#------------------------------------------------------------------------------
#$Date: 2020-01-31 01:45:05 +0200 (Fri, 31 Jan 2020) $
#$Revision: 247384 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/13/40/4134090.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_4134090
loop_
_publ_author_name
'Wang, Yaning'
'Chai, Junli'
'You, Chang'
'Zhang, Jie'
'Mi, Xueling'
'Zhang, Long'
'Luo, Sanzhong'
_publ_section_title
;
 π-Coordinating Chiral Primary Amine/Palladium Synergistic Catalysis for
 Asymmetric Allylic Alkylation.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b13026
_journal_year                    2020
_chemical_formula_moiety         '2(C21.05 H29 N2 Pd), 2(C F3 O3 S), C H2 Cl2'
_chemical_formula_sum            'C45.17 H60 Cl2 F6 N4 O6 Pd2 S2'
_chemical_formula_weight         1216.83
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
????
;
_cell_angle_alpha                106.417(14)
_cell_angle_beta                 110.789(12)
_cell_angle_gamma                93.976(15)
_cell_formula_units_Z            1
_cell_length_a                   9.365(3)
_cell_length_b                   11.859(3)
_cell_length_c                   13.177(3)
_cell_measurement_reflns_used    4833
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4826
_cell_measurement_theta_min      1.7508
_cell_volume                     1288.7(6)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0528
_diffrn_reflns_av_unetI/netI     0.0579
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15424
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.751
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.953
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.77968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_description       block
_exptl_crystal_F_000             619
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         1.326
_refine_diff_density_min         -0.906
_refine_diff_density_rms         0.129
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     378
_refine_ls_number_reflns         5875
_refine_ls_number_restraints     87
_refine_ls_restrained_S_all      1.199
_refine_ls_R_factor_all          0.0789
_refine_ls_R_factor_gt           0.0748
_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)+(0.0327P)²+9.3047P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1684
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5544
_reflns_number_total             5875
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja9b13026_si_002.cif
_cod_data_source_block           a
_cod_original_cell_volume        1288.6(6)
_cod_database_code               4134090
_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_max   0.878
_shelx_estimated_absorpt_t_min   0.862
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C16A-C15A = C18A-C15A = C17A-C15A
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C15A \\sim C16A \\sim C17A \\sim C18A:
within 1.7A with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C20) \\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(N2A)=Sof(H2AA)=Sof(H2AB)=Sof(C13A)=Sof(H13C)=Sof(H13D)=Sof(C14A)=
 Sof(H14A)=Sof(C16A)=Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17A)=Sof(H17D)=
 Sof(H17E)=Sof(H17F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(N2)=Sof(H2A)=Sof(H2B)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=Sof(H14)=
 Sof(C15)=Sof(C16)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 Sof(H17C)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=FVAR(1)
 Fixed Sof: C22(0.5) H22A(0.5) H22B(0.5)
5.a Riding coordinates:
 C20(H20)
5.b Ternary CH refined with riding coordinates:
 C14(H14), C14A(H14A)
5.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C12(H12A,H12B), C19(H19A,H19B), C21(H21A,H21B), N2(H2A,H2B),
 C13(H13A,H13B), N2A(H2AA,H2AB), C13A(H13C,H13D), C22(H22A,H22B)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C7(H7), C8(H8), C9(H9)
5.e Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16A(H16D,H16E,
 H16F), C17A(H17D,H17E,H17F), C18A(H18D,H18E,H18F)
;
_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 0.62143(6) 0.40627(4) 0.25701(4) 0.02840(15) Uani 1 1 d . . . . .
C1 C 0.7127(11) 0.1717(7) 0.1557(6) 0.058(2) Uani 1 1 d . . . . .
H1A H 0.720043 0.088793 0.155743 0.070 Uiso 1 1 calc R . . . .
H1B H 0.818622 0.221009 0.197822 0.070 Uiso 1 1 calc R . . . .
N1 N 0.6117(9) 0.2189(5) 0.2159(5) 0.0507(18) Uani 1 1 d . . . . .
C2 C 0.6519(9) 0.1719(6) 0.0339(6) 0.0386(16) Uani 1 1 d . . . . .
C3 C 0.7515(10) 0.1797(7) -0.0200(8) 0.055(2) Uani 1 1 d . . . . .
