# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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 
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data_1-la_sq
_database_code_depnum_ccdc_archive 'CCDC 1569937'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F8 La O8 [+ C H4 O]'
_chemical_formula_sum            'C26 H20 F8 La O8 [+ C H4 O]'
_chemical_formula_weight         783.37
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
La La -0.2871 2.4523 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.082(5)
_cell_length_b                   11.486(5)
_cell_length_c                   15.194(5)
_cell_angle_alpha                103.281(5)
_cell_angle_beta                 96.017(5)
_cell_angle_gamma                114.500(5)
_cell_volume                     1518.0(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5297
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5273
_cell_measurement_theta_min      3.5145
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.500
_exptl_absorpt_correction_T_max  0.741
_exptl_absorpt_correction_T_min  0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.644
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             738
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10225
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.521
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Oxford Xcalibur Gemini Ultra diffractometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4875
_reflns_number_total             5309
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
 From the SQUEEZE data output we see that the contribution of some 40 electrons were removed the unit cell by the SQUEEZE process.  With methanol having 18 electrons, this 40-electron value could be in accord with the contribution of some 2.2 MeOH molecules being removed from the unit cell (or 1.1 MeOH molecules per asymmetric unit). This being the case the suggested formulation with one CH₃OH is consistent with the value deduced from the squeeze data.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         4.725
_refine_diff_density_min         -3.532
_refine_diff_density_rms         0.269
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.184
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5309
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1151
_refine_ls_R_factor_gt           0.1095
_refine_ls_restrained_S_all      1.177
_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)+(0.0495P)²+74.5942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2869
_refine_ls_wR_factor_ref         0.2904
_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, All O(H) groups
2. Restrained distances
 O8-H8A
 0.85 with sigma of 0.01
 O7-H7A
 0.85 with sigma of 0.01
 C26-H8A
 1.909906 with sigma of 0.02
 La1-H8A
 3.062265 with sigma of 0.02
 C25-H7A
 1.845717 with sigma of 0.02
 La1-H7A
 3.171144 with sigma of 0.02
3. Rigid bond restraints
 C14, C13, C12, O3, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C14 \\sim C13 \\sim C12 \\sim O3 \\sim O4: within 3.8A with sigma of 0.04 and
sigma for terminal atoms of 0.08
Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.304(2) 0.902(2) 0.7715(15) 0.053(5) Uani 1 1 d . . . . .
C2 C 1.1456(19) 0.7857(17) 0.7422(12) 0.039(4) Uani 1 1 d . . . . .
C3 C 1.046(2) 0.7973(17) 0.7941(13) 0.044(4) Uani 1 1 d . . . . .
H3 H 1.079768 0.875015 0.843639 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8955(19) 0.6985(17) 0.7774(11) 0.037(4) Uani 1 1 d . . . . .
C5 C 0.798(2) 0.7257(19) 0.8371(12) 0.042(4) Uani 1 1 d . . . . .
C6 C 0.853(3) 0.810(2) 0.9274(14) 0.063(6) Uani 1 1 d . . . . .
H6 H 0.956343 0.857069 0.951203 0.075 Uiso 1 1 calc R . . . .
C7 C 0.756(3) 0.827(3) 0.984(2) 0.089(9) Uani 1 1 d . . . . .
H7 H 0.794461 0.884679 1.044043 0.107 Uiso 1 1 calc R . . . .
C8 C 0.608(3) 0.757(3) 0.9495(19) 0.083(8) Uani 1 1 d . . . . .
H8 H 0.542809 0.765426 0.986847 0.100 Uiso 1 1 calc R . . . .
C9 C 0.551(3) 0.674(3) 0.860(2) 0.095(10) Uani 1 1 d . . . . .
H9 H 0.447755 0.628054 0.837172 0.114 Uiso 1 1 calc R . . . .
C10 C 0.641(3) 0.657(3) 0.8040(17) 0.071(7) Uani 1 1 d . . . . .
H10 H 0.599344 0.599270 0.743544 0.085 Uiso 1 1 calc R . . . .
C11 C 0.905(3) 0.089(2) 0.7511(17) 0.071(7) Uani 1 1 d . . . . .
C12 C 0.955(2) 0.2333(18) 0.7590(13) 0.042(4) Uani 1 1 d . U . . .
C13 C 1.046(2) 0.327(2) 0.8439(14) 0.054(4) Uani 1 1 d . U . . .
H13 H 1.077092 0.296941 0.889963 0.065 Uiso 1 1 calc R . . . .
C14 C 1.0919(19) 0.4653(19) 0.8617(13) 0.044(4) Uani 1 1 d . U . . .
C15 C 1.1790(19) 0.5607(18) 0.9542(11) 0.036(4) Uani 1 1 d . . . . .
C16 C 1.219(3) 0.524(3) 1.0285(15) 0.076(7) Uani 1 1 d . . . . .
H16 H 1.194002 0.434016 1.019046 0.091 Uiso 1 1 calc R . . . .
C17 C 1.292(4) 0.611(3) 1.1166(17) 0.109(12) Uani 1 1 d . . . . .
H17 H 1.318129 0.581853 1.164587 0.131 Uiso 1 1 calc R . . . .
C18 C 1.326(3) 0.746(3) 1.1306(15) 0.071(7) Uani 1 1 d . . . . .
H18 H 1.375238 0.808005 1.189154 0.086 Uiso 1 1 calc R . . . .
C19 C 1.287(3) 0.790(2) 1.0576(15) 0.065(6) Uani 1 1 d . . . . .
H19 H 1.313769 0.880194 1.067380 0.078 Uiso 1 1 calc R . . . .
C20 C 1.209(3) 0.700(2) 0.9722(14) 0.061(6) Uani 1 1 d . . . . .
H20 H 1.175799 0.727845 0.925590 0.074 Uiso 1 1 calc R . . . .
C21 C 0.7743(19) 0.5259(18) 0.4439(12) 0.039(4) Uani 1 1 d . . . . .
C22 C 0.6324(19) 0.5128(19) 0.4738(11) 0.039(4) Uani 1 1 d . . . . .
C23 C 0.6242(19) 0.623(2) 0.5306(13) 0.046(5) Uani 1 1 d . . . . .
C24 C 0.493(2) 0.6127(19) 0.5562(13) 0.046(5) Uani 1 1 d . . . . .
C25 C 0.571(3) 0.176(2) 0.574(2) 0.086(9) Uani 1 1 d D . . . .
H25A H 0.468293 0.153209 0.575976 0.129 Uiso 1 1 calc R . . . .
H25B H 0.577873 0.151887 0.510211 0.129 Uiso 1 1 calc R . . . .
H25C H 0.604871 0.127843 0.606551 0.129 Uiso 1 1 calc R . . . .
C26 C 0.901(3) 0.129(2) 0.480(2) 0.082(8) Uani 1 1 d D . . . .
H26A H 0.855952 0.070088 0.418078 0.123 Uiso 1 1 calc R . . . .
H26B H 1.007446 0.159959 0.491894 0.123 Uiso 1 1 calc R . . . .
H26C H 0.861024 0.082135 0.523394 0.123 Uiso 1 1 calc R . . . .
O1 O 0.8375(13) 0.5876(12) 0.7130(9) 0.046(3) Uani 1 1 d . . . . .
O2 O 1.1083(18) 0.6851(12) 0.6742(7) 0.056(4) Uani 1 1 d . . . . .
O3 O 1.0680(10) 0.5266(10) 0.7929(7) 0.028(2) Uani 1 1 d . U . . .
O4 O 0.9093(16) 0.2546(13) 0.6884(9) 0.051(3) Uani 1 1 d . U . . .
O5 O 0.8661(14) 0.4993(14) 0.4895(8) 0.044(3) Uani 1 1 d . . . . .
O6 O 0.7992(14) 0.5634(14) 0.3717(8) 0.045(3) Uani 1 1 d . . . . .
O7 O 0.6579(14) 0.3120(14) 0.6145(11) 0.056(4) Uani 1 1 d D . . . .
H7A H 0.604(5) 0.346(5) 0.637(14) 0.085 Uiso 1 1 d DR . . . .
O8 O 0.8693(17) 0.2450(13) 0.4920(9) 0.055(4) Uani 1 1 d D . . . .
H8A H 0.852(16) 0.253(6) 0.4380(11) 0.082 Uiso 1 1 d DR . . . .
La1 La 0.94663(10) 0.44628(9) 0.63379(6) 0.0271(3) Uani 1 1 d D . . . .
F1 F 0.754(2) 0.0163(17) 0.7249(17) 0.138(9) Uani 1 1 d . . . . .
F2 F 0.957(2) 0.0314(17) 0.6874(15) 0.125(7) Uani 1 1 d . . . . .
F3 F 0.941(3) 0.0606(17) 0.8254(13) 0.145(9) Uani 1 1 d . . . . .
F4 F 0.7478(15) 0.7370(13) 0.5619(11) 0.083(5) Uani 1 1 d . . . . .
F5 F 0.4911(14) 0.7150(13) 0.6114(10) 0.073(4) Uani 1 1 d . . . . .
F6 F 1.321(2) 1.0084(18) 0.8296(16) 0.150(10) Uani 1 1 d . . . . .
F7 F 1.3579(19) 0.9339(19) 0.7042(12) 0.132(8) Uani 1 1 d . . . . .
F8 F 1.397(2) 0.866(2) 0.810(2) 0.166(11) 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 1.53(2) . ?
C1 F6 1.27(2) . ?
C1 F7 1.27(3) . ?
C1 F8 1.30(3) . ?
C2 C3 1.37(2) . ?
C2 O2 1.25(2) . ?
C3 C4 1.42(2) . ?
C4 C5 1.48(2) . ?
C4 O1 1.27(2) . ?
C5 C6 1.38(3) . ?
C5 C10 1.42(3) . ?
C6 C7 1.41(3) . ?
C7 C8 1.34(4) . ?
C8 C9 1.37(4) . ?
C9 C10 1.35(3) . ?
C11 C12 1.49(3) . ?
C11 F1 1.36(3) . ?
C11 F2 1.32(3) . ?
C11 F3 1.30(3) . ?
C12 C13 1.40(3) . ?
C12 O4 1.24(2) . ?
C13 C14 1.41(3) . ?
C14 C15 1.48(2) . ?
C14 O3 1.44(2) . ?
C15 C16 1.37(3) . ?
C15 C20 1.45(3) . ?
C16 C17 1.38(3) . ?
C17 C18 1.40(4) . ?
C18 C19 1.40(3) . ?
C19 C20 1.37(3) . ?
C21 C22 1.50(2) . ?
C21 O5 1.28(2) . ?
C21 O6 1.28(2) . ?
C21 La1 3.088(17) 2_766 ?
C22 C23 1.40(2) . ?
C22 C24 1.40(3) 2_666 ?
C23 C24 1.38(2) . ?
C23 F4 1.31(2) . ?
C24 F5 1.29(2) . ?
C25 O7 1.38(2) . ?
C26 O8 1.47(3) . ?
O1 La1 2.480(11) . ?
O2 La1 2.422(13) . ?
O3 La1 2.369(10) . ?
O4 La1 2.428(13) . ?
O5 La1 2.546(11) . ?
O5 La1 2.787(11) 2_766 ?
O6 La1 2.620(11) 2_766 ?
O7 La1 2.614(12) . ?
O8 La1 2.542(13) . ?

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
F6 C1 C2 115.6(18) . . ?
F6 C1 F8 106(2) . . ?
F7 C1 C2 113.7(17) . . ?
F7 C1 F6 107(2) . . ?
F7 C1 F8 103(2) . . ?
F8 C1 C2 110.2(19) . . ?
C3 C2 C1 116.9(16) . . ?
O2 C2 C1 121.7(17) . . ?
O2 C2 C3 121.4(17) . . ?
C2 C3 C4 124.3(16) . . ?
C3 C4 C5 118.9(15) . . ?
O1 C4 C3 123.8(15) . . ?
O1 C4 C5 117.3(16) . . ?
C6 C5 C4 122.8(18) . . ?
C6 C5 C10 117.5(18) . . ?
C10 C5 C4 119.6(17) . . ?
C5 C6 C7 121(2) . . ?
C8 C7 C6 119(2) . . ?
C7 C8 C9 121(2) . . ?
C10 C9 C8 122(3) . . ?
C9 C10 C5 120(2) . . ?
F1 C11 C12 112(2) . . ?
F2 C11 C12 112(2) . . ?
F2 C11 F1 106(2) . . ?
F3 C11 C12 117(2) . . ?
F3 C11 F1 104(3) . . ?
F3 C11 F2 105(2) . . ?
C13 C12 C11 117.0(17) . . ?
O4 C12 C11 114.8(17) . . ?
O4 C12 C13 128.2(18) . . ?
C12 C13 C14 122.2(18) . . ?
C13 C14 C15 120.8(18) . . ?
C13 C14 O3 124.4(16) . . ?
O3 C14 C15 114.7(15) . . ?
C16 C15 C14 124.3(19) . . ?
C16 C15 C20 116.6(18) . . ?
C20 C15 C14 118.7(16) . . ?
C15 C16 C17 125(3) . . ?
C16 C17 C18 117(2) . . ?
C17 C18 C19 121(2) . . ?
C20 C19 C18 120(2) . . ?
C19 C20 C15 120(2) . . ?
C22 C21 La1 175.0(12) . 2_766 ?
O5 C21 C22 120.4(16) . . ?
O5 C21 O6 121.4(15) . . ?
O5 C21 La1 64.5(8) . 2_766 ?
O6 C21 C22 118.2(15) . . ?
O6 C21 La1 57.0(8) . 2_766 ?
C23 C22 C21 121.4(17) . . ?
C24 C22 C21 118.8(15) 2_666 . ?
C24 C22 C23 119.8(16) 2_666 . ?
C24 C23 C22 121.7(17) . . ?
F4 C23 C22 117.4(16) . . ?
F4 C23 C24 120.9(17) . . ?
C23 C24 C22 118.5(16) . 2_666 ?
F5 C24 C22 121.3(16) . 2_666 ?
F5 C24 C23 120.0(17) . . ?
C4 O1 La1 132.1(11) . . ?
C2 O2 La1 136.6(13) . . ?
C14 O3 La1 135.0(9) . . ?
C12 O4 La1 137.9(13) . . ?
C21 O5 La1 148.6(10) . . ?
C21 O5 La1 91.1(10) . 2_766 ?
La1 O5 La1 119.9(4) . 2_766 ?
C21 O6 La1 98.9(10) . 2_766 ?
C25 O7 La1 126.9(12) . . ?
C26 O8 La1 129.8(14) . . ?
O1 La1 C21 140.2(5) . 2_766 ?
O1 La1 O5 127.7(4) . 2_766 ?
O1 La1 O5 84.9(4) . . ?
O1 La1 O6 142.4(4) . 2_766 ?
O1 La1 O7 67.6(4) . . ?
O1 La1 O8 138.5(5) . . ?
O2 La1 C21 74.2(5) . 2_766 ?
O2 La1 O1 66.1(5) . . ?
O2 La1 O4 140.8(4) . . ?
O2 La1 O5 69.5(4) . 2_766 ?
O2 La1 O5 78.4(4) . . ?
O2 La1 O6 81.9(5) . 2_766 ?
O2 La1 O7 131.1(5) . . ?
O2 La1 O8 135.4(4) . . ?
O3 La1 C21 96.6(4) . 2_766 ?
O3 La1 O1 73.9(4) . . ?
O3 La1 O2 71.2(4) . . ?
O3 La1 O4 71.7(4) . . ?
O3 La1 O5 148.0(4) . . ?
O3 La1 O5 115.8(4) . 2_766 ?
O3 La1 O6 77.5(3) . 2_766 ?
O3 La1 O7 109.9(4) . . ?
O3 La1 O8 140.0(4) . . ?
O4 La1 C21 98.2(5) . 2_766 ?
O4 La1 O1 114.2(4) . . ?
O4 La1 O5 140.1(5) . . ?
O4 La1 O5 117.5(4) . 2_766 ?
O4 La1 O6 78.3(4) . 2_766 ?
O4 La1 O7 74.1(5) . . ?
O4 La1 O8 72.5(4) . . ?
O5 La1 C21 24.4(4) 2_766 2_766 ?
O5 La1 C21 84.4(4) . 2_766 ?
O5 La1 O5 60.1(4) . 2_766 ?
O5 La1 O6 108.5(3) . 2_766 ?
O5 La1 O7 82.6(5) . . ?
O6 La1 C21 24.2(4) 2_766 2_766 ?
O6 La1 O5 48.6(3) 2_766 2_766 ?
O7 La1 C21 147.7(4) . 2_766 ?
O7 La1 O5 134.3(4) . 2_766 ?
O7 La1 O6 147.0(4) . 2_766 ?
O8 La1 C21 71.6(5) . 2_766 ?
O8 La1 O5 70.7(4) . . ?
O8 La1 O5 67.4(4) . 2_766 ?
O8 La1 O6 78.5(5) . 2_766 ?
O8 La1 O7 76.3(4) . . ?

_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_8-ho
_database_code_depnum_ccdc_archive 'CCDC 1569944'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 F8 Ho O7'
_chemical_formula_sum            'C25 H16 F8 Ho O7'
_chemical_formula_weight         745.31
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.053(5)
_cell_length_b                   10.465(5)
_cell_length_c                   13.841(5)
_cell_angle_alpha                90.024(5)
_cell_angle_beta                 102.266(5)
_cell_angle_gamma                109.466(5)
_cell_volume                     1337.5(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4484
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5250
_cell_measurement_theta_min      3.3085
_shelx_estimated_absorpt_T_max   0.625
_shelx_estimated_absorpt_T_min   0.482
_exptl_absorpt_coefficient_mu    3.056
_exptl_absorpt_correction_T_max  0.595
_exptl_absorpt_correction_T_min  0.451
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.851
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             722
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0398
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9162
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.996
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_min         3.315
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4253
_reflns_number_total             4689
_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       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         2.273
_refine_diff_density_min         -0.973
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         4689
_refine_ls_number_restraints     339
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+3.1511P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1379
_refine_ls_wR_factor_ref         0.1429
_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, All O(H) groups
2. Restrained distances
 C25-H5
 1.872785 with sigma of 0.02
 Ho1-H5
 2.879314 with sigma of 0.02
3. Rigid bond restraints
 C5A, C6A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15A, C16A, C17A, C18A, C19A, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F4, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim C10A: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim C20A: within 3.8A with
sigma of 0.04 and sigma for terminal atoms of 0.08
Uanis(C15A) \\sim Ueq, Uanis(C16A) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C20) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
5. Others
 Fixed Sof: C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5)
 H9(0.5) C10(0.5) H10(0.5) C5A(0.5) C6A(0.5) H6A(0.5) C7A(0.5) H7A(0.5)
 C8A(0.5) H8A(0.5) C9A(0.5) H9A(0.5) C10A(0.5) H10A(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) C18(0.5) C19(0.5) C20(0.5) H20(0.5) C15A(0.5) C16A(0.5)
 H16A(0.5) C17A(0.5) C18A(0.5) C19A(0.5) C20A(0.5) H20A(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6A(H6A), C7A(H7A),
 C8A(H8A), C9A(H9A), C10A(H10A), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C16A(H16A), C20A(H20A)
6.b Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C5A(C6A,C7A,C8A,C9A,C10A), C15(C16,C17,C18,C19,C20),
 C15A(C16A,C17A,C18A,C19A,C20A)
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C2 C 0.7832(13) 0.1696(11) 0.3144(8) 0.066(3) Uani 1 1 d . . . . .
C3 C 0.7498(13) 0.1658(10) 0.2147(7) 0.067(3) Uani 1 1 d . . . . .
H3 H 0.686426 0.085049 0.179660 0.081 Uiso 1 1 calc R . . . .
C4 C 0.8065(9) 0.2795(9) 0.1596(6) 0.0446(19) Uani 1 1 d . . . . .
C5 C 0.7745(16) 0.2537(12) 0.0484(7) 0.036(5) Uani 0.5 1 d . . P A 1
C6 C 0.8023(16) 0.3676(11) -0.0059(10) 0.047(5) Uani 0.5 1 d G . P A 1
H6 H 0.838328 0.454143 0.026502 0.057 Uiso 0.5 1 calc R . P A 1
C7 C 0.7761(18) 0.3522(14) -0.1087(10) 0.062(6) Uani 0.5 1 d G . P A 1
H7 H 0.794717 0.428378 -0.145068 0.074 Uiso 0.5 1 calc R . P A 1
C8 C 0.722(2) 0.2228(17) -0.1572(7) 0.065(7) Uani 0.5 1 d G . P A 1
H8 H 0.704764 0.212492 -0.225992 0.078 Uiso 0.5 1 calc R . P A 1
C9 C 0.6945(19) 0.1089(13) -0.1029(9) 0.082(7) Uani 0.5 1 d G . P A 1
H9 H 0.658422 0.022370 -0.135348 0.098 Uiso 0.5 1 calc R . P A 1
C10 C 0.7206(17) 0.1243(11) -0.0001(8) 0.056(5) Uani 0.5 1 d G . P A 1
H10 H 0.702032 0.048132 0.036221 0.068 Uiso 0.5 1 calc R . P A 1
C5A C 0.771(2) 0.278(2) 0.0492(10) 0.065(6) Uani 0.5 1 d . U P A 2
C6A C 0.8732(18) 0.362(2) 0.0023(15) 0.094(8) Uani 0.5 1 d G U P A 2
H6A H 0.960779 0.420097 0.039821 0.112 Uiso 0.5 1 calc R . P A 2
C7A C 0.845(2) 0.358(2) -0.1006(16) 0.096(8) Uani 0.5 1 d G U P A 2
H7A H 0.913227 0.414375 -0.131949 0.115 Uiso 0.5 1 calc R . P A 2
C8A C 0.714(2) 0.271(2) -0.1567(10) 0.082(7) Uani 0.5 1 d G U P A 2
H8A H 0.694840 0.268612 -0.225522 0.098 Uiso 0.5 1 calc R . P A 2
C9A C 0.6115(19) 0.187(2) -0.1098(11) 0.096(7) Uani 0.5 1 d G U P A 2
H9A H 0.524004 0.128569 -0.147326 0.115 Uiso 0.5 1 calc R . P A 2
C10A C 0.640(2) 0.190(2) -0.0069(11) 0.093(7) Uani 0.5 1 d G U P A 2
H10A H 0.571552 0.134288 0.024444 0.112 Uiso 0.5 1 calc R . P A 2
C11 C 0.772(2) 0.7459(18) 0.1047(10) 0.100(5) Uani 1 1 d . U . . .
C12 C 0.7441(13) 0.6369(11) 0.1806(7) 0.063(3) Uani 1 1 d . . . . .
C13 C 0.6108(13) 0.5415(14) 0.1743(8) 0.076(3) Uani 1 1 d . . . . .
H13 H 0.536206 0.541119 0.121243 0.091 Uiso 1 1 calc R . . . .
C14 C 0.5799(10) 0.4436(12) 0.2436(8) 0.065(3) Uani 1 1 d . . . . .
C15 C 0.4351(11) 0.3664(16) 0.2328(11) 0.048(4) Uani 0.5 1 d . U P B 1
C16 C 0.3228(14) 0.3829(18) 0.1617(12) 0.076(6) Uani 0.5 1 d G U P B 1
H16 H 0.343024 0.445765 0.114681 0.092 Uiso 0.5 1 calc R . P B 1
C17 C 0.1801(12) 0.305(2) 0.1609(15) 0.099(7) Uani 0.5 1 d G U P B 1
H17 H 0.104922 0.316477 0.113285 0.118 Uiso 1 1 calc R . . B 1
C18 C 0.1498(12) 0.212(2) 0.2311(17) 0.103(7) Uani 0.5 1 d G U P B 1
H18 H 0.054381 0.159695 0.230568 0.123 Uiso 1 1 calc R . . B 1
C19 C 0.2622(16) 0.1950(19) 0.3022(14) 0.102(7) Uani 0.5 1 d G U P B 1
H19 H 0.241944 0.132200 0.349248 0.123 Uiso 1 1 calc R . . B 1
C20 C 0.4049(14) 0.2725(16) 0.3031(12) 0.058(4) Uani 0.5 1 d G U P B 1
H20 H 0.480048 0.261488 0.350645 0.070 Uiso 0.5 1 calc R . P B 1
C15A C 0.436(2) 0.325(3) 0.247(2) 0.113(9) Uani 0.5 1 d . U P B 2
C16A C 0.308(3) 0.343(3) 0.197(2) 0.110(8) Uani 0.5 1 d G U P B 2
H16A H 0.312666 0.414371 0.156676 0.132 Uiso 0.5 1 calc R . P B 2
C17A C 0.175(2) 0.253(4) 0.206(3) 0.148(10) Uani 0.5 1 d G U P B 2
C18A C 0.169(2) 0.146(3) 0.267(3) 0.145(10) Uani 0.5 1 d G U P B 2
C19A C 0.296(3) 0.128(3) 0.317(2) 0.153(10) Uani 0.5 1 d G U P B 2
C20A C 0.429(3) 0.217(3) 0.307(2) 0.134(10) Uani 0.5 1 d G U P B 2
H20A H 0.514364 0.205626 0.340934 0.161 Uiso 0.5 1 calc R . P B 2
C21 C 0.7916(8) 0.4940(8) 0.5705(5) 0.0334(15) Uani 1 1 d . . . . .
C22 C 0.6424(7) 0.4972(8) 0.5339(5) 0.0327(15) Uani 1 1 d . . . . .
C23 C 0.6159(8) 0.5972(8) 0.4775(6) 0.0398(17) Uani 1 1 d . . . . .
C24 C 0.4774(9) 0.6012(9) 0.4436(6) 0.0420(18) Uani 1 1 d . . . . .
C25 C 1.130(5) 0.837(3) 0.374(2) 0.31(3) Uani 1 1 d D . . . .
H25A H 1.219796 0.827201 0.368793 0.460 Uiso 1 1 calc GR . . . .
H25B H 1.149168 0.919380 0.413374 0.460 Uiso 1 1 calc GR . . . .
H25C H 1.074781 0.840765 0.308870 0.460 Uiso 1 1 calc GR . . . .
C1 C 0.726(3) 0.0374(16) 0.3629(11) 0.135(9) Uani 1 1 d . . . . .
F1 F 0.834(2) 0.0109(10) 0.4220(9) 0.192(8) Uani 1 1 d . . . . .
F2 F 0.6547(17) -0.0657(10) 0.3022(8) 0.202(6) Uani 1 1 d . U . . .
F3 F 0.6514(19) 0.0522(16) 0.4226(13) 0.214(8) Uani 1 1 d . . . . .
F4 F 0.846(4) 0.8647(17) 0.1470(17) 0.36(2) Uani 1 1 d . U . . .
F5 F 0.871(2) 0.751(3) 0.0592(15) 0.237(10) Uani 1 1 d . . . . .
F6 F 0.6428(18) 0.7564(17) 0.0504(10) 0.205(7) Uani 1 1 d . . . . .
F7 F 0.7264(5) 0.6973(6) 0.4541(5) 0.0639(15) Uani 1 1 d . . . . .
F8 F 0.4630(6) 0.7052(6) 0.3915(5) 0.0730(18) Uani 1 1 d . . . . .
Ho1 Ho 0.92063(3) 0.50207(3) 0.35252(2) 0.03207(16) Uani 1 1 d D . . . .
O6 O 0.8736(5) 0.5118(6) 0.5108(3) 0.0354(11) Uani 1 1 d . . . . .
O2 O 0.8581(7) 0.6442(7) 0.2424(4) 0.0587(16) Uani 1 1 d . . . . .
O1 O 0.6765(6) 0.4283(8) 0.3133(4) 0.0574(17) Uani 1 1 d . . . . .
O3 O 0.8842(6) 0.3927(6) 0.2004(4) 0.0467(13) Uani 1 1 d . . . . .
O4 O 0.8612(7) 0.2719(6) 0.3769(4) 0.0527(15) Uani 1 1 d . . . . .
O5 O 1.0512(7) 0.7261(6) 0.4186(5) 0.0550(15) Uani 1 1 d . . . . .
O7 O 0.8338(6) 0.4758(6) 0.6590(4) 0.0450(13) Uiso 1 1 d . . . . .
H5 H 1.010(10) 0.762(4) 0.460(6) 0.068 Uiso 1 1 d DR . . . .


