# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_cmpd1_CuTTAphenNO3
_database_code_depnum_ccdc_archive 'CCDC 2056492'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12 Cu F3 N3 O5 S'
_chemical_formula_sum            'C20 H12 Cu F3 N3 O5 S'
_chemical_formula_weight         526.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   7.6341(4)
_cell_length_b                   7.7048(4)
_cell_length_c                   9.5687(4)
_cell_angle_alpha                95.380(2)
_cell_angle_beta                 108.445(2)
_cell_angle_gamma                110.266(2)
_cell_volume                     487.61(4)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7182
_cell_measurement_theta_min      2.30
_cell_measurement_theta_max      28.75

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.794
_exptl_crystal_F_000             265
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.297
_shelx_estimated_absorpt_T_min   0.781
_shelx_estimated_absorpt_T_max   0.781
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            10769
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.305
_diffrn_reflns_theta_max         26.992
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.805
_diffrn_reflns_point_group_measured_fraction_full 0.831
_reflns_number_total             3411
_reflns_number_gt                3339
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.611
_reflns_Friedel_fraction_max     0.611
_reflns_Friedel_fraction_full    0.662

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

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0269P)²+0.1082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3411
_refine_ls_number_parameters     298
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0220
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0498
_refine_ls_wR_factor_gt          0.0494
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.21808(3) 0.22447(3) 0.32236(3) 0.01204(10) Uani 1 1 d . . . . .
S1 S 0.76371(12) 0.75790(12) 0.68051(9) 0.01783(19) Uani 1 1 d . . . . .
F1 F 0.1310(3) 0.7102(3) -0.0071(2) 0.0231(4) Uani 1 1 d . . . . .
F2 F 0.2036(3) 0.4906(3) -0.0993(2) 0.0235(4) Uani 1 1 d . . . . .
F3 F -0.0854(3) 0.4200(3) -0.0821(2) 0.0218(4) Uani 1 1 d . . . . .
O1 O 0.4157(4) 0.4701(3) 0.4442(3) 0.0149(5) Uani 1 1 d . . . . .
O2 O 0.1033(3) 0.3272(3) 0.1576(3) 0.0137(5) Uani 1 1 d . . . . .
O3 O 0.4434(3) 0.1419(4) 0.2619(2) 0.0207(5) Uani 1 1 d . . . . .
O4 O 0.5617(4) 0.0481(4) 0.1071(3) 0.0306(6) Uani 1 1 d . . . . .
O5 O 0.3363(4) 0.1638(4) 0.0280(3) 0.0231(5) Uani 1 1 d . . . . .
N1 N -0.0016(4) -0.0340(4) 0.2280(3) 0.0127(7) Uani 1 1 d . . . . .
N2 N 0.2858(4) 0.1059(4) 0.5004(3) 0.0134(6) Uani 1 1 d . . . . .
N3 N 0.4459(4) 0.1160(4) 0.1300(3) 0.0141(6) Uani 1 1 d . . . . .
C1 C 0.0136(5) -0.1592(5) 0.3174(4) 0.0115(6) Uani 1 1 d . . . . .
C2 C -0.1153(5) -0.3509(5) 0.2733(4) 0.0161(7) Uani 1 1 d . . . . .
C3 C -0.2687(5) -0.4136(5) 0.1287(4) 0.0176(7) Uani 1 1 d . . . . .
H3 H -0.3604 -0.5431 0.0929 0.021 Uiso 1 1 calc R U . . .
C4 C -0.2843(5) -0.2855(5) 0.0398(4) 0.0180(7) Uani 1 1 d . . . . .
H4 H -0.3885 -0.3258 -0.0575 0.022 Uiso 1 1 calc R U . . .
C5 C -0.1470(5) -0.0963(5) 0.0924(4) 0.0156(7) Uani 1 1 d . . . . .
H5 H -0.1583 -0.0098 0.0290 0.019 Uiso 1 1 calc R U . . .
C6 C 0.1701(5) -0.0821(5) 0.4651(4) 0.0125(7) Uani 1 1 d . . . . .
C7 C 0.1948(5) -0.2007(5) 0.5658(4) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.3458(5) -0.1139(5) 0.7103(4) 0.0187(7) Uani 1 1 d . . . . .
H8 H 0.3665 -0.1874 0.7835 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4633(5) 0.0764(5) 0.7458(4) 0.0195(7) Uani 1 1 d . . . . .
H9 H 0.5660 0.1357 0.8433 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4303(5) 0.1828(5) 0.6365(4) 0.0162(7) Uani 1 1 d . . . . .
H10 H 0.5142 0.3143 0.6608 0.019 Uiso 1 1 calc R U . . .
C11 C -0.0847(5) -0.4711(5) 0.3765(4) 0.0200(7) Uani 1 1 d . . . . .
H11 H -0.1689 -0.6029 0.3468 0.024 Uiso 1 1 calc R U . . .
C12 C 0.0641(5) -0.3980(5) 0.5167(4) 0.0207(7) Uani 1 1 d . . . . .
H12 H 0.0814 -0.4800 0.5833 0.025 Uiso 1 1 calc R U . . .
C13 C 0.9254(5) 0.9906(5) 0.7363(4) 0.0196(7) Uani 1 1 d . . . . .
H13 H 1.0315 1.0466 0.8326 0.024 Uiso 1 1 calc R U . . .
C14 C 0.8847(5) 1.0874(5) 0.6263(4) 0.0200(7) Uani 1 1 d . . . . .
H14 H 0.9598 1.2185 0.6372 0.024 Uiso 1 1 calc R U . . .
C15 C 0.7177(5) 0.9703(5) 0.4942(4) 0.0171(7) Uani 1 1 d . . . . .
H15 H 0.6683 1.0148 0.4068 0.021 Uiso 1 1 calc R U . . .
C16 C 0.6352(5) 0.7862(5) 0.5057(4) 0.0131(7) Uani 1 1 d . . . . .
C17 C 0.4642(5) 0.6228(5) 0.3985(4) 0.0125(7) Uani 1 1 d . . . . .
C18 C 0.3636(5) 0.6408(5) 0.2513(3) 0.0132(6) Uani 1 1 d . . . . .
H18 H 0.4139 0.7585 0.2242 0.016 Uiso 1 1 calc R U . . .
C19 C 0.1970(5) 0.4949(5) 0.1473(4) 0.0121(7) Uani 1 1 d . . . . .
C20 C 0.1101(5) 0.5302(5) -0.0108(4) 0.0149(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.927(2) . ?
Cu1 O2 1.929(2) . ?
Cu1 N1 1.996(3) . ?
Cu1 N2 2.017(3) . ?
Cu1 O3 2.241(2) . ?
S1 C13 1.701(4) . ?
S1 C16 1.728(3) . ?
F1 C20 1.336(4) . ?
F2 C20 1.343(4) . ?
F3 C20 1.336(4) . ?
O1 C17 1.269(4) . ?
O2 C19 1.272(4) . ?
O3 N3 1.266(3) . ?
O4 N3 1.234(3) . ?
O5 N3 1.246(3) . ?
N1 C5 1.323(5) . ?
N1 C1 1.358(4) . ?
N2 C10 1.325(4) . ?
N2 C6 1.351(5) . ?
C1 C2 1.393(5) . ?
C1 C6 1.435(5) . ?
C2 C3 1.406(5) . ?
C2 C11 1.436(4) . ?
C3 C4 1.373(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.396(5) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.403(4) . ?
C7 C8 1.404(5) . ?
C7 C12 1.430(5) . ?
C8 C9 1.368(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.403(4) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 C12 1.363(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.364(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.417(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.369(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.454(5) . ?
C17 C18 1.421(4) . ?
C18 C19 1.368(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.539(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 O2 93.59(10) . . ?
O1 Cu1 N1 169.70(11) . . ?
O2 Cu1 N1 92.12(11) . . ?
O1 Cu1 N2 90.44(11) . . ?
O2 Cu1 N2 168.58(10) . . ?
N1 Cu1 N2 82.40(12) . . ?
O1 Cu1 O3 93.52(10) . . ?
O2 Cu1 O3 104.97(9) . . ?
N1 Cu1 O3 93.27(11) . . ?
N2 Cu1 O3 85.41(10) . . ?
C13 S1 C16 92.09(17) . . ?
C17 O1 Cu1 126.0(2) . . ?
C19 O2 Cu1 121.3(2) . . ?
N3 O3 Cu1 124.75(18) . . ?
C5 N1 C1 118.5(3) . . ?
C5 N1 Cu1 128.8(2) . . ?
C1 N1 Cu1 112.5(2) . . ?
C10 N2 C6 118.7(3) . . ?
C10 N2 Cu1 129.5(2) . . ?
C6 N2 Cu1 111.6(2) . . ?
O4 N3 O5 121.7(3) . . ?
O4 N3 O3 118.7(2) . . ?
O5 N3 O3 119.6(3) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 C6 116.0(3) . . ?
C2 C1 C6 120.6(3) . . ?
C1 C2 C3 117.0(3) . . ?
C1 C2 C11 118.8(3) . . ?
C3 C2 C11 124.2(3) . . ?
C4 C3 C2 119.2(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 120.0(3) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 121.8(3) . . ?
N1 C5 H5 119.1 . . ?
C4 C5 H5 119.1 . . ?
N2 C6 C7 123.2(3) . . ?
N2 C6 C1 116.9(3) . . ?
C7 C6 C1 119.8(3) . . ?
C6 C7 C8 116.6(3) . . ?
C6 C7 C12 118.6(3) . . ?
C8 C7 C12 124.7(3) . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 119.2(3) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 122.1(3) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C12 C11 C2 120.6(3) . . ?
C12 C11 H11 119.7 . . ?
C2 C11 H11 119.7 . . ?
C11 C12 C7 121.5(3) . . ?
C11 C12 H12 119.3 . . ?
C7 C12 H12 119.3 . . ?
C14 C13 S1 112.0(3) . . ?
C14 C13 H13 124.0 . . ?
S1 C13 H13 124.0 . . ?
C13 C14 C15 112.4(3) . . ?
C13 C14 H14 123.8 . . ?
C15 C14 H14 123.8 . . ?
C16 C15 C14 112.8(3) . . ?
C16 C15 H15 123.6 . . ?
C14 C15 H15 123.6 . . ?
C15 C16 C17 130.6(3) . . ?
C15 C16 S1 110.7(3) . . ?
C17 C16 S1 118.7(2) . . ?
O1 C17 C18 124.1(3) . . ?
O1 C17 C16 116.4(3) . . ?
C18 C17 C16 119.5(3) . . ?
C19 C18 C17 122.4(3) . . ?
C19 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
O2 C19 C18 130.1(3) . . ?
O2 C19 C20 112.9(3) . . ?
C18 C19 C20 116.9(3) . . ?
F3 C20 F1 107.4(3) . . ?
F3 C20 F2 106.5(3) . . ?
F1 C20 F2 106.8(3) . . ?
F3 C20 C19 112.2(3) . . ?
F1 C20 C19 112.9(3) . . ?
F2 C20 C19 110.7(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O3 N3 O4 -171.1(2) . . . . ?
Cu1 O3 N3 O5 10.7(4) . . . . ?
C5 N1 C1 C2 0.6(5) . . . . ?
Cu1 N1 C1 C2 -176.4(2) . . . . ?
C5 N1 C1 C6 -178.0(3) . . . . ?
Cu1 N1 C1 C6 5.0(3) . . . . ?
N1 C1 C2 C3 -0.6(5) . . . . ?
C6 C1 C2 C3 178.0(3) . . . . ?
N1 C1 C2 C11 179.5(3) . . . . ?
C6 C1 C2 C11 -1.9(4) . . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C11 C2 C3 C4 179.7(3) . . . . ?
C2 C3 C4 C5 1.0(5) . . . . ?
C1 N1 C5 C4 0.2(5) . . . . ?
Cu1 N1 C5 C4 176.6(2) . . . . ?
C3 C4 C5 N1 -1.0(5) . . . . ?
C10 N2 C6 C7 0.2(5) . . . . ?
Cu1 N2 C6 C7 176.0(2) . . . . ?
C10 N2 C6 C1 179.2(3) . . . . ?
Cu1 N2 C6 C1 -5.1(3) . . . . ?
N1 C1 C6 N2 0.1(4) . . . . ?
C2 C1 C6 N2 -178.6(3) . . . . ?
N1 C1 C6 C7 179.1(3) . . . . ?
C2 C1 C6 C7 0.4(4) . . . . ?
N2 C6 C7 C8 1.4(5) . . . . ?
C1 C6 C7 C8 -177.6(3) . . . . ?
N2 C6 C7 C12 -179.9(3) . . . . ?
C1 C6 C7 C12 1.1(4) . . . . ?
C6 C7 C8 C9 -1.5(5) . . . . ?
C12 C7 C8 C9 179.8(3) . . . . ?
C7 C8 C9 C10 0.2(5) . . . . ?
C6 N2 C10 C9 -1.6(5) . . . . ?
Cu1 N2 C10 C9 -176.6(2) . . . . ?
C8 C9 C10 N2 1.4(5) . . . . ?
C1 C2 C11 C12 1.8(5) . . . . ?
C3 C2 C11 C12 -178.0(3) . . . . ?
C2 C11 C12 C7 -0.2(5) . . . . ?
C6 C7 C12 C11 -1.3(5) . . . . ?
C8 C7 C12 C11 177.3(3) . . . . ?
C16 S1 C13 C14 -0.2(3) . . . . ?
S1 C13 C14 C15 0.4(4) . . . . ?
C13 C14 C15 C16 -0.3(4) . . . . ?
C14 C15 C16 C17 179.5(3) . . . . ?
C14 C15 C16 S1 0.2(4) . . . . ?
C13 S1 C16 C15 0.0(3) . . . . ?
C13 S1 C16 C17 -179.4(3) . . . . ?
Cu1 O1 C17 C18 7.0(4) . . . . ?
Cu1 O1 C17 C16 -172.4(2) . . . . ?
C15 C16 C17 O1 -176.5(3) . . . . ?
S1 C16 C17 O1 2.8(4) . . . . ?
C15 C16 C17 C18 4.1(5) . . . . ?
S1 C16 C17 C18 -176.5(2) . . . . ?
O1 C17 C18 C19 3.3(5) . . . . ?
C16 C17 C18 C19 -177.3(3) . . . . ?
Cu1 O2 C19 C18 -12.9(5) . . . . ?
Cu1 O2 C19 C20 164.12(19) . . . . ?
C17 C18 C19 O2 0.3(5) . . . . ?
C17 C18 C19 C20 -176.7(3) . . . . ?
O2 C19 C20 F3 27.4(4) . . . . ?
C18 C19 C20 F3 -155.1(3) . . . . ?
O2 C19 C20 F1 148.9(3) . . . . ?
C18 C19 C20 F1 -33.6(4) . . . . ?
O2 C19 C20 F2 -91.4(3) . . . . ?
C18 C19 C20 F2 86.1(4) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
####################################################################### 
# 
# 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_cmpd5_CuTTAtmenCl
_database_code_depnum_ccdc_archive 'CCDC 2056495'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Cl Cu F3 N2 O2 S'
_chemical_formula_sum            'C14 H20 Cl Cu F3 N2 O2 S'
_chemical_formula_weight         436.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.1537(14)
_cell_length_b                   13.5200(19)
_cell_length_c                   13.2892(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.416(2)
_cell_angle_gamma                90
_cell_volume                     1794.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    9937
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      28.88

