#------------------------------------------------------------------------------
#$Date: 2019-11-26 16:36:47 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243645 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/94/4089443.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_4089443
loop_
_publ_author_name
'Laskowski, Nadine'
'Reis, Eva-Maria'
'Kötzner, Lisa'
'Baus, Johannes A.'
'Burschka, Christian'
'Tacke, Reinhold'
_publ_section_title
;
 Synthesis of Silicon-Functionalized (Silylmethyl)silanes and
 α,ω-Dichlorocarbosilanes Using the TMOP (2,4,6-Trimethoxyphenyl)
 Protecting Group: (TMOP)Me2SiCH2Cl and (TMOP)2MeSiCH2Cl as Reagents To
 Introduce the ClMe2SiCH2, MeOMe2SiCH2, or Cl2MeSiCH2 Group by
 Nucleophilic Substitution at Silicon
;
_journal_issue                   11
_journal_name_full               Organometallics
_journal_page_first              3269
_journal_paper_doi               10.1021/om400190q
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C15 H28 O3 Si2'
_chemical_formula_sum            'C15 H28 O3 Si2'
_chemical_formula_weight         312.55
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8734(18)
_cell_length_b                   25.995(5)
_cell_length_c                   8.1597(16)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      26.5
_cell_measurement_theta_min      7.45
_cell_volume                     1869.0(6)
_computing_cell_refinement       Stoe-IPDS
_computing_data_collection       Stoe-IPDS
_computing_data_reduction        Stoe-IPDS
_computing_molecular_graphics    Ortep/Povray
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  Stoe-IPDS_image_plate
_diffrn_measurement_method       omega_scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20439
_diffrn_reflns_theta_full        27.89
_diffrn_reflns_theta_max         27.89
_diffrn_reflns_theta_min         3.90
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.111
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.330
_refine_diff_density_rms
'0.045 -2 28 -3 2.68 0.34 -2 25 -2 1.88 0.34 -5 25 -1 4.16 0.33 4 -19 -7 3.04 0.48 3 -23 -7 19.57 0.54 2 26 0.00'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         4188
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.073
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0674P)²+0.4976P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1279
_reflns_number_gt                3687
_reflns_number_total             4188
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400190q_si_001.cif
_cod_data_source_block           rei13e
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4089443
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
Si1 Si 0.33251(5) 0.662660(14) 0.08389(5) 0.03498(14) Uani 1 1 d .
Si2 Si 0.63052(5) 0.656904(17) 0.36419(6) 0.03948(14) Uani 1 1 d .
O1 O 0.34228(16) 0.55800(4) -0.10847(15) 0.0471(3) Uani 1 1 d .
O2 O 0.07924(14) 0.45458(4) 0.26147(14) 0.0397(3) Uani 1 1 d .
O3 O 0.18281(14) 0.63200(4) 0.36630(14) 0.0414(3) Uani 1 1 d .
C1 C 0.26436(17) 0.59550(5) 0.13027(18) 0.0320(3) Uani 1 1 d .
C2 C 0.27301(17) 0.55147(5) 0.03153(18) 0.0330(3) Uani 1 1 d .
C3 C 0.21401(18) 0.50354(5) 0.07082(18) 0.0332(3) Uani 1 1 d .
H3 H 0.2221 0.4746 0.0013 0.040 Uiso 1 1 calc R
C4 C 0.14376(17) 0.49925(5) 0.21299(18) 0.0321(3) Uani 1 1 d .
C5 C 0.13123(18) 0.54144(5) 0.31655(19) 0.0347(3) Uani 1 1 d .
H5 H 0.0828 0.5383 0.4139 0.042 Uiso 1 1 calc R
C6 C 0.19177(17) 0.58820(5) 0.27282(18) 0.0330(3) Uani 1 1 d .
C7 C 0.3540(2) 0.51467(6) -0.2139(2) 0.0481(4) Uani 1 1 d .
H7A H 0.4110 0.4872 -0.1520 0.072 Uiso 1 1 calc R
H7B H 0.4069 0.5248 -0.3077 0.072 Uiso 1 1 calc R
H7C H 0.2521 0.5022 -0.2544 0.072 Uiso 1 1 calc R
C8 C 0.0906(2) 0.41038(6) 0.1585(2) 0.0424(4) Uani 1 1 d .
H8A H 0.0479 0.4185 0.0452 0.064 Uiso 1 1 calc R
H8B H 0.0343 0.3817 0.2000 0.064 Uiso 1 1 calc R
H8C H 0.1976 0.4007 0.1600 0.064 Uiso 1 1 calc R
C9 C 0.1248(2) 0.62725(6) 0.5206(2) 0.0436(4) Uani 1 1 d .
H9A H 0.0204 0.6143 0.5028 0.065 Uiso 1 1 calc R
H9B H 0.1261 0.6610 0.5744 0.065 Uiso 1 1 calc R
H9C H 0.1879 0.6032 0.5910 0.065 Uiso 1 1 calc R
C10 C 0.4395(2) 0.66483(6) -0.1008(2) 0.0471(4) Uani 1 1 d .
H10A H 0.4880 0.6985 -0.1067 0.071 Uiso 1 1 calc R
H10B H 0.3692 0.6592 -0.2011 0.071 Uiso 1 1 calc R
H10C H 0.5174 0.6379 -0.0912 0.071 Uiso 1 1 calc R
C11 C 0.1616(2) 0.70562(7) 0.0385(3) 0.0564(5) Uani 1 1 d .
