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#$Date: 2022-01-19 11:58:36 +0200 (Wed, 19 Jan 2022) $
#$Revision: 272129 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/60/1566042.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_1566042
loop_
_publ_author_name
'Mautner, Franz A.'
'Bierbaumer, Florian'
'Fischer, Roland C.'
'Vicente, Ramon'
'Tubau, Ànnia'
'Ferran, Arnau'
'Massoud, Salah S.'
_publ_section_title
;
 Structural Characterization, Magnetic and Luminescent Properties of
 Praseodymium(III)-4,4,4-Trifluoro-1-(2-Naphthyl)Butane-1,3-Dionato(1-)
 Complexes
;
_journal_issue                   2
_journal_name_full               Crystals
_journal_page_first              179
_journal_paper_doi               10.3390/cryst11020179
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C54 H36 F9 N2 O6 Pr'
_chemical_formula_sum            'C54 H36 F9 N2 O6 Pr'
_chemical_formula_weight         1120.76
_chemical_name_common            '[PrL3(5,5'-Me2bipy)]'
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.1848(6)
_cell_length_b                   11.9034(3)
_cell_length_c                   19.6102(6)
_cell_measurement_reflns_used    9093
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.65
_cell_measurement_theta_min      2.24
_cell_volume                     4711.7(2)
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.0648
_diffrn_reflns_av_unetI/netI     0.0381
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            163636
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        29.995
_diffrn_reflns_theta_max         29.995
_diffrn_reflns_theta_min         2.241
_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_T_max  0.9003
_exptl_absorpt_correction_T_min  0.7325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.580
_exptl_crystal_description       prism
_exptl_crystal_F_000             2248
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.967
_refine_diff_density_min         -0.784
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 5440 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     651
_refine_ls_number_reflns         13727
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.058
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0155P)²+2.4449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0509
_refine_ls_wR_factor_ref         0.0534
_reflns_Friedel_coverage         0.946
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                12338
_reflns_number_total             13727
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            Crystals-2021-11-2-179.cif
_cod_data_source_block           rf1690
_cod_database_code               1566042
_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   0.766
_shelx_estimated_absorpt_t_max   0.868
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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
Pr1 Pr 0.55141(2) 0.15089(2) 0.53277(2) 0.01127(4) Uani 1 1 d . . . . .
N1 N 0.50391(13) -0.0509(2) 0.50825(13) 0.0174(5) Uani 1 1 d . . . . .
C1 C 0.64482(17) -0.1425(3) 0.66422(17) 0.0204(7) Uani 1 1 d . . . . .
F1 F 0.58369(12) -0.1677(2) 0.68362(14) 0.0443(7) Uani 1 1 d . . . . .
O1 O 0.60259(11) 0.02048(19) 0.61272(11) 0.0176(5) Uani 1 1 d . . . . .
F2 F 0.67630(11) -0.10445(19) 0.71927(10) 0.0308(5) Uani 1 1 d . . . . .
N2 N 0.45006(13) 0.0810(2) 0.60578(14) 0.0173(6) Uani 1 1 d . . . . .
C2 C 0.64519(16) -0.0550(3) 0.60660(16) 0.0160(6) Uani 1 1 d . . . . .
O2 O 0.65298(11) 0.07778(19) 0.48825(11) 0.0171(5) Uani 1 1 d . . . . .
O3 O 0.55136(11) 0.2831(2) 0.62683(11) 0.0171(5) Uani 1 1 d . . . . .
F3 F 0.67469(13) -0.23936(18) 0.64710(11) 0.0363(6) Uani 1 1 d . . . . .
C3 C 0.69306(16) -0.0686(3) 0.55644(16) 0.0180(7) Uani 1 1 d . . . . .
H3 H 0.723742 -0.128877 0.560016 0.022 Uiso 1 1 calc R U . . .
O4 O 0.61296(11) 0.31740(19) 0.50195(11) 0.0172(5) Uani 1 1 d . . . . .
C4 C 0.69712(14) 0.0055(3) 0.49998(16) 0.0142(6) Uani 1 1 d . . . . .
F4 F 0.46671(11) 0.4361(2) 0.69308(13) 0.0430(7) Uani 1 1 d . . . . .
O5 O 0.53829(11) 0.15281(19) 0.40979(12) 0.0171(5) Uani 1 1 d . . . . .
F5 F 0.54836(12) 0.5500(2) 0.70203(13) 0.0437(7) Uani 1 1 d . . . . .
C5 C 0.75426(15) 0.0023(3) 0.45230(16) 0.0137(6) Uani 1 1 d . . . . .
O6 O 0.46261(10) 0.27528(19) 0.50043(11) 0.0165(5) Uani 1 1 d . . . . .