H3 H 0.860108 0.187183 0.020402 0.066 Uiso 1 1 calc R . . . .
C4 C 0.6925(13) 0.1767(8) -0.1356(9) 0.063(2) Uani 1 1 d . . . . .
H4 H 0.762223 0.182284 -0.172454 0.076 Uiso 1 1 calc R . . . .
C5 C 0.5418(12) 0.1663(7) -0.1932(7) 0.052(2) Uani 1 1 d . . . . .
H5 H 0.504616 0.163071 -0.271298 0.062 Uiso 1 1 calc R . . . .
C6 C 0.4344(9) 0.1597(6) -0.1404(6) 0.0408(17) Uani 1 1 d . . . . .
C7 C 0.2712(11) 0.1498(7) -0.1984(7) 0.059(3) Uani 1 1 d . . . . .
H7 H 0.229957 0.147481 -0.276246 0.070 Uiso 1 1 calc R . . . .
C8 C 0.1751(11) 0.1439(8) -0.1444(9) 0.068(3) Uani 1 1 d . . . . .
H8 H 0.066803 0.138616 -0.184307 0.082 Uiso 1 1 calc R . . . .
C9 C 0.2303(11) 0.1453(7) -0.0314(9) 0.063(3) Uani 1 1 d . . . . .
H9 H 0.159398 0.140908 0.004689 0.075 Uiso 1 1 calc R . . . .
C10 C 0.3855(9) 0.1528(6) 0.0290(6) 0.0409(16) Uani 1 1 d . . . . .
C11 C 0.4928(8) 0.1605(5) -0.0252(5) 0.0318(13) Uani 1 1 d . . . . .
C12 C 0.4486(13) 0.1506(7) 0.1499(7) 0.061(3) Uani 1 1 d . . . . .
H12A H 0.381594 0.185640 0.189264 0.073 Uiso 1 1 calc R . . . .
H12B H 0.445898 0.066563 0.148515 0.073 Uiso 1 1 calc R . . . .
C19 C 0.5405(15) 0.4410(8) 0.0997(7) 0.071(3) Uani 1 1 d . . . . .
H19A H 0.607226 0.428407 0.055218 0.085 Uiso 1 1 calc R . . . .
H19B H 0.427944 0.413774 0.051400 0.085 Uiso 1 1 calc R . . . .
C20 C 0.5801(18) 0.5398(10) 0.1842(10) 0.109(4) Uani 1 1 d . U . . .
H20 H 0.571866 0.602446 0.150814 0.130 Uiso 1 1 d R . . . .
C21 C 0.6266(17) 0.5872(9) 0.2867(9) 0.088(3) Uani 1 1 d . U . . .
H21A H 0.550223 0.621428 0.316490 0.106 Uiso 1 1 calc R . . . .
H21B H 0.730980 0.639210 0.324382 0.106 Uiso 1 1 calc R . . . .
N2 N 0.6728(19) 0.3982(17) 0.4237(19) 0.029(3) Uani 0.522(14) 1 d . . P A 1
H2A H 0.736602 0.466337 0.478383 0.035 Uiso 0.522(14) 1 calc R . P A 1
H2B H 0.584701 0.385438 0.436443 0.035 Uiso 0.522(14) 1 calc R . P A 1
C13 C 0.6224(18) 0.1935(11) 0.3277(10) 0.032(3) Uani 0.522(14) 1 d . . P A 1
H13A H 0.528290 0.208141 0.343463 0.038 Uiso 0.522(14) 1 calc R . P A 1
H13B H 0.633410 0.109609 0.321012 0.038 Uiso 0.522(14) 1 calc R . P A 1
C14 C 0.7640(16) 0.2787(11) 0.4209(10) 0.030(3) Uani 0.522(14) 1 d . . P A 1
H14 H 0.866327 0.281984 0.412958 0.037 Uiso 0.522(14) 1 calc R . P A 1
C15 C 0.748(3) 0.2578(17) 0.5412(17) 0.040(4) Uani 0.522(14) 1 d . U P A 1
C16 C 0.712(3) 0.1279(15) 0.5308(14) 0.063(5) Uani 0.522(14) 1 d . U P A 1
H16A H 0.741855 0.078098 0.471380 0.094 Uiso 0.522(14) 1 calc GR . P A 1
