Synthesis of polysubstituted 3-aminoindenes via rhodium-catalysed [3 + 2] cascade annulations of benzimidates with alkenes
Wu, Binjie; Yang, Zi; Zhang, Hong; Wang, Lianhui; Cui, Xiuling; Chemical Communications  (2019) –; doi:10.1039/C9CC00567F

data_7123137
_publ_section_title
;
 Synthesis of polysubstituted 3-aminoindenes via rhodium-catalysed [3 + 2]
 cascade annulations of benzimidates with alkenes
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00567F
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc21f0h0
_audit_creation_date             2018-06-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-01-08 deposited with the CCDC.    2019-03-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8259(6)
_cell_length_b                   12.3491(8)
_cell_length_c                   13.8190(9)
_cell_measurement_reflns_used    2463
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6550
_cell_measurement_theta_min      3.5720
_cell_volume                     1676.81(18)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
  1 omega -102.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000  150.0000 93

  2 omega -105.00  -74.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 31

  3 omega   14.00   40.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   37.0000   60.0000 26

  4 omega   33.00   86.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734   57.0000  -90.0000 53

  5 omega   82.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  178.0000    0.0000 26

  6 omega   65.00   90.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -180.0000 25

  7 omega   39.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  150.0000 52

  8 omega   39.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000   90.0000 52

  9 omega  106.00  153.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 47

 10 omega   41.00   67.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -15.0000 -180.0000 26

 11 omega   39.00   71.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000 -120.0000 32

 12 omega   48.00   97.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000  -90.0000 49

 13 omega   58.00  103.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -94.0000   60.0000 45

 14 omega   26.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   30.0000 33

 15 omega   34.00   59.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 25

 16 omega  -30.00    1.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -77.0000   30.0000 31

 17 omega  -26.00    6.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       36.4734  -37.0000   30.0000 32

 18 omega   38.00   83.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -45.0000   30.0000 45

 19 omega   54.00   80.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -30.0000  -30.0000 26

 20 omega  126.00  152.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 26

 21 omega   79.00  120.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  -30.0000 41

 22 omega   39.00  134.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -180.0000 95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0374581000
_diffrn_orient_matrix_UB_12      -0.0963077000
_diffrn_orient_matrix_UB_13      0.0656843000
_diffrn_orient_matrix_UB_21      0.1520555000
_diffrn_orient_matrix_UB_22      0.0191758000
_diffrn_orient_matrix_UB_23      -0.0213449000
_diffrn_orient_matrix_UB_31      0.0090399000
_diffrn_orient_matrix_UB_32      0.0768377000
_diffrn_orient_matrix_UB_33      0.0875016000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6963
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.136
_diffrn_reflns_theta_min         4.803
_diffrn_source                   'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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    1.233
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.121
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1022 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       0.0049(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         3192
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0404
_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^)+(0.0418P)^2^+0.0830P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0944
_refine_ls_wR_factor_ref         0.1006
_reflns_Friedel_coverage         0.731
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                2802
_reflns_number_total             3192
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc00567f2.cif
_cod_data_source_block           201805260
_cod_original_cell_volume        1676.82(18)
_cod_database_code               7123137
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C15H15O3N3
_shelx_estimated_absorpt_t_max   0.917
_shelx_estimated_absorpt_t_min   0.902
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C13(H13), C14(H14),
 C15(H15), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22)
;
_olex2_submission_special_instructions 'No special instructions were received'