3,4-Bis­(4-fluoro­phen­yl)-1,2,5-oxadiazole 2-oxide

The title compound, C₁₄H₈F₂N₂O₂, also known as di(4-F-phen­yl)furazan N-oxide, was found as a side product in the synthesis of isoxazole derivatives. The are two molecules in the asymmetric unit. The bond length of the dipolar N-O unit is 1.107 (7) Å. X-ray analysis confirmed the compound to have the desired structure

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.006 Å
• Disorder in main residue
• R factor = 0.074
• wR factor = 0.232
• Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of Tmax/Tmin expected RT(exp) is > 1.10
            Absorption corrections should be applied.
            Tmin and Tmax expected:      0.802     0.900
            RT(exp) =      1.123
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.118
PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.12
PLAT057_ALERT_3_C Correction for Absorption Required   RT(exp) ...       1.16
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              C14 H8 F2 N2 O2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   6 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius 1989); cell refinement: CAD-4 Software; data reduction: Corinc (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2005); software used to prepare material for publication: SHELXL97.

(II)

Crystal data

C14H8F2N2O2	F(000) = 1120
Mr = 274.22	Dx = 1.493 Mg m^−3
Monoclinic, P21/c	Melting point: 118 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54178 Å
a = 17.797 (2) Å	Cell parameters from 25 reflections
b = 10.3032 (7) Å	θ = 30–46°
c = 14.2799 (14) Å	µ = 1.05 mm^−1
β = 111.251 (10)°	T = 193 K
V = 2440.4 (4) Å^3	Block, light yellow
Z = 8	0.40 × 0.20 × 0.10 mm

Data collection

CAD-4 Enraf–Nonius diffractometer	Rint = 0.118
Radiation source: rotating anode	θmax = 70.2°, θmin = 2.7°
Graphite monochromator	h = 0→21
ω/2θ scans	k = 0→12
4791 measured reflections	l = −17→16
4637 independent reflections	3 standard reflections every 60 min
3152 reflections with I > 2σ(I)	intensity decay: 5%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.232	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.1284P)^2 + 1.3775P] where P = (Fo^2 + 2Fc^2)/3
4637 reflections	(Δ/σ)max < 0.001
371 parameters	Δρmax = 0.56 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

