#------------------------------------------------------------------------------
#$Date: 2024-12-06 20:14:20 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296499 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/72/7717251.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_7717251
loop_
_publ_author_name
'Palio, Lorenzo'
'Bru, Francis'
'Ruggiero, Tommaso'
'Bourda, Laurens'
'Van Hecke, Kristof'
'Cazin, Catherine'
'Nolan, Steven P.'
_publ_section_title
;
 The role of the stabilizing/leaving group in palladium catalysed
 cross-coupling reactions.
;
_journal_issue                   44
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              18013
_journal_page_last               18020
_journal_paper_doi               10.1039/d4dt02533d
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C26 H22 Cl2 Pd2'
_chemical_formula_sum            'C26 H22 Cl2 Pd2'
_chemical_formula_weight         618.13
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-27
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-03 deposited with the CCDC.	2024-10-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.767(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.7576(2)
_cell_length_b                   5.86520(10)
_cell_length_c                   17.7802(3)
_cell_measurement_reflns_used    6851
_cell_measurement_temperature    293.15(1)
_cell_measurement_theta_max      73.1740
_cell_measurement_theta_min      4.0480
_cell_volume                     1185.64(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293.15(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4839
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 -30.00   81
  2  ω   -116.00 -17.00   1.00    1.00    --  -41.68 -38.00 150.00   99
  3  ω    -21.00  74.00   1.00    1.00    --   41.68 -77.00 -60.00   95
  4  ω     97.00 178.00   1.00   12.50    --  106.01 125.00   0.00   81
  5  ω     33.00 132.00   1.00   12.50    --  106.01 -45.00-120.00   99
  6  ω    103.00 178.00   1.00   12.50    --  106.01  77.00 -90.00   75
  7  ω     34.00 135.00   1.00   12.50    --  106.01 -61.00 150.00  101
  8  ω     18.00 178.00   1.00   12.50    --  106.01   0.00-120.00  160
  9  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00   0.00  101
 10  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00 -90.00  101
 11  ω     33.00 112.00   1.00   12.50    --  106.01-125.00 120.00   79
 12  ω     77.00 178.00   1.00   12.50    --  106.01  61.00 -60.00  101
 13  ω     77.00 178.00   1.00   12.50    --  106.01  61.00  90.00  101
 14  ω     53.00 178.00   1.00   12.50    --  106.01  15.00  60.00  125
 15  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00  90.00  101
 16  ω    -87.00  -6.00   1.00    1.00    --  -41.68 125.00 120.00   81
 17  ω     33.00 112.00   1.00   12.50    --  106.01-125.00  60.00   79
 18  ω     77.00 178.00   1.00   12.50    --  106.01  61.00-180.00  101
 19  ω     80.00 178.00   1.00   12.50    --  106.01  45.00 150.00   98
 20  ω     77.00 178.00   1.00   12.50    --  106.01  61.00-120.00  101
 21  ω   -115.00 -14.00   1.00    1.00    --  -41.68 -57.00-180.00  101
 22  ω    -66.00  33.00   1.00    1.00    --  -41.68  38.00-120.00   99
 23  ω     33.00 112.00   1.00   12.50    --  106.01-125.00-180.00   79
 24  ω     77.00 166.00   1.00   12.50    --  106.01  61.00 -90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0898509000
_diffrn_orient_matrix_UB_12      -0.1909594000
_diffrn_orient_matrix_UB_13      0.0003170000
_diffrn_orient_matrix_UB_21      0.0496353000
_diffrn_orient_matrix_UB_22      -0.1373466000
_diffrn_orient_matrix_UB_23      -0.0583062000
_diffrn_orient_matrix_UB_31      0.0884546000
_diffrn_orient_matrix_UB_32      -0.1168568000
_diffrn_orient_matrix_UB_33      0.0680461000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16213
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.674
_diffrn_reflns_theta_min         4.078
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    14.377
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.513
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_description       needle
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         2384
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0312
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0401P)²+0.1968P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0830
_refine_ls_wR_factor_ref         0.0913
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2006
_reflns_number_total             2384
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02533d2.cif
_cod_data_source_block           fb183_dcmhex2
_cod_depositor_comments
'Adding full bibliography for 7717248--7717252.cif.'
