)^2 + 0.9981P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
3959 reflections	Δρmax = 0.29 e Å^−3
283 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.086 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6416 (3)	0.8715 (2)	0.0487 (2)	0.0439 (6)
C2	0.6040 (4)	0.8303 (3)	−0.0516 (2)	0.0526 (7)
H2	0.6809	0.8259	−0.1181	0.063*
C3	0.4500 (4)	0.7957 (3)	−0.0514 (2)	0.0599 (8)
H3	0.4218	0.7669	−0.1184	0.072*
C4	0.3364 (4)	0.8034 (3)	0.0476 (3)	0.0620 (8)
H4	0.2320	0.7799	0.0473	0.074*
C5	0.3781 (4)	0.8464 (3)	0.1475 (2)	0.0531 (7)
H5	0.3011	0.8513	0.2140	0.064*
C6	0.5319 (3)	0.8818 (2)	0.1498 (2)	0.0412 (6)
C7	0.5854 (3)	0.9304 (3)	0.2549 (2)	0.0455 (6)
H7A	0.6910	0.8776	0.2708	0.055*
H7B	0.6071	1.0141	0.2392	0.055*
C8	0.3434 (3)	1.0333 (2)	0.4005 (2)	0.0402 (6)
C9	0.1970 (4)	1.2272 (3)	0.4173 (3)	0.0620 (8)
H9	0.1738	1.3095	0.3916	0.074*
C10	0.0990 (4)	1.1971 (3)	0.5178 (3)	0.0580 (7)
H10	0.0154	1.2584	0.5558	0.070*
C11	0.1266 (3)	1.0770 (2)	0.5601 (2)	0.0461 (6)
H11	0.0625	1.0547	0.6261	0.055*
C12	0.2550 (3)	0.9900 (2)	0.49948 (19)	0.0385 (5)
C13	0.3295 (3)	0.8602 (2)	0.50550 (19)	0.0352 (5)
C14	0.2862 (3)	0.7667 (2)	0.59160 (19)	0.0370 (5)
C15	0.1427 (3)	0.7264 (2)	0.7634 (2)	0.0391 (6)
C16	0.2017 (3)	0.5998 (2)	0.7461 (2)	0.0427 (6)
C17	0.3084 (4)	0.5617 (2)	0.6457 (2)	0.0477 (7)
C18	0.2877 (4)	0.4684 (3)	0.9109 (3)	0.0626 (8)
H18A	0.2410	0.4179	0.9701	0.094*
H18B	0.3139	0.5404	0.9443	0.094*
H18C	0.3894	0.4203	0.8705	0.094*
C19	0.0289 (4)	0.4529 (3)	0.8334 (2)	0.0545 (7)
C20	−0.2189 (5)	0.4511 (5)	0.7473 (4)	0.1053 (15)
H20A	−0.1919	0.3614	0.7502	0.158*
H20B	−0.2635	0.4772	0.6772	0.158*
H20C	−0.3023	0.4817	0.8110	0.158*
F1	0.7939 (2)	0.90673 (16)	0.05006 (13)	0.0595 (5)
N1	0.4605 (3)	0.93410 (18)	0.35544 (16)	0.0406 (5)
N2	0.3193 (3)	1.1491 (2)	0.35593 (19)	0.0516 (6)
N3	0.4522 (3)	0.82834 (18)	0.41847 (16)	0.0405 (5)
N4	0.1850 (3)	0.81212 (18)	0.68472 (16)	0.0386 (5)
N5	0.3524 (3)	0.64679 (18)	0.56675 (17)	0.0455 (5)
N6	0.0411 (3)	0.7716 (2)	0.85934 (18)	0.0530 (6)
H6A	0.0068	0.8510	0.8680	0.064*
H6B	0.0108	0.7210	0.9118	0.064*
N7	0.3715 (4)	0.4406 (2)	0.6228 (2)	0.0787 (10)
H7C	0.4371	0.4194	0.5601	0.094*
H7D	0.3464	0.3840	0.6708	0.094*
N8	0.1640 (3)	0.5088 (2)	0.83140 (18)	0.0492 (6)
O1	−0.0017 (3)	0.3709 (2)	0.90020 (19)	0.0736 (7)
O2	−0.0681 (3)	0.5005 (2)	0.7527 (2)	0.0724 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0510 (15)	0.0419 (14)	0.0378 (13)	−0.0103 (11)	−0.0018 (11)	0.0062 (11)
C2	0.071 (2)	0.0478 (15)	0.0361 (13)	−0.0081 (14)	−0.0036 (13)	0.0019 (12)
C3	0.091 (2)	0.0520 (17)	0.0419 (15)	−0.0182 (16)	−0.0203 (15)	0.0051 (13)
C4	0.077 (2)	0.0660 (19)	0.0549 (17)	−0.0362 (16)	−0.0200 (16)	0.0078 (15)
C5	0.0621 (18)	0.0597 (17)	0.0428 (14)	−0.0286 (14)	−0.0028 (13)	0.0080 (13)
C6	0.0541 (15)	0.0380 (12)	0.0337 (12)	−0.0165 (11)	−0.0045 (11)	0.0086 (10)
C7	0.0540 (16)	0.0508 (15)	0.0343 (12)	−0.0224 (12)	0.0017 (11)	0.0072 (11)
C8	0.0507 (15)	0.0400 (13)	0.0332 (12)	−0.0160 (11)	−0.0082 (11)	0.0050 (10)
C9	0.079 (2)	0.0423 (15)	0.0658 (19)	−0.0096 (15)	−0.0194 (17)	0.0121 (14)
C10	0.0605 (18)	0.0460 (15)	0.0643 (18)	−0.0007 (13)	−0.0110 (15)	0.0009 (14)
C11	0.0463 (15)	0.0488 (15)	0.0433 (14)	−0.0099 (12)	−0.0059 (12)	0.0013 (12)
C12	0.0430 (14)	0.0406 (13)	0.0338 (12)	−0.0129 (10)	−0.0052 (10)	0.0013 (10)
C13	0.0414 (13)	0.0348 (12)	0.0304 (11)	−0.0115 (10)	−0.0028 (10)	0.0023 (9)
C14	0.0401 (13)	0.0369 (12)	0.0334 (12)	−0.0114 (10)	0.0028 (10)	0.0017 (10)
C15	0.0367 (13)	0.0450 (13)	0.0340 (12)	−0.0096 (10)	0.0036 (10)	0.0034 (10)
C16	0.0481 (15)	0.0388 (13)	0.0380 (13)	−0.0128 (11)	0.0109 (11)	0.0050 (10)
C17	0.0554 (16)	0.0393 (13)	0.0452 (14)	−0.0153 (12)	0.0145 (12)	0.0002 (11)
C18	0.0609 (19)	0.0634 (19)	0.0574 (17)	−0.0047 (15)	0.0000 (15)	0.0166 (15)
C19	0.0574 (17)	0.0488 (15)	0.0519 (16)	−0.0123 (13)	0.0132 (14)	0.0103 (13)
C20	0.088 (3)	0.136 (4)	0.111 (3)	−0.070 (3)	−0.018 (3)	0.028 (3)
F1	0.0505 (10)	0.0751 (11)	0.0509 (9)	−0.0156 (8)	0.0053 (7)	0.0022 (8)
N1	0.0551 (13)	0.0389 (11)	0.0298 (10)	−0.0195 (10)	0.0012 (9)	0.0058 (8)
N2	0.0709 (16)	0.0405 (12)	0.0461 (12)	−0.0154 (11)	−0.0131 (11)	0.0115 (10)
N3	0.0511 (12)	0.0379 (11)	0.0331 (10)	−0.0151 (9)	0.0016 (9)	0.0049 (8)
N4	0.0425 (11)	0.0377 (10)	0.0336 (10)	−0.0087 (9)	0.0034 (9)	0.0030 (8)
N5	0.0577 (14)	0.0356 (11)	0.0407 (11)	−0.0169 (10)	0.0139 (10)	0.0010 (9)
N6	0.0623 (15)	0.0479 (13)	0.0399 (12)	−0.0051 (11)	0.0171 (11)	0.0027 (10)
N7	0.112 (2)	0.0345 (12)	0.0717 (17)	−0.0122 (13)	0.0496 (16)	0.0024 (12)
N8	0.0493 (13)	0.0476 (12)	0.0461 (12)	−0.0104 (10)	0.0092 (10)	0.0132 (10)
O1	0.0830 (16)	0.0598 (13)	0.0751 (14)	−0.0266 (11)	0.0134 (12)	0.0262 (11)
O2	0.0666 (14)	0.0824 (15)	0.0765 (15)	−0.0372 (12)	−0.0122 (12)	0.0310 (13)

Geometric parameters (Å, º)

C1—F1	1.362 (3)	C13—C14	1.475 (3)
C1—C2	1.369 (4)	C14—N4	1.325 (3)
C1—C6	1.382 (3)	C14—N5	1.337 (3)
C2—C3	1.369 (4)	C15—N6	1.351 (3)
C2—H2	0.9300	C15—N4	1.357 (3)
C3—C4	1.381 (4)	C15—C16	1.380 (3)
C3—H3	0.9300	C16—C17	1.392 (3)
C4—C5	1.386 (4)	C16—N8	1.438 (3)
C4—H4	0.9300	C17—N7	1.340 (3)
C5—C6	1.376 (4)	C17—N5	1.357 (3)
C5—H5	0.9300	C18—N8	1.459 (4)
C6—C7	1.508 (3)	C18—H18A	0.9600
C7—N1	1.448 (3)	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—O1	1.214 (3)
C8—N2	1.342 (3)	C19—O2	1.343 (4)
C8—N1	1.360 (3)	C19—N8	1.348 (4)
C8—C12	1.405 (3)	C20—O2	1.435 (4)
C9—N2	1.320 (4)	C20—H20A	0.9600
C9—C10	1.404 (4)	C20—H20B	0.9600
C9—H9	0.9300	C20—H20C	0.9600
C10—C11	1.374 (4)	N1—N3	1.361 (3)
C10—H10	0.9300	N6—H6A	0.8600
C11—C12	1.396 (4)	N6—H6B	0.8600
C11—H11	0.9300	N7—H7C	0.8600
C12—C13	1.429 (3)	N7—H7D	0.8600
C13—N3	1.332 (3)
F1—C1—C2	119.0 (2)	N4—C14—C13	115.7 (2)
F1—C1—C6	117.4 (2)	N5—C14—C13	116.6 (2)
C2—C1—C6	123.6 (3)	N6—C15—N4	116.5 (2)
C3—C2—C1	118.2 (3)	N6—C15—C16	122.1 (2)
C3—C2—H2	120.9	N4—C15—C16	121.4 (2)
C1—C2—H2	120.9	C15—C16—C17	118.2 (2)
C2—C3—C4	120.4 (3)	C15—C16—N8	121.8 (2)
C2—C3—H3	119.8	C17—C16—N8	119.9 (2)
C4—C3—H3	119.8	N7—C17—N5	117.4 (2)
C3—C4—C5	119.9 (3)	N7—C17—C16	121.8 (2)
C3—C4—H4	120.0	N5—C17—C16	120.8 (2)
C5—C4—H4	120.0	N8—C18—H18A	109.5
C6—C5—C4	120.9 (3)	N8—C18—H18B	109.5
C6—C5—H5	119.5	H18A—C18—H18B	109.5
C4—C5—H5	119.5	N8—C18—H18C	109.5
C5—C6—C1	117.0 (2)	H18A—C18—H18C	109.5
C5—C6—C7	123.9 (2)	H18B—C18—H18C	109.5
C1—C6—C7	119.1 (2)	O1—C19—O2	124.4 (3)
N1—C7—C6	113.6 (2)	O1—C19—N8	124.3 (3)
N1—C7—H7A	108.8	O2—C19—N8	111.3 (2)
C6—C7—H7A	108.8	O2—C20—H20A	109.5
N1—C7—H7B	108.8	O2—C20—H20B	109.5
C6—C7—H7B	108.8	H20A—C20—H20B	109.5
H7A—C7—H7B	107.7	O2—C20—H20C	109.5
N2—C8—N1	125.2 (2)	H20A—C20—H20C	109.5
N2—C8—C12	127.9 (2)	H20B—C20—H20C	109.5
N1—C8—C12	106.9 (2)	C8—N1—N3	111.57 (18)
N2—C9—C10	125.9 (3)	C8—N1—C7	128.6 (2)
N2—C9—H9	117.1	N3—N1—C7	119.8 (2)
C10—C9—H9	117.1	C9—N2—C8	112.4 (2)
C11—C10—C9	119.9 (3)	C13—N3—N1	106.47 (19)
C11—C10—H10	120.0	C14—N4—C15	115.9 (2)
C9—C10—H10	120.0	C14—N5—C17	116.0 (2)
C10—C11—C12	117.1 (2)	C15—N6—H6A	120.0
C10—C11—H11	121.5	C15—N6—H6B	120.0
C12—C11—H11	121.5	H6A—N6—H6B	120.0
C11—C12—C8	116.8 (2)	C17—N7—H7C	120.0
C11—C12—C13	138.8 (2)	C17—N7—H7D	120.0
C8—C12—C13	104.4 (2)	H7C—N7—H7D	120.0
N3—C13—C12	110.63 (19)	C19—N8—C16	122.5 (2)
N3—C13—C14	120.9 (2)	C19—N8—C18	119.9 (2)
C12—C13—C14	128.5 (2)	C16—N8—C18	117.4 (2)
N4—C14—N5	127.7 (2)	C19—O2—C20	117.0 (3)
F1—C1—C2—C3	−179.7 (2)	N8—C16—C17—N7	3.5 (5)
C6—C1—C2—C3	−1.0 (4)	C15—C16—C17—N5	−0.4 (4)
C1—C2—C3—C4	0.4 (4)	N8—C16—C17—N5	−176.6 (2)
C2—C3—C4—C5	0.0 (5)	N2—C8—N1—N3	−178.6 (2)
C3—C4—C5—C6	0.1 (5)	C12—C8—N1—N3	0.8 (3)
C4—C5—C6—C1	−0.5 (4)	N2—C8—N1—C7	2.0 (4)
C4—C5—C6—C7	179.5 (3)	C12—C8—N1—C7	−178.6 (2)
F1—C1—C6—C5	179.8 (2)	C6—C7—N1—C8	−98.7 (3)
C2—C1—C6—C5	1.0 (4)	C6—C7—N1—N3	82.0 (3)
F1—C1—C6—C7	−0.2 (3)	C10—C9—N2—C8	−0.4 (4)
C2—C1—C6—C7	−179.0 (2)	N1—C8—N2—C9	180.0 (3)
C5—C6—C7—N1	1.2 (4)	C12—C8—N2—C9	0.7 (4)
C1—C6—C7—N1	−178.8 (2)	C12—C13—N3—N1	0.2 (3)
N2—C9—C10—C11	−0.2 (5)	C14—C13—N3—N1	180.0 (2)
C9—C10—C11—C12	0.6 (4)	C8—N1—N3—C13	−0.6 (3)
C10—C11—C12—C8	−0.3 (4)	C7—N1—N3—C13	178.9 (2)
C10—C11—C12—C13	−179.0 (3)	N5—C14—N4—C15	−0.6 (4)
N2—C8—C12—C11	−0.3 (4)	C13—C14—N4—C15	179.0 (2)
N1—C8—C12—C11	−179.7 (2)	N6—C15—N4—C14	179.3 (2)
N2—C8—C12—C13	178.8 (2)	C16—C15—N4—C14	−0.4 (4)
N1—C8—C12—C13	−0.6 (3)	N4—C14—N5—C17	1.1 (4)
C11—C12—C13—N3	179.1 (3)	C13—C14—N5—C17	−178.6 (2)
C8—C12—C13—N3	0.3 (3)	N7—C17—N5—C14	179.4 (3)
C11—C12—C13—C14	−0.7 (5)	C16—C17—N5—C14	−0.5 (4)
C8—C12—C13—C14	−179.5 (2)	O1—C19—N8—C16	175.8 (3)
N3—C13—C14—N4	168.3 (2)	O2—C19—N8—C16	−4.7 (4)
C12—C13—C14—N4	−11.9 (4)	O1—C19—N8—C18	2.0 (4)
N3—C13—C14—N5	−12.0 (3)	O2—C19—N8—C18	−178.6 (2)
C12—C13—C14—N5	167.8 (2)	C15—C16—N8—C19	92.4 (3)
N6—C15—C16—C17	−178.8 (3)	C17—C16—N8—C19	−91.4 (3)
N4—C15—C16—C17	0.8 (4)	C15—C16—N8—C18	−93.5 (3)
N6—C15—C16—N8	−2.6 (4)	C17—C16—N8—C18	82.6 (3)
N4—C15—C16—N8	177.0 (2)	O1—C19—O2—C20	0.9 (5)
C15—C16—C17—N7	179.7 (3)	N8—C19—O2—C20	−178.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7C···N5^i	0.86	2.14	2.977 (3)	165

