# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_lls-l3-ni(no3)3-1
_database_code_depnum_ccdc_archive 'CCDC 1946861'
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-28
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C42 H32 F6 N4 Ni O16'
_chemical_formula_sum            'C42 H32 F6 N4 Ni O16'
_chemical_formula_weight         1021.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6971(4)
_cell_length_b                   11.4942(9)
_cell_length_c                   12.0058(10)
_cell_angle_alpha                71.997(7)
_cell_angle_beta                 87.716(6)
_cell_angle_gamma                77.460(6)
_cell_volume                     985.65(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2391
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2560
_cell_measurement_theta_min      3.5540
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             522
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12325
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.291
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.8957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -40.00  50.00   1.00   20.00    --  -18.55  57.00-180.00   90
  2  ω    -91.00   7.00   1.00   20.00    --  -18.55 -38.00   0.00   98
  3  ω    -89.00  12.00   1.00   20.00    --  -18.55 -77.00  60.00  101
  4  ω    -20.00  61.00   1.00   20.00    --   18.86 -99.00-150.00   81
  5  ω     -3.00  88.00   1.00   20.00    --   18.86  57.00  60.00   91
  6  ω    -51.00  49.00   1.00   20.00    --   18.86 -77.00 -60.00  100
  7  ω     35.00  95.00   1.00   20.00    --   18.86 178.00 -60.00   60
  8  ω    -25.00   0.00   1.00   20.00    --   18.86  19.00 -60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0790716000
_diffrn_orient_matrix_UB_12      -0.0224089000
_diffrn_orient_matrix_UB_13      0.0165805000
_diffrn_orient_matrix_UB_21      0.0453285000
_diffrn_orient_matrix_UB_22      -0.0607255000
_diffrn_orient_matrix_UB_23      0.0000125000
_diffrn_orient_matrix_UB_31      0.0247558000
_diffrn_orient_matrix_UB_32      -0.0150198000
_diffrn_orient_matrix_UB_33      0.0598954000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2956
_reflns_number_total             4019
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4019
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0995
_refine_ls_R_factor_gt           0.0727
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1234P)²+1.5221P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2049
_refine_ls_wR_factor_ref         0.2297
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ni1 Ni 0.5000 0.5000 0.5000 0.0345(3) Uani 1 2 d S . P . .
F1 F 0.7084(14) -0.5030(6) 0.9526(7) 0.176(3) Uani 1 1 d . U . . .
F2 F 0.8930(15) -0.4049(8) 0.9963(10) 0.219(4) Uani 1 1 d . U . . .
F3 F 0.6398(14) -0.3974(7) 1.0723(6) 0.181(3) Uani 1 1 d . U . . .
O1 O 0.7137(4) 0.3514(3) 0.5170(3) 0.0376(8) Uani 1 1 d . . . . .
O2 O 1.2933(4) 0.0349(3) 0.5508(3) 0.0446(9) Uani 1 1 d . . . . .
O3 O 1.2357(4) -0.1725(3) 0.6913(3) 0.0468(9) Uani 1 1 d . . . . .
O4 O 0.6966(5) -0.1805(3) 0.8918(3) 0.0504(9) Uani 1 1 d . . . . .
O5 O 0.3817(5) -0.1681(4) 0.9813(3) 0.0586(11) Uani 1 1 d . . . . .
O6 O 0.3869(5) 0.4348(3) 0.3806(4) 0.0573(10) Uani 1 1 d . . . . .
O7 O 0.1356(7) 0.4330(5) 0.3139(6) 0.0968(19) Uani 1 1 d . . . . .
O8 O 0.2252(8) 0.5998(5) 0.2661(5) 0.0903(17) Uani 1 1 d . . . . .
N1 N 0.4109(5) 0.3656(3) 0.6283(3) 0.0355(9) Uani 1 1 d . . . . .
N2 N 0.2457(6) 0.4875(4) 0.3221(4) 0.0466(10) Uani 1 1 d . . . . .
C1 C 0.2510(6) 0.3747(5) 0.6774(5) 0.0430(12) Uani 1 1 d . . . . .
H1 H 0.1697 0.4512 0.6565 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2054(6) 0.2723(5) 0.7582(5) 0.0450(12) Uani 1 1 d . . . . .
H2 H 0.0938 0.2806 0.7912 0.054 Uiso 1 1 calc R U . . .
C3 C 0.3240(6) 0.1567(4) 0.7912(4) 0.0372(10) Uani 1 1 d . . . . .
C4 C 0.2823(7) 0.0495(5) 0.8728(4) 0.0434(12) Uani 1 1 d . . . . .
H4 H 0.1709 0.0538 0.9063 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2121(8) -0.1705(6) 1.0323(5) 0.0576(15) Uani 1 1 d . . . . .
H5A H 0.1221 -0.1465 0.9715 0.086 Uiso 1 1 calc R U . . .
H5B H 0.1881 -0.1129 1.0772 0.086 Uiso 1 1 calc R U . . .
H5C H 0.2115 -0.2535 1.0826 0.086 Uiso 1 1 calc R U . . .
C6 C 0.4048(7) -0.0599(5) 0.9025(4) 0.0438(12) Uani 1 1 d . . . . .
C7 C 0.5774(7) -0.0699(4) 0.8501(4) 0.0369(10) Uani 1 1 d . U . . .
C8 C 0.6561(10) -0.2907(6) 0.8728(6) 0.0684(17) Uani 1 1 d . U . . .
H8A H 0.5284 -0.2796 0.8633 0.082 Uiso 1 1 calc R U . . .
H8B H 0.7113 -0.3026 0.8019 0.082 Uiso 1 1 calc R U . . .
C9 C 0.7198(19) -0.3945(10) 0.9677(11) 0.119(3) Uani 1 1 d . U . . .
C10 C 0.6262(6) 0.0322(4) 0.7686(4) 0.0306(9) Uani 1 1 d . . . . .
C11 C 0.7999(6) 0.0312(4) 0.7117(4) 0.0299(9) Uani 1 1 d . . . . .
C12 C 0.9391(6) -0.0739(4) 0.7321(4) 0.0329(10) Uani 1 1 d . . . . .
H12 H 0.9233 -0.1486 0.7857 0.040 Uiso 1 1 calc R U . . .
C13 C 1.0990(6) -0.0723(4) 0.6764(4) 0.0345(10) Uani 1 1 d . . . . .
C14 C 1.2055(8) -0.2939(4) 0.7496(5) 0.0506(13) Uani 1 1 d . . . . .
H14A H 1.1033 -0.3056 0.7145 0.076 Uiso 1 1 calc R U . . .
H14B H 1.1848 -0.3024 0.8309 0.076 Uiso 1 1 calc R U . . .
H14C H 1.3080 -0.3559 0.7430 0.076 Uiso 1 1 calc R U . . .
C15 C 1.3280(6) 0.1470(4) 0.4693(5) 0.0421(11) Uani 1 1 d . . . . .
H15A H 1.2475 0.1734 0.4028 0.063 Uiso 1 1 calc R U . . .
H15B H 1.4484 0.1315 0.4440 0.063 Uiso 1 1 calc R U . . .
H15C H 1.3115 0.2116 0.5063 0.063 Uiso 1 1 calc R U . . .
C16 C 1.1305(6) 0.0413(4) 0.5976(4) 0.0313(9) Uani 1 1 d . . . . .
C17 C 0.9953(6) 0.1451(4) 0.5742(4) 0.0307(9) Uani 1 1 d . . . . .
H17 H 1.0126 0.2197 0.5210 0.037 Uiso 1 1 calc R U . . .
C18 C 0.8314(6) 0.1418(4) 0.6283(4) 0.0296(9) Uani 1 1 d . . . . .
C19 C 0.6957(6) 0.2562(4) 0.5949(4) 0.0302(9) Uani 1 1 d . . . . .
C20 C 0.5266(5) 0.2563(4) 0.6586(4) 0.0288(9) Uani 1 1 d . . . . .
C21 C 0.4952(6) 0.1473(4) 0.7403(4) 0.0307(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 O1 2.063(3) . ?
Ni1 O1 2.063(3) 2_666 ?
Ni1 O6 2.103(4) 2_666 ?
Ni1 O6 2.103(4) . ?
Ni1 N1 2.034(4) 2_666 ?
Ni1 N1 2.034(4) . ?
F1 C9 1.336(11) . ?
F2 C9 1.361(15) . ?
F3 C9 1.370(14) . ?
O1 C19 1.230(5) . ?
O2 C15 1.428(5) . ?
O2 C16 1.349(5) . ?
O3 C13 1.351(5) . ?
O3 C14 1.420(6) . ?
O4 C7 1.358(6) . ?
O4 C8 1.452(7) . ?
O5 C5 1.422(7) . ?
O5 C6 1.352(6) . ?
O6 N2 1.246(6) . ?
O7 N2 1.182(6) . ?
O8 N2 1.236(6) . ?
N1 C1 1.341(6) . ?
N1 C20 1.327(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.377(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(7) . ?
C3 C4 1.408(7) . ?
C3 C21 1.427(6) . ?
C4 H4 0.9300 . ?
C4 C6 1.354(7) . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.444(7) . ?
C7 C10 1.389(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.383(13) . ?
C10 C11 1.476(6) . ?
C10 C21 1.433(6) . ?
C11 C12 1.394(6) . ?
C11 C18 1.416(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(7) . ?
