#------------------------------------------------------------------------------
#$Date: 2019-11-23 08:55:04 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232606 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/34/79/4347976.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_4347976
loop_
_publ_author_name
'Schlindwein, Simon H.'
'Bader, Katharina'
'Sibold, Carlo'
'Frey, Wolfgang'
'Neugebauer, Petr'
'Orlita, Milan'
'Slageren, Joris van'
'Gudat, Dietrich'
_publ_section_title
;
 New Selective Synthesis of Dithiaboroles as a Viable Pathway to
 Functionalized Benzenedithiolenes and Their Complexes.
;
_journal_issue                   12
_journal_name_full               'Inorganic chemistry'
_journal_page_first              6186
_journal_page_last               6194
_journal_paper_doi               10.1021/acs.inorgchem.6b00821
_journal_volume                  55
_journal_year                    2016
_chemical_formula_sum            'C44 H46 N2 O2 P2 Pd S4'
_chemical_formula_weight         931.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.460(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   14.2038(10)
_cell_length_b                   8.1279(5)
_cell_length_c                   19.2114(13)
_cell_measurement_reflns_used    2751
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.277
_cell_measurement_theta_min      3.445
_cell_volume                     2127.0(3)
_computing_cell_refinement       'Bruker ApexII Software Suite, 2008'
_computing_data_collection       'Bruker ApexII Software Suite, 2008'
_computing_data_reduction        'Bruker ApexII Software Suite, 2008'
_computing_molecular_graphics    'SHELXS plus XP (Sheldrick, 1991)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_device_type  'Bruker Kappa ApexII Duo'
_diffrn_measurement_method       'Omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0638
_diffrn_reflns_av_unetI/netI     0.0597
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14085
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_theta_full        66.277
_diffrn_reflns_theta_max         66.277
_diffrn_reflns_theta_min         3.445
_exptl_absorpt_coefficient_mu    6.373
_exptl_absorpt_correction_T_max  0.8787
_exptl_absorpt_correction_T_min  0.3440
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'BLESSING 1995'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_description       plate
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.026
_refine_diff_density_max         1.777
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.113
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0467
_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)+(0.0767P)²+1.4589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1305
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2751
_reflns_number_total             3584
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            12(gud243).cif
_cod_data_source_block           gud243
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4347976
_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   0.310
_shelx_estimated_absorpt_t_max   0.852
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -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 0.0000 0.5000 0.0000 0.01607(17) Uani 1 2 d S . P
S1 S -0.00375(9) 0.72885(14) 0.07180(6) 0.0204(3) Uani 1 1 d . . .
S2 S -0.14897(10) 0.80474(18) 0.17279(7) 0.0306(3) Uani 1 1 d . . .
H2S H -0.086(5) 0.711(8) 0.171(4) 0.06(2) Uiso 1 1 d . . .
P1 P 0.07364(9) 0.35694(15) 0.10408(6) 0.0171(3) Uani 1 1 d . . .
C1 C -0.1441(4) 0.8949(6) -0.0352(3) 0.0207(11) Uani 1 1 d . . .
C2 C -0.1154(3) 0.8358(5) 0.0365(3) 0.0183(10) Uani 1 1 d . . .
C3 C -0.1755(4) 0.8716(6) 0.0812(3) 0.0240(11) Uani 1 1 d . . .
C4 C 0.1982(3) 0.4187(6) 0.1493(2) 0.0179(10) Uani 1 1 d . . .
C5 C 0.0080(4) 0.3610(6) 0.1719(3) 0.0213(11) Uani 1 1 d . . .
C6 C -0.2613(4) 0.9650(6) 0.0548(3) 0.0265(12) Uani 1 1 d . . .
H6 H -0.3010 0.9894 0.0858 0.032 Uiso 1 1 calc R U .
C7 C -0.2888(4) 1.0220(6) -0.0162(3) 0.0261(12) Uani 1 1 d . . .
H7 H -0.3468 1.0856 -0.0339 0.031 Uiso 1 1 calc R U .
C8 C -0.2305(4) 0.9850(6) -0.0607(3) 0.0236(11) Uani 1 1 d . . .
H8 H -0.2497 1.0217 -0.1096 0.028 Uiso 1 1 calc R U .
