A chiral-at-metal asymmetric catalyzed vinylogous Michael addition of ortho-methyl aromatic nitro compounds for isoxazole derivative synthesis
Li, Shi-Wu; Du, Yu; Kang, Qiang; Organic Chemistry Frontiers 6 (2019) 2775–; doi:10.1039/C9QO00676A

data_1554997
_publ_section_title
;
 A chiral-at-metal asymmetric catalyzed vinylogous Michael addition of
 ortho-methyl aromatic nitro compounds for isoxazole derivative synthesis
;
_journal_issue                   15
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2775
_journal_paper_doi               10.1039/C9QO00676A
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C21 H18 N4 O4 S'
_chemical_formula_weight         422.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-03-18 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0211(2)
_cell_length_b                   16.1241(5)
_cell_length_c                   20.6340(5)
_cell_measurement_reflns_used    9862
_cell_measurement_temperature    127(2)
_cell_measurement_theta_max      72.24
_cell_measurement_theta_min      3.48
_cell_volume                     2003.25(10)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      127(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0657
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16910
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         3.479
_exptl_absorpt_coefficient_mu    1.753
_exptl_absorpt_correction_T_max  0.7521
_exptl_absorpt_correction_T_min  0.3203
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         1.320
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1125 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.018(13)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3543
_refine_ls_number_restraints     15
_refine_ls_restrained_S_all      1.077
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0916
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1198P)^2^+5.2408P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2275
_refine_ls_wR_factor_ref         0.2394
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                3084
_reflns_number_total             3543
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00676a2.cif
_cod_data_source_block           Compound
_cod_database_code               1554997
_shelx_shelxl_version_number     2018/3
_shelx_res_checksum              26056
_shelx_hkl_checksum              17708