C13 C16 1.419(6) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.365(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.399(6) . ?
C18 C19 1.447(6) . ?
C19 C20 1.483(6) . ?
C20 C21 1.394(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Ni1 O1 180.0 2_666 . ?
O1 Ni1 O6 92.89(14) 2_666 . ?
O1 Ni1 O6 87.11(14) . . ?
O1 Ni1 O6 87.11(14) 2_666 2_666 ?
O1 Ni1 O6 92.89(14) . 2_666 ?
O6 Ni1 O6 180.00(16) . 2_666 ?
N1 Ni1 O1 99.78(13) . 2_666 ?
N1 Ni1 O1 99.78(13) 2_666 . ?
N1 Ni1 O1 80.22(13) . . ?
N1 Ni1 O1 80.22(13) 2_666 2_666 ?
N1 Ni1 O6 93.53(16) . 2_666 ?
N1 Ni1 O6 93.53(16) 2_666 . ?
N1 Ni1 O6 86.47(16) . . ?
N1 Ni1 O6 86.47(16) 2_666 2_666 ?
N1 Ni1 N1 180.0 2_666 . ?
C19 O1 Ni1 112.9(3) . . ?
C16 O2 C15 117.2(4) . . ?
C13 O3 C14 118.9(4) . . ?
C7 O4 C8 117.9(5) . . ?
C6 O5 C5 118.0(5) . . ?
N2 O6 Ni1 126.0(3) . . ?
C1 N1 Ni1 127.6(3) . . ?
C20 N1 Ni1 112.9(3) . . ?
C20 N1 C1 119.3(4) . . ?
O7 N2 O6 122.5(5) . . ?
O7 N2 O8 119.1(5) . . ?
O8 N2 O6 118.2(5) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 120.9(4) . . ?
C2 C1 H1 119.5 . . ?
C1 C2 H2 119.5 . . ?
C1 C2 C3 120.9(5) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 122.7(5) . . ?
C2 C3 C21 118.2(4) . . ?
C4 C3 C21 119.0(4) . . ?
C3 C4 H4 120.1 . . ?
C6 C4 C3 119.8(5) . . ?
C6 C4 H4 120.1 . . ?
O5 C5 H5A 109.5 . . ?
O5 C5 H5B 109.5 . . ?
O5 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O5 C6 C4 125.2(5) . . ?
O5 C6 C7 113.5(4) . . ?
C4 C6 C7 121.3(4) . . ?
O4 C7 C6 117.1(4) . . ?
O4 C7 C10 120.9(4) . . ?
C10 C7 C6 121.7(4) . . ?
O4 C8 H8A 109.8 . . ?
O4 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 O4 109.3(7) . . ?
C9 C8 H8A 109.8 . . ?
C9 C8 H8B 109.8 . . ?
F1 C9 F2 106.8(11) . . ?
F1 C9 F3 104.2(10) . . ?
F1 C9 C8 113.9(10) . . ?
F2 C9 F3 101.5(11) . . ?
F2 C9 C8 112.7(10) . . ?
F3 C9 C8 116.5(10) . . ?
C7 C10 C11 125.5(4) . . ?
C7 C10 C21 115.9(4) . . ?
C21 C10 C11 118.6(4) . . ?
C12 C11 C10 124.5(4) . . ?
C12 C11 C18 115.8(4) . . ?
C18 C11 C10 119.7(4) . . ?
C11 C12 H12 118.4 . . ?
C13 C12 C11 123.1(4) . . ?
C13 C12 H12 118.4 . . ?
O3 C13 C12 125.1(4) . . ?
O3 C13 C16 114.9(4) . . ?
C12 C13 C16 119.9(4) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 C13 115.8(4) . . ?
O2 C16 C17 126.0(4) . . ?
C17 C16 C13 118.2(4) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C11 C18 C19 121.6(4) . . ?
C17 C18 C11 121.4(4) . . ?
C17 C18 C19 116.9(4) . . ?
O1 C19 C18 123.5(4) . . ?
O1 C19 C20 119.3(4) . . ?
C18 C19 C20 117.2(4) . . ?
N1 C20 C19 114.5(4) . . ?
N1 C20 C21 124.5(4) . . ?
C21 C20 C19 120.9(4) . . ?
C3 C21 C10 122.4(4) . . ?
C20 C21 C3 116.1(4) . . ?
C20 C21 C10 121.6(4) . . ?

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
C1 H1 O7 0.93 2.51 3.319(7) 145.9 2_566
C2 H2 O8 0.93 2.54 3.306(8) 139.3 2_566
C5 H5C O8 0.96 2.31 3.192(7) 151.8 1_546
C8 H8A O5 0.97 2.30 2.787(8) 110.2 .
C8 H8B O7 0.97 2.44 3.333(9) 152.7 2_656
C12 H12 O4 0.93 2.15 2.814(6) 127.7 .
C14 H14A O7 0.96 2.68 3.573(7) 155.4 2_656
C15 H15B O2 0.96 2.43 3.246(6) 142.8 2_856

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
Ni1 O1 C19 C18 -176.4(3) . . . . ?
Ni1 O1 C19 C20 4.0(5) . . . . ?
Ni1 O6 N2 O7 -133.7(5) . . . . ?
Ni1 O6 N2 O8 49.9(7) . . . . ?
Ni1 N1 C1 C2 175.5(4) . . . . ?
Ni1 N1 C20 C19 1.2(5) . . . . ?
Ni1 N1 C20 C21 -176.8(3) . . . . ?
O1 C19 C20 N1 -3.6(6) . . . . ?
O1 C19 C20 C21 174.5(4) . . . . ?
O2 C16 C17 C18 -179.5(4) . . . . ?
O3 C13 C16 O2 -1.7(6) . . . . ?
O3 C13 C16 C17 177.0(4) . . . . ?
O4 C7 C10 C11 5.4(7) . . . . ?
O4 C7 C10 C21 -173.6(4) . . . . ?
O4 C8 C9 F1 -172.3(9) . . . . ?
O4 C8 C9 F2 -50.5(13) . . . . ?
O4 C8 C9 F3 66.3(13) . . . . ?
O5 C6 C7 O4 -5.0(7) . . . . ?
O5 C6 C7 C10 -178.9(4) . . . . ?
N1 C1 C2 C3 0.0(8) . . . . ?
N1 C20 C21 C3 1.4(7) . . . . ?
N1 C20 C21 C10 179.8(4) . . . . ?
C1 N1 C20 C19 177.4(4) . . . . ?
C1 N1 C20 C21 -0.6(7) . . . . ?
C1 C2 C3 C4 -179.5(5) . . . . ?
C1 C2 C3 C21 0.9(7) . . . . ?
C2 C3 C4 C6 -179.0(5) . . . . ?
C2 C3 C21 C10 -179.8(4) . . . . ?
C2 C3 C21 C20 -1.5(6) . . . . ?
C3 C4 C6 O5 178.6(5) . . . . ?
C3 C4 C6 C7 -1.3(8) . . . . ?
C4 C3 C21 C10 0.6(7) . . . . ?
C4 C3 C21 C20 178.9(4) . . . . ?
C4 C6 C7 O4 175.0(5) . . . . ?
C4 C6 C7 C10 1.0(8) . . . . ?
C5 O5 C6 C4 4.1(8) . . . . ?
C5 O5 C6 C7 -175.9(5) . . . . ?
C6 C7 C10 C11 179.2(4) . . . . ?
C6 C7 C10 C21 0.1(7) . . . . ?
C7 O4 C8 C9 -145.6(8) . . . . ?
C7 C10 C11 C12 0.4(7) . . . . ?
C7 C10 C11 C18 178.9(4) . . . . ?
C7 C10 C21 C3 -0.9(6) . . . . ?
C7 C10 C21 C20 -179.1(4) . . . . ?
C8 O4 C7 C6 65.8(6) . . . . ?
C8 O4 C7 C10 -120.2(5) . . . . ?
C10 C11 C12 C13 179.1(4) . . . . ?
C10 C11 C18 C17 178.8(4) . . . . ?
C10 C11 C18 C19 -1.4(6) . . . . ?
C11 C10 C21 C3 -180.0(4) . . . . ?
C11 C10 C21 C20 1.8(6) . . . . ?
C11 C12 C13 O3 -178.3(4) . . . . ?
C11 C12 C13 C16 2.6(7) . . . . ?
C11 C18 C19 O1 -174.7(4) . . . . ?
C11 C18 C19 C20 4.9(6) . . . . ?
C12 C11 C18 C17 -2.5(6) . . . . ?
C12 C11 C18 C19 177.2(4) . . . . ?
C12 C13 C16 O2 177.5(4) . . . . ?
C12 C13 C16 C17 -3.8(7) . . . . ?
C13 C16 C17 C18 1.9(7) . . . . ?
C14 O3 C13 C12 13.0(7) . . . . ?
C14 O3 C13 C16 -167.8(4) . . . . ?
C15 O2 C16 C13 178.7(4) . . . . ?
C15 O2 C16 C17 0.1(7) . . . . ?
C16 C17 C18 C11 1.3(7) . . . . ?
C16 C17 C18 C19 -178.4(4) . . . . ?
C17 C18 C19 O1 5.0(7) . . . . ?
C17 C18 C19 C20 -175.4(4) . . . . ?
C18 C11 C12 C13 0.5(7) . . . . ?
C18 C19 C20 N1 176.7(4) . . . . ?
C18 C19 C20 C21 -5.2(6) . . . . ?