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.550
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    1.521
_shelx_estimated_absorpt_T_min   0.488
_shelx_estimated_absorpt_T_max   0.618
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_T_max  0.6945
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            28058
_diffrn_reflns_av_unetI/netI     0.0143
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.167
_diffrn_reflns_theta_max         28.917
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4718
_reflns_number_gt                4273
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+0.5359P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4718
_refine_ls_number_parameters     221
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0284
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0703
_refine_ls_wR_factor_gt          0.0689
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.76159(2) 0.52906(2) 0.75805(2) 0.02084(6) Uani 1 1 d . . . . .
Cl1 Cl 0.88926(4) 0.67430(3) 0.84267(3) 0.03131(9) Uani 1 1 d . . . . .
S1 S 0.31332(4) 0.63979(3) 0.75041(3) 0.02909(9) Uani 1 1 d . . . . .
F1 F 0.66333(11) 0.61328(10) 0.36843(7) 0.0502(3) Uani 1 1 d . . . . .
F2 F 0.82376(13) 0.69692(8) 0.45631(9) 0.0518(3) Uani 1 1 d . . . . .
F3 F 0.84391(12) 0.54149(8) 0.43676(8) 0.0465(3) Uani 1 1 d . . . . .
O1 O 0.57909(10) 0.58258(8) 0.72696(7) 0.0280(2) Uani 1 1 d . . . . .
O2 O 0.79157(10) 0.55959(9) 0.62143(8) 0.0321(2) Uani 1 1 d . . . . .
N1 N 0.90826(11) 0.42058(9) 0.77098(9) 0.0228(2) Uani 1 1 d . . . . .
N2 N 0.70998(12) 0.46807(9) 0.88567(9) 0.0235(2) Uani 1 1 d . . . . .
C1 C 0.51748(12) 0.61499(9) 0.64222(10) 0.0197(2) Uani 1 1 d . . . . .
C2 C 0.38083(13) 0.64996(10) 0.64068(10) 0.0208(2) Uani 1 1 d . . . . .
C3 C 0.29310(14) 0.69452(12) 0.56398(12) 0.0279(3) Uani 1 1 d . . . . .
H3 H 0.3121 0.7076 0.4994 0.034 Uiso 1 1 calc R U . . .
C4 C 0.16999(15) 0.71854(12) 0.59389(13) 0.0339(3) Uani 1 1 d . . . . .
H4 H 0.0987 0.7481 0.5506 0.041 Uiso 1 1 calc R U . . .
C5 C 0.16712(15) 0.69371(12) 0.69262(13) 0.0329(3) Uani 1 1 d . . . . .
H5 H 0.0943 0.7048 0.7248 0.039 Uiso 1 1 calc R U . . .
C6 C 0.57312(13) 0.62122(10) 0.55204(10) 0.0226(3) Uani 1 1 d . . . . .
H6 H 0.5201 0.6441 0.4921 0.027 Uiso 1 1 calc R U . . .
C7 C 0.70375(13) 0.59422(10) 0.55067(10) 0.0210(2) Uani 1 1 d . . . . .
C8 C 0.75827(15) 0.61126(11) 0.45180(10) 0.0268(3) Uani 1 1 d . . . . .
C9 C 0.89223(17) 0.35686(13) 0.67889(13) 0.0368(4) Uani 1 1 d . . . . .
H9A H 0.8994 0.3965 0.6202 0.055 Uiso 1 1 calc R U . . .
H9B H 0.8060 0.3256 0.6688 0.055 Uiso 1 1 calc R U . . .
H9C H 0.9610 0.3072 0.6880 0.055 Uiso 1 1 calc R U . . .
C10 C 1.04226(14) 0.46630(11) 0.78438(13) 0.0295(3) Uani 1 1 d . . . . .
H10A H 1.1092 0.4154 0.7908 0.044 Uiso 1 1 calc R U . . .
H10B H 1.0565 0.5064 0.8450 0.044 Uiso 1 1 calc R U . . .
H10C H 1.0482 0.5068 0.7261 0.044 Uiso 1 1 calc R U . . .
C11 C 0.89306(16) 0.35912(12) 0.86103(12) 0.0331(3) Uani 1 1 d . . . . .
H11A H 0.9797 0.3334 0.8930 0.040 Uiso 1 1 calc R U . . .
H11B H 0.8347 0.3035 0.8389 0.040 Uiso 1 1 calc R U . . .
C12 C 0.83513(15) 0.41969(12) 0.93707(11) 0.0306(3) Uani 1 1 d . . . . .
H12A H 0.8164 0.3774 0.9918 0.037 Uiso 1 1 calc R U . . .
H12B H 0.8992 0.4695 0.9668 0.037 Uiso 1 1 calc R U . . .
C13 C 0.59958(16) 0.39610(13) 0.85669(13) 0.0356(3) Uani 1 1 d . . . . .
H13A H 0.5204 0.4303 0.8242 0.053 Uiso 1 1 calc R U . . .
H13B H 0.5822 0.3631 0.9169 0.053 Uiso 1 1 calc R U . . .
H13C H 0.6247 0.3483 0.8102 0.053 Uiso 1 1 calc R U . . .
C14 C 0.66900(17) 0.54152(12) 0.95599(12) 0.0325(3) Uani 1 1 d . . . . .
H14A H 0.5899 0.5752 0.9224 0.049 Uiso 1 1 calc R U . . .
H14B H 0.7398 0.5886 0.9754 0.049 Uiso 1 1 calc R U . . .
H14C H 0.6506 0.5086 1.0159 0.049 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9389(10) . ?
Cu1 O1 1.9625(10) . ?
Cu1 N2 2.0376(12) . ?
Cu1 N1 2.0751(12) . ?
Cu1 Cl1 2.5048(5) . ?
S1 C5 1.7066(16) . ?
S1 C2 1.7253(13) . ?
F1 C8 1.3310(17) . ?
F2 C8 1.3314(18) . ?
F3 C8 1.3224(17) . ?
O1 C1 1.2637(16) . ?
O2 C7 1.2631(17) . ?
N1 C10 1.4757(18) . ?
N1 C9 1.4814(19) . ?
N1 C11 1.4875(18) . ?
N2 C14 1.4742(19) . ?
N2 C13 1.4818(19) . ?
N2 C12 1.4818(18) . ?
C1 C6 1.4168(17) . ?
C1 C2 1.4625(17) . ?
C2 C3 1.3664(19) . ?
C3 C4 1.416(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.3790(18) . ?
C6 H6 0.9300 . ?
C7 C8 1.5325(17) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.501(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
O2 Cu1 O1 91.52(4) . . ?
O2 Cu1 N2 166.67(5) . . ?
O1 Cu1 N2 87.09(4) . . ?
O2 Cu1 N1 89.78(5) . . ?
O1 Cu1 N1 156.10(5) . . ?
N2 Cu1 N1 86.20(5) . . ?
O2 Cu1 Cl1 95.59(4) . . ?
O1 Cu1 Cl1 101.41(4) . . ?
N2 Cu1 Cl1 97.68(4) . . ?
N1 Cu1 Cl1 102.21(4) . . ?
C5 S1 C2 91.82(7) . . ?
C1 O1 Cu1 127.72(9) . . ?
C7 O2 Cu1 124.53(9) . . ?
C10 N1 C9 107.72(11) . . ?
C10 N1 C11 111.37(12) . . ?
C9 N1 C11 109.14(13) . . ?
C10 N1 Cu1 110.25(9) . . ?
C9 N1 Cu1 111.88(10) . . ?
C11 N1 Cu1 106.51(8) . . ?
C14 N2 C13 108.67(12) . . ?
C14 N2 C12 108.78(12) . . ?
C13 N2 C12 112.04(12) . . ?
C14 N2 Cu1 113.55(9) . . ?
C13 N2 Cu1 110.23(9) . . ?
C12 N2 Cu1 103.54(8) . . ?
O1 C1 C6 124.45(12) . . ?
O1 C1 C2 116.11(11) . . ?
C6 C1 C2 119.43(12) . . ?
C3 C2 C1 129.93(12) . . ?
C3 C2 S1 111.13(10) . . ?
C1 C2 S1 118.90(10) . . ?
C2 C3 C4 112.41(13) . . ?
C2 C3 H3 123.8 . . ?
C4 C3 H3 123.8 . . ?
C5 C4 C3 112.84(14) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
C4 C5 S1 111.78(11) . . ?
C4 C5 H5 124.1 . . ?
S1 C5 H5 124.1 . . ?
C7 C6 C1 121.80(12) . . ?
C7 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O2 C7 C6 129.76(12) . . ?
O2 C7 C8 112.22(11) . . ?
C6 C7 C8 117.96(12) . . ?
F3 C8 F1 106.61(12) . . ?
F3 C8 F2 106.89(13) . . ?
F1 C8 F2 107.48(13) . . ?
F3 C8 C7 111.82(12) . . ?
F1 C8 C7 113.41(12) . . ?
F2 C8 C7 110.31(12) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 110.31(12) . . ?
N1 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N1 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
N2 C12 C11 109.77(12) . . ?
N2 C12 H12A 109.7 . . ?
C11 C12 H12A 109.7 . . ?
N2 C12 H12B 109.7 . . ?
C11 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

