Mononuclear palladium(ii) and platinum(ii) complexes of P,C-donor ligands: synthesis, crystal structures, cytotoxicity, and mechanistic studies of a highly stereoselective Mizoroki‒Heck reaction
Sabounchei, Seyyed Javad; Hosseinzadeh, Marjan; Salehzadeh, Sadegh; Maleki, Farahnaz; Gable, Robert W.; Inorganic Chemistry Frontiers 4 (2017) 2107–; doi:10.1039/C7QI00568G

data_4349785
_publ_section_title
;
 Mononuclear palladium(ii) and platinum(ii) complexes of P,C-donor
 ligands: synthesis, crystal structures, cytotoxicity, and mechanistic
 studies of a highly stereoselective Mizoroki--Heck reaction
;
_journal_issue                   12
_journal_name_full               'Inorganic Chemistry Frontiers'
_journal_page_first              2107
_journal_paper_doi               10.1039/C7QI00568G
_journal_volume                  4
_journal_year                    2017
_chemical_formula_moiety         'C40 H34 Cl2 O P2 Pd'
_chemical_formula_sum            'C40 H34 Cl2 O P2 Pd'
_chemical_formula_weight         769.91
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-10
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.16 svn.r3265 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2017-09-10 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.6167(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.4290(2)
_cell_length_b                   16.4777(3)
_cell_length_c                   27.0274(5)
_cell_measurement_reflns_used    31276
_cell_measurement_temperature    129.99(10)
_cell_measurement_theta_max      77.0700
_cell_measurement_theta_min      3.1180
_cell_volume                     6870.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      129.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.2273
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -47.00  26.00   1.00    2.23    --  -41.87  37.00   0.00   73
  2  \w    -32.00  21.00   1.00    2.23    --  -41.87  37.00 -60.00   53
  3  \w    -31.00  61.00   1.00    2.23    --   41.87 -77.00 120.00   92
  4  \w      2.00  31.00   1.00    2.23    --   41.87 -99.00  90.00   29
  5  \w     55.00 105.00   1.00    8.89    --  112.00 -94.00  60.00   50
  6  \w     91.00 116.00   1.00    8.89    --  112.00-111.00  90.00   25
  7  \w    109.00 139.00   1.00    8.89    --  112.00 -77.00 150.00   30
  8  \w    116.00 155.00   1.00    8.89    --  112.00 -15.00  60.00   39
  9  \w    144.00 171.00   1.00    8.89    --  112.00  45.00 120.00   27
 10  \w    133.00 158.00   1.00    8.89    --  112.00  77.00  60.00   25
 11  \w    134.00 160.00   1.00    8.89    --  112.00  61.00 -30.00   26
 12  \w    153.00 178.00   1.00    8.89    --  112.00  30.00-150.00   25
 13  \w    104.00 130.00   1.00    8.89    --  112.00 -77.00   0.00   26
 14  \w     83.00 114.00   1.00    8.89    --  112.00-111.00  30.00   31
 15  \w     77.00 116.00   1.00    8.89    --  112.00-111.00 -60.00   39
 16  \w     62.00  94.00   1.00    8.89    --  112.00-111.00-150.00   32
 17  \w     83.00 116.00   1.00    8.89    --  112.00-111.00-180.00   33
 18  \w     68.00 114.00   1.00    8.89    --  112.00-111.00-120.00   46
 19  \w     58.00  91.00   1.00    8.89    --  112.00 -30.00 -60.00   33
 20  \w     85.00 155.00   1.00    8.89    --  112.00 -15.00-120.00   70
 21  \w     98.00 170.00   1.00    8.89    --  112.00  45.00-120.00   72
 22  \w     85.00 128.00   1.00    8.89    --  112.00  30.00-150.00   43
 23  \w     90.00 115.00   1.00    8.89    --  112.00  61.00 -30.00   25
 24  \w     92.00 123.00   1.00    8.89    --  112.00  77.00  60.00   31
 25  \w     86.00 121.00   1.00    8.89    --  112.00  45.00 120.00   35
 26  \w     45.00 135.00   1.00    8.89    --  112.00 -61.00   0.00   90
 27  \w     73.00 112.00   1.00    8.89    --  112.00-111.00 150.00   39
 28  \w     40.00  97.00   1.00    8.89    --  112.00 -45.00 150.00   57
 29  \w     40.00  76.00   1.00    8.89    --  112.00 -94.00 150.00   36
 30  \w     38.00  67.00   1.00    8.89    --  112.00 -77.00 150.00   29
 31  \w     31.00 103.00   1.00    8.89    --  112.00 -15.00  60.00   72
 32  \w     56.00  92.00   1.00    8.89    --  112.00 -77.00   0.00   36
 33  \w     47.00  96.00   1.00    8.89    --  112.00-111.00 -30.00   49
 34  \w     52.00  98.00   1.00    8.89    --  112.00-111.00 -90.00   46
 35  \w     57.00  97.00   1.00    8.89    --  112.00 -45.00-150.00   40
 36  \w     40.00  66.00   1.00    8.89    --  112.00-111.00 -60.00   26
 37  \w     43.00 112.00   1.00    8.89    --  112.00-111.00   0.00   69
 38  \w     42.00  73.00   1.00    8.89    --  112.00 -94.00   0.00   31
 39  \w     36.00  68.00   1.00    8.89    --  112.00 -30.00   0.00   32
 40  \w     32.00  67.00   1.00    8.89    --  112.00 -15.00-120.00   35
 41  \w     40.00  71.00   1.00    8.89    --  112.00 -30.00-150.00   31
 42  \w    -82.00  -2.00   1.00    2.23    --  -41.87 125.00 -30.00   80
 43  \w    -88.00 -55.00   1.00    2.23    --  -41.87 125.00-180.00   33
 44  \w   -108.00 -24.00   1.00    2.23    --  -41.87 -37.00-180.00   84
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0494729000
_diffrn_orient_matrix_UB_12      0.0417116000
_diffrn_orient_matrix_UB_13      -0.0421958000
_diffrn_orient_matrix_UB_21      -0.0051267000
_diffrn_orient_matrix_UB_22      -0.0786513000
_diffrn_orient_matrix_UB_23      -0.0306953000
_diffrn_orient_matrix_UB_31      -0.0865814000
_diffrn_orient_matrix_UB_32      0.0284897000
_diffrn_orient_matrix_UB_33      -0.0229826000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            25031
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        75.000
_diffrn_reflns_theta_max         77.325
_diffrn_reflns_theta_min         3.141
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    6.912
_exptl_absorpt_correction_T_max  0.626
_exptl_absorpt_correction_T_min  0.160
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_description       needle
_exptl_crystal_F_000             3136
_exptl_crystal_recrystallization_method
'from vapour diffusion of methanol into DMSO'
_exptl_crystal_size_max          0.387
_exptl_crystal_size_mid          0.193
_exptl_crystal_size_min          0.11
_refine_diff_density_max         2.709
_refine_diff_density_min         -1.681
_refine_diff_density_rms         0.135
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     830
_refine_ls_number_reflns         25031
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0726
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0370P)^2^+54.8779P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1808
_refine_ls_wR_factor_ref         0.1840
_reflns_Friedel_coverage         0.000
_reflns_number_gt                22258
_reflns_number_total             25031
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qi00568g2.cif
_cod_data_source_block           rwg2016_6agau
_cod_original_cell_volume        6870.90(19)
_cod_database_code               4349785
_chemical_oxdiff_formula         'C40 H34 Cl2 O P2 Pd'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.5340(14) 0.4660(14)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3.a Ternary CH refined with riding coordinates:
 C14(H14), C54(H54)
3.b Secondary CH2 refined with riding coordinates:
 C27(H27A,H27B), C28(H28A,H28B), C67(H67A,H67B), C68(H68A,H68B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26), C30(H30), C31(H31), C32(H32), C33(H33), C34(H34),
 C36(H36), C37(H37), C38(H38), C39(H39), C40(H40), C42(H42), C43(H43), C44(H44),
  C45(H45), C46(H46), C48(H48), C49(H49), C51(H51), C52(H52), C60(H60),
 C59(H59), C58(H58), C57(H57), C56(H56), C62(H62), C63(H63), C64(H64), C65(H65),
  C66(H66), C70(H70), C71(H71), C72(H72), C73(H73), C74(H74), C76(H76),
 C77(H77), C78(H78), C79(H79), C80(H80)
;
_shelx_res_checksum              86684
_shelx_hkl_checksum              87071
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method mounted
_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 1.728
_oxdiff_exptl_absorpt_empirical_full_min 0.460
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
_rwg_local_checkcif_report
;
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) Range 3.1 Ratio

