#------------------------------------------------------------------------------
#$Date: 2020-06-04 04:08:25 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252610 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134917.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_4134917
loop_
_publ_author_name
'Strassfeld, Daniel A.'
'Wickens, Zachary K.'
'Picazo, Elias'
'Jacobsen, Eric N.'
_publ_section_title
;
 Highly Enantioselective, Hydrogen-Bond-Donor Catalyzed Additions to
 Oxetanes.
;
_journal_issue                   20
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9175
_journal_page_last               9180
_journal_paper_doi               10.1021/jacs.0c03991
_journal_volume                  142
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H24 Br F3 O2 Si'
_chemical_formula_weight         461.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                115.1170(11)
_cell_angle_beta                 96.8758(12)
_cell_angle_gamma                106.1458(11)
_cell_formula_units_Z            2
_cell_length_a                   9.7525(2)
_cell_length_b                   10.9189(2)
_cell_length_c                   11.7345(2)
_cell_measurement_reflns_used    9804
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.0
_cell_measurement_theta_min      2.57
_cell_volume                     1045.39(4)
_computing_cell_refinement       'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_data_reduction        'SAINT 8.37A (Bruker-AXS, 2015)'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2015)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker D8 goniometer with CCD area detector  
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'I\mS microfocus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            41662
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.124
_diffrn_reflns_theta_min         1.993
_exptl_absorpt_coefficient_mu    2.061
_exptl_absorpt_correction_T_max  0.6467
_exptl_absorpt_correction_T_min  0.5783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 4241 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     550
_refine_ls_number_reflns         9165
_refine_ls_number_restraints     310
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0247
_refine_ls_R_factor_gt           0.0234
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0385P)²+0.2223P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0582
_refine_ls_wR_factor_ref         0.0587
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                8882
_reflns_number_total             9165
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c03991_si_004.cif
_cod_data_source_block           DAS-III-249-1
_cod_depositor_comments
'Adding full bibliography for 4134915--4134918.cif.'
_cod_database_code               4134917
_shelx_shelxl_version_number     2014/7
_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   0.683
_shelx_estimated_absorpt_t_max   0.790
loop_
_space_group_symop_operation_xyz
'x, y, 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
Br1 Br 0.32130(3) -0.07511(3) 0.12442(3) 0.02540(8) Uani 1 1 d . . . . .
Si1 Si 0.23071(9) 0.34342(9) 0.52399(8) 0.01812(16) Uani 1 1 d . . . . .
F1 F 1.0061(3) 0.6542(3) 0.9051(2) 0.0603(8) Uani 1 1 d . . . . .
F2 F 0.9487(3) 0.7691(2) 0.8133(3) 0.0529(7) Uani 1 1 d . . . . .
F3 F 1.1015(2) 0.6695(3) 0.7542(3) 0.0599(8) Uani 1 1 d . . . . .
O1 O 0.4980(2) 0.0050(2) 0.4088(2) 0.0174(4) Uani 1 1 d . . . . .
O2 O 0.3054(2) 0.2430(2) 0.4187(2) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.7072(3) -0.0509(3) 0.5805(3) 0.0218(6) Uani 1 1 d . . . . .
H1 H 0.7506 0.0522 0.6267 0.026 Uiso 1 1 calc R U . . .
C2 C 0.7107(3) -0.1284(4) 0.6470(3) 0.0259(7) Uani 1 1 d . . . . .
H2 H 0.7567 -0.0789 0.7384 0.031 Uiso 1 1 calc R U . . .
C3 C 0.6471(3) -0.2785(4) 0.5802(4) 0.0287(7) Uani 1 1 d . . . . .
H3 H 0.6481 -0.3318 0.6264 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5824(3) -0.3513(4) 0.4471(4) 0.0278(7) Uani 1 1 d . . . . .
H4 H 0.5403 -0.4545 0.4015 0.033 Uiso 1 1 calc R U . . .
C5 C 0.5789(3) -0.2731(3) 0.3797(3) 0.0224(6) Uani 1 1 d . . . . .
H5 H 0.5341 -0.3233 0.2880 0.027 Uiso 1 1 calc R U . . .
C6 C 0.6404(3) -0.1221(3) 0.4456(3) 0.0182(6) Uani 1 1 d . . . . .
