# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_170728d1_a
_database_code_depnum_ccdc_archive 'CCDC 1914680'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H20 F20 Ni2 O10'
_chemical_formula_sum            'C38 H20 F20 Ni2 O10'
_chemical_formula_weight         1133.96

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'
Ni Ni 0.3393 1.1124 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.0454(6)
_cell_length_b                   7.0154(3)
_cell_length_c                   20.9702(10)
_cell_angle_alpha                90
_cell_angle_beta                 105.948(2)
_cell_angle_gamma                90
_cell_volume                     1986.75(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    103
_cell_measurement_reflns_used    9984
_cell_measurement_theta_min      2.8340
_cell_measurement_theta_max      27.1130

_exptl_crystal_description       prismatic
_exptl_crystal_colour            green
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    1.102
_shelx_estimated_absorpt_T_min   0.794
_shelx_estimated_absorpt_T_max   0.912
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            25815
_diffrn_reflns_av_unetI/netI     0.0264
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.017
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3514
_reflns_number_gt                3219
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.7 RC2'
_computing_cell_refinement       'APEX3 v2017.7-RC3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 853)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0167P)²+1.9573P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3514
_refine_ls_number_parameters     329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0608
_refine_ls_wR_factor_gt          0.0589
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75429(16) -0.0224(3) 0.40601(11) 0.0229(5) Uani 1 1 d . . . . .
C2 C 0.80828(18) -0.1709(3) 0.39029(12) 0.0285(5) Uani 1 1 d . . . . .
C3 C 0.88896(18) -0.2417(3) 0.43752(12) 0.0280(5) Uani 1 1 d . . . . .
C4 C 0.91607(16) -0.1608(3) 0.49927(12) 0.0246(5) Uani 1 1 d . . . . .
C5 C 0.86219(16) -0.0104(3) 0.51388(11) 0.0198(5) Uani 1 1 d . . . . .
C6 C 0.77904(15) 0.0614(3) 0.46861(11) 0.0169(4) Uani 1 1 d . . . . .
C7 C 0.71031(15) 0.2041(3) 0.48601(10) 0.0172(4) Uani 1 1 d . . . . .
C8 C 0.74727(15) 0.3695(3) 0.51824(11) 0.0179(4) Uani 1 1 d . . . . .
H8 H 0.816188 0.392475 0.526110 0.021 Uiso 1 1 calc R U . . .
C9 C 0.69056(14) 0.5104(3) 0.54101(10) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.73951(15) 0.6612(3) 0.58177(11) 0.0178(4) Uani 1 1 d . . . . .
H10 H 0.809443 0.666849 0.590106 0.021 Uiso 1 1 calc R U . . .
C11 C 0.69581(15) 0.8020(3) 0.61087(10) 0.0170(4) Uani 1 1 d . . . . .
C12 C 0.76184(15) 0.9235(3) 0.66461(10) 0.0170(4) Uani 1 1 d . . . . .
C13 C 0.73760(15) 1.1097(3) 0.67676(10) 0.0177(4) Uani 1 1 d . . . . .
C14 C 0.79294(16) 1.2194(3) 0.72803(11) 0.0210(5) Uani 1 1 d . . . . .
C15 C 0.87858(16) 1.1471(3) 0.76971(11) 0.0219(5) Uani 1 1 d . . . . .
C16 C 0.90678(15) 0.9645(3) 0.75969(11) 0.0210(5) Uani 1 1 d . . . . .
C17 C 0.84881(15) 0.8561(3) 0.70869(11) 0.0183(4) Uani 1 1 d . . . . .
C18 C 0.49534(19) 0.4445(4) 0.31927(12) 0.0335(6) Uani 1 1 d . . . . .
H18A H 0.437932 0.530416 0.302753 0.040 Uiso 1 1 calc R U . . .
H18B H 0.471346 0.311598 0.311183 0.040 Uiso 1 1 calc R U . . .
C19 C 0.5691(2) 0.4815(5) 0.28191(14) 0.0477(8) Uani 1 1 d . . . . .
H19A H 0.591930 0.613788 0.288964 0.072 Uiso 1 1 calc R U . . .
H19B H 0.538488 0.459912 0.234526 0.072 Uiso 1 1 calc R U . . .
H19C H 0.625550 0.395163 0.297570 0.072 Uiso 1 1 calc R U . . .
F1 F 0.67611(10) 0.0402(2) 0.35827(6) 0.0339(3) Uani 1 1 d . . . . .
F2 F 0.78193(12) -0.2463(2) 0.32911(7) 0.0446(4) Uani 1 1 d . . . . .
F3 F 0.94016(12) -0.3883(2) 0.42329(8) 0.0440(4) Uani 1 1 d . . . . .
F4 F 0.99387(10) -0.2310(2) 0.54582(7) 0.0369(4) Uani 1 1 d . . . . .
F5 F 0.89204(9) 0.05986(19) 0.57589(6) 0.0277(3) Uani 1 1 d . . . . .
F6 F 0.65734(9) 1.19671(17) 0.63738(6) 0.0240(3) Uani 1 1 d . . . . .
F7 F 0.76302(10) 1.39573(18) 0.73783(7) 0.0292(3) Uani 1 1 d . . . . .
F8 F 0.93209(10) 1.2532(2) 0.81967(7) 0.0323(3) Uani 1 1 d . . . . .
F9 F 0.98834(9) 0.8880(2) 0.80042(6) 0.0294(3) Uani 1 1 d . . . . .
F10 F 0.87982(9) 0.67656(18) 0.70542(6) 0.0259(3) Uani 1 1 d . . . . .
Ni1 Ni 0.50345(2) 0.31266(4) 0.46398(2) 0.01498(8) Uani 1 1 d . . . . .
O1 O 0.61938(10) 0.14607(19) 0.46887(7) 0.0183(3) Uani 1 1 d . . . . .
O2 O 0.59523(10) 0.49354(19) 0.52641(7) 0.0167(3) Uani 1 1 d . . . . .
O3 O 0.60279(10) 0.84032(19) 0.59833(7) 0.0177(3) Uani 1 1 d . . . . .
O4 O 0.53585(12) 0.4732(2) 0.38904(8) 0.0226(4) Uani 1 1 d . . . . .
O5 O 0.47810(12) 0.1758(2) 0.54858(8) 0.0186(3) Uani 1 1 d . . . . .
H4 H 0.5360(19) 0.577(4) 0.3982(13) 0.029(8) Uiso 1 1 d . . . . .
H5A H 0.526(2) 0.124(5) 0.5699(16) 0.051(10) Uiso 1 1 d . . . . .
H5B H 0.433(2) 0.090(4) 0.5397(14) 0.044(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.340(3) . ?
C1 C2 1.381(3) . ?
C1 C6 1.393(3) . ?
C2 F2 1.343(3) . ?
C2 C3 1.377(3) . ?
C3 F3 1.335(3) . ?
C3 C4 1.368(3) . ?
C4 F4 1.343(3) . ?
C4 C5 1.381(3) . ?
C5 F5 1.345(2) . ?
C5 C6 1.382(3) . ?
C6 C7 1.504(3) . ?
C7 O1 1.294(2) . ?
C7 C8 1.371(3) . ?
C8 C9 1.431(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.294(2) . ?
C9 C10 1.414(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 O3 1.288(2) . ?
C11 C12 1.511(3) . ?
C12 C13 1.391(3) . ?
C12 C17 1.396(3) . ?
C13 F6 1.347(2) . ?
