# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 1942720'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cu F12 N4 O6'
_chemical_formula_sum            'C22 H14 Cu F12 N4 O6'
_chemical_formula_weight         721.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.7980(14)
_cell_length_b                   9.4558(18)
_cell_length_c                   9.9430(15)
_cell_angle_alpha                86.776(15)
_cell_angle_beta                 73.162(14)
_cell_angle_gamma                63.012(18)
_cell_volume                     702.8(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.2880
_cell_measurement_theta_min      3.7750
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    0.901
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             359
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6111
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.983
_diffrn_reflns_theta_min         3.798
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1978
_reflns_number_total             2755
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.145
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     114
_refine_ls_R_factor_all          0.0997
_refine_ls_R_factor_gt           0.0704
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1091P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1761
_refine_ls_wR_factor_ref         0.1927
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 F5A-C5 = C5-F4A = C5-F6A = C5-F4B = C5-F6B = C5-F5B
 1.32 with sigma of 0.01
 F1A-C1 = C1-F3A = C1-F2A = C1-F3B = C1-F2B = C1-F1B
 1.32 with sigma of 0.01
 F3A-F2A \\sim F3A-F1A \\sim F2A-F1A \\sim F3B-F2B \\sim F3B-F1B \\sim F2B-F1B
 with sigma of 0.02
 F5A-F4A \\sim F5A-F6A \\sim F4A-F6A \\sim F4B-F5B \\sim F4B-F6B \\sim F5B-F6B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F6A, F5A, F4A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6B, F5B, F4B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2A, F1A, F3A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2B, F1B, F3B, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F4B)=Sof(F5B)=Sof(F6B)=1-FVAR(1)
 Sof(F5A)=Sof(F4A)=Sof(F6A)=FVAR(1)
 Sof(F3B)=Sof(F2B)=Sof(F1B)=1-FVAR(2)
 Sof(F3A)=Sof(F2A)=Sof(F1A)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C9(H9), C6(H6), C10(H10), C3(H3A)
5.b Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.0490(3) Uani 1 2 d S T P . .
O1 O 0.3003(4) 0.6404(4) 0.6668(3) 0.0577(9) Uani 1 1 d . . . . .
O2 O 0.5057(5) 0.2940(4) 0.6366(3) 0.0621(9) Uani 1 1 d . . . . .
N1 N 0.3192(5) 0.4943(4) 0.4166(4) 0.0512(9) Uani 1 1 d . . . . .
O3 O -0.3211(6) 1.0263(5) 0.4370(5) 0.0972(14) Uani 1 1 d . . . . .
H3 H -0.360566 1.093876 0.502963 0.146 Uiso 1 1 calc GR . . . .
N2 N -0.1661(6) 0.8986(5) 0.4484(5) 0.0718(12) Uani 1 1 d . . . . .
C11 C -0.1136(7) 0.7881(6) 0.3605(5) 0.0629(13) Uani 1 1 d . . . . .
H11 H -0.176132 0.799234 0.296292 0.076 Uiso 1 1 calc R . . . .
C7 C 0.0478(6) 0.6374(6) 0.3553(5) 0.0540(11) Uani 1 1 d . . . . .
C8 C 0.0768(7) 0.4986(6) 0.2898(5) 0.0624(13) Uani 1 1 d . . . . .
H8 H -0.002823 0.499443 0.244892 0.075 Uiso 1 1 calc R . . . .
C9 C 0.2249(7) 0.3589(6) 0.2919(6) 0.0654(14) Uani 1 1 d . . . . .
H9 H 0.244716 0.263732 0.250924 0.078 Uiso 1 1 calc R . . . .
C2 C 0.2687(6) 0.6099(6) 0.7919(5) 0.0577(12) Uani 1 1 d . . . . .
C4 C 0.4483(7) 0.3187(6) 0.7671(5) 0.0566(12) Uani 1 1 d . . . . .
C6 C 0.1714(6) 0.6302(5) 0.4176(5) 0.0527(11) Uani 1 1 d . . . . .
H6 H 0.152282 0.723027 0.462525 0.063 Uiso 1 1 calc R . . . .
C10 C 0.3413(7) 0.3616(5) 0.3541(5) 0.0573(12) Uani 1 1 d . . . . .
H10 H 0.441708 0.266566 0.353465 0.069 Uiso 1 1 calc R . . . .
F3A F 0.078(2) 0.7356(15) 1.0237(10) 0.154(7) Uani 0.61(3) 1 d D U . A 1
F2A F 0.1965(18) 0.8587(14) 0.8841(16) 0.121(4) Uani 0.61(3) 1 d D U . A 1
C3 C 0.3367(7) 0.4641(6) 0.8487(6) 0.0692(15) Uani 1 1 d . . . . .
H3A H 0.306299 0.463467 0.946396 0.083 Uiso 1 1 calc R . . . .
C1 C 0.1300(8) 0.7577(7) 0.8933(5) 0.0817(16) Uani 1 1 d D U . . .
F1A F -0.0117(14) 0.8328(17) 0.8492(15) 0.132(5) Uani 0.61(3) 1 d D U . A 1
C5 C 0.5085(8) 0.1705(7) 0.8467(6) 0.0834(16) Uani 1 1 d D U . . .
F5A F 0.6849(11) 0.096(2) 0.8069(18) 0.136(6) Uani 0.52(2) 1 d D U . B 1
F4A F 0.458(3) 0.1864(17) 0.9811(8) 0.136(7) Uani 0.52(2) 1 d D U . B 1
F6A F 0.471(3) 0.0629(13) 0.8057(19) 0.127(7) Uani 0.52(2) 1 d D U . B 1
F4B F 0.562(3) 0.190(2) 0.9506(18) 0.142(8) Uani 0.48(2) 1 d D U . B 2
F5B F 0.627(3) 0.0414(13) 0.7731(15) 0.168(10) Uani 0.48(2) 1 d D U . B 2
F6B F 0.3682(16) 0.148(2) 0.915(2) 0.141(8) Uani 0.48(2) 1 d D U . B 2
F3B F -0.0298(18) 0.765(4) 0.927(3) 0.166(11) Uani 0.39(3) 1 d D U . A 2
F2B F 0.166(3) 0.744(2) 1.0155(15) 0.128(8) Uani 0.39(3) 1 d D U . A 2
F1B F 0.117(4) 0.8936(16) 0.854(2) 0.167(11) Uani 0.39(3) 1 d D U . 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 O1 2.010(3) . ?
Cu1 O1 2.010(3) 2_666 ?
Cu1 O2 2.301(3) . ?
Cu1 O2 2.300(3) 2_666 ?
Cu1 N1 2.017(4) . ?
Cu1 N1 2.017(4) 2_666 ?
O1 C2 1.242(6) . ?
O2 C4 1.241(6) . ?
N1 C6 1.349(6) . ?
N1 C10 1.340(5) . ?
O3 N2 1.382(6) . ?
N2 C11 1.225(6) . ?
C11 C7 1.476(7) . ?
C7 C8 1.381(6) . ?
C7 C6 1.375(7) . ?
C8 C9 1.376(7) . ?
C9 C10 1.349(7) . ?
C2 C3 1.391(7) . ?
C2 C1 1.535(7) . ?
C4 C3 1.397(7) . ?
C4 C5 1.521(8) . ?
F3A C1 1.283(8) . ?
F2A C1 1.315(8) . ?
C1 F1A 1.315(7) . ?
C1 F3B 1.318(9) . ?
C1 F2B 1.325(9) . ?
C1 F1B 1.286(9) . ?
C5 F5A 1.321(8) . ?
C5 F4A 1.275(8) . ?
C5 F6A 1.318(7) . ?
C5 F4B 1.305(8) . ?
C5 F5B 1.271(8) . ?
C5 F6B 1.327(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_666 ?
O1 Cu1 O2 95.12(12) 2_666 . ?
O1 Cu1 O2 95.12(12) . 2_666 ?
O1 Cu1 O2 84.88(12) 2_666 2_666 ?
O1 Cu1 O2 84.88(12) . . ?
O1 Cu1 N1 89.67(14) . . ?
O1 Cu1 N1 90.33(14) 2_666 . ?
O1 Cu1 N1 90.33(14) . 2_666 ?
O1 Cu1 N1 89.67(14) 2_666 2_666 ?
O2 Cu1 O2 180.00(19) 2_666 . ?
N1 Cu1 O2 86.95(14) . 2_666 ?
N1 Cu1 O2 93.05(14) 2_666 2_666 ?
N1 Cu1 O2 93.05(14) . . ?
N1 Cu1 O2 86.95(14) 2_666 . ?
N1 Cu1 N1 180.0 . 2_666 ?
C2 O1 Cu1 127.8(3) . . ?
C4 O2 Cu1 120.0(3) . . ?
C6 N1 Cu1 119.6(3) . . ?
C10 N1 Cu1 123.1(3) . . ?
C10 N1 C6 117.3(4) . . ?
C11 N2 O3 111.3(5) . . ?
N2 C11 C7 120.8(5) . . ?
C8 C7 C11 120.7(5) . . ?
C6 C7 C11 121.2(4) . . ?
C6 C7 C8 118.1(4) . . ?
C9 C8 C7 119.1(5) . . ?
C10 C9 C8 119.3(4) . . ?
O1 C2 C3 129.3(4) . . ?
O1 C2 C1 112.6(5) . . ?
C3 C2 C1 118.0(5) . . ?
O2 C4 C3 128.3(5) . . ?
O2 C4 C5 115.1(4) . . ?
C3 C4 C5 116.6(5) . . ?
N1 C6 C7 122.9(4) . . ?
N1 C10 C9 123.2(5) . . ?
C2 C3 C4 123.6(5) . . ?
F3A C1 C2 117.0(7) . . ?
F3A C1 F2A 108.5(9) . . ?
F3A C1 F1A 108.3(8) . . ?
F2A C1 C2 107.9(7) . . ?
F2A C1 F1A 104.5(8) . . ?
F1A C1 C2 109.8(6) . . ?
F3B C1 C2 111.0(9) . . ?
F3B C1 F2B 103.4(9) . . ?
F2B C1 C2 109.5(9) . . ?
F1B C1 C2 117.2(10) . . ?
F1B C1 F3B 108.6(10) . . ?
F1B C1 F2B 106.2(10) . . ?
F5A C5 C4 108.5(8) . . ?
F4A C5 C4 118.8(8) . . ?
F4A C5 F5A 106.4(9) . . ?
F4A C5 F6A 108.3(8) . . ?
F6A C5 C4 111.7(6) . . ?
F6A C5 F5A 101.6(8) . . ?
F4B C5 C4 112.3(9) . . ?
F4B C5 F6B 101.6(8) . . ?
F5B C5 C4 116.3(8) . . ?
F5B C5 F4B 108.5(10) . . ?
F5B C5 F6B 107.6(9) . . ?
F6B C5 C4 109.3(7) . . ?

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
_geom_hbond_publ_flag
O3 H3 O2 0.82 2.02 2.825(5) 166.1 1_465 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_2a
_database_code_depnum_ccdc_archive 'CCDC 1942721'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Cu F12 N4 O6'
_chemical_formula_sum            'C24 H18 Cu F12 N4 O6'
_chemical_formula_weight         749.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5710(4)
_cell_length_b                   8.6068(5)
_cell_length_c                   10.9486(6)
_cell_angle_alpha                96.577(5)
_cell_angle_beta                 106.692(6)
_cell_angle_gamma                102.284(5)
_cell_volume                     742.49(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2386
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.7600
_cell_measurement_theta_min      3.8340
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.754
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87309
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7122
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         3.711
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2846
_reflns_number_total             3594
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.068
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.2210P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-F1B = C1-F3B = C1-F2A = C1-F1A = C1-F3A = C1-F2B
 1.32 with sigma of 0.01
 F1B-F3B \\sim F1B-F2B \\sim F3B-F2B \\sim F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F1B, F2B, F3B, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F3A, F1A, F2A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F3B)=Sof(F2B)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(F3A)=Sof(F2A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C3(H3A), C10(H10), C8(H8), C9(H9)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.04880(15) Uani 1 2 d S T P . .
O2 O 0.7075(2) 0.7013(2) 0.64091(17) 0.0620(5) Uani 1 1 d . . . . .
O1 O 0.3480(2) 0.6522(2) 0.49565(16) 0.0610(4) Uani 1 1 d . . . . .
F4 F 0.9743(2) 0.9345(2) 0.7917(2) 0.0948(6) Uani 1 1 d . . . . .
N1 N 0.5582(2) 0.5799(2) 0.34833(18) 0.0519(5) Uani 1 1 d . . . . .
F5 F 0.8218(3) 1.0787(3) 0.8332(2) 0.1216(9) Uani 1 1 d . . . . .
F6 F 0.8305(3) 0.8646(3) 0.91144(18) 0.1200(8) Uani 1 1 d . . . . .
N2 N 0.1843(3) 0.5856(3) 0.01364(19) 0.0596(5) Uani 1 1 d . . . . .
O3 O 0.0631(3) 0.6057(3) -0.0964(2) 0.0835(6) Uani 1 1 d . . . . .
C7 C 0.4711(3) 0.6500(3) 0.1371(2) 0.0512(5) Uani 1 1 d . . . . .
C6 C 0.4392(3) 0.5999(3) 0.2461(2) 0.0504(5) Uani 1 1 d . . . . .