_cod_database_code               7717251
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H Cl Pd'
_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   0.393
_shelx_estimated_absorpt_t_min   0.091
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2), C3(H3)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13)
;
_olex2_date_sample_data_collection 2022-07-26
_olex2_exptl_crystal_mounting_method 'Mounted on a LythoLoop'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 6.350
_oxdiff_exptl_absorpt_empirical_full_min 0.675
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
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.60592(3) 0.81153(6) 0.54754(2) 0.07972(14) Uani 1 1 d . . . . .
Cl1 Cl 0.59380(10) 1.1051(2) 0.45169(7) 0.0956(3) Uani 1 1 d . . . . .
C1 C 0.7713(5) 0.6637(12) 0.5522(4) 0.1088(16) Uani 1 1 d . . . . .
H1A H 0.771305 0.527899 0.521049 0.131 Uiso 1 1 calc R U . . .
H1B H 0.835297 0.767850 0.551944 0.131 Uiso 1 1 calc R U . . .
C2 C 0.7422(5) 0.6344(12) 0.6232(4) 0.1078(16) Uani 1 1 d . . . . .
H2 H 0.789208 0.711108 0.669814 0.129 Uiso 1 1 calc R U . . .
C3 C 0.6404(5) 0.5261(10) 0.6262(3) 0.0993(14) Uani 1 1 d . . . . .
H3 H 0.630872 0.379865 0.598688 0.119 Uiso 1 1 calc R U . . .
C4 C 0.5876(4) 0.5241(7) 0.6927(3) 0.0811(9) Uani 1 1 d . . . . .
C5 C 0.6128(6) 0.6858(10) 0.7507(4) 0.1086(16) Uani 1 1 d . . . . .
H5 H 0.665449 0.801177 0.747359 0.130 Uiso 1 1 calc R U . . .
C6 C 0.5652(7) 0.6860(11) 0.8124(4) 0.117(2) Uani 1 1 d . . . . .
H6 H 0.584926 0.800002 0.849796 0.141 Uiso 1 1 calc R U . . .
C7 C 0.4870(4) 0.5163(10) 0.8196(3) 0.0991(13) Uani 1 1 d . . . . .
C8 C 0.4350(6) 0.5115(13) 0.8849(4) 0.1196(18) Uani 1 1 d . . . . .
H8 H 0.452426 0.624844 0.922731 0.143 Uiso 1 1 calc R U . . .
C9 C 0.3610(6) 0.3403(15) 0.8904(5) 0.130(2) Uani 1 1 d . . . . .
H9 H 0.329911 0.333533 0.933512 0.156 Uiso 1 1 calc R U . . .
C10 C 0.3305(6) 0.1775(16) 0.8346(7) 0.144(3) Uani 1 1 d . . . . .
H10 H 0.277362 0.064269 0.839177 0.173 Uiso 1 1 calc R U . . .
C11 C 0.3763(6) 0.1784(12) 0.7730(5) 0.129(2) Uani 1 1 d . . . . .
H11 H 0.354440 0.065055 0.735524 0.155 Uiso 1 1 calc R U . . .
C12 C 0.4555(4) 0.3441(9) 0.7637(3) 0.0910(12) Uani 1 1 d . . . . .
C13 C 0.5088(5) 0.3533(9) 0.6994(3) 0.0992(14) Uani 1 1 d . . . . .
H13 H 0.490046 0.241559 0.661086 0.119 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'
Cl Cl 0.3639 0.7018 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 -10 0.0470
2 0 10 0.0470
-4 3 2 0.1019
4 -3 -2 0.1019
6 0 -9 0.0380
-6 0 9 0.0380
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
_geom_angle_publ_flag
Cl1 Pd1 Cl1 88.68(4) . 3_676 ?
C1 Pd1 Cl1 102.10(18) . . ?
C1 Pd1 Cl1 167.2(2) . 3_676 ?
C1 Pd1 C3 68.7(2) . . ?
C2 Pd1 Cl1 133.50(16) . 3_676 ?
C2 Pd1 Cl1 135.35(17) . . ?
C2 Pd1 C1 39.0(2) . . ?
C2 Pd1 C3 37.6(2) . . ?
C3 Pd1 Cl1 100.20(15) . 3_676 ?
C3 Pd1 Cl1 170.43(14) . . ?
Pd1 Cl1 Pd1 91.32(4) . 3_676 ?
Pd1 C1 H1A 116.7 . . ?
Pd1 C1 H1B 116.7 . . ?
H1A C1 H1B 113.7 . . ?
C2 C1 Pd1 69.6(3) . . ?
C2 C1 H1A 116.7 . . ?
C2 C1 H1B 116.7 . . ?
