Asymmetric synthesis of heteroaryl atropisomers via a gold-catalyzed cycloisomerization-amination cascade reaction.
Guo, Rui; Li, Kang-Nan; Liu, Bin; Zhu, Hua-Jie; Fan, Yu-Meng; Gong, Liu-Zhu; Chemical communications (Cambridge, England) 50 (2014) 5451–5454; doi:10.1039/c4cc01397b

data_7112264
_publ_section_title
;
 Asymmetric synthesis of heteroaryl atropisomers via a gold-catalyzed
 cycloisomerization-amination cascade reaction.
;
_journal_issue                   41
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5451
_journal_page_last               5454
_journal_paper_doi               10.1039/c4cc01397b
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C19 H27 B N2 O6'
_chemical_formula_sum            'C19 H27 B N2 O6'
_chemical_formula_weight         390.24
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2013-04-12
_audit_creation_method
;
  Olex2 1.2
  (compiled Mar 21 2013 11:16:32, GUI svn.r4446)
;
_cell_angle_alpha                91.745(2)
_cell_angle_beta                 108.985(3)
_cell_angle_gamma                92.310(3)
_cell_formula_units_Z            2
_cell_length_a                   9.8024(4)
_cell_length_b                   10.2502(3)
_cell_length_c                   11.0769(3)
_cell_measurement_reflns_used    11015
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      69.7085
_cell_measurement_theta_min      4.7736
_cell_volume                     1050.45(6)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      290(2)
_diffrn_detector_area_resol_mean 15.9149
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0146
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            17227
_diffrn_reflns_theta_full        69.84
_diffrn_reflns_theta_max         69.84
_diffrn_reflns_theta_min         4.78
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.750
_exptl_absorpt_correction_T_max  0.8232
_exptl_absorpt_correction_T_min  0.7741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     258
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0448
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0762P)^2^+0.1922P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1269
_refine_ls_wR_factor_ref         0.1295
_reflns_number_gt                3615
_reflns_number_total             3896
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc01397b2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments          'Adding full bibliography for 7112264.cif.'
_cod_database_code               7112264
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H2(0.068) H2A(0.051) H1(0.067) H2B(0.07) H3(0.059) H6(0.055)
 H9A(0.061) H9B(0.061) H10A(0.076) H10B(0.076) H11A(0.126) H11B(0.126)
 H11C(0.126) H13(0.076) H15A(0.164) H15B(0.164) H15C(0.164) H14A(0.137)
 H14B(0.137) H14C(0.137) H17(0.071) H19A(0.152) H19B(0.152) H19C(0.152)
 H18A(0.153) H18B(0.153) H18C(0.153)
 Fixed X: H2(0.8385) H2A(0.1459) H1(0.2098) H2B(0.439) H3(0.6356) H6(0.1761)
 H9A(0.3865) H9B(0.5292) H10A(0.664) H10B(0.5803) H11A(0.4886) H11B(0.4001)
 H11C(0.5504) H13(0.07) H15A(0.2433) H15B(0.1071) H15C(0.0892) H14A(0.2739)
 H14B(0.2186) H14C(0.3542) H17(-0.0084) H19A(0.2278) H19B(0.1235) H19C(0.1744)
 H18A(-0.0756) H18B(-0.1426) H18C(-0.1798)
 Fixed Y: H2(0.0651) H2A(0.1221) H1(-0.3154) H2B(-0.3893) H3(-0.2424) H6(-
 0.096) H9A(0.3633) H9B(0.3837) H10A(0.3445) H10B(0.4732) H11A(0.2379)
 H11B(0.364) H11C(0.3631) H13(0.0109) H15A(0.2092) H15B(0.1391) H15C(0.2278)
 H14A(-0.1147) H14B(-0.0833) H14C(-0.0051) H17(0.4905) H19A(0.5125)
 H19B(0.5923) H19C(0.4575) H18A(0.3638) H18B(0.493) H18C(0.3612)
 Fixed Z: H2(0.204) H2A(-0.0617) H1(0.0661) H2B(0.104) H3(0.1547) H6(0.0853)
 H9A(0.1859) H9B(0.1524) H10A(0.371) H10B(0.3563) H11A(0.4354) H11B(0.4164)
 H11C(0.5244) H13(0.3631) H15A(0.5293) H15B(0.5483) H15C(0.4319) H14A(0.4284)
 H14B(0.5433) H14C(0.5318) H17(-0.1471) H19A(-0.1518) H19B(-0.2589) H19C(-
 0.294) H18A(-0.3907) H18B(-0.3625) H18C(-0.3091)
;