#------------------------------------------------------------------------------
#$Date: 2021-09-06 15:02:30 +0300 (Mon, 06 Sep 2021) $
#$Revision: 268866 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/08/7060878.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_7060878
loop_
_publ_author_name
'Vicente, Ramon'
'Tubau, Ànnia'
'Speed, Saskia'
'Mautner, Franz A.'
'Bierbaumer, Florian'
'Fischer, Roland C.'
'Massoud, Salah S.'
_publ_section_title
;
 Slow magnetic relaxation and luminescence properties in
 neodymium(iii)-4,4,4-trifluoro-1-(2-naphthyl)butane-1,3-dionato complexes
 incorporating bipyridyl ligands
;
_journal_issue                   32
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14713
_journal_page_last               14723
_journal_paper_doi               10.1039/D1NJ02583J
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C52 H32 F9 N2 Nd O6'
_chemical_formula_sum            'C52 H32 F9 N2 Nd O6'
_chemical_formula_weight         1096.03
_chemical_name_common            '[Nd(L)3(bipy)]'
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2021-04-06 deposited with the CCDC.	2021-07-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.036(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.1855(5)
_cell_length_b                   23.2671(8)
_cell_length_c                   17.8776(6)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.00
_cell_measurement_theta_min      2.40
_cell_volume                     4617.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω-scans
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0745
_diffrn_reflns_av_unetI/netI     0.0560
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            116509
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.273
_diffrn_reflns_theta_min         2.296
_exptl_absorpt_coefficient_mu    1.214
_exptl_absorpt_correction_T_max  0.8423
_exptl_absorpt_correction_T_min  0.7142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_description       prism
_exptl_crystal_F_000             2188
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.584
_refine_diff_density_min         -0.696
_refine_diff_density_rms         0.104
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     631
_refine_ls_number_reflns         13743
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0356
_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)+(0.0215P)²+2.2910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0630
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10797
_reflns_number_total             13743
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj02583j2.cif
_cod_data_source_block           rf1619a
_cod_depositor_comments
'Adding full bibliography for 7060876--7060881.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7060878
_shelx_shelxl_version_number     2016/6
_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_min   0.751
_shelx_estimated_absorpt_t_max   0.802
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_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
Nd1 Nd 0.24244(2) 0.46372(2) 0.21126(2) 0.01188(4) Uani 1 1 d . . . . .
C1 C -0.0685(2) 0.49811(10) 0.36564(13) 0.0224(5) Uani 1 1 d . . . . .
N1 N 0.22756(17) 0.47601(8) 0.06421(10) 0.0175(4) Uani 1 1 d . . . . .
F1 F -0.01467(15) 0.46473(6) 0.42041(8) 0.0374(4) Uani 1 1 d . . . . .
O1 O 0.08314(14) 0.47336(6) 0.29246(8) 0.0174(3) Uani 1 1 d . . . . .
F2 F -0.11346(15) 0.54358(6) 0.39866(9) 0.0370(4) Uani 1 1 d . . . . .
C2 C 0.01596(19) 0.51417(9) 0.30772(11) 0.0148(4) Uani 1 1 d . . . . .
N2 N 0.06025(16) 0.41620(8) 0.12781(9) 0.0163(4) Uani 1 1 d . . . . .
O2 O 0.13595(13) 0.55238(6) 0.18687(8) 0.0163(3) Uani 1 1 d . . . . .
O3 O 0.39592(13) 0.40288(6) 0.17082(8) 0.0178(3) Uani 1 1 d . . . . .
C3 C 0.00754(19) 0.56938(9) 0.27890(12) 0.0156(4) Uani 1 1 d . . . . .
H3 H -0.045556 0.595948 0.298098 0.019 Uiso 1 1 calc R U . . .
F3 F -0.16269(13) 0.46797(6) 0.33206(9) 0.0336(4) Uani 1 1 d . . . . .
F4 F 0.63544(12) 0.30569(6) 0.20944(7) 0.0258(3) Uani 1 1 d . . . . .
C4 C 0.07600(18) 0.58736(9) 0.22150(11) 0.0131(4) Uani 1 1 d . . . . .
O4 O 0.22733(13) 0.36895(6) 0.26567(8) 0.0149(3) Uani 1 1 d . . . . .
O6 O 0.37636(13) 0.46645(6) 0.32579(8) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.18176(19) 0.66497(9) 0.16469(11) 0.0142(4) Uani 1 1 d . . . . .
