#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/28/1502865.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_1502865
loop_
_publ_author_name
'Smith, 3rd, Amos B'
'Tong, Rongbiao'
_publ_section_title
;
 Benzyl and phenylthiomethyl silanes: a new class of bifunctional
 linchpins for type II anion relay chemistry (ARC).
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1260
_journal_page_last               1263
_journal_paper_doi               10.1021/ol100130x
_journal_volume                  12
_journal_year                    2010
_chemical_formula_sum            'C21 H27 Br O3 Si'
_chemical_formula_weight         435.43
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.893(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   9.4119(16)
_cell_length_b                   9.3243(15)
_cell_length_c                   12.776(2)
_cell_measurement_temperature    143(1)
_cell_volume                     1072.8(3)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_sigmaI/netI    0.0488
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11767
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.75
_exptl_absorpt_coefficient_mu    1.988
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7570
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             452
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.022(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0340
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0311P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0669
_refine_ls_wR_factor_ref         0.0705
_reflns_number_gt                4101
_reflns_number_total             4684
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol100130x_si_004.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:
'_atom_site_symetry_multiplicity' tag replaced with
'_atom_site_symmetry_multiplicity'.

Automatic conversion script
Id: cif_correct_tags 1440 2010-10-19 06:21:57Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21     '
_cod_database_code               1502865
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C -0.0105(3) 0.6187(2) 0.3635(2) 0.0271(5) Uani 1 1 d .
C2 C 0.1497(3) 0.8061(3) 0.45361(19) 0.0300(6) Uani 1 1 d .
H2A H 0.1736 0.7599 0.5246 0.040 Uiso 1 1 calc R
H2B H 0.0681 0.8721 0.4478 0.040 Uiso 1 1 calc R
C3 C 0.2842(3) 0.8862(3) 0.44057(18) 0.0259(5) Uani 1 1 d .
H3 H 0.3631 0.8154 0.4465 0.034 Uiso 1 1 calc R
C4 C 0.2580(2) 0.9618(3) 0.32992(19) 0.0259(5) Uani 1 1 d .
H4 H 0.2336 0.8881 0.2727 0.034 Uiso 1 1 calc R
C5 C 0.4014(2) 1.0386(2) 0.32396(18) 0.0245(5) Uani 1 1 d .
H5 H 0.4284 1.1054 0.3858 0.033 Uiso 1 1 calc R
C6 C 0.3810(2) 1.1292(2) 0.22140(19) 0.0240(5) Uani 1 1 d .
C7 C 0.4257(3) 1.2739(3) 0.2291(2) 0.0299(6) Uani 1 1 d .
H7 H 0.4648 1.3156 0.2976 0.040 Uiso 1 1 calc R
C8 C 0.4123(3) 1.3548(3) 0.1359(2) 0.0339(6) Uani 1 1 d .
H8 H 0.4427 1.4502 0.1425 0.045 Uiso 1 1 calc R
C9 C 0.3543(3) 1.2957(3) 0.0334(2) 0.0382(7) Uani 1 1 d .
H9 H 0.3475 1.3500 -0.0290 0.051 Uiso 1 1 calc R
C10 C 0.3065(3) 1.1550(4) 0.02441(18) 0.0407(6) Uani 1 1 d .
H10 H 0.2650 1.1150 -0.0444 0.054 Uiso 1 1 calc R
C11 C 0.3198(3) 1.0729(3) 0.1171(2) 0.0357(6) Uani 1 1 d .
H11 H 0.2873 0.9782 0.1094 0.047 Uiso 1 1 calc R
C12 C -0.0403(3) 0.5100(3) 0.27499(18) 0.0261(5) Uani 1 1 d .
C13 C 0.0606(3) 0.4819(3) 0.2177(2) 0.0306(6) Uani 1 1 d .
H13 H 0.1505 0.5310 0.2350 0.041 Uiso 1 1 calc R
C14 C 0.0284(3) 0.3811(3) 0.1344(2) 0.0311(6) Uani 1 1 d .
H14 H 0.0962 0.3616 0.0959 0.041 Uiso 1 1 calc R
C15 C -0.1067(3) 0.3096(3) 0.1095(2) 0.0313(6) Uani 1 1 d .
C16 C -0.2086(3) 0.3362(3) 0.1656(2) 0.0344(6) Uani 1 1 d .
H16 H -0.2988 0.2877 0.1472 0.046 Uiso 1 1 calc R
C17 C -0.1756(3) 0.4358(3) 0.2497(2) 0.0309(6) Uani 1 1 d .
H17 H -0.2428 0.4534 0.2892 0.041 Uiso 1 1 calc R
C18 C 0.1266(3) 1.0673(3) 0.3070(2) 0.0381(6) Uani 1 1 d .
