# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences.
# This journal is © The Royal Society of Chemistry and Owner Societies 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_audit_block_doi                 10.5517/cc140wqr
_database_code_depnum_ccdc_archive 'CCDC 1043544'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        PrL2
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 F6 N9 O6 P Pr'
_chemical_formula_weight         857.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   24.6944(13)
_cell_length_b                   12.1525(7)
_cell_length_c                   24.3587(18)
_cell_angle_alpha                90
_cell_angle_beta                 119.0850(10)
_cell_angle_gamma                90
_cell_volume                     6388.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      27.50

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.783
_exptl_crystal_F_000             3408
_exptl_transmission_factor_min   1.57
_exptl_transmission_factor_max   1.80
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    1.668
_shelx_estimated_absorpt_T_min   0.555
_shelx_estimated_absorpt_T_max   0.635
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
SADABS Sheldrick 1996 
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            35392
_diffrn_reflns_av_unetI/netI     0.0150
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.887
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7308
_reflns_number_gt                7032
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0121P)²+42.2012P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7308
_refine_ls_number_parameters     453
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0758
_refine_ls_wR_factor_gt          0.0751
_refine_ls_goodness_of_fit_ref   1.224
_refine_ls_restrained_S_all      1.229
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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 . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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_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_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) . . . . ?

_refine_diff_density_max         2.003
_refine_diff_density_min         -1.202
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1861235'
loop_
_audit_author_name
_audit_author_address
'Shuhei Ogata, Miki Hasegawa'
;Aoyama Gakuin University
Japan
;
_audit_update_record             
;
2018-08-09 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 Eu N8 O6, F6 P, C2 H3 N'
_chemical_formula_sum            'C27 H25 Eu F6 N9 O6 P'
_chemical_formula_weight         868.49

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2647(9)
_cell_length_b                   11.7465(8)
_cell_length_c                   20.5653(14)
_cell_angle_alpha                90
_cell_angle_beta                 96.9060(10)
_cell_angle_gamma                90
_cell_volume                     3181.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    0
_cell_measurement_theta_min      0
_cell_measurement_theta_max      0

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             1720
_exptl_transmission_factor_min   1.68
_exptl_transmission_factor_max   1.97
_exptl_crystal_size_max          0.372
_exptl_crystal_size_mid          0.372
_exptl_crystal_size_min          0.272
_exptl_absorpt_coefficient_mu    2.115
_shelx_estimated_absorpt_T_min   0.507
_shelx_estimated_absorpt_T_max   0.597
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            35104
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_max         27.514
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7272
_reflns_number_gt                6967
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+3.7941P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7272
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0201
_refine_ls_R_factor_gt           0.0192
_refine_ls_wR_factor_ref         0.0497
_refine_ls_wR_factor_gt          0.0493
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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
Eu1 Eu 0.35686(2) 0.21863(2) 0.36802(2) 0.01221(3) Uani 1 1 d . . . . .
P1 P 0.26405(4) 0.06129(5) 0.72462(3) 0.02489(11) Uani 1 1 d . . . . .
O1 O 0.47595(10) 0.06724(11) 0.41618(7) 0.0177(3) Uani 1 1 d . . . . .
O2 O 0.37075(10) 0.01377(11) 0.33285(6) 0.0182(3) Uani 1 1 d . . . . .
O3 O 0.46196(11) -0.11314(12) 0.39144(7) 0.0235(3) Uani 1 1 d . . . . .
O4 O 0.36530(10) 0.43342(12) 0.35487(7) 0.0203(3) Uani 1 1 d . . . . .
O5 O 0.21736(10) 0.36673(11) 0.36907(7) 0.0193(3) Uani 1 1 d . . . . .
O6 O 0.23550(12) 0.54838(12) 0.35163(8) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.25660(12) 0.08810(13) 0.43903(8) 0.0162(3) Uani 1 1 d . . . . .
N2 N 0.17610(11) 0.15568(13) 0.31959(7) 0.0140(3) Uani 1 1 d . . . . .
N3 N 0.30034(13) 0.27474(13) 0.24889(8) 0.0165(3) Uani 1 1 d . . . . .
N4 N 0.50219(13) 0.21341(13) 0.29866(8) 0.0171(3) Uani 1 1 d . . . . .
N5 N 0.52888(12) 0.29450(13) 0.42274(8) 0.0149(3) Uani 1 1 d . . . . .
N6 N 0.36227(12) 0.30631(14) 0.48462(8) 0.0166(3) Uani 1 1 d . . . . .
N7 N 0.43755(12) -0.01406(13) 0.38031(8) 0.0166(3) Uani 1 1 d . . . . .
N8 N 0.27141(13) 0.45242(14) 0.35814(8) 0.0188(3) Uani 1 1 d . . . . .
N9 N 0.9990(2) 0.3111(3) 0.48452(14) 0.0548(7) Uani 1 1 d . . . . .
F1 F 0.15142(9) 0.07306(11) 0.74530(7) 0.0306(3) Uani 1 1 d . . . . .
F2 F 0.28868(11) -0.02914(14) 0.78376(7) 0.0380(3) Uani 1 1 d . . . . .
F3 F 0.37702(11) 0.04642(14) 0.70659(8) 0.0437(4) Uani 1 1 d . . . . .
F4 F 0.23783(16) 0.14724(17) 0.66680(10) 0.0668(6) Uani 1 1 d . . . . .
F5 F 0.22820(11) -0.04408(13) 0.67810(7) 0.0359(3) Uani 1 1 d . . . . .
F6 F 0.30144(12) 0.16167(15) 0.77427(9) 0.0517(5) Uani 1 1 d . . . . .
C1 C 0.30331(15) 0.04565(17) 0.49567(9) 0.0193(4) Uani 1 1 d . . . . .
H1 H 0.3703 0.0706 0.5104 0.023 Uiso 1 1 calc R U . . .
C2 C 0.25818(16) -0.03250(18) 0.53321(10) 0.0225(4) Uani 1 1 d . . . . .
H2 H 0.2934 -0.0606 0.5729 0.027 Uiso 1 1 calc R U . . .
C3 C 0.16076(17) -0.06905(18) 0.51178(10) 0.0243(4) Uani 1 1 d . . . . .
H3 H 0.1282 -0.1233 0.5364 0.029 Uiso 1 1 calc R U . . .
C4 C 0.11109(15) -0.02567(17) 0.45395(10) 0.0205(4) Uani 1 1 d . . . . .
H4 H 0.0441 -0.0496 0.4385 0.025 Uiso 1 1 calc R U . . .
C5 C 0.16101(14) 0.05369(15) 0.41882(9) 0.0155(3) Uani 1 1 d . . . . .
C6 C 0.11281(14) 0.10405(15) 0.35646(9) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.00818(14) 0.09982(17) 0.33738(10) 0.0189(4) Uani 1 1 d . . . . .
H7 H -0.0350 0.0613 0.3638 0.023 Uiso 1 1 calc R U . . .
C8 C -0.03208(14) 0.15214(17) 0.27972(10) 0.0207(4) Uani 1 1 d . . . . .
H8 H -0.1032 0.1515 0.2666 0.025 Uiso 1 1 calc R U . . .
C9 C 0.03290(15) 0.20551(16) 0.24135(10) 0.0190(4) Uani 1 1 d . . . . .
H9 H 0.0074 0.2419 0.2015 0.023 Uiso 1 1 calc R U . . .
C10 C 0.13619(14) 0.20433(15) 0.26272(9) 0.0157(3) Uani 1 1 d . . . . .
C11 C 0.20810(15) 0.26241(16) 0.22507(9) 0.0166(4) Uani 1 1 d . . . . .
H11 H 0.1855 0.2910 0.1826 0.020 Uiso 1 1 calc R U . . .
C12 C 0.36711(15) 0.33764(17) 0.20968(10) 0.0200(4) Uani 1 1 d . . . . .
H12A H 0.4036 0.3974 0.2371 0.024 Uiso 1 1 calc R U . . .
H12B H 0.3254 0.3756 0.1728 0.024 Uiso 1 1 calc R U . . .
C13 C 0.44446(16) 0.25945(19) 0.18274(10) 0.0220(4) Uani 1 1 d . . . . .
H13A H 0.5014 0.3062 0.1705 0.026 Uiso 1 1 calc R U . . .
H13B H 0.4118 0.2220 0.1425 0.026 Uiso 1 1 calc R U . . .
C14 C 0.48691(15) 0.16775(17) 0.23153(9) 0.0205(4) Uani 1 1 d . . . . .
H14A H 0.4391 0.1027 0.2296 0.025 Uiso 1 1 calc R U . . .
H14B H 0.5524 0.1396 0.2193 0.025 Uiso 1 1 calc R U . . .
C15 C 0.59253(15) 0.23743(16) 0.32332(10) 0.0181(4) Uani 1 1 d . . . . .
H15 H 0.6477 0.2261 0.2985 0.022 Uiso 1 1 calc R U . . .
C16 C 0.61096(15) 0.28280(15) 0.39042(10) 0.0173(4) Uani 1 1 d . . . . .
C17 C 0.70877(15) 0.30857(17) 0.41841(11) 0.0217(4) Uani 1 1 d . . . . .
H17 H 0.7647 0.3024 0.3938 0.026 Uiso 1 1 calc R U . . .
C18 C 0.72266(15) 0.34360(18) 0.48332(11) 0.0243(4) Uani 1 1 d . . . . .
H18 H 0.7888 0.3601 0.5042 0.029 Uiso 1 1 calc R U . . .
C19 C 0.63950(15) 0.35418(17) 0.51722(10) 0.0218(4) Uani 1 1 d . . . . .
H19 H 0.6478 0.3769 0.5619 0.026 Uiso 1 1 calc R U . . .
C20 C 0.54264(14) 0.33098(15) 0.48491(9) 0.0163(3) Uani 1 1 d . . . . .
C21 C 0.44956(14) 0.34500(15) 0.51779(9) 0.0163(3) Uani 1 1 d . . . . .
C22 C 0.45191(16) 0.39625(17) 0.57898(9) 0.0206(4) Uani 1 1 d . . . . .
H22 H 0.5140 0.4244 0.6009 0.025 Uiso 1 1 calc R U . . .
C23 C 0.36308(16) 0.40588(17) 0.60756(10) 0.0227(4) Uani 1 1 d . . . . .
H23 H 0.3635 0.4399 0.6495 0.027 Uiso 1 1 calc R U . . .
C24 C 0.27364(16) 0.36520(17) 0.57418(10) 0.0222(4) Uani 1 1 d . . . . .
H24 H 0.2116 0.3702 0.5928 0.027 Uiso 1 1 calc R U . . .
C25 C 0.27658(15) 0.31699(17) 0.51296(10) 0.0198(4) Uani 1 1 d . . . . .
H25 H 0.2149 0.2901 0.4898 0.024 Uiso 1 1 calc R U . . .
C26 C 0.9901(2) 0.4532(3) 0.38806(14) 0.0450(7) Uani 1 1 d . . . . .
H26A H 0.9402 0.4264 0.3523 0.067 Uiso 1 1 calc R U . . .
H26B H 1.0569 0.4591 0.3725 0.067 Uiso 1 1 calc R U . . .
H26C H 0.9696 0.5281 0.4028 0.067 Uiso 1 1 calc R U . . .
C27 C 0.99541(17) 0.3733(2) 0.44216(13) 0.0375(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Eu1 O1 2.5025(13) . ?
