#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:07:40 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180169 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/65/7106553.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_7106553
loop_
_publ_author_name
'Alejandro Bugarin'
'Brian T. Connell'
_publ_section_title
;
 A highly active and selective palladium pincer catalyst for the formation
 of ?-aryl ketones via cross-coupling
;
_journal_name_full               Chem.Commun.
_journal_page_first              7218
_journal_paper_doi               10.1039/c1cc12071a
_journal_volume                  47
_journal_year                    2011
_chemical_formula_sum            'C20 H27 Br N2 O2 Pd'
_chemical_formula_weight         513.75
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 103.716(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6447(12)
_cell_length_b                   21.628(2)
_cell_length_c                   15.6491(15)
_cell_measurement_reflns_used    9541
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      62.21
_cell_measurement_theta_min      4.06
_cell_volume                     4157.7(7)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_sigmaI/netI    0.0276
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            74692
_diffrn_reflns_theta_full        60.00
_diffrn_reflns_theta_max         60.00
_diffrn_reflns_theta_min         4.14
_exptl_absorpt_coefficient_mu    9.576
_exptl_absorpt_correction_T_max  0.9103
_exptl_absorpt_correction_T_min  0.1897
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'yellow '
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'needle '
_exptl_crystal_F_000             2064
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.729
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     514
_refine_ls_number_reflns         6004
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.009
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0311
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0330P)²+8.8000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0690
_refine_ls_wR_factor_ref         0.0707
_reflns_number_gt                5333
_reflns_number_total             6004
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c1cc12071a.txt
_cod_data_source_block           bc
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7106553
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Pd1A Pd 0.08881(2) 0.852027(13) 0.236112(19) 0.02354(9) Uani 1 1 d . . .
Br1A Br 0.12789(4) 0.96564(2) 0.22137(3) 0.03868(13) Uani 1 1 d . . .
O1A O 0.3442(2) 0.72929(12) 0.29557(18) 0.0259(6) Uani 1 1 d . . .
O2A O -0.2182(2) 0.80078(16) 0.2544(2) 0.0419(8) Uani 1 1 d . . .
N1A N 0.2428(3) 0.81381(15) 0.2507(2) 0.0232(7) Uani 1 1 d . . .
N2A N -0.0755(3) 0.85541(17) 0.2346(2) 0.0286(8) Uani 1 1 d . . .
C1A C 0.3566(3) 0.83606(19) 0.2603(3) 0.0282(10) Uani 1 1 d . . .
C2A C 0.4197(3) 0.7749(2) 0.2745(3) 0.0313(10) Uani 1 1 d . . .
H2AA H 0.4426 0.7628 0.2206 0.038 Uiso 1 1 calc R . .
H2AB H 0.4853 0.7787 0.3235 0.038 Uiso 1 1 calc R . .
C3A C 0.2467(3) 0.75652(18) 0.2745(2) 0.0217(9) Uani 1 1 d . . .
C4A C 0.1467(3) 0.72537(18) 0.2821(3) 0.0235(9) Uani 1 1 d . . .
C5A C 0.1314(3) 0.66704(19) 0.3126(3) 0.0242(9) Uani 1 1 d . . .
H5AA H 0.1909 0.6390 0.3262 0.029 Uiso 1 1 calc R . .
C6A C 0.0295(3) 0.64865(19) 0.3239(3) 0.0256(9) Uani 1 1 d . . .
C7A C -0.0577(3) 0.6910(2) 0.3013(3) 0.0298(10) Uani 1 1 d . . .
H7AA H -0.1280 0.6795 0.3076 0.036 Uiso 1 1 calc R . .
C8A C -0.0412(3) 0.74926(19) 0.2702(3) 0.0252(9) Uani 1 1 d . . .
C9A C 0.0604(3) 0.76663(19) 0.2605(3) 0.0253(9) Uani 1 1 d . . .
C10A C -0.1142(3) 0.8029(2) 0.2523(3) 0.0320(11) Uani 1 1 d . . .
C11A C -0.2604(4) 0.8627(2) 0.2343(4) 0.0483(13) Uani 1 1 d . . .
H11A H -0.2934 0.8783 0.2816 0.058 Uiso 1 1 calc R . .
H11B H -0.3165 0.8632 0.1781 0.058 Uiso 1 1 calc R . .
C12A C -0.1610(4) 0.9032(2) 0.2272(3) 0.0359(11) Uani 1 1 d . . .
C13A C 0.0118(3) 0.58605(19) 0.3645(3) 0.0319(10) Uani 1 1 d D . .
C14A C -0.0135(5) 0.5967(3) 0.4530(3) 0.0673(19) Uani 1 1 d D . .
H14A H -0.0775 0.6234 0.4458 0.101 Uiso 1 1 calc R . .
H14B H 0.0489 0.6165 0.4927 0.101 Uiso 1 1 calc R . .
H14C H -0.0283 0.5569 0.4779 0.101 Uiso 1 1 calc R . .
