# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_20201109-czf-swy-l26
_database_code_depnum_ccdc_archive 'CCDC 2115672'
loop_
_audit_author_name
_audit_author_address
'Wen Ying Shen'
;Guangxi Normal University
China
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H24 Cl4 Cu F2 N4 O2'
_chemical_formula_sum            'C44 H24 Cl4 Cu F2 N4 O2'
_chemical_formula_weight         884.01
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C84 H44 Cl8 Cu2 F4 N12 O4 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   10.06330(10)
_cell_length_b                   19.92460(10)
_cell_length_c                   10.12960(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.2100(10)
_cell_angle_gamma                90
_cell_volume                     1906.01(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    13650
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      77.7510
_cell_measurement_theta_min      4.4290
_shelx_estimated_absorpt_T_max   0.655
_shelx_estimated_absorpt_T_min   0.596
_exptl_absorpt_coefficient_mu    3.851
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             894
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0290
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17093
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.030
_diffrn_reflns_theta_min         4.438
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     97.00 178.00   0.50    0.60    --  110.00  45.00   0.00  162
  2  ω    122.00 177.00   0.50    0.60    --  110.00  45.00  30.00  110
  3  ω     95.00 121.00   0.50    0.60    --  110.00  15.00 150.00   52
  4  ω    103.00 178.00   0.50    0.60    --  110.00  45.00 -30.00  150
  5  ω    100.00 133.00   0.50    0.60    --  110.00  77.00-180.00   66
  6  ω    -26.00  28.00   0.50    0.16    --  -47.12  19.00-120.00  108
  7  ω    -69.00 -19.00   0.50    0.16    --  -47.12 102.00  45.00  100
  8  ω    -72.00 -47.00   0.50    0.60    --  -88.50 102.00  45.00   50
  9  ω      8.00  82.00   0.50    0.16    --   47.12-102.00 -58.00  148
 10  ω     39.00 106.00   0.50    0.60    --  110.00-102.00 -58.00  134
 11  ω     51.00 101.00   0.50    0.60    --  110.00 -94.00 -30.00  100
 12  ω     44.00  70.00   0.50    0.60    --  110.00 -94.00  30.00   52
 13  ω     73.00  99.00   0.50    0.60    --  110.00 -94.00  30.00   52
 14  ω     57.00  91.00   0.50    0.60    --  110.00 -94.00   0.00   68
 15  ω     74.00  99.00   0.50    0.60    --  110.00 -77.00 -30.00   50
 16  ω     56.00  82.00   0.50    0.60    --  110.00 -77.00  30.00   52
 17  ω     38.00  71.00   0.50    0.60    --  110.00 -61.00   0.00   66
 18  ω     40.00  69.00   0.50    0.60    --  110.00 -61.00  60.00   58
 19  ω     46.00  72.00   0.50    0.60    --  110.00 -77.00 -30.00   52
 20  ω     78.00 104.00   0.50    0.60    --  110.00 -77.00 -90.00   52
 21  ω     38.00  70.00   0.50    0.60    --  110.00 -61.00-150.00   64
 22  ω     42.00  68.00   0.50    0.60    --  110.00 -61.00-180.00   52
 23  ω     40.00  70.00   0.50    0.60    --  110.00 -61.00  30.00   60
 24  ω     43.00  71.00   0.50    0.60    --  110.00 -61.00  90.00   56
 25  ω     38.00  71.00   0.50    0.60    --  110.00 -61.00 150.00   66
 26  ω    -25.00  20.00   0.50    0.16    --   47.12 -19.00  30.00   90
 27  ω    103.00 154.00   0.50    0.60    --  110.00 125.00  60.00  102
 28  ω    109.00 144.00   0.50    0.60    --  110.00 102.00  45.00   70
 29  ω    -80.00 -54.00   0.50    0.16    --  -47.12 -57.00   0.00   52
 30  ω   -149.00 -98.00   0.50    0.60    --  -88.50-102.00 -58.00  102
 31  ω   -118.00 -84.00   0.50    0.16    --  -47.12-125.00   0.00   68
 32  ω   -117.00 -74.00   0.50    0.16    --  -47.12-125.00  30.00   86
 33  ω   -118.00 -88.00   0.50    0.16    --  -47.12-125.00 150.00   60
 34  ω     94.00 120.00   0.50    0.16    --   46.87  77.00-180.00   52
 35  ω     54.00  80.00   0.50    0.60    --  110.00 -77.00 120.00   52
 36  ω     44.00  70.00   0.50    0.60    --  110.00 -61.00  60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0496377000
_diffrn_orient_matrix_UB_12      -0.0736514000
_diffrn_orient_matrix_UB_13      0.0165175000
_diffrn_orient_matrix_UB_21      0.0547590000
_diffrn_orient_matrix_UB_22      0.0085169000
_diffrn_orient_matrix_UB_23      -0.1234466000
_diffrn_orient_matrix_UB_31      0.1454132000
_diffrn_orient_matrix_UB_32      0.0220003000
_diffrn_orient_matrix_UB_33      0.1036676000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3735
_reflns_number_total             3988
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00075(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         3988
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.7255P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0956
_refine_ls_wR_factor_ref         0.0968
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C22(H22), C7(H7), C6(H6), C5(H5), C11(H11), C4(H4), C20(H20),
 C19(H19), C14(H14), C12(H12), C13(H13)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.02860(12) Uani 1 2 d S . P . .
Cl1 Cl 0.65450(6) 0.71160(2) 0.70513(5) 0.05213(15) Uani 1 1 d . . . . .
Cl2 Cl 0.80298(7) 0.72342(3) 1.03460(6) 0.06558(18) Uani 1 1 d . . . . .
O1 O 0.54723(13) 0.57914(6) 0.61333(12) 0.0349(3) Uani 1 1 d . . . . .
F1 F 0.24832(14) 0.51871(6) 0.69079(12) 0.0553(3) Uani 1 1 d . . . . .
N1 N 0.47847(14) 0.44882(6) 0.65770(14) 0.0306(3) Uani 1 1 d . . . . .
N2 N 0.15894(14) 0.34456(7) 0.52158(16) 0.0362(3) Uani 1 1 d . . . . .
C16 C 0.60368(16) 0.58206(8) 0.74835(16) 0.0308(3) Uani 1 1 d . . . . .
C1 C 0.39330(16) 0.38966(8) 0.62966(16) 0.0305(3) Uani 1 1 d . . . . .
C9 C 0.24635(17) 0.39571(8) 0.54636(17) 0.0315(3) Uani 1 1 d . . . . .
C10 C 0.18827(16) 0.46035(8) 0.47621(18) 0.0341(3) Uani 1 1 d . . . . .
C17 C 0.66357(17) 0.64379(8) 0.81355(18) 0.0352(3) Uani 1 1 d . . . . .