C9 C 0.2562(4) 0.3305(6) 0.2093(3) 0.0204(11) Uani 1 1 d . . .
H9 H 0.2287 0.2399 0.2280 0.024 Uiso 1 1 calc R U .
C10 C 0.3525(4) 0.3748(6) 0.2411(3) 0.0248(12) Uani 1 1 d . . .
H10 H 0.3904 0.3167 0.2825 0.030 Uiso 1 1 calc R U .
C11 C 0.3942(4) 0.5038(6) 0.2131(3) 0.0235(11) Uani 1 1 d . . .
H11 H 0.4613 0.5314 0.2342 0.028 Uiso 1 1 calc R U .
C12 C 0.3383(4) 0.5924(6) 0.1544(3) 0.0229(11) Uani 1 1 d . . .
H12 H 0.3665 0.6822 0.1357 0.027 Uiso 1 1 calc R U .
C13 C 0.2404(4) 0.5494(6) 0.1227(3) 0.0197(11) Uani 1 1 d . . .
H13 H 0.2022 0.6105 0.0824 0.024 Uiso 1 1 calc R U .
C14 C 0.0421(4) 0.4469(6) 0.2375(3) 0.0253(12) Uani 1 1 d . . .
H14 H 0.1028 0.5042 0.2478 0.030 Uiso 1 1 calc R U .
C15 C -0.0116(4) 0.4492(7) 0.2873(3) 0.0319(13) Uani 1 1 d . . .
H15 H 0.0116 0.5088 0.3314 0.038 Uiso 1 1 calc R U .
C16 C -0.0999(4) 0.3635(8) 0.2724(3) 0.0369(14) Uani 1 1 d . . .
H16 H -0.1361 0.3625 0.3071 0.044 Uiso 1 1 calc R U .
C17 C -0.1353(4) 0.2803(7) 0.2080(3) 0.0338(14) Uani 1 1 d . . .
H17 H -0.1963 0.2241 0.1979 0.041 Uiso 1 1 calc R U .
C18 C -0.0826(4) 0.2785(6) 0.1583(3) 0.0263(12) Uani 1 1 d . . .
H18 H -0.1075 0.2206 0.1139 0.032 Uiso 1 1 calc R U .
C19 C 0.0822(4) 0.1372(6) 0.0855(3) 0.0213(11) Uani 1 1 d . . .
H19A H 0.1108 0.0785 0.1318 0.026 Uiso 1 1 calc R U .
H19B H 0.0154 0.0931 0.0636 0.026 Uiso 1 1 calc R U .
O1D O -0.5080(3) 0.7358(5) 0.0520(3) 0.0475(12) Uani 1 1 d . . .
N1D N -0.3778(4) 0.5613(7) 0.0660(3) 0.0380(12) Uani 1 1 d . . .
C1D C -0.4397(5) 0.6795(8) 0.0322(4) 0.0472(18) Uani 1 1 d . . .
H1D H -0.4298 0.7237 -0.0109 0.057 Uiso 1 1 calc R U .
C2D C -0.3895(5) 0.4781(8) 0.1300(4) 0.0477(17) Uani 1 1 d . . .
H2D1 H -0.3373 0.3962 0.1466 0.072 Uiso 1 1 calc R U .
H2D2 H -0.3856 0.5589 0.1686 0.072 Uiso 1 1 calc R U .
H2D3 H -0.4535 0.4232 0.1180 0.072 Uiso 1 1 calc R U .
C3D C -0.3001(5) 0.5027(9) 0.0374(4) 0.0483(17) Uani 1 1 d . . .
H3D1 H -0.2628 0.4168 0.0694 0.072 Uiso 1 1 calc R U .
H3D2 H -0.3286 0.4574 -0.0113 0.072 Uiso 1 1 calc R U .
H3D3 H -0.2563 0.5943 0.0349 0.072 Uiso 1 1 calc R U .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
P1 Pd1 P1 180.0 . 3_565
P1 Pd1 S1 91.73(4) . 3_565
P1 Pd1 S1 88.27(4) 3_565 3_565
P1 Pd1 S1 88.27(4) . .
P1 Pd1 S1 91.73(4) 3_565 .
S1 Pd1 S1 180.0 3_565 .