C13 C14 1.376(3) . ?
C14 F7 1.340(2) . ?
C14 C15 1.375(3) . ?
C15 F8 1.336(2) . ?
C15 C16 1.374(3) . ?
C16 F9 1.339(2) . ?
C16 C17 1.381(3) . ?
C17 F10 1.341(2) . ?
C18 O4 1.431(3) . ?
C18 C19 1.483(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
Ni1 O1 1.9839(14) . ?
Ni1 O2 1.9909(13) 3_666 ?
Ni1 O3 2.0036(14) 3_666 ?
Ni1 O2 2.0146(14) . ?
Ni1 O4 2.0829(16) . ?
Ni1 O5 2.1314(16) . ?
O4 H4 0.75(3) . ?
O5 H5A 0.79(3) . ?
O5 H5B 0.86(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 117.4(2) . . ?
F1 C1 C6 120.44(19) . . ?
C2 C1 C6 122.2(2) . . ?
F2 C2 C3 120.1(2) . . ?
F2 C2 C1 120.0(2) . . ?
C3 C2 C1 119.9(2) . . ?
F3 C3 C4 120.3(2) . . ?
F3 C3 C2 120.3(2) . . ?
C4 C3 C2 119.4(2) . . ?
F4 C4 C3 119.7(2) . . ?
F4 C4 C5 120.3(2) . . ?
C3 C4 C5 120.0(2) . . ?
F5 C5 C4 116.8(2) . . ?
F5 C5 C6 120.70(18) . . ?
C4 C5 C6 122.5(2) . . ?
C5 C6 C1 116.01(19) . . ?
C5 C6 C7 123.62(19) . . ?
C1 C6 C7 119.96(19) . . ?
O1 C7 C8 127.91(19) . . ?
O1 C7 C6 111.93(17) . . ?
C8 C7 C6 120.12(18) . . ?
C7 C8 C9 125.38(19) . . ?
C7 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
O2 C9 C10 120.72(18) . . ?
O2 C9 C8 119.49(18) . . ?
C10 C9 C8 119.72(18) . . ?
C11 C10 C9 126.68(19) . . ?
C11 C10 H10 116.7 . . ?
C9 C10 H10 116.7 . . ?
O3 C11 C10 127.17(19) . . ?
O3 C11 C12 114.52(18) . . ?
C10 C11 C12 118.29(18) . . ?
C13 C12 C17 114.22(19) . . ?
C13 C12 C11 122.37(19) . . ?
C17 C12 C11 123.31(19) . . ?
F6 C13 C14 115.08(19) . . ?
F6 C13 C12 121.26(18) . . ?
C14 C13 C12 123.7(2) . . ?
F7 C14 C15 119.95(19) . . ?
F7 C14 C13 120.2(2) . . ?
C15 C14 C13 119.9(2) . . ?
F8 C15 C16 121.1(2) . . ?
F8 C15 C14 119.9(2) . . ?
C16 C15 C14 119.0(2) . . ?
F9 C16 C15 120.55(19) . . ?
F9 C16 C17 119.5(2) . . ?
C15 C16 C17 119.9(2) . . ?
F10 C17 C16 115.23(19) . . ?
F10 C17 C12 121.43(19) . . ?
C16 C17 C12 123.3(2) . . ?
O4 C18 C19 112.1(2) . . ?
O4 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
O4 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O1 Ni1 O2 168.92(6) . 3_666 ?
O1 Ni1 O3 99.89(6) . 3_666 ?
O2 Ni1 O3 91.00(6) 3_666 3_666 ?
O1 Ni1 O2 88.16(6) . . ?
O2 Ni1 O2 80.97(6) 3_666 . ?
O3 Ni1 O2 171.94(6) 3_666 . ?
O1 Ni1 O4 90.64(6) . . ?
O2 Ni1 O4 90.55(6) 3_666 . ?
O3 Ni1 O4 94.33(6) 3_666 . ?
O2 Ni1 O4 85.19(6) . . ?
O1 Ni1 O5 90.81(6) . . ?
O2 Ni1 O5 86.74(6) 3_666 . ?
O3 Ni1 O5 92.11(6) 3_666 . ?
O2 Ni1 O5 88.07(6) . . ?
O4 Ni1 O5 173.06(6) . . ?
C7 O1 Ni1 124.22(13) . . ?
C9 O2 Ni1 128.13(13) . 3_666 ?
C9 O2 Ni1 130.31(13) . . ?
Ni1 O2 Ni1 99.03(6) 3_666 . ?
C11 O3 Ni1 123.59(13) . 3_666 ?
C18 O4 Ni1 125.97(14) . . ?
C18 O4 H4 112(2) . . ?
Ni1 O4 H4 108(2) . . ?
Ni1 O5 H5A 111(2) . . ?
Ni1 O5 H5B 114.7(19) . . ?
H5A O5 H5B 106(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 0.2(3) . . . . ?
C6 C1 C2 F2 -179.6(2) . . . . ?
F1 C1 C2 C3 -179.6(2) . . . . ?
C6 C1 C2 C3 0.6(4) . . . . ?
F2 C2 C3 F3 -1.5(4) . . . . ?
C1 C2 C3 F3 178.4(2) . . . . ?
F2 C2 C3 C4 178.7(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
F3 C3 C4 F4 -0.8(3) . . . . ?
C2 C3 C4 F4 179.1(2) . . . . ?
F3 C3 C4 C5 -179.4(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
F4 C4 C5 F5 0.3(3) . . . . ?
C3 C4 C5 F5 178.9(2) . . . . ?
F4 C4 C5 C6 -177.12(19) . . . . ?
C3 C4 C5 C6 1.5(3) . . . . ?
F5 C5 C6 C1 -179.54(19) . . . . ?
C4 C5 C6 C1 -2.3(3) . . . . ?
F5 C5 C6 C7 -6.9(3) . . . . ?
C4 C5 C6 C7 170.4(2) . . . . ?
F1 C1 C6 C5 -178.55(19) . . . . ?
C2 C1 C6 C5 1.2(3) . . . . ?
F1 C1 C6 C7 8.5(3) . . . . ?
C2 C1 C6 C7 -171.7(2) . . . . ?
C5 C6 C7 O1 -125.9(2) . . . . ?
C1 C6 C7 O1 46.5(3) . . . . ?
C5 C6 C7 C8 52.1(3) . . . . ?
C1 C6 C7 C8 -135.5(2) . . . . ?
O1 C7 C8 C9 1.7(4) . . . . ?
C6 C7 C8 C9 -176.0(2) . . . . ?
C7 C8 C9 O2 -6.0(3) . . . . ?
C7 C8 C9 C10 171.1(2) . . . . ?
O2 C9 C10 C11 0.9(3) . . . . ?
C8 C9 C10 C11 -176.0(2) . . . . ?
C9 C10 C11 O3 -11.8(4) . . . . ?
C9 C10 C11 C12 166.5(2) . . . . ?
O3 C11 C12 C13 -29.9(3) . . . . ?
C10 C11 C12 C13 151.6(2) . . . . ?
O3 C11 C12 C17 146.2(2) . . . . ?
C10 C11 C12 C17 -32.3(3) . . . . ?
C17 C12 C13 F6 178.11(18) . . . . ?
C11 C12 C13 F6 -5.5(3) . . . . ?
C17 C12 C13 C14 -0.8(3) . . . . ?
C11 C12 C13 C14 175.61(19) . . . . ?
F6 C13 C14 F7 3.2(3) . . . . ?
C12 C13 C14 F7 -177.83(19) . . . . ?
F6 C13 C14 C15 -177.48(18) . . . . ?
C12 C13 C14 C15 1.5(3) . . . . ?
F7 C14 C15 F8 -0.4(3) . . . . ?
C13 C14 C15 F8 -179.71(19) . . . . ?
F7 C14 C15 C16 178.57(19) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
F8 C15 C16 F9 0.7(3) . . . . ?
C14 C15 C16 F9 -178.23(19) . . . . ?
F8 C15 C16 C17 178.37(19) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
F9 C16 C17 F10 1.3(3) . . . . ?
C15 C16 C17 F10 -176.41(18) . . . . ?
F9 C16 C17 C12 178.97(18) . . . . ?
C15 C16 C17 C12 1.3(3) . . . . ?
C13 C12 C17 F10 176.97(18) . . . . ?
C11 C12 C17 F10 0.6(3) . . . . ?
C13 C12 C17 C16 -0.6(3) . . . . ?
C11 C12 C17 C16 -176.97(19) . . . . ?
C8 C7 O1 Ni1 16.8(3) . . . . ?
C6 C7 O1 Ni1 -165.37(13) . . . . ?
C10 C9 O2 Ni1 15.6(3) . . . 3_666 ?
C8 C9 O2 Ni1 -167.38(14) . . . 3_666 ?
C10 C9 O2 Ni1 173.70(14) . . . . ?
C8 C9 O2 Ni1 -9.3(3) . . . . ?
C10 C11 O3 Ni1 4.4(3) . . . 3_666 ?
C12 C11 O3 Ni1 -173.94(12) . . . 3_666 ?
C19 C18 O4 Ni1 -143.30(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656
C18 H18B O3 0.99 2.63 3.192(3) 116.2 3_666
O4 H4 O5 0.75(3) 2.10(3) 2.820(2) 160(3) 3_666
O5 H5A F6 0.79(3) 2.05(3) 2.693(2) 138(3) 1_545
O5 H5A O3 0.79(3) 2.27(3) 2.948(2) 145(3) 1_545
O5 H5B O1 0.86(3) 1.80(3) 2.614(2) 157(3) 3_656