C2 C 0.44759(18) 0.32810(8) 0.67704(18) 0.0363(4) Uani 1 1 d . . . . .
H2 H 0.543792 0.323053 0.727002 0.044 Uiso 1 1 calc R U . . .
C21 C 0.61035(17) 0.52708(9) 0.83977(17) 0.0338(3) Uani 1 1 d . . . . .
C22 C 0.53934(17) 0.46508(8) 0.78777(17) 0.0337(3) Uani 1 1 d . . . . .
H22 H 0.536983 0.433495 0.854519 0.040 Uiso 1 1 calc R U . . .
C8 C 0.21103(18) 0.28305(8) 0.57477(18) 0.0353(3) Uani 1 1 d . . . . .
C3 C 0.35626(19) 0.27186(8) 0.64953(18) 0.0363(4) Uani 1 1 d . . . . .
C15 C 0.19572(19) 0.52026(9) 0.5480(2) 0.0405(4) Uani 1 1 d . . . . .
C18 C 0.72736(18) 0.64878(10) 0.9576(2) 0.0409(4) Uani 1 1 d . . . . .
C7 C 0.1152(2) 0.22866(10) 0.5527(2) 0.0447(4) Uani 1 1 d . . . . .
H7 H 0.018931 0.235592 0.506118 0.054 Uiso 1 1 calc R U . . .
C6 C 0.1641(2) 0.16610(10) 0.5997(2) 0.0503(5) Uani 1 1 d . . . . .
H6 H 0.100466 0.130734 0.586268 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3095(2) 0.15449(10) 0.6682(2) 0.0519(5) Uani 1 1 d . . . . .
H5 H 0.341559 0.111239 0.696336 0.062 Uiso 1 1 calc R U . . .
C11 C 0.12578(19) 0.46287(10) 0.3303(2) 0.0433(4) Uani 1 1 d . . . . .
H11 H 0.115253 0.423589 0.278084 0.052 Uiso 1 1 calc R U . . .
C4 C 0.4042(2) 0.20634(9) 0.6937(2) 0.0474(4) Uani 1 1 d . . . . .
H4 H 0.500102 0.198365 0.740169 0.057 Uiso 1 1 calc R U . . .
C20 C 0.6748(2) 0.53465(10) 0.98637(18) 0.0434(4) Uani 1 1 d . . . . .
H20 H 0.677371 0.498175 1.044481 0.052 Uiso 1 1 calc R U . . .
C19 C 0.7336(2) 0.59395(11) 1.04556(19) 0.0475(4) Uani 1 1 d . . . . .
H19 H 0.777016 0.597817 1.142518 0.057 Uiso 1 1 calc R U . . .
C14 C 0.1503(2) 0.58073(10) 0.4827(3) 0.0539(5) Uani 1 1 d . . . . .
H14 H 0.158407 0.619940 0.534689 0.065 Uiso 1 1 calc R U . . .
C12 C 0.0792(2) 0.52314(13) 0.2622(2) 0.0567(5) Uani 1 1 d . . . . .
H12 H 0.038530 0.524092 0.164665 0.068 Uiso 1 1 calc R U . . .
C13 C 0.0925(3) 0.58162(12) 0.3377(3) 0.0605(6) Uani 1 1 d . . . . .
H13 H 0.062344 0.621994 0.290890 0.073 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 1.9112(11) 3_666 ?
Cu1 O1 1.9113(11) . ?
Cu1 N1 1.9692(13) 3_666 ?
Cu1 N1 1.9692(13) . ?
Cl1 C17 1.7235(18) . ?
Cl2 C18 1.7291(18) . ?
O1 C16 1.2884(19) . ?
F1 C15 1.358(2) . ?
N1 C1 1.4270(19) . ?
N1 C22 1.288(2) . ?
N2 C9 1.313(2) . ?
N2 C8 1.368(2) . ?
C16 C17 1.427(2) . ?
C16 C21 1.421(2) . ?
C1 C9 1.432(2) . ?
C1 C2 1.361(2) . ?
C9 C10 1.489(2) . ?
C10 C15 1.386(3) . ?
C10 C11 1.393(3) . ?
C17 C18 1.379(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.415(2) . ?
C21 C22 1.433(2) . ?
C21 C20 1.408(2) . ?
C22 H22 0.9300 . ?
C8 C3 1.412(2) . ?
C8 C7 1.416(2) . ?
C3 C4 1.410(2) . ?
C15 C14 1.375(3) . ?
C18 C19 1.398(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.364(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.405(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.368(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C4 H4 0.9300 . ?
C20 H20 0.9300 . ?
C20 C19 1.364(3) . ?
C19 H19 0.9300 . ?
C14 H14 0.9300 . ?
C14 C13 1.380(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.375(4) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 3_666 . ?
O1 Cu1 N1 89.19(5) . 3_666 ?
O1 Cu1 N1 90.81(5) . . ?
O1 Cu1 N1 90.81(5) 3_666 3_666 ?
O1 Cu1 N1 89.18(5) 3_666 . ?
N1 Cu1 N1 180.0 3_666 . ?
C16 O1 Cu1 127.00(10) . . ?
C1 N1 Cu1 119.55(10) . . ?
C22 N1 Cu1 123.56(11) . . ?
C22 N1 C1 116.88(13) . . ?
C9 N2 C8 118.68(14) . . ?
O1 C16 C17 119.40(15) . . ?
O1 C16 C21 124.14(14) . . ?
C21 C16 C17 116.45(14) . . ?
N1 C1 C9 118.34(14) . . ?
C2 C1 N1 122.27(14) . . ?
C2 C1 C9 119.38(14) . . ?
N2 C9 C1 122.32(15) . . ?
N2 C9 C10 116.98(14) . . ?
C1 C9 C10 120.60(14) . . ?
C15 C10 C9 123.57(16) . . ?
C15 C10 C11 116.65(16) . . ?
C11 C10 C9 119.75(15) . . ?
C16 C17 Cl1 117.37(13) . . ?
C18 C17 Cl1 121.35(13) . . ?
C18 C17 C16 121.28(16) . . ?
C1 C2 H2 120.3 . . ?
C1 C2 C3 119.35(15) . . ?
C3 C2 H2 120.3 . . ?
C16 C21 C22 121.31(14) . . ?
C20 C21 C16 120.36(15) . . ?
C20 C21 C22 118.00(16) . . ?
N1 C22 C21 126.40(15) . . ?
N1 C22 H22 116.8 . . ?
C21 C22 H22 116.8 . . ?
N2 C8 C3 122.50(15) . . ?
N2 C8 C7 118.43(16) . . ?
C3 C8 C7 119.07(16) . . ?
C8 C3 C2 117.53(15) . . ?