C19 C20 C21 C3 -176.5(4) . . . . ?
C19 C20 C21 C10 1.9(6) . . . . ?
C20 N1 C1 C2 -0.2(7) . . . . ?
C21 C3 C4 C6 0.6(7) . . . . ?
C21 C10 C11 C12 179.4(4) . . . . ?
C21 C10 C11 C18 -2.0(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.371
_oxdiff_exptl_absorpt_empirical_full_min 0.801
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.789
_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.
;
_shelxl_version_number           2013-2
####################################################################### 
# 
# 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_lls-l3-cuaaaa
_database_code_depnum_ccdc_archive 'CCDC 1946862'
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C42 H32 Cu F6 N4 O16'
_chemical_formula_sum            'C42 H32 Cu F6 N4 O16'
_chemical_formula_weight         1026.27
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8601(8)
_cell_length_b                   11.264(3)
_cell_length_c                   11.987(3)
_cell_angle_alpha                73.43(2)
_cell_angle_beta                 85.658(16)
_cell_angle_gamma                76.835(15)
_cell_volume                     990.4(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1646
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.1850
_cell_measurement_theta_min      3.5330
_shelx_estimated_absorpt_T_max   0.895
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.665
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97805
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             523
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1152
_diffrn_reflns_av_unetI/netI     0.1830
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11484
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         3.540
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6296
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -61.00  39.00   1.00   12.50    --   10.68 -57.00 -30.00  100
  2  ω    -22.00  87.00   1.00   12.50    --   10.68  77.00-120.00  109
  3  ω    -17.00  84.00   1.00   12.50    --   10.68  57.00 120.00  101
  4  ω     34.00  98.00   1.00   12.50    --   10.68-178.00 -60.00   64
  5  ω    -17.00  10.00   1.00   12.50    --   10.68  57.00   0.00   27
  6  ω   -101.00 -35.00   1.00   12.50    --  -11.93-178.00   0.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0132500000
_diffrn_orient_matrix_UB_12      0.0379289000
_diffrn_orient_matrix_UB_13      -0.0583654000
_diffrn_orient_matrix_UB_21      -0.0883580000
_diffrn_orient_matrix_UB_22      -0.0058765000
_diffrn_orient_matrix_UB_23      0.0039933000
_diffrn_orient_matrix_UB_31      -0.0246443000
_diffrn_orient_matrix_UB_32      0.0552615000
_diffrn_orient_matrix_UB_33      0.0197364000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1639
_reflns_number_total             3637
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1823
_refine_ls_R_factor_gt           0.0801
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0706P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1620
_refine_ls_wR_factor_ref         0.2273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C14(H14), C2(H2), C17(H17), C4(H4)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C6(H6A,H6B,H6C), C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.0000 0.0000 0.0434(5) Uani 1 2 d S T P . .
F1 F 0.3812(11) 0.1066(6) 0.5013(8) 0.159(3) Uani 1 1 d . . . . .
F2 F 0.2159(11) -0.0024(5) 0.4597(6) 0.132(3) Uani 1 1 d . . . . .
F3 F 0.1261(11) 0.1143(6) 0.5744(6) 0.132(3) Uani 1 1 d . . . . .
O7 O -0.1147(7) 0.9304(5) -0.1437(5) 0.0578(15) Uani 1 1 d . . . . .
O1 O 0.2120(6) 0.8568(4) 0.0113(4) 0.0407(12) Uani 1 1 d . . . . .
O2 O 0.7893(6) 0.5377(4) 0.0488(4) 0.0446(13) Uani 1 1 d . . . . .
O3 O 0.7321(6) 0.3313(4) 0.1911(4) 0.0474(13) Uani 1 1 d . . . . .
O4 O 0.1881(6) 0.3273(4) 0.3886(4) 0.0487(13) Uani 1 1 d . . . . .
O5 O -0.1242(7) 0.3419(5) 0.4792(4) 0.0554(15) Uani 1 1 d . . . . .
O8 O -0.3765(8) 0.9347(5) -0.1839(6) 0.084(2) Uani 1 1 d . . . . .
O6 O -0.2805(8) 1.1045(5) -0.2381(5) 0.0723(18) Uani 1 1 d . . . . .
N1 N -0.0915(8) 0.8700(5) 0.1192(5) 0.0382(14) Uani 1 1 d . . . . .
N2 N -0.2589(9) 0.9908(6) -0.1881(6) 0.0457(16) Uani 1 1 d . . . . .
C3 C -0.1786(9) 0.6635(7) 0.2833(6) 0.0404(18) Uani 1 1 d . . . . .
C18 C 0.8276(9) 0.6500(6) -0.0326(6) 0.0449(19) Uani 1 1 d . . . . .
H18A H 0.7525 0.6748 -0.0986 0.067 Uiso 1 1 calc GR . . . .
H18B H 0.9473 0.6328 -0.0579 0.067 Uiso 1 1 calc GR . . . .
H18C H 0.8085 0.7172 0.0043 0.067 Uiso 1 1 calc GR . . . .
C1 C -0.2506(9) 0.8805(7) 0.1670(6) 0.0440(19) Uani 1 1 d . . . . .
H1 H -0.3307 0.9575 0.1445 0.053 Uiso 1 1 calc R . . . .
C10 C 0.0264(8) 0.7601(6) 0.1520(6) 0.0317(16) Uani 1 1 d . . . . .
C14 C 0.4343(9) 0.4310(6) 0.2297(6) 0.0340(16) Uani 1 1 d . . . . .
H14 H 0.4178 0.3565 0.2834 0.041 Uiso 1 1 calc R . . . .
C11 C 0.1926(9) 0.7614(6) 0.0912(5) 0.0304(16) Uani 1 1 d . . . . .
C13 C 0.2946(9) 0.5361(6) 0.2078(6) 0.0317(16) Uani 1 1 d . . . . .
C2 C -0.3000(10) 0.7797(7) 0.2494(6) 0.0448(19) Uani 1 1 d . . . . .
H2 H -0.4120 0.7888 0.2817 0.054 Uiso 1 1 calc R . . . .
C15 C 0.5940(10) 0.4322(6) 0.1761(6) 0.0369(17) Uani 1 1 d . . . . .
C7 C 0.0701(9) 0.4374(6) 0.3458(6) 0.0366(17) Uani 1 1 d . . . . .
C6 C -0.2942(11) 0.3406(8) 0.5316(7) 0.062(2) Uani 1 1 d . . . . .
H6A H -0.3792 0.3597 0.4720 0.093 Uiso 1 1 calc GR . . . .
H6B H -0.3228 0.4030 0.5742 0.093 Uiso 1 1 calc GR . . . .
H6C H -0.2945 0.2582 0.5837 0.093 Uiso 1 1 calc GR . . . .
C20 C 0.1547(11) 0.2137(6) 0.3729(7) 0.055(2) Uani 1 1 d . . . . .
H20A H 0.2138 0.1970 0.3032 0.066 Uiso 1 1 calc R . . . .
H20B H 0.0303 0.2223 0.3648 0.066 Uiso 1 1 calc R . . . .
C17 C 0.4926(10) 0.6498(6) 0.0710(6) 0.0400(18) Uani 1 1 d . . . . .
H17 H 0.5109 0.7244 0.0183 0.048 Uiso 1 1 calc R . . . .
C5 C -0.1004(10) 0.4487(7) 0.3977(6) 0.0433(18) Uani 1 1 d . . . . .
C4 C -0.2229(9) 0.5585(7) 0.3661(6) 0.0435(19) Uani 1 1 d . . . . .
H4 H -0.3345 0.5640 0.3988 0.052 Uiso 1 1 calc R . . . .
C9 C -0.0108(9) 0.6539(6) 0.2344(6) 0.0338(16) Uani 1 1 d . . . . .
C8 C 0.1212(9) 0.5381(6) 0.2650(5) 0.0321(16) Uani 1 1 d . . . . .
C21 C 0.2191(17) 0.1107(9) 0.4742(11) 0.087(3) Uani 1 1 d . . . . .
C19 C 0.7016(10) 0.2085(6) 0.2533(7) 0.055(2) Uani 1 1 d . . . . .
H19A H 0.6139 0.1889 0.2142 0.083 Uiso 1 1 calc GR . . . .
H19B H 0.6624 0.2088 0.3311 0.083 Uiso 1 1 calc GR . . . .
H19C H 0.8080 0.1458 0.2561 0.083 Uiso 1 1 calc GR . . . .
C12 C 0.3288(8) 0.6461(6) 0.1243(5) 0.0265(15) Uani 1 1 d . . . . .
C16 C 0.6264(9) 0.5451(6) 0.0957(6) 0.0335(16) 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
Cu1 O7 2.392(5) . ?
Cu1 O7 2.392(5) 2_575 ?
Cu1 O1 2.020(4) . ?
Cu1 O1 2.020(4) 2_575 ?
Cu1 N1 1.958(6) 2_575 ?
Cu1 N1 1.958(6) . ?
F1 C21 1.326(12) . ?
F2 C21 1.340(10) . ?
F3 C21 1.363(12) . ?
O7 N2 1.250(7) . ?
O1 C11 1.249(7) . ?
O2 C18 1.438(7) . ?
O2 C16 1.354(7) . ?
O3 C15 1.361(8) . ?
O3 C19 1.436(7) . ?
O4 C7 1.359(8) . ?
O4 C20 1.428(8) . ?
