# Supplementary Information (SI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2026

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 2336936'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H21 N4 O3, Cl O4'
_chemical_formula_sum            'C18 H21 Cl N4 O7'
_chemical_formula_weight         440.84

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'
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'

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

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

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

_cell_length_a                   13.6826(5)
_cell_length_b                   9.7733(3)
_cell_length_c                   15.5906(6)
_cell_angle_alpha                90
_cell_angle_beta                 109.453(4)
_cell_angle_gamma                90
_cell_volume                     1965.83(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2851
_cell_measurement_theta_min      3.5980
_cell_measurement_theta_max      27.0840

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.91440
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            7516
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.407
_diffrn_reflns_theta_max         27.054
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3932
_reflns_number_gt                3295
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0588P)²+1.6042P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3932
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0558
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.59644(13) 0.5769(2) 0.68870(12) 0.0182(4) Uani 1 1 d . . . . .
H1 H 0.583(2) 0.495(3) 0.6817(17) 0.028(7) Uiso 1 1 d . . . . .
C2 C 0.54821(15) 0.6932(2) 0.65455(14) 0.0173(4) Uani 1 1 d . . . . .
N3 N 0.60873(13) 0.8001(2) 0.69207(12) 0.0183(4) Uani 1 1 d . . . . .
H3 H 0.5962(18) 0.884(3) 0.6853(15) 0.017(6) Uiso 1 1 d . . . . .
C4 C 0.70031(15) 0.7503(2) 0.75517(13) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.78684(16) 0.8178(2) 0.81216(14) 0.0213(5) Uani 1 1 d . . . . .
H5 H 0.791890 0.914735 0.813292 0.026 Uiso 1 1 calc R U . . .
C6 C 0.86557(16) 0.7359(2) 0.86736(15) 0.0236(5) Uani 1 1 d . . . . .
H6 H 0.925933 0.778079 0.907774 0.028 Uiso 1 1 calc R U . . .
C7 C 0.85875(16) 0.5937(2) 0.86531(15) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.914586 0.541292 0.903969 0.029 Uiso 1 1 calc R U . . .
C8 C 0.77180(16) 0.5268(2) 0.80779(14) 0.0218(5) Uani 1 1 d . . . . .
H8 H 0.766825 0.429793 0.806303 0.026 Uiso 1 1 calc R U . . .
C9 C 0.69316(15) 0.6079(2) 0.75303(13) 0.0180(4) Uani 1 1 d . . . . .
N10 N 0.45282(13) 0.69997(18) 0.59158(12) 0.0191(4) Uani 1 1 d . . . . .
N11 N 0.40984(13) 0.57192(18) 0.56351(11) 0.0178(4) Uani 1 1 d . . . . .
C12 C 0.31421(15) 0.5693(2) 0.51271(13) 0.0181(4) Uani 1 1 d . . . . .
H12 H 0.276832 0.652555 0.496132 0.022 Uiso 1 1 calc R U . . .
C13 C 0.26263(15) 0.4396(2) 0.48031(13) 0.0173(4) Uani 1 1 d . . . . .
O14 O 0.10307(11) 0.56258(15) 0.40960(9) 0.0197(3) Uani 1 1 d . . . . .
C14 C 0.15628(15) 0.4407(2) 0.42768(13) 0.0168(4) Uani 1 1 d . . . . .
O15 O 0.00052(11) 0.32112(16) 0.34428(10) 0.0222(3) Uani 1 1 d . . . . .
C15 C 0.10413(15) 0.3188(2) 0.39739(13) 0.0181(4) Uani 1 1 d . . . . .
C16 C 0.15617(16) 0.1942(2) 0.41789(14) 0.0201(4) Uani 1 1 d . . . . .
O16 O 0.09683(11) 0.08106(16) 0.38710(11) 0.0278(4) Uani 1 1 d . . . . .
C17 C 0.26221(16) 0.1920(2) 0.46882(14) 0.0202(4) Uani 1 1 d . . . . .
H17 H 0.298674 0.107685 0.481971 0.024 Uiso 1 1 calc R U . . .
C18 C 0.31305(15) 0.3138(2) 0.49965(14) 0.0193(4) Uani 1 1 d . . . . .
H18 H 0.384533 0.311612 0.535107 0.023 Uiso 1 1 calc R U . . .
C101 C 0.39378(17) 0.8270(2) 0.57194(15) 0.0225(5) Uani 1 1 d . . . . .
H10A H 0.364430 0.839720 0.505932 0.034 Uiso 1 1 calc R U . . .
H10B H 0.439594 0.903996 0.598923 0.034 Uiso 1 1 calc R U . . .
H10C H 0.337601 0.822761 0.597742 0.034 Uiso 1 1 calc R U . . .
C141 C 0.07433(17) 0.6030(2) 0.31499(14) 0.0241(5) Uani 1 1 d . . . . .
H14A H 0.048418 0.523133 0.276029 0.036 Uiso 1 1 calc R U . . .
H14B H 0.135108 0.640216 0.303143 0.036 Uiso 1 1 calc R U . . .
H14C H 0.020014 0.672966 0.301813 0.036 Uiso 1 1 calc R U . . .
C151 C -0.06867(16) 0.3190(3) 0.39540(17) 0.0280(5) Uani 1 1 d . . . . .
H15A H -0.140291 0.324713 0.353842 0.042 Uiso 1 1 calc R U . . .
H15B H -0.054006 0.397048 0.437217 0.042 Uiso 1 1 calc R U . . .
H15C H -0.059247 0.233676 0.430273 0.042 Uiso 1 1 calc R U . . .
C161 C 0.1483(2) -0.0474(3) 0.3964(2) 0.0472(8) Uani 1 1 d . . . . .
H16A H 0.203052 -0.042093 0.368957 0.071 Uiso 1 1 calc R U . . .
H16B H 0.098339 -0.118332 0.365625 0.071 Uiso 1 1 calc R U . . .
H16C H 0.179013 -0.070138 0.461086 0.071 Uiso 1 1 calc R U . . .
Cl1A Cl 0.39037(4) 0.68840(5) 0.81291(3) 0.02003(15) Uani 1 1 d . . . . .
O1A O 0.33693(16) 0.6248(2) 0.72689(13) 0.0453(5) Uani 1 1 d . . . . .
O2A O 0.44168(15) 0.58557(19) 0.87808(13) 0.0425(5) Uani 1 1 d . . . . .
O3A O 0.46366(12) 0.78616(17) 0.80110(12) 0.0288(4) Uani 1 1 d . . . . .
O4A O 0.31596(13) 0.75855(19) 0.84381(12) 0.0339(4) 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
N1 C2 1.333(3) . ?
N1 C9 1.402(3) . ?
N1 H1 0.82(3) . ?
C2 N3 1.340(3) . ?
C2 N10 1.348(3) . ?
N3 C4 1.398(3) . ?
N3 H3 0.84(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.394(3) . ?
C5 C6 1.387(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.380(3) . ?
C8 H8 0.9500 . ?
N10 N11 1.390(2) . ?
N10 C101 1.457(3) . ?
N11 C12 1.284(3) . ?
C12 C13 1.457(3) . ?
C12 H12 0.9500 . ?
C13 C18 1.393(3) . ?
C13 C14 1.413(3) . ?
O14 C14 1.375(2) . ?
O14 C141 1.449(2) . ?
C14 C15 1.389(3) . ?
O15 C15 1.383(2) . ?
O15 C151 1.426(3) . ?
C15 C16 1.393(3) . ?
C16 O16 1.361(3) . ?
C16 C17 1.403(3) . ?
O16 C161 1.423(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
Cl1A O2A 1.4353(18) . ?
Cl1A O4A 1.4371(16) . ?
Cl1A O1A 1.4377(18) . ?
Cl1A O3A 1.4406(16) . ?

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
C2 N1 C9 108.98(18) . . ?
C2 N1 H1 136.0(19) . . ?
C9 N1 H1 115.0(18) . . ?
N1 C2 N3 109.78(18) . . ?
N1 C2 N10 124.25(19) . . ?
N3 C2 N10 125.97(19) . . ?
C2 N3 C4 108.35(18) . . ?
C2 N3 H3 129.6(16) . . ?
C4 N3 H3 121.9(16) . . ?
C5 C4 C9 121.85(19) . . ?
C5 C4 N3 131.2(2) . . ?
C9 C4 N3 106.93(17) . . ?
C6 C5 C4 116.3(2) . . ?
C6 C5 H5 121.8 . . ?
C4 C5 H5 121.8 . . ?
C5 C6 C7 122.0(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C7 116.9(2) . . ?
C9 C8 H8 121.6 . . ?
C7 C8 H8 121.6 . . ?
C8 C9 C4 121.65(19) . . ?
C8 C9 N1 132.4(2) . . ?
C4 C9 N1 105.95(18) . . ?
C2 N10 N11 113.00(16) . . ?
C2 N10 C101 121.95(17) . . ?
N11 N10 C101 123.65(16) . . ?
C12 N11 N10 116.71(17) . . ?
N11 C12 C13 120.51(19) . . ?
N11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C18 C13 C14 118.19(19) . . ?
C18 C13 C12 123.04(18) . . ?
C14 C13 C12 118.77(19) . . ?
C14 O14 C141 112.97(15) . . ?
O14 C14 C15 119.77(17) . . ?
O14 C14 C13 119.88(18) . . ?
C15 C14 C13 120.29(19) . . ?
C15 O15 C151 113.81(16) . . ?
O15 C15 C14 119.84(18) . . ?
O15 C15 C16 119.69(18) . . ?
C14 C15 C16 120.44(18) . . ?
O16 C16 C15 115.47(18) . . ?
O16 C16 C17 124.76(19) . . ?
C15 C16 C17 119.76(19) . . ?
C16 O16 C161 117.64(17) . . ?
C18 C17 C16 119.34(19) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C13 121.97(18) . . ?
C17 C18 H18 119.0 . . ?
C13 C18 H18 119.0 . . ?
N10 C101 H10A 109.5 . . ?
N10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
N10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
O15 C151 H15A 109.5 . . ?
O15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
O15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16 C161 H16A 109.5 . . ?
O16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
O2A Cl1A O4A 109.33(11) . . ?
O2A Cl1A O1A 109.54(13) . . ?
O4A Cl1A O1A 108.79(12) . . ?
O2A Cl1A O3A 110.95(11) . . ?
O4A Cl1A O3A 109.11(10) . . ?
O1A Cl1A O3A 109.09(11) . . ?

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
C9 N1 C2 N3 0.9(2) . . . . ?
C9 N1 C2 N10 -179.22(19) . . . . ?
N1 C2 N3 C4 -1.2(2) . . . . ?
N10 C2 N3 C4 178.95(19) . . . . ?
C2 N3 C4 C5 -179.4(2) . . . . ?
C2 N3 C4 C9 1.0(2) . . . . ?
C9 C4 C5 C6 -0.4(3) . . . . ?
N3 C4 C5 C6 180.0(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C7 C8 C9 C4 0.0(3) . . . . ?
C7 C8 C9 N1 -179.6(2) . . . . ?
C5 C4 C9 C8 0.2(3) . . . . ?
N3 C4 C9 C8 179.89(19) . . . . ?
C5 C4 C9 N1 179.89(18) . . . . ?
N3 C4 C9 N1 -0.4(2) . . . . ?
C2 N1 C9 C8 179.4(2) . . . . ?
C2 N1 C9 C4 -0.3(2) . . . . ?
N1 C2 N10 N11 -1.5(3) . . . . ?
N3 C2 N10 N11 178.36(19) . . . . ?
N1 C2 N10 C101 165.42(19) . . . . ?
N3 C2 N10 C101 -14.7(3) . . . . ?
C2 N10 N11 C12 171.21(18) . . . . ?
C101 N10 N11 C12 4.5(3) . . . . ?
N10 N11 C12 C13 -179.80(17) . . . . ?
N11 C12 C13 C18 -1.8(3) . . . . ?
N11 C12 C13 C14 177.43(18) . . . . ?
C141 O14 C14 C15 -72.5(2) . . . . ?
C141 O14 C14 C13 110.3(2) . . . . ?
C18 C13 C14 O14 177.95(18) . . . . ?
C12 C13 C14 O14 -1.3(3) . . . . ?
C18 C13 C14 C15 0.7(3) . . . . ?
C12 C13 C14 C15 -178.57(18) . . . . ?
C151 O15 C15 C14 -88.8(2) . . . . ?
C151 O15 C15 C16 93.1(2) . . . . ?
O14 C14 C15 O15 4.1(3) . . . . ?
C13 C14 C15 O15 -178.64(17) . . . . ?
O14 C14 C15 C16 -177.74(18) . . . . ?
C13 C14 C15 C16 -0.5(3) . . . . ?
O15 C15 C16 O16 -3.7(3) . . . . ?
C14 C15 C16 O16 178.12(18) . . . . ?
O15 C15 C16 C17 177.57(18) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 O16 C161 172.5(2) . . . . ?
C17 C16 O16 C161 -8.9(3) . . . . ?
O16 C16 C17 C18 -177.1(2) . . . . ?
C15 C16 C17 C18 1.4(3) . . . . ?
C16 C17 C18 C13 -1.2(3) . . . . ?
C14 C13 C18 C17 0.2(3) . . . . ?
C12 C13 C18 C17 179.41(19) . . . . ?

_refine_diff_density_max         0.625
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_L2
_database_code_depnum_ccdc_archive 'CCDC 2336937'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H19 Cl N4 O7'
_chemical_formula_weight         438.82

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'
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'

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

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

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

_cell_length_a                   12.0808(2)
_cell_length_b                   8.7564(2)
_cell_length_c                   18.0332(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.440(2)
_cell_angle_gamma                90
_cell_volume                     1907.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    2993
_cell_measurement_theta_min      3.6260
_cell_measurement_theta_max      26.5290