C6 C 0.74899(15) 0.0638(3) 0.39262(16) 0.0150(6) Uani 1 1 d . . . . .
H6 H 0.707628 0.096621 0.380917 0.018 Uiso 1 1 calc R U . . .
F6 F 0.55258(13) 0.3901(2) 0.75071(12) 0.0465(7) Uani 1 1 d . . . . .
F9 F 0.54403(17) 0.3122(3) 0.26105(15) 0.0827(12) Uani 1 1 d . U . . .
C9 C 0.85493(18) 0.1653(3) 0.25040(18) 0.0239(8) Uani 1 1 d . . . . .
H9 H 0.852110 0.212381 0.211373 0.029 Uiso 1 1 calc R U . . .
F8 F 0.62203(10) 0.2195(2) 0.30627(11) 0.0333(5) Uani 1 1 d . . . . .
C8 C 0.79998(17) 0.1475(3) 0.28997(17) 0.0192(7) Uani 1 1 d . . . . .
H8 H 0.759065 0.181523 0.277850 0.023 Uiso 1 1 calc R U . . .
F7 F 0.53682(15) 0.1350(3) 0.26975(14) 0.0698(11) Uani 1 1 d . . . . .
C7 C 0.80368(15) 0.0787(3) 0.34884(16) 0.0152(6) Uani 1 1 d . . . . .
C11 C 0.92077(16) 0.0461(3) 0.32341(18) 0.0228(7) Uani 1 1 d . . . . .
H11 H 0.961935 0.011519 0.333923 0.027 Uiso 1 1 calc R U . . .
C10 C 0.91572(17) 0.1139(3) 0.26754(19) 0.0253(8) Uani 1 1 d . . . . .
H10 H 0.953590 0.126721 0.239839 0.030 Uiso 1 1 calc R U . . .
C12 C 0.86487(15) 0.0268(3) 0.36607(17) 0.0170(7) Uani 1 1 d . . . . .
C13 C 0.86858(15) -0.0399(3) 0.42566(17) 0.0183(7) Uani 1 1 d . . . . .
H13 H 0.908754 -0.077623 0.436310 0.022 Uiso 1 1 calc R U . . .
C15 C 0.53230(18) 0.4431(3) 0.69383(18) 0.0238(7) Uani 1 1 d . . . . .
C14 C 0.81518(15) -0.0510(3) 0.46824(17) 0.0158(6) Uani 1 1 d . . . . .
H14 H 0.818957 -0.094624 0.508626 0.019 Uiso 1 1 calc R U . . .
C16 C 0.56197(15) 0.3885(3) 0.62982(17) 0.0166(6) Uani 1 1 d . . . . .
C17 C 0.59492(16) 0.4572(3) 0.58515(17) 0.0192(7) Uani 1 1 d . . . . .
H17 H 0.599449 0.534640 0.595795 0.023 Uiso 1 1 calc R U . . .
C19 C 0.66541(15) 0.4900(3) 0.47998(17) 0.0165(6) Uani 1 1 d . . . . .
C18 C 0.62271(13) 0.4156(3) 0.52291(18) 0.0154(7) Uani 1 1 d . . . . .
C20 C 0.67981(15) 0.4555(3) 0.41471(17) 0.0173(6) Uani 1 1 d . . . . .
H20 H 0.660699 0.388047 0.397885 0.021 Uiso 1 1 calc R U . . .
C21 C 0.72255(16) 0.5185(3) 0.37207(17) 0.0179(6) Uani 1 1 d . . . . .
C22 C 0.74012(17) 0.4814(3) 0.30566(18) 0.0234(7) Uani 1 1 d . . . . .
H22 H 0.719978 0.415953 0.287247 0.028 Uiso 1 1 calc R U . . .
C23 C 0.78583(18) 0.5392(3) 0.26808(18) 0.0250(8) Uani 1 1 d . . . . .
H23 H 0.797951 0.512930 0.224076 0.030 Uiso 1 1 calc R U . . .
C24 C 0.81511(18) 0.6378(3) 0.29437(19) 0.0243(8) Uani 1 1 d . . . . .
H24 H 0.847340 0.676752 0.268155 0.029 Uiso 1 1 calc R U . . .
C25 C 0.79760(17) 0.6777(3) 0.35700(18) 0.0213(7) Uani 1 1 d . . . . .
H25 H 0.816593 0.745623 0.373308 0.026 Uiso 1 1 calc R U . . .
C26 C 0.75126(16) 0.6188(3) 0.39810(18) 0.0181(6) Uani 1 1 d . . . . .
C27 C 0.73453(17) 0.6534(3) 0.4647(2) 0.0236(7) Uani 1 1 d . . . . .
