#------------------------------------------------------------------------------
#$Date: 2020-05-04 05:36:22 +0300 (Mon, 04 May 2020) $
#$Revision: 251457 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/46/4134683.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4134683
loop_
_publ_author_name
'Xie, Weilong'
'Heo, Joon'
'Kim, Dongwook'
'Chang, Sukbok'
_publ_section_title
;
 Copper-Catalyzed Direct C-H Alkylation of Polyfluoroarenes by Using
 Hydrocarbons as an Alkylating Source.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7487
_journal_page_last               7496
_journal_paper_doi               10.1021/jacs.0c00169
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_sum            'C36 H38 F4 O5'
_chemical_formula_weight         626.66
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.609(4)
_cell_length_b                   15.344(6)
_cell_length_c                   21.494(9)
_cell_measurement_reflns_used    9147
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      26.31
_cell_measurement_theta_min      3.14
_cell_volume                     3169(2)
_computing_cell_refinement       'Bruker APEXIII'
_computing_data_collection       'Bruker APEXIII'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP
_computing_publication_material  CIFTAB
_computing_structure_refinement  SHELXL
_computing_structure_solution    SHELXS
_diffrn_ambient_temperature      153(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1391
_diffrn_reflns_av_unetI/netI     0.0878
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            43714
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         2.844
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7250
_exptl_absorpt_correction_T_min  0.6652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.162
_exptl_crystal_size_mid          0.068
_exptl_crystal_size_min          0.067
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details
;
 Flack x determined using 1063 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 _refine_ls_abs_structure_Flack    0.2(6)
;
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.192
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     467
_refine_ls_number_reflns         5583
_refine_ls_number_restraints     522
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.1517
_refine_ls_R_factor_gt           0.1053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0437P)²+5.4612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1829
_refine_ls_wR_factor_ref         0.2036
_reflns_Friedel_coverage         0.771
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3852
_reflns_number_total             5583
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Prod-40.cif
_cod_data_source_block           A19105_019
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 4134682--4134685.cif.
;
_cod_database_code               4134683
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.984
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
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_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1866(10) 0.3869(5) 0.5064(4) 0.040(2) Uani 1 1 d . . . . .
C2 C 0.3124(10) 0.3800(6) 0.4768(4) 0.046(2) Uani 1 1 d . . . . .
C3 C 0.3263(10) 0.3399(6) 0.4184(4) 0.047(2) Uani 1 1 d . . . . .
C4 C 0.2107(11) 0.3091(5) 0.3887(3) 0.043(2) Uani 1 1 d D . . . .
C5 C 0.0819(11) 0.3160(5) 0.4169(4) 0.044(2) Uani 1 1 d . . . . .
C6 C 0.0745(10) 0.3539(5) 0.4751(5) 0.046(2) Uani 1 1 d . . . . .
F7 F 0.4287(6) 0.4102(4) 0.5031(3) 0.078(2) Uani 1 1 d . . . . .
F8 F 0.4510(7) 0.3344(5) 0.3911(3) 0.089(2) Uani 1 1 d . . . . .
F9 F -0.0311(7) 0.2865(4) 0.3887(3) 0.0809(19) Uani 1 1 d . . . . .
F10 F -0.0543(6) 0.3562(4) 0.5015(3) 0.0732(18) Uani 1 1 d . . . . .
