#------------------------------------------------------------------------------
#$Date: 2019-11-24 07:56:50 +0100 (dom 24 de nov de 2019) $
#$Revision: 237392 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/82/4088220.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_4088220
loop_
_publ_author_name
'Kinzhalov, Mikhail A.'
'Timofeeva, Svetlana A.'
'Luzyanin, Konstantin V.'
'Boyarskiy, Vadim P.'
'Yakimanskiy, Anton A.'
'Haukka, Matti'
'Kukushkin, Vadim Yu.'
_publ_section_title
;
 Palladium(II)-Mediated Addition of Benzenediamines to Isocyanides:
 Generation of Three Types of Diaminocarbene Ligands Depending on the
 Isomeric Structure of the Nucleophile
;
_journal_issue                   2
_journal_name_full               Organometallics
_journal_page_first              218
_journal_paper_doi               10.1021/acs.organomet.5b00936
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C22 H18 Cl6 N4 Pd, 2(C2 H3 N)'
_chemical_formula_sum            'C26 H24 Cl6 N6 Pd'
_chemical_formula_weight         739.61
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.170(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.9639(8)
_cell_length_b                   15.2591(9)
_cell_length_c                   15.1561(9)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.69
_cell_measurement_theta_min      2.23
_cell_volume                     3144.5(3)
_computing_cell_refinement       'SAINT (Bruker AXS, 2009)'
_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_data_reduction        'SAINT (Bruker AXS, 2009)'
_computing_molecular_graphics
'CrystaMaker (CrystalMaker Software ltd., 2011)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SUPERFLIP (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device       '62mm x 62mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Bruker KAPPA APEX II DUO CCD'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_radiation_monochromator  'curved graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0540
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            48807
_diffrn_reflns_theta_full        31.00
_diffrn_reflns_theta_max         31.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    1.127
_exptl_absorpt_correction_T_max  0.8350
_exptl_absorpt_correction_T_min  0.7682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1480
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_refine_diff_density_max         1.518
_refine_diff_density_min         -1.120
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.101
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         9943
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.101
_refine_ls_R_factor_all          0.0943
_refine_ls_R_factor_gt           0.0449
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0402P)²+4.7766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.1154
_reflns_number_gt                6490
_reflns_number_total             9943
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om5b00936_si_008.cif
_cod_data_source_block           km339
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4088220
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.454823(18) 0.122273(15) 0.498430(16) 0.01795(7) Uani 1 1 d . . .
Cl1 Cl 0.34046(6) 0.05748(5) 0.57334(6) 0.02394(16) Uani 1 1 d . . .
Cl2 Cl 0.38639(6) 0.05141(6) 0.35933(6) 0.02714(18) Uani 1 1 d . . .
Cl3 Cl 0.7439(3) 0.2583(3) 0.6936(3) 0.0342(6) Uani 0.606(5) 1 d PD A 1
Cl3A Cl 0.4735(4) 0.0735(5) 0.8265(6) 0.0363(10) Uani 0.394(5) 1 d PD A 2
Cl4 Cl 0.23376(10) 0.50405(8) 0.53333(8) 0.0547(3) Uani 1 1 d . . .
Cl5 Cl 0.27188(9) 0.50753(7) 0.33501(8) 0.0458(3) Uani 1 1 d . . .
Cl6 Cl 0.81223(18) 0.20245(18) 0.49862(15) 0.0553(6) Uani 0.770(6) 1 d PD B 3
Cl6A Cl 0.5052(13) 0.1730(19) 0.2043(18) 0.060(2) Uani 0.230(6) 1 d PD B 4
N1 N 0.5662(2) 0.14195(18) 0.67970(18) 0.0212(6) Uani 1 1 d . . .
H1 H 0.5761 0.0859 0.6714 0.025 Uiso 1 1 calc R . .
N2 N 0.5010(2) 0.27191(17) 0.61769(18) 0.0209(5) Uani 1 1 d . . .
H2 H 0.5270 0.2970 0.6699 0.025 Uiso 1 1 calc R . .
N3 N 0.5351(2) 0.27538(18) 0.43025(19) 0.0219(6) Uani 1 1 d . . .
H3 H 0.5773 0.3026 0.4047 0.026 Uiso 1 1 calc R . .
N4 N 0.6082(2) 0.14768(18) 0.4031(2) 0.0245(6) Uani 1 1 d . . .
H4 H 0.6170 0.0914 0.4148 0.029 Uiso 1 1 calc R . .
N5 N 0.4764(3) 0.6096(2) 0.2227(3) 0.0435(9) Uani 1 1 d . . .
N6 N 0.5856(3) 0.3961(2) 0.2884(3) 0.0551(12) Uani 1 1 d . . .
