# Supplementary Material (ESI) for Chemical Science
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full 'Chemical Science'
_journal_coden_cambridge 1475
_journal_year ?
_journal_volume ?
_journal_page_first ?
loop_
_publ_author_name
_publ_author_address
'Joyram Guin'
; Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1211 Geneva 4
Switzerland
;
'Celine Besnard'
; Laboratory of X-ray Crystallography
University of Geneva
24, quai E. Ansermet
CH - 1211 Geneva 4
Switzerland
;
'Philip Pattison'
; Laboratoire de Cristallographie
EPFL, CH-1015 Lausanne, Switzerland
and Swiss-Norwegian Beamline, ESRF, BP-220
F-38043 Grenoble Cedex, France
;
'Jerome Lacour'
; Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1211 Geneva 4
Switzerland
;
_publ_contact_author
;
Prof. Jerome Lacour
Department of Organic Chemistry
University of Geneva
30, quai E. Ansermet
CH - 1212 Geneva 4
Switzerland
;
_publ_contact_author_email Jerome.Lacour@unige.ch
_publ_contact_author_phone '41 22 379 60 62'
_publ_contact_author_name 'Prof. Jerome Lacour'
data_1
_database_code_depnum_ccdc_archive 'CCDC 775297'
# start Validation Reply Form ...
_vrf_PLAT027_1
;
PROBLEM: _diffrn_reflns_theta_full (too) Low ............ 23.54 Deg.
RESPONSE: data were collected using a single-axis diffractometer without
possibility to move the detector position. We were therefore limited by the
experimental setting. However, the data are of sufficient quality for the
structural analysis made on this compound.
;
# end Validation Reply Form
#Added by publCIF (CCDC output) (ven. 23. avr. 17:46:56 2010)
_audit_update_record
;
2010-04-23 # Formatted by publCIF
;
_exptl_special_details
;
Data were collected on a mar IP detector
at the Swiss Norwegian Beamline
at E.S.R.F (Grenoble, France) using
a Phi rotation.
;
_refine_special_details
;
On the difference Fourier map, disorder was observed
for the BF4- anion. The anion was modelled using
two entities with both the B and one F in common.
The occupancy for both entiities refined to
0.80(1)/0.20(1). Restrains were applied to make
distances and angles equal for both entities. Anisotropic
displacement parameters of atoms of different entities
close to each other were also restrained
to be equal.
;
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a 10.639(5)
_cell_length_b 14.831(5)
_cell_length_c 20.681(5)
_cell_angle_alpha 90
_cell_angle_beta 96.240(15)
_cell_angle_gamma 90
_cell_volume 3244(2)
_symmetry_cell_setting Monoclinic
_symmetry_space_group_name_H-M 'P 1 21/n 1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,-z+1/2
x+1/2,-y+1/2,z+1/2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
B 0.0013 0.0007 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403
-0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 4
# Given Formula = C34 H3 B1 F2 N10 O6
# Dc = 1.43 Fooo = 1344.00 Mu = 1.10 M = 696.27
# Found Formula = C36 H41 B1 F4 N2 O3
# Dc = 1.30 FOOO = 1344.00 Mu = 0.97 M = 636.54
_chemical_formula_sum 'C36 H41 B1 F4 N2 O3'
_chemical_formula_moiety 'C33 H33 N2 O2, C3 H8 O, B F4 '
_chemical_compound_source ?
_chemical_formula_weight 636.54
_cell_measurement_reflns_used 36177
_cell_measurement_theta_min 1.671
_cell_measurement_theta_max 23.561
_cell_measurement_temperature 100
_exptl_crystal_description needle
_exptl_crystal_colour black
_exptl_crystal_size_min 0.020
_exptl_crystal_size_mid 0.020
_exptl_crystal_size_max 0.300
_exptl_crystal_density_diffrn 1.303
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 1344
_exptl_absorpt_coefficient_mu 0.097
# Sheldrick geometric approximatio 1.00 1.00
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_diffrn_measurement_device 'mar 345 image plate'
_diffrn_measurement_device_type Serial
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type synchrotron
_diffrn_radiation_wavelength 0.70150
_diffrn_measurement_method '\f scans'
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'MAR345 control software (marresearch)'
_computing_cell_refinement 'CRYSALIS (Oxford Diffraction 2004)'
_computing_data_reduction 'CRYSALIS (Oxford Diffraction 2004)'
_computing_structure_solution 'Sir2004 (Burla et al., 2005)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 100
_diffrn_reflns_number 36177
_reflns_number_total 4951
_diffrn_reflns_av_R_equivalents 0.044
# Number of reflections with Friedels Law is 4951
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 5028
_diffrn_reflns_theta_min 1.671
_diffrn_reflns_theta_max 23.561
_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full 23.542
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -16
_diffrn_reflns_limit_k_max 16
_diffrn_reflns_limit_l_min -23
_diffrn_reflns_limit_l_max 23
_reflns_limit_h_min -11
_reflns_limit_h_max 11
_reflns_limit_k_min 0
_reflns_limit_k_max 16
_reflns_limit_l_min 0
_reflns_limit_l_max 23
_oxford_diffrn_Wilson_B_factor 1.66
_oxford_diffrn_Wilson_scale 0.41
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.35
_refine_diff_density_max 0.39
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 4931
_refine_ls_number_restraints 18
_refine_ls_number_parameters 443
_oxford_refine_ls_R_factor_ref 0.0479
_refine_ls_wR_factor_ref 0.0624
_refine_ls_goodness_of_fit_ref 1.1999
_refine_ls_shift/su_max 0.0004541
# The values computed from all data
_oxford_reflns_number_all 4931
_refine_ls_R_factor_all 0.0479
_refine_ls_wR_factor_all 0.0624
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 3804
_refine_ls_R_factor_gt 0.0388
_refine_ls_wR_factor_gt 0.0580
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment . # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
69.0 87.7 21.6
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Oxford Diffraction (2004). CrysAlis. Oxford Diffraction Poland, Wroclaw,
Poland.
Betteridge, P. W., Carruthers, J. R., Cooper, R. I., Prout, K. & Watkin, D. J.
(2003). J. Appl. Cryst. 36, 1487--?.
Burla, M. C. , Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., D
Caro, L. , Giacovazzo, C., Polidori, G., & Spagna R. J. Appl. Cryst. (2005).
381-388.
Prince, E. Mathematical Techniques in Crystallography and Materials Science
Springer-Verlag, New York, 1982.
Watkin, D. J. (1994). Acta Cryst. A50, 411--437.
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
F1 F 0.7677(5) 0.8749(5) 0.7451(3) 0.0330 0.803(11) Uani D U P . 1 . .
F2 F 0.729(2) 0.876(2) 0.7489(14) 0.0424 0.197(11) Uani D U P . 2 . .
B3 B 0.7336(2) 0.78868(17) 0.76341(11) 0.0250 1.0000 Uani . . . . . . .
F4 F 0.63076(12) 0.75432(9) 0.72449(6) 0.0374 1.0000 Uani D . . . . . .
F5 F 0.7190(5) 0.7806(3) 0.82840(13) 0.0522 0.803(11) Uani D U P . 1 . .
F6 F 0.6673(17) 0.8164(12) 0.8227(7) 0.0492 0.197(11) Uani D U P . 2 . .
F7 F 0.8236(13) 0.7363(10) 0.7850(10) 0.0620 0.197(11) Uani D U P . 2 . .
F8 F 0.8375(3) 0.7345(2) 0.7501(3) 0.0626 0.803(11) Uani D U P . 1 . .
O9 O 0.70972(12) 1.10897(9) 0.34784(6) 0.0202 1.0000 Uani . . . . . . .
C10 C 0.69981(18) 1.13937(13) 0.40942(9) 0.0177 1.0000 Uani . . . . . . .
C11 C 0.65667(19) 1.22314(13) 0.42315(9) 0.0204 1.0000 Uani . . . . . . .
C12 C 0.63710(19) 1.24545(14) 0.48720(9) 0.0225 1.0000 Uani . . . . . . .
C13 C 0.65261(18) 1.18243(13) 0.53633(9) 0.0198 1.0000 Uani . . . . . . .
C14 C 0.69256(18) 1.09475(13) 0.52266(9) 0.0170 1.0000 Uani . . . . . . .
C15 C 0.73016(17) 1.07377(13) 0.46017(9) 0.0159 1.0000 Uani . . . . . . .
C16 C 0.78419(18) 0.98654(13) 0.45019(9) 0.0157 1.0000 Uani . . . . . . .
C17 C 0.75363(17) 0.91694(13) 0.49218(9) 0.0153 1.0000 Uani . . . . . . .
C18 C 0.77059(18) 0.82471(13) 0.47596(9) 0.0171 1.0000 Uani . . . . . . .
N19 N 0.82023(15) 0.80468(10) 0.41784(7) 0.0171 1.0000 Uani . . . . . . .