_refine_diff_density_max         0.266
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_190403a1_a
_database_code_depnum_ccdc_archive 'CCDC 1914683'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H12 Cu2 F20 O8'
_chemical_formula_sum            'C36 H12 Cu2 F20 O8'
_chemical_formula_weight         1079.54

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.0933(7)
_cell_length_b                   13.6611(18)
_cell_length_c                   13.976(2)
_cell_angle_alpha                98.835(4)
_cell_angle_beta                 99.813(4)
_cell_angle_gamma                90.305(4)
_cell_volume                     946.3(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    150
_cell_measurement_reflns_used    120
_cell_measurement_theta_min      2.2947
_cell_measurement_theta_max      23.9657

_exptl_crystal_description       prismatic
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.894
_exptl_crystal_F_000             530
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.036
_exptl_absorpt_coefficient_mu    1.276
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.96

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            9003
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.995
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_full        25.027
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3311
_reflns_number_gt                2382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Instrument Service vV6.2.6'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C.B. Huebshle, rev 833)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0136P)²+6.7112P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3311
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.1475
_refine_ls_wR_factor_gt          0.1327
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.8743(15) 0.8485(5) 0.3524(5) 0.0299(17) Uani 1 1 d . . . . .
C2 C 1.0115(17) 0.9193(5) 0.3193(6) 0.0369(19) Uani 1 1 d . . . . .
C3 C 1.1365(16) 0.8944(6) 0.2394(6) 0.0358(19) Uani 1 1 d . . . . .
C4 C 1.1177(15) 0.7973(6) 0.1916(5) 0.0313(17) Uani 1 1 d . . . . .
C5 C 0.9752(14) 0.7279(5) 0.2259(5) 0.0266(16) Uani 1 1 d . . . . .
C6 C 0.8540(13) 0.7491(5) 0.3074(5) 0.0223(15) Uani 1 1 d . . . . .
C7 C 0.7248(13) 0.6709(5) 0.3520(5) 0.0231(15) Uani 1 1 d . . . . .
C8 C 0.5421(13) 0.6033(5) 0.2924(5) 0.0223(15) Uani 1 1 d . . . . .
H8 H 0.503145 0.609787 0.224734 0.027 Uiso 1 1 calc R U . . .
C9 C 0.4070(14) 0.5254(5) 0.3217(5) 0.0245(15) Uani 1 1 d . . . . .
C10 C 0.2330(13) 0.4567(5) 0.2526(5) 0.0215(15) Uani 1 1 d . . . . .
H10 H 0.226971 0.460443 0.184972 0.026 Uiso 1 1 calc R U . . .
C11 C 0.0721(13) 0.3851(5) 0.2751(5) 0.0235(15) Uani 1 1 d . . . . .
C12 C -0.1120(14) 0.3189(5) 0.1948(5) 0.0241(15) Uani 1 1 d . . . . .
C13 C -0.1173(16) 0.2170(6) 0.1946(5) 0.0334(18) Uani 1 1 d . . . . .
C14 C -0.3033(17) 0.1538(5) 0.1295(5) 0.0362(19) Uani 1 1 d . . . . .
C15 C -0.4923(16) 0.1939(6) 0.0641(6) 0.038(2) Uani 1 1 d . . . . .
C16 C -0.4851(16) 0.2929(6) 0.0615(5) 0.0377(19) Uani 1 1 d . . . . .
C17 C -0.2950(15) 0.3543(5) 0.1251(5) 0.0297(17) Uani 1 1 d . . . . .
C18 C 0.3917(16) 0.8018(5) 0.5771(6) 0.0381(19) Uani 1 1 d . . . . .
H18A H 0.569771 0.826300 0.572697 0.057 Uiso 1 1 calc R U . . .
H18B H 0.331534 0.839540 0.634443 0.057 Uiso 1 1 calc R U . . .
H18C H 0.267123 0.809958 0.517357 0.057 Uiso 1 1 calc R U . . .
Cu1 Cu 0.67601(18) 0.59387(6) 0.52541(6) 0.0231(2) Uani 1 1 d . . . . .
F1 F 0.7502(10) 0.8779(3) 0.4296(3) 0.0464(12) Uani 1 1 d . . . . .
F2 F 1.0291(12) 1.0136(3) 0.3661(4) 0.0594(15) Uani 1 1 d . . . . .
F3 F 1.2776(11) 0.9624(3) 0.2087(4) 0.0598(15) Uani 1 1 d . . . . .
F4 F 1.2408(10) 0.7723(3) 0.1156(3) 0.0491(13) Uani 1 1 d . . . . .
F5 F 0.9667(8) 0.6344(3) 0.1770(3) 0.0305(10) Uani 1 1 d . . . . .
F6 F 0.0616(10) 0.1764(3) 0.2564(3) 0.0461(12) Uani 1 1 d . . . . .
F7 F -0.3043(11) 0.0564(3) 0.1313(4) 0.0605(15) Uani 1 1 d . . . . .
F8 F -0.6758(11) 0.1336(4) 0.0010(4) 0.0659(16) Uani 1 1 d . . . . .
F9 F -0.6662(10) 0.3307(4) -0.0031(3) 0.0576(14) Uani 1 1 d . . . . .
F10 F -0.3005(8) 0.4515(3) 0.1184(3) 0.0350(10) Uani 1 1 d . . . . .
O1 O 0.8064(9) 0.6772(3) 0.4454(3) 0.0280(11) Uani 1 1 d . . . . .
O2 O 0.4445(9) 0.5152(4) 0.4159(3) 0.0283(11) Uani 1 1 d . . . . .
O3 O 0.0551(9) 0.3658(3) 0.3626(3) 0.0260(11) Uani 1 1 d . . . . .
O4 O 0.4013(12) 0.6999(4) 0.5869(4) 0.0403(14) Uani 1 1 d . . . . .
H4 H 0.24(2) 0.686(8) 0.597(8) 0.09(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.351(8) . ?
C1 C2 1.371(10) . ?
C1 C6 1.401(9) . ?
C2 F2 1.348(8) . ?
C2 C3 1.376(11) . ?
C3 F3 1.336(8) . ?
C3 C4 1.386(10) . ?
C4 F4 1.324(8) . ?
C4 C5 1.380(10) . ?
C5 F5 1.350(8) . ?
C5 C6 1.380(9) . ?
C6 C7 1.516(9) . ?
C7 O1 1.290(8) . ?
C7 C8 1.380(9) . ?
C8 C9 1.414(9) . ?
C8 H8 0.9500 . ?
C9 O2 1.327(8) . ?
C9 C10 1.421(9) . ?
C10 C11 1.378(9) . ?
C10 H10 0.9500 . ?
C11 O3 1.307(8) . ?
C11 C12 1.509(9) . ?
C12 C17 1.376(10) . ?
C12 C13 1.392(10) . ?
C13 F6 1.330(9) . ?
C13 C14 1.388(10) . ?
C14 F7 1.335(8) . ?
C14 C15 1.386(11) . ?
C15 F8 1.348(8) . ?
C15 C16 1.359(11) . ?
C16 F9 1.341(9) . ?
C16 C17 1.378(10) . ?
C17 F10 1.345(8) . ?
C18 O4 1.420(9) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
Cu1 O1 1.904(4) . ?
Cu1 O3 1.904(4) 2_666 ?
Cu1 O2 1.937(5) . ?
Cu1 O2 1.951(5) 2_666 ?
Cu1 O4 2.201(6) . ?
Cu1 Cu1 3.0420(17) 2_666 ?
O4 H4 0.88(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 117.7(6) . . ?
F1 C1 C6 120.0(6) . . ?
C2 C1 C6 122.3(6) . . ?
F2 C2 C1 120.0(7) . . ?
F2 C2 C3 119.6(6) . . ?
C1 C2 C3 120.4(7) . . ?
F3 C3 C2 120.7(7) . . ?
F3 C3 C4 120.0(7) . . ?
C2 C3 C4 119.3(6) . . ?
F4 C4 C5 121.3(7) . . ?
F4 C4 C3 119.7(6) . . ?
C5 C4 C3 118.9(7) . . ?
F5 C5 C6 120.1(6) . . ?
F5 C5 C4 116.2(6) . . ?
C6 C5 C4 123.6(7) . . ?
C5 C6 C1 115.4(6) . . ?
C5 C6 C7 123.6(6) . . ?
C1 C6 C7 120.8(6) . . ?
O1 C7 C8 127.7(6) . . ?
O1 C7 C6 112.8(6) . . ?
C8 C7 C6 119.4(6) . . ?
C7 C8 C9 126.6(6) . . ?
C7 C8 H8 116.7 . . ?
C9 C8 H8 116.7 . . ?
O2 C9 C8 119.5(6) . . ?
O2 C9 C10 118.9(6) . . ?
C8 C9 C10 121.7(6) . . ?
C11 C10 C9 125.8(6) . . ?
C11 C10 H10 117.1 . . ?
C9 C10 H10 117.1 . . ?
O3 C11 C10 126.9(6) . . ?
O3 C11 C12 112.4(6) . . ?
C10 C11 C12 120.7(6) . . ?
C17 C12 C13 116.9(6) . . ?
C17 C12 C11 123.4(6) . . ?
C13 C12 C11 119.5(6) . . ?
F6 C13 C14 117.5(7) . . ?
F6 C13 C12 120.5(6) . . ?
C14 C13 C12 122.0(7) . . ?
F7 C14 C15 120.6(7) . . ?
F7 C14 C13 120.7(7) . . ?
C15 C14 C13 118.8(7) . . ?
F8 C15 C16 120.6(7) . . ?
F8 C15 C14 119.5(7) . . ?
C16 C15 C14 119.9(7) . . ?
F9 C16 C15 119.3(7) . . ?
F9 C16 C17 120.1(7) . . ?
C15 C16 C17 120.5(7) . . ?
F10 C17 C12 121.0(6) . . ?
F10 C17 C16 117.2(6) . . ?
C12 C17 C16 121.8(7) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1 Cu1 O3 95.02(19) . 2_666 ?
O1 Cu1 O2 93.96(19) . . ?
O3 Cu1 O2 163.2(2) 2_666 . ?
O1 Cu1 O2 167.2(2) . 2_666 ?
O3 Cu1 O2 91.62(19) 2_666 2_666 ?
O2 Cu1 O2 77.0(2) . 2_666 ?
O1 Cu1 O4 96.9(2) . . ?
O3 Cu1 O4 90.4(2) 2_666 . ?
O2 Cu1 O4 102.6(2) . . ?
O2 Cu1 O4 94.0(2) 2_666 . ?
O1 Cu1 Cu1 132.00(14) . 2_666 ?
O3 Cu1 Cu1 128.88(14) 2_666 2_666 ?
O2 Cu1 Cu1 38.67(13) . 2_666 ?
O2 Cu1 Cu1 38.36(13) 2_666 2_666 ?
O4 Cu1 Cu1 100.60(15) . 2_666 ?
C7 O1 Cu1 123.9(4) . . ?
C9 O2 Cu1 128.2(4) . . ?
C9 O2 Cu1 128.2(4) . 2_666 ?
Cu1 O2 Cu1 103.0(2) . 2_666 ?
C11 O3 Cu1 122.9(4) . 2_666 ?
C18 O4 Cu1 125.1(5) . . ?
C18 O4 H4 103(7) . . ?
Cu1 O4 H4 126(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 2.9(12) . . . . ?
C6 C1 C2 F2 -178.8(7) . . . . ?
F1 C1 C2 C3 -178.4(7) . . . . ?
C6 C1 C2 C3 -0.2(13) . . . . ?
F2 C2 C3 F3 0.8(13) . . . . ?
C1 C2 C3 F3 -177.8(8) . . . . ?
F2 C2 C3 C4 180.0(7) . . . . ?
C1 C2 C3 C4 1.3(13) . . . . ?
F3 C3 C4 F4 0.2(12) . . . . ?
C2 C3 C4 F4 -178.9(7) . . . . ?
F3 C3 C4 C5 178.7(7) . . . . ?
C2 C3 C4 C5 -0.5(12) . . . . ?
F4 C4 C5 F5 -0.8(10) . . . . ?
C3 C4 C5 F5 -179.2(7) . . . . ?
F4 C4 C5 C6 176.8(7) . . . . ?
C3 C4 C5 C6 -1.6(11) . . . . ?
F5 C5 C6 C1 -179.8(6) . . . . ?
C4 C5 C6 C1 2.6(11) . . . . ?
F5 C5 C6 C7 4.8(10) . . . . ?
C4 C5 C6 C7 -172.8(7) . . . . ?
F1 C1 C6 C5 176.5(6) . . . . ?
C2 C1 C6 C5 -1.7(11) . . . . ?
F1 C1 C6 C7 -8.0(11) . . . . ?
C2 C1 C6 C7 173.8(7) . . . . ?
C5 C6 C7 O1 128.8(7) . . . . ?
C1 C6 C7 O1 -46.4(9) . . . . ?
C5 C6 C7 C8 -50.9(10) . . . . ?
C1 C6 C7 C8 133.9(7) . . . . ?
O1 C7 C8 C9 -0.7(12) . . . . ?
C6 C7 C8 C9 179.0(7) . . . . ?
C7 C8 C9 O2 2.9(11) . . . . ?
C7 C8 C9 C10 -176.6(7) . . . . ?
O2 C9 C10 C11 7.8(11) . . . . ?
C8 C9 C10 C11 -172.8(7) . . . . ?
C9 C10 C11 O3 -1.8(12) . . . . ?
C9 C10 C11 C12 177.7(6) . . . . ?
O3 C11 C12 C17 125.8(7) . . . . ?
C10 C11 C12 C17 -53.7(10) . . . . ?
O3 C11 C12 C13 -48.4(9) . . . . ?
C10 C11 C12 C13 132.1(7) . . . . ?
C17 C12 C13 F6 176.7(6) . . . . ?
C11 C12 C13 F6 -8.8(10) . . . . ?
C17 C12 C13 C14 -2.1(11) . . . . ?
C11 C12 C13 C14 172.5(7) . . . . ?
F6 C13 C14 F7 1.6(11) . . . . ?
C12 C13 C14 F7 -179.7(7) . . . . ?
F6 C13 C14 C15 -180.0(7) . . . . ?
C12 C13 C14 C15 -1.2(12) . . . . ?
F7 C14 C15 F8 -1.0(11) . . . . ?
C13 C14 C15 F8 -179.4(7) . . . . ?
F7 C14 C15 C16 -178.5(7) . . . . ?
C13 C14 C15 C16 3.1(12) . . . . ?
F8 C15 C16 F9 1.4(12) . . . . ?
C14 C15 C16 F9 178.9(7) . . . . ?
F8 C15 C16 C17 -179.1(7) . . . . ?
C14 C15 C16 C17 -1.6(12) . . . . ?
C13 C12 C17 F10 -178.5(6) . . . . ?
C11 C12 C17 F10 7.1(11) . . . . ?
C13 C12 C17 C16 3.6(11) . . . . ?
C11 C12 C17 C16 -170.7(7) . . . . ?
F9 C16 C17 F10 -0.3(11) . . . . ?
C15 C16 C17 F10 -179.8(7) . . . . ?
F9 C16 C17 C12 177.6(7) . . . . ?
C15 C16 C17 C12 -1.9(12) . . . . ?
C8 C7 O1 Cu1 -2.7(10) . . . . ?
C6 C7 O1 Cu1 177.6(4) . . . . ?
C8 C9 O2 Cu1 -1.6(10) . . . . ?
C10 C9 O2 Cu1 177.9(5) . . . . ?
C8 C9 O2 Cu1 -171.2(5) . . . 2_666 ?
C10 C9 O2 Cu1 8.3(9) . . . 2_666 ?
C10 C11 O3 Cu1 -19.4(10) . . . 2_666 ?
C12 C11 O3 Cu1 161.1(4) . . . 2_666 ?

