Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C-H Bond Activation.
Chen, Zhan; Jin, Shengnan; Jiang, Wenyao; Zhu, Feimin; Chen, Yuqi; Zhao, Yingwei; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01303

data_4038629
_publ_section_title
;
 Multicomponent Synthesis of Iminocoumarins via Rhodium-Catalyzed C-H Bond
 Activation.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01303
_journal_year                    2020
_chemical_formula_moiety         'C28 H20 Br N O3 S'
_chemical_formula_sum            'C28 H20 Br N O3 S'
_chemical_formula_weight         530.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2019-08-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r1)
;
_cell_angle_alpha                104.269(6)
_cell_angle_beta                 101.676(5)
_cell_angle_gamma                98.093(6)
_cell_formula_units_Z            2
_cell_length_a                   9.2380(7)
_cell_length_b                   11.0371(9)
_cell_length_c                   12.9522(7)
_cell_measurement_reflns_used    2250
_cell_measurement_temperature    273
_cell_measurement_theta_max      26.8900
_cell_measurement_theta_min      3.8240
_cell_volume                     1227.84(16)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      273
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1213
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.9968
_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    -32.00  46.00   1.00    3.50    --  -16.28  57.00 -60.00   78
  2  \w     37.00  76.00   1.00    3.50    --   15.49  57.00-120.00   39
  3  \w     -1.00  81.00   1.00    3.50    --   15.49  57.00-150.00   82
  4  \w    -25.00  18.00   1.00    3.50    --  -16.28 -99.00   0.00   43
  5  \w    -48.00  42.00   1.00    3.50    --   15.49 -77.00  90.00   90
  6  \w     35.00  81.00   1.00    3.50    --   15.49 178.00  90.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0757766000
_diffrn_orient_matrix_UB_12      -0.0004778000
_diffrn_orient_matrix_UB_13      0.0033082000
_diffrn_orient_matrix_UB_21      -0.0242537000
_diffrn_orient_matrix_UB_22      -0.0202839000
_diffrn_orient_matrix_UB_23      -0.0582131000
_diffrn_orient_matrix_UB_31      -0.0086742000
_diffrn_orient_matrix_UB_32      -0.0645786000
_diffrn_orient_matrix_UB_33      0.0009247000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            10172
_diffrn_reflns_theta_full        24.9996
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.56
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47688
_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_density_diffrn    1.4347
_exptl_crystal_description       block
_exptl_crystal_F_000             539.9112
_refine_diff_density_max         0.3740
_refine_diff_density_min         -0.6185
_refine_diff_density_rms         0.1101
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             5.7166
_refine_ls_goodness_of_fit_ref   1.0518
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0518
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0468P)^2^+0.0773P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.1101
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3105
_reflns_number_total             4300
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo0c01303_si_001.cif
_cod_data_source_block           exp_5457
_cod_original_cell_volume        1227.83(16)
_cod_database_code               4038629
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C00M(H00M), C00J(H00J), C00G(H00G), C00Q(H00Q), C00T(H00T), C00P(H00P),
 C00L(H00L), C00H(H00H), C00K(H00K), C00W(H00W), C00V(H00V), C00R(H00R),
 C00I(H00I), C00S(H00S), C00X(H00X), C00U(H00U), C00N(H00N)
2.b Idealised Me refined as rotating group:
 C00Y(H00a,H00b,H00c)
;
_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 0.596