C15A C -0.0786(4) 0.5499(3) 0.3016(4) 0.071(2) Uani 1 1 d D . .
H15A H -0.1468 0.5733 0.2916 0.107 Uiso 1 1 calc R . .
H15B H -0.0883 0.5097 0.3275 0.107 Uiso 1 1 calc R . .
H15C H -0.0586 0.5437 0.2454 0.107 Uiso 1 1 calc R . .
C16A C 0.1139(4) 0.5442(2) 0.3797(3) 0.0426(12) Uani 1 1 d D . .
H16A H 0.1747 0.5647 0.4203 0.064 Uiso 1 1 calc R . .
H16B H 0.1331 0.5368 0.3235 0.064 Uiso 1 1 calc R . .
H16C H 0.0985 0.5047 0.4048 0.064 Uiso 1 1 calc R . .
C17A C 0.3853(4) 0.8775(2) 0.3416(3) 0.0459(13) Uani 1 1 d . . .
H17A H 0.3364 0.9133 0.3331 0.069 Uiso 1 1 calc R . .
H17B H 0.4608 0.8917 0.3504 0.069 Uiso 1 1 calc R . .
H17C H 0.3773 0.8541 0.3933 0.069 Uiso 1 1 calc R . .
C18A C 0.3706(4) 0.8691(2) 0.1787(3) 0.0408(12) Uani 1 1 d . . .
H18A H 0.3426 0.8430 0.1271 0.061 Uiso 1 1 calc R . .
H18B H 0.4480 0.8775 0.1839 0.061 Uiso 1 1 calc R . .
H18C H 0.3302 0.9082 0.1722 0.061 Uiso 1 1 calc R . .
C19A C -0.1774(5) 0.9368(3) 0.1398(3) 0.0573(16) Uani 1 1 d . . .
H19A H -0.1088 0.9561 0.1354 0.086 Uiso 1 1 calc R . .
H19B H -0.2332 0.9688 0.1361 0.086 Uiso 1 1 calc R . .
H19C H -0.2008 0.9072 0.0915 0.086 Uiso 1 1 calc R . .
C20A C -0.1292(5) 0.9477(2) 0.3038(3) 0.0476(13) Uani 1 1 d . . .
H20A H -0.0639 0.9706 0.2993 0.071 Uiso 1 1 calc R . .
H20B H -0.1141 0.9245 0.3592 0.071 Uiso 1 1 calc R . .
H20C H -0.1890 0.9768 0.3026 0.071 Uiso 1 1 calc R . .
Pd1B Pd 0.61117(2) 0.765521(13) 0.516961(19) 0.02119(9) Uani 1 1 d . . .
Br1B Br 0.78746(4) 0.74768(2) 0.47351(4) 0.04863(16) Uani 1 1 d . . .
O1B O 0.3747(2) 0.63107(13) 0.46293(19) 0.0331(7) Uani 1 1 d . . .
O2B O 0.5465(2) 0.93763(13) 0.60532(19) 0.0313(7) Uani 1 1 d . . .
N1B N 0.5328(3) 0.68206(15) 0.4803(2) 0.0253(8) Uani 1 1 d . . .
N2B N 0.6300(3) 0.85639(15) 0.5614(2) 0.0243(8) Uani 1 1 d . . .
C1B C 0.5555(4) 0.62197(19) 0.4406(3) 0.0294(10) Uani 1 1 d . . .
C2B C 0.4546(4) 0.5848(2) 0.4471(4) 0.0444(13) Uani 1 1 d . . .
H2BA H 0.4250 0.5620 0.3918 0.053 Uiso 1 1 calc R . .
H2BB H 0.4726 0.5549 0.4962 0.053 Uiso 1 1 calc R . .
C3B C 0.4330(3) 0.68255(19) 0.4873(3) 0.0252(9) Uani 1 1 d . . .
C4B C 0.3901(3) 0.73728(19) 0.5199(2) 0.0245(9) Uani 1 1 d . . .
C5B C 0.2854(3) 0.7514(2) 0.5285(3) 0.0283(10) Uani 1 1 d . A .
H5BA H 0.2299 0.7209 0.5140 0.034 Uiso 1 1 calc R . .
C6B C 0.2606(3) 0.8094(2) 0.5579(3) 0.0296(10) Uani 1 1 d . . .
C7B C 0.3442(3) 0.8536(2) 0.5787(3) 0.0307(10) Uani 1 1 d . A .
H7BA H 0.3277 0.8934 0.5979 0.037 Uiso 1 1 calc R . .
C8B C 0.4488(3) 0.84173(18) 0.5724(2) 0.0181(8) Uani 1 1 d . . .
C9B C 0.4716(3) 0.78171(18) 0.5412(2) 0.0208(9) Uani 1 1 d . A .
C10B C 0.5439(3) 0.87849(19) 0.5805(3) 0.0258(9) Uani 1 1 d . A .
