# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1978260'
loop_
_audit_author_name
_audit_author_address
'Guilherme P. Guedes'
;Universidade Federal Fluminense
Brazil
;

_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H40 Cu F12 N4 O6'
_chemical_formula_sum            'C28 H40 Cu F12 N4 O6'
_chemical_formula_weight         820.19

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   12.0543(3)
_cell_length_b                   11.8676(3)
_cell_length_c                   12.4149(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.7940(10)
_cell_angle_gamma                90
_cell_volume                     1755.14(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9216
_cell_measurement_theta_min      3.60
_cell_measurement_theta_max      72.37
_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_F_000             842
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.881
_shelx_estimated_absorpt_T_min   0.734
_shelx_estimated_absorpt_T_max   0.864
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6723
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26297
_diffrn_reflns_av_unetI/netI     0.0347
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.602
_diffrn_reflns_theta_max         72.398
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             6949
_reflns_number_gt                6435
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.876
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.976

_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_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_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)+(0.0338P)²+0.4471P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2838 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.003(10)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6828
_refine_ls_number_parameters     460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0308
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0656
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Cu1 Cu 0.75848(3) 0.29400(3) 0.77630(3) 0.01030(10) Uani 1 1 d . . . . .
F7 F 1.07493(14) 0.32055(17) 0.63563(16) 0.0279(5) Uani 1 1 d . . . . .
O4 O 0.80662(16) 0.13436(17) 0.77875(17) 0.0143(4) Uani 1 1 d . . . . .
F4 F 1.00037(18) 0.00984(17) 0.85122(19) 0.0368(5) Uani 1 1 d . . . . .
F9 F 1.19936(13) 0.3047(2) 0.77860(16) 0.0294(4) Uani 1 1 d . . . . .
F6 F 0.85553(16) -0.09153(16) 0.79613(18) 0.0299(5) Uani 1 1 d . . . . .
F5 F 0.98307(17) -0.07121(17) 0.69492(18) 0.0313(5) Uani 1 1 d . . . . .
F8 F 1.11529(17) 0.46326(17) 0.73946(19) 0.0322(5) Uani 1 1 d . . . . .
F11 F 0.95131(19) 0.23224(19) 1.16602(16) 0.0351(5) Uani 1 1 d . . . . .
O5 O 0.91063(15) 0.34815(17) 0.75408(18) 0.0147(4) Uani 1 1 d . . . . .
O3 O 0.74404(15) 0.26869(16) 0.58521(17) 0.0153(4) Uani 1 1 d . . . . .
F10 F 1.09921(17) 0.1746(2) 1.10673(19) 0.0364(5) Uani 1 1 d . . . . .
O2 O 0.45082(17) -0.06968(18) 1.05912(18) 0.0185(4) Uani 1 1 d . . . . .
F12 F 0.9429(2) 0.08428(17) 1.06642(19) 0.0384(5) Uani 1 1 d . . . . .
O6 O 0.85379(15) 0.2900(2) 0.96182(16) 0.0180(4) Uani 1 1 d . . . . .
F2 F 0.7871(2) 0.31666(19) 0.39036(18) 0.0417(6) Uani 1 1 d . . . . .
F3 F 0.7990(2) 0.1403(2) 0.37052(18) 0.0405(5) Uani 1 1 d . . . . .
F1 F 0.94643(17) 0.2322(3) 0.43074(19) 0.0497(7) Uani 1 1 d . . . . .
O1 O 0.57278(18) 0.6844(2) 0.41670(18) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.59651(19) 0.2478(2) 0.7816(2) 0.0112(5) Uani 1 1 d . . . . .
H4A H 0.5642 0.3046 0.8151 0.013 Uiso 1 1 calc R U . . .
H4B H 0.5608 0.2450 0.7116 0.013 Uiso 1 1 calc R U . . .
N3 N 0.48452(19) 0.0030(2) 0.9937(2) 0.0129(5) Uani 1 1 d . . . . .
N2 N 0.72722(19) 0.4589(2) 0.8031(2) 0.0124(5) Uani 1 1 d . . . . .
H2A H 0.6762 0.4603 0.8501 0.015 Uiso 1 1 calc R U . . .
H2B H 0.7919 0.4881 0.8399 0.015 Uiso 1 1 calc R U . . .
N1 N 0.60908(19) 0.6236(2) 0.5001(2) 0.0138(5) Uani 1 1 d . . . . .
C16 C 0.4100(2) 0.0206(3) 0.8870(3) 0.0163(6) Uani 1 1 d . . . . .
C24 C 1.0999(2) 0.3522(3) 0.7393(3) 0.0184(6) Uani 1 1 d . . . . .
C7 C 0.7330(2) 0.6331(2) 0.5411(2) 0.0140(6) Uani 1 1 d . . . . .
C6 C 0.7687(2) 0.5480(2) 0.6330(2) 0.0130(6) Uani 1 1 d . . . . .
H6A H 0.7761 0.4727 0.6006 0.016 Uiso 1 1 calc R U . . .
H6B H 0.8433 0.5699 0.6722 0.016 Uiso 1 1 calc R U . . .
C25 C 1.0061(2) 0.3216(2) 0.8048(3) 0.0140(6) Uani 1 1 d . . . . .
C19 C 0.8391(3) 0.2268(3) 0.4360(3) 0.0197(6) Uani 1 1 d . . . . .
C23 C 0.9269(2) -0.0170(3) 0.7638(3) 0.0174(6) Uani 1 1 d . . . . .
C20 C 0.8146(2) 0.2066(2) 0.5530(2) 0.0141(6) Uani 1 1 d . . . . .
C5 C 0.6866(2) 0.5402(2) 0.7145(2) 0.0126(6) Uani 1 1 d . . . . .
H5 H 0.6781 0.6163 0.7469 0.015 Uiso 1 1 calc R U . . .
C9 C 0.7938(3) 0.6050(3) 0.4454(3) 0.0210(7) Uani 1 1 d . . . . .
H9A H 0.8750 0.6102 0.4687 0.031 Uiso 1 1 calc R U . . .
H9B H 0.7743 0.5283 0.4200 0.031 Uiso 1 1 calc R U . . .
H9C H 0.7711 0.6585 0.3859 0.031 Uiso 1 1 calc R U . . .
C26 C 1.0345(2) 0.2749(2) 0.9067(3) 0.0165(6) Uani 1 1 d . . . . .
H26 H 1.1102 0.2538 0.9312 0.020 Uiso 1 1 calc R U . . .
C15 C 0.4442(2) 0.1299(3) 0.8351(2) 0.0141(6) Uani 1 1 d . . . . .
H15A H 0.4053 0.1337 0.7589 0.017 Uiso 1 1 calc R U . . .
H15B H 0.4185 0.1947 0.8750 0.017 Uiso 1 1 calc R U . . .
C14 C 0.5704(2) 0.1406(2) 0.8351(2) 0.0111(5) Uani 1 1 d . . . . .
H14 H 0.5972 0.0754 0.7951 0.013 Uiso 1 1 calc R U . . .
C28 C 0.9876(3) 0.1876(3) 1.0801(3) 0.0219(7) Uani 1 1 d . . . . .
C12 C 0.6748(3) -0.0681(3) 0.9806(3) 0.0205(7) Uani 1 1 d . . . . .
H12A H 0.7550 -0.0496 0.9939 0.031 Uiso 1 1 calc R U . . .
H12B H 0.6611 -0.1346 1.0235 0.031 Uiso 1 1 calc R U . . .
H12C H 0.6517 -0.0840 0.9030 0.031 Uiso 1 1 calc R U . . .
C27 C 0.9526(2) 0.2576(2) 0.9757(3) 0.0162(6) Uani 1 1 d . . . . .
C8 C 0.7591(3) 0.7541(3) 0.5792(3) 0.0205(7) Uani 1 1 d . . . . .
H8A H 0.8396 0.7612 0.6061 0.031 Uiso 1 1 calc R U . . .
H8B H 0.7382 0.8059 0.5181 0.031 Uiso 1 1 calc R U . . .
H8C H 0.7164 0.7725 0.6380 0.031 Uiso 1 1 calc R U . . .
C13 C 0.6286(2) 0.1393(2) 0.9527(2) 0.0133(6) Uani 1 1 d . . . . .
H13A H 0.6026 0.2048 0.9914 0.016 Uiso 1 1 calc R U . . .
H13B H 0.7105 0.1477 0.9536 0.016 Uiso 1 1 calc R U . . .
C21 C 0.8742(2) 0.1156(2) 0.6080(3) 0.0157(6) Uani 1 1 d . . . . .
H21 H 0.9234 0.0728 0.5711 0.019 Uiso 1 1 calc R U . . .
C1 C 0.5225(2) 0.5873(2) 0.5671(2) 0.0133(6) Uani 1 1 d . . . . .
C4 C 0.5740(2) 0.5022(2) 0.6536(2) 0.0134(6) Uani 1 1 d . . . . .
H4C H 0.5214 0.4904 0.7065 0.016 Uiso 1 1 calc R U . . .
H4D H 0.5837 0.4291 0.6178 0.016 Uiso 1 1 calc R U . . .
C10 C 0.6072(2) 0.0317(2) 1.0142(2) 0.0137(6) Uani 1 1 d . . . . .
C11 C 0.6391(3) 0.0540(3) 1.1361(3) 0.0202(7) Uani 1 1 d . . . . .
H11A H 0.7190 0.0730 1.1523 0.030 Uiso 1 1 calc R U . . .
H11B H 0.5944 0.1169 1.1574 0.030 Uiso 1 1 calc R U . . .
H11C H 0.6243 -0.0136 1.1770 0.030 Uiso 1 1 calc R U . . .
C17 C 0.4194(3) -0.0818(3) 0.8132(3) 0.0276(7) Uani 1 1 d . . . . .
H17A H 0.3708 -0.0707 0.7432 0.041 Uiso 1 1 calc R U . . .
H17B H 0.4974 -0.0901 0.8008 0.041 Uiso 1 1 calc R U . . .
H17C H 0.3962 -0.1499 0.8484 0.041 Uiso 1 1 calc R U . . .
C18 C 0.2890(2) 0.0304(3) 0.9094(3) 0.0276(8) Uani 1 1 d . . . . .
H18A H 0.2385 0.0420 0.8406 0.041 Uiso 1 1 calc R U . . .
H18B H 0.2679 -0.0389 0.9441 0.041 Uiso 1 1 calc R U . . .
H18C H 0.2830 0.0945 0.9580 0.041 Uiso 1 1 calc R U . . .
C22 C 0.8633(2) 0.0871(2) 0.7138(3) 0.0130(6) Uani 1 1 d . . . . .
C3 C 0.4776(2) 0.6917(3) 0.6183(3) 0.0185(6) Uani 1 1 d . . . . .
H3A H 0.4207 0.6691 0.6625 0.028 Uiso 1 1 calc R U . . .
H3B H 0.5394 0.7300 0.6645 0.028 Uiso 1 1 calc R U . . .
H3C H 0.4439 0.7430 0.5605 0.028 Uiso 1 1 calc R U . . .
C2 C 0.4280(2) 0.5293(3) 0.4899(3) 0.0203(7) Uani 1 1 d . . . . .
H2C H 0.3695 0.5042 0.5313 0.030 Uiso 1 1 calc R U . . .
H2D H 0.3958 0.5826 0.4333 0.030 Uiso 1 1 calc R U . . .
H2E H 0.4584 0.4641 0.4557 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.980(2) . ?
Cu1 O5 2.002(2) . ?
Cu1 N2 2.030(2) . ?
Cu1 N4 2.039(2) . ?
Cu1 O3 2.371(2) . ?
Cu1 O6 2.412(2) . ?
F7 C24 1.330(4) . ?
O4 C22 1.265(4) . ?
F4 C23 1.330(4) . ?
F9 C24 1.347(4) . ?
F6 C23 1.338(4) . ?
F5 C23 1.335(4) . ?
F8 C24 1.331(4) . ?
