#------------------------------------------------------------------------------
#$Date: 2021-06-05 20:58:16 +0300 (Sat, 05 Jun 2021) $
#$Revision: 265927 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/07/1560764.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_1560764
loop_
_publ_author_name
'Tóth, Balázs L.'
'Monory, Anna'
'Egyed, Orsolya'
'Domján, Attila'
'Bényei, Attila'
'Szathury, Bálint'
'Novák, Zoltán'
'Stirling, András'
_publ_section_title
;
 The ortho effect in directed C--H activation
;
_journal_issue                   14
_journal_name_full               'Chemical Science'
_journal_page_first              5152
_journal_page_last               5163
_journal_paper_doi               10.1039/D1SC00642H
_journal_volume                  12
_journal_year                    2021
_chemical_formula_moiety         'C17 H14 F3 N O4 Pd'
_chemical_formula_sum            'C17 H14 F3 N O4 Pd'
_chemical_formula_weight         459.69
_chemical_name_common            MA15
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2020-11-16 deposited with the CCDC.	2021-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 125.0080(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   20.9754(8)
_cell_length_b                   13.1973(6)
_cell_length_c                   15.3039(11)
_cell_measurement_reflns_used    154
_cell_measurement_temperature    295.00(10)
_cell_measurement_theta_max      25.4084
_cell_measurement_theta_min      5.1002
_cell_volume                     3469.9(3)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    Mercury
_computing_publication_material  'WinGX, PublCIF'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295.00(10)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and π scan'
_diffrn_radiation_monochromator  'multilayer mirror INCOATEC'
_diffrn_radiation_type           ' Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1244
_diffrn_reflns_av_unetI/netI     0.0745
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            48632
_diffrn_reflns_theta_full        25.72
_diffrn_reflns_theta_max         25.72
_diffrn_reflns_theta_min         2.71
_diffrn_source                   'microfocus sealed tube'
_diffrn_source_type              'INCOATEC I\mS 3.0'
_exptl_absorpt_coefficient_mu    1.122
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1824
_exptl_crystal_size_max          0.457
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.058
_refine_diff_density_max         0.743
_refine_diff_density_min         -0.490
_refine_ls_extinction_coef       0.00060(16)
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3279
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0978
_refine_ls_R_factor_gt           0.0504
_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/[σ²(Fo²)+(0.0478P)²+3.3885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0952
_reflns_number_gt                2460
_reflns_number_total             3279
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1sc00642h5.cif
_cod_data_source_block           45
_cod_depositor_comments
'Adding full bibliography for 1560759--1560764.cif.'
_cod_database_code               1560764
_publcif_datablock.id            {7e0f0dde-aae1-4714-b776-11369507ee8f}
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C10 0.6987(2) 0.4153(4) 0.5549(4) 0.0934(17) Uani d . . . 1 . .
H H10A 0.730892 0.364076 0.606277 0.14 Uiso calc U . R 1 . .
H H10B 0.702896 0.476841 0.591279 0.14 Uiso calc U . R 1 . .
H H10C 0.715461 0.42726 0.509148 0.14 Uiso calc U . R 1 . .
C C11 0.47658(18) 0.4304(3) 0.3708(3) 0.0438(8) Uani d . . . 1 . .
C C12 0.4382(2) 0.3401(3) 0.3613(3) 0.0486(9) Uani d . . . 1 . .
H H12 0.466518 0.283651 0.401175 0.058 Uiso calc U . R 1 . .
C C13 0.3582(2) 0.3349(3) 0.2926(3) 0.0523(9) Uani d . . . 1 . .
C C14 0.3163(2) 0.4190(3) 0.2332(3) 0.0669(12) Uani d . . . 1 . .
H H14 0.262489 0.414662 0.185516 0.08 Uiso calc U . R 1 . .
C C15 0.3532(2) 0.5083(3) 0.2439(4) 0.0666(12) Uani d . . . 1 . .