_refine_diff_density_max         0.545
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
####################################################################### 
# 
# 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_cmpd2_CuTTAbipyNO3
_database_code_depnum_ccdc_archive 'CCDC 2056493'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT094_cmpd2_CuTTAbipyNO3  
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       4.65 Report
RESPONSE: There is a relatively strong ghost peak close to the Cu atom (ca.
1 Angstrom away) directly on the Cu-N bond. This is due to series 
termination effects.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cu F3 N3 O5 S, H2 o'
_chemical_formula_sum            'C18 H14 Cu F3 N3 O6 S'
_chemical_formula_weight         520.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   27.42(7)
_cell_length_b                   27.513(18)
_cell_length_c                   10.435(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7873(23)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5205
_cell_measurement_theta_min      2.22
_cell_measurement_theta_max      25.25

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_F_000             4208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.288
_shelx_estimated_absorpt_T_min   0.739
_shelx_estimated_absorpt_T_max   0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6678
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            18494
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0446
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.215
_diffrn_reflns_theta_max         26.773
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4201
_reflns_number_gt                3747
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.999

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0457P)²+12.8439P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.026(17)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         4201
_refine_ls_number_parameters     296
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0855
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31846(2) 0.23789(2) 0.50194(7) 0.01685(15) Uani 1 1 d . . . . .
C1 C 0.30518(19) 0.22633(18) 0.7846(5) 0.0207(10) Uani 1 1 d . . . . .
H1 H 0.311987 0.260101 0.790961 0.025 Uiso 1 1 calc R U . . .
F1 F 0.35280(12) 0.29351(12) 0.1048(3) 0.0301(7) Uani 1 1 d . . . . .
O1 O 0.31469(14) 0.26643(13) 0.3346(3) 0.0236(8) Uani 1 1 d . . . . .
N1 N 0.30458(15) 0.20556(15) 0.6669(4) 0.0180(9) Uani 1 1 d . . . . .
S1 S 0.34249(5) 0.37288(5) 0.77789(12) 0.0238(3) Uani 1 1 d . . . . .
C2 C 0.29633(19) 0.2006(2) 0.8954(5) 0.0232(12) Uani 1 1 d . . . . .
H2 H 0.296784 0.216415 0.976239 0.028 Uiso 1 1 calc R U . . .
F2 F 0.27716(12) 0.31110(13) 0.1195(3) 0.0331(8) Uani 1 1 d . . . . .
O2 O 0.32303(14) 0.30053(13) 0.5834(3) 0.0233(8) Uani 1 1 d . . . . .
N2 N 0.30484(15) 0.17192(15) 0.4357(4) 0.0176(9) Uani 1 1 d . . . . .
O3 O 0.39931(14) 0.22510(15) 0.5401(4) 0.0297(9) Uani 1 1 d . . . . .
C3 C 0.28691(19) 0.15191(19) 0.8873(5) 0.0209(11) Uani 1 1 d . . . . .
H3 H 0.280740 0.133479 0.962509 0.025 Uiso 1 1 calc R U . . .
F3 F 0.33118(15) 0.36731(11) 0.1376(3) 0.0366(9) Uani 1 1 d . . . . .
N3 N 0.42993(18) 0.23727(15) 0.4573(4) 0.0231(10) Uani 1 1 d . . . . .
O4 O 0.42234(19) 0.23062(16) 0.3424(4) 0.0446(12) Uani 1 1 d . . . . .
C4 C 0.28643(17) 0.12935(18) 0.7659(5) 0.0202(10) Uani 1 1 d . . . . .
H4 H 0.280105 0.095534 0.758018 0.024 Uiso 1 1 calc R U . . .
O5 O 0.46881(13) 0.25715(15) 0.4919(5) 0.0339(9) Uani 1 1 d D . . . .
C5 C 0.29535(18) 0.15739(19) 0.6591(5) 0.0175(11) Uani 1 1 d . . . . .
C9 C 0.29767(18) 0.11143(17) 0.2753(5) 0.0209(11) Uani 1 1 d . . . . .
H9 H 0.298321 0.102859 0.187079 0.025 Uiso 1 1 calc R U . . .
C8 C 0.28831(19) 0.07704(18) 0.3670(5) 0.0221(11) Uani 1 1 d . . . . .
H8 H 0.282578 0.044232 0.342964 0.027 Uiso 1 1 calc R U . . .
C7 C 0.28722(17) 0.09032(17) 0.4952(5) 0.0194(10) Uani 1 1 d . . . . .
H7 H 0.280831 0.066926 0.560054 0.023 Uiso 1 1 calc R U . . .
O6 O 0.47036(16) 0.29340(15) 0.7617(4) 0.0410(10) Uani 1 1 d D . . . .
H6A H 0.5012(9) 0.2780(17) 0.776(4) 0.061 Uiso 1 1 d D U . . .
H6B H 0.4701(16) 0.3002(8) 0.6716(5) 0.061 Uiso 1 1 d D U . . .
C6 C 0.29565(16) 0.13826(17) 0.5262(4) 0.0165(10) Uani 1 1 d . . . . .
C10 C 0.30609(19) 0.15845(18) 0.3130(5) 0.0194(11) Uani 1 1 d . . . . .
H10 H 0.313053 0.182221 0.249589 0.023 Uiso 1 1 calc R U . . .
C11 C 0.32232(18) 0.31105(18) 0.3120(4) 0.0156(10) Uani 1 1 d . . . . .
C12 C 0.32074(19) 0.32103(19) 0.1673(5) 0.0202(11) Uani 1 1 d . . . . .
C13 C 0.33050(18) 0.34861(18) 0.3961(5) 0.0173(10) Uani 1 1 d . . . . .
H13 H 0.337067 0.380212 0.363806 0.021 Uiso 1 1 calc R U . . .
C14 C 0.32929(16) 0.34089(17) 0.5308(5) 0.0154(10) Uani 1 1 d . . . . .
C15 C 0.33446(18) 0.38298(19) 0.6154(5) 0.0190(11) Uani 1 1 d . . . . .
C16 C 0.33149(19) 0.43178(19) 0.5894(5) 0.0206(11) Uani 1 1 d . . . . .
H16 H 0.327331 0.444731 0.505740 0.025 Uiso 1 1 calc R U . . .
C17 C 0.3353(2) 0.4604(2) 0.7000(5) 0.0246(12) Uani 1 1 d . . . . .
H17 H 0.333553 0.494858 0.699186 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3416(2) 0.4338(2) 0.8089(5) 0.0274(12) Uani 1 1 d . . . . .
H18 H 0.345151 0.447511 0.891968 0.033 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.918(4) . ?
Cu1 O2 1.926(4) . ?
Cu1 N1 1.975(4) . ?
Cu1 N2 1.978(4) . ?
Cu1 O3 2.280(7) . ?
C1 N1 1.355(7) . ?
C1 C2 1.378(7) . ?
C1 H1 0.9500 . ?
F1 C12 1.331(6) . ?
O1 C11 1.267(6) . ?
N1 C5 1.352(7) . ?
S1 C18 1.708(6) . ?
S1 C15 1.732(5) . ?
C2 C3 1.366(8) . ?
C2 H2 0.9500 . ?
F2 C12 1.323(7) . ?
O2 C14 1.251(6) . ?
N2 C10 1.334(6) . ?
N2 C6 1.346(6) . ?
O3 N3 1.251(6) . ?
C3 C4 1.410(7) . ?
C3 H3 0.9500 . ?
F3 C12 1.342(6) . ?
N3 O4 1.231(6) . ?
N3 O5 1.251(6) . ?
C4 C5 1.377(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.483(7) . ?
C9 C8 1.371(7) . ?
C9 C10 1.372(7) . ?
C9 H9 0.9500 . ?
C8 C7 1.387(8) . ?
C8 H8 0.9500 . ?
C7 C6 1.378(7) . ?
C7 H7 0.9500 . ?
O6 H6A 0.958(3) . ?
O6 H6B 0.9584(16) . ?
C10 H10 0.9500 . ?
C11 C13 1.374(7) . ?
C11 C12 1.536(7) . ?
C13 C14 1.421(7) . ?
C13 H13 0.9500 . ?
C14 C15 1.463(7) . ?
C15 C16 1.372(7) . ?
C16 C17 1.401(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.362(8) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

