#------------------------------------------------------------------------------
#$Date: 2015-12-09 16:57:49 +0200 (Wed, 09 Dec 2015) $
#$Revision: 171255 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/69/7036933.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_7036933
loop_
_publ_author_name
'Kumar, Kamlesh'
'Darkwa, James'
_publ_section_title
;
 Effect of chalcogens on CO insertion into the palladium-methyl bond of
 [(NNX)Pd(CH3)](+) (X = O, S, Se) and on CO/ethylene copolymerisation.
;
_journal_issue                   47
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              20714
_journal_page_last               20727
_journal_paper_doi               10.1039/c5dt03929k
_journal_volume                  44
_journal_year                    2015
_chemical_formula_moiety         '2(C19 H22 Cl N3 O Pd), C H2 Cl2'
_chemical_formula_sum            'C39 H46 Cl4 N6 O2 Pd2'
_chemical_formula_weight         985.42
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-06-22
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2014.11.03 svn.r3071 for OlexSys, GUI svn.r4932)
;
_audit_update_record
;
2015-09-30 deposited with the CCDC.
2015-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                94.752(2)
_cell_angle_beta                 97.174(2)
_cell_angle_gamma                111.388(2)
_cell_formula_units_Z            1
_cell_length_a                   8.9985(7)
_cell_length_b                   9.7348(8)
_cell_length_c                   12.7904(10)
_cell_measurement_reflns_used    6386
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.47
_cell_volume                     1025.05(14)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            14648
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         2.269
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0475 before and 0.0376 after correction.
The Ratio of minimum to maximum transmission is 0.9065.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.596
_exptl_crystal_description       blocks
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.412
_exptl_crystal_size_mid          0.361
_exptl_crystal_size_min          0.213
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.323
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         5045
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0239
_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)+(0.0226P)²+0.4289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0521
_refine_ls_wR_factor_ref         0.0541
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4553
_reflns_number_total             5045
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt03929k2.cif
_cod_data_source_block           15lm_kumar_kks_99
_cod_depositor_comments
'Adding full bibliography for 7036928--7036933.cif.'
_cod_database_code               7036933
_shelxl_version_number           2014/6
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C20(0.5) H20A(0.5) H20B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C6(H6A,H6B), C20(H20A,H20B)
3.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C3(H3), C2(H2), C4(H4), C8(H8), C12(H12), C11(H11), C10(H10), C9(H9)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C18(H18A,H18B,H18C), C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_occupancy
Pd1 Pd 0.22967(2) 0.22628(2) 0.67748(2) 0.01166(5) Uani 1 1 d . .
Cl1 Cl 0.04032(6) 0.33718(5) 0.67797(4) 0.01773(10) Uani 1 1 d . .
O1 O -0.14189(16) 0.01986(15) 0.91406(10) 0.0174(3) Uani 1 1 d . .
N1 N 0.06162(18) -0.00272(17) 0.69139(12) 0.0125(3) Uani 1 1 d . .
C19 C 0.3876(2) 0.4224(2) 0.64720(16) 0.0191(4) Uani 1 1 d . .
H19A H 0.3389 0.4537 0.5874 0.029 Uiso 1 1 calc GR .
H19B H 0.4840 0.4102 0.6314 0.029 Uiso 1 1 calc GR .
H19C H 0.4148 0.4964 0.7084 0.029 Uiso 1 1 calc GR .
N2 N 0.34581(18) -0.00230(17) 0.60543(12) 0.0130(3) Uani 1 1 d . .
C15 C 0.5872(2) 0.0343(2) 0.68945(16) 0.0187(4) Uani 1 1 d . .
H15 H 0.6840 0.0237 0.7126 0.022 Uiso 1 1 calc R .
N3 N 0.39578(18) 0.13064(17) 0.67052(12) 0.0137(3) Uani 1 1 d . .
C3 C -0.1572(2) -0.2952(2) 0.67580(16) 0.0209(4) Uani 1 1 d . .
H3 H -0.2328 -0.3922 0.6695 0.025 Uiso 1 1 calc R .
