4,4-Difluoro-1,3,5,7,8-penta­methyl-2,6-dibutyl-3a,4a-diaza-4-bora-s-indacene

There are two mol­ecules in the asymmetric unit of the title compound, C₂₂H₃₃BF₂N₂, also known as Pyrromethene 580. The dihedral angle between the least squares planes of the bora-s-indacene rings of the two molecules (A and B) is 80.2 (6)°. The F atoms extend an average distance of 1.127 (6) Å (in A) and 1.230 (2) Å (in B) from the mean plane deviation of this ring [0.024 (4) Å in A and 0.018 (2) Å in B]. The dihedral angle between the mean planes of the bora-s-indacene rings of each mol­ecule is 80.2 (6)°.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.067
• wR factor = 0.322
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.80

Author Response: Data collected on an old AFC6S diffractometer.

PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.76

Author Response: data collected on an old AFC6S diffractometer.

PLAT412_ALERT_2_A Short Intra XH3 .. XHn     H44    ..  H48     ..       1.66 Ang.

Author Response: data collected on an old AFC6S diffractometer.

Alert level B
PLAT026_ALERT_3_B Ratio Observed / Unique Reflections too Low ....         32 Perc.
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.66 Ratio
PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         12
PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H5     ..  H15     ..       1.74 Ang.

Author Response: data collected on an old AFC6S diffractometer.

PLAT412_ALERT_2_B Short Intra XH3 .. XHn     H41    ..  H45     ..       1.72 Ang.

Author Response: data collected on an old AFC6S diffractometer.

Alert level C
RFACR01_ALERT_3_C  The value of the weighted R factor is > 0.25
            Weighted R factor given   0.322
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT084_ALERT_2_C High R2 Value ..................................       0.32
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.53 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C21B   -   C22B    ..       5.51 su
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C21B   -   C22B   ...       1.39 Ang.

Alert level G
REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values
           From the CIF: _diffrn_reflns_theta_max           26.30
           From the CIF: _reflns_number_total               6939
           From the CIF: _diffrn_reflns_limit_ max hkl   10.   15.   23.
           From the CIF: _diffrn_reflns_limit_ min hkl  -10.    0.  -25.
           TEST1: Expected hkl limits for theta max
           Calculated maximum hkl   10.   18.   24.
           Calculated minimum hkl  -10.  -18.  -24.

   3 ALERT level A = In general: serious problem
   5 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

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

---

Computing details

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: CrystalStructure (Rigaku/MSC, 2005); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.

4,4-Difluoro-1,3,5,7,8-pentamethyl-2,6-dibutyl-3a,4a-diaza-4-bora-s-indacene

Crystal data

C22H33BF2N2	Z = 4
Mr = 374.31	F(000) = 808
Triclinic, P1	Dx = 1.168 Mg m^−3
a = 8.182 (4) Å	Mo Kα radiation, λ = 0.71069 Å
b = 14.7272 (15) Å	Cell parameters from 25 reflections
c = 19.380 (5) Å	θ = 6.2–7.7°
α = 111.227 (17)°	µ = 0.08 mm^−1
β = 99.452 (18)°	T = 296 K
γ = 79.47 (2)°	Block, orange
V = 2127.9 (11) Å^3	0.50 × 0.40 × 0.30 mm

Data collection

Rigaku AFC-6S diffractometer	2231 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.096
Graphite monochromator	θmax = 26.3°, θmin = 1.5°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→15
Tmin = 0.961, Tmax = 0.977	l = −25→23
7323 measured reflections	3 standard reflections every 150 reflections
6939 independent reflections	intensity decay: 0.2%