H6 H 0.236354 0.636279 0.152137 0.017 Uiso 1 1 calc R U . . .
F6 F 0.56621(13) 0.34503(7) 0.10410(7) 0.0338(4) Uani 1 1 d . . . . .
O5 O 0.39365(14) 0.53618(6) 0.20273(8) 0.0198(3) Uani 1 1 d . . . . .
F5 F 0.64871(12) 0.39745(6) 0.19542(8) 0.0325(3) Uani 1 1 d . . . . .
C5 C 0.08498(19) 0.64900(9) 0.20115(11) 0.0135(4) Uani 1 1 d . . . . .
F7 F 0.66968(14) 0.60765(8) 0.24283(10) 0.0551(5) Uani 1 1 d . . . . .
C7 C 0.20180(19) 0.72271(9) 0.14555(11) 0.0144(4) Uani 1 1 d . . . . .
F9 F 0.49945(14) 0.64583(6) 0.20330(9) 0.0378(4) Uani 1 1 d . . . . .
C9 C 0.3165(2) 0.79502(10) 0.08872(13) 0.0249(5) Uani 1 1 d . . . . .
H9 H 0.381976 0.805432 0.062312 0.030 Uiso 1 1 calc R U . . .
F8 F 0.57597(16) 0.58343(7) 0.13577(9) 0.0491(5) Uani 1 1 d . . . . .
C8 C 0.3008(2) 0.73882(10) 0.10730(12) 0.0198(5) Uani 1 1 d . . . . .
H8 H 0.356030 0.710480 0.094642 0.024 Uiso 1 1 calc R U . . .
C10 C 0.2368(2) 0.83759(10) 0.10829(13) 0.0266(6) Uani 1 1 d . . . . .
H10 H 0.249376 0.876543 0.095356 0.032 Uiso 1 1 calc R U . . .
C11 C 0.1415(2) 0.82354(10) 0.14571(13) 0.0224(5) Uani 1 1 d . . . . .
H11 H 0.088625 0.852829 0.158712 0.027 Uiso 1 1 calc R U . . .
C13 C 0.0215(2) 0.74852(9) 0.20322(12) 0.0185(5) Uani 1 1 d . . . . .
H13 H -0.033220 0.776832 0.216710 0.022 Uiso 1 1 calc R U . . .
C12 C 0.1207(2) 0.76545(9) 0.16543(11) 0.0167(5) Uani 1 1 d . . . . .
C14 C 0.00365(19) 0.69207(9) 0.22043(11) 0.0162(4) Uani 1 1 d . . . . .
H14 H -0.063372 0.681570 0.245371 0.019 Uiso 1 1 calc R U . . .
C15 C 0.5762(2) 0.35198(10) 0.17906(12) 0.0209(5) Uani 1 1 d . . . . .
C16 C 0.45342(19) 0.36181(9) 0.20604(11) 0.0153(4) Uani 1 1 d . . . . .
C18 C 0.30827(19) 0.33400(9) 0.29235(11) 0.0137(4) Uani 1 1 d . . . . .
C17 C 0.42059(19) 0.32836(9) 0.26346(11) 0.0159(4) Uani 1 1 d . . . . .
H17 H 0.475662 0.300051 0.284922 0.019 Uiso 1 1 calc R U . . .
C19 C 0.28348(19) 0.29904(9) 0.35884(11) 0.0149(4) Uani 1 1 d . . . . .
C20 C 0.19987(19) 0.31921(9) 0.40300(11) 0.0154(4) Uani 1 1 d . . . . .
H20 H 0.156613 0.353372 0.388454 0.018 Uiso 1 1 calc R U . . .
C21 C 0.1767(2) 0.29041(10) 0.46941(12) 0.0184(5) Uani 1 1 d . . . . .
C22 C 0.0938(2) 0.31176(11) 0.51634(12) 0.0252(5) Uani 1 1 d . . . . .
H22 H 0.048589 0.345436 0.502085 0.030 Uiso 1 1 calc R U . . .
C23 C 0.0780(2) 0.28414(12) 0.58242(14) 0.0342(6) Uani 1 1 d . . . . .
H23 H 0.021568 0.298615 0.613298 0.041 Uiso 1 1 calc R U . . .
C24 C 0.1452(2) 0.23447(12) 0.60454(14) 0.0338(7) Uani 1 1 d . . . . .
