# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
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data_20191030-czf-zhq-p-p-cuclo4-meoh-chcnaaayong_pl
_database_code_depnum_ccdc_archive 'CCDC 2222143'
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H15 Cu N2 O3, Cl O4'
_chemical_formula_sum            'C21 H15 Cl Cu N2 O7'
_chemical_formula_weight         506.34
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.2985(5)
_cell_length_b                   10.3543(7)
_cell_length_c                   11.9616(7)
_cell_angle_alpha                112.775(6)
_cell_angle_beta                 107.363(5)
_cell_angle_gamma                93.359(5)
_cell_volume                     993.44(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2571
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.1010
_cell_measurement_theta_min      3.8040
_shelx_estimated_absorpt_T_max   0.861
_shelx_estimated_absorpt_T_min   0.723
_exptl_absorpt_coefficient_mu    1.284
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.693
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             514
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0417
_diffrn_reflns_av_unetI/netI     0.0589
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12106
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         3.416
_diffrn_ambient_temperature      298.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'four-circle diffractometer'
_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                2972
_reflns_number_total             4043
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.742
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0527
_refine_ls_restrained_S_all      1.049
_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)+(0.0605P)²+1.0517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1248
_refine_ls_wR_factor_ref         0.1450
_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.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C13(H13), C18(H18), C10(H10), C12(H12), C1(H1), C4(H4), C7(H7),
 C9(H9), C3(H3), C2(H2), C8(H8)
2.b Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 1.10896(5) 0.37900(5) 0.04192(5) 0.03606(19) Uani 1 1 d . . . . .
O1 O 1.0862(3) 0.4437(3) -0.0897(3) 0.0387(7) Uani 1 1 d . . . . .
O2 O 1.2892(3) 0.5253(3) 0.1568(3) 0.0384(7) Uani 1 1 d . . . . .
O3 O 1.7083(3) 0.7892(4) 0.0541(3) 0.0555(9) Uani 1 1 d . . . . .
N2 N 1.1121(4) 0.3076(4) 0.1741(3) 0.0348(8) Uani 1 1 d . . . . .
N1 N 0.9318(3) 0.2167(4) -0.0654(3) 0.0333(8) Uani 1 1 d . . . . .
C20 C 1.3389(4) 0.5881(4) -0.0019(4) 0.0310(8) Uani 1 1 d . . . . .
C11 C 1.1975(4) 0.5148(4) -0.1015(4) 0.0319(9) Uani 1 1 d . . . . .
C19 C 1.3746(4) 0.5952(4) 0.1265(4) 0.0330(9) Uani 1 1 d . . . . .
C14 C 1.4224(5) 0.6636(5) -0.1445(5) 0.0433(11) Uani 1 1 d . . . . .
H14 H 1.496976 0.711389 -0.159718 0.052 Uiso 1 1 calc R U . . .
C16 C 1.6040(5) 0.7390(4) 0.0787(5) 0.0408(10) Uani 1 1 d . . . . .
C6 C 0.9938(4) 0.2004(4) 0.1370(4) 0.0358(9) Uani 1 1 d . . . . .
C15 C 1.4514(4) 0.6635(4) -0.0253(4) 0.0363(9) Uani 1 1 d . . . . .
C13 C 1.2810(5) 0.5921(5) -0.2431(5) 0.0445(11) Uani 1 1 d . . . . .
H13 H 1.261782 0.593801 -0.323415 0.053 Uiso 1 1 calc R U . . .
C18 C 1.5159(4) 0.6847(5) 0.2294(4) 0.0389(10) Uani 1 1 d . . . . .
H18 H 1.530015 0.696158 0.313262 0.047 Uiso 1 1 calc R U . . .
C10 C 1.2105(5) 0.3629(5) 0.2960(4) 0.0479(11) Uani 1 1 d . . . . .
H10 H 1.292726 0.436107 0.321650 0.057 Uiso 1 1 calc R U . . .
C5 C 0.8924(4) 0.1483(4) 0.0005(4) 0.0352(9) Uani 1 1 d . . . . .
C17 C 1.6269(4) 0.7518(5) 0.2093(4) 0.0400(10) Uani 1 1 d . . . . .
C12 C 1.1703(5) 0.5194(5) -0.2229(4) 0.0394(10) Uani 1 1 d . . . . .
H12 H 1.076508 0.472879 -0.289398 0.047 Uiso 1 1 calc R U . . .
C1 C 0.8479(5) 0.1758(5) -0.1896(4) 0.0407(10) Uani 1 1 d . . . . .
H1 H 0.876232 0.222491 -0.234705 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7665(5) 0.0353(5) -0.0606(5) 0.0473(11) Uani 1 1 d . . . . .
H4 H 0.741376 -0.013248 -0.015778 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9692(5) 0.1493(5) 0.2215(5) 0.0495(12) Uani 1 1 d . . . . .
H7 H 0.886124 0.076288 0.194117 0.059 Uiso 1 1 calc R U . . .
C9 C 1.1941(6) 0.3154(6) 0.3843(5) 0.0594(13) Uani 1 1 d . . . . .
H9 H 1.265315 0.354387 0.468031 0.071 Uiso 1 1 calc R U . . .
C3 C 0.6804(5) -0.0032(5) -0.1874(5) 0.0548(13) Uani 1 1 d . . . . .
H3 H 0.594511 -0.076808 -0.228979 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7212(5) 0.0671(5) -0.2530(5) 0.0499(11) Uani 1 1 d . . . . .
H2 H 0.663687 0.041491 -0.339390 0.060 Uiso 1 1 calc R U . . .
C8 C 1.0700(6) 0.2084(6) 0.3475(5) 0.0625(14) Uani 1 1 d . . . . .
H8 H 1.054933 0.177002 0.407010 0.075 Uiso 1 1 calc R U . . .
C21 C 1.7764(5) 0.8368(5) 0.3145(5) 0.0546(13) Uani 1 1 d . . . . .
H21A H 1.773064 0.843102 0.395869 0.082 Uiso 1 1 calc R U . . .
H21B H 1.793264 0.931084 0.318516 0.082 Uiso 1 1 calc R U . . .
H21C H 1.858660 0.790600 0.296475 0.082 Uiso 1 1 calc R U . . .
Cl1 Cl 0.68825(16) 0.22908(15) 0.46909(13) 0.0638(4) Uani 1 1 d . . . . .
O4 O 0.6899(5) 0.1569(4) 0.3421(4) 0.0731(11) Uani 1 1 d . . . . .
O6 O 0.6055(7) 0.1359(7) 0.4966(5) 0.140(2) Uani 1 1 d . . . . .
O7 O 0.5939(7) 0.3350(6) 0.4668(6) 0.131(2) Uani 1 1 d . . . . .
O5 O 0.8279(6) 0.2917(9) 0.5567(6) 0.179(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.899(3) . ?
Cu1 O2 1.925(3) . ?
Cu1 N2 1.982(3) . ?
Cu1 N1 1.982(3) . ?
O1 C11 1.308(4) . ?
O2 C19 1.262(4) . ?
O3 C16 1.236(5) . ?
N2 C6 1.350(5) . ?
N2 C10 1.337(5) . ?
N1 C5 1.353(5) . ?
N1 C1 1.334(5) . ?
C20 C11 1.404(5) . ?
C20 C19 1.443(5) . ?
C20 C15 1.425(5) . ?
C11 C12 1.419(5) . ?
C19 C18 1.452(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(6) . ?
C14 C13 1.397(6) . ?
C16 C15 1.496(6) . ?
C16 C17 1.463(6) . ?
C6 C5 1.478(6) . ?
C6 C7 1.376(6) . ?
C13 H13 0.9300 . ?
C13 C12 1.373(6) . ?
C18 H18 0.9300 . ?
C18 C17 1.341(5) . ?
C10 H10 0.9300 . ?
C10 C9 1.368(6) . ?
C5 C4 1.393(6) . ?
C17 C21 1.499(6) . ?
C12 H12 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.371(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.368(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.386(7) . ?
C3 H3 0.9300 . ?
C3 C2 1.370(6) . ?
C2 H2 0.9300 . ?
C8 H8 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
Cl1 O4 1.415(4) . ?
Cl1 O6 1.393(5) . ?
Cl1 O7 1.448(5) . ?
Cl1 O5 1.329(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 91.72(11) . . ?
O1 Cu1 N2 174.82(12) . . ?
O1 Cu1 N1 93.94(12) . . ?
O2 Cu1 N2 92.47(12) . . ?
O2 Cu1 N1 173.85(12) . . ?
N2 Cu1 N1 82.01(13) . . ?
C11 O1 Cu1 125.1(2) . . ?
C19 O2 Cu1 127.2(3) . . ?
C6 N2 Cu1 114.6(3) . . ?
C10 N2 Cu1 126.3(3) . . ?
C10 N2 C6 118.8(4) . . ?
C5 N1 Cu1 113.9(3) . . ?
C1 N1 Cu1 126.7(3) . . ?
C1 N1 C5 119.4(3) . . ?
C11 C20 C19 122.7(3) . . ?
C11 C20 C15 119.6(4) . . ?
C15 C20 C19 117.6(4) . . ?
O1 C11 C20 124.4(4) . . ?
O1 C11 C12 116.9(4) . . ?
C20 C11 C12 118.6(3) . . ?
O2 C19 C20 123.5(4) . . ?
O2 C19 C18 116.1(4) . . ?
C20 C19 C18 120.4(3) . . ?
C15 C14 H14 119.9 . . ?
C15 C14 C13 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
O3 C16 C15 120.3(4) . . ?