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

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1A	0.3715 (2)	−0.0034 (4)	0.3800 (3)	0.0488 (9)
C2A	0.4054 (2)	−0.1132 (4)	0.4400 (3)	0.0466 (8)
N3A	0.4299 (2)	−0.0863 (3)	0.5379 (3)	0.0627 (9)
O4A	0.41084 (18)	0.0421 (3)	0.5436 (2)	0.0685 (8)
N5A	0.3749 (2)	0.0923 (3)	0.4434 (3)	0.0582 (9)
O6A	0.3545 (2)	0.2052 (3)	0.4356 (3)	0.0814 (10)
C7A	0.33572 (19)	0.0140 (3)	0.2703 (3)	0.0449 (8)
C8A	0.2865 (2)	−0.0838 (4)	0.2101 (3)	0.0467 (8)
H8A	0.2785	−0.1659	0.2490	0.056*
C9A	0.2533 (2)	−0.0688 (4)	0.1074 (3)	0.0578 (10)
H9A	0.2178	−0.1452	0.0638	0.069*
C10A	0.2703 (3)	0.0433 (5)	0.0664 (3)	0.0673 (12)
C11A	0.3181 (3)	0.1400 (4)	0.1228 (4)	0.0678 (12)
H11A	0.3348	0.2250	0.0879	0.081*
C12A	0.3510 (2)	0.1256 (4)	0.2262 (3)	0.0570 (10)
H12A	0.3882	0.1987	0.2618	0.068*
F13A	0.23764 (18)	0.0544 (4)	−0.0348 (2)	0.1011 (11)
C14A	0.41664 (19)	−0.2435 (4)	0.4064 (3)	0.0455 (8)
C15A	0.4439 (2)	−0.2586 (4)	0.3270 (3)	0.0499 (9)
H15A	0.4580	−0.1795	0.2978	0.060*
C16A	0.4540 (2)	−0.3814 (4)	0.2941 (3)	0.0541 (9)
H16A	0.4743	−0.3916	0.2331	0.065*
C17A	0.4362 (2)	−0.4854 (4)	0.3416 (4)	0.0603 (11)
C18A	0.4093 (2)	−0.4745 (4)	0.4194 (3)	0.0596 (11)
H18A	0.3842	−0.5400	0.4500	0.072*
F19A	0.44707 (18)	−0.6060 (2)	0.3106 (3)	0.0900 (10)
C19A	0.3989 (2)	−0.3520 (4)	0.4525 (3)	0.0507 (9)
H19A	0.3812	−0.3527	0.5140	0.061*
C1B	0.02924 (19)	0.1681 (3)	0.1272 (3)	0.0443 (8)
C2B	0.0377 (2)	0.0502 (3)	0.1811 (3)	0.0453 (8)
N3B	−0.0196 (2)	−0.0311 (4)	0.1299 (3)	0.0657 (10)
O4B	−0.06769 (18)	0.0318 (3)	0.0429 (3)	0.0781 (10)
N5B	−0.0346 (2)	0.1573 (3)	0.0439 (3)	0.0602 (9)
O6B	−0.0733 (3)	0.2175 (4)	−0.0265 (3)	0.0606 (16)	0.608 (8)
O6C	−0.0421 (5)	−0.1317 (8)	0.1277 (7)	0.082 (3)	0.392 (8)
C7B	0.07859 (19)	0.2868 (3)	0.1506 (2)	0.0396 (7)
C8B	0.1613 (2)	0.2795 (3)	0.2040 (3)	0.0437 (8)
H8B	0.1875	0.1955	0.2260	0.052*
C9B	0.2070 (2)	0.3915 (4)	0.2311 (3)	0.0495 (8)
H9B	0.2670	0.3871	0.2821	0.059*
C10B	0.1691 (2)	0.5089 (4)	0.2053 (3)	0.0510 (9)
C11B	0.0882 (2)	0.5195 (4)	0.1497 (3)	0.0525 (9)
H11B	0.0529	0.6032	0.1218	0.063*
C12B	0.0425 (2)	0.4076 (3)	0.1227 (3)	0.0456 (8)
H12B	−0.0188	0.4191	0.0818	0.055*
F13B	0.21327 (16)	0.6179 (2)	0.2348 (2)	0.0708 (7)
C14B	0.0965 (2)	0.0107 (3)	0.2788 (3)	0.0446 (8)
C15B	0.1203 (2)	0.0977 (4)	0.3599 (3)	0.0497 (8)
H15B	0.0896	0.1901	0.3487	0.060*
C16B	0.1739 (2)	0.0580 (4)	0.4523 (3)	0.0573 (10)
H16B	0.2005	0.1043	0.5206	0.069*
C17B	0.2035 (2)	−0.0681 (5)	0.4616 (3)	0.0603 (11)
C18B	0.1812 (2)	−0.1553 (4)	0.3844 (3)	0.0588 (10)
H18B	0.2132	−0.2478	0.4000	0.071*
F19B	0.25720 (16)	−0.1048 (3)	0.55232 (19)	0.0808 (8)
C19B	0.1269 (2)	−0.1147 (4)	0.2921 (3)	0.0524 (9)
H19B	0.1086	−0.1737	0.2333	0.063*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.0439 (18)	0.054 (2)	0.056 (2)	−0.0159 (15)	0.0273 (16)	−0.0213 (17)
C2A	0.0426 (18)	0.056 (2)	0.0429 (19)	−0.0089 (15)	0.0176 (15)	−0.0093 (16)
