# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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. 
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data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 798521'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2016-12-21 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         'C23 H15 Tb F18 N4 O6'
_chemical_formula_sum            'C23 H15 F18 N4 O6 Tb'
_chemical_formula_weight         944.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1720 4.1540 '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                   20.173(4)
_cell_length_b                   10.666(2)
_cell_length_c                   18.074(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.82(3)
_cell_angle_gamma                90
_cell_volume                     3557.6(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    6491
_cell_measurement_theta_min      2.0476
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_F_000             1824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.167
_exptl_absorpt_coefficient_mu    2.122
_shelx_estimated_absorpt_T_min   0.676
_shelx_estimated_absorpt_T_max   0.676
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.661
_exptl_absorpt_correction_T_max  0.7020
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13681
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.205
_diffrn_reflns_theta_max         25.005
_diffrn_reflns_theta_full        25.005
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3136
_reflns_number_gt                2844
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL-2014/7
_computing_publication_material  SHELXL-2014/7
_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)+(0.0760P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0097(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3129
_refine_ls_number_parameters     322
_refine_ls_number_restraints     220
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.125
_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
Tb1 Tb 1.0000 0.55155(2) 0.2500 0.0529(2) Uani 1 2 d S T P . .
F1 F 0.7285(10) 0.690(2) 0.0688(11) 0.187(6) Uani 0.518(15) 1 d . U P A 1
F2 F 0.7709(10) 0.7704(15) 0.1862(15) 0.202(7) Uani 0.518(15) 1 d D U P A 1
F3 F 0.7012(8) 0.6160(17) 0.1648(15) 0.183(5) Uani 0.518(15) 1 d D U P A 1
F1' F 0.6905(8) 0.598(2) 0.1051(16) 0.187(6) Uani 0.482(15) 1 d . U P A 2
F2' F 0.7636(11) 0.7608(18) 0.1094(16) 0.186(6) Uani 0.482(15) 1 d D U P A 2
F3' F 0.7640(11) 0.711(2) 0.2198(10) 0.200(6) Uani 0.482(15) 1 d D U P A 2
F4 F 0.7672(4) 0.2007(10) 0.1322(9) 0.172(4) Uani 0.736(13) 1 d D U P B 3
F5 F 0.8789(6) 0.1462(9) 0.1958(7) 0.154(4) Uani 0.736(13) 1 d D U P B 3
F6 F 0.8406(7) 0.1960(9) 0.0726(6) 0.165(4) Uani 0.736(13) 1 d D U P B 3
F4' F 0.7742(13) 0.207(3) 0.0773(16) 0.163(7) Uani 0.264(13) 1 d D U P B 4
F5' F 0.8464(17) 0.156(3) 0.2072(14) 0.149(7) Uani 0.264(13) 1 d D U P B 4
F6' F 0.8818(14) 0.162(2) 0.119(2) 0.151(6) Uani 0.264(13) 1 d D U P B 4
F7 F 1.0424(11) 0.8661(10) 0.0766(10) 0.141(4) Uani 0.61(2) 1 d D U P C 5
F8 F 1.0393(11) 1.0331(11) 0.1384(10) 0.127(4) Uani 0.61(2) 1 d D U P C 5
F9 F 0.9404(7) 0.9266(17) 0.0586(8) 0.155(5) Uani 0.61(2) 1 d D U P C 5
F7' F 0.9606(14) 0.901(2) 0.0422(8) 0.147(6) Uani 0.39(2) 1 d D U P C 6
F8' F 1.0753(10) 0.891(2) 0.1191(18) 0.155(5) Uani 0.39(2) 1 d D U P C 6
F9' F 0.9972(19) 1.0423(10) 0.1235(14) 0.123(6) Uani 0.39(2) 1 d D U P C 6
C1 C 0.7548(5) 0.6612(11) 0.1478(7) 0.146(4) Uani 1 1 d D . . . .
C2 C 0.8182(4) 0.5688(9) 0.1662(5) 0.097(2) Uani 1 1 d . . . . .
C3 C 0.8038(4) 0.4443(8) 0.1553(6) 0.104(3) Uani 1 1 d . . . . .
H3 H 0.7567 0.4164 0.1415 0.125 Uiso 1 1 calc R U . . .
C4 C 0.8572(3) 0.3585(6) 0.1641(3) 0.0786(16) Uani 1 1 d . . . . .
C5 C 0.8352(4) 0.2239(8) 0.1417(5) 0.121(3) Uani 1 1 d D . . . .
C6 C 1.0087(5) 0.9215(6) 0.1163(5) 0.119(3) Uani 1 1 d D . . . .
C7 C 1.0040(4) 0.8430(5) 0.1850(3) 0.0777(15) Uani 1 1 d . . . . .
C8 C 1.0000 0.9053(8) 0.2500 0.095(3) Uani 1 2 d S T P . .
H8 H 1.0000 0.9925 0.2500 0.114 Uiso 1 2 calc R U P . .
C9 C 0.9250(3) 0.5358(5) 0.3908(4) 0.0671(14) Uani 1 1 d . . . . .
H9 H 0.9164 0.6217 0.3858 0.080 Uiso 1 1 calc R U . . .
C10 C 0.9268(3) 0.3425(6) 0.4288(4) 0.0794(16) Uani 1 1 d . . . . .
H10 H 0.9202 0.2703 0.4538 0.095 Uiso 1 1 calc R U . . .
C11 C 0.9606(3) 0.3516(5) 0.3794(4) 0.0751(14) Uani 1 1 d . . . . .
H11 H 0.9818 0.2850 0.3637 0.090 Uiso 1 1 calc R U . . .
C12 C 0.8622(4) 0.4961(10) 0.4825(4) 0.1039(19) Uani 1 1 d . . . . .
H12A H 0.8641 0.5854 0.4895 0.156 Uiso 1 1 calc R U . . .
H12B H 0.8826 0.4561 0.5345 0.156 Uiso 1 1 calc R U . . .
H12C H 0.8127 0.4702 0.4543 0.156 Uiso 1 1 calc R U . . .
N1 N 0.9597(3) 0.4745(4) 0.3546(3) 0.0633(10) Uani 1 1 d . . . . .
N2 N 0.9037(3) 0.4604(5) 0.4355(3) 0.0715(13) Uani 1 1 d . . . . .
O1 O 0.8790(2) 0.6214(4) 0.1900(3) 0.0829(11) Uani 1 1 d . . . . .
O2 O 0.92353(17) 0.3788(3) 0.1878(2) 0.0666(9) Uani 1 1 d . . . . .
O3 O 1.0026(2) 0.7284(3) 0.1733(2) 0.0749(10) 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
Tb1 O3 2.354(3) . ?
Tb1 O3 2.354(3) 2_755 ?
Tb1 O1 2.356(4) . ?
Tb1 O1 2.356(4) 2_755 ?