H16B H 0.599929 0.103986 0.509704 0.094 Uiso 0.522(14) 1 calc GR . P A 1
H16C H 0.769828 0.117283 0.604585 0.094 Uiso 0.522(14) 1 calc GR . P A 1
C17 C 0.924(3) 0.305(3) 0.5903(18) 0.056(6) Uani 0.522(14) 1 d . U P A 1
H17A H 0.971654 0.251492 0.546303 0.085 Uiso 0.522(14) 1 calc GR . P A 1
H17B H 0.969713 0.309745 0.671061 0.085 Uiso 0.522(14) 1 calc GR . P A 1
H17C H 0.942558 0.385522 0.585003 0.085 Uiso 0.522(14) 1 calc GR . P A 1
C18 C 0.681(3) 0.3309(18) 0.6242(18) 0.049(4) Uani 0.522(14) 1 d . U P A 1
H18A H 0.709016 0.416254 0.636484 0.074 Uiso 0.522(14) 1 calc GR . P A 1
H18B H 0.724469 0.316368 0.697888 0.074 Uiso 0.522(14) 1 calc GR . P A 1
H18C H 0.567713 0.306599 0.591333 0.074 Uiso 0.522(14) 1 calc GR . P A 1
N2A N 0.737(3) 0.400(2) 0.424(2) 0.050(6) Uani 0.478(14) 1 d . . P A 2
H2AA H 0.841423 0.407709 0.442451 0.059 Uiso 0.478(14) 1 calc R . P A 2
H2AB H 0.719564 0.459672 0.476592 0.059 Uiso 0.478(14) 1 calc R . P A 2
C13A C 0.7242(17) 0.2072(12) 0.3341(10) 0.027(3) Uani 0.478(14) 1 d . . P A 2
H13C H 0.720783 0.122052 0.328678 0.033 Uiso 0.478(14) 1 calc R . P A 2
H13D H 0.832728 0.244829 0.354396 0.033 Uiso 0.478(14) 1 calc R . P A 2
C14A C 0.6654(19) 0.2703(11) 0.4207(11) 0.029(3) Uani 0.478(14) 1 d . . P A 2
H14A H 0.553562 0.250060 0.408054 0.035 Uiso 0.478(14) 1 calc R . P A 2
C15A C 0.811(2) 0.2593(13) 0.5397(18) 0.039(5) Uani 0.52(3) 1 d D U . A 2
C16A C 0.838(3) 0.1306(13) 0.5281(14) 0.054(5) Uani 0.478(14) 1 d D U P A 2
H16D H 0.737511 0.075223 0.491050 0.081 Uiso 0.478(14) 1 calc GR . P A 2
H16E H 0.894218 0.125224 0.604508 0.081 Uiso 0.478(14) 1 calc GR . P A 2
H16F H 0.899354 0.109244 0.481197 0.081 Uiso 0.478(14) 1 calc GR . P A 2
C17A C 0.962(3) 0.348(2) 0.626(2) 0.051(6) Uani 0.478(14) 1 d D U P A 2
H17D H 1.039605 0.343924 0.591341 0.077 Uiso 0.478(14) 1 calc GR . P A 2
H17E H 1.002449 0.326026 0.695933 0.077 Uiso 0.478(14) 1 calc GR . P A 2
H17F H 0.941020 0.429066 0.645016 0.077 Uiso 0.478(14) 1 calc GR . P A 2
C18A C 0.685(2) 0.284(3) 0.5884(19) 0.054(5) Uani 0.478(14) 1 d D U P A 2
H18D H 0.669357 0.366335 0.596340 0.081 Uiso 0.478(14) 1 calc GR . P A 2
H18E H 0.718568 0.273162 0.663899 0.081 Uiso 0.478(14) 1 calc GR . P A 2
H18F H 0.587503 0.228166 0.536100 0.081 Uiso 0.478(14) 1 calc GR . P A 2
F1 F 0.7605(7) 0.8231(5) 0.5185(4) 0.0697(15) Uani 1 1 d . . . . .
S1 S 0.8095(2) 0.69214(16) 0.65451(16) 0.0400(4) Uani 1 1 d . . . . .
O1 O 0.6493(7) 0.6374(5) 0.5939(6) 0.0667(18) Uani 1 1 d . . . . .
