#------------------------------------------------------------------------------
#$Date: 2016-03-21 14:14:30 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178712 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/23/4082386.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_4082386
loop_
_publ_author_name
'Fischer, Markus'
'Burschka, Christian'
'Tacke, Reinhold'
_publ_section_title
;
 Synthesis of 4-Silacyclohexan-1-ones and (4-Silacyclohexan-1-yl)amines
 Containing the Silicon Protecting Groups MOP (4-Methoxyphenyl), DMOP
 (2,4-Dimethoxyphenyl), or TMOP (2,4,6-Trimethoxyphenyl): Versatile Si-
 and C-Functional Building Blocks for Synthesis
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1020
_journal_paper_doi               10.1021/om401208y
_journal_volume                  33
_journal_year                    2014
_chemical_formula_moiety         'C20 H24 O4 Si'
_chemical_formula_sum            'C20 H24 O4 Si'
_chemical_formula_weight         356.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.3403(19)
_cell_length_b                   23.911(5)
_cell_length_c                   8.7619(18)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.35
_cell_measurement_theta_min      7.05
_cell_volume                     1956.8(7)
_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, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  image_plate_Stoe-IPDS
_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  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0303
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            13369
_diffrn_reflns_theta_full        29.12
_diffrn_reflns_theta_max         29.12
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         4265
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0514P)²+0.3592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0901
_refine_ls_wR_factor_ref         0.0950
_reflns_number_gt                3744
_reflns_number_total             4265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om401208y_si_002.cif
_cod_data_source_block           fis23b_6
_cod_original_sg_symbol_H-M      Pna21
_cod_database_code               4082386
loop_
_symmetry_equiv_pos_as_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'
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 0.13227(17) 0.66680(7) 0.9605(3) 0.0299(4) Uani 1 1 d .
H1A H 0.1196 0.6789 0.8533 0.036 Uiso 1 1 calc R
H1B H 0.0425 0.6486 0.9941 0.036 Uiso 1 1 calc R
C2 C 0.1620(2) 0.71833(8) 1.0618(3) 0.0381(4) Uani 1 1 d .
H2A H 0.2472 0.7381 1.0220 0.046 Uiso 1 1 calc R
H2B H 0.0796 0.7442 1.0548 0.046 Uiso 1 1 calc R
C3 C 0.1871(2) 0.70384(9) 1.2277(3) 0.0381(4) Uani 1 1 d .
C4 C 0.3161(2) 0.66784(9) 1.2643(3) 0.0397(5) Uani 1 1 d .
H4A H 0.3200 0.6618 1.3760 0.048 Uiso 1 1 calc R
H4B H 0.4039 0.6883 1.2343 0.048 Uiso 1 1 calc R
C5 C 0.3159(2) 0.61043(8) 1.1843(2) 0.0323(4) Uani 1 1 d .
H5A H 0.2404 0.5868 1.2304 0.039 Uiso 1 1 calc R
H5B H 0.4091 0.5919 1.2025 0.039 Uiso 1 1 calc R
C6 C 0.24003(16) 0.54485(7) 0.8861(2) 0.0234(3) Uani 1 1 d .
C7 C 0.31694(16) 0.49686(7) 0.9282(2) 0.0235(3) Uani 1 1 d .
C8 C 0.28984(16) 0.44394(7) 0.8657(2) 0.0261(3) Uani 1 1 d .
H8 H 0.3434 0.4122 0.8970 0.031 Uiso 1 1 calc R
C9 C 0.18246(17) 0.43928(8) 0.7567(2) 0.0287(4) Uani 1 1 d .
C10 C 0.10763(18) 0.48602(8) 0.7046(2) 0.0330(4) Uani 1 1 d .
H10 H 0.0368 0.4825 0.6274 0.040 Uiso 1 1 calc R
C11 C 0.13921(17) 0.53783(8) 0.7685(2) 0.0279(4) Uani 1 1 d .
