A second-generation ligand for the enantioselective rhodium-catalyzed addition of arylboronic acids to alkenylazaarenes
Iain D. Roy; Alan R. Burns; Graham Pattison; Boris Michel; Alexandra J. Parker; Hon Wai Lam; Chem.Commun. 50 (2014) 2865–; doi:10.1039/c4cc00340c

data_7112066
_publ_section_title
;
 A second-generation ligand for the enantioselective rhodium-catalyzed
 addition of arylboronic acids to alkenylazaarenes
;
_journal_name_full               Chem.Commun.
_journal_page_first              2865
_journal_paper_doi               10.1039/c4cc00340c
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C10 H10 N4'
_chemical_formula_sum            'C10 H10 N4'
_chemical_formula_weight         186.22
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.3737(2)
_cell_length_b                   8.5684(2)
_cell_length_c                   23.0087(6)
_cell_measurement_reflns_used    8026
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.7400
_cell_measurement_theta_min      3.6510
_cell_volume                     1848.00(8)
_computing_cell_refinement       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_collection       'CrysAlisPro (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlisPro (Agilent Technologies, 2011)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008) and local programs'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 10.3147
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Agilent Technologies SuperNova'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0319
_diffrn_reflns_av_unetI/netI     0.0214
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19622
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.091
_diffrn_reflns_theta_min         2.803
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  2.680
_exptl_absorpt_correction_T_min  1.468
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Numerical absorption correction based on gaussian integration over
   a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.584
_exptl_crystal_size_mid          0.532
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.0033(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0431
_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^)+(0.0533P)^2^+0.7566P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1105
_refine_ls_wR_factor_ref         0.1172
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2373
_reflns_number_total             2795
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc00340c.txt
_cod_data_source_block           hl3010
_cod_database_code               7112066
_shelx_estimated_absorpt_t_min   0.951
_shelx_estimated_absorpt_t_max   0.980
_shelxl_version_number           2013-2
_shelx_res_checksum              52077
_shelx_hkl_checksum              27004