# 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_Compound_III
_database_code_depnum_ccdc_archive 'CCDC 2158096'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2022-12-24 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-23
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C24 H20 Cu F N8 O2), 2(N O3), 5(H2 O)'
_chemical_formula_sum            'C48 H50 Cu2 F2 N18 O15'
_chemical_formula_weight         1284.14
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 2/c'
_space_group_name_Hall           '-P 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'

_cell_length_a                   15.6860(11)
_cell_length_b                   9.7121(9)
_cell_length_c                   18.3253(18)
_cell_angle_alpha                90
_cell_angle_beta                 104.091(9)
_cell_angle_gamma                90
_cell_volume                     2707.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1724
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.8770
_cell_measurement_theta_min      3.7810
_shelx_estimated_absorpt_T_max   0.910
_shelx_estimated_absorpt_T_min   0.670
_exptl_absorpt_coefficient_mu    0.878
_exptl_absorpt_correction_T_max  0.930
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1320
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-20 -5 -1 0.2165
19 0 7 0.2560
-9 8 20 0.0967
-5 -13 9 0.0506
2 -14 -2 0.0390
19 -7 -12 0.0832
4 -11 -14 0.0696
10 1 -25 0.1029
19 3 -16 0.0859
7 12 -11 0.0484
-2 13 5 0.0772
-3 -5 24 0.1525
-17 -6 -8 0.1871
-11 11 10 0.1216

_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_av_unetI/netI     0.2357
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            8982
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.039
_diffrn_reflns_theta_max         25.039
_diffrn_reflns_theta_min         3.107
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  39.00   1.00    5.00    --   14.20  77.00  60.00   37
  2  ω    -37.00  37.00   1.00    5.00    --   14.20 -77.00-150.00   74
  3  ω    -46.00  29.00   1.00    5.00    --   14.20 -19.00  60.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1736
_reflns_number_total             4614
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.402
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.706
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     403
_refine_ls_number_reflns         4614
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0466
_refine_ls_restrained_S_all      0.709
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0146P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O5-N9 \\sim O4-N9 \\sim O3B-N9 \\sim O3A-N9
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C4, O2
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C1, O1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, C4
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 N2, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 C22, C23
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(O3A)=1-FVAR(1)
 Sof(O3B)=FVAR(1)
 Fixed Sof: H1WA(0.5) H1WB(0.5)
5.a Free rotating group:
 O1W(H1WA,H1WB), O3W(H3WA,H3WB), O2W(H2WA,H2WB)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H2), N4(H4), N7(H7), C3(H3), C5(H5), C6(H6), C7(H7A), C8(H8), C11(H11),
 C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C21(H21),
  C22(H22), C23(H23), C24(H24)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.73685(3) 0.50585(7) 0.41983(3) 0.03365(16) Uani 1 1 d . . . . .
F1 F 0.66987(15) 0.3673(3) 0.12959(15) 0.0610(9) Uani 1 1 d . . . . .
O1 O 0.63764(14) 0.5060(4) 0.24810(14) 0.0451(8) Uani 1 1 d . . . . .
O2 O 0.89730(16) 0.3604(3) 0.39750(18) 0.0490(10) Uani 1 1 d . . . . .
N2 N 0.76869(19) 0.4387(3) 0.3240(2) 0.0301(10) Uani 1 1 d . . . . .
N1 N 0.8632(2) 0.3005(4) 0.2741(2) 0.0458(12) Uani 1 1 d . . . . .
H2 H 0.912513 0.258185 0.279469 0.055 Uiso 1 1 calc R U . . .
N3 N 0.8179(2) 0.6657(4) 0.4238(2) 0.0320(10) Uani 1 1 d . . . . .
N4 N 0.9253(2) 0.5967(4) 0.5312(2) 0.0383(11) Uani 1 1 d . . . . .
H4 H 0.980602 0.603524 0.551787 0.046 Uiso 1 1 calc R U . . .
N5 N 0.8001(2) 0.4653(4) 0.53340(19) 0.0332(11) Uani 1 1 d . . . . .
N6 N 0.6305(2) 0.6219(4) 0.4363(2) 0.0294(10) Uani 1 1 d . . . . .
N7 N 0.5267(2) 0.4664(4) 0.3682(2) 0.0375(11) Uani 1 1 d . . . . .
H7 H 0.477649 0.467356 0.334666 0.045 Uiso 1 1 calc R U . . .
N8 N 0.6578(2) 0.3395(4) 0.4073(2) 0.0313(10) Uani 1 1 d . . . . .
C1 C 0.7079(3) 0.4415(4) 0.2566(3) 0.0302(12) Uani 1 1 d . . . . .
C2 C 0.7293(3) 0.3672(5) 0.1965(3) 0.0380(14) Uani 1 1 d . . . . .
C3 C 0.8056(3) 0.3000(5) 0.2055(3) 0.0481(15) Uani 1 1 d . . . . .
H3 H 0.819061 0.253593 0.165367 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8460(3) 0.3649(5) 0.3345(3) 0.0361(13) Uani 1 1 d . . . . .
C5 C 0.6433(3) 0.7403(5) 0.4757(3) 0.0380(14) Uani 1 1 d . . . . .
H5 H 0.701171 0.766465 0.496515 0.046 Uiso 1 1 calc R U . . .
C6 C 0.5786(3) 0.8256(5) 0.4879(3) 0.0463(14) Uani 1 1 d . . . . .
H6 H 0.591512 0.904539 0.517213 0.056 Uiso 1 1 calc R U . . .
C7 C 0.4931(3) 0.7879(6) 0.4542(3) 0.0548(16) Uani 1 1 d . . . . .
H7A H 0.446464 0.843378 0.459004 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4777(3) 0.6701(5) 0.4142(3) 0.0492(15) Uani 1 1 d . . . . .
H8 H 0.420262 0.644129 0.391747 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5466(3) 0.5876(5) 0.4064(3) 0.0313(13) Uani 1 1 d . . . . .
C10 C 0.5707(3) 0.3440(5) 0.3738(3) 0.0319(13) Uani 1 1 d . . . . .
C11 C 0.5272(3) 0.2218(6) 0.3475(3) 0.0470(15) Uani 1 1 d . . . . .
H11 H 0.467361 0.224762 0.324756 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5690(3) 0.1001(5) 0.3540(3) 0.0551(16) Uani 1 1 d . . . . .
H12 H 0.538904 0.020469 0.334661 0.066 Uiso 1 1 calc R U . . .
C13 C 0.6580(3) 0.0948(5) 0.3902(3) 0.0508(15) Uani 1 1 d . . . . .
H13 H 0.688603 0.011992 0.396554 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6985(3) 0.2160(5) 0.4159(3) 0.0410(14) Uani 1 1 d . . . . .
H14 H 0.757659 0.213228 0.440770 0.049 Uiso 1 1 calc R U . . .
C15 C 0.7616(3) 0.3801(5) 0.5745(3) 0.0419(13) Uani 1 1 d . . . . .
H15 H 0.703897 0.353407 0.553453 0.050 Uiso 1 1 calc R U . . .
C16 C 0.7999(3) 0.3310(5) 0.6434(3) 0.0471(14) Uani 1 1 d . . . . .
H16 H 0.769611 0.273875 0.669081 0.057 Uiso 1 1 calc R U . . .
C17 C 0.8863(3) 0.3686(5) 0.6745(3) 0.0538(16) Uani 1 1 d . . . . .
H17 H 0.915810 0.334627 0.721235 0.065 Uiso 1 1 calc R U . . .
C18 C 0.9274(3) 0.4548(5) 0.6366(3) 0.0482(16) Uani 1 1 d . . . . .
H18 H 0.985245 0.481015 0.657243 0.058 Uiso 1 1 calc R U . . .
C19 C 0.8827(2) 0.5044(6) 0.5663(2) 0.0321(11) Uani 1 1 d . . . . .
C20 C 0.8977(3) 0.6806(5) 0.4697(3) 0.0338(13) Uani 1 1 d . . . . .
C21 C 0.9555(3) 0.7844(5) 0.4573(3) 0.0510(16) Uani 1 1 d . . . . .
H21 H 1.010410 0.795211 0.490348 0.061 Uiso 1 1 calc R U . . .
C22 C 0.9305(3) 0.8669(6) 0.3977(3) 0.0623(17) Uani 1 1 d . . . . .
H22 H 0.969575 0.932751 0.388304 0.075 Uiso 1 1 calc R U . . .
C23 C 0.8477(3) 0.8566(5) 0.3494(3) 0.0594(16) Uani 1 1 d . . . . .
H23 H 0.829337 0.916448 0.308976 0.071 Uiso 1 1 calc R U . . .
C24 C 0.7949(3) 0.7551(5) 0.3638(3) 0.0472(15) Uani 1 1 d . . . . .
H24 H 0.739668 0.745075 0.331161 0.057 Uiso 1 1 calc R U . . .
O1W O 1.000000 0.1250(5) 0.250000 0.0721(17) Uani 1 2 d GS T P . .
H1WA H 0.965117 0.089695 0.211691 0.108 Uiso 0.5 1 d G U P . .
H1WB H 1.028682 0.057007 0.272863 0.108 Uiso 0.5 1 d G U P . .
O3A O 0.8527(7) -0.025(2) 0.0444(7) 0.188(10) Uani 0.512(17) 1 d D . P A 2
O3B O 0.8763(12) 0.0953(13) 0.0878(10) 0.170(9) Uani 0.488(17) 1 d D . P A 1
O4 O 0.8541(3) -0.0152(5) 0.1707(3) 0.138(2) Uani 1 1 d D . . . .
O5 O 0.7410(4) -0.0164(8) 0.0834(3) 0.188(3) Uani 1 1 d D . . . .
N9 N 0.8218(5) 0.0101(11) 0.1014(5) 0.125(3) Uani 1 1 d D . . . .
O3W O 0.5834(4) 0.7876(7) 0.2639(4) 0.175(2) Uani 1 1 d G . . . .
H3WA H 0.617043 0.826247 0.240108 0.262 Uiso 1 1 d G U . . .
H3WB H 0.600371 0.704214 0.268349 0.262 Uiso 1 1 d G U . . .
O2W O 0.6573(3) -0.0086(11) 0.1975(3) 0.204(2) Uani 1 1 d G . . . .
H2WA H 0.620153 -0.015187 0.155328 0.306 Uiso 1 1 d G U . . .
H2WB H 0.706972 -0.009042 0.186614 0.306 Uiso 1 1 d G 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 N2 2.045(3) . ?
Cu1 N3 1.997(3) . ?
Cu1 N5 2.113(3) . ?
Cu1 N6 2.094(3) . ?
Cu1 N8 2.016(3) . ?
F1 C2 1.348(4) . ?
O1 C1 1.244(4) . ?
O2 C4 1.237(5) . ?
N2 C1 1.365(5) . ?
N2 C4 1.381(5) . ?
N1 H2 0.8600 . ?
N1 C3 1.357(5) . ?
N1 C4 1.355(5) . ?
N3 C20 1.335(5) . ?
N3 C24 1.379(5) . ?
N4 H4 0.8600 . ?
N4 C19 1.369(5) . ?
N4 C20 1.372(5) . ?
N5 C15 1.356(5) . ?
N5 C19 1.345(4) . ?
N6 C5 1.347(5) . ?
N6 C9 1.339(5) . ?
N7 H7 0.8600 . ?
N7 C9 1.366(5) . ?
N7 C10 1.366(5) . ?
N8 C10 1.356(5) . ?
N8 C14 1.350(5) . ?
C1 C2 1.424(5) . ?
C2 C3 1.338(5) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.369(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.383(5) . ?
C7 H7A 0.9300 . ?
C7 C8 1.348(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(5) . ?
C10 C11 1.395(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.343(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.393(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C15 C16 1.346(6) . ?
C16 H16 0.9300 . ?
C16 C17 1.385(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.347(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.393(5) . ?
C20 C21 1.411(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.335(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.386(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.355(5) . ?
C24 H24 0.9300 . ?
O1W H1WA 0.85(7) 2_755 ?
O1W H1WA 0.8502 . ?
O1W H1WB 0.8499 . ?
O1W H1WB 0.85(11) 2_755 ?
O3A N9 1.301(12) . ?
O3B N9 1.258(11) . ?
O4 N9 1.271(7) . ?
O5 N9 1.256(7) . ?
O3W H3WA 0.8499 . ?
O3W H3WB 0.8500 . ?
O2W H2WA 0.8495 . ?
O2W H2WB 0.8503 . ?