Symmetry code: (i) −x+1, −y+1, −z+1.

(III)

Crystal data

C20H19FN8O2·C2H3N	Z = 2
Mr = 463.49	F(000) = 484
Triclinic, P1	Dx = 1.308 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4657 (5) Å	Cell parameters from 6092 reflections
b = 11.4408 (8) Å	θ = 3.0–27.4°
c = 13.1812 (9) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Rigaku RAXIS-RAPID/ZJUG diffractometer	4151 independent reflections
Radiation source: rotating anode	2576 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
Detector resolution: 10.00 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −10→8
Absorption correction: multi-scan Higashi, T. (1995)	k = −13→13
Tmin = 0.951, Tmax = 0.972	l = −15→15
9234 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.160	w = 1/[σ^2(Fo^2) + (0.0598P)^2 + 0.7424P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
4151 reflections	Δρmax = 0.46 e Å^−3
310 parameters	Δρmin = −0.29 e Å^−3
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.075 (5)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5906 (4)	0.1716 (3)	0.0115 (2)	0.0682 (9)
C2	0.6798 (5)	0.0812 (4)	−0.0608 (3)	0.0877 (12)
H2	0.6750	0.0664	−0.1353	0.105*
C3	0.7763 (5)	0.0128 (4)	−0.0217 (3)	0.0904 (12)
H3	0.8369	−0.0480	−0.0697	0.108*
C4	0.7820 (4)	0.0354 (3)	0.0886 (3)	0.0808 (10)
H4	0.8473	−0.0098	0.1154	0.097*
C5	0.6900 (4)	0.1261 (3)	0.1604 (2)	0.0657 (8)
H5	0.6941	0.1400	0.2347	0.079*
C6	0.5918 (3)	0.1966 (3)	0.1229 (2)	0.0555 (7)
C7	0.4882 (4)	0.2988 (3)	0.1951 (2)	0.0628 (8)
H7A	0.5314	0.3809	0.1988	0.075*
H7B	0.3827	0.2840	0.1608	0.075*
C8	0.3445 (3)	0.2665 (3)	0.3518 (2)	0.0509 (7)
C9	0.0915 (4)	0.1932 (3)	0.3654 (3)	0.0739 (10)
H9	−0.0085	0.1583	0.3346	0.089*
C10	0.1201 (4)	0.2202 (3)	0.4771 (3)	0.0733 (9)
H10	0.0401	0.2040	0.5184	0.088*
C11	0.2700 (3)	0.2719 (3)	0.5269 (2)	0.0613 (8)
H11	0.2902	0.2894	0.6010	0.074*
C12	0.3896 (3)	0.2968 (3)	0.46272 (19)	0.0482 (7)
C13	0.5534 (3)	0.3514 (2)	0.47514 (19)	0.0481 (7)
C14	0.6653 (3)	0.3991 (2)	0.57354 (19)	0.0474 (7)
C15	0.7094 (4)	0.4292 (3)	0.7535 (2)	0.0549 (7)
C16	0.8677 (3)	0.4771 (3)	0.74990 (19)	0.0507 (7)
C17	0.9173 (3)	0.4866 (2)	0.65239 (19)	0.0467 (6)
C18	0.9902 (5)	0.6538 (3)	0.9138 (2)	0.0842 (11)
H18A	1.0689	0.6704	0.9718	0.126*
H18B	0.8892	0.6765	0.9449	0.126*
H18C	1.0187	0.7031	0.8712	0.126*
C19	1.0931 (4)	0.4439 (4)	0.8565 (2)	0.0673 (9)
C20	1.1770 (6)	0.2355 (5)	0.7921 (3)	0.1103 (15)
H20A	1.1482	0.1527	0.7375	0.166*
H20B	1.1743	0.2322	0.8638	0.166*
H20C	1.2819	0.2631	0.7802	0.166*
C21	0.7068 (7)	0.0664 (5)	0.5111 (6)	0.134 (2)
C22	0.6968 (9)	0.0894 (5)	0.6310 (5)	0.164 (3)
H22A	0.5944	0.0584	0.6441	0.246*
H22B	0.7125	0.1787	0.6740	0.246*
H22C	0.7772	0.0459	0.6515	0.246*
F1	0.4935 (3)	0.2395 (2)	−0.02641 (14)	0.0997 (7)
N1	0.4762 (3)	0.3026 (2)	0.30596 (16)	0.0567 (6)
N2	0.2006 (3)	0.2147 (2)	0.29956 (19)	0.0637 (7)
N3	0.6034 (3)	0.3550 (2)	0.38040 (16)	0.0543 (6)
N4	0.6040 (3)	0.3893 (2)	0.66409 (16)	0.0548 (6)
N5	0.8142 (3)	0.4460 (2)	0.56229 (16)	0.0486 (6)
N6	0.6498 (3)	0.4182 (3)	0.84490 (19)	0.0819 (9)
H6A	0.5537	0.3883	0.8434	0.098*
H6B	0.7082	0.4411	0.9042	0.098*
N7	1.0661 (3)	0.5347 (2)	0.64376 (18)	0.0616 (7)
H7C	1.0935	0.5392	0.5827	0.074*
H7D	1.1322	0.5605	0.6994	0.074*
N8	0.9805 (3)	0.5196 (2)	0.84349 (17)	0.0609 (7)
N9	0.7051 (9)	0.0442 (6)	0.4170 (5)	0.190 (3)
O1	1.2058 (3)	0.4791 (3)	0.92485 (19)	0.0973 (9)
O2	1.0656 (3)	0.3241 (2)	0.78450 (17)	0.0760 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0627 (19)	0.093 (2)	0.0381 (16)	−0.0059 (17)	−0.0049 (14)	0.0150 (16)
C2	0.082 (2)	0.111 (3)	0.0412 (18)	−0.013 (2)	0.0086 (17)	−0.0006 (19)
C3	0.074 (2)	0.083 (3)	0.075 (3)	−0.005 (2)	0.013 (2)	−0.012 (2)
C4	0.066 (2)	0.075 (2)	0.084 (3)	0.0084 (18)	−0.0007 (18)	0.011 (2)
C5	0.0632 (19)	0.074 (2)	0.0512 (17)	0.0060 (16)	−0.0029 (14)	0.0141 (16)
C6	0.0497 (16)	0.0708 (19)	0.0336 (14)	−0.0033 (14)	−0.0063 (12)	0.0077 (13)
C7	0.0645 (18)	0.088 (2)	0.0317 (14)	0.0147 (17)	−0.0063 (12)	0.0178 (14)
C8	0.0512 (16)	0.0549 (17)	0.0366 (14)	0.0144 (13)	−0.0040 (12)	0.0051 (12)
C9	0.0526 (18)	0.094 (3)	0.063 (2)	0.0055 (17)	−0.0080 (16)	0.0161 (18)
C10	0.0565 (19)	0.095 (3)	0.064 (2)	0.0040 (18)	0.0034 (15)	0.0263 (19)
C11	0.0646 (19)	0.072 (2)	0.0425 (15)	0.0108 (16)	0.0025 (14)	0.0159 (14)
C12	0.0559 (16)	0.0509 (16)	0.0312 (13)	0.0128 (13)	−0.0031 (11)	0.0071 (12)
C13	0.0591 (17)	0.0509 (16)	0.0293 (13)	0.0089 (13)	−0.0040 (11)	0.0092 (11)
C14	0.0619 (17)	0.0439 (15)	0.0318 (13)	0.0059 (13)	−0.0068 (12)	0.0094 (11)
C15	0.077 (2)	0.0543 (17)	0.0322 (14)	−0.0103 (15)	−0.0095 (13)	0.0179 (12)
C16	0.0720 (19)	0.0499 (16)	0.0281 (13)	−0.0066 (14)	−0.0125 (12)	0.0146 (12)
C17	0.0602 (17)	0.0440 (15)	0.0335 (13)	−0.0001 (13)	−0.0069 (11)	0.0130 (11)
C18	0.127 (3)	0.069 (2)	0.0438 (17)	−0.028 (2)	−0.0169 (18)	0.0139 (16)
C19	0.076 (2)	0.093 (3)	0.0414 (16)	−0.0160 (19)	−0.0139 (15)	0.0388 (18)
C20	0.137 (4)	0.129 (4)	0.083 (3)	0.049 (3)	−0.002 (2)	0.055 (3)
C21	0.138 (5)	0.080 (3)	0.183 (6)	−0.002 (3)	0.009 (5)	0.049 (4)
C22	0.282 (8)	0.099 (4)	0.106 (4)	0.035 (5)	−0.005 (5)	0.029 (3)
F1	0.1128 (16)	0.143 (2)	0.0474 (11)	0.0136 (15)	−0.0110 (10)	0.0412 (12)
N1	0.0552 (14)	0.0782 (17)	0.0290 (11)	0.0075 (12)	−0.0081 (10)	0.0119 (11)
N2	0.0543 (14)	0.0769 (18)	0.0465 (13)	0.0109 (13)	−0.0083 (12)	0.0083 (12)
N3	0.0594 (14)	0.0662 (15)	0.0317 (11)	0.0049 (12)	−0.0080 (10)	0.0128 (11)
N4	0.0703 (15)	0.0601 (15)	0.0310 (11)	−0.0083 (12)	−0.0078 (10)	0.0164 (10)
N5	0.0593 (14)	0.0518 (13)	0.0315 (11)	0.0044 (11)	−0.0076 (10)	0.0129 (10)
N6	0.092 (2)	0.116 (2)	0.0375 (13)	−0.0418 (17)	−0.0178 (13)	0.0373 (15)
N7	0.0672 (16)	0.0801 (18)	0.0359 (12)	−0.0107 (13)	−0.0118 (11)	0.0234 (12)
N8	0.0825 (17)	0.0607 (15)	0.0365 (12)	−0.0162 (13)	−0.0186 (11)	0.0192 (11)
N9	0.274 (8)	0.155 (5)	0.161 (5)	0.041 (5)	0.072 (6)	0.075 (5)
O1	0.0976 (18)	0.139 (2)	0.0609 (14)	−0.0233 (16)	−0.0388 (13)	0.0502 (15)
O2	0.0936 (17)	0.0793 (16)	0.0575 (13)	0.0077 (13)	−0.0177 (12)	0.0296 (12)

Geometric parameters (Å, º)

