#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:50:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178703 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/14/4081475.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_4081475
loop_
_publ_author_name
'Kinzhalov, Mikhail A.'
'Luzyanin, Konstantin V.'
'Boyarskiy, Vadim P.'
'Haukka, Matti'
'Kukushkin, Vadim Yu.'
_publ_section_title
;
 ADC-Based Palladium Catalysts for Aqueous Suzuki--Miyaura Cross-Coupling
 Exhibit Greater Activity than the Most Advantageous Catalytic Systems
;
_journal_issue                   18
_journal_name_full               Organometallics
_journal_page_first              5212
_journal_paper_doi               10.1021/om4007592
_journal_volume                  32
_journal_year                    2013
_chemical_formula_moiety         'C22 H20 Cl4 N4 O2 Pd S, C H2 Cl2'
_chemical_formula_sum            'C23 H22 Cl6 N4 O2 Pd S'
_chemical_formula_weight         737.61
_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                111.7470(10)
_cell_angle_beta                 102.344(2)
_cell_angle_gamma                95.338(2)
_cell_formula_units_Z            2
_cell_length_a                   11.6878(5)
_cell_length_b                   11.6902(4)
_cell_length_c                   11.7066(5)
_cell_measurement_reflns_used    9839
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      37.94
_cell_measurement_theta_min      2.28
_cell_volume                     1424.93(10)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 16
_diffrn_measured_fraction_theta_full 0.976
_diffrn_measured_fraction_theta_max 0.976
_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  0.0161
_diffrn_reflns_av_sigmaI/netI    0.0169
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            49706
_diffrn_reflns_theta_full        38.00
_diffrn_reflns_theta_max         38.00
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    1.317
_exptl_absorpt_correction_T_max  0.7759
_exptl_absorpt_correction_T_min  0.7217
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.719
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.654
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         15163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0199
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0168P)²+0.6880P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0495
_refine_ls_wR_factor_ref         0.0508
_reflns_number_gt                13916
_reflns_number_total             15163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4007592_si_003.cif
_cod_data_source_block           37
_cod_database_code               4081475
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.119954(5) 0.673954(6) 0.180296(6) 0.00978(1) Uani 1 1 d . . .
Cl1 Cl -0.012864(18) 0.77893(2) 0.28983(2) 0.01541(4) Uani 1 1 d . . .
Cl2 Cl 0.045504(18) 0.72198(2) 0.00719(2) 0.01445(3) Uani 1 1 d . . .
Cl3 Cl 0.44187(5) 0.75607(5) 0.34431(5) 0.01930(9) Uani 0.7156(16) 1 d P A 1
C8 C 0.3042(5) 0.7545(5) -0.1117(3) 0.0230(3) Uani 0.7156(16) 1 d P A 1
H8A H 0.3014 0.8126 -0.1544 0.034 Uiso 0.7156(16) 1 calc PR A 1
H8B H 0.2229 0.7122 -0.1254 0.034 Uiso 0.7156(16) 1 calc PR A 1
H8C H 0.3515 0.6919 -0.1470 0.034 Uiso 0.7156(16) 1 calc PR A 1
C8B C 0.4365(7) 0.7706(7) 0.3298(7) 0.01930(9) Uani 0.2844(16) 1 d P A 2
H8B1 H 0.3753 0.7867 0.3763 0.029 Uiso 0.2844(16) 1 calc PR A 2
H8B2 H 0.5157 0.8034 0.3904 0.029 Uiso 0.2844(16) 1 calc PR A 2
H8B3 H 0.4277 0.6800 0.2820 0.029 Uiso 0.2844(16) 1 calc PR A 2
Cl3B Cl 0.2939(3) 0.7365(3) -0.13856(17) 0.0230(3) Uani 0.2844(16) 1 d P A 2
Cl4 Cl 0.43432(3) 0.64073(3) 0.56101(3) 0.02604(5) Uani 1 1 d . . .
Cl5 Cl 0.26353(3) 0.01099(3) 0.44852(3) 0.02689(5) Uani 1 1 d . . .
Cl6 Cl 0.21728(3) -0.12299(3) 0.60657(3) 0.02973(6) Uani 1 1 d . . .
S1 S 0.340798(19) 0.30556(2) -0.03106(2) 0.01354(4) Uani 1 1 d . . .