O3 C16 C17 121.0(4) . . ?
C17 C16 C15 118.7(3) . . ?
N2 C6 C5 113.9(3) . . ?
N2 C6 C7 122.1(4) . . ?
C7 C6 C5 124.0(4) . . ?
C20 C15 C16 120.2(4) . . ?
C14 C15 C20 120.3(4) . . ?
C14 C15 C16 119.5(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 C14 120.7(4) . . ?
C12 C13 H13 119.6 . . ?
C19 C18 H18 118.4 . . ?
C17 C18 C19 123.2(4) . . ?
C17 C18 H18 118.4 . . ?
N2 C10 H10 119.0 . . ?
N2 C10 C9 122.1(4) . . ?
C9 C10 H10 119.0 . . ?
N1 C5 C6 115.1(3) . . ?
N1 C5 C4 120.6(4) . . ?
C4 C5 C6 124.3(4) . . ?
C16 C17 C21 118.0(4) . . ?
C18 C17 C16 119.1(4) . . ?
C18 C17 C21 122.9(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.6(4) . . ?
C13 C12 H12 119.7 . . ?
N1 C1 H1 119.0 . . ?
N1 C1 C2 122.0(4) . . ?
C2 C1 H1 119.0 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 119.1(4) . . ?
C3 C4 H4 120.5 . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.8(4) . . ?
C8 C7 H7 120.6 . . ?
C10 C9 H9 120.4 . . ?
C10 C9 C8 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(4) . . ?
C2 C3 H3 120.1 . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C7 C8 C9 119.0(4) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O4 Cl1 O7 106.8(3) . . ?
O6 Cl1 O4 109.1(3) . . ?
O6 Cl1 O7 103.3(4) . . ?
O5 Cl1 O4 112.9(3) . . ?
O5 Cl1 O6 114.1(5) . . ?
O5 Cl1 O7 110.0(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C11 C20 -18.6(5) . . . . ?
Cu1 O1 C11 C12 162.8(3) . . . . ?
Cu1 O2 C19 C20 8.0(5) . . . . ?
Cu1 O2 C19 C18 -171.3(3) . . . . ?
Cu1 N2 C6 C5 5.3(4) . . . . ?
Cu1 N2 C6 C7 -172.7(3) . . . . ?
Cu1 N2 C10 C9 173.1(4) . . . . ?
Cu1 N1 C5 C6 -3.7(4) . . . . ?
Cu1 N1 C5 C4 177.6(3) . . . . ?
Cu1 N1 C1 C2 -175.8(3) . . . . ?
O1 C11 C12 C13 179.8(4) . . . . ?
O2 Cu1 O1 C11 24.7(3) . . . . ?
O2 C19 C18 C17 171.7(4) . . . . ?
O3 C16 C15 C20 171.0(4) . . . . ?
O3 C16 C15 C14 -7.0(6) . . . . ?
O3 C16 C17 C18 -174.0(4) . . . . ?
O3 C16 C17 C21 4.4(6) . . . . ?
N2 C6 C5 N1 -1.0(5) . . . . ?
N2 C6 C5 C4 177.6(4) . . . . ?
N2 C6 C7 C8 -0.9(7) . . . . ?
N2 C10 C9 C8 -1.3(8) . . . . ?
N1 Cu1 O1 C11 -152.9(3) . . . . ?
N1 C5 C4 C3 -1.8(6) . . . . ?
N1 C1 C2 C3 -0.9(7) . . . . ?
C20 C11 C12 C13 1.1(6) . . . . ?
C20 C19 C18 C17 -7.6(6) . . . . ?
C11 C20 C19 O2 7.2(6) . . . . ?
C11 C20 C19 C18 -173.5(4) . . . . ?
C11 C20 C15 C14 -0.5(6) . . . . ?
C11 C20 C15 C16 -178.5(4) . . . . ?
C19 C20 C11 O1 -1.6(6) . . . . ?
C19 C20 C11 C12 177.1(4) . . . . ?
C19 C20 C15 C14 -178.4(4) . . . . ?
C19 C20 C15 C16 3.7(6) . . . . ?
C19 C18 C17 C16 2.2(6) . . . . ?
C19 C18 C17 C21 -176.2(4) . . . . ?
C14 C13 C12 C11 -0.4(7) . . . . ?
C6 N2 C10 C9 -0.7(7) . . . . ?
C6 C5 C4 C3 179.7(4) . . . . ?
C6 C7 C8 C9 -1.1(8) . . . . ?
C15 C20 C11 O1 -179.3(4) . . . . ?
C15 C20 C11 C12 -0.7(6) . . . . ?
C15 C20 C19 O2 -175.0(4) . . . . ?
C15 C20 C19 C18 4.3(5) . . . . ?
C15 C14 C13 C12 -0.8(7) . . . . ?
C15 C16 C17 C18 5.9(6) . . . . ?
C15 C16 C17 C21 -175.7(4) . . . . ?
C13 C14 C15 C20 1.3(6) . . . . ?
C13 C14 C15 C16 179.2(4) . . . . ?
C10 N2 C6 C5 179.8(4) . . . . ?
C10 N2 C6 C7 1.8(6) . . . . ?
C10 C9 C8 C7 2.2(8) . . . . ?
C5 N1 C1 C2 0.8(6) . . . . ?
C5 C6 C7 C8 -178.6(4) . . . . ?
C5 C4 C3 C2 1.6(7) . . . . ?
C17 C16 C15 C20 -8.9(6) . . . . ?
C17 C16 C15 C14 173.1(4) . . . . ?
C1 N1 C5 C6 179.2(3) . . . . ?
C1 N1 C5 C4 0.6(6) . . . . ?
C4 C3 C2 C1 -0.3(7) . . . . ?
C7 C6 C5 N1 176.9(4) . . . . ?
C7 C6 C5 C4 -4.5(7) . . . . ?

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

data_20200707-czf-zhq-p-cf3-cuclo4-etoh-bingaaayong
_database_code_depnum_ccdc_archive 'CCDC 2222145'
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_audit_creation_date             2022-10-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H13 Cu F6 N2 O3, Cl O4'
_chemical_formula_sum            'C23 H13 Cl Cu F6 N2 O7'
_chemical_formula_weight         642.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.5260(4)
_cell_length_b                   16.5988(5)
_cell_length_c                   15.9965(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.658(4)
_cell_angle_gamma                90
_cell_volume                     2435.50(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3192
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.8210
_cell_measurement_theta_min      3.8940
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.755
_exptl_absorpt_coefficient_mu    1.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1284
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            16165
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.869
_diffrn_reflns_theta_min         3.310
_diffrn_ambient_temperature      298.00
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -55.00  43.00   1.00   50.00    --   17.77 -38.00 -60.00   98
  2  ω    -55.00  62.00   1.00   50.00    --   17.77 -19.00   0.00  117
  3  ω    -96.00 -34.00   1.00   50.00    --  -19.57 178.00  60.00   62
  4  ω    -88.00 -38.00   1.00   50.00    --  -19.57 -57.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, 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                3677
_reflns_number_total             5645
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.473
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     382
_refine_ls_number_reflns         5645
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0599
_refine_ls_restrained_S_all      1.081
_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)+(0.0427P)²+5.3129P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1306
_refine_ls_wR_factor_ref         0.1521
_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. Uiso/Uaniso restraints and constraints
Uanis(F3A) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1A) \\sim Ueq, Uanis(F1)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F6) \\sim Ueq, Uanis(F6A) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F5A)
\\sim Ueq, Uanis(F4) \\sim Ueq, Uanis(F4A) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
Uanis(F1) = Uanis(F1A)
Uanis(F2) = Uanis(F2A)
Uanis(F3) = Uanis(F3A)
Uanis(F6) = Uanis(F6A)
Uanis(F5) = Uanis(F5A)
Uanis(F4) = Uanis(F4A)
3. Others
 Sof(F1A)=Sof(F3A)=Sof(F2A)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
 Sof(F4A)=Sof(F6A)=Sof(F5A)=1-FVAR(2)
 Sof(F5)=Sof(F4)=Sof(F6)=FVAR(2)
4.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C7(H7), C1(H1), C20(H20), C14(H14), C10(H10), C15(H15),
 C9(H9), C16(H16)
4.b Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.18188(6) 0.03125(3) 0.50258(3) 0.03710(17) Uani 1 1 d . . . . .
Cl1 Cl 0.30792(13) 0.17287(7) 0.37776(8) 0.0484(3) Uani 1 1 d . . . . .
O2 O 0.2651(3) -0.07073(18) 0.48606(19) 0.0445(8) Uani 1 1 d . . . . .
O1 O 0.0197(3) 0.01608(18) 0.40596(19) 0.0422(7) Uani 1 1 d . . . . .
C13 C 0.0178(5) -0.0311(3) 0.3409(3) 0.0389(10) Uani 1 1 d . . . . .
N1 N 0.1169(4) 0.1386(2) 0.5308(2) 0.0318(7) Uani 1 1 d . . . . .
C5 C 0.1998(4) 0.1719(2) 0.6047(3) 0.0316(9) Uani 1 1 d . . . . .
N2 N 0.3306(4) 0.0494(2) 0.6148(2) 0.0364(8) Uani 1 1 d . . . . .
C6 C 0.3166(4) 0.1193(2) 0.6549(3) 0.0322(9) Uani 1 1 d . . . . .
C4 C 0.1739(5) 0.2485(3) 0.6294(3) 0.0385(10) Uani 1 1 d . . . . .