C20 C 0.87408(18) 0.87099(13) 0.38261(9) 0.0179 1.0000 Uani . . . . . . .
C21 C 0.86473(18) 0.96287(13) 0.40043(9) 0.0167 1.0000 Uani . . . . . . .
C22 C 0.94076(18) 1.02644(13) 0.37015(9) 0.0181 1.0000 Uani . . . . . . .
O23 O 0.95184(12) 1.10931(9) 0.39839(6) 0.0199 1.0000 Uani . . . . . . .
C24 C 0.9973(2) 1.18111(13) 0.36017(10) 0.0245 1.0000 Uani . . . . . . .
H25 H 0.9851 1.2374 0.3829 0.0377 1.0000 Uiso R . . . . . .
H26 H 1.0863 1.1716 0.3541 0.0376 1.0000 Uiso R . . . . . .
H27 H 0.9441 1.1825 0.3185 0.0368 1.0000 Uiso R . . . . . .
C28 C 1.00337(19) 1.00160(13) 0.31792(9) 0.0212 1.0000 Uani . . . . . . .
C29 C 0.99878(19) 0.91147(14) 0.29727(9) 0.0226 1.0000 Uani . . . . . . .
C30 C 0.93851(19) 0.84645(13) 0.32887(9) 0.0210 1.0000 Uani . . . . . . .
H31 H 0.9398 0.7850 0.3166 0.0271 1.0000 Uiso R . . . . . .
H32 H 1.0425 0.8947 0.2610 0.0288 1.0000 Uiso R . . . . . .
H33 H 1.0528 1.0454 0.2972 0.0266 1.0000 Uiso R . . . . . .
C34 C 0.83047(19) 0.70980(13) 0.40094(9) 0.0179 1.0000 Uani . . . . . . .
C35 C 0.9407(2) 0.66310(14) 0.42340(9) 0.0222 1.0000 Uani . . . . . . .
C36 C 0.9451(2) 0.57113(14) 0.41026(10) 0.0278 1.0000 Uani . . . . . . .
C37 C 0.8438(2) 0.52585(14) 0.37631(10) 0.0284 1.0000 Uani . . . . . . .
C38 C 0.7366(2) 0.57472(14) 0.35455(10) 0.0257 1.0000 Uani . . . . . . .
C39 C 0.7265(2) 0.66693(14) 0.36640(9) 0.0216 1.0000 Uani . . . . . . .
C40 C 0.6081(2) 0.71741(16) 0.34371(11) 0.0324 1.0000 Uani . . . . . . .
H41 H 0.5490 0.6799 0.3140 0.0524 1.0000 Uiso R . . . . . .
H42 H 0.5635 0.7352 0.3810 0.0521 1.0000 Uiso R . . . . . .
H43 H 0.6286 0.7737 0.3205 0.0524 1.0000 Uiso R . . . . . .
H44 H 0.6661 0.5446 0.3313 0.0333 1.0000 Uiso R . . . . . .
C45 C 0.8513(3) 0.42549(15) 0.36453(12) 0.0433 1.0000 Uani . . . . . . .
H46 H 0.7928 0.4095 0.3277 0.0665 1.0000 Uiso R . . . . . .
H47 H 0.8266 0.3926 0.4012 0.0656 1.0000 Uiso R . . . . . .
H48 H 0.9340 0.4050 0.3563 0.0665 1.0000 Uiso R . . . . . .
H49 H 1.0167 0.5384 0.4258 0.0350 1.0000 Uiso R . . . . . .
C50 C 1.0516(2) 0.71080(15) 0.45971(10) 0.0306 1.0000 Uani . . . . . . .
H51 H 1.1104 0.6668 0.4779 0.0486 1.0000 Uiso R . . . . . .
H52 H 1.0234 0.7485 0.4944 0.0475 1.0000 Uiso R . . . . . .
H53 H 1.0937 0.7501 0.4314 0.0486 1.0000 Uiso R . . . . . .
C54 C 0.73338(18) 0.75615(14) 0.51598(9) 0.0205 1.0000 Uani . . . . . . .
C55 C 0.68369(19) 0.77925(14) 0.57311(9) 0.0220 1.0000 Uani . . . . . . .
C56 C 0.66972(18) 0.86790(13) 0.59207(9) 0.0199 1.0000 Uani . . . . . . .
C57 C 0.70328(18) 0.93783(13) 0.55195(9) 0.0169 1.0000 Uani . . . . . . .
N58 N 0.69413(15) 1.02729(11) 0.56930(7) 0.0168 1.0000 Uani . . . . . . .
C59 C 0.66256(18) 1.04882(14) 0.63599(9) 0.0189 1.0000 Uani . . . . . . .
C60 C 0.52017(18) 1.04710(14) 0.63975(9) 0.0214 1.0000 Uani . . . . . . .
C61 C 0.4890(2) 1.05114(16) 0.71035(9) 0.0283 1.0000 Uani . . . . . . .
H62 H 0.3965 1.0529 0.7117 0.0438 1.0000 Uiso R . . . . . .
H63 H 0.5282 1.1063 0.7317 0.0423 1.0000 Uiso R . . . . . .
H64 H 0.5248 0.9977 0.7348 0.0442 1.0000 Uiso R . . . . . .
H65 H 0.4823 1.0981 0.6142 0.0256 1.0000 Uiso R . . . . . .
H66 H 0.4864 0.9905 0.6194 0.0265 1.0000 Uiso R . . . . . .
H67 H 0.6969 1.1072 0.6480 0.0245 1.0000 Uiso R . . . . . .
H68 H 0.7062 1.0033 0.6646 0.0241 1.0000 Uiso R . . . . . .
H69 H 0.6357 0.8823 0.6311 0.0254 1.0000 Uiso R . . . . . .
H70 H 0.6591 0.7334 0.6005 0.0285 1.0000 Uiso R . . . . . .
H71 H 0.7391 0.6957 0.5047 0.0253 1.0000 Uiso R . . . . . .
H72 H 0.6356 1.1986 0.5785 0.0247 1.0000 Uiso R . . . . . .
H73 H 0.6101 1.3047 0.4974 0.0265 1.0000 Uiso R . . . . . .
H74 H 0.6407 1.2657 0.3897 0.0244 1.0000 Uiso R . . . . . .
C75 C 0.6631(2) 1.16781(14) 0.29506(9) 0.0266 1.0000 Uani . . . . . . .
H76 H 0.6719 1.1335 0.2548 0.0384 1.0000 Uiso R . . . . . .
H77 H 0.7172 1.2223 0.2949 0.0393 1.0000 Uiso R . . . . . .
H78 H 0.5739 1.1852 0.2994 0.0396 1.0000 Uiso R . . . . . .
O79 O 0.35122(17) 0.58660(11) 0.41232(8) 0.0471 1.0000 Uani . . . . . . .
C80 C 0.3718(2) 0.50823(14) 0.37464(10) 0.0305 1.0000 Uani . . . . . . .
C81 C 0.2495(2) 0.45780(16) 0.35663(11) 0.0390 1.0000 Uani . . . . . . .
H82 H 0.2611 0.4042 0.3298 0.0596 1.0000 Uiso R . . . . . .
H83 H 0.2152 0.4375 0.3962 0.0587 1.0000 Uiso R . . . . . .
H84 H 0.1886 0.4974 0.3325 0.0590 1.0000 Uiso R . . . . . .
C85 C 0.4692(2) 0.45132(16) 0.41496(11) 0.0363 1.0000 Uani . . . . . . .
H86 H 0.4873 0.3985 0.3888 0.0555 1.0000 Uiso R . . . . . .
H87 H 0.5480 0.4843 0.4266 0.0552 1.0000 Uiso R . . . . . .
H88 H 0.4339 0.4313 0.4551 0.0549 1.0000 Uiso R . . . . . .
H89 H 0.4086 0.5273 0.3339 0.0376 1.0000 Uiso R . . . . . .