C12 C 0.5164(2) 0.46078(9) 1.0693(3) 0.0433(5) Uani 1 1 d .
H12A H 0.4633 0.4314 1.1228 0.065 Uiso 1 1 calc R
H12B H 0.5940 0.4745 1.1347 0.065 Uiso 1 1 calc R
H12C H 0.5569 0.4456 0.9748 0.065 Uiso 1 1 calc R
C13 C 0.2071(2) 0.33963(9) 0.7497(3) 0.0419(5) Uani 1 1 d .
H13A H 0.3098 0.3405 0.7271 0.063 Uiso 1 1 calc R
H13B H 0.1636 0.3070 0.7003 0.063 Uiso 1 1 calc R
H13C H 0.1930 0.3372 0.8603 0.063 Uiso 1 1 calc R
C14 C -0.0084(4) 0.58438(14) 0.5857(4) 0.0895(14) Uani 1 1 d .
H14A H 0.0452 0.5662 0.5034 0.134 Uiso 1 1 calc R
H14B H -0.0341 0.6225 0.5546 0.134 Uiso 1 1 calc R
H14C H -0.0958 0.5630 0.6069 0.134 Uiso 1 1 calc R
C15 C 0.44708(18) 0.64454(8) 0.8722(2) 0.0286(4) Uani 1 1 d .
C16 C 0.58574(19) 0.62720(10) 0.9128(3) 0.0394(5) Uani 1 1 d .
H16 H 0.5979 0.6017 0.9951 0.047 Uiso 1 1 calc R
C17 C 0.7057(2) 0.64672(12) 0.8345(3) 0.0523(7) Uani 1 1 d .
H17 H 0.7985 0.6344 0.8632 0.063 Uiso 1 1 calc R
C18 C 0.6899(2) 0.68392(11) 0.7154(3) 0.0540(7) Uani 1 1 d .
H18 H 0.7719 0.6973 0.6627 0.065 Uiso 1 1 calc R
C19 C 0.5542(3) 0.70195(10) 0.6724(3) 0.0507(6) Uani 1 1 d .
H19 H 0.5431 0.7275 0.5903 0.061 Uiso 1 1 calc R
C20 C 0.4341(2) 0.68211(9) 0.7511(3) 0.0394(5) Uani 1 1 d .
H20 H 0.3415 0.6945 0.7214 0.047 Uiso 1 1 calc R
O1 O 0.42243(14) 0.50560(6) 1.03369(18) 0.0350(3) Uani 1 1 d .
O2 O 0.14144(15) 0.38942(6) 0.6935(2) 0.0410(4) Uani 1 1 d .
O3 O 0.07743(16) 0.58654(6) 0.7190(2) 0.0466(4) Uani 1 1 d .
O4 O 0.10890(19) 0.72157(8) 1.3277(2) 0.0557(5) Uani 1 1 d .