H27 H 0.752463 0.721456 0.482055 0.028 Uiso 1 1 calc R U . . .
C28 C 0.69325(16) 0.5914(3) 0.50467(18) 0.0220(7) Uani 1 1 d . . . . .
H28 H 0.683024 0.616340 0.549466 0.026 Uiso 1 1 calc R U . . .
C29 C 0.55631(18) 0.2284(4) 0.30163(18) 0.0274(8) Uani 1 1 d . . . . .
C30 C 0.52520(16) 0.2371(3) 0.37291(17) 0.0196(7) Uani 1 1 d . . . . .
C31 C 0.48747(16) 0.3310(3) 0.38818(17) 0.0214(7) Uani 1 1 d . . . . .
H31 H 0.482555 0.387800 0.354547 0.026 Uiso 1 1 calc R U . . .
C32 C 0.45586(15) 0.3454(3) 0.45232(17) 0.0164(6) Uani 1 1 d . . . . .
C33 C 0.41298(15) 0.4448(3) 0.46604(17) 0.0163(6) Uani 1 1 d . . . . .
C34 C 0.38728(13) 0.4577(2) 0.5305(2) 0.0182(5) Uani 1 1 d . . . . .
H34 H 0.397881 0.403900 0.564546 0.022 Uiso 1 1 calc R U . . .
C35 C 0.34562(15) 0.5486(3) 0.54748(15) 0.0180(8) Uani 1 1 d . . . . .
C36 C 0.31890(18) 0.5629(3) 0.61401(18) 0.0233(7) Uani 1 1 d . . . . .
H36 H 0.329706 0.510642 0.648919 0.028 Uiso 1 1 calc R U . . .
C37 C 0.27761(18) 0.6515(3) 0.62821(19) 0.0240(7) Uani 1 1 d . . . . .
H37 H 0.259948 0.660109 0.672815 0.029 Uiso 1 1 calc R U . . .
C38 C 0.26131(17) 0.7297(3) 0.5771(2) 0.0231(7) Uani 1 1 d . . . . .
H38 H 0.232493 0.790502 0.587356 0.028 Uiso 1 1 calc R U . . .
C39 C 0.28653(18) 0.7187(3) 0.51326(18) 0.0229(8) Uani 1 1 d . . . . .
H39 H 0.275131 0.772261 0.479299 0.027 Uiso 1 1 calc R U . . .
C40 C 0.32959(16) 0.6288(3) 0.49640(17) 0.0180(7) Uani 1 1 d . . . . .
C41 C 0.35742(17) 0.6154(3) 0.43021(18) 0.0217(7) Uani 1 1 d . . . . .
H41 H 0.347567 0.668879 0.395718 0.026 Uiso 1 1 calc R U . . .
C42 C 0.39795(16) 0.5271(3) 0.41548(17) 0.0181(7) Uani 1 1 d . . . . .
H42 H 0.416388 0.520345 0.371095 0.022 Uiso 1 1 calc R U . . .
C43 C 0.46620(15) -0.1022(3) 0.55612(17) 0.0176(7) Uani 1 1 d . . . . .
C44 C 0.46130(17) -0.2191(3) 0.55882(19) 0.0233(7) Uani 1 1 d . . . . .
H44 H 0.436447 -0.254528 0.593895 0.028 Uiso 1 1 calc R U . . .
C45 C 0.49287(18) -0.2821(3) 0.51011(19) 0.0262(8) Uani 1 1 d . . . . .
H45 H 0.490638 -0.361793 0.512131 0.031 Uiso 1 1 calc R U . . .
C46 C 0.52809(17) -0.2307(3) 0.45785(19) 0.0232(7) Uani 1 1 d . . . . .
C47 C 0.53322(16) -0.1141(3) 0.46112(18) 0.0201(7) Uani 1 1 d . . . . .
H47 H 0.559325 -0.077427 0.427530 0.024 Uiso 1 1 calc R U . . .
C48 C 0.55863(19) -0.2948(3) 0.3995(2) 0.0330(9) Uani 1 1 d . . . . .
H48A H 0.533640 -0.279897 0.357673 0.049 Uiso 1 1 calc R U . . .
H48B H 0.557410 -0.375457 0.409600 0.049 Uiso 1 1 calc R U . . .
H48C H 0.604698 -0.270874 0.393454 0.049 Uiso 1 1 calc R U . . .
C49 C 0.42989(16) -0.0266(3) 0.60385(17) 0.0177(7) Uani 1 1 d . . . . .
C50 C 0.37654(17) -0.0632(3) 0.64297(19) 0.0257(8) Uani 1 1 d . . . . .
H50 H 0.362430 -0.139248 0.640662 0.031 Uiso 1 1 calc R U . . .
