#------------------------------------------------------------------------------
#$Date: 2019-11-07 22:17:27 +0100 (jue 07 de nov de 2019) $
#$Revision: 223980 $
#$URL: svn://www.crystallography.net/cod/cif/7/70/06/7700626.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_7700626
loop_
_publ_author_name
'Thapa, Rajesh'
'Kilyanek, Stefan M.'
_publ_section_title
;
 Synthesis and structural characterization of 20-membered macrocyclic
 rings bearing trans-chelating bis(N-heterocyclic carbene) ligands and the
 catalytic activity of their palladium(ii) complexes.
;
_journal_issue                   33
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              12577
_journal_page_last               12590
_journal_paper_doi               10.1039/c9dt02147g
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety
'0.57(C40 H46 Cl2 N6 Pd), 0.43(C40 H46 Br Cl N6 Pd)'
_chemical_formula_sum            'C40 H46 Br0.43 Cl1.57 N6 Pd'
_chemical_formula_weight         807.24
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-29 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.665(19)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.462(17)
_cell_length_b                   10.751(15)
_cell_length_c                   14.335(19)
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      19.24
_cell_measurement_theta_min      2.39
_cell_volume                     1866(4)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX3 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'Mercury (CCDC, 2017)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14735
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        22.722
_diffrn_reflns_theta_max         22.722
_diffrn_reflns_theta_min         1.950
_exptl_absorpt_coefficient_mu    1.107
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/4 (Sheldrick, 2015c)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_description       block
_exptl_crystal_F_000             831
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         2508
_refine_ls_number_restraints     667
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0879
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1400P)²+20.3000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2480
_refine_ls_wR_factor_ref         0.2636
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1897
_reflns_number_total             2508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt02147g2.cif
_cod_data_source_block           17191a
_cod_depositor_comments
'Adding full bibliography for 7700623--7700627.cif.'
_cod_database_code               7700626
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.660
_shelx_estimated_absorpt_t_max   0.907
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, 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 0.500000 0.500000 0.500000 0.0501(6) Uani 1 2 d S . P . .
Cl1 Cl 0.3362(10) 0.4263(19) 0.4186(15) 0.053(3) Uani 0.786(11) 1 d . . P A 1
Br1 Br 0.3028(17) 0.426(3) 0.418(2) 0.043(4) Uani 0.214(11) 1 d . . P A 2
N1 N 0.4247(8) 0.7588(9) 0.5370(7) 0.054(2) Uani 1 1 d . . . . .
N2 N 0.4226(8) 0.7376(9) 0.3861(7) 0.055(2) Uani 1 1 d . . . . .
N3 N 0.5997(16) 0.5008(10) 0.2679(13) 0.078(2) Uani 0.590(15) 1 d D U P B 1
N3' N 0.606(2) 0.5116(13) 0.2428(16) 0.078(2) Uani 0.410(15) 1 d D U P B 2
C1 C 0.4464(10) 0.6775(11) 0.4728(9) 0.049(3) Uani 1 1 d . . . . .
C2 C 0.3899(9) 0.8742(10) 0.4943(10) 0.054(3) Uani 1 1 d . . . . .
C3 C 0.3595(12) 0.9843(12) 0.5293(13) 0.075(4) Uani 1 1 d . . . . .
H3 H 0.356935 0.992763 0.594728 0.090 Uiso 1 1 calc R U . . .
C4 C 0.3321(12) 1.0855(13) 0.4636(15) 0.085(4) Uani 1 1 d . . . . .
H4 H 0.313310 1.164125 0.485529 0.102 Uiso 1 1 calc R U . . .
C5 C 0.3329(12) 1.0689(15) 0.3659(15) 0.089(4) Uani 1 1 d . . . . .
H5 H 0.314176 1.137292 0.323196 0.107 Uiso 1 1 calc R U . . .
C6 C 0.3596(12) 0.9587(13) 0.3311(12) 0.078(4) Uani 1 1 d . . . . .
H6 H 0.358910 0.947976 0.265210 0.094 Uiso 1 1 calc R U . . .