C4 C3 C2 122.90(17) . . ?
C4 C3 C8 119.57(16) . . ?
F1 C15 C10 118.02(16) . . ?
F1 C15 C14 118.38(18) . . ?
C14 C15 C10 123.59(19) . . ?
C17 C18 Cl2 120.71(15) . . ?
C17 C18 C19 121.34(16) . . ?
C19 C18 Cl2 117.94(14) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.04(18) . . ?
C6 C7 H7 120.0 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.74(17) . . ?
C5 C6 H6 119.6 . . ?
C6 C5 H5 119.7 . . ?
C4 C5 C6 120.51(18) . . ?
C4 C5 H5 119.7 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.75(19) . . ?
C12 C11 H11 119.6 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.97(19) . . ?
C5 C4 H4 120.0 . . ?
C21 C20 H20 119.1 . . ?
C19 C20 C21 121.88(18) . . ?
C19 C20 H20 119.1 . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.66(16) . . ?
C20 C19 H19 120.7 . . ?
C15 C14 H14 120.9 . . ?
C15 C14 C13 118.1(2) . . ?
C13 C14 H14 120.9 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C14 C13 H13 119.8 . . ?
C12 C13 C14 120.35(19) . . ?
C12 C13 H13 119.8 . . ?

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 C16 C17 164.68(11) . . . . ?
Cu1 O1 C16 C21 -15.7(2) . . . . ?
Cu1 N1 C1 C9 -60.68(18) . . . . ?
Cu1 N1 C1 C2 118.08(15) . . . . ?
Cu1 N1 C22 C21 11.6(2) . . . . ?
Cl1 C17 C18 Cl2 -0.9(2) . . . . ?
Cl1 C17 C18 C19 179.44(15) . . . . ?
Cl2 C18 C19 C20 -179.81(15) . . . . ?
O1 C16 C17 Cl1 0.6(2) . . . . ?
O1 C16 C17 C18 -178.79(16) . . . . ?
O1 C16 C21 C22 -7.1(3) . . . . ?
O1 C16 C21 C20 179.66(16) . . . . ?
F1 C15 C14 C13 -177.8(2) . . . . ?
N1 C1 C9 N2 -176.43(15) . . . . ?
N1 C1 C9 C10 7.5(2) . . . . ?
N1 C1 C2 C3 177.85(15) . . . . ?
N2 C9 C10 C15 125.31(18) . . . . ?
N2 C9 C10 C11 -56.5(2) . . . . ?
N2 C8 C3 C2 4.3(3) . . . . ?
N2 C8 C3 C4 -175.95(18) . . . . ?
N2 C8 C7 C6 177.59(18) . . . . ?
C16 C17 C18 Cl2 178.51(13) . . . . ?
C16 C17 C18 C19 -1.2(3) . . . . ?
C16 C21 C22 N1 8.7(3) . . . . ?
C16 C21 C20 C19 -0.6(3) . . . . ?
C1 N1 C22 C21 -169.42(16) . . . . ?
C1 C9 C10 C15 -58.4(2) . . . . ?
C1 C9 C10 C11 119.81(18) . . . . ?
C1 C2 C3 C8 -0.8(3) . . . . ?
C1 C2 C3 C4 179.38(18) . . . . ?
C9 N2 C8 C3 -3.1(3) . . . . ?
C9 N2 C8 C7 177.41(16) . . . . ?
C9 C1 C2 C3 -3.4(3) . . . . ?
C9 C10 C15 F1 -5.6(3) . . . . ?
C9 C10 C15 C14 175.67(18) . . . . ?
C9 C10 C11 C12 -175.91(18) . . . . ?
C10 C15 C14 C13 0.9(3) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C17 C16 C21 C22 172.60(15) . . . . ?
C17 C16 C21 C20 -0.7(2) . . . . ?
C17 C18 C19 C20 -0.1(3) . . . . ?
C2 C1 C9 N2 4.8(2) . . . . ?
C2 C1 C9 C10 -171.30(16) . . . . ?
C2 C3 C4 C5 177.61(19) . . . . ?
C21 C16 C17 Cl1 -179.07(12) . . . . ?
C21 C16 C17 C18 1.5(2) . . . . ?
C21 C20 C19 C18 1.0(3) . . . . ?
C22 N1 C1 C9 120.32(17) . . . . ?
C22 N1 C1 C2 -60.9(2) . . . . ?
C22 C21 C20 C19 -174.07(18) . . . . ?
C8 N2 C9 C1 -1.5(2) . . . . ?
C8 N2 C9 C10 174.75(15) . . . . ?
C8 C3 C4 C5 -2.2(3) . . . . ?
C8 C7 C6 C5 -1.1(3) . . . . ?
C3 C8 C7 C6 -1.9(3) . . . . ?
C15 C10 C11 C12 2.4(3) . . . . ?
C15 C14 C13 C12 1.0(4) . . . . ?
C7 C8 C3 C2 -176.25(17) . . . . ?
C7 C8 C3 C4 3.5(3) . . . . ?
C7 C6 C5 C4 2.5(3) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C11 C10 C15 F1 176.13(16) . . . . ?
C11 C10 C15 C14 -2.6(3) . . . . ?
C11 C12 C13 C14 -1.1(4) . . . . ?
C20 C21 C22 N1 -177.90(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.316
_oxdiff_exptl_absorpt_empirical_full_min 0.621
####################################################################### 
# 
# 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_20200428-czf-swy-l12cuaaa
_database_code_depnum_ccdc_archive 'CCDC 2115673'
loop_
_audit_author_name
_audit_author_address
'Wen Ying Shen'
;Guangxi Normal University
China
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-07
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C44 H24 Cl4 Cu F2 N4 O2'
_chemical_formula_sum            'C44 H24 Cl4 Cu F2 N4 O2'
_chemical_formula_weight         884.01
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.6802(6)
_cell_length_b                   9.9152(2)
_cell_length_c                   20.2125(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.951(3)
_cell_angle_gamma                90
_cell_volume                     3929.39(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4569
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0980
_cell_measurement_theta_min      3.7710
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    0.881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.494
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1788
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            13338
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.972
_diffrn_reflns_theta_min         3.734
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  68.00   1.00    5.00    --   17.77-114.00 -43.00   75
  2  ω    -92.00   6.00   1.00    5.00    --  -19.57 -38.00-120.00   98
  3  ω    -80.00   1.00   1.00    5.00    --  -19.57 -57.00 -90.00   81
  4  ω    -90.00  -3.00   1.00    5.00    --  -19.57 -38.00 -30.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0018681000
_diffrn_orient_matrix_UB_12      0.0141094000
_diffrn_orient_matrix_UB_13      -0.0345168000
_diffrn_orient_matrix_UB_21      -0.0361388000
_diffrn_orient_matrix_UB_22      0.0009107000
_diffrn_orient_matrix_UB_23      -0.0011440000
_diffrn_orient_matrix_UB_31      0.0008115000
_diffrn_orient_matrix_UB_32      0.0700789000
_diffrn_orient_matrix_UB_33      0.0069617000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3658
_reflns_number_total             4613
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4613
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0512
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+3.1379P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0899
_refine_ls_wR_factor_ref         0.0999
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C20(H20), C18(H18), C2(H2), C22(H22), C11(H11), C4(H4), C5(H5), C6(H6),
 C12(H12), C7(H7), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.250000 0.250000 0.500000 0.02968(11) Uani 1 2 d S . P . .