C11B C 0.6565(4) 0.9594(2) 0.6064(3) 0.0372(11) Uani 1 1 d . . .
H11C H 0.6959 0.9705 0.6670 0.045 Uiso 1 1 calc R . .
H11D H 0.6533 0.9963 0.5684 0.045 Uiso 1 1 calc R . .
C12B C 0.7135(3) 0.90599(19) 0.5715(3) 0.0284(10) Uani 1 1 d . . .
C13B C 0.1448(3) 0.8267(2) 0.5625(3) 0.0359(11) Uani 0.555(9) 1 d PD A 1
C14B C 0.1041(9) 0.8756(5) 0.4943(6) 0.076(5) Uani 0.555(9) 1 d PD A 1
H14D H 0.1533 0.9113 0.5052 0.114 Uiso 0.555(9) 1 calc PR A 1
H14E H 0.0309 0.8887 0.4976 0.114 Uiso 0.555(9) 1 calc PR A 1
H14F H 0.1015 0.8589 0.4357 0.114 Uiso 0.555(9) 1 calc PR A 1
C15B C 0.1469(7) 0.8467(5) 0.6562(4) 0.044(3) Uani 0.555(9) 1 d PD A 1
H15D H 0.1925 0.8836 0.6710 0.066 Uiso 0.555(9) 1 calc PR A 1
H15E H 0.1768 0.8132 0.6970 0.066 Uiso 0.555(9) 1 calc PR A 1
H15F H 0.0727 0.8561 0.6609 0.066 Uiso 0.555(9) 1 calc PR A 1
C16B C 0.0698(7) 0.7695(4) 0.5423(7) 0.072(4) Uani 0.555(9) 1 d PD A 1
H16D H -0.0036 0.7807 0.5472 0.109 Uiso 0.555(9) 1 calc PR A 1
H16E H 0.0985 0.7365 0.5844 0.109 Uiso 0.555(9) 1 calc PR A 1
H16F H 0.0669 0.7550 0.4825 0.109 Uiso 0.555(9) 1 calc PR A 1
C13' C 0.1448(3) 0.8267(2) 0.5625(3) 0.0359(11) Uani 0.445(9) 1 d PD A 2
C14' C 0.0704(7) 0.8250(5) 0.4708(4) 0.034(3) Uani 0.445(9) 1 d PD A 2
H14G H 0.0938 0.8563 0.4339 0.051 Uiso 0.445(9) 1 calc PR A 2
H14H H -0.0046 0.8335 0.4743 0.051 Uiso 0.445(9) 1 calc PR A 2
H14I H 0.0739 0.7840 0.4450 0.051 Uiso 0.445(9) 1 calc PR A 2
C15' C 0.1346(8) 0.8901(4) 0.6055(8) 0.052(4) Uani 0.445(9) 1 d PD A 2
H15G H 0.1577 0.9229 0.5707 0.078 Uiso 0.445(9) 1 calc PR A 2
H15H H 0.1809 0.8906 0.6653 0.078 Uiso 0.445(9) 1 calc PR A 2
H15I H 0.0587 0.8970 0.6077 0.078 Uiso 0.445(9) 1 calc PR A 2
C16' C 0.0981(7) 0.7800(4) 0.6194(6) 0.040(3) Uani 0.445(9) 1 d PD A 2
H16G H 0.1038 0.7380 0.5976 0.060 Uiso 0.445(9) 1 calc PR A 2
H16H H 0.0215 0.7897 0.6159 0.060 Uiso 0.445(9) 1 calc PR A 2
H16I H 0.1395 0.7828 0.6807 0.060 Uiso 0.445(9) 1 calc PR A 2
C17B C 0.6586(4) 0.5925(2) 0.4947(3) 0.0374(11) Uani 1 1 d . . .
H17D H 0.6539 0.5893 0.5561 0.056 Uiso 1 1 calc R . .
H17E H 0.7214 0.6181 0.4912 0.056 Uiso 1 1 calc R . .
H17F H 0.6672 0.5512 0.4716 0.056 Uiso 1 1 calc R . .
C18B C 0.5621(4) 0.6324(2) 0.3458(3) 0.0343(11) Uani 1 1 d . . .
H18D H 0.6201 0.6621 0.3444 0.051 Uiso 1 1 calc R . .
H18E H 0.4924 0.6486 0.3117 0.051 Uiso 1 1 calc R . .
H18F H 0.5780 0.5931 0.3203 0.051 Uiso 1 1 calc R . .
C19B C 0.7333(5) 0.9206(2) 0.4809(4) 0.0558(15) Uani 1 1 d . . .
H19D H 0.7553 0.8828 0.4552 0.084 Uiso 1 1 calc R . .
H19E H 0.7911 0.9516 0.4870 0.084 Uiso 1 1 calc R . .
H19F H 0.6662 0.9367 0.4425 0.084 Uiso 1 1 calc R . .
C20B C 0.8165(4) 0.8855(2) 0.6363(3) 0.0419(12) Uani 1 1 d . . .
