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_4036679
_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         'C20 H24 N3, Cl, H2 O'
_chemical_formula_sum            'C20 H26 Cl N3 O'
_chemical_formula_weight         359.89
_chemical_melting_point          unk
_chemical_name_common            8
_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   difmap
_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                   10.807(2)
_cell_length_b                   11.284(2)
_cell_length_c                   15.094(3)
_cell_measurement_temperature    100(2)
_cell_volume                     1840.7(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0446
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22832
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.793
_diffrn_reflns_theta_min         2.318
_diffrn_source                   'Incoatec microsource'
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.6269
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1824 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4781
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0365
_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^)+(0.0500P)^2^+0.2288P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0882
_refine_ls_wR_factor_ref         0.0915
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                4438
_reflns_number_total             4781
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00283_si_001.cif
_cod_data_source_block           8
_cod_original_cell_volume        1840.6(6)
_cod_database_code               4036679
_shelx_estimated_absorpt_t_min   0.929
_shelx_estimated_absorpt_t_max   0.949
_shelxl_version_number           2013-2
_shelx_res_checksum              26525
_shelx_hkl_checksum              44181