# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 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_R-1
_database_code_depnum_ccdc_archive 'CCDC 2015138'
loop_
_audit_author_name
_audit_author_address
'Xi-Li Li'
;zhengzhou University of Light Industry
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H36 Eu F9 N2 O6'
_chemical_formula_sum            'C47 H36 Eu F9 N2 O6'
_chemical_formula_weight         1047.74

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.6976(9)
_cell_length_b                   10.7310(6)
_cell_length_c                   11.1962(9)
_cell_angle_alpha                83.744(5)
_cell_angle_beta                 66.703(8)
_cell_angle_gamma                73.668(6)
_cell_volume                     1132.85(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4575
_cell_measurement_theta_min      3.8090
_cell_measurement_theta_max      25.2420

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    1.471
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.12994
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7845
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.434
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.715
_diffrn_reflns_point_group_measured_fraction_full 0.715
_reflns_number_total             5784
_reflns_number_gt                5544
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.437
_reflns_Friedel_fraction_max     0.435
_reflns_Friedel_fraction_full    0.435

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0436P)²] 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_abs_structure_details 
;
 Flack x determined using 1538 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.009(14)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5784
_refine_ls_number_parameters     588
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0408
_refine_ls_wR_factor_ref         0.0904
_refine_ls_wR_factor_gt          0.0892
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      0.999
_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
C1 C 0.9871(12) 0.9114(13) -0.1270(12) 0.071(3) Uani 1 1 d . . . . .
H1 H 1.0802 0.8772 -0.1351 0.085 Uiso 1 1 calc R U . . .
C2 C 0.9563(14) 0.9208(12) -0.2381(13) 0.073(3) Uani 1 1 d . . . . .
H2 H 1.0275 0.8946 -0.3188 0.087 Uiso 1 1 calc R U . . .
C3 C 0.8205(16) 0.9688(13) -0.2259(14) 0.081(4) Uani 1 1 d . . . . .
H3 H 0.7967 0.9733 -0.2980 0.097 Uiso 1 1 calc R U . . .
C4 C 0.7189(14) 1.0105(13) -0.1077(13) 0.072(3) Uani 1 1 d . . . . .
H4 H 0.6260 1.0464 -0.0996 0.087 Uiso 1 1 calc R U . . .
C5 C 0.7533(10) 0.9998(10) 0.0007(10) 0.048(2) Uani 1 1 d . . . . .
C6 C 0.6512(16) 1.0387(14) 0.1287(16) 0.042(4) Uani 1 1 d . . . . .
C7 C 0.5074(12) 1.0959(12) 0.1571(14) 0.070(3) Uani 1 1 d . . . . .
H7 H 0.4750 1.1111 0.0897 0.084 Uiso 1 1 calc R U . . .
C8 C 0.4138(11) 1.1298(11) 0.2809(12) 0.060(3) Uani 1 1 d . . . . .
C9 C 0.4643(10) 1.1060(10) 0.3816(11) 0.053(3) Uani 1 1 d . . . . .
C10 C 0.6082(16) 1.0464(15) 0.3478(17) 0.048(4) Uani 1 1 d . . . . .
H10 H 0.6428 1.0293 0.4137 0.058 Uiso 1 1 calc R U . . .
C11 C 0.2614(12) 1.2020(15) 0.3146(15) 0.088(4) Uani 1 1 d . . . . .
H11A H 0.2148 1.1520 0.2871 0.105 Uiso 1 1 calc R U . . .
H11B H 0.2552 1.2846 0.2696 0.105 Uiso 1 1 calc R U . . .
C12 C 0.1882(12) 1.2250(16) 0.4624(16) 0.090(5) Uani 1 1 d . . . . .
H12 H 0.0871 1.2675 0.4928 0.107 Uiso 1 1 calc R U . . .
C13 C 0.2273(13) 1.1033(16) 0.5391(17) 0.106(6) Uani 1 1 d . . . . .
H13A H 0.2450 1.0223 0.4969 0.127 Uiso 1 1 calc R U . . .
H13B H 0.1633 1.1045 0.6294 0.127 Uiso 1 1 calc R U . . .
C14 C 0.3616(14) 1.1445(15) 0.5177(16) 0.070(4) Uani 1 1 d . . . . .
H14 H 0.3983 1.1243 0.5870 0.084 Uiso 1 1 calc R U . . .
C15 C 0.2737(13) 1.2912(14) 0.5094(14) 0.084(4) Uani 1 1 d . . . . .
C16 C 0.3478(17) 1.3868(12) 0.4193(18) 0.105(5) Uani 1 1 d . . . . .
H16A H 0.2890 1.4735 0.4415 0.158 Uiso 1 1 calc R U . . .
H16B H 0.3661 1.3684 0.3310 0.158 Uiso 1 1 calc R U . . .
H16C H 0.4353 1.3790 0.4282 0.158 Uiso 1 1 calc R U . . .
C17 C 0.1879(17) 1.344(2) 0.6454(18) 0.137(8) Uani 1 1 d . . . . .
H17A H 0.2440 1.3792 0.6745 0.205 Uiso 1 1 calc R U . . .
H17B H 0.1587 1.2748 0.7026 0.205 Uiso 1 1 calc R U . . .
H17C H 0.1063 1.4105 0.6459 0.205 Uiso 1 1 calc R U . . .
C18 C 0.8210(15) 1.3621(14) -0.0591(14) 0.085(4) Uani 1 1 d . . . . .
H18 H 0.8441 1.2752 -0.0813 0.102 Uiso 1 1 calc R U . . .
C19 C 0.793(2) 1.452(2) -0.1445(18) 0.125(6) Uani 1 1 d . . . . .
H19 H 0.7784 1.4291 -0.2147 0.150 Uiso 1 1 calc R U . . .
C20 C 0.785(2) 1.584(2) -0.127(2) 0.144(9) Uani 1 1 d . . . . .
H20 H 0.7775 1.6468 -0.1893 0.172 Uiso 1 1 calc R U . . .
C21 C 0.789(2) 1.6147(16) -0.009(2) 0.138(9) Uani 1 1 d . . . . .
H21 H 0.7807 1.7005 0.0070 0.165 Uiso 1 1 calc R U . . .
C22 C 0.8059(15) 1.5209(12) 0.0832(16) 0.094(5) Uani 1 1 d . . . . .
H22 H 0.8093 1.5433 0.1596 0.113 Uiso 1 1 calc R U . . .
C23 C 0.8177(13) 1.3905(11) 0.0587(12) 0.073(4) Uani 1 1 d . . . . .
C24 C 0.8397(13) 1.2847(12) 0.1518(16) 0.050(3) Uani 1 1 d . . . . .
C25 C 0.7878(14) 1.3126(13) 0.2849(13) 0.058(3) Uani 1 1 d . . . . .
H25 H 0.7381 1.3974 0.3125 0.070 Uiso 1 1 calc R U . . .
C26 C 0.8067(10) 1.2206(9) 0.3773(9) 0.045(2) Uani 1 1 d . . . . .
C27 C 0.7418(12) 1.2594(12) 0.5179(12) 0.066(3) Uani 1 1 d . . . . .
C28 C 1.2582(12) 0.7590(11) 0.4333(11) 0.062(3) Uani 1 1 d . . . . .
H28 H 1.1620 0.7734 0.4542 0.075 Uiso 1 1 calc R U . . .
C29 C 1.3127(13) 0.7084(12) 0.5266(13) 0.073(3) Uani 1 1 d . . . . .
H29 H 1.2552 0.6859 0.6083 0.088 Uiso 1 1 calc R U . . .
C30 C 1.4552(14) 0.6922(12) 0.4954(14) 0.075(4) Uani 1 1 d . . . . .
H30 H 1.4938 0.6600 0.5573 0.090 Uiso 1 1 calc R U . . .
C31 C 1.5382(13) 0.7227(13) 0.3759(14) 0.078(4) Uani 1 1 d . . . . .
H31 H 1.6338 0.7107 0.3561 0.093 Uiso 1 1 calc R U . . .
C32 C 1.4836(11) 0.7716(11) 0.2823(12) 0.060(3) Uani 1 1 d . . . . .
H32 H 1.5418 0.7930 0.2004 0.073 Uiso 1 1 calc R U . . .
C33 C 1.3414(10) 0.7884(9) 0.3113(10) 0.047(2) Uani 1 1 d . . . . .
C34 C 1.2751(16) 0.8463(14) 0.2136(15) 0.040(4) Uani 1 1 d . . . . .
C35 C 1.3564(10) 0.8472(11) 0.0827(12) 0.051(3) Uani 1 1 d . . . . .
H35 H 1.4516 0.8042 0.0555 0.061 Uiso 1 1 calc R U . . .
C36 C 1.3065(17) 0.9072(16) -0.0104(16) 0.050(4) Uani 1 1 d . . . . .
C37 C 1.4033(11) 0.9013(13) -0.1512(12) 0.064(3) Uani 1 1 d . . . . .
C38 C 1.2899(14) 0.5452(13) -0.0554(14) 0.090(5) Uani 1 1 d . . . . .
H38 H 1.3006 0.6292 -0.0725 0.108 Uiso 1 1 calc R U . . .
C39 C 1.3850(17) 0.4456(15) -0.1376(15) 0.112(6) Uani 1 1 d . . . . .
H39 H 1.4653 0.4599 -0.2048 0.135 Uiso 1 1 calc R U . . .
C40 C 1.3606(18) 0.3253(16) -0.1198(17) 0.106(5) Uani 1 1 d . . . . .
H40 H 1.4230 0.2586 -0.1774 0.128 Uiso 1 1 calc R U . . .
C41 C 1.2454(16) 0.3014(12) -0.0180(14) 0.080(4) Uani 1 1 d . . . . .
H41 H 1.2274 0.2201 -0.0076 0.096 Uiso 1 1 calc R U . . .
C42 C 1.1576(13) 0.4003(11) 0.0680(12) 0.066(3) Uani 1 1 d . . . . .
H42 H 1.0814 0.3839 0.1390 0.080 Uiso 1 1 calc R U . . .
C43 C 1.1780(12) 0.5215(12) 0.0531(11) 0.058(3) Uani 1 1 d . . . . .
C44 C 1.0820(14) 0.6313(13) 0.1461(14) 0.048(3) Uani 1 1 d . . . . .
C45 C 1.0160(13) 0.6048(11) 0.2759(12) 0.058(3) Uani 1 1 d . . . . .
H45 H 1.0360 0.5191 0.3033 0.070 Uiso 1 1 calc R U . . .
C46 C 0.9216(9) 0.6983(10) 0.3677(10) 0.046(2) Uani 1 1 d . . . . .
C47 C 0.8659(12) 0.6621(11) 0.5067(10) 0.056(3) Uani 1 1 d . . . . .
Eu1 Eu 0.96360(3) 0.96011(3) 0.17960(3) 0.03992(14) Uani 1 1 d . . . . .
F1 F 0.6530(8) 1.1899(8) 0.5885(7) 0.093(2) Uani 1 1 d . . . . .
F2 F 0.8333(8) 1.2387(10) 0.5733(7) 0.109(3) Uani 1 1 d . . . . .
F3 F 0.6680(10) 1.3814(8) 0.5422(8) 0.116(3) Uani 1 1 d . . . . .
F4 F 1.4259(11) 1.0124(9) -0.1916(8) 0.122(3) Uani 1 1 d . . . . .
F5 F 1.5260(10) 0.8214(14) -0.1742(10) 0.142(5) Uani 1 1 d . . . . .
F6 F 1.3528(9) 0.8672(12) -0.2279(8) 0.128(4) Uani 1 1 d . . . . .
F7 F 0.7330(9) 0.6991(14) 0.5609(8) 0.159(5) Uani 1 1 d . . . . .
F8 F 0.9134(13) 0.7062(13) 0.5747(8) 0.152(5) Uani 1 1 d . . . . .
F9 F 0.8976(15) 0.5384(9) 0.5323(9) 0.171(6) Uani 1 1 d . . . . .
N1 N 0.8880(8) 0.9496(7) -0.0085(8) 0.047(2) Uani 1 1 d . . . . .
N2 N 0.6966(8) 1.0135(7) 0.2292(8) 0.0421(19) Uani 1 1 d . . . . .
O1 O 0.9096(7) 1.1754(6) 0.1050(7) 0.0518(17) Uani 1 1 d . . . . .
O2 O 0.8771(7) 1.1040(6) 0.3566(7) 0.0503(17) Uani 1 1 d . . . . .
O3 O 1.1783(7) 0.9693(7) 0.0083(6) 0.0518(17) Uani 1 1 d . . . . .
O4 O 1.1443(6) 0.8947(7) 0.2614(7) 0.0553(19) Uani 1 1 d . . . . .
O5 O 1.0671(7) 0.7442(6) 0.0987(7) 0.0533(18) Uani 1 1 d . . . . .
O6 O 0.8792(6) 0.8177(6) 0.3476(6) 0.0511(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
C1 N1 1.347(13) . ?
C1 C2 1.394(17) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.360(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.387(15) . ?
C4 H4 0.9300 . ?
C5 N1 1.354(12) . ?
C5 C6 1.434(18) . ?
C6 N2 1.366(18) . ?
C6 C7 1.403(19) . ?
C7 C8 1.365(17) . ?
C7 H7 0.9300 . ?
C8 C9 1.403(16) . ?
C8 C11 1.506(15) . ?
C9 C10 1.400(18) . ?
C9 C14 1.503(19) . ?
C10 N2 1.305(17) . ?
C10 H10 0.9300 . ?
C11 C12 1.54(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.53(2) . ?
C12 C15 1.56(2) . ?
C12 H12 0.9800 . ?
C13 C14 1.54(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.60(2) . ?
C14 H14 0.9800 . ?
C15 C17 1.51(2) . ?
C15 C16 1.52(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.34(2) . ?
C18 C23 1.371(19) . ?
C18 H18 0.9300 . ?
C19 C20 1.42(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.41(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.39(2) . ?
C21 H21 0.9300 . ?
C22 C23 1.416(18) . ?
C22 H22 0.9300 . ?
C23 C24 1.488(18) . ?
C24 O1 1.241(14) . ?
C24 C25 1.403(18) . ?
C25 C26 1.385(16) . ?
C25 H25 0.9300 . ?
C26 O2 1.257(11) . ?
C26 C27 1.499(15) . ?
C27 F2 1.312(14) . ?
C27 F3 1.318(13) . ?
C27 F1 1.326(14) . ?
C28 C33 1.364(15) . ?
C28 C29 1.381(15) . ?
C28 H28 0.9300 . ?
C29 C30 1.385(17) . ?
C29 H29 0.9300 . ?
C30 C31 1.347(18) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(16) . ?
C31 H31 0.9300 . ?
C32 C33 1.385(14) . ?
C32 H32 0.9300 . ?
C33 C34 1.518(18) . ?
C34 O4 1.254(16) . ?
C34 C35 1.377(19) . ?
C35 C36 1.374(18) . ?
C35 H35 0.9300 . ?
C36 O3 1.287(17) . ?
C36 C37 1.50(2) . ?
C37 F4 1.281(14) . ?
C37 F5 1.294(13) . ?
C37 F6 1.307(14) . ?
C38 C39 1.374(17) . ?
C38 C43 1.388(16) . ?
C38 H38 0.9300 . ?
C39 C40 1.37(2) . ?
C39 H39 0.9300 . ?
C40 C41 1.37(2) . ?
C40 H40 0.9300 . ?
C41 C42 1.372(16) . ?
C41 H41 0.9300 . ?
C42 C43 1.361(17) . ?
C42 H42 0.9300 . ?
C43 C44 1.506(16) . ?
C44 O5 1.262(15) . ?
C44 C45 1.380(18) . ?
C45 C46 1.385(14) . ?
C45 H45 0.9300 . ?
C46 O6 1.261(11) . ?
C46 C47 1.481(14) . ?
C47 F8 1.258(13) . ?
C47 F7 1.265(13) . ?
C47 F9 1.303(14) . ?
Eu1 O6 2.344(6) . ?
Eu1 O3 2.359(6) . ?
Eu1 O4 2.359(7) . ?
Eu1 O1 2.362(6) . ?
Eu1 O2 2.362(6) . ?
Eu1 O5 2.374(7) . ?
Eu1 N1 2.560(9) . ?
Eu1 N2 2.586(7) . ?

