#------------------------------------------------------------------------------
#$Date: 2019-11-07 23:17:27 +0200 (Thu, 07 Nov 2019) $
#$Revision: 223980 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/70/06/7700623.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_7700623
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         'C32 H42 Cl2 N6 Pd'
_chemical_formula_sum            'C32 H42 Cl2 N6 Pd'
_chemical_formula_weight         688.01
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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
;
2019-07-18 deposited with the CCDC.    2019-07-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.685(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.612(4)
_cell_length_b                   8.505(2)
_cell_length_c                   16.280(5)
_cell_measurement_reflns_used    9819
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.51
_cell_volume                     1602.4(8)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'Mercury (CCDC, 2016)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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  0.0474
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            81927
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.581
_diffrn_reflns_theta_min         1.760
_exptl_absorpt_coefficient_mu    0.777
_exptl_absorpt_correction_T_max  0.812
_exptl_absorpt_correction_T_min  0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'TWINABS 2012/1 (Sheldrick, 2015c)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_refine_diff_density_max         3.153
_refine_diff_density_min         -1.415
_refine_diff_density_rms         0.316
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         14455
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1231
_refine_ls_R_factor_gt           0.0751
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0950P)²+6.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1975
_refine_ls_wR_factor_ref         0.2326
_reflns_Friedel_coverage         0.000
_reflns_number_gt                9254
_reflns_number_total             14455
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9dt02147g2.cif
_cod_data_source_block           16065c
_cod_depositor_comments
'Adding full bibliography for 7700623--7700627.cif.'
_cod_database_code               7700623
_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   0.757
_shelx_estimated_absorpt_t_max   0.812
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Pd1 Pd 0.500000 0.500000 0.500000 0.0196(2) Uani 1 2 d S . P
Cl1 Cl 0.57761(14) 0.35879(17) 0.61477(9) 0.0207(4) Uani 1 1 d . . .
N1 N 0.5818(5) 0.8285(6) 0.5540(3) 0.0228(11) Uani 1 1 d . . .
N2 N 0.4581(5) 0.7396(7) 0.6331(3) 0.0229(11) Uani 1 1 d . . .
N3 N 0.1971(5) 0.4477(8) 0.5588(4) 0.0266(12) Uani 1 1 d . . .
C1 C 0.5148(6) 0.7028(8) 0.5661(4) 0.0215(13) Uani 1 1 d . . .
C2 C 0.5679(6) 0.9431(8) 0.6133(4) 0.0271(14) Uani 1 1 d . . .
H2 H 0.606104 1.041815 0.618139 0.032 Uiso 1 1 calc R U .
C3 C 0.4900(6) 0.8873(8) 0.6625(4) 0.0274(14) Uani 1 1 d . . .
H3 H 0.462228 0.939244 0.708663 0.033 Uiso 1 1 calc R U .
C4 C 0.3732(6) 0.6421(9) 0.6708(4) 0.0269(14) Uani 1 1 d . . .
H4A H 0.384143 0.653301 0.731508 0.032 Uiso 1 1 calc R U .
H4B H 0.386314 0.530415 0.657191 0.032 Uiso 1 1 calc R U .
C5 C 0.2489(6) 0.6870(9) 0.6416(5) 0.0301(15) Uani 1 1 d . . .
H5A H 0.196840 0.649618 0.682626 0.036 Uiso 1 1 calc R U .
H5B H 0.243030 0.803014 0.639057 0.036 Uiso 1 1 calc R U .
C6 C 0.2079(6) 0.6198(9) 0.5576(4) 0.0294(15) Uani 1 1 d . . .
H6A H 0.131905 0.666246 0.539284 0.035 Uiso 1 1 calc R U .
H6B H 0.263141 0.649905 0.517187 0.035 Uiso 1 1 calc R U .
C7 C 0.1957(6) 0.3812(9) 0.4754(4) 0.0280(15) Uani 1 1 d . . .
H7A H 0.257138 0.431902 0.445896 0.034 Uiso 1 1 calc R U .
H7B H 0.120601 0.405481 0.444817 0.034 Uiso 1 1 calc R U .
C8 C 0.2142(6) 0.2043(9) 0.4758(5) 0.0289(15) Uani 1 1 d . . .
H8A H 0.199251 0.163918 0.418893 0.035 Uiso 1 1 calc R U .
H8B H 0.157617 0.154649 0.510038 0.035 Uiso 1 1 calc R U .
C9 C 0.3360(6) 0.1568(8) 0.5090(4) 0.0262(14) Uani 1 1 d . . .
