Metal-free aminoamidiniumation employing N-iodosuccinimide: facile syntheses of bicyclic imidazolidiniums and cyclic vicinal diamines
Jun Zhang; Gengtao Zhang; Weijie Wu; Xuejun Zhang; Min Shi; Chem.Commun. 50 (2014) 15052–; doi:10.1039/C4cc07082H

data_7116012
_publ_section_title
;
 Metal-free aminoamidiniumation employing N-iodosuccinimide: facile
 syntheses of bicyclic imidazolidiniums and cyclic vicinal diamines
;
_journal_name_full               Chem.Commun.
_journal_page_first              15052
_journal_paper_doi               10.1039/C4cc07082H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_sum            'C18 H19 I N2'
_chemical_formula_weight         390.25
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.6862(13)
_cell_length_b                   10.542(2)
_cell_length_c                   23.520(5)
_cell_measurement_reflns_used    3928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.50
_cell_measurement_theta_min      2.12
_cell_volume                     1657.8(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            8490
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.783
_diffrn_reflns_theta_min         1.732
_exptl_absorpt_coefficient_mu    1.927
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details
; 
 Flack x determined using 1095 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.003(13)
_refine_ls_extinction_coef       0.0027(4)
_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   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3086
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0243
_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^)+(0.0263P)^2^] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0519
_refine_ls_wR_factor_ref         0.0530
_reflns_Friedel_coverage         0.696
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.958
_reflns_number_gt                2834
_reflns_number_total             3086
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc07082h2.cif
_cod_data_source_block           a40411a
_cod_original_cell_volume        1657.9(6)
_cod_database_code               7116012
_shelx_estimated_absorpt_t_min   0.699
_shelx_estimated_absorpt_t_max   0.910
_shelxl_version_number           2013-2
_shelx_res_checksum              71930