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_7047499
_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 H39 B Cl3 N Si, C3 H7'
_chemical_formula_sum            'C33 H46 B Cl3 N Si'
_chemical_formula_weight         601.96
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -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
;
2018-06-07 deposited with the CCDC.
2018-09-10 downloaded from the CCDC.
;
_cell_angle_alpha                99.984(6)
_cell_angle_beta                 99.791(6)
_cell_angle_gamma                93.044(8)
_cell_formula_units_Z            2
_cell_length_a                   9.180(3)
_cell_length_b                   13.123(4)
_cell_length_c                   14.146(4)
_cell_measurement_reflns_used    3063
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      23.358
_cell_measurement_theta_min      2.47
_cell_volume                     1647.9(9)
_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 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f 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  0.0831
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            27921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.700
_diffrn_reflns_theta_min         1.487
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.337
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0710 before and 0.0627 after correction. The Ratio of minimum to maximum transmission is 0.9005. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             642
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.831
_refine_diff_density_min         -0.887
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0056(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         7616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0625
_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^)+(0.0737P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1476
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4737
_reflns_number_total             7616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt03201g2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7047497--7047501.cif.'
_cod_original_cell_volume        1648.0(8)
_cod_database_code               7047499
_shelx_shelxl_version_number     2016/4
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.957
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,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:
 C21(H21), C61(H61)
2.b Secondary CH2 refined with riding coordinates:
 C3S(H3SA,H3SB), C1S(H1SA,H1SB)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C9P(H9P), C3(H3), C11P(H11P), C5P(H5P), C3P(H3P)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C15(H15A,H15B,H15C), C10(H10A,H10B,H10C), C12(H12A,H12B,
 H12C), C13(H13A,H13B,H13C), C63(H63A,H63B,H63C), C23(H23A,H23B,H23C), C14(H14A,
 H14B,H14C), C62(H62A,H62B,H62C), C11(H11A,H11B,H11C), C2S(H2SA,H2SB,H2SC)
;
_shelx_res_checksum              76160
_olex2_submission_special_instructions 'No special instructions were received'