#------------------------------------------------------------------------------
#$Date: 2019-11-25 12:56:34 +0200 (Mon, 25 Nov 2019) $
#$Revision: 240904 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/04/4130483.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_4130483
loop_
_publ_author_name
'Hua, Yuanda'
'Asgari, Parham'
'Avullala, Thirupataiah'
'Jeon, Junha'
_publ_section_title
;
 Catalytic Reductive ortho-C-H Silylation of Phenols with Traceless,
 Versatile Acetal Directing Groups and Synthetic Applications of
 Dioxasilines.
;
_journal_issue                   25
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7982
_journal_page_last               7991
_journal_paper_doi               10.1021/jacs.6b04018
_journal_volume                  138
_journal_year                    2016
_chemical_formula_moiety         'C32 H38 O2 Si2'
_chemical_formula_sum            'C32 H38 O2 Si2'
_chemical_formula_weight         510.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 115.3270(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   26.3946(14)
_cell_length_b                   11.3169(6)
_cell_length_c                   21.4863(12)
_cell_measurement_reflns_used    9442
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      39.69
_cell_measurement_theta_min      2.93
_cell_volume                     5801.2(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            51174
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         33.142
_diffrn_reflns_theta_min         2.933
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       needle
_exptl_crystal_F_000             2192
_exptl_crystal_size_max          0.598
_exptl_crystal_size_mid          0.354
_exptl_crystal_size_min          0.219
_refine_diff_density_max         1.063
_refine_diff_density_min         -0.530
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     331
_refine_ls_number_reflns         11030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0433
_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)+(0.1400P)²+0.6304P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1609
_refine_ls_wR_factor_ref         0.1751
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9418
_reflns_number_total             11030
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja6b04018_si_002.cif
_cod_data_source_block           parham1_0m_a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4130483
_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   0.916
_shelx_estimated_absorpt_t_max   0.968
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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
Si1 Si 0.63031(2) 0.22886(2) 0.67551(2) 0.01638(8) Uani 1 1 d . .
O1 O 0.51618(3) 0.21746(7) 0.67629(4) 0.02313(16) Uani 1 1 d . .
H1 H 0.4830 0.2078 0.6708 0.035 Uiso 1 1 calc R U
C1 C 0.60679(4) 0.13502(8) 0.73092(5) 0.01493(16) Uani 1 1 d . .
C2 C 0.64322(4) 0.06008(8) 0.78041(5) 0.01516(16) Uani 1 1 d . .
H2A H 0.6813 0.0582 0.7875 0.018 Uiso 1 1 calc R U
C3 C 0.62626(3) -0.01452(8) 0.82128(4) 0.01445(15) Uani 1 1 d . .
C4 C 0.66483(4) -0.08919(9) 0.87260(5) 0.01870(17) Uani 1 1 d . .
H4 H 0.7033 -0.0874 0.8814 0.022 Uiso 1 1 calc R U
C5 C 0.64738(4) -0.16415(9) 0.90990(5) 0.02176(19) Uani 1 1 d . .
H5 H 0.6737 -0.2138 0.9442 0.026 Uiso 1 1 calc R U
C6 C 0.59029(4) -0.16716(9) 0.89706(5) 0.02062(18) Uani 1 1 d . .
H6 H 0.5783 -0.2192 0.9229 0.025 Uiso 1 1 calc R U
C7 C 0.55169(4) -0.09552(9) 0.84753(5) 0.01713(17) Uani 1 1 d . .
H7 H 0.5134 -0.0990 0.8393 0.021 Uiso 1 1 calc R U
C8 C 0.56873(3) -0.01644(8) 0.80869(4) 0.01353(15) Uani 1 1 d . .
C9 C 0.53040(3) 0.06070(8) 0.75765(4) 0.01360(15) Uani 1 1 d . .
C10 C 0.55013(4) 0.13592(8) 0.72250(5) 0.01532(16) Uani 1 1 d . .
C11 C 0.70186(5) 0.17623(10) 0.68995(6) 0.0263(2) Uani 1 1 d . .
H11A H 0.7279 0.1895 0.7388 0.032 Uiso 1 1 calc R U
H11B H 0.7002 0.0901 0.6813 0.032 Uiso 1 1 calc R U
C12 C 0.72529(6) 0.23722(14) 0.64449(9) 0.0423(4) Uani 1 1 d . .