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
N1 C1 C2 122.9(11) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C3 C2 C1 118.5(12) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 119.7(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C5 120.2(11) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 121.2(10) . . ?
N1 C5 C6 115.6(10) . . ?
C4 C5 C6 123.2(11) . . ?
N2 C6 C7 118.4(13) . . ?
N2 C6 C5 117.6(12) . . ?
C7 C6 C5 124.0(14) . . ?
C8 C7 C6 121.9(12) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 118.4(9) . . ?
C7 C8 C11 123.7(11) . . ?
C9 C8 C11 117.6(11) . . ?
C8 C9 C10 117.2(12) . . ?
C8 C9 C14 118.5(10) . . ?
C10 C9 C14 124.3(13) . . ?
N2 C10 C9 123.9(15) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
C8 C11 C12 109.5(11) . . ?
C8 C11 H11A 109.8 . . ?
C12 C11 H11A 109.8 . . ?
C8 C11 H11B 109.8 . . ?
C12 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?
C13 C12 C11 112.0(13) . . ?
C13 C12 C15 88.9(12) . . ?
C11 C12 C15 109.8(11) . . ?
C13 C12 H12 114.5 . . ?
C11 C12 H12 114.5 . . ?
C15 C12 H12 114.5 . . ?
C12 C13 C14 86.8(11) . . ?
C12 C13 H13A 114.2 . . ?
C14 C13 H13A 114.2 . . ?
C12 C13 H13B 114.2 . . ?
C14 C13 H13B 114.2 . . ?
H13A C13 H13B 111.4 . . ?
C9 C14 C13 107.5(13) . . ?
C9 C14 C15 106.3(12) . . ?
C13 C14 C15 87.1(10) . . ?
C9 C14 H14 117.2 . . ?
C13 C14 H14 117.2 . . ?
C15 C14 H14 117.2 . . ?
C17 C15 C16 112.5(15) . . ?
C17 C15 C12 110.7(13) . . ?
C16 C15 C12 118.3(14) . . ?
C17 C15 C14 108.7(14) . . ?
C16 C15 C14 119.7(11) . . ?
C12 C15 C14 83.6(11) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C23 123.9(16) . . ?
C19 C18 H18 118.1 . . ?
C23 C18 H18 118.1 . . ?
C18 C19 C20 119(2) . . ?
C18 C19 H19 120.3 . . ?
C20 C19 H19 120.3 . . ?
C21 C20 C19 116.9(19) . . ?
C21 C20 H20 121.6 . . ?
C19 C20 H20 121.6 . . ?
C22 C21 C20 122.2(19) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C21 C22 C23 118.7(17) . . ?
C21 C22 H22 120.6 . . ?
C23 C22 H22 120.6 . . ?
C18 C23 C22 117.9(13) . . ?
C18 C23 C24 120.4(13) . . ?
C22 C23 C24 121.5(14) . . ?
O1 C24 C25 123.2(13) . . ?
O1 C24 C23 116.9(13) . . ?
C25 C24 C23 119.8(12) . . ?
C26 C25 C24 123.4(13) . . ?
C26 C25 H25 118.3 . . ?
C24 C25 H25 118.3 . . ?
O2 C26 C25 126.7(10) . . ?
O2 C26 C27 114.1(9) . . ?
C25 C26 C27 119.2(10) . . ?
F2 C27 F3 106.5(11) . . ?
F2 C27 F1 103.8(11) . . ?
F3 C27 F1 105.0(9) . . ?
F2 C27 C26 113.7(9) . . ?
F3 C27 C26 115.3(11) . . ?
F1 C27 C26 111.4(10) . . ?
C33 C28 C29 121.9(11) . . ?
C33 C28 H28 119.1 . . ?
C29 C28 H28 119.1 . . ?
C28 C29 C30 118.3(12) . . ?
C28 C29 H29 120.8 . . ?
C30 C29 H29 120.8 . . ?
C31 C30 C29 120.4(12) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 121.1(11) . . ?
C30 C31 H31 119.5 . . ?
C32 C31 H31 119.5 . . ?
C31 C32 C33 119.5(11) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C28 C33 C32 118.8(10) . . ?
C28 C33 C34 119.5(10) . . ?
C32 C33 C34 121.6(11) . . ?
O4 C34 C35 123.8(14) . . ?
O4 C34 C33 115.2(12) . . ?
C35 C34 C33 121.0(12) . . ?
C36 C35 C34 124.5(13) . . ?
C36 C35 H35 117.7 . . ?
C34 C35 H35 117.7 . . ?
O3 C36 C35 126.6(14) . . ?
O3 C36 C37 112.8(13) . . ?
C35 C36 C37 120.6(14) . . ?
F4 C37 F5 106.0(12) . . ?
F4 C37 F6 106.1(12) . . ?
F5 C37 F6 106.5(12) . . ?
F4 C37 C36 111.1(11) . . ?
F5 C37 C36 113.4(12) . . ?
F6 C37 C36 113.2(11) . . ?
C39 C38 C43 120.5(13) . . ?
C39 C38 H38 119.7 . . ?
C43 C38 H38 119.7 . . ?
C40 C39 C38 119.4(13) . . ?
C40 C39 H39 120.3 . . ?
C38 C39 H39 120.3 . . ?
C39 C40 C41 121.0(12) . . ?
C39 C40 H40 119.5 . . ?
C41 C40 H40 119.5 . . ?
C42 C41 C40 118.3(13) . . ?
C42 C41 H41 120.8 . . ?
C40 C41 H41 120.8 . . ?
C43 C42 C41 122.3(12) . . ?
C43 C42 H42 118.8 . . ?
C41 C42 H42 118.8 . . ?
C42 C43 C38 118.0(11) . . ?
C42 C43 C44 123.0(11) . . ?
C38 C43 C44 119.0(11) . . ?
O5 C44 C45 123.7(12) . . ?
O5 C44 C43 116.8(12) . . ?
C45 C44 C43 119.6(11) . . ?
C44 C45 C46 123.8(11) . . ?
C44 C45 H45 118.1 . . ?
C46 C45 H45 118.1 . . ?
O6 C46 C45 126.8(10) . . ?
O6 C46 C47 113.4(9) . . ?
C45 C46 C47 119.7(10) . . ?
F8 C47 F7 106.4(12) . . ?
F8 C47 F9 101.2(12) . . ?
F7 C47 F9 104.8(11) . . ?
F8 C47 C46 113.5(10) . . ?
F7 C47 C46 113.6(9) . . ?
F9 C47 C46 116.1(10) . . ?
O6 Eu1 O3 138.0(2) . . ?
O6 Eu1 O4 77.3(2) . . ?
O3 Eu1 O4 71.8(2) . . ?
O6 Eu1 O1 143.3(2) . . ?
O3 Eu1 O1 77.9(2) . . ?
O4 Eu1 O1 118.8(3) . . ?
O6 Eu1 O2 81.7(2) . . ?
O3 Eu1 O2 117.8(2) . . ?
O4 Eu1 O2 78.1(2) . . ?
O1 Eu1 O2 71.1(2) . . ?
O6 Eu1 O5 71.4(2) . . ?
O3 Eu1 O5 75.6(2) . . ?
O4 Eu1 O5 79.7(3) . . ?
O1 Eu1 O5 140.3(2) . . ?
O2 Eu1 O5 148.2(2) . . ?
O6 Eu1 N1 111.6(2) . . ?
O3 Eu1 N1 82.6(2) . . ?
O4 Eu1 N1 147.1(2) . . ?
O1 Eu1 N1 73.8(2) . . ?
O2 Eu1 N1 133.5(2) . . ?
O5 Eu1 N1 74.0(3) . . ?
O6 Eu1 N2 75.4(2) . . ?
O3 Eu1 N2 140.7(2) . . ?
O4 Eu1 N2 147.3(2) . . ?
O1 Eu1 N2 76.1(2) . . ?
O2 Eu1 N2 80.5(2) . . ?
O5 Eu1 N2 107.8(2) . . ?
N1 Eu1 N2 62.1(2) . . ?
C1 N1 C5 117.5(9) . . ?
C1 N1 Eu1 119.4(7) . . ?
C5 N1 Eu1 122.3(6) . . ?
C10 N2 C6 120.2(12) . . ?
C10 N2 Eu1 118.3(9) . . ?
C6 N2 Eu1 119.3(8) . . ?
C24 O1 Eu1 138.0(8) . . ?
C26 O2 Eu1 134.2(6) . . ?
C36 O3 Eu1 131.2(8) . . ?
C34 O4 Eu1 135.4(8) . . ?
C44 O5 Eu1 136.8(8) . . ?
C46 O6 Eu1 134.2(6) . . ?

