Bicyclic imidazoles for modular synthesis of chiral imidazolium salts.
Yoshida, Kazuhiro; Horiuchi, Shingo; Takeichi, Tomoko; Shida, Hiroaki; Imamoto, Tsuneo; Yanagisawa, Akira; Organic letters 12 (2010) 1764–1767; doi:10.1021/ol1003737

data_1502914
_publ_section_title
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 Bicyclic imidazoles for modular synthesis of chiral imidazolium salts.
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_journal_issue                   8
_journal_name_full               'Organic letters'
_journal_page_first              1764
_journal_page_last               1767
_journal_paper_doi               10.1021/ol1003737
_journal_volume                  12
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H29 B Cl F4 N5 Ni, C H2 Cl2'
_chemical_formula_sum            'C32 H31 B Cl3 F4 N5 Ni'
_chemical_formula_weight         737.49
_chemical_melting_point          460(2)
_chemical_name_common
'[(R,R)-2,6-Bis(5-phenyl-6,7-dihydro-5H-pyrrolo[1,2-c]imidazolium-2-yl)lutidine]chloronickel tetrafluoroborate'
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2702(7)
_cell_length_b                   15.5740(12)
_cell_length_c                   22.6712(17)
_cell_measurement_reflns_used    3781
_cell_measurement_temperature    173
_cell_measurement_theta_max      22.74
_cell_measurement_theta_min      2.37
_cell_volume                     3273.1(4)
_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-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0669
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18695
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.52
_diffrn_reflns_theta_min         1.59
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  0.9567
_exptl_absorpt_correction_T_min  0.7453
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.008
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.085
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7569
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0805P)^2^+0.4307P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1445
_reflns_number_gt                5784
_reflns_number_total             7569
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol1003737_si_003.cif
_cod_data_source_block           yoshida19_p212121
_cod_depositor_comments
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The following automatic conversions were performed:

'_chemical_melting_point' value '185-189 C' was changed to '460(2)' -
it was converted from degrees Celsius(C) to Kelvins(K), the average
value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Orthorhombic' changed to
'orthorhombic' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
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_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               1502914