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)] = 0.067	H-atom parameters constrained
wR(F^2) = 0.322	w = 1/[σ^2(Fo^2) + (0.1652P)^2 + 0.0805P] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max < 0.001
6939 reflections	Δρmax = 0.27 e Å^−3
489 parameters	Δρmin = −0.30 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (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
F1A	0.5916 (5)	1.1992 (3)	0.1839 (2)	0.0790 (12)
F1B	0.2918 (5)	0.8005 (3)	0.2592 (2)	0.0890 (13)
F2B	0.1871 (5)	0.8376 (3)	0.3686 (2)	0.0829 (13)
F2A	0.8688 (5)	1.1524 (3)	0.2053 (2)	0.0772 (12)
N1A	0.7624 (6)	1.1675 (4)	0.0860 (3)	0.0538 (14)
N1B	0.3551 (6)	0.9479 (4)	0.3584 (3)	0.0548 (14)
N2A	0.7006 (6)	1.0318 (4)	0.1202 (3)	0.0512 (13)
N2B	0.4819 (7)	0.7846 (4)	0.3632 (3)	0.0572 (14)
C1B	0.2449 (8)	1.0226 (6)	0.3472 (4)	0.0619 (19)
C1A	0.7900 (8)	1.2556 (6)	0.0893 (4)	0.0630 (19)
C2B	0.3181 (9)	1.1104 (5)	0.3773 (4)	0.0628 (19)
C2A	0.8296 (8)	1.2511 (6)	0.0203 (4)	0.070 (2)
C3B	0.4755 (9)	1.0883 (5)	0.4086 (3)	0.0578 (18)
C3A	0.8260 (7)	1.1553 (6)	−0.0269 (4)	0.0606 (19)
C4B	0.5010 (8)	0.9870 (5)	0.3970 (3)	0.0498 (16)
C4A	0.7818 (7)	1.1019 (5)	0.0136 (4)	0.0538 (17)
C5A	0.7561 (7)	1.0031 (5)	−0.0059 (3)	0.0507 (17)
C5B	0.6384 (7)	0.9222 (5)	0.4158 (3)	0.0502 (16)
C6B	0.6297 (8)	0.8239 (5)	0.3984 (3)	0.0532 (16)
C6A	0.7144 (7)	0.9687 (5)	0.0466 (4)	0.0551 (17)
C7B	0.7488 (8)	0.7460 (5)	0.4114 (4)	0.0613 (19)
C7A	0.6800 (7)	0.8766 (5)	0.0424 (4)	0.0595 (18)
C8A	0.6481 (8)	0.8826 (6)	0.1121 (4)	0.0623 (19)
C8B	0.6681 (10)	0.6623 (6)	0.3833 (4)	0.074 (2)
C9A	0.6626 (7)	0.9796 (6)	0.1590 (4)	0.0576 (18)
C9B	0.5064 (10)	0.6885 (5)	0.3551 (4)	0.0648 (19)
C10A	0.6343 (8)	1.0249 (6)	0.2396 (4)	0.075 (2)
H1	0.7385	1.0196	0.2698	0.090*
H2	0.5568	0.9911	0.2501	0.090*
H3	0.5894	1.0929	0.2505	0.090*
C10B	0.3709 (11)	0.6248 (6)	0.3195 (5)	0.102 (3)
H34	0.3062	0.6261	0.3570	0.123*
H35	0.4201	0.5586	0.2952	0.123*
H36	0.2998	0.6489	0.2836	0.123*
C11B	0.0742 (9)	1.0096 (6)	0.3085 (4)	0.085 (2)
H37	0.0761	0.9949	0.2562	0.102*
H38	−0.0003	1.0690	0.3280	0.102*
H39	0.0363	0.9565	0.3164	0.102*
C11A	0.7765 (10)	1.3440 (6)	0.1594 (4)	0.090 (2)
H10	0.6642	1.3775	0.1596	0.108*