H90 H 0.3078 0.6256 0.3900 0.0710 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.047(2) 0.0281(13) 0.0247(13) 0.0060(10) 0.0065(16) -0.0138(18)
F2 0.080(10) 0.022(5) 0.024(5) 0.001(4) 0.000(8) -0.020(9)
B3 0.0280(15) 0.0245(14) 0.0212(13) 0.0072(10) -0.0039(11) -0.0055(11)
F4 0.0326(8) 0.0477(9) 0.0303(7) 0.0089(6) -0.0043(6) -0.0123(7)
F5 0.090(3) 0.047(2) 0.0179(10) 0.0077(12) 0.0007(14) -0.0287(18)
F6 0.074(7) 0.049(7) 0.030(5) -0.009(5) 0.029(5) -0.032(5)
F7 0.029(5) 0.064(5) 0.089(8) 0.024(7) -0.009(6) 0.019(4)
F8 0.0356(14) 0.0593(14) 0.092(3) 0.004(2) 0.0024(17) 0.0154(11)
O9 0.0243(8) 0.0219(8) 0.0141(7) 0.0013(6) 0.0014(6) 0.0037(6)
C10 0.0149(11) 0.0206(11) 0.0177(10) -0.0020(8) 0.0021(8) -0.0019(8)
C11 0.0207(11) 0.0177(11) 0.0226(11) 0.0019(8) 0.0017(9) -0.0002(9)
C12 0.0231(12) 0.0182(11) 0.0264(11) -0.0028(9) 0.0028(9) 0.0014(9)
C13 0.0178(11) 0.0214(11) 0.0200(11) -0.0066(9) 0.0020(8) -0.0017(9)
C14 0.0138(11) 0.0197(11) 0.0167(10) -0.0022(8) -0.0012(8) -0.0026(8)
C15 0.0124(10) 0.0173(10) 0.0177(10) -0.0007(8) 0.0010(8) -0.0012(8)
C16 0.0131(10) 0.0188(10) 0.0137(9) -0.0036(8) -0.0048(8) -0.0025(8)
C17 0.0107(10) 0.0197(11) 0.0145(10) -0.0007(8) -0.0033(8) -0.0002(8)
C18 0.0137(11) 0.0198(11) 0.0171(10) -0.0024(8) -0.0013(8) 0.0006(8)
N19 0.0202(9) 0.0160(9) 0.0151(8) -0.0005(7) 0.0029(7) 0.0001(7)
C20 0.0184(11) 0.0186(11) 0.0159(10) 0.0006(8) -0.0016(8) 0.0003(9)
C21 0.0190(11) 0.0179(11) 0.0126(10) 0.0006(8) -0.0011(8) 0.0019(8)
C22 0.0172(11) 0.0181(11) 0.0182(10) 0.0008(8) -0.0015(8) 0.0026(8)
O23 0.0210(8) 0.0165(7) 0.0225(7) -0.0007(6) 0.0036(6) -0.0024(6)
C24 0.0263(12) 0.0174(11) 0.0301(12) 0.0025(9) 0.0053(9) -0.0032(9)
C28 0.0213(12) 0.0213(11) 0.0215(11) 0.0033(9) 0.0049(9) -0.0002(9)
C29 0.0265(12) 0.0247(12) 0.0174(10) 0.0008(9) 0.0060(9) 0.0018(9)
C30 0.0251(12) 0.0198(11) 0.0183(10) -0.0020(8) 0.0032(9) 0.0018(9)
C34 0.0241(11) 0.0143(10) 0.0167(10) 0.0002(8) 0.0085(8) 0.0004(9)
C35 0.0253(12) 0.0228(11) 0.0198(11) 0.0018(9) 0.0083(9) 0.0037(9)
C36 0.0323(13) 0.0258(12) 0.0272(12) 0.0069(9) 0.0120(10) 0.0092(10)
C37 0.0433(15) 0.0186(11) 0.0267(12) 0.0010(9) 0.0189(11) -0.0007(10)
C38 0.0321(13) 0.0230(12) 0.0231(11) -0.0044(9) 0.0081(9) -0.0089(10)
C39 0.0259(12) 0.0225(11) 0.0169(10) -0.0015(9) 0.0047(9) -0.0011(9)
C40 0.0277(13) 0.0339(14) 0.0346(13) -0.0058(10) -0.0005(10) 0.0001(10)
C45 0.0648(19) 0.0202(13) 0.0483(15) 0.0010(11) 0.0222(14) -0.0012(12)
C50 0.0262(13) 0.0352(13) 0.0296(12) 0.0018(10) -0.0009(10) 0.0035(10)
C54 0.0231(12) 0.0186(11) 0.0198(10) 0.0003(9) 0.0024(8) -0.0014(9)
C55 0.0232(12) 0.0233(12) 0.0195(11) 0.0048(9) 0.0021(9) -0.0019(9)
C56 0.0199(11) 0.0235(11) 0.0163(10) -0.0009(9) 0.0024(8) 0.0028(9)
C57 0.0129(10) 0.0203(11) 0.0168(10) -0.0014(8) -0.0017(8) -0.0005(8)
N58 0.0181(9) 0.0184(9) 0.0140(8) -0.0018(7) 0.0019(7) 0.0003(7)
C59 0.0202(11) 0.0227(11) 0.0137(10) -0.0038(8) 0.0018(8) 0.0014(9)
C60 0.0207(11) 0.0262(11) 0.0175(10) -0.0025(9) 0.0021(8) 0.0004(9)
C61 0.0262(13) 0.0376(13) 0.0219(11) -0.0028(10) 0.0060(9) -0.0009(10)
C75 0.0352(13) 0.0268(12) 0.0176(11) 0.0052(9) 0.0022(9) 0.0072(10)
O79 0.0764(14) 0.0288(9) 0.0329(9) -0.0086(8) -0.0081(9) 0.0131(9)
C80 0.0427(15) 0.0236(12) 0.0249(12) -0.0016(10) 0.0021(10) 0.0051(10)
C81 0.0409(15) 0.0334(14) 0.0405(14) 0.0011(11) -0.0058(11) 0.0059(12)
C85 0.0351(14) 0.0340(14) 0.0385(14) 0.0047(11) -0.0015(11) 0.0006(11)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 1.672(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . B3 . 1.393(8) yes
F2 . B3 . 1.33(3) yes
B3 . F4 . 1.383(3) yes
B3 . F5 . 1.375(4) yes
B3 . F8 . 1.418(4) yes
O9 . C10 . 1.366(2) yes
O9 . C75 . 1.443(2) yes
C10 . C11 . 1.365(3) yes
C10 . C15 . 1.442(3) yes
C11 . C12 . 1.403(3) yes
C11 . H74 . 0.938 no
C12 . C13 . 1.377(3) yes
C12 . H73 . 0.956 no
C13 . C14 . 1.406(3) yes
C13 . H72 . 0.941 no
C14 . C15 . 1.428(3) yes
C14 . N58 . 1.389(2) yes
C15 . C16 . 1.440(3) yes
C16 . C17 . 1.409(3) yes
C16 . C21 . 1.452(3) yes
C17 . C18 . 1.424(3) yes
C17 . C57 . 1.434(3) yes
C18 . N19 . 1.396(2) yes
C18 . C54 . 1.395(3) yes
N19 . C20 . 1.385(2) yes
N19 . C34 . 1.457(2) yes
C20 . C21 . 1.418(3) yes
C20 . C30 . 1.415(3) yes
C21 . C22 . 1.430(3) yes
C22 . O23 . 1.360(2) yes
C22 . C28 . 1.379(3) yes
O23 . C24 . 1.441(2) yes
C24 . H25 . 0.974 no
C24 . H26 . 0.978 no
C24 . H27 . 0.978 no
C28 . C29 . 1.402(3) yes
C28 . H33 . 0.966 no
C29 . C30 . 1.364(3) yes
C29 . H32 . 0.958 no
C30 . H31 . 0.947 no
C34 . C35 . 1.398(3) yes
C34 . C39 . 1.403(3) yes
C35 . C36 . 1.393(3) yes
C35 . C50 . 1.504(3) yes
C36 . C37 . 1.393(3) yes
C36 . H49 . 0.931 no
C37 . C38 . 1.384(3) yes
C37 . C45 . 1.512(3) yes
C38 . C39 . 1.396(3) yes
C38 . H44 . 0.956 no
C39 . C40 . 1.496(3) yes
C40 . H41 . 0.999 no
C40 . H42 . 0.985 no
C40 . H43 . 0.999 no
C45 . H46 . 0.959 no
C45 . H47 . 0.963 no
C45 . H48 . 0.964 no
C50 . H51 . 0.953 no
C50 . H52 . 0.981 no
C50 . H53 . 0.968 no
C54 . C55 . 1.389(3) yes
C54 . H71 . 0.931 no
C55 . C56 . 1.385(3) yes
C55 . H70 . 0.940 no
C56 . C57 . 1.399(3) yes
C56 . H69 . 0.945 no
C57 . N58 . 1.380(2) yes
N58 . C59 . 1.489(2) yes
C59 . C60 . 1.525(3) yes
C59 . H67 . 0.961 no
C59 . H68 . 0.980 no
C60 . C61 . 1.533(3) yes
C60 . H65 . 0.983 no
C60 . H66 . 0.989 no
C61 . H62 . 0.988 no
C61 . H63 . 0.999 no
C61 . H64 . 0.993 no
C75 . H76 . 0.990 no
C75 . H77 . 0.992 no
C75 . H78 . 0.997 no
O79 . C80 . 1.430(3) yes
O79 . H90 . 0.845 no
C80 . C81 . 1.512(3) yes
C80 . C85 . 1.514(3) yes
C80 . H89 . 1.008 no
C81 . H82 . 0.985 no
C81 . H83 . 0.979 no