Cl1 Cl 0.39199(3) 0.36658(7) 0.33016(3) 0.05705(18) Uani 1 1 d . . . . .
Cl2 Cl 0.54169(3) -0.08171(8) 0.37523(4) 0.0723(2) Uani 1 1 d . . . . .
O1 O 0.31229(7) 0.26131(14) 0.43387(7) 0.0393(3) Uani 1 1 d . . . . .
N1 N 0.22145(8) 0.43918(16) 0.47877(8) 0.0326(4) Uani 1 1 d . . . . .
N2 N 0.35940(9) 0.64240(18) 0.41579(9) 0.0390(4) Uani 1 1 d . . . . .
C1 C 0.25763(10) 0.51829(19) 0.43340(10) 0.0329(4) Uani 1 1 d . . . . .
F1 F 0.26869(8) 0.65307(18) 0.57220(8) 0.0735(5) Uani 1 1 d . . . . .
C9 C 0.32355(10) 0.56940(19) 0.45495(10) 0.0337(4) Uani 1 1 d . . . . .
C3 C 0.26706(11) 0.6214(2) 0.32777(11) 0.0389(5) Uani 1 1 d . . . . .
C16 C 0.36212(10) 0.1822(2) 0.42222(10) 0.0338(4) Uani 1 1 d . . . . .
C20 C 0.43102(11) -0.0234(2) 0.43929(12) 0.0460(5) Uani 1 1 d . . . . .
H20 H 0.438863 -0.105653 0.460754 0.055 Uiso 1 1 calc R U . . .
C8 C 0.33213(11) 0.6671(2) 0.35235(11) 0.0395(5) Uani 1 1 d . . . . .
C10 C 0.35606(11) 0.5418(2) 0.52238(11) 0.0382(5) Uani 1 1 d . . . . .
C18 C 0.46191(11) 0.1398(3) 0.36036(12) 0.0483(6) Uani 1 1 d . . . . .
H18 H 0.491168 0.167951 0.329345 0.058 Uiso 1 1 calc R U . . .
C19 C 0.47334(11) 0.0187(2) 0.39364(13) 0.0484(6) Uani 1 1 d . . . . .
C2 C 0.23021(10) 0.5450(2) 0.37145(11) 0.0386(5) Uani 1 1 d . . . . .
H2 H 0.186907 0.513088 0.357445 0.046 Uiso 1 1 calc R U . . .
C21 C 0.37533(10) 0.0572(2) 0.45408(11) 0.0370(5) Uani 1 1 d . . . . .
C22 C 0.33143(10) 0.0037(2) 0.50057(11) 0.0370(5) Uani 1 1 d . . . . .
H22 H 0.342321 -0.081481 0.517633 0.044 Uiso 1 1 calc R U . . .
C15 C 0.32854(13) 0.5855(3) 0.57931(12) 0.0499(6) Uani 1 1 d . . . . .
C17 C 0.40707(11) 0.2179(2) 0.37350(11) 0.0405(5) Uani 1 1 d . . . . .
C11 C 0.41819(12) 0.4750(3) 0.53111(13) 0.0517(6) Uani 1 1 d . . . . .
H11 H 0.438496 0.443830 0.494155 0.062 Uiso 1 1 calc R U . . .
C4 C 0.24255(14) 0.6514(3) 0.26182(12) 0.0554(6) Uani 1 1 d . . . . .
H4 H 0.199675 0.621203 0.245271 0.067 Uiso 1 1 calc R U . . .
C5 C 0.28140(16) 0.7244(3) 0.22228(14) 0.0654(8) Uani 1 1 d . . . . .
H5 H 0.264822 0.745015 0.178977 0.079 Uiso 1 1 calc R U . . .
C6 C 0.34595(16) 0.7682(3) 0.24668(15) 0.0658(8) Uani 1 1 d . . . . .
H6 H 0.372315 0.816863 0.219000 0.079 Uiso 1 1 calc R U . . .
C12 C 0.45044(14) 0.4540(3) 0.59389(16) 0.0686(8) Uani 1 1 d . . . . .
H12 H 0.492092 0.409211 0.598975 0.082 Uiso 1 1 calc R U . . .
C7 C 0.37117(13) 0.7418(2) 0.30954(13) 0.0524(6) Uani 1 1 d . . . . .
H7 H 0.414313 0.772779 0.324774 0.063 Uiso 1 1 calc R U . . .
C13 C 0.42049(17) 0.4998(4) 0.64868(15) 0.0784(10) Uani 1 1 d . . . . .
H13 H 0.442113 0.485725 0.690870 0.094 Uiso 1 1 calc R U . . .
C14 C 0.35906(17) 0.5659(4) 0.64173(14) 0.0724(9) Uani 1 1 d . . . . .
H14 H 0.338700 0.596641 0.678741 0.087 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 1.8933(13) 7_556 ?
Cu1 O1 1.8933(13) . ?
Cu1 N1 1.9941(16) 7_556 ?
Cu1 N1 1.9941(16) . ?
Cl1 C17 1.727(2) . ?
Cl2 C19 1.740(2) . ?
O1 C16 1.293(2) . ?
N1 C1 1.441(2) . ?
N1 C22 1.286(2) 7_556 ?
N2 C9 1.321(2) . ?
N2 C8 1.369(3) . ?
C1 C9 1.425(3) . ?
C1 C2 1.346(3) . ?
F1 C15 1.352(3) . ?
C9 C10 1.480(3) . ?
C3 C8 1.408(3) . ?
C3 C2 1.411(3) . ?
C3 C4 1.410(3) . ?
C16 C21 1.410(3) . ?
C16 C17 1.424(3) . ?
C20 H20 0.9300 . ?
C20 C19 1.361(3) . ?
C20 C21 1.409(3) . ?
C8 C7 1.415(3) . ?
C10 C15 1.383(3) . ?
C10 C11 1.388(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.385(4) . ?
C18 C17 1.373(3) . ?
C2 H2 0.9300 . ?
C21 C22 1.432(3) . ?
C22 H22 0.9300 . ?
