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_4032119
_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         'C34 H32 N2 O'
_chemical_formula_sum            'C34 H32 N2 O'
_chemical_formula_weight         484.61
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 95.1831(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.15402(15)
_cell_length_b                   17.9078(3)
_cell_length_c                   12.87201(20)
_cell_measurement_reflns_used    7246
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.5430
_cell_measurement_theta_min      4.2160
_cell_volume                     2560.59(7)
_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, 2008)'
_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 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega  -55.00   24.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   77.0000  -30.0000 79

  2 omega  -31.00   29.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000  120.0000 60

  3 omega  -43.00   35.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -120.0000 78

  4 omega  -42.00   -9.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787   38.0000 -150.0000 33

  5 omega   39.00   78.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  150.0000 39

  6 omega   38.00   85.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   30.0000 47

  7 omega   35.00   67.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000   90.0000 32

  8 omega   49.00   91.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  120.0000 42

  9 omega   45.00   90.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -30.0000  -90.0000 45

 10 omega   27.00   83.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -180.0000 56

 11 omega   95.00  176.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000    0.0000 -180.0000 81

 12 omega   43.00   85.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000  -30.0000 42

 13 omega  142.00  167.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  120.0000 25

 14 omega  129.00  160.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  112.0000  -30.0000 31

 15 omega   30.00   96.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -95.0000  -90.0000 66

 16 omega   54.00   82.00   1.0000    9.0000
omega____ theta____ kappa____ phi______ frames
    -      113.0000  -45.0000    0.0000 28

 17 omega  -75.00  -38.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -57.0000  -30.0000 37

 18 omega  -89.00  -10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.3787  -77.0000   60.0000 79

 19 omega   69.00  125.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       40.3787  178.0000  -90.0000 56
;
_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      0.0714201000
_diffrn_orient_matrix_UB_12      0.0591998000
_diffrn_orient_matrix_UB_13      0.0667373000
_diffrn_orient_matrix_UB_21      0.1013729000
_diffrn_orient_matrix_UB_22      -0.0036018000
_diffrn_orient_matrix_UB_23      -0.0735399000
_diffrn_orient_matrix_UB_31      -0.0620681000
_diffrn_orient_matrix_UB_32      0.0622994000
_diffrn_orient_matrix_UB_33      -0.0677334000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13152
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.495
_diffrn_reflns_theta_min         4.241
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.582
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86037
_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            'translucent colorless'
_exptl_crystal_density_diffrn    1.257
_exptl_crystal_description       prism
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     336
_refine_ls_number_reflns         5065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0483P)^2^+0.9603P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1028
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4532
_reflns_number_total             5065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b02505_si_004.cif
_cod_data_source_block           103-427-5627_step-60
_cod_depositor_comments
'Adding full bibliography for 4032118--4032121.cif.'
_cod_original_cell_volume        2560.60(6)
_cod_database_code               4032119
_chemical_oxdiff_formula         'C34 H32 N2 O'
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C6A(H6A), C2'(H2'), C1(H1A)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B), C6(H6B,H6C)
2.c Aromatic/amide H refined with riding coordinates:
 C24(H24), C19(H19), C4'(H4'), C6'(H6'), C21(H21), C5'(H5'), C23(H23),
 C12(H12), C22(H22), C18(H18), C11(H11), C15(H15), C9(H9), C25(H25), C13(H13),
 C17(H17), C7'(H7'), C16(H16), C10(H10)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'