Eu1 O2 2.5258(13) . ?
Eu1 N4 2.5330(16) . ?
Eu1 O4 2.5414(14) . ?
Eu1 O5 2.5417(14) . ?
Eu1 N3 2.5606(16) . ?
Eu1 N5 2.5787(16) . ?
Eu1 N2 2.5910(15) . ?
Eu1 N1 2.5921(16) . ?
Eu1 N6 2.6028(16) . ?
Eu1 N7 2.9353(16) . ?
Eu1 N8 2.9685(16) . ?
P1 F4 1.5666(17) . ?
P1 F3 1.5959(15) . ?
P1 F6 1.5991(16) . ?
P1 F5 1.6012(15) . ?
P1 F1 1.6078(13) . ?
P1 F2 1.6184(15) . ?
O1 N7 1.275(2) . ?
O2 N7 1.279(2) . ?
O3 N7 1.222(2) . ?
O4 N8 1.275(2) . ?
O5 N8 1.271(2) . ?
O6 N8 1.225(2) . ?
N1 C5 1.348(2) . ?
N1 C1 1.348(2) . ?
N2 C6 1.342(2) . ?
N2 C10 1.351(2) . ?
N3 C11 1.270(3) . ?
N3 C12 1.467(2) . ?
N4 C15 1.276(3) . ?
N4 C14 1.472(2) . ?
N5 C20 1.340(2) . ?
N5 C16 1.349(3) . ?
N6 C25 1.344(3) . ?
N6 C21 1.350(2) . ?
N9 C27 1.133(4) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.383(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.485(3) . ?
C6 C7 1.397(3) . ?
C7 C8 1.384(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.467(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.530(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.532(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.472(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.388(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.401(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.486(3) . ?
C21 C22 1.392(3) . ?
C22 C23 1.383(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.382(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.451(4) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
O1 Eu1 O2 51.10(4) . . ?
O1 Eu1 N4 73.67(5) . . ?
O2 Eu1 N4 74.28(5) . . ?
O1 Eu1 O4 135.55(4) . . ?
O2 Eu1 O4 155.46(5) . . ?
N4 Eu1 O4 85.29(5) . . ?
O1 Eu1 O5 155.31(4) . . ?
O2 Eu1 O5 137.12(4) . . ?
N4 Eu1 O5 128.72(5) . . ?
O4 Eu1 O5 50.42(4) . . ?
O1 Eu1 N3 131.29(5) . . ?
O2 Eu1 N3 89.67(5) . . ?
N4 Eu1 N3 67.82(5) . . ?
O4 Eu1 N3 69.77(5) . . ?
O5 Eu1 N3 72.68(5) . . ?
O1 Eu1 N5 65.77(4) . . ?
O2 Eu1 N5 111.28(5) . . ?
N4 Eu1 N5 63.94(5) . . ?
O4 Eu1 N5 69.84(4) . . ?
O5 Eu1 N5 111.51(5) . . ?
N3 Eu1 N5 118.06(5) . . ?
O1 Eu1 N2 117.40(5) . . ?
O2 Eu1 N2 73.38(5) . . ?
N4 Eu1 N2 120.55(5) . . ?
O4 Eu1 N2 107.04(5) . . ?
O5 Eu1 N2 63.74(5) . . ?
N3 Eu1 N2 63.56(5) . . ?
N5 Eu1 N2 174.73(5) . . ?
O1 Eu1 N1 72.48(5) . . ?
O2 Eu1 N1 69.99(5) . . ?
N4 Eu1 N1 141.23(5) . . ?
O4 Eu1 N1 132.79(5) . . ?
O5 Eu1 N1 88.67(5) . . ?
N3 Eu1 N1 125.47(5) . . ?
N5 Eu1 N1 116.46(5) . . ?
N2 Eu1 N1 62.23(5) . . ?
O1 Eu1 N6 88.30(5) . . ?
O2 Eu1 N6 130.24(5) . . ?
N4 Eu1 N6 126.15(5) . . ?
O4 Eu1 N6 73.05(5) . . ?
O5 Eu1 N6 70.18(5) . . ?
N3 Eu1 N6 138.77(5) . . ?
N5 Eu1 N6 62.37(5) . . ?
N2 Eu1 N6 112.88(5) . . ?
N1 Eu1 N6 70.99(5) . . ?
O1 Eu1 N7 25.56(4) . . ?
O2 Eu1 N7 25.72(4) . . ?
N4 Eu1 N7 74.43(5) . . ?
O4 Eu1 N7 155.97(4) . . ?
O5 Eu1 N7 153.50(4) . . ?
N3 Eu1 N7 112.57(5) . . ?
N5 Eu1 N7 89.42(5) . . ?
N2 Eu1 N7 94.49(5) . . ?
N1 Eu1 N7 66.87(5) . . ?
N6 Eu1 N7 108.65(5) . . ?
O1 Eu1 N8 154.44(4) . . ?
O2 Eu1 N8 154.44(4) . . ?
N4 Eu1 N8 107.10(5) . . ?
O4 Eu1 N8 25.26(4) . . ?
O5 Eu1 N8 25.19(4) . . ?
N3 Eu1 N8 68.34(5) . . ?
N5 Eu1 N8 91.19(5) . . ?
N2 Eu1 N8 84.82(5) . . ?
N1 Eu1 N8 111.61(5) . . ?
N6 Eu1 N8 70.43(5) . . ?
N7 Eu1 N8 178.47(5) . . ?
F4 P1 F3 91.33(10) . . ?
F4 P1 F6 91.89(12) . . ?
F3 P1 F6 90.07(9) . . ?
F4 P1 F5 91.25(11) . . ?
F3 P1 F5 89.79(8) . . ?
F6 P1 F5 176.85(10) . . ?
F4 P1 F1 90.96(10) . . ?
F3 P1 F1 177.70(9) . . ?
F6 P1 F1 89.68(8) . . ?
F5 P1 F1 90.33(7) . . ?
F4 P1 F2 178.63(11) . . ?
F3 P1 F2 89.57(8) . . ?
F6 P1 F2 89.13(10) . . ?
F5 P1 F2 87.72(8) . . ?
F1 P1 F2 88.14(8) . . ?
N7 O1 Eu1 96.55(10) . . ?
N7 O2 Eu1 95.32(10) . . ?
N8 O4 Eu1 96.45(10) . . ?
N8 O5 Eu1 96.53(10) . . ?
C5 N1 C1 118.25(16) . . ?
C5 N1 Eu1 122.07(12) . . ?
C1 N1 Eu1 119.48(12) . . ?
C6 N2 C10 118.27(16) . . ?
C6 N2 Eu1 121.65(12) . . ?
C10 N2 Eu1 117.40(12) . . ?
C11 N3 C12 117.55(17) . . ?
C11 N3 Eu1 119.82(13) . . ?
C12 N3 Eu1 121.93(12) . . ?
C15 N4 C14 118.05(17) . . ?
C15 N4 Eu1 120.87(13) . . ?
C14 N4 Eu1 120.58(12) . . ?
C20 N5 C16 118.51(16) . . ?
C20 N5 Eu1 122.59(12) . . ?
C16 N5 Eu1 118.30(12) . . ?
C25 N6 C21 117.91(17) . . ?
C25 N6 Eu1 120.35(12) . . ?
C21 N6 Eu1 121.72(12) . . ?
O3 N7 O2 121.99(16) . . ?
O3 N7 O1 121.77(16) . . ?
O2 N7 O1 116.22(15) . . ?
O3 N7 Eu1 171.29(13) . . ?
O2 N7 Eu1 58.96(9) . . ?
O1 N7 Eu1 57.89(8) . . ?
O6 N8 O5 121.85(17) . . ?
O6 N8 O4 121.67(17) . . ?
O5 N8 O4 116.48(15) . . ?
O6 N8 Eu1 177.66(13) . . ?
O5 N8 Eu1 58.28(9) . . ?
O4 N8 Eu1 58.29(9) . . ?
N1 C1 C2 122.95(19) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.65(19) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.28(19) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C5 118.96(19) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.89(17) . . ?
N1 C5 C6 115.98(16) . . ?
C4 C5 C6 122.12(17) . . ?
N2 C6 C7 121.68(17) . . ?
N2 C6 C5 115.74(16) . . ?
C7 C6 C5 122.57(17) . . ?
C8 C7 C6 119.52(18) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 119.08(18) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C10 C9 C8 118.22(18) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N2 C10 C9 123.20(18) . . ?
N2 C10 C11 116.20(16) . . ?
C9 C10 C11 120.53(17) . . ?
N3 C11 C10 120.44(17) . . ?
N3 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
N3 C12 C13 111.86(16) . . ?
N3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 113.24(16) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
N4 C14 C13 110.87(16) . . ?
N4 C14 H14A 109.5 . . ?
C13 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
N4 C15 C16 119.67(18) . . ?
N4 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
N5 C16 C17 122.88(19) . . ?
N5 C16 C15 116.48(17) . . ?
C17 C16 C15 120.62(18) . . ?
C16 C17 C18 118.23(19) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 119.41(18) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 119.10(19) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
N5 C20 C19 121.79(18) . . ?
N5 C20 C21 116.38(16) . . ?
C19 C20 C21 121.83(17) . . ?
N6 C21 C22 121.81(18) . . ?
N6 C21 C20 116.21(16) . . ?
C22 C21 C20 121.98(17) . . ?
C23 C22 C21 119.46(18) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
C24 C23 C22 119.00(18) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 118.45(19) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
N6 C25 C24 123.35(19) . . ?
N6 C25 H25 118.3 . . ?
C24 C25 H25 118.3 . . ?
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 179.6(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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Eu1 O2 N7 O3 169.84(15) . . . . ?
Eu1 O2 N7 O1 -8.87(16) . . . . ?
Eu1 O1 N7 O3 -169.74(15) . . . . ?
Eu1 O1 N7 O2 8.97(16) . . . . ?
Eu1 O5 N8 O6 177.25(15) . . . . ?
Eu1 O5 N8 O4 -3.34(16) . . . . ?
Eu1 O4 N8 O6 -177.25(15) . . . . ?
Eu1 O4 N8 O5 3.34(16) . . . . ?
C5 N1 C1 C2 1.0(3) . . . . ?
Eu1 N1 C1 C2 -173.95(15) . . . . ?
N1 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C1 N1 C5 C4 -1.5(3) . . . . ?
Eu1 N1 C5 C4 173.29(14) . . . . ?
C1 N1 C5 C6 179.39(16) . . . . ?
Eu1 N1 C5 C6 -5.8(2) . . . . ?
C3 C4 C5 N1 1.0(3) . . . . ?
C3 C4 C5 C6 -179.99(18) . . . . ?
C10 N2 C6 C7 0.0(3) . . . . ?
Eu1 N2 C6 C7 160.94(14) . . . . ?
C10 N2 C6 C5 -179.14(16) . . . . ?
Eu1 N2 C6 C5 -18.2(2) . . . . ?
N1 C5 C6 N2 15.4(2) . . . . ?
C4 C5 C6 N2 -163.72(17) . . . . ?
N1 C5 C6 C7 -163.75(17) . . . . ?
C4 C5 C6 C7 17.1(3) . . . . ?
N2 C6 C7 C8 -1.4(3) . . . . ?
C5 C6 C7 C8 177.66(17) . . . . ?
C6 C7 C8 C9 1.5(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?
C6 N2 C10 C9 1.4(3) . . . . ?
Eu1 N2 C10 C9 -160.36(14) . . . . ?
C6 N2 C10 C11 178.37(16) . . . . ?
Eu1 N2 C10 C11 16.6(2) . . . . ?
C8 C9 C10 N2 -1.3(3) . . . . ?
C8 C9 C10 C11 -178.16(17) . . . . ?
C12 N3 C11 C10 -177.60(16) . . . . ?
Eu1 N3 C11 C10 -7.0(2) . . . . ?
N2 C10 C11 N3 -6.7(3) . . . . ?
C9 C10 C11 N3 170.32(18) . . . . ?
C11 N3 C12 C13 -109.6(2) . . . . ?
Eu1 N3 C12 C13 79.99(18) . . . . ?
N3 C12 C13 C14 -39.1(2) . . . . ?
C15 N4 C14 C13 -103.4(2) . . . . ?
Eu1 N4 C14 C13 84.71(17) . . . . ?
C12 C13 C14 N4 -38.0(2) . . . . ?
C14 N4 C15 C16 -179.74(16) . . . . ?
Eu1 N4 C15 C16 -7.9(2) . . . . ?
C20 N5 C16 C17 -1.0(3) . . . . ?
Eu1 N5 C16 C17 -172.38(14) . . . . ?
C20 N5 C16 C15 177.24(16) . . . . ?
Eu1 N5 C16 C15 5.9(2) . . . . ?
N4 C15 C16 N5 1.1(3) . . . . ?
N4 C15 C16 C17 179.43(18) . . . . ?
N5 C16 C17 C18 2.6(3) . . . . ?
C15 C16 C17 C18 -175.61(18) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C17 C18 C19 C20 -1.0(3) . . . . ?
C16 N5 C20 C19 -1.6(3) . . . . ?
Eu1 N5 C20 C19 169.32(14) . . . . ?
C16 N5 C20 C21 178.62(16) . . . . ?
Eu1 N5 C20 C21 -10.4(2) . . . . ?
C18 C19 C20 N5 2.7(3) . . . . ?
C18 C19 C20 C21 -177.61(18) . . . . ?
C25 N6 C21 C22 -1.0(3) . . . . ?
Eu1 N6 C21 C22 177.26(14) . . . . ?
C25 N6 C21 C20 179.66(17) . . . . ?
Eu1 N6 C21 C20 -2.0(2) . . . . ?
N5 C20 C21 N6 7.9(2) . . . . ?
C19 C20 C21 N6 -171.82(18) . . . . ?
N5 C20 C21 C22 -171.36(17) . . . . ?
C19 C20 C21 C22 8.9(3) . . . . ?
N6 C21 C22 C23 1.5(3) . . . . ?
C20 C21 C22 C23 -179.29(18) . . . . ?
C21 C22 C23 C24 -0.6(3) . . . . ?
C22 C23 C24 C25 -0.5(3) . . . . ?
C21 N6 C25 C24 -0.2(3) . . . . ?
Eu1 N6 C25 C24 -178.48(15) . . . . ?
C23 C24 C25 N6 0.9(3) . . . . ?