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
N2 Cu1 N5 129.19(13) . . ?
N2 Cu1 N6 131.63(14) . . ?
N3 Cu1 N2 89.59(13) . . ?
N3 Cu1 N5 88.10(15) . . ?
N3 Cu1 N6 95.65(14) . . ?
N3 Cu1 N8 174.92(16) . . ?
N6 Cu1 N5 99.08(13) . . ?
N8 Cu1 N2 85.33(13) . . ?
N8 Cu1 N5 95.23(15) . . ?
N8 Cu1 N6 87.62(15) . . ?
C1 N2 Cu1 120.5(3) . . ?
C1 N2 C4 122.1(4) . . ?
C4 N2 Cu1 115.8(3) . . ?
C3 N1 H2 118.7 . . ?
C4 N1 H2 118.7 . . ?
C4 N1 C3 122.5(4) . . ?
C20 N3 Cu1 126.7(3) . . ?
C20 N3 C24 117.2(4) . . ?
C24 N3 Cu1 114.8(3) . . ?
C19 N4 H4 113.5 . . ?
C19 N4 C20 133.0(4) . . ?
C20 N4 H4 113.5 . . ?
C15 N5 Cu1 119.7(3) . . ?
C19 N5 Cu1 124.0(3) . . ?
C19 N5 C15 115.7(4) . . ?
C5 N6 Cu1 121.1(3) . . ?
C9 N6 Cu1 123.0(3) . . ?
C9 N6 C5 115.8(4) . . ?
C9 N7 H7 114.2 . . ?
C10 N7 H7 114.2 . . ?
C10 N7 C9 131.5(4) . . ?
C10 N8 Cu1 123.4(3) . . ?
C14 N8 Cu1 116.0(3) . . ?
C14 N8 C10 118.5(4) . . ?
O1 C1 N2 121.7(4) . . ?
O1 C1 C2 121.8(4) . . ?
N2 C1 C2 116.5(4) . . ?
F1 C2 C1 117.5(4) . . ?
C3 C2 F1 120.8(5) . . ?
C3 C2 C1 121.6(5) . . ?
N1 C3 H3 120.5 . . ?
C2 C3 N1 119.1(4) . . ?
C2 C3 H3 120.5 . . ?
O2 C4 N2 119.9(5) . . ?
O2 C4 N1 122.1(4) . . ?
N1 C4 N2 118.0(4) . . ?
N6 C5 H5 117.1 . . ?
N6 C5 C6 125.7(4) . . ?
C6 C5 H5 117.1 . . ?
C5 C6 H6 121.8 . . ?
C5 C6 C7 116.3(4) . . ?
C7 C6 H6 121.8 . . ?
C6 C7 H7A 120.2 . . ?
C8 C7 C6 119.5(5) . . ?
C8 C7 H7A 120.2 . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.5(5) . . ?
C9 C8 H8 119.7 . . ?
N6 C9 N7 120.2(4) . . ?
N6 C9 C8 122.0(4) . . ?
N7 C9 C8 117.7(4) . . ?
N7 C10 C11 121.3(4) . . ?
N8 C10 N7 119.8(4) . . ?
N8 C10 C11 118.9(4) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 C10 122.1(4) . . ?
C12 C11 H11 119.0 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 121.3 . . ?
C14 C13 C12 117.4(4) . . ?
C14 C13 H13 121.3 . . ?
N8 C14 C13 124.0(4) . . ?
N8 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N5 C15 H15 117.3 . . ?
C16 C15 N5 125.4(5) . . ?
C16 C15 H15 117.3 . . ?
C15 C16 H16 121.3 . . ?
C15 C16 C17 117.5(5) . . ?
C17 C16 H16 121.3 . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.7(4) . . ?
C19 C18 H18 120.2 . . ?
N4 C19 C18 117.9(4) . . ?
N5 C19 N4 120.1(4) . . ?
N5 C19 C18 122.0(4) . . ?
N3 C20 N4 120.9(4) . . ?
N3 C20 C21 121.1(5) . . ?
N4 C20 C21 118.0(4) . . ?
C20 C21 H21 120.4 . . ?
C22 C21 C20 119.2(5) . . ?
C22 C21 H21 120.4 . . ?
C21 C22 H22 119.3 . . ?
C21 C22 C23 121.5(5) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 121.6 . . ?
C24 C23 C22 116.8(5) . . ?
C24 C23 H23 121.6 . . ?
N3 C24 H24 118.0 . . ?
C23 C24 N3 124.1(4) . . ?
C23 C24 H24 118.0 . . ?
H1WA O1W H1WA 132.4 . 2_755 ?
H1WA O1W H1WB 28.7 . 2_755 ?
H1WA O1W H1WB 104.5 . . ?
H1WA O1W H1WB 104.5 2_755 2_755 ?
H1WB O1W H1WA 28.7 . 2_755 ?
H1WB O1W H1WB 78.0 . 2_755 ?
O3B N9 O4 101.6(11) . . ?
O4 N9 O3A 128.0(10) . . ?
O5 N9 O3A 106.5(10) . . ?
O5 N9 O3B 140.6(13) . . ?
O5 N9 O4 110.8(8) . . ?
H3WA O3W H3WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H2 O1W 0.86 2.05 2.858(5) 155.8 . yes
N4 H4 O2 0.86 1.95 2.802(4) 173.4 3_766 yes
N7 H7 O1 0.86 2.09 2.943(4) 170.1 2_655 yes
C3 H3 O4 0.93 2.66 3.255(7) 122.0 . yes
O1W H1WA O3B 0.85 2.36 3.14(2) 153.7 . yes
O1W H1WA O4 0.85 2.00 2.753(5) 147.4 . yes
O3W H3WA O2W 0.85 1.95 2.726(12) 150.3 1_565 yes
O3W H3WB O1 0.85 2.07 2.899(6) 164.5 . yes
O2W H2WB O4 0.85 2.40 3.243(7) 173.5 . yes
O2W H2WB O5 0.85 2.09 2.727(8) 131.6 . yes

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 N2 C1 O1 12.9(5) . . . . ?
Cu1 N2 C1 C2 -167.2(3) . . . . ?
Cu1 N2 C4 O2 -10.6(5) . . . . ?
Cu1 N2 C4 N1 170.1(3) . . . . ?
Cu1 N3 C20 N4 -14.0(6) . . . . ?
Cu1 N3 C20 C21 167.2(3) . . . . ?
Cu1 N3 C24 C23 -168.9(4) . . . . ?
Cu1 N5 C15 C16 170.2(4) . . . . ?
Cu1 N5 C19 N4 12.5(6) . . . . ?
Cu1 N5 C19 C18 -168.1(3) . . . . ?
Cu1 N6 C5 C6 178.0(3) . . . . ?
Cu1 N6 C9 N7 5.6(6) . . . . ?
Cu1 N6 C9 C8 -176.0(3) . . . . ?
Cu1 N8 C10 N7 -20.7(6) . . . . ?
Cu1 N8 C10 C11 160.9(3) . . . . ?
Cu1 N8 C14 C13 -161.5(4) . . . . ?
F1 C2 C3 N1 -178.9(4) . . . . ?
O1 C1 C2 F1 -0.9(6) . . . . ?
O1 C1 C2 C3 178.8(4) . . . . ?
N2 C1 C2 F1 179.3(3) . . . . ?
N2 C1 C2 C3 -1.0(6) . . . . ?
N3 C20 C21 C22 -1.6(7) . . . . ?
N4 C20 C21 C22 179.6(5) . . . . ?
N5 C15 C16 C17 -1.0(7) . . . . ?
N6 C5 C6 C7 -2.4(7) . . . . ?
N7 C10 C11 C12 -178.6(5) . . . . ?
N8 C10 C11 C12 -0.3(8) . . . . ?
C1 N2 C4 O2 -176.8(4) . . . . ?
C1 N2 C4 N1 3.9(6) . . . . ?
C1 C2 C3 N1 1.4(7) . . . . ?
C3 N1 C4 O2 177.2(4) . . . . ?
C3 N1 C4 N2 -3.5(7) . . . . ?
C4 N2 C1 O1 178.5(4) . . . . ?
C4 N2 C1 C2 -1.7(6) . . . . ?
C4 N1 C3 C2 1.0(7) . . . . ?
C5 N6 C9 N7 -177.1(4) . . . . ?
C5 N6 C9 C8 1.3(7) . . . . ?
C5 C6 C7 C8 2.2(7) . . . . ?
C6 C7 C8 C9 -0.4(8) . . . . ?
C7 C8 C9 N6 -1.4(8) . . . . ?
C7 C8 C9 N7 177.0(5) . . . . ?
C9 N6 C5 C6 0.7(7) . . . . ?
C9 N7 C10 N8 -19.2(7) . . . . ?
C9 N7 C10 C11 159.1(5) . . . . ?
C10 N7 C9 N6 26.9(7) . . . . ?
C10 N7 C9 C8 -151.5(5) . . . . ?
C10 N8 C14 C13 2.7(7) . . . . ?
C10 C11 C12 C13 2.0(8) . . . . ?
C11 C12 C13 C14 -1.3(8) . . . . ?
C12 C13 C14 N8 -1.0(8) . . . . ?
C14 N8 C10 N7 176.3(4) . . . . ?
C14 N8 C10 C11 -2.0(7) . . . . ?
C15 N5 C19 N4 -176.2(4) . . . . ?
C15 N5 C19 C18 3.2(6) . . . . ?
C15 C16 C17 C18 2.0(7) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C18 C19 N4 177.0(4) . . . . ?
C17 C18 C19 N5 -2.3(7) . . . . ?
C19 N4 C20 N3 -11.6(8) . . . . ?
C19 N4 C20 C21 167.3(4) . . . . ?
C19 N5 C15 C16 -1.5(6) . . . . ?
C20 N3 C24 C23 -0.6(7) . . . . ?
C20 N4 C19 N5 11.4(7) . . . . ?
C20 N4 C19 C18 -168.0(5) . . . . ?
C20 C21 C22 C23 2.7(8) . . . . ?
C21 C22 C23 C24 -2.7(8) . . . . ?
C22 C23 C24 N3 1.7(7) . . . . ?
C24 N3 C20 N4 179.3(4) . . . . ?
C24 N3 C20 C21 0.5(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_twin_special_details            
;
Component 2 rotated by 6.2171° 
around [0.99 0.06 0.14] (reciprocal) or [0.95 0.14 0.29] (direct)
;
# start Validation Reply Form
_vrf_PLAT026_Compound_III        
;
 PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        38% Check
RESPONSE: 
Since the crystals of the compound are of poor quality and twins,
the diffraction intensities are quite weak.
This error is probably due to weak diffraction data set. 
;
_vrf_PLAT420_Compound_III        
;
 PROBLEM: D-H Bond Without Acceptor  O2W      --H2WA   .  Please Check 
RESPONSE: 
O2w and O3w have been observed as disordered due to their very 
high average Ueq values. 
As a result, it affected the orientation of the H2WA atom.
;
_vrf_PLAT910_Compound_III        
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min). 11 Note
RESPONSE: 
This error may be caused by the small distance between the detector 
and the sample during experiment. There are only 11 missing low 
angle reflections in the FCF file. Data completeness for this structure
 is 96.4%, which is enough for a good quality refinement of data.
;
####################################################################### 
# 
# 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_Compound_V
_database_code_depnum_ccdc_archive 'CCDC 2158100'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H13 Cl Cu F N5 O2'
_chemical_formula_sum            'C19 H13 Cl Cu F N5 O2'
_chemical_formula_weight         461.33
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C19 H13 Cl Cu F N5 O2'
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           14
_space_group_name_H-M_alt        'P 21/n'
_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                   11.6071(9)
_cell_length_b                   13.0317(14)
_cell_length_c                   12.3107(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.472(8)
_cell_angle_gamma                90
_cell_volume                     1861.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2403
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      27.0360
_cell_measurement_theta_min      3.8400
_shelx_estimated_absorpt_T_max   0.695
_shelx_estimated_absorpt_T_min   0.594
_exptl_absorpt_coefficient_mu    1.354
_exptl_absorpt_correction_T_max  0.769
_exptl_absorpt_correction_T_min  0.666
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             932
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 11 -14 0.1356
11 -10 8 0.1982
16 -4 0 0.1773
7 -7 -15 0.1495
13 10 -5 0.1629
9 14 4 0.1954
-11 0 13 0.1644
-16 0 5 0.1087
11 -13 -3 0.1341
-7 17 -1 0.1974
-1 0 17 0.2157
1 0 -17 0.1210
15 6 3 0.1786
-14 10 2 0.1309
13 -12 1 0.1468
6 -15 7 0.2135
-11 -14 1 0.2123
2 10 14 0.2183
-8 5 -14 0.1681
-14 0 10 0.1384
15 8 2 0.1641
-3 2 17 0.1981
-15 -5 5 0.1311
6 17 2 0.1957
12 2 11 0.2211
-8 -7 -14 0.1952

