#------------------------------------------------------------------------------
#$Date: 2021-04-24 00:31:13 +0300 (Sat, 24 Apr 2021) $
#$Revision: 264486 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/86/4518622.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_4518622
loop_
_publ_author_name
'Huang, Jingjun'
'Isaac, Matthew'
'Watt, Ryan'
'Becica, Joseph'
'Dennis, Emma'
'Saidaminov, Makhsud I.'
'Sabbers, William A.'
'Leitch, David C.'
_publ_section_title
;
 DMPDAB--Pd--MAH: A Versatile Pd(0) Source for Precatalyst Formation,
 Reaction Screening, and Preparative-Scale Synthesis
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5636
_journal_page_last               5646
_journal_paper_doi               10.1021/acscatal.1c00288
_journal_year                    2021
_chemical_formula_moiety         'C22 H22 N2 O3 Pd'
_chemical_formula_sum            'C22 H22 N2 O3 Pd'
_chemical_formula_weight         468.81
_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
_audit_creation_date             2020-08-16
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                70.989(2)
_cell_angle_beta                 70.567(2)
_cell_angle_gamma                71.163(2)
_cell_formula_units_Z            2
_cell_length_a                   9.1137(9)
_cell_length_b                   10.2220(10)
_cell_length_c                   12.2985(12)
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.07
_cell_measurement_theta_min      2.44
_cell_volume                     991.53(17)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      99.96
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0136
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_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            16832
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.074
_diffrn_reflns_theta_min         1.811
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.961
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0483 before and 0.0227 after correction. The Ratio of minimum to maximum transmission is 0.9350. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.570
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.75
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.480
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         4746
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0171
_refine_ls_R_factor_gt           0.0162
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0199P)²+0.6548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0422
_refine_ls_wR_factor_ref         0.0427
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4591
_reflns_number_total             4746
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            cs1c00288_si_002.cif
_cod_data_source_block           1
_cod_database_code               4518622
_shelx_shelxl_version_number     2014/7
_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_max   0.910
_shelx_estimated_absorpt_t_min   0.533
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C20(H20), C19(H19)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), C5(H5), C6(H6), C15(H15), C7(H7), C17(H17), C16(H16)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C18(H18A,H18B,H18C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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 0.57171(2) 0.63312(2) 0.80380(2) 0.01041(3) Uani 1 1 d . . . . .
O2 O 0.22237(12) 0.71939(11) 0.76499(9) 0.0188(2) Uani 1 1 d . . . . .
O3 O 0.19192(14) 0.91099(12) 0.83017(12) 0.0292(3) Uani 1 1 d . . . . .
O1 O 0.26509(13) 0.49364(12) 0.75502(10) 0.0230(2) Uani 1 1 d . . . . .
N2 N 0.79625(13) 0.52927(12) 0.70243(10) 0.0123(2) Uani 1 1 d . . . . .
N1 N 0.72594(13) 0.76904(12) 0.76837(10) 0.0124(2) Uani 1 1 d . . . . .
C22 C 0.24889(16) 0.78613(15) 0.83816(13) 0.0185(3) Uani 1 1 d . . . . .
C20 C 0.37336(16) 0.54490(14) 0.88875(12) 0.0138(2) Uani 1 1 d . . . . .
H20 H 0.3801 0.4543 0.9526 0.017 Uiso 1 1 calc R . . . .
C2 C 0.91206(16) 0.58387(15) 0.68630(13) 0.0167(3) Uani 1 1 d . . . . .
H2 H 1.0193 0.5407 0.6509 0.020 Uiso 1 1 calc R . . . .
C1 C 0.87354(16) 0.71586(15) 0.72443(12) 0.0158(3) Uani 1 1 d . . . . .
H1 H 0.9550 0.7598 0.7167 0.019 Uiso 1 1 calc R . . . .
C4 C 0.92954(16) 0.27848(15) 0.69889(12) 0.0154(3) Uani 1 1 d . . . . .
C5 C 0.95339(17) 0.16473(15) 0.65060(13) 0.0183(3) Uani 1 1 d . . . . .