_refine_diff_density_max         0.769
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_S-1
_database_code_depnum_ccdc_archive 'CCDC 2015139'
loop_
_audit_author_name
_audit_author_address
'Xi-Li Li'
;zhengzhou University of Light Industry
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H36 Eu F9 N2 O6'
_chemical_formula_sum            'C47 H36 Eu F9 N2 O6'
_chemical_formula_weight         1047.74

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

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.7349(3)
_cell_length_b                   10.7689(2)
_cell_length_c                   11.1509(4)
_cell_angle_alpha                83.873(2)
_cell_angle_beta                 66.744(3)
_cell_angle_gamma                74.512(2)
_cell_volume                     1141.33(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5571
_cell_measurement_theta_min      3.2269
_cell_measurement_theta_max      29.2248

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             524
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_exptl_absorpt_coefficient_mu    1.460
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97206
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8437
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.233
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_point_group_measured_fraction_full 0.701
_reflns_number_total             5728
_reflns_number_gt                5346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.405
_reflns_Friedel_fraction_max     0.404
_reflns_Friedel_fraction_full    0.404

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0397P)²] 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_abs_structure_details 
;
 Flack x determined using 1328 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0100(11)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5728
_refine_ls_number_parameters     588
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0384
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   0.965
_refine_ls_restrained_S_all      0.964
_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
C1 C 0.1943(9) 0.6952(8) 1.2970(9) 0.060(2) Uani 1 1 d . . . . .
H1 H 0.1027 0.7295 1.3035 0.072 Uiso 1 1 calc R U . . .
C2 C 0.2234(11) 0.6876(9) 1.4083(9) 0.070(3) Uani 1 1 d . . . . .
H2 H 0.1526 0.7160 1.4882 0.084 Uiso 1 1 calc R U . . .
C3 C 0.3570(13) 0.6381(9) 1.3988(10) 0.077(3) Uani 1 1 d . . . . .
H3 H 0.3792 0.6327 1.4721 0.093 Uiso 1 1 calc R U . . .
C4 C 0.4574(10) 0.5968(8) 1.2819(9) 0.062(2) Uani 1 1 d . . . . .
H4 H 0.5490 0.5614 1.2749 0.075 Uiso 1 1 calc R U . . .
C5 C 0.4247(8) 0.6068(6) 1.1712(8) 0.0432(18) Uani 1 1 d . . . . .
C6 C 0.5287(13) 0.5658(11) 1.0399(12) 0.045(3) Uani 1 1 d . . . . .
C7 C 0.6697(10) 0.5095(8) 1.0167(11) 0.061(2) Uani 1 1 d . . . . .
H7 H 0.6986 0.4938 1.0865 0.074 Uiso 1 1 calc R U . . .
C8 C 0.7664(8) 0.4770(8) 0.8924(10) 0.057(2) Uani 1 1 d . . . . .
C9 C 0.7188(8) 0.5016(7) 0.7910(9) 0.049(2) Uani 1 1 d . . . . .
C10 C 0.5800(14) 0.5622(12) 0.8185(14) 0.049(3) Uani 1 1 d . . . . .
H10 H 0.5495 0.5829 0.7498 0.058 Uiso 1 1 calc R U . . .
C11 C 0.9191(10) 0.4083(11) 0.8589(13) 0.087(3) Uani 1 1 d . . . . .
H11A H 0.9257 0.3271 0.9058 0.104 Uiso 1 1 calc R U . . .
H11B H 0.9643 0.4607 0.8859 0.104 Uiso 1 1 calc R U . . .
C12 C 0.9928(10) 0.3835(11) 0.7138(13) 0.088(3) Uani 1 1 d . . . . .
H12 H 1.0930 0.3420 0.6852 0.106 Uiso 1 1 calc R U . . .
C13 C 0.9565(10) 0.5061(12) 0.6369(12) 0.099(4) Uani 1 1 d . . . . .
H13A H 1.0213 0.5061 0.5468 0.119 Uiso 1 1 calc R U . . .
H13B H 0.9393 0.5859 0.6804 0.119 Uiso 1 1 calc R U . . .
C14 C 0.8220(12) 0.4649(12) 0.6556(14) 0.075(4) Uani 1 1 d . . . . .
H14 H 0.7872 0.4860 0.5850 0.090 Uiso 1 1 calc R U . . .
C15 C 0.9099(10) 0.3183(9) 0.6620(11) 0.074(3) Uani 1 1 d . . . . .
C16 C 0.8352(13) 0.2235(9) 0.7490(15) 0.115(5) Uani 1 1 d . . . . .
H16A H 0.9013 0.1426 0.7462 0.173 Uiso 1 1 calc R U . . .
H16B H 0.7663 0.2116 0.7196 0.173 Uiso 1 1 calc R U . . .
H16C H 0.7902 0.2555 0.8368 0.173 Uiso 1 1 calc R U . . .
C17 C 0.9958(13) 0.2631(13) 0.5293(14) 0.131(5) Uani 1 1 d . . . . .
H17A H 0.9390 0.2308 0.4982 0.196 Uiso 1 1 calc R U . . .
H17B H 1.0723 0.1941 0.5330 0.196 Uiso 1 1 calc R U . . .
H17C H 1.0318 0.3289 0.4712 0.196 Uiso 1 1 calc R U . . .
C18 C 0.3636(12) 0.2424(10) 1.2220(10) 0.085(3) Uani 1 1 d . . . . .
H18 H 0.3423 0.3284 1.2446 0.102 Uiso 1 1 calc R U . . .
C19 C 0.3883(15) 0.1493(15) 1.3097(12) 0.121(5) Uani 1 1 d . . . . .
H19 H 0.3949 0.1709 1.3851 0.145 Uiso 1 1 calc R U . . .
C20 C 0.4029(18) 0.0228(16) 1.2832(15) 0.149(7) Uani 1 1 d . . . . .
H20 H 0.4177 -0.0407 1.3429 0.179 Uiso 1 1 calc R U . . .
C21 C 0.3964(16) -0.0123(12) 1.1716(16) 0.124(5) Uani 1 1 d . . . . .
H21 H 0.4015 -0.0974 1.1577 0.149 Uiso 1 1 calc R U . . .
C22 C 0.3818(12) 0.0837(10) 1.0786(11) 0.094(4) Uani 1 1 d . . . . .
H22 H 0.3805 0.0617 1.0007 0.113 Uiso 1 1 calc R U . . .
C23 C 0.3690(10) 0.2146(8) 1.1033(9) 0.063(2) Uani 1 1 d . . . . .
C24 C 0.3433(9) 0.3185(8) 1.0115(10) 0.041(2) Uani 1 1 d . . . . .
C25 C 0.3990(11) 0.2917(10) 0.8758(10) 0.056(3) Uani 1 1 d . . . . .
H25 H 0.4513 0.2090 0.8466 0.067 Uiso 1 1 calc R U . . .
C26 C 0.3775(8) 0.3850(7) 0.7862(7) 0.0408(18) Uani 1 1 d . . . . .
C27 C 0.4466(10) 0.3462(8) 0.6422(9) 0.058(2) Uani 1 1 d . . . . .
C28 C -0.0774(9) 0.8536(8) 0.7321(8) 0.057(2) Uani 1 1 d . . . . .
H28 H 0.0175 0.8435 0.7120 0.068 Uiso 1 1 calc R U . . .
C29 C -0.1330(11) 0.9038(9) 0.6387(9) 0.068(3) Uani 1 1 d . . . . .
H29 H -0.0765 0.9284 0.5571 0.082 Uiso 1 1 calc R U . . .
C30 C -0.2716(12) 0.9164(9) 0.6689(12) 0.075(3) Uani 1 1 d . . . . .
H30 H -0.3094 0.9490 0.6066 0.090 Uiso 1 1 calc R U . . .
C31 C -0.3552(11) 0.8825(9) 0.7873(12) 0.074(3) Uani 1 1 d . . . . .
H31 H -0.4496 0.8915 0.8061 0.089 Uiso 1 1 calc R U . . .
C32 C -0.3000(9) 0.8341(8) 0.8809(9) 0.061(2) Uani 1 1 d . . . . .
H32 H -0.3578 0.8118 0.9630 0.073 Uiso 1 1 calc R U . . .
C33 C -0.1593(8) 0.8189(7) 0.8525(8) 0.0420(18) Uani 1 1 d . . . . .
C34 C -0.0949(13) 0.7578(11) 0.9488(12) 0.047(3) Uani 1 1 d . . . . .
C35 C -0.1760(10) 0.7591(8) 1.0848(10) 0.054(2) Uani 1 1 d . . . . .
H35 H -0.2700 0.8026 1.1145 0.064 Uiso 1 1 calc R U . . .
C36 C -0.1229(14) 0.7008(12) 1.1716(13) 0.046(3) Uani 1 1 d . . . . .
C37 C -0.2210(9) 0.7033(8) 1.3176(9) 0.055(2) Uani 1 1 d . . . . .
C38 C -0.1023(12) 1.0598(9) 1.2214(10) 0.088(4) Uani 1 1 d . . . . .
H38 H -0.1133 0.9761 1.2389 0.106 Uiso 1 1 calc R U . . .
C39 C -0.1976(13) 1.1602(11) 1.3052(12) 0.108(4) Uani 1 1 d . . . . .
H39 H -0.2777 1.1453 1.3722 0.129 Uiso 1 1 calc R U . . .
C40 C -0.1737(14) 1.2758(11) 1.2892(12) 0.092(3) Uani 1 1 d . . . . .
H40 H -0.2352 1.3409 1.3478 0.111 Uiso 1 1 calc R U . . .
C41 C -0.0606(13) 1.3016(9) 1.1884(11) 0.081(3) Uani 1 1 d . . . . .
H41 H -0.0431 1.3829 1.1788 0.098 Uiso 1 1 calc R U . . .
C42 C 0.0278(10) 1.2047(8) 1.1005(9) 0.063(2) Uani 1 1 d . . . . .
H42 H 0.1039 1.2220 1.0299 0.076 Uiso 1 1 calc R U . . .
C43 C 0.0056(10) 1.0840(8) 1.1153(8) 0.051(2) Uani 1 1 d . . . . .
C44 C 0.0992(11) 0.9743(9) 1.0245(11) 0.044(3) Uani 1 1 d . . . . .
C45 C 0.1675(10) 1.0026(8) 0.8903(9) 0.049(2) Uani 1 1 d . . . . .
H45 H 0.1485 1.0878 0.8631 0.059 Uiso 1 1 calc R U . . .
C46 C 0.2603(8) 0.9107(7) 0.7983(7) 0.0407(18) Uani 1 1 d . . . . .
C47 C 0.3158(10) 0.9517(8) 0.6582(8) 0.053(2) Uani 1 1 d . . . . .
Eu1 Eu 0.21924(3) 0.64507(3) 0.98458(3) 0.04316(12) Uani 1 1 d . . . . .
F1 F 0.5213(8) 0.2253(5) 0.6182(6) 0.109(2) Uani 1 1 d . . . . .
F2 F 0.5328(6) 0.4199(6) 0.5727(5) 0.0883(17) Uani 1 1 d . . . . .
F3 F 0.3555(6) 0.3618(6) 0.5874(5) 0.0931(18) Uani 1 1 d . . . . .
F4 F -0.2461(7) 0.5921(6) 1.3591(6) 0.107(2) Uani 1 1 d . . . . .
F5 F -0.1699(7) 0.7396(8) 1.3935(6) 0.113(2) Uani 1 1 d . . . . .
F6 F -0.3448(9) 0.7825(10) 1.3414(8) 0.132(4) Uani 1 1 d . . . . .
F7 F 0.4485(7) 0.9144(9) 0.6010(6) 0.140(3) Uani 1 1 d . . . . .
F8 F 0.2694(9) 0.9065(9) 0.5886(6) 0.135(3) Uani 1 1 d . . . . .
F9 F 0.2846(10) 1.0734(7) 0.6354(6) 0.156(4) Uani 1 1 d . . . . .
