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_4032118
_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         '2(C29 H26 N2 O3)'
_chemical_formula_sum            'C58 H52 N4 O6'
_chemical_formula_weight         901.03
_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                 123.702(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   18.7663(13)
_cell_length_b                   16.4529(6)
_cell_length_c                   9.1000(6)
_cell_measurement_reflns_used    4234
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.1202
_cell_measurement_theta_min      2.7851
_cell_volume                     2337.5(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
;
_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 0.989
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -97.00  -62.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  178.0000  -60.0000 35

  2 omega  -23.00   11.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -20.5643  -99.0000  -60.0000 34

  3 omega    0.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5018   57.0000 -150.0000 87

  4 omega   37.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5018   57.0000   60.0000 48

  5 omega    6.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       21.5018   57.0000  120.0000 64
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0417554000
_diffrn_orient_matrix_UB_12      0.0066631000
_diffrn_orient_matrix_UB_13      0.0193271000
_diffrn_orient_matrix_UB_21      -0.0153675000
_diffrn_orient_matrix_UB_22      -0.0072506000
_diffrn_orient_matrix_UB_23      -0.0897113000
_diffrn_orient_matrix_UB_31      -0.0092304000
_diffrn_orient_matrix_UB_32      0.0419618000
_diffrn_orient_matrix_UB_33      -0.0185699000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12176
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.791
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'translucent colorless'
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         5308
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0746P)^2^+0.8797P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1377
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4340
_reflns_number_total             5308
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02505_si_001.cif
_cod_data_source_block           step-51
_cod_depositor_comments
'Adding full bibliography for 4032118--4032121.cif.'
_cod_original_cell_volume        2337.5(3)
_cod_database_code               4032118
_chemical_oxdiff_formula         'C55 O9 H22 N4'
_reflns_odcompleteness_completeness 98.63
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C5A(H30)
2.b Secondary CH2 refined with riding coordinates:
 C3(H23A,H23B), C4(H24A,H24B), C5(H33A,H33B)
2.c Aromatic/amide H refined with riding coordinates:
 N1'(H1), C5B2(H6B1), C7'(H10), C1A5(H5A1), C5B6(H10B), C1A6(H6A1), C5B5(H9B1),
  C4'(H19), C5B4(H8B1), C1A3(H3A1), C1A2(H2A1), C6'(H26), C5B3(H7B1), C5'(H29),
 C1A4(H4A1)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'