Copper-Catalyzed Borylative Cyclization of in Situ Generated o-Allenylaryl Nitriles with Bis(pinacolato)diboron.
Xiong, Meijun; Xie, Xin; Liu, Yuanhong; Organic letters 19 (2017) 3398–3401; doi:10.1021/acs.orglett.7b01355

data_1546409
_publ_section_title
;
 Copper-Catalyzed Borylative Cyclization of in Situ Generated
 o-Allenylaryl Nitriles with Bis(pinacolato)diboron.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3398
_journal_page_last               3401
_journal_paper_doi               10.1021/acs.orglett.7b01355
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C32 H40 B N O3 Si'
_chemical_formula_sum            'C32 H40 B N O3 Si'
_chemical_formula_weight         525.55
_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     direct
_audit_creation_date             2015-09-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.456(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.188(3)
_cell_length_b                   10.6143(18)
_cell_length_c                   13.479(2)
_cell_measurement_reflns_used    1346
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      19.49
_cell_measurement_theta_min      2.44
_cell_volume                     2887.4(8)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      130
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0922
_diffrn_reflns_av_unetI/netI     0.0892
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19290
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         2.018
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6735
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0697 before and 0.0541 after correction.
The Ratio of minimum to maximum transmission is 0.9033.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_description       block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.983
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     353
_refine_ls_number_reflns         5298
_refine_ls_number_restraints     108
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1680
_refine_ls_R_factor_gt           0.0987
_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^)+(0.1702P)^2^+4.1632P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2578
_refine_ls_wR_factor_ref         0.3189
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2864
_reflns_number_total             5298
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01355_si_002.cif
_cod_data_source_block           dm15694
_cod_depositor_comments
'Adding full bibliography for 1546408--1546409.cif.'
_cod_database_code               1546409
_shelxl_version_number           2014-3
_shelx_estimated_absorpt_t_max   0.994
_shelx_estimated_absorpt_t_min   0.977
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Si1 \\sim C21 \\sim C22: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
C23 \\sim C24 \\sim C25 \\sim C26: within 2A with sigma of 0.005 and sigma for
terminal atoms of 0.01
C27 \\sim C28 \\sim C29: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
C30 \\sim C31 \\sim C32: within 2A with sigma of 0.005 and sigma for terminal
atoms of 0.01
Uanis(C29) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C32) \\sim Ueq, Uanis(C31)
\\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C24) \\sim Ueq,
Uanis(C26) \\sim Ueq, Uanis(C25) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Rotating group:
 N1(H1A,H1B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C19(H19)
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C26(H26A,H26B,H26C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C31(H31A,
 H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_res_checksum              3800
_shelx_hkl_checksum              36102
_olex2_submission_special_instructions 'No special instructions were received'