N1 N 0.2931(7) 0.6549(6) 1.1808(6) 0.0459(15) Uani 1 1 d . . . . .
N2 N 0.4867(7) 0.5926(5) 0.9410(6) 0.0426(15) Uani 1 1 d . . . . .
O1 O 0.2729(5) 0.4257(4) 1.0589(5) 0.0465(13) Uani 1 1 d . . . . .
O2 O 0.3089(5) 0.4996(5) 0.8041(5) 0.0467(13) Uani 1 1 d . . . . .
O3 O 0.0009(5) 0.6347(4) 1.1571(5) 0.0434(12) Uani 1 1 d . . . . .
O4 O 0.0347(6) 0.7122(5) 0.9030(5) 0.0523(14) Uani 1 1 d . . . . .
O5 O 0.1168(6) 0.8622(5) 1.0687(5) 0.0510(14) Uani 1 1 d . . . . .
O6 O 0.3055(5) 0.7927(5) 0.8162(5) 0.0471(13) 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
C1 N1 1.334(10) . ?
C1 C2 1.384(12) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(13) . ?
C2 H2 0.9300 . ?
C3 C4 1.348(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.397(11) . ?
C4 H4 0.9300 . ?
C5 N1 1.333(9) . ?
C5 C6 1.472(14) . ?
C6 N2 1.326(14) . ?
C6 C7 1.400(15) . ?
C7 C8 1.377(13) . ?
C7 H7 0.9300 . ?
C8 C9 1.390(12) . ?
C8 C11 1.517(12) . ?
C9 C10 1.380(15) . ?
C9 C14 1.495(16) . ?
C10 N2 1.348(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.511(16) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.543(16) . ?
C12 C15 1.564(15) . ?
C12 H12 0.9800 . ?
C13 C14 1.553(16) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.619(15) . ?
C14 H14 0.9800 . ?
C15 C16 1.495(16) . ?
C15 C17 1.487(16) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C23 1.364(13) . ?
C18 C19 1.373(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.38(2) . ?
C19 H19 0.9300 . ?
C20 C21 1.37(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.408(16) . ?
C21 H21 0.9300 . ?
C22 C23 1.425(14) . ?
C22 H22 0.9300 . ?
C23 C24 1.480(13) . ?
C24 O1 1.238(9) . ?
C24 C25 1.419(13) . ?
C25 C26 1.381(12) . ?
C25 H25 0.9300 . ?
C26 O2 1.247(8) . ?
C26 C27 1.529(11) . ?
C27 F3 1.312(10) . ?
C27 F1 1.326(10) . ?
C27 F2 1.334(10) . ?
C28 C33 1.361(12) . ?
C28 C29 1.390(12) . ?
C28 H28 0.9300 . ?
C29 C30 1.361(13) . ?
C29 H29 0.9300 . ?
C30 C31 1.349(14) . ?
C30 H30 0.9300 . ?
C31 C32 1.385(12) . ?
C31 H31 0.9300 . ?
C32 C33 1.381(11) . ?
C32 H32 0.9300 . ?
C33 C34 1.503(15) . ?
C34 O4 1.251(13) . ?
C34 C35 1.418(16) . ?
C35 C36 1.331(15) . ?
C35 H35 0.9300 . ?
C36 O3 1.284(14) . ?
C36 C37 1.549(16) . ?
C37 F4 1.295(10) . ?
C37 F5 1.312(10) . ?
C37 F6 1.314(11) . ?
C38 C43 1.350(13) . ?
C38 C39 1.400(13) . ?
C38 H38 0.9300 . ?
C39 C40 1.317(15) . ?
C39 H39 0.9300 . ?
C40 C41 1.361(16) . ?
C40 H40 0.9300 . ?
C41 C42 1.380(13) . ?
C41 H41 0.9300 . ?
C42 C43 1.365(12) . ?
C42 H42 0.9300 . ?
C43 C44 1.499(12) . ?
C44 O5 1.249(11) . ?
C44 C45 1.422(13) . ?
C45 C46 1.382(11) . ?
C45 H45 0.9300 . ?
C46 O6 1.258(8) . ?
C46 C47 1.499(11) . ?
C47 F8 1.266(10) . ?
C47 F7 1.276(10) . ?
C47 F9 1.287(10) . ?
Eu1 O6 2.385(5) . ?
Eu1 O3 2.396(5) . ?
Eu1 O2 2.402(5) . ?
Eu1 O4 2.407(5) . ?
Eu1 O5 2.416(5) . ?
Eu1 O1 2.415(5) . ?
Eu1 N2 2.625(6) . ?
Eu1 N1 2.626(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
N1 C1 C2 122.3(8) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.8(9) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C4 C3 C2 119.3(9) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.5(8) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 120.2(7) . . ?
N1 C5 C6 116.1(8) . . ?
C4 C5 C6 123.7(8) . . ?
N2 C6 C7 120.1(10) . . ?
N2 C6 C5 117.6(10) . . ?
C7 C6 C5 122.1(10) . . ?
C8 C7 C6 121.2(9) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C9 C8 C7 117.6(7) . . ?
C9 C8 C11 117.5(9) . . ?
C7 C8 C11 124.8(9) . . ?
C10 C9 C8 118.9(10) . . ?
C10 C9 C14 122.8(10) . . ?
C8 C9 C14 118.3(8) . . ?
N2 C10 C9 122.5(12) . . ?
N2 C10 H10 118.7 . . ?
C9 C10 H10 118.7 . . ?
C8 C11 C12 110.4(9) . . ?
C8 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
C8 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C11 C12 C13 110.4(9) . . ?
C11 C12 C15 111.3(9) . . ?
C13 C12 C15 88.9(9) . . ?
C11 C12 H12 114.5 . . ?
C13 C12 H12 114.5 . . ?
C15 C12 H12 114.5 . . ?
C12 C13 C14 86.7(8) . . ?
C12 C13 H13A 114.2 . . ?
C14 C13 H13A 114.2 . . ?
C12 C13 H13B 114.2 . . ?
C14 C13 H13B 114.2 . . ?
H13A C13 H13B 111.4 . . ?
C9 C14 C13 107.6(10) . . ?
C9 C14 C15 107.2(10) . . ?
C13 C14 C15 86.5(8) . . ?
C9 C14 H14 117.1 . . ?
C13 C14 H14 117.1 . . ?
C15 C14 H14 117.1 . . ?
C16 C15 C17 110.3(10) . . ?
C16 C15 C12 117.9(10) . . ?
C17 C15 C12 112.1(10) . . ?
C16 C15 C14 119.0(9) . . ?
C17 C15 C14 111.5(10) . . ?
C12 C15 C14 83.7(8) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 123.0(11) . . ?
C23 C18 H18 118.5 . . ?
C19 C18 H18 118.5 . . ?
C20 C19 C18 118.3(14) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 122.1(13) . . ?
C19 C20 H20 118.9 . . ?
C21 C20 H20 118.9 . . ?
C20 C21 C22 118.4(13) . . ?
C20 C21 H21 120.8 . . ?
C22 C21 H21 120.8 . . ?
C23 C22 C21 120.2(12) . . ?
C23 C22 H22 119.9 . . ?
C21 C22 H22 119.9 . . ?
C18 C23 C22 117.3(9) . . ?
C18 C23 C24 121.0(8) . . ?
C22 C23 C24 121.2(9) . . ?
O1 C24 C25 123.5(9) . . ?
O1 C24 C23 117.0(9) . . ?
C25 C24 C23 119.5(8) . . ?
C26 C25 C24 121.8(9) . . ?
C26 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
O2 C26 C25 129.6(8) . . ?
O2 C26 C27 113.2(7) . . ?
C25 C26 C27 117.2(7) . . ?
F3 C27 F1 105.8(7) . . ?
F3 C27 F2 105.1(8) . . ?
F1 C27 F2 106.2(8) . . ?
F3 C27 C26 112.5(7) . . ?
F1 C27 C26 115.4(7) . . ?
F2 C27 C26 111.2(7) . . ?
C33 C28 C29 121.2(9) . . ?
C33 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C30 C29 C28 118.8(9) . . ?
C30 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
C31 C30 C29 121.3(9) . . ?
C31 C30 H30 119.4 . . ?
C29 C30 H30 119.4 . . ?
C30 C31 C32 119.8(10) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C33 C32 C31 120.2(9) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C28 C33 C32 118.7(8) . . ?
C28 C33 C34 120.0(8) . . ?
C32 C33 C34 121.2(9) . . ?
O4 C34 C35 122.2(11) . . ?
O4 C34 C33 116.2(10) . . ?
C35 C34 C33 121.5(10) . . ?
C36 C35 C34 122.7(10) . . ?
C36 C35 H35 118.7 . . ?
C34 C35 H35 118.7 . . ?
O3 C36 C35 131.2(12) . . ?
O3 C36 C37 109.9(11) . . ?
C35 C36 C37 118.9(11) . . ?
F4 C37 F5 107.3(8) . . ?
F4 C37 F6 105.0(9) . . ?
F5 C37 F6 106.3(8) . . ?
F4 C37 C36 112.5(8) . . ?
F5 C37 C36 112.4(8) . . ?
F6 C37 C36 112.9(9) . . ?
C43 C38 C39 120.2(9) . . ?
C43 C38 H38 119.9 . . ?
C39 C38 H38 119.9 . . ?
C40 C39 C38 120.0(11) . . ?
C40 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
C39 C40 C41 121.1(10) . . ?
C39 C40 H40 119.4 . . ?
C41 C40 H40 119.4 . . ?
C40 C41 C42 118.7(9) . . ?
C40 C41 H41 120.7 . . ?
C42 C41 H41 120.7 . . ?
C43 C42 C41 121.3(9) . . ?
C43 C42 H42 119.3 . . ?
C41 C42 H42 119.3 . . ?
C38 C43 C42 118.3(8) . . ?
C38 C43 C44 117.9(8) . . ?
C42 C43 C44 123.7(8) . . ?
O5 C44 C45 122.3(9) . . ?
O5 C44 C43 119.4(9) . . ?
C45 C44 C43 118.3(8) . . ?
C46 C45 C44 123.7(8) . . ?
C46 C45 H45 118.2 . . ?
C44 C45 H45 118.2 . . ?
O6 C46 C45 128.0(7) . . ?
O6 C46 C47 113.7(7) . . ?
C45 C46 C47 118.3(7) . . ?
F8 C47 F7 104.2(9) . . ?
F8 C47 F9 102.3(9) . . ?
F7 C47 F9 105.7(8) . . ?
F8 C47 C46 112.7(7) . . ?
F7 C47 C46 114.1(8) . . ?
F9 C47 C46 116.5(7) . . ?
O6 Eu1 O3 137.22(16) . . ?
O6 Eu1 O2 82.75(17) . . ?
O3 Eu1 O2 118.06(17) . . ?
O6 Eu1 O4 77.97(19) . . ?
O3 Eu1 O4 70.62(18) . . ?
O2 Eu1 O4 79.73(17) . . ?
O6 Eu1 O5 70.75(17) . . ?
O3 Eu1 O5 75.44(17) . . ?
O2 Eu1 O5 149.07(17) . . ?
O4 Eu1 O5 79.38(18) . . ?
O6 Eu1 O1 143.48(17) . . ?
O3 Eu1 O1 78.59(16) . . ?
O2 Eu1 O1 70.19(17) . . ?
O4 Eu1 O1 118.85(18) . . ?
O5 Eu1 O1 140.51(17) . . ?
O6 Eu1 N2 76.34(18) . . ?
O3 Eu1 N2 139.92(18) . . ?
O2 Eu1 N2 80.72(18) . . ?
O4 Eu1 N2 149.35(19) . . ?
O5 Eu1 N2 107.21(18) . . ?
O1 Eu1 N2 75.49(18) . . ?
O6 Eu1 N1 111.34(19) . . ?
O3 Eu1 N1 82.47(18) . . ?
O2 Eu1 N1 132.96(18) . . ?
O4 Eu1 N1 145.79(19) . . ?
O5 Eu1 N1 73.57(19) . . ?
O1 Eu1 N1 73.97(18) . . ?
N2 Eu1 N1 61.3(2) . . ?
C5 N1 C1 118.9(7) . . ?
C5 N1 Eu1 121.4(5) . . ?
C1 N1 Eu1 119.2(5) . . ?
C6 N2 C10 119.6(10) . . ?
C6 N2 Eu1 120.1(7) . . ?
C10 N2 Eu1 118.3(7) . . ?
C24 O1 Eu1 138.2(6) . . ?
C26 O2 Eu1 133.4(5) . . ?
C36 O3 Eu1 128.8(7) . . ?
C34 O4 Eu1 137.2(7) . . ?
C44 O5 Eu1 137.8(6) . . ?
C46 O6 Eu1 133.2(4) . . ?