H11	0.8523	1.3877	0.1612	0.108*
H12	0.8044	1.3233	0.2019	0.108*
C12B	0.5916 (10)	1.1634 (5)	0.4483 (4)	0.080 (2)
H40	0.6563	1.1688	0.4133	0.096*
H41	0.6651	1.1436	0.4859	0.096*
H42	0.5277	1.2259	0.4713	0.096*
C12A	0.8634 (9)	1.1202 (6)	−0.1058 (4)	0.079 (2)
H13	0.9809	1.0981	−0.1081	0.095*
H14	0.8318	1.1730	−0.1253	0.095*
H15	0.8016	1.0668	−0.1349	0.095*
C13B	0.7973 (8)	0.9630 (5)	0.4549 (4)	0.070 (2)
H43	0.8689	0.9577	0.4187	0.084*
H44	0.8529	0.9265	0.4862	0.084*
H45	0.7715	1.0308	0.4847	0.084*
C13A	0.7693 (9)	0.9341 (5)	−0.0840 (3)	0.076 (2)
H4	0.8819	0.9014	−0.0887	0.092*
H5	0.7402	0.9703	−0.1177	0.092*
H6	0.6944	0.8862	−0.0958	0.092*
C14B	0.9241 (9)	0.7488 (6)	0.4467 (5)	0.091 (3)
H46	0.9979	0.7342	0.4092	0.109*
H47	0.9526	0.7010	0.4711	0.109*
H48	0.9353	0.8131	0.4825	0.109*
C14A	0.6773 (9)	0.7812 (5)	−0.0239 (4)	0.085 (2)
H7	0.5667	0.7783	−0.0497	0.101*
H8	0.7091	0.7263	−0.0067	0.101*
H9	0.7545	0.7788	−0.0571	0.101*
C15B	0.2312 (10)	1.2076 (6)	0.3725 (4)	0.080 (2)
H55	0.2623	1.2592	0.4184	0.096*
H56	0.1115	1.2077	0.3687	0.096*
C15A	0.8715 (9)	1.3345 (6)	0.0023 (5)	0.091 (3)
H22	0.9667	1.3106	−0.0265	0.109*
H23	0.9051	1.3848	0.0485	0.109*
C16B	0.2692 (9)	1.2322 (5)	0.3081 (4)	0.068 (2)
H57	0.3895	1.2272	0.3095	0.081*
H58	0.2297	1.1837	0.2619	0.081*
C16A	0.7310 (9)	1.3813 (6)	−0.0409 (5)	0.084 (2)
H24	0.7005	1.3317	−0.0881	0.101*
H25	0.6341	1.4030	−0.0132	0.101*
C17B	0.1920 (10)	1.3328 (5)	0.3075 (4)	0.082 (2)
H59	0.0716	1.3375	0.3054	0.099*
H60	0.2303	1.3813	0.3539	0.099*
C17A	0.7724 (11)	1.4671 (7)	−0.0559 (6)	0.106 (3)
H26	0.7885	1.5200	−0.0087	0.127*
H27	0.8776	1.4478	−0.0775	0.127*
C18B	0.2307 (11)	1.3578 (6)	0.2448 (5)	0.104 (3)
H49	0.3316	1.3877	0.2591	0.125*
H50	0.1402	1.4028	0.2326	0.125*
H51	0.2452	1.2990	0.2023	0.125*
C18A	0.6478 (13)	1.5045 (7)	−0.1049 (6)	0.128 (4)
H19	0.6718	1.4710	−0.1555	0.154*
H20	0.6500	1.5737	−0.0921	0.154*
H21	0.5391	1.4936	−0.0996	0.154*
C19A	0.6144 (9)	0.8047 (6)	0.1372 (5)	0.080 (2)
H28	0.5560	0.7576	0.0960	0.096*
H29	0.5413	0.8341	0.1765	0.096*
C19B	0.7397 (11)	0.5590 (5)	0.3807 (5)	0.091 (3)
H61	0.6936	0.5127	0.3348	0.109*
H62	0.8597	0.5507	0.3796	0.109*
C20A	0.7740 (9)	0.7497 (6)	0.1663 (5)	0.083 (2)
