# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_dal219
_database_code_depnum_ccdc_archive 'CCDC 2313982'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Er F18 N4 O3'
_chemical_formula_sum            'C21 H15 Er F18 N4 O3'
_chemical_formula_weight         880.63
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   8.1560(8)
_cell_length_b                   14.0106(14)
_cell_length_c                   14.8598(15)
_cell_angle_alpha                117.742(5)
_cell_angle_beta                 93.538(5)
_cell_angle_gamma                91.261(5)
_cell_volume                     1497.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    31416
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.423
_cell_measurement_theta_min      2.506
_shelx_estimated_absorpt_T_max   0.957
_shelx_estimated_absorpt_T_min   0.532
_exptl_absorpt_coefficient_mu    2.945
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0680 before and 0.0454 after correction.
The Ratio of minimum to maximum transmission is 0.8036.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    ?
_exptl_crystal_density_diffrn    1.953
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             846
_exptl_crystal_size_max          0.245
_exptl_crystal_size_mid          0.025
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_unetI/netI     0.0232
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            31416
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.423
_diffrn_reflns_theta_min         2.506
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex'
_diffrn_measurement_method       'CCD Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5723
_reflns_number_total             6126
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.290
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         6126
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0266
_refine_ls_R_factor_gt           0.0241
_refine_ls_restrained_S_all      1.068
_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)+(0.0292P)²+2.5289P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0605
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C11(H11A,H11B), C31(H31A,H31B), C12(H12A,
 H12B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C24(H24), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Er1 Er 0.67153(2) 0.68307(2) 0.37272(2) 0.01744(5) Uani 1 1 d . . . . .
F16 F 0.5657(3) 0.64845(16) 0.70304(15) 0.0313(4) Uani 1 1 d . . . . .
F24 F 0.3484(2) 0.90512(17) 0.22524(16) 0.0322(4) Uani 1 1 d . . . . .
F25 F 0.5258(3) 1.02865(15) 0.33370(16) 0.0312(4) Uani 1 1 d . . . . .
F36 F 0.4994(3) 0.40446(16) 0.00133(14) 0.0343(5) Uani 1 1 d . . . . .
F15 F 0.4228(2) 0.78436(16) 0.72391(16) 0.0323(4) Uani 1 1 d . . . . .
F31 F 1.0829(2) 0.46549(17) 0.39761(17) 0.0346(5) Uani 1 1 d . . . . .
O2 O 0.8326(3) 0.68330(18) 0.25758(17) 0.0249(5) Uani 1 1 d . . . . .
F33 F 0.9012(3) 0.33893(19) 0.3636(2) 0.0410(5) Uani 1 1 d . . . . .
F14 F 0.6592(3) 0.80941(19) 0.80534(15) 0.0389(5) Uani 1 1 d . . . . .
O1 O 0.8290(3) 0.81806(19) 0.49312(17) 0.0293(5) Uani 1 1 d . . . . .
F35 F 0.4282(3) 0.29780(17) 0.06083(16) 0.0397(5) Uani 1 1 d . . . . .
F26 F 0.5617(3) 0.95145(19) 0.17410(17) 0.0406(5) Uani 1 1 d . . . . .
F32 F 1.0534(3) 0.3318(2) 0.24770(18) 0.0453(6) Uani 1 1 d . . . . .
F12 F 0.9391(3) 1.03634(18) 0.6300(2) 0.0497(6) Uani 1 1 d . . . . .
O3 O 0.7988(3) 0.54408(18) 0.37004(17) 0.0262(5) Uani 1 1 d . . . . .
F11 F 1.1252(3) 0.92569(19) 0.5774(2) 0.0521(7) Uani 1 1 d . . . . .
F34 F 0.6639(3) 0.2884(2) 0.00146(17) 0.0495(6) Uani 1 1 d . . . . .
N2 N 0.5659(3) 0.8198(2) 0.33123(19) 0.0193(5) Uani 1 1 d . . . . .
F22 F 1.0792(3) 0.6549(2) 0.13243(18) 0.0534(7) Uani 1 1 d . . . . .
F23 F 0.9248(4) 0.6991(3) 0.0386(2) 0.0796(11) Uani 1 1 d . . . . .
F13 F 1.0503(4) 0.9795(3) 0.7271(2) 0.0718(10) Uani 1 1 d . . . . .
N4 N 0.3575(3) 0.6804(2) 0.37008(19) 0.0181(5) Uani 1 1 d . . . . .
N1 N 0.5888(3) 0.6989(2) 0.5341(2) 0.0195(5) Uani 1 1 d . . . . .
N3 N 0.5504(3) 0.5241(2) 0.2189(2) 0.0211(5) Uani 1 1 d . . . . .
F21 F 0.8654(4) 0.5589(3) 0.0474(2) 0.0788(10) Uani 1 1 d . . . . .
C21 C 0.2941(4) 0.7731(2) 0.3574(2) 0.0210(6) Uani 1 1 d . . . . .
H21A H 0.196450 0.799553 0.396576 0.025 Uiso 1 1 calc R U . . .
H21B H 0.260740 0.749185 0.284579 0.025 Uiso 1 1 calc R U . . .
C14 C 0.7935(4) 0.8297(2) 0.6554(2) 0.0215(6) Uani 1 1 d . . . . .
H14 H 0.839482 0.861674 0.724045 0.026 Uiso 1 1 calc R U . . .
C22 C 0.4277(4) 0.8635(2) 0.3954(2) 0.0215(6) Uani 1 1 d . . . . .
H22A H 0.386239 0.926295 0.389328 0.026 Uiso 1 1 calc R U . . .
H22B H 0.463474 0.887011 0.467892 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6533(4) 0.7551(2) 0.6267(2) 0.0193(6) Uani 1 1 d . . . . .
C25 C 0.8220(4) 0.7197(3) 0.1933(2) 0.0223(6) Uani 1 1 d . . . . .
C23 C 0.6030(4) 0.8465(2) 0.2621(2) 0.0193(6) Uani 1 1 d . . . . .
C24 C 0.7245(4) 0.7970(3) 0.1920(2) 0.0231(6) Uani 1 1 d . . . . .
H24 H 0.738364 0.819129 0.141363 0.028 Uiso 1 1 calc R U . . .
C15 C 0.8641(4) 0.8570(2) 0.5893(2) 0.0223(6) Uani 1 1 d . . . . .
C11 C 0.3084(4) 0.6885(3) 0.4686(2) 0.0208(6) Uani 1 1 d . . . . .
H11A H 0.197444 0.653092 0.457988 0.025 Uiso 1 1 calc R U . . .
H11B H 0.304186 0.765393 0.519373 0.025 Uiso 1 1 calc R U . . .
C36 C 0.9710(4) 0.3976(3) 0.3251(3) 0.0267(7) Uani 1 1 d . . . . .
C16 C 0.9961(4) 0.9496(3) 0.6319(3) 0.0268(7) Uani 1 1 d . . . . .
C31 C 0.2864(4) 0.5768(2) 0.2841(2) 0.0216(6) Uani 1 1 d . . . . .
H31A H 0.170363 0.585450 0.266800 0.026 Uiso 1 1 calc R U . . .
H31B H 0.287774 0.519801 0.305765 0.026 Uiso 1 1 calc R U . . .
C33 C 0.6267(4) 0.4390(2) 0.1629(2) 0.0220(6) Uani 1 1 d . . . . .
C17 C 0.5760(4) 0.7501(3) 0.7161(2) 0.0260(7) Uani 1 1 d . . . . .
C12 C 0.4318(4) 0.6342(3) 0.5085(2) 0.0212(6) Uani 1 1 d . . . . .
H12A H 0.393855 0.632438 0.569714 0.025 Uiso 1 1 calc R U . . .
H12B H 0.445063 0.559141 0.455691 0.025 Uiso 1 1 calc R U . . .
C35 C 0.8409(4) 0.4571(3) 0.2951(2) 0.0221(6) Uani 1 1 d . . . . .
C34 C 0.7763(4) 0.4086(3) 0.1959(3) 0.0247(7) Uani 1 1 d . . . . .
H34 H 0.833309 0.351952 0.146416 0.030 Uiso 1 1 calc R U . . .
C27 C 0.5102(4) 0.9333(3) 0.2482(3) 0.0253(7) Uani 1 1 d . . . . .
C32 C 0.3819(4) 0.5420(3) 0.1902(2) 0.0233(7) Uani 1 1 d . . . . .
H32A H 0.330072 0.474734 0.133182 0.028 Uiso 1 1 calc R U . . .
H32B H 0.383919 0.598952 0.168460 0.028 Uiso 1 1 calc R U . . .
C37 C 0.5540(4) 0.3569(3) 0.0559(3) 0.0275(7) Uani 1 1 d . . . . .
C26 C 0.9283(5) 0.6633(3) 0.1045(3) 0.0365(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
Er1 O2 2.222(2) . ?
Er1 O1 2.211(2) . ?
Er1 O3 2.212(2) . ?
Er1 N2 2.428(3) . ?
Er1 N4 2.558(2) . ?
Er1 N1 2.443(3) . ?
Er1 N3 2.458(3) . ?
F16 C17 1.345(4) . ?
F24 C27 1.346(4) . ?
F25 C27 1.344(4) . ?
F36 C37 1.332(4) . ?
F15 C17 1.340(4) . ?
F31 C36 1.336(4) . ?
O2 C25 1.275(4) . ?
F33 C36 1.336(4) . ?
F14 C17 1.322(4) . ?
O1 C15 1.280(4) . ?
F35 C37 1.331(4) . ?
F26 C27 1.330(4) . ?
F32 C36 1.327(4) . ?
F12 C16 1.322(4) . ?
O3 C35 1.283(4) . ?
F11 C16 1.321(4) . ?
F34 C37 1.335(4) . ?
N2 C22 1.475(4) . ?
N2 C23 1.296(4) . ?
F22 C26 1.301(4) . ?
F23 C26 1.290(5) . ?
F13 C16 1.318(4) . ?
N4 C21 1.494(4) . ?
N4 C11 1.495(4) . ?
N4 C31 1.490(4) . ?
N1 C13 1.293(4) . ?
N1 C12 1.474(4) . ?
N3 C33 1.294(4) . ?
N3 C32 1.476(4) . ?
F21 C26 1.371(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.519(4) . ?
C14 H14 0.9500 . ?
C14 C13 1.433(4) . ?
C14 C15 1.361(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C13 C17 1.535(4) . ?
C25 C24 1.364(5) . ?
C25 C26 1.522(5) . ?
C23 C24 1.426(4) . ?
C23 C27 1.532(4) . ?
C24 H24 0.9500 . ?
C15 C16 1.528(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.524(4) . ?
C36 C35 1.532(4) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.520(4) . ?
C33 C34 1.433(4) . ?
C33 C37 1.534(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C35 C34 1.366(5) . ?
C34 H34 0.9500 . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Er1 N2 75.41(8) . . ?
O2 Er1 N4 129.22(8) . . ?
O2 Er1 N1 159.64(9) . . ?
O2 Er1 N3 79.66(9) . . ?
O1 Er1 O2 89.16(9) . . ?
O1 Er1 O3 100.17(9) . . ?
O1 Er1 N2 84.81(9) . . ?
O1 Er1 N4 121.69(9) . . ?
O1 Er1 N1 74.39(9) . . ?
O1 Er1 N3 167.61(9) . . ?
O3 Er1 O2 89.49(8) . . ?
O3 Er1 N2 164.10(8) . . ?
O3 Er1 N4 118.89(8) . . ?
O3 Er1 N1 81.91(8) . . ?
O3 Er1 N3 74.63(9) . . ?
N2 Er1 N4 69.34(8) . . ?
N2 Er1 N1 113.99(8) . . ?
N2 Er1 N3 97.37(9) . . ?
N1 Er1 N4 70.74(8) . . ?
N1 Er1 N3 115.27(9) . . ?
N3 Er1 N4 70.19(8) . . ?
C25 O2 Er1 134.5(2) . . ?
C15 O1 Er1 137.1(2) . . ?
C35 O3 Er1 130.9(2) . . ?
C22 N2 Er1 105.36(18) . . ?
C23 N2 Er1 131.0(2) . . ?
C23 N2 C22 123.3(3) . . ?
C21 N4 Er1 110.59(17) . . ?
C21 N4 C11 109.4(2) . . ?
C11 N4 Er1 108.70(17) . . ?
C31 N4 Er1 109.23(17) . . ?
C31 N4 C21 109.6(2) . . ?
C31 N4 C11 109.3(2) . . ?
C13 N1 Er1 131.3(2) . . ?
C13 N1 C12 123.0(3) . . ?
C12 N1 Er1 105.58(18) . . ?
C33 N3 Er1 125.6(2) . . ?
C33 N3 C32 122.7(3) . . ?
C32 N3 Er1 111.29(18) . . ?
N4 C21 H21A 109.8 . . ?
N4 C21 H21B 109.8 . . ?
N4 C21 C22 109.5(2) . . ?
H21A C21 H21B 108.2 . . ?
C22 C21 H21A 109.8 . . ?
C22 C21 H21B 109.8 . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C15 C14 C13 123.4(3) . . ?
N2 C22 C21 106.7(2) . . ?
N2 C22 H22A 110.4 . . ?
N2 C22 H22B 110.4 . . ?
C21 C22 H22A 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
N1 C13 C14 124.2(3) . . ?
N1 C13 C17 121.0(3) . . ?
C14 C13 C17 114.7(3) . . ?
O2 C25 C24 128.8(3) . . ?
O2 C25 C26 113.6(3) . . ?
C24 C25 C26 117.5(3) . . ?
N2 C23 C24 124.2(3) . . ?
N2 C23 C27 120.6(3) . . ?
C24 C23 C27 115.2(3) . . ?
C25 C24 C23 124.0(3) . . ?
C25 C24 H24 118.0 . . ?
C23 C24 H24 118.0 . . ?
O1 C15 C14 128.2(3) . . ?
O1 C15 C16 113.2(3) . . ?
C14 C15 C16 118.6(3) . . ?
N4 C11 H11A 109.7 . . ?
N4 C11 H11B 109.7 . . ?
N4 C11 C12 110.1(2) . . ?
H11A C11 H11B 108.2 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 109.7 . . ?
F31 C36 F33 106.0(3) . . ?
F31 C36 C35 112.3(3) . . ?
F33 C36 C35 110.5(3) . . ?
F32 C36 F31 106.6(3) . . ?
F32 C36 F33 107.8(3) . . ?
F32 C36 C35 113.3(3) . . ?
F12 C16 C15 110.9(3) . . ?
F11 C16 F12 105.7(3) . . ?
F11 C16 C15 112.3(3) . . ?
F13 C16 F12 106.6(3) . . ?
F13 C16 F11 107.4(3) . . ?
F13 C16 C15 113.5(3) . . ?
N4 C31 H31A 109.3 . . ?
N4 C31 H31B 109.3 . . ?
N4 C31 C32 111.6(3) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.3 . . ?
C32 C31 H31B 109.3 . . ?
N3 C33 C34 124.4(3) . . ?
N3 C33 C37 121.2(3) . . ?
C34 C33 C37 114.2(3) . . ?
F16 C17 C13 111.2(3) . . ?
F15 C17 F16 107.2(3) . . ?
F15 C17 C13 110.7(3) . . ?
F14 C17 F16 106.5(3) . . ?
F14 C17 F15 107.2(3) . . ?
F14 C17 C13 113.6(3) . . ?
N1 C12 C11 106.6(2) . . ?
N1 C12 H12A 110.4 . . ?
N1 C12 H12B 110.4 . . ?
C11 C12 H12A 110.4 . . ?
C11 C12 H12B 110.4 . . ?
H12A C12 H12B 108.6 . . ?
O3 C35 C36 114.1(3) . . ?
O3 C35 C34 128.3(3) . . ?
C34 C35 C36 117.4(3) . . ?
C33 C34 H34 118.4 . . ?
C35 C34 C33 123.2(3) . . ?
C35 C34 H34 118.4 . . ?
F24 C27 C23 111.0(3) . . ?
F25 C27 F24 107.3(3) . . ?
F25 C27 C23 111.5(3) . . ?
F26 C27 F24 106.6(3) . . ?
F26 C27 F25 106.5(3) . . ?
F26 C27 C23 113.5(3) . . ?
N3 C32 C31 106.8(2) . . ?
N3 C32 H32A 110.4 . . ?
N3 C32 H32B 110.4 . . ?
C31 C32 H32A 110.4 . . ?
C31 C32 H32B 110.4 . . ?
H32A C32 H32B 108.6 . . ?
F36 C37 F34 106.1(3) . . ?
F36 C37 C33 112.1(3) . . ?
F35 C37 F36 107.4(3) . . ?
F35 C37 F34 107.2(3) . . ?
F35 C37 C33 111.2(3) . . ?
F34 C37 C33 112.5(3) . . ?
F22 C26 F21 104.9(3) . . ?
F22 C26 C25 113.6(3) . . ?
F23 C26 F22 110.6(3) . . ?
F23 C26 F21 102.6(4) . . ?
F23 C26 C25 115.9(3) . . ?
F21 C26 C25 107.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Er1 O2 C25 C24 19.5(5) . . . . ?
Er1 O2 C25 C26 -157.2(2) . . . . ?
Er1 O1 C15 C14 -8.1(5) . . . . ?
Er1 O1 C15 C16 175.5(2) . . . . ?
Er1 O3 C35 C36 162.3(2) . . . . ?
Er1 O3 C35 C34 -22.9(5) . . . . ?
Er1 N2 C22 C21 -67.0(2) . . . . ?
Er1 N2 C23 C24 -0.7(5) . . . . ?
Er1 N2 C23 C27 176.8(2) . . . . ?
Er1 N4 C21 C22 -24.5(3) . . . . ?
Er1 N4 C11 C12 -31.7(3) . . . . ?
Er1 N4 C31 C32 -38.4(3) . . . . ?
Er1 N1 C13 C14 3.6(4) . . . . ?
Er1 N1 C13 C17 -179.7(2) . . . . ?
Er1 N1 C12 C11 -64.0(2) . . . . ?
Er1 N3 C33 C34 19.4(4) . . . . ?
Er1 N3 C33 C37 -165.3(2) . . . . ?
Er1 N3 C32 C31 -53.5(3) . . . . ?
F31 C36 C35 O3 -37.4(4) . . . . ?
F31 C36 C35 C34 147.2(3) . . . . ?
O2 C25 C24 C23 -5.2(6) . . . . ?
O2 C25 C26 F22 -48.6(5) . . . . ?
O2 C25 C26 F23 -178.3(4) . . . . ?
O2 C25 C26 F21 67.3(4) . . . . ?
F33 C36 C35 O3 80.7(4) . . . . ?
F33 C36 C35 C34 -94.7(4) . . . . ?
O1 C15 C16 F12 69.5(4) . . . . ?
O1 C15 C16 F11 -48.5(4) . . . . ?
O1 C15 C16 F13 -170.6(3) . . . . ?
F32 C36 C35 O3 -158.3(3) . . . . ?
F32 C36 C35 C34 26.3(4) . . . . ?
O3 C35 C34 C33 -11.5(5) . . . . ?
N2 C23 C24 C25 -3.7(5) . . . . ?
N2 C23 C27 F24 -59.7(4) . . . . ?
N2 C23 C27 F25 59.9(4) . . . . ?
N2 C23 C27 F26 -179.7(3) . . . . ?
N4 C21 C22 N2 61.7(3) . . . . ?
N4 C11 C12 N1 66.0(3) . . . . ?
N4 C31 C32 N3 62.3(3) . . . . ?
N1 C13 C17 F16 57.7(4) . . . . ?
N1 C13 C17 F15 -61.4(4) . . . . ?
N1 C13 C17 F14 177.9(3) . . . . ?
N3 C33 C34 C35 10.5(5) . . . . ?
N3 C33 C37 F36 46.6(4) . . . . ?
N3 C33 C37 F35 -73.7(4) . . . . ?
N3 C33 C37 F34 166.1(3) . . . . ?
C21 N4 C11 C12 -152.6(2) . . . . ?
C21 N4 C31 C32 82.9(3) . . . . ?
C14 C13 C17 F16 -125.3(3) . . . . ?
C14 C13 C17 F15 115.5(3) . . . . ?
C14 C13 C17 F14 -5.1(4) . . . . ?
C14 C15 C16 F12 -107.3(3) . . . . ?
C14 C15 C16 F11 134.6(3) . . . . ?
C14 C15 C16 F13 12.6(4) . . . . ?
C22 N2 C23 C24 -173.0(3) . . . . ?
C22 N2 C23 C27 4.5(4) . . . . ?
C13 N1 C12 C11 112.1(3) . . . . ?
C13 C14 C15 O1 -5.3(5) . . . . ?
C13 C14 C15 C16 170.9(3) . . . . ?
C23 N2 C22 C21 107.0(3) . . . . ?
C24 C25 C26 F22 134.3(4) . . . . ?
C24 C25 C26 F23 4.5(5) . . . . ?
C24 C25 C26 F21 -109.8(4) . . . . ?
C24 C23 C27 F24 118.1(3) . . . . ?
C24 C23 C27 F25 -122.3(3) . . . . ?
C24 C23 C27 F26 -2.0(4) . . . . ?
C15 C14 C13 N1 6.6(5) . . . . ?
C15 C14 C13 C17 -170.2(3) . . . . ?
C11 N4 C21 C22 95.2(3) . . . . ?
C11 N4 C31 C32 -157.2(2) . . . . ?
C36 C35 C34 C33 163.1(3) . . . . ?
C31 N4 C21 C22 -145.0(3) . . . . ?
C31 N4 C11 C12 87.4(3) . . . . ?
C33 N3 C32 C31 132.8(3) . . . . ?
C12 N1 C13 C14 -171.4(3) . . . . ?
C12 N1 C13 C17 5.2(4) . . . . ?
C34 C33 C37 F36 -137.6(3) . . . . ?
C34 C33 C37 F35 102.1(3) . . . . ?
C34 C33 C37 F34 -18.1(4) . . . . ?
C27 C23 C24 C25 178.6(3) . . . . ?
C32 N3 C33 C34 -167.9(3) . . . . ?
C32 N3 C33 C37 7.4(5) . . . . ?
C37 C33 C34 C35 -165.1(3) . . . . ?
C26 C25 C24 C23 171.4(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.128 0.000 0.000 185.1 37.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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_dal2071
_database_code_depnum_ccdc_archive 'CCDC 2313983'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 F18 N4 O3 Yb'
_chemical_formula_sum            'C21 H15 F18 N4 O3 Yb'
_chemical_formula_weight         886.41
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.1775(18)
_cell_length_b                   10.2981(10)
_cell_length_c                   17.0455(17)
_cell_angle_alpha                90
_cell_angle_beta                 116.043(5)
_cell_angle_gamma                90
_cell_volume                     2866.8(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    36260
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      20.75
_cell_measurement_theta_min      2.383
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.477
_exptl_absorpt_coefficient_mu    3.412
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7414
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.7414.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    2.054
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'colorless plate-like'
_exptl_crystal_F_000             1700
_exptl_crystal_size_max          0.255
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.025
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0736
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            34970
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.318
_diffrn_reflns_theta_min         2.660
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex'
_diffrn_measurement_method       'CCD Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4094
_reflns_number_total             5785
_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       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.880
_refine_diff_density_min         -1.393
_refine_diff_density_rms         0.150
_refine_ls_extinction_coef       0.00077(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     425
_refine_ls_number_reflns         5785
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0699
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.028
_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)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C21(H21A,H21B), C22(H22A,H22B), C31(H31A,
 H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C24(H24), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Yb1 Yb 0.25424(2) 0.64519(2) 0.43405(2) 0.02067(9) Uani 1 1 d . . . . .
F11 F 0.1462(3) 1.0018(4) 0.2700(3) 0.0711(12) Uani 1 1 d . . . . .
F12 F 0.0552(3) 1.0615(4) 0.3080(2) 0.0846(15) Uani 1 1 d . . . . .
F13 F 0.0283(2) 0.9183(4) 0.2095(2) 0.0666(11) Uani 1 1 d . . . . .
F14 F 0.0222(2) 0.8799(3) 0.5296(2) 0.0526(10) Uani 1 1 d . . . . .
F15 F -0.0034(2) 0.6775(3) 0.5093(2) 0.0473(9) Uani 1 1 d . . . . .
F16 F 0.10389(19) 0.7441(3) 0.62035(19) 0.0405(8) Uani 1 1 d . . . . .
F21 F 0.4475(2) 1.0663(4) 0.5494(3) 0.0895(15) Uani 1 1 d . . . . .