O1 O 0.35391(7) 0.22517(7) -0.15223(8) 0.01971(13) Uani 1 1 d . . .
O2 O 0.44096(6) 0.39486(7) 0.06430(8) 0.02096(14) Uani 1 1 d . . .
N1 N 0.31918(7) 0.63470(7) 0.06155(7) 0.01306(12) Uani 1 1 d . . .
N2 N 0.19320(7) 0.45787(7) 0.02690(7) 0.01244(11) Uani 1 1 d . . .
N3 N 0.24215(7) 0.38778(7) -0.07074(7) 0.01283(11) Uani 1 1 d . . .
N4 N 0.19550(8) 0.56032(8) 0.37720(8) 0.01598(13) Uani 1 1 d . . .
C1 C 0.22502(7) 0.58274(8) 0.08212(8) 0.01111(12) Uani 1 1 d . . .
C2 C 0.36463(7) 0.76621(8) 0.11181(8) 0.01253(13) Uani 1 1 d . A .
C3 C 0.42271(8) 0.83254(9) 0.24103(9) 0.01461(14) Uani 1 1 d . . .
C4 C 0.47221(9) 0.95945(9) 0.28747(11) 0.01988(17) Uani 1 1 d . A .
H4 H 0.5102 1.0053 0.3758 0.024 Uiso 1 1 calc R . .
C5 C 0.46554(9) 1.01806(9) 0.20349(12) 0.02256(19) Uani 1 1 d . . .
H5 H 0.4995 1.1045 0.2345 0.027 Uiso 1 1 calc R A .
C6 C 0.40993(9) 0.95193(10) 0.07488(12) 0.02090(18) Uani 1 1 d . A .
H6 H 0.4060 0.9936 0.0186 0.025 Uiso 1 1 calc R . .
C7 C 0.35966(8) 0.82530(9) 0.02696(9) 0.01527(14) Uani 1 1 d . . .
C9 C 0.27441(8) 0.21585(9) 0.03739(9) 0.01536(14) Uani 1 1 d . . .
C10 C 0.29587(10) 0.26124(10) 0.16944(10) 0.02074(17) Uani 1 1 d . . .
H10 H 0.3463 0.3401 0.2230 0.025 Uiso 1 1 calc R . .
C11 C 0.24187(11) 0.18857(12) 0.22144(12) 0.0260(2) Uani 1 1 d . . .
H11 H 0.2554 0.2178 0.3114 0.031 Uiso 1 1 calc R . .
C12 C 0.16823(11) 0.07340(12) 0.14221(13) 0.0264(2) Uani 1 1 d . . .
H12 H 0.1321 0.0240 0.1784 0.032 Uiso 1 1 calc R . .
C13 C 0.14710(9) 0.02999(11) 0.01057(12) 0.02297(19) Uani 1 1 d . . .
H13 H 0.0965 -0.0488 -0.0429 0.028 Uiso 1 1 calc R . .
C14 C 0.19956(9) 0.10124(9) -0.04331(10) 0.01832(16) Uani 1 1 d . . .
H14 H 0.1848 0.0725 -0.1333 0.022 Uiso 1 1 calc R . .
C15 C 0.17158(8) 0.60910(9) 0.30792(8) 0.01446(14) Uani 1 1 d . . .
C16 C 0.21407(9) 0.49546(9) 0.45603(8) 0.01550(14) Uani 1 1 d . . .
C17 C 0.32334(9) 0.52443(9) 0.54673(9) 0.01759(15) Uani 1 1 d . . .
C18 C 0.34273(11) 0.45875(11) 0.62438(10) 0.02221(18) Uani 1 1 d . . .
H18 H 0.4168 0.4778 0.6865 0.027 Uiso 1 1 calc R . .
C19 C 0.25217(12) 0.36489(11) 0.60980(11) 0.0251(2) Uani 1 1 d . . .
H19 H 0.2648 0.3191 0.6622 0.030 Uiso 1 1 calc R . .
C20 C 0.14332(11) 0.33670(11) 0.51988(11) 0.02382(19) Uani 1 1 d . . .
H20 H 0.0824 0.2724 0.5123 0.029 Uiso 1 1 calc R . .
C21 C 0.12177(9) 0.40100(10) 0.44063(9) 0.01906(16) Uani 1 1 d . . .