H12A H 0.7028 0.2153 0.5963 0.063 Uiso 1 1 calc R U
H12B H 0.7642 0.2125 0.6585 0.063 Uiso 1 1 calc R U
H12C H 0.7239 0.3231 0.6495 0.063 Uiso 1 1 calc R U
C13 C 0.63374(6) 0.38853(10) 0.70003(7) 0.0292(2) Uani 1 1 d . .
H13 H 0.6019 0.4362 0.6747 0.035 Uiso 1 1 calc R U
C14 C 0.67738(8) 0.43994(15) 0.75014(10) 0.0487(4) Uani 1 1 d . .
H14A H 0.7100 0.3951 0.7766 0.058 Uiso 1 1 calc R U
H14B H 0.6760 0.5216 0.7596 0.058 Uiso 1 1 calc R U
C15 C 0.58037(5) 0.21540(13) 0.58300(6) 0.0315(3) Uani 1 1 d . .
H15A H 0.5459 0.2597 0.5753 0.038 Uiso 1 1 calc R U
H15B H 0.5973 0.2534 0.5549 0.038 Uiso 1 1 calc R U
C16 C 0.56416(10) 0.08953(17) 0.55748(8) 0.0567(5) Uani 1 1 d . .
H16A H 0.5979 0.0447 0.5643 0.085 Uiso 1 1 calc R U
H16B H 0.5385 0.0907 0.5084 0.085 Uiso 1 1 calc R U
H16C H 0.5456 0.0520 0.5833 0.085 Uiso 1 1 calc R U
Si2 Si 0.37154(2) 0.37601(2) 0.53369(2) 0.01799(8) Uani 1 1 d . .
O2 O 0.42526(4) 0.37755(7) 0.68938(4) 0.02303(16) Uani 1 1 d . .
H2 H 0.4366 0.3836 0.7322 0.035 Uiso 1 1 calc R U
C17 C 0.43375(4) 0.46373(8) 0.59435(4) 0.01620(16) Uani 1 1 d . .
C18 C 0.46238(4) 0.53863(9) 0.57002(4) 0.01638(16) Uani 1 1 d . .
H18 H 0.4514 0.5427 0.5218 0.020 Uiso 1 1 calc R U
C19 C 0.50776(4) 0.60994(8) 0.61438(4) 0.01544(16) Uani 1 1 d . .
C20 C 0.53690(4) 0.68545(9) 0.58804(5) 0.02019(18) Uani 1 1 d . .
H20 H 0.5262 0.6879 0.5399 0.024 Uiso 1 1 calc R U
C21 C 0.58027(5) 0.75490(10) 0.63125(6) 0.0238(2) Uani 1 1 d . .
H21 H 0.5996 0.8049 0.6131 0.029 Uiso 1 1 calc R U
C22 C 0.59615(5) 0.75182(10) 0.70303(6) 0.0233(2) Uani 1 1 d . .
H22 H 0.6266 0.7990 0.7330 0.028 Uiso 1 1 calc R U
C23 C 0.56797(4) 0.68107(9) 0.73005(5) 0.01912(17) Uani 1 1 d . .
H23 H 0.5787 0.6811 0.7783 0.023 Uiso 1 1 calc R U
C24 C 0.52307(4) 0.60823(8) 0.68648(4) 0.01475(16) Uani 1 1 d . .
C25 C 0.49353(4) 0.53143(8) 0.71261(4) 0.01517(16) Uani 1 1 d . .
C26 C 0.45200(4) 0.45920(8) 0.66709(5) 0.01628(16) Uani 1 1 d . .
C27 C 0.34829(5) 0.44390(11) 0.44595(5) 0.0253(2) Uani 1 1 d . .
H27A H 0.3400 0.5285 0.4487 0.030 Uiso 1 1 calc R U
H27B H 0.3796 0.4393 0.4322 0.030 Uiso 1 1 calc R U
C28 C 0.29731(5) 0.38597(13) 0.39092(6) 0.0344(3) Uani 1 1 d . .
H28A H 0.3057 0.3031 0.3860 0.052 Uiso 1 1 calc R U
H28B H 0.2871 0.4272 0.3471 0.052 Uiso 1 1 calc R U
H28C H 0.2660 0.3900 0.4040 0.052 Uiso 1 1 calc R U
C29 C 0.39270(5) 0.21952(10) 0.53106(5) 0.0232(2) Uani 1 1 d . .
H29 H 0.4275 0.2048 0.5294 0.028 Uiso 1 1 calc R U
C30 C 0.36199(7) 0.12899(11) 0.53138(9) 0.0412(3) Uani 1 1 d . .