C1—F1	1.374 (4)	C14—N5	1.372 (3)
C1—C2	1.384 (5)	C15—N6	1.360 (3)
C1—C6	1.384 (4)	C15—N4	1.378 (3)
C2—C3	1.384 (5)	C15—C16	1.425 (4)
C2—H2	0.9300	C16—C17	1.400 (4)
C3—C4	1.375 (5)	C16—N8	1.456 (3)
C3—H3	0.9300	C17—N7	1.368 (3)
C4—C5	1.397 (4)	C17—N5	1.373 (3)
C4—H4	0.9300	C18—N8	1.456 (4)
C5—C6	1.399 (4)	C18—H18A	0.9600
C5—H5	0.9300	C18—H18B	0.9600
C6—C7	1.531 (4)	C18—H18C	0.9600
C7—N1	1.451 (3)	C19—O1	1.238 (3)
C7—H7A	0.9700	C19—O2	1.340 (4)
C7—H7B	0.9700	C19—N8	1.376 (4)
C8—N2	1.373 (3)	C20—O2	1.455 (4)
C8—N1	1.391 (4)	C20—H20A	0.9600
C8—C12	1.408 (3)	C20—H20B	0.9600
C9—N2	1.352 (4)	C20—H20C	0.9600
C9—C10	1.398 (4)	C21—N9	1.167 (7)
C9—H9	0.9300	C21—C22	1.505 (7)
C10—C11	1.406 (4)	C22—H22A	0.9600
C10—H10	0.9300	C22—H22B	0.9600
C11—C12	1.413 (4)	C22—H22C	0.9600
C11—H11	0.9300	N1—N3	1.386 (3)
C12—C13	1.466 (4)	N6—H6A	0.8600
C13—N3	1.340 (3)	N6—H6B	0.8600
C13—C14	1.496 (3)	N7—H7C	0.8600
C14—N4	1.350 (3)	N7—H7D	0.8600
F1—C1—C2	120.2 (3)	N4—C15—C16	122.7 (2)
F1—C1—C6	117.1 (3)	C17—C16—C15	118.7 (2)
C2—C1—C6	122.7 (3)	C17—C16—N8	117.8 (3)
C3—C2—C1	119.6 (3)	C15—C16—N8	123.4 (2)
C3—C2—H2	120.2	N7—C17—N5	118.8 (2)
C1—C2—H2	120.2	N7—C17—C16	122.0 (2)
C4—C3—C2	119.6 (3)	N5—C17—C16	119.2 (3)
C4—C3—H3	120.2	N8—C18—H18A	109.5
C2—C3—H3	120.2	N8—C18—H18B	109.5
C3—C4—C5	120.1 (4)	H18A—C18—H18B	109.5
C3—C4—H4	119.9	N8—C18—H18C	109.5
C5—C4—H4	119.9	H18A—C18—H18C	109.5
C4—C5—C6	121.3 (3)	H18B—C18—H18C	109.5
C4—C5—H5	119.3	O1—C19—O2	123.2 (3)
C6—C5—H5	119.3	O1—C19—N8	125.8 (3)
C1—C6—C5	116.7 (3)	O2—C19—N8	111.0 (2)
C1—C6—C7	118.1 (3)	O2—C20—H20A	109.5
C5—C6—C7	125.2 (2)	O2—C20—H20B	109.5
N1—C7—C6	113.7 (2)	H20A—C20—H20B	109.5
N1—C7—H7A	108.8	O2—C20—H20C	109.5
C6—C7—H7A	108.8	H20A—C20—H20C	109.5
N1—C7—H7B	108.8	H20B—C20—H20C	109.5
C6—C7—H7B	108.8	N9—C21—C22	175.6 (8)
H7A—C7—H7B	107.7	C21—C22—H22A	109.5
N2—C8—N1	126.8 (2)	C21—C22—H22B	109.5
N2—C8—C12	127.8 (3)	H22A—C22—H22B	109.5
N1—C8—C12	105.4 (2)	C21—C22—H22C	109.5
N2—C9—C10	123.8 (3)	H22A—C22—H22C	109.5
N2—C9—H9	118.1	H22B—C22—H22C	109.5
C10—C9—H9	118.1	N3—N1—C8	113.4 (2)
C9—C10—C11	120.0 (3)	N3—N1—C7	119.1 (2)
C9—C10—H10	120.0	C8—N1—C7	127.4 (2)
C11—C10—H10	120.0	C9—N2—C8	114.2 (2)
C10—C11—C12	119.1 (3)	C13—N3—N1	104.9 (2)
C10—C11—H11	120.5	C14—N4—C15	113.7 (2)
C12—C11—H11	120.5	C14—N5—C17	117.5 (2)
C8—C12—C11	115.1 (3)	C15—N6—H6A	120.0
C8—C12—C13	105.1 (2)	C15—N6—H6B	120.0
C11—C12—C13	139.7 (2)	H6A—N6—H6B	120.0
N3—C13—C12	111.2 (2)	C17—N7—H7C	120.0
N3—C13—C14	118.7 (2)	C17—N7—H7D	120.0
C12—C13—C14	130.1 (2)	H7C—N7—H7D	120.0
N4—C14—N5	128.1 (2)	C19—N8—C18	119.4 (3)
N4—C14—C13	113.9 (2)	C19—N8—C16	122.5 (2)
N5—C14—C13	118.0 (2)	C18—N8—C16	117.2 (2)
N6—C15—N4	114.3 (3)	C19—O2—C20	115.5 (3)
N6—C15—C16	123.0 (2)
F1—C1—C2—C3	−179.6 (3)	N8—C16—C17—N7	−0.4 (4)
C6—C1—C2—C3	−0.7 (5)	C15—C16—C17—N5	−2.0 (4)
C1—C2—C3—C4	0.1 (6)	N8—C16—C17—N5	179.4 (2)
C2—C3—C4—C5	0.5 (6)	N2—C8—N1—N3	178.5 (2)
C3—C4—C5—C6	−0.6 (5)	C12—C8—N1—N3	−0.3 (3)
F1—C1—C6—C5	179.5 (3)	N2—C8—N1—C7	3.0 (5)
C2—C1—C6—C5	0.6 (5)	C12—C8—N1—C7	−175.8 (3)
F1—C1—C6—C7	−1.1 (4)	C6—C7—N1—N3	75.5 (3)
C2—C1—C6—C7	180.0 (3)	C6—C7—N1—C8	−109.3 (3)
C4—C5—C6—C1	0.1 (5)	C10—C9—N2—C8	−0.1 (5)
C4—C5—C6—C7	−179.3 (3)	N1—C8—N2—C9	−177.6 (3)
C1—C6—C7—N1	169.9 (3)	C12—C8—N2—C9	1.0 (4)
C5—C6—C7—N1	−10.8 (4)	C12—C13—N3—N1	−0.7 (3)
N2—C9—C10—C11	−0.6 (5)	C14—C13—N3—N1	178.7 (2)
C9—C10—C11—C12	0.6 (5)	C8—N1—N3—C13	0.6 (3)
N2—C8—C12—C11	−1.0 (4)	C7—N1—N3—C13	176.5 (2)
N1—C8—C12—C11	177.8 (2)	N5—C14—N4—C15	−1.9 (4)
N2—C8—C12—C13	−178.9 (3)	C13—C14—N4—C15	177.8 (2)
N1—C8—C12—C13	−0.1 (3)	N6—C15—N4—C14	−179.1 (2)
C10—C11—C12—C8	0.1 (4)	C16—C15—N4—C14	0.4 (4)
C10—C11—C12—C13	177.0 (3)	N4—C14—N5—C17	1.4 (4)
C8—C12—C13—N3	0.5 (3)	C13—C14—N5—C17	−178.3 (2)
C11—C12—C13—N3	−176.6 (3)	N7—C17—N5—C14	−179.5 (2)
C8—C12—C13—C14	−178.8 (3)	C16—C17—N5—C14	0.7 (4)
C11—C12—C13—C14	4.2 (5)	O1—C19—N8—C18	0.4 (5)
N3—C13—C14—N4	−179.0 (2)	O2—C19—N8—C18	−179.6 (3)
C12—C13—C14—N4	0.2 (4)	O1—C19—N8—C16	169.3 (3)
N3—C13—C14—N5	0.7 (4)	O2—C19—N8—C16	−10.8 (4)
C12—C13—C14—N5	180.0 (2)	C17—C16—N8—C19	−83.2 (3)
N6—C15—C16—C17	−179.1 (3)	C15—C16—N8—C19	98.2 (3)
N4—C15—C16—C17	1.4 (4)	C17—C16—N8—C18	85.9 (3)
N6—C15—C16—N8	−0.5 (5)	C15—C16—N8—C18	−92.7 (3)
N4—C15—C16—N8	180.0 (3)	O1—C19—O2—C20	0.7 (5)
C15—C16—C17—N7	178.2 (3)	N8—C19—O2—C20	−179.3 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6B···O1^i	0.86	2.18	3.012 (3)	164
N7—H7C···N5^ii	0.86	2.14	2.995 (3)	174

Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+2, −y+1, −z+1.

(IV)

Crystal data

2(C20H19FN8O2)·C3H7NO	Z = 2
Mr = 917.94	F(000) = 960
Triclinic, P1	Dx = 1.359 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.6703 (7) Å	Cell parameters from 10475 reflections
b = 13.4220 (9) Å	θ = 3.1–27.4°
c = 16.9095 (12) Å	µ = 0.10 mm^−1
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) Å^3