F22 F 0.3295(3) 1.0567(3) 0.4458(3) 0.0702(12) Uani 1 1 d . . . . .
F23 F 0.3440(3) 1.0728(3) 0.5759(2) 0.0695(12) Uani 1 1 d . . . . .
F24 F 0.5948(2) 0.7040(4) 0.6476(2) 0.0608(11) Uani 1 1 d . . . . .
F25 F 0.55548(19) 0.5118(3) 0.60116(19) 0.0415(8) Uani 1 1 d . . . . .
F26 F 0.5454(2) 0.5819(3) 0.7148(2) 0.0516(10) Uani 1 1 d . . . . .
F31 F 0.3614(3) 0.9110(3) 0.2915(2) 0.0650(11) Uani 1 1 d . . . . .
F32 F 0.3494(2) 0.7989(4) 0.1834(2) 0.0672(12) Uani 1 1 d . . . . .
F33 F 0.4474(2) 0.7630(4) 0.3080(3) 0.0689(12) Uani 1 1 d . . . . .
F34 F 0.1879(2) 0.4466(4) 0.0960(2) 0.0732(13) Uani 1 1 d . . . . .
F35 F 0.2315(2) 0.2928(4) 0.1910(2) 0.0647(11) Uani 1 1 d . . . . .
F36 F 0.1129(2) 0.3768(3) 0.1536(2) 0.0571(10) Uani 1 1 d . . . . .
O1 O 0.1539(2) 0.7613(3) 0.3381(2) 0.0297(9) Uani 1 1 d . . . . .
O2 O 0.3006(2) 0.8241(3) 0.5073(2) 0.0242(8) Uani 1 1 d . . . . .
O3 O 0.3271(2) 0.7058(3) 0.3676(2) 0.0275(9) Uani 1 1 d . . . . .
N1 N 0.1539(3) 0.6566(4) 0.4921(3) 0.0255(10) Uani 1 1 d . . . . .
N2 N 0.3881(3) 0.5874(4) 0.5467(2) 0.0206(10) Uani 1 1 d . . . . .
N3 N 0.2230(3) 0.4879(4) 0.3177(3) 0.0263(10) Uani 1 1 d . . . . .
N4 N 0.2449(3) 0.4290(4) 0.4924(3) 0.0237(10) Uani 1 1 d . . . . .
C11 C 0.1705(3) 0.4237(5) 0.5078(3) 0.0300(13) Uani 1 1 d . . . . .
H11A H 0.174874 0.348934 0.546125 0.036 Uiso 1 1 calc R U . . .
H11B H 0.121777 0.410040 0.451466 0.036 Uiso 1 1 calc R U . . .
C12 C 0.1595(3) 0.5468(5) 0.5497(3) 0.0292(13) Uani 1 1 d . . . . .
H12A H 0.108938 0.541274 0.557958 0.035 Uiso 1 1 calc R U . . .
H12B H 0.206524 0.559183 0.607583 0.035 Uiso 1 1 calc R U . . .
C13 C 0.1056(3) 0.7549(5) 0.4821(3) 0.0262(13) Uani 1 1 d . . . . .
C14 C 0.0912(3) 0.8567(5) 0.4209(3) 0.0298(13) Uani 1 1 d . . . . .
H14 H 0.064781 0.933209 0.426659 0.036 Uiso 1 1 calc R U . . .
C15 C 0.1136(3) 0.8501(5) 0.3538(3) 0.0293(13) Uani 1 1 d . . . . .
C16 C 0.0864(4) 0.9593(6) 0.2856(4) 0.0427(16) Uani 1 1 d . . . . .
C17 C 0.0573(4) 0.7643(5) 0.5349(4) 0.0331(14) Uani 1 1 d . . . . .
C21 C 0.3191(3) 0.4048(5) 0.5757(3) 0.0298(14) Uani 1 1 d . . . . .
H21A H 0.322962 0.310836 0.589281 0.036 Uiso 1 1 calc R U . . .
H21B H 0.313682 0.451717 0.623619 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3967(3) 0.4484(5) 0.5712(3) 0.0285(13) Uani 1 1 d . . . . .
H22A H 0.444384 0.435963 0.628600 0.034 Uiso 1 1 calc R U . . .
H22B H 0.405553 0.396331 0.527256 0.034 Uiso 1 1 calc R U . . .
C23 C 0.4505(3) 0.6659(5) 0.5782(3) 0.0244(12) Uani 1 1 d . . . . .
C24 C 0.4440(3) 0.8027(5) 0.5647(3) 0.0285(13) Uani 1 1 d . . . . .
H24 H 0.493112 0.849927 0.578697 0.034 Uiso 1 1 calc R U . . .
C25 C 0.3726(3) 0.8704(5) 0.5331(3) 0.0263(13) Uani 1 1 d . . . . .
C26 C 0.3739(4) 1.0156(6) 0.5276(4) 0.0429(16) Uani 1 1 d . . . . .
C27 C 0.5374(4) 0.6161(5) 0.6359(4) 0.0368(15) Uani 1 1 d . . . . .
C31 C 0.2375(3) 0.3262(5) 0.4272(3) 0.0337(15) Uani 1 1 d . . . . .
H31A H 0.213035 0.247134 0.439115 0.040 Uiso 1 1 calc R U . . .
H31B H 0.292689 0.303409 0.433392 0.040 Uiso 1 1 calc R U . . .
C32 C 0.1848(4) 0.3717(5) 0.3346(3) 0.0364(15) Uani 1 1 d . . . . .
H32A H 0.180322 0.302125 0.292666 0.044 Uiso 1 1 calc R U . . .
H32B H 0.128996 0.392785 0.327400 0.044 Uiso 1 1 calc R U . . .
C33 C 0.2284(3) 0.5035(6) 0.2442(3) 0.0333(14) Uani 1 1 d . . . . .
C34 C 0.2721(3) 0.6083(5) 0.2285(3) 0.0339(14) Uani 1 1 d . . . . .
H34 H 0.268643 0.617321 0.171510 0.041 Uiso 1 1 calc R U . . .
C35 C 0.3178(3) 0.6943(5) 0.2897(3) 0.0252(13) Uani 1 1 d . . . . .
C36 C 0.3693(4) 0.7924(6) 0.2680(4) 0.0392(15) Uani 1 1 d . . . . .
C37 C 0.1906(4) 0.4044(7) 0.1711(4) 0.0489(18) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.193(3) . ?
Yb1 O2 2.177(3) . ?
Yb1 O3 2.177(3) . ?
Yb1 N1 2.431(4) . ?
Yb1 N2 2.420(4) . ?
Yb1 N3 2.427(4) . ?
Yb1 N4 2.474(4) . ?
Yb1 C15 3.128(5) . ?
Yb1 C25 3.109(5) . ?
Yb1 C35 3.184(5) . ?
F11 C16 1.304(7) . ?
F12 C16 1.329(6) . ?
F13 C16 1.332(7) . ?
F14 C17 1.335(6) . ?
F15 C17 1.336(6) . ?
F16 C17 1.341(6) . ?
F21 C26 1.327(7) . ?
F22 C26 1.337(7) . ?
F23 C26 1.308(6) . ?
F24 C27 1.329(6) . ?
F25 C27 1.336(6) . ?
F26 C27 1.336(6) . ?
F31 C36 1.313(6) . ?
F32 C36 1.325(6) . ?
F33 C36 1.313(7) . ?
F34 C37 1.333(7) . ?
F35 C37 1.330(7) . ?
F36 C37 1.339(7) . ?
O1 C15 1.271(6) . ?
O2 C25 1.276(6) . ?
O3 C35 1.268(5) . ?
N1 C12 1.471(6) . ?
N1 C13 1.300(6) . ?
N2 C22 1.481(6) . ?
N2 C23 1.301(6) . ?
N3 C32 1.475(6) . ?
N3 C33 1.308(6) . ?
N4 C11 1.487(6) . ?
N4 C21 1.488(6) . ?
N4 C31 1.498(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.511(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.420(7) . ?
C13 C17 1.512(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.374(7) . ?
C15 C16 1.535(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.515(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.424(7) . ?
C23 C27 1.536(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.361(7) . ?
C25 C26 1.499(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.517(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.434(7) . ?
C33 C37 1.521(8) . ?
C34 H34 0.9500 . ?
C34 C35 1.342(7) . ?
C35 C36 1.530(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Yb1 N1 75.54(13) . . ?
O1 Yb1 N2 160.47(13) . . ?
O1 Yb1 N3 86.26(13) . . ?
O1 Yb1 N4 127.52(13) . . ?
O1 Yb1 C15 18.92(12) . . ?
O1 Yb1 C25 98.53(14) . . ?
O1 Yb1 C35 78.59(12) . . ?
O2 Yb1 O1 87.25(12) . . ?
O2 Yb1 O3 83.43(12) . . ?
O2 Yb1 N1 84.04(13) . . ?
O2 Yb1 N2 75.63(12) . . ?
O2 Yb1 N3 157.86(13) . . ?
O2 Yb1 N4 127.46(12) . . ?
O2 Yb1 C15 73.52(13) . . ?
O2 Yb1 C25 19.27(13) . . ?
O2 Yb1 C35 97.39(13) . . ?
O3 Yb1 O1 87.26(12) . . ?
O3 Yb1 N1 159.14(13) . . ?
O3 Yb1 N2 81.61(13) . . ?
O3 Yb1 N3 75.14(13) . . ?
O3 Yb1 N4 129.17(13) . . ?
O3 Yb1 C15 98.39(13) . . ?
O3 Yb1 C25 68.60(13) . . ?
O3 Yb1 C35 16.84(13) . . ?
N1 Yb1 N4 71.55(13) . . ?
N1 Yb1 C15 61.98(13) . . ?
N1 Yb1 C25 101.94(14) . . ?
N1 Yb1 C35 154.00(13) . . ?
N2 Yb1 N1 111.21(13) . . ?
N2 Yb1 N3 106.11(13) . . ?
N2 Yb1 N4 71.49(13) . . ?
N2 Yb1 C15 148.92(13) . . ?
N2 Yb1 C25 62.47(13) . . ?
N2 Yb1 C35 94.16(13) . . ?
N3 Yb1 N1 114.63(14) . . ?
N3 Yb1 N4 72.27(13) . . ?
N3 Yb1 C15 103.85(14) . . ?
N3 Yb1 C25 143.08(14) . . ?
N3 Yb1 C35 60.56(14) . . ?
N4 Yb1 C15 126.55(14) . . ?
N4 Yb1 C25 127.31(13) . . ?
N4 Yb1 C35 124.45(13) . . ?
C15 Yb1 C35 93.38(13) . . ?
C25 Yb1 C15 88.39(14) . . ?
C25 Yb1 C35 84.38(14) . . ?
C15 O1 Yb1 127.0(3) . . ?
C25 O2 Yb1 126.5(3) . . ?
C35 O3 Yb1 133.3(3) . . ?
C12 N1 Yb1 113.0(3) . . ?
C13 N1 Yb1 124.6(3) . . ?
C13 N1 C12 122.1(4) . . ?
C22 N2 Yb1 114.0(3) . . ?
C23 N2 Yb1 124.5(3) . . ?
C23 N2 C22 121.2(4) . . ?
C32 N3 Yb1 110.1(3) . . ?
C33 N3 Yb1 127.7(4) . . ?
C33 N3 C32 121.8(4) . . ?
C11 N4 Yb1 109.4(3) . . ?
C11 N4 C21 109.8(4) . . ?
C11 N4 C31 108.2(4) . . ?
C21 N4 Yb1 110.0(3) . . ?
C21 N4 C31 109.7(4) . . ?
C31 N4 Yb1 109.7(3) . . ?
N4 C11 H11A 109.2 . . ?
N4 C11 H11B 109.2 . . ?
N4 C11 C12 111.8(4) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
N1 C12 C11 108.3(4) . . ?
N1 C12 H12A 110.0 . . ?
N1 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
N1 C13 C14 124.6(5) . . ?
N1 C13 C17 120.4(5) . . ?
C14 C13 C17 114.9(5) . . ?
C13 C14 H14 118.4 . . ?
C15 C14 C13 123.2(5) . . ?
C15 C14 H14 118.4 . . ?
O1 C15 Yb1 34.0(2) . . ?
O1 C15 C14 128.3(5) . . ?
O1 C15 C16 113.1(5) . . ?
C14 C15 Yb1 98.8(3) . . ?
C14 C15 C16 118.6(5) . . ?
C16 C15 Yb1 139.1(4) . . ?
F11 C16 F12 107.0(6) . . ?
F11 C16 F13 106.4(5) . . ?
F11 C16 C15 112.3(5) . . ?
F12 C16 F13 106.0(5) . . ?
F12 C16 C15 113.6(5) . . ?
F13 C16 C15 111.1(5) . . ?
F14 C17 F15 105.8(5) . . ?
F14 C17 F16 105.5(4) . . ?
F14 C17 C13 113.7(5) . . ?
F15 C17 F16 106.8(4) . . ?
F15 C17 C13 112.0(4) . . ?
F16 C17 C13 112.5(4) . . ?
N4 C21 H21A 109.2 . . ?
N4 C21 H21B 109.2 . . ?
N4 C21 C22 112.1(4) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
N2 C22 C21 108.4(4) . . ?
N2 C22 H22A 110.0 . . ?
N2 C22 H22B 110.0 . . ?
C21 C22 H22A 110.0 . . ?
C21 C22 H22B 110.0 . . ?
H22A C22 H22B 108.4 . . ?
N2 C23 C24 123.5(5) . . ?
N2 C23 C27 121.5(5) . . ?
C24 C23 C27 115.0(5) . . ?
C23 C24 H24 117.7 . . ?
C25 C24 C23 124.6(5) . . ?
C25 C24 H24 117.7 . . ?
O2 C25 Yb1 34.3(2) . . ?
O2 C25 C24 126.9(5) . . ?
O2 C25 C26 113.2(5) . . ?
C24 C25 Yb1 98.3(3) . . ?
C24 C25 C26 119.8(5) . . ?
C26 C25 Yb1 137.5(4) . . ?
F21 C26 F22 103.9(5) . . ?
F21 C26 C25 114.7(5) . . ?
F22 C26 C25 111.2(5) . . ?
F23 C26 F21 107.0(5) . . ?
F23 C26 F22 106.7(5) . . ?
F23 C26 C25 112.8(5) . . ?
F24 C27 F25 106.5(5) . . ?
F24 C27 F26 107.3(5) . . ?
F24 C27 C23 112.9(5) . . ?
F25 C27 F26 107.2(4) . . ?
F25 C27 C23 111.6(5) . . ?
F26 C27 C23 111.1(5) . . ?
N4 C31 H31A 109.4 . . ?
N4 C31 H31B 109.4 . . ?
N4 C31 C32 111.3(4) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
N3 C32 C31 108.5(4) . . ?
N3 C32 H32A 110.0 . . ?
N3 C32 H32B 110.0 . . ?
C31 C32 H32A 110.0 . . ?
C31 C32 H32B 110.0 . . ?
H32A C32 H32B 108.4 . . ?
N3 C33 C34 123.5(5) . . ?
N3 C33 C37 120.4(5) . . ?
C34 C33 C37 116.1(5) . . ?
C33 C34 H34 118.1 . . ?
C35 C34 C33 123.8(5) . . ?
C35 C34 H34 118.1 . . ?
O3 C35 Yb1 29.8(2) . . ?
O3 C35 C34 128.9(5) . . ?
O3 C35 C36 112.2(5) . . ?
C34 C35 Yb1 100.7(3) . . ?
C34 C35 C36 118.9(5) . . ?
C36 C35 Yb1 139.5(4) . . ?
F31 C36 F32 105.8(5) . . ?
F31 C36 C35 112.3(5) . . ?
F32 C36 C35 113.2(5) . . ?
F33 C36 F31 107.1(5) . . ?
F33 C36 F32 107.1(5) . . ?
F33 C36 C35 111.0(5) . . ?
F34 C37 F36 105.3(5) . . ?
F34 C37 C33 112.4(6) . . ?
F35 C37 F34 107.9(5) . . ?
F35 C37 F36 106.9(6) . . ?
F35 C37 C33 111.7(5) . . ?
F36 C37 C33 112.1(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Yb1 O1 C15 C14 -34.9(8) . . . . ?
Yb1 O1 C15 C16 146.8(4) . . . . ?
Yb1 O2 C25 C24 -38.6(7) . . . . ?
Yb1 O2 C25 C26 142.6(4) . . . . ?
Yb1 O3 C35 C34 -22.0(8) . . . . ?
Yb1 O3 C35 C36 159.9(4) . . . . ?
Yb1 N1 C12 C11 -43.4(5) . . . . ?
Yb1 N1 C13 C14 14.5(7) . . . . ?
Yb1 N1 C13 C17 -167.9(4) . . . . ?
Yb1 N2 C22 C21 -41.5(4) . . . . ?
Yb1 N2 C23 C24 14.1(7) . . . . ?
Yb1 N2 C23 C27 -167.7(3) . . . . ?
Yb1 N3 C32 C31 -50.4(5) . . . . ?
Yb1 N3 C33 C34 15.1(8) . . . . ?
Yb1 N3 C33 C37 -167.9(4) . . . . ?
Yb1 N4 C11 C12 -42.8(5) . . . . ?
Yb1 N4 C21 C22 -42.2(4) . . . . ?
Yb1 N4 C31 C32 -37.5(5) . . . . ?
Yb1 C15 C16 F11 -21.0(9) . . . . ?
Yb1 C15 C16 F12 -142.5(5) . . . . ?
Yb1 C15 C16 F13 98.1(6) . . . . ?
Yb1 C25 C26 F21 -146.1(5) . . . . ?
Yb1 C25 C26 F22 -28.6(8) . . . . ?
Yb1 C25 C26 F23 91.1(7) . . . . ?
Yb1 C35 C36 F31 -33.1(8) . . . . ?
Yb1 C35 C36 F32 -152.9(4) . . . . ?
Yb1 C35 C36 F33 86.7(6) . . . . ?
O1 C15 C16 F11 -48.9(7) . . . . ?
O1 C15 C16 F12 -170.4(5) . . . . ?
O1 C15 C16 F13 70.2(6) . . . . ?
O2 C25 C26 F21 -176.5(5) . . . . ?
O2 C25 C26 F22 -59.0(7) . . . . ?
O2 C25 C26 F23 60.7(7) . . . . ?
O3 C35 C36 F31 -48.4(7) . . . . ?
O3 C35 C36 F32 -168.1(5) . . . . ?
O3 C35 C36 F33 71.5(6) . . . . ?
N1 C13 C14 C15 13.4(9) . . . . ?
N1 C13 C17 F14 168.7(5) . . . . ?
N1 C13 C17 F15 -71.5(6) . . . . ?
N1 C13 C17 F16 48.7(7) . . . . ?
N2 C23 C24 C25 13.6(8) . . . . ?
N2 C23 C27 F24 167.4(5) . . . . ?
N2 C23 C27 F25 47.5(7) . . . . ?
N2 C23 C27 F26 -72.0(6) . . . . ?
N3 C33 C34 C35 6.0(9) . . . . ?
N3 C33 C37 F34 168.0(5) . . . . ?
N3 C33 C37 F35 -70.4(7) . . . . ?
N3 C33 C37 F36 49.6(8) . . . . ?
N4 C11 C12 N1 58.4(5) . . . . ?
N4 C21 C22 N2 56.2(5) . . . . ?
N4 C31 C32 N3 60.1(5) . . . . ?
C11 N4 C21 C22 -162.6(4) . . . . ?
C11 N4 C31 C32 81.8(5) . . . . ?
C12 N1 C13 C14 -173.2(5) . . . . ?
C12 N1 C13 C17 4.4(8) . . . . ?
C13 N1 C12 C11 143.4(5) . . . . ?
C13 C14 C15 Yb1 -24.0(6) . . . . ?
C13 C14 C15 O1 -5.1(9) . . . . ?
C13 C14 C15 C16 173.2(5) . . . . ?
C14 C13 C17 F14 -13.5(7) . . . . ?
C14 C13 C17 F15 106.4(5) . . . . ?
C14 C13 C17 F16 -133.4(5) . . . . ?
C14 C15 C16 F11 132.7(6) . . . . ?
C14 C15 C16 F12 11.1(8) . . . . ?
C14 C15 C16 F13 -108.3(6) . . . . ?
C17 C13 C14 C15 -164.3(5) . . . . ?
C21 N4 C11 C12 77.9(5) . . . . ?
C21 N4 C31 C32 -158.5(4) . . . . ?
C22 N2 C23 C24 -172.7(4) . . . . ?
C22 N2 C23 C27 5.5(7) . . . . ?
C23 N2 C22 C21 144.7(4) . . . . ?
C23 C24 C25 Yb1 -23.9(5) . . . . ?
C23 C24 C25 O2 -3.1(9) . . . . ?
C23 C24 C25 C26 175.6(5) . . . . ?
C24 C23 C27 F24 -14.2(7) . . . . ?
C24 C23 C27 F25 -134.1(5) . . . . ?
C24 C23 C27 F26 106.3(5) . . . . ?
C24 C25 C26 F21 4.6(8) . . . . ?
C24 C25 C26 F22 122.1(6) . . . . ?
C24 C25 C26 F23 -118.2(6) . . . . ?
C27 C23 C24 C25 -164.7(5) . . . . ?
C31 N4 C11 C12 -162.4(4) . . . . ?
C31 N4 C21 C22 78.6(5) . . . . ?
C32 N3 C33 C34 -173.5(5) . . . . ?
C32 N3 C33 C37 3.5(8) . . . . ?
C33 N3 C32 C31 136.8(5) . . . . ?
C33 C34 C35 Yb1 -15.7(6) . . . . ?
C33 C34 C35 O3 -4.8(9) . . . . ?
C33 C34 C35 C36 173.2(5) . . . . ?
C34 C33 C37 F34 -14.7(8) . . . . ?
C34 C33 C37 F35 106.8(6) . . . . ?
C34 C33 C37 F36 -133.2(6) . . . . ?
C34 C35 C36 F31 133.3(5) . . . . ?
C34 C35 C36 F32 13.5(8) . . . . ?
C34 C35 C36 F33 -106.9(6) . . . . ?
C37 C33 C34 C35 -171.1(5) . . . . ?

_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_dal2123
_database_code_depnum_ccdc_archive 'CCDC 2313985'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C30 H35 F21 N4 O3'
_chemical_formula_sum            'C30 H35 F21 N4 O3'
_chemical_formula_weight         898.62
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.9357(12)
_cell_length_b                   13.2583(13)
_cell_length_c                   14.1754(14)
_cell_angle_alpha                102.461(5)
_cell_angle_beta                 98.735(5)
_cell_angle_gamma                115.475(5)
_cell_volume                     1899.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.944
_cell_measurement_theta_min      2.323
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.978
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0588 before and 0.0479 after correction.
The Ratio of minimum to maximum transmission is 0.9666.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            38051
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_min         1.967
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5152
_reflns_number_total             7792
_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       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.0031(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     614
_refine_ls_number_reflns         7792
_refine_ls_number_restraints     279
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.060
_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)+(0.0454P)²+1.0778P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1256
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 F33-C29 \\sim F33A-C29A
 with sigma of 0.01
 F34-C29 \\sim F34A-C29A
 with sigma of 0.01
 C28-C29 \\sim C28-C29A
 with sigma of 0.01
 F33-F34 \\sim F33A-F34A
 with sigma of 0.01
 F33-C28 \\sim F33A-C28
 with sigma of 0.01
 F34-C28 \\sim F34A-C28
 with sigma of 0.01
 F36-C30 \\sim F36A-C30
 with sigma of 0.01
 F35-C30 \\sim F35A-C30
 with sigma of 0.01
 C30-F37 \\sim C30-F37A
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
F35 \\sim F36 \\sim F37 \\sim F35A \\sim F36A \\sim F37A \\sim C30: within 2A
with sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
F33 \\sim F34 \\sim F33A \\sim F34A \\sim C29 \\sim C29A: within 2A with sigma
of 0.02 and sigma for terminal atoms of 0.04 within 2A
F25A \\sim F26A \\sim F27A \\sim C22 \\sim F25B \\sim F26B \\sim F27B: within
2A with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Rigid body (RIGU) restrains
 F35, F36, F37, F35A, F36A, F37A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 F33, F34, F33A, F34A, C29, C29A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 F25A, F26A, F27A, C22, F25B, F26B, F27B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C29A)=Sof(F33A)=Sof(F34A)=Sof(F35A)=Sof(F36A)=Sof(F37A)=1-FVAR(1)
 Sof(F33)=Sof(F34)=Sof(F35)=Sof(F36)=Sof(F37)=Sof(C29)=FVAR(1)
 Sof(F25B)=Sof(F26B)=Sof(F27B)=1-FVAR(2)
 Sof(F25A)=Sof(F26A)=Sof(F27A)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C8(H8), C18(H18)
6.c Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C24(H24A,H24B,
 H24C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_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
F11 F 0.29221(12) 0.14111(12) -0.06524(9) 0.0451(3) Uani 1 1 d . . . . .