C7 C 0.3883(10) 0.8611(11) 0.3976(10) 0.057(3) Uani 1 1 d . . . . .
C8 C 0.4310(12) 0.6863(12) 0.2932(9) 0.067(3) Uani 1 1 d . . . . .
H8A H 0.365800 0.713692 0.243542 0.080 Uiso 1 1 calc R U . . .
H8B H 0.428282 0.594406 0.296680 0.080 Uiso 1 1 calc R U . . .
C9 C 0.5334(14) 0.7229(12) 0.2620(10) 0.077(4) Uani 1 1 d D . . . .
H9A H 0.515779 0.728625 0.191033 0.093 Uiso 1 1 calc R U . . .
H9B H 0.557145 0.806382 0.288005 0.093 Uiso 1 1 calc R U . . .
C10 C 0.6250(13) 0.6349(13) 0.2937(11) 0.084(4) Uani 1 1 d D . . . .
H10A H 0.650739 0.641040 0.364374 0.101 Uiso 1 1 calc R U . B 1
H10B H 0.686958 0.661272 0.265865 0.101 Uiso 1 1 calc R U . B 1
C11 C 0.6879(19) 0.429(2) 0.3368(16) 0.076(2) Uani 0.590(15) 1 d D U P B 1
H11A H 0.692959 0.460122 0.402779 0.091 Uiso 0.590(15) 1 calc R U P B 1
H11B H 0.759963 0.444360 0.321020 0.091 Uiso 0.590(15) 1 calc R U P B 1
C12 C 0.665(2) 0.291(2) 0.333(2) 0.074(3) Uani 0.590(15) 1 d D U P B 1
H12A H 0.662794 0.258946 0.268265 0.089 Uiso 0.590(15) 1 calc R U P B 1
H12B H 0.724925 0.247532 0.379410 0.089 Uiso 0.590(15) 1 calc R U P B 1
C13 C 0.556(2) 0.265(5) 0.3585(14) 0.073(3) Uani 0.590(15) 1 d D U P B 1
H13A H 0.506000 0.337643 0.340806 0.088 Uiso 0.590(15) 1 calc R U P B 1
H13B H 0.519979 0.192037 0.322150 0.088 Uiso 0.590(15) 1 calc R U P B 1
C14 C 0.6039(19) 0.4840(17) 0.1626(14) 0.080(2) Uani 0.590(15) 1 d D U P B 1
H14A H 0.572499 0.558613 0.125533 0.096 Uiso 0.590(15) 1 calc R U P B 1
H14B H 0.681715 0.475695 0.158418 0.096 Uiso 0.590(15) 1 calc R U P B 1
C15 C 0.5405(15) 0.3714(16) 0.1198(10) 0.082(2) Uani 0.590(15) 1 d D U P B 1
C16 C 0.4357(17) 0.3470(19) 0.1341(16) 0.084(2) Uani 0.590(15) 1 d D U P B 1
H16 H 0.403860 0.402661 0.171466 0.100 Uiso 0.590(15) 1 calc R U P B 1
C17 C 0.3778(18) 0.243(2) 0.0947(19) 0.085(3) Uani 0.590(15) 1 d D U P B 1
H17 H 0.306504 0.227026 0.105046 0.102 Uiso 0.590(15) 1 calc R U P B 1
C18 C 0.4234(18) 0.163(2) 0.0403(16) 0.086(3) Uani 0.590(15) 1 d D U P B 1
H18 H 0.383270 0.091255 0.012863 0.103 Uiso 0.590(15) 1 calc R U P B 1
C19 C 0.5265(18) 0.1849(18) 0.0253(15) 0.085(3) Uani 0.590(15) 1 d D U P B 1
H19 H 0.557464 0.128619 -0.012255 0.103 Uiso 0.590(15) 1 calc R U P B 1
C20 C 0.5853(17) 0.2884(17) 0.0646(14) 0.084(2) Uani 0.590(15) 1 d D U P B 1
H20 H 0.656580 0.303307 0.053974 0.101 Uiso 0.590(15) 1 calc R U P B 1
C11' C 0.692(3) 0.411(3) 0.265(2) 0.077(2) Uani 0.410(15) 1 d D U P B 2
