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_4514851
_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         'C23 H19 N S2'
_chemical_formula_sum            'C23 H19 N S2'
_chemical_formula_weight         373.51
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_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                 95.273(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.584(2)
_cell_length_b                   4.3460(12)
_cell_length_c                   40.473(8)
_cell_measurement_reflns_used    2031
_cell_measurement_temperature    100
_cell_measurement_theta_max      67.606
_cell_measurement_theta_min      4.244
_cell_volume                     1853.8(7)
_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      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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     1.54178
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.1202
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            7925
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.386
_diffrn_reflns_theta_min         2.192
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker MicroStar FR-592'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.631
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.4511
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1321 before and 0.0706 after correction. The Ratio of minimum to maximum transmission is 0.5990. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       plate
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.682
_refine_diff_density_min         -0.682
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3200
_refine_ls_number_restraints     258
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1292
_refine_ls_R_factor_gt           0.0996
_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^)+(0.0757P)^2^+9.1273P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2305
_refine_ls_wR_factor_ref         0.2467
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2325
_reflns_number_total             3200
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b01471_si_007.cif
_cod_data_source_block           engle78_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_database_code               4514851
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.621
_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(C18) = Uanis(C25)
Uanis(C24) = Uanis(C29)
Uanis(C21) = Uanis(C22)
Uanis(C27) = Uanis(C20)
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(H00H)=Sof(C17)=Sof(H0AA)=Sof(C24)=Sof(C19)=Sof(H00T)=Sof(C20)=Sof(H5AA)=
 Sof(C27)=Sof(H4AA)=Sof(C28)=Sof(H3AA)=Sof(C29)=Sof(H2AA)=1-FVAR(1)
 Sof(H16)=Sof(C00G)=Sof(H00G)=Sof(C18)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26)=
 Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C14(H14), C16(H16), C16(H00H), C13(H13), C00G(H00G), C5(H5),
 C25(H25), C26(H26), C21(H21), C22(H22), C23(H23), C2(H2), C4(H4), C3(H3),
 C17(H0AA), C19(H00T), C20(H5AA), C27(H4AA), C28(H3AA), C29(H2AA)
5.b Fitted hexagon refined as free rotating group:
 C18(C25,C26,C21,C22,C23), C24(C19,C20,C27,C28,C29)
5.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_shelx_res_checksum              68408
_shelx_hkl_checksum              66009
_olex2_submission_special_instructions 'No special instructions were received'