H24 H 0.135543 0.216437 0.651089 0.041 Uiso 1 1 calc R U . . .
C25 C 0.2241(2) 0.21194(11) 0.55988(13) 0.0278(6) Uani 1 1 d . . . . .
H25 H 0.267876 0.178076 0.575191 0.033 Uiso 1 1 calc R U . . .
C26 C 0.2412(2) 0.23888(10) 0.49055(12) 0.0202(5) Uani 1 1 d . . . . .
C27 C 0.3238(2) 0.21785(10) 0.44307(13) 0.0247(5) Uani 1 1 d . . . . .
H27 H 0.365269 0.182876 0.455658 0.030 Uiso 1 1 calc R U . . .
C28 C 0.3451(2) 0.24681(9) 0.37953(13) 0.0196(5) Uani 1 1 d . . . . .
H28 H 0.401557 0.231958 0.348904 0.024 Uiso 1 1 calc R U . . .
C29 C 0.5613(2) 0.59653(11) 0.20701(14) 0.0265(6) Uani 1 1 d . . . . .
C30 C 0.4916(2) 0.54893(9) 0.24293(12) 0.0176(5) Uani 1 1 d . . . . .
C31 C 0.5406(2) 0.52701(9) 0.31102(12) 0.0193(5) Uani 1 1 d . . . . .
H31 H 0.617535 0.540243 0.332638 0.023 Uiso 1 1 calc R U . . .
C32 C 0.47996(19) 0.48507(9) 0.35029(11) 0.0148(4) Uani 1 1 d . . . . .
C33 C 0.53736(19) 0.46067(9) 0.42332(11) 0.0140(4) Uani 1 1 d . . . . .
C34 C 0.47895(19) 0.41708(9) 0.45569(11) 0.0149(4) Uani 1 1 d . . . . .
H34 H 0.402251 0.404846 0.432430 0.018 Uiso 1 1 calc R U . . .
C35 C 0.53029(19) 0.38985(9) 0.52302(11) 0.0161(4) Uani 1 1 d . . . . .
C36 C 0.4709(2) 0.34432(10) 0.55594(12) 0.0213(5) Uani 1 1 d . . . . .
H36 H 0.392539 0.333100 0.534267 0.026 Uiso 1 1 calc R U . . .
C37 C 0.5244(2) 0.31629(10) 0.61840(13) 0.0263(6) Uani 1 1 d . . . . .
H37 H 0.483873 0.285594 0.639657 0.032 Uiso 1 1 calc R U . . .
C38 C 0.6407(2) 0.33324(11) 0.65128(13) 0.0276(6) Uani 1 1 d . . . . .
H38 H 0.678529 0.313377 0.694238 0.033 Uiso 1 1 calc R U . . .
C39 C 0.6991(2) 0.37788(10) 0.62181(12) 0.0244(5) Uani 1 1 d . . . . .
H39 H 0.776449 0.389129 0.645067 0.029 Uiso 1 1 calc R U . . .
C40 C 0.64562(19) 0.40768(10) 0.55693(12) 0.0173(5) Uani 1 1 d . . . . .
C41 C 0.70290(19) 0.45443(10) 0.52426(12) 0.0187(5) Uani 1 1 d . . . . .
H41 H 0.778649 0.467792 0.547633 0.022 Uiso 1 1 calc R U . . .
C42 C 0.65083(19) 0.48035(10) 0.45995(12) 0.0169(5) Uani 1 1 d . . . . .
H42 H 0.690230 0.511716 0.439337 0.020 Uiso 1 1 calc R U . . .
C43 C 0.3110(2) 0.50739(11) 0.03465(13) 0.0252(5) Uani 1 1 d . . . . .
H43 H 0.375254 0.523290 0.067926 0.030 Uiso 1 1 calc R U . . .
C44 C 0.3083(2) 0.51775(11) -0.04177(13) 0.0301(6) Uani 1 1 d . . . . .
H44 H 0.369513 0.539837 -0.060536 0.036 Uiso 1 1 calc R U . . .
C45 C 0.2144(3) 0.49520(12) -0.08991(13) 0.0341(7) Uani 1 1 d . . . . .
H45 H 0.209176 0.502029 -0.142601 0.041 Uiso 1 1 calc R U . . .
C46 C 0.1281(2) 0.46260(12) -0.06078(13) 0.0319(6) Uani 1 1 d . . . . .
