#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:50:05 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178703 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/14/4081474.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_4081474
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         'C20 H30 Cl2 N4 O2 Pd S'
_chemical_formula_sum            'C20 H30 Cl2 N4 O2 Pd S'
_chemical_formula_weight         567.84
_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                105.097(2)
_cell_angle_beta                 105.810(2)
_cell_angle_gamma                90.071(2)
_cell_formula_units_Z            2
_cell_length_a                   9.8749(3)
_cell_length_b                   10.5459(3)
_cell_length_c                   12.6529(4)
_cell_measurement_reflns_used    9201
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.10
_cell_measurement_theta_min      2.89
_cell_volume                     1220.36(7)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0222
_diffrn_reflns_av_sigmaI/netI    0.0312
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            30639
_diffrn_reflns_theta_full        33.40
_diffrn_reflns_theta_max         33.40
_diffrn_reflns_theta_min         1.74
_exptl_absorpt_coefficient_mu    1.088
_exptl_absorpt_correction_T_max  0.8990
_exptl_absorpt_correction_T_min  0.6870
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             580
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.10
_refine_diff_density_max         1.357
_refine_diff_density_min         -0.990
_refine_diff_density_rms         0.099
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         9271
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0286
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0208P)²+1.3002P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0658
_reflns_number_gt                7694
_reflns_number_total             9271
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4007592_si_003.cif
_cod_data_source_block           34
_cod_original_cell_volume        1220.36(6)
_cod_database_code               4081474
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
Pd1 Pd 0.889273(13) 0.539109(12) 0.163715(11) 0.01368(3) Uani 1 1 d .
Cl1 Cl 0.85713(5) 0.76715(4) 0.19063(4) 0.01945(8) Uani 1 1 d .
Cl2 Cl 1.13130(4) 0.56952(4) 0.19781(4) 0.01898(8) Uani 1 1 d .
S1 S 0.80628(5) 0.06617(4) -0.10621(4) 0.01798(8) Uani 1 1 d .
O1 O 0.87024(15) -0.04736(12) -0.15613(12) 0.0257(3) Uani 1 1 d .
O2 O 0.73647(15) 0.06385(13) -0.02155(12) 0.0262(3) Uani 1 1 d .
N1 N 0.95667(16) 0.26878(14) 0.17877(12) 0.0169(3) Uani 1 1 d .
H1 H 0.976(2) 0.193(2) 0.1467(18) 0.018(5) Uiso 1 1 d .
N2 N 0.90100(16) 0.30545(13) 0.00284(12) 0.0159(3) Uani 1 1 d .
H2 H 0.888(3) 0.356(2) -0.040(2) 0.032(7) Uiso 1 1 d .
N3 N 0.94007(16) 0.17997(14) -0.04441(12) 0.0168(3) Uani 1 1 d .
H3 H 0.996(2) 0.182(2) -0.0841(18) 0.016(5) Uiso 1 1 d .
N4 N 0.58280(17) 0.47458(17) 0.15568(15) 0.0263(3) Uani 1 1 d .
C1 C 0.91741(16) 0.34929(15) 0.11582(14) 0.0145(3) Uani 1 1 d .
C2 C 0.96746(18) 0.29277(16) 0.30013(14) 0.0165(3) Uani 1 1 d .
H2A H 0.9104 0.3680 0.3228 0.020 Uiso 1 1 calc R
C3 C 1.1205(2) 0.32736(19) 0.37282(16) 0.0239(4) Uani 1 1 d .
H3A H 1.1804 0.2596 0.3436 0.029 Uiso 1 1 calc R
H3B H 1.1544 0.4131 0.3673 0.029 Uiso 1 1 calc R
C4 C 1.1337(3) 0.3351(2) 0.49740(17) 0.0341(5) Uani 1 1 d .
