Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles Rearrangement Reaction.
Lan, Ping; Jackson, Colin J.; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 79 (2014) 6759–6764; doi:10.1021/jo501255c

data_4029677
_publ_section_title
;
 Synthesis of a D-Ring Isomer of Galanthamine via a Radical-Based Smiles
 Rearrangement Reaction.
;
_journal_issue                   14
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6759
_journal_page_last               6764
_journal_paper_doi               10.1021/jo501255c
_journal_volume                  79
_journal_year                    2014
_chemical_compound_source        local
_chemical_formula_moiety         'C20 H29 Br O4 Si'
_chemical_formula_sum            'C20 H29 Br O4 Si'
_chemical_formula_weight         441.44
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-05-19
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-05-19 - Report on C20 H29 Br O4 Si
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2014-05-20 - passes checkcif tests
;
_cell_angle_alpha                90
_cell_angle_beta                 97.5273(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.0338(2)
_cell_length_b                   7.9720(1)
_cell_length_c                   23.2133(4)
_cell_measurement_reflns_used    76753
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     2207.74(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       ' \f and \w scans with CCD '
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.065
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            43047
_diffrn_reflns_theta_full        27.437
_diffrn_reflns_theta_max         27.437
_diffrn_reflns_theta_min         2.615
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.936
_exptl_absorpt_correction_T_max  0.874
_exptl_absorpt_correction_T_min  0.539
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.57
_refine_diff_density_min         -0.62
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         5031
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.0091961
_refine_ls_shift/su_mean         0.0015559
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 1.19P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0870
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0870
_reflns_limit_h_max              15
_reflns_limit_h_min              -15
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              30
_reflns_limit_l_min              0
_reflns_number_gt                3991
_reflns_number_total             5031
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.53
_oxford_diffrn_Wilson_scale      4.96
_oxford_refine_ls_r_factor_ref   0.0500
_oxford_refine_ls_scale          0.5052(7)
_oxford_reflns_number_all        5031
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1408early At 9:53 on 19/ 5'
_cod_data_source_file            jo501255c_si_003.cif
_cod_data_source_block           ban1409
_cod_depositor_comments
'Adding full bibliography for 4029675--4029677.cif.'
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4029677
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,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   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,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) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;