H46 H 0.062967 0.446771 -0.093400 0.038 Uiso 1 1 calc R U . . .
C47 C 0.1367(2) 0.45292(10) 0.01667(12) 0.0204(5) Uani 1 1 d . . . . .
C48 C 0.0481(2) 0.41754(10) 0.05153(12) 0.0215(5) Uani 1 1 d . . . . .
C49 C -0.0422(2) 0.38623(13) 0.00918(14) 0.0363(7) Uani 1 1 d . . . . .
H49 H -0.050269 0.387650 -0.044308 0.044 Uiso 1 1 calc R U . . .
C50 C -0.1199(2) 0.35312(13) 0.04528(15) 0.0395(7) Uani 1 1 d . . . . .
H50 H -0.181023 0.331247 0.016697 0.047 Uiso 1 1 calc R U . . .
C51 C -0.1086(2) 0.35184(11) 0.12308(14) 0.0278(6) Uani 1 1 d . . . . .
H51 H -0.161340 0.329441 0.149042 0.033 Uiso 1 1 calc R U . . .
C52 C -0.0174(2) 0.38447(10) 0.16193(13) 0.0200(5) Uani 1 1 d . . . . .
H52 H -0.009491 0.384345 0.215442 0.024 Uiso 1 1 calc R U . . .
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'
Nd Nd -0.1943 3.0179 '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
O6 Nd1 O2 112.29(5) . . ?
O6 Nd1 O3 82.95(5) . . ?
O2 Nd1 O3 144.09(5) . . ?
O6 Nd1 O5 70.32(5) . . ?
O2 Nd1 O5 73.90(5) . . ?
O3 Nd1 O5 81.96(5) . . ?
O6 Nd1 O4 75.36(5) . . ?
O2 Nd1 O4 143.02(5) . . ?
O3 Nd1 O4 70.89(5) . . ?
O5 Nd1 O4 138.32(5) . . ?
O6 Nd1 O1 85.10(5) . . ?
O2 Nd1 O1 69.29(5) . . ?
O3 Nd1 O1 146.38(5) . . ?
O5 Nd1 O1 122.88(5) . . ?
O4 Nd1 O1 75.72(5) . . ?
O6 Nd1 N2 149.72(5) . . ?
O2 Nd1 N2 85.70(5) . . ?
O3 Nd1 N2 96.58(5) . . ?
O5 Nd1 N2 139.80(5) . . ?
O4 Nd1 N2 75.93(5) . . ?
O1 Nd1 N2 78.69(5) . . ?
O6 Nd1 N1 144.25(6) . . ?
O2 Nd1 N1 75.82(5) . . ?
O3 Nd1 N1 73.94(5) . . ?
O5 Nd1 N1 79.58(5) . . ?
O4 Nd1 N1 120.08(5) . . ?
O1 Nd1 N1 128.52(5) . . ?
N2 Nd1 N1 61.75(6) . . ?
F1 C1 F2 107.24(19) . . ?
F1 C1 F3 106.41(19) . . ?
F2 C1 F3 107.03(19) . . ?
F1 C1 C2 112.21(19) . . ?
F2 C1 C2 113.68(19) . . ?
F3 C1 C2 109.88(18) . . ?
C43 N1 C47 118.25(19) . . ?
C43 N1 Nd1 119.38(14) . . ?
C47 N1 Nd1 122.36(14) . . ?
C2 O1 Nd1 134.03(14) . . ?
O1 C2 C3 129.3(2) . . ?
O1 C2 C1 113.33(19) . . ?
C3 C2 C1 117.33(19) . . ?
C52 N2 C48 118.69(19) . . ?
C52 N2 Nd1 118.36(13) . . ?
C48 N2 Nd1 122.61(15) . . ?
C4 O2 Nd1 138.35(13) . . ?
C16 O3 Nd1 128.96(13) . . ?
C2 C3 C4 121.7(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
O2 C4 C3 122.08(19) . . ?
O2 C4 C5 116.46(18) . . ?
C3 C4 C5 121.40(19) . . ?
C18 O4 Nd1 130.82(13) . . ?
C32 O6 Nd1 139.41(14) . . ?
C5 C6 C7 121.8(2) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C30 O5 Nd1 133.81(14) . . ?
C6 C5 C14 119.06(19) . . ?
C6 C5 C4 117.11(19) . . ?
