#------------------------------------------------------------------------------
#$Date: 2020-10-04 06:11:50 +0300 (Sun, 04 Oct 2020) $
#$Revision: 257065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/80/4518034.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_4518034
loop_
_publ_author_name
'Talukder, Md Muktadir'
'Cue, John Michael O.'
'Miller, Justin T.'
'Gamage, Prabhath L.'
'Aslam, Amina'
'McCandless, Gregory T.'
'Biewer, Michael C.'
'Stefan, Mihaela C.'
_publ_section_title
;
 Ligand Steric Effects of α-Diimine Nickel(II) and Palladium(II)
 Complexes in the Suzuki-Miyaura Cross-Coupling Reaction.
;
_journal_issue                   37
_journal_name_full               'ACS omega'
_journal_page_first              24018
_journal_page_last               24032
_journal_paper_doi               10.1021/acsomega.0c03415
_journal_volume                  5
_journal_year                    2020
_chemical_formula_moiety         'C16 H18 Cl2 N2 Pd'
_chemical_formula_sum            'C16 H18 Cl2 N2 Pd'
_chemical_formula_weight         415.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2019-06-05 # Formatted by publCIF

;
_cell_angle_alpha                112.209(10)
_cell_angle_beta                 107.067(9)
_cell_angle_gamma                96.813(10)
_cell_formula_units_Z            2
_cell_length_a                   8.623(3)
_cell_length_b                   9.493(3)
_cell_length_c                   11.552(4)
_cell_measurement_reflns_used    9833
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.54
_cell_measurement_theta_min      2.38
_cell_volume                     808.3(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXTL Intrinsic Phasing (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
;
Bruker Kappa D8 Quest CPAD diffractometer (with an Oxford Cryosystems cryostream
cooler)
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'HELIOS optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            25531
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.555
_diffrn_reflns_theta_min         2.383
_diffrn_source                   'I\mS microfocus tube'
_exptl_absorpt_coefficient_mu    1.472
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS (Krause, Herbst-Irmer, Sheldrick, & Stalke;  J. Appl. Cryst. 2015, 48,
3-10)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.708
_exptl_crystal_description       tablet
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.809
_refine_diff_density_min         -0.989
_refine_diff_density_rms         0.089
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4950
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0267
_refine_ls_R_factor_gt           0.0223
_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)+(0.0151P)²+0.8537P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0512
_refine_ls_wR_factor_ref         0.0543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4558
_reflns_number_total             4950
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ao0c03415_si_004.cif
_cod_data_source_block           scd2082_MMT_2M394
_cod_depositor_comments
'Adding full bibliography for 4518031--4518034.cif.'
_cod_original_cell_volume        808.2(4)
_cod_database_code               4518034
_publcif_datablock.id            {93b66e02-be72-4bad-9aac-6360b3268abd}
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.634
_shelx_estimated_absorpt_t_max   0.943
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1 Pd 0.52378(2) 0.47591(2) 0.83465(2) 0.01153(4) Uani 1 1 d . . . . .
Cl1 Cl 0.77529(5) 0.66278(5) 0.96242(4) 0.01689(8) Uani 1 1 d . . . . .
Cl2 Cl 0.40169(5) 0.65693(5) 0.78787(4) 0.01726(8) Uani 1 1 d . . . . .
N1 N 0.60720(18) 0.30033(16) 0.87338(14) 0.0122(3) Uani 1 1 d . . . . .
N2 N 0.30763(17) 0.29912(16) 0.72580(14) 0.0116(2) Uani 1 1 d . . . . .
C1 C 0.7620(2) 0.3010(2) 0.94095(18) 0.0150(3) Uani 1 1 d . . . . .
H1 H 0.852029 0.390212 0.971313 0.018 Uiso 1 1 calc R U . . .
C2 C 0.7957(2) 0.1744(2) 0.96841(18) 0.0165(3) Uani 1 1 d . . . . .
H2 H 0.907302 0.177743 1.016570 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6653(2) 0.0438(2) 0.92504(18) 0.0163(3) Uani 1 1 d . . . . .
