A Total Synthesis of (±)-3-O-Demethylmacronine through Rearrangement of a Precursor Embodying the Haemanthidine Alkaloid Framework.
Ma, Xiang; Gao, Nadia; Banwell, Martin G.; Carr, Paul D.; Willis, Anthony C.; The Journal of organic chemistry 82 (2017) 4336–4341; doi:10.1021/acs.joc.7b00340

data_4032668
_publ_section_title
;
 A Total Synthesis of (+-)-3-O-Demethylmacronine through Rearrangement of
 a Precursor Embodying the Haemanthidine Alkaloid Framework.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4336
_journal_page_last               4341
_journal_paper_doi               10.1021/acs.joc.7b00340
_journal_volume                  82
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_compound_source        local
_chemical_formula_moiety         'C24 H31 N O4 Si'
_chemical_formula_sum            'C24 H31 N O4 Si'
_chemical_formula_weight         425.60
_space_group_IT_number           43
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_creation_date             14-11-26
_audit_creation_method           CRYSTALS_ver_14.40
_audit_update_record
;
2014-11-26 - Report on C24 H31 N O4 Si 
             by Anthony C. Willis
             for   Nadia Gao and Martin Banwell

2014-11-26 - passes checkcif tests with minor warnings  
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   34.4510(4)
_cell_length_b                   27.1978(4)
_cell_length_c                   9.5573(1)
_cell_measurement_reflns_used    15169
_cell_measurement_temperature    150
_cell_measurement_theta_max      72
_cell_measurement_theta_min      4
_cell_volume                     8955.11(19)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2014)'
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
;
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2014)'
_computing_molecular_graphics    'PLATON (Spek, 2008)'
_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      150
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'Supernova (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.044
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            34843
_diffrn_reflns_theta_full        72.298
_diffrn_reflns_theta_max         72.298
_diffrn_reflns_theta_min         4.142
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.168
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33d (release 23-04-2014 CrysAlis171 .NET)
(compiled Apr 23 2014,17:37:27)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.263
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             3648
_exptl_crystal_size_max          0.247
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.36
_refine_ls_abs_structure_details 'Flack (1983), 1366 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3717
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0338
_refine_ls_shift/su_max          0.0014452
_refine_ls_shift/su_mean         0.0000907
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[\s^2^(F^2^) + ( 0.06P)^2^ +12.65P] 
 ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0891
_refine_ls_wR_factor_gt          0.0884
_refine_ls_wR_factor_ref         0.0891
_reflns_limit_h_max              42
_reflns_limit_h_min              0
_reflns_limit_k_max              33
_reflns_limit_k_min              0
_reflns_limit_l_max              9
_reflns_limit_l_min              -11
_reflns_number_gt                3632
_reflns_number_total             3717
_reflns_threshold_expression     I>2.0\s(I)
_oxford_diffrn_Wilson_B_factor   1.84
_oxford_diffrn_Wilson_scale      0.79
_oxford_refine_ls_r_factor_ref   0.0347
_oxford_refine_ls_scale          1.116(4)
_oxford_reflns_number_all        3717
_oxford_reflns_threshold_expression_ref I>-10.0\s(I)
_oxford_structure_analysis_title 'Z:\ban1459SN\Tony_ban1459SN_data At 17:41 on'
_cod_data_source_file            jo7b00340_si_001.cif
_cod_data_source_block           ban1459SN
_cod_depositor_comments          'Adding full bibliography for 4032668.cif.'
_cod_original_sg_symbol_Hall     'F 2 -2d '
_cod_original_sg_symbol_H-M      'F d d 2 '
_cod_database_code               4032668
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   2,X'S) H   (  21,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) H   (  52,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) H   ( 203,X'S) 
RIDE C   (  25,X'S) H   ( 251,X'S) H   ( 252,X'S) H   ( 253,X'S) 
RIDE C   (  26,X'S) H   ( 261,X'S) H   ( 262,X'S) H   ( 263,X'S) 
RIDE C   (  28,X'S) H   ( 281,X'S) H   ( 282,X'S) H   ( 283,X'S) 
RIDE C   (  29,X'S) H   ( 291,X'S) H   ( 292,X'S) H   ( 293,X'S) 
RIDE C   (  30,X'S) H   ( 301,X'S) H   ( 302,X'S) H   ( 303,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                                                                             
;