#------------------------------------------------------------------------------
#$Date: 2019-10-28 11:16:04 +0200 (Mon, 28 Oct 2019) $
#$Revision: 220005 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/48/4514844.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_4514844
loop_
_publ_author_name
'Romine, Andrew M.'
'Yang, Kin S.'
'Karunananda, Malkanthi K.'
'Chen, Jason S.'
'Engle, Keary M.'
_publ_section_title
;
 Synthetic and Mechanistic Studies of a Versatile Heteroaryl Thioether
 Directing Group for Pd(II) Catalysis
;
_journal_issue                   9
_journal_name_full               'ACS Catalysis'
_journal_page_first              7626
_journal_paper_doi               10.1021/acscatal.9b01471
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C38 H30 F6 N2 O4 Pd S4'
_chemical_formula_sum            'C38 H30 F6 N2 O4 Pd S4'
_chemical_formula_weight         927.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-05-11
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.408(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.3360(10)
_cell_length_b                   10.1947(7)
_cell_length_c                   24.0955(13)
_cell_measurement_reflns_used    5162
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.271
_cell_measurement_theta_min      2.685
_cell_volume                     3726.7(4)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2016)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 8.258
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            12876
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.293
_diffrn_reflns_theta_min         1.709
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.797
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0803 before and 0.0412 after correction. The Ratio of minimum to maximum transmission is 0.8765. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_description       block
_exptl_crystal_F_000             1872
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.242
_refine_diff_density_min         -1.118
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.361
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         4617
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.361
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0674
_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)+(0.0213P)²+34.8463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1418
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3955
_reflns_number_total             4617
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs9b01471_si_013.cif
_cod_data_source_block           engle122_0m_a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4514844
_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_max   0.870
_shelx_estimated_absorpt_t_min   0.826
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C5(H5), C12(H12), C13(H13), C19(H19), C15(H15),
 C18(H18), C17(H17), C16(H16)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.5000 0.01730(14) Uani 1 2 d S T P
S1 S 0.23225(8) 0.32994(13) 0.43344(5) 0.0226(3) Uani 1 1 d . . .
S2 S 0.41968(8) 0.24847(14) 0.42096(5) 0.0247(3) Uani 1 1 d . . .
F1 F 0.5004(2) 0.4500(4) 0.68996(12) 0.0377(8) Uani 1 1 d . . .
O1 O 0.4972(2) 0.4637(3) 0.58150(13) 0.0200(7) Uani 1 1 d . . .
O2 O 0.4652(2) 0.2470(4) 0.57339(14) 0.0254(8) Uani 1 1 d . . .
N1 N 0.3724(2) 0.4453(4) 0.48230(15) 0.0166(8) Uani 1 1 d . . .
F3 F 0.3712(2) 0.3795(5) 0.66043(15) 0.0541(12) Uani 1 1 d . . .
F2 F 0.4769(4) 0.2432(4) 0.68569(15) 0.0631(13) Uani 1 1 d . . .
C2 C 0.4763(3) 0.3509(5) 0.59775(18) 0.0181(9) Uani 1 1 d . . .
C9 C 0.3460(3) 0.3501(5) 0.44768(18) 0.0195(10) Uani 1 1 d . . .
C3 C 0.3016(3) 0.5087(5) 0.50250(18) 0.0206(9) Uani 1 1 d . . .
C4 C 0.3080(3) 0.6079(5) 0.5422(2) 0.0230(10) Uani 1 1 d . . .
H4 H 0.3639 0.6394 0.5593 0.028 Uiso 1 1 calc R . .
C8 C 0.2189(3) 0.4605(5) 0.47849(19) 0.0200(10) Uani 1 1 d . . .
C1 C 0.4576(4) 0.3566(5) 0.6598(2) 0.0270(11) Uani 1 1 d . . .
C6 C 0.1476(4) 0.6135(5) 0.5309(2) 0.0286(12) Uani 1 1 d . . .
H6 H 0.0955 0.6519 0.5407 0.034 Uiso 1 1 calc R . .
C7 C 0.1408(3) 0.5140(6) 0.4920(2) 0.0278(11) Uani 1 1 d . . .
H7 H 0.0849 0.4826 0.4750 0.033 Uiso 1 1 calc R . .
C5 C 0.2305(4) 0.6598(5) 0.5564(2) 0.0261(11) Uani 1 1 d . . .
H5 H 0.2333 0.7275 0.5837 0.031 Uiso 1 1 calc R . .
C12 C 0.4817(4) 0.1218(6) 0.3228(2) 0.0330(13) Uani 1 1 d . . .
H12 H 0.4706 0.1974 0.2998 0.040 Uiso 1 1 calc R . .
C10 C 0.3470(3) 0.1536(6) 0.3691(2) 0.0289(12) Uani 1 1 d . . .
H10A H 0.3024 0.1064 0.3873 0.035 Uiso 1 1 calc R . .
H10B H 0.3160 0.2124 0.3400 0.035 Uiso 1 1 calc R . .
