Enantioselective Organocatalytic Sulfenylation of β-Naphthols.
Wang, Jiao-Jiao; Yang, Hui; Gou, Bo-Bo; Zhou, Ling; Chen, Jie; The Journal of organic chemistry 83 (2018) 4730–4738; doi:10.1021/acs.joc.8b00487

data_4034931
_publ_section_title
;
 Enantioselective Organocatalytic Sulfenylation of \b-Naphthols.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4730
_journal_page_last               4738
_journal_paper_doi               10.1021/acs.joc.8b00487
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration rm
_chemical_formula_moiety         'C24 H17 Br N2 O6 S'
_chemical_formula_sum            'C24 H17 Br N2 O6 S'
_chemical_formula_weight         541.36
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-01-03
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2015.08.17 svn.r3210 for OlexSys, GUI svn.r5083)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.3061(16)
_cell_length_b                   12.000(3)
_cell_length_c                   30.470(8)
_cell_measurement_reflns_used    1802
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.96
_cell_measurement_theta_min      3.16
_cell_volume                     2305.8(10)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0829
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            11744
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.097
_diffrn_reflns_theta_max         25.097
_diffrn_reflns_theta_min         2.160
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5539
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1169 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.7432.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.189
_exptl_crystal_size_mid          0.165
_exptl_crystal_size_min          0.134
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 754 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.035(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0892
_refine_ls_R_factor_gt           0.0459
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0215P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0871
_refine_ls_wR_factor_ref         0.1017
_reflns_Friedel_coverage         0.714
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2525
_reflns_number_total             4113
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00487_si_002.cif
_cod_data_source_block           crystal
_cod_database_code               4034931
_shelx_estimated_absorpt_t_max   0.783
_shelx_estimated_absorpt_t_min   0.713
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C20(H20), C22(H22), C24(H24), C10(H10), C11(H11), C17(H17), C16(H16),
 C15(H15), C14(H14), C3(H3), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              37776
_shelx_hkl_checksum              36655
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'