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#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/82/1558290.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_1558290
loop_
_publ_author_name
'Hasegawa, Miki'
'Sakurai, Shoya'
'Yamaguchi, Masafumi Andrew'
'Iwasawa, Daichi'
'Yajima, Naho'
'Ogata, Shuhei'
'Inazuka, Yudai'
'Ishii, Ayumi'
'Suzuki, Kengo'
_publ_section_title
;
 Aspects of lanthanide complexes for selectivity, intensity and sharpness
 in luminescence bands from twenty-four praseodymium, europium and
 gadolinium complexes with differently distorted-hexadentate ligands.
;
_journal_issue                   8
_journal_name_full
'Photochemical & photobiological sciences : Official journal of the European Photochemistry Association and the European Society for Photobiology'
_journal_page_first              1054
_journal_page_last               1062
_journal_paper_doi               10.1039/d0pp00069h
_journal_volume                  19
_journal_year                    2020
_chemical_formula_sum            'C27 H25 F6 N9 O6 P Pr'
_chemical_formula_weight         857.44
_chemical_name_systematic        PrL2
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_block_doi                 10.5517/cc140wqr
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2015-01-14 deposited with the CCDC.	2020-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 119.0850(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.6944(13)
_cell_length_b                   12.1525(7)
_cell_length_c                   24.3587(18)
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.37
_cell_volume                     6388.2(7)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      90
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            35392
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         1.887
_exptl_absorpt_coefficient_mu    1.668
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
SADABS Sheldrick 1996 
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3408
_exptl_crystal_preparation       Luminescent
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_transmission_factor_max   1.80
_exptl_transmission_factor_min   1.57
_refine_diff_density_max         2.003
_refine_diff_density_min         -1.202
_refine_diff_density_rms         0.091
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     453
_refine_ls_number_reflns         7308
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.229
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0344
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0121P)²+42.2012P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0751
_refine_ls_wR_factor_ref         0.0758
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7032
_reflns_number_total             7308
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0pp00069h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1558290--1558295.cif.'
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               1558290
_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   0.555
_shelx_estimated_absorpt_t_max   0.635
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_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 0.81682(2) 0.50873(2) 0.12074(2) 0.01777(5) Uani 1 1 d . . . . .
P1 P 0.58592(4) 0.38862(7) 0.17296(4) 0.02559(19) Uani 1 1 d . . . . .
O1 O 0.89935(11) 0.5141(2) 0.23722(11) 0.0270(5) Uani 1 1 d . . . . .
O2 O 0.80616(11) 0.55386(19) 0.21752(11) 0.0233(5) Uani 1 1 d . . . . .
O3 O 0.87735(13) 0.5170(2) 0.31341(11) 0.0325(6) Uani 1 1 d . . . . .
O4 O 0.77006(11) 0.5666(2) 0.00438(11) 0.0267(5) Uani 1 1 d . . . . .
O5 O 0.80490(11) 0.3989(2) 0.02638(11) 0.0250(5) Uani 1 1 d . . . . .
O6 O 0.75147(15) 0.4507(3) -0.07134(12) 0.0414(7) Uani 1 1 d . . . . .
F1 F 0.58916(12) 0.51390(18) 0.15356(11) 0.0433(6) Uani 1 1 d . . . . .
F2 F 0.65554(9) 0.39677(19) 0.22929(10) 0.0342(5) Uani 1 1 d . . . . .
F3 F 0.61035(13) 0.3444(2) 0.12772(11) 0.0456(6) Uani 1 1 d . . . . .
F4 F 0.58180(12) 0.26583(18) 0.19360(12) 0.0446(6) Uani 1 1 d . . . . .
F5 F 0.51617(12) 0.3814(2) 0.11777(15) 0.0657(9) Uani 1 1 d . . . . .
F6 F 0.56242(12) 0.4347(2) 0.21993(14) 0.0475(6) Uani 1 1 d . . . . .
N1 N 0.80203(12) 0.3222(2) 0.16790(12) 0.0199(5) Uani 1 1 d . . . . .
N2 N 0.90186(12) 0.3512(3) 0.15306(13) 0.0253(6) Uani 1 1 d . . . . .
N3 N 0.91917(16) 0.5560(3) 0.12074(17) 0.0387(8) Uani 1 1 d . . . . .
N4 N 0.85219(16) 0.7137(3) 0.14012(16) 0.0343(7) Uani 1 1 d . . . . .
N5 N 0.73266(13) 0.6610(2) 0.10054(13) 0.0210(5) Uani 1 1 d . . . . .