_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
C2 C3 1.347(14) . ?
C2 C1 1.525(17) . ?
C2 O4 1.288(12) . ?
C3 C4 1.434(13) . ?
C4 C5 1.509(12) . ?
C4 C5A 1.492(16) . ?
C4 O3 1.237(10) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C11 C12 1.548(18) . ?
C11 F4 1.28(2) . ?
C11 F5 1.27(2) . ?
C11 F6 1.398(19) . ?
C12 C13 1.363(17) . ?
C12 O2 1.256(11) . ?
C13 C14 1.409(17) . ?
C14 C15 1.385(14) . ?
C14 C15A 1.58(2) . ?
C14 O1 1.267(12) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C16A C17A 1.3900 . ?
C17A C18A 1.3900 . ?
C18A C19A 1.3900 . ?
C19A C20A 1.3900 . ?
C21 C22 1.489(10) . ?
C21 Ho1 2.849(7) 2_766 ?
C21 O6 1.258(9) . ?
C21 O7 1.245(9) . ?
C22 C23 1.369(11) . ?
C22 C24 1.393(11) 2_666 ?
C23 C24 1.387(11) . ?
C23 F7 1.347(9) . ?
C24 F8 1.336(9) . ?
C25 O5 1.40(3) . ?
C1 F1 1.32(3) . ?
C1 F2 1.270(16) . ?
C1 F3 1.27(3) . ?
Ho1 O6 2.346(5) . ?
Ho1 O6 2.533(5) 2_766 ?
Ho1 O2 2.269(6) . ?
Ho1 O1 2.255(6) . ?
Ho1 O3 2.295(5) . ?
Ho1 O4 2.324(6) . ?
Ho1 O5 2.344(6) . ?
Ho1 O7 2.441(6) 2_766 ?

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
C3 C2 C1 118.0(10) . . ?
O4 C2 C3 128.3(10) . . ?
O4 C2 C1 113.7(9) . . ?
C2 C3 C4 123.6(9) . . ?
C3 C4 C5 117.0(8) . . ?
C3 C4 C5A 124.5(11) . . ?
O3 C4 C3 122.3(8) . . ?
O3 C4 C5 120.6(9) . . ?
O3 C4 C5A 113.0(11) . . ?
C6 C5 C4 116.6(8) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 123.4(8) . . ?
C7 C6 C5 120.0 . . ?
C8 C7 C6 120.0 . . ?
C7 C8 C9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C5 120.0 . . ?
C6A C5A C4 118.9(13) . . ?
C6A C5A C10A 120.0 . . ?
C10A C5A C4 121.0(13) . . ?
C7A C6A C5A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
F4 C11 C12 112.0(15) . . ?
F4 C11 F6 105.2(18) . . ?
F5 C11 C12 116.5(13) . . ?
F5 C11 F4 91(2) . . ?
F5 C11 F6 118.3(15) . . ?
F6 C11 C12 111.2(16) . . ?
C13 C12 C11 122.0(11) . . ?
O2 C12 C11 111.9(12) . . ?
O2 C12 C13 126.0(10) . . ?
C12 C13 C14 123.6(9) . . ?
C13 C14 C15A 130.7(14) . . ?
C15 C14 C13 115.6(10) . . ?
O1 C14 C13 122.9(10) . . ?
O1 C14 C15 121.5(12) . . ?
O1 C14 C15A 106.0(14) . . ?
C14 C15 C16 124.6(10) . . ?
C14 C15 C20 115.3(10) . . ?
C16 C15 C20 120.0 . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C19 120.0 . . ?
C18 C19 C20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C16A C15A C14 115.6(18) . . ?
C16A C15A C20A 120.0 . . ?
C20A C15A C14 123.8(18) . . ?
C15A C16A C17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C18A C19A C20A 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C22 C21 Ho1 177.2(5) . 2_766 ?
O6 C21 C22 118.8(6) . . ?
O6 C21 Ho1 62.7(4) . 2_766 ?
O7 C21 C22 120.0(6) . . ?
O7 C21 Ho1 58.5(4) . 2_766 ?
O7 C21 O6 121.2(7) . . ?
C23 C22 C21 121.9(7) . . ?
C23 C22 C24 116.6(7) . 2_666 ?
C24 C22 C21 121.5(7) 2_666 . ?
C22 C23 C24 122.2(7) . . ?
F7 C23 C22 120.1(7) . . ?
F7 C23 C24 117.6(7) . . ?
C23 C24 C22 121.1(7) . 2_666 ?
F8 C24 C22 121.0(7) . 2_666 ?
F8 C24 C23 117.8(7) . . ?
F1 C1 C2 110.6(17) . . ?
F2 C1 C2 114.5(12) . . ?
F2 C1 F1 108(2) . . ?
F2 C1 F3 110(2) . . ?
F3 C1 C2 110.0(19) . . ?
F3 C1 F1 102.6(15) . . ?
O6 Ho1 C21 93.07(18) . 2_766 ?
O6 Ho1 C21 26.21(18) 2_766 2_766 ?
O6 Ho1 O6 67.37(18) . 2_766 ?
O6 Ho1 O7 118.17(17) . 2_766 ?
O2 Ho1 C21 125.2(2) . 2_766 ?
O2 Ho1 O6 142.1(2) . 2_766 ?
O2 Ho1 O6 118.0(2) . . ?
O2 Ho1 O3 75.8(2) . . ?
O2 Ho1 O4 140.7(2) . . ?
O2 Ho1 O5 71.9(2) . . ?
O2 Ho1 O7 104.2(2) . 2_766 ?
O1 Ho1 C21 160.1(3) . 2_766 ?
O1 Ho1 O6 79.75(19) . . ?
O1 Ho1 O6 139.6(2) . 2_766 ?
O1 Ho1 O2 74.0(3) . . ?
O1 Ho1 O3 81.6(2) . . ?
O1 Ho1 O4 77.6(3) . . ?
O1 Ho1 O5 120.0(3) . . ?
O1 Ho1 O7 158.6(2) . 2_766 ?
O3 Ho1 C21 97.6(2) . 2_766 ?
O3 Ho1 O6 152.2(2) . . ?
O3 Ho1 O6 118.02(19) . 2_766 ?
O3 Ho1 O4 73.7(2) . . ?
O3 Ho1 O5 132.6(2) . . ?
O3 Ho1 O7 77.3(2) . 2_766 ?
O4 Ho1 C21 83.1(2) . 2_766 ?
O4 Ho1 O6 75.48(19) . 2_766 ?
O4 Ho1 O6 82.3(2) . . ?
O4 Ho1 O5 147.2(2) . . ?
O4 Ho1 O7 92.6(2) . 2_766 ?
O5 Ho1 C21 75.0(2) . 2_766 ?
O5 Ho1 O6 75.0(2) . . ?
O5 Ho1 O6 74.1(2) . 2_766 ?
O5 Ho1 O7 78.2(2) . 2_766 ?
O7 Ho1 C21 25.77(19) 2_766 2_766 ?
O7 Ho1 O6 51.97(17) 2_766 2_766 ?
C21 O6 Ho1 91.1(4) . 2_766 ?
C21 O6 Ho1 153.6(5) . . ?
Ho1 O6 Ho1 112.63(18) . 2_766 ?
C12 O2 Ho1 134.0(7) . . ?
C14 O1 Ho1 135.8(7) . . ?
C4 O3 Ho1 134.7(6) . . ?
C2 O4 Ho1 128.4(6) . . ?
C25 O5 Ho1 129.6(14) . . ?
C21 O7 Ho1 95.8(4) . 2_766 ?

_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_5-eu_sq
_database_code_depnum_ccdc_archive 'CCDC 1569941'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 Eu F8 O8 [+ C H4 O]'
_chemical_formula_sum            'C26 H20 Eu F8 O8 [+ C H4 O]'
_chemical_formula_weight         764.38
_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 0.0033 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'
Eu Eu -0.1578 3.6682 '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'
O O 0.0106 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.066(5)
_cell_length_b                   11.407(5)
_cell_length_c                   15.017(5)
_cell_angle_alpha                103.584(5)
_cell_angle_beta                 95.519(5)
_cell_angle_gamma                114.501(5)
_cell_volume                     1488.2(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4801
_cell_measurement_temperature    293
_cell_measurement_theta_max      29.7995
_cell_measurement_theta_min      3.2376
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.202
_exptl_absorpt_correction_T_max  0.630
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             750
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9564
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.244
_diffrn_ambient_temperature      293
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4735
_reflns_number_total             5231
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
 From the SQUEEZE data output we see that the contribution of some 32 electrons were removed the unit cell by the SQUEEZE process.  With methanol having 18 electrons, this 31 electron value could be in accord with the contribution of some 1.7 MeOH molecules being removed from the unit cell (or ~0.9 MeOH molecules per asymmetric unit).
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         2.215
_refine_diff_density_min         -2.228
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5231
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0596P)²+0.2897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1157
_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, All O(H) groups
2. Restrained distances
 O7-H7
 0.85 with sigma of 0.01
 O8-H8
 0.85 with sigma of 0.01
 C25-H7
 1.885698 with sigma of 0.02
 Eu1-H7
 3.033179 with sigma of 0.02
 C26-H8
 1.895859 with sigma of 0.02
 Eu1-H8
 2.950832 with sigma of 0.02
3.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
3.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C13(H13), C3(H3), C6(H6),
 C10(H10), C9(H9), C7(H7A), C8(H8A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C16 C 1.2202(10) 0.5251(8) 1.0272(5) 0.065(2) Uani 1 1 d . . . . .
H16 H 1.200591 0.435397 1.017555 0.078 Uiso 1 1 calc R . . . .
C17 C 1.2937(10) 0.6208(9) 1.1154(5) 0.075(3) Uani 1 1 d . . . . .
H17 H 1.319848 0.593356 1.165160 0.090 Uiso 1 1 calc R . . . .
C18 C 1.3276(9) 0.7531(8) 1.1298(5) 0.061(2) Uani 1 1 d . . . . .
H18 H 1.379095 0.815761 1.188484 0.073 Uiso 1 1 calc R . . . .
C19 C 1.2863(9) 0.7939(8) 1.0584(5) 0.0577(19) Uani 1 1 d . . . . .
H19 H 1.308632 0.884204 1.067931 0.069 Uiso 1 1 calc R . . . .
C20 C 1.2104(7) 0.6992(7) 0.9710(4) 0.0459(15) Uani 1 1 d . . . . .
H20 H 1.181632 0.727465 0.922557 0.055 Uiso 1 1 calc R . . . .
C15 C 1.1768(6) 0.5660(6) 0.9540(4) 0.0379(13) Uani 1 1 d . . . . .
C14 C 1.0929(6) 0.4689(6) 0.8585(4) 0.0345(12) Uani 1 1 d . . . . .
C13 C 1.0451(8) 0.3298(6) 0.8414(4) 0.0470(16) Uani 1 1 d . . . . .
H13 H 1.073725 0.300080 0.889000 0.056 Uiso 1 1 calc R . . . .
C12 C 0.9583(7) 0.2359(6) 0.7577(4) 0.0392(14) Uani 1 1 d . . . . .
C11 C 0.9036(9) 0.0863(7) 0.7469(5) 0.0584(19) Uani 1 1 d . . . . .
C1 C 1.3019(7) 0.8958(7) 0.7656(4) 0.0469(16) Uani 1 1 d . . . . .
C2 C 1.1432(6) 0.7796(6) 0.7385(4) 0.0324(12) Uani 1 1 d . . . . .
C3 C 1.0436(7) 0.7938(5) 0.7912(4) 0.0354(13) Uani 1 1 d . . . . .
H3 H 1.076155 0.873984 0.839524 0.043 Uiso 1 1 calc R . . . .
C4 C 0.8946(7) 0.6939(6) 0.7764(4) 0.0339(12) Uani 1 1 d . . . . .
C5 C 0.7959(7) 0.7211(6) 0.8374(4) 0.0393(14) Uani 1 1 d . . . . .
C6 C 0.8556(9) 0.8100(7) 0.9292(5) 0.0537(17) Uani 1 1 d . . . . .
H6 H 0.958459 0.855966 0.952868 0.064 Uiso 1 1 calc R . . . .
C10 C 0.6443(8) 0.6543(8) 0.8044(5) 0.062(2) Uani 1 1 d . . . . .
H10 H 0.604406 0.594346 0.743866 0.074 Uiso 1 1 calc R . . . .
C9 C 0.5501(10) 0.6749(10) 0.8598(7) 0.082(3) Uani 1 1 d . . . . .
H9 H 0.447221 0.629896 0.836150 0.098 Uiso 1 1 calc R . . . .
C24 C 0.4939(6) 0.6088(6) 0.5572(4) 0.0348(13) Uani 1 1 d . . . . .
C23 C 0.6260(6) 0.6196(6) 0.5349(4) 0.0363(13) Uani 1 1 d . . . . .
C22 C 0.6353(6) 0.5114(5) 0.4769(3) 0.0283(11) Uani 1 1 d . . . . .
C21 C 0.7793(6) 0.5233(5) 0.4495(4) 0.0299(12) Uani 1 1 d . . . . .
C25 C 0.5777(8) 0.1729(7) 0.5753(6) 0.067(2) Uani 1 1 d D . . . .
H25A H 0.476506 0.153993 0.579121 0.100 Uiso 1 1 calc R . . . .
H25B H 0.582956 0.146446 0.510713 0.100 Uiso 1 1 calc R . . . .
H25C H 0.609436 0.123108 0.608325 0.100 Uiso 1 1 calc R . . . .
C26 C 0.9026(10) 0.1373(8) 0.4781(5) 0.061(2) Uani 1 1 d D . . . .
H26A H 0.855159 0.081179 0.414521 0.092 Uiso 1 1 calc R . . . .
H26B H 1.008509 0.166676 0.487442 0.092 Uiso 1 1 calc R . . . .
H26C H 0.863240 0.086715 0.520299 0.092 Uiso 1 1 calc R . . . .
O1 O 0.8390(4) 0.5795(4) 0.7137(3) 0.0385(9) Uani 1 1 d . . . . .
O2 O 1.1231(4) 0.6800(4) 0.6706(2) 0.0345(9) Uani 1 1 d . . . . .
O3 O 1.0653(5) 0.5175(4) 0.7960(3) 0.0383(9) Uani 1 1 d . . . . .
O4 O 0.9135(5) 0.2573(4) 0.6847(3) 0.0417(10) Uani 1 1 d . . . . .
O5 O 0.8634(4) 0.4969(4) 0.4994(2) 0.0344(9) Uani 1 1 d . . . . .
O6 O 0.8090(4) 0.5607(4) 0.3795(3) 0.0401(10) Uani 1 1 d . . . . .
O7 O 0.6728(5) 0.3139(4) 0.6167(3) 0.0525(11) Uani 1 1 d D . . . .
H7 H 0.621(3) 0.351(2) 0.641(5) 0.079 Uiso 1 1 d DR . . . .
O8 O 0.8740(5) 0.2531(4) 0.4962(3) 0.0387(9) Uani 1 1 d D . . . .
H8 H 0.854(7) 0.264(3) 0.4433(9) 0.058 Uiso 1 1 d DR . . . .
Eu1 Eu 0.94867(3) 0.44574(2) 0.63576(2) 0.02613(12) Uani 1 1 d D . . . .
F1 F 0.7579(6) 0.0172(5) 0.7184(5) 0.107(2) Uani 1 1 d . . . . .
F2 F 0.9589(8) 0.0319(5) 0.6835(4) 0.112(2) Uani 1 1 d . . . . .
F3 F 0.9393(8) 0.0609(5) 0.8246(4) 0.122(3) Uani 1 1 d . . . . .
F4 F 0.7498(4) 0.7382(4) 0.5704(3) 0.0732(14) Uani 1 1 d . . . . .
F5 F 0.4883(4) 0.7149(4) 0.6143(3) 0.0617(11) Uani 1 1 d . . . . .
F6 F 1.3161(7) 1.0069(5) 0.8201(5) 0.139(3) Uani 1 1 d . . . . .
F7 F 1.3557(6) 0.9209(6) 0.6940(3) 0.0989(19) Uani 1 1 d . . . . .
F8 F 1.3937(6) 0.8639(8) 0.8087(6) 0.147(3) Uani 1 1 d . . . . .
C7 C 0.7584(11) 0.8279(9) 0.9838(6) 0.075(2) Uani 1 1 d . . . . .
H7A H 0.796709 0.886106 1.044867 0.090 Uiso 1 1 calc R . . . .
C8 C 0.6070(11) 0.7613(10) 0.9495(6) 0.085(3) Uani 1 1 d . . . . .
H8A H 0.543050 0.774735 0.986926 0.102 Uiso 1 1 calc R . . . .


_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
C16 C17 1.400(10) . ?
C16 C15 1.389(9) . ?
C17 C18 1.359(11) . ?
C18 C19 1.360(10) . ?
C19 C20 1.389(9) . ?
C20 C15 1.365(9) . ?
C15 C14 1.498(8) . ?
C14 C13 1.402(8) . ?
C14 O3 1.259(7) . ?
C13 C12 1.367(9) . ?
C12 C11 1.522(9) . ?
C12 O4 1.258(7) . ?
C11 F1 1.311(9) . ?
C11 F2 1.309(9) . ?
C11 F3 1.318(8) . ?
C1 C2 1.530(8) . ?
C1 F6 1.279(8) . ?
C1 F7 1.288(7) . ?
C1 F8 1.296(9) . ?
C2 C3 1.373(8) . ?
C2 O2 1.264(6) . ?
C3 C4 1.413(8) . ?
C4 C5 1.490(8) . ?
C4 O1 1.272(7) . ?
C5 C6 1.403(9) . ?
C5 C10 1.367(10) . ?
C6 C7 1.382(10) . ?
C10 C9 1.375(11) . ?
C9 C8 1.369(12) . ?
C24 C23 1.366(8) . ?
C24 C22 1.377(7) 2_666 ?
C24 F5 1.334(6) . ?
C23 C22 1.377(7) . ?
C23 F4 1.343(6) . ?
C22 C21 1.506(7) . ?
C21 O5 1.252(6) . ?
C21 O6 1.240(7) . ?
C21 Eu1 3.057(5) 2_766 ?
C25 O7 1.425(8) . ?
C26 O8 1.437(8) . ?
O1 Eu1 2.392(4) . ?
O2 Eu1 2.402(4) . ?
O3 Eu1 2.361(4) . ?
O4 Eu1 2.335(4) . ?
O5 Eu1 2.430(4) . ?
O5 Eu1 2.909(4) 2_766 ?
O6 Eu1 2.501(4) 2_766 ?
O7 Eu1 2.497(5) . ?
O8 Eu1 2.439(4) . ?
C7 C8 1.368(12) . ?