F11 C28 1.324(4) . ?
O5 C25 1.264(3) . ?
O3 C20 1.237(4) . ?
F10 C28 1.344(4) . ?
O2 N3 1.292(3) . ?
F12 C28 1.340(4) . ?
O6 C27 1.239(4) . ?
F2 C19 1.320(4) . ?
F3 C19 1.352(4) . ?
F1 C19 1.307(4) . ?
O1 N1 1.283(3) . ?
N4 C14 1.490(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N3 C16 1.498(4) . ?
N3 C10 1.501(3) . ?
N2 C5 1.489(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N1 C1 1.494(4) . ?
N1 C7 1.506(3) . ?
C16 C18 1.531(4) . ?
C16 C15 1.533(4) . ?
C16 C17 1.537(5) . ?
C24 C25 1.534(4) . ?
C7 C9 1.525(4) . ?
C7 C8 1.529(4) . ?
C7 C6 1.536(4) . ?
C6 C5 1.522(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C25 C26 1.376(4) . ?
C19 C20 1.546(4) . ?
C23 C22 1.534(4) . ?
C20 C21 1.413(4) . ?
C5 C4 1.518(4) . ?
C5 H5 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C26 C27 1.417(4) . ?
C26 H26 0.9500 . ?
C15 C14 1.527(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C14 C13 1.520(4) . ?
C14 H14 1.0000 . ?
C28 C27 1.544(4) . ?
C12 C10 1.531(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C13 C10 1.530(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C21 C22 1.382(4) . ?
C21 H21 0.9500 . ?
C1 C3 1.529(4) . ?
C1 C4 1.534(4) . ?
C1 C2 1.535(4) . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C10 C11 1.527(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O5 92.11(8) . . ?
O4 Cu1 N2 168.83(9) . . ?
O5 Cu1 N2 84.84(9) . . ?
O4 Cu1 N4 91.25(9) . . ?
O5 Cu1 N4 173.17(9) . . ?
N2 Cu1 N4 92.95(9) . . ?
O4 Cu1 O3 82.57(8) . . ?
O5 Cu1 O3 80.30(8) . . ?
N2 Cu1 O3 107.41(9) . . ?
N4 Cu1 O3 94.25(8) . . ?
O4 Cu1 O6 82.59(9) . . ?
O5 Cu1 O6 79.93(8) . . ?
N2 Cu1 O6 86.29(9) . . ?
N4 Cu1 O6 106.41(8) . . ?
O3 Cu1 O6 154.73(7) . . ?
C22 O4 Cu1 126.88(19) . . ?
C25 O5 Cu1 129.39(19) . . ?
C20 O3 Cu1 116.72(18) . . ?
C27 O6 Cu1 116.49(19) . . ?
C14 N4 Cu1 120.82(17) . . ?
C14 N4 H4A 107.1 . . ?
Cu1 N4 H4A 107.1 . . ?
C14 N4 H4B 107.1 . . ?
Cu1 N4 H4B 107.1 . . ?
H4A N4 H4B 106.8 . . ?
O2 N3 C16 116.4(2) . . ?
O2 N3 C10 116.2(2) . . ?
C16 N3 C10 124.1(2) . . ?
C5 N2 Cu1 123.49(19) . . ?
C5 N2 H2A 106.5 . . ?
Cu1 N2 H2A 106.5 . . ?
C5 N2 H2B 106.5 . . ?
Cu1 N2 H2B 106.5 . . ?
H2A N2 H2B 106.5 . . ?
O1 N1 C1 115.5(2) . . ?
O1 N1 C7 115.4(2) . . ?
C1 N1 C7 125.0(2) . . ?
N3 C16 C18 108.0(2) . . ?
N3 C16 C15 109.0(2) . . ?
C18 C16 C15 109.7(3) . . ?
N3 C16 C17 109.2(3) . . ?
C18 C16 C17 109.2(3) . . ?
C15 C16 C17 111.6(3) . . ?
F7 C24 F8 107.0(3) . . ?
F7 C24 F9 106.8(2) . . ?
F8 C24 F9 107.3(2) . . ?
F7 C24 C25 111.7(2) . . ?
F8 C24 C25 110.3(2) . . ?
F9 C24 C25 113.4(3) . . ?
N1 C7 C9 106.9(2) . . ?
N1 C7 C8 108.7(2) . . ?
C9 C7 C8 110.2(3) . . ?
N1 C7 C6 110.7(2) . . ?
C9 C7 C6 108.8(2) . . ?
C8 C7 C6 111.4(3) . . ?
C5 C6 C7 113.4(2) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
O5 C25 C26 129.7(3) . . ?
O5 C25 C24 111.4(3) . . ?
C26 C25 C24 118.9(2) . . ?
F1 C19 F2 110.4(3) . . ?
F1 C19 F3 105.8(3) . . ?
F2 C19 F3 104.7(3) . . ?
F1 C19 C20 112.8(3) . . ?
F2 C19 C20 112.5(3) . . ?
F3 C19 C20 110.2(3) . . ?
F4 C23 F5 107.4(2) . . ?
F4 C23 F6 107.0(3) . . ?
F5 C23 F6 106.6(2) . . ?
F4 C23 C22 111.5(2) . . ?
F5 C23 C22 113.6(3) . . ?
F6 C23 C22 110.4(2) . . ?
O3 C20 C21 128.5(3) . . ?
O3 C20 C19 116.8(3) . . ?
C21 C20 C19 114.6(3) . . ?
N2 C5 C4 110.1(2) . . ?
N2 C5 C6 110.9(2) . . ?
C4 C5 C6 108.0(2) . . ?
N2 C5 H5 109.3 . . ?
C4 C5 H5 109.3 . . ?
C6 C5 H5 109.3 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C25 C26 C27 121.0(2) . . ?
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C14 C15 C16 113.8(2) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
N4 C14 C13 109.9(2) . . ?
N4 C14 C15 110.4(2) . . ?
C13 C14 C15 108.2(2) . . ?
N4 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
F11 C28 F12 107.0(3) . . ?
F11 C28 F10 106.8(3) . . ?
F12 C28 F10 107.1(3) . . ?
F11 C28 C27 112.3(3) . . ?
F12 C28 C27 109.4(3) . . ?
F10 C28 C27 113.8(3) . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O6 C27 C26 128.0(3) . . ?
O6 C27 C28 114.7(3) . . ?
C26 C27 C28 117.3(3) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C13 C10 113.6(2) . . ?
C14 C13 H13A 108.9 . . ?
C10 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C10 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C22 C21 C20 122.1(3) . . ?
C22 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
N1 C1 C3 108.6(2) . . ?
N1 C1 C4 109.7(2) . . ?
C3 C1 C4 112.0(3) . . ?
N1 C1 C2 107.2(2) . . ?
C3 C1 C2 110.3(2) . . ?
C4 C1 C2 108.9(2) . . ?
C5 C4 C1 112.8(2) . . ?
C5 C4 H4C 109.0 . . ?
C1 C4 H4C 109.0 . . ?
C5 C4 H4D 109.0 . . ?
C1 C4 H4D 109.0 . . ?
H4C C4 H4D 107.8 . . ?
N3 C10 C11 107.4(2) . . ?
N3 C10 C13 110.0(2) . . ?
C11 C10 C13 108.3(2) . . ?
N3 C10 C12 109.3(2) . . ?
C11 C10 C12 109.9(2) . . ?
C13 C10 C12 111.8(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C22 C21 129.5(3) . . ?
O4 C22 C23 112.6(3) . . ?
C21 C22 C23 117.9(3) . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C1 C2 H2E 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 N3 C16 C18 45.1(3) . . . . ?
C10 N3 C16 C18 -156.1(3) . . . . ?
O2 N3 C16 C15 164.3(2) . . . . ?
C10 N3 C16 C15 -37.0(4) . . . . ?
O2 N3 C16 C17 -73.5(3) . . . . ?
C10 N3 C16 C17 85.2(3) . . . . ?
O1 N1 C7 C9 -55.9(3) . . . . ?
C1 N1 C7 C9 147.9(3) . . . . ?
O1 N1 C7 C8 63.1(3) . . . . ?
C1 N1 C7 C8 -93.2(3) . . . . ?
O1 N1 C7 C6 -174.2(2) . . . . ?
C1 N1 C7 C6 29.6(4) . . . . ?
N1 C7 C6 C5 -42.6(3) . . . . ?
C9 C7 C6 C5 -159.7(2) . . . . ?
C8 C7 C6 C5 78.5(3) . . . . ?
Cu1 O5 C25 C26 -20.6(4) . . . . ?
Cu1 O5 C25 C24 161.51(19) . . . . ?
F7 C24 C25 O5 -46.0(3) . . . . ?
F8 C24 C25 O5 72.9(3) . . . . ?
F9 C24 C25 O5 -166.7(2) . . . . ?
F7 C24 C25 C26 135.9(3) . . . . ?
F8 C24 C25 C26 -105.2(3) . . . . ?
F9 C24 C25 C26 15.1(4) . . . . ?
Cu1 O3 C20 C21 27.3(4) . . . . ?
Cu1 O3 C20 C19 -155.09(19) . . . . ?
F1 C19 C20 O3 131.6(3) . . . . ?
F2 C19 C20 O3 6.0(4) . . . . ?
F3 C19 C20 O3 -110.4(3) . . . . ?
F1 C19 C20 C21 -50.4(4) . . . . ?
F2 C19 C20 C21 -176.0(3) . . . . ?
F3 C19 C20 C21 67.6(3) . . . . ?
Cu1 N2 C5 C4 60.7(3) . . . . ?
Cu1 N2 C5 C6 -58.8(3) . . . . ?
C7 C6 C5 N2 -178.5(2) . . . . ?
C7 C6 C5 C4 60.8(3) . . . . ?
O5 C25 C26 C27 -5.4(5) . . . . ?
C24 C25 C26 C27 172.4(3) . . . . ?
N3 C16 C15 C14 47.6(3) . . . . ?
C18 C16 C15 C14 165.7(3) . . . . ?
C17 C16 C15 C14 -73.1(3) . . . . ?
Cu1 N4 C14 C13 56.7(3) . . . . ?
Cu1 N4 C14 C15 176.02(19) . . . . ?
C16 C15 C14 N4 179.0(2) . . . . ?
C16 C15 C14 C13 -60.7(3) . . . . ?
Cu1 O6 C27 C26 34.7(4) . . . . ?
Cu1 O6 C27 C28 -143.7(2) . . . . ?
C25 C26 C27 O6 -8.0(5) . . . . ?
C25 C26 C27 C28 170.4(3) . . . . ?
F11 C28 C27 O6 -44.4(4) . . . . ?
F12 C28 C27 O6 74.3(3) . . . . ?
F10 C28 C27 O6 -165.9(3) . . . . ?
F11 C28 C27 C26 137.0(3) . . . . ?
F12 C28 C27 C26 -104.3(3) . . . . ?
F10 C28 C27 C26 15.5(4) . . . . ?
N4 C14 C13 C10 -179.6(2) . . . . ?
C15 C14 C13 C10 59.7(3) . . . . ?
O3 C20 C21 C22 -3.2(5) . . . . ?
C19 C20 C21 C22 179.1(3) . . . . ?
O1 N1 C1 C3 -65.3(3) . . . . ?
C7 N1 C1 C3 90.9(3) . . . . ?
O1 N1 C1 C4 172.0(2) . . . . ?
C7 N1 C1 C4 -31.8(4) . . . . ?
O1 N1 C1 C2 53.8(3) . . . . ?
C7 N1 C1 C2 -149.9(3) . . . . ?
N2 C5 C4 C1 175.2(2) . . . . ?
C6 C5 C4 C1 -63.5(3) . . . . ?
N1 C1 C4 C5 47.5(3) . . . . ?
C3 C1 C4 C5 -73.2(3) . . . . ?
C2 C1 C4 C5 164.6(2) . . . . ?
O2 N3 C10 C11 -47.0(3) . . . . ?
C16 N3 C10 C11 154.2(3) . . . . ?
O2 N3 C10 C13 -164.7(2) . . . . ?
C16 N3 C10 C13 36.5(4) . . . . ?
O2 N3 C10 C12 72.2(3) . . . . ?
C16 N3 C10 C12 -86.6(3) . . . . ?
C14 C13 C10 N3 -46.3(3) . . . . ?
C14 C13 C10 C11 -163.4(2) . . . . ?
C14 C13 C10 C12 75.4(3) . . . . ?
Cu1 O4 C22 C21 -24.7(4) . . . . ?
Cu1 O4 C22 C23 155.67(18) . . . . ?
C20 C21 C22 O4 -2.9(5) . . . . ?
C20 C21 C22 C23 176.8(3) . . . . ?
F4 C23 C22 O4 -61.4(3) . . . . ?
F5 C23 C22 O4 177.0(2) . . . . ?
F6 C23 C22 O4 57.4(3) . . . . ?
F4 C23 C22 C21 118.8(3) . . . . ?
F5 C23 C22 C21 -2.7(4) . . . . ?
F6 C23 C22 C21 -122.3(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
N4 H4A O2 0.91 2.19 3.045(3) 156.8 2_657
N4 H4B O1 0.91 2.20 3.042(3) 152.7 2_646
N2 H2A O2 0.91 2.07 2.961(3) 167.5 2_657
C6 H6A O3 0.99 2.45 3.373(3) 154.1 .
C9 H9B F2 0.98 2.55 3.488(4) 161.0 .
C15 H15A O1 0.99 2.32 3.168(4) 143.7 2_646