N6 N 0.69720(12) 0.4544(2) 0.05793(12) 0.0178(5) Uani 1 1 d . . . . .
N7 N 0.86144(13) 0.5288(2) 0.25781(13) 0.0221(6) Uani 1 1 d . . . . .
N8 N 0.77468(13) 0.4722(2) -0.01532(13) 0.0253(6) Uani 1 1 d . . . . .
N9 N 0.49333(18) 0.1425(3) -0.0356(2) 0.0517(10) Uani 1 1 d . . . . .
C1 C 0.75600(15) 0.3141(3) 0.18200(15) 0.0221(6) Uani 1 1 d . . . . .
H1 H 0.7288 0.3750 0.1727 0.027 Uiso 1 1 calc R U . . .
C2 C 0.74568(16) 0.2222(3) 0.20936(15) 0.0233(7) Uani 1 1 d . . . . .
H2 H 0.7123 0.2200 0.2183 0.028 Uiso 1 1 calc R U . . .
C3 C 0.78559(18) 0.1340(3) 0.22321(16) 0.0290(8) Uani 1 1 d . . . . .
H3 H 0.7801 0.0698 0.2422 0.035 Uiso 1 1 calc R U . . .
C4 C 0.83336(17) 0.1397(3) 0.20927(16) 0.0288(8) Uani 1 1 d . . . . .
H4 H 0.8609 0.0794 0.2184 0.035 Uiso 1 1 calc R U . . .
C5 C 0.84073(15) 0.2353(3) 0.18157(15) 0.0230(7) Uani 1 1 d . . . . .
C6 C 0.89352(16) 0.2501(3) 0.16891(15) 0.0263(7) Uani 1 1 d . . . . .
C7 C 0.9343(2) 0.1634(4) 0.17660(17) 0.0396(10) Uani 1 1 d . . . . .
H7 H 0.9259 0.0908 0.1848 0.048 Uiso 1 1 calc R U . . .
C8 C 0.9867(2) 0.1855(5) 0.17209(18) 0.0488(13) Uani 1 1 d . . . . .
H8 H 1.0152 0.1284 0.1775 0.059 Uiso 1 1 calc R U . . .
C9 C 0.99730(17) 0.2907(5) 0.15975(18) 0.0446(12) Uani 1 1 d . . . . .
H9 H 1.0340 0.3081 0.1582 0.054 Uiso 1 1 calc R U . . .
C10 C 0.95346(16) 0.3723(4) 0.14942(16) 0.0341(9) Uani 1 1 d . . . . .
C11 C 0.96207(18) 0.4856(4) 0.1352(2) 0.0423(11) Uani 1 1 d . . . . .
H11 H 0.9999 0.5067 0.1369 0.051 Uiso 1 1 calc R U . . .
C12 C 0.9344(3) 0.6694(4) 0.1164(2) 0.0624(16) Uani 1 1 d D . . . .
H12 H 0.9801 0.6756 0.1329 0.075 Uiso 1 1 calc R U . . .
C13 C 0.9163(2) 0.7412(4) 0.1555(3) 0.0628(16) Uani 1 1 d . . . . .
H13A H 0.9449 0.7284 0.2007 0.075 Uiso 1 1 calc R U . . .
H13B H 0.9190 0.8197 0.1462 0.075 Uiso 1 1 calc R U . . .
C14 C 0.8169(2) 0.7878(3) 0.14115(18) 0.0339(9) Uani 1 1 d . . . . .
H14 H 0.8317 0.8611 0.1518 0.041 Uiso 1 1 calc R U . . .
C15 C 0.75311(17) 0.7613(3) 0.12601(16) 0.0259(7) Uani 1 1 d . . . . .
C16 C 0.71698(19) 0.8353(3) 0.13684(17) 0.0314(8) Uani 1 1 d . . . . .
H16 H 0.7327 0.9057 0.1543 0.038 Uiso 1 1 calc R U . . .
C17 C 0.65753(19) 0.8050(3) 0.12184(18) 0.0329(8) Uani 1 1 d . . . . .
H17 H 0.6322 0.8532 0.1303 0.040 Uiso 1 1 calc R U . . .
C18 C 0.63524(18) 0.7032(3) 0.09420(17) 0.0287(7) Uani 1 1 d . . . . .
H18 H 0.5942 0.6811 0.0829 0.034 Uiso 1 1 calc R U . . .