N3A	0.064 (2)	0.064 (2)	0.066 (2)	−0.0069 (16)	0.0308 (17)	−0.0164 (17)
O4A	0.0753 (19)	0.079 (2)	0.0535 (17)	−0.0157 (16)	0.0262 (15)	−0.0217 (15)
N5A	0.063 (2)	0.0474 (18)	0.073 (2)	−0.0087 (15)	0.0349 (17)	−0.0135 (16)
O6A	0.102 (3)	0.0564 (19)	0.098 (3)	−0.0039 (17)	0.050 (2)	−0.0155 (17)
C7A	0.0409 (17)	0.0401 (17)	0.060 (2)	−0.0033 (13)	0.0254 (16)	−0.0040 (15)
C8A	0.0445 (18)	0.0485 (19)	0.048 (2)	−0.0033 (15)	0.0181 (15)	−0.0047 (15)
C9A	0.051 (2)	0.072 (3)	0.050 (2)	0.0039 (18)	0.0177 (17)	−0.0052 (19)
C10A	0.054 (2)	0.101 (4)	0.052 (2)	0.021 (2)	0.0260 (19)	0.021 (2)
C11A	0.061 (3)	0.062 (3)	0.090 (3)	0.008 (2)	0.040 (2)	0.021 (2)
C12A	0.052 (2)	0.050 (2)	0.078 (3)	0.0003 (16)	0.033 (2)	0.0063 (19)
F13A	0.0823 (19)	0.165 (3)	0.0575 (16)	0.021 (2)	0.0274 (14)	0.0316 (18)
C14A	0.0334 (16)	0.056 (2)	0.0413 (18)	−0.0055 (14)	0.0072 (14)	−0.0077 (15)
C15A	0.0484 (19)	0.055 (2)	0.048 (2)	−0.0083 (16)	0.0198 (16)	−0.0035 (17)
C16A	0.048 (2)	0.054 (2)	0.061 (2)	−0.0078 (16)	0.0202 (17)	−0.0134 (18)
C17A	0.0432 (19)	0.052 (2)	0.080 (3)	−0.0052 (16)	0.0150 (19)	−0.014 (2)
C18A	0.044 (2)	0.053 (2)	0.075 (3)	−0.0058 (16)	0.0133 (19)	0.005 (2)
F19A	0.0883 (19)	0.0488 (14)	0.135 (3)	−0.0082 (13)	0.0431 (19)	−0.0220 (15)
C19A	0.0414 (18)	0.062 (2)	0.044 (2)	−0.0050 (16)	0.0098 (15)	0.0060 (17)
C1B	0.0373 (16)	0.0495 (19)	0.0452 (19)	−0.0020 (14)	0.0140 (14)	−0.0081 (15)
C2B	0.0447 (18)	0.0456 (19)	0.0455 (19)	−0.0068 (14)	0.0159 (15)	−0.0132 (15)
N3B	0.0544 (19)	0.064 (2)	0.071 (2)	−0.0117 (17)	0.0138 (17)	−0.0156 (18)
O4B	0.0551 (17)	0.081 (2)	0.077 (2)	−0.0126 (15)	−0.0011 (15)	−0.0321 (18)
N5B	0.0508 (18)	0.067 (2)	0.050 (2)	0.0024 (16)	0.0034 (15)	−0.0133 (17)
O6B	0.063 (3)	0.056 (3)	0.051 (3)	−0.002 (2)	0.005 (2)	0.005 (2)
O6C	0.089 (6)	0.061 (5)	0.100 (7)	−0.052 (4)	0.040 (5)	−0.020 (4)
C7B	0.0426 (17)	0.0430 (17)	0.0341 (16)	0.0019 (13)	0.0151 (13)	−0.0022 (13)
C8B	0.0420 (17)	0.0434 (18)	0.0449 (19)	0.0001 (14)	0.0148 (14)	0.0052 (15)
C9B	0.0461 (19)	0.052 (2)	0.048 (2)	−0.0032 (16)	0.0152 (16)	0.0018 (16)
C10B	0.064 (2)	0.0441 (19)	0.049 (2)	−0.0114 (16)	0.0252 (18)	−0.0078 (16)
C11B	0.062 (2)	0.0433 (19)	0.054 (2)	0.0072 (16)	0.0232 (18)	0.0011 (16)
C12B	0.0459 (18)	0.0489 (19)	0.0420 (18)	0.0066 (15)	0.0161 (15)	−0.0012 (15)
F13B	0.0781 (16)	0.0487 (13)	0.0861 (18)	−0.0190 (11)	0.0303 (14)	−0.0120 (12)
C14B	0.0451 (18)	0.0458 (18)	0.047 (2)	−0.0077 (14)	0.0214 (15)	−0.0010 (15)
C15B	0.057 (2)	0.049 (2)	0.046 (2)	−0.0111 (16)	0.0221 (16)	−0.0034 (16)
C16B	0.059 (2)	0.062 (2)	0.050 (2)	−0.0162 (19)	0.0198 (18)	0.0008 (18)
C17B	0.050 (2)	0.080 (3)	0.051 (2)	−0.0037 (19)	0.0187 (18)	0.015 (2)
C18B	0.060 (2)	0.065 (2)	0.058 (2)	0.0072 (19)	0.0285 (19)	0.009 (2)
F19B	0.0732 (16)	0.105 (2)	0.0568 (15)	0.0048 (15)	0.0149 (13)	0.0200 (14)
C19B	0.058 (2)	0.051 (2)	0.054 (2)	−0.0012 (17)	0.0272 (18)	0.0007 (17)