C22 C 0.00381(10) 0.36865(12) 0.33923(11) 0.0245(2) Uani 1 1 d . . .
H22A H -0.0288 0.4450 0.3491 0.037 Uiso 1 1 calc R . .
H22B H -0.0527 0.3080 0.3492 0.037 Uiso 1 1 calc R . .
H22C H 0.0171 0.3322 0.2542 0.037 Uiso 1 1 calc R . .
C23 C 0.19272(11) 0.00552(11) 0.56551(11) 0.0259(2) Uani 1 1 d . . .
H23A H 0.1059 -0.0007 0.5332 0.031 Uiso 1 1 calc R . .
H23B H 0.2230 0.0844 0.6429 0.031 Uiso 1 1 calc R . .
H1N H 0.3548(15) 0.5847(16) 0.0138(16) 0.026(4) Uiso 1 1 d . . .
H2N H 0.1287(14) 0.4224(15) 0.0319(15) 0.019(4) Uiso 1 1 d . . .
H3N H 0.1876(15) 0.3442(16) -0.1341(16) 0.025(4) Uiso 1 1 d . . .
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'
S S 0.1246 0.1234 '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_publ_flag
C15 Pd1 C1 89.97(4) yes
C15 Pd1 Cl2 171.67(3) ?
C1 Pd1 Cl2 86.64(2) ?
C15 Pd1 Cl1 91.49(3) ?
C1 Pd1 Cl1 177.52(2) ?
Cl2 Pd1 Cl1 91.648(9) yes
C7 C8 H8A 109.5 ?
C7 C8 H8B 109.5 ?
C7 C8 H8C 109.5 ?
C3 C8B H8B1 109.5 ?
C3 C8B H8B2 109.5 ?
H8B1 C8B H8B2 109.5 ?
C3 C8B H8B3 109.5 ?
H8B1 C8B H8B3 109.5 ?
H8B2 C8B H8B3 109.5 ?
O1 S1 O2 120.48(5) ?
O1 S1 N3 102.75(4) ?
O2 S1 N3 106.63(4) ?
O1 S1 C9 109.93(5) ?
O2 S1 C9 108.79(5) ?
N3 S1 C9 107.39(4) ?
C1 N1 C2 125.18(7) ?
C1 N1 H1N 116.4(11) ?
C2 N1 H1N 118.4(11) ?
C1 N2 N3 120.21(7) ?
C1 N2 H2N 119.8(11) ?
N3 N2 H2N 117.0(11) ?
N2 N3 S1 115.64(6) ?
N2 N3 H3N 108.9(12) ?
S1 N3 H3N 112.5(12) ?
C15 N4 C16 174.94(10) ?
N1 C1 N2 117.84(7) yes
N1 C1 Pd1 125.65(6) ?
N2 C1 Pd1 116.41(6) ?
C3 C2 C7 120.31(8) ?
C3 C2 N1 120.82(8) ?
C7 C2 N1 118.61(8) ?
C4 C3 C2 120.19(9) ?
C4 C3 C8B 118.5(3) ?
C2 C3 C8B 121.3(3) ?
C4 C3 Cl3 119.17(8) ?
C2 C3 Cl3 120.54(7) ?
C5 C4 C3 119.29(10) ?
C5 C4 H4 120.4 ?
C3 C4 H4 120.4 ?
C6 C5 C4 120.63(9) ?
C6 C5 H5 119.7 ?
C4 C5 H5 119.7 ?
C5 C6 C7 120.83(10) ?
C5 C6 H6 119.6 ?
C7 C6 H6 119.6 ?
C6 C7 C2 118.70(9) ?
C6 C7 C8 120.3(3) ?
C2 C7 C8 121.0(3) ?
C6 C7 Cl3B 121.76(14) ?
C2 C7 Cl3B 119.51(13) ?
C10 C9 C14 121.85(9) ?
C10 C9 S1 119.62(8) ?
C14 C9 S1 118.53(8) ?
C9 C10 C11 118.55(10) ?
C9 C10 H10 120.7 ?
C11 C10 H10 120.7 ?
C12 C11 C10 120.22(11) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C13 C12 C11 120.45(11) ?
C13 C12 H12 119.8 ?
C11 C12 H12 119.8 ?
C14 C13 C12 120.27(11) ?
C14 C13 H13 119.9 ?