H6 H 0.328910 0.579249 0.247870 0.061 Uiso 1 1 calc R . . . .
F1A F 0.185(3) 0.934(3) 0.4627(19) 0.168(10) Uani 0.242(14) 1 d D U . A 1
F3A F 0.090(2) 0.745(2) 0.546(2) 0.134(8) Uani 0.242(14) 1 d D U . A 1
C2 C 0.3807(3) 0.7865(3) 0.5686(2) 0.0494(5) Uani 1 1 d . . . . .
C3 C 0.5304(3) 0.8737(3) 0.6605(2) 0.0546(6) Uani 1 1 d . . . . .
H3A H 0.532571 0.972977 0.705461 0.066 Uiso 1 1 calc R . . . .
C4 C 0.6793(3) 0.8230(3) 0.6907(2) 0.0479(5) Uani 1 1 d . . . . .
C11 C 0.3330(3) 0.6648(3) 0.0250(2) 0.0576(6) Uani 1 1 d . . . . .
C5 C 0.8282(3) 0.9275(3) 0.8068(2) 0.0620(6) Uani 1 1 d . . . . .
C10 C 0.7188(3) 0.6135(3) 0.3476(3) 0.0619(7) Uani 1 1 d . . . . .
H10 H 0.802929 0.601164 0.418634 0.074 Uiso 1 1 calc R . . . .
C8 C 0.6379(3) 0.6840(3) 0.1394(3) 0.0643(7) Uani 1 1 d . . . . .
H8 H 0.666029 0.719371 0.069487 0.077 Uiso 1 1 calc R . . . .
C1 C 0.2272(4) 0.8545(4) 0.5522(3) 0.0747(8) Uani 1 1 d D U . . .
C9 C 0.7615(3) 0.6656(4) 0.2447(3) 0.0708(8) Uani 1 1 d . . . . .
H9 H 0.873150 0.688140 0.246324 0.085 Uiso 1 1 calc R . . . .
F2A F 0.2453(17) 0.952(2) 0.6642(11) 0.096(4) Uani 0.242(14) 1 d D U . A 1
C12 C 0.3712(5) 0.7656(4) -0.0709(3) 0.0915(10) Uani 1 1 d . . . . .
H12A H 0.382674 0.698024 -0.142206 0.137 Uiso 1 1 calc GR . . . .
H12B H 0.474520 0.848106 -0.029368 0.137 Uiso 1 1 calc GR . . . .
H12C H 0.281044 0.815346 -0.102582 0.137 Uiso 1 1 calc GR . . . .
H3 H -0.032(6) 0.561(6) -0.086(4) 0.144(19) Uiso 1 1 d . . . . .
F3B F 0.1149(7) 0.7618(9) 0.5886(7) 0.1179(19) Uani 0.758(14) 1 d D U . A 2
F2B F 0.2593(7) 1.0050(7) 0.6072(10) 0.167(3) Uani 0.758(14) 1 d D U . A 2
F1B F 0.1541(6) 0.8516(7) 0.4271(4) 0.1159(17) Uani 0.758(14) 1 d D U . 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 O2 2.2463(17) 2_666 ?
Cu1 O2 2.2463(17) . ?
Cu1 O1 2.0300(18) . ?
Cu1 O1 2.0300(18) 2_666 ?
Cu1 N1 2.018(2) 2_666 ?
Cu1 N1 2.017(2) . ?
O2 C4 1.227(3) . ?
O1 C2 1.255(3) . ?
F4 C5 1.299(3) . ?
N1 C6 1.336(3) . ?
N1 C10 1.348(3) . ?
F5 C5 1.317(3) . ?
F6 C5 1.319(3) . ?
N2 O3 1.402(3) . ?
N2 C11 1.274(3) . ?
C7 C6 1.393(3) . ?
C7 C11 1.480(3) . ?
C7 C8 1.389(3) . ?
F1A C1 1.274(8) . ?
F3A C1 1.320(8) . ?
C2 C3 1.377(3) . ?
C2 C1 1.523(4) . ?
C3 C4 1.399(3) . ?
C4 C5 1.540(3) . ?
C11 C12 1.500(4) . ?
C10 C9 1.373(4) . ?
C8 C9 1.374(4) . ?
C1 F2A 1.355(8) . ?
C1 F3B 1.299(5) . ?
C1 F2B 1.300(5) . ?
C1 F1B 1.327(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 2_666 ?
O1 Cu1 O2 93.05(6) . 2_666 ?
O1 Cu1 O2 86.95(6) . . ?
O1 Cu1 O2 93.05(6) 2_666 . ?
O1 Cu1 O2 86.95(6) 2_666 2_666 ?
O1 Cu1 O1 180.0 . 2_666 ?
N1 Cu1 O2 88.83(7) 2_666 . ?
N1 Cu1 O2 91.17(7) 2_666 2_666 ?
N1 Cu1 O2 91.17(7) . . ?
N1 Cu1 O2 88.83(7) . 2_666 ?
N1 Cu1 O1 90.27(8) . 2_666 ?
N1 Cu1 O1 90.27(8) 2_666 . ?
N1 Cu1 O1 89.73(8) 2_666 2_666 ?
N1 Cu1 O1 89.73(8) . . ?
N1 Cu1 N1 180.00(11) . 2_666 ?
C4 O2 Cu1 121.83(15) . . ?
C2 O1 Cu1 127.26(16) . . ?
C6 N1 Cu1 121.13(15) . . ?
C6 N1 C10 118.4(2) . . ?
C10 N1 Cu1 120.49(18) . . ?
C11 N2 O3 112.4(2) . . ?
C6 C7 C11 121.2(2) . . ?
C8 C7 C6 116.6(2) . . ?
C8 C7 C11 122.3(2) . . ?
N1 C6 C7 123.7(2) . . ?
O1 C2 C3 129.2(2) . . ?
O1 C2 C1 112.7(2) . . ?
C3 C2 C1 118.0(2) . . ?
C2 C3 C4 124.5(2) . . ?
O2 C4 C3 129.0(2) . . ?
O2 C4 C5 114.0(2) . . ?
C3 C4 C5 116.9(2) . . ?
N2 C11 C7 116.8(2) . . ?
N2 C11 C12 122.9(3) . . ?
C7 C11 C12 120.2(3) . . ?
F4 C5 F5 105.9(2) . . ?
F4 C5 F6 106.4(2) . . ?
F4 C5 C4 113.5(2) . . ?
F5 C5 F6 107.5(2) . . ?
F5 C5 C4 113.9(2) . . ?
F6 C5 C4 109.3(2) . . ?
N1 C10 C9 121.7(3) . . ?
C9 C8 C7 120.2(2) . . ?
F1A C1 F3A 107.0(10) . . ?
F1A C1 C2 120.4(8) . . ?
F1A C1 F2A 105.7(9) . . ?
F3A C1 C2 113.2(12) . . ?
F3A C1 F2A 98.4(8) . . ?
F2A C1 C2 109.6(6) . . ?
F3B C1 C2 110.2(4) . . ?
F3B C1 F2B 111.4(5) . . ?
F3B C1 F1B 105.6(4) . . ?
F2B C1 C2 115.2(3) . . ?
F2B C1 F1B 104.6(5) . . ?
F1B C1 C2 109.3(3) . . ?
C10 C9 C8 119.5(2) . . ?

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
_geom_hbond_publ_flag
O3 H3 N2 0.87(4) 2.01(4) 2.827(3) 156(4) 2_565 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_3a
_database_code_depnum_ccdc_archive 'CCDC 1942723'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Cu F12 N4 O6'
_chemical_formula_sum            'C22 H14 Cu F12 N4 O6'
_chemical_formula_weight         721.91
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.9635(12)
_cell_length_b                   10.0912(14)
_cell_length_c                   10.3229(16)
_cell_angle_alpha                69.049(14)
_cell_angle_beta                 80.726(14)
_cell_angle_gamma                83.957(15)
_cell_volume                     667.68(19)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.0630
_cell_measurement_theta_min      3.5060
_shelx_estimated_absorpt_T_max   0.797
_shelx_estimated_absorpt_T_min   0.686
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             359
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6284
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         3.417
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2502
_reflns_number_total             2896
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.940
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     67
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+0.4565P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1261
_refine_ls_wR_factor_ref         0.1309
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 F6B-F5B \\sim F6B-F4B \\sim F5B-F4B \\sim F4A-F6A \\sim F4A-F5A \\sim F6A-F5A
 with sigma of 0.04
 C5-F6B \\sim C5-F5B \\sim C5-F4A \\sim C5-F6A \\sim C5-F4B \\sim C5-F5A
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 F6B, F4B, F5B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5A, F4A, F6A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F5B)=Sof(F6B)=Sof(F4B)=1-FVAR(1)
 Sof(F6A)=Sof(F4A)=Sof(F5A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C6(H6), C3(H3A), C10(H10), C9(H9), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.03567(18) Uani 1 2 d S T P . .
O1 O 0.6252(3) 0.4933(2) 0.6606(2) 0.0410(5) Uani 1 1 d . . . . .
O2 O 0.3253(3) 0.3106(2) 0.6602(2) 0.0451(5) Uani 1 1 d . . . . .
F2 F 0.6942(4) 0.5754(3) 0.8758(3) 0.0793(8) Uani 1 1 d . . . . .
F1 F 0.9238(3) 0.4422(3) 0.8156(2) 0.0740(7) Uani 1 1 d . . . . .
F3 F 0.7274(4) 0.3571(3) 1.0044(2) 0.0859(9) Uani 1 1 d . . . . .
N1 N 0.7184(4) 0.3639(3) 0.4493(3) 0.0378(6) Uani 1 1 d . . . . .
O3 O 1.4653(5) -0.0301(4) 0.3575(4) 0.0755(9) Uani 1 1 d D . . . .
F6A F 0.143(3) 0.163(2) 0.9924(13) 0.089(4) Uani 0.54(4) 1 d D U . A 1
N2 N 1.3315(4) 0.0587(3) 0.4070(3) 0.0535(7) Uani 1 1 d . . . . .
F4A F 0.311(4) 0.0138(17) 0.914(3) 0.117(6) Uani 0.54(4) 1 d D U . A 1
C2 C 0.6039(5) 0.4090(3) 0.7867(3) 0.0393(7) Uani 1 1 d . . . . .
C7 C 1.0407(5) 0.2546(4) 0.4719(4) 0.0475(8) Uani 1 1 d . . . . .
H7 H 1.153598 0.241502 0.513295 0.057 Uiso 1 1 calc R . . . .
C8 C 1.0271(5) 0.1887(3) 0.3762(3) 0.0422(7) Uani 1 1 d . . . . .
C4 C 0.3512(5) 0.2593(3) 0.7839(3) 0.0427(7) Uani 1 1 d . . . . .
C6 C 0.8873(5) 0.3386(4) 0.5048(3) 0.0453(8) Uani 1 1 d . . . . .
H6 H 0.900090 0.380939 0.569337 0.054 Uiso 1 1 calc R . . . .
C3 C 0.4841(6) 0.2989(4) 0.8510(3) 0.0511(9) Uani 1 1 d . . . . .
H3A H 0.490733 0.246748 0.944975 0.061 Uiso 1 1 calc R . . . .
C10 C 0.7065(5) 0.2995(4) 0.3570(4) 0.0475(8) Uani 1 1 d . . . . .
H10 H 0.591944 0.313818 0.317204 0.057 Uiso 1 1 calc R . . . .
F5A F 0.071(3) 0.131(3) 0.8158(18) 0.110(6) Uani 0.54(4) 1 d D U . A 1
C9 C 0.8550(5) 0.2134(4) 0.3182(4) 0.0481(8) Uani 1 1 d . . . . .
H9 H 0.839358 0.172134 0.253416 0.058 Uiso 1 1 calc R . . . .
C11 C 1.1857(5) 0.0958(4) 0.3393(4) 0.0506(8) Uani 1 1 d . . . . .
H11 H 1.179862 0.063713 0.266129 0.061 Uiso 1 1 calc R . . . .
C1 C 0.7395(6) 0.4447(4) 0.8729(4) 0.0539(9) Uani 1 1 d . . . . .
C5 C 0.2195(6) 0.1378(4) 0.8780(4) 0.0603(9) Uani 1 1 d D U . . .
H3 H 1.552(7) -0.049(7) 0.406(6) 0.13(3) Uiso 1 1 d D . . . .
F5B F 0.128(4) 0.086(2) 0.805(2) 0.096(5) Uani 0.46(4) 1 d D U . A 2
F6B F 0.094(4) 0.168(2) 0.973(2) 0.096(5) Uani 0.46(4) 1 d D U . A 2
F4B F 0.326(3) 0.0272(17) 0.949(3) 0.094(5) Uani 0.46(4) 1 d D U . 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 O1 1.971(2) . ?
Cu1 O1 1.971(2) 2_666 ?
Cu1 O2 2.334(2) . ?
Cu1 O2 2.334(2) 2_666 ?
Cu1 N1 2.071(3) . ?
Cu1 N1 2.071(3) 2_666 ?
O1 C2 1.271(4) . ?
O2 C4 1.231(4) . ?
F2 C1 1.333(5) . ?
F1 C1 1.326(4) . ?
F3 C1 1.324(4) . ?
N1 C6 1.351(4) . ?
N1 C10 1.348(4) . ?
O3 N2 1.389(4) . ?
F6A C5 1.316(9) . ?
N2 C11 1.273(5) . ?
