Copper-catalyzed diastereoselective hydrothioetherification of oxa(aza)benzonorbornadienes.
Lin, Qifu; Yao, Yongqi; Yang, Wen; Tan, Yun; Chen, Shuqi; Chen, Donghan; Yang, Dingqiao; Organic & biomolecular chemistry 18 (2020) 3575–3584; doi:10.1039/d0ob00659a

data_7157473
_publ_section_title
;
 Copper-catalyzed diastereoselective hydrothioetherification of
 oxa(aza)benzonorbornadienes.
;
_journal_issue                   18
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3575
_journal_page_last               3584
_journal_paper_doi               10.1039/d0ob00659a
_journal_volume                  18
_journal_year                    2020
_chemical_formula_moiety         'C18 H18 O3 S'
_chemical_formula_sum            'C18 H18 O3 S'
_chemical_formula_weight         314.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-05
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2019-12-05 deposited with the CCDC.	2020-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.085(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.54660(10)
_cell_length_b                   9.9811(2)
_cell_length_c                   27.5422(5)
_cell_measurement_reflns_used    4003
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.4690
_cell_measurement_theta_min      3.2240
_cell_volume                     1524.50(5)
_computing_cell_refinement       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -88.00 -30.00   0.50    0.99    --    0.00 -19.00 150.00  116
  2  \w    -38.00  25.00   0.50    0.99    --    0.00 -77.00  30.00  126
  3  \w    -21.00   8.00   0.50    0.99    --    0.00 -19.00 150.00   58
  4  \w     72.00 155.00   0.50    3.97    --   95.20  15.00   0.00  166
  5  \w     73.00 145.00   0.50    3.97    --   95.20  61.00-120.00  144
  6  \w     17.00  43.00   0.50    3.97    --   95.20 -45.00  90.00   52
  7  \w     65.00  96.00   0.50    3.97    --   95.20 -45.00-150.00   62
  8  \w     50.00 115.00   0.50    3.97    --   95.20 -45.00  90.00  130
  9  \w      7.00 117.00   0.50    3.97    --   95.20 -61.00  90.00  220
 10  \w     80.00 106.00   0.50    3.97    --   95.20  45.00-120.00   52
 11  \w     46.00 112.00   0.50    3.97    --   95.20 -30.00-150.00  132
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1129952000
_diffrn_orient_matrix_UB_12      0.1222776000
_diffrn_orient_matrix_UB_13      0.0249950000
_diffrn_orient_matrix_UB_21      0.0889830000
_diffrn_orient_matrix_UB_22      -0.0528064000
_diffrn_orient_matrix_UB_23      0.0497784000
_diffrn_orient_matrix_UB_31      0.2375248000
_diffrn_orient_matrix_UB_32      0.0779542000
_diffrn_orient_matrix_UB_33      -0.0055388000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            6733
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.479
_diffrn_reflns_theta_max         67.479
_diffrn_reflns_theta_min         3.210
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.270
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         2749
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0664P)^2^+0.4318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1143
_refine_ls_wR_factor_ref         0.1178
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2469
_reflns_number_total             2749
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ob00659a2.cif
_cod_data_source_block           wang_20191205
_cod_depositor_comments          'Adding full bibliography for 7157473.cif.'
_cod_database_code               7157473
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.756
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.a Ternary CH refined with riding coordinates:
 C007(H007), C00A(H00A), C00G(H00G)
2.b Secondary CH2 refined with riding coordinates:
 C00F(H00D,H00F)
2.c Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00E(H00E), C00H(H00H), C00J(H00L), C00K(H00M),
 C00L(H00N)
2.d Idealised Me refined as rotating group:
 C00I(H00I,H00J,H00K), C00M(H00O,H00P,H00Q)
;
_shelx_res_checksum              86135
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.617