H30A H 0.3270 0.1413 0.5330 0.049 Uiso 1 1 calc R U
H30B H 0.3747 0.0509 0.5300 0.049 Uiso 1 1 calc R U
C31 C 0.31195(5) 0.38165(11) 0.55918(6) 0.0263(2) Uani 1 1 d . .
H31A H 0.2794 0.3397 0.5240 0.032 Uiso 1 1 calc R U
H31B H 0.3231 0.3391 0.6033 0.032 Uiso 1 1 calc R U
C32 C 0.29397(6) 0.50737(14) 0.56718(8) 0.0388(3) Uani 1 1 d . .
H32A H 0.3250 0.5476 0.6045 0.058 Uiso 1 1 calc R U
H32B H 0.2615 0.5039 0.5780 0.058 Uiso 1 1 calc R U
H32C H 0.2839 0.5510 0.5241 0.058 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'
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_3
C15 Si1 C13 107.82(6) .
C15 Si1 C11 110.69(6) .
C13 Si1 C11 109.62(6) .
C15 Si1 C1 110.71(5) .
C13 Si1 C1 110.78(5) .
C11 Si1 C1 107.25(4) .
C10 O1 H1 109.5 .
C2 C1 C10 116.70(8) .
C2 C1 Si1 121.59(7) .
C10 C1 Si1 121.69(7) .
C1 C2 C3 122.83(8) .
C1 C2 H2A 118.6 .
C3 C2 H2A 118.6 .
C4 C3 C2 121.60(8) .
C4 C3 C8 119.45(8) .
C2 C3 C8 118.92(8) .
C5 C4 C3 120.90(9) .
C5 C4 H4 119.6 .
C3 C4 H4 119.6 .
C4 C5 C6 119.80(9) .
C4 C5 H5 120.1 .
C6 C5 H5 120.1 .
C7 C6 C5 120.76(9) .
C7 C6 H6 119.6 .
C5 C6 H6 119.6 .
C6 C7 C8 120.56(9) .
C6 C7 H7 119.7 .
C8 C7 H7 119.7 .
C7 C8 C3 118.52(8) .
C7 C8 C9 122.52(8) .
C3 C8 C9 118.96(8) .
C10 C9 C8 119.23(8) .
C10 C9 C9 120.07(8) 2_656
C8 C9 C9 120.70(7) 2_656
O1 C10 C9 121.95(8) .
O1 C10 C1 114.92(8) .
C9 C10 C1 123.13(8) .
C12 C11 Si1 113.93(8) .
C12 C11 H11A 108.8 .
Si1 C11 H11A 108.8 .
C12 C11 H11B 108.8 .
Si1 C11 H11B 108.8 .
H11A C11 H11B 107.7 .
C11 C12 H12A 109.5 .
C11 C12 H12B 109.5 .
H12A C12 H12B 109.5 .
C11 C12 H12C 109.5 .
H12A C12 H12C 109.5 .
H12B C12 H12C 109.5 .
C14 C13 Si1 124.84(12) .
C14 C13 H13 117.6 .
Si1 C13 H13 117.6 .
C13 C14 H14A 120.0 .
C13 C14 H14B 120.0 .
H14A C14 H14B 120.0 .
C16 C15 Si1 115.02(10) .
C16 C15 H15A 108.5 .
Si1 C15 H15A 108.5 .
C16 C15 H15B 108.5 .
Si1 C15 H15B 108.5 .
H15A C15 H15B 107.5 .
C15 C16 H16A 109.5 .
C15 C16 H16B 109.5 .
H16A C16 H16B 109.5 .
C15 C16 H16C 109.5 .
H16A C16 H16C 109.5 .
H16B C16 H16C 109.5 .
C29 Si2 C31 109.92(5) .
C29 Si2 C27 109.35(5) .
C31 Si2 C27 108.93(5) .
C29 Si2 C17 109.73(5) .
C31 Si2 C17 111.82(5) .
C27 Si2 C17 107.01(5) .
C26 O2 H2 109.5 .
C18 C17 C26 117.05(8) .
C18 C17 Si2 121.24(7) .
C26 C17 Si2 121.68(7) .
C17 C18 C19 122.45(8) .
C17 C18 H18 118.8 .
C19 C18 H18 118.8 .
C20 C19 C18 121.31(8) .
C20 C19 C24 119.48(9) .