O5 C6 1.434(8) . ?
O5 C5 1.357(8) . ?
O8 N2 1.223(7) . ?
O6 N2 1.228(7) . ?
N1 C1 1.331(8) . ?
N1 C10 1.342(8) . ?
C3 C2 1.405(9) . ?
C3 C4 1.404(9) . ?
C3 C9 1.396(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C1 H1 0.9300 . ?
C1 C2 1.385(9) . ?
C10 C11 1.449(9) . ?
C10 C9 1.391(9) . ?
C14 H14 0.9300 . ?
C14 C13 1.397(9) . ?
C14 C15 1.368(9) . ?
C11 C12 1.459(9) . ?
C13 C8 1.476(9) . ?
C13 C12 1.419(8) . ?
C2 H2 0.9300 . ?
C15 C16 1.422(9) . ?
C7 C5 1.429(10) . ?
C7 C8 1.382(9) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.449(12) . ?
C17 H17 0.9300 . ?
C17 C12 1.397(9) . ?
C17 C16 1.367(9) . ?
C5 C4 1.358(10) . ?
C4 H4 0.9300 . ?
C9 C8 1.442(9) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O7 Cu1 O7 180.0 2_575 . ?
O1 Cu1 O7 91.17(18) . 2_575 ?
O1 Cu1 O7 88.83(18) 2_575 2_575 ?
O1 Cu1 O7 91.17(18) 2_575 . ?
O1 Cu1 O7 88.83(18) . . ?
O1 Cu1 O1 180.0 . 2_575 ?
N1 Cu1 O7 88.0(2) 2_575 2_575 ?
N1 Cu1 O7 92.0(2) 2_575 . ?
N1 Cu1 O7 88.0(2) . . ?
N1 Cu1 O7 92.0(2) . 2_575 ?
N1 Cu1 O1 82.4(2) 2_575 2_575 ?
N1 Cu1 O1 97.6(2) 2_575 . ?
N1 Cu1 O1 82.4(2) . . ?
N1 Cu1 O1 97.6(2) . 2_575 ?
N1 Cu1 N1 180.0(3) 2_575 . ?
N2 O7 Cu1 118.7(4) . . ?
C11 O1 Cu1 110.8(4) . . ?
C16 O2 C18 117.7(5) . . ?
C15 O3 C19 117.8(5) . . ?
C7 O4 C20 117.9(6) . . ?
C5 O5 C6 118.3(6) . . ?
C1 N1 Cu1 127.5(5) . . ?
C1 N1 C10 119.8(6) . . ?
C10 N1 Cu1 112.7(5) . . ?
O8 N2 O7 119.3(7) . . ?
O8 N2 O6 120.4(7) . . ?
O6 N2 O7 120.2(6) . . ?
C4 C3 C2 121.1(7) . . ?
C9 C3 C2 119.0(7) . . ?
C9 C3 C4 119.9(6) . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.7(7) . . ?
C2 C1 H1 119.2 . . ?
N1 C10 C11 113.9(6) . . ?
N1 C10 C9 122.7(6) . . ?
C9 C10 C11 123.4(6) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C15 C14 C13 123.3(6) . . ?
O1 C11 C10 119.9(6) . . ?
O1 C11 C12 123.0(6) . . ?
C10 C11 C12 117.0(6) . . ?
C14 C13 C8 124.6(6) . . ?
C14 C13 C12 115.2(6) . . ?
C12 C13 C8 120.2(6) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 119.0(7) . . ?
C1 C2 H2 120.5 . . ?
O3 C15 C14 125.6(6) . . ?
O3 C15 C16 114.2(6) . . ?
C14 C15 C16 120.2(6) . . ?
O4 C7 C5 117.2(6) . . ?
O4 C7 C8 120.4(6) . . ?
C8 C7 C5 122.0(6) . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O4 C20 H20A 110.1 . . ?
O4 C20 H20B 110.1 . . ?
O4 C20 C21 107.8(7) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.1 . . ?
C21 C20 H20B 110.1 . . ?
C12 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C16 C17 C12 120.7(6) . . ?
O5 C5 C7 113.8(6) . . ?
O5 C5 C4 125.0(7) . . ?
C4 C5 C7 121.2(7) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.1(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C9 C8 122.3(6) . . ?
C10 C9 C3 117.8(6) . . ?
C10 C9 C8 119.9(6) . . ?
C7 C8 C13 126.0(6) . . ?
C7 C8 C9 115.4(6) . . ?
C9 C8 C13 118.6(6) . . ?
F1 C21 F2 107.4(9) . . ?
F1 C21 F3 104.0(11) . . ?
F1 C21 C20 113.2(10) . . ?
F2 C21 F3 104.6(9) . . ?
F2 C21 C20 111.9(9) . . ?
F3 C21 C20 115.0(9) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C13 C12 C11 120.8(6) . . ?
C17 C12 C11 117.1(6) . . ?
C17 C12 C13 122.2(6) . . ?
O2 C16 C15 115.9(6) . . ?
O2 C16 C17 125.7(6) . . ?
C17 C16 C15 118.3(6) . . ?

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
Cu1 O7 N2 O8 -124.4(6) . . . . ?
Cu1 O7 N2 O6 57.5(8) . . . . ?
Cu1 O1 C11 C10 6.7(7) . . . . ?
Cu1 O1 C11 C12 -176.2(4) . . . . ?
Cu1 N1 C1 C2 178.7(5) . . . . ?
Cu1 N1 C10 C11 -1.0(6) . . . . ?
Cu1 N1 C10 C9 -179.0(5) . . . . ?
O1 C11 C12 C13 -173.8(5) . . . . ?
O1 C11 C12 C17 6.8(9) . . . . ?
O3 C15 C16 O2 -2.0(8) . . . . ?
O3 C15 C16 C17 177.1(6) . . . . ?
O4 C7 C5 O5 -4.3(9) . . . . ?
O4 C7 C5 C4 175.4(6) . . . . ?
O4 C7 C8 C13 6.7(10) . . . . ?
O4 C7 C8 C9 -174.2(5) . . . . ?
O4 C20 C21 F1 -49.6(12) . . . . ?
O4 C20 C21 F2 -171.1(8) . . . . ?
O4 C20 C21 F3 69.8(12) . . . . ?
O5 C5 C4 C3 177.7(6) . . . . ?
N1 C1 C2 C3 0.1(10) . . . . ?
N1 C10 C11 O1 -4.1(8) . . . . ?
N1 C10 C11 C12 178.6(5) . . . . ?
N1 C10 C9 C3 0.4(9) . . . . ?
N1 C10 C9 C8 179.4(5) . . . . ?
C3 C9 C8 C13 179.3(6) . . . . ?
C3 C9 C8 C7 0.2(9) . . . . ?
C18 O2 C16 C15 -179.8(5) . . . . ?
C18 O2 C16 C17 1.2(9) . . . . ?
C1 N1 C10 C11 178.8(5) . . . . ?
C1 N1 C10 C9 0.8(9) . . . . ?
C10 N1 C1 C2 -1.0(9) . . . . ?
C10 C11 C12 C13 3.4(8) . . . . ?
C10 C11 C12 C17 -176.0(5) . . . . ?
C10 C9 C8 C13 0.4(9) . . . . ?
C10 C9 C8 C7 -178.7(6) . . . . ?
C14 C13 C8 C7 -1.3(10) . . . . ?
C14 C13 C8 C9 179.6(6) . . . . ?
C14 C13 C12 C11 178.4(5) . . . . ?
C14 C13 C12 C17 -2.2(9) . . . . ?
C14 C15 C16 O2 178.8(6) . . . . ?
C14 C15 C16 C17 -2.1(9) . . . . ?
C11 C10 C9 C3 -177.4(6) . . . . ?
C11 C10 C9 C8 1.5(9) . . . . ?
C13 C14 C15 O3 -177.5(6) . . . . ?
C13 C14 C15 C16 1.7(10) . . . . ?
C2 C3 C4 C5 -178.9(6) . . . . ?
C2 C3 C9 C10 -1.3(9) . . . . ?
C2 C3 C9 C8 179.8(6) . . . . ?
C15 C14 C13 C8 -179.5(6) . . . . ?
C15 C14 C13 C12 0.5(9) . . . . ?
C7 O4 C20 C21 -145.6(8) . . . . ?
C7 C5 C4 C3 -1.9(11) . . . . ?
C6 O5 C5 C7 -176.3(6) . . . . ?
C6 O5 C5 C4 4.1(10) . . . . ?
C20 O4 C7 C5 65.6(8) . . . . ?
C20 O4 C7 C8 -121.5(7) . . . . ?
C5 C7 C8 C13 179.2(6) . . . . ?
C5 C7 C8 C9 -1.7(9) . . . . ?
C4 C3 C2 C1 -179.7(6) . . . . ?
C4 C3 C9 C10 179.4(6) . . . . ?
C4 C3 C9 C8 0.5(10) . . . . ?
C9 C3 C2 C1 1.0(10) . . . . ?
C9 C3 C4 C5 0.4(10) . . . . ?
C9 C10 C11 O1 173.9(6) . . . . ?
C9 C10 C11 C12 -3.4(9) . . . . ?
C8 C13 C12 C11 -1.7(9) . . . . ?
C8 C13 C12 C17 177.7(5) . . . . ?
C8 C7 C5 O5 -177.0(6) . . . . ?
C8 C7 C5 C4 2.7(11) . . . . ?