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 92.23(15) . . ?
O1 Cu1 N1 165.46(17) . . ?
O2 Cu1 N1 91.78(17) . . ?
O1 Cu1 N2 92.72(16) . . ?
O2 Cu1 N2 171.06(17) . . ?
N1 Cu1 N2 81.65(18) . . ?
O1 Cu1 O3 105.95(15) . . ?
O2 Cu1 O3 89.87(16) . . ?
N1 Cu1 O3 88.03(17) . . ?
N2 Cu1 O3 95.92(17) . . ?
N1 C1 C2 122.8(5) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C11 O1 Cu1 123.8(3) . . ?
C5 N1 C1 118.1(4) . . ?
C5 N1 Cu1 115.2(3) . . ?
C1 N1 Cu1 126.7(3) . . ?
C18 S1 C15 91.5(3) . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C14 O2 Cu1 127.6(3) . . ?
C10 N2 C6 119.1(4) . . ?
C10 N2 Cu1 125.9(3) . . ?
C6 N2 Cu1 114.9(3) . . ?
N3 O3 Cu1 119.4(3) . . ?
C2 C3 C4 119.3(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
O4 N3 O3 121.3(5) . . ?
O4 N3 O5 119.3(5) . . ?
O3 N3 O5 119.3(5) . . ?
C5 C4 C3 118.6(5) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.3(5) . . ?
N1 C5 C6 113.8(4) . . ?
C4 C5 C6 124.0(5) . . ?
C8 C9 C10 118.8(5) . . ?
C8 C9 H9 120.6 . . ?
C10 C9 H9 120.6 . . ?
C9 C8 C7 119.7(5) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C6 C7 C8 118.4(5) . . ?
C6 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
H6A O6 H6B 104.4(2) . . ?
N2 C6 C7 121.7(4) . . ?
N2 C6 C5 114.4(4) . . ?
C7 C6 C5 123.9(4) . . ?
N2 C10 C9 122.3(5) . . ?
N2 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
O1 C11 C13 129.6(5) . . ?
O1 C11 C12 110.5(4) . . ?
C13 C11 C12 119.9(5) . . ?
F2 C12 F1 107.1(4) . . ?
F2 C12 F3 107.5(4) . . ?
F1 C12 F3 106.6(4) . . ?
F2 C12 C11 111.1(4) . . ?
F1 C12 C11 111.2(4) . . ?
F3 C12 C11 113.0(4) . . ?
C11 C13 C14 121.0(4) . . ?
C11 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
O2 C14 C13 124.7(4) . . ?
O2 C14 C15 116.8(4) . . ?
C13 C14 C15 118.4(4) . . ?
C16 C15 C14 130.5(5) . . ?
C16 C15 S1 111.0(4) . . ?
C14 C15 S1 118.4(4) . . ?
C15 C16 C17 112.5(5) . . ?
C15 C16 H16 123.8 . . ?
C17 C16 H16 123.8 . . ?
C18 C17 C16 113.3(5) . . ?
C18 C17 H17 123.3 . . ?
C16 C17 H17 123.3 . . ?
C17 C18 S1 111.7(4) . . ?
C17 C18 H18 124.1 . . ?
S1 C18 H18 124.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C1 N1 C5 -0.7(7) . . . . ?
C2 C1 N1 Cu1 -178.1(4) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 0.0(8) . . . . ?
Cu1 O3 N3 O4 -40.4(6) . . . . ?
Cu1 O3 N3 O5 138.7(4) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C1 N1 C5 C4 0.3(7) . . . . ?
Cu1 N1 C5 C4 178.0(4) . . . . ?
C1 N1 C5 C6 -179.9(4) . . . . ?
Cu1 N1 C5 C6 -2.1(5) . . . . ?
C3 C4 C5 N1 0.1(7) . . . . ?
C3 C4 C5 C6 -179.7(5) . . . . ?
C10 C9 C8 C7 0.4(7) . . . . ?
C9 C8 C7 C6 0.1(7) . . . . ?
C10 N2 C6 C7 -0.4(7) . . . . ?
Cu1 N2 C6 C7 -177.7(3) . . . . ?
C10 N2 C6 C5 179.8(4) . . . . ?
Cu1 N2 C6 C5 2.5(5) . . . . ?
C8 C7 C6 N2 -0.1(7) . . . . ?
C8 C7 C6 C5 179.7(4) . . . . ?
N1 C5 C6 N2 -0.2(6) . . . . ?
C4 C5 C6 N2 179.6(4) . . . . ?
N1 C5 C6 C7 179.9(4) . . . . ?
C4 C5 C6 C7 -0.2(7) . . . . ?
C6 N2 C10 C9 0.9(7) . . . . ?
Cu1 N2 C10 C9 177.9(4) . . . . ?
C8 C9 C10 N2 -0.9(8) . . . . ?
Cu1 O1 C11 C13 -5.9(8) . . . . ?
Cu1 O1 C11 C12 175.1(3) . . . . ?
O1 C11 C12 F2 62.4(6) . . . . ?
C13 C11 C12 F2 -116.8(5) . . . . ?
O1 C11 C12 F1 -56.8(6) . . . . ?
C13 C11 C12 F1 124.1(5) . . . . ?
O1 C11 C12 F3 -176.7(4) . . . . ?
C13 C11 C12 F3 4.2(7) . . . . ?
O1 C11 C13 C14 -2.7(8) . . . . ?
C12 C11 C13 C14 176.3(5) . . . . ?
Cu1 O2 C14 C13 5.2(7) . . . . ?
Cu1 O2 C14 C15 -176.4(3) . . . . ?
C11 C13 C14 O2 3.1(8) . . . . ?
C11 C13 C14 C15 -175.2(5) . . . . ?
O2 C14 C15 C16 -164.6(5) . . . . ?
C13 C14 C15 C16 13.9(8) . . . . ?
O2 C14 C15 S1 11.4(6) . . . . ?
C13 C14 C15 S1 -170.1(4) . . . . ?
C18 S1 C15 C16 0.1(4) . . . . ?
C18 S1 C15 C14 -176.6(4) . . . . ?
C14 C15 C16 C17 175.7(5) . . . . ?
S1 C15 C16 C17 -0.5(6) . . . . ?
C15 C16 C17 C18 0.7(7) . . . . ?
C16 C17 C18 S1 -0.6(6) . . . . ?
C15 S1 C18 C17 0.3(4) . . . . ?

_refine_diff_density_max         1.303
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.076


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
####################################################################### 
# 
# 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_cmpd7_CuTTA2tmen
_database_code_depnum_ccdc_archive 'CCDC 2056497'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H24 Cu F6 N2 O4 S2'
_chemical_formula_sum            'C22 H24 Cu F6 N2 O4 S2'
_chemical_formula_weight         622.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.633(3)
_cell_length_b                   9.9312(18)
_cell_length_c                   16.773(3)
_cell_angle_alpha                90
_cell_angle_beta                 108.801(2)
_cell_angle_gamma                90
_cell_volume                     2622.9(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    9914
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.92

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             1268
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.066
_shelx_estimated_absorpt_T_min   0.567
_shelx_estimated_absorpt_T_max   0.675
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6239
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            43348
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5145
_reflns_number_gt                4623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 The displacement parameters of the fluorine atoms of each CF3 group 
 were restrained with DELU keyword in ShelXL  input, respectively ('rigid 
 bond' restraint for all bonds in the connectivity list. 
 Standard values of 0.01 for both parameters s1 and s2 were used).
 The displacement parameters of the fluorine atoms of each CF3 group were
 were restrained to the same values with similarity restraint SIMU. 
 The displacement parameters of atoms C7 and C8 of a thienyl group were
 were restrained to the same values with similarity restraint SIMU. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.5936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5145
_refine_ls_number_parameters     403
_refine_ls_number_restraints     43
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0934
_refine_ls_wR_factor_gt          0.0908
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.149
_refine_ls_shift/su_max          0.019
_refine_ls_shift/su_mean         0.001

