Studies on the Photochemical Rearrangements of Enantiomerically Pure, Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones.
Yan, Qiao; Bolte, Benoit; Bai, Yuhua; Banwell, Martin G.; Willis, Anthony C.; Carr, Paul D.; The Journal of organic chemistry 82 (2017) 8008–8022; doi:10.1021/acs.joc.7b01243

data_4032660
_publ_section_title
;
 Studies on the Photochemical Rearrangements of Enantiomerically Pure,
 Polysubstituted, and Variously Annulated Bicyclo[2.2.2]octenones.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8008
_journal_page_last               8022
_journal_paper_doi               10.1021/acs.joc.7b01243
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C14 H26 O2 Si'
_chemical_formula_sum            'C14 H26 O2 Si'
_chemical_formula_weight         254.45
_space_group_IT_number           18
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2 2ab'
_symmetry_space_group_name_H-M   'P 21 21 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_audit_creation_date             16-05-10
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2016-05-10 - Report on C14 H26 O2 Si 
             by Anthony C. Willis
             for   Qiao Yan and Martin Banwell

2016-05-10 - details of refinement in _refine_special_details below

2016-05-10 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.3637(1)
_cell_length_b                   14.1093(1)
_cell_length_c                   12.0122(1)
_cell_measurement_reflns_used    46950
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     3112.35(4)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2015)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2015)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            61855
_diffrn_reflns_theta_full        72.467
_diffrn_reflns_theta_max         72.467
_diffrn_reflns_theta_min         3.951
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.248
_exptl_absorpt_correction_T_max  0.79
_exptl_absorpt_correction_T_min  0.68
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET)
(compiled Feb 9 2015,16:26:32)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1120.000
_exptl_crystal_size_max          0.398
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.186
_refine_diff_density_max         0.21
_refine_diff_density_min         -0.22
_refine_ls_abs_structure_details 'Flack (1983), 2703 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.003(14)
_refine_ls_extinction_coef       65(7)
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_refine_ls_goodness_of_fit_ref   1.0100
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     385
_refine_ls_number_reflns         6159
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0250
_refine_ls_R_factor_gt           0.0248
_refine_ls_shift/su_max          0.0021003
_refine_ls_shift/su_mean         0.0001299
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.46P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0668
_refine_ls_wR_factor_gt          0.0666
_refine_ls_wR_factor_ref         0.0668
_reflns_limit_h_max              22
_reflns_limit_h_min              -22
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                6101
_reflns_number_total             6159
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      0.05
_oxford_refine_ls_r_factor_ref   0.0250
_oxford_refine_ls_scale          4.86(5)
_oxford_reflns_number_all        6159
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title
'Z:\ban1629SN\Tony_ban1629SN_data At 12:45 on'
_cod_data_source_file            jo7b01243_si_002.cif
_cod_data_source_block           ban1629SN_compound_13
_cod_depositor_comments
;
The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Other' changed to 'other'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4032648--4032665.cif.
;
_cod_original_sg_symbol_H-M      'P 21 21 2 '
_cod_database_code               4032660
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, SI(1,U'S) 
CONT SI(2,U'S,OCC) UNTIL SI(102) 
CONT O(1,U'S) UNTIL C(28) 
CONT C(29,U'S,OCC) UNTIL C(134) 
CONT ENANTIO EXTPARAM H(1,X'S) UNTIL H(4) 
EQUIV SI(2,OCC) SI(102,OCC) C(29,OCC) UNTIL C(134) 
WEIGHT -1 SI(102,OCC) C(129,OCC) UNTIL C(134) 
RIDE C ( 1,X'S) H( 11,X'S) 
RIDE C ( 3,X'S) H( 31,X'S) 
RIDE C ( 4,X'S) H( 41,X'S) 
RIDE C ( 5,X'S) H( 51,X'S) 
RIDE C ( 6,X'S) H( 61,X'S) H( 62,X'S) 
RIDE C ( 7,X'S) H( 71,X'S) 
RIDE C ( 8,X'S) H( 81,X'S) H( 82,X'S) H( 83,X'S) 
RIDE C ( 9,X'S) H( 91,X'S) H( 92,X'S) H( 93,X'S) 
RIDE C ( 10,X'S) H( 101,X'S) H( 102,X'S) H( 103,X'S) 
RIDE C ( 12,X'S) H( 121,X'S) H( 122,X'S) H( 123,X'S) 
RIDE C ( 13,X'S) H( 131,X'S) H( 132,X'S) H( 133,X'S) 
RIDE C ( 14,X'S) H( 141,X'S) H( 142,X'S) H( 143,X'S) 
RIDE C ( 21,X'S) H( 211,X'S) 
RIDE C ( 23,X'S) H( 231,X'S) 
RIDE C ( 24,X'S) H( 241,X'S) 
RIDE C ( 25,X'S) H( 251,X'S) 
RIDE C ( 26,X'S) H( 261,X'S) H( 262,X'S) 
RIDE C ( 27,X'S) H( 271,X'S) 
RIDE C ( 28,X'S) H( 281,X'S) H( 282,X'S) H( 283,X'S) 
RIDE C ( 29,X'S) H( 291,X'S) H( 292,X'S) H( 293,X'S) 
RIDE C ( 30,X'S) H( 301,X'S) H( 302,X'S) H( 303,X'S) 
RIDE C ( 32,X'S) H( 321,X'S) H( 322,X'S) H( 323,X'S) 
RIDE C ( 33,X'S) H( 331,X'S) H( 332,X'S) H( 333,X'S) 
RIDE C ( 34,X'S) H( 341,X'S) H( 342,X'S) H( 343,X'S) 
RIDE C ( 129,X'S) H( 1291,X'S) H( 1292,X'S) H( 1293,X'S) 
RIDE C ( 130,X'S) H( 1301,X'S) H( 1302,X'S) H( 1303,X'S) 
RIDE C ( 132,X'S) H( 1321,X'S) H( 1322,X'S) H( 1323,X'S) 
RIDE C ( 133,X'S) H( 1331,X'S) H( 1332,X'S) H( 1333,X'S) 
RIDE C ( 134,X'S) H( 1341,X'S) H( 1342,X'S) H( 1343,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
U(IJ) 0.0, .02 = C(129) TO C(33) 
U(IJ) 0.0, .002 = C(130) TO C(29) 
U(IJ) 0.0, .02 = C(132) TO C(32) 
U(IJ) 0.0, .02 = C(133) TO C(34) 
U(IJ) 0.0, .02 = C(134) TO C(30) 
REM 
DIST 0.0, .02 = MEAN O(2) TO H(1), O(2) TO H(2) 
CONT                 O(4) TO H(3), O(4) TO H(4) 
ANGLE 109, 2 = C(3) TO O(2) TO H(1), C(3) TO O(2) TO H(2) 
ANGLE 109, 2 = C(23) TO O(4) TO H(3), C(23) TO O(4) TO H(4) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;