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_1570141
_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         'C12 H23 B2 I N5, I'
_chemical_formula_sum            'C12 H23 B2 I2 N5'
_chemical_formula_weight         512.77
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-08-09 deposited with the CCDC.	2023-10-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.321(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2464(16)
_cell_length_b                   14.259(2)
_cell_length_c                   13.0316(19)
_cell_measurement_reflns_used    1533
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      30.98
_cell_measurement_theta_min      2.99
_cell_volume                     1852.7(5)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_collection       'GDA - generic data acquisition software'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Photon counting pixel array'
_diffrn_detector_type            'Dectris PILATUS 2M'
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measurement_device       'Fixed \c 3-circle diffractometer'
_diffrn_measurement_device_type  'Fluid Film Devices'
_diffrn_measurement_method       'shutterless scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroMount'
_diffrn_radiation_monochromator  'Silicon 111'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     1.0402
_diffrn_reflns_av_R_equivalents  0.0821
_diffrn_reflns_av_unetI/netI     0.0933
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6651
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        31.662
_diffrn_reflns_theta_max         31.662
_diffrn_reflns_theta_min         2.990
_diffrn_source                   Synchrotron
_diffrn_source_current           0.0
_diffrn_source_details           'Allan et al. (2017)'
_diffrn_source_power             0.0
_diffrn_source_type              'Diamond Light Source Beamline I19-1'
_diffrn_source_voltage           0.0
_diffrn_standards_number         0
_entry.id                        xia2
_exptl_absorpt_coefficient_mu    10.039
_exptl_absorpt_correction_T_max  0.4337
_exptl_absorpt_correction_T_min  0.1669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1533 before and 0.0813 after correction.
The Ratio of minimum to maximum transmission is 0.3848.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_description       plate
_exptl_crystal_F_000             984
_exptl_crystal_recrystallization_method
'The material was recrystallised from Difluorobenzene by slow cooling'
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.013
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.778
_refine_diff_density_min         -1.357
_refine_diff_density_rms         0.267
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         1936
_refine_ls_number_restraints     164
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0778
_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^)+(0.1510P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2051
_refine_ls_wR_factor_ref         0.2213
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1306
_reflns_number_total             1936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04269c2.cif
_cod_data_source_block           mi22013
_cod_depositor_comments
'Adding full bibliography for 1570141--1570144.cif.'
_cod_database_code               1570141
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.906
_shelx_estimated_absorpt_t_min   0.634
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H) groups, All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B2-H2A = B1-H1A
 1 with sigma of 0.02
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C11(H11A,H11B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6)
4.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              61252
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in Paratone oil'
_olex2_submission_original_sample_id CM174
_olex2_submission_special_instructions 'No special instructions were received'