C13 C 0.5644(4) 0.0807(6) 0.3354(2) 0.0343(13) Uani 1 1 d . . .
H13 H 0.5744 0.0035 0.3575 0.041 Uiso 1 1 calc R . .
C14 C 0.6410(4) 0.1444(6) 0.3180(2) 0.0352(13) Uani 1 1 d . . .
C19 C 0.6415(4) 0.2759(6) 0.3039(3) 0.0387(14) Uani 1 1 d . . .
H19 H 0.5911 0.3286 0.3063 0.046 Uiso 1 1 calc R . .
C11 C 0.4051(4) 0.0558(6) 0.3428(3) 0.0384(14) Uani 1 1 d . . .
H11A H 0.4270 -0.0119 0.3708 0.046 Uiso 1 1 calc R . .
H11B H 0.3691 0.0113 0.3107 0.046 Uiso 1 1 calc R . .
C15 C 0.7173(4) 0.0725(8) 0.3153(3) 0.0500(17) Uani 1 1 d . . .
H15 H 0.7195 -0.0173 0.3260 0.060 Uiso 1 1 calc R . .
C18 C 0.7147(5) 0.3309(8) 0.2863(3) 0.0519(18) Uani 1 1 d . . .
H18 H 0.7139 0.4211 0.2764 0.062 Uiso 1 1 calc R . .
C17 C 0.7894(5) 0.2574(9) 0.2827(4) 0.065(2) Uani 1 1 d . . .
H17 H 0.8394 0.2957 0.2700 0.078 Uiso 1 1 calc R . .
C16 C 0.7896(5) 0.1297(9) 0.2975(4) 0.071(3) Uani 1 1 d . . .
H16 H 0.8407 0.0782 0.2957 0.085 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'
F F 0.0171 0.0103 '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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
O1 Pd1 O1 180.0 5_666 .
O1 Pd1 N1 90.16(14) 5_666 .
O1 Pd1 N1 89.84(14) 5_666 5_666
O1 Pd1 N1 89.84(14) . .
O1 Pd1 N1 90.16(14) . 5_666
N1 Pd1 N1 180.0 5_666 .
C9 S1 C8 89.6(2) . .
C9 S2 C10 101.9(2) . .
C2 O1 Pd1 120.8(3) . .
C9 N1 Pd1 122.7(3) . .
C9 N1 C3 112.3(4) . .
C3 N1 Pd1 124.9(3) . .
O1 C2 C1 110.5(4) . .
O2 C2 O1 131.7(4) . .
O2 C2 C1 117.6(4) . .
S2 C9 S1 123.2(3) . .
N1 C9 S1 115.0(4) . .
N1 C9 S2 121.7(3) . .
C4 C3 N1 126.3(4) . .
C4 C3 C8 120.6(5) . .
C8 C3 N1 113.1(4) . .
C3 C4 C5 118.1(5) . .
C3 C8 S1 110.0(4) . .
C7 C8 S1 128.6(4) . .
C7 C8 C3 121.4(5) . .
F1 C1 F3 106.4(5) . .
F1 C1 F2 108.2(4) . .
F1 C1 C2 114.1(4) . .
F3 C1 C2 109.5(4) . .
F2 C1 F3 107.3(5) . .
F2 C1 C2 111.0(4) . .
C7 C6 C5 121.2(5) . .
C6 C7 C8 117.7(5) . .
C4 C5 C6 121.0(5) . .
C13 C12 C11 123.6(6) . .
C11 C10 S2 107.1(4) . .
C12 C13 C14 125.2(6) . .
C19 C14 C13 122.5(6) . .
C19 C14 C15 117.6(6) . .
C15 C14 C13 119.8(6) . .
C18 C19 C14 120.3(7) . .
C12 C11 C10 111.8(5) . .
C16 C15 C14 120.9(8) . .
C19 C18 C17 121.3(7) . .
C16 C17 C18 118.4(7) . .
C17 C16 C15 121.3(8) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 O1 2.005(3) 5_666
Pd1 O1 2.005(3) .
Pd1 N1 2.020(4) 5_666
Pd1 N1 2.020(4) .
S1 C9 1.740(5) .
S1 C8 1.748(5) .
S2 C9 1.726(5) .
S2 C10 1.825(5) .
F1 C1 1.313(6) .
O1 C2 1.271(6) .
O2 C2 1.211(6) .
N1 C9 1.305(6) .
N1 C3 1.410(6) .
F3 C1 1.348(7) .
F2 C1 1.326(7) .
C2 C1 1.565(6) .
C3 C4 1.386(7) .
C3 C8 1.403(6) .
C4 C5 1.389(7) .
C8 C7 1.398(7) .
C6 C7 1.374(8) .
C6 C5 1.410(8) .
C12 C13 1.328(8) .
C12 C11 1.494(8) .
C10 C11 1.535(8) .
C13 C14 1.456(9) .
C14 C19 1.384(9) .
C14 C15 1.390(9) .
C19 C18 1.376(9) .
C15 C16 1.376(11) .
C18 C17 1.382(11) .
C17 C16 1.350(13) .