_refine_diff_density_max         0.554
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.117

####################################################################### 
# 
# 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_130130a1_a
_database_code_depnum_ccdc_archive 'CCDC 1914682'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H16 Cu2 F20 O8'
_chemical_formula_sum            'C38 H16 Cu2 F20 O8'
_chemical_formula_weight         1107.59

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.605(2)
_cell_length_b                   13.738(3)
_cell_length_c                   13.967(3)
_cell_angle_alpha                98.221(2)
_cell_angle_beta                 94.599(2)
_cell_angle_gamma                99.350(2)
_cell_volume                     1976.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173
_cell_measurement_reflns_used    8669
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.87

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_F_000             1092
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.224
_shelx_estimated_absorpt_T_min   0.749
_shelx_estimated_absorpt_T_max   0.828
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.83

_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            21245
_diffrn_reflns_av_unetI/netI     0.0237
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.258
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             8008
_reflns_number_gt                6632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0463P)²+1.4424P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8008
_refine_ls_number_parameters     623
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0967
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5425(3) 0.65355(19) 0.15889(18) 0.0338(6) Uani 1 1 d . . . . .
C2 C 0.4722(3) 0.6933(2) 0.09184(18) 0.0414(7) Uani 1 1 d . . . . .
C3 C 0.4239(3) 0.7781(2) 0.1212(2) 0.0417(7) Uani 1 1 d . . . . .
C4 C 0.4459(2) 0.82243(18) 0.2164(2) 0.0343(6) Uani 1 1 d . . . . .
C5 C 0.5166(2) 0.78192(17) 0.28292(16) 0.0250(5) Uani 1 1 d . . . . .
C6 C 0.5666(2) 0.69615(17) 0.25649(16) 0.0240(5) Uani 1 1 d . . . . .
C7 C 0.6338(2) 0.64623(16) 0.33022(16) 0.0234(5) Uani 1 1 d . . . . .
C8 C 0.7321(2) 0.70418(17) 0.39521(16) 0.0247(5) Uani 1 1 d . . . . .
H8 H 0.756980 0.771804 0.386886 0.030 Uiso 1 1 calc R U . . .
C9 C 0.7985(2) 0.67148(16) 0.47273(16) 0.0229(5) Uani 1 1 d . . . . .
C10 C 0.8902(2) 0.73941(16) 0.54029(16) 0.0242(5) Uani 1 1 d . . . . .
H10 H 0.898767 0.808155 0.534420 0.029 Uiso 1 1 calc R U . . .
C11 C 0.9682(2) 0.71473(16) 0.61377(16) 0.0231(5) Uani 1 1 d . . . . .
C12 C 1.0623(2) 0.79633(16) 0.67756(16) 0.0227(5) Uani 1 1 d . . . . .
C13 C 1.0701(3) 0.80389(19) 0.77861(18) 0.0334(6) Uani 1 1 d . . . . .
C14 C 1.1620(3) 0.8722(2) 0.83927(18) 0.0398(6) Uani 1 1 d . . . . .
C15 C 1.2506(3) 0.93552(18) 0.8006(2) 0.0385(6) Uani 1 1 d . . . . .
C16 C 1.2443(2) 0.93213(18) 0.7018(2) 0.0360(6) Uani 1 1 d . . . . .
C17 C 1.1499(2) 0.86428(17) 0.64165(17) 0.0262(5) Uani 1 1 d . . . . .
C18 C 0.9079(2) 0.32429(18) 0.84444(17) 0.0301(5) Uani 1 1 d . . . . .
C19 C 0.9749(3) 0.2891(2) 0.91706(18) 0.0403(7) Uani 1 1 d . . . . .
C20 C 1.0475(3) 0.2172(2) 0.89318(19) 0.0423(7) Uani 1 1 d . . . . .
C21 C 1.0527(3) 0.18059(18) 0.79707(19) 0.0348(6) Uani 1 1 d . . . . .
C22 C 0.9840(2) 0.21602(16) 0.72526(16) 0.0243(5) Uani 1 1 d . . . . .
C23 C 0.9117(2) 0.28974(16) 0.74650(15) 0.0220(5) Uani 1 1 d . . . . .
C24 C 0.8497(2) 0.33766(16) 0.66844(16) 0.0218(4) Uani 1 1 d . . . . .
C25 C 0.7550(2) 0.27889(16) 0.60139(16) 0.0236(5) Uani 1 1 d . . . . .
H25 H 0.730048 0.211148 0.609315 0.028 Uiso 1 1 calc R U . . .
C26 C 0.6920(2) 0.31153(16) 0.52189(16) 0.0218(4) Uani 1 1 d . . . . .
C27 C 0.6027(2) 0.24279(16) 0.45245(16) 0.0241(5) Uani 1 1 d . . . . .
H27 H 0.594264 0.173930 0.457811 0.029 Uiso 1 1 calc R U . . .
C28 C 0.5279(2) 0.26834(16) 0.37835(16) 0.0225(5) Uani 1 1 d . . . . .
C29 C 0.4322(2) 0.18789(16) 0.31318(16) 0.0241(5) Uani 1 1 d . . . . .
C30 C 0.4330(3) 0.17615(19) 0.21269(18) 0.0347(6) Uani 1 1 d . . . . .
C31 C 0.3376(3) 0.1128(2) 0.15008(19) 0.0407(6) Uani 1 1 d . . . . .
C32 C 0.2376(3) 0.05900(19) 0.1872(2) 0.0392(6) Uani 1 1 d . . . . .
C33 C 0.2353(2) 0.06639(18) 0.2859(2) 0.0346(6) Uani 1 1 d . . . . .
C34 C 0.3335(2) 0.12896(17) 0.34782(17) 0.0275(5) Uani 1 1 d . . . . .
C35 C 0.7620(2) 0.40724(19) 0.19780(18) 0.0321(5) Uani 1 1 d . . . . .
H35A H 0.670864 0.412747 0.182768 0.039 Uiso 1 1 calc R U . . .
H35B H 0.774080 0.340658 0.166134 0.039 Uiso 1 1 calc R U . . .
C36 C 0.8449(3) 0.4856(2) 0.1568(2) 0.0444(7) Uani 1 1 d . . . . .
H36A H 0.835253 0.551728 0.189174 0.067 Uiso 1 1 calc R U . . .
H36B H 0.819224 0.479237 0.086881 0.067 Uiso 1 1 calc R U . . .
H36C H 0.934841 0.477508 0.167280 0.067 Uiso 1 1 calc R U . . .
C37 C 0.7192(4) 0.5620(4) 0.7899(3) 0.0826(13) Uani 1 1 d . . . . .
H37A H 0.673247 0.492678 0.787061 0.099 Uiso 1 1 calc R U . . .
H37B H 0.811278 0.560856 0.807154 0.099 Uiso 1 1 calc R U . . .
C38 C 0.6814(6) 0.6157(4) 0.8653(3) 0.1159(19) Uani 1 1 d . . . . .
H38A H 0.720642 0.686000 0.869214 0.174 Uiso 1 1 calc R U . . .
H38B H 0.707913 0.591583 0.925153 0.174 Uiso 1 1 calc R U . . .
H38C H 0.587569 0.609164 0.857127 0.174 Uiso 1 1 calc R U . . .
Cu1 Cu 0.65726(2) 0.46802(2) 0.40330(2) 0.02269(9) Uani 1 1 d . . . . .
Cu2 Cu 0.83523(3) 0.51579(2) 0.59185(2) 0.02413(9) Uani 1 1 d . . . . .
F1 F 0.58854(18) 0.57108(13) 0.12644(11) 0.0552(5) Uani 1 1 d . . . . .
F2 F 0.4497(2) 0.64877(16) -0.00080(12) 0.0695(6) Uani 1 1 d . . . . .
F3 F 0.3543(2) 0.81685(16) 0.05697(14) 0.0685(6) Uani 1 1 d . . . . .
F4 F 0.39603(18) 0.90408(12) 0.24605(13) 0.0554(5) Uani 1 1 d . . . . .
F5 F 0.53214(14) 0.82721(10) 0.37528(10) 0.0336(3) Uani 1 1 d . . . . .
F6 F 0.98498(18) 0.74449(14) 0.81873(11) 0.0596(5) Uani 1 1 d . . . . .
F7 F 1.1644(2) 0.87755(15) 0.93581(12) 0.0668(6) Uani 1 1 d . . . . .
F8 F 1.34183(18) 1.00127(13) 0.85836(13) 0.0611(5) Uani 1 1 d . . . . .
F9 F 1.32877(18) 0.99453(13) 0.66348(14) 0.0623(5) Uani 1 1 d . . . . .
F10 F 1.14788(15) 0.86584(11) 0.54615(10) 0.0399(4) Uani 1 1 d . . . . .
F11 F 0.83839(17) 0.39464(12) 0.87127(11) 0.0454(4) Uani 1 1 d . . . . .
