Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines.
Smith, Joshua J.; Best, Daniel; Lam, Hon Wai; Chemical communications (Cambridge, England) 52 (2016) 3770–3772; doi:10.1039/c6cc00603e

data_7118771
_publ_section_title
;
 Copper-catalyzed borylative coupling of vinylazaarenes and N-Boc imines.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3770
_journal_page_last               3772
_journal_paper_doi               10.1039/c6cc00603e
_journal_volume                  52
_journal_year                    2016
_chemical_formula_moiety         'C23 H26 N2 O3'
_chemical_formula_sum            'C23 H26 N2 O3'
_chemical_formula_weight         378.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-11-25
_audit_creation_method
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Olex2 1.2
(compiled 2013.11.15 svn.r2834 for OlexSys, GUI svn.r4715)
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_audit_update_record
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2015-10-17 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.625(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.1957(2)
_cell_length_b                   24.5851(11)
_cell_length_c                   16.0276(7)
_cell_measurement_reflns_used    3187
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3430
_cell_measurement_theta_min      3.2820
_cell_volume                     2043.22(15)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
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_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2013 (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 10.3271
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1838179000
_diffrn_orient_matrix_UB_12      0.0426871000
_diffrn_orient_matrix_UB_13      -0.0337312000
_diffrn_orient_matrix_UB_21      0.2092102000
_diffrn_orient_matrix_UB_22      -0.0439857000
_diffrn_orient_matrix_UB_23      -0.0063128000
_diffrn_orient_matrix_UB_31      -0.1038158000
_diffrn_orient_matrix_UB_32      -0.0129309000
_diffrn_orient_matrix_UB_33      -0.0899867000
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0695
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7657
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.492
_diffrn_reflns_theta_min         3.296
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    0.654
_exptl_absorpt_correction_T_max  1.267
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28a (release 18-03-2013 CrysAlis171 .NET)
(compiled Mar 18 2013,11:47:30)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_description       needle
_exptl_crystal_F_000             808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: CHCl3, petroleum ether 40-60'
_exptl_crystal_size_max          0.3595
_exptl_crystal_size_mid          0.0313
_exptl_crystal_size_min          0.026
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.533
_refine_diff_density_rms         0.075
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4024
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0981
_refine_ls_R_factor_gt           0.0749
_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^)+(0.1350P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1999
_refine_ls_wR_factor_ref         0.2229
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2940
_reflns_number_total             4024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00603e2.cif
_cod_data_source_block           jjshla
_cod_depositor_comments
'Adding full bibliography for 7118771--7118772.cif.'
_cod_database_code               7118771
_nottingham_internal_coll_name   JJSHLA
_nottingham_internal_coll_number 13051
_nottingham_internal_coll_client JJS/HWL
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_frame_time '75 and 300S'
_nottingham_internal_coll_frame_width 1
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_date   22/11/2013
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_user WL
_nottingham_internal_process_date 25/11/2013
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 25/11/2013
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 25/11/2013
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 25/11/2013
_nottingham_internal_archive_date 25/11/2013
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C23 H26 N2 O3'
_chemical_oxdiff_usercomment
'JJSHLA #13051 IN FOMBLIN FILM ON A MICROMOUNT FOR JJS/HWL'
_reflns_odcompleteness_completeness 99.18
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.13
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;