Synthesis of Chiral Bicyclic Guanidinium Salts using Di(imidazole-1-yl)methanimine.
Turočkin, Aleksej; Honeker, Roman; Raven, William; Selig, Philipp; The Journal of organic chemistry 81 (2016) 4516–4529; doi:10.1021/acs.joc.6b00283

data_4036680
_publ_section_title
;
 Synthesis of Chiral Bicyclic Guanidinium Salts using
 Di(imidazole-1-yl)methanimine.
;
_journal_issue                   11
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4516
_journal_page_last               4529
_journal_paper_doi               10.1021/acs.joc.6b00283
_journal_volume                  81
_journal_year                    2016
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C33 H34 N3, Cl, 2(H2 O)'
_chemical_formula_sum            'C33 H38 Cl N3 O2'
_chemical_formula_weight         544.11
_chemical_melting_point          unk
_chemical_name_common            10
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 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                   7.1107(11)
_cell_length_b                   16.739(3)
_cell_length_c                   23.312(4)
_cell_measurement_temperature    100(2)
_cell_volume                     2774.7(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD Area Detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0666
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            15776
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.465
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.514
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 772 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.08(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     180
_refine_ls_number_reflns         2573
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0492
_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^)+(0.0357P)^2^+1.5817P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1062
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2124
_reflns_number_total             2573
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00283_si_001.cif
_cod_data_source_block           10
_cod_original_cell_volume        2774.7(7)
_cod_database_code               4036680
_shelx_estimated_absorpt_t_min   0.948
_shelx_estimated_absorpt_t_max   0.978
_shelxl_version_number           2013-2
_shelx_res_checksum              43830
_shelx_hkl_checksum              27400