#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:51:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178585 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/96/4069636.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_4069636
loop_
_publ_author_name
'Metz, Stefan'
'Nätscher, Jennifer B.'
'Burschka, Christian'
'Götz, Kathrin'
'Kaupp, Martin'
'Kraft, Philip'
'Tacke, Reinhold'
_publ_section_title
;
 Disila-Phantolide and Derivatives: Synthesis and Olfactory
 Characterization of Silicon-Containing Derivatives of the Musk Odorant
 Phantolide§
;
_journal_issue                   16
_journal_name_full               Organometallics
_journal_page_first              4700
_journal_paper_doi               10.1021/om9003219
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C12 H18 O2 Si2'
_chemical_formula_sum            'C12 H18 O2 Si2'
_chemical_formula_weight         250.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 94.99(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   14.234(3)
_cell_length_b                   8.4211(17)
_cell_length_c                   12.165(2)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      25.8
_cell_measurement_theta_min      8.55
_cell_volume                     1452.6(5)
_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 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0534
_diffrn_reflns_av_sigmaI/netI    0.0296
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            19782
_diffrn_reflns_theta_full        28.98
_diffrn_reflns_theta_max         28.98
_diffrn_reflns_theta_min         2.81
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       blocks
_exptl_crystal_F_000             536
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .4
_exptl_crystal_size_min          .3
_refine_diff_density_max         0.349
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.055
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0582
_refine_ls_R_factor_gt           0.0487
_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)+(0.0765P)²+0.5121P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1302
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                3131
_reflns_number_total             3782
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om9003219_si_002.cif
_cod_data_source_block           Compound11
_cod_original_cell_volume        1452.7(5)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4069636
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
C1 C 0.26708(15) 1.3038(2) 0.57276(16) 0.0440(4) Uani 1 1 d .
H1A H 0.3214 1.3751 0.5842 0.066 Uiso 1 1 calc R
H1B H 0.2160 1.3426 0.6147 0.066 Uiso 1 1 calc R
H1C H 0.2455 1.3005 0.4941 0.066 Uiso 1 1 calc R
C2 C 0.34156(18) 1.1040(3) 0.76964(17) 0.0535(5) Uani 1 1 d .
H2A H 0.3679 1.0000 0.7914 0.080 Uiso 1 1 calc R
H2B H 0.2879 1.1273 0.8122 0.080 Uiso 1 1 calc R
H2C H 0.3900 1.1858 0.7841 0.080 Uiso 1 1 calc R
C5 C 0.36413(18) 0.9076(3) 0.32410(17) 0.0533(5) Uani 1 1 d .
H5A H 0.3271 1.0030 0.3041 0.080 Uiso 1 1 calc R
H5B H 0.3378 0.8170 0.2812 0.080 Uiso 1 1 calc R
H5C H 0.4297 0.9243 0.3081 0.080 Uiso 1 1 calc R
C6 C 0.44096(14) 0.7028(2) 0.51862(17) 0.0439(4) Uani 1 1 d .
H6A H 0.5058 0.7328 0.5065 0.066 Uiso 1 1 calc R
H6B H 0.4234 0.6069 0.4760 0.066 Uiso 1 1 calc R
H6C H 0.4367 0.6818 0.5973 0.066 Uiso 1 1 calc R
C7 C 0.23629(12) 0.8316(2) 0.51294(13) 0.0326(3) Uani 1 1 d .
C8 C 0.20745(11) 0.94866(19) 0.58644(13) 0.0312(3) Uani 1 1 d .
C9 C 0.11819(12) 0.9386(2) 0.62631(14) 0.0346(3) Uani 1 1 d .
H9 H 0.0988 1.0177 0.6752 0.041 Uiso 1 1 calc R
C10 C 0.05736(12) 0.8129(2) 0.59474(15) 0.0373(4) Uani 1 1 d .
C11 C 0.08636(14) 0.6982(2) 0.52130(16) 0.0425(4) Uani 1 1 d .
H11 H 0.0453 0.6129 0.4993 0.051 Uiso 1 1 calc R
C12 C 0.17395(14) 0.7074(2) 0.48040(16) 0.0402(4) Uani 1 1 d .
H12 H 0.1921 0.6293 0.4300 0.048 Uiso 1 1 calc R
C13 C -0.03697(13) 0.7951(3) 0.63959(16) 0.0440(4) Uani 1 1 d .
C14 C -0.07694(15) 0.9333(3) 0.6975(2) 0.0578(6) Uani 1 1 d .
H14A H -0.1422 0.9100 0.7120 0.087 Uiso 1 1 calc R
H14B H -0.0756 1.0281 0.6509 0.087 Uiso 1 1 calc R
H14C H -0.0392 0.9523 0.7675 0.087 Uiso 1 1 calc R
O1 O 0.38442(9) 1.02906(16) 0.54690(12) 0.0443(3) Uani 1 1 d .
O2 O -0.07986(11) 0.6698(2) 0.62970(15) 0.0610(4) Uani 1 1 d .
Si1 Si 0.30169(3) 1.10196(5) 0.62044(4) 0.03127(14) Uani 1 1 d .