Tb1 O2 2.374(3) 2_755 ?
Tb1 O2 2.374(3) . ?
Tb1 N1 2.481(4) . ?
Tb1 N1 2.481(4) 2_755 ?
F1 C1 1.34(2) . ?
F2 C1 1.327(10) . ?
F3 C1 1.328(9) . ?
F1' C1 1.39(2) . ?
F2' C1 1.320(10) . ?
F3' C1 1.347(10) . ?
F4 C5 1.337(8) . ?
F5 C5 1.313(8) . ?
F6 C5 1.331(8) . ?
F4' C5 1.322(10) . ?
F5' C5 1.328(10) . ?
F6' C5 1.342(10) . ?
F7 C6 1.311(9) . ?
F8 C6 1.326(8) . ?
F9 C6 1.352(9) . ?
F7' C6 1.317(10) . ?
F8' C6 1.362(10) . ?
F9' C6 1.325(9) . ?
C1 C2 1.541(11) . ?
C2 O1 1.255(9) . ?
C2 C3 1.357(9) . ?
C3 C4 1.373(10) . ?
C3 H3 0.9300 . ?
C4 O2 1.248(6) . ?
C4 C5 1.508(10) . ?
C6 C7 1.533(9) . ?
C7 O3 1.239(6) . ?
C7 C8 1.380(7) . ?
C8 C7 1.380(7) 2_755 ?
C8 H8 0.9300 . ?
C9 N1 1.309(7) . ?
C9 N2 1.329(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.329(8) . ?
C10 N2 1.363(8) . ?
C10 H10 0.9300 . ?
C11 N1 1.383(6) . ?
C11 H11 0.9300 . ?
C12 N2 1.462(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 Tb1 O3 73.49(16) . 2_755 ?
O3 Tb1 O1 74.98(15) . . ?
O3 Tb1 O1 75.67(15) 2_755 . ?
O3 Tb1 O1 75.67(15) . 2_755 ?
O3 Tb1 O1 74.98(15) 2_755 2_755 ?
O1 Tb1 O1 143.1(2) . 2_755 ?
O3 Tb1 O2 137.39(13) . 2_755 ?
O3 Tb1 O2 120.50(13) 2_755 2_755 ?
O1 Tb1 O2 144.84(14) . 2_755 ?
O1 Tb1 O2 70.92(13) 2_755 2_755 ?
O3 Tb1 O2 120.50(13) . . ?
O3 Tb1 O2 137.39(13) 2_755 . ?
O1 Tb1 O2 70.92(13) . . ?
O1 Tb1 O2 144.84(14) 2_755 . ?
O2 Tb1 O2 78.22(16) 2_755 . ?
O3 Tb1 N1 143.75(14) . . ?
O3 Tb1 N1 74.01(13) 2_755 . ?
O1 Tb1 N1 81.83(15) . . ?
O1 Tb1 N1 110.58(15) 2_755 . ?
O2 Tb1 N1 74.47(14) 2_755 . ?
O2 Tb1 N1 75.73(14) . . ?
O3 Tb1 N1 74.01(13) . 2_755 ?
O3 Tb1 N1 143.75(14) 2_755 2_755 ?
O1 Tb1 N1 110.58(15) . 2_755 ?
O1 Tb1 N1 81.83(15) 2_755 2_755 ?
O2 Tb1 N1 75.73(14) 2_755 2_755 ?
O2 Tb1 N1 74.48(14) . 2_755 ?
N1 Tb1 N1 141.3(2) . 2_755 ?
F2 C1 F3 104.4(17) . . ?
F2 C1 F1 105.0(15) . . ?
F3 C1 F1 108.7(14) . . ?
F2' C1 F3' 101.3(17) . . ?
F2' C1 F1' 113.0(16) . . ?
F3' C1 F1' 117.4(16) . . ?
F2' C1 C2 110.6(10) . . ?
F2 C1 C2 116.3(11) . . ?
F3 C1 C2 113.7(10) . . ?
F1 C1 C2 108.4(11) . . ?
F3' C1 C2 105.4(12) . . ?
F1' C1 C2 108.7(11) . . ?
O1 C2 C3 127.5(7) . . ?
O1 C2 C1 113.5(8) . . ?
C3 C2 C1 119.0(8) . . ?
C2 C3 C4 121.6(7) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
O2 C4 C3 127.3(6) . . ?
O2 C4 C5 114.6(6) . . ?
C3 C4 C5 118.1(6) . . ?
F4' C5 F5' 118(2) . . ?
F5 C5 F6 105.8(10) . . ?
F5 C5 F4 108.9(9) . . ?
F6 C5 F4 107.9(9) . . ?
F4' C5 F6' 100(2) . . ?
F5' C5 F6' 97(2) . . ?
F5 C5 C4 111.4(7) . . ?
F4' C5 C4 115.9(15) . . ?
F5' C5 C4 110.8(17) . . ?
F6 C5 C4 109.8(7) . . ?
F4 C5 C4 112.7(8) . . ?
F6' C5 C4 112.6(11) . . ?
F7' C6 F9' 100.2(15) . . ?
F7 C6 F8 106.8(10) . . ?
F7 C6 F9 100.9(10) . . ?
F8 C6 F9 113.6(13) . . ?
F7' C6 F8' 108.0(14) . . ?
F9' C6 F8' 115.7(16) . . ?
F7 C6 C7 114.4(7) . . ?
F7' C6 C7 118.1(12) . . ?
F9' C6 C7 112.4(12) . . ?
F8 C6 C7 114.8(9) . . ?
F9 C6 C7 105.7(9) . . ?
F8' C6 C7 102.9(10) . . ?
O3 C7 C8 128.0(5) . . ?
O3 C7 C6 113.9(5) . . ?
C8 C7 C6 118.1(5) . . ?
C7 C8 C7 122.4(8) 2_755 . ?
C7 C8 H8 118.8 2_755 . ?
C7 C8 H8 118.8 . . ?
N1 C9 N2 111.8(5) . . ?
N1 C9 H9 124.1 . . ?
N2 C9 H9 124.1 . . ?
C11 C10 N2 106.2(5) . . ?
C11 C10 H10 126.9 . . ?
N2 C10 H10 126.9 . . ?
C10 C11 N1 110.0(5) . . ?
C10 C11 H11 125.0 . . ?
N1 C11 H11 125.0 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 N1 C11 104.6(4) . . ?
C9 N1 Tb1 128.4(3) . . ?
C11 N1 Tb1 126.5(4) . . ?
C9 N2 C10 107.3(5) . . ?
C9 N2 C12 126.7(6) . . ?
C10 N2 C12 126.0(6) . . ?
C2 O1 Tb1 134.7(4) . . ?
C4 O2 Tb1 134.3(4) . . ?
C7 O3 Tb1 134.0(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
F2' C1 C2 O1 41.8(19) . . . . ?
