#------------------------------------------------------------------------------
#$Date: 2016-03-23 16:13:23 +0200 (Wed, 23 Mar 2016) $
#$Revision: 179367 $
#$URL: svn://www.crystallography.net/cod/cif/4/32/64/4326441.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_4326441
loop_
_publ_author_name
'Graeme Nawn'
'Kate M. Waldie'
'Simon R. Oakley'
'Brendan D. Peters'
'Derek Mandel'
'Brian O. Patrick'
'Robert McDonald'
'Robin G. Hicks'
_publ_section_title
;
 Redox-Active Bridging Ligands Based on Indigo Diimine ("Nindigo")
 Derivatives
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9826
_journal_page_last               9837
_journal_paper_doi               10.1021/ic200388y
_journal_volume                  50
_journal_year                    2011
_chemical_formula_sum            'C40 H24 F12 N4 O6 Pd2'
_chemical_formula_weight         1097.43
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.128(4)
_cell_angle_beta                 96.593(4)
_cell_angle_gamma                102.633(4)
_cell_formula_units_Z            1
_cell_length_a                   5.5243(4)
_cell_length_b                   11.0622(8)
_cell_length_c                   16.4452(12)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.79
_cell_measurement_theta_min      2.45
_cell_volume                     962.56(12)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       'area detector'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            28767
_diffrn_reflns_theta_full        27.92
_diffrn_reflns_theta_max         27.92
_diffrn_reflns_theta_min         1.91
_exptl_absorpt_coefficient_mu    1.048
_exptl_absorpt_correction_T_max  0.979
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.893
_exptl_crystal_description       needle
_exptl_crystal_F_000             540
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.074
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         4506
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.028
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0269P)²+2.2959P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0779
_refine_ls_wR_factor_ref         0.0905
_reflns_number_gt                3603
_reflns_number_total             4506
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic200388y_si_007.cif
_cod_data_source_block           rh034
_cod_database_code               4326441
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6066(6) 0.5335(3) 0.4877(2) 0.0221(7) Uani 1 1 d . . .
C2 C 0.7753(6) 0.6456(3) 0.5358(2) 0.0222(7) Uani 1 1 d . . .
C3 C 0.9647(6) 0.6857(3) 0.4840(2) 0.0236(7) Uani 1 1 d . . .
C4 C 1.1832(7) 0.7819(3) 0.4956(2) 0.0281(8) Uani 1 1 d . . .
H4 H 1.2203 0.8448 0.5431 0.034 Uiso 1 1 calc R . .
C5 C 1.3444(7) 0.7842(4) 0.4371(2) 0.0308(8) Uani 1 1 d . . .
H5 H 1.4918 0.8497 0.4439 0.037 Uiso 1 1 calc R . .
C6 C 1.2914(7) 0.6908(4) 0.3681(2) 0.0293(8) Uani 1 1 d . . .
H6 H 1.4050 0.6933 0.3288 0.035 Uiso 1 1 calc R . .
C7 C 1.0785(7) 0.5951(3) 0.3555(2) 0.0271(8) Uani 1 1 d . . .
H7 H 1.0472 0.5310 0.3088 0.032 Uiso 1 1 calc R . .
C8 C 0.9087(6) 0.5938(3) 0.4125(2) 0.0226(7) Uani 1 1 d . . .
C9 C 0.8219(9) 0.5443(4) 0.1183(3) 0.0441(11) Uani 1 1 d . . .
C10 C 0.6355(7) 0.4563(4) 0.1589(2) 0.0326(9) Uani 1 1 d . . .
C11 C 0.4733(8) 0.3547(4) 0.1099(2) 0.0400(10) Uani 1 1 d . . .
H11 H 0.4824 0.3404 0.0522 0.048 Uiso 1 1 calc R . .
C12 C 0.2980(8) 0.2729(4) 0.1422(2) 0.0364(9) Uani 1 1 d . A .
C13 C 0.1164(11) 0.1661(5) 0.0818(3) 0.0547(13) Uani 1 1 d . . .
C14 C 0.0755(7) 0.1911(3) 0.3514(2) 0.0248(7) Uani 1 1 d . . .
C15 C 0.1318(7) 0.0788(3) 0.3654(2) 0.0316(8) Uani 1 1 d . . .
H15 H 0.2811 0.0786 0.4003 0.038 Uiso 1 1 calc R . .
C16 C -0.0303(8) -0.0331(4) 0.3281(3) 0.0360(9) Uani 1 1 d . . .
H16 H 0.0066 -0.1103 0.3382 0.043 Uiso 1 1 calc R . .
C17 C -0.2451(7) -0.0332(3) 0.2766(2) 0.0330(9) Uani 1 1 d . . .