C18 C19 C24 119.18(8) .
C21 C20 C19 120.86(9) .
C21 C20 H20 119.6 .
C19 C20 H20 119.6 .
C20 C21 C22 119.73(9) .
C20 C21 H21 120.1 .
C22 C21 H21 120.1 .
C23 C22 C21 120.77(10) .
C23 C22 H22 119.6 .
C21 C22 H22 119.6 .
C22 C23 C24 120.58(9) .
C22 C23 H23 119.7 .
C24 C23 H23 119.7 .
C23 C24 C19 118.56(8) .
C23 C24 C25 122.36(8) .
C19 C24 C25 119.07(8) .
C26 C25 C24 118.78(8) .
C26 C25 C25 120.60(8) 2_656
C24 C25 C25 120.61(8) 2_656
O2 C26 C25 121.58(8) .
O2 C26 C17 115.16(8) .
C25 C26 C17 123.26(8) .
C28 C27 Si2 114.05(9) .
C28 C27 H27A 108.7 .
Si2 C27 H27A 108.7 .
C28 C27 H27B 108.7 .
Si2 C27 H27B 108.7 .
H27A C27 H27B 107.6 .
C27 C28 H28A 109.5 .
C27 C28 H28B 109.5 .
H28A C28 H28B 109.5 .
C27 C28 H28C 109.5 .
H28A C28 H28C 109.5 .
H28B C28 H28C 109.5 .
C30 C29 Si2 123.32(10) .
C30 C29 H29 118.3 .
Si2 C29 H29 118.3 .
C29 C30 H30A 120.0 .
C29 C30 H30B 120.0 .
H30A C30 H30B 120.0 .
C32 C31 Si2 113.78(9) .
C32 C31 H31A 108.8 .
Si2 C31 H31A 108.8 .
C32 C31 H31B 108.8 .
Si2 C31 H31B 108.8 .
H31A C31 H31B 107.7 .
C31 C32 H32A 109.5 .
C31 C32 H32B 109.5 .
H32A C32 H32B 109.5 .
C31 C32 H32C 109.5 .
H32A C32 H32C 109.5 .
H32B C32 H32C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Si1 C15 1.8629(12) .
Si1 C13 1.8735(12) .
Si1 C11 1.8754(11) .
Si1 C1 1.8874(9) .
O1 C10 1.3708(11) .
O1 H1 0.8400 .
C1 C2 1.3783(12) .
C1 C10 1.4277(12) .
C2 C3 1.4213(12) .
C2 H2A 0.9500 .
C3 C4 1.4163(12) .
C3 C8 1.4242(12) .
C4 C5 1.3748(14) .
C4 H4 0.9500 .
C5 C6 1.4113(14) .
C5 H5 0.9500 .
C6 C7 1.3786(14) .
C6 H6 0.9500 .
C7 C8 1.4215(12) .
C7 H7 0.9500 .
C8 C9 1.4279(12) .
C9 C10 1.3796(12) .
C9 C9 1.4938(16) 2_656
C11 C12 1.5265(16) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
C13 C14 1.328(2) .
C13 H13 0.9500 .
C14 H14A 0.9500 .
C14 H14B 0.9500 .
C15 C16 1.521(2) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
Si2 C29 1.8650(11) .
Si2 C31 1.8747(12) .
Si2 C27 1.8791(11) .
Si2 C17 1.8840(9) .
O2 C26 1.3677(12) .
O2 H2 0.8400 .
C17 C18 1.3787(13) .
C17 C26 1.4259(12) .
C18 C19 1.4205(13) .
C18 H18 0.9500 .
C19 C20 1.4192(13) .
C19 C24 1.4241(12) .
C20 C21 1.3715(15) .
C20 H20 0.9500 .
C21 C22 1.4152(15) .
C21 H21 0.9500 .
C22 C23 1.3787(14) .
C22 H22 0.9500 .
C23 C24 1.4182(13) .
C23 H23 0.9500 .
C24 C25 1.4328(13) .
C25 C26 1.3816(13) .
C25 C25 1.4929(17) 2_656
C27 C28 1.5090(16) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
C29 C30 1.3081(18) .
C29 H29 0.9500 .
C30 H30A 0.9500 .
C30 H30B 0.9500 .
C31 C32 1.5325(18) .
C31 H31A 0.9900 .
C31 H31B 0.9900 .
C32 H32A 0.9800 .
C32 H32B 0.9800 .
C32 H32C 0.9800 .