F2 C1 C2 O1 -25(2) . . . . ?
F3 C1 C2 O1 -146.0(14) . . . . ?
F1 C1 C2 O1 93.1(15) . . . . ?
F3' C1 C2 O1 -66.9(17) . . . . ?
F1' C1 C2 O1 166.4(14) . . . . ?
F2' C1 C2 C3 -137.9(17) . . . . ?
F2 C1 C2 C3 155.5(19) . . . . ?
F3 C1 C2 C3 34.3(18) . . . . ?
F1 C1 C2 C3 -86.6(16) . . . . ?
F3' C1 C2 C3 113.4(17) . . . . ?
F1' C1 C2 C3 -13.3(19) . . . . ?
O1 C2 C3 C4 -5.1(16) . . . . ?
C1 C2 C3 C4 174.5(8) . . . . ?
C2 C3 C4 O2 5.4(14) . . . . ?
C2 C3 C4 C5 -173.2(8) . . . . ?
O2 C4 C5 F5 44.8(11) . . . . ?
C3 C4 C5 F5 -136.4(11) . . . . ?
O2 C4 C5 F4' -141(2) . . . . ?
C3 C4 C5 F4' 38(2) . . . . ?
O2 C4 C5 F5' 81.2(18) . . . . ?
C3 C4 C5 F5' -100.1(18) . . . . ?
O2 C4 C5 F6 -72.1(9) . . . . ?
C3 C4 C5 F6 106.7(10) . . . . ?
O2 C4 C5 F4 167.6(8) . . . . ?
C3 C4 C5 F4 -13.6(12) . . . . ?
O2 C4 C5 F6' -26(2) . . . . ?
C3 C4 C5 F6' 152.8(19) . . . . ?
F7 C6 C7 O3 -29.7(13) . . . . ?
F7' C6 C7 O3 52.9(17) . . . . ?
F9' C6 C7 O3 168.8(18) . . . . ?
F8 C6 C7 O3 -153.6(13) . . . . ?
F9 C6 C7 O3 80.4(11) . . . . ?
F8' C6 C7 O3 -66.0(15) . . . . ?
F7 C6 C7 C8 152.0(11) . . . . ?
F7' C6 C7 C8 -125.5(16) . . . . ?
F9' C6 C7 C8 -9.5(19) . . . . ?
F8 C6 C7 C8 28.1(15) . . . . ?
F9 C6 C7 C8 -97.9(10) . . . . ?
F8' C6 C7 C8 115.6(15) . . . . ?
O3 C7 C8 C7 2.2(5) . . . 2_755 ?
C6 C7 C8 C7 -179.7(7) . . . 2_755 ?
N2 C10 C11 N1 0.3(7) . . . . ?
N2 C9 N1 C11 -0.6(7) . . . . ?
N2 C9 N1 Tb1 171.6(4) . . . . ?
C10 C11 N1 C9 0.2(7) . . . . ?
C10 C11 N1 Tb1 -172.2(4) . . . . ?
N1 C9 N2 C10 0.8(7) . . . . ?
N1 C9 N2 C12 -178.4(6) . . . . ?
C11 C10 N2 C9 -0.7(7) . . . . ?
C11 C10 N2 C12 178.6(6) . . . . ?
C3 C2 O1 Tb1 -12.9(14) . . . . ?
C1 C2 O1 Tb1 167.4(6) . . . . ?
C3 C4 O2 Tb1 12.1(10) . . . . ?
C5 C4 O2 Tb1 -169.3(5) . . . . ?
C8 C7 O3 Tb1 -4.4(10) . . . . ?
C6 C7 O3 Tb1 177.5(5) . . . . ?

_refine_diff_density_max         2.165
_refine_diff_density_min         -0.897
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_r101025c
_database_code_depnum_ccdc_archive 'CCDC 800739'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2016-12-21 downloaded from the CCDC.
;
_audit_creation_date             2016-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H15 Dy F18 N4 O6'
_chemical_formula_sum            'C23 H15 Dy F18 N4 O6'
_chemical_formula_weight         947.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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'
Dy Dy -0.1890 4.4100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   20.103(4)
_cell_length_b                   10.649(2)
_cell_length_c                   18.062(4)
_cell_angle_alpha                90
_cell_angle_beta                 113.88(3)
_cell_angle_gamma                90
_cell_volume                     3535.7(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5549
_cell_measurement_temperature    113.1500
_cell_measurement_theta_max      27.9064
_cell_measurement_theta_min      2.2102
_shelx_estimated_absorpt_T_max   0.715
_shelx_estimated_absorpt_T_min   0.662
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5190
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.781
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Prism
_exptl_crystal_F_000             1828
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_av_unetI/netI     0.0540
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14331
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.100
_diffrn_reflns_theta_max         25.099
_diffrn_reflns_theta_min         2.210
_diffrn_ambient_temperature      113.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
scan:
	Number of images: 90
	           Slice: -110.0000 - 70.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 0.0000
	             XTD: 44.9977
	          2theta: -19.9451
scan:
	Number of images: 70
	           Slice: -110.0000 - 30.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 44.9977
	          2theta: -19.9451
scan:
	Number of images: 60
	           Slice: -110.0000 - 10.0000
	     Image width: 2.0000
	        Exp time: 3.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 180.0000
	             XTD: 44.9977
	          2theta: -19.9451
;
_diffrn_measurement_device       
;
Saturn70 (4x4 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       dtprofit.ref
_diffrn_number_total             4438
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.0490
_diffrn_orient_matrix_UB_12      0.0224
_diffrn_orient_matrix_UB_13      -0.0075
_diffrn_orient_matrix_UB_21      -0.0408
_diffrn_orient_matrix_UB_22      -0.0809
_diffrn_orient_matrix_UB_23      0.0247
_diffrn_orient_matrix_UB_31      -0.0227
_diffrn_orient_matrix_UB_32      0.0265
_diffrn_orient_matrix_UB_33      0.0495
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           16.0000
_diffrn_source_power             0.8000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2705
_reflns_number_total             3151
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
????