Data collection

Rigaku RAXIS-RAPID/ZJUG diffractometer	7763 independent reflections
Radiation source: rotating anode	3928 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 10.00 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −12→12
Absorption correction: multi-scan Higashi, T. (1995)	k = −15→15
Tmin = 0.965, Tmax = 0.984	l = −17→20
17506 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.085	H-atom parameters constrained
wR(F^2) = 0.231	w = 1/[σ^2(Fo^2) + (0.0932P)^2 + 2.0768P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
7763 reflections	Δρmax = 0.52 e Å^−3
604 parameters	Δρmin = −0.43 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0094 (16)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.6582 (8)	0.9293 (7)	0.6363 (6)	0.129 (3)
C1B	−0.2536 (5)	0.2261 (5)	0.8555 (4)	0.0778 (16)
C1C	0.2173 (6)	0.7487 (5)	0.5421 (5)	0.0874 (18)
H1C	0.2617	0.7048	0.5799	0.105*
C2A	0.7052 (9)	0.9547 (9)	0.6921 (8)	0.159 (2)
H2A	0.7212	1.0234	0.6860	0.191*
C2B	−0.2716 (6)	0.2163 (6)	0.7814 (5)	0.102 (2)
H2B	−0.2952	0.1535	0.7777	0.123*
C2C	0.0199 (7)	0.7044 (7)	0.6500 (5)	0.129 (3)
H2C1	−0.0442	0.6647	0.6435	0.194*
H2C2	−0.0225	0.7535	0.6816	0.194*
H2C3	0.0781	0.6587	0.6799	0.194*
C3A	0.7297 (8)	0.8795 (9)	0.7582 (6)	0.136 (2)
H3A	0.7639	0.8960	0.7980	0.163*
C3B	−0.2546 (6)	0.2995 (7)	0.7128 (5)	0.101 (2)
H3B	−0.2671	0.2945	0.6617	0.121*
C3C	0.0211 (7)	0.8311 (6)	0.5128 (6)	0.137 (3)
H3C1	0.0762	0.8507	0.4567	0.206*
H3C2	−0.0062	0.8917	0.5337	0.206*
H3C3	−0.0538	0.7990	0.5115	0.206*
C4A	0.7033 (8)	0.7732 (8)	0.7678 (6)	0.144 (3)
H4A	0.7183	0.7209	0.8140	0.172*
C4B	−0.2191 (5)	0.3906 (6)	0.7196 (4)	0.0865 (18)
H4B	−0.2061	0.4476	0.6726	0.104*
C5A	0.6545 (6)	0.7510 (8)	0.7057 (6)	0.114 (2)
H5A	0.6379	0.6831	0.7096	0.137*
C5B	−0.2023 (4)	0.3988 (4)	0.7953 (3)	0.0661 (13)
H5B	−0.1789	0.4617	0.7989	0.079*
C6A	0.6313 (5)	0.8311 (5)	0.6382 (5)	0.088 (2)
C6B	−0.2193 (4)	0.3167 (4)	0.8654 (3)	0.0538 (12)
C7A	0.5794 (5)	0.8165 (4)	0.5698 (4)	0.0816 (18)
H7A1	0.4899	0.8437	0.5771	0.098*
H7A2	0.6288	0.8565	0.5159	0.098*
C7B	−0.2012 (5)	0.3173 (4)	0.9509 (3)	0.0650 (14)
H7B1	−0.2712	0.2807	0.9946	0.078*
H7B2	−0.1202	0.2795	0.9585	0.078*
C8A	0.6811 (4)	0.6556 (3)	0.5254 (3)	0.0514 (11)
C8B	−0.2901 (4)	0.4689 (3)	1.0135 (3)	0.0491 (11)
C9A	0.8724 (5)	0.6235 (5)	0.4435 (3)	0.0743 (15)
H9A	0.9533	0.6442	0.4090	0.089*
C9B	−0.4704 (5)	0.4929 (5)	1.1092 (3)	0.0731 (15)
H9B	−0.5493	0.4706	1.1459	0.088*
C10A	0.8435 (5)	0.5209 (4)	0.4575 (3)	0.0742 (15)
H10A	0.9036	0.4768	0.4313	0.089*
C10B	−0.4340 (5)	0.5904 (4)	1.1052 (3)	0.0716 (15)
H10B	−0.4881	0.6303	1.1387	0.086*
C11A	0.7281 (4)	0.4840 (4)	0.5092 (3)	0.0599 (13)
H11A	0.7078	0.4153	0.5192	0.072*
C11B	−0.3193 (4)	0.6284 (4)	1.0526 (3)	0.0604 (13)
H11B	−0.2941	0.6937	1.0494	0.072*
C12A	0.6427 (4)	0.5536 (3)	0.5459 (3)	0.0459 (10)
C12B	−0.2418 (4)	0.5655 (3)	1.0038 (3)	0.0467 (11)
C13A	0.5180 (4)	0.5542 (3)	0.6042 (3)	0.0457 (10)
C13B	−0.1190 (4)	0.5663 (3)	0.9448 (3)	0.0439 (10)
C14A	0.4356 (4)	0.4661 (3)	0.6501 (3)	0.0427 (10)
C14B	−0.0247 (4)	0.6482 (3)	0.9089 (3)	0.0449 (10)
C15A	0.4101 (4)	0.2933 (3)	0.6748 (3)	0.0458 (10)
C15B	0.0324 (4)	0.8098 (3)	0.8999 (3)	0.0545 (12)
C16A	0.2978 (4)	0.3016 (3)	0.7367 (3)	0.0465 (11)
C16B	0.1452 (4)	0.7965 (3)	0.8404 (3)	0.0560 (12)
C17A	0.2564 (4)	0.3999 (3)	0.7493 (3)	0.0484 (11)
C17B	0.1676 (4)	0.7027 (3)	0.8182 (3)	0.0517 (11)
C18A	0.1051 (4)	0.2001 (4)	0.7588 (3)	0.0678 (14)
H18A	0.0636	0.1389	0.7963	0.102*
H18B	0.1301	0.1924	0.7018	0.102*
H18C	0.0458	0.2593	0.7611	0.102*
C18B	0.3469 (5)	0.8659 (4)	0.8473 (3)	0.0681 (14)
H18D	0.4098	0.9165	0.8146	0.102*
H18E	0.3880	0.7976	0.8534	0.102*
H18F	0.3113	0.8781	0.9023	0.102*
C19A	0.2472 (4)	0.1474 (3)	0.8542 (3)	0.0545 (12)
C19B	0.2437 (6)	0.9420 (4)	0.7331 (4)	0.0789 (17)
C20A	0.3939 (6)	0.0996 (5)	0.9424 (4)	0.100 (2)
H20A	0.3173	0.0852	0.9880	0.149*
H20B	0.4545	0.1327	0.9587	0.149*
H20C	0.4331	0.0358	0.9301	0.149*
C20B	0.1348 (9)	1.0015 (6)	0.6209 (5)	0.149 (3)
H20D	0.1359	1.0727	0.6216	0.224*
H20E	0.0560	0.9907	0.6078	0.224*
H20F	0.2082	0.9854	0.5787	0.224*
F1A	0.6286 (7)	1.0075 (4)	0.5705 (5)	0.215 (3)
F1B	−0.2708 (4)	0.1430 (3)	0.9239 (3)	0.1223 (14)
N1A	0.5835 (3)	0.7095 (3)	0.5670 (3)	0.0618 (11)
N1B	−0.1989 (4)	0.4201 (3)	0.9623 (2)	0.0546 (10)
N1C	0.0920 (4)	0.7590 (4)	0.5679 (3)	0.0811 (13)
N2A	0.7939 (4)	0.6944 (3)	0.4755 (3)	0.0689 (12)
N2B	−0.4012 (4)	0.4286 (3)	1.0644 (2)	0.0638 (11)
N3A	0.4853 (3)	0.6472 (3)	0.6160 (2)	0.0575 (10)
N3B	−0.0948 (3)	0.4789 (3)	0.9212 (2)	0.0545 (10)
N4A	0.4812 (3)	0.3774 (3)	0.6310 (2)	0.0478 (9)
N4B	−0.0545 (3)	0.7339 (3)	0.9361 (2)	0.0511 (9)
N5A	0.3263 (3)	0.4840 (3)	0.7054 (2)	0.0466 (9)
N5B	0.0823 (3)	0.6265 (3)	0.8527 (2)	0.0481 (9)
N6A	0.4565 (3)	0.2042 (3)	0.6546 (2)	0.0623 (11)
H6A1	0.5272	0.2029	0.6160	0.075*
H6A2	0.4157	0.1482	0.6803	0.075*
N6B	0.0041 (4)	0.8980 (3)	0.9263 (3)	0.0763 (14)
H6B1	−0.0660	0.9040	0.9642	0.092*
H6B2	0.0563	0.9481	0.9052	0.092*
N7A	0.1448 (3)	0.4165 (3)	0.8046 (2)	0.0614 (11)
H7A3	0.1215	0.4781	0.8104	0.074*
H7A4	0.0967	0.3654	0.8342	0.074*
N7B	0.2739 (4)	0.6835 (3)	0.7604 (2)	0.0678 (12)
H7B3	0.2848	0.6251	0.7472	0.081*
H7B4	0.3313	0.7295	0.7365	0.081*
N8A	0.2201 (3)	0.2146 (3)	0.7846 (2)	0.0507 (9)
N8B	0.2422 (4)	0.8743 (3)	0.8040 (3)	0.0707 (13)
O1A	0.1783 (3)	0.0763 (2)	0.9001 (2)	0.0676 (10)
O1B	0.3286 (4)	1.0048 (3)	0.6990 (3)	0.1186 (18)
O1C	0.2814 (5)	0.7915 (4)	0.4729 (4)	0.1256 (18)
O2A	0.3589 (3)	0.1671 (2)	0.8682 (2)	0.0651 (9)
O2B	0.1413 (4)	0.9356 (3)	0.7022 (3)	0.0907 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.141 (7)	0.083 (6)	0.148 (8)	−0.043 (5)	0.037 (6)	−0.059 (5)
C1B	0.087 (4)	0.079 (4)	0.077 (4)	−0.026 (3)	−0.008 (3)	−0.037 (3)
C1C	0.068 (4)	0.079 (4)	0.113 (5)	0.003 (3)	0.000 (3)	−0.044 (4)
C2A	0.167 (7)	0.164	0.171	−0.065	0.008 (6)	−0.104 (5)
C2B	0.113 (5)	0.116 (6)	0.103 (6)	−0.026 (4)	−0.026 (4)	−0.062 (5)
C2C	0.096 (5)	0.179 (8)	0.106 (6)	−0.022 (5)	0.008 (4)	−0.051 (6)
C3A	0.141 (7)	0.170	0.132	0.007	−0.040 (5)	−0.094 (4)
C3B	0.092 (4)	0.151 (7)	0.086 (5)	−0.004 (4)	−0.033 (4)	−0.064 (5)
C3C	0.123 (6)	0.108 (6)	0.194 (9)	−0.005 (5)	−0.075 (6)	−0.024 (6)
C4A	0.134 (7)	0.151 (9)	0.158	0.025 (6)	−0.034 (6)	−0.075 (6)
C4B	0.081 (4)	0.118 (6)	0.071 (4)	0.004 (3)	−0.030 (3)	−0.033 (4)
C5A	0.091 (5)	0.151 (8)	0.117 (6)	−0.001 (5)	−0.024 (4)	−0.066 (6)
C5B	0.067 (3)	0.071 (4)	0.063 (3)	−0.004 (3)	−0.014 (2)	−0.023 (3)
C6A	0.060 (3)	0.074 (4)	0.128 (6)	−0.022 (3)	0.023 (4)	−0.058 (4)
C6B	0.051 (3)	0.060 (3)	0.056 (3)	−0.012 (2)	−0.004 (2)	−0.028 (3)
C7A	0.077 (4)	0.031 (3)	0.115 (5)	−0.012 (2)	0.013 (3)	−0.013 (3)
C7B	0.089 (4)	0.048 (3)	0.057 (3)	−0.031 (3)	−0.003 (2)	−0.015 (2)
C8A	0.045 (3)	0.046 (3)	0.056 (3)	−0.008 (2)	−0.006 (2)	−0.005 (2)
C8B	0.055 (3)	0.049 (3)	0.042 (3)	−0.014 (2)	−0.008 (2)	−0.009 (2)
C9A	0.054 (3)	0.081 (4)	0.071 (4)	−0.010 (3)	0.011 (2)	−0.013 (3)
C9B	0.054 (3)	0.092 (4)	0.066 (3)	−0.018 (3)	0.008 (2)	−0.023 (3)
C10A	0.065 (3)	0.074 (4)	0.071 (4)	−0.005 (3)	0.012 (3)	−0.025 (3)
C10B	0.060 (3)	0.079 (4)	0.074 (4)	−0.006 (3)	0.002 (3)	−0.032 (3)
C11A	0.061 (3)	0.055 (3)	0.058 (3)	−0.004 (2)	−0.001 (2)	−0.018 (2)
C11B	0.055 (3)	0.062 (3)	0.064 (3)	−0.007 (2)	−0.005 (2)	−0.024 (3)
C12A	0.053 (3)	0.038 (3)	0.045 (3)	−0.0042 (19)	−0.011 (2)	−0.008 (2)
C12B	0.054 (3)	0.047 (3)	0.042 (2)	−0.013 (2)	−0.011 (2)	−0.011 (2)
C13A	0.048 (2)	0.033 (2)	0.053 (3)	−0.0031 (18)	−0.010 (2)	−0.007 (2)
C13B	0.051 (2)	0.036 (2)	0.043 (2)	−0.0090 (18)	−0.0050 (19)	−0.011 (2)
C14A	0.048 (2)	0.036 (2)	0.044 (2)	−0.0065 (18)	−0.0111 (19)	−0.007 (2)
C14B	0.054 (3)	0.037 (2)	0.045 (3)	−0.0088 (19)	−0.009 (2)	−0.012 (2)
C15A	0.047 (2)	0.040 (3)	0.049 (3)	−0.0062 (19)	−0.0070 (19)	−0.013 (2)
C15B	0.062 (3)	0.034 (3)	0.061 (3)	−0.012 (2)	0.004 (2)	−0.015 (2)
C16A	0.048 (2)	0.033 (2)	0.053 (3)	−0.0101 (18)	0.001 (2)	−0.009 (2)
C16B	0.065 (3)	0.039 (3)	0.058 (3)	−0.020 (2)	0.008 (2)	−0.016 (2)
C17A	0.045 (2)	0.042 (3)	0.057 (3)	−0.0093 (19)	−0.008 (2)	−0.014 (2)
C17B	0.056 (3)	0.042 (3)	0.054 (3)	−0.013 (2)	0.003 (2)	−0.017 (2)
C18A	0.056 (3)	0.055 (3)	0.091 (4)	−0.019 (2)	−0.015 (3)	−0.012 (3)
C18B	0.060 (3)	0.068 (3)	0.085 (4)	−0.009 (2)	−0.014 (3)	−0.035 (3)
C19A	0.062 (3)	0.038 (3)	0.060 (3)	−0.005 (2)	0.001 (2)	−0.021 (2)
C19B	0.090 (4)	0.048 (3)	0.086 (4)	−0.010 (3)	0.013 (3)	−0.027 (3)
C20A	0.130 (5)	0.072 (4)	0.102 (5)	−0.016 (4)	−0.061 (4)	0.004 (4)
C20B	0.250 (10)	0.104 (6)	0.087 (5)	−0.041 (6)	−0.062 (6)	0.019 (5)
F1A	0.294 (7)	0.085 (4)	0.231 (7)	−0.084 (4)	0.055 (6)	−0.066 (4)
F1B	0.198 (4)	0.071 (2)	0.109 (3)	−0.060 (3)	−0.026 (3)	−0.029 (2)
N1A	0.055 (2)	0.040 (2)	0.078 (3)	−0.0120 (18)	0.005 (2)	−0.009 (2)
N1B	0.070 (2)	0.045 (2)	0.050 (2)	−0.0217 (18)	0.0000 (18)	−0.0177 (18)
N1C	0.069 (3)	0.085 (4)	0.097 (4)	0.000 (2)	−0.019 (3)	−0.036 (3)
N2A	0.058 (2)	0.060 (3)	0.076 (3)	−0.019 (2)	0.002 (2)	−0.006 (2)
N2B	0.061 (2)	0.074 (3)	0.052 (2)	−0.028 (2)	−0.0001 (19)	−0.012 (2)
N3A	0.051 (2)	0.038 (2)	0.071 (3)	−0.0115 (17)	0.0029 (18)	−0.0066 (19)
N3B	0.059 (2)	0.049 (2)	0.053 (2)	−0.0238 (18)	0.0041 (17)	−0.0183 (19)
N4A	0.045 (2)	0.039 (2)	0.056 (2)	−0.0087 (16)	−0.0028 (16)	−0.0127 (17)
N4B	0.055 (2)	0.040 (2)	0.056 (2)	−0.0132 (16)	0.0014 (17)	−0.0193 (18)
N5A	0.048 (2)	0.037 (2)	0.052 (2)	−0.0077 (15)	−0.0013 (17)	−0.0152 (17)
N5B	0.054 (2)	0.037 (2)	0.051 (2)	−0.0112 (16)	0.0003 (17)	−0.0155 (17)
N6A	0.064 (2)	0.043 (2)	0.071 (3)	−0.0115 (18)	0.0117 (19)	−0.024 (2)
N6B	0.078 (3)	0.051 (3)	0.091 (3)	−0.025 (2)	0.026 (2)	−0.038 (2)
N7A	0.057 (2)	0.042 (2)	0.076 (3)	−0.0103 (17)	0.0143 (19)	−0.024 (2)
N7B	0.074 (3)	0.046 (2)	0.075 (3)	−0.0207 (19)	0.019 (2)	−0.028 (2)
N8A	0.052 (2)	0.035 (2)	0.061 (3)	−0.0099 (16)	−0.0058 (18)	−0.0112 (19)
N8B	0.089 (3)	0.046 (2)	0.063 (3)	−0.016 (2)	0.019 (2)	−0.020 (2)
O1A	0.078 (2)	0.046 (2)	0.067 (2)	−0.0236 (17)	0.0075 (17)	−0.0097 (16)
O1B	0.114 (3)	0.063 (3)	0.145 (4)	−0.050 (2)	0.047 (3)	−0.029 (3)
O1C	0.108 (3)	0.087 (3)	0.146 (4)	−0.008 (3)	0.033 (3)	−0.031 (3)
O2A	0.072 (2)	0.052 (2)	0.072 (2)	−0.0157 (16)	−0.0205 (17)	−0.0093 (17)
O2B	0.114 (3)	0.076 (3)	0.081 (3)	−0.030 (2)	−0.029 (2)	−0.003 (2)

Geometric parameters (Å, º)

