A carbon-functionality-appended diborylacetylene available for a component of organic synthesis and OLEDs
Tsukada, Tetsuyoshi; Shoji, Yoshiaki; Takenouchi, Kumiko; Taka, Hideo; Fukushima, Takanori; Chemical Communications  (2022) –; doi:10.1039/D2CC01159J

data_7129897
_publ_section_title
;
 A carbon-functionality-appended diborylacetylene available for a
 component of organic synthesis and OLEDs
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01159J
_journal_year                    2022
_chemical_formula_moiety         'C26 H16 B2 O2'
_chemical_formula_sum            'C26 H16 B2 O2'
_chemical_formula_weight         382.01
_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     iterative
_audit_creation_date             2022-02-15
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-02-25 deposited with the CCDC.	2022-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                70.147(5)
_cell_angle_beta                 73.252(4)
_cell_angle_gamma                86.127(4)
_cell_formula_units_Z            2
_cell_length_a                   9.1910(4)
_cell_length_b                   9.2332(5)
_cell_length_c                   12.5455(7)
_cell_measurement_reflns_used    4054
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      70.6210
_cell_measurement_theta_min      3.8940
_cell_volume                     958.35(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_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    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.977
_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    -30.00  16.00   0.50    0.05    --   55.45 -15.00 -90.00   92
  2  \w    -34.00  36.00   0.50    0.05    --   55.45 -30.00   0.00  140
  3  \w    -20.00   6.00   0.50    0.05    --   55.45 -30.00  60.00   52
  4  \w     32.00  57.00   0.50    0.05    --    0.00 -99.00 120.00   50
  5  \w     45.00 110.00   0.50    0.05    --   55.45-125.00  90.00  130
  6  \w     71.00 106.00   0.50    0.05    --  110.90-111.00  30.00   70
  7  \w     76.00 103.00   0.50    0.05    --  110.90 -77.00  60.00   54
  8  \w     75.00 102.00   0.50    0.05    --  110.90 -91.00 120.00   54
  9  \w     50.00 106.00   0.50    0.05    --  110.90 -91.00  30.00  112
 10  \w     50.00  76.00   0.50    0.05    --  110.90 -63.00  90.00   52
 11  \w     32.00  58.00   0.50    0.05    --  110.90 -50.00 120.00   52
 12  \w     27.00  70.00   0.50    0.05    --  110.90 -63.00 150.00   86
 13  \w     28.00  58.00   0.50    0.05    --  110.90 -50.00 150.00   60
 14  \w     17.00  42.00   0.50    0.05    --  110.90 -91.00 120.00   50
 15  \w     16.00  60.00   0.50    0.05    --  110.90 -77.00  60.00   88
 16  \w     27.00  55.00   0.50    0.05    --  110.90 -50.00  30.00   56
 17  \w     42.00  68.00   0.50    0.05    --  110.90 -63.00 -30.00   52
 18  \w     46.00  72.00   0.50    0.05    --  110.90 -63.00 -60.00   52
 19  \w     60.00 106.00   0.50    0.05    --  110.90 -97.00-121.00   92
 20  \w     73.00 102.00   0.50    0.05    --  110.90 -77.00-120.00   58
 21  \w     52.00  77.00   0.50    0.05    --   55.45-125.00-150.00   50
 22  \w     28.00  68.00   0.50    0.05    --   55.45 -97.00-121.00   80
 23  \w     19.00  45.00   0.50    0.05    --   55.45-125.00-150.00   52
 24  \w    -10.00  19.00   0.50    0.05    --    0.00 -97.00-121.00   58
 25  \w    -20.00   5.00   0.50    0.05    --  -28.75 -97.00-121.00   50
 26  \w    -29.00  46.00   0.50    0.05    --   55.45 -45.00-180.00  150
 27  \w     17.00  50.00   0.50    0.05    --  110.90 -77.00-120.00   66
 28  \w     27.00  65.00   0.50    0.05    --  110.90 -63.00-120.00   76
