Synthesis and Applications of the C2-Symmetrical Diamine, 2,7-diazabicyclo[4.4.1]undecane.
Higgins, Tyler; Winkler, Jeffrey D.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00829

data_4038356
_publ_section_title
;
 Synthesis and Applications of the C2-Symmetrical Diamine,
 2,7-diazabicyclo[4.4.1]undecane.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00829
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C14 H26 Cl2 N2 Pd, C H Cl3'
_chemical_formula_sum            'C15 H27 Cl5 N2 Pd'
_chemical_formula_weight         519.03
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.2212(2)
_cell_length_b                   11.8966(2)
_cell_length_c                   14.6501(2)
_cell_measurement_reflns_used    9890
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.505
_cell_measurement_theta_min      2.857
_cell_volume                     1955.70(5)
_computing_data_collection       'Bruker APEX2 v2014.11-0'
_computing_data_reduction        'SAINT V8.38A (2016)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CCD area detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_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       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25574
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.530
_diffrn_reflns_theta_min         2.205
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.632
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6688
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 1803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.034(12)
_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     209
_refine_ls_number_reflns         4491
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0182
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0136P)^2^+0.6694P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0375
_refine_ls_wR_factor_ref         0.0381
_reflns_Friedel_coverage         0.763
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                4269
_reflns_number_total             4491
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00829_si_003.cif
_cod_data_source_block           2083
_cod_database_code               4038356
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.894
_shelx_estimated_absorpt_t_min   0.854