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.528
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.89579
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            7258
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.072
_diffrn_reflns_theta_max         26.727
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3667
_reflns_number_gt                3229
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.7748P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3667
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.19002(11) 0.47222(17) 0.67341(8) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.28731(11) 0.49963(17) 0.63590(8) 0.0169(3) Uani 1 1 d . . . . .
C3 C 0.34765(13) 0.58990(19) 0.67885(9) 0.0151(3) Uani 1 1 d . . . . .
N4 N 0.29269(11) 0.61696(16) 0.74430(7) 0.0141(3) Uani 1 1 d . . . . .
C5 C 0.29359(13) 0.7014(2) 0.81127(9) 0.0155(4) Uani 1 1 d . . . . .
C6 C 0.36933(14) 0.8024(2) 0.84277(9) 0.0162(4) Uani 1 1 d . . . . .
H6 H 0.436833 0.826472 0.819519 0.019 Uiso 1 1 calc R U . . .
C7 C 0.34137(14) 0.8666(2) 0.91016(9) 0.0181(4) Uani 1 1 d . . . . .
H7 H 0.391002 0.936403 0.933815 0.022 Uiso 1 1 calc R U . . .
C8 C 0.24180(14) 0.8308(2) 0.94395(9) 0.0193(4) Uani 1 1 d . . . . .
H8 H 0.225537 0.876779 0.990129 0.023 Uiso 1 1 calc R U . . .
C9 C 0.16590(14) 0.7297(2) 0.91186(9) 0.0195(4) Uani 1 1 d . . . . .
H9 H 0.098392 0.705574 0.935094 0.023 Uiso 1 1 calc R U . . .
C10 C 0.19312(14) 0.66573(19) 0.84454(9) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.10259(15) 0.3770(2) 0.64121(10) 0.0233(4) Uani 1 1 d . . . . .
H11A H 0.079353 0.418312 0.592763 0.035 Uiso 1 1 calc R U . . .
H11B H 0.039286 0.375968 0.674141 0.035 Uiso 1 1 calc R U . . .
H11C H 0.130235 0.272704 0.635036 0.035 Uiso 1 1 calc R U . . .
N11 N 0.13320(12) 0.56491(17) 0.79789(8) 0.0168(3) Uani 1 1 d . . . . .
H11 H 0.0737(18) 0.518(3) 0.8068(12) 0.036(6) Uiso 1 1 d . . . . .
C12 C 0.19518(13) 0.54144(19) 0.73866(9) 0.0150(3) Uani 1 1 d . . . . .
C13 C 0.45254(14) 0.65791(19) 0.65728(9) 0.0155(4) Uani 1 1 d . . . . .
C14 C 0.54705(14) 0.65494(19) 0.70530(9) 0.0149(4) Uani 1 1 d . . . . .
O14 O 0.53107(9) 0.57899(14) 0.77022(6) 0.0176(3) Uani 1 1 d . . . . .
C141 C 0.60450(15) 0.5982(2) 0.83376(9) 0.0228(4) Uani 1 1 d . . . . .
H14A H 0.672902 0.540723 0.826160 0.034 Uiso 1 1 calc R U . . .
H14B H 0.568457 0.560112 0.878198 0.034 Uiso 1 1 calc R U . . .
H14C H 0.622063 0.706716 0.840125 0.034 Uiso 1 1 calc R U . . .
C15 C 0.64598(14) 0.71750(19) 0.68156(9) 0.0157(4) Uani 1 1 d . . . . .
O15 O 0.73995(9) 0.71883(14) 0.72658(6) 0.0186(3) Uani 1 1 d . . . . .
C151 C 0.82151(14) 0.6053(2) 0.70769(10) 0.0227(4) Uani 1 1 d . . . . .
H15A H 0.837293 0.612852 0.654774 0.034 Uiso 1 1 calc R U . . .
H15B H 0.792787 0.503235 0.718476 0.034 Uiso 1 1 calc R U . . .
H15C H 0.889712 0.622896 0.737015 0.034 Uiso 1 1 calc R U . . .
C16 C 0.65074(14) 0.78148(19) 0.60985(9) 0.0166(4) Uani 1 1 d . . . . .
O16 O 0.75201(10) 0.83600(14) 0.59201(6) 0.0213(3) Uani 1 1 d . . . . .
C161 C 0.76782(16) 0.8779(2) 0.51611(10) 0.0278(4) Uani 1 1 d . . . . .
H16A H 0.744793 0.793243 0.483689 0.042 Uiso 1 1 calc R U . . .
H16B H 0.846221 0.900564 0.508756 0.042 Uiso 1 1 calc R U . . .
H16C H 0.723256 0.968457 0.504038 0.042 Uiso 1 1 calc R U . . .
C17 C 0.55804(14) 0.7826(2) 0.56276(9) 0.0184(4) Uani 1 1 d . . . . .
H17 H 0.562036 0.825125 0.514423 0.022 Uiso 1 1 calc R U . . .
C18 C 0.45958(14) 0.7211(2) 0.58702(9) 0.0181(4) Uani 1 1 d . . . . .
H18 H 0.395912 0.722315 0.555008 0.022 Uiso 1 1 calc R U . . .
Cl1A Cl 0.08108(3) 0.84326(5) 0.62067(2) 0.01652(13) Uani 1 1 d . . . . .
O1A O 0.04374(11) 0.82378(16) 0.69595(7) 0.0263(3) Uani 1 1 d . . . . .
O2A O 0.19986(10) 0.83982(15) 0.62031(8) 0.0270(3) Uani 1 1 d . . . . .
O3A O 0.04149(11) 0.98967(15) 0.59464(8) 0.0296(3) Uani 1 1 d . . . . .
O4A O 0.03662(11) 0.72409(16) 0.57459(7) 0.0300(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
N1 C12 1.324(2) . ?
N1 N2 1.3916(19) . ?
N1 C11 1.455(2) . ?
N2 C3 1.314(2) . ?
C3 N4 1.389(2) . ?
C3 C13 1.462(2) . ?
N4 C12 1.353(2) . ?
N4 C5 1.416(2) . ?
C5 C6 1.384(2) . ?
C5 C10 1.403(2) . ?
C6 C7 1.388(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(2) . ?
C9 H9 0.9500 . ?
C10 N11 1.407(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N11 C12 1.336(2) . ?
N11 H11 0.85(2) . ?
C13 C18 1.387(2) . ?
C13 C14 1.416(2) . ?
C14 O14 1.3644(19) . ?
C14 C15 1.392(2) . ?
O14 C141 1.4412(19) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C15 O15 1.3790(19) . ?
C15 C16 1.412(2) . ?
O15 C151 1.446(2) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C16 O16 1.359(2) . ?
C16 C17 1.388(2) . ?
O16 C161 1.434(2) . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
Cl1A O4A 1.4302(13) . ?
Cl1A O2A 1.4354(13) . ?
Cl1A O3A 1.4428(13) . ?
Cl1A O1A 1.4512(13) . ?

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
C12 N1 N2 109.36(13) . . ?
C12 N1 C11 129.40(15) . . ?
N2 N1 C11 121.22(14) . . ?
C3 N2 N1 106.26(13) . . ?
N2 C3 N4 109.48(14) . . ?
N2 C3 C13 124.04(15) . . ?
N4 C3 C13 126.35(15) . . ?
C12 N4 C3 106.66(14) . . ?
C12 N4 C5 107.90(14) . . ?
C3 N4 C5 145.12(14) . . ?
C6 C5 C10 122.47(16) . . ?
C6 C5 N4 132.41(16) . . ?
C10 C5 N4 105.11(14) . . ?
C5 C6 C7 116.43(16) . . ?
C5 C6 H6 121.8 . . ?
C7 C6 H6 121.8 . . ?
C6 C7 C8 121.45(16) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 121.81(16) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C10 C9 C8 117.01(16) . . ?
C10 C9 H9 121.5 . . ?
C8 C9 H9 121.5 . . ?
C9 C10 C5 120.83(16) . . ?
C9 C10 N11 130.40(16) . . ?
C5 C10 N11 108.76(14) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 N11 C10 106.51(14) . . ?
C12 N11 H11 124.9(15) . . ?
C10 N11 H11 128.2(15) . . ?
N1 C12 N11 140.04(16) . . ?
N1 C12 N4 108.19(14) . . ?
N11 C12 N4 111.68(15) . . ?
C18 C13 C14 119.93(15) . . ?
C18 C13 C3 118.63(15) . . ?
C14 C13 C3 121.40(15) . . ?
O14 C14 C15 126.64(15) . . ?
O14 C14 C13 113.86(14) . . ?
C15 C14 C13 119.35(15) . . ?
C14 O14 C141 121.86(13) . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
O15 C15 C14 121.52(15) . . ?
O15 C15 C16 118.95(15) . . ?
C14 C15 C16 119.53(15) . . ?
C15 O15 C151 114.28(13) . . ?
O15 C151 H15A 109.5 . . ?
O15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
O15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16 C16 C17 124.72(15) . . ?
O16 C16 C15 114.44(14) . . ?
C17 C16 C15 120.82(16) . . ?
C16 O16 C161 117.25(13) . . ?
O16 C161 H16A 109.5 . . ?
O16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C18 C17 C16 119.30(16) . . ?
C18 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C17 C18 C13 121.06(16) . . ?
C17 C18 H18 119.5 . . ?
C13 C18 H18 119.5 . . ?
O4A Cl1A O2A 110.06(8) . . ?
O4A Cl1A O3A 110.04(9) . . ?
O2A Cl1A O3A 109.90(8) . . ?
O4A Cl1A O1A 109.68(8) . . ?
O2A Cl1A O1A 109.64(8) . . ?
O3A Cl1A O1A 107.48(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
C12 N1 N2 C3 -2.13(18) . . . . ?
C11 N1 N2 C3 179.23(15) . . . . ?
N1 N2 C3 N4 1.97(18) . . . . ?
N1 N2 C3 C13 -174.17(15) . . . . ?
N2 C3 N4 C12 -1.15(18) . . . . ?
C13 C3 N4 C12 174.88(16) . . . . ?
N2 C3 N4 C5 -173.2(2) . . . . ?
C13 C3 N4 C5 2.8(3) . . . . ?
C12 N4 C5 C6 -176.76(18) . . . . ?
C3 N4 C5 C6 -4.8(4) . . . . ?
C12 N4 C5 C10 1.93(18) . . . . ?
C3 N4 C5 C10 173.9(2) . . . . ?
C10 C5 C6 C7 0.6(2) . . . . ?
N4 C5 C6 C7 179.14(17) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
C7 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C5 0.6(2) . . . . ?
C8 C9 C10 N11 -177.84(16) . . . . ?
C6 C5 C10 C9 -0.9(3) . . . . ?
N4 C5 C10 C9 -179.76(15) . . . . ?
C6 C5 C10 N11 177.84(15) . . . . ?
N4 C5 C10 N11 -1.02(18) . . . . ?
C9 C10 N11 C12 178.32(17) . . . . ?
C5 C10 N11 C12 -0.27(18) . . . . ?
N2 N1 C12 N11 177.5(2) . . . . ?
C11 N1 C12 N11 -4.1(3) . . . . ?
N2 N1 C12 N4 1.43(18) . . . . ?
C11 N1 C12 N4 179.92(16) . . . . ?
C10 N11 C12 N1 -174.4(2) . . . . ?
C10 N11 C12 N4 1.56(19) . . . . ?
C3 N4 C12 N1 -0.21(18) . . . . ?
C5 N4 C12 N1 175.02(13) . . . . ?
C3 N4 C12 N11 -177.47(14) . . . . ?
C5 N4 C12 N11 -2.24(19) . . . . ?
N2 C3 C13 C18 44.3(2) . . . . ?
N4 C3 C13 C18 -131.19(18) . . . . ?
N2 C3 C13 C14 -133.24(17) . . . . ?
N4 C3 C13 C14 51.3(2) . . . . ?
C18 C13 C14 O14 -175.08(15) . . . . ?
C3 C13 C14 O14 2.4(2) . . . . ?
C18 C13 C14 C15 0.8(2) . . . . ?
C3 C13 C14 C15 178.27(15) . . . . ?
C15 C14 O14 C141 21.9(2) . . . . ?
C13 C14 O14 C141 -162.66(15) . . . . ?
O14 C14 C15 O15 -5.4(3) . . . . ?
C13 C14 C15 O15 179.30(15) . . . . ?
O14 C14 C15 C16 174.66(15) . . . . ?
C13 C14 C15 C16 -0.6(2) . . . . ?
C14 C15 O15 C151 103.56(18) . . . . ?
C16 C15 O15 C151 -76.54(19) . . . . ?
O15 C15 C16 O16 1.5(2) . . . . ?
C14 C15 C16 O16 -178.58(14) . . . . ?
O15 C15 C16 C17 -179.95(15) . . . . ?
C14 C15 C16 C17 0.0(2) . . . . ?
C17 C16 O16 C161 -9.1(2) . . . . ?
C15 C16 O16 C161 169.39(16) . . . . ?
O16 C16 C17 C18 178.91(16) . . . . ?
C15 C16 C17 C18 0.5(3) . . . . ?
C16 C17 C18 C13 -0.4(3) . . . . ?
C14 C13 C18 C17 -0.3(3) . . . . ?
C3 C13 C18 C17 -177.86(16) . . . . ?

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.055



####################################################################### 
# 
# 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_C5
_database_code_depnum_ccdc_archive 'CCDC 2370351'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Cl2 Cu N4 O2'
_chemical_formula_sum            'C18 H20 Cl2 Cu N4 O2'
_chemical_formula_weight         458.82

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'

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

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

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

_cell_length_a                   14.4376(6)
_cell_length_b                   8.0593(3)
_cell_length_c                   16.8258(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.442(4)
_cell_angle_gamma                90
_cell_volume                     1936.59(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    4716
_cell_measurement_theta_min      2.0050
_cell_measurement_theta_max      26.5380

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_F_000             940
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    1.425
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.55330
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_reflns_number            7702
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.911
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.911
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.911
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3853
_reflns_number_gt                3202
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+0.3983P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3853
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1210
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.57738(2) 0.55430(4) 0.30185(2) 0.02080(14) Uani 1 1 d . . . . .
Cl1 Cl 0.60177(5) 0.70106(9) 0.19538(4) 0.02584(19) Uani 1 1 d . . . . .
Cl2 Cl 0.46048(5) 0.73176(9) 0.34893(4) 0.02323(19) Uani 1 1 d . . . . .
N1 N 0.52888(16) 0.3469(3) 0.25007(14) 0.0198(5) Uani 1 1 d . . . . .
C2 C 0.52470(19) 0.2238(4) 0.30133(17) 0.0200(6) Uani 1 1 d . . . . .
N3 N 0.49084(17) 0.0815(3) 0.26665(15) 0.0233(6) Uani 1 1 d . . . . .
H3 H 0.482976 -0.013218 0.290781 0.028 Uiso 1 1 calc R U . . .
C4 C 0.4707(2) 0.1152(4) 0.18440(17) 0.0210(6) Uani 1 1 d . . . . .
C5 C 0.4325(2) 0.0158(4) 0.12124(19) 0.0260(7) Uani 1 1 d . . . . .
H5 H 0.415556 -0.096279 0.129111 0.031 Uiso 1 1 calc R U . . .
C6 C 0.4201(2) 0.0879(4) 0.0459(2) 0.0299(7) Uani 1 1 d . . . . .
H6 H 0.393581 0.024043 0.000815 0.036 Uiso 1 1 calc R U . . .
C7 C 0.4455(2) 0.2520(4) 0.03452(18) 0.0262(7) Uani 1 1 d . . . . .
H7 H 0.437451 0.296283 -0.018372 0.031 Uiso 1 1 calc R U . . .
C8 C 0.4821(2) 0.3521(4) 0.09819(18) 0.0243(7) Uani 1 1 d . . . . .
H8 H 0.497988 0.464784 0.090378 0.029 Uiso 1 1 calc R U . . .
C9 C 0.49480(19) 0.2801(4) 0.17444(17) 0.0199(6) Uani 1 1 d . . . . .
C10 C 0.5340(2) 0.1291(4) 0.44245(18) 0.0262(7) Uani 1 1 d . . . . .
H10A H 0.591894 0.101670 0.478085 0.039 Uiso 1 1 calc R U . . .
H10B H 0.506530 0.027556 0.416968 0.039 Uiso 1 1 calc R U . . .
H10C H 0.489529 0.180444 0.473778 0.039 Uiso 1 1 calc R U . . .
N10 N 0.55454(18) 0.2432(3) 0.38138(14) 0.0238(6) Uani 1 1 d . . . . .
N11 N 0.59130(17) 0.3997(3) 0.40013(15) 0.0214(5) Uani 1 1 d . . . . .
C12 C 0.6200(2) 0.4324(4) 0.47487(17) 0.0219(6) Uani 1 1 d . . . . .
H12 H 0.613459 0.349317 0.513698 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6614(2) 0.5890(4) 0.50227(18) 0.0222(6) Uani 1 1 d . . . . .
C14 C 0.6948(2) 0.7095(4) 0.45348(17) 0.0215(6) Uani 1 1 d . . . . .
O14 O 0.69258(13) 0.6764(3) 0.37170(11) 0.0209(4) Uani 1 1 d . . . . .
C141 C 0.7826(2) 0.6200(5) 0.3510(2) 0.0333(8) Uani 1 1 d . . . . .
H14A H 0.791526 0.502339 0.364818 0.050 Uiso 1 1 calc R U . . .
H14B H 0.833412 0.685079 0.381091 0.050 Uiso 1 1 calc R U . . .
H14C H 0.783114 0.634773 0.293250 0.050 Uiso 1 1 calc R U . . .
C15 C 0.7282(2) 0.8613(4) 0.48209(18) 0.0235(6) Uani 1 1 d . . . . .
C151 C 0.7593(2) 0.9902(4) 0.42648(19) 0.0300(7) Uani 1 1 d . . . . .
H15A H 0.825036 0.971331 0.420817 0.045 Uiso 1 1 calc R U . . .
H15B H 0.752379 1.101051 0.448848 0.045 Uiso 1 1 calc R U . . .
H15C H 0.720539 0.981967 0.373687 0.045 Uiso 1 1 calc R U . . .
C16 C 0.7325(2) 0.8909(4) 0.56575(19) 0.0247(7) Uani 1 1 d . . . . .
O16 O 0.76269(16) 1.0448(3) 0.58957(14) 0.0314(5) Uani 1 1 d . . . . .
C161 C 0.7733(2) 1.0825(5) 0.6737(2) 0.0339(8) Uani 1 1 d . . . . .
H16A H 0.794493 1.197415 0.682386 0.051 Uiso 1 1 calc R U . . .
H16B H 0.819545 1.007356 0.703055 0.051 Uiso 1 1 calc R U . . .
H16C H 0.712984 1.068366 0.693079 0.051 Uiso 1 1 calc R U . . .
C17 C 0.7052(2) 0.7711(4) 0.61653(18) 0.0266(7) Uani 1 1 d . . . . .
H17 H 0.710810 0.791358 0.672658 0.032 Uiso 1 1 calc R U . . .
C18 C 0.6698(2) 0.6227(4) 0.58521(18) 0.0251(7) Uani 1 1 d . . . . .
H18 H 0.650569 0.541255 0.620182 0.030 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 N1 1.966(3) . ?
Cu1 N11 2.057(2) . ?
Cu1 O14 2.131(2) . ?
Cu1 Cl1 2.2175(8) . ?
Cu1 Cl2 2.4318(8) . ?
N1 C2 1.322(4) . ?
N1 C9 1.403(4) . ?
C2 N3 1.345(4) . ?
C2 N10 1.362(4) . ?
N3 C4 1.398(4) . ?
N3 H3 0.8800 . ?
C4 C5 1.380(4) . ?
C4 C9 1.391(4) . ?
C5 C6 1.382(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.393(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.395(4) . ?
C8 H8 0.9500 . ?
C10 N10 1.442(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N10 N11 1.386(3) . ?
N11 C12 1.292(4) . ?
C12 C13 1.443(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.401(4) . ?
C13 C18 1.409(4) . ?
C14 C15 1.376(4) . ?
C14 O14 1.397(3) . ?
O14 C141 1.467(3) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C15 C16 1.420(4) . ?
C15 C151 1.510(4) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C16 O16 1.356(4) . ?
C16 C17 1.384(4) . ?
O16 C161 1.433(4) . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C17 C18 1.375(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N11 80.08(10) . . ?
N1 Cu1 O14 146.66(9) . . ?
N11 Cu1 O14 81.95(9) . . ?
N1 Cu1 Cl1 100.60(7) . . ?
N11 Cu1 Cl1 164.65(7) . . ?
O14 Cu1 Cl1 89.75(6) . . ?
N1 Cu1 Cl2 115.17(7) . . ?
N11 Cu1 Cl2 94.88(7) . . ?
O14 Cu1 Cl2 94.11(6) . . ?
Cl1 Cu1 Cl2 98.60(3) . . ?
C2 N1 C9 105.1(2) . . ?
C2 N1 Cu1 113.37(19) . . ?
C9 N1 Cu1 141.5(2) . . ?
N1 C2 N3 113.9(3) . . ?
N1 C2 N10 121.4(3) . . ?
N3 C2 N10 124.7(3) . . ?
C2 N3 C4 105.9(2) . . ?
C2 N3 H3 127.1 . . ?
C4 N3 H3 127.1 . . ?
C5 C4 C9 122.8(3) . . ?
C5 C4 N3 130.7(3) . . ?
C9 C4 N3 106.6(3) . . ?
C4 C5 C6 116.5(3) . . ?
C4 C5 H5 121.8 . . ?
C6 C5 H5 121.8 . . ?
C5 C6 C7 121.6(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.7(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C9 116.9(3) . . ?
C7 C8 H8 121.5 . . ?
C9 C8 H8 121.5 . . ?
C4 C9 C8 120.5(3) . . ?
C4 C9 N1 108.5(3) . . ?
C8 C9 N1 131.0(3) . . ?
N10 C10 H10A 109.5 . . ?
N10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N10 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2 N10 N11 112.6(2) . . ?
C2 N10 C10 124.2(3) . . ?
N11 N10 C10 122.0(2) . . ?
C12 N11 N10 117.7(2) . . ?
C12 N11 Cu1 129.7(2) . . ?
N10 N11 Cu1 112.28(18) . . ?
N11 C12 C13 123.2(3) . . ?
N11 C12 H12 118.4 . . ?
C13 C12 H12 118.4 . . ?
C14 C13 C18 117.4(3) . . ?
C14 C13 C12 125.5(3) . . ?
C18 C13 C12 117.1(3) . . ?
C15 C14 O14 118.0(3) . . ?
C15 C14 C13 123.0(3) . . ?
O14 C14 C13 119.0(3) . . ?
C14 O14 C141 113.6(2) . . ?
C14 O14 Cu1 122.29(16) . . ?
C141 O14 Cu1 111.91(18) . . ?
O14 C141 H14A 109.5 . . ?
O14 C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14 C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C14 C15 C16 117.3(3) . . ?
C14 C15 C151 121.1(3) . . ?
C16 C15 C151 121.7(3) . . ?
C15 C151 H15A 109.5 . . ?
C15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
C15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16 C16 C17 124.3(3) . . ?
O16 C16 C15 114.3(3) . . ?
C17 C16 C15 121.3(3) . . ?
C16 O16 C161 117.9(3) . . ?
O16 C161 H16A 109.5 . . ?
O16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C18 C17 C16 119.6(3) . . ?
C18 C17 H17 120.2 . . ?
C16 C17 H17 120.2 . . ?
C17 C18 C13 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C13 C18 H18 119.3 . . ?