_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.367
_exptl_crystal_size_min          0.29
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
1.9921 11.0052 -13.9701 0.2013 0.7128 0.6845
10.9983 -10.0296 7.9800 -0.2311 -0.9507 0.1402
15.9922 -4.0367 -0.0024 -0.1820 -0.6793 0.7128
6.9824 -6.9765 -14.9973 0.7327 -0.1657 0.6998
12.9948 9.9586 -4.9763 -0.3656 0.1092 0.9218
9.0052 13.9443 4.0217 -0.8026 0.1940 0.5087
-10.9852 0.0030 12.9865 -0.3411 0.0526 -0.9301
-15.9897 0.0330 4.9918 0.0985 0.3988 -0.9239
10.9883 -13.0021 -3.0159 0.3369 -0.8193 0.4368
-6.9915 16.9929 -0.9733 -0.3742 0.9479 -0.0641
-0.9859 -0.0322 16.9858 -0.7073 -0.3617 -0.5724
0.9859 0.0322 -16.9858 0.7073 0.3617 0.5724
14.9989 5.9433 3.0111 -0.6164 -0.3051 0.7144
-13.9891 10.0172 2.0111 -0.1379 0.8155 -0.5929
12.9911 -12.0174 0.9830 0.0943 -0.9352 0.4239
5.9975 -15.0058 6.9714 0.0721 -0.9725 -0.1406
-11.0003 -13.9492 0.9736 0.6278 -0.2455 -0.7591
2.0144 9.9493 14.0053 -0.9633 0.0228 -0.1934
-8.0063 5.0421 -13.9824 0.5919 0.7875 0.1181
-13.9865 0.0173 9.9882 -0.1543 0.2186 -0.9819
14.9989 7.9421 2.0152 -0.6388 -0.1996 0.7737
-2.9843 1.9699 16.9885 -0.7334 -0.2151 -0.6402
-14.9921 -4.9614 4.9840 0.2418 0.1609 -0.9469
6.0059 16.9516 2.0275 -0.7562 0.4603 0.4687
12.0050 1.9416 10.9973 -0.7697 -0.5586 0.2664
-8.0109 -6.9380 -14.0019 0.9827 0.2937 -0.0526

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7139
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.126
_diffrn_ambient_temperature      295(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      5.00  49.00   1.00   10.10    --   20.23 -99.00  90.00   44
  2  ω    -21.00  11.00   1.00   10.10    --  -22.26 -99.00 -30.00   32
  3  ω    -20.00  21.00   1.00   10.10    --  -22.26 -99.00-180.00   41
  4  ω    -95.00  20.00   1.00   10.10    --  -22.26   0.00   0.00  115
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0196027000
_diffrn_orient_matrix_UB_12      -0.0325403000
_diffrn_orient_matrix_UB_13      -0.0428423000
_diffrn_orient_matrix_UB_21      -0.0320613000
_diffrn_orient_matrix_UB_22      0.0412717000
_diffrn_orient_matrix_UB_23      -0.0230796000
_diffrn_orient_matrix_UB_31      0.0481716000
_diffrn_orient_matrix_UB_32      0.0142783000
_diffrn_orient_matrix_UB_33      -0.0308781000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2856
_reflns_number_total             3800
_reflns_odcompleteness_completeness 99.77
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.479
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.077
_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)+(0.0449P)²+0.2973P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1032
_refine_ls_wR_factor_ref         0.1142
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19)
;
_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 0.78715(3) 0.71910(3) 0.56840(3) 0.03063(15) Uani 1 1 d . . . . .
Cl1 Cl 0.83116(8) 0.72231(8) 0.37067(7) 0.0437(3) Uani 1 1 d . . . . .
F1 F 0.42938(19) 0.9103(2) 0.37948(18) 0.0752(9) Uani 1 1 d . . . . .
O1 O 0.6111(2) 0.7218(2) 0.72591(19) 0.0449(7) Uani 1 1 d . . . . .
O2 O 0.3108(2) 0.8940(3) 0.5702(2) 0.0678(10) Uani 1 1 d . . . . .
N1 N 0.6291(2) 0.7704(2) 0.5512(2) 0.0318(7) Uani 1 1 d . . . . .
N2 N 0.4615(2) 0.8055(2) 0.6444(2) 0.0378(7) Uani 1 1 d . . . . .
H2 H 0.423630 0.798261 0.703029 0.045 Uiso 1 1 calc R U . . .
N3 N 0.8666(2) 0.8554(2) 0.6061(2) 0.0342(7) Uani 1 1 d . . . . .
N4 N 0.9374(2) 0.6699(2) 0.6190(2) 0.0314(6) Uani 1 1 d . . . . .
N5 N 0.7566(3) 0.5631(2) 0.5825(2) 0.0392(7) Uani 1 1 d . . . . .
C1 C 0.5713(3) 0.7634(3) 0.6447(3) 0.0308(8) Uani 1 1 d . . . . .
C2 C 0.4062(3) 0.8576(3) 0.5609(3) 0.0410(9) Uani 1 1 d . . . . .
C3 C 0.4758(3) 0.8613(3) 0.4666(3) 0.0411(9) Uani 1 1 d . . . . .
C4 C 0.5803(3) 0.8198(3) 0.4655(3) 0.0380(9) Uani 1 1 d . . . . .
H4 H 0.622067 0.825058 0.402251 0.046 Uiso 1 1 calc R U . . .
C5 C 0.8220(3) 0.9492(3) 0.6013(3) 0.0452(10) Uani 1 1 d . . . . .
H5 H 0.744285 0.956238 0.582485 0.054 Uiso 1 1 calc R U . . .
C6 C 0.8853(4) 1.0362(3) 0.6226(3) 0.0530(11) Uani 1 1 d . . . . .
H6 H 0.850910 1.100550 0.618913 0.064 Uiso 1 1 calc R U . . .
C7 C 0.9994(4) 1.0265(3) 0.6494(3) 0.0557(11) Uani 1 1 d . . . . .
H7 H 1.043814 1.084436 0.664515 0.067 Uiso 1 1 calc R U . . .
C8 C 1.0483(3) 0.9307(3) 0.6537(3) 0.0475(10) Uani 1 1 d . . . . .
H8 H 1.126502 0.923111 0.670301 0.057 Uiso 1 1 calc R U . . .
C9 C 0.9803(3) 0.8455(3) 0.6333(3) 0.0344(8) Uani 1 1 d . . . . .
C10 C 1.0206(3) 0.7389(3) 0.6391(3) 0.0342(8) Uani 1 1 d . . . . .
C11 C 1.1309(3) 0.7068(3) 0.6668(3) 0.0471(10) Uani 1 1 d . . . . .
H11 H 1.189223 0.754128 0.681381 0.056 Uiso 1 1 calc R U . . .
C12 C 1.1521(3) 0.6029(4) 0.6721(3) 0.0505(11) Uani 1 1 d . . . . .
H12 H 1.226373 0.579994 0.688748 0.061 Uiso 1 1 calc R U . . .
C13 C 1.0656(3) 0.5324(3) 0.6534(3) 0.0454(10) Uani 1 1 d . . . . .
H13 H 1.080040 0.462408 0.658827 0.054 Uiso 1 1 calc R U . . .
C14 C 0.9562(3) 0.5689(3) 0.6263(3) 0.0345(8) Uani 1 1 d . . . . .
C15 C 0.8516(3) 0.5077(3) 0.6070(3) 0.0353(8) Uani 1 1 d . . . . .
C16 C 0.8477(4) 0.4021(3) 0.6175(3) 0.0508(10) Uani 1 1 d . . . . .
H16 H 0.914370 0.365013 0.633771 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7444(4) 0.3532(3) 0.6035(4) 0.0638(12) Uani 1 1 d . . . . .
H17 H 0.739993 0.282223 0.610172 0.077 Uiso 1 1 calc R U . . .
C18 C 0.6470(4) 0.4096(4) 0.5795(4) 0.0669(13) Uani 1 1 d . . . . .
H18 H 0.575746 0.377602 0.570811 0.080 Uiso 1 1 calc R U . . .
C19 C 0.6571(4) 0.5147(3) 0.5687(3) 0.0534(11) Uani 1 1 d . . . . .
H19 H 0.591493 0.552874 0.551014 0.064 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 Cl1 2.5004(9) . ?
Cu1 N1 1.959(3) . ?
Cu1 N3 2.049(3) . ?
Cu1 N4 1.946(3) . ?
Cu1 N5 2.072(3) . ?
F1 C3 1.348(4) . ?
O1 C1 1.218(4) . ?
O2 C2 1.213(4) . ?
N1 C1 1.350(4) . ?
N1 C4 1.348(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.387(4) . ?
N2 C2 1.376(4) . ?
N3 C5 1.329(5) . ?
N3 C9 1.359(4) . ?
N4 C10 1.338(4) . ?
N4 C14 1.337(4) . ?
N5 C15 1.345(4) . ?
N5 C19 1.324(5) . ?
C2 C3 1.432(5) . ?
C3 C4 1.329(5) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.373(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.362(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.373(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(5) . ?
C9 C10 1.467(5) . ?
C10 C11 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.378(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(5) . ?
C14 C15 1.467(5) . ?
C15 C16 1.383(5) . ?
C16 H16 0.9300 . ?
C16 C17 1.365(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(6) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(6) . ?
C19 H19 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
N1 Cu1 Cl1 95.94(8) . . ?
N1 Cu1 N3 98.25(12) . . ?
N1 Cu1 N5 100.52(12) . . ?
N3 Cu1 Cl1 95.98(8) . . ?
N3 Cu1 N5 155.29(11) . . ?
N4 Cu1 Cl1 96.49(8) . . ?
N4 Cu1 N1 167.54(11) . . ?
N4 Cu1 N3 79.53(12) . . ?
N4 Cu1 N5 78.67(12) . . ?
N5 Cu1 Cl1 97.91(8) . . ?
C1 N1 Cu1 111.7(2) . . ?
C4 N1 Cu1 128.4(2) . . ?
C4 N1 C1 119.4(3) . . ?
C1 N2 H2 116.3 . . ?
C2 N2 H2 116.3 . . ?
C2 N2 C1 127.4(3) . . ?
C5 N3 Cu1 127.9(3) . . ?
C5 N3 C9 118.2(3) . . ?
C9 N3 Cu1 113.7(2) . . ?
C10 N4 Cu1 118.3(2) . . ?
C14 N4 Cu1 119.3(3) . . ?
C14 N4 C10 122.2(3) . . ?
C15 N5 Cu1 113.8(2) . . ?
C19 N5 Cu1 127.4(3) . . ?
C19 N5 C15 118.8(3) . . ?
O1 C1 N1 122.9(3) . . ?
O1 C1 N2 120.5(3) . . ?
N1 C1 N2 116.6(3) . . ?
O2 C2 N2 122.1(3) . . ?
O2 C2 C3 126.7(3) . . ?
N2 C2 C3 111.1(3) . . ?
F1 C3 C2 116.0(3) . . ?
C4 C3 F1 122.1(3) . . ?
C4 C3 C2 121.9(3) . . ?
N1 C4 H4 118.3 . . ?
C3 C4 N1 123.5(3) . . ?
C3 C4 H4 118.3 . . ?
N3 C5 H5 118.5 . . ?
N3 C5 C6 123.0(4) . . ?
C6 C5 H5 118.5 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.9(4) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.5(4) . . ?
C8 C7 H7 120.3 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.3(4) . . ?
C9 C8 H8 120.3 . . ?
N3 C9 C8 121.0(3) . . ?
N3 C9 C10 114.1(3) . . ?
C8 C9 C10 124.9(3) . . ?
N4 C10 C9 113.6(3) . . ?
N4 C10 C11 120.2(4) . . ?
C11 C10 C9 126.2(4) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(4) . . ?
C12 C11 H11 120.9 . . ?
C11 C12 H12 119.4 . . ?
C13 C12 C11 121.3(4) . . ?
C13 C12 H12 119.4 . . ?
C12 C13 H13 120.9 . . ?
C12 C13 C14 118.1(4) . . ?
C14 C13 H13 120.9 . . ?
N4 C14 C13 119.9(4) . . ?
N4 C14 C15 113.0(3) . . ?
C13 C14 C15 127.0(3) . . ?
N5 C15 C14 114.5(3) . . ?
N5 C15 C16 121.7(4) . . ?
C16 C15 C14 123.7(3) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 118.9(4) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.5(4) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 120.7 . . ?
C17 C18 C19 118.7(4) . . ?
C19 C18 H18 120.7 . . ?
N5 C19 C18 122.3(4) . . ?
N5 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 Cl1 0.86 2.37 3.224(3) 176.3 4_576 yes