C18 C -0.3049(7) 0.0790(4) 0.2635(2) 0.0332(9) Uani 1 1 d . . .
H18 H -0.4560 0.0793 0.2297 0.040 Uiso 1 1 calc R . .
C19 C -0.1402(7) 0.1905(3) 0.3008(2) 0.0296(8) Uani 1 1 d . . .
H19 H -0.1773 0.2679 0.2911 0.035 Uiso 1 1 calc R . .
C20 C -0.5865(10) -0.1514(5) 0.1768(4) 0.0655(15) Uani 1 1 d . . .
H20A H -0.7124 -0.1133 0.2003 0.098 Uiso 1 1 calc R . .
H20B H -0.6636 -0.2386 0.1521 0.098 Uiso 1 1 calc R . .
H20C H -0.5210 -0.1045 0.1341 0.098 Uiso 1 1 calc R . .
N1 N 0.6870(5) 0.5052(3) 0.41342(17) 0.0221(6) Uani 1 1 d . . .
N2 N 0.2449(5) 0.3089(3) 0.38845(17) 0.0238(6) Uani 1 1 d . . .
O1 O 0.6578(5) 0.4901(2) 0.23582(15) 0.0321(6) Uani 1 1 d . . .
O2 O 0.2591(5) 0.2731(2) 0.21584(15) 0.0371(6) Uani 1 1 d . . .
O3 O -0.3882(6) -0.1480(3) 0.2400(2) 0.0487(8) Uani 1 1 d . . .
F1 F 0.8155(7) 0.6609(3) 0.1379(2) 0.0849(11) Uani 1 1 d . . .
F2 F 1.0549(5) 0.5349(3) 0.14231(18) 0.0614(8) Uani 1 1 d . . .
F3 F 0.7847(6) 0.5172(3) 0.03624(16) 0.0770(10) Uani 1 1 d . . .
F4 F 0.190(3) 0.1431(19) 0.0114(9) 0.128(6) Uani 0.70(4) 1 d P A 1
F5 F 0.079(3) 0.0605(13) 0.1117(7) 0.084(4) Uani 0.70(4) 1 d P A 1
F6 F -0.098(3) 0.1906(17) 0.0694(14) 0.123(7) Uani 0.70(4) 1 d P A 1
Pd1 Pd 0.46818(5) 0.39445(3) 0.315707(16) 0.02434(10) Uani 1 1 d . A .
F4B F 0.122(12) 0.180(4) 0.0070(15) 0.155(19) Uani 0.30(4) 1 d P A 2
F5B F 0.165(13) 0.065(3) 0.093(4) 0.144(18) Uani 0.30(4) 1 d P A 2
F6B F -0.119(6) 0.158(5) 0.090(2) 0.118(16) Uani 0.30(4) 1 d P A 2
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'
F F 0.0171 0.0103 '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
N1 C1 C1 124.8(4) . 2_666
N1 C1 C2 110.2(3) . .
C1 C1 C2 125.0(4) 2_666 .
N2 C2 C3 130.4(3) 2_666 .
N2 C2 C1 124.1(3) 2_666 .
C3 C2 C1 105.4(3) . .
C4 C3 C8 120.1(3) . .
C4 C3 C2 133.8(3) . .
C8 C3 C2 105.8(3) . .
C5 C4 C3 119.1(3) . .
C5 C4 H4 120.4 . .
C3 C4 H4 120.4 . .
C4 C5 C6 120.3(3) . .
C4 C5 H5 119.8 . .
C6 C5 H5 119.8 . .
C7 C6 C5 121.6(3) . .
C7 C6 H6 119.2 . .
C5 C6 H6 119.2 . .
C6 C7 C8 118.9(3) . .
C6 C7 H7 120.6 . .
C8 C7 H7 120.6 . .
N1 C8 C7 128.7(3) . .
N1 C8 C3 111.3(3) . .
C7 C8 C3 119.9(3) . .
F1 C9 F3 107.9(4) . .
F1 C9 F2 107.5(4) . .
F3 C9 F2 105.8(4) . .
F1 C9 C10 112.1(4) . .
F3 C9 C10 112.9(4) . .
F2 C9 C10 110.3(4) . .
O1 C10 C11 129.2(4) . .
O1 C10 C9 112.2(3) . .
C11 C10 C9 118.6(3) . .
C10 C11 C12 121.6(4) . .
C10 C11 H11 119.2 . .
C12 C11 H11 119.2 . .
O2 C12 C11 129.3(4) . .
O2 C12 C13 113.0(4) . .
C11 C12 C13 117.7(4) . .
F5B C13 F4B 110(2) . .
F5B C13 F6 128(3) . .