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
C9 N1 C2 N3 -0.1(3) . . . . ?
Cu1 N1 C2 N3 179.45(19) . . . . ?
C9 N1 C2 N10 178.6(2) . . . . ?
Cu1 N1 C2 N10 -1.8(3) . . . . ?
N1 C2 N3 C4 -0.1(3) . . . . ?
N10 C2 N3 C4 -178.8(3) . . . . ?
C2 N3 C4 C5 -178.2(3) . . . . ?
C2 N3 C4 C9 0.3(3) . . . . ?
C9 C4 C5 C6 0.9(4) . . . . ?
N3 C4 C5 C6 179.1(3) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C5 C6 C7 C8 -1.7(5) . . . . ?
C6 C7 C8 C9 1.6(4) . . . . ?
C5 C4 C9 C8 -1.0(4) . . . . ?
N3 C4 C9 C8 -179.5(2) . . . . ?
C5 C4 C9 N1 178.2(3) . . . . ?
N3 C4 C9 N1 -0.3(3) . . . . ?
C7 C8 C9 C4 -0.3(4) . . . . ?
C7 C8 C9 N1 -179.3(3) . . . . ?
C2 N1 C9 C4 0.3(3) . . . . ?
Cu1 N1 C9 C4 -179.1(2) . . . . ?
C2 N1 C9 C8 179.4(3) . . . . ?
Cu1 N1 C9 C8 0.0(5) . . . . ?
N1 C2 N10 N11 -2.3(4) . . . . ?
N3 C2 N10 N11 176.3(3) . . . . ?
N1 C2 N10 C10 165.9(3) . . . . ?
N3 C2 N10 C10 -15.5(4) . . . . ?
C2 N10 N11 C12 178.6(3) . . . . ?
C10 N10 N11 C12 10.1(4) . . . . ?
C2 N10 N11 Cu1 5.0(3) . . . . ?
C10 N10 N11 Cu1 -163.5(2) . . . . ?
N10 N11 C12 C13 178.6(3) . . . . ?
Cu1 N11 C12 C13 -9.0(4) . . . . ?
N11 C12 C13 C14 -14.8(5) . . . . ?
N11 C12 C13 C18 165.8(3) . . . . ?
C18 C13 C14 C15 -4.9(5) . . . . ?
C12 C13 C14 C15 175.7(3) . . . . ?
C18 C13 C14 O14 176.4(3) . . . . ?
C12 C13 C14 O14 -3.0(5) . . . . ?
C15 C14 O14 C141 82.4(3) . . . . ?
C13 C14 O14 C141 -98.8(3) . . . . ?
C15 C14 O14 Cu1 -138.4(2) . . . . ?
C13 C14 O14 Cu1 40.4(3) . . . . ?
O14 C14 C15 C16 -178.2(2) . . . . ?
C13 C14 C15 C16 3.0(5) . . . . ?
O14 C14 C15 C151 1.6(4) . . . . ?
C13 C14 C15 C151 -177.1(3) . . . . ?
C14 C15 C16 O16 -177.6(3) . . . . ?
C151 C15 C16 O16 2.6(4) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C151 C15 C16 C17 -179.1(3) . . . . ?
C17 C16 O16 C161 4.6(4) . . . . ?
C15 C16 O16 C161 -177.1(3) . . . . ?
O16 C16 C17 C18 175.7(3) . . . . ?
C15 C16 C17 C18 -2.5(5) . . . . ?
C16 C17 C18 C13 0.6(5) . . . . ?
C14 C13 C18 C17 3.0(5) . . . . ?
C12 C13 C18 C17 -177.6(3) . . . . ?

_refine_diff_density_max         0.671
_refine_diff_density_min         -1.141
_refine_diff_density_rms         0.102



####################################################################### 
# 
# 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_C4
_database_code_depnum_ccdc_archive 'CCDC 2370350'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 Cl2 Cu N4 O'
_chemical_formula_sum            'C16 H16 Cl2 Cu N4 O'
_chemical_formula_weight         414.77

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2961(7)
_cell_length_b                   13.6909(5)
_cell_length_c                   14.6952(11)
_cell_angle_alpha                89.989(5)
_cell_angle_beta                 88.450(7)
_cell_angle_gamma                82.033(6)
_cell_volume                     1652.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    4737
_cell_measurement_theta_min      2.9890
_cell_measurement_theta_max      75.8260

