#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:41:55 +0100 (Sat 26 de Mar de 2016) $
#$Revision: 180311 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/25/7152581.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_7152581
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         'C23 H24 O2'
_chemical_formula_sum            'C23 H24 O2'
_chemical_formula_weight         332.42
_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                 98.9270(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.5765(9)
_cell_length_b                   11.1441(5)
_cell_length_c                   8.1245(4)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.18
_cell_measurement_theta_min      2.72
_cell_volume                     1840.43(15)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_device_type  Bruker-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  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0230
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            38468
_diffrn_reflns_theta_full        33.14
_diffrn_reflns_theta_max         33.14
_diffrn_reflns_theta_min         1.00
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  .7465
_exptl_absorpt_correction_T_min  .6280
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker-SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       flat_plate
_exptl_crystal_F_000             712
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .10
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     231
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0553
_refine_ls_R_factor_gt           0.0422
_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)+(0.0565P)²+0.5356P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1216
_reflns_number_gt                5507
_reflns_number_total             6772
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2ob25989c.txt
_cod_data_source_block           glu11k
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7152581
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 0.62420(5) -0.06038(9) 0.47594(11) 0.02171(17) Uani 1 1 d .
H1A H 0.6120 0.0194 0.4306 0.033 Uiso 1 1 calc R
H1B H 0.5889 -0.1174 0.4373 0.033 Uiso 1 1 calc R
H1C H 0.6648 -0.0866 0.4379 0.033 Uiso 1 1 calc R
C2 C 0.65644(5) -0.17939(8) 0.73640(12) 0.02212(17) Uani 1 1 d .
H2A H 0.6979 -0.2020 0.6995 0.033 Uiso 1 1 calc R
H2B H 0.6224 -0.2384 0.6956 0.033 Uiso 1 1 calc R
H2C H 0.6626 -0.1771 0.8584 0.033 Uiso 1 1 calc R
C3 C 0.54586(5) 0.19667(8) 0.84853(11) 0.02055(17) Uani 1 1 d .
H3A H 0.5622 0.2581 0.9310 0.031 Uiso 1 1 calc R
H3B H 0.5022 0.1700 0.8668 0.031 Uiso 1 1 calc R
H3C H 0.5430 0.2304 0.7362 0.031 Uiso 1 1 calc R
C4 C 0.59886(5) 0.03949(9) 1.04487(11) 0.02049(17) Uani 1 1 d .
H4A H 0.6257 -0.0335 1.0542 0.031 Uiso 1 1 calc R
H4B H 0.5549 0.0206 1.0696 0.031 Uiso 1 1 calc R
H4C H 0.6196 0.0995 1.1243 0.031 Uiso 1 1 calc R
C5 C 0.66148(4) 0.12269(7) 0.83378(10) 0.01434(14) Uani 1 1 d .
C6 C 0.68604(4) 0.03948(7) 0.73083(9) 0.01385(14) Uani 1 1 d .
C7 C 0.75043(4) 0.04795(8) 0.69858(10) 0.01557(15) Uani 1 1 d .
H7 H 0.7675 -0.0105 0.6317 0.019 Uiso 1 1 calc R
C8 C 0.78956(4) 0.14431(8) 0.76659(10) 0.01643(15) Uani 1 1 d .
C9 C 0.76390(4) 0.22962(8) 0.86682(11) 0.01809(16) Uani 1 1 d .
H9 H 0.7903 0.2956 0.9106 0.022 Uiso 1 1 calc R
C10 C 0.70026(4) 0.21814(8) 0.90238(10) 0.01745(16) Uani 1 1 d .
H10 H 0.6834 0.2746 0.9725 0.021 Uiso 1 1 calc R
C11 C 0.85504(4) 0.16110(8) 0.73122(11) 0.01884(16) Uani 1 1 d .
C12 C 0.90889(4) 0.18387(8) 0.69833(11) 0.01955(16) Uani 1 1 d .
C13 C 0.97125(4) 0.21484(8) 0.65232(10) 0.01727(16) Uani 1 1 d .
C14 C 1.01560(4) 0.12558(8) 0.62143(11) 0.02013(17) Uani 1 1 d .
H14 H 1.0055 0.0436 0.6372 0.024 Uiso 1 1 calc R
C15 C 1.07439(4) 0.15602(9) 0.56777(11) 0.01994(16) Uani 1 1 d .
