#------------------------------------------------------------------------------
#$Date: 2020-05-14 01:34:23 +0300 (Thu, 14 May 2020) $
#$Revision: 252030 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038360.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4038360
loop_
_publ_author_name
'Higgins, Tyler'
'Winkler, Jeffrey D.'
_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         'C11 H22 Cl2 N2 Pd, C H Cl3'
_chemical_formula_sum            'C12 H23 Cl5 N2 Pd'
_chemical_formula_weight         478.97
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-30
_audit_creation_method
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.6817(4)
_cell_length_b                   7.8188(2)
_cell_length_c                   16.3276(5)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.51
_cell_measurement_theta_min      3.23
_cell_volume                     1746.64(9)
_computing_data_collection       'Bruker APEX3 v2016.1-0'
_computing_data_reduction        'Bruker SAINT v8.37A'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CMOS area detector'
_diffrn_measurement_device_type  'Bruker D8QUEST'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25696
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         2.978
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    1.819
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2014/5'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.821
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.377
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.077
_refine_ls_abs_structure_details
;
 Flack x determined using 1794 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.020(13)
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3993
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.105
_refine_ls_R_factor_all          0.0200
_refine_ls_R_factor_gt           0.0183
_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/[σ²(Fo²)+(0.0157P)²+0.3479P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0394
_refine_ls_wR_factor_ref         0.0399
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3858
_reflns_number_total             3993
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo0c00829_si_006.cif
_cod_data_source_block           2077
_cod_database_code               4038360
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.83050(2) 0.36754(2) 0.39573(2) 0.00759(6) Uani 1 1 d . . . . .
Cl1 Cl 0.95591(5) 0.16845(9) 0.41014(5) 0.01216(16) Uani 1 1 d . . . . .
Cl2 Cl 0.87391(7) 0.38544(11) 0.25887(5) 0.01719(18) Uani 1 1 d . . . . .
N1 N 0.8012(2) 0.3632(3) 0.52327(17) 0.0110(5) Uani 1 1 d . . . . .
N11 N 0.7034(2) 0.5183(3) 0.37989(16) 0.0116(6) Uani 1 1 d . . . . .
C2 C 0.7438(2) 0.2029(4) 0.5390(2) 0.0133(6) Uani 1 1 d . . . . .
H2a H 0.7025 0.2207 0.5866 0.018 Uiso 1 1 calc R . . . .
H2b H 0.7888 0.1110 0.5519 0.018 Uiso 1 1 calc R . . . .
C3 C 0.6797(2) 0.1478(4) 0.4670(2) 0.0151(7) Uani 1 1 d . . . . .
H3a H 0.6477 0.0416 0.4819 0.020 Uiso 1 1 calc R . . . .
H3b H 0.7224 0.1231 0.4211 0.020 Uiso 1 1 calc R . . . .
C4 C 0.6005(2) 0.2731(4) 0.4373(2) 0.0151(7) Uani 1 1 d . . . . .
H4a H 0.5837 0.2423 0.3815 0.020 Uiso 1 1 calc R . . . .
H4b H 0.5426 0.2548 0.4705 0.020 Uiso 1 1 calc R . . . .
C5 C 0.6236(2) 0.4644(4) 0.4386(2) 0.0122(7) Uani 1 1 d . . . . .
H5 H 0.5641 0.5225 0.4203 0.016 Uiso 1 1 calc R . . . .
C6 C 0.6419(3) 0.5249(5) 0.5260(2) 0.0140(7) Uani 1 1 d . . . . .
H6a H 0.6192 0.6421 0.5306 0.019 Uiso 1 1 calc R . . . .
H6b H 0.6022 0.4560 0.5626 0.019 Uiso 1 1 calc R . . . .
C7 C 0.7471(2) 0.5178(4) 0.5557(2) 0.0128(7) Uani 1 1 d . . . . .
H7 H 0.7442 0.5046 0.6154 0.017 Uiso 1 1 calc R . . . .
C8 C 0.7990(3) 0.6891(4) 0.5393(2) 0.0174(7) Uani 1 1 d . . . . .
H8a H 0.7608 0.7798 0.5642 0.023 Uiso 1 1 calc R . . . .
H8b H 0.8620 0.6868 0.5666 0.023 Uiso 1 1 calc R . . . .
C9 C 0.8154(2) 0.7336(4) 0.4497(2) 0.0157(7) Uani 1 1 d . . . . .
H9a H 0.8335 0.8534 0.4465 0.021 Uiso 1 1 calc R . . . .
H9b H 0.8708 0.6677 0.4301 0.021 Uiso 1 1 calc R . . . .