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1978263'
loop_
_audit_author_name
_audit_author_address
'Guilherme P. Guedes'
;Universidade Federal Fluminense
Brazil
;
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: We tried several crystals, but they are of poor quality and diffract
 weakly.
;
_vrf_PLAT601_shelx               
;
PROBLEM: Structure Contains Solvent Accessible VOIDS of .        122 Ang**3
RESPONSE: It was not possible to assign intensities related to
 solvent molecules with the available data.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H21 Cu F12 N2 O5'
_chemical_formula_weight         648.92

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.826(2)
_cell_length_b                   21.226(2)
_cell_length_c                   12.0638(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.785(3)
_cell_angle_gamma                90
_cell_volume                     5255.3(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2793
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      17.11

_exptl_crystal_description       Block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             2608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.044
_exptl_absorpt_coefficient_mu    0.949
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.308
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11963
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.380
_diffrn_reflns_theta_max         23.253
_diffrn_reflns_theta_full        23.253
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3777
_reflns_number_gt                2837
_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_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_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)+(0.1362P)²+15.9715P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3777
_refine_ls_number_parameters     350
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0810
_refine_ls_wR_factor_ref         0.2403
_refine_ls_wR_factor_gt          0.2203
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.066
_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
Cu1 Cu 0.68471(3) 0.29006(3) 0.04840(6) 0.0370(4) Uani 1 1 d . . . . .
O2 O 0.7531(2) 0.23183(19) 0.1196(4) 0.0389(10) Uani 1 1 d . . . . .
O4 O 0.6296(2) 0.21882(18) -0.0123(4) 0.0457(12) Uani 1 1 d . . . . .
N2 N 0.7469(2) 0.3613(2) 0.0781(4) 0.0334(11) Uani 1 1 d . . . . .
H2A H 0.7860 0.3470 0.0699 0.040 Uiso 1 1 calc R U . . .
H2B H 0.7353 0.3899 0.0245 0.040 Uiso 1 1 calc R U . . .
O5 O 0.6146(2) 0.3496(2) -0.0027(5) 0.0618(15) Uani 1 1 d . . . . .
F1 F 0.8711(3) 0.2263(4) 0.2706(7) 0.147(3) Uani 1 1 d . . . . .
O1 O 0.7521(3) 0.5368(3) 0.4214(5) 0.0872(19) Uani 1 1 d . . . . .
F3 F 0.8314(4) 0.1559(4) 0.3633(5) 0.137(3) Uani 1 1 d . . . . .
C6 C 0.6905(3) 0.4204(3) 0.2076(7) 0.0562(19) Uani 1 1 d . . . . .
H6A H 0.6595 0.3860 0.2038 0.067 Uiso 1 1 calc R U . . .
H6B H 0.6745 0.4494 0.1471 0.067 Uiso 1 1 calc R U . . .
C1 C 0.8134(4) 0.4853(4) 0.3028(7) 0.063(2) Uani 1 1 d . . . . .
C5 C 0.7544(3) 0.3945(3) 0.1887(5) 0.0421(16) Uani 1 1 d . . . . .
H5 H 0.7703 0.3644 0.2488 0.051 Uiso 1 1 calc R U . . .
O3 O 0.6311(3) 0.2756(3) 0.1969(6) 0.0837(18) Uani 1 1 d . . . . .
F2 F 0.8389(4) 0.1421(4) 0.1941(6) 0.152(3) Uani 1 1 d . . . . .
N1 N 0.7503(3) 0.4972(3) 0.3400(5) 0.0570(16) Uani 1 1 d . . . . .
C2 C 0.8576(5) 0.4504(5) 0.3958(8) 0.109(4) Uani 1 1 d . . . . .
H2C H 0.8987 0.4424 0.3729 0.164 Uiso 1 1 calc R U . . .
H2D H 0.8642 0.4757 0.4628 0.164 Uiso 1 1 calc R U . . .
H2E H 0.8376 0.4112 0.4105 0.164 Uiso 1 1 calc R U . . .
C17 C 0.5298(3) 0.2746(3) -0.0517(6) 0.0513(18) Uani 1 1 d . . . . .
H17 H 0.4850 0.2700 -0.0734 0.062 Uiso 1 1 calc R U . . .
C16 C 0.5685(3) 0.2222(3) -0.0420(6) 0.0459(17) Uani 1 1 d . . . . .
C11 C 0.7597(4) 0.2157(3) 0.2224(6) 0.0445(17) Uani 1 1 d . . . . .
C3 C 0.8426(5) 0.5500(4) 0.2832(9) 0.092(3) Uani 1 1 d . . . . .
H3A H 0.8838 0.5444 0.2589 0.138 Uiso 1 1 calc R U . . .
H3B H 0.8135 0.5724 0.2265 0.138 Uiso 1 1 calc R U . . .
H3C H 0.8488 0.5737 0.3520 0.138 Uiso 1 1 calc R U . . .
C18 C 0.5559(3) 0.3350(3) -0.0297(6) 0.0520(18) Uani 1 1 d . . . . .
C12 C 0.7182(5) 0.2209(5) 0.2955(9) 0.094(3) Uani 1 1 d . U . . .
H12 H 0.7350 0.2074 0.3680 0.112 Uiso 1 1 calc R U . . .
C8 C 0.7004(9) 0.4045(6) 0.4174(10) 0.160(7) Uani 1 1 d . . . . .
H8A H 0.6640 0.3761 0.4061 0.240 Uiso 1 1 calc R U . . .
H8B H 0.7400 0.3811 0.4184 0.240 Uiso 1 1 calc R U . . .
H8C H 0.7021 0.4260 0.4878 0.240 Uiso 1 1 calc R U . . .
C7 C 0.6925(4) 0.4543(4) 0.3184(8) 0.076(3) Uani 1 1 d . . . . .
C10 C 0.8219(4) 0.1829(4) 0.2647(6) 0.062(2) Uani 1 1 d . . . . .
C4 C 0.8022(3) 0.4485(3) 0.1938(6) 0.0491(17) Uani 1 1 d . . . . .
H4A H 0.8437 0.4319 0.1811 0.059 Uiso 1 1 calc R U . . .
H4B H 0.7867 0.4774 0.1328 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6315(5) 0.4933(6) 0.3155(12) 0.138(6) Uani 1 1 d . . . . .
H9A H 0.5940 0.4664 0.3017 0.206 Uiso 1 1 calc R U . . .
H9B H 0.6330 0.5143 0.3864 0.206 Uiso 1 1 calc R U . . .
H9C H 0.6288 0.5241 0.2566 0.206 Uiso 1 1 calc R U . . .
C19 C 0.5096(4) 0.3911(4) -0.0409(10) 0.079(3) Uani 1 1 d . . . . .
F9 F 0.4744(2) 0.1629(2) -0.1101(7) 0.127(3) Uani 1 1 d . . . . .
F8 F 0.5642(3) 0.1243(4) -0.1261(10) 0.196(5) Uani 1 1 d . . . . .
F7 F 0.5383(4) 0.1279(3) 0.0312(10) 0.167(4) Uani 1 1 d . . . . .
C15 C 0.5355(4) 0.1606(4) -0.0683(12) 0.091(3) Uani 1 1 d . . . . .
F6 F 0.5783(5) 0.1808(4) 0.3502(8) 0.172(4) Uani 1 1 d . . . . .
C13 C 0.6557(5) 0.2425(4) 0.2820(8) 0.074(2) Uani 1 1 d . U . . .
F4 F 0.6419(4) 0.2296(4) 0.4750(5) 0.124(2) Uani 1 1 d . . . . .
F5 F 0.5645(5) 0.2812(4) 0.3468(13) 0.216(6) Uani 1 1 d . . . . .
C14 C 0.6089(7) 0.2340(6) 0.3654(12) 0.111(4) Uani 1 1 d . . . . .
F10A F 0.4543(8) 0.3782(7) -0.0167(13) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F11A F 0.5012(5) 0.4067(5) -0.1590(13) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F12A F 0.5366(6) 0.4407(6) 0.0071(14) 0.098(2) Uani 0.486(6) 1 d . . P A 1
F10B F 0.4472(7) 0.3789(7) -0.0735(12) 0.098(2) Uani 0.514(6) 1 d . . P A 2
F11B F 0.5251(5) 0.4397(6) -0.0838(13) 0.098(2) Uani 0.514(6) 1 d . . P A 2
F12B F 0.5067(5) 0.4126(5) 0.0745(12) 0.098(2) Uani 0.514(6) 1 d . . P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O5 1.950(4) . ?
Cu1 O4 1.964(4) . ?
Cu1 O2 1.970(4) . ?
Cu1 N2 1.983(5) . ?
Cu1 O3 2.287(7) . ?
O2 C11 1.272(8) . ?
O4 C16 1.263(8) . ?
N2 C5 1.494(7) . ?
O5 C18 1.248(8) . ?
F1 C10 1.371(10) . ?
O1 N1 1.288(7) . ?
F3 C10 1.305(9) . ?
C6 C5 1.493(9) . ?
C6 C7 1.512(10) . ?
C1 N1 1.481(10) . ?
C1 C4 1.513(10) . ?
C1 C2 1.516(11) . ?
C1 C3 1.537(11) . ?
C5 C4 1.513(9) . ?
O3 C13 1.277(11) . ?
F2 C10 1.305(9) . ?
N1 C7 1.496(10) . ?
C17 C16 1.367(9) . ?
C17 C18 1.401(10) . ?
C16 C15 1.486(11) . ?
C11 C12 1.339(12) . ?
C11 C10 1.483(10) . ?
C18 C19 1.524(10) . ?
C12 C13 1.364(13) . ?
C8 C7 1.583(15) . ?
C7 C9 1.513(13) . ?
C19 F11B 1.221(14) . ?
C19 F10A 1.265(18) . ?
C19 F12A 1.285(16) . ?
C19 F10B 1.319(17) . ?
C19 F11A 1.445(17) . ?
C19 F12B 1.476(16) . ?
F9 C15 1.287(9) . ?
F8 C15 1.255(12) . ?
F7 C15 1.379(14) . ?
F6 C14 1.294(13) . ?
C13 C14 1.527(13) . ?
F4 C14 1.386(15) . ?
F5 C14 1.354(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 Cu1 O4 91.24(19) . . ?
O5 Cu1 O2 172.6(2) . . ?
O4 Cu1 O2 90.76(18) . . ?
O5 Cu1 N2 89.67(19) . . ?
O4 Cu1 N2 167.7(2) . . ?
O2 Cu1 N2 89.89(18) . . ?
O5 Cu1 O3 84.0(2) . . ?
O4 Cu1 O3 81.7(2) . . ?
O2 Cu1 O3 89.3(2) . . ?
N2 Cu1 O3 110.6(2) . . ?
C11 O2 Cu1 123.0(4) . . ?
C16 O4 Cu1 124.0(4) . . ?
C5 N2 Cu1 119.2(4) . . ?
C18 O5 Cu1 124.7(4) . . ?
C5 C6 C7 114.7(6) . . ?
N1 C1 C4 109.7(6) . . ?
N1 C1 C2 108.5(8) . . ?
C4 C1 C2 112.1(6) . . ?
N1 C1 C3 106.8(6) . . ?
C4 C1 C3 109.5(7) . . ?
C2 C1 C3 110.1(8) . . ?
C6 C5 N2 110.5(5) . . ?
C6 C5 C4 108.2(5) . . ?
N2 C5 C4 111.2(5) . . ?
C13 O3 Cu1 121.4(6) . . ?
O1 N1 C1 115.4(6) . . ?
O1 N1 C7 116.7(6) . . ?
C1 N1 C7 124.9(5) . . ?
C16 C17 C18 121.5(6) . . ?
O4 C16 C17 128.5(6) . . ?
O4 C16 C15 114.6(6) . . ?
C17 C16 C15 116.9(6) . . ?
O2 C11 C12 130.2(8) . . ?
O2 C11 C10 113.9(6) . . ?
C12 C11 C10 115.9(7) . . ?
O5 C18 C17 127.5(6) . . ?
O5 C18 C19 113.9(6) . . ?
C17 C18 C19 118.6(7) . . ?
C11 C12 C13 131.2(10) . . ?
N1 C7 C6 110.2(6) . . ?
N1 C7 C9 108.5(7) . . ?
C6 C7 C9 110.0(8) . . ?
N1 C7 C8 107.4(9) . . ?
C6 C7 C8 109.5(7) . . ?
C9 C7 C8 111.3(10) . . ?
F3 C10 F2 106.8(7) . . ?
F3 C10 F1 104.6(7) . . ?
F2 C10 F1 101.4(8) . . ?
F3 C10 C11 120.4(7) . . ?
F2 C10 C11 113.9(6) . . ?
F1 C10 C11 107.6(7) . . ?
C1 C4 C5 115.4(6) . . ?
F10A C19 F12A 114.8(12) . . ?
F11B C19 F10B 110.9(10) . . ?
F10A C19 F11A 108.3(10) . . ?
F12A C19 F11A 103.1(10) . . ?
F11B C19 F12B 101.2(11) . . ?
F10B C19 F12B 98.4(10) . . ?
F11B C19 C18 119.3(8) . . ?
F10A C19 C18 113.4(10) . . ?
F12A C19 C18 112.3(8) . . ?
F10B C19 C18 116.8(10) . . ?
F11A C19 C18 103.7(9) . . ?
F12B C19 C18 106.6(8) . . ?
F8 C15 F9 109.7(9) . . ?
F8 C15 F7 102.8(9) . . ?
F9 C15 F7 104.6(9) . . ?
F8 C15 C16 114.4(9) . . ?
F9 C15 C16 116.2(7) . . ?
F7 C15 C16 107.9(9) . . ?
O3 C13 C12 121.7(9) . . ?
O3 C13 C14 112.4(10) . . ?
C12 C13 C14 125.8(11) . . ?
F6 C14 F5 108.5(12) . . ?
F6 C14 F4 103.3(10) . . ?
F5 C14 F4 115.0(12) . . ?
F6 C14 C13 111.3(10) . . ?
F5 C14 C13 107.3(10) . . ?
F4 C14 C13 111.5(11) . . ?

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
N2 H2A O4 0.89 2.44 3.293(6) 160.9 7_655
N2 H2B O1 0.89 2.06 2.887(7) 154.4 6_565
C6 H6A O5 0.97 2.62 3.136(9) 113.2 .
C6 H6A O3 0.97 2.41 3.307(9) 152.7 .
C4 H4A F8 0.97 2.44 3.402(9) 169.2 7_655
C4 H4B O1 0.97 2.55 3.289(9) 133.4 6_565
C9 H9B F11B 0.96 2.53 3.053(15) 114.2 6_566
C9 H9C F2 0.96 2.63 3.223(15) 119.9 4_655

_refine_diff_density_max         1.094
_refine_diff_density_min         -0.645
_refine_diff_density_rms         0.122

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1978262'
loop_
_audit_author_name
_audit_author_address
'Guilherme P. Guedes'
;Universidade Federal Fluminense
Brazil
;

_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H23 F24 N2 Nd O9, C9 H20 N2 O, H2 O'
_chemical_formula_sum            'C38 H45 F24 N4 Nd O11'
_chemical_formula_weight         1333.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0180 0.0090 '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'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0730 0.0530 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Nd Nd -3.1810 10.9080 '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                   16.6805(5)
_cell_length_b                   11.8287(4)
_cell_length_c                   27.8879(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.118(2)
_cell_angle_gamma                90
_cell_volume                     5312.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9274
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      72.25