_refine_diff_density_max         1.193
_refine_diff_density_min         -0.573
_refine_diff_density_rms         0.070

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_e6001
_database_code_depnum_ccdc_archive 'CCDC 1861234'
loop_
_audit_author_name
_audit_author_address
'Shuhei Ogata, Miki Hasegawa'
;Aoyama Gakuin University
Japan
;
_audit_update_record             
;
2018-08-09 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 Eu F6 N9 O6 P'
_chemical_formula_weight         868.49

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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.
;

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'

_cell_length_a                   24.708(3)
_cell_length_b                   12.1202(12)
_cell_length_c                   24.378(3)
_cell_angle_alpha                90
_cell_angle_beta                 119.7230(10)
_cell_angle_gamma                90
_cell_volume                     6339.9(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    90(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.820
_exptl_crystal_F_000             3440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.303
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.197
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   0.566
_shelx_estimated_absorpt_T_max   0.680
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34970
_diffrn_reflns_av_unetI/netI     0.0208
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.898
_diffrn_reflns_theta_max         27.558
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7276
_reflns_number_gt                6923
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+66.7607P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7276
_refine_ls_number_parameters     458
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0950
_refine_ls_goodness_of_fit_ref   1.394
_refine_ls_restrained_S_all      1.399
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.001

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
Eu1 Eu 0.68255(2) 0.48841(2) 0.37783(2) 0.01858(7) Uani 1 1 d . . . . .
C1 C 0.7445(2) 0.6785(4) 0.3167(2) 0.0227(10) Uani 1 1 d . . . . .
H1 H 0.7708 0.6162 0.3250 0.027 Uiso 1 1 calc R U . . .
C2 C 0.7560(2) 0.7709(4) 0.2909(2) 0.0240(10) Uani 1 1 d . . . . .
H2 H 0.7891 0.7721 0.2817 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7176(3) 0.8617(4) 0.2787(2) 0.0301(11) Uani 1 1 d . . . . .
H3 H 0.7239 0.9265 0.2605 0.036 Uiso 1 1 calc R U . . .
C4 C 0.6702(3) 0.8571(4) 0.2931(2) 0.0315(12) Uani 1 1 d . . . . .
H4 H 0.6437 0.9189 0.2854 0.038 Uiso 1 1 calc R U . . .
C5 C 0.6618(2) 0.7604(4) 0.3191(2) 0.0237(10) Uani 1 1 d . . . . .
C6 C 0.6090(2) 0.7469(5) 0.3316(2) 0.0284(11) Uani 1 1 d . . . . .
C7 C 0.5683(3) 0.8339(6) 0.3236(3) 0.0419(16) Uani 1 1 d . . . . .
H7 H 0.5768 0.9064 0.3149 0.050 Uiso 1 1 calc R U . . .
C8 C 0.5162(3) 0.8131(7) 0.3283(3) 0.052(2) Uani 1 1 d . . . . .
H8 H 0.4880 0.8710 0.3229 0.062 Uiso 1 1 calc R U . . .
C9 C 0.5052(3) 0.7077(7) 0.3410(3) 0.0478(19) Uani 1 1 d . . . . .
H9 H 0.4685 0.6909 0.3426 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5489(2) 0.6256(6) 0.3514(2) 0.0354(14) Uani 1 1 d . . . . .
C11 C 0.5402(3) 0.5127(6) 0.3656(3) 0.0436(16) Uani 1 1 d . . . . .
H11 H 0.5024 0.4917 0.3642 0.052 Uiso 1 1 calc R U . . .
C12 C 0.5676(4) 0.3278(6) 0.3847(4) 0.065(2) Uani 1 1 d D . . . .
C13 C 0.5837(4) 0.2570(6) 0.3425(4) 0.066(3) Uani 1 1 d D . . . .
C14 C 0.6833(3) 0.2126(4) 0.3574(3) 0.0325(12) Uani 1 1 d . . . . .
H14 H 0.6688 0.1388 0.3472 0.039 Uiso 1 1 calc DR U . . .
C15 C 0.7469(3) 0.2402(4) 0.3727(2) 0.0259(10) Uani 1 1 d . . . . .
C16 C 0.7842(3) 0.1665(4) 0.3630(2) 0.0309(12) Uani 1 1 d . . . . .
H16 H 0.7689 0.0956 0.3457 0.037 Uiso 1 1 calc R U . . .
C17 C 0.8437(3) 0.1978(4) 0.3790(3) 0.0334(12) Uani 1 1 d . . . . .
H17 H 0.8696 0.1502 0.3712 0.040 Uiso 1 1 calc R U . . .
C18 C 0.8653(3) 0.3003(4) 0.4069(3) 0.0293(11) Uani 1 1 d . . . . .
H18 H 0.9066 0.3230 0.4193 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8256(2) 0.3692(4) 0.4165(2) 0.0208(9) Uani 1 1 d . . . . .
C20 C 0.8461(2) 0.4774(4) 0.4495(2) 0.0201(9) Uani 1 1 d . . . . .
C21 C 0.9086(2) 0.5027(4) 0.4886(2) 0.0249(10) Uani 1 1 d . . . . .
H21 H 0.9400 0.4522 0.4931 0.030 Uiso 1 1 calc R U . . .
C22 C 0.9247(2) 0.6015(4) 0.5206(2) 0.0267(10) Uani 1 1 d . . . . .
H22 H 0.9672 0.6197 0.5480 0.032 Uiso 1 1 calc R U . . .
C23 C 0.8778(2) 0.6739(4) 0.5124(2) 0.0226(10) Uani 1 1 d . . . . .
H23 H 0.8875 0.7424 0.5341 0.027 Uiso 1 1 calc R U . . .
C24 C 0.8166(2) 0.6441(4) 0.4718(2) 0.0199(9) Uani 1 1 d . . . . .
H24 H 0.7846 0.6948 0.4652 0.024 Uiso 1 1 calc R U . . .
C26 C 0.9586(3) 0.8780(5) 0.4937(3) 0.0336(12) Uani 1 1 d . . . . .
C27 C 0.8977(3) 0.9034(6) 0.4413(3) 0.0462(16) Uani 1 1 d . . . . .
H27A H 0.8872 0.8506 0.4070 0.069 Uiso 1 1 calc R U . . .
H27B H 0.8979 0.9783 0.4262 0.069 Uiso 1 1 calc R U . . .
H27C H 0.8666 0.8987 0.4551 0.069 Uiso 1 1 calc R U . . .
N1 N 0.69852(18) 0.6711(3) 0.33097(18) 0.0206(8) Uani 1 1 d . . . . .
N2 N 0.60042(18) 0.6456(4) 0.34749(19) 0.0273(9) Uani 1 1 d . . . . .
N3 N 0.5829(2) 0.4426(4) 0.3799(2) 0.0378(12) Uani 1 1 d . . . . .
N4 N 0.6477(2) 0.2873(4) 0.3579(2) 0.0331(11) Uani 1 1 d . . . . .
N5 N 0.76677(19) 0.3410(3) 0.39799(19) 0.0215(8) Uani 1 1 d . . . . .
N6 N 0.80027(17) 0.5472(3) 0.44143(18) 0.0183(8) Uani 1 1 d . . . . .
N7 N 0.72468(19) 0.5201(4) 0.51202(19) 0.0259(9) Uani 1 1 d . . . . .
N8 N 0.63685(19) 0.4682(3) 0.24272(19) 0.0220(8) Uani 1 1 d . . . . .
N9 N 1.0059(3) 0.8587(5) 0.5359(3) 0.0522(15) Uani 1 1 d . . . . .
O1 O 0.72904(16) 0.4265(3) 0.49105(16) 0.0259(7) Uani 1 1 d . . . . .
O2 O 0.69511(16) 0.5954(3) 0.47079(16) 0.0239(7) Uani 1 1 d . . . . .
O3 O 0.7475(2) 0.5397(4) 0.56859(18) 0.0414(10) Uani 1 1 d . . . . .
O4 O 0.69253(15) 0.4442(3) 0.28287(16) 0.0230(7) Uani 1 1 d . . . . .
O5 O 0.59936(15) 0.4834(3) 0.26365(16) 0.0278(8) Uani 1 1 d . . . . .
O6 O 0.61985(18) 0.4811(3) 0.18664(16) 0.0325(8) Uani 1 1 d . . . . .
F1 F 0.58735(19) -0.0185(3) 0.15356(17) 0.0504(10) Uani 1 1 d . . . . .
F2 F 0.60809(19) 0.1528(3) 0.12800(17) 0.0516(10) Uani 1 1 d . . . . .
F3 F 0.65539(14) 0.0988(3) 0.22981(15) 0.0371(8) Uani 1 1 d . . . . .
F4 F 0.56298(17) 0.0596(3) 0.2215(2) 0.0511(10) Uani 1 1 d . . . . .
F5 F 0.58127(18) 0.2295(3) 0.19528(19) 0.0488(9) Uani 1 1 d . . . . .
F6 F 0.51432(18) 0.1143(4) 0.1195(2) 0.0770(16) Uani 1 1 d . . . . .
P1 P 0.58500(6) 0.10707(11) 0.17378(7) 0.0283(3) Uani 1 1 d . . . . .
C25A C 0.5902(11) 0.1364(11) 0.3637(11) 0.052(2) Uani 0.288(10) 1 d D . P A 2
H25A H 0.5875 0.0883 0.3301 0.078 Uiso 0.288(10) 1 calc DR U P A 2
H25B H 0.5567 0.1179 0.3726 0.078 Uiso 0.288(10) 1 calc R U P A 2
H25C H 0.6307 0.1258 0.4020 0.078 Uiso 0.288(10) 1 calc R U P A 2
C25 C 0.5991(4) 0.2922(8) 0.4492(4) 0.052(2) Uani 0.712(10) 1 d D . P A 1
H25D H 0.6441 0.3025 0.4672 0.078 Uiso 0.712(10) 1 calc R U P A 1
H25E H 0.5902 0.2140 0.4512 0.078 Uiso 0.712(10) 1 calc R U P A 1
H25F H 0.5846 0.3358 0.4732 0.078 Uiso 0.712(10) 1 calc R U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Eu1 O2 2.493(3) . ?
Eu1 O4 2.504(3) . ?
Eu1 O5 2.511(3) . ?
Eu1 O1 2.521(3) . ?
Eu1 N3 2.548(4) . ?
Eu1 N4 2.550(4) . ?
Eu1 N5 2.598(4) . ?
Eu1 N2 2.609(4) . ?
Eu1 N1 2.610(4) . ?
Eu1 N6 2.627(4) . ?
Eu1 N8 2.915(4) . ?
Eu1 N7 2.925(4) . ?
C1 N1 1.345(6) . ?
C1 C2 1.382(7) . ?
C2 C3 1.385(7) . ?
C3 C4 1.382(8) . ?
C4 C5 1.396(7) . ?
C5 N1 1.348(6) . ?
C5 C6 1.488(7) . ?
C6 N2 1.336(7) . ?
C6 C7 1.402(7) . ?
C7 C8 1.374(10) . ?
C8 C9 1.372(11) . ?
C9 C10 1.396(9) . ?
C10 N2 1.345(7) . ?
C10 C11 1.454(10) . ?
C11 N3 1.262(8) . ?
C12 C25 1.431(8) . ?
C12 N3 1.463(8) . ?
C12 C13 1.535(9) . ?
C13 N4 1.481(7) . ?
C13 C25A 1.532(10) . ?
C14 N4 1.266(8) . ?
C14 C15 1.462(8) . ?
C15 N5 1.347(6) . ?
C15 C16 1.385(7) . ?
C16 C17 1.374(8) . ?
C17 C18 1.389(7) . ?
C18 C19 1.394(7) . ?
C19 N5 1.335(6) . ?
C19 C20 1.490(6) . ?
C20 N6 1.346(6) . ?
C20 C21 1.389(6) . ?
C21 C22 1.376(7) . ?
C22 C23 1.386(7) . ?
C23 C24 1.384(6) . ?
C24 N6 1.339(6) . ?
C26 N9 1.134(8) . ?
C26 C27 1.445(8) . ?
N7 O3 1.227(5) . ?
N7 O1 1.271(6) . ?
N7 O2 1.284(5) . ?
N8 O6 1.225(5) . ?
N8 O4 1.265(5) . ?
N8 O5 1.273(5) . ?
F1 P1 1.610(3) . ?
F2 P1 1.584(4) . ?
F3 P1 1.595(3) . ?
F4 P1 1.615(4) . ?
F5 P1 1.591(3) . ?
F6 P1 1.586(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
O2 Eu1 O4 157.89(11) . . ?
O2 Eu1 O5 133.22(11) . . ?
O4 Eu1 O5 51.08(11) . . ?
O2 Eu1 O1 51.38(11) . . ?
O4 Eu1 O1 138.43(11) . . ?
O5 Eu1 O1 152.22(11) . . ?
O2 Eu1 N3 77.38(13) . . ?
O4 Eu1 N3 120.68(13) . . ?
O5 Eu1 N3 75.43(14) . . ?
O1 Eu1 N3 80.44(15) . . ?
O2 Eu1 N4 123.26(13) . . ?
O4 Eu1 N4 78.35(13) . . ?
O5 Eu1 N4 75.66(14) . . ?
O1 Eu1 N4 81.47(13) . . ?
N3 Eu1 N4 63.75(16) . . ?
O2 Eu1 N5 117.30(12) . . ?
O4 Eu1 N5 65.87(12) . . ?
O5 Eu1 N5 109.38(12) . . ?
O1 Eu1 N5 72.59(12) . . ?
N3 Eu1 N5 122.52(15) . . ?
N4 Eu1 N5 62.72(14) . . ?
O2 Eu1 N2 66.84(12) . . ?
O4 Eu1 N2 108.26(12) . . ?
O5 Eu1 N2 66.99(12) . . ?
O1 Eu1 N2 113.31(12) . . ?
N3 Eu1 N2 62.69(16) . . ?
N4 Eu1 N2 120.16(15) . . ?
N5 Eu1 N2 173.37(13) . . ?
O2 Eu1 N1 88.80(12) . . ?
O4 Eu1 N1 70.81(12) . . ?
O5 Eu1 N1 75.73(12) . . ?
O1 Eu1 N1 130.24(12) . . ?
N3 Eu1 N1 123.40(15) . . ?
N4 Eu1 N1 146.88(14) . . ?
N5 Eu1 N1 112.68(12) . . ?
N2 Eu1 N1 61.41(13) . . ?
O2 Eu1 N6 73.75(11) . . ?
O4 Eu1 N6 90.92(11) . . ?
O5 Eu1 N6 136.00(12) . . ?
O1 Eu1 N6 70.39(11) . . ?
N3 Eu1 N6 147.71(14) . . ?
N4 Eu1 N6 122.81(14) . . ?
N5 Eu1 N6 61.72(12) . . ?
N2 Eu1 N6 116.58(13) . . ?
N1 Eu1 N6 70.42(12) . . ?
O2 Eu1 N8 151.01(11) . . ?
O4 Eu1 N8 25.58(11) . . ?
O5 Eu1 N8 25.79(11) . . ?
O1 Eu1 N8 157.38(11) . . ?
N3 Eu1 N8 99.61(14) . . ?
N4 Eu1 N8 78.43(13) . . ?
N5 Eu1 N8 88.93(12) . . ?
N2 Eu1 N8 85.97(12) . . ?
N1 Eu1 N8 68.56(12) . . ?
N6 Eu1 N8 112.64(12) . . ?
O2 Eu1 N7 25.87(12) . . ?
O4 Eu1 N7 156.68(11) . . ?
O5 Eu1 N7 152.23(11) . . ?
O1 Eu1 N7 25.63(12) . . ?
N3 Eu1 N7 79.53(14) . . ?
N4 Eu1 N7 103.77(14) . . ?
N5 Eu1 N7 94.08(12) . . ?
N2 Eu1 N7 90.95(12) . . ?
N1 Eu1 N7 109.33(12) . . ?
N6 Eu1 N7 68.18(11) . . ?
N8 Eu1 N7 176.85(12) . . ?
N1 C1 C2 124.2(5) . . ?
C1 C2 C3 118.0(5) . . ?
C4 C3 C2 119.3(5) . . ?
C3 C4 C5 119.0(5) . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 C6 115.6(5) . . ?
C4 C5 C6 121.8(5) . . ?
N2 C6 C7 121.8(5) . . ?
N2 C6 C5 116.2(4) . . ?
C7 C6 C5 121.9(5) . . ?
C8 C7 C6 119.2(7) . . ?
C9 C8 C7 119.2(6) . . ?
C8 C9 C10 119.0(6) . . ?
N2 C10 C9 122.2(6) . . ?
N2 C10 C11 116.4(5) . . ?
C9 C10 C11 121.5(6) . . ?
N3 C11 C10 119.7(5) . . ?
C25 C12 N3 110.7(7) . . ?
C25 C12 C13 112.8(8) . . ?
N3 C12 C13 108.3(5) . . ?
N4 C13 C12 106.9(5) . . ?
N4 C13 C25A 103.3(10) . . ?
C12 C13 C25A 109.1(11) . . ?
N4 C14 C15 119.8(5) . . ?
N5 C15 C16 122.8(5) . . ?
N5 C15 C14 115.2(5) . . ?
C16 C15 C14 122.1(5) . . ?
C17 C16 C15 118.8(5) . . ?
C16 C17 C18 118.9(5) . . ?
C17 C18 C19 119.1(5) . . ?
N5 C19 C18 121.9(4) . . ?
N5 C19 C20 115.4(4) . . ?
C18 C19 C20 122.6(4) . . ?
N6 C20 C21 122.1(4) . . ?
N6 C20 C19 116.0(4) . . ?
C21 C20 C19 121.9(4) . . ?
C22 C21 C20 119.4(4) . . ?
C21 C22 C23 118.9(4) . . ?
C24 C23 C22 118.5(4) . . ?
N6 C24 C23 123.2(4) . . ?
N9 C26 C27 178.3(7) . . ?
C1 N1 C5 117.1(4) . . ?
C1 N1 Eu1 120.0(3) . . ?
C5 N1 Eu1 122.9(3) . . ?
C6 N2 C10 118.6(5) . . ?
C6 N2 Eu1 122.7(3) . . ?
C10 N2 Eu1 118.6(4) . . ?
C11 N3 C12 116.6(5) . . ?
C11 N3 Eu1 122.2(4) . . ?
C12 N3 Eu1 120.0(4) . . ?
C14 N4 C13 118.7(5) . . ?
C14 N4 Eu1 121.0(3) . . ?
C13 N4 Eu1 120.2(4) . . ?
C19 N5 C15 118.4(4) . . ?
C19 N5 Eu1 121.5(3) . . ?
C15 N5 Eu1 117.5(3) . . ?
C24 N6 C20 117.9(4) . . ?
C24 N6 Eu1 120.4(3) . . ?
C20 N6 Eu1 121.4(3) . . ?
O3 N7 O1 122.8(4) . . ?
O3 N7 O2 120.5(4) . . ?
O1 N7 O2 116.6(4) . . ?
O3 N7 Eu1 173.2(3) . . ?
O1 N7 Eu1 59.1(2) . . ?
O2 N7 Eu1 57.9(2) . . ?
O6 N8 O4 122.2(4) . . ?
O6 N8 O5 120.9(4) . . ?
O4 N8 O5 116.8(4) . . ?
O6 N8 Eu1 167.7(3) . . ?
O4 N8 Eu1 58.8(2) . . ?
O5 N8 Eu1 59.1(2) . . ?
N7 O1 Eu1 95.2(3) . . ?
N7 O2 Eu1 96.2(3) . . ?
N8 O4 Eu1 95.6(2) . . ?
N8 O5 Eu1 95.1(3) . . ?
F2 P1 F6 91.4(3) . . ?
F2 P1 F5 90.3(2) . . ?
F6 P1 F5 90.2(2) . . ?
F2 P1 F3 90.3(2) . . ?
F6 P1 F3 178.3(3) . . ?
F5 P1 F3 89.6(2) . . ?
F2 P1 F1 92.0(2) . . ?
F6 P1 F1 89.3(2) . . ?
F5 P1 F1 177.6(2) . . ?
F3 P1 F1 90.7(2) . . ?
F2 P1 F4 178.7(2) . . ?
F6 P1 F4 89.8(3) . . ?
F5 P1 F4 90.0(2) . . ?
F3 P1 F4 88.5(2) . . ?
F1 P1 F4 87.7(2) . . ?

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
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655
C2 H2 F3 0.95 2.60 3.240(6) 125.2 4_655
C4 H4 F4 0.95 2.50 3.391(6) 156.9 1_565
C11 H11 O6 0.95 2.64 3.523(7) 154.7 2_655
C24 H24 O2 0.95 2.58 3.047(6) 110.6 .
C27 H27A F2 0.98 2.57 3.444(8) 149.1 4_655
C27 H27B O6 0.98 2.56 3.076(7) 112.7 4_655
C25A H25A F4 0.98 2.43 3.32(2) 150.8 .
C25A H25B F6 0.98 1.86 2.82(2) 166.6 2_655
C25 H25D O1 0.98 2.41 3.278(9) 147.9 .
C25 H25E F6 0.98 2.59 3.265(10) 126.4 2_655

_refine_diff_density_max         1.191
_refine_diff_density_min         -1.886
_refine_diff_density_rms         0.116

_shelxl_version_number           2014/6


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1861236'
loop_
_audit_author_name
_audit_author_address
'Shuhei Ogata, Miki Hasegawa'
;Aoyama Gakuin University
Japan
;
_audit_update_record             
;
2018-08-09 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 Eu F6 N8 O6 P'
_chemical_formula_weight         855.49

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'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   16.7522(18)
_cell_length_b                   14.5415(15)
_cell_length_c                   25.718(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6264.8(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9750
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.62