F4A C5 1.299(11) . ?
C2 C3 1.363(5) . ?
C2 C1 1.544(5) . ?
C7 C8 1.392(5) . ?
C7 C6 1.369(5) . ?
C8 C9 1.385(5) . ?
C8 C11 1.465(5) . ?
C4 C3 1.405(5) . ?
C4 C5 1.544(5) . ?
C10 C9 1.383(5) . ?
F5A C5 1.318(10) . ?
C5 F5B 1.318(11) . ?
C5 F6B 1.307(11) . ?
C5 F4B 1.325(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_666 ?
O1 Cu1 O2 94.68(8) . 2_666 ?
O1 Cu1 O2 85.32(8) 2_666 2_666 ?
O1 Cu1 O2 85.32(8) . . ?
O1 Cu1 O2 94.68(8) 2_666 . ?
O1 Cu1 N1 89.23(9) . 2_666 ?
O1 Cu1 N1 90.77(9) . . ?
O1 Cu1 N1 90.77(9) 2_666 2_666 ?
O1 Cu1 N1 89.23(9) 2_666 . ?
O2 Cu1 O2 180.00(9) . 2_666 ?
N1 Cu1 O2 91.98(9) 2_666 2_666 ?
N1 Cu1 O2 88.02(9) 2_666 . ?
N1 Cu1 O2 91.98(9) . . ?
N1 Cu1 O2 88.02(9) . 2_666 ?
N1 Cu1 N1 180.0 2_666 . ?
C2 O1 Cu1 130.2(2) . . ?
C4 O2 Cu1 122.2(2) . . ?
C6 N1 Cu1 120.9(2) . . ?
C10 N1 Cu1 123.4(2) . . ?
C10 N1 C6 115.7(3) . . ?
C11 N2 O3 111.8(3) . . ?
O1 C2 C3 130.1(3) . . ?
O1 C2 C1 110.7(3) . . ?
C3 C2 C1 119.2(3) . . ?
C6 C7 C8 119.8(3) . . ?
C7 C8 C11 121.9(3) . . ?
C9 C8 C7 116.9(3) . . ?
C9 C8 C11 121.1(3) . . ?
O2 C4 C3 128.1(3) . . ?
O2 C4 C5 116.0(3) . . ?
C3 C4 C5 115.9(3) . . ?
N1 C6 C7 124.0(3) . . ?
C2 C3 C4 124.1(3) . . ?
N1 C10 C9 123.7(3) . . ?
C10 C9 C8 119.8(3) . . ?
N2 C11 C8 120.3(3) . . ?
F2 C1 C2 110.1(3) . . ?
F1 C1 F2 107.1(3) . . ?
F1 C1 C2 111.0(3) . . ?
F3 C1 F2 107.1(3) . . ?
F3 C1 F1 108.1(3) . . ?
F3 C1 C2 113.2(3) . . ?
F6A C5 C4 109.4(9) . . ?
F6A C5 F5A 106.0(11) . . ?
F4A C5 F6A 108.4(11) . . ?
F4A C5 C4 113.5(12) . . ?
F4A C5 F5A 108.1(10) . . ?
F5A C5 C4 111.2(9) . . ?
F5B C5 C4 112.7(11) . . ?
F5B C5 F4B 103.6(11) . . ?
F6B C5 C4 115.0(10) . . ?
F6B C5 F5B 109.6(12) . . ?
F6B C5 F4B 104.7(12) . . ?
F4B C5 C4 110.4(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
_geom_hbond_publ_flag
O3 H3 N2 0.811(10) 2.18(3) 2.918(5) 152(6) 2_856 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 1942722'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Cu F6 N4 O6'
_chemical_formula_sum            'C24 H24 Cu F6 N4 O6'
_chemical_formula_weight         642.01
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           92
_space_group_name_H-M_alt        'P 41 21 2'
_space_group_name_Hall           'P 4abw 2nw'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-y+1/2, x+1/2, z+1/4'
'y+1/2, -x+1/2, z+3/4'
'-x+1/2, y+1/2, -z+1/4'
'x+1/2, -y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   8.9094(2)
_cell_length_b                   8.9094(2)
_cell_length_c                   33.9781(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2697.09(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2917
_cell_measurement_temperature    200
_cell_measurement_theta_max      31.2020
_cell_measurement_theta_min      3.7740
_shelx_estimated_absorpt_T_max   0.827
_shelx_estimated_absorpt_T_min   0.715
_exptl_absorpt_coefficient_mu    0.898
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1308
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            7762
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_min         3.314
_diffrn_ambient_temperature      200
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.648
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3223
_reflns_number_total             3587
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.353
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details 
;
 Flack x determined using 1086 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.003(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         3587
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0505P)²+0.5448P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1035
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C8(H8), C9(H9), C3(H3A)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.55359(4) 0.44641(4) 0.250000 0.02777(15) Uani 1 2 d S T P . .
O1 O 0.4031(3) 0.2892(3) 0.24169(7) 0.0362(5) Uani 1 1 d . . . . .
O3 O 0.4756(3) 1.1375(3) 0.33591(8) 0.0425(7) Uani 1 1 d D . . . .
F3 F 0.3304(3) -0.0912(3) 0.23440(8) 0.0644(8) Uani 1 1 d . . . . .
O2 O 0.6946(3) 0.3252(3) 0.20829(9) 0.0497(7) Uani 1 1 d . . . . .
N1 N 0.4192(3) 0.5420(3) 0.29641(8) 0.0308(6) Uani 1 1 d . . . . .
F1 F 0.2135(3) 0.0820(3) 0.26419(8) 0.0689(8) Uani 1 1 d . . . . .
F2 F 0.2121(4) 0.0721(4) 0.20115(9) 0.0818(10) Uani 1 1 d . . . . .
N2 N 0.4740(4) 0.9828(3) 0.32806(9) 0.0369(7) Uani 1 1 d . . . . .
C6 C 0.4288(4) 0.6873(4) 0.30532(9) 0.0300(7) Uani 1 1 d . . . . .
H6 H 0.495098 0.748034 0.290276 0.036 Uiso 1 1 calc R . . . .
C7 C 0.3474(4) 0.7554(4) 0.33532(9) 0.0292(6) Uani 1 1 d . . . . .
C10 C 0.3262(4) 0.4564(4) 0.31751(9) 0.0338(7) Uani 1 1 d . . . . .
H10 H 0.317798 0.352982 0.311109 0.041 Uiso 1 1 calc R . . . .
C11 C 0.3582(4) 0.9184(4) 0.34271(9) 0.0310(7) Uani 1 1 d . . . . .
C8 C 0.2524(4) 0.6631(4) 0.35726(9) 0.0354(7) Uani 1 1 d . . . . .
H8 H 0.195162 0.703737 0.378316 0.042 Uiso 1 1 calc R . . . .
C2 C 0.4317(4) 0.1557(4) 0.23091(9) 0.0328(7) Uani 1 1 d . . . . .
C9 C 0.2420(5) 0.5120(4) 0.34811(10) 0.0380(8) Uani 1 1 d . . . . .
H9 H 0.177692 0.447778 0.362744 0.046 Uiso 1 1 calc R . . . .
C4 C 0.6880(5) 0.1857(5) 0.20475(11) 0.0419(8) Uani 1 1 d . . . . .
C3 C 0.5620(5) 0.0978(4) 0.21592(11) 0.0394(8) Uani 1 1 d . . . . .
H3A H 0.568579 -0.007986 0.212790 0.047 Uiso 1 1 calc R . . . .
C1 C 0.2954(4) 0.0545(5) 0.23302(10) 0.0409(8) Uani 1 1 d . . . . .
C12 C 0.2356(5) 0.9943(5) 0.36510(12) 0.0461(9) Uani 1 1 d . . . . .
H12A H 0.241757 0.965802 0.392913 0.069 Uiso 1 1 calc GR . . . .
H12B H 0.138133 0.963405 0.354447 0.069 Uiso 1 1 calc GR . . . .
H12C H 0.246356 1.103321 0.362638 0.069 Uiso 1 1 calc GR . . . .
C5 C 0.8185(5) 0.1054(6) 0.18635(16) 0.0639(13) Uani 1 1 d . . . . .
H5A H 0.829437 0.137656 0.158928 0.096 Uiso 1 1 calc GR . . . .
H5B H 0.800693 -0.003126 0.187191 0.096 Uiso 1 1 calc GR . . . .
H5C H 0.910370 0.129146 0.200916 0.096 Uiso 1 1 calc GR . . . .
H3 H 0.532(5) 1.167(6) 0.3191(11) 0.067(17) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.959(2) . ?
Cu1 O1 1.959(2) 8_665 ?
Cu1 O2 2.180(3) . ?
Cu1 O2 2.180(3) 8_665 ?
Cu1 N1 2.155(3) 8_665 ?
Cu1 N1 2.155(3) . ?
O1 C2 1.270(4) . ?
O3 N2 1.404(4) . ?
F3 C1 1.336(5) . ?
O2 C4 1.249(5) . ?
N1 C6 1.332(4) . ?
N1 C10 1.335(4) . ?
F1 C1 1.309(4) . ?
F2 C1 1.322(4) . ?
N2 C11 1.281(5) . ?
C6 C7 1.390(5) . ?
C7 C11 1.477(5) . ?
C7 C8 1.396(5) . ?
C10 C9 1.374(5) . ?
C11 C12 1.493(5) . ?
C8 C9 1.385(5) . ?
C2 C3 1.369(6) . ?
C2 C1 1.514(5) . ?
C4 C3 1.421(6) . ?
C4 C5 1.501(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 177.50(15) . 8_665 ?
O1 Cu1 O2 91.18(10) 8_665 . ?
O1 Cu1 O2 86.92(11) 8_665 8_665 ?
O1 Cu1 O2 86.92(11) . . ?
O1 Cu1 O2 91.18(10) . 8_665 ?
O1 Cu1 N1 91.21(10) . 8_665 ?
O1 Cu1 N1 90.46(10) . . ?
O1 Cu1 N1 91.22(10) 8_665 . ?
O1 Cu1 N1 90.46(10) 8_665 8_665 ?
O2 Cu1 O2 81.46(14) . 8_665 ?
N1 Cu1 O2 91.57(10) . 8_665 ?
N1 Cu1 O2 91.57(10) 8_665 . ?
N1 Cu1 O2 172.49(10) . . ?
N1 Cu1 O2 172.49(10) 8_665 8_665 ?
N1 Cu1 N1 95.52(14) 8_665 . ?
C2 O1 Cu1 125.0(2) . . ?
C4 O2 Cu1 121.9(3) . . ?
C6 N1 Cu1 121.0(2) . . ?
C6 N1 C10 118.2(3) . . ?
C10 N1 Cu1 120.8(2) . . ?
C11 N2 O3 111.9(3) . . ?
N1 C6 C7 123.9(3) . . ?
C6 C7 C11 121.3(3) . . ?
C6 C7 C8 116.8(3) . . ?
C8 C7 C11 121.9(3) . . ?
N1 C10 C9 122.6(3) . . ?
N2 C11 C7 115.2(3) . . ?
N2 C11 C12 125.8(3) . . ?
C7 C11 C12 118.9(3) . . ?
C9 C8 C7 119.5(3) . . ?
O1 C2 C3 129.1(3) . . ?
O1 C2 C1 112.5(3) . . ?
C3 C2 C1 118.2(3) . . ?
C10 C9 C8 118.9(3) . . ?
O2 C4 C3 124.0(4) . . ?
O2 C4 C5 118.6(4) . . ?
C3 C4 C5 117.4(4) . . ?
C2 C3 C4 124.2(4) . . ?
F3 C1 C2 113.1(3) . . ?
F1 C1 F3 106.5(3) . . ?
F1 C1 F2 109.1(4) . . ?
F1 C1 C2 112.0(3) . . ?
F2 C1 F3 106.0(3) . . ?
F2 C1 C2 110.0(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
_geom_hbond_publ_flag
O3 H3 O2 0.806(13) 2.00(3) 2.764(4) 158(6) 8_675 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_4b
_database_code_depnum_ccdc_archive 'CCDC 1942726'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 Cu F6 N4 O6'
_chemical_formula_sum            'C24 H24 Cu F6 N4 O6'
_chemical_formula_weight         642.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5478(4)
_cell_length_b                   9.2084(4)
_cell_length_c                   10.0669(5)
_cell_angle_alpha                114.584(4)
_cell_angle_beta                 99.527(4)
_cell_angle_gamma                98.514(4)
_cell_volume                     689.52(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4575
_cell_measurement_temperature    296
_cell_measurement_theta_max      28.7710
_cell_measurement_theta_min      3.9410
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.668
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79683
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) 
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             327
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10981
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         3.528
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2552
_reflns_number_total             2713
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.170
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.1282P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0952
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 C1-F1A = C1-F1B = C1-F2A = C1-F2B = C1-F3A = C1-F3B
 1.32 with sigma of 0.005
 F1A-F2A \\sim F1A-F3A \\sim F2A-F3A
 with sigma of 0.02
 F1B-F2B \\sim F1B-F3B \\sim F2B-F3B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C1, F1A, F2A, F3A, F1B, F2B, F3B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C6(H6), C7(H7), C3(H3A)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.04472(14) Uani 1 2 d S T P . .
O2 O 0.72057(18) 0.38488(18) 0.49493(17) 0.0533(4) Uani 1 1 d . . . . .