H5 H 1.0221 0.0756 0.6771 0.022 Uiso 1 1 calc R . . . .
C6 C 0.87829(17) 0.18017(15) 0.56472(13) 0.0186(3) Uani 1 1 d . . . . .
H6 H 0.8953 0.1016 0.5332 0.022 Uiso 1 1 calc R . . . .
C9 C 0.65223(18) 0.57039(15) 0.52076(13) 0.0190(3) Uani 1 1 d . . . . .
H9A H 0.5625 0.6006 0.5854 0.028 Uiso 1 1 calc GR . . . .
H9B H 0.6107 0.5643 0.4591 0.028 Uiso 1 1 calc GR . . . .
H9C H 0.7185 0.6399 0.4866 0.028 Uiso 1 1 calc GR . . . .
C8 C 0.75217(16) 0.42647(14) 0.56874(12) 0.0143(2) Uani 1 1 d . . . . .
C14 C 0.58008(17) 1.01633(15) 0.74295(13) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.34648(16) 0.67868(14) 0.91476(12) 0.0152(2) Uani 1 1 d . . . . .
H19 H 0.3317 0.6844 0.9975 0.018 Uiso 1 1 calc R . . . .
C12 C 0.73203(16) 0.90825(15) 0.89550(12) 0.0162(3) Uani 1 1 d . . . . .
C18 C 0.5317(2) 1.00583(16) 0.64094(14) 0.0237(3) Uani 1 1 d . . . . .
H18A H 0.4469 1.0899 0.6201 0.036 Uiso 1 1 calc GR . . . .
H18B H 0.4920 0.9197 0.6642 0.036 Uiso 1 1 calc GR . . . .
H18C H 0.6247 1.0010 0.5721 0.036 Uiso 1 1 calc GR . . . .
C15 C 0.53343(18) 1.14430(15) 0.77658(14) 0.0218(3) Uani 1 1 d . . . . .
H15 H 0.4653 1.2248 0.7377 0.026 Uiso 1 1 calc R . . . .
C3 C 0.82886(15) 0.40800(14) 0.65623(12) 0.0128(2) Uani 1 1 d . . . . .
C7 C 0.77807(17) 0.30995(15) 0.52417(12) 0.0172(3) Uani 1 1 d . . . . .
H7 H 0.7268 0.3191 0.4654 0.021 Uiso 1 1 calc R . . . .
C17 C 0.68277(18) 1.03897(16) 0.92539(13) 0.0213(3) Uani 1 1 d . . . . .
H17 H 0.7164 1.0483 0.9872 0.026 Uiso 1 1 calc R . . . .
C13 C 0.68069(16) 0.90050(14) 0.80288(12) 0.0136(2) Uani 1 1 d . . . . .
C21 C 0.28776(16) 0.57147(15) 0.79906(12) 0.0154(3) Uani 1 1 d . . . . .
C10 C 1.00682(18) 0.25762(16) 0.79630(14) 0.0210(3) Uani 1 1 d . . . . .
H10A H 1.0337 0.1560 0.8356 0.032 Uiso 1 1 calc GR . . . .
H10B H 0.9322 0.3106 0.8546 0.032 Uiso 1 1 calc GR . . . .
H10C H 1.1047 0.2927 0.7620 0.032 Uiso 1 1 calc GR . . . .
C11 C 0.82950(18) 0.78168(16) 0.96685(13) 0.0202(3) Uani 1 1 d . . . . .
H11A H 0.9423 0.7859 0.9386 0.030 Uiso 1 1 calc GR . . . .
H11B H 0.8196 0.6936 0.9573 0.030 Uiso 1 1 calc GR . . . .
H11C H 0.7900 0.7832 1.0510 0.030 Uiso 1 1 calc GR . . . .
C16 C 0.58572(19) 1.15501(16) 0.86629(15) 0.0243(3) Uani 1 1 d . . . . .
H16 H 0.5544 1.2434 0.8874 0.029 Uiso 1 1 calc R . . . .
