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_1553929
_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 H31 N3 O, (C2 H5 O H)0.675'
_chemical_formula_sum            'C40.35 H35.05 N3 O1.67'
_chemical_formula_weight         588.76
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-06-18
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-06-17 deposited with the CCDC.
2017-11-01 downloaded from the CCDC.
;
_cell_angle_alpha                73.859(4)
_cell_angle_beta                 78.251(3)
_cell_angle_gamma                71.617(4)
_cell_formula_units_Z            2
_cell_length_a                   9.0006(3)
_cell_length_b                   13.4106(7)
_cell_length_c                   13.9272(4)
_cell_measurement_reflns_used    4875
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5910
_cell_measurement_theta_min      3.3210
_cell_volume                     1519.94(11)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3829
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -45.00   35.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037   38.0000  120.0000 80

  2 omega -116.00  -44.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037  178.0000   60.0000 72

  3 omega -114.00  -12.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -      -40.5037  -57.0000  -30.0000 102

  4 omega  -38.00   74.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5037  -77.0000 -120.0000 112

  5 omega  104.00  130.00   1.0000    7.5000
omega____ theta____ kappa____ phi______ frames
    -       40.5037  178.0000 -150.0000 26

  6 omega   45.00   76.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000 -180.0000 31

  7 omega   50.00  106.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  150.0000 56

  8 omega   29.00  104.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000 -120.0000 75

  9 omega  105.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000   45.0000 -150.0000 70

 10 omega   87.00  132.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000  -60.0000 45

 11 omega   86.00  112.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  -30.0000 26

 12 omega   43.00   87.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   60.0000 44

 13 omega   37.00  109.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000   60.0000 72

 14 omega   38.00   94.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 56

 15 omega   39.00   74.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 35

 16 omega   45.00  114.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000 -112.0000  120.0000 69

 17 omega   44.00  137.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -61.0000 -120.0000 93

 18 omega   31.00  162.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -15.0000 -150.0000 131
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.1291673000
_diffrn_orient_matrix_UB_12      0.0235851000
_diffrn_orient_matrix_UB_13      0.0407168000
_diffrn_orient_matrix_UB_21      -0.0912499000
_diffrn_orient_matrix_UB_22      0.1205968000
_diffrn_orient_matrix_UB_23      -0.0183470000
_diffrn_orient_matrix_UB_31      -0.0897564000
_diffrn_orient_matrix_UB_32      -0.0193246000
_diffrn_orient_matrix_UB_33      0.1071645000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10039
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.986
_diffrn_reflns_theta_min         3.331
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.616
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85994
_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            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       prism
_exptl_crystal_F_000             623
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     432
_refine_ls_number_reflns         5735
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0600
_refine_ls_R_factor_gt           0.0478
_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^)+(0.0716P)^2^+0.4434P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1249
_refine_ls_wR_factor_ref         0.1337
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4772
_reflns_number_total             5735
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00888k2.cif
_cod_data_source_block           step-63
_cod_original_cell_volume        1519.94(12)
_cod_database_code               1553929
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C39 N3 h29'
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.33
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H3-N3
 0.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2S) = Uanis(C3S)
Uanis(O1) = Uanis(O1A)
4. Others
 Sof(H1SC)=Sof(H1SD)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(H3SC)=0.34*FVAR(2)
 Sof(H1SA)=Sof(H1SB)=Sof(C2S)=Sof(H2SA)=Sof(H2SB)=Sof(H2SC)=0.66*FVAR(2)
 Sof(O1S)=Sof(H1S)=Sof(C1S)=FVAR(1)
 Sof(H11C)=Sof(H11D)=Sof(O1)=Sof(H1)=1-FVAR(2)
 Sof(O1A)=Sof(H1A)=Sof(H11A)=Sof(H11B)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6)
5.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C11(H11A,H11B), C11(H11C,H11D), C1S(H1SA,H1SB), C1S(H1SC,H1SD)
5.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C6'(H6'), C15(H15), C9'(H9'), C30(H30), C24(H24),
 C7'(H7'), C26(H26), C20(H20), C8'(H8'), C16(H16), C1'(H1'), C17(H17), C4'(H4'),
  C3'(H3'), C21(H21), C27(H27), C29(H29), C2'(H2'), C22(H22), C28(H28), C23(H23)
5.d Idealised Me refined as rotating group:
 C2S(H2SA,H2SB,H2SC), C3S(H3SA,H3SB,H3SC)
5.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1S(H1S), O1(H1)
;
_olex2_date_sample_data_collection 1488218796.35
_olex2_submission_special_instructions 'No special instructions were received'