C19 O3 C15 C14 10.6(10) . . . . ?
C19 O3 C15 C16 -168.6(6) . . . . ?
C12 C13 C8 C7 178.7(6) . . . . ?
C12 C13 C8 C9 -0.3(9) . . . . ?
C12 C17 C16 O2 179.5(6) . . . . ?
C12 C17 C16 C15 0.5(9) . . . . ?
C16 C17 C12 C11 -178.8(6) . . . . ?
C16 C17 C12 C13 1.8(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.111
_oxdiff_exptl_absorpt_empirical_full_min 0.934
####################################################################### 
# 
# 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_20190328_czf_lls_l3_znaaa
_database_code_depnum_ccdc_archive 'CCDC 1946863'
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-04-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C42 H32 F6 N4 O16 Zn'
_chemical_formula_sum            'C42 H32 F6 N4 O16 Zn'
_chemical_formula_weight         1028.11
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2840 1.4300 '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'

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

_cell_length_a                   7.7839(4)
_cell_length_b                   11.4188(6)
_cell_length_c                   11.9926(6)
_cell_angle_alpha                73.088(5)
_cell_angle_beta                 86.180(4)
_cell_angle_gamma                77.830(5)
_cell_volume                     996.90(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2580
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.0450
_cell_measurement_theta_min      4.0930
_exptl_absorpt_coefficient_mu    0.729
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             524
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12086
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  88.00   1.00   15.00    --   17.61  77.00 -30.00  100
  2  ω    -18.00  32.00   1.00   15.00    --   17.61  89.00-166.00   50
  3  ω    -51.00  38.00   1.00   15.00    --   17.61 -57.00-150.00   89
  4  ω    -50.00  50.00   1.00   15.00    --  -19.88  77.00  90.00  100
  5  ω    -93.00  24.00   1.00   15.00    --  -19.88 -19.00 120.00  117
  6  ω    -89.00   2.00   1.00   15.00    --  -19.88 -57.00 -30.00   91
  7  ω     -4.00  27.00   1.00   15.00    --   17.61  57.00 120.00   31
  8  ω     34.00  94.00   1.00   15.00    --   17.61-178.00  60.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0587392000
_diffrn_orient_matrix_UB_12      0.0303861000
_diffrn_orient_matrix_UB_13      0.0354407000
_diffrn_orient_matrix_UB_21      -0.0014454000
_diffrn_orient_matrix_UB_22      -0.0585479000
_diffrn_orient_matrix_UB_23      0.0414288000
_diffrn_orient_matrix_UB_31      0.0723721000
_diffrn_orient_matrix_UB_32      0.0063756000
_diffrn_orient_matrix_UB_33      0.0291411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2876
_reflns_number_total             4072
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0860
_refine_ls_R_factor_gt           0.0569
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0625P)²+0.1737P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1505
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C17(H17), C12(H12), C4(H4), C2(H2), C21(H21)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C14(H14A,H14B,H14C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_site_symmetry_order
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Zn1 Zn 0.5000 -0.5000 0.5000 0.0425(2) Uani 1 d . . 2 S T P
F2 F 0.2859(5) 0.5000(2) 0.0459(3) 0.1047(11) Uani 1 d . . 1 . . .
F1 F 0.3723(5) 0.3900(3) -0.0719(2) 0.1030(11) Uani 1 d . . 1 . . .
O4 O 0.3146(3) 0.1760(2) 0.1097(2) 0.0427(6) Uani 1 d . . 1 . . .
O2 O -0.2912(3) -0.0361(2) 0.4492(2) 0.0428(6) Uani 1 d . . 1 . . .
O1 O 0.2850(3) -0.3470(2) 0.4875(2) 0.0382(6) Uani 1 d . . 1 . . .
O3 O -0.2299(3) 0.1679(2) 0.3068(2) 0.0448(6) Uani 1 d . . 1 . . .
O5 O 0.6266(3) 0.1627(2) 0.0180(2) 0.0526(7) Uani 1 d . . 1 . . .
O6 O 0.3817(3) -0.5662(2) 0.3730(2) 0.0543(7) Uani 1 d . . 1 . . .
O7 O 0.1276(4) -0.5692(3) 0.3178(3) 0.0817(10) Uani 1 d . . 1 . . .
O8 O 0.2183(4) -0.3981(3) 0.2696(3) 0.0730(9) Uani 1 d . . 1 . . .
N1 N 0.5890(3) -0.3639(2) 0.3739(2) 0.0351(7) Uani 1 d . . 1 . . .
C19 C 0.3062(4) -0.2550(3) 0.4074(3) 0.0306(7) Uani 1 d . . 1 . . .
C11 C 0.2058(4) -0.0335(3) 0.2901(3) 0.0285(7) Uani 1 d . . 1 . . .
C10 C 0.3799(4) -0.0337(3) 0.2327(3) 0.0296(7) Uani 1 d . . 1 . . .
C5 C 0.6035(5) 0.0564(3) 0.0989(3) 0.0388(8) Uani 1 d . . 1 . . .
C18 C 0.1714(4) -0.1420(3) 0.3738(3) 0.0288(7) Uani 1 d . . 1 . . .
C20 C 0.4750(4) -0.2553(3) 0.3435(3) 0.0303(7) Uani 1 d . . 1 . . .
C17 C 0.0060(4) -0.1455(3) 0.4269(3) 0.0318(7) Uani 1 d . . 1 . . .
H17 H -0.0137 -0.2192 0.4798 0.038 Uiso 1 calc . . 1 R . .
C24 C 0.5094(4) -0.1485(3) 0.2617(3) 0.0297(7) Uani 1 d . . 1 . . .
C12 C 0.0671(4) 0.0717(3) 0.2675(3) 0.0325(7) Uani 1 d . . 1 . . .
H12 H 0.0847 0.1454 0.2136 0.039 Uiso 1 calc . . 1 R . .
C15 C -0.1271(4) -0.0425(3) 0.4022(3) 0.0325(7) Uani 1 d . . 1 . . .
C3 C 0.6788(4) -0.1571(3) 0.2097(3) 0.0352(8) Uani 1 d . . 1 . . .
C7 C 0.4313(4) 0.0660(3) 0.1512(3) 0.0339(8) Uani 1 d . . 1 . . .
C4 C 0.7240(5) -0.0515(3) 0.1274(3) 0.0422(9) Uani 1 d . . 1 . . .
H4 H 0.8352 -0.0561 0.0932 0.051 Uiso 1 calc . . 1 R . .
N2 N 0.2411(4) -0.5109(3) 0.3210(3) 0.0455(8) Uani 1 d . . 1 . . .
C13 C -0.0936(4) 0.0691(3) 0.3228(3) 0.0331(8) Uani 1 d . . 1 . . .
C8 C 0.3518(5) 0.2873(3) 0.1274(3) 0.0490(10) Uani 1 d . . 1 . . .
H8A H 0.4775 0.2797 0.1338 0.059 Uiso 1 calc . . 1 R . .
H8B H 0.2958 0.3012 0.1985 0.059 Uiso 1 calc . . 1 R . .
C16 C -0.3271(4) -0.1468(3) 0.5314(3) 0.0424(9) Uani 1 d . . 1 . . .
H16A H -0.3072 -0.2135 0.4955 0.064 Uiso 1 calc . . 1 GR . .
H16B H -0.4473 -0.1320 0.5568 0.064 Uiso 1 calc . . 1 GR . .
H16C H -0.2509 -0.1695 0.5973 0.064 Uiso 1 calc . . 1 GR . .
C2 C 0.7982(4) -0.2712(3) 0.2436(3) 0.0413(9) Uani 1 d . . 1 . . .
H2 H 0.9108 -0.2790 0.2116 0.050 Uiso 1 calc . . 1 R . .
C14 C -0.1977(5) 0.2894(3) 0.2481(3) 0.0473(9) Uani 1 d . . 1 . . .
H14A H -0.1713 0.2952 0.1676 0.071 Uiso 1 calc . . 1 GR . .
H14B H -0.1000 0.3036 0.2836 0.071 Uiso 1 calc . . 1 GR . .
H14C H -0.3002 0.3512 0.2536 0.071 Uiso 1 calc . . 1 GR . .
C6 C 0.7957(5) 0.1657(4) -0.0351(3) 0.0514(10) Uani 1 d . . 1 . . .
H6A H 0.7968 0.2479 -0.0857 0.077 Uiso 1 calc . . 1 GR . .
H6B H 0.8212 0.1064 -0.0795 0.077 Uiso 1 calc . . 1 GR . .
H6C H 0.8829 0.1447 0.0243 0.077 Uiso 1 calc . . 1 GR . .
F3 F 0.1198(5) 0.3930(3) 0.0020(4) 0.1308(15) Uani 1 d . . 1 . . .
C9 C 0.2820(7) 0.3917(4) 0.0258(5) 0.0701(13) Uani 1 d . . 1 . . .
C21 C 0.7490(4) -0.3713(3) 0.3239(3) 0.0422(9) Uani 1 d . . 1 . . .
H21 H 0.8292 -0.4469 0.3445 0.051 Uiso 1 calc . . 1 R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 O1 2.127(2) . ?
Zn1 O1 2.127(2) 2_646 ?
Zn1 O6 2.211(3) . ?
Zn1 O6 2.211(3) 2_646 ?
Zn1 N1 2.032(3) 2_646 ?
Zn1 N1 2.032(3) . ?