F12 F 0.9686(2) 0.32573(15) 1.01021(11) 0.0709(6) Uani 1 1 d . . . . .
F13 F 1.1126(2) 0.18234(14) 0.96283(13) 0.0691(6) Uani 1 1 d . . . . .
F14 F 1.12406(17) 0.11068(13) 0.77282(13) 0.0549(5) Uani 1 1 d . . . . .
F15 F 0.99148(14) 0.17752(10) 0.63285(10) 0.0343(3) Uani 1 1 d . . . . .
F16 F 0.52951(17) 0.22644(14) 0.17393(11) 0.0534(5) Uani 1 1 d . . . . .
F17 F 0.3419(2) 0.10425(16) 0.05393(12) 0.0691(6) Uani 1 1 d . . . . .
F18 F 0.14277(18) -0.00202(13) 0.12782(13) 0.0625(5) Uani 1 1 d . . . . .
F19 F 0.13927(17) 0.01245(13) 0.32257(13) 0.0572(5) Uani 1 1 d . . . . .
F20 F 0.32776(14) 0.13202(11) 0.44337(10) 0.0390(4) Uani 1 1 d . . . . .
H7A H 0.854(3) 0.403(2) 0.312(2) 0.029(8) Uiso 1 1 d . . . . .
H8A H 0.641(3) 0.599(3) 0.684(2) 0.057(10) Uiso 1 1 d . . . . .
O1 O 0.58892(16) 0.55288(11) 0.32405(11) 0.0282(4) Uani 1 1 d . . . . .
O2 O 0.77503(15) 0.57704(11) 0.48358(11) 0.0281(4) Uani 1 1 d . . . . .
O3 O 0.97138(15) 0.62685(11) 0.63630(11) 0.0263(4) Uani 1 1 d . . . . .
O4 O 0.89555(16) 0.43078(11) 0.67459(12) 0.0285(4) Uani 1 1 d . . . . .
O5 O 0.71624(15) 0.40588(11) 0.51165(11) 0.0255(3) Uani 1 1 d . . . . .
O6 O 0.52527(14) 0.35579(11) 0.35498(11) 0.0248(3) Uani 1 1 d . . . . .
O7 O 0.78995(18) 0.41492(16) 0.30114(13) 0.0401(5) Uani 1 1 d . . . . .
O8 O 0.70873(19) 0.58200(17) 0.69587(14) 0.0458(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 F1 1.340(3) . ?
C1 C2 1.377(3) . ?
C1 C6 1.391(3) . ?
C2 F2 1.335(3) . ?
C2 C3 1.370(4) . ?
C3 F3 1.338(3) . ?
C3 C4 1.367(4) . ?
C4 F4 1.344(3) . ?
C4 C5 1.380(3) . ?
C5 F5 1.335(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.510(3) . ?
C7 O1 1.281(3) . ?
C7 C8 1.384(3) . ?
C8 C9 1.410(3) . ?
C8 H8 0.9500 . ?
C9 O2 1.314(3) . ?
C9 C10 1.419(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.9500 . ?
C11 O3 1.295(3) . ?
C11 C12 1.502(3) . ?
C12 C17 1.383(3) . ?
C12 C13 1.395(3) . ?
C13 F6 1.330(3) . ?
C13 C14 1.375(4) . ?
C14 F7 1.338(3) . ?
C14 C15 1.372(4) . ?
C15 F8 1.336(3) . ?
C15 C16 1.369(4) . ?
C16 F9 1.335(3) . ?
C16 C17 1.384(3) . ?
C17 F10 1.336(3) . ?
C18 F11 1.338(3) . ?
C18 C19 1.380(3) . ?
C18 C23 1.388(3) . ?
C19 F12 1.337(3) . ?
C19 C20 1.369(4) . ?
C20 F13 1.336(3) . ?
C20 C21 1.373(4) . ?
C21 F14 1.339(3) . ?
C21 C22 1.383(3) . ?
C22 F15 1.337(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.511(3) . ?
C24 O4 1.281(3) . ?
C24 C25 1.381(3) . ?
C25 C26 1.414(3) . ?
C25 H25 0.9500 . ?
C26 O5 1.310(3) . ?
C26 C27 1.425(3) . ?
C27 C28 1.374(3) . ?
C27 H27 0.9500 . ?
C28 O6 1.293(3) . ?
C28 C29 1.509(3) . ?
C29 C34 1.379(3) . ?
C29 C30 1.390(3) . ?
C30 F16 1.335(3) . ?
C30 C31 1.379(3) . ?
C31 F17 1.336(3) . ?
C31 C32 1.372(4) . ?
C32 F18 1.340(3) . ?
C32 C33 1.370(4) . ?
C33 F19 1.340(3) . ?
C33 C34 1.387(3) . ?
C34 F20 1.336(3) . ?
C35 O7 1.435(3) . ?
C35 C36 1.486(4) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.325(5) . ?
C37 O8 1.380(4) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 H38A 0.9800 . ?
C38 H38B 0.9800 . ?
C38 H38C 0.9800 . ?
Cu1 O1 1.9038(15) . ?
Cu1 O6 1.9083(15) . ?
Cu1 O2 1.9359(15) . ?
Cu1 O5 1.9498(15) . ?
Cu1 O7 2.215(2) . ?
Cu1 Cu2 3.0387(6) . ?
Cu2 O4 1.9024(15) . ?
Cu2 O3 1.9152(15) . ?
Cu2 O2 1.9458(15) . ?
Cu2 O5 1.9486(15) . ?
Cu2 O8 2.251(2) . ?
O7 H7A 0.73(3) . ?
O8 H8A 0.81(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C2 117.3(2) . . ?
F1 C1 C6 120.3(2) . . ?
C2 C1 C6 122.4(2) . . ?
F2 C2 C3 120.2(2) . . ?
F2 C2 C1 120.2(3) . . ?
C3 C2 C1 119.5(2) . . ?
F3 C3 C4 120.1(3) . . ?
F3 C3 C2 120.1(3) . . ?
C4 C3 C2 119.8(2) . . ?
F4 C4 C3 120.0(2) . . ?
F4 C4 C5 119.8(2) . . ?
C3 C4 C5 120.1(2) . . ?
F5 C5 C4 117.3(2) . . ?
F5 C5 C6 120.73(19) . . ?
C4 C5 C6 122.0(2) . . ?
C5 C6 C1 116.1(2) . . ?
C5 C6 C7 122.3(2) . . ?
C1 C6 C7 121.4(2) . . ?
O1 C7 C8 128.3(2) . . ?
O1 C7 C6 113.51(19) . . ?
C8 C7 C6 118.23(19) . . ?
C7 C8 C9 125.6(2) . . ?
C7 C8 H8 117.2 . . ?
C9 C8 H8 117.2 . . ?
O2 C9 C8 119.97(19) . . ?
O2 C9 C10 119.06(19) . . ?
C8 C9 C10 121.0(2) . . ?
C11 C10 C9 126.0(2) . . ?
C11 C10 H10 117.0 . . ?
C9 C10 H10 117.0 . . ?
O3 C11 C10 127.7(2) . . ?
O3 C11 C12 113.42(18) . . ?
C10 C11 C12 118.89(19) . . ?
C17 C12 C13 116.0(2) . . ?
C17 C12 C11 123.4(2) . . ?
C13 C12 C11 120.6(2) . . ?
F6 C13 C14 118.2(2) . . ?
F6 C13 C12 119.5(2) . . ?
C14 C13 C12 122.4(2) . . ?
F7 C14 C15 120.0(2) . . ?
F7 C14 C13 120.2(3) . . ?
C15 C14 C13 119.8(2) . . ?
F8 C15 C16 119.7(3) . . ?
F8 C15 C14 120.7(2) . . ?
C16 C15 C14 119.6(2) . . ?
F9 C16 C15 120.1(2) . . ?
F9 C16 C17 119.9(2) . . ?
C15 C16 C17 120.0(2) . . ?
F10 C17 C12 120.8(2) . . ?
F10 C17 C16 117.0(2) . . ?
C12 C17 C16 122.1(2) . . ?
F11 C18 C19 117.6(2) . . ?
F11 C18 C23 120.1(2) . . ?
C19 C18 C23 122.3(2) . . ?
F12 C19 C20 120.6(2) . . ?
F12 C19 C18 119.7(2) . . ?
C20 C19 C18 119.8(2) . . ?
F13 C20 C19 120.3(3) . . ?
F13 C20 C21 120.0(3) . . ?
C19 C20 C21 119.7(2) . . ?
F14 C21 C20 120.2(2) . . ?
F14 C21 C22 120.0(2) . . ?
C20 C21 C22 119.8(2) . . ?
F15 C22 C23 120.28(19) . . ?
F15 C22 C21 117.6(2) . . ?
C23 C22 C21 122.1(2) . . ?
C22 C23 C18 116.3(2) . . ?
C22 C23 C24 122.3(2) . . ?
C18 C23 C24 121.1(2) . . ?
O4 C24 C25 128.6(2) . . ?
O4 C24 C23 112.87(18) . . ?
C25 C24 C23 118.49(19) . . ?
C24 C25 C26 125.2(2) . . ?
C24 C25 H25 117.4 . . ?
C26 C25 H25 117.4 . . ?
O5 C26 C25 119.79(19) . . ?
O5 C26 C27 119.52(19) . . ?
C25 C26 C27 120.7(2) . . ?
C28 C27 C26 125.1(2) . . ?
C28 C27 H27 117.5 . . ?
C26 C27 H27 117.5 . . ?
O6 C28 C27 128.6(2) . . ?
O6 C28 C29 112.08(18) . . ?
C27 C28 C29 119.29(19) . . ?
C34 C29 C30 116.4(2) . . ?
C34 C29 C28 122.8(2) . . ?
C30 C29 C28 120.5(2) . . ?
F16 C30 C31 117.8(2) . . ?
F16 C30 C29 119.9(2) . . ?
C31 C30 C29 122.3(2) . . ?
F17 C31 C32 120.2(2) . . ?
F17 C31 C30 120.3(3) . . ?
C32 C31 C30 119.5(2) . . ?
F18 C32 C33 119.5(3) . . ?
F18 C32 C31 120.6(3) . . ?
C33 C32 C31 119.9(2) . . ?
F19 C33 C32 120.1(2) . . ?
F19 C33 C34 120.0(2) . . ?
C32 C33 C34 119.8(2) . . ?
F20 C34 C29 120.7(2) . . ?
F20 C34 C33 117.4(2) . . ?
C29 C34 C33 121.9(2) . . ?
O7 C35 C36 112.6(2) . . ?
O7 C35 H35A 109.1 . . ?
C36 C35 H35A 109.1 . . ?
O7 C35 H35B 109.1 . . ?
C36 C35 H35B 109.1 . . ?
H35A C35 H35B 107.8 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 O8 124.6(4) . . ?
C38 C37 H37A 106.2 . . ?
O8 C37 H37A 106.2 . . ?
C38 C37 H37B 106.2 . . ?
O8 C37 H37B 106.2 . . ?