C15 C14 1.364(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.361(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.392(4) . ?
C6 H6 0.9300 . ?
C6 C7 1.349(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C7 H7 0.9300 . ?
C13 H13 0.9300 . ?
C13 C14 1.372(4) . ?
C14 H14 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 7_556 . ?
O1 Cu1 N1 88.85(6) . . ?
O1 Cu1 N1 91.15(6) . 7_556 ?
O1 Cu1 N1 91.15(6) 7_556 . ?
O1 Cu1 N1 88.85(6) 7_556 7_556 ?
N1 Cu1 N1 180.0 . 7_556 ?
C16 O1 Cu1 129.78(13) . . ?
C1 N1 Cu1 120.24(12) . . ?
C22 N1 Cu1 124.44(14) 7_556 . ?
C22 N1 C1 115.15(16) 7_556 . ?
C9 N2 C8 118.23(18) . . ?
C9 C1 N1 119.07(18) . . ?
C2 C1 N1 121.24(18) . . ?
C2 C1 C9 119.70(18) . . ?
N2 C9 C1 122.06(19) . . ?
N2 C9 C10 116.25(18) . . ?
C1 C9 C10 121.68(17) . . ?
C8 C3 C2 116.95(19) . . ?
C8 C3 C4 119.5(2) . . ?
C4 C3 C2 123.6(2) . . ?
O1 C16 C21 124.25(18) . . ?
O1 C16 C17 120.05(19) . . ?
C21 C16 C17 115.68(18) . . ?
C19 C20 H20 119.9 . . ?
C19 C20 C21 120.1(2) . . ?
C21 C20 H20 119.9 . . ?
N2 C8 C3 122.96(18) . . ?
N2 C8 C7 118.5(2) . . ?
C3 C8 C7 118.6(2) . . ?
C15 C10 C9 122.6(2) . . ?
C15 C10 C11 116.6(2) . . ?
C11 C10 C9 120.7(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.5(2) . . ?
C20 C19 Cl2 119.9(2) . . ?
C20 C19 C18 120.8(2) . . ?
C18 C19 Cl2 119.24(17) . . ?
C1 C2 C3 120.08(19) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C16 C21 C22 121.82(18) . . ?
C20 C21 C16 121.18(19) . . ?
C20 C21 C22 116.95(19) . . ?
N1 C22 C21 126.92(19) 7_556 . ?
N1 C22 H22 116.5 7_556 . ?
C21 C22 H22 116.5 . . ?
F1 C15 C10 117.8(2) . . ?
F1 C15 C14 118.6(2) . . ?
C14 C15 C10 123.5(3) . . ?
C16 C17 Cl1 118.25(16) . . ?
C18 C17 Cl1 119.15(17) . . ?
C18 C17 C16 122.6(2) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.2(2) . . ?
C12 C11 H11 119.4 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.2 . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 H6 119.2 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C8 C7 H7 119.9 . . ?
C6 C7 C8 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.7(3) . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 118.5(3) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?

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 C16 C21 7.7(3) . . . . ?
Cu1 O1 C16 C17 -173.64(15) . . . . ?
Cu1 N1 C1 C9 -74.0(2) . . . . ?
Cu1 N1 C1 C2 106.28(19) . . . . ?
O1 C16 C21 C20 -179.5(2) . . . . ?
O1 C16 C21 C22 3.3(3) . . . . ?
O1 C16 C17 Cl1 -1.2(3) . . . . ?
O1 C16 C17 C18 178.1(2) . . . . ?
N1 Cu1 O1 C16 -13.09(18) 7_556 . . . ?
N1 Cu1 O1 C16 166.91(18) . . . . ?
N1 C1 C9 N2 179.91(17) . . . . ?
N1 C1 C9 C10 0.8(3) . . . . ?
N1 C1 C2 C3 -179.24(18) . . . . ?
N2 C9 C10 C15 118.1(2) . . . . ?
N2 C9 C10 C11 -58.9(3) . . . . ?
N2 C8 C7 C6 -180.0(2) . . . . ?
C1 C9 C10 C15 -62.7(3) . . . . ?
C1 C9 C10 C11 120.3(2) . . . . ?
F1 C15 C14 C13 -178.7(3) . . . . ?
C9 N2 C8 C3 1.8(3) . . . . ?
C9 N2 C8 C7 -178.1(2) . . . . ?
C9 C1 C2 C3 1.0(3) . . . . ?
C9 C10 C15 F1 1.7(3) . . . . ?
C9 C10 C15 C14 -177.3(2) . . . . ?
C9 C10 C11 C12 177.1(2) . . . . ?
C3 C8 C7 C6 0.1(4) . . . . ?
C3 C4 C5 C6 0.8(4) . . . . ?
C16 C21 C22 N1 -3.3(4) . . . 7_556 ?
C20 C21 C22 N1 179.3(2) . . . 7_556 ?
C8 N2 C9 C1 -1.0(3) . . . . ?
C8 N2 C9 C10 178.15(18) . . . . ?
C8 C3 C2 C1 -0.3(3) . . . . ?
C8 C3 C4 C5 -0.2(4) . . . . ?
C10 C15 C14 C13 0.3(5) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
C19 C20 C21 C16 0.1(4) . . . . ?
C19 C20 C21 C22 177.5(2) . . . . ?
C19 C18 C17 Cl1 -178.32(19) . . . . ?
C19 C18 C17 C16 2.4(4) . . . . ?
C2 C1 C9 N2 -0.4(3) . . . . ?
C2 C1 C9 C10 -179.49(19) . . . . ?
C2 C3 C8 N2 -1.1(3) . . . . ?
C2 C3 C8 C7 178.8(2) . . . . ?
C2 C3 C4 C5 -179.2(2) . . . . ?
C21 C16 C17 Cl1 177.54(16) . . . . ?
C21 C16 C17 C18 -3.1(3) . . . . ?
C21 C20 C19 Cl2 -179.62(18) . . . . ?
C21 C20 C19 C18 -1.0(4) . . . . ?
C22 N1 C1 C9 110.6(2) 7_556 . . . ?
C22 N1 C1 C2 -69.1(3) 7_556 . . . ?
C15 C10 C11 C12 -0.1(4) . . . . ?
C17 C16 C21 C20 1.9(3) . . . . ?
C17 C16 C21 C22 -175.4(2) . . . . ?
C17 C18 C19 Cl2 178.41(18) . . . . ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C11 C10 C15 F1 178.8(2) . . . . ?
C11 C10 C15 C14 -0.1(4) . . . . ?
C11 C12 C13 C14 0.0(5) . . . . ?
C4 C3 C8 N2 179.8(2) . . . . ?
C4 C3 C8 C7 -0.3(3) . . . . ?
C4 C3 C2 C1 178.7(2) . . . . ?