C7 C 0.6226(3) -0.0354(3) 0.3782(3) 0.0215(6) Uani 1 1 d . . . . .
H7A H 0.7132 0.0521 0.4107 0.026 Uiso 1 1 calc R U . . .
H7B H 0.6033 -0.0945 0.2825 0.026 Uiso 1 1 calc R U . . .
C8 C 0.4869(3) 0.1260(3) 0.3960(3) 0.0150(5) Uani 1 1 d . . . . .
C9 C 0.6176(3) 0.2644(3) 0.4963(3) 0.0166(5) Uani 1 1 d . . . . .
C10 C 0.6484(3) 0.2938(3) 0.6266(3) 0.0207(6) Uani 1 1 d . . . . .
H10 H 0.5889 0.2281 0.6501 0.025 Uiso 1 1 calc R U . . .
C11 C 0.7643(3) 0.4170(3) 0.7219(3) 0.0219(6) Uani 1 1 d . . . . .
H11 H 0.7838 0.4350 0.8099 0.026 Uiso 1 1 calc R U . . .
C12 C 0.8520(3) 0.5144(3) 0.6897(3) 0.0193(6) Uani 1 1 d . . . . .
C13 C 0.8241(3) 0.4859(3) 0.5599(3) 0.0188(6) Uani 1 1 d . . . . .
H13 H 0.8850 0.5509 0.5365 0.023 Uiso 1 1 calc R U . . .
C14 C 0.7074(3) 0.3624(3) 0.4649(3) 0.0174(5) Uani 1 1 d . . . . .
H14 H 0.6884 0.3444 0.3768 0.021 Uiso 1 1 calc R U . . .
C15 C 0.9775(3) 0.6492(4) 0.7901(3) 0.0241(6) Uani 1 1 d . . . . .
C16 C 0.4770(3) 0.1052(3) 0.2576(3) 0.0180(5) Uani 1 1 d . . . . .
H16A H 0.5735 0.1061 0.2388 0.022 Uiso 1 1 calc R U . . .
H16B H 0.4584 0.1879 0.2531 0.022 Uiso 1 1 calc R U . . .
C17 C 0.3408(3) 0.1311(3) 0.4314(3) 0.0168(5) Uani 1 1 d . . . . .
H17A H 0.2596 0.0364 0.3730 0.020 Uiso 1 1 calc R U . . .
H17B H 0.3508 0.1487 0.5226 0.020 Uiso 1 1 calc R U . . .
C18 C 0.3691(4) 0.4617(4) 0.6865(4) 0.0365(8) Uani 1 1 d . . . . .
H18A H 0.3931 0.4012 0.7220 0.055 Uiso 1 1 calc R U . . .
H18B H 0.3279 0.5267 0.7461 0.055 Uiso 1 1 calc R U . . .
H18C H 0.4595 0.5195 0.6770 0.055 Uiso 1 1 calc R U . . .
C19 C 0.0647(4) 0.2247(4) 0.5399(4) 0.0296(7) Uani 1 1 d . . . . .
H19A H -0.0083 0.1624 0.4542 0.044 Uiso 1 1 calc R U . . .
H19B H 0.0211 0.2850 0.6013 0.044 Uiso 1 1 calc R U . . .
H19C H 0.0938 0.1641 0.5727 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1800(4) 0.4527(4) 0.4537(4) 0.0318(7) Uani 1 1 d . . . . .
H20A H 0.2684 0.5097 0.4413 0.048 Uiso 1 1 calc R U . . .
H20B H 0.1394 0.5185 0.5134 0.048 Uiso 1 1 calc R U . . .
H20C H 0.1053 0.3880 0.3691 0.048 Uiso 1 1 calc R U . . .
Br2 Br -0.32368(3) 0.36398(3) 0.07334(3) 0.02771(8) Uani 1 1 d . . . . .
Si2 Si 0.16333(9) 0.37718(9) 0.04080(8) 0.01841(17) Uani 1 1 d . . . . .
O3 O -0.1398(2) 0.6948(2) 0.19485(19) 0.0161(4) Uani 1 1 d . . . . .
O4 O 0.0806(2) 0.4650(2) 0.14569(19) 0.0177(4) Uani 1 1 d . . . . .
C21 C -0.0894(3) 1.0227(3) 0.1604(3) 0.0224(6) Uani 1 1 d . . . . .
