Intramolecular "Hydroiminiumation and -amidiniumation" of Alkenes: A Convenient, Flexible, and Scalable Route to Cyclic Iminium and Imidazolinium Salts
Rodolphe Jazzar; Jean-Baptiste Bourg; Rian D. Dewhurst; Bruno Donnadieu; Guy Bertrand; Journal of Organic Chemistry 72 (2007) 3492–3499; doi:10.1021/jo0703909

data_4022941
_publ_contact_author             'Prof G. Bertrand'
_publ_contact_author_address
;
University of California
Department of Chemistry
Riverside, CA 92521 USA
;
_publ_contact_author_email       'gbertrand@mail.ucr.edu '
_publ_contact_author_phone       909-787-2719
_publ_section_title
;
 Intramolecular "Hydroiminiumation and -amidiniumation"
 of Alkenes: A Convenient, Flexible, and Scalable Route to
 Cyclic Iminium and Imidazolinium Salts
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3492
_journal_page_last               3499
_journal_paper_doi               10.1021/jo0703909
_journal_volume                  72
_journal_year                    2007
_chemical_formula_sum            'C56 H82 Cl2 N4'
_chemical_formula_weight         882.16
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 108.2590(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.6299(18)
_cell_length_b                   19.1236(17)
_cell_length_c                   13.9795(12)
_cell_measurement_reflns_used    7345
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.34
_cell_volume                     5237.5(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    ORTEP3
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    Sir97
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            24727
_diffrn_reflns_theta_full        21.96
_diffrn_reflns_theta_max         21.96
_diffrn_reflns_theta_min         1.87
_exptl_absorpt_coefficient_mu    0.163
_exptl_absorpt_correction_T_max  0.9839
_exptl_absorpt_correction_T_min  0.9378
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.119
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'prism frag'
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.853
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.00048(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     576
_refine_ls_number_reflns         6333
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0594P)^2^+9.8768P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1462
_refine_ls_wR_factor_ref         0.1522
_reflns_number_gt                5407
_reflns_number_total             6333
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0703909si20070226_013125_1.cif
_cod_data_source_block           10a
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4022941