Cobalt-catalyzed highly diastereoselective [3 + 2] carboannulation reactions: facile access to substituted indane derivatives
Dey, Arnab; Singh, Anurag; Volla, Chandra M. R.; Chemical Communications  (2022) –; doi:10.1039/D1CC05245D

data_7129514
_publ_section_title
;
 Cobalt-catalyzed highly diastereoselective [3 + 2] carboannulation
 reactions: facile access to substituted indane derivatives
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC05245D
_journal_year                    2022
_chemical_formula_moiety         'C25 H21 N3 O3'
_chemical_formula_sum            'C25 H21 N3 O3'
_chemical_formula_weight         411.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-14
_audit_creation_method
;
Olex2 1.2-ac3
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2020-01-31 deposited with the CCDC.	2021-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.839(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.931(3)
_cell_length_b                   10.1424(14)
_cell_length_c                   12.3571(16)
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    150
_cell_measurement_theta_max      30.5730
_cell_measurement_theta_min      2.3730
_cell_volume                     1992.2(5)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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    -59.00  49.00   0.50    8.00    --  -20.00  72.00  36.00  216
  2  \w    -68.50   0.00   0.50    8.00    --  -20.00 -72.00-180.00  137
  3  \w    -14.50  45.50   0.50    8.00    --  -20.00  72.00 108.00  120
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0403119000
_diffrn_orient_matrix_UB_12      -0.0246206000
_diffrn_orient_matrix_UB_13      -0.0175959000
_diffrn_orient_matrix_UB_21      0.0160580000
_diffrn_orient_matrix_UB_22      -0.0653208000
_diffrn_orient_matrix_UB_23      0.0039912000
_diffrn_orient_matrix_UB_31      -0.0109953000
_diffrn_orient_matrix_UB_32      -0.0032214000
_diffrn_orient_matrix_UB_33      0.0544881000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1137
_diffrn_reflns_av_unetI/netI     0.1454
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8562
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.382
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
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    1.372
_exptl_crystal_description       needle
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.051
_refine_diff_density_max         0.314
_refine_diff_density_min         -0.325
_refine_diff_density_rms         0.076
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3482
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.990
_refine_ls_R_factor_all          0.1890
_refine_ls_R_factor_gt           0.0887
_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^)+(0.1453P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2131
_refine_ls_wR_factor_ref         0.3144
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1488
_reflns_number_total             3482
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc05245d2.cif
_cod_data_source_block           cmrv-ad-788_mo
_cod_database_code               7129514
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.984
_reflns_odcompleteness_completeness 88.17
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.14
_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:
 C8(H8), C9(H9), C20(H20), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C21(H21), C3(H3), C1(H1), C13(H13), C14(H14), C15(H15),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C16(H16A,H16B,H16C)
;
_shelx_res_checksum              74712
_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 6.004
_oxdiff_exptl_absorpt_empirical_full_min 0.548