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_4033917
_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_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C8 H9 Br F3 N O'
_chemical_formula_sum            'C8 H9 Br F3 N O'
_chemical_formula_weight         272.06
_space_group_IT_number           1
_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             12-06-05
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-06-05- Report on C8 H9 Br F3 N O
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2012-06-05 - passes checkcif tests with few warnings

;
_cell_angle_alpha                101.669(3)
_cell_angle_beta                 91.920(4)
_cell_angle_gamma                107.523(4)
_cell_formula_units_Z            2
_cell_length_a                   5.0260(3)
_cell_length_b                   7.7300(4)
_cell_length_c                   13.7908(8)
_cell_measurement_reflns_used    32748
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     497.80(5)
_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 0.996
_diffrn_measured_fraction_theta_max 0.985
_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  0.063
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9698
_diffrn_reflns_theta_full        27.077
_diffrn_reflns_theta_max         27.629
_diffrn_reflns_theta_min         2.835
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.140
_exptl_absorpt_correction_T_max  0.81
_exptl_absorpt_correction_T_min  0.45
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.815
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             268
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.050
_refine_diff_density_max         2.31
_refine_diff_density_min         -1.58
_refine_ls_abs_structure_details 'Flack (1983), 1939 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9860
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     276
_refine_ls_number_reflns         4224
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0537
_refine_ls_shift/su_max          0.0392522
_refine_ls_shift/su_mean         0.0031295
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.11P)^2^ + 0.36P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1507
_refine_ls_wR_factor_gt          0.1403
_refine_ls_wR_factor_ref         0.1507
_reflns_limit_h_max              6
_reflns_limit_h_min              -5
_reflns_limit_k_max              10
_reflns_limit_k_min              -10
_reflns_limit_l_max              17
_reflns_limit_l_min              -17
_reflns_number_gt                3590
_reflns_number_total             4224
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.14
_oxford_diffrn_Wilson_scale      0.92
_oxford_refine_ls_r_factor_ref   0.0626
_oxford_refine_ls_scale          1.079
_oxford_reflns_number_all        4224
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '6041525 ban1220a'
_cod_data_source_file            jo9b00018_si_008.cif
_cod_data_source_block           ban1220
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_sg_symbol_H-M      'P 1 '
_cod_database_code               4033917
_iucr_refine_instruction_details_constraints
;
BLOCK  X'S, BR(14,U'S) UNTIL BR(34) 
CONT F(11,U'S,OCC) UNTIL F(33) F(111,U[ISO],OCC) UNTIL F(133) 
CONT O(9,U'S) UNTIL C(30) 
SUMFIX ELEMENT SCALES 
EQUIV F(11,OCC) UNTIL F(13) F(111,OCC) UNTIL F(113) 
WEIGHT -1 F(111,OCC) UNTIL F(113) 
EQUIV F(31,OCC) UNTIL F(33) F(131,OCC) UNTIL F(133) 
WEIGHT -1 F(131,OCC) UNTIL F(133) 
EQUIV F(111,U[ISO]) UNTIL F(113) 
EQUIV F(131,U[ISO]) UNTIL F(133) 
RIDE N(7,X'S) H(71,X'S) 
RIDE N(27,X'S) H(271,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) 
RIDE C   (  23,X'S) H   ( 231,X'S) H   ( 232,X'S) 
RIDE C   (  24,X'S) H   ( 241,X'S) H   ( 242,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
DIST 0.0, .02 = MEAN C(10) TO F(111), C(10) TO F(112), C(10) TO F(113) 
DIST 0.0, .02 = MEAN C(30) TO F(131), C(30) TO F(132), C(30) TO F(133) 
ANGLE 0.0, 2. = MEAN F(111) TO C(10) TO F(112), F(111) TO C(10) TO F(113) 
CONT            F(112) TO C(10) TO F(113) 
ANGLE 0.0, 2. = MEAN F(131) TO C(30) TO F(132), F(131) TO C(30) TO F(133) 
CONT            F(132) TO C(30) TO F(133) 
ANGLE 0.0, 2. = MEAN C(8) TO C(10) TO F(111), C(8) TO C(10) TO F(112) 
CONT            C(8) TO C(10) TO F(113) 
ANGLE 0.0, 2. = MEAN C(28) TO C(30) TO F(131), C(28) TO C(30) TO F(132) 
CONT            C(28) TO C(30) TO F(133) 
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;