C2 C -0.0491(2) -0.2559(2) 0.60437(15) 0.0171(4) Uani 1 1 d . .
H2 H -0.0491 -0.3265 0.5507 0.021 Uiso 1 1 calc R .
C5 C -0.0387(2) -0.0433(2) 0.76309(14) 0.0133(4) Uani 1 1 d . .
C18 C 0.4316(3) -0.2130(2) 0.55905(17) 0.0219(4) Uani 1 1 d . .
H18A H 0.3460 -0.2884 0.5839 0.033 Uiso 1 1 calc GR .
H18B H 0.5293 -0.2320 0.5723 0.033 Uiso 1 1 calc GR .
H18C H 0.4026 -0.2143 0.4840 0.033 Uiso 1 1 calc GR .
C13 C 0.1837(2) -0.0613(2) 0.54266(14) 0.0141(4) Uani 1 1 d . .
H13A H 0.1719 -0.1456 0.4917 0.017 Uiso 1 1 calc R .
H13B H 0.1673 0.0146 0.5035 0.017 Uiso 1 1 calc R .
C17 C 0.6368(2) 0.2877(2) 0.80254(17) 0.0232(4) Uani 1 1 d . .
H17A H 0.6542 0.2571 0.8709 0.035 Uiso 1 1 calc GR .
H17B H 0.5768 0.3513 0.8063 0.035 Uiso 1 1 calc GR .
H17C H 0.7393 0.3410 0.7822 0.035 Uiso 1 1 calc GR .
C4 C -0.1510(2) -0.1878(2) 0.75664(15) 0.0182(4) Uani 1 1 d . .
H4 H -0.2210 -0.2123 0.8058 0.022 Uiso 1 1 calc R .
C1 C 0.0585(2) -0.1095(2) 0.61495(14) 0.0133(4) Uani 1 1 d . .
C8 C -0.2823(2) 0.0618(2) 1.04766(15) 0.0186(4) Uani 1 1 d . .
H8 H -0.3519 -0.0376 1.0307 0.022 Uiso 1 1 calc R .
C7 C -0.1543(2) 0.1199(2) 0.99236(14) 0.0154(4) Uani 1 1 d . .
C12 C -0.0502(2) 0.2688(2) 1.01706(15) 0.0186(4) Uani 1 1 d . .
H12 H 0.0350 0.3079 0.9800 0.022 Uiso 1 1 calc R .
C6 C -0.0196(2) 0.0784(2) 0.85055(14) 0.0151(4) Uani 1 1 d . .
H6A H 0.0869 0.1115 0.8939 0.018 Uiso 1 1 calc R .
H6B H -0.0311 0.1629 0.8204 0.018 Uiso 1 1 calc R .
C14 C 0.4581(2) -0.0642(2) 0.61630(15) 0.0160(4) Uani 1 1 d . .
C11 C -0.0755(3) 0.3577(2) 1.09786(16) 0.0228(4) Uani 1 1 d . .
H11 H -0.0062 0.4572 1.1148 0.027 Uiso 1 1 calc R .
C16 C 0.5435(2) 0.1536(2) 0.72204(15) 0.0165(4) Uani 1 1 d . .
C10 C -0.2018(3) 0.3015(2) 1.15389(16) 0.0246(5) Uani 1 1 d . .
H10 H -0.2171 0.3624 1.2080 0.029 Uiso 1 1 calc R .
C9 C -0.3055(3) 0.1526(2) 1.12806(16) 0.0233(4) Uani 1 1 d . .
H9 H -0.3908 0.1138 1.1650 0.028 Uiso 1 1 calc R .
Cl2 Cl -0.41776(8) -0.36262(7) 0.95845(5) 0.03752(15) Uani 1 1 d . .
C20 C -0.6051(5) -0.5107(5) 0.9519(3) 0.0243(9) Uani 0.5 1 d . P
H20A H -0.6428 -0.5627 0.8798 0.029 Uiso 0.5 1 calc R P
H20B H -0.6848 -0.4722 0.9713 0.029 Uiso 0.5 1 calc R P
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'
O O 0.0106 0.0060 '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
N1 Pd1 Cl1 96.59(4) . .