H11C H 0.766317 0.446386 0.268566 0.092 Uiso 0.410(15) 1 calc R U P B 2
H11D H 0.677300 0.347365 0.213345 0.092 Uiso 0.410(15) 1 calc R U P B 2
C12' C 0.689(3) 0.351(4) 0.360(2) 0.074(3) Uani 0.410(15) 1 d D U P B 2
H12C H 0.700437 0.417025 0.409405 0.089 Uiso 0.410(15) 1 calc R U P B 2
H12D H 0.751684 0.292543 0.377548 0.089 Uiso 0.410(15) 1 calc R U P B 2
C13' C 0.576(4) 0.276(7) 0.3631(17) 0.074(3) Uani 0.410(15) 1 d D U P B 2
H13C H 0.511152 0.329180 0.336026 0.088 Uiso 0.410(15) 1 calc R U P B 2
H13D H 0.570469 0.200182 0.323186 0.088 Uiso 0.410(15) 1 calc R U P B 2
C14' C 0.555(3) 0.5154(18) 0.1347(14) 0.080(2) Uani 0.410(15) 1 d D U P B 2
H14C H 0.490457 0.572673 0.121741 0.096 Uiso 0.410(15) 1 calc R U P B 2
H14D H 0.609222 0.547476 0.100553 0.096 Uiso 0.410(15) 1 calc R U P B 2
C15' C 0.5176(17) 0.3885(19) 0.0979(12) 0.082(2) Uani 0.410(15) 1 d D U P B 2
C16' C 0.423(2) 0.335(2) 0.117(2) 0.084(2) Uani 0.410(15) 1 d D U P B 2
H16' H 0.381360 0.378616 0.154022 0.100 Uiso 0.410(15) 1 calc R U P B 2
C17' C 0.392(2) 0.218(3) 0.082(2) 0.085(3) Uani 0.410(15) 1 d D U P B 2
H17' H 0.327786 0.179832 0.094903 0.102 Uiso 0.410(15) 1 calc R U P B 2
C18' C 0.454(2) 0.157(3) 0.029(2) 0.086(3) Uani 0.410(15) 1 d D U P B 2
H18' H 0.431050 0.075863 0.005379 0.103 Uiso 0.410(15) 1 calc R U P B 2
C19' C 0.547(3) 0.207(2) 0.009(2) 0.085(3) Uani 0.410(15) 1 d D U P B 2
H19' H 0.588275 0.162446 -0.027572 0.102 Uiso 0.410(15) 1 calc R U P B 2
C20' C 0.579(2) 0.324(2) 0.0439(18) 0.084(3) Uani 0.410(15) 1 d D U P B 2
H20' H 0.643069 0.361117 0.030935 0.101 Uiso 0.410(15) 1 calc R U P B 2
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'
N N 0.0061 0.0033 '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'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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
C1 Pd1 C1 180.0 . 3_666
C1 Pd1 Cl1 89.2(6) . 3_666
C1 Pd1 Cl1 90.8(6) 3_666 3_666
C1 Pd1 Cl1 90.8(6) . .
C1 Pd1 Cl1 89.2(6) 3_666 .
Cl1 Pd1 Cl1 180.0 3_666 .
C1 Pd1 Br1 88.2(7) . .
C1 Pd1 Br1 91.8(7) 3_666 .
C1 Pd1 Br1 91.8(7) . 3_666
C1 Pd1 Br1 88.2(7) 3_666 3_666
Cl1 Pd1 Br1 5.5(10) 3_666 3_666
Cl1 Pd1 Br1 174.5(10) . 3_666
C1 N1 C2 111.6(10) . .
C1 N1 C13 125(2) . 3_666
C2 N1 C13 124(2) . 3_666
C1 N1 C13' 123(3) . 3_666
C2 N1 C13' 125(3) . 3_666
C13 N1 C13' 11(3) 3_666 3_666
C1 N2 C7 110.1(10) . .
C1 N2 C8 126.8(10) . .
C7 N2 C8 123.1(10) . .
C10 N3 C11 104.5(16) . .