Si2 Si 0.35988(3) 0.86663(6) 0.47355(4) 0.03326(14) 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
C12 C7 C8 119.02(15)
C12 C7 Si2 128.66(13)
C8 C7 Si2 112.31(12)
C9 C8 C7 119.86(15)
C9 C8 Si1 128.03(13)
C7 C8 Si1 112.10(12)
C10 C9 C8 120.57(16)
C9 C10 C11 119.09(16)
C9 C10 C13 121.82(17)
C11 C10 C13 119.06(17)
C12 C11 C10 120.99(16)
C11 C12 C7 120.45(16)
O2 C13 C14 120.73(19)
O2 C13 C10 120.4(2)
C14 C13 C10 118.84(17)
Si2 O1 Si1 118.09(8)
O1 Si1 C1 110.70(9)
O1 Si1 C2 111.13(10)
C1 Si1 C2 110.43(10)
O1 Si1 C8 98.84(7)
C1 Si1 C8 113.35(9)
C2 Si1 C8 111.92(9)
O1 Si1 Si2 30.91(5)
C1 Si1 Si2 121.90(6)
C2 Si1 Si2 122.78(8)
C8 Si1 Si2 67.93(5)
O1 Si2 C6 111.08(9)
O1 Si2 C5 110.57(10)
C6 Si2 C5 110.85(10)
O1 Si2 C7 98.64(7)
C6 Si2 C7 112.29(8)
C5 Si2 C7 112.85(10)
O1 Si2 Si1 30.99(5)
C6 Si2 Si1 122.84(7)
C5 Si2 Si1 121.52(8)
C7 Si2 Si1 67.65(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Si1 1.849(2)
C2 Si1 1.854(2)
C5 Si2 1.857(2)
C6 Si2 1.851(2)
C7 C12 1.406(2)
C7 C8 1.416(2)
C7 Si2 1.8863(18)
C8 C9 1.401(2)
C8 Si1 1.8817(17)
C9 C10 1.400(2)
C10 C11 1.402(3)
C10 C13 1.500(2)
C11 C12 1.384(3)
C13 O2 1.220(2)
C13 C14 1.498(3)
O1 Si2 1.6538(14)
O1 Si1 1.6575(14)
Si1 Si2 2.8397(8)
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
C12 C7 C8 C9 0.6(3)
Si2 C7 C8 C9 -178.45(13)
C12 C7 C8 Si1 179.33(13)
Si2 C7 C8 Si1 0.29(16)
C7 C8 C9 C10 0.5(3)
Si1 C8 C9 C10 -178.03(13)
C8 C9 C10 C11 -0.9(3)
C8 C9 C10 C13 177.45(16)
C9 C10 C11 C12 0.3(3)
C13 C10 C11 C12 -178.12(17)
C10 C11 C12 C7 0.8(3)
C8 C7 C12 C11 -1.2(3)
Si2 C7 C12 C11 177.65(14)
C9 C10 C13 O2 -164.62(19)
C11 C10 C13 O2 13.8(3)
C9 C10 C13 C14 14.8(3)
C11 C10 C13 C14 -166.81(19)
Si2 O1 Si1 C1 -117.93(11)
Si2 O1 Si1 C2 118.97(12)
Si2 O1 Si1 C8 1.25(12)
C9 C8 Si1 O1 177.73(16)
C7 C8 Si1 O1 -0.88(14)
C9 C8 Si1 C1 -65.09(18)
C7 C8 Si1 C1 116.30(13)
C9 C8 Si1 C2 60.61(19)
C7 C8 Si1 C2 -118.00(14)
C9 C8 Si1 Si2 178.42(17)
C7 C8 Si1 Si2 -0.19(10)
Si1 O1 Si2 C6 -119.13(11)
Si1 O1 Si2 C5 117.35(12)
Si1 O1 Si2 C7 -1.11(12)
C12 C7 Si2 O1 -178.50(17)
C8 C7 Si2 O1 0.43(14)
C12 C7 Si2 C6 -61.40(19)
C8 C7 Si2 C6 117.53(13)
C12 C7 Si2 C5 64.77(19)
C8 C7 Si2 C5 -116.30(14)
C12 C7 Si2 Si1 -179.12(18)
C8 C7 Si2 Si1 -0.19(10)
C1 Si1 Si2 O1 76.77(14)
C2 Si1 Si2 O1 -76.07(15)
C8 Si1 Si2 O1 -178.67(13)
O1 Si1 Si2 C6 75.94(14)
C1 Si1 Si2 C6 152.71(11)
C2 Si1 Si2 C6 -0.14(12)
C8 Si1 Si2 C6 -102.73(10)
O1 Si1 Si2 C5 -77.28(15)
C1 Si1 Si2 C5 -0.50(13)
C2 Si1 Si2 C5 -153.35(14)
C8 Si1 Si2 C5 104.06(12)
O1 Si1 Si2 C7 178.81(12)
C1 Si1 Si2 C7 -104.42(10)
C2 Si1 Si2 C7 102.74(11)
C8 Si1 Si2 C7 0.14(8)