O1 O 0.44064(19) 0.40755(18) 0.63448(16) 0.0530(4) Uani 1 1 d . . . . .
N1 N 0.6339(2) 0.7143(2) 0.68351(18) 0.0456(4) Uani 1 1 d . . . . .
O3 O 0.8875(2) 1.3823(2) 1.2828(2) 0.0705(5) Uani 1 1 d D . . . .
N2 N 0.8151(2) 1.2237(2) 1.1696(2) 0.0552(4) Uani 1 1 d . . . . .
C8 C 0.7943(2) 1.0242(2) 0.9260(2) 0.0428(4) Uani 1 1 d . . . . .
C11 C 0.8704(3) 1.1913(2) 1.0515(2) 0.0478(5) Uani 1 1 d . . . . .
C9 C 0.6630(3) 0.9208(3) 0.9342(2) 0.0495(5) Uani 1 1 d . . . . .
H9 H 0.626798 0.954018 1.022051 0.059 Uiso 1 1 calc R . . . .
C10 C 0.5873(3) 0.7712(3) 0.8140(2) 0.0499(5) Uani 1 1 d . . . . .
H10 H 0.499553 0.705634 0.822557 0.060 Uiso 1 1 calc R . . . .
C6 C 0.7631(3) 0.8093(3) 0.6771(2) 0.0516(5) Uani 1 1 d . . . . .
H6 H 0.800071 0.770322 0.589753 0.062 Uiso 1 1 calc R . . . .
C7 C 0.8452(3) 0.9623(3) 0.7926(2) 0.0498(5) Uani 1 1 d . . . . .
H7 H 0.934211 1.023954 0.781664 0.060 Uiso 1 1 calc R . . . .
C4 C 0.7470(3) 0.2978(3) 0.5583(3) 0.0556(5) Uani 1 1 d . . . . .
C2 C 0.5110(3) 0.3155(3) 0.6746(2) 0.0553(5) Uani 1 1 d . . . . .
F3A F 0.2658(4) 0.1828(7) 0.6941(6) 0.1050(17) Uani 0.611(9) 1 d D U . A 1
C3 C 0.6479(3) 0.2621(4) 0.6461(3) 0.0707(7) Uani 1 1 d . . . . .
H3A H 0.679681 0.195361 0.688636 0.085 Uiso 1 1 calc R . . . .
C5 C 0.8945(3) 0.2264(4) 0.5432(4) 0.0809(8) Uani 1 1 d . . . . .
H5A H 0.905713 0.190238 0.441756 0.121 Uiso 1 1 calc GR . . . .
H5B H 0.881206 0.134601 0.565957 0.121 Uiso 1 1 calc GR . . . .
H5C H 0.990584 0.308931 0.612193 0.121 Uiso 1 1 calc GR . . . .
C12 C 0.9985(4) 1.3088(3) 1.0367(3) 0.0738(7) Uani 1 1 d . . . . .
H12A H 1.043569 1.404081 1.132530 0.111 Uiso 1 1 calc GR . . . .
H12B H 0.950673 1.341577 0.963581 0.111 Uiso 1 1 calc GR . . . .
H12C H 1.083753 1.256318 1.004419 0.111 Uiso 1 1 calc GR . . . .
F1A F 0.4063(12) 0.3717(8) 0.8881(7) 0.210(5) Uani 0.611(9) 1 d D U . A 1
C1 C 0.4212(4) 0.2563(3) 0.7680(3) 0.0835(8) Uani 1 1 d D U . . .
F2A F 0.4708(8) 0.1407(12) 0.7930(13) 0.193(5) Uani 0.611(9) 1 d D U . A 1
H3 H 0.840(4) 1.386(4) 1.347(3) 0.096(11) Uiso 1 1 d D . . . .
F1B F 0.3315(11) 0.3518(13) 0.8340(10) 0.135(5) Uani 0.389(9) 1 d D U . A 2
F2B F 0.5221(9) 0.2773(11) 0.8926(6) 0.106(3) Uani 0.389(9) 1 d D U . A 2
F3B F 0.351(2) 0.1028(9) 0.7032(12) 0.256(10) Uani 0.389(9) 1 d D U . 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 O2 2.2935(15) 2_666 ?
Cu1 O2 2.2935(15) . ?
Cu1 O1 1.9681(14) . ?
Cu1 O1 1.9681(14) 2_666 ?
Cu1 N1 2.0531(17) 2_666 ?
Cu1 N1 2.0531(17) . ?
O2 C4 1.239(3) . ?
O1 C2 1.264(3) . ?
N1 C10 1.350(2) . ?
N1 C6 1.332(3) . ?
O3 N2 1.389(2) . ?
O3 H3 0.803(10) . ?
N2 C11 1.288(3) . ?
C8 C11 1.484(3) . ?
C8 C9 1.397(3) . ?
C8 C7 1.395(3) . ?
C11 C12 1.493(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.368(3) . ?
C10 H10 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.380(3) . ?
C7 H7 0.9300 . ?
C4 C3 1.419(4) . ?
C4 C5 1.507(3) . ?
C2 C3 1.363(4) . ?
C2 C1 1.520(3) . ?
F3A C1 1.328(4) . ?
C3 H3A 0.9300 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
F1A C1 1.276(4) . ?
C1 F2A 1.303(4) . ?
C1 F1B 1.298(5) . ?
C1 F2B 1.321(4) . ?
C1 F3B 1.279(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 . 2_666 ?
O1 Cu1 O2 87.62(6) 2_666 2_666 ?
O1 Cu1 O2 87.63(6) . . ?
O1 Cu1 O2 92.38(6) . 2_666 ?
O1 Cu1 O2 92.38(6) 2_666 . ?
O1 Cu1 O1 180.0 . 2_666 ?
O1 Cu1 N1 89.63(6) 2_666 . ?
O1 Cu1 N1 90.37(6) . . ?
O1 Cu1 N1 89.63(6) . 2_666 ?
O1 Cu1 N1 90.37(6) 2_666 2_666 ?
N1 Cu1 O2 91.33(6) 2_666 2_666 ?
N1 Cu1 O2 88.67(6) 2_666 . ?
N1 Cu1 O2 88.67(6) . 2_666 ?
N1 Cu1 O2 91.33(6) . . ?
N1 Cu1 N1 180.0 2_666 . ?
C4 O2 Cu1 123.56(15) . . ?
C2 O1 Cu1 126.93(15) . . ?
C10 N1 Cu1 120.91(14) . . ?
C6 N1 Cu1 122.17(13) . . ?
C6 N1 C10 116.75(18) . . ?
N2 O3 H3 101(3) . . ?
C11 N2 O3 112.26(18) . . ?
C9 C8 C11 121.08(18) . . ?
C7 C8 C11 122.77(19) . . ?
C7 C8 C9 116.13(19) . . ?
N2 C11 C8 114.25(19) . . ?
N2 C11 C12 124.5(2) . . ?
C8 C11 C12 121.27(19) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.49(19) . . ?
C10 C9 H9 119.8 . . ?
N1 C10 C9 123.05(19) . . ?
N1 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N1 C6 H6 118.1 . . ?
N1 C6 C7 123.76(19) . . ?
C7 C6 H6 118.1 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.73(19) . . ?
C6 C7 H7 120.1 . . ?
O2 C4 C3 124.1(2) . . ?
O2 C4 C5 118.2(2) . . ?
C3 C4 C5 117.7(2) . . ?
O1 C2 C3 130.8(2) . . ?
O1 C2 C1 111.8(2) . . ?
C3 C2 C1 117.4(2) . . ?
C4 C3 H3A 116.6 . . ?
C2 C3 C4 126.8(2) . . ?
C2 C3 H3A 116.6 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
F3A C1 C2 110.7(3) . . ?
F1A C1 C2 114.3(4) . . ?
F1A C1 F3A 101.4(5) . . ?
F1A C1 F2A 112.0(5) . . ?
F2A C1 C2 115.2(3) . . ?
F2A C1 F3A 101.6(4) . . ?
F1B C1 C2 113.4(5) . . ?
F1B C1 F2B 96.6(5) . . ?
F2B C1 C2 111.6(4) . . ?
F3B C1 C2 115.1(5) . . ?
F3B C1 F1B 114.4(9) . . ?
F3B C1 F2B 103.8(8) . . ?

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
_geom_hbond_publ_flag
O3 H3 O2 0.803(10) 1.949(10) 2.751(2) 177(4) 1_566 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_5a-I
_database_code_depnum_ccdc_archive 'CCDC 1942727'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H22 Cu F12 N4 O6'
_chemical_formula_sum            'C34 H22 Cu F12 N4 O6'
_chemical_formula_weight         874.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.0451(4)
_cell_length_b                   10.1886(5)
_cell_length_c                   10.3628(4)
_cell_angle_alpha                105.030(4)
_cell_angle_beta                 97.391(4)
_cell_angle_gamma                93.535(4)
_cell_volume                     910.16(7)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3688
_cell_measurement_temperature    296
_cell_measurement_theta_max      30.3240
_cell_measurement_theta_min      2.9510
_shelx_estimated_absorpt_T_max   0.865
_shelx_estimated_absorpt_T_min   0.769
_exptl_absorpt_coefficient_mu    0.712
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79392
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             439
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8348
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_min         2.835
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3731
_reflns_number_total             4385
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.424
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4385
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0660P)²+0.1157P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1118
_refine_ls_wR_factor_ref         0.1182
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 C1-F2A = C1-F3B = C1-F1A = C1-F2B = C1-F1B = C1-F3A
 1.32 with sigma of 0.005
 F2A-F1A \\sim F2A-F3A \\sim F3B-F2B \\sim F3B-F1B \\sim F1A-F3A \\sim F2B-F1B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F1A, F2A, F3A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F2B, F1B, F3B, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F1B)=Sof(F2B)=Sof(F3B)=1-FVAR(1)
 Sof(F2A)=Sof(F3A)=Sof(F1A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C3(H3A), C13(H13), C17(H17), C14(H14),
 C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.03656(12) Uani 1 2 d S T P . .
O1 O 0.70406(16) 0.58429(15) 0.49957(15) 0.0445(3) Uani 1 1 d . . . . .
O2 O 0.46739(17) 0.71291(15) 0.64053(14) 0.0482(4) Uani 1 1 d . . . . .
N1 N 0.58139(19) 0.42892(16) 0.65565(16) 0.0383(4) Uani 1 1 d . . . . .
O3 O 0.7678(3) 0.2674(2) 1.19762(19) 0.0754(6) Uani 1 1 d D . . . .
F6 F 0.3386(2) 0.94700(19) 0.6486(2) 0.0993(6) Uani 1 1 d . . . . .
F5 F 0.5469(3) 1.05722(17) 0.6583(3) 0.1102(7) Uani 1 1 d . . . . .
N2 N 0.6980(3) 0.3074(2) 1.08884(19) 0.0583(5) Uani 1 1 d . . . . .
C6 C 0.5044(2) 0.4217(2) 0.7577(2) 0.0422(4) Uani 1 1 d . . . . .
H6 H 0.408272 0.449566 0.754925 0.051 Uiso 1 1 calc R . . . .
C7 C 0.5613(2) 0.3754(2) 0.8647(2) 0.0433(5) Uani 1 1 d . . . . .
H7 H 0.503232 0.370380 0.931422 0.052 Uiso 1 1 calc R . . . .
C8 C 0.7064(2) 0.3357(2) 0.87385(19) 0.0392(4) Uani 1 1 d . . . . .
C9 C 0.7849(2) 0.3436(2) 0.7679(2) 0.0444(5) Uani 1 1 d . . . . .
H9 H 0.881948 0.318168 0.768906 0.053 Uiso 1 1 calc R . . . .
C12 C 0.9272(2) 0.2404(2) 0.9904(2) 0.0437(5) Uani 1 1 d . . . . .
C10 C 0.7197(2) 0.3887(2) 0.6628(2) 0.0447(5) Uani 1 1 d . . . . .
H10 H 0.773919 0.391436 0.592977 0.054 Uiso 1 1 calc R . . . .
C2 C 0.7467(2) 0.7089(2) 0.5227(2) 0.0454(5) Uani 1 1 d . . . . .
F4 F 0.4986(3) 0.9814(2) 0.8238(2) 0.1298(10) Uani 1 1 d . . . . .
C11 C 0.7765(2) 0.2918(2) 0.9915(2) 0.0434(5) Uani 1 1 d . . . . .
C4 C 0.5432(3) 0.8154(2) 0.6325(2) 0.0470(5) Uani 1 1 d . . . . .
C3 C 0.6772(3) 0.8213(2) 0.5790(3) 0.0557(6) Uani 1 1 d . . . . .
H3A H 0.721906 0.906878 0.581854 0.067 Uiso 1 1 calc R . . . .
F1B F 1.0124(10) 0.726(3) 0.5638(15) 0.155(7) Uani 0.367(17) 1 d D U . A 1
C13 C 0.9517(3) 0.1259(3) 0.8930(2) 0.0562(6) Uani 1 1 d . . . . .
H13 H 0.872094 0.078385 0.828495 0.067 Uiso 1 1 calc R . . . .
C17 C 1.0471(3) 0.3079(3) 1.0867(3) 0.0660(7) Uani 1 1 d . . . . .
H17 H 1.032685 0.383947 1.154477 0.079 Uiso 1 1 calc R . . . .
