#------------------------------------------------------------------------------
#$Date: 2016-03-26 15:41:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180311 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/25/7152584.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_7152584
loop_
_publ_author_name
'Gluyas, Josef B. G.'
'Burschka, Christian'
'Dörrich, Steffen'
'Vallet, Judith'
'Gronemeyer, Hinrich'
'Tacke, Reinhold'
_publ_section_title
;
 Disila-analogues of the synthetic retinoids EC23 and TTNN: synthesis,
 structure and biological evaluation.
;
_journal_issue                   34
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6914
_journal_page_last               6929
_journal_paper_doi               10.1039/c2ob25989c
_journal_volume                  10
_journal_year                    2012
_chemical_formula_moiety         'C13 H24 O Si3'
_chemical_formula_sum            'C13 H24 O Si3'
_chemical_formula_weight         280.59
_chemical_name_systematic
;
?
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 91.347(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   6.2270(8)
_cell_length_b                   10.0764(18)
_cell_length_c                   14.0512(19)
_cell_measurement_reflns_used    3052
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.05
_cell_measurement_theta_min      7.2
_cell_volume                     881.4(2)
_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 0.922
_diffrn_measured_fraction_theta_max 0.922
_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  0.0605
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11609
_diffrn_reflns_theta_full        29.52
_diffrn_reflns_theta_max         29.52
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.256
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.057
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          .5
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0433
_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)+(0.0778P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1094
_refine_ls_wR_factor_ref         0.1232
_reflns_number_gt                3705
_reflns_number_total             4562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25989c.txt
_cod_data_source_block           glu07f
_cod_original_sg_symbol_H-M      P21
_cod_database_code               7152584
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5280(6) 0.0889(3) 0.2988(2) 0.0534(8) Uani 1 1 d . . .
H1A H 0.5851 -0.0003 0.2882 0.080 Uiso 1 1 calc R . .
H1B H 0.4596 0.0921 0.3609 0.080 Uiso 1 1 calc R . .
H1C H 0.6455 0.1536 0.2976 0.080 Uiso 1 1 calc R . .
C2 C 0.1161(6) 0.0006(3) 0.2014(3) 0.0545(8) Uani 1 1 d . . .
H2A H 0.0105 0.0221 0.1509 0.082 Uiso 1 1 calc R . .
H2B H 0.0448 -0.0019 0.2628 0.082 Uiso 1 1 calc R . .
H2C H 0.1801 -0.0862 0.1886 0.082 Uiso 1 1 calc R . .
C3 C 0.7405(5) 0.3574(3) 0.0461(2) 0.0438(6) Uani 1 1 d . A .
H3A H 0.8052 0.3572 0.1104 0.066 Uiso 1 1 calc R . .
H3B H 0.7389 0.4482 0.0211 0.066 Uiso 1 1 calc R . .
H3C H 0.8248 0.3005 0.0046 0.066 Uiso 1 1 calc R . .
C4 C 0.3438(5) 0.2916(3) -0.07051(18) 0.0430(6) Uani 1 1 d . A .
H4A H 0.4419 0.2465 -0.1134 0.064 Uiso 1 1 calc R . .
H4B H 0.3200 0.3829 -0.0925 0.064 Uiso 1 1 calc R . .
H4C H 0.2064 0.2442 -0.0702 0.064 Uiso 1 1 calc R . .
C5 C 0.2881(4) 0.3851(2) 0.14027(15) 0.0289(5) Uani 1 1 d . A .
C6 C 0.2203(4) 0.3022(2) 0.21707(15) 0.0284(4) Uani 1 1 d . . .
C7 C 0.0836(5) 0.3552(2) 0.28909(16) 0.0317(5) Uani 1 1 d . A .
H7 H 0.0375 0.2983 0.3385 0.038 Uiso 1 1 calc R . .
C8 C 0.0167(5) 0.4875(2) 0.28856(17) 0.0336(5) Uani 1 1 d . . .
