#------------------------------------------------------------------------------
#$Date: 2017-10-13 02:32:00 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201954 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/50/53/1505315.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_1505315
loop_
_publ_author_name
'Shen, Ruichao'
'Corey, E. J.'
_publ_section_title
;
 Studies of the stereochemistry of [2+2]-photocycloaddition reactions of
 2-cyclohexenones with olefins.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1057
_journal_page_last               1059
_journal_paper_doi               10.1021/ol063092r
_journal_volume                  9
_journal_year                    2007
_chemical_formula_sum            'C24 H22 O Si'
_chemical_formula_weight         354.51
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_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                   9.635(2)
_cell_length_b                   10.304(2)
_cell_length_c                   19.145(4)
_cell_measurement_reflns_used    986
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.90
_cell_volume                     1900.7(7)
_computing_cell_refinement       'SMART (BRUKER, V5.625, 2001)'
_computing_data_collection       'ASTRO (BRUKER, V5.007, 1997)'
_computing_data_reduction        'SAINT (BRUKER, V6.22, 2001)'
_computing_molecular_graphics    'SHELXTL (BRUKER, 2000, V6.1)'
_computing_publication_material  'XCIF (Sheldrick and BRUKER, 1997, V5.1)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      193(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker CCD'
_diffrn_measurement_method       'ω, 0.3 deg'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10009
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         2.13
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_correction_T_min  0.9790
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     323
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0392
_refine_ls_shift/su_max          0.054
_refine_ls_shift/su_mean         0.011
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0561P)²+0.6135P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1005
_refine_ls_wR_factor_ref         0.1012
_reflns_number_gt                3269
_reflns_number_total             3352
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol063092rsi20061221_035222.cif
_cod_data_source_block           ejc113t
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1505315
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
Si1 Si 0.39711(6) 0.01178(6) 0.18315(3) 0.02369(16) Uani 1 1 d
O1 O 0.3896(2) -0.1290(2) 0.04046(9) 0.0465(5) Uani 1 1 d
C1 C 0.3154(2) -0.1502(2) 0.15897(12) 0.0267(5) Uani 1 1 d
H1 H 0.381(3) -0.215(2) 0.1729(12) 0.027(6) Uiso 1 1 d
C2 C 0.3045(3) -0.1720(2) 0.08072(13) 0.0352(6) Uani 1 1 d
C3 C 0.1872(3) -0.2515(3) 0.05580(16) 0.0439(7) Uani 1 1 d
H2 H 0.177(4) -0.260(4) 0.006(2) 0.073(11) Uiso 1 1 d
C4 C 0.0993(4) -0.3095(3) 0.09809(17) 0.0482(7) Uani 1 1 d
H3 H 0.031(3) -0.363(3) 0.0803(16) 0.050(8) Uiso 1 1 d
C5 C 0.1051(3) -0.2977(3) 0.17487(16) 0.0465(7) Uani 1 1 d
H5 H 0.164(3) -0.375(3) 0.1957(16) 0.050(8) Uiso 1 1 d