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 N1 C1 O1 -5.9(4) . . . . ?
Cu1 N1 C1 N2 174.8(2) . . . . ?
Cu1 N1 C4 C3 -172.5(3) . . . . ?
Cu1 N3 C5 C6 -176.1(3) . . . . ?
Cu1 N3 C9 C8 175.5(3) . . . . ?
Cu1 N3 C9 C10 -4.9(4) . . . . ?
Cu1 N4 C10 C9 7.7(4) . . . . ?
Cu1 N4 C10 C11 -174.9(2) . . . . ?
Cu1 N4 C14 C13 174.6(2) . . . . ?
Cu1 N4 C14 C15 -7.4(4) . . . . ?
Cu1 N5 C15 C14 4.0(4) . . . . ?
Cu1 N5 C15 C16 -178.8(3) . . . . ?
Cu1 N5 C19 C18 179.6(3) . . . . ?
F1 C3 C4 N1 179.9(4) . . . . ?
O2 C2 C3 F1 -0.3(7) . . . . ?
O2 C2 C3 C4 179.1(4) . . . . ?
N2 C2 C3 F1 179.7(3) . . . . ?
N2 C2 C3 C4 -1.0(6) . . . . ?
N3 C5 C6 C7 0.5(6) . . . . ?
N3 C9 C10 N4 -1.4(4) . . . . ?
N3 C9 C10 C11 -178.7(3) . . . . ?
N4 C10 C11 C12 0.4(5) . . . . ?
N4 C14 C15 N5 1.7(4) . . . . ?
N4 C14 C15 C16 -175.4(3) . . . . ?
N5 C15 C16 C17 -0.6(6) . . . . ?
C1 N1 C4 C3 -1.3(6) . . . . ?
C1 N2 C2 O2 -177.9(4) . . . . ?
C1 N2 C2 C3 2.2(5) . . . . ?
C2 N2 C1 O1 177.7(4) . . . . ?
C2 N2 C1 N1 -2.9(5) . . . . ?
C2 C3 C4 N1 0.6(7) . . . . ?
C4 N1 C1 O1 -178.4(3) . . . . ?
C4 N1 C1 N2 2.2(5) . . . . ?
C5 N3 C9 C8 -1.0(5) . . . . ?
C5 N3 C9 C10 178.6(3) . . . . ?
C5 C6 C7 C8 0.3(6) . . . . ?
C6 C7 C8 C9 -1.4(6) . . . . ?
C7 C8 C9 N3 1.8(6) . . . . ?
C7 C8 C9 C10 -177.7(3) . . . . ?
C8 C9 C10 N4 178.1(3) . . . . ?
C8 C9 C10 C11 0.9(6) . . . . ?
C9 N3 C5 C6 -0.2(5) . . . . ?
C9 C10 C11 C12 177.5(3) . . . . ?
C10 N4 C14 C13 -1.4(5) . . . . ?
C10 N4 C14 C15 176.7(3) . . . . ?
C10 C11 C12 C13 -1.7(6) . . . . ?
C11 C12 C13 C14 1.5(6) . . . . ?
C12 C13 C14 N4 0.0(5) . . . . ?
C12 C13 C14 C15 -177.7(3) . . . . ?
C13 C14 C15 N5 179.6(3) . . . . ?
C13 C14 C15 C16 2.5(5) . . . . ?
C14 N4 C10 C9 -176.3(3) . . . . ?
C14 N4 C10 C11 1.1(5) . . . . ?
C14 C15 C16 C17 176.3(4) . . . . ?
C15 N5 C19 C18 0.6(6) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
C16 C17 C18 C19 0.9(7) . . . . ?
C17 C18 C19 N5 -1.3(7) . . . . ?
C19 N5 C15 C14 -176.9(3) . . . . ?
C19 N5 C15 C16 0.3(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 1.123
_oxdiff_exptl_absorpt_empirical_full_min 0.886
####################################################################### 
# 
# 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_Compound_I
_database_code_depnum_ccdc_archive 'CCDC 2158098'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 Cl Cu F N4 O3 S'
_chemical_formula_sum            'C16 H16 Cl Cu F N4 O3 S'
_chemical_formula_weight         462.38
_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'
S S 0.1246 0.1234 '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        P21/n
_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                   8.1412(4)
_cell_length_b                   21.3384(13)
_cell_length_c                   11.1897(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.746(4)
_cell_angle_gamma                90
_cell_volume                     1939.72(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1106
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      22.8250
_cell_measurement_theta_min      3.3880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.405
_exptl_absorpt_correction_T_max  0.933
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             940
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-11 0 -1 0.0791
-2 27 6 0.0334
-11 5 5 0.0793
0 29 5 0.0346
-3 10 14 0.0763
0 30 -2 0.0362
11 -7 4 0.0840
0 15 -14 0.0773
-3 -14 14 0.0730
11 -6 -1 0.1005
-1 -26 -8 0.0541
0 -30 2 0.0181

_exptl_crystal_size_max          0.204
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.054
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_av_unetI/netI     0.0978
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6500
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.151
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 16.1333
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  52.00   1.00   15.46    --  -16.00  37.00  30.00   86
  2  ω    -82.00  -1.00   1.00   15.46    --  -16.00 -57.00-120.00   81
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2035
_reflns_number_total             3397
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     250
_refine_ls_number_reflns         3397
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.006
_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)+(0.0247P)²+0.1894P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid body (RIGU) restrains
 S1, O3
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.33188(7) 0.37865(3) 0.33114(5) 0.0384(2) Uani 1 1 d . . . . .
Cl1 Cl 0.09592(15) 0.30867(6) 0.37156(11) 0.0533(4) Uani 1 1 d . . . . .
S1 S 0.50936(16) 0.28401(7) 0.16202(13) 0.0569(4) Uani 1 1 d . . . . .
F1 F -0.0797(4) 0.37793(19) -0.0564(3) 0.1202(15) Uani 1 1 d . . . . .
O1 O 0.4908(4) 0.46147(14) 0.1449(3) 0.0481(9) Uani 1 1 d . . . . .
O2 O 0.1206(4) 0.4561(2) -0.1770(3) 0.0867(14) Uani 1 1 d . . . . .
O3 O 0.4970(4) 0.31588(16) 0.2815(3) 0.0644(10) Uani 1 1 d . . . . .
N1 N 0.2595(5) 0.40302(17) 0.1635(3) 0.0411(10) Uani 1 1 d . . . . .
N2 N 0.3013(5) 0.45838(19) -0.0127(3) 0.0406(11) Uani 1 1 d . . . . .
H2 H 0.359(6) 0.487(2) -0.048(4) 0.057(17) Uiso 1 1 d . . . . .
N3 N 0.4367(4) 0.36684(17) 0.4975(3) 0.0356(9) Uani 1 1 d . . . . .
N4 N 0.2624(4) 0.45911(16) 0.4083(3) 0.0329(9) Uani 1 1 d . . . . .
C1 C 0.3560(6) 0.4414(2) 0.1028(4) 0.0382(12) Uani 1 1 d . . . . .
C2 C 0.1564(6) 0.4395(3) -0.0747(5) 0.0551(15) Uani 1 1 d . . . . .
C3 C 0.0639(6) 0.3999(3) -0.0040(5) 0.0665(17) Uani 1 1 d . . . . .
C4 C 0.1141(6) 0.3832(2) 0.1076(4) 0.0583(15) Uani 1 1 d . . . . .
H4 H 0.046943 0.356934 0.149336 0.070 Uiso 1 1 calc R U . . .
C5 C 0.5192(6) 0.3159(2) 0.5366(5) 0.0501(14) Uani 1 1 d . . . . .
H5 H 0.534452 0.283429 0.482969 0.060 Uiso 1 1 calc R U . . .
C6 C 0.5822(6) 0.3096(2) 0.6523(5) 0.0553(15) Uani 1 1 d . . . . .
H6 H 0.639344 0.273664 0.676813 0.066 Uiso 1 1 calc R U . . .
C7 C 0.5596(6) 0.3571(3) 0.7309(5) 0.0603(16) Uani 1 1 d . . . . .
H7 H 0.600887 0.353598 0.810109 0.072 Uiso 1 1 calc R U . . .
C8 C 0.4752(5) 0.4104(2) 0.6929(4) 0.0460(13) Uani 1 1 d . . . . .
H8 H 0.459675 0.443262 0.745555 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4140(5) 0.4137(2) 0.5742(4) 0.0325(11) Uani 1 1 d . . . . .
C10 C 0.3153(5) 0.4664(2) 0.5243(4) 0.0304(11) Uani 1 1 d . . . . .
C11 C 0.2775(5) 0.5190(2) 0.5880(4) 0.0405(12) Uani 1 1 d . . . . .
H11 H 0.317638 0.523551 0.667219 0.049 Uiso 1 1 calc R U . . .
C12 C 0.1794(6) 0.5650(2) 0.5336(5) 0.0513(14) Uani 1 1 d . . . . .
H12 H 0.153219 0.600865 0.575606 0.062 Uiso 1 1 calc R U . . .
C13 C 0.1214(6) 0.5570(2) 0.4168(5) 0.0499(14) Uani 1 1 d . . . . .
H13 H 0.052844 0.586746 0.378760 0.060 Uiso 1 1 calc R U . . .
C14 C 0.1667(5) 0.5038(2) 0.3568(4) 0.0432(13) Uani 1 1 d . . . . .
H14 H 0.129110 0.498857 0.277043 0.052 Uiso 1 1 calc R U . . .
C15 C 0.6843(7) 0.3162(3) 0.1045(6) 0.093(2) Uani 1 1 d . . . . .
H15A H 0.666742 0.360053 0.089373 0.140 Uiso 1 1 calc R U . . .
H15B H 0.705826 0.295401 0.031043 0.140 Uiso 1 1 calc R U . . .
H15C H 0.776801 0.310878 0.161309 0.140 Uiso 1 1 calc R U . . .
C16 C 0.5908(8) 0.2092(2) 0.1998(6) 0.102(2) Uani 1 1 d . . . . .
H16A H 0.685478 0.213757 0.254831 0.152 Uiso 1 1 calc R U . . .
H16B H 0.622231 0.188453 0.128573 0.152 Uiso 1 1 calc R U . . .
H16C H 0.508850 0.184646 0.236318 0.152 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 Cl1 2.498(2) . ?
Cu1 O3 2.002(3) . ?
Cu1 N1 1.998(3) . ?
Cu1 N3 2.012(3) . ?
Cu1 N4 2.019(3) . ?
S1 O3 1.509(3) . ?
S1 C15 1.742(5) . ?
S1 C16 1.770(5) . ?
F1 C3 1.356(5) . ?
O1 C1 1.242(5) . ?
O2 C2 1.215(5) . ?
N1 C1 1.348(5) . ?
N1 C4 1.369(5) . ?
N2 H2 0.88(5) . ?
N2 C1 1.388(5) . ?
N2 C2 1.389(5) . ?
N3 C5 1.336(5) . ?
N3 C9 1.338(5) . ?
N4 C10 1.350(5) . ?
N4 C14 1.338(5) . ?
C2 C3 1.410(7) . ?
C3 C4 1.337(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.368(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.361(7) . ?
C7 H7 0.9300 . ?
C7 C8 1.381(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(6) . ?
C9 C10 1.471(6) . ?
C10 C11 1.375(6) . ?
C11 H11 0.9300 . ?
C11 C12 1.381(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(6) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
O3 Cu1 Cl1 100.87(11) . . ?
O3 Cu1 N3 85.48(14) . . ?
O3 Cu1 N4 154.09(14) . . ?
N1 Cu1 Cl1 98.20(12) . . ?
N1 Cu1 O3 94.35(14) . . ?
N1 Cu1 N3 169.21(15) . . ?
N1 Cu1 N4 96.10(15) . . ?
N3 Cu1 Cl1 92.42(10) . . ?
N3 Cu1 N4 79.90(15) . . ?
N4 Cu1 Cl1 101.00(10) . . ?
O3 S1 C15 104.7(3) . . ?
O3 S1 C16 103.9(2) . . ?
C15 S1 C16 98.1(3) . . ?
S1 O3 Cu1 129.22(19) . . ?
C1 N1 Cu1 119.0(3) . . ?
C1 N1 C4 118.2(4) . . ?
C4 N1 Cu1 122.8(3) . . ?
C1 N2 H2 117(3) . . ?
C1 N2 C2 126.9(5) . . ?
C2 N2 H2 116(3) . . ?
C5 N3 Cu1 125.3(3) . . ?
C5 N3 C9 119.0(4) . . ?
C9 N3 Cu1 115.6(3) . . ?
C10 N4 Cu1 115.4(3) . . ?
C14 N4 Cu1 126.4(3) . . ?
C14 N4 C10 118.2(4) . . ?
O1 C1 N1 123.2(4) . . ?
O1 C1 N2 119.0(5) . . ?
N1 C1 N2 117.8(4) . . ?
O2 C2 N2 122.1(5) . . ?
O2 C2 C3 126.8(5) . . ?
N2 C2 C3 111.2(4) . . ?
F1 C3 C2 116.2(4) . . ?
C4 C3 F1 121.0(5) . . ?
C4 C3 C2 122.8(5) . . ?
N1 C4 H4 118.4 . . ?
C3 C4 N1 123.2(5) . . ?
C3 C4 H4 118.4 . . ?
N3 C5 H5 118.7 . . ?
N3 C5 C6 122.6(5) . . ?
C6 C5 H5 118.7 . . ?
C5 C6 H6 120.6 . . ?
C7 C6 C5 118.8(5) . . ?
C7 C6 H6 120.6 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(5) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.8 . . ?
C7 C8 C9 118.4(5) . . ?
C9 C8 H8 120.8 . . ?
N3 C9 C8 121.3(4) . . ?
N3 C9 C10 115.0(4) . . ?
C8 C9 C10 123.6(4) . . ?
N4 C10 C9 114.1(4) . . ?
N4 C10 C11 121.6(4) . . ?
C11 C10 C9 124.3(4) . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.7(5) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 120.5 . . ?
C13 C12 C11 119.0(5) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.7(5) . . ?
C14 C13 H13 120.7 . . ?
N4 C14 C13 122.9(4) . . ?
N4 C14 H14 118.6 . . ?
C13 C14 H14 118.6 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.88(5) 2.01(5) 2.882(5) 169(4) 3_665 yes