C1A—C2A	1.313 (12)	C11B—C12B	1.394 (6)
C1A—C6A	1.372 (9)	C11B—H11B	0.9300
C1A—F1A	1.378 (11)	C12A—C13A	1.433 (5)
C1B—F1B	1.356 (7)	C12B—C13B	1.422 (5)
C1B—C2B	1.360 (8)	C13A—N3A	1.312 (5)
C1B—C6B	1.374 (7)	C13A—C14A	1.466 (5)
C1C—O1C	1.211 (7)	C13B—N3B	1.317 (5)
C1C—N1C	1.297 (7)	C13B—C14B	1.469 (5)
C1C—H1C	0.9300	C14A—N4A	1.324 (5)
C2A—C3A	1.343 (13)	C14A—N5A	1.334 (5)
C2A—H2A	0.9300	C14B—N4B	1.329 (5)
C2B—C3B	1.359 (9)	C14B—N5B	1.341 (5)
C2B—H2B	0.9300	C15A—N6A	1.338 (5)
C2C—N1C	1.437 (8)	C15A—N4A	1.357 (5)
C2C—H2C1	0.9600	C15A—C16A	1.385 (5)
C2C—H2C2	0.9600	C15B—N6B	1.354 (5)
C2C—H2C3	0.9600	C15B—N4B	1.360 (5)
C3A—C4A	1.443 (11)	C15B—C16B	1.380 (6)
C3A—H3A	0.9300	C16A—C17A	1.397 (6)
C3B—C4B	1.364 (9)	C16A—N8A	1.434 (5)
C3B—H3B	0.9300	C16B—C17B	1.389 (6)
C3C—N1C	1.441 (8)	C16B—N8B	1.450 (5)
C3C—H3C1	0.9600	C17A—N7A	1.346 (5)
C3C—H3C2	0.9600	C17A—N5A	1.351 (5)
C3C—H3C3	0.9600	C17B—N7B	1.341 (5)
C4A—C5A	1.399 (10)	C17B—N5B	1.350 (5)
C4A—H4A	0.9300	C18A—N8A	1.455 (5)
C4B—C5B	1.373 (7)	C18A—H18A	0.9600
C4B—H4B	0.9300	C18A—H18B	0.9600
C5A—C6A	1.388 (9)	C18A—H18C	0.9600
C5A—H5A	0.9300	C18B—N8B	1.466 (6)
C5B—C6B	1.364 (7)	C18B—H18D	0.9600
C5B—H5B	0.9300	C18B—H18E	0.9600
C6A—C7A	1.473 (9)	C18B—H18F	0.9600
C6B—C7B	1.509 (6)	C19A—O1A	1.228 (5)
C7A—N1A	1.444 (6)	C19A—O2A	1.342 (5)
C7A—H7A1	0.9700	C19A—N8A	1.347 (6)
C7A—H7A2	0.9700	C19B—O1B	1.225 (6)
C7B—N1B	1.449 (5)	C19B—N8B	1.285 (7)
C7B—H7B1	0.9700	C19B—O2B	1.349 (7)
C7B—H7B2	0.9700	C20A—O2A	1.440 (6)
C8A—N2A	1.343 (5)	C20A—H20A	0.9600
C8A—N1A	1.351 (5)	C20A—H20B	0.9600
C8A—C12A	1.399 (6)	C20A—H20C	0.9600
C8B—N2B	1.340 (5)	C20B—O2B	1.427 (7)
C8B—N1B	1.360 (5)	C20B—H20D	0.9600
C8B—C12B	1.403 (5)	C20B—H20E	0.9600
C9A—N2A	1.327 (6)	C20B—H20F	0.9600
C9A—C10A	1.388 (7)	N1A—N3A	1.360 (4)
C9A—H9A	0.9300	N1B—N3B	1.356 (4)
C9B—N2B	1.335 (6)	N6A—H6A1	0.8600
C9B—C10B	1.387 (7)	N6A—H6A2	0.8600
C9B—H9B	0.9300	N6B—H6B1	0.8600
C10A—C11A	1.366 (6)	N6B—H6B2	0.8600
C10A—H10A	0.9300	N7A—H7A3	0.8600
C10B—C11B	1.369 (6)	N7A—H7A4	0.8600
C10B—H10B	0.9300	N7B—H7B3	0.8600
C11A—C12A	1.384 (6)	N7B—H7B4	0.8600
C11A—H11A	0.9300
C2A—C1A—C6A	126.1 (11)	C12A—C13A—C14A	127.8 (4)
C2A—C1A—F1A	118.3 (9)	N3B—C13B—C12B	110.7 (3)
C6A—C1A—F1A	115.6 (9)	N3B—C13B—C14B	119.8 (3)
F1B—C1B—C2B	118.9 (6)	C12B—C13B—C14B	129.5 (4)
F1B—C1B—C6B	117.6 (5)	N4A—C14A—N5A	128.2 (3)
C2B—C1B—C6B	123.5 (6)	N4A—C14A—C13A	114.6 (3)
O1C—C1C—N1C	125.5 (7)	N5A—C14A—C13A	117.2 (4)
O1C—C1C—H1C	117.2	N4B—C14B—N5B	127.9 (3)
N1C—C1C—H1C	117.2	N4B—C14B—C13B	116.7 (3)
C1A—C2A—C3A	118.7 (10)	N5B—C14B—C13B	115.4 (4)
C1A—C2A—H2A	120.7	N6A—C15A—N4A	115.7 (3)
C3A—C2A—H2A	120.7	N6A—C15A—C16A	123.5 (4)
C3B—C2B—C1B	119.0 (6)	N4A—C15A—C16A	120.8 (4)
C3B—C2B—H2B	120.5	N6B—C15B—N4B	116.7 (4)
C1B—C2B—H2B	120.5	N6B—C15B—C16B	121.7 (4)
N1C—C2C—H2C1	109.5	N4B—C15B—C16B	121.6 (4)
N1C—C2C—H2C2	109.5	C15A—C16A—C17A	118.1 (4)
H2C1—C2C—H2C2	109.5	C15A—C16A—N8A	122.5 (4)
N1C—C2C—H2C3	109.5	C17A—C16A—N8A	119.3 (3)
H2C1—C2C—H2C3	109.5	C15B—C16B—C17B	117.9 (4)
H2C2—C2C—H2C3	109.5	C15B—C16B—N8B	122.5 (4)
C2A—C3A—C4A	120.3 (8)	C17B—C16B—N8B	119.5 (4)
C2A—C3A—H3A	119.9	N7A—C17A—N5A	116.4 (4)
C4A—C3A—H3A	119.9	N7A—C17A—C16A	122.3 (4)
C2B—C3B—C4B	119.4 (6)	N5A—C17A—C16A	121.3 (4)
C2B—C3B—H3B	120.3	N7B—C17B—N5B	116.4 (4)
C4B—C3B—H3B	120.3	N7B—C17B—C16B	121.9 (4)
N1C—C3C—H3C1	109.5	N5B—C17B—C16B	121.7 (4)
N1C—C3C—H3C2	109.5	N8A—C18A—H18A	109.5
H3C1—C3C—H3C2	109.5	N8A—C18A—H18B	109.5
N1C—C3C—H3C3	109.5	H18A—C18A—H18B	109.5
H3C1—C3C—H3C3	109.5	N8A—C18A—H18C	109.5
H3C2—C3C—H3C3	109.5	H18A—C18A—H18C	109.5
C5A—C4A—C3A	118.3 (9)	H18B—C18A—H18C	109.5
C5A—C4A—H4A	120.9	N8B—C18B—H18D	109.5
C3A—C4A—H4A	120.9	N8B—C18B—H18E	109.5
C3B—C4B—C5B	120.4 (6)	H18D—C18B—H18E	109.5
C3B—C4B—H4B	119.8	N8B—C18B—H18F	109.5
C5B—C4B—H4B	119.8	H18D—C18B—H18F	109.5
C6A—C5A—C4A	119.5 (9)	H18E—C18B—H18F	109.5
C6A—C5A—H5A	120.3	O1A—C19A—O2A	123.5 (5)
C4A—C5A—H5A	120.3	O1A—C19A—N8A	124.3 (4)
C6B—C5B—C4B	121.5 (5)	O2A—C19A—N8A	112.1 (4)
C6B—C5B—H5B	119.2	O1B—C19B—N8B	123.0 (7)
C4B—C5B—H5B	119.2	O1B—C19B—O2B	124.9 (6)
C1A—C6A—C5A	117.2 (9)	N8B—C19B—O2B	112.2 (5)
C1A—C6A—C7A	118.9 (8)	O2A—C20A—H20A	109.5
C5A—C6A—C7A	123.9 (6)	O2A—C20A—H20B	109.5
C5B—C6B—C1B	116.1 (5)	H20A—C20A—H20B	109.5
C5B—C6B—C7B	125.6 (4)	O2A—C20A—H20C	109.5
C1B—C6B—C7B	118.3 (5)	H20A—C20A—H20C	109.5
N1A—C7A—C6A	113.9 (5)	H20B—C20A—H20C	109.5
N1A—C7A—H7A1	108.8	O2B—C20B—H20D	109.5
C6A—C7A—H7A1	108.8	O2B—C20B—H20E	109.5
N1A—C7A—H7A2	108.8	H20D—C20B—H20E	109.5
C6A—C7A—H7A2	108.8	O2B—C20B—H20F	109.5
H7A1—C7A—H7A2	107.7	H20D—C20B—H20F	109.5
N1B—C7B—C6B	114.2 (4)	H20E—C20B—H20F	109.5
N1B—C7B—H7B1	108.7	C8A—N1A—N3A	111.3 (3)
C6B—C7B—H7B1	108.7	C8A—N1A—C7A	128.2 (4)
N1B—C7B—H7B2	108.7	N3A—N1A—C7A	120.3 (4)
C6B—C7B—H7B2	108.7	N3B—N1B—C8B	111.5 (3)
H7B1—C7B—H7B2	107.6	N3B—N1B—C7B	120.4 (4)
N2A—C8A—N1A	125.3 (4)	C8B—N1B—C7B	128.1 (4)
N2A—C8A—C12A	127.6 (4)	C1C—N1C—C2C	123.4 (6)
N1A—C8A—C12A	107.1 (4)	C1C—N1C—C3C	118.7 (6)
N2B—C8B—N1B	125.3 (4)	C2C—N1C—C3C	117.9 (6)
N2B—C8B—C12B	128.3 (4)	C9A—N2A—C8A	112.2 (4)
N1B—C8B—C12B	106.4 (3)	C9B—N2B—C8B	112.3 (4)
N2A—C9A—C10A	125.3 (4)	C13A—N3A—N1A	107.0 (3)
N2A—C9A—H9A	117.4	C13B—N3B—N1B	106.8 (3)