C2 S1 Pd1 109.57(15) . .
C3 S2 H2S 97(3) . .
C5 P1 C4 106.5(2) . .
C5 P1 C19 103.6(2) . .
C4 P1 C19 104.7(2) . .
C5 P1 Pd1 114.78(16) . .
C4 P1 Pd1 114.89(16) . .
C19 P1 Pd1 111.31(16) . .
C8 C1 C2 120.3(5) . .
C8 C1 C19 118.9(4) . 3_565
C2 C1 C19 120.7(4) . 3_565
C3 C2 C1 118.1(4) . .
C3 C2 S1 120.2(4) . .
C1 C2 S1 121.6(4) . .
C6 C3 C2 120.5(5) . .
C6 C3 S2 116.3(4) . .
C2 C3 S2 123.2(4) . .
C13 C4 C9 118.5(4) . .
C13 C4 P1 120.2(3) . .
C9 C4 P1 121.2(4) . .
C14 C5 C18 118.0(5) . .
C14 C5 P1 122.7(4) . .
C18 C5 P1 119.3(4) . .
C7 C6 C3 120.7(5) . .
C7 C6 H6 119.7 . .
C3 C6 H6 119.7 . .
C8 C7 C6 118.9(5) . .
C8 C7 H7 120.5 . .
C6 C7 H7 120.5 . .
C7 C8 C1 121.4(5) . .
C7 C8 H8 119.3 . .
C1 C8 H8 119.3 . .
C10 C9 C4 120.5(5) . .
C10 C9 H9 119.8 . .
C4 C9 H9 119.8 . .
C9 C10 C11 120.3(4) . .
C9 C10 H10 119.8 . .
C11 C10 H10 119.8 . .
C12 C11 C10 120.0(5) . .
C12 C11 H11 120.0 . .
C10 C11 H11 120.0 . .
C11 C12 C13 119.8(5) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C4 C13 C12 120.9(4) . .
C4 C13 H13 119.6 . .
C12 C13 H13 119.6 . .
C15 C14 C5 120.7(5) . .
C15 C14 H14 119.6 . .
C5 C14 H14 119.6 . .
C14 C15 C16 119.5(5) . .
C14 C15 H15 120.3 . .
C16 C15 H15 120.3 . .
C17 C16 C15 120.7(6) . .
C17 C16 H16 119.7 . .
C15 C16 H16 119.7 . .
C18 C17 C16 120.0(5) . .
C18 C17 H17 120.0 . .
C16 C17 H17 120.0 . .
C17 C18 C5 121.1(5) . .
C17 C18 H18 119.4 . .
C5 C18 H18 119.4 . .
C1 C19 P1 112.2(3) 3_565 .
C1 C19 H19A 109.2 3_565 .
P1 C19 H19A 109.2 . .
C1 C19 H19B 109.2 3_565 .
P1 C19 H19B 109.2 . .
H19A C19 H19B 107.9 . .
C1D N1D C3D 121.3(6) . .
C1D N1D C2D 121.7(6) . .
C3D N1D C2D 116.8(5) . .
O1D C1D N1D 125.9(7) . .
O1D C1D H1D 117.1 . .
N1D C1D H1D 117.1 . .
N1D C2D H2D1 109.5 . .
N1D C2D H2D2 109.5 . .
H2D1 C2D H2D2 109.5 . .
N1D C2D H2D3 109.5 . .
H2D1 C2D H2D3 109.5 . .
H2D2 C2D H2D3 109.5 . .
N1D C3D H3D1 109.5 . .
N1D C3D H3D2 109.5 . .
H3D1 C3D H3D2 109.5 . .
N1D C3D H3D3 109.5 . .
H3D1 C3D H3D3 109.5 . .
H3D2 C3D H3D3 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 P1 2.2932(11) .
Pd1 P1 2.2933(11) 3_565
Pd1 S1 2.3253(12) 3_565
Pd1 S1 2.3253(12) .
S1 C2 1.767(5) .
S2 C3 1.776(5) .
S2 H2S 1.19(7) .
P1 C5 1.805(5) .
P1 C4 1.807(5) .
P1 C19 1.832(5) .
C1 C8 1.393(7) .
C1 C2 1.406(7) .