H4A H 1.2343 0.3529 0.5422 0.041 Uiso 1 1 calc R
H4B H 1.0816 0.4090 0.5288 0.041 Uiso 1 1 calc R
C5 C 1.0754(3) 0.2080(2) 0.50923(18) 0.0400(6) Uani 1 1 d .
H5A H 1.0841 0.2163 0.5906 0.048 Uiso 1 1 calc R
H5B H 1.1309 0.1348 0.4821 0.048 Uiso 1 1 calc R
C6 C 0.9211(3) 0.1773(2) 0.4402(2) 0.0377(5) Uani 1 1 d .
H6A H 0.8644 0.2471 0.4713 0.045 Uiso 1 1 calc R
H6B H 0.8857 0.0926 0.4468 0.045 Uiso 1 1 calc R
C7 C 0.9040(2) 0.16868(19) 0.31512(16) 0.0242(4) Uani 1 1 d .
H7A H 0.8023 0.1553 0.2731 0.029 Uiso 1 1 calc R
H7B H 0.9506 0.0915 0.2818 0.029 Uiso 1 1 calc R
C9 C 0.68704(18) 0.11371(16) -0.21811(15) 0.0177(3) Uani 1 1 d .
C10 C 0.5540(2) 0.14826(18) -0.20866(17) 0.0245(4) Uani 1 1 d .
H10 H 0.5292 0.1523 -0.1405 0.029 Uiso 1 1 calc R
C11 C 0.4583(2) 0.1767(2) -0.30102(19) 0.0294(4) Uani 1 1 d .
H11 H 0.3667 0.1998 -0.2964 0.035 Uiso 1 1 calc R
C12 C 0.4958(2) 0.17141(19) -0.39942(18) 0.0281(4) Uani 1 1 d .
H12 H 0.4294 0.1902 -0.4624 0.034 Uiso 1 1 calc R
C13 C 0.6298(2) 0.13888(19) -0.40729(16) 0.0247(4) Uani 1 1 d .
H13 H 0.6551 0.1368 -0.4749 0.030 Uiso 1 1 calc R
C14 C 0.72619(19) 0.10958(17) -0.31640(15) 0.0205(3) Uani 1 1 d .
H14 H 0.8179 0.0869 -0.3211 0.025 Uiso 1 1 calc R
C15 C 0.69404(19) 0.49894(17) 0.15201(16) 0.0200(3) Uani 1 1 d .
C16 C 0.4480(2) 0.4363(2) 0.1700(2) 0.0325(5) Uani 1 1 d .
H16 H 0.3752 0.4946 0.1414 0.039 Uiso 1 1 calc R
C17 C 0.4034(2) 0.2938(3) 0.0998(2) 0.0421(6) Uani 1 1 d .
H17A H 0.3058 0.2710 0.0990 0.051 Uiso 1 1 calc R
H17B H 0.4040 0.2849 0.0200 0.051 Uiso 1 1 calc R
C18 C 0.5011(2) 0.1981(2) 0.1477(2) 0.0370(5) Uani 1 1 d .
H18A H 0.4654 0.1067 0.1030 0.044 Uiso 1 1 calc R
H18B H 0.5965 0.2141 0.1403 0.044 Uiso 1 1 calc R
C19 C 0.5105(2) 0.2142(2) 0.2725(2) 0.0320(4) Uani 1 1 d .
H19A H 0.5769 0.1531 0.3022 0.038 Uiso 1 1 calc R
H19B H 0.4165 0.1913 0.2793 0.038 Uiso 1 1 calc R
C20 C 0.5607(2) 0.35497(19) 0.34311(18) 0.0268(4) Uani 1 1 d .
H20A H 0.6586 0.3746 0.3427 0.032 Uiso 1 1 calc R
H20B H 0.5611 0.3642 0.4231 0.032 Uiso 1 1 calc R
C21 C 0.4659(2) 0.4535(2) 0.29645(19) 0.0294(4) Uani 1 1 d .