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 N1 C1 O1 1.7(6) . . . . ?
Cu1 N1 C1 N2 -178.9(3) . . . . ?
Cu1 N1 C4 C3 179.2(4) . . . . ?
Cu1 N3 C5 C6 -177.3(4) . . . . ?
Cu1 N3 C9 C8 177.8(3) . . . . ?
Cu1 N3 C9 C10 0.1(5) . . . . ?
Cu1 N4 C10 C9 -0.4(4) . . . . ?
Cu1 N4 C10 C11 179.9(3) . . . . ?
Cu1 N4 C14 C13 178.3(3) . . . . ?
F1 C3 C4 N1 178.6(5) . . . . ?
O2 C2 C3 F1 0.2(9) . . . . ?
O2 C2 C3 C4 178.9(6) . . . . ?
N2 C2 C3 F1 -179.2(5) . . . . ?
N2 C2 C3 C4 -0.5(8) . . . . ?
N3 C5 C6 C7 0.2(8) . . . . ?
N3 C9 C10 N4 0.2(5) . . . . ?
N3 C9 C10 C11 179.9(4) . . . . ?
N4 C10 C11 C12 1.7(7) . . . . ?
C1 N1 C4 C3 0.3(8) . . . . ?
C1 N2 C2 O2 -178.5(5) . . . . ?
C1 N2 C2 C3 0.9(7) . . . . ?
C2 N2 C1 O1 178.7(4) . . . . ?
C2 N2 C1 N1 -0.7(7) . . . . ?
C2 C3 C4 N1 0.0(9) . . . . ?
C4 N1 C1 O1 -179.3(4) . . . . ?
C4 N1 C1 N2 0.1(6) . . . . ?
C5 N3 C9 C8 0.3(6) . . . . ?
C5 N3 C9 C10 -177.3(4) . . . . ?
C5 C6 C7 C8 -0.4(8) . . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 N3 -0.5(7) . . . . ?
C7 C8 C9 C10 176.9(4) . . . . ?
C8 C9 C10 N4 -177.4(4) . . . . ?
C8 C9 C10 C11 2.3(7) . . . . ?
C9 N3 C5 C6 -0.1(7) . . . . ?
C9 C10 C11 C12 -177.9(4) . . . . ?
C10 N4 C14 C13 0.6(7) . . . . ?
C10 C11 C12 C13 0.2(7) . . . . ?
C11 C12 C13 C14 -1.7(7) . . . . ?
C12 C13 C14 N4 1.3(7) . . . . ?
C14 N4 C10 C9 177.6(4) . . . . ?
C14 N4 C10 C11 -2.1(6) . . . . ?
C15 S1 O3 Cu1 110.2(3) . . . . ?
C16 S1 O3 Cu1 -147.4(3) . . . . ?

_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
;
####################################################################### 
# 
# 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_Compound_IV
_database_code_depnum_ccdc_archive 'CCDC 2158097'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H15 Cu F N6 O5, H2 O'
_chemical_formula_sum            'C16 H17 Cu F N6 O6'
_chemical_formula_weight         471.89
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   7.8385(7)
_cell_length_b                   8.4548(9)
_cell_length_c                   15.5138(10)
_cell_angle_alpha                84.255(7)
_cell_angle_beta                 77.099(7)
_cell_angle_gamma                70.084(9)
_cell_volume                     941.93(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2123
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      25.2950
_cell_measurement_theta_min      3.6450
_shelx_estimated_absorpt_T_max   0.838
_shelx_estimated_absorpt_T_min   0.661
_exptl_absorpt_coefficient_mu    1.218
_exptl_absorpt_correction_T_max  0.868
_exptl_absorpt_correction_T_min  0.726
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.664
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             482
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 0 -21 0.0892
4 0 21 0.0892
-8 -11 -2 0.1574
8 11 2 0.1574
-10 0 3 0.0764
9 -2 -3 0.0804
10 1 7 0.0836
-10 0 -7 0.0902
3 -10 4 0.1639
2 12 -1 0.1832
-10 1 -1 0.0670
-9 -8 -12 0.1256
0 0 -21 0.0805
8 2 -11 0.0866
4 11 9 0.1664
10 0 1 0.0711
-10 -8 -3 0.1266
9 9 8 0.1224
-5 -1 17 0.0887
10 0 11 0.0825
-1 -7 -18 0.1408

_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6029
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_min         3.129
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  82.00   1.00    3.00    --   14.20 178.00  60.00   43
  2  ω    -85.00   1.00   1.00    3.00    --  -16.23 -37.00  90.00   86
  3  ω    -38.00   9.00   1.00    3.00    --  -16.23 -77.00   0.00   47
  4  ω    -38.00   9.00   1.00    3.00    --  -16.23 -77.00-120.00   47
  5  ω    -38.00  53.00   1.00    3.00    --  -16.23  19.00 -90.00   91
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2130
_reflns_number_total             3421
_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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.318
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.856
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         3421
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0745
_refine_ls_R_factor_gt           0.0436
_refine_ls_restrained_S_all      0.865
_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)+(0.0373P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0851
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H) groups
2. Restrained distances
 O1W-H1WB
 0.85 with sigma of 0.02
 O1W-H1WA
 0.85 with sigma of 0.02
 N6-O4 \\sim N6-O5B
 with sigma of 0.02
 N4A-C10 \\sim N4B-C10
 with sigma of 0.02
 Cu1-N4A \\sim Cu1-N4B
 with sigma of 0.02
 C11-N4A \\sim C11-N4B
 with sigma of 0.02
3. Others
 Sof(O5B)=1-FVAR(1)
 Sof(O4)=FVAR(1)
 Sof(N4B)=Sof(H4B)=Sof(H10C)=Sof(H10D)=Sof(H11C)=Sof(H11D)=1-FVAR(2)
 Sof(N4A)=Sof(H4A)=Sof(H10A)=Sof(H10B)=Sof(H11A)=Sof(H11B)=FVAR(2)
4.a Riding coordinates:
 O1W(H1WA,H1WB)
4.b Ternary CH refined with riding coordinates:
 N4A(H4A), N4B(H4B)
4.c Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C10(H10C,H10D), C11(H11A,H11B), C11(H11C,H11D)
4.d Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.52222(6) 0.69861(6) 0.76112(3) 0.03966(17) Uani 1 1 d D . . . .
F1 F 1.1858(3) 0.5896(4) 0.54661(15) 0.1002(10) Uani 1 1 d . . . . .
O1 O 0.4553(3) 0.8958(3) 0.59983(14) 0.0472(6) Uani 1 1 d . . . . .
O2 O 1.0256(3) 0.8185(4) 0.42505(17) 0.0839(10) Uani 1 1 d . . . . .
O3 O 0.7524(4) 0.4950(4) 0.8237(2) 0.0879(10) Uani 1 1 d . . . . .
O4 O 0.6018(9) 0.5131(8) 0.9585(3) 0.079(3) Uani 0.518(8) 1 d D . P A 1
O5A O 0.8754(5) 0.3436(5) 0.9267(2) 0.0997(12) Uani 1 1 d . . . . .
O5B O 0.7439(12) 0.5956(10) 0.9349(5) 0.108(4) Uani 0.482(8) 1 d D . P A 2
N1 N 0.7007(4) 0.7154(3) 0.65142(16) 0.0358(7) Uani 1 1 d . . . . .
N2 N 0.7424(3) 0.8563(3) 0.51486(16) 0.0393(7) Uani 1 1 d . . . . .
H2 H 0.691271 0.927573 0.476941 0.047 Uiso 1 1 calc R U . . .
N3 N 0.5224(4) 0.8995(4) 0.81820(18) 0.0467(8) Uani 1 1 d . . . . .
N4A N 0.3143(6) 0.7050(7) 0.8650(4) 0.0429(15) Uani 0.797(11) 1 d D . P B 1
H4A H 0.370960 0.637026 0.912642 0.052 Uiso 0.797(11) 1 calc R U P B 1
N4B N 0.2563(18) 0.775(2) 0.8242(10) 0.024(5) Uani 0.203(11) 1 d D . P B 2
H4B H 0.185380 0.846514 0.781826 0.028 Uiso 0.203(11) 1 calc R U P B 2
N5 N 0.4466(4) 0.5202(3) 0.72319(17) 0.0359(7) Uani 1 1 d . . . . .
N6 N 0.7648(5) 0.4674(6) 0.9002(3) 0.0639(10) Uani 1 1 d D . . . .
C1 C 0.6263(5) 0.8239(4) 0.5905(2) 0.0344(8) Uani 1 1 d . . . . .
C2 C 0.9318(5) 0.7855(5) 0.4945(2) 0.0519(10) Uani 1 1 d . . . . .
C3 C 1.0003(5) 0.6687(5) 0.5613(2) 0.0575(11) Uani 1 1 d . . . . .
C4 C 0.8894(5) 0.6375(5) 0.6347(2) 0.0516(10) Uani 1 1 d . . . . .
H4 H 0.941875 0.559863 0.676231 0.062 Uiso 1 1 calc R U . . .
C5 C 0.6576(6) 0.9679(5) 0.8011(3) 0.0585(11) Uani 1 1 d . . . . .
H5 H 0.762242 0.921134 0.757963 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6470(7) 1.1035(6) 0.8448(3) 0.0741(14) Uani 1 1 d . . . . .
H6 H 0.742922 1.148770 0.831521 0.089 Uiso 1 1 calc R U . . .
C7 C 0.4947(8) 1.1721(5) 0.9079(3) 0.0707(14) Uani 1 1 d . . . . .
H7 H 0.485289 1.265015 0.938333 0.085 Uiso 1 1 calc R U . . .
C8 C 0.3546(6) 1.1037(5) 0.9267(2) 0.0610(11) Uani 1 1 d . . . . .
H8 H 0.249177 1.149417 0.969670 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3737(6) 0.9644(5) 0.8800(2) 0.0459(10) Uani 1 1 d . . . . .
C10 C 0.2297(5) 0.8790(5) 0.8959(2) 0.0558(11) Uani 1 1 d D . . . .
H10A H 0.175661 0.878295 0.958550 0.067 Uiso 0.797(11) 1 calc R U P B 1
H10B H 0.131734 0.940340 0.864544 0.067 Uiso 0.797(11) 1 calc R U P B 1
H10C H 0.236773 0.810911 0.950001 0.067 Uiso 0.203(11) 1 calc R U P B 2
H10D H 0.107503 0.963192 0.903177 0.067 Uiso 0.203(11) 1 calc R U P B 2
C11 C 0.1908(5) 0.6258(5) 0.8450(2) 0.0461(10) Uani 1 1 d D . . . .
H11A H 0.086333 0.710823 0.825859 0.055 Uiso 0.797(11) 1 calc R U P B 1
H11B H 0.143701 0.569448 0.897801 0.055 Uiso 0.797(11) 1 calc R U P B 1
H11C H 0.058352 0.660333 0.847890 0.055 Uiso 0.203(11) 1 calc R U P B 2
H11D H 0.215788 0.575575 0.901815 0.055 Uiso 0.203(11) 1 calc R U P B 2
C12 C 0.2918(4) 0.5000(4) 0.7733(2) 0.0368(8) Uani 1 1 d . . . . .
C13 C 0.2303(5) 0.3730(5) 0.7576(2) 0.0432(9) Uani 1 1 d . . . . .
H13 H 0.122789 0.360108 0.792687 0.052 Uiso 1 1 calc R U . . .
C14 C 0.3285(6) 0.2670(5) 0.6901(3) 0.0538(11) Uani 1 1 d . . . . .
H14 H 0.287707 0.181197 0.679072 0.065 Uiso 1 1 calc R U . . .
C15 C 0.4876(5) 0.2857(5) 0.6382(2) 0.0531(10) Uani 1 1 d . . . . .
H15 H 0.556269 0.213574 0.592144 0.064 Uiso 1 1 calc R U . . .
C16 C 0.5413(5) 0.4146(5) 0.6569(2) 0.0481(10) Uani 1 1 d . . . . .
H16 H 0.648088 0.429439 0.622092 0.058 Uiso 1 1 calc R U . . .
O1W O 0.9068(5) 1.0682(5) 0.3026(2) 0.1032(12) Uani 1 1 d D . . . .
H1WA H 0.790351 1.106227 0.330414 0.94(18) Uiso 1 1 d DR . . . .
H1WB H 0.965831 0.975397 0.331314 0.28(5) Uiso 1 1 d DR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O3 2.344(3) . ?
Cu1 N1 1.974(2) . ?
Cu1 N3 1.993(3) . ?
Cu1 N4A 2.010(4) . ?
Cu1 N4B 2.004(11) . ?
Cu1 N5 1.979(3) . ?
F1 C3 1.354(4) . ?
O1 C1 1.250(4) . ?
O2 C2 1.227(4) . ?
O3 N6 1.205(4) . ?
O4 N6 1.348(6) . ?
O5A N6 1.213(4) . ?
O5B N6 1.204(7) . ?
N1 C1 1.335(4) . ?
N1 C4 1.374(4) . ?
N2 H2 0.8600 . ?
N2 C1 1.382(3) . ?
N2 C2 1.373(4) . ?
N3 C5 1.338(4) . ?
N3 C9 1.323(4) . ?
N4A H4A 0.9800 . ?
N4A C10 1.472(5) . ?
N4A C11 1.449(5) . ?
N4B H4B 0.9800 . ?
N4B C10 1.420(11) . ?
N4B C11 1.500(13) . ?
N5 C12 1.341(4) . ?
N5 C16 1.340(4) . ?
C2 C3 1.421(5) . ?
C3 C4 1.332(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.358(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.357(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.371(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.391(5) . ?
C9 C10 1.500(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C10 H10D 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C11 H11D 0.9700 . ?
C11 C12 1.505(5) . ?
C12 C13 1.379(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.360(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.375(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(4) . ?
C16 H16 0.9300 . ?
O1W H1WA 0.8801 . ?
O1W H1WB 0.8957 . ?