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.667
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    4.937
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.51843
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.56a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            7542
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.008
_diffrn_reflns_theta_max         67.494
_diffrn_reflns_theta_full        67.494
_diffrn_measured_fraction_theta_max 0.843
_diffrn_measured_fraction_theta_full 0.843
_diffrn_reflns_Laue_measured_fraction_max 0.843
_diffrn_reflns_Laue_measured_fraction_full 0.843
_diffrn_reflns_point_group_measured_fraction_max 0.843
_diffrn_reflns_point_group_measured_fraction_full 0.843
_reflns_number_total             4997
_reflns_number_gt                4500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_audit_creation_method           'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.56a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0950P)²+40.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4997
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1373
_refine_ls_R_factor_gt           0.1322
_refine_ls_wR_factor_ref         0.3031
_refine_ls_wR_factor_gt          0.3014
_refine_ls_goodness_of_fit_ref   1.002
_refine_ls_restrained_S_all      1.002
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1A Cu 0.6351(2) 0.66396(12) 0.86379(13) 0.0460(5) Uani 1 1 d . . . . .
Cl1A Cl 0.7702(5) 0.6597(2) 0.7315(2) 0.0605(9) Uani 1 1 d . . . . .
Cl2A Cl 0.3766(4) 0.6873(2) 0.8068(2) 0.0509(8) Uani 1 1 d . . . . .
N1A N 0.7637(12) 0.5515(7) 0.9255(8) 0.045(2) Uani 1 1 d . . . . .
C2A C 0.7033(14) 0.5371(8) 1.0063(9) 0.044(3) Uani 1 1 d . . . . .
N3A N 0.7619(13) 0.4469(7) 1.0421(8) 0.051(3) Uani 1 1 d . . . . .
H3A H 0.734564 0.422268 1.094650 0.061 Uiso 1 1 calc R U . . .
C4A C 0.8746(15) 0.4028(9) 0.9766(11) 0.053(3) Uani 1 1 d . . . . .
C5A C 0.9734(19) 0.3090(10) 0.9769(14) 0.070(5) Uani 1 1 d . . . . .
H5A H 0.970964 0.263433 1.025518 0.084 Uiso 1 1 calc R U . . .
C6A C 1.0728(19) 0.2903(13) 0.9005(17) 0.089(7) Uani 1 1 d . . . . .
H6A H 1.143391 0.229461 0.897303 0.107 Uiso 1 1 calc R U . . .
C7A C 1.0758(17) 0.3550(12) 0.8280(13) 0.069(4) Uani 1 1 d . . . . .
H7A H 1.147103 0.337248 0.777191 0.082 Uiso 1 1 calc R U . . .
C8A C 0.9767(16) 0.4447(10) 0.8288(11) 0.060(4) Uani 1 1 d . . . . .
H8A H 0.977647 0.488741 0.778836 0.072 Uiso 1 1 calc R U . . .
C9A C 0.8761(14) 0.4686(9) 0.9042(11) 0.052(3) Uani 1 1 d . . . . .
C10A C 0.5304(15) 0.5994(8) 1.1415(9) 0.046(3) Uani 1 1 d . . . . .
H10A H 0.575594 0.650030 1.175960 0.069 Uiso 1 1 calc R U . . .
H10B H 0.568943 0.534227 1.166431 0.069 Uiso 1 1 calc R U . . .
H10C H 0.411215 0.611605 1.146047 0.069 Uiso 1 1 calc R U . . .
N10A N 0.5820(13) 0.6029(7) 1.0481(7) 0.044(2) Uani 1 1 d . . . . .
N11A N 0.5516(13) 0.6881(7) 0.9953(7) 0.046(2) Uani 1 1 d . . . . .
C12A C 0.4541(14) 0.7607(8) 1.0285(9) 0.044(3) Uani 1 1 d . . . . .
H12A H 0.407786 0.755422 1.087778 0.053 Uiso 1 1 calc R U . . .
C13A C 0.4117(16) 0.8534(8) 0.9757(9) 0.047(3) Uani 1 1 d . . . . .
O14A O 0.6679(10) 0.8328(6) 0.8989(6) 0.048(2) Uani 1 1 d . . . . .
C14A C 0.5191(14) 0.8878(8) 0.9112(9) 0.044(3) Uani 1 1 d . . . . .
C141 C 0.7889(15) 0.8742(9) 0.8444(10) 0.054(3) Uani 1 1 d . . . . .
H14A H 0.894830 0.833354 0.850212 0.081 Uiso 1 1 calc R U . . .
H14B H 0.796027 0.941297 0.865554 0.081 Uiso 1 1 calc R U . . .
H14C H 0.757878 0.876049 0.780487 0.081 Uiso 1 1 calc R U . . .
C15A C 0.4710(16) 0.9751(8) 0.8671(9) 0.049(3) Uani 1 1 d . . . . .
H15A H 0.545847 1.001736 0.827391 0.058 Uiso 1 1 calc R U . . .
C16A C 0.3160(17) 1.0244(9) 0.8797(10) 0.054(3) Uani 1 1 d . . . . .
H16A H 0.281168 1.081748 0.845125 0.065 Uiso 1 1 calc R U . . .
C17A C 0.2104(18) 0.9898(9) 0.9433(11) 0.059(4) Uani 1 1 d . . . . .
H17A H 0.103975 1.024625 0.952824 0.070 Uiso 1 1 calc R U . . .
C18A C 0.2587(15) 0.9053(8) 0.9929(9) 0.047(3) Uani 1 1 d . . . . .
H18A H 0.187860 0.883385 1.038002 0.057 Uiso 1 1 calc R U . . .
Cu1B Cu 0.3532(2) 0.83770(12) 0.36958(13) 0.0450(5) Uani 1 1 d . . . . .
Cl1B Cl 0.6065(4) 0.8141(2) 0.2981(2) 0.0483(7) Uani 1 1 d . . . . .
Cl2B Cl 0.2070(4) 0.8441(2) 0.2458(2) 0.0601(9) Uani 1 1 d . . . . .
N1B N 0.2401(12) 0.9524(6) 0.4377(7) 0.041(2) Uani 1 1 d . . . . .
C2B C 0.3021(14) 0.9641(8) 0.5175(9) 0.041(3) Uani 1 1 d . . . . .
N3B N 0.2493(12) 1.0523(7) 0.5569(8) 0.045(2) Uani 1 1 d . . . . .
H3B H 0.278148 1.073993 0.609542 0.054 Uiso 1 1 calc R U . . .
C4B C 0.1403(14) 1.1013(9) 0.4970(11) 0.051(3) Uani 1 1 d . . . . .
C5B C 0.0466(16) 1.1942(9) 0.5048(12) 0.059(4) Uani 1 1 d . . . . .
H5B H 0.051388 1.235722 0.556209 0.071 Uiso 1 1 calc R U . . .
C6B C -0.0524(18) 1.2213(10) 0.4334(13) 0.070(5) Uani 1 1 d . . . . .
H6B H -0.118165 1.283937 0.435675 0.084 Uiso 1 1 calc R U . . .
C7B C -0.0614(17) 1.1618(11) 0.3579(12) 0.064(4) Uani 1 1 d . . . . .
H7B H -0.130627 1.185006 0.309751 0.077 Uiso 1 1 calc R U . . .
C8B C 0.0301(15) 1.0678(10) 0.3513(11) 0.056(3) Uani 1 1 d . . . . .
H8B H 0.022589 1.025613 0.300734 0.067 Uiso 1 1 calc R U . . .
C9B C 0.1328(14) 1.0395(9) 0.4232(10) 0.048(3) Uani 1 1 d . . . . .
C10B C 0.4683(16) 0.8949(9) 0.6434(9) 0.049(3) Uani 1 1 d . . . . .
H10D H 0.437238 0.837386 0.675597 0.074 Uiso 1 1 calc R U . . .
H10E H 0.415649 0.955341 0.673495 0.074 Uiso 1 1 calc R U . . .
H10F H 0.586776 0.892956 0.644219 0.074 Uiso 1 1 calc R U . . .
N10B N 0.4176(12) 0.8936(7) 0.5513(7) 0.043(2) Uani 1 1 d . . . . .
N11B N 0.4482(12) 0.8119(7) 0.4955(7) 0.045(2) Uani 1 1 d . . . . .
C12B C 0.5446(14) 0.7380(8) 0.5231(9) 0.042(3) Uani 1 1 d . . . . .
H12B H 0.589231 0.741770 0.581629 0.051 Uiso 1 1 calc R U . . .
C13B C 0.5911(14) 0.6473(8) 0.4696(9) 0.042(3) Uani 1 1 d . . . . .
O14B O 0.3387(9) 0.6645(5) 0.3981(6) 0.0437(19) Uani 1 1 d . . . . .
C14B C 0.4875(14) 0.6106(8) 0.4086(8) 0.041(3) Uani 1 1 d . . . . .
C142 C 0.2240(14) 0.6203(9) 0.3453(9) 0.047(3) Uani 1 1 d . . . . .
H14D H 0.263125 0.613903 0.281813 0.070 Uiso 1 1 calc R U . . .
H14E H 0.118031 0.662026 0.348540 0.070 Uiso 1 1 calc R U . . .
H14F H 0.212843 0.554878 0.369756 0.070 Uiso 1 1 calc R U . . .
C15B C 0.5408(15) 0.5204(8) 0.3637(9) 0.045(3) Uani 1 1 d . . . . .
H15B H 0.468803 0.491690 0.325948 0.054 Uiso 1 1 calc R U . . .
C16B C 0.6957(16) 0.4745(8) 0.3746(9) 0.050(3) Uani 1 1 d . . . . .
H16B H 0.733212 0.416873 0.339879 0.061 Uiso 1 1 calc R U . . .
C17B C 0.7983(16) 0.5092(8) 0.4341(9) 0.048(3) Uani 1 1 d . . . . .
H17B H 0.904999 0.475272 0.441440 0.058 Uiso 1 1 calc R U . . .
C18B C 0.7448(14) 0.5952(8) 0.4842(9) 0.044(3) Uani 1 1 d . . . . .
H18B H 0.813122 0.618043 0.528018 0.053 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
Cu1A N1A 1.982(9) . ?
Cu1A N11A 2.047(11) . ?
Cu1A Cl1A 2.215(4) . ?
Cu1A Cl2A 2.305(4) . ?
Cu1A O14A 2.421(8) . ?
N1A C2A 1.301(16) . ?
N1A C9A 1.395(15) . ?
C2A N3A 1.373(15) . ?
C2A N10A 1.384(15) . ?
N3A C4A 1.400(18) . ?
N3A H3A 0.8800 . ?
C4A C9A 1.40(2) . ?
C4A C5A 1.424(18) . ?
C5A C6A 1.38(3) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.39(3) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.38(2) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.38(2) . ?
C8A H8A 0.9500 . ?
C10A N10A 1.429(16) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
N10A N11A 1.399(13) . ?
N11A C12A 1.278(15) . ?
C12A C13A 1.493(17) . ?
C12A H12A 0.9500 . ?
C13A C18A 1.383(17) . ?
C13A C14A 1.408(17) . ?
O14A C14A 1.362(14) . ?
O14A C141 1.443(14) . ?
C14A C15A 1.375(17) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C15A C16A 1.375(18) . ?
C15A H15A 0.9500 . ?
C16A C17A 1.391(19) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.385(18) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
Cu1B N1B 1.973(9) . ?
Cu1B N11B 2.042(11) . ?
Cu1B Cl2B 2.208(4) . ?
Cu1B Cl1B 2.305(3) . ?
Cu1B O14B 2.427(7) . ?
N1B C2B 1.311(16) . ?
N1B C9B 1.405(15) . ?
C2B N3B 1.351(14) . ?
C2B N10B 1.366(15) . ?
N3B C4B 1.385(17) . ?
N3B H3B 0.8800 . ?
C4B C9B 1.38(2) . ?
C4B C5B 1.399(17) . ?
C5B C6B 1.37(2) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.39(2) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.40(2) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.396(19) . ?
C8B H8B 0.9500 . ?
C10B N10B 1.428(16) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
N10B N11B 1.378(13) . ?
N11B C12B 1.273(15) . ?
C12B C13B 1.470(15) . ?
C12B H12B 0.9500 . ?
C13B C18B 1.394(16) . ?
C13B C14B 1.399(17) . ?
O14B C14B 1.360(14) . ?
O14B C142 1.439(14) . ?
C14B C15B 1.409(16) . ?
C142 H14D 0.9800 . ?
C142 H14E 0.9800 . ?
C142 H14F 0.9800 . ?
C15B C16B 1.364(18) . ?
C15B H15B 0.9500 . ?
C16B C17B 1.367(19) . ?
C16B H16B 0.9500 . ?
C17B C18B 1.402(17) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1A Cu1A N11A 79.5(4) . . ?
N1A Cu1A Cl1A 99.9(3) . . ?
N11A Cu1A Cl1A 166.2(3) . . ?
N1A Cu1A Cl2A 132.9(3) . . ?
N11A Cu1A Cl2A 93.1(3) . . ?
Cl1A Cu1A Cl2A 97.20(15) . . ?
N1A Cu1A O14A 121.3(4) . . ?
N11A Cu1A O14A 74.0(3) . . ?
Cl1A Cu1A O14A 95.1(2) . . ?
Cl2A Cu1A O14A 100.2(2) . . ?
C2A N1A C9A 107.0(10) . . ?
C2A N1A Cu1A 111.5(8) . . ?
C9A N1A Cu1A 139.5(10) . . ?
N1A C2A N3A 113.2(11) . . ?
N1A C2A N10A 123.0(10) . . ?
N3A C2A N10A 123.6(12) . . ?
C2A N3A C4A 104.9(11) . . ?
C2A N3A H3A 127.5 . . ?
C4A N3A H3A 127.5 . . ?
C9A C4A N3A 107.3(10) . . ?
C9A C4A C5A 122.7(15) . . ?
N3A C4A C5A 130.0(15) . . ?
C6A C5A C4A 114.1(16) . . ?
C6A C5A H5A 123.0 . . ?
C4A C5A H5A 123.0 . . ?
C5A C6A C7A 123.9(14) . . ?
C5A C6A H6A 118.0 . . ?
C7A C6A H6A 118.0 . . ?
C8A C7A C6A 120.8(16) . . ?
C8A C7A H7A 119.6 . . ?
C6A C7A H7A 119.6 . . ?
C9A C8A C7A 118.1(16) . . ?
C9A C8A H8A 121.0 . . ?
C7A C8A H8A 121.0 . . ?
C8A C9A N1A 132.0(14) . . ?
C8A C9A C4A 120.4(12) . . ?
N1A C9A C4A 107.6(12) . . ?
N10A C10A H10A 109.5 . . ?
N10A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N10A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C2A N10A N11A 109.6(10) . . ?
C2A N10A C10A 125.2(10) . . ?
N11A N10A C10A 122.7(9) . . ?
C12A N11A N10A 117.8(11) . . ?
C12A N11A Cu1A 129.0(9) . . ?
N10A N11A Cu1A 111.7(7) . . ?
N11A C12A C13A 121.3(12) . . ?
N11A C12A H12A 119.4 . . ?
C13A C12A H12A 119.4 . . ?
C18A C13A C14A 120.6(11) . . ?
C18A C13A C12A 116.5(11) . . ?
C14A C13A C12A 122.9(11) . . ?
C14A O14A C141 117.8(9) . . ?
C14A O14A Cu1A 109.8(6) . . ?
C141 O14A Cu1A 115.8(7) . . ?
O14A C14A C15A 124.1(11) . . ?
O14A C14A C13A 116.9(10) . . ?
C15A C14A C13A 119.0(12) . . ?
O14A C141 H14A 109.5 . . ?
O14A C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14A C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C16A C15A C14A 120.9(12) . . ?
C16A C15A H15A 119.6 . . ?
C14A C15A H15A 119.6 . . ?
C15A C16A C17A 119.6(12) . . ?
C15A C16A H16A 120.2 . . ?
C17A C16A H16A 120.2 . . ?
C18A C17A C16A 120.7(13) . . ?
C18A C17A H17A 119.6 . . ?
C16A C17A H17A 119.6 . . ?
C13A C18A C17A 118.9(12) . . ?
C13A C18A H18A 120.5 . . ?
C17A C18A H18A 120.5 . . ?
N1B Cu1B N11B 79.2(4) . . ?
N1B Cu1B Cl2B 100.7(3) . . ?
N11B Cu1B Cl2B 166.3(3) . . ?
N1B Cu1B Cl1B 130.4(3) . . ?
N11B Cu1B Cl1B 92.8(3) . . ?
Cl2B Cu1B Cl1B 97.40(15) . . ?
N1B Cu1B O14B 127.6(3) . . ?
N11B Cu1B O14B 75.2(3) . . ?
Cl2B Cu1B O14B 94.6(2) . . ?
Cl1B Cu1B O14B 96.0(2) . . ?
C2B N1B C9B 105.2(10) . . ?
C2B N1B Cu1B 113.1(8) . . ?
C9B N1B Cu1B 140.1(9) . . ?
N1B C2B N3B 113.8(11) . . ?
N1B C2B N10B 120.6(10) . . ?
N3B C2B N10B 125.4(12) . . ?
C2B N3B C4B 105.6(11) . . ?
C2B N3B H3B 127.2 . . ?
C4B N3B H3B 127.2 . . ?
C9B C4B N3B 107.3(10) . . ?
C9B C4B C5B 122.8(14) . . ?
N3B C4B C5B 129.8(14) . . ?
C6B C5B C4B 115.5(16) . . ?
C6B C5B H5B 122.3 . . ?
C4B C5B H5B 122.3 . . ?
C5B C6B C7B 123.1(14) . . ?
C5B C6B H6B 118.4 . . ?
C7B C6B H6B 118.4 . . ?
C6B C7B C8B 121.1(15) . . ?
C6B C7B H7B 119.4 . . ?
C8B C7B H7B 119.4 . . ?
C9B C8B C7B 116.4(15) . . ?
C9B C8B H8B 121.8 . . ?
C7B C8B H8B 121.8 . . ?
C4B C9B C8B 121.0(12) . . ?
C4B C9B N1B 108.0(12) . . ?
C8B C9B N1B 131.0(13) . . ?
N10B C10B H10D 109.5 . . ?
N10B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N10B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C2B N10B N11B 112.3(10) . . ?
C2B N10B C10B 122.4(10) . . ?
N11B N10B C10B 123.6(10) . . ?
C12B N11B N10B 118.1(11) . . ?
C12B N11B Cu1B 129.0(9) . . ?
N10B N11B Cu1B 112.2(7) . . ?
N11B C12B C13B 123.8(12) . . ?
N11B C12B H12B 118.1 . . ?
C13B C12B H12B 118.1 . . ?
C18B C13B C14B 119.8(11) . . ?
C18B C13B C12B 116.8(11) . . ?
C14B C13B C12B 123.3(11) . . ?
C14B O14B C142 116.8(9) . . ?
C14B O14B Cu1B 112.9(6) . . ?
C142 O14B Cu1B 116.1(7) . . ?
O14B C14B C13B 116.8(10) . . ?
O14B C14B C15B 124.3(10) . . ?
C13B C14B C15B 118.9(11) . . ?
O14B C142 H14D 109.5 . . ?
O14B C142 H14E 109.5 . . ?
H14D C142 H14E 109.5 . . ?
O14B C142 H14F 109.5 . . ?
H14D C142 H14F 109.5 . . ?
H14E C142 H14F 109.5 . . ?
C16B C15B C14B 120.0(11) . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C16B C17B 121.7(11) . . ?
C15B C16B H16B 119.2 . . ?
C17B C16B H16B 119.2 . . ?
C16B C17B C18B 119.5(12) . . ?
C16B C17B H17B 120.3 . . ?
C18B C17B H17B 120.3 . . ?
C13B C18B C17B 119.9(11) . . ?
C13B C18B H18B 120.1 . . ?
C17B C18B H18B 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9A N1A C2A N3A -2.4(14) . . . . ?
Cu1A N1A C2A N3A 164.7(8) . . . . ?
C9A N1A C2A N10A -177.2(11) . . . . ?
Cu1A N1A C2A N10A -10.1(15) . . . . ?
N1A C2A N3A C4A 2.0(14) . . . . ?
N10A C2A N3A C4A 176.7(12) . . . . ?
C2A N3A C4A C9A -0.8(13) . . . . ?
C2A N3A C4A C5A 179.8(13) . . . . ?
C9A C4A C5A C6A 1(2) . . . . ?
N3A C4A C5A C6A -179.2(14) . . . . ?
C4A C5A C6A C7A -1(2) . . . . ?
C5A C6A C7A C8A 0(2) . . . . ?
C6A C7A C8A C9A 1(2) . . . . ?
C7A C8A C9A N1A -179.8(13) . . . . ?
C7A C8A C9A C4A -0.7(19) . . . . ?
C2A N1A C9A C8A -179.0(14) . . . . ?
Cu1A N1A C9A C8A 20(2) . . . . ?
C2A N1A C9A C4A 1.8(13) . . . . ?
Cu1A N1A C9A C4A -159.6(10) . . . . ?
N3A C4A C9A C8A -179.9(12) . . . . ?
C5A C4A C9A C8A 0(2) . . . . ?
N3A C4A C9A N1A -0.6(13) . . . . ?
C5A C4A C9A N1A 178.9(12) . . . . ?
N1A C2A N10A N11A -6.6(16) . . . . ?
N3A C2A N10A N11A 179.1(10) . . . . ?
N1A C2A N10A C10A -169.0(11) . . . . ?
N3A C2A N10A C10A 16.7(19) . . . . ?
C2A N10A N11A C12A -173.2(11) . . . . ?
C10A N10A N11A C12A -10.3(16) . . . . ?
C2A N10A N11A Cu1A 19.4(12) . . . . ?
C10A N10A N11A Cu1A -177.7(9) . . . . ?
N10A N11A C12A C13A -178.4(10) . . . . ?
Cu1A N11A C12A C13A -13.5(17) . . . . ?
N11A C12A C13A C18A 149.9(12) . . . . ?
N11A C12A C13A C14A -29.9(18) . . . . ?
C141 O14A C14A C15A 7.6(17) . . . . ?
Cu1A O14A C14A C15A -127.9(11) . . . . ?
C141 O14A C14A C13A -170.3(11) . . . . ?
Cu1A O14A C14A C13A 54.2(12) . . . . ?
C18A C13A C14A O14A 179.5(11) . . . . ?
C12A C13A C14A O14A -0.7(17) . . . . ?
C18A C13A C14A C15A 1.5(18) . . . . ?
C12A C13A C14A C15A -178.7(12) . . . . ?
O14A C14A C15A C16A 176.9(11) . . . . ?
C13A C14A C15A C16A -5.3(18) . . . . ?
C14A C15A C16A C17A 5(2) . . . . ?
C15A C16A C17A C18A -1(2) . . . . ?
C14A C13A C18A C17A 2.3(19) . . . . ?
C12A C13A C18A C17A -177.5(12) . . . . ?
C16A C17A C18A C13A -3(2) . . . . ?
C9B N1B C2B N3B -1.6(13) . . . . ?
Cu1B N1B C2B N3B 167.1(7) . . . . ?
C9B N1B C2B N10B -177.4(10) . . . . ?
Cu1B N1B C2B N10B -8.6(13) . . . . ?
N1B C2B N3B C4B 1.2(13) . . . . ?
N10B C2B N3B C4B 176.7(11) . . . . ?
C2B N3B C4B C9B -0.2(12) . . . . ?
C2B N3B C4B C5B 178.2(12) . . . . ?
C9B C4B C5B C6B -0.9(19) . . . . ?
N3B C4B C5B C6B -179.1(12) . . . . ?
C4B C5B C6B C7B 0(2) . . . . ?
C5B C6B C7B C8B 1(2) . . . . ?
C6B C7B C8B C9B -1.8(19) . . . . ?
N3B C4B C9B C8B 178.8(10) . . . . ?
C5B C4B C9B C8B 0.3(19) . . . . ?
N3B C4B C9B N1B -0.7(13) . . . . ?
C5B C4B C9B N1B -179.2(11) . . . . ?
C7B C8B C9B C4B 1.1(18) . . . . ?
C7B C8B C9B N1B -179.5(12) . . . . ?
C2B N1B C9B C4B 1.4(12) . . . . ?
Cu1B N1B C9B C4B -162.4(9) . . . . ?
C2B N1B C9B C8B -178.1(12) . . . . ?
Cu1B N1B C9B C8B 18(2) . . . . ?
N1B C2B N10B N11B -3.8(15) . . . . ?
N3B C2B N10B N11B -179.0(10) . . . . ?
N1B C2B N10B C10B -169.2(10) . . . . ?
N3B C2B N10B C10B 15.6(18) . . . . ?
C2B N10B N11B C12B -174.8(10) . . . . ?
C10B N10B N11B C12B -9.6(16) . . . . ?
C2B N10B N11B Cu1B 13.7(11) . . . . ?
C10B N10B N11B Cu1B 178.9(9) . . . . ?
N10B N11B C12B C13B -178.4(10) . . . . ?
Cu1B N11B C12B C13B -8.6(17) . . . . ?
N11B C12B C13B C18B 150.3(12) . . . . ?
N11B C12B C13B C14B -31.8(18) . . . . ?
C142 O14B C14B C13B -171.7(10) . . . . ?
Cu1B O14B C14B C13B 49.8(12) . . . . ?
C142 O14B C14B C15B 6.9(16) . . . . ?
Cu1B O14B C14B C15B -131.6(10) . . . . ?
C18B C13B C14B O14B 179.4(10) . . . . ?
C12B C13B C14B O14B 1.6(17) . . . . ?
C18B C13B C14B C15B 0.8(17) . . . . ?
C12B C13B C14B C15B -177.0(11) . . . . ?
O14B C14B C15B C16B 176.3(11) . . . . ?
C13B C14B C15B C16B -5.2(18) . . . . ?
C14B C15B C16B C17B 5.5(19) . . . . ?
C15B C16B C17B C18B -1(2) . . . . ?
C14B C13B C18B C17B 3.4(18) . . . . ?
C12B C13B C18B C17B -178.6(11) . . . . ?
C16B C17B C18B C13B -3.3(18) . . . . ?