H21 H 0.0063 1.0855 0.2187 0.027 Uiso 1 1 calc R U . . .
C22 C -0.1707(4) 1.0738(4) 0.0980(3) 0.0273(7) Uani 1 1 d . . . . .
H22 H -0.1306 1.1713 0.1140 0.033 Uiso 1 1 calc R U . . .
C23 C -0.3102(4) 0.9829(4) 0.0124(3) 0.0300(7) Uani 1 1 d . . . . .
H23 H -0.3657 1.0177 -0.0304 0.036 Uiso 1 1 calc R U . . .
C24 C -0.3685(4) 0.8407(4) -0.0103(3) 0.0266(7) Uani 1 1 d . . . . .
H24 H -0.4643 0.7783 -0.0686 0.032 Uiso 1 1 calc R U . . .
C25 C -0.2871(3) 0.7890(3) 0.0520(3) 0.0212(6) Uani 1 1 d . . . . .
H25 H -0.3272 0.6913 0.0357 0.025 Uiso 1 1 calc R U . . .
C26 C -0.1472(3) 0.8804(3) 0.1382(3) 0.0169(6) Uani 1 1 d . . . . .
C27 C -0.0539(3) 0.8319(3) 0.2091(3) 0.0205(6) Uani 1 1 d . . . . .
H27A H 0.0319 0.8240 0.1731 0.025 Uiso 1 1 calc R U . . .
H27B H -0.0154 0.9048 0.3031 0.025 Uiso 1 1 calc R U . . .
C28 C -0.0559(3) 0.6220(3) 0.2319(3) 0.0144(5) Uani 1 1 d . . . . .
C29 C 0.0487(3) 0.7226(3) 0.3705(3) 0.0145(5) Uani 1 1 d . . . . .
C30 C -0.0095(3) 0.7952(3) 0.4711(3) 0.0185(6) Uani 1 1 d . . . . .
H30 H -0.1121 0.7803 0.4522 0.022 Uiso 1 1 calc R U . . .
C31 C 0.0797(3) 0.8879(3) 0.5970(3) 0.0196(6) Uani 1 1 d . . . . .
H31 H 0.0388 0.9363 0.6643 0.023 Uiso 1 1 calc R U . . .
C32 C 0.2303(3) 0.9102(3) 0.6251(3) 0.0187(6) Uani 1 1 d . . . . .
C33 C 0.2900(3) 0.8393(3) 0.5264(3) 0.0179(6) Uani 1 1 d . . . . .
H33 H 0.3926 0.8545 0.5457 0.022 Uiso 1 1 calc R U . . .
C34 C 0.1998(3) 0.7466(3) 0.4001(3) 0.0155(5) Uani 1 1 d . . . . .
H34 H 0.2412 0.6988 0.3328 0.019 Uiso 1 1 calc R U . . .
C35 C 0.3276(4) 1.0147(4) 0.7599(3) 0.0298(7) Uani 0.52(2) 1 d D U P A 1
F4 F 0.2709(17) 1.0060(12) 0.8541(10) 0.034(4) Uani 0.52(2) 1 d D U P A 1
F5 F 0.3502(14) 1.1569(7) 0.7853(9) 0.033(2) Uani 0.52(2) 1 d D U P A 1
F6 F 0.4652(12) 1.0175(19) 0.7800(9) 0.055(4) Uani 0.52(2) 1 d D U P A 1
C35A C 0.3276(4) 1.0147(4) 0.7599(3) 0.0298(7) Uani 0.163(19) 1 d D U P A 2
F4A F 0.319(3) 0.979(3) 0.853(2) 0.036(5) Uani 0.163(19) 1 d D U P A 2
F5A F 0.308(3) 1.145(2) 0.807(3) 0.044(6) Uani 0.163(19) 1 d D U P A 2
F6A F 0.477(2) 1.069(4) 0.766(3) 0.042(6) Uani 0.163(19) 1 d D U P A 2
C35B C 0.3276(4) 1.0147(4) 0.7599(3) 0.0298(7) Uani 0.316(15) 1 d D U P A 3
F4B F 0.247(2) 1.032(2) 0.8468(18) 0.031(4) Uani 0.316(15) 1 d D U P A 3
F5B F 0.407(2) 1.1331(18) 0.7772(13) 0.063(5) Uani 0.316(15) 1 d D U P A 3
F6B F 0.4144(18) 0.943(2) 0.7941(10) 0.058(4) Uani 0.316(15) 1 d D U P A 3
C36 C -0.1693(3) 0.4982(3) 0.2377(3) 0.0173(5) Uani 1 1 d . . . . .
