#------------------------------------------------------------------------------
#$Date: 2019-11-26 16:36:47 +0200 (Tue, 26 Nov 2019) $
#$Revision: 243645 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/94/4089445.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_4089445
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         'C13 H22 Cl2 O3 Si2'
_chemical_formula_sum            'C13 H22 Cl2 O3 Si2'
_chemical_formula_weight         353.39
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                106.910(6)
_cell_angle_beta                 100.409(6)
_cell_angle_gamma                97.462(6)
_cell_formula_units_Z            2
_cell_length_a                   8.136(3)
_cell_length_b                   8.797(3)
_cell_length_c                   13.306(5)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.59
_cell_volume                     879.2(6)
_computing_cell_refinement       Bruker-SAINT
_computing_data_collection       Bruker-SAINT
_computing_data_reduction        Bruker-SAINT
_computing_molecular_graphics    Ortep/Povray
_computing_publication_material  Bruker-SHELXTL
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker-Nonius_Kappa_Apex2_CCD
_diffrn_measurement_method       omega_and_phi_scans
_diffrn_radiation_monochromator  MONTEL_multi_layer_optics
_diffrn_radiation_source         rotating_anode
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0120
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            38749
_diffrn_reflns_theta_full        30.10
_diffrn_reflns_theta_max         30.10
_diffrn_reflns_theta_min         1.64
_exptl_absorpt_coefficient_mu    0.509
_exptl_absorpt_correction_T_max  .7460
_exptl_absorpt_correction_T_min  .6641
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             372
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .3
_exptl_crystal_size_min          .05
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.354
_refine_diff_density_rms
'0.049 -1 0 0 21.50 0.40 -1 0 0 21.54 0.41 -1 0 0 21.33 0.46 -1 0 0 21.31 0.41 -1 0 0 21.59 0.45 -1 0 0 21. 0.00'
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         5169
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0275
_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)+(0.0404P)²+0.3084P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0781
_refine_ls_wR_factor_ref         0.0814
_reflns_number_gt                4642
_reflns_number_total             5169
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400190q_si_001.cif
_cod_data_source_block           las10d
_cod_original_cell_volume        879.1(6)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4089445
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C13 C 1.06242(15) 1.16929(14) 0.19532(9) 0.0266(2) Uani 1 1 d .
H13A H 1.1602 1.1214 0.2158 0.040 Uiso 1 1 calc R
H13B H 1.0941 1.2441 0.1569 0.040 Uiso 1 1 calc R
H13C H 0.9673 1.0833 0.1482 0.040 Uiso 1 1 calc R
C12 C 0.90820(14) 1.16024(13) 0.39443(9) 0.0241(2) Uani 1 1 d .
H12A H 0.8935 1.2368 0.4618 0.029 Uiso 1 1 calc R
H12B H 0.9956 1.1000 0.4158 0.029 Uiso 1 1 calc R
C11 C 0.52623(15) 1.12777(15) 0.33216(10) 0.0305(2) Uani 1 1 d .
H11A H 0.4164 1.0544 0.3157 0.046 Uiso 1 1 calc R
H11B H 0.5265 1.1824 0.2777 0.046 Uiso 1 1 calc R
H11C H 0.5441 1.2087 0.4036 0.046 Uiso 1 1 calc R
C10 C 0.67550(18) 0.88119(16) 0.42029(10) 0.0328(3) Uani 1 1 d .
H10A H 0.6942 0.9512 0.4952 0.049 Uiso 1 1 calc R
H10B H 0.7589 0.8099 0.4151 0.049 Uiso 1 1 calc R
H10C H 0.5602 0.8155 0.3970 0.049 Uiso 1 1 calc R
C1 C 0.70145(13) 0.87075(12) 0.19298(8) 0.02089(19) Uani 1 1 d .
O1 O 0.43130(11) 0.90157(12) 0.11332(7) 0.0320(2) Uani 1 1 d .
Si1 Si 0.70092(4) 1.00930(4) 0.33129(2) 0.02151(7) Uani 1 1 d .
C2 C 0.56829(13) 0.82839(13) 0.10084(9) 0.02199(19) Uani 1 1 d .
O2 O 0.72762(11) 0.53261(10) -0.09730(7) 0.02842(17) Uani 1 1 d .
Si2 Si 0.99726(4) 1.28152(4) 0.31875(3) 0.02422(8) Uani 1 1 d .
C3 C 0.57108(14) 0.71694(13) 0.00188(8) 0.0229(2) Uani 1 1 d .
H3 H 0.4788 0.6919 -0.0590 0.028 Uiso 1 1 calc R
O3 O 0.96677(10) 0.83197(10) 0.27183(7) 0.02810(17) Uani 1 1 d .
C4 C 0.71198(14) 0.64380(13) -0.00512(9) 0.02226(19) Uani 1 1 d .
C6 C 0.83987(13) 0.79086(13) 0.18015(9) 0.02168(19) Uani 1 1 d .
C5 C 0.84786(14) 0.67957(13) 0.08349(9) 0.0238(2) Uani 1 1 d .
H5 H 0.9438 0.6291 0.0781 0.029 Uiso 1 1 calc R
C9 C 1.11456(15) 0.76191(15) 0.26516(10) 0.0293(2) Uani 1 1 d .