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_F_000             2660
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    8.752
_shelx_estimated_absorpt_T_min   0.193
_shelx_estimated_absorpt_T_max   0.541
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3887
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            101936
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         72.438
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             10462
_reflns_number_gt                9189
_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_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_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)+(0.0542P)²+21.1565P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10532
_refine_ls_number_parameters     711
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Nd1 Nd 0.33508(2) 0.19012(2) 0.10812(2) 0.01904(8) Uani 1 1 d . . . . .
O2 O 0.35079(19) 0.3902(3) 0.13212(12) 0.0280(7) Uani 1 1 d . . . . .
N2 N 0.3972(2) 0.3073(3) 0.04558(14) 0.0273(8) Uani 1 1 d . . . . .
H2A H 0.4276 0.3639 0.0637 0.033 Uiso 1 1 calc R U . . .
H2B H 0.4341 0.2607 0.0365 0.033 Uiso 1 1 calc R U . . .
O5 O 0.26289(18) 0.1398(3) 0.01962(11) 0.0265(7) Uani 1 1 d . . . . .
F6 F 0.2124(3) 0.1911(3) 0.25713(14) 0.0580(10) Uani 1 1 d . . . . .
O3 O 0.2840(2) 0.2246(3) 0.18520(12) 0.0298(7) Uani 1 1 d . . . . .
O4 O 0.40961(18) 0.0426(3) 0.07514(12) 0.0298(7) Uani 1 1 d . . . . .
O8 O 0.39274(19) 0.0510(3) 0.17453(12) 0.0323(7) Uani 1 1 d . . . . .
O6 O 0.23385(18) 0.0406(3) 0.10271(12) 0.0285(7) Uani 1 1 d . . . . .
O9 O 0.48494(18) 0.2180(3) 0.14065(13) 0.0324(8) Uani 1 1 d . . . . .
O1 O 0.2485(2) 0.5799(3) -0.11597(12) 0.0319(7) Uani 1 1 d . . . . .
F15 F 0.1668(3) -0.1579(3) 0.10970(18) 0.0762(12) Uani 1 1 d . . . . .
N1 N 0.2874(2) 0.5216(3) -0.07797(14) 0.0247(8) Uani 1 1 d . . . . .
F9 F 0.4623(3) -0.1851(4) 0.0845(2) 0.1010(19) Uani 1 1 d . . . . .
F7 F 0.5296(2) -0.0841(4) 0.0499(2) 0.0965(17) Uani 1 1 d . . . . .
F11 F 0.1687(3) -0.0566(3) -0.06625(14) 0.0769(13) Uani 1 1 d . . . . .
C22 C 0.2683(3) 0.3125(4) 0.20583(19) 0.0324(10) Uani 1 1 d . . . . .
F13 F 0.0480(3) -0.0987(4) 0.0802(3) 0.115(2) Uani 1 1 d . . . . .
F4 F 0.2593(3) 0.3522(3) 0.28795(13) 0.0625(10) Uani 1 1 d . . . . .
F14 F 0.1279(4) -0.1234(4) 0.03335(16) 0.1014(19) Uani 1 1 d . . . . .
F10 F 0.2128(3) 0.0931(4) -0.09133(13) 0.0831(15) Uani 1 1 d . . . . .
C21 C 0.2835(3) 0.4245(4) 0.19588(18) 0.0300(10) Uani 1 1 d . . . . .
H21 H 0.2662 0.4826 0.2144 0.036 Uiso 1 1 calc R U . . .
F1 F 0.3177(3) 0.6456(3) 0.18609(17) 0.0713(12) Uani 1 1 d . . . . .
F3 F 0.4073(3) 0.6035(3) 0.1464(3) 0.119(2) Uani 1 1 d . . . . .
F5 F 0.1435(2) 0.3414(4) 0.23222(16) 0.0672(11) Uani 1 1 d . . . . .
C29 C 0.1242(4) -0.0871(6) 0.0771(2) 0.0500(15) Uani 1 1 d . . . . .
C5 C 0.3475(3) 0.3610(4) -0.00125(17) 0.0262(9) Uani 1 1 d . . . . .
H5 H 0.3026 0.3070 -0.0178 0.031 Uiso 1 1 calc R U . . .
F2 F 0.2795(4) 0.6138(3) 0.11051(18) 0.107(2) Uani 1 1 d . . . . .
C25 C 0.3923(3) -0.0287(4) 0.0413(2) 0.0341(11) Uani 1 1 d . . . . .
C24 C 0.4562(4) -0.1235(5) 0.0460(2) 0.0502(15) Uani 1 1 d . . . . .
F12 F 0.1274(3) 0.1035(6) -0.04930(18) 0.120(2) Uani 1 1 d . . . . .
C32 C 0.1247(3) 0.2356(5) 0.0729(2) 0.0401(12) Uani 1 1 d . . . . .
C4 C 0.3068(3) 0.4675(4) 0.01050(18) 0.0306(10) Uani 1 1 d . . . . .
H4A H 0.3506 0.5220 0.0266 0.037 Uiso 1 1 calc R U . . .
H4B H 0.2743 0.4493 0.0346 0.037 Uiso 1 1 calc R U . . .
C1 C 0.2493(3) 0.5237(4) -0.03515(18) 0.0312(10) Uani 1 1 d . . . . .
C2 C 0.2345(5) 0.6463(6) -0.0242(2) 0.0604(19) Uani 1 1 d . . . . .
H2C H 0.2873 0.6876 -0.0172 0.091 Uiso 1 1 calc R U . . .
H2D H 0.2116 0.6505 0.0047 0.091 Uiso 1 1 calc R U . . .
H2E H 0.1953 0.6800 -0.0530 0.091 Uiso 1 1 calc R U . . .
C28 C 0.1923(3) 0.0473(5) -0.0534(2) 0.0444(13) Uani 1 1 d . . . . .
C27 C 0.2640(3) 0.0540(4) -0.00625(18) 0.0305(10) Uani 1 1 d . . . . .
C23 C 0.2216(4) 0.2971(5) 0.2468(2) 0.0484(14) Uani 1 1 d . . . . .
C26 C 0.3222(3) -0.0328(4) 0.0015(2) 0.0381(12) Uani 1 1 d . . . . .
H26 H 0.3139 -0.0954 -0.0207 0.046 Uiso 1 1 calc R U . . .
C20 C 0.3233(3) 0.4540(4) 0.15965(17) 0.0279(10) Uani 1 1 d . . . . .
C30 C 0.1571(3) 0.0351(5) 0.08492(19) 0.0363(11) Uani 1 1 d . . . . .
C19 C 0.3356(4) 0.5799(5) 0.1515(2) 0.0476(14) Uani 1 1 d . . . . .
C8 C 0.2937(7) 0.3390(6) -0.1180(2) 0.087(3) Uani 1 1 d . . . . .
H8A H 0.2599 0.3019 -0.0986 0.130 Uiso 1 1 calc R U . . .
H8B H 0.3311 0.2834 -0.1268 0.130 Uiso 1 1 calc R U . . .
H8C H 0.2573 0.3709 -0.1483 0.130 Uiso 1 1 calc R U . . .
C6 C 0.3971(3) 0.3886(5) -0.0372(2) 0.0443(14) Uani 1 1 d . . . . .
H6A H 0.4270 0.3198 -0.0431 0.053 Uiso 1 1 calc R U . . .
H6B H 0.4392 0.4462 -0.0222 0.053 Uiso 1 1 calc R U . . .
C7 C 0.3445(4) 0.4330(5) -0.08730(19) 0.0419(13) Uani 1 1 d . . . . .
C3 C 0.1651(3) 0.4634(7) -0.0508(3) 0.061(2) Uani 1 1 d . . . . .
H3A H 0.1327 0.4941 -0.0827 0.091 Uiso 1 1 calc R U . . .
H3B H 0.1348 0.4754 -0.0255 0.091 Uiso 1 1 calc R U . . .
H3C H 0.1739 0.3823 -0.0544 0.091 Uiso 1 1 calc R U . . .
C9 C 0.4010(5) 0.4880(8) -0.1153(3) 0.085(3) Uani 1 1 d . . . . .
H9A H 0.3681 0.5122 -0.1481 0.127 Uiso 1 1 calc R U . . .
H9B H 0.4432 0.4335 -0.1191 0.127 Uiso 1 1 calc R U . . .
H9C H 0.4283 0.5538 -0.0967 0.127 Uiso 1 1 calc R U . . .
F8 F 0.4414(4) -0.1919(6) 0.0078(3) 0.158(4) Uani 1 1 d . . . . .
C31 C 0.0998(3) 0.1220(5) 0.0710(2) 0.0428(13) Uani 1 1 d . . . . .
H31 H 0.0424 0.1042 0.0599 0.051 Uiso 1 1 calc R U . . .
O7 O 0.19610(18) 0.2756(3) 0.08416(13) 0.0325(7) Uani 1 1 d . . . . .
O10 O 0.0349(2) 0.0617(3) 0.27073(14) 0.0371(8) Uani 1 1 d . . . . .
C14 C -0.1391(2) 0.3146(3) 0.23116(16) 0.0220(9) Uani 1 1 d . . . . .
H14 H -0.1839 0.2597 0.2328 0.026 Uiso 1 1 calc R U . . .
N3 N -0.0103(2) 0.1504(3) 0.25819(14) 0.0243(8) Uani 1 1 d . . . . .
N4 N -0.1763(2) 0.4287(3) 0.21737(14) 0.0241(8) Uani 1 1 d . . . . .
H4C H -0.2090 0.4269 0.1857 0.029 Uiso 1 1 calc R U . . .
H4D H -0.1350 0.4803 0.2196 0.029 Uiso 1 1 calc R U . . .
H4E H -0.2074 0.4484 0.2384 0.029 Uiso 1 1 calc R U . . .
C15 C -0.0764(3) 0.3216(3) 0.28164(16) 0.0227(9) Uani 1 1 d . . . . .
H15A H -0.1047 0.3504 0.3063 0.027 Uiso 1 1 calc R U . . .
H15B H -0.0327 0.3766 0.2797 0.027 Uiso 1 1 calc R U . . .
C16 C -0.0356(3) 0.2081(4) 0.29985(17) 0.0257(9) Uani 1 1 d . . . . .
C13 C -0.0956(3) 0.2748(4) 0.19311(17) 0.0269(9) Uani 1 1 d . . . . .
H13A H -0.0509 0.3290 0.1919 0.032 Uiso 1 1 calc R U . . .
H13B H -0.1357 0.2739 0.1600 0.032 Uiso 1 1 calc R U . . .
C10 C -0.0580(3) 0.1564(4) 0.20485(18) 0.0281(10) Uani 1 1 d . . . . .
C18 C -0.0934(3) 0.1307(4) 0.3193(2) 0.0384(12) Uani 1 1 d . . . . .
H18A H -0.1454 0.1204 0.2934 0.058 Uiso 1 1 calc R U . . .
H18B H -0.1053 0.1649 0.3487 0.058 Uiso 1 1 calc R U . . .
H18C H -0.0666 0.0572 0.3281 0.058 Uiso 1 1 calc R U . . .
C12 C 0.0019(3) 0.1349(5) 0.1725(2) 0.0383(12) Uani 1 1 d . . . . .
H12A H 0.0470 0.1905 0.1806 0.058 Uiso 1 1 calc R U . . .
H12B H -0.0280 0.1418 0.1374 0.058 Uiso 1 1 calc R U . . .
H12C H 0.0251 0.0586 0.1789 0.058 Uiso 1 1 calc R U . . .
F24 F 0.4005(2) -0.1536(3) 0.21257(17) 0.0733(13) Uani 1 1 d . . . . .
C35 C 0.5418(3) 0.1520(5) 0.1600(2) 0.0445(14) Uani 1 1 d . . . . .
C17 C 0.0439(3) 0.2299(5) 0.3408(2) 0.0399(13) Uani 1 1 d . . . . .
H17A H 0.0671 0.1578 0.3554 0.060 Uiso 1 1 calc R U . . .
H17B H 0.0311 0.2774 0.3666 0.060 Uiso 1 1 calc R U . . .
H17C H 0.0845 0.2685 0.3267 0.060 Uiso 1 1 calc R U . . .
C37 C 0.4642(3) 0.0126(4) 0.1921(2) 0.0393(13) Uani 1 1 d . . . . .
C11 C -0.1246(3) 0.0642(4) 0.1953(2) 0.0372(12) Uani 1 1 d . . . . .
H11A H -0.0982 -0.0096 0.2043 0.056 Uiso 1 1 calc R U . . .
H11B H -0.1545 0.0640 0.1600 0.056 Uiso 1 1 calc R U . . .
H11C H -0.1637 0.0790 0.2153 0.056 Uiso 1 1 calc R U . . .
F23 F 0.5319(3) -0.1582(4) 0.2272(3) 0.118(2) Uani 1 1 d . . . . .
F22 F 0.4771(4) -0.0590(5) 0.27253(18) 0.121(2) Uani 1 1 d . . . . .
C36 C 0.5385(3) 0.0528(5) 0.1859(2) 0.0492(16) Uani 1 1 d . . . . .
H36 H 0.5882 0.0118 0.1996 0.059 Uiso 1 1 calc R U . . .
C34 C 0.6285(3) 0.1878(5) 0.1548(4) 0.080(3) Uani 1 1 d . . . . .
C38 C 0.4676(4) -0.0902(6) 0.2266(3) 0.065(2) Uani 1 1 d . . . . .
O1W O -0.2456(3) 0.4912(3) 0.29043(16) 0.0484(10) Uani 1 1 d G . . . .
H1WA H -0.2786 0.4535 0.3041 0.073 Uiso 1 1 d G U . . .
H1WB H -0.2538 0.5616 0.2968 0.073 Uiso 1 1 d G U . . .
C33 C 0.0556(4) 0.3239(7) 0.0616(3) 0.065(2) Uani 1 1 d . . . . .
F16A F 0.0295(7) 0.3357(10) 0.0085(4) 0.0802(12) Uani 0.412(5) 1 d . . P A 1
F18A F 0.0860(7) 0.4414(11) 0.0641(5) 0.0802(12) Uani 0.412(5) 1 d . . P A 1
F17A F -0.0168(8) 0.2937(13) 0.0665(5) 0.0802(12) Uani 0.412(5) 1 d . . P A 1
F16B F -0.0203(6) 0.2764(9) 0.0448(3) 0.0802(12) Uani 0.588(5) 1 d . . P A 2
F17B F 0.0481(4) 0.3699(7) 0.1050(3) 0.0802(12) Uani 0.588(5) 1 d . . P A 2
F18B F 0.0685(5) 0.4049(8) 0.0390(4) 0.0802(12) Uani 0.588(5) 1 d . . P A 2
F19A F 0.6458(4) 0.2928(7) 0.1853(4) 0.0597(9) Uani 0.538(7) 1 d . . P B 1
F20A F 0.6317(5) 0.2090(8) 0.1151(4) 0.0597(9) Uani 0.538(7) 1 d . . P B 1
F21A F 0.6879(3) 0.1206(6) 0.1833(4) 0.0597(9) Uani 0.538(7) 1 d . . P B 1
F19B F 0.6666(5) 0.2633(9) 0.1803(4) 0.0597(9) Uani 0.462(7) 1 d . . P B 2
F20B F 0.6158(5) 0.2282(9) 0.1007(4) 0.0597(9) Uani 0.462(7) 1 d . . P B 2
F21B F 0.6818(4) 0.0977(7) 0.1510(4) 0.0597(9) Uani 0.462(7) 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Nd1 O6 2.423(3) . ?
Nd1 O9 2.449(3) . ?
Nd1 O2 2.455(3) . ?
Nd1 O4 2.456(3) . ?
Nd1 O7 2.457(3) . ?
Nd1 O8 2.477(3) . ?
Nd1 O5 2.519(3) . ?
Nd1 O3 2.543(3) . ?
Nd1 N2 2.642(4) . ?
O2 C20 1.246(6) . ?
N2 C5 1.494(5) . ?
O5 C27 1.248(6) . ?
F6 C23 1.305(7) . ?
O3 C22 1.248(6) . ?
O4 C25 1.242(6) . ?
O8 C37 1.250(6) . ?
O6 C30 1.248(6) . ?
O9 C35 1.238(6) . ?
O1 N1 1.289(5) . ?
F15 C29 1.303(8) . ?
N1 C7 1.484(6) . ?
N1 C1 1.493(6) . ?
F9 C24 1.280(8) . ?
F7 C24 1.288(7) . ?
F11 C28 1.312(7) . ?
C22 C21 1.390(7) . ?
C22 C23 1.553(8) . ?
F13 C29 1.304(7) . ?
F4 C23 1.327(7) . ?
F14 C29 1.310(7) . ?
F10 C28 1.311(7) . ?
C21 C20 1.390(7) . ?
F1 C19 1.332(7) . ?
F3 C19 1.272(7) . ?
F5 C23 1.364(8) . ?
C29 C30 1.541(8) . ?
C5 C6 1.494(7) . ?
C5 C4 1.507(6) . ?
F2 C19 1.335(8) . ?
C25 C26 1.388(7) . ?
C25 C24 1.528(7) . ?
C24 F8 1.309(8) . ?
F12 C28 1.299(7) . ?
C32 O7 1.243(6) . ?
C32 C31 1.403(9) . ?
C32 C33 1.526(8) . ?
C4 C1 1.532(6) . ?
C1 C2 1.515(8) . ?
C1 C3 1.534(7) . ?
C28 C27 1.532(7) . ?
C27 C26 1.391(7) . ?
C20 C19 1.529(7) . ?
C30 C31 1.389(8) . ?
C8 C7 1.519(10) . ?
C6 C7 1.536(7) . ?
C7 C9 1.518(9) . ?
O10 N3 1.286(5) . ?
C14 N4 1.493(5) . ?
C14 C13 1.509(6) . ?
C14 C15 1.521(6) . ?
N3 C10 1.495(6) . ?
N3 C16 1.500(6) . ?
C15 C16 1.530(6) . ?
C16 C18 1.528(7) . ?
C16 C17 1.529(6) . ?
C13 C10 1.535(6) . ?
C10 C11 1.530(7) . ?
C10 C12 1.532(7) . ?
F24 C38 1.319(7) . ?
C35 C36 1.386(8) . ?
C35 C34 1.550(8) . ?
C37 C36 1.380(8) . ?
C37 C38 1.542(8) . ?
F23 C38 1.338(9) . ?
F22 C38 1.302(10) . ?
C34 F20A 1.151(13) . ?
C34 F19B 1.213(13) . ?
C34 F21A 1.356(9) . ?
C34 F21B 1.410(12) . ?
C34 F19A 1.489(13) . ?
C34 F20B 1.544(14) . ?
C33 F18B 1.196(11) . ?
C33 F17A 1.301(16) . ?
C33 F16B 1.352(12) . ?
C33 F17B 1.363(11) . ?
C33 F16A 1.437(14) . ?
C33 F18A 1.474(16) . ?