C4 C5 C6 C7 -1.0(5) . . . . ?
C5 C6 C7 C8 0.5(4) . . . . ?
C12 C13 C14 C15 -0.2(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.418
_oxdiff_exptl_absorpt_empirical_full_min 0.680
####################################################################### 
# 
# 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_20201110-czf-jcp-l25a
_database_code_depnum_ccdc_archive 'CCDC 2115674'
loop_
_audit_author_name
_audit_author_address
'Wen Ying Shen'
;Guangxi Normal University
China
;
_audit_update_record             
;
2023-01-07 deposited with the CCDC.	2023-01-10 downloaded from the CCDC.
;
_audit_creation_date             2023-01-07
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C44 H24 Cl4 Cu F2 N4 O2, 2(C H4 O)'
_chemical_formula_sum            'C46 H32 Cl4 Cu F2 N4 O4'
_chemical_formula_weight         948.09
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C184 H88 Cl16 Cu4 N32 O8 '
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   24.3709(2)
_cell_length_b                   11.58280(10)
_cell_length_c                   15.57890(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.6220(10)
_cell_angle_gamma                90
_cell_volume                     4291.38(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11714
_cell_measurement_temperature    295.29(10)
_cell_measurement_theta_max      77.2040
_cell_measurement_theta_min      2.9020
_shelx_estimated_absorpt_T_max   0.679
_shelx_estimated_absorpt_T_min   0.659
_exptl_absorpt_coefficient_mu    3.494
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic reddish red'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1932
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15217
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.282
_diffrn_reflns_theta_min         3.717
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.29(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     91.00 132.00   0.50    1.30    --  108.56  15.00  30.00   82
  2  ω    150.00 177.00   0.50    1.30    --  108.56  15.00  30.00   54
  3  ω     83.00 177.00   0.50    1.30    --  108.56   9.00 123.00  188
  4  ω     46.00  71.00   0.50    0.30    --   47.12   9.00 123.00   50
  5  ω    -25.00  27.00   0.50    0.30    --  -47.12   9.00 123.00  104
  6  ω    -48.00 -16.00   0.50    1.30    --  -88.50  45.00  60.00   64
  7  ω    -51.00 -18.00   0.50    1.30    --  -88.50  45.00  90.00   66
  8  ω    -50.00 -15.00   0.50    1.30    --  -88.50  61.00 -60.00   70
  9  ω     36.00  75.00   0.50    1.30    --  108.56 -94.00  30.00   78
 10  ω     46.00  95.00   0.50    0.30    --   47.12-125.00-120.00   98
 11  ω     75.00 111.00   0.50    1.30    --  108.56-125.00-150.00   72
 12  ω     36.00  65.00   0.50    1.30    --  108.56-125.00-150.00   58
 13  ω     49.00 101.00   0.50    1.30    --  108.56 -94.00-150.00  104
 14  ω     75.00 101.00   0.50    1.30    --  108.56 -94.00-120.00   52
 15  ω     41.00  67.00   0.50    1.30    --  108.56 -94.00-120.00   52
 16  ω     79.00 104.00   0.50    1.30    --  108.56 -94.00 120.00   50
 17  ω     38.00  64.00   0.50    1.30    --  108.56 -94.00 120.00   52
 18  ω     37.00  63.00   0.50    1.30    --  108.56 -61.00 120.00   52
 19  ω     43.00  71.00   0.50    1.30    --  108.56 -61.00 150.00   56
 20  ω     44.00  70.00   0.50    1.30    --  108.56 -61.00  90.00   52
 21  ω     73.00 105.00   0.50    1.30    --  108.56 -77.00-120.00   64
 22  ω     38.00  63.00   0.50    1.30    --  108.56 -77.00-120.00   50
 23  ω     36.00  61.00   0.50    1.30    --  108.56 -61.00-120.00   50
 24  ω     -6.00  20.00   0.50    0.30    --   47.12 -19.00-150.00   52
 25  ω    -23.00  27.00   0.50    0.30    --   47.12 -19.00-180.00  100
 26  ω     -3.00  24.00   0.50    0.30    --   47.12  -9.00 -51.00   54
 27  ω   -122.00 -24.00   0.50    0.30    --  -47.12  -9.00 -51.00  196
 28  ω   -148.00 -69.00   0.50    1.30    --  -88.50  -9.00 -51.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0315942000
_diffrn_orient_matrix_UB_12      -0.0118711000
_diffrn_orient_matrix_UB_13      -0.0966535000
_diffrn_orient_matrix_UB_21      -0.0562787000
_diffrn_orient_matrix_UB_22      -0.0051705000
_diffrn_orient_matrix_UB_23      0.0295005000
_diffrn_orient_matrix_UB_31      -0.0052324000
_diffrn_orient_matrix_UB_32      0.1324278000
_diffrn_orient_matrix_UB_33      -0.0074961000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4073
_reflns_number_total             4347
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2013/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.423
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4347
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0533P)²+2.8959P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(F1')
3. Others
 Sof(H18)=Sof(F1')=1-FVAR(1)
 Sof(F1)=Sof(H22)=FVAR(1)
4.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C9(H9), C5(H5), C2(H2), C11(H11), C18(H18), C22(H22), C12(H12),
 C14(H14), C13(H13), C21(H21), C19(H19), C20(H20)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
4.c Idealised tetrahedral OH refined as rotating group:
 O2(H2A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.5000 0.19691(2) 0.2500 0.03832(11) Uani 1 2 d S T P . .
Cl02 Cl 0.27302(2) -0.13234(5) 0.28399(5) 0.07814(19) Uani 1 1 d . . . . .
Cl03 Cl 0.23643(3) 0.08822(6) 0.37826(6) 0.0890(2) Uani 1 1 d . . . . .
O1 O 0.44601(5) 0.07943(9) 0.25288(9) 0.0483(3) Uani 1 1 d . . . . .
N1 N 0.46368(5) 0.30716(11) 0.31839(9) 0.0383(3) Uani 1 1 d . . . . .
N2 N 0.57520(6) 0.51552(12) 0.40977(10) 0.0479(3) Uani 1 1 d . . . . .
F1 F 0.64828(6) 0.37930(13) 0.33435(12) 0.0662(4) Uani 0.790(2) 1 d . . P A 1
C8 C 0.48979(7) 0.41535(13) 0.34562(11) 0.0386(3) Uani 1 1 d . . . . .
C16 C 0.54802(7) 0.41764(13) 0.38705(11) 0.0407(3) Uani 1 1 d . . . . .
C7 C 0.41629(7) 0.28705(14) 0.34104(11) 0.0412(3) Uani 1 1 d . . . . .
H7 H 0.4027 0.3450 0.3720 0.049 Uiso 1 1 calc R U . . .
