#------------------------------------------------------------------------------
#$Date: 2019-11-17 04:54:18 +0200 (Sun, 17 Nov 2019) $
#$Revision: 227977 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/94/1549488.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_1549488
loop_
_publ_author_name
'Eremin, Dmitry B.'
'Boiko, Daniil A.'
'Borkovskaya, Eugenia V.'
'Khrustalev, Victor N.'
'Chernyshev, Victor M.'
'Ananikov, Valentine P.'
_publ_section_title
;
 Ten-fold boost of catalytic performance in thiol--yne click reaction
 enabled by a palladium diketonate complex with a
 hexafluoroacetylacetonate ligand
;
_journal_issue                   12
_journal_name_full               'Catalysis Science & Technology'
_journal_page_first              3073
_journal_paper_doi               10.1039/C8CY00173A
_journal_volume                  8
_journal_year                    2018
_chemical_formula_moiety         'C14 H18 O6 Pd, C H2 Cl2'
_chemical_formula_sum            'C15 H20 Cl2 O6 Pd'
_chemical_formula_weight         473.61
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-10-14 deposited with the CCDC.
2018-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.2230(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.6869(5)
_cell_length_b                   8.8935(4)
_cell_length_c                   8.5510(4)
_cell_measurement_reflns_used    6469
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.63
_cell_measurement_theta_min      2.38
_cell_volume                     888.76(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.639
_diffrn_reflns_theta_min         2.382
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.372
_exptl_absorpt_correction_T_max  0.777
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2003)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.770
_exptl_crystal_description       prism
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_refine_diff_density_max         1.607
_refine_diff_density_min         -1.416
_refine_diff_density_rms         0.089
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     68
_refine_ls_number_reflns         1717
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0217
_refine_ls_R_factor_gt           0.0217
_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)+(0.0234P)²+2.0123P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0555
_refine_ls_wR_factor_ref         0.0555
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1712
_reflns_number_total             1717
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cy00173a2.cif
_cod_data_source_block           Pdacpd2
_cod_depositor_comments
'Adding full bibliography for 1549488--1549489.cif.'
_cod_database_code               1549488
_shelx_shelxl_version_number     2014/7
_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   0.684
_shelx_estimated_absorpt_t_max   0.771
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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_adp
_atom_site_refinement_flags_occupancy
Pd1 Pd 0.5000 0.5000 0.0000 0.01225(6) Uani 1 4 d S T P
O1 O 0.40620(8) 0.33721(11) 0.09003(12) 0.01676(18) Uani 1 1 d . . .
O2 O 0.16994(15) 0.5000 0.4521(2) 0.0325(4) Uani 1 2 d S T P
C1 C 0.31601(11) 0.35934(15) 0.17149(15) 0.0149(2) Uani 1 1 d . . .
C2 C 0.26872(15) 0.5000 0.2102(2) 0.0147(3) Uani 1 2 d S T P
C3 C 0.26097(12) 0.21724(16) 0.22888(18) 0.0205(2) Uani 1 1 d . . .
H3A H 0.2849 0.1328 0.1630 0.031 Uiso 1 1 calc R U .
H3B H 0.1776 0.2277 0.2239 0.031 Uiso 1 1 calc R U .
H3C H 0.2845 0.1985 0.3373 0.031 Uiso 1 1 calc R U .
C4 C 0.16192(16) 0.5000 0.3109(2) 0.0178(3) Uani 1 2 d S T P
C5 C 0.04800(18) 0.5000 0.2293(3) 0.0252(4) Uani 1 2 d S T P
H5A H -0.0120 0.5000 0.3056 0.038 Uiso 1 2 d R U P
H5B H 0.0416 0.5881 0.1651 0.038 Uiso 1 1 d R U .
Cl1 Cl 0.5000 0.66659(8) 0.5000 0.03440(13) Uani 1 2 d S T P
C6 C 0.5543(3) 0.5000 0.4329(5) 0.0198(7) Uani 0.5 2 d S T P
H6A H 0.6349 0.5000 0.4549 0.024 Uiso 0.5 2 d R U P
H6B H 0.5459 0.5000 0.3212 0.024 Uiso 0.5 2 d R U 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'
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'
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
O1 Pd1 O1 94.34(6) . 6_565
O1 Pd1 O1 85.66(6) . 2_655
C1 O1 Pd1 123.97(9) . .
O1 C1 C2 126.09(13) . .
O1 C1 C3 113.77(12) . .
C2 C1 C3 120.14(12) . .
C1 C2 C1 125.44(16) . 6_565
C1 C2 C4 117.22(8) . .
C1 C3 H3A 109.5 . .
C1 C3 H3B 109.5 . .
H3A C3 H3B 109.5 . .
C1 C3 H3C 109.5 . .
H3A C3 H3C 109.5 . .
H3B C3 H3C 109.5 . .
O2 C4 C5 121.91(19) . .
O2 C4 C2 120.33(18) . .
C5 C4 C2 117.76(18) . .
C4 C5 H5A 109.5 . .
C4 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
Cl1 C6 Cl1 119.9(2) 5_666 .
Cl1 C6 H6A 107.4 . .
Cl1 C6 H6B 107.3 . .
H6A C6 H6B 106.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Pd1 O1 1.9741(10)
O1 C1 1.2808(15)
O2 C4 1.211(3)
C1 C2 1.4076(15)
C1 C3 1.5014(19)
C2 C4 1.519(3)
C3 H3A 0.9800
C3 H3B 0.9800
C3 H3C 0.9800
C4 C5 1.501(3)
C5 H5A 0.9599
C5 H5B 0.9601
Cl1 C6 1.712(2)
C6 H6A 0.9600
C6 H6B 0.9600
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_4
Pd1 O1 C1 C2 0.1(2) .
Pd1 O1 C1 C3 -179.04(9) .
O1 C1 C2 C1 -3.1(3) 6_565
C3 C1 C2 C1 175.99(13) 6_565
O1 C1 C2 C4 -178.96(14) .
C3 C1 C2 C4 0.2(2) .
C1 C2 C4 O2 88.09(14) .
C1 C2 C4 C5 -91.91(14) .