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.814
_exptl_crystal_F_000             3392
_exptl_transmission_factor_min   1.567
_exptl_transmission_factor_max   2.062
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.365
_exptl_crystal_size_min          0.234
_exptl_absorpt_coefficient_mu    2.145
_shelx_estimated_absorpt_T_min   0.481
_shelx_estimated_absorpt_T_max   0.634
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            66557
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         1.584
_diffrn_reflns_theta_max         27.635
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7265
_reflns_number_gt                6395
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0207P)²+9.1262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7265
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0228
_refine_ls_wR_factor_ref         0.0565
_refine_ls_wR_factor_gt          0.0534
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Eu1 Eu 0.91276(2) 0.70221(2) 0.42037(2) 0.01167(4) Uani 1 1 d . . . . .
P1 P 0.09277(4) 0.04321(5) 0.32130(3) 0.02692(14) Uani 1 1 d . . . . .
O1 O 0.76612(9) 0.74051(11) 0.41503(6) 0.0170(3) Uani 1 1 d . . . . .
O2 O 0.80522(9) 0.63404(10) 0.36198(6) 0.0172(3) Uani 1 1 d . . . . .
O3 O 0.68902(10) 0.69836(11) 0.35096(6) 0.0209(3) Uani 1 1 d . . . . .
O4 O 1.03904(9) 0.78318(10) 0.44908(6) 0.0164(3) Uani 1 1 d . . . . .
O5 O 1.03086(9) 0.63778(10) 0.46727(6) 0.0171(3) Uani 1 1 d . . . . .
O6 O 1.13463(10) 0.71661(11) 0.49232(7) 0.0227(4) Uani 1 1 d . . . . .
N1 N 0.88408(11) 0.81002(12) 0.34025(7) 0.0163(4) Uani 1 1 d . . . . .
N2 N 0.88653(11) 0.87310(12) 0.43911(7) 0.0148(4) Uani 1 1 d . . . . .
N3 N 0.89927(10) 0.74866(13) 0.51667(7) 0.0161(4) Uani 1 1 d . . . . .
N4 N 0.84211(10) 0.57807(13) 0.47265(7) 0.0147(4) Uani 1 1 d . . . . .
N5 N 0.93724(10) 0.53752(12) 0.38998(7) 0.0134(3) Uani 1 1 d . . . . .
N6 N 1.01858(11) 0.67832(13) 0.35003(7) 0.0156(4) Uani 1 1 d . . . . .
N7 N 0.75150(11) 0.69095(12) 0.37534(7) 0.0152(4) Uani 1 1 d . . . . .
N8 N 1.07022(11) 0.71249(12) 0.47012(7) 0.0153(4) Uani 1 1 d . . . . .
F1 F 0.02345(12) -0.02231(14) 0.29992(7) 0.0529(5) Uani 1 1 d . . . . .
F2 F 0.11141(18) 0.07502(17) 0.26457(8) 0.0840(8) Uani 1 1 d . . . . .
F3 F 0.03127(17) 0.12366(17) 0.32801(15) 0.1145(12) Uani 1 1 d . . . . .
F4 F 0.16027(13) 0.10754(15) 0.34405(9) 0.0672(6) Uani 1 1 d . . . . .
F5 F 0.07038(15) 0.00873(19) 0.37804(7) 0.0740(7) Uani 1 1 d . . . . .
F6 F 0.15354(12) -0.03937(13) 0.31681(9) 0.0601(6) Uani 1 1 d . . . . .
C1 C 0.87079(14) 0.77388(16) 0.29288(9) 0.0203(5) Uani 1 1 d . . . . .
H1 H 0.8912 0.7143 0.2856 0.024 Uiso 1 1 calc R U . . .
C2 C 0.82874(15) 0.81927(18) 0.25410(9) 0.0253(5) Uani 1 1 d . . . . .
H2 H 0.8208 0.7914 0.2211 0.030 Uiso 1 1 calc R U . . .
C3 C 0.79866(15) 0.90594(17) 0.26452(10) 0.0262(5) Uani 1 1 d . . . . .
H3 H 0.7677 0.9376 0.2393 0.031 Uiso 1 1 calc R U . . .
C4 C 0.81445(14) 0.94596(16) 0.31236(9) 0.0219(5) Uani 1 1 d . . . . .
H4 H 0.7958 1.0061 0.3201 0.026 Uiso 1 1 calc R U . . .
C5 C 0.85815(13) 0.89637(15) 0.34887(8) 0.0163(4) Uani 1 1 d . . . . .
C6 C 0.87659(12) 0.93451(15) 0.40112(9) 0.0156(4) Uani 1 1 d . . . . .
C7 C 0.88289(14) 1.02932(16) 0.40959(9) 0.0205(5) Uani 1 1 d . . . . .
H7 H 0.8778 1.0714 0.3815 0.025 Uiso 1 1 calc R U . . .
C8 C 0.89658(13) 1.06058(16) 0.45939(10) 0.0220(5) Uani 1 1 d . . . . .
H8 H 0.9019 1.1246 0.4661 0.026 Uiso 1 1 calc R U . . .
C9 C 0.90252(13) 0.99741(17) 0.49971(10) 0.0211(5) Uani 1 1 d . . . . .
H9 H 0.9097 1.0175 0.5346 0.025 Uiso 1 1 calc R U . . .
C10 C 0.89771(13) 0.90448(16) 0.48807(9) 0.0173(4) Uani 1 1 d . . . . .
C11 C 0.90270(13) 0.83364(17) 0.52875(9) 0.0185(4) Uani 1 1 d . . . . .
H11 H 0.9085 0.8512 0.5641 0.022 Uiso 1 1 calc R U . . .
C12 C 0.90360(13) 0.67988(17) 0.55838(9) 0.0192(5) Uani 1 1 d . . . . .
H12A H 0.9188 0.7107 0.5913 0.023 Uiso 1 1 calc R U . . .
H12B H 0.9457 0.6345 0.5499 0.023 Uiso 1 1 calc R U . . .
C13 C 0.82368(13) 0.62919(16) 0.56614(8) 0.0181(4) Uani 1 1 d . . . . .
C14 C 0.78533(13) 0.60301(16) 0.51379(8) 0.0172(4) Uani 1 1 d . . . . .
H14A H 0.7488 0.5505 0.5195 0.021 Uiso 1 1 calc R U . . .
H14B H 0.7527 0.6555 0.5015 0.021 Uiso 1 1 calc R U . . .
C15 C 0.84407(13) 0.49530(15) 0.45669(8) 0.0166(4) Uani 1 1 d . . . . .
H15 H 0.8134 0.4497 0.4740 0.020 Uiso 1 1 calc R U . . .
C16 C 0.89345(13) 0.46943(15) 0.41162(8) 0.0155(4) Uani 1 1 d . . . . .
C17 C 0.89057(14) 0.38144(15) 0.39140(9) 0.0186(4) Uani 1 1 d . . . . .
H17 H 0.8602 0.3348 0.4080 0.022 Uiso 1 1 calc R U . . .
C18 C 0.93326(14) 0.36272(16) 0.34610(9) 0.0208(5) Uani 1 1 d . . . . .
H18 H 0.9317 0.3032 0.3309 0.025 Uiso 1 1 calc R U . . .
C19 C 0.97780(13) 0.43214(15) 0.32373(9) 0.0188(4) Uani 1 1 d . . . . .
H19 H 1.0070 0.4210 0.2927 0.023 Uiso 1 1 calc R U . . .
C20 C 0.97957(12) 0.51912(15) 0.34710(8) 0.0140(4) Uani 1 1 d . . . . .
C21 C 1.02870(13) 0.59607(15) 0.32658(8) 0.0151(4) Uani 1 1 d . . . . .
C22 C 1.08277(14) 0.58443(17) 0.28645(9) 0.0219(5) Uani 1 1 d . . . . .
H22 H 1.0886 0.5261 0.2702 0.026 Uiso 1 1 calc R U . . .
C23 C 1.12849(16) 0.65852(18) 0.27006(9) 0.0269(5) Uani 1 1 d . . . . .
H23 H 1.1664 0.6514 0.2429 0.032 Uiso 1 1 calc R U . . .
C24 C 1.11800(14) 0.74262(17) 0.29381(9) 0.0226(5) Uani 1 1 d . . . . .
H24 H 1.1481 0.7946 0.2831 0.027 Uiso 1 1 calc R U . . .
C25 C 1.06270(14) 0.74987(15) 0.33365(9) 0.0194(4) Uani 1 1 d . . . . .
H25 H 1.0557 0.8078 0.3501 0.023 Uiso 1 1 calc R U . . .
C26 C 0.76428(15) 0.69062(18) 0.59528(9) 0.0248(5) Uani 1 1 d . . . . .
H26A H 0.7130 0.6587 0.5984 0.037 Uiso 1 1 calc R U . . .
H26B H 0.7568 0.7482 0.5760 0.037 Uiso 1 1 calc R U . . .
H26C H 0.7851 0.7042 0.6301 0.037 Uiso 1 1 calc R U . . .
C27 C 0.84033(15) 0.54244(18) 0.59795(10) 0.0264(5) Uani 1 1 d . . . . .
H27A H 0.8663 0.5594 0.6307 0.040 Uiso 1 1 calc R U . . .
H27B H 0.8754 0.5014 0.5782 0.040 Uiso 1 1 calc R U . . .
H27C H 0.7899 0.5109 0.6054 0.040 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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
Eu1 O5 2.4994(15) . ?
Eu1 O4 2.5311(15) . ?
Eu1 O1 2.5227(15) . ?
Eu1 N4 2.5430(18) . ?
Eu1 O2 2.5462(15) . ?
Eu1 N5 2.5523(17) . ?
Eu1 N6 2.5565(18) . ?
Eu1 N2 2.5692(18) . ?
Eu1 N3 2.5770(18) . ?
Eu1 N1 2.6333(18) . ?
Eu1 N8 2.9354(19) . ?
Eu1 N7 2.9437(19) . ?
P1 F6 1.5785(19) . ?
P1 F3 1.568(2) . ?
P1 F4 1.580(2) . ?
P1 F2 1.562(2) . ?
P1 F5 1.588(2) . ?
P1 F1 1.5995(19) . ?
O1 N7 1.273(2) . ?
O2 N7 1.270(2) . ?
O3 N7 1.225(2) . ?
O4 N8 1.274(2) . ?
O5 N8 1.273(2) . ?
O6 N8 1.222(2) . ?
N1 C5 1.347(3) . ?
N1 C1 1.345(3) . ?
N2 C6 1.334(3) . ?
N2 C10 1.352(3) . ?
N3 C11 1.276(3) . ?
N3 C12 1.468(3) . ?
N4 C15 1.272(3) . ?
N4 C14 1.468(3) . ?
N5 C20 1.338(3) . ?
N5 C16 1.352(3) . ?
N6 C25 1.344(3) . ?
N6 C21 1.350(3) . ?
C1 C2 1.388(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.384(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.392(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.486(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.378(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.471(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.541(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C27 1.529(3) . ?
C13 C26 1.533(3) . ?
C13 C14 1.540(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.473(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.382(3) . ?
C17 C18 1.394(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.401(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.486(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.387(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.378(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

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 Eu1 O4 51.10(5) . . ?
O5 Eu1 O1 151.63(5) . . ?
O4 Eu1 O1 136.64(5) . . ?
O5 Eu1 N4 81.21(5) . . ?
O4 Eu1 N4 124.40(5) . . ?
O1 Eu1 N4 74.47(5) . . ?
O5 Eu1 O2 134.33(5) . . ?
O4 Eu1 O2 160.82(5) . . ?
O1 Eu1 O2 50.57(5) . . ?
N4 Eu1 O2 72.91(5) . . ?
O5 Eu1 N5 70.66(5) . . ?
O4 Eu1 N5 113.05(5) . . ?
O1 Eu1 N5 110.30(5) . . ?
N4 Eu1 N5 64.57(6) . . ?
O2 Eu1 N5 64.39(5) . . ?
O5 Eu1 N6 75.03(5) . . ?
O4 Eu1 N6 71.95(5) . . ?
O1 Eu1 N6 131.81(5) . . ?
N4 Eu1 N6 126.90(6) . . ?
O2 Eu1 N6 91.17(5) . . ?
N5 Eu1 N6 62.90(6) . . ?
O5 Eu1 N2 114.05(5) . . ?
O4 Eu1 N2 68.80(5) . . ?
O1 Eu1 N2 68.29(5) . . ?
N4 Eu1 N2 120.52(6) . . ?
O2 Eu1 N2 111.48(5) . . ?
N5 Eu1 N2 172.97(6) . . ?
N6 Eu1 N2 112.50(6) . . ?
O5 Eu1 N3 72.78(5) . . ?
O4 Eu1 N3 70.79(5) . . ?
O1 Eu1 N3 84.78(5) . . ?
N4 Eu1 N3 68.72(6) . . ?
O2 Eu1 N3 127.36(5) . . ?
N5 Eu1 N3 123.66(6) . . ?
N6 Eu1 N3 140.94(6) . . ?
N2 Eu1 N3 63.34(6) . . ?
O5 Eu1 N1 138.18(5) . . ?
O4 Eu1 N1 95.96(5) . . ?
O1 Eu1 N1 69.41(5) . . ?
N4 Eu1 N1 138.71(6) . . ?
O2 Eu1 N1 68.97(5) . . ?
N5 Eu1 N1 110.39(6) . . ?
N6 Eu1 N1 69.74(6) . . ?
N2 Eu1 N1 62.59(6) . . ?
N3 Eu1 N1 125.45(6) . . ?
O5 Eu1 N8 25.51(5) . . ?
O4 Eu1 N8 25.60(5) . . ?
O1 Eu1 N8 152.57(5) . . ?
N4 Eu1 N8 102.94(5) . . ?
O2 Eu1 N8 155.87(5) . . ?
N5 Eu1 N8 92.11(5) . . ?
N6 Eu1 N8 72.07(5) . . ?
N2 Eu1 N8 91.30(5) . . ?
N3 Eu1 N8 69.31(5) . . ?
N1 Eu1 N8 118.34(5) . . ?
O5 Eu1 N7 153.56(5) . . ?
O4 Eu1 N7 155.18(5) . . ?
O1 Eu1 N7 25.47(5) . . ?
N4 Eu1 N7 75.01(5) . . ?
O2 Eu1 N7 25.45(5) . . ?
N5 Eu1 N7 88.55(5) . . ?
N6 Eu1 N7 110.51(5) . . ?
N2 Eu1 N7 88.32(5) . . ?
N3 Eu1 N7 108.19(5) . . ?
N1 Eu1 N7 63.76(5) . . ?
N8 Eu1 N7 177.32(5) . . ?
F6 P1 F3 177.62(17) . . ?
F6 P1 F4 90.92(13) . . ?
F3 P1 F4 89.30(15) . . ?
F6 P1 F2 91.61(15) . . ?
F3 P1 F2 90.76(19) . . ?
F4 P1 F2 91.58(13) . . ?
F6 P1 F5 88.82(14) . . ?
F3 P1 F5 88.81(18) . . ?
F4 P1 F5 90.89(13) . . ?
F2 P1 F5 177.49(13) . . ?
F6 P1 F1 89.42(12) . . ?
F3 P1 F1 90.30(14) . . ?
F4 P1 F1 178.35(12) . . ?
F2 P1 F1 90.03(12) . . ?
F5 P1 F1 87.50(11) . . ?
N7 O1 Eu1 96.08(12) . . ?
N7 O2 Eu1 95.05(11) . . ?
N8 O4 Eu1 95.23(11) . . ?
N8 O5 Eu1 96.76(11) . . ?
C5 N1 C1 117.37(19) . . ?
C5 N1 Eu1 119.02(14) . . ?
C1 N1 Eu1 120.41(15) . . ?
C6 N2 C10 118.25(19) . . ?
C6 N2 Eu1 122.10(14) . . ?
C10 N2 Eu1 118.51(14) . . ?
C11 N3 C12 118.68(19) . . ?
C11 N3 Eu1 118.95(15) . . ?
C12 N3 Eu1 121.27(14) . . ?
C15 N4 C14 118.88(19) . . ?
C15 N4 Eu1 119.28(14) . . ?
C14 N4 Eu1 120.48(14) . . ?
C20 N5 C16 118.70(18) . . ?
C20 N5 Eu1 121.67(14) . . ?
C16 N5 Eu1 118.29(14) . . ?
C25 N6 C21 118.46(19) . . ?
C25 N6 Eu1 119.87(14) . . ?
C21 N6 Eu1 121.57(14) . . ?
O3 N7 O2 121.62(18) . . ?
O3 N7 O1 121.66(18) . . ?
O2 N7 O1 116.72(17) . . ?
O3 N7 Eu1 168.71(14) . . ?
O2 N7 Eu1 59.50(10) . . ?
O1 N7 Eu1 58.45(10) . . ?
O6 N8 O5 121.73(18) . . ?
O6 N8 O4 121.39(18) . . ?
O5 N8 O4 116.88(17) . . ?
O6 N8 Eu1 177.99(15) . . ?
O5 N8 Eu1 57.73(10) . . ?
O4 N8 Eu1 59.17(10) . . ?
N1 C1 C2 123.3(2) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 118.6(2) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 119.0(2) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 118.8(2) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.8(2) . . ?
N1 C5 C6 115.44(19) . . ?
C4 C5 C6 121.7(2) . . ?
N2 C6 C7 122.4(2) . . ?
N2 C6 C5 116.00(19) . . ?
C7 C6 C5 121.6(2) . . ?
C8 C7 C6 118.8(2) . . ?
C8 C7 H7 120.6 . . ?
C6 C7 H7 120.6 . . ?
C7 C8 C9 119.2(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 118.6(2) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N2 C10 C9 122.5(2) . . ?
N2 C10 C11 115.72(19) . . ?
C9 C10 C11 121.7(2) . . ?
N3 C11 C10 120.2(2) . . ?
N3 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
N3 C12 C13 112.17(18) . . ?
N3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C27 C13 C26 109.73(19) . . ?
C27 C13 C12 107.78(18) . . ?
C26 C13 C12 110.4(2) . . ?
C27 C13 C14 109.9(2) . . ?
C26 C13 C14 107.49(18) . . ?
C12 C13 C14 111.56(18) . . ?
N4 C14 C13 114.89(17) . . ?
N4 C14 H14A 108.5 . . ?
C13 C14 H14A 108.5 . . ?
N4 C14 H14B 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
N4 C15 C16 120.7(2) . . ?
N4 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
N5 C16 C17 122.8(2) . . ?
N5 C16 C15 116.20(19) . . ?
C17 C16 C15 120.9(2) . . ?
C16 C17 C18 118.5(2) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C19 C18 C17 118.9(2) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
N5 C20 C19 121.5(2) . . ?
N5 C20 C21 115.83(18) . . ?
C19 C20 C21 122.65(19) . . ?
N6 C21 C22 121.6(2) . . ?
N6 C21 C20 116.04(18) . . ?
C22 C21 C20 122.4(2) . . ?
C21 C22 C23 119.5(2) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 118.9(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C25 C24 C23 118.7(2) . . ?
C25 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?
N6 C25 C24 122.7(2) . . ?
N6 C25 H25 118.6 . . ?
C24 C25 H25 118.6 . . ?
C13 C26 H26A 109.5 . . ?
C13 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C13 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C13 C27 H27A 109.5 . . ?
C13 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C13 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

_refine_diff_density_max         0.661
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.081

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1017809'
_audit_update_record             
;
2014-08-04 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        PrL
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H23 F6 N9 O6 P Pr'
_chemical_formula_weight         843.41

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9374(5)
_cell_length_b                   12.2439(6)
_cell_length_c                   16.3426(9)
_cell_angle_alpha                110.1560(10)
_cell_angle_beta                 105.64
_cell_angle_gamma                92.5860(10)
_cell_volume                     1597.73(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      28.05

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.753
_exptl_crystal_F_000             836
_exptl_transmission_factor_min   1.62
_exptl_transmission_factor_max   1.97
_exptl_crystal_size_max          0.470
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    1.665
_shelx_estimated_absorpt_T_min   0.508
_shelx_estimated_absorpt_T_max   0.618
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
SADABS Sheldrick 1996 
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            18146
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.793
_diffrn_reflns_theta_max         28.051
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.941
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.941
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.941
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7301
_reflns_number_gt                7111
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0437P)²+3.3770P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7301
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0819
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