H4 H 0.231138 0.270658 0.680763 0.046 Uiso 1 1 calc R U . . .
C2 C -0.0251(5) 0.2576(3) 0.5011(3) 0.0397(10) Uani 1 1 d . . . . .
H2 H -0.102878 0.285688 0.465271 0.048 Uiso 1 1 calc R U . . .
C22 C 0.1171(5) -0.0961(3) 0.3429(3) 0.0386(10) Uani 1 1 d . . . . .
C7 C 0.4028(5) 0.1358(3) 0.7371(3) 0.0388(10) Uani 1 1 d . . . . .
H7 H 0.392402 0.184031 0.764378 0.047 Uiso 1 1 calc R U . . .
C1 C 0.0071(5) 0.1804(3) 0.4803(3) 0.0365(10) Uani 1 1 d . . . . .
H1 H -0.049483 0.156910 0.429605 0.044 Uiso 1 1 calc R U . . .
C19 C 0.3121(6) -0.2328(3) 0.3519(3) 0.0520(12) Uani 1 1 d . . . . .
C3 C 0.0601(5) 0.2923(3) 0.5759(3) 0.0422(11) Uani 1 1 d . . . . .
C20 C 0.3272(5) -0.1827(3) 0.4185(3) 0.0493(12) Uani 1 1 d . . . . .
H20 H 0.401502 -0.192823 0.468568 0.059 Uiso 1 1 calc R U . . .
F2 F 0.116(2) 0.4075(16) 0.6656(14) 0.076(3) Uani 0.445(7) 1 d . U P A 1
C21 C 0.2345(5) -0.1127(3) 0.4178(3) 0.0406(10) Uani 1 1 d . . . . .
C14 C -0.0926(5) -0.0189(3) 0.2629(3) 0.0467(12) Uani 1 1 d . . . . .
H14 H -0.156030 0.024439 0.258836 0.056 Uiso 1 1 calc R U . . .
C10 C 0.4321(5) -0.0037(3) 0.6541(3) 0.0483(12) Uani 1 1 d . . . . .
H10 H 0.443035 -0.050802 0.625001 0.058 Uiso 1 1 calc R U . . .
O4 O 0.4028(5) 0.1792(2) 0.3226(3) 0.0751(12) Uani 1 1 d . . . . .
O3 O 0.1835(5) -0.2597(3) 0.2077(3) 0.0865(14) Uani 1 1 d . . . . .
C18 C 0.1954(6) -0.2166(3) 0.2711(3) 0.0560(13) Uani 1 1 d . . . . .
C15 C -0.1084(6) -0.0691(4) 0.1934(3) 0.0541(13) Uani 1 1 d . . . . .
H15 H -0.182361 -0.059548 0.143035 0.065 Uiso 1 1 calc R U . . .
C9 C 0.5218(6) 0.0092(3) 0.7368(3) 0.0529(13) Uani 1 1 d . . . . .
H9 H 0.591469 -0.028615 0.763570 0.063 Uiso 1 1 calc R U . . .
C17 C 0.0974(5) -0.1476(3) 0.2697(3) 0.0452(11) Uani 1 1 d . . . . .
F5 F 0.7327(5) 0.0743(4) 0.8800(3) 0.0823(18) Uani 0.705(6) 1 d . U P B 1
F4 F 0.5946(8) 0.1674(4) 0.8983(4) 0.093(2) Uani 0.705(6) 1 d . U P B 1
C11 C 0.0293(8) 0.3759(3) 0.5993(4) 0.0709(18) Uani 1 1 d . . . . .
C12 C 0.5931(7) 0.0920(4) 0.8697(4) 0.0641(16) Uani 1 1 d . . . . .
C8 C 0.5048(5) 0.0796(3) 0.7782(3) 0.0447(11) Uani 1 1 d . . . . .
O5 O 0.1609(5) 0.1781(3) 0.3286(3) 0.0919(15) Uani 1 1 d . . . . .
C16 C -0.0156(6) -0.1340(4) 0.1969(3) 0.0582(14) Uani 1 1 d . . . . .
H16 H -0.029900 -0.168624 0.149680 0.070 Uiso 1 1 calc R U . . .
C23 C 0.4078(7) -0.3041(3) 0.3529(4) 0.0744(18) Uani 1 1 d . . . . .
H23A H 0.489267 -0.302029 0.403640 0.112 Uiso 1 1 calc R U . . .
H23B H 0.442431 -0.303636 0.301878 0.112 Uiso 1 1 calc R U . . .
H23C H 0.353254 -0.352553 0.353975 0.112 Uiso 1 1 calc R U . . .
F6 F 0.5486(9) 0.0466(5) 0.9229(4) 0.114(2) Uani 0.705(6) 1 d . U P B 1
O6 O 0.3328(5) 0.0971(2) 0.4208(3) 0.0779(13) Uani 1 1 d . . . . .
O7 O 0.3343(6) 0.2343(3) 0.4407(3) 0.1038(17) Uani 1 1 d . . . . .
F1 F 0.0490(15) 0.4252(7) 0.5267(8) 0.099(3) Uani 0.445(7) 1 d . U P A 1
F3 F -0.1027(13) 0.3898(7) 0.5927(10) 0.097(2) Uani 0.445(7) 1 d . U P A 1
F1A F -0.0412(13) 0.4187(5) 0.5374(6) 0.099(3) Uani 0.555(7) 1 d . U P A 2
F3A F -0.0644(9) 0.3705(5) 0.6562(7) 0.097(2) Uani 0.555(7) 1 d . U P A 2
F2A F 0.1460(18) 0.4139(13) 0.6459(11) 0.076(3) Uani 0.555(7) 1 d . U P A 2
F4A F 0.5009(16) 0.0997(11) 0.9234(10) 0.093(2) Uani 0.295(6) 1 d . U P B 2
F6A F 0.666(2) 0.0283(12) 0.9061(9) 0.114(2) Uani 0.295(6) 1 d . U P B 2
F5A F 0.6521(15) 0.1613(13) 0.8800(10) 0.0823(18) Uani 0.295(6) 1 d . U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.918(3) . ?
Cu1 O1 1.884(3) . ?
Cu1 N1 1.978(3) . ?
Cu1 N2 1.986(4) . ?
Cl1 O4 1.428(4) . ?
Cl1 O5 1.412(4) . ?
Cl1 O6 1.422(4) . ?
Cl1 O7 1.408(5) . ?
O2 C21 1.261(5) . ?
O1 C13 1.298(5) . ?
C13 C22 1.429(6) . ?
C13 C14 1.413(6) . ?
N1 C5 1.350(5) . ?
N1 C1 1.331(5) . ?
C5 C6 1.472(6) . ?
C5 C4 1.374(6) . ?
N2 C6 1.349(5) . ?
N2 C10 1.334(5) . ?
C6 C7 1.376(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.391(6) . ?
C2 H2 0.9300 . ?
C2 C1 1.378(6) . ?
C2 C3 1.378(6) . ?
C22 C21 1.428(6) . ?
C22 C17 1.420(6) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(6) . ?
C1 H1 0.9300 . ?
C19 C20 1.329(6) . ?
C19 C18 1.485(7) . ?
C19 C23 1.491(7) . ?
C3 C11 1.487(7) . ?
C20 H20 0.9300 . ?
C20 C21 1.457(6) . ?
F2 C11 1.27(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.365(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.385(6) . ?
O3 C18 1.221(6) . ?
C18 C17 1.474(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(7) . ?
C9 H9 0.9300 . ?
C9 C8 1.374(6) . ?
C17 C16 1.374(7) . ?
F5 C12 1.328(7) . ?
F4 C12 1.331(9) . ?
C11 F1 1.474(15) . ?
C11 F3 1.255(12) . ?
C11 F1A 1.256(10) . ?
C11 F3A 1.440(11) . ?
C11 F2A 1.320(19) . ?
C12 C8 1.492(7) . ?
C12 F6 1.292(9) . ?
C12 F4A 1.390(18) . ?
C12 F6A 1.313(19) . ?
C12 F5A 1.271(19) . ?
C16 H16 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N1 173.28(13) . . ?
O2 Cu1 N2 92.18(13) . . ?
O1 Cu1 O2 92.69(13) . . ?
O1 Cu1 N1 94.01(13) . . ?
O1 Cu1 N2 171.22(14) . . ?
N1 Cu1 N2 81.23(14) . . ?
O5 Cl1 O4 110.4(3) . . ?
O5 Cl1 O6 109.6(3) . . ?
O6 Cl1 O4 108.3(2) . . ?
O7 Cl1 O4 111.6(3) . . ?
O7 Cl1 O5 108.2(3) . . ?
O7 Cl1 O6 108.7(3) . . ?
C21 O2 Cu1 126.8(3) . . ?
C13 O1 Cu1 124.7(3) . . ?
O1 C13 C22 124.9(4) . . ?
O1 C13 C14 117.8(4) . . ?
C14 C13 C22 117.3(4) . . ?
C5 N1 Cu1 115.1(3) . . ?
C1 N1 Cu1 125.0(3) . . ?
C1 N1 C5 119.7(4) . . ?
N1 C5 C6 114.4(3) . . ?
N1 C5 C4 121.5(4) . . ?
C4 C5 C6 124.1(4) . . ?
C6 N2 Cu1 115.0(3) . . ?
C10 N2 Cu1 125.1(3) . . ?
C10 N2 C6 119.7(4) . . ?
N2 C6 C5 114.0(4) . . ?
N2 C6 C7 121.1(4) . . ?
C7 C6 C5 124.9(4) . . ?
