One-step selective synthesis of doubly and triply fused chiral boroloborole derivatives.
Bohlen, Josina L.; Wieprecht, Nele; Arrowsmith, Merle; Häfner, Alena; Neder, Marco; Braunschweig, Holger; Chemical communications (Cambridge, England) 60 (2024) 14782–14785; doi:10.1039/d4cc04433a

data_7133974
_publ_section_title
;
 One-step selective synthesis of doubly and triply fused chiral
 boroloborole derivatives.
;
_journal_issue                   99
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              14782
_journal_page_last               14785
_journal_paper_doi               10.1039/d4cc04433a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C26 H18 B2 Cl2'
_chemical_formula_sum            'C26 H18 B2 Cl2'
_chemical_formula_weight         422.92
_chemical_name_systematic        3Bz-Ph
_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
_atom_sites_solution_secondary   difmap
_audit_creation_date             2024-06-14
_audit_creation_method           'CIF-fill 1.5c (K.Radacki, 2005-23)'
_audit_update_record
;
2024-08-23 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                95.172(2)
_cell_angle_beta                 93.665(2)
_cell_angle_gamma                109.945(3)
_cell_formula_units_Z            4
_cell_length_a                   8.5722(3)
_cell_length_b                   12.2762(4)
_cell_length_c                   21.3971(5)
_cell_measurement_reflns_used    11075
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0010
_cell_measurement_theta_min      4.1860
_cell_volume                     2097.22(12)
_computing_cell_refinement       'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_data_collection
;
 CrysAlisPro system (CCD 43.90a 64-bit (release 15-09-2023))
;
_computing_data_reduction        'CrysAlisPro 1.171.43.111a (Rigaku OD, 2024)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)''
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 HPA
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HyPix Arc150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -92.00 -32.00   0.50    0.20    --  -76.37 112.00 150.00  120
  2  \w    -65.00 -31.00   0.50    0.20    --  -76.37 112.00  90.00   68
  3  \w    -95.00 -32.00   0.50    0.20    --  -78.00 114.00 -84.79  126
  4  \w    -64.00 -35.00   0.50    0.20    --  -76.37 112.00-120.00   58
  5  \w    -66.00 -22.00   0.50    0.20    --  -60.36 126.00 -60.00   88
  6  \w     46.00 108.00   0.50    0.20    --   58.45  15.00 -90.00  124
  7  \w     61.00 110.00   0.50    0.20    --   84.34  15.00-180.00   98
  8  \w     46.00  78.00   0.50    0.20    --   58.45  15.00-180.00   64
  9  \w     83.00 108.00   0.50    0.20    --   58.45  15.00-180.00   50
 10  \w     50.00 133.00   0.50    0.20    --   84.34  15.00-120.00  166
 11  \w     48.00 122.00   0.50    0.20    --   84.34  15.00 -30.00  148
 12  \w     44.00 125.00   0.50    0.20    --   76.32  15.00  30.00  162
 13  \w     51.00  76.00   0.50    0.20    --   84.34  15.00  90.00   50
 14  \w     96.00 130.00   0.50    0.20    --   84.34  15.00  90.00   68
 15  \w     40.00 117.00   0.50    0.20    --   76.32  15.00 120.00  154
 16  \w     66.00  91.00   0.50    0.20    --   84.34 -95.00  30.00   50
 17  \w     41.00  75.00   0.50    0.20    --   76.32-112.00 -90.00   68
 18  \w     28.00  56.00   0.50    0.20    --   58.45-126.00-150.00   56
 19  \w     39.00  64.00   0.50    0.20    --   84.34-112.00-180.00   50
 20  \w     34.00  59.00   0.50    0.20    --   58.45-126.00 -90.00   50
 21  \w     25.00  55.00   0.50    0.20    --   58.45-126.00 -30.00   60
 22  \w     43.00  79.00   0.50    0.20    --   76.32 -95.00  30.00   72
 23  \w     31.00  93.00   0.50    0.20    --   76.32-112.00 120.00  124
 24  \w     29.00  54.00   0.50    0.20    --   71.26 -95.00  90.00   50
 25  \w     52.00  91.00   0.50    0.20    --   84.34 -95.00  90.00   78
 26  \w     16.00  42.00   0.50    0.20    --   58.45 -95.00  60.00   52
 27  \w     38.00  63.00   0.50    0.20    --   76.32 -95.00   0.00   50
 28  \w     42.00  88.00   0.50    0.20    --   84.34 -95.00  60.00   92
 29  \w     63.00  90.00   0.50    0.20    --   84.34 -95.00   0.00   54
 30  \w     65.00  91.00   0.50    0.20    --   84.34 -95.00 -30.00   52
 31  \w     29.00  54.00   0.50    0.20    --   71.26 -95.00   0.00   50
 32  \w     47.00  79.00   0.50    0.20    --   84.34 -95.00 -60.00   64
 33  \w     66.00  92.00   0.50    0.20    --   84.34 -95.00-120.00   52
 34  \w     64.00  90.00   0.50    0.20    --   84.34 -95.00-180.00   52
 35  \w     51.00  91.00   0.50    0.20    --   84.34 -95.00-150.00   80
 36  \w     66.00  91.00   0.50    0.20    --   84.34 -95.00 -90.00   50
 37  \w     66.00  91.00   0.50    0.20    --   84.34 -95.00 120.00   50
 38  \w     65.00  90.00   0.50    0.20    --   84.34 -95.00 150.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-R'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
;
 CrysAlisPro convention (1999,Acta A55,543-557)
;
_diffrn_orient_matrix_UB_11      -0.0671119000
_diffrn_orient_matrix_UB_12      -0.0813350000
_diffrn_orient_matrix_UB_13      -0.0622675000
_diffrn_orient_matrix_UB_21      -0.1602589000
_diffrn_orient_matrix_UB_22      0.0303907000
_diffrn_orient_matrix_UB_23      -0.0019033000
_diffrn_orient_matrix_UB_31      0.0821108000
_diffrn_orient_matrix_UB_32      0.1026677000
_diffrn_orient_matrix_UB_33      -0.0374087000
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~2,3~
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            24271
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.247
_diffrn_reflns_theta_min         3.858
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    2.844
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.541
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.43.111a (Rigaku Oxford Diffraction, 2024) Numerical 
 absorption correction based on gaussian integration over a multifaceted 
 crystal model Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_preparation
;
 For data collection the crystal was immersed in a film of perfluoropolyether 
 oil, mounted on a polyimide loop and transferred to stream of cold nitrogen 
 (Oxford Cryostream 800).
;
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexane'
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.872
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.131
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         7613
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0598
_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^)+(0.1405P)^2^] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1768
_refine_ls_wR_factor_ref         0.2151
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5701
_reflns_number_total             7613
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           MaNe018-2_MaNe_a
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_database_code               7133974
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.573
_shelx_estimated_absorpt_t_max   0.895
_shelx_res_checksum              12744
_shelx_hkl_checksum              49041