C81 . H84 . 0.971 no
C85 . H86 . 0.982 no
C85 . H87 . 0.978 no
C85 . H88 . 0.993 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . B3 . F4 . 113.2(3) yes
F1 . B3 . F5 . 113.9(4) yes
F4 . B3 . F5 . 111.7(2) yes
F1 . B3 . F8 . 103.7(4) yes
F4 . B3 . F8 . 105.2(2) yes
F5 . B3 . F8 . 108.3(2) yes
C10 . O9 . C75 . 116.80(15) yes
O9 . C10 . C11 . 123.79(17) yes
O9 . C10 . C15 . 114.97(16) yes
C11 . C10 . C15 . 121.10(17) yes
C10 . C11 . C12 . 119.93(18) yes
C10 . C11 . H74 . 119.9 no
C12 . C11 . H74 . 120.2 no
C11 . C12 . C13 . 121.23(19) yes
C11 . C12 . H73 . 120.3 no
C13 . C12 . H73 . 118.5 no
C12 . C13 . C14 . 119.59(18) yes
C12 . C13 . H72 . 119.5 no
C14 . C13 . H72 . 121.0 no
C13 . C14 . C15 . 120.26(17) yes
C13 . C14 . N58 . 120.51(16) yes
C15 . C14 . N58 . 119.22(17) yes
C10 . C15 . C14 . 116.69(17) yes
C10 . C15 . C16 . 124.29(17) yes
C14 . C15 . C16 . 118.75(17) yes
C15 . C16 . C17 . 116.58(17) yes
C15 . C16 . C21 . 126.47(17) yes
C17 . C16 . C21 . 116.94(17) yes
C16 . C17 . C18 . 120.97(17) yes
C16 . C17 . C57 . 120.38(17) yes
C18 . C17 . C57 . 118.64(17) yes
C17 . C18 . N19 . 118.45(17) yes
C17 . C18 . C54 . 120.59(17) yes
N19 . C18 . C54 . 120.91(17) yes
C18 . N19 . C20 . 121.25(16) yes
C18 . N19 . C34 . 117.21(15) yes
C20 . N19 . C34 . 120.92(15) yes
N19 . C20 . C21 . 120.07(17) yes
N19 . C20 . C30 . 119.60(17) yes
C21 . C20 . C30 . 120.33(18) yes
C16 . C21 . C20 . 118.68(17) yes
C16 . C21 . C22 . 123.81(17) yes
C20 . C21 . C22 . 117.44(17) yes
C21 . C22 . O23 . 115.74(16) yes
C21 . C22 . C28 . 120.73(18) yes
O23 . C22 . C28 . 123.43(18) yes
C22 . O23 . C24 . 116.79(14) yes
O23 . C24 . H25 . 107.3 no
O23 . C24 . H26 . 110.6 no
H25 . C24 . H26 . 111.5 no
O23 . C24 . H27 . 107.6 no
H25 . C24 . H27 . 108.3 no
H26 . C24 . H27 . 111.4 no
C22 . C28 . C29 . 119.29(18) yes
C22 . C28 . H33 . 120.0 no
C29 . C28 . H33 . 120.6 no
C28 . C29 . C30 . 122.06(18) yes
C28 . C29 . H32 . 118.8 no
C30 . C29 . H32 . 119.1 no
C20 . C30 . C29 . 119.18(18) yes
C20 . C30 . H31 . 118.7 no
C29 . C30 . H31 . 122.1 no
N19 . C34 . C35 . 118.74(18) yes
N19 . C34 . C39 . 118.99(18) yes
C35 . C34 . C39 . 122.14(18) yes
C34 . C35 . C36 . 117.7(2) yes
C34 . C35 . C50 . 121.14(18) yes
C36 . C35 . C50 . 121.2(2) yes
C35 . C36 . C37 . 122.0(2) yes
C35 . C36 . H49 . 119.1 no
C37 . C36 . H49 . 118.9 no
C36 . C37 . C38 . 118.4(2) yes
C36 . C37 . C45 . 120.3(2) yes
C38 . C37 . C45 . 121.3(2) yes
C37 . C38 . C39 . 122.2(2) yes
C37 . C38 . H44 . 119.5 no
C39 . C38 . H44 . 118.3 no
C34 . C39 . C38 . 117.5(2) yes
C34 . C39 . C40 . 121.57(18) yes
C38 . C39 . C40 . 120.9(2) yes
C39 . C40 . H41 . 111.5 no
C39 . C40 . H42 . 110.4 no
H41 . C40 . H42 . 107.9 no
C39 . C40 . H43 . 110.4 no
H41 . C40 . H43 . 109.0 no
H42 . C40 . H43 . 107.6 no
C37 . C45 . H46 . 109.3 no
C37 . C45 . H47 . 110.4 no
H46 . C45 . H47 . 106.9 no
C37 . C45 . H48 . 113.9 no
H46 . C45 . H48 . 107.9 no
H47 . C45 . H48 . 108.2 no
C35 . C50 . H51 . 108.7 no
C35 . C50 . H52 . 110.4 no
H51 . C50 . H52 . 110.0 no
C35 . C50 . H53 . 111.7 no
H51 . C50 . H53 . 108.8 no
H52 . C50 . H53 . 107.2 no
C18 . C54 . C55 . 118.92(19) yes
C18 . C54 . H71 . 121.6 no
C55 . C54 . H71 . 119.5 no
C54 . C55 . C56 . 122.53(19) yes
C54 . C55 . H70 . 119.3 no
C56 . C55 . H70 . 118.1 no
C55 . C56 . C57 . 119.60(18) yes
C55 . C56 . H69 . 121.3 no
C57 . C56 . H69 . 119.0 no
C17 . C57 . C56 . 119.65(17) yes
C17 . C57 . N58 . 118.38(17) yes
C56 . C57 . N58 . 121.92(17) yes
C14 . N58 . C57 . 120.52(15) yes
C14 . N58 . C59 . 120.12(15) yes
C57 . N58 . C59 . 118.43(15) yes
N58 . C59 . C60 . 111.64(15) yes
N58 . C59 . H67 . 108.3 no
C60 . C59 . H67 . 110.7 no
N58 . C59 . H68 . 105.7 no
C60 . C59 . H68 . 111.4 no
H67 . C59 . H68 . 108.8 no
C59 . C60 . C61 . 111.50(16) yes
C59 . C60 . H65 . 108.1 no
C61 . C60 . H65 . 111.3 no
C59 . C60 . H66 . 108.0 no
C61 . C60 . H66 . 109.4 no
H65 . C60 . H66 . 108.4 no
C60 . C61 . H62 . 110.3 no
C60 . C61 . H63 . 109.2 no
H62 . C61 . H63 . 109.6 no
C60 . C61 . H64 . 110.0 no
H62 . C61 . H64 . 109.5 no
H63 . C61 . H64 . 108.1 no
O9 . C75 . H76 . 105.7 no
O9 . C75 . H77 . 110.1 no
H76 . C75 . H77 . 107.9 no
O9 . C75 . H78 . 109.9 no
H76 . C75 . H78 . 112.8 no
H77 . C75 . H78 . 110.3 no
C80 . O79 . H90 . 111.5 no
O79 . C80 . C81 . 110.95(19) yes
O79 . C80 . C85 . 106.82(18) yes
C81 . C80 . C85 . 112.26(19) yes
O79 . C80 . H89 . 108.9 no
C81 . C80 . H89 . 109.6 no
C85 . C80 . H89 . 108.2 no
C80 . C81 . H82 . 112.4 no
C80 . C81 . H83 . 109.6 no
H82 . C81 . H83 . 107.7 no
C80 . C81 . H84 . 109.6 no
H82 . C81 . H84 . 108.4 no
H83 . C81 . H84 . 109.0 no
C80 . C85 . H86 . 107.7 no
C80 . C85 . H87 . 111.9 no
H86 . C85 . H87 . 108.6 no
C80 . C85 . H88 . 109.2 no
H86 . C85 . H88 . 109.7 no
H87 . C85 . H88 . 109.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C12 . H73 . O79 2_676 138 0.96 2.47 3.238(3) yes
# Attachment 'web_deposit_cif_file_1_JeromeLacour_1287092705.cif'
data_1a
_database_code_depnum_ccdc_archive 'CCDC 775298'
_exptl_special_details
;
;
_refine_special_details
;
One of the CF3 group is slightly disordered. The difference fourier map
revealed a second CF3 which was included in the refinement. The final
occupancy factors for the two CF3 groups were 0.915/0.085. Even if the
second CF3 group is minor, it was kept in the model since it improved
the R values and appeared clearly in the fourier difference map. The
refinement of the CF* group was made by includind similarity restrains
on the bond and the angle between the two groups and on opposite anisotropic
displacement parameters.