H20D H 0.8484 0.8503 0.6119 0.063 Uiso 1 1 calc R . .
H20E H 0.7991 0.8732 0.6917 0.063 Uiso 1 1 calc R . .
H20F H 0.8687 0.9198 0.6473 0.063 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd 0.1215 3.9337 '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
C9A Pd1A N2A 78.69(16) . . ?
C9A Pd1A N1A 79.14(15) . . ?
N2A Pd1A N1A 157.79(13) . . ?
C9A Pd1A Br1A 173.96(11) . . ?
N2A Pd1A Br1A 100.47(10) . . ?
N1A Pd1A Br1A 101.43(9) . . ?
C3A O1A C2A 105.1(3) . . ?
C10A O2A C11A 106.2(4) . . ?
C3A N1A C1A 108.1(3) . . ?
C3A N1A Pd1A 112.6(3) . . ?
C1A N1A Pd1A 137.7(3) . . ?
C10A N2A C12A 108.9(4) . . ?
C10A N2A Pd1A 113.3(3) . . ?
C12A N2A Pd1A 137.5(3) . . ?
N1A C1A C18A 111.8(3) . . ?
N1A C1A C17A 107.8(4) . . ?
C18A C1A C17A 112.0(4) . . ?
N1A C1A C2A 101.1(3) . . ?
C18A C1A C2A 111.7(4) . . ?
C17A C1A C2A 111.9(4) . . ?
O1A C2A C1A 105.6(3) . . ?
O1A C2A H2AA 110.6 . . ?
C1A C2A H2AA 110.6 . . ?
O1A C2A H2AB 110.6 . . ?
C1A C2A H2AB 110.6 . . ?
H2AA C2A H2AB 108.7 . . ?
N1A C3A O1A 117.7(4) . . ?
N1A C3A C4A 119.4(4) . . ?
O1A C3A C4A 122.9(3) . . ?
C5A C4A C9A 120.4(4) . . ?
C5A C4A C3A 130.1(4) . . ?
C9A C4A C3A 109.2(4) . . ?
C4A C5A C6A 120.9(4) . . ?
C4A C5A H5AA 119.6 . . ?
C6A C5A H5AA 119.6 . . ?
C5A C6A C7A 118.2(4) . . ?
C5A C6A C13A 122.2(4) . . ?
C7A C6A C13A 119.6(4) . . ?
C8A C7A C6A 120.3(4) . . ?
C8A C7A H7AA 119.9 . . ?
C6A C7A H7AA 119.9 . . ?
C9A C8A C7A 120.6(4) . . ?
C9A C8A C10A 108.9(4) . . ?
C7A C8A C10A 130.2(4) . . ?
C8A C9A C4A 119.8(4) . . ?
C8A C9A Pd1A 120.1(3) . . ?
C4A C9A Pd1A 119.3(3) . . ?
N2A C10A O2A 117.6(4) . . ?
N2A C10A C8A 118.8(4) . . ?
O2A C10A C8A 123.5(4) . . ?
O2A C11A C12A 105.9(4) . . ?
O2A C11A H11A 110.6 . . ?
C12A C11A H11A 110.6 . . ?
O2A C11A H11B 110.6 . . ?
C12A C11A H11B 110.6 . . ?
H11A C11A H11B 108.7 . . ?
N2A C12A C20A 109.2(4) . . ?
N2A C12A C19A 110.2(4) . . ?
C20A C12A C19A 111.2(4) . . ?
N2A C12A C11A 100.9(4) . . ?
C20A C12A C11A 111.6(4) . . ?
C19A C12A C11A 113.1(4) . . ?
C14A C13A C15A 112.2(4) . . ?
C14A C13A C6A 109.2(4) . . ?
C15A C13A C6A 110.1(3) . . ?
C14A C13A C16A 107.3(4) . . ?
C15A C13A C16A 105.6(4) . . ?
C6A C13A C16A 112.4(3) . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C13A C16A H16A 109.5 . . ?
C13A C16A H16B 109.5 . . ?
H16A C16A H16B 109.5 . . ?
C13A C16A H16C 109.5 . . ?
H16A C16A H16C 109.5 . . ?
H16B C16A H16C 109.5 . . ?
C1A C17A H17A 109.5 . . ?
C1A C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C1A C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C1A C18A H18A 109.5 . . ?
C1A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C1A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C12A C19A H19A 109.5 . . ?
C12A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C12A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C12A C20A H20A 109.5 . . ?
C12A C20A H20B 109.5 . . ?
H20A C20A H20B 109.5 . . ?
C12A C20A H20C 109.5 . . ?
H20A C20A H20C 109.5 . . ?
H20B C20A H20C 109.5 . . ?
C9B Pd1B N1B 79.18(15) . . ?
C9B Pd1B N2B 78.46(14) . . ?
N1B Pd1B N2B 157.61(13) . . ?