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 0.82972(2) 0.51329(2) 0.79257(2) 0.02930(9) Uani 1 1 d . . . . .
S1A S 0.68089(18) 0.2117(2) 0.54847(13) 0.0443(4) Uani 0.652(4) 1 d . . P A 1
C6A C 0.5846(11) 0.4091(18) 0.4798(7) 0.072(4) Uani 0.652(4) 1 d . . P A 1
H6A H 0.5587 0.4955 0.4704 0.086 Uiso 0.652(4) 1 calc R U P A 1
S1B S 0.5820(5) 0.4269(9) 0.4563(4) 0.0657(13) Uani 0.348(4) 1 d . . P A 2
C6B C 0.6618(12) 0.233(2) 0.5368(12) 0.081(10) Uani 0.348(4) 1 d . . P A 2
H6B H 0.7028 0.1794 0.5770 0.097 Uiso 0.348(4) 1 calc R U P A 2
S2A S 0.54095(11) 0.4871(2) 0.75133(13) 0.0503(5) Uani 0.647(4) 1 d . . P B 3
C14A C 0.5363(8) 0.6821(13) 0.8467(6) 0.059(3) Uani 0.647(4) 1 d . . P B 3
H14A H 0.5518 0.7588 0.8822 0.070 Uiso 0.647(4) 1 calc R U P B 3
S2B S 0.5366(4) 0.6998(6) 0.8709(3) 0.0509(9) Uani 0.353(4) 1 d . . P B 4
C14B C 0.5355(11) 0.5238(15) 0.7680(10) 0.064(5) Uani 0.353(4) 1 d . . P B 4
H14B H 0.5535 0.4598 0.7351 0.076 Uiso 0.353(4) 1 calc R U P B 4
F1A F 0.6730(9) 0.8698(16) 0.5654(7) 0.064(2) Uani 0.5 1 d . U P C 5
F2A F 0.8057(7) 0.9049(12) 0.6251(5) 0.0668(19) Uani 0.5 1 d . U P C 5
F3A F 0.7238(4) 0.9132(12) 0.6972(6) 0.0647(16) Uani 0.5 1 d . U P C 5
F1B F 0.7934(7) 0.8942(13) 0.5977(4) 0.0606(16) Uani 0.5 1 d . U P C 6
F2B F 0.7530(5) 0.9214(12) 0.7048(7) 0.075(2) Uani 0.5 1 d . U P C 6
F3B F 0.6630(9) 0.8790(16) 0.5838(8) 0.064(2) Uani 0.5 1 d . U P C 6
F4 F 0.90028(12) 0.84486(15) 1.03555(9) 0.0831(6) Uani 1 1 d . . . . .
F5 F 0.90700(13) 0.92696(18) 0.92051(14) 0.0944(6) Uani 1 1 d . . . . .
F6 F 0.80125(9) 0.96613(13) 0.96046(9) 0.0586(4) Uani 1 1 d . . . . .
O1 O 0.81773(8) 0.67711(13) 0.72131(8) 0.0371(3) Uani 1 1 d . . . . .
O2 O 0.77044(9) 0.40848(13) 0.66614(8) 0.0390(3) Uani 1 1 d . . . . .
O3 O 0.86957(8) 0.65732(14) 0.90527(9) 0.0412(3) Uani 1 1 d . . . . .
O4 O 0.71546(8) 0.53304(14) 0.80085(9) 0.0396(3) Uani 1 1 d . . . . .
N1 N 0.95277(10) 0.48348(15) 0.79496(10) 0.0330(3) Uani 1 1 d . . . . .
N2 N 0.84080(10) 0.33233(16) 0.85537(10) 0.0358(3) Uani 1 1 d . . . . .
C1 C 0.75369(11) 0.69691(18) 0.65568(11) 0.0330(4) Uani 1 1 d . . . . .
C2 C 0.73860(12) 0.84724(19) 0.63578(13) 0.0404(4) Uani 1 1 d . . . . .
C3 C 0.70094(12) 0.60692(19) 0.60198(12) 0.0363(4) Uani 1 1 d . . . . .
H3 H 0.6535 0.6408 0.5581 0.044 Uiso 1 1 calc R U . . .
C4 C 0.71363(12) 0.46464(19) 0.60858(11) 0.0340(4) Uani 1 1 d . . . . .
C5 C 0.65786(13) 0.3770(2) 0.54265(12) 0.0374(4) Uani 1 1 d . . . . .
C7 C 0.5511(2) 0.2821(3) 0.42703(19) 0.0808(9) Uani 1 1 d . U . . .
H7 H 0.5047 0.2790 0.3760 0.097 Uiso 1 1 calc R U . A 1
C8 C 0.59826(19) 0.1767(3) 0.46508(15) 0.0634(6) Uani 1 1 d . U . . .
H8 H 0.5850 0.0871 0.4453 0.076 Uiso 1 1 calc R U . A 1
C9 C 0.81612(12) 0.74219(19) 0.90972(11) 0.0338(4) Uani 1 1 d . . . . .
C10 C 0.85610(13) 0.8706(2) 0.95639(13) 0.0412(4) Uani 1 1 d . . . . .
C11 C 0.72806(12) 0.73482(19) 0.88009(11) 0.0360(4) Uani 1 1 d . . . . .
H11 H 0.6964 0.8068 0.8926 0.043 Uiso 1 1 calc R U . . .
C12 C 0.68357(11) 0.62612(19) 0.83249(11) 0.0347(4) Uani 1 1 d . . . . .
C13 C 0.59166(12) 0.6132(2) 0.81639(12) 0.0384(4) Uani 1 1 d . . . . .
C15 C 0.45085(16) 0.6249(4) 0.81872(19) 0.0723(8) Uani 1 1 d . U . . .
H15 H 0.4043 0.6541 0.8354 0.087 Uiso 1 1 calc R U . B 3
C16 C 0.44968(17) 0.5259(3) 0.76627(19) 0.0684(7) Uani 1 1 d . U . . .
H16 H 0.3988 0.4785 0.7381 0.082 Uiso 1 1 calc R U . B 3
C17 C 0.98471(12) 0.3658(2) 0.85051(14) 0.0437(5) Uani 1 1 d . . . . .
H17A H 1.0066 0.3958 0.9099 0.052 Uiso 1 1 calc R U . . .
H17B H 1.0320 0.3231 0.8361 0.052 Uiso 1 1 calc R U . . .
C18 C 0.91482(12) 0.2660(2) 0.84017(14) 0.0434(5) Uani 1 1 d . . . . .
H18A H 0.8974 0.2282 0.7825 0.052 Uiso 1 1 calc R U . . .
H18B H 0.9353 0.1910 0.8805 0.052 Uiso 1 1 calc R U . . .
C19 C 1.00612(13) 0.6030(2) 0.82884(15) 0.0451(5) Uani 1 1 d . . . . .
H19A H 1.0645 0.5855 0.8300 0.068 Uiso 1 1 calc R U . . .
H19B H 1.0057 0.6215 0.8861 0.068 Uiso 1 1 calc R U . . .
H19C H 0.9835 0.6810 0.7928 0.068 Uiso 1 1 calc R U . . .
C20 C 0.95671(14) 0.4571(2) 0.70973(13) 0.0465(5) Uani 1 1 d . . . . .
H20A H 0.9227 0.3773 0.6862 0.070 Uiso 1 1 calc R U . . .
H20B H 1.0158 0.4415 0.7129 0.070 Uiso 1 1 calc R U . . .
H20C H 0.9343 0.5350 0.6735 0.070 Uiso 1 1 calc R U . . .
C21 C 0.85485(18) 0.3527(3) 0.94528(14) 0.0593(6) Uani 1 1 d . . . . .
H21A H 0.8056 0.3985 0.9527 0.089 Uiso 1 1 calc R U . . .
H21B H 0.9057 0.4080 0.9694 0.089 Uiso 1 1 calc R U . . .
H21C H 0.8627 0.2653 0.9739 0.089 Uiso 1 1 calc R U . . .
C22 C 0.76559(13) 0.2440(2) 0.82059(14) 0.0481(5) Uani 1 1 d . . . . .
H22A H 0.7555 0.2296 0.7604 0.072 Uiso 1 1 calc R U . . .
H22B H 0.7157 0.2869 0.8285 0.072 Uiso 1 1 calc R U . . .
H22C H 0.7759 0.1572 0.8499 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.9596(14) . ?
Cu1 O1 1.9904(13) . ?
Cu1 N1 2.0556(16) . ?
Cu1 N2 2.0610(16) . ?
Cu1 O2 2.2814(13) . ?