H H15 0.324083 0.564543 0.204329 0.08 Uiso calc U . R 1 . .
C C16 0.43362(19) 0.5159(3) 0.3132(3) 0.0488(9) Uani d . . . 1 . .
C C17 0.3546(3) 0.1669(4) 0.3467(4) 0.0790(14) Uani d . . . 1 . .
H H17A 0.317563 0.114973 0.331821 0.119 Uiso calc U . R 1 . .
H H17B 0.380397 0.18899 0.419221 0.119 Uiso calc U . R 1 . .
H H17C 0.392317 0.14037 0.336094 0.119 Uiso calc U . R 1 . .
C C20 0.56112(19) 0.4498(3) 0.4368(3) 0.0488(9) Uani d . . . 1 . .
C C21 0.60475(19) 0.2734(3) 0.4813(3) 0.0516(9) Uani d . . . 1 . .
C C22 0.6063(2) 0.2213(4) 0.5603(3) 0.0632(11) Uani d . . . 1 . .
H H22 0.616635 0.254944 0.620539 0.076 Uiso calc U . R 1 . .
C C23 0.5925(3) 0.1188(4) 0.5489(5) 0.0808(15) Uani d . . . 1 . .
H H23 0.592016 0.083192 0.600963 0.097 Uiso calc U . R 1 . .
C C24 0.5796(3) 0.0692(4) 0.4628(5) 0.0894(16) Uani d . . . 1 . .
H H24 0.5695 1.2e-05 0.455336 0.107 Uiso calc U . R 1 . .
C C25 0.5814(3) 0.1207(4) 0.3869(5) 0.0919(17) Uani d . . . 1 . .
H H25 0.574383 0.085999 0.329025 0.11 Uiso calc U . R 1 . .
C C26 0.5936(3) 0.2238(4) 0.3957(4) 0.0717(12) Uani d . . . 1 . .
H H26 0.594292 0.259179 0.343642 0.086 Uiso calc U . R 1 . .
C C40 0.3914(2) 0.7720(3) 0.1627(3) 0.0510(9) Uani d . . . 1 . .
C C41 0.3256(3) 0.8508(3) 0.1162(4) 0.0674(12) Uani d . . . 1 . .
O O1 0.58231(13) 0.54143(19) 0.4432(2) 0.0563(7) Uani d . . . 1 . .
O O3 0.31554(14) 0.2498(2) 0.2772(2) 0.0703(8) Uani d . . . 1 . .
O O41 0.40201(15) 0.7275(2) 0.2413(2) 0.0629(7) Uani d . . . 1 . .
O O42 0.57543(15) 0.7631(2) 0.3822(2) 0.0597(7) Uani d . . . 1 . .
F F41 0.3493(2) 0.9293(2) 0.1809(3) 0.1132(11) Uani d . . . 1 . .
F F42 0.30512(19) 0.8883(2) 0.0250(3) 0.1037(10) Uani d . . . 1 . .
F F43 0.26368(17) 0.8155(3) 0.1053(3) 0.1223(13) Uani d . . . 1 . .
Pd Pd1 0.49581(2) 0.63621(2) 0.34122(2) 0.05007(15) Uani d . . . 1 . .
N N1 0.61716(16) 0.3810(2) 0.4905(3) 0.0580(9) Uani d . . . 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 C10 H10A . . 109.5 ?
N1 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
N1 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C16 C11 C12 . . 119.9(3) ?
C16 C11 C20 . . 112.3(3) ?
C12 C11 C20 . . 127.8(3) ?
C13 C12 C11 . . 119.9(3) ?
C13 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
O3 C13 C12 . . 124.1(4) ?
O3 C13 C14 . . 116.0(3) ?
C12 C13 C14 . . 119.9(4) ?
C15 C14 C13 . . 120.7(4) ?
C15 C14 H14 . . 119.6 ?
C13 C14 H14 . . 119.6 ?
C14 C15 C16 . . 120.6(4) ?