O11 O 0.225(3) 0.2763(9) 0.3293(4) 0.063(4) Uani 0.78(2) 1 d D . P A 1
C13 C 0.2521(11) 0.1258(4) 0.3669(4) 0.040(3) Uani 0.78(2) 1 d G . P A 1
H13 H 0.206483 0.138967 0.405012 0.049 Uiso 0.78(2) 1 calc R U P A 1
C12 C 0.2657(11) 0.1895(5) 0.3214(5) 0.041(2) Uani 0.78(2) 1 d DG U P A 1
C21 C 0.3324(11) 0.1702(5) 0.2657(4) 0.046(2) Uani 0.78(2) 1 d G U P A 1
H21 H 0.341691 0.213748 0.234563 0.056 Uiso 0.78(2) 1 calc R U P A 1
C20 C 0.3856(10) 0.0871(6) 0.2556(4) 0.044(2) Uani 0.78(2) 1 d G U P A 1
H20 H 0.431199 0.073948 0.217497 0.053 Uiso 0.78(2) 1 calc R U P A 1
C19 C 0.3720(6) 0.0234(4) 0.3011(4) 0.040(2) Uani 0.78(2) 1 d G U P A 1
C14 C 0.3053(7) 0.0427(4) 0.3568(3) 0.040(2) Uani 0.78(2) 1 d G U P A 1
C15 C 0.2917(11) -0.0210(4) 0.4024(4) 0.049(3) Uani 0.78(2) 1 d G U P A 1
H15 H 0.246077 -0.007807 0.440431 0.059 Uiso 0.78(2) 1 calc R U P A 1
C16 C 0.3449(11) -0.1041(4) 0.3922(5) 0.052(3) Uani 0.78(2) 1 d G U P A 1
H16 H 0.335584 -0.147609 0.423367 0.063 Uiso 0.78(2) 1 calc R U P A 1
C17 C 0.4116(9) -0.1234(4) 0.3365(6) 0.052(3) Uani 0.78(2) 1 d G U P A 1
H17 H 0.447942 -0.180122 0.329611 0.063 Uiso 0.78(2) 1 calc R U P A 1
C18 C 0.4252(8) -0.0596(5) 0.2910(5) 0.047(3) Uani 0.78(2) 1 d G U P A 1
H18 H 0.470795 -0.072835 0.252918 0.056 Uiso 0.78(2) 1 calc R U P A 1
O11B O 0.203(7) 0.284(3) 0.3265(10) 0.040(5) Uani 0.22(2) 1 d D U P A 2
C12B C 0.280(4) 0.1352(16) 0.3625(15) 0.040(4) Uani 0.22(2) 1 d G U P A 2
H12B H 0.250858 0.143512 0.404353 0.047 Uiso 0.22(2) 1 calc R U P A 2
C13B C 0.271(4) 0.2034(16) 0.3202(18) 0.041(4) Uani 0.22(2) 1 d DG U P A 2
C14B C 0.313(4) 0.1912(18) 0.2589(16) 0.041(3) Uani 0.22(2) 1 d G U P A 2
H14B H 0.306934 0.237861 0.230022 0.050 Uiso 0.22(2) 1 calc R U P A 2
C15B C 0.364(4) 0.1107(19) 0.2400(13) 0.041(4) Uani 0.22(2) 1 d G U P A 2
H15B H 0.393162 0.102382 0.198200 0.050 Uiso 0.22(2) 1 calc R U P A 2
C16B C 0.373(2) 0.0425(15) 0.2824(12) 0.043(3) Uani 0.22(2) 1 d G U P A 2
C17B C 0.331(3) 0.0547(14) 0.3436(12) 0.044(3) Uani 0.22(2) 1 d G U P A 2
C18B C 0.340(4) -0.0136(17) 0.3859(13) 0.048(3) Uani 0.22(2) 1 d G U P A 2
H18B H 0.311033 -0.005224 0.427777 0.058 Uiso 0.22(2) 1 calc R U P A 2
C19B C 0.391(4) -0.0941(15) 0.3670(16) 0.051(3) Uani 0.22(2) 1 d G U P A 2
H19B H 0.397260 -0.140705 0.395958 0.061 Uiso 0.22(2) 1 calc R U P A 2
C20B C 0.433(3) -0.1063(15) 0.3058(18) 0.049(4) Uani 0.22(2) 1 d G U P A 2
H20B H 0.468413 -0.161274 0.292883 0.058 Uiso 0.22(2) 1 calc R U P A 2
C21B C 0.424(3) -0.0380(17) 0.2635(15) 0.046(4) Uani 0.22(2) 1 d G U P A 2
H21B H 0.453340 -0.046362 0.221626 0.055 Uiso 0.22(2) 1 calc R U P A 2
C22 C 0.1710(10) 0.4306(5) 0.5696(4) 0.038(2) Uani 1 1 d . . . . .