;
_refine_diff_density_max         2.098
_refine_diff_density_min         -0.944
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       0.0041(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     322
_refine_ls_number_reflns         3147
_refine_ls_number_restraints     151
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0604P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0987
_refine_ls_wR_factor_ref         0.1032
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F7-F8 = F7-F9 = F8-F9 = F7'-F8' = F8'-F9' = F7'-F9'
 2.13 with sigma of 0.01
 C6-F7 = C6-F8 = C6-F9 = C6-F7' = C6-F8' = C6-F9'
 1.34 with sigma of 0.01
 F4-F5 = F4-F6 = F5-F6 = F4'-F5' = F4'-F6' = F5'-F6'
 2.13 with sigma of 0.01
 C5-F4 = C5-F5 = C5-F6 = C5-F4' = C5-F5' = C5-F6'
 1.34 with sigma of 0.01
 F1-F2 = F1-F3 = F2-F3 = F1'-F2' = F1'-F3' = F2'-F3'
 2.13 with sigma of 0.01
 C1-F1 = C1-F2 = C1-F3 = C1-F1' = C1-F2' = C1-F3'
 1.34 with sigma of 0.01
3. Rigid bond restraints
 C4, C5
 with sigma for 1-2 distances of 0.02 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1') \\sim
Ueq, Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F4') \\sim
Ueq, Uanis(F5') \\sim Ueq, Uanis(F6') \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq, Uanis(F7') \\sim
Ueq, Uanis(F8') \\sim Ueq, Uanis(F9') \\sim Ueq: with sigma of 0.01 and sigma
for terminal atoms of 0.02
Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Sof(F1')=Sof(F2')=Sof(F3')=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4')=Sof(F5')=Sof(F6')=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
 Sof(F7')=Sof(F8')=Sof(F9')=1-FVAR(3)
 Sof(F7)=Sof(F8)=Sof(F9)=FVAR(3)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C9(H9), C10(H10), C11(H11)
6.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.1633(4) 0.7762(7) 0.3575(5) 0.121(3) Uani 1 1 d D . . . .
C2 C 0.1427(3) 0.6405(6) 0.3359(3) 0.0765(17) Uani 1 1 d . . . . .
C3 C 0.1961(4) 0.5549(8) 0.3446(6) 0.100(3) Uani 1 1 d . . . . .
H3 H 0.2435 0.5827 0.3582 0.120 Uiso 1 1 calc R . . . .
C4 C 0.1816(4) 0.4309(9) 0.3340(5) 0.096(3) Uani 1 1 d . U . . .
C5 C 0.2438(5) 0.3385(9) 0.3514(5) 0.148(4) Uani 1 1 d D U . . .
C6 C -0.0089(5) 0.0796(6) 0.3824(4) 0.121(3) Uani 1 1 d D . . . .
C7 C -0.0036(4) 0.1574(5) 0.3150(3) 0.0767(16) Uani 1 1 d . . . . .
C8 C 0.0000 0.0949(8) 0.2500 0.092(3) Uani 1 2 d S T P . .
H8 H 0.0000 0.0076 0.2500 0.110 Uiso 1 2 calc RS T P . .
C9 C 0.0750(3) 0.4637(6) 0.1094(3) 0.0682(15) Uani 1 1 d . . . . .
H9 H 0.0838 0.3777 0.1142 0.082 Uiso 1 1 calc R . . . .
C10 C 0.0389(3) 0.6473(5) 0.1212(4) 0.0737(15) Uani 1 1 d . . . . .
H10 H 0.0175 0.7139 0.1368 0.088 Uiso 1 1 calc R . . . .
C11 C 0.0732(3) 0.6557(7) 0.0713(4) 0.0785(17) Uani 1 1 d . . . . .
H11 H 0.0797 0.7280 0.0462 0.094 Uiso 1 1 calc R . . . .
C12 C 0.1376(4) 0.5026(9) 0.0176(4) 0.103(2) Uani 1 1 d . . . . .
H12A H 0.1874 0.5280 0.0457 0.155 Uiso 1 1 calc GR . . . .
H12B H 0.1172 0.5425 -0.0345 0.155 Uiso 1 1 calc GR . . . .
H12C H 0.1353 0.4131 0.0107 0.155 Uiso 1 1 calc GR . . . .
Dy1 Dy 0.0000 0.44794(3) 0.2500 0.05207(19) Uani 1 2 d S T P . .
F1 F 0.1257(5) 0.8529(6) 0.2989(5) 0.156(4) Uani 0.835(14) 1 d D U . A 1
F2 F 0.2333(3) 0.7964(8) 0.3739(8) 0.188(5) Uani 0.835(14) 1 d D U . A 1
F3 F 0.1532(7) 0.8081(8) 0.4227(6) 0.181(4) Uani 0.835(14) 1 d D U . A 1
F4 F 0.3052(5) 0.3938(10) 0.3567(12) 0.193(6) Uani 0.696(18) 1 d D U . B 1
F5 F 0.2284(6) 0.2516(15) 0.2940(9) 0.209(7) Uani 0.696(18) 1 d D U . B 1
F6 F 0.2578(8) 0.2800(17) 0.4206(9) 0.211(7) Uani 0.696(18) 1 d D U . B 1
F7 F -0.0288(7) -0.0394(5) 0.3651(5) 0.128(4) Uani 0.793(17) 1 d D U . C 1
F8 F 0.0567(5) 0.0786(8) 0.4462(5) 0.157(4) Uani 0.793(17) 1 d D U . C 1
F9 F -0.0530(6) 0.1277(7) 0.4131(6) 0.157(4) Uani 0.793(17) 1 d D U . C 1
F1' F 0.1080(10) 0.850(2) 0.355(2) 0.105(11) Uani 0.165(14) 1 d D U . A 2
F2' F 0.191(2) 0.833(3) 0.310(2) 0.162(17) Uani 0.165(14) 1 d D U . A 2
F3' F 0.2138(17) 0.788(3) 0.4328(11) 0.125(13) Uani 0.165(14) 1 d D U . A 2
F4' F 0.266(2) 0.340(3) 0.2920(16) 0.217(15) Uani 0.304(18) 1 d D U . B 2
F5' F 0.2279(11) 0.2208(13) 0.361(2) 0.171(12) Uani 0.304(18) 1 d D U . B 2
F6' F 0.2992(12) 0.374(2) 0.4190(15) 0.177(12) Uani 0.304(18) 1 d D U . B 2
F7' F 0.0184(16) -0.0350(14) 0.3837(18) 0.102(10) Uani 0.207(17) 1 d D U . C 2
F8' F 0.0160(18) 0.123(2) 0.4551(9) 0.116(10) Uani 0.207(17) 1 d D U . C 2
F9' F -0.0812(6) 0.064(3) 0.3576(18) 0.158(15) Uani 0.207(17) 1 d D U . C 2
N1 N 0.0402(3) 0.5240(4) 0.1458(3) 0.0620(11) Uani 1 1 d . . . . .
N2 N 0.0963(2) 0.5395(5) 0.0647(3) 0.0678(13) Uani 1 1 d . . . . .
O1 O 0.07609(19) 0.6199(3) 0.3120(2) 0.0652(9) Uani 1 1 d . . . . .
O2 O 0.1208(2) 0.3775(4) 0.3104(3) 0.0800(11) Uani 1 1 d . . . . .
O3 O -0.0026(2) 0.2720(3) 0.3270(2) 0.0728(10) 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 C2 1.511(10) . ?
C1 F1 1.308(7) . ?
C1 F2 1.333(7) . ?
C1 F3 1.317(7) . ?
C1 F1' 1.343(10) . ?
C1 F2' 1.335(10) . ?