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
O6 Nd1 O9 138.50(10) . . ?
O6 Nd1 O2 138.07(11) . . ?
O9 Nd1 O2 75.10(11) . . ?
O6 Nd1 O4 82.56(11) . . ?
O9 Nd1 O4 70.55(11) . . ?
O2 Nd1 O4 139.34(11) . . ?
O6 Nd1 O7 71.99(11) . . ?
O9 Nd1 O7 147.65(11) . . ?
O2 Nd1 O7 72.74(11) . . ?
O4 Nd1 O7 136.43(10) . . ?
O6 Nd1 O8 71.93(10) . . ?
O9 Nd1 O8 69.69(11) . . ?
O2 Nd1 O8 116.34(11) . . ?
O4 Nd1 O8 70.86(11) . . ?
O7 Nd1 O8 129.19(11) . . ?
O6 Nd1 O5 67.62(10) . . ?
O9 Nd1 O5 125.15(11) . . ?
O2 Nd1 O5 118.99(10) . . ?
O4 Nd1 O5 67.95(10) . . ?
O7 Nd1 O5 69.80(10) . . ?
O8 Nd1 O5 124.67(10) . . ?
O6 Nd1 O3 77.78(10) . . ?
O9 Nd1 O3 101.52(11) . . ?
O2 Nd1 O3 69.52(10) . . ?
O4 Nd1 O3 138.10(11) . . ?
O7 Nd1 O3 70.34(11) . . ?
O8 Nd1 O3 67.98(11) . . ?
O5 Nd1 O3 133.33(10) . . ?
O6 Nd1 N2 136.80(11) . . ?
O9 Nd1 N2 68.63(11) . . ?
O2 Nd1 N2 69.01(11) . . ?
O4 Nd1 N2 78.55(11) . . ?
O7 Nd1 N2 96.27(11) . . ?
O8 Nd1 N2 134.40(11) . . ?
O5 Nd1 N2 69.31(11) . . ?
O3 Nd1 N2 138.52(11) . . ?
C20 O2 Nd1 136.2(3) . . ?
C5 N2 Nd1 125.2(3) . . ?
C27 O5 Nd1 133.1(3) . . ?
C22 O3 Nd1 132.9(3) . . ?
C25 O4 Nd1 136.6(3) . . ?
C37 O8 Nd1 132.8(3) . . ?
C30 O6 Nd1 133.5(3) . . ?
C35 O9 Nd1 131.9(3) . . ?
O1 N1 C7 116.2(4) . . ?
O1 N1 C1 114.9(3) . . ?
C7 N1 C1 125.4(4) . . ?
O3 C22 C21 129.1(5) . . ?
O3 C22 C23 116.6(4) . . ?
C21 C22 C23 114.3(4) . . ?
C22 C21 C20 122.1(4) . . ?
F15 C29 F13 104.4(6) . . ?
F15 C29 F14 106.8(6) . . ?
F13 C29 F14 108.2(6) . . ?
F15 C29 C30 113.3(5) . . ?
F13 C29 C30 114.0(6) . . ?
F14 C29 C30 109.8(5) . . ?
C6 C5 N2 113.7(4) . . ?
C6 C5 C4 108.8(4) . . ?
N2 C5 C4 110.1(4) . . ?
O4 C25 C26 127.8(4) . . ?
O4 C25 C24 114.5(4) . . ?
C26 C25 C24 117.7(5) . . ?
F9 C24 F7 105.6(6) . . ?
F9 C24 F8 106.7(6) . . ?
F7 C24 F8 105.4(6) . . ?
F9 C24 C25 113.0(5) . . ?
F7 C24 C25 111.6(5) . . ?
F8 C24 C25 113.9(5) . . ?
O7 C32 C31 129.0(5) . . ?
O7 C32 C33 114.4(6) . . ?
C31 C32 C33 116.6(5) . . ?
C5 C4 C1 113.7(4) . . ?
N1 C1 C2 107.6(4) . . ?
N1 C1 C4 110.6(4) . . ?
C2 C1 C4 110.3(4) . . ?
N1 C1 C3 108.3(4) . . ?
C2 C1 C3 108.5(5) . . ?
C4 C1 C3 111.3(4) . . ?
F12 C28 F10 105.0(6) . . ?
F12 C28 F11 107.8(6) . . ?
F10 C28 F11 106.8(5) . . ?
F12 C28 C27 112.4(5) . . ?
F10 C28 C27 111.2(5) . . ?
F11 C28 C27 113.2(5) . . ?
O5 C27 C26 128.8(4) . . ?
O5 C27 C28 114.3(4) . . ?
C26 C27 C28 116.9(5) . . ?
F6 C23 F4 109.7(5) . . ?
F6 C23 F5 106.1(5) . . ?
F4 C23 F5 105.6(5) . . ?
F6 C23 C22 112.7(5) . . ?
F4 C23 C22 111.3(5) . . ?
F5 C23 C22 111.0(5) . . ?
C25 C26 C27 120.4(5) . . ?
O2 C20 C21 128.2(4) . . ?
O2 C20 C19 114.4(4) . . ?
C21 C20 C19 117.5(4) . . ?
O6 C30 C31 129.2(5) . . ?
O6 C30 C29 113.3(5) . . ?
C31 C30 C29 117.4(5) . . ?
F3 C19 F1 110.3(5) . . ?
F3 C19 F2 108.0(6) . . ?
F1 C19 F2 101.9(5) . . ?
F3 C19 C20 113.4(5) . . ?
F1 C19 C20 113.3(5) . . ?
F2 C19 C20 109.2(5) . . ?
C5 C6 C7 113.6(4) . . ?
N1 C7 C9 107.5(5) . . ?
N1 C7 C8 109.1(5) . . ?
C9 C7 C8 110.8(6) . . ?
N1 C7 C6 108.8(4) . . ?
C9 C7 C6 109.3(5) . . ?
C8 C7 C6 111.4(5) . . ?
C30 C31 C32 121.5(4) . . ?
C32 O7 Nd1 133.3(4) . . ?
N4 C14 C13 110.1(4) . . ?
N4 C14 C15 109.2(3) . . ?
C13 C14 C15 109.1(3) . . ?
O10 N3 C10 115.6(4) . . ?
O10 N3 C16 115.1(4) . . ?
C10 N3 C16 124.4(3) . . ?
C14 C15 C16 113.5(3) . . ?
N3 C16 C18 109.4(4) . . ?
N3 C16 C17 107.0(4) . . ?
C18 C16 C17 109.9(4) . . ?
N3 C16 C15 109.4(4) . . ?
C18 C16 C15 112.0(4) . . ?
C17 C16 C15 108.9(4) . . ?
C14 C13 C10 112.3(4) . . ?
N3 C10 C11 108.3(4) . . ?
N3 C10 C12 108.5(4) . . ?
C11 C10 C12 109.5(4) . . ?
N3 C10 C13 109.7(4) . . ?
C11 C10 C13 112.1(4) . . ?
C12 C10 C13 108.6(4) . . ?
O9 C35 C36 129.2(5) . . ?
O9 C35 C34 114.4(5) . . ?
C36 C35 C34 116.4(5) . . ?
O8 C37 C36 128.5(5) . . ?
O8 C37 C38 114.0(5) . . ?
C36 C37 C38 117.5(5) . . ?
C37 C36 C35 121.0(5) . . ?
F20A C34 F21A 118.8(9) . . ?
F19B C34 F21B 110.9(6) . . ?
F20A C34 F19A 108.5(7) . . ?
F21A C34 F19A 98.7(7) . . ?
F19B C34 F20B 105.2(8) . . ?
F21B C34 F20B 95.0(9) . . ?
F20A C34 C35 115.4(7) . . ?
F19B C34 C35 120.4(10) . . ?
F21A C34 C35 110.0(6) . . ?
F21B C34 C35 115.0(5) . . ?
F19A C34 C35 102.8(7) . . ?
F20B C34 C35 106.4(5) . . ?
F22 C38 F24 109.2(7) . . ?
F22 C38 F23 105.5(6) . . ?
F24 C38 F23 106.1(6) . . ?
F22 C38 C37 111.5(6) . . ?
F24 C38 C37 111.9(5) . . ?
F23 C38 C37 112.3(6) . . ?
F18B C33 F16B 115.5(8) . . ?
F18B C33 F17B 102.6(9) . . ?
F16B C33 F17B 100.3(7) . . ?
F17A C33 F16A 95.5(9) . . ?
F17A C33 F18A 124.8(9) . . ?
F16A C33 F18A 88.0(8) . . ?
F18B C33 C32 115.4(6) . . ?
F17A C33 C32 117.5(9) . . ?
F16B C33 C32 112.1(7) . . ?
F17B C33 C32 109.1(6) . . ?
F16A C33 C32 106.9(7) . . ?
F18A C33 C32 113.8(6) . . ?

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
C5 H5 O5 1.00 2.41 3.099(6) 125.6 .
C3 H3B F18B 0.98 2.49 3.386(11) 151.9 .
C9 H9A F19A 0.98 2.51 3.217(11) 128.4 3_665
C14 H14 F19B 1.00 2.54 3.238(9) 126.5 1_455
N4 H4C O1 0.91 1.88 2.772(5) 164.2 3_565
N4 H4D O10 0.91 1.89 2.782(5) 168.1 2
N4 H4E O1W 0.91 1.80 2.696(5) 166.6 .
C15 H15B O10 0.99 2.60 3.348(5) 132.6 2
C11 H11C F21A 0.98 2.45 3.130(8) 126.0 1_455
O1W H1WA O8 0.87 2.43 2.954(5) 119.3 2
O1W H1WA F24 0.87 2.34 3.083(6) 143.9 2
O1W H1WB F6 0.87 2.37 2.836(5) 113.6 2
O1W H1WB O3 0.87 2.09 2.954(5) 173.9 2

_refine_diff_density_max         1.413
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1978261'
loop_
_audit_author_name
_audit_author_address
'Guilherme P. Guedes'
;Universidade Federal Fluminense
Brazil
;

_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H40 Co F12 N4 O6, C4 H8 O2'
_chemical_formula_sum            'C32 H48 Co F12 N4 O8'
_chemical_formula_weight         903.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Co Co -2.3653 3.6143 '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/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.5195(3)
_cell_length_b                   19.0369(5)
_cell_length_c                   19.0330(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.392(2)
_cell_angle_gamma                90
_cell_volume                     4173.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9812
_cell_measurement_theta_min      4.47
_cell_measurement_theta_max      72.23

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             1868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    4.160
_shelx_estimated_absorpt_T_min   0.411
_shelx_estimated_absorpt_T_max   0.732