H15 H 1.1039 0.0948 0.5450 0.024 Uiso 1 1 calc R
C16 C 1.09011(4) 0.27603(8) 0.54735(10) 0.01718(15) Uani 1 1 d .
C17 C 1.04696(4) 0.36582(8) 0.58309(12) 0.02014(17) Uani 1 1 d .
H17 H 1.0582 0.4478 0.5726 0.024 Uiso 1 1 calc R
C18 C 0.98771(4) 0.33540(8) 0.63395(12) 0.02048(17) Uani 1 1 d .
H18 H 0.9582 0.3967 0.6564 0.025 Uiso 1 1 calc R
C19 C 1.15214(4) 0.30418(9) 0.48173(11) 0.01932(16) Uani 1 1 d .
C20 C 1.21214(5) 0.45376(10) 0.36557(13) 0.0278(2) Uani 1 1 d .
H20A H 1.2518 0.4398 0.4469 0.042 Uiso 1 1 calc R
H20B H 1.2093 0.5390 0.3354 0.042 Uiso 1 1 calc R
H20C H 1.2141 0.4055 0.2657 0.042 Uiso 1 1 calc R
C01 C 0.63506(4) -0.05501(7) 0.66701(10) 0.01515(15) Uani 1 1 d .
C02 C 0.59320(4) 0.08955(8) 0.86666(10) 0.01537(15) Uani 1 1 d .
C03 C 0.57231(4) -0.00778(8) 0.73164(11) 0.01972(16) Uani 1 1 d .
H22A H 0.5414 0.0270 0.6383 0.024 Uiso 1 1 calc R
H22B H 0.5498 -0.0747 0.7799 0.024 Uiso 1 1 calc R
O1 O 1.19459(4) 0.23146(7) 0.46719(10) 0.02840(16) Uani 1 1 d .
O2 O 1.15481(3) 0.41989(7) 0.43749(9) 0.02276(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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C01 C1 H1A 109.5
C01 C1 H1B 109.5
H1A C1 H1B 109.5
C01 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
C01 C2 H2A 109.5
C01 C2 H2B 109.5
H2A C2 H2B 109.5
C01 C2 H2C 109.5
H2A C2 H2C 109.5
H2B C2 H2C 109.5
C02 C3 H3A 109.5
C02 C3 H3B 109.5
H3A C3 H3B 109.5
C02 C3 H3C 109.5
H3A C3 H3C 109.5
H3B C3 H3C 109.5
C02 C4 H4A 109.5
C02 C4 H4B 109.5
H4A C4 H4B 109.5
C02 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C10 C5 C6 120.61(8)
C10 C5 C02 127.19(7)
C6 C5 C02 112.06(7)
C7 C6 C5 120.75(7)
C7 C6 C01 127.52(7)
C5 C6 C01 111.72(7)
C6 C7 C8 118.83(8)
C6 C7 H7 120.6
C8 C7 H7 120.6
C7 C8 C9 120.07(8)
C7 C8 C11 121.40(8)
C9 C8 C11 118.49(8)
C10 C9 C8 120.56(8)
C10 C9 H9 119.7
C8 C9 H9 119.7
C9 C10 C5 119.12(8)
C9 C10 H10 120.4
C5 C10 H10 120.4
C12 C11 C8 175.16(10)
C11 C12 C13 177.01(10)
C14 C13 C18 119.24(8)
C14 C13 C12 120.73(8)
C18 C13 C12 120.02(8)
C15 C14 C13 120.42(8)
C15 C14 H14 119.8
C13 C14 H14 119.8
C14 C15 C16 120.11(8)
C14 C15 H15 119.9
C16 C15 H15 119.9
C15 C16 C17 119.74(8)
C15 C16 C19 118.20(8)
C17 C16 C19 122.02(8)
C18 C17 C16 120.16(8)
C18 C17 H17 119.9
C16 C17 H17 119.9
C17 C18 C13 120.28(8)
C17 C18 H18 119.9
C13 C18 H18 119.9
O1 C19 O2 123.84(8)
O1 C19 C16 124.38(9)
O2 C19 C16 111.77(8)
O2 C20 H20A 109.5
O2 C20 H20B 109.5
H20A C20 H20B 109.5
O2 C20 H20C 109.5
H20A C20 H20C 109.5
H20B C20 H20C 109.5
C6 C01 C2 110.92(7)
C6 C01 C1 110.89(7)
C2 C01 C1 108.95(7)