C10A—C9A—H9A	117.4	C14A—N4A—C15A	116.1 (3)
N2B—C9B—C10B	125.2 (4)	C14B—N4B—C15B	115.6 (3)
N2B—C9B—H9B	117.4	C14A—N5A—C17A	115.4 (3)
C10B—C9B—H9B	117.4	C14B—N5B—C17B	115.4 (3)
C11A—C10A—C9A	120.8 (5)	C15A—N6A—H6A1	120.0
C11A—C10A—H10A	119.6	C15A—N6A—H6A2	120.0
C9A—C10A—H10A	119.6	H6A1—N6A—H6A2	120.0
C11B—C10B—C9B	120.6 (5)	C15B—N6B—H6B1	120.0
C11B—C10B—H10B	119.7	C15B—N6B—H6B2	120.0
C9B—C10B—H10B	119.7	H6B1—N6B—H6B2	120.0
C10A—C11A—C12A	116.8 (4)	C17A—N7A—H7A3	120.0
C10A—C11A—H11A	121.6	C17A—N7A—H7A4	120.0
C12A—C11A—H11A	121.6	H7A3—N7A—H7A4	120.0
C10B—C11B—C12B	117.4 (4)	C17B—N7B—H7B3	120.0
C10B—C11B—H11B	121.3	C17B—N7B—H7B4	120.0
C12B—C11B—H11B	121.3	H7B3—N7B—H7B4	120.0
C11A—C12A—C8A	117.2 (4)	C19A—N8A—C16A	122.5 (4)
C11A—C12A—C13A	138.7 (4)	C19A—N8A—C18A	118.6 (4)
C8A—C12A—C13A	104.1 (4)	C16A—N8A—C18A	118.9 (4)
C11B—C12B—C8B	116.2 (4)	C19B—N8B—C16B	121.9 (5)
C11B—C12B—C13B	139.2 (4)	C19B—N8B—C18B	121.0 (5)
C8B—C12B—C13B	104.6 (4)	C16B—N8B—C18B	116.8 (4)
N3A—C13A—C12A	110.5 (3)	C19A—O2A—C20A	115.6 (4)
N3A—C13A—C14A	121.7 (4)	C19B—O2B—C20B	118.3 (5)
C6A—C1A—C2A—C3A	−0.4 (14)	N8A—C16A—C17A—N5A	−179.7 (4)
F1A—C1A—C2A—C3A	177.5 (8)	C15B—C16B—C17B—N7B	179.4 (5)
F1B—C1B—C2B—C3B	179.9 (6)	N8B—C16B—C17B—N7B	−3.5 (7)
C6B—C1B—C2B—C3B	0.3 (10)	C15B—C16B—C17B—N5B	0.5 (7)
C1A—C2A—C3A—C4A	−0.7 (14)	N8B—C16B—C17B—N5B	177.6 (4)
C1B—C2B—C3B—C4B	0.5 (10)	N2A—C8A—N1A—N3A	−176.5 (4)
C2A—C3A—C4A—C5A	1.4 (13)	C12A—C8A—N1A—N3A	2.2 (5)
C2B—C3B—C4B—C5B	−0.9 (10)	N2A—C8A—N1A—C7A	−2.2 (8)
C3A—C4A—C5A—C6A	−1.0 (11)	C12A—C8A—N1A—C7A	176.5 (5)
C3B—C4B—C5B—C6B	0.6 (8)	C6A—C7A—N1A—C8A	−88.4 (6)
C2A—C1A—C6A—C5A	0.7 (11)	C6A—C7A—N1A—N3A	85.5 (6)
F1A—C1A—C6A—C5A	−177.2 (6)	N2B—C8B—N1B—N3B	−177.3 (4)
C2A—C1A—C6A—C7A	−179.6 (7)	C12B—C8B—N1B—N3B	0.6 (5)
F1A—C1A—C6A—C7A	2.5 (9)	N2B—C8B—N1B—C7B	0.6 (8)
C4A—C5A—C6A—C1A	0.1 (10)	C12B—C8B—N1B—C7B	178.5 (4)
C4A—C5A—C6A—C7A	−179.6 (6)	C6B—C7B—N1B—N3B	−72.4 (5)
C4B—C5B—C6B—C1B	0.1 (7)	C6B—C7B—N1B—C8B	109.9 (5)
C4B—C5B—C6B—C7B	179.0 (5)	O1C—C1C—N1C—C2C	178.4 (6)
F1B—C1B—C6B—C5B	179.8 (5)	O1C—C1C—N1C—C3C	−3.6 (9)
C2B—C1B—C6B—C5B	−0.6 (8)	C10A—C9A—N2A—C8A	1.1 (8)
F1B—C1B—C6B—C7B	0.8 (7)	N1A—C8A—N2A—C9A	179.3 (5)
C2B—C1B—C6B—C7B	−179.5 (5)	C12A—C8A—N2A—C9A	0.8 (7)
C1A—C6A—C7A—N1A	166.2 (5)	C10B—C9B—N2B—C8B	−0.3 (8)
C5A—C6A—C7A—N1A	−14.1 (8)	N1B—C8B—N2B—C9B	178.2 (4)
C5B—C6B—C7B—N1B	16.5 (7)	C12B—C8B—N2B—C9B	0.7 (7)
C1B—C6B—C7B—N1B	−164.7 (4)	C12A—C13A—N3A—N1A	0.5 (5)
N2A—C9A—C10A—C11A	−1.7 (9)	C14A—C13A—N3A—N1A	177.7 (4)
N2B—C9B—C10B—C11B	0.0 (9)	C8A—N1A—N3A—C13A	−1.7 (5)
C9A—C10A—C11A—C12A	0.3 (8)	C7A—N1A—N3A—C13A	−176.5 (5)
C9B—C10B—C11B—C12B	−0.1 (8)	C12B—C13B—N3B—N1B	0.7 (5)
C10A—C11A—C12A—C8A	1.3 (7)	C14B—C13B—N3B—N1B	−178.4 (4)
C10A—C11A—C12A—C13A	−177.2 (5)	C8B—N1B—N3B—C13B	−0.8 (5)
N2A—C8A—C12A—C11A	−2.1 (7)	C7B—N1B—N3B—C13B	−178.9 (4)
N1A—C8A—C12A—C11A	179.2 (4)	N5A—C14A—N4A—C15A	−2.2 (6)
N2A—C8A—C12A—C13A	177.0 (5)	C13A—C14A—N4A—C15A	177.4 (4)
N1A—C8A—C12A—C13A	−1.7 (5)	N6A—C15A—N4A—C14A	179.5 (4)
C10B—C11B—C12B—C8B	0.4 (7)	C16A—C15A—N4A—C14A	−1.0 (6)
C10B—C11B—C12B—C13B	−177.3 (5)	N5B—C14B—N4B—C15B	2.5 (7)
N2B—C8B—C12B—C11B	−0.8 (7)	C13B—C14B—N4B—C15B	−178.0 (4)
N1B—C8B—C12B—C11B	−178.6 (4)	N6B—C15B—N4B—C14B	179.8 (4)
N2B—C8B—C12B—C13B	177.7 (4)	C16B—C15B—N4B—C14B	−1.4 (7)
N1B—C8B—C12B—C13B	−0.2 (5)	N4A—C14A—N5A—C17A	2.7 (6)
C11A—C12A—C13A—N3A	179.4 (5)	C13A—C14A—N5A—C17A	−176.9 (4)
C8A—C12A—C13A—N3A	0.7 (5)	N7A—C17A—N5A—C14A	−179.1 (4)
C11A—C12A—C13A—C14A	2.4 (9)	C16A—C17A—N5A—C14A	0.1 (6)
C8A—C12A—C13A—C14A	−176.3 (4)	N4B—C14B—N5B—C17B	−2.0 (7)
C11B—C12B—C13B—N3B	177.6 (5)	C13B—C14B—N5B—C17B	178.5 (4)
C8B—C12B—C13B—N3B	−0.3 (5)	N7B—C17B—N5B—C14B	−178.6 (4)
C11B—C12B—C13B—C14B	−3.5 (9)	C16B—C17B—N5B—C14B	0.4 (6)
C8B—C12B—C13B—C14B	178.7 (4)	O1A—C19A—N8A—C16A	174.9 (4)
N3A—C13A—C14A—N4A	179.6 (4)	O2A—C19A—N8A—C16A	−5.0 (6)
C12A—C13A—C14A—N4A	−3.7 (6)	O1A—C19A—N8A—C18A	−3.1 (6)
N3A—C13A—C14A—N5A	−0.8 (6)	O2A—C19A—N8A—C18A	177.0 (4)
C12A—C13A—C14A—N5A	175.9 (4)	C15A—C16A—N8A—C19A	83.9 (6)
N3B—C13B—C14B—N4B	−179.3 (4)	C17A—C16A—N8A—C19A	−99.3 (5)
C12B—C13B—C14B—N4B	1.8 (7)	C15A—C16A—N8A—C18A	−98.1 (5)
N3B—C13B—C14B—N5B	0.3 (6)	C17A—C16A—N8A—C18A	78.6 (5)
C12B—C13B—C14B—N5B	−178.6 (4)	O1B—C19B—N8B—C16B	−176.0 (5)
N6A—C15A—C16A—C17A	−177.2 (4)	O2B—C19B—N8B—C16B	4.5 (7)
N4A—C15A—C16A—C17A	3.4 (6)	O1B—C19B—N8B—C18B	−2.4 (8)
N6A—C15A—C16A—N8A	−0.5 (7)	O2B—C19B—N8B—C18B	178.2 (4)
N4A—C15A—C16A—N8A	−179.9 (4)	C15B—C16B—N8B—C19B	−95.0 (6)
N6B—C15B—C16B—C17B	178.8 (5)	C17B—C16B—N8B—C19B	88.0 (6)
N4B—C15B—C16B—C17B	0.1 (7)	C15B—C16B—N8B—C18B	91.1 (6)
N6B—C15B—C16B—N8B	1.7 (8)	C17B—C16B—N8B—C18B	−85.9 (5)
N4B—C15B—C16B—N8B	−177.0 (5)	O1A—C19A—O2A—C20A	−0.9 (6)
C15A—C16A—C17A—N7A	176.3 (4)	N8A—C19A—O2A—C20A	179.0 (4)
N8A—C16A—C17A—N7A	−0.6 (7)	O1B—C19B—O2B—C20B	4.6 (9)
C15A—C16A—C17A—N5A	−2.9 (7)	N8B—C19B—O2B—C20B	−175.9 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6B—H6B2···O1A^i	0.86	2.25	3.065 (5)	159
N6B—H6B1···O1A^ii	0.86	2.36	3.151 (5)	152
N6A—H6A2···O1B^iii	0.86	2.14	2.964 (5)	160
N6A—H6A1···O1C^iv	0.86	2.19	3.046 (6)	173
N7A—H7A3···N5B	0.86	2.26	3.098 (5)	166
N7A—H7A3···N3B	0.86	2.56	2.982 (5)	111
N7B—H7B3···N5A	0.86	2.16	3.017 (5)	175