F4B C13 F6 84(3) . .
F5B C13 F4 84(3) . .
F4B C13 F4 28(3) . .
F6 C13 F4 108.6(11) . .
F5B C13 F5 27(4) . .
F4B C13 F5 127(2) . .
F6 C13 F5 105.7(11) . .
F4 C13 F5 106.0(11) . .
F5B C13 F6B 108(3) . .
F4B C13 F6B 103(3) . .
F6 C13 F6B 24(2) . .
F4 C13 F6B 122.9(13) . .
F5 C13 F6B 83(2) . .
F5B C13 C12 109.5(17) . .
F4B C13 C12 112.9(16) . .
F6 C13 C12 110.1(8) . .
F4 C13 C12 114.1(7) . .
F5 C13 C12 111.9(7) . .
F6B C13 C12 113.6(13) . .
C19 C14 C15 119.8(3) . .
C19 C14 N2 119.7(3) . .
C15 C14 N2 120.5(3) . .
C16 C15 C14 119.6(4) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
C17 C16 C15 120.4(4) . .
C17 C16 H16 119.8 . .
C15 C16 H16 119.8 . .
O3 C17 C16 116.1(4) . .
O3 C17 C18 123.6(4) . .
C16 C17 C18 120.3(3) . .
C19 C18 C17 118.8(4) . .
C19 C18 H18 120.6 . .
C17 C18 H18 120.6 . .
C14 C19 C18 121.0(3) . .
C14 C19 H19 119.5 . .
C18 C19 H19 119.5 . .
O3 C20 H20A 109.5 . .
O3 C20 H20B 109.5 . .
H20A C20 H20B 109.5 . .
O3 C20 H20C 109.5 . .
H20A C20 H20C 109.5 . .
H20B C20 H20C 109.5 . .
C1 N1 C8 107.2(3) . .
C1 N1 Pd1 123.6(2) . .
C8 N1 Pd1 126.6(2) . .
C2 N2 C14 117.5(3) 2_666 .
C2 N2 Pd1 125.9(2) 2_666 .
C14 N2 Pd1 116.4(2) . .
C10 O1 Pd1 125.8(2) . .
C12 O2 Pd1 125.4(3) . .
C17 O3 C20 117.5(4) . .
N2 Pd1 N1 91.14(11) . .
N2 Pd1 O1 172.63(11) . .
N1 Pd1 O1 91.87(11) . .
N2 Pd1 O2 89.12(11) . .
N1 Pd1 O2 176.24(12) . .
O1 Pd1 O2 88.31(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.370(4) .
C1 C1 1.379(7) 2_666
C1 C2 1.454(5) .
C2 N2 1.311(4) 2_666
C2 C3 1.454(5) .
C3 C4 1.400(5) .
C3 C8 1.411(5) .
C4 C5 1.383(5) .
C4 H4 0.9500 .
C5 C6 1.393(5) .
C5 H5 0.9500 .
C6 C7 1.375(5) .
C6 H6 0.9500 .
C7 C8 1.400(5) .
C7 H7 0.9500 .
C8 N1 1.394(4) .
C9 F1 1.300(5) .
C9 F3 1.327(5) .
C9 F2 1.332(5) .
C9 C10 1.527(6) .
C10 O1 1.258(4) .
C10 C11 1.373(6) .
C11 C12 1.376(6) .
C11 H11 0.9500 .
C12 O2 1.254(5) .
C12 C13 1.533(6) .
C13 F5B 1.24(3) .
C13 F4B 1.26(2) .
C13 F6 1.272(14) .
C13 F4 1.285(10) .
C13 F5 1.307(13) .
C13 F6B 1.30(3) .
C14 C19 1.372(5) .
C14 C15 1.384(5) .
C14 N2 1.444(4) .
C15 C16 1.381(5) .
C15 H15 0.9500 .
C16 C17 1.376(6) .
C16 H16 0.9500 .
C17 O3 1.365(4) .
C17 C18 1.387(6) .
C18 C19 1.385(5) .
C18 H18 0.9500 .
C19 H19 0.9500 .
C20 O3 1.412(6) .
C20 H20A 0.9800 .
C20 H20B 0.9800 .
C20 H20C 0.9800 .
N1 Pd1 1.990(3) .
N2 C2 1.311(4) 2_666
N2 Pd1 1.989(3) .
O1 Pd1 2.029(2) .
O2 Pd1 2.043(3) .
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
N1 C1 C2 N2 -175.7(3) . 2_666
C1 C1 C2 N2 5.5(6) 2_666 2_666
N1 C1 C2 C3 1.1(4) . .
C1 C1 C2 C3 -177.7(4) 2_666 .