C5 C 0.4817(4) 0.9520(3) 0.6916(3) 0.0716(8) Uani 1 1 d . . . . .
F2B F 0.9125(16) 0.6381(15) 0.3673(14) 0.131(6) Uani 0.367(17) 1 d D U . A 1
C14 C 1.0927(4) 0.0809(3) 0.8900(3) 0.0729(8) Uani 1 1 d . . . . .
H14 H 1.107607 0.003071 0.824450 0.087 Uiso 1 1 calc R . . . .
F3B F 0.916(2) 0.8458(13) 0.441(2) 0.140(6) Uani 0.367(17) 1 d D U . A 1
C15 C 1.2098(4) 0.1515(4) 0.9838(4) 0.0818(9) Uani 1 1 d . . . . .
H15 H 1.305386 0.123180 0.980290 0.098 Uiso 1 1 calc R . . . .
C16 C 1.1879(4) 0.2633(4) 1.0828(4) 0.0830(9) Uani 1 1 d . . . . .
H16 H 1.267836 0.309415 1.147675 0.100 Uiso 1 1 calc R . . . .
C1 C 0.8976(3) 0.7328(3) 0.4774(3) 0.0756(8) Uani 1 1 d D U . . .
F2A F 0.8824(10) 0.7025(15) 0.3466(5) 0.152(4) Uani 0.633(17) 1 d D U . A 2
F3A F 0.9614(9) 0.8577(5) 0.5272(14) 0.141(4) Uani 0.633(17) 1 d D U . A 2
F1A F 0.9934(6) 0.6575(8) 0.5192(10) 0.117(3) Uani 0.633(17) 1 d D U . A 2
H3 H 0.705(4) 0.283(5) 1.249(4) 0.143(18) Uiso 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9882(14) . ?
Cu1 O1 1.9883(14) 2_666 ?
Cu1 O2 2.3376(14) . ?
Cu1 O2 2.3376(14) 2_666 ?
Cu1 N1 2.0085(16) 2_666 ?
Cu1 N1 2.0085(16) . ?
O1 C2 1.255(3) . ?
O2 C4 1.241(3) . ?
N1 C6 1.354(2) . ?
N1 C10 1.339(3) . ?
O3 N2 1.386(2) . ?
F6 C5 1.307(4) . ?
F5 C5 1.336(4) . ?
N2 C11 1.289(3) . ?
C6 C7 1.368(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.399(3) . ?
C8 C11 1.486(3) . ?
C9 C10 1.369(3) . ?
C12 C11 1.491(3) . ?
C12 C13 1.381(3) . ?
C12 C17 1.385(3) . ?
C2 C3 1.373(3) . ?
C2 C1 1.525(3) . ?
F4 C5 1.310(4) . ?
C4 C3 1.400(3) . ?
C4 C5 1.537(3) . ?
F1B C1 1.299(5) . ?
C13 C14 1.384(4) . ?
C17 C16 1.380(4) . ?
F2B C1 1.317(5) . ?
C14 C15 1.365(5) . ?
F3B C1 1.309(4) . ?
C15 C16 1.365(5) . ?
C1 F2A 1.296(4) . ?
C1 F3A 1.308(4) . ?
C1 F1A 1.298(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 2_666 ?
O1 Cu1 O2 84.90(6) . . ?
O1 Cu1 O2 95.10(6) 2_666 . ?
O1 Cu1 O2 95.10(6) . 2_666 ?
O1 Cu1 O2 84.90(6) 2_666 2_666 ?
O1 Cu1 N1 90.44(6) . 2_666 ?
O1 Cu1 N1 89.56(6) . . ?
O1 Cu1 N1 89.56(6) 2_666 2_666 ?
O1 Cu1 N1 90.44(6) 2_666 . ?
O2 Cu1 O2 180.00(7) 2_666 . ?
N1 Cu1 O2 86.81(6) 2_666 . ?
N1 Cu1 O2 93.19(6) . . ?
N1 Cu1 O2 93.19(6) 2_666 2_666 ?
N1 Cu1 O2 86.81(6) . 2_666 ?
N1 Cu1 N1 180.00(9) 2_666 . ?
C2 O1 Cu1 127.74(13) . . ?
C4 O2 Cu1 118.65(13) . . ?
C6 N1 Cu1 123.27(14) . . ?
C10 N1 Cu1 119.64(13) . . ?
C10 N1 C6 117.07(17) . . ?
C11 N2 O3 112.46(19) . . ?
N1 C6 C7 123.06(18) . . ?
C6 C7 C8 120.08(18) . . ?
C7 C8 C9 116.35(18) . . ?
C7 C8 C11 122.24(17) . . ?
C9 C8 C11 121.38(18) . . ?
C10 C9 C8 120.32(18) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 C17 118.3(2) . . ?
C17 C12 C11 120.6(2) . . ?
N1 C10 C9 123.10(18) . . ?
O1 C2 C3 129.7(2) . . ?
O1 C2 C1 112.5(2) . . ?
C3 C2 C1 117.9(2) . . ?
N2 C11 C8 114.02(19) . . ?
N2 C11 C12 126.29(19) . . ?
C8 C11 C12 119.65(17) . . ?
O2 C4 C3 128.1(2) . . ?
O2 C4 C5 114.9(2) . . ?
C3 C4 C5 117.0(2) . . ?
C2 C3 C4 124.2(2) . . ?
C12 C13 C14 121.0(3) . . ?
C16 C17 C12 120.6(3) . . ?
F6 C5 F5 106.0(3) . . ?
F6 C5 F4 107.3(3) . . ?
F6 C5 C4 111.2(2) . . ?
F5 C5 C4 113.6(2) . . ?
F4 C5 F5 107.7(3) . . ?
F4 C5 C4 110.7(2) . . ?
C15 C14 C13 119.5(3) . . ?
C16 C15 C14 120.6(3) . . ?
C15 C16 C17 120.0(3) . . ?
F1B C1 C2 114.2(6) . . ?
F1B C1 F2B 103.9(8) . . ?
F1B C1 F3B 109.0(8) . . ?
F2B C1 C2 111.2(6) . . ?
F3B C1 C2 114.7(6) . . ?
F3B C1 F2B 102.7(7) . . ?
F2A C1 C2 110.1(4) . . ?
F2A C1 F3A 109.0(5) . . ?
F2A C1 F1A 108.5(6) . . ?
F3A C1 C2 113.8(4) . . ?
F1A C1 C2 110.7(4) . . ?
F1A C1 F3A 104.4(5) . . ?

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
_geom_hbond_publ_flag
O3 H3 O2 0.821(10) 2.047(13) 2.859(2) 170(5) 2_667 yes

_olex2_date_sample_data_collection 2019-07-22
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_5b
_database_code_depnum_ccdc_archive 'CCDC 1942729'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H28 Cu F6 N4 O6'
_chemical_formula_sum            'C34 H28 Cu F6 N4 O6'
_chemical_formula_weight         766.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.3647(2)
_cell_length_b                   9.6311(2)
_cell_length_c                   17.9637(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.920(2)
_cell_angle_gamma                90
_cell_volume                     1760.73(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11219
_cell_measurement_temperature    296
_cell_measurement_theta_max      31.3990
_cell_measurement_theta_min      3.5300
_shelx_estimated_absorpt_T_max   0.791
_shelx_estimated_absorpt_T_min   0.655
_exptl_absorpt_coefficient_mu    0.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78433
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             782
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            33584
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         3.270
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3572
_reflns_number_total             4050
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.285
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4050
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0329
_refine_ls_restrained_S_all      1.103
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0467P)²+0.4133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0897
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C1-F1A = C1-F3A = C1-F2A = C1-F2B = C1-F3B = C1-F1B
 1.32 with sigma of 0.005
 F1A-F3A \\sim F1A-F2A \\sim F3A-F2A \\sim F2B-F3B \\sim F2B-F1B \\sim F3B-F1B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F2B, F1B, F3B, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1A, F2A, F3A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F2B)=Sof(F3B)=Sof(F1B)=1-FVAR(1)
 Sof(F1A)=Sof(F3A)=Sof(F2A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C3(H3A), C6(H6), C7(H7), C13(H13), C14(H14), C15(H15),
 C17(H17), C16(H16)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.03756(9) Uani 1 2 d S T P . .
O1 O 0.45547(11) 0.32033(11) 0.53713(7) 0.0457(3) Uani 1 1 d . . . . .
O2 O 0.63343(11) 0.53844(13) 0.60994(7) 0.0507(3) Uani 1 1 d . . . . .
N1 N 0.65890(13) 0.40968(14) 0.45795(8) 0.0476(3) Uani 1 1 d . . . . .
O3 O 1.20393(14) 0.23230(16) 0.37913(10) 0.0737(4) Uani 1 1 d . . . . .
N2 N 1.09578(15) 0.29721(17) 0.39882(10) 0.0599(4) Uani 1 1 d . . . . .
C2 C 0.49500(15) 0.27426(15) 0.60340(10) 0.0449(4) Uani 1 1 d . . . . .
F1A F 0.3016(3) 0.1492(6) 0.5992(4) 0.0928(16) Uani 0.563(14) 1 d D U . A 1
C10 C 0.65941(17) 0.27545(17) 0.43937(10) 0.0506(4) Uani 1 1 d . . . . .
H10 H 0.585247 0.222812 0.442157 0.061 Uiso 1 1 calc R . . . .
C11 C 0.99308(16) 0.21878(18) 0.38987(9) 0.0475(4) Uani 1 1 d . . . . .
F3A F 0.4535(8) 0.0802(9) 0.6822(3) 0.128(3) Uani 0.563(14) 1 d D U . A 1
C8 C 0.87617(15) 0.28595(17) 0.41095(9) 0.0445(3) Uani 1 1 d . . . . .
C9 C 0.76376(17) 0.21045(17) 0.41627(10) 0.0493(4) Uani 1 1 d . . . . .
H9 H 0.758994 0.116417 0.404281 0.059 Uiso 1 1 calc R . . . .
C3 C 0.58218(18) 0.32675(19) 0.66311(11) 0.0560(4) Uani 1 1 d . . . . .
H3A H 0.598176 0.274448 0.707419 0.067 Uiso 1 1 calc R . . . .
C4 C 0.65098(16) 0.45489(19) 0.66350(10) 0.0483(4) Uani 1 1 d . . . . .
C6 C 0.76659(18) 0.48346(17) 0.45159(12) 0.0550(4) Uani 1 1 d . . . . .
H6 H 0.768477 0.577438 0.463644 0.066 Uiso 1 1 calc R . . . .
C7 C 0.87341(17) 0.42706(18) 0.42828(11) 0.0562(4) Uani 1 1 d . . . . .
H7 H 0.944669 0.483125 0.423952 0.067 Uiso 1 1 calc R . . . .
C13 C 0.9031(2) 0.0371(2) 0.29535(11) 0.0612(5) Uani 1 1 d . . . . .
H13 H 0.851166 0.104856 0.267386 0.073 Uiso 1 1 calc R . . . .
C12 C 0.98676(16) 0.07273(18) 0.36243(9) 0.0481(4) Uani 1 1 d . . . . .
C1 C 0.4303(2) 0.1348(2) 0.61451(12) 0.0711(6) Uani 1 1 d D U . . .
C14 C 0.8966(2) -0.0987(3) 0.26996(14) 0.0794(7) Uani 1 1 d . . . . .
H14 H 0.841275 -0.121463 0.224565 0.095 Uiso 1 1 calc R . . . .
C5 C 0.7498(3) 0.4904(3) 0.73326(14) 0.0792(7) Uani 1 1 d . . . . .
H5A H 0.834070 0.505124 0.719821 0.119 Uiso 1 1 calc GR . . . .
H5B H 0.755646 0.415456 0.768962 0.119 Uiso 1 1 calc GR . . . .
H5C H 0.722831 0.573453 0.755645 0.119 Uiso 1 1 calc GR . . . .
F2A F 0.4527(12) 0.0401(7) 0.5657(7) 0.151(4) Uani 0.563(14) 1 d D U . A 1
C15 C 0.9707(3) -0.1995(3) 0.31089(17) 0.0888(8) Uani 1 1 d . . . . .
H15 H 0.965473 -0.290784 0.293670 0.107 Uiso 1 1 calc R . . . .
C17 C 1.0623(2) -0.0307(2) 0.40320(13) 0.0675(5) Uani 1 1 d . . . . .
H17 H 1.119437 -0.008590 0.448071 0.081 Uiso 1 1 calc R . . . .
C16 C 1.0532(3) -0.1656(3) 0.37770(16) 0.0880(7) Uani 1 1 d . . . . .
H16 H 1.103189 -0.234465 0.405873 0.106 Uiso 1 1 calc R . . . .
H3 H 1.257(3) 0.297(3) 0.3846(14) 0.085(8) Uiso 1 1 d . . . . .
F2B F 0.5096(9) 0.0351(7) 0.6013(7) 0.130(3) Uani 0.437(14) 1 d D U . A 2
F3B F 0.4244(11) 0.1134(11) 0.6864(3) 0.108(3) Uani 0.437(14) 1 d D U . A 2
F1B F 0.3164(9) 0.1178(12) 0.5731(7) 0.159(4) Uani 0.437(14) 1 d D U . 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 O1 1.9413(10) . ?
Cu1 O1 1.9414(10) 3_666 ?
Cu1 O2 2.2170(12) . ?
Cu1 O2 2.2170(12) 3_666 ?