H37A C37 H37B 106.4 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O1 Cu1 O6 93.91(7) . . ?
O1 Cu1 O2 93.64(7) . . ?
O6 Cu1 O2 165.43(7) . . ?
O1 Cu1 O5 165.07(7) . . ?
O6 Cu1 O5 92.51(6) . . ?
O2 Cu1 O5 77.37(6) . . ?
O1 Cu1 O7 96.52(7) . . ?
O6 Cu1 O7 92.23(7) . . ?
O2 Cu1 O7 99.27(8) . . ?
O5 Cu1 O7 96.68(7) . . ?
O1 Cu1 Cu2 131.22(5) . . ?
O6 Cu1 Cu2 130.51(5) . . ?
O2 Cu1 Cu2 38.59(4) . . ?
O5 Cu1 Cu2 38.77(4) . . ?
O7 Cu1 Cu2 100.09(5) . . ?
O4 Cu2 O3 95.34(7) . . ?
O4 Cu2 O2 166.70(7) . . ?
O3 Cu2 O2 92.36(6) . . ?
O4 Cu2 O5 92.84(7) . . ?
O3 Cu2 O5 163.77(7) . . ?
O2 Cu2 O5 77.16(6) . . ?
O4 Cu2 O8 96.01(8) . . ?
O3 Cu2 O8 90.36(8) . . ?
O2 Cu2 O8 94.76(7) . . ?
O5 Cu2 O8 102.71(8) . . ?
O4 Cu2 Cu1 131.04(5) . . ?
O3 Cu2 Cu1 129.58(5) . . ?
O2 Cu2 Cu1 38.36(5) . . ?
O5 Cu2 Cu1 38.80(4) . . ?
O8 Cu2 Cu1 101.29(5) . . ?
C7 O1 Cu1 123.65(14) . . ?
C9 O2 Cu1 128.34(14) . . ?
C9 O2 Cu2 128.29(14) . . ?
Cu1 O2 Cu2 103.04(7) . . ?
C11 O3 Cu2 122.20(14) . . ?
C24 O4 Cu2 124.25(14) . . ?
C26 O5 Cu2 129.00(13) . . ?
C26 O5 Cu1 128.21(14) . . ?
Cu2 O5 Cu1 102.42(7) . . ?
C28 O6 Cu1 122.38(14) . . ?
C35 O7 Cu1 121.60(15) . . ?
C35 O7 H7A 110(2) . . ?
Cu1 O7 H7A 129(2) . . ?
C37 O8 Cu2 117.8(2) . . ?
C37 O8 H8A 110(2) . . ?
Cu2 O8 H8A 128(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 1.5(4) . . . . ?
C6 C1 C2 F2 -178.9(3) . . . . ?
F1 C1 C2 C3 -179.5(3) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
F2 C2 C3 F3 -0.3(5) . . . . ?
C1 C2 C3 F3 -179.3(3) . . . . ?
F2 C2 C3 C4 179.1(3) . . . . ?
C1 C2 C3 C4 0.1(5) . . . . ?
F3 C3 C4 F4 1.1(4) . . . . ?
C2 C3 C4 F4 -178.3(3) . . . . ?
F3 C3 C4 C5 179.4(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
F4 C4 C5 F5 -0.1(3) . . . . ?
C3 C4 C5 F5 -178.4(2) . . . . ?
F4 C4 C5 C6 178.0(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
F5 C5 C6 C1 178.5(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
F5 C5 C6 C7 3.6(3) . . . . ?
C4 C5 C6 C7 -174.4(2) . . . . ?
F1 C1 C6 C5 179.2(2) . . . . ?
C2 C1 C6 C5 -0.4(4) . . . . ?
F1 C1 C6 C7 -5.9(4) . . . . ?
C2 C1 C6 C7 174.5(2) . . . . ?
C5 C6 C7 O1 127.6(2) . . . . ?
C1 C6 C7 O1 -47.0(3) . . . . ?
C5 C6 C7 C8 -51.7(3) . . . . ?
C1 C6 C7 C8 133.7(3) . . . . ?
O1 C7 C8 C9 -3.9(4) . . . . ?
C6 C7 C8 C9 175.3(2) . . . . ?
C7 C8 C9 O2 5.0(4) . . . . ?
C7 C8 C9 C10 -174.4(2) . . . . ?
O2 C9 C10 C11 6.2(4) . . . . ?
C8 C9 C10 C11 -174.4(2) . . . . ?
C9 C10 C11 O3 -1.3(4) . . . . ?
C9 C10 C11 C12 178.7(2) . . . . ?
O3 C11 C12 C17 127.5(2) . . . . ?
C10 C11 C12 C17 -52.5(3) . . . . ?
O3 C11 C12 C13 -49.0(3) . . . . ?
C10 C11 C12 C13 131.0(2) . . . . ?
C17 C12 C13 F6 176.6(2) . . . . ?
C11 C12 C13 F6 -6.7(4) . . . . ?
C17 C12 C13 C14 -2.2(4) . . . . ?
C11 C12 C13 C14 174.5(2) . . . . ?
F6 C13 C14 F7 0.2(4) . . . . ?
C12 C13 C14 F7 179.1(2) . . . . ?
F6 C13 C14 C15 -179.3(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
F7 C14 C15 F8 1.6(4) . . . . ?
C13 C14 C15 F8 -178.9(2) . . . . ?
F7 C14 C15 C16 -177.5(3) . . . . ?
C13 C14 C15 C16 2.0(4) . . . . ?
F8 C15 C16 F9 -0.2(4) . . . . ?
C14 C15 C16 F9 178.9(3) . . . . ?
F8 C15 C16 C17 -179.9(2) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C13 C12 C17 F10 -177.6(2) . . . . ?
C11 C12 C17 F10 5.7(3) . . . . ?
C13 C12 C17 C16 3.5(3) . . . . ?
C11 C12 C17 C16 -173.2(2) . . . . ?
F9 C16 C17 F10 -0.7(4) . . . . ?
C15 C16 C17 F10 179.0(2) . . . . ?
F9 C16 C17 C12 178.3(2) . . . . ?
C15 C16 C17 C12 -2.1(4) . . . . ?
F11 C18 C19 F12 -0.1(4) . . . . ?
C23 C18 C19 F12 179.4(2) . . . . ?
F11 C18 C19 C20 -179.9(3) . . . . ?
C23 C18 C19 C20 -0.4(4) . . . . ?
F12 C19 C20 F13 0.4(5) . . . . ?
C18 C19 C20 F13 -179.8(3) . . . . ?
F12 C19 C20 C21 180.0(3) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
F13 C20 C21 F14 -0.8(4) . . . . ?
C19 C20 C21 F14 179.6(3) . . . . ?
F13 C20 C21 C22 179.2(3) . . . . ?
C19 C20 C21 C22 -0.5(4) . . . . ?
F14 C21 C22 F15 0.4(4) . . . . ?
C20 C21 C22 F15 -179.6(2) . . . . ?
F14 C21 C22 C23 -178.4(2) . . . . ?
C20 C21 C22 C23 1.7(4) . . . . ?
F15 C22 C23 C18 179.1(2) . . . . ?
C21 C22 C23 C18 -2.2(3) . . . . ?
F15 C22 C23 C24 -6.4(3) . . . . ?
C21 C22 C23 C24 172.3(2) . . . . ?
F11 C18 C23 C22 -179.0(2) . . . . ?
C19 C18 C23 C22 1.5(4) . . . . ?
F11 C18 C23 C24 6.5(3) . . . . ?
C19 C18 C23 C24 -173.0(2) . . . . ?
C22 C23 C24 O4 -115.3(2) . . . . ?
C18 C23 C24 O4 58.9(3) . . . . ?
C22 C23 C24 C25 64.5(3) . . . . ?
C18 C23 C24 C25 -121.3(2) . . . . ?
O4 C24 C25 C26 2.6(4) . . . . ?
C23 C24 C25 C26 -177.1(2) . . . . ?
C24 C25 C26 O5 -4.8(4) . . . . ?
C24 C25 C26 C27 175.0(2) . . . . ?
O5 C26 C27 C28 -6.7(4) . . . . ?
C25 C26 C27 C28 173.5(2) . . . . ?
C26 C27 C28 O6 2.2(4) . . . . ?
C26 C27 C28 C29 -176.9(2) . . . . ?
O6 C28 C29 C34 -119.5(2) . . . . ?
C27 C28 C29 C34 59.7(3) . . . . ?
O6 C28 C29 C30 54.4(3) . . . . ?
C27 C28 C29 C30 -126.4(3) . . . . ?
C34 C29 C30 F16 -176.2(2) . . . . ?
C28 C29 C30 F16 9.5(4) . . . . ?
C34 C29 C30 C31 3.0(4) . . . . ?
C28 C29 C30 C31 -171.4(2) . . . . ?
F16 C30 C31 F17 -1.2(4) . . . . ?
C29 C30 C31 F17 179.6(3) . . . . ?
F16 C30 C31 C32 179.3(3) . . . . ?
C29 C30 C31 C32 0.1(4) . . . . ?
F17 C31 C32 F18 -0.5(4) . . . . ?
C30 C31 C32 F18 179.0(3) . . . . ?
F17 C31 C32 C33 178.5(3) . . . . ?
C30 C31 C32 C33 -2.0(4) . . . . ?
F18 C32 C33 F19 0.4(4) . . . . ?
C31 C32 C33 F19 -178.6(3) . . . . ?
F18 C32 C33 C34 179.6(2) . . . . ?
C31 C32 C33 C34 0.6(4) . . . . ?
C30 C29 C34 F20 177.2(2) . . . . ?
C28 C29 C34 F20 -8.6(3) . . . . ?
C30 C29 C34 C33 -4.3(3) . . . . ?
C28 C29 C34 C33 169.8(2) . . . . ?
F19 C33 C34 F20 0.4(3) . . . . ?
C32 C33 C34 F20 -178.8(2) . . . . ?
F19 C33 C34 C29 -178.1(2) . . . . ?
C32 C33 C34 C29 2.7(4) . . . . ?
C8 C7 O1 Cu1 -3.3(3) . . . . ?
C6 C7 O1 Cu1 177.47(14) . . . . ?
C8 C9 O2 Cu1 1.0(3) . . . . ?
C10 C9 O2 Cu1 -179.52(16) . . . . ?
C8 C9 O2 Cu2 -171.32(16) . . . . ?
C10 C9 O2 Cu2 8.2(3) . . . . ?
C10 C11 O3 Cu2 -16.7(3) . . . . ?
C12 C11 O3 Cu2 163.29(14) . . . . ?
C25 C24 O4 Cu2 3.1(3) . . . . ?
C23 C24 O4 Cu2 -177.21(14) . . . . ?
C25 C26 O5 Cu2 1.4(3) . . . . ?
C27 C26 O5 Cu2 -178.36(15) . . . . ?
C25 C26 O5 Cu1 173.26(15) . . . . ?
C27 C26 O5 Cu1 -6.6(3) . . . . ?
C27 C28 O6 Cu1 14.8(3) . . . . ?
C29 C28 O6 Cu1 -166.10(14) . . . . ?
C36 C35 O7 Cu1 107.7(2) . . . . ?
C38 C37 O8 Cu2 159.9(5) . . . . ?

