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_7133971
_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_absolute_configuration unknown
_chemical_formula_moiety         'C18 H24 B2 Cl2'
_chemical_formula_sum            'C18 H24 B2 Cl2'
_chemical_formula_weight         332.89
_chemical_name_systematic        3Bz-Et
_chemical_properties_physical    Air-sensitive,Moisture-sensitive
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-03-28
_audit_creation_method           'CIF-fill 1.4t (K.Radacki, 2005-23)'
_audit_update_record
;
2024-08-23 deposited with the CCDC.	2024-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.1263(2)
_cell_length_b                   8.8273(2)
_cell_length_c                   26.4394(4)
_cell_measurement_reflns_used    12575
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.6690
_cell_measurement_theta_min      3.2400
_cell_volume                     3530.30(11)
_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-2019/1 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/1 (Sheldrick, 2019)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w     22.00  47.00   0.50    0.05    --   58.75-103.00 102.00   50
  2  \w    -43.00 -16.00   0.50    0.05    --  -60.36 103.00-155.00   54
  3  \w    -78.00 -53.00   0.50    0.05    --  -69.85 103.00-155.00   50
  4  \w     32.00  57.00   0.50    0.05    --   71.46-103.00 102.00   50
  5  \w     59.00  84.00   0.50    0.05    --   76.32-103.00 102.00   50
  6  \w    -89.00 -42.00   0.50    0.05    --  -76.37 103.00-155.00   94
  7  \w     42.00  67.00   0.50    0.05    --   84.34-103.00 102.00   50
  8  \w     20.00  63.00   0.50    0.05    --   58.75-126.00   0.00   86
  9  \w     16.00  42.00   0.50    0.05    --   58.75 -95.00-150.00   52
 10  \w   -111.00 -35.00   0.50    0.05    --  -60.36 -15.00   0.00  152
 11  \w     30.00  71.00   0.50    0.05    --   71.46 -95.00-150.00   82
 12  \w     32.00  63.00   0.50    0.05    --   76.32-112.00 -60.00   62
 13  \w     35.00  71.00   0.50    0.05    --   76.32 -95.00 -30.00   72
 14  \w     44.00  82.00   0.50    0.05    --   76.32 -95.00  30.00   76
 15  \w    -71.00 -45.00   0.50    0.05    --  -76.37 -15.00-120.00   52
 16  \w   -126.00 -81.00   0.50    0.05    --  -76.37 -15.00-120.00   90
 17  \w     39.00  76.00   0.50    0.05    --   84.34-112.00  90.00   74
 18  \w     61.00 105.00   0.50    0.05    --   84.34  15.00-180.00   88
;
_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      0.0002718000
_diffrn_orient_matrix_UB_12      0.0307154000
_diffrn_orient_matrix_UB_13      0.1482670000
_diffrn_orient_matrix_UB_21      -0.0559491000
_diffrn_orient_matrix_UB_22      0.0414263000
_diffrn_orient_matrix_UB_23      -0.0766607000
_diffrn_orient_matrix_UB_31      -0.0851255000
_diffrn_orient_matrix_UB_32      -0.0271333000
_diffrn_orient_matrix_UB_33      0.0507951000
_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  0.0394
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            16689
_diffrn_reflns_point_group_measured_fraction_full 0.871
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.059
_diffrn_reflns_theta_min         3.343
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    3.217
_exptl_absorpt_correction_T_max  0.966
_exptl_absorpt_correction_T_min  0.498
_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            colourless
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_preparation
;
 Crystals were grown at -30 \%C from saturated solution in pentane. 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: pentane'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.103(16)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     406
_refine_ls_number_reflns         5740
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0346
_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^)+(0.0670P)^2^+0.2414P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0980
_refine_ls_wR_factor_ref         0.0992
_reflns_Friedel_coverage         0.687
_reflns_Friedel_fraction_full    0.737
_reflns_Friedel_fraction_max     0.714
_reflns_number_gt                5459
_reflns_number_total             5740
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           JoBo012_JoBo_a
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_original_cell_volume        3530.31(11)
_cod_database_code               7133971
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.445
_shelx_estimated_absorpt_t_max   0.627
_shelx_res_checksum              85256
_shelx_hkl_checksum              24703