Geometric parameters (Å, º)

C1A—N5A	1.325 (5)	C1B—C2B	1.417 (5)
C1A—C2A	1.416 (5)	C1B—C7B	1.472 (5)
C1A—C7A	1.472 (5)	C2B—N3B	1.317 (5)
C2A—N3A	1.333 (5)	C2B—C14B	1.466 (5)
C2A—C14A	1.463 (5)	N3B—O6C	1.107 (7)
N3A—O4A	1.375 (5)	N3B—O4B	1.388 (5)
O4A—N5A	1.436 (5)	O4B—N5B	1.419 (5)
N5A—O6A	1.212 (4)	N5B—O6B	1.169 (5)
C7A—C12A	1.384 (5)	C7B—C12B	1.390 (5)
C7A—C8A	1.406 (5)	C7B—C8B	1.393 (5)
C8A—C9A	1.377 (5)	C8B—C9B	1.383 (5)
C8A—H8A	1.0502	C8B—H8B	0.9790
C9A—C10A	1.377 (6)	C9B—C10B	1.368 (5)
C9A—H9A	1.0589	C9B—H9B	1.0535
C10A—F13A	1.354 (5)	C10B—F13B	1.348 (4)
C10A—C11A	1.367 (7)	C10B—C11B	1.373 (5)
C11A—C12A	1.385 (6)	C11B—C12B	1.383 (5)
C11A—H11A	1.0996	C11B—H11B	1.0567
C12A—H12A	1.0106	C12B—H12B	1.0416
C14A—C19A	1.390 (5)	C14B—C19B	1.386 (5)
C14A—C15A	1.395 (5)	C14B—C15B	1.403 (5)
C15A—C16A	1.384 (5)	C15B—C16B	1.381 (5)
C15A—H15A	0.9881	C15B—H15B	1.0808
C16A—C17A	1.365 (6)	C16B—C17B	1.390 (6)
C16A—H16A	1.0623	C16B—H16B	1.0331
C17A—F19A	1.356 (5)	C17B—F19B	1.356 (5)
C17A—C18A	1.364 (7)	C17B—C18B	1.364 (6)
C18A—C19A	1.384 (6)	C18B—C19B	1.388 (6)
C18A—H18A	0.9934	C18B—H18B	1.0911
C19A—H19A	1.0361	C19B—H19B	0.9915
C1B—N5B	1.319 (5)
N5A—C1A—C2A	106.0 (3)	N5B—C1B—C7B	121.5 (3)
N5A—C1A—C7A	122.1 (4)	C2B—C1B—C7B	130.8 (3)
C2A—C1A—C7A	131.8 (3)	N3B—C2B—C1B	109.6 (3)
N3A—C2A—C1A	112.0 (3)	N3B—C2B—C14B	119.6 (4)
N3A—C2A—C14A	120.2 (3)	C1B—C2B—C14B	130.8 (3)
C1A—C2A—C14A	127.8 (3)	O6C—N3B—C2B	144.1 (6)
C2A—N3A—O4A	105.6 (3)	O6C—N3B—O4B	108.2 (6)
N3A—O4A—N5A	108.5 (3)	C2B—N3B—O4B	107.6 (3)
O6A—N5A—C1A	135.5 (4)	N3B—O4B—N5B	107.3 (3)
O6A—N5A—O4A	116.6 (3)	O6B—N5B—C1B	141.0 (4)
C1A—N5A—O4A	107.9 (3)	O6B—N5B—O4B	111.2 (3)
C12A—C7A—C8A	119.9 (4)	C1B—N5B—O4B	107.7 (3)
C12A—C7A—C1A	120.3 (3)	C12B—C7B—C8B	119.4 (3)
C8A—C7A—C1A	119.7 (3)	C12B—C7B—C1B	120.2 (3)
C9A—C8A—C7A	120.1 (4)	C8B—C7B—C1B	120.3 (3)
C9A—C8A—H8A	124.5	C9B—C8B—C7B	120.3 (3)