H9A H 1.0812 0.6436 0.2406 0.044 Uiso 1 1 calc R
H9B H 1.1929 0.7987 0.3365 0.044 Uiso 1 1 calc R
H9C H 1.1712 0.7952 0.2138 0.044 Uiso 1 1 calc R
C8 C 0.59045(16) 0.49208(15) -0.19014(9) 0.0297(2) Uani 1 1 d .
H8A H 0.4856 0.4459 -0.1744 0.045 Uiso 1 1 calc R
H8B H 0.6168 0.4126 -0.2509 0.045 Uiso 1 1 calc R
H8C H 0.5748 0.5899 -0.2089 0.045 Uiso 1 1 calc R
C7 C 0.29158(16) 0.86136(18) 0.02226(10) 0.0340(3) Uani 1 1 d .
H7A H 0.3312 0.8882 -0.0370 0.051 Uiso 1 1 calc R
H7B H 0.2037 0.9231 0.0420 0.051 Uiso 1 1 calc R
H7C H 0.2439 0.7452 -0.0008 0.051 Uiso 1 1 calc R
Cl1 Cl 0.82460(4) 1.41569(4) 0.27362(3) 0.03871(9) Uani 1 1 d .
Cl2 Cl 1.20782(4) 1.44869(4) 0.41863(3) 0.03896(9) 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'
Cl Cl 0.1484 0.1585 '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
Si2 C12 Si1 120.49(6)
C2 C1 C6 115.30(9)
C2 C1 Si1 125.57(8)
C6 C1 Si1 118.94(8)
C2 O1 C7 117.97(9)
C11 Si1 C10 108.25(7)
C11 Si1 C12 107.02(6)
C10 Si1 C12 107.72(6)
C11 Si1 C1 113.96(5)
C10 Si1 C1 107.94(6)
C12 Si1 C1 111.74(5)
O1 C2 C3 121.11(10)
O1 C2 C1 115.74(9)
C3 C2 C1 123.14(10)
C4 O2 C8 117.06(9)
C12 Si2 C13 116.75(6)
C12 Si2 Cl2 109.33(5)
C13 Si2 Cl2 107.34(5)
C12 Si2 Cl1 109.82(5)
C13 Si2 Cl1 107.47(5)
Cl2 Si2 Cl1 105.52(4)
C4 C3 C2 118.46(10)
C6 O3 C9 117.97(9)
O2 C4 C3 123.41(10)
O2 C4 C5 115.30(10)
C3 C4 C5 121.29(10)
O3 C6 C5 122.38(10)
O3 C6 C1 114.18(9)
C5 C6 C1 123.44(10)
C6 C5 C4 118.37(10)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C13 Si2 1.8601(13)
C12 Si2 1.8345(13)
C12 Si1 1.8895(13)
C11 Si1 1.8680(13)
C10 Si1 1.8760(13)
C1 C2 1.4017(15)
C1 C6 1.4130(15)
C1 Si1 1.8899(12)
O1 C2 1.3694(13)
O1 C7 1.4262(14)
C2 C3 1.4003(15)
O2 C4 1.3668(13)
O2 C8 1.4286(15)
Si2 Cl2 2.0614(7)
Si2 Cl1 2.0652(7)
C3 C4 1.3900(15)
O3 C6 1.3697(13)
O3 C9 1.4256(14)
C4 C5 1.3907(16)
C6 C5 1.3897(16)
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
Si2 C12 Si1 C11 -75.23(8)
Si2 C12 Si1 C10 168.56(7)
Si2 C12 Si1 C1 50.17(8)
C2 C1 Si1 C11 -13.34(12)
C6 C1 Si1 C11 172.01(9)
C2 C1 Si1 C10 106.93(10)
C6 C1 Si1 C10 -67.72(10)
C2 C1 Si1 C12 -134.81(10)
C6 C1 Si1 C12 50.54(10)
C7 O1 C2 C3 -0.26(17)
C7 O1 C2 C1 -179.39(11)
C6 C1 C2 O1 178.14(10)
Si1 C1 C2 O1 3.31(15)
C6 C1 C2 C3 -0.97(16)
Si1 C1 C2 C3 -175.79(9)
Si1 C12 Si2 C13 -64.15(9)
Si1 C12 Si2 Cl2 173.80(5)
Si1 C12 Si2 Cl1 58.47(7)
O1 C2 C3 C4 -178.51(10)
C1 C2 C3 C4 0.54(17)
C8 O2 C4 C3 0.21(16)
C8 O2 C4 C5 179.80(10)
C2 C3 C4 O2 179.52(10)
C2 C3 C4 C5 -0.05(17)
C9 O3 C6 C5 2.65(16)
C9 O3 C6 C1 -177.58(10)
C2 C1 C6 O3 -178.80(9)
Si1 C1 C6 O3 -3.61(13)
C2 C1 C6 C5 0.97(16)
Si1 C1 C6 C5 176.16(9)
O3 C6 C5 C4 179.21(10)
C1 C6 C5 C4 -0.54(17)
O2 C4 C5 C6 -179.55(10)
C3 C4 C5 C6 0.05(17)