H36A H -0.2166 0.5397 0.3074 0.021 Uiso 1 1 calc R U . . .
H36B H -0.1170 0.4432 0.2618 0.021 Uiso 1 1 calc R U . . .
C37 C 0.0237(3) 0.5639(3) 0.1272(3) 0.0170(5) Uani 1 1 d . . . . .
H37A H -0.0466 0.5140 0.0391 0.020 Uiso 1 1 calc R U . . .
H37B H 0.1061 0.6457 0.1334 0.020 Uiso 1 1 calc R U . . .
C38 C 0.3000(4) 0.5083(4) 0.0096(4) 0.0350(8) Uani 1 1 d . . . . .
H38A H 0.2472 0.5362 -0.0461 0.052 Uiso 1 1 calc R U . . .
H38B H 0.3655 0.4628 -0.0345 0.052 Uiso 1 1 calc R U . . .
H38C H 0.3592 0.5949 0.0929 0.052 Uiso 1 1 calc R U . . .
C39 C 0.0200(5) 0.2378(4) -0.1148(3) 0.0384(9) Uani 1 1 d . . . . .
H39A H -0.0445 0.1618 -0.1009 0.058 Uiso 1 1 calc R U . . .
H39B H 0.0685 0.1946 -0.1817 0.058 Uiso 1 1 calc R U . . .
H39C H -0.0395 0.2835 -0.1440 0.058 Uiso 1 1 calc R U . . .
C40 C 0.2551(4) 0.2954(4) 0.1202(3) 0.0274(7) Uani 1 1 d . . . . .
H40A H 0.3142 0.3698 0.2093 0.041 Uiso 1 1 calc R U . . .
H40B H 0.3201 0.2560 0.0699 0.041 Uiso 1 1 calc R U . . .
H40C H 0.1797 0.2169 0.1235 0.041 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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
O2 Si1 C20 105.11(13) . . ?
O2 Si1 C19 110.23(14) . . ?
C20 Si1 C19 111.16(17) . . ?
O2 Si1 C18 109.67(14) . . ?
C20 Si1 C18 111.12(19) . . ?
C19 Si1 C18 109.48(17) . . ?
C8 O1 C7 117.1(2) . . ?
C17 O2 Si1 121.34(18) . . ?
C2 C1 C6 120.9(3) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C1 C2 C3 119.8(3) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 121.3(3) . . ?
C1 C6 C7 119.8(3) . . ?
O1 C7 C6 105.7(2) . . ?
O1 C7 H7A 110.6 . . ?
C6 C7 H7A 110.6 . . ?
O1 C7 H7B 110.6 . . ?
C6 C7 H7B 110.6 . . ?
H7A C7 H7B 108.7 . . ?
O1 C8 C16 113.2(2) . . ?
O1 C8 C9 109.7(2) . . ?
C16 C8 C9 111.0(2) . . ?
O1 C8 C17 101.7(2) . . ?
C16 C8 C17 110.7(2) . . ?
C9 C8 C17 110.3(2) . . ?
C14 C9 C10 118.1(3) . . ?
C14 C9 C8 123.8(3) . . ?
C10 C9 C8 118.1(3) . . ?
C11 C10 C9 121.0(3) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 120.4(3) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.4(3) . . ?
C11 C12 C15 121.9(3) . . ?
C13 C12 C15 118.7(3) . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
F3 C15 F1 108.5(3) . . ?
F3 C15 F2 104.2(3) . . ?
F1 C15 F2 105.0(3) . . ?
F3 C15 C12 113.4(3) . . ?
F1 C15 C12 113.0(3) . . ?
F2 C15 C12 112.0(3) . . ?
C8 C16 Br1 113.01(19) . . ?
C8 C16 H16A 109.0 . . ?
Br1 C16 H16A 109.0 . . ?
C8 C16 H16B 109.0 . . ?
Br1 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C8 110.6(2) . . ?
O2 C17 H17A 109.5 . . ?
C8 C17 H17A 109.5 . . ?
O2 C17 H17B 109.5 . . ?
C8 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
Si1 C18 H18A 109.5 . . ?