C19 C 0.67404(16) 0.6339(3) 0.08323(15) 0.0210(6) Uani 1 1 d . . . . .
C20 C 0.65243(15) 0.5267(3) 0.05015(15) 0.0197(6) Uani 1 1 d . . . . .
C21 C 0.59001(15) 0.5044(3) 0.01098(16) 0.0248(7) Uani 1 1 d . . . . .
H21 H 0.5594 0.5564 0.0065 0.030 Uiso 1 1 calc R U . . .
C22 C 0.57302(15) 0.4061(3) -0.02126(16) 0.0256(7) Uani 1 1 d . . . . .
H22 H 0.5306 0.3896 -0.0484 0.031 Uiso 1 1 calc R U . . .
C23 C 0.61886(15) 0.3315(3) -0.01348(15) 0.0218(6) Uani 1 1 d . . . . .
H23 H 0.6084 0.2635 -0.0355 0.026 Uiso 1 1 calc R U . . .
C24 C 0.67988(15) 0.3584(3) 0.02701(15) 0.0198(6) Uani 1 1 d . . . . .
H24 H 0.7111 0.3064 0.0333 0.024 Uiso 1 1 calc R U . . .
C25 C 0.9022(3) 0.7020(5) 0.0503(3) 0.0765(18) Uani 1 1 d D . . . .
H25A H 0.9188 0.6602 0.0274 0.115 Uiso 1 1 calc R U . . .
H25B H 0.9085 0.7808 0.0470 0.115 Uiso 1 1 calc R U . . .
H25C H 0.8578 0.6870 0.0323 0.115 Uiso 1 1 calc R U . . .
C26 C 0.6011(2) 0.0975(4) 0.05794(19) 0.0438(10) Uani 1 1 d . . . . .
H26A H 0.6009 0.0227 0.0729 0.066 Uiso 1 1 calc R U . . .
H26B H 0.6116 0.1500 0.0922 0.066 Uiso 1 1 calc R U . . .
H26C H 0.6320 0.1024 0.0438 0.066 Uiso 1 1 calc R U . . .
C27 C 0.54037(19) 0.1234(3) 0.00612(18) 0.0320(8) Uani 1 1 d . . . . .
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'
P P 0.1023 0.0942 '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
_geom_angle_publ_flag
O5 Pr1 O2 157.81(8) . . ?
O5 Pr1 O1 133.79(8) . . ?
O2 Pr1 O1 50.00(7) . . ?
O5 Pr1 O4 50.14(8) . . ?
O2 Pr1 O4 139.63(8) . . ?
O1 Pr1 O4 153.74(8) . . ?
O5 Pr1 N3 78.53(9) . . ?
O2 Pr1 N3 119.35(9) . . ?
O1 Pr1 N3 75.17(10) . . ?
O4 Pr1 N3 81.69(10) . . ?
O5 Pr1 N4 123.07(9) . . ?
O2 Pr1 N4 78.67(9) . . ?
O1 Pr1 N4 76.07(10) . . ?
O4 Pr1 N4 82.55(9) . . ?
N3 Pr1 N4 63.07(11) . . ?
O5 Pr1 N5 117.58(8) . . ?
O2 Pr1 N5 66.26(8) . . ?
O1 Pr1 N5 108.53(8) . . ?
O4 Pr1 N5 73.37(8) . . ?
N3 Pr1 N5 121.55(11) . . ?
N4 Pr1 N5 61.88(10) . . ?
O5 Pr1 N1 87.89(8) . . ?
O2 Pr1 N1 71.66(8) . . ?
O1 Pr1 N1 75.22(8) . . ?
O4 Pr1 N1 128.82(8) . . ?
N3 Pr1 N1 122.03(11) . . ?
N4 Pr1 N1 147.70(9) . . ?
N5 Pr1 N1 114.74(8) . . ?
O5 Pr1 N2 67.58(8) . . ?
O2 Pr1 N2 107.56(8) . . ?
O1 Pr1 N2 66.62(8) . . ?
O4 Pr1 N2 112.80(8) . . ?
N3 Pr1 N2 61.99(11) . . ?
N4 Pr1 N2 119.15(10) . . ?
N5 Pr1 N2 173.70(8) . . ?
N1 Pr1 N2 60.73(9) . . ?
O5 Pr1 N6 75.08(8) . . ?
O2 Pr1 N6 90.02(8) . . ?
O1 Pr1 N6 134.72(8) . . ?
O4 Pr1 N6 70.02(8) . . ?
N3 Pr1 N6 149.68(10) . . ?