C10 N3 C14 107.5(12) . .
C11 N3 C14 113.4(14) . .
C11' N3' C10 121(2) . .
C11' N3' C14' 109.9(14) . .
C10 N3' C14' 116.5(14) . .
N1 C1 N2 106.2(10) . .
N1 C1 Pd1 126.2(8) . .
N2 C1 Pd1 127.5(9) . .
C3 C2 C7 120.8(13) . .
C3 C2 N1 133.2(14) . .
C7 C2 N1 105.9(10) . .
C2 C3 C4 117.3(16) . .
C2 C3 H3 121.3 . .
C4 C3 H3 121.3 . .
C5 C4 C3 120.1(15) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C6 C5 C4 122.3(15) . .
C6 C5 H5 118.9 . .
C4 C5 H5 118.9 . .
C5 C6 C7 116.6(16) . .
C5 C6 H6 121.7 . .
C7 C6 H6 121.7 . .
C2 C7 C6 122.8(13) . .
C2 C7 N2 106.1(10) . .
C6 C7 N2 131.0(14) . .
N2 C8 C9 114.8(11) . .
N2 C8 H8A 108.6 . .
C9 C8 H8A 108.6 . .
N2 C8 H8B 108.6 . .
C9 C8 H8B 108.6 . .
H8A C8 H8B 107.5 . .
C10 C9 C8 113.1(12) . .
C10 C9 H9A 109.0 . .
C8 C9 H9A 109.0 . .
C10 C9 H9B 109.0 . .
C8 C9 H9B 109.0 . .
H9A C9 H9B 107.8 . .
C9 C10 N3 116.0(14) . .
C9 C10 N3' 113.4(15) . .
C9 C10 H10A 108.3 . .
N3 C10 H10A 108.3 . .
C9 C10 H10B 108.3 . .
N3 C10 H10B 108.3 . .
H10A C10 H10B 107.4 . .
N3 C11 C12 112.2(19) . .
N3 C11 H11A 109.2 . .
C12 C11 H11A 109.2 . .
N3 C11 H11B 109.2 . .
C12 C11 H11B 109.2 . .
H11A C11 H11B 107.9 . .
C13 C12 C11 110(3) . .
C13 C12 H12A 109.6 . .
C11 C12 H12A 109.6 . .
C13 C12 H12B 109.6 . .
C11 C12 H12B 109.6 . .
H12A C12 H12B 108.1 . .
N1 C13 C12 109.3(19) 3_666 .
N1 C13 H13A 109.8 3_666 .
C12 C13 H13A 109.8 . .
N1 C13 H13B 109.8 3_666 .
C12 C13 H13B 109.8 . .
H13A C13 H13B 108.3 . .
C15 C14 N3 111.2(11) . .
C15 C14 H14A 109.4 . .
N3 C14 H14A 109.4 . .
C15 C14 H14B 109.4 . .
N3 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C20 C15 C16 118.5(18) . .
C20 C15 C14 120.5(13) . .
C16 C15 C14 121.0(13) . .
C17 C16 C15 120.7(15) . .
C17 C16 H16 119.6 . .
C15 C16 H16 119.6 . .
C18 C17 C16 119.7(17) . .
C18 C17 H17 120.1 . .
C16 C17 H17 120.1 . .
C19 C18 C17 121(2) . .
C19 C18 H18 119.7 . .
C17 C18 H18 119.7 . .
C18 C19 C20 120.2(17) . .
C18 C19 H19 119.9 . .
C20 C19 H19 119.9 . .
C19 C20 C15 120.3(16) . .
C19 C20 H20 119.9 . .
C15 C20 H20 119.9 . .
N3' C11' C12' 109(3) . .
N3' C11' H11C 109.9 . .
C12' C11' H11C 109.9 . .
N3' C11' H11D 109.9 . .
C12' C11' H11D 109.9 . .
H11C C11' H11D 108.3 . .
C11' C12' C13' 116(3) . .
C11' C12' H12C 108.2 . .
C13' C12' H12C 108.2 . .
C11' C12' H12D 108.2 . .
C13' C12' H12D 108.2 . .
