Three-Component Catalytic Carboxygenation of Activated Alkenes Enabled by Bimetallic Rh(III)/Cu(II) Catalysis.
Zhang, Shang-Shi; Xia, Jie; Wu, Jia-Qiang; Liu, Xu-Ge; Zhou, Chu-Jun; Lin, E.; Li, Qingjiang; Huang, Shi-Liang; Wang, Honggen; Organic letters 19 (2017) 5868–5871; doi:10.1021/acs.orglett.7b02846

data_1547734
_publ_section_title
;
 Three-Component Catalytic Carboxygenation of Activated Alkenes Enabled by
 Bimetallic Rh(III)/Cu(II) Catalysis.
;
_journal_issue                   21
_journal_name_full               'Organic letters'
_journal_page_first              5868
_journal_page_last               5871
_journal_paper_doi               10.1021/acs.orglett.7b02846
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C24 H30 N4 O2'
_chemical_formula_sum            'C24 H30 N4 O2'
_chemical_formula_weight         406.52
_space_group_crystal_system      tetragonal
_space_group_IT_number           82
_space_group_name_Hall           'I -4'
_space_group_name_H-M_alt        'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_space_group_name_H-M   'I -4'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.5556(5)
_cell_length_b                   17.5556(5)
_cell_length_c                   14.1220(7)
_cell_measurement_reflns_used    3049
_cell_measurement_temperature    100
_cell_measurement_theta_max      72.4950
_cell_measurement_theta_min      3.5560
_cell_volume                     4352.4(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2417
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_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    -42.00  31.00   1.00    5.00    --  -44.40  19.00 -90.00   73
  2  \w     89.00 117.00   1.00    5.00    --   44.40 125.00-180.00   28
  3  \w   -157.00-130.00   1.00   20.00    --  -90.00-125.00 -60.00   27
  4  \w     39.00 122.00   1.00   20.00    --  100.00 -30.00  60.00   83
  5  \w     79.00 146.00   1.00   20.00    --  100.00  45.00 -30.00   67
  6  \w     53.00 107.00   1.00   20.00    --  100.00 -94.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0829892000
_diffrn_orient_matrix_UB_12      0.0275240000
_diffrn_orient_matrix_UB_13      0.0089766000
_diffrn_orient_matrix_UB_21      -0.0235928000
_diffrn_orient_matrix_UB_22      0.0540678000
_diffrn_orient_matrix_UB_23      0.0807748000
_diffrn_orient_matrix_UB_31      0.0158598000
_diffrn_orient_matrix_UB_32      -0.0633927000
_diffrn_orient_matrix_UB_33      0.0728487000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4706
_diffrn_reflns_point_group_measured_fraction_full 0.793
_diffrn_reflns_point_group_measured_fraction_max 0.792
_diffrn_reflns_theta_full        67.035
_diffrn_reflns_theta_max         67.035
_diffrn_reflns_theta_min         3.561
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.639
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.38103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.241
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0436
_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^)+(0.0894P)^2^+0.2138P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1245
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.517
_reflns_Friedel_fraction_full    0.566
_reflns_Friedel_fraction_max     0.566
_reflns_number_gt                2904
_reflns_number_total             3071
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02846_si_001.cif
_cod_data_source_block           zss_170313
_cod_depositor_comments          'Adding full bibliography for 1547734.cif.'
_cod_database_code               1547734
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.939
_shelx_estimated_absorpt_t_min   0.784
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C25(H25A,H25B), C28(H28A,H28B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C17(H17), C18(H18), C19(H19), C22(H22), C24(H24), C26(H26),
 C27(H27)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C29(H29A,H29B,
 H29C)
;
_shelx_res_checksum              14047
_shelx_hkl_checksum              50876
_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 2.851
_oxdiff_exptl_absorpt_empirical_full_min 0.492