_refine_diff_density_max         1.112
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.065

####################################################################### 
# 
# 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_fdx11_p21c
_database_code_depnum_ccdc_archive 'CCDC 1914681'
loop_
_audit_author_name
_audit_author_address
'Akiko Hori'
;Shibaura Institute of Technology
Japan
;
_audit_update_record             
;
2019-05-08 deposited with the CCDC.	2024-05-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C38 H20 F20 Ni2 O10, 4(C H4 O)'
_chemical_formula_sum            'C42 H36 F20 Ni2 O14'
_chemical_formula_weight         1262.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.4777(5)
_cell_length_b                   13.9837(4)
_cell_length_c                   14.3744(5)
_cell_angle_alpha                90
_cell_angle_beta                 102.5520(10)
_cell_angle_gamma                90
_cell_volume                     2448.16(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    93
_cell_measurement_reflns_used    5269
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      25.04

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.712
_exptl_crystal_F_000             1272
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.122
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.085
_exptl_absorpt_coefficient_mu    0.909
_shelx_estimated_absorpt_T_min   0.897
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.861
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_process_details   
;
SADABS Sheldrick 1996
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      93
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro focus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            16725
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0530
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.217
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4309
_reflns_number_gt                3444
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'Bruker Instrument Service V4.2.7 (Bruker AXS Inc., 2015)'
_computing_cell_refinement       'APEX2 v2015.5 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XSHELL V6.3.1 (Bruker AXS Inc., 2004)'
_computing_publication_material  
'Generate Report V2014.1 (Bruker AXS Inc., 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+2.1041P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4309
_refine_ls_number_parameters     372
_refine_ls_number_restraints     450
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0772
_refine_ls_wR_factor_gt          0.0708
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.003
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1146(2) 0.25776(19) 0.55020(19) 0.0200(6) Uani 1 1 d . U . . .
C2 C 0.0381(2) 0.1854(2) 0.5449(2) 0.0267(7) Uani 1 1 d . U . . .
C3 C -0.0043(2) 0.14349(19) 0.4581(2) 0.0271(7) Uani 1 1 d . U . . .
C4 C 0.0279(2) 0.1743(2) 0.3781(2) 0.0266(7) Uani 1 1 d . U . . .
C5 C 0.1037(2) 0.2470(2) 0.3856(2) 0.0237(6) Uani 1 1 d . U . . .
C6 C 0.1502(2) 0.29006(18) 0.47147(18) 0.0147(6) Uani 1 1 d . U . . .
C7 C 0.2420(2) 0.36225(19) 0.48057(18) 0.0154(6) Uani 1 1 d . U . . .
C8 C 0.2174(2) 0.45096(18) 0.43852(19) 0.0171(6) Uani 1 1 d . U . . .
H8 H 0.142575 0.463011 0.410041 0.020 Uiso 1 1 calc R U . . .
C9 C 0.2930(2) 0.52553(18) 0.43377(18) 0.0147(6) Uani 1 1 d . U . . .
C10 C 0.2541(2) 0.61320(18) 0.38703(18) 0.0171(6) Uani 1 1 d . U . . .
H10 H 0.177481 0.617592 0.360917 0.021 Uiso 1 1 calc R U . . .
C11 C 0.3165(2) 0.69160(18) 0.37617(19) 0.0162(6) Uani 1 1 d . U . . .
C12 C 0.2573(2) 0.77634(18) 0.32345(19) 0.0172(6) Uani 1 1 d . U . . .
C13 C 0.2158(2) 0.77558(18) 0.22599(19) 0.0172(6) Uani 1 1 d . U . . .
C14 C 0.1652(2) 0.8538(2) 0.1772(2) 0.0211(6) Uani 1 1 d . U . . .
C15 C 0.1544(2) 0.93623(19) 0.2267(2) 0.0256(7) Uani 1 1 d . U . . .
C16 C 0.1957(2) 0.9403(2) 0.3231(2) 0.0283(7) Uani 1 1 d . U . . .
C17 C 0.2464(2) 0.8612(2) 0.3703(2) 0.0245(7) Uani 1 1 d . U . . .
C18 C 0.5767(2) 0.3149(2) 0.3720(2) 0.0296(7) Uani 1 1 d . U . . .
H18A H 0.560458 0.287568 0.307657 0.044 Uiso 1 1 calc R U . . .
H18C H 0.618417 0.268563 0.416782 0.044 Uiso 1 1 calc R U . . .
H18B H 0.619994 0.373422 0.372502 0.044 Uiso 1 1 calc R U . . .
C19 C 0.4110(3) 0.4056(3) 0.7309(2) 0.0503(10) Uani 1 1 d . U . . .
H19A H 0.334214 0.394962 0.698725 0.075 Uiso 1 1 calc R U . . .
H19B H 0.413876 0.447152 0.786287 0.075 Uiso 1 1 calc R U . . .
H19C H 0.445592 0.344099 0.751995 0.075 Uiso 1 1 calc R U . . .
C20 C 0.7316(2) 0.5519(2) 0.8116(2) 0.0365(8) Uani 1 1 d . U . . .
H20A H 0.769919 0.526588 0.764084 0.055 Uiso 1 1 calc R U . . .
H20B H 0.735631 0.505199 0.863057 0.055 Uiso 1 1 calc R U . . .
H20C H 0.766442 0.611750 0.837742 0.055 Uiso 1 1 calc R U . . .
C21 C 0.5767(3) 0.6072(2) 0.9978(2) 0.0365(8) Uani 1 1 d . U . . .
H21A H 0.609846 0.543357 1.003591 0.055 Uiso 1 1 calc R U . . .
H21B H 0.525956 0.612521 1.040825 0.055 Uiso 1 1 calc R U . . .
H21C H 0.634590 0.655555 1.014738 0.055 Uiso 1 1 calc R U . . .
F1 F 0.15575(14) 0.29662(12) 0.63561(11) 0.0330(4) Uani 1 1 d . U . . .
F2 F 0.00547(16) 0.15575(14) 0.62268(13) 0.0506(6) Uani 1 1 d . U . . .
F3 F -0.07764(14) 0.07240(11) 0.45257(14) 0.0436(5) Uani 1 1 d . U . . .
F4 F -0.01357(14) 0.13354(14) 0.29348(14) 0.0469(5) Uani 1 1 d . U . . .
F5 F 0.13551(15) 0.27473(16) 0.30635(12) 0.0493(6) Uani 1 1 d . U . . .
F13 F 0.22764(12) 0.69671(10) 0.17534(11) 0.0218(4) Uani 1 1 d . U . . .
F14 F 0.12795(13) 0.85084(11) 0.08226(11) 0.0285(4) Uani 1 1 d . U . . .
F15 F 0.10434(15) 1.01232(11) 0.18009(13) 0.0389(5) Uani 1 1 d . U . . .
F16 F 0.18547(16) 1.02076(12) 0.37187(14) 0.0467(5) Uani 1 1 d . U . . .
F17 F 0.28360(14) 0.86663(12) 0.46542(12) 0.0352(4) Uani 1 1 d . U . . .
H4 H 0.435(3) 0.365(2) 0.356(2) 0.034(10) Uiso 1 1 d . . . . .
H5 H 0.519(3) 0.478(2) 0.695(3) 0.049(12) Uiso 1 1 d . . . . .
H6 H 0.584(2) 0.591(2) 0.805(2) 0.024(9) Uiso 1 1 d . . . . .
H7 H 0.488(3) 0.672(2) 0.896(2) 0.030(10) Uiso 1 1 d . . . . .
Ni1 Ni 0.47541(3) 0.39766(2) 0.53349(2) 0.01555(10) Uani 1 1 d . U . . .
O1 O 0.33398(14) 0.33026(12) 0.52621(12) 0.0171(4) Uani 1 1 d . U . . .
O2 O 0.39666(13) 0.51435(12) 0.46960(12) 0.0161(4) Uani 1 1 d . U . . .
O3 O 0.42110(14) 0.70474(12) 0.40521(13) 0.0194(4) Uani 1 1 d . U . . .
O4 O 0.47553(16) 0.33713(14) 0.39982(15) 0.0218(5) Uani 1 1 d . U . . .
O5 O 0.46709(17) 0.44923(15) 0.66751(14) 0.0253(5) Uani 1 1 d . U . . .
O6 O 0.61844(17) 0.56959(15) 0.76718(15) 0.0264(5) Uani 1 1 d . U . . .
O7 O 0.51832(17) 0.62218(15) 0.90200(14) 0.0266(5) Uani 1 1 d . 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