C14 C5 C4 123.75(19) . . ?
C6 C7 C12 118.7(2) . . ?
C6 C7 C8 121.6(2) . . ?
C12 C7 C8 119.6(2) . . ?
C8 C9 C10 120.6(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C8 C7 120.1(2) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 120.7(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C14 C13 C12 121.0(2) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C7 C12 C11 118.3(2) . . ?
C7 C12 C13 118.94(19) . . ?
C11 C12 C13 122.7(2) . . ?
C13 C14 C5 120.4(2) . . ?
C13 C14 H14 119.8 . . ?
C5 C14 H14 119.8 . . ?
F6 C15 F4 106.49(18) . . ?
F6 C15 F5 106.68(18) . . ?
F4 C15 F5 106.78(18) . . ?
F6 C15 C16 111.43(18) . . ?
F4 C15 C16 114.22(18) . . ?
F5 C15 C16 110.83(18) . . ?
O3 C16 C17 129.0(2) . . ?
O3 C16 C15 112.04(18) . . ?
C17 C16 C15 118.95(19) . . ?
O4 C18 C17 123.06(19) . . ?
O4 C18 C19 117.10(19) . . ?
C17 C18 C19 119.82(18) . . ?
C16 C17 C18 123.24(19) . . ?
C16 C17 H17 118.4 . . ?
C18 C17 H17 118.4 . . ?
C20 C19 C28 118.9(2) . . ?
C20 C19 C18 118.40(19) . . ?
C28 C19 C18 122.7(2) . . ?
C19 C20 C21 121.7(2) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C20 C21 C22 122.1(2) . . ?
C20 C21 C26 118.8(2) . . ?
C22 C21 C26 119.0(2) . . ?
C23 C22 C21 120.5(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 120.3(3) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C25 C24 C23 120.8(2) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 120.4(2) . . ?
C24 C25 H25 119.8 . . ?
C26 C25 H25 119.8 . . ?
C27 C26 C25 122.5(2) . . ?
C27 C26 C21 118.5(2) . . ?
C25 C26 C21 119.0(2) . . ?
C28 C27 C26 121.4(2) . . ?
C28 C27 H27 119.3 . . ?
C26 C27 H27 119.3 . . ?
C27 C28 C19 120.6(2) . . ?
C27 C28 H28 119.7 . . ?
C19 C28 H28 119.7 . . ?
F7 C29 F9 107.1(2) . . ?
F7 C29 F8 107.0(2) . . ?
F9 C29 F8 105.73(19) . . ?
F7 C29 C30 114.77(19) . . ?
F9 C29 C30 110.7(2) . . ?
F8 C29 C30 111.1(2) . . ?
O5 C30 C31 129.8(2) . . ?
O5 C30 C29 112.20(19) . . ?
C31 C30 C29 118.0(2) . . ?
C30 C31 C32 122.0(2) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
O6 C32 C31 122.46(19) . . ?
O6 C32 C33 116.75(19) . . ?
C31 C32 C33 120.79(19) . . ?
C34 C33 C42 119.02(19) . . ?
C34 C33 C32 118.25(18) . . ?
C42 C33 C32 122.7(2) . . ?
C33 C34 C35 121.60(19) . . ?
C33 C34 H34 119.2 . . ?
C35 C34 H34 119.2 . . ?
C36 C35 C34 121.66(19) . . ?
C36 C35 C40 119.31(19) . . ?
C34 C35 C40 119.0(2) . . ?
C37 C36 C35 121.0(2) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 119.7(2) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C39 C38 C37 120.6(2) . . ?
C39 C38 H38 119.7 . . ?
C37 C38 H38 119.7 . . ?
C38 C39 C40 120.9(2) . . ?
C38 C39 H39 119.6 . . ?
C40 C39 H39 119.6 . . ?
C39 C40 C35 118.5(2) . . ?
C39 C40 C41 122.9(2) . . ?
C35 C40 C41 118.65(19) . . ?
C42 C41 C40 121.1(2) . . ?
C42 C41 H41 119.5 . . ?
C40 C41 H41 119.5 . . ?
C41 C42 C33 120.5(2) . . ?
C41 C42 H42 119.7 . . ?
C33 C42 H42 119.7 . . ?
N1 C43 C44 123.4(2) . . ?
N1 C43 H43 118.3 . . ?
C44 C43 H43 118.3 . . ?
C45 C44 C43 118.3(2) . . ?