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
C15 C16 C17 119.1(7) . . ?
C18 C17 C16 121.2(7) . . ?
C17 C18 C19 120.0(7) . . ?
C18 C19 C20 119.3(7) . . ?
C15 C20 C19 122.1(6) . . ?
C16 C15 C14 122.3(6) . . ?
C20 C15 C16 118.3(6) . . ?
C20 C15 C14 119.3(5) . . ?
C13 C14 C15 120.5(5) . . ?
O3 C14 C15 117.2(5) . . ?
O3 C14 C13 122.3(5) . . ?
C12 C13 C14 122.9(6) . . ?
C13 C12 C11 119.5(6) . . ?
O4 C12 C13 127.5(6) . . ?
O4 C12 C11 113.0(5) . . ?
F1 C11 C12 112.3(6) . . ?
F1 C11 F3 106.5(7) . . ?
F2 C11 C12 110.9(6) . . ?
F2 C11 F1 105.7(7) . . ?
F2 C11 F3 106.7(7) . . ?
F3 C11 C12 114.2(6) . . ?
F6 C1 C2 114.6(6) . . ?
F6 C1 F7 107.8(7) . . ?
F6 C1 F8 106.4(7) . . ?
F7 C1 C2 113.0(5) . . ?
F7 C1 F8 104.0(7) . . ?
F8 C1 C2 110.3(6) . . ?
C3 C2 C1 117.4(5) . . ?
O2 C2 C1 114.1(5) . . ?
O2 C2 C3 128.5(5) . . ?
C2 C3 C4 124.0(5) . . ?
C3 C4 C5 119.2(5) . . ?
O1 C4 C3 123.5(5) . . ?
O1 C4 C5 117.3(5) . . ?
C6 C5 C4 121.2(6) . . ?
C10 C5 C4 119.3(6) . . ?
C10 C5 C6 119.5(6) . . ?
C7 C6 C5 118.7(7) . . ?
C5 C10 C9 120.7(8) . . ?
C8 C9 C10 120.4(8) . . ?
C23 C24 C22 121.1(5) . 2_666 ?
F5 C24 C23 120.3(5) . . ?
F5 C24 C22 118.6(5) . 2_666 ?
C24 C23 C22 121.5(5) . . ?
F4 C23 C24 119.3(5) . . ?
F4 C23 C22 119.2(5) . . ?
C24 C22 C21 120.7(5) 2_666 . ?
C23 C22 C24 117.3(5) . 2_666 ?
C23 C22 C21 122.0(5) . . ?
C22 C21 Eu1 170.5(4) . 2_766 ?
O5 C21 C22 118.0(5) . . ?
O5 C21 Eu1 71.3(3) . 2_766 ?
O6 C21 C22 118.2(5) . . ?
O6 C21 O5 123.7(5) . . ?
O6 C21 Eu1 52.4(3) . 2_766 ?
C4 O1 Eu1 132.6(4) . . ?
C2 O2 Eu1 129.0(3) . . ?
C14 O3 Eu1 139.7(4) . . ?
C12 O4 Eu1 136.6(4) . . ?
C21 O5 Eu1 155.6(4) . . ?
C21 O5 Eu1 84.6(3) . 2_766 ?
Eu1 O5 Eu1 119.57(13) . 2_766 ?
C21 O6 Eu1 104.4(3) . 2_766 ?
C25 O7 Eu1 130.0(4) . . ?
C26 O8 Eu1 132.2(4) . . ?
O1 Eu1 C21 140.41(14) . 2_766 ?
O1 Eu1 O2 71.75(14) . . ?
O1 Eu1 O5 83.06(13) . . ?
O1 Eu1 O5 127.57(13) . 2_766 ?
O1 Eu1 O6 144.09(14) . 2_766 ?
O1 Eu1 O7 67.33(14) . . ?
O1 Eu1 O8 137.31(14) . . ?
O2 Eu1 C21 69.03(14) . 2_766 ?
O2 Eu1 O5 79.05(13) . . ?
O2 Eu1 O5 65.69(11) . 2_766 ?
O2 Eu1 O6 76.67(14) . 2_766 ?
O2 Eu1 O7 136.06(14) . . ?
O2 Eu1 O8 131.45(12) . . ?
O3 Eu1 C21 98.93(14) . 2_766 ?
O3 Eu1 O1 75.24(14) . . ?
O3 Eu1 O2 74.31(13) . . ?
O3 Eu1 O5 149.75(13) . . ?
O3 Eu1 O5 118.52(12) . 2_766 ?
O3 Eu1 O6 80.20(14) . 2_766 ?
O3 Eu1 O7 109.04(15) . . ?
O3 Eu1 O8 138.97(13) . . ?
O4 Eu1 C21 99.03(15) . 2_766 ?
O4 Eu1 O1 114.80(15) . . ?
O4 Eu1 O2 140.49(14) . . ?
O4 Eu1 O3 70.56(13) . . ?
O4 Eu1 O5 138.96(13) . . ?
O4 Eu1 O5 117.43(12) . 2_766 ?
O4 Eu1 O6 80.07(14) . 2_766 ?
O4 Eu1 O7 73.95(16) . . ?
O4 Eu1 O8 72.00(13) . . ?
O5 Eu1 C21 24.06(12) 2_766 2_766 ?
O5 Eu1 C21 84.45(14) . 2_766 ?
O5 Eu1 O5 60.43(13) . 2_766 ?
O5 Eu1 O6 107.47(12) . 2_766 ?
O5 Eu1 O7 80.78(15) . . ?
O5 Eu1 O8 70.66(13) . . ?
O6 Eu1 C21 23.14(13) 2_766 2_766 ?
O6 Eu1 O5 47.19(11) 2_766 2_766 ?
O7 Eu1 C21 146.28(15) . 2_766 ?
O7 Eu1 O5 132.27(13) . 2_766 ?
O7 Eu1 O6 147.03(15) . 2_766 ?
O8 Eu1 C21 71.03(14) . 2_766 ?
O8 Eu1 O5 66.50(12) . 2_766 ?
O8 Eu1 O6 77.42(14) . 2_766 ?
O8 Eu1 O7 75.50(14) . . ?
C8 C7 C6 121.1(8) . . ?
C7 C8 C9 119.6(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_10-yb
_database_code_depnum_ccdc_archive 'CCDC 1569946'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H15 F8 O7 Yb'
_chemical_formula_sum            'C25 H15 F8 O7 Yb'
_chemical_formula_weight         753.43
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Yb Yb -0.3850 5.5486 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.023(5)
_cell_length_b                   10.431(5)
_cell_length_c                   13.814(5)
_cell_angle_alpha                90.040(5)
_cell_angle_beta                 102.535(5)
_cell_angle_gamma                109.571(5)
_cell_volume                     1324.1(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4056
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5854
_cell_measurement_theta_min      3.0624
_shelx_estimated_absorpt_T_max   0.545
_shelx_estimated_absorpt_T_min   0.502
_exptl_absorpt_coefficient_mu    3.630
_exptl_absorpt_correction_T_max  0.502
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.887
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             726
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0559
_diffrn_reflns_av_unetI/netI     0.0672
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8987
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.068
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4107
_reflns_number_total             4647
_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       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.016
_refine_diff_density_min         -1.204
_refine_diff_density_rms         0.196
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4647
_refine_ls_number_restraints     349
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0525
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0839P)²+4.7842P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1405
_refine_ls_wR_factor_ref         0.1519
_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, All Yb(H) groups
2. Restrained distances
 C1-F1
 1.392 with sigma of 0.02
 C1-F2
 1.392 with sigma of 0.02
 C1-F3
 1.392 with sigma of 0.02
 O5-H5
 0.85 with sigma of 0.01
 F1-F2
 2.273 with sigma of 0.04
 F1-F3
 2.273 with sigma of 0.04
 F2-F3
 2.273 with sigma of 0.04
 C25-H5
 1.914811 with sigma of 0.02
 Yb01-H5
 2.845342 with sigma of 0.02
3. Rigid bond restraints
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5A, C6A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C4, C5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F1, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15A, C16A, C17A, C18A, C19A, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C1, F3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 3.8A with sigma of
0.04 and sigma for terminal atoms of 0.08
C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim C10A: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim C20A: within 3.8A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C25 \\sim O5: within 3.8A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C5A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(O5)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: C5(0.5) C6(0.5) H6(0.5) C7(0.5) C8(0.5) C9(0.5) C10(0.5) C5A(0.5)
 C6A(0.5) H6A(0.5) C7A(0.5) C8A(0.5) C9A(0.5) C10A(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5)
 H20(0.5) C15A(0.5) C16A(0.5) H16A(0.5) C17A(0.5) H17A(0.5) C18A(0.5) H18A(0.5)
 C19A(0.5) H19A(0.5) C20A(0.5) H20A(0.5)
6.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C6A(H6A), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20), C16A(H16A), C17A(H17A), C18A(H18A),
 C19A(H19A), C20A(H20A)
6.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C5A(C6A,C7A,C8A,C9A,C10A), C15(C16,C17,C18,C19,C20),
 C15A(C16A,C17A,C18A,C19A,C20A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.2311(19) 0.2582(17) 0.8945(10) 0.116(6) Uani 1 1 d D U . . .
C2 C 0.2567(16) 0.3682(14) 0.8175(9) 0.072(4) Uani 1 1 d . . . . .
C3 C 0.3910(15) 0.4627(18) 0.8242(11) 0.084(4) Uani 1 1 d . . . . .
H3 H 0.467181 0.462133 0.876197 0.101 Uiso 1 1 calc R . . . .
C4 C 0.4182(13) 0.5618(15) 0.7544(10) 0.070(4) Uani 1 1 d . U . . .
C5 C 0.5648(13) 0.635(2) 0.7664(17) 0.073(7) Uani 0.5 1 d . U P A 1
C6 C 0.5957(15) 0.728(2) 0.6954(16) 0.075(7) Uani 0.5 1 d G U P A 1
H6 H 0.520336 0.739727 0.647532 0.090 Uiso 0.5 1 calc R . P A 1
C7 C 0.7393(18) 0.805(2) 0.6961(17) 0.114(9) Uani 0.5 1 d G U P A 1
H7 H 0.759995 0.867242 0.648686 0.136 Uiso 1 1 calc R . . A 1
C8 C 0.8520(13) 0.788(3) 0.768(2) 0.115(9) Uani 0.5 1 d G U P A 1
H8 H 0.948025 0.839202 0.768199 0.138 Uiso 1 1 calc R . . A 1
C9 C 0.8210(15) 0.695(3) 0.8387(18) 0.109(9) Uani 0.5 1 d G U P A 1
H9 H 0.896396 0.683646 0.886559 0.130 Uiso 1 1 calc R . . A 1
C10 C 0.6774(17) 0.618(2) 0.8380(16) 0.087(7) Uani 0.5 1 d G U P A 1
C5A C 0.567(3) 0.675(3) 0.749(3) 0.099(8) Uani 0.5 1 d . U P A 2
C6A C 0.570(3) 0.782(3) 0.689(3) 0.122(10) Uani 0.5 1 d G U P A 2
H6A H 0.482861 0.791979 0.655390 0.146 Uiso 0.5 1 calc R . P A 2
C7A C 0.702(3) 0.876(3) 0.680(2) 0.133(10) Uani 0.5 1 d G U P A 2
C8A C 0.831(3) 0.861(3) 0.730(3) 0.131(10) Uani 0.5 1 d G U P A 2
C9A C 0.829(3) 0.753(4) 0.790(3) 0.135(10) Uani 0.5 1 d G U P A 2
C10A C 0.696(3) 0.660(3) 0.799(2) 0.103(8) Uani 0.5 1 d G U P A 2
C11 C 0.266(3) 0.9607(17) 0.6372(13) 0.126(9) Uani 1 1 d . . . . .
C12 C 0.2107(14) 0.8293(12) 0.6844(9) 0.065(3) Uani 1 1 d . . . . .
C13 C 0.2481(14) 0.8345(12) 0.7846(9) 0.066(3) Uani 1 1 d . . . . .
H13 H 0.312447 0.915934 0.819218 0.080 Uiso 1 1 calc R . . . .
C14 C 0.1935(10) 0.7211(11) 0.8402(7) 0.044(2) Uani 1 1 d . . . . .
C15 C 0.228(2) 0.726(2) 0.9501(11) 0.043(7) Uani 0.5 1 d . . P B 1
C16 C 0.1249(19) 0.641(2) 0.9966(17) 0.100(12) Uani 0.5 1 d G U P B 1
H16 H 0.037275 0.581843 0.958674 0.120 Uiso 0.5 1 calc R . P B 1
C17 C 0.153(3) 0.646(3) 1.0998(17) 0.15(2) Uani 0.5 1 d G . P B 1
H17 H 0.084132 0.589031 1.130976 0.174 Uiso 0.5 1 calc R . P B 1
C18 C 0.284(3) 0.734(3) 1.1566(11) 0.077(10) Uani 0.5 1 d G . P B 1
H18 H 0.302717 0.737131 1.225630 0.092 Uiso 0.5 1 calc R . P B 1
C19 C 0.387(2) 0.819(3) 1.1100(13) 0.120(15) Uani 0.5 1 d G . P B 1
H19 H 0.474447 0.878044 1.147983 0.144 Uiso 0.5 1 calc R . P B 1
C20 C 0.3588(19) 0.814(2) 1.0068(13) 0.090(10) Uani 0.5 1 d G . P B 1
H20 H 0.427594 0.870858 0.975681 0.108 Uiso 0.5 1 calc R . P B 1
C15A C 0.224(2) 0.7458(16) 0.9512(8) 0.047(7) Uani 0.5 1 d . U P B 2
C16A C 0.195(2) 0.6308(14) 1.0048(11) 0.052(5) Uani 0.5 1 d G U P B 2
H16A H 0.157251 0.544173 0.971597 0.062 Uiso 0.5 1 calc R . P B 2
C17A C 0.221(2) 0.6453(18) 1.1079(11) 0.065(6) Uani 0.5 1 d G U P B 2
H17A H 0.201773 0.568390 1.143765 0.078 Uiso 0.5 1 calc R . P B 2
C18A C 0.277(3) 0.775(2) 1.1575(8) 0.074(7) Uani 0.5 1 d G U P B 2
H18A H 0.294834 0.784501 1.226479 0.088 Uiso 0.5 1 calc R . P B 2
C19A C 0.306(2) 0.8898(16) 1.1039(11) 0.071(5) Uani 0.5 1 d G U P B 2
H19A H 0.343373 0.976397 1.137026 0.085 Uiso 0.5 1 calc R . P B 2
C20A C 0.279(2) 0.8753(14) 1.0007(11) 0.062(5) Uani 0.5 1 d G U P B 2
H20A H 0.298853 0.952184 0.964857 0.074 Uiso 0.5 1 calc R . P B 2
C21 C 0.2067(9) 0.5053(9) 0.4305(6) 0.0342(19) Uani 1 1 d . . . . .
C22 C 0.3560(9) 0.5015(9) 0.4664(6) 0.0353(19) Uani 1 1 d . . . . .
C23 C 0.3838(9) 0.4015(9) 0.5229(7) 0.037(2) Uani 1 1 d . . . . .
C24 C 0.5233(10) 0.3977(10) 0.5565(7) 0.042(2) Uani 1 1 d . . . . .
C25 C -0.126(4) 0.162(3) 0.631(2) 0.27(2) Uani 1 1 d D U . . .
H25A H -0.169673 0.082923 0.584095 0.401 Uiso 1 1 calc R . . . .
H25B H -0.058241 0.144294 0.685422 0.401 Uiso 1 1 calc R . . . .
H25C H -0.200265 0.181208 0.655469 0.401 Uiso 1 1 calc R . . . .
F1 F 0.156(4) 0.1300(17) 0.8467(17) 0.39(2) Uani 1 1 d D U . . .
F2 F 0.3584(17) 0.247(2) 0.9494(11) 0.208(8) Uani 1 1 d D . . . .
F3 F 0.127(2) 0.259(3) 0.9424(16) 0.252(11) Uani 1 1 d D U . . .
F4 F 0.158(2) 0.9867(11) 0.5751(10) 0.184(8) Uani 1 1 d . . . . .
F5 F 0.345(2) 1.0637(12) 0.6956(9) 0.253(12) Uani 1 1 d . . . . .
F6 F 0.3453(19) 0.9513(16) 0.5777(13) 0.199(8) Uani 1 1 d . . . . .
F7 F 0.2742(6) 0.3029(7) 0.5461(5) 0.0664(19) Uani 1 1 d . . . . .
F8 F 0.5400(7) 0.2936(7) 0.6075(6) 0.072(2) Uani 1 1 d . . . . .
O1 O 0.1172(7) 0.6067(7) 0.7991(5) 0.0445(15) Uani 1 1 d . . . . .
O4 O 0.1405(9) 0.3579(8) 0.7563(5) 0.060(2) Uani 1 1 d . . . . .
O5 O -0.0498(8) 0.2780(7) 0.5822(5) 0.0515(17) Uani 1 1 d D U . . .
O3 O 0.3211(7) 0.5754(9) 0.6844(5) 0.0573(19) Uani 1 1 d . . . . .
O6 O 0.1257(6) 0.4880(6) 0.4909(4) 0.0342(13) Uani 1 1 d . . . . .
O7 O 0.1626(7) 0.5226(7) 0.3410(5) 0.0451(16) Uani 1 1 d . . . . .
O2 O 0.1348(8) 0.7264(7) 0.6211(5) 0.0496(17) Uani 1 1 d . . . . .
Yb01 Yb 0.07972(3) 0.49961(4) 0.64689(2) 0.03283(17) Uani 1 1 d D . . . .
H5 H -0.034(8) 0.248(3) 0.530(4) 0.049 Uiso 1 1 d DR . . . .


_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 1.56(2) . ?
C1 F1 1.378(16) . ?
C1 F2 1.379(14) . ?
C1 F3 1.357(16) . ?
C2 C3 1.36(2) . ?
C2 O4 1.253(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.41(2) . ?
C4 C5 1.383(17) . ?
C4 C5A 1.58(3) . ?
C4 O3 1.260(14) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C11 C12 1.504(19) . ?
C11 F4 1.33(3) . ?
C11 F5 1.258(18) . ?
C11 F6 1.28(3) . ?
C12 C13 1.349(16) . ?
C12 O2 1.287(14) . ?
C13 H13 0.9300 . ?
C13 C14 1.427(16) . ?
C14 C15 1.480(17) . ?
C14 C15A 1.502(14) . ?
C14 O1 1.237(12) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C19A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C20A 1.3900 . ?
C20A H20A 0.9300 . ?
C21 C22 1.485(12) . ?
C21 O6 1.259(10) . ?
C21 O7 1.254(11) . ?
C21 Yb01 2.821(8) 2_566 ?
C22 C23 1.370(13) . ?
C22 C24 1.408(12) 2_666 ?
C23 C24 1.389(12) . ?
C23 F7 1.328(10) . ?
C24 F8 1.331(11) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O5 1.45(2) . ?
O1 Yb01 2.276(7) . ?
O4 Yb01 2.246(7) . ?
O5 Yb01 2.304(7) . ?
O5 H5 0.854(10) . ?
O3 Yb01 2.218(7) . ?
O6 Yb01 2.310(6) . ?
O6 Yb01 2.521(5) 2_566 ?
O7 Yb01 2.404(6) 2_566 ?
O2 Yb01 2.289(7) . ?
Yb01 Yb01 4.0269(15) 2_566 ?

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 110.6(14) . . ?
F1 C1 F2 103.8(16) . . ?
F2 C1 C2 113.2(15) . . ?
F3 C1 C2 113.4(13) . . ?
F3 C1 F1 95.1(19) . . ?
F3 C1 F2 118.4(15) . . ?
C3 C2 C1 120.7(11) . . ?
O4 C2 C1 111.4(13) . . ?
O4 C2 C3 127.9(13) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(11) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5A 128.7(16) . . ?
C5 C4 C3 112.7(13) . . ?
O3 C4 C3 123.8(12) . . ?
O3 C4 C5 123.3(16) . . ?
O3 C4 C5A 107.5(17) . . ?
C4 C5 C6 114.0(13) . . ?
C4 C5 C10 125.9(13) . . ?
C6 C5 C10 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.0 . . ?
C10 C9 H9 120.0 . . ?
C9 C10 C5 120.0 . . ?
C6A C5A C4 121(2) . . ?
C6A C5A C10A 120.0 . . ?
C10A C5A C4 119(2) . . ?
C5A C6A H6A 120.0 . . ?
C5A C6A C7A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
F4 C11 C12 111.4(18) . . ?
F5 C11 C12 116.3(14) . . ?
F5 C11 F4 111(2) . . ?
F5 C11 F6 104(2) . . ?
F6 C11 C12 111(2) . . ?
F6 C11 F4 101.1(16) . . ?
C13 C12 C11 116.9(12) . . ?
O2 C12 C11 113.6(11) . . ?
O2 C12 C13 129.5(11) . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(11) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 124.3(11) . . ?
C13 C14 C15A 118.0(11) . . ?
O1 C14 C13 121.9(9) . . ?
O1 C14 C15 113.7(11) . . ?
O1 C14 C15A 120.0(10) . . ?
C16 C15 C14 118.8(13) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C14 121.2(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.00(6) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C16A C15A C14 116.6(10) . . ?
C16A C15A C20A 120.0 . . ?
C20A C15A C14 123.4(10) . . ?
C15A C16A H16A 120.0 . . ?
C15A C16A C17A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C15A C20A H20A 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C22 C21 Yb01 176.5(6) . 2_566 ?
O6 C21 C22 118.7(8) . . ?
O6 C21 Yb01 63.4(4) . 2_566 ?
O7 C21 C22 119.9(8) . . ?
O7 C21 O6 121.3(8) . . ?
O7 C21 Yb01 58.0(4) . 2_566 ?
C23 C22 C21 122.4(8) . . ?
C23 C22 C24 116.8(8) . 2_666 ?
C24 C22 C21 120.8(8) 2_666 . ?
C22 C23 C24 122.5(8) . . ?
F7 C23 C22 119.5(7) . . ?
F7 C23 C24 117.9(8) . . ?
C23 C24 C22 120.7(8) . 2_666 ?
F8 C24 C22 120.6(8) . 2_666 ?
F8 C24 C23 118.6(8) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
C14 O1 Yb01 134.7(6) . . ?
C2 O4 Yb01 132.2(9) . . ?
C25 O5 Yb01 129.2(14) . . ?
C25 O5 H5 108(2) . . ?
Yb01 O5 H5 119.6(19) . . ?
C4 O3 Yb01 135.3(9) . . ?
C21 O6 Yb01 154.2(6) . . ?
C21 O6 Yb01 90.1(5) . 2_566 ?
Yb01 O6 Yb01 112.9(2) . 2_566 ?
C21 O7 Yb01 95.7(5) . 2_566 ?
C12 O2 Yb01 127.6(7) . . ?
C21 Yb01 Yb01 58.08(18) 2_566 2_566 ?
O1 Yb01 C21 98.1(2) . 2_566 ?
O1 Yb01 O5 131.9(2) . . ?
O1 Yb01 O6 119.0(2) . 2_566 ?
O1 Yb01 O6 152.9(2) . . ?
O1 Yb01 O7 77.2(2) . 2_566 ?
O1 Yb01 O2 74.7(2) . . ?
O1 Yb01 Yb01 144.51(17) . 2_566 ?
O4 Yb01 C21 124.8(3) . 2_566 ?
O4 Yb01 O1 75.1(3) . . ?
O4 Yb01 O5 71.4(3) . . ?
O4 Yb01 O6 141.7(2) . 2_566 ?
O4 Yb01 O6 117.7(2) . . ?
O4 Yb01 O7 103.5(3) . 2_566 ?
O4 Yb01 O2 141.8(3) . . ?
O4 Yb01 Yb01 139.3(2) . 2_566 ?
O5 Yb01 C21 74.9(3) . 2_566 ?
O5 Yb01 O6 74.0(2) . 2_566 ?
O5 Yb01 O6 74.9(2) . . ?
O5 Yb01 O7 78.2(3) . 2_566 ?
O5 Yb01 Yb01 71.22(17) . 2_566 ?
O3 Yb01 C21 159.3(3) . 2_566 ?
O3 Yb01 O1 81.7(3) . . ?
O3 Yb01 O4 75.3(3) . . ?
O3 Yb01 O5 120.5(3) . . ?
O3 Yb01 O6 79.2(2) . . ?
O3 Yb01 O6 138.6(2) . 2_566 ?
O3 Yb01 O7 158.3(3) . 2_566 ?
O3 Yb01 O2 77.7(3) . . ?
O3 Yb01 Yb01 111.24(19) . 2_566 ?
O6 Yb01 C21 26.5(2) 2_566 2_566 ?
O6 Yb01 C21 93.1(2) . 2_566 ?
O6 Yb01 O6 67.1(2) . 2_566 ?
O6 Yb01 O7 118.7(2) . 2_566 ?
O6 Yb01 Yb01 35.24(14) . 2_566 ?
O6 Yb01 Yb01 31.91(13) 2_566 2_566 ?
O7 Yb01 C21 26.3(2) 2_566 2_566 ?
O7 Yb01 O6 52.8(2) 2_566 2_566 ?
O7 Yb01 Yb01 84.07(15) 2_566 2_566 ?
O2 Yb01 C21 82.3(2) . 2_566 ?
O2 Yb01 O5 146.6(2) . . ?
O2 Yb01 O6 82.5(2) . . ?
O2 Yb01 O6 74.7(2) . 2_566 ?
O2 Yb01 O7 92.0(3) . 2_566 ?
O2 Yb01 Yb01 76.10(16) . 2_566 ?