C5 C4 H4 120.8 . . ?
C5 C4 C3 118.4(4) . . ?
C3 C4 H4 120.8 . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C3 C2 C1 118.7(4) . . ?
C21 C22 C13 121.9(4) . . ?
C17 C22 C13 119.8(4) . . ?
C17 C22 C21 118.3(4) . . ?
C6 C7 H7 120.6 . . ?
C6 C7 C8 118.9(4) . . ?
C8 C7 H7 120.6 . . ?
N1 C1 C2 121.9(4) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C20 C19 C18 118.6(5) . . ?
C20 C19 C23 123.7(5) . . ?
C18 C19 C23 117.7(4) . . ?
C4 C3 C11 120.4(4) . . ?
C2 C3 C4 119.7(4) . . ?
C2 C3 C11 119.9(4) . . ?
C19 C20 H20 118.0 . . ?
C19 C20 C21 124.0(5) . . ?
C21 C20 H20 118.0 . . ?
O2 C21 C22 124.4(4) . . ?
O2 C21 C20 115.8(4) . . ?
C22 C21 C20 119.7(4) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 C13 121.6(5) . . ?
C15 C14 H14 119.2 . . ?
N2 C10 H10 119.0 . . ?
N2 C10 C9 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
O3 C18 C19 119.8(5) . . ?
O3 C18 C17 121.8(5) . . ?
C17 C18 C19 118.4(4) . . ?
C14 C15 H15 119.6 . . ?
C14 C15 C16 120.9(5) . . ?
C16 C15 H15 119.6 . . ?
C10 C9 H9 121.0 . . ?
C8 C9 C10 118.0(4) . . ?
C8 C9 H9 121.0 . . ?
C22 C17 C18 120.9(4) . . ?
C16 C17 C22 119.9(5) . . ?
C16 C17 C18 119.2(4) . . ?
F2 C11 C3 117.9(13) . . ?
F2 C11 F1 103.6(12) . . ?
F1 C11 C3 104.1(7) . . ?
F3 C11 C3 114.3(7) . . ?
F3 C11 F2 114.0(12) . . ?
F3 C11 F1 99.8(8) . . ?
F1A C11 C3 115.5(6) . . ?
F1A C11 F3A 104.1(7) . . ?
F1A C11 F2A 111.3(11) . . ?
F3A C11 C3 107.4(6) . . ?
F2A C11 C3 113.2(10) . . ?
F2A C11 F3A 104.1(8) . . ?
F5 C12 F4 104.4(6) . . ?
F5 C12 C8 111.9(5) . . ?
F4 C12 C8 114.7(5) . . ?
F6 C12 F5 106.6(6) . . ?
F6 C12 F4 107.2(7) . . ?
F6 C12 C8 111.5(6) . . ?
F4A C12 C8 109.6(7) . . ?
F6A C12 C8 114.6(8) . . ?
F6A C12 F4A 98.4(11) . . ?
F5A C12 C8 111.4(9) . . ?
F5A C12 F4A 99.6(10) . . ?
F5A C12 F6A 120.6(11) . . ?
C7 C8 C12 120.9(4) . . ?
C9 C8 C7 120.3(4) . . ?
C9 C8 C12 118.8(4) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.5(5) . . ?
C17 C16 H16 119.8 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C21 C22 -8.4(6) . . . . ?
Cu1 O2 C21 C20 172.1(3) . . . . ?
Cu1 O1 C13 C22 20.1(6) . . . . ?
Cu1 O1 C13 C14 -161.5(3) . . . . ?
Cu1 N1 C5 C6 -4.9(4) . . . . ?
Cu1 N1 C5 C4 175.4(3) . . . . ?
Cu1 N1 C1 C2 -174.9(3) . . . . ?
Cu1 N2 C6 C5 -4.3(5) . . . . ?
Cu1 N2 C6 C7 173.3(3) . . . . ?
Cu1 N2 C10 C9 -172.5(4) . . . . ?
O2 Cu1 O1 C13 -23.6(3) . . . . ?
O1 C13 C22 C21 -2.9(7) . . . . ?
O1 C13 C22 C17 175.2(4) . . . . ?
O1 C13 C14 C15 -175.6(4) . . . . ?
C13 C22 C21 O2 -3.3(7) . . . . ?
C13 C22 C21 C20 176.2(4) . . . . ?
C13 C22 C17 C18 -178.0(4) . . . . ?
C13 C22 C17 C16 1.0(7) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
N1 Cu1 O1 C13 155.9(3) . . . . ?
N1 C5 C6 N2 6.1(5) . . . . ?
N1 C5 C6 C7 -171.4(4) . . . . ?
N1 C5 C4 C3 -0.6(6) . . . . ?
C5 N1 C1 C2 0.1(6) . . . . ?
C5 C6 C7 C8 177.4(4) . . . . ?
C5 C4 C3 C2 1.4(7) . . . . ?
C5 C4 C3 C11 -179.1(5) . . . . ?
N2 C6 C7 C8 0.1(6) . . . . ?
N2 C10 C9 C8 -0.6(8) . . . . ?
C6 C5 C4 C3 179.8(4) . . . . ?
C6 N2 C10 C9 2.2(7) . . . . ?
C6 C7 C8 C9 1.5(7) . . . . ?
C6 C7 C8 C12 -175.5(5) . . . . ?
C4 C5 C6 N2 -174.3(4) . . . . ?
C4 C5 C6 C7 8.2(7) . . . . ?
C4 C3 C11 F2 5.1(13) . . . . ?
C4 C3 C11 F1 119.2(7) . . . . ?
C4 C3 C11 F3 -133.0(10) . . . . ?
C4 C3 C11 F1A 158.6(8) . . . . ?
C4 C3 C11 F3A -85.8(7) . . . . ?
C4 C3 C11 F2A 28.6(11) . . . . ?
C2 C3 C11 F2 -175.4(11) . . . . ?
C2 C3 C11 F1 -61.3(8) . . . . ?
C2 C3 C11 F3 46.5(12) . . . . ?
C2 C3 C11 F1A -21.9(11) . . . . ?
C2 C3 C11 F3A 93.7(7) . . . . ?
C2 C3 C11 F2A -151.9(9) . . . . ?
C22 C13 C14 C15 2.9(7) . . . . ?
C22 C17 C16 C15 1.7(7) . . . . ?
C1 N1 C5 C6 179.5(4) . . . . ?
C1 N1 C5 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 -1.4(7) . . . . ?
C1 C2 C3 C11 179.1(5) . . . . ?
C19 C20 C21 O2 -179.0(5) . . . . ?
C19 C20 C21 C22 1.5(7) . . . . ?
C19 C18 C17 C22 2.1(7) . . . . ?
C19 C18 C17 C16 -176.9(5) . . . . ?
C3 C2 C1 N1 0.6(7) . . . . ?
C20 C19 C18 O3 176.7(6) . . . . ?
C20 C19 C18 C17 -2.6(7) . . . . ?
C21 C22 C17 C18 0.2(7) . . . . ?
C21 C22 C17 C16 179.1(4) . . . . ?
C14 C13 C22 C21 178.7(4) . . . . ?
C14 C13 C22 C17 -3.3(6) . . . . ?
C14 C15 C16 C17 -2.2(8) . . . . ?
C10 N2 C6 C5 -179.5(4) . . . . ?
C10 N2 C6 C7 -1.9(6) . . . . ?
C10 C9 C8 C7 -1.2(8) . . . . ?
C10 C9 C8 C12 175.8(5) . . . . ?
O3 C18 C17 C22 -177.2(5) . . . . ?
O3 C18 C17 C16 3.8(8) . . . . ?
C18 C19 C20 C21 0.9(8) . . . . ?
C18 C17 C16 C15 -179.3(5) . . . . ?
C17 C22 C21 O2 178.6(4) . . . . ?
C17 C22 C21 C20 -1.9(6) . . . . ?
F5 C12 C8 C7 -135.8(6) . . . . ?
F5 C12 C8 C9 47.2(8) . . . . ?
F4 C12 C8 C7 -17.1(9) . . . . ?
F4 C12 C8 C9 165.9(7) . . . . ?
C23 C19 C20 C21 179.8(5) . . . . ?
C23 C19 C18 O3 -2.3(8) . . . . ?
C23 C19 C18 C17 178.4(5) . . . . ?
F6 C12 C8 C7 105.0(8) . . . . ?
F6 C12 C8 C9 -72.0(8) . . . . ?
F4A C12 C8 C7 58.7(11) . . . . ?
F4A C12 C8 C9 -118.3(10) . . . . ?
F6A C12 C8 C7 168.2(11) . . . . ?
F6A C12 C8 C9 -8.8(13) . . . . ?
F5A C12 C8 C7 -50.5(11) . . . . ?
F5A C12 C8 C9 132.5(9) . . . . ?