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 0.93274(2) 0.83679(2) 0.69253(2) 0.01319(6) Uani 1 1 d . . . . .
N8 N 1.2008(3) 0.8644(2) 0.62071(16) 0.0179(5) Uani 1 1 d . . . . .
N7 N 0.6560(3) 0.8379(2) 0.76154(16) 0.0186(5) Uani 1 1 d . . . . .
O6 O 1.3146(3) 0.86995(19) 0.59338(16) 0.0242(4) Uani 1 1 d . . . . .
O5 O 1.2148(2) 0.90295(17) 0.70613(13) 0.0192(4) Uani 1 1 d . . . . .
O4 O 1.0632(2) 0.81971(18) 0.56606(14) 0.0203(4) Uani 1 1 d . . . . .
O1 O 0.6945(2) 0.74145(18) 0.71622(14) 0.0206(4) Uani 1 1 d . . . . .
O3 O 0.5576(3) 0.8395(2) 0.80142(15) 0.0275(5) Uani 1 1 d . . . . .
O2 O 0.7266(2) 0.93230(18) 0.76427(14) 0.0204(4) Uani 1 1 d . . . . .
N2 N 1.0662(3) 1.0382(2) 0.83110(16) 0.0178(5) Uani 1 1 d . . . . .
N5 N 0.8132(3) 0.6276(2) 0.56286(15) 0.0158(4) Uani 1 1 d . . . . .
N1 N 1.0274(3) 0.8397(2) 0.86178(16) 0.0182(5) Uani 1 1 d . . . . .
N4 N 0.7037(3) 0.8266(2) 0.55282(16) 0.0180(5) Uani 1 1 d . . . . .
N6 N 1.0864(3) 0.6558(2) 0.69208(15) 0.0162(4) Uani 1 1 d . . . . .
N3 N 0.9069(3) 1.0299(2) 0.66231(16) 0.0193(5) Uani 1 1 d . . . . .
C15 C 0.6825(3) 0.6182(2) 0.49451(18) 0.0175(5) Uani 1 1 d . . . . .
C20 C 1.0163(3) 0.5435(2) 0.64069(18) 0.0158(5) Uani 1 1 d . . . . .
C19 C 0.8640(3) 0.5286(2) 0.56932(18) 0.0161(5) Uani 1 1 d . . . . .
C16 C 0.5978(3) 0.5107(3) 0.43058(19) 0.0205(6) Uani 1 1 d . . . . .
H1 H 0.5082 0.5073 0.3821 0.025 Uiso 1 1 calc R U . . .
C11 C 0.9737(4) 1.1299(3) 0.7227(2) 0.0216(6) Uani 1 1 d . . . . .
H10 H 0.9622 1.1989 0.7089 0.026 Uiso 1 1 calc R U . . .
C10 C 1.0692(3) 1.1386(3) 0.8143(2) 0.0209(6) Uani 1 1 d . . . . .
C6 C 1.1490(3) 1.0414(3) 0.91384(19) 0.0198(5) Uani 1 1 d . . . . .
C14 C 0.6339(3) 0.7294(3) 0.48922(19) 0.0199(5) Uani 1 1 d . . . . .
H2 H 0.5507 0.7286 0.4385 0.024 Uiso 1 1 calc R U . . .
C1 C 0.9989(3) 0.7402(3) 0.8758(2) 0.0212(6) Uani 1 1 d . . . . .
H7 H 0.9261 0.6768 0.8277 0.025 Uiso 1 1 calc R U . . .
C21 C 1.0853(3) 0.4479(2) 0.6521(2) 0.0202(5) Uani 1 1 d . . . . .
H6A H 1.0334 0.3697 0.6159 0.024 Uiso 1 1 calc R U . . .
N9 N 0.2471(4) 0.1664(3) 0.6515(2) 0.0300(6) Uani 1 1 d . . . . .
C25 C 0.3448(4) 0.1503(3) 0.7059(2) 0.0249(6) Uani 1 1 d . . . . .
C26 C 0.4682(4) 0.1308(3) 0.7760(3) 0.0349(8) Uani 1 1 d . . . . .
H12A H 0.5015 0.2027 0.8311 0.052 Uiso 1 1 calc R U . . .
H12B H 0.5581 0.1101 0.7534 0.052 Uiso 1 1 calc R U . . .
H12C H 0.4282 0.0663 0.7908 0.052 Uiso 1 1 calc R U . . .
C17 C 0.6477(3) 0.4086(3) 0.4397(2) 0.0218(6) Uani 1 1 d . . . . .
H15 H 0.5908 0.3336 0.3984 0.026 Uiso 1 1 calc R U . . .
C18 C 0.7816(3) 0.4174(2) 0.5098(2) 0.0199(5) Uani 1 1 d . . . . .
H16 H 0.8170 0.3484 0.5173 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8099(4) 1.0223(3) 0.5720(2) 0.0224(6) Uani 1 1 d . . . . .
H14A H 0.8670 0.9932 0.5264 0.027 Uiso 1 1 calc R U . . .
H14B H 0.7845 1.1009 0.5741 0.027 Uiso 1 1 calc R U . . .
C13 C 0.6595(4) 0.9374(3) 0.5454(2) 0.0216(6) Uani 1 1 d . . . . .
H13A H 0.5963 0.9711 0.5868 0.026 Uiso 1 1 calc R U . . .
H13B H 0.5957 0.9234 0.4820 0.026 Uiso 1 1 calc R U . . .
C5 C 1.1298(3) 0.9309(3) 0.93068(19) 0.0190(5) Uani 1 1 d . . . . .
C4 C 1.2069(4) 0.9214(3) 1.0138(2) 0.0276(6) Uani 1 1 d . . . . .
H21 H 1.2799 0.9855 1.0611 0.033 Uiso 1 1 calc R U . . .
C2 C 1.0702(4) 0.7254(3) 0.9571(2) 0.0280(7) Uani 1 1 d . . . . .
H23 H 1.0470 0.6537 0.9647 0.034 Uiso 1 1 calc R U . . .
C8 C 1.2449(4) 1.2474(3) 0.9632(2) 0.0322(7) Uani 1 1 d . . . . .
H18 H 1.3070 1.3185 1.0081 0.039 Uiso 1 1 calc R U . . .
C7 C 1.2432(4) 1.1451(3) 0.9813(2) 0.0278(7) Uani 1 1 d . . . . .
H19 H 1.3048 1.1450 1.0386 0.033 Uiso 1 1 calc R U . . .
C9 C 1.1548(4) 1.2452(3) 0.8786(2) 0.0277(6) Uani 1 1 d . . . . .
H17 H 1.1519 1.3148 0.8652 0.033 Uiso 1 1 calc R U . . .
C3 C 1.1762(4) 0.8181(3) 1.0267(2) 0.0327(7) Uani 1 1 d . . . . .
H22 H 1.2275 0.8106 1.0832 0.039 Uiso 1 1 calc R U . . .
C24 C 1.2290(3) 0.6737(2) 0.75317(19) 0.0189(5) Uani 1 1 d . . . . .
H26 H 1.2800 0.7524 0.7881 0.023 Uiso 1 1 calc R U . . .
C23 C 1.3054(3) 0.5824(3) 0.7676(2) 0.0225(6) Uani 1 1 d . . . . .
H25 H 1.4063 0.5982 0.8113 0.027 Uiso 1 1 calc R U . . .
C22 C 1.2310(4) 0.4683(3) 0.7170(2) 0.0234(6) Uani 1 1 d . . . . .
H24 H 1.2790 0.4042 0.7265 0.028 Uiso 1 1 calc R U . . .
F6 F 0.9345(3) 0.4314(2) 0.79889(18) 0.0467(6) Uani 1 1 d . . . . .
F4 F 0.7804(3) 0.3126(2) 0.8292(2) 0.0517(7) Uani 1 1 d . . . . .
F5 F 0.5673(3) 0.3849(2) 0.7671(3) 0.0689(9) Uani 1 1 d . . . . .
F2 F 0.7278(4) 0.5003(3) 0.7332(2) 0.0670(9) Uani 1 1 d . . . . .
F3 F 0.7752(4) 0.5113(3) 0.8786(2) 0.0707(9) Uani 1 1 d . . . . .
F1 F 0.7300(4) 0.3060(3) 0.6867(2) 0.0795(10) Uani 1 1 d . . . . .
P1 P 0.75067(11) 0.40876(7) 0.78496(7) 0.03160(19) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 2.540(2) . ?
Pr1 O2 2.559(2) . ?
Pr1 O1 2.565(2) . ?
Pr1 N3 2.584(2) . ?
Pr1 N4 2.585(2) . ?
Pr1 O4 2.588(2) . ?
Pr1 N5 2.643(2) . ?
Pr1 N1 2.652(2) . ?
Pr1 N2 2.657(2) . ?
Pr1 N6 2.658(2) . ?
Pr1 N7 2.981(2) . ?
Pr1 N8 2.991(2) . ?
N8 O6 1.224(3) . ?
N8 O4 1.273(3) . ?
N8 O5 1.278(3) . ?
N7 O3 1.224(3) . ?
N7 O2 1.273(3) . ?
N7 O1 1.278(3) . ?
N2 C6 1.341(4) . ?
N2 C10 1.350(4) . ?
N5 C19 1.341(4) . ?
N5 C15 1.350(4) . ?
N1 C1 1.340(4) . ?
N1 C5 1.356(4) . ?
N4 C14 1.271(4) . ?
N4 C13 1.465(4) . ?
N6 C24 1.344(4) . ?
N6 C20 1.353(3) . ?
N3 C11 1.270(4) . ?
N3 C12 1.466(4) . ?
C15 C16 1.390(4) . ?
C15 C14 1.471(4) . ?
C20 C21 1.392(4) . ?
C20 C19 1.490(4) . ?
C19 C18 1.398(4) . ?
C16 C17 1.389(4) . ?
C16 H1 0.9500 . ?
C11 C10 1.473(4) . ?
C11 H10 0.9500 . ?
C10 C9 1.387(4) . ?
C6 C7 1.405(4) . ?
C6 C5 1.483(4) . ?
C14 H2 0.9500 . ?
C1 C2 1.387(4) . ?
C1 H7 0.9500 . ?
C21 C22 1.388(4) . ?
C21 H6A 0.9500 . ?
N9 C25 1.144(4) . ?
C25 C26 1.455(5) . ?
C26 H12A 0.9800 . ?
C26 H12B 0.9800 . ?
C26 H12C 0.9800 . ?
C17 C18 1.385(4) . ?
C17 H15 0.9500 . ?
C18 H16 0.9500 . ?
C12 C13 1.525(4) . ?
C12 H14A 0.9900 . ?
C12 H14B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C5 C4 1.395(4) . ?
C4 C3 1.380(5) . ?
C4 H21 0.9500 . ?
C2 C3 1.382(5) . ?
C2 H23 0.9500 . ?
C8 C7 1.383(5) . ?
C8 C9 1.390(5) . ?
C8 H18 0.9500 . ?
C7 H19 0.9500 . ?
C9 H17 0.9500 . ?
C3 H22 0.9500 . ?
C24 C23 1.392(4) . ?
C24 H26 0.9500 . ?
C23 C22 1.379(4) . ?
C23 H25 0.9500 . ?
C22 H24 0.9500 . ?
F6 P1 1.594(3) . ?
F4 P1 1.578(2) . ?
F5 P1 1.580(3) . ?
F2 P1 1.611(3) . ?
F3 P1 1.561(3) . ?
F1 P1 1.619(3) . ?

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 135.11(6) . . ?
O5 Pr1 O1 161.33(7) . . ?
O2 Pr1 O1 50.13(6) . . ?
O5 Pr1 N3 78.85(7) . . ?
O2 Pr1 N3 73.39(7) . . ?
O1 Pr1 N3 117.08(7) . . ?
O5 Pr1 N4 120.79(7) . . ?
O2 Pr1 N4 76.62(7) . . ?
O1 Pr1 N4 76.89(7) . . ?
N3 Pr1 N4 63.84(8) . . ?
O5 Pr1 O4 50.06(6) . . ?
O2 Pr1 O4 144.20(7) . . ?
O1 Pr1 O4 140.32(6) . . ?
N3 Pr1 O4 74.34(7) . . ?
N4 Pr1 O4 75.56(7) . . ?
O5 Pr1 N5 112.94(7) . . ?
O2 Pr1 N5 111.65(7) . . ?
O1 Pr1 N5 68.13(7) . . ?
N3 Pr1 N5 122.39(7) . . ?
N4 Pr1 N5 62.35(7) . . ?
O4 Pr1 N5 73.96(7) . . ?
O5 Pr1 N1 89.69(7) . . ?
O2 Pr1 N1 75.84(7) . . ?
O1 Pr1 N1 73.94(7) . . ?
N3 Pr1 N1 120.99(7) . . ?
N4 Pr1 N1 148.57(8) . . ?
O4 Pr1 N1 135.60(7) . . ?
N5 Pr1 N1 115.44(7) . . ?
O5 Pr1 N2 65.93(7) . . ?
O2 Pr1 N2 70.04(7) . . ?
O1 Pr1 N2 111.39(7) . . ?
N3 Pr1 N2 62.14(8) . . ?
N4 Pr1 N2 122.25(7) . . ?
O4 Pr1 N2 107.35(7) . . ?
N5 Pr1 N2 175.34(7) . . ?
N1 Pr1 N2 60.41(7) . . ?
O5 Pr1 N6 73.10(7) . . ?
O2 Pr1 N6 136.40(7) . . ?
O1 Pr1 N6 92.83(7) . . ?
N3 Pr1 N6 149.36(8) . . ?
N4 Pr1 N6 121.77(7) . . ?
O4 Pr1 N6 78.27(7) . . ?
N5 Pr1 N6 60.74(7) . . ?
N1 Pr1 N6 71.52(7) . . ?
N2 Pr1 N6 114.92(7) . . ?
O5 Pr1 N7 154.25(6) . . ?
O2 Pr1 N7 25.11(7) . . ?
O1 Pr1 N7 25.24(7) . . ?
N3 Pr1 N7 96.45(7) . . ?
N4 Pr1 N7 77.75(7) . . ?
O4 Pr1 N7 153.15(6) . . ?
N5 Pr1 N7 91.10(7) . . ?
N1 Pr1 N7 70.88(7) . . ?
N2 Pr1 N7 89.35(7) . . ?
N6 Pr1 N7 114.18(7) . . ?
O5 Pr1 N8 25.05(6) . . ?
O2 Pr1 N8 148.06(6) . . ?
O1 Pr1 N8 160.51(6) . . ?
N3 Pr1 N8 76.29(7) . . ?
N4 Pr1 N8 98.79(7) . . ?
O4 Pr1 N8 25.05(7) . . ?
N5 Pr1 N8 92.91(7) . . ?
N1 Pr1 N8 112.60(7) . . ?
N2 Pr1 N8 87.14(7) . . ?
N6 Pr1 N8 73.08(7) . . ?
N7 Pr1 N8 172.74(7) . . ?
O6 N8 O4 122.0(2) . . ?
O6 N8 O5 121.4(2) . . ?
O4 N8 O5 116.6(2) . . ?
O6 N8 Pr1 175.68(19) . . ?
O4 N8 Pr1 59.46(13) . . ?
O5 N8 Pr1 57.30(13) . . ?
O3 N7 O2 121.7(2) . . ?
O3 N7 O1 121.7(2) . . ?
O2 N7 O1 116.7(2) . . ?
O3 N7 Pr1 170.79(19) . . ?
O2 N7 Pr1 58.57(13) . . ?
O1 N7 Pr1 58.85(13) . . ?
N8 O5 Pr1 97.65(15) . . ?
N8 O4 Pr1 95.48(15) . . ?
N7 O1 Pr1 95.91(15) . . ?
N7 O2 Pr1 96.32(15) . . ?
C6 N2 C10 118.7(2) . . ?
C6 N2 Pr1 122.06(19) . . ?
C10 N2 Pr1 118.62(18) . . ?
C19 N5 C15 118.5(2) . . ?
C19 N5 Pr1 122.19(17) . . ?
C15 N5 Pr1 118.64(18) . . ?
C1 N1 C5 118.5(2) . . ?
C1 N1 Pr1 118.88(18) . . ?
C5 N1 Pr1 121.30(18) . . ?
C14 N4 C13 119.6(2) . . ?
C14 N4 Pr1 122.13(19) . . ?
C13 N4 Pr1 118.20(17) . . ?
C24 N6 C20 118.2(2) . . ?
C24 N6 Pr1 119.62(18) . . ?
C20 N6 Pr1 121.51(17) . . ?
C11 N3 C12 119.4(2) . . ?
C11 N3 Pr1 122.5(2) . . ?
C12 N3 Pr1 118.06(17) . . ?
N5 C15 C16 123.1(3) . . ?
N5 C15 C14 116.3(2) . . ?
C16 C15 C14 120.6(3) . . ?
N6 C20 C21 121.8(3) . . ?
N6 C20 C19 116.0(2) . . ?
C21 C20 C19 122.2(2) . . ?
N5 C19 C18 121.7(3) . . ?
N5 C19 C20 116.4(2) . . ?
C18 C19 C20 121.9(3) . . ?
C17 C16 C15 118.1(3) . . ?
C17 C16 H1 120.9 . . ?
C15 C16 H1 120.9 . . ?
N3 C11 C10 119.9(3) . . ?
N3 C11 H10 120.1 . . ?
C10 C11 H10 120.1 . . ?
N2 C10 C9 123.0(3) . . ?
N2 C10 C11 116.1(3) . . ?
C9 C10 C11 120.9(3) . . ?
N2 C6 C7 121.6(3) . . ?
N2 C6 C5 116.0(2) . . ?
C7 C6 C5 122.4(3) . . ?
N4 C14 C15 119.7(3) . . ?
N4 C14 H2 120.1 . . ?
C15 C14 H2 120.1 . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H7 118.4 . . ?
C2 C1 H7 118.4 . . ?
C22 C21 C20 119.1(3) . . ?
C22 C21 H6A 120.5 . . ?
C20 C21 H6A 120.4 . . ?
N9 C25 C26 179.3(4) . . ?
C25 C26 H12A 109.5 . . ?
C25 C26 H12B 109.5 . . ?
H12A C26 H12B 109.5 . . ?
C25 C26 H12C 109.5 . . ?
H12A C26 H12C 109.5 . . ?
H12B C26 H12C 109.5 . . ?
C18 C17 C16 119.2(3) . . ?
C18 C17 H15 120.4 . . ?
C16 C17 H15 120.4 . . ?
C17 C18 C19 119.4(3) . . ?
C17 C18 H16 120.3 . . ?
C19 C18 H16 120.3 . . ?
N3 C12 C13 107.6(2) . . ?
N3 C12 H14A 110.2 . . ?
C13 C12 H14A 110.2 . . ?
N3 C12 H14B 110.2 . . ?
C13 C12 H14B 110.2 . . ?
H14A C12 H14B 108.5 . . ?
N4 C13 C12 108.1(2) . . ?
N4 C13 H13A 110.1 . . ?
C12 C13 H13A 110.1 . . ?
N4 C13 H13B 110.1 . . ?
C12 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
N1 C5 C4 121.2(3) . . ?
N1 C5 C6 116.3(2) . . ?
C4 C5 C6 122.5(3) . . ?
C3 C4 C5 119.4(3) . . ?
C3 C4 H21 120.3 . . ?
C5 C4 H21 120.3 . . ?
C3 C2 C1 118.1(3) . . ?
C3 C2 H23 121.0 . . ?
C1 C2 H23 121.0 . . ?
C7 C8 C9 119.4(3) . . ?
C7 C8 H18 120.3 . . ?
C9 C8 H18 120.3 . . ?
C8 C7 C6 119.1(3) . . ?
C8 C7 H19 120.5 . . ?
C6 C7 H19 120.5 . . ?
C10 C9 C8 118.2(3) . . ?
C10 C9 H17 120.9 . . ?
C8 C9 H17 120.9 . . ?
C4 C3 C2 119.6(3) . . ?
C4 C3 H22 120.2 . . ?
C2 C3 H22 120.2 . . ?
N6 C24 C23 123.0(3) . . ?
N6 C24 H26 118.5 . . ?
C23 C24 H26 118.5 . . ?
C22 C23 C24 118.4(3) . . ?
C22 C23 H25 120.8 . . ?
C24 C23 H25 120.8 . . ?
C23 C22 C21 119.4(3) . . ?
C23 C22 H24 120.3 . . ?
C21 C22 H24 120.3 . . ?
F3 P1 F4 93.75(19) . . ?
F3 P1 F5 92.41(18) . . ?
F4 P1 F5 92.11(15) . . ?
F3 P1 F6 89.44(16) . . ?
F4 P1 F6 88.97(13) . . ?
F5 P1 F6 177.79(18) . . ?
F3 P1 F2 90.54(19) . . ?
F4 P1 F2 174.81(19) . . ?
F5 P1 F2 90.62(16) . . ?
F6 P1 F2 88.16(15) . . ?
F3 P1 F1 177.5(2) . . ?
F4 P1 F1 87.99(18) . . ?
F5 P1 F1 89.3(2) . . ?
F6 P1 F1 88.83(18) . . ?
F2 P1 F1 87.63(19) . . ?