    Some of the C atoms in the phenyl rings have larger Ueq due to free
    movement

PLAT234_ALERT_4_C Large Hirshfeld Difference C63 -- C64 .. 0.16 Ang.

    Atome were correctly assigned

PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds ............. 0.01614 Ang.

    Disorder, twinning & presence of heavy atoms

PLAT906_ALERT_3_C Large K value in the Analysis of Variance .... 4.457 Check

    Disorder & twinning

PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) . 1 Check

    Disorder and twinning; reflection was retained in data set

PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large 54.88 Why ?

   See PLAT906_ALERT_3_C above

PLAT793_ALERT_4_G The Model has Chirality at C14 (Centro SPGR) R Verify
PLAT793_ALERT_4_G The Model has Chirality at C54 (Centro SPGR) R Verify

    Correct

PLAT870_ALERT_4_G ALERTS Related to Twinning Effects Suppressed .. ! Info

    The data was processed as a TWIN & refined using HKLF 5 data

PLAT910_ALERT_3_G Missing No. of FCF Reflection(s) Below Th(Min) ... 1 Report

    Reflection behind beam stop

PLAT912_ALERT_4_G Missing No. of FCF Reflections Above STh/L= 0.600 90 Note

    Reflections were in detector rejection region and 9 reflections were
    omitted where Iobs >> Icalc, due to incomplete processing during
    TWIN processing

PLAT931_ALERT_5_G Found Twin Law ( )[ 0 0 1] Estimated BASF 0.32 Check

    The data was processed as a TWIN & refined using HKLF 5 data
;
_twin_special_details
;
Component 2 rotated by 179.9820\% 
 around [-0.00 0.00 1.00] (reciprocal) or [0.02 -0.00 1.00] (direct)
;