_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_20190911-p-4-cuclo4aaa
_database_code_depnum_ccdc_archive 'CCDC 2222144'
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-11
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H19 Cu N2 O3, Cl O4'
_chemical_formula_sum            'C23 H19 Cl Cu N2 O7'
_chemical_formula_weight         534.39
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.3791(2)
_cell_length_b                   10.6291(2)
_cell_length_c                   22.1108(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.1043(17)
_cell_angle_gamma                90
_cell_volume                     2202.78(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5362
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.3460
_cell_measurement_theta_min      3.4450
_shelx_estimated_absorpt_T_max   0.873
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74082
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1092
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            13491
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.455
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_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  94.00   1.00    5.00    --   17.93-178.00   0.00   60
  2  ω    -20.00  60.00   1.00    5.00    --   17.93 -99.00 -30.00   80
  3  ω     -3.00  87.00   1.00    5.00    --   17.93  57.00 -90.00   90
  4  ω    -52.00  49.00   1.00    5.00    --  -19.72  19.00-150.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0648891000
_diffrn_orient_matrix_UB_12      0.0230110000
_diffrn_orient_matrix_UB_13      -0.0132235000
_diffrn_orient_matrix_UB_21      -0.0152905000
_diffrn_orient_matrix_UB_22      -0.0605557000
_diffrn_orient_matrix_UB_23      -0.0120945000
_diffrn_orient_matrix_UB_31      -0.0358088000
_diffrn_orient_matrix_UB_32      -0.0160664000
_diffrn_orient_matrix_UB_33      0.0266279000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3842
_reflns_number_total             4498
_reflns_odcompleteness_completeness 99.66
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     347
_refine_ls_number_reflns         4498
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.040
_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)+(0.0458P)²+1.4824P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0922
_refine_ls_wR_factor_ref         0.0985
_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. Others
 Sof(O7)=Sof(O4)=Sof(O9)=Sof(O5)=1-FVAR(1)
 Sof(O8)=Sof(O6)=Sof(O10)=Sof(O11)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C8(H8), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C21(H21)
3.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C10(H10A,H10B,H10C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.39835(3) 0.12709(3) 0.02721(2) 0.03253(11) Uani 1 1 d . . . . .
O2 O 0.37066(17) 0.01806(17) -0.04036(7) 0.0367(4) Uani 1 1 d . . . . .
O3 O 0.27299(17) 0.02784(16) 0.07521(7) 0.0358(4) Uani 1 1 d . . . . .
O1 O -0.16893(19) -0.2604(2) 0.00863(9) 0.0526(5) Uani 1 1 d . . . . .
N1 N 0.5189(2) 0.24471(19) -0.01746(8) 0.0323(4) Uani 1 1 d . . . . .
N2 N 0.4468(2) 0.24363(19) 0.09429(8) 0.0335(4) Uani 1 1 d . . . . .
C1 C 0.5504(3) 0.2356(2) -0.07592(11) 0.0378(5) Uani 1 1 d . . . . .
H1 H 0.503663 0.175648 -0.100013 0.045 Uiso 1 1 calc R U . . .
C2 C 0.6497(3) 0.3123(3) -0.10125(12) 0.0431(6) Uani 1 1 d . . . . .
H2 H 0.669225 0.304020 -0.141990 0.052 Uiso 1 1 calc R U . . .
C3 C 0.7210(3) 0.4022(2) -0.06622(13) 0.0440(6) Uani 1 1 d . . . . .
C4 C 0.8340(4) 0.4838(3) -0.09142(16) 0.0673(9) Uani 1 1 d . . . . .
H4A H 0.882694 0.438381 -0.122004 0.101 Uiso 1 1 calc R U . . .
H4B H 0.900957 0.507551 -0.059580 0.101 Uiso 1 1 calc R U . . .
H4C H 0.790946 0.557932 -0.108892 0.101 Uiso 1 1 calc R U . . .
C5 C 0.6845(3) 0.4131(2) -0.00608(12) 0.0413(6) Uani 1 1 d . . . . .
H5 H 0.728008 0.473831 0.018590 0.050 Uiso 1 1 calc R U . . .
C6 C 0.5837(2) 0.3336(2) 0.01694(11) 0.0328(5) Uani 1 1 d . . . . .
C7 C 0.5381(2) 0.3368(2) 0.08033(11) 0.0330(5) Uani 1 1 d . . . . .
C8 C 0.5821(3) 0.4252(3) 0.12236(12) 0.0421(6) Uani 1 1 d . . . . .
H8 H 0.646061 0.487559 0.111700 0.051 Uiso 1 1 calc R U . . .
C9 C 0.5318(3) 0.4220(3) 0.18068(12) 0.0481(7) Uani 1 1 d . . . . .
C10 C 0.5761(4) 0.5201(4) 0.22658(15) 0.0741(10) Uani 1 1 d . . . . .
H10A H 0.659246 0.491787 0.249229 0.111 Uiso 1 1 calc R U . . .
H10B H 0.499806 0.534013 0.253592 0.111 Uiso 1 1 calc R U . . .
H10C H 0.597398 0.597277 0.206219 0.111 Uiso 1 1 calc R U . . .
C11 C 0.4386(3) 0.3265(3) 0.19378(12) 0.0515(7) Uani 1 1 d . . . . .
H11 H 0.402155 0.321208 0.232248 0.062 Uiso 1 1 calc R U . . .
C12 C 0.3988(3) 0.2387(3) 0.15056(11) 0.0435(6) Uani 1 1 d . . . . .
H12 H 0.336902 0.174308 0.160716 0.052 Uiso 1 1 calc R U . . .
C13 C 0.2600(2) -0.0531(2) -0.05057(10) 0.0308(5) Uani 1 1 d . . . . .
C14 C 0.2371(3) -0.1004(2) -0.11031(10) 0.0362(5) Uani 1 1 d . . . . .
H14 H 0.300923 -0.079765 -0.139948 0.043 Uiso 1 1 calc R U . . .
C15 C 0.1232(3) -0.1755(3) -0.12482(11) 0.0413(6) Uani 1 1 d . . . . .
H15 H 0.110100 -0.205256 -0.164188 0.050 Uiso 1 1 calc R U . . .
C16 C 0.0260(3) -0.2082(2) -0.08118(11) 0.0387(6) Uani 1 1 d . . . . .
H16 H -0.052477 -0.258034 -0.091855 0.046 Uiso 1 1 calc R U . . .
C17 C 0.0454(3) -0.1672(2) -0.02266(11) 0.0332(5) Uani 1 1 d . . . . .
C18 C -0.0582(3) -0.2054(2) 0.02321(11) 0.0371(5) Uani 1 1 d . . . . .
C19 C -0.0254(3) -0.1750(2) 0.08761(11) 0.0372(5) Uani 1 1 d . . . . .
C20 C -0.1238(3) -0.2259(3) 0.13352(13) 0.0534(7) Uani 1 1 d . . . . .
H20A H -0.090232 -0.201472 0.173332 0.080 Uiso 1 1 calc R U . . .
H20B H -0.126366 -0.316073 0.130849 0.080 Uiso 1 1 calc R U . . .
H20C H -0.218030 -0.192938 0.125786 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0875(3) -0.1018(2) 0.10127(11) 0.0370(5) Uani 1 1 d . . . . .
H21 H 0.107725 -0.083272 0.141782 0.044 Uiso 1 1 calc R U . . .
C22 C 0.1803(2) -0.0496(2) 0.05619(10) 0.0307(5) Uani 1 1 d . . . . .
C23 C 0.1632(2) -0.0885(2) -0.00601(10) 0.0289(5) Uani 1 1 d . . . . .
Cl1 Cl 0.46176(12) -0.07279(10) 0.24651(4) 0.0738(3) Uani 1 1 d . . . . .
O8 O 0.5530(7) -0.0442(9) 0.2978(3) 0.118(3) Uani 0.650(10) 1 d . . P A 1
O6 O 0.4074(9) -0.1887(7) 0.2587(5) 0.137(3) Uani 0.650(10) 1 d . . P A 1
O10 O 0.3407(8) 0.0137(8) 0.2480(4) 0.150(4) Uani 0.650(10) 1 d . . P A 1
O11 O 0.5304(8) -0.0558(10) 0.1946(3) 0.124(3) Uani 0.650(10) 1 d . . P A 1
O7 O 0.5081(19) 0.0443(13) 0.2633(8) 0.163(7) Uani 0.350(10) 1 d . . P A 2
O4 O 0.3432(15) -0.0742(16) 0.2053(6) 0.150(6) Uani 0.350(10) 1 d . . P A 2
O9 O 0.439(2) -0.150(2) 0.2924(5) 0.155(10) Uani 0.350(10) 1 d . . P A 2
O5 O 0.5790(16) -0.1417(14) 0.2130(7) 0.121(5) Uani 0.350(10) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9010(16) . ?
Cu1 O3 1.9271(16) . ?
Cu1 N1 1.9744(19) . ?
Cu1 N2 1.9727(19) . ?
O2 C13 1.297(3) . ?
O3 C22 1.258(3) . ?
O1 C18 1.224(3) . ?
N1 C1 1.340(3) . ?
N1 C6 1.344(3) . ?
N2 C7 1.353(3) . ?
N2 C12 1.340(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.373(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.386(4) . ?
C3 C4 1.493(4) . ?
C3 C5 1.390(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C6 1.379(3) . ?
C6 C7 1.481(3) . ?
C7 C8 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.390(4) . ?
C9 C10 1.503(4) . ?
C9 C11 1.378(4) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.377(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.422(3) . ?
C13 C23 1.415(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.362(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.396(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.371(3) . ?
C17 C18 1.487(3) . ?
C17 C23 1.423(3) . ?
C18 C19 1.482(3) . ?
C19 C20 1.498(3) . ?
C19 C21 1.339(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21 0.9300 . ?
C21 C22 1.457(3) . ?
C22 C23 1.439(3) . ?
Cl1 O8 1.428(6) . ?
Cl1 O6 1.364(7) . ?
Cl1 O10 1.463(6) . ?
Cl1 O11 1.349(5) . ?
Cl1 O7 1.366(10) . ?
Cl1 O4 1.412(10) . ?
Cl1 O9 1.324(13) . ?