Cu1 O3 2.2916(14) . ?
S1A C8 1.651(4) . ?
S1A C5 1.681(3) . ?
C6A C5 1.367(14) . ?
C6A C7 1.539(18) . ?
C6A H6A 0.9500 . ?
S1B C7 1.553(10) . ?
S1B C5 1.661(7) . ?
C6B C8 1.433(19) . ?
C6B C5 1.439(19) . ?
C6B H6B 0.9500 . ?
S2A C16 1.662(3) . ?
S2A C13 1.696(3) . ?
C14A C13 1.370(10) . ?
C14A C15 1.460(13) . ?
C14A H14A 0.9500 . ?
S2B C15 1.596(7) . ?
S2B C13 1.719(5) . ?
C14B C13 1.354(16) . ?
C14B C16 1.418(16) . ?
C14B H14B 0.9500 . ?
F1A C2 1.343(13) . ?
F2A C2 1.316(12) . ?
F3A C2 1.310(10) . ?
F1B C2 1.354(12) . ?
F2B C2 1.327(11) . ?
F3B C2 1.316(13) . ?
F4 C10 1.319(2) . ?
F5 C10 1.312(3) . ?
F6 C10 1.333(2) . ?
O1 C1 1.276(2) . ?
O2 C4 1.244(2) . ?
O3 C9 1.245(2) . ?
O4 C12 1.265(2) . ?
N1 C20 1.475(3) . ?
N1 C17 1.482(2) . ?
N1 C19 1.481(3) . ?
N2 C21 1.464(3) . ?
N2 C22 1.485(2) . ?
N2 C18 1.489(3) . ?
C1 C3 1.368(3) . ?
C1 C2 1.533(3) . ?
C3 C4 1.428(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.476(3) . ?
C7 C8 1.341(4) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C11 1.389(3) . ?
C9 C10 1.532(3) . ?
C11 C12 1.403(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.470(3) . ?
C15 C16 1.316(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.495(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 Cu1 O1 92.81(6) . . ?
O4 Cu1 N1 174.49(6) . . ?
O1 Cu1 N1 92.05(6) . . ?
O4 Cu1 N2 88.86(6) . . ?
O1 Cu1 N2 174.13(6) . . ?
N1 Cu1 N2 86.56(6) . . ?
O4 Cu1 O2 88.46(5) . . ?
O1 Cu1 O2 83.40(5) . . ?
N1 Cu1 O2 94.69(6) . . ?
N2 Cu1 O2 91.03(6) . . ?
O4 Cu1 O3 84.74(5) . . ?
O1 Cu1 O3 86.07(5) . . ?
N1 Cu1 O3 93.00(6) . . ?
N2 Cu1 O3 99.69(6) . . ?
O2 Cu1 O3 167.17(5) . . ?
C8 S1A C5 92.58(19) . . ?
C5 C6A C7 108.7(12) . . ?
C5 C6A H6A 125.7 . . ?
C7 C6A H6A 125.7 . . ?
C7 S1B C5 94.6(4) . . ?
C8 C6B C5 114.0(12) . . ?
C8 C6B H6B 123.0 . . ?
C5 C6B H6B 123.0 . . ?
C16 S2A C13 91.20(16) . . ?
C13 C14A C15 112.8(7) . . ?
C13 C14A H14A 123.6 . . ?
C15 C14A H14A 123.6 . . ?
C15 S2B C13 90.6(3) . . ?
C13 C14B C16 119.9(8) . . ?
C13 C14B H14B 120.1 . . ?
C16 C14B H14B 120.1 . . ?
C1 O1 Cu1 122.55(12) . . ?
C4 O2 Cu1 120.62(12) . . ?
C9 O3 Cu1 116.73(12) . . ?
C12 O4 Cu1 130.58(13) . . ?
C20 N1 C17 110.49(16) . . ?
C20 N1 C19 107.81(16) . . ?
C17 N1 C19 109.96(16) . . ?
C20 N1 Cu1 111.20(13) . . ?
C17 N1 Cu1 106.19(12) . . ?
C19 N1 Cu1 111.21(12) . . ?
C21 N2 C22 108.73(17) . . ?
C21 N2 C18 111.80(17) . . ?
C22 N2 C18 108.04(16) . . ?
C21 N2 Cu1 111.35(14) . . ?
C22 N2 Cu1 112.90(12) . . ?
C18 N2 Cu1 103.96(11) . . ?
O1 C1 C3 130.33(17) . . ?
O1 C1 C2 111.74(16) . . ?
C3 C1 C2 117.89(16) . . ?
F3A C2 F2A 105.8(6) . . ?
F3B C2 F2B 108.0(7) . . ?
F3A C2 F1A 107.7(6) . . ?
F2A C2 F1A 107.0(8) . . ?
F3B C2 F1B 104.4(7) . . ?
F2B C2 F1B 105.1(6) . . ?
F3A C2 C1 112.0(5) . . ?
F3B C2 C1 115.6(8) . . ?
F2A C2 C1 111.5(5) . . ?
F2B C2 C1 112.3(5) . . ?
F1A C2 C1 112.5(7) . . ?
F1B C2 C1 110.5(6) . . ?
C1 C3 C4 123.25(17) . . ?
C1 C3 H3 118.4 . . ?
C4 C3 H3 118.4 . . ?
O2 C4 C3 124.06(18) . . ?
O2 C4 C5 116.98(17) . . ?
C3 C4 C5 118.94(16) . . ?
C6A C5 C4 128.9(8) . . ?
C6B C5 C4 127.3(7) . . ?
C6B C5 S1B 106.1(8) . . ?
C4 C5 S1B 126.5(3) . . ?
C6A C5 S1A 113.7(8) . . ?
C4 C5 S1A 117.11(16) . . ?
C8 C7 C6A 108.6(6) . . ?
C8 C7 S1B 119.3(3) . . ?
C8 C7 H7 125.7 . . ?
C6A C7 H7 125.7 . . ?
C7 C8 C6B 104.9(8) . . ?
C7 C8 S1A 116.0(2) . . ?
C7 C8 H8 122.0 . . ?
S1A C8 H8 122.0 . . ?
O3 C9 C11 129.36(18) . . ?
O3 C9 C10 113.19(16) . . ?
C11 C9 C10 117.44(16) . . ?
F5 C10 F4 108.2(2) . . ?
F5 C10 F6 105.89(18) . . ?
F4 C10 F6 104.77(17) . . ?
F5 C10 C9 111.02(17) . . ?
F4 C10 C9 111.23(16) . . ?
F6 C10 C9 115.28(17) . . ?
C9 C11 C12 123.10(17) . . ?
C9 C11 H11 118.4 . . ?
C12 C11 H11 118.4 . . ?
O4 C12 C11 125.84(17) . . ?
O4 C12 C13 114.27(18) . . ?
C11 C12 C13 119.89(17) . . ?
C14B C13 C12 130.1(6) . . ?
C14A C13 C12 132.2(6) . . ?
C14A C13 S2A 110.7(6) . . ?
C12 C13 S2A 117.06(16) . . ?
C14B C13 S2B 105.3(6) . . ?
C12 C13 S2B 124.0(2) . . ?
C16 C15 C14A 108.0(4) . . ?
C16 C15 S2B 122.2(3) . . ?
C16 C15 H15 126.0 . . ?
C14A C15 H15 126.0 . . ?
C15 C16 C14B 101.5(6) . . ?
C15 C16 S2A 117.2(2) . . ?
C15 C16 H16 121.4 . . ?
S2A C16 H16 121.4 . . ?
N1 C17 C18 110.01(16) . . ?
N1 C17 H17A 109.7 . . ?
C18 C17 H17A 109.7 . . ?
N1 C17 H17B 109.7 . . ?
C18 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
N2 C18 C17 109.96(17) . . ?
N2 C18 H18A 109.7 . . ?
C17 C18 H18A 109.7 . . ?
N2 C18 H18B 109.7 . . ?
C17 C18 H18B 109.7 . . ?
H18A C18 H18B 108.2 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 H20A 109.5 . . ?
N1 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N1 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N2 C22 H22A 109.5 . . ?
N2 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
N2 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_refine_diff_density_max         0.445
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.058


