Synthesis of dithienofurans via cascade copper catalysed dual C–S coupling and ring closure reactions under mild conditions
Zhou, Lu; Chen, Zhaopeng; Li, Jiahui; Li, Baolin; RSC Advances 11 (2021) 34071–34078; doi:10.1039/D1RA06881D

data_7243786
_publ_section_title
;
 Synthesis of dithienofurans via cascade copper catalysed dual C--S
 coupling and ring closure reactions under mild conditions
;
_journal_issue                   54
_journal_name_full               'RSC Advances'
_journal_page_first              34071
_journal_page_last               34078
_journal_paper_doi               10.1039/D1RA06881D
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C26 H24 O S2'
_chemical_formula_sum            'C26 H24 O S2'
_chemical_formula_weight         416.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-04-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-07-02 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.6526(2)
_cell_length_b                   10.0371(3)
_cell_length_c                   36.8324(15)
_cell_measurement_reflns_used    2048
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.5810
_cell_measurement_theta_min      4.5540
_cell_volume                     2089.71(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.969
_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     25.00  51.00   1.00    1.00    --   40.73  38.00 -90.00   26
  2  \w     90.00 115.00   1.00    1.00    --   40.73  38.00 -90.00   25
  3  \w    127.00 154.00   1.00    2.00    --  107.58  45.00 -90.00   27
  4  \w    120.00 175.00   1.00    2.00    --  107.58 125.00-180.00   55
  5  \w     56.00 162.00   1.00    2.00    --  107.58  15.00  30.00  106
  6  \w     37.00  68.00   1.00    1.00    --   40.73 -99.00  90.00   31
  7  \w     28.00  74.00   1.00    2.00    --  107.58 -94.00 120.00   46
  8  \w   -113.00 -16.00   1.00    1.00    --  -40.73 -38.00  60.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0376064000
_diffrn_orient_matrix_UB_12      0.1005626000
_diffrn_orient_matrix_UB_13      0.0310775000
_diffrn_orient_matrix_UB_21      0.0497705000
_diffrn_orient_matrix_UB_22      -0.1157256000
_diffrn_orient_matrix_UB_23      0.0263892000
_diffrn_orient_matrix_UB_31      0.2652526000
_diffrn_orient_matrix_UB_32      0.0073966000
_diffrn_orient_matrix_UB_33      -0.0093691000
_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  0.0326
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            5045
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.688
_diffrn_reflns_theta_min         2.399
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.411
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       needle
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 821 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.032(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         3352
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0511P)^2^+2.1820P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1297
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.400
_reflns_Friedel_fraction_full    0.607
_reflns_Friedel_fraction_max     0.552
_reflns_number_gt                3079
_reflns_number_total             3352
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ra06881d2.cif
_cod_data_source_block           z04
_cod_database_code               7243786
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C13(H13), C16(H16), C17(H17),
 C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C), C26(H26A,H26B,
 H26C)
;
_shelx_res_checksum              94958
_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 1.295
_oxdiff_exptl_absorpt_empirical_full_min 0.549