C1 F3' 1.332(10) . ?
C2 C3 1.368(10) . ?
C2 O1 1.250(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.349(10) . ?
C4 C5 1.521(10) . ?
C4 O2 1.257(9) . ?
C5 F4 1.334(8) . ?
C5 F5 1.329(9) . ?
C5 F6 1.321(8) . ?
C5 F4' 1.317(9) . ?
C5 F5' 1.323(9) . ?
C5 F6' 1.330(9) . ?
C6 C7 1.511(8) . ?
C6 F7 1.328(7) . ?
C6 F8 1.356(8) . ?
C6 F9 1.324(7) . ?
C6 F7' 1.335(9) . ?
C6 F8' 1.287(9) . ?
C6 F9' 1.346(9) . ?
C7 C8 1.377(7) . ?
C7 O3 1.238(6) . ?
C8 C7 1.377(7) 2 ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C9 N1 1.305(8) . ?
C9 N2 1.329(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.340(8) . ?
C10 N1 1.383(6) . ?
C11 H11 0.9300 . ?
C11 N2 1.344(8) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C12 N2 1.463(9) . ?
Dy1 N1 2.467(4) 2 ?
Dy1 N1 2.467(4) . ?
Dy1 O1 2.358(4) . ?
Dy1 O1 2.358(4) 2 ?
Dy1 O2 2.346(4) 2 ?
Dy1 O2 2.346(4) . ?
Dy1 O3 2.347(3) . ?
Dy1 O3 2.347(3) 2 ?

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
F1 C1 C2 112.3(6) . . ?
F1 C1 F2 106.9(7) . . ?
F1 C1 F3 108.4(8) . . ?
F2 C1 C2 111.4(7) . . ?
F3 C1 C2 110.7(7) . . ?
F3 C1 F2 106.9(6) . . ?
F1' C1 C2 114.4(12) . . ?
F2' C1 C2 113.9(17) . . ?
F2' C1 F1' 105.2(10) . . ?
F3' C1 C2 111.5(15) . . ?
F3' C1 F1' 105.3(10) . . ?
F3' C1 F2' 105.8(10) . . ?
C3 C2 C1 119.3(6) . . ?
O1 C2 C1 113.6(6) . . ?
O1 C2 C3 127.2(6) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.4(7) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5 119.4(8) . . ?
O2 C4 C3 128.0(7) . . ?
O2 C4 C5 112.5(8) . . ?
F4 C5 C4 112.8(8) . . ?
F5 C5 C4 112.1(8) . . ?
F5 C5 F4 106.3(8) . . ?
F6 C5 C4 110.0(8) . . ?
F6 C5 F4 107.6(8) . . ?
F6 C5 F5 107.7(8) . . ?
F4' C5 C4 110.0(14) . . ?
F4' C5 F5' 107.8(10) . . ?
F4' C5 F6' 108.2(10) . . ?
F5' C5 C4 114.6(12) . . ?
F5' C5 F6' 107.4(9) . . ?
F6' C5 C4 108.6(12) . . ?
F7 C6 C7 116.5(6) . . ?
F7 C6 F8 106.9(7) . . ?
F8 C6 C7 109.1(7) . . ?
F9 C6 C7 113.7(6) . . ?
F9 C6 F7 106.2(7) . . ?
F9 C6 F8 103.5(6) . . ?
F7' C6 C7 110.7(12) . . ?
F7' C6 F9' 106.1(9) . . ?
F8' C6 C7 119.9(11) . . ?
F8' C6 F7' 108.9(10) . . ?
F8' C6 F9' 107.7(9) . . ?
F9' C6 C7 102.5(13) . . ?
C8 C7 C6 117.9(5) . . ?
O3 C7 C6 113.7(5) . . ?
O3 C7 C8 128.4(6) . . ?
C7 C8 C7 122.3(8) 2 . ?
C7 C8 H8 118.9 2 . ?
C7 C8 H8 118.9 . . ?
N1 C9 H9 124.0 . . ?
N1 C9 N2 112.1(5) . . ?
N2 C9 H9 124.0 . . ?
C11 C10 H10 125.3 . . ?
C11 C10 N1 109.3(6) . . ?
N1 C10 H10 125.3 . . ?
C10 C11 H11 126.6 . . ?
C10 C11 N2 106.7(5) . . ?
N2 C11 H11 126.6 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
N1 Dy1 N1 141.7(2) 2 . ?
O1 Dy1 N1 74.51(14) . 2 ?
O1 Dy1 N1 75.96(14) 2 2 ?
O1 Dy1 N1 74.51(14) 2 . ?
O1 Dy1 N1 75.96(14) . . ?
O1 Dy1 O1 78.12(18) 2 . ?
O2 Dy1 N1 110.32(15) 2 . ?
O2 Dy1 N1 82.12(15) . . ?
O2 Dy1 N1 110.31(15) . 2 ?
O2 Dy1 N1 82.12(15) 2 2 ?
O2 Dy1 O1 71.17(14) 2 2 ?
O2 Dy1 O1 145.06(15) . 2 ?
O2 Dy1 O1 71.17(14) . . ?
O2 Dy1 O1 145.06(15) 2 . ?
O2 Dy1 O2 142.7(2) . 2 ?
O2 Dy1 O3 75.70(15) 2 . ?
O2 Dy1 O3 74.69(15) 2 2 ?
O2 Dy1 O3 74.68(15) . . ?
O2 Dy1 O3 75.70(15) . 2 ?
O3 Dy1 N1 143.80(14) . . ?
O3 Dy1 N1 73.57(13) . 2 ?
O3 Dy1 N1 143.80(14) 2 2 ?
O3 Dy1 N1 73.57(13) 2 . ?
O3 Dy1 O1 120.30(13) 2 2 ?
O3 Dy1 O1 137.37(14) 2 . ?
O3 Dy1 O1 120.30(13) . . ?
O3 Dy1 O1 137.37(14) . 2 ?
O3 Dy1 O3 74.00(17) . 2 ?
C9 N1 C10 104.5(5) . . ?
C9 N1 Dy1 129.0(4) . . ?
C10 N1 Dy1 125.9(4) . . ?
C9 N2 C11 107.4(5) . . ?
C9 N2 C12 126.0(6) . . ?
C11 N2 C12 126.6(6) . . ?
C2 O1 Dy1 134.4(4) . . ?
C4 O2 Dy1 134.0(4) . . ?
C7 O3 Dy1 133.4(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
C1 C2 C3 C4 173.2(8) . . . . ?
C1 C2 O1 Dy1 169.0(4) . . . . ?
C2 C3 C4 C5 -174.8(7) . . . . ?
C2 C3 C4 O2 5.2(15) . . . . ?
C3 C2 O1 Dy1 -11.9(10) . . . . ?
C3 C4 C5 F4 -15.6(14) . . . . ?
C3 C4 C5 F5 -135.6(13) . . . . ?