H4 H 0.012(3) -0.304(3) 0.1934(14) 0.041(7) Uiso 1 1 d
C6 C 0.1753(3) -0.1713(3) 0.19614(14) 0.0366(6) Uani 1 1 d
H6 H 0.117(3) -0.097(2) 0.1855(12) 0.027(6) Uiso 1 1 d
H7 H 0.188(3) -0.171(3) 0.2445(14) 0.030(6) Uiso 1 1 d
C7 C 0.4046(2) 0.0176(2) 0.28177(10) 0.0260(4) Uani 1 1 d
C8 C 0.5319(2) 0.0011(2) 0.31531(11) 0.0306(5) Uani 1 1 d
H8 H 0.612(3) -0.005(3) 0.2850(13) 0.039(6) Uiso 1 1 d
C9 C 0.5429(3) 0.0003(3) 0.38789(12) 0.0381(5) Uani 1 1 d
H9 H 0.632(3) -0.017(3) 0.4077(14) 0.052(8) Uiso 1 1 d
C10 C 0.4263(3) 0.0157(3) 0.42798(12) 0.0416(6) Uani 1 1 d
H10 H 0.434(3) 0.015(3) 0.4789(14) 0.042(7) Uiso 1 1 d
C11 C 0.2980(3) 0.0312(3) 0.39674(13) 0.0392(6) Uani 1 1 d
H11 H 0.220(3) 0.044(2) 0.4226(13) 0.033(7) Uiso 1 1 d
C12 C 0.2875(2) 0.0319(2) 0.32460(12) 0.0318(5) Uani 1 1 d
H12 H 0.195(3) 0.037(3) 0.3032(13) 0.042(7) Uiso 1 1 d
C13 C 0.2851(2) 0.1474(2) 0.14786(13) 0.0291(5) Uani 1 1 d
C14 C 0.2655(3) 0.1600(3) 0.07633(15) 0.0399(6) Uani 1 1 d
H13 H 0.305(3) 0.102(3) 0.0447(15) 0.046(8) Uiso 1 1 d
C15 C 0.1771(4) 0.2533(3) 0.0490(2) 0.0533(9) Uani 1 1 d
H14 H 0.168(5) 0.264(5) 0.008(3) 0.089(15) Uiso 1 1 d
C16 C 0.1078(4) 0.3365(3) 0.09229(19) 0.0539(8) Uani 1 1 d
H15 H 0.045(4) 0.406(4) 0.0715(18) 0.072(10) Uiso 1 1 d
C17 C 0.1285(3) 0.3284(3) 0.16340(19) 0.0494(8) Uani 1 1 d
H16 H 0.085(3) 0.380(3) 0.1928(14) 0.033(7) Uiso 1 1 d
C18 C 0.2167(3) 0.2352(2) 0.19064(16) 0.0365(6) Uani 1 1 d
H17 H 0.238(3) 0.238(2) 0.2380(13) 0.026(6) Uiso 1 1 d
C19 C 0.5807(2) 0.0254(2) 0.15128(10) 0.0293(5) Uani 1 1 d
C20 C 0.6440(3) 0.1473(3) 0.14846(14) 0.0358(6) Uani 1 1 d
H18 H 0.594(3) 0.222(3) 0.1591(13) 0.036(7) Uiso 1 1 d
C21 C 0.7834(3) 0.1599(3) 0.13063(15) 0.0436(6) Uani 1 1 d
H19 H 0.826(3) 0.252(3) 0.1281(15) 0.051(8) Uiso 1 1 d
C22 C 0.8602(3) 0.0515(3) 0.11496(15) 0.0457(7) Uani 1 1 d
H20 H 0.951(4) 0.064(3) 0.1004(16) 0.060(9) Uiso 1 1 d
C23 C 0.8001(3) -0.0694(3) 0.11632(16) 0.0476(7) Uani 1 1 d
H21 H 0.845(4) -0.148(3) 0.0995(17) 0.060(9) Uiso 1 1 d
C24 C 0.6612(3) -0.0825(3) 0.13506(15) 0.0389(6) Uani 1 1 d
H22 H 0.625(4) -0.162(3) 0.1380(17) 0.059(9) Uiso 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
C19 Si1 C13 111.51(10)
C19 Si1 C7 106.65(9)
C13 Si1 C7 110.82(10)
C19 Si1 C1 112.11(10)
C13 Si1 C1 108.98(10)
C7 Si1 C1 106.64(10)
C2 C1 C6 112.0(2)
C2 C1 Si1 113.50(17)
C6 C1 Si1 111.96(16)
C2 C1 H1 102.5(14)
C6 C1 H1 110.3(14)
Si1 C1 H1 106.0(14)
O1 C2 C3 121.1(2)
O1 C2 C1 121.8(2)
C3 C2 C1 117.0(2)
C4 C3 C2 123.1(3)
C4 C3 H2 120(2)
C2 C3 H2 117(2)
C3 C4 C5 123.4(3)
C3 C4 H3 120.2(19)
C5 C4 H3 116.3(19)
C4 C5 C6 110.7(2)
C4 C5 H5 109.5(17)
C6 C5 H5 107.7(16)
C4 C5 H4 109.0(17)
C6 C5 H4 111.6(17)
H5 C5 H4 108(2)
C5 C6 C1 112.7(2)
C5 C6 H6 111.1(14)
C1 C6 H6 107.5(14)
C5 C6 H7 108.8(17)
C1 C6 H7 110.2(16)
H6 C6 H7 106(2)
C8 C7 C12 116.81(19)
C8 C7 Si1 119.30(16)
C12 C7 Si1 123.83(17)
C9 C8 C7 121.8(2)
C9 C8 H8 122.4(15)
C7 C8 H8 115.7(15)
C10 C9 C8 119.7(2)
C10 C9 H9 122.4(17)
C8 C9 H9 117.8(17)
C9 C10 C11 120.3(2)
C9 C10 H10 119.6(15)
C11 C10 H10 120.2(15)
C10 C11 C12 119.8(2)
C10 C11 H11 121.3(15)
C12 C11 H11 118.8(15)
C11 C12 C7 121.6(2)
C11 C12 H12 118.8(15)