Cu1 N1 2.1240(14) 3_666 ?
Cu1 N1 2.1240(14) . ?
O1 C2 1.264(2) . ?
O2 C4 1.241(2) . ?
N1 C10 1.335(2) . ?
N1 C6 1.346(2) . ?
O3 N2 1.387(2) . ?
N2 C11 1.290(2) . ?
C2 C3 1.362(2) . ?
C2 C1 1.531(2) . ?
F1A C1 1.317(3) . ?
C10 C9 1.380(2) . ?
C11 C8 1.485(2) . ?
C11 C12 1.488(2) . ?
F3A C1 1.304(4) . ?
C8 C9 1.392(2) . ?
C8 C7 1.396(2) . ?
C3 C4 1.425(2) . ?
C4 C5 1.500(3) . ?
C6 C7 1.368(3) . ?
C13 C12 1.388(2) . ?
C13 C14 1.383(3) . ?
C12 C17 1.387(3) . ?
C1 F2A 1.316(4) . ?
C1 F2B 1.314(4) . ?
C1 F3B 1.320(4) . ?
C1 F1B 1.281(4) . ?
C14 C15 1.364(4) . ?
C15 C16 1.374(4) . ?
C17 C16 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 O2 90.48(5) 3_666 . ?
O1 Cu1 O2 90.48(5) . 3_666 ?
O1 Cu1 O2 89.52(5) 3_666 3_666 ?
O1 Cu1 O2 89.52(5) . . ?
O1 Cu1 N1 89.54(5) . 3_666 ?
O1 Cu1 N1 90.46(5) 3_666 3_666 ?
O1 Cu1 N1 90.46(5) . . ?
O1 Cu1 N1 89.54(5) 3_666 . ?
O2 Cu1 O2 180.00(5) 3_666 . ?
N1 Cu1 O2 89.45(5) 3_666 3_666 ?
N1 Cu1 O2 89.45(5) . . ?
N1 Cu1 O2 90.55(5) . 3_666 ?
N1 Cu1 O2 90.55(5) 3_666 . ?
N1 Cu1 N1 180.0 3_666 . ?
C2 O1 Cu1 125.51(10) . . ?
C4 O2 Cu1 123.88(11) . . ?
C10 N1 Cu1 121.69(11) . . ?
C10 N1 C6 116.57(15) . . ?
C6 N1 Cu1 121.68(12) . . ?
C11 N2 O3 113.07(15) . . ?
O1 C2 C3 131.28(14) . . ?
O1 C2 C1 111.04(14) . . ?
C3 C2 C1 117.68(16) . . ?
N1 C10 C9 123.70(14) . . ?
N2 C11 C8 114.01(15) . . ?
N2 C11 C12 125.34(17) . . ?
C8 C11 C12 120.64(13) . . ?
C9 C8 C11 121.61(15) . . ?
C9 C8 C7 116.14(16) . . ?
C7 C8 C11 122.24(14) . . ?
C10 C9 C8 119.84(15) . . ?
C2 C3 C4 125.61(16) . . ?
O2 C4 C3 123.93(16) . . ?
O2 C4 C5 118.45(17) . . ?
C3 C4 C5 117.63(17) . . ?
N1 C6 C7 123.26(15) . . ?
C6 C7 C8 120.46(15) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C12 C11 120.15(17) . . ?
C17 C12 C11 121.26(16) . . ?
C17 C12 C13 118.59(18) . . ?
F1A C1 C2 109.4(3) . . ?
F3A C1 C2 117.9(4) . . ?
F3A C1 F1A 103.8(4) . . ?
F3A C1 F2A 108.5(6) . . ?
F2A C1 C2 112.6(3) . . ?
F2A C1 F1A 103.5(5) . . ?
F2B C1 C2 108.3(5) . . ?
F2B C1 F3B 102.1(6) . . ?
F3B C1 C2 111.5(4) . . ?
F1B C1 C2 114.5(4) . . ?
F1B C1 F2B 109.9(6) . . ?
F1B C1 F3B 109.8(7) . . ?
C15 C14 C13 120.6(2) . . ?
C14 C15 C16 119.7(2) . . ?
C16 C17 C12 120.4(2) . . ?
C15 C16 C17 120.5(2) . . ?

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
_geom_hbond_publ_flag
O3 H3 O2 0.82(3) 1.94(3) 2.7623(18) 173(3) 3_766 yes

_olex2_date_sample_data_collection 2017-11-19
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5a-II
_database_code_depnum_ccdc_archive 'CCDC 1942728'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C34 H22 Cu F12 N4 O6'
_chemical_formula_sum            'C34 H22 Cu F12 N4 O6'
_chemical_formula_weight         874.09
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.3294(5)
_cell_length_b                   22.7479(6)
_cell_length_c                   7.3599(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.836(4)
_cell_angle_gamma                90
_cell_volume                     1841.76(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3317
_cell_measurement_temperature    296
_cell_measurement_theta_max      29.5670
_cell_measurement_theta_min      3.4860
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.811
_exptl_absorpt_coefficient_mu    0.703
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.80142
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             878
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8821
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         3.136
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2879
_reflns_number_total             3611
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     299
_refine_ls_number_reflns         3611
_refine_ls_number_restraints     57
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0431
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.4885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 C5-F4A = C5-F4B = C5-F5A = C5-F5B = C5-F6A = C5-F6B
 1.32 with sigma of 0.005
 F4A-F5A \\sim F4A-F6A \\sim F5A-F6A \\sim F4B-F5B \\sim F4B-F6B \\sim F5B-F6B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F5B, F6B, F4B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4A, F5A, F6A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(O3B)=Sof(H3B)=1-FVAR(1)
 Sof(O3A)=Sof(H3A)=FVAR(1)
 Sof(F6B)=Sof(F4B)=Sof(F5B)=1-FVAR(2)
 Sof(F4A)=Sof(F6A)=Sof(F5A)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C7(H7), C6(H6), C3(H3), C17(H17), C13(H13), C15(H15),
 C16(H16), C14(H14)
5.b Idealised tetrahedral OH refined as rotating group:
 O3A(H3A), O3B(H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.04720(15) Uani 1 2 d S T P . .
O1 O 0.40324(16) 0.44279(7) 0.6216(3) 0.0619(5) Uani 1 1 d . . . . .
O2 O 0.55688(17) 0.42237(8) 0.3575(2) 0.0630(5) Uani 1 1 d . . . . .
N1 N 0.35257(18) 0.51312(8) 0.2870(3) 0.0499(5) Uani 1 1 d . . . . .
F3 F 0.3705(2) 0.30297(8) 0.7962(3) 0.1069(7) Uani 1 1 d . . . . .
N2 N 0.04158(19) 0.53938(10) -0.3239(3) 0.0617(6) Uani 1 1 d . . . . .
F2 F 0.3986(2) 0.38228(11) 0.9460(3) 0.1270(9) Uani 1 1 d . . . . .
F1 F 0.24088(19) 0.37058(11) 0.7303(4) 0.1301(9) Uani 1 1 d . . . . .
C8 C 0.1648(2) 0.54766(10) -0.0151(3) 0.0510(6) Uani 1 1 d . . . . .
C10 C 0.2470(2) 0.53304(11) 0.3128(3) 0.0545(6) Uani 1 1 d . . . . .
H10 H 0.236385 0.534836 0.434086 0.065 Uiso 1 1 calc R . . . .
C9 C 0.1530(2) 0.55110(12) 0.1674(3) 0.0565(6) Uani 1 1 d . . . . .
H9 H 0.081635 0.565592 0.192076 0.068 Uiso 1 1 calc R . . . .
C12 C 0.0028(2) 0.62431(12) -0.1445(3) 0.0572(6) Uani 1 1 d . . . . .
C7 C 0.2727(2) 0.52452(13) -0.0417(3) 0.0635(7) Uani 1 1 d . . . . .
H7 H 0.284140 0.520245 -0.161968 0.076 Uiso 1 1 calc R . . . .
C2 C 0.4219(2) 0.38832(11) 0.6391(3) 0.0554(6) Uani 1 1 d . . . . .
C4 C 0.5542(2) 0.37238(11) 0.4236(4) 0.0593(6) Uani 1 1 d . . . . .
C11 C 0.0667(2) 0.56950(11) -0.1731(3) 0.0559(6) Uani 1 1 d . . . . .
C6 C 0.3626(3) 0.50793(12) 0.1106(4) 0.0639(7) Uani 1 1 d . . . . .
H6 H 0.434039 0.492297 0.089632 0.077 Uiso 1 1 calc R . . . .
C3 C 0.4915(2) 0.35291(11) 0.5539(4) 0.0662(7) Uani 1 1 d . . . . .
H3 H 0.496969 0.313250 0.585461 0.079 Uiso 1 1 calc R . . . .
C17 C 0.0683(3) 0.67100(13) -0.0501(4) 0.0739(8) Uani 1 1 d . . . . .
H17 H 0.152412 0.668231 -0.010139 0.089 Uiso 1 1 calc R . . . .
C13 C -0.1225(3) 0.62976(15) -0.2042(4) 0.0770(8) Uani 1 1 d . . . . .
H13 H -0.168327 0.599263 -0.269925 0.092 Uiso 1 1 calc R . . . .
C1 C 0.3572(3) 0.36048(13) 0.7779(4) 0.0706(7) Uani 1 1 d . . . . .
O3A O -0.0473(3) 0.56542(17) -0.4742(4) 0.0851(13) Uani 0.638(5) 1 d . . . A 1
H3A H -0.061319 0.543131 -0.564372 0.128 Uiso 0.638(5) 1 calc GR . . A 1
C15 C -0.1128(4) 0.72596(18) -0.0735(5) 0.0999(12) Uani 1 1 d . . . . .
H15 H -0.151852 0.760166 -0.050548 0.120 Uiso 1 1 calc R . . . .
C16 C 0.0104(4) 0.72174(16) -0.0143(5) 0.0944(11) Uani 1 1 d . . . . .
H16 H 0.055310 0.752775 0.049776 0.113 Uiso 1 1 calc R . . . .
C14 C -0.1793(3) 0.68053(18) -0.1660(5) 0.0980(11) Uani 1 1 d . . . . .
H14 H -0.263510 0.683641 -0.203725 0.118 Uiso 1 1 calc R . . . .
C5 C 0.6331(3) 0.32751(13) 0.3543(5) 0.0918(10) Uani 1 1 d D U . . .
O3B O 0.1013(6) 0.4833(3) -0.3216(9) 0.083(2) Uani 0.362(5) 1 d . . . A 2
H3B H 0.081876 0.468443 -0.425988 0.125 Uiso 0.362(5) 1 calc GR . . A 2
F4A F 0.5923(14) 0.3131(7) 0.1791(10) 0.210(9) Uani 0.475(16) 1 d D U . B 1
F6A F 0.7431(6) 0.3482(3) 0.3635(18) 0.130(5) Uani 0.475(16) 1 d D U . B 1
F5A F 0.6495(11) 0.2774(3) 0.4408(17) 0.135(5) Uani 0.475(16) 1 d D U . B 1
F6B F 0.6606(10) 0.3439(3) 0.2001(12) 0.137(4) Uani 0.525(16) 1 d D U . B 2
F4B F 0.5751(11) 0.2787(3) 0.3032(19) 0.167(6) Uani 0.525(16) 1 d D U . B 2
F5B F 0.7298(9) 0.3167(6) 0.4882(13) 0.208(8) Uani 0.525(16) 1 d D U . 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
Cu1 O1 2.0410(17) . ?
Cu1 O1 2.0410(17) 3_666 ?
Cu1 O2 2.2264(17) . ?
Cu1 O2 2.2264(17) 3_666 ?
Cu1 N1 2.021(2) 3_666 ?
Cu1 N1 2.021(2) . ?
O1 C2 1.258(3) . ?
O2 C4 1.240(3) . ?
N1 C10 1.334(3) . ?
N1 C6 1.335(3) . ?
F3 C1 1.320(3) . ?
N2 C11 1.277(3) . ?
N2 O3A 1.434(3) . ?
N2 O3B 1.442(6) . ?
F2 C1 1.311(3) . ?
F1 C1 1.300(3) . ?
C8 C9 1.383(3) . ?
C8 C7 1.387(3) . ?
C8 C11 1.488(3) . ?
C10 C9 1.380(3) . ?
C12 C11 1.482(4) . ?
C12 C17 1.384(4) . ?
C12 C13 1.388(4) . ?
C7 C6 1.375(4) . ?
C2 C3 1.378(4) . ?
C2 C1 1.530(4) . ?
C4 C3 1.395(4) . ?
C4 C5 1.523(4) . ?
C17 C16 1.384(4) . ?
C13 C14 1.383(5) . ?
C15 C16 1.363(5) . ?
C15 C14 1.361(5) . ?
C5 F4A 1.303(4) . ?
C5 F6A 1.320(4) . ?
C5 F5A 1.298(4) . ?
C5 F6B 1.301(4) . ?
C5 F4B 1.299(4) . ?
C5 F5B 1.310(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 O2 86.97(7) . . ?
O1 Cu1 O2 86.97(7) 3_666 3_666 ?
O1 Cu1 O2 93.03(7) 3_666 . ?
O1 Cu1 O2 93.03(7) . 3_666 ?
O2 Cu1 O2 180.0 3_666 . ?
N1 Cu1 O1 89.80(8) 3_666 . ?