H atom position were calculated, allowed to refined with geometrical restrains
for a few cycles and they were ride on their belonging atom
for the rest of the refinement.
The crystal selected was larger than the beam but the crystals were soft and
cutting them resulted in lowest quality diffraction data.
;
# End of 'script/refcif.dat'
#end of refcif
_cell_length_a 8.641(2)
_cell_length_b 12.453(3)
_cell_length_c 16.039(3)
_cell_angle_alpha 91.073(4)
_cell_angle_beta 92.167(10)
_cell_angle_gamma 100.384(11)
_cell_volume 1695.8(7)
_symmetry_cell_setting Triclinic
_symmetry_space_group_name_H-M 'P -1 '
_symmetry_space_group_name_Hall ?
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
_cell_formula_units_Z 2
# Given Formula = C80 H20 F5 N1.50 O4
# Dc = 2.27 Fooo = 732.00 Mu = 1.59 M = 1161.04
# Found Formula = C41 H36 F6 N2 O2
# Dc = 1.38 FOOO = 732.00 Mu = 1.07 M = 702.74
_chemical_formula_sum 'C41 H36 F6 N2 O2'
_chemical_formula_moiety 'C41 H36 F6 N2 O2'
_chemical_compound_source ?
_chemical_formula_weight 702.74
_cell_measurement_reflns_used 11705
_cell_measurement_theta_min 6
_cell_measurement_theta_max 26
_cell_measurement_temperature 120
_exptl_crystal_description rectangle
_exptl_crystal_colour brown
_exptl_crystal_size_min 0.600
_exptl_crystal_size_mid 0.600
_exptl_crystal_size_max 0.700
_exptl_crystal_density_diffrn 1.376
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
# Non-dispersive F(000):
_exptl_crystal_F_000 732
_exptl_absorpt_coefficient_mu 0.107
# Sheldrick geometric approximatio 0.94 0.94
_exptl_absorpt_correction_type none
_exptl_absorpt_correction_T_min ?
_exptl_absorpt_correction_T_max ?
_diffrn_measurement_device 'Stoe IPDS'
_diffrn_measurement_device_type Area
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type 'Mo K\a'
_diffrn_radiation_wavelength 0.71073
_diffrn_measurement_method \w
# If a reference occurs more than once, delete the author
# and date from subsequent references.
_computing_data_collection 'IPDS (Stoe & Cie, 1996)'
_computing_cell_refinement 'XDS (Kabsch, 1988)'
_computing_data_reduction 'XDS (Kabsch 1988)'
_computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material 'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics 'CAMERON (Watkin et al., 1996)'
_diffrn_standards_interval_time .
_diffrn_standards_interval_count .
_diffrn_standards_number 0
_diffrn_standards_decay_% ?
_diffrn_ambient_temperature 120
_diffrn_reflns_number 15780
_reflns_number_total 7048
_diffrn_reflns_av_R_equivalents 0.042
# Number of reflections with Friedels Law is 7048
# Number of reflections without Friedels Law is 0
# Theoretical number of reflections is about 6395
_diffrn_reflns_theta_min 5.449
_diffrn_reflns_theta_max 26.731
_diffrn_measured_fraction_theta_max 0.978
_diffrn_reflns_theta_full 26.216
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -20
_diffrn_reflns_limit_l_max 20
_reflns_limit_h_min -10
_reflns_limit_h_max 10
_reflns_limit_k_min -15
_reflns_limit_k_max 15
_reflns_limit_l_min 0
_reflns_limit_l_max 20
_oxford_diffrn_Wilson_B_factor 1.87
_oxford_diffrn_Wilson_scale 27.02
_atom_sites_solution_primary direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary difmap
_atom_sites_solution_hydrogens geom
_refine_diff_density_min -0.32
_refine_diff_density_max 0.32
# The current dictionary definitions do not cover the
# situation where the reflections used for refinement were
# selected by a user-defined sigma threshold
# The values actually used during refinement
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_refine_ls_number_reflns 6254
_refine_ls_number_restraints 18
_refine_ls_number_parameters 488
_oxford_refine_ls_R_factor_ref 0.0486
_refine_ls_wR_factor_ref 0.0800
_refine_ls_goodness_of_fit_ref 1.1087
_refine_ls_shift/su_max 0.0015235
# The values computed from all data
_oxford_reflns_number_all 6254
_refine_ls_R_factor_all 0.0486
_refine_ls_wR_factor_all 0.0800
# The values computed with a 2 sigma cutoff - a la SHELX
_reflns_threshold_expression I>2.0\s(I)
_reflns_number_gt 5812
_refine_ls_R_factor_gt 0.0456
_refine_ls_wR_factor_gt 0.0785
# choose from: rm (reference molecule of known chirality),
# ad (anomolous dispersion - Flack), rmad (rm and ad),
# syn (from synthesis), unk (unknown) or . (not applicable).
_chemical_absolute_configuration .
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_hydrogen_treatment none # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)]
where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^
A~i~ are:
1.42 1.44 0.149
;
# Insert your own references if required - in alphabetical order
_publ_section_references
;
Betteridge, P.W., Carruthers, J.R., Cooper, R.I.,
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487.
Kabsch W. ,J. Appl. Cryst. (1988). 21, 916-924
Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.
Prince, E.
Mathematical Techniques in Crystallography
and Materials Science
Springer-Verlag, New York, 1982.
Stoe & Cie (1996). IPDS Software.
Stoe & Cie (1996). XRED V1.08.
Watkin D.J. (1994).
Acta Cryst, A50, 411-437.
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical
Crystallography Laboratory, Oxford, UK.
;
# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3
# Replace last . with number of unfound hydrogen atomsattached to an atom.
# ..._refinement_flags_...
# . no refinement constraints S special position constraint on site
# G rigid group refinement of site R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond) P partial occupancy constraint
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
F1 F 0.26317(13) 0.29208(11) 0.43952(6) 0.0402 1.0000 Uani . . . . . . .
C2 C 0.3832(2) 0.26663(15) 0.48475(10) 0.0256 1.0000 Uani . . . . . . .
F3 F 0.44047(17) 0.19276(11) 0.43966(7) 0.0527 1.0000 Uani . . . . . . .
F4 F 0.49409(15) 0.35692(11) 0.48811(7) 0.0505 1.0000 Uani . . . . . . .
C5 C 0.33660(17) 0.22803(13) 0.56957(9) 0.0187 1.0000 Uani . . . . . . .
C6 C 0.27907(17) 0.30046(12) 0.62283(9) 0.0168 1.0000 Uani . . . . . . .
C7 C 0.23360(17) 0.26898(12) 0.70223(9) 0.0146 1.0000 Uani . . . . . . .
C8 C 0.17874(17) 0.34747(12) 0.76725(9) 0.0149 1.0000 Uani . . . . . . .
C9 C 0.13300(18) 0.44596(12) 0.72258(9) 0.0156 1.0000 Uani . . . . . . .
C10 C 0.00504(18) 0.41845(12) 0.66408(9) 0.0172 1.0000 Uani . . . . . . .
N11 N -0.08344(15) 0.31116(10) 0.66608(8) 0.0179 1.0000 Uani . . . . . . .
C12 C -0.10613(18) 0.27046(12) 0.74713(9) 0.0165 1.0000 Uani . . . . . . .
C13 C 0.02547(17) 0.28990(11) 0.80259(9) 0.0149 1.0000 Uani . . . . . . .
C14 C 0.00998(18) 0.25865(12) 0.88568(9) 0.0167 1.0000 Uani . . . . . . .
N15 N 0.14026(15) 0.27803(10) 0.94133(8) 0.0177 1.0000 Uani . . . . . . .
C16 C 0.28813(18) 0.33160(12) 0.91643(9) 0.0164 1.0000 Uani . . . . . . .
C17 C 0.31063(17) 0.36827(11) 0.83492(9) 0.0153 1.0000 Uani . . . . . . .
C18 C 0.46500(18) 0.41587(12) 0.81453(9) 0.0171 1.0000 Uani . . . . . . .
O19 O 0.48096(12) 0.44447(9) 0.73308(7) 0.0205 1.0000 Uani . . . . . . .
C20 C 0.6272(2) 0.50620(16) 0.71060(11) 0.0311 1.0000 Uani . . . . . . .
H203 H 0.6149 0.5210 0.6517 0.0458 1.0000 Uiso R . . . . . .
H201 H 0.6468 0.5761 0.7423 0.0457 1.0000 Uiso R . . . . . .
H202 H 0.7145 0.4638 0.7201 0.0452 1.0000 Uiso R . . . . . .
C24 C 0.58966(18) 0.43089(13) 0.87260(10) 0.0206 1.0000 Uani . . . . . . .
C25 C 0.56239(19) 0.39687(13) 0.95338(10) 0.0223 1.0000 Uani . . . . . . .
C26 C 0.41488(19) 0.34773(12) 0.97549(10) 0.0200 1.0000 Uani . . . . . . .