H22 H 0.069353 0.430616 0.579591 0.046 Uiso 1 1 calc R U . . .
C23 C 0.2172(9) 0.5273(5) 0.5675(4) 0.034(2) Uani 1 1 d . . . . .
C24 C 0.1538(10) 0.5796(5) 0.5235(4) 0.039(2) Uani 1 1 d . . . . .
H24 H 0.091310 0.554343 0.494328 0.047 Uiso 1 1 calc R U . . .
C25 C 0.1802(9) 0.6689(5) 0.5212(4) 0.039(2) Uani 1 1 d . . . . .
C26 C 0.2690(10) 0.7046(6) 0.5640(4) 0.053(3) Uani 1 1 d . . . . .
H26 H 0.285996 0.765588 0.563932 0.064 Uiso 1 1 calc R U . . .
C27 C 0.3336(10) 0.6517(6) 0.6071(4) 0.054(3) Uani 1 1 d . . . . .
H27 H 0.396812 0.677604 0.635666 0.065 Uiso 1 1 calc R U . . .
C28 C 0.3105(9) 0.5619(5) 0.6109(4) 0.037(2) Uani 1 1 d . . . . .
C29 C 0.3792(9) 0.5051(5) 0.6589(4) 0.039(2) Uani 1 1 d . . . . .
H29 H 0.460608 0.476935 0.638036 0.047 Uiso 1 1 calc R U . . .
C30 C 0.4374(11) 0.5557(6) 0.7157(5) 0.060(3) Uani 1 1 d . . . . .
H30A H 0.510648 0.596222 0.701172 0.072 Uiso 1 1 calc R U . . .
H30B H 0.361641 0.591024 0.734043 0.072 Uiso 1 1 calc R U . . .
C31 C 0.4979(10) 0.4973(6) 0.7658(4) 0.049(2) Uani 1 1 d . . . . .
H31A H 0.583907 0.469628 0.749941 0.059 Uiso 1 1 calc R U . . .
H31B H 0.523076 0.533236 0.802356 0.059 Uiso 1 1 calc R U . . .
C32 C 0.3964(8) 0.4272(5) 0.7856(4) 0.0325(19) Uani 1 1 d . . . . .
C33 C 0.4578(9) 0.3515(5) 0.8227(4) 0.041(2) Uani 1 1 d . . . . .
H33 H 0.545707 0.330910 0.802663 0.049 Uiso 1 1 calc R U . . .
C34 C 0.3449(11) 0.2800(6) 0.8180(4) 0.054(3) Uani 1 1 d . . . . .
H34A H 0.275980 0.286013 0.851947 0.065 Uiso 1 1 calc R U . . .
H34B H 0.387137 0.221288 0.820171 0.065 Uiso 1 1 calc R U . . .
C35 C 0.2753(10) 0.2951(5) 0.7537(4) 0.042(2) Uani 1 1 d . . . . .
H35A H 0.288276 0.243854 0.726326 0.050 Uiso 1 1 calc R U . . .
H35B H 0.174449 0.306511 0.758432 0.050 Uiso 1 1 calc R U . . .
C36 C 0.3508(8) 0.3753(5) 0.7274(4) 0.0328(19) Uani 1 1 d . . . . .
H36 H 0.438223 0.353096 0.707789 0.039 Uiso 1 1 calc R U . . .
C37 C 0.2794(8) 0.4309(5) 0.6782(4) 0.0307(18) Uani 1 1 d . . . . .
H37 H 0.192438 0.456541 0.696067 0.037 Uiso 1 1 calc R U . . .
C38 C 0.2431(10) 0.3779(5) 0.6210(3) 0.041(2) Uani 1 1 d . . . . .
H38A H 0.181370 0.329267 0.633539 0.049 Uiso 1 1 calc R U . . .
H38B H 0.329563 0.352145 0.603962 0.049 Uiso 1 1 calc R U . . .
O39 O 0.1186(8) 0.7224(4) 0.4791(3) 0.0560(19) Uani 1 1 d . . . . .