_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_3-nd_sq
_database_code_depnum_ccdc_archive 'CCDC 1569939'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F8 Nd O8 [+ C H4 O]'
_chemical_formula_sum            'C26 H20 F8 Nd O8 [+ C H4 O]'
_chemical_formula_weight         756.66
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -0.1943 3.0179 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.014(5)
_cell_length_b                   11.412(5)
_cell_length_c                   14.972(5)
_cell_angle_alpha                102.528(5)
_cell_angle_beta                 96.725(5)
_cell_angle_gamma                114.790(5)
_cell_volume                     1474.0(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4215
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7154
_cell_measurement_theta_min      3.2237
_shelx_estimated_absorpt_T_max   0.708
_shelx_estimated_absorpt_T_min   0.664
_exptl_absorpt_coefficient_mu    1.857
_exptl_absorpt_correction_T_max  0.690
_exptl_absorpt_correction_T_min  0.647
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.705
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             744
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_av_unetI/netI     0.0979
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9571
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.230
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4324
_reflns_number_total             5178
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
 From the SQUEEZE data output we see that the contribution of some 41 electrons were removed the unit cell by the SQUEEZE process. With methanol having 18 electrons, this 41 electron value could be in accord with the contribution of some 2.3 MeOH molecules being removed from the unit cell (or 1.1 MeOH molecules per asymmetric unit).
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         3.051
_refine_diff_density_min         -1.742
_refine_diff_density_rms         0.187
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5178
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0737
_refine_ls_R_factor_gt           0.0648
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1021P)²+0.9684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1735
_refine_ls_wR_factor_ref         0.1865
_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, All O(H) groups
2. Restrained distances
 C26-O8
 1.45 with sigma of 0.02
 C25-O7
 1.45 with sigma of 0.02
 O8-H8A
 0.85 with sigma of 0.01
 O7-H7A
 0.85 with sigma of 0.01
 C26-Nd1
 3.61 with sigma of 0.04
 C25-Nd1
 3.61 with sigma of 0.04
 C26-H8A
 1.973657 with sigma of 0.02
 Nd1-H8A
 3.004347 with sigma of 0.02
 C25-H7A
 1.914152 with sigma of 0.02
 Nd1-H7A
 3.118257 with sigma of 0.02
3. Rigid bond restraints
 O8, C26
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O7, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O8 \\sim C26: within 3.8A with sigma of 0.04 and sigma for terminal atoms of
0.08
O7 \\sim C25: within 3.8A with sigma of 0.04 and sigma for terminal atoms of
0.08
5.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.2975(14) 0.9112(11) 0.7692(7) 0.063(3) Uani 1 1 d . . . . .
C2 C 1.1402(11) 0.7859(8) 0.7425(6) 0.042(2) Uani 1 1 d . . . . .
C3 C 1.0390(12) 0.7947(9) 0.7900(6) 0.044(2) Uani 1 1 d . . . . .
H3 H 1.068061 0.874017 0.837702 0.052 Uiso 1 1 calc R . . . .
C4 C 0.8870(10) 0.6885(9) 0.7718(6) 0.0401(19) Uani 1 1 d . . . . .
C5 C 0.7843(11) 0.7116(10) 0.8316(6) 0.045(2) Uani 1 1 d . . . . .
C6 C 0.8407(13) 0.8056(10) 0.9210(7) 0.056(3) Uani 1 1 d . . . . .
H6 H 0.944301 0.858590 0.945679 0.068 Uiso 1 1 calc R . . . .
C7 C 0.7372(17) 0.8174(13) 0.9718(9) 0.081(4) Uani 1 1 d . . . . .
H7 H 0.773343 0.876244 1.032642 0.097 Uiso 1 1 calc R . . . .
C8 C 0.5866(17) 0.7471(14) 0.9365(10) 0.086(4) Uani 1 1 d . . . . .
H8 H 0.520355 0.758841 0.971856 0.103 Uiso 1 1 calc R . . . .
C9 C 0.5324(17) 0.6580(16) 0.8479(10) 0.094(4) Uani 1 1 d . . . . .
H9 H 0.428692 0.611814 0.822119 0.113 Uiso 1 1 calc R . . . .
C10 C 0.6300(14) 0.6356(12) 0.7958(8) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.591813 0.570151 0.737565 0.080 Uiso 1 1 calc R . . . .
C11 C 0.9226(19) 0.0810(12) 0.7459(9) 0.079(4) Uani 1 1 d . . . . .
C12 C 0.9719(12) 0.2384(9) 0.7590(7) 0.049(2) Uani 1 1 d . . . . .
C13 C 1.0593(13) 0.3305(10) 0.8422(7) 0.057(3) Uani 1 1 d . . . . .
H13 H 1.095101 0.301883 0.889014 0.068 Uiso 1 1 calc R . . . .
C14 C 1.0982(11) 0.4697(9) 0.8601(6) 0.044(2) Uani 1 1 d . . . . .
C15 C 1.1820(11) 0.5705(9) 0.9580(6) 0.046(2) Uani 1 1 d . . . . .
C16 C 1.2288(17) 0.5304(13) 1.0302(8) 0.078(4) Uani 1 1 d . . . . .
H16 H 1.212468 0.441723 1.020647 0.094 Uiso 1 1 calc R . . . .
C17 C 1.3026(17) 0.6270(12) 1.1195(8) 0.084(4) Uani 1 1 d . . . . .
H17 H 1.337668 0.601614 1.168569 0.101 Uiso 1 1 calc R . . . .
C18 C 1.3238(15) 0.7578(13) 1.1356(8) 0.073(3) Uani 1 1 d . . . . .
H18 H 1.371531 0.820344 1.194918 0.087 Uiso 1 1 calc R . . . .
C19 C 1.2741(15) 0.7923(12) 1.0641(7) 0.067(3) Uani 1 1 d . . . . .
H19 H 1.287591 0.880277 1.074246 0.081 Uiso 1 1 calc R . . . .
C20 C 1.2015(14) 0.6996(11) 0.9730(7) 0.059(3) Uani 1 1 d . . . . .
H20 H 1.167589 0.726240 0.924267 0.071 Uiso 1 1 calc R . . . .
C21 C 0.7747(10) 0.5246(9) 0.4414(6) 0.0379(19) Uani 1 1 d . . . . .
C22 C 0.6326(10) 0.5116(8) 0.4714(5) 0.0353(18) Uani 1 1 d . . . . .
C23 C 0.6285(10) 0.6224(8) 0.5301(6) 0.0375(18) Uani 1 1 d . . . . .
C24 C 0.5001(10) 0.6108(8) 0.5574(6) 0.0376(18) Uani 1 1 d . . . . .
C25 C 0.575(3) 0.1530(17) 0.572(3) 0.31(2) Uani 1 1 d D U . . .
H25A H 0.470155 0.125606 0.570531 0.459 Uiso 1 1 calc R . . . .
H25B H 0.586644 0.124181 0.509420 0.459 Uiso 1 1 calc R . . . .
H25C H 0.612976 0.112730 0.611807 0.459 Uiso 1 1 calc R . . . .
C26 C 0.878(4) 0.115(3) 0.483(3) 0.284(19) Uani 1 1 d D U . . .
H26A H 0.830667 0.056754 0.419296 0.425 Uiso 1 1 calc R . . . .
H26B H 0.983569 0.138328 0.495941 0.425 Uiso 1 1 calc R . . . .
H26C H 0.830948 0.069053 0.525665 0.425 Uiso 1 1 calc R . . . .
O1 O 0.8315(7) 0.5773(6) 0.7092(4) 0.0432(14) Uani 1 1 d . . . . .
O2 O 1.1232(8) 0.6881(6) 0.6731(4) 0.0450(15) Uani 1 1 d . . . . .
O3 O 1.0630(8) 0.5168(6) 0.7980(4) 0.0444(15) Uani 1 1 d . . . . .
O4 O 0.9148(8) 0.2512(6) 0.6846(4) 0.0505(16) Uani 1 1 d . . . . .
O5 O 0.8626(6) 0.4968(6) 0.4882(4) 0.0378(13) Uani 1 1 d . . . . .
O6 O 0.7991(7) 0.5638(7) 0.3702(4) 0.0488(16) Uani 1 1 d . . . . .
O7 O 0.6611(9) 0.3012(7) 0.6091(5) 0.0628(19) Uani 1 1 d D U . . .
H7A H 0.607(4) 0.329(4) 0.639(6) 0.094 Uiso 1 1 d DR . . . .
O8 O 0.8595(9) 0.2436(6) 0.4937(4) 0.0565(18) Uani 1 1 d D U . . .
H8A H 0.846(11) 0.254(4) 0.4390(9) 0.085 Uiso 1 1 d DR . . . .
Nd1 Nd 0.94677(5) 0.44454(4) 0.63273(3) 0.0314(2) Uani 1 1 d D . . . .
F1 F 0.7754(15) 0.0061(8) 0.7184(8) 0.137(4) Uani 1 1 d . . . . .
F2 F 0.9818(16) 0.0348(9) 0.6865(8) 0.140(4) Uani 1 1 d . . . . .
F3 F 0.9627(15) 0.0636(8) 0.8275(6) 0.139(4) Uani 1 1 d . . . . .
F4 F 0.7554(7) 0.7416(6) 0.5602(5) 0.0668(17) Uani 1 1 d . . . . .
F5 F 0.4994(7) 0.7202(5) 0.6139(4) 0.0645(16) Uani 1 1 d . . . . .
F6 F 1.3231(12) 1.0118(10) 0.8317(9) 0.194(7) Uani 1 1 d . . . . .
F7 F 1.3443(13) 0.9456(13) 0.7010(7) 0.185(7) Uani 1 1 d . . . . .
F8 F 1.3992(13) 0.8756(15) 0.7996(15) 0.222(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
C1 C2 1.550(15) . ?
C1 F6 1.221(12) . ?
C1 F7 1.244(12) . ?
C1 F8 1.315(17) . ?
C2 C3 1.328(12) . ?
C2 O2 1.285(10) . ?
C3 C4 1.440(13) . ?
C4 C5 1.507(11) . ?
C4 O1 1.252(10) . ?
C5 C6 1.398(14) . ?
C5 C10 1.381(16) . ?
C6 C7 1.389(15) . ?
C7 C8 1.346(19) . ?
C8 C9 1.368(19) . ?
C9 C10 1.388(16) . ?
C11 C12 1.609(14) . ?
C11 F1 1.312(18) . ?
C11 F2 1.266(17) . ?
C11 F3 1.323(14) . ?
C12 C13 1.352(14) . ?
C12 O4 1.256(11) . ?
C13 C14 1.422(13) . ?
C14 C15 1.531(13) . ?
C14 O3 1.255(10) . ?
C15 C16 1.369(14) . ?
C15 C20 1.366(13) . ?
C16 C17 1.412(17) . ?
C17 C18 1.378(17) . ?
C18 C19 1.332(17) . ?
C19 C20 1.415(15) . ?
C21 C22 1.500(11) . ?
C21 O5 1.246(10) . ?
C21 O6 1.255(10) . ?
C21 Nd1 3.034(8) 2_766 ?
C22 C23 1.393(11) . ?
C22 C24 1.397(12) 2_666 ?
C23 C24 1.358(11) . ?
C23 F4 1.349(10) . ?
C24 F5 1.350(9) . ?
C25 O7 1.472(15) . ?
C26 O8 1.532(16) . ?
O1 Nd1 2.442(5) . ?
O2 Nd1 2.473(6) . ?
O3 Nd1 2.407(6) . ?
O4 Nd1 2.406(6) . ?
O5 Nd1 2.511(5) . ?
O5 Nd1 2.763(5) 2_766 ?
O6 Nd1 2.591(6) 2_766 ?
O7 Nd1 2.563(8) . ?
O8 Nd1 2.486(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
F6 C1 C2 119.6(9) . . ?
F6 C1 F7 109.1(13) . . ?
F6 C1 F8 103.8(15) . . ?
F7 C1 C2 114.5(10) . . ?
F7 C1 F8 99.4(14) . . ?
F8 C1 C2 107.9(10) . . ?
C3 C2 C1 117.2(8) . . ?
O2 C2 C1 114.4(8) . . ?
O2 C2 C3 128.4(9) . . ?
C2 C3 C4 123.8(8) . . ?
C3 C4 C5 118.2(8) . . ?
O1 C4 C3 125.2(8) . . ?
O1 C4 C5 116.6(8) . . ?
C6 C5 C4 122.0(9) . . ?
C10 C5 C4 117.9(9) . . ?
C10 C5 C6 120.0(9) . . ?
C7 C6 C5 117.8(11) . . ?
C8 C7 C6 122.6(12) . . ?
C7 C8 C9 119.1(11) . . ?
C8 C9 C10 121.0(13) . . ?
C5 C10 C9 119.2(11) . . ?
F1 C11 C12 112.3(11) . . ?
F1 C11 F3 105.6(13) . . ?
F2 C11 C12 111.8(11) . . ?
F2 C11 F1 107.8(13) . . ?
F2 C11 F3 109.1(12) . . ?
F3 C11 C12 110.0(10) . . ?
C13 C12 C11 119.3(8) . . ?
O4 C12 C11 109.3(9) . . ?
O4 C12 C13 131.4(8) . . ?
C12 C13 C14 121.9(8) . . ?
C13 C14 C15 121.5(7) . . ?
O3 C14 C13 122.4(8) . . ?
O3 C14 C15 116.1(8) . . ?
C16 C15 C14 120.9(9) . . ?
C20 C15 C14 118.5(8) . . ?
C20 C15 C16 120.6(10) . . ?
C15 C16 C17 118.4(11) . . ?
C18 C17 C16 121.6(11) . . ?
C19 C18 C17 118.1(11) . . ?
C18 C19 C20 122.3(11) . . ?
C15 C20 C19 118.9(10) . . ?
C22 C21 Nd1 175.6(6) . 2_766 ?
O5 C21 C22 118.9(7) . . ?
O5 C21 O6 123.3(7) . . ?
O5 C21 Nd1 65.6(4) . 2_766 ?
O6 C21 C22 117.9(7) . . ?
O6 C21 Nd1 57.7(4) . 2_766 ?
C23 C22 C21 120.8(8) . . ?
C23 C22 C24 117.3(7) . 2_666 ?
C24 C22 C21 121.9(7) 2_666 . ?
C24 C23 C22 120.9(8) . . ?
F4 C23 C22 118.8(7) . . ?
F4 C23 C24 120.3(7) . . ?
C23 C24 C22 121.8(7) . 2_666 ?
F5 C24 C22 118.7(7) . 2_666 ?
F5 C24 C23 119.5(8) . . ?
C4 O1 Nd1 132.0(6) . . ?
C2 O2 Nd1 129.2(5) . . ?
C14 O3 Nd1 139.6(6) . . ?
C12 O4 Nd1 133.0(6) . . ?
C21 O5 Nd1 90.2(5) . 2_766 ?
C21 O5 Nd1 150.6(5) . . ?
Nd1 O5 Nd1 118.6(2) . 2_766 ?
C21 O6 Nd1 98.1(5) . 2_766 ?
C25 O7 Nd1 126.7(12) . . ?
C26 O8 Nd1 130.5(14) . . ?
O1 Nd1 C21 141.6(2) . 2_766 ?
O1 Nd1 O2 70.2(2) . . ?
O1 Nd1 O5 128.76(18) . 2_766 ?
O1 Nd1 O5 84.34(18) . . ?
O1 Nd1 O6 143.8(2) . 2_766 ?
O1 Nd1 O7 68.4(2) . . ?
O1 Nd1 O8 135.3(2) . . ?
O2 Nd1 C21 71.5(2) . 2_766 ?
O2 Nd1 O5 67.07(17) . 2_766 ?
O2 Nd1 O5 79.5(2) . . ?
O2 Nd1 O6 79.4(2) . 2_766 ?
O2 Nd1 O7 136.1(2) . . ?
O2 Nd1 O8 135.85(19) . . ?
O3 Nd1 C21 97.8(2) . 2_766 ?
O3 Nd1 O1 74.6(2) . . ?
O3 Nd1 O2 73.6(2) . . ?
O3 Nd1 O5 150.09(18) . . ?
O3 Nd1 O5 117.2(2) . 2_766 ?
O3 Nd1 O6 78.3(2) . 2_766 ?
O3 Nd1 O7 108.4(2) . . ?
O3 Nd1 O8 138.8(2) . . ?
O4 Nd1 C21 96.2(2) . 2_766 ?
O4 Nd1 O1 115.3(2) . . ?
O4 Nd1 O2 139.7(2) . . ?
O4 Nd1 O3 70.3(2) . . ?
O4 Nd1 O5 139.1(2) . . ?
O4 Nd1 O5 115.50(19) . 2_766 ?
O4 Nd1 O6 76.4(2) . 2_766 ?
O4 Nd1 O7 73.6(2) . . ?
O4 Nd1 O8 70.5(2) . . ?
O5 Nd1 C21 85.5(2) . 2_766 ?
O5 Nd1 C21 24.23(19) 2_766 2_766 ?
O5 Nd1 O5 61.4(2) . 2_766 ?
O5 Nd1 O6 109.55(17) . 2_766 ?
O5 Nd1 O7 82.4(2) . . ?
O6 Nd1 C21 24.2(2) 2_766 2_766 ?
O6 Nd1 O5 48.40(17) 2_766 2_766 ?
O7 Nd1 C21 146.0(2) . 2_766 ?
O7 Nd1 O5 134.0(2) . 2_766 ?
O7 Nd1 O6 144.5(2) . 2_766 ?
O8 Nd1 C21 74.2(2) . 2_766 ?
O8 Nd1 O5 70.8(2) . . ?
O8 Nd1 O5 70.18(19) . 2_766 ?
O8 Nd1 O6 80.6(2) . 2_766 ?
O8 Nd1 O7 71.8(2) . . ?