N4 Pr1 N6 121.41(10) . . ?
N5 Pr1 N6 61.01(8) . . ?
N1 Pr1 N6 71.86(8) . . ?
N2 Pr1 N6 119.08(8) . . ?
O5 Pr1 N7 150.80(8) . . ?
O2 Pr1 N7 25.16(7) . . ?
O1 Pr1 N7 25.17(7) . . ?
O4 Pr1 N7 158.93(8) . . ?
N3 Pr1 N7 98.78(10) . . ?
N4 Pr1 N7 79.02(9) . . ?
N5 Pr1 N7 88.87(8) . . ?
N1 Pr1 N7 68.70(8) . . ?
N2 Pr1 N7 85.32(8) . . ?
N6 Pr1 N7 111.54(8) . . ?
O5 Pr1 N8 25.27(8) . . ?
O2 Pr1 N8 156.85(8) . . ?
O1 Pr1 N8 153.14(8) . . ?
O4 Pr1 N8 25.04(8) . . ?
N3 Pr1 N8 81.17(9) . . ?
N4 Pr1 N8 104.38(9) . . ?
N5 Pr1 N8 94.53(8) . . ?
N1 Pr1 N8 107.92(8) . . ?
N2 Pr1 N8 91.18(8) . . ?
N6 Pr1 N8 68.59(8) . . ?
N7 Pr1 N8 176.03(8) . . ?
F3 P1 F5 90.88(17) . . ?
F3 P1 F4 90.37(15) . . ?
F5 P1 F4 90.35(14) . . ?
F3 P1 F2 90.21(13) . . ?
F5 P1 F2 178.92(18) . . ?
F4 P1 F2 89.66(13) . . ?
F3 P1 F1 91.49(14) . . ?
F5 P1 F1 89.54(14) . . ?
F4 P1 F1 178.14(16) . . ?
F2 P1 F1 90.41(13) . . ?
F3 P1 F6 178.82(15) . . ?
F5 P1 F6 90.21(17) . . ?
F4 P1 F6 90.08(15) . . ?
F2 P1 F6 88.71(13) . . ?
F1 P1 F6 88.06(14) . . ?
N7 O1 Pr1 95.64(18) . . ?
N7 O2 Pr1 96.15(17) . . ?
N8 O4 Pr1 95.44(18) . . ?
N8 O5 Pr1 96.77(18) . . ?
C1 N1 C5 117.7(3) . . ?
C1 N1 Pr1 119.2(2) . . ?
C5 N1 Pr1 123.1(2) . . ?
C6 N2 C10 118.6(3) . . ?
C6 N2 Pr1 122.5(2) . . ?
C10 N2 Pr1 118.7(3) . . ?
C11 N3 C12 116.8(4) . . ?
C11 N3 Pr1 122.1(3) . . ?
C12 N3 Pr1 120.0(3) . . ?
C14 N4 C13 120.0(3) . . ?
C14 N4 Pr1 120.8(2) . . ?
C13 N4 Pr1 119.0(3) . . ?
C19 N5 C15 118.2(3) . . ?
C19 N5 Pr1 121.3(2) . . ?
C15 N5 Pr1 117.5(2) . . ?
C24 N6 C20 118.1(3) . . ?
C24 N6 Pr1 120.0(2) . . ?
C20 N6 Pr1 121.4(2) . . ?
O3 N7 O1 121.3(3) . . ?
O3 N7 O2 122.0(3) . . ?
O1 N7 O2 116.7(3) . . ?
O3 N7 Pr1 168.3(2) . . ?
O1 N7 Pr1 59.18(15) . . ?
O2 N7 Pr1 58.69(15) . . ?
O6 N8 O4 122.4(3) . . ?
O6 N8 O5 120.7(3) . . ?
O4 N8 O5 116.9(3) . . ?
O6 N8 Pr1 172.3(2) . . ?
O4 N8 Pr1 59.52(15) . . ?
O5 N8 Pr1 57.96(15) . . ?
N1 C1 C2 124.0(3) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 H2 121.1 . . ?
C1 C2 H2 121.1 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 116.1(3) . . ?
C4 C5 C6 122.2(3) . . ?
N2 C6 C7 121.8(4) . . ?
N2 C6 C5 116.4(3) . . ?
C7 C6 C5 121.6(4) . . ?
C8 C7 C6 118.9(4) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.1(4) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 119.3(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 121.9(4) . . ?
N2 C10 C11 116.6(3) . . ?
C9 C10 C11 121.5(4) . . ?
