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_4032120
_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         'C38 H33 N2 O'
_chemical_formula_sum            'C38 H33 N2 O'
_chemical_formula_weight         533.66
_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   mixed
_atom_sites_solution_primary     iterative
_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                 113.80(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.1100(3)
_cell_length_b                   21.2864(10)
_cell_length_c                   17.7101(3)
_cell_measurement_reflns_used    6989
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.4044
_cell_measurement_theta_min      2.6873
_cell_volume                     2797.3(11)
_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
;
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 0.984
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
  1 omega  -98.00  -67.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -      -25.4031 -178.0000  -90.0000 31

  2 omega   32.00   68.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   60.0000 36

  3 omega  -25.00   67.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000  -60.0000 92

  4 omega   -4.00   22.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968 -123.0000 -169.0000 26

  5 omega   33.00   80.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968 -123.0000 -169.0000 47

  6 omega   13.00   95.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   57.0000   90.0000 82

  7 omega   -9.00   17.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968  -99.0000   60.0000 26

  8 omega   16.00   48.00   1.0000  100.0000
omega____ theta____ kappa____ phi______ frames
    -       26.4968   38.0000    0.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0375974000
_diffrn_orient_matrix_UB_12      -0.0210205000
_diffrn_orient_matrix_UB_13      -0.0036251000
_diffrn_orient_matrix_UB_21      0.0193251000
_diffrn_orient_matrix_UB_22      -0.0256313000
_diffrn_orient_matrix_UB_23      -0.0080732000
_diffrn_orient_matrix_UB_31      0.0909645000
_diffrn_orient_matrix_UB_32      -0.0032043000
_diffrn_orient_matrix_UB_33      0.0871979000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20184
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.692
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95841
_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    1.267
_exptl_crystal_description       prism
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.319
_refine_diff_density_min         -0.763
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6286
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0426
_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^)+(0.0406P)^2^+1.6826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1056
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5445
_reflns_number_total             6286
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02505_si_003.cif
_cod_data_source_block           step-53
_cod_depositor_comments
'Adding full bibliography for 4032118--4032121.cif.'
_cod_original_cell_volume        2797(12)
_cod_database_code               4032120
_chemical_oxdiff_formula         'C38 H33 N2 O'
_reflns_odcompleteness_completeness 97.01
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.01
_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 Riding coordinates:
 N2(H2)
2.b Ternary CH refined with riding coordinates:
 C1(H1)
2.c Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B)
2.d Aromatic/amide H refined with riding coordinates:
 C12(H12), C16(H16), C4'(H4'), C4A6(H4A6), C4A2(H4A2), C1A2(H1A2), C7'(H7'),
 C6'(H6'), C4A5(H4A5), C15(H15), C4A3(H4A3), C4A4(H4A4), C1A6(H1A6), C5'(H5'),
 C1A3(H1A3), C66(H66), C14(H14), C13(H13), C1A4(H1A4), C62(H62), C65(H65),
 C1A5(H1A5), C64(H64), C63(H63)
2.e Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'