C10 C 0.7309(2) 0.7040(4) 0.3917(3) 0.0152(6) Uani 1 1 d . . . . .
H10a H 0.6743 0.7652 0.4122 0.020 Uiso 1 1 calc R . . . .
H10b H 0.7474 0.7524 0.3388 0.020 Uiso 1 1 calc R . . . .
C12 C 0.8934(3) 0.3540(5) 0.5722(2) 0.0160(7) Uani 1 1 d . . . . .
H12a H 0.9279 0.2509 0.5586 0.024 Uiso 1 1 calc GR . . . .
H12b H 0.8778 0.3539 0.6295 0.024 Uiso 1 1 calc GR . . . .
H12c H 0.9336 0.4511 0.5598 0.024 Uiso 1 1 calc GR . . . .
C13 C 0.6605(3) 0.5019(5) 0.2960(2) 0.0174(8) Uani 1 1 d . . . . .
H13a H 0.7057 0.5463 0.2564 0.026 Uiso 1 1 calc GR . . . .
H13b H 0.6005 0.5652 0.2933 0.026 Uiso 1 1 calc GR . . . .
H13c H 0.6478 0.3836 0.2844 0.026 Uiso 1 1 calc GR . . . .
Cl3 Cl 0.55333(6) -0.19836(11) 0.73748(6) 0.02029(18) Uani 1 1 d . . . . .
Cl4 Cl 0.51433(7) 0.06297(12) 0.61671(5) 0.02214(19) Uani 1 1 d . . . . .
Cl5 Cl 0.37053(6) -0.00923(11) 0.74109(6) 0.02073(18) Uani 1 1 d . . . . .
C14 C 0.4969(3) 0.0019(4) 0.7197(2) 0.0161(7) Uani 1 1 d . . . . .
H14 H 0.5269 0.0878 0.7554 0.021 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Pd1 Cl1 87.07(3) . . ?
N1 Pd1 Cl1 91.67(8) . . ?
N1 Pd1 Cl2 175.26(8) . . ?
N11 Pd1 Cl1 171.88(8) . . ?
N11 Pd1 Cl2 93.39(7) . . ?
N11 Pd1 N1 88.50(10) . . ?
C2 N1 Pd1 106.29(19) . . ?
C2 N1 C7 110.5(3) . . ?
C7 N1 Pd1 115.0(2) . . ?
C12 N1 Pd1 111.5(2) . . ?
C12 N1 C2 108.1(3) . . ?
C12 N1 C7 105.3(3) . . ?
C5 N11 Pd1 111.10(19) . . ?
C10 N11 Pd1 108.36(18) . . ?
C10 N11 C5 111.5(2) . . ?
C13 N11 Pd1 112.7(2) . . ?
C13 N11 C5 105.9(3) . . ?
C13 N11 C10 107.3(3) . . ?
N1 C2 C3 113.8(3) . . ?
C2 C3 C4 117.8(3) . . ?
C5 C4 C3 118.2(3) . . ?
N11 C5 C4 114.4(3) . . ?
N11 C5 C6 112.9(3) . . ?
C6 C5 C4 110.5(3) . . ?
C7 C6 C5 116.3(3) . . ?
N1 C7 C6 112.4(3) . . ?
N1 C7 C8 114.1(3) . . ?
C6 C7 C8 110.5(3) . . ?
C9 C8 C7 115.8(3) . . ?
C10 C9 C8 117.0(3) . . ?
N11 C10 C9 114.6(3) . . ?
Cl4 C14 Cl3 109.70(19) . . ?
Cl4 C14 Cl5 109.5(2) . . ?
Cl5 C14 Cl3 110.54(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Cl1 2.3286(7) . ?
Pd1 Cl2 2.3164(9) . ?
Pd1 N1 2.121(3) . ?
Pd1 N11 2.117(3) . ?
N1 C2 1.502(4) . ?
N1 C7 1.514(4) . ?
N1 C12 1.494(4) . ?
N11 C5 1.512(4) . ?
N11 C10 1.512(4) . ?
N11 C13 1.496(4) . ?
C2 C3 1.528(5) . ?
C3 C4 1.539(5) . ?
C4 C5 1.529(5) . ?
C5 C6 1.524(5) . ?
C6 C7 1.520(5) . ?
C7 C8 1.540(5) . ?
C8 C9 1.522(5) . ?
C9 C10 1.513(5) . ?
Cl3 C14 1.770(4) . ?
Cl4 C14 1.764(4) . ?
Cl5 C14 1.766(4) . ?