N1 Cu1 O1 90.20(8) . . ?
N1 Cu1 O1 89.80(8) . 3_666 ?
N1 Cu1 O1 90.20(8) 3_666 3_666 ?
N1 Cu1 O2 88.26(7) 3_666 . ?
N1 Cu1 O2 88.26(7) . 3_666 ?
N1 Cu1 O2 91.74(7) . . ?
N1 Cu1 O2 91.74(7) 3_666 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
C2 O1 Cu1 125.32(16) . . ?
C4 O2 Cu1 120.37(17) . . ?
C10 N1 Cu1 122.83(16) . . ?
C10 N1 C6 117.1(2) . . ?
C6 N1 Cu1 119.64(17) . . ?
C11 N2 O3A 114.7(2) . . ?
C11 N2 O3B 117.2(3) . . ?
C9 C8 C7 116.8(2) . . ?
C9 C8 C11 120.8(2) . . ?
C7 C8 C11 122.3(2) . . ?
N1 C10 C9 122.9(2) . . ?
C10 C9 C8 120.0(2) . . ?
C17 C12 C11 119.7(2) . . ?
C17 C12 C13 118.4(3) . . ?
C13 C12 C11 121.9(3) . . ?
C6 C7 C8 119.7(2) . . ?
O1 C2 C3 129.0(2) . . ?
O1 C2 C1 112.4(2) . . ?
C3 C2 C1 118.6(2) . . ?
O2 C4 C3 128.7(2) . . ?
O2 C4 C5 114.3(2) . . ?
C3 C4 C5 117.0(2) . . ?
N2 C11 C8 118.0(2) . . ?
N2 C11 C12 124.0(2) . . ?
C12 C11 C8 117.9(2) . . ?
N1 C6 C7 123.3(2) . . ?
C2 C3 C4 124.6(2) . . ?
C16 C17 C12 121.0(3) . . ?
C14 C13 C12 120.1(3) . . ?
F3 C1 C2 114.6(3) . . ?
F2 C1 F3 105.8(3) . . ?
F2 C1 C2 110.6(2) . . ?
F1 C1 F3 106.7(2) . . ?
F1 C1 F2 107.4(3) . . ?
F1 C1 C2 111.3(2) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C17 119.6(3) . . ?
C15 C14 C13 120.4(3) . . ?
F4A C5 C4 113.7(5) . . ?
F4A C5 F6A 104.3(8) . . ?
F6A C5 C4 111.5(4) . . ?
F5A C5 C4 116.8(4) . . ?
F5A C5 F4A 103.9(6) . . ?
F5A C5 F6A 105.4(6) . . ?
F6B C5 C4 112.4(4) . . ?
F6B C5 F5B 112.2(7) . . ?
F4B C5 C4 111.9(5) . . ?
F4B C5 F6B 101.7(5) . . ?
F4B C5 F5B 109.4(7) . . ?
F5B C5 C4 109.0(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3A H3A N2 0.82 2.08 2.818(4) 149.2 3_564 yes
O3B H3B N2 0.82 2.04 2.771(6) 148.9 3_564 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1942725'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H18 Cu F12 N4 O6'
_chemical_formula_sum            'C24 H18 Cu F12 N4 O6'
_chemical_formula_weight         749.96
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.7979(6)
_cell_length_b                   10.8757(6)
_cell_length_c                   11.5285(8)
_cell_angle_alpha                117.344(6)
_cell_angle_beta                 90.254(7)
_cell_angle_gamma                98.312(6)
_cell_volume                     746.70(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1141
_cell_measurement_temperature    296
_cell_measurement_theta_max      24.1450
_cell_measurement_theta_min      3.8680
_shelx_estimated_absorpt_T_max   0.755
_shelx_estimated_absorpt_T_min   0.652
_exptl_absorpt_coefficient_mu    0.852
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.668
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             375
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5527
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.546
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2054
_reflns_number_total             2604
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2604
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1078
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.81 with sigma of 0.01
 C5-F6A = C5-F4A = C5-F5A = C5-F5B = C5-F6B = C5-F4B
 1.32 with sigma of 0.01
 F6A-F4A \\sim F6A-F5A \\sim F4A-F5A \\sim F5B-F6B \\sim F5B-F4B \\sim F6B-F4B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F4A, F5A, F6A, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5B, F6B, F4B, C5
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F5B)=Sof(F6B)=Sof(F4B)=1-FVAR(1)
 Sof(F6A)=Sof(F4A)=Sof(F5A)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C9(H9), C10(H10), C3(H3A)
5.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.0457(2) Uani 1 2 d S T P . .
O1 O 0.3543(3) 0.6210(2) 0.6533(2) 0.0539(6) Uani 1 1 d . . . . .
O2 O 0.6649(3) 0.4552(2) 0.6439(2) 0.0572(6) Uani 1 1 d . . . . .
N1 N 0.2861(4) 0.3291(2) 0.4588(2) 0.0452(6) Uani 1 1 d . . . . .
F2 F 0.2795(5) 0.7956(3) 0.9850(2) 0.1166(10) Uani 1 1 d . . . . .
F1 F 0.0792(4) 0.7376(3) 0.8185(3) 0.1114(9) Uani 1 1 d . . . . .
F3 F 0.3372(5) 0.8885(2) 0.8580(3) 0.1150(10) Uani 1 1 d . . . . .
O3 O -0.4722(4) -0.1317(3) 0.3633(3) 0.0847(9) Uani 1 1 d D . . . .
N2 N -0.3247(4) -0.0118(3) 0.4120(3) 0.0624(8) Uani 1 1 d . . . . .
F6A F 0.8293(13) 0.5740(8) 0.9594(6) 0.098(3) Uani 0.644(16) 1 d D U . A 1
C2 C 0.3889(5) 0.6556(3) 0.7727(3) 0.0525(8) Uani 1 1 d . . . . .
C4 C 0.6428(5) 0.5120(3) 0.7625(3) 0.0521(8) Uani 1 1 d . . . . .
C6 C 0.1021(5) 0.3416(3) 0.4978(3) 0.0518(8) Uani 1 1 d . . . . .
H6 H 0.075702 0.431393 0.551582 0.062 Uiso 1 1 calc R . . . .
C11 C -0.1794(5) -0.0273(3) 0.3400(3) 0.0559(8) Uani 1 1 d . . . . .
C8 C -0.0170(5) 0.0951(3) 0.3837(3) 0.0473(7) Uani 1 1 d . . . . .
C7 C -0.0500(5) 0.2314(3) 0.4640(3) 0.0526(8) Uani 1 1 d . . . . .
H7 H -0.175035 0.247340 0.494407 0.063 Uiso 1 1 calc R . . . .
C9 C 0.1741(5) 0.0811(3) 0.3448(3) 0.0610(9) Uani 1 1 d . . . . .
H9 H 0.204361 -0.007527 0.291183 0.073 Uiso 1 1 calc R . . . .
C10 C 0.3194(5) 0.1973(3) 0.3850(3) 0.0587(9) Uani 1 1 d . . . . .
H10 H 0.447609 0.184034 0.359774 0.070 Uiso 1 1 calc R . . . .
C5 C 0.7699(6) 0.4698(4) 0.8443(3) 0.0701(10) Uani 1 1 d D U . . .
C3 C 0.5169(6) 0.6093(4) 0.8306(3) 0.0647(10) Uani 1 1 d . . . . .
H3A H 0.520373 0.644722 0.921079 0.078 Uiso 1 1 calc R . . . .
C1 C 0.2712(7) 0.7699(4) 0.8613(4) 0.0748(11) Uani 1 1 d . . . . .
F4A F 0.6785(17) 0.3710(10) 0.8644(11) 0.152(4) Uani 0.644(16) 1 d D U . A 1
F5A F 0.9409(15) 0.4357(16) 0.7915(7) 0.132(4) Uani 0.644(16) 1 d D U . A 1
C12 C -0.1691(7) -0.1594(4) 0.2163(4) 0.1026(16) Uani 1 1 d . . . . .
H12A H -0.132038 -0.228831 0.237780 0.154 Uiso 1 1 calc GR . . . .
H12B H -0.071569 -0.139934 0.164444 0.154 Uiso 1 1 calc GR . . . .
H12C H -0.297186 -0.193831 0.167630 0.154 Uiso 1 1 calc GR . . . .
H3 H -0.547(5) -0.100(4) 0.421(3) 0.103(17) Uiso 1 1 d D . . . .
F5B F 0.830(3) 0.3505(11) 0.7737(9) 0.090(4) Uani 0.356(16) 1 d D U . A 2
F6B F 0.910(3) 0.5637(17) 0.920(2) 0.151(9) Uani 0.356(16) 1 d D U . A 2
F4B F 0.655(3) 0.435(2) 0.921(2) 0.140(7) Uani 0.356(16) 1 d D U . 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 O1 2.023(2) 2_666 ?
Cu1 O1 2.023(2) . ?
Cu1 O2 2.266(2) . ?
Cu1 O2 2.266(2) 2_666 ?
Cu1 N1 2.049(2) . ?
Cu1 N1 2.049(2) 2_666 ?
O1 C2 1.260(4) . ?
O2 C4 1.235(3) . ?
N1 C6 1.335(4) . ?
N1 C10 1.344(4) . ?
F2 C1 1.320(4) . ?
F1 C1 1.331(5) . ?
F3 C1 1.321(5) . ?
O3 N2 1.402(4) . ?
O3 H3 0.817(10) . ?
N2 C11 1.273(4) . ?
F6A C5 1.300(6) . ?
C2 C3 1.373(5) . ?
C2 C1 1.535(5) . ?
C4 C5 1.533(5) . ?
C4 C3 1.404(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.366(4) . ?
C11 C8 1.483(4) . ?
C11 C12 1.499(5) . ?
C8 C7 1.394(4) . ?
C8 C9 1.383(4) . ?
C7 H7 0.9300 . ?
C9 H9 0.9300 . ?
C9 C10 1.372(4) . ?
C10 H10 0.9300 . ?
C5 F4A 1.277(7) . ?
C5 F5A 1.335(6) . ?
C5 F5B 1.303(7) . ?
C5 F6B 1.268(9) . ?
C5 F4B 1.331(8) . ?
C3 H3A 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(10) 2_666 . ?
O1 Cu1 O2 93.61(8) 2_666 . ?
O1 Cu1 O2 86.39(8) . . ?
O1 Cu1 O2 86.39(8) 2_666 2_666 ?
O1 Cu1 O2 93.61(8) . 2_666 ?
O1 Cu1 N1 89.59(9) 2_666 . ?
O1 Cu1 N1 90.41(9) 2_666 2_666 ?
O1 Cu1 N1 89.59(9) . 2_666 ?
O1 Cu1 N1 90.41(9) . . ?
O2 Cu1 O2 180.0 2_666 . ?
N1 Cu1 O2 90.13(9) 2_666 . ?
N1 Cu1 O2 89.87(9) 2_666 2_666 ?
N1 Cu1 O2 90.13(9) . 2_666 ?
N1 Cu1 O2 89.87(9) . . ?
N1 Cu1 N1 180.0 . 2_666 ?
C2 O1 Cu1 128.0(2) . . ?
C4 O2 Cu1 122.8(2) . . ?
C6 N1 Cu1 122.2(2) . . ?
C6 N1 C10 115.8(3) . . ?
C10 N1 Cu1 121.9(2) . . ?
N2 O3 H3 97(3) . . ?
C11 N2 O3 112.5(3) . . ?
O1 C2 C3 129.5(3) . . ?
O1 C2 C1 112.1(3) . . ?
C3 C2 C1 118.4(3) . . ?
O2 C4 C5 115.1(3) . . ?
O2 C4 C3 128.3(3) . . ?
C3 C4 C5 116.7(3) . . ?
N1 C6 H6 117.8 . . ?
N1 C6 C7 124.4(3) . . ?
C7 C6 H6 117.8 . . ?
N2 C11 C8 116.2(3) . . ?
N2 C11 C12 123.4(3) . . ?
C8 C11 C12 120.4(3) . . ?
C7 C8 C11 121.7(3) . . ?
C9 C8 C11 122.1(3) . . ?
C9 C8 C7 116.2(3) . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
N1 C10 C9 123.4(3) . . ?
N1 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
F6A C5 C4 112.0(5) . . ?
F6A C5 F5A 103.0(6) . . ?
F4A C5 F6A 106.0(6) . . ?
F4A C5 C4 113.6(5) . . ?
F4A C5 F5A 109.9(6) . . ?
F5A C5 C4 111.6(4) . . ?
F5B C5 C4 112.4(5) . . ?
F5B C5 F4B 99.5(7) . . ?
F6B C5 C4 116.0(10) . . ?
F6B C5 F5B 112.2(10) . . ?
F6B C5 F4B 105.6(11) . . ?
F4B C5 C4 109.6(9) . . ?
C2 C3 C4 124.5(3) . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3A 117.8 . . ?
F2 C1 F1 107.1(4) . . ?
F2 C1 F3 108.0(3) . . ?
F2 C1 C2 114.5(3) . . ?
F1 C1 C2 111.5(3) . . ?
F3 C1 F1 105.4(4) . . ?
F3 C1 C2 109.9(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
_geom_hbond_publ_flag
O3 H3 N2 0.817(10) 2.026(14) 2.827(4) 167(4) 2_456 yes

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
####################################################################### 
# 
# 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_3b
_database_code_depnum_ccdc_archive 'CCDC 1942724'
loop_
_audit_author_name
_audit_author_address
'Marijana Dakovic'
;University of Zagreb
Croatia
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2019-09-30 downloaded from the CCDC.