 29  \w     32.00  57.00   0.50    0.05    --  110.90 -50.00-120.00   50
 30  \w     30.00  56.00   0.50    0.05    --  110.90 -50.00 -60.00   52
 31  \w     27.00  54.00   0.50    0.05    --  110.90 -50.00 -90.00   54
 32  \w     35.00 172.00   0.50    0.05    --  110.90  12.00-120.00  274
 33  \w    132.00 168.00   0.50    0.05    --  110.90  37.00-150.00   72
 34  \w    100.00 128.00   0.50    0.05    --   55.45  97.00 -13.00   56
 35  \w     87.00 135.00   0.50    0.05    --   55.45 125.00  30.00   96
 36  \w    105.00 153.00   0.50    0.05    --  110.90  97.00 -13.00   96
 37  \w    126.00 168.00   0.50    0.05    --  110.90  50.00  60.00   84
 38  \w     91.00 136.00   0.50    0.05    --   55.45 125.00 -90.00   90
 39  \w     90.00 136.00   0.50    0.05    --   55.45 125.00-120.00   92
 40  \w     70.00  95.00   0.50    0.05    --  110.90  37.00-150.00   50
 41  \w     14.00  40.00   0.50    0.05    --  110.90 -91.00  30.00   52
 42  \w     41.00 110.00   0.50    0.05    --   55.45-125.00 -30.00  138
 43  \w     49.00 106.00   0.50    0.05    --  110.90-111.00-120.00  114
 44  \w    -13.00  16.00   0.50    0.05    --    0.00 -99.00 120.00   58
 45  \w    -41.00  19.00   0.50    0.05    --   55.45 -15.00 -60.00  120
 46  \w     71.00 132.00   0.50    0.05    --   55.45  61.00  60.00  122
 47  \w     83.00 137.00   0.50    0.05    --   55.45 125.00  90.00  108
 48  \w     69.00  95.00   0.50    0.05    --  110.90  50.00  60.00   52
 49  \w     73.00 168.00   0.50    0.05    --  110.90  63.00 120.00  190
 50  \w     63.00 160.00   0.50    0.05    --  110.90  77.00  90.00  194
 51  \w     18.00  52.00   0.50    0.05    --   55.45  61.00  60.00   68
 52  \w    -25.00   0.00   0.50    0.05    --    0.00  97.00 -13.00   50
 53  \w    -17.00   8.00   0.50    0.05    --  -28.75  97.00 -13.00   50
 54  \w   -110.00 -80.00   0.50    0.05    --  -28.75 -91.00 -30.00   60
 55  \w   -126.00 -94.00   0.50    0.05    --  -28.75 -91.00 -60.00   64
 56  \w   -108.00 -82.00   0.50    0.05    --  -28.75 -91.00  90.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-DW'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0113468000
_diffrn_orient_matrix_UB_12      -0.1773929000
_diffrn_orient_matrix_UB_13      0.0482719000
_diffrn_orient_matrix_UB_21      -0.0157505000
_diffrn_orient_matrix_UB_22      -0.0017198000
_diffrn_orient_matrix_UB_23      -0.1185431000
_diffrn_orient_matrix_UB_31      0.1740622000
_diffrn_orient_matrix_UB_32      -0.0057078000
_diffrn_orient_matrix_UB_33      -0.0462857000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7614
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.783
_diffrn_reflns_theta_min         3.905
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              PhotonJet-DW
_exptl_absorpt_coefficient_mu    0.634
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             396
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0449P)^2^+0.2864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0948
_refine_ls_wR_factor_ref         0.0970
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3253
_reflns_number_total             3610
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01159j2.cif
_cod_data_source_block           tkd-01-09-4
_cod_database_code               7129897
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H B O'
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.884
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25)
;
_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 1.195
_oxdiff_exptl_absorpt_empirical_full_min 0.879