C51 C 0.34432(19) 0.0118(4) 0.6851(2) 0.0287(9) Uani 1 1 d . . . . .
H51 H 0.307758 -0.012680 0.711752 0.034 Uiso 1 1 calc R U . . .
C52 C 0.36495(17) 0.1225(3) 0.68878(19) 0.0246(8) Uani 1 1 d . . . . .
C53 C 0.41822(16) 0.1524(3) 0.64732(18) 0.0219(7) Uani 1 1 d . . . . .
H53 H 0.432895 0.228252 0.648585 0.026 Uiso 1 1 calc R U . . .
C54 C 0.3323(2) 0.2091(4) 0.7337(2) 0.0401(11) Uani 1 1 d . . . . .
H54A H 0.365020 0.265561 0.747366 0.060 Uiso 1 1 calc R U . . .
H54B H 0.314276 0.172388 0.774442 0.060 Uiso 1 1 calc R U . . .
H54C H 0.296271 0.245622 0.708562 0.060 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'
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'
Pr Pr -0.2180 2.8214 '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
O2 Pr1 O6 139.90(8) . .
O2 Pr1 O4 76.49(8) . .
O6 Pr1 O4 79.20(8) . .
O2 Pr1 O3 120.94(8) . .
O6 Pr1 O3 78.52(8) . .
O4 Pr1 O3 70.00(7) . .
O2 Pr1 O5 74.59(7) . .
O6 Pr1 O5 69.60(8) . .
O4 Pr1 O5 78.45(8) . .
O3 Pr1 O5 138.58(8) . .
O2 Pr1 O1 68.88(7) . .
O6 Pr1 O1 151.19(7) . .
O4 Pr1 O1 117.75(8) . .
O3 Pr1 O1 85.66(8) . .
O5 Pr1 O1 133.79(7) . .
O2 Pr1 N1 85.04(8) . .
O6 Pr1 N1 103.99(8) . .
O4 Pr1 N1 152.97(8) . .
O3 Pr1 N1 137.02(8) . .
O5 Pr1 N1 77.71(8) . .
O1 Pr1 N1 71.96(8) . .
O2 Pr1 N2 138.57(8) . .
O6 Pr1 N2 76.06(8) . .
O4 Pr1 N2 142.66(8) . .
O3 Pr1 N2 77.93(8) . .
O5 Pr1 N2 117.31(8) . .
O1 Pr1 N2 77.18(8) . .
N1 Pr1 N2 61.81(9) . .
C47 N1 C43 118.4(3) . .
C47 N1 Pr1 118.8(2) . .
C43 N1 Pr1 119.3(2) . .
F1 C1 F2 106.8(3) . .
F1 C1 F3 107.1(3) . .
F2 C1 F3 106.3(3) . .
F1 C1 C2 111.7(3) . .
F2 C1 C2 111.3(3) . .
F3 C1 C2 113.3(3) . .
C2 O1 Pr1 133.5(2) . .
C53 N2 C49 118.4(3) . .
C53 N2 Pr1 120.2(2) . .
C49 N2 Pr1 121.4(2) . .
O1 C2 C3 129.1(3) . .
O1 C2 C1 114.4(3) . .
C3 C2 C1 116.4(3) . .
C4 O2 Pr1 142.0(2) . .
C16 O3 Pr1 132.4(2) . .
C2 C3 C4 121.4(3) . .
C2 C3 H3 119.3 . .
C4 C3 H3 119.3 . .
C18 O4 Pr1 139.7(2) . .
O2 C4 C3 121.8(3) . .
O2 C4 C5 116.8(3) . .
C3 C4 C5 121.4(3) . .
C30 O5 Pr1 126.8(2) . .
C6 C5 C14 119.3(3) . .
C6 C5 C4 117.3(3) . .
C14 C5 C4 123.1(3) . .
C32 O6 Pr1 132.9(2) . .
C5 C6 C7 121.4(3) . .
C5 C6 H6 119.3 . .
C7 C6 H6 119.3 . .
C8 C9 C10 120.1(3) . .
C8 C9 H9 119.9 . .
C10 C9 H9 119.9 . .
C9 C8 C7 120.5(3) . .
C9 C8 H8 119.7 . .
C7 C8 H8 119.7 . .
C6 C7 C8 121.8(3) . .
C6 C7 C12 118.7(3) . .
C8 C7 C12 119.4(3) . .
C10 C11 C12 120.5(3) . .
C10 C11 H11 119.7 . .
C12 C11 H11 119.7 . .
C11 C10 C9 120.8(3) . .
C11 C10 H10 119.6 . .
C9 C10 H10 119.6 . .
C13 C12 C7 119.1(3) . .