F2 F 0.7309(7) 0.9031(4) 0.6743(5) 0.0698(15) Uani 1 1 d . . . . .
O2 O 0.9121(7) 0.6372(5) 0.6057(5) 0.0549(14) Uani 1 1 d . . . . .
F3 F 0.9586(6) 0.8980(4) 0.6752(5) 0.0686(15) Uani 1 1 d . . . . .
O3 O 0.8662(8) 0.7273(6) 0.7768(5) 0.0681(18) Uani 1 1 d . . . . .
C0AA C 0.8157(9) 0.8361(7) 0.6306(7) 0.0437(17) Uani 1 1 d . . . . .
Cl1 Cl 0.0796(6) 0.4181(4) -0.0518(5) 0.1529(19) Uani 1 1 d . . . . .
C22 C -0.014(4) 0.528(2) -0.073(2) 0.123(12) Uani 0.5 1 d . . P . .
H22A H -0.105723 0.498556 -0.147184 0.148 Uiso 0.5 1 calc R . P . .
H22B H 0.054695 0.594009 -0.074307 0.148 Uiso 0.5 1 calc R . 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'
Cl Cl 0.1484 0.1585 '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'
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'
S S 0.1246 0.1234 '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
C19 Pd1 N1 106.7(3) . .
C20 Pd1 N1 142.7(4) . .
C20 Pd1 C19 35.9(4) . .
C20 Pd1 C21 33.9(4) . .
C20 Pd1 N2 134.4(6) . .
C20 Pd1 N2A 135.6(8) . .
C21 Pd1 N1 176.6(3) . .
C21 Pd1 C19 69.8(4) . .
C21 Pd1 N2 100.9(6) . .
C21 Pd1 N2A 102.3(8) . .
N2 Pd1 N1 82.5(5) . .
N2 Pd1 C19 167.7(5) . .
N2A Pd1 N1 81.1(7) . .
N2A Pd1 C19 168.9(7) . .
H1A C1 H1B 107.9 . .
N1 C1 H1A 109.2 . .
N1 C1 H1B 109.2 . .
N1 C1 C2 112.1(6) . .
C2 C1 H1A 109.2 . .
C2 C1 H1B 109.2 . .
C1 N1 Pd1 114.5(5) . .
C1 N1 C12 110.2(6) . .
C1 N1 C13 120.9(7) . .
C1 N1 C13A 93.0(7) . .
C12 N1 Pd1 111.8(5) . .
C12 N1 C13 93.0(8) . .
C12 N1 C13A 123.5(8) . .
C13 N1 Pd1 104.4(6) . .
C13A N1 Pd1 102.7(6) . .
C3 C2 C1 120.5(8) . .
C3 C2 C11 120.1(7) . .
C11 C2 C1 119.4(7) . .
C2 C3 H3 120.0 . .
C2 C3 C4 120.0(8) . .
C4 C3 H3 120.0 . .
C3 C4 H4 119.6 . .
C5 C4 C3 120.9(8) . .
C5 C4 H4 119.6 . .
C4 C5 H5 119.4 . .
C4 C5 C6 121.1(7) . .
C6 C5 H5 119.4 . .
C5 C6 C7 123.2(7) . .
C11 C6 C5 118.1(7) . .
C11 C6 C7 118.6(8) . .
C6 C7 H7 119.6 . .
C8 C7 C6 120.7(8) . .
C8 C7 H7 119.6 . .
C7 C8 H8 119.3 . .
C7 C8 C9 121.4(8) . .
C9 C8 H8 119.3 . .
C8 C9 H9 119.5 . .
C10 C9 C8 121.0(9) . .
C10 C9 H9 119.5 . .
C9 C10 C11 119.5(7) . .
C9 C10 C12 122.4(8) . .
C11 C10 C12 118.1(7) . .
C2 C11 C6 119.8(7) . .
C2 C11 C10 121.4(6) . .
C6 C11 C10 118.8(7) . .
N1 C12 C10 111.8(6) . .
N1 C12 H12A 109.3 . .
N1 C12 H12B 109.3 . .
C10 C12 H12A 109.3 . .
C10 C12 H12B 109.3 . .
H12A C12 H12B 107.9 . .
Pd1 C19 H19A 116.6 . .
