Synthesis and Isolation of Dinuclear N,C-Chelate Organoboron Compounds Bridged by Neutral, Anionic, and Dianionic 4,4’-Bipyridine via Reductive Coupling of Pyridines
Li, Hai-Jun; Feng, Rui; Shi, Xianghui; Wei, Junnian; Xi, Zhenfeng; Dalton Transactions  (2022) –; doi:10.1039/D2DT02650C

data_7711330
_publ_section_title
;
 Synthesis and Isolation of Dinuclear N,C-Chelate Organoboron Compounds
 Bridged by Neutral, Anionic, and Dianionic 4,4&#x2019;-Bipyridine via
 Reductive Coupling of Pyridines
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT02650C
_journal_year                    2022
_chemical_formula_moiety
'C18 H36 K N2 O6, C58 H58 B2 N2, 2(C4 H8 O), [+ solvents]'
_chemical_formula_sum            'C80 H102 B2 K N4 O7'
_chemical_formula_weight         1292.37
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-02-16
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2022-06-22 deposited with the CCDC.	2022-09-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.383(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.8912(4)
_cell_length_b                   26.8301(7)
_cell_length_c                   22.9414(6)
_cell_measurement_reflns_used    29346
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      28.2630
_cell_measurement_theta_min      2.1650
_cell_volume                     8159.8(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      180.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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    -56.00 -22.00   0.50    6.00    --  -16.00 -77.00  60.00   68
  2  \w   -104.00 -71.00   0.50    6.00    --  -16.00 -77.00  60.00   66
  3  \w    -77.00  36.00   0.50    6.00    --  -16.00  37.00 -60.00  226
  4  \w    -70.00  24.00   0.50    6.00    --  -16.00 -77.00  90.00  188
  5  \w   -105.00 -20.00   0.50    6.00    --  -16.00 -57.00   0.00  170
  6  \w      3.00  47.00   0.50    6.00    --   16.20  77.00 -60.00   88
  7  \w     80.00 105.00   0.50    6.00    --   16.20  77.00-120.00   50
  8  \w     16.00  51.00   0.50    6.00    --   16.20  77.00-120.00   70
  9  \w    -31.00  60.00   0.50    6.00    --   16.20 -82.00   0.00  182
 10  \w    -49.00  46.00   0.50    6.00    --   16.20 -57.00 120.00  190
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0356423000
_diffrn_orient_matrix_UB_12      -0.0186248000
_diffrn_orient_matrix_UB_13      -0.0009915000
_diffrn_orient_matrix_UB_21      0.0262856000
_diffrn_orient_matrix_UB_22      0.0174314000
_diffrn_orient_matrix_UB_23      -0.0128442000
_diffrn_orient_matrix_UB_31      0.0300008000
_diffrn_orient_matrix_UB_32      0.0069062000
_diffrn_orient_matrix_UB_33      0.0297572000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            100990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.009
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.052
_exptl_crystal_description       block
_exptl_crystal_F_000             2780
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     859
_refine_ls_number_reflns         16076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0780P)^2^+2.7335P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1406
_refine_ls_wR_factor_ref         0.1483
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12900
_reflns_number_total             16076
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2dt02650c2.cif
_cod_data_source_block           exp_6238
_cod_database_code               7711330
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N B K'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.970
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C69(H6,H7), C70(H8,H9), C68(H17,H18), C67(H19,H20), C64(H34,H35), C74(H36,
 H37), C61(H38,H39), C75(H40,H41), C62(H42,H43), C76(H44,H45), C73(H46,H47),
 C63(H48,H49), C66(H53,H54), C72(H55,H56), C71(H57,H58), C59(H59,H60), C60(H61,
 H62), C65(H63,H64), C92(H92A,H92B), C91(H91A,H91B), C94(H94A,H94B), C93(H93A,
 H93B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H), C1(HA), C34(HB), C32(HC), C4(HD), C31(HE), C7(HF), C14(HG), C16(HH),
 C10(HI), C9(HJ), C8(HK), C23(HL), C25(HM), C37(HN), C40(HU), C39(H2), C55(H3),
 C53(H4), C38(H5), C44(H10), C46(H30)
2.c Idealised Me refined as rotating group:
 C30(HO,HP,HQ), C18(HR,HS,HT), C20(HV,HW,HX), C27(HY,HZ,H1), C29(H11,H12,H13),
 C50(H14,H15,H16), C28(H21,H22,H23), C57(H24,H25,H26), C48(H27,H28,H29),
 C19(H31,H32,H33), C58(H50,H51,H52), C49(H65,H66,H67)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              3203
_shelx_hkl_checksum              85997
_shelx_fab_checksum              3066
_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 1.337
_oxdiff_exptl_absorpt_empirical_full_min 0.807