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
####################################################################### 
# 
# 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_cmpd6_CuTTAtmenNO3
_database_code_depnum_ccdc_archive 'CCDC 2056496'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H20 Cu F3 N3 O5 S'
_chemical_formula_sum            'C14 H20 Cu F3 N3 O5 S'
_chemical_formula_weight         462.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.4518(14)
_cell_length_b                   13.4241(18)
_cell_length_c                   13.3035(18)
_cell_angle_alpha                90
_cell_angle_beta                 96.356(2)
_cell_angle_gamma                90
_cell_volume                     1855.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    168(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.16
_cell_measurement_theta_max      28.72

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_F_000             948
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_absorpt_coefficient_mu    1.350
_shelx_estimated_absorpt_T_min   0.552
_shelx_estimated_absorpt_T_max   0.552
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4192
_exptl_absorpt_correction_T_max  0.4923
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      168(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker SMART-APEX'
_diffrn_detector                 'CCD area detector (Apex1)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            27678
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4054
_reflns_number_gt                3736
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Smart NT ver. 5.63 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+1.2966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0918
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.23587(2) 1.01827(2) 0.24488(2) 0.02419(9) Uani 1 1 d . . . . .
S1 S -0.17512(5) 0.87511(4) 0.26607(4) 0.03289(14) Uani 1 1 d . . . . .
F1 F 0.3293(2) 0.81665(13) -0.02584(14) 0.0744(6) Uani 1 1 d . . . . .
F2 F 0.18190(17) 0.88799(15) -0.12530(11) 0.0599(5) Uani 1 1 d . . . . .
F3 F 0.34765(16) 0.96792(11) -0.06880(12) 0.0484(4) Uani 1 1 d . . . . .
O1 O 0.06816(13) 0.95671(11) 0.22555(10) 0.0257(3) Uani 1 1 d . . . . .
O2 O 0.27571(14) 0.98264(10) 0.11196(11) 0.0260(3) Uani 1 1 d . . . . .
O3 O 0.32254(17) 0.81928(13) 0.26804(13) 0.0420(4) Uani 1 1 d . . . . .
O4 O 0.45221(17) 0.81168(13) 0.40628(13) 0.0429(4) Uani 1 1 d . . . . .
O5 O 0.38297(16) 0.67573(12) 0.33271(13) 0.0383(4) Uani 1 1 d . . . . .
N1 N 0.21095(16) 1.04305(13) 0.39202(13) 0.0270(3) Uani 1 1 d . . . . .
N2 N 0.40509(15) 1.09138(12) 0.27103(12) 0.0248(3) Uani 1 1 d . . . . .
N3 N 0.38615(16) 0.76885(14) 0.33519(13) 0.0296(4) Uani 1 1 d . . . . .
C1 C 0.01806(17) 0.91238(13) 0.14657(14) 0.0206(3) Uani 1 1 d . . . . .
C2 C -0.11001(18) 0.87050(14) 0.15226(15) 0.0238(4) Uani 1 1 d . . . . .
C3 C -0.1911(2) 0.82304(16) 0.07968(19) 0.0349(5) Uani 1 1 d . . . . .
H3 H -0.1730 0.8136 0.0119 0.042 Uiso 1 1 calc R U . . .
C4 C -0.3054(2) 0.78951(19) 0.1175(2) 0.0443(6) Uani 1 1 d . . . . .
H4 H -0.3723 0.7550 0.0777 0.053 Uiso 1 1 calc R U . . .
C5 C -0.3089(2) 0.81207(18) 0.2164(2) 0.0418(6) Uani 1 1 d . . . . .
H5 H -0.3780 0.7947 0.2538 0.050 Uiso 1 1 calc R U . . .
C6 C 0.07894(18) 0.89810(14) 0.05798(14) 0.0242(4) Uani 1 1 d . . . . .
H6 H 0.0338 0.8644 0.0021 0.029 Uiso 1 1 calc R U . . .
C7 C 0.20178(18) 0.93167(13) 0.05048(14) 0.0225(4) Uani 1 1 d . . . . .
C8 C 0.2670(2) 0.90088(15) -0.04325(15) 0.0301(4) Uani 1 1 d . . . . .
C9 C 0.1762(2) 0.95124(18) 0.44530(17) 0.0370(5) Uani 1 1 d . . . . .
H9A H 0.1679 0.9669 0.5162 0.055 Uiso 1 1 calc R U . . .
H9B H 0.2436 0.9010 0.4419 0.055 Uiso 1 1 calc R U . . .
H9C H 0.0941 0.9253 0.4129 0.055 Uiso 1 1 calc R U . . .
C10 C 0.1075(2) 1.11747(18) 0.39766(17) 0.0357(5) Uani 1 1 d . . . . .
H10A H 0.0964 1.1304 0.4687 0.054 Uiso 1 1 calc R U . . .
H10B H 0.0268 1.0918 0.3626 0.054 Uiso 1 1 calc R U . . .
H10C H 0.1308 1.1795 0.3654 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3363(2) 1.08059(19) 0.44026(16) 0.0352(5) Uani 1 1 d . . . . .
H11A H 0.3940 1.0238 0.4604 0.042 Uiso 1 1 calc R U . . .
H11B H 0.3231 1.1189 0.5018 0.042 Uiso 1 1 calc R U . . .
C12 C 0.3973(2) 1.14639(18) 0.36698(17) 0.0346(5) Uani 1 1 d . . . . .
H12A H 0.3451 1.2075 0.3536 0.042 Uiso 1 1 calc R U . . .
H12B H 0.4846 1.1663 0.3965 0.042 Uiso 1 1 calc R U . . .
C13 C 0.5120(2) 1.01891(16) 0.27994(19) 0.0346(5) Uani 1 1 d . . . . .
H13A H 0.5938 1.0541 0.2965 0.052 Uiso 1 1 calc R U . . .
H13B H 0.5134 0.9835 0.2156 0.052 Uiso 1 1 calc R U . . .
H13C H 0.4999 0.9710 0.3336 0.052 Uiso 1 1 calc R U . . .
C14 C 0.4279(2) 1.16300(16) 0.19002(17) 0.0323(4) Uani 1 1 d . . . . .
H14A H 0.5136 1.1926 0.2049 0.048 Uiso 1 1 calc R U . . .
H14B H 0.3626 1.2156 0.1866 0.048 Uiso 1 1 calc R U . . .
H14C H 0.4226 1.1281 0.1250 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9215(14) . ?
Cu1 O1 1.9292(14) . ?
Cu1 N2 2.0189(16) . ?
Cu1 N1 2.0306(17) . ?
S1 C5 1.704(3) . ?
S1 C2 1.728(2) . ?
F1 C8 1.313(3) . ?
F2 C8 1.340(3) . ?
F3 C8 1.304(3) . ?
O1 C1 1.269(2) . ?
O2 C7 1.263(2) . ?
O3 N3 1.252(2) . ?
O4 N3 1.248(2) . ?
O5 N3 1.251(2) . ?
N1 C10 1.480(3) . ?
N1 C11 1.482(3) . ?
N1 C9 1.487(3) . ?
N2 C13 1.477(3) . ?
N2 C14 1.483(3) . ?
N2 C12 1.485(3) . ?
C1 C6 1.413(3) . ?
C1 C2 1.462(3) . ?
C2 C3 1.369(3) . ?
C3 C4 1.420(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.354(4) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.542(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.508(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 93.27(6) . . ?
O2 Cu1 N2 90.26(6) . . ?
O1 Cu1 N2 175.49(6) . . ?
O2 Cu1 N1 172.72(7) . . ?
O1 Cu1 N1 89.26(6) . . ?
N2 Cu1 N1 87.57(7) . . ?
C5 S1 C2 91.61(11) . . ?
C1 O1 Cu1 126.64(12) . . ?
C7 O2 Cu1 123.48(12) . . ?
C10 N1 C11 111.36(18) . . ?
C10 N1 C9 108.48(17) . . ?
C11 N1 C9 109.06(17) . . ?
C10 N1 Cu1 109.38(13) . . ?
C11 N1 Cu1 105.75(12) . . ?
C9 N1 Cu1 112.83(13) . . ?
C13 N2 C14 107.71(16) . . ?
C13 N2 C12 111.84(17) . . ?
C14 N2 C12 109.33(16) . . ?
C13 N2 Cu1 109.54(13) . . ?
C14 N2 Cu1 113.46(13) . . ?
C12 N2 Cu1 105.03(12) . . ?
O4 N3 O5 119.44(18) . . ?
O4 N3 O3 119.81(18) . . ?
O5 N3 O3 120.74(18) . . ?
O1 C1 C6 124.86(17) . . ?
O1 C1 C2 115.71(16) . . ?
C6 C1 C2 119.38(17) . . ?
C3 C2 C1 129.90(18) . . ?
C3 C2 S1 111.18(15) . . ?
C1 C2 S1 118.90(15) . . ?
C2 C3 C4 112.2(2) . . ?
C2 C3 H3 123.9 . . ?
C4 C3 H3 123.9 . . ?
C5 C4 C3 112.8(2) . . ?
C5 C4 H4 123.6 . . ?
C3 C4 H4 123.6 . . ?
C4 C5 S1 112.27(17) . . ?
C4 C5 H5 123.9 . . ?
S1 C5 H5 123.9 . . ?
C7 C6 C1 121.77(18) . . ?
C7 C6 H6 119.1 . . ?
C1 C6 H6 119.1 . . ?
O2 C7 C6 129.80(18) . . ?
O2 C7 C8 112.06(17) . . ?
C6 C7 C8 118.07(17) . . ?
F3 C8 F1 108.5(2) . . ?
F3 C8 F2 105.46(18) . . ?
F1 C8 F2 107.7(2) . . ?
F3 C8 C7 112.47(16) . . ?
F1 C8 C7 110.08(17) . . ?
F2 C8 C7 112.37(18) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 109.62(17) . . ?
N1 C11 H11A 109.7 . . ?
C12 C11 H11A 109.7 . . ?
N1 C11 H11B 109.7 . . ?
C12 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N2 C12 C11 109.39(17) . . ?
N2 C12 H12A 109.8 . . ?
C11 C12 H12A 109.8 . . ?
N2 C12 H12B 109.8 . . ?
C11 C12 H12B 109.8 . . ?
H12A C12 H12B 108.2 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 1.6(3) . . . . ?
Cu1 O1 C1 C2 178.94(12) . . . . ?
O1 C1 C2 C3 176.7(2) . . . . ?
C6 C1 C2 C3 -5.8(3) . . . . ?
O1 C1 C2 S1 -5.4(2) . . . . ?
C6 C1 C2 S1 172.14(14) . . . . ?
C5 S1 C2 C3 0.84(18) . . . . ?
C5 S1 C2 C1 -177.47(16) . . . . ?
C1 C2 C3 C4 177.4(2) . . . . ?
S1 C2 C3 C4 -0.7(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 S1 0.5(3) . . . . ?
C2 S1 C5 C4 -0.8(2) . . . . ?
O1 C1 C6 C7 0.5(3) . . . . ?
C2 C1 C6 C7 -176.79(17) . . . . ?
Cu1 O2 C7 C6 5.8(3) . . . . ?
Cu1 O2 C7 C8 -171.16(12) . . . . ?
C1 C6 C7 O2 -4.7(3) . . . . ?
C1 C6 C7 C8 172.13(17) . . . . ?
O2 C7 C8 F3 -33.3(2) . . . . ?
C6 C7 C8 F3 149.36(19) . . . . ?
O2 C7 C8 F1 87.8(2) . . . . ?
C6 C7 C8 F1 -89.5(2) . . . . ?
O2 C7 C8 F2 -152.12(18) . . . . ?
C6 C7 C8 F2 30.5(3) . . . . ?
C10 N1 C11 C12 -82.0(2) . . . . ?
C9 N1 C11 C12 158.30(19) . . . . ?
Cu1 N1 C11 C12 36.7(2) . . . . ?
C13 N2 C12 C11 -77.4(2) . . . . ?
C14 N2 C12 C11 163.40(18) . . . . ?
Cu1 N2 C12 C11 41.3(2) . . . . ?
N1 C11 C12 N2 -54.0(2) . . . . ?

_refine_diff_density_max         0.916
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.072


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
####################################################################### 
# 
# 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_cmpd4_CuTTAbipyCl
_database_code_depnum_ccdc_archive 'CCDC 2056494'
loop_
_audit_author_name
_audit_author_address
'Alexandra Friedrich'
;Julius Maximilians Universitaet Wuerzburg
Germany
;
_audit_update_record             
;
2021-01-15 deposited with the CCDC.	2022-08-02 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12 Cl Cu F3 N2 O2 S'
_chemical_formula_sum            'C18 H12 Cl Cu F3 N2 O2 S'
_chemical_formula_weight         476.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   13.023(6)
_cell_length_b                   8.377(4)
_cell_length_c                   17.040(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.899(13)
_cell_angle_gamma                90
_cell_volume                     1778.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.91