_refine_diff_density_max         0.957
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_S-2
_database_code_depnum_ccdc_archive 'CCDC 2015143'
loop_
_audit_author_name
_audit_author_address
'Xi-Li Li'
;zhengzhou University of Light Industry
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H36 F9 N2 O6 Sm'
_chemical_formula_sum            'C47 H36 F9 N2 O6 Sm'
_chemical_formula_weight         1046.13

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.7328(4)
_cell_length_b                   10.7633(4)
_cell_length_c                   11.2076(4)
_cell_angle_alpha                83.741(3)
_cell_angle_beta                 66.691(4)
_cell_angle_gamma                73.880(4)
_cell_volume                     1142.29(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3641
_cell_measurement_theta_min      3.9400
_cell_measurement_theta_max      22.7150

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             523
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    1.371
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_T_max  0.750
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8264
_diffrn_reflns_av_unetI/netI     0.0603
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.360
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_full        25.100
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.666
_diffrn_reflns_point_group_measured_fraction_full 0.666
_reflns_number_total             5432
_reflns_number_gt                5243
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.334
_reflns_Friedel_fraction_max     0.334
_reflns_Friedel_fraction_full    0.334

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0302P)²] 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_abs_structure_details 
;
 Flack x determined using 1210 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.011(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5432
_refine_ls_number_parameters     588
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.0739
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.022
_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
C12 C -0.1996(17) 0.9376(14) 0.8552(14) 0.060(4) Uani 1 1 d . . . . .
C14 C -0.1696(14) 0.9971(11) 0.6320(12) 0.046(3) Uani 1 1 d . . . . .
C36 C 0.4567(13) 0.8062(10) 0.7180(12) 0.044(3) Uani 1 1 d . . . . .
C2 C 0.1860(8) 1.1464(8) 0.4784(8) 0.049(2) Uani 1 1 d . . . . .
C15 C -0.2348(9) 1.0560(7) 0.5353(9) 0.051(2) Uani 1 1 d . . . . .
C40 C 0.4977(14) 0.8005(13) 0.4967(15) 0.051(4) Uani 1 1 d . . . . .
H40 H 0.4633 0.8186 0.4307 0.061 Uiso 1 1 calc R U . . .
C24 C 0.2666(11) 0.5584(11) 0.6937(12) 0.052(3) Uani 1 1 d . . . . .
C22 C 0.3008(9) 0.6241(8) 0.4692(9) 0.052(2) Uani 1 1 d . . . . .
C39 C 0.6437(9) 0.7402(8) 0.4657(10) 0.058(2) Uani 1 1 d . . . . .
C13 C -0.2502(10) 0.9981(9) 0.7663(10) 0.057(2) Uani 1 1 d . . . . .
H13 H -0.3443 1.0435 0.7952 0.068 Uiso 1 1 calc R U . . .
C3 C 0.0920(12) 1.2394(9) 0.5690(10) 0.064(3) Uani 1 1 d . . . . .
H3 H 0.0727 1.3244 0.5406 0.076 Uiso 1 1 calc R U . . .
C5 C -0.0714(11) 1.3227(9) 0.7931(10) 0.064(3) Uani 1 1 d . . . . .
C35 C 0.3530(9) 0.8444(7) 0.8467(9) 0.053(2) Uani 1 1 d . . . . .
C44 C 0.7475(12) 0.6993(11) 0.3319(13) 0.072(4) Uani 1 1 d . . . . .
H44 H 0.7122 0.7201 0.2619 0.087 Uiso 1 1 calc R U . . .
C38 C 0.6927(10) 0.7150(9) 0.5654(11) 0.063(3) Uani 1 1 d . . . . .
C20 C -0.1499(11) 1.0867(9) 0.4130(9) 0.068(3) Uani 1 1 d . . . . .
H20 H -0.0545 1.0745 0.3927 0.082 Uiso 1 1 calc R U . . .
C19 C -0.2058(12) 1.1358(9) 0.3199(10) 0.075(3) Uani 1 1 d . . . . .
H19 H -0.1484 1.1573 0.2378 0.090 Uiso 1 1 calc R U . . .
C37 C 0.5986(10) 0.7486(9) 0.6902(11) 0.065(3) Uani 1 1 d . . . . .
H37 H 0.6307 0.7324 0.7577 0.078 Uiso 1 1 calc R U . . .
C25 C 0.2924(10) 0.4522(9) 0.7866(10) 0.071(3) Uani 1 1 d . . . . .
C6 C -0.0475(12) 1.4443(9) 0.7767(10) 0.073(3) Uani 1 1 d . . . . .
H6 H 0.0290 1.4610 0.7066 0.088 Uiso 1 1 calc R U . . .
C45 C 0.8344(11) 0.5546(10) 0.3372(11) 0.082(3) Uani 1 1 d . . . . .
C7 C -0.1381(15) 1.5407(10) 0.8652(12) 0.092(4) Uani 1 1 d . . . . .
H7 H -0.1204 1.6217 0.8562 0.110 Uiso 1 1 calc R U . . .
C21 C 0.3680(11) 0.5851(9) 0.3285(10) 0.065(3) Uani 1 1 d . . . . .
C16 C -0.3761(10) 1.0733(9) 0.5640(11) 0.073(3) Uani 1 1 d . . . . .
H16 H -0.4345 1.0530 0.6462 0.088 Uiso 1 1 calc R U . . .
C34 C 0.3873(12) 0.8348(10) 0.9553(11) 0.080(3) Uani 1 1 d . . . . .
H34 H 0.4800 0.8000 0.9468 0.096 Uiso 1 1 calc R U . . .
C23 C 0.3233(13) 0.5311(12) 0.5568(12) 0.071(4) Uani 1 1 d . . . . .
H23 H 0.3764 0.4481 0.5273 0.086 Uiso 1 1 calc R U . . .
C30 C 0.2868(12) 0.4818(10) 0.9032(11) 0.086(3) Uani 1 1 d . . . . .
H30 H 0.2640 0.5683 0.9254 0.104 Uiso 1 1 calc R U . . .
C42 C 0.9193(10) 0.6196(12) 0.3869(13) 0.088(4) Uani 1 1 d . . . . .
H42 H 1.0201 0.5780 0.3569 0.106 Uiso 1 1 calc R U . . .
C10 C -0.1797(13) 1.3009(10) 0.8990(12) 0.099(4) Uani 1 1 d . . . . .
H10 H -0.1916 1.2175 0.9152 0.119 Uiso 1 1 calc R U . . .
C8 C -0.2526(14) 1.5183(12) 0.9649(13) 0.104(4) Uani 1 1 d . . . . .
H8 H -0.3169 1.5855 1.0201 0.125 Uiso 1 1 calc R U . . .
C17 C -0.4309(11) 1.1213(10) 0.4693(12) 0.079(3) Uani 1 1 d . . . . .
H17 H -0.5257 1.1321 0.4878 0.095 Uiso 1 1 calc R U . . .
C33 C 0.2862(14) 0.8758(10) 1.0746(11) 0.086(3) Uani 1 1 d . . . . .
H33 H 0.3093 0.8714 1.1470 0.103 Uiso 1 1 calc R U . . .
C4 C 0.0226(13) 1.2141(11) 0.7029(12) 0.054(3) Uani 1 1 d . . . . .
C26 C 0.3029(15) 0.3238(10) 0.7613(13) 0.116(5) Uani 1 1 d . . . . .
H26 H 0.2993 0.3031 0.6844 0.139 Uiso 1 1 calc R U . . .
C41 C 0.8476(10) 0.6465(12) 0.5303(13) 0.093(4) Uani 1 1 d . . . . .
H41A H 0.8926 0.7002 0.5551 0.111 Uiso 1 1 calc R U . . .
H41B H 0.8562 0.5658 0.5779 0.111 Uiso 1 1 calc R U . . .
C46 C 0.7618(13) 0.4578(9) 0.4251(14) 0.111(5) Uani 1 1 d . . . . .
H46A H 0.6878 0.4500 0.4010 0.167 Uiso 1 1 calc R U . . .
H46B H 0.7230 0.4866 0.5136 0.167 Uiso 1 1 calc R U . . .
H46C H 0.8284 0.3752 0.4165 0.167 Uiso 1 1 calc R U . . .
C11 C -0.2975(10) 0.9430(10) 0.9951(10) 0.064(3) Uani 1 1 d . . . . .
C18 C -0.3450(13) 1.1523(10) 0.3498(12) 0.079(3) Uani 1 1 d . . . . .
H18 H -0.3823 1.1853 0.2873 0.095 Uiso 1 1 calc R U . . .
C43 C 0.8794(11) 0.7413(12) 0.3116(13) 0.106(4) Uani 1 1 d . . . . .
H43A H 0.8610 0.8216 0.3546 0.127 Uiso 1 1 calc R U . . .
H43B H 0.9430 0.7414 0.2215 0.127 Uiso 1 1 calc R U . . .
C1 C 0.2425(11) 1.1862(9) 0.3387(9) 0.057(2) Uani 1 1 d . . . . .
C47 C 0.9225(13) 0.4992(15) 0.1999(14) 0.136(6) Uani 1 1 d . . . . .
H47A H 1.0069 0.4378 0.1997 0.204 Uiso 1 1 calc R U . . .
H47B H 0.9465 0.5680 0.1405 0.204 Uiso 1 1 calc R U . . .
H47C H 0.8695 0.4569 0.1738 0.204 Uiso 1 1 calc R U . . .
C32 C 0.1506(12) 0.9233(10) 1.0844(10) 0.079(3) Uani 1 1 d . . . . .
H32 H 0.0794 0.9500 1.1646 0.095 Uiso 1 1 calc R U . . .
C31 C 0.1197(11) 0.9317(10) 0.9749(10) 0.072(3) Uani 1 1 d . . . . .
H31 H 0.0273 0.9659 0.9825 0.087 Uiso 1 1 calc R U . . .
C9 C -0.2733(15) 1.3987(12) 0.9839(13) 0.123(6) Uani 1 1 d . . . . .
H9 H -0.3502 1.3822 1.0538 0.148 Uiso 1 1 calc R U . . .
C29 C 0.3137(16) 0.3880(16) 0.9903(13) 0.135(6) Uani 1 1 d . U . . .
H29 H 0.3242 0.4099 1.0632 0.162 Uiso 1 1 calc R U . . .
F1 F 0.1940(10) 1.1405(10) 0.2687(6) 0.153(4) Uani 1 1 d . . . . .
F2 F 0.3736(7) 1.1477(10) 0.2823(7) 0.158(4) Uani 1 1 d . . . . .
F3 F 0.2104(11) 1.3069(7) 0.3162(6) 0.170(5) Uani 1 1 d . . . . .
F4 F -0.2455(8) 0.9785(9) 1.0714(7) 0.131(3) Uani 1 1 d . . . . .
F5 F -0.4200(8) 1.0215(10) 1.0221(8) 0.142(4) Uani 1 1 d . . . . .
F6 F -0.3187(8) 0.8327(7) 1.0394(7) 0.125(3) Uani 1 1 d . . . . .
F7 F 0.4556(7) 0.6549(7) 0.2572(6) 0.104(2) Uani 1 1 d . . . . .
F8 F 0.4424(9) 0.4641(6) 0.3022(6) 0.121(3) Uani 1 1 d . . . . .
F9 F 0.2755(7) 0.6037(8) 0.2731(6) 0.110(2) Uani 1 1 d . . . . .
N1 N 0.2183(8) 0.8924(7) 0.8588(7) 0.0575(19) Uani 1 1 d . . . . .
N2 N 0.4109(7) 0.8309(6) 0.6186(7) 0.0455(17) Uani 1 1 d . . . . .
O1 O 0.0405(6) 1.1003(5) 0.7480(6) 0.0590(16) Uani 1 1 d . . . . .
O2 O 0.2306(5) 1.0276(5) 0.4973(5) 0.0541(15) Uani 1 1 d . . . . .
O3 O -0.0719(6) 0.8740(5) 0.8368(5) 0.0519(15) Uani 1 1 d . . . . .
O4 O -0.0379(6) 0.9502(6) 0.5840(6) 0.0600(16) Uani 1 1 d . . . . .
O5 O 0.1971(6) 0.6679(5) 0.7411(5) 0.0538(15) Uani 1 1 d . . . . .
O6 O 0.2319(6) 0.7398(5) 0.4878(5) 0.0531(15) Uani 1 1 d . . . . .
C27 C 0.3187(16) 0.2274(12) 0.8525(15) 0.136(7) Uani 1 1 d . . . . .
H27 H 0.3250 0.1424 0.8366 0.163 Uiso 1 1 calc R U . . .
C28 C 0.3250(19) 0.2587(18) 0.9674(17) 0.158(8) Uani 1 1 d . U . . .
H28 H 0.3365 0.1949 1.0278 0.190 Uiso 1 1 calc R U . . .
Sm1 Sm 0.14400(2) 0.88391(2) 0.66581(2) 0.04496(12) 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
C12 O3 1.295(17) . ?
C12 C13 1.343(17) . ?
C12 C11 1.499(17) . ?
C14 O4 1.267(14) . ?
C14 C13 1.408(16) . ?
C14 C15 1.507(15) . ?
C36 N2 1.360(14) . ?
C36 C37 1.395(15) . ?
C36 C35 1.446(14) . ?
C2 O2 1.261(9) . ?
C2 C3 1.379(12) . ?
C2 C1 1.499(12) . ?
C15 C20 1.378(12) . ?
C15 C16 1.381(12) . ?
C40 N2 1.328(15) . ?
C40 C39 1.432(16) . ?
C40 H40 0.9300 . ?
C24 O5 1.250(11) . ?
C24 C23 1.439(14) . ?
C24 C25 1.503(14) . ?
C22 O6 1.251(9) . ?
C22 C23 1.365(14) . ?
C22 C21 1.503(13) . ?
C39 C38 1.385(13) . ?
C39 C44 1.495(15) . ?
C13 H13 0.9300 . ?
C3 C4 1.421(14) . ?
C3 H3 0.9300 . ?
C5 C10 1.346(14) . ?
C5 C6 1.382(13) . ?
C5 C4 1.484(14) . ?
C35 N1 1.350(10) . ?
C35 C34 1.390(13) . ?
C44 C43 1.528(16) . ?
C44 C45 1.585(14) . ?
C44 H44 0.9800 . ?
C38 C37 1.377(13) . ?
C38 C41 1.525(12) . ?
C20 C19 1.388(13) . ?
C20 H20 0.9300 . ?
C19 C18 1.358(14) . ?
C19 H19 0.9300 . ?
C37 H37 0.9300 . ?
C25 C30 1.353(14) . ?
C25 C26 1.406(15) . ?
C6 C7 1.381(14) . ?
C6 H6 0.9300 . ?
C45 C46 1.512(15) . ?
C45 C47 1.534(16) . ?
C45 C42 1.572(16) . ?
C7 C8 1.355(16) . ?
C7 H7 0.9300 . ?
C21 F8 1.319(10) . ?
C21 F7 1.324(11) . ?
C21 F9 1.327(11) . ?
C16 C17 1.395(13) . ?
C16 H16 0.9300 . ?
C34 C33 1.370(14) . ?
C34 H34 0.9300 . ?
C23 H23 0.9300 . ?
C30 C29 1.379(14) . ?
C30 H30 0.9300 . ?
C42 C41 1.503(16) . ?
C42 C43 1.531(15) . ?
C42 H42 0.9800 . ?
C10 C9 1.378(15) . ?
C10 H10 0.9300 . ?
C8 C9 1.347(16) . ?
C8 H8 0.9300 . ?
C17 C18 1.360(14) . ?
C17 H17 0.9300 . ?
C33 C32 1.365(15) . ?
C33 H33 0.9300 . ?
C4 O1 1.266(12) . ?
C26 C27 1.400(15) . ?
C26 H26 0.9300 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C11 F6 1.280(11) . ?
C11 F5 1.287(11) . ?
C11 F4 1.325(12) . ?
C18 H18 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C1 F2 1.257(11) . ?
C1 F3 1.273(10) . ?
C1 F1 1.295(11) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C32 C31 1.381(13) . ?
C32 H32 0.9300 . ?
C31 N1 1.332(11) . ?
C31 H31 0.9300 . ?
C9 H9 0.9300 . ?
C29 C28 1.41(2) . ?
C29 H29 0.9300 . ?
N1 Sm1 2.602(7) . ?
N2 Sm1 2.602(7) . ?
O1 Sm1 2.393(6) . ?
O2 Sm1 2.365(5) . ?
O3 Sm1 2.373(5) . ?
O4 Sm1 2.379(6) . ?
O5 Sm1 2.379(5) . ?
O6 Sm1 2.377(6) . ?
C27 C28 1.40(2) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?

