Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of Crinine and Haemanthamine Alkaloids.
Lan, Ping; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 84 (2019) 3431–3466; doi:10.1021/acs.joc.9b00018

data_4033906
_publ_section_title
;
 Application of Electrocyclic Ring-Opening and Desymmetrizing Nucleophilic
 Trappings of meso-6,6-Dibromobicyclo[3.1.0]hexanes to Total Syntheses of
 Crinine and Haemanthamine Alkaloids.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3431
_journal_page_last               3466
_journal_paper_doi               10.1021/acs.joc.9b00018
_journal_volume                  84
_journal_year                    2019
_chemical_compound_source        local
_chemical_formula_moiety         ' C16 H18 N O4 +, C6 H2 N3 O7 -'
_chemical_formula_sum            'C22 H20 N4 O11'
_chemical_formula_weight         516.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yab'
_space_group_name_H-M_alt        'P 1 21/a 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-03-08
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-03-12 - Report on C23 H24 N4 O12
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-03-12 - racemic

2013-03-12 - passes checkcif tests

;
_cell_angle_alpha                90
_cell_angle_beta                 110.4722(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6279(1)
_cell_length_b                   26.7808(5)
_cell_length_c                   9.8839(2)
_cell_measurement_reflns_used    27329
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3
_cell_volume                     2139.55(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 0.998
_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  0.058
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            35395
_diffrn_reflns_theta_full        27.482
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_min         2.632
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          0.430
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.49
_refine_diff_density_min         -0.52
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9482
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         4899
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0749
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.0054572
_refine_ls_shift/su_mean         0.0004352
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.05P)^2^ + 1.03P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1052
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1052
_reflns_limit_h_max              10
_reflns_limit_h_min              -11
_reflns_limit_k_max              34
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                3417
_reflns_number_total             4899
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.57
_oxford_diffrn_Wilson_scale      8.14
_oxford_refine_ls_r_factor_ref   0.0749
_oxford_refine_ls_scale          0.3827(5)
_oxford_reflns_number_all        4899
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1308 At 15:18 on 8/ 3'
_cod_data_source_file            jo9b00018_si_005.cif
_cod_data_source_block           ban1308
_cod_original_sg_symbol_H-M      'P 1 21/a 1 '
_cod_database_code               4033906
_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    (  401 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;