#------------------------------------------------------------------------------
#$Date: 2024-03-04 08:36:53 +0200 (Mon, 04 Mar 2024) $
#$Revision: 290060 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/53/7715362.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7715362
loop_
_publ_author_name
'Zgrabik, Joshua C.'
'Bhuniya, Balaka'
'Branstad Phillips, Thomas'
'Barroso, Jorge'
'Vlaisavljevich, Bess'
'Daly, Scott R.'
_publ_section_title
;
 Volatile lanthanide complexes with fluorinated heptadentate ligands.
;
_journal_issue                   7
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              2998
_journal_page_last               3009
_journal_paper_doi               10.1039/d3dt04198k
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C30 H35 F21 N4 O3'
_chemical_formula_sum            'C30 H35 F21 N4 O3'
_chemical_formula_weight         898.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2023-12-12
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2023-12-12 deposited with the CCDC.	2024-01-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.461(5)
_cell_angle_beta                 98.735(5)
_cell_angle_gamma                115.475(5)
_cell_formula_units_Z            2
_cell_length_a                   11.9357(12)
_cell_length_b                   13.2583(13)
_cell_length_c                   14.1754(14)
_cell_measurement_reflns_used    2576
_cell_measurement_temperature    150.00
_cell_measurement_theta_max      26.944
_cell_measurement_theta_min      2.323
_cell_volume                     1899.7(4)
_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)'
_diffrn_ambient_temperature      150.15
_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_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_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
_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_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.571
_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
_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_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0465
_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
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5152
_reflns_number_total             7792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3dt04198k2.cif
_cod_data_source_block           dal2123
_cod_original_cell_volume        1899.7(3)
_cod_database_code               7715362
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.978
_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)
;
_olex2_exptl_crystal_mounting_method 'MiTeGen 100 micron MicroLoop'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
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'
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_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_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) . . . . ?