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
O3 C12 C13 128.1(12) . . ?
O3 C12 C11 113.1(12) . . ?
C13 C12 C11 118.8(13) . . ?
O4 C14 C13 122.9(12) . . ?
O4 C14 C15 115.3(10) . . ?
C13 C14 C15 121.8(11) . . ?
N2 C36 C37 118.8(11) . . ?
N2 C36 C35 116.8(10) . . ?
C37 C36 C35 124.4(11) . . ?
O2 C2 C3 127.8(8) . . ?
O2 C2 C1 113.9(8) . . ?
C3 C2 C1 118.3(8) . . ?
C20 C15 C16 119.3(9) . . ?
C20 C15 C14 119.1(9) . . ?
C16 C15 C14 121.5(10) . . ?
N2 C40 C39 120.7(13) . . ?
N2 C40 H40 119.7 . . ?
C39 C40 H40 119.7 . . ?
O5 C24 C23 123.4(11) . . ?
O5 C24 C25 117.1(10) . . ?
C23 C24 C25 119.6(10) . . ?
O6 C22 C23 129.6(10) . . ?
O6 C22 C21 113.6(8) . . ?
C23 C22 C21 116.9(9) . . ?
C38 C39 C40 118.7(11) . . ?
C38 C39 C44 117.2(9) . . ?
C40 C39 C44 124.1(11) . . ?
C12 C13 C14 124.0(11) . . ?
C12 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
C2 C3 C4 124.4(9) . . ?
C2 C3 H3 117.8 . . ?
C4 C3 H3 117.8 . . ?
C10 C5 C6 118.4(10) . . ?
C10 C5 C4 119.1(10) . . ?
C6 C5 C4 122.4(10) . . ?
N1 C35 C34 119.9(9) . . ?
N1 C35 C36 117.3(9) . . ?
C34 C35 C36 122.8(9) . . ?
C39 C44 C43 107.4(11) . . ?
C39 C44 C45 108.8(9) . . ?
C43 C44 C45 87.7(9) . . ?
C39 C44 H44 116.4 . . ?
C43 C44 H44 116.4 . . ?
C45 C44 H44 116.4 . . ?
C37 C38 C39 118.5(8) . . ?
C37 C38 C41 123.9(10) . . ?
C39 C38 C41 117.6(10) . . ?
C15 C20 C19 120.4(10) . . ?
C15 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C18 C19 C20 119.5(10) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C38 C37 C36 121.7(10) . . ?
C38 C37 H37 119.1 . . ?
C36 C37 H37 119.1 . . ?
C30 C25 C26 119.1(10) . . ?
C30 C25 C24 120.0(10) . . ?
C26 C25 C24 120.3(11) . . ?
C7 C6 C5 119.5(11) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C46 C45 C47 110.7(11) . . ?
C46 C45 C42 117.9(10) . . ?
C47 C45 C42 111.4(10) . . ?
C46 C45 C44 119.8(9) . . ?
C47 C45 C44 110.9(10) . . ?
C42 C45 C44 83.5(9) . . ?
C8 C7 C6 120.6(11) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
F8 C21 F7 104.5(9) . . ?
F8 C21 F9 105.4(9) . . ?
F7 C21 F9 104.1(8) . . ?
F8 C21 C22 116.6(8) . . ?
F7 C21 C22 112.4(8) . . ?
F9 C21 C22 112.8(8) . . ?
C15 C16 C17 119.8(10) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C33 C34 C35 120.8(10) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C22 C23 C24 121.6(11) . . ?
C22 C23 H23 119.2 . . ?
C24 C23 H23 119.2 . . ?
C25 C30 C29 122.3(12) . . ?
C25 C30 H30 118.9 . . ?
C29 C30 H30 118.9 . . ?
C41 C42 C43 109.7(10) . . ?
C41 C42 C45 111.6(9) . . ?
C43 C42 C45 88.1(9) . . ?
C41 C42 H42 114.8 . . ?
C43 C42 H42 114.8 . . ?
C45 C42 H42 114.8 . . ?
C5 C10 C9 121.8(11) . . ?
C5 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C9 C8 C7 120.0(11) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C18 C17 C16 119.7(10) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C32 C33 C34 118.1(11) . . ?
C32 C33 H33 120.9 . . ?
C34 C33 H33 120.9 . . ?
O1 C4 C3 121.4(11) . . ?
O1 C4 C5 118.8(10) . . ?
C3 C4 C5 119.8(9) . . ?
C27 C26 C25 119.5(14) . . ?
C27 C26 H26 120.2 . . ?
C25 C26 H26 120.2 . . ?
C42 C41 C38 110.4(9) . . ?
C42 C41 H41A 109.6 . . ?
C38 C41 H41A 109.6 . . ?
C42 C41 H41B 109.6 . . ?
C38 C41 H41B 109.6 . . ?
H41A C41 H41B 108.1 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
F6 C11 F5 105.9(10) . . ?
F6 C11 F4 104.4(9) . . ?
F5 C11 F4 105.2(10) . . ?
F6 C11 C12 112.9(10) . . ?
F5 C11 C12 115.9(10) . . ?
F4 C11 C12 111.7(10) . . ?
C19 C18 C17 121.3(10) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C44 C43 C42 86.8(8) . . ?
C44 C43 H43A 114.2 . . ?
C42 C43 H43A 114.2 . . ?
C44 C43 H43B 114.2 . . ?
C42 C43 H43B 114.2 . . ?
H43A C43 H43B 111.3 . . ?
F2 C1 F3 106.3(9) . . ?
F2 C1 F1 104.3(9) . . ?
F3 C1 F1 101.9(9) . . ?
F2 C1 C2 114.5(8) . . ?
F3 C1 C2 116.1(8) . . ?
F1 C1 C2 112.4(8) . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C33 C32 C31 119.8(11) . . ?
C33 C32 H32 120.1 . . ?
C31 C32 H32 120.1 . . ?
N1 C31 C32 122.0(10) . . ?
N1 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C8 C9 C10 119.5(11) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
C30 C29 C28 119.0(16) . . ?
C30 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
C31 N1 C35 119.4(9) . . ?
C31 N1 Sm1 119.3(6) . . ?
C35 N1 Sm1 120.9(6) . . ?
C40 N2 C36 121.6(10) . . ?
C40 N2 Sm1 116.3(8) . . ?
C36 N2 Sm1 120.3(7) . . ?
C4 O1 Sm1 137.8(7) . . ?
C2 O2 Sm1 133.1(5) . . ?
C12 O3 Sm1 130.8(7) . . ?
C14 O4 Sm1 135.8(7) . . ?
C24 O5 Sm1 137.8(7) . . ?
C22 O6 Sm1 133.5(5) . . ?
C28 C27 C26 120.1(15) . . ?
C28 C27 H27 120.0 . . ?
C26 C27 H27 120.0 . . ?
C27 C28 C29 119.2(14) . . ?
C27 C28 H28 120.4 . . ?
C29 C28 H28 120.4 . . ?
O2 Sm1 O3 138.12(17) . . ?
O2 Sm1 O6 81.89(19) . . ?
O3 Sm1 O6 117.8(2) . . ?
O2 Sm1 O5 143.28(18) . . ?
O3 Sm1 O5 77.85(18) . . ?
O6 Sm1 O5 71.07(19) . . ?
O2 Sm1 O4 77.8(2) . . ?
O3 Sm1 O4 71.3(2) . . ?
O6 Sm1 O4 78.7(2) . . ?
O5 Sm1 O4 118.8(2) . . ?
O2 Sm1 O1 71.47(19) . . ?
O3 Sm1 O1 75.58(19) . . ?
O6 Sm1 O1 148.53(18) . . ?
O5 Sm1 O1 140.1(2) . . ?
O4 Sm1 O1 79.6(2) . . ?
O2 Sm1 N1 111.9(2) . . ?
O3 Sm1 N1 82.3(2) . . ?
O6 Sm1 N1 133.2(2) . . ?
O5 Sm1 N1 73.3(2) . . ?
O4 Sm1 N1 146.6(2) . . ?
O1 Sm1 N1 74.1(2) . . ?
O2 Sm1 N2 75.37(19) . . ?
O3 Sm1 N2 140.48(19) . . ?
O6 Sm1 N2 80.6(2) . . ?
O5 Sm1 N2 76.06(19) . . ?
O4 Sm1 N2 148.0(2) . . ?
O1 Sm1 N2 107.6(2) . . ?
N1 Sm1 N2 62.0(2) . . ?