C45 C44 H44 120.9 . . ?
C43 C44 H44 120.9 . . ?
C46 C45 C44 119.3(2) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 119.8(2) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
N1 C47 C46 120.9(2) . . ?
N1 C47 C48 116.45(19) . . ?
C46 C47 C48 122.6(2) . . ?
N2 C48 C49 120.8(2) . . ?
N2 C48 C47 116.53(19) . . ?
C49 C48 C47 122.7(2) . . ?
C50 C49 C48 119.7(2) . . ?
C50 C49 H49 120.2 . . ?
C48 C49 H49 120.2 . . ?
C49 C50 C51 119.9(2) . . ?
C49 C50 H50 120.1 . . ?
C51 C50 H50 120.1 . . ?
C50 C51 C52 117.6(2) . . ?
C50 C51 H51 121.2 . . ?
C52 C51 H51 121.2 . . ?
N2 C52 C51 123.4(2) . . ?
N2 C52 H52 118.3 . . ?
C51 C52 H52 118.3 . . ?
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
Nd1 O6 2.3851(13) . ?
Nd1 O2 2.3953(14) . ?
Nd1 O3 2.4037(15) . ?
Nd1 O5 2.4063(15) . ?
Nd1 O4 2.4241(14) . ?
Nd1 O1 2.4425(15) . ?
Nd1 N2 2.6185(17) . ?
Nd1 N1 2.6294(17) . ?
C1 F1 1.334(3) . ?
C1 F2 1.339(3) . ?
C1 F3 1.344(3) . ?
C1 C2 1.531(3) . ?
N1 C43 1.343(3) . ?
N1 C47 1.354(3) . ?
O1 C2 1.261(3) . ?
C2 C3 1.383(3) . ?
N2 C52 1.342(3) . ?
N2 C48 1.354(3) . ?
O2 C4 1.264(2) . ?
O3 C16 1.274(2) . ?
C3 C4 1.417(3) . ?
C3 H3 0.9500 . ?
F4 C15 1.344(2) . ?
C4 C5 1.486(3) . ?
O4 C18 1.266(2) . ?
O6 C32 1.264(2) . ?
C6 C5 1.381(3) . ?
C6 C7 1.411(3) . ?
C6 H6 0.9500 . ?
F6 C15 1.341(2) . ?
O5 C30 1.269(3) . ?
F5 C15 1.343(3) . ?
C5 C14 1.424(3) . ?
F7 C29 1.326(3) . ?
C7 C12 1.420(3) . ?
C7 C8 1.421(3) . ?
F9 C29 1.337(3) . ?
C9 C8 1.366(3) . ?
C9 C10 1.405(3) . ?
C9 H9 0.9500 . ?
F8 C29 1.339(3) . ?
C8 H8 0.9500 . ?
C10 C11 1.366(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.423(3) . ?
C11 H11 0.9500 . ?
C13 C14 1.369(3) . ?
C13 C12 1.424(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.528(3) . ?
C16 C17 1.374(3) . ?
C18 C17 1.422(3) . ?
C18 C19 1.494(3) . ?
C17 H17 0.9500 . ?
C19 C20 1.378(3) . ?
C19 C28 1.424(3) . ?
C20 C21 1.415(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(3) . ?
C21 C26 1.426(3) . ?
C22 C23 1.375(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.409(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.365(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.422(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.416(3) . ?
C27 C28 1.367(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 C30 1.539(3) . ?
C30 C31 1.371(3) . ?
C31 C32 1.422(3) . ?
C31 H31 0.9500 . ?
C32 C33 1.495(3) . ?
C33 C34 1.372(3) . ?
C33 C42 1.430(3) . ?
C34 C35 1.418(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.417(3) . ?
C35 C40 1.419(3) . ?
C36 C37 1.367(3) . ?
C36 H36 0.9500 . ?
C37 C38 1.416(3) . ?
C37 H37 0.9500 . ?
C38 C39 1.366(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.419(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.423(3) . ?
C41 C42 1.364(3) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.384(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.377(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.379(4) . ?
C45 H45 0.9500 . ?
C46 C47 1.395(3) . ?
C46 H46 0.9500 . ?
C47 C48 1.483(3) . ?
C48 C49 1.392(3) . ?
C49 C50 1.379(4) . ?
C49 H49 0.9500 . ?
C50 C51 1.381(3) . ?