Si1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
Si1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
Si1 C19 H19A 109.5 . . ?
Si1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
Si1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
Si1 C20 H20A 109.5 . . ?
Si1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
Si1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O4 Si2 C40 105.62(13) . . ?
O4 Si2 C39 108.54(15) . . ?
C40 Si2 C39 112.24(18) . . ?
O4 Si2 C38 109.27(14) . . ?
C40 Si2 C38 111.61(17) . . ?
C39 Si2 C38 109.41(19) . . ?
C27 O3 C28 115.1(2) . . ?
C37 O4 Si2 120.28(17) . . ?
C22 C21 C26 120.5(3) . . ?
C22 C21 H21 119.8 . . ?
C26 C21 H21 119.8 . . ?
C23 C22 C21 120.1(3) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C22 C23 C24 119.7(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C23 C24 C25 120.3(3) . . ?
C23 C24 H24 119.9 . . ?
C25 C24 H24 119.9 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C21 C26 C25 119.4(3) . . ?
C21 C26 C27 117.9(3) . . ?
C25 C26 C27 122.7(3) . . ?
O3 C27 C26 110.2(2) . . ?
O3 C27 H27A 109.6 . . ?
C26 C27 H27A 109.6 . . ?
O3 C27 H27B 109.6 . . ?
C26 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
O3 C28 C36 105.6(2) . . ?
O3 C28 C29 110.7(2) . . ?
C36 C28 C29 106.7(2) . . ?
O3 C28 C37 108.6(2) . . ?
C36 C28 C37 111.1(2) . . ?
C29 C28 C37 113.8(2) . . ?
C34 C29 C30 118.6(3) . . ?
C34 C29 C28 122.8(2) . . ?
C30 C29 C28 118.6(2) . . ?
C31 C30 C29 121.0(3) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 119.7(3) . . ?
C30 C31 H31 120.2 . . ?
C32 C31 H31 120.2 . . ?
C33 C32 C31 120.1(3) . . ?
C33 C32 C35B 120.3(3) . . ?
C31 C32 C35B 119.6(3) . . ?
C33 C32 C35 120.3(3) . . ?
C31 C32 C35 119.6(3) . . ?
C33 C32 C35A 120.3(3) . . ?
C31 C32 C35A 119.6(3) . . ?
C34 C33 C32 120.0(3) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C29 120.7(3) . . ?
C33 C34 H34 119.7 . . ?
C29 C34 H34 119.7 . . ?
F4 C35 F6 110.4(7) . . ?
F4 C35 F5 103.2(6) . . ?
F6 C35 F5 101.9(7) . . ?
F4 C35 C32 114.8(6) . . ?
F6 C35 C32 115.0(4) . . ?
F5 C35 C32 110.0(4) . . ?
F4A C35A F5A 105.0(14) . . ?
F4A C35A F6A 107.9(14) . . ?
F5A C35A F6A 96.4(14) . . ?
F4A C35A C32 119.5(11) . . ?
F5A C35A C32 111.5(12) . . ?
F6A C35A C32 113.8(11) . . ?
F5B C35B F4B 110.3(12) . . ?
F5B C35B F6B 110.9(10) . . ?
F4B C35B F6B 101.2(9) . . ?
F5B C35B C32 116.4(7) . . ?
F4B C35B C32 110.4(10) . . ?
F6B C35B C32 106.6(5) . . ?
C28 C36 Br2 113.59(19) . . ?
C28 C36 H36A 108.8 . . ?
Br2 C36 H36A 108.8 . . ?
C28 C36 H36B 108.8 . . ?
Br2 C36 H36B 108.8 . . ?
H36A C36 H36B 107.7 . . ?
O4 C37 C28 109.7(2) . . ?
O4 C37 H37A 109.7 . . ?
C28 C37 H37A 109.7 . . ?
O4 C37 H37B 109.7 . . ?
C28 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
Si2 C38 H38A 109.5 . . ?
Si2 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
Si2 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
Si2 C39 H39A 109.5 . . ?
Si2 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
Si2 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
Si2 C40 H40A 109.5 . . ?
Si2 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
Si2 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
Br1 C16 1.944(3) . ?
Si1 O2 1.663(2) . ?
Si1 C20 1.849(3) . ?
Si1 C19 1.856(3) . ?