C19 Pd1 Cl1 87.39(6) . .
C19 Pd1 N1 172.56(7) . .
C19 Pd1 N3 91.46(7) . .
N3 Pd1 Cl1 177.58(4) . .
N3 Pd1 N1 84.33(6) . .
C7 O1 C6 116.49(15) . .
C5 N1 Pd1 127.41(13) . .
C5 N1 C1 118.29(16) . .
C1 N1 Pd1 114.24(12) . .
Pd1 C19 H19A 109.5 . .
Pd1 C19 H19B 109.5 . .
Pd1 C19 H19C 109.5 . .
H19A C19 H19B 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
N3 N2 C13 118.85(15) . .
C14 N2 N3 111.37(15) . .
C14 N2 C13 129.62(16) . .
C14 C15 H15 126.7 . .
C14 C15 C16 106.66(17) . .
C16 C15 H15 126.7 . .
N2 N3 Pd1 116.34(11) . .
C16 N3 Pd1 137.06(14) . .
C16 N3 N2 106.16(15) . .
C2 C3 H3 120.4 . .
C4 C3 H3 120.4 . .
C4 C3 C2 119.15(18) . .
C3 C2 H2 120.7 . .
C1 C2 C3 118.55(18) . .
C1 C2 H2 120.7 . .
N1 C5 C4 122.03(18) . .
N1 C5 C6 115.40(16) . .
C4 C5 C6 122.57(17) . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C14 C18 H18A 109.5 . .
C14 C18 H18B 109.5 . .
C14 C18 H18C 109.5 . .
N2 C13 H13A 109.7 . .
N2 C13 H13B 109.7 . .
N2 C13 C1 109.97(15) . .
H13A C13 H13B 108.2 . .
C1 C13 H13A 109.7 . .
C1 C13 H13B 109.7 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C16 C17 H17A 109.5 . .
C16 C17 H17B 109.5 . .
C16 C17 H17C 109.5 . .
C3 C4 C5 119.18(18) . .
C3 C4 H4 120.4 . .
C5 C4 H4 120.4 . .
N1 C1 C2 122.67(17) . .
N1 C1 C13 116.25(16) . .
C2 C1 C13 121.05(17) . .
C7 C8 H8 120.1 . .
C9 C8 H8 120.1 . .
C9 C8 C7 119.76(19) . .
O1 C7 C8 115.07(17) . .
O1 C7 C12 124.53(18) . .
C12 C7 C8 120.39(18) . .
C7 C12 H12 120.5 . .
C11 C12 C7 118.91(19) . .
C11 C12 H12 120.5 . .
O1 C6 C5 108.02(15) . .
O1 C6 H6A 110.1 . .
O1 C6 H6B 110.1 . .
C5 C6 H6A 110.1 . .
C5 C6 H6B 110.1 . .
H6A C6 H6B 108.4 . .
N2 C14 C15 106.29(17) . .
N2 C14 C18 122.70(17) . .
C15 C14 C18 130.98(18) . .
C12 C11 H11 119.3 . .
C10 C11 C12 121.4(2) . .
C10 C11 H11 119.3 . .
C15 C16 C17 128.67(18) . .
N3 C16 C15 109.51(17) . .
N3 C16 C17 121.81(18) . .
C11 C10 H10 120.5 . .
C11 C10 C9 119.1(2) . .
C9 C10 H10 120.5 . .
C8 C9 C10 120.4(2) . .
C8 C9 H9 119.8 . .
C10 C9 H9 119.8 . .
C20 Cl2 C20 70.5(2) . 2_447
Cl2 C20 Cl2 109.5(2) . 2_447
Cl2 C20 H20A 109.8 . .
Cl2 C20 H20A 109.8 2_447 .
Cl2 C20 H20B 109.8 . .
Cl2 C20 H20B 109.8 2_447 .
H20A C20 H20B 108.2 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 Cl1 2.3264(5) .
Pd1 N1 2.2276(16) .
Pd1 C19 2.0238(19) .
Pd1 N3 2.0355(16) .
O1 C7 1.382(2) .
O1 C6 1.428(2) .