F12 F 0.22515(13) 0.03667(12) 0.03287(12) 0.0562(4) Uani 1 1 d . . . . .
F13 F 0.31263(15) 0.25039(15) 0.18748(10) 0.0598(4) Uani 1 1 d . . . . .
F14 F 0.35255(14) 0.33767(12) 0.07388(11) 0.0540(4) Uani 1 1 d . . . . .
F15 F 0.09245(16) 0.17748(19) -0.03868(12) 0.0839(6) Uani 1 1 d . . . . .
F16 F 0.12899(17) 0.30257(18) 0.10069(14) 0.0866(6) Uani 1 1 d . . . . .
F17 F 0.06518(17) 0.1229(2) 0.08992(17) 0.0967(7) Uani 1 1 d . . . . .
F21 F 0.8262(2) 0.72303(13) 0.40513(12) 0.0758(5) Uani 1 1 d . . . . .
F22 F 0.89387(14) 0.66192(14) 0.28347(13) 0.0633(4) Uani 1 1 d . . . . .
F23 F 0.64639(19) 0.47473(15) 0.19513(15) 0.0910(7) Uani 1 1 d . . . . .
F24 F 0.58382(18) 0.5526(2) 0.31077(19) 0.1013(7) Uani 1 1 d . . . . .
F31 F 0.31427(14) 0.08689(14) 0.47591(10) 0.0563(4) Uani 1 1 d . . . . .
F32 F 0.34814(15) 0.14843(13) 0.34831(11) 0.0540(4) Uani 1 1 d . . . . .
F25A F 0.702(2) 0.6394(19) 0.1266(9) 0.109(4) Uani 0.43(3) 1 d . U P A 1
F26A F 0.6940(18) 0.7576(13) 0.2422(11) 0.086(3) Uani 0.43(3) 1 d . U P A 1
F27A F 0.5212(12) 0.6038(11) 0.1685(17) 0.099(4) Uani 0.43(3) 1 d . U P A 1
F33 F 0.1203(3) -0.1328(3) 0.3211(4) 0.0823(15) Uani 0.646(6) 1 d D U P B 1
F34 F 0.1645(3) -0.0357(4) 0.2147(2) 0.0662(11) Uani 0.646(6) 1 d D U P B 1
F35 F 0.1159(3) 0.1295(3) 0.3340(4) 0.0762(12) Uani 0.646(6) 1 d D U P B 1
F36 F -0.0415(4) -0.0491(7) 0.2640(4) 0.091(2) Uani 0.646(6) 1 d D U P B 1
F37 F 0.0523(5) 0.0152(6) 0.4219(4) 0.1088(17) Uani 0.646(6) 1 d D U P B 1
C29A C 0.1579(7) -0.0333(7) 0.3378(6) 0.047(2) Uani 0.354(6) 1 d D U P B 2
F25B F 0.7443(9) 0.6884(14) 0.1507(11) 0.109(3) Uani 0.57(3) 1 d . U P A 2
F26B F 0.6677(16) 0.7494(11) 0.2670(12) 0.110(4) Uani 0.57(3) 1 d . U P A 2
F27B F 0.5447(8) 0.5991(7) 0.1262(9) 0.080(2) Uani 0.57(3) 1 d . U P A 2
F33A F 0.1167(5) -0.1058(5) 0.3924(5) 0.0653(18) Uani 0.354(6) 1 d D U P B 2
F34A F 0.1300(5) -0.1034(6) 0.2437(4) 0.070(2) Uani 0.354(6) 1 d D U P B 2
F35A F 0.0821(8) 0.0758(10) 0.2639(9) 0.106(3) Uani 0.354(6) 1 d D U P B 2
F36A F -0.0544(7) -0.0557(11) 0.3052(8) 0.075(3) Uani 0.354(6) 1 d D U P B 2
F37A F 0.0925(8) 0.0942(8) 0.4170(6) 0.099(3) Uani 0.354(6) 1 d D U P B 2
O1 O 0.46325(15) 0.12557(15) 0.14800(12) 0.0455(4) Uani 1 1 d . . . . .
O2 O 0.86152(16) 0.47602(15) 0.33335(12) 0.0449(4) Uani 1 1 d . . . . .
O3 O 0.37829(18) -0.08289(17) 0.40587(14) 0.0576(5) Uani 1 1 d . . . . .
N1 N 0.70642(16) 0.21615(16) 0.14238(12) 0.0331(4) Uani 1 1 d . . . . .
H1 H 0.643221 0.184145 0.169163 0.040 Uiso 1 1 calc R U . . .
N2 N 0.81862(17) 0.37075(16) 0.47167(13) 0.0365(4) Uani 1 1 d . . . . .
H2 H 0.842039 0.382577 0.417390 0.044 Uiso 1 1 calc R U . . .
N3 N 0.45459(17) 0.01491(17) 0.29653(13) 0.0382(4) Uani 1 1 d . . . . .
H3 H 0.454042 0.068142 0.268866 0.068(9) Uiso 1 1 calc R . . . .
N4 N 0.74861(16) 0.13608(15) 0.32236(12) 0.0317(4) Uani 1 1 d . . . . .
C30 C 0.0700(3) 0.0202(3) 0.3329(2) 0.0617(7) Uani 1 1 d D U . . .
C1 C 0.7931(2) 0.1171(2) 0.23198(16) 0.0370(5) Uani 1 1 d . . . . .
H1A H 0.724792 0.043415 0.180345 0.044 Uiso 1 1 calc R U . . .
H1B H 0.870599 0.107355 0.249335 0.044 Uiso 1 1 calc R U . . .
C2 C 0.8258(2) 0.2181(2) 0.18820(16) 0.0366(5) Uani 1 1 d . . . . .
H2A H 0.882966 0.294010 0.242020 0.044 Uiso 1 1 calc R U . . .
H2B H 0.871875 0.209913 0.136955 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6682(2) 0.02338(19) 0.33765(17) 0.0389(5) Uani 1 1 d . . . . .
H3A H 0.666060 0.038671 0.408692 0.047 Uiso 1 1 calc R U . . .
H3B H 0.709002 -0.027496 0.325220 0.047 Uiso 1 1 calc R U . . .
C4 C 0.5313(2) -0.0419(2) 0.27057(18) 0.0421(5) Uani 1 1 d . . . . .
H4A H 0.533286 -0.048403 0.200024 0.051 Uiso 1 1 calc R U . . .
H4B H 0.488986 -0.122671 0.275121 0.051 Uiso 1 1 calc R U . . .
C5 C 0.8614(2) 0.2101(2) 0.41169(15) 0.0366(5) Uani 1 1 d . . . . .
H5A H 0.931507 0.268256 0.392049 0.044 Uiso 1 1 calc R U . . .
H5B H 0.893232 0.159606 0.435226 0.044 Uiso 1 1 calc R U . . .
C6 C 0.8315(2) 0.2749(2) 0.49748(16) 0.0376(5) Uani 1 1 d . . . . .
H6A H 0.750202 0.220394 0.508542 0.045 Uiso 1 1 calc R U . . .
H6B H 0.901960 0.306625 0.560112 0.045 Uiso 1 1 calc R U . . .
C7 C 0.67531(19) 0.25349(18) 0.06805(14) 0.0308(4) Uani 1 1 d . . . . .
C8 C 0.54540(19) 0.22736(19) 0.03512(15) 0.0318(5) Uani 1 1 d . . . . .
H8 H 0.521891 0.253450 -0.018239 0.038 Uiso 1 1 calc R U . . .
C9 C 0.4503(2) 0.16541(19) 0.07686(16) 0.0336(5) Uani 1 1 d . . . . .
C10 C 0.31234(19) 0.14323(19) 0.03241(16) 0.0342(5) Uani 1 1 d . . . . .
C11 C 0.2806(2) 0.2351(2) 0.08844(16) 0.0380(5) Uani 1 1 d . . . . .
C12 C 0.1397(3) 0.2095(3) 0.0580(2) 0.0563(7) Uani 1 1 d . . . . .
C13 C 0.7751(2) 0.3198(2) 0.01661(15) 0.0351(5) Uani 1 1 d . . . . .
C14 C 0.7234(2) 0.3783(2) -0.04789(18) 0.0483(6) Uani 1 1 d . . . . .
H14A H 0.647582 0.317522 -0.102676 0.072 Uiso 1 1 calc R U . . .
H14B H 0.790634 0.424581 -0.076111 0.072 Uiso 1 1 calc R U . . .
H14C H 0.698929 0.430252 -0.005980 0.072 Uiso 1 1 calc R U . . .
C15 C 0.8017(2) 0.2320(2) -0.05339(17) 0.0463(6) Uani 1 1 d . . . . .
H15A H 0.838963 0.196230 -0.013655 0.069 Uiso 1 1 calc R U . . .
H15B H 0.862557 0.273338 -0.088495 0.069 Uiso 1 1 calc R U . . .
H15C H 0.720652 0.170404 -0.102710 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9003(2) 0.4182(2) 0.09526(16) 0.0412(5) Uani 1 1 d . . . . .
H16A H 0.878932 0.461861 0.148120 0.062 Uiso 1 1 calc R U . . .
H16B H 0.953192 0.471866 0.062764 0.062 Uiso 1 1 calc R U . . .
H16C H 0.948671 0.383458 0.124988 0.062 Uiso 1 1 calc R U . . .
C17 C 0.7786(2) 0.44336(19) 0.51389(15) 0.0376(5) Uani 1 1 d . . . . .
C18 C 0.7807(2) 0.5283(2) 0.46843(17) 0.0411(5) Uani 1 1 d . . . . .
H18 H 0.754744 0.582903 0.498669 0.049 Uiso 1 1 calc R U . . .
C19 C 0.8191(2) 0.5361(2) 0.38112(17) 0.0387(5) Uani 1 1 d . . . . .
C20 C 0.8048(2) 0.6262(2) 0.33451(18) 0.0445(6) Uani 1 1 d . . . . .
C21 C 0.6726(3) 0.5763(2) 0.2604(2) 0.0524(6) Uani 1 1 d . . . . .
C22 C 0.6528(3) 0.6513(3) 0.1994(3) 0.0710(8) Uani 1 1 d . U . . .
C23 C 0.7252(2) 0.4327(2) 0.60508(16) 0.0430(6) Uani 1 1 d . . . . .
C24 C 0.5890(2) 0.3263(2) 0.5678(2) 0.0507(6) Uani 1 1 d . . . . .
H24A H 0.534240 0.338503 0.517495 0.076 Uiso 1 1 calc R U . . .
H24B H 0.552062 0.317551 0.624572 0.076 Uiso 1 1 calc R U . . .
H24C H 0.593752 0.254989 0.537431 0.076 Uiso 1 1 calc R U . . .
C25 C 0.8114(3) 0.4162(3) 0.68673(17) 0.0614(8) Uani 1 1 d . . . . .
H25A H 0.795017 0.334542 0.666767 0.092 Uiso 1 1 calc R U . . .
H25B H 0.791290 0.434494 0.750739 0.092 Uiso 1 1 calc R U . . .
H25C H 0.902421 0.469217 0.694503 0.092 Uiso 1 1 calc R U . . .
C26 C 0.7146(3) 0.5427(2) 0.6525(2) 0.0671(8) Uani 1 1 d . . . . .
H26A H 0.799770 0.612463 0.672399 0.101 Uiso 1 1 calc R U . . .
H26B H 0.683149 0.535066 0.711936 0.101 Uiso 1 1 calc R U . . .
H26C H 0.654099 0.550663 0.603538 0.101 Uiso 1 1 calc R U . . .
C27 C 0.3855(2) -0.0118(2) 0.36101(17) 0.0401(5) Uani 1 1 d . . . . .
C28 C 0.3046(2) 0.0506(2) 0.37718(16) 0.0401(5) Uani 1 1 d D . . . .
C29 C 0.1647(5) -0.0254(4) 0.3115(4) 0.0498(14) Uani 0.646(6) 1 d D U P B 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F11 C10 1.361(2) . ?
F12 C10 1.349(2) . ?
F13 C11 1.344(2) . ?
F14 C11 1.341(3) . ?
F15 C12 1.298(3) . ?
F16 C12 1.320(3) . ?
F17 C12 1.335(3) . ?
F21 C20 1.342(3) . ?
F22 C20 1.351(3) . ?
F23 C21 1.334(3) . ?
F24 C21 1.330(3) . ?
F31 C28 1.348(3) . ?
F32 C28 1.354(3) . ?
F25A C22 1.278(15) . ?
F26A C22 1.241(15) . ?
F27A C22 1.370(12) . ?
F33 C29 1.335(6) . ?
F34 C29 1.349(6) . ?
F35 C30 1.306(4) . ?
F36 C30 1.318(5) . ?
F37 C30 1.322(5) . ?
C29A F33A 1.340(8) . ?
C29A F34A 1.348(8) . ?
C29A C30 1.499(11) . ?
C29A C28 1.541(7) . ?
F25B C22 1.351(10) . ?
F26B C22 1.361(12) . ?
F27B C22 1.317(7) . ?
F35A C30 1.335(6) . ?
F36A C30 1.319(7) . ?
F37A C30 1.277(6) . ?
O1 C9 1.254(2) . ?
O2 C19 1.252(3) . ?
O3 C27 1.226(3) . ?
N1 H1 0.8800 . ?
N1 C2 1.461(3) . ?
N1 C7 1.326(3) . ?
N2 H2 0.8800 . ?
N2 C6 1.458(3) . ?
N2 C17 1.322(3) . ?
N3 H3 0.8800 . ?
N3 C4 1.455(3) . ?
N3 C27 1.326(3) . ?
N4 C1 1.473(3) . ?
N4 C3 1.473(3) . ?
N4 C5 1.479(3) . ?
C30 C29 1.531(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.521(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.513(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.411(3) . ?
C7 C13 1.537(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(3) . ?
C9 C10 1.544(3) . ?
C10 C11 1.526(3) . ?
C11 C12 1.535(3) . ?
C13 C14 1.539(3) . ?
C13 C15 1.535(3) . ?
C13 C16 1.539(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.407(3) . ?
C17 C23 1.532(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.393(3) . ?
C19 C20 1.540(3) . ?
C20 C21 1.527(4) . ?
C21 C22 1.517(4) . ?
C23 C24 1.535(3) . ?
C23 C25 1.544(4) . ?
C23 C26 1.535(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.531(3) . ?
C28 C29 1.531(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F33A C29A F34A 105.8(7) . . ?
F33A C29A C30 104.9(6) . . ?
F33A C29A C28 112.0(6) . . ?
F34A C29A C30 106.1(6) . . ?
F34A C29A C28 109.3(6) . . ?
C30 C29A C28 117.9(6) . . ?
C2 N1 H1 113.9 . . ?
C7 N1 H1 113.9 . . ?
C7 N1 C2 132.12(18) . . ?
C6 N2 H2 113.7 . . ?
C17 N2 H2 113.7 . . ?
C17 N2 C6 132.53(19) . . ?
C4 N3 H3 119.3 . . ?
C27 N3 H3 119.3 . . ?
C27 N3 C4 121.4(2) . . ?
C1 N4 C3 111.06(17) . . ?
C1 N4 C5 109.65(16) . . ?
C3 N4 C5 109.04(16) . . ?
F35 C30 F36 111.7(5) . . ?
F35 C30 F37 108.3(4) . . ?
F35 C30 C29 110.6(3) . . ?
F36 C30 F37 108.5(4) . . ?
F36 C30 C29 108.4(5) . . ?
F37 C30 C29 109.3(4) . . ?
F35A C30 C29A 111.6(5) . . ?
F36A C30 C29A 115.1(8) . . ?
F36A C30 F35A 103.1(7) . . ?
F37A C30 C29A 112.1(5) . . ?
F37A C30 F35A 107.7(7) . . ?
F37A C30 F36A 106.6(7) . . ?
N4 C1 H1A 109.1 . . ?
N4 C1 H1B 109.1 . . ?
N4 C1 C2 112.70(17) . . ?
H1A C1 H1B 107.8 . . ?
C2 C1 H1A 109.1 . . ?
C2 C1 H1B 109.1 . . ?
N1 C2 C1 109.06(17) . . ?
N1 C2 H2A 109.9 . . ?
N1 C2 H2B 109.9 . . ?
C1 C2 H2A 109.9 . . ?
C1 C2 H2B 109.9 . . ?
H2A C2 H2B 108.3 . . ?
N4 C3 H3A 108.8 . . ?
N4 C3 H3B 108.8 . . ?
N4 C3 C4 113.78(18) . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
N3 C4 C3 113.20(19) . . ?
N3 C4 H4A 108.9 . . ?
N3 C4 H4B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.8 . . ?
N4 C5 H5A 108.9 . . ?
N4 C5 H5B 108.9 . . ?
N4 C5 C6 113.23(17) . . ?
H5A C5 H5B 107.7 . . ?
C6 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N2 C6 C5 108.41(17) . . ?
N2 C6 H6A 110.0 . . ?
N2 C6 H6B 110.0 . . ?
C5 C6 H6A 110.0 . . ?
C5 C6 H6B 110.0 . . ?
H6A C6 H6B 108.4 . . ?
N1 C7 C8 117.64(18) . . ?
N1 C7 C13 121.84(18) . . ?
C8 C7 C13 120.50(18) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 C7 123.20(19) . . ?
C9 C8 H8 118.4 . . ?
O1 C9 C8 127.47(19) . . ?
O1 C9 C10 115.37(18) . . ?
C8 C9 C10 117.16(18) . . ?
F11 C10 C9 111.36(17) . . ?
F11 C10 C11 106.89(17) . . ?
F12 C10 F11 106.40(17) . . ?
F12 C10 C9 109.73(17) . . ?
F12 C10 C11 108.12(17) . . ?
C11 C10 C9 114.00(18) . . ?
F13 C11 C10 109.38(18) . . ?
F13 C11 C12 107.18(19) . . ?
F14 C11 F13 108.05(18) . . ?
F14 C11 C10 108.36(17) . . ?
F14 C11 C12 106.7(2) . . ?
C10 C11 C12 116.82(19) . . ?
F15 C12 F16 109.1(2) . . ?
F15 C12 F17 107.3(2) . . ?
F15 C12 C11 112.7(2) . . ?
F16 C12 F17 106.5(2) . . ?
F16 C12 C11 110.7(2) . . ?
F17 C12 C11 110.4(2) . . ?
C7 C13 C14 110.86(17) . . ?
C7 C13 C16 110.76(17) . . ?
C14 C13 C16 107.2(2) . . ?
C15 C13 C7 109.19(18) . . ?
C15 C13 C14 107.75(18) . . ?
C15 C13 C16 111.05(18) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 C18 117.1(2) . . ?
N2 C17 C23 122.1(2) . . ?
C18 C17 C23 120.7(2) . . ?
C17 C18 H18 118.5 . . ?
C19 C18 C17 123.0(2) . . ?
C19 C18 H18 118.5 . . ?
O2 C19 C18 127.7(2) . . ?
O2 C19 C20 115.0(2) . . ?
C18 C19 C20 117.3(2) . . ?
F21 C20 F22 106.7(2) . . ?
F21 C20 C19 111.81(19) . . ?
F21 C20 C21 108.3(2) . . ?
F22 C20 C19 109.4(2) . . ?
F22 C20 C21 107.1(2) . . ?
C21 C20 C19 113.2(2) . . ?
F23 C21 C20 108.4(2) . . ?
F23 C21 C22 107.1(3) . . ?
F24 C21 F23 107.5(2) . . ?
F24 C21 C20 108.6(2) . . ?
F24 C21 C22 106.8(2) . . ?
C22 C21 C20 118.0(2) . . ?
F25A C22 F27A 113.0(8) . . ?
F25A C22 C21 106.8(8) . . ?
F26A C22 F25A 109.3(10) . . ?
F26A C22 F27A 105.3(10) . . ?
F26A C22 C21 119.0(8) . . ?
F27A C22 C21 103.5(8) . . ?
F25B C22 F26B 106.5(7) . . ?
F25B C22 C21 112.1(6) . . ?
F26B C22 C21 106.1(7) . . ?
F27B C22 F25B 102.7(5) . . ?
F27B C22 F26B 112.9(8) . . ?
F27B C22 C21 116.2(5) . . ?
C17 C23 C24 107.61(18) . . ?
C17 C23 C25 111.9(2) . . ?
C17 C23 C26 110.9(2) . . ?
C24 C23 C25 110.0(2) . . ?
C26 C23 C24 108.2(2) . . ?
C26 C23 C25 108.2(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O3 C27 N3 126.4(2) . . ?
O3 C27 C28 118.0(2) . . ?
N3 C27 C28 115.54(19) . . ?
F31 C28 F32 106.34(19) . . ?
F31 C28 C29A 99.0(4) . . ?
F31 C28 C27 109.64(18) . . ?
F31 C28 C29 113.2(3) . . ?
F32 C28 C29A 115.7(4) . . ?
F32 C28 C27 111.59(18) . . ?
F32 C28 C29 103.8(3) . . ?
C27 C28 C29A 113.4(4) . . ?
C27 C28 C29 112.0(3) . . ?
F33 C29 F34 107.8(4) . . ?
F33 C29 C30 108.6(4) . . ?
F33 C29 C28 108.4(4) . . ?
F34 C29 C30 107.2(4) . . ?
F34 C29 C28 108.2(4) . . ?
C28 C29 C30 116.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F11 C10 C11 F13 -173.15(17) . . . . ?
F11 C10 C11 F14 -55.6(2) . . . . ?
F11 C10 C11 C12 64.9(3) . . . . ?
F12 C10 C11 F13 72.7(2) . . . . ?
F12 C10 C11 F14 -169.77(17) . . . . ?
F12 C10 C11 C12 -49.3(3) . . . . ?
F13 C11 C12 F15 -171.2(2) . . . . ?
F13 C11 C12 F16 66.4(3) . . . . ?
F13 C11 C12 F17 -51.3(3) . . . . ?
F14 C11 C12 F15 73.2(3) . . . . ?
F14 C11 C12 F16 -49.2(3) . . . . ?
F14 C11 C12 F17 -166.9(2) . . . . ?
F21 C20 C21 F23 -174.8(2) . . . . ?
F21 C20 C21 F24 -58.3(3) . . . . ?
F21 C20 C21 C22 63.3(3) . . . . ?
F22 C20 C21 F23 70.5(3) . . . . ?
F22 C20 C21 F24 -173.0(2) . . . . ?
F22 C20 C21 C22 -51.4(3) . . . . ?
F23 C21 C22 F25A -42.4(11) . . . . ?
F23 C21 C22 F26A -166.7(11) . . . . ?
F23 C21 C22 F27A 77.0(10) . . . . ?
F23 C21 C22 F25B -69.8(9) . . . . ?
F23 C21 C22 F26B 174.3(8) . . . . ?
F23 C21 C22 F27B 47.8(8) . . . . ?
F24 C21 C22 F25A -157.3(11) . . . . ?
F24 C21 C22 F26A 78.5(11) . . . . ?
F24 C21 C22 F27A -37.8(10) . . . . ?
F24 C21 C22 F25B 175.3(8) . . . . ?
F24 C21 C22 F26B 59.4(9) . . . . ?
F24 C21 C22 F27B -67.1(8) . . . . ?
F31 C28 C29 F33 -76.2(5) . . . . ?
F31 C28 C29 F34 167.1(3) . . . . ?
F31 C28 C29 C30 46.4(5) . . . . ?
F32 C28 C29 F33 168.9(4) . . . . ?
F32 C28 C29 F34 52.3(4) . . . . ?
F32 C28 C29 C30 -68.4(4) . . . . ?
F35 C30 C29 F33 173.8(4) . . . . ?
F35 C30 C29 F34 -70.0(5) . . . . ?
F35 C30 C29 C28 51.3(5) . . . . ?
F36 C30 C29 F33 -63.4(6) . . . . ?
F36 C30 C29 F34 52.7(6) . . . . ?
F36 C30 C29 C28 174.0(5) . . . . ?
F37 C30 C29 F33 54.6(5) . . . . ?