C9B Pd1B Br1B 175.54(11) . . ?
N1B Pd1B Br1B 100.85(10) . . ?
N2B Pd1B Br1B 101.36(9) . . ?
C3B O1B C2B 104.9(3) . . ?
C10B O2B C11B 105.7(3) . . ?
C3B N1B C1B 109.2(3) . . ?
C3B N1B Pd1B 112.5(3) . . ?
C1B N1B Pd1B 138.1(3) . . ?
C10B N2B C12B 109.0(3) . . ?
C10B N2B Pd1B 113.1(3) . . ?
C12B N2B Pd1B 137.7(3) . . ?
N1B C1B C17B 110.9(3) . . ?
N1B C1B C18B 109.7(3) . . ?
C17B C1B C18B 111.5(4) . . ?
N1B C1B C2B 100.5(3) . . ?
C17B C1B C2B 111.3(4) . . ?
C18B C1B C2B 112.4(4) . . ?
O1B C2B C1B 105.6(3) . . ?
O1B C2B H2BA 110.6 . . ?
C1B C2B H2BA 110.6 . . ?
O1B C2B H2BB 110.6 . . ?
C1B C2B H2BB 110.6 . . ?
H2BA C2B H2BB 108.8 . . ?
N1B C3B O1B 116.9(4) . . ?
N1B C3B C4B 119.5(4) . . ?
O1B C3B C4B 123.6(4) . . ?
C9B C4B C5B 119.5(4) . . ?
C9B C4B C3B 109.3(4) . . ?
C5B C4B C3B 131.1(4) . . ?
C4B C5B C6B 121.3(4) . . ?
C4B C5B H5BA 119.3 . . ?
C6B C5B H5BA 119.3 . . ?
C5B C6B C7B 118.2(4) . . ?
C5B C6B C13B 121.8(4) . . ?
C7B C6B C13B 119.8(4) . . ?
C8B C7B C6B 122.6(4) . . ?
C8B C7B H7BA 118.7 . . ?
C6B C7B H7BA 118.7 . . ?
C7B C8B C10B 134.2(4) . . ?
C7B C8B C9B 117.9(4) . . ?
C10B C8B C9B 107.4(3) . . ?
C4B C9B C8B 120.4(4) . . ?
C4B C9B Pd1B 119.3(3) . . ?
C8B C9B Pd1B 119.9(3) . . ?
N2B C10B O2B 117.4(4) . . ?
N2B C10B C8B 121.1(4) . . ?
O2B C10B C8B 121.5(4) . . ?
O2B C11B C12B 106.2(3) . . ?
O2B C11B H11C 110.5 . . ?
C12B C11B H11C 110.5 . . ?
O2B C11B H11D 110.5 . . ?
C12B C11B H11D 110.5 . . ?
H11C C11B H11D 108.7 . . ?
N2B C12B C20B 109.7(3) . . ?
N2B C12B C19B 108.5(4) . . ?
C20B C12B C19B 112.1(4) . . ?
N2B C12B C11B 101.6(3) . . ?
C20B C12B C11B 112.7(4) . . ?
C19B C12B C11B 111.7(4) . . ?
C14B C13B C15B 114.1(5) . . ?
C14B C13B C6B 108.0(5) . . ?
C15B C13B C6B 108.4(4) . . ?
C14B C13B C16B 109.2(5) . . ?
C15B C13B C16B 107.1(5) . . ?
C6B C13B C16B 110.0(5) . . ?
H14G C14' H14H 109.5 . . ?
H14G C14' H14I 109.5 . . ?
H14H C14' H14I 109.5 . . ?
H15G C15' H15H 109.5 . . ?
H15G C15' H15I 109.5 . . ?
H15H C15' H15I 109.5 . . ?
H16G C16' H16H 109.5 . . ?
H16G C16' H16I 109.5 . . ?
H16H C16' H16I 109.5 . . ?
C1B C17B H17D 109.5 . . ?
C1B C17B H17E 109.5 . . ?
H17D C17B H17E 109.5 . . ?
C1B C17B H17F 109.5 . . ?
H17D C17B H17F 109.5 . . ?
H17E C17B H17F 109.5 . . ?
C1B C18B H18D 109.5 . . ?
C1B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C1B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
C12B C19B H19D 109.5 . . ?
C12B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C12B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?
C12B C20B H20D 109.5 . . ?
C12B C20B H20E 109.5 . . ?
H20D C20B H20E 109.5 . . ?
C12B C20B H20F 109.5 . . ?
H20D C20B H20F 109.5 . . ?
H20E C20B H20F 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
Pd1A C9A 1.937(4) . ?
Pd1A N2A 2.074(4) . ?
Pd1A N1A 2.078(3) . ?
Pd1A Br1A 2.5278(6) . ?
O1A C3A 1.335(5) . ?
O1A C2A 1.464(5) . ?
O2A C10A 1.325(5) . ?
O2A C11A 1.449(6) . ?