C1 C 0.5150(2) 0.1858(2) 0.6096(2) 0.0205(6) Uani 1 1 d . . .
C2 C 0.6073(2) 0.1769(2) 0.7684(2) 0.0227(7) Uani 1 1 d . A .
C3 C 0.6879(3) 0.2332(2) 0.7834(2) 0.0256(7) Uani 1 1 d D . .
C4 C 0.7247(3) 0.2683(2) 0.8682(3) 0.0336(8) Uani 1 1 d . A .
H4A H 0.7787 0.3077 0.8775 0.040 Uiso 1 1 calc R . .
C5 C 0.6834(3) 0.2463(3) 0.9389(3) 0.0404(10) Uani 1 1 d . . .
H5 H 0.7076 0.2719 0.9969 0.049 Uiso 1 1 calc R A .
C6 C 0.6058(3) 0.1864(3) 0.9262(3) 0.0379(9) Uani 1 1 d . A .
H6 H 0.5789 0.1698 0.9759 0.045 Uiso 1 1 calc R . .
C7 C 0.5681(3) 0.1511(2) 0.8410(2) 0.0285(7) Uani 1 1 d D . .
C8 C 0.4924(15) 0.0797(16) 0.8299(19) 0.0363(10) Uani 0.606(5) 1 d PD A 1
H8A H 0.4639 0.0781 0.8834 0.054 Uiso 0.606(5) 1 calc PR A 1
H8B H 0.5234 0.0232 0.8234 0.054 Uiso 0.606(5) 1 calc PR A 1
H8C H 0.4403 0.0911 0.7758 0.054 Uiso 0.606(5) 1 calc PR A 1
C8A C 0.736(3) 0.251(2) 0.706(2) 0.0342(6) Uani 0.394(5) 1 d PD A 2
H8AA H 0.8026 0.2734 0.7291 0.051 Uiso 0.394(5) 1 calc PR A 2
H8AB H 0.6973 0.2956 0.6656 0.051 Uiso 0.394(5) 1 calc PR A 2
H8AC H 0.7382 0.1973 0.6714 0.051 Uiso 0.394(5) 1 calc PR A 2
C9 C 0.4465(2) 0.3252(2) 0.5468(2) 0.0213(6) Uani 1 1 d . . .
C10 C 0.3772(3) 0.3816(2) 0.5684(2) 0.0279(7) Uani 1 1 d . . .
H10 H 0.3665 0.3814 0.6281 0.033 Uiso 1 1 calc R . .
C11 C 0.3236(3) 0.4380(2) 0.5046(3) 0.0334(8) Uani 1 1 d . . .
C12 C 0.3398(3) 0.4404(2) 0.4180(3) 0.0321(8) Uani 1 1 d . . .
C13 C 0.4088(3) 0.3844(2) 0.3956(2) 0.0281(7) Uani 1 1 d . . .
H13 H 0.4193 0.3853 0.3359 0.034 Uiso 1 1 calc R . .
C14 C 0.4627(3) 0.3269(2) 0.4588(2) 0.0219(6) Uani 1 1 d . . .
C15 C 0.5430(3) 0.1886(2) 0.4397(2) 0.0226(7) Uani 1 1 d . . .
C16 C 0.6659(3) 0.1865(2) 0.3463(3) 0.0266(7) Uani 1 1 d . B .
C17 C 0.7625(3) 0.2115(3) 0.3831(3) 0.0353(9) Uani 1 1 d D . .
C18 C 0.8210(3) 0.2454(3) 0.3282(4) 0.0457(11) Uani 1 1 d . B .
H18 H 0.8870 0.2623 0.3535 0.055 Uiso 1 1 calc R . .
C19 C 0.7818(4) 0.2542(3) 0.2367(3) 0.0463(12) Uani 1 1 d . . .
H19 H 0.8211 0.2776 0.1988 0.056 Uiso 1 1 calc R B .
C20 C 0.6870(4) 0.2296(3) 0.1998(3) 0.0473(12) Uani 1 1 d . B .
H20 H 0.6614 0.2359 0.1364 0.057 Uiso 1 1 calc R . .
C21 C 0.6274(3) 0.1953(3) 0.2535(3) 0.0359(9) Uani 1 1 d D . .