F2 C9 1.334(5) . ?
F1 C9 1.329(6) . ?
O4 C7 1.365(4) . ?
O4 C8 1.438(4) . ?
O2 C15 1.358(4) . ?
O2 C16 1.427(4) . ?
O1 C19 1.232(4) . ?
O3 C13 1.353(4) . ?
O3 C14 1.428(4) . ?
O5 C5 1.353(4) . ?
O5 C6 1.426(4) . ?
O6 N2 1.248(4) . ?
O7 N2 1.222(4) . ?
O8 N2 1.236(4) . ?
N1 C20 1.332(4) . ?
N1 C21 1.343(4) . ?
C19 C18 1.453(4) . ?
C19 C20 1.476(5) . ?
C11 C10 1.478(4) . ?
C11 C18 1.412(4) . ?
C11 C12 1.409(4) . ?
C10 C24 1.442(4) . ?
C10 C7 1.380(4) . ?
C5 C7 1.437(5) . ?
C5 C4 1.351(5) . ?
C18 C17 1.401(4) . ?
C20 C24 1.388(4) . ?
C17 H17 0.9300 . ?
C17 C15 1.368(4) . ?
C24 C3 1.417(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.378(4) . ?
C15 C13 1.414(4) . ?
C3 C4 1.412(5) . ?
C3 C2 1.400(4) . ?
C4 H4 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.474(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C2 H2 0.9300 . ?
C2 C21 1.369(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
F3 C9 1.309(6) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Zn1 O1 180.0 2_646 . ?
O1 Zn1 O6 92.29(9) . . ?
O1 Zn1 O6 92.29(9) 2_646 2_646 ?
O1 Zn1 O6 87.71(9) . 2_646 ?
O1 Zn1 O6 87.71(9) 2_646 . ?
O6 Zn1 O6 180.0 2_646 . ?
N1 Zn1 O1 100.87(9) . 2_646 ?
N1 Zn1 O1 79.13(9) . . ?
N1 Zn1 O1 100.87(9) 2_646 . ?
N1 Zn1 O1 79.13(9) 2_646 2_646 ?
N1 Zn1 O6 86.76(11) 2_646 . ?
N1 Zn1 O6 93.24(11) . . ?
N1 Zn1 O6 93.24(11) 2_646 2_646 ?
N1 Zn1 O6 86.76(11) . 2_646 ?
N1 Zn1 N1 180.0 . 2_646 ?
C7 O4 C8 118.3(3) . . ?
C15 O2 C16 116.9(3) . . ?
C19 O1 Zn1 111.6(2) . . ?
C13 O3 C14 118.5(3) . . ?
C5 O5 C6 118.1(3) . . ?
N2 O6 Zn1 123.9(2) . . ?
C20 N1 Zn1 114.4(2) . . ?
C20 N1 C21 118.4(3) . . ?
C21 N1 Zn1 127.1(2) . . ?
O1 C19 C18 122.5(3) . . ?
O1 C19 C20 120.2(3) . . ?
C18 C19 C20 117.3(3) . . ?
C18 C11 C10 120.4(3) . . ?
C12 C11 C10 123.5(3) . . ?
C12 C11 C18 116.1(3) . . ?
C24 C10 C11 118.0(3) . . ?
C7 C10 C11 126.2(3) . . ?
C7 C10 C24 115.8(3) . . ?
O5 C5 C7 113.3(3) . . ?
C4 C5 O5 125.1(3) . . ?
C4 C5 C7 121.5(3) . . ?
C11 C18 C19 121.2(3) . . ?
C17 C18 C19 117.3(3) . . ?
C17 C18 C11 121.5(3) . . ?
N1 C20 C19 114.3(3) . . ?
N1 C20 C24 124.3(3) . . ?
C24 C20 C19 121.3(3) . . ?
C18 C17 H17 119.5 . . ?
C15 C17 C18 121.1(3) . . ?
C15 C17 H17 119.5 . . ?
C20 C24 C10 121.5(3) . . ?
C20 C24 C3 116.8(3) . . ?
C3 C24 C10 121.6(3) . . ?
C11 C12 H12 118.9 . . ?
C13 C12 C11 122.2(3) . . ?
C13 C12 H12 118.9 . . ?
O2 C15 C17 125.6(3) . . ?
O2 C15 C13 115.8(3) . . ?
C17 C15 C13 118.5(3) . . ?
C4 C3 C24 119.9(3) . . ?
C2 C3 C24 118.3(3) . . ?
C2 C3 C4 121.8(3) . . ?
O4 C7 C10 120.8(3) . . ?
O4 C7 C5 116.9(3) . . ?
C10 C7 C5 122.1(3) . . ?
C5 C4 C3 119.0(3) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O7 N2 O6 119.8(3) . . ?
O7 N2 O8 119.9(3) . . ?
O8 N2 O6 120.3(3) . . ?
O3 C13 C12 124.8(3) . . ?
O3 C13 C15 114.7(3) . . ?
C12 C13 C15 120.5(3) . . ?
O4 C8 H8A 110.3 . . ?
O4 C8 H8B 110.3 . . ?
O4 C8 C9 106.9(3) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.3 . . ?
C9 C8 H8B 110.3 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C2 H2 120.1 . . ?
C21 C2 C3 119.9(3) . . ?
C21 C2 H2 120.1 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O5 C6 H6A 109.5 . . ?
O5 C6 H6B 109.5 . . ?
O5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
F2 C9 C8 109.7(4) . . ?
F1 C9 F2 106.9(4) . . ?
F1 C9 C8 113.7(4) . . ?
F3 C9 F2 108.0(4) . . ?
F3 C9 F1 105.5(5) . . ?
F3 C9 C8 112.6(4) . . ?
N1 C21 C2 122.2(3) . . ?
N1 C21 H21 118.9 . . ?
C2 C21 H21 118.9 . . ?

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
Zn1 O1 C19 C18 174.4(2) . . . . ?
Zn1 O1 C19 C20 -7.4(4) . . . . ?
Zn1 O6 N2 O7 -131.6(3) . . . . ?
Zn1 O6 N2 O8 50.8(5) . . . . ?
Zn1 N1 C20 C19 -0.1(3) . . . . ?
Zn1 N1 C20 C24 178.1(2) . . . . ?
Zn1 N1 C21 C2 -176.5(3) . . . . ?
O4 C8 C9 F2 169.7(4) . . . . ?
O4 C8 C9 F1 -70.7(5) . . . . ?
O4 C8 C9 F3 49.3(5) . . . . ?
O2 C15 C13 O3 1.4(4) . . . . ?
O2 C15 C13 C12 -178.1(3) . . . . ?
O1 Zn1 O1 C19 -132(100) 2_646 . . . ?
O1 Zn1 O6 N2 -176.9(3) 2_646 . . . ?
O1 Zn1 O6 N2 3.1(3) . . . . ?
O1 Zn1 N1 C20 177.3(2) 2_646 . . . ?
O1 Zn1 N1 C20 -2.7(2) . . . . ?
O1 Zn1 N1 C21 174.1(3) . . . . ?
O1 Zn1 N1 C21 -5.9(3) 2_646 . . . ?
O1 C19 C18 C11 173.2(3) . . . . ?
O1 C19 C18 C17 -7.4(5) . . . . ?
O1 C19 C20 N1 5.4(4) . . . . ?
O1 C19 C20 C24 -172.8(3) . . . . ?
O5 C5 C7 O4 2.9(5) . . . . ?
O5 C5 C7 C10 177.6(3) . . . . ?
O5 C5 C4 C3 -177.0(3) . . . . ?
O6 Zn1 O1 C19 92.7(2) 2_646 . . . ?
O6 Zn1 O1 C19 -87.3(2) . . . . ?
O6 Zn1 O6 N2 55(100) 2_646 . . . ?
O6 Zn1 N1 C20 -91.0(2) 2_646 . . . ?
O6 Zn1 N1 C20 89.0(2) . . . . ?
O6 Zn1 N1 C21 85.8(3) 2_646 . . . ?
O6 Zn1 N1 C21 -94.2(3) . . . . ?
N1 Zn1 O1 C19 -174.5(2) 2_646 . . . ?
N1 Zn1 O1 C19 5.5(2) . . . . ?
N1 Zn1 O6 N2 103.8(3) 2_646 . . . ?
N1 Zn1 O6 N2 -76.2(3) . . . . ?
N1 Zn1 N1 C20 93(100) 2_646 . . . ?
N1 Zn1 N1 C21 -90(100) 2_646 . . . ?
N1 C20 C24 C10 179.9(3) . . . . ?
N1 C20 C24 C3 -1.2(5) . . . . ?
C19 C18 C17 C15 178.5(3) . . . . ?
C19 C20 C24 C10 -2.0(5) . . . . ?
C19 C20 C24 C3 176.9(3) . . . . ?
C11 C10 C24 C20 -1.9(4) . . . . ?
C11 C10 C24 C3 179.3(3) . . . . ?
C11 C10 C7 O4 -4.6(5) . . . . ?
C11 C10 C7 C5 -179.2(3) . . . . ?
C11 C18 C17 C15 -2.1(5) . . . . ?
C11 C12 C13 O3 178.3(3) . . . . ?
C11 C12 C13 C15 -2.3(5) . . . . ?
C10 C11 C18 C19 1.3(4) . . . . ?
C10 C11 C18 C17 -178.0(3) . . . . ?