Pd1 C2 H2 119.4 . . ?
C1 C2 Pd1 71.4(3) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 Pd1 73.8(3) . . ?
C3 C2 C1 120.6(6) . . ?
C3 C2 H2 119.4 . . ?
Pd1 C3 H3 112.1 . . ?
C2 C3 Pd1 68.6(3) . . ?
C2 C3 H3 112.1 . . ?
C2 C3 C4 126.1(6) . . ?
C4 C3 Pd1 118.7(3) . . ?
C4 C3 H3 112.1 . . ?
C5 C4 C3 122.9(5) . . ?
C5 C4 C13 116.9(5) . . ?
C13 C4 C3 120.1(5) . . ?
C4 C5 H5 118.2 . . ?
C6 C5 C4 123.7(6) . . ?
C6 C5 H5 118.2 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.8(6) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 C12 121.0(6) . . ?
C12 C7 C8 117.9(5) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 119.1(7) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.2 . . ?
C8 C9 C10 121.7(7) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(7) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.6(8) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C13 116.6(5) . . ?
C11 C12 C7 119.1(6) . . ?
C11 C12 C13 124.3(6) . . ?
C4 C13 C12 122.0(5) . . ?
C4 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 Cl1 2.4021(11) 3_676 ?
Pd1 Cl1 2.4013(13) . ?
Pd1 C1 2.111(5) . ?
Pd1 C2 2.088(6) . ?
Pd1 C3 2.153(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.401(8) . ?
C2 H2 0.9800 . ?
C2 C3 1.367(9) . ?
C3 H3 0.9800 . ?
C3 C4 1.469(7) . ?
C4 C5 1.377(7) . ?
C4 C13 1.389(7) . ?
C5 H5 0.9300 . ?
C5 C6 1.351(9) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(8) . ?
C7 C8 1.444(8) . ?
C7 C12 1.399(8) . ?
C8 H8 0.9300 . ?
C8 C9 1.349(10) . ?
C9 H9 0.9300 . ?
C9 C10 1.358(12) . ?
C10 H10 0.9300 . ?
C10 C11 1.337(14) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(8) . ?
C12 C13 1.440(8) . ?
C13 H13 0.9300 . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Pd1 C1 C2 C3 57.2(5) . . . . ?
Pd1 C2 C3 C4 -110.7(5) . . . . ?
Pd1 C3 C4 C5 -62.4(7) . . . . ?
Pd1 C3 C4 C13 117.9(5) . . . . ?
C1 C2 C3 Pd1 -56.1(5) . . . . ?
C1 C2 C3 C4 -166.8(5) . . . . ?
C2 C3 C4 C5 21.0(9) . . . . ?
C2 C3 C4 C13 -158.6(5) . . . . ?
C3 C4 C5 C6 -179.8(6) . . . . ?
C3 C4 C13 C12 179.7(5) . . . . ?
C4 C5 C6 C7 0.4(12) . . . . ?
C5 C4 C13 C12 0.0(8) . . . . ?
C5 C6 C7 C8 179.7(7) . . . . ?
C5 C6 C7 C12 -0.4(11) . . . . ?
C6 C7 C8 C9 -178.7(7) . . . . ?
C6 C7 C12 C11 -179.6(7) . . . . ?
C6 C7 C12 C13 0.2(8) . . . . ?
C7 C8 C9 C10 -2.6(12) . . . . ?
C7 C12 C13 C4 0.0(8) . . . . ?
C8 C7 C12 C11 0.3(9) . . . . ?
C8 C7 C12 C13 -179.9(5) . . . . ?
C8 C9 C10 C11 2.0(13) . . . . ?
C9 C10 C11 C12 -0.2(13) . . . . ?
C10 C11 C12 C7 -0.9(11) . . . . ?
C10 C11 C12 C13 179.3(7) . . . . ?
C11 C12 C13 C4 179.8(6) . . . . ?
C12 C7 C8 C9 1.4(10) . . . . ?
C13 C4 C5 C6 -0.2(10) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.8064 0.2428 -10.1223 0.1127 0.4672 -0.8769
1.8064 -0.2428 10.1223 -0.1127 -0.4672 0.8769
-4.4526 3.0826 2.4486 -0.1878 -0.7872 -0.5875
4.4526 -3.0826 -2.4486 0.1878 0.7872 0.5875
6.1158 0.4873 -8.8793 -0.6454 0.7544 -0.1202
-6.1158 -0.4873 8.8793 0.6454 -0.7544 0.1202