_refine_diff_density_max         2.924
_refine_diff_density_min         -1.041
_refine_diff_density_rms         0.232



####################################################################### 
# 
# 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_C2
_database_code_depnum_ccdc_archive 'CCDC 2336938'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H17 Cl Cu N4 O3'
_chemical_formula_weight         424.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   18.8457(3)
_cell_length_b                   6.69128(6)
_cell_length_c                   13.29018(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1675.91(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    125(1)
_cell_measurement_reflns_used    20515
_cell_measurement_theta_min      3.3070
_cell_measurement_theta_max      76.1740

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.682
_exptl_crystal_F_000             868
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.545
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.27584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            23536
_diffrn_reflns_av_unetI/netI     0.0165
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         5.756
_diffrn_reflns_theta_max         76.601
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3492
_reflns_number_gt                3488
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.999

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

_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.5509P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1639 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     238
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0258
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.44945(2) 0.28530(5) 0.46842(3) 0.01494(13) Uani 1 1 d . . . . .
Cl1 Cl 0.39059(3) 0.19007(9) 0.32828(5) 0.01887(16) Uani 1 1 d . . . . .
N1 N 0.52437(11) 0.0829(3) 0.46514(18) 0.0158(4) Uani 1 1 d . . . . .
C2 C 0.58030(14) 0.1345(4) 0.52109(19) 0.0162(5) Uani 1 1 d . . . . .
N3 N 0.63432(12) 0.0022(3) 0.51496(18) 0.0170(5) Uani 1 1 d . . . . .
H3 H 0.675723 0.010751 0.545281 0.020 Uiso 1 1 calc R U . . .
C4 C 0.61169(14) -0.1500(5) 0.4514(2) 0.0179(5) Uani 1 1 d . . . . .
C5 C 0.64485(15) -0.3262(4) 0.4203(2) 0.0185(5) Uani 1 1 d . . . . .
H5 H 0.692165 -0.357476 0.439302 0.022 Uiso 1 1 calc R U . . .
C6 C 0.60495(15) -0.4527(4) 0.3604(2) 0.0197(5) Uani 1 1 d . . . . .
H6 H 0.625656 -0.573195 0.336651 0.024 Uiso 1 1 calc R U . . .
C7 C 0.53455(16) -0.4073(4) 0.3339(2) 0.0198(5) Uani 1 1 d . . . . .
H7 H 0.508202 -0.500827 0.295225 0.024 Uiso 1 1 calc R U . . .
C8 C 0.50249(16) -0.2294(4) 0.3627(2) 0.0176(5) Uani 1 1 d . . . . .
H8 H 0.455310 -0.197940 0.343088 0.021 Uiso 1 1 calc R U . . .
C9 C 0.54231(14) -0.0997(4) 0.4212(2) 0.0165(5) Uani 1 1 d . . . . .
N10 N 0.57991(14) 0.3012(4) 0.5781(2) 0.0189(5) Uani 1 1 d . . . . .
N11 N 0.51736(12) 0.4084(4) 0.56682(18) 0.0158(4) Uani 1 1 d . . . . .
C12 C 0.51063(14) 0.5805(4) 0.6104(2) 0.0163(5) Uani 1 1 d . . . . .
H12 H 0.550207 0.632047 0.646242 0.020 Uiso 1 1 calc R U . . .
C13 C 0.44704(15) 0.6975(4) 0.6078(2) 0.0169(6) Uani 1 1 d . . . . .
O14 O 0.37901(10) 0.4747(3) 0.50075(16) 0.0190(4) Uani 1 1 d . . . . .
C14 C 0.38527(14) 0.6397(5) 0.55278(19) 0.0156(5) Uani 1 1 d . . . . .
C15 C 0.32679(16) 0.7712(4) 0.5556(2) 0.0169(5) Uani 1 1 d . . . . .
O15 O 0.26543(11) 0.7288(3) 0.50241(16) 0.0183(4) Uani 1 1 d . . . . .
C16 C 0.32792(14) 0.9452(4) 0.6133(2) 0.0182(5) Uani 1 1 d . . . . .
O16 O 0.26647(10) 1.0539(3) 0.61199(17) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.38829(15) 0.9994(5) 0.6686(2) 0.0200(6) Uani 1 1 d . . . . .
H17 H 0.388939 1.118023 0.707922 0.024 Uiso 1 1 calc R U . . .
C18 C 0.44664(14) 0.8757(5) 0.6643(2) 0.0176(6) Uani 1 1 d . . . . .
H18 H 0.488078 0.911835 0.700701 0.021 Uiso 1 1 calc R U . . .
C101 C 0.63325(16) 0.3414(5) 0.6539(2) 0.0235(6) Uani 1 1 d . . . . .
H10A H 0.670888 0.424386 0.624846 0.035 Uiso 1 1 calc R U . . .
H10B H 0.653525 0.215047 0.677619 0.035 Uiso 1 1 calc R U . . .
H10C H 0.611442 0.412170 0.710613 0.035 Uiso 1 1 calc R U . . .
C151 C 0.27592(17) 0.7367(5) 0.3951(3) 0.0241(6) Uani 1 1 d . . . . .
H15A H 0.229903 0.750750 0.361506 0.036 Uiso 1 1 calc R U . . .
H15B H 0.298992 0.613416 0.372494 0.036 Uiso 1 1 calc R U . . .
H15C H 0.305998 0.851483 0.378362 0.036 Uiso 1 1 calc R U . . .
C161 C 0.26391(17) 1.2319(5) 0.6718(3) 0.0254(7) Uani 1 1 d . . . . .
H16A H 0.296448 1.331564 0.643636 0.038 Uiso 1 1 calc R U . . .
H16B H 0.278050 1.200549 0.740940 0.038 Uiso 1 1 calc R U . . .
H16C H 0.215497 1.285311 0.671581 0.038 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 O14 1.885(2) . ?
Cu1 N1 1.957(2) . ?
Cu1 N11 2.007(2) . ?
Cu1 Cl1 2.2595(7) . ?
N1 C2 1.335(4) . ?
N1 C9 1.396(4) . ?
C2 N10 1.349(4) . ?
C2 N3 1.351(4) . ?
N3 C4 1.390(4) . ?
N3 H3 0.8800 . ?
C4 C5 1.397(4) . ?
C4 C9 1.408(4) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.386(4) . ?
C8 H8 0.9500 . ?
N10 N11 1.388(3) . ?
N10 C101 1.448(4) . ?
N11 C12 1.295(4) . ?
C12 C13 1.432(4) . ?
C12 H12 0.9500 . ?
C13 C18 1.409(4) . ?
C13 C14 1.428(4) . ?
O14 C14 1.308(4) . ?
C14 C15 1.411(4) . ?
C15 O15 1.384(4) . ?
C15 C16 1.395(4) . ?
O15 C151 1.441(4) . ?
C16 O16 1.368(3) . ?
C16 C17 1.402(4) . ?
O16 C161 1.432(4) . ?
C17 C18 1.377(4) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O14 Cu1 N1 168.09(10) . . ?
O14 Cu1 N11 91.41(9) . . ?
N1 Cu1 N11 80.70(9) . . ?
O14 Cu1 Cl1 91.82(6) . . ?
N1 Cu1 Cl1 98.09(7) . . ?
N11 Cu1 Cl1 165.03(7) . . ?
C2 N1 C9 105.5(2) . . ?
C2 N1 Cu1 112.24(18) . . ?
C9 N1 Cu1 142.17(18) . . ?
N1 C2 N10 121.5(3) . . ?
N1 C2 N3 113.1(2) . . ?
N10 C2 N3 125.4(3) . . ?
C2 N3 C4 106.6(2) . . ?
C2 N3 H3 126.7 . . ?
C4 N3 H3 126.7 . . ?
N3 C4 C5 131.3(3) . . ?
N3 C4 C9 106.4(2) . . ?
C5 C4 C9 122.2(3) . . ?
C6 C5 C4 116.3(3) . . ?
C6 C5 H5 121.9 . . ?
C4 C5 H5 121.9 . . ?
C5 C6 C7 121.7(3) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C8 C7 C6 121.8(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C9 C8 C7 117.1(3) . . ?
C9 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
C8 C9 N1 130.7(3) . . ?
C8 C9 C4 120.8(3) . . ?
N1 C9 C4 108.4(2) . . ?
C2 N10 N11 111.8(2) . . ?
C2 N10 C101 122.8(3) . . ?
N11 N10 C101 124.6(2) . . ?
C12 N11 N10 119.6(2) . . ?
C12 N11 Cu1 126.4(2) . . ?
N10 N11 Cu1 113.57(18) . . ?
N11 C12 C13 123.9(3) . . ?
N11 C12 H12 118.1 . . ?
C13 C12 H12 118.1 . . ?
C18 C13 C14 119.9(3) . . ?
C18 C13 C12 117.0(3) . . ?
C14 C13 C12 123.1(3) . . ?
C14 O14 Cu1 128.65(18) . . ?
O14 C14 C15 118.0(2) . . ?
O14 C14 C13 124.9(3) . . ?
C15 C14 C13 117.0(3) . . ?
O15 C15 C16 117.7(3) . . ?
O15 C15 C14 120.7(3) . . ?
C16 C15 C14 121.5(3) . . ?
C15 O15 C151 112.5(2) . . ?
O16 C16 C15 115.1(2) . . ?
O16 C16 C17 123.8(3) . . ?
C15 C16 C17 121.1(3) . . ?
C16 O16 C161 117.6(2) . . ?
C18 C17 C16 118.1(3) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 C13 122.3(3) . . ?
C17 C18 H18 118.8 . . ?
C13 C18 H18 118.8 . . ?
N10 C101 H10A 109.5 . . ?
N10 C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
N10 C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
O15 C151 H15A 109.5 . . ?
O15 C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
O15 C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16 C161 H16A 109.5 . . ?
O16 C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16 C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 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
C9 N1 C2 N10 -177.2(3) . . . . ?
Cu1 N1 C2 N10 4.9(3) . . . . ?
C9 N1 C2 N3 1.7(3) . . . . ?
Cu1 N1 C2 N3 -176.25(17) . . . . ?
N1 C2 N3 C4 -1.1(3) . . . . ?
N10 C2 N3 C4 177.7(3) . . . . ?
C2 N3 C4 C5 -178.3(3) . . . . ?
C2 N3 C4 C9 0.0(3) . . . . ?
N3 C4 C5 C6 176.1(3) . . . . ?
C9 C4 C5 C6 -1.9(4) . . . . ?
C4 C5 C6 C7 -1.0(4) . . . . ?
C5 C6 C7 C8 2.9(5) . . . . ?
C6 C7 C8 C9 -1.6(4) . . . . ?
C7 C8 C9 N1 -176.7(3) . . . . ?
C7 C8 C9 C4 -1.3(4) . . . . ?
C2 N1 C9 C8 174.2(3) . . . . ?
Cu1 N1 C9 C8 -8.9(5) . . . . ?
C2 N1 C9 C4 -1.7(3) . . . . ?
Cu1 N1 C9 C4 175.3(2) . . . . ?
N3 C4 C9 C8 -175.3(3) . . . . ?
C5 C4 C9 C8 3.1(4) . . . . ?
N3 C4 C9 N1 1.1(3) . . . . ?
C5 C4 C9 N1 179.5(3) . . . . ?
N1 C2 N10 N11 -2.5(4) . . . . ?
N3 C2 N10 N11 178.8(2) . . . . ?
N1 C2 N10 C101 167.7(3) . . . . ?
N3 C2 N10 C101 -11.1(5) . . . . ?
C2 N10 N11 C12 -174.7(3) . . . . ?
C101 N10 N11 C12 15.4(4) . . . . ?
C2 N10 N11 Cu1 -1.2(3) . . . . ?
C101 N10 N11 Cu1 -171.1(2) . . . . ?
N10 N11 C12 C13 -176.6(3) . . . . ?
Cu1 N11 C12 C13 10.8(4) . . . . ?
N11 C12 C13 C18 176.1(3) . . . . ?
N11 C12 C13 C14 -2.8(5) . . . . ?
N1 Cu1 O14 C14 60.1(5) . . . . ?
N11 Cu1 O14 C14 12.0(2) . . . . ?
Cl1 Cu1 O14 C14 -153.4(2) . . . . ?
Cu1 O14 C14 C15 171.60(19) . . . . ?
Cu1 O14 C14 C13 -8.6(4) . . . . ?
C18 C13 C14 O14 -177.6(3) . . . . ?
C12 C13 C14 O14 1.2(5) . . . . ?
C18 C13 C14 C15 2.2(4) . . . . ?
C12 C13 C14 C15 -179.0(3) . . . . ?
O14 C14 C15 O15 -1.7(4) . . . . ?
C13 C14 C15 O15 178.5(3) . . . . ?
O14 C14 C15 C16 176.8(3) . . . . ?
C13 C14 C15 C16 -3.1(4) . . . . ?
C16 C15 O15 C151 114.1(3) . . . . ?
C14 C15 O15 C151 -67.4(3) . . . . ?
O15 C15 C16 O16 1.1(4) . . . . ?
C14 C15 C16 O16 -177.4(3) . . . . ?
O15 C15 C16 C17 -179.5(3) . . . . ?
C14 C15 C16 C17 2.0(4) . . . . ?
C15 C16 O16 C161 178.6(3) . . . . ?
C17 C16 O16 C161 -0.8(4) . . . . ?
O16 C16 C17 C18 179.4(3) . . . . ?
C15 C16 C17 C18 0.0(4) . . . . ?
C16 C17 C18 C13 -0.8(5) . . . . ?
C14 C13 C18 C17 -0.3(5) . . . . ?
C12 C13 C18 C17 -179.2(3) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.064



####################################################################### 
# 
# 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_C6
_database_code_depnum_ccdc_archive 'CCDC 2370352'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-07-12 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cl2 Cu N8 O8, C H4 O'
_chemical_formula_sum            'C37 H44 Cl2 Cu N8 O9'
_chemical_formula_weight         879.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.26303(10)
_cell_length_b                   18.89895(16)
_cell_length_c                   17.09492(14)
_cell_angle_alpha                90
_cell_angle_beta                 97.1415(7)
_cell_angle_gamma                90
_cell_volume                     3931.15(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    22411
_cell_measurement_theta_min      3.4570
_cell_measurement_theta_max      75.5770