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6141
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            63286
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0868
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.283
_diffrn_reflns_theta_max         72.390
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8265
_reflns_number_gt                7039
_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_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_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)+(0.0320P)²+12.0742P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8217
_refine_ls_number_parameters     512
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0740
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1287
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.000
_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
Co1 Co 0.47468(4) 0.76355(3) 0.22572(2) 0.01160(12) Uani 1 1 d . . . . .
F12 F 0.6900(3) 0.89162(15) 0.38319(16) 0.0766(11) Uani 1 1 d . . . . .
F11 F 0.5620(2) 0.96859(17) 0.36769(15) 0.0633(9) Uani 1 1 d . . . . .
F5 F 0.88826(17) 0.64103(13) 0.18427(12) 0.0397(6) Uani 1 1 d . . . . .
O3 O 0.45713(18) 0.67947(11) 0.15753(11) 0.0153(4) Uani 1 1 d . . . . .
F7 F 0.6731(2) 0.84730(13) 0.03067(11) 0.0436(6) Uani 1 1 d . . . . .
O5 O 0.54550(19) 0.81918(12) 0.14170(11) 0.0195(5) Uani 1 1 d . . . . .
F8 F 0.5678(2) 0.93862(14) 0.04577(12) 0.0456(6) Uani 1 1 d . . . . .
F9 F 0.74683(19) 0.93800(13) 0.07875(12) 0.0417(6) Uani 1 1 d . . . . .
O4 O 0.64379(18) 0.72607(11) 0.24554(11) 0.0190(5) Uani 1 1 d . . . . .
O6 O 0.52174(18) 0.84912(11) 0.28832(11) 0.0172(5) Uani 1 1 d . . . . .
F4 F 0.8241(2) 0.6212(2) 0.28636(14) 0.0777(11) Uani 1 1 d . . . . .
F10 F 0.7265(3) 0.97966(16) 0.32098(14) 0.0658(9) Uani 1 1 d . . . . .
O2 O 0.3103(2) 0.43933(12) 0.28942(13) 0.0259(5) Uani 1 1 d . . . . .
N2 N 0.3010(2) 0.79627(13) 0.20006(12) 0.0144(5) Uani 1 1 d . . . . .
H2A H 0.2529 0.7773 0.2327 0.017 Uiso 1 1 calc R U . . .
H2B H 0.2978 0.8437 0.2055 0.017 Uiso 1 1 calc R U . . .
O8 O 0.3171(2) 0.39682(13) 0.09095(13) 0.0298(6) Uani 1 1 d . . . . .
N4 N 0.4145(2) 0.72140(13) 0.32388(12) 0.0133(5) Uani 1 1 d . . . . .
H4A H 0.4726 0.7290 0.3556 0.016 Uiso 1 1 calc R U . . .
H4B H 0.3543 0.7492 0.3372 0.016 Uiso 1 1 calc R U . . .
O7 O 0.3085(2) 0.29693(14) 0.15233(14) 0.0344(6) Uani 1 1 d . . . . .
F6 F 0.8724(2) 0.72497(19) 0.2552(2) 0.0879(13) Uani 1 1 d . . . . .
O1 O 0.0705(3) 0.80622(16) -0.05644(14) 0.0418(7) Uani 1 1 d . . . . .
N3 N 0.3328(2) 0.50494(13) 0.29801(13) 0.0159(5) Uani 1 1 d . . . . .
N1 N 0.1224(3) 0.80445(15) 0.00317(14) 0.0241(6) Uani 1 1 d . . . . .
C14 C 0.3755(2) 0.64815(15) 0.33524(15) 0.0130(6) Uani 1 1 d . . . . .
H14 H 0.3516 0.6422 0.3853 0.016 Uiso 1 1 calc R U . . .
C16 C 0.2313(3) 0.55429(17) 0.29528(17) 0.0184(7) Uani 1 1 d . . . . .
C20 C 0.5365(3) 0.64017(17) 0.13544(16) 0.0181(6) Uani 1 1 d . . . . .
C22 C 0.6955(3) 0.68049(17) 0.21020(16) 0.0192(7) Uani 1 1 d . . . . .
C27 C 0.5980(3) 0.89300(16) 0.27265(17) 0.0172(6) Uani 1 1 d . . . . .
C5 C 0.2514(3) 0.77954(16) 0.12950(15) 0.0152(6) Uani 1 1 d . . . . .
H5 H 0.2792 0.7321 0.1145 0.018 Uiso 1 1 calc R U . . .
C25 C 0.6095(3) 0.87176(17) 0.14651(16) 0.0181(7) Uani 1 1 d . . . . .
C7 C 0.2487(3) 0.82190(18) 0.00257(16) 0.0224(7) Uani 1 1 d . . . . .
C21 C 0.6526(3) 0.63865(18) 0.15612(16) 0.0201(7) Uani 1 1 d . . . . .
H21 H 0.7043 0.6080 0.1325 0.024 Uiso 1 1 calc R U . . .
C6 C 0.2920(3) 0.83402(17) 0.07721(15) 0.0181(6) Uani 1 1 d . . . . .
H6A H 0.3779 0.8344 0.0771 0.022 Uiso 1 1 calc R U . . .
H6B H 0.2656 0.8809 0.0930 0.022 Uiso 1 1 calc R U . . .
C1 C 0.0645(3) 0.76246(18) 0.05918(18) 0.0236(7) Uani 1 1 d . . . . .
C30 C 0.3625(3) 0.34628(19) 0.13019(17) 0.0244(7) Uani 1 1 d . . . . .
C13 C 0.4757(3) 0.59894(15) 0.31976(15) 0.0136(6) Uani 1 1 d . . . . .
H13A H 0.5426 0.6119 0.3499 0.016 Uiso 1 1 calc R U . . .
H13B H 0.4992 0.6053 0.2702 0.016 Uiso 1 1 calc R U . . .
C11 C 0.5400(3) 0.47738(18) 0.29683(19) 0.0249(7) Uani 1 1 d . . . . .
H11A H 0.6156 0.4877 0.3184 0.037 Uiso 1 1 calc R U . . .
H11B H 0.5219 0.4275 0.3030 0.037 Uiso 1 1 calc R U . . .
H11C H 0.5425 0.4885 0.2466 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1189(3) 0.77982(17) 0.13051(17) 0.0188(7) Uani 1 1 d . . . . .
H4C H 0.0917 0.8267 0.1456 0.023 Uiso 1 1 calc R U . . .
H4D H 0.0918 0.7451 0.1655 0.023 Uiso 1 1 calc R U . . .
C12 C 0.4423(3) 0.50380(18) 0.41011(17) 0.0222(7) Uani 1 1 d . . . . .
H12A H 0.5172 0.5149 0.4321 0.033 Uiso 1 1 calc R U . . .
H12B H 0.3810 0.5314 0.4325 0.033 Uiso 1 1 calc R U . . .
H12C H 0.4258 0.4536 0.4158 0.033 Uiso 1 1 calc R U . . .
C28 C 0.6447(3) 0.93405(18) 0.33599(18) 0.0240(7) Uani 1 1 d . . . . .
C18 C 0.1583(3) 0.5447(2) 0.3620(2) 0.0285(8) Uani 1 1 d . . . . .
H18A H 0.0918 0.5769 0.3605 0.043 Uiso 1 1 calc R U . . .
H18B H 0.1303 0.4962 0.3645 0.043 Uiso 1 1 calc R U . . .
H18C H 0.2061 0.5551 0.4035 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4467(3) 0.52173(16) 0.33191(16) 0.0162(6) Uani 1 1 d . . . . .
C24 C 0.6506(3) 0.89938(19) 0.07496(19) 0.0269(8) Uani 1 1 d . . . . .
C15 C 0.2740(3) 0.63010(16) 0.28730(16) 0.0154(6) Uani 1 1 d . . . . .
H15A H 0.2975 0.6378 0.2379 0.018 Uiso 1 1 calc R U . . .
H15B H 0.2090 0.6625 0.2974 0.018 Uiso 1 1 calc R U . . .
C19 C 0.4945(3) 0.58625(19) 0.08204(18) 0.0267(7) Uani 1 1 d . U . . .
C9 C 0.2636(3) 0.8899(2) -0.03944(18) 0.0292(8) Uani 1 1 d . . . . .
H9A H 0.3460 0.9026 -0.0407 0.044 Uiso 1 1 calc R U . . .
H9B H 0.2348 0.8828 -0.0875 0.044 Uiso 1 1 calc R U . . .
H9C H 0.2195 0.9277 -0.0170 0.044 Uiso 1 1 calc R U . . .
C23 C 0.8213(3) 0.6672(2) 0.23436(19) 0.0316(9) Uani 1 1 d . . . . .
C26 C 0.6433(3) 0.90820(18) 0.20679(18) 0.0229(7) Uani 1 1 d . . . . .
H26 H 0.6992 0.9447 0.2028 0.027 Uiso 1 1 calc R U . . .
C3 C 0.0749(3) 0.6844(2) 0.0410(2) 0.0330(9) Uani 1 1 d . . . . .
H3A H 0.0371 0.6564 0.0775 0.049 Uiso 1 1 calc R U . . .
H3B H 0.0371 0.6755 -0.0044 0.049 Uiso 1 1 calc R U . . .
H3C H 0.1570 0.6715 0.0383 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1583(3) 0.53422(19) 0.2309(2) 0.0286(8) Uani 1 1 d . . . . .
H17A H 0.0910 0.5655 0.2274 0.043 Uiso 1 1 calc R U . . .
H17B H 0.2054 0.5388 0.1885 0.043 Uiso 1 1 calc R U . . .
H17C H 0.1318 0.4855 0.2356 0.043 Uiso 1 1 calc R U . . .
C2 C -0.0634(3) 0.7844(2) 0.0591(2) 0.0343(9) Uani 1 1 d . . . . .
H2C H -0.1049 0.7580 0.0953 0.052 Uiso 1 1 calc R U . . .
H2D H -0.0691 0.8348 0.0690 0.052 Uiso 1 1 calc R U . . .
H2E H -0.0979 0.7745 0.0130 0.052 Uiso 1 1 calc R U . . .
C31 C 0.1950(3) 0.3906(2) 0.0737(2) 0.0351(9) Uani 1 1 d . . . . .
H31A H 0.1481 0.3908 0.1171 0.042 Uiso 1 1 calc R U . . .
H31B H 0.1801 0.3461 0.0484 0.042 Uiso 1 1 calc R U . . .
C8 C 0.3150(4) 0.7627(2) -0.03427(19) 0.0358(9) Uani 1 1 d . . . . .
H8A H 0.3980 0.7739 -0.0348 0.054 Uiso 1 1 calc R U . . .
H8B H 0.3030 0.7185 -0.0089 0.054 Uiso 1 1 calc R U . . .
H8C H 0.2864 0.7578 -0.0826 0.054 Uiso 1 1 calc R U . . .
C29 C 0.4888(3) 0.3577(2) 0.1452(2) 0.0361(9) Uani 1 1 d . . . . .
H29A H 0.5145 0.4009 0.1220 0.054 Uiso 1 1 calc R U . . .
H29B H 0.5010 0.3620 0.1960 0.054 Uiso 1 1 calc R U . . .
H29C H 0.5335 0.3178 0.1274 0.054 Uiso 1 1 calc R U . . .
C32 C 0.1629(3) 0.4521(2) 0.0282(2) 0.0372(9) Uani 1 1 d . . . . .
H32A H 0.0804 0.4493 0.0156 0.056 Uiso 1 1 calc R U . . .
H32B H 0.1777 0.4958 0.0538 0.056 Uiso 1 1 calc R U . . .
H32C H 0.2096 0.4512 -0.0147 0.056 Uiso 1 1 calc R U . . .
F1A F 0.5729(13) 0.5448(6) 0.0558(5) 0.0389(6) Uani 0.398(5) 1 d . U P A 1
F2A F 0.3912(6) 0.5638(4) 0.0928(4) 0.0389(6) Uani 0.398(5) 1 d . U P A 1
F3A F 0.4897(7) 0.6230(3) 0.0175(3) 0.0389(6) Uani 0.398(5) 1 d . U P A 1
F1B F 0.5709(8) 0.5363(4) 0.0680(3) 0.0389(6) Uani 0.602(5) 1 d . U P A 2
F2B F 0.4172(4) 0.5411(2) 0.1176(2) 0.0389(6) Uani 0.602(5) 1 d . U P A 2
F3B F 0.4344(4) 0.6109(2) 0.0303(2) 0.0389(6) Uani 0.602(5) 1 d . U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Co1 O3 2.070(2) . ?
Co1 O6 2.088(2) . ?
Co1 O5 2.088(2) . ?
Co1 O4 2.106(2) . ?
Co1 N2 2.149(3) . ?
Co1 N4 2.153(2) . ?
F12 C28 1.314(4) . ?
F11 C28 1.308(4) . ?
F5 C23 1.327(4) . ?
O3 C20 1.256(4) . ?
F7 C24 1.328(4) . ?
O5 C25 1.246(4) . ?
F8 C24 1.330(4) . ?
F9 C24 1.331(4) . ?
O4 C22 1.251(4) . ?
O6 C27 1.250(4) . ?
F4 C23 1.322(5) . ?
F10 C28 1.315(4) . ?
O2 N3 1.286(3) . ?
N2 C5 1.490(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
O8 C30 1.323(4) . ?
O8 C31 1.447(4) . ?
N4 C14 1.481(4) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
O7 C30 1.204(4) . ?
F6 C23 1.308(5) . ?
O1 N1 1.280(3) . ?
N3 C10 1.494(4) . ?
N3 C16 1.500(4) . ?
N1 C7 1.492(4) . ?
N1 C1 1.493(5) . ?
C14 C13 1.516(4) . ?
C14 C15 1.518(4) . ?
C14 H14 1.0000 . ?
C16 C17 1.530(5) . ?
C16 C15 1.533(4) . ?
C16 C18 1.539(5) . ?
C20 C21 1.391(5) . ?
