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_4032043
_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_absolute_configuration syn
_chemical_formula_moiety         'C19 H22 N3, C7 H5 O2, 0.5(C4 H8 O2)'
_chemical_formula_sum            'C28 H31 N3 O3'
_chemical_formula_weight         457.56
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 101.0070(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.2019(12)
_cell_length_b                   9.6219(8)
_cell_length_c                   17.1451(14)
_cell_measurement_reflns_used    6112
_cell_measurement_temperature    185(2)
_cell_measurement_theta_max      23
_cell_measurement_theta_min      3
_cell_volume                     2461.7(3)
_computing_cell_refinement       'SAINT (Siemens, 1995)'
_computing_data_collection       'SMART (Siemens, 1995)'
_computing_data_reduction        'SAINT (Siemens, 1995)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      185(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  Siemens_SMART_1K_CCD
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1274
_diffrn_reflns_av_sigmaI/netI    0.1237
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25966
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         1.64
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_time  1200
_diffrn_standards_number         213
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2000)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.235
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     626
_refine_ls_number_reflns         5087
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.132
_refine_ls_R_factor_all          0.1706
_refine_ls_R_factor_gt           0.0943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.024P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0972
_refine_ls_wR_factor_ref         0.1135
_reflns_number_gt                2948
_reflns_number_total             5087
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            1860-5397-12-176-S2.cif
_cod_data_source_block           goldberg1
_cod_depositor_comments
'Adding full bibliography for 4032043--4032045.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4032043