Cl1 O5 1.535(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O3 91.75(7) . . ?
O2 Cu1 N1 93.27(7) . . ?
O2 Cu1 N2 174.14(7) . . ?
O3 Cu1 N1 173.86(8) . . ?
O3 Cu1 N2 93.31(7) . . ?
N2 Cu1 N1 81.86(8) . . ?
C13 O2 Cu1 125.28(14) . . ?
C22 O3 Cu1 127.01(15) . . ?
C1 N1 Cu1 125.98(17) . . ?
C1 N1 C6 119.0(2) . . ?
C6 N1 Cu1 114.67(15) . . ?
C7 N2 Cu1 114.73(15) . . ?
C12 N2 Cu1 126.72(17) . . ?
C12 N2 C7 118.5(2) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.8(2) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 C5 117.5(2) . . ?
C5 C3 C4 120.8(3) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5 120.1 . . ?
C6 C5 C3 119.9(2) . . ?
C6 C5 H5 120.1 . . ?
N1 C6 C5 121.6(2) . . ?
N1 C6 C7 114.3(2) . . ?
C5 C6 C7 124.1(2) . . ?
N2 C7 C6 114.0(2) . . ?
N2 C7 C8 121.6(2) . . ?
C8 C7 C6 124.5(2) . . ?
C7 C8 H8 119.8 . . ?
C7 C8 C9 120.5(3) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 121.0(3) . . ?
C11 C9 C8 116.9(2) . . ?
C11 C9 C10 122.1(3) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11 119.6 . . ?
C12 C11 C9 120.8(3) . . ?
C12 C11 H11 119.6 . . ?
N2 C12 C11 121.7(3) . . ?
N2 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
O2 C13 C14 117.4(2) . . ?
O2 C13 C23 124.3(2) . . ?
C23 C13 C14 118.3(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.7 . . ?
C14 C15 C16 120.6(2) . . ?
C16 C15 H15 119.7 . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.4(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C18 119.3(2) . . ?
C16 C17 C23 120.4(2) . . ?
C23 C17 C18 120.3(2) . . ?
O1 C18 C17 121.3(2) . . ?
O1 C18 C19 120.1(2) . . ?
C19 C18 C17 118.6(2) . . ?
C18 C19 C20 117.4(2) . . ?
C21 C19 C18 118.6(2) . . ?
C21 C19 C20 124.0(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21 118.2 . . ?
C19 C21 C22 123.7(2) . . ?
C22 C21 H21 118.2 . . ?
O3 C22 C21 116.3(2) . . ?
O3 C22 C23 124.0(2) . . ?
C23 C22 C21 119.7(2) . . ?
C13 C23 C17 119.2(2) . . ?
C13 C23 C22 122.5(2) . . ?
C17 C23 C22 118.3(2) . . ?
O8 Cl1 O10 107.0(5) . . ?
O6 Cl1 O8 104.6(5) . . ?
O6 Cl1 O10 105.5(5) . . ?
O11 Cl1 O8 110.9(4) . . ?
O11 Cl1 O6 118.9(5) . . ?
O11 Cl1 O10 109.3(4) . . ?
O7 Cl1 O4 114.8(10) . . ?
O7 Cl1 O5 109.8(9) . . ?
O4 Cl1 O5 104.2(8) . . ?
O9 Cl1 O7 114.3(11) . . ?
O9 Cl1 O4 110.2(12) . . ?
O9 Cl1 O5 102.3(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O2 C13 C14 162.48(17) . . . . ?
Cu1 O2 C13 C23 -18.9(3) . . . . ?
Cu1 O3 C22 C21 -172.96(16) . . . . ?
Cu1 O3 C22 C23 7.6(3) . . . . ?
Cu1 N1 C1 C2 -171.42(19) . . . . ?
Cu1 N1 C6 C5 172.09(19) . . . . ?
Cu1 N1 C6 C7 -7.5(3) . . . . ?
Cu1 N2 C7 C6 0.3(3) . . . . ?
Cu1 N2 C7 C8 -179.83(19) . . . . ?
Cu1 N2 C12 C11 -179.2(2) . . . . ?
O2 C13 C14 C15 -179.8(2) . . . . ?
O2 C13 C23 C17 -180.0(2) . . . . ?
O2 C13 C23 C22 -1.1(4) . . . . ?
O3 C22 C23 C13 7.1(4) . . . . ?
O3 C22 C23 C17 -174.0(2) . . . . ?
O1 C18 C19 C20 6.4(4) . . . . ?
O1 C18 C19 C21 -172.0(3) . . . . ?
N1 C1 C2 C3 0.2(4) . . . . ?
N1 C6 C7 N2 4.8(3) . . . . ?
N1 C6 C7 C8 -175.1(2) . . . . ?
N2 C7 C8 C9 -0.9(4) . . . . ?
C1 N1 C6 C5 -1.8(4) . . . . ?
C1 N1 C6 C7 178.6(2) . . . . ?
C1 C2 C3 C4 177.4(3) . . . . ?
C1 C2 C3 C5 -1.9(4) . . . . ?
C2 C3 C5 C6 1.8(4) . . . . ?
C3 C5 C6 N1 0.0(4) . . . . ?
C3 C5 C6 C7 179.6(2) . . . . ?
C4 C3 C5 C6 -177.5(3) . . . . ?
C5 C6 C7 N2 -174.8(2) . . . . ?
C5 C6 C7 C8 5.3(4) . . . . ?
C6 N1 C1 C2 1.7(4) . . . . ?
C6 C7 C8 C9 179.0(2) . . . . ?
C7 N2 C12 C11 0.8(4) . . . . ?
C7 C8 C9 C10 -178.3(3) . . . . ?
C7 C8 C9 C11 0.7(4) . . . . ?
C8 C9 C11 C12 0.3(5) . . . . ?
C9 C11 C12 N2 -1.0(5) . . . . ?
C10 C9 C11 C12 179.3(3) . . . . ?
C12 N2 C7 C6 -179.8(2) . . . . ?
C12 N2 C7 C8 0.2(4) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C14 C13 C23 C17 -1.4(3) . . . . ?
C14 C13 C23 C22 177.5(2) . . . . ?
C14 C15 C16 C17 -1.4(4) . . . . ?
C15 C16 C17 C18 -178.8(2) . . . . ?
C15 C16 C17 C23 1.5(4) . . . . ?
C16 C17 C18 O1 -8.5(4) . . . . ?
C16 C17 C18 C19 171.9(2) . . . . ?
C16 C17 C23 C13 -0.1(4) . . . . ?
C16 C17 C23 C22 -179.0(2) . . . . ?
C17 C18 C19 C20 -173.9(2) . . . . ?
C17 C18 C19 C21 7.7(4) . . . . ?
C18 C17 C23 C13 -179.8(2) . . . . ?
C18 C17 C23 C22 1.3(3) . . . . ?
C18 C19 C21 C22 0.2(4) . . . . ?
C19 C21 C22 O3 172.9(2) . . . . ?
C19 C21 C22 C23 -7.6(4) . . . . ?
C20 C19 C21 C22 -178.1(2) . . . . ?
C21 C22 C23 C13 -172.3(2) . . . . ?
C21 C22 C23 C17 6.6(3) . . . . ?
C23 C13 C14 C15 1.5(4) . . . . ?
C23 C17 C18 O1 171.2(2) . . . . ?
C23 C17 C18 C19 -8.4(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.677
####################################################################### 
# 
# 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_20200709-ccf-zhq-pp-4nh2-cuclo4-meoh-ch3cnaaa
_database_code_depnum_ccdc_archive 'CCDC 2222146'
_audit_update_record             
;
2022-11-25 deposited with the CCDC.	2024-01-05 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Cu N4 O3, Cl O4'
_chemical_formula_sum            'C21 H17 Cl Cu N4 O7'
_chemical_formula_weight         536.38
_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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   9.4798(5)
_cell_length_b                   10.4607(8)
_cell_length_c                   12.3592(8)
_cell_angle_alpha                109.072(7)
_cell_angle_beta                 110.542(6)
_cell_angle_gamma                90.238(5)
_cell_volume                     1074.86(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1872
_cell_measurement_temperature    298
_cell_measurement_theta_max      21.8200
_cell_measurement_theta_min      4.1520
_shelx_estimated_absorpt_T_max   0.870
_shelx_estimated_absorpt_T_min   0.739
_exptl_absorpt_coefficient_mu    1.194
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79401
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dull brownish brown'
_exptl_crystal_colour_lustre     dull
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             546
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0872
_diffrn_reflns_av_unetI/netI     0.1274
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16062
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.806
_diffrn_reflns_theta_min         3.255
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9784
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00  48.00   1.00   16.00    --   17.77 -77.00 -30.00  100
  2  ω    -20.00  60.00   1.00   16.00    --   17.77 -99.00-120.00   80
  3  ω     -8.00  90.00   1.00   16.00    --   17.77  38.00-120.00   98
  4  ω    -12.00  88.00   1.00   16.00    --   17.77  77.00  90.00  100
  5  ω    -64.00  53.00   1.00   16.00    --  -19.57  19.00 -90.00  117
  6  ω     -4.00  87.00   1.00   16.00    --   17.77  57.00 -30.00   91
  7  ω    -20.00  56.00   1.00   16.00    --   17.77 -99.00  60.00   76
  8  ω    -51.00  38.00   1.00   16.00    --   17.77 -57.00  90.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0123784000
_diffrn_orient_matrix_UB_12      0.0722489000
_diffrn_orient_matrix_UB_13      0.0197849000
_diffrn_orient_matrix_UB_21      -0.0497512000
_diffrn_orient_matrix_UB_22      -0.0026192000
_diffrn_orient_matrix_UB_23      -0.0591971000
_diffrn_orient_matrix_UB_31      -0.0622346000
_diffrn_orient_matrix_UB_32      0.0038717000
_diffrn_orient_matrix_UB_33      0.0196585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2551
_reflns_number_total             5050
_reflns_odcompleteness_completeness 99.82
_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 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.634
_refine_diff_density_min         -0.577
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     309
_refine_ls_number_reflns         5050
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1551
_refine_ls_R_factor_gt           0.0708
_refine_ls_restrained_S_all      1.001
_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)+(0.0762P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1518
_refine_ls_wR_factor_ref         0.1959
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1BA(H1BA), C3BA(H3BA), C4BA(H4BA), C5BA(H5BA), C6BA(H6BA), C7BA(H7BA),
 C9BA(H9BA), C7AA(H7AA), C8AA(H8AA), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
2.d Idealised Me refined as rotating group:
 C0BA(H0BA,H0BB,H0BC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_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 0.91965(7) 0.89470(7) 0.55562(6) 0.0405(3) Uani 1 1 d . . . . .
