#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:44:06 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178579 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/89/4068934.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_4068934
loop_
_publ_author_name
'Zhang, Xiaoqin'
'Qiu, Yuping'
'Rao, Bin'
'Luo, Meiming'
_publ_section_title
;
 Palladium(II)−N-Heterocyclic Carbene Metallacrown Ether Complexes:
 Synthesis, Structure, and Catalytic Activity in the Suzuki−Miyaura
 Reaction
;
_journal_issue                   10
_journal_name_full               Organometallics
_journal_page_first              3093
_journal_paper_doi               10.1021/om8011695
_journal_volume                  28
_journal_year                    2009
_chemical_formula_sum            'C56 H72 Ag2 Cl2 N6 O6'
_chemical_formula_weight         1211.84
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                91.62(3)
_cell_angle_beta                 109.31(2)
_cell_angle_gamma                95.46(2)
_cell_formula_units_Z            1
_cell_length_a                   9.502(3)
_cell_length_b                   12.470(2)
_cell_length_c                   13.462(4)
_cell_measurement_reflns_used    23
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      7.56
_cell_measurement_theta_min      4.53
_cell_volume                     1495.5(7)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       Omega/2_theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0040
_diffrn_reflns_av_sigmaI/netI    0.0501
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5525
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.61
_diffrn_standards_decay_%        1.043
_diffrn_standards_interval_count 300
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_T_max  0.8573
_exptl_absorpt_correction_T_min  0.6737
_exptl_absorpt_correction_type   sphere
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             626
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.993
_refine_diff_density_min         -0.689
_refine_diff_density_rms         0.085
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     334
_refine_ls_number_reflns         5469
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.1038
_refine_ls_R_factor_gt           0.0548
_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)+(0.0800P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1453
_reflns_number_gt                3333
_reflns_number_total             5469
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om8011695_si_002.cif
_cod_data_source_block           cd4
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1495.4(7)
_cod_database_code               4068934
loop_
_symmetry_equiv_pos_as_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_calc_flag
_atom_site_refinement_flags
Ag1 Ag 0.65249(4) 0.48340(3) 0.61688(3) 0.0711(2) Uani 1 d .
Cl1 Cl 0.59810(17) 0.65139(11) 0.54399(10) 0.0767(4) Uani 1 d .
O1 O 0.5226(4) 0.2476(3) 0.9158(3) 0.0823(11) Uani 1 d .
O2 O 0.6390(6) 0.1198(4) 1.0604(3) 0.1036(13) Uani 1 d .
O3 O 0.8908(9) 0.0095(7) 1.0776(7) 0.187(3) Uani 1 d .
N1 N 0.8833(4) 0.3406(3) 0.7500(3) 0.0590(10) Uani 1 d .
N2 N 0.6694(4) 0.2892(3) 0.7613(3) 0.0624(10) Uani 1 d .
C1 C 1.0326(6) 0.3370(4) 0.6346(4) 0.0674(13) Uani 1 d .
C2 C 1.1441(7) 0.3889(5) 0.6010(4) 0.0809(17) Uani 1 d .
H2 H 1.1706 0.3553 0.5482 0.097 Uiso 1 calc R
C3 C 1.2150(7) 0.4880(5) 0.6440(5) 0.0896(18) Uani 1 d .
H3 H 1.2903 0.5199 0.6210 0.107 Uiso 1 calc R
C4 C 1.1777(7) 0.5420(5) 0.7209(5) 0.0849(17) Uani 1 d .
H4 H 1.2269 0.6098 0.7487 0.102 Uiso 1 calc R
C5 C 1.0663(6) 0.4951(5) 0.7566(4) 0.0699(14) Uani 1 d .
C6 C 0.9970(5) 0.3928(4) 0.7127(4) 0.0602(12) Uani 1 d .
C7 C 0.9553(7) 0.2275(5) 0.5849(4) 0.0826(16) Uani 1 d .
