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_4036283
_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 Cl N3 O3'
_chemical_formula_sum            'C29 H24 Cl N3 O3'
_chemical_formula_weight         497.96
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.5387(5)
_cell_length_b                   12.5979(6)
_cell_length_c                   19.8057(11)
_cell_measurement_reflns_used    5045
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      27.8060
_cell_measurement_theta_min      2.6640
_cell_volume                     2380.0(2)
_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 0.995
_diffrn_measurement_details
;
  1 omega   -7.00   85.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472   77.0000   90.0000 92

  2 omega  -47.00   46.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472  -77.0000  -30.0000 93

  3 omega   46.00   76.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472 -179.0000  -60.0000 30

  4 omega   37.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472 -179.0000  150.0000 54

  5 omega   -4.00   78.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       17.1472   57.0000 -120.0000 82

  6 omega  -17.00   14.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847  -99.0000  -30.0000 31

  7 omega  -66.00  -38.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -18.0847 -179.0000   30.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0062954000
_diffrn_orient_matrix_UB_12      -0.0501295000
_diffrn_orient_matrix_UB_13      -0.0159917000
_diffrn_orient_matrix_UB_21      -0.0258061000
_diffrn_orient_matrix_UB_22      0.0251812000
_diffrn_orient_matrix_UB_23      -0.0295224000
_diffrn_orient_matrix_UB_31      0.0694819000
_diffrn_orient_matrix_UB_32      0.0048035000
_diffrn_orient_matrix_UB_33      -0.0124217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            19681
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_min         2.370
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90667
_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    1.390
_exptl_crystal_description       block
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1666 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.38(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0391
_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^)+(0.0322P)^2^+0.5399P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.753
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                4350
_reflns_number_total             5130
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01399_si_002.cif
_cod_data_source_block           2889-compound_5d
_cod_database_code               4036283
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C29 H24 Cl1 N3 O3'
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.925
_reflns_odcompleteness_completeness 99.82
_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), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C20(H20), C21(H21), C25(H25), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              63854
_shelx_hkl_checksum              7125
_olex2_submission_special_instructions 'No special instructions were received'