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_4033912
_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         'C15 H18 Br N'
_chemical_formula_sum            'C15 H18 Br N'
_chemical_formula_weight         292.22
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             12-02-28
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-02-28- Report on C15 H18 Br N
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2012-02-29 - passes checkcif tests with few warnings

;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2756(2)
_cell_length_b                   11.1263(4)
_cell_length_c                   14.6850(5)
_cell_measurement_reflns_used    10164
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1352.15(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)'
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_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
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_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
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_diffrn_reflns_theta_max         27.445
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_exptl_absorpt_process_details
;
via Gaussian method (Coppens, 1970) implemented in maXus (2000)
;
_exptl_crystal_colour            colourless
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_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
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_exptl_crystal_size_max          0.440
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_refine_ls_abs_structure_details 'Flack (1983), 1301 Friedel-pairs'
_refine_ls_abs_structure_Flack   -0.008(9)
_refine_ls_extinction_method     None
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_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3077
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_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.0029944
_refine_ls_shift/su_mean         0.0001869
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.03P)^2^ + 0.32P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0636
_refine_ls_wR_factor_gt          0.0604
_refine_ls_wR_factor_ref         0.0636
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2694
_reflns_number_total             3078
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   4.12
_oxford_diffrn_Wilson_scale      1.20
_oxford_refine_ls_r_factor_ref   0.0366
_oxford_refine_ls_scale          0.924(2)
_oxford_reflns_number_all        3077
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '2281533 both'
_cod_data_source_file            jo9b00018_si_009.cif
_cod_data_source_block           ban1204
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Orthorhombic' was changed
to 'orthorhombic' 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 21 21 21 '
_cod_database_code               4033912
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL BR   (   17 ) 
CONT H    (   21 ,X'S)  UNTIL H    (   71 ) 
CONT ENANTIO 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;