H7 H 0.8873 0.2024 0.6226 0.099 Uiso 1 calc R
C8 C 1.0260(7) 0.5569(5) 0.8408(5) 0.0864(17) Uani 1 d .
H8 H 0.9319 0.5200 0.8439 0.104 Uiso 1 calc R
C9 C 1.0660(11) 0.1457(6) 0.5955(8) 0.160(4) Uani 1 d .
H9A H 1.0129 0.0746 0.5773 0.239 Uiso 1 calc R
H9B H 1.1334 0.1494 0.6670 0.239 Uiso 1 calc R
H9C H 1.1222 0.1610 0.5490 0.239 Uiso 1 calc R
C10 C 0.8644(13) 0.2297(8) 0.4717(6) 0.172(4) Uani 1 d .
H10A H 0.7742 0.2617 0.4656 0.259 Uiso 1 calc R
H10B H 0.8390 0.1573 0.4402 0.259 Uiso 1 calc R
H10C H 0.9212 0.2714 0.4363 0.259 Uiso 1 calc R
C11 C 0.9975(9) 0.6714(5) 0.8132(6) 0.118(2) Uani 1 d .
H11A H 1.0903 0.7128 0.8180 0.177 Uiso 1 calc R
H11B H 0.9559 0.7033 0.8614 0.177 Uiso 1 calc R
H11C H 0.9282 0.6709 0.7426 0.177 Uiso 1 calc R
C12 C 1.1453(8) 0.5517(6) 0.9496(5) 0.116(2) Uani 1 d .
H12A H 1.1593 0.4776 0.9636 0.175 Uiso 1 calc R
H12B H 1.1129 0.5840 1.0027 0.175 Uiso 1 calc R
H12C H 1.2383 0.5900 0.9506 0.175 Uiso 1 calc R
C13 C 0.7379(5) 0.3603(4) 0.7137(4) 0.0601(12) Uani 1 d .
C14 C 0.9035(7) 0.2589(4) 0.8198(4) 0.0740(15) Uani 1 d .
H14 H 0.9933 0.2316 0.8547 0.089 Uiso 1 calc R
C15 C 0.7706(6) 0.2274(4) 0.8269(4) 0.0751(15) Uani 1 d .
H15 H 0.7492 0.1739 0.8682 0.090 Uiso 1 calc R
C16 C 0.5075(6) 0.2776(5) 0.7416(4) 0.0728(14) Uani 1 d .
H16A H 0.4688 0.2021 0.7251 0.087 Uiso 1 calc R
H16B H 0.4590 0.3171 0.6808 0.087 Uiso 1 calc R
C17 C 0.4685(6) 0.3183(4) 0.8339(4) 0.0739(14) Uani 1 d .
H17A H 0.5155 0.3914 0.8566 0.089 Uiso 1 calc R
H17B H 0.3608 0.3182 0.8150 0.089 Uiso 1 calc R
C18 C 0.4958(7) 0.2649(4) 1.0085(5) 0.0791(16) Uani 1 d .
C19 C 0.4187(8) 0.3442(5) 1.0279(5) 0.099(2) Uani 1 d .
H19 H 0.3798 0.3922 0.9769 0.119 Uiso 1 calc R
C20 C 0.3985(9) 0.3527(6) 1.1269(7) 0.116(3) Uani 1 d .
H20 H 0.3467 0.4073 1.1414 0.140 Uiso 1 calc R
C21 C 0.4523(10) 0.2841(8) 1.1992(7) 0.126(3) Uani 1 d .
H21 H 0.4332 0.2889 1.2625 0.151 Uiso 1 calc R
C22 C 0.5354(9) 0.2060(6) 1.1829(5) 0.109(2) Uani 1 d .
H22 H 0.5751 0.1597 1.2355 0.131 Uiso 1 calc R
C23 C 0.5603(8) 0.1964(5) 1.0861(5) 0.0906(18) Uani 1 d .
C24 C 0.6925(10) 0.0396(7) 1.1316(6) 0.128(3) Uani 1 d .
