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_4036282
_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         'C29 H24 F N3 O3'
_chemical_formula_sum            'C29 H24 F N3 O3'
_chemical_formula_weight         481.51
_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   mixed
_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                79.606(3)
_cell_angle_beta                 68.137(3)
_cell_angle_gamma                67.559(3)
_cell_formula_units_Z            4
_cell_length_a                   13.0271(5)
_cell_length_b                   13.1056(4)
_cell_length_c                   15.6355(5)
_cell_measurement_reflns_used    15570
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      28.8130
_cell_measurement_theta_min      2.5840
_cell_volume                     2287.54(15)
_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 0.993
_diffrn_measurement_details
;
  1 omega   -8.00   81.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909   77.0000 -180.0000 89

  2 omega  -22.00   59.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909  -99.0000   30.0000 81

  3 omega   -6.00   80.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909   77.0000  -30.0000 86

  4 omega  -52.00   20.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909  -57.0000  -60.0000 72

  5 omega    6.00   86.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909   57.0000   90.0000 80

  6 omega  -25.00   59.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909  -99.0000  150.0000 84

  7 omega    9.00   78.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909 -130.0000  -88.8246 69

  8 omega  -26.00   47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847   57.0000 -150.0000 73

  9 omega  -85.00    1.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -38.0000 -150.0000 86

 10 omega  -53.00   47.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909  -77.0000 -150.0000 100

 11 omega  -13.00   87.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909   77.0000  -60.0000 100

 12 omega  -52.00   38.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       16.9909  -57.0000   60.0000 90

 13 omega  -39.00   51.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847   57.0000  -60.0000 90

 14 omega  -87.00  -17.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -57.0000   60.0000 70

 15 omega  -25.00   24.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -99.0000   30.0000 49
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0546127000
_diffrn_orient_matrix_UB_12      0.0080783000
_diffrn_orient_matrix_UB_13      -0.0242054000
_diffrn_orient_matrix_UB_21      -0.0195399000
_diffrn_orient_matrix_UB_22      0.0245191000
_diffrn_orient_matrix_UB_23      -0.0380376000
_diffrn_orient_matrix_UB_31      -0.0232647000
_diffrn_orient_matrix_UB_32      0.0526233000
_diffrn_orient_matrix_UB_33      0.0190077000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            56795
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         2.623
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98399
_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    1.398
_exptl_crystal_description       block
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.299
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.042
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     657
_refine_ls_number_reflns         9928
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0403
_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^)+(0.0373P)^2^+1.0297P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0879
_refine_ls_wR_factor_ref         0.0968
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7798
_reflns_number_total             9928
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01399_si_002.cif
_cod_data_source_block           2888_compound_4e
_cod_original_cell_volume        2287.53(16)
_cod_database_code               4036282
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C29 H24 Br1 N3 O3'
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.971
_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. Restrained distances
 N7-H7A = N2-H2
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C30(H30), C34(H34), C1(H1), C5(H5)
3.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C44(H44A,H44B), C2(H2A,H2B),
 C3(H3A,H3B), C4(H4A,H4B), C13(H13A,H13B)
3.c Aromatic/amide H refined with riding coordinates:
 C36(H36), C37(H37), C39(H39), C40(H40), C46(H46), C47(H47), C48(H48),
 C49(H49), C50(H50), C53(H53), C54(H54), C55(H55), C56(H56), C7(H7), C8(H8),
 C10(H10), C11(H11), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24),
  C25(H25), C26(H26), C27(H27)
;
_shelx_res_checksum              55039
_shelx_hkl_checksum              36716
_olex2_submission_special_instructions 'No special instructions were received'