F37 C30 C29 F34 170.8(4) . . . . ?
F37 C30 C29 C28 -68.0(5) . . . . ?
F33A C29A C30 F35A -167.2(7) . . . . ?
F33A C29A C30 F36A -50.1(8) . . . . ?
F33A C29A C30 F37A 72.0(8) . . . . ?
F33A C29A C28 F31 -47.3(8) . . . . ?
F33A C29A C28 F32 -160.4(6) . . . . ?
F33A C29A C28 C27 68.8(8) . . . . ?
F34A C29A C30 F35A -55.4(8) . . . . ?
F34A C29A C30 F36A 61.6(8) . . . . ?
F34A C29A C30 F37A -176.3(7) . . . . ?
F34A C29A C28 F31 -164.2(6) . . . . ?
F34A C29A C28 F32 82.6(7) . . . . ?
F34A C29A C28 C27 -48.2(7) . . . . ?
O1 C9 C10 F11 -153.70(19) . . . . ?
O1 C9 C10 F12 -36.2(3) . . . . ?
O1 C9 C10 C11 85.3(2) . . . . ?
O2 C19 C20 F21 -147.4(2) . . . . ?
O2 C19 C20 F22 -29.4(3) . . . . ?
O2 C19 C20 C21 90.0(3) . . . . ?
O3 C27 C28 F31 44.6(3) . . . . ?
O3 C27 C28 F32 162.1(2) . . . . ?
O3 C27 C28 C29A -65.0(4) . . . . ?
O3 C27 C28 C29 -81.9(3) . . . . ?
N1 C7 C8 C9 0.2(3) . . . . ?
N1 C7 C13 C14 -166.3(2) . . . . ?
N1 C7 C13 C15 75.1(2) . . . . ?
N1 C7 C13 C16 -47.5(3) . . . . ?
N2 C17 C18 C19 1.8(3) . . . . ?
N2 C17 C23 C24 -74.4(3) . . . . ?
N2 C17 C23 C25 46.5(3) . . . . ?
N2 C17 C23 C26 167.4(2) . . . . ?
N3 C27 C28 F31 -137.2(2) . . . . ?
N3 C27 C28 F32 -19.6(3) . . . . ?
N3 C27 C28 C29A 113.2(4) . . . . ?
N3 C27 C28 C29 96.3(3) . . . . ?
N4 C1 C2 N1 -71.2(2) . . . . ?
N4 C3 C4 N3 -69.9(3) . . . . ?
N4 C5 C6 N2 -73.7(2) . . . . ?
C30 C29A C28 F31 74.5(6) . . . . ?
C30 C29A C28 F32 -38.6(7) . . . . ?
C30 C29A C28 C27 -169.4(5) . . . . ?
C1 N4 C3 C4 -78.5(2) . . . . ?
C1 N4 C5 C6 156.40(18) . . . . ?
C2 N1 C7 C8 173.8(2) . . . . ?
C2 N1 C7 C13 -4.4(3) . . . . ?
C3 N4 C1 C2 155.98(17) . . . . ?
C3 N4 C5 C6 -81.8(2) . . . . ?
C4 N3 C27 O3 0.9(4) . . . . ?
C4 N3 C27 C28 -177.17(19) . . . . ?
C5 N4 C1 C2 -83.5(2) . . . . ?
C5 N4 C3 C4 160.57(18) . . . . ?
C6 N2 C17 C18 179.1(2) . . . . ?
C6 N2 C17 C23 -4.1(4) . . . . ?
C7 N1 C2 C1 -153.0(2) . . . . ?
C7 C8 C9 O1 1.0(4) . . . . ?
C7 C8 C9 C10 -179.75(19) . . . . ?
C8 C7 C13 C14 15.5(3) . . . . ?
C8 C7 C13 C15 -103.0(2) . . . . ?
C8 C7 C13 C16 134.4(2) . . . . ?
C8 C9 C10 F11 26.9(3) . . . . ?
C8 C9 C10 F12 144.47(19) . . . . ?
C8 C9 C10 C11 -94.1(2) . . . . ?
C9 C10 C11 F13 -49.7(2) . . . . ?
C9 C10 C11 F14 67.9(2) . . . . ?
C9 C10 C11 C12 -171.6(2) . . . . ?
C10 C11 C12 F15 -48.2(3) . . . . ?
C10 C11 C12 F16 -170.6(2) . . . . ?
C10 C11 C12 F17 71.8(3) . . . . ?
C13 C7 C8 C9 178.4(2) . . . . ?
C17 N2 C6 C5 170.7(2) . . . . ?
C17 C18 C19 O2 -3.4(4) . . . . ?
C17 C18 C19 C20 174.6(2) . . . . ?
C18 C17 C23 C24 102.3(2) . . . . ?
C18 C17 C23 C25 -136.8(2) . . . . ?
C18 C17 C23 C26 -15.9(3) . . . . ?
C18 C19 C20 F21 34.4(3) . . . . ?
C18 C19 C20 F22 152.3(2) . . . . ?
C18 C19 C20 C21 -88.3(3) . . . . ?
C19 C20 C21 F23 -50.3(3) . . . . ?
C19 C20 C21 F24 66.2(3) . . . . ?
C19 C20 C21 C22 -172.1(3) . . . . ?
C20 C21 C22 F25A 80.1(11) . . . . ?
C20 C21 C22 F26A -44.1(11) . . . . ?
C20 C21 C22 F27A -160.4(10) . . . . ?
C20 C21 C22 F25B 52.7(9) . . . . ?
C20 C21 C22 F26B -63.2(9) . . . . ?
C20 C21 C22 F27B 170.3(8) . . . . ?
C23 C17 C18 C19 -175.1(2) . . . . ?
C27 N3 C4 C3 -90.9(3) . . . . ?
C27 C28 C29 F33 48.3(5) . . . . ?
C27 C28 C29 F34 -68.3(4) . . . . ?
C27 C28 C29 C30 171.0(3) . . . . ?
C28 C29A C30 F35A 67.4(8) . . . . ?
C28 C29A C30 F36A -175.5(6) . . . . ?
C28 C29A C30 F37A -53.4(9) . . . . ?

_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_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_dal23_41
_database_code_depnum_ccdc_archive 'CCDC 2313986'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-12-10
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H23 F9 N4 O3'
_chemical_formula_sum            'C18 H23 F9 N4 O3'
_chemical_formula_weight         514.40
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.6050(6)
_cell_length_b                   10.3650(7)
_cell_length_c                   12.3331(8)
_cell_angle_alpha                73.689(2)
_cell_angle_beta                 71.252(2)
_cell_angle_gamma                89.295(2)
_cell_volume                     1111.78(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7490
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      27.044
_cell_measurement_theta_min      2.314
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.969
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1200 before and 0.0595 after correction.
The Ratio of minimum to maximum transmission is 0.9348.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.206
_exptl_crystal_size_mid          0.184
_exptl_crystal_size_min          0.052
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0665
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            45208
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.281
_diffrn_reflns_theta_min         2.055
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 Venture Duo with Photon 3'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3955
_reflns_number_total             5506
_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       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.354
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0067(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         5506
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0437
_refine_ls_restrained_S_all      1.030
_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)+(0.0451P)²+0.4845P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1172
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C18-F7A = C18-F8A = C18-F9A = C18-F7B = C18-F8B = C18-F9B
 1.32273 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C18 \\sim F7A \\sim F8A \\sim F9A \\sim F7B \\sim F8B \\sim F9B: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 F7A, F8A, F9A, F7B, F8B, F9B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Sof(F7B)=Sof(F8B)=Sof(F9B)=1-FVAR(1)
 Sof(F7A)=Sof(F8A)=Sof(F9A)=FVAR(1)
6.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C15(H15A,H15B), C16(H16A,
 H16B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), N3(H3), C4(H4), C11(H11)
6.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_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
F1 F 0.76556(11) 0.41823(13) 0.23938(10) 0.0469(3) Uani 1 1 d . . . . .
F2 F 0.67023(13) 0.21640(12) 0.34052(11) 0.0455(3) Uani 1 1 d . . . . .
F3 F 0.64029(12) 0.37271(12) 0.42735(10) 0.0424(3) Uani 1 1 d . . . . .
F4 F 0.34234(14) 0.22973(14) 0.65774(12) 0.0543(3) Uani 1 1 d . . . . .
F5 F 0.18607(16) 0.37510(12) 0.64006(12) 0.0557(3) Uani 1 1 d . . . . .
F6 F 0.11286(16) 0.17614(15) 0.75618(10) 0.0629(4) Uani 1 1 d . . . . .
O1 O 0.49582(13) 0.32626(13) 0.21370(11) 0.0331(3) Uani 1 1 d . . . . .
O2 O 0.08050(14) 0.25521(13) 0.51462(11) 0.0363(3) Uani 1 1 d . . . . .
O3 O 0.63915(17) 0.12408(16) -0.11671(13) 0.0516(4) Uani 1 1 d . . . . .
N1 N 0.25311(15) 0.45251(14) 0.23377(12) 0.0281(3) Uani 1 1 d . . . . .
H1 H 0.319144 0.405374 0.197435 0.034 Uiso 1 1 calc R U . . .
N2 N 0.15297(15) 0.10129(15) 0.36789(12) 0.0290(3) Uani 1 1 d . . . . .
H2 H 0.099547 0.162956 0.393694 0.035 Uiso 1 1 calc R U . . .
N3 N 0.52547(16) 0.24797(15) 0.00731(13) 0.0312(3) Uani 1 1 d . . . . .
H3 H 0.520680 0.267480 0.073345 0.037 Uiso 1 1 calc R U . . .
N4 N 0.19057(15) 0.27763(14) 0.11832(12) 0.0282(3) Uani 1 1 d . . . . .
C1 C 0.1417(2) 0.41447(19) 0.09472(16) 0.0346(4) Uani 1 1 d . . . . .
H1A H 0.047821 0.413167 0.077750 0.042 Uiso 1 1 calc R U . . .
H1B H 0.216321 0.475052 0.023162 0.042 Uiso 1 1 calc R U . . .
C2 C 0.1195(2) 0.46865(19) 0.20139(17) 0.0347(4) Uani 1 1 d . . . . .
H2A H 0.100635 0.565110 0.180030 0.042 Uiso 1 1 calc R U . . .
H2B H 0.033716 0.418056 0.269741 0.042 Uiso 1 1 calc R U . . .
C3 C 0.28597(18) 0.50079(16) 0.31155(14) 0.0259(3) Uani 1 1 d . . . . .
C4 C 0.41383(17) 0.46463(16) 0.34155(14) 0.0255(3) Uani 1 1 d . . . . .
H4 H 0.435978 0.499433 0.398196 0.031 Uiso 1 1 calc R U . . .
C5 C 0.50805(17) 0.37940(17) 0.29027(14) 0.0260(3) Uani 1 1 d . . . . .
C6 C 0.64563(19) 0.34639(19) 0.32599(16) 0.0322(4) Uani 1 1 d . . . . .
C7 C 0.1865(2) 0.59399(18) 0.36591(16) 0.0329(4) Uani 1 1 d . . . . .
H7A H 0.192568 0.679449 0.304285 0.049 Uiso 1 1 calc R U . . .
H7B H 0.216904 0.610937 0.429653 0.049 Uiso 1 1 calc R U . . .
H7C H 0.084711 0.552811 0.399524 0.049 Uiso 1 1 calc R U . . .
C8 C 0.06818(18) 0.17534(19) 0.19638(16) 0.0339(4) Uani 1 1 d . . . . .
H8A H 0.023718 0.141483 0.146392 0.041 Uiso 1 1 calc R U . . .
H8B H -0.008804 0.217353 0.247465 0.041 Uiso 1 1 calc R U . . .
C9 C 0.1194(2) 0.05828(18) 0.27504(15) 0.0328(4) Uani 1 1 d . . . . .
H9A H 0.041242 -0.017385 0.312651 0.039 Uiso 1 1 calc R U . . .
H9B H 0.208556 0.026524 0.225929 0.039 Uiso 1 1 calc R U . . .
C10 C 0.25424(18) 0.05788(16) 0.41701(15) 0.0282(3) Uani 1 1 d . . . . .
C11 C 0.27061(19) 0.10715(17) 0.50780(15) 0.0290(3) Uani 1 1 d . . . . .
H11 H 0.344092 0.074058 0.542343 0.035 Uiso 1 1 calc R U . . .
C12 C 0.18287(18) 0.20267(16) 0.54871(15) 0.0285(3) Uani 1 1 d . . . . .
C13 C 0.2076(2) 0.24560(18) 0.65087(16) 0.0343(4) Uani 1 1 d . . . . .
C14 C 0.3505(2) -0.0441(2) 0.3742(2) 0.0467(5) Uani 1 1 d . . . . .
H14A H 0.289051 -0.124528 0.385074 0.070 Uiso 1 1 calc R U . . .
H14B H 0.417993 -0.068793 0.420312 0.070 Uiso 1 1 calc R U . . .
H14C H 0.407612 -0.005813 0.289169 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2665(2) 0.24274(19) 0.00726(15) 0.0326(4) Uani 1 1 d . . . . .
H15A H 0.209742 0.272194 -0.048379 0.039 Uiso 1 1 calc R U . . .
H15B H 0.267138 0.143403 0.026433 0.039 Uiso 1 1 calc R U . . .
C16 C 0.4232(2) 0.30519(19) -0.05530(15) 0.0348(4) Uani 1 1 d . . . . .
H16A H 0.458439 0.293591 -0.136472 0.042 Uiso 1 1 calc R U . . .
H16B H 0.424159 0.403240 -0.064609 0.042 Uiso 1 1 calc R U . . .
C17 C 0.6255(2) 0.16749(18) -0.03199(15) 0.0331(4) Uani 1 1 d . . . . .
C18 C 0.7336(2) 0.1306(2) 0.03805(18) 0.0391(4) Uani 1 1 d D U . . .
F7A F 0.6679(9) 0.0624(13) 0.1550(9) 0.0628(19) Uani 0.54(3) 1 d D U P A 1
F8A F 0.7796(9) 0.2309(9) 0.0656(11) 0.0658(19) Uani 0.54(3) 1 d D U P A 1
F9A F 0.8442(8) 0.0689(13) -0.0118(11) 0.0587(19) Uani 0.54(3) 1 d D U P A 1
F7B F 0.6769(11) 0.0236(17) 0.1280(12) 0.066(3) Uani 0.46(3) 1 d D U P A 2
F8B F 0.7969(12) 0.2439(7) 0.0430(11) 0.065(2) Uani 0.46(3) 1 d D U P A 2
F9B F 0.8513(11) 0.0895(17) -0.0300(13) 0.072(3) Uani 0.46(3) 1 d D U P A 2


_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
F1 C6 1.344(2) . ?
F2 C6 1.337(2) . ?
F3 C6 1.3378(19) . ?
F4 C13 1.329(2) . ?
F5 C13 1.331(2) . ?
F6 C13 1.328(2) . ?
O1 C5 1.2547(19) . ?
O2 C12 1.251(2) . ?
O3 C17 1.219(2) . ?
N1 H1 0.8800 . ?
N1 C2 1.457(2) . ?
N1 C3 1.318(2) . ?
N2 H2 0.8800 . ?
N2 C9 1.463(2) . ?
N2 C10 1.316(2) . ?
N3 H3 0.8800 . ?
N3 C16 1.459(2) . ?
N3 C17 1.327(2) . ?
N4 C1 1.468(2) . ?
N4 C8 1.471(2) . ?
N4 C15 1.473(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C1 C2 1.524(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.410(2) . ?
C3 C7 1.492(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(2) . ?
C5 C6 1.528(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.512(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.405(2) . ?
C10 C14 1.492(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(2) . ?
C12 C13 1.534(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.509(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.533(3) . ?
C18 F7A 1.353(8) . ?
C18 F8A 1.304(7) . ?
C18 F9A 1.304(7) . ?
C18 F7B 1.301(9) . ?
C18 F8B 1.355(7) . ?
C18 F9B 1.320(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
F8Bb C18 C17 110.1(4) . . ?
C2 N1 H1 116.4 . . ?
C3 N1 H1 116.4 . . ?
C3 N1 C2 127.12(14) . . ?
F8Aa C18 C17 114.1(4) . . ?
F9Aa C18 C17 113.7(4) . . ?
F9Bb C18 C17 107.9(6) . . ?
F7Aa C18 C17 113.7(4) . . ?
C9 N2 H2 116.4 . . ?
C10 N2 H2 116.4 . . ?
C10 N2 C9 127.14(15) . . ?
C16 N3 H3 118.9 . . ?
C17 N3 H3 118.9 . . ?
C17 N3 C16 122.21(15) . . ?
C1 N4 C8 112.08(14) . . ?
C1 N4 C15 112.27(14) . . ?
F7Bb C18 C17 108.6(5) . . ?
F9Aa C18 F7A 110.9(6) . . ?
F8Aa C18 F7A 91.5(12) . . ?
F8Aa C18 F9A 110.9(5) . . ?
F9Bb C18 F8B 98.9(9) . . ?
F7Bb C18 F8B 125.8(13) . . ?
F7Bb C18 F9B 103.8(9) . . ?
C8 N4 C15 110.08(14) . . ?
N4 C1 H1A 109.4 . . ?
N4 C1 H1B 109.4 . . ?
N4 C1 C2 111.11(14) . . ?
H1A C1 H1B 108.0 . . ?
C2 C1 H1A 109.4 . . ?
C2 C1 H1B 109.4 . . ?
N1 C2 C1 107.93(14) . . ?
N1 C2 H2A 110.1 . . ?
N1 C2 H2B 110.1 . . ?
C1 C2 H2A 110.1 . . ?
C1 C2 H2B 110.1 . . ?
H2A C2 H2B 108.4 . . ?
N1 C3 C4 119.95(14) . . ?
N1 C3 C7 118.92(15) . . ?
C4 C3 C7 121.13(15) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 C3 121.55(14) . . ?
C5 C4 H4 119.2 . . ?
O1 C5 C4 127.26(15) . . ?
O1 C5 C6 114.21(14) . . ?
C4 C5 C6 118.51(14) . . ?
F1 C6 C5 110.17(14) . . ?
F2 C6 F1 106.58(14) . . ?
F2 C6 F3 106.95(14) . . ?
F2 C6 C5 111.68(14) . . ?
F3 C6 F1 107.07(14) . . ?
F3 C6 C5 114.00(14) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N4 C8 H8A 109.3 . . ?
N4 C8 H8B 109.3 . . ?
N4 C8 C9 111.69(14) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
N2 C9 C8 109.52(14) . . ?
N2 C9 H9A 109.8 . . ?
N2 C9 H9B 109.8 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
H9A C9 H9B 108.2 . . ?
N2 C10 C11 120.30(15) . . ?
N2 C10 C14 118.59(16) . . ?
C11 C10 C14 121.11(16) . . ?
C10 C11 H11 118.9 . . ?
C12 C11 C10 122.19(15) . . ?
C12 C11 H11 118.9 . . ?
O2 C12 C11 127.27(16) . . ?
O2 C12 C13 115.15(15) . . ?
C11 C12 C13 117.52(15) . . ?
F4 C13 F5 106.46(15) . . ?
F4 C13 C12 114.05(14) . . ?
F5 C13 C12 111.46(15) . . ?
F6 C13 F4 107.16(16) . . ?
F6 C13 F5 106.26(15) . . ?
F6 C13 C12 111.01(14) . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N4 C15 H15A 108.7 . . ?
N4 C15 H15B 108.7 . . ?
N4 C15 C16 114.05(14) . . ?
H15A C15 H15B 107.6 . . ?
C16 C15 H15A 108.7 . . ?
C16 C15 H15B 108.7 . . ?
N3 C16 C15 113.97(15) . . ?
N3 C16 H16A 108.8 . . ?
N3 C16 H16B 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
O3 C17 N3 126.57(18) . . ?
O3 C17 C18 119.13(17) . . ?
N3 C17 C18 114.30(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 F1 75.91(18) . . . . ?
O1 C5 C6 F2 -42.3(2) . . . . ?
O1 C5 C6 F3 -163.69(15) . . . . ?
O2 C12 C13 F4 -157.39(16) . . . . ?
O2 C12 C13 F5 -36.8(2) . . . . ?
O2 C12 C13 F6 81.4(2) . . . . ?
N1 C3 C4 C5 0.5(2) . . . . ?
N2 C10 C11 C12 -0.3(3) . . . . ?
N4 C1 C2 N1 51.7(2) . . . . ?
N4 C8 C9 N2 72.11(18) . . . . ?
N4 C15 C16 N3 70.7(2) . . . . ?
C1 N4 C8 C9 -147.76(14) . . . . ?
C1 N4 C15 C16 77.16(18) . . . . ?
C2 N1 C3 C4 173.64(16) . . . . ?
C2 N1 C3 C7 -6.7(3) . . . . ?
C3 N1 C2 C1 171.31(16) . . . . ?
C3 C4 C5 O1 0.8(3) . . . . ?
C3 C4 C5 C6 179.16(15) . . . . ?
C4 C5 C6 F1 -102.65(17) . . . . ?
C4 C5 C6 F2 139.11(16) . . . . ?
C4 C5 C6 F3 17.7(2) . . . . ?
C7 C3 C4 C5 -179.15(16) . . . . ?
C8 N4 C1 C2 77.57(18) . . . . ?
C8 N4 C15 C16 -157.24(14) . . . . ?
C9 N2 C10 C11 -178.46(16) . . . . ?
C9 N2 C10 C14 1.6(3) . . . . ?
C10 N2 C9 C8 -147.73(17) . . . . ?
C10 C11 C12 O2 1.0(3) . . . . ?
O3 C17 C18 F8Aa 137.4(6) . . . . ?
O3 C17 C18 F8Bb 125.7(6) . . . . ?
O3 C17 C18 F7Aa -119.4(8) . . . . ?
O3 C17 C18 F9Aa 8.8(7) . . . . ?
O3 C17 C18 F9Bb 18.8(8) . . . . ?
O3 C17 C18 F7Bb -93.0(11) . . . . ?
N3 C17 C18 F7Bb 88.0(11) . . . . ?
N3 C17 C18 F8Bb -53.2(6) . . . . ?
N3 C17 C18 F7Aa 61.6(8) . . . . ?
N3 C17 C18 F9Aa -170.2(7) . . . . ?
N3 C17 C18 F9Bb -160.1(8) . . . . ?
N3 C17 C18 F8Aa -41.6(6) . . . . ?
C10 C11 C12 C13 178.14(15) . . . . ?
C11 C12 C13 F4 25.2(2) . . . . ?
C11 C12 C13 F5 145.75(16) . . . . ?
C11 C12 C13 F6 -96.00(19) . . . . ?
C14 C10 C11 C12 179.63(18) . . . . ?
C15 N4 C1 C2 -157.93(15) . . . . ?
C15 N4 C8 C9 86.54(17) . . . . ?
C16 N3 C17 O3 -5.3(3) . . . . ?
C16 N3 C17 C18 173.53(15) . . . . ?
C17 N3 C16 C15 107.22(19) . . . . ?

_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_dal2127
_database_code_depnum_ccdc_archive 'CCDC 2313987'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H14 F30 N4 O3 Yb'
_chemical_formula_sum            'C27 H14 F30 N4 O3 Yb'
_chemical_formula_weight         1185.46
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   10.0912(10)
_cell_length_b                   10.4385(10)
_cell_length_c                   17.6508(18)
_cell_angle_alpha                89.530(5)
_cell_angle_beta                 86.742(5)
_cell_angle_gamma                86.666(5)
_cell_volume                     1853.1(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9924
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.42
_cell_measurement_theta_min      2.312
_shelx_estimated_absorpt_T_max   0.812
_shelx_estimated_absorpt_T_min   0.678
_exptl_absorpt_coefficient_mu    2.713
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0574 before and 0.0397 after correction.