N3 C11 C10 120.2(3) . . ?
N3 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C25 C12 N3 108.5(4) . . ?
C25 C12 C13 111.6(6) . . ?
N3 C12 C13 109.7(4) . . ?
C25 C12 H12 109.0 . . ?
N3 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
N4 C13 C12 108.6(4) . . ?
N4 C13 H13A 110.0 . . ?
C12 C13 H13A 110.0 . . ?
N4 C13 H13B 110.0 . . ?
C12 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?
N4 C14 C15 120.4(3) . . ?
N4 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
N5 C15 C16 123.0(3) . . ?
N5 C15 C14 115.4(3) . . ?
C16 C15 C14 121.6(3) . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C17 C18 C19 118.9(4) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
N5 C19 C18 122.0(3) . . ?
N5 C19 C20 115.8(3) . . ?
C18 C19 C20 122.2(3) . . ?
N6 C20 C21 121.9(3) . . ?
N6 C20 C19 116.1(3) . . ?
C21 C20 C19 121.9(3) . . ?
C22 C21 C20 119.3(3) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C23 119.1(3) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 H22 120.5 . . ?
C24 C23 C22 118.5(3) . . ?
C24 C23 H23 120.8 . . ?
C22 C23 H23 120.8 . . ?
N6 C24 C23 123.2(3) . . ?
N6 C24 H24 118.4 . . ?
C23 C24 H24 118.4 . . ?
C12 C25 H25A 109.5 . . ?
C12 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C12 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C27 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N9 C27 C26 178.1(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
Pr1 O5 2.548(2) . ?
Pr1 O2 2.556(2) . ?
Pr1 O1 2.566(2) . ?
Pr1 O4 2.584(2) . ?
Pr1 N3 2.592(3) . ?
Pr1 N4 2.606(3) . ?
Pr1 N5 2.644(3) . ?
Pr1 N1 2.645(3) . ?
Pr1 N2 2.662(3) . ?
Pr1 N6 2.666(3) . ?
Pr1 N7 2.974(3) . ?
Pr1 N8 2.985(3) . ?
P1 F3 1.586(3) . ?
P1 F5 1.591(2) . ?
P1 F4 1.594(2) . ?
P1 F2 1.598(2) . ?
P1 F1 1.608(2) . ?
P1 F6 1.614(3) . ?
O1 N7 1.271(4) . ?
O2 N7 1.272(4) . ?
O3 N7 1.222(4) . ?
O4 N8 1.269(4) . ?
O5 N8 1.283(4) . ?
O6 N8 1.224(4) . ?
N1 C1 1.342(4) . ?
N1 C5 1.354(4) . ?
N2 C6 1.334(5) . ?
N2 C10 1.344(5) . ?
N3 C11 1.271(6) . ?
N3 C12 1.446(6) . ?
N4 C14 1.262(5) . ?
N4 C13 1.478(5) . ?
N5 C19 1.337(4) . ?
N5 C15 1.350(4) . ?
N6 C24 1.341(4) . ?
N6 C20 1.352(4) . ?
N9 C27 1.135(5) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(5) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.489(5) . ?
C6 C7 1.406(5) . ?
C7 C8 1.378(6) . ?
C7 H7 0.9500 . ?
C8 C9 1.367(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.398(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.460(7) . ?
C11 H11 0.9500 . ?
C12 C25 1.461(4) . ?
C12 C13 1.509(7) . ?
C12 H12 1.0000 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.468(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.379(5) . ?
C16 C17 1.379(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.396(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.487(4) . ?
C20 C21 1.389(5) . ?
C21 C22 1.378(5) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(4) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 C27 1.450(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
Pr1 O1 N7 O3 166.3(3) . . . . ?
Pr1 O1 N7 O2 -12.2(3) . . . . ?
Pr1 O2 N7 O3 -166.2(3) . . . . ?
Pr1 O2 N7 O1 12.2(3) . . . . ?
Pr1 O4 N8 O6 171.2(3) . . . . ?
Pr1 O4 N8 O5 -8.5(3) . . . . ?
Pr1 O5 N8 O6 -171.1(3) . . . . ?
Pr1 O5 N8 O4 8.6(3) . . . . ?
C5 N1 C1 C2 -0.3(5) . . . . ?
Pr1 N1 C1 C2 -177.1(2) . . . . ?
N1 C1 C2 C3 0.4(5) . . . . ?
C1 C2 C3 C4 -0.4(5) . . . . ?
