#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:48:29 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281612 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/83/1568374.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_1568374
loop_
_publ_author_name
'Shimomoto, Hiroaki'
'Miyano, Yuto'
'Kinoshita, Kaito'
'Itoh, Tomomichi'
'Ihara, Eiji'
_publ_section_title
;
 Initiating abilities of diphosphine- and diamine-ligated Pd
 complexes/NaBPh4 systems for C1 polymerization of diazoacetates
;
_journal_issue                   9
_journal_name_full               'Polymer Chemistry'
_journal_page_first              1007
_journal_page_last               1018
_journal_paper_doi               10.1039/D2PY01548J
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C17 H22 Br2 N2 O2 Pd'
_chemical_formula_sum            'C17 H22 Br2 N2 O2 Pd'
_chemical_formula_weight         552.58
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2022-07-20 deposited with the CCDC.	2023-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.286(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.3508(5)
_cell_length_b                   14.1078(5)
_cell_length_c                   10.6617(5)
_cell_measurement_reflns_used    10294
_cell_measurement_temperature    100
_cell_measurement_theta_max      31.2980
_cell_measurement_theta_min      1.9100
_cell_volume                     1821.80(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrystalClear-SM Expert 2.1 b46 (Rigaku, 2016)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 7.111
_diffrn_detector_type            'Rigaku Saturn724+ area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00   0.00  360
  2  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00  90.00  360
  3  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 180.00  360
  4  ω   -110.00  70.00   0.50    1.00    --  -20.00  45.00 270.00  360
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0051599000
_diffrn_orient_matrix_UB_12      0.0496104000
_diffrn_orient_matrix_UB_13      -0.0079831000
_diffrn_orient_matrix_UB_21      -0.0582388000
_diffrn_orient_matrix_UB_22      0.0047622000
_diffrn_orient_matrix_UB_23      -0.0104305000
_diffrn_orient_matrix_UB_31      0.0031730000
_diffrn_orient_matrix_UB_32      0.0066967000
_diffrn_orient_matrix_UB_33      0.0665551000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0780
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15542
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.948
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'MicroMax 007'
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.417
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.015
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.326
_refine_diff_density_min         -0.954
_refine_diff_density_rms         0.159
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         2293
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0483
_refine_ls_R_factor_gt           0.0379
_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/[σ²(Fo²)+(0.0534P)²+1.6127P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0942
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1924
_reflns_number_total             2293
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2py01548j2.cif
_cod_data_source_block           shimomoto_autored
_cod_depositor_comments
'Adding full bibliography for 1568372--1568378.cif.'
_cod_database_code               1568374
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         Pd1Br2O2N2C17H22
_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   0.899
_shelx_estimated_absorpt_t_min   0.854
_reflns_odcompleteness_completeness 94.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     31.07
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_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 2.104
_oxdiff_exptl_absorpt_empirical_full_min 0.766
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, 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 0.32947(3) 0.500000 0.78041(4) 0.01396(13) Uani 1 2 d S T P . .
Br1 Br 0.15760(3) 0.37917(3) 0.94375(4) 0.02657(14) Uani 1 1 d . . . . .
O1 O 0.1407(2) 0.30741(19) 0.6720(3) 0.0246(6) Uani 1 1 d . . . . .
N1 N 0.4449(3) 0.6137(2) 0.7640(3) 0.0175(7) Uani 1 1 d . . . . .
C4 C 0.1496(3) 0.3941(3) 0.6760(4) 0.0199(8) Uani 1 1 d . . . . .
C5 C 0.1750(3) 0.4483(3) 0.7951(4) 0.0184(8) Uani 1 1 d . . . . .
C3 C 0.1412(3) 0.4504(2) 0.5541(4) 0.0163(7) Uani 1 1 d . . . . .
C2 C 0.1308(3) 0.4019(3) 0.4395(4) 0.0219(8) Uani 1 1 d . . . . .
H2 H 0.130281 0.336013 0.439476 0.026 Uiso 1 1 calc R U . . .
C6 C 0.4122(3) 0.7009(3) 0.8257(4) 0.0214(8) Uani 1 1 d . . . . .
H6A H 0.338606 0.718759 0.785221 0.032 Uiso 1 1 calc R U . . .
H6B H 0.462314 0.751324 0.816903 0.032 Uiso 1 1 calc R U . . .
H6C H 0.414432 0.688867 0.914819 0.032 Uiso 1 1 calc R U . . .
C8 C 0.5611(3) 0.5912(3) 0.8230(4) 0.0201(8) Uani 1 1 d . . . . .
H8A H 0.566871 0.587750 0.914990 0.024 Uiso 1 1 calc R U . . .
H8B H 0.607244 0.643309 0.805852 0.024 Uiso 1 1 calc R U . . .
C7 C 0.4356(3) 0.6355(3) 0.6261(4) 0.0234(9) Uani 1 1 d . . . . .