H30	0.8454	0.7192	0.1264	0.099*
H31	0.8339	0.7974	0.2063	0.099*
C20B	0.7048 (13)	0.5347 (6)	0.4450 (5)	0.107 (3)
H63	0.5846	0.5412	0.4448	0.128*
H64	0.7468	0.5830	0.4907	0.128*
C21A	0.7451 (11)	0.6732 (7)	0.1939 (5)	0.104 (3)
H32	0.6878	0.6245	0.1537	0.124*
H33	0.6724	0.7032	0.2333	0.124*
C21B	0.7808 (15)	0.4312 (7)	0.4463 (7)	0.133 (4)
H65	0.9013	0.4248	0.4475	0.160*
H66	0.7575	0.4252	0.4919	0.160*
C22A	0.9017 (12)	0.6228 (7)	0.2230 (6)	0.128 (4)
H16	0.9452	0.5672	0.1831	0.154*
H17	0.8776	0.6011	0.2609	0.154*
H18	0.9829	0.6678	0.2437	0.154*
C22B	0.7218 (17)	0.3545 (9)	0.3863 (9)	0.184 (6)
H52	0.6256	0.3366	0.3983	0.220*
H53	0.8076	0.2989	0.3755	0.220*
H54	0.6912	0.3748	0.3436	0.220*
B1B	0.3227 (10)	0.8424 (6)	0.3360 (4)	0.062 (2)
B1A	0.7311 (9)	1.1393 (6)	0.1506 (4)	0.055 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1A	0.084 (3)	0.077 (3)	0.074 (3)	0.014 (2)	0.031 (2)	0.025 (2)
F1B	0.102 (3)	0.094 (3)	0.066 (3)	−0.022 (2)	−0.015 (2)	0.027 (2)
F2B	0.064 (2)	0.100 (3)	0.105 (3)	−0.024 (2)	0.016 (2)	0.050 (3)
F2A	0.080 (3)	0.093 (3)	0.061 (2)	−0.020 (2)	−0.019 (2)	0.036 (2)
N1A	0.045 (3)	0.062 (4)	0.056 (4)	−0.005 (3)	0.001 (2)	0.026 (3)
N1B	0.053 (3)	0.066 (4)	0.051 (3)	−0.008 (3)	0.008 (3)	0.027 (3)
N2A	0.048 (3)	0.059 (4)	0.047 (3)	0.002 (3)	0.010 (2)	0.021 (3)
N2B	0.063 (4)	0.054 (4)	0.058 (3)	−0.010 (3)	0.012 (3)	0.019 (3)
C1B	0.055 (4)	0.087 (6)	0.056 (4)	0.002 (4)	0.008 (3)	0.044 (4)
C1A	0.052 (4)	0.073 (6)	0.066 (5)	−0.009 (4)	−0.008 (3)	0.033 (4)
C2B	0.074 (5)	0.068 (5)	0.056 (4)	0.012 (4)	0.025 (4)	0.036 (4)
C2A	0.048 (4)	0.098 (7)	0.075 (5)	−0.014 (4)	0.002 (4)	0.043 (5)
C3B	0.078 (5)	0.054 (5)	0.045 (4)	−0.011 (4)	0.016 (4)	0.017 (3)
C3A	0.046 (4)	0.093 (6)	0.054 (5)	−0.001 (4)	0.005 (3)	0.042 (5)
C4B	0.050 (4)	0.062 (5)	0.039 (4)	−0.007 (4)	0.007 (3)	0.019 (3)
C4A	0.042 (4)	0.061 (5)	0.057 (5)	−0.001 (3)	0.000 (3)	0.024 (4)
C5A	0.035 (3)	0.074 (5)	0.043 (4)	0.005 (3)	0.002 (3)	0.027 (4)
C5B	0.048 (4)	0.070 (5)	0.039 (4)	−0.011 (3)	0.013 (3)	0.021 (3)
C6B	0.057 (4)	0.056 (5)	0.052 (4)	−0.006 (4)	0.014 (3)	0.022 (4)
C6A	0.040 (4)	0.064 (5)	0.056 (5)	0.007 (3)	0.004 (3)	0.020 (4)
C7B	0.063 (5)	0.070 (5)	0.062 (4)	0.004 (4)	0.021 (4)	0.035 (4)
