A highly diastereoselective one-pot three-component 1,3-dipolar cycloaddition of cyclopropenes with azomethine ylides generated from 11H-indeno[1,2-b]-quinoxalin-11-ones
Filatov, A. S.; Knyazev, N. A.; Ryazantsev, M. N.; Suslonov, V. V.; Larina, A. G.; Molchanov, A. P.; Kostikov, R. R.; Boitsov, V. M.; Stepakov, A. V.; Organic Chemistry Frontiers 5 (2018) 595–; doi:10.1039/C7QO00888K

data_1553931
_publ_section_title
;
 A highly diastereoselective one-pot three-component 1,3-dipolar
 cycloaddition of cyclopropenes with azomethine ylides generated from
 11H-indeno[1,2-b]-quinoxalin-11-ones
;
_journal_issue                   4
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              595
_journal_paper_doi               10.1039/C7QO00888K
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C43 H29 N3'
_chemical_formula_sum            'C43 H29 N3'
_chemical_formula_weight         587.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-10-28
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2017-10-28 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.389(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7752(5)
_cell_length_b                   18.4617(8)
_cell_length_c                   18.0848(9)
_cell_measurement_reflns_used    6749
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.7260
_cell_measurement_theta_min      2.9370
_cell_volume                     3187.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   15.00   45.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000 -180.0000 30

  2 omega   12.00   43.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   57.0000   90.0000 31

  3 omega  -98.00  -37.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241 -178.0000 -150.0000 61

  4 omega  -89.00  -45.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  178.0000  -90.0000 44

  5 omega   -7.00   92.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -       23.3616   77.0000  120.0000 99

  6 omega   26.00   60.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000    0.0000 34

  7 omega   10.00   49.00   1.0000   16.2600
omega____ theta____ kappa____ phi______ frames
    -      -22.4241   38.0000    0.0000 39
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0090491000
_diffrn_orient_matrix_UB_12      0.0381197000
_diffrn_orient_matrix_UB_13      0.0004171000
_diffrn_orient_matrix_UB_21      0.0164786000
_diffrn_orient_matrix_UB_22      -0.0004235000
_diffrn_orient_matrix_UB_23      0.0401444000
_diffrn_orient_matrix_UB_31      0.0718992000
_diffrn_orient_matrix_UB_32      -0.0046859000
_diffrn_orient_matrix_UB_33      -0.0003748000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0287
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            21229
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.856
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0427
_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^)+(0.0359P)^2^+1.4052P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0926
_refine_ls_wR_factor_ref         0.0987
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6168
_reflns_number_total             7299
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00888k2.cif
_cod_data_source_block           step-65
_cod_database_code               1553931
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C43 H29 N3'
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.986
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Aromatic/amide H refined with riding coordinates:
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C42(H42), C43(H43),
 C44(H44), C45(H45), C46(H46), C52(H52), C53(H53), C54(H54), C55(H55), C56(H56),
  C62(H62), C63(H63), C64(H64), C65(H65), C66(H66), C1'(H1'), C2'(H2'),
 C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'), C12'(H12')
;
_shelx_res_checksum              50596
_shelx_hkl_checksum              68639
_olex2_submission_special_instructions 'No special instructions were received'