N1A C3A 1.291(5) . ?
N1A C1A 1.490(5) . ?
N2A C10A 1.293(6) . ?
N2A C12A 1.480(5) . ?
C1A C18A 1.509(6) . ?
C1A C17A 1.527(6) . ?
C1A C2A 1.533(6) . ?
C2A H2AA 0.9900 . ?
C2A H2AB 0.9900 . ?
C3A C4A 1.463(6) . ?
C4A C5A 1.379(6) . ?
C4A C9A 1.388(6) . ?
C5A C6A 1.399(6) . ?
C5A H5AA 0.9500 . ?
C6A C7A 1.413(6) . ?
C6A C13A 1.534(6) . ?
C7A C8A 1.385(6) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.381(6) . ?
C8A C10A 1.467(6) . ?
C11A C12A 1.557(7) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
C12A C20A 1.516(7) . ?
C12A C19A 1.520(7) . ?
C13A C14A 1.511(5) . ?
C13A C15A 1.534(5) . ?
C13A C16A 1.548(5) . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C16A H16A 0.9800 . ?
C16A H16B 0.9800 . ?
C16A H16C 0.9800 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
C18A H18A 0.9800 . ?
C18A H18B 0.9800 . ?
C18A H18C 0.9800 . ?
C19A H19A 0.9800 . ?
C19A H19B 0.9800 . ?
C19A H19C 0.9800 . ?
C20A H20A 0.9800 . ?
C20A H20B 0.9800 . ?
C20A H20C 0.9800 . ?
Pd1B C9B 1.923(4) . ?
Pd1B N1B 2.074(3) . ?
Pd1B N2B 2.079(3) . ?
Pd1B Br1B 2.5099(6) . ?
O1B C3B 1.340(5) . ?
O1B C2B 1.483(6) . ?
O2B C10B 1.335(5) . ?
O2B C11B 1.464(5) . ?
N1B C3B 1.291(5) . ?
N1B C1B 1.497(5) . ?
N2B C10B 1.287(5) . ?
N2B C12B 1.487(5) . ?
C1B C17B 1.516(6) . ?
C1B C18B 1.522(6) . ?
C1B C2B 1.531(6) . ?
C2B H2BA 0.9900 . ?
C2B H2BB 0.9900 . ?
C3B C4B 1.445(6) . ?
C4B C9B 1.391(6) . ?
C4B C5B 1.395(6) . ?
C5B C6B 1.397(6) . ?
C5B H5BA 0.9500 . ?
C6B C7B 1.406(6) . ?
C6B C13B 1.530(6) . ?
C7B C8B 1.373(6) . ?
C7B H7BA 0.9500 . ?
C8B C10B 1.423(6) . ?
C8B C9B 1.440(6) . ?
C11B C12B 1.530(6) . ?
C11B H11C 0.9900 . ?
C11B H11D 0.9900 . ?
C12B C20B 1.515(7) . ?
C12B C19B 1.530(6) . ?
C13B C14B 1.504(6) . ?
C13B C15B 1.524(6) . ?
C13B C16B 1.545(6) . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16B H16D 0.9800 . ?
C16B H16E 0.9800 . ?
C16B H16F 0.9800 . ?
C14' H14G 0.9800 . ?
C14' H14H 0.9800 . ?
C14' H14I 0.9800 . ?
C15' H15G 0.9800 . ?
C15' H15H 0.9800 . ?
C15' H15I 0.9800 . ?
C16' H16G 0.9800 . ?
C16' H16H 0.9800 . ?
C16' H16I 0.9800 . ?
C17B H17D 0.9800 . ?
C17B H17E 0.9800 . ?
C17B H17F 0.9800 . ?
C18B H18D 0.9800 . ?
C18B H18E 0.9800 . ?
C18B H18F 0.9800 . ?
C19B H19D 0.9800 . ?
C19B H19E 0.9800 . ?
C19B H19F 0.9800 . ?
C20B H20D 0.9800 . ?
C20B H20E 0.9800 . ?
C20B H20F 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
C9A Pd1A N1A C3A -5.0(3) . . . . ?
N2A Pd1A N1A C3A -1.5(5) . . . . ?
Br1A Pd1A N1A C3A 168.9(3) . . . . ?
C9A Pd1A N1A C1A -168.3(4) . . . . ?
N2A Pd1A N1A C1A -164.8(4) . . . . ?
Br1A Pd1A N1A C1A 5.6(4) . . . . ?
C9A Pd1A N2A C10A 1.9(3) . . . . ?
N1A Pd1A N2A C10A -1.5(5) . . . . ?
Br1A Pd1A N2A C10A -172.0(3) . . . . ?
C9A Pd1A N2A C12A 174.4(4) . . . . ?
N1A Pd1A N2A C12A 170.9(4) . . . . ?
Br1A Pd1A N2A C12A 0.5(4) . . . . ?
C3A N1A C1A C18A 130.9(4) . . . . ?