C7A	0.044 (4)	0.063 (5)	0.068 (5)	−0.003 (3)	−0.001 (3)	0.023 (4)
C8A	0.045 (4)	0.074 (6)	0.076 (5)	−0.004 (4)	0.005 (3)	0.037 (5)
C8B	0.088 (6)	0.067 (6)	0.074 (5)	0.003 (5)	0.031 (4)	0.029 (4)
C9A	0.037 (4)	0.092 (6)	0.058 (4)	−0.004 (4)	0.005 (3)	0.044 (5)
C9B	0.082 (6)	0.052 (5)	0.064 (5)	−0.017 (4)	0.012 (4)	0.019 (4)
C10A	0.063 (5)	0.104 (6)	0.065 (5)	0.005 (4)	0.020 (4)	0.038 (4)
C10B	0.130 (8)	0.081 (6)	0.096 (7)	−0.041 (6)	−0.007 (6)	0.026 (5)
C11B	0.074 (5)	0.099 (6)	0.085 (6)	0.009 (4)	0.010 (4)	0.044 (5)
C11A	0.100 (6)	0.081 (6)	0.083 (6)	−0.012 (5)	−0.006 (5)	0.028 (5)
C12B	0.104 (6)	0.066 (5)	0.075 (5)	−0.012 (5)	0.013 (4)	0.028 (4)
C12A	0.065 (5)	0.111 (6)	0.078 (5)	0.001 (4)	0.014 (4)	0.054 (5)
C13B	0.055 (4)	0.073 (5)	0.089 (5)	−0.014 (4)	0.002 (4)	0.036 (4)
C13A	0.078 (5)	0.093 (6)	0.050 (5)	−0.003 (4)	0.005 (4)	0.020 (4)
C14B	0.066 (5)	0.105 (7)	0.121 (7)	0.009 (4)	0.016 (5)	0.069 (6)
C14A	0.073 (5)	0.081 (6)	0.094 (6)	−0.009 (4)	−0.006 (4)	0.031 (5)
C15B	0.088 (5)	0.086 (6)	0.074 (5)	0.014 (4)	0.027 (4)	0.041 (5)
C15A	0.070 (5)	0.114 (7)	0.116 (7)	−0.035 (5)	−0.007 (5)	0.069 (6)
C16B	0.078 (5)	0.063 (5)	0.070 (5)	0.010 (4)	0.020 (4)	0.036 (4)
C16A	0.078 (5)	0.086 (6)	0.111 (6)	−0.019 (4)	−0.003 (5)	0.061 (5)
C17B	0.093 (6)	0.078 (6)	0.090 (6)	0.014 (4)	0.023 (4)	0.051 (5)
C17A	0.107 (7)	0.103 (7)	0.138 (8)	−0.022 (5)	−0.012 (6)	0.084 (6)
C18B	0.102 (6)	0.099 (7)	0.129 (8)	0.006 (5)	0.026 (6)	0.064 (6)
C18A	0.158 (10)	0.117 (8)	0.128 (9)	−0.024 (7)	0.005 (7)	0.064 (7)
C19A	0.062 (5)	0.094 (6)	0.101 (6)	−0.007 (4)	0.012 (4)	0.054 (5)
C19B	0.113 (7)	0.066 (6)	0.107 (7)	0.012 (5)	0.033 (5)	0.047 (5)
C20A	0.080 (5)	0.086 (6)	0.102 (6)	−0.002 (4)	0.022 (5)	0.055 (5)
C20B	0.150 (8)	0.069 (6)	0.102 (7)	0.013 (5)	0.029 (6)	0.038 (5)
C21A	0.107 (7)	0.104 (7)	0.120 (8)	−0.009 (6)	0.021 (6)	0.060 (6)
C21B	0.160 (10)	0.083 (8)	0.149 (10)	−0.010 (7)	0.007 (8)	0.038 (7)
C22A	0.127 (9)	0.141 (9)	0.145 (9)	0.030 (7)	0.041 (7)	0.094 (8)
C22B	0.186 (13)	0.127 (11)	0.261 (18)	−0.023 (10)	0.067 (12)	0.075 (12)
B1B	0.062 (5)	0.078 (6)	0.049 (5)	−0.014 (5)	−0.002 (4)	0.029 (5)
B1A	0.049 (5)	0.068 (6)	0.048 (5)	0.010 (4)	0.011 (4)	0.028 (4)