C50 H50 0.9500 . ?
C51 C52 1.388(3) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
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
Nd1 O1 C2 C3 3.2(3) . . . . ?
Nd1 O1 C2 C1 -178.05(13) . . . . ?
F1 C1 C2 O1 39.5(3) . . . . ?
F2 C1 C2 O1 161.37(19) . . . . ?
F3 C1 C2 O1 -78.7(2) . . . . ?
F1 C1 C2 C3 -141.61(19) . . . . ?
F2 C1 C2 C3 -19.7(3) . . . . ?
F3 C1 C2 C3 100.2(2) . . . . ?
O1 C2 C3 C4 2.9(3) . . . . ?
C1 C2 C3 C4 -175.83(19) . . . . ?
Nd1 O2 C4 C3 -31.1(3) . . . . ?
Nd1 O2 C4 C5 146.44(15) . . . . ?
C2 C3 C4 O2 9.4(3) . . . . ?
C2 C3 C4 C5 -167.99(19) . . . . ?
C7 C6 C5 C14 -0.4(3) . . . . ?
C7 C6 C5 C4 -177.35(17) . . . . ?
O2 C4 C5 C6 -18.7(3) . . . . ?
C3 C4 C5 C6 158.80(19) . . . . ?
O2 C4 C5 C14 164.51(18) . . . . ?
C3 C4 C5 C14 -17.9(3) . . . . ?
C5 C6 C7 C12 0.9(3) . . . . ?
C5 C6 C7 C8 -179.30(19) . . . . ?
C10 C9 C8 C7 1.2(3) . . . . ?
C6 C7 C8 C9 179.1(2) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
C6 C7 C12 C11 -179.85(18) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C6 C7 C12 C13 -0.6(3) . . . . ?
C8 C7 C12 C13 179.52(18) . . . . ?
C10 C11 C12 C7 0.3(3) . . . . ?
C10 C11 C12 C13 -178.9(2) . . . . ?
C14 C13 C12 C7 0.0(3) . . . . ?
C14 C13 C12 C11 179.2(2) . . . . ?
C12 C13 C14 C5 0.4(3) . . . . ?
C6 C5 C14 C13 -0.2(3) . . . . ?
C4 C5 C14 C13 176.49(19) . . . . ?
Nd1 O3 C16 C17 23.8(3) . . . . ?
Nd1 O3 C16 C15 -154.42(14) . . . . ?
F6 C15 C16 O3 -53.3(2) . . . . ?
F4 C15 C16 O3 -174.02(18) . . . . ?
F5 C15 C16 O3 65.3(2) . . . . ?
F6 C15 C16 C17 128.3(2) . . . . ?
F4 C15 C16 C17 7.5(3) . . . . ?
F5 C15 C16 C17 -113.1(2) . . . . ?
Nd1 O4 C18 C17 -33.9(3) . . . . ?
Nd1 O4 C18 C19 144.06(14) . . . . ?
O3 C16 C17 C18 2.1(4) . . . . ?
C15 C16 C17 C18 -179.76(19) . . . . ?
O4 C18 C17 C16 2.6(3) . . . . ?
C19 C18 C17 C16 -175.3(2) . . . . ?
O4 C18 C19 C20 -22.4(3) . . . . ?
C17 C18 C19 C20 155.59(19) . . . . ?
O4 C18 C19 C28 159.44(19) . . . . ?
C17 C18 C19 C28 -22.5(3) . . . . ?
C28 C19 C20 C21 2.1(3) . . . . ?
C18 C19 C20 C21 -176.12(19) . . . . ?
C19 C20 C21 C22 178.0(2) . . . . ?
C19 C20 C21 C26 -0.6(3) . . . . ?
C20 C21 C22 C23 -176.7(2) . . . . ?
C26 C21 C22 C23 1.8(3) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 -2.0(4) . . . . ?
C23 C24 C25 C26 1.0(4) . . . . ?
C24 C25 C26 C27 178.6(2) . . . . ?
C24 C25 C26 C21 1.4(3) . . . . ?
C20 C21 C26 C27 -1.5(3) . . . . ?
C22 C21 C26 C27 179.9(2) . . . . ?
C20 C21 C26 C25 175.8(2) . . . . ?
C22 C21 C26 C25 -2.8(3) . . . . ?
C25 C26 C27 C28 -175.1(2) . . . . ?
C21 C26 C27 C28 2.1(3) . . . . ?