C10 C11 C12 C13 -179.8(3) . . . . ?
C10 C24 C3 C4 0.1(5) . . . . ?
C10 C24 C3 C2 179.1(3) . . . . ?
C18 C19 C20 N1 -176.3(3) . . . . ?
C18 C19 C20 C24 5.4(4) . . . . ?
C18 C11 C10 C24 2.2(4) . . . . ?
C18 C11 C10 C7 -178.9(3) . . . . ?
C18 C11 C12 C13 -0.7(5) . . . . ?
C18 C17 C15 O2 -179.6(3) . . . . ?
C18 C17 C15 C13 -0.9(5) . . . . ?
C20 N1 C21 C2 0.2(5) . . . . ?
C20 C19 C18 C11 -5.0(4) . . . . ?
C20 C19 C18 C17 174.3(3) . . . . ?
C20 C24 C3 C4 -178.8(3) . . . . ?
C20 C24 C3 C2 0.2(5) . . . . ?
C17 C15 C13 O3 -177.5(3) . . . . ?
C17 C15 C13 C12 3.1(5) . . . . ?
C24 C10 C7 O4 174.3(3) . . . . ?
C24 C10 C7 C5 -0.3(5) . . . . ?
C24 C3 C4 C5 -0.4(5) . . . . ?
C24 C3 C2 C21 0.9(5) . . . . ?
C12 C11 C10 C24 -178.7(3) . . . . ?
C12 C11 C10 C7 0.2(5) . . . . ?
C12 C11 C18 C19 -177.8(3) . . . . ?
C12 C11 C18 C17 2.8(4) . . . . ?
C3 C2 C21 N1 -1.1(5) . . . . ?
C7 O4 C8 C9 147.0(3) . . . . ?
C7 C10 C24 C20 179.1(3) . . . . ?
C7 C10 C24 C3 0.3(5) . . . . ?
C7 C5 C4 C3 0.5(5) . . . . ?
C4 C5 C7 O4 -174.8(3) . . . . ?
C4 C5 C7 C10 -0.1(5) . . . . ?
C4 C3 C2 C21 179.9(3) . . . . ?
C8 O4 C7 C10 119.9(3) . . . . ?
C8 O4 C7 C5 -65.3(4) . . . . ?
C16 O2 C15 C17 0.0(5) . . . . ?
C16 O2 C15 C13 -178.8(3) . . . . ?
C2 C3 C4 C5 -179.4(3) . . . . ?
C14 O3 C13 C12 -13.5(5) . . . . ?
C14 O3 C13 C15 167.1(3) . . . . ?
C6 O5 C5 C7 176.8(3) . . . . ?
C6 O5 C5 C4 -5.6(5) . . . . ?
C21 N1 C20 C19 -177.2(3) . . . . ?
C21 N1 C20 C24 1.0(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.649
_oxdiff_exptl_absorpt_empirical_full_min 0.697
####################################################################### 
# 
# 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_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1946864'
_audit_update_record             
;
2019-08-13 deposited with the CCDC.	2021-02-04 downloaded from the CCDC.
;
_audit_creation_date             2019-03-26
_audit_creation_method           
;
  Olex2 1.2
  (compiled 2012.05.09 svn.r2324, GUI svn.r4230)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 F3 N O5'
_chemical_formula_sum            'C21 H16 F3 N O5'
_chemical_formula_weight         419.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           88
_space_group_name_H-M_alt        'I 41/a'
_space_group_name_Hall           '-I 4ad'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y+3/4, x+1/4, z+1/4'
'-x, -y+1/2, z'
'y+1/4, -x+1/4, z+1/4'
'x+1/2, y+1/2, z+1/2'
'-y+5/4, x+3/4, z+3/4'
'-x+1/2, -y+1, z+1/2'
'y+3/4, -x+3/4, z+3/4'
'-x, -y, -z'
'y-3/4, -x-1/4, -z-1/4'
'x, y-1/2, -z'
'-y-1/4, x-1/4, -z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'y-1/4, -x+1/4, -z+1/4'
'x+1/2, y, -z+1/2'
'-y+1/4, x+1/4, -z+1/4'

_cell_length_a                   23.545(13)
_cell_length_b                   23.545(13)
_cell_length_c                   13.805(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7653(9)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    7569
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.36
_cell_measurement_theta_min      2.43
_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            RED
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3456
_exptl_crystal_size_max          0.410
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.120
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            29705
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.154
_diffrn_reflns_theta_min         1.710
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2458
_reflns_number_total             3820
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0517
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0739P)²+8.0245P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1345
_refine_ls_wR_factor_ref         0.1687
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.35303(10) 0.26163(8) 0.6809(2) 0.1231(9) Uani 1 1 d . . . . .
F2 F 0.41508(11) 0.24670(9) 0.7903(2) 0.1414(11) Uani 1 1 d . . . . .
F3 F 0.43991(12) 0.26060(9) 0.6417(2) 0.1407(11) Uani 1 1 d . . . . .
O1 O 0.50590(7) 0.38327(7) 0.62786(15) 0.0633(5) Uani 1 1 d . . . . .
O2 O 0.27591(8) 0.61722(7) 0.65041(15) 0.0641(5) Uani 1 1 d . . . . .
O3 O 0.13381(7) 0.45618(8) 0.65018(14) 0.0609(5) Uani 1 1 d . . . . .
O4 O 0.19332(7) 0.36253(7) 0.64396(14) 0.0588(5) Uani 1 1 d . . . . .
O5 O 0.39550(7) 0.36937(7) 0.64487(13) 0.0526(4) Uani 1 1 d . . . . .
N1 N 0.39044(10) 0.63041(9) 0.63972(19) 0.0670(7) Uani 1 1 d . . . . .
C1 C 0.56722(12) 0.38844(13) 0.6247(3) 0.0763(9) Uani 1 1 d . . . . .
H1A H 0.5779 0.4121 0.5711 0.114 Uiso 1 1 calc R U . . .
H1B H 0.5838 0.3515 0.6169 0.114 Uiso 1 1 calc R U . . .
H1C H 0.5805 0.4051 0.6839 0.114 Uiso 1 1 calc R U . . .
C2 C 0.47546(10) 0.43280(10) 0.63142(17) 0.0473(6) Uani 1 1 d . . . . .
C3 C 0.49862(10) 0.48585(10) 0.62677(18) 0.0511(6) Uani 1 1 d . . . . .
H3 H 0.5377 0.4903 0.6210 0.061 Uiso 1 1 calc R U . . .
C4 C 0.46259(10) 0.53413(10) 0.63086(17) 0.0480(6) Uani 1 1 d . . . . .
C5 C 0.48439(12) 0.58997(11) 0.6290(2) 0.0669(8) Uani 1 1 d . . . . .
H5 H 0.5233 0.5961 0.6241 0.080 Uiso 1 1 calc R U . . .
C6 C 0.44770(13) 0.63534(12) 0.6343(3) 0.0819(10) Uani 1 1 d . . . . .
H6 H 0.4632 0.6717 0.6341 0.098 Uiso 1 1 calc R U . . .
C7 C 0.36895(10) 0.57760(9) 0.64117(17) 0.0453(5) Uani 1 1 d . . . . .
C8 C 0.40202(9) 0.52738(9) 0.63719(15) 0.0406(5) Uani 1 1 d . . . . .
C9 C 0.30558(10) 0.57383(10) 0.64757(16) 0.0427(5) Uani 1 1 d . . . . .
C10 C 0.28043(9) 0.51629(9) 0.64875(14) 0.0371(5) Uani 1 1 d . . . . .
C11 C 0.22049(9) 0.51367(10) 0.65111(15) 0.0435(5) Uani 1 1 d . . . . .
H11 H 0.1997 0.5472 0.6540 0.052 Uiso 1 1 calc R U . . .
C12 C 0.10125(11) 0.50763(14) 0.6560(2) 0.0693(8) Uani 1 1 d . . . . .
H12A H 0.1102 0.5315 0.6017 0.104 Uiso 1 1 calc R U . . .
H12B H 0.1103 0.5272 0.7150 0.104 Uiso 1 1 calc R U . . .
H12C H 0.0615 0.4986 0.6550 0.104 Uiso 1 1 calc R U . . .
C13 C 0.19218(9) 0.46262(10) 0.64918(16) 0.0441(5) Uani 1 1 d . . . . .
C14 C 0.22448(9) 0.41197(10) 0.64546(16) 0.0431(5) Uani 1 1 d . . . . .
C15 C 0.22326(12) 0.30977(11) 0.6381(2) 0.0621(7) Uani 1 1 d . . . . .
H15A H 0.2465 0.3095 0.5810 0.093 Uiso 1 1 calc R U . . .
H15B H 0.1965 0.2791 0.6351 0.093 Uiso 1 1 calc R U . . .
H15C H 0.2469 0.3054 0.6943 0.093 Uiso 1 1 calc R U . . .
C16 C 0.28367(9) 0.41388(10) 0.64332(15) 0.0403(5) Uani 1 1 d . . . . .
H16 H 0.3041 0.3801 0.6407 0.048 Uiso 1 1 calc R U . . .
C17 C 0.31345(9) 0.46640(9) 0.64510(14) 0.0356(5) Uani 1 1 d . . . . .
C18 C 0.37703(9) 0.47079(9) 0.64121(15) 0.0368(5) Uani 1 1 d . . . . .