_refine_diff_density_max         0.611
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_R-2
_database_code_depnum_ccdc_archive 'CCDC 2015140'
loop_
_audit_author_name
_audit_author_address
'Xi-Li Li'
;zhengzhou University of Light Industry
China
;
_audit_update_record             
;
2020-07-21 deposited with the CCDC.	2020-12-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H36 F9 N2 O6 Sm'
_chemical_formula_sum            'C47 H36 F9 N2 O6 Sm'
_chemical_formula_weight         1046.13

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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_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'

_cell_length_a                   10.6922(7)
_cell_length_b                   10.7184(9)
_cell_length_c                   11.1514(8)
_cell_angle_alpha                83.872(7)
_cell_angle_beta                 66.808(6)
_cell_angle_gamma                74.017(7)
_cell_volume                     1129.30(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    3970
_cell_measurement_theta_min      3.9520
_cell_measurement_theta_max      22.9740

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_F_000             523
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.28
_exptl_absorpt_coefficient_mu    1.387
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65806
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'SADABS; Bruker, 2012'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7953
_diffrn_reflns_av_unetI/netI     0.0549
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.370
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_full        25.099
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.675
_diffrn_reflns_point_group_measured_fraction_full 0.675
_reflns_number_total             5444
_reflns_number_gt                5406
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.352
_reflns_Friedel_fraction_max     0.351
_reflns_Friedel_fraction_full    0.351

_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       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0371P)²] 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_abs_structure_details 
;
 Flack x determined using 1350 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.014(10)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5444
_refine_ls_number_parameters     588
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0770
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.037
_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
C1 C 0.5559(10) -0.0997(9) 1.1650(9) 0.058(2) Uani 1 1 d . . . . .
C2 C 0.6118(8) -0.0586(8) 1.0266(8) 0.047(2) Uani 1 1 d . . . . .
C3 C 0.7050(11) -0.1511(9) 0.9363(10) 0.060(2) Uani 1 1 d . . . . .
H3 H 0.7252 -0.2364 0.9647 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7731(12) -0.1248(11) 0.8012(12) 0.051(3) Uani 1 1 d . . . . .
C5 C 0.8683(11) -0.2343(10) 0.7106(10) 0.063(3) Uani 1 1 d . . . . .
C6 C 0.8459(11) -0.3574(9) 0.7262(10) 0.068(3) Uani 1 1 d . . . . .
H6 H 0.7694 -0.3747 0.7965 0.082 Uiso 1 1 calc R U . . .
C7 C 0.9365(14) -0.4542(10) 0.6380(12) 0.088(4) Uani 1 1 d . . . . .
H7 H 0.9208 -0.5365 0.6475 0.106 Uiso 1 1 calc R U . . .
C8 C 1.0492(14) -0.4282(14) 0.5369(14) 0.104(4) Uani 1 1 d . . . . .
H8 H 1.1110 -0.4933 0.4773 0.125 Uiso 1 1 calc R U . . .
C9 C 1.0721(16) -0.3099(13) 0.5224(14) 0.120(6) Uani 1 1 d . . . . .
H9 H 1.1530 -0.2948 0.4564 0.143 Uiso 1 1 calc R U . . .
C10 C 0.9770(12) -0.2112(11) 0.6043(12) 0.095(4) Uani 1 1 d . . . . .
H10 H 0.9872 -0.1270 0.5865 0.115 Uiso 1 1 calc R U . . .
C11 C 1.0942(9) 0.1432(10) 0.5061(10) 0.060(2) Uani 1 1 d . . . . .
C12 C 0.9929(15) 0.1507(12) 0.6516(13) 0.050(3) Uani 1 1 d . . . . .
C13 C 1.0478(9) 0.0897(10) 0.7398(9) 0.056(2) Uani 1 1 d . . . . .
H13 H 1.1426 0.0457 0.7102 0.068 Uiso 1 1 calc R U . . .
C14 C 0.9654(14) 0.0906(13) 0.8760(14) 0.052(3) Uani 1 1 d . . . . .
C15 C 1.0297(8) 0.0339(8) 0.9703(9) 0.050(2) Uani 1 1 d . . . . .
C16 C 1.1733(10) 0.0154(10) 0.9405(11) 0.071(3) Uani 1 1 d . . . . .
H16 H 1.2315 0.0362 0.8580 0.086 Uiso 1 1 calc R U . . .
C17 C 1.2288(10) -0.0341(11) 1.0346(12) 0.076(3) Uani 1 1 d . . . . .
H17 H 1.3242 -0.0456 1.0151 0.092 Uiso 1 1 calc R U . . .
C18 C 1.1438(12) -0.0661(10) 1.1558(11) 0.075(3) Uani 1 1 d . . . . .
H18 H 1.1812 -0.0985 1.2187 0.090 Uiso 1 1 calc R U . . .
C19 C 1.0033(11) -0.0502(10) 1.1843(10) 0.075(3) Uani 1 1 d . . . . .
H19 H 0.9456 -0.0732 1.2660 0.090 Uiso 1 1 calc R U . . .
C20 C 0.9475(10) 0.0001(10) 1.0911(9) 0.064(3) Uani 1 1 d . . . . .
H20 H 0.8520 0.0111 1.1113 0.076 Uiso 1 1 calc R U . . .
C21 C 0.4294(10) 0.5025(10) 1.1785(10) 0.064(3) Uani 1 1 d . . . . .
C22 C 0.4969(8) 0.4629(8) 1.0338(8) 0.047(2) Uani 1 1 d . . . . .
C23 C 0.4741(11) 0.5567(11) 0.9449(11) 0.060(3) Uani 1 1 d . . . . .
H23 H 0.4207 0.6401 0.9742 0.072 Uiso 1 1 calc R U . . .
C24 C 0.5299(10) 0.5291(10) 0.8109(12) 0.048(2) Uani 1 1 d . . . . .
C25 C 0.5040(10) 0.6365(9) 0.7199(10) 0.069(3) Uani 1 1 d . . . . .
C26 C 0.4962(14) 0.7642(11) 0.7422(14) 0.101(4) Uani 1 1 d . . . . .
H26 H 0.5015 0.7859 0.8183 0.122 Uiso 1 1 calc R U . . .
C27 C 0.4804(16) 0.8603(13) 0.6497(16) 0.126(6) Uani 1 1 d . . . . .
H27 H 0.4765 0.9457 0.6629 0.152 Uiso 1 1 calc R U . . .
C28 C 0.471(2) 0.8250(18) 0.5373(17) 0.145(7) Uani 1 1 d . U . . .
H28 H 0.4550 0.8887 0.4776 0.174 Uiso 1 1 calc R U . . .
C29 C 0.4833(16) 0.6988(16) 0.5131(14) 0.123(5) Uani 1 1 d . U . . .
H29 H 0.4749 0.6764 0.4388 0.148 Uiso 1 1 calc R U . . .
C30 C 0.5089(12) 0.6054(11) 0.6020(10) 0.084(3) Uani 1 1 d . . . . .
H30 H 0.5302 0.5184 0.5810 0.101 Uiso 1 1 calc R U . . .
C31 C 0.6766(10) 0.1549(10) 0.5291(9) 0.065(3) Uani 1 1 d . . . . .
H31 H 0.7696 0.1206 0.5208 0.077 Uiso 1 1 calc R U . . .
C32 C 0.6442(12) 0.1634(10) 0.4197(10) 0.074(3) Uani 1 1 d . . . . .
H32 H 0.7151 0.1365 0.3390 0.088 Uiso 1 1 calc R U . . .
C33 C 0.5093(13) 0.2107(12) 0.4300(11) 0.085(3) Uani 1 1 d . . . . .
H33 H 0.4854 0.2142 0.3578 0.102 Uiso 1 1 calc R U . . .
C34 C 0.4112(11) 0.2524(10) 0.5471(10) 0.069(3) Uani 1 1 d . . . . .
H34 H 0.3188 0.2894 0.5551 0.083 Uiso 1 1 calc R U . . .
C35 C 0.4446(9) 0.2416(8) 0.6574(9) 0.050(2) Uani 1 1 d . . . . .
C36 C 0.3415(14) 0.2799(11) 0.7893(13) 0.048(3) Uani 1 1 d . . . . .
C37 C 0.1977(10) 0.3405(10) 0.8127(12) 0.071(3) Uani 1 1 d . . . . .
H37 H 0.1674 0.3579 0.7436 0.085 Uiso 1 1 calc R U . . .
C38 C 0.1049(9) 0.3728(9) 0.9368(11) 0.066(3) Uani 1 1 d . . . . .
C39 C 0.2954(14) 0.2888(12) 1.0079(16) 0.051(3) Uani 1 1 d . . . . .
H39 H 0.3282 0.2713 1.0753 0.061 Uiso 1 1 calc R U . . .
C40 C 0.1545(9) 0.3478(9) 1.0377(10) 0.057(2) Uani 1 1 d . . . . .
C41 C -0.0502(10) 0.4412(12) 0.9737(13) 0.088(4) Uani 1 1 d . . . . .
H41A H -0.0591 0.5217 0.9252 0.106 Uiso 1 1 calc R U . . .
H41B H -0.0958 0.3868 0.9497 0.106 Uiso 1 1 calc R U . . .
C42 C -0.1230(10) 0.4702(13) 1.1172(14) 0.086(4) Uani 1 1 d . . . . .
H42 H -0.2238 0.5129 1.1469 0.103 Uiso 1 1 calc R U . . .
C43 C -0.0828(11) 0.3480(13) 1.1943(13) 0.100(4) Uani 1 1 d . . . . .
H43A H -0.1469 0.3488 1.2847 0.120 Uiso 1 1 calc R U . . .
H43B H -0.0655 0.2671 1.1518 0.120 Uiso 1 1 calc R U . . .
C44 C 0.0490(11) 0.3874(12) 1.1746(13) 0.072(3) Uani 1 1 d . . . . .
H44 H 0.0841 0.3675 1.2453 0.086 Uiso 1 1 calc R U . . .
C45 C -0.0366(10) 0.5326(12) 1.1654(12) 0.084(4) Uani 1 1 d . . . . .
C46 C 0.0358(14) 0.6296(11) 1.0769(17) 0.119(5) Uani 1 1 d . . . . .
H46A H 0.0777 0.5986 0.9886 0.178 Uiso 1 1 calc R U . . .
H46B H 0.1075 0.6405 1.1031 0.178 Uiso 1 1 calc R U . . .
H46C H -0.0319 0.7114 1.0827 0.178 Uiso 1 1 calc R U . . .
C47 C -0.1247(14) 0.5875(16) 1.3035(15) 0.136(6) Uani 1 1 d . . . . .
H47A H -0.0714 0.6296 1.3302 0.204 Uiso 1 1 calc R U . . .
H47B H -0.1486 0.5181 1.3627 0.204 Uiso 1 1 calc R U . . .
H47C H -0.2093 0.6491 1.3041 0.204 Uiso 1 1 calc R U . . .
F1 F 0.6025(10) -0.0529(11) 1.2348(7) 0.151(4) Uani 1 1 d . . . . .
F2 F 0.4231(7) -0.0597(12) 1.2218(7) 0.163(5) Uani 1 1 d . . . . .
F3 F 0.5859(12) -0.2203(8) 1.1897(7) 0.166(4) Uani 1 1 d . . . . .
F4 F 1.1179(9) 0.2549(8) 0.4643(7) 0.122(3) Uani 1 1 d . . . . .
F5 F 1.2162(8) 0.0663(12) 0.4848(9) 0.142(4) Uani 1 1 d . . . . .
F6 F 1.0414(7) 0.1096(9) 0.4318(6) 0.123(3) Uani 1 1 d . . . . .
F7 F 0.5209(7) 0.4838(8) 1.2318(6) 0.108(2) Uani 1 1 d . . . . .
F8 F 0.3417(7) 0.4317(7) 1.2464(6) 0.101(2) Uani 1 1 d . . . . .
F9 F 0.3546(9) 0.6246(7) 1.2022(7) 0.120(3) Uani 1 1 d . . . . .
N1 N 0.5791(7) 0.1944(7) 0.6460(7) 0.0500(17) Uani 1 1 d . . . . .
N2 N 0.3870(7) 0.2557(6) 0.8858(7) 0.0463(16) Uani 1 1 d . . . . .
O1 O 0.7560(6) -0.0136(6) 0.7559(6) 0.0541(15) Uani 1 1 d . . . . .
O2 O 0.5680(5) 0.0594(5) 1.0064(5) 0.0511(14) Uani 1 1 d . . . . .
O3 O 0.8678(5) 0.2145(5) 0.6671(5) 0.0505(14) Uani 1 1 d . . . . .
O4 O 0.8345(6) 0.1379(6) 0.9202(6) 0.0556(15) Uani 1 1 d . . . . .
O5 O 0.5988(6) 0.4199(5) 0.7652(5) 0.0493(14) Uani 1 1 d . . . . .
O6 O 0.5639(6) 0.3481(5) 1.0183(6) 0.0508(14) Uani 1 1 d . . . . .
Sm1 Sm 0.65280(2) 0.20370(2) 0.83840(2) 0.04278(12) 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
C1 F3 1.271(11) . ?
C1 F2 1.272(11) . ?
C1 F1 1.277(11) . ?
C1 C2 1.486(12) . ?
C2 O2 1.251(9) . ?
C2 C3 1.367(12) . ?
C3 C4 1.428(14) . ?
C3 H3 0.9300 . ?
C4 O1 1.238(12) . ?
C4 C5 1.489(14) . ?
C5 C10 1.352(15) . ?
C5 C6 1.386(14) . ?
C6 C7 1.377(14) . ?
C6 H6 0.9300 . ?
C7 C8 1.360(18) . ?
C7 H7 0.9300 . ?
C8 C9 1.338(18) . ?
C8 H8 0.9300 . ?
C9 C10 1.367(15) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 F5 1.282(11) . ?
C11 F4 1.293(11) . ?
C11 F6 1.295(11) . ?
C11 C12 1.552(16) . ?
C12 O3 1.276(15) . ?
C12 C13 1.357(16) . ?
C13 C14 1.424(17) . ?
C13 H13 0.9300 . ?
C14 O4 1.256(14) . ?
C14 C15 1.466(16) . ?
C15 C20 1.362(13) . ?
C15 C16 1.397(12) . ?
C16 C17 1.391(14) . ?
C16 H16 0.9300 . ?
C17 C18 1.370(15) . ?
C17 H17 0.9300 . ?
C18 C19 1.372(14) . ?
C18 H18 0.9300 . ?
C19 C20 1.385(13) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 F7 1.295(11) . ?
C21 F8 1.318(12) . ?
C21 F9 1.324(11) . ?
C21 C22 1.538(12) . ?
C22 O6 1.233(9) . ?
C22 C23 1.377(14) . ?
C23 C24 1.405(14) . ?
C23 H23 0.9300 . ?
C24 O5 1.236(11) . ?
C24 C25 1.493(15) . ?
C25 C30 1.368(15) . ?
C25 C26 1.391(15) . ?
C26 C27 1.403(18) . ?
C26 H26 0.9300 . ?
C27 C28 1.40(2) . ?
C27 H27 0.9300 . ?
C28 C29 1.37(2) . ?
C28 H28 0.9300 . ?
C29 C30 1.383(17) . ?
C29 H29 0.9300 . ?
C30 H30 0.9300 . ?
C31 N1 1.330(10) . ?
C31 C32 1.382(13) . ?
C31 H31 0.9300 . ?
C32 C33 1.352(14) . ?
C32 H32 0.9300 . ?
C33 C34 1.339(13) . ?
C33 H33 0.9300 . ?
C34 C35 1.394(12) . ?
C34 H34 0.9300 . ?
C35 N1 1.345(10) . ?
C35 C36 1.466(15) . ?
C36 N2 1.321(15) . ?
C36 C37 1.423(15) . ?
C37 C38 1.361(14) . ?
C37 H37 0.9300 . ?
C38 C40 1.395(13) . ?
C38 C41 1.522(12) . ?
C39 N2 1.342(16) . ?
C39 C40 1.380(15) . ?
C39 H39 0.9300 . ?
C40 C44 1.517(16) . ?
C41 C42 1.501(17) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C42 C43 1.542(18) . ?
C42 C45 1.549(16) . ?
C42 H42 0.9800 . ?
C43 C44 1.509(16) . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C44 C45 1.590(16) . ?
C44 H44 0.9800 . ?
C45 C46 1.508(18) . ?
C45 C47 1.533(17) . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
N1 Sm1 2.580(7) . ?
N2 Sm1 2.584(6) . ?
O1 Sm1 2.394(6) . ?
O2 Sm1 2.354(6) . ?
O3 Sm1 2.364(5) . ?
O4 Sm1 2.368(6) . ?
O5 Sm1 2.367(5) . ?
O6 Sm1 2.382(5) . ?