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             1828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    2.587
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.79320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5384
_diffrn_reflns_number            38953
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.501
_diffrn_reflns_theta_max         76.476
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8136
_reflns_number_gt                7345
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0624P)²+4.6621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8136
_refine_ls_number_parameters     524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0469
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.35072(3) 0.76683(2) 0.70522(2) 0.02445(10) Uani 1 1 d . . . . .
Cl1 Cl 0.23910(5) 0.85915(3) 0.66174(3) 0.03436(14) Uani 1 1 d . . . . .
N1A N 0.29796(15) 0.75437(10) 0.80679(11) 0.0259(4) Uani 1 1 d . . . . .
C2A C 0.32458(18) 0.69274(12) 0.84099(12) 0.0250(4) Uani 1 1 d . . . . .
N3A N 0.27674(15) 0.68152(10) 0.90649(11) 0.0271(4) Uani 1 1 d . . . . .
H3A H 0.283998 0.643838 0.936936 0.033 Uiso 1 1 calc R U . . .
C4A C 0.21349(18) 0.74114(13) 0.91672(13) 0.0269(4) Uani 1 1 d . . . . .
C5A C 0.14792(19) 0.75726(14) 0.97484(14) 0.0316(5) Uani 1 1 d . . . . .
H5A H 0.142018 0.726337 1.017923 0.038 Uiso 1 1 calc R U . . .
C6A C 0.0914(2) 0.82099(15) 0.96663(15) 0.0370(6) Uani 1 1 d . . . . .
H6A H 0.045330 0.834171 1.004951 0.044 Uiso 1 1 calc R U . . .
C7A C 0.1009(2) 0.86587(14) 0.90350(16) 0.0378(6) Uani 1 1 d . . . . .
H7A H 0.059729 0.908581 0.899077 0.045 Uiso 1 1 calc R U . . .
C8A C 0.1693(2) 0.84998(13) 0.84630(15) 0.0334(5) Uani 1 1 d . . . . .
H8A H 0.176466 0.881409 0.803871 0.040 Uiso 1 1 calc R U . . .
C9A C 0.22621(18) 0.78635(13) 0.85404(13) 0.0264(4) Uani 1 1 d . . . . .
N10A N 0.39383(17) 0.64649(10) 0.81128(11) 0.0292(4) Uani 1 1 d . . . . .
C10A C 0.4107(2) 0.57465(13) 0.83908(15) 0.0356(5) Uani 1 1 d . . . . .
H10A H 0.398792 0.542002 0.794300 0.053 Uiso 1 1 calc R U . . .
H10B H 0.358729 0.563814 0.876570 0.053 Uiso 1 1 calc R U . . .
H10C H 0.486034 0.569415 0.865240 0.053 Uiso 1 1 calc R U . . .
N11A N 0.45553(15) 0.67788(10) 0.75744(11) 0.0261(4) Uani 1 1 d . . . . .
C12A C 0.53110(19) 0.64020(13) 0.73202(14) 0.0295(5) Uani 1 1 d . . . . .
H12A H 0.532739 0.590766 0.742195 0.035 Uiso 1 1 calc R U . . .
C13A C 0.61448(18) 0.67073(13) 0.68805(13) 0.0281(5) Uani 1 1 d . . . . .
C14A C 0.66669(19) 0.62789(12) 0.63691(14) 0.0291(5) Uani 1 1 d . . . . .
O14A O 0.62537(15) 0.56034(9) 0.62194(11) 0.0372(4) Uani 1 1 d . . . . .
C141 C 0.6881(3) 0.50649(16) 0.6654(2) 0.0524(8) Uani 1 1 d . . . . .
H14A H 0.763601 0.507217 0.652162 0.079 Uiso 1 1 calc R U . . .
H14B H 0.655031 0.460186 0.651869 0.079 Uiso 1 1 calc R U . . .
H14C H 0.688782 0.515080 0.721988 0.079 Uiso 1 1 calc R U . . .
C15A C 0.75261(19) 0.65299(13) 0.59834(14) 0.0308(5) Uani 1 1 d . . . . .
C151 C 0.8061(2) 0.60771(15) 0.54097(18) 0.0435(6) Uani 1 1 d . . . . .
H15A H 0.815798 0.635617 0.494008 0.065 Uiso 1 1 calc R U . . .
H15B H 0.759325 0.566729 0.525685 0.065 Uiso 1 1 calc R U . . .
H15C H 0.877969 0.591435 0.566033 0.065 Uiso 1 1 calc R U . . .
C16A C 0.78703(18) 0.72256(13) 0.61358(14) 0.0297(5) Uani 1 1 d . . . . .
O16A O 0.87245(14) 0.74421(10) 0.57451(11) 0.0365(4) Uani 1 1 d . . . . .
C161 C 0.9110(2) 0.81465(15) 0.5874(2) 0.0453(7) Uani 1 1 d . . . . .
H16A H 0.969414 0.824009 0.554437 0.068 Uiso 1 1 calc R U . . .
H16B H 0.940055 0.820716 0.642998 0.068 Uiso 1 1 calc R U . . .
H16C H 0.850286 0.847824 0.573487 0.068 Uiso 1 1 calc R U . . .
C17A C 0.7370(2) 0.76628(13) 0.66401(15) 0.0337(5) Uani 1 1 d . . . . .
H17A H 0.761604 0.813545 0.673295 0.040 Uiso 1 1 calc R U . . .
C18A C 0.65063(19) 0.73998(13) 0.70056(15) 0.0322(5) Uani 1 1 d . . . . .
H18A H 0.615664 0.769750 0.734664 0.039 Uiso 1 1 calc R U . . .
N1B N 0.41102(15) 0.76013(9) 0.60628(11) 0.0239(4) Uani 1 1 d . . . . .
C2B C 0.40557(17) 0.70041(11) 0.56501(12) 0.0227(4) Uani 1 1 d . . . . .
N3B N 0.46666(15) 0.70302(10) 0.50430(11) 0.0244(4) Uani 1 1 d . . . . .
H3B H 0.473567 0.669158 0.469927 0.029 Uiso 1 1 calc R U . . .
C4B C 0.51640(18) 0.76915(12) 0.50645(13) 0.0249(4) Uani 1 1 d . . . . .
C5B C 0.58906(18) 0.79873(13) 0.45982(14) 0.0294(5) Uani 1 1 d . . . . .
H5B H 0.613761 0.773473 0.417307 0.035 Uiso 1 1 calc R U . . .
C6B C 0.6238(2) 0.86716(14) 0.47848(16) 0.0352(5) Uani 1 1 d . . . . .
H6B H 0.673758 0.889504 0.448060 0.042 Uiso 1 1 calc R U . . .
C7B C 0.5869(2) 0.90407(14) 0.54123(17) 0.0370(6) Uani 1 1 d . . . . .
H7B H 0.612023 0.951029 0.552078 0.044 Uiso 1 1 calc R U . . .
C8B C 0.5145(2) 0.87375(13) 0.58806(15) 0.0322(5) Uani 1 1 d . . . . .
H8B H 0.489895 0.898878 0.630713 0.039 Uiso 1 1 calc R U . . .
C9B C 0.47979(17) 0.80539(12) 0.56978(13) 0.0246(4) Uani 1 1 d . . . . .
N10B N 0.34499(16) 0.64315(10) 0.58094(11) 0.0264(4) Uani 1 1 d . . . . .
C10B C 0.3509(2) 0.57568(12) 0.54084(16) 0.0345(5) Uani 1 1 d . . . . .
H10D H 0.355159 0.537233 0.579563 0.052 Uiso 1 1 calc R U . . .
H10E H 0.416413 0.574783 0.513336 0.052 Uiso 1 1 calc R U . . .
H10F H 0.285151 0.569541 0.502575 0.052 Uiso 1 1 calc R U . . .
N11B N 0.26990(15) 0.65667(10) 0.63368(11) 0.0259(4) Uani 1 1 d . . . . .
C12B C 0.2008(2) 0.60768(13) 0.64476(15) 0.0340(5) Uani 1 1 d . . . . .
H12B H 0.204540 0.563289 0.619155 0.041 Uiso 1 1 calc R U . . .
C13B C 0.1163(2) 0.61992(14) 0.69662(15) 0.0332(5) Uani 1 1 d . . . . .
C14B C 0.0607(2) 0.56234(15) 0.72559(17) 0.0407(6) Uani 1 1 d . . . . .
O14B O 0.07803(19) 0.49558(11) 0.69585(13) 0.0504(5) Uani 1 1 d . . . . .
C142 C 0.1513(3) 0.4552(2) 0.7457(2) 0.0685(10) Uani 1 1 d . . . . .
H14D H 0.119708 0.445299 0.794451 0.103 Uiso 1 1 calc R U . . .
H14E H 0.220366 0.481224 0.758118 0.103 Uiso 1 1 calc R U . . .
H14F H 0.165479 0.410522 0.719640 0.103 Uiso 1 1 calc R U . . .
C15B C -0.0144(2) 0.57088(16) 0.77994(16) 0.0409(6) Uani 1 1 d . . . . .
C152 C -0.0720(3) 0.50847(18) 0.8116(2) 0.0528(8) Uani 1 1 d . . . . .
H15D H -0.033261 0.494565 0.862880 0.079 Uiso 1 1 calc R U . . .
H15E H -0.072488 0.468743 0.774710 0.079 Uiso 1 1 calc R U . . .
H15F H -0.147827 0.521600 0.817725 0.079 Uiso 1 1 calc R U . . .
C16B C -0.03799(19) 0.63932(15) 0.80170(14) 0.0339(5) Uani 1 1 d . . . . .
O16B O -0.11122(15) 0.64441(11) 0.85581(11) 0.0427(5) Uani 1 1 d . . . . .
C162 C -0.1442(2) 0.71387(17) 0.87630(17) 0.0443(6) Uani 1 1 d . . . . .
H16D H -0.183475 0.736875 0.829688 0.066 Uiso 1 1 calc R U . . .
H16E H -0.079075 0.741788 0.895674 0.066 Uiso 1 1 calc R U . . .
H16F H -0.192723 0.710553 0.917596 0.066 Uiso 1 1 calc R U . . .
C17B C 0.00852(19) 0.69757(14) 0.76880(14) 0.0325(5) Uani 1 1 d . . . . .
H17B H -0.011997 0.744147 0.781920 0.039 Uiso 1 1 calc R U . . .
C18B C 0.08489(18) 0.68712(13) 0.71683(14) 0.0299(5) Uani 1 1 d . . . . .
H18B H 0.116534 0.727037 0.694478 0.036 Uiso 1 1 calc R U . . .
Cl1C Cl 0.57296(5) 0.89370(3) 0.83857(3) 0.03523(15) Uani 1 1 d . . . . .
O1C O 0.4915(2) 0.85191(17) 0.7959(2) 0.0927(12) Uani 1 1 d . . . . .
O2C O 0.6746(2) 0.85536(13) 0.84695(14) 0.0601(6) Uani 1 1 d . . . . .
O3C O 0.5856(2) 0.95853(12) 0.80025(15) 0.0685(7) Uani 1 1 d . . . . .
O4C O 0.5438(2) 0.90960(11) 0.91578(13) 0.0637(7) Uani 1 1 d . . . . .
C1D C 0.1614(3) 0.9630(2) 0.4833(2) 0.0581(9) Uani 1 1 d . . . . .
H1DA H 0.150244 0.973993 0.426866 0.087 Uiso 1 1 calc R U . . .
H1DB H 0.152582 1.006221 0.513628 0.087 Uiso 1 1 calc R U . . .
H1DC H 0.107072 0.927839 0.495236 0.087 Uiso 1 1 calc R U . . .
O1D O 0.26873(16) 0.93553(10) 0.50394(10) 0.0397(4) Uani 1 1 d . . . . .
H1D H 0.274396 0.919212 0.549978 0.060 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 N1B 1.9325(18) . ?
Cu1 N1A 1.9411(19) . ?
Cu1 N11A 2.2338(19) . ?
Cu1 Cl1 2.2841(6) . ?
N1A C2A 1.326(3) . ?
N1A C9A 1.403(3) . ?
C2A N3A 1.344(3) . ?
C2A N10A 1.360(3) . ?
N3A C4A 1.391(3) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.388(3) . ?
C4A C9A 1.394(3) . ?
C5A C6A 1.388(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.389(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.398(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.389(3) . ?
C8A H8A 0.9500 . ?
N10A N11A 1.394(3) . ?
N10A C10A 1.445(3) . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
N11A C12A 1.286(3) . ?
C12A C13A 1.461(3) . ?
C12A H12A 0.9500 . ?
C13A C18A 1.390(3) . ?
C13A C14A 1.403(3) . ?
C14A O14A 1.385(3) . ?
C14A C15A 1.394(3) . ?
O14A C141 1.427(3) . ?
C141 H14A 0.9800 . ?
C141 H14B 0.9800 . ?
C141 H14C 0.9800 . ?
C15A C16A 1.395(4) . ?
C15A C151 1.511(3) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C16A O16A 1.373(3) . ?
C16A C17A 1.391(3) . ?
O16A C161 1.421(3) . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C17A C18A 1.387(4) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
N1B C2B 1.328(3) . ?
N1B C9B 1.401(3) . ?
C2B N3B 1.354(3) . ?
C2B N10B 1.359(3) . ?
N3B C4B 1.389(3) . ?
N3B H3B 0.8800 . ?
C4B C5B 1.385(3) . ?
C4B C9B 1.401(3) . ?
C5B C6B 1.386(4) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.401(4) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.391(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.384(3) . ?
C8B H8B 0.9500 . ?
N10B N11B 1.390(2) . ?
N10B C10B 1.454(3) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
N11B C12B 1.285(3) . ?
C12B C13B 1.463(3) . ?
C12B H12B 0.9500 . ?
C13B C18B 1.383(4) . ?
C13B C14B 1.406(3) . ?
C14B O14B 1.386(3) . ?
C14B C15B 1.396(4) . ?
O14B C142 1.387(4) . ?
C142 H14D 0.9800 . ?
C142 H14E 0.9800 . ?
C142 H14F 0.9800 . ?
C15B C16B 1.386(4) . ?
C15B C152 1.510(4) . ?
C152 H15D 0.9800 . ?
C152 H15E 0.9800 . ?
C152 H15F 0.9800 . ?
C16B O16B 1.370(3) . ?
C16B C17B 1.390(3) . ?
O16B C162 1.430(4) . ?
C162 H16D 0.9800 . ?
C162 H16E 0.9800 . ?
C162 H16F 0.9800 . ?
C17B C18B 1.383(3) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
Cl1C O1C 1.404(2) . ?
Cl1C O3C 1.407(2) . ?
Cl1C O2C 1.433(2) . ?
Cl1C O4C 1.441(2) . ?
C1D O1D 1.419(4) . ?
C1D H1DA 0.9800 . ?
C1D H1DB 0.9800 . ?
C1D H1DC 0.9800 . ?
O1D H1D 0.8400 . ?