Si1 C18 1.857(4) . ?
F1 C15 1.319(4) . ?
F2 C15 1.336(4) . ?
F3 C15 1.319(4) . ?
O1 C8 1.422(3) . ?
O1 C7 1.438(3) . ?
O2 C17 1.418(3) . ?
C1 C2 1.376(5) . ?
C1 C6 1.400(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.499(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C16 1.529(4) . ?
C8 C9 1.534(4) . ?
C8 C17 1.540(4) . ?
C9 C14 1.392(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.383(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.394(4) . ?
C12 C15 1.495(4) . ?
C13 C14 1.386(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
Br2 C36 1.953(3) . ?
Si2 O4 1.659(2) . ?
Si2 C40 1.849(3) . ?
Si2 C39 1.858(4) . ?
Si2 C38 1.860(4) . ?
O3 C27 1.424(3) . ?
O3 C28 1.436(3) . ?
O4 C37 1.423(3) . ?
C21 C22 1.389(4) . ?
C21 C26 1.391(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.386(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.388(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.395(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.391(4) . ?
C25 H25 0.9500 . ?
C26 C27 1.504(4) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C36 1.523(4) . ?
C28 C29 1.535(4) . ?
C28 C37 1.536(4) . ?
C29 C34 1.395(4) . ?
C29 C30 1.400(4) . ?
C30 C31 1.377(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.394(4) . ?
C31 H31 0.9500 . ?
C32 C33 1.388(4) . ?
C32 C35B 1.487(4) . ?
C32 C35 1.487(4) . ?
C32 C35A 1.487(4) . ?
C33 C34 1.384(4) . ?
C33 H33 0.9500 . ?
C34 H34 0.9500 . ?
C35 F4 1.320(10) . ?
C35 F6 1.324(8) . ?
C35 F5 1.396(8) . ?
C35A F4A 1.309(18) . ?
C35A F5A 1.375(19) . ?
C35A F6A 1.392(17) . ?
C35B F5B 1.223(13) . ?
C35B F4B 1.343(15) . ?
C35B F6B 1.430(11) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
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
C20 Si1 O2 C17 -171.9(2) . . . . ?
C19 Si1 O2 C17 -52.0(2) . . . . ?
C18 Si1 O2 C17 68.6(3) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C1 C2 C3 C4 1.1(5) . . . . ?
C2 C3 C4 C5 -1.0(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
C4 C5 C6 C7 -172.9(3) . . . . ?
C2 C1 C6 C5 -0.6(4) . . . . ?
C2 C1 C6 C7 173.1(3) . . . . ?
C8 O1 C7 C6 159.2(2) . . . . ?
C5 C6 C7 O1 95.9(3) . . . . ?
C1 C6 C7 O1 -77.6(3) . . . . ?
C7 O1 C8 C16 59.3(3) . . . . ?
C7 O1 C8 C9 -65.1(3) . . . . ?
C7 O1 C8 C17 178.1(2) . . . . ?
O1 C8 C9 C14 130.1(3) . . . . ?
C16 C8 C9 C14 4.4(4) . . . . ?
C17 C8 C9 C14 -118.7(3) . . . . ?
O1 C8 C9 C10 -49.8(3) . . . . ?
C16 C8 C9 C10 -175.5(2) . . . . ?
C17 C8 C9 C10 61.4(3) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 0.2(5) . . . . ?
C10 C11 C12 C13 -1.1(4) . . . . ?
C10 C11 C12 C15 179.6(3) . . . . ?
C11 C12 C13 C14 1.3(4) . . . . ?
C15 C12 C13 C14 -179.3(3) . . . . ?
C12 C13 C14 C9 -0.8(4) . . . . ?
C10 C9 C14 C13 -0.1(4) . . . . ?
C8 C9 C14 C13 180.0(3) . . . . ?
C11 C12 C15 F3 132.3(3) . . . . ?
C13 C12 C15 F3 -47.0(4) . . . . ?
C11 C12 C15 F1 8.3(4) . . . . ?
C13 C12 C15 F1 -171.0(3) . . . . ?
C11 C12 C15 F2 -110.1(3) . . . . ?
C13 C12 C15 F2 70.6(4) . . . . ?
O1 C8 C16 Br1 52.5(3) . . . . ?
C9 C8 C16 Br1 176.26(18) . . . . ?
