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_7133972
_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         'C34 H24 B2 Cl2, C6 H6'
_chemical_formula_sum            'C40 H30 B2 Cl2'
_chemical_formula_weight         603.16
_chemical_name_systematic        3Bz-Ph
_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            4
_cell_length_a                   13.0142(3)
_cell_length_b                   12.5146(4)
_cell_length_c                   19.1376(7)
_cell_measurement_reflns_used    5981
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.5510
_cell_measurement_theta_min      4.1970
_cell_volume                     3116.89(17)
_computing_cell_refinement       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.68a (Rigaku OD, 2022)'
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
 List of Runs (angles in degrees, time in seconds):
 --------------------------------------------------------------------------
  1  \w    101.00 132.00   0.50    0.93    --   85.25 131.00-174.80   62
  2  \w    101.00 126.00   0.50    0.93    --   85.25 118.00 -82.52   50
  3  \w    100.00 132.00   0.50    0.93    --   85.25 123.00 -53.01   64
  4  \w    105.00 130.00   0.50    0.93    --   85.25 112.00 115.75   50
  5  \w    104.00 129.00   0.50    0.93    --   85.25 112.00   3.05   50
  6  \w    104.00 138.00   0.50    0.93    --   85.25  26.00-123.88   68
  7  \w     52.00  87.00   0.50    0.93    --   85.25 -86.00-102.47   70
  8  \w     45.00  91.00   0.50    0.93    --   85.25-117.00  26.02   92
  9  \w     50.00  91.00   0.50    0.93    --   85.25 -99.00  53.11   82
 10  \w     16.00  66.00   0.50    0.93    --   58.60 -95.00  90.00  100
 11  \w     47.00  73.00   0.50    0.93    --   85.25 -95.00 132.24   52
 12  \w     41.00  83.00   0.50    0.93    --   85.25-102.00  98.28   84
 13  \w     49.00  91.00   0.50    0.93    --   85.25-109.00  86.12   84
 14  \w     61.00  89.00   0.50    0.93    --   82.35 -95.00-120.00   56
 15  \w   -130.00-101.00   0.50    0.93    --  -79.50 -31.00 -45.56   58
 16  \w   -107.00 -72.00   0.50    0.93    --  -58.00 -49.00 -41.16   70
 17  \w   -111.00 -76.00   0.50    0.93    --  -62.00 -50.00-179.78   70
 18  \w   -124.00 -94.00   0.50    0.93    --  -79.50 -64.00-109.78   60
 19  \w   -102.00 -67.00   0.50    0.93    --  -54.00 -52.00  43.59   70
 20  \w   -124.00 -94.00   0.50    0.93    --  -79.50 -64.00  47.53   60
 21  \w   -126.00 -93.00   0.50    0.93    --  -79.50-120.00 -17.58   66
;
_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      0.0247543000
_diffrn_orient_matrix_UB_12      0.0866814000
_diffrn_orient_matrix_UB_13      0.0547350000
_diffrn_orient_matrix_UB_21      -0.0869337000
_diffrn_orient_matrix_UB_22      0.0703660000
_diffrn_orient_matrix_UB_23      -0.0295130000
_diffrn_orient_matrix_UB_31      -0.0763731000
_diffrn_orient_matrix_UB_32      -0.0519550000
_diffrn_orient_matrix_UB_33      0.0511201000
_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  0.0785
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17134
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.070
_diffrn_reflns_theta_min         4.221
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'PhotonJet-R X-ray Source'
_exptl_absorpt_coefficient_mu    2.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 CrysAlisPro 1.171.42.68a (Rigaku Oxford Diffraction, 2022) Empirical 
 absorption correction using spherical harmonics, implemented in SCALE3 
 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_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: C6H6'
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.260
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.02(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     398
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0579
_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^)+(0.0543P)^2^+2.6574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1278
_refine_ls_wR_factor_ref         0.1334
_reflns_Friedel_coverage         0.818
_reflns_Friedel_fraction_full    0.880
_reflns_Friedel_fraction_max     0.872
_reflns_number_gt                4671
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc04433a3.cif
_cod_data_source_block           AlHa036_AlHa_a
_cod_depositor_comments
'Adding full bibliography for 7133971--7133976.cif.'
_cod_database_code               7133972
_shelx_shelxl_version_number     2019/1
_shelx_estimated_absorpt_t_min   0.719
_shelx_estimated_absorpt_t_max   0.835
_shelx_res_checksum              95829
_shelx_hkl_checksum              51807