H9A H 0.361249 0.224411 0.556608 0.031 Uiso 1 1 calc R U .
H9B H 0.335073 0.046642 0.528539 0.031 Uiso 1 1 calc R U .
C10 C 0.0953(6) 0.3976(9) 0.6004(5) 0.0296(15) Uani 1 1 d . . .
H10A H 0.031760 0.374043 0.557874 0.036 Uiso 1 1 calc R U .
H10B H 0.070007 0.486401 0.633853 0.036 Uiso 1 1 calc R U .
C11 C 0.1143(6) 0.2562(9) 0.6553(5) 0.0293(15) Uani 1 1 d . . .
C12 C 0.2159(6) 0.2403(9) 0.7068(4) 0.0296(15) Uani 1 1 d . . .
H12 H 0.275192 0.316882 0.705026 0.036 Uiso 1 1 calc R U .
C13 C 0.2310(7) 0.1145(10) 0.7601(5) 0.0343(17) Uani 1 1 d . . .
H13 H 0.300233 0.105370 0.795097 0.041 Uiso 1 1 calc R U .
C14 C 0.1453(7) 0.0012(9) 0.7627(5) 0.0332(17) Uani 1 1 d . . .
H14 H 0.155793 -0.084605 0.799891 0.040 Uiso 1 1 calc R U .
C15 C 0.0447(8) 0.0129(10) 0.7113(5) 0.0371(18) Uani 1 1 d . . .
H15 H -0.013072 -0.066122 0.711857 0.045 Uiso 1 1 calc R U .
C16 C 0.0289(7) 0.1423(10) 0.6585(5) 0.0341(17) Uani 1 1 d . . .
H16 H -0.041041 0.152522 0.624431 0.041 Uiso 1 1 calc R U .
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'
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 90.14(18) . .
C1 Pd1 Cl1 89.86(18) 3_666 .
C1 Pd1 Cl1 89.86(18) . 3_666
C1 Pd1 Cl1 90.14(18) 3_666 3_666
Cl1 Pd1 Cl1 180.00(5) . 3_666
C1 N1 C2 110.7(6) . .
C1 N1 C9 126.1(6) . 3_666
C2 N1 C9 123.2(6) . 3_666
C1 N2 C3 110.7(6) . .
C1 N2 C4 126.6(6) . .
C3 N2 C4 122.7(6) . .
C6 N3 C7 111.5(6) . .
C6 N3 C10 111.5(6) . .
C7 N3 C10 111.4(6) . .
N1 C1 N2 105.0(6) . .
N1 C1 Pd1 128.4(5) . .
N2 C1 Pd1 126.6(5) . .
C3 C2 N1 106.8(6) . .
C3 C2 H2 126.6 . .
N1 C2 H2 126.6 . .
C2 C3 N2 106.8(6) . .
C2 C3 H3 126.6 . .
N2 C3 H3 126.6 . .
N2 C4 C5 112.3(6) . .
N2 C4 H4A 109.2 . .
C5 C4 H4A 109.2 . .
N2 C4 H4B 109.2 . .
C5 C4 H4B 109.2 . .
H4A C4 H4B 107.9 . .
C6 C5 C4 113.9(6) . .
C6 C5 H5A 108.8 . .
C4 C5 H5A 108.8 . .
C6 C5 H5B 108.8 . .
C4 C5 H5B 108.8 . .
H5A C5 H5B 107.7 . .
N3 C6 C5 112.5(6) . .
N3 C6 H6A 109.1 . .
C5 C6 H6A 109.1 . .
N3 C6 H6B 109.1 . .
C5 C6 H6B 109.1 . .
H6A C6 H6B 107.8 . .
N3 C7 C8 112.7(6) . .
N3 C7 H7A 109.1 . .
C8 C7 H7A 109.1 . .
N3 C7 H7B 109.1 . .
C8 C7 H7B 109.1 . .
H7A C7 H7B 107.8 . .
C7 C8 C9 112.9(6) . .
C7 C8 H8A 109.0 . .
C9 C8 H8A 109.0 . .
C7 C8 H8B 109.0 . .
C9 C8 H8B 109.0 . .
H8A C8 H8B 107.8 . .
N1 C9 C8 111.6(6) 3_666 .
N1 C9 H9A 109.3 3_666 .
C8 C9 H9A 109.3 . .
N1 C9 H9B 109.3 3_666 .
C8 C9 H9B 109.3 . .
H9A C9 H9B 108.0 . .
N3 C10 C11 114.9(6) . .