C22 C 0.5215(16) 0.169(2) 0.211(2) 0.060(2) Uani 0.770(6) 1 d PD B 3
H22A H 0.4783 0.2201 0.2106 0.090 Uiso 0.770(6) 1 calc PR B 3
H22B H 0.5012 0.1217 0.2456 0.090 Uiso 0.770(6) 1 calc PR B 3
H22C H 0.5169 0.1500 0.1482 0.090 Uiso 0.770(6) 1 calc PR B 3
C22A C 0.798(3) 0.218(3) 0.4870(18) 0.0553(6) Uani 0.230(6) 1 d PD B 4
H22D H 0.7791 0.2744 0.5078 0.083 Uiso 0.230(6) 1 calc PR B 4
H22E H 0.8699 0.2117 0.5039 0.083 Uiso 0.230(6) 1 calc PR B 4
H22F H 0.7681 0.1705 0.5155 0.083 Uiso 0.230(6) 1 calc PR B 4
C23 C 0.4267(3) 0.5602(3) 0.1780(3) 0.0381(9) Uani 1 1 d . . .
C24 C 0.3628(4) 0.4964(3) 0.1215(4) 0.0558(13) Uani 1 1 d . . .
H24A H 0.3611 0.5081 0.0575 0.084 Uiso 1 1 calc R . .
H24B H 0.2962 0.5011 0.1317 0.084 Uiso 1 1 calc R . .
H24C H 0.3882 0.4372 0.1371 0.084 Uiso 1 1 calc R . .
C25 C 0.6323(3) 0.4416(3) 0.2571(3) 0.0406(10) Uani 1 1 d . . .
C26 C 0.6926(4) 0.5012(3) 0.2179(4) 0.0497(12) Uani 1 1 d . . .
H26A H 0.6517 0.5494 0.1873 0.075 Uiso 1 1 calc R . .
H26B H 0.7213 0.4694 0.1739 0.075 Uiso 1 1 calc R . .
H26C H 0.7453 0.5249 0.2660 0.075 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_publ_flag
C15 Pd1 C1 86.82(13) yes
C15 Pd1 Cl2 89.95(10) ?
C1 Pd1 Cl2 176.68(9) ?
C15 Pd1 Cl1 173.45(10) ?
C1 Pd1 Cl1 89.90(9) ?
Cl2 Pd1 Cl1 93.24(3) yes
C1 N1 C2 126.3(3) ?
C1 N1 H1 116.8 ?
C2 N1 H1 116.8 ?
C1 N2 C9 123.8(3) ?
C1 N2 H2 118.1 ?
C9 N2 H2 118.1 ?
C15 N3 C14 124.3(3) ?
C15 N3 H3 117.9 ?
C14 N3 H3 117.9 ?
C15 N4 C16 126.1(3) ?
C15 N4 H4 116.9 ?
C16 N4 H4 116.9 ?
N1 C1 N2 119.2(3) ?
N1 C1 Pd1 119.3(2) ?
N2 C1 Pd1 121.4(2) ?
C7 C2 C3 119.6(3) ?
C7 C2 N1 119.2(3) ?
C3 C2 N1 121.1(3) ?
C4 C3 C2 120.4(3) ?
C4 C3 C8A 121.3(14) ?
C2 C3 C8A 118.2(14) ?
C4 C3 Cl3 120.0(3) ?
C2 C3 Cl3 119.6(3) ?
C5 C4 C3 120.1(4) ?
C5 C4 H4A 120.0 ?
C3 C4 H4A 120.0 ?
C4 C5 C6 120.2(4) ?
C4 C5 H5 119.9 ?
C6 C5 H5 119.9 ?
C7 C6 C5 120.1(4) ?
C7 C6 H6 120.0 ?
C5 C6 H6 120.0 ?
C6 C7 C2 119.4(3) ?
C6 C7 C8 119.6(11) ?
C2 C7 C8 120.7(11) ?
C6 C7 Cl3A 119.7(4) ?
C2 C7 Cl3A 120.9(4) ?
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
C3 C8A H8AA 109.5 ?
C3 C8A H8AB 109.5 ?
H8AA C8A H8AB 109.5 ?
C3 C8A H8AC 109.5 ?
H8AA C8A H8AC 109.5 ?
H8AB C8A H8AC 109.5 ?
C10 C9 C14 119.0(3) ?
C10 C9 N2 117.3(3) ?
C14 C9 N2 123.6(3) ?
C11 C10 C9 121.1(3) ?
C11 C10 H10 119.5 ?
C9 C10 H10 119.5 ?
C10 C11 C12 120.1(3) ?
C10 C11 Cl4 119.5(3) ?
C12 C11 Cl4 120.4(3) ?
C11 C12 C13 119.4(3) ?
C11 C12 Cl5 121.6(3) ?
C13 C12 Cl5 118.9(3) ?
C12 C13 C14 121.3(3) ?
C12 C13 H13 119.4 ?
C14 C13 H13 119.4 ?
C13 C14 C9 119.2(3) ?
