Iridium and a Brønsted acid cooperatively catalyzed chemodivergent and stereoselective reactions of vinyl benzoxazinones with azlactones.
Sun, Meng; Wan, Xiao; Zhou, Si-Jia; Mei, Guang-Jian; Shi, Feng; Chemical communications (Cambridge, England)  (2019) –; doi:10.1039/c8cc08962k

data_7122813
_publ_section_title
;
 Iridium and a Br\/onsted acid cooperatively catalyzed chemodivergent and
 stereoselective reactions of vinyl benzoxazinones with azlactones.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/c8cc08962k
_journal_year                    2019
_chemical_formula_moiety         'C28 H26 N2 O6 S'
_chemical_formula_sum            'C28 H26 N2 O6 S'
_chemical_formula_weight         518.57
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-12-02
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3461 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-10-21 deposited with the CCDC.
2019-01-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.409(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.4926(15)
_cell_length_b                   12.1584(19)
_cell_length_c                   22.925(4)
_cell_measurement_reflns_used    7470
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.37
_cell_measurement_theta_min      2.26
_cell_volume                     2638.1(7)
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_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  0.0790
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17967
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.392
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.167
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5578
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.306
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5729
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0555
_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^)+(0.0883P)^2^+0.6652P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1512
_refine_ls_wR_factor_ref         0.1626
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4365
_reflns_number_total             5729
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08962k2.cif
_cod_data_source_block           mgj_20171201_m17_0m
_cod_database_code               7122813
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.944
_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
2.a Ternary CH refined with riding coordinates:
 C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), C6(H6), C7(H7), C8(H8), C9(H9), C11(H11), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27)
2.d X=CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.e Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              27238
_olex2_submission_special_instructions 'No special instructions were received'