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_4033907
_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 H15 N O3'
_chemical_formula_sum            'C16 H15 N O3'
_chemical_formula_weight         269.30
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-12-06
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-12-06 - Report on C16 H15 N O3
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2012-12-06 - passes checkcif tests

;
_cell_angle_alpha                88.6579(18)
_cell_angle_beta                 77.6969(14)
_cell_angle_gamma                69.8404(18)
_cell_formula_units_Z            2
_cell_length_a                   7.0347(2)
_cell_length_b                   9.4014(2)
_cell_length_c                   10.0921(3)
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_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     611.26(3)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 2001).'
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_computing_molecular_graphics
; 
ORTEP-II (Johnson 1976) in teXsan (MSC, 1992-1997)
;
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_diffrn_ambient_temperature      200
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.991
_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
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13911
_diffrn_reflns_theta_full        26.705
_diffrn_reflns_theta_max         27.531
_diffrn_reflns_theta_min         3.017
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.970
_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    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.360
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_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         2793
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_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.0002782
_refine_ls_shift/su_mean         0.0000580
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.18P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1030
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.1030
_reflns_limit_h_max              9
_reflns_limit_h_min              -8
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2355
_reflns_number_total             2793
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.37
_oxford_diffrn_Wilson_scale      0.40
_oxford_refine_ls_r_factor_ref   0.0464
_oxford_refine_ls_scale          1.622(12)
_oxford_reflns_number_all        2793
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '12061122 ban1250'
_cod_data_source_file            jo9b00018_si_007.cif
_cod_data_source_block           ban1250
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4033907
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL O    (   20 ) 
CONT H    (   11 ,X'S)  UNTIL H    (  191 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;