H24A H 0.6105 0.0038 1.1504 0.153 Uiso 1 calc R
H24B H 0.7678 0.0728 1.1955 0.153 Uiso 1 calc R
C25 C 0.7567(11) -0.0384(7) 1.0833(8) 0.140(3) Uani 1 d .
H25A H 0.7740 -0.1011 1.1250 0.168 Uiso 1 calc R
H25B H 0.6885 -0.0618 1.0131 0.168 Uiso 1 calc R
C26 C 0.9238(14) -0.0225(12) 0.9997(10) 0.195(5) Uani 1 d .
H26A H 0.8493 -0.0031 0.9358 0.233 Uiso 1 calc R
H26B H 0.9187 -0.1006 0.9975 0.233 Uiso 1 calc R
N3 N 0.504(3) -0.0058(13) 0.3530(19) 0.322(13) Uani 1 d .
C27 C 0.390(4) 0.0298(15) 0.3586(17) 0.262(13) Uani 1 d .
C28 C 0.284(3) 0.0670(12) 0.3851(19) 0.41(2) Uani 1 d .
H28A H 0.1924 0.0566 0.3263 0.26(4) Uiso 1 calc R
H28B H 0.3104 0.1427 0.4052 0.26(4) Uiso 1 calc R
H28C H 0.2717 0.0295 0.4434 0.26(4) Uiso 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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 '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
C13 Ag1 Cl1 165.34(14) . .
C18 O1 C17 118.5(4) . .
C23 O2 C24 119.6(5) . .
C26 O3 C25 115.2(10) . .
C13 N1 C14 111.0(4) . .
C13 N1 C6 123.2(4) . .
C14 N1 C6 125.7(4) . .
C13 N2 C15 111.3(4) . .
C13 N2 C16 123.3(4) . .
C15 N2 C16 125.3(4) . .
C6 C1 C2 116.3(5) . .
C6 C1 C7 123.6(5) . .
C2 C1 C7 120.1(5) . .
C3 C2 C1 121.3(5) . .
C3 C2 H2 119.4 . .
C1 C2 H2 119.4 . .
C2 C3 C4 121.5(5) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C3 C4 C5 119.9(6) . .
C3 C4 H4 120.1 . .
C5 C4 H4 120.1 . .
C4 C5 C6 117.6(5) . .
C4 C5 C8 118.9(5) . .
C6 C5 C8 123.5(4) . .
C1 C6 C5 123.4(4) . .
C1 C6 N1 117.6(5) . .
C5 C6 N1 119.0(4) . .
C10 C7 C9 108.6(7) . .
C10 C7 C1 113.2(5) . .
C9 C7 C1 111.7(6) . .
C10 C7 H7 107.7 . .
C9 C7 H7 107.7 . .
C1 C7 H7 107.7 . .
C11 C8 C5 112.3(5) . .
C11 C8 C12 112.6(6) . .
C5 C8 C12 110.5(5) . .
C11 C8 H8 107.0 . .
C5 C8 H8 107.0 . .
C12 C8 H8 107.0 . .
C7 C9 H9A 109.5 . .
C7 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C7 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C7 C10 H10A 109.5 . .
C7 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C7 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
N2 C13 N1 103.9(4) . .
N2 C13 Ag1 130.0(4) . .
N1 C13 Ag1 125.9(3) . .
C15 C14 N1 106.9(5) . .
C15 C14 H14 126.6 . .
N1 C14 H14 126.6 . .
C14 C15 N2 106.9(4) . .
C14 C15 H15 126.5 . .
N2 C15 H15 126.5 . .
N2 C16 C17 112.6(4) . .
N2 C16 H16A 109.1 . .
C17 C16 H16A 109.1 . .
N2 C16 H16B 109.1 . .
C17 C16 H16B 109.1 . .
H16A C16 H16B 107.8 . .
O1 C17 C16 106.8(4) . .
O1 C17 H17A 110.4 . .
C16 C17 H17A 110.4 . .
