Synthesis of unsymmetrical NCN′ and PCN pincer palladacycles and their catalytic evaluation compared with a related SCN pincer palladacycle
Roffe, Gavin W.; Tizzard, Graham J.; Coles, Simon J.; Cox, Hazel; Spencer, John; Organic Chemistry Frontiers 3 (2016) 957–; doi:10.1039/C6QO00198J

data_1553472
_publ_section_title
;
 Synthesis of unsymmetrical NCN&#x2032; and PCN pincer palladacycles and
 their catalytic evaluation compared with a related SCN pincer
 palladacycle
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              957
_journal_paper_doi               10.1039/C6QO00198J
_journal_volume                  3
_journal_year                    2016
_chemical_formula_moiety         'C23 H17 Cl N O P Pd'
_chemical_formula_sum            'C23 H17 Cl N O P Pd'
_chemical_formula_weight         496.20
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-25
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-04-26 deposited with the CCDC.
2016-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                91.535(3)
_cell_angle_beta                 108.207(3)
_cell_angle_gamma                112.231(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0641(2)
_cell_length_b                   9.6782(3)
_cell_length_c                   12.7031(4)
_cell_measurement_reflns_used    9668
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.5560
_cell_measurement_theta_min      2.3700
_cell_volume                     966.47(6)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection
'CrystalClear-SM Expert 3.1 b27 (Rigaku, 2013)'
_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_temperature      100(2)
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HG Saturn724+ (2x2 bin mode)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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   -107.00  73.00   1.00    5.00    --  -17.00   8.00 -17.00  180
  2  \w    -77.00  22.00   1.00    5.00    --  -17.00 -72.00  81.00   99
  3  \w    -84.00  22.00   1.00    5.00    --  -17.00 -72.00-115.00  106
  4  \w    -27.00  71.00   1.00    5.00    --  -17.00  72.00 -17.00   98
  5  \w    -72.00 -57.00   1.00    5.00    --  -17.00 -40.00-180.00   15
  6  \w    -67.00  -7.00   1.00    5.00    --  -17.00   8.00  16.00   60
;
_diffrn_measurement_device       'four-circle \k goniometer'
_diffrn_measurement_device_type
'Rigaku FRE+ equipped with HF Varimax confocal mirrors and an AFC12 goniometer and HG Saturn 724+ detector'
_diffrn_measurement_method       'profile data from \w-scans'
_diffrn_measurement_specimen_support 'MiTeGen MicroLoop'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018243000
_diffrn_orient_matrix_UB_12      0.0091225000
_diffrn_orient_matrix_UB_13      0.0551051000
_diffrn_orient_matrix_UB_21      -0.0031598000
_diffrn_orient_matrix_UB_22      0.0714621000
_diffrn_orient_matrix_UB_23      -0.0067335000
_diffrn_orient_matrix_UB_31      -0.0901220000
_diffrn_orient_matrix_UB_32      -0.0354068000
_diffrn_orient_matrix_UB_33      -0.0216718000
_diffrn_radiation_collimation    0.2
_diffrn_radiation_monochromator  'Confocal mirrors, HF Varimax'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0144
_diffrn_reflns_av_unetI/netI     0.0132
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11298
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.559
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           55.0
_diffrn_source_power             2.475
_diffrn_source_target            Mo
_diffrn_source_type              'Rigaku FRE+'
_diffrn_source_voltage           45.0
_exptl_absorpt_coefficient_mu    1.195
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.489
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0201
_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^)+(0.0266P)^2^+0.9105P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0508
_refine_ls_wR_factor_ref         0.0514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4218
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6qo00198j2.cif
_cod_data_source_block           7b
_cod_original_cell_volume        966.48(5)
_cod_database_code               1553472
_chemical_oxdiff_formula         'C23 H17 N1 O1 P1 Cl1 Pd1'
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20), C21(H21), C22(H22),
  C23(H23)
;
_shelx_res_checksum              1221
_shelx_hkl_checksum              57959
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_completion    2014-06-02
_olex2_date_sample_data_collection 2014-06-02
_olex2_date_sample_submission    2014-05-16
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method
'The crystal was mounted on a MITIGEN holder in oil'
_olex2_submission_original_sample_id 'GR 83b'
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.160
_oxdiff_exptl_absorpt_empirical_full_min 0.484