C20 C19 1.521(5) . ?
C22 C21 1.390(5) . ?
C22 C23 1.539(5) . ?
C27 C26 1.392(5) . ?
C27 C28 1.531(4) . ?
C5 C6 1.514(4) . ?
C5 C4 1.527(4) . ?
C5 H5 1.0000 . ?
C25 C26 1.394(5) . ?
C25 C24 1.538(5) . ?
C7 C6 1.520(4) . ?
C7 C9 1.531(5) . ?
C7 C8 1.534(5) . ?
C21 H21 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C1 C4 1.527(4) . ?
C1 C3 1.530(5) . ?
C1 C2 1.531(5) . ?
C30 C29 1.496(5) . ?
C13 C10 1.525(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C11 C10 1.524(4) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C4 H4C 0.9900 . ?
C4 H4D 0.9900 . ?
C12 C10 1.528(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C19 F2A 1.282(8) . ?
C19 F3B 1.289(5) . ?
C19 F1A 1.301(14) . ?
C19 F1B 1.324(9) . ?
C19 F2B 1.413(6) . ?
C19 F3A 1.414(8) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C26 H26 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C2 H2C 0.9800 . ?
C2 H2D 0.9800 . ?
C2 H2E 0.9800 . ?
C31 C32 1.501(6) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Co1 O6 170.14(9) . . ?
O3 Co1 O5 87.08(8) . . ?
O6 Co1 O5 86.57(9) . . ?
O3 Co1 O4 86.37(8) . . ?
O6 Co1 O4 85.75(9) . . ?
O5 Co1 O4 86.75(9) . . ?
O3 Co1 N2 89.71(9) . . ?
O6 Co1 N2 98.12(9) . . ?
O5 Co1 N2 92.70(9) . . ?
O4 Co1 N2 176.06(9) . . ?
O3 Co1 N4 103.02(9) . . ?
O6 Co1 N4 83.07(9) . . ?
O5 Co1 N4 169.57(9) . . ?
O4 Co1 N4 91.23(9) . . ?
N2 Co1 N4 90.01(10) . . ?
C20 O3 Co1 127.0(2) . . ?
C25 O5 Co1 125.8(2) . . ?
C22 O4 Co1 125.6(2) . . ?
C27 O6 Co1 124.4(2) . . ?
C5 N2 Co1 119.56(18) . . ?
C5 N2 H2A 107.4 . . ?
Co1 N2 H2A 107.4 . . ?
C5 N2 H2B 107.4 . . ?
Co1 N2 H2B 107.4 . . ?
H2A N2 H2B 107.0 . . ?
C30 O8 C31 116.6(3) . . ?
C14 N4 Co1 125.26(18) . . ?
C14 N4 H4A 106.0 . . ?
Co1 N4 H4A 106.0 . . ?
C14 N4 H4B 106.0 . . ?
Co1 N4 H4B 106.0 . . ?
H4A N4 H4B 106.3 . . ?
O2 N3 C10 116.0(2) . . ?
O2 N3 C16 116.6(2) . . ?
C10 N3 C16 124.3(2) . . ?
O1 N1 C7 115.9(3) . . ?
O1 N1 C1 116.0(3) . . ?
C7 N1 C1 124.4(3) . . ?
N4 C14 C13 108.8(2) . . ?
N4 C14 C15 111.0(2) . . ?
C13 C14 C15 109.1(2) . . ?
N4 C14 H14 109.3 . . ?
C13 C14 H14 109.3 . . ?
C15 C14 H14 109.3 . . ?
N3 C16 C17 107.2(3) . . ?
N3 C16 C15 110.0(2) . . ?
C17 C16 C15 109.3(3) . . ?
N3 C16 C18 109.1(3) . . ?
C17 C16 C18 109.3(3) . . ?
C15 C16 C18 111.7(3) . . ?
O3 C20 C21 128.2(3) . . ?
O3 C20 C19 113.4(3) . . ?
C21 C20 C19 118.4(3) . . ?
O4 C22 C21 128.9(3) . . ?
O4 C22 C23 113.9(3) . . ?
C21 C22 C23 117.2(3) . . ?
O6 C27 C26 128.5(3) . . ?
O6 C27 C28 113.4(3) . . ?
C26 C27 C28 118.1(3) . . ?
N2 C5 C6 109.1(2) . . ?
N2 C5 C4 111.4(2) . . ?
C6 C5 C4 108.6(2) . . ?
N2 C5 H5 109.2 . . ?
C6 C5 H5 109.2 . . ?
C4 C5 H5 109.2 . . ?
O5 C25 C26 128.5(3) . . ?
O5 C25 C24 113.3(3) . . ?
C26 C25 C24 118.2(3) . . ?
N1 C7 C6 109.9(3) . . ?
N1 C7 C9 107.8(3) . . ?
C6 C7 C9 108.8(3) . . ?
N1 C7 C8 109.2(3) . . ?
C6 C7 C8 112.2(3) . . ?
C9 C7 C8 108.9(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 H21 118.9 . . ?
C20 C21 H21 118.9 . . ?
C5 C6 C7 114.2(3) . . ?
C5 C6 H6A 108.7 . . ?
C7 C6 H6A 108.7 . . ?
C5 C6 H6B 108.7 . . ?
C7 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
N1 C1 C4 109.7(3) . . ?
N1 C1 C3 108.8(3) . . ?
C4 C1 C3 112.3(3) . . ?
N1 C1 C2 106.7(3) . . ?
C4 C1 C2 109.3(3) . . ?
C3 C1 C2 110.0(3) . . ?
O7 C30 O8 124.2(3) . . ?
O7 C30 C29 123.4(3) . . ?
O8 C30 C29 112.4(3) . . ?
C14 C13 C10 113.5(2) . . ?
C14 C13 H13A 108.9 . . ?
C10 C13 H13A 108.9 . . ?
C14 C13 H13B 108.9 . . ?
C10 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C4 C1 113.1(3) . . ?
C5 C4 H4C 109.0 . . ?
C1 C4 H4C 109.0 . . ?
C5 C4 H4D 109.0 . . ?
C1 C4 H4D 109.0 . . ?
H4C C4 H4D 107.8 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F11 C28 F12 106.3(3) . . ?
F11 C28 F10 107.1(3) . . ?
F12 C28 F10 105.8(3) . . ?
F11 C28 C27 111.5(3) . . ?
F12 C28 C27 111.1(3) . . ?
F10 C28 C27 114.5(3) . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C10 C11 108.2(3) . . ?
N3 C10 C13 109.4(2) . . ?
C11 C10 C13 108.2(3) . . ?
N3 C10 C12 109.7(2) . . ?
C11 C10 C12 109.3(3) . . ?
C13 C10 C12 111.8(3) . . ?
F7 C24 F8 107.3(3) . . ?
F7 C24 F9 106.3(3) . . ?
F8 C24 F9 107.9(3) . . ?
F7 C24 C25 111.7(3) . . ?
F8 C24 C25 109.7(3) . . ?
F9 C24 C25 113.7(3) . . ?
C14 C15 C16 113.6(2) . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15B 108.8 . . ?
C16 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
F2A C19 F1A 120.4(8) . . ?
F3B C19 F1B 117.6(4) . . ?
F3B C19 F2B 104.5(4) . . ?
F1B C19 F2B 94.6(5) . . ?
F2A C19 F3A 105.8(5) . . ?
F1A C19 F3A 89.4(5) . . ?
F2A C19 C20 114.2(4) . . ?
F3B C19 C20 115.5(3) . . ?
F1A C19 C20 116.6(7) . . ?
F1B C19 C20 114.3(5) . . ?
F2B C19 C20 106.8(3) . . ?
F3A C19 C20 104.9(4) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
F6 C23 F4 108.8(4) . . ?
F6 C23 F5 105.7(3) . . ?
F4 C23 F5 106.2(3) . . ?
F6 C23 C22 111.9(3) . . ?
F4 C23 C22 110.5(3) . . ?
F5 C23 C22 113.5(3) . . ?
C27 C26 C25 122.2(3) . . ?
C27 C26 H26 118.9 . . ?
C25 C26 H26 118.9 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C1 C2 H2C 109.5 . . ?
C1 C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C1 C2 H2E 109.5 . . ?
H2C C2 H2E 109.5 . . ?
H2D C2 H2E 109.5 . . ?
O8 C31 C32 107.6(3) . . ?
O8 C31 H31A 110.2 . . ?
C32 C31 H31A 110.2 . . ?
O8 C31 H31B 110.2 . . ?
C32 C31 H31B 110.2 . . ?
H31A C31 H31B 108.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Co1 N4 C14 C13 61.0(3) . . . . ?
Co1 N4 C14 C15 -59.0(3) . . . . ?
O2 N3 C16 C17 -46.7(3) . . . . ?
C10 N3 C16 C17 154.1(3) . . . . ?
O2 N3 C16 C15 -165.5(2) . . . . ?
C10 N3 C16 C15 35.3(4) . . . . ?
O2 N3 C16 C18 71.5(3) . . . . ?
C10 N3 C16 C18 -87.7(3) . . . . ?
Co1 O3 C20 C21 7.0(5) . . . . ?
Co1 O3 C20 C19 -176.2(2) . . . . ?
Co1 O4 C22 C21 -7.9(5) . . . . ?
Co1 O4 C22 C23 176.2(2) . . . . ?
Co1 O6 C27 C26 20.0(5) . . . . ?
Co1 O6 C27 C28 -160.1(2) . . . . ?
Co1 N2 C5 C6 -82.6(3) . . . . ?
Co1 N2 C5 C4 157.4(2) . . . . ?
Co1 O5 C25 C26 -4.2(5) . . . . ?
Co1 O5 C25 C24 178.1(2) . . . . ?
O1 N1 C7 C6 167.1(3) . . . . ?
C1 N1 C7 C6 -35.4(4) . . . . ?
O1 N1 C7 C9 48.7(4) . . . . ?
C1 N1 C7 C9 -153.8(3) . . . . ?
O1 N1 C7 C8 -69.4(4) . . . . ?
C1 N1 C7 C8 88.1(4) . . . . ?
O4 C22 C21 C20 -3.4(5) . . . . ?
C23 C22 C21 C20 172.3(3) . . . . ?
O3 C20 C21 C22 4.1(5) . . . . ?
C19 C20 C21 C22 -172.6(3) . . . . ?
N2 C5 C6 C7 179.0(3) . . . . ?
C4 C5 C6 C7 -59.4(3) . . . . ?
N1 C7 C6 C5 45.4(4) . . . . ?
C9 C7 C6 C5 163.1(3) . . . . ?
C8 C7 C6 C5 -76.3(4) . . . . ?
O1 N1 C1 C4 -166.0(3) . . . . ?
C7 N1 C1 C4 36.5(4) . . . . ?
O1 N1 C1 C3 70.8(4) . . . . ?
C7 N1 C1 C3 -86.7(4) . . . . ?
O1 N1 C1 C2 -47.8(4) . . . . ?
C7 N1 C1 C2 154.7(3) . . . . ?
C31 O8 C30 O7 -0.7(5) . . . . ?
C31 O8 C30 C29 -179.8(3) . . . . ?
N4 C14 C13 C10 178.2(2) . . . . ?
C15 C14 C13 C10 -60.6(3) . . . . ?
N2 C5 C4 C1 -179.7(3) . . . . ?
C6 C5 C4 C1 60.1(3) . . . . ?
N1 C1 C4 C5 -47.1(4) . . . . ?
C3 C1 C4 C5 74.0(4) . . . . ?
C2 C1 C4 C5 -163.7(3) . . . . ?
O6 C27 C28 F11 -59.4(4) . . . . ?
C26 C27 C28 F11 120.5(4) . . . . ?
O6 C27 C28 F12 59.0(4) . . . . ?
C26 C27 C28 F12 -121.0(4) . . . . ?
O6 C27 C28 F10 178.8(3) . . . . ?
C26 C27 C28 F10 -1.2(5) . . . . ?
O2 N3 C10 C11 46.4(3) . . . . ?
C16 N3 C10 C11 -154.3(3) . . . . ?
O2 N3 C10 C13 164.1(2) . . . . ?
C16 N3 C10 C13 -36.6(4) . . . . ?
O2 N3 C10 C12 -72.9(3) . . . . ?
C16 N3 C10 C12 86.5(3) . . . . ?
C14 C13 C10 N3 47.5(3) . . . . ?
C14 C13 C10 C11 165.2(3) . . . . ?
C14 C13 C10 C12 -74.3(3) . . . . ?
O5 C25 C24 F7 -37.8(4) . . . . ?
C26 C25 C24 F7 144.3(3) . . . . ?
O5 C25 C24 F8 81.0(4) . . . . ?
C26 C25 C24 F8 -96.9(4) . . . . ?
O5 C25 C24 F9 -158.1(3) . . . . ?
C26 C25 C24 F9 24.0(4) . . . . ?
N4 C14 C15 C16 178.7(2) . . . . ?
C13 C14 C15 C16 58.8(3) . . . . ?
N3 C16 C15 C14 -44.6(3) . . . . ?
C17 C16 C15 C14 -162.1(3) . . . . ?
C18 C16 C15 C14 76.8(3) . . . . ?
O3 C20 C19 F2A -33.8(6) . . . . ?
C21 C20 C19 F2A 143.4(5) . . . . ?
O3 C20 C19 F3B 51.0(5) . . . . ?
C21 C20 C19 F3B -131.8(4) . . . . ?
O3 C20 C19 F1A 178.5(6) . . . . ?
C21 C20 C19 F1A -4.3(7) . . . . ?
O3 C20 C19 F1B -167.9(4) . . . . ?
C21 C20 C19 F1B 9.3(6) . . . . ?
O3 C20 C19 F2B -64.7(4) . . . . ?
C21 C20 C19 F2B 112.5(4) . . . . ?
O3 C20 C19 F3A 81.5(4) . . . . ?
C21 C20 C19 F3A -101.3(4) . . . . ?
O4 C22 C23 F6 -36.5(4) . . . . ?
C21 C22 C23 F6 147.1(3) . . . . ?
O4 C22 C23 F4 84.9(4) . . . . ?
C21 C22 C23 F4 -91.5(4) . . . . ?
O4 C22 C23 F5 -156.0(3) . . . . ?
C21 C22 C23 F5 27.6(5) . . . . ?
O6 C27 C26 C25 -2.6(6) . . . . ?
C28 C27 C26 C25 177.5(3) . . . . ?
O5 C25 C26 C27 -6.4(6) . . . . ?
C24 C25 C26 C27 171.1(3) . . . . ?
C30 O8 C31 C32 -178.8(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
N2 H2A O7 0.91 2.33 3.087(4) 140.0 2
N2 H2B O2 0.91 2.21 3.017(3) 147.8 2
N4 H4A O1 0.91 2.12 2.939(3) 149.0 4_676
N4 H4B O7 0.91 2.09 2.981(4) 164.4 2
C5 H5 O3 1.00 2.42 3.085(4) 123.3 .
C6 H6A O5 0.99 2.30 3.173(4) 146.4 .
C13 H13A O1 0.99 2.39 3.157(4) 134.1 4_676
C15 H15A O3 0.99 2.53 3.392(4) 145.6 .

