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_1553930
_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         'C39 H29 N3 O2'
_chemical_formula_sum            'C39 H29 N3 O2'
_chemical_formula_weight         571.65
_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   mixed
_atom_sites_solution_primary     iterative
_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                 96.753(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.8591(3)
_cell_length_b                   17.6789(6)
_cell_length_c                   16.9614(6)
_cell_measurement_reflns_used    3806
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3440
_cell_measurement_theta_min      2.7650
_cell_volume                     2935.83(17)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -75.00   -1.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -22.4241  -57.0000   90.0000 74

  2 omega  -16.00   60.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -99.0000   60.0000 76

  3 omega    0.00   48.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616  -38.0000  -90.0000 48

  4 omega   34.00   84.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -       23.3616 -178.0000  -60.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0480568000
_diffrn_orient_matrix_UB_12      0.0162611000
_diffrn_orient_matrix_UB_13      0.0230546000
_diffrn_orient_matrix_UB_21      -0.0370871000
_diffrn_orient_matrix_UB_22      0.0147833000
_diffrn_orient_matrix_UB_23      -0.0349729000
_diffrn_orient_matrix_UB_31      -0.0395605000
_diffrn_orient_matrix_UB_32      -0.0335662000
_diffrn_orient_matrix_UB_33      -0.0042432000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14357
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.777
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98541
_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    1.293
_exptl_crystal_description       prism
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6716
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0520
_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^)+(0.0467P)^2^+1.5519P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1152
_refine_ls_wR_factor_ref         0.1249
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5168
_reflns_number_total             6716
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00888k2.cif
_cod_data_source_block           step-66
_cod_database_code               1553930
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C39 H29 N3 O2'
_reflns_odcompleteness_completeness 99.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     28.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C44A) = Uanis(C44)
3. Others
 Sof(C42A)=Sof(H42A)=Sof(C43A)=Sof(H43A)=Sof(C44A)=Sof(H44A)=Sof(C45A)=
 Sof(H45A)=Sof(C46A)=Sof(H46A)=1-FVAR(1)
 Sof(C42)=Sof(H42)=Sof(C43)=Sof(H43)=Sof(C44)=Sof(H44)=Sof(C45)=Sof(H45)=
 Sof(C46)=Sof(H46)=FVAR(1)
4.a Riding coordinates:
 N3(H3)
4.b Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
4.c 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),
  C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C9'(H9'), C10'(H10'), C11'(H11'),
 C12'(H12'), C42A(H42A), C43A(H43A), C44A(H44A), C45A(H45A), C46A(H46A)
4.d Idealised Me refined as rotating group:
 C62(H62A,H62B,H62C)
;
_shelx_res_checksum              55575
_shelx_hkl_checksum              40198
_olex2_submission_special_instructions 'No special instructions were received'