Pd1 C19 H19B 116.6 . .
H19A C19 H19B 113.6 . .
C20 C19 Pd1 70.0(5) . .
C20 C19 H19A 116.6 . .
C20 C19 H19B 116.6 . .
Pd1 C20 H20 174.0 . .
C19 C20 Pd1 74.0(6) . .
C19 C20 H20 105.9 . .
C21 C20 Pd1 73.1(6) . .
C21 C20 C19 147.1(10) . .
C21 C20 H20 107.0 . .
Pd1 C21 H21A 116.2 . .
Pd1 C21 H21B 116.2 . .
C20 C21 Pd1 73.0(7) . .
C20 C21 H21A 116.2 . .
C20 C21 H21B 116.2 . .
H21A C21 H21B 113.2 . .
Pd1 N2 H2A 111.4 . .
Pd1 N2 H2B 111.4 . .
H2A N2 H2B 109.3 . .
C14 N2 Pd1 101.9(10) . .
C14 N2 H2A 111.4 . .
C14 N2 H2B 111.4 . .
N1 C13 H13A 110.7 . .
N1 C13 H13B 110.7 . .
H13A C13 H13B 108.8 . .
C14 C13 N1 105.1(10) . .
C14 C13 H13A 110.7 . .
C14 C13 H13B 110.7 . .
N2 C14 H14 120.4 . .
N2 C14 C15 96.1(12) . .
C13 C14 N2 92.8(11) . .
C13 C14 H14 120.4 . .
C13 C14 C15 100.7(13) . .
C15 C14 H14 120.4 . .
C16 C15 C14 113.9(14) . .
C16 C15 C17 111.9(19) . .
C16 C15 C18 107.8(16) . .
C17 C15 C14 80.7(15) . .
C18 C15 C14 130.1(16) . .
C18 C15 C17 108.1(19) . .
C15 C16 H16A 109.5 . .
C15 C16 H16B 109.5 . .
C15 C16 H16C 109.5 . .
H16A C16 H16B 109.5 . .
H16A C16 H16C 109.5 . .
H16B C16 H16C 109.5 . .
C15 C17 H17A 109.5 . .
C15 C17 H17B 109.5 . .
C15 C17 H17C 109.5 . .
H17A C17 H17B 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
C15 C18 H18A 109.5 . .
C15 C18 H18B 109.5 . .
C15 C18 H18C 109.5 . .
H18A C18 H18B 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
Pd1 N2A H2AA 110.7 . .
Pd1 N2A H2AB 110.7 . .
H2AA N2A H2AB 108.8 . .
C14A N2A Pd1 105.3(14) . .
C14A N2A H2AA 110.7 . .
C14A N2A H2AB 110.7 . .
N1 C13A H13C 110.6 . .
N1 C13A H13D 110.6 . .
H13C C13A H13D 108.8 . .
C14A C13A N1 105.5(10) . .
C14A C13A H13C 110.6 . .
C14A C13A H13D 110.6 . .
N2A C14A H14A 120.7 . .
N2A C14A C15A 99.0(13) . .
C13A C14A N2A 92.0(14) . .
C13A C14A H14A 120.7 . .
C13A C14A C15A 97.5(12) . .
C15A C14A H14A 120.7 . .
C16A C15A C14A 113.5(13) . .
C16A C15A C17A 108.9(16) . .
C17A C15A C14A 130.7(15) . .
C18A C15A C14A 80.6(13) . .
C18A C15A C16A 110.0(19) . .
C18A C15A C17A 107(2) . .
C15A C16A H16D 109.5 . .
C15A C16A H16E 109.5 . .
C15A C16A H16F 109.5 . .
H16D C16A H16E 109.5 . .
H16D C16A H16F 109.5 . .
H16E C16A H16F 109.5 . .
C15A C17A H17D 109.5 . .
C15A C17A H17E 109.5 . .
C15A C17A H17F 109.5 . .
H17D C17A H17E 109.5 . .
H17D C17A H17F 109.5 . .
H17E C17A H17F 109.5 . .
C15A C18A H18D 109.5 . .
C15A C18A H18E 109.5 . .
C15A C18A H18F 109.5 . .
H18D C18A H18E 109.5 . .
H18D C18A H18F 109.5 . .
H18E C18A H18F 109.5 . .