C13 C12 C11 122.3(3) . .
C7 C12 C11 118.6(3) . .
C14 C13 C12 121.1(3) . .
C14 C13 H13 119.5 . .
C12 C13 H13 119.5 . .
F5 C15 F4 107.8(3) . .
F5 C15 F6 106.0(3) . .
F4 C15 F6 106.5(3) . .
F5 C15 C16 114.3(3) . .
F4 C15 C16 110.7(3) . .
F6 C15 C16 111.1(3) . .
C13 C14 C5 120.3(3) . .
C13 C14 H14 119.8 . .
C5 C14 H14 119.8 . .
O3 C16 C17 129.8(3) . .
O3 C16 C15 112.9(3) . .
C17 C16 C15 117.3(3) . .
C16 C17 C18 121.9(3) . .
C16 C17 H17 119.0 . .
C18 C17 H17 119.0 . .
C20 C19 C28 119.2(3) . .
C20 C19 C18 118.0(3) . .
C28 C19 C18 122.7(3) . .
O4 C18 C17 122.7(3) . .
O4 C18 C19 117.2(3) . .
C17 C18 C19 120.1(3) . .
C19 C20 C21 121.3(3) . .
C19 C20 H20 119.3 . .
C21 C20 H20 119.3 . .
C20 C21 C22 121.9(3) . .
C20 C21 C26 118.7(3) . .
C22 C21 C26 119.3(3) . .
C23 C22 C21 120.4(3) . .
C23 C22 H22 119.8 . .
C21 C22 H22 119.8 . .
C22 C23 C24 120.3(3) . .
C22 C23 H23 119.9 . .
C24 C23 H23 119.9 . .
C25 C24 C23 120.7(3) . .
C25 C24 H24 119.7 . .
C23 C24 H24 119.7 . .
C24 C25 C26 120.7(3) . .
C24 C25 H25 119.7 . .
C26 C25 H25 119.7 . .
C27 C26 C25 122.6(3) . .
C27 C26 C21 118.7(3) . .
C25 C26 C21 118.6(3) . .
C28 C27 C26 121.4(3) . .
C28 C27 H27 119.3 . .
C26 C27 H27 119.3 . .
C27 C28 C19 120.5(3) . .
C27 C28 H28 119.7 . .
C19 C28 H28 119.7 . .
F9 C29 F8 107.0(3) . .
F9 C29 F7 107.2(4) . .
F8 C29 F7 105.0(3) . .
F9 C29 C30 115.3(3) . .
F8 C29 C30 110.5(3) . .
F7 C29 C30 111.2(3) . .
O5 C30 C31 129.1(3) . .
O5 C30 C29 112.5(3) . .
C31 C30 C29 118.4(3) . .
C30 C31 C32 122.4(3) . .
C30 C31 H31 118.8 . .
C32 C31 H31 118.8 . .
O6 C32 C31 122.1(3) . .
O6 C32 C33 116.8(3) . .
C31 C32 C33 121.1(3) . .
C34 C33 C42 118.8(3) . .
C34 C33 C32 118.3(3) . .
C42 C33 C32 122.9(3) . .
C33 C34 C35 121.9(3) . .
C33 C34 H34 119.1 . .
C35 C34 H34 119.1 . .
C34 C35 C40 119.0(3) . .
C34 C35 C36 122.3(3) . .
C40 C35 C36 118.7(3) . .
C37 C36 C35 120.5(3) . .
C37 C36 H36 119.7 . .
C35 C36 H36 119.7 . .
C36 C37 C38 120.4(3) . .
C36 C37 H37 119.8 . .
C38 C37 H37 119.8 . .
C39 C38 C37 120.4(3) . .
C39 C38 H38 119.8 . .
C37 C38 H38 119.8 . .
C38 C39 C40 121.1(3) . .
C38 C39 H39 119.4 . .
C40 C39 H39 119.4 . .
C39 C40 C35 118.8(3) . .
C39 C40 C41 122.6(3) . .
C35 C40 C41 118.5(3) . .
C42 C41 C40 121.1(3) . .
C42 C41 H41 119.4 . .
C40 C41 H41 119.4 . .
C41 C42 C33 120.7(3) . .
C41 C42 H42 119.7 . .
C33 C42 H42 119.7 . .
N1 C43 C44 121.0(3) . .
N1 C43 C49 116.1(3) . .
C44 C43 C49 122.9(3) . .
C45 C44 C43 119.1(3) . .
C45 C44 H44 120.5 . .
C43 C44 H44 120.5 . .
C44 C45 C46 120.7(3) . .
C44 C45 H45 119.7 . .
C46 C45 H45 119.7 . .
C45 C46 C47 116.3(3) . .