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
F3 C1 F2 105.8(10) . . ?
F3 C1 F1 102.4(10) . . ?
F2 C1 F1 103.5(9) . . ?
F3 C1 C2 117.9(8) . . ?
F2 C1 C2 114.0(8) . . ?
F1 C1 C2 111.8(8) . . ?
O2 C2 C3 127.2(8) . . ?
O2 C2 C1 115.1(8) . . ?
C3 C2 C1 117.6(8) . . ?
C2 C3 C4 124.0(9) . . ?
C2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
O1 C4 C3 122.3(10) . . ?
O1 C4 C5 118.4(11) . . ?
C3 C4 C5 119.3(10) . . ?
C10 C5 C6 118.2(10) . . ?
C10 C5 C4 118.8(10) . . ?
C6 C5 C4 122.9(10) . . ?
C7 C6 C5 120.2(11) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 119.3(11) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C7 120.7(12) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.1(12) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 120.9(12) . . ?
C5 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
F5 C11 F4 104.9(10) . . ?
F5 C11 F6 108.8(9) . . ?
F4 C11 F6 106.1(10) . . ?
F5 C11 C12 113.7(10) . . ?
F4 C11 C12 111.1(9) . . ?
F6 C11 C12 111.8(9) . . ?
O3 C12 C13 130.7(11) . . ?
O3 C12 C11 112.0(11) . . ?
C13 C12 C11 117.3(11) . . ?
C12 C13 C14 122.4(10) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
O4 C14 C13 121.5(12) . . ?
O4 C14 C15 117.2(11) . . ?
C13 C14 C15 121.3(11) . . ?
C20 C15 C16 118.8(9) . . ?
C20 C15 C14 119.5(9) . . ?
C16 C15 C14 121.7(10) . . ?
C17 C16 C15 119.8(10) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C18 C17 C16 120.3(9) . . ?
C18 C17 H17 119.8 . . ?
C16 C17 H17 119.8 . . ?
C17 C18 C19 119.9(10) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C20 119.9(10) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 121.3(9) . . ?
C15 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
F7 C21 F8 105.7(9) . . ?
F7 C21 F9 106.9(9) . . ?
F8 C21 F9 105.5(8) . . ?
F7 C21 C22 112.7(7) . . ?
F8 C21 C22 110.5(8) . . ?
F9 C21 C22 115.0(9) . . ?
O6 C22 C23 130.9(9) . . ?
O6 C22 C21 111.8(8) . . ?
C23 C22 C21 117.3(9) . . ?
C22 C23 C24 121.3(10) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
O5 C24 C23 123.0(11) . . ?
O5 C24 C25 118.7(10) . . ?
C23 C24 C25 118.3(9) . . ?
C30 C25 C26 118.7(11) . . ?
C30 C25 C24 118.5(10) . . ?
C26 C25 C24 122.1(11) . . ?
C25 C26 C27 119.9(14) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 118.6(15) . . ?
C28 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?
C29 C28 C27 121.5(16) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 118.2(16) . . ?
C28 C29 H29 120.9 . . ?
C30 C29 H29 120.9 . . ?
C25 C30 C29 122.3(12) . . ?
C25 C30 H30 118.8 . . ?
C29 C30 H30 118.8 . . ?
N1 C31 C32 122.1(9) . . ?
N1 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C33 C32 C31 120.0(10) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 118.1(10) . . ?
C34 C33 H33 121.0 . . ?
C32 C33 H33 121.0 . . ?
C33 C34 C35 121.5(9) . . ?
C33 C34 H34 119.3 . . ?
C35 C34 H34 119.3 . . ?
N1 C35 C34 119.9(8) . . ?
N1 C35 C36 115.8(8) . . ?
C34 C35 C36 124.3(9) . . ?
N2 C36 C37 121.2(11) . . ?
N2 C36 C35 117.6(10) . . ?
C37 C36 C35 121.3(11) . . ?
C38 C37 C36 119.5(10) . . ?
C38 C37 H37 120.3 . . ?
C36 C37 H37 120.3 . . ?
C37 C38 C40 118.8(8) . . ?
C37 C38 C41 124.4(10) . . ?
C40 C38 C41 116.8(10) . . ?
N2 C39 C40 122.8(13) . . ?
N2 C39 H39 118.6 . . ?
C40 C39 H39 118.6 . . ?
C39 C40 C38 118.6(11) . . ?
C39 C40 C44 123.9(11) . . ?
C38 C40 C44 117.5(8) . . ?
C42 C41 C38 111.7(10) . . ?
C42 C41 H41A 109.3 . . ?
C38 C41 H41A 109.3 . . ?
C42 C41 H41B 109.3 . . ?
C38 C41 H41B 109.3 . . ?
H41A C41 H41B 107.9 . . ?
C41 C42 C43 109.3(10) . . ?
C41 C42 C45 111.1(9) . . ?
C43 C42 C45 87.2(10) . . ?
C41 C42 H42 115.3 . . ?
C43 C42 H42 115.3 . . ?
C45 C42 H42 115.3 . . ?
C44 C43 C42 87.9(9) . . ?
C44 C43 H43A 114.0 . . ?
C42 C43 H43A 114.0 . . ?
C44 C43 H43B 114.0 . . ?
C42 C43 H43B 114.0 . . ?
H43A C43 H43B 111.2 . . ?
C43 C44 C40 108.0(11) . . ?
C43 C44 C45 86.8(9) . . ?
C40 C44 C45 106.6(10) . . ?
C43 C44 H44 117.0 . . ?
C40 C44 H44 117.0 . . ?
C45 C44 H44 117.0 . . ?
C46 C45 C47 111.2(11) . . ?
C46 C45 C42 117.6(12) . . ?
C47 C45 C42 110.5(10) . . ?
C46 C45 C44 120.8(9) . . ?
C47 C45 C44 109.2(11) . . ?
C42 C45 C44 84.9(9) . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C45 C47 H47A 109.5 . . ?
C45 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C45 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C31 N1 C35 118.5(7) . . ?
C31 N1 Sm1 119.9(6) . . ?
C35 N1 Sm1 121.2(5) . . ?
C36 N2 C39 119.2(10) . . ?
C36 N2 Sm1 120.5(7) . . ?
C39 N2 Sm1 118.3(7) . . ?
C4 O1 Sm1 137.3(7) . . ?
C2 O2 Sm1 134.0(5) . . ?
C12 O3 Sm1 129.3(7) . . ?
C14 O4 Sm1 137.6(7) . . ?
C24 O5 Sm1 139.1(7) . . ?
C22 O6 Sm1 132.0(5) . . ?
O2 Sm1 O3 137.97(18) . . ?
O2 Sm1 O5 143.20(18) . . ?
O3 Sm1 O5 78.01(19) . . ?
O2 Sm1 O4 77.5(2) . . ?
O3 Sm1 O4 71.50(19) . . ?
O5 Sm1 O4 118.7(2) . . ?
O2 Sm1 O6 81.7(2) . . ?
O3 Sm1 O6 118.1(2) . . ?
O5 Sm1 O6 70.77(19) . . ?
O4 Sm1 O6 78.79(19) . . ?
O2 Sm1 O1 71.16(19) . . ?
O3 Sm1 O1 75.83(19) . . ?
O5 Sm1 O1 140.6(2) . . ?
O4 Sm1 O1 79.6(2) . . ?
O6 Sm1 O1 148.34(19) . . ?
O2 Sm1 N1 112.0(2) . . ?
O3 Sm1 N1 82.2(2) . . ?
O5 Sm1 N1 73.8(2) . . ?
O4 Sm1 N1 146.45(19) . . ?
O6 Sm1 N1 133.30(19) . . ?
O1 Sm1 N1 73.9(2) . . ?
O2 Sm1 N2 75.59(19) . . ?
O3 Sm1 N2 140.40(19) . . ?
O5 Sm1 N2 76.1(2) . . ?
O4 Sm1 N2 147.9(2) . . ?
O6 Sm1 N2 80.4(2) . . ?
O1 Sm1 N2 107.4(2) . . ?
N1 Sm1 N2 62.2(2) . . ?

_refine_diff_density_max         0.670
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.070