C6 C 0.38315(7) 0.18482(14) 0.32302(11) 0.0419(3) Uani 1 1 d . . . . .
C1 C 0.39972(7) 0.08644(13) 0.28054(11) 0.0407(3) Uani 1 1 d . . . . .
O2 O 0.66022(9) 0.53492(18) 0.56663(14) 0.0979(7) Uani 1 1 d . . . . .
H2A H 0.6400 0.5194 0.5187 0.147 Uiso 1 1 calc R U . . .
C10 C 0.48917(8) 0.62284(14) 0.35307(11) 0.0450(4) Uani 1 1 d . . . . .
C9 C 0.46096(7) 0.51753(14) 0.33043(12) 0.0441(4) Uani 1 1 d . . . . .
H9 H 0.4227 0.5173 0.3051 0.053 Uiso 1 1 calc R U . . .
C17 C 0.58201(7) 0.31081(14) 0.40913(11) 0.0425(4) Uani 1 1 d . . . . .
C15 C 0.54734(8) 0.61776(14) 0.39238(12) 0.0477(4) Uani 1 1 d . . . . .
C5 C 0.33227(8) 0.18267(16) 0.35213(13) 0.0499(4) Uani 1 1 d . . . . .
H5 H 0.3217 0.2474 0.3799 0.060 Uiso 1 1 calc R U . . .
C2 C 0.36335(8) -0.01033(15) 0.26946(13) 0.0486(4) Uani 1 1 d . . . . .
H2 H 0.3729 -0.0759 0.2415 0.058 Uiso 1 1 calc R U . . .
C11 C 0.46318(9) 0.73244(16) 0.33499(13) 0.0544(4) Uani 1 1 d . . . . .
H11 H 0.4249 0.7372 0.3104 0.065 Uiso 1 1 calc R U . . .
C18 C 0.63352(8) 0.29949(16) 0.38610(13) 0.0530(4) Uani 1 1 d . . . . .
H18 H 0.6450 0.3572 0.3524 0.064 Uiso 0.210(2) 1 calc R U P A 2
C3 C 0.31454(8) -0.00959(16) 0.29888(13) 0.0516(4) Uani 1 1 d . . . . .
C4 C 0.29818(8) 0.08781(18) 0.34045(14) 0.0547(4) Uani 1 1 d . . . . .
C22 C 0.56599(9) 0.22198(16) 0.45862(12) 0.0523(4) Uani 1 1 d . . . . .
H22 H 0.5313 0.2255 0.4741 0.063 Uiso 0.790(2) 1 calc R U P A 1
C12 C 0.49414(11) 0.83060(16) 0.35344(15) 0.0630(5) Uani 1 1 d . . . . .
H12 H 0.4770 0.9020 0.3398 0.076 Uiso 1 1 calc R U . . .
C14 C 0.57798(10) 0.72183(17) 0.41252(15) 0.0609(5) Uani 1 1 d . . . . .
H14 H 0.6160 0.7196 0.4391 0.073 Uiso 1 1 calc R U . . .
C13 C 0.55156(11) 0.82511(17) 0.39282(16) 0.0660(6) Uani 1 1 d . . . . .
H13 H 0.5720 0.8931 0.4057 0.079 Uiso 1 1 calc R U . . .
C21 C 0.60088(11) 0.12868(18) 0.48513(14) 0.0664(6) Uani 1 1 d . . . . .
H21 H 0.5898 0.0708 0.5191 0.080 Uiso 1 1 calc R U . . .
C19 C 0.66840(10) 0.2065(2) 0.41104(17) 0.0673(6) Uani 1 1 d . . . . .
H19 H 0.7027 0.2013 0.3942 0.081 Uiso 1 1 calc R U . . .
C20 C 0.65172(12) 0.1211(2) 0.46148(16) 0.0747(7) Uani 1 1 d . . . . .
H20 H 0.6750 0.0581 0.4795 0.090 Uiso 1 1 calc R U . . .
C23 C 0.69125(17) 0.4406(3) 0.5986(3) 0.1309(16) Uani 1 1 d . . . . .
H23A H 0.6679 0.3730 0.5884 0.196 Uiso 1 1 calc R U . . .
H23B H 0.7059 0.4499 0.6606 0.196 Uiso 1 1 calc R U . . .
H23C H 0.7218 0.4324 0.5693 0.196 Uiso 1 1 calc R U . . .
F1' F 0.5198(2) 0.2243(5) 0.4746(4) 0.0662(4) Uani 0.210(2) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9002(11) . ?
Cu1 O1 1.9003(11) 2_655 ?
Cu1 N1 1.9904(13) 2_655 ?
Cu1 N1 1.9903(13) . ?
Cl02 C3 1.7311(18) . ?
Cl03 C4 1.7318(19) . ?
O1 C1 1.295(2) . ?
N1 C8 1.4273(19) . ?
N1 C7 1.300(2) . ?
N2 C16 1.322(2) . ?
N2 C15 1.363(2) . ?
F1 C18 1.327(3) . ?
C8 C16 1.425(2) . ?
C8 C9 1.370(2) . ?
C16 C17 1.487(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.426(2) . ?
C6 C1 1.420(2) . ?
C6 C5 1.410(2) . ?
C1 C2 1.416(2) . ?
O2 H2A 0.8200 . ?
O2 C23 1.360(4) . ?
C10 C9 1.407(2) . ?
C10 C15 1.417(3) . ?
C10 C11 1.419(2) . ?
C9 H9 0.9300 . ?
C17 C18 1.385(3) . ?
C17 C22 1.392(3) . ?
C15 C14 1.417(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.365(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.365(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.360(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(3) . ?
C3 C4 1.401(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.381(3) . ?
C22 F1' 1.206(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.401(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.361(3) . ?
C13 H13 0.9300 . ?
C21 H21 0.9300 . ?
C21 C20 1.370(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(4) . ?
C20 H20 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 88.53(7) . 2_655 ?
O1 Cu1 N1 149.69(6) 2_655 . ?
O1 Cu1 N1 149.69(6) . 2_655 ?
O1 Cu1 N1 93.19(5) . . ?
O1 Cu1 N1 93.18(5) 2_655 2_655 ?
N1 Cu1 N1 100.18(8) . 2_655 ?
C1 O1 Cu1 128.39(10) . . ?
C8 N1 Cu1 120.06(10) . . ?
C7 N1 Cu1 123.75(11) . . ?
C7 N1 C8 116.18(13) . . ?
C16 N2 C15 119.57(15) . . ?
C16 C8 N1 119.08(13) . . ?
C9 C8 N1 121.91(14) . . ?
C9 C8 C16 118.97(14) . . ?
N2 C16 C8 121.90(14) . . ?
N2 C16 C17 115.50(14) . . ?