H261 H 0.3969 0.3263 1.0303 0.0244 1.0000 Uiso R . . . . . .
H251 H 0.6455 0.4093 0.9937 0.0247 1.0000 Uiso R . . . . . .
H241 H 0.6908 0.4639 0.8592 0.0239 1.0000 Uiso R . . . . . .
C30 C 0.12986(18) 0.23242(13) 1.0235(1) 0.0192 1.0000 Uani . . . . . . .
C31 C 0.1790(2) 0.13297(13) 1.03639(10) 0.0224 1.0000 Uani . . . . . . .
C32 C 0.1788(2) 0.09362(14) 1.11733(11) 0.0275 1.0000 Uani . . . . . . .
C33 C 0.1306(2) 0.15037(14) 1.18393(10) 0.0260 1.0000 Uani . . . . . . .
C34 C 0.08019(19) 0.24794(14) 1.16871(10) 0.0239 1.0000 Uani . . . . . . .
C35 C 0.07907(18) 0.29093(13) 1.08894(10) 0.0196 1.0000 Uani . . . . . . .
C36 C 0.0235(2) 0.39677(14) 1.07352(11) 0.0267 1.0000 Uani . . . . . . .
H361 H 0.0103 0.4353 1.1266 0.0407 1.0000 Uiso R . . . . . .
H362 H 0.0979 0.4451 1.0397 0.0394 1.0000 Uiso R . . . . . .
H363 H -0.0755 0.3835 1.0434 0.0410 1.0000 Uiso R . . . . . .
H341 H 0.0470 0.2878 1.2145 0.0264 1.0000 Uiso R . . . . . .
C41 C 0.1356(2) 0.10595(18) 1.27097(11) 0.0393 1.0000 Uani . . . . . . .
H412 H 0.0804 0.1456 1.3088 0.0578 1.0000 Uiso R . . . . . .
H413 H 0.2430 0.1127 1.2905 0.0587 1.0000 Uiso R . . . . . .
H411 H 0.0869 0.0302 1.2708 0.0591 1.0000 Uiso R . . . . . .
H321 H 0.2121 0.0261 1.1275 0.0345 1.0000 Uiso R . . . . . .
C46 C 0.2318(2) 0.06983(14) 0.96510(11) 0.0318 1.0000 Uani . . . . . . .
H462 H 0.2691 0.0047 0.9852 0.0481 1.0000 Uiso R . . . . . .
H463 H 0.3193 0.1174 0.9385 0.0466 1.0000 Uiso R . . . . . .
H461 H 0.1461 0.0486 0.9238 0.0462 1.0000 Uiso R . . . . . .
C50 C -0.13752(18) 0.20673(12) 0.91174(10) 0.0194 1.0000 Uani . . . . . . .
C51 C -0.26537(18) 0.18756(12) 0.85581(10) 0.0204 1.0000 Uani . . . . . . .
C52 C -0.25277(18) 0.21832(12) 0.77323(10) 0.0198 1.0000 Uani . . . . . . .
H521 H -0.3415 0.2063 0.7357 0.0219 1.0000 Uiso R . . . . . .
H511 H -0.3657 0.1513 0.8734 0.0240 1.0000 Uiso R . . . . . .
H501 H -0.1479 0.1850 0.9664 0.0233 1.0000 Uiso R . . . . . .
C56 C -0.20436(19) 0.27300(13) 0.59995(10) 0.0221 1.0000 Uani . . . . . . .
C57 C -0.22947(19) 0.15015(14) 0.58135(10) 0.0247 1.0000 Uani . . . . . . .
C58 C -0.0836(2) 0.11072(15) 0.55241(12) 0.0307 1.0000 Uani . . . . . . .
H581 H -0.1091 0.0326 0.5387 0.0452 1.0000 Uiso R . . . . . .
H583 H -0.0025 0.1222 0.5957 0.0451 1.0000 Uiso R . . . . . .
H582 H -0.0436 0.1507 0.5048 0.0448 1.0000 Uiso R . . . . . .
H572 H -0.2681 0.1081 0.6312 0.0285 1.0000 Uiso R . . . . . .
H571 H -0.3103 0.1325 0.5364 0.0292 1.0000 Uiso R . . . . . .
H561 H -0.3073 0.2940 0.6136 0.0255 1.0000 Uiso R . . . . . .
H562 H -0.1684 0.3107 0.5489 0.0244 1.0000 Uiso R . . . . . .
C66 C -0.03522(19) 0.49541(13) 0.60884(10) 0.0201 1.0000 Uani . . . . . . .
C67 C 0.04707(19) 0.60124(13) 0.61495(10) 0.0229 1.0000 Uani . . . . . . .
C68 C 0.16263(19) 0.63356(13) 0.67689(10) 0.0216 1.0000 Uani . . . . . . .
C69 C 0.20245(18) 0.55697(12) 0.73277(9) 0.0179 1.0000 Uani . . . . . . .
O70 O 0.30489(13) 0.58647(8) 0.79917(7) 0.0219 1.0000 Uani . . . . . . .
C71 C 0.3800(3) 0.69763(14) 0.80747(14) 0.0411 1.0000 Uani . . . . . . .
H713 H 0.4518 0.7036 0.8576 0.0608 1.0000 Uiso R . . . . . .
H712 H 0.2984 0.7454 0.8144 0.0603 1.0000 Uiso R . . . . . .
H711 H 0.4426 0.7214 0.7592 0.0607 1.0000 Uiso R . . . . . .
H681 H 0.2135 0.7072 0.6822 0.0257 1.0000 Uiso R . . . . . .
H671 H 0.0217 0.6518 0.5765 0.0282 1.0000 Uiso R . . . . . .
H661 H -0.1187 0.4781 0.5699 0.0233 1.0000 Uiso R . . . . . .
C78 C 0.24821(17) 0.16453(12) 0.72742(9) 0.0172 1.0000 Uani . . . . . . .
C79 C 0.30696(18) 0.09376(12) 0.67439(10) 0.0191 1.0000 Uani . . . . . . .
C80 C 0.35062(18) 0.12452(13) 0.59449(10) 0.0202 1.0000 Uani . . . . . . .
H801 H 0.3876 0.0750 0.5591 0.0245 1.0000 Uiso R . . . . . .
C82 C 0.3281(2) -0.01682(13) 0.70280(11) 0.0269 1.0000 Uani . . . . . . .
F83 F 0.2550(2) -0.04700(11) 0.77152(10) 0.0467 0.915(3) Uani D U P . 1 . .
F84 F 0.2094(19) -0.0796(16) 0.713(2) 0.0829 0.085(3) Uani D U P . 2 . .
F85 F 0.2723(3) -0.09502(10) 0.64564(10) 0.0642 0.915(3) Uani D U P . 1 . .
F86 F 0.404(3) -0.0683(15) 0.6634(13) 0.0537 0.085(3) Uani D U P . 2 . .
F87 F 0.47793(17) -0.02341(14) 0.71598(18) 0.0750 0.915(3) Uani D U P . 1 . .
F88 F 0.407(3) -0.0079(12) 0.7797(12) 0.0668 0.085(3) Uani D U P . 2 . .
H781 H 0.2205 0.1426 0.7809 0.0202 1.0000 Uiso R . . . . . .