C1 F1 1.339(3) . ?
C1 C6 1.379(4) . ?
C1 C2 1.381(4) . ?
C2 F2 1.336(3) . ?
C2 C3 1.376(4) . ?
C3 F3 1.342(3) . ?
C3 C4 1.368(4) . ?
C4 F4 1.341(3) . ?
C4 C5 1.377(4) . ?
C5 F5 1.342(3) . ?
C5 C6 1.382(4) . ?
C6 C7 1.511(4) . ?
C7 O1 1.273(3) . ?
C7 C8 1.385(4) . ?
C8 C9 1.417(4) . ?
C8 H8 0.9500 . ?
C9 O2 1.294(3) . ?
C9 C10 1.431(3) . ?
C10 C11 1.373(4) . ?
C10 H10 0.9500 . ?
C11 O3 1.294(3) . ?
C11 C12 1.510(4) . ?
C12 C13 1.384(4) . ?
C12 C17 1.386(4) . ?
C13 F13 1.347(3) . ?
C13 C14 1.376(4) . ?
C14 F14 1.343(3) . ?
C14 C15 1.377(4) . ?
C15 F15 1.338(3) . ?
C15 C16 1.370(4) . ?
C16 F16 1.346(3) . ?
C16 C17 1.378(4) . ?
C17 F17 1.347(3) . ?
C18 O4 1.438(3) . ?
C18 H18A 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18B 0.9800 . ?
C19 O5 1.404(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 O6 1.439(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 O7 1.426(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
Ni1 O1 1.9832(18) . ?
Ni1 O3 2.0000(17) 3_666 ?
Ni1 O2 2.0197(17) . ?
Ni1 O2 2.0234(17) 3_666 ?
Ni1 O5 2.081(2) . ?
Ni1 O4 2.100(2) . ?
O4 H4 0.82(3) . ?
O5 H5 0.79(4) . ?
O6 H6 0.82(3) . ?
O7 H7 0.79(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
F1 C1 C6 119.5(2) . . ?
F1 C1 C2 118.1(2) . . ?
C6 C1 C2 122.5(3) . . ?
F2 C2 C3 119.9(3) . . ?
F2 C2 C1 120.9(3) . . ?
C3 C2 C1 119.1(3) . . ?
F3 C3 C4 120.3(3) . . ?
F3 C3 C2 119.5(3) . . ?
C4 C3 C2 120.2(3) . . ?
F4 C4 C3 120.2(3) . . ?
F4 C4 C5 120.5(3) . . ?
C3 C4 C5 119.3(3) . . ?
F5 C5 C4 118.1(3) . . ?
F5 C5 C6 119.2(3) . . ?
C4 C5 C6 122.6(3) . . ?
C1 C6 C5 116.3(2) . . ?
C1 C6 C7 121.4(2) . . ?
C5 C6 C7 122.1(2) . . ?
O1 C7 C8 129.0(2) . . ?
O1 C7 C6 113.0(2) . . ?
C8 C7 C6 118.0(2) . . ?
C7 C8 C9 126.4(2) . . ?
C7 C8 H8 116.8 . . ?
C9 C8 H8 116.8 . . ?
O2 C9 C8 120.7(2) . . ?
O2 C9 C10 119.9(2) . . ?
C8 C9 C10 119.4(2) . . ?
C11 C10 C9 126.5(2) . . ?
C11 C10 H10 116.8 . . ?
C9 C10 H10 116.8 . . ?
O3 C11 C10 129.3(2) . . ?
O3 C11 C12 113.6(2) . . ?
C10 C11 C12 117.1(2) . . ?
C13 C12 C17 116.4(2) . . ?
C13 C12 C11 122.4(2) . . ?
C17 C12 C11 121.1(2) . . ?
F13 C13 C14 117.9(2) . . ?
F13 C13 C12 119.5(2) . . ?
C14 C13 C12 122.6(2) . . ?
F14 C14 C13 120.8(2) . . ?
F14 C14 C15 120.0(2) . . ?
C13 C14 C15 119.2(3) . . ?
F15 C15 C16 120.4(3) . . ?
F15 C15 C14 119.6(3) . . ?
C16 C15 C14 120.0(3) . . ?
F16 C16 C15 120.2(3) . . ?
F16 C16 C17 120.0(3) . . ?
C15 C16 C17 119.8(3) . . ?
F17 C17 C16 118.4(2) . . ?
F17 C17 C12 119.6(2) . . ?
C16 C17 C12 122.0(3) . . ?
O4 C18 H18A 109.5 . . ?
O4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
O4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18C C18 H18B 109.5 . . ?
O5 C19 H19A 109.5 . . ?
O5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O6 C20 H20A 109.5 . . ?
O6 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O6 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 H21A 109.5 . . ?
O7 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O7 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O1 Ni1 O3 99.49(7) . 3_666 ?
O1 Ni1 O2 91.18(7) . . ?
O3 Ni1 O2 169.27(7) 3_666 . ?
O1 Ni1 O2 170.04(7) . 3_666 ?
O3 Ni1 O2 90.47(7) 3_666 3_666 ?
O2 Ni1 O2 78.87(7) . 3_666 ?
O1 Ni1 O5 89.47(8) . . ?
O3 Ni1 O5 89.86(8) 3_666 . ?
O2 Ni1 O5 91.36(8) . . ?
O2 Ni1 O5 90.45(8) 3_666 . ?
O1 Ni1 O4 86.43(7) . . ?
O3 Ni1 O4 89.18(8) 3_666 . ?
O2 Ni1 O4 90.38(8) . . ?
O2 Ni1 O4 93.88(7) 3_666 . ?
O5 Ni1 O4 175.57(8) . . ?
C7 O1 Ni1 123.53(16) . . ?
C9 O2 Ni1 128.62(16) . . ?
C9 O2 Ni1 130.03(16) . 3_666 ?
Ni1 O2 Ni1 101.13(7) . 3_666 ?
C11 O3 Ni1 123.36(16) . 3_666 ?
C18 O4 Ni1 121.12(17) . . ?
C18 O4 H4 108(2) . . ?
Ni1 O4 H4 113(2) . . ?
C19 O5 Ni1 125.6(2) . . ?
C19 O5 H5 111(3) . . ?
Ni1 O5 H5 116(3) . . ?
C20 O6 H6 112(2) . . ?
C21 O7 H7 112(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C1 C2 F2 0.6(4) . . . . ?
C6 C1 C2 F2 179.9(3) . . . . ?
F1 C1 C2 C3 -179.1(2) . . . . ?
C6 C1 C2 C3 0.1(4) . . . . ?
F2 C2 C3 F3 -0.5(4) . . . . ?
C1 C2 C3 F3 179.2(2) . . . . ?
F2 C2 C3 C4 179.3(3) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
F3 C3 C4 F4 -0.1(4) . . . . ?
C2 C3 C4 F4 -179.9(2) . . . . ?
F3 C3 C4 C5 -179.7(2) . . . . ?
C2 C3 C4 C5 0.5(4) . . . . ?
F4 C4 C5 F5 -0.9(4) . . . . ?
C3 C4 C5 F5 178.7(3) . . . . ?
F4 C4 C5 C6 -178.8(2) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
F1 C1 C6 C5 -179.7(2) . . . . ?
C2 C1 C6 C5 1.1(4) . . . . ?
F1 C1 C6 C7 5.5(4) . . . . ?
C2 C1 C6 C7 -173.8(3) . . . . ?
F5 C5 C6 C1 -179.5(2) . . . . ?
C4 C5 C6 C1 -1.6(4) . . . . ?
F5 C5 C6 C7 -4.7(4) . . . . ?
C4 C5 C6 C7 173.3(2) . . . . ?
C1 C6 C7 O1 65.4(3) . . . . ?
C5 C6 C7 O1 -109.2(3) . . . . ?
C1 C6 C7 C8 -115.7(3) . . . . ?
C5 C6 C7 C8 69.7(3) . . . . ?
O1 C7 C8 C9 3.1(5) . . . . ?
C6 C7 C8 C9 -175.6(2) . . . . ?
C7 C8 C9 O2 1.0(4) . . . . ?
C7 C8 C9 C10 179.7(3) . . . . ?
O2 C9 C10 C11 -1.0(4) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 O3 -0.7(5) . . . . ?
C9 C10 C11 C12 179.6(2) . . . . ?
O3 C11 C12 C13 108.2(3) . . . . ?
C10 C11 C12 C13 -72.0(3) . . . . ?
O3 C11 C12 C17 -68.5(3) . . . . ?
C10 C11 C12 C17 111.2(3) . . . . ?
C17 C12 C13 F13 177.2(2) . . . . ?
C11 C12 C13 F13 0.3(4) . . . . ?
C17 C12 C13 C14 -0.8(4) . . . . ?
C11 C12 C13 C14 -177.7(2) . . . . ?
F13 C13 C14 F14 0.6(4) . . . . ?
C12 C13 C14 F14 178.7(2) . . . . ?
F13 C13 C14 C15 -178.4(2) . . . . ?
C12 C13 C14 C15 -0.3(4) . . . . ?
F14 C14 C15 F15 1.7(4) . . . . ?
C13 C14 C15 F15 -179.3(2) . . . . ?
F14 C14 C15 C16 -177.8(3) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
F15 C15 C16 F16 0.5(4) . . . . ?
C14 C15 C16 F16 179.9(3) . . . . ?
F15 C15 C16 C17 179.6(3) . . . . ?
C14 C15 C16 C17 -1.0(4) . . . . ?
F16 C16 C17 F17 0.8(4) . . . . ?
C15 C16 C17 F17 -178.3(3) . . . . ?
F16 C16 C17 C12 178.9(3) . . . . ?
C15 C16 C17 C12 -0.2(5) . . . . ?
C13 C12 C17 F17 179.1(2) . . . . ?
C11 C12 C17 F17 -3.9(4) . . . . ?
C13 C12 C17 C16 1.0(4) . . . . ?
C11 C12 C17 C16 178.0(3) . . . . ?
C8 C7 O1 Ni1 -8.9(4) . . . . ?
C6 C7 O1 Ni1 169.81(15) . . . . ?
C8 C9 O2 Ni1 1.8(3) . . . . ?
C10 C9 O2 Ni1 -176.89(17) . . . . ?
C8 C9 O2 Ni1 175.40(17) . . . 3_666 ?
C10 C9 O2 Ni1 -3.3(3) . . . 3_666 ?
C10 C11 O3 Ni1 6.1(4) . . . 3_666 ?
C12 C11 O3 Ni1 -174.19(16) . . . 3_666 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576
C19 H19A F1 0.98 2.61 3.527(4) 156.5 .
C20 H20B F3 0.98 2.64 3.270(3) 122.5 4_666
C21 H21C O1 0.98 2.56 3.355(4) 137.8 2_656
O4 H4 O6 0.82(3) 1.97(3) 2.760(3) 162(3) 3_666
O5 H5 O6 0.79(4) 1.93(4) 2.697(3) 166(4) .
O6 H6 O7 0.82(3) 1.82(3) 2.629(3) 170(3) .
O7 H7 O3 0.79(3) 1.94(3) 2.712(3) 170(3) 4_576

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.068

