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_7133975
_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
'C52 H56 B2 Cl2 N4, C H2 Cl2, [+ 0.5 DCM squeezed]'
_chemical_formula_sum            'C53.5 H59 B2 Cl5 N4 ed en ez lv so sq t ue'
_chemical_formula_weight         956.91
_chemical_name_systematic        6Bz-Ph
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_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             2023-11-21
_audit_creation_method           'CIF-fill 1.4o (K.Radacki, 2005-23)'
_audit_update_record
;
2024-08-23 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                98.8360(10)
_cell_angle_beta                 91.4760(10)
_cell_angle_gamma                98.891(2)
_cell_formula_units_Z            2
_cell_length_a                   12.6381(3)
_cell_length_b                   12.7947(3)
_cell_length_c                   15.9160(2)
_cell_measurement_reflns_used    13336
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.0070
_cell_measurement_theta_min      2.7840
_cell_volume                     2509.30(9)
_computing_cell_refinement       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.30a (Rigaku OD, 2021)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)''
_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 0.991
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    -97.00 -34.00   0.50    0.38    --  -79.50 115.00 132.73  126
  2  \w   -104.00 -39.00   0.50    0.38    --  -60.16 -15.00 -90.00  130
  3  \w   -117.00 -74.00   0.50    0.38    --  -69.54 -15.00-150.00   86
  4  \w    -72.00 -46.00   0.50    0.38    --  -69.54 -15.00-150.00   52
  5  \w    -64.00 -20.00   0.50    0.38    --  -60.16 126.00-150.00   88
  6  \w   -107.00 -43.00   0.50    0.38    --  -76.37 -15.00  60.00  128
  7  \w   -127.00 -41.00   0.50    0.38    --  -76.37 -15.00 150.00  172
  8  \w     56.00 106.00   0.50    0.38    --   58.45  15.00-150.00  100
  9  \w     48.00 124.00   0.50    0.38    --   76.32  15.00   0.00  152
 10  \w     60.00 118.00   0.50    0.38    --   84.34  15.00  60.00  116
 11  \w     59.00 131.00   0.50    0.38    --   84.34  15.00 120.00  144
 12  \w     57.00 104.00   0.50    0.38    --   58.45  15.00  90.00   94
 13  \w     50.00  90.00   0.50    0.38    --   84.34 -95.00   0.00   80
 14  \w     38.00  92.00   0.50    0.38    --   76.32-112.00   0.00  108
 15  \w     33.00  78.00   0.50    0.38    --   76.32-112.00  60.00   90
 16  \w     43.00  93.00   0.50    0.38    --   76.32-112.00 120.00  100
 17  \w     19.00  48.00   0.50    0.38    --   58.45 -95.00 150.00   58
 18  \w     35.00  61.00   0.50    0.38    --   76.32 -95.00 150.00   52
 19  \w     16.00  58.00   0.50    0.38    --   58.45 -95.00  90.00   84
 20  \w     29.00  55.00   0.50    0.38    --   71.26 -95.00  30.00   52
 21  \w     18.00  54.00   0.50    0.38    --   58.45 -95.00 -30.00   72
 22  \w     31.00  92.00   0.50    0.38    --   76.32-112.00 -90.00  122
 23  \w     43.00  92.00   0.50    0.38    --   84.34 -95.00-150.00   98
 24  \w     20.00  54.00   0.50    0.38    --   58.45 -95.00-150.00   68
 25  \w     29.00  54.00   0.50    0.38    --   71.26 -95.00 -90.00   50
 26  \w     53.00  92.00   0.50    0.38    --   84.34 -95.00 -90.00   78
 27  \w     42.00  92.00   0.50    0.38    --   84.34 -95.00 -60.00  100
 28  \w     65.00  90.00   0.50    0.38    --   84.34 -95.00  30.00   50
 29  \w     46.00  92.00   0.50    0.38    --   84.34 -95.00  60.00   92
 30  \w     66.00  92.00   0.50    0.38    --   84.34 -95.00  90.00   52
 31  \w     67.00  92.00   0.50    0.38    --   84.34 -95.00 150.00   50
 32  \w     51.00  90.00   0.50    0.38    --   84.34 -95.00 120.00   78
 33  \w     67.00  92.00   0.50    0.38    --   84.34 -95.00 -30.00   50
 34  \w     66.00  91.00   0.50    0.38    --   84.34 -95.00-120.00   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      -0.1220333000
_diffrn_orient_matrix_UB_12      -0.0299072000
_diffrn_orient_matrix_UB_13      0.0064461000
_diffrn_orient_matrix_UB_21      -0.0025855000
_diffrn_orient_matrix_UB_22      -0.0928338000
_diffrn_orient_matrix_UB_23      -0.0745668000
_diffrn_orient_matrix_UB_31      0.0190592000
_diffrn_orient_matrix_UB_32      -0.0756829000
_diffrn_orient_matrix_UB_33      0.0633900000
_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  0.0421
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            30823
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.913
_diffrn_reflns_theta_min         2.813
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    2.935
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.754
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.30a (Rigaku Oxford Diffraction, 2021) 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            'clear light yellow'
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_description       plate
_exptl_crystal_F_000             1006
_exptl_crystal_preparation
;
 Crystals were grown at 20 \%C from saturated solution in CD2Cl2. 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: DCM'
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         9719
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0458
_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^)+(0.0649P)^2^+1.0501P] where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1212
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7888
_reflns_number_total             9719
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           JoBo017_JoBo_a_sq
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_original_cell_volume        2509.29(9)
_cod_original_formula_sum        'C53.50 H59 B2 Cl5 N4, [solvent squeezed]'
_cod_database_code               7133975
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.712
_shelx_estimated_absorpt_t_max   0.848
_shelx_res_checksum              88292
_shelx_hkl_checksum              29335
_shelx_fab_checksum              41252