H12C C12' H12D 107.4 . .
N1 C13' C12' 111(3) 3_666 .
N1 C13' H13C 109.5 3_666 .
C12' C13' H13C 109.5 . .
N1 C13' H13D 109.5 3_666 .
C12' C13' H13D 109.5 . .
H13C C13' H13D 108.1 . .
C15' C14' N3' 110.6(11) . .
C15' C14' H14C 109.5 . .
N3' C14' H14C 109.5 . .
C15' C14' H14D 109.5 . .
N3' C14' H14D 109.5 . .
H14C C14' H14D 108.1 . .
C16' C15' C20' 120.2(19) . .
C16' C15' C14' 120.7(14) . .
C20' C15' C14' 119.1(14) . .
C17' C16' C15' 119.2(16) . .
C17' C16' H16' 120.4 . .
C15' C16' H16' 120.4 . .
C18' C17' C16' 119.4(19) . .
C18' C17' H17' 120.3 . .
C16' C17' H17' 120.3 . .
C19' C18' C17' 123(2) . .
C19' C18' H18' 118.7 . .
C17' C18' H18' 118.7 . .
C18' C19' C20' 118.3(18) . .
C18' C19' H19' 120.9 . .
C20' C19' H19' 120.9 . .
C19' C20' C15' 120.3(16) . .
C19' C20' H20' 119.9 . .
C15' C20' H20' 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.029(12) .
Pd1 C1 2.029(12) 3_666
Pd1 Cl1 2.243(16) 3_666
Pd1 Cl1 2.243(16) .
Pd1 Br1 2.59(2) .
Pd1 Br1 2.59(2) 3_666
N1 C1 1.342(15) .
N1 C2 1.407(14) .
N1 C13 1.483(18) 3_666
N1 C13' 1.483(18) 3_666
N2 C1 1.369(15) .
N2 C7 1.417(16) .
N2 C8 1.468(16) .
N3 C10 1.503(15) .
N3 C11 1.504(15) .
N3 C14 1.53(2) .
N3' C11' 1.504(15) .
N3' C10 1.504(15) .
N3' C14' 1.53(2) .
C2 C3 1.373(18) .
C2 C7 1.389(18) .
C3 C4 1.43(2) .
C3 H3 0.9500 .
C4 C5 1.41(2) .
C4 H4 0.9500 .
C5 C6 1.36(2) .
C5 H5 0.9500 .
C6 C7 1.405(18) .
C6 H6 0.9500 .
C8 C9 1.501(19) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.47(2) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C12 1.51(2) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.51(2) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C14 C15 1.50(2) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C20 1.394(14) .
C15 C16 1.394(14) .
C16 C17 1.377(18) .
C16 H16 0.9500 .
C17 C18 1.374(16) .
C17 H17 0.9500 .
C18 C19 1.373(16) .
C18 H18 0.9500 .
C19 C20 1.377(18) .
C19 H19 0.9500 .
C20 H20 0.9500 .
C11' C12' 1.51(2) .
C11' H11C 0.9900 .
C11' H11D 0.9900 .
C12' C13' 1.63(6) .
C12' H12C 0.9900 .
C12' H12D 0.9900 .
C13' H13C 0.9900 .
C13' H13D 0.9900 .
C14' C15' 1.50(2) .
C14' H14C 0.9900 .
C14' H14D 0.9900 .
C15' C16' 1.394(15) .
C15' C20' 1.394(14) .
C16' C17' 1.377(18) .
C16' H16' 0.9500 .
C17' C18' 1.374(16) .
C17' H17' 0.9500 .
C18' C19' 1.373(16) .
C18' H18' 0.9500 .
C19' C20' 1.377(18) .
C19' H19' 0.9500 .
C20' H20' 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C6 H6 Br1 0.95 2.92 3.68(3) 138.4 2 yes
C8 H8B Cl1 0.99 2.93 3.67(2) 131.9 . yes
C8 H8B N3 0.99 2.48 2.98(2) 110.8 . yes
C11 H11A Cl1 0.99 2.94 3.91(3) 168.3 3_666 yes
C13 H13A Cl1 0.99 2.78 3.51(4) 131.0 . yes
C12' H12C Br1 0.99 3.00 3.97(5) 165.1 3_666 yes
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C2 N1 C1 N2 -1.9(14) . .
