Total Synthesis of (±)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane Using a 5- exo- trig Radical Cyclization Reaction to Assemble the C3a-Arylated Perhydroindole Substructure.
Lan, Ping; Banwell, Martin G.; Willis, Anthony C.; The Journal of organic chemistry 83 (2018) 8493–8498; doi:10.1021/acs.joc.8b01088

data_4035605
_publ_section_title
;
 Total Synthesis of (+-)-Crinane from 6,6-Dibromobicyclo[3.1.0]hexane
 Using a 5- exo- trig Radical Cyclization Reaction to Assemble the
 C3a-Arylated Perhydroindole Substructure.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8493
_journal_page_last               8498
_journal_paper_doi               10.1021/acs.joc.8b01088
_journal_volume                  83
_journal_year                    2018
_chemical_compound_source        local
_chemical_formula_moiety         'C16 H20 Cl N O2 +, Cl -'
_chemical_formula_sum            'C16 H20 Cl N O2'
_chemical_formula_weight         293.79
_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             12-08-20
_audit_creation_method           CRYSTALS_ver_14.11
_audit_update_record
;
2012-08-20- Report on C8 H9 Br F3 N O (Batch 2)
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2012-08-20 - passes checkcif tests with few warnings

;
_cell_angle_alpha                111.307(3)
_cell_angle_beta                 101.280(4)
_cell_angle_gamma                92.617(4)
_cell_formula_units_Z            2
_cell_length_a                   7.0293(3)
_cell_length_b                   9.9371(7)
_cell_length_c                   11.3882(8)
_cell_measurement_reflns_used    23663
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     720.83(8)
_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 0.995
_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  0.060
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14467
_diffrn_reflns_theta_full        26.964
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_min         2.979
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_T_min  0.916
_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    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9949
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.0145309
_refine_ls_shift/su_mean         0.0018237
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.28P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1102
_refine_ls_wR_factor_gt          0.0997
_refine_ls_wR_factor_ref         0.1102
_reflns_limit_h_max              8
_reflns_limit_h_min              -9
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2597
_reflns_number_total             3294
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   2.97
_oxford_diffrn_Wilson_scale      0.70
_oxford_refine_ls_r_factor_ref   0.0596
_oxford_refine_ls_scale          1.197(6)
_oxford_reflns_number_all        3294
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title '8201119 ban1227'
_cod_data_source_file            jo8b01088_si_002.cif
_cod_data_source_block           ban1227
_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               4035605
_iucr_refine_instruction_details_constraints
;
BLOCK 
CONT SCALE 
CONT C    (    1 ,X'S,U'S)  UNTIL CL   (   20 ) 
CONT H    (   71 ,X'S)  UNTIL H    (  192 ) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;