_refine_diff_density_max         3.307
_refine_diff_density_min         -1.227
_refine_diff_density_rms         0.114

_shelxl_version_number           2013-4


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC4
_audit_block_doi                 10.5517/cc140wrs
_database_code_depnum_ccdc_archive 'CCDC 1043545'
_audit_update_record             
;
2015-01-14 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        PrL3
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H29 F6 N9 O6 P Pr'
_chemical_formula_weight         885.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.2569(6)
_cell_length_b                   12.6567(7)
_cell_length_c                   13.6840(8)
_cell_angle_alpha                63.8810(10)
_cell_angle_beta                 88.0730(10)
_cell_angle_gamma                85.0690(10)
_cell_volume                     1744.04(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9947
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.54

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.686
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   1.38
_exptl_transmission_factor_max   1.67
_exptl_crystal_size_max          0.376
_exptl_crystal_size_mid          0.238
_exptl_crystal_size_min          0.227
_exptl_absorpt_coefficient_mu    1.530
_shelx_estimated_absorpt_T_min   0.597
_shelx_estimated_absorpt_T_max   0.723
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
SADABS Sheldrick 1996 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19805
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.657
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7846
_reflns_number_gt                7411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+2.8898P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7846
_refine_ls_number_parameters     472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0294
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0696
_refine_ls_wR_factor_gt          0.0683
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.23008(2) 0.21132(2) 0.49492(2) 0.01256(5) Uani 1 1 d . . . . .
P1 P 0.26105(7) 0.24579(7) 0.94210(6) 0.02786(16) Uani 1 1 d . . . . .
O6 O 0.12785(17) 0.53159(16) 0.50981(17) 0.0244(4) Uani 1 1 d . . . . .
N5 N 0.38972(18) 0.32133(18) 0.34462(17) 0.0161(4) Uani 1 1 d . . . . .
O3 O 0.32571(18) -0.10466(17) 0.46931(19) 0.0299(5) Uani 1 1 d . . . . .
N2 N 0.07779(18) 0.10638(18) 0.65395(17) 0.0156(4) Uani 1 1 d . . . . .
N7 N 0.29544(19) -0.01103(18) 0.47240(17) 0.0178(4) Uani 1 1 d . . . . .
O5 O 0.14866(16) 0.33918(16) 0.58827(14) 0.0196(4) Uani 1 1 d . . . . .
O4 O 0.18838(16) 0.43528(15) 0.41681(14) 0.0188(4) Uani 1 1 d . . . . .
N8 N 0.15387(18) 0.43756(18) 0.50564(18) 0.0173(4) Uani 1 1 d . . . . .
O1 O 0.18954(15) 0.01228(15) 0.49722(14) 0.0182(3) Uani 1 1 d . . . . .
O2 O 0.36829(15) 0.06780(15) 0.45097(15) 0.0188(4) Uani 1 1 d . . . . .
N6 N 0.41374(18) 0.29602(18) 0.54872(17) 0.0170(4) Uani 1 1 d . . . . .
N4 N 0.18517(18) 0.25085(18) 0.29518(17) 0.0163(4) Uani 1 1 d . . . . .
N3 N 0.00293(18) 0.25684(18) 0.44746(17) 0.0156(4) Uani 1 1 d . . . . .
F4 F 0.28314(16) 0.14792(17) 1.06536(14) 0.0356(4) Uani 1 1 d . . . . .
F2 F 0.2390(2) 0.34577(19) 0.82015(14) 0.0447(5) Uani 1 1 d . . . . .
N1 N 0.31185(19) 0.04609(18) 0.68174(17) 0.0186(4) Uani 1 1 d . . . . .
C25 C 0.4235(2) 0.2834(2) 0.6509(2) 0.0201(5) Uani 1 1 d . . . . .
H25 H 0.3604 0.2507 0.7001 0.024 Uiso 1 1 calc R U . . .
F1 F 0.1894(2) 0.15731(18) 0.91774(18) 0.0529(6) Uani 1 1 d . . . . .
C11 C -0.0750(2) 0.2176(2) 0.5216(2) 0.0173(5) Uani 1 1 d . . . . .
H11 H -0.1569 0.2411 0.5040 0.021 Uiso 1 1 calc R U . . .
C13 C -0.0319(2) 0.3011(2) 0.2512(2) 0.0173(5) Uani 1 1 d . . . . .
C21 C 0.5027(2) 0.3456(2) 0.4784(2) 0.0164(5) Uani 1 1 d . . . . .
C14 C 0.0771(2) 0.2121(2) 0.2681(2) 0.0168(5) Uani 1 1 d . . . . .
H14A H 0.0601 0.1346 0.3275 0.020 Uiso 1 1 calc R U . . .
H14B H 0.0910 0.2019 0.2008 0.020 Uiso 1 1 calc R U . . .
F6 F 0.1411(2) 0.2909(2) 0.97928(17) 0.0580(7) Uani 1 1 d . . . . .
C22 C 0.6031(2) 0.3796(2) 0.5105(2) 0.0194(5) Uani 1 1 d . . . . .
H22 H 0.6648 0.4134 0.4599 0.023 Uiso 1 1 calc R U . . .
C12 C -0.0364(2) 0.3466(2) 0.3389(2) 0.0177(5) Uani 1 1 d . . . . .
H12A H 0.0146 0.4134 0.3156 0.021 Uiso 1 1 calc R U . . .
H12B H -0.1192 0.3770 0.3441 0.021 Uiso 1 1 calc R U . . .
C10 C -0.0400(2) 0.1363(2) 0.6345(2) 0.0171(5) Uani 1 1 d . . . . .
F5 F 0.3802(2) 0.1927(3) 0.90719(19) 0.0799(10) Uani 1 1 d . . . . .
C15 C 0.2625(2) 0.2933(2) 0.2214(2) 0.0197(5) Uani 1 1 d . . . . .
H15 H 0.2491 0.2981 0.1513 0.024 Uiso 1 1 calc R U . . .
C16 C 0.3726(2) 0.3351(2) 0.2422(2) 0.0187(5) Uani 1 1 d . . . . .
C17 C 0.4517(2) 0.3878(3) 0.1580(2) 0.0247(6) Uani 1 1 d . . . . .
H17 H 0.4380 0.3938 0.0876 0.030 Uiso 1 1 calc R U . . .
C5 C 0.2443(2) 0.0023(2) 0.7723(2) 0.0198(5) Uani 1 1 d . . . . .
C9 C -0.1253(2) 0.0985(2) 0.7156(2) 0.0220(5) Uani 1 1 d . . . . .
H9 H -0.2077 0.1201 0.6989 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4872(2) 0.3624(2) 0.3649(2) 0.0165(5) Uani 1 1 d . . . . .
C23 C 0.6121(2) 0.3638(2) 0.6171(2) 0.0215(5) Uani 1 1 d . . . . .
H23 H 0.6803 0.3859 0.6406 0.026 Uiso 1 1 calc R U . . .
C19 C 0.5690(2) 0.4200(2) 0.2830(2) 0.0218(5) Uani 1 1 d . . . . .
H19 H 0.6360 0.4508 0.2987 0.026 Uiso 1 1 calc R U . . .
C24 C 0.5205(2) 0.3153(2) 0.6886(2) 0.0216(5) Uani 1 1 d . . . . .
H24 H 0.5240 0.3042 0.7619 0.026 Uiso 1 1 calc R U . . .
C1 C 0.4287(2) 0.0119(2) 0.6904(2) 0.0243(5) Uani 1 1 d . . . . .
H1 H 0.4761 0.0410 0.6265 0.029 Uiso 1 1 calc R U . . .
C2 C 0.4834(3) -0.0643(3) 0.7886(3) 0.0335(7) Uani 1 1 d . . . . .
H2 H 0.5663 -0.0874 0.7919 0.040 Uiso 1 1 calc R U . . .
C26 C -0.1431(2) 0.2375(2) 0.2566(2) 0.0227(5) Uani 1 1 d . . . . .
H26A H -0.2142 0.2921 0.2446 0.034 Uiso 1 1 calc R U . . .
H26B H -0.1476 0.1701 0.3284 0.034 Uiso 1 1 calc R U . . .
H26C H -0.1388 0.2093 0.2003 0.034 Uiso 1 1 calc R U . . .
C6 C 0.1141(2) 0.0367(2) 0.7568(2) 0.0187(5) Uani 1 1 d . . . . .
C27 C -0.0258(3) 0.4077(2) 0.1404(2) 0.0251(6) Uani 1 1 d . . . . .
H27A H -0.0299 0.3821 0.0827 0.038 Uiso 1 1 calc R U . . .
H27B H 0.0493 0.4437 0.1346 0.038 Uiso 1 1 calc R U . . .
H27C H -0.0929 0.4655 0.1327 0.038 Uiso 1 1 calc R U . . .
C7 C 0.0329(3) -0.0029(2) 0.8430(2) 0.0240(5) Uani 1 1 d . . . . .
H7 H 0.0604 -0.0508 0.9153 0.029 Uiso 1 1 calc R U . . .
C8 C -0.0872(3) 0.0283(2) 0.8220(2) 0.0250(6) Uani 1 1 d . . . . .
H8 H -0.1433 0.0020 0.8796 0.030 Uiso 1 1 calc R U . . .
C18 C 0.5514(2) 0.4317(3) 0.1791(2) 0.0259(6) Uani 1 1 d . . . . .
H18 H 0.6068 0.4692 0.1230 0.031 Uiso 1 1 calc R U . . .
C28 C 0.0424(3) 0.6710(3) 0.2236(3) 0.0344(7) Uani 1 1 d . . . . .
H28A H -0.0005 0.7486 0.2030 0.052 Uiso 1 1 calc R U . . .
H28B H 0.0573 0.6326 0.3022 0.052 Uiso 1 1 calc R U . . .
H28C H -0.0057 0.6221 0.2042 0.052 Uiso 1 1 calc R U . . .
F3 F 0.3350(3) 0.3303(3) 0.96917(19) 0.1014(14) Uani 1 1 d . . . . .
C4 C 0.2936(3) -0.0734(3) 0.8735(2) 0.0341(7) Uani 1 1 d . . . . .
H4 H 0.2447 -0.1025 0.9364 0.041 Uiso 1 1 calc R U . . .
C3 C 0.4147(3) -0.1059(3) 0.8814(3) 0.0408(8) Uani 1 1 d . . . . .
H3 H 0.4503 -0.1563 0.9501 0.049 Uiso 1 1 calc R U . . .
C29 C 0.1540(4) 0.6854(4) 0.1668(3) 0.0544(10) Uani 1 1 d . . . . .
N9 N 0.2432(5) 0.6986(6) 0.1230(4) 0.112(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

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 O2 2.5485(17) . ?
Pr1 O4 2.5564(17) . ?
Pr1 O5 2.5646(18) . ?
Pr1 O1 2.5850(17) . ?
Pr1 N3 2.612(2) . ?
Pr1 N4 2.612(2) . ?
Pr1 N1 2.622(2) . ?
Pr1 N2 2.652(2) . ?
Pr1 N5 2.657(2) . ?
Pr1 N6 2.673(2) . ?
Pr1 N7 2.991(2) . ?
Pr1 N8 2.983(2) . ?
P1 F6 1.576(2) . ?
P1 F3 1.581(2) . ?
P1 F1 1.587(2) . ?
P1 F2 1.601(2) . ?
P1 F4 1.6052(19) . ?
P1 F5 1.601(3) . ?
O6 N8 1.226(3) . ?
N5 C20 1.340(3) . ?
N5 C16 1.352(3) . ?
O3 N7 1.223(3) . ?
N2 C10 1.350(3) . ?
N2 C6 1.345(3) . ?
N7 O2 1.273(3) . ?
N7 O1 1.274(3) . ?
O5 N8 1.265(3) . ?
O4 N8 1.275(3) . ?
N6 C21 1.354(3) . ?
N6 C25 1.343(3) . ?
N4 C15 1.269(3) . ?
N4 C14 1.466(3) . ?
N3 C11 1.272(3) . ?
N3 C12 1.471(3) . ?
N1 C1 1.341(3) . ?
N1 C5 1.352(3) . ?
C25 C24 1.386(4) . ?
C25 H25 0.9500 . ?
C11 C10 1.474(4) . ?
C11 H11 0.9500 . ?
C13 C26 1.529(3) . ?
C13 C27 1.527(3) . ?
C13 C12 1.540(3) . ?
C13 C14 1.543(3) . ?
C21 C22 1.393(3) . ?
C21 C20 1.487(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C22 C23 1.388(4) . ?
C22 H22 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C10 C9 1.387(3) . ?
C15 C16 1.472(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C17 C18 1.385(4) . ?
C17 H17 0.9500 . ?
C5 C4 1.391(4) . ?
C5 C6 1.488(4) . ?
C9 C8 1.390(4) . ?
C9 H9 0.9500 . ?
C20 C19 1.401(3) . ?
C23 C24 1.382(4) . ?
C23 H23 0.9500 . ?
C19 C18 1.383(4) . ?
C19 H19 0.9500 . ?
C24 H24 0.9500 . ?
C1 C2 1.389(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(5) . ?
C2 H2 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C6 C7 1.402(4) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C7 C8 1.379(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C18 H18 0.9500 . ?
C28 C29 1.437(5) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C4 C3 1.384(5) . ?
C4 H4 0.9500 . ?
C3 H3 0.9500 . ?
C29 N9 1.138(6) . ?

