#------------------------------------------------------------------------------
#$Date: 2020-06-04 04:06:12 +0300 (Thu, 04 Jun 2020) $
#$Revision: 252607 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/49/4134902.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_4134902
loop_
_publ_author_name
'Ding, Wei'
'Chai, Jinkui'
'Wang, Chen'
'Wu, Junliang'
'Yoshikai, Naohiko'
_publ_section_title
;
 Stereoselective Access to Highly Substituted Vinyl Ethers via
 trans-Difunctionalization of Alkynes with Alcohols and Iodine(III)
 Electrophile.
;
_journal_issue                   19
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              8619
_journal_page_last               8624
_journal_paper_doi               10.1021/jacs.0c04140
_journal_volume                  142
_journal_year                    2020
_chemical_formula_sum            'C15 H17 F6 I O2 Si'
_chemical_formula_weight         498.27
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                116.9442(13)
_cell_angle_beta                 95.0969(14)
_cell_angle_gamma                102.6202(15)
_cell_formula_units_Z            2
_cell_length_a                   7.4420(3)
_cell_length_b                   11.8848(5)
_cell_length_c                   12.5542(5)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    174.(2)
_cell_measurement_theta_max      31.0257
_cell_measurement_theta_min      2.8726
_cell_volume                     943.14(7)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2016)'
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2016)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      174.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0357
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            18916
_diffrn_reflns_theta_full        31.05
_diffrn_reflns_theta_max         31.05
_diffrn_reflns_theta_min         2.87
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    1.823
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.72
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.164
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.712
_refine_diff_density_min         -0.810
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         6005
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0302
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0108P)²+0.5989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0556
_reflns_number_gt                5165
_reflns_number_total             6005
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja0c04140_si_005.cif
_cod_data_source_block           yoshi59m
_cod_depositor_comments
'Adding full bibliography for 4134900--4134903.cif.'
_cod_database_code               4134902
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4462(3) 0.6791(2) 0.30721(18) 0.0225(4) Uani d . . . 1 . .
C C2 0.3352(3) 0.6854(2) 0.3913(2) 0.0263(4) Uani d . . . 1 . .
H H2 0.2215 0.6174 0.3693 0.032 Uiso calc U . R 1 . .
C C3 0.3932(3) 0.7930(2) 0.5085(2) 0.0304(5) Uani d . . . 1 . .
H H3 0.3176 0.7999 0.5671 0.036 Uiso calc U . R 1 . .
C C4 0.5596(3) 0.8896(2) 0.5400(2) 0.0311(5) Uani d . . . 1 . .
H H4 0.6 0.962 0.6209 0.037 Uiso calc U . R 1 . .
C C5 0.6690(3) 0.8820(2) 0.45454(19) 0.0279(5) Uani d . . . 1 . .
H H5 0.7838 0.9493 0.4775 0.033 Uiso calc U . R 1 . .
C C6 0.6124(3) 0.7769(2) 0.33543(18) 0.0223(4) Uani d . . . 1 . .
C C7 0.7226(3) 0.7635(2) 0.23376(19) 0.0244(4) Uani d . . . 1 . .
C C8 0.8999(3) 0.7263(3) 0.2619(2) 0.0350(5) Uani d . . . 1 . .
C C9 0.7799(4) 0.8949(2) 0.2305(2) 0.0331(5) Uani d . . . 1 . .
C C10 0.1673(3) 0.3923(2) 0.17299(19) 0.0254(4) Uani d . . . 1 . .
C C11 -0.0069(3) 0.3589(2) 0.1079(2) 0.0305(5) Uani d . . . 1 . .
H H11 -0.0294 0.3991 0.0597 0.037 Uiso calc U . R 1 . .
C C12 -0.3167(4) 0.2199(3) 0.0170(3) 0.0514(8) Uani d . . . 1 . .
H H12A -0.3629 0.2936 0.024 0.077 Uiso calc U . R 1 . .
H H12B -0.4139 0.1574 0.0272 0.077 Uiso calc U . R 1 . .
H H12C -0.2873 0.1752 -0.0638 0.077 Uiso calc U . R 1 . .
C C13 0.1019(4) 0.3382(3) 0.3837(3) 0.0506(7) Uani d . . . 1 . .
H H13A -0.0327 0.2987 0.3454 0.076 Uiso calc U . R 1 . .
H H13B 0.1268 0.4329 0.4391 0.076 Uiso calc U . R 1 . .
H H13C 0.1383 0.2961 0.4301 0.076 Uiso calc U . R 1 . .
C C14 0.4979(4) 0.3920(3) 0.3322(2) 0.0384(6) Uani d . . . 1 . .
H H14A 0.5367 0.3583 0.386 0.058 Uiso calc U . R 1 . .
H H14B 0.5231 0.4879 0.3799 0.058 Uiso calc U . R 1 . .
H H14C 0.5691 0.3711 0.2671 0.058 Uiso calc U . R 1 . .