C7A—C8A—H8A	115.4	C9B—C8B—H8B	119.0
C10A—C9A—C8A	118.1 (4)	C7B—C8B—H8B	120.6
C10A—C9A—H9A	123.3	C10B—C9B—C8B	118.7 (3)
C8A—C9A—H9A	118.5	C10B—C9B—H9B	120.1
F13A—C10A—C11A	120.1 (5)	C8B—C9B—H9B	120.2
F13A—C10A—C9A	116.7 (5)	F13B—C10B—C9B	118.6 (3)
C11A—C10A—C9A	123.2 (4)	F13B—C10B—C11B	119.0 (3)
C10A—C11A—C12A	118.8 (4)	C9B—C10B—C11B	122.5 (3)
C10A—C11A—H11A	121.8	C10B—C11B—C12B	118.8 (3)
C12A—C11A—H11A	119.3	C10B—C11B—H11B	129.7
C7A—C12A—C11A	119.9 (4)	C12B—C11B—H11B	111.4
C7A—C12A—H12A	126.3	C11B—C12B—C7B	120.2 (3)
C11A—C12A—H12A	113.7	C11B—C12B—H12B	116.9
C19A—C14A—C15A	120.0 (4)	C7B—C12B—H12B	122.9
C19A—C14A—C2A	120.1 (3)	C19B—C14B—C15B	119.7 (3)
C15A—C14A—C2A	119.9 (3)	C19B—C14B—C2B	119.9 (3)
C16A—C15A—C14A	120.3 (4)	C15B—C14B—C2B	120.4 (3)
C16A—C15A—H15A	121.8	C16B—C15B—C14B	119.8 (4)
C14A—C15A—H15A	117.8	C16B—C15B—H15B	122.6
C17A—C16A—C15A	117.8 (4)	C14B—C15B—H15B	117.1
C17A—C16A—H16A	122.6	C15B—C16B—C17B	118.3 (4)
C15A—C16A—H16A	119.5	C15B—C16B—H16B	133.4
F19A—C17A—C18A	118.4 (4)	C17B—C16B—H16B	108.3
F19A—C17A—C16A	118.1 (4)	F19B—C17B—C18B	119.1 (4)
C18A—C17A—C16A	123.6 (4)	F19B—C17B—C16B	117.6 (4)
C17A—C18A—C19A	118.9 (4)	C18B—C17B—C16B	123.4 (4)
C17A—C18A—H18A	130.4	C17B—C18B—C19B	117.8 (4)
C19A—C18A—H18A	109.4	C17B—C18B—H18B	115.7
C18A—C19A—C14A	119.4 (4)	C19B—C18B—H18B	126.1
C18A—C19A—H19A	113.8	C14B—C19B—C18B	121.0 (4)
C14A—C19A—H19A	126.7	C14B—C19B—H19B	117.6
N5B—C1B—C2B	107.8 (3)	C18B—C19B—H19B	121.4
N5A—C1A—C2A—N3A	−0.5 (4)	N5B—C1B—C2B—C14B	−178.4 (4)
C7A—C1A—C2A—N3A	−178.9 (3)	C7B—C1B—C2B—C14B	2.4 (6)
N5A—C1A—C2A—C14A	−179.3 (3)	C1B—C2B—N3B—O6C	174.0 (10)
C7A—C1A—C2A—C14A	2.3 (6)	C14B—C2B—N3B—O6C	−6.5 (12)
C1A—C2A—N3A—O4A	1.1 (4)	C1B—C2B—N3B—O4B	−1.3 (4)
C14A—C2A—N3A—O4A	180.0 (3)	C14B—C2B—N3B—O4B	178.2 (3)
C2A—N3A—O4A—N5A	−1.2 (4)	O6C—N3B—O4B—N5B	−176.1 (6)
C2A—C1A—N5A—O6A	−179.0 (4)	C2B—N3B—O4B—N5B	1.0 (4)