C3 C4 C5 F6 104.6(14) . . . . ?
C3 C4 C5 F4' -76(2) . . . . ?
C3 C4 C5 F5' 162.0(19) . . . . ?
C3 C4 C5 F6' 42(2) . . . . ?
C3 C4 O2 Dy1 13.3(13) . . . . ?
C5 C4 O2 Dy1 -166.7(5) . . . . ?
C6 C7 C8 C7 178.8(7) . . . 2 ?
C6 C7 O3 Dy1 -177.1(4) . . . . ?
C8 C7 O3 Dy1 3.4(10) . . . . ?
C10 C11 N2 C9 0.7(7) . . . . ?
C10 C11 N2 C12 -178.9(6) . . . . ?
C11 C10 N1 C9 -0.3(6) . . . . ?
C11 C10 N1 Dy1 172.2(4) . . . . ?
F1 C1 C2 C3 127.6(9) . . . . ?
F1 C1 C2 O1 -53.2(9) . . . . ?
F2 C1 C2 C3 7.8(11) . . . . ?
F2 C1 C2 O1 -173.0(7) . . . . ?
F3 C1 C2 C3 -111.1(10) . . . . ?
F3 C1 C2 O1 68.2(9) . . . . ?
F7 C6 C7 C8 -17.3(11) . . . . ?
F7 C6 C7 O3 163.3(8) . . . . ?
F8 C6 C7 C8 103.8(8) . . . . ?
F8 C6 C7 O3 -75.7(8) . . . . ?
F9 C6 C7 C8 -141.3(7) . . . . ?
F9 C6 C7 O3 39.2(10) . . . . ?
F1' C1 C2 C3 -174(2) . . . . ?
F1' C1 C2 O1 6(2) . . . . ?
F2' C1 C2 C3 65(2) . . . . ?
F2' C1 C2 O1 -115(2) . . . . ?
F3' C1 C2 C3 -54(2) . . . . ?
F3' C1 C2 O1 125(2) . . . . ?
F7' C6 C7 C8 24.1(16) . . . . ?
F7' C6 C7 O3 -155.4(15) . . . . ?
F8' C6 C7 C8 152.2(18) . . . . ?
F8' C6 C7 O3 -27(2) . . . . ?
F9' C6 C7 C8 -88.7(17) . . . . ?
F9' C6 C7 O3 91.9(17) . . . . ?
N1 C9 N2 C11 -1.0(7) . . . . ?
N1 C9 N2 C12 178.7(6) . . . . ?
N1 C10 C11 N2 -0.3(7) . . . . ?
N2 C9 N1 C10 0.8(7) . . . . ?
N2 C9 N1 Dy1 -171.4(3) . . . . ?
O1 C2 C3 C4 -5.9(14) . . . . ?
O2 C4 C5 F4 164.4(11) . . . . ?
O2 C4 C5 F5 44.4(13) . . . . ?
O2 C4 C5 F6 -75.4(13) . . . . ?
O2 C4 C5 F4' 104(2) . . . . ?
O2 C4 C5 F5' -18(2) . . . . ?
O2 C4 C5 F6' -138(2) . . . . ?
O3 C7 C8 C7 -1.8(5) . . . 2 ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1515832'
_audit_update_record             
;
2016-11-09 deposited with the CCDC.
2016-12-21 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         'C23 H15 Ho F18 N4 O6'
_chemical_formula_sum            'C23 H15 F18 Ho N4 O6'
_chemical_formula_weight         950.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2180 4.6780 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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                   20.079(7)
_cell_length_b                   10.639(2)
_cell_length_c                   18.035(9)
_cell_angle_alpha                90
_cell_angle_beta                 113.89(3)
_cell_angle_gamma                90
_cell_volume                     3523(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    7587
_cell_measurement_theta_min      2.0476
_cell_measurement_theta_max      27.8904

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.792
_exptl_crystal_F_000             1832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    2.382
_shelx_estimated_absorpt_T_min   0.647
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_T_max  0.751
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14168
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.0705
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.212
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_full        25.010
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3113
_reflns_number_gt                2801
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXL-2014/7
_computing_publication_material  SHELXL-2014/7
_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)+(0.0698P)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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0163(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3111
_refine_ls_number_parameters     322
_refine_ls_number_restraints     232
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.115
_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
Ho1 Ho 0.5000 0.44736(2) 0.2500 0.0499(2) Uani 1 2 d S T P . .
F1 F 0.2730(16) 0.791(3) 0.0873(19) 0.160(7) Uani 0.319(18) 1 d . U P A 1
F2 F 0.3542(16) 0.845(3) 0.2084(14) 0.140(7) Uani 0.319(18) 1 d D U P A 1
F3 F 0.3779(14) 0.831(2) 0.110(2) 0.147(6) Uani 0.319(18) 1 d D U P A 1
F1' F 0.2685(6) 0.7994(12) 0.1363(11) 0.164(4) Uani 0.681(18) 1 d . U P A 2
F2' F 0.3811(7) 0.8544(10) 0.1937(8) 0.144(5) Uani 0.681(18) 1 d D U P A 2
F3' F 0.3382(9) 0.8004(11) 0.0707(7) 0.152(4) Uani 0.681(18) 1 d D U P A 2
F4 F 0.1929(7) 0.3955(18) 0.1044(17) 0.185(6) Uani 0.444(15) 1 d D U P B 3
F5 F 0.2628(13) 0.295(3) 0.2219(10) 0.196(7) Uani 0.444(15) 1 d D U P B 3
F6 F 0.2652(11) 0.2316(17) 0.1140(17) 0.181(6) Uani 0.444(15) 1 d D U P B 3
F4' F 0.2320(9) 0.303(2) 0.0702(8) 0.184(5) Uani 0.556(15) 1 d D U P B 4
F5' F 0.1997(8) 0.3826(16) 0.1606(14) 0.175(5) Uani 0.556(15) 1 d D U P B 4
F6' F 0.2716(10) 0.2327(15) 0.1926(13) 0.191(6) Uani 0.556(15) 1 d D U P B 4
F7 F 0.4569(10) 0.1329(9) 0.4224(9) 0.135(4) Uani 0.65(2) 1 d D U P C 5
F8 F 0.4638(10) -0.0353(9) 0.3630(8) 0.116(4) Uani 0.65(2) 1 d D U P C 5
F9 F 0.5597(7) 0.0764(14) 0.4435(7) 0.140(4) Uani 0.65(2) 1 d D U P C 5
F7' F 0.4234(10) 0.103(3) 0.3793(18) 0.146(6) Uani 0.35(2) 1 d D U P C 6
F8' F 0.5066(17) -0.0415(11) 0.3779(14) 0.106(5) Uani 0.35(2) 1 d D U P C 6
F9' F 0.5369(14) 0.102(3) 0.4584(8) 0.135(6) Uani 0.35(2) 1 d D U P C 6
C1 C 0.3359(4) 0.7742(8) 0.1420(5) 0.116(3) Uani 1 1 d D . . . .