The Ratio of minimum to maximum transmission is 0.9069.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_diffrn    2.125
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism-like
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          0.155
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            56905
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.464
_diffrn_reflns_theta_min         2.025
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex'
_diffrn_measurement_method       'CCD Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7419
_reflns_number_total             7590
_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       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.615
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     652
_refine_ls_number_reflns         7590
_refine_ls_number_restraints     317
_refine_ls_R_factor_all          0.0298
_refine_ls_R_factor_gt           0.0292
_refine_ls_restrained_S_all      1.123
_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)+(0.0390P)²+4.5250P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0769
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C36-F31A = C36-F31B = C36-F32A = C36-F32B = C37-F33A = C37-F33B = C37-F34A =
 C37-F34B
 1.36522 with sigma of 0.02
 C38-F35A = C38-F36A = C38-F37A = C38-F35B = C38-F36B = C38-F37B
 1.33054 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F31A \\sim F32A \\sim F33A \\sim F34A \\sim F35A \\sim F36A \\sim F37A \\sim
F31B \\sim F32B \\sim F33B \\sim F34B \\sim F35B \\sim F36B \\sim F37B \\sim
C36 \\sim C37 \\sim C38: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
4. Rigid body (RIGU) restrains
 F31A, F32A, F33A, F34A, F35A, F36A, F37A, F31B, F32B, F33B, F34B, F35B, F36B,
 F37B, C36, C37, C38
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(F31B)=Sof(F32B)=Sof(F33B)=Sof(F34B)=Sof(F35B)=Sof(F36B)=Sof(F37B)=1-FVAR(1)
 Sof(F31A)=Sof(F32A)=Sof(F33A)=Sof(F34A)=Sof(F35A)=Sof(F36A)=Sof(F37A)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C22(H22)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C21(H21A,H21B), C31(H31A,H31B), C32(H32A,H32B)
6.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C24(H24), C34(H34)
;
_atom_sites_solution_hydrogens   geom
_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
Yb1 Yb 0.47292(2) 0.40246(2) 0.24513(2) 0.02580(6) Uani 1 1 d . . . . .
F11 F 0.4271(3) 0.0011(2) 0.42919(16) 0.0515(6) Uani 1 1 d . . . . .
F12 F 0.2875(3) 0.0521(3) 0.34289(15) 0.0573(7) Uani 1 1 d . . . . .
F13 F 0.2901(3) 0.1446(3) 0.53214(15) 0.0565(7) Uani 1 1 d . . . . .
F14 F 0.1718(3) 0.0075(3) 0.47819(19) 0.0627(8) Uani 1 1 d . . . . .
F15 F 0.0329(3) 0.2213(4) 0.5121(3) 0.0902(12) Uani 1 1 d . . . . .
F16 F 0.1744(3) 0.3378(3) 0.45596(19) 0.0588(7) Uani 1 1 d . . . . .
F17 F 0.0693(4) 0.2118(3) 0.3914(2) 0.0823(11) Uani 1 1 d . . . . .
F18 F 0.8164(2) 0.4095(3) 0.44026(15) 0.0470(6) Uani 1 1 d . . . . .
F19 F 0.6568(2) 0.4645(2) 0.52205(13) 0.0445(5) Uani 1 1 d . . . . .
F20 F 0.7288(3) 0.2674(2) 0.51209(14) 0.0469(6) Uani 1 1 d . . . . .
F21 F 0.6587(3) -0.0112(2) 0.2281(2) 0.0705(10) Uani 1 1 d . . . . .
F22 F 0.8314(4) 0.0080(3) 0.14909(16) 0.0715(10) Uani 1 1 d . . . . .
F23 F 0.7870(4) 0.0916(3) 0.33919(17) 0.0722(9) Uani 1 1 d . . . . .
F24 F 0.9484(3) 0.1399(3) 0.2598(2) 0.0765(11) Uani 1 1 d . . . . .
F25 F 0.8422(3) -0.1642(3) 0.3005(2) 0.0666(8) Uani 1 1 d . . . . .
F26 F 1.0102(4) -0.1081(4) 0.2343(2) 0.0880(13) Uani 1 1 d . . . . .
F27 F 0.9934(4) -0.0676(3) 0.3524(2) 0.0803(10) Uani 1 1 d . . . . .
F28 F 0.7002(3) 0.4814(3) -0.01624(15) 0.0607(7) Uani 1 1 d . . . . .
F29 F 0.8667(4) 0.3487(3) -0.00176(19) 0.0780(10) Uani 1 1 d . . . . .
F30 F 0.8631(3) 0.5345(3) 0.04793(18) 0.0646(8) Uani 1 1 d . . . . .
F38 F -0.0209(3) 0.6172(3) 0.2083(2) 0.0759(10) Uani 1 1 d . . . . .
F39 F -0.0852(3) 0.4344(3) 0.2458(3) 0.0856(12) Uani 1 1 d . . . . .
F40 F 0.0028(3) 0.5573(3) 0.32204(19) 0.0677(9) Uani 1 1 d . . . . .
F31A F 0.2691(8) 0.2215(7) 0.0184(4) 0.0485(14) Uani 0.508(5) 1 d D U P A 1
F32A F 0.1126(6) 0.1437(6) 0.0931(4) 0.0545(12) Uani 0.508(5) 1 d D U P A 1
F33A F 0.2360(9) 0.0251(6) 0.1738(3) 0.0689(14) Uani 0.508(5) 1 d D U P A 1
F34A F 0.4280(8) 0.0469(7) 0.1182(4) 0.0649(13) Uani 0.508(5) 1 d D U P A 1
F35A F 0.3939(9) -0.1496(7) 0.0663(4) 0.0667(15) Uani 0.508(5) 1 d D U P A 1
F36A F 0.1834(8) -0.1111(6) 0.0976(4) 0.0793(15) Uani 0.508(5) 1 d D U P A 1
F37A F 0.2608(9) -0.0360(7) -0.0065(4) 0.0694(15) Uani 0.508(5) 1 d D U P A 1
F31B F 0.3240(8) 0.2126(9) 0.0194(4) 0.0526(15) Uani 0.492(5) 1 d D U P A 2
F32B F 0.1206(7) 0.1818(7) 0.0621(4) 0.0578(14) Uani 0.492(5) 1 d D U P A 2
F33B F 0.3276(8) 0.0329(5) 0.1799(3) 0.0581(13) Uani 0.492(5) 1 d D U P A 2
F34B F 0.4539(7) 0.0796(7) 0.0846(4) 0.0605(12) Uani 0.492(5) 1 d D U P A 2
F35B F 0.3305(11) -0.1693(7) 0.0743(5) 0.0788(17) Uani 0.492(5) 1 d D U P A 2
F36B F 0.1517(9) -0.0714(8) 0.0430(5) 0.0872(16) Uani 0.492(5) 1 d D U P A 2
F37B F 0.3307(10) -0.0323(7) -0.0151(4) 0.0700(15) Uani 0.492(5) 1 d D U P A 2
O1 O 0.3692(3) 0.2839(2) 0.32954(15) 0.0342(5) Uani 1 1 d . . . . .
O2 O 0.6227(3) 0.2430(2) 0.24053(15) 0.0369(6) Uani 1 1 d . . . . .
O3 O 0.3789(3) 0.3164(3) 0.15077(15) 0.0366(6) Uani 1 1 d . . . . .
N1 N 0.5779(3) 0.4426(3) 0.36111(18) 0.0310(6) Uani 1 1 d . . . . .
N2 N 0.6293(3) 0.4613(3) 0.14511(17) 0.0308(6) Uani 1 1 d . . . . .
N3 N 0.2553(3) 0.5099(3) 0.24462(17) 0.0301(6) Uani 1 1 d . . . . .
N4 N 0.4983(3) 0.6377(3) 0.25509(17) 0.0294(6) Uani 1 1 d . . . . .
C11 C 0.5418(4) 0.6684(3) 0.3316(2) 0.0329(7) Uani 1 1 d . . . . .
H11A H 0.463013 0.676684 0.367651 0.039 Uiso 1 1 calc R U . . .
H11B H 0.583377 0.752103 0.329357 0.039 Uiso 1 1 calc R U . . .
C12 C 0.6399(4) 0.5671(4) 0.3607(2) 0.0345(8) Uani 1 1 d . . . . .
H12A H 0.722403 0.562767 0.327405 0.041 Uiso 1 1 calc R U . . .
H12B H 0.663090 0.588710 0.412606 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5986(3) 0.3549(3) 0.4129(2) 0.0305(7) Uani 1 1 d . . . . .
C14 C 0.5286(4) 0.2408(3) 0.4216(2) 0.0316(7) Uani 1 1 d . . . . .
H14 H 0.559062 0.177946 0.456817 0.038 Uiso 1 1 calc R U . . .
C15 C 0.4197(4) 0.2165(3) 0.3821(2) 0.0321(7) Uani 1 1 d . . . . .
C16 C 0.3439(4) 0.0971(4) 0.4036(2) 0.0387(8) Uani 1 1 d . . . . .
C17 C 0.2330(4) 0.1179(4) 0.4672(2) 0.0429(9) Uani 1 1 d . . . . .
C18 C 0.1252(4) 0.2240(5) 0.4564(3) 0.0505(11) Uani 1 1 d . . . . .
C19 C 0.7020(4) 0.3733(4) 0.4714(2) 0.0352(8) Uani 1 1 d . . . . .
C21 C 0.5984(4) 0.6769(3) 0.1953(2) 0.0380(8) Uani 1 1 d . . . . .
H21A H 0.688025 0.668443 0.215616 0.046 Uiso 1 1 calc R U . . .
H21B H 0.579604 0.768217 0.182098 0.046 Uiso 1 1 calc R U . . .
C22 C 0.5974(4) 0.5964(4) 0.1246(2) 0.0401(9) Uani 1 1 d . . . . .
H22 H 0.555230 0.625132 0.076929 0.048 Uiso 1 1 calc R U . . .
C23 C 0.7172(4) 0.3881(4) 0.1066(2) 0.0340(8) Uani 1 1 d . . . . .
C24 C 0.7562(4) 0.2595(4) 0.1270(2) 0.0372(8) Uani 1 1 d . . . . .
H24 H 0.819475 0.213227 0.094219 0.045 Uiso 1 1 calc R U . . .
C25 C 0.7085(4) 0.1995(3) 0.1901(2) 0.0329(7) Uani 1 1 d . . . . .
C26 C 0.7622(4) 0.0623(4) 0.2085(3) 0.0417(9) Uani 1 1 d . . . . .
C27 C 0.8533(4) 0.0576(4) 0.2754(3) 0.0420(9) Uani 1 1 d . . . . .
C28 C 0.9264(5) -0.0739(5) 0.2903(3) 0.0493(10) Uani 1 1 d . . . . .
C29 C 0.7889(5) 0.4374(4) 0.0339(3) 0.0467(10) Uani 1 1 d . . . . .
C31 C 0.3680(4) 0.7071(3) 0.2436(2) 0.0357(8) Uani 1 1 d . . . . .
H31A H 0.356442 0.717436 0.188527 0.043 Uiso 1 1 calc R U . . .
H31B H 0.367614 0.793816 0.265954 0.043 Uiso 1 1 calc R U . . .
C32 C 0.2528(4) 0.6373(4) 0.2793(2) 0.0363(8) Uani 1 1 d . . . . .
H32A H 0.261290 0.628951 0.334752 0.044 Uiso 1 1 calc R U . . .
H32B H 0.167785 0.685649 0.270311 0.044 Uiso 1 1 calc R U . . .
C33 C 0.1482(4) 0.4564(4) 0.2265(2) 0.0356(8) Uani 1 1 d . . . . .
C34 C 0.1466(4) 0.3438(4) 0.1813(2) 0.0391(8) Uani 1 1 d . . . . .
H34 H 0.064397 0.305575 0.176444 0.047 Uiso 1 1 calc R U . . .
C35 C 0.2583(4) 0.2887(4) 0.1446(2) 0.0358(8) Uani 1 1 d . . . . .
C36 C 0.2428(5) 0.1824(4) 0.0871(2) 0.0470(7) Uani 1 1 d D U . . .
C37 C 0.3116(6) 0.0551(5) 0.1067(3) 0.0560(7) Uani 1 1 d D U . . .
C38 C 0.2828(6) -0.0594(5) 0.0585(3) 0.0672(8) Uani 1 1 d D U . . .
C39 C 0.0112(4) 0.5162(5) 0.2511(3) 0.0540(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.189(2) . ?
Yb1 O2 2.181(3) . ?
Yb1 O3 2.187(3) . ?
Yb1 N1 2.409(3) . ?
Yb1 N2 2.400(3) . ?
Yb1 N3 2.407(3) . ?
Yb1 N4 2.492(3) . ?
Yb1 C15 3.131(4) . ?
Yb1 C22 3.182(4) . ?
Yb1 C25 3.204(4) . ?
Yb1 C35 3.166(4) . ?
F11 C16 1.361(5) . ?
F12 C16 1.342(5) . ?
F13 C17 1.350(5) . ?
F14 C17 1.346(5) . ?
F15 C18 1.316(6) . ?
F16 C18 1.313(5) . ?
F17 C18 1.318(6) . ?
F18 C19 1.324(5) . ?
F19 C19 1.353(5) . ?
F20 C19 1.337(4) . ?
F21 C26 1.358(5) . ?
F22 C26 1.338(5) . ?
F23 C27 1.317(5) . ?
F24 C27 1.341(5) . ?
F25 C28 1.309(6) . ?
F26 C28 1.302(6) . ?
F27 C28 1.323(6) . ?
F28 C29 1.352(6) . ?
F29 C29 1.319(5) . ?
F30 C29 1.328(6) . ?
F38 C39 1.328(6) . ?
F39 C39 1.339(5) . ?
F40 C39 1.323(6) . ?
F31A C36 1.294(8) . ?
F32A C36 1.395(8) . ?
F33A C37 1.415(8) . ?
F34A C37 1.202(8) . ?
F35A C38 1.433(9) . ?
F36A C38 1.323(9) . ?
F37A C38 1.202(8) . ?
F31B C36 1.453(8) . ?
F32B C36 1.333(8) . ?
F33B C37 1.328(7) . ?
F34B C37 1.502(9) . ?
F35B C38 1.253(9) . ?
F36B C38 1.379(10) . ?
F37B C38 1.393(9) . ?
O1 C15 1.272(4) . ?
O2 C25 1.273(5) . ?
O3 C35 1.279(5) . ?
N1 C12 1.475(5) . ?
N1 C13 1.305(5) . ?
N2 C22 1.476(5) . ?
N2 C23 1.301(5) . ?
N3 C32 1.467(5) . ?
N3 C33 1.302(5) . ?
N4 C11 1.487(5) . ?
N4 C21 1.490(5) . ?
N4 C31 1.487(5) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.513(5) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.422(5) . ?
C13 C19 1.530(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.372(5) . ?
C15 C16 1.534(5) . ?
C16 C17 1.547(6) . ?
C17 C18 1.525(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.512(6) . ?
C22 H22 1.0000 . ?
C23 C24 1.426(5) . ?
C23 C29 1.537(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.353(6) . ?
C25 C26 1.540(5) . ?
C26 C27 1.536(6) . ?
C27 C28 1.548(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.512(6) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.427(5) . ?
C33 C39 1.525(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.367(6) . ?
C35 C36 1.531(5) . ?
C36 C37 1.510(6) . ?
C37 C38 1.523(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Yb1 N1 76.02(10) . . ?
O1 Yb1 N2 159.75(10) . . ?
O1 Yb1 N3 81.08(10) . . ?
O1 Yb1 N4 125.56(10) . . ?
O1 Yb1 C15 18.79(9) . . ?
O1 Yb1 C22 173.88(10) . . ?
O1 Yb1 C25 99.13(10) . . ?
O1 Yb1 C35 79.64(10) . . ?
O2 Yb1 O1 84.45(10) . . ?
O2 Yb1 O3 88.86(10) . . ?
O2 Yb1 N1 81.08(10) . . ?
O2 Yb1 N2 75.93(10) . . ?
O2 Yb1 N3 157.89(11) . . ?
O2 Yb1 N4 130.27(10) . . ?
O2 Yb1 C15 70.47(10) . . ?
O2 Yb1 C22 101.67(10) . . ?
O2 Yb1 C25 16.47(10) . . ?
O2 Yb1 C35 99.71(10) . . ?
O3 Yb1 O1 92.75(10) . . ?
O3 Yb1 N1 165.53(10) . . ?
O3 Yb1 N2 82.04(10) . . ?
O3 Yb1 N3 75.30(10) . . ?
O3 Yb1 N4 122.87(10) . . ?
O3 Yb1 C15 104.47(10) . . ?
O3 Yb1 C22 87.20(11) . . ?
O3 Yb1 C25 80.80(10) . . ?
O3 Yb1 C35 17.99(10) . . ?
N1 Yb1 N4 71.55(10) . . ?
N1 Yb1 C15 62.39(10) . . ?
N1 Yb1 C22 104.94(11) . . ?
N1 Yb1 C25 91.85(10) . . ?
N1 Yb1 C35 155.47(10) . . ?
N2 Yb1 N1 105.32(10) . . ?
N2 Yb1 N3 116.00(10) . . ?
N2 Yb1 N4 72.59(10) . . ?
N2 Yb1 C15 145.53(10) . . ?
N2 Yb1 C22 26.17(10) . . ?
N2 Yb1 C25 60.78(10) . . ?
N2 Yb1 C35 98.57(10) . . ?
N3 Yb1 N1 111.20(10) . . ?
N3 Yb1 N4 71.82(10) . . ?
N3 Yb1 C15 98.27(10) . . ?
N3 Yb1 C22 93.00(11) . . ?
N3 Yb1 C25 156.07(10) . . ?
N3 Yb1 C35 61.32(10) . . ?
N4 Yb1 C15 125.30(10) . . ?
N4 Yb1 C22 50.26(10) . . ?
N4 Yb1 C25 124.03(10) . . ?
N4 Yb1 C35 122.11(10) . . ?
C15 Yb1 C22 165.48(11) . . ?
C15 Yb1 C25 86.48(10) . . ?
C15 Yb1 C35 94.52(10) . . ?
C22 Yb1 C25 86.90(10) . . ?
C35 Yb1 C22 98.93(11) . . ?
C35 Yb1 C25 95.02(10) . . ?
C15 O1 Yb1 127.5(2) . . ?
C25 O2 Yb1 134.5(2) . . ?
C35 O3 Yb1 130.1(2) . . ?
C12 N1 Yb1 112.9(2) . . ?
C13 N1 Yb1 123.3(2) . . ?
C13 N1 C12 122.8(3) . . ?
C22 N2 Yb1 108.0(2) . . ?
C23 N2 Yb1 128.6(2) . . ?
C23 N2 C22 122.8(3) . . ?
C32 N3 Yb1 111.6(2) . . ?
C33 N3 Yb1 124.8(2) . . ?
C33 N3 C32 122.9(3) . . ?
C11 N4 Yb1 109.8(2) . . ?
C11 N4 C21 110.2(3) . . ?
C11 N4 C31 109.1(3) . . ?
C21 N4 Yb1 108.9(2) . . ?
C31 N4 Yb1 109.1(2) . . ?
C31 N4 C21 109.7(3) . . ?
N4 C11 H11A 109.1 . . ?
N4 C11 H11B 109.1 . . ?
N4 C11 C12 112.4(3) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
N1 C12 C11 108.3(3) . . ?
N1 C12 H12A 110.0 . . ?
N1 C12 H12B 110.0 . . ?
C11 C12 H12A 110.0 . . ?
C11 C12 H12B 110.0 . . ?
H12A C12 H12B 108.4 . . ?
N1 C13 C14 124.9(3) . . ?
N1 C13 C19 119.8(3) . . ?
C14 C13 C19 115.3(3) . . ?
C13 C14 H14 118.2 . . ?
C15 C14 C13 123.7(3) . . ?
C15 C14 H14 118.2 . . ?
O1 C15 Yb1 33.66(16) . . ?
O1 C15 C14 127.7(3) . . ?
O1 C15 C16 114.0(3) . . ?
C14 C15 Yb1 98.0(2) . . ?
C14 C15 C16 118.3(3) . . ?
C16 C15 Yb1 140.9(2) . . ?
F11 C16 C15 111.2(3) . . ?
F11 C16 C17 105.3(3) . . ?
F12 C16 F11 107.2(3) . . ?
F12 C16 C15 110.5(3) . . ?
F12 C16 C17 107.4(3) . . ?
C15 C16 C17 114.9(3) . . ?
F13 C17 C16 108.5(3) . . ?
F13 C17 C18 106.5(4) . . ?
F14 C17 F13 107.5(3) . . ?
F14 C17 C16 108.6(4) . . ?
F14 C17 C18 107.3(3) . . ?
C18 C17 C16 118.1(3) . . ?
F15 C18 F17 108.9(4) . . ?
F15 C18 C17 110.3(4) . . ?
F16 C18 F15 107.9(4) . . ?
F16 C18 F17 107.0(4) . . ?
F16 C18 C17 111.3(4) . . ?
F17 C18 C17 111.3(4) . . ?
F18 C19 F19 107.3(3) . . ?
F18 C19 F20 107.2(3) . . ?
F18 C19 C13 112.8(3) . . ?
F19 C19 C13 110.3(3) . . ?
F20 C19 F19 105.9(3) . . ?
F20 C19 C13 113.0(3) . . ?
N4 C21 H21A 109.2 . . ?
N4 C21 H21B 109.2 . . ?
N4 C21 C22 112.0(3) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
Yb1 C22 H22 124.6 . . ?
N2 C22 Yb1 45.84(16) . . ?
N2 C22 C21 108.4(3) . . ?
N2 C22 H22 124.6 . . ?
C21 C22 Yb1 80.6(2) . . ?
C21 C22 H22 124.6 . . ?
N2 C23 C24 124.5(3) . . ?
N2 C23 C29 120.9(3) . . ?
C24 C23 C29 114.5(3) . . ?
C23 C24 H24 118.0 . . ?
C25 C24 C23 123.9(3) . . ?
C25 C24 H24 118.0 . . ?
O2 C25 Yb1 29.05(16) . . ?
O2 C25 C24 128.1(3) . . ?
O2 C25 C26 112.3(3) . . ?
C24 C25 Yb1 100.1(2) . . ?
C24 C25 C26 119.6(4) . . ?
C26 C25 Yb1 139.7(3) . . ?
F21 C26 C25 109.4(3) . . ?
F21 C26 C27 107.1(4) . . ?
F22 C26 F21 108.4(4) . . ?
F22 C26 C25 111.8(4) . . ?
F22 C26 C27 107.4(3) . . ?
C27 C26 C25 112.7(3) . . ?
F23 C27 F24 109.2(4) . . ?
F23 C27 C26 111.2(4) . . ?
F23 C27 C28 106.9(4) . . ?
F24 C27 C26 107.4(3) . . ?
F24 C27 C28 106.1(4) . . ?
C26 C27 C28 115.7(4) . . ?
F25 C28 F27 107.9(4) . . ?
F25 C28 C27 111.2(4) . . ?
F26 C28 F25 108.0(5) . . ?
F26 C28 F27 108.1(4) . . ?
F26 C28 C27 111.9(4) . . ?
F27 C28 C27 109.6(4) . . ?
F28 C29 C23 110.8(4) . . ?
F29 C29 F28 106.5(4) . . ?
F29 C29 F30 107.4(4) . . ?
F29 C29 C23 113.5(4) . . ?
F30 C29 F28 106.6(4) . . ?
F30 C29 C23 111.7(4) . . ?
N4 C31 H31A 109.2 . . ?
N4 C31 H31B 109.2 . . ?
N4 C31 C32 112.2(3) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
N3 C32 C31 107.9(3) . . ?
N3 C32 H32A 110.1 . . ?
N3 C32 H32B 110.1 . . ?
C31 C32 H32A 110.1 . . ?
C31 C32 H32B 110.1 . . ?
H32A C32 H32B 108.4 . . ?
N3 C33 C34 124.8(4) . . ?
N3 C33 C39 120.4(3) . . ?
C34 C33 C39 114.8(3) . . ?
C33 C34 H34 118.6 . . ?
C35 C34 C33 122.9(4) . . ?
C35 C34 H34 118.6 . . ?
O3 C35 Yb1 31.88(17) . . ?
O3 C35 C34 127.9(4) . . ?
O3 C35 C36 113.5(4) . . ?
C34 C35 Yb1 98.4(2) . . ?
C34 C35 C36 118.7(4) . . ?
C36 C35 Yb1 141.2(3) . . ?
F31A C36 F32A 108.9(5) . . ?
F31A C36 C35 111.2(5) . . ?
F31A C36 C37 114.5(5) . . ?
F32A C36 C35 109.5(4) . . ?
F32A C36 C37 97.6(4) . . ?
F31B C36 C35 107.0(5) . . ?
F31B C36 C37 98.7(5) . . ?
F32B C36 F31B 103.3(5) . . ?
F32B C36 C35 113.3(5) . . ?
F32B C36 C37 117.9(5) . . ?
C37 C36 C35 114.2(4) . . ?
F33A C37 C36 99.7(5) . . ?
F33A C37 C38 99.2(5) . . ?
F34A C37 F33A 109.8(6) . . ?
