Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and Azomethine Ylides via [3 + 2]-Cycloaddition.
Filatov, Alexander S.; Knyazev, Nickolay A.; Molchanov, Alexander P.; Panikorovsky, Taras L.; Kostikov, Rafael R.; Larina, Anna G.; Boitsov, Vitali M.; Stepakov, Alexander V.; The Journal of organic chemistry 82 (2017) 959–975; doi:10.1021/acs.joc.6b02505

data_4032121
_publ_section_title
;
 Synthesis of Functionalized 3-Spiro[cyclopropa[a]pyrrolizine]- and
 3-Spiro[3-azabicyclo[3.1.0]hexane]oxindoles from Cyclopropenes and
 Azomethine Ylides via [3 + 2]-Cycloaddition.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              959
_journal_page_last               975
_journal_paper_doi               10.1021/acs.joc.6b02505
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C40 H34 N2 O'
_chemical_formula_sum            'C40 H34 N2 O'
_chemical_formula_weight         558.69
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-31
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.980(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5975(3)
_cell_length_b                   13.6912(3)
_cell_length_c                   20.7918(5)
_cell_measurement_reflns_used    7677
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.9230
_cell_measurement_theta_min      2.9820
_cell_volume                     2994.38(13)
_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, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16.2096
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -96.00  -35.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081 -178.0000  -30.0000 61

  2 omega  -95.00  -65.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081 -178.0000  150.0000 30

  3 omega  -48.00    1.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.4081  -57.0000 -180.0000 49

  4 omega  -46.00   29.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456  -57.0000  -60.0000 75

  5 omega   36.00   83.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456  178.0000  -90.0000 47

  6 omega    2.00   80.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456   57.0000 -180.0000 78

  7 omega    9.00   35.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456  -57.0000  -30.0000 26

  8 omega   11.00   61.00   1.0000   57.0000
omega____ theta____ kappa____ phi______ frames
    -       21.3456   38.0000  120.0000 50
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0417863000
_diffrn_orient_matrix_UB_12      0.0075722000
_diffrn_orient_matrix_UB_13      0.0237568000
_diffrn_orient_matrix_UB_21      0.0495596000
_diffrn_orient_matrix_UB_22      0.0233838000
_diffrn_orient_matrix_UB_23      0.0203297000
_diffrn_orient_matrix_UB_31      -0.0184584000
_diffrn_orient_matrix_UB_32      0.0455812000
_diffrn_orient_matrix_UB_33      -0.0143255000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            24764
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.721
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95828
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_description       prism
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         6871
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0401
_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^)+(0.0414P)^2^+1.3400P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5794
_reflns_number_total             6871
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02505_si_002.cif
_cod_data_source_block           step_52
_cod_depositor_comments
'Adding full bibliography for 4032118--4032121.cif.'
_cod_original_cell_volume        2994.39(13)
_cod_database_code               4032121
_chemical_oxdiff_formula         'C40 H34 N2 O'
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C5A(H5A)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C5(H5B,H5C), C4(H4A,H4B), C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1A6(H1A6), C1A2(H1A2), C4'(H4'), C5B2(H5B2), C66(H66), C1A5(H1A5), C13(H13),
 C1A4(H1A4), C1A3(H1A3), C5B3(H5B3), C5B5(H5B5), C16(H16), C5'(H5'), C5B6(H5B6),
  C7'(H7'), C62(H62), C65(H65), C12(H12), C5B4(H5B4), C63(H63), C64(H64),
 C14(H14), C6'(H6'), C15(H15)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'