Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles: N- vs. p-aryl-C-nucleophilic substitution.
Dhara, Debabrata; Vijayakanth, Thangavel; Nayak, Mithilesh Kumar; Kalita, Pankaj; Boomishankar, Ramamoorthy; Yildiz, Cem Burak; Chandrasekhar, Vadapalli; Jana, Anukul; Dalton transactions (Cambridge, England : 2003) 47 (2018) 14411–14415; doi:10.1039/c8dt03201g

data_7047501
_publ_section_title
;
 Contrasting reactivity of (boryl)(aryl)lithium-amide with electrophiles:
 N- vs. p-aryl-C-nucleophilic substitution.
;
_journal_issue                   41
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              14411
_journal_page_last               14415
_journal_paper_doi               10.1039/c8dt03201g
_journal_volume                  47
_journal_year                    2018
_chemical_formula_moiety         'C30 H40 B N'
_chemical_formula_sum            'C30 H40 B N'
_chemical_formula_weight         425.44
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-16
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_audit_update_record
;
2018-06-04 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.660(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.626(8)
_cell_length_b                   21.45(2)
_cell_length_c                   13.699(14)
_cell_measurement_reflns_used    5516
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.96
_cell_volume                     2534(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            23780
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.622
_diffrn_reflns_theta_min         1.764
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.063
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0829 before and 0.0746 after correction. The Ratio of minimum to maximum transmission is 0.9120. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     287
_refine_ls_number_reflns         5825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0876
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0644P)^2^+1.3799P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1637
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4142
_reflns_number_total             5825
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt03201g2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7047497--7047501.cif.'
_cod_original_cell_volume        2533(4)
_cod_database_code               7047501
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1I(H1I), C4I(H4I)
2.b Aromatic/amide H refined with riding coordinates:
 C3P(H3P), C4P(H4P), C5P(H5P), C13(H13), C15(H15), N1(H1), C24(H24), C26(H26)
2.c Fitted hexagon refined as free rotating group:
 C1P(C2P,C3P,C4P,C5P,C6P)
2.d Idealised Me refined as rotating group:
 C2I(H2IA,H2IB,H2IC), C3I(H3IA,H3IB,H3IC), C5I(H5IA,H5IB,H5IC), C6I(H6IA,H6IB,
 H6IC), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C),
 C5(H5A,H5B,H5C), C6(H6A,H6B,H6C)
;
_shelx_res_checksum              34971
_olex2_submission_special_instructions 'No special instructions were received'