C2 C3 C4 C5 0.3(5) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
Pr1 N1 C5 C4 176.9(2) . . . . ?
C1 N1 C5 C6 -176.3(3) . . . . ?
Pr1 N1 C5 C6 0.4(4) . . . . ?
C3 C4 C5 N1 -0.2(5) . . . . ?
C3 C4 C5 C6 176.1(3) . . . . ?
C10 N2 C6 C7 -5.5(5) . . . . ?
Pr1 N2 C6 C7 170.2(3) . . . . ?
C10 N2 C6 C5 171.2(3) . . . . ?
Pr1 N2 C6 C5 -13.2(4) . . . . ?
N1 C5 C6 N2 8.2(4) . . . . ?
C4 C5 C6 N2 -168.3(3) . . . . ?
N1 C5 C6 C7 -175.2(3) . . . . ?
C4 C5 C6 C7 8.4(5) . . . . ?
N2 C6 C7 C8 4.8(5) . . . . ?
C5 C6 C7 C8 -171.7(3) . . . . ?
C6 C7 C8 C9 -0.6(6) . . . . ?
C7 C8 C9 C10 -2.6(6) . . . . ?
C6 N2 C10 C9 2.1(5) . . . . ?
Pr1 N2 C10 C9 -173.7(3) . . . . ?
C6 N2 C10 C11 -176.8(3) . . . . ?
Pr1 N2 C10 C11 7.4(4) . . . . ?
C8 C9 C10 N2 2.0(6) . . . . ?
C8 C9 C10 C11 -179.2(4) . . . . ?
C12 N3 C11 C10 171.2(4) . . . . ?
Pr1 N3 C11 C10 3.3(5) . . . . ?
N2 C10 C11 N3 -7.2(5) . . . . ?
C9 C10 C11 N3 173.9(4) . . . . ?
C11 N3 C12 C25 109.3(5) . . . . ?
Pr1 N3 C12 C25 -82.5(5) . . . . ?
C11 N3 C12 C13 -128.6(5) . . . . ?
Pr1 N3 C12 C13 39.7(6) . . . . ?
C14 N4 C13 C12 -146.5(4) . . . . ?
Pr1 N4 C13 C12 38.8(6) . . . . ?
C25 C12 C13 N4 71.7(6) . . . . ?
N3 C12 C13 N4 -48.6(6) . . . . ?
C13 N4 C14 C15 -180.0(4) . . . . ?
Pr1 N4 C14 C15 -5.3(5) . . . . ?
C19 N5 C15 C16 2.2(5) . . . . ?
Pr1 N5 C15 C16 -158.5(3) . . . . ?
C19 N5 C15 C14 -177.2(3) . . . . ?
Pr1 N5 C15 C14 22.1(4) . . . . ?
N4 C14 C15 N5 -11.6(5) . . . . ?
N4 C14 C15 C16 168.9(4) . . . . ?
N5 C15 C16 C17 0.9(5) . . . . ?
C14 C15 C16 C17 -179.7(3) . . . . ?
C15 C16 C17 C18 -2.5(5) . . . . ?
C16 C17 C18 C19 0.9(5) . . . . ?
C15 N5 C19 C18 -3.9(5) . . . . ?
Pr1 N5 C19 C18 156.0(3) . . . . ?
C15 N5 C19 C20 174.6(3) . . . . ?
Pr1 N5 C19 C20 -25.5(4) . . . . ?
C17 C18 C19 N5 2.4(5) . . . . ?
C17 C18 C19 C20 -176.0(3) . . . . ?
C24 N6 C20 C21 -0.6(5) . . . . ?
Pr1 N6 C20 C21 171.7(2) . . . . ?
C24 N6 C20 C19 -177.5(3) . . . . ?
Pr1 N6 C20 C19 -5.2(4) . . . . ?
N5 C19 C20 N6 19.7(4) . . . . ?
C18 C19 C20 N6 -161.9(3) . . . . ?
N5 C19 C20 C21 -157.1(3) . . . . ?
C18 C19 C20 C21 21.3(5) . . . . ?
N6 C20 C21 C22 -0.4(5) . . . . ?
C19 C20 C21 C22 176.3(3) . . . . ?
C20 C21 C22 C23 0.3(5) . . . . ?
C21 C22 C23 C24 0.7(5) . . . . ?
C20 N6 C24 C23 1.8(5) . . . . ?
Pr1 N6 C24 C23 -170.6(2) . . . . ?
C22 C23 C24 N6 -1.9(5) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168306439