H61 H 0.2735 0.3712 0.6042 0.0196 1.0000 Uiso R . . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0351(6) 0.0680(8) 0.0232(5) 0.0127(5) -0.0018(4) 0.0240(6)
C2 0.0234(8) 0.0360(10) 0.0204(8) -0.0006(7) 0.0005(6) 0.0132(7)
F3 0.0823(10) 0.0687(9) 0.0228(6) 0.0064(5) 0.0196(6) 0.0514(8)
F4 0.0482(7) 0.0682(9) 0.0263(6) 0.0140(6) 0.0060(5) -0.0150(6)
C5 0.0155(7) 0.0232(8) 0.0182(8) -0.0012(6) -0.0006(6) 0.0058(6)
C6 0.0156(7) 0.0178(7) 0.0175(7) 0.0018(6) -0.0016(6) 0.0052(6)
C7 0.0128(7) 0.0139(7) 0.0168(7) 0.0000(6) -0.0013(5) 0.0019(5)
C8 0.0185(7) 0.0122(7) 0.0147(7) 0.0017(5) 0.0025(6) 0.0041(6)
C9 0.0193(7) 0.0157(7) 0.0137(7) 0.0031(6) 0.0045(6) 0.0068(6)
C10 0.0189(7) 0.0189(8) 0.0157(7) 0.0020(6) 0.0056(6) 0.0075(6)
N11 0.0179(6) 0.0194(6) 0.0168(6) 0.0024(5) 0.0001(5) 0.0040(5)
C12 0.0197(8) 0.0134(7) 0.0174(7) -0.0002(6) 0.0021(6) 0.0050(6)
C13 0.0167(7) 0.0105(7) 0.0181(7) 0.0008(5) 0.0029(6) 0.0040(6)
C14 0.0202(8) 0.0120(7) 0.0187(7) 0.0012(6) 0.0016(6) 0.0048(6)
N15 0.0195(7) 0.0180(6) 0.0152(6) 0.0044(5) 0.0017(5) 0.0021(5)
C16 0.0198(8) 0.0112(7) 0.0189(7) 0.0003(6) 0.0017(6) 0.0046(6)
C17 0.0188(7) 0.0105(7) 0.0172(7) 0.0003(5) 0.0007(6) 0.0048(6)
C18 0.0208(8) 0.0127(7) 0.0183(7) -0.0004(6) 0.0030(6) 0.0044(6)
O19 0.0185(5) 0.0225(6) 0.0192(5) 0.0035(4) 0.0040(4) -0.0006(4)
C20 0.0239(9) 0.0361(10) 0.0304(10) 0.0083(8) 0.0066(7) -0.0044(7)
C24 0.0171(8) 0.0180(8) 0.0263(8) -0.0010(6) 0.0020(6) 0.0019(6)
C25 0.0216(8) 0.0222(8) 0.0226(8) -0.0027(6) -0.0057(6) 0.0048(6)
C26 0.0241(8) 0.0189(8) 0.0169(7) 0.0013(6) -0.0008(6) 0.0036(6)
C30 0.0203(8) 0.0200(8) 0.0162(7) 0.0047(6) -0.0006(6) 0.0008(6)
C31 0.0268(8) 0.0181(8) 0.0218(8) 0.0037(6) 0.0002(6) 0.0027(6)
C32 0.0332(9) 0.0230(8) 0.0265(9) 0.0095(7) -0.0011(7) 0.0049(7)
C33 0.0251(9) 0.0311(9) 0.0202(8) 0.0079(7) -0.0008(7) 0.0003(7)
C34 0.0227(8) 0.0311(9) 0.0169(8) -0.0002(7) 0.0025(6) 0.0018(7)
C35 0.0176(7) 0.0209(8) 0.0199(8) 0.0017(6) 0.0007(6) 0.0017(6)
C36 0.0272(9) 0.0251(9) 0.0287(9) 0.0008(7) 0.0016(7) 0.0074(7)
C41 0.0435(12) 0.0506(12) 0.0237(10) 0.0145(9) 0.0004(8) 0.0068(10)
C46 0.0479(11) 0.0215(9) 0.0282(9) 0.0037(7) 0.0058(8) 0.0109(8)
C50 0.0231(8) 0.0173(7) 0.0179(8) 0.0034(6) 0.0053(6) 0.0029(6)
C51 0.0191(8) 0.0171(7) 0.0250(8) 0.0023(6) 0.0054(6) 0.0025(6)
C52 0.0171(7) 0.0185(8) 0.0237(8) -0.0004(6) 0.0006(6) 0.0036(6)
C56 0.0195(8) 0.0283(9) 0.0190(8) 0.0004(6) -0.0019(6) 0.0059(7)
C57 0.0200(8) 0.0306(9) 0.0222(8) -0.0050(7) -0.0027(6) 0.0028(7)
C58 0.0245(9) 0.0321(10) 0.0352(10) -0.0083(8) -0.0008(7) 0.0057(7)
C66 0.0216(8) 0.0264(8) 0.0152(7) 0.0050(6) 0.0036(6) 0.0111(6)
C67 0.0280(9) 0.0249(8) 0.0199(8) 0.0112(6) 0.0075(6) 0.0134(7)
C68 0.0287(9) 0.0151(7) 0.0229(8) 0.0054(6) 0.0068(7) 0.0071(6)
C69 0.0213(8) 0.0166(7) 0.0175(7) 0.0015(6) 0.0050(6) 0.0072(6)
O70 0.0304(6) 0.0114(5) 0.0230(6) 0.0017(4) -0.0033(5) 0.0025(4)
C71 0.0538(13) 0.0165(9) 0.0475(12) 0.0060(8) -0.0209(10) -0.0039(8)
C78 0.0176(7) 0.0158(7) 0.0179(7) 0.0022(6) 0.0001(6) 0.0025(6)
C79 0.0176(7) 0.0143(7) 0.0253(8) -0.0011(6) -0.0010(6) 0.0030(6)
C80 0.0164(7) 0.0223(8) 0.0223(8) -0.0069(6) -0.0005(6) 0.0055(6)
C82 0.0290(9) 0.0175(8) 0.0358(10) 0.0005(7) 0.0065(7) 0.0076(7)
F83 0.0797(12) 0.0266(7) 0.0434(8) 0.0176(6) 0.0288(8) 0.0279(7)
F84 0.027(6) 0.046(7) 0.175(10) 0.042(8) 0.012(8) -0.003(6)
F85 0.1300(18) 0.0143(7) 0.0452(9) -0.0068(6) -0.0020(10) 0.0064(8)
F86 0.072(8) 0.041(7) 0.062(7) 0.005(6) 0.039(7) 0.039(6)
F87 0.0293(8) 0.0394(9) 0.162(2) 0.0464(12) 0.0043(10) 0.0162(7)
F88 0.130(9) 0.016(6) 0.057(7) 0.000(5) -0.024(8) 0.025(7)
_refine_ls_extinction_method None
_oxford_refine_ls_scale 0.25471(13)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
F1 . C2 . 1.3314(19) yes
C2 . F3 . 1.334(2) yes
C2 . F4 . 1.338(2) yes
C2 . C5 . 1.497(2) yes
C5 . C6 . 1.398(2) yes
C5 . C80 . 1.381(2) yes
C6 . C7 . 1.389(2) yes
C6 . H61 . 0.944 no
C7 . C8 . 1.5602(19) yes
C7 . C78 . 1.395(2) yes
C8 . C9 . 1.536(2) yes
C8 . C13 . 1.523(2) yes
C8 . C17 . 1.527(2) yes
C9 . C10 . 1.412(2) yes
C9 . C69 . 1.408(2) yes
C10 . N11 . 1.416(2) yes
C10 . C66 . 1.398(2) yes
N11 . C12 . 1.4118(19) yes
N11 . C56 . 1.470(2) yes
C12 . C13 . 1.400(2) yes
C12 . C52 . 1.399(2) yes
C13 . C14 . 1.400(2) yes
C14 . N15 . 1.393(2) yes
C14 . C50 . 1.404(2) yes
N15 . C16 . 1.407(2) yes
N15 . C30 . 1.4439(19) yes
C16 . C17 . 1.402(2) yes
C16 . C26 . 1.404(2) yes
C17 . C18 . 1.412(2) yes
C18 . O19 . 1.3660(18) yes
C18 . C24 . 1.381(2) yes
O19 . C20 . 1.4187(19) yes
C20 . H203 . 0.972 no
C20 . H201 . 0.984 no
C20 . H202 . 1.005 no
C24 . C25 . 1.386(2) yes
C24 . H241 . 0.931 no
C25 . C26 . 1.373(2) yes
C25 . H251 . 0.938 no
C26 . H261 . 0.935 no
C30 . C31 . 1.396(2) yes
C30 . C35 . 1.396(2) yes
C31 . C32 . 1.396(2) yes
C31 . C46 . 1.506(2) yes
C32 . C33 . 1.387(2) yes
C32 . H321 . 0.951 no
C33 . C34 . 1.386(2) yes
C33 . C41 . 1.513(2) yes
C34 . C35 . 1.396(2) yes
C34 . H341 . 0.960 no
C35 . C36 . 1.504(2) yes
C36 . H361 . 0.990 no
C36 . H362 . 0.985 no
C36 . H363 . 0.952 no
C41 . H412 . 0.966 no
C41 . H413 . 0.957 no
C41 . H411 . 0.961 no
C46 . H462 . 0.981 no
C46 . H463 . 0.989 no
C46 . H461 . 0.970 no
C50 . C51 . 1.380(2) yes
C50 . H501 . 0.925 no
C51 . C52 . 1.388(2) yes
C51 . H511 . 0.958 no
C52 . H521 . 0.945 no
C56 . C57 . 1.528(2) yes
C56 . H561 . 1.002 no
C56 . H562 . 0.984 no
C57 . C58 . 1.518(2) yes
C57 . H572 . 0.999 no
C57 . H571 . 0.978 no
C58 . H581 . 0.977 no
C58 . H583 . 0.958 no
C58 . H582 . 0.961 no
C66 . C67 . 1.380(2) yes