H39 H 0.087749 0.692662 0.449291 0.084 Uiso 1 1 calc R U . . .
O40 O 0.4827(7) 0.3711(4) 0.8869(3) 0.0498(18) Uani 1 1 d . . . . .
H40 H 0.562(11) 0.380(7) 0.892(5) 0.075 Uiso 1 1 d . U . . .
C41 C 0.2699(10) 0.4684(6) 0.8195(4) 0.047(2) Uani 1 1 d . . . . .
H41A H 0.195752 0.424877 0.823531 0.071 Uiso 1 1 calc R U . . .
H41B H 0.235559 0.518242 0.795519 0.071 Uiso 1 1 calc R U . . .
H41C H 0.298446 0.488022 0.861000 0.071 Uiso 1 1 calc R U . . .
O1M O 0.7129(11) 0.4610(6) 0.9117(5) 0.114(3) Uani 1 1 d . U . . .
H1M H 0.779933 0.426410 0.916340 0.172 Uiso 1 1 calc R U . . .
C2M C 0.7636(15) 0.5439(8) 0.8987(6) 0.097(4) Uani 1 1 d . U . . .
H2MA H 0.762308 0.579185 0.936660 0.145 Uiso 1 1 calc R U . . .
H2MB H 0.704916 0.571388 0.866988 0.145 Uiso 1 1 calc R U . . .
H2MC H 0.859245 0.539410 0.883188 0.145 Uiso 1 1 calc R U . . .
O3M O 0.9127(10) 0.3911(5) 0.9769(4) 0.086(2) Uani 1 1 d D U . . .
H3M H 0.914999 0.351984 1.004186 0.129 Uiso 1 1 calc R U . . .
C4M C 1.0183(14) 0.3789(10) 0.9362(6) 0.108(5) Uani 1 1 d D U . . .
H4M1 H 1.020872 0.427490 0.906588 0.163 Uiso 1 1 calc R U . . .
H4M2 H 1.003951 0.324193 0.913571 0.163 Uiso 1 1 calc R U . . .
H4M3 H 1.106639 0.376264 0.958896 0.163 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.0(8) . . ?
C6 C1 C22 121.7(9) . . ?
C2 C1 C22 122.3(8) . . ?
F7 C2 C1 121.1(7) . . ?
F7 C2 C3 116.8(9) . . ?
C1 C2 C3 122.1(8) . . ?
F8 C3 C4 120.3(8) . . ?
F8 C3 C2 120.3(9) . . ?
C4 C3 C2 119.4(9) . . ?
C3 C4 O11 118.6(13) . . ?
C3 C4 C5 119.9(7) . . ?
O11 C4 C5 121.5(13) . . ?
C3 C4 O11B 126(3) . . ?
C5 C4 O11B 113(3) . . ?
F9 C5 C6 121.1(9) . . ?
F9 C5 C4 120.5(8) . . ?
C6 C5 C4 118.4(8) . . ?
F10 C6 C1 120.0(9) . . ?
F10 C6 C5 115.8(8) . . ?
C1 C6 C5 124.1(9) . . ?
C4 O11 C12 119.2(9) . . ?
C12 C13 C14 120.0 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C21 C12 C13 120.0 . . ?
C21 C12 O11 115.9(8) . . ?
C13 C12 O11 123.9(8) . . ?
C12 C21 C20 120.0 . . ?
C12 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C19 C20 C21 120.0 . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C14 C19 C20 120.0 . . ?
C14 C19 C18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C14 C15 120.0 . . ?
C19 C14 C13 120.0 . . ?
C15 C14 C13 120.0 . . ?
C16 C15 C14 120.0 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.0 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 120.0 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C4 O11B C13B 108(2) . . ?
C13B C12B C17B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C17B C12B H12B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B O11B 110(2) . . ?
C12B C13B O11B 129(3) . . ?
C15B C14B C13B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C14B C15B C16B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B C17B 120.0 . . ?
C15B C16B C21B 120.0 . . ?
C17B C16B C21B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B C12B 120.0 . . ?
C16B C17B C12B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C18B C19B C20B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C20B C19B H19B 120.0 . . ?