H7A H 0.450422 0.579279 0.581609 0.035 Uiso 1 1 calc R U . . .
H7B H 0.488078 0.683752 0.616214 0.035 Uiso 1 1 calc R U . . .
H7C H 0.362343 0.657533 0.591408 0.035 Uiso 1 1 calc R U . . .
C1 C 0.1210(3) 0.4504(3) 0.3247(4) 0.0223(8) Uani 1 1 d . . . . .
H1 H 0.114543 0.417235 0.248263 0.027 Uiso 1 1 calc R U . . .
C9 C 0.6071(4) 0.500000 0.7788(6) 0.0221(12) Uani 1 2 d S T P . .
H9A H 0.593315 0.499999 0.686070 0.026 Uiso 1 2 calc R U P . .
H9B H 0.686555 0.500000 0.808657 0.026 Uiso 1 2 calc R U P . .
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'
Br Br -0.2901 2.4595 '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 N1 95.00(16) 6_565 . ?
C5 Pd1 N1 111.90(13) 6_565 . ?
C5 Pd1 N1 153.02(13) 6_565 6_565 ?
C5 Pd1 N1 111.90(13) . 6_565 ?
C5 Pd1 N1 153.02(13) . . ?
C5 Pd1 C5 41.1(2) . 6_565 ?
C6 N1 Pd1 109.6(2) . . ?
C8 N1 Pd1 113.8(2) . . ?
C8 N1 C6 108.3(3) . . ?
C8 N1 C7 110.2(3) . . ?
C7 N1 Pd1 107.9(2) . . ?
C7 N1 C6 106.9(3) . . ?
O1 C4 C5 123.6(4) . . ?
O1 C4 C3 120.3(4) . . ?
C5 C4 C3 116.1(3) . . ?
Br1 C5 Pd1 119.78(18) . . ?
C4 C5 Pd1 99.3(2) . . ?
C4 C5 Br1 114.5(3) . . ?
C5 C5 Pd1 69.43(10) 6_565 . ?
C5 C5 Br1 120.72(11) 6_565 . ?
C5 C5 C4 121.5(2) 6_565 . ?
C3 C3 C4 121.8(2) 6_565 . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 C3 119.6(2) . 6_565 ?
C3 C2 H2 119.6 . . ?
C3 C2 C1 120.8(4) . . ?
C1 C2 H2 119.6 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C8 H8A 108.3 . . ?
N1 C8 H8B 108.3 . . ?
N1 C8 C9 116.1(3) . . ?
H8A C8 H8B 107.4 . . ?
C9 C8 H8A 108.3 . . ?
C9 C8 H8B 108.3 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C2 C1 C1 119.6(2) . 6_565 ?
C2 C1 H1 120.2 . . ?
C1 C1 H1 120.2 6_565 . ?
C8 C9 C8 115.8(4) 6_565 . ?
C8 C9 H9A 108.3 6_565 . ?
C8 C9 H9A 108.3 . . ?
C8 C9 H9B 108.3 6_565 . ?
C8 C9 H9B 108.3 . . ?
H9A C9 H9B 107.4 . . ?
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 2.175(3) 6_565 ?
Pd1 N1 2.175(3) . ?
Pd1 C5 2.077(3) 6_565 ?
Pd1 C5 2.077(3) . ?
Br1 C5 1.908(4) . ?
O1 C4 1.228(4) . ?
N1 C6 1.488(5) . ?
N1 C8 1.484(5) . ?
N1 C7 1.484(5) . ?
C4 C5 1.463(6) . ?
C4 C3 1.509(5) . ?
C5 C5 1.460(7) 6_565 ?
C3 C3 1.399(7) 6_565 ?
C3 C2 1.384(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.386(6) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.519(5) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C1 C1 1.399(8) 6_565 ?
C1 H1 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
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
Pd1 N1 C8 C9 53.8(4) . . . . ?
O1 C4 C5 Pd1 114.0(3) . . . . ?
O1 C4 C5 Br1 -14.9(5) . . . . ?
O1 C4 C5 C5 -174.4(3) . . . 6_565 ?
O1 C4 C3 C3 174.3(2) . . . 6_565 ?
O1 C4 C3 C2 -4.2(5) . . . . ?
N1 C8 C9 C8 -70.6(6) . . . 6_565 ?
C4 C3 C2 C1 179.0(3) . . . . ?
C5 C4 C3 C3 -9.2(4) . . . 6_565 ?
C5 C4 C3 C2 172.2(3) . . . . ?
C3 C4 C5 Pd1 -62.3(3) . . . . ?
C3 C4 C5 Br1 168.8(2) . . . . ?
C3 C4 C5 C5 9.2(4) . . . 6_565 ?
C3 C3 C2 C1 0.4(4) 6_565 . . . ?
C3 C2 C1 C1 -0.4(4) . . . 6_565 ?
C6 N1 C8 C9 175.9(3) . . . . ?
C7 N1 C8 C9 -67.5(4) . . . . ?
