Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether Directing Group for Pd(II) Catalysis
Romine, Andrew M.; Yang, Kin S.; Karunananda, Malkanthi K.; Chen, Jason S.; Engle, Keary M.; ACS Catalysis 9 (2019) 7626–; doi:10.1021/acscatal.9b01471

data_4514849
_publ_section_title
;
 Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether
 Directing Group for Pd(II) Catalysis
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              7626
_journal_paper_doi               10.1021/acscatal.9b01471
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C24 H23 N O4 S2'
_chemical_formula_sum            'C24 H23 N O4 S2'
_chemical_formula_weight         453.55
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-02-08
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 105.81
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.796
_cell_length_b                   15.246
_cell_length_c                   9.849
_cell_measurement_reflns_used    3800
_cell_measurement_temperature    200
_cell_measurement_theta_max      68.087
_cell_measurement_theta_min      4.111
_cell_volume                     2282.166
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX3 v2016.9-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            13943
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.155
_diffrn_reflns_theta_min         4.107
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker MicroStar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.367
_exptl_absorpt_correction_T_max  0.7530
_exptl_absorpt_correction_T_min  0.6063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0725 before and 0.0495 after correction. The Ratio of minimum to maximum transmission is 0.8052. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4121
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0631
_refine_ls_R_factor_gt           0.0471
_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^)+(0.0666P)^2^+1.2082P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1300
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3221
_reflns_number_total             4121
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01471_si_002.cif
_cod_data_source_block           engle75_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/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 4973 2017-02-22 13:04:09Z antanas 
;
_cod_original_cell_volume        2282.1
_cod_database_code               4514849
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.871
_shelx_estimated_absorpt_t_min   0.578
_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. Restrained distances
 O4-C22
 1.5 with sigma of 0.001
 C24'-C23' = C23-C22
 1.54 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C21, O4, C22, C23, O4', C23', C24'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(O4')=Sof(C23')=Sof(H23D)=Sof(H23E)=Sof(C24')=Sof(H24A)=Sof(H24B)=
 Sof(H24C)=1-FVAR(1)
 Sof(O4)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C18(H18A,H18B), C22(H22A,H22B), C23'(H23D,H23E)
5.b Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C20(H20)
5.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C23(H23A,H23B,H23C), C24'(H24A,H24B,H24C)
;
_shelx_res_checksum              80312
_shelx_hkl_checksum              28246
_olex2_submission_special_instructions 'No special instructions were received'