Symmetry codes: (i) x, y+1, z; (ii) −x, −y+1, −z+2; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1.

(V)

Crystal data

C20H19FN8O2	Z = 4
Mr = 422.43	F(000) = 880
Triclinic, P1	Dx = 1.235 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 13.1749 (8) Å	Cell parameters from 9709 reflections
b = 13.7062 (9) Å	θ = 3.0–27.5°
c = 14.4719 (10) Å	µ = 0.09 mm^−1
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) Å^3

Data collection

Rigaku RAXIS-RAPID/ZJUG diffractometer	10187 independent reflections
Radiation source: rotating anode	3669 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
Detector resolution: 10.00 pixels mm^-1	θmax = 27.5°, θmin = 3.1°
ω scans	h = −16→17
Absorption correction: multi-scan Higashi, T. (1995)	k = −16→17
Tmin = 0.954, Tmax = 0.989	l = 0→18
10187 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.099	H-atom parameters constrained
wR(F^2) = 0.315	w = 1/[σ^2(Fo^2) + (0.1238P)^2 + 1.5P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max = 0.035
10187 reflections	Δρmax = 0.43 e Å^−3
564 parameters	Δρmin = −0.31 e Å^−3
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.0199 (5)	0.6299 (4)	0.7257 (6)	0.0826 (18)
C1B	0.0089 (4)	1.1058 (4)	0.2031 (5)	0.0670 (15)
C2A	−0.0472 (6)	0.6300 (5)	0.8200 (7)	0.115 (3)
H2A	−0.1226	0.6410	0.8291	0.138*
C2B	−0.0660 (5)	1.1086 (4)	0.2911 (5)	0.0825 (18)
H2B	−0.1400	1.1177	0.2945	0.099*
C3A	−0.0034 (8)	0.6143 (6)	0.8966 (7)	0.116 (3)
H3A	−0.0473	0.6141	0.9601	0.140*
C3B	−0.0294 (6)	1.0978 (4)	0.3736 (6)	0.089 (2)
H3B	−0.0784	1.0986	0.4347	0.107*
C4A	0.1059 (7)	0.5988 (5)	0.8814 (6)	0.106 (2)
H4A	0.1365	0.5859	0.9361	0.128*
C4B	0.0780 (6)	1.0859 (4)	0.3665 (5)	0.0829 (17)
H4B	0.1020	1.0791	0.4233	0.100*
C5A	0.1755 (5)	0.6011 (4)	0.7877 (5)	0.0829 (18)
H5A	0.2504	0.5918	0.7796	0.100*
C5B	0.1532 (5)	1.0835 (4)	0.2780 (4)	0.0668 (14)
H5B	0.2270	1.0751	0.2751	0.080*
C6A	0.1306 (4)	0.6173 (4)	0.7073 (4)	0.0644 (14)
C6B	0.1184 (4)	1.0936 (3)	0.1934 (4)	0.0556 (13)
C7A	0.1965 (4)	0.6200 (4)	0.6034 (4)	0.0672 (14)
H7A1	0.1971	0.5568	0.5869	0.081*
H7A2	0.1598	0.6822	0.5571	0.081*
C7B	0.1939 (4)	1.0932 (4)	0.0916 (4)	0.0648 (14)
H7B1	0.1985	1.0286	0.0751	0.078*
H7B2	0.1618	1.1541	0.0414	0.078*
C8A	0.3538 (4)	0.7086 (4)	0.5383 (4)	0.0528 (12)
C8B	0.3491 (4)	1.1827 (4)	0.0384 (4)	0.0539 (12)
C9A	0.3658 (5)	0.8723 (5)	0.4501 (5)	0.0813 (17)
H9A	0.3339	0.9425	0.4178	0.098*
C9B	0.3637 (5)	1.3437 (4)	−0.0535 (4)	0.0782 (17)
H9B	0.3340	1.4130	−0.0891	0.094*
C10A	0.4763 (5)	0.8455 (4)	0.4469 (5)	0.0814 (17)
H10A	0.5156	0.8971	0.4134	0.098*
C10B	0.4738 (5)	1.3166 (4)	−0.0496 (4)	0.0785 (17)
H10B	0.5144	1.3673	−0.0823	0.094*
C11A	0.5300 (4)	0.7432 (4)	0.4925 (4)	0.0651 (14)
H11A	0.6049	0.7240	0.4916	0.078*
C11B	0.5232 (4)	1.2165 (4)	0.0017 (4)	0.0690 (15)
H11B	0.5970	1.1972	0.0048	0.083*
C12A	0.4659 (4)	0.6703 (4)	0.5401 (4)	0.0537 (12)
C12B	0.4580 (4)	1.1455 (3)	0.0488 (3)	0.0499 (11)
C13A	0.4807 (4)	0.5603 (3)	0.5930 (4)	0.0538 (12)
C13B	0.4710 (4)	1.0351 (4)	0.1054 (4)	0.0528 (12)
C14A	0.5808 (4)	0.4780 (3)	0.6212 (4)	0.0515 (12)
C14B	0.5676 (4)	0.9579 (3)	0.1424 (3)	0.0480 (11)
C15A	0.7617 (4)	0.4385 (3)	0.6201 (4)	0.0549 (12)
C15B	0.7445 (4)	0.9236 (4)	0.1556 (4)	0.0566 (12)
C16A	0.7582 (4)	0.3361 (4)	0.6753 (4)	0.0577 (13)
C16B	0.7406 (3)	0.8194 (3)	0.2111 (4)	0.0514 (12)
C17A	0.6598 (4)	0.3078 (4)	0.7020 (4)	0.0535 (12)
C17B	0.6458 (4)	0.7884 (4)	0.2266 (4)	0.0515 (12)
C18A	0.9211 (4)	0.1895 (4)	0.6388 (5)	0.0826 (18)
H18A	0.9826	0.1405	0.6668	0.124*
H18B	0.9471	0.2345	0.5748	0.124*
H18C	0.8780	0.1498	0.6304	0.124*
C18B	0.9060 (4)	0.6678 (4)	0.1942 (5)	0.0795 (17)
H18D	0.9668	0.6253	0.2260	0.119*
H18E	0.9328	0.7069	0.1273	0.119*
H18F	0.8663	0.6216	0.1914	0.119*
C19A	0.8717 (5)	0.2299 (4)	0.7995 (5)	0.0747 (17)
C19B	0.8448 (4)	0.7326 (4)	0.3449 (4)	0.0583 (13)
C20A	0.8079 (6)	0.2710 (6)	0.9542 (5)	0.121 (3)
H20A	0.8121	0.1963	0.9856	0.181*
H20B	0.7449	0.3133	0.9896	0.181*
H20C	0.8731	0.2866	0.9559	0.181*
C20B	0.7813 (6)	0.8055 (6)	0.4813 (5)	0.106 (2)
H20D	0.7452	0.7535	0.5304	0.159*
H20E	0.7465	0.8746	0.4938	0.159*
H20F	0.8571	0.7854	0.4855	0.159*
F1A	−0.0244 (3)	0.6453 (3)	0.6465 (4)	0.1206 (14)
F1B	−0.0266 (3)	1.1173 (3)	0.1196 (3)	0.0931 (11)
N1A	0.3080 (3)	0.6240 (3)	0.5875 (3)	0.0606 (11)
N1B	0.3027 (3)	1.0976 (3)	0.0864 (3)	0.0591 (11)
N2A	0.3000 (4)	0.8062 (3)	0.4956 (3)	0.0691 (12)
N2B	0.2973 (4)	1.2790 (3)	−0.0106 (3)	0.0674 (12)
N3A	0.3858 (3)	0.5330 (3)	0.6210 (3)	0.0616 (11)
N3B	0.3774 (3)	1.0088 (3)	0.1278 (3)	0.0583 (11)
N4A	0.6716 (3)	0.5131 (3)	0.5897 (3)	0.0577 (11)
N4B	0.6562 (3)	0.9936 (3)	0.1195 (3)	0.0557 (10)
N5A	0.5679 (3)	0.3815 (3)	0.6745 (3)	0.0541 (10)
N5B	0.5570 (3)	0.8593 (3)	0.1912 (3)	0.0521 (10)
N6A	0.8555 (3)	0.4714 (3)	0.5887 (4)	0.0811 (15)
H6A1	0.8552	0.5357	0.5521	0.097*
H6A2	0.9154	0.4280	0.6054	0.097*
N6B	0.8339 (3)	0.9586 (3)	0.1352 (4)	0.0795 (15)
H6B1	0.8338	1.0234	0.1004	0.095*
H6B2	0.8917	0.9164	0.1569	0.095*
N7A	0.6501 (3)	0.2088 (3)	0.7541 (3)	0.0678 (12)
H7A3	0.5876	0.1942	0.7688	0.081*
H7A4	0.7062	0.1599	0.7729	0.081*
N7B	0.6367 (3)	0.6882 (3)	0.2768 (3)	0.0651 (12)
H7B3	0.5765	0.6716	0.2852	0.078*
H7B4	0.6910	0.6408	0.3005	0.078*
N8A	0.8537 (3)	0.2558 (3)	0.7062 (4)	0.0633 (12)
N8B	0.8326 (3)	0.7434 (3)	0.2519 (3)	0.0600 (11)
O1A	0.9433 (4)	0.1554 (3)	0.8321 (4)	0.1082 (16)
O1B	0.9136 (3)	0.6604 (3)	0.3857 (3)	0.0827 (12)
O2A	0.7984 (3)	0.2961 (3)	0.8526 (3)	0.0844 (12)
O2B	0.7738 (3)	0.8101 (3)	0.3826 (3)	0.0720 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.049 (4)	0.069 (3)	0.106 (5)	−0.007 (3)	−0.009 (4)	−0.007 (3)
C1B	0.049 (3)	0.054 (3)	0.089 (4)	−0.010 (2)	−0.023 (3)	−0.003 (3)
C2A	0.057 (4)	0.079 (4)	0.145 (8)	−0.009 (3)	0.033 (5)	−0.007 (5)
C2B	0.041 (3)	0.078 (4)	0.096 (5)	−0.011 (3)	0.004 (4)	−0.002 (3)
C3A	0.112 (8)	0.085 (5)	0.091 (6)	0.007 (5)	0.008 (5)	−0.004 (4)
C3B	0.076 (5)	0.068 (4)	0.089 (5)	−0.006 (3)	0.016 (4)	−0.018 (3)
C4A	0.118 (7)	0.076 (4)	0.089 (6)	0.001 (4)	−0.019 (5)	−0.003 (4)
C4B	0.080 (5)	0.080 (4)	0.083 (5)	−0.015 (3)	−0.015 (4)	−0.022 (3)
C5A	0.069 (4)	0.079 (4)	0.072 (4)	0.003 (3)	−0.008 (4)	−0.010 (3)
C5B	0.053 (3)	0.072 (3)	0.065 (4)	−0.010 (3)	−0.014 (3)	−0.010 (3)
C6A	0.041 (3)	0.053 (3)	0.075 (4)	−0.007 (2)	−0.005 (3)	0.000 (3)
C6B	0.032 (3)	0.051 (3)	0.069 (3)	−0.007 (2)	−0.007 (2)	−0.004 (2)
C7A	0.031 (3)	0.082 (3)	0.079 (4)	−0.011 (2)	−0.014 (3)	−0.011 (3)
C7B	0.042 (3)	0.074 (3)	0.072 (4)	−0.014 (2)	−0.021 (3)	−0.005 (3)
C8A	0.032 (3)	0.058 (3)	0.055 (3)	−0.002 (2)	−0.009 (2)	−0.008 (2)
C8B	0.040 (3)	0.061 (3)	0.055 (3)	−0.006 (2)	−0.011 (2)	−0.014 (2)
C9A	0.069 (4)	0.068 (3)	0.084 (4)	−0.008 (3)	−0.022 (3)	0.004 (3)
C9B	0.078 (4)	0.061 (3)	0.078 (4)	−0.003 (3)	−0.024 (3)	−0.004 (3)
C10A	0.070 (4)	0.067 (3)	0.092 (5)	−0.020 (3)	−0.016 (3)	0.000 (3)
C10B	0.066 (4)	0.062 (3)	0.090 (4)	−0.022 (3)	−0.016 (3)	0.007 (3)
C11A	0.050 (3)	0.065 (3)	0.068 (4)	−0.016 (3)	−0.010 (3)	−0.004 (3)
C11B	0.056 (3)	0.066 (3)	0.079 (4)	−0.015 (3)	−0.016 (3)	−0.012 (3)
C12A	0.042 (3)	0.056 (3)	0.056 (3)	0.000 (2)	−0.014 (2)	−0.015 (2)
C12B	0.040 (3)	0.060 (3)	0.045 (3)	−0.012 (2)	−0.008 (2)	−0.009 (2)
C13A	0.029 (3)	0.055 (3)	0.069 (3)	−0.003 (2)	−0.011 (2)	−0.013 (2)
C13B	0.033 (3)	0.055 (3)	0.065 (3)	−0.011 (2)	−0.011 (2)	−0.009 (2)
C14A	0.034 (3)	0.051 (3)	0.065 (3)	−0.006 (2)	−0.015 (2)	−0.010 (2)
C14B	0.036 (3)	0.052 (3)	0.050 (3)	−0.008 (2)	−0.013 (2)	−0.006 (2)
C15A	0.037 (3)	0.048 (3)	0.076 (4)	−0.012 (2)	−0.015 (2)	−0.009 (2)
C15B	0.036 (3)	0.056 (3)	0.076 (4)	−0.011 (2)	−0.020 (2)	−0.010 (3)
C16A	0.031 (3)	0.058 (3)	0.079 (4)	−0.009 (2)	−0.014 (2)	−0.012 (3)
C16B	0.029 (2)	0.051 (3)	0.070 (3)	−0.006 (2)	−0.017 (2)	−0.011 (2)
C17A	0.038 (3)	0.056 (3)	0.060 (3)	−0.008 (2)	−0.011 (2)	−0.010 (2)
C17B	0.032 (3)	0.060 (3)	0.058 (3)	−0.008 (2)	−0.011 (2)	−0.012 (2)
C18A	0.048 (3)	0.060 (3)	0.132 (6)	−0.001 (3)	−0.018 (3)	−0.030 (3)
C18B	0.044 (3)	0.069 (3)	0.127 (5)	−0.001 (3)	−0.020 (3)	−0.038 (3)
C19A	0.060 (4)	0.060 (3)	0.105 (5)	−0.026 (3)	−0.042 (4)	0.008 (3)
C19B	0.040 (3)	0.063 (3)	0.067 (4)	−0.021 (2)	−0.020 (3)	0.005 (3)
C20A	0.125 (7)	0.162 (7)	0.079 (5)	−0.059 (6)	−0.045 (5)	0.007 (5)
C20B	0.085 (5)	0.149 (6)	0.095 (5)	−0.031 (5)	−0.019 (4)	−0.045 (5)
F1A	0.052 (2)	0.142 (3)	0.166 (4)	−0.024 (2)	−0.024 (3)	−0.038 (3)
F1B	0.055 (2)	0.110 (3)	0.112 (3)	−0.0257 (18)	−0.036 (2)	−0.006 (2)
N1A	0.030 (2)	0.059 (2)	0.075 (3)	−0.0009 (18)	−0.013 (2)	−0.005 (2)
N1B	0.036 (2)	0.064 (2)	0.071 (3)	−0.0071 (19)	−0.021 (2)	−0.007 (2)
N2A	0.054 (3)	0.063 (3)	0.072 (3)	−0.002 (2)	−0.015 (2)	−0.005 (2)
N2B	0.053 (3)	0.062 (3)	0.069 (3)	−0.001 (2)	−0.015 (2)	−0.007 (2)
N3A	0.040 (2)	0.061 (2)	0.074 (3)	−0.0067 (19)	−0.014 (2)	−0.012 (2)
N3B	0.038 (2)	0.057 (2)	0.071 (3)	−0.0061 (19)	−0.020 (2)	−0.005 (2)
N4A	0.037 (2)	0.053 (2)	0.076 (3)	−0.0072 (18)	−0.018 (2)	−0.007 (2)
N4B	0.039 (2)	0.050 (2)	0.074 (3)	−0.0112 (18)	−0.016 (2)	−0.0075 (19)
N5A	0.031 (2)	0.056 (2)	0.067 (3)	−0.0077 (17)	−0.0120 (19)	−0.008 (2)
N5B	0.038 (2)	0.056 (2)	0.061 (3)	−0.0123 (18)	−0.0162 (19)	−0.0078 (19)
N6A	0.042 (3)	0.057 (2)	0.131 (4)	−0.013 (2)	−0.033 (3)	0.005 (3)
N6B	0.046 (3)	0.060 (2)	0.129 (4)	−0.023 (2)	−0.036 (3)	0.005 (3)
N7A	0.038 (2)	0.056 (2)	0.099 (3)	−0.0123 (19)	−0.020 (2)	−0.003 (2)
N7B	0.045 (2)	0.056 (2)	0.090 (3)	−0.0172 (19)	−0.026 (2)	0.000 (2)
N8A	0.038 (2)	0.050 (2)	0.091 (3)	−0.0068 (18)	−0.018 (2)	−0.006 (2)
N8B	0.036 (2)	0.052 (2)	0.085 (3)	−0.0070 (18)	−0.017 (2)	−0.011 (2)
O1A	0.078 (3)	0.079 (3)	0.161 (5)	−0.005 (2)	−0.075 (3)	0.005 (3)
O1B	0.055 (2)	0.080 (2)	0.098 (3)	−0.0128 (19)	−0.036 (2)	0.007 (2)
O2A	0.072 (3)	0.095 (3)	0.086 (3)	−0.011 (2)	−0.037 (2)	−0.015 (2)
O2B	0.054 (2)	0.088 (3)	0.072 (3)	−0.009 (2)	−0.0181 (19)	−0.025 (2)