H3 H 0.685744 -0.042353 0.944745 0.020 Uiso 1 1 calc R U . . .
C4 C 0.5035(2) 0.0414(2) 0.85183(18) 0.0163(3) Uani 1 1 d . . . . .
H4 H 0.412085 -0.047532 0.818979 0.020 Uiso 1 1 calc R U . . .
C5 C 0.4786(2) 0.17042(19) 0.82795(17) 0.0140(3) Uani 1 1 d . . . . .
C6 C 0.3169(2) 0.1768(2) 0.74796(18) 0.0153(3) Uani 1 1 d . . . . .
H6 H 0.219878 0.092374 0.712684 0.018 Uiso 1 1 calc R U . . .
C7 C 0.1471(2) 0.30746(19) 0.64818(17) 0.0130(3) Uani 1 1 d . . . . .
C8 C 0.0491(2) 0.3658(2) 0.72295(18) 0.0165(3) Uani 1 1 d . . . . .
H8 H 0.090474 0.396005 0.816997 0.020 Uiso 1 1 calc R U . . .
C9 C -0.1088(2) 0.3800(2) 0.6607(2) 0.0190(3) Uani 1 1 d . . . . .
H9 H -0.176334 0.418861 0.711145 0.023 Uiso 1 1 calc R U . . .
C10 C -0.1655(2) 0.3364(2) 0.5240(2) 0.0195(3) Uani 1 1 d . . . . .
H10 H -0.273144 0.345395 0.479810 0.023 Uiso 1 1 calc R U . . .
C11 C -0.0660(2) 0.2796(2) 0.45080(18) 0.0174(3) Uani 1 1 d . . . . .
H11 H -0.108154 0.251134 0.357052 0.021 Uiso 1 1 calc R U . . .
C12 C 0.0941(2) 0.26217(19) 0.50909(17) 0.0133(3) Uani 1 1 d . . . . .
C13 C 0.1968(2) 0.1973(2) 0.42102(18) 0.0152(3) Uani 1 1 d . . . . .
C14 C 0.1065(3) 0.1730(3) 0.2762(2) 0.0258(4) Uani 1 1 d . . . . .
H14A H 0.084960 0.272309 0.276938 0.039 Uiso 1 1 calc R U . . .
H14B H -0.000312 0.092463 0.235373 0.039 Uiso 1 1 calc R U . . .
H14C H 0.177328 0.138555 0.223789 0.039 Uiso 1 1 calc R U . . .
C15 C 0.3694(3) 0.3122(2) 0.4739(2) 0.0255(4) Uani 1 1 d . . . . .
H15A H 0.355086 0.417102 0.485857 0.038 Uiso 1 1 calc R U . . .
H15B H 0.424751 0.275269 0.409164 0.038 Uiso 1 1 calc R U . . .
H15C H 0.438650 0.317721 0.560361 0.038 Uiso 1 1 calc R U . . .
C16 C 0.2203(3) 0.0365(2) 0.4139(2) 0.0232(4) Uani 1 1 d . . . . .
H16A H 0.269927 -0.009670 0.346675 0.035 Uiso 1 1 calc R U . . .
H16B H 0.111013 -0.033883 0.388471 0.035 Uiso 1 1 calc R U . . .
H16C H 0.294965 0.050576 0.502007 0.035 Uiso 1 1 calc R U . . .
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'
Cl Cl 0.1484 0.1585 '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'
Pd Pd -0.9988 1.0072 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Pd1 N2 80.72(6) . . ?
N1 Pd1 Cl2 173.55(4) . . ?
N2 Pd1 Cl2 93.50(5) . . ?
N1 Pd1 Cl1 95.22(5) . . ?
N2 Pd1 Cl1 175.92(4) . . ?
Cl2 Pd1 Cl1 90.54(3) . . ?
C1 N1 C5 118.77(14) . . ?
C1 N1 Pd1 129.12(12) . . ?
C5 N1 Pd1 111.98(11) . . ?
C6 N2 C7 119.04(14) . . ?