F34A C37 C36 121.0(5) . . ?
F34A C37 C38 107.6(5) . . ?
F33B C37 F34B 97.0(6) . . ?
F33B C37 C36 116.2(4) . . ?
F33B C37 C38 116.9(5) . . ?
F34B C37 C36 101.2(4) . . ?
F34B C37 C38 104.1(5) . . ?
C36 C37 C38 116.7(4) . . ?
F35A C38 C37 105.1(5) . . ?
F36A C38 F35A 104.4(6) . . ?
F36A C38 C37 103.3(5) . . ?
F37A C38 F35A 113.0(7) . . ?
F37A C38 F36A 113.9(7) . . ?
F37A C38 C37 115.8(6) . . ?
F35B C38 F36B 107.1(7) . . ?
F35B C38 F37B 106.4(7) . . ?
F35B C38 C37 120.2(6) . . ?
F36B C38 F37B 97.6(6) . . ?
F36B C38 C37 116.3(6) . . ?
F37B C38 C37 106.3(5) . . ?
F38 C39 F39 106.7(4) . . ?
F38 C39 C33 111.2(4) . . ?
F39 C39 C33 112.5(4) . . ?
F40 C39 F38 106.3(4) . . ?
F40 C39 F39 106.4(4) . . ?
F40 C39 C33 113.4(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Yb1 O1 C15 C14 32.3(6) . . . . ?
Yb1 O1 C15 C16 -149.7(3) . . . . ?
Yb1 O2 C25 C24 17.9(6) . . . . ?
Yb1 O2 C25 C26 -163.6(3) . . . . ?
Yb1 O3 C35 C34 25.9(6) . . . . ?
Yb1 O3 C35 C36 -155.6(3) . . . . ?
Yb1 N1 C12 C11 46.6(3) . . . . ?
Yb1 N1 C13 C14 -21.2(5) . . . . ?
Yb1 N1 C13 C19 160.7(2) . . . . ?
Yb1 N2 C22 C21 55.7(4) . . . . ?
Yb1 N2 C23 C24 -13.3(5) . . . . ?
Yb1 N2 C23 C29 167.2(3) . . . . ?
Yb1 N3 C32 C31 49.6(3) . . . . ?
Yb1 N3 C33 C34 -21.9(6) . . . . ?
Yb1 N3 C33 C39 160.6(3) . . . . ?
Yb1 N4 C11 C12 37.8(3) . . . . ?
Yb1 N4 C21 C22 32.0(4) . . . . ?
Yb1 N4 C31 C32 37.7(4) . . . . ?
Yb1 C15 C16 F11 124.1(3) . . . . ?
Yb1 C15 C16 F12 5.2(6) . . . . ?
Yb1 C15 C16 C17 -116.4(4) . . . . ?
Yb1 C25 C26 F21 35.4(5) . . . . ?
Yb1 C25 C26 F22 155.5(3) . . . . ?
Yb1 C25 C26 C27 -83.5(5) . . . . ?
Yb1 C35 C36 F31A -89.8(6) . . . . ?
Yb1 C35 C36 F32A 149.8(4) . . . . ?
Yb1 C35 C36 F31B -66.5(6) . . . . ?
Yb1 C35 C36 F32B -179.6(5) . . . . ?
Yb1 C35 C36 C37 41.6(6) . . . . ?
F11 C16 C17 F13 56.9(4) . . . . ?
F11 C16 C17 F14 -59.6(4) . . . . ?
F11 C16 C17 C18 178.1(4) . . . . ?
F12 C16 C17 F13 170.9(3) . . . . ?
F12 C16 C17 F14 54.3(4) . . . . ?
F12 C16 C17 C18 -68.0(5) . . . . ?
F13 C17 C18 F15 -63.4(5) . . . . ?
F13 C17 C18 F16 56.2(5) . . . . ?
F13 C17 C18 F17 175.5(4) . . . . ?
F14 C17 C18 F15 51.4(5) . . . . ?
F14 C17 C18 F16 171.1(4) . . . . ?
F14 C17 C18 F17 -69.6(5) . . . . ?
F21 C26 C27 F23 -54.4(4) . . . . ?
F21 C26 C27 F24 -173.9(4) . . . . ?
F21 C26 C27 C28 67.8(5) . . . . ?
F22 C26 C27 F23 -170.6(4) . . . . ?
F22 C26 C27 F24 69.9(4) . . . . ?
F22 C26 C27 C28 -48.4(5) . . . . ?
F23 C27 C28 F25 68.4(5) . . . . ?
F23 C27 C28 F26 -170.8(4) . . . . ?
F23 C27 C28 F27 -50.9(5) . . . . ?
F24 C27 C28 F25 -175.1(4) . . . . ?
F24 C27 C28 F26 -54.3(5) . . . . ?
F24 C27 C28 F27 65.6(5) . . . . ?
F31A C36 C37 F33A -164.7(6) . . . . ?
F31A C36 C37 F34A 75.1(8) . . . . ?
F31A C36 C37 C38 -59.1(7) . . . . ?
F32A C36 C37 F33A -49.9(6) . . . . ?
F32A C36 C37 F34A -170.1(6) . . . . ?
F32A C36 C37 C38 55.7(6) . . . . ?
F33A C37 C38 F35A -96.9(6) . . . . ?
F33A C37 C38 F36A 12.3(7) . . . . ?
F33A C37 C38 F37A 137.6(8) . . . . ?
F34A C37 C38 F35A 17.4(7) . . . . ?
F34A C37 C38 F36A 126.7(7) . . . . ?
F34A C37 C38 F37A -108.1(9) . . . . ?
F31B C36 C37 F33B 139.9(7) . . . . ?
F31B C36 C37 F34B 36.3(5) . . . . ?
F31B C36 C37 C38 -75.9(6) . . . . ?
F32B C36 C37 F33B -110.0(7) . . . . ?
F32B C36 C37 F34B 146.5(6) . . . . ?
F32B C36 C37 C38 34.3(7) . . . . ?
F33B C37 C38 F35B -32.0(11) . . . . ?
F33B C37 C38 F36B 100.0(8) . . . . ?
F33B C37 C38 F37B -152.6(7) . . . . ?
F34B C37 C38 F35B 73.5(9) . . . . ?
F34B C37 C38 F36B -154.5(6) . . . . ?
F34B C37 C38 F37B -47.1(7) . . . . ?
O1 C15 C16 F11 150.4(3) . . . . ?
O1 C15 C16 F12 31.5(5) . . . . ?
O1 C15 C16 C17 -90.1(4) . . . . ?
O2 C25 C26 F21 47.6(5) . . . . ?
O2 C25 C26 F22 167.7(3) . . . . ?
O2 C25 C26 C27 -71.3(5) . . . . ?
O3 C35 C36 F31A -69.5(6) . . . . ?
O3 C35 C36 F32A 170.1(4) . . . . ?
O3 C35 C36 F31B -46.1(5) . . . . ?
O3 C35 C36 F32B -159.3(5) . . . . ?
O3 C35 C36 C37 62.0(5) . . . . ?
N1 C13 C14 C15 -8.1(6) . . . . ?
N1 C13 C19 F18 -47.4(5) . . . . ?
N1 C13 C19 F19 72.6(4) . . . . ?
N1 C13 C19 F20 -169.1(3) . . . . ?
N2 C23 C24 C25 -1.8(6) . . . . ?
N2 C23 C29 F28 -55.1(5) . . . . ?
N2 C23 C29 F29 -174.8(4) . . . . ?
N2 C23 C29 F30 63.6(5) . . . . ?
N3 C33 C34 C35 -8.0(7) . . . . ?
N3 C33 C39 F38 76.8(5) . . . . ?
N3 C33 C39 F39 -163.6(4) . . . . ?
N3 C33 C39 F40 -42.8(6) . . . . ?
N4 C11 C12 N1 -56.9(4) . . . . ?
N4 C21 C22 Yb1 -23.5(3) . . . . ?
N4 C21 C22 N2 -60.4(4) . . . . ?
N4 C31 C32 N3 -59.4(4) . . . . ?
C11 N4 C21 C22 152.6(3) . . . . ?
C11 N4 C31 C32 -82.3(4) . . . . ?
C12 N1 C13 C14 171.5(3) . . . . ?
C12 N1 C13 C19 -6.7(5) . . . . ?
C13 N1 C12 C11 -144.8(3) . . . . ?
C13 C14 C15 Yb1 22.3(4) . . . . ?
C13 C14 C15 O1 4.9(6) . . . . ?
C13 C14 C15 C16 -173.0(4) . . . . ?
C14 C13 C19 F18 134.3(3) . . . . ?
C14 C13 C19 F19 -105.7(4) . . . . ?
C14 C13 C19 F20 12.6(5) . . . . ?
C14 C15 C16 F11 -31.4(5) . . . . ?
C14 C15 C16 F12 -150.3(4) . . . . ?
C14 C15 C16 C17 88.1(4) . . . . ?
C15 C16 C17 F13 -65.8(4) . . . . ?
C15 C16 C17 F14 177.7(3) . . . . ?
C15 C16 C17 C18 55.4(5) . . . . ?
C16 C17 C18 F15 174.4(4) . . . . ?
C16 C17 C18 F16 -65.9(5) . . . . ?
C16 C17 C18 F17 53.4(5) . . . . ?
C19 C13 C14 C15 170.1(3) . . . . ?
C21 N4 C11 C12 -82.2(4) . . . . ?
C21 N4 C31 C32 156.9(3) . . . . ?
C22 N2 C23 C24 176.3(4) . . . . ?
C22 N2 C23 C29 -3.2(6) . . . . ?
C23 N2 C22 Yb1 172.2(4) . . . . ?
C23 N2 C22 C21 -132.1(4) . . . . ?
C23 C24 C25 Yb1 9.8(4) . . . . ?
C23 C24 C25 O2 1.1(7) . . . . ?
C23 C24 C25 C26 -177.3(4) . . . . ?
C24 C23 C29 F28 125.4(4) . . . . ?
C24 C23 C29 F29 5.6(6) . . . . ?
C24 C23 C29 F30 -115.9(4) . . . . ?
C24 C25 C26 F21 -133.8(4) . . . . ?
C24 C25 C26 F22 -13.7(5) . . . . ?
C24 C25 C26 C27 107.3(4) . . . . ?
C25 C26 C27 F23 65.9(5) . . . . ?
C25 C26 C27 F24 -53.6(5) . . . . ?
C25 C26 C27 C28 -171.9(4) . . . . ?
C26 C27 C28 F25 -56.1(6) . . . . ?
C26 C27 C28 F26 64.7(6) . . . . ?
C26 C27 C28 F27 -175.4(4) . . . . ?
C29 C23 C24 C25 177.7(4) . . . . ?
C31 N4 C11 C12 157.3(3) . . . . ?
C31 N4 C21 C22 -87.3(4) . . . . ?
C32 N3 C33 C34 168.7(4) . . . . ?
C32 N3 C33 C39 -8.9(6) . . . . ?
C33 N3 C32 C31 -139.6(4) . . . . ?
C33 C34 C35 Yb1 22.1(4) . . . . ?
C33 C34 C35 O3 8.6(7) . . . . ?
C33 C34 C35 C36 -169.8(4) . . . . ?
C34 C33 C39 F38 -101.0(4) . . . . ?
C34 C33 C39 F39 18.6(6) . . . . ?
C34 C33 C39 F40 139.4(4) . . . . ?
C34 C35 C36 F31A 109.2(6) . . . . ?
C34 C35 C36 F32A -11.2(6) . . . . ?
C34 C35 C36 F31B 132.6(5) . . . . ?
C34 C35 C36 F32B 19.4(6) . . . . ?
C34 C35 C36 C37 -119.3(5) . . . . ?
C35 C36 C37 F33A 65.5(6) . . . . ?
C35 C36 C37 F34A -54.7(7) . . . . ?
C35 C36 C37 F33B 26.8(7) . . . . ?
C35 C36 C37 F34B -76.8(5) . . . . ?
C35 C36 C37 C38 171.0(4) . . . . ?
C36 C37 C38 F35A 157.3(5) . . . . ?
C36 C37 C38 F36A -93.5(6) . . . . ?
C36 C37 C38 F37A 31.7(9) . . . . ?
C36 C37 C38 F35B -175.9(8) . . . . ?
C36 C37 C38 F36B -44.0(8) . . . . ?
C36 C37 C38 F37B 63.4(7) . . . . ?
C39 C33 C34 C35 169.7(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_dal2161
_database_code_depnum_ccdc_archive 'CCDC 2313984'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 F9 N4 O3 Yb, C4 H10 O'
_chemical_formula_sum            'C25 H34 F9 N4 O4 Yb'
_chemical_formula_weight         798.60
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   19.7260(19)
_cell_length_b                   19.9703(19)
_cell_length_c                   15.5564(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6128.2(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9630
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      26.33
_cell_measurement_theta_min      2.424
_shelx_estimated_absorpt_T_max   0.885
_shelx_estimated_absorpt_T_min   0.602
_exptl_absorpt_coefficient_mu    3.144
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8585
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0721 before and 0.0571 after correction.
The Ratio of minimum to maximum transmission is 0.8585.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       lath-like
_exptl_crystal_F_000             3160
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            106067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.411
_diffrn_reflns_theta_min         1.954
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex'
_diffrn_measurement_method       'CCD Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5488
_reflns_number_total             6289
_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       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.434
_refine_diff_density_min         -2.355
_refine_diff_density_rms         0.130
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.186
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.186
_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)+54.2407P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0848
_refine_ls_wR_factor_ref         0.0881
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C31(H31A,H31B), C32(H32A,H32B), C21(H21A,
 H21B), C22(H22A,H22B), C43(H43A,H43B), C42(H42A,H42B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C34(H34), C24(H24)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C37(H37A,H37B,H37C), C27(H27A,H27B,H27C), C41(H41A,H41B,
 H41C), C44(H44A,H44B,H44C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Yb1 Yb 0.27043(2) 0.47043(2) 0.45916(2) 0.02179(7) Uani 1 1 d . . . . .
O1 O 0.33221(19) 0.40120(18) 0.5362(3) 0.0281(8) Uani 1 1 d . . . . .
O2 O 0.3374(2) 0.4458(2) 0.3510(2) 0.0303(9) Uani 1 1 d . . . . .
O3 O 0.2139(2) 0.38107(18) 0.4186(2) 0.0285(9) Uani 1 1 d . . . . .
F13 F 0.3286(2) 0.23990(18) 0.6274(3) 0.0552(12) Uani 1 1 d . . . . .
F33 F 0.2529(2) 0.2667(2) 0.3253(3) 0.0657(13) Uani 1 1 d . . . . .
N1 N 0.2085(2) 0.4617(2) 0.5931(3) 0.0254(10) Uani 1 1 d . . . . .
F32 F 0.1571(3) 0.2579(2) 0.3843(3) 0.0733(15) Uani 1 1 d . . . . .
F21 F 0.4990(2) 0.3790(3) 0.3147(4) 0.0761(16) Uani 1 1 d . . . . .
N4 N 0.2274(2) 0.5791(2) 0.5020(3) 0.0261(10) Uani 1 1 d . . . . .
N3 N 0.1909(2) 0.5146(2) 0.3517(3) 0.0250(10) Uani 1 1 d . . . . .
F11 F 0.4127(2) 0.3045(2) 0.6189(5) 0.098(2) Uani 1 1 d . . . . .
F31 F 0.1644(3) 0.2758(2) 0.2490(3) 0.0682(14) Uani 1 1 d . . . . .
N2 N 0.3629(2) 0.5520(2) 0.4743(3) 0.0279(10) Uani 1 1 d . . . . .
F12 F 0.3652(3) 0.2694(2) 0.5045(4) 0.094(2) Uani 1 1 d . . . . .
C15 C 0.3085(3) 0.3532(3) 0.5827(3) 0.0253(11) Uani 1 1 d . . . . .
C14 C 0.2517(3) 0.3528(3) 0.6325(4) 0.0287(12) Uani 1 1 d . . . . .
H14 H 0.240404 0.312296 0.661179 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1611(3) 0.5691(3) 0.5441(4) 0.0312(12) Uani 1 1 d . . . . .
H11A H 0.128129 0.552190 0.501322 0.037 Uiso 1 1 calc R U . . .
H11B H 0.144296 0.612559 0.565903 0.037 Uiso 1 1 calc R U . . .
F23 F 0.4194(4) 0.3855(4) 0.2239(3) 0.137(3) Uani 1 1 d . . . . .
C12 C 0.1660(3) 0.5192(3) 0.6189(4) 0.0318(13) Uani 1 1 d . . . . .
H12A H 0.186279 0.541505 0.669623 0.038 Uiso 1 1 calc R U . . .
H12B H 0.120140 0.503441 0.634799 0.038 Uiso 1 1 calc R U . . .
C34 C 0.1664(3) 0.4093(3) 0.2827(4) 0.0303(12) Uani 1 1 d . . . . .
H34 H 0.152076 0.390182 0.229889 0.036 Uiso 1 1 calc R U . . .
C31 C 0.2198(3) 0.6201(3) 0.4238(4) 0.0298(12) Uani 1 1 d . . . . .
H31A H 0.265056 0.628225 0.398376 0.036 Uiso 1 1 calc R U . . .
H31B H 0.200106 0.664026 0.439529 0.036 Uiso 1 1 calc R U . . .
C33 C 0.1607(3) 0.4807(3) 0.2917(4) 0.0285(12) Uani 1 1 d . . . . .
F22 F 0.4089(3) 0.3283(3) 0.3338(5) 0.099(2) Uani 1 1 d . . . . .
C17 C 0.1606(3) 0.4066(3) 0.7205(4) 0.0373(14) Uani 1 1 d . . . . .
H17A H 0.170613 0.443699 0.759717 0.056 Uiso 1 1 calc R U . . .
H17B H 0.166930 0.363964 0.750562 0.056 Uiso 1 1 calc R U . . .
H17C H 0.113513 0.410114 0.700712 0.056 Uiso 1 1 calc R U . . .
C32 C 0.1747(3) 0.5866(3) 0.3575(4) 0.0291(12) Uani 1 1 d . . . . .
H32A H 0.126577 0.592346 0.373831 0.035 Uiso 1 1 calc R U . . .
H32B H 0.181635 0.607966 0.300705 0.035 Uiso 1 1 calc R U . . .
C16 C 0.3534(3) 0.2920(3) 0.5831(5) 0.0412(16) Uani 1 1 d . . . . .
C21 C 0.2772(3) 0.6084(3) 0.5623(4) 0.0316(13) Uani 1 1 d . . . . .
H21A H 0.280156 0.580050 0.614376 0.038 Uiso 1 1 calc R U . . .
H21B H 0.261660 0.653448 0.580097 0.038 Uiso 1 1 calc R U . . .
C37 C 0.1150(3) 0.5144(3) 0.2263(4) 0.0419(16) Uani 1 1 d . . . . .
H37A H 0.076745 0.535511 0.255887 0.063 Uiso 1 1 calc R U . . .
H37B H 0.098043 0.480914 0.185594 0.063 Uiso 1 1 calc R U . . .
H37C H 0.140833 0.548594 0.195087 0.063 Uiso 1 1 calc R U . . .
C13 C 0.2074(3) 0.4098(3) 0.6446(4) 0.0274(12) Uani 1 1 d . . . . .
C35 C 0.1906(3) 0.3672(3) 0.3435(4) 0.0272(12) Uani 1 1 d . . . . .
C22 C 0.3470(3) 0.6139(3) 0.5212(4) 0.0309(13) Uani 1 1 d . . . . .
H22A H 0.347865 0.652403 0.481117 0.037 Uiso 1 1 calc R U . . .
H22B H 0.381538 0.621689 0.566253 0.037 Uiso 1 1 calc R U . . .
C24 C 0.4448(3) 0.4904(3) 0.3902(4) 0.0387(15) Uani 1 1 d . . . . .
H24 H 0.492199 0.483543 0.383388 0.046 Uiso 1 1 calc R U . . .
C25 C 0.4025(3) 0.4454(3) 0.3525(4) 0.0334(13) Uani 1 1 d . . . . .
C36 C 0.1905(4) 0.2919(3) 0.3252(4) 0.0397(15) Uani 1 1 d . . . . .
O4 O 0.5124(4) 0.3642(5) 0.9137(5) 0.107(3) Uani 1 1 d . . . . .
C23 C 0.4234(3) 0.5481(3) 0.4399(4) 0.0336(14) Uani 1 1 d . . . . .
C27 C 0.4749(3) 0.6032(4) 0.4468(5) 0.0462(17) Uani 1 1 d . . . . .
H27A H 0.461018 0.640985 0.410671 0.069 Uiso 1 1 calc R U . . .
H27B H 0.519168 0.586680 0.427578 0.069 Uiso 1 1 calc R U . . .
H27C H 0.478207 0.617973 0.506770 0.069 Uiso 1 1 calc R U . . .
C26 C 0.4329(4) 0.3861(4) 0.3033(5) 0.0460(17) Uani 1 1 d . . . . .
C43 C 0.5381(7) 0.3474(8) 1.0034(10) 0.134(6) Uani 1 1 d . . . . .
H43A H 0.507371 0.317289 1.035599 0.161 Uiso 1 1 calc R U . . .
H43B H 0.584923 0.329532 1.003582 0.161 Uiso 1 1 calc R U . . .
C41 C 0.4933(7) 0.3032(7) 0.7855(9) 0.124(5) Uani 1 1 d . . . . .
H41A H 0.443684 0.304088 0.788367 0.186 Uiso 1 1 calc R U . . .
H41B H 0.508029 0.263731 0.753129 0.186 Uiso 1 1 calc R U . . .
H41C H 0.509550 0.343806 0.756626 0.186 Uiso 1 1 calc R U . . .
C42 C 0.5219(7) 0.3003(7) 0.8748(8) 0.115(5) Uani 1 1 d . . . . .
H42A H 0.498329 0.265395 0.908669 0.138 Uiso 1 1 calc R U . . .
H42B H 0.570747 0.289208 0.872709 0.138 Uiso 1 1 calc R U . . .
C44 C 0.5341(6) 0.4155(8) 1.0307(12) 0.140(6) Uani 1 1 d . . . . .
H44A H 0.495824 0.437411 1.002127 0.210 Uiso 1 1 calc R U . . .
H44B H 0.576232 0.438704 1.015698 0.210 Uiso 1 1 calc R U . . .
H44C H 0.527534 0.417040 1.093133 0.210 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Yb1 O1 2.199(4) . ?
Yb1 O2 2.195(4) . ?
Yb1 O3 2.197(4) . ?
Yb1 N1 2.422(4) . ?
Yb1 N4 2.423(4) . ?
Yb1 N3 2.456(5) . ?
Yb1 N2 2.457(5) . ?
Yb1 C15 3.120(5) . ?
Yb1 C31 3.199(5) . ?
Yb1 C21 3.191(6) . ?
Yb1 C35 3.156(6) . ?
Yb1 C25 3.129(6) . ?
O1 C15 1.289(6) . ?
O2 C25 1.286(7) . ?
O3 C35 1.286(7) . ?
F13 C16 1.340(7) . ?
F33 C36 1.329(8) . ?
N1 C12 1.477(7) . ?
N1 C13 1.310(7) . ?
F32 C36 1.319(8) . ?
F21 C26 1.323(8) . ?
N4 C11 1.476(7) . ?
N4 C31 1.474(7) . ?
N4 C21 1.479(7) . ?
N3 C33 1.299(7) . ?
N3 C32 1.475(7) . ?
F11 C16 1.318(8) . ?
F31 C36 1.332(8) . ?
N2 C22 1.469(7) . ?
N2 C23 1.310(8) . ?
F12 C16 1.325(9) . ?
C15 C14 1.361(8) . ?
C15 C16 1.510(8) . ?
C14 H14 0.9500 . ?
C14 C13 1.448(8) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.534(8) . ?
F23 C26 1.263(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C34 H34 0.9500 . ?
C34 C33 1.436(8) . ?
C34 C35 1.352(8) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.517(8) . ?
C33 C37 1.518(8) . ?
F22 C26 1.336(9) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 C13 1.501(8) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.522(8) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C35 C36 1.532(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C24 H24 0.9500 . ?
C24 C25 1.359(9) . ?
C24 C23 1.450(9) . ?
C25 C26 1.532(9) . ?
O4 C43 1.521(16) . ?
O4 C42 1.424(15) . ?
C23 C27 1.502(8) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 C44 1.427(18) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C41 C42 1.501(17) . ?
C42 H42A 0.9900 . ?
C42 H42B 0.9900 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Yb1 N1 76.43(15) . . ?