N1 C5 1.348(2) .
N1 C1 1.357(2) .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
N2 N3 1.369(2) .
N2 C13 1.456(2) .
N2 C14 1.352(2) .
C15 H15 0.9300 .
C15 C14 1.382(3) .
C15 C16 1.403(3) .
N3 C16 1.339(2) .
C3 H3 0.9300 .
C3 C2 1.392(3) .
C3 C4 1.389(3) .
C2 H2 0.9300 .
C2 C1 1.384(3) .
C5 C4 1.390(3) .
C5 C6 1.506(3) .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C18 C14 1.489(3) .
C13 H13A 0.9700 .
C13 H13B 0.9700 .
C13 C1 1.514(3) .
C17 H17A 0.9600 .
C17 H17B 0.9600 .
C17 H17C 0.9600 .
C17 C16 1.494(3) .
C4 H4 0.9300 .
C8 H8 0.9300 .
C8 C7 1.393(3) .
C8 C9 1.386(3) .
C7 C12 1.392(3) .
C12 H12 0.9300 .
C12 C11 1.387(3) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C11 H11 0.9300 .
C11 C10 1.386(3) .
C10 H10 0.9300 .
C10 C9 1.392(3) .
C9 H9 0.9300 .
Cl2 C20 1.761(4) .
Cl2 C20 1.800(4) 2_447
C20 Cl2 1.800(4) 2_447
C20 H20A 0.9700 .
C20 H20B 0.9700 .
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
Pd1 N1 C5 C4 172.79(13) . .
Pd1 N1 C5 C6 -7.6(2) . .
Pd1 N1 C1 C2 -173.80(14) . .
Pd1 N1 C1 C13 8.02(19) . .
Pd1 N3 C16 C15 171.59(14) . .
Pd1 N3 C16 C17 -7.2(3) . .
O1 C7 C12 C11 -179.81(17) . .
N1 C5 C4 C3 1.9(3) . .
N1 C5 C6 O1 175.73(15) . .
N2 N3 C16 C15 -0.1(2) . .
N2 N3 C16 C17 -178.84(17) . .
N2 C13 C1 N1 58.7(2) . .
N2 C13 C1 C2 -119.51(19) . .
N3 N2 C13 C1 -69.3(2) . .
N3 N2 C14 C15 -1.4(2) . .
N3 N2 C14 C18 176.74(17) . .
C3 C2 C1 N1 -0.7(3) . .
C3 C2 C1 C13 177.43(17) . .
C2 C3 C4 C5 1.1(3) . .
C5 N1 C1 C2 3.6(3) . .
C5 N1 C1 C13 -174.60(15) . .
C13 N2 N3 Pd1 3.1(2) . .
C13 N2 N3 C16 176.79(15) . .
C13 N2 C14 C15 -176.70(17) . .
C13 N2 C14 C18 1.5(3) . .
C4 C3 C2 C1 -1.7(3) . .
C4 C5 C6 O1 -4.7(2) . .
C1 N1 C5 C4 -4.2(3) . .
C1 N1 C5 C6 175.40(15) . .
C8 C7 C12 C11 0.3(3) . .
C7 O1 C6 C5 -173.63(15) . .
C7 C8 C9 C10 0.0(3) . .
C7 C12 C11 C10 -0.1(3) . .
C12 C11 C10 C9 -0.2(3) . .
C6 O1 C7 C8 175.46(16) . .
C6 O1 C7 C12 -4.4(3) . .
C6 C5 C4 C3 -177.64(18) . .
C14 N2 N3 Pd1 -172.74(12) . .
C14 N2 N3 C16 0.9(2) . .
C14 N2 C13 C1 105.7(2) . .
C14 C15 C16 N3 -0.8(2) . .
C14 C15 C16 C17 177.88(19) . .
C11 C10 C9 C8 0.2(3) . .
C16 C15 C14 N2 1.3(2) . .
C16 C15 C14 C18 -176.6(2) . .
C9 C8 C7 O1 179.83(17) . .
C9 C8 C7 C12 -0.3(3) . .
C20 Cl2 C20 Cl2 0.000(0) 2_447 2_447