C6 C01 C03 102.42(6)
C2 C01 C03 112.73(7)
C1 C01 C03 110.83(7)
C5 C02 C3 112.69(7)
C5 C02 C4 108.49(7)
C3 C02 C4 109.07(7)
C5 C02 C03 102.00(6)
C3 C02 C03 111.92(7)
C4 C02 C03 112.52(7)
C02 C03 C01 108.68(7)
C02 C03 H22A 110.0
C01 C03 H22A 110.0
C02 C03 H22B 110.0
C01 C03 H22B 110.0
H22A C03 H22B 108.3
C19 O2 C20 115.41(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C01 1.5348(12)
C1 H1A 0.9800
C1 H1B 0.9800
C1 H1C 0.9800
C2 C01 1.5348(12)
C2 H2A 0.9800
C2 H2B 0.9800
C2 H2C 0.9800
C3 C02 1.5334(12)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C02 1.5391(12)
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 C10 1.3931(12)
C5 C6 1.3949(11)
C5 C02 1.5159(11)
C6 C7 1.3931(11)
C6 C01 1.5196(11)
C7 C8 1.4031(12)
C7 H7 0.9500
C8 C9 1.4069(12)
C8 C11 1.4328(12)
C9 C10 1.3899(12)
C9 H9 0.9500
C10 H10 0.9500
C11 C12 1.2064(12)
C12 C13 1.4334(12)
C13 C14 1.3987(13)
C13 C18 1.3992(13)
C14 C15 1.3899(12)
C14 H14 0.9500
C15 C16 1.3919(13)
C15 H15 0.9500
C16 C17 1.3979(13)
C16 C19 1.4909(12)
C17 C18 1.3887(12)
C17 H17 0.9500
C18 H18 0.9500
C19 O1 1.2106(12)
C19 O2 1.3420(12)
C20 O2 1.4454(11)
C20 H20A 0.9800
C20 H20B 0.9800
C20 H20C 0.9800
C01 C03 1.5589(12)
C02 C03 1.5551(12)
C03 H22A 0.9900
C03 H22B 0.9900
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 1.98(12)
C02 C5 C6 C7 -173.98(7)
C10 C5 C6 C01 -178.70(7)
C02 C5 C6 C01 5.34(10)
C5 C6 C7 C8 -2.30(12)
C01 C6 C7 C8 178.49(8)
C6 C7 C8 C9 0.65(12)
C6 C7 C8 C11 -176.92(8)
C7 C8 C9 C10 1.36(13)
C11 C8 C9 C10 179.00(8)
C8 C9 C10 C5 -1.71(13)
C6 C5 C10 C9 0.06(12)
C02 C5 C10 C9 175.35(8)
C7 C8 C11 C12 129.0(11)
C9 C8 C11 C12 -48.6(11)
C8 C11 C12 C13 -36(3)
C11 C12 C13 C14 -127.2(19)
C11 C12 C13 C18 51(2)
C18 C13 C14 C15 -2.11(13)
C12 C13 C14 C15 176.36(8)
C13 C14 C15 C16 1.20(14)
C14 C15 C16 C17 0.84(13)
C14 C15 C16 C19 -177.09(8)
C15 C16 C17 C18 -1.94(13)
C19 C16 C17 C18 175.91(8)
C16 C17 C18 C13 1.01(14)
C14 C13 C18 C17 1.00(13)
C12 C13 C18 C17 -177.48(8)
C15 C16 C19 O1 -11.09(13)
C17 C16 C19 O1 171.04(9)
C15 C16 C19 O2 167.74(8)
C17 C16 C19 O2 -10.14(12)
C7 C6 C01 C2 64.92(11)
C5 C6 C01 C2 -114.35(8)
C7 C6 C01 C1 -56.28(11)
C5 C6 C01 C1 124.45(8)
C7 C6 C01 C03 -174.56(8)
C5 C6 C01 C03 6.17(9)
C10 C5 C02 C3 49.91(11)
C6 C5 C02 C3 -134.46(8)
C10 C5 C02 C4 -70.97(11)
C6 C5 C02 C4 104.66(8)
C10 C5 C02 C03 170.08(8)
C6 C5 C02 C03 -14.29(9)
C5 C02 C03 C01 17.77(9)
C3 C02 C03 C01 138.48(7)
C4 C02 C03 C01 -98.28(8)
C6 C01 C03 C02 -15.02(9)
C2 C01 C03 C02 104.24(8)
C1 C01 C03 C02 -133.34(8)
O1 C19 O2 C20 1.44(13)
C16 C19 O2 C20 -177.40(7)