H11A H 0.1949 0.7406 0.0156 0.085 Uiso 1 1 calc R
H11B H 0.1043 0.7062 0.1340 0.085 Uiso 1 1 calc R
H11C H 0.0967 0.6924 -0.0579 0.085 Uiso 1 1 calc R
C12 C 0.45816(19) 0.69091(5) 0.2625(2) 0.0373(3) Uani 1 1 d .
H12A H 0.4929 0.7247 0.2253 0.045 Uiso 1 1 calc R
H12B H 0.3926 0.6980 0.3500 0.045 Uiso 1 1 calc R
C13 C 0.7544(2) 0.63591(9) 0.2064(3) 0.0571(5) Uani 1 1 d .
H13A H 0.8441 0.6183 0.2613 0.086 Uiso 1 1 calc R
H13B H 0.7864 0.6661 0.1472 0.086 Uiso 1 1 calc R
H13C H 0.6978 0.6124 0.1280 0.086 Uiso 1 1 calc R
C14 C 0.5763(3) 0.59884(8) 0.4800(2) 0.0542(5) Uani 1 1 d .
H14A H 0.5137 0.5759 0.4047 0.081 Uiso 1 1 calc R
H14B H 0.5186 0.6096 0.5694 0.081 Uiso 1 1 calc R
H14C H 0.6682 0.5806 0.5266 0.081 Uiso 1 1 calc R
C15 C 0.7380(3) 0.70266(9) 0.5135(3) 0.0640(6) Uani 1 1 d .
H15A H 0.8255 0.6849 0.5728 0.096 Uiso 1 1 calc R
H15B H 0.6713 0.7150 0.5926 0.096 Uiso 1 1 calc R
H15C H 0.7734 0.7320 0.4529 0.096 Uiso 1 1 calc R
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
C10 Si1 C12 107.55(8)
C10 Si1 C11 107.24(10)
C12 Si1 C11 108.14(9)
C10 Si1 C1 113.02(7)
C12 Si1 C1 112.25(7)
C11 Si1 C1 108.42(8)
C13 Si2 C12 110.38(9)
C13 Si2 C14 108.60(10)
C12 Si2 C14 111.03(9)
C13 Si2 C15 109.63(11)
C12 Si2 C15 108.29(9)
C14 Si2 C15 108.88(11)
C2 O1 C7 118.43(12)
C4 O2 C8 116.62(12)
C6 O3 C9 117.99(12)
C2 C1 C6 115.13(12)
C2 C1 Si1 126.39(11)
C6 C1 Si1 118.42(10)
O1 C2 C3 121.11(13)
O1 C2 C1 115.90(12)
C3 C2 C1 122.99(14)
C4 C3 C2 118.69(13)
O2 C4 C3 123.62(13)
O2 C4 C5 115.08(13)
C3 C4 C5 121.28(13)
C6 C5 C4 118.01(14)
O3 C6 C5 122.02(14)
O3 C6 C1 114.07(12)
C5 C6 C1 123.89(13)
Si2 C12 Si1 122.58(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C10 1.8745(19)
Si1 C12 1.8769(17)
Si1 C11 1.8846(19)
Si1 C1 1.9002(14)
Si2 C13 1.871(2)
Si2 C12 1.8734(18)
Si2 C14 1.874(2)
Si2 C15 1.880(2)
O1 C2 1.3701(18)
O1 C7 1.4284(18)
O2 C4 1.3733(17)
O2 C8 1.4341(18)
O3 C6 1.3781(17)
O3 C9 1.421(2)
C1 C2 1.4070(19)
C1 C6 1.407(2)
C2 C3 1.4030(19)
C3 C4 1.385(2)
C4 C5 1.397(2)
C5 C6 1.392(2)
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
C10 Si1 C1 C2 -7.32(17)
C12 Si1 C1 C2 -129.18(14)
C11 Si1 C1 C2 111.42(16)
C10 Si1 C1 C6 175.61(12)
C12 Si1 C1 C6 53.75(14)
C11 Si1 C1 C6 -65.65(15)
C7 O1 C2 C3 -0.3(2)
C7 O1 C2 C1 -179.80(16)
C6 C1 C2 O1 179.49(13)
Si1 C1 C2 O1 2.3(2)
C6 C1 C2 C3 0.0(2)
Si1 C1 C2 C3 -177.13(12)
O1 C2 C3 C4 -179.33(14)
C1 C2 C3 C4 0.1(2)
C8 O2 C4 C3 1.6(2)
C8 O2 C4 C5 -179.68(14)
C2 C3 C4 O2 178.55(14)
C2 C3 C4 C5 -0.1(2)
O2 C4 C5 C6 -178.82(14)
C3 C4 C5 C6 -0.1(2)
C9 O3 C6 C5 7.1(2)
C9 O3 C6 C1 -173.96(14)
C4 C5 C6 O3 179.09(14)
C4 C5 C6 C1 0.2(2)
C2 C1 C6 O3 -179.15(13)
Si1 C1 C6 O3 -1.75(18)
C2 C1 C6 C5 -0.2(2)
Si1 C1 C6 C5 177.21(12)
C13 Si2 C12 Si1 51.43(13)
C14 Si2 C12 Si1 -69.07(13)
C15 Si2 C12 Si1 171.45(12)
C10 Si1 C12 Si2 -71.37(12)
C11 Si1 C12 Si2 173.12(11)
C1 Si1 C12 Si2 53.56(12)