_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_9-er
_database_code_depnum_ccdc_archive 'CCDC 1569945'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 Er F8 O7'
_chemical_formula_sum            'C25 H16 Er F8 O7'
_chemical_formula_weight         747.64
_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 0.0033 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'
Er Er -0.2586 4.9576 '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'
O O 0.0106 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.041(5)
_cell_length_b                   10.457(5)
_cell_length_c                   13.838(5)
_cell_angle_alpha                89.973(5)
_cell_angle_beta                 77.697(5)
_cell_angle_gamma                70.313(5)
_cell_volume                     1332.6(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4261
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4676
_cell_measurement_theta_min      3.5096
_shelx_estimated_absorpt_T_max   0.716
_shelx_estimated_absorpt_T_min   0.642
_exptl_absorpt_coefficient_mu    3.247
_exptl_absorpt_correction_T_max  0.700
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.863
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8598
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.517
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4242
_reflns_number_total             4674
_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       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         2.207
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.153
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         4674
_refine_ls_number_restraints     251
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0424
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+3.9771P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1167
_refine_ls_wR_factor_ref         0.1199
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups, H5 of C11
 At 1.2 times of:
  H8 of C8, H9 of C9, H10 of C10, H6A of C6A, H10A of C10A, H13 of C13, H16
  of C16, H17 of C17, H18 of C18, H19 of C19, H20 of C20, H7 of C7, H6 of C6,
  H3 of C3, H20A of C20A, H19A of C19A, H18A of C18A, H17A of C17A, H16A of C16A
2. Restrained distances
 O5-H5
 0.85 with sigma of 0.01
 C25-H5
 1.907781 with sigma of 0.02
 Er1-H5
 2.850453 with sigma of 0.02
3. Rigid bond restraints
 C5A, C6A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C14, C15
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim C10A: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 3.8A with sigma of
0.04 and sigma for terminal atoms of 0.08
C25 \\sim O5: within 3.8A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C10) \\sim Ueq, Uanis(C5A) \\sim Ueq, Uanis(C10A) \\sim Ueq, Uanis(C6)
\\sim Ueq, Uanis(C5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(O5) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
5. Others
 Fixed Sof: C5(0.5) C6(0.5) H6(0.5) C7(0.5) C8(0.5) C9(0.5) C10(0.5) H10(0.5)
 C5A(0.5) C6A(0.5) H6A(0.5) C7A(0.5) C8A(0.5) C9A(0.5) C10A(0.5) H10A(0.5)
 C15(0.5) C16(0.5) H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5)
 H19(0.5) C20(0.5) H20(0.5) C15A(0.5) C16A(0.5) H16A(0.5) C17A(0.5) H17A(0.5)
 C18A(0.5) H18A(0.5) C19A(0.5) H19A(0.5) C20A(0.5) H20A(0.5)
6.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6A(H6A), C10A(H10A),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C16A(H16A),
 C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
6.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C5A(C6A,C7A,C8A,C9A,C10A), C15(C16,C17,C18,C19,C20),
 C15A(C16A,C17A,C18A,C19A,C20A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C2 C 0.7445(12) 0.3648(11) 0.8180(6) 0.067(3) Uani 1 1 d . . . . .
C3 C 0.6090(12) 0.4588(13) 0.8251(8) 0.078(3) Uani 1 1 d . . . . .
H3 H 0.533377 0.457321 0.876868 0.094 Uiso 1 1 calc R . . . .
C4 C 0.5811(9) 0.5584(12) 0.7554(7) 0.068(3) Uani 1 1 d . . . . .
C5 C 0.4342(10) 0.6372(14) 0.7674(10) 0.049(4) Uani 0.5 1 d . U P A 1
C6 C 0.4041(13) 0.7294(15) 0.6958(10) 0.061(4) Uani 0.5 1 d G U P A 1
H6 H 0.479777 0.740982 0.648936 0.073 Uiso 0.5 1 calc R . P A 1
C7 C 0.2610(15) 0.8041(18) 0.6943(12) 0.111(7) Uani 0.5 1 d G U P A 1
H7 H 0.240943 0.865785 0.646415 0.134 Uiso 1 1 calc R . . A 1
C8 C 0.1480(11) 0.787(2) 0.7644(15) 0.117(8) Uani 0.5 1 d G U P A 1
H8 H 0.052249 0.836783 0.763410 0.140 Uiso 1 1 calc R . . A 1
C9 C 0.1780(11) 0.695(2) 0.8360(13) 0.104(7) Uani 0.5 1 d G U P A 1
H9 H 0.102387 0.682977 0.882928 0.125 Uiso 1 1 calc R . . A 1
C10 C 0.3211(13) 0.6198(15) 0.8375(10) 0.066(4) Uani 0.5 1 d G U P A 1
H10 H 0.341220 0.558172 0.885451 0.079 Uiso 0.5 1 calc R . P A 1
C5A C 0.4295(19) 0.683(2) 0.744(2) 0.106(7) Uani 0.5 1 d . U P A 2
C6A C 0.422(2) 0.794(3) 0.686(2) 0.129(9) Uani 0.5 1 d G U P A 2
H6A H 0.506468 0.804265 0.650609 0.154 Uiso 0.5 1 calc R . P A 2
C7A C 0.287(3) 0.888(2) 0.682(2) 0.150(9) Uani 0.5 1 d G U P A 2
C8A C 0.161(2) 0.872(3) 0.735(2) 0.142(9) Uani 0.5 1 d G U P A 2
C9A C 0.1684(19) 0.761(3) 0.793(2) 0.148(9) Uani 0.5 1 d G U P A 2
C10A C 0.303(2) 0.667(2) 0.7969(19) 0.108(7) Uani 0.5 1 d G U P A 2
H10A H 0.307978 0.593516 0.835354 0.130 Uiso 0.5 1 calc R . P A 2
C12 C 0.7864(12) 0.8309(10) 0.6851(7) 0.069(3) Uani 1 1 d . . . . .
C13 C 0.7519(11) 0.8347(10) 0.7861(7) 0.069(3) Uani 1 1 d . . . . .
H13 H 0.689131 0.915915 0.821382 0.083 Uiso 1 1 calc R . . . .
C14 C 0.8076(8) 0.7203(8) 0.8403(6) 0.0455(17) Uani 1 1 d . U . . .
C15 C 0.7713(17) 0.723(2) 0.9497(9) 0.053(7) Uani 0.5 1 d . U P B 1
C16 C 0.6391(17) 0.811(2) 1.0044(11) 0.098(9) Uani 0.5 1 d G . P B 1
H16 H 0.571274 0.866874 0.972096 0.117 Uiso 0.5 1 calc R . P B 1
C17 C 0.6082(19) 0.816(2) 1.1074(10) 0.114(11) Uani 0.5 1 d G . P B 1
H17 H 0.519724 0.874888 1.144039 0.137 Uiso 0.5 1 calc R . P B 1
C18 C 0.710(2) 0.733(3) 1.1557(9) 0.082(10) Uani 0.5 1 d G . P B 1
H18 H 0.688873 0.736007 1.224657 0.098 Uiso 0.5 1 calc R . P B 1
C19 C 0.842(2) 0.645(2) 1.1010(15) 0.108(13) Uani 0.5 1 d G . P B 1
H19 H 0.909574 0.589111 1.133332 0.130 Uiso 0.5 1 calc R . P B 1
C20 C 0.8727(15) 0.640(2) 0.9980(14) 0.090(10) Uani 0.5 1 d G . P B 1
H20 H 0.961127 0.581095 0.961389 0.108 Uiso 0.5 1 calc R . P B 1
C15A C 0.7752(18) 0.7463(14) 0.9516(7) 0.039(7) Uani 0.5 1 d . . P B 2
C16A C 0.7227(17) 0.8755(12) 1.0007(9) 0.065(5) Uani 0.5 1 d G . P B 2
H16A H 0.704694 0.952226 0.964654 0.078 Uiso 0.5 1 calc R . P B 2
C17A C 0.6970(19) 0.8900(14) 1.1035(9) 0.080(6) Uani 0.5 1 d G . P B 2
H17A H 0.661856 0.976451 1.136295 0.096 Uiso 0.5 1 calc R . P B 2
C18A C 0.724(2) 0.7753(19) 1.1573(7) 0.073(9) Uani 0.5 1 d G . P B 2
H18A H 0.706728 0.785035 1.226095 0.088 Uiso 0.5 1 calc R . P B 2
C19A C 0.776(2) 0.6461(15) 1.1083(12) 0.064(7) Uani 0.5 1 d G . P B 2
H19A H 0.794437 0.569393 1.144255 0.076 Uiso 0.5 1 calc R . P B 2
C20A C 0.8021(16) 0.6316(12) 1.0054(12) 0.047(4) Uani 0.5 1 d G . P B 2
H20A H 0.837275 0.545166 0.972614 0.056 Uiso 0.5 1 calc R . P B 2
C21 C 0.3832(7) 0.5969(7) 0.4769(5) 0.0401(16) Uani 1 1 d . . . . .
C22 C 0.5230(8) 0.6015(8) 0.4439(5) 0.0445(17) Uani 1 1 d . . . . .
C23 C 0.6431(7) 0.5022(7) 0.4660(5) 0.0328(14) Uani 1 1 d . . . . .
C24 C 0.7915(7) 0.5061(7) 0.4296(5) 0.0353(15) Uani 1 1 d . . . . .
C25 C 1.120(4) 0.151(2) 0.6283(16) 0.28(2) Uani 1 1 d D U . . .
H25A H 1.165198 0.075761 0.578875 0.422 Uiso 1 1 calc R . . . .
H25B H 1.191956 0.164567 0.658926 0.422 Uiso 1 1 calc R . . . .
H25C H 1.047493 0.132120 0.677719 0.422 Uiso 1 1 calc R . . . .
Er1 Er 0.92064(3) 0.49857(3) 0.64718(2) 0.03313(13) Uani 1 1 d D . . . .
C1 C 0.770(2) 0.2541(17) 0.8937(9) 0.106(5) Uani 1 1 d . . . . .
F1 F 0.6434(16) 0.2436(16) 0.9494(9) 0.207(6) Uani 1 1 d . . . . .
F3 F 0.844(4) 0.1324(17) 0.8523(16) 0.386(19) Uani 1 1 d . . . . .
F2 F 0.872(2) 0.250(2) 0.9378(13) 0.247(9) Uani 1 1 d . . . . .
F7 F 0.2728(5) 0.6973(5) 0.4543(4) 0.0660(14) Uani 1 1 d . . . . .
F8 F 0.5373(5) 0.7056(6) 0.3918(5) 0.0733(16) Uani 1 1 d . . . . .
O1 O 0.8833(6) 0.6067(6) 0.7993(4) 0.0458(12) Uani 1 1 d . . . . .
O2 O 0.8625(6) 0.7278(5) 0.6231(4) 0.0508(13) Uani 1 1 d . . . . .
O3 O 0.6768(6) 0.5738(7) 0.6855(4) 0.0574(15) Uani 1 1 d . . . . .
O4 O 0.8582(7) 0.3563(6) 0.7569(4) 0.0616(16) Uani 1 1 d . . . . .
O5 O 1.0513(6) 0.2749(6) 0.5813(4) 0.0537(13) Uani 1 1 d D U . . .
O6 O 0.8742(5) 0.4886(5) 0.4901(3) 0.0364(10) Uani 1 1 d . . . . .
O7 O 0.8341(5) 0.5251(6) 0.3411(3) 0.0467(12) Uani 1 1 d . . . . .
F6 F 0.6556(18) 1.0648(10) 0.6976(7) 0.258(10) Uani 1 1 d . . . . .
F5 F 0.833(2) 0.9890(9) 0.5772(9) 0.213(8) Uani 1 1 d . . . . .
F4 F 0.6497(17) 0.9461(14) 0.5764(10) 0.214(7) Uani 1 1 d . . . . .
C11 C 0.726(3) 0.9608(14) 0.6381(9) 0.151(9) Uani 1 1 d . . . . .
H5 H 1.022(8) 0.246(3) 0.535(5) 0.227 Uiso 1 1 d DR . . . .


_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
C2 C3 1.367(16) . ?
C2 C1 1.556(17) . ?
C2 O4 1.243(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.418(16) . ?
C4 C5 1.400(13) . ?
C4 C5A 1.68(2) . ?
C4 O3 1.263(10) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C9 1.3900 . ?
C9 H9 0.9300 . ?
C9 C10 1.3900 . ?
C10 H10 0.9300 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A H6A 0.9300 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C10A H10A 0.9300 . ?
C12 C13 1.364(13) . ?
C12 O2 1.284(10) . ?
C12 C11 1.499(15) . ?
C13 H13 0.9300 . ?
C13 C14 1.426(12) . ?
C14 C15 1.478(14) . ?
C14 C15A 1.511(12) . ?
C14 O1 1.233(9) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C16A H16A 0.9300 . ?
C16A C17A 1.3900 . ?
C17A H17A 0.9300 . ?
C17A C18A 1.3900 . ?
C18A H18A 0.9300 . ?
C18A C19A 1.3900 . ?
C19A H19A 0.9300 . ?
C19A C20A 1.3900 . ?
C20A H20A 0.9300 . ?
C21 C22 1.398(10) . ?
C21 C23 1.364(10) 2_666 ?
C21 F7 1.339(8) . ?
C22 C23 1.392(10) . ?
C22 F8 1.336(9) . ?
C23 C24 1.483(9) . ?
C24 Er1 2.843(7) 2_766 ?
C24 O6 1.272(8) . ?
C24 O7 1.247(8) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C25 O5 1.47(2) . ?
Er1 O1 2.286(5) . ?
Er1 O2 2.310(5) . ?
Er1 O3 2.246(5) . ?
Er1 O4 2.266(5) . ?
Er1 O5 2.334(6) . ?
Er1 O6 2.328(4) . ?
Er1 O6 2.528(4) 2_766 ?
Er1 O7 2.432(5) 2_766 ?
C1 F1 1.379(17) . ?
C1 F3 1.30(2) . ?
C1 F2 1.28(2) . ?
O5 H5 0.859(10) . ?
F6 C11 1.262(14) . ?
F5 C11 1.33(3) . ?
F4 C11 1.30(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C1 120.1(10) . . ?
O4 C2 C3 127.6(10) . . ?
O4 C2 C1 112.2(11) . . ?
C2 C3 H3 119.3 . . ?
C2 C3 C4 121.5(8) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 C5A 132.5(11) . . ?
C5 C4 C3 114.1(9) . . ?
O3 C4 C3 124.5(9) . . ?
O3 C4 C5 121.4(11) . . ?
O3 C4 C5A 103.0(12) . . ?
C6 C5 C4 114.7(9) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 125.0(9) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C5 C10 H10 120.0 . . ?
C9 C10 C5 120.0 . . ?
C9 C10 H10 120.0 . . ?
C6A C5A C4 126.5(14) . . ?
C6A C5A C10A 120.0 . . ?
C10A C5A C4 113.5(14) . . ?
C5A C6A H6A 120.0 . . ?
C5A C6A C7A 120.0 . . ?
C7A C6A H6A 120.0 . . ?
C6A C7A C8A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
C5A C10A H10A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C13 C12 C11 117.4(9) . . ?
O2 C12 C13 128.1(9) . . ?
O2 C12 C11 114.4(8) . . ?
C12 C13 H13 118.4 . . ?
C12 C13 C14 123.2(8) . . ?
C14 C13 H13 118.4 . . ?
C13 C14 C15 123.7(10) . . ?
C13 C14 C15A 116.5(9) . . ?
O1 C14 C13 122.5(7) . . ?
O1 C14 C15 113.6(10) . . ?
O1 C14 C15A 120.9(9) . . ?
C16 C15 C14 120.6(11) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C14 119.4(11) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
C16A C15A C14 123.8(10) . . ?
C16A C15A C20A 120.0 . . ?
C20A C15A C14 116.2(10) . . ?
C15A C16A H16A 120.0 . . ?
C17A C16A C15A 120.0 . . ?
C17A C16A H16A 120.0 . . ?
C16A C17A H17A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C18A C17A H17A 120.0 . . ?
C17A C18A H18A 120.0 . . ?
C17A C18A C19A 120.0 . . ?
C19A C18A H18A 120.0 . . ?
C18A C19A H19A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C20A C19A H19A 120.0 . . ?
C15A C20A H20A 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C19A C20A H20A 120.0 . . ?
C23 C21 C22 122.1(6) 2_666 . ?
F7 C21 C22 117.7(7) . . ?
F7 C21 C23 120.2(6) . 2_666 ?
C23 C22 C21 121.1(7) . . ?
F8 C22 C21 117.8(7) . . ?
F8 C22 C23 121.1(6) . . ?
C21 C23 C22 116.8(6) 2_666 . ?
C21 C23 C24 122.2(6) 2_666 . ?
C22 C23 C24 121.0(6) . . ?
C23 C24 Er1 177.0(5) . 2_766 ?
O6 C24 C23 118.7(6) . . ?
O6 C24 Er1 62.8(3) . 2_766 ?
O7 C24 C23 120.3(6) . . ?
O7 C24 Er1 58.3(3) . 2_766 ?
O7 C24 O6 121.0(6) . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
O5 C25 H25A 109.5 . . ?
O5 C25 H25B 109.5 . . ?
O5 C25 H25C 109.5 . . ?
O1 Er1 C24 97.85(19) . 2_766 ?
O1 Er1 O2 73.86(19) . . ?
O1 Er1 O5 132.4(2) . . ?
O1 Er1 O6 118.71(17) . 2_766 ?
O1 Er1 O6 152.45(19) . . ?
O1 Er1 O7 77.55(17) . 2_766 ?
O2 Er1 C24 82.8(2) . 2_766 ?
O2 Er1 O5 147.15(19) . . ?
O2 Er1 O6 75.34(17) . 2_766 ?
O2 Er1 O6 82.60(18) . . ?
O2 Er1 O7 92.5(2) . 2_766 ?
O3 Er1 C24 159.8(2) . 2_766 ?
O3 Er1 O1 81.59(19) . . ?
O3 Er1 O2 77.6(2) . . ?
O3 Er1 O4 74.4(2) . . ?
O3 Er1 O5 120.2(2) . . ?
O3 Er1 O6 139.04(18) . 2_766 ?
O3 Er1 O6 79.52(17) . . ?
O3 Er1 O7 158.7(2) . 2_766 ?
O4 Er1 C24 125.2(2) . 2_766 ?
O4 Er1 O1 75.5(2) . . ?
O4 Er1 O2 140.91(19) . . ?
O4 Er1 O5 71.8(2) . . ?
O4 Er1 O6 117.8(2) . . ?
O4 Er1 O6 142.04(19) . 2_766 ?
O4 Er1 O7 104.0(2) . 2_766 ?
O5 Er1 C24 75.0(2) . 2_766 ?
O5 Er1 O6 73.99(18) . 2_766 ?
O5 Er1 O7 78.00(19) . 2_766 ?
O6 Er1 C24 93.12(17) . 2_766 ?
O6 Er1 C24 26.57(17) 2_766 2_766 ?
O6 Er1 O5 74.86(19) . . ?
O6 Er1 O6 67.04(17) . 2_766 ?
O6 Er1 O7 118.26(15) . 2_766 ?
O7 Er1 C24 25.88(18) 2_766 2_766 ?
O7 Er1 O6 52.44(15) 2_766 2_766 ?
F1 C1 C2 113.4(15) . . ?
F3 C1 C2 113.3(13) . . ?
F3 C1 F1 104.5(16) . . ?
F2 C1 C2 113.8(11) . . ?
F2 C1 F1 118.4(13) . . ?
F2 C1 F3 91(2) . . ?
C14 O1 Er1 135.1(5) . . ?
C12 O2 Er1 128.9(5) . . ?
C4 O3 Er1 135.0(7) . . ?
C2 O4 Er1 133.4(7) . . ?
C25 O5 Er1 131.5(10) . . ?
C25 O5 H5 104(2) . . ?
Er1 O5 H5 116(2) . . ?
C24 O6 Er1 153.8(4) . . ?
C24 O6 Er1 90.7(4) . 2_766 ?
Er1 O6 Er1 112.96(17) . 2_766 ?
C24 O7 Er1 95.8(4) . 2_766 ?
F6 C11 C12 115.6(10) . . ?
F6 C11 F5 106.9(19) . . ?
F6 C11 F4 110.8(19) . . ?
F5 C11 C12 110.0(17) . . ?
F4 C11 C12 111.4(18) . . ?
F4 C11 F5 101.1(12) . . ?

_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_7-dy
_database_code_depnum_ccdc_archive 'CCDC 1569943'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H16 Dy F8 O7'
_chemical_formula_sum            'C25 H16 Dy F8 O7'
_chemical_formula_weight         742.88
_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 0.0033 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'
Dy Dy -0.1892 4.4098 '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'
O O 0.0106 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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.032(5)
_cell_length_b                   10.305(5)
_cell_length_c                   13.828(5)
_cell_angle_alpha                90.672(5)
_cell_angle_beta                 101.907(5)
_cell_angle_gamma                108.705(5)
_cell_volume                     1320.2(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3918
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.7391
_cell_measurement_theta_min      3.3128
_shelx_estimated_absorpt_T_max   0.668
_shelx_estimated_absorpt_T_min   0.651
_exptl_absorpt_coefficient_mu    2.929
_exptl_absorpt_correction_T_max  0.644
_exptl_absorpt_correction_T_min  0.632
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.869
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0833
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8607
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3998
_reflns_number_total             4638
_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       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         1.753
_refine_diff_density_min         -1.403
_refine_diff_density_rms         0.170
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         4638
_refine_ls_number_restraints     539
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0529
_refine_ls_restrained_S_all      1.059
_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)+(0.0746P)²+0.2672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1313
_refine_ls_wR_factor_ref         0.1416
_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, All F(H) groups
2. Restrained distances
 C11-F4
 1.392 with sigma of 0.02
 C11-F5
 1.392 with sigma of 0.02
 C11-F3
 1.392 with sigma of 0.02
 C1-F6
 1.392 with sigma of 0.02
 C1-F7
 1.392 with sigma of 0.02
 C1-F8
 1.392 with sigma of 0.02
 O5-H5
 0.85 with sigma of 0.01
 F4-F5
 2.273 with sigma of 0.04
 F5-F3
 2.273 with sigma of 0.04
 F3-F4
 2.273 with sigma of 0.04
 F6-F7
 2.273 with sigma of 0.04
 F7-F8
 2.273 with sigma of 0.04
 F6-F8
 2.273 with sigma of 0.04
 C25-H5
 1.847385 with sigma of 0.02
 Dy1-H5
 2.873345 with sigma of 0.02
3. Rigid bond restraints
 C5A, C6A, C7A, C8A, C9A, C10A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15A, C16A, C17A, C18A, C19A, C20A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C15, C16, C17, C18, C19, C20
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11, F3, F4, F5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C11A, F3A, F4A, F5A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 O5, C25
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 F6, C1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, O5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5A \\sim C6A \\sim C7A \\sim C8A \\sim C9A \\sim C10A: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C5 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 3.8A with sigma of
0.04 and sigma for terminal atoms of 0.08
C15A \\sim C16A \\sim C17A \\sim C18A \\sim C19A \\sim C20A: within 3.8A with
sigma of 0.04 and sigma for terminal atoms of 0.08
C15 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within 3.8A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C11 \\sim F3 \\sim F4 \\sim F5: within 3.8A with sigma of 0.04 and sigma for
terminal atoms of 0.08
C11A \\sim F3A \\sim F4A \\sim F5A: within 3.8A with sigma of 0.04 and sigma
for terminal atoms of 0.08
C25 \\sim O5: within 3.8A with sigma of 0.04 and sigma for terminal atoms of
0.08
Uanis(C5) \\sim Ueq, Uanis(C11) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(O5) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5) H8(0.5) C9(0.5)
 H9(0.5) C10(0.5) H10(0.5) C5A(0.5) C6A(0.5) H6A(0.5) C7A(0.5) H7A(0.5)
 C8A(0.5) H8A(0.5) C9A(0.5) H9A(0.5) C10A(0.5) H10A(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5) C20(0.5)
 H20(0.5) C15A(0.5) C16A(0.5) H16A(0.5) C17A(0.5) H17A(0.5) C18A(0.5) H18A(0.5)
 C19A(0.5) H19A(0.5) C20A(0.5) H20A(0.5) C11(0.5) F3(0.5) F4(0.5) F5(0.5)
 C11A(0.5) F3A(0.5) F4A(0.5) F5A(0.5)
6.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C)
6.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C6A(H6A), C7A(H7A),
 C8A(H8A), C9A(H9A), C10A(H10A), C13(H13), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A), C20A(H20A)
6.c Fitted hexagon refined as free rotating group:
 C5(C6,C7,C8,C9,C10), C5A(C6A,C7A,C8A,C9A,C10A), C15(C16,C17,C18,C19,C20),
 C15A(C16A,C17A,C18A,C19A,C20A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C2 C 0.2596(13) 0.3656(14) 0.8178(8) 0.071(3) Uani 1 1 d . . . . .
C3 C 0.3914(14) 0.4590(16) 0.8244(9) 0.084(4) Uani 1 1 d . . . . .
H3 H 0.466341 0.457194 0.876123 0.100 Uiso 1 1 calc R . . . .
C4 C 0.4204(10) 0.5598(14) 0.7557(8) 0.070(4) Uani 1 1 d . . . . .
C5 C 0.5681(19) 0.679(3) 0.745(2) 0.094(8) Uani 0.5 1 d . U P A 1
C6 C 0.573(2) 0.784(3) 0.682(2) 0.115(9) Uani 0.5 1 d G U P A 1
H6 H 0.487974 0.794260 0.646995 0.139 Uiso 0.5 1 calc R . P A 1
C7 C 0.706(3) 0.875(3) 0.673(2) 0.138(10) Uani 0.5 1 d G U P A 1
H7 H 0.708936 0.945764 0.631441 0.165 Uiso 0.5 1 calc R . P A 1
C8 C 0.833(2) 0.860(3) 0.726(2) 0.132(9) Uani 0.5 1 d G U P A 1
H8 H 0.921417 0.921013 0.719771 0.158 Uiso 0.5 1 calc R . P A 1
C9 C 0.8278(19) 0.755(3) 0.788(2) 0.135(9) Uani 0.5 1 d G U P A 1
H9 H 0.912938 0.744757 0.823656 0.162 Uiso 0.5 1 calc R . P A 1
C10 C 0.695(2) 0.664(3) 0.798(2) 0.106(8) Uani 0.5 1 d G U P A 1
H10 H 0.691976 0.593251 0.839211 0.128 Uiso 0.5 1 calc R . P A 1
C5A C 0.5667(12) 0.636(2) 0.7664(13) 0.052(5) Uani 0.5 1 d . U P A 2
C6A C 0.5946(15) 0.733(2) 0.6980(15) 0.076(7) Uani 0.5 1 d G U P A 2
H6A H 0.518804 0.743408 0.650680 0.091 Uiso 0.5 1 calc R . P A 2
C7A C 0.7356(17) 0.815(2) 0.7004(16) 0.106(8) Uani 0.5 1 d G U P A 2
H7A H 0.754234 0.880479 0.654573 0.128 Uiso 0.5 1 calc R . P A 2
C8A C 0.8489(13) 0.800(2) 0.7711(17) 0.109(9) Uani 0.5 1 d G U P A 2
H8A H 0.943227 0.854984 0.772666 0.130 Uiso 0.5 1 calc R . P A 2
C9A C 0.8210(14) 0.703(2) 0.8395(16) 0.104(8) Uani 0.5 1 d G U P A 2
H9A H 0.896790 0.692418 0.886868 0.125 Uiso 0.5 1 calc R . P A 2
C10A C 0.6800(16) 0.621(2) 0.8372(13) 0.078(7) Uani 0.5 1 d G U P A 2
H10A H 0.661360 0.555346 0.882977 0.093 Uiso 0.5 1 calc R . P A 2
C12 C 0.2115(11) 0.8343(11) 0.6870(7) 0.060(3) Uani 1 1 d . . . . .
C13 C 0.2473(11) 0.8390(11) 0.7863(7) 0.061(3) Uani 1 1 d . . . . .
H13 H 0.311136 0.920727 0.820775 0.074 Uiso 1 1 calc R . . . .
C14 C 0.1930(8) 0.7255(10) 0.8422(6) 0.0408(19) Uani 1 1 d . . . . .
C15 C 0.2228(14) 0.7524(15) 0.9536(7) 0.031(4) Uani 0.5 1 d . U P B 1
C16 C 0.2787(15) 0.8839(13) 1.0019(9) 0.049(4) Uani 0.5 1 d G U P B 1
H16 H 0.298591 0.960267 0.965385 0.058 Uiso 0.5 1 calc R . P B 1
C17 C 0.3049(15) 0.9011(13) 1.1047(9) 0.060(4) Uani 0.5 1 d G U P B 1
H17 H 0.342289 0.989063 1.136997 0.072 Uiso 0.5 1 calc R . P B 1
C18 C 0.2752(16) 0.7869(17) 1.1593(7) 0.055(5) Uani 0.5 1 d G U P B 1
H18 H 0.292706 0.798437 1.228077 0.066 Uiso 0.5 1 calc R . P B 1
C19 C 0.2193(16) 0.6554(14) 1.1110(10) 0.057(5) Uani 0.5 1 d G U P B 1
H19 H 0.199423 0.579014 1.147546 0.068 Uiso 0.5 1 calc R . P B 1
C20 C 0.1931(15) 0.6382(13) 1.0082(10) 0.045(4) Uani 0.5 1 d G U P B 1
H20 H 0.155723 0.550214 0.975934 0.054 Uiso 0.5 1 calc R . P B 1
C15A C 0.226(2) 0.728(2) 0.9505(10) 0.063(7) Uani 0.5 1 d . U P B 2
C16A C 0.348(2) 0.827(2) 1.0067(13) 0.120(9) Uani 0.5 1 d G U P B 2
H16A H 0.411195 0.890130 0.975479 0.144 Uiso 0.5 1 calc R . P B 2
C17A C 0.377(2) 0.831(2) 1.1097(12) 0.126(9) Uani 0.5 1 d G U P B 2
H17A H 0.458762 0.896861 1.147264 0.151 Uiso 0.5 1 calc R . P B 2
C18A C 0.283(2) 0.737(3) 1.1564(10) 0.090(8) Uani 0.5 1 d G U P B 2
H18A H 0.301821 0.739204 1.225251 0.109 Uiso 0.5 1 calc R . P B 2
C19A C 0.160(2) 0.638(2) 1.1002(15) 0.100(9) Uani 0.5 1 d G U P B 2
H19A H 0.097313 0.574817 1.131454 0.120 Uiso 0.5 1 calc R . P B 2
C20A C 0.1317(19) 0.634(2) 0.9973(15) 0.094(9) Uani 0.5 1 d G U P B 2
H20A H 0.049744 0.568085 0.959670 0.113 Uiso 0.5 1 calc R . P B 2
C24 C 0.6159(7) 0.5959(9) 0.4783(6) 0.0386(19) Uani 1 1 d . . . . .
C22 C 0.4786(8) 0.6031(10) 0.4440(6) 0.042(2) Uani 1 1 d . . . . .
C23 C 0.3580(7) 0.5029(9) 0.4651(5) 0.0341(17) Uani 1 1 d . . . . .
C21 C 0.2096(7) 0.5059(9) 0.4282(6) 0.0357(18) Uani 1 1 d . . . . .
C25 C -0.104(3) 0.153(3) 0.626(2) 0.28(2) Uani 1 1 d D U . . .
H25A H -0.148580 0.075952 0.577235 0.420 Uiso 1 1 calc R . . . .
H25B H -0.029069 0.136761 0.674020 0.420 Uiso 1 1 calc R . . . .
H25C H -0.175368 0.166783 0.658041 0.420 Uiso 1 1 calc R . . . .
Dy1 Dy 0.07971(3) 0.49848(4) 0.64771(2) 0.03166(17) Uani 1 1 d D . . . .
F1 F 0.4608(5) 0.7074(7) 0.3911(5) 0.0678(17) Uani 1 1 d . . . . .
F2 F 0.7258(5) 0.6967(6) 0.4557(4) 0.0603(15) Uani 1 1 d . . . . .
C11 C 0.299(3) 0.944(3) 0.633(2) 0.102(9) Uani 0.5 1 d D U P C 1
F3 F 0.362(3) 0.915(3) 0.5599(18) 0.154(10) Uani 0.5 1 d D U P C 1
F4 F 0.200(3) 1.003(3) 0.587(3) 0.152(10) Uani 0.5 1 d D U P C 1
F5 F 0.411(3) 1.039(2) 0.6951(15) 0.153(8) Uani 0.5 1 d D U P C 1
C11A C 0.250(3) 0.977(2) 0.6402(16) 0.056(4) Uani 0.5 1 d . U P C 2
F3A F 0.332(3) 0.968(2) 0.5850(19) 0.110(7) Uani 0.5 1 d . U P C 2
F4A F 0.126(2) 0.992(3) 0.5812(19) 0.121(8) Uani 0.5 1 d . U P C 2
F5A F 0.3156(18) 1.0778(13) 0.7013(10) 0.078(4) Uani 0.5 1 d . U P C 2
O2 O 0.1345(6) 0.7301(6) 0.6243(4) 0.0484(15) Uani 1 1 d . . . . .
O1 O 0.1163(6) 0.6100(7) 0.8014(4) 0.0456(15) Uani 1 1 d . . . . .
O3 O 0.3239(6) 0.5751(8) 0.6858(4) 0.0579(18) Uani 1 1 d . . . . .
O4 O 0.1462(7) 0.3552(8) 0.7575(5) 0.0621(18) Uani 1 1 d . . . . .
O6 O 0.1268(5) 0.4896(6) 0.4885(3) 0.0343(12) Uani 1 1 d . . . . .
O7 O 0.1679(5) 0.5259(7) 0.3404(4) 0.0436(15) Uani 1 1 d . . . . .
O5 O -0.0459(6) 0.2699(6) 0.5794(4) 0.0484(14) Uani 1 1 d D U . . .
C1 C 0.2355(15) 0.2579(15) 0.8991(10) 0.101(4) Uani 1 1 d D U . . .
F7 F 0.3655(14) 0.2541(18) 0.9516(9) 0.219(7) Uani 1 1 d D . . . .
F6 F 0.136(2) 0.269(2) 0.9490(12) 0.248(10) Uani 1 1 d D U . . .
F8 F 0.161(3) 0.1340(14) 0.8540(13) 0.323(15) Uani 1 1 d D . . . .
H5 H -0.026(12) 0.244(4) 0.527(5) 0.485 Uiso 1 1 d DR . . . .


