Borylation directed borylation of <i>N</i>-alkyl anilines using iodine activated pyrazaboles.
Millet, C. R. P.; Noone, E.; Schellbach, A. V.; Pahl, J.; Łosiewicz, J; Nichol, G. S.; Ingleson, M. J.; Chemical science 14 (2023) 12041–12048; doi:10.1039/d3sc04269c

data_1570142
_publ_section_title
;
 Borylation directed borylation of <i>N</i>-alkyl anilines using iodine
 activated pyrazaboles.
;
_journal_issue                   43
_journal_name_full               'Chemical science'
_journal_page_first              12041
_journal_page_last               12048
_journal_paper_doi               10.1039/d3sc04269c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C6 H8 B2 I2 N4'
_chemical_formula_sum            'C6 H8 B2 I2 N4'
_chemical_formula_weight         411.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-08-09
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                102.544(7)
_cell_angle_beta                 91.351(5)
_cell_angle_gamma                112.430(7)
_cell_formula_units_Z            2
_cell_length_a                   7.6116(5)
_cell_length_b                   7.7121(7)
_cell_length_c                   10.8808(7)
_cell_measurement_reflns_used    3217
_cell_measurement_temperature    120.00(10)
_cell_measurement_theta_max      28.4880
_cell_measurement_theta_min      3.8800
_cell_volume                     572.28(8)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120.00
_diffrn_detector_area_resol_mean 5.1574
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_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    -63.00  -6.00   1.00   30.00    --  -15.73  99.00 -49.00   57
  2  \w    -15.00  64.00   1.00   30.00    --   16.98 -99.00-156.00   79
  3  \w    -42.00  24.00   1.00   30.00    --  -15.73 -77.00-180.00   66
  4  \w    -15.00  64.00   1.00   30.00    --   16.98 -99.00 -90.00   79
  5  \w    -67.00  54.00   1.00   30.00    --   16.98 -38.00 -60.00  121
  6  \w    -15.00  64.00   1.00   30.00    --   16.98 -99.00 -30.00   79
  7  \w    -42.00  56.00   1.00   30.00    --   16.98 -77.00  60.00   98
  8  \w    -42.00  24.00   1.00   30.00    --  -15.73 -77.00  30.00   66
  9  \w    -42.00   2.00   1.00   30.00    --  -15.73 -77.00 120.00   44
 10  \w   -100.00  21.00   1.00   30.00    --  -15.73 -57.00 -30.00  121
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4678
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.878
_diffrn_reflns_theta_min         3.222
_exptl_absorpt_coefficient_mu    5.461
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67027
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.389
_exptl_crystal_description       block
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.163
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.029
_refine_diff_density_max         1.196
_refine_diff_density_min         -0.863
_refine_diff_density_rms         0.161
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0379
_refine_ls_R_factor_gt           0.0294
_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^)+(0.0422P)^2^+0.5421P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4005
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2\s(I)'
_twin_special_details
;
Component 2 rotated by 179.9668\% 
 around [0.00 1.00 0.00] (reciprocal) or [0.36 0.92 0.15] (direct)
;
_cod_data_source_file            d3sc04269c2.cif
_cod_data_source_block           mi19017_mo_2comp_refinalized_twin1_hklf4
_cod_depositor_comments
'Adding full bibliography for 1570141--1570144.cif.'
_cod_database_code               1570142
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5396(9)
 0.4604(9)
2. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups
3.a Ternary CH refined with riding coordinates:
 B2(H2A), B1(H1A)
3.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C2(H2), C5(H5), C1(H1), C3(H3)
;
_shelx_res_checksum              34861
_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
;