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_1565603
_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         'C42 H52 S5 Si2'
_chemical_formula_sum            'C42 H52 S5 Si2'
_chemical_formula_weight         773.31
_chemical_melting_point          415.0(10)
_chemical_name_systematic
5,5''''-bis((triisopropylsilyl)ethynyl)-2,2':5',2'':5'',2''':5''',2''''-quinquethiophene
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-08-28
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2021-08-30 deposited with the CCDC.	2021-12-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.9160(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   39.5034(4)
_cell_length_b                   9.23520(10)
_cell_length_c                   23.1512(3)
_cell_measurement_reflns_used    12050
_cell_measurement_temperature    123
_cell_measurement_theta_max      75.9840
_cell_measurement_theta_min      3.8520
_cell_volume                     8384.61(17)
_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 0.992
_diffrn_measured_fraction_theta_max 0.955
_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   -132.00 -94.00   0.50    0.50    --  -42.99   0.00-180.00   76
  2  \w    -68.00 -35.00   0.50    0.50    --  -42.99  46.00 120.00   66
  3  \w   -131.00 -36.00   0.50    0.50    --  -42.99  55.00-120.00  190
  4  \w    -44.00  -1.00   0.50    0.50    --  -42.99   0.00-180.00   86
  5  \w     13.00  40.00   0.50    0.50    --  -42.99  46.00 120.00   54
  6  \w   -131.00 -71.00   0.50    0.50    --  -42.99  46.00 120.00  120
  7  \w   -199.00 -21.00   0.50    0.50    -- -110.00  54.00-104.32  356
  8  \w   -189.00 -90.00   0.50    0.50    -- -110.00  37.00-120.00  198
  9  \w   -166.00 -41.00   0.50    0.50    -- -110.00   9.00  30.00  250
 10  \w    -73.00 -28.00   0.50    0.50    -- -110.00  37.00 -90.00   90
 11  \w   -136.00-111.00   0.50    0.50    -- -110.00  37.00 -90.00   50
 12  \w    -54.00 -29.00   0.50    0.50    -- -110.00  52.00 -54.97   50
;
_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      0.0020756000
_diffrn_orient_matrix_UB_12      -0.1581773000
_diffrn_orient_matrix_UB_13      -0.0205274000
_diffrn_orient_matrix_UB_21      0.0375257000
_diffrn_orient_matrix_UB_22      0.0233756000
_diffrn_orient_matrix_UB_23      -0.0097474000
_diffrn_orient_matrix_UB_31      0.0114827000
_diffrn_orient_matrix_UB_32      -0.0476189000
_diffrn_orient_matrix_UB_33      0.0630236000
_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  0.0337
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_h_min       -49
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19756
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.553
_diffrn_reflns_theta_min         3.847
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    3.301
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60100
_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            orange
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       plate
_exptl_crystal_F_000             3296
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: methanol/chloroform'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.337
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       0.000039(19)
_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   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     455
_refine_ls_number_reflns         8430
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0343
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+4.9506P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7672
_reflns_number_total             8430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05257h2.cif
_cod_data_source_block           20210721-gyp-olith_auto
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '414-416' was changed to
'415.0(10)' -- 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_original_cell_volume        8384.60(17)
_cod_database_code               1565603
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C H Si S'
_shelx_estimated_absorpt_t_max   0.879
_shelx_estimated_absorpt_t_min   0.438
_diffrn_oxdiff_digest_frames
;
01b80102c8c2a61cccf3a044fa235c967800032dc52
;
_diffrn_oxdiff_digest_hkl
;
01cfce2a46d69dd1843f06b132d8e44c557bb2
;
_reflns_odcompleteness_completeness 99.26
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H49A,H49B,H49C} of C49
 At 1.5 times of:
  {H48A,H48B,H48C} of C48, {H42A,H42B,H42C} of C42, {H47A,H47B,H47C} of C47,
  {H31A,H31B,H31C} of C31, {H25A,H25B,H25C} of C25, {H45A,H45B,H45C} of C45,
  {H44A,H44B,H44C} of C44, {H28A,H28B,H28C} of C28, {H27A,H27B,H27C} of C27,
  {H32A,H32B,H32C} of C32, {H30A,H30B,H30C} of C30
2.a Ternary CH refined with riding coordinates:
 C46(H46), C41(H41), C29(H29), C24(H24), C43(H43), C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C4(H4), C18(H18), C35(H35), C3(H3), C9(H9), C8(H8), C13(H13),
 C36(H36), C19(H19)
2.c Idealised Me refined as rotating group:
 C48(H48A,H48B,H48C), C42(H42A,H42B,H42C), C47(H47A,H47B,H47C), C31(H31A,H31B,
 H31C), C49(H49A,H49B,H49C), C25(H25A,H25B,H25C), C45(H45A,H45B,H45C), C44(H44A,
 H44B,H44C), C28(H28A,H28B,H28C), C32(H32A,H32B,H32C), C27(H27A,H27B,H27C),
 C30(H30A,H30B,H30C)
;
_shelx_res_checksum              40289
_shelx_hkl_checksum              80785
_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 2.002
_oxdiff_exptl_absorpt_empirical_full_min 0.621