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_4033908
_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         'C25 H27 N O7 S'
_chemical_formula_sum            'C25 H27 N O7 S'
_chemical_formula_weight         485.56
_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   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             13-03-20
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2013-03-20 - Report on C25 H27 N O7 S
            by Anthony C. Willis
            for  Ping Lan and Martin Banwell

2013-03-20 - racemic

2013-03-20 - passes checkcif tests

;
_cell_angle_alpha                110.082(2)
_cell_angle_beta                 97.268(2)
_cell_angle_gamma                100.494(2)
_cell_formula_units_Z            2
_cell_length_a                   9.5083(4)
_cell_length_b                   10.2316(3)
_cell_length_c                   13.3051(6)
_cell_measurement_reflns_used    33114
_cell_measurement_temperature    200
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.6
_cell_volume                     1170.04(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 0.995
_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  0.059
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24262
_diffrn_reflns_theta_full        27.549
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_min         2.715
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.963
_exptl_absorpt_correction_T_min  0.943
_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    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.310
_refine_diff_density_max         0.55
_refine_diff_density_min         -0.55
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9931
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
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_refine_ls_number_reflns         5375
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0656
_refine_ls_R_factor_gt           0.0522
_refine_ls_shift/su_max          0.0004990
_refine_ls_shift/su_mean         0.0000280
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.08P)^2^ + 0.70P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1459
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1459
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4303
_reflns_number_total             5375
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   3.13
_oxford_diffrn_Wilson_scale      0.88
_oxford_refine_ls_r_factor_ref   0.0656
_oxford_refine_ls_scale          1.099(5)
_oxford_reflns_number_all        5375
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'ban1312 At 16:42 on 19/ 3'
_cod_data_source_file            jo9b00018_si_015.cif
_cod_data_source_block           ban1312
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4033908
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
RIDE C   (   1,X'S) H   (  11,X'S) 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  82,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  15,X'S) H   ( 152,X'S) H   ( 151,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 203,X'S) H   ( 202,X'S) H   ( 201,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) 
RIDE C   (  30,X'S) H   ( 302,X'S) H   ( 301,X'S) H   ( 303,X'S) 
RIDE C   (  34,X'S) H   ( 342,X'S) H   ( 341,X'S) H   ( 343,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;