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_7132962
_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         'C30 H22 S'
_chemical_formula_sum            'C30 H22 S'
_chemical_formula_weight         414.53
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-08-01
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2023-11-27 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.323(2)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.9168(3)
_cell_length_b                   5.12150(10)
_cell_length_c                   80.8465(18)
_cell_measurement_reflns_used    9188
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      69.4570
_cell_measurement_theta_min      3.6110
_cell_volume                     6171.3(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.92a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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    -85.00  20.26   0.38    1.50    --    0.00 -57.00 -30.00  277
  2  \w     54.00 144.82   0.38    6.00    --   87.20  30.00 -60.00  239
  3  \w     73.00 124.30   0.38    6.00    --   87.20  45.00   0.00  135
  4  \w    129.00 176.50   0.38    6.00    --   87.20  45.00   0.00  125
  5  \w     24.00 109.12   0.38    6.00    --   87.20 -82.00  90.00  224
  6  \w      6.00  32.22   0.38    6.00    --   87.20 -77.00-180.00   69
  7  \w     59.00 111.82   0.38    6.00    --   87.20 -77.00-180.00  139
  8  \w      1.00  90.30   0.38    6.00    --   87.20 -61.00  90.00  235
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0760338000
_diffrn_orient_matrix_UB_12      0.0514969000
_diffrn_orient_matrix_UB_13      -0.0130590000
_diffrn_orient_matrix_UB_21      -0.0528774000
_diffrn_orient_matrix_UB_22      0.1485721000
_diffrn_orient_matrix_UB_23      0.0129965000
_diffrn_orient_matrix_UB_31      0.0459610000
_diffrn_orient_matrix_UB_32      0.2563767000
_diffrn_orient_matrix_UB_33      -0.0049187000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_unetI/netI     0.0828
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       94
_diffrn_reflns_limit_l_min       -68
_diffrn_reflns_number            22991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        63.994
_diffrn_reflns_theta_max         63.994
_diffrn_reflns_theta_min         3.202
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_exptl_absorpt_coefficient_mu    1.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.92a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       needle
_exptl_crystal_F_000             2616
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.550
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.136
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     841
_refine_ls_number_reflns         10092
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.136
_refine_ls_R_factor_all          0.1025
_refine_ls_R_factor_gt           0.0778
_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^)+(0.0310P)^2^+17.2376P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1630
_refine_ls_wR_factor_ref         0.1717
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7600
_reflns_number_total             10092
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00719k2.cif
_cod_data_source_block           230722ck1
_cod_depositor_comments
'Adding full bibliography for 7132961--7132963.cif.'
_cod_database_code               7132962
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N S'
_chemical_oxdiff_usercomment     'HYL ORGANIC'
_reflns_odcompleteness_completeness 99.13
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     64.99
_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:
 C01B(H01A,H01B), C01E(H01C,H01E), C01K(H01G,H01H), C023(H02N,H02O), C026(H02A,
 H02B), C02C(H02E,H02F), C02E(H02Q,H02R), C02G(H02G,H02H), C02J(H02T,H02U)
2.b Aromatic/amide H refined with riding coordinates:
 C007(H007), C00M(H00M), C00R(H00R), C00V(H00V), C00Y(H00Y), C010(H010),
 C011(H011), C017(H017), C019(H019), C01C(H01O), C01D(H01D), C01F(H01F),
 C01I(H01I), C01J(H01J), C01N(H01N), C01O(H01R), C01P(H01P), C01Q(H01Q),
 C01S(H01S), C01U(H01U), C01V(H01V), C01W(H01W), C01X(H01X), C01Y(H01Y),
 C01Z(H01Z), C020(H020), C021(H021), C022(H022), C024(H024), C025(H025),
 C027(H027), C028(H028), C029(H029), C02A(H02C), C02B(H02D), C02D(H02P),
 C02F(H02S), C02H(H02I), C02I(H02J)
2.c Idealised Me refined as rotating group:
 C01R(H01K,H01L,H01M), C02K(H02K,H02L,H02M), C02L(H02V,H02W,H02X)
;
_shelx_res_checksum              58515
_shelx_hkl_checksum              75679
_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 1.274
_oxdiff_exptl_absorpt_empirical_full_min 0.651