Geometric parameters (Å, º)

C1A—F1A	1.359 (7)	C13A—C14A	1.484 (6)
C1A—C6A	1.367 (7)	C13B—N3B	1.317 (6)
C1A—C2A	1.391 (9)	C13B—C14B	1.469 (6)
C1B—F1B	1.364 (6)	C14A—N5A	1.323 (6)
C1B—C2B	1.366 (8)	C14A—N4A	1.335 (6)
C1B—C6B	1.367 (7)	C14B—N4B	1.322 (5)
C2A—C3A	1.320 (11)	C14B—N5B	1.328 (5)
C2A—H2A	0.9300	C15A—N6A	1.355 (6)
C2B—C3B	1.361 (9)	C15A—N4A	1.360 (5)
C2B—H2B	0.9300	C15A—C16A	1.369 (6)
C3A—C4A	1.345 (10)	C15B—N6B	1.333 (6)
C3A—H3A	0.9300	C15B—N4B	1.353 (5)
C3B—C4B	1.347 (8)	C15B—C16B	1.391 (6)
C3B—H3B	0.9300	C16A—C17A	1.383 (6)
C4A—C5A	1.393 (9)	C16A—N8A	1.443 (6)
C4A—H4A	0.9300	C16B—C17B	1.382 (6)
C4B—C5B	1.373 (8)	C16B—N8B	1.441 (5)
C4B—H4B	0.9300	C17A—N7A	1.338 (6)
C5A—C6A	1.376 (8)	C17A—N5A	1.361 (5)
C5A—H5A	0.9300	C17B—N7B	1.346 (6)
C5B—C6B	1.379 (7)	C17B—N5B	1.357 (5)
C5B—H5B	0.9300	C18A—N8A	1.458 (6)
C6A—C7A	1.494 (7)	C18A—H18A	0.9600
C6B—C7B	1.517 (7)	C18A—H18B	0.9600
C7A—N1A	1.435 (6)	C18A—H18C	0.9600
C7A—H7A1	0.9700	C18B—N8B	1.470 (6)
C7A—H7A2	0.9700	C18B—H18D	0.9600
C7B—N1B	1.434 (6)	C18B—H18E	0.9600
C7B—H7B1	0.9700	C18B—H18F	0.9600
C7B—H7B2	0.9700	C19A—O1A	1.207 (6)
C8A—N2A	1.322 (5)	C19A—N8A	1.346 (7)
C8A—N1A	1.365 (6)	C19A—O2A	1.344 (7)
C8A—C12A	1.400 (6)	C19B—O1B	1.215 (5)
C8B—N2B	1.331 (6)	C19B—O2B	1.318 (6)
C8B—N1B	1.374 (6)	C19B—N8B	1.355 (6)
C8B—C12B	1.390 (6)	C20A—O2A	1.426 (7)
C9A—N2A	1.336 (7)	C20A—H20A	0.9600
C9A—C10A	1.369 (8)	C20A—H20B	0.9600
C9A—H9A	0.9300	C20A—H20C	0.9600
C9B—N2B	1.325 (7)	C20B—O2B	1.439 (7)
C9B—C10B	1.387 (8)	C20B—H20D	0.9600
C9B—H9B	0.9300	C20B—H20E	0.9600
C10A—C11A	1.378 (7)	C20B—H20F	0.9600
C10A—H10A	0.9300	N1A—N3A	1.373 (5)
C10B—C11B	1.365 (7)	N1B—N3B	1.369 (5)
C10B—H10B	0.9300	N6A—H6A1	0.8600
C11A—C12A	1.391 (7)	N6A—H6A2	0.8600
C11A—H11A	0.9300	N6B—H6B1	0.8600
C11B—C12B	1.382 (6)	N6B—H6B2	0.8600
C11B—H11B	0.9300	N7A—H7A3	0.8600
C12A—C13A	1.418 (6)	N7A—H7A4	0.8600
C12B—C13B	1.436 (6)	N7B—H7B3	0.8600
C13A—N3A	1.332 (6)	N7B—H7B4	0.8600
F1A—C1A—C6A	117.1 (6)	N4A—C14A—C13A	114.5 (4)
F1A—C1A—C2A	120.2 (7)	N4B—C14B—N5B	127.8 (4)
C6A—C1A—C2A	122.7 (7)	N4B—C14B—C13B	116.1 (4)
F1B—C1B—C2B	119.0 (5)	N5B—C14B—C13B	116.0 (4)
F1B—C1B—C6B	117.5 (5)	N6A—C15A—N4A	115.5 (4)
C2B—C1B—C6B	123.5 (6)	N6A—C15A—C16A	122.5 (4)
C3A—C2A—C1A	119.7 (8)	N4A—C15A—C16A	122.0 (4)
C3A—C2A—H2A	120.1	N6B—C15B—N4B	117.3 (4)
C1A—C2A—H2A	120.1	N6B—C15B—C16B	122.3 (4)
C3B—C2B—C1B	118.2 (6)	N4B—C15B—C16B	120.4 (4)
C3B—C2B—H2B	120.9	C15A—C16A—C17A	119.1 (4)
C1B—C2B—H2B	120.9	C15A—C16A—N8A	122.4 (4)
C2A—C3A—C4A	118.9 (8)	C17A—C16A—N8A	118.5 (4)
C2A—C3A—H3A	120.5	C17B—C16B—C15B	118.7 (4)
C4A—C3A—H3A	120.5	C17B—C16B—N8B	119.6 (4)
C4B—C3B—C2B	119.8 (6)	C15B—C16B—N8B	121.8 (4)
C4B—C3B—H3B	120.1	N7A—C17A—N5A	117.1 (4)
C2B—C3B—H3B	120.1	N7A—C17A—C16A	122.8 (4)
C3A—C4A—C5A	123.2 (8)	N5A—C17A—C16A	120.1 (4)
C3A—C4A—H4A	118.4	N7B—C17B—N5B	117.0 (4)
C5A—C4A—H4A	118.4	N7B—C17B—C16B	122.3 (4)
C3B—C4B—C5B	122.0 (6)	N5B—C17B—C16B	120.7 (4)
C3B—C4B—H4B	119.0	N8A—C18A—H18A	109.5
C5B—C4B—H4B	119.0	N8A—C18A—H18B	109.5
C6A—C5A—C4A	118.4 (6)	H18A—C18A—H18B	109.5
C6A—C5A—H5A	120.8	N8A—C18A—H18C	109.5
C4A—C5A—H5A	120.8	H18A—C18A—H18C	109.5
C4B—C5B—C6B	119.4 (5)	H18B—C18A—H18C	109.5
C4B—C5B—H5B	120.3	N8B—C18B—H18D	109.5
C6B—C5B—H5B	120.3	N8B—C18B—H18E	109.5
C1A—C6A—C5A	117.1 (6)	H18D—C18B—H18E	109.5
C1A—C6A—C7A	119.3 (6)	N8B—C18B—H18F	109.5
C5A—C6A—C7A	123.6 (5)	H18D—C18B—H18F	109.5
C1B—C6B—C5B	117.1 (5)	H18E—C18B—H18F	109.5
C1B—C6B—C7B	118.9 (5)	O1A—C19A—N8A	124.4 (7)
C5B—C6B—C7B	124.0 (4)	O1A—C19A—O2A	124.1 (6)
N1A—C7A—C6A	115.4 (4)	N8A—C19A—O2A	111.5 (5)
N1A—C7A—H7A1	108.4	O1B—C19B—O2B	126.0 (5)
C6A—C7A—H7A1	108.4	O1B—C19B—N8B	122.9 (5)
N1A—C7A—H7A2	108.4	O2B—C19B—N8B	111.0 (4)
C6A—C7A—H7A2	108.4	O2A—C20A—H20A	109.5
H7A1—C7A—H7A2	107.5	O2A—C20A—H20B	109.5
N1B—C7B—C6B	113.8 (4)	H20A—C20A—H20B	109.5
N1B—C7B—H7B1	108.8	O2A—C20A—H20C	109.5
C6B—C7B—H7B1	108.8	H20A—C20A—H20C	109.5
N1B—C7B—H7B2	108.8	H20B—C20A—H20C	109.5
C6B—C7B—H7B2	108.8	O2B—C20B—H20D	109.5
H7B1—C7B—H7B2	107.7	O2B—C20B—H20E	109.5
N2A—C8A—N1A	124.9 (4)	H20D—C20B—H20E	109.5
N2A—C8A—C12A	128.2 (5)	O2B—C20B—H20F	109.5
N1A—C8A—C12A	106.9 (4)	H20D—C20B—H20F	109.5
N2B—C8B—N1B	124.6 (4)	H20E—C20B—H20F	109.5
N2B—C8B—C12B	128.9 (5)	C8A—N1A—N3A	110.9 (4)
N1B—C8B—C12B	106.4 (4)	C8A—N1A—C7A	129.0 (4)
N2A—C9A—C10A	125.5 (5)	N3A—N1A—C7A	120.1 (4)
N2A—C9A—H9A	117.3	N3B—N1B—C8B	110.9 (4)
C10A—C9A—H9A	117.3	N3B—N1B—C7B	121.0 (4)
N2B—C9B—C10B	125.5 (5)	C8B—N1B—C7B	128.0 (4)
N2B—C9B—H9B	117.2	C8A—N2A—C9A	112.2 (4)
C10B—C9B—H9B	117.2	C8B—N2B—C9B	111.5 (4)
C9A—C10A—C11A	121.0 (5)	C13A—N3A—N1A	106.5 (4)
C9A—C10A—H10A	119.5	C13B—N3B—N1B	107.2 (4)
C11A—C10A—H10A	119.5	C14A—N4A—C15A	114.0 (4)
C11B—C10B—C9B	120.7 (5)	C14B—N4B—C15B	116.3 (4)
C11B—C10B—H10B	119.6	C14A—N5A—C17A	115.7 (4)
C9B—C10B—H10B	119.6	C14B—N5B—C17B	116.0 (4)
C10A—C11A—C12A	116.1 (5)	C15A—N6A—H6A1	120.0
C10A—C11A—H11A	122.0	C15A—N6A—H6A2	120.0
C12A—C11A—H11A	122.0	H6A1—N6A—H6A2	120.0
C10B—C11B—C12B	116.6 (5)	C15B—N6B—H6B1	120.0
C10B—C11B—H11B	121.7	C15B—N6B—H6B2	120.0
C12B—C11B—H11B	121.7	H6B1—N6B—H6B2	120.0
C11A—C12A—C8A	117.0 (4)	C17A—N7A—H7A3	120.0
C11A—C12A—C13A	137.9 (4)	C17A—N7A—H7A4	120.0
C8A—C12A—C13A	105.1 (4)	H7A3—N7A—H7A4	120.0
C11B—C12B—C8B	116.9 (4)	C17B—N7B—H7B3	120.0
C11B—C12B—C13B	137.7 (5)	C17B—N7B—H7B4	120.0
C8B—C12B—C13B	105.4 (4)	H7B3—N7B—H7B4	120.0
N3A—C13A—C12A	110.6 (4)	C19A—N8A—C16A	122.2 (5)
N3A—C13A—C14A	119.0 (4)	C19A—N8A—C18A	119.7 (5)
C12A—C13A—C14A	130.4 (4)	C16A—N8A—C18A	117.3 (5)
N3B—C13B—C12B	110.1 (4)	C19B—N8B—C16B	122.0 (4)
N3B—C13B—C14B	120.8 (4)	C19B—N8B—C18B	120.3 (4)
C12B—C13B—C14B	129.1 (4)	C16B—N8B—C18B	117.2 (4)
N5A—C14A—N4A	129.1 (4)	C19A—O2A—C20A	115.2 (5)
N5A—C14A—C13A	116.4 (4)	C19B—O2B—C20B	114.9 (5)
F1A—C1A—C2A—C3A	179.6 (6)	C15A—C16A—C17A—N5A	−0.7 (8)
C6A—C1A—C2A—C3A	−2.0 (10)	N8A—C16A—C17A—N5A	179.8 (4)
F1B—C1B—C2B—C3B	−179.5 (5)	C15B—C16B—C17B—N7B	177.9 (5)
C6B—C1B—C2B—C3B	−0.7 (8)	N8B—C16B—C17B—N7B	−1.7 (7)
C1A—C2A—C3A—C4A	0.1 (12)	C15B—C16B—C17B—N5B	−2.1 (7)
C1B—C2B—C3B—C4B	0.8 (9)	N8B—C16B—C17B—N5B	178.2 (4)
C2A—C3A—C4A—C5A	1.7 (12)	N2A—C8A—N1A—N3A	178.4 (5)
C2B—C3B—C4B—C5B	−0.5 (9)	C12A—C8A—N1A—N3A	0.2 (5)
C3A—C4A—C5A—C6A	−1.7 (10)	N2A—C8A—N1A—C7A	0.5 (8)
C3B—C4B—C5B—C6B	0.1 (8)	C12A—C8A—N1A—C7A	−177.7 (5)
F1A—C1A—C6A—C5A	−179.6 (5)	C6A—C7A—N1A—C8A	−105.3 (6)
C2A—C1A—C6A—C5A	1.9 (8)	C6A—C7A—N1A—N3A	77.0 (6)
F1A—C1A—C6A—C7A	−0.5 (8)	N2B—C8B—N1B—N3B	178.6 (4)
C2A—C1A—C6A—C7A	−178.9 (5)	C12B—C8B—N1B—N3B	0.9 (5)
C4A—C5A—C6A—C1A	−0.1 (8)	N2B—C8B—N1B—C7B	1.9 (8)
C4A—C5A—C6A—C7A	−179.2 (5)	C12B—C8B—N1B—C7B	−175.8 (4)
F1B—C1B—C6B—C5B	179.2 (4)	C6B—C7B—N1B—N3B	76.7 (6)
C2B—C1B—C6B—C5B	0.3 (7)	C6B—C7B—N1B—C8B	−107.0 (6)
F1B—C1B—C6B—C7B	−0.3 (7)	N1A—C8A—N2A—C9A	−177.9 (5)
C2B—C1B—C6B—C7B	−179.1 (5)	C12A—C8A—N2A—C9A	−0.1 (8)
C4B—C5B—C6B—C1B	0.0 (7)	C10A—C9A—N2A—C8A	−0.5 (9)
C4B—C5B—C6B—C7B	179.4 (5)	N1B—C8B—N2B—C9B	−177.0 (5)
C1A—C6A—C7A—N1A	170.1 (5)	C12B—C8B—N2B—C9B	0.1 (8)
C5A—C6A—C7A—N1A	−10.8 (7)	C10B—C9B—N2B—C8B	0.4 (8)
C1B—C6B—C7B—N1B	170.4 (4)	C12A—C13A—N3A—N1A	−0.1 (6)
C5B—C6B—C7B—N1B	−9.0 (7)	C14A—C13A—N3A—N1A	178.5 (4)
N2A—C9A—C10A—C11A	0.2 (10)	C8A—N1A—N3A—C13A	0.0 (6)
N2B—C9B—C10B—C11B	−0.3 (10)	C7A—N1A—N3A—C13A	178.1 (4)
C9A—C10A—C11A—C12A	0.7 (8)	C12B—C13B—N3B—N1B	1.0 (5)
C9B—C10B—C11B—C12B	−0.2 (8)	C14B—C13B—N3B—N1B	177.7 (4)
C10A—C11A—C12A—C8A	−1.1 (7)	C8B—N1B—N3B—C13B	−1.2 (5)
C10A—C11A—C12A—C13A	177.8 (6)	C7B—N1B—N3B—C13B	175.7 (4)
N2A—C8A—C12A—C11A	0.9 (8)	N5A—C14A—N4A—C15A	−2.1 (8)
N1A—C8A—C12A—C11A	179.0 (4)	C13A—C14A—N4A—C15A	177.0 (4)
N2A—C8A—C12A—C13A	−178.4 (5)	N6A—C15A—N4A—C14A	179.6 (4)
N1A—C8A—C12A—C13A	−0.2 (5)	C16A—C15A—N4A—C14A	2.0 (7)
C10B—C11B—C12B—C8B	0.6 (7)	N5B—C14B—N4B—C15B	−4.8 (7)
C10B—C11B—C12B—C13B	176.6 (6)	C13B—C14B—N4B—C15B	178.4 (4)
N2B—C8B—C12B—C11B	−0.6 (8)	N6B—C15B—N4B—C14B	−178.6 (4)
N1B—C8B—C12B—C11B	177.0 (4)	C16B—C15B—N4B—C14B	1.8 (7)
N2B—C8B—C12B—C13B	−177.8 (5)	N4A—C14A—N5A—C17A	0.7 (8)
N1B—C8B—C12B—C13B	−0.2 (5)	C13A—C14A—N5A—C17A	−178.3 (4)
C11A—C12A—C13A—N3A	−178.8 (6)	N7A—C17A—N5A—C14A	−178.6 (4)
C8A—C12A—C13A—N3A	0.2 (6)	C16A—C17A—N5A—C14A	0.8 (7)
C11A—C12A—C13A—C14A	2.7 (10)	N4B—C14B—N5B—C17B	4.1 (7)
C8A—C12A—C13A—C14A	−178.3 (5)	C13B—C14B—N5B—C17B	−179.1 (4)
C11B—C12B—C13B—N3B	−176.8 (6)	N7B—C17B—N5B—C14B	179.6 (4)
C8B—C12B—C13B—N3B	−0.5 (5)	C16B—C17B—N5B—C14B	−0.3 (7)
C11B—C12B—C13B—C14B	6.9 (10)	O1A—C19A—N8A—C16A	171.3 (5)
C8B—C12B—C13B—C14B	−176.8 (5)	O2A—C19A—N8A—C16A	−7.5 (6)
N3A—C13A—C14A—N5A	−0.8 (7)	O1A—C19A—N8A—C18A	2.1 (8)
C12A—C13A—C14A—N5A	177.6 (5)	O2A—C19A—N8A—C18A	−176.6 (4)
N3A—C13A—C14A—N4A	180.0 (4)	C15A—C16A—N8A—C19A	100.4 (6)
C12A—C13A—C14A—N4A	−1.6 (8)	C17A—C16A—N8A—C19A	−80.1 (6)
N3B—C13B—C14B—N4B	−177.1 (4)	C15A—C16A—N8A—C18A	−90.2 (6)
C12B—C13B—C14B—N4B	−1.2 (8)	C17A—C16A—N8A—C18A	89.2 (6)
N3B—C13B—C14B—N5B	5.7 (7)	O1B—C19B—N8B—C16B	170.4 (4)
C12B—C13B—C14B—N5B	−178.4 (4)	O2B—C19B—N8B—C16B	−10.1 (6)
N6A—C15A—C16A—C17A	−178.2 (5)	O1B—C19B—N8B—C18B	−1.6 (7)
N4A—C15A—C16A—C17A	−0.7 (8)	O2B—C19B—N8B—C18B	177.9 (4)
N6A—C15A—C16A—N8A	1.3 (8)	C17B—C16B—N8B—C19B	−89.8 (6)
N4A—C15A—C16A—N8A	178.8 (5)	C15B—C16B—N8B—C19B	90.6 (6)
N6B—C15B—C16B—C17B	−178.3 (5)	C17B—C16B—N8B—C18B	82.4 (6)
N4B—C15B—C16B—C17B	1.4 (7)	C15B—C16B—N8B—C18B	−97.2 (6)
N6B—C15B—C16B—N8B	1.4 (8)	O1A—C19A—O2A—C20A	−1.8 (8)
N4B—C15B—C16B—N8B	−179.0 (4)	N8A—C19A—O2A—C20A	176.9 (5)
C15A—C16A—C17A—N7A	178.6 (5)	O1B—C19B—O2B—C20B	−0.1 (7)
N8A—C16A—C17A—N7A	−0.9 (8)	N8B—C19B—O2B—C20B	−179.5 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N6A—H6A2···O1B^i	0.86	2.20	3.041 (5)	167
N6B—H6B2···O1A^i	0.86	2.10	2.928 (6)	162
N7A—H7A3···N5B^ii	0.86	2.12	2.975 (5)	174
N7B—H7B3···N5A^ii	0.86	2.11	2.966 (5)	172
N6A—H6A1···O1B	0.86	2.51	3.280 (6)	149

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.