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_1556026
_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_formula_moiety         'C46 H34 N4 O S Zn, C H2 Cl2'
_chemical_formula_sum            'C47 H36 Cl2 N4 O S Zn'
_chemical_formula_weight         841.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2016-09-01
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_cell_angle_alpha                98.8680(10)
_cell_angle_beta                 96.1600(10)
_cell_angle_gamma                102.8400(10)
_cell_formula_units_Z            2
_cell_length_a                   11.0032(9)
_cell_length_b                   12.6313(10)
_cell_length_c                   14.7240(12)
_cell_measurement_reflns_used    9918
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.33
_cell_measurement_theta_min      2.21
_cell_volume                     1950.0(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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.932
_diffrn_measured_fraction_theta_max 0.997
_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  0.0435
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_Laue_measured_fraction_full 0.932
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29070
_diffrn_reflns_point_group_measured_fraction_full 0.932
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_min         1.682
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.864
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0570 before and 0.0527 after correction. The Ratio of minimum to maximum transmission is 0.9334. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_description       chunk
_exptl_crystal_F_000             868
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.243
_exptl_crystal_size_mid          0.223
_exptl_crystal_size_min          0.195
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     519
_refine_ls_number_reflns         7160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0438
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0574P)^2^+1.2822P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1078
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5933
_reflns_number_total             7160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b00495_si_003.cif
_cod_data_source_block           bb916a
_cod_database_code               1556026
_shelxl_version_number           2014/6
_shelx_estimated_absorpt_t_max   0.850
_shelx_estimated_absorpt_t_min   0.818
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C46) = Uanis(C46B)
Uanis(C45) = Uanis(C45B)
Uanis(S1) = Uanis(S1B)
3. Others
 Sof(S1B)=Sof(C45B)=Sof(H45D)=Sof(H45E)=Sof(H45F)=Sof(C46B)=Sof(H46D)=
 Sof(H46E)=Sof(H46F)=1-FVAR(1)
 Sof(S1)=Sof(C45)=Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(C46)=Sof(H46A)=Sof(H46B)=
 Sof(H46C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C1S(H1SA,H1SB)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C12(H12), C13(H13), C17(H17), C18(H18),
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C28(H28), C29(H29), C30(H30),
  C31(H31), C32(H32), C34(H34), C35(H35), C36(H36), C37(H37), C38(H38),
 C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
4.c Idealised Me refined as rotating group:
 C45(H45A,H45B,H45C), C45B(H45D,H45E,H45F), C46(H46A,H46B,H46C), C46B(H46D,
 H46E,H46F)
;
_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 'Large red crystal'
_olex2_submission_special_instructions 'No special instructions were received'