A chiral analog of the bicyclic guanidine TBD: synthesis, structure and Brønsted base catalysis.
Goldberg, Mariano; Sartakov, Denis; Bats, Jan W.; Bolte, Michael; Göbel, Michael W; Beilstein journal of organic chemistry 12 (2016) 1870–1876; doi:10.3762/bjoc.12.176

data_4032044
_publ_section_title
;
 A chiral analog of the bicyclic guanidine TBD: synthesis, structure and
 Br\/onsted base catalysis.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              1870
_journal_page_last               1876
_journal_paper_doi               10.3762/bjoc.12.176
_journal_volume                  12
_journal_year                    2016
_chemical_formula_moiety         'C25 H18 Cl N O3'
_chemical_formula_sum            'C25 H18 Cl N O3'
_chemical_formula_weight         415.85
_space_group_crystal_system      orthorhombic
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_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'
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_cell_angle_beta                 90
_cell_angle_gamma                90
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_cell_length_b                   18.682(5)
_cell_length_c                   33.725(5)
_cell_measurement_reflns_used    4259
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.27
_cell_volume                     3957.9(14)
_computing_cell_refinement       'X-Area (Stoe & Cie, 2001)'
_computing_data_collection       'X-Area (Stoe & Cie, 2001)'
_computing_data_reduction        'X-Area (Stoe & Cie, 2001)'
_computing_molecular_graphics    'XP in SHELXTL-Plus (Sheldrick, 2008)'
_computing_publication_material  SHELXL
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_diffrn_measurement_device_type  'STOE IPDS II two-circle-diffractometer'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
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_diffrn_reflns_av_R_equivalents  0.4418
_diffrn_reflns_av_unetI/netI     0.4299
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
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_diffrn_reflns_point_group_measured_fraction_full 0.999
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_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
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_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.396
_exptl_crystal_description       needle
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_exptl_crystal_size_mid          0.020
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_refine_ls_abs_structure_details
; 
 Flack x determined using 420 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.4(4)
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         7819
_refine_ls_number_restraints     510
_refine_ls_restrained_S_all      0.953
_refine_ls_R_factor_all          0.2976
_refine_ls_R_factor_gt           0.1530
_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^)+(0.0122P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2038
_refine_ls_wR_factor_ref         0.2666
_reflns_Friedel_coverage         0.745
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.972
_reflns_number_gt                2557
_reflns_number_total             7819
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            1860-5397-12-176-S3.cif
_cod_data_source_block           g3
_cod_depositor_comments
'Adding full bibliography for 4032043--4032045.cif.'
_cod_database_code               4032044
_shelx_estimated_absorpt_t_min   0.939
_shelx_estimated_absorpt_t_max   0.996
_shelxl_version_number           2014/6
_shelx_res_checksum              2187
_shelx_hkl_checksum              21157