C45 C46 C48 123.1(3) . .
C47 C46 C48 120.6(3) . .
N1 C47 C46 124.2(3) . .
N1 C47 H47 117.9 . .
C46 C47 H47 117.9 . .
C46 C48 H48A 109.5 . .
C46 C48 H48B 109.5 . .
H48A C48 H48B 109.5 . .
C46 C48 H48C 109.5 . .
H48A C48 H48C 109.5 . .
H48B C48 H48C 109.5 . .
N2 C49 C50 121.1(3) . .
N2 C49 C43 116.3(3) . .
C50 C49 C43 122.5(3) . .
C51 C50 C49 119.5(4) . .
C51 C50 H50 120.3 . .
C49 C50 H50 120.3 . .
C50 C51 C52 120.4(3) . .
C50 C51 H51 119.8 . .
C52 C51 H51 119.8 . .
C51 C52 C53 116.5(3) . .
C51 C52 C54 123.3(3) . .
C53 C52 C54 120.2(4) . .
N2 C53 C52 124.1(3) . .
N2 C53 H53 117.9 . .
C52 C53 H53 117.9 . .
C52 C54 H54A 109.5 . .
C52 C54 H54B 109.5 . .
H54A C54 H54B 109.5 . .
C52 C54 H54C 109.5 . .
H54A C54 H54C 109.5 . .
H54B C54 H54C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Pr1 O2 2.392(2) .
Pr1 O6 2.410(2) .
Pr1 O4 2.416(2) .
Pr1 O3 2.425(2) .
Pr1 O5 2.426(2) .
Pr1 O1 2.436(2) .
Pr1 N1 2.630(3) .
Pr1 N2 2.632(3) .
N1 C47 1.331(4) .
N1 C43 1.354(4) .
C1 F1 1.326(4) .
C1 F2 1.332(4) .
C1 F3 1.344(4) .
C1 C2 1.536(4) .
O1 C2 1.250(4) .
N2 C53 1.342(4) .
N2 C49 1.345(4) .
C2 C3 1.388(4) .
O2 C4 1.260(4) .
O3 C16 1.274(4) .
C3 C4 1.418(4) .
C3 H3 0.9500 .
O4 C18 1.255(4) .
C4 C5 1.485(4) .
F4 C15 1.327(4) .
O5 C30 1.264(4) .
F5 C15 1.323(4) .
C5 C6 1.385(4) .
C5 C14 1.419(4) .
O6 C32 1.267(4) .
C6 C7 1.410(4) .
C6 H6 0.9500 .
F6 C15 1.345(5) .
F9 C29 1.300(5) .
C9 C8 1.370(5) .
C9 C10 1.412(5) .
C9 H9 0.9500 .
F8 C29 1.334(4) .
C8 C7 1.417(5) .
C8 H8 0.9500 .
F7 C29 1.335(5) .
C7 C12 1.422(4) .
C11 C10 1.365(5) .
C11 C12 1.423(5) .
C11 H11 0.9500 .
C10 H10 0.9500 .
C12 C13 1.415(5) .
C13 C14 1.370(4) .
C13 H13 0.9500 .
C15 C16 1.535(5) .
C14 H14 0.9500 .
C16 C17 1.370(5) .
C17 C18 1.431(5) .
C17 H17 0.9500 .
C19 C20 1.375(5) .
C19 C28 1.417(4) .
C19 C18 1.495(4) .
C20 C21 1.416(5) .
C20 H20 0.9500 .
C21 C22 1.420(5) .
C21 C26 1.422(5) .
C22 C23 1.367(5) .
C22 H22 0.9500 .
C23 C24 1.411(5) .
C23 H23 0.9500 .
C24 C25 1.364(5) .
C24 H24 0.9500 .
C25 C26 1.420(5) .
C25 H25 0.9500 .
C26 C27 1.411(5) .
C27 C28 1.361(5) .
C27 H27 0.9500 .
C28 H28 0.9500 .
C29 C30 1.536(5) .
C30 C31 1.385(5) .
C31 C32 1.421(5) .
C31 H31 0.9500 .
C32 C33 1.491(4) .
C33 C34 1.375(6) .
C33 C42 1.426(4) .
C34 C35 1.410(4) .
C34 H34 0.9500 .
C35 C40 1.421(4) .
C35 C36 1.422(4) .
C36 C37 1.373(5) .
C36 H36 0.9500 .
C37 C38 1.406(5) .
C37 H37 0.9500 .
C38 C39 1.358(5) .
C38 H38 0.9500 .
C39 C40 1.418(5) .
C39 H39 0.9500 .
C40 C41 1.423(5) .
C41 C42 1.362(5) .
C41 H41 0.9500 .
C42 H42 0.9500 .