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
N1 Cu1 O3 92.24(11) . . ?
N1 Cu1 N3 96.65(11) . . ?
N1 Cu1 N4A 172.2(2) . . ?
N1 Cu1 N4B 146.0(6) . . ?
N1 Cu1 N5 97.34(11) . . ?
N3 Cu1 O3 98.00(12) . . ?
N3 Cu1 N4A 82.37(14) . . ?
N3 Cu1 N4B 81.8(3) . . ?
N4A Cu1 O3 95.5(2) . . ?
N4B Cu1 O3 121.7(6) . . ?
N5 Cu1 O3 90.40(11) . . ?
N5 Cu1 N3 163.37(12) . . ?
N5 Cu1 N4A 82.55(14) . . ?
N5 Cu1 N4B 81.6(3) . . ?
N6 O3 Cu1 129.6(3) . . ?
C1 N1 Cu1 114.4(2) . . ?
C1 N1 C4 118.2(3) . . ?
C4 N1 Cu1 127.2(2) . . ?
C1 N2 H2 116.9 . . ?
C2 N2 H2 116.9 . . ?
C2 N2 C1 126.1(3) . . ?
C5 N3 Cu1 126.3(3) . . ?
C9 N3 Cu1 114.4(2) . . ?
C9 N3 C5 119.3(3) . . ?
Cu1 N4A H4A 106.7 . . ?
C10 N4A Cu1 108.3(3) . . ?
C10 N4A H4A 106.7 . . ?
C11 N4A Cu1 111.1(3) . . ?
C11 N4A H4A 106.7 . . ?
C11 N4A C10 116.8(4) . . ?
Cu1 N4B H4B 106.4 . . ?
C10 N4B Cu1 110.9(7) . . ?
C10 N4B H4B 106.4 . . ?
C10 N4B C11 116.8(10) . . ?
C11 N4B Cu1 109.1(8) . . ?
C11 N4B H4B 106.4 . . ?
C12 N5 Cu1 115.1(2) . . ?
C16 N5 Cu1 126.0(2) . . ?
C16 N5 C12 118.8(3) . . ?
O3 N6 O4 114.7(4) . . ?
O3 N6 O5A 123.9(5) . . ?
O5A N6 O4 111.2(4) . . ?
O5B N6 O3 110.4(5) . . ?
O5B N6 O5A 114.2(5) . . ?
O1 C1 N1 121.9(3) . . ?
O1 C1 N2 119.3(3) . . ?
N1 C1 N2 118.7(3) . . ?
O2 C2 N2 122.4(3) . . ?
O2 C2 C3 125.7(3) . . ?
N2 C2 C3 111.9(3) . . ?
F1 C3 C2 116.4(3) . . ?
C4 C3 F1 121.2(3) . . ?
C4 C3 C2 122.4(3) . . ?
N1 C4 H4 118.7 . . ?
C3 C4 N1 122.6(3) . . ?
C3 C4 H4 118.7 . . ?
N3 C5 H5 118.9 . . ?
N3 C5 C6 122.2(4) . . ?
C6 C5 H5 118.9 . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.1(4) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 120.1 . . ?
C6 C7 C8 119.7(4) . . ?
C8 C7 H7 120.1 . . ?
C7 C8 H8 120.7 . . ?
C7 C8 C9 118.5(4) . . ?
C9 C8 H8 120.7 . . ?
N3 C9 C8 121.1(4) . . ?
N3 C9 C10 116.0(3) . . ?
C8 C9 C10 122.9(4) . . ?
N4A C10 C9 110.0(3) . . ?
N4A C10 H10A 109.7 . . ?
N4A C10 H10B 109.7 . . ?
N4B C10 C9 110.9(5) . . ?
N4B C10 H10C 109.5 . . ?
N4B C10 H10D 109.5 . . ?
C9 C10 H10A 109.7 . . ?
C9 C10 H10B 109.7 . . ?
C9 C10 H10C 109.5 . . ?
C9 C10 H10D 109.5 . . ?
H10A C10 H10B 108.2 . . ?
H10C C10 H10D 108.0 . . ?
N4A C11 H11A 109.6 . . ?
N4A C11 H11B 109.6 . . ?
N4A C11 C12 110.3(3) . . ?
N4B C11 H11C 110.0 . . ?
N4B C11 H11D 110.0 . . ?
N4B C11 C12 108.5(5) . . ?
H11A C11 H11B 108.1 . . ?
H11C C11 H11D 108.4 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C12 C11 H11C 110.0 . . ?
C12 C11 H11D 110.0 . . ?
N5 C12 C11 115.7(3) . . ?
N5 C12 C13 121.0(3) . . ?
C13 C12 C11 123.3(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 C12 119.3(3) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 121.2 . . ?
C16 C15 C14 117.5(4) . . ?
C16 C15 H15 121.2 . . ?
N5 C16 C15 122.9(3) . . ?
N5 C16 H16 118.5 . . ?
C15 C16 H16 118.5 . . ?
H1WA O1W H1WB 108.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.86 2.01 2.869(3) 173.1 2_676 yes
N4A H4A O4 0.98 2.27 3.208(9) 160.1 2_667 yes
N4A H4A O4 0.98 2.00 2.883(9) 148.2 . yes
N4B H4B O1W 0.98 1.62 2.59(2) 167.8 2_676 yes
O1W H1WA O1 0.88 1.99 2.833(4) 159.4 2_676 yes
O1W H1WB O2 0.90 1.89 2.753(4) 159.9 . yes

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 N6 O4 26.6(6) . . . . ?
Cu1 O3 N6 O5A 168.8(3) . . . . ?
Cu1 O3 N6 O5B -50.1(7) . . . . ?
Cu1 N1 C1 O1 -6.4(4) . . . . ?
Cu1 N1 C1 N2 174.0(2) . . . . ?
Cu1 N1 C4 C3 -173.8(3) . . . . ?
Cu1 N3 C5 C6 -178.7(3) . . . . ?
Cu1 N3 C9 C8 179.2(2) . . . . ?
Cu1 N3 C9 C10 -0.9(4) . . . . ?
Cu1 N4A C10 C9 -31.7(5) . . . . ?
Cu1 N4A C11 C12 24.9(5) . . . . ?
Cu1 N4B C10 C9 26.1(13) . . . . ?
Cu1 N4B C11 C12 -31.8(11) . . . . ?
Cu1 N5 C12 C11 5.4(4) . . . . ?
Cu1 N5 C12 C13 -175.8(2) . . . . ?
Cu1 N5 C16 C15 175.1(2) . . . . ?
F1 C3 C4 N1 -179.9(3) . . . . ?
O2 C2 C3 F1 1.0(6) . . . . ?
O2 C2 C3 C4 -179.0(4) . . . . ?
N2 C2 C3 F1 178.9(3) . . . . ?
N2 C2 C3 C4 -1.1(6) . . . . ?
N3 C5 C6 C7 0.1(6) . . . . ?
N3 C9 C10 N4A 22.2(5) . . . . ?
N3 C9 C10 N4B -17.0(10) . . . . ?
N4A C11 C12 N5 -20.2(5) . . . . ?
N4A C11 C12 C13 161.0(4) . . . . ?
N4B C11 C12 N5 17.9(9) . . . . ?
N4B C11 C12 C13 -160.9(8) . . . . ?
N5 C12 C13 C14 0.0(5) . . . . ?
C1 N1 C4 C3 1.4(5) . . . . ?
C1 N2 C2 O2 178.7(3) . . . . ?
C1 N2 C2 C3 0.7(5) . . . . ?
C2 N2 C1 O1 -178.9(3) . . . . ?
C2 N2 C1 N1 0.7(5) . . . . ?
C2 C3 C4 N1 0.1(7) . . . . ?
C4 N1 C1 O1 177.8(3) . . . . ?
C4 N1 C1 N2 -1.8(4) . . . . ?
C5 N3 C9 C8 0.8(5) . . . . ?
C5 N3 C9 C10 -179.2(3) . . . . ?
C5 C6 C7 C8 0.1(6) . . . . ?
C6 C7 C8 C9 0.2(6) . . . . ?
C7 C8 C9 N3 -0.6(5) . . . . ?
C7 C8 C9 C10 179.4(3) . . . . ?
C8 C9 C10 N4A -157.8(4) . . . . ?
C8 C9 C10 N4B 163.0(9) . . . . ?
C9 N3 C5 C6 -0.6(5) . . . . ?
C10 N4A C11 C12 149.9(4) . . . . ?
C10 N4B C11 C12 -158.7(10) . . . . ?
C11 N4A C10 C9 -158.0(4) . . . . ?
C11 N4B C10 C9 152.0(9) . . . . ?
C11 C12 C13 C14 178.7(3) . . . . ?
C12 N5 C16 C15 -0.4(5) . . . . ?
C12 C13 C14 C15 0.1(5) . . . . ?
C13 C14 C15 C16 -0.3(5) . . . . ?
C14 C15 C16 N5 0.5(5) . . . . ?
C16 N5 C12 C11 -178.6(3) . . . . ?
C16 N5 C12 C13 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
;
_twin_special_details            
;
Component 2 rotated by 18.7537° 
around [-0.49 -0.83 -0.27] (reciprocal) or [-0.37 -0.93 -0.01] (direct)
;
####################################################################### 
# 
# 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_Compound_II
_database_code_depnum_ccdc_archive 'CCDC 2158099'
loop_
_audit_author_name
_audit_author_address
'Muhittin Aygun'
;Dokuz Eylul University
Turkey
;
_audit_update_record             
;
2023-03-06 deposited with the CCDC.	2023-03-09 downloaded from the CCDC.
;
_audit_creation_date             2021-12-17
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C28 H18 Cu F N6 O2, C4 H2 F N2 O2, H2 O, 3[H2O]'
_chemical_formula_sum            'C32 H28 Cu F2 N8 O8'
_chemical_formula_weight         700.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.1277(13)
_cell_length_b                   19.623(3)
_cell_length_c                   24.848(3)
_cell_angle_alpha                90
_cell_angle_beta                 95.728(10)
_cell_angle_gamma                90
_cell_volume                     6369.0(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1986
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      23.9000
_cell_measurement_theta_min      3.3710
_shelx_estimated_absorpt_T_max   0.883
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.752
_exptl_absorpt_correction_T_max  0.886
_exptl_absorpt_correction_T_min  0.836
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             2856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
3 -21 -22 0.1065
-18 -6 -4 0.1190
18 0 -3 0.1134
8 -16 22 0.1004
-8 16 -22 0.1004
14 11 -22 0.1300
0 -2 35 0.0706
-1 7 -34 0.0983
-17 4 -8 0.1132
8 -25 3 0.1145
-2 -19 25 0.1085
-4 19 25 0.0950
-6 26 3 0.0794
-6 25 -7 0.0712
-9 -20 -15 0.1313
1 -7 -34 0.1021
-14 -11 22 0.1195