C12 C13 H13 119.9 ?
C13 C14 C9 118.65(10) ?
C13 C14 H14 120.7 ?
C9 C14 H14 120.7 ?
N4 C15 Pd1 173.86(9) ?
N4 C16 C17 119.80(9) ?
N4 C16 C21 118.52(9) ?
C17 C16 C21 121.68(9) ?
C18 C17 C16 119.95(10) ?
C18 C17 Cl4 120.22(8) ?
C16 C17 Cl4 119.83(7) ?
C19 C18 C17 118.88(10) ?
C19 C18 H18 120.6 ?
C17 C18 H18 120.6 ?
C18 C19 C20 121.04(10) ?
C18 C19 H19 119.5 ?
C20 C19 H19 119.5 ?
C19 C20 C21 121.18(11) ?
C19 C20 H20 119.4 ?
C21 C20 H20 119.4 ?
C20 C21 C16 117.27(10) ?
C20 C21 C22 121.67(10) ?
C16 C21 C22 121.04(9) ?
C21 C22 H22A 109.5 ?
C21 C22 H22B 109.5 ?
H22A C22 H22B 109.5 ?
C21 C22 H22C 109.5 ?
H22A C22 H22C 109.5 ?
H22B C22 H22C 109.5 ?
Cl5 C23 Cl6 112.21(6) ?
Cl5 C23 H23A 109.2 ?
Cl6 C23 H23A 109.2 ?
Cl5 C23 H23B 109.2 ?
Cl6 C23 H23B 109.2 ?
H23A C23 H23B 107.9 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C15 1.9261(9) yes
Pd1 C1 1.9761(8) yes
Pd1 Cl2 2.3149(2) yes
Pd1 Cl1 2.3663(2) yes
Cl3 C3 1.7417(10) ?
C8 C7 1.482(4) ?
C8 H8A 0.9800 ?
C8 H8B 0.9800 ?
C8 H8C 0.9800 ?
C8B C3 1.462(6) ?
C8B H8B1 0.9800 ?
C8B H8B2 0.9800 ?
C8B H8B3 0.9800 ?
Cl3B C7 1.774(2) ?
Cl4 C17 1.7233(11) ?
Cl5 C23 1.7619(12) ?
Cl6 C23 1.7682(13) ?
S1 O1 1.4321(8) ?
S1 O2 1.4341(8) ?
S1 N3 1.6665(8) ?
S1 C9 1.7554(10) ?
N1 C1 1.3174(11) yes
N1 C2 1.4269(11) yes
N1 H1N 0.855(17) ?
N2 C1 1.3356(11) yes
N2 N3 1.4065(10) yes
N2 H2N 0.850(16) ?
N3 H3N 0.821(17) ?
N4 C15 1.1562(12) ?
N4 C16 1.3917(12) ?
C2 C3 1.3944(13) ?
C2 C7 1.3994(13) ?
C3 C4 1.3927(13) ?
C4 C5 1.3851(17) ?
C4 H4 0.9500 ?
C5 C6 1.3829(17) ?
C5 H5 0.9500 ?
C6 C7 1.3904(14) ?
C6 H6 0.9500 ?
C9 C10 1.3914(14) ?
C9 C14 1.3940(14) ?
C10 C11 1.3922(17) ?
C10 H10 0.9500 ?
C11 C12 1.3897(19) ?
C11 H11 0.9500 ?
C12 C13 1.3885(18) ?
C12 H12 0.9500 ?
C13 C14 1.3882(15) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
C16 C17 1.3952(14) ?
C16 C21 1.4012(14) ?
C17 C18 1.3887(14) ?
C18 C19 1.3861(18) ?
C18 H18 0.9500 ?
C19 C20 1.3883(17) ?
C19 H19 0.9500 ?
C20 C21 1.3933(15) ?
C20 H20 0.9500 ?
C21 C22 1.5244(16) ?
C22 H22A 0.9800 ?
C22 H22B 0.9800 ?
C22 H22C 0.9800 ?
C23 H23A 0.9900 ?
C23 H23B 0.9900 ?
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
N3 H3N Cl1 0.821(17) 2.341(17) 3.1533(8) 170.1(16) 2_565 yes
N2 H2N Cl2 0.850(16) 2.365(16) 3.1897(8) 163.7(14) 2_565 yes