C43 C44 1.396(5) .
C43 C49 1.491(5) .
C44 C45 1.371(5) .
C44 H44 0.9500 .
C45 C46 1.389(5) .
C45 H45 0.9500 .
C46 C47 1.393(5) .
C46 C48 1.507(5) .
C47 H47 0.9500 .
C48 H48A 0.9800 .
C48 H48B 0.9800 .
C48 H48C 0.9800 .
C49 C50 1.392(5) .
C50 C51 1.379(6) .
C50 H50 0.9500 .
C51 C52 1.383(6) .
C51 H51 0.9500 .
C52 C53 1.394(5) .
C52 C54 1.508(5) .
C53 H53 0.9500 .
C54 H54A 0.9800 .
C54 H54B 0.9800 .
C54 H54C 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
Pr1 O1 C2 C3 22.3(5) . . . .
Pr1 O1 C2 C1 -159.4(2) . . . .
F1 C1 C2 O1 39.0(4) . . . .
F2 C1 C2 O1 -80.2(4) . . . .
F3 C1 C2 O1 160.1(3) . . . .
F1 C1 C2 C3 -142.5(3) . . . .
F2 C1 C2 C3 98.3(3) . . . .
F3 C1 C2 C3 -21.4(4) . . . .
O1 C2 C3 C4 -3.2(6) . . . .
C1 C2 C3 C4 178.5(3) . . . .
Pr1 O2 C4 C3 2.2(5) . . . .
Pr1 O2 C4 C5 -177.1(2) . . . .
C2 C3 C4 O2 -9.0(5) . . . .
C2 C3 C4 C5 170.2(3) . . . .
O2 C4 C5 C6 -11.4(4) . . . .
C3 C4 C5 C6 169.4(3) . . . .
O2 C4 C5 C14 162.3(3) . . . .
C3 C4 C5 C14 -16.9(5) . . . .
C14 C5 C6 C7 -2.8(5) . . . .
C4 C5 C6 C7 171.1(3) . . . .
C10 C9 C8 C7 0.8(5) . . . .
C5 C6 C7 C8 -175.8(3) . . . .
C5 C6 C7 C12 1.5(5) . . . .
C9 C8 C7 C6 176.4(3) . . . .
C9 C8 C7 C12 -0.9(5) . . . .
C12 C11 C10 C9 -0.7(5) . . . .
C8 C9 C10 C11 0.0(6) . . . .
C6 C7 C12 C13 1.3(5) . . . .
C8 C7 C12 C13 178.7(3) . . . .
C6 C7 C12 C11 -177.2(3) . . . .
C8 C7 C12 C11 0.2(5) . . . .
C10 C11 C12 C13 -177.9(3) . . . .
C10 C11 C12 C7 0.6(5) . . . .
C7 C12 C13 C14 -2.9(5) . . . .
C11 C12 C13 C14 175.6(3) . . . .
C12 C13 C14 C5 1.6(5) . . . .
C6 C5 C14 C13 1.3(5) . . . .
C4 C5 C14 C13 -172.3(3) . . . .
Pr1 O3 C16 C17 -20.9(5) . . . .
Pr1 O3 C16 C15 158.9(2) . . . .
F5 C15 C16 O3 173.3(3) . . . .
F4 C15 C16 O3 -64.7(4) . . . .
F6 C15 C16 O3 53.4(4) . . . .
F5 C15 C16 C17 -6.9(5) . . . .
F4 C15 C16 C17 115.1(4) . . . .
F6 C15 C16 C17 -126.8(3) . . . .
O3 C16 C17 C18 1.7(6) . . . .
C15 C16 C17 C18 -178.1(3) . . . .
Pr1 O4 C18 C17 3.2(5) . . . .
Pr1 O4 C18 C19 -176.9(2) . . . .
C16 C17 C18 O4 7.5(5) . . . .
C16 C17 C18 C19 -172.3(3) . . . .
C20 C19 C18 O4 13.2(4) . . . .
C28 C19 C18 O4 -164.4(3) . . . .
C20 C19 C18 C17 -166.9(3) . . . .
C28 C19 C18 C17 15.5(5) . . . .
C28 C19 C20 C21 0.8(5) . . . .
C18 C19 C20 C21 -176.8(3) . . . .
C19 C20 C21 C22 177.2(3) . . . .
C19 C20 C21 C26 0.5(5) . . . .
C20 C21 C22 C23 -174.4(3) . . . .
C26 C21 C22 C23 2.3(5) . . . .
C21 C22 C23 C24 -1.3(5) . . . .
C22 C23 C24 C25 -1.0(5) . . . .
C23 C24 C25 C26 2.2(5) . . . .
C24 C25 C26 C27 176.3(3) . . . .