N3 C10 H10A 108.5 . .
C11 C10 H10A 108.5 . .
N3 C10 H10B 108.5 . .
C11 C10 H10B 108.5 . .
H10A C10 H10B 107.5 . .
C16 C11 C12 118.7(7) . .
C16 C11 C10 120.6(7) . .
C12 C11 C10 120.6(7) . .
C13 C12 C11 120.7(8) . .
C13 C12 H12 119.7 . .
C11 C12 H12 119.7 . .
C12 C13 C14 120.2(8) . .
C12 C13 H13 119.9 . .
C14 C13 H13 119.9 . .
C15 C14 C13 120.2(7) . .
C15 C14 H14 119.9 . .
C13 C14 H14 119.9 . .
C14 C15 C16 119.3(8) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C11 C16 C15 120.9(8) . .
C11 C16 H16 119.5 . .
C15 C16 H16 119.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 C1 2.033(7) .
Pd1 C1 2.033(7) 3_666
Pd1 Cl1 2.3389(15) .
Pd1 Cl1 2.3389(15) 3_666
N1 C1 1.346(9) .
N1 C2 1.391(9) .
N1 C9 1.462(9) 3_666
N2 C1 1.356(8) .
N2 C3 1.385(9) .
N2 C4 1.462(9) .
N3 C6 1.469(10) .
N3 C7 1.470(9) .
N3 C10 1.472(9) .
C2 C3 1.342(11) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C4 C5 1.530(10) .
C4 H4A 0.9900 .
C4 H4B 0.9900 .
C5 C6 1.522(10) .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C6 H6A 0.9900 .
C6 H6B 0.9900 .
C7 C8 1.520(11) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.527(10) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C10 C11 1.505(11) .
C10 H10A 0.9900 .
C10 H10B 0.9900 .
C11 C16 1.389(11) .
C11 C12 1.397(10) .
C12 C13 1.380(11) .
C12 H12 0.9500 .
C13 C14 1.388(12) .
C13 H13 0.9500 .
C14 C15 1.384(13) .
C14 H14 0.9500 .
C15 C16 1.399(12) .
C15 H15 0.9500 .
C16 H16 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
C2 H2 Cl1 0.95 2.72 3.537(7) 145.1 1_565 yes
C4 H4B Cl1 0.99 2.79 3.554(7) 134.2 . yes
C6 H6B Cl1 0.99 2.95 3.906(7) 163.2 3_666 yes
C7 H7A Cl1 0.99 2.85 3.821(8) 166.2 3_666 yes
C9 H9A Cl1 0.99 2.85 3.605(7) 133.6 . 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 0.4(7) . .
C9 N1 C1 N2 176.9(6) 3_666 .
C2 N1 C1 Pd1 -179.4(5) . .
C9 N1 C1 Pd1 -2.9(10) 3_666 .
C3 N2 C1 N1 -0.2(7) . .
C4 N2 C1 N1 179.1(6) . .
C3 N2 C1 Pd1 179.7(5) . .
C4 N2 C1 Pd1 -1.1(10) . .
C1 N1 C2 C3 -0.5(8) . .
C9 N1 C2 C3 -177.1(6) 3_666 .
N1 C2 C3 N2 0.4(8) . .
C1 N2 C3 C2 -0.2(8) . .
C4 N2 C3 C2 -179.4(6) . .
C1 N2 C4 C5 -96.8(8) . .
C3 N2 C4 C5 82.3(8) . .
N2 C4 C5 C6 80.2(8) . .
C7 N3 C6 C5 -161.0(6) . .
C10 N3 C6 C5 73.8(7) . .
C4 C5 C6 N3 67.1(8) . .
C6 N3 C7 C8 166.0(6) . .
C10 N3 C7 C8 -68.7(7) . .
N3 C7 C8 C9 -68.2(8) . .
C7 C8 C9 N1 -81.2(7) . 3_666
C6 N3 C10 C11 -139.5(7) . .
C7 N3 C10 C11 95.3(7) . .
N3 C10 C11 C16 -141.0(7) . .
N3 C10 C11 C12 41.9(10) . .
C16 C11 C12 C13 -0.4(11) . .
C10 C11 C12 C13 176.8(7) . .
C11 C12 C13 C14 0.5(11) . .
C12 C13 C14 C15 0.6(12) . .
C13 C14 C15 C16 -1.9(12) . .
C12 C11 C16 C15 -0.9(11) . .
C10 C11 C16 C15 -178.1(7) . .
C14 C15 C16 C11 2.0(12) . .