Geometric parameters (Å, º)

F1A—B1A	1.401 (8)	C12A—H14	0.9600
F1B—B1B	1.389 (8)	C12A—H15	0.9600
F2B—B1B	1.388 (9)	C13B—H43	0.9600
F2A—B1A	1.404 (8)	C13B—H44	0.9600
N1A—C1A	1.334 (8)	C13B—H45	0.9600
N1A—C4A	1.401 (8)	C13A—H4	0.9600
N1A—B1A	1.525 (9)	C13A—H5	0.9600
N1B—C1B	1.348 (8)	C13A—H6	0.9600
N1B—C4B	1.400 (7)	C14B—H46	0.9600
N1B—B1B	1.516 (10)	C14B—H47	0.9600
N2A—C9A	1.354 (7)	C14B—H48	0.9600
N2A—C6A	1.403 (8)	C14A—H7	0.9600
N2A—B1A	1.529 (9)	C14A—H8	0.9600
N2B—C9B	1.346 (8)	C14A—H9	0.9600
N2B—C6B	1.401 (8)	C15B—C16B	1.511 (9)
N2B—B1B	1.547 (9)	C15B—H55	0.9700
C1B—C2B	1.412 (9)	C15B—H56	0.9700
C1B—C11B	1.483 (9)	C15A—C16A	1.520 (9)
C1A—C2A	1.403 (9)	C15A—H22	0.9700
C1A—C11A	1.506 (10)	C15A—H23	0.9700
C2B—C3B	1.365 (9)	C16B—C17B	1.504 (9)
C2B—C15B	1.506 (9)	C16B—H57	0.9700
C2A—C3A	1.378 (10)	C16B—H58	0.9700
C2A—C15A	1.501 (10)	C16A—C17A	1.500 (10)
C3B—C4B	1.406 (9)	C16A—H24	0.9700
C3B—C12B	1.499 (9)	C16A—H25	0.9700
C3A—C4A	1.418 (9)	C17B—C18B	1.483 (10)
C3A—C12A	1.491 (9)	C17B—H59	0.9700
C4B—C5B	1.425 (8)	C17B—H60	0.9700
C4A—C5A	1.411 (8)	C17A—C18A	1.450 (11)
C5A—C6A	1.400 (8)	C17A—H26	0.9700
C5A—C13A	1.495 (8)	C17A—H27	0.9700
C5B—C6B	1.374 (8)	C18B—H49	0.9600
C5B—C13B	1.503 (9)	C18B—H50	0.9600
C6B—C7B	1.432 (9)	C18B—H51	0.9600
C6A—C7A	1.407 (9)	C18A—H19	0.9600
C7B—C8B	1.395 (9)	C18A—H20	0.9600
C7B—C14B	1.485 (10)	C18A—H21	0.9600
C7A—C8A	1.385 (9)	C19A—C20A	1.543 (9)
C7A—C14A	1.524 (9)	C19A—H28	0.9700
C8A—C9A	1.402 (9)	C19A—H29	0.9700
C8A—C19A	1.482 (9)	C19B—C20B	1.498 (10)
C8B—C9B	1.388 (9)	C19B—H61	0.9700
C8B—C19B	1.512 (10)	C19B—H62	0.9700
C9A—C10A	1.499 (9)	C20A—C21A	1.478 (10)
C9B—C10B	1.498 (10)	C20A—H30	0.9700
C10A—H1	0.9600	C20A—H31	0.9700
C10A—H2	0.9600	C20B—C21B	1.545 (11)
C10A—H3	0.9600	C20B—H63	0.9700
C10B—H34	0.9600	C20B—H64	0.9700
C10B—H35	0.9600	C21A—C22A	1.493 (11)
C10B—H36	0.9600	C21A—H32	0.9700
C11B—H37	0.9600	C21A—H33	0.9700
C11B—H38	0.9600	C21B—C22B	1.388 (14)
C11B—H39	0.9600	C21B—H65	0.9700
C11A—H10	0.9600	C21B—H66	0.9700
C11A—H11	0.9600	C22A—H16	0.9600
C11A—H12	0.9600	C22A—H17	0.9600
C12B—H40	0.9600	C22A—H18	0.9600
C12B—H41	0.9600	C22B—H52	0.9600
C12B—H42	0.9600	C22B—H53	0.9600
C12A—H13	0.9600	C22B—H54	0.9600
C1A—N1A—C4A	108.0 (5)	C7B—C14B—H48	109.5
C1A—N1A—B1A	126.7 (6)	H46—C14B—H48	109.5
C4A—N1A—B1A	125.0 (6)	H47—C14B—H48	109.5
C1B—N1B—C4B	107.3 (6)	C7A—C14A—H7	109.5
