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_4029676
_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         'C17 H24 N O3 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C23 H26 N4 O10'
_chemical_formula_weight         518.48
_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             13-07-18
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-07-19 - Report on C23 H26 N4 O10
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-07-19 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 97.2592(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.9504(2)
_cell_length_b                   9.5641(2)
_cell_length_c                   21.5400(4)
_cell_measurement_reflns_used    32242
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     2237.82(7)
_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
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.054
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            41573
_diffrn_reflns_theta_full        27.491
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         2.838
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.966
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            'dark yellow'
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.48
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9585
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         5135
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0460
_refine_ls_shift/su_max          0.0120898
_refine_ls_shift/su_mean         0.0006068
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 1.27P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1196
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1196
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              27
_reflns_limit_l_min              0
_reflns_number_gt                3650
_reflns_number_total             5135
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.59
_oxford_diffrn_Wilson_scale      7.19
_oxford_refine_ls_r_factor_ref   0.0742
_oxford_refine_ls_scale          0.4047(6)
_oxford_reflns_number_all        5135
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1350 At 16:16 on 18/7/13'
_cod_data_source_file            jo501255c_si_004.cif
_cod_data_source_block           ban1350
_cod_depositor_comments
'Adding full bibliography for 4029675--4029677.cif.'
_cod_original_sg_symbol_Hall     '-P 2ybc '
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4029676
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL O    (   37 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  331 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;