C14 C15 H15 . . 119.7 ?
C16 C15 H15 . . 119.7 ?
C15 C16 C11 . . 119.0(3) ?
C15 C16 Pd1 . . 126.6(3) ?
C11 C16 Pd1 . . 114.4(2) ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
O1 C20 N1 . . 117.1(3) ?
O1 C20 C11 . . 116.6(3) ?
N1 C20 C11 . . 126.4(3) ?
C26 C21 C22 . . 120.8(4) ?
C26 C21 N1 . . 119.4(4) ?
C22 C21 N1 . . 119.8(4) ?
C23 C22 C21 . . 119.0(5) ?
C23 C22 H22 . . 120.5 ?
C21 C22 H22 . . 120.5 ?
C24 C23 C22 . . 120.7(5) ?
C24 C23 H23 . . 119.7 ?
C22 C23 H23 . . 119.7 ?
C23 C24 C25 . . 120.1(5) ?
C23 C24 H24 . . 120.0 ?
C25 C24 H24 . . 120.0 ?
C24 C25 C26 . . 120.2(5) ?
C24 C25 H25 . . 119.9 ?
C26 C25 H25 . . 119.9 ?
C21 C26 C25 . . 119.3(5) ?
C21 C26 H26 . . 120.4 ?
C25 C26 H26 . . 120.4 ?
O42 C40 O41 2_655 . 130.6(4) ?
O42 C40 C41 2_655 . 116.7(4) ?
O41 C40 C41 . . 112.6(4) ?
F43 C41 F42 . . 108.0(4) ?
F43 C41 F41 . . 107.3(4) ?
F42 C41 F41 . . 104.9(4) ?
F43 C41 C40 . . 112.5(3) ?
F42 C41 C40 . . 114.2(4) ?
F41 C41 C40 . . 109.4(4) ?
C20 O1 Pd1 . . 114.3(2) ?
C13 O3 C17 . . 117.8(3) ?
C40 O41 Pd1 . . 124.4(2) ?
C40 O42 Pd1 2_655 . 119.7(2) ?
C16 Pd1 O1 . . 81.69(12) ?
C16 Pd1 O41 . . 94.58(13) ?
O1 Pd1 O41 . . 175.09(10) ?
C16 Pd1 O42 . . 174.71(13) ?
O1 Pd1 O42 . . 93.05(10) ?
O41 Pd1 O42 . . 90.70(11) ?
C16 Pd1 Pd1 . 2_655 101.08(11) ?
O1 Pd1 Pd1 . 2_655 102.78(8) ?
O41 Pd1 Pd1 . 2_655 81.02(8) ?
O42 Pd1 Pd1 . 2_655 79.52(7) ?
C20 N1 C21 . . 124.6(3) ?
C20 N1 C10 . . 118.6(3) ?
C21 N1 C10 . . 116.4(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C10 N1 . 1.472(5) ?
C10 H10A . 0.96 ?
C10 H10B . 0.96 ?
C10 H10C . 0.96 ?
C11 C16 . 1.397(5) ?
C11 C12 . 1.399(5) ?
C11 C20 . 1.475(4) ?
C12 C13 . 1.378(5) ?
C12 H12 . 0.93 ?
C13 O3 . 1.370(4) ?
C13 C14 . 1.383(6) ?
C14 C15 . 1.368(6) ?
C14 H14 . 0.93 ?
C15 C16 . 1.389(5) ?
C15 H15 . 0.93 ?
C16 Pd1 . 1.940(4) ?
C17 O3 . 1.414(5) ?
C17 H17A . 0.96 ?
C17 H17B . 0.96 ?
C17 H17C . 0.96 ?
C20 O1 . 1.273(4) ?
C20 N1 . 1.331(4) ?
C21 C26 . 1.360(6) ?
C21 C22 . 1.374(6) ?
C21 N1 . 1.436(5) ?
C22 C23 . 1.373(6) ?
C22 H22 . 0.93 ?