O1 Yb1 N4 127.39(15) . . ?
O1 Yb1 N3 161.99(14) . . ?
O1 Yb1 N2 87.32(15) . . ?
O1 Yb1 C15 19.79(14) . . ?
O1 Yb1 C31 148.69(15) . . ?
O1 Yb1 C21 104.22(15) . . ?
O1 Yb1 C35 100.18(15) . . ?
O1 Yb1 C25 74.17(15) . . ?
O2 Yb1 O1 86.77(15) . . ?
O2 Yb1 O3 84.45(15) . . ?
O2 Yb1 N1 161.26(15) . . ?
O2 Yb1 N4 128.48(15) . . ?
O2 Yb1 N3 86.73(15) . . ?
O2 Yb1 N2 77.02(16) . . ?
O2 Yb1 C15 99.18(15) . . ?
O2 Yb1 C31 105.39(15) . . ?
O2 Yb1 C21 123.64(15) . . ?
O2 Yb1 C35 73.52(15) . . ?
O2 Yb1 C25 19.40(16) . . ?
O3 Yb1 O1 85.81(14) . . ?
O3 Yb1 N1 86.08(15) . . ?
O3 Yb1 N4 128.94(15) . . ?
O3 Yb1 N3 76.85(14) . . ?
O3 Yb1 N2 160.56(15) . . ?
O3 Yb1 C15 71.91(14) . . ?
O3 Yb1 C31 123.45(15) . . ?
O3 Yb1 C21 150.10(15) . . ?
O3 Yb1 C35 18.72(14) . . ?
O3 Yb1 C25 98.10(16) . . ?
N1 Yb1 N4 69.60(15) . . ?
N1 Yb1 N3 106.79(15) . . ?
N1 Yb1 N2 109.91(16) . . ?
N1 Yb1 C15 62.44(15) . . ?
N1 Yb1 C31 93.32(15) . . ?
N1 Yb1 C21 69.58(15) . . ?
N1 Yb1 C35 101.04(15) . . ?
N1 Yb1 C25 149.87(15) . . ?
N4 Yb1 N3 69.01(15) . . ?
N4 Yb1 N2 68.90(16) . . ?
N4 Yb1 C15 125.91(15) . . ?
N4 Yb1 C31 26.02(15) . . ?
N4 Yb1 C21 26.27(15) . . ?
N4 Yb1 C35 124.53(15) . . ?
N4 Yb1 C25 125.48(16) . . ?
N3 Yb1 N2 107.51(15) . . ?
N3 Yb1 C15 147.40(14) . . ?
N3 Yb1 C31 49.29(15) . . ?
N3 Yb1 C21 93.36(15) . . ?
N3 Yb1 C35 61.85(15) . . ?
N3 Yb1 C25 103.20(15) . . ?
N2 Yb1 C15 105.06(15) . . ?
N2 Yb1 C31 68.21(15) . . ?
N2 Yb1 C21 49.34(15) . . ?
N2 Yb1 C35 149.05(15) . . ?
N2 Yb1 C25 62.51(17) . . ?
C15 Yb1 C31 151.87(14) . . ?
C15 Yb1 C21 109.14(15) . . ?
C15 Yb1 C35 88.94(14) . . ?
C15 Yb1 C25 90.37(15) . . ?
C21 Yb1 C31 44.99(15) . . ?
C35 Yb1 C31 110.87(15) . . ?
C35 Yb1 C21 150.60(15) . . ?
C25 Yb1 C31 108.54(16) . . ?
C25 Yb1 C21 111.69(16) . . ?
C25 Yb1 C35 90.50(16) . . ?
C15 O1 Yb1 124.9(3) . . ?
C25 O2 Yb1 126.0(4) . . ?
C35 O3 Yb1 128.0(3) . . ?
C12 N1 Yb1 117.6(3) . . ?
C13 N1 Yb1 126.3(4) . . ?
C13 N1 C12 116.1(5) . . ?
C11 N4 Yb1 108.1(3) . . ?
C11 N4 C21 111.1(5) . . ?
C31 N4 Yb1 107.8(3) . . ?
C31 N4 C11 110.5(5) . . ?
C31 N4 C21 111.8(4) . . ?
C21 N4 Yb1 107.3(3) . . ?
C33 N3 Yb1 126.5(4) . . ?
C33 N3 C32 116.9(5) . . ?
C32 N3 Yb1 116.6(3) . . ?
C22 N2 Yb1 116.5(3) . . ?
C23 N2 Yb1 126.7(4) . . ?
C23 N2 C22 116.6(5) . . ?
O1 C15 Yb1 35.3(2) . . ?
O1 C15 C14 128.5(5) . . ?
O1 C15 C16 113.0(5) . . ?
C14 C15 Yb1 99.0(4) . . ?
C14 C15 C16 118.3(5) . . ?
C16 C15 Yb1 138.7(4) . . ?
C15 C14 H14 117.8 . . ?
C15 C14 C13 124.4(5) . . ?
C13 C14 H14 117.8 . . ?
Yb1 C11 H11A 87.5 . . ?
Yb1 C11 H11B 155.0 . . ?
N4 C11 Yb1 45.9(2) . . ?
N4 C11 H11A 109.3 . . ?
N4 C11 H11B 109.3 . . ?
N4 C11 C12 111.6(5) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 Yb1 82.6(3) . . ?
C12 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N1 C12 C11 109.5(5) . . ?
N1 C12 H12A 109.8 . . ?
N1 C12 H12B 109.8 . . ?
C11 C12 H12A 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
C33 C34 H34 117.4 . . ?
C35 C34 H34 117.4 . . ?
C35 C34 C33 125.2(5) . . ?
Yb1 C31 H31A 86.6 . . ?
Yb1 C31 H31B 155.2 . . ?
N4 C31 Yb1 46.1(2) . . ?
N4 C31 H31A 109.2 . . ?
N4 C31 H31B 109.2 . . ?
N4 C31 C32 112.1(4) . . ?
H31A C31 H31B 107.9 . . ?
C32 C31 Yb1 83.6(3) . . ?
C32 C31 H31A 109.2 . . ?
C32 C31 H31B 109.2 . . ?
N3 C33 C34 123.5(5) . . ?
N3 C33 C37 121.5(5) . . ?
C34 C33 C37 114.9(5) . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
N3 C32 C31 110.1(4) . . ?
N3 C32 H32A 109.6 . . ?
N3 C32 H32B 109.6 . . ?
C31 C32 H32A 109.6 . . ?
C31 C32 H32B 109.6 . . ?
H32A C32 H32B 108.2 . . ?
F13 C16 C15 114.6(5) . . ?
F11 C16 F13 104.7(6) . . ?
F11 C16 F12 107.4(7) . . ?
F11 C16 C15 111.6(5) . . ?
F12 C16 F13 105.9(6) . . ?
F12 C16 C15 112.1(6) . . ?
Yb1 C21 H21A 85.4 . . ?
Yb1 C21 H21B 155.8 . . ?
N4 C21 Yb1 46.5(2) . . ?
N4 C21 H21A 109.4 . . ?
N4 C21 H21B 109.4 . . ?
N4 C21 C22 111.3(5) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 Yb1 83.6(3) . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C33 C37 H37A 109.5 . . ?
C33 C37 H37B 109.5 . . ?
C33 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N1 C13 C14 122.2(5) . . ?
N1 C13 C17 121.6(5) . . ?
C14 C13 C17 116.2(5) . . ?
O3 C35 Yb1 33.2(2) . . ?
O3 C35 C34 128.9(5) . . ?
O3 C35 C36 112.4(5) . . ?
C34 C35 Yb1 99.7(4) . . ?
C34 C35 C36 118.7(5) . . ?
C36 C35 Yb1 138.4(4) . . ?
N2 C22 C21 110.0(5) . . ?
N2 C22 H22A 109.7 . . ?
N2 C22 H22B 109.7 . . ?
C21 C22 H22A 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
C25 C24 H24 117.4 . . ?
C25 C24 C23 125.2(6) . . ?
C23 C24 H24 117.4 . . ?
O2 C25 Yb1 34.6(3) . . ?
O2 C25 C24 128.2(6) . . ?
O2 C25 C26 112.7(6) . . ?
C24 C25 Yb1 100.2(4) . . ?
C24 C25 C26 119.1(6) . . ?
C26 C25 Yb1 135.6(5) . . ?
F33 C36 F31 105.6(6) . . ?
F33 C36 C35 111.7(5) . . ?
F32 C36 F33 105.5(6) . . ?
F32 C36 F31 107.6(6) . . ?
F32 C36 C35 112.1(5) . . ?
F31 C36 C35 113.8(5) . . ?
C42 O4 C43 98.5(11) . . ?
N2 C23 C24 122.1(6) . . ?
N2 C23 C27 122.9(6) . . ?
C24 C23 C27 115.0(6) . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
F21 C26 F22 102.0(6) . . ?
F21 C26 C25 113.7(6) . . ?
F23 C26 F21 109.7(7) . . ?
F23 C26 F22 105.3(8) . . ?
F23 C26 C25 114.4(6) . . ?
F22 C26 C25 110.6(6) . . ?
O4 C43 H43A 113.2 . . ?
O4 C43 H43B 113.2 . . ?
H43A C43 H43B 110.5 . . ?
C44 C43 O4 92.6(13) . . ?
C44 C43 H43A 113.2 . . ?
C44 C43 H43B 113.2 . . ?
H41A C41 H41B 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C42 C41 H41A 109.5 . . ?
C42 C41 H41B 109.5 . . ?
C42 C41 H41C 109.5 . . ?
O4 C42 C41 108.0(13) . . ?
O4 C42 H42A 110.1 . . ?
O4 C42 H42B 110.1 . . ?
C41 C42 H42A 110.1 . . ?
C41 C42 H42B 110.1 . . ?
H42A C42 H42B 108.4 . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Yb1 O1 C15 C14 -39.0(8) . . . . ?
Yb1 O1 C15 C16 144.3(4) . . . . ?
Yb1 O2 C25 C24 -41.9(9) . . . . ?
Yb1 O2 C25 C26 139.2(4) . . . . ?
Yb1 O3 C35 C34 -33.3(9) . . . . ?
Yb1 O3 C35 C36 148.0(4) . . . . ?
Yb1 N1 C12 C11 10.0(6) . . . . ?
Yb1 N1 C13 C14 8.4(8) . . . . ?
Yb1 N1 C13 C17 -172.4(4) . . . . ?
Yb1 N4 C11 C12 54.8(5) . . . . ?
Yb1 N4 C31 C32 56.1(5) . . . . ?
Yb1 N4 C21 C22 57.7(5) . . . . ?
Yb1 N3 C33 C34 4.2(8) . . . . ?
Yb1 N3 C33 C37 -177.1(4) . . . . ?
Yb1 N3 C32 C31 7.7(6) . . . . ?
Yb1 N2 C22 C21 8.5(6) . . . . ?
Yb1 N2 C23 C24 -3.5(8) . . . . ?
Yb1 N2 C23 C27 174.9(4) . . . . ?
Yb1 C15 C14 C13 -24.0(6) . . . . ?
Yb1 C15 C16 F13 -146.1(5) . . . . ?
Yb1 C15 C16 F11 95.1(8) . . . . ?
Yb1 C15 C16 F12 -25.4(9) . . . . ?
Yb1 C11 C12 N1 -6.8(4) . . . . ?
Yb1 C31 C32 N3 -5.3(4) . . . . ?
Yb1 C21 C22 N2 -5.9(4) . . . . ?
Yb1 C35 C36 F33 -37.0(9) . . . . ?
Yb1 C35 C36 F32 81.2(8) . . . . ?
Yb1 C35 C36 F31 -156.4(5) . . . . ?
Yb1 C25 C26 F21 -138.4(6) . . . . ?
Yb1 C25 C26 F23 94.4(9) . . . . ?
Yb1 C25 C26 F22 -24.3(9) . . . . ?
O1 C15 C14 C13 -2.4(10) . . . . ?
O1 C15 C16 F13 -176.8(5) . . . . ?
O1 C15 C16 F11 64.3(8) . . . . ?
O1 C15 C16 F12 -56.1(7) . . . . ?
O2 C25 C26 F21 -170.4(6) . . . . ?
O2 C25 C26 F23 62.4(9) . . . . ?
O2 C25 C26 F22 -56.3(8) . . . . ?
O3 C35 C36 F33 -62.9(7) . . . . ?
O3 C35 C36 F32 55.3(8) . . . . ?
O3 C35 C36 F31 177.7(5) . . . . ?
N4 C11 C12 N1 -43.1(7) . . . . ?
N4 C31 C32 N3 -42.4(6) . . . . ?
N4 C21 C22 N2 -44.0(6) . . . . ?
C15 C14 C13 N1 17.1(9) . . . . ?
C15 C14 C13 C17 -162.2(6) . . . . ?
C14 C15 C16 F13 6.1(9) . . . . ?
C14 C15 C16 F11 -112.7(7) . . . . ?
C14 C15 C16 F12 126.8(6) . . . . ?
C11 N4 C31 Yb1 -118.0(5) . . . . ?
C11 N4 C31 C32 -61.9(6) . . . . ?
C11 N4 C21 Yb1 118.0(5) . . . . ?
C11 N4 C21 C22 175.7(4) . . . . ?
C12 N1 C13 C14 -173.3(5) . . . . ?
C12 N1 C13 C17 5.9(8) . . . . ?
C34 C35 C36 F33 118.2(6) . . . . ?
C34 C35 C36 F32 -123.6(6) . . . . ?
C34 C35 C36 F31 -1.2(9) . . . . ?
C31 N4 C11 Yb1 117.8(5) . . . . ?
C31 N4 C11 C12 172.7(5) . . . . ?
C31 N4 C21 Yb1 -118.0(5) . . . . ?
C31 N4 C21 C22 -60.3(6) . . . . ?
C33 N3 C32 C31 -173.7(5) . . . . ?
C33 C34 C35 Yb1 -19.0(7) . . . . ?
C33 C34 C35 O3 -1.3(10) . . . . ?
C33 C34 C35 C36 177.4(6) . . . . ?
C32 N3 C33 C34 -174.2(5) . . . . ?
C32 N3 C33 C37 4.5(8) . . . . ?
C16 C15 C14 C13 174.1(6) . . . . ?
C21 N4 C11 Yb1 -117.4(5) . . . . ?
C21 N4 C11 C12 -62.6(6) . . . . ?
C21 N4 C31 Yb1 117.7(5) . . . . ?
C21 N4 C31 C32 173.8(5) . . . . ?
C13 N1 C12 C11 -168.4(5) . . . . ?
C35 C34 C33 N3 15.0(10) . . . . ?
C35 C34 C33 C37 -163.9(6) . . . . ?
C22 N2 C23 C24 -178.5(5) . . . . ?
C22 N2 C23 C27 -0.1(8) . . . . ?
C24 C25 C26 F21 10.6(9) . . . . ?
C24 C25 C26 F23 -116.6(9) . . . . ?
C24 C25 C26 F22 124.7(7) . . . . ?
C25 C24 C23 N2 20.4(10) . . . . ?
C25 C24 C23 C27 -158.1(6) . . . . ?
C23 N2 C22 C21 -176.0(5) . . . . ?
C23 C24 C25 Yb1 -20.4(7) . . . . ?
C23 C24 C25 O2 2.3(11) . . . . ?
C23 C24 C25 C26 -178.8(6) . . . . ?
C43 O4 C42 C41 174.9(11) . . . . ?
C42 O4 C43 C44 173.1(10) . . . . ?

_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_dal2120
_database_code_depnum_ccdc_archive 'CCDC 2313988'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;The University of Iowa
United States of America
;
_audit_update_record             
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_audit_creation_date             2023-06-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C36 H42 F21 N4 Nd O3'
_chemical_formula_sum            'C36 H42 F21 N4 Nd O3'
_chemical_formula_weight         1121.97
_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'
N N 0.0061 0.0033 '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                   7.2329(7)
_cell_length_b                   14.5721(15)
_cell_length_c                   21.231(2)
_cell_angle_alpha                92.033(5)
_cell_angle_beta                 90.548(5)
_cell_angle_gamma                92.205(5)
_cell_volume                     2234.5(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9851
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.85
_cell_measurement_theta_min      2.416
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.910
_exptl_absorpt_coefficient_mu    1.289
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9417
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0510 before and 0.0460 after correction.
The Ratio of minimum to maximum transmission is 0.9417.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale orange'
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism-like
_exptl_crystal_F_000             1118
_exptl_crystal_size_max          0.075
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.035
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            47027
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.890
_diffrn_reflns_theta_min         2.335
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker Nonius Kappa Apex'
_diffrn_measurement_method       'CCD Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                9510
_reflns_number_total             10552
_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       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/4 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.515
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     595
_refine_ls_number_reflns         10552
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0333
_refine_ls_R_factor_gt           0.0275
_refine_ls_restrained_S_all      1.066
_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)+(0.0251P)²+1.7419P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0587
_refine_ls_wR_factor_ref         0.0618
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C21(H21A,H21B), C22(H22A,H22B), C31(H31A,
 H31B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C24(H24), C34(H34)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C27(H27A,H27B,
 H27C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C37(H37A,H37B,H37C), C38(H38A,
 H38B,H38C), C39(H39A,H39B,H39C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Nd1 Nd 0.29404(2) 0.27564(2) 0.24209(2) 0.01361(4) Uani 1 1 d . . . . .
F11 F -0.0461(2) -0.08331(9) 0.18995(7) 0.0332(3) Uani 1 1 d . . . . .
F12 F -0.18057(19) 0.04349(10) 0.16954(7) 0.0317(3) Uani 1 1 d . . . . .
F13 F -0.0762(2) -0.05827(12) 0.06990(8) 0.0479(5) Uani 1 1 d . . . . .
F14 F 0.0494(2) 0.08035(11) 0.07730(7) 0.0414(4) Uani 1 1 d . . . . .
F15 F 0.3737(2) 0.01302(12) 0.11267(9) 0.0459(4) Uani 1 1 d . . . . .
F16 F 0.2649(3) -0.05369(16) 0.02824(9) 0.0658(6) Uani 1 1 d . . . . .
F17 F 0.2548(3) -0.12321(12) 0.11608(11) 0.0581(5) Uani 1 1 d . . . . .
F21 F -0.14863(18) 0.48578(9) 0.14460(7) 0.0268(3) Uani 1 1 d . . . . .
F22 F 0.0373(2) 0.54789(10) 0.07685(7) 0.0299(3) Uani 1 1 d . . . . .
F23 F 0.0682(3) 0.55105(11) 0.24184(7) 0.0435(4) Uani 1 1 d . . . . .
F24 F 0.2749(2) 0.60263(12) 0.17565(9) 0.0490(5) Uani 1 1 d . . . . .
F25 F -0.1845(3) 0.66188(13) 0.19150(11) 0.0611(6) Uani 1 1 d . . . . .
F26 F 0.0168(3) 0.71607(12) 0.12931(10) 0.0614(6) Uani 1 1 d . . . . .
F27 F 0.0629(3) 0.73025(12) 0.22921(10) 0.0620(6) Uani 1 1 d . . . . .
F31 F 0.0291(2) 0.37475(10) 0.48882(6) 0.0319(3) Uani 1 1 d . . . . .
F32 F -0.15306(18) 0.30771(11) 0.41808(6) 0.0295(3) Uani 1 1 d . . . . .
F33 F 0.2642(2) 0.22356(14) 0.47054(10) 0.0563(5) Uani 1 1 d . . . . .
F34 F 0.0403(3) 0.15717(11) 0.41451(8) 0.0463(4) Uani 1 1 d . . . . .
F35 F -0.1942(3) 0.18839(16) 0.51434(11) 0.0706(6) Uani 1 1 d . . . . .
F36 F 0.0343(3) 0.10233(14) 0.52987(10) 0.0645(6) Uani 1 1 d . . . . .
F37 F 0.0368(4) 0.23853(16) 0.56990(9) 0.0910(9) Uani 1 1 d . . . . .
O1 O 0.1279(2) 0.14582(11) 0.20513(8) 0.0220(3) Uani 1 1 d . . . . .
O2 O 0.1295(2) 0.37996(11) 0.18747(7) 0.0212(3) Uani 1 1 d . . . . .
O3 O 0.1352(2) 0.29857(11) 0.33435(7) 0.0220(3) Uani 1 1 d . . . . .
N1 N 0.4114(2) 0.13518(13) 0.29870(9) 0.0184(4) Uani 1 1 d . . . . .
N2 N 0.4208(2) 0.28404(13) 0.13045(9) 0.0183(4) Uani 1 1 d . . . . .
N3 N 0.4329(2) 0.41955(13) 0.30208(9) 0.0184(4) Uani 1 1 d . . . . .
N4 N 0.6593(2) 0.27654(12) 0.24222(8) 0.0137(3) Uani 1 1 d . . . . .
C1 C -0.0125(3) 0.00378(16) 0.17159(12) 0.0238(5) Uani 1 1 d . . . . .
C2 C 0.0486(4) -0.00320(18) 0.10216(12) 0.0305(6) Uani 1 1 d . . . . .
C3 C 0.2396(4) -0.0428(2) 0.08996(14) 0.0388(7) Uani 1 1 d . . . . .
C4 C 0.0326(3) 0.50810(16) 0.13379(11) 0.0214(5) Uani 1 1 d . . . . .
C5 C 0.0936(4) 0.58326(17) 0.18365(12) 0.0292(5) Uani 1 1 d . . . . .
C6 C -0.0056(4) 0.67452(19) 0.18300(14) 0.0389(7) Uani 1 1 d . . . . .
C7 C 0.0267(3) 0.31666(17) 0.43717(10) 0.0222(5) Uani 1 1 d . . . . .
C8 C 0.0807(4) 0.22135(19) 0.45971(12) 0.0306(6) Uani 1 1 d . . . . .
C9 C -0.0133(5) 0.1876(2) 0.52020(14) 0.0456(8) Uani 1 1 d . . . . .
C11 C 0.7180(3) 0.20093(15) 0.28198(11) 0.0197(4) Uani 1 1 d . . . . .
H11A H 0.837231 0.218984 0.303071 0.024 Uiso 1 1 calc R U . . .
H11B H 0.737121 0.145414 0.254942 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5735(3) 0.17866(16) 0.33167(11) 0.0207(5) Uani 1 1 d . . . . .
H12A H 0.623799 0.136370 0.362443 0.025 Uiso 1 1 calc R U . . .
H12B H 0.538468 0.235584 0.354639 0.025 Uiso 1 1 calc R U . . .
C13 C 0.3618(3) 0.04897(16) 0.30140(10) 0.0199(4) Uani 1 1 d . . . . .
C14 C 0.2143(3) 0.01253(16) 0.25965(11) 0.0231(5) Uani 1 1 d . . . . .
H14 H 0.180347 -0.050742 0.262855 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1201(3) 0.05954(15) 0.21658(11) 0.0200(5) Uani 1 1 d . . . . .
C16 C 0.4536(4) -0.02099(17) 0.34486(11) 0.0269(5) Uani 1 1 d . . . . .
C17 C 0.3587(5) -0.11734(19) 0.33884(14) 0.0420(7) Uani 1 1 d . . . . .
H17A H 0.227755 -0.113424 0.349690 0.063 Uiso 1 1 calc R U . . .
H17B H 0.418843 -0.158374 0.367594 0.063 Uiso 1 1 calc R U . . .
H17C H 0.369036 -0.141542 0.295417 0.063 Uiso 1 1 calc R U . . .
C18 C 0.4327(4) 0.00962(19) 0.41475(12) 0.0342(6) Uani 1 1 d . . . . .
H18A H 0.487908 0.071662 0.421691 0.051 Uiso 1 1 calc R U . . .
H18B H 0.495711 -0.033049 0.441552 0.051 Uiso 1 1 calc R U . . .
H18C H 0.301081 0.009673 0.425345 0.051 Uiso 1 1 calc R U . . .
C19 C 0.6571(4) -0.0329(2) 0.32706(14) 0.0395(7) Uani 1 1 d . . . . .
H19A H 0.664781 -0.048794 0.281941 0.059 Uiso 1 1 calc R U . . .
H19B H 0.707965 -0.082212 0.351366 0.059 Uiso 1 1 calc R U . . .
H19C H 0.728160 0.024593 0.336528 0.059 Uiso 1 1 calc R U . . .
C21 C 0.7207(3) 0.26195(16) 0.17563(10) 0.0191(4) Uani 1 1 d . . . . .
H21A H 0.829379 0.222652 0.174678 0.023 Uiso 1 1 calc R U . . .