Si Si 0.28402(4) 0.615105(17) 0.97187(6) 0.02242(10) 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C2 C1 Si 110.98(13)
C3 C2 C1 113.43(17)
O4 C3 C2 121.2(2)
O4 C3 C4 121.5(2)
C2 C3 C4 117.21(18)
C3 C4 C5 114.11(17)
C4 C5 Si 113.32(14)
C7 C6 C11 115.98(15)
C7 C6 Si 120.81(12)
C11 C6 Si 122.98(13)
O1 C7 C8 122.15(15)
O1 C7 C6 114.95(15)
C8 C7 C6 122.89(15)
C9 C8 C7 118.11(16)
O2 C9 C8 123.33(17)
O2 C9 C10 115.18(16)
C8 C9 C10 121.48(17)
C11 C10 C9 118.42(16)
O3 C11 C10 122.71(16)
O3 C11 C6 114.37(16)
C10 C11 C6 122.89(16)
C20 C15 C16 117.57(18)
C20 C15 Si 121.37(14)
C16 C15 Si 120.99(16)
C17 C16 C15 121.1(2)
C18 C17 C16 120.2(2)
C17 C18 C19 120.2(2)
C18 C19 C20 119.5(2)
C15 C20 C19 121.5(2)
C7 O1 C12 118.60(15)
C9 O2 C13 117.84(17)
C11 O3 C14 117.92(18)
C1 Si C6 113.56(8)
C1 Si C5 102.10(9)
C6 Si C5 111.99(8)
C1 Si C15 109.71(9)
C6 Si C15 108.84(8)
C5 Si C15 110.51(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.544(3)
C1 Si 1.8834(16)
C2 C3 1.512(3)
C3 O4 1.217(3)
C3 C4 1.515(3)
C4 C5 1.541(3)
C5 Si 1.888(2)
C6 C7 1.403(2)
C6 C11 1.406(2)
C6 Si 1.8857(18)
C7 O1 1.367(2)
C7 C8 1.402(2)
C8 C9 1.390(3)
C9 O2 1.369(2)
C9 C10 1.395(3)
C10 C11 1.391(3)
C11 O3 1.370(2)
C12 O1 1.420(2)
C13 O2 1.427(3)
C14 O3 1.418(3)
C15 C20 1.395(3)
C15 C16 1.406(3)
C15 Si 1.8916(18)
C16 C17 1.395(3)
C17 C18 1.379(4)
C18 C19 1.391(4)
C19 C20 1.400(3)
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
Si C1 C2 C3 -57.5(2)
C1 C2 C3 O4 -118.8(2)
C1 C2 C3 C4 63.0(2)
O4 C3 C4 C5 123.0(2)
C2 C3 C4 C5 -58.8(2)
C3 C4 C5 Si 50.8(2)
C11 C6 C7 O1 174.83(16)
Si C6 C7 O1 0.2(2)
C11 C6 C7 C8 -4.2(3)
Si C6 C7 C8 -178.87(13)
O1 C7 C8 C9 -178.61(17)
C6 C7 C8 C9 0.4(3)
C7 C8 C9 O2 -176.49(17)
C7 C8 C9 C10 3.0(3)
O2 C9 C10 C11 177.28(18)
C8 C9 C10 C11 -2.3(3)
C9 C10 C11 O3 176.19(19)
C9 C10 C11 C6 -2.0(3)
C7 C6 C11 O3 -173.24(16)
Si C6 C11 O3 1.3(2)
C7 C6 C11 C10 5.0(3)
Si C6 C11 C10 179.55(15)
C20 C15 C16 C17 -0.2(3)
Si C15 C16 C17 176.78(18)
C15 C16 C17 C18 0.4(4)
C16 C17 C18 C19 -0.3(4)
C17 C18 C19 C20 0.1(4)
C16 C15 C20 C19 0.0(3)
Si C15 C20 C19 -176.96(18)
C18 C19 C20 C15 0.0(4)
C8 C7 O1 C12 6.4(3)
C6 C7 O1 C12 -172.64(18)
C8 C9 O2 C13 3.8(3)
C10 C9 O2 C13 -175.76(18)
C10 C11 O3 C14 -7.8(4)
C6 C11 O3 C14 170.5(3)
C2 C1 Si C6 167.72(14)
C2 C1 Si C5 46.97(16)
C2 C1 Si C15 -70.26(17)
C7 C6 Si C1 -158.26(14)
C11 C6 Si C1 27.50(18)
C7 C6 Si C5 -43.25(16)
C11 C6 Si C5 142.51(15)
C7 C6 Si C15 79.23(15)
C11 C6 Si C15 -95.01(16)
C4 C5 Si C1 -44.33(15)
C4 C5 Si C6 -166.15(13)
C4 C5 Si C15 72.32(16)
C20 C15 Si C1 -28.87(19)
C16 C15 Si C1 154.22(16)
C20 C15 Si C6 95.93(17)
C16 C15 Si C6 -80.97(17)
C20 C15 Si C5 -140.70(17)
C16 C15 Si C5 42.39(18)