C23 C24 . 1.353(7) ?
C23 H23 . 0.93 ?
C24 C25 . 1.365(8) ?
C24 H24 . 0.93 ?
C25 C26 . 1.377(7) ?
C25 H25 . 0.93 ?
C26 H26 . 0.93 ?
C40 O42 2_655 1.234(5) ?
C40 O41 . 1.238(5) ?
C40 C41 . 1.538(5) ?
C41 F43 . 1.297(5) ?
C41 F42 . 1.300(6) ?
C41 F41 . 1.318(5) ?
O1 Pd1 . 2.011(2) ?
O41 Pd1 . 2.051(3) ?
O42 Pd1 . 2.188(3) ?
Pd1 Pd1 2_655 2.8963(6) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C10 H10A O3 8_556 0.96 2.63 3.572(6) 166.6 ?
C22 H22 O41 5_666 0.93 2.37 3.212(5) 150.1 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C16 C11 C12 C13 . . . . 2.0(6) ?
C20 C11 C12 C13 . . . . -177.9(4) ?
C11 C12 C13 O3 . . . . 179.4(4) ?
C11 C12 C13 C14 . . . . 0.2(6) ?
O3 C13 C14 C15 . . . . 178.9(4) ?
C12 C13 C14 C15 . . . . -1.8(7) ?
C13 C14 C15 C16 . . . . 1.2(7) ?
C14 C15 C16 C11 . . . . 1.0(7) ?
C14 C15 C16 Pd1 . . . . -178.7(3) ?
C12 C11 C16 C15 . . . . -2.6(6) ?
C20 C11 C16 C15 . . . . 177.4(4) ?
C12 C11 C16 Pd1 . . . . 177.1(3) ?
C20 C11 C16 Pd1 . . . . -2.9(4) ?
C16 C11 C20 O1 . . . . 8.7(5) ?
C12 C11 C20 O1 . . . . -171.4(4) ?
C16 C11 C20 N1 . . . . -171.7(4) ?
C12 C11 C20 N1 . . . . 8.3(6) ?
C26 C21 C22 C23 . . . . -3.3(6) ?
N1 C21 C22 C23 . . . . 178.5(3) ?
C21 C22 C23 C24 . . . . 1.8(7) ?
C22 C23 C24 C25 . . . . 1.0(8) ?
C23 C24 C25 C26 . . . . -2.3(8) ?
C22 C21 C26 C25 . . . . 2.1(6) ?
N1 C21 C26 C25 . . . . -179.7(4) ?
C24 C25 C26 C21 . . . . 0.8(8) ?
O42 C40 C41 F43 2_655 . . . 133.3(4) ?
O41 C40 C41 F43 . . . . -46.8(6) ?
O42 C40 C41 F42 2_655 . . . 9.7(6) ?
O41 C40 C41 F42 . . . . -170.4(4) ?
O42 C40 C41 F41 2_655 . . . -107.6(5) ?
O41 C40 C41 F41 . . . . 72.3(5) ?
N1 C20 O1 Pd1 . . . . 170.3(3) ?
C11 C20 O1 Pd1 . . . . -10.0(4) ?
C12 C13 O3 C17 . . . . 9.4(6) ?
C14 C13 O3 C17 . . . . -171.4(4) ?
O42 C40 O41 Pd1 2_655 . . . 11.2(6) ?
C41 C40 O41 Pd1 . . . . -168.6(3) ?
O1 C20 N1 C21 . . . . -171.3(4) ?
C11 C20 N1 C21 . . . . 9.0(6) ?
O1 C20 N1 C10 . . . . 1.5(6) ?
C11 C20 N1 C10 . . . . -178.2(4) ?
C26 C21 N1 C20 . . . . 78.1(5) ?
C22 C21 N1 C20 . . . . -103.7(5) ?
C26 C21 N1 C10 . . . . -94.8(5) ?
C22 C21 N1 C10 . . . . 83.4(5) ?
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
l