_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            9494
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.296
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 8.0667
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  79.00   1.00   10.18    --   20.07   0.00 150.00  110
  2  ω    -30.00  11.00   1.00   10.18    --  -22.10 -77.00-180.00   41
  3  ω   -103.00 -54.00   1.00   10.18    --  -22.10 168.00  -1.31   49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3029
_reflns_number_total             5577
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.663
_refine_diff_density_min         -0.589
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5577
_refine_ls_number_restraints     414
_refine_ls_R_factor_all          0.1655
_refine_ls_R_factor_gt           0.1103
_refine_ls_restrained_S_all      1.024
_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)+(0.0861P)²+79.0813P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2640
_refine_ls_wR_factor_ref         0.2998
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3.a Riding coordinates:
 N7(H7)
3.b Free rotating group:
 O1W(H1WA,H1WB)
3.c Aromatic/amide H refined with riding coordinates:
 N1(H2), C2(H2A), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14), C16(H16),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C25(H25), C26(H26), C28(H28),
  C29(H29), C30(H70), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.51673(8) 0.32898(6) 0.35675(5) 0.0500(4) Uani 1 1 d . . . . .
F1 F 0.3601(7) 0.2749(4) 0.5407(3) 0.106(3) Uani 1 1 d . . . . .
O1 O 0.4836(7) 0.1824(4) 0.3579(4) 0.092(3) Uani 1 1 d . . . . .
O2 O 0.4372(5) 0.3606(4) 0.4679(3) 0.0640(19) Uani 1 1 d . . . . .
N2 N 0.4604(6) 0.2715(4) 0.4120(3) 0.0529(16) Uani 1 1 d . . . . .
N1 N 0.4162(10) 0.1623(5) 0.4358(4) 0.097(3) Uani 1 1 d . . . . .
H2 H 0.410621 0.119699 0.427817 0.116 Uiso 1 1 calc R U . . .
N3 N 0.6548(6) 0.3347(4) 0.3985(3) 0.0543(18) Uani 1 1 d . . . . .
N4 N 0.5315(6) 0.4391(4) 0.3658(3) 0.0492(17) Uani 1 1 d . . . . .
N5 N 0.5750(5) 0.3256(4) 0.2818(3) 0.0484(16) Uani 1 1 d . . . . .
N6 N 0.3851(5) 0.3312(4) 0.3079(3) 0.0444(15) Uani 1 1 d . . . . .
C1 C 0.4567(9) 0.2048(6) 0.4006(5) 0.066(2) Uani 1 1 d . . . . .
C2 C 0.3844(12) 0.1835(6) 0.4825(5) 0.096(4) Uani 1 1 d . . . . .
H2A H 0.358786 0.152789 0.506335 0.115 Uiso 1 1 calc R U . . .
C3 C 0.3908(10) 0.2513(6) 0.4943(4) 0.076(3) Uani 1 1 d . . . . .
C4 C 0.4296(7) 0.2990(5) 0.4587(4) 0.0523(19) Uani 1 1 d . . . . .
C9 C 0.7160(8) 0.2845(7) 0.4149(4) 0.073(3) Uani 1 1 d . . . . .
H9 H 0.692856 0.240063 0.408986 0.087 Uiso 1 1 calc R U . . .
C10 C 0.8135(8) 0.2943(8) 0.4408(4) 0.080(3) Uani 1 1 d . . . . .
H10 H 0.854823 0.256959 0.450587 0.096 Uiso 1 1 calc R U . . .
C11 C 0.8487(8) 0.3584(8) 0.4517(4) 0.075(3) Uani 1 1 d . . . . .
H11 H 0.913698 0.364960 0.469487 0.090 Uiso 1 1 calc R U . . .
C12 C 0.7870(7) 0.4143(7) 0.4361(4) 0.067(2) Uani 1 1 d . . . . .
C13 C 0.8151(9) 0.4839(8) 0.4454(4) 0.075(3) Uani 1 1 d . . . . .
H13 H 0.880496 0.494094 0.461314 0.091 Uiso 1 1 calc R U . . .
C14 C 0.7510(11) 0.5342(8) 0.4319(5) 0.092(3) Uani 1 1 d . . . . .
H14 H 0.771033 0.578756 0.440314 0.110 Uiso 1 1 calc R U . . .
C15 C 0.6532(9) 0.5223(6) 0.4053(4) 0.068(2) Uani 1 1 d . . . . .
C16 C 0.5814(11) 0.5748(6) 0.3879(5) 0.084(3) Uani 1 1 d . . . . .
H16 H 0.596729 0.620306 0.395457 0.101 Uiso 1 1 calc R U . . .
C17 C 0.4920(10) 0.5574(6) 0.3607(5) 0.077(3) Uani 1 1 d . . . . .
H17 H 0.445224 0.591219 0.349193 0.093 Uiso 1 1 calc R U . . .
C18 C 0.4679(8) 0.4891(5) 0.3493(5) 0.062(3) Uani 1 1 d . . . . .
H18 H 0.405848 0.478469 0.329745 0.074 Uiso 1 1 calc R U . . .
C19 C 0.6232(7) 0.4545(5) 0.3933(4) 0.054(2) Uani 1 1 d . . . . .
C20 C 0.6882(7) 0.4002(6) 0.4087(4) 0.054(2) Uani 1 1 d . . . . .
C21 C 0.6735(7) 0.3232(5) 0.2668(5) 0.058(2) Uani 1 1 d . . . . .
H21 H 0.727413 0.321076 0.294054 0.070 Uiso 1 1 calc R U . . .
C22 C 0.6954(9) 0.3239(6) 0.2162(5) 0.069(3) Uani 1 1 d . . . . .
H22 H 0.763317 0.321777 0.208683 0.083 Uiso 1 1 calc R U . . .
C23 C 0.6174(8) 0.3276(5) 0.1739(5) 0.066(2) Uani 1 1 d . . . . .
H23 H 0.632943 0.327672 0.138221 0.079 Uiso 1 1 calc R U . . .
C24 C 0.5158(8) 0.3313(5) 0.1856(4) 0.056(2) Uani 1 1 d . . . . .
C25 C 0.4329(9) 0.3351(6) 0.1454(4) 0.068(3) Uani 1 1 d . . . . .
H25 H 0.444584 0.335047 0.109120 0.081 Uiso 1 1 calc R U . . .
C26 C 0.3347(9) 0.3390(6) 0.1596(4) 0.067(3) Uani 1 1 d . . . . .
H26 H 0.280529 0.343458 0.132696 0.081 Uiso 1 1 calc R U . . .
C27 C 0.3147(7) 0.3364(5) 0.2143(4) 0.049(2) Uani 1 1 d . . . . .
C28 C 0.2179(7) 0.3396(5) 0.2317(4) 0.056(2) Uani 1 1 d . . . . .
H28 H 0.160459 0.343016 0.206751 0.067 Uiso 1 1 calc R U . . .
C29 C 0.2076(7) 0.3379(5) 0.2841(4) 0.054(2) Uani 1 1 d . . . . .
H29 H 0.142382 0.339937 0.295529 0.065 Uiso 1 1 calc R U . . .
C30 C 0.2926(6) 0.3329(5) 0.3228(4) 0.047(2) Uani 1 1 d . . . . .
H70 H 0.283006 0.330912 0.359390 0.057 Uiso 1 1 calc R U . . .
C31 C 0.3989(6) 0.3326(4) 0.2543(4) 0.0424(17) Uani 1 1 d . . . . .
C32 C 0.4982(7) 0.3304(5) 0.2406(4) 0.0461(18) Uani 1 1 d . . . . .
F2 F 0.7649(6) 0.0239(4) 0.2091(3) 0.106(3) Uani 1 1 d . . . . .
O3 O 0.6397(7) 0.0217(5) 0.2886(5) 0.131(4) Uani 1 1 d . . . . .
O4 O 0.9209(12) -0.0214(6) 0.4088(4) 0.167(5) Uani 1 1 d . . . . .
N7 N 0.7814(10) -0.0015(6) 0.3547(5) 0.101(3) Uani 1 1 d . . . . .
H7 H 0.750712 -0.033985 0.369760 0.121 Uiso 1 1 d R U . . .
N8 N 0.9424(9) -0.0062(6) 0.3207(5) 0.089(3) Uani 1 1 d . . . . .
C5 C 0.8877(13) -0.0119(6) 0.3574(6) 0.086(3) Uani 1 1 d . . . . .
C6 C 0.7303(10) 0.0121(6) 0.3024(6) 0.080(3) Uani 1 1 d . . . . .
C7 C 0.8021(8) 0.0115(5) 0.2606(4) 0.061(2) Uani 1 1 d . . . . .
C8 C 0.8979(9) 0.0040(6) 0.2729(5) 0.065(3) Uani 1 1 d . . . . .
H8 H 0.939483 0.006023 0.244723 0.079 Uiso 1 1 calc R U . . .
O1W O 0.5508(7) 0.1509(6) 0.2552(4) 0.106(3) Uani 1 1 d G . . . .
H1WA H 0.599653 0.124458 0.266217 0.159 Uiso 1 1 d G U . . .
H1WB H 0.534263 0.170164 0.283728 0.159 Uiso 1 1 d G 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 N2 1.977(8) . ?
Cu1 N3 2.000(7) . ?
Cu1 N4 2.179(8) . ?
Cu1 N5 2.085(8) . ?
Cu1 N6 2.011(6) . ?
F1 C3 1.342(14) . ?
O1 C1 1.232(14) . ?
O2 C4 1.231(11) . ?
N2 C1 1.339(13) . ?
N2 C4 1.378(13) . ?
N1 H2 0.8600 . ?
N1 C1 1.357(15) . ?
N1 C2 1.338(17) . ?
N3 C9 1.310(13) . ?
N3 C20 1.374(13) . ?
N4 C18 1.326(12) . ?
N4 C19 1.357(11) . ?
N5 C21 1.381(12) . ?
N5 C32 1.365(10) . ?
N6 C30 1.305(11) . ?
N6 C31 1.362(11) . ?
C2 H2A 0.9300 . ?
C2 C3 1.364(16) . ?
C3 C4 1.417(15) . ?
C9 H9 0.9300 . ?
C9 C10 1.387(13) . ?
C10 H10 0.9300 . ?
C10 C11 1.357(18) . ?
C11 H11 0.9300 . ?
C11 C12 1.396(17) . ?
C12 C13 1.429(17) . ?
C12 C20 1.430(12) . ?
C13 H13 0.9300 . ?
C13 C14 1.319(18) . ?
C14 H14 0.9300 . ?
C14 C15 1.404(16) . ?
C15 C16 1.432(17) . ?
C15 C19 1.412(14) . ?
C16 H16 0.9300 . ?
C16 C17 1.339(17) . ?
C17 H17 0.9300 . ?
C17 C18 1.400(15) . ?
C18 H18 0.9300 . ?
C19 C20 1.394(14) . ?
C21 H21 0.9300 . ?
C21 C22 1.318(15) . ?
C22 H22 0.9300 . ?
C22 C23 1.395(15) . ?
C23 H23 0.9300 . ?
C23 C24 1.395(14) . ?
C24 C25 1.403(13) . ?
C24 C32 1.410(13) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(15) . ?
C26 H26 0.9300 . ?
C26 C27 1.411(14) . ?
C27 C28 1.384(14) . ?
C27 C31 1.414(11) . ?
C28 H28 0.9300 . ?
C28 C29 1.322(14) . ?
C29 H29 0.9300 . ?
C29 C30 1.402(11) . ?
C30 H70 0.9300 . ?
C31 C32 1.381(13) . ?
F2 C7 1.345(12) . ?
O3 C6 1.219(15) . ?
O4 C5 1.321(15) . ?
N7 H7 0.8598 . ?
N7 C5 1.406(18) . ?
N7 C6 1.428(17) . ?
N8 C5 1.221(17) . ?
N8 C8 1.287(14) . ?
C6 C7 1.470(16) . ?
C7 C8 1.273(14) . ?
C8 H8 0.9300 . ?
O1W H1WA 0.8489 . ?
O1W H1WB 0.8503 . ?

