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_7132963
_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         'C27 H24 S'
_chemical_formula_sum            'C27 H24 S'
_chemical_formula_weight         380.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-11-20
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                91.326(2)
_cell_angle_beta                 92.661(3)
_cell_angle_gamma                113.371(3)
_cell_formula_units_Z            4
_cell_length_a                   12.0192(7)
_cell_length_b                   13.1986(7)
_cell_length_c                   13.5978(7)
_cell_measurement_reflns_used    3774
_cell_measurement_temperature    100
_cell_measurement_theta_max      63.67
_cell_measurement_theta_min      3.65
_cell_volume                     1975.96(19)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0699
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14707
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        63.907
_diffrn_reflns_theta_max         63.907
_diffrn_reflns_theta_min         3.257
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.501
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.3919
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1512 before and 0.0972 after correction.
The Ratio of minimum to maximum transmission is 0.5209.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.921
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.128
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         6348
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.1065
_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^)+(0.1324P)^2^+8.1061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2886
_refine_ls_wR_factor_ref         0.2967
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5305
_reflns_number_total             6348
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00719k2.cif
_cod_data_source_block           1120syz1_0m
_cod_depositor_comments
'Adding full bibliography for 7132961--7132963.cif.'
_cod_database_code               7132963
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.806
_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:
 C51(H51A,H51B), C25(H25A,H25B), C50(H50A,H50B), C24(H24A,H24B), C26(H26A,
 H26B), C52(H52A,H52B)
2.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C7(H7), C43(H43), C37(H37), C35(H35), C6(H6), C29(H29), C41(H41),
 C13(H13), C40(H40), C16(H16), C10(H10), C3(H3), C9(H9), C14(H14), C46(H46),
 C2(H2), C31(H31), C33(H33), C44(H44), C45(H45), C19(H19), C18(H18), C17(H17)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C5(H5A,H5B,H5C), C27(H27A,H27B,H27C), C53(H53A,H53B,H53C)
;
_olex2_submission_special_instructions 'No special instructions were received'