C1 C19 1.502(7) 3_565
C2 C3 1.403(7) .
C3 C6 1.403(7) .
C4 C13 1.387(7) .
C4 C9 1.408(7) .
C5 C14 1.401(7) .
C5 C18 1.408(7) .
C6 C7 1.388(8) .
C6 H6 0.9500 .
C7 C8 1.381(8) .
C7 H7 0.9500 .
C8 H8 0.9500 .
C9 C10 1.379(7) .
C9 H9 0.9500 .
C10 C11 1.387(7) .
C10 H10 0.9500 .
C11 C12 1.384(7) .
C11 H11 0.9500 .
C12 C13 1.395(7) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.383(8) .
C14 H14 0.9500 .
C15 C16 1.391(9) .
C15 H15 0.9500 .
C16 C17 1.374(8) .
C16 H16 0.9500 .
C17 C18 1.370(8) .
C17 H17 0.9500 .
C18 H18 0.9500 .
C19 C1 1.502(7) 3_565
C19 H19A 0.9900 .
C19 H19B 0.9900 .
O1D C1D 1.227(8) .
N1D C1D 1.340(8) .
N1D C3D 1.444(8) .
N1D C2D 1.454(8) .
C1D H1D 0.9500 .
C2D H2D1 0.9800 .
C2D H2D2 0.9800 .
C2D H2D3 0.9800 .
C3D H3D1 0.9800 .
C3D H3D2 0.9800 .
C3D H3D3 0.9800 .
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_1
_geom_torsion_site_symmetry_4
C8 C1 C2 C3 -0.6(7) . .
C19 C1 C2 C3 179.1(4) 3_565 .
C8 C1 C2 S1 -177.2(4) . .
C19 C1 C2 S1 2.5(6) 3_565 .
Pd1 S1 C2 C3 126.2(4) . .
Pd1 S1 C2 C1 -57.2(4) . .
C1 C2 C3 C6 -0.5(7) . .
S1 C2 C3 C6 176.2(4) . .
C1 C2 C3 S2 179.8(4) . .
S1 C2 C3 S2 -3.5(6) . .
C5 P1 C4 C13 -125.0(4) . .
C19 P1 C4 C13 125.7(4) . .
Pd1 P1 C4 C13 3.3(5) . .
C5 P1 C4 C9 58.6(5) . .
C19 P1 C4 C9 -50.7(5) . .
Pd1 P1 C4 C9 -173.1(3) . .
C4 P1 C5 C14 18.4(5) . .
C19 P1 C5 C14 128.5(4) . .
Pd1 P1 C5 C14 -110.0(4) . .
C4 P1 C5 C18 -163.4(4) . .
C19 P1 C5 C18 -53.2(4) . .
Pd1 P1 C5 C18 68.3(4) . .
C2 C3 C6 C7 0.7(8) . .
S2 C3 C6 C7 -179.5(4) . .
C3 C6 C7 C8 0.2(8) . .
C6 C7 C8 C1 -1.3(8) . .
C2 C1 C8 C7 1.5(7) . .
C19 C1 C8 C7 -178.2(4) 3_565 .
C13 C4 C9 C10 0.6(7) . .
P1 C4 C9 C10 177.1(4) . .
C4 C9 C10 C11 -1.9(8) . .
C9 C10 C11 C12 2.2(8) . .
C10 C11 C12 C13 -1.2(8) . .
C9 C4 C13 C12 0.3(7) . .
P1 C4 C13 C12 -176.2(4) . .
C11 C12 C13 C4 0.0(8) . .
C18 C5 C14 C15 0.4(7) . .
P1 C5 C14 C15 178.7(4) . .
C5 C14 C15 C16 0.8(8) . .
C14 C15 C16 C17 -1.7(9) . .
C15 C16 C17 C18 1.3(9) . .
C16 C17 C18 C5 -0.1(8) . .
C14 C5 C18 C17 -0.8(7) . .
P1 C5 C18 C17 -179.2(4) . .
C5 P1 C19 C1 -174.1(3) . 3_565
C4 P1 C19 C1 -62.7(4) . 3_565
Pd1 P1 C19 C1 62.1(3) . 3_565
C3D N1D C1D O1D 179.4(6) . .
C2D N1D C1D O1D 3.7(10) . .