C17 C8 C16 Br1 -60.9(3) . . . . ?
Si1 O2 C17 C8 -142.0(2) . . . . ?
O1 C8 C17 O2 -177.4(2) . . . . ?
C16 C8 C17 O2 -56.9(3) . . . . ?
C9 C8 C17 O2 66.4(3) . . . . ?
C40 Si2 O4 C37 167.7(2) . . . . ?
C39 Si2 O4 C37 -71.8(2) . . . . ?
C38 Si2 O4 C37 47.5(2) . . . . ?
C26 C21 C22 C23 -0.2(5) . . . . ?
C21 C22 C23 C24 0.2(5) . . . . ?
C22 C23 C24 C25 -0.3(5) . . . . ?
C23 C24 C25 C26 0.5(5) . . . . ?
C22 C21 C26 C25 0.4(5) . . . . ?
C22 C21 C26 C27 -179.8(3) . . . . ?
C24 C25 C26 C21 -0.5(5) . . . . ?
C24 C25 C26 C27 179.7(3) . . . . ?
C28 O3 C27 C26 166.3(2) . . . . ?
C21 C26 C27 O3 169.0(3) . . . . ?
C25 C26 C27 O3 -11.3(4) . . . . ?
C27 O3 C28 C36 167.8(2) . . . . ?
C27 O3 C28 C29 52.7(3) . . . . ?
C27 O3 C28 C37 -72.9(3) . . . . ?
O3 C28 C29 C34 -128.9(3) . . . . ?
C36 C28 C29 C34 116.7(3) . . . . ?
C37 C28 C29 C34 -6.3(4) . . . . ?
O3 C28 C29 C30 50.0(3) . . . . ?
C36 C28 C29 C30 -64.4(3) . . . . ?
C37 C28 C29 C30 172.6(2) . . . . ?
C34 C29 C30 C31 -0.4(4) . . . . ?
C28 C29 C30 C31 -179.3(3) . . . . ?
C29 C30 C31 C32 0.1(5) . . . . ?
C30 C31 C32 C33 0.1(5) . . . . ?
C30 C31 C32 C35B 177.6(3) . . . . ?
C30 C31 C32 C35 177.6(3) . . . . ?
C30 C31 C32 C35A 177.6(3) . . . . ?
C31 C32 C33 C34 0.1(5) . . . . ?
C35B C32 C33 C34 -177.5(3) . . . . ?
C35 C32 C33 C34 -177.5(3) . . . . ?
C35A C32 C33 C34 -177.5(3) . . . . ?
C32 C33 C34 C29 -0.4(4) . . . . ?
C30 C29 C34 C33 0.5(4) . . . . ?
C28 C29 C34 C33 179.4(3) . . . . ?
C33 C32 C35 F4 -138.8(8) . . . . ?
C31 C32 C35 F4 43.7(9) . . . . ?
C33 C32 C35 F6 -9.0(12) . . . . ?
C31 C32 C35 F6 173.5(11) . . . . ?
C33 C32 C35 F5 105.4(7) . . . . ?
C31 C32 C35 F5 -72.2(8) . . . . ?
C33 C32 C35A F4A -108.7(19) . . . . ?
C31 C32 C35A F4A 73.7(19) . . . . ?
C33 C32 C35A F5A 128.4(18) . . . . ?
C31 C32 C35A F5A -49.1(18) . . . . ?
C33 C32 C35A F6A 21(2) . . . . ?
C31 C32 C35A F6A -156.8(19) . . . . ?
C33 C32 C35B F5B 74.7(15) . . . . ?
C31 C32 C35B F5B -102.9(15) . . . . ?
C33 C32 C35B F4B -158.7(10) . . . . ?
C31 C32 C35B F4B 23.8(10) . . . . ?
C33 C32 C35B F6B -49.6(10) . . . . ?
C31 C32 C35B F6B 132.9(10) . . . . ?
O3 C28 C36 Br2 57.8(2) . . . . ?
C29 C28 C36 Br2 175.58(18) . . . . ?
C37 C28 C36 Br2 -59.8(3) . . . . ?
Si2 O4 C37 C28 176.23(18) . . . . ?
O3 C28 C37 O4 -167.3(2) . . . . ?
C36 C28 C37 O4 -51.6(3) . . . . ?
C29 C28 C37 O4 68.9(3) . . . . ?