Pd1A N1A C1A C18A -65.2(5) . . . . ?
C3A N1A C1A C17A -105.5(4) . . . . ?
Pd1A N1A C1A C17A 58.3(5) . . . . ?
C3A N1A C1A C2A 12.0(4) . . . . ?
Pd1A N1A C1A C2A 175.8(3) . . . . ?
C3A O1A C2A C1A 13.4(4) . . . . ?
N1A C1A C2A O1A -15.1(4) . . . . ?
C18A C1A C2A O1A -134.2(4) . . . . ?
C17A C1A C2A O1A 99.4(4) . . . . ?
C1A N1A C3A O1A -4.3(5) . . . . ?
Pd1A N1A C3A O1A -172.5(3) . . . . ?
C1A N1A C3A C4A 172.4(3) . . . . ?
Pd1A N1A C3A C4A 4.1(4) . . . . ?
C2A O1A C3A N1A -6.2(5) . . . . ?
C2A O1A C3A C4A 177.4(4) . . . . ?
N1A C3A C4A C5A -174.1(4) . . . . ?
O1A C3A C4A C5A 2.4(7) . . . . ?
N1A C3A C4A C9A 0.0(5) . . . . ?
O1A C3A C4A C9A 176.5(3) . . . . ?
C9A C4A C5A C6A -1.0(6) . . . . ?
C3A C4A C5A C6A 172.5(4) . . . . ?
C4A C5A C6A C7A 1.3(6) . . . . ?
C4A C5A C6A C13A -175.1(4) . . . . ?
C5A C6A C7A C8A -0.9(6) . . . . ?
C13A C6A C7A C8A 175.7(4) . . . . ?
C6A C7A C8A C9A 0.2(6) . . . . ?
C6A C7A C8A C10A -172.2(4) . . . . ?
C7A C8A C9A C4A 0.1(6) . . . . ?
C10A C8A C9A C4A 174.0(4) . . . . ?
C7A C8A C9A Pd1A -169.6(3) . . . . ?
C10A C8A C9A Pd1A 4.3(5) . . . . ?
C5A C4A C9A C8A 0.3(6) . . . . ?
C3A C4A C9A C8A -174.4(4) . . . . ?
C5A C4A C9A Pd1A 170.1(3) . . . . ?
C3A C4A C9A Pd1A -4.7(4) . . . . ?
N2A Pd1A C9A C8A -3.6(3) . . . . ?
N1A Pd1A C9A C8A 175.1(3) . . . . ?
Br1A Pd1A C9A C8A 79.0(13) . . . . ?
N2A Pd1A C9A C4A -173.3(3) . . . . ?
N1A Pd1A C9A C4A 5.4(3) . . . . ?
Br1A Pd1A C9A C4A -90.7(12) . . . . ?
C12A N2A C10A O2A 4.2(5) . . . . ?
Pd1A N2A C10A O2A 178.8(3) . . . . ?
C12A N2A C10A C8A -174.8(4) . . . . ?
Pd1A N2A C10A C8A -0.2(5) . . . . ?
C11A O2A C10A N2A 0.4(5) . . . . ?
C11A O2A C10A C8A 179.3(4) . . . . ?
C9A C8A C10A N2A -2.5(5) . . . . ?
C7A C8A C10A N2A 170.6(4) . . . . ?
C9A C8A C10A O2A 178.6(4) . . . . ?
C7A C8A C10A O2A -8.3(7) . . . . ?
C10A O2A C11A C12A -4.4(5) . . . . ?
C10A N2A C12A C20A 111.4(4) . . . . ?
Pd1A N2A C12A C20A -61.3(5) . . . . ?
C10A N2A C12A C19A -126.1(5) . . . . ?
Pd1A N2A C12A C19A 61.2(6) . . . . ?
C10A N2A C12A C11A -6.3(5) . . . . ?
Pd1A N2A C12A C11A -179.0(3) . . . . ?
O2A C11A C12A N2A 6.3(5) . . . . ?
O2A C11A C12A C20A -109.6(4) . . . . ?
O2A C11A C12A C19A 124.1(4) . . . . ?
C5A C6A C13A C14A 111.9(5) . . . . ?
C7A C6A C13A C14A -64.4(5) . . . . ?
C5A C6A C13A C15A -124.5(5) . . . . ?
C7A C6A C13A C15A 59.2(5) . . . . ?
C5A C6A C13A C16A -7.1(5) . . . . ?
C7A C6A C13A C16A 176.6(4) . . . . ?
C9B Pd1B N1B C3B 2.9(3) . . . . ?
N2B Pd1B N1B C3B 0.0(5) . . . . ?
Br1B Pd1B N1B C3B -172.6(3) . . . . ?
C9B Pd1B N1B C1B 176.4(4) . . . . ?
N2B Pd1B N1B C1B 173.6(4) . . . . ?
Br1B Pd1B N1B C1B 1.0(4) . . . . ?
C9B Pd1B N2B C10B -1.4(3) . . . . ?