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
N2 Cu1 N3 93.1(3) . . ?
N2 Cu1 N4 122.0(3) . . ?
N2 Cu1 N5 143.0(3) . . ?
N2 Cu1 N6 94.2(3) . . ?
N3 Cu1 N4 79.9(3) . . ?
N3 Cu1 N5 94.1(3) . . ?
N3 Cu1 N6 172.7(3) . . ?
N5 Cu1 N4 95.0(3) . . ?
N6 Cu1 N4 95.9(3) . . ?
N6 Cu1 N5 80.3(3) . . ?
C1 N2 Cu1 114.8(8) . . ?
C1 N2 C4 123.7(10) . . ?
C4 N2 Cu1 121.5(7) . . ?
C1 N1 H2 118.5 . . ?
C2 N1 H2 118.5 . . ?
C2 N1 C1 123.1(11) . . ?
C9 N3 Cu1 127.9(8) . . ?
C9 N3 C20 118.2(8) . . ?
C20 N3 Cu1 113.8(6) . . ?
C18 N4 Cu1 130.9(7) . . ?
C18 N4 C19 119.4(9) . . ?
C19 N4 Cu1 109.7(6) . . ?
C21 N5 Cu1 132.7(6) . . ?
C32 N5 Cu1 110.9(6) . . ?
C32 N5 C21 116.2(9) . . ?
C30 N6 Cu1 126.7(6) . . ?
C30 N6 C31 119.7(7) . . ?
C31 N6 Cu1 113.6(6) . . ?
O1 C1 N2 121.6(12) . . ?
O1 C1 N1 120.1(11) . . ?
N2 C1 N1 118.2(12) . . ?
N1 C2 H2A 120.9 . . ?
N1 C2 C3 118.1(13) . . ?
C3 C2 H2A 120.9 . . ?
F1 C3 C2 120.2(12) . . ?
F1 C3 C4 117.7(10) . . ?
C2 C3 C4 122.0(13) . . ?
O2 C4 N2 121.0(10) . . ?
O2 C4 C3 124.1(11) . . ?
N2 C4 C3 114.8(10) . . ?
N3 C9 H9 118.4 . . ?
N3 C9 C10 123.2(12) . . ?
C10 C9 H9 118.4 . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.1(12) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.7(9) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 125.0(10) . . ?
C11 C12 C20 117.1(11) . . ?
C13 C12 C20 117.9(11) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 C12 121.8(11) . . ?
C14 C13 H13 119.1 . . ?
C13 C14 H14 119.1 . . ?
C13 C14 C15 121.7(13) . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C16 124.4(12) . . ?
C14 C15 C19 118.6(12) . . ?
C19 C15 C16 116.9(10) . . ?
C15 C16 H16 120.5 . . ?
C17 C16 C15 119.0(11) . . ?
C17 C16 H16 120.5 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 121.0(12) . . ?
C18 C17 H17 119.5 . . ?
N4 C18 C17 121.5(11) . . ?
N4 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?
N4 C19 C15 122.0(10) . . ?
N4 C19 C20 117.2(9) . . ?
C20 C19 C15 120.8(9) . . ?
N3 C20 C12 121.7(10) . . ?
N3 C20 C19 119.3(8) . . ?
C19 C20 C12 119.0(10) . . ?
N5 C21 H21 118.1 . . ?
C22 C21 N5 123.8(9) . . ?
C22 C21 H21 118.1 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.4(11) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.5(11) . . ?
C24 C23 H23 120.3 . . ?
C23 C24 C25 123.0(10) . . ?
C23 C24 C32 116.9(9) . . ?
C25 C24 C32 120.1(10) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(10) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.5 . . ?
C25 C26 C27 121.0(9) . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C31 118.2(9) . . ?
C28 C27 C26 124.4(8) . . ?
C28 C27 C31 117.3(9) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 C27 119.6(8) . . ?
C29 C28 H28 120.2 . . ?
C28 C29 H29 119.2 . . ?
C28 C29 C30 121.7(10) . . ?
C30 C29 H29 119.2 . . ?
N6 C30 C29 120.4(9) . . ?
N6 C30 H70 119.8 . . ?
C29 C30 H70 119.8 . . ?
N6 C31 C27 121.2(8) . . ?
N6 C31 C32 117.5(7) . . ?
C32 C31 C27 121.3(9) . . ?
N5 C32 C24 123.2(9) . . ?
N5 C32 C31 117.5(9) . . ?
C31 C32 C24 119.2(8) . . ?
C5 N7 H7 112.2 . . ?
C5 N7 C6 116.4(12) . . ?
C6 N7 H7 109.7 . . ?
C5 N8 C8 117.3(14) . . ?
O4 C5 N7 107.3(15) . . ?
N8 C5 O4 125.0(17) . . ?
N8 C5 N7 127.3(13) . . ?
O3 C6 N7 129.9(14) . . ?
O3 C6 C7 118.6(14) . . ?
N7 C6 C7 111.4(12) . . ?
F2 C7 C6 118.2(11) . . ?
C8 C7 F2 120.4(11) . . ?
C8 C7 C6 121.3(12) . . ?
N8 C8 H8 117.1 . . ?
C7 C8 N8 125.9(13) . . ?
C7 C8 H8 117.1 . . ?
H1WA O1W H1WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H2 O4 0.86 1.99 2.847(15) 171.2 6 yes
O1W H1WA O3 0.85 2.14 2.878(15) 144.8 . yes
O1W H1WB O1 0.85 2.03 2.849(14) 160.3 . yes

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 N2 C1 O1 -2.3(12) . . . . ?
Cu1 N2 C1 N1 -178.1(7) . . . . ?
Cu1 N2 C4 O2 -0.7(11) . . . . ?
Cu1 N2 C4 C3 179.9(7) . . . . ?
Cu1 N3 C9 C10 175.7(8) . . . . ?
Cu1 N3 C20 C12 -177.4(7) . . . . ?
Cu1 N3 C20 C19 4.5(12) . . . . ?
Cu1 N4 C18 C17 178.5(8) . . . . ?
Cu1 N4 C19 C15 -179.6(8) . . . . ?
Cu1 N4 C19 C20 1.4(11) . . . . ?
Cu1 N5 C21 C22 -177.3(8) . . . . ?
Cu1 N5 C32 C24 178.2(8) . . . . ?
Cu1 N5 C32 C31 -3.5(10) . . . . ?
Cu1 N6 C30 C29 176.7(7) . . . . ?
Cu1 N6 C31 C27 -178.0(7) . . . . ?
Cu1 N6 C31 C32 1.9(10) . . . . ?
F1 C3 C4 O2 0.2(15) . . . . ?
F1 C3 C4 N2 179.6(9) . . . . ?
N1 C2 C3 F1 -179.8(11) . . . . ?
N1 C2 C3 C4 0(2) . . . . ?
N3 C9 C10 C11 2.1(19) . . . . ?
N4 C19 C20 N3 -4.0(14) . . . . ?
N4 C19 C20 C12 177.9(8) . . . . ?
N5 C21 C22 C23 0.5(17) . . . . ?
N6 C31 C32 N5 1.2(13) . . . . ?
N6 C31 C32 C24 179.5(8) . . . . ?
C1 N2 C4 O2 178.1(8) . . . . ?
C1 N2 C4 C3 -1.4(12) . . . . ?
C1 N1 C2 C3 2(2) . . . . ?
C2 N1 C1 O1 -179.2(12) . . . . ?
C2 N1 C1 N2 -3.3(17) . . . . ?
C2 C3 C4 O2 -179.6(11) . . . . ?
C2 C3 C4 N2 -0.2(16) . . . . ?
C4 N2 C1 O1 178.9(9) . . . . ?
C4 N2 C1 N1 3.0(14) . . . . ?
C9 N3 C20 C12 0.3(15) . . . . ?
C9 N3 C20 C19 -177.8(10) . . . . ?
C9 C10 C11 C12 -1.0(18) . . . . ?
C10 C11 C12 C13 179.8(11) . . . . ?
C10 C11 C12 C20 -0.3(16) . . . . ?
C11 C12 C13 C14 -176.5(12) . . . . ?
C11 C12 C20 N3 0.7(15) . . . . ?
C11 C12 C20 C19 178.7(10) . . . . ?
C12 C13 C14 C15 -3.2(19) . . . . ?
C13 C12 C20 N3 -179.4(9) . . . . ?
C13 C12 C20 C19 -1.4(14) . . . . ?
C13 C14 C15 C16 -177.6(12) . . . . ?
C13 C14 C15 C19 0.6(18) . . . . ?
C14 C15 C16 C17 177.0(12) . . . . ?
C14 C15 C19 N4 -177.4(10) . . . . ?
C14 C15 C19 C20 1.5(16) . . . . ?
C15 C16 C17 C18 0.2(19) . . . . ?
C15 C19 C20 N3 177.0(9) . . . . ?
C15 C19 C20 C12 -1.1(15) . . . . ?
C16 C15 C19 N4 1.0(15) . . . . ?
C16 C15 C19 C20 179.9(10) . . . . ?
C16 C17 C18 N4 1.2(18) . . . . ?
C18 N4 C19 C15 0.3(15) . . . . ?
C18 N4 C19 C20 -178.6(9) . . . . ?
C19 N4 C18 C17 -1.5(15) . . . . ?
C19 C15 C16 C17 -1.3(17) . . . . ?
C20 N3 C9 C10 -1.7(17) . . . . ?
C20 C12 C13 C14 3.6(16) . . . . ?
C21 N5 C32 C24 1.6(13) . . . . ?
C21 N5 C32 C31 179.8(8) . . . . ?
C21 C22 C23 C24 0.5(17) . . . . ?
C22 C23 C24 C25 -179.9(10) . . . . ?
C22 C23 C24 C32 -0.5(15) . . . . ?
C23 C24 C25 C26 -179.7(11) . . . . ?
C23 C24 C32 N5 -0.6(15) . . . . ?
C23 C24 C32 C31 -178.8(9) . . . . ?
C24 C25 C26 C27 -2.7(17) . . . . ?
C25 C24 C32 N5 178.8(9) . . . . ?
C25 C24 C32 C31 0.6(15) . . . . ?
C25 C26 C27 C28 -179.6(10) . . . . ?
C25 C26 C27 C31 2.7(16) . . . . ?
C26 C27 C28 C29 -178.9(10) . . . . ?
C26 C27 C31 N6 178.8(9) . . . . ?
C26 C27 C31 C32 -1.1(14) . . . . ?
C27 C28 C29 C30 0.1(15) . . . . ?
C27 C31 C32 N5 -178.9(8) . . . . ?
C27 C31 C32 C24 -0.6(14) . . . . ?
C28 C27 C31 N6 1.0(13) . . . . ?
C28 C27 C31 C32 -178.9(9) . . . . ?
C28 C29 C30 N6 1.2(15) . . . . ?
C30 N6 C31 C27 0.3(13) . . . . ?
C30 N6 C31 C32 -179.8(8) . . . . ?
C31 N6 C30 C29 -1.4(13) . . . . ?
C31 C27 C28 C29 -1.2(14) . . . . ?
C32 N5 C21 C22 -1.6(15) . . . . ?
C32 C24 C25 C26 1.0(16) . . . . ?
F2 C7 C8 N8 178.1(11) . . . . ?
O3 C6 C7 F2 2.1(17) . . . . ?
O3 C6 C7 C8 177.6(12) . . . . ?
N7 C6 C7 F2 -179.7(10) . . . . ?
N7 C6 C7 C8 -4.2(16) . . . . ?
C5 N7 C6 O3 178.6(13) . . . . ?
C5 N7 C6 C7 0.6(16) . . . . ?
C5 N8 C8 C7 3(2) . . . . ?
C6 N7 C5 O4 178.0(10) . . . . ?
C6 N7 C5 N8 5(2) . . . . ?
C6 C7 C8 N8 2.6(19) . . . . ?
C8 N8 C5 O4 -178.8(12) . . . . ?
C8 N8 C5 N7 -7(2) . . . . ?

_smtbx_masks_special_details     
;
A solvent mask was calculated and 246 electrons were 
found in a volume of 762Å³ in 1 void per unit cell. 
This is consistent with the presence of 
3[H2O] per Asymmetric Unit 
which account for 240 electrons 
per unit cell.
;
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.231 0.000 0.500 380.8 122.8 '12 H2O'
2 -0.109 0.500 1.000 380.8 122.8 '12 H2O'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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
;
# start Validation Reply Form
_vrf_PLAT341_Compound_II         
;
 PROBLEM: Low Bond Precision on  C-C Bonds ......... 0.01575 Ang.
RESPONSE: 
The anisotropic displacement parameters of some atoms 
are high due to poor crystal quality. 
This may be a consequence to an increase in 
the uncertainty of the average C-C bond lengths.
;
_vrf_PLAT430_Compound_II         
;
 PROBLEM: Short Inter D...A Contact  O3       ..N8       .       2.80 Ang.  
                                                -1/2+x,-y,z  =      6_555 Check
RESPONSE: There are very large voids in the crystal structure. These
 spaces are filled with barbiturate ligands and water molecules. 
Short-interactions between barbiturate molecules are not abnormal.
;