_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
C2 C3 1.347(17) . ?
C2 O4 1.236(12) . ?
C2 C1 1.589(18) . ?
C3 C4 1.418(18) . ?
C4 C5 1.63(2) . ?
C4 C5A 1.400(15) . ?
C4 O3 1.270(13) . ?
C5 C6 1.3900 . ?
C5 C10 1.3900 . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C9 C10 1.3900 . ?
C5A C6A 1.3900 . ?
C5A C10A 1.3900 . ?
C6A C7A 1.3900 . ?
C7A C8A 1.3900 . ?
C8A C9A 1.3900 . ?
C9A C10A 1.3900 . ?
C12 C13 1.342(13) . ?
C12 C11 1.51(3) . ?
C12 C11A 1.58(2) . ?
C12 O2 1.292(12) . ?
C13 C14 1.432(13) . ?
C14 C15 1.512(12) . ?
C14 C15A 1.463(16) . ?
C14 O1 1.244(10) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
C15A C16A 1.3900 . ?
C15A C20A 1.3900 . ?
C16A C17A 1.3900 . ?
C17A C18A 1.3900 . ?
C18A C19A 1.3900 . ?
C19A C20A 1.3900 . ?
C24 C22 1.387(11) . ?
C24 C23 1.350(11) 2_666 ?
C24 F2 1.344(8) . ?
C22 C23 1.402(11) . ?
C22 F1 1.345(10) . ?
C23 C21 1.481(10) . ?
C21 Dy1 2.861(7) 2_566 ?
C21 O6 1.270(8) . ?
C21 O7 1.243(9) . ?
C25 O5 1.38(2) . ?
Dy1 O2 2.314(6) . ?
Dy1 O1 2.306(6) . ?
Dy1 O3 2.262(5) . ?
Dy1 O4 2.280(6) . ?
Dy1 O6 2.532(5) 2_566 ?
Dy1 O6 2.352(5) . ?
Dy1 O7 2.456(5) 2_566 ?
Dy1 O5 2.362(6) . ?
C11 F3 1.371(19) . ?
C11 F4 1.378(19) . ?
C11 F5 1.355(19) . ?
C11A F3A 1.25(3) . ?
C11A F4A 1.40(3) . ?
C11A F5A 1.24(2) . ?
C1 F7 1.368(13) . ?
C1 F6 1.358(15) . ?
C1 F8 1.324(15) . ?

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
C3 C2 C1 119.5(10) . . ?
O4 C2 C3 128.2(12) . . ?
O4 C2 C1 112.2(11) . . ?
C2 C3 C4 122.7(10) . . ?
C3 C4 C5 132.4(13) . . ?
C5A C4 C3 114.5(12) . . ?
O3 C4 C3 123.4(10) . . ?
O3 C4 C5 104.2(13) . . ?
O3 C4 C5A 122.0(13) . . ?
C6 C5 C4 124.5(14) . . ?
C6 C5 C10 120.0 . . ?
C10 C5 C4 115.3(14) . . ?
C7 C6 C5 120.0 . . ?
C8 C7 C6 120.0 . . ?
C9 C8 C7 120.0 . . ?
C10 C9 C8 120.0 . . ?
C9 C10 C5 120.0 . . ?
C6A C5A C4 114.2(11) . . ?
C6A C5A C10A 120.0 . . ?
C10A C5A C4 125.8(11) . . ?
C5A C6A C7A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C9A C8A C7A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
C9A C10A C5A 120.0 . . ?
C13 C12 C11 120.0(12) . . ?
C13 C12 C11A 116.3(12) . . ?
O2 C12 C13 128.7(10) . . ?
O2 C12 C11 108.7(12) . . ?
O2 C12 C11A 114.5(11) . . ?
C12 C13 C14 123.8(9) . . ?
C13 C14 C15 117.8(9) . . ?
C13 C14 C15A 125.2(11) . . ?
O1 C14 C13 121.9(7) . . ?
O1 C14 C15 120.2(9) . . ?
O1 C14 C15A 112.8(11) . . ?
C16 C15 C14 123.0(9) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C14 117.0(10) . . ?
C17 C16 C15 120.0 . . ?
C16 C17 C18 120.0 . . ?
C19 C18 C17 120.0 . . ?
C18 C19 C20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C16A C15A C14 120.4(13) . . ?
C16A C15A C20A 120.0 . . ?
C20A C15A C14 119.6(13) . . ?
C17A C16A C15A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C19A C18A C17A 120.0 . . ?
C20A C19A C18A 120.0 . . ?
C19A C20A C15A 120.0 . . ?
C23 C24 C22 123.1(7) 2_666 . ?
F2 C24 C22 116.6(8) . . ?
F2 C24 C23 120.3(7) . 2_666 ?
C24 C22 C23 120.3(7) . . ?
F1 C22 C24 120.0(7) . . ?
F1 C22 C23 119.7(7) . . ?
C24 C23 C22 116.6(7) 2_666 . ?
C24 C23 C21 121.6(7) 2_666 . ?
C22 C23 C21 121.8(7) . . ?
C23 C21 Dy1 177.7(6) . 2_566 ?
O6 C21 C23 118.6(7) . . ?
O6 C21 Dy1 62.2(4) . 2_566 ?
O7 C21 C23 120.6(6) . . ?
O7 C21 Dy1 58.7(4) . 2_566 ?
O7 C21 O6 120.8(6) . . ?
O2 Dy1 C21 82.9(2) . 2_566 ?
O2 Dy1 O6 75.60(19) . 2_566 ?
O2 Dy1 O6 82.1(2) . . ?
O2 Dy1 O7 92.6(2) . 2_566 ?
O2 Dy1 O5 147.1(2) . . ?
O1 Dy1 C21 97.9(2) . 2_566 ?
O1 Dy1 O2 73.6(2) . . ?
O1 Dy1 O6 151.8(2) . . ?
O1 Dy1 O6 118.65(19) . 2_566 ?
O1 Dy1 O7 78.03(19) . 2_566 ?
O1 Dy1 O5 133.3(2) . . ?
O3 Dy1 C21 159.7(3) . 2_566 ?
O3 Dy1 O2 77.4(2) . . ?
O3 Dy1 O1 81.3(2) . . ?
O3 Dy1 O4 74.1(3) . . ?
O3 Dy1 O6 79.61(19) . . ?
O3 Dy1 O6 139.36(19) . 2_566 ?
O3 Dy1 O7 158.9(2) . 2_566 ?
O3 Dy1 O5 119.6(2) . . ?
O4 Dy1 C21 125.6(2) . 2_566 ?
O4 Dy1 O2 140.6(2) . . ?
O4 Dy1 O1 75.5(2) . . ?
O4 Dy1 O6 142.1(2) . 2_566 ?
O4 Dy1 O6 118.2(2) . . ?
O4 Dy1 O7 104.4(2) . 2_566 ?
O4 Dy1 O5 72.1(2) . . ?
O6 Dy1 C21 93.00(19) . 2_566 ?
O6 Dy1 C21 26.34(18) 2_566 2_566 ?
O6 Dy1 O6 67.06(18) . 2_566 ?
O6 Dy1 O7 117.86(16) . 2_566 ?
O6 Dy1 O5 74.6(2) . . ?
O7 Dy1 C21 25.61(18) 2_566 2_566 ?
O7 Dy1 O6 51.93(16) 2_566 2_566 ?
O5 Dy1 C21 75.6(2) . 2_566 ?
O5 Dy1 O6 74.09(19) . 2_566 ?
O5 Dy1 O7 78.6(2) . 2_566 ?
F3 C11 C12 123(2) . . ?
F3 C11 F4 106(3) . . ?
F4 C11 C12 103(2) . . ?
F5 C11 C12 113(2) . . ?
F5 C11 F3 103(2) . . ?
F5 C11 F4 110(2) . . ?
F3A C11A C12 104(2) . . ?
F3A C11A F4A 108(2) . . ?
F4A C11A C12 110.0(18) . . ?
F5A C11A C12 114.5(17) . . ?
F5A C11A F3A 108(2) . . ?
F5A C11A F4A 111(2) . . ?
C12 O2 Dy1 128.4(6) . . ?
C14 O1 Dy1 134.5(5) . . ?
C4 O3 Dy1 135.0(7) . . ?
C2 O4 Dy1 133.0(8) . . ?
C21 O6 Dy1 153.5(5) . . ?
C21 O6 Dy1 91.4(4) . 2_566 ?
Dy1 O6 Dy1 112.94(18) . 2_566 ?
C21 O7 Dy1 95.7(4) . 2_566 ?
C25 O5 Dy1 129.7(14) . . ?
F7 C1 C2 110.2(12) . . ?
F6 C1 C2 112.1(12) . . ?
F6 C1 F7 119.1(13) . . ?
F8 C1 C2 108.9(12) . . ?
F8 C1 F7 107.9(15) . . ?
F8 C1 F6 97.4(16) . . ?

_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_6-tb
_database_code_depnum_ccdc_archive 'CCDC 1569942'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2018-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C25 H14 F8 O7 Tb'
_chemical_formula_sum            'C25 H14 F8 O7 Tb'
_chemical_formula_weight         739.30
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.061(5)
_cell_length_b                   10.460(5)
_cell_length_c                   13.851(5)
_cell_angle_alpha                90.122(5)
_cell_angle_beta                 101.933(5)
_cell_angle_gamma                109.483(5)
_cell_volume                     1340.5(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.4627
_cell_measurement_theta_min      3.3128
_shelx_estimated_absorpt_T_max   0.584
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    2.736
_exptl_absorpt_correction_T_max  0.548
_exptl_absorpt_correction_T_min  0.510
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.827
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.22
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0329
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8859
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.319
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4206
_reflns_number_total             4706
_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       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         2.006
_refine_diff_density_min         -1.012
_refine_diff_density_rms         0.177
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         4706
_refine_ls_number_restraints     286
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0520
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0844P)²+5.5892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1497
_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) groups, All C(H,H,H) groups
2. Restrained distances
 C1-F4 = C1-F11 = C1-F1 = C1-F12 = C1-F10 = C1-F4
 1.38 with sigma of 0.01
 O5-H5A
 0.85 with sigma of 0.01
 O5-H5B
 0.85 with sigma of 0.01
 C25-H5A
 1.902087 with sigma of 0.02
 Tb01-H5A
 2.955786 with sigma of 0.02
 C25'-H5B
 1.879182 with sigma of 0.02
 Tb01-H5B
 2.927884 with sigma of 0.02
3. Rigid bond restraints
 C1, F12
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, F11
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, F5
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, F6
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, F7
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C1, C2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C13, C14
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C11, F5, F6, F7
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C11 \\sim F5 \\sim F6 \\sim F7: within 3.8A with sigma of 0.04 and sigma for
terminal atoms of 0.08
Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(C18)
\\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(O4) \\sim Ueq,
Uanis(O3) \\sim Ueq, Uanis(O1) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(O5) \\sim
Ueq, Uanis(O6) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6)
\\sim Ueq, Uanis(F7) \\sim Ueq, Uanis(F8) \\sim Ueq, Uanis(F9) \\sim Ueq,
Uanis(F10) \\sim Ueq, Uanis(F11) \\sim Ueq, Uanis(F12) \\sim Ueq, Uanis(Tb01)
\\sim Ueq, Uanis(C6') \\sim Ueq, Uanis(C5') \\sim Ueq, Uanis(C10') \\sim Ueq,
Uanis(C9') \\sim Ueq, Uanis(C8') \\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(F2)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F1) \\sim Ueq, Uanis(C25') \\sim Ueq,
Uanis(C15') \\sim Ueq, Uanis(C16') \\sim Ueq, Uanis(C17') \\sim Ueq,
Uanis(C18') \\sim Ueq, Uanis(C19') \\sim Ueq, Uanis(C20') \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.01
Uanis(C6') = Uanis(C6) = Uanis(C25) = Uanis(C25') = Uanis(C18) = Uanis(C18') =
Uanis(C17') = Uanis(C17) = Uanis(C19) = Uanis(C19')
5. Others
 Fixed Sof: C10(0.5) H10(0.5) C5(0.5) C6(0.5) H6(0.5) C7(0.5) H7(0.5) C8(0.5)
 H8(0.5) C9(0.5) H9(0.5) C25(0.5) H25A(0.5) H25B(0.5) H25C(0.5) C15(0.5)
 C16(0.5) H16(0.5) C17(0.5) H17(0.5) C18(0.5) H18(0.5) C19(0.5) H19(0.5)
 C20(0.5) H20(0.5) F10(0.5) F11(0.5) F12(0.5) C6'(0.5) H6'(0.5) C5'(0.5)
 C10'(0.5) H10'(0.5) C9'(0.5) H9'(0.5) C8'(0.5) H8'(0.5) C7'(0.5) H7'(0.5)
 F2(0.5) F4(0.5) F1(0.5) C25'(0.5) H25D(0.5) H25E(0.5) H25F(0.5) C15'(0.5)
 C16'(0.5) H16'(0.5) C17'(0.5) H17'(0.5) C18'(0.5) H18'(0.5) C19'(0.5)
 H19'(0.5) C20'(0.5) H20'(0.5) H5A(0.5) H5B(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C6(H6), C7(H7), C8(H8), C9(H9), C16(H16), C17(H17), C18(H18),
 C19(H19), C20(H20), C6'(H6'), C10'(H10'), C9'(H9'), C8'(H8'), C7'(H7'),
 C16'(H16'), C17'(H17'), C18'(H18'), C19'(H19'), C20'(H20')
6.b Fitted hexagon refined as free rotating group:
 C10(C5,C6,C7,C8,C9), C15(C16,C17,C18,C19,C20), C6'(C5',C10',C9',C8',C7'),
 C15'(C16',C17',C18',C19',C20')
6.c Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C25'(H25D,H25E,H25F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
C10 C -0.1925(8) 0.3670(8) -0.0050(5) 0.049(4) Uani 0.5 1 d . . P A 1
H10 H -0.154553 0.453487 0.027649 0.058 Uiso 0.5 1 calc R . P A 1
C5 C -0.2225(11) 0.2528(9) 0.0489(5) 0.041(4) Uani 0.5 1 d G . P A 1
C6 C -0.2792(14) 0.1235(8) 0.0000(8) 0.1433(16) Uani 0.5 1 d G . P A 1
H6 H -0.299262 0.047098 0.036090 0.172 Uiso 0.5 1 calc R . P A 1
C7 C -0.3061(14) 0.1085(9) -0.1026(8) 0.071(5) Uani 0.5 1 d G . P A 1
H7 H -0.344028 0.022075 -0.135283 0.085 Uiso 0.5 1 calc R . P A 1
C8 C -0.2761(14) 0.2228(11) -0.1565(5) 0.073(6) Uani 0.5 1 d G . P A 1
H8 H -0.294057 0.212758 -0.225191 0.088 Uiso 0.5 1 calc R . P A 1
C9 C -0.2194(11) 0.3520(10) -0.1077(5) 0.068(5) Uani 0.5 1 d G . P A 1
H9 H -0.199320 0.428464 -0.143727 0.081 Uiso 0.5 1 calc R . P A 1
C1 C -0.2782(6) 0.0375(7) 0.3590(4) 0.1312(10) Uani 1 1 d D U . . .
C2 C -0.2151(10) 0.1677(9) 0.3129(6) 0.071(2) Uani 1 1 d . U . . .
C3 C -0.2508(10) 0.1640(8) 0.2135(6) 0.067(3) Uani 1 1 d . . . . .
C4 C -0.1937(7) 0.2771(7) 0.1578(5) 0.0452(16) Uani 1 1 d . . . . .
C21 C 0.2108(6) 0.5079(6) 0.4288(4) 0.0364(14) Uani 1 1 d . . . . .
C22 C 0.3574(6) 0.5029(6) 0.4650(4) 0.0372(14) Uani 1 1 d . . . . .
C23 C 0.4788(6) 0.6007(6) 0.4435(5) 0.0421(15) Uani 1 1 d . . . . .
C24 C 0.6158(6) 0.5965(6) 0.4771(5) 0.0407(15) Uani 1 1 d . . . . .
C11 C -0.2257(17) 0.7502(12) 0.1034(9) 0.1681(10) Uani 1 1 d . U . . .
C12 C -0.2576(9) 0.6366(9) 0.1810(6) 0.069(2) Uani 1 1 d . . . . .
C13 C -0.3915(10) 0.5436(10) 0.1748(7) 0.0810(19) Uani 1 1 d . U . . .
C14 C -0.4203(8) 0.4443(9) 0.2426(6) 0.0638(15) Uani 1 1 d . U . . .
C25 C 0.013(3) 0.864(2) 0.3844(18) 0.1433(16) Uani 0.5 1 d D . P B 3
H25A H -0.076606 0.837108 0.336120 0.215 Uiso 0.5 1 calc GR . P B 3
H25B H 0.088714 0.922250 0.355668 0.215 Uiso 0.5 1 calc GR . P B 3
H25C H 0.004699 0.912796 0.440426 0.215 Uiso 0.5 1 calc GR . P B 3
C15 C -0.5687(10) 0.3266(10) 0.2449(8) 0.053(3) Uani 0.5 1 d . U P C 1
C16 C -0.5796(15) 0.2221(13) 0.3079(10) 0.083(4) Uani 0.5 1 d G U P C 1
H16 H -0.496358 0.211048 0.344970 0.100 Uiso 0.5 1 calc R . P C 1
C17 C -0.7147(19) 0.1342(15) 0.3156(14) 0.1433(16) Uani 0.5 1 d G U P C 1
H17 H -0.721968 0.064317 0.357732 0.172 Uiso 0.5 1 calc R . P C 1
C18 C -0.8391(14) 0.1508(18) 0.2602(16) 0.1433(16) Uani 0.5 1 d G U P C 1
H18 H -0.929533 0.091999 0.265339 0.172 Uiso 0.5 1 calc R . P C 1
C19 C -0.8283(10) 0.2553(19) 0.1972(14) 0.1433(16) Uani 0.5 1 d G U P C 1
H19 H -0.911489 0.266409 0.160182 0.172 Uiso 0.5 1 calc R . P C 1
C20 C -0.6931(13) 0.3432(14) 0.1896(10) 0.071(3) Uani 0.5 1 d G U P C 1
H20 H -0.685879 0.413141 0.147418 0.085 Uiso 0.5 1 calc R . P C 1
O4 O -0.1391(5) 0.2694(5) 0.3760(3) 0.0534(13) Uani 1 1 d . U . . .
O3 O -0.1174(5) 0.3911(5) 0.1987(3) 0.0467(11) Uani 1 1 d . U . . .
O1 O -0.3249(5) 0.4266(5) 0.3125(4) 0.0567(13) Uani 1 1 d . U . . .
O2 O -0.1437(6) 0.6455(5) 0.2421(4) 0.0587(13) Uani 1 1 d . U . . .
O5 O 0.0517(5) 0.7300(5) 0.4198(3) 0.0537(13) Uani 1 1 d D U . . .
O6 O 0.1693(5) 0.5262(5) 0.3403(3) 0.0475(11) Uani 1 1 d . U . . .
O7 O 0.1269(4) 0.4902(4) 0.4884(3) 0.0390(10) Uani 1 1 d . U . . .
F5 F -0.3564(13) 0.7605(12) 0.0517(9) 0.200(3) Uani 1 1 d . U . . .
F6 F -0.1382(16) 0.7384(15) 0.0510(11) 0.234(2) Uani 1 1 d . U . . .
F7 F -0.1614(17) 0.8670(14) 0.1432(11) 0.231(3) Uani 1 1 d . U . . .
F8 F 0.4637(4) 0.7050(4) 0.3907(4) 0.0700(13) Uani 1 1 d . U . . .
F9 F 0.7273(4) 0.6956(4) 0.4547(4) 0.0669(12) Uani 1 1 d . U . . .
F10 F -0.3242(13) -0.0774(7) 0.2967(7) 0.086(3) Uani 0.5 1 d D U P D 1
F11 F -0.1618(12) -0.0032(16) 0.398(2) 0.253(3) Uani 0.5 1 d D U P D 2
F12 F -0.3696(10) 0.0640(13) 0.4120(8) 0.1385(19) Uani 0.5 1 d D U P D 1
Tb01 Tb -0.07926(3) 0.50267(3) 0.35189(2) 0.03431(8) Uani 1 1 d D U . . .
C6' C -0.3587(12) 0.1885(11) -0.0047(9) 0.1433(16) Uani 0.5 1 d . U P A 2
H6' H -0.426929 0.133951 0.027619 0.172 Uiso 0.5 1 calc R . P A 2
C5' C -0.2266(13) 0.2749(13) 0.0497(9) 0.067(4) Uani 0.5 1 d G U P A 2
C10' C -0.1246(12) 0.3563(14) 0.0013(12) 0.095(4) Uani 0.5 1 d G U P A 2
H10' H -0.036233 0.414150 0.037693 0.114 Uiso 0.5 1 calc R . P A 2
C9' C -0.1546(17) 0.3514(16) -0.1015(13) 0.112(4) Uani 0.5 1 d G U P A 2
H9' H -0.086344 0.405882 -0.133857 0.134 Uiso 0.5 1 calc R . P A 2
C8' C -0.2867(19) 0.2650(18) -0.1559(9) 0.096(4) Uani 0.5 1 d G U P A 2
H8' H -0.306747 0.261649 -0.224671 0.115 Uiso 0.5 1 calc R . P A 2
C7' C -0.3887(14) 0.1835(14) -0.1075(9) 0.113(4) Uani 0.5 1 d G U P A 2
H7' H -0.477041 0.125683 -0.143935 0.136 Uiso 0.5 1 calc R . P A 2
F2 F -0.4207(19) -0.0333(18) 0.3116(13) 0.141(5) Uani 0.5 1 d . U P D 2
F4 F -0.3222(12) 0.0424(15) 0.4452(5) 0.136(5) Uani 0.5 1 d D U P D 2
F1 F -0.1727(11) 0.0089(10) 0.4253(8) 0.111(4) Uani 0.5 1 d D U P D 1
C25' C 0.126(3) 0.842(3) 0.3675(15) 0.1433(16) Uani 0.5 1 d D U P B 4
H25D H 0.145684 0.926191 0.404476 0.215 Uiso 0.5 1 calc GR . P B 4
H25E H 0.066305 0.840207 0.303467 0.215 Uiso 0.5 1 calc GR . P B 4
H25F H 0.215289 0.832798 0.359944 0.215 Uiso 0.5 1 calc GR . P B 4
C15' C -0.5661(10) 0.3761(10) 0.2316(7) 0.067(3) Uani 0.5 1 d . U P C 2
C16' C -0.5987(13) 0.2829(12) 0.3020(8) 0.052(3) Uani 0.5 1 d G U P C 2
H16' H -0.524891 0.273182 0.351013 0.062 Uiso 0.5 1 calc R . P C 2
C17' C -0.7416(15) 0.2044(15) 0.2992(12) 0.1433(16) Uani 0.5 1 d G U P C 2
H17' H -0.763356 0.142012 0.346334 0.172 Uiso 0.5 1 calc R . P C 2
C18' C -0.8519(11) 0.2190(18) 0.2260(15) 0.1433(16) Uani 0.5 1 d G U P C 2
H18' H -0.947480 0.166370 0.224110 0.172 Uiso 0.5 1 calc R . P C 2
C19' C -0.8193(11) 0.3121(18) 0.1556(13) 0.1433(16) Uani 0.5 1 d G U P C 2
H19' H -0.893142 0.321900 0.106565 0.172 Uiso 0.5 1 calc R . P C 2
C20' C -0.6765(13) 0.3907(13) 0.1584(9) 0.069(3) Uani 0.5 1 d G U P C 2
H20' H -0.654676 0.453071 0.111243 0.083 Uiso 0.5 1 calc R . P C 2
H5A H 0.076(5) 0.7559(17) 0.4811(7) 0.104 Uiso 0.5 1 d DR . P E 3
H5B H 0.0281(17) 0.7655(14) 0.4661(9) 0.104 Uiso 0.5 1 d DR . P F 4