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'
N N 0.0061 0.0033 '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'
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 76.30(4) . . ?
C20 Pd1 N2 124.67(5) . . ?
C20 Pd1 N1 157.61(5) . . ?
C19 Pd1 N2 164.64(5) . . ?
C19 Pd1 N1 117.93(5) . . ?
C19 Pd1 C20 40.42(5) . . ?
C22 O2 C21 108.65(11) . . ?
C2 N2 Pd1 113.36(9) . . ?
C2 N2 C3 118.58(11) . . ?
C3 N2 Pd1 128.03(8) . . ?
C1 N1 Pd1 114.08(9) . . ?
C1 N1 C13 119.67(11) . . ?
C13 N1 Pd1 125.75(9) . . ?
O2 C22 C19 108.48(11) . . ?
O3 C22 O2 119.52(14) . . ?
O3 C22 C19 131.99(15) . . ?
C19 C20 Pd1 68.61(7) . . ?
C19 C20 C21 107.01(11) . . ?
C21 C20 Pd1 106.96(9) . . ?
N2 C2 C1 117.65(12) . . ?
N1 C1 C2 117.22(12) . . ?
C5 C4 C3 117.57(13) . . ?
C5 C4 C10 120.03(12) . . ?
C3 C4 C10 122.37(12) . . ?
C6 C5 C4 120.87(13) . . ?
C5 C6 C7 120.45(13) . . ?
C3 C8 C9 120.55(12) . . ?
C7 C8 C9 121.54(12) . . ?
C7 C8 C3 117.84(12) . . ?
C15 C14 C18 120.86(13) . . ?
C15 C14 C13 117.70(13) . . ?
C13 C14 C18 121.34(13) . . ?
C22 C19 Pd1 104.94(9) . . ?
C20 C19 Pd1 70.96(8) . . ?
C20 C19 C22 107.11(12) . . ?
C17 C12 C13 117.36(13) . . ?
C17 C12 C11 119.35(13) . . ?
C13 C12 C11 123.22(13) . . ?
C16 C15 C14 120.45(14) . . ?
C4 C3 N2 121.02(12) . . ?
C4 C3 C8 122.60(12) . . ?
C8 C3 N2 116.37(11) . . ?
C6 C7 C8 120.67(13) . . ?
C16 C17 C12 120.85(14) . . ?
C14 C13 N1 117.05(12) . . ?
C12 C13 N1 120.19(12) . . ?
C12 C13 C14 122.73(12) . . ?
O2 C21 C20 108.41(11) . . ?
O1 C21 O2 119.20(13) . . ?
O1 C21 C20 132.38(13) . . ?
C17 C16 C15 120.89(13) . . ?
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 N2 2.1520(11) . ?
Pd1 N1 2.1342(11) . ?
Pd1 C20 2.0868(13) . ?
Pd1 C19 2.0556(14) . ?
O2 C22 1.4089(18) . ?
O2 C21 1.4101(17) . ?
O3 C22 1.1968(18) . ?
O1 C21 1.1959(17) . ?
N2 C2 1.2782(18) . ?
N2 C3 1.4341(16) . ?
N1 C1 1.2777(18) . ?
N1 C13 1.4329(16) . ?
C22 C19 1.4620(19) . ?
C20 C19 1.4315(18) . ?
C20 C21 1.4628(18) . ?
C2 C1 1.4697(19) . ?
C4 C5 1.3974(19) . ?
C4 C3 1.3976(18) . ?
C4 C10 1.5082(19) . ?
C5 C6 1.383(2) . ?
C6 C7 1.390(2) . ?
C9 C8 1.5063(18) . ?
C8 C3 1.4016(18) . ?
C8 C7 1.3902(19) . ?
C14 C18 1.506(2) . ?
C14 C15 1.393(2) . ?
C14 C13 1.4021(19) . ?
C12 C17 1.395(2) . ?
C12 C13 1.4001(19) . ?
C12 C11 1.507(2) . ?
C15 C16 1.385(2) . ?
C17 C16 1.381(2) . ?