C13 N1 C1 N2 -176.8(17) 3_666 .
C13' N1 C1 N2 171(2) 3_666 .
C2 N1 C1 Pd1 179.5(8) . .
C13 N1 C1 Pd1 5(2) 3_666 .
C13' N1 C1 Pd1 -8(3) 3_666 .
C7 N2 C1 N1 1.9(14) . .
C8 N2 C1 N1 -178.8(11) . .
C7 N2 C1 Pd1 -179.6(9) . .
C8 N2 C1 Pd1 -0.3(18) . .
C1 N1 C2 C3 -179.6(14) . .
C13 N1 C2 C3 -5(2) 3_666 .
C13' N1 C2 C3 8(3) 3_666 .
C1 N1 C2 C7 1.2(14) . .
C13 N1 C2 C7 176.2(16) 3_666 .
C13' N1 C2 C7 -171(3) 3_666 .
C7 C2 C3 C4 -3(2) . .
N1 C2 C3 C4 177.8(12) . .
C2 C3 C4 C5 2(2) . .
C3 C4 C5 C6 0(2) . .
C4 C5 C6 C7 -1(2) . .
C3 C2 C7 C6 2(2) . .
N1 C2 C7 C6 -178.7(11) . .
C3 C2 C7 N2 -179.3(11) . .
N1 C2 C7 N2 0.0(13) . .
C5 C6 C7 C2 0(2) . .
C5 C6 C7 N2 -178.2(13) . .
C1 N2 C7 C2 -1.2(14) . .
C8 N2 C7 C2 179.5(11) . .
C1 N2 C7 C6 177.3(13) . .
C8 N2 C7 C6 -2(2) . .
C1 N2 C8 C9 -99.9(15) . .
C7 N2 C8 C9 79.4(16) . .
N2 C8 C9 C10 90.9(14) . .
C8 C9 C10 N3 53.3(18) . .
C8 C9 C10 N3' 70.1(19) . .
C11 N3 C10 C9 -159.7(14) . .
C14 N3 C10 C9 79.5(18) . .
C11' N3' C10 C9 179.0(19) . .
C14' N3' C10 C9 41(3) . .
C10 N3 C11 C12 170.1(17) . .
C14 N3 C11 C12 -73(2) . .
N3 C11 C12 C13 -60(3) . .
C11 C12 C13 N1 -93(4) . 3_666
C10 N3 C14 C15 -158.7(13) . .
C11 N3 C14 C15 86.3(18) . .
N3 C14 C15 C20 -134.4(14) . .
N3 C14 C15 C16 45.6(14) . .
C20 C15 C16 C17 0.1(4) . .
C14 C15 C16 C17 -179.9(3) . .
C15 C16 C17 C18 -0.3(6) . .
C16 C17 C18 C19 0.3(8) . .
C17 C18 C19 C20 -0.2(8) . .
C18 C19 C20 C15 0.0(8) . .
C16 C15 C20 C19 0.0(6) . .
C14 C15 C20 C19 -180.0(4) . .
C10 N3' C11' C12' 76(4) . .
C14' N3' C11' C12' -144(3) . .
N3' C11' C12' C13' 65(5) . .
C11' C12' C13' N1 -170(4) . 3_666
C11' N3' C14' C15' 50(3) . .
C10 N3' C14' C15' -167.3(18) . .
N3' C14' C15' C16' 74(2) . .
N3' C14' C15' C20' -106(2) . .
C20' C15' C16' C17' 0.0(4) . .
C14' C15' C16' C17' -180.0(3) . .
C15' C16' C17' C18' -0.1(6) . .
C16' C17' C18' C19' 0.2(8) . .
C17' C18' C19' C20' -0.2(8) . .
C18' C19' C20' C15' 0.1(8) . .
C16' C15' C20' C19' 0.0(6) . .
C14' C15' C20' C19' 180.0(4) . .
