C-H arylation of thiopyran derivatives with aryl halides.
Su, Yangzhe; Wang, Min; Xu, Jianping; Chen, Weinan; Zhou, Gang; Chemical communications (Cambridge, England) 60 (2024) 5193–5196; doi:10.1039/d4cc00719k

data_7132961
_publ_section_title
;
 C-H arylation of thiopyran derivatives with aryl halides.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5193
_journal_page_last               5196
_journal_paper_doi               10.1039/d4cc00719k
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C34 H34 S2'
_chemical_formula_sum            'C34 H34 S2'
_chemical_formula_weight         506.73
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   37.256(6)
_cell_length_b                   37.256(6)
_cell_length_c                   5.1212(11)
_cell_measurement_reflns_used    949
_cell_measurement_temperature    170
_cell_measurement_theta_max      64.240
_cell_measurement_theta_min      2.208
_cell_volume                     6155.9(19)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 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      170
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.1123
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_k_max       46
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            6828
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.527
_diffrn_reflns_theta_min         2.187
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  0.7538
_exptl_absorpt_correction_T_min  0.2956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1496 before and 0.0771 after correction. The Ratio of minimum to maximum transmission is 0.3921. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       needle
_exptl_crystal_F_000             2430
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_platon_squeeze_details
;
TITL fd1_0m_a.res in R-3
CELL   37.2560   37.2560    5.1212     90.00     90.00    120.00
SPGR R-3
C101 0.999 0.998 0.063 !       1.64 eA-3
C102 1.000 1.000 0.500 !       1.23 eA-3
C103 0.667 0.339 0.790 !       1.12 eA-3
C104 1.003 1.003 0.301 !       0.87 eA-3
C105 0.999 0.967 0.957 !       0.78 eA-3
Q106 0.329 0.413 0.488 !       0.78 eA-3
C107 0.972 0.998 0.920 !       0.78 eA-3
C108 0.651 0.340 0.563 !       0.72 eA-3
Q109 0.563 0.929 0.697 !       0.55 eA-3
Q110 0.485 0.486 0.497 !       0.53 eA-3
Q111 0.134 0.710 0.128 !       0.51 eA-3
Q112 0.299 0.655 0.068 !       0.51 eA-3
;
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2840
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.1364
_refine_ls_R_factor_gt           0.0694
_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^)+(0.0466P)^2^+8.1367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1663
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1660
_reflns_number_total             2840
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00719k2.cif
_cod_data_source_block           fd1_0m_sq
_cod_depositor_comments
'Adding full bibliography for 7132961--7132963.cif.'
_cod_original_cell_volume        6156(2)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7132961
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.975
_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 Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C1(H1), C4(H4), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C17(H17A,H17B,H17C)
;
_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'