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
O2 Pr1 O4 136.51(6) . . ?
O2 Pr1 O5 159.93(6) . . ?
O4 Pr1 O5 50.06(6) . . ?
O2 Pr1 O1 50.01(5) . . ?
O4 Pr1 O1 150.11(6) . . ?
O5 Pr1 O1 137.63(6) . . ?
O2 Pr1 N3 124.53(6) . . ?
O4 Pr1 N3 73.45(6) . . ?
O5 Pr1 N3 74.26(6) . . ?
O1 Pr1 N3 81.81(6) . . ?
O2 Pr1 N4 72.38(6) . . ?
O4 Pr1 N4 82.70(6) . . ?
O5 Pr1 N4 125.94(6) . . ?
O1 Pr1 N4 72.29(6) . . ?
N3 Pr1 N4 67.31(6) . . ?
O2 Pr1 N1 73.53(6) . . ?
O4 Pr1 N1 134.31(6) . . ?
O5 Pr1 N1 90.54(6) . . ?
O1 Pr1 N1 73.65(6) . . ?
N3 Pr1 N1 122.77(7) . . ?
N4 Pr1 N1 142.28(6) . . ?
O2 Pr1 N2 113.67(6) . . ?
O4 Pr1 N2 109.67(6) . . ?
O5 Pr1 N2 66.33(6) . . ?
O1 Pr1 N2 71.70(6) . . ?
N3 Pr1 N2 62.54(6) . . ?
N4 Pr1 N2 120.96(6) . . ?
N1 Pr1 N2 60.85(6) . . ?
O2 Pr1 N5 67.95(6) . . ?
O4 Pr1 N5 69.04(6) . . ?
O5 Pr1 N5 110.83(6) . . ?
O1 Pr1 N5 111.37(6) . . ?
N3 Pr1 N5 119.87(6) . . ?
N4 Pr1 N5 62.84(6) . . ?
N1 Pr1 N5 117.13(6) . . ?
N2 Pr1 N5 176.05(6) . . ?
O2 Pr1 N6 91.93(6) . . ?
O4 Pr1 N6 72.36(6) . . ?
O5 Pr1 N6 71.48(6) . . ?
O1 Pr1 N6 135.43(6) . . ?
N3 Pr1 N6 142.10(6) . . ?
N4 Pr1 N6 123.07(6) . . ?
N1 Pr1 N6 73.54(6) . . ?
N2 Pr1 N6 115.53(6) . . ?
N5 Pr1 N6 60.57(6) . . ?
O2 Pr1 N7 24.97(5) . . ?
O4 Pr1 N7 152.48(6) . . ?
O5 Pr1 N7 156.95(6) . . ?
O1 Pr1 N7 25.09(5) . . ?
N3 Pr1 N7 104.16(6) . . ?
N4 Pr1 N7 71.55(6) . . ?
N1 Pr1 N7 70.72(6) . . ?
N2 Pr1 N7 92.22(6) . . ?
N5 Pr1 N7 90.14(6) . . ?
N6 Pr1 N7 113.72(6) . . ?
O2 Pr1 N8 156.26(6) . . ?
O4 Pr1 N8 25.14(6) . . ?
O5 Pr1 N8 24.94(6) . . ?
O1 Pr1 N8 153.01(5) . . ?
N3 Pr1 N8 72.82(6) . . ?
N4 Pr1 N8 105.13(6) . . ?
N1 Pr1 N8 112.58(6) . . ?
N2 Pr1 N8 88.20(6) . . ?
N5 Pr1 N8 89.65(6) . . ?
N6 Pr1 N8 69.28(6) . . ?
N7 Pr1 N8 176.33(6) . . ?
F6 P1 F3 91.80(19) . . ?
F6 P1 F1 89.15(14) . . ?
F3 P1 F1 178.11(17) . . ?
F6 P1 F2 90.34(12) . . ?
F3 P1 F2 90.73(13) . . ?
F1 P1 F2 90.89(11) . . ?
F6 P1 F4 88.97(11) . . ?
F3 P1 F4 88.12(12) . . ?
F1 P1 F4 90.27(11) . . ?
F2 P1 F4 178.64(12) . . ?
F6 P1 F5 176.78(17) . . ?
F3 P1 F5 90.8(2) . . ?
F1 P1 F5 88.21(16) . . ?
F2 P1 F5 91.55(13) . . ?
F4 P1 F5 89.19(12) . . ?
C20 N5 C16 118.2(2) . . ?
C20 N5 Pr1 123.70(16) . . ?
C16 N5 Pr1 118.14(16) . . ?
C10 N2 C6 118.4(2) . . ?
C10 N2 Pr1 118.79(16) . . ?
C6 N2 Pr1 122.15(16) . . ?
O3 N7 O2 121.6(2) . . ?
O3 N7 O1 121.6(2) . . ?
O2 N7 O1 116.82(19) . . ?
O3 N7 Pr1 176.02(18) . . ?
O2 N7 Pr1 57.66(11) . . ?
O1 N7 Pr1 59.32(11) . . ?
N8 O5 Pr1 96.35(13) . . ?
N8 O4 Pr1 96.47(13) . . ?
O6 N8 O5 122.1(2) . . ?
O6 N8 O4 120.8(2) . . ?
O5 N8 O4 117.04(19) . . ?
O6 N8 Pr1 177.11(16) . . ?
O5 N8 Pr1 58.71(11) . . ?
O4 N8 Pr1 58.39(11) . . ?
N7 O1 Pr1 95.59(13) . . ?
N7 O2 Pr1 97.37(13) . . ?
C21 N6 C25 117.7(2) . . ?
C21 N6 Pr1 122.54(16) . . ?
C25 N6 Pr1 119.64(16) . . ?
C15 N4 C14 118.2(2) . . ?
C15 N4 Pr1 120.29(17) . . ?
C14 N4 Pr1 121.09(15) . . ?
C11 N3 C12 118.4(2) . . ?
C11 N3 Pr1 120.67(16) . . ?
C12 N3 Pr1 119.89(15) . . ?
C1 N1 C5 118.4(2) . . ?
C1 N1 Pr1 118.31(17) . . ?
C5 N1 Pr1 122.97(16) . . ?
N6 C25 C24 123.7(2) . . ?
N6 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
N3 C11 C10 121.0(2) . . ?
N3 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C26 C13 C27 109.7(2) . . ?
C26 C13 C12 110.6(2) . . ?
C27 C13 C12 107.8(2) . . ?
C26 C13 C14 107.3(2) . . ?
C27 C13 C14 110.4(2) . . ?
C12 C13 C14 111.08(19) . . ?
N6 C21 C22 121.9(2) . . ?
N6 C21 C20 116.4(2) . . ?
C22 C21 C20 121.7(2) . . ?
N4 C14 C13 112.09(19) . . ?
N4 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N4 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C23 C22 C21 119.3(2) . . ?
C23 C22 H22 120.3 . . ?
C21 C22 H22 120.3 . . ?
N3 C12 C13 114.1(2) . . ?
N3 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
N3 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
N2 C10 C9 123.1(2) . . ?
N2 C10 C11 116.5(2) . . ?
C9 C10 C11 120.4(2) . . ?
N4 C15 C16 121.3(2) . . ?
N4 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
N5 C16 C17 123.2(2) . . ?
N5 C16 C15 116.9(2) . . ?
C17 C16 C15 119.8(2) . . ?
C18 C17 C16 118.3(2) . . ?
C18 C17 H17 120.8 . . ?
C16 C17 H17 120.8 . . ?
N1 C5 C4 121.7(3) . . ?
N1 C5 C6 116.1(2) . . ?
C4 C5 C6 122.1(3) . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N5 C20 C19 121.7(2) . . ?
N5 C20 C21 116.5(2) . . ?
C19 C20 C21 121.8(2) . . ?
C24 C23 C22 119.0(2) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C18 C19 C20 119.4(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C23 C24 C25 118.4(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
N1 C1 C2 122.8(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C13 C26 H26A 109.5 . . ?
C13 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C13 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N2 C6 C7 121.5(2) . . ?
N2 C6 C5 116.0(2) . . ?
C7 C6 C5 122.5(2) . . ?
C13 C27 H27A 109.5 . . ?
C13 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C13 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C8 C7 C6 119.4(3) . . ?
C8 C7 H7 120.3 . . ?
C6 C7 H7 120.3 . . ?
C7 C8 C9 119.3(2) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C19 C18 C17 119.1(2) . . ?
C19 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
C29 C28 H28A 109.5 . . ?
C29 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C29 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C3 C4 C5 119.2(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
N9 C29 C28 178.2(6) . . ?

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 O5 N8 O6 -176.74(19) . . . . ?
Pr1 O5 N8 O4 2.8(2) . . . . ?
Pr1 O4 N8 O6 176.74(18) . . . . ?
Pr1 O4 N8 O5 -2.8(2) . . . . ?
O3 N7 O1 Pr1 175.5(2) . . . . ?
O2 N7 O1 Pr1 -4.5(2) . . . . ?
O3 N7 O2 Pr1 -175.4(2) . . . . ?
O1 N7 O2 Pr1 4.6(2) . . . . ?
C21 N6 C25 C24 -1.8(4) . . . . ?
Pr1 N6 C25 C24 174.3(2) . . . . ?
C12 N3 C11 C10 -174.1(2) . . . . ?
Pr1 N3 C11 C10 -5.9(3) . . . . ?
C25 N6 C21 C22 1.9(4) . . . . ?
Pr1 N6 C21 C22 -174.06(17) . . . . ?
C25 N6 C21 C20 -177.9(2) . . . . ?
Pr1 N6 C21 C20 6.2(3) . . . . ?
C15 N4 C14 C13 -103.6(3) . . . . ?
Pr1 N4 C14 C13 83.6(2) . . . . ?
C26 C13 C14 N4 -163.9(2) . . . . ?
C27 C13 C14 N4 76.6(3) . . . . ?
C12 C13 C14 N4 -42.9(3) . . . . ?
N6 C21 C22 C23 -0.8(4) . . . . ?
C20 C21 C22 C23 178.9(2) . . . . ?
C11 N3 C12 C13 -109.0(3) . . . . ?
Pr1 N3 C12 C13 82.6(2) . . . . ?
C26 C13 C12 N3 82.2(3) . . . . ?
C27 C13 C12 N3 -157.9(2) . . . . ?
C14 C13 C12 N3 -36.8(3) . . . . ?
C6 N2 C10 C9 0.1(4) . . . . ?
Pr1 N2 C10 C9 -171.14(19) . . . . ?
C6 N2 C10 C11 177.0(2) . . . . ?
Pr1 N2 C10 C11 5.8(3) . . . . ?
N3 C11 C10 N2 0.0(3) . . . . ?
N3 C11 C10 C9 176.9(2) . . . . ?
C14 N4 C15 C16 179.4(2) . . . . ?
Pr1 N4 C15 C16 -7.7(3) . . . . ?
C20 N5 C16 C17 1.0(4) . . . . ?
Pr1 N5 C16 C17 -178.0(2) . . . . ?
C20 N5 C16 C15 -177.7(2) . . . . ?
Pr1 N5 C16 C15 3.3(3) . . . . ?
N4 C15 C16 N5 2.9(4) . . . . ?
N4 C15 C16 C17 -175.9(3) . . . . ?
N5 C16 C17 C18 -2.0(4) . . . . ?
C15 C16 C17 C18 176.7(3) . . . . ?
C1 N1 C5 C4 2.1(4) . . . . ?
Pr1 N1 C5 C4 -171.2(2) . . . . ?
C1 N1 C5 C6 -175.9(2) . . . . ?
Pr1 N1 C5 C6 10.8(3) . . . . ?
N2 C10 C9 C8 1.1(4) . . . . ?
C11 C10 C9 C8 -175.7(2) . . . . ?
C16 N5 C20 C19 1.1(4) . . . . ?
Pr1 N5 C20 C19 -179.96(18) . . . . ?
C16 N5 C20 C21 179.9(2) . . . . ?
Pr1 N5 C20 C21 -1.1(3) . . . . ?
N6 C21 C20 N5 -3.3(3) . . . . ?
C22 C21 C20 N5 177.0(2) . . . . ?
N6 C21 C20 C19 175.6(2) . . . . ?
C22 C21 C20 C19 -4.2(4) . . . . ?
C21 C22 C23 C24 -0.5(4) . . . . ?
N5 C20 C19 C18 -2.2(4) . . . . ?
C21 C20 C19 C18 179.0(2) . . . . ?
C22 C23 C24 C25 0.6(4) . . . . ?
N6 C25 C24 C23 0.5(4) . . . . ?
C5 N1 C1 C2 -1.4(4) . . . . ?
Pr1 N1 C1 C2 172.1(2) . . . . ?
N1 C1 C2 C3 -0.5(5) . . . . ?
C10 N2 C6 C7 -1.3(4) . . . . ?
Pr1 N2 C6 C7 169.65(18) . . . . ?
C10 N2 C6 C5 177.3(2) . . . . ?
Pr1 N2 C6 C5 -11.8(3) . . . . ?
N1 C5 C6 N2 0.8(3) . . . . ?
C4 C5 C6 N2 -177.2(3) . . . . ?
N1 C5 C6 C7 179.3(2) . . . . ?
C4 C5 C6 C7 1.3(4) . . . . ?
N2 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 C8 -177.2(2) . . . . ?
C6 C7 C8 C9 -0.1(4) . . . . ?
C10 C9 C8 C7 -1.0(4) . . . . ?
C20 C19 C18 C17 1.2(4) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
N1 C5 C4 C3 -0.7(5) . . . . ?
C6 C5 C4 C3 177.2(3) . . . . ?
C1 C2 C3 C4 1.8(5) . . . . ?
C5 C4 C3 C2 -1.3(5) . . . . ?

_refine_diff_density_max         2.015
_refine_diff_density_min         -1.275
_refine_diff_density_rms         0.088

_shelxl_version_number           2013-4


_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx_CCDC5
_database_code_depnum_ccdc_archive 'CCDC 1017810'
_audit_update_record             
;
2014-08-04 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_publcif_datablock.id            {8facc684-419f-441d-9f6e-ad8c1341ff76}
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H25 F6 N9 O6 P Pr'
_chemical_formula_weight         857.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2587(14)
_cell_length_b                   11.8157(12)
_cell_length_c                   20.586(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.7070(10)
_cell_angle_gamma                90
_cell_volume                     3202.9(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    90
_cell_measurement_reflns_used    9960
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.52

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_F_000             1704
_exptl_transmission_factor_min   1.19
_exptl_transmission_factor_max   1.51
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.663
_shelx_estimated_absorpt_T_min   0.662
_shelx_estimated_absorpt_T_max   0.838
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
SADABS Sheldrick 1996 
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      90
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            35152
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.739
_diffrn_reflns_theta_max         27.541
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7304
_reflns_number_gt                6673
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 

 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    Sir2011
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+44.2819P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7304
_refine_ls_number_parameters     452
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1416
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.35637(2) 0.21608(2) 0.36914(2) 0.01359(10) Uani 1 1 d . . . . .
P1 P 0.73544(16) -0.0627(2) 0.27835(12) 0.0437(5) Uani 1 1 d . . . . .
O1 O 0.3740(3) 0.0078(4) 0.3348(2) 0.0205(9) Uani 1 1 d . . . . .
O2 O 0.4785(3) 0.0629(3) 0.4178(2) 0.0204(9) Uani 1 1 d . . . . .
O3 O 0.4649(4) -0.1166(4) 0.3947(2) 0.0263(10) Uani 1 1 d . . . . .
O4 O 0.3616(3) 0.4337(4) 0.3554(2) 0.0221(9) Uani 1 1 d . . . . .
O5 O 0.2142(3) 0.3666(4) 0.3705(2) 0.0203(9) Uani 1 1 d . . . . .
O6 O 0.2302(4) 0.5471(4) 0.3520(2) 0.0285(10) Uani 1 1 d . . . . .
N1 N 0.2506(4) 0.0845(4) 0.4389(2) 0.0176(10) Uani 1 1 d . . . . .
N2 N 0.1726(3) 0.1533(4) 0.3191(2) 0.0154(9) Uani 1 1 d . . . . .
N3 N 0.2988(4) 0.2703(4) 0.2476(2) 0.0184(10) Uani 1 1 d . . . . .
N4 N 0.5056(4) 0.2164(4) 0.2994(3) 0.0201(10) Uani 1 1 d . . . . .
N5 N 0.5310(4) 0.2959(4) 0.4242(2) 0.0163(9) Uani 1 1 d . . . . .
N6 N 0.3647(4) 0.3042(4) 0.4876(2) 0.0181(10) Uani 1 1 d . . . . .
N7 N 0.4405(4) -0.0186(4) 0.3826(2) 0.0187(10) Uani 1 1 d . . . . .
N8 N 0.2669(4) 0.4515(4) 0.3587(2) 0.0199(10) Uani 1 1 d . . . . .
N9 N 0.0036(6) 0.3157(7) 0.4849(4) 0.056(2) Uani 1 1 d . . . . .
F1 F 0.7650(4) 0.0459(4) 0.3195(2) 0.0451(11) Uani 1 1 d . . . . .
F2 F 0.8471(3) -0.0742(4) 0.2570(2) 0.0337(9) Uani 1 1 d . . . . .
F3 F 0.6968(4) -0.1579(6) 0.2279(4) 0.080(2) Uani 1 1 d . . . . .
F4 F 0.6199(4) -0.0441(6) 0.2926(4) 0.0735(19) Uani 1 1 d . . . . .
F5 F 0.7127(4) 0.0276(5) 0.2156(2) 0.0574(14) Uani 1 1 d . . . . .
F6 F 0.7624(10) -0.1392(8) 0.3379(5) 0.150(5) Uani 1 1 d . . . . .
C1 C 0.2956(5) 0.0406(5) 0.4953(3) 0.0205(12) Uani 1 1 d . . . . .
H1 H 0.3618 0.0659 0.5114 0.025 Uiso 1 1 calc R U . . .
C2 C 0.2496(5) -0.0399(5) 0.5310(3) 0.0249(13) Uani 1 1 d . . . . .
H2 H 0.2844 -0.0700 0.5702 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1536(5) -0.0753(6) 0.5089(3) 0.0288(14) Uani 1 1 d . . . . .
H3 H 0.1206 -0.1301 0.5328 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1041(5) -0.0300(5) 0.4507(3) 0.0240(13) Uani 1 1 d . . . . .
H4 H 0.0374 -0.0534 0.4345 0.029 Uiso 1 1 calc R U . . .
C5 C 0.1554(4) 0.0502(5) 0.4174(3) 0.0173(11) Uani 1 1 d . . . . .
C6 C 0.1081(4) 0.1030(5) 0.3554(3) 0.0176(11) Uani 1 1 d . . . . .
C7 C 0.0036(5) 0.1011(5) 0.3365(3) 0.0216(12) Uani 1 1 d . . . . .
H7 H -0.0405 0.0639 0.3628 0.026 Uiso 1 1 calc R U . . .
C8 C -0.0353(4) 0.1542(5) 0.2787(3) 0.0225(12) Uani 1 1 d . . . . .
H8 H -0.1064 0.1546 0.2654 0.027 Uiso 1 1 calc R U . . .
C9 C 0.0306(5) 0.2064(5) 0.2407(3) 0.0216(12) Uani 1 1 d . . . . .
H9 H 0.0059 0.2434 0.2011 0.026 Uiso 1 1 calc R U . . .
C10 C 0.1340(4) 0.2032(5) 0.2621(3) 0.0162(11) Uani 1 1 d . . . . .
C11 C 0.2063(5) 0.2597(5) 0.2245(3) 0.0175(11) Uani 1 1 d . . . . .
H11 H 0.1838 0.2889 0.1823 0.021 Uiso 1 1 calc R U . . .
C12 C 0.3659(5) 0.3343(5) 0.2088(3) 0.0230(12) Uani 1 1 d . . . . .
H12A H 0.4003 0.3949 0.2362 0.028 Uiso 1 1 calc R U . . .
H12B H 0.3245 0.3705 0.1713 0.028 Uiso 1 1 calc R U . . .
C13 C 0.4459(5) 0.2584(6) 0.1831(3) 0.0253(13) Uani 1 1 d . . . . .
H13A H 0.5014 0.3066 0.1705 0.030 Uiso 1 1 calc R U . . .
H13B H 0.4147 0.2191 0.1433 0.030 Uiso 1 1 calc R U . . .
C14 C 0.4913(5) 0.1696(5) 0.2324(3) 0.0241(13) Uani 1 1 d . . . . .
H14A H 0.4455 0.1033 0.2311 0.029 Uiso 1 1 calc R U . . .
H14B H 0.5575 0.1439 0.2200 0.029 Uiso 1 1 calc R U . . .
C15 C 0.5951(5) 0.2401(5) 0.3246(3) 0.0210(12) Uani 1 1 d . . . . .
H15 H 0.6507 0.2285 0.3002 0.025 Uiso 1 1 calc R U . . .
C16 C 0.6131(5) 0.2855(5) 0.3916(3) 0.0205(12) Uani 1 1 d . . . . .
C17 C 0.7112(5) 0.3119(5) 0.4193(3) 0.0253(13) Uani 1 1 d . . . . .
H17 H 0.7671 0.3064 0.3945 0.030 Uiso 1 1 calc R U . . .
C18 C 0.7248(5) 0.3463(6) 0.4839(3) 0.0268(14) Uani 1 1 d . . . . .
H18 H 0.7910 0.3632 0.5046 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6411(5) 0.3561(5) 0.5185(3) 0.0244(13) Uani 1 1 d . . . . .
H19 H 0.6493 0.3789 0.5631 0.029 Uiso 1 1 calc R U . . .
C20 C 0.5446(5) 0.3317(5) 0.4863(3) 0.0187(11) Uani 1 1 d . . . . .
C21 C 0.4516(4) 0.3455(5) 0.5194(3) 0.0181(11) Uani 1 1 d . . . . .
C22 C 0.4537(5) 0.3986(5) 0.5802(3) 0.0221(12) Uani 1 1 d . . . . .
H22 H 0.5155 0.4285 0.6015 0.026 Uiso 1 1 calc R U . . .
C23 C 0.3653(5) 0.4071(5) 0.6090(3) 0.0242(13) Uani 1 1 d . . . . .
H23 H 0.3657 0.4419 0.6507 0.029 Uiso 1 1 calc R U . . .
C24 C 0.2755(5) 0.3646(6) 0.5767(3) 0.0251(13) Uani 1 1 d . . . . .
H24 H 0.2135 0.3698 0.5955 0.030 Uiso 1 1 calc R U . . .
C25 C 0.2791(5) 0.3143(5) 0.5163(3) 0.0223(12) Uani 1 1 d . . . . .
H25 H 0.2178 0.2854 0.4939 0.027 Uiso 1 1 calc R U . . .
C26 C -0.0119(6) 0.4553(9) 0.3882(4) 0.048(2) Uani 1 1 d . . . . .
H26A H -0.0383 0.4155 0.3480 0.073 Uiso 1 1 calc R U . . .
H26B H 0.0549 0.4873 0.3831 0.073 Uiso 1 1 calc R U . . .
H26C H -0.0586 0.5164 0.3966 0.073 Uiso 1 1 calc R U . . .
C27 C -0.0026(5) 0.3765(8) 0.4426(4) 0.0407(18) Uani 1 1 d . . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