C7A—C1A—N5A—O6A	−0.5 (7)	C2B—C1B—N5B—O6B	176.6 (6)
C2A—C1A—N5A—O4A	−0.2 (4)	C7B—C1B—N5B—O6B	−4.2 (9)
C7A—C1A—N5A—O4A	178.3 (3)	C2B—C1B—N5B—O4B	−0.4 (4)
N3A—O4A—N5A—O6A	180.0 (3)	C7B—C1B—N5B—O4B	178.9 (3)
N3A—O4A—N5A—C1A	0.9 (4)	N3B—O4B—N5B—O6B	−178.3 (4)
N5A—C1A—C7A—C12A	42.1 (5)	N3B—O4B—N5B—C1B	−0.4 (4)
C2A—C1A—C7A—C12A	−139.8 (4)	N5B—C1B—C7B—C12B	35.1 (5)
N5A—C1A—C7A—C8A	−138.5 (4)	C2B—C1B—C7B—C12B	−145.8 (4)
C2A—C1A—C7A—C8A	39.6 (5)	N5B—C1B—C7B—C8B	−147.3 (4)
C12A—C7A—C8A—C9A	0.0 (5)	C2B—C1B—C7B—C8B	31.8 (5)
C1A—C7A—C8A—C9A	−179.4 (3)	C12B—C7B—C8B—C9B	1.4 (5)
C7A—C8A—C9A—C10A	0.3 (5)	C1B—C7B—C8B—C9B	−176.2 (3)
C8A—C9A—C10A—F13A	179.3 (3)	C7B—C8B—C9B—C10B	0.7 (5)
C8A—C9A—C10A—C11A	−0.2 (6)	C8B—C9B—C10B—F13B	177.7 (3)
F13A—C10A—C11A—C12A	−179.7 (4)	C8B—C9B—C10B—C11B	−3.1 (6)
C9A—C10A—C11A—C12A	−0.3 (6)	F13B—C10B—C11B—C12B	−177.7 (3)
C8A—C7A—C12A—C11A	−0.5 (5)	C9B—C10B—C11B—C12B	3.1 (6)
C1A—C7A—C12A—C11A	178.9 (3)	C10B—C11B—C12B—C7B	−0.8 (6)
C10A—C11A—C12A—C7A	0.6 (6)	C8B—C7B—C12B—C11B	−1.3 (5)
N3A—C2A—C14A—C19A	44.1 (5)	C1B—C7B—C12B—C11B	176.3 (3)
C1A—C2A—C14A—C19A	−137.2 (4)	N3B—C2B—C14B—C19B	40.0 (5)
N3A—C2A—C14A—C15A	−136.9 (4)	C1B—C2B—C14B—C19B	−140.7 (4)
C1A—C2A—C14A—C15A	41.8 (5)	N3B—C2B—C14B—C15B	−137.8 (4)
C19A—C14A—C15A—C16A	−0.5 (5)	C1B—C2B—C14B—C15B	41.5 (5)
C2A—C14A—C15A—C16A	−179.5 (3)	C19B—C14B—C15B—C16B	0.2 (5)
C14A—C15A—C16A—C17A	0.3 (5)	C2B—C14B—C15B—C16B	178.0 (3)
C15A—C16A—C17A—F19A	−179.2 (3)	C14B—C15B—C16B—C17B	0.7 (5)
C15A—C16A—C17A—C18A	−0.2 (6)	C15B—C16B—C17B—F19B	178.7 (3)
F19A—C17A—C18A—C19A	179.2 (3)	C15B—C16B—C17B—C18B	−1.2 (6)
C16A—C17A—C18A—C19A	0.3 (6)	F19B—C17B—C18B—C19B	−179.3 (3)
C17A—C18A—C19A—C14A	−0.5 (5)	C16B—C17B—C18B—C19B	0.7 (6)
C15A—C14A—C19A—C18A	0.6 (5)	C15B—C14B—C19B—C18B	−0.7 (5)
C2A—C14A—C19A—C18A	179.6 (3)	C2B—C14B—C19B—C18B	−178.5 (3)
N5B—C1B—C2B—N3B	1.0 (4)	C17B—C18B—C19B—C14B	0.3 (6)
C7B—C1B—C2B—N3B	−178.2 (4)