;
_audit_creation_date             2019-07-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 Cu F6 N2 O5'
_chemical_formula_sum            'C16 H14 Cu F6 N2 O5'
_chemical_formula_weight         491.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.7411(3)
_cell_length_b                   15.9660(8)
_cell_length_c                   18.5837(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.453(3)
_cell_angle_gamma                90
_cell_volume                     1994.10(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2070
_cell_measurement_temperature    296
_cell_measurement_theta_max      26.0150
_cell_measurement_theta_min      3.5390
_shelx_estimated_absorpt_T_max   0.881
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    1.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.638
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             988
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            8392
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_temperature      296
_diffrn_detector_area_resol_mean 16.3426
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2790
_reflns_number_total             3705
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.841
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     333
_refine_ls_number_reflns         3705
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0495
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0878P)²+0.0384P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1340
_refine_ls_wR_factor_ref         0.1484
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O5-H5
 0.81 with sigma of 0.01
 C1-F3B = C1-F2A = C1-F3A = C1-F1B = C1-F1A = C1-F2B
 1.32 with sigma of 0.01
 C6-F6A = C6-F5A = C6-F4A = C6-F4B = C6-F6B = C6-F5B
 1.32 with sigma of 0.01
 F3B-F1B \\sim F3B-F2B \\sim F2A-F3A \\sim F2A-F1A \\sim F3A-F1A \\sim F1B-F2B
 with sigma of 0.04
 F6A-F5A \\sim F6A-F4A \\sim F5A-F4A \\sim F4B-F6B \\sim F4B-F5B \\sim F6B-F5B
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 F1A, F3A, F2A, C1
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F1B, C1, F2B, F3B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F6B, F5B, F4B, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F4A, F5A, F6A, C6
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Others
 Sof(F4B)=Sof(F6B)=Sof(F5B)=1-FVAR(1)
 Sof(F6A)=Sof(F5A)=Sof(F4A)=FVAR(1)
 Sof(F1B)=Sof(F3B)=Sof(F2B)=1-FVAR(2)
 Sof(F3A)=Sof(F1A)=Sof(F2A)=FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C12(H12), C11(H11), C14(H14), C15(H15), C16(H16), C3(H3), C8(H8)
5.b Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57019(6) 0.63502(3) 0.71778(2) 0.0480(2) Uani 1 1 d . . . . .
O1 O 0.3951(4) 0.64586(16) 0.79452(14) 0.0562(7) Uani 1 1 d . . . . .
O2 O 0.7192(4) 0.54268(16) 0.76681(13) 0.0563(6) Uani 1 1 d . . . . .
O3 O 0.3899(4) 0.70696(18) 0.65623(14) 0.0608(7) Uani 1 1 d . . . . .
O4 O 0.7047(4) 0.59878(18) 0.63517(13) 0.0624(7) Uani 1 1 d . . . . .
N1 N 0.7772(4) 0.73644(19) 0.75916(16) 0.0503(7) Uani 1 1 d . . . . .
F3A F 0.0772(12) 0.6276(12) 0.8716(9) 0.107(3) Uani 0.68(4) 1 d D U P A 1
O5 O 1.4175(5) 1.0235(2) 0.8217(3) 0.0974(11) Uani 1 1 d D . . . .
C13 C 1.0289(5) 0.8701(2) 0.8004(2) 0.0504(9) Uani 1 1 d . . . . .
N2 N 1.3224(5) 0.9509(2) 0.7947(2) 0.0727(10) Uani 1 1 d . . . . .
F1A F 0.286(2) 0.7056(7) 0.9297(11) 0.152(5) Uani 0.68(4) 1 d D U P A 1
C12 C 0.8405(6) 0.8627(2) 0.8260(2) 0.0573(10) Uani 1 1 d . . . . .
H12 H 0.796133 0.901945 0.858018 0.069 Uiso 1 1 calc R . . . .
C11 C 0.7214(5) 0.7966(2) 0.8031(2) 0.0549(9) Uani 1 1 d . . . . .
H11 H 0.594316 0.793634 0.819168 0.066 Uiso 1 1 calc R . . . .
C14 C 1.0881(5) 0.8074(3) 0.7557(2) 0.0587(10) Uani 1 1 d . . . . .
H14 H 1.213754 0.809231 0.738397 0.070 Uiso 1 1 calc R . . . .
C15 C 0.9607(5) 0.7421(2) 0.7368(2) 0.0606(10) Uani 1 1 d . . . . .
H15 H 1.004284 0.700112 0.707141 0.073 Uiso 1 1 calc R . . . .
C2 C 0.4114(6) 0.6037(3) 0.8519(2) 0.0578(10) Uani 1 1 d . . . . .
C7 C 0.4017(6) 0.7165(3) 0.5886(2) 0.0608(10) Uani 1 1 d . . . . .
F6A F 0.072(2) 0.7413(15) 0.5436(19) 0.237(13) Uani 0.40(2) 1 d D U P B 1
C4 C 0.6924(6) 0.5125(2) 0.8281(2) 0.0587(10) Uani 1 1 d . . . . .
C16 C 1.1572(6) 0.9417(2) 0.8208(2) 0.0576(10) Uani 1 1 d . . . . .
H16 H 1.115822 0.980798 0.853539 0.069 Uiso 1 1 calc R . . . .
F2A F 0.250(3) 0.5765(13) 0.9605(8) 0.154(5) Uani 0.68(4) 1 d D U P A 1
C9 C 0.6750(7) 0.6224(3) 0.5704(2) 0.0631(11) Uani 1 1 d . . . . .
C3 C 0.5441(7) 0.5407(3) 0.8714(2) 0.0681(11) Uani 1 1 d . . . . .
H3 H 0.535204 0.515289 0.916063 0.082 Uiso 1 1 calc R . . . .
C8 C 0.5310(6) 0.6808(3) 0.5458(2) 0.0717(12) Uani 1 1 d . . . . .
H8 H 0.523836 0.695964 0.497393 0.086 Uiso 1 1 calc R . . . .
C5 C 0.8250(8) 0.4421(3) 0.8544(2) 0.0822(14) Uani 1 1 d . . . . .
H5A H 0.755890 0.389895 0.846762 0.123 Uiso 1 1 calc GR . . . .
H5B H 0.861600 0.449217 0.905030 0.123 Uiso 1 1 calc GR . . . .
H5C H 0.942580 0.441974 0.828445 0.123 Uiso 1 1 calc GR . . . .
F5A F 0.217(3) 0.8438(9) 0.5916(9) 0.124(6) Uani 0.40(2) 1 d D U P B 1
F4A F 0.288(5) 0.804(2) 0.4903(10) 0.253(14) Uani 0.40(2) 1 d D U P B 1
C6 C 0.2464(7) 0.7763(3) 0.5539(3) 0.0835(13) Uani 1 1 d D U . . .
C1 C 0.2610(7) 0.6290(3) 0.9045(2) 0.0829(14) Uani 1 1 d D U . . .
C10 C 0.8095(9) 0.5831(4) 0.5187(2) 0.110(2) Uani 1 1 d . . . . .
H10A H 0.945398 0.588000 0.537892 0.165 Uiso 1 1 calc GR . . . .
H10B H 0.792730 0.611326 0.473043 0.165 Uiso 1 1 calc GR . . . .
H10C H 0.775966 0.525008 0.512318 0.165 Uiso 1 1 calc GR . . . .
H5 H 1.524(4) 1.025(4) 0.805(3) 0.10(2) Uiso 1 1 d D . . . .
F4B F 0.294(2) 0.8517(5) 0.5730(12) 0.187(8) Uani 0.60(2) 1 d D U P B 2
F6B F 0.227(2) 0.7693(13) 0.4835(4) 0.178(6) Uani 0.60(2) 1 d D U P B 2
F5B F 0.0699(8) 0.7602(7) 0.5726(6) 0.111(3) Uani 0.60(2) 1 d D U P B 2
F1B F 0.265(4) 0.7126(6) 0.9098(10) 0.091(5) Uani 0.32(4) 1 d D U P A 2
F3B F 0.074(3) 0.609(3) 0.887(2) 0.124(9) Uani 0.32(4) 1 d D U P A 2
F2B F 0.317(4) 0.6063(16) 0.9717(7) 0.098(6) Uani 0.32(4) 1 d D U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.928(3) . ?
Cu1 O2 1.968(2) . ?
Cu1 O3 1.972(2) . ?
Cu1 O4 1.931(3) . ?
Cu1 N1 2.235(3) . ?
O1 C2 1.259(5) . ?
O2 C4 1.263(4) . ?
O3 C7 1.274(4) . ?
O4 C9 1.261(5) . ?
N1 C11 1.333(5) . ?
N1 C15 1.338(5) . ?
F3A C1 1.339(7) . ?
O5 N2 1.398(5) . ?
C13 C12 1.395(6) . ?
C13 C14 1.378(5) . ?
C13 C16 1.465(5) . ?
N2 C16 1.258(5) . ?
F1A C1 1.316(8) . ?
C12 C11 1.373(5) . ?
C14 C15 1.379(5) . ?
C2 C3 1.375(6) . ?
C2 C1 1.516(6) . ?
C7 C8 1.351(6) . ?
C7 C6 1.523(6) . ?
F6A C6 1.301(9) . ?
C4 C3 1.405(6) . ?
C4 C5 1.494(5) . ?
F2A C1 1.343(8) . ?
C9 C8 1.398(6) . ?
C9 C10 1.508(6) . ?
F5A C6 1.309(9) . ?
F4A C6 1.314(9) . ?
C6 F4B 1.289(8) . ?
C6 F6B 1.309(7) . ?
C6 F5B 1.291(7) . ?
C1 F1B 1.338(9) . ?
C1 F3B 1.316(10) . ?
C1 F2B 1.329(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 92.56(11) . . ?
O1 Cu1 O3 89.52(11) . . ?
O1 Cu1 O4 165.22(12) . . ?
O1 Cu1 N1 94.71(11) . . ?
O2 Cu1 O3 167.06(11) . . ?
O2 Cu1 N1 95.79(11) . . ?
O3 Cu1 N1 96.77(12) . . ?
O4 Cu1 O2 83.64(11) . . ?
O4 Cu1 O3 91.14(11) . . ?
O4 Cu1 N1 99.87(12) . . ?
C2 O1 Cu1 124.1(3) . . ?
C4 O2 Cu1 126.9(3) . . ?
C7 O3 Cu1 124.0(3) . . ?
C9 O4 Cu1 128.2(3) . . ?
C11 N1 Cu1 122.3(2) . . ?
C11 N1 C15 116.9(3) . . ?
C15 N1 Cu1 120.6(2) . . ?
C12 C13 C16 120.9(3) . . ?
C14 C13 C12 117.2(3) . . ?
C14 C13 C16 121.9(4) . . ?
C16 N2 O5 110.7(4) . . ?
C11 C12 C13 119.1(3) . . ?
N1 C11 C12 123.9(3) . . ?
C13 C14 C15 119.9(4) . . ?
N1 C15 C14 123.0(4) . . ?
O1 C2 C3 128.8(4) . . ?
O1 C2 C1 112.6(4) . . ?
C3 C2 C1 118.6(4) . . ?
O3 C7 C8 128.5(4) . . ?
O3 C7 C6 113.6(4) . . ?
C8 C7 C6 117.9(4) . . ?
O2 C4 C3 123.5(4) . . ?
O2 C4 C5 117.3(4) . . ?
C3 C4 C5 119.2(4) . . ?
N2 C16 C13 121.0(4) . . ?
O4 C9 C8 124.5(4) . . ?
O4 C9 C10 115.1(4) . . ?
C8 C9 C10 120.4(4) . . ?
C2 C3 C4 124.1(4) . . ?
C7 C8 C9 123.6(4) . . ?
F6A C6 C7 112.1(11) . . ?
F6A C6 F5A 105.2(13) . . ?
F6A C6 F4A 105.6(14) . . ?
F5A C6 C7 114.5(9) . . ?
F5A C6 F4A 104.5(13) . . ?
F4A C6 C7 114.0(12) . . ?
F4B C6 C7 108.6(7) . . ?
F4B C6 F6B 111.0(11) . . ?
F4B C6 F5B 109.1(9) . . ?
F6B C6 C7 112.6(7) . . ?
F5B C6 C7 112.3(5) . . ?
F5B C6 F6B 103.2(8) . . ?
F3A C1 C2 110.1(9) . . ?
F3A C1 F2A 103.8(9) . . ?
F1A C1 F3A 105.5(9) . . ?
F1A C1 C2 113.8(8) . . ?
F1A C1 F2A 108.5(8) . . ?
F2A C1 C2 114.3(7) . . ?
F1B C1 C2 107.6(11) . . ?
F3B C1 C2 116.7(19) . . ?
F3B C1 F1B 105.8(17) . . ?
F3B C1 F2B 111.7(14) . . ?
F2B C1 C2 112.1(12) . . ?
F2B C1 F1B 101.5(12) . . ?

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
_geom_hbond_publ_flag
O5 H5 O2 0.804(10) 2.284(17) 3.070(5) 166(5) 2_756 yes
O5 H5 O4 0.804(10) 2.37(5) 2.873(4) 121(5) 2_756 yes