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
N1B Cu1 N1A 168.89(8) . . ?
N1B Cu1 N11A 92.10(7) . . ?
N1A Cu1 N11A 77.91(7) . . ?
N1B Cu1 Cl1 92.54(6) . . ?
N1A Cu1 Cl1 97.52(6) . . ?
N11A Cu1 Cl1 175.33(5) . . ?
C2A N1A C9A 105.20(18) . . ?
C2A N1A Cu1 114.20(15) . . ?
C9A N1A Cu1 139.94(16) . . ?
N1A C2A N3A 113.39(19) . . ?
N1A C2A N10A 122.1(2) . . ?
N3A C2A N10A 124.5(2) . . ?
C2A N3A C4A 106.54(19) . . ?
C2A N3A H3A 126.7 . . ?
C4A N3A H3A 126.7 . . ?
C5A C4A N3A 130.5(2) . . ?
C5A C4A C9A 123.1(2) . . ?
N3A C4A C9A 106.40(19) . . ?
C4A C5A C6A 116.4(2) . . ?
C4A C5A H5A 121.8 . . ?
C6A C5A H5A 121.8 . . ?
C5A C6A C7A 121.3(2) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C6A C7A C8A 121.9(2) . . ?
C6A C7A H7A 119.1 . . ?
C8A C7A H7A 119.1 . . ?
C9A C8A C7A 117.2(2) . . ?
C9A C8A H8A 121.4 . . ?
C7A C8A H8A 121.4 . . ?
C8A C9A C4A 120.1(2) . . ?
C8A C9A N1A 131.5(2) . . ?
C4A C9A N1A 108.5(2) . . ?
C2A N10A N11A 112.84(18) . . ?
C2A N10A C10A 123.47(19) . . ?
N11A N10A C10A 123.34(19) . . ?
N10A C10A H10A 109.5 . . ?
N10A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
N10A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C12A N11A N10A 117.40(19) . . ?
C12A N11A Cu1 133.19(16) . . ?
N10A N11A Cu1 104.56(13) . . ?
N11A C12A C13A 122.3(2) . . ?
N11A C12A H12A 118.8 . . ?
C13A C12A H12A 118.8 . . ?
C18A C13A C14A 118.5(2) . . ?
C18A C13A C12A 121.5(2) . . ?
C14A C13A C12A 119.7(2) . . ?
O14A C14A C15A 120.5(2) . . ?
O14A C14A C13A 117.5(2) . . ?
C15A C14A C13A 121.9(2) . . ?
C14A O14A C141 113.6(2) . . ?
O14A C141 H14A 109.5 . . ?
O14A C141 H14B 109.5 . . ?
H14A C141 H14B 109.5 . . ?
O14A C141 H14C 109.5 . . ?
H14A C141 H14C 109.5 . . ?
H14B C141 H14C 109.5 . . ?
C14A C15A C16A 117.5(2) . . ?
C14A C15A C151 121.9(2) . . ?
C16A C15A C151 120.6(2) . . ?
C15A C151 H15A 109.5 . . ?
C15A C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
C15A C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16A C16A C17A 123.1(2) . . ?
O16A C16A C15A 114.9(2) . . ?
C17A C16A C15A 121.9(2) . . ?
C16A O16A C161 117.6(2) . . ?
O16A C161 H16A 109.5 . . ?
O16A C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16A C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C18A C17A C16A 119.1(2) . . ?
C18A C17A H17A 120.4 . . ?
C16A C17A H17A 120.4 . . ?
C17A C18A C13A 121.0(2) . . ?
C17A C18A H18A 119.5 . . ?
C13A C18A H18A 119.5 . . ?
C2B N1B C9B 105.99(18) . . ?
C2B N1B Cu1 121.40(15) . . ?
C9B N1B Cu1 131.82(15) . . ?
N1B C2B N3B 112.33(19) . . ?
N1B C2B N10B 124.25(19) . . ?
N3B C2B N10B 123.41(19) . . ?
C2B N3B C4B 107.18(18) . . ?
C2B N3B H3B 126.4 . . ?
C4B N3B H3B 126.4 . . ?
C5B C4B N3B 131.3(2) . . ?
C5B C4B C9B 122.6(2) . . ?
N3B C4B C9B 106.17(18) . . ?
C4B C5B C6B 116.5(2) . . ?
C4B C5B H5B 121.8 . . ?
C6B C5B H5B 121.8 . . ?
C5B C6B C7B 121.4(2) . . ?
C5B C6B H6B 119.3 . . ?
C7B C6B H6B 119.3 . . ?
C8B C7B C6B 121.7(2) . . ?
C8B C7B H7B 119.1 . . ?
C6B C7B H7B 119.1 . . ?
C9B C8B C7B 117.1(2) . . ?
C9B C8B H8B 121.5 . . ?
C7B C8B H8B 121.5 . . ?
C8B C9B N1B 130.9(2) . . ?
C8B C9B C4B 120.8(2) . . ?
N1B C9B C4B 108.31(19) . . ?
C2B N10B N11B 113.96(18) . . ?
C2B N10B C10B 122.91(18) . . ?
N11B N10B C10B 122.89(18) . . ?
N10B C10B H10D 109.5 . . ?
N10B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
N10B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C12B N11B N10B 117.74(19) . . ?
N11B C12B C13B 120.3(2) . . ?
N11B C12B H12B 119.8 . . ?
C13B C12B H12B 119.8 . . ?
C18B C13B C14B 117.4(2) . . ?
C18B C13B C12B 122.5(2) . . ?
C14B C13B C12B 120.1(2) . . ?
O14B C14B C15B 119.5(2) . . ?
O14B C14B C13B 118.2(2) . . ?
C15B C14B C13B 122.2(3) . . ?
C14B O14B C142 113.1(3) . . ?
O14B C142 H14D 109.5 . . ?
O14B C142 H14E 109.5 . . ?
H14D C142 H14E 109.5 . . ?
O14B C142 H14F 109.5 . . ?
H14D C142 H14F 109.5 . . ?
H14E C142 H14F 109.5 . . ?
C16B C15B C14B 117.6(2) . . ?
C16B C15B C152 120.7(2) . . ?
C14B C15B C152 121.7(3) . . ?
C15B C152 H15D 109.5 . . ?
C15B C152 H15E 109.5 . . ?
H15D C152 H15E 109.5 . . ?
C15B C152 H15F 109.5 . . ?
H15D C152 H15F 109.5 . . ?
H15E C152 H15F 109.5 . . ?
O16B C16B C15B 115.0(2) . . ?
O16B C16B C17B 123.6(2) . . ?
C15B C16B C17B 121.4(2) . . ?
C16B O16B C162 117.3(2) . . ?
O16B C162 H16D 109.5 . . ?
O16B C162 H16E 109.5 . . ?
H16D C162 H16E 109.5 . . ?
O16B C162 H16F 109.5 . . ?
H16D C162 H16F 109.5 . . ?
H16E C162 H16F 109.5 . . ?
C18B C17B C16B 119.4(2) . . ?
C18B C17B H17B 120.3 . . ?
C16B C17B H17B 120.3 . . ?
C17B C18B C13B 121.6(2) . . ?
C17B C18B H18B 119.2 . . ?
C13B C18B H18B 119.2 . . ?
O1C Cl1C O3C 111.1(2) . . ?
O1C Cl1C O2C 108.71(16) . . ?
O3C Cl1C O2C 110.02(16) . . ?
O1C Cl1C O4C 110.60(18) . . ?
O3C Cl1C O4C 107.39(14) . . ?
O2C Cl1C O4C 108.98(16) . . ?
O1D C1D H1DA 109.5 . . ?
O1D C1D H1DB 109.5 . . ?
H1DA C1D H1DB 109.5 . . ?
O1D C1D H1DC 109.5 . . ?
H1DA C1D H1DC 109.5 . . ?
H1DB C1D H1DC 109.5 . . ?
C1D O1D H1D 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
C9A N1A C2A N3A -0.1(3) . . . . ?
Cu1 N1A C2A N3A -172.59(15) . . . . ?
C9A N1A C2A N10A 180.0(2) . . . . ?
Cu1 N1A C2A N10A 7.4(3) . . . . ?
N1A C2A N3A C4A -0.4(3) . . . . ?
N10A C2A N3A C4A 179.6(2) . . . . ?
C2A N3A C4A C5A -179.7(2) . . . . ?
C2A N3A C4A C9A 0.7(2) . . . . ?
N3A C4A C5A C6A -177.7(2) . . . . ?
C9A C4A C5A C6A 1.9(4) . . . . ?
C4A C5A C6A C7A -0.2(4) . . . . ?
C5A C6A C7A C8A -1.4(4) . . . . ?
C6A C7A C8A C9A 1.3(4) . . . . ?
C7A C8A C9A C4A 0.3(4) . . . . ?
C7A C8A C9A N1A 178.3(2) . . . . ?
C5A C4A C9A C8A -2.0(4) . . . . ?
N3A C4A C9A C8A 177.7(2) . . . . ?
C5A C4A C9A N1A 179.6(2) . . . . ?
N3A C4A C9A N1A -0.7(2) . . . . ?
C2A N1A C9A C8A -177.6(3) . . . . ?
Cu1 N1A C9A C8A -8.2(4) . . . . ?
C2A N1A C9A C4A 0.5(2) . . . . ?
Cu1 N1A C9A C4A 169.87(18) . . . . ?
N1A C2A N10A N11A 17.0(3) . . . . ?
N3A C2A N10A N11A -163.0(2) . . . . ?
N1A C2A N10A C10A -169.6(2) . . . . ?
N3A C2A N10A C10A 10.5(4) . . . . ?
C2A N10A N11A C12A 173.3(2) . . . . ?
C10A N10A N11A C12A -0.1(3) . . . . ?
C2A N10A N11A Cu1 -28.1(2) . . . . ?
C10A N10A N11A Cu1 158.48(19) . . . . ?
N10A N11A C12A C13A -167.8(2) . . . . ?
Cu1 N11A C12A C13A 41.1(3) . . . . ?
N11A C12A C13A C18A 30.0(4) . . . . ?
N11A C12A C13A C14A -155.6(2) . . . . ?
C18A C13A C14A O14A -176.5(2) . . . . ?
C12A C13A C14A O14A 9.0(3) . . . . ?
C18A C13A C14A C15A -0.4(4) . . . . ?
C12A C13A C14A C15A -174.9(2) . . . . ?
C15A C14A O14A C141 82.4(3) . . . . ?
C13A C14A O14A C141 -101.4(3) . . . . ?
O14A C14A C15A C16A 177.3(2) . . . . ?
C13A C14A C15A C16A 1.3(3) . . . . ?
O14A C14A C15A C151 -1.7(4) . . . . ?
C13A C14A C15A C151 -177.7(2) . . . . ?
C14A C15A C16A O16A 179.5(2) . . . . ?
C151 C15A C16A O16A -1.5(3) . . . . ?
C14A C15A C16A C17A -1.2(4) . . . . ?
C151 C15A C16A C17A 177.8(2) . . . . ?
C17A C16A O16A C161 0.5(4) . . . . ?
C15A C16A O16A C161 179.8(2) . . . . ?
O16A C16A C17A C18A 179.6(2) . . . . ?
C15A C16A C17A C18A 0.3(4) . . . . ?
C16A C17A C18A C13A 0.6(4) . . . . ?
C14A C13A C18A C17A -0.5(4) . . . . ?
C12A C13A C18A C17A 173.9(2) . . . . ?
C9B N1B C2B N3B 0.5(2) . . . . ?
Cu1 N1B C2B N3B -170.49(14) . . . . ?
C9B N1B C2B N10B -178.9(2) . . . . ?
Cu1 N1B C2B N10B 10.1(3) . . . . ?
N1B C2B N3B C4B 0.5(2) . . . . ?
N10B C2B N3B C4B 179.9(2) . . . . ?
C2B N3B C4B C5B 178.0(2) . . . . ?
C2B N3B C4B C9B -1.3(2) . . . . ?
N3B C4B C5B C6B -179.7(2) . . . . ?
C9B C4B C5B C6B -0.5(3) . . . . ?
C4B C5B C6B C7B -0.1(4) . . . . ?
C5B C6B C7B C8B 0.5(4) . . . . ?
C6B C7B C8B C9B -0.3(4) . . . . ?
C7B C8B C9B N1B 177.8(2) . . . . ?
C7B C8B C9B C4B -0.3(4) . . . . ?
C2B N1B C9B C8B -179.6(2) . . . . ?
Cu1 N1B C9B C8B -9.9(4) . . . . ?
C2B N1B C9B C4B -1.3(2) . . . . ?
Cu1 N1B C9B C4B 168.37(16) . . . . ?
C5B C4B C9B C8B 0.7(4) . . . . ?
N3B C4B C9B C8B -179.9(2) . . . . ?
C5B C4B C9B N1B -177.8(2) . . . . ?
N3B C4B C9B N1B 1.6(2) . . . . ?
N1B C2B N10B N11B 13.1(3) . . . . ?
N3B C2B N10B N11B -166.22(19) . . . . ?
N1B C2B N10B C10B -172.4(2) . . . . ?
N3B C2B N10B C10B 8.3(3) . . . . ?
C2B N10B N11B C12B 172.1(2) . . . . ?
C10B N10B N11B C12B -2.5(3) . . . . ?
N10B N11B C12B C13B -177.0(2) . . . . ?
N11B C12B C13B C18B 19.6(4) . . . . ?
N11B C12B C13B C14B -162.9(3) . . . . ?
C18B C13B C14B O14B 169.6(2) . . . . ?
C12B C13B C14B O14B -8.1(4) . . . . ?
C18B C13B C14B C15B -7.3(4) . . . . ?
C12B C13B C14B C15B 175.0(3) . . . . ?
C15B C14B O14B C142 -82.2(4) . . . . ?
C13B C14B O14B C142 100.8(3) . . . . ?
O14B C14B C15B C16B -173.2(3) . . . . ?
C13B C14B C15B C16B 3.7(4) . . . . ?
O14B C14B C15B C152 4.1(5) . . . . ?
C13B C14B C15B C152 -178.9(3) . . . . ?
C14B C15B C16B O16B -179.3(2) . . . . ?
C152 C15B C16B O16B 3.3(4) . . . . ?
C14B C15B C16B C17B 2.0(4) . . . . ?
C152 C15B C16B C17B -175.4(3) . . . . ?
C15B C16B O16B C162 -175.9(2) . . . . ?
C17B C16B O16B C162 2.8(4) . . . . ?
O16B C16B C17B C18B 177.6(2) . . . . ?
C15B C16B C17B C18B -3.9(4) . . . . ?
C16B C17B C18B C13B 0.0(4) . . . . ?
C14B C13B C18B C17B 5.4(4) . . . . ?
C12B C13B C18B C17B -177.0(2) . . . . ?

_refine_diff_density_max         1.160
_refine_diff_density_min         -0.452
_refine_diff_density_rms         0.067



####################################################################### 
# 
# 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_C3
_database_code_depnum_ccdc_archive 'CCDC 2336939'
loop_
_audit_author_name
_audit_author_address
'Maciej Kubicki'
;Adam Mickiewicz University
Poland
;
_audit_update_record             
;
2024-03-01 deposited with the CCDC.	2026-01-30 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
C35 H38 Cl Cu2 N8 O7, Cl O4, 2(C H4 O), O
;
_chemical_formula_sum            'C37 H46 Cl2 Cu2 N8 O14'
_chemical_formula_weight         1024.80

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   16.90445(13)
_cell_length_b                   12.18931(8)
_cell_length_c                   22.04368(13)
_cell_angle_alpha                90
_cell_angle_beta                 101.9124(7)
_cell_angle_gamma                90
_cell_volume                     4444.36(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    34154
_cell_measurement_theta_min      2.6500
_cell_measurement_theta_max      76.0170

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.918
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.58696
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.116a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.2692
_diffrn_reflns_number            51157
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.671
_diffrn_reflns_theta_max         76.325
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9267
_reflns_number_gt                8481
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.116a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0776P)²+4.9944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     .
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9267
_refine_ls_number_parameters     601
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0440
_refine_ls_wR_factor_ref         0.1308
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1A Cu 0.67198(2) 0.59157(3) 0.49516(2) 0.02588(10) Uani 1 1 d . . . . .
N1A N 0.63111(12) 0.68342(17) 0.42247(9) 0.0287(4) Uani 1 1 d . . . . .
C2A C 0.56274(15) 0.7332(2) 0.42595(11) 0.0314(5) Uani 1 1 d . . . . .
N3A N 0.53623(14) 0.80366(19) 0.37891(10) 0.0377(5) Uani 1 1 d . . . . .
H3A H 0.492952 0.845545 0.373719 0.045 Uiso 1 1 calc R U . . .
C4A C 0.59157(16) 0.7963(2) 0.34039(12) 0.0353(5) Uani 1 1 d . . . . .
C5A C 0.59299(19) 0.8489(3) 0.28477(13) 0.0439(6) Uani 1 1 d . . . . .
H5A H 0.552375 0.899985 0.266907 0.053 Uiso 1 1 calc R U . . .
C6A C 0.65672(19) 0.8231(3) 0.25667(13) 0.0454(7) Uani 1 1 d . . . . .
H6A H 0.660313 0.857696 0.218723 0.054 Uiso 1 1 calc R U . . .
C7A C 0.71536(18) 0.7477(3) 0.28275(12) 0.0413(6) Uani 1 1 d . . . . .
H7A H 0.757872 0.731435 0.261931 0.050 Uiso 1 1 calc R U . . .
C8A C 0.71376(15) 0.6951(2) 0.33862(11) 0.0345(5) Uani 1 1 d . . . . .
H8A H 0.754136 0.643470 0.356139 0.041 Uiso 1 1 calc R U . . .
C9A C 0.65060(15) 0.7214(2) 0.36767(11) 0.0305(5) Uani 1 1 d . . . . .
N10A N 0.52467(13) 0.71220(19) 0.47325(10) 0.0366(5) Uani 1 1 d . . . . .
C101 C 0.44646(17) 0.7541(2) 0.47822(14) 0.0419(6) Uani 1 1 d . . . . .
H10A H 0.407840 0.693338 0.474854 0.063 Uiso 1 1 calc R U . . .
H10B H 0.427802 0.806908 0.444812 0.063 Uiso 1 1 calc R U . . .
H10C H 0.450617 0.790533 0.518391 0.063 Uiso 1 1 calc R U . . .
N11A N 0.56574(12) 0.63401(17) 0.51375(9) 0.0290(4) Uani 1 1 d . . . . .
C12A C 0.53322(14) 0.5975(2) 0.55804(11) 0.0291(5) Uani 1 1 d . . . . .
H12A H 0.481238 0.624091 0.560733 0.035 Uiso 1 1 calc R U . . .
C13A C 0.57122(14) 0.5191(2) 0.60325(10) 0.0285(5) Uani 1 1 d . . . . .
O14A O 0.69820(10) 0.50317(14) 0.56874(7) 0.0290(3) Uani 1 1 d . . . . .
C14A C 0.65104(14) 0.47780(19) 0.60717(10) 0.0265(4) Uani 1 1 d . . . . .
O15A O 0.75778(11) 0.36303(16) 0.66238(8) 0.0362(4) Uani 1 1 d . . . . .
C15A C 0.68064(16) 0.4054(2) 0.65651(10) 0.0304(5) Uani 1 1 d . . . . .
C151 C 0.81790(19) 0.4308(3) 0.70048(15) 0.0535(8) Uani 1 1 d . . . . .
H15A H 0.821537 0.501062 0.679629 0.080 Uiso 1 1 calc R U . . .
H15B H 0.870422 0.393667 0.707328 0.080 Uiso 1 1 calc R U . . .
H15C H 0.802721 0.443815 0.740440 0.080 Uiso 1 1 calc R U . . .
C16A C 0.63435(17) 0.3738(2) 0.69915(11) 0.0344(5) Uani 1 1 d . . . . .
O16A O 0.67205(13) 0.30444(18) 0.74426(9) 0.0455(5) Uani 1 1 d . . . . .
C161 C 0.6285(2) 0.2707(3) 0.79010(14) 0.0575(9) Uani 1 1 d . . . . .
H16A H 0.578554 0.233501 0.769906 0.086 Uiso 1 1 calc R U . . .
H16B H 0.615099 0.335110 0.812593 0.086 Uiso 1 1 calc R U . . .
H16C H 0.661877 0.220192 0.819254 0.086 Uiso 1 1 calc R U . . .
C17A C 0.55570(17) 0.4125(2) 0.69350(11) 0.0354(5) Uani 1 1 d . . . . .
H17A H 0.523401 0.389589 0.721679 0.042 Uiso 1 1 calc R U . . .
C18A C 0.52566(15) 0.4845(2) 0.64651(11) 0.0323(5) Uani 1 1 d . . . . .
H18A H 0.472292 0.511823 0.643022 0.039 Uiso 1 1 calc R U . . .
Cu1B Cu 0.80730(2) 0.43561(3) 0.44901(2) 0.02645(10) Uani 1 1 d . . . . .
N1B N 0.84327(13) 0.30115(17) 0.41491(9) 0.0312(4) Uani 1 1 d . . . . .
C2B C 0.90518(15) 0.3179(2) 0.38776(11) 0.0309(5) Uani 1 1 d . . . . .
N3B N 0.92777(14) 0.22660(18) 0.36130(10) 0.0358(5) Uani 1 1 d . . . . .
H3B H 0.966896 0.221180 0.340608 0.043 Uiso 1 1 calc R U . . .
C4B C 0.87717(17) 0.1424(2) 0.37306(11) 0.0372(5) Uani 1 1 d . . . . .
C5B C 0.8759(2) 0.0312(2) 0.35899(13) 0.0478(7) Uani 1 1 d . . . . .
H5B H 0.913267 -0.000188 0.337130 0.057 Uiso 1 1 calc R U . . .
C6B C 0.8178(2) -0.0314(3) 0.37836(15) 0.0555(8) Uani 1 1 d . . . . .
H6B H 0.814765 -0.107688 0.369432 0.067 Uiso 1 1 calc R U . . .
C7B C 0.7632(2) 0.0149(3) 0.41077(16) 0.0544(8) Uani 1 1 d . . . . .
H7B H 0.724002 -0.030818 0.423324 0.065 Uiso 1 1 calc R U . . .
C8B C 0.76487(19) 0.1267(2) 0.42523(14) 0.0447(6) Uani 1 1 d . . . . .
H8B H 0.727572 0.157964 0.447150 0.054 Uiso 1 1 calc R U . . .
C9B C 0.82355(16) 0.1897(2) 0.40605(12) 0.0355(5) Uani 1 1 d . . . . .
N10B N 0.93995(13) 0.41816(17) 0.38828(10) 0.0329(4) Uani 1 1 d . . . . .
C102 C 1.01455(16) 0.4406(2) 0.36735(13) 0.0371(5) Uani 1 1 d . . . . .
H10D H 1.006190 0.502470 0.338368 0.056 Uiso 1 1 calc R U . . .
H10E H 1.030241 0.375541 0.346484 0.056 Uiso 1 1 calc R U . . .
H10F H 1.057450 0.458743 0.403107 0.056 Uiso 1 1 calc R U . . .
N11B N 0.90586(12) 0.49362(16) 0.42282(9) 0.0276(4) Uani 1 1 d . . . . .
C12B C 0.93817(15) 0.5888(2) 0.43384(11) 0.0298(5) Uani 1 1 d . . . . .
H12B H 0.984699 0.605068 0.417589 0.036 Uiso 1 1 calc R U . . .
C13B C 0.90811(14) 0.67251(19) 0.46935(10) 0.0287(5) Uani 1 1 d . . . . .
C14B C 0.83565(13) 0.66482(18) 0.49204(10) 0.0254(4) Uani 1 1 d . . . . .
O14B O 0.78559(10) 0.57899(13) 0.48040(8) 0.0277(3) Uani 1 1 d . . . . .
O15B O 0.74427(10) 0.74488(14) 0.54874(7) 0.0307(3) Uani 1 1 d . . . . .
C15B C 0.81582(14) 0.75182(19) 0.52787(10) 0.0283(4) Uani 1 1 d . . . . .
C152 C 0.75458(19) 0.7393(2) 0.61557(12) 0.0420(6) Uani 1 1 d . . . . .
H15D H 0.701703 0.730231 0.626614 0.063 Uiso 1 1 calc R U . . .
H15E H 0.779776 0.807257 0.634017 0.063 Uiso 1 1 calc R U . . .
H15F H 0.789237 0.676820 0.631290 0.063 Uiso 1 1 calc R U . . .
O16B O 0.83639(12) 0.92529(15) 0.57254(9) 0.0391(4) Uani 1 1 d . . . . .
C16B C 0.86428(16) 0.8456(2) 0.53952(11) 0.0325(5) Uani 1 1 d . . . . .
C162 C 0.8894(2) 1.0143(3) 0.5943(2) 0.0648(10) Uani 1 1 d . . . . .
H16D H 0.903353 1.052706 0.558859 0.097 Uiso 1 1 calc R U . . .
H16E H 0.938734 0.986146 0.621126 0.097 Uiso 1 1 calc R U . . .
H16F H 0.862482 1.065391 0.617817 0.097 Uiso 1 1 calc R U . . .
C17B C 0.93517(16) 0.8526(2) 0.51705(13) 0.0377(5) Uani 1 1 d . . . . .
H17B H 0.968954 0.915438 0.525433 0.045 Uiso 1 1 calc R U . . .
C18B C 0.95560(15) 0.7672(2) 0.48245(12) 0.0353(5) Uani 1 1 d . . . . .
H18B H 1.003803 0.772593 0.466842 0.042 Uiso 1 1 calc R U . . .
C1C C 0.83404(17) 0.2759(2) 0.56386(13) 0.0394(6) Uani 1 1 d . . . . .
H1CA H 0.859330 0.234554 0.534783 0.059 Uiso 1 1 calc R U . . .
H1CB H 0.778601 0.249710 0.561132 0.059 Uiso 1 1 calc R U . . .
H1CC H 0.865131 0.265180 0.606162 0.059 Uiso 1 1 calc R U . . .
O1C O 0.83268(11) 0.38941(14) 0.54862(8) 0.0320(4) Uani 1 1 d . . . . .
H1C H 0.795599 0.420643 0.562231 0.048 Uiso 1 1 calc R U . . .
O1D O 1.0964(2) 0.1590(3) 0.20283(14) 0.0871(11) Uani 1 1 d . . . . .
Cl1D Cl 1.05201(4) 0.23572(7) 0.23219(3) 0.04715(17) Uani 1 1 d . . . . .
O2D O 1.09837(16) 0.3315(2) 0.24906(12) 0.0605(6) Uani 1 1 d . . . . .
O3D O 0.9778(3) 0.2619(5) 0.1965(3) 0.184(3) Uani 1 1 d . . . . .
O4D O 1.0412(2) 0.1839(2) 0.28840(16) 0.0877(11) Uani 1 1 d . . . . .
C1F C 0.5931(5) -0.0335(7) 0.6819(7) 0.240(7) Uani 1 1 d . . . . .
H1FA H 0.598060 -0.090098 0.651300 0.360 Uiso 1 1 calc R U . . .
H1FB H 0.539856 -0.038995 0.692729 0.360 Uiso 1 1 calc R U . . .
H1FC H 0.635354 -0.044053 0.719164 0.360 Uiso 1 1 calc R U . . .
O1F O 0.60166(19) 0.0705(3) 0.6567(2) 0.1022(13) Uani 1 1 d . . . . .
H1F H 0.650929 0.086857 0.662611 0.153 Uiso 1 1 calc R U . . .
C1E C 0.8034(3) 0.0895(4) 0.7371(2) 0.0849(14) Uani 1 1 d . . . . .
H1EA H 0.807215 0.009405 0.734809 0.127 Uiso 1 1 calc R U . . .
H1EB H 0.776851 0.109539 0.771058 0.127 Uiso 1 1 calc R U . . .
H1EC H 0.857730 0.121335 0.744554 0.127 Uiso 1 1 calc R U . . .
O1E O 0.75762(16) 0.1300(2) 0.68057(12) 0.0561(6) Uani 1 1 d D . . . .
H1E H 0.759(4) 0.1975(17) 0.680(3) 0.11(2) Uiso 1 1 d D . . . .
O1 O 0.6265(6) -0.0324(7) 0.5123(6) 0.095(3) Uani 0.34 1 d . . P A 1
O2 O 0.5656(7) -0.0428(9) 0.5380(7) 0.105(4) Uani 0.33 1 d . . P B 2
O3 O 0.6734(10) 0.0296(14) 0.5488(11) 0.174(8) Uani 0.33 1 d . . P C 3
Cl3 Cl 0.67171(3) 0.39945(5) 0.42728(3) 0.03271(13) Uani 1 1 d . . . D 3