H21A H 0.3720 0.4428 0.3083 0.035 Uiso 1 1 calc R
H21B H 0.5069 0.5440 0.3397 0.035 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'
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'
Pd Pd -0.9988 1.0072 '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'
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 90.81(7) yes
C15 Pd1 Cl2 171.44(5) ?
C1 Pd1 Cl2 84.94(5) ?
C15 Pd1 Cl1 91.94(5) ?
C1 Pd1 Cl1 170.53(5) ?
Cl2 Pd1 Cl1 93.447(15) yes
O2 S1 O1 121.06(8) ?
O2 S1 N3 106.46(8) ?
O1 S1 N3 103.67(8) ?
O2 S1 C9 108.25(8) ?
O1 S1 C9 107.74(8) ?
N3 S1 C9 109.20(8) ?
C1 N1 C2 127.24(14) ?
C1 N1 H1 117.4(15) ?
C2 N1 H1 115.3(15) ?
C1 N2 N3 120.62(14) ?
C1 N2 H2 122.6(17) ?
N3 N2 H2 115.0(17) ?
N2 N3 S1 114.24(11) ?
N2 N3 H3 112.9(14) ?
S1 N3 H3 114.3(14) ?
C15 N4 C16 173.71(19) ?
N1 C1 N2 118.79(14) yes
N1 C1 Pd1 128.78(12) ?
N2 C1 Pd1 112.28(11) ?
N1 C2 C3 110.97(14) ?
N1 C2 C7 107.21(14) ?
C3 C2 C7 112.00(14) ?
N1 C2 H2A 108.9 ?
C3 C2 H2A 108.9 ?
C7 C2 H2A 108.9 ?
C4 C3 C2 110.72(17) ?
C4 C3 H3A 109.5 ?
C2 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
C2 C3 H3B 109.5 ?
H3A C3 H3B 108.1 ?
C5 C4 C3 111.31(17) ?
C5 C4 H4A 109.4 ?
C3 C4 H4A 109.4 ?
C5 C4 H4B 109.4 ?
C3 C4 H4B 109.4 ?
H4A C4 H4B 108.0 ?
C4 C5 C6 110.57(18) ?
C4 C5 H5A 109.5 ?
C6 C5 H5A 109.5 ?
C4 C5 H5B 109.5 ?
C6 C5 H5B 109.5 ?
H5A C5 H5B 108.1 ?
C5 C6 C7 110.66(18) ?
C5 C6 H6A 109.5 ?
C7 C6 H6A 109.5 ?
C5 C6 H6B 109.5 ?
C7 C6 H6B 109.5 ?
H6A C6 H6B 108.1 ?
C6 C7 C2 112.01(17) ?
C6 C7 H7A 109.2 ?
C2 C7 H7A 109.2 ?
C6 C7 H7B 109.2 ?
C2 C7 H7B 109.2 ?
H7A C7 H7B 107.9 ?
C14 C9 C10 121.51(17) ?
C14 C9 S1 118.80(13) ?
C10 C9 S1 119.62(14) ?
C11 C10 C9 118.63(18) ?
C11 C10 H10 120.7 ?
C9 C10 H10 120.7 ?
C12 C11 C10 120.21(18) ?
C12 C11 H11 119.9 ?
C10 C11 H11 119.9 ?
C11 C12 C13 120.69(18) ?
C11 C12 H12 119.7 ?
C13 C12 H12 119.7 ?
C14 C13 C12 119.87(18) ?
C14 C13 H13 120.1 ?
C12 C13 H13 120.1 ?
C13 C14 C9 119.07(17) ?
C13 C14 H14 120.5 ?
C9 C14 H14 120.5 ?
N4 C15 Pd1 173.43(17) ?
N4 C16 C21 108.68(17) ?
N4 C16 C17 108.47(18) ?
C21 C16 C17 111.95(18) ?
N4 C16 H16 109.2 ?
C21 C16 H16 109.2 ?
C17 C16 H16 109.2 ?
C18 C17 C16 111.80(18) ?
C18 C17 H17A 109.3 ?