C19 C 0.41452(9) 0.42538(9) 0.64070(16) 0.0426(5) Uani 1 1 d . . . . .
C20 C 0.40863(13) 0.33952(11) 0.7326(2) 0.0656(8) Uani 1 1 d . . . . .
H20A H 0.3822 0.3501 0.7834 0.079 Uiso 1 1 calc R U . . .
H20B H 0.4468 0.3488 0.7540 0.079 Uiso 1 1 calc R U . . .
C21 C 0.40409(15) 0.27754(13) 0.7116(3) 0.0866(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C21 1.328(4) . ?
F2 C21 1.333(4) . ?
F3 C21 1.342(4) . ?
O1 C1 1.450(3) . ?
O1 C2 1.370(3) . ?
O2 C9 1.238(3) . ?
O3 C12 1.436(3) . ?
O3 C13 1.383(3) . ?
O4 C14 1.376(3) . ?
O4 C15 1.431(3) . ?
O5 C19 1.394(3) . ?
O5 C20 1.434(3) . ?
N1 C6 1.355(4) . ?
N1 C7 1.343(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.365(3) . ?
C2 C19 1.451(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.420(3) . ?
C4 C5 1.412(3) . ?
C4 C8 1.438(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.376(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.417(3) . ?
C7 C9 1.497(3) . ?
C8 C18 1.458(3) . ?
C9 C10 1.479(3) . ?
C10 C11 1.413(3) . ?
C10 C17 1.410(3) . ?
C11 H11 0.9300 . ?
C11 C13 1.375(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.415(3) . ?
C14 C16 1.395(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.422(3) . ?
C17 C18 1.502(3) . ?
C18 C19 1.386(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.492(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
C2 O1 C1 116.8(2) . . ?
C13 O3 C12 116.0(2) . . ?
C14 O4 C15 118.21(19) . . ?
C19 O5 C20 115.41(19) . . ?
C7 N1 C6 117.1(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C19 114.7(2) . . ?
C3 C2 O1 124.6(2) . . ?
C3 C2 C19 120.6(2) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.5(2) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C8 120.5(2) . . ?
C5 C4 C3 121.9(2) . . ?
C5 C4 C8 117.7(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.6(3) . . ?
C6 C5 H5 120.2 . . ?
N1 C6 C5 124.1(3) . . ?
N1 C6 H6 117.9 . . ?
C5 C6 H6 117.9 . . ?
N1 C7 C8 124.4(2) . . ?
N1 C7 C9 115.5(2) . . ?
C8 C7 C9 120.0(2) . . ?
C4 C8 C18 120.2(2) . . ?
C7 C8 C4 117.1(2) . . ?
C7 C8 C18 122.7(2) . . ?
O2 C9 C7 121.0(2) . . ?
O2 C9 C10 122.0(2) . . ?
C10 C9 C7 117.00(19) . . ?
C11 C10 C9 116.1(2) . . ?
C17 C10 C9 122.85(19) . . ?
C17 C10 C11 121.0(2) . . ?
C10 C11 H11 119.3 . . ?
C13 C11 C10 121.5(2) . . ?
C13 C11 H11 119.3 . . ?
O3 C12 H12A 109.5 . . ?
O3 C12 H12B 109.5 . . ?
O3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 C14 116.2(2) . . ?
C11 C13 O3 125.3(2) . . ?
C11 C13 C14 118.5(2) . . ?
O4 C14 C13 115.27(19) . . ?
O4 C14 C16 124.0(2) . . ?
C16 C14 C13 120.7(2) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16 119.3 . . ?
C14 C16 C17 121.4(2) . . ?
C17 C16 H16 119.3 . . ?
C10 C17 C16 116.97(19) . . ?
C10 C17 C18 119.58(18) . . ?
C16 C17 C18 123.44(19) . . ?
C8 C18 C17 117.82(18) . . ?
C19 C18 C8 116.60(19) . . ?
C19 C18 C17 125.57(19) . . ?
O5 C19 C2 115.80(19) . . ?
C18 C19 O5 121.65(19) . . ?
C18 C19 C2 122.5(2) . . ?
O5 C20 H20A 110.2 . . ?
O5 C20 H20B 110.2 . . ?
O5 C20 C21 107.4(3) . . ?
H20A C20 H20B 108.5 . . ?
C21 C20 H20A 110.2 . . ?
C21 C20 H20B 110.2 . . ?
F1 C21 F2 106.4(3) . . ?
F1 C21 F3 104.8(4) . . ?
F1 C21 C20 113.8(3) . . ?
F2 C21 F3 107.6(3) . . ?
F2 C21 C20 111.1(3) . . ?
F3 C21 C20 112.7(3) . . ?

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
C3 H3 O2 0.93 2.41 3.318(3) 166.0 16_656
C5 H5 N1 0.93 2.50 3.407(4) 164.2 16_656
C12 H12B O2 0.96 2.61 3.482(4) 150.6 2
C16 H16 O5 0.93 2.17 2.834(3) 127.7 .
C20 H20B O1 0.97 2.37 2.898(4) 113.4 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 179.8(2) . . . . ?
O1 C2 C19 O5 0.1(3) . . . . ?
O1 C2 C19 C18 -177.2(2) . . . . ?
O2 C9 C10 C11 1.4(3) . . . . ?
O2 C9 C10 C17 179.7(2) . . . . ?
O3 C13 C14 O4 -0.4(3) . . . . ?
O3 C13 C14 C16 179.44(19) . . . . ?
O4 C14 C16 C17 -180.0(2) . . . . ?
O5 C20 C21 F1 -59.2(4) . . . . ?
O5 C20 C21 F2 -179.3(3) . . . . ?
O5 C20 C21 F3 59.9(4) . . . . ?
N1 C7 C8 C4 -0.2(4) . . . . ?
N1 C7 C8 C18 178.5(2) . . . . ?
N1 C7 C9 O2 0.6(3) . . . . ?
N1 C7 C9 C10 179.7(2) . . . . ?
C1 O1 C2 C3 3.8(4) . . . . ?
C1 O1 C2 C19 -176.3(2) . . . . ?
C2 C3 C4 C5 178.3(3) . . . . ?
C2 C3 C4 C8 -1.7(4) . . . . ?
C3 C2 C19 O5 -180.0(2) . . . . ?
C3 C2 C19 C18 2.8(4) . . . . ?
C3 C4 C5 C6 -179.2(3) . . . . ?
C3 C4 C8 C7 179.9(2) . . . . ?
C3 C4 C8 C18 1.1(3) . . . . ?
C4 C5 C6 N1 -1.2(5) . . . . ?
C4 C8 C18 C17 -178.40(19) . . . . ?
C4 C8 C18 C19 1.4(3) . . . . ?
C5 C4 C8 C7 -0.1(3) . . . . ?
C5 C4 C8 C18 -178.9(2) . . . . ?
C6 N1 C7 C8 -0.2(4) . . . . ?
C6 N1 C7 C9 179.8(3) . . . . ?
C7 N1 C6 C5 0.9(5) . . . . ?
C7 C8 C18 C17 2.9(3) . . . . ?
C7 C8 C18 C19 -177.4(2) . . . . ?
C7 C9 C10 C11 -177.68(19) . . . . ?
C7 C9 C10 C17 0.6(3) . . . . ?
C8 C4 C5 C6 0.7(4) . . . . ?
C8 C7 C9 O2 -179.5(2) . . . . ?
C8 C7 C9 C10 -0.4(3) . . . . ?
C8 C18 C19 O5 179.63(19) . . . . ?
C8 C18 C19 C2 -3.2(3) . . . . ?
C9 C7 C8 C4 179.8(2) . . . . ?
C9 C7 C8 C18 -1.4(3) . . . . ?
C9 C10 C11 C13 177.84(19) . . . . ?
C9 C10 C17 C16 -177.86(19) . . . . ?
C9 C10 C17 C18 0.9(3) . . . . ?
C10 C11 C13 O3 -179.3(2) . . . . ?
C10 C11 C13 C14 0.5(3) . . . . ?
C10 C17 C18 C8 -2.6(3) . . . . ?
C10 C17 C18 C19 177.7(2) . . . . ?
C11 C10 C17 C16 0.4(3) . . . . ?
C11 C10 C17 C18 179.11(18) . . . . ?
C11 C13 C14 O4 179.84(19) . . . . ?
C11 C13 C14 C16 -0.3(3) . . . . ?
C12 O3 C13 C11 -1.5(3) . . . . ?
C12 O3 C13 C14 178.8(2) . . . . ?
C13 C14 C16 C17 0.2(3) . . . . ?
C14 C16 C17 C10 -0.2(3) . . . . ?
C14 C16 C17 C18 -178.92(19) . . . . ?
C15 O4 C14 C13 178.7(2) . . . . ?
C15 O4 C14 C16 -1.2(3) . . . . ?
C16 C17 C18 C8 176.08(19) . . . . ?
C16 C17 C18 C19 -3.6(3) . . . . ?
C17 C10 C11 C13 -0.5(3) . . . . ?
C17 C18 C19 O5 -0.6(3) . . . . ?
C17 C18 C19 C2 176.5(2) . . . . ?
C19 O5 C20 C21 -160.4(2) . . . . ?
C19 C2 C3 C4 -0.1(4) . . . . ?
C20 O5 C19 C2 70.9(3) . . . . ?
C20 O5 C19 C18 -111.8(2) . . . . ?

_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.951
_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.
;
_shelxl_version_number           2013-2