_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
C10 C5 1.3900 . ?
C10 C9 1.3900 . ?
C5 C6 1.3900 . ?
C5 C4 1.481(10) . ?
C6 C7 1.3900 . ?
C7 C8 1.3900 . ?
C8 C9 1.3900 . ?
C1 C2 1.504(11) . ?
C1 F10 1.364(8) . ?
C1 F11 1.386(9) . ?
C1 F12 1.381(9) . ?
C1 F2 1.391(17) . ?
C1 F4 1.362(6) . ?
C1 F1 1.367(8) . ?
C2 C3 1.346(11) . ?
C2 O4 1.287(9) . ?
C3 C4 1.435(10) . ?
C4 O3 1.240(8) . ?
C4 C5' 1.464(14) . ?
C21 C22 1.475(8) . ?
C21 O6 1.248(7) . ?
C21 O7 1.269(7) . ?
C21 Tb01 2.874(6) . ?
C22 C23 1.395(8) . ?
C22 C24 1.378(9) 2_666 ?
C23 C24 1.376(9) . ?
C23 F8 1.348(8) . ?
C24 F9 1.341(7) . ?
C11 C12 1.600(15) . ?
C11 F5 1.399(17) . ?
C11 F6 1.29(2) . ?
C11 F7 1.240(17) . ?
C12 C13 1.359(12) . ?
C12 O2 1.251(9) . ?
C13 C14 1.400(13) . ?
C14 C15 1.594(12) . ?
C14 O1 1.276(9) . ?
C14 C15' 1.376(12) . ?
C25 O5 1.63(2) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 C17 1.3900 . ?
C17 C18 1.3900 . ?
C18 C19 1.3900 . ?
C19 C20 1.3900 . ?
O4 Tb01 2.353(5) . ?
O3 Tb01 2.317(5) . ?
O1 Tb01 2.273(5) . ?
O2 Tb01 2.284(5) . ?
O5 Tb01 2.380(4) . ?
O5 C25' 1.45(2) . ?
O6 Tb01 2.469(5) . ?
O7 Tb01 2.540(4) . ?
O7 Tb01 2.365(4) 2_566 ?
C6' C5' 1.3900 . ?
C6' C7' 1.3900 . ?
C5' C10' 1.3900 . ?
C10' C9' 1.3900 . ?
C9' C8' 1.3900 . ?
C8' C7' 1.3900 . ?
C15' C16' 1.3900 . ?
C15' C20' 1.3900 . ?
C16' C17' 1.3900 . ?
C17' C18' 1.3900 . ?
C18' C19' 1.3900 . ?
C19' C20' 1.3900 . ?

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
C5 C10 C9 120.0 . . ?
C10 C5 C4 116.8(6) . . ?
C6 C5 C10 120.0 . . ?
C6 C5 C4 123.2(6) . . ?
C7 C6 C5 120.0 . . ?
C8 C7 C6 120.0 . . ?
C7 C8 C9 120.0 . . ?
C8 C9 C10 120.0 . . ?
F10 C1 C2 114.8(6) . . ?
F10 C1 F12 120.5(9) . . ?
F10 C1 F1 98.2(8) . . ?
F11 C1 C2 105.2(10) . . ?
F11 C1 F2 133.0(12) . . ?
F12 C1 C2 104.9(8) . . ?
F2 C1 C2 112.3(9) . . ?
F4 C1 C2 119.3(8) . . ?
F4 C1 F11 96.3(14) . . ?
F4 C1 F2 89.3(10) . . ?
F1 C1 C2 110.5(7) . . ?
F1 C1 F12 107.3(8) . . ?
C3 C2 C1 116.6(7) . . ?
O4 C2 C1 114.1(7) . . ?
O4 C2 C3 129.3(8) . . ?
C2 C3 C4 123.6(7) . . ?
C3 C4 C5 117.9(6) . . ?
C3 C4 C5' 124.9(7) . . ?
O3 C4 C5 120.1(6) . . ?
O3 C4 C3 121.9(6) . . ?
O3 C4 C5' 113.1(7) . . ?
C22 C21 Tb01 176.7(4) . . ?
O6 C21 C22 120.2(5) . . ?
O6 C21 O7 120.8(5) . . ?
O6 C21 Tb01 58.7(3) . . ?
O7 C21 C22 119.0(5) . . ?
O7 C21 Tb01 62.1(3) . . ?
C23 C22 C21 121.7(6) . . ?
C24 C22 C21 122.7(5) 2_666 . ?
C24 C22 C23 115.6(5) 2_666 . ?
C24 C23 C22 121.9(6) . . ?
F8 C23 C22 119.8(6) . . ?
F8 C23 C24 118.3(5) . . ?
C23 C24 C22 122.5(5) . 2_666 ?
F9 C24 C22 119.1(5) . 2_666 ?
F9 C24 C23 118.4(6) . . ?
F5 C11 C12 109.4(12) . . ?
F6 C11 C12 113.6(11) . . ?
F6 C11 F5 116.5(12) . . ?
F7 C11 C12 113.4(11) . . ?
F7 C11 F5 101.8(12) . . ?
F7 C11 F6 101.3(16) . . ?
C13 C12 C11 122.0(8) . . ?
O2 C12 C11 110.4(8) . . ?
O2 C12 C13 127.5(8) . . ?
C12 C13 C14 122.3(8) . . ?
C13 C14 C15 128.8(7) . . ?
O1 C14 C13 124.5(7) . . ?
O1 C14 C15 106.5(7) . . ?
O1 C14 C15' 123.2(8) . . ?
C15' C14 C13 112.0(8) . . ?
C16 C15 C14 123.4(7) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C14 116.1(7) . . ?
C15 C16 C17 120.0 . . ?
C18 C17 C16 120.0 . . ?
C17 C18 C19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C19 C20 C15 120.0 . . ?
C2 O4 Tb01 128.1(5) . . ?
C4 O3 Tb01 135.4(4) . . ?
C14 O1 Tb01 134.9(5) . . ?
C12 O2 Tb01 133.6(5) . . ?
C25 O5 Tb01 125.8(9) . . ?
C25' O5 Tb01 126.1(10) . . ?
C21 O6 Tb01 95.6(4) . . ?
C21 O7 Tb01 153.1(4) . 2_566 ?
C21 O7 Tb01 91.8(3) . . ?
Tb01 O7 Tb01 112.98(17) 2_566 . ?
O4 Tb01 C21 83.30(18) . . ?
O4 Tb01 O5 147.12(15) . . ?
O4 Tb01 O6 92.64(18) . . ?
O4 Tb01 O7 81.84(16) . 2_566 ?
O4 Tb01 O7 75.81(15) . . ?
O3 Tb01 C21 98.06(17) . . ?
O3 Tb01 O4 73.19(16) . . ?
O3 Tb01 O5 133.49(15) . . ?
O3 Tb01 O6 78.03(15) . . ?
O3 Tb01 O7 118.41(16) . . ?
O3 Tb01 O7 151.28(15) . 2_566 ?
O1 Tb01 C21 160.06(19) . . ?
O1 Tb01 O4 77.31(19) . . ?
O1 Tb01 O3 80.86(18) . . ?
O1 Tb01 O2 73.75(19) . . ?
O1 Tb01 O5 120.15(19) . . ?
O1 Tb01 O6 158.51(18) . . ?
O1 Tb01 O7 80.00(16) . 2_566 ?
O1 Tb01 O7 139.76(16) . . ?
O2 Tb01 C21 125.56(18) . . ?
O2 Tb01 O4 140.48(16) . . ?
O2 Tb01 O3 76.11(18) . . ?
O2 Tb01 O5 72.11(17) . . ?
O2 Tb01 O6 104.76(18) . . ?
O2 Tb01 O7 118.17(18) . 2_566 ?
O2 Tb01 O7 142.11(15) . . ?
O5 Tb01 C21 74.96(18) . . ?
O5 Tb01 O6 78.28(17) . . ?
O5 Tb01 O7 73.80(15) . . ?
O6 Tb01 C21 25.60(15) . . ?
O6 Tb01 O7 51.79(14) . . ?
O7 Tb01 C21 26.19(15) . . ?
O7 Tb01 C21 92.79(15) 2_566 . ?
O7 Tb01 O5 75.03(15) 2_566 . ?
O7 Tb01 O6 117.77(14) 2_566 . ?
O7 Tb01 O7 67.02(17) 2_566 . ?
C5' C6' C7' 120.0 . . ?
C6' C5' C4 119.9(8) . . ?
C6' C5' C10' 120.0 . . ?
C10' C5' C4 120.1(8) . . ?
C9' C10' C5' 120.0 . . ?
C8' C9' C10' 120.0 . . ?
C9' C8' C7' 120.0 . . ?
C8' C7' C6' 120.0 . . ?
C14 C15' C16' 113.4(8) . . ?
C14 C15' C20' 126.6(8) . . ?
C16' C15' C20' 120.0 . . ?
C17' C16' C15' 120.0 . . ?
C18' C17' C16' 120.0 . . ?
C17' C18' C19' 120.0 . . ?
C18' C19' C20' 120.0 . . ?
C19' C20' C15' 120.0 . . ?

_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_2-pr_sq
_database_code_depnum_ccdc_archive 'CCDC 1569938'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F8 O8 Pr [+ C H4 O]'
_chemical_formula_sum            'C26 H20 F8 O8 Pr [+ C H4 O]'
_chemical_formula_weight         785.37
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pr Pr -0.2180 2.8214 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.084(5)
_cell_length_b                   11.448(5)
_cell_length_c                   15.101(5)
_cell_angle_alpha                103.411(5)
_cell_angle_beta                 95.753(5)
_cell_angle_gamma                114.512(5)
_cell_volume                     1504.4(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    0.747
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5605
_cell_measurement_theta_min      3.5437
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.713
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_correction_T_min  0.717
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.663
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             742
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0627
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9376
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.551
_diffrn_ambient_temperature      293.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4808
_reflns_number_total             5268
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
From the SQUEEZE data output we see that the contribution of some 40 electrons were removed the unit cell by the SQUEEZE process.  With methanol having 18 electrons, this 40-electron value could be in accord with the contribution of some 2.2 MeOH molecules being removed from the unit cell (or 1.1 MeOH molecules per asymmetric unit).
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         4.027
_refine_diff_density_min         -2.516
_refine_diff_density_rms         0.216
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5268
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0877
_refine_ls_R_factor_gt           0.0821
_refine_ls_restrained_S_all      1.170
_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)+(0.0214P)²+47.8786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2172
_refine_ls_wR_factor_ref         0.2204
_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, All O(H) groups
2. Restrained distances
 O8-H8A
 0.85 with sigma of 0.01
 O7-H7A
 0.85 with sigma of 0.01
 C26-H8A
 1.896889 with sigma of 0.02
 Pr1-H8A
 3.014491 with sigma of 0.02
 C25-H7A
 1.873325 with sigma of 0.02
 Pr1-H7A
 3.121421 with sigma of 0.02
3.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.3041(17) 0.8988(15) 0.7695(11) 0.047(4) Uani 1 1 d . . . . .
C2 C 1.1452(14) 0.7821(13) 0.7410(9) 0.036(3) Uani 1 1 d . . . . .
C3 C 1.0465(16) 0.7966(13) 0.7922(9) 0.039(3) Uani 1 1 d . . . . .
H3 H 1.079570 0.876491 0.840279 0.047 Uiso 1 1 calc R . . . .
C4 C 0.8947(15) 0.6970(14) 0.7769(9) 0.036(3) Uani 1 1 d . . . . .
C5 C 0.7995(17) 0.7255(15) 0.8387(10) 0.040(3) Uani 1 1 d . . . . .
C6 C 0.853(2) 0.8099(18) 0.9282(11) 0.057(4) Uani 1 1 d . . . . .
H6 H 0.955875 0.856747 0.951895 0.068 Uiso 1 1 calc R . . . .
C7 C 0.758(3) 0.827(2) 0.9846(14) 0.080(6) Uani 1 1 d . . . . .
H7 H 0.796784 0.885924 1.045150 0.096 Uiso 1 1 calc R . . . .
C8 C 0.607(2) 0.758(2) 0.9499(14) 0.077(6) Uani 1 1 d . . . . .
H8 H 0.542975 0.766662 0.987862 0.092 Uiso 1 1 calc R . . . .
C9 C 0.550(2) 0.675(3) 0.8608(17) 0.093(8) Uani 1 1 d . . . . .
H9 H 0.447292 0.631497 0.838053 0.112 Uiso 1 1 calc R . . . .
C10 C 0.641(2) 0.654(2) 0.8030(13) 0.065(5) Uani 1 1 d . . . . .
H10 H 0.601005 0.594700 0.742698 0.078 Uiso 1 1 calc R . . . .
C11 C 0.903(2) 0.0870(17) 0.7489(13) 0.059(4) Uani 1 1 d . . . . .
C12 C 0.9548(16) 0.2348(14) 0.7585(10) 0.039(3) Uani 1 1 d . . . . .
C13 C 1.0452(19) 0.3278(15) 0.8423(10) 0.050(4) Uani 1 1 d . . . . .
H13 H 1.077567 0.297583 0.888116 0.060 Uiso 1 1 calc R . . . .
C14 C 1.0905(16) 0.4675(14) 0.8610(10) 0.040(3) Uani 1 1 d . . . . .
C15 C 1.1775(14) 0.5627(14) 0.9528(9) 0.035(3) Uani 1 1 d . . . . .
C16 C 1.217(2) 0.523(2) 1.0280(11) 0.065(5) Uani 1 1 d . . . . .
H16 H 1.190305 0.432210 1.019521 0.078 Uiso 1 1 calc R . . . .
C17 C 1.295(3) 0.617(2) 1.1161(13) 0.091(8) Uani 1 1 d . . . . .
H17 H 1.325802 0.589501 1.164267 0.109 Uiso 1 1 calc R . . . .
C18 C 1.326(2) 0.748(2) 1.1308(12) 0.065(5) Uani 1 1 d . . . . .
H18 H 1.371930 0.809708 1.190091 0.078 Uiso 1 1 calc R . . . .
C19 C 1.289(2) 0.7902(18) 1.0573(11) 0.058(4) Uani 1 1 d . . . . .
H19 H 1.316755 0.881312 1.066948 0.069 Uiso 1 1 calc R . . . .
C20 C 1.2133(19) 0.7032(17) 0.9728(10) 0.052(4) Uani 1 1 d . . . . .
H20 H 1.183548 0.733633 0.926265 0.062 Uiso 1 1 calc R . . . .
C21 C 0.7776(15) 0.5269(14) 0.4453(9) 0.037(3) Uani 1 1 d . . . . .
C22 C 0.6335(14) 0.5118(14) 0.4748(9) 0.033(3) Uani 1 1 d . . . . .
C23 C 0.6245(15) 0.6215(16) 0.5319(11) 0.046(4) Uani 1 1 d . . . . .
C24 C 0.4934(16) 0.6113(15) 0.5576(10) 0.043(3) Uani 1 1 d . . . . .
C25 C 0.5726(19) 0.1741(16) 0.5750(15) 0.071(5) Uani 1 1 d D . . . .
H25A H 0.470667 0.153436 0.577163 0.107 Uiso 1 1 calc R . . . .
H25B H 0.579668 0.146972 0.511232 0.107 Uiso 1 1 calc R . . . .
H25C H 0.605310 0.126691 0.609545 0.107 Uiso 1 1 calc R . . . .
C26 C 0.900(2) 0.1330(18) 0.4781(13) 0.067(5) Uani 1 1 d D . . . .
H26A H 0.853737 0.075547 0.415158 0.100 Uiso 1 1 calc R . . . .
H26B H 1.006351 0.162559 0.488308 0.100 Uiso 1 1 calc R . . . .
H26C H 0.860735 0.084083 0.520773 0.100 Uiso 1 1 calc R . . . .
O1 O 0.8382(10) 0.5855(9) 0.7125(7) 0.040(2) Uani 1 1 d . . . . .
O2 O 1.1151(13) 0.6846(10) 0.6721(6) 0.047(3) Uani 1 1 d . . . . .
O3 O 1.0669(8) 0.5262(9) 0.7942(5) 0.032(2) Uani 1 1 d . . . . .
O4 O 0.9099(12) 0.2564(11) 0.6861(7) 0.047(2) Uani 1 1 d . . . . .
O5 O 0.8661(10) 0.4992(10) 0.4927(6) 0.037(2) Uani 1 1 d . . . . .
O6 O 0.8027(10) 0.5630(11) 0.3749(6) 0.041(2) Uani 1 1 d . . . . .
O7 O 0.6639(11) 0.3142(10) 0.6147(8) 0.052(3) Uani 1 1 d D . . . .
H7A H 0.611(4) 0.350(4) 0.637(11) 0.078 Uiso 1 1 d DR . . . .
O8 O 0.8712(12) 0.2484(10) 0.4934(6) 0.045(2) Uani 1 1 d D . . . .
H8A H 0.843(14) 0.254(6) 0.4401(14) 0.067 Uiso 1 1 d DR . . . .
Pr1 Pr 0.94786(8) 0.44668(7) 0.63425(5) 0.0259(2) Uani 1 1 d D . . . .
F1 F 0.7555(16) 0.0167(12) 0.7217(13) 0.120(5) Uani 1 1 d . . . . .
F2 F 0.9566(19) 0.0313(13) 0.6852(11) 0.116(5) Uani 1 1 d . . . . .
F3 F 0.939(2) 0.0611(13) 0.8254(10) 0.129(6) Uani 1 1 d . . . . .
F4 F 0.7482(10) 0.7386(10) 0.5651(8) 0.075(3) Uani 1 1 d . . . . .
F5 F 0.4896(10) 0.7152(10) 0.6126(8) 0.069(3) Uani 1 1 d . . . . .
F6 F 1.3203(14) 1.0080(13) 0.8259(13) 0.144(8) Uani 1 1 d . . . . .
F7 F 1.3580(14) 0.9304(13) 0.7004(9) 0.110(5) Uani 1 1 d . . . . .
F8 F 1.3958(15) 0.8656(18) 0.8112(15) 0.156(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.535(19) . ?
C1 F6 1.275(19) . ?
C1 F7 1.281(18) . ?
C1 F8 1.30(2) . ?
C2 C3 1.360(19) . ?
C2 O2 1.240(16) . ?
C3 C4 1.433(19) . ?
C4 C5 1.482(18) . ?
C4 O1 1.269(16) . ?
C5 C6 1.37(2) . ?
C5 C10 1.43(2) . ?
C6 C7 1.39(2) . ?
C7 C8 1.37(3) . ?
C8 C9 1.36(3) . ?
C9 C10 1.38(2) . ?
C11 C12 1.51(2) . ?
C11 F1 1.33(2) . ?
C11 F2 1.32(2) . ?
C11 F3 1.31(2) . ?
C12 C13 1.38(2) . ?
C12 O4 1.257(16) . ?
C13 C14 1.42(2) . ?
C14 C15 1.463(19) . ?
C14 O3 1.387(17) . ?
C15 C16 1.40(2) . ?
C15 C20 1.44(2) . ?
C16 C17 1.41(3) . ?
C17 C18 1.36(3) . ?
C18 C19 1.39(2) . ?
C19 C20 1.34(2) . ?
C21 C22 1.516(17) . ?
C21 O5 1.273(16) . ?
C21 O6 1.240(16) . ?
C21 Pr1 3.056(13) 2_766 ?
C22 C23 1.392(19) . ?
C22 C24 1.39(2) 2_666 ?
C23 C24 1.381(19) . ?
C23 F4 1.334(17) . ?
C24 F5 1.301(16) . ?
C25 O7 1.413(18) . ?
C26 O8 1.443(18) . ?
O1 Pr1 2.448(8) . ?
O2 Pr1 2.421(10) . ?
O3 Pr1 2.366(8) . ?
O4 Pr1 2.380(10) . ?
O5 Pr1 2.503(9) . ?
O5 Pr1 2.808(8) 2_766 ?
O6 Pr1 2.579(9) 2_766 ?
O7 Pr1 2.570(10) . ?
O8 Pr1 2.500(9) . ?