C9 C 0.0874(5) 0.5672(3) 0.21174(17) 0.0361(6) Uani 1 1 d . A .
H9 H 0.0447 0.6576 0.2092 0.043 Uiso 1 1 calc R . .
C10 C 0.2185(4) 0.5175(2) 0.13901(18) 0.0337(5) Uani 1 1 d . . .
H10 H 0.2598 0.5744 0.0888 0.040 Uiso 1 1 calc R A .
Si3 Si -0.15925(14) 0.55432(7) 0.38888(5) 0.0396(2) Uani 0.429(18) 1 d PD A 1
C11 C -0.396(2) 0.4516(15) 0.4055(10) 0.066(3) Uani 0.429(18) 1 d PDU A 1
H11A H -0.3535 0.3579 0.4065 0.099 Uiso 0.429(18) 1 calc PR A 1
H11B H -0.4991 0.4669 0.3531 0.099 Uiso 0.429(18) 1 calc PR A 1
H11C H -0.4616 0.4746 0.4660 0.099 Uiso 0.429(18) 1 calc PR A 1
C12 C -0.217(3) 0.7331(10) 0.3671(9) 0.073(3) Uani 0.429(18) 1 d PDU A 1
H12A H -0.3211 0.7646 0.4132 0.110 Uiso 0.429(18) 1 calc PR A 1
H12B H -0.2766 0.7445 0.3024 0.110 Uiso 0.429(18) 1 calc PR A 1
H12C H -0.0839 0.7843 0.3741 0.110 Uiso 0.429(18) 1 calc PR A 1
C13 C 0.0158(17) 0.5478(14) 0.5013(6) 0.051(2) Uani 0.429(18) 1 d PDU A 1
H13A H 0.1526 0.5926 0.4899 0.076 Uiso 0.429(18) 1 calc PR A 1
H13B H 0.0431 0.4551 0.5187 0.076 Uiso 0.429(18) 1 calc PR A 1
H13C H -0.0579 0.5925 0.5532 0.076 Uiso 0.429(18) 1 calc PR A 1
Si3B Si -0.15925(14) 0.55432(7) 0.38888(5) 0.0396(2) Uani 0.571(18) 1 d PD A 2
C11B C -0.3576(15) 0.4213(9) 0.4309(8) 0.060(2) Uani 0.571(18) 1 d PDU A 2
H11D H -0.2774 0.3444 0.4556 0.090 Uiso 0.571(18) 1 calc PR A 2
H11E H -0.4504 0.3935 0.3772 0.090 Uiso 0.571(18) 1 calc PR A 2
H11F H -0.4459 0.4581 0.4813 0.090 Uiso 0.571(18) 1 calc PR A 2
C12B C -0.332(2) 0.6958(10) 0.3463(6) 0.073(3) Uani 0.571(18) 1 d PDU A 2
H12D H -0.4020 0.7369 0.4008 0.110 Uiso 0.571(18) 1 calc PR A 2
H12E H -0.4423 0.6625 0.3013 0.110 Uiso 0.571(18) 1 calc PR A 2
H12F H -0.2433 0.7618 0.3146 0.110 Uiso 0.571(18) 1 calc PR A 2
C13B C 0.0098(17) 0.6054(15) 0.4874(7) 0.076(3) Uani 0.571(18) 1 d PDU A 2
H13D H 0.1271 0.6605 0.4642 0.114 Uiso 0.571(18) 1 calc PR A 2
H13E H 0.0696 0.5268 0.5195 0.114 Uiso 0.571(18) 1 calc PR A 2
H13F H -0.0750 0.6566 0.5324 0.114 Uiso 0.571(18) 1 calc PR A 2
O1 O 0.4542(3) 0.14372(17) 0.09986(12) 0.0363(4) Uani 1 1 d . A .
Si1 Si 0.32936(12) 0.12890(6) 0.20494(4) 0.03207(16) Uani 1 1 d . . .
