Benzoquinone-derived sulfinyl imines as versatile intermediates for alkaloid synthesis: Total synthesis of (–)-3-demethoxyerythratidinone
Chuang, Kangway V.; Navarro, Raul; Reisman, Sarah E.; Chemical Science 2 (2011) 1086–; doi:10.1039/c1sc00095k

data_1515546
_publ_section_title
;
 Benzoquinone-derived sulfinyl imines as versatile intermediates for
 alkaloid synthesis: Total synthesis of (--)-3-demethoxyerythratidinone
;
_journal_issue                   6
_journal_name_full               'Chemical Science'
_journal_page_first              1086
_journal_paper_doi               10.1039/c1sc00095k
_journal_volume                  2
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H18 Br N O2 S'
_chemical_formula_sum            'C12 H18 Br N O2 S'
_chemical_formula_weight         320.24
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.264(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            6
_cell_length_a                   9.9624(4)
_cell_length_b                   17.8137(8)
_cell_length_c                   12.6175(6)
_cell_measurement_reflns_used    9971
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.59
_cell_measurement_theta_min      2.36
_cell_volume                     2215.94(17)
_computing_cell_refinement       'Bruker SAINT-Plus v7.66A'
_computing_data_collection       'Bruker APEX2 v2009.7-0'
_computing_data_reduction        'Bruker SAINT-Plus v7.66A'
_computing_molecular_graphics    'Bruker XP v5.1'
_computing_publication_material  'Bruker XCIF 2008'
_computing_structure_refinement  'Bruker XL 2008/1'
_computing_structure_solution    'Bruker XS 2008/1'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX II'
_diffrn_measurement_method       '\w scans; 9 settings'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            50720
_diffrn_reflns_theta_full        29.93
_diffrn_reflns_theta_max         29.93
_diffrn_reflns_theta_min         1.63
_exptl_absorpt_coefficient_mu    2.915
_exptl_absorpt_correction_T_max  0.7274
_exptl_absorpt_correction_T_min  0.6375
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'XPREP v2008/2, Bruker-AXS, Madison, WI'
_exptl_crystal_colour            'Pale yellow'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.896
_refine_diff_density_min         -0.565
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.011(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    Riding
_refine_ls_matrix_type           'Full matrix'
_refine_ls_number_parameters     676
_refine_ls_number_reflns         12745
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0257
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     w=1/s^2^(Fo^2^)
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_gt          0.0308
_refine_ls_wR_factor_ref         0.0315
_reflns_number_gt                10731
_reflns_number_total             12745
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1sc00095k.txt
_cod_data_source_block           run02
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Gaussian'
changed to 'gaussian' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_refine_ls_weighting_scheme' value 'Sigma' changed to
'sigma' according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

The following automatic conversions were performed:

'_atom_sites_solution_primary' value 'Direct methods' was changed to
'direct'.

'_atom_sites_solution_secondary' value 'Difference Fourier map' was
changed to 'difmap'.

'_atom_sites_solution_hydrogens' value 'Geometric positions' was
changed to 'geom'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               1515546