C21B C20B C19B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C19B C20B H20B 120.0 . . ?
C20B C21B C16B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C16B C21B H21B 120.0 . . ?
C1 C22 C38 111.4(7) . . ?
C1 C22 C23 111.6(6) . . ?
C38 C22 C23 113.4(7) . . ?
C1 C22 H22 106.7 . . ?
C38 C22 H22 106.7 . . ?
C23 C22 H22 106.7 . . ?
C24 C23 C28 121.3(7) . . ?
C24 C23 C22 116.7(7) . . ?
C28 C23 C22 121.9(7) . . ?
C23 C24 C25 120.9(8) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 H24 119.5 . . ?
O39 C25 C26 118.5(7) . . ?
O39 C25 C24 122.5(8) . . ?
C26 C25 C24 118.9(8) . . ?
C25 C26 C27 119.8(8) . . ?
C25 C26 H26 120.1 . . ?
C27 C26 H26 120.1 . . ?
C26 C27 C28 123.1(8) . . ?
C26 C27 H27 118.4 . . ?
C28 C27 H27 118.4 . . ?
C23 C28 C27 116.0(8) . . ?
C23 C28 C29 121.3(7) . . ?
C27 C28 C29 122.8(8) . . ?
C28 C29 C37 109.8(7) . . ?
C28 C29 C30 114.2(7) . . ?
C37 C29 C30 112.4(7) . . ?
C28 C29 H29 106.7 . . ?
C37 C29 H29 106.7 . . ?
C30 C29 H29 106.7 . . ?
C31 C30 C29 113.7(8) . . ?
C31 C30 H30A 108.8 . . ?
C29 C30 H30A 108.8 . . ?
C31 C30 H30B 108.8 . . ?
C29 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C32 C31 C30 111.9(7) . . ?
C32 C31 H31A 109.2 . . ?
C30 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
C30 C31 H31B 109.2 . . ?
H31A C31 H31B 107.9 . . ?
C31 C32 C33 116.0(7) . . ?
C31 C32 C36 108.7(7) . . ?
C33 C32 C36 98.1(6) . . ?
C31 C32 C41 110.4(7) . . ?
C33 C32 C41 111.5(7) . . ?
C36 C32 C41 111.6(7) . . ?
O40 C33 C32 114.0(7) . . ?
O40 C33 C34 109.3(7) . . ?
C32 C33 C34 103.5(7) . . ?
O40 C33 H33 109.9 . . ?
C32 C33 H33 109.9 . . ?
C34 C33 H33 109.9 . . ?
C33 C34 C35 104.8(7) . . ?
C33 C34 H34A 110.8 . . ?
C35 C34 H34A 110.8 . . ?
C33 C34 H34B 110.8 . . ?
C35 C34 H34B 110.8 . . ?
H34A C34 H34B 108.9 . . ?
C36 C35 C34 104.1(7) . . ?
C36 C35 H35A 110.9 . . ?
C34 C35 H35A 110.9 . . ?
C36 C35 H35B 110.9 . . ?
C34 C35 H35B 110.9 . . ?
H35A C35 H35B 109.0 . . ?
C37 C36 C35 119.5(7) . . ?
C37 C36 C32 113.7(6) . . ?
C35 C36 C32 104.4(6) . . ?
C37 C36 H36 106.1 . . ?
C35 C36 H36 106.1 . . ?
C32 C36 H36 106.1 . . ?
C38 C37 C36 111.5(6) . . ?
C38 C37 C29 108.7(6) . . ?
C36 C37 C29 108.6(6) . . ?
C38 C37 H37 109.3 . . ?
C36 C37 H37 109.3 . . ?
C29 C37 H37 109.3 . . ?
C37 C38 C22 113.9(6) . . ?
C37 C38 H38A 108.8 . . ?
C22 C38 H38A 108.8 . . ?
C37 C38 H38B 108.8 . . ?
C22 C38 H38B 108.8 . . ?
H38A C38 H38B 107.7 . . ?
C25 O39 H39 109.5 . . ?
