Catalytic asymmetric conjugate addition of coumarins to unsaturated ketones catalyzed by a chiral-at-metal Rh(III) complex.
Chen, Xiangjie; Zhao, Yujie; Huang, Cheng; Zhao, Zhifei; Zhao, Weiwei; Li, Shi-Wu; Chemical communications (Cambridge, England) 60 (2023) 236–239; doi:10.1039/d3cc04726a

data_7132391
_publ_section_title
;
 Catalytic asymmetric conjugate addition of coumarins to unsaturated
 ketones catalyzed by a chiral-at-metal Rh(III) complex.
;
_journal_issue                   2
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              236
_journal_page_last               239
_journal_paper_doi               10.1039/d3cc04726a
_journal_volume                  60
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C24 H18 Br N3 O3'
_chemical_formula_sum            'C24 H18 Br N3 O3'
_chemical_formula_weight         476.32
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2022-12-28
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-02-27 deposited with the CCDC.	2023-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.11185(14)
_cell_length_b                   13.81714(17)
_cell_length_c                   15.0875(2)
_cell_measurement_reflns_used    7937
_cell_measurement_temperature    220.00(10)
_cell_measurement_theta_max      73.6190
_cell_measurement_theta_min      4.3020
_cell_volume                     2107.98(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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      220.00(10)
_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 0.992
_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   -115.00 -17.00   1.00    1.00    --  -40.92 -37.00 -30.00   98
  2  \w     23.00  97.00   1.00    1.00    --   40.92-125.00  30.00   74
  3  \w      1.00  82.00   1.00    1.00    --   40.92 -99.00 -90.00   81
  4  \w     34.00 122.00   1.00    1.37    --  107.58-125.00 -30.00   88
  5  \w     94.00 178.00   1.00    1.37    --  107.58 125.00-150.00   84
  6  \w     83.00 178.00   1.00    1.37    --  107.58  35.00  -5.00   95
  7  \w     79.00 178.00   1.00    1.37    --  107.58  30.00  60.00   99
  8  \w     31.00 140.00   1.00    1.37    --  107.58 -77.00 120.00  109
  9  \w   -115.00 -17.00   1.00    1.00    --  -40.92 -37.00-120.00   98
 10  \w   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00-180.00  100
 11  \w     82.00 100.00   1.00    1.37    --  107.58  45.00 150.00   18
;
_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      -0.0452200000
_diffrn_orient_matrix_UB_12      0.0053521000
_diffrn_orient_matrix_UB_13      -0.0974438000
_diffrn_orient_matrix_UB_21      0.1289571000
_diffrn_orient_matrix_UB_22      -0.0500348000
_diffrn_orient_matrix_UB_23      -0.0291871000
_diffrn_orient_matrix_UB_31      -0.0672657000
_diffrn_orient_matrix_UB_32      -0.0994662000
_diffrn_orient_matrix_UB_33      0.0094400000
_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  0.0294
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11365
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.750
_diffrn_reflns_theta_min         4.339
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.922
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52863
_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            'light colourless'
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1625 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.019(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4198
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0304
_refine_ls_R_factor_gt           0.0281
_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^)+(0.0378P)^2^+0.1959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0707
_reflns_Friedel_coverage         0.739
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3983
_reflns_number_total             4198
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc04726a2.cif
_cod_data_source_block           24b
_cod_depositor_comments          'Adding full bibliography for 7132391.cif.'
_cod_database_code               7132391
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18),
 C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_shelx_res_checksum              99931
_olex2_date_sample_data_collection 2022-12-28
_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 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.534