_refine_diff_density_max         1.155
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 1978264'
loop_
_audit_author_name
_audit_author_address
'Guilherme P. Guedes'
;Universidade Federal Fluminense
Brazil
;

_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_THETM01_shelx               
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575
RESPONSE: We tried several crystals, but they are of poor quality and diffract
 weakly.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C76 H84 Cu4 F48 N8 O20'
_chemical_formula_sum            'C76 H84 Cu4 F48 N8 O20'
_chemical_formula_weight         2595.67

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'
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      tetragonal
_space_group_IT_number           86
_space_group_name_H-M_alt        'P 42/n'
_space_group_name_Hall           '-P 4bc'

_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+1/2, -y+1/2, z'
'-y, x+1/2, z+1/2'
'y+1/2, -x, z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y, -x-1/2, -z-1/2'
'-y-1/2, x, -z-1/2'

_cell_length_a                   18.3236(5)
_cell_length_b                   18.3236(5)
_cell_length_c                   15.2023(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5104.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6597
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      23.25

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             2608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.067
_exptl_absorpt_coefficient_mu    0.977
_shelx_estimated_absorpt_T_min   0.820
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
SADABS, Bruker Analytical X-ray Systems,Inc., Madison WI, 1997.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_method       'φ-ω scans'
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23045
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.572
_diffrn_reflns_theta_max         23.278
_diffrn_reflns_theta_full        23.278
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3688
_reflns_number_gt                3285
_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_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  
'WinGX publication routines (Farrugia, 1999) and publCIF (Westrip, 2010)'
_computing_molecular_graphics    'Mercury (Bruno, 2002)'
_computing_data_collection       'Bruker Smart (Bruker AXS, 2007)'
_computing_cell_refinement       'Bruker Smart (Bruker AXS, 2007)'
_computing_data_reduction        'Bruker Saint (Bruker AXS, 2007)'
_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)+(0.0597P)²+7.8210P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3687
_refine_ls_number_parameters     352
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.1079
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_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
Cu1 Cu 0.53667(2) 0.05650(2) 0.14207(2) 0.02510(16) Uani 1 1 d . . . . .
F6 F 0.60696(15) -0.10655(13) 0.41401(14) 0.0626(7) Uani 1 1 d . . . . .
F1 F 0.65455(13) -0.16226(12) 0.01996(14) 0.0542(6) Uani 1 1 d . . . . .
F8 F 0.61586(13) 0.25116(12) -0.09250(15) 0.0569(6) Uani 1 1 d . . . . .
O4 O 0.63943(12) 0.08315(12) 0.16549(14) 0.0318(5) Uani 1 1 d . . . . .
F9 F 0.56252(12) 0.15609(11) -0.14375(12) 0.0418(5) Uani 1 1 d . . . . .
O5 O 0.53917(12) 0.11127(12) 0.03085(14) 0.0323(5) Uani 1 1 d . . . . .
F2 F 0.73651(14) -0.1256(2) 0.1054(2) 0.1085(14) Uani 1 1 d . . . . .
F7 F 0.50331(12) 0.23133(12) -0.06415(14) 0.0518(6) Uani 1 1 d . . . . .
F11 F 0.76203(15) 0.16549(18) 0.2225(2) 0.0912(10) Uani 1 1 d . . . . .
O3 O 0.53099(11) 0.00818(11) 0.25583(14) 0.0283(5) Uani 1 1 d . . . . .
F4 F 0.59193(15) 0.00724(12) 0.42181(14) 0.0591(7) Uani 1 1 d . . . . .
F10 F 0.79964(13) 0.1603(2) 0.0900(2) 0.0949(11) Uani 1 1 d . . . . .
F12 F 0.78476(13) 0.06491(16) 0.1647(2) 0.0827(9) Uani 1 1 d . . . . .
O2 O 0.58783(12) -0.04972(12) 0.09065(14) 0.0311(5) Uani 1 1 d . . . . .
F3 F 0.6665(2) -0.21275(16) 0.14400(17) 0.0918(11) Uani 1 1 d . . . . .
O1 O 0.17750(13) 0.00544(16) 0.29730(16) 0.0484(7) Uani 1 1 d . . . . .
F5 F 0.49902(13) -0.06181(16) 0.41042(15) 0.0667(7) Uani 1 1 d . . . . .
N2 N 0.43337(16) 0.0403(2) 0.10766(19) 0.0459(8) Uani 1 1 d . . . . .
H2A H 0.4179 0.0836 0.0850 0.055 Uiso 1 1 calc R U . . .
H2B H 0.4350 0.0085 0.0617 0.055 Uiso 1 1 calc R U . . .
N1 N 0.23530(14) 0.01568(15) 0.25125(18) 0.0323(7) Uani 1 1 d . . . . .
C7 C 0.29996(19) 0.0415(2) 0.3016(2) 0.0456(10) Uani 1 1 d . . . . .
C16 C 0.58819(17) 0.15517(17) 0.0077(2) 0.0271(7) Uani 1 1 d . . . . .
C1 C 0.23814(17) -0.02257(18) 0.1649(2) 0.0303(7) Uani 1 1 d . . . . .
C5 C 0.37323(17) 0.01452(17) 0.1639(2) 0.0267(7) Uani 1 1 d . . . . .
H5 H 0.3873 -0.0338 0.1894 0.032 Uiso 1 1 calc R U . . .
C12 C 0.61166(18) -0.09287(18) 0.2355(2) 0.0324(8) Uani 1 1 d . . . . .
H12 H 0.6382 -0.1291 0.2668 0.039 Uiso 1 1 calc R U . . .
C18 C 0.67729(18) 0.12410(18) 0.1185(2) 0.0302(7) Uani 1 1 d . . . . .
C13 C 0.56975(17) -0.04443(17) 0.2828(2) 0.0275(7) Uani 1 1 d . . . . .
C17 C 0.65636(18) 0.16359(18) 0.0449(2) 0.0322(8) Uani 1 1 d . . . . .
H17 H 0.6897 0.1972 0.0195 0.039 Uiso 1 1 calc R U . . .
C11 C 0.61725(18) -0.09155(18) 0.1434(2) 0.0298(8) Uani 1 1 d . . . . .
C3 C 0.1683(2) -0.0063(2) 0.1151(3) 0.0481(10) Uani 1 1 d . . . . .
H3A H 0.1694 -0.0312 0.0580 0.072 Uiso 1 1 calc R U . . .
H3B H 0.1263 -0.0237 0.1492 0.072 Uiso 1 1 calc R U . . .
H3C H 0.1639 0.0464 0.1058 0.072 Uiso 1 1 calc R U . . .
C14 C 0.5670(2) -0.05247(19) 0.3830(2) 0.0344(8) Uani 1 1 d . . . . .
C15 C 0.56775(19) 0.19954(18) -0.0735(2) 0.0341(8) Uani 1 1 d . . . . .
C6 C 0.35951(19) 0.0666(2) 0.2381(3) 0.0417(9) Uani 1 1 d . . . . .
H6A H 0.3455 0.1146 0.2133 0.050 Uiso 1 1 calc R U . . .
H6B H 0.4054 0.0734 0.2714 0.050 Uiso 1 1 calc R U . . .
C4 C 0.30384(18) 0.0049(2) 0.1125(2) 0.0372(8) Uani 1 1 d . . . . .
H4A H 0.3133 -0.0298 0.0639 0.045 Uiso 1 1 calc R U . . .
H4B H 0.2908 0.0524 0.0857 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6691(2) -0.1490(2) 0.1034(2) 0.0435(9) Uani 1 1 d . . . . .
C19 C 0.7567(2) 0.1291(2) 0.1483(3) 0.0420(9) Uani 1 1 d . . . . .
C9 C 0.3274(2) -0.0214(3) 0.3599(3) 0.0790(18) Uani 1 1 d . . . . .
H9A H 0.3701 -0.0051 0.3935 0.118 Uiso 1 1 calc R U . . .
H9B H 0.2887 -0.0361 0.4006 0.118 Uiso 1 1 calc R U . . .
H9C H 0.3410 -0.0629 0.3228 0.118 Uiso 1 1 calc R U . . .
C8 C 0.2747(3) 0.1050(4) 0.3591(4) 0.109(3) Uani 1 1 d . . . . .
H8A H 0.3161 0.1235 0.3933 0.164 Uiso 1 1 calc R U . . .
H8B H 0.2555 0.1441 0.3216 0.164 Uiso 1 1 calc R U . . .
H8C H 0.2363 0.0882 0.3991 0.164 Uiso 1 1 calc R U . . .
C2 C 0.2439(2) -0.1047(2) 0.1811(3) 0.0544(11) Uani 1 1 d . . . . .
H2C H 0.2458 -0.1304 0.1246 0.082 Uiso 1 1 calc R U . . .
H2D H 0.2883 -0.1151 0.2147 0.082 Uiso 1 1 calc R U . . .
H2E H 0.2012 -0.1213 0.2145 0.082 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 1.946(2) . ?
Cu1 O5 1.967(2) . ?
Cu1 O4 1.978(2) . ?
Cu1 N2 1.986(3) . ?
Cu1 O2 2.297(2) . ?
F6 C14 1.319(4) . ?
F1 C10 1.320(4) . ?
F8 C15 1.325(4) . ?
O4 C18 1.247(4) . ?
F9 C15 1.335(4) . ?
O5 C16 1.256(4) . ?
F2 C10 1.307(5) . ?
F7 C15 1.324(4) . ?
F11 C19 1.315(5) . ?
O3 C13 1.266(4) . ?
F4 C14 1.324(4) . ?
F10 C19 1.315(4) . ?
F12 C19 1.308(5) . ?
O2 C11 1.234(4) . ?
F3 C10 1.321(5) . ?
O1 N1 1.283(3) . ?
F5 C14 1.324(4) . ?
N2 C5 1.472(4) . ?
N1 C7 1.487(4) . ?
N1 C1 1.489(4) . ?
C7 C8 1.527(6) . ?
C7 C6 1.527(5) . ?
C7 C9 1.538(6) . ?
C16 C17 1.380(5) . ?
C16 C15 1.525(5) . ?
C1 C3 1.517(5) . ?
C1 C4 1.529(5) . ?
C1 C2 1.529(5) . ?
C5 C6 1.500(5) . ?
C5 C4 1.503(5) . ?
C12 C13 1.376(5) . ?
C12 C11 1.403(5) . ?
C18 C17 1.387(5) . ?
C18 C19 1.527(5) . ?
C13 C14 1.532(5) . ?
C11 C10 1.543(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O5 176.02(9) . . ?
O3 Cu1 O4 90.19(9) . . ?
O5 Cu1 O4 90.38(9) . . ?
O3 Cu1 N2 96.60(11) . . ?
O5 Cu1 N2 82.65(11) . . ?
O4 Cu1 N2 172.66(11) . . ?
O3 Cu1 O2 86.49(8) . . ?
O5 Cu1 O2 97.49(9) . . ?
O4 Cu1 O2 83.22(9) . . ?
N2 Cu1 O2 99.93(12) . . ?
C18 O4 Cu1 125.1(2) . . ?
C16 O5 Cu1 125.8(2) . . ?
C13 O3 Cu1 127.2(2) . . ?
C11 O2 Cu1 118.9(2) . . ?
C5 N2 Cu1 127.5(2) . . ?
O1 N1 C7 115.1(3) . . ?
O1 N1 C1 116.2(3) . . ?
C7 N1 C1 125.1(3) . . ?
N1 C7 C8 107.2(3) . . ?
N1 C7 C6 109.9(3) . . ?
C8 C7 C6 110.4(4) . . ?
N1 C7 C9 108.6(4) . . ?
C8 C7 C9 109.8(4) . . ?
C6 C7 C9 110.9(3) . . ?
O5 C16 C17 127.1(3) . . ?
O5 C16 C15 113.1(3) . . ?
C17 C16 C15 119.7(3) . . ?
N1 C1 C3 108.6(3) . . ?
N1 C1 C4 109.4(3) . . ?
C3 C1 C4 109.9(3) . . ?
N1 C1 C2 108.9(3) . . ?
C3 C1 C2 109.4(3) . . ?
C4 C1 C2 110.7(3) . . ?
N2 C5 C6 111.0(3) . . ?
N2 C5 C4 111.6(3) . . ?
C6 C5 C4 108.9(3) . . ?
C13 C12 C11 123.4(3) . . ?
O4 C18 C17 128.5(3) . . ?
O4 C18 C19 113.4(3) . . ?
C17 C18 C19 118.1(3) . . ?
O3 C13 C12 129.4(3) . . ?
O3 C13 C14 112.1(3) . . ?
C12 C13 C14 118.4(3) . . ?
C16 C17 C18 121.5(3) . . ?
O2 C11 C12 128.9(3) . . ?
O2 C11 C10 115.9(3) . . ?
C12 C11 C10 115.2(3) . . ?
F6 C14 F4 105.7(3) . . ?
F6 C14 F5 108.2(3) . . ?
F4 C14 F5 106.9(3) . . ?
F6 C14 C13 114.2(3) . . ?
F4 C14 C13 110.6(3) . . ?
F5 C14 C13 110.9(3) . . ?
F7 C15 F8 107.6(3) . . ?
F7 C15 F9 106.5(3) . . ?
F8 C15 F9 107.4(3) . . ?
F7 C15 C16 111.5(3) . . ?
F8 C15 C16 113.2(3) . . ?
F9 C15 C16 110.3(3) . . ?
C5 C6 C7 113.7(3) . . ?
C5 C4 C1 115.7(3) . . ?
F2 C10 F1 105.9(3) . . ?
F2 C10 F3 108.3(4) . . ?
F1 C10 F3 106.2(3) . . ?
F2 C10 C11 110.4(3) . . ?
F1 C10 C11 112.3(3) . . ?
F3 C10 C11 113.4(3) . . ?
F12 C19 F11 105.2(3) . . ?
F12 C19 F10 106.6(3) . . ?
F11 C19 F10 108.3(3) . . ?
F12 C19 C18 112.2(3) . . ?
F11 C19 C18 110.8(3) . . ?
F10 C19 C18 113.4(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
N2 H2A F1 0.91 2.53 3.370(4) 154.2 5_655
N2 H2B O2 0.91 2.47 3.045(4) 121.3 5_655
C5 H5 F9 1.00 2.52 3.354(4) 140.8 5_655

_refine_diff_density_max         0.532
_refine_diff_density_min         -0.425
_refine_diff_density_rms         0.069