C33 O40 H40 110(9) . . ?
C32 C41 H41A 109.5 . . ?
C32 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C32 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C2M O1M H1M 109.5 . . ?
O1M C2M H2MA 109.5 . . ?
O1M C2M H2MB 109.5 . . ?
H2MA C2M H2MB 109.5 . . ?
O1M C2M H2MC 109.5 . . ?
H2MA C2M H2MC 109.5 . . ?
H2MB C2M H2MC 109.5 . . ?
C4M O3M H3M 109.5 . . ?
O3M C4M H4M1 109.5 . . ?
O3M C4M H4M2 109.5 . . ?
H4M1 C4M H4M2 109.5 . . ?
O3M C4M H4M3 109.5 . . ?
H4M1 C4M H4M3 109.5 . . ?
H4M2 C4M H4M3 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.367(12) . ?
C1 C2 1.370(13) . ?
C1 C22 1.523(11) . ?
C2 F7 1.335(10) . ?
C2 C3 1.406(12) . ?
C3 F8 1.337(11) . ?
C3 C4 1.365(12) . ?
C4 O11 1.380(10) . ?
C4 C5 1.382(13) . ?
C4 O11B 1.394(14) . ?
C5 F9 1.323(10) . ?
C5 C6 1.380(12) . ?
C6 F10 1.362(11) . ?
O11 C12 1.399(9) . ?
C13 C12 1.3900 . ?
C13 C14 1.3900 . ?
C13 H13 0.9500 . ?
C12 C21 1.3900 . ?
C21 C20 1.3900 . ?
C21 H21 0.9500 . ?
C20 C19 1.3900 . ?
C20 H20 0.9500 . ?
C19 C14 1.3900 . ?
C19 C18 1.3900 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 H16 0.9500 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
O11B C13B 1.401(14) . ?
C12B C13B 1.3900 . ?
C12B C17B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B C17B 1.3900 . ?
C16B C21B 1.3900 . ?
C17B C18B 1.3900 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B C20B 1.3900 . ?
C19B H19B 0.9500 . ?
C20B C21B 1.3900 . ?
C20B H20B 0.9500 . ?
C21B H21B 0.9500 . ?
C22 C38 1.535(11) . ?
C22 C23 1.549(11) . ?
C22 H22 1.0000 . ?
C23 C24 1.383(11) . ?
C23 C28 1.398(11) . ?
C24 C25 1.394(11) . ?
C24 H24 0.9500 . ?
C25 O39 1.358(10) . ?
C25 C26 1.368(12) . ?
C26 C27 1.380(12) . ?
C26 H26 0.9500 . ?
C27 C28 1.398(11) . ?
C27 H27 0.9500 . ?
C28 C29 1.503(11) . ?
C29 C37 1.546(10) . ?
C29 C30 1.551(12) . ?
C29 H29 1.0000 . ?
C30 C31 1.516(12) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.513(11) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 C33 1.529(11) . ?
C32 C36 1.547(11) . ?
C32 C41 1.552(12) . ?
C33 O40 1.431(10) . ?
C33 C34 1.545(13) . ?
C33 H33 1.0000 . ?
C34 C35 1.551(12) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C35 C36 1.537(11) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 C37 1.521(11) . ?
C36 H36 1.0000 . ?
C37 C38 1.514(10) . ?
C37 H37 1.0000 . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
O39 H39 0.8400 . ?
O40 H40 0.79(11) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
O1M C2M 1.390(13) . ?
O1M H1M 0.8400 . ?
C2M H2MA 0.9800 . ?
C2M H2MB 0.9800 . ?
C2M H2MC 0.9800 . ?
O3M C4M 1.353(13) . ?
O3M H3M 0.8400 . ?
C4M H4M1 0.9800 . ?
C4M H4M2 0.9800 . ?
C4M H4M3 0.9800 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O39 H39 O40 0.84 1.79 2.633(8) 178.4 2_564 yes
O40 H40 O1M 0.79(11) 1.95(11) 2.661(11) 150(12) . yes
O1M H1M O3M 0.84 1.90 2.606(13) 140.8 . yes
O3M H3M O39 0.84 2.05 2.773(9) 144.4 3_646 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F7 179.9(8) . . . . ?
