Activation of diverse carbon-heteroatom and carbon-carbon bonds via palladium(ii)-catalysed beta-X elimination
Van T. Tran; John A. Gurak Jr; Kin S. Yang; Keary M. Engle; Nature Chemistry 10 (2018) 1126–1133; doi:10.1038/s41557-018-0110-z

data_1551413
_publ_section_title
;
 Activation of diverse carbon-heteroatom and carbon-carbon bonds via
 palladium(ii)-catalysed beta-X elimination
;
_journal_name_full               'Nature Chemistry'
_journal_page_first              1126
_journal_page_last               1133
_journal_paper_doi               10.1038/s41557-018-0110-z
_journal_volume                  10
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C21 H15 N3 O3 Pd'
_chemical_formula_sum            'C21 H15 N3 O3 Pd'
_chemical_formula_weight         463.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 112.945(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.0023(14)
_cell_length_b                   6.9693(9)
_cell_length_c                   17.7197(15)
_cell_measurement_reflns_used    5255
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.207
_cell_measurement_theta_min      2.495
_cell_volume                     1706.1(3)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       'APEX2 v2013.6-2 (Bruker, 2013)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX CCD'
_diffrn_detector_area_resol_mean 8.0
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15944
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.348
_diffrn_reflns_theta_min         2.496
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.118
_exptl_absorpt_correction_T_max  0.1525
_exptl_absorpt_correction_T_min  0.1201
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0531 before and 0.0456 after correction. The Ratio of minimum to maximum transmission is 0.7875. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.805
_exptl_crystal_description       needle
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.795
_refine_diff_density_min         -0.941
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.49(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     506
_refine_ls_number_reflns         6919
_refine_ls_number_restraints     536
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0461
_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/[\s^2^(Fo^2^)+(0.0539P)^2^+3.8998P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1095
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.994
_reflns_number_gt                6517
_reflns_number_total             6919
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            41557_2018_110_MOESM287_ESM.cif
_cod_data_source_block           engle55b_0m_b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the built-in table derived from the CIF
Core dictionary named 'cif_core.dic' version 2.4.5 last updated on
2014-11-21.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1551413
_shelx_estimated_absorpt_t_max   0.896
_shelx_estimated_absorpt_t_min   0.738
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.51(6)
 0.49(6)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
3. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4.a Ternary CH refined with riding coordinates:
 C12(H12), C12'(H12')
4.b Secondary CH2 refined with riding coordinates:
 C13(H13C,H13D), C11'(H11A,H11B), C11(H11C,H11D), C13'(H13A,H13B)
4.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C7'(H7'), C1(H1), C3'(H3'), C2'(H2'), C5(H5), C19(H19), C1'(H1'),
 C5'(H5'), C19'(H19'), C16'(H16'), C7(H7), C16(H16), C17(H17), C18'(H18'),
 C3(H3), C17'(H17'), C18(H18), C6'(H6'), C2(H2)
;
_shelx_res_checksum              97284
_shelx_hkl_checksum              56424