O1 S1 O2 115.0(4) . .
O1 S1 O3 115.9(4) . .
O1 S1 C0AA 103.1(4) . .
O2 S1 C0AA 103.1(4) . .
O3 S1 O2 114.8(4) . .
O3 S1 C0AA 102.1(4) . .
F1 C0AA S1 111.8(5) . .
F2 C0AA F1 106.3(7) . .
F2 C0AA S1 112.2(5) . .
F3 C0AA F1 106.2(7) . .
F3 C0AA S1 112.1(6) . .
F3 C0AA F2 107.8(6) . .
C22 Cl1 C22 73.4(14) . 2_565
Cl1 C22 Cl1 106.6(14) . 2_565
Cl1 C22 H22A 110.4 . .
Cl1 C22 H22A 110.4 2_565 .
Cl1 C22 H22B 110.4 . .
Cl1 C22 H22B 110.4 2_565 .
H22A C22 H22B 108.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pd1 N1 2.120(6) .
Pd1 C19 2.110(8) .
Pd1 C20 2.063(9) .
Pd1 C21 2.064(10) .
Pd1 N2 2.11(2) .
Pd1 N2A 2.11(2) .
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C1 N1 1.480(11) .
C1 C2 1.501(9) .
N1 C12 1.495(12) .
N1 C13 1.556(12) .
N1 C13A 1.591(13) .
C2 C3 1.370(11) .
C2 C11 1.391(10) .
C3 H3 0.9500 .
C3 C4 1.414(13) .
C4 H4 0.9500 .
C4 C5 1.321(13) .
C5 H5 0.9500 .
C5 C6 1.420(11) .
C6 C7 1.425(11) .
C6 C11 1.416(9) .
C7 H7 0.9500 .
C7 C8 1.340(14) .
C8 H8 0.9500 .
C8 C9 1.387(14) .
C9 H9 0.9500 .
C9 C10 1.369(12) .
C10 C11 1.436(10) .
C10 C12 1.498(11) .
C12 H12A 0.9900 .
C12 H12B 0.9900 .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C19 C20 1.288(14) .
C20 H20 0.9598 .
C20 C21 1.204(14) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
N2 H2A 0.9100 .
N2 H2B 0.9100 .
N2 C14 1.70(2) .
C13 H13A 0.9900 .
C13 H13B 0.9900 .
C13 C14 1.498(19) .
C14 H14 1.0000 .
C14 C15 1.73(2) .
C15 C16 1.51(2) .
C15 C17 1.54(3) .
C15 C18 1.54(2) .
C16 H16A 0.9800 .
C16 H16B 0.9800 .
C16 H16C 0.9800 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
N2A H2AA 0.9100 .
N2A H2AB 0.9100 .
N2A C14A 1.62(3) .
C13A H13C 0.9900 .
C13A H13D 0.9900 .
C13A C14A 1.48(2) .
C14A H14A 1.0000 .
C14A C15A 1.72(2) .
C15A C16A 1.539(10) .
C15A C17A 1.542(10) .
C15A C18A 1.535(10) .
C16A H16D 0.9800 .
C16A H16E 0.9800 .
C16A H16F 0.9800 .
C17A H17D 0.9800 .
C17A H17E 0.9800 .
C17A H17F 0.9800 .
C18A H18D 0.9800 .
C18A H18E 0.9800 .
C18A H18F 0.9800 .
F1 C0AA 1.338(9) .
S1 O1 1.425(6) .
S1 O2 1.432(5) .
S1 O3 1.427(6) .
S1 C0AA 1.822(8) .
F2 C0AA 1.321(8) .
F3 C0AA 1.318(8) .
Cl1 C22 1.91(3) 2_565
Cl1 C22 1.65(3) .
C22 H22A 0.9900 .
C22 H22B 0.9900 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A S1 0.91 2.85 3.70(2) 155.1 . yes
N2 H2A O1 0.91 2.54 3.16(2) 125.3 . yes
N2 H2A O2 0.91 2.30 3.20(2) 174.3 . yes
N2 H2B O1 0.91 2.07 2.934(17) 158.8 2_666 yes
N2A H2AA O2 0.91 2.65 3.49(2) 152.8 2_766 yes
N2A H2AB S1 0.91 2.90 3.74(3) 152.7 . yes
N2A H2AB O1 0.91 2.52 3.42(3) 170.2 . yes
N2A H2AB O2 0.91 2.42 3.02(3) 123.4 . yes
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_4
Pd1 N1 C12 C10 72.3(7) . .
