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_7118772
_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         'C21 H24 N2 O3 S'
_chemical_formula_sum            'C21 H24 N2 O3 S'
_chemical_formula_weight         384.48
_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   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2014-05-22
_audit_creation_method
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_audit_update_record
;
2015-10-17 deposited with the CCDC.
2016-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.3374(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.28349(11)
_cell_length_b                   9.9736(2)
_cell_length_c                   36.4673(6)
_cell_measurement_reflns_used    6744
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      74.3210
_cell_measurement_theta_min      4.5830
_cell_volume                     1920.06(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (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 10.6296
_diffrn_detector_type            'Agilent Diffraction Atlas detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'GV1000, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0948295000
_diffrn_orient_matrix_UB_12      -0.1450822000
_diffrn_orient_matrix_UB_13      -0.0052356000
_diffrn_orient_matrix_UB_21      -0.0443165000
_diffrn_orient_matrix_UB_22      0.0257485000
_diffrn_orient_matrix_UB_23      -0.0414295000
_diffrn_orient_matrix_UB_31      0.2722796000
_diffrn_orient_matrix_UB_32      -0.0463769000
_diffrn_orient_matrix_UB_33      -0.0067078000
_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  0.0292
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13248
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.542
_diffrn_reflns_theta_min         2.425
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_target            Cu
_diffrn_source_type              'Agilent Diffraction microfocus tube'
_exptl_absorpt_coefficient_mu    1.694
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_T_min  0.764
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
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    1.330
_exptl_crystal_description       needle
_exptl_crystal_F_000             816
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: i-PrOH'
_exptl_crystal_size_max          0.3174
_exptl_crystal_size_mid          0.0521
_exptl_crystal_size_min          0.0431
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3838
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0412
_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^)+(0.0569P)^2^+1.1476P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1088
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3468
_reflns_number_total             3838
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc00603e2.cif
_cod_data_source_block           jjshlb
_cod_depositor_comments
'Adding full bibliography for 7118771--7118772.cif.'
_cod_original_cell_volume        1920.06(7)
_cod_database_code               7118772
_nottingham_internal_coll_name   JJSHLB
_nottingham_internal_coll_number 13517
_nottingham_internal_coll_client JJS/HWL
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_method 'omega scans'
_nottingham_internal_coll_frame_time '15.0000, 60.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_user   pczwl
_nottingham_internal_coll_date   14/04/2014
_nottingham_internal_coll_location NOTTS
_nottingham_internal_process_date 15/04/2014
_nottingham_internal_process_user pczwl
_nottingham_internal_solution_date 9/5/2014
_nottingham_internal_solution_user pczwl
_nottingham_internal_refinement_date 9/5/2014
_nottingham_internal_refinement_user pczwl
_nottingham_internal_validation_date 22/5/2014
_nottingham_internal_validation_user pczwl
_nottingham_internal_archive_date 22/5/2014
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C21 H24 N2 O3 S'
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C8(H8), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C21(H21), C22(H22), C23(H23), C24(H24),
 C25(H25)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C)
;
_olex2_exptl_crystal_mounting_method 'in fomblin film on a micromount'