C1B—N1B—B1B	125.8 (6)	C7A—C14A—H8	109.5
C4B—N1B—B1B	126.8 (5)	H7—C14A—H8	109.5
C9A—N2A—C6A	108.0 (6)	C7A—C14A—H9	109.5
C9A—N2A—B1A	127.0 (6)	H7—C14A—H9	109.5
C6A—N2A—B1A	124.9 (5)	H8—C14A—H9	109.5
C9B—N2B—C6B	108.1 (6)	C2B—C15B—C16B	115.2 (6)
C9B—N2B—B1B	127.0 (6)	C2B—C15B—H55	108.5
C6B—N2B—B1B	124.9 (6)	C16B—C15B—H55	108.5
N1B—C1B—C2B	109.6 (6)	C2B—C15B—H56	108.5
N1B—C1B—C11B	122.9 (7)	C16B—C15B—H56	108.5
C2B—C1B—C11B	127.5 (7)	H55—C15B—H56	107.5
N1A—C1A—C2A	110.4 (7)	C2A—C15A—C16A	115.2 (6)
N1A—C1A—C11A	121.9 (7)	C2A—C15A—H22	108.5
C2A—C1A—C11A	127.7 (7)	C16A—C15A—H22	108.5
C3B—C2B—C1B	107.4 (6)	C2A—C15A—H23	108.5
C3B—C2B—C15B	129.0 (7)	C16A—C15A—H23	108.5
C1B—C2B—C15B	123.6 (7)	H22—C15A—H23	107.5
C3A—C2A—C1A	106.9 (6)	C17B—C16B—C15B	114.4 (6)
C3A—C2A—C15A	126.8 (7)	C17B—C16B—H57	108.7
C1A—C2A—C15A	126.3 (8)	C15B—C16B—H57	108.7
C2B—C3B—C4B	107.7 (6)	C17B—C16B—H58	108.7
C2B—C3B—C12B	123.3 (7)	C15B—C16B—H58	108.7
C4B—C3B—C12B	129.0 (7)	H57—C16B—H58	107.6
C2A—C3A—C4A	107.5 (6)	C17A—C16A—C15A	114.6 (6)
C2A—C3A—C12A	123.4 (7)	C17A—C16A—H24	108.6
C4A—C3A—C12A	129.1 (7)	C15A—C16A—H24	108.6
N1B—C4B—C3B	108.1 (5)	C17A—C16A—H25	108.6
N1B—C4B—C5B	118.4 (6)	C15A—C16A—H25	108.6
C3B—C4B—C5B	133.6 (6)	H24—C16A—H25	107.6
N1A—C4A—C5A	120.0 (6)	C18B—C17B—C16B	114.6 (7)
N1A—C4A—C3A	107.2 (6)	C18B—C17B—H59	108.6
C5A—C4A—C3A	132.8 (7)	C16B—C17B—H59	108.6
C6A—C5A—C4A	120.9 (6)	C18B—C17B—H60	108.6
C6A—C5A—C13A	119.0 (6)	C16B—C17B—H60	108.6
C4A—C5A—C13A	120.1 (6)	H59—C17B—H60	107.6
C6B—C5B—C4B	121.9 (6)	C18A—C17A—C16A	115.1 (7)
C6B—C5B—C13B	119.5 (6)	C18A—C17A—H26	108.5
C4B—C5B—C13B	118.6 (6)	C16A—C17A—H26	108.5
C5B—C6B—N2B	120.5 (6)	C18A—C17A—H27	108.5
C5B—C6B—C7B	131.9 (7)	C16A—C17A—H27	108.5
N2B—C6B—C7B	107.6 (6)	H26—C17A—H27	107.5
C5A—C6A—N2A	120.3 (6)	C17B—C18B—H49	109.5
C5A—C6A—C7A	132.9 (7)	C17B—C18B—H50	109.5
N2A—C6A—C7A	106.8 (6)	H49—C18B—H50	109.5
C8B—C7B—C6B	106.1 (6)	C17B—C18B—H51	109.5
C8B—C7B—C14B	124.8 (7)	H49—C18B—H51	109.5
C6B—C7B—C14B	129.0 (7)	H50—C18B—H51	109.5
C8A—C7A—C6A	108.9 (6)	C17A—C18A—H19	109.5
C8A—C7A—C14A	121.7 (7)	C17A—C18A—H20	109.5
C6A—C7A—C14A	129.4 (7)	H19—C18A—H20	109.5
C7A—C8A—C9A	106.2 (6)	C17A—C18A—H21	109.5
C7A—C8A—C19A	129.5 (7)	H19—C18A—H21	109.5
C9A—C8A—C19A	124.2 (7)	H20—C18A—H21	109.5
C9B—C8B—C7B	108.1 (6)	C8A—C19A—C20A	113.4 (6)