C2 C 0.3576(3) 0.6403(6) 0.1641(3) 0.0739(16) Uani 1 1 d . . . . .
C3 C 0.3041(4) 0.5536(7) 0.1553(6) 0.096(3) Uani 1 1 d . . . . .
H3 H 0.2565 0.5810 0.1413 0.116 Uiso 1 1 calc R U . . .
C4 C 0.3191(4) 0.4293(8) 0.1667(5) 0.091(2) Uani 1 1 d . . . . .
C5 C 0.2561(5) 0.3366(11) 0.1484(6) 0.143(4) Uani 1 1 d D . . . .
C6 C 0.4916(5) 0.0792(6) 0.3835(5) 0.108(3) Uani 1 1 d D . . . .
C7 C 0.4967(4) 0.1569(5) 0.3156(3) 0.0753(16) Uani 1 1 d . . . . .
C8 C 0.5000 0.0951(8) 0.2500 0.090(3) Uani 1 2 d S T P . .
H8 H 0.5000 0.0077 0.2500 0.108 Uiso 1 2 calc R U P . .
C9 C 0.5754(4) 0.4626(5) 0.1103(4) 0.0645(15) Uani 1 1 d . . . . .
H9 H 0.5849 0.3767 0.1158 0.077 Uiso 1 1 calc R U . . .
C10 C 0.5388(3) 0.6474(5) 0.1212(4) 0.0705(14) Uani 1 1 d . . . . .
H10 H 0.5172 0.7140 0.1366 0.085 Uiso 1 1 calc R U . . .
C11 C 0.5732(3) 0.6563(7) 0.0724(4) 0.0779(16) Uani 1 1 d . . . . .
H11 H 0.5803 0.7290 0.0479 0.093 Uiso 1 1 calc R U . . .
C12 C 0.6378(4) 0.5014(10) 0.0176(4) 0.097(2) Uani 1 1 d . . . . .
H12A H 0.6877 0.5265 0.0459 0.145 Uiso 1 1 calc R U . . .
H12B H 0.6175 0.5416 -0.0345 0.145 Uiso 1 1 calc R U . . .
H12C H 0.6353 0.4119 0.0106 0.145 Uiso 1 1 calc R U . . .
N1 N 0.5400(2) 0.5238(4) 0.1461(3) 0.0579(10) Uani 1 1 d . . . . .
N2 N 0.5961(3) 0.5389(5) 0.0651(3) 0.0674(13) Uani 1 1 d . . . . .
O1 O 0.42444(18) 0.6190(3) 0.1882(2) 0.0633(9) Uani 1 1 d . . . . .
O2 O 0.3799(2) 0.3766(4) 0.1904(3) 0.0795(11) Uani 1 1 d . . . . .
O3 O 0.4979(2) 0.2725(3) 0.3271(2) 0.0689(9) 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
Ho1 O2 2.332(4) 2_655 ?
Ho1 O2 2.332(4) . ?
Ho1 O3 2.333(3) . ?
Ho1 O3 2.333(3) 2_655 ?
Ho1 O1 2.347(3) 2_655 ?
Ho1 O1 2.347(3) . ?
Ho1 N1 2.457(4) . ?
Ho1 N1 2.457(4) 2_655 ?
F1 C1 1.26(2) . ?
F2 C1 1.332(10) . ?
F3 C1 1.341(10) . ?
F1' C1 1.342(13) . ?
F2' C1 1.317(9) . ?
F3' C1 1.335(9) . ?
F4 C5 1.349(10) . ?
F5 C5 1.349(10) . ?
F6 C5 1.326(10) . ?
F4' C5 1.341(9) . ?
F5' C5 1.331(9) . ?
F6' C5 1.324(9) . ?
F7 C6 1.304(8) . ?
F8 C6 1.328(8) . ?
F9 C6 1.358(9) . ?
F7' C6 1.363(10) . ?
F8' C6 1.332(9) . ?
F9' C6 1.311(10) . ?
C1 C2 1.496(10) . ?
C2 O1 1.253(6) . ?
C2 C3 1.377(10) . ?
C3 C4 1.353(9) . ?
C3 H3 0.9300 . ?
C4 O2 1.252(10) . ?
C4 C5 1.530(11) . ?
C6 C7 1.515(9) . ?
C7 O3 1.247(6) . ?
C7 C8 1.377(7) . ?
C8 C7 1.377(7) 2_655 ?
C8 H8 0.9300 . ?
C9 N1 1.311(8) . ?
C9 N2 1.331(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.324(8) . ?
C10 N1 1.386(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.356(8) . ?
C11 H11 0.9300 . ?
C12 N2 1.473(9) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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 Ho1 O2 142.3(2) 2_655 . ?
O2 Ho1 O3 74.49(15) 2_655 . ?
O2 Ho1 O3 75.67(15) . . ?
O2 Ho1 O3 75.67(15) 2_655 2_655 ?
O2 Ho1 O3 74.49(15) . 2_655 ?
O3 Ho1 O3 74.26(16) . 2_655 ?
O2 Ho1 O1 71.54(14) 2_655 2_655 ?
O2 Ho1 O1 144.99(14) . 2_655 ?
O3 Ho1 O1 120.08(13) . 2_655 ?
O3 Ho1 O1 137.66(13) 2_655 2_655 ?
O2 Ho1 O1 144.99(14) 2_655 . ?
O2 Ho1 O1 71.54(14) . . ?
O3 Ho1 O1 137.66(13) . . ?
O3 Ho1 O1 120.08(13) 2_655 . ?
O1 Ho1 O1 77.86(18) 2_655 . ?
O2 Ho1 N1 82.08(15) 2_655 . ?
O2 Ho1 N1 110.58(15) . . ?
O3 Ho1 N1 143.98(14) . . ?
O3 Ho1 N1 73.67(13) 2_655 . ?
O1 Ho1 N1 75.93(14) 2_655 . ?
O1 Ho1 N1 74.23(14) . . ?
O2 Ho1 N1 110.58(15) 2_655 2_655 ?
O2 Ho1 N1 82.08(15) . 2_655 ?
O3 Ho1 N1 73.67(13) . 2_655 ?
O3 Ho1 N1 143.98(14) 2_655 2_655 ?
O1 Ho1 N1 74.23(14) 2_655 2_655 ?
O1 Ho1 N1 75.93(14) . 2_655 ?
N1 Ho1 N1 141.4(2) . 2_655 ?
F1 C1 F2 116.6(19) . . ?
F2' C1 F3' 105.4(11) . . ?
F1 C1 F3 101.8(18) . . ?
F2 C1 F3 98.1(19) . . ?
F2' C1 F1' 108.0(10) . . ?