H18A H 0.0373 1.0158 0.3043 0.057 Uiso 1 1 calc R
H18B H 0.1155 1.1143 0.2382 0.057 Uiso 1 1 calc R
H18C H 0.1452 1.1377 0.3643 0.057 Uiso 1 1 calc R
C19 C 0.5090(3) 0.7379(3) 0.2746(2) 0.0408(7) Uani 1 1 d .
H19A H 0.4518 0.7525 0.1999 0.061 Uiso 1 1 calc R
H19B H 0.4493 0.6894 0.3130 0.061 Uiso 1 1 calc R
H19C H 0.5947 0.6807 0.2770 0.061 Uiso 1 1 calc R
C20 C 0.6717(3) 0.8934(3) 0.4895(2) 0.0377(7) Uani 1 1 d .
H20A H 0.7682 0.8537 0.4970 0.057 Uiso 1 1 calc R
H20B H 0.6169 0.8301 0.5228 0.057 Uiso 1 1 calc R
H20C H 0.6820 0.9852 0.5249 0.057 Uiso 1 1 calc R
C21 C 0.7014(3) 0.9956(3) 0.2740(2) 0.0444(7) Uani 1 1 d .
H21A H 0.7858 0.9338 0.2840 0.067 Uiso 1 1 calc R
H21B H 0.7335 1.0875 0.3062 0.067 Uiso 1 1 calc R
H21C H 0.6530 1.0073 0.1973 0.067 Uiso 1 1 calc R
O1 O 0.33327(19) 0.9813(2) 0.53162(14) 0.0308(4) Uani 1 1 d .
H1 H 0.2683 1.0406 0.5298 0.046 Uiso 1 1 calc R
O2 O 0.10858(17) 0.69937(18) 0.36694(12) 0.0295(4) Uani 1 1 d .
O3 O -0.08318(19) 0.63554(19) 0.42727(14) 0.0378(5) Uani 1 1 d .
Si1 Si 0.56969(7) 0.91511(8) 0.34070(5) 0.02759(16) Uani 1 1 d .
Br1 Br -0.15019(3) 0.17058(3) -0.00292(2) 0.05040(11) Uani 1 1 d .
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'
Br Br -0.2901 2.4595 '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
O3 C1 O2 122.3(2)
O3 C1 C12 125.4(2)
O2 C1 C12 112.3(2)
O2 C2 C3 107.35(19)
O1 C3 C2 107.33(19)
O1 C3 C4 113.2(2)
C2 C3 C4 114.21(18)
C3 C4 C18 112.0(2)
C3 C4 C5 110.37(17)
C18 C4 C5 111.0(2)
C6 C5 C4 113.87(18)
C6 C5 Si1 108.79(17)
C4 C5 Si1 114.80(16)
C11 C6 C7 117.4(2)
C11 C6 C5 121.9(2)
C7 C6 C5 120.7(2)
C8 C7 C6 120.8(3)
C9 C8 C7 120.7(3)
C8 C9 C10 119.2(3)
C9 C10 C11 120.5(2)
C10 C11 C6 121.3(3)
C13 C12 C17 120.2(2)
C13 C12 C1 121.8(2)
C17 C12 C1 118.0(2)
C12 C13 C14 120.3(2)
C13 C14 C15 118.9(2)
C16 C15 C14 121.6(2)
C16 C15 Br1 119.33(19)
C14 C15 Br1 119.1(2)
C15 C16 C17 119.5(2)
C16 C17 C12 119.5(2)
C1 O2 C2 116.31(19)
C21 Si1 C19 107.94(15)
C21 Si1 C20 107.23(13)
C19 Si1 C20 111.21(13)
C21 Si1 C5 110.23(13)
C19 Si1 C5 110.27(11)
C20 Si1 C5 109.90(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O3 1.216(3)
C1 O2 1.340(3)
C1 C12 1.484(3)
C2 O2 1.455(3)
C2 C3 1.521(3)
C3 O1 1.428(3)
C3 C4 1.534(3)
C4 C18 1.540(3)
C4 C5 1.550(3)
C5 C6 1.523(3)
C5 Si1 1.919(2)
C6 C11 1.392(3)
C6 C7 1.409(3)
C7 C8 1.383(4)
C8 C9 1.379(4)
C9 C10 1.381(5)
C10 C11 1.384(4)
C12 C13 1.382(3)
C12 C17 1.402(3)
C13 C14 1.386(3)
C14 C15 1.388(4)
C15 C16 1.377(4)
C15 Br1 1.889(3)
C16 C17 1.386(4)
C19 Si1 1.868(3)
C20 Si1 1.876(3)
C21 Si1 1.854(3)
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
O1 H1 O3 0.82 2.16 2.933(3) 156.6 2_556