Pd1 N1 C13 C14 -52.6(10) . .
Pd1 N1 C13A C14A 54.0(11) . .
Pd1 C19 C20 C21 -3(3) . .
Pd1 N2 C14 C13 -62.8(10) . .
Pd1 N2 C14 C15 -163.9(10) . .
Pd1 N2A C14A C13A 62.6(14) . .
Pd1 N2A C14A C15A 160.6(11) . .
C1 N1 C12 C10 -56.3(8) . .
C1 N1 C13 C14 78.2(11) . .
C1 N1 C13A C14A 170.0(10) . .
C1 C2 C3 C4 178.3(7) . .
C1 C2 C11 C6 -179.5(6) . .
C1 C2 C11 C10 2.3(9) . .
N1 C1 C2 C3 153.1(7) . .
N1 C1 C2 C11 -28.8(9) . .
N1 C13 C14 N2 75.0(12) . .
N1 C13 C14 C15 171.8(10) . .
N1 C13A C14A N2A -75.3(14) . .
N1 C13A C14A C15A -174.6(9) . .
C2 C1 N1 Pd1 -71.8(7) . .
C2 C1 N1 C12 55.4(8) . .
C2 C1 N1 C13 161.9(8) . .
C2 C1 N1 C13A -177.1(8) . .
C2 C3 C4 C5 -0.1(13) . .
C3 C2 C11 C6 -1.4(10) . .
C3 C2 C11 C10 -179.6(7) . .
C3 C4 C5 C6 1.0(13) . .
C4 C5 C6 C7 179.2(8) . .
C4 C5 C6 C11 -2.1(11) . .
C5 C6 C7 C8 180.0(8) . .
C5 C6 C11 C2 2.3(9) . .
C5 C6 C11 C10 -179.4(6) . .
C6 C7 C8 C9 -1.0(13) . .
C7 C6 C11 C2 -179.0(6) . .
C7 C6 C11 C10 -0.7(9) . .
C7 C8 C9 C10 0.0(13) . .
C8 C9 C10 C11 0.6(11) . .
C8 C9 C10 C12 -178.0(7) . .
C9 C10 C11 C2 178.1(7) . .
C9 C10 C11 C6 -0.2(10) . .
C9 C10 C12 N1 -151.0(7) . .
C11 C2 C3 C4 0.3(11) . .
C11 C6 C7 C8 1.3(11) . .
C11 C10 C12 N1 30.4(9) . .
C12 N1 C13 C14 -166.0(10) . .
C12 N1 C13A C14A -73.3(12) . .
C12 C10 C11 C2 -3.3(9) . .
C12 C10 C11 C6 178.4(6) . .
C19 C20 C21 Pd1 3(3) . .
N2 C14 C15 C16 140.8(18) . .
N2 C14 C15 C17 -109.3(15) . .
N2 C14 C15 C18 -3(3) . .
C13 N1 C12 C10 179.2(8) . .
C13 C14 C15 C16 47(2) . .
C13 C14 C15 C17 156.7(14) . .
C13 C14 C15 C18 -97(2) . .
N2A C14A C15A C16A -145.8(17) . .
N2A C14A C15A C17A 1(3) . .
N2A C14A C15A C18A 106.4(18) . .
C13A N1 C12 C10 -164.4(8) . .
C13A C14A C15A C16A -52.6(18) . .
C13A C14A C15A C17A 95(2) . .
C13A C14A C15A C18A -160.4(15) . .
O1 S1 C0AA F1 -57.0(6) . .
O1 S1 C0AA F2 62.3(7) . .
O1 S1 C0AA F3 -176.1(6) . .
O2 S1 C0AA F1 63.0(6) . .
O2 S1 C0AA F2 -177.7(6) . .
O2 S1 C0AA F3 -56.1(6) . .
O3 S1 C0AA F1 -177.7(6) . .
O3 S1 C0AA F2 -58.3(7) . .
O3 S1 C0AA F3 63.2(6) . .
C22 Cl1 C22 Cl1 0.000(4) 2_565 2_565