C66 . H661 . 0.928 no
C67 . C68 . 1.382(2) yes
C67 . H671 . 0.937 no
C68 . C69 . 1.399(2) yes
C68 . H681 . 0.943 no
C69 . O70 . 1.3600(19) yes
O70 . C71 . 1.420(2) yes
C71 . H713 . 0.990 no
C71 . H712 . 1.009 no
C71 . H711 . 0.981 no
C78 . C79 . 1.387(2) yes
C78 . H781 . 0.932 no
C79 . C80 . 1.391(2) yes
C79 . C82 . 1.498(2) yes
C80 . H801 . 0.935 no
C82 . F83 . 1.318(2) yes
C82 . F85 . 1.336(2) yes
C82 . F87 . 1.321(2) yes
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
F1 . C2 . F3 . 106.46(14) yes
F1 . C2 . F4 . 105.55(15) yes
F3 . C2 . F4 . 106.23(15) yes
F1 . C2 . C5 . 112.45(14) yes
F3 . C2 . C5 . 113.13(14) yes
F4 . C2 . C5 . 112.45(14) yes
C2 . C5 . C6 . 117.75(14) yes
C2 . C5 . C80 . 121.10(14) yes
C6 . C5 . C80 . 121.15(14) yes
C5 . C6 . C7 . 120.28(14) yes
C5 . C6 . H61 . 118.8 no
C7 . C6 . H61 . 120.9 no
C6 . C7 . C8 . 123.28(13) yes
C6 . C7 . C78 . 118.52(13) yes
C8 . C7 . C78 . 118.03(13) yes
C7 . C8 . C9 . 109.63(12) yes
C7 . C8 . C13 . 108.56(12) yes
C9 . C8 . C13 . 104.11(12) yes
C7 . C8 . C17 . 104.97(11) yes
C9 . C8 . C17 . 118.46(12) yes
C13 . C8 . C17 . 110.88(12) yes
C8 . C9 . C10 . 114.00(13) yes
C8 . C9 . C69 . 128.29(14) yes
C10 . C9 . C69 . 117.71(13) yes
C9 . C10 . N11 . 117.09(13) yes
C9 . C10 . C66 . 121.09(14) yes
N11 . C10 . C66 . 121.78(14) yes
C10 . N11 . C12 . 114.28(12) yes
C10 . N11 . C56 . 119.56(13) yes
C12 . N11 . C56 . 118.82(13) yes
N11 . C12 . C13 . 116.32(13) yes
N11 . C12 . C52 . 122.75(14) yes
C13 . C12 . C52 . 120.85(14) yes
C8 . C13 . C12 . 116.20(13) yes
C8 . C13 . C14 . 124.03(13) yes
C12 . C13 . C14 . 119.75(14) yes
C13 . C14 . N15 . 120.10(13) yes
C13 . C14 . C50 . 119.23(14) yes
N15 . C14 . C50 . 120.66(14) yes
C14 . N15 . C16 . 121.26(13) yes
C14 . N15 . C30 . 120.05(13) yes
C16 . N15 . C30 . 118.33(12) yes
N15 . C16 . C17 . 121.57(13) yes
N15 . C16 . C26 . 118.34(14) yes
C17 . C16 . C26 . 120.09(14) yes
C8 . C17 . C16 . 122.06(13) yes
C8 . C17 . C18 . 120.17(13) yes
C16 . C17 . C18 . 117.46(14) yes
C17 . C18 . O19 . 114.71(13) yes
C17 . C18 . C24 . 122.25(14) yes
O19 . C18 . C24 . 123.04(14) yes
C18 . O19 . C20 . 117.82(13) yes
O19 . C20 . H203 . 106.0 no
O19 . C20 . H201 . 109.0 no
H203 . C20 . H201 . 108.6 no
O19 . C20 . H202 . 110.8 no
H203 . C20 . H202 . 110.3 no
H201 . C20 . H202 . 112.0 no
C18 . C24 . C25 . 118.79(15) yes
C18 . C24 . H241 . 121.9 no
C25 . C24 . H241 . 119.3 no
C24 . C25 . C26 . 120.95(15) yes
C24 . C25 . H251 . 119.3 no
C26 . C25 . H251 . 119.7 no
C16 . C26 . C25 . 120.39(15) yes
C16 . C26 . H261 . 119.1 no
C25 . C26 . H261 . 120.5 no
N15 . C30 . C31 . 118.89(14) yes
N15 . C30 . C35 . 119.57(14) yes
C31 . C30 . C35 . 121.45(14) yes
C30 . C31 . C32 . 118.28(15) yes
C30 . C31 . C46 . 121.02(14) yes
C32 . C31 . C46 . 120.70(15) yes
C31 . C32 . C33 . 121.70(16) yes
C31 . C32 . H321 . 119.6 no
C33 . C32 . H321 . 118.7 no
C32 . C33 . C34 . 118.54(15) yes
C32 . C33 . C41 . 119.97(16) yes
C34 . C33 . C41 . 121.49(16) yes
C33 . C34 . C35 . 121.87(15) yes
C33 . C34 . H341 . 119.0 no
C35 . C34 . H341 . 119.1 no
C34 . C35 . C30 . 118.16(15) yes
C34 . C35 . C36 . 121.14(15) yes
C30 . C35 . C36 . 120.70(14) yes
C35 . C36 . H361 . 111.3 no
C35 . C36 . H362 . 111.0 no
H361 . C36 . H362 . 109.0 no
C35 . C36 . H363 . 110.3 no
H361 . C36 . H363 . 107.9 no
H362 . C36 . H363 . 107.2 no
C33 . C41 . H412 . 110.8 no
C33 . C41 . H413 . 109.1 no
H412 . C41 . H413 . 109.3 no
C33 . C41 . H411 . 110.6 no
H412 . C41 . H411 . 108.2 no
H413 . C41 . H411 . 108.7 no
C31 . C46 . H462 . 110.8 no
C31 . C46 . H463 . 108.5 no
H462 . C46 . H463 . 108.8 no
C31 . C46 . H461 . 110.4 no
H462 . C46 . H461 . 109.8 no
H463 . C46 . H461 . 108.6 no
C14 . C50 . C51 . 120.02(14) yes
C14 . C50 . H501 . 119.5 no
C51 . C50 . H501 . 120.5 no
C50 . C51 . C52 . 121.68(15) yes
C50 . C51 . H511 . 120.0 no
C52 . C51 . H511 . 118.3 no
C12 . C52 . C51 . 118.46(15) yes
C12 . C52 . H521 . 120.5 no
C51 . C52 . H521 . 121.0 no
N11 . C56 . C57 . 113.90(13) yes
N11 . C56 . H561 . 110.9 no
C57 . C56 . H561 . 109.4 no
N11 . C56 . H562 . 106.8 no
C57 . C56 . H562 . 107.9 no
H561 . C56 . H562 . 107.7 no
C56 . C57 . C58 . 113.88(14) yes
C56 . C57 . H572 . 110.9 no
C58 . C57 . H572 . 108.7 no
C56 . C57 . H571 . 108.2 no
C58 . C57 . H571 . 107.1 no
H572 . C57 . H571 . 107.8 no
C57 . C58 . H581 . 109.7 no
C57 . C58 . H583 . 110.4 no
H581 . C58 . H583 . 108.2 no
C57 . C58 . H582 . 110.2 no
H581 . C58 . H582 . 110.4 no
H583 . C58 . H582 . 107.8 no
C10 . C66 . C67 . 118.96(15) yes
C10 . C66 . H661 . 121.8 no
C67 . C66 . H661 . 119.2 no
C66 . C67 . C68 . 121.38(14) yes
C66 . C67 . H671 . 118.4 no
C68 . C67 . H671 . 120.2 no
C67 . C68 . C69 . 119.79(15) yes
C67 . C68 . H681 . 120.3 no
C69 . C68 . H681 . 119.9 no
C9 . C69 . C68 . 120.18(15) yes
C9 . C69 . O70 . 117.85(13) yes
C68 . C69 . O70 . 121.95(14) yes
C69 . O70 . C71 . 117.82(13) yes
O70 . C71 . H713 . 106.7 no
O70 . C71 . H712 . 109.7 no
H713 . C71 . H712 . 110.6 no
O70 . C71 . H711 . 112.0 no
H713 . C71 . H711 . 108.4 no
H712 . C71 . H711 . 109.3 no
C7 . C78 . C79 . 120.71(14) yes
C7 . C78 . H781 . 119.7 no
C79 . C78 . H781 . 119.6 no
C78 . C79 . C80 . 120.89(14) yes
C78 . C79 . C82 . 120.56(15) yes
C80 . C79 . C82 . 118.53(14) yes
C79 . C80 . C5 . 118.43(14) yes
C79 . C80 . H801 . 119.6 no
C5 . C80 . H801 . 121.9 no
C79 . C82 . F83 . 113.72(14) yes
C79 . C82 . F85 . 111.91(15) yes
F83 . C82 . F85 . 105.51(16) yes
C79 . C82 . F87 . 112.33(15) yes
F83 . C82 . F87 . 107.42(18) yes
F85 . C82 . F87 . 105.35(18) yes