C9B—C8B—C19B	124.1 (8)	C8A—C19A—H28	108.9
C7B—C8B—C19B	127.8 (8)	C20A—C19A—H28	108.9
N2A—C9A—C8A	110.2 (6)	C8A—C19A—H29	108.9
N2A—C9A—C10A	122.4 (7)	C20A—C19A—H29	108.9
C8A—C9A—C10A	127.4 (6)	H28—C19A—H29	107.7
N2B—C9B—C8B	110.2 (6)	C20B—C19B—C8B	113.8 (6)
N2B—C9B—C10B	121.5 (7)	C20B—C19B—H61	108.8
C8B—C9B—C10B	128.4 (7)	C8B—C19B—H61	108.8
C9A—C10A—H1	109.5	C20B—C19B—H62	108.8
C9A—C10A—H2	109.5	C8B—C19B—H62	108.8
H1—C10A—H2	109.5	H61—C19B—H62	107.7
C9A—C10A—H3	109.5	C21A—C20A—C19A	115.0 (6)
H1—C10A—H3	109.5	C21A—C20A—H30	108.5
H2—C10A—H3	109.5	C19A—C20A—H30	108.5
C9B—C10B—H34	109.5	C21A—C20A—H31	108.5
C9B—C10B—H35	109.5	C19A—C20A—H31	108.5
H34—C10B—H35	109.5	H30—C20A—H31	107.5
C9B—C10B—H36	109.5	C19B—C20B—C21B	115.7 (8)
H34—C10B—H36	109.5	C19B—C20B—H63	108.4
H35—C10B—H36	109.5	C21B—C20B—H63	108.4
C1B—C11B—H37	109.5	C19B—C20B—H64	108.4
C1B—C11B—H38	109.5	C21B—C20B—H64	108.4
H37—C11B—H38	109.5	H63—C20B—H64	107.4
C1B—C11B—H39	109.5	C20A—C21A—C22A	113.7 (7)
H37—C11B—H39	109.5	C20A—C21A—H32	108.8
H38—C11B—H39	109.5	C22A—C21A—H32	108.8
C1A—C11A—H10	109.5	C20A—C21A—H33	108.8
C1A—C11A—H11	109.5	C22A—C21A—H33	108.8
H10—C11A—H11	109.5	H32—C21A—H33	107.7
C1A—C11A—H12	109.5	C22B—C21B—C20B	114.5 (11)
H10—C11A—H12	109.5	C22B—C21B—H65	108.6
H11—C11A—H12	109.5	C20B—C21B—H65	108.6
C3B—C12B—H40	109.5	C22B—C21B—H66	108.6
C3B—C12B—H41	109.5	C20B—C21B—H66	108.6
H40—C12B—H41	109.5	H65—C21B—H66	107.6
C3B—C12B—H42	109.5	C21A—C22A—H16	109.5
H40—C12B—H42	109.5	C21A—C22A—H17	109.5
H41—C12B—H42	109.5	H16—C22A—H17	109.5
C3A—C12A—H13	109.5	C21A—C22A—H18	109.5
C3A—C12A—H14	109.5	H16—C22A—H18	109.5
H13—C12A—H14	109.5	H17—C22A—H18	109.5
C3A—C12A—H15	109.5	C21B—C22B—H52	109.5
H13—C12A—H15	109.5	C21B—C22B—H53	109.5
H14—C12A—H15	109.5	H52—C22B—H53	109.5
C5B—C13B—H43	109.5	C21B—C22B—H54	109.5
C5B—C13B—H44	109.5	H52—C22B—H54	109.5
H43—C13B—H44	109.5	H53—C22B—H54	109.5
C5B—C13B—H45	109.5	F2B—B1B—F1B	109.0 (6)
H43—C13B—H45	109.5	F2B—B1B—N1B	110.6 (6)
H44—C13B—H45	109.5	F1B—B1B—N1B	111.1 (6)
C5A—C13A—H4	109.5	F2B—B1B—N2B	109.8 (6)
C5A—C13A—H5	109.5	F1B—B1B—N2B	108.9 (6)
H4—C13A—H5	109.5	N1B—B1B—N2B	107.4 (6)
C5A—C13A—H6	109.5	F1A—B1A—F2A	107.6 (6)
H4—C13A—H6	109.5	F1A—B1A—N1A	110.2 (5)
H5—C13A—H6	109.5	F2A—B1A—N1A	110.5 (6)
C7B—C14B—H46	109.5	F1A—B1A—N2A	109.9 (6)
C7B—C14B—H47	109.5	F2A—B1A—N2A	110.3 (5)
H46—C14B—H47	109.5	N1A—B1A—N2A	108.4 (5)