Regio- and Stereoselective Synthesis of Spiropyrrolizidines and Piperazines through Azomethine Ylide Cycloaddition Reaction.
Haddad, Saoussen; Boudriga, Sarra; Porzio, François; Soldera, Armand; Askri, Moheddine; Knorr, Michael; Rousselin, Yoann; Kubicki, Marek M.; Golz, Christopher; Strohmann, Carsten; The Journal of organic chemistry 80 (2015) 9064–9075; doi:10.1021/acs.joc.5b01399

data_4036285
_publ_section_title
;
 Regio- and Stereoselective Synthesis of Spiropyrrolizidines and
 Piperazines through Azomethine Ylide Cycloaddition Reaction.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9064
_journal_page_last               9075
_journal_paper_doi               10.1021/acs.joc.5b01399
_journal_volume                  80
_journal_year                    2015
_chemical_formula_moiety         'C32 H26 N2 O2'
_chemical_formula_sum            'C32 H26 N2 O2'
_chemical_formula_weight         470.55
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-01-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.19 svn.r3143 for OlexSys, GUI svn.r4992)
;
_cell_angle_alpha                109.553(8)
_cell_angle_beta                 100.777(7)
_cell_angle_gamma                102.741(7)
_cell_formula_units_Z            2
_cell_length_a                   8.8650(7)
_cell_length_b                   10.6628(9)
_cell_length_c                   14.2130(11)
_cell_measurement_reflns_used    2999
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.6780
_cell_measurement_theta_min      2.6930
_cell_volume                     1184.09(19)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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      173.15
_diffrn_detector_area_resol_mean 16.0560
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
  1 omega   -3.00   86.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472   57.0000 -150.0000 89

  2 omega   -8.00   90.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472   38.0000  -30.0000 98

  3 omega  -53.00   39.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472  -38.0000 -150.0000 92

  4 omega   26.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472   38.0000   30.0000 58

  5 omega  -24.00   59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472  -99.0000    0.0000 83

  6 omega  -21.00   24.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -99.0000    0.0000 45

  7 omega  -39.00   28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847   57.0000   90.0000 67

  8 omega  -91.00    6.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -38.0000   60.0000 97

  9 omega  -81.00   -4.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  134.0000   86.0441 77
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0026794000
_diffrn_orient_matrix_UB_12      -0.0567923000
_diffrn_orient_matrix_UB_13      0.0149584000
_diffrn_orient_matrix_UB_21      -0.0594444000
_diffrn_orient_matrix_UB_22      -0.0464140000
_diffrn_orient_matrix_UB_23      -0.0471912000
_diffrn_orient_matrix_UB_31      0.0614605000
_diffrn_orient_matrix_UB_32      -0.0108529000
_diffrn_orient_matrix_UB_33      -0.0244837000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15966
_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         25.997
_diffrn_reflns_theta_min         2.456
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.99219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4640
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0742
_refine_ls_R_factor_gt           0.0472
_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^)+(0.0391P)^2^+0.2549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0932
_refine_ls_wR_factor_ref         0.1044
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3346
_reflns_number_total             4640
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01399_si_002.cif
_cod_data_source_block           2890_compound_8a
_cod_original_cell_volume        1184.10(18)
_cod_database_code               4036285
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C32 H26 N2 O2'
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.976
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.00
_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), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C19(H19A,H19B),
 C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C13(H13), C14(H14), C15(H15), C24(H24), C25(H25),
 C26(H26), C29(H29), C30(H30), C31(H31)
;
_shelx_res_checksum              93009
_shelx_hkl_checksum              59857
_olex2_submission_special_instructions 'No special instructions were received'