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_4038357
_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      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.894(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.3932(3)
_cell_length_b                   13.9575(4)
_cell_length_c                   17.1315(5)
_cell_measurement_reflns_used    9853
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.507
_cell_measurement_theta_min      2.480
_cell_volume                     1963.84(11)
_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 1.000
_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  0.0467
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            68196
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.521
_diffrn_reflns_theta_min         1.899
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.625
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/4'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.755
_exptl_crystal_description       block
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.778
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.084
_refine_ls_abs_structure_details
;
 Flack x determined using 3646 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         9033
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0268
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0245P)^2^+0.9204P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0539
_refine_ls_wR_factor_ref         0.0556
_reflns_Friedel_coverage         0.921
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8210
_reflns_number_total             9033
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00829_si_004.cif
_cod_data_source_block           2084
_cod_depositor_comments
;

2025-07-29
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H54 Cl10 N4 Pd2'
_cod_original_formula_weight         1038.07
_cod_original_formula_moiety         '2(C14 H26 Cl2 N2 Pd), 2(C H Cl3)'
_cod_original_formula_units_Z            2
_cod_original_cell_volume        1963.83(11)
_cod_database_code               4038357
_shelx_shelxl_version_number     2017/1