C8 C16 C17 122.59(14) . . ?
N1 C7 H7 116.8 . . ?
N1 C7 C6 126.42(15) . . ?
C6 C7 H7 116.8 . . ?
C1 C6 C7 123.47(15) . . ?
C5 C6 C7 116.82(15) . . ?
C5 C6 C1 119.69(15) . . ?
O1 C1 C6 124.23(14) . . ?
O1 C1 C2 118.52(15) . . ?
C2 C1 C6 117.24(16) . . ?
C23 O2 H2A 109.5 . . ?
C9 C10 C15 117.40(15) . . ?
C9 C10 C11 123.60(17) . . ?
C15 C10 C11 118.94(16) . . ?
C8 C9 C10 120.11(16) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C18 C17 C16 120.63(16) . . ?
C18 C17 C22 116.95(16) . . ?
C22 C17 C16 122.26(16) . . ?
N2 C15 C10 122.01(15) . . ?
N2 C15 C14 118.67(18) . . ?
C14 C15 C10 119.31(16) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 C6 121.56(18) . . ?
C4 C5 H5 119.2 . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.49(17) . . ?
C3 C2 H2 119.3 . . ?
C10 C11 H11 119.9 . . ?
C12 C11 C10 120.2(2) . . ?
C12 C11 H11 119.9 . . ?
F1 C18 C17 118.21(17) . . ?
F1 C18 C19 119.0(2) . . ?
C17 C18 H18 118.6 . . ?
C19 C18 C17 122.7(2) . . ?
C19 C18 H18 118.6 . . ?
C2 C3 Cl02 118.46(15) . . ?
C2 C3 C4 121.13(16) . . ?
C4 C3 Cl02 120.40(15) . . ?
C5 C4 Cl03 120.07(16) . . ?
C5 C4 C3 118.89(17) . . ?
C3 C4 Cl03 121.03(14) . . ?
C17 C22 H22 119.5 . . ?
C21 C22 C17 121.0(2) . . ?
C21 C22 H22 119.5 . . ?
F1' C22 C17 119.1(3) . . ?
F1' C22 C21 119.8(3) . . ?
C11 C12 H12 119.7 . . ?
C11 C12 C13 120.62(18) . . ?
C13 C12 H12 119.7 . . ?
C15 C14 H14 120.1 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H14 120.1 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.09(19) . . ?
C14 C13 H13 119.5 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C18 C19 H19 120.6 . . ?
C18 C19 C20 118.8(2) . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 120.24(19) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
O2 C23 H23A 109.5 . . ?
O2 C23 H23B 109.5 . . ?
O2 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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 -6.4(2) . . . . ?
Cu1 O1 C1 C2 174.69(12) . . . . ?
Cu1 N1 C8 C16 -48.17(19) . . . . ?
Cu1 N1 C8 C9 129.58(14) . . . . ?
Cu1 N1 C7 C6 1.2(2) . . . . ?
Cl02 C3 C4 Cl03 0.2(3) . . . . ?
Cl02 C3 C4 C5 179.17(15) . . . . ?
O1 C1 C2 C3 178.52(17) . . . . ?
N1 C8 C16 N2 176.58(15) . . . . ?
N1 C8 C16 C17 -4.6(2) . . . . ?
N1 C8 C9 C10 -175.76(15) . . . . ?
N1 C7 C6 C1 3.4(3) . . . . ?
N1 C7 C6 C5 -178.54(17) . . . . ?
N2 C16 C17 C18 -50.1(2) . . . . ?
N2 C16 C17 C22 125.28(19) . . . . ?
N2 C15 C14 C13 177.6(2) . . . . ?
F1 C18 C19 C20 -177.1(2) . . . . ?
C8 N1 C7 C6 -178.70(15) . . . . ?
C8 C16 C17 C18 131.01(18) . . . . ?
C8 C16 C17 C22 -53.6(2) . . . . ?
C16 N2 C15 C10 2.2(3) . . . . ?
C16 N2 C15 C14 -176.32(18) . . . . ?
C16 C8 C9 C10 2.0(2) . . . . ?
C16 C17 C18 F1 -8.5(3) . . . . ?
C16 C17 C18 C19 174.76(18) . . . . ?
C16 C17 C22 C21 -173.88(17) . . . . ?
C16 C17 C22 F1' 9.8(5) . . . . ?
C7 N1 C8 C16 131.70(16) . . . . ?
C7 N1 C8 C9 -50.6(2) . . . . ?
C7 C6 C1 O1 -0.8(3) . . . . ?
C7 C6 C1 C2 178.06(16) . . . . ?
C7 C6 C5 C4 -178.14(17) . . . . ?
C6 C1 C2 C3 -0.4(3) . . . . ?
C6 C5 C4 Cl03 179.30(15) . . . . ?
C6 C5 C4 C3 0.3(3) . . . . ?
C1 C6 C5 C4 0.0(3) . . . . ?
C1 C2 C3 Cl02 -179.10(14) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C10 C15 C14 C13 -1.0(3) . . . . ?
C10 C11 C12 C13 -1.9(3) . . . . ?
C9 C8 C16 N2 -1.2(3) . . . . ?
C9 C8 C16 C17 177.60(16) . . . . ?
C9 C10 C15 N2 -1.4(3) . . . . ?
C9 C10 C15 C14 177.10(17) . . . . ?
C9 C10 C11 C12 -175.49(19) . . . . ?
C17 C18 C19 C20 -0.4(3) . . . . ?
C17 C22 C21 C20 -1.3(3) . . . . ?
C15 N2 C16 C8 -0.9(3) . . . . ?
C15 N2 C16 C17 -179.77(16) . . . . ?
C15 C10 C9 C8 -0.7(2) . . . . ?
C15 C10 C11 C12 1.5(3) . . . . ?
C15 C14 C13 C12 0.6(3) . . . . ?
C5 C6 C1 O1 -178.80(16) . . . . ?
C5 C6 C1 C2 0.1(2) . . . . ?
C2 C3 C4 Cl03 -179.63(15) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C11 C10 C9 C8 176.27(17) . . . . ?
C11 C10 C15 N2 -178.54(17) . . . . ?
C11 C10 C15 C14 0.0(3) . . . . ?
C11 C12 C13 C14 0.9(4) . . . . ?
C18 C17 C22 C21 1.6(3) . . . . ?
C18 C17 C22 F1' -174.6(4) . . . . ?
C18 C19 C20 C21 0.8(4) . . . . ?
C22 C17 C18 F1 175.87(17) . . . . ?
C22 C17 C18 C19 -0.8(3) . . . . ?
C22 C21 C20 C19 0.0(4) . . . . ?
F1' C22 C21 C20 175.0(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.810
_oxdiff_exptl_absorpt_empirical_full_min 0.644