C C15 0.1982(4) 0.1349(3) 0.1573(3) 0.0474(7) Uani d . . . 1 . .
H H15A 0.2686 0.1235 0.0926 0.071 Uiso calc U . R 1 . .
H H15B 0.0631 0.0935 0.1206 0.071 Uiso calc U . R 1 . .
H H15C 0.24 0.0932 0.2028 0.071 Uiso calc U . R 1 . .
F F1 1.0112(2) 0.81211(16) 0.37230(14) 0.0498(4) Uani d . . . 1 . .
F F2 0.8499(2) 0.60961(16) 0.25884(16) 0.0495(4) Uani d . . . 1 . .
F F3 1.0075(2) 0.71414(19) 0.18041(16) 0.0572(5) Uani d . . . 1 . .
F F4 0.8492(2) 0.87917(16) 0.13217(14) 0.0525(4) Uani d . . . 1 . .
F F5 0.9101(2) 0.99379(14) 0.32749(14) 0.0475(4) Uani d . . . 1 . .
F F6 0.6302(2) 0.93827(15) 0.22432(14) 0.0435(4) Uani d . . . 1 . .
I I1 0.36921(2) 0.51188(2) 0.13048(2) 0.02256(4) Uani d . . . 1 . .
O O1 0.6170(2) 0.66968(15) 0.12158(13) 0.0276(3) Uani d . . . 1 . .
O O2 -0.1499(2) 0.26898(19) 0.11005(17) 0.0425(5) Uani d . . . 1 . .
Si Si1 0.24138(10) 0.31365(7) 0.26314(6) 0.03041(14) Uani d . . . 1 . .
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 122.4(2) ?
C2 C1 I1 . . 119.68(15) ?
C6 C1 I1 . . 117.85(15) ?
C1 C2 C3 . . 118.7(2) ?
C4 C3 C2 . . 120.2(2) ?
C3 C4 C5 . . 120.4(2) ?
C4 C5 C6 . . 120.8(2) ?
C1 C6 C5 . . 117.5(2) ?
C1 C6 C7 . . 118.50(18) ?
C5 C6 C7 . . 124.03(19) ?
O1 C7 C8 . . 109.84(19) ?
O1 C7 C6 . . 111.60(17) ?
C8 C7 C6 . . 107.63(17) ?
O1 C7 C9 . . 107.17(17) ?
C8 C7 C9 . . 110.04(19) ?
C6 C7 C9 . . 110.58(18) ?
F3 C8 F2 . . 106.4(2) ?
F3 C8 F1 . . 106.8(2) ?
F2 C8 F1 . . 106.3(2) ?
F3 C8 C7 . . 112.7(2) ?
F2 C8 C7 . . 109.94(19) ?
F1 C8 C7 . . 114.1(2) ?
F4 C9 F6 . . 106.9(2) ?
F4 C9 F5 . . 106.45(19) ?
F6 C9 F5 . . 106.4(2) ?
F4 C9 C7 . . 111.0(2) ?
F6 C9 C7 . . 110.62(19) ?
F5 C9 C7 . . 114.96(19) ?
C11 C10 Si1 . . 125.36(17) ?
C11 C10 I1 . . 112.08(16) ?
Si1 C10 I1 . . 121.06(11) ?
C10 C11 O2 . . 120.7(2) ?
C10 I1 C1 . . 95.83(8) ?
C10 I1 O1 . . 169.63(7) ?
C1 I1 O1 . . 74.34(7) ?
C7 O1 I1 . . 112.76(12) ?
C11 O2 C12 . . 115.2(2) ?
C15 Si1 C14 . . 109.39(14) ?
C15 Si1 C13 . . 110.41(14) ?
C14 Si1 C13 . . 110.94(13) ?
C15 Si1 C10 . . 108.69(11) ?
C14 Si1 C10 . . 108.29(10) ?
C13 Si1 C10 . . 109.06(13) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.383(3) ?
C1 C6 . 1.389(3) ?
C1 I1 . 2.117(2) ?
C2 C3 . 1.389(3) ?
C3 C4 . 1.374(3) ?
C4 C5 . 1.386(3) ?
C5 C6 . 1.392(3) ?
C6 C7 . 1.544(3) ?
C7 O1 . 1.357(2) ?
C7 C8 . 1.541(3) ?
C7 C9 . 1.547(3) ?
C8 F3 . 1.331(3) ?
C8 F2 . 1.337(3) ?
C8 F1 . 1.339(3) ?
C9 F4 . 1.330(3) ?
C9 F6 . 1.336(3) ?
C9 F5 . 1.341(3) ?
C10 C11 . 1.341(3) ?
C10 Si1 . 1.879(2) ?
C10 I1 . 2.112(2) ?
C11 O2 . 1.345(3) ?
C12 O2 . 1.433(3) ?
C13 Si1 . 1.861(3) ?
C14 Si1 . 1.861(3) ?
C15 Si1 . 1.858(3) ?
I1 O1 . 2.3763(15) ?