C6 N2 Pd1 112.81(12) . . ?
C7 N2 Pd1 127.36(11) . . ?
N1 C1 C2 121.86(16) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.65(16) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.61(16) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.88(16) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N1 C5 C4 122.21(16) . . ?
N1 C5 C6 114.57(14) . . ?
C4 C5 C6 123.15(16) . . ?
N2 C6 C5 118.68(15) . . ?
N2 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
C8 C7 C12 122.68(16) . . ?
C8 C7 N2 114.34(15) . . ?
C12 C7 N2 122.98(15) . . ?
C9 C8 C7 120.40(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 118.67(17) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
C9 C10 C11 120.38(17) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 123.06(17) . . ?
C10 C11 H11 118.5 . . ?
C12 C11 H11 118.5 . . ?
C7 C12 C11 114.81(16) . . ?
C7 C12 C13 125.13(15) . . ?
C11 C12 C13 120.06(15) . . ?
C15 C13 C14 106.68(16) . . ?
C15 C13 C16 109.39(16) . . ?
C14 C13 C16 107.09(15) . . ?
C15 C13 C12 111.45(14) . . ?
C14 C13 C12 110.95(15) . . ?
C16 C13 C12 111.09(15) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 N1 2.0383(15) . ?
Pd1 N2 2.0392(15) . ?
Pd1 Cl2 2.2694(7) . ?
Pd1 Cl1 2.2929(8) . ?
N1 C1 1.332(2) . ?
N1 C5 1.368(2) . ?
N2 C6 1.286(2) . ?
N2 C7 1.441(2) . ?
C1 C2 1.395(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.386(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.452(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.395(2) . ?
C7 C12 1.406(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.382(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.391(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.407(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.543(2) . ?
C13 C15 1.535(3) . ?
C13 C14 1.536(3) . ?
C13 C16 1.539(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 -1.1(3) . . . . ?
Pd1 N1 C1 C2 174.38(13) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 C2 C3 C4 1.5(3) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C1 N1 C5 C4 1.1(3) . . . . ?
Pd1 N1 C5 C4 -175.08(14) . . . . ?
C1 N1 C5 C6 -176.12(15) . . . . ?
Pd1 N1 C5 C6 7.65(19) . . . . ?
C3 C4 C5 N1 0.1(3) . . . . ?
C3 C4 C5 C6 177.18(17) . . . . ?
C7 N2 C6 C5 -179.09(15) . . . . ?
Pd1 N2 C6 C5 -8.5(2) . . . . ?
N1 C5 C6 N2 0.6(2) . . . . ?
C4 C5 C6 N2 -176.67(17) . . . . ?
C6 N2 C7 C8 85.3(2) . . . . ?
Pd1 N2 C7 C8 -83.72(17) . . . . ?
C6 N2 C7 C12 -95.3(2) . . . . ?
Pd1 N2 C7 C12 95.70(18) . . . . ?
C12 C7 C8 C9 0.6(3) . . . . ?
N2 C7 C8 C9 -179.93(15) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C8 C7 C12 C11 -0.3(2) . . . . ?
N2 C7 C12 C11 -179.63(15) . . . . ?
C8 C7 C12 C13 179.85(16) . . . . ?
N2 C7 C12 C13 0.5(3) . . . . ?
C10 C11 C12 C7 -0.2(3) . . . . ?
C10 C11 C12 C13 179.66(16) . . . . ?
C7 C12 C13 C15 -56.6(2) . . . . ?
C11 C12 C13 C15 123.50(18) . . . . ?
C7 C12 C13 C14 -175.34(16) . . . . ?
C11 C12 C13 C14 4.8(2) . . . . ?
C7 C12 C13 C16 65.7(2) . . . . ?
C11 C12 C13 C16 -114.24(18) . . . . ?
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{93b66e02-be72-4bad-9aac-6360b3268abd} '_publcif_info_datablock.publ_exptl'
loop_
_publcif_info_cif.paper_type
EE
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{93b66e02-be72-4bad-9aac-6360b3268abd} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?