C22 C1 C2 F7 1.4(13) . . . . ?
C6 C1 C2 C3 -1.3(13) . . . . ?
C22 C1 C2 C3 -179.8(8) . . . . ?
F7 C2 C3 F8 -1.0(13) . . . . ?
C1 C2 C3 F8 -179.9(9) . . . . ?
F7 C2 C3 C4 -178.8(8) . . . . ?
C1 C2 C3 C4 2.3(14) . . . . ?
F8 C3 C4 O11 -2.9(13) . . . . ?
C2 C3 C4 O11 174.8(9) . . . . ?
F8 C3 C4 C5 -179.2(8) . . . . ?
C2 C3 C4 C5 -1.4(13) . . . . ?
F8 C3 C4 O11B -11(2) . . . . ?
C2 C3 C4 O11B 166.5(17) . . . . ?
C3 C4 C5 F9 180.0(8) . . . . ?
O11 C4 C5 F9 3.9(14) . . . . ?
O11B C4 C5 F9 11(2) . . . . ?
C3 C4 C5 C6 -0.3(12) . . . . ?
O11 C4 C5 C6 -176.5(9) . . . . ?
O11B C4 C5 C6 -169.7(19) . . . . ?
C2 C1 C6 F10 178.6(8) . . . . ?
C22 C1 C6 F10 -2.9(12) . . . . ?
C2 C1 C6 C5 -0.6(13) . . . . ?
C22 C1 C6 C5 177.9(8) . . . . ?
F9 C5 C6 F10 1.8(12) . . . . ?
C4 C5 C6 F10 -177.8(7) . . . . ?
F9 C5 C6 C1 -179.0(8) . . . . ?
C4 C5 C6 C1 1.4(13) . . . . ?
C3 C4 O11 C12 84(2) . . . . ?
C5 C4 O11 C12 -99.5(19) . . . . ?
C14 C13 C12 C21 0.0 . . . . ?
C14 C13 C12 O11 -175.0(14) . . . . ?
C4 O11 C12 C21 -154.3(15) . . . . ?
C4 O11 C12 C13 21(3) . . . . ?
C13 C12 C21 C20 0.0 . . . . ?
O11 C12 C21 C20 175.4(13) . . . . ?
C12 C21 C20 C19 0.0 . . . . ?
C21 C20 C19 C14 0.0 . . . . ?
C21 C20 C19 C18 180.0 . . . . ?
C20 C19 C14 C15 180.0 . . . . ?
C18 C19 C14 C15 0.0 . . . . ?
C20 C19 C14 C13 0.0 . . . . ?
C18 C19 C14 C13 180.0 . . . . ?
C12 C13 C14 C19 0.0 . . . . ?
C12 C13 C14 C15 180.0 . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
C14 C19 C18 C17 0.0 . . . . ?
C20 C19 C18 C17 180.0 . . . . ?
C3 C4 O11B C13B 74(5) . . . . ?
C5 C4 O11B C13B -117(4) . . . . ?
C17B C12B C13B C14B 0.0 . . . . ?
C17B C12B C13B O11B 169(5) . . . . ?
C4 O11B C13B C14B -157(3) . . . . ?
C4 O11B C13B C12B 33(7) . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
O11B C13B C14B C15B -171(4) . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
C14B C15B C16B C17B 0.0 . . . . ?
C14B C15B C16B C21B 180.0 . . . . ?
C15B C16B C17B C18B 180.0 . . . . ?
C21B C16B C17B C18B 0.0 . . . . ?
C15B C16B C17B C12B 0.0 . . . . ?
C21B C16B C17B C12B 180.0 . . . . ?
C13B C12B C17B C18B 180.0 . . . . ?
C13B C12B C17B C16B 0.0 . . . . ?
C16B C17B C18B C19B 0.0 . . . . ?
C12B C17B C18B C19B 180.0 . . . . ?
C17B C18B C19B C20B 0.0 . . . . ?
