A cooperative Pd/Co catalysis for the asymmetric (4+2) cycloaddition of vinyl benzoxazinones with N-acylpyrazoles
Xiong, Wei; Jiang, Xuan; Zhang, Mao-Mao; Xiao, Wen-Jing; Lu, Liang-Qiu; Chemical Communications  (2021) –; doi:10.1039/D1CC05952A

data_7129280
_publ_section_title
;
 A cooperative Pd/Co catalysis for the asymmetric (4+2) cycloaddition of
 vinyl benzoxazinones with N-acylpyrazoles
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05952A
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H25 N3 O3 S'
_chemical_formula_sum            'C24 H25 N3 O3 S'
_chemical_formula_weight         435.53
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-31
_audit_creation_method
;
Olex2 1.3-alpha
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2021-10-07 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.45794(11)
_cell_length_b                   11.87783(15)
_cell_length_c                   22.4725(3)
_cell_measurement_reflns_used    13003
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.5450
_cell_measurement_theta_min      1.9450
_cell_volume                     2257.63(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -66.00  33.00   1.00    1.00    --  -40.98  38.00-180.00   99
  2  \w   -117.00  -8.00   1.00    1.00    --  -40.98 -77.00-150.00  109
  3  \w      2.00  82.00   1.00    1.00    --   40.98-100.00  90.00   80
  4  \w     81.00 178.00   1.00    1.03    --  106.95  45.00 150.00   97
  5  \w     34.00 133.00   1.00    1.03    --  106.95 -45.00 150.00   99
  6  \w     81.00 178.00   1.00    1.03    --  106.95  45.00 -60.00   97
  7  \w     25.00 109.00   1.00    1.03    --  106.95 -95.00   0.00   84
  8  \w     35.00 136.00   1.00    1.03    --  106.95 -61.00   0.00  101
  9  \w   -113.00 -71.00   1.00    1.00    --  -40.98 -57.00  60.00   42
 10  \w    151.00 177.00   1.00    1.03    --  106.95 112.00-150.00   26
 11  \w    115.00 140.00   1.00    1.03    --  106.95  45.00-150.00   25
 12  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00  90.00  100
 13  \w   -113.00 -13.00   1.00    1.00    --  -41.23 -57.00 -60.00  100
 14  \w     25.00  99.00   1.00    1.00    --   41.23-127.00 -30.00   74
 15  \w     31.00 116.00   1.00    1.03    --  106.95-112.00-150.00   85
 16  \w     79.00 168.00   1.00    1.03    --  106.95  30.00-120.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0349166000
_diffrn_orient_matrix_UB_12      -0.1115239000
_diffrn_orient_matrix_UB_13      -0.0324478000
_diffrn_orient_matrix_UB_21      -0.0167108000
_diffrn_orient_matrix_UB_22      -0.0602666000
_diffrn_orient_matrix_UB_23      0.0603818000
_diffrn_orient_matrix_UB_31      -0.1779532000
_diffrn_orient_matrix_UB_32      0.0275460000
_diffrn_orient_matrix_UB_33      0.0006883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0299
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16823
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.613
_diffrn_reflns_theta_min         3.934
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.281
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Flack x determined using 1802 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.036(8)
_refine_ls_extinction_coef       0.154(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     300
_refine_ls_number_reflns         4484
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0648P)^2^+0.1011P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0949
_refine_ls_wR_factor_ref         0.0964
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                4371
_reflns_number_total             4484
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05952a2.cif
_cod_data_source_block           exp_2092
_cod_database_code               7129280
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C10(H10), C11(H11), C12(H12), C17(H17), C20(H20), C13(H13),
 C14(H14), C18(H18), C2(H2)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C23(H23A,H23B,H23C)
;
_shelx_res_checksum              30357
_shelx_hkl_checksum              97058
_olex2_date_sample_data_collection 2019-12-31
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.645
_oxdiff_exptl_absorpt_empirical_full_min 0.606