O1 C17 H17B 110.4 . .
C16 C17 H17B 110.4 . .
H17A C17 H17B 108.6 . .
C19 C18 O1 124.6(5) . .
C19 C18 C23 120.8(5) . .
O1 C18 C23 114.6(5) . .
C18 C19 C20 118.8(7) . .
C18 C19 H19 120.6 . .
C20 C19 H19 120.6 . .
C21 C20 C19 120.8(7) . .
C21 C20 H20 119.6 . .
C19 C20 H20 119.6 . .
C20 C21 C22 121.4(7) . .
C20 C21 H21 119.3 . .
C22 C21 H21 119.3 . .
C21 C22 C23 119.4(7) . .
C21 C22 H22 120.3 . .
C23 C22 H22 120.3 . .
O2 C23 C18 116.9(5) . .
O2 C23 C22 124.4(7) . .
C18 C23 C22 118.7(7) . .
O2 C24 C25 109.7(6) . .
O2 C24 H24A 109.7 . .
C25 C24 H24A 109.7 . .
O2 C24 H24B 109.7 . .
C25 C24 H24B 109.7 . .
H24A C24 H24B 108.2 . .
O3 C25 C24 108.4(9) . .
O3 C25 H25A 110.0 . .
C24 C25 H25A 110.0 . .
O3 C25 H25B 110.0 . .
C24 C25 H25B 110.0 . .
H25A C25 H25B 108.4 . .
O3 C26 C26 114.4(18) . 2_757
O3 C26 H26A 108.7 . .
C26 C26 H26A 108.7 2_757 .
O3 C26 H26B 108.7 . .
C26 C26 H26B 108.7 2_757 .
H26A C26 H26B 107.6 . .
C28 C27 N3 168(3) . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Ag1 C13 2.089(5) .
Ag1 Cl1 2.3675(15) .
O1 C18 1.369(6) .
O1 C17 1.423(6) .
O2 C23 1.370(7) .
O2 C24 1.417(8) .
O3 C26 1.255(13) .
O3 C25 1.382(10) .
N1 C13 1.354(6) .
N1 C14 1.389(6) .
N1 C6 1.444(6) .
N2 C13 1.348(6) .
N2 C15 1.385(6) .
N2 C16 1.464(6) .
C1 C6 1.394(6) .
C1 C2 1.396(7) .
C1 C7 1.512(8) .
C2 C3 1.364(8) .
C2 H2 0.9300 .
C3 C4 1.378(8) .
C3 H3 0.9300 .
C4 C5 1.389(7) .
C4 H4 0.9300 .
C5 C6 1.396(7) .
C5 C8 1.523(7) .
C7 C10 1.485(9) .
C7 C9 1.510(9) .
C7 H7 0.9800 .
C8 C11 1.512(9) .
C8 C12 1.536(9) .
C8 H8 0.9800 .
C9 H9A 0.9600 .
C9 H9B 0.9600 .
C9 H9C 0.9600 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C14 C15 1.321(7) .
C14 H14 0.9300 .
C15 H15 0.9300 .
C16 C17 1.497(7) .
C16 H16A 0.9700 .
C16 H16B 0.9700 .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 C19 1.354(8) .
C18 C23 1.387(8) .
C19 C20 1.410(9) .
C19 H19 0.9300 .
C20 C21 1.320(11) .
C20 H20 0.9300 .
C21 C22 1.367(10) .
C21 H21 0.9300 .
C22 C23 1.403(8) .
C22 H22 0.9300 .
C24 C25 1.442(11) .
C24 H24A 0.9700 .
C24 H24B 0.9700 .
C25 H25A 0.9700 .
C25 H25B 0.9700 .
C26 C26 1.50(2) 2_757
C26 H26A 0.9700 .
C26 H26B 0.9700 .
N3 C27 1.23(3) .
C27 C28 1.29(3) .
C28 H28A 0.9600 .
C28 H28B 0.9600 .
C28 H28C 0.9600 .