N2 C2 C3 C4 0.3(7) 2_666 .
C1 C2 C3 C4 -176.2(4) . .
N2 C2 C3 C8 173.1(3) 2_666 .
C1 C2 C3 C8 -3.5(4) . .
C8 C3 C4 C5 -1.1(5) . .
C2 C3 C4 C5 170.8(4) . .
C3 C4 C5 C6 -1.0(5) . .
C4 C5 C6 C7 0.7(5) . .
C5 C6 C7 C8 1.6(5) . .
C6 C7 C8 N1 -178.0(3) . .
C6 C7 C8 C3 -3.6(5) . .
C4 C3 C8 N1 178.7(3) . .
C2 C3 C8 N1 4.7(4) . .
C4 C3 C8 C7 3.4(5) . .
C2 C3 C8 C7 -170.6(3) . .
F1 C9 C10 O1 -51.7(5) . .
F3 C9 C10 O1 -173.8(4) . .
F2 C9 C10 O1 68.1(5) . .
F1 C9 C10 C11 128.8(4) . .
F3 C9 C10 C11 6.7(6) . .
F2 C9 C10 C11 -111.4(4) . .
O1 C10 C11 C12 1.7(7) . .
C9 C10 C11 C12 -178.9(4) . .
C10 C11 C12 O2 -1.8(8) . .
C10 C11 C12 C13 176.9(4) . .
O2 C12 C13 F5B -71(5) . .
C11 C12 C13 F5B 111(4) . .
O2 C12 C13 F4B 167(4) . .
C11 C12 C13 F4B -12(4) . .
O2 C12 C13 F6 75.1(15) . .
C11 C12 C13 F6 -103.8(15) . .
O2 C12 C13 F4 -162.6(15) . .
C11 C12 C13 F4 18.5(16) . .
O2 C12 C13 F5 -42.1(10) . .
C11 C12 C13 F5 139.0(9) . .
O2 C12 C13 F6B 50(3) . .
C11 C12 C13 F6B -129(3) . .
C19 C14 C15 C16 -0.1(6) . .
N2 C14 C15 C16 -178.8(3) . .
C14 C15 C16 C17 0.9(6) . .
C15 C16 C17 O3 177.4(4) . .
C15 C16 C17 C18 -2.0(6) . .
O3 C17 C18 C19 -177.0(4) . .
C16 C17 C18 C19 2.4(6) . .
C15 C14 C19 C18 0.5(6) . .
N2 C14 C19 C18 179.2(3) . .
C17 C18 C19 C14 -1.6(6) . .
C1 C1 N1 C8 -179.5(4) 2_666 .
C2 C1 N1 C8 1.7(4) . .
C1 C1 N1 Pd1 18.0(6) 2_666 .
C2 C1 N1 Pd1 -160.9(2) . .
C7 C8 N1 C1 170.7(3) . .
C3 C8 N1 C1 -4.1(4) . .
C7 C8 N1 Pd1 -27.4(5) . .
C3 C8 N1 Pd1 157.8(2) . .
C19 C14 N2 C2 96.3(4) . 2_666
C15 C14 N2 C2 -85.0(4) . 2_666
C19 C14 N2 Pd1 -78.6(4) . .
C15 C14 N2 Pd1 100.2(3) . .
C11 C10 O1 Pd1 4.4(6) . .
C9 C10 O1 Pd1 -175.1(3) . .
C11 C12 O2 Pd1 -4.1(7) . .
C13 C12 O2 Pd1 177.1(3) . .
C16 C17 O3 C20 -169.9(4) . .
C18 C17 O3 C20 9.5(6) . .
C2 N2 Pd1 N1 21.4(3) 2_666 .
C14 N2 Pd1 N1 -164.2(2) . .
C2 N2 Pd1 O1 -92.7(9) 2_666 .
C14 N2 Pd1 O1 81.7(9) . .
C2 N2 Pd1 O2 -162.4(3) 2_666 .
C14 N2 Pd1 O2 12.0(2) . .
C1 N1 Pd1 N2 -24.5(3) . .
C8 N1 Pd1 N2 176.4(3) . .
C1 N1 Pd1 O1 148.8(3) . .
C8 N1 Pd1 O1 -10.3(3) . .
C1 N1 Pd1 O2 -118.5(16) . .
C8 N1 Pd1 O2 82.4(17) . .
C10 O1 Pd1 N2 -76.8(9) . .
C10 O1 Pd1 N1 169.2(3) . .
C10 O1 Pd1 O2 -7.1(3) . .
C12 O2 Pd1 N2 -180.0(3) . .
C12 O2 Pd1 N1 -85.9(17) . .
C12 O2 Pd1 O1 6.9(3) . .