C7 C12 H12 119.5(15)
C14 C13 C18 117.1(2)
C14 C13 Si1 119.97(19)
C18 C13 Si1 122.86(19)
C15 C14 C13 121.4(3)
C15 C14 H13 116.8(18)
C13 C14 H13 121.7(18)
C16 C15 C14 120.4(3)
C16 C15 H14 117(4)
C14 C15 H14 122(4)
C15 C16 C17 119.4(3)
C15 C16 H15 120(2)
C17 C16 H15 121(2)
C16 C17 C18 120.2(3)
C16 C17 H16 121.8(17)
C18 C17 H16 118.0(17)
C17 C18 C13 121.5(3)
C17 C18 H17 119.0(16)
C13 C18 H17 119.2(16)
C24 C19 C20 117.8(2)
C24 C19 Si1 122.6(2)
C20 C19 Si1 119.39(18)
C21 C20 C19 121.0(3)
C21 C20 H18 118.2(17)
C19 C20 H18 120.8(17)
C22 C21 C20 119.8(3)
C22 C21 H19 121.4(17)
C20 C21 H19 118.8(17)
C23 C22 C21 120.4(2)
C23 C22 H20 122(2)
C21 C22 H20 117(2)
C22 C23 C24 119.9(3)
C22 C23 H21 124(2)
C24 C23 H21 115(2)
C19 C24 C23 121.1(3)
C19 C24 H22 120(2)
C23 C24 H22 119(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Si1 C19 1.877(2)
Si1 C13 1.891(2)
Si1 C7 1.890(2)
Si1 C1 1.902(2)
O1 C2 1.209(3)
C1 C2 1.519(3)
C1 C6 1.541(3)
C1 H1 0.96(3)
C2 C3 1.474(4)
C3 C4 1.316(5)
C3 H2 0.97(4)
C4 C5 1.476(4)
C4 H3 0.92(3)
C5 C6 1.523(4)
C5 H5 1.06(3)
C5 H4 0.97(3)
C6 H6 0.97(3)
C6 H7 0.93(3)
C7 C8 1.395(3)
C7 C12 1.402(3)
C8 C9 1.394(3)
C8 H8 0.97(3)
C9 C10 1.370(4)
C9 H9 0.96(3)
C10 C11 1.383(4)
C10 H10 0.98(3)
C11 C12 1.385(3)
C11 H11 0.91(3)
C12 H12 0.98(3)
C13 C14 1.389(4)
C13 C18 1.387(4)
C14 C15 1.386(4)
C14 H13 0.93(3)
C15 C16 1.366(5)
C15 H14 0.79(5)
C16 C17 1.378(5)
C16 H15 1.02(4)
C17 C18 1.384(4)
C17 H16 0.88(3)
C18 H17 0.93(2)
C19 C24 1.390(3)
C19 C20 1.397(4)
C20 C21 1.392(4)
C20 H18 0.93(3)
C21 C22 1.373(4)
C21 H19 1.03(3)
C22 C23 1.375(4)
C22 H20 0.93(3)
C23 C24 1.392(4)
C23 H21 0.98(4)
C24 H22 0.90(4)
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
C19 Si1 C1 C2 -62.3(2)
C13 Si1 C1 C2 61.62(19)
C7 Si1 C1 C2 -178.70(17)
C19 Si1 C1 C6 169.73(17)
C13 Si1 C1 C6 -66.33(19)
C7 Si1 C1 C6 53.4(2)
C6 C1 C2 O1 160.4(2)
Si1 C1 C2 O1 32.4(3)
C6 C1 C2 C3 -21.3(3)
Si1 C1 C2 C3 -149.2(2)
O1 C2 C3 C4 173.9(3)
C1 C2 C3 C4 -4.5(4)
C2 C3 C4 C5 2.4(5)
C3 C4 C5 C6 25.4(4)
C4 C5 C6 C1 -50.3(3)
C2 C1 C6 C5 48.6(3)
Si1 C1 C6 C5 177.38(19)
C19 Si1 C7 C8 -14.0(2)
C13 Si1 C7 C8 -135.58(19)
C1 Si1 C7 C8 105.9(2)
C19 Si1 C7 C12 168.93(19)
C13 Si1 C7 C12 47.4(2)
C1 Si1 C7 C12 -71.1(2)
C12 C7 C8 C9 -0.7(4)
Si1 C7 C8 C9 -177.9(2)
C7 C8 C9 C10 0.1(4)
C8 C9 C10 C11 0.4(4)
C9 C10 C11 C12 -0.4(4)
C10 C11 C12 C7 -0.2(4)
C8 C7 C12 C11 0.7(3)
Si1 C7 C12 C11 177.79(19)
C19 Si1 C13 C14 61.7(2)
C7 Si1 C13 C14 -179.7(2)
C1 Si1 C13 C14 -62.6(2)
C19 Si1 C13 C18 -120.2(2)
C7 Si1 C13 C18 -1.5(2)
C1 Si1 C13 C18 115.5(2)
C18 C13 C14 C15 -2.4(4)
Si1 C13 C14 C15 175.9(2)
C13 C14 C15 C16 0.7(5)
C14 C15 C16 C17 1.2(5)
C15 C16 C17 C18 -1.2(4)
C16 C17 C18 C13 -0.5(4)
C14 C13 C18 C17 2.3(4)
Si1 C13 C18 C17 -175.90(19)
C13 Si1 C19 C24 -143.7(2)
C7 Si1 C19 C24 95.2(2)
C1 Si1 C19 C24 -21.2(2)
C13 Si1 C19 C20 41.2(2)
C7 Si1 C19 C20 -79.9(2)
C1 Si1 C19 C20 163.76(18)
C24 C19 C20 C21 -0.6(4)
Si1 C19 C20 C21 174.7(2)
C19 C20 C21 C22 0.5(4)
C20 C21 C22 C23 0.4(5)
C21 C22 C23 C24 -1.3(5)
C20 C19 C24 C23 -0.3(4)
Si1 C19 C24 C23 -175.4(2)
C22 C23 C24 C19 1.2(5)
loop_
_cod_related_entry_id
_cod_related_entry_code
_cod_related_entry_database
1 21199604 ChemSpider
