Efficient access to materials-oriented aromatic alkynes via the mechanochemical Sonogashira coupling of solid aryl halides with large polycyclic conjugated systems
Gao, Yunpeng; Feng, Chi; Seo, Tamae; Kubota, Koji; Ito, Hajime; Chemical Science 13 (2022) 430–438; doi:10.1039/D1SC05257H

data_1565602
_publ_section_title
;
 Efficient access to materials-oriented aromatic alkynes via the
 mechanochemical Sonogashira coupling of solid aryl halides with large
 polycyclic conjugated systems
;
_journal_issue                   2
_journal_name_full               'Chemical Science'
_journal_page_first              430
_journal_page_last               438
_journal_paper_doi               10.1039/D1SC05257H
_journal_volume                  13
_journal_year                    2022
_chemical_formula_moiety         'C40 H52 O2 S2 Si2'
_chemical_formula_sum            'C40 H52 O2 S2 Si2'
_chemical_formula_weight         685.11
_chemical_melting_point          567.5(15)
_chemical_name_systematic
5,5''''-bis((triisopropylsilyl)ethynyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
_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             2021-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                105.307(3)
_cell_angle_beta                 109.588(4)
_cell_angle_gamma                90.479(3)
_cell_formula_units_Z            4
_cell_length_a                   14.2639(6)
_cell_length_b                   14.5005(4)
_cell_length_c                   20.4969(7)
_cell_measurement_reflns_used    10347
_cell_measurement_temperature    123
_cell_measurement_theta_max      75.9920
_cell_measurement_theta_min      3.1320
_cell_volume                     3830.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.110a (Rigaku OD, 2021)'
_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      123
_diffrn_detector                 'PLATUS 200K area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.781
_diffrn_measured_fraction_theta_max 0.738
_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     67.00  93.00   0.50    0.50    --    5.00  55.00  30.00   52
  2  \w     10.00  47.00   0.50    0.50    --  -42.82  46.00-120.00   74
  3  \w    -82.00 -30.00   0.50    0.50    --  -42.82  46.00-120.00  104
  4  \w   -132.00 -85.00   0.50    0.50    --  -42.82  46.00-120.00   94
  5  \w   -134.00  45.00   0.50    0.50    --  -44.78  46.00 -60.00  358
  6  \w   -178.00 -24.00   0.50    1.54    -- -110.00  55.00-104.10  308
  7  \w    -80.00 -21.00   0.50    1.54    -- -110.00   0.00 -30.00  118
  8  \w   -172.00-135.00   0.50    1.54    -- -110.00  55.00 -31.58   74
  9  \w   -188.00-157.00   0.50    1.54    -- -110.00  54.00-139.17   62
 10  \w   -134.00-107.00   0.50    1.54    -- -110.00   0.00 -30.00   54
 11  \w   -166.00-116.00   0.50    1.54    -- -110.00  55.00 -53.97  100
 12  \w    -72.00 -28.00   0.50    1.54    -- -110.00  55.00 -53.97   88
 13  \w   -122.00 -21.00   0.50    1.54    -- -110.00  55.00 -31.58  202
 14  \w   -199.00 -71.00   0.50    1.54    -- -110.00  49.00-131.53  256
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1033154000
_diffrn_orient_matrix_UB_12      -0.0140010000
_diffrn_orient_matrix_UB_13      0.0065614000
_diffrn_orient_matrix_UB_21      0.0436734000
_diffrn_orient_matrix_UB_22      0.0558632000
_diffrn_orient_matrix_UB_23      0.0806967000
_diffrn_orient_matrix_UB_31      -0.0266785000
_diffrn_orient_matrix_UB_32      0.0946341000
_diffrn_orient_matrix_UB_33      -0.0190889000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.781
_diffrn_reflns_Laue_measured_fraction_max 0.738
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22451
_diffrn_reflns_point_group_measured_fraction_full 0.781
_diffrn_reflns_point_group_measured_fraction_max 0.738
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.522
_diffrn_reflns_theta_min         2.386
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72434
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.110a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_description       plate
_exptl_crystal_F_000             1472
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane/dichloromethane'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.099
_refine_ls_extinction_coef       0.00101(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     858
_refine_ls_number_reflns         11884
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0408
_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^)+(0.0703P)^2^+1.1402P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1090
_refine_ls_wR_factor_ref         0.1148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10433
_reflns_number_total             11884
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05257h2.cif
_cod_data_source_block           20210818-gyp-1-3ac-3_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '566-569' was changed to
'567.5(15)' -- the average value was taken and precision was
estimated.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 1565602--1565603.cif.
;
_cod_database_code               1565602
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H O S Si'
_shelx_estimated_absorpt_t_max   0.921
_shelx_estimated_absorpt_t_min   0.622
_diffrn_oxdiff_digest_frames
;
012c6e8689d061ef3e4638972eb59fbeb0000311525
;
_diffrn_oxdiff_digest_hkl
;
016ff7fe06f594aa8b25eefdd62b8dd7704330
;
_reflns_odcompleteness_completeness 78.21
_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:
 C41(H41), C87(H87), C27(H27), C73(H73), C68(H68), C70(H70), C22(H22),
 C24(H24), C82(H82), C36(H36), C38(H38), C84(H84)
2.b Aromatic/amide H refined with riding coordinates:
 C51(H51), C61(H61), C14(H14), C53(H53), C8(H8), C6(H6), C16(H16), C63(H63)
2.c Idealised Me refined as rotating group:
 C43(H43A,H43B,H43C), C32(H32A,H32B,H32C), C69(H69A,H69B,H69C), C92(H92A,H92B,
 H92C), C75(H75A,H75B,H75C), C74(H74A,H74B,H74C), C72(H72A,H72B,H72C), C42(H42A,
 H42B,H42C), C46(H46A,H46B,H46C), C89(H89A,H89B,H89C), C78(H78A,H78B,H78C),
 C29(H29A,H29B,H29C), C88(H88A,H88B,H88C), C83(H83A,H83B,H83C), C76(H76A,H76B,
 H76C), C86(H86A,H86B,H86C), C26(H26A,H26B,H26C), C71(H71A,H71B,H71C), C40(H40A,
 H40B,H40C), C28(H28A,H28B,H28C), C85(H85A,H85B,H85C), C25(H25A,H25B,H25C),
 C23(H23A,H23B,H23C), C37(H37A,H37B,H37C), C44(H44A,H44B,H44C), C90(H90A,H90B,
 H90C), C30(H30A,H30B,H30C), C39(H39A,H39B,H39C)
;
_shelx_res_checksum              98404
_shelx_hkl_checksum              20619
_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 1.555
_oxdiff_exptl_absorpt_empirical_full_min 0.722