Cl2 Cl 1.2109(2) 0.30995(19) -0.00636(17) 0.0733(6) Uani 1 1 d . . . . .
C5 C 0.7198(6) 1.0935(5) 0.6042(5) 0.0385(13) Uani 1 1 d . . . . .
N4 N 1.0091(5) 0.7444(4) 0.4731(4) 0.0337(10) Uani 1 1 d . . . . .
C7 C 0.7160(6) 1.0097(5) 0.3891(5) 0.0383(13) Uani 1 1 d . . . . .
N3 N 1.0185(5) 0.8343(5) 0.6950(4) 0.0411(11) Uani 1 1 d . . . . .
O3 O 0.3486(5) 1.2852(5) 0.5009(4) 0.0678(13) Uani 1 1 d . . . . .
C1BA C 0.9993(6) 0.7064(5) 0.3543(5) 0.0408(13) Uani 1 1 d . . . . .
H1BA H 0.935239 0.747001 0.302582 0.049 Uiso 1 1 calc R U . . .
C3BA C 0.6446(6) 1.0069(6) 0.2670(5) 0.0457(14) Uani 1 1 d . . . . .
H3BA H 0.682460 0.958544 0.207724 0.055 Uiso 1 1 calc R U . . .
C4BA C 0.4620(6) 1.1449(6) 0.3203(5) 0.0487(15) Uani 1 1 d . . . . .
H4BA H 0.376369 1.187396 0.296333 0.058 Uiso 1 1 calc R U . . .
C5BA C 1.0804(6) 0.6107(5) 0.3084(5) 0.0416(13) Uani 1 1 d . . . . .
H5BA H 1.071213 0.586995 0.226651 0.050 Uiso 1 1 calc R U . . .
C6BA C 0.5219(7) 1.0728(6) 0.2333(6) 0.0536(16) Uani 1 1 d . . . . .
H6BA H 0.478032 1.069766 0.152264 0.064 Uiso 1 1 calc R U . . .
C7BA C 1.1611(6) 0.6683(6) 0.7573(5) 0.0454(14) Uani 1 1 d . . . . .
H7BA H 1.218289 0.597837 0.739856 0.054 Uiso 1 1 calc R U . . .
C8BA C 0.5291(6) 1.1534(5) 0.4416(5) 0.0396(13) Uani 1 1 d . . . . .
C9BA C 1.0063(7) 0.8810(6) 0.8064(5) 0.0512(15) Uani 1 1 d . . . . .
H9BA H 0.954756 0.955810 0.824094 0.061 Uiso 1 1 calc R U . . .
C1AA C 1.1428(7) 0.7104(6) 0.8696(6) 0.0562(16) Uani 1 1 d . . . . .
C2AA C 1.0984(6) 0.6809(5) 0.5451(5) 0.0361(12) Uani 1 1 d . . . . .
C3AA C 1.0971(6) 0.7276(5) 0.6724(5) 0.0394(13) Uani 1 1 d . . . . .
N2 N 1.2647(6) 0.4569(5) 0.3425(5) 0.0663(16) Uani 1 1 d . . . . .
H2A H 1.248583 0.382652 0.354730 0.080 Uiso 1 1 d R U . . .
H2B H 1.239951 0.439611 0.264559 0.080 Uiso 1 1 d R U . . .
C5AA C 0.4667(6) 1.2326(6) 0.5334(5) 0.0446(14) Uani 1 1 d . . . . .
C6AA C 0.5411(6) 1.2471(6) 0.6634(5) 0.0448(14) Uani 1 1 d . . . . .
C7AA C 0.6617(6) 1.1798(6) 0.6937(5) 0.0444(14) Uani 1 1 d . . . . .
H7AA H 0.710302 1.189079 0.776141 0.053 Uiso 1 1 calc R U . . .
C8AA C 1.1818(6) 0.5832(5) 0.5043(5) 0.0433(14) Uani 1 1 d . . . . .
H8AA H 1.241025 0.540428 0.556215 0.052 Uiso 1 1 calc R U . . .
C9AA C 0.6563(5) 1.0847(5) 0.4776(5) 0.0352(12) Uani 1 1 d . . . . .
C0BA C 0.4787(7) 1.3346(6) 0.7531(5) 0.0581(17) Uani 1 1 d . . . . .
H0BA H 0.492696 1.427663 0.758417 0.087 Uiso 1 1 calc R U . . .
H0BB H 0.530977 1.328089 0.832836 0.087 Uiso 1 1 calc R U . . .
H0BC H 0.372251 1.304328 0.725993 0.087 Uiso 1 1 calc R U . . .
N1 N 1.1942(6) 0.6468(6) 0.9514(5) 0.0721(17) Uani 1 1 d . . . . .
H1A H 1.240662 0.576762 0.935103 0.086 Uiso 1 1 calc R U . . .
H1B H 1.180715 0.676035 1.020232 0.086 Uiso 1 1 calc R U . . .
C1 C 1.1767(6) 0.5486(6) 0.3837(5) 0.0462(14) Uani 1 1 d . . . . .
O7 O 1.2865(7) 0.3517(6) -0.0705(5) 0.111(2) Uani 1 1 d . . . . .
C3 C 1.0654(7) 0.8244(6) 0.8931(6) 0.0582(17) Uani 1 1 d . . . . .
H3 H 1.054930 0.860759 0.968918 0.070 Uiso 1 1 calc R U . . .
O5 O 1.1735(8) 0.4228(6) 0.0689(6) 0.120(2) Uani 1 1 d . . . . .
O6 O 1.0730(11) 0.2327(9) -0.0907(6) 0.210(5) Uani 1 1 d . . . . .
O4 O 1.2861(11) 0.2410(11) 0.0639(9) 0.226(5) Uani 1 1 d . . . . .
O2 O 0.8325(4) 0.9435(4) 0.4136(3) 0.0418(9) Uani 1 1 d . . . . .
O1 O 0.8260(4) 1.0306(4) 0.6468(3) 0.0411(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 1.949(4) . ?
Cu1 N3 1.956(4) . ?
Cu1 O2 1.897(4) . ?
Cu1 O1 1.935(3) . ?
Cl2 O7 1.398(5) . ?
Cl2 O5 1.379(5) . ?
Cl2 O6 1.390(8) . ?
Cl2 O4 1.328(7) . ?
C5 C7AA 1.457(7) . ?
C5 C9AA 1.436(7) . ?
C5 O1 1.258(6) . ?
N4 C1BA 1.358(6) . ?
N4 C2AA 1.346(6) . ?
C7 C3BA 1.410(7) . ?
C7 C9AA 1.418(7) . ?
C7 O2 1.304(5) . ?
N3 C9BA 1.350(7) . ?
N3 C3AA 1.352(6) . ?
O3 C5AA 1.245(6) . ?
C1BA H1BA 0.9300 . ?
C1BA C5BA 1.362(7) . ?
C3BA H3BA 0.9300 . ?
C3BA C6BA 1.362(7) . ?
C4BA H4BA 0.9300 . ?
C4BA C6BA 1.396(7) . ?
C4BA C8BA 1.380(7) . ?
C5BA H5BA 0.9300 . ?
C5BA C1 1.387(7) . ?
C6BA H6BA 0.9300 . ?
C7BA H7BA 0.9300 . ?
C7BA C1AA 1.385(8) . ?
C7BA C3AA 1.355(7) . ?
C8BA C5AA 1.477(7) . ?
C8BA C9AA 1.417(7) . ?
C9BA H9BA 0.9300 . ?
C9BA C3 1.345(8) . ?
C1AA N1 1.342(7) . ?
C1AA C3 1.405(8) . ?
C2AA C3AA 1.492(7) . ?
C2AA C8AA 1.368(7) . ?
N2 H2A 0.8615 . ?
N2 H2B 0.8615 . ?
N2 C1 1.364(6) . ?
C5AA C6AA 1.466(8) . ?
C6AA C7AA 1.349(7) . ?
C6AA C0BA 1.489(7) . ?
C7AA H7AA 0.9300 . ?
C8AA H8AA 0.9300 . ?
C8AA C1 1.397(7) . ?
C0BA H0BA 0.9600 . ?
C0BA H0BB 0.9600 . ?
C0BA H0BC 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
C3 H3 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
N4 Cu1 N3 81.93(17) . . ?
O2 Cu1 N4 93.46(15) . . ?
O2 Cu1 N3 175.33(15) . . ?
