Hydroxyl-functionalized triazolylidene-based PEPPSI complexes: metallacycle formation effect on the Suzuki coupling reaction.
Rendón-Nava, David; Álvarez-Hernández, Alejandro; Rheingold, Arnold L.; Suárez-Castillo, Oscar R; Mendoza-Espinosa, Daniel; Dalton transactions (Cambridge, England : 2003) 48 (2019) 3214–3222; doi:10.1039/c8dt04432e

data_7048608
_publ_section_title
;
 Hydroxyl-functionalized triazolylidene-based PEPPSI complexes:
 metallacycle formation effect on the Suzuki coupling reaction.
;
_journal_issue                   10
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              3214
_journal_page_last               3222
_journal_paper_doi               10.1039/c8dt04432e
_journal_volume                  48
_journal_year                    2019
_chemical_formula_moiety         'C18 H22 I2 N4 O Pd'
_chemical_formula_sum            'C18 H22 I2 N4 O Pd'
_chemical_formula_weight         670.59
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2018-12-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2018-12-21 deposited with the CCDC.
2019-01-10 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 109.756(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.8996(6)
_cell_length_b                   12.0868(5)
_cell_length_c                   16.6138(8)
_cell_measurement_reflns_used    19050
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4560
_cell_measurement_theta_min      3.3220
_cell_volume                     2248.9(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3659
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -67.00  -37.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  126.0000  124.7369 30

  2 omega  -18.00   87.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454   77.0000 -180.0000 105

  3 omega  -17.00   52.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -99.0000 -180.0000 69

  4 omega  -21.00   52.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -99.0000   30.0000 73

  5 omega  -44.00   40.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -57.0000  -90.0000 84

  6 omega  -26.00   87.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454   19.0000    0.0000 113

  7 omega  -12.00   86.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454   37.0000   90.0000 98

  8 omega    7.00   53.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454 -100.0000   93.3470 46

  9 omega  -83.00   18.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  -57.0000 -180.0000 101

 10 omega  -45.00   18.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610   86.0000  115.0000 63

 11 omega  -38.00   63.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610   57.0000  -90.0000 101

 12 omega  -25.00   52.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -99.0000   60.0000 77

 13 omega  -21.00   88.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454   77.0000  -30.0000 109

 14 omega  -65.00   44.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -77.0000 -120.0000 109

 15 omega  -25.00   31.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  -99.0000   30.0000 56

 16 omega  -67.00  -19.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  126.0000   85.1513 48

 17 omega  -74.00  -27.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  138.0000  150.0254 47

 18 omega  -69.00  -22.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  129.0000 -114.1398 47

 19 omega  -25.00   52.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -99.0000  -30.0000 77

 20 omega  -24.00   53.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454 -100.0000   93.3470 77

 21 omega  -68.00  -21.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  128.0000  -56.5181 47

 22 omega  -85.00  -36.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  153.0000  166.3471 49

 23 omega  -84.00   14.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       -9.9610  -37.0000  -60.0000 98

 24 omega  -77.00   53.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454    0.0000 -180.0000 130

 25 omega  -25.00   52.00   1.0000    2.4250
omega____ theta____ kappa____ phi______ frames
    -       11.4454  -99.0000  120.0000 77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0443384000
_diffrn_orient_matrix_UB_12      0.0383676000
_diffrn_orient_matrix_UB_13      -0.0229488000
_diffrn_orient_matrix_UB_21      -0.0226299000
_diffrn_orient_matrix_UB_22      -0.0392017000
_diffrn_orient_matrix_UB_23      -0.0333498000
_diffrn_orient_matrix_UB_31      -0.0391219000
_diffrn_orient_matrix_UB_32      -0.0208713000
_diffrn_orient_matrix_UB_33      0.0204893000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            56197
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.074
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.981
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.959
_refine_diff_density_min         -0.581
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3954
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.119
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0326
_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^)+(0.0274P)^2^+7.2996P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0729
_refine_ls_wR_factor_ref         0.0839
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3293
_reflns_number_total             3954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8dt04432e2.cif
_cod_data_source_block           dm-44
_cod_depositor_comments
'Adding full bibliography for 7048608--7048609.cif.'
_cod_original_cell_volume        2248.89(19)
_cod_database_code               7048608
_shelxl_version_number           2014/6
_chemical_oxdiff_formula         'C17 H14 N4 O Pd I2'
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Me refined with riding coordinates:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C3(H3A,H3B,H3C), C13(H13A,H13B,H13C)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C7(H7), C14(H14), C18(H18), C16(H16), C15(H15), C17(H17)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              30550
_olex2_submission_special_instructions 'No special instructions were received'