C13 C14 N3 116.8(3) ?
C9 C14 N3 124.0(3) ?
N4 C15 N3 118.1(3) ?
N4 C15 Pd1 120.7(2) ?
N3 C15 Pd1 121.1(2) ?
C17 C16 C21 119.7(3) ?
C17 C16 N4 119.9(3) ?
C21 C16 N4 120.3(4) ?
C16 C17 C18 120.6(4) ?
C16 C17 C22A 119.0(19) ?
C18 C17 C22A 119.4(19) ?
C16 C17 Cl6 120.8(3) ?
C18 C17 Cl6 118.5(4) ?
C19 C18 C17 119.1(5) ?
C19 C18 H18 120.5 ?
C17 C18 H18 120.5 ?
C20 C19 C18 120.8(4) ?
C20 C19 H19 119.6 ?
C18 C19 H19 119.6 ?
C19 C20 C21 121.0(4) ?
C19 C20 H20 119.5 ?
C21 C20 H20 119.5 ?
C16 C21 C20 118.8(4) ?
C16 C21 C22 121.3(14) ?
C20 C21 C22 119.9(14) ?
C16 C21 Cl6A 122.2(10) ?
C20 C21 Cl6A 118.9(10) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
C17 C22A H22D 109.5 ?
C17 C22A H22E 109.5 ?
C17 C22A H22F 109.5 ?
N5 C23 C24 179.5(6) ?
C23 C24 H24A 109.5 ?
C23 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
C23 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
N6 C25 C26 179.3(5) ?
C25 C26 H26A 109.5 ?
C25 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
C25 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C15 1.958(3) yes
Pd1 C1 1.960(3) yes
Pd1 Cl2 2.3683(9) yes
Pd1 Cl1 2.3755(8) yes
Cl3 C3 1.759(5) ?
Cl3A C7 1.751(6) ?
Cl4 C11 1.740(4) ?
Cl5 C12 1.729(4) ?
Cl6 C17 1.736(5) ?
Cl6A C21 1.733(16) ?
N1 C1 1.319(4) ?
N1 C2 1.439(4) ?
N1 H1 0.8800 ?
N2 C1 1.338(4) ?
N2 C9 1.422(4) ?
N2 H2 0.8800 ?
N3 C15 1.334(4) ?
N3 C14 1.423(4) ?
N3 H3 0.8800 ?
N4 C15 1.326(4) ?
N4 C16 1.434(4) ?
N4 H4 0.8800 ?
N5 C23 1.138(5) ?
N6 C25 1.128(5) ?
C2 C7 1.392(5) ?
C2 C3 1.393(5) ?
C3 C4 1.378(5) ?
C3 C8A 1.508(18) ?
C4 C5 1.370(6) ?
C4 H4A 0.9500 ?
C5 C6 1.397(6) ?
C5 H5 0.9500 ?
C6 C7 1.387(5) ?
C6 H6 0.9500 ?
C7 C8 1.501(16) ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C8A H8AA 0.9800 ?
C8A H8AB 0.9800 ?
C8A H8AC 0.9800 ?
C9 C10 1.389(5) ?
C9 C14 1.403(4) ?
C10 C11 1.381(5) ?
C10 H10 0.9500 ?
C11 C12 1.381(5) ?
C12 C13 1.386(5) ?
C13 C14 1.387(5) ?
C13 H13 0.9500 ?
C16 C17 1.389(6) ?
C16 C21 1.392(5) ?
C17 C18 1.393(5) ?
C17 C22A 1.54(3) ?
C18 C19 1.375(7) ?
C18 H18 0.9500 ?
C19 C20 1.368(7) ?
C19 H19 0.9500 ?
C20 C21 1.393(6) ?
C20 H20 0.9500 ?
C21 C22 1.53(2) ?
C22 H22A 0.9800 ?
C22 H22B 0.9800 ?
C22 H22C 0.9800 ?
C22A H22D 0.9800 ?
C22A H22E 0.9800 ?
C22A H22F 0.9800 ?
C23 C24 1.460(6) ?
C24 H24A 0.9800 ?
C24 H24B 0.9800 ?
C24 H24C 0.9800 ?
C25 C26 1.455(6) ?
C26 H26A 0.9800 ?
C26 H26B 0.9800 ?
C26 H26C 0.9800 ?
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
N1 H1 Cl2 0.88 2.23 3.110(3) 173.3 3_656 yes
N2 H2 N5 0.88 2.17 2.979(4) 152.2 3_666 yes
N3 H3 N6 0.88 2.29 3.034(5) 142.0 . yes
N4 H4 Cl1 0.88 2.34 3.213(3) 169.3 3_656 yes