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.779
_exptl_crystal_F_000             956
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    1.543
_shelx_estimated_absorpt_T_min   0.512
_shelx_estimated_absorpt_T_max   0.577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6300
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SadAbs 2014/5 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode (Nonius FR-591)'
_diffrn_measurement_device_type  'Bruker X8-APEX II'
_diffrn_detector                 'CCD area detector (Apex2)'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.333
_diffrn_reflns_number            64883
_diffrn_reflns_av_unetI/netI     0.0086
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.634
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3500
_reflns_number_gt                3350
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.34A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.34A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
 The displacement parameters of atoms XXX and XXX of the residue YYY
 were constrained to the same value. 
 The displacement parameters of atoms XXX and XXX of the residue YYY
 were restrained to the same value with similarity restraint SIMU. 
 The distances between atoms XXX and YYY were restrained during
 refinement to the same value. 
 The Uii displacement parameters of atoms XXX and YYY were restrained with 
 ISOR keyword to approximate isotropic behavior. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0275P)²+2.7644P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   iterative
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3500
_refine_ls_number_parameters     283
_refine_ls_number_restraints     58
_refine_ls_R_factor_all          0.0261
_refine_ls_R_factor_gt           0.0249
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0618
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.182
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.24073(2) 0.53148(3) 0.43355(2) 0.01129(8) Uani 1 1 d . . . . .
Cl1 Cl 0.13392(3) 0.76737(5) 0.37132(3) 0.01487(10) Uani 1 1 d . . . . .
F1A F 0.3476(4) 0.2813(4) 0.2317(2) 0.0243(7) Uani 0.772(11) 1 d . U P A 3
F2A F 0.3059(4) 0.5139(5) 0.17732(19) 0.0315(8) Uani 0.772(11) 1 d . U P A 3
F3A F 0.4718(3) 0.4490(6) 0.2304(2) 0.0317(8) Uani 0.772(11) 1 d . U P A 3
F2B F 0.2794(9) 0.4688(15) 0.1807(7) 0.0273(15) Uani 0.228(11) 1 d . U P A 4
F3B F 0.4474(10) 0.5053(16) 0.2161(6) 0.0314(14) Uani 0.228(11) 1 d . U P A 4
F1B F 0.3820(10) 0.2893(19) 0.2401(9) 0.0266(15) Uani 0.228(11) 1 d . U P A 4
O1 O 0.27917(10) 0.46242(16) 0.33661(8) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.37753(10) 0.63932(16) 0.47883(8) 0.0150(3) Uani 1 1 d . . . . .
N1 N 0.12423(12) 0.36781(18) 0.41355(9) 0.0118(3) Uani 1 1 d . . . . .
N2 N 0.21794(13) 0.52988(18) 0.54524(9) 0.0127(3) Uani 1 1 d . . . . .
C1 C 0.37295(16) 0.4377(2) 0.24026(12) 0.0161(4) Uani 1 1 d . . . . .
C2 C 0.36549(15) 0.5037(2) 0.32198(11) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.44830(15) 0.5974(2) 0.36702(11) 0.0151(4) Uani 1 1 d . . . . .
H3 H 0.506186 0.620245 0.345381 0.018 Uiso 1 1 calc R U . . .
C4 C 0.45064(14) 0.6613(2) 0.44473(11) 0.0129(4) Uani 1 1 d . . . . .
C5 C 0.54000(14) 0.7600(2) 0.49030(10) 0.0146(4) Uani 1 1 d D . . . .
C7 C 0.69816(16) 0.9175(2) 0.52801(14) 0.0275(5) Uani 1 1 d D . . . .
H7A H 0.763078 0.965465 0.525160 0.033 Uiso 0.7855(16) 1 calc R U P B 1
H7B H 0.764102 0.967216 0.529049 0.033 Uiso 0.2145(16) 1 calc R U P B 2
C8 C 0.65037(17) 0.9431(2) 0.58767(14) 0.0271(5) Uani 1 1 d D . . . .
H8A H 0.680481 1.011906 0.632812 0.033 Uiso 0.7855(16) 1 calc R U P B 1
H8B H 0.674524 1.010635 0.634186 0.033 Uiso 0.2145(16) 1 calc R U P B 2
C9 C 0.08215(15) 0.2894(2) 0.34312(11) 0.0145(4) Uani 1 1 d . . . . .
H9 H 0.107231 0.313377 0.297378 0.017 Uiso 1 1 calc R U . . .
C10 C 0.00323(15) 0.1745(2) 0.33468(12) 0.0168(4) Uani 1 1 d . . . . .
H10 H -0.025187 0.119756 0.284168 0.020 Uiso 1 1 calc R U . . .
C11 C -0.03326(15) 0.1411(2) 0.40141(12) 0.0169(4) Uani 1 1 d . . . . .
H11 H -0.086984 0.062209 0.397250 0.020 Uiso 1 1 calc R U . . .
C12 C 0.00874(15) 0.2231(2) 0.47448(11) 0.0145(4) Uani 1 1 d . . . . .
H12 H -0.016321 0.202560 0.520592 0.017 Uiso 1 1 calc R U . . .
C13 C 0.08824(14) 0.3359(2) 0.47860(11) 0.0115(3) Uani 1 1 d . . . . .
C14 C 0.14078(14) 0.4293(2) 0.55326(11) 0.0117(3) Uani 1 1 d . . . . .
C15 C 0.11383(15) 0.4171(2) 0.62618(11) 0.0142(4) Uani 1 1 d . . . . .
H15 H 0.058885 0.346160 0.630660 0.017 Uiso 1 1 calc R U . . .
C16 C 0.16884(16) 0.5105(2) 0.69236(12) 0.0168(4) Uani 1 1 d . . . . .
H16 H 0.151778 0.504590 0.742827 0.020 Uiso 1 1 calc R U . . .
C17 C 0.24876(16) 0.6125(2) 0.68412(11) 0.0176(4) Uani 1 1 d . . . . .
H17 H 0.287730 0.676533 0.728888 0.021 Uiso 1 1 calc R U . . .
C18 C 0.27090(15) 0.6193(2) 0.60942(11) 0.0166(4) Uani 1 1 d . . . . .
H18 H 0.325375 0.689717 0.603528 0.020 Uiso 1 1 calc R U . . .
S1A S 0.53814(5) 0.84836(10) 0.57705(4) 0.01225(15) Uani 0.7855(16) 1 d D U P B
1
C6A C 0.6367(3) 0.8094(5) 0.4715(2) 0.01225(15) Uani 0.7855(16) 1 d D . P B 1
H6A H 0.656235 0.771881 0.425222 0.015 Uiso 0.7855(16) 1 calc R U P B 1
S1B S 0.6404(3) 0.8044(4) 0.45893(17) 0.01225(15) Uani 0.2145(16) 1 d D U P B 2
C6B C 0.5575(8) 0.8483(16) 0.5660(6) 0.01225(15) Uani 0.2145(16) 1 d D U P B 2
H6B H 0.509639 0.842572 0.598656 0.015 Uiso 0.2145(16) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9458(15) . ?
Cu1 O1 1.9480(15) . ?
Cu1 N1 1.9993(17) . ?
Cu1 N2 2.0096(17) . ?
Cu1 Cl1 2.4712(10) . ?
F1A C1 1.348(4) . ?
F2A C1 1.332(4) . ?
F3A C1 1.349(3) . ?
F2B C1 1.365(11) . ?
F3B C1 1.289(10) . ?
F1B C1 1.249(16) . ?
O1 C2 1.268(2) . ?
O2 C4 1.265(2) . ?
N1 C9 1.338(2) . ?
N1 C13 1.350(2) . ?
N2 C18 1.340(2) . ?
N2 C14 1.348(2) . ?
C1 C2 1.527(3) . ?
C2 C3 1.373(3) . ?
C3 C4 1.421(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.454(3) . ?
C5 C6B 1.446(6) . ?
C5 C6A 1.447(4) . ?
C5 S1B 1.593(3) . ?
C5 S1A 1.6599(19) . ?
C7 C8 1.355(4) . ?
C7 C6A 1.393(4) . ?
C7 S1B 1.528(3) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C8 C6B 1.403(5) . ?
C8 S1A 1.626(2) . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?
C9 C10 1.385(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.481(3) . ?
C14 C15 1.390(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.386(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C6A H6A 0.9500 . ?
C6B H6B 0.9500 . ?

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 O1 92.45(6) . . ?
O2 Cu1 N1 161.43(6) . . ?
O1 Cu1 N1 91.21(6) . . ?
O2 Cu1 N2 89.87(6) . . ?
O1 Cu1 N2 161.11(6) . . ?
N1 Cu1 N2 80.98(6) . . ?
O2 Cu1 Cl1 97.77(5) . . ?
O1 Cu1 Cl1 97.18(5) . . ?
N1 Cu1 Cl1 99.83(6) . . ?
N2 Cu1 Cl1 101.08(5) . . ?
C2 O1 Cu1 123.14(12) . . ?
C4 O2 Cu1 127.60(12) . . ?
C9 N1 C13 119.34(16) . . ?
C9 N1 Cu1 125.61(13) . . ?
C13 N1 Cu1 115.04(12) . . ?
C18 N2 C14 119.26(16) . . ?
C18 N2 Cu1 125.92(13) . . ?
C14 N2 Cu1 114.82(12) . . ?
F1B C1 F3B 110.9(7) . . ?
F2A C1 F1A 107.2(2) . . ?
F2A C1 F3A 106.9(2) . . ?
F1A C1 F3A 105.5(2) . . ?
F1B C1 F2B 104.7(7) . . ?
F3B C1 F2B 105.7(6) . . ?
F1B C1 C2 113.1(7) . . ?
F3B C1 C2 112.7(5) . . ?
F2A C1 C2 111.1(2) . . ?
F1A C1 C2 111.8(2) . . ?
F3A C1 C2 113.83(19) . . ?
F2B C1 C2 109.2(5) . . ?
O1 C2 C3 130.01(18) . . ?
O1 C2 C1 112.04(16) . . ?
C3 C2 C1 117.94(17) . . ?
C2 C3 C4 122.47(17) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
O2 C4 C3 123.94(17) . . ?
O2 C4 C5 115.46(16) . . ?
C3 C4 C5 120.60(16) . . ?
C6B C5 C4 131.4(3) . . ?
C6A C5 C4 131.08(19) . . ?
C6B C5 S1B 104.3(3) . . ?
C4 C5 S1B 124.10(17) . . ?
C6A C5 S1A 107.97(17) . . ?
C4 C5 S1A 120.83(13) . . ?
C8 C7 C6A 108.9(2) . . ?
C8 C7 S1B 116.45(19) . . ?
C8 C7 H7A 125.5 . . ?
C6A C7 H7A 125.5 . . ?
C8 C7 H7B 121.8 . . ?
S1B C7 H7B 121.8 . . ?
C7 C8 C6B 105.2(3) . . ?
C7 C8 S1A 115.68(16) . . ?
C7 C8 H8A 122.2 . . ?
S1A C8 H8A 122.2 . . ?
C7 C8 H8B 127.4 . . ?
C6B C8 H8B 127.4 . . ?
N1 C9 C10 122.18(17) . . ?
N1 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C11 C10 C9 118.50(17) . . ?
C11 C10 H10 120.7 . . ?
C9 C10 H10 120.7 . . ?
C10 C11 C12 119.87(18) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.42(18) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
N1 C13 C12 121.68(17) . . ?
N1 C13 C14 114.63(16) . . ?
C12 C13 C14 123.69(17) . . ?
N2 C14 C15 121.74(17) . . ?
N2 C14 C13 114.52(16) . . ?
C15 C14 C13 123.74(17) . . ?
C16 C15 C14 118.67(18) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C17 C16 C15 119.40(18) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C16 C17 C18 118.81(18) . . ?
C16 C17 H17 120.6 . . ?
C18 C17 H17 120.6 . . ?
N2 C18 C17 122.11(18) . . ?
N2 C18 H18 118.9 . . ?
C17 C18 H18 118.9 . . ?
C8 S1A C5 94.09(11) . . ?
C7 C6A C5 113.3(3) . . ?
C7 C6A H6A 123.4 . . ?
C5 C6A H6A 123.4 . . ?
C7 S1B C5 98.90(16) . . ?
C8 C6B C5 115.1(5) . . ?
C8 C6B H6B 122.4 . . ?
C5 C6B H6B 122.4 . . ?

_refine_diff_density_max         0.710
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.064


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol/diethylether'