Si2 Si 0.46214(11) 0.29401(6) 0.05059(4) 0.02921(15) 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
C10 C5 C6 117.8(2)
C10 C5 Si2 128.81(18)
C6 C5 Si2 113.37(17)
C5 C6 C7 120.1(2)
C5 C6 Si1 111.01(17)
C7 C6 Si1 128.91(18)
C8 C7 C6 122.1(2)
C7 C8 C9 116.4(2)
C7 C8 Si3 120.28(19)
C9 C8 Si3 123.30(19)
C10 C9 C8 122.9(2)
C5 C10 C9 120.7(2)
C11 Si3 C12 114.7(6)
C11 Si3 C13 108.9(5)
C12 Si3 C13 106.0(6)
C11 Si3 C8 111.8(4)
C12 Si3 C8 109.2(4)
C13 Si3 C8 105.7(4)
Si2 O1 Si1 117.50(10)
O1 Si1 C1 109.37(13)
O1 Si1 C2 112.45(12)
C1 Si1 C2 109.72(17)
O1 Si1 C6 99.87(9)
C1 Si1 C6 112.18(12)
C2 Si1 C6 112.93(15)
O1 Si2 C4 110.94(13)
O1 Si2 C3 111.42(12)
C4 Si2 C3 109.19(13)
O1 Si2 C5 98.00(9)
C4 Si2 C5 113.23(12)
C3 Si2 C5 113.70(12)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 Si1 1.832(3)
C2 Si1 1.853(3)
C3 Si2 1.850(3)
C4 Si2 1.838(3)
C5 C10 1.403(3)
C5 C6 1.436(3)
C5 Si2 1.915(2)
C6 C7 1.440(3)
C6 Si1 1.882(3)
C7 C8 1.397(3)
C8 C9 1.423(4)
C8 Si3 1.927(3)
C9 C10 1.414(4)
Si3 C11 1.819(11)
Si3 C12 1.861(9)
Si3 C13 1.899(8)
O1 Si2 1.6664(19)
O1 Si1 1.6913(18)
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 C5 C6 C7 0.6(3)
Si2 C5 C6 C7 -178.36(18)
C10 C5 C6 Si1 179.64(18)
Si2 C5 C6 Si1 0.7(2)
C5 C6 C7 C8 -1.5(4)
Si1 C6 C7 C8 179.6(2)
C6 C7 C8 C9 1.2(4)
C6 C7 C8 Si3 -178.15(19)
C7 C8 C9 C10 0.0(4)
Si3 C8 C9 C10 179.3(2)
C6 C5 C10 C9 0.5(4)
Si2 C5 C10 C9 179.30(18)
C8 C9 C10 C5 -0.8(4)
C7 C8 Si3 C11 -52.4(6)
C9 C8 Si3 C11 128.2(6)
C7 C8 Si3 C12 179.5(7)
C9 C8 Si3 C12 0.2(7)
C7 C8 Si3 C13 65.9(5)
C9 C8 Si3 C13 -113.4(5)
Si2 O1 Si1 C1 -112.47(15)
Si2 O1 Si1 C2 125.38(17)
Si2 O1 Si1 C6 5.40(14)
C5 C6 Si1 O1 -3.42(18)
C7 C6 Si1 O1 175.5(2)
C5 C6 Si1 C1 112.3(2)
C7 C6 Si1 C1 -68.7(3)
C5 C6 Si1 C2 -123.05(19)
C7 C6 Si1 C2 55.9(3)
Si1 O1 Si2 C4 -123.67(14)
Si1 O1 Si2 C3 114.45(15)
Si1 O1 Si2 C5 -4.97(14)
C10 C5 Si2 O1 -176.5(2)
C6 C5 Si2 O1 2.37(19)
C10 C5 Si2 C4 -59.5(3)
C6 C5 Si2 C4 119.32(19)
C10 C5 Si2 C3 65.9(3)
C6 C5 Si2 C3 -115.30(19)