O2 Cu1 O1 91.64(14) . . ?
O1 Cu1 N4 173.49(16) . . ?
O1 Cu1 N3 93.01(16) . . ?
O5 Cl2 O7 109.3(4) . . ?
O5 Cl2 O6 105.4(6) . . ?
O6 Cl2 O7 108.6(4) . . ?
O4 Cl2 O7 116.3(4) . . ?
O4 Cl2 O5 107.2(5) . . ?
O4 Cl2 O6 109.4(7) . . ?
C9AA C5 C7AA 120.3(5) . . ?
O1 C5 C7AA 115.1(5) . . ?
O1 C5 C9AA 124.6(5) . . ?
C1BA N4 Cu1 126.2(3) . . ?
C2AA N4 Cu1 115.7(3) . . ?
C2AA N4 C1BA 118.0(4) . . ?
C3BA C7 C9AA 117.8(5) . . ?
O2 C7 C3BA 118.1(5) . . ?
O2 C7 C9AA 124.1(5) . . ?
C9BA N3 Cu1 126.7(4) . . ?
C9BA N3 C3AA 117.5(5) . . ?
C3AA N3 Cu1 115.5(3) . . ?
N4 C1BA H1BA 118.9 . . ?
N4 C1BA C5BA 122.1(5) . . ?
C5BA C1BA H1BA 118.9 . . ?
C7 C3BA H3BA 119.0 . . ?
C6BA C3BA C7 122.0(5) . . ?
C6BA C3BA H3BA 119.0 . . ?
C6BA C4BA H4BA 119.8 . . ?
C8BA C4BA H4BA 119.8 . . ?
C8BA C4BA C6BA 120.4(5) . . ?
C1BA C5BA H5BA 120.0 . . ?
C1BA C5BA C1 120.0(5) . . ?
C1 C5BA H5BA 120.0 . . ?
C3BA C6BA C4BA 120.1(5) . . ?
C3BA C6BA H6BA 119.9 . . ?
C4BA C6BA H6BA 119.9 . . ?
C1AA C7BA H7BA 119.4 . . ?
C3AA C7BA H7BA 119.4 . . ?
C3AA C7BA C1AA 121.3(5) . . ?
C4BA C8BA C5AA 119.9(5) . . ?
C4BA C8BA C9AA 120.0(5) . . ?
C9AA C8BA C5AA 120.2(5) . . ?
N3 C9BA H9BA 118.5 . . ?
C3 C9BA N3 123.0(5) . . ?
C3 C9BA H9BA 118.5 . . ?
C7BA C1AA C3 115.9(5) . . ?
N1 C1AA C7BA 122.7(6) . . ?
N1 C1AA C3 121.4(6) . . ?
N4 C2AA C3AA 113.5(4) . . ?
N4 C2AA C8AA 122.7(5) . . ?
C8AA C2AA C3AA 123.8(5) . . ?
N3 C3AA C7BA 121.9(5) . . ?
N3 C3AA C2AA 113.0(5) . . ?
C7BA C3AA C2AA 125.1(5) . . ?
H2A N2 H2B 109.3 . . ?
C1 N2 H2A 109.3 . . ?
C1 N2 H2B 108.6 . . ?
O3 C5AA C8BA 120.5(5) . . ?
O3 C5AA C6AA 119.2(5) . . ?
C6AA C5AA C8BA 120.2(5) . . ?
C5AA C6AA C0BA 118.0(5) . . ?
C7AA C6AA C5AA 117.6(5) . . ?
C7AA C6AA C0BA 124.4(5) . . ?
C5 C7AA H7AA 118.3 . . ?
C6AA C7AA C5 123.5(5) . . ?
C6AA C7AA H7AA 118.3 . . ?
C2AA C8AA H8AA 120.4 . . ?
C2AA C8AA C1 119.2(5) . . ?
C1 C8AA H8AA 120.4 . . ?
C7 C9AA C5 122.3(4) . . ?
C8BA C9AA C5 118.0(5) . . ?
C8BA C9AA C7 119.7(5) . . ?
C6AA C0BA H0BA 109.5 . . ?
C6AA C0BA H0BB 109.5 . . ?
C6AA C0BA H0BC 109.5 . . ?
H0BA C0BA H0BB 109.5 . . ?
H0BA C0BA H0BC 109.5 . . ?
H0BB C0BA H0BC 109.5 . . ?
C1AA N1 H1A 120.0 . . ?
C1AA N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C5BA C1 C8AA 117.9(5) . . ?
N2 C1 C5BA 121.6(5) . . ?
N2 C1 C8AA 120.5(5) . . ?
C9BA C3 C1AA 120.3(6) . . ?
C9BA C3 H3 119.9 . . ?
C1AA C3 H3 119.9 . . ?
C7 O2 Cu1 126.8(3) . . ?
C5 O1 Cu1 127.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 N4 C1BA C5BA 171.9(4) . . . . ?
Cu1 N4 C2AA C3AA 6.9(6) . . . . ?
Cu1 N4 C2AA C8AA -173.1(4) . . . . ?
Cu1 N3 C9BA C3 172.9(5) . . . . ?
Cu1 N3 C3AA C7BA -174.7(4) . . . . ?
Cu1 N3 C3AA C2AA 2.7(6) . . . . ?
N4 Cu1 O2 C7 156.6(4) . . . . ?
N4 C1BA C5BA C1 0.0(8) . . . . ?
N4 C2AA C3AA N3 -6.2(7) . . . . ?
N4 C2AA C3AA C7BA 171.0(5) . . . . ?
N4 C2AA C8AA C1 1.0(8) . . . . ?
C7 C3BA C6BA C4BA -0.7(9) . . . . ?
N3 C9BA C3 C1AA -0.6(10) . . . . ?
O3 C5AA C6AA C7AA 174.8(5) . . . . ?
O3 C5AA C6AA C0BA -5.1(8) . . . . ?
C1BA N4 C2AA C3AA -178.3(4) . . . . ?
C1BA N4 C2AA C8AA 1.7(8) . . . . ?
C1BA C5BA C1 N2 -177.0(5) . . . . ?
C1BA C5BA C1 C8AA 2.7(8) . . . . ?
C3BA C7 C9AA C5 179.6(5) . . . . ?
C3BA C7 C9AA C8BA 0.0(8) . . . . ?
C3BA C7 O2 Cu1 -164.4(4) . . . . ?
C4BA C8BA C5AA O3 4.3(8) . . . . ?
C4BA C8BA C5AA C6AA -177.4(5) . . . . ?
C4BA C8BA C9AA C5 -178.4(5) . . . . ?
C4BA C8BA C9AA C7 1.2(8) . . . . ?
C6BA C4BA C8BA C5AA 178.6(5) . . . . ?
C6BA C4BA C8BA C9AA -2.2(9) . . . . ?
C7BA C1AA C3 C9BA 3.8(9) . . . . ?
C8BA C4BA C6BA C3BA 1.9(9) . . . . ?
C8BA C5AA C6AA C7AA -3.5(8) . . . . ?
C8BA C5AA C6AA C0BA 176.6(5) . . . . ?
C9BA N3 C3AA C7BA 0.4(8) . . . . ?
C9BA N3 C3AA C2AA 177.8(5) . . . . ?
C1AA C7BA C3AA N3 3.0(9) . . . . ?
C1AA C7BA C3AA C2AA -174.0(5) . . . . ?
C2AA N4 C1BA C5BA -2.3(8) . . . . ?
C2AA C8AA C1 C5BA -3.2(8) . . . . ?
C2AA C8AA C1 N2 176.5(5) . . . . ?
C3AA N3 C9BA C3 -1.6(9) . . . . ?
C3AA C7BA C1AA N1 174.5(6) . . . . ?
C3AA C7BA C1AA C3 -4.9(9) . . . . ?
C3AA C2AA C8AA C1 -178.9(5) . . . . ?
C5AA C8BA C9AA C5 0.8(8) . . . . ?
C5AA C8BA C9AA C7 -179.6(5) . . . . ?
C5AA C6AA C7AA C5 -0.6(8) . . . . ?
C7AA C5 C9AA C7 175.6(5) . . . . ?
C7AA C5 C9AA C8BA -4.9(8) . . . . ?
C7AA C5 O1 Cu1 173.8(3) . . . . ?
C8AA C2AA C3AA N3 173.8(5) . . . . ?
C8AA C2AA C3AA C7BA -9.0(9) . . . . ?
C9AA C5 C7AA C6AA 5.0(8) . . . . ?
C9AA C5 O1 Cu1 -6.1(8) . . . . ?
C9AA C7 C3BA C6BA -0.3(8) . . . . ?
C9AA C7 O2 Cu1 15.7(7) . . . . ?
C9AA C8BA C5AA O3 -174.9(5) . . . . ?
C9AA C8BA C5AA C6AA 3.4(8) . . . . ?
C0BA C6AA C7AA C5 179.3(5) . . . . ?
N1 C1AA C3 C9BA -175.7(6) . . . . ?
O2 C7 C3BA C6BA 179.8(5) . . . . ?
O2 C7 C9AA C5 -0.5(8) . . . . ?
O2 C7 C9AA C8BA 179.9(5) . . . . ?
O1 Cu1 O2 C7 -19.4(4) . . . . ?
O1 C5 C7AA C6AA -175.0(5) . . . . ?
O1 C5 C9AA C7 -4.5(8) . . . . ?
O1 C5 C9AA C8BA 175.1(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 1.437
_oxdiff_exptl_absorpt_empirical_full_min 0.773