C16 C17 H17A 109.3 ?
C18 C17 H17B 109.3 ?
C16 C17 H17B 109.3 ?
H17A C17 H17B 107.9 ?
C19 C18 C17 111.09(19) ?
C19 C18 H18A 109.4 ?
C17 C18 H18A 109.4 ?
C19 C18 H18B 109.4 ?
C17 C18 H18B 109.4 ?
H18A C18 H18B 108.0 ?
C18 C19 C20 110.83(17) ?
C18 C19 H19A 109.5 ?
C20 C19 H19A 109.5 ?
C18 C19 H19B 109.5 ?
C20 C19 H19B 109.5 ?
H19A C19 H19B 108.1 ?
C19 C20 C21 111.39(18) ?
C19 C20 H20A 109.3 ?
C21 C20 H20A 109.3 ?
C19 C20 H20B 109.3 ?
C21 C20 H20B 109.3 ?
H20A C20 H20B 108.0 ?
C16 C21 C20 112.53(17) ?
C16 C21 H21A 109.1 ?
C20 C21 H21A 109.1 ?
C16 C21 H21B 109.1 ?
C20 C21 H21B 109.1 ?
H21A C21 H21B 107.8 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Pd1 C15 1.9308(18) yes
Pd1 C1 1.9781(16) yes
Pd1 Cl2 2.3163(4) yes
Pd1 Cl1 2.3737(4) yes
S1 O2 1.4281(14) ?
S1 O1 1.4341(13) ?
S1 N3 1.6557(15) ?
S1 C9 1.7622(18) ?
N1 C1 1.300(2) yes
N1 C2 1.463(2) yes
N1 H1 0.84(2) ?
N2 C1 1.346(2) ?
N2 N3 1.4044(19) yes
N2 H2 0.84(3) ?
N3 H3 0.84(2) ?
N4 C15 1.144(2) ?
N4 C16 1.461(2) ?
C2 C3 1.527(2) ?
C2 C7 1.528(2) ?
C2 H2A 1.0000 ?
C3 C4 1.526(3) ?
C3 H3A 0.9900 ?
C3 H3B 0.9900 ?
C4 C5 1.517(4) ?
C4 H4A 0.9900 ?
C4 H4B 0.9900 ?
C5 C6 1.521(4) ?
C5 H5A 0.9900 ?
C5 H5B 0.9900 ?
C6 C7 1.524(3) ?
C6 H6A 0.9900 ?
C6 H6B 0.9900 ?
C7 H7A 0.9900 ?
C7 H7B 0.9900 ?
C9 C14 1.390(2) ?
C9 C10 1.391(2) ?
C10 C11 1.389(3) ?
C10 H10 0.9500 ?
C11 C12 1.381(3) ?
C11 H11 0.9500 ?
C12 C13 1.390(3) ?
C12 H12 0.9500 ?
C13 C14 1.383(3) ?
C13 H13 0.9500 ?
C14 H14 0.9500 ?
C16 C21 1.523(3) ?
C16 C17 1.527(4) ?
C16 H16 1.0000 ?
C17 C18 1.523(4) ?
C17 H17A 0.9900 ?
C17 H17B 0.9900 ?
C18 C19 1.520(3) ?
C18 H18A 0.9900 ?
C18 H18B 0.9900 ?
C19 C20 1.521(3) ?
C19 H19A 0.9900 ?
C19 H19B 0.9900 ?
C20 C21 1.525(3) ?
C20 H20A 0.9900 ?
C20 H20B 0.9900 ?
C21 H21A 0.9900 ?
C21 H21B 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
N2 H2 Cl2 0.84(3) 2.30(3) 3.0967(15) 161(2) 2_765 yes
N3 H3 Cl1 0.84(2) 2.38(2) 3.2091(15) 168.2(19) 2_765 yes
N1 H1 O1 0.84(2) 2.16(2) 2.8957(19) 145(2) 2_755 yes
