Absolute Stereochemical Determination of Asymmetric Sulfoxides via Central to Axial Induction of Chirality.
Gholami, Hadi; Zhang, Jun; Anyika, Mercy; Borhan, Babak; Organic letters 19 (2017) 1722–1725; doi:10.1021/acs.orglett.7b00495

data_1556027
_publ_section_title
;
 Absolute Stereochemical Determination of Asymmetric Sulfoxides via
 Central to Axial Induction of Chirality.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1722
_journal_page_last               1725
_journal_paper_doi               10.1021/acs.orglett.7b00495
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C51 H37 N5 O S Zn'
_chemical_formula_sum            'C51 H37 N5 O S Zn'
_chemical_formula_weight         833.28
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-11-11
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.11.07 svn.r3352 for OlexSys, GUI svn.r5261)
;
_cell_angle_alpha                83.4570(10)
_cell_angle_beta                 84.1520(10)
_cell_angle_gamma                77.5190(10)
_cell_formula_units_Z            2
_cell_length_a                   10.6689(10)
_cell_length_b                   10.8762(10)
_cell_length_c                   18.2817(17)
_cell_measurement_reflns_used    9141
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.32
_cell_volume                     2051.2(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            33389
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_min         1.926
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.695
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.7055
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0579 before and 0.0525 after correction. The Ratio of minimum to maximum transmission is 0.9467. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_description       chunk
_exptl_crystal_F_000             864
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.273
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.661
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.061
_refine_ls_abs_structure_details
;
 Flack x determined using 5521 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1065
_refine_ls_number_reflns         14993
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.994
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0636P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1007
_refine_ls_wR_factor_ref         0.1067
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                12556
_reflns_number_total             14993
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00495_si_002.cif
_cod_data_source_block           bb1116a
_cod_database_code               1556027
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.833
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2A(H2A), C3A(H3A), C5A(H5A), C6A(H6A), C9A(H9A), C10A(H10A), C14A(H14A),
 C15A(H15A), C19A(H19A), C20A(H20A), C24A(H24A), C25A(H25A), C29A(H29A),
 C30A(H30A), C31A(H31A), C32A(H32A), C33A(H33A), C35A(H35A), C36A(H36A),
 C37A(H37A), C38A(H38A), C39A(H39A), C41A(H41A), C42A(H42A), C43A(H43A),
 C44A(H44A), C45A(H45A), C47A(H47A), C48A(H48A), C49A(H49A), C50A(H50A),
 C51A(H51A), C2B(H2B), C3B(H3B), C5B(H5B), C6B(H6B), C9B(H9B), C10B(H10B),
 C14B(H14B), C15B(H15B), C19B(H19B), C20B(H20B), C24B(H24B), C25B(H25B),
 C29B(H29B), C30B(H30B), C31B(H31B), C32B(H32B), C33B(H33B), C35B(H35B),
 C36B(H36B), C37B(H37B), C38B(H38B), C39B(H39B), C41B(H41B), C42B(H42B),
 C43B(H43B), C44B(H44B), C45B(H45B), C47B(H47B), C48B(H48B), C49B(H49B),
 C50B(H50B), C51B(H51B)
2.b X=CH2 refined with riding coordinates:
 N1A(H1AA,H1AB), N1B(H1BA,H1BB)
2.c Idealised Me refined as rotating group:
 C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,H7BC)
;
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id HG-05-064-ZnTPP-Sulfinamide
_olex2_submission_special_instructions 'No special instructions were received'