C26 C27 C28 C19 -0.6(3) . . . . ?
C20 C19 C28 C27 -1.5(3) . . . . ?
C18 C19 C28 C27 176.6(2) . . . . ?
Nd1 O5 C30 C31 -5.9(4) . . . . ?
Nd1 O5 C30 C29 174.34(14) . . . . ?
F7 C29 C30 O5 -173.7(2) . . . . ?
F9 C29 C30 O5 65.0(3) . . . . ?
F8 C29 C30 O5 -52.1(3) . . . . ?
F7 C29 C30 C31 6.5(3) . . . . ?
F9 C29 C30 C31 -114.8(2) . . . . ?
F8 C29 C30 C31 128.1(2) . . . . ?
O5 C30 C31 C32 -3.0(4) . . . . ?
C29 C30 C31 C32 176.7(2) . . . . ?
Nd1 O6 C32 C31 16.9(3) . . . . ?
Nd1 O6 C32 C33 -162.91(14) . . . . ?
C30 C31 C32 O6 -1.6(3) . . . . ?
C30 C31 C32 C33 178.1(2) . . . . ?
O6 C32 C33 C34 4.9(3) . . . . ?
C31 C32 C33 C34 -174.9(2) . . . . ?
O6 C32 C33 C42 -175.97(19) . . . . ?
C31 C32 C33 C42 4.2(3) . . . . ?
C42 C33 C34 C35 -2.2(3) . . . . ?
C32 C33 C34 C35 176.95(19) . . . . ?
C33 C34 C35 C36 -179.1(2) . . . . ?
C33 C34 C35 C40 -0.9(3) . . . . ?
C34 C35 C36 C37 176.2(2) . . . . ?
C40 C35 C36 C37 -2.0(3) . . . . ?
C35 C36 C37 C38 0.6(4) . . . . ?
C36 C37 C38 C39 1.0(4) . . . . ?
C37 C38 C39 C40 -1.1(4) . . . . ?
C38 C39 C40 C35 -0.3(3) . . . . ?
C38 C39 C40 C41 180.0(2) . . . . ?
C36 C35 C40 C39 1.8(3) . . . . ?
C34 C35 C40 C39 -176.4(2) . . . . ?
C36 C35 C40 C41 -178.5(2) . . . . ?
C34 C35 C40 C41 3.3(3) . . . . ?
C39 C40 C41 C42 177.1(2) . . . . ?
C35 C40 C41 C42 -2.6(3) . . . . ?
C40 C41 C42 C33 -0.6(3) . . . . ?
C34 C33 C42 C41 3.0(3) . . . . ?
C32 C33 C42 C41 -176.12(19) . . . . ?
C47 N1 C43 C44 0.6(4) . . . . ?
Nd1 N1 C43 C44 -177.82(19) . . . . ?
N1 C43 C44 C45 0.7(4) . . . . ?
C43 C44 C45 C46 -1.0(4) . . . . ?
C44 C45 C46 C47 0.1(4) . . . . ?
C43 N1 C47 C46 -1.6(3) . . . . ?
Nd1 N1 C47 C46 176.80(17) . . . . ?
C43 N1 C47 C48 178.7(2) . . . . ?
Nd1 N1 C47 C48 -2.9(3) . . . . ?
C45 C46 C47 N1 1.3(4) . . . . ?
C45 C46 C47 C48 -179.0(2) . . . . ?
C52 N2 C48 C49 -0.6(3) . . . . ?
Nd1 N2 C48 C49 172.52(18) . . . . ?
C52 N2 C48 C47 -179.6(2) . . . . ?
Nd1 N2 C48 C47 -6.5(3) . . . . ?
N1 C47 C48 N2 6.0(3) . . . . ?
C46 C47 C48 N2 -173.7(2) . . . . ?
N1 C47 C48 C49 -173.0(2) . . . . ?
C46 C47 C48 C49 7.3(4) . . . . ?
N2 C48 C49 C50 -0.4(4) . . . . ?
C47 C48 C49 C50 178.5(2) . . . . ?
C48 C49 C50 C51 0.8(4) . . . . ?
C49 C50 C51 C52 -0.2(4) . . . . ?
C48 N2 C52 C51 1.3(3) . . . . ?
Nd1 N2 C52 C51 -172.14(18) . . . . ?
C50 C51 C52 N2 -0.9(4) . . . . ?