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
F6 C1 C2 115.6(13) . . ?
F6 C1 F7 106.1(16) . . ?
F6 C1 F8 105.4(17) . . ?
F7 C1 C2 113.8(13) . . ?
F7 C1 F8 104.9(16) . . ?
F8 C1 C2 110.2(14) . . ?
C3 C2 C1 116.6(12) . . ?
O2 C2 C1 118.3(13) . . ?
O2 C2 C3 125.0(13) . . ?
C2 C3 C4 124.3(12) . . ?
C3 C4 C5 118.7(12) . . ?
O1 C4 C3 122.8(12) . . ?
O1 C4 C5 118.5(12) . . ?
C6 C5 C4 124.1(14) . . ?
C6 C5 C10 118.7(14) . . ?
C10 C5 C4 117.1(13) . . ?
C5 C6 C7 121.7(18) . . ?
C8 C7 C6 119.0(18) . . ?
C9 C8 C7 120.9(17) . . ?
C8 C9 C10 121.6(19) . . ?
C9 C10 C5 118.1(17) . . ?
F1 C11 C12 112.0(15) . . ?
F2 C11 C12 111.6(15) . . ?
F2 C11 F1 105.6(17) . . ?
F3 C11 C12 115.2(15) . . ?
F3 C11 F1 105.6(17) . . ?
F3 C11 F2 106.2(16) . . ?
C13 C12 C11 117.9(13) . . ?
O4 C12 C11 113.9(13) . . ?
O4 C12 C13 128.1(13) . . ?
C12 C13 C14 122.4(13) . . ?
C13 C14 C15 121.2(13) . . ?
O3 C14 C13 123.8(12) . . ?
O3 C14 C15 114.8(12) . . ?
C16 C15 C14 123.0(14) . . ?
C16 C15 C20 116.1(14) . . ?
C20 C15 C14 120.5(12) . . ?
C15 C16 C17 121.2(18) . . ?
C18 C17 C16 119.9(17) . . ?
C17 C18 C19 119.8(16) . . ?
C20 C19 C18 121.7(17) . . ?
C19 C20 C15 121.0(15) . . ?
C22 C21 Pr1 174.1(9) . 2_766 ?
O5 C21 C22 118.6(12) . . ?
O5 C21 Pr1 66.7(7) . 2_766 ?
O6 C21 C22 118.5(12) . . ?
O6 C21 O5 122.9(12) . . ?
O6 C21 Pr1 56.1(6) . 2_766 ?
C23 C22 C21 120.9(13) . . ?
C24 C22 C21 120.1(12) 2_666 . ?
C24 C22 C23 118.9(12) 2_666 . ?
C24 C23 C22 122.0(13) . . ?
F4 C23 C22 118.5(12) . . ?
F4 C23 C24 119.4(13) . . ?
C23 C24 C22 119.1(13) . 2_666 ?
F5 C24 C22 120.5(12) . 2_666 ?
F5 C24 C23 120.4(14) . . ?
C4 O1 Pr1 132.3(8) . . ?
C2 O2 Pr1 132.4(10) . . ?
C14 O3 Pr1 135.5(8) . . ?
C12 O4 Pr1 137.2(10) . . ?
C21 O5 Pr1 88.7(7) . 2_766 ?
C21 O5 Pr1 151.3(8) . . ?
Pr1 O5 Pr1 119.7(3) . 2_766 ?
C21 O6 Pr1 100.3(8) . 2_766 ?
C25 O7 Pr1 128.1(9) . . ?
C26 O8 Pr1 131.4(10) . . ?
O1 Pr1 C21 140.7(4) . 2_766 ?
O1 Pr1 O5 84.0(3) . . ?
O1 Pr1 O5 127.7(3) . 2_766 ?
O1 Pr1 O6 143.3(3) . 2_766 ?
O1 Pr1 O7 67.3(3) . . ?
O1 Pr1 O8 137.8(3) . . ?
O2 Pr1 C21 72.5(4) . 2_766 ?
O2 Pr1 O1 68.4(3) . . ?
O2 Pr1 O5 78.4(3) . . ?
O2 Pr1 O5 68.0(3) . 2_766 ?
O2 Pr1 O6 80.1(3) . 2_766 ?
O2 Pr1 O7 132.8(3) . . ?
O2 Pr1 O8 133.8(3) . . ?
O3 Pr1 C21 97.5(3) . 2_766 ?
O3 Pr1 O1 74.1(3) . . ?
O3 Pr1 O2 72.0(3) . . ?
O3 Pr1 O4 72.1(3) . . ?
O3 Pr1 O5 116.8(3) . 2_766 ?
O3 Pr1 O5 148.0(3) . . ?
O3 Pr1 O6 78.8(3) . 2_766 ?
O3 Pr1 O7 109.7(3) . . ?
O3 Pr1 O8 140.3(3) . . ?
O4 Pr1 C21 98.2(4) . 2_766 ?
O4 Pr1 O1 114.5(3) . . ?
O4 Pr1 O2 141.2(3) . . ?
O4 Pr1 O5 139.4(3) . . ?
O4 Pr1 O5 117.4(3) . 2_766 ?
O4 Pr1 O6 79.0(3) . 2_766 ?
O4 Pr1 O7 74.1(4) . . ?
O4 Pr1 O8 72.1(3) . . ?
O5 Pr1 C21 84.8(3) . 2_766 ?
O5 Pr1 C21 24.6(3) 2_766 2_766 ?
O5 Pr1 O5 60.3(3) . 2_766 ?
O5 Pr1 O6 108.2(3) . 2_766 ?
O5 Pr1 O7 81.7(4) . . ?
O6 Pr1 C21 23.5(3) 2_766 2_766 ?
O6 Pr1 O5 48.1(3) 2_766 2_766 ?
O7 Pr1 C21 147.1(3) . 2_766 ?
O7 Pr1 O5 133.4(3) . 2_766 ?
O7 Pr1 O6 147.1(3) . 2_766 ?
O8 Pr1 C21 71.3(4) . 2_766 ?
O8 Pr1 O5 67.1(3) . 2_766 ?
O8 Pr1 O5 70.7(3) . . ?
O8 Pr1 O6 78.1(3) . 2_766 ?
O8 Pr1 O7 75.9(3) . . ?

_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_4-sm_sq
_database_code_depnum_ccdc_archive 'CCDC 1569940'
_audit_update_record             
;
2018-04-03 deposited with the CCDC.
2018-04-11 downloaded from the CCDC.
;
_audit_creation_date             2017-12-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H20 F8 O8 Sm [+ C H4 O]'
_chemical_formula_sum            'C26 H20 F8 O8 Sm [+ C H4 O]'
_chemical_formula_weight         762.77
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.072(5)
_cell_length_b                   11.411(5)
_cell_length_c                   15.022(5)
_cell_angle_alpha                103.577(5)
_cell_angle_beta                 95.627(5)
_cell_angle_gamma                114.432(5)
_cell_volume                     1490.4(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4727
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.5628
_cell_measurement_theta_min      3.2334
_shelx_estimated_absorpt_T_max   0.747
_shelx_estimated_absorpt_T_min   0.708
_exptl_absorpt_coefficient_mu    2.064
_exptl_absorpt_correction_T_max  0.734
_exptl_absorpt_correction_T_min  0.697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9862
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.240
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  MoKα
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4817
_reflns_number_total             5240
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
 From the SQUEEZE data output we see that the contribution of some 31 electrons were removed the unit cell by the SQUEEZE process.  With methanol having 18 electrons, this 31 electron value could be in accord with the contribution of some 1.8 MeOH molecules being removed from the unit cell (or ~0.9 MeOH molecules per asymmetric unit).
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'Bruker SHELXTL'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.846
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     394
_refine_ls_number_reflns         5240
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+1.1860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0852
_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, All O(H) groups
2. Restrained distances
 O8-H8A
 0.85 with sigma of 0.01
 O7-H7A
 0.85 with sigma of 0.01
 C26-H8A
 1.887157 with sigma of 0.02
 Sm1-H8A
 2.960054 with sigma of 0.02
 C25-H7A
 1.88493 with sigma of 0.02
 Sm1-H7A
 3.050598 with sigma of 0.02
3. Rigid bond restraints
 C7, C8
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4.a Me refined with riding coordinates:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C16(H16),
 C17(H17), C18(H18), C19(H19), C20(H20)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.3006(6) 0.8948(5) 0.7666(3) 0.0488(12) Uani 1 1 d . . . . .
C2 C 1.1436(5) 0.7809(4) 0.7397(3) 0.0364(10) Uani 1 1 d . . . . .
C3 C 1.0429(5) 0.7943(5) 0.7913(3) 0.0391(10) Uani 1 1 d . . . . .
H3 H 1.074294 0.874524 0.839410 0.047 Uiso 1 1 calc R . . . .
C4 C 0.8938(5) 0.6935(5) 0.7759(3) 0.0378(10) Uani 1 1 d . . . . .
C5 C 0.7947(5) 0.7201(5) 0.8373(3) 0.0429(11) Uani 1 1 d . . . . .
C6 C 0.8535(6) 0.8096(6) 0.9276(4) 0.0548(13) Uani 1 1 d . . . . .
H6 H 0.956411 0.857584 0.950549 0.066 Uiso 1 1 calc R . . . .
C7 C 0.7564(8) 0.8267(7) 0.9835(4) 0.0754(18) Uani 1 1 d . U . . .
H7 H 0.794022 0.882847 1.045200 0.091 Uiso 1 1 calc R . . . .
C8 C 0.6062(8) 0.7611(8) 0.9475(5) 0.092(2) Uani 1 1 d . U . . .
H8 H 0.541906 0.776263 0.983764 0.110 Uiso 1 1 calc R . . . .
C9 C 0.5498(7) 0.6741(8) 0.8595(5) 0.086(2) Uani 1 1 d . . . . .
H9 H 0.446839 0.627312 0.836424 0.103 Uiso 1 1 calc R . . . .
C10 C 0.6437(6) 0.6547(6) 0.8041(4) 0.0620(15) Uani 1 1 d . . . . .
H10 H 0.603979 0.596197 0.743103 0.074 Uiso 1 1 calc R . . . .
C11 C 0.9050(7) 0.0866(6) 0.7469(4) 0.0616(15) Uani 1 1 d . . . . .
C12 C 0.9590(5) 0.2358(5) 0.7579(3) 0.0430(11) Uani 1 1 d . . . . .
C13 C 1.0463(6) 0.3299(5) 0.8416(3) 0.0490(12) Uani 1 1 d . . . . .
H13 H 1.075163 0.300284 0.889285 0.059 Uiso 1 1 calc R . . . .
C14 C 1.0942(5) 0.4695(5) 0.8587(3) 0.0363(10) Uani 1 1 d . . . . .
C15 C 1.1768(5) 0.5661(5) 0.9539(3) 0.0418(11) Uani 1 1 d . . . . .
C16 C 1.2196(7) 0.5264(6) 1.0268(4) 0.0690(17) Uani 1 1 d . . . . .
H16 H 1.198544 0.436385 1.017169 0.083 Uiso 1 1 calc R . . . .
C17 C 1.2940(8) 0.6201(7) 1.1147(4) 0.082(2) Uani 1 1 d . . . . .
H17 H 1.321176 0.592070 1.163774 0.098 Uiso 1 1 calc R . . . .
C18 C 1.3281(7) 0.7545(7) 1.1299(4) 0.0653(16) Uani 1 1 d . . . . .
H18 H 1.379450 0.817193 1.188595 0.078 Uiso 1 1 calc R . . . .
C19 C 1.2861(6) 0.7936(6) 1.0586(4) 0.0590(14) Uani 1 1 d . . . . .
H19 H 1.308117 0.883809 1.068049 0.071 Uiso 1 1 calc R . . . .
C20 C 1.2094(6) 0.6990(5) 0.9706(3) 0.0501(12) Uani 1 1 d . . . . .
H20 H 1.179916 0.727106 0.922313 0.060 Uiso 1 1 calc R . . . .
C21 C 0.7782(4) 0.5243(4) 0.4482(3) 0.0315(9) Uani 1 1 d . . . . .
C22 C 0.6346(4) 0.5114(4) 0.4761(3) 0.0296(9) Uani 1 1 d . . . . .
C23 C 0.6261(4) 0.6201(5) 0.5343(3) 0.0391(10) Uani 1 1 d . . . . .
C24 C 0.4931(5) 0.6085(5) 0.5576(3) 0.0372(10) Uani 1 1 d . . . . .
C25 C 0.5765(6) 0.1725(6) 0.5757(5) 0.0716(17) Uani 1 1 d D . . . .
H25A H 0.475282 0.153949 0.578846 0.107 Uiso 1 1 calc R . . . .
H25B H 0.582163 0.144328 0.511378 0.107 Uiso 1 1 calc R . . . .
H25C H 0.608225 0.124169 0.610160 0.107 Uiso 1 1 calc R . . . .
C26 C 0.9019(7) 0.1366(6) 0.4778(4) 0.0604(15) Uani 1 1 d D . . . .
H26A H 0.854256 0.080167 0.414301 0.091 Uiso 1 1 calc R . . . .
H26B H 1.007742 0.165716 0.487100 0.091 Uiso 1 1 calc R . . . .
H26C H 0.862817 0.086397 0.520190 0.091 Uiso 1 1 calc R . . . .
O1 O 0.8390(3) 0.5804(3) 0.7133(2) 0.0397(7) Uani 1 1 d . . . . .
O2 O 1.1229(3) 0.6815(3) 0.67081(19) 0.0380(7) Uani 1 1 d . . . . .
O3 O 1.0663(3) 0.5180(3) 0.79687(19) 0.0404(7) Uani 1 1 d . . . . .
O4 O 0.9136(4) 0.2564(3) 0.6842(2) 0.0429(7) Uani 1 1 d . . . . .
O5 O 0.8626(3) 0.4966(3) 0.49696(19) 0.0352(7) Uani 1 1 d . . . . .
O6 O 0.8061(3) 0.5611(3) 0.3775(2) 0.0422(7) Uani 1 1 d . . . . .
O7 O 0.6714(4) 0.3141(3) 0.6156(3) 0.0521(9) Uani 1 1 d D . . . .
H7A H 0.619(2) 0.350(2) 0.640(4) 0.078 Uiso 1 1 d DR . . . .
O8 O 0.8737(4) 0.2516(3) 0.4955(2) 0.0432(7) Uani 1 1 d D . . . .
H8A H 0.855(5) 0.263(3) 0.4423(9) 0.065 Uiso 1 1 d DR . . . .
Sm1 Sm 0.94903(2) 0.44608(2) 0.63510(2) 0.02724(9) Uani 1 1 d D . . . .
F1 F 0.7587(5) 0.0180(4) 0.7193(4) 0.1111(15) Uani 1 1 d . . . . .
F2 F 0.9604(6) 0.0323(4) 0.6841(4) 0.1159(16) Uani 1 1 d . . . . .
F3 F 0.9408(7) 0.0620(4) 0.8252(3) 0.129(2) Uani 1 1 d . . . . .
F4 F 0.7491(3) 0.7380(3) 0.5688(3) 0.0745(10) Uani 1 1 d . . . . .
F5 F 0.4889(3) 0.7156(3) 0.6142(2) 0.0645(9) Uani 1 1 d . . . . .
F6 F 1.3163(5) 1.0066(4) 0.8212(4) 0.147(3) Uani 1 1 d . . . . .
F7 F 1.3564(4) 0.9221(5) 0.6958(3) 0.1074(16) Uani 1 1 d . . . . .
F8 F 1.3941(5) 0.8630(6) 0.8088(4) 0.152(3) 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(6) . ?
C1 F6 1.281(6) . ?
C1 F7 1.294(6) . ?
C1 F8 1.302(7) . ?
C2 C3 1.371(6) . ?
C2 O2 1.270(5) . ?
C3 C4 1.417(6) . ?
C4 C5 1.497(6) . ?
C4 O1 1.262(5) . ?
C5 C6 1.388(7) . ?
C5 C10 1.362(7) . ?
C6 C7 1.393(7) . ?
C7 C8 1.361(9) . ?
C8 C9 1.351(9) . ?
C9 C10 1.371(8) . ?
C11 C12 1.518(7) . ?
C11 F1 1.314(7) . ?
C11 F2 1.304(7) . ?
C11 F3 1.322(6) . ?
C12 C13 1.370(7) . ?
C12 O4 1.266(5) . ?
C13 C14 1.409(7) . ?
C14 C15 1.491(6) . ?
C14 O3 1.252(5) . ?
C15 C16 1.376(7) . ?
C15 C20 1.364(7) . ?
C16 C17 1.389(8) . ?
C17 C18 1.380(9) . ?
C18 C19 1.349(8) . ?
C19 C20 1.396(7) . ?
C21 C22 1.504(5) . ?
C21 O5 1.252(5) . ?
C21 O6 1.247(5) . ?
C21 Sm1 3.055(4) 2_766 ?
C22 C23 1.379(6) . ?
C22 C24 1.369(6) 2_666 ?
C23 C24 1.379(6) . ?
C23 F4 1.335(5) . ?
C24 F5 1.334(5) . ?
C25 O7 1.427(6) . ?
C26 O8 1.427(6) . ?
O1 Sm1 2.402(3) . ?
O2 Sm1 2.412(3) . ?
O3 Sm1 2.382(3) . ?
O4 Sm1 2.349(3) . ?
O5 Sm1 2.453(3) . ?
O5 Sm1 2.878(3) 2_766 ?
O6 Sm1 2.525(3) 2_766 ?
O7 Sm1 2.514(3) . ?
O8 Sm1 2.451(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F6 C1 C2 114.9(5) . . ?
F6 C1 F7 106.6(5) . . ?
F6 C1 F8 106.5(6) . . ?
F7 C1 C2 114.0(4) . . ?
F7 C1 F8 102.7(5) . . ?
F8 C1 C2 111.2(5) . . ?
C3 C2 C1 118.2(4) . . ?
O2 C2 C1 113.9(4) . . ?
O2 C2 C3 128.0(4) . . ?
C2 C3 C4 124.0(4) . . ?
C3 C4 C5 119.0(4) . . ?
O1 C4 C3 123.7(4) . . ?
O1 C4 C5 117.3(4) . . ?
C6 C5 C4 121.3(4) . . ?
C10 C5 C4 119.4(5) . . ?
C10 C5 C6 119.3(5) . . ?
C5 C6 C7 119.2(5) . . ?
C8 C7 C6 119.8(6) . . ?
C9 C8 C7 120.6(6) . . ?
C8 C9 C10 120.2(6) . . ?
C5 C10 C9 120.8(6) . . ?
F1 C11 C12 112.0(5) . . ?
F1 C11 F3 106.0(5) . . ?
F2 C11 C12 111.3(5) . . ?
F2 C11 F1 106.6(5) . . ?
F2 C11 F3 106.8(5) . . ?
F3 C11 C12 113.7(5) . . ?
C13 C12 C11 119.6(4) . . ?
O4 C12 C11 112.6(4) . . ?
O4 C12 C13 127.8(5) . . ?
C12 C13 C14 122.8(4) . . ?
C13 C14 C15 120.5(4) . . ?
O3 C14 C13 122.5(4) . . ?
O3 C14 C15 116.9(4) . . ?
C16 C15 C14 122.5(5) . . ?
C20 C15 C14 119.2(4) . . ?
C20 C15 C16 118.2(5) . . ?
C15 C16 C17 120.3(6) . . ?
C18 C17 C16 120.7(5) . . ?
C19 C18 C17 119.1(5) . . ?
C18 C19 C20 120.1(6) . . ?
C15 C20 C19 121.6(5) . . ?
C22 C21 Sm1 171.6(3) . 2_766 ?
O5 C21 C22 118.2(4) . . ?
O5 C21 Sm1 70.0(2) . 2_766 ?
O6 C21 C22 118.2(3) . . ?
O6 C21 O5 123.7(4) . . ?
O6 C21 Sm1 53.7(2) . 2_766 ?
C23 C22 C21 121.4(4) . . ?
C24 C22 C21 120.7(4) 2_666 . ?
C24 C22 C23 117.9(4) 2_666 . ?
C22 C23 C24 121.1(4) . . ?
F4 C23 C22 119.3(4) . . ?
F4 C23 C24 119.6(4) . . ?
C22 C24 C23 121.0(4) 2_666 . ?
F5 C24 C22 119.5(4) . 2_666 ?
F5 C24 C23 119.6(4) . . ?
C4 O1 Sm1 132.7(3) . . ?
C2 O2 Sm1 129.1(3) . . ?
C14 O3 Sm1 139.6(3) . . ?
C12 O4 Sm1 136.2(3) . . ?
C21 O5 Sm1 154.6(3) . . ?
C21 O5 Sm1 85.9(2) . 2_766 ?
Sm1 O5 Sm1 119.05(10) . 2_766 ?
C21 O6 Sm1 102.9(2) . 2_766 ?
C25 O7 Sm1 129.9(3) . . ?
C26 O8 Sm1 132.4(3) . . ?
O1 Sm1 C21 140.68(11) . 2_766 ?
O1 Sm1 O2 71.38(11) . . ?
O1 Sm1 O5 127.75(10) . 2_766 ?
O1 Sm1 O5 83.28(10) . . ?
O1 Sm1 O6 143.80(11) . 2_766 ?
O1 Sm1 O7 67.22(11) . . ?
O1 Sm1 O8 137.38(11) . . ?
O2 Sm1 C21 69.61(11) . 2_766 ?
O2 Sm1 O5 65.82(9) . 2_766 ?
O2 Sm1 O5 79.31(10) . . ?
O2 Sm1 O6 77.20(11) . 2_766 ?
O2 Sm1 O7 135.58(11) . . ?
O2 Sm1 O8 132.08(10) . . ?
O3 Sm1 C21 98.51(11) . 2_766 ?
O3 Sm1 O1 75.24(10) . . ?
O3 Sm1 O2 74.29(10) . . ?
O3 Sm1 O5 150.09(11) . . ?
O3 Sm1 O5 118.01(10) . 2_766 ?
O3 Sm1 O6 79.38(10) . 2_766 ?
O3 Sm1 O7 108.99(11) . . ?
O3 Sm1 O8 138.59(11) . . ?
O4 Sm1 C21 98.51(11) . 2_766 ?
O4 Sm1 O1 114.83(11) . . ?
O4 Sm1 O2 140.62(11) . . ?
O4 Sm1 O3 70.54(11) . . ?
O4 Sm1 O5 138.63(10) . . ?
O4 Sm1 O5 117.18(10) . 2_766 ?
O4 Sm1 O6 79.43(11) . 2_766 ?
O4 Sm1 O7 74.06(12) . . ?
O4 Sm1 O8 71.56(11) . . ?
O5 Sm1 C21 85.00(10) . 2_766 ?
O5 Sm1 C21 24.13(9) 2_766 2_766 ?
O5 Sm1 O5 60.95(10) . 2_766 ?
O5 Sm1 O6 108.34(9) . 2_766 ?
O5 Sm1 O7 80.59(11) . . ?
O6 Sm1 C21 23.46(10) 2_766 2_766 ?
O6 Sm1 O5 47.59(8) 2_766 2_766 ?
O7 Sm1 C21 146.52(11) . 2_766 ?
O7 Sm1 O5 132.82(10) . 2_766 ?
O7 Sm1 O6 147.07(12) . 2_766 ?
O8 Sm1 C21 71.28(11) . 2_766 ?
O8 Sm1 O5 70.73(10) . . ?
O8 Sm1 O5 67.08(10) . 2_766 ?
O8 Sm1 O6 77.89(11) . 2_766 ?
O8 Sm1 O7 75.45(11) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