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 O2 2.554(4) . ?
Pr1 N4 2.577(5) . ?
Pr1 O1 2.579(4) . ?
Pr1 N3 2.610(5) . ?
Pr1 O5 2.594(4) . ?
Pr1 N1 2.630(5) . ?
Pr1 N2 2.638(5) . ?
Pr1 N5 2.631(5) . ?
Pr1 N6 2.641(5) . ?
Pr1 O4 2.588(4) . ?
Pr1 N7 2.990(5) . ?
P1 F6 1.531(7) . ?
P1 F1 1.562(5) . ?
P1 F3 1.575(6) . ?
P1 F2 1.599(4) . ?
P1 F4 1.608(6) . ?
P1 F5 1.676(6) . ?
O1 N7 1.281(6) . ?
O2 N7 1.274(6) . ?
O3 N7 1.220(6) . ?
O4 N8 1.283(7) . ?
O5 N8 1.261(7) . ?
O6 N8 1.231(6) . ?
N1 C5 1.350(7) . ?
N1 C1 1.345(7) . ?
N2 C6 1.339(8) . ?
N2 C10 1.360(7) . ?
N3 C11 1.268(8) . ?
N3 C12 1.472(7) . ?
N4 C15 1.270(8) . ?
N4 C14 1.478(8) . ?
N5 C20 1.338(8) . ?
N5 C16 1.349(8) . ?
N6 C21 1.348(7) . ?
N6 C25 1.345(8) . ?
N9 C27 1.125(11) . ?
C1 C2 1.386(9) . ?
C1 H1 0.9500 . ?
C2 C3 1.367(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.490(8) . ?
C6 C7 1.394(8) . ?
C7 C8 1.390(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.462(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.529(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.531(9) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.473(9) . ?
C15 H15 0.9500 . ?
C16 C17 1.393(8) . ?
C17 C18 1.383(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.401(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.486(8) . ?
C21 C22 1.398(8) . ?
C22 C23 1.379(9) . ?
C22 H22 0.9500 . ?
C23 C24 1.389(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(9) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
C26 C27 1.451(12) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
O2 Pr1 N4 74.16(15) . . ?
O2 Pr1 O1 50.05(12) . . ?
N4 Pr1 O1 75.45(15) . . ?
O2 Pr1 N3 130.64(15) . . ?
N4 Pr1 N3 67.83(16) . . ?
O1 Pr1 N3 89.82(14) . . ?
O2 Pr1 O5 155.49(14) . . ?
N4 Pr1 O5 127.65(15) . . ?
O1 Pr1 O5 138.28(13) . . ?
N3 Pr1 O5 73.16(15) . . ?
O2 Pr1 N1 73.80(15) . . ?
N4 Pr1 N1 142.99(16) . . ?
O1 Pr1 N1 69.94(14) . . ?
N3 Pr1 N1 123.64(15) . . ?
O5 Pr1 N1 87.99(14) . . ?
O2 Pr1 N2 117.91(14) . . ?
N4 Pr1 N2 121.13(15) . . ?
O1 Pr1 N2 74.54(14) . . ?
N3 Pr1 N2 62.70(15) . . ?
O5 Pr1 N2 63.77(14) . . ?
N1 Pr1 N2 61.31(15) . . ?
O2 Pr1 N5 66.37(13) . . ?
N4 Pr1 N5 62.94(16) . . ?
O1 Pr1 N5 110.91(14) . . ?
N3 Pr1 N5 117.99(15) . . ?
O5 Pr1 N5 110.71(14) . . ?
N1 Pr1 N5 118.37(15) . . ?
N2 Pr1 N5 174.31(15) . . ?
O2 Pr1 N6 87.76(14) . . ?
N4 Pr1 N6 124.18(16) . . ?
O1 Pr1 N6 129.34(14) . . ?
N3 Pr1 N6 139.85(15) . . ?
O5 Pr1 N6 70.85(14) . . ?
N1 Pr1 N6 72.32(15) . . ?
N2 Pr1 N6 114.10(15) . . ?
N5 Pr1 N6 61.41(15) . . ?
O2 Pr1 O4 136.27(13) . . ?
N4 Pr1 O4 84.57(15) . . ?
O1 Pr1 O4 156.01(14) . . ?
N3 Pr1 O4 70.14(15) . . ?
O5 Pr1 O4 49.38(13) . . ?
N1 Pr1 O4 132.03(14) . . ?
N2 Pr1 O4 105.81(14) . . ?
N5 Pr1 O4 69.96(13) . . ?
N6 Pr1 O4 73.16(14) . . ?
O2 Pr1 N7 25.03(13) . . ?
N4 Pr1 N7 75.56(15) . . ?
O1 Pr1 N7 25.23(13) . . ?
N3 Pr1 N7 112.37(14) . . ?
O5 Pr1 N7 153.99(14) . . ?
N1 Pr1 N7 67.56(14) . . ?
N2 Pr1 N7 95.32(14) . . ?
N5 Pr1 N7 89.57(14) . . ?
N6 Pr1 N7 107.78(14) . . ?
O4 Pr1 N7 156.47(14) . . ?
F6 P1 F1 91.8(5) . . ?
F6 P1 F3 97.7(6) . . ?
F1 P1 F3 170.2(4) . . ?
F6 P1 F2 91.9(5) . . ?
F1 P1 F2 92.1(2) . . ?
F3 P1 F2 89.9(3) . . ?
F6 P1 F4 94.2(5) . . ?
F1 P1 F4 88.4(3) . . ?
F3 P1 F4 88.5(3) . . ?
F2 P1 F4 173.8(4) . . ?
F6 P1 F5 175.7(6) . . ?
F1 P1 F5 84.6(3) . . ?
F3 P1 F5 86.0(4) . . ?
F2 P1 F5 86.0(3) . . ?
F4 P1 F5 87.9(4) . . ?
N7 O1 Pr1 95.6(3) . . ?
N7 O2 Pr1 97.0(3) . . ?
N8 O4 Pr1 96.8(3) . . ?
N8 O5 Pr1 97.1(3) . . ?
C5 N1 C1 118.1(5) . . ?
C5 N1 Pr1 122.4(4) . . ?
C1 N1 Pr1 119.2(4) . . ?
C6 N2 C10 118.3(5) . . ?
C6 N2 Pr1 121.9(4) . . ?
C10 N2 Pr1 116.9(4) . . ?
C11 N3 C12 117.8(5) . . ?
C11 N3 Pr1 119.7(4) . . ?
C12 N3 Pr1 121.3(4) . . ?
C15 N4 C14 118.4(5) . . ?
C15 N4 Pr1 120.9(4) . . ?
C14 N4 Pr1 119.8(4) . . ?
C20 N5 C16 118.5(5) . . ?
C20 N5 Pr1 122.6(4) . . ?
C16 N5 Pr1 118.3(4) . . ?
C21 N6 C25 118.1(5) . . ?
C21 N6 Pr1 122.1(4) . . ?
C25 N6 Pr1 119.6(4) . . ?
O3 N7 O2 121.5(5) . . ?
O3 N7 O1 122.1(5) . . ?
O2 N7 O1 116.4(5) . . ?
O3 N7 Pr1 170.5(4) . . ?
O2 N7 Pr1 58.0(3) . . ?
O1 N7 Pr1 59.1(3) . . ?
O6 N8 O5 122.0(5) . . ?
O6 N8 O4 121.4(5) . . ?
O5 N8 O4 116.6(5) . . ?
N1 C1 C2 123.0(6) . . ?
N1 C1 H1 118.5 . . ?
C2 C1 H1 118.5 . . ?
C3 C2 C1 118.9(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.4(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 122.2(5) . . ?
N1 C5 C6 116.1(5) . . ?
C4 C5 C6 121.7(5) . . ?
N2 C6 C7 122.0(5) . . ?
N2 C6 C5 115.5(5) . . ?
C7 C6 C5 122.5(5) . . ?
C8 C7 C6 119.3(6) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 119.3(5) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 118.3(6) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
N2 C10 C9 122.9(6) . . ?
N2 C10 C11 116.8(5) . . ?
C9 C10 C11 120.3(5) . . ?
N3 C11 C10 120.8(5) . . ?
N3 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N3 C12 C13 111.9(5) . . ?
N3 C12 H12A 109.2 . . ?
C13 C12 H12A 109.2 . . ?
N3 C12 H12B 109.2 . . ?
C13 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 C14 114.1(5) . . ?
C12 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
C12 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
N4 C14 C13 111.1(5) . . ?
N4 C14 H14A 109.4 . . ?
C13 C14 H14A 109.4 . . ?
N4 C14 H14B 109.4 . . ?
C13 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N4 C15 C16 120.3(6) . . ?
N4 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
N5 C16 C17 123.0(6) . . ?
N5 C16 C15 116.5(5) . . ?
C17 C16 C15 120.4(6) . . ?
C16 C17 C18 118.1(6) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C19 C18 C17 119.6(6) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C18 C19 C20 118.7(6) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
N5 C20 C19 122.1(6) . . ?
N5 C20 C21 116.5(5) . . ?
C19 C20 C21 121.4(5) . . ?
N6 C21 C22 121.6(6) . . ?
N6 C21 C20 116.5(5) . . ?
C22 C21 C20 121.9(5) . . ?
C21 C22 C23 119.3(6) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 119.5(6) . . ?
C24 C23 H23 120.2 . . ?
C22 C23 H23 120.2 . . ?
C25 C24 C23 117.9(6) . . ?
C25 C24 H24 121.0 . . ?
C23 C24 H24 121.0 . . ?
N6 C25 C24 123.6(6) . . ?
N6 C25 H25 118.2 . . ?
C24 C25 H25 118.2 . . ?
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 179.3(10) . . ?

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 O2 N7 O3 -168.8(5) . . . . ?
Pr1 O2 N7 O1 9.7(5) . . . . ?
Pr1 O1 N7 O3 169.0(5) . . . . ?
Pr1 O1 N7 O2 -9.6(5) . . . . ?
Pr1 O5 N8 O6 177.3(5) . . . . ?
Pr1 O5 N8 O4 -4.1(5) . . . . ?
Pr1 O4 N8 O6 -177.2(5) . . . . ?
Pr1 O4 N8 O5 4.1(5) . . . . ?
C5 N1 C1 C2 1.7(9) . . . . ?
Pr1 N1 C1 C2 -172.0(5) . . . . ?
N1 C1 C2 C3 -1.2(10) . . . . ?
C1 C2 C3 C4 0.4(10) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C1 N1 C5 C4 -1.3(8) . . . . ?
Pr1 N1 C5 C4 172.1(4) . . . . ?
C1 N1 C5 C6 178.8(5) . . . . ?
Pr1 N1 C5 C6 -7.7(7) . . . . ?
C3 C4 C5 N1 0.6(9) . . . . ?
C3 C4 C5 C6 -179.6(6) . . . . ?
C10 N2 C6 C7 -0.3(8) . . . . ?
Pr1 N2 C6 C7 159.7(4) . . . . ?
C10 N2 C6 C5 -179.8(5) . . . . ?
Pr1 N2 C6 C5 -19.9(6) . . . . ?
N1 C5 C6 N2 17.6(7) . . . . ?
C4 C5 C6 N2 -162.2(5) . . . . ?
N1 C5 C6 C7 -161.9(5) . . . . ?
C4 C5 C6 C7 18.3(9) . . . . ?
N2 C6 C7 C8 -0.9(9) . . . . ?
C5 C6 C7 C8 178.6(5) . . . . ?
C6 C7 C8 C9 0.9(9) . . . . ?
C7 C8 C9 C10 0.2(9) . . . . ?
C6 N2 C10 C9 1.5(8) . . . . ?
Pr1 N2 C10 C9 -159.5(4) . . . . ?
C6 N2 C10 C11 178.5(5) . . . . ?
Pr1 N2 C10 C11 17.5(6) . . . . ?
C8 C9 C10 N2 -1.4(9) . . . . ?
C8 C9 C10 C11 -178.4(5) . . . . ?
C12 N3 C11 C10 -176.3(5) . . . . ?
Pr1 N3 C11 C10 -8.5(7) . . . . ?
N2 C10 C11 N3 -6.4(8) . . . . ?
C9 C10 C11 N3 170.7(6) . . . . ?
C11 N3 C12 C13 -112.8(6) . . . . ?
Pr1 N3 C12 C13 79.5(6) . . . . ?
N3 C12 C13 C14 -40.1(7) . . . . ?
C15 N4 C14 C13 -105.9(6) . . . . ?
Pr1 N4 C14 C13 84.6(5) . . . . ?
C12 C13 C14 N4 -38.2(7) . . . . ?
C14 N4 C15 C16 -179.2(5) . . . . ?
Pr1 N4 C15 C16 -9.8(7) . . . . ?
C20 N5 C16 C17 -1.0(9) . . . . ?
Pr1 N5 C16 C17 -171.9(5) . . . . ?
C20 N5 C16 C15 176.9(5) . . . . ?
Pr1 N5 C16 C15 6.0(6) . . . . ?
N4 C15 C16 N5 2.3(8) . . . . ?
N4 C15 C16 C17 -179.7(6) . . . . ?
N5 C16 C17 C18 2.5(9) . . . . ?
C15 C16 C17 C18 -175.3(6) . . . . ?
C16 C17 C18 C19 -1.5(9) . . . . ?
C17 C18 C19 C20 -0.7(9) . . . . ?
C16 N5 C20 C19 -1.4(8) . . . . ?
Pr1 N5 C20 C19 169.1(4) . . . . ?
C16 N5 C20 C21 178.0(5) . . . . ?
Pr1 N5 C20 C21 -11.5(7) . . . . ?
C18 C19 C20 N5 2.2(9) . . . . ?
C18 C19 C20 C21 -177.2(6) . . . . ?
C25 N6 C21 C22 -0.7(8) . . . . ?
Pr1 N6 C21 C22 175.7(4) . . . . ?
C25 N6 C21 C20 179.5(5) . . . . ?
Pr1 N6 C21 C20 -4.1(7) . . . . ?
N5 C20 C21 N6 10.0(8) . . . . ?
C19 C20 C21 N6 -170.6(5) . . . . ?
N5 C20 C21 C22 -169.9(5) . . . . ?
C19 C20 C21 C22 9.5(9) . . . . ?
N6 C21 C22 C23 1.3(9) . . . . ?
C20 C21 C22 C23 -178.9(5) . . . . ?
C21 C22 C23 C24 -1.0(9) . . . . ?
C22 C23 C24 C25 0.3(9) . . . . ?
C21 N6 C25 C24 -0.1(9) . . . . ?
Pr1 N6 C25 C24 -176.6(5) . . . . ?
C23 C24 C25 N6 0.3(10) . . . . ?

_refine_diff_density_max         3.669
_refine_diff_density_min         -2.204
_refine_diff_density_rms         0.170

_shelxl_version_number           2013-4


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
Datablock_name