C18B C19B C20B C21B 0.0 . . . . ?
C19B C20B C21B C16B 0.0 . . . . ?
C15B C16B C21B C20B 180.0 . . . . ?
C17B C16B C21B C20B 0.0 . . . . ?
C6 C1 C22 C38 114.0(9) . . . . ?
C2 C1 C22 C38 -67.6(10) . . . . ?
C6 C1 C22 C23 -118.1(9) . . . . ?
C2 C1 C22 C23 60.3(11) . . . . ?
C1 C22 C23 C24 54.9(10) . . . . ?
C38 C22 C23 C24 -178.3(7) . . . . ?
C1 C22 C23 C28 -129.8(8) . . . . ?
C38 C22 C23 C28 -3.0(11) . . . . ?
C28 C23 C24 C25 -0.5(13) . . . . ?
C22 C23 C24 C25 174.9(8) . . . . ?
C23 C24 C25 O39 -179.2(8) . . . . ?
C23 C24 C25 C26 -0.9(13) . . . . ?
O39 C25 C26 C27 -179.7(9) . . . . ?
C24 C25 C26 C27 2.0(14) . . . . ?
C25 C26 C27 C28 -1.7(16) . . . . ?
C24 C23 C28 C27 0.7(12) . . . . ?
C22 C23 C28 C27 -174.4(8) . . . . ?
C24 C23 C28 C29 179.8(8) . . . . ?
C22 C23 C28 C29 4.7(12) . . . . ?
C26 C27 C28 C23 0.4(14) . . . . ?
C26 C27 C28 C29 -178.7(9) . . . . ?
C23 C28 C29 C37 -33.0(10) . . . . ?
C27 C28 C29 C37 146.1(8) . . . . ?
C23 C28 C29 C30 -160.2(8) . . . . ?
C27 C28 C29 C30 18.9(12) . . . . ?
C28 C29 C30 C31 176.2(8) . . . . ?
C37 C29 C30 C31 50.3(11) . . . . ?
C29 C30 C31 C32 -52.6(12) . . . . ?
C30 C31 C32 C33 164.7(8) . . . . ?
C30 C31 C32 C36 55.4(10) . . . . ?
C30 C31 C32 C41 -67.3(10) . . . . ?
C31 C32 C33 O40 78.4(10) . . . . ?
C36 C32 C33 O40 -166.2(7) . . . . ?
C41 C32 C33 O40 -49.1(10) . . . . ?
C31 C32 C33 C34 -163.0(8) . . . . ?
C36 C32 C33 C34 -47.5(7) . . . . ?
C41 C32 C33 C34 69.6(8) . . . . ?
O40 C33 C34 C35 153.1(7) . . . . ?
C32 C33 C34 C35 31.2(9) . . . . ?
C33 C34 C35 C36 -1.5(9) . . . . ?
C34 C35 C36 C37 -156.8(7) . . . . ?
C34 C35 C36 C32 -28.4(8) . . . . ?
C31 C32 C36 C37 -60.1(9) . . . . ?
C33 C32 C36 C37 178.8(7) . . . . ?
C41 C32 C36 C37 61.8(9) . . . . ?
C31 C32 C36 C35 168.0(7) . . . . ?
C33 C32 C36 C35 47.0(7) . . . . ?
C41 C32 C36 C35 -70.0(8) . . . . ?
C35 C36 C37 C38 -58.8(9) . . . . ?
C32 C36 C37 C38 177.3(7) . . . . ?
C35 C36 C37 C29 -178.5(7) . . . . ?
C32 C36 C37 C29 57.5(8) . . . . ?
C28 C29 C37 C38 59.3(9) . . . . ?
C30 C29 C37 C38 -172.5(8) . . . . ?
C28 C29 C37 C36 -179.2(7) . . . . ?
C30 C29 C37 C36 -51.0(9) . . . . ?
C36 C37 C38 C22 -179.8(7) . . . . ?
C29 C37 C38 C22 -60.1(9) . . . . ?
C1 C22 C38 C37 158.2(7) . . . . ?
C23 C22 C38 C37 31.3(10) . . . . ?