H21B H 0.757862 0.321787 0.157967 0.023 Uiso 1 1 calc R U . . .
C22 C 0.5642(3) 0.21621(15) 0.13573(10) 0.0192(4) Uani 1 1 d . . . . .
H22A H 0.609633 0.197909 0.093463 0.023 Uiso 1 1 calc R U . . .
H22B H 0.513992 0.160674 0.156169 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3835(3) 0.32764(16) 0.07977(10) 0.0196(4) Uani 1 1 d . . . . .
C24 C 0.2558(3) 0.40222(16) 0.08486(11) 0.0224(5) Uani 1 1 d . . . . .
H24 H 0.246263 0.440228 0.049627 0.027 Uiso 1 1 calc R U . . .
C25 C 0.1487(3) 0.42255(15) 0.13552(10) 0.0190(4) Uani 1 1 d . . . . .
C26 C 0.4626(3) 0.30547(17) 0.01323(11) 0.0250(5) Uani 1 1 d . . . . .
C27 C 0.3902(4) 0.3688(2) -0.03705(12) 0.0388(7) Uani 1 1 d . . . . .
H27A H 0.254795 0.363257 -0.038939 0.058 Uiso 1 1 calc R U . . .
H27B H 0.440556 0.350984 -0.078192 0.058 Uiso 1 1 calc R U . . .
H27C H 0.429137 0.432583 -0.026074 0.058 Uiso 1 1 calc R U . . .
C28 C 0.3970(4) 0.20736(19) -0.00709(12) 0.0340(6) Uani 1 1 d . . . . .
H28A H 0.445460 0.163921 0.022535 0.051 Uiso 1 1 calc R U . . .
H28B H 0.442144 0.192693 -0.049502 0.051 Uiso 1 1 calc R U . . .
H28C H 0.261435 0.202803 -0.007292 0.051 Uiso 1 1 calc R U . . .
C29 C 0.6752(4) 0.3189(2) 0.01270(13) 0.0330(6) Uani 1 1 d . . . . .
H29A H 0.710384 0.381543 0.027829 0.049 Uiso 1 1 calc R U . . .
H29B H 0.719798 0.309072 -0.030367 0.049 Uiso 1 1 calc R U . . .
H29C H 0.730481 0.274698 0.040286 0.049 Uiso 1 1 calc R U . . .
C31 C 0.7294(3) 0.36743(15) 0.26890(11) 0.0189(4) Uani 1 1 d . . . . .
H31A H 0.846023 0.385622 0.247870 0.023 Uiso 1 1 calc R U . . .
H31B H 0.756274 0.362411 0.314427 0.023 Uiso 1 1 calc R U . . .
C32 C 0.5882(3) 0.44066(15) 0.25983(10) 0.0189(4) Uani 1 1 d . . . . .
H32A H 0.643923 0.502400 0.270627 0.023 Uiso 1 1 calc R U . . .
H32B H 0.544596 0.439519 0.215457 0.023 Uiso 1 1 calc R U . . .
C33 C 0.3960(3) 0.46676(15) 0.35315(11) 0.0204(5) Uani 1 1 d . . . . .
C34 C 0.2574(3) 0.42885(16) 0.39536(11) 0.0227(5) Uani 1 1 d . . . . .
H34 H 0.241127 0.461306 0.434385 0.027 Uiso 1 1 calc R U . . .
C35 C 0.1492(3) 0.35164(16) 0.38431(10) 0.0191(4) Uani 1 1 d . . . . .
C36 C 0.4953(3) 0.55964(16) 0.37432(12) 0.0259(5) Uani 1 1 d . . . . .
C37 C 0.4709(4) 0.63179(17) 0.32407(13) 0.0332(6) Uani 1 1 d . . . . .
H37A H 0.546020 0.687315 0.335691 0.050 Uiso 1 1 calc R U . . .
H37B H 0.340339 0.647065 0.321378 0.050 Uiso 1 1 calc R U . . .
H37C H 0.510723 0.606955 0.283118 0.050 Uiso 1 1 calc R U . . .
C38 C 0.4138(4) 0.60143(19) 0.43515(14) 0.0408(7) Uani 1 1 d . . . . .
H38A H 0.433798 0.560472 0.469991 0.061 Uiso 1 1 calc R U . . .
H38B H 0.280773 0.608934 0.429144 0.061 Uiso 1 1 calc R U . . .
H38C H 0.474893 0.661482 0.445007 0.061 Uiso 1 1 calc R U . . .
C39 C 0.7013(4) 0.54473(19) 0.38881(13) 0.0334(6) Uani 1 1 d . . . . .
H39A H 0.711300 0.495191 0.418543 0.050 Uiso 1 1 calc R U . . .
H39B H 0.758778 0.601513 0.407393 0.050 Uiso 1 1 calc R U . . .
H39C H 0.764609 0.528025 0.349685 0.050 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O1 2.3108(15) . ?
Nd1 O2 2.3045(15) . ?
Nd1 O3 2.3012(15) . ?
Nd1 N1 2.5775(19) . ?
Nd1 N2 2.5547(18) . ?
Nd1 N3 2.5794(18) . ?
Nd1 N4 2.6411(17) . ?
F11 C1 1.354(3) . ?
F12 C1 1.367(3) . ?
F13 C2 1.349(3) . ?
F14 C2 1.344(3) . ?
F15 C3 1.318(3) . ?
F16 C3 1.330(3) . ?
F17 C3 1.322(4) . ?
F21 C4 1.362(3) . ?
F22 C4 1.359(3) . ?
F23 C5 1.349(3) . ?
F24 C5 1.345(3) . ?
F25 C6 1.315(4) . ?
F26 C6 1.318(3) . ?
F27 C6 1.331(3) . ?
F31 C7 1.361(3) . ?
F32 C7 1.358(3) . ?
F33 C8 1.343(3) . ?
F34 C8 1.338(3) . ?
F35 C9 1.313(4) . ?
F36 C9 1.325(4) . ?
F37 C9 1.309(4) . ?
O1 C15 1.288(3) . ?
O2 C25 1.291(3) . ?
O3 C35 1.291(3) . ?
N1 C12 1.470(3) . ?
N1 C13 1.297(3) . ?
N2 C22 1.466(3) . ?
N2 C23 1.300(3) . ?
N3 C32 1.474(3) . ?
N3 C33 1.299(3) . ?
N4 C11 1.484(3) . ?
N4 C21 1.497(3) . ?
N4 C31 1.491(3) . ?
C1 C2 1.544(4) . ?
C1 C15 1.537(3) . ?
C2 C3 1.538(4) . ?
C4 C5 1.545(3) . ?
C4 C25 1.531(3) . ?
C5 C6 1.535(4) . ?
C7 C8 1.548(4) . ?
C7 C35 1.526(3) . ?
C8 C9 1.546(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.526(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.453(3) . ?
C13 C16 1.562(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.355(3) . ?
C16 C17 1.539(4) . ?
C16 C18 1.545(3) . ?
C16 C19 1.538(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.526(3) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.455(3) . ?
C23 C26 1.557(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.362(3) . ?
C26 C27 1.537(4) . ?
C26 C28 1.535(4) . ?
C26 C29 1.543(3) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C32 1.521(3) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C33 C34 1.457(3) . ?
C33 C36 1.557(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.358(3) . ?
C36 C37 1.538(4) . ?
C36 C38 1.540(3) . ?
C36 C39 1.544(4) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Nd1 N1 71.20(6) . . ?
O1 Nd1 N2 85.89(6) . . ?
O1 Nd1 N3 168.34(6) . . ?
O1 Nd1 N4 119.31(5) . . ?
O2 Nd1 O1 96.57(6) . . ?
O2 Nd1 N1 166.90(6) . . ?
O2 Nd1 N2 71.06(6) . . ?
O2 Nd1 N3 84.25(6) . . ?
O2 Nd1 N4 122.30(5) . . ?
O3 Nd1 O1 97.58(6) . . ?
O3 Nd1 O2 94.27(6) . . ?
O3 Nd1 N1 83.04(6) . . ?
O3 Nd1 N2 165.25(6) . . ?
O3 Nd1 N3 70.76(6) . . ?
O3 Nd1 N4 120.77(5) . . ?
N1 Nd1 N3 106.76(6) . . ?
N1 Nd1 N4 69.39(5) . . ?
N2 Nd1 N1 111.58(6) . . ?
N2 Nd1 N3 105.29(6) . . ?
N2 Nd1 N4 68.58(6) . . ?
N3 Nd1 N4 69.03(5) . . ?
C15 O1 Nd1 136.98(14) . . ?
C25 O2 Nd1 136.31(14) . . ?
C35 O3 Nd1 137.64(14) . . ?
C12 N1 Nd1 99.36(13) . . ?
C13 N1 Nd1 136.13(15) . . ?
C13 N1 C12 124.50(19) . . ?
C22 N2 Nd1 98.18(12) . . ?
C23 N2 Nd1 136.80(15) . . ?
C23 N2 C22 125.00(19) . . ?
C32 N3 Nd1 98.72(12) . . ?
C33 N3 Nd1 136.53(15) . . ?
C33 N3 C32 124.75(19) . . ?
C11 N4 Nd1 107.84(12) . . ?
C11 N4 C21 110.97(17) . . ?
C11 N4 C31 110.92(17) . . ?
C21 N4 Nd1 108.06(12) . . ?
C31 N4 Nd1 107.88(12) . . ?
C31 N4 C21 111.02(16) . . ?
F11 C1 F12 106.17(18) . . ?
F11 C1 C2 106.74(19) . . ?
F11 C1 C15 112.8(2) . . ?
F12 C1 C2 104.6(2) . . ?
F12 C1 C15 110.27(18) . . ?
C15 C1 C2 115.49(19) . . ?
F13 C2 C1 108.1(2) . . ?
F13 C2 C3 106.8(2) . . ?
F14 C2 F13 108.3(2) . . ?
F14 C2 C1 109.7(2) . . ?
F14 C2 C3 107.3(2) . . ?
C3 C2 C1 116.4(2) . . ?
F15 C3 F16 107.6(2) . . ?
F15 C3 F17 108.1(3) . . ?
F15 C3 C2 111.3(2) . . ?
F16 C3 C2 109.6(3) . . ?
F17 C3 F16 108.7(2) . . ?
F17 C3 C2 111.4(2) . . ?
F21 C4 C5 107.01(19) . . ?
F21 C4 C25 110.50(18) . . ?
F22 C4 F21 106.16(17) . . ?
F22 C4 C5 106.92(19) . . ?
F22 C4 C25 112.61(19) . . ?
C25 C4 C5 113.23(19) . . ?
F23 C5 C4 109.5(2) . . ?
F23 C5 C6 105.8(2) . . ?
F24 C5 F23 108.9(2) . . ?
F24 C5 C4 107.7(2) . . ?
F24 C5 C6 107.3(2) . . ?
C6 C5 C4 117.4(2) . . ?
F25 C6 F26 107.5(3) . . ?
F25 C6 F27 108.6(3) . . ?
F25 C6 C5 111.3(2) . . ?
F26 C6 F27 108.2(2) . . ?
F26 C6 C5 112.0(2) . . ?
F27 C6 C5 109.1(2) . . ?
F31 C7 C8 107.14(19) . . ?
F31 C7 C35 112.89(19) . . ?
F32 C7 F31 105.83(18) . . ?
F32 C7 C8 106.54(19) . . ?
F32 C7 C35 110.97(18) . . ?
C35 C7 C8 112.99(19) . . ?
F33 C8 C7 108.4(2) . . ?
F33 C8 C9 107.1(2) . . ?
F34 C8 F33 108.4(2) . . ?
F34 C8 C7 109.7(2) . . ?
F34 C8 C9 106.3(2) . . ?
C9 C8 C7 116.6(2) . . ?
F35 C9 F36 108.6(3) . . ?
F35 C9 C8 110.6(3) . . ?
F36 C9 C8 109.1(3) . . ?
F37 C9 F35 108.4(3) . . ?
F37 C9 F36 108.0(3) . . ?
F37 C9 C8 112.0(3) . . ?
N4 C11 H11A 109.4 . . ?
N4 C11 H11B 109.4 . . ?
N4 C11 C12 111.22(18) . . ?
H11A C11 H11B 108.0 . . ?
C12 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N1 C12 C11 107.45(18) . . ?
N1 C12 H12A 110.2 . . ?
N1 C12 H12B 110.2 . . ?
C11 C12 H12A 110.2 . . ?
C11 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
N1 C13 C14 118.5(2) . . ?
N1 C13 C16 124.9(2) . . ?
C14 C13 C16 116.5(2) . . ?
C13 C14 H14 116.7 . . ?
C15 C14 C13 126.7(2) . . ?
C15 C14 H14 116.7 . . ?
O1 C15 C1 112.6(2) . . ?
O1 C15 C14 130.0(2) . . ?
C14 C15 C1 117.3(2) . . ?
C17 C16 C13 112.4(2) . . ?
C17 C16 C18 105.2(2) . . ?
C18 C16 C13 110.1(2) . . ?
C19 C16 C13 110.7(2) . . ?
C19 C16 C17 106.3(2) . . ?
C19 C16 C18 112.1(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N4 C21 H21A 109.6 . . ?
N4 C21 H21B 109.6 . . ?
N4 C21 C22 110.15(17) . . ?
H21A C21 H21B 108.1 . . ?
C22 C21 H21A 109.6 . . ?
C22 C21 H21B 109.6 . . ?
N2 C22 C21 106.74(18) . . ?
N2 C22 H22A 110.4 . . ?
N2 C22 H22B 110.4 . . ?
C21 C22 H22A 110.4 . . ?
C21 C22 H22B 110.4 . . ?
H22A C22 H22B 108.6 . . ?
N2 C23 C24 118.0(2) . . ?
N2 C23 C26 125.1(2) . . ?
C24 C23 C26 116.9(2) . . ?
C23 C24 H24 117.0 . . ?
C25 C24 C23 126.0(2) . . ?
C25 C24 H24 117.0 . . ?
O2 C25 C4 112.34(19) . . ?
O2 C25 C24 129.4(2) . . ?
C24 C25 C4 118.3(2) . . ?
C27 C26 C23 112.5(2) . . ?
C27 C26 C29 105.6(2) . . ?
C28 C26 C23 108.2(2) . . ?
C28 C26 C27 106.5(2) . . ?
C28 C26 C29 112.6(2) . . ?
C29 C26 C23 111.42(19) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C26 C29 H29A 109.5 . . ?
C26 C29 H29B 109.5 . . ?
C26 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N4 C31 H31A 109.4 . . ?
N4 C31 H31B 109.4 . . ?
N4 C31 C32 110.99(17) . . ?
H31A C31 H31B 108.0 . . ?
C32 C31 H31A 109.4 . . ?
C32 C31 H31B 109.4 . . ?
N3 C32 C31 106.86(18) . . ?
N3 C32 H32A 110.3 . . ?
N3 C32 H32B 110.3 . . ?
C31 C32 H32A 110.3 . . ?
C31 C32 H32B 110.3 . . ?
H32A C32 H32B 108.6 . . ?
N3 C33 C34 118.1(2) . . ?
N3 C33 C36 124.7(2) . . ?
C34 C33 C36 117.10(19) . . ?
C33 C34 H34 116.8 . . ?
C35 C34 C33 126.3(2) . . ?
C35 C34 H34 116.8 . . ?
O3 C35 C7 111.76(19) . . ?
O3 C35 C34 129.5(2) . . ?
C34 C35 C7 118.8(2) . . ?
C37 C36 C33 110.5(2) . . ?
C37 C36 C38 105.5(2) . . ?
C37 C36 C39 111.9(2) . . ?
C38 C36 C33 112.5(2) . . ?
C38 C36 C39 106.3(2) . . ?
C39 C36 C33 110.0(2) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C36 C38 H38A 109.5 . . ?
C36 C38 H38B 109.5 . . ?
C36 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C36 C39 H39A 109.5 . . ?
C36 C39 H39B 109.5 . . ?
C36 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Nd1 O1 C15 C1 -175.49(15) . . . . ?
Nd1 O1 C15 C14 1.9(4) . . . . ?
Nd1 O2 C25 C4 -159.95(15) . . . . ?
Nd1 O2 C25 C24 19.3(4) . . . . ?
Nd1 O3 C35 C7 -165.10(16) . . . . ?
Nd1 O3 C35 C34 13.0(4) . . . . ?
Nd1 N1 C12 C11 -70.12(17) . . . . ?
Nd1 N1 C13 C14 7.1(3) . . . . ?
Nd1 N1 C13 C16 -175.21(16) . . . . ?
Nd1 N2 C22 C21 -74.20(16) . . . . ?
Nd1 N2 C23 C24 11.1(3) . . . . ?
Nd1 N2 C23 C26 -167.88(16) . . . . ?
Nd1 N3 C32 C31 -71.77(16) . . . . ?
Nd1 N3 C33 C34 9.9(3) . . . . ?
Nd1 N3 C33 C36 -172.84(16) . . . . ?
Nd1 N4 C11 C12 -26.5(2) . . . . ?
Nd1 N4 C21 C22 -21.7(2) . . . . ?
Nd1 N4 C31 C32 -25.23(19) . . . . ?
F11 C1 C2 F13 50.2(3) . . . . ?
F11 C1 C2 F14 168.08(19) . . . . ?
F11 C1 C2 C3 -69.9(3) . . . . ?
F11 C1 C15 O1 -169.19(19) . . . . ?
F11 C1 C15 C14 13.1(3) . . . . ?
F12 C1 C2 F13 -62.1(2) . . . . ?
F12 C1 C2 F14 55.8(2) . . . . ?
F12 C1 C2 C3 177.9(2) . . . . ?
F12 C1 C15 O1 -50.7(3) . . . . ?
F12 C1 C15 C14 131.6(2) . . . . ?
F13 C2 C3 F15 171.6(2) . . . . ?
F13 C2 C3 F16 52.7(3) . . . . ?
F13 C2 C3 F17 -67.6(3) . . . . ?
F14 C2 C3 F15 55.7(3) . . . . ?
F14 C2 C3 F16 -63.2(3) . . . . ?
F14 C2 C3 F17 176.5(2) . . . . ?
F21 C4 C5 F23 58.5(2) . . . . ?
F21 C4 C5 F24 176.84(19) . . . . ?
F21 C4 C5 C6 -62.0(3) . . . . ?
F21 C4 C25 O2 -55.1(2) . . . . ?
F21 C4 C25 C24 125.5(2) . . . . ?
F22 C4 C5 F23 171.94(19) . . . . ?
F22 C4 C5 F24 -69.8(2) . . . . ?
F22 C4 C5 C6 51.4(3) . . . . ?
F22 C4 C25 O2 -173.66(18) . . . . ?
F22 C4 C25 C24 7.0(3) . . . . ?
F23 C5 C6 F25 -62.9(3) . . . . ?
F23 C5 C6 F26 176.7(2) . . . . ?
F23 C5 C6 F27 56.9(3) . . . . ?
F24 C5 C6 F25 -179.1(2) . . . . ?
F24 C5 C6 F26 60.5(3) . . . . ?
F24 C5 C6 F27 -59.3(3) . . . . ?
F31 C7 C8 F33 -75.8(2) . . . . ?
F31 C7 C8 F34 165.98(19) . . . . ?
F31 C7 C8 C9 45.1(3) . . . . ?
F31 C7 C35 O3 -175.67(19) . . . . ?
F31 C7 C35 C34 6.0(3) . . . . ?
F32 C7 C8 F33 171.33(19) . . . . ?
F32 C7 C8 F34 53.1(2) . . . . ?
F32 C7 C8 C9 -67.8(3) . . . . ?
F32 C7 C35 O3 -57.1(3) . . . . ?
F32 C7 C35 C34 124.6(2) . . . . ?
F33 C8 C9 F35 176.6(2) . . . . ?
F33 C8 C9 F36 -64.0(3) . . . . ?
F33 C8 C9 F37 55.6(4) . . . . ?
F34 C8 C9 F35 -67.6(3) . . . . ?
F34 C8 C9 F36 51.8(3) . . . . ?
F34 C8 C9 F37 171.3(3) . . . . ?
N1 C13 C14 C15 0.4(4) . . . . ?
N1 C13 C16 C17 178.0(2) . . . . ?
N1 C13 C16 C18 61.1(3) . . . . ?
N1 C13 C16 C19 -63.4(3) . . . . ?
N2 C23 C24 C25 -10.6(4) . . . . ?
N2 C23 C26 C27 179.3(2) . . . . ?
N2 C23 C26 C28 62.0(3) . . . . ?
N2 C23 C26 C29 -62.2(3) . . . . ?
N3 C33 C34 C35 -6.1(4) . . . . ?
N3 C33 C36 C37 59.3(3) . . . . ?
N3 C33 C36 C38 177.0(2) . . . . ?
N3 C33 C36 C39 -64.8(3) . . . . ?
N4 C11 C12 N1 70.0(2) . . . . ?
N4 C21 C22 N2 68.6(2) . . . . ?
N4 C31 C32 N3 70.1(2) . . . . ?
C1 C2 C3 F15 -67.6(3) . . . . ?
C1 C2 C3 F16 173.5(2) . . . . ?
C1 C2 C3 F17 53.2(3) . . . . ?
C2 C1 C15 O1 67.7(3) . . . . ?
C2 C1 C15 C14 -110.1(3) . . . . ?
C4 C5 C6 F25 59.5(3) . . . . ?
C4 C5 C6 F26 -60.9(3) . . . . ?
C4 C5 C6 F27 179.3(2) . . . . ?
C5 C4 C25 O2 64.9(2) . . . . ?
C5 C4 C25 C24 -114.5(2) . . . . ?
C7 C8 C9 F35 55.0(3) . . . . ?
C7 C8 C9 F36 174.4(2) . . . . ?
C7 C8 C9 F37 -66.0(4) . . . . ?
C8 C7 C35 O3 62.5(3) . . . . ?
C8 C7 C35 C34 -115.8(2) . . . . ?
C11 N4 C21 C22 96.4(2) . . . . ?
C11 N4 C31 C32 -143.13(18) . . . . ?
C12 N1 C13 C14 -171.5(2) . . . . ?
C12 N1 C13 C16 6.2(3) . . . . ?
C13 N1 C12 C11 108.9(2) . . . . ?
C13 C14 C15 O1 -5.2(4) . . . . ?
C13 C14 C15 C1 172.1(2) . . . . ?
C14 C13 C16 C17 -4.3(3) . . . . ?
C14 C13 C16 C18 -121.2(2) . . . . ?
C14 C13 C16 C19 114.3(2) . . . . ?
C15 C1 C2 F13 176.5(2) . . . . ?
C15 C1 C2 F14 -65.6(3) . . . . ?
C15 C1 C2 C3 56.4(3) . . . . ?
C16 C13 C14 C15 -177.5(2) . . . . ?
C21 N4 C11 C12 -144.62(18) . . . . ?
C21 N4 C31 C32 93.0(2) . . . . ?
C22 N2 C23 C24 -171.2(2) . . . . ?
C22 N2 C23 C26 9.8(3) . . . . ?
C23 N2 C22 C21 107.4(2) . . . . ?
C23 C24 C25 O2 -3.4(4) . . . . ?
C23 C24 C25 C4 175.8(2) . . . . ?
C24 C23 C26 C27 0.3(3) . . . . ?
C24 C23 C26 C28 -117.0(2) . . . . ?
C24 C23 C26 C29 118.8(2) . . . . ?
C25 C4 C5 F23 -63.5(3) . . . . ?
C25 C4 C5 F24 54.8(3) . . . . ?
C25 C4 C5 C6 176.0(2) . . . . ?
C26 C23 C24 C25 168.4(2) . . . . ?
C31 N4 C11 C12 91.5(2) . . . . ?
C31 N4 C21 C22 -139.78(18) . . . . ?
C32 N3 C33 C34 -170.0(2) . . . . ?
C32 N3 C33 C36 7.3(4) . . . . ?
C33 N3 C32 C31 108.1(2) . . . . ?
C33 C34 C35 O3 -4.7(4) . . . . ?
C33 C34 C35 C7 173.3(2) . . . . ?
C34 C33 C36 C37 -123.4(2) . . . . ?
C34 C33 C36 C38 -5.7(3) . . . . ?
C34 C33 C36 C39 112.5(2) . . . . ?
C35 C7 C8 F33 49.2(3) . . . . ?
C35 C7 C8 F34 -69.1(3) . . . . ?
C35 C7 C8 C9 170.1(2) . . . . ?
C36 C33 C34 C35 176.5(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