N1B Pd1B N2B C10B 1.5(5) . . . . ?
Br1B Pd1B N2B C10B 174.1(3) . . . . ?
C9B Pd1B N2B C12B -175.5(4) . . . . ?
N1B Pd1B N2B C12B -172.6(4) . . . . ?
Br1B Pd1B N2B C12B 0.0(4) . . . . ?
C3B N1B C1B C17B -130.0(4) . . . . ?
Pd1B N1B C1B C17B 56.3(5) . . . . ?
C3B N1B C1B C18B 106.4(4) . . . . ?
Pd1B N1B C1B C18B -67.3(5) . . . . ?
C3B N1B C1B C2B -12.2(4) . . . . ?
Pd1B N1B C1B C2B 174.1(3) . . . . ?
C3B O1B C2B C1B -15.5(5) . . . . ?
N1B C1B C2B O1B 16.3(4) . . . . ?
C17B C1B C2B O1B 133.9(4) . . . . ?
C18B C1B C2B O1B -100.2(4) . . . . ?
C1B N1B C3B O1B 2.9(5) . . . . ?
Pd1B N1B C3B O1B 178.4(3) . . . . ?
C1B N1B C3B C4B -176.9(3) . . . . ?
Pd1B N1B C3B C4B -1.5(5) . . . . ?
C2B O1B C3B N1B 8.3(5) . . . . ?
C2B O1B C3B C4B -171.9(4) . . . . ?
N1B C3B C4B C9B -1.5(5) . . . . ?
O1B C3B C4B C9B 178.6(4) . . . . ?
N1B C3B C4B C5B 175.3(4) . . . . ?
O1B C3B C4B C5B -4.5(7) . . . . ?
C9B C4B C5B C6B 0.1(6) . . . . ?
C3B C4B C5B C6B -176.5(4) . . . . ?
C4B C5B C6B C7B 0.1(6) . . . . ?
C4B C5B C6B C13B 176.4(4) . . . . ?
C5B C6B C7B C8B -0.9(6) . . . . ?
C13B C6B C7B C8B -177.3(4) . . . . ?
C6B C7B C8B C10B 172.6(4) . . . . ?
C6B C7B C8B C9B 1.4(6) . . . . ?
C5B C4B C9B C8B 0.4(6) . . . . ?
C3B C4B C9B C8B 177.7(3) . . . . ?
C5B C4B C9B Pd1B -173.1(3) . . . . ?
C3B C4B C9B Pd1B 4.2(4) . . . . ?
C7B C8B C9B C4B -1.2(5) . . . . ?
C10B C8B C9B C4B -174.6(3) . . . . ?
C7B C8B C9B Pd1B 172.3(3) . . . . ?
C10B C8B C9B Pd1B -1.1(4) . . . . ?
N1B Pd1B C9B C4B -4.0(3) . . . . ?
N2B Pd1B C9B C4B 174.9(3) . . . . ?
Br1B Pd1B C9B C4B 86.8(16) . . . . ?
N1B Pd1B C9B C8B -177.5(3) . . . . ?
N2B Pd1B C9B C8B 1.4(3) . . . . ?
Br1B Pd1B C9B C8B -86.7(15) . . . . ?
C12B N2B C10B O2B -0.9(5) . . . . ?
Pd1B N2B C10B O2B -176.7(3) . . . . ?
C12B N2B C10B C8B 177.1(4) . . . . ?
Pd1B N2B C10B C8B 1.2(5) . . . . ?
C11B O2B C10B N2B -2.4(5) . . . . ?
C11B O2B C10B C8B 179.7(4) . . . . ?
C7B C8B C10B N2B -172.0(4) . . . . ?
C9B C8B C10B N2B -0.2(5) . . . . ?
C7B C8B C10B O2B 5.8(7) . . . . ?
C9B C8B C10B O2B 177.6(3) . . . . ?
C10B O2B C11B C12B 4.4(5) . . . . ?
C10B N2B C12B C20B 122.9(4) . . . . ?
Pd1B N2B C12B C20B -62.8(5) . . . . ?
C10B N2B C12B C19B -114.3(4) . . . . ?
Pd1B N2B C12B C19B 60.0(5) . . . . ?
C10B N2B C12B C11B 3.5(5) . . . . ?
Pd1B N2B C12B C11B 177.8(3) . . . . ?
O2B C11B C12B N2B -4.7(4) . . . . ?
O2B C11B C12B C20B -122.0(4) . . . . ?
O2B C11B C12B C19B 110.8(4) . . . . ?
C5B C6B C13B C14B -111.8(6) . . . . ?
C7B C6B C13B C14B 64.4(6) . . . . ?
C5B C6B C13B C15B 124.0(6) . . . . ?
C7B C6B C13B C15B -59.8(6) . . . . ?
C5B C6B C13B C16B 7.3(7) . . . . ?
C7B C6B C13B C16B -176.6(5) . . . . ?