C24 C25 C26 C21 -1.2(5) . . . .
C20 C21 C26 C27 -1.8(5) . . . .
C22 C21 C26 C27 -178.6(3) . . . .
C20 C21 C26 C25 175.7(3) . . . .
C22 C21 C26 C25 -1.0(5) . . . .
C25 C26 C27 C28 -175.7(3) . . . .
C21 C26 C27 C28 1.8(5) . . . .
C26 C27 C28 C19 -0.4(6) . . . .
C20 C19 C28 C27 -0.9(5) . . . .
C18 C19 C28 C27 176.7(3) . . . .
Pr1 O5 C30 C31 -32.3(5) . . . .
Pr1 O5 C30 C29 148.4(2) . . . .
F9 C29 C30 O5 179.3(4) . . . .
F8 C29 C30 O5 -59.2(4) . . . .
F7 C29 C30 O5 57.0(4) . . . .
F9 C29 C30 C31 0.0(5) . . . .
F8 C29 C30 C31 121.4(4) . . . .
F7 C29 C30 C31 -122.4(4) . . . .
O5 C30 C31 C32 -0.4(6) . . . .
C29 C30 C31 C32 178.9(3) . . . .
Pr1 O6 C32 C31 30.1(5) . . . .
Pr1 O6 C32 C33 -149.8(2) . . . .
C30 C31 C32 O6 3.0(5) . . . .
C30 C31 C32 C33 -177.1(3) . . . .
O6 C32 C33 C34 4.0(4) . . . .
C31 C32 C33 C34 -175.8(3) . . . .
O6 C32 C33 C42 -176.4(3) . . . .
C31 C32 C33 C42 3.7(5) . . . .
C42 C33 C34 C35 1.2(5) . . . .
C32 C33 C34 C35 -179.2(3) . . . .
C33 C34 C35 C40 0.3(5) . . . .
C33 C34 C35 C36 -179.8(3) . . . .
C34 C35 C36 C37 -178.9(3) . . . .
C40 C35 C36 C37 1.0(5) . . . .
C35 C36 C37 C38 -0.2(5) . . . .
C36 C37 C38 C39 -0.4(6) . . . .
C37 C38 C39 C40 0.1(5) . . . .
C38 C39 C40 C35 0.7(5) . . . .
C38 C39 C40 C41 -179.4(3) . . . .
C34 C35 C40 C39 178.7(3) . . . .
C36 C35 C40 C39 -1.2(5) . . . .
C34 C35 C40 C41 -1.3(5) . . . .
C36 C35 C40 C41 178.8(3) . . . .
C39 C40 C41 C42 -179.1(3) . . . .
C35 C40 C41 C42 0.8(5) . . . .
C40 C41 C42 C33 0.7(5) . . . .
C34 C33 C42 C41 -1.7(5) . . . .
C32 C33 C42 C41 178.7(3) . . . .
C47 N1 C43 C44 3.9(4) . . . .
Pr1 N1 C43 C44 -154.9(2) . . . .
C47 N1 C43 C49 -174.8(3) . . . .
Pr1 N1 C43 C49 26.3(3) . . . .
N1 C43 C44 C45 -3.0(5) . . . .
C49 C43 C44 C45 175.7(3) . . . .
C43 C44 C45 C46 -1.4(5) . . . .
C44 C45 C46 C47 4.6(5) . . . .
C44 C45 C46 C48 -174.4(3) . . . .
C43 N1 C47 C46 -0.4(5) . . . .
Pr1 N1 C47 C46 158.5(3) . . . .
C45 C46 C47 N1 -3.8(5) . . . .
C48 C46 C47 N1 175.2(3) . . . .
C53 N2 C49 C50 1.1(5) . . . .
Pr1 N2 C49 C50 179.5(2) . . . .
C53 N2 C49 C43 179.1(3) . . . .
Pr1 N2 C49 C43 -2.5(4) . . . .
N1 C43 C49 N2 -15.6(4) . . . .
C44 C43 C49 N2 165.6(3) . . . .
N1 C43 C49 C50 162.3(3) . . . .
C44 C43 C49 C50 -16.4(5) . . . .
N2 C49 C50 C51 -0.8(5) . . . .
C43 C49 C50 C51 -178.7(3) . . . .
C49 C50 C51 C52 -0.3(6) . . . .
C50 C51 C52 C53 1.0(6) . . . .
C50 C51 C52 C54 -179.9(4) . . . .
C49 N2 C53 C52 -0.3(5) . . . .
Pr1 N2 C53 C52 -178.7(3) . . . .
C51 C52 C53 N2 -0.8(5) . . . .
C54 C52 C53 N2 -179.9(4) . . . .
