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_4036284
_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      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
_audit_creation_date             2013-01-11
_audit_creation_method
;
  Olex2 1.2
  (compiled 2012.12.05 svn.r2549, GUI svn.r4385)
;
_audit_update_record
;
2013-01-11 # Formatted by publCIF
;
_cell_angle_alpha                95.3790(10)
_cell_angle_beta                 95.980(2)
_cell_angle_gamma                92.8110(10)
_cell_formula_units_Z            2
_cell_length_a                   8.6262(2)
_cell_length_b                   9.9045(3)
_cell_length_c                   14.3555(5)
_cell_measurement_reflns_used    9911
_cell_measurement_temperature    115
_cell_measurement_theta_max      27.6077
_cell_measurement_theta_min      2.3782
_cell_volume                     1212.32(6)
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_collection       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution
'SHELXS-97, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122'
_diffrn_ambient_temperature      115.0
_diffrn_detector                 'CCD Plate'
_diffrn_detector_area_resol_mean 9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       '\k-geometry diffractometer'
_diffrn_measurement_device_type  'Nonius Kappa Apex II'
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_radiation_collimation    '0.6 mm'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a~1~'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0229
_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       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31894
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.613
_diffrn_reflns_theta_min         1.433
_diffrn_source                   'X-ray tube'
_diffrn_source_target            Mo
_diffrn_source_type              'Siemens KFF Mo 2K-180'
_exptl_absorpt_coefficient_mu    0.195
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_correction_T_min  0.69
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_description       cube
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     325
_refine_ls_number_reflns         5615
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0358
_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^)+(0.0395P)^2^+0.6674P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0854
_refine_ls_wR_factor_ref         0.0919
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4730
_reflns_number_total             5615
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01399_si_002.cif
_cod_data_source_block           13mksp41_compound_6d
_cod_database_code               4036284
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  H2 of N2, H8 of C8, H9 of C9, H10 of C10, H11 of C11, H17 of C17, H16 of
  C16, H14 of C14, H28 of C28, H27 of C27, H26 of C26, H20 of C20, H19 of C19,
  H1 of C1, {H4A,H4B} of C4, {H3A,H3B} of C3, H25 of C25, {H2A,H2B} of C2,
  {H21A,H21B} of C21, H24 of C24
2.a Ternary CH refined with riding coordinates:
 C14(H14), C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C2(H2A,H2B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C16(H16), C28(H28), C27(H27), C26(H26), C20(H20), C19(H19),
 C25(H25), C24(H24), N2(H2), C8(H8), C9(H9), C10(H10), C11(H11)
;
_shelx_estimated_absorpt_t_max   0.953
_shelx_estimated_absorpt_t_min   0.953
_shelx_hkl_checksum              96995
_shelx_res_checksum              23850
_shelxl_version_number           2012-9