F3' C1 F1' 108.1(9) . . ?
F1 C1 C2 115.8(15) . . ?
F2' C1 C2 112.7(8) . . ?
F2 C1 C2 110.6(17) . . ?
F3' C1 C2 109.6(8) . . ?
F3 C1 C2 112.2(11) . . ?
F1' C1 C2 112.7(9) . . ?
O1 C2 C3 126.5(6) . . ?
O1 C2 C1 114.9(6) . . ?
C3 C2 C1 118.6(6) . . ?
C4 C3 C2 121.5(7) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
O2 C4 C3 128.1(7) . . ?
O2 C4 C5 113.0(8) . . ?
C3 C4 C5 118.9(8) . . ?
F6' C5 F5' 102.4(15) . . ?
F6' C5 F4' 108.0(14) . . ?
F5' C5 F4' 107.6(13) . . ?
F6 C5 F5 102.0(18) . . ?
F6 C5 F4 113.0(16) . . ?
F5 C5 F4 115.1(17) . . ?
F6' C5 C4 115.9(10) . . ?
F6 C5 C4 112.7(10) . . ?
F5' C5 C4 114.3(10) . . ?
F4' C5 C4 108.2(9) . . ?
F5 C5 C4 104.6(11) . . ?
F4 C5 C4 109.0(11) . . ?
F7 C6 F8 107.2(10) . . ?
F9' C6 F8' 100.1(16) . . ?
F7 C6 F9 99.5(9) . . ?
F8 C6 F9 112.0(11) . . ?
F9' C6 F7' 106.5(14) . . ?
F8' C6 F7' 115.2(16) . . ?
F7 C6 C7 115.0(7) . . ?
F9' C6 C7 119.0(12) . . ?
F8 C6 C7 115.8(8) . . ?
F8' C6 C7 111.9(11) . . ?
F9 C6 C7 106.2(8) . . ?
F7' C6 C7 104.5(11) . . ?
O3 C7 C8 127.6(5) . . ?
O3 C7 C6 114.0(5) . . ?
C8 C7 C6 118.5(5) . . ?
C7 C8 C7 123.0(8) . 2_655 ?
C7 C8 H8 118.5 . . ?
C7 C8 H8 118.5 2_655 . ?
N1 C9 N2 111.4(5) . . ?
N1 C9 H9 124.3 . . ?
N2 C9 H9 124.3 . . ?
C11 C10 N1 109.8(6) . . ?
C11 C10 H10 125.1 . . ?
N1 C10 H10 125.1 . . ?
C10 C11 N2 106.7(5) . . ?
C10 C11 H11 126.6 . . ?
N2 C11 H11 126.6 . . ?
N2 C12 H12A 109.5 . . ?
N2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 N1 C10 104.7(4) . . ?
C9 N1 Ho1 128.4(4) . . ?
C10 N1 Ho1 126.3(4) . . ?
C9 N2 C11 107.4(5) . . ?
C9 N2 C12 125.6(6) . . ?
C11 N2 C12 127.0(6) . . ?
C2 O1 Ho1 134.5(4) . . ?
C4 O2 Ho1 134.2(5) . . ?
C7 O3 Ho1 133.7(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
F1 C1 C2 O1 150(2) . . . . ?
F2' C1 C2 O1 -41.9(13) . . . . ?
F2 C1 C2 O1 -74.8(17) . . . . ?
F3' C1 C2 O1 75.1(11) . . . . ?
F3 C1 C2 O1 33.6(19) . . . . ?
F1' C1 C2 O1 -164.4(10) . . . . ?
F1 C1 C2 C3 -29(2) . . . . ?
F2' C1 C2 C3 139.2(12) . . . . ?
F2 C1 C2 C3 106.3(17) . . . . ?
F3' C1 C2 C3 -103.8(12) . . . . ?
F3 C1 C2 C3 -145.3(18) . . . . ?
F1' C1 C2 C3 16.7(13) . . . . ?
O1 C2 C3 C4 -5.3(14) . . . . ?
C1 C2 C3 C4 173.5(8) . . . . ?
C2 C3 C4 O2 4.7(16) . . . . ?
C2 C3 C4 C5 -174.4(8) . . . . ?
O2 C4 C5 F6' 31.1(18) . . . . ?
C3 C4 C5 F6' -149.7(16) . . . . ?
O2 C4 C5 F6 -38.0(18) . . . . ?
C3 C4 C5 F6 141.3(17) . . . . ?
O2 C4 C5 F5' 149.9(14) . . . . ?
C3 C4 C5 F5' -30.8(18) . . . . ?
O2 C4 C5 F4' -90.3(14) . . . . ?
C3 C4 C5 F4' 89.0(15) . . . . ?
O2 C4 C5 F5 72.0(17) . . . . ?
C3 C4 C5 F5 -108.7(17) . . . . ?
O2 C4 C5 F4 -164.3(16) . . . . ?
C3 C4 C5 F4 15(2) . . . . ?
F7 C6 C7 O3 30.2(13) . . . . ?
F9' C6 C7 O3 -50.1(18) . . . . ?
F8 C6 C7 O3 156.1(12) . . . . ?
F8' C6 C7 O3 -166.1(16) . . . . ?
F9 C6 C7 O3 -78.8(10) . . . . ?
F7' C6 C7 O3 68.5(16) . . . . ?
F7 C6 C7 C8 -150.2(10) . . . . ?
F9' C6 C7 C8 129.5(17) . . . . ?
F8 C6 C7 C8 -24.3(14) . . . . ?
F8' C6 C7 C8 13.5(18) . . . . ?
F9 C6 C7 C8 100.8(9) . . . . ?
F7' C6 C7 C8 -111.9(16) . . . . ?
O3 C7 C8 C7 -1.8(5) . . . 2_655 ?
C6 C7 C8 C7 178.6(7) . . . 2_655 ?
N1 C10 C11 N2 0.5(7) . . . . ?
N2 C9 N1 C10 -0.1(7) . . . . ?
N2 C9 N1 Ho1 -171.8(4) . . . . ?
C11 C10 N1 C9 -0.2(7) . . . . ?
C11 C10 N1 Ho1 171.7(4) . . . . ?
N1 C9 N2 C11 0.4(7) . . . . ?
N1 C9 N2 C12 179.1(6) . . . . ?
C10 C11 N2 C9 -0.5(7) . . . . ?
C10 C11 N2 C12 -179.2(6) . . . . ?
C3 C2 O1 Ho1 -12.1(10) . . . . ?
C1 C2 O1 Ho1 169.1(5) . . . . ?
C3 C4 O2 Ho1 13.3(14) . . . . ?
C5 C4 O2 Ho1 -167.5(5) . . . . ?
C8 C7 O3 Ho1 3.6(10) . . . . ?
C6 C7 O3 Ho1 -176.9(5) . . . . ?

_refine_diff_density_max         2.012
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.109