_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
Cu1A O14A 1.9215(16) . ?
Cu1A N1A 1.9599(19) . ?
Cu1A N11A 1.9911(19) . ?
Cu1A O14B 2.0188(16) . ?
Cu1A O15B 2.4051(17) . ?
N1A C2A 1.321(3) . ?
N1A C9A 1.395(3) . ?
C2A N3A 1.350(3) . ?
C2A N10A 1.358(3) . ?
N3A C4A 1.390(3) . ?
N3A H3A 0.8800 . ?
C4A C5A 1.388(4) . ?
C4A C9A 1.394(4) . ?
C5A C6A 1.385(4) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.386(4) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.394(4) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.391(4) . ?
C8A H8A 0.9500 . ?
N10A N11A 1.390(3) . ?
N10A C101 1.442(3) . ?
C101 H10A 0.9800 . ?
C101 H10B 0.9800 . ?
C101 H10C 0.9800 . ?
N11A C12A 1.294(3) . ?
C12A C13A 1.433(3) . ?
C12A H12A 0.9500 . ?
C13A C18A 1.409(3) . ?
C13A C14A 1.426(3) . ?
O14A C14A 1.314(3) . ?
C14A C15A 1.410(3) . ?
O15A C15A 1.383(3) . ?
O15A C151 1.438(4) . ?
C15A C16A 1.395(3) . ?
C151 H15A 0.9800 . ?
C151 H15B 0.9800 . ?
C151 H15C 0.9800 . ?
C16A O16A 1.360(3) . ?
C16A C17A 1.392(4) . ?
O16A C161 1.428(3) . ?
C161 H16A 0.9800 . ?
C161 H16B 0.9800 . ?
C161 H16C 0.9800 . ?
C17A C18A 1.372(4) . ?
C17A H17A 0.9500 . ?
C18A H18A 0.9500 . ?
Cu1B O14B 1.9424(16) . ?
Cu1B N1B 1.952(2) . ?
Cu1B N11B 2.0015(19) . ?
Cu1B O1C 2.2212(17) . ?
Cu1B Cl3 2.2856(6) . ?
N1B C2B 1.324(3) . ?
N1B C9B 1.402(3) . ?
C2B N3B 1.348(3) . ?
C2B N10B 1.355(3) . ?
N3B C4B 1.394(4) . ?
N3B H3B 0.8800 . ?
C4B C5B 1.390(4) . ?
C4B C9B 1.398(4) . ?
C5B C6B 1.380(5) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.396(5) . ?
C6B H6B 0.9500 . ?
C7B C8B 1.398(4) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.388(4) . ?
C8B H8B 0.9500 . ?
N10B N11B 1.392(3) . ?
N10B C102 1.455(3) . ?
C102 H10D 0.9800 . ?
C102 H10E 0.9800 . ?
C102 H10F 0.9800 . ?
N11B C12B 1.284(3) . ?
C12B C13B 1.441(3) . ?
C12B H12B 0.9500 . ?
C13B C18B 1.401(3) . ?
C13B C14B 1.418(3) . ?
C14B O14B 1.337(3) . ?
C14B C15B 1.404(3) . ?
O15B C15B 1.383(3) . ?
O15B C152 1.449(3) . ?
C15B C16B 1.399(3) . ?
C152 H15D 0.9800 . ?
C152 H15E 0.9800 . ?
C152 H15F 0.9800 . ?
O16B C16B 1.356(3) . ?
O16B C162 1.426(4) . ?
C16B C17B 1.391(4) . ?
C162 H16D 0.9800 . ?
C162 H16E 0.9800 . ?
C162 H16F 0.9800 . ?
C17B C18B 1.376(4) . ?
C17B H17B 0.9500 . ?
C18B H18B 0.9500 . ?
C1C O1C 1.423(3) . ?
C1C H1CA 0.9800 . ?
C1C H1CB 0.9800 . ?
C1C H1CC 0.9800 . ?
O1C H1C 0.8400 . ?
O1D Cl1D 1.434(3) . ?
Cl1D O3D 1.373(4) . ?
Cl1D O2D 1.413(2) . ?
Cl1D O4D 1.436(3) . ?
C1F O1F 1.403(7) . ?
C1F H1FA 0.9800 . ?
C1F H1FB 0.9800 . ?
C1F H1FC 0.9800 . ?
O1F H1F 0.8400 . ?
C1E O1E 1.413(5) . ?
C1E H1EA 0.9800 . ?
C1E H1EB 0.9800 . ?
C1E H1EC 0.9800 . ?
O1E H1E 0.82(2) . ?

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
O14A Cu1A N1A 172.53(8) . . ?
O14A Cu1A N11A 91.87(7) . . ?
N1A Cu1A N11A 80.75(8) . . ?
O14A Cu1A O14B 91.84(7) . . ?
N1A Cu1A O14B 95.63(8) . . ?
N11A Cu1A O14B 168.91(8) . . ?
O14A Cu1A O15B 90.91(7) . . ?
N1A Cu1A O15B 90.87(7) . . ?
N11A Cu1A O15B 94.90(7) . . ?
O14B Cu1A O15B 74.59(6) . . ?
C2A N1A C9A 105.3(2) . . ?
C2A N1A Cu1A 112.30(15) . . ?
C9A N1A Cu1A 142.28(17) . . ?
N1A C2A N3A 113.8(2) . . ?
N1A C2A N10A 121.1(2) . . ?
N3A C2A N10A 125.1(2) . . ?
C2A N3A C4A 105.6(2) . . ?
C2A N3A H3A 127.2 . . ?
C4A N3A H3A 127.2 . . ?
C5A C4A N3A 130.2(3) . . ?
C5A C4A C9A 122.8(3) . . ?
N3A C4A C9A 106.9(2) . . ?
C6A C5A C4A 116.5(3) . . ?
C6A C5A H5A 121.7 . . ?
C4A C5A H5A 121.7 . . ?
C5A C6A C7A 121.4(2) . . ?
C5A C6A H6A 119.3 . . ?
C7A C6A H6A 119.3 . . ?
C6A C7A C8A 121.9(3) . . ?
C6A C7A H7A 119.0 . . ?
C8A C7A H7A 119.0 . . ?
C9A C8A C7A 117.2(3) . . ?
C9A C8A H8A 121.4 . . ?
C7A C8A H8A 121.4 . . ?
C8A C9A C4A 120.1(2) . . ?
C8A C9A N1A 131.5(2) . . ?
C4A C9A N1A 108.4(2) . . ?
C2A N10A N11A 111.7(2) . . ?
C2A N10A C101 125.4(2) . . ?
N11A N10A C101 122.6(2) . . ?
N10A C101 H10A 109.5 . . ?
N10A C101 H10B 109.5 . . ?
H10A C101 H10B 109.5 . . ?
N10A C101 H10C 109.5 . . ?
H10A C101 H10C 109.5 . . ?
H10B C101 H10C 109.5 . . ?
C12A N11A N10A 119.1(2) . . ?
C12A N11A Cu1A 127.40(17) . . ?
N10A N11A Cu1A 113.46(14) . . ?
N11A C12A C13A 123.7(2) . . ?
N11A C12A H12A 118.2 . . ?
C13A C12A H12A 118.2 . . ?
C18A C13A C14A 119.7(2) . . ?
C18A C13A C12A 116.2(2) . . ?
C14A C13A C12A 124.1(2) . . ?
C14A O14A Cu1A 127.67(15) . . ?
O14A C14A C15A 118.6(2) . . ?
O14A C14A C13A 124.7(2) . . ?
C15A C14A C13A 116.7(2) . . ?
C15A O15A C151 112.3(2) . . ?
O15A C15A C16A 118.9(2) . . ?
O15A C15A C14A 118.9(2) . . ?
C16A C15A C14A 122.2(2) . . ?
O15A C151 H15A 109.5 . . ?
O15A C151 H15B 109.5 . . ?
H15A C151 H15B 109.5 . . ?
O15A C151 H15C 109.5 . . ?
H15A C151 H15C 109.5 . . ?
H15B C151 H15C 109.5 . . ?
O16A C16A C17A 124.8(2) . . ?
O16A C16A C15A 114.9(2) . . ?
C17A C16A C15A 120.3(2) . . ?
C16A O16A C161 117.7(2) . . ?
O16A C161 H16A 109.5 . . ?
O16A C161 H16B 109.5 . . ?
H16A C161 H16B 109.5 . . ?
O16A C161 H16C 109.5 . . ?
H16A C161 H16C 109.5 . . ?
H16B C161 H16C 109.5 . . ?
C18A C17A C16A 118.8(2) . . ?
C18A C17A H17A 120.6 . . ?
C16A C17A H17A 120.6 . . ?
C17A C18A C13A 122.3(2) . . ?
C17A C18A H18A 118.9 . . ?
C13A C18A H18A 118.9 . . ?
O14B Cu1B N1B 171.71(8) . . ?
O14B Cu1B N11B 90.84(7) . . ?
N1B Cu1B N11B 80.88(8) . . ?
O14B Cu1B O1C 83.58(7) . . ?
N1B Cu1B O1C 98.96(8) . . ?
N11B Cu1B O1C 111.86(7) . . ?
O14B Cu1B Cl3 89.61(5) . . ?
N1B Cu1B Cl3 97.82(6) . . ?
N11B Cu1B Cl3 150.01(6) . . ?
O1C Cu1B Cl3 97.99(5) . . ?
C2B N1B C9B 105.9(2) . . ?
C2B N1B Cu1B 112.48(17) . . ?
C9B N1B Cu1B 141.52(18) . . ?
N1B C2B N3B 112.9(2) . . ?
N1B C2B N10B 121.2(2) . . ?
N3B C2B N10B 126.0(2) . . ?
C2B N3B C4B 106.7(2) . . ?
C2B N3B H3B 126.6 . . ?
C4B N3B H3B 126.6 . . ?
C5B C4B N3B 131.2(3) . . ?
C5B C4B C9B 122.5(3) . . ?
N3B C4B C9B 106.3(2) . . ?
C6B C5B C4B 116.7(3) . . ?
C6B C5B H5B 121.7 . . ?
C4B C5B H5B 121.7 . . ?
C5B C6B C7B 121.5(3) . . ?
C5B C6B H6B 119.2 . . ?
C7B C6B H6B 119.2 . . ?
C6B C7B C8B 121.7(3) . . ?
C6B C7B H7B 119.1 . . ?
C8B C7B H7B 119.1 . . ?
C9B C8B C7B 116.9(3) . . ?
C9B C8B H8B 121.6 . . ?
C7B C8B H8B 121.6 . . ?
C8B C9B C4B 120.7(3) . . ?
C8B C9B N1B 131.2(3) . . ?
C4B C9B N1B 108.1(2) . . ?
C2B N10B N11B 111.87(19) . . ?
C2B N10B C102 124.7(2) . . ?
N11B N10B C102 122.2(2) . . ?
N10B C102 H10D 109.5 . . ?
N10B C102 H10E 109.5 . . ?
H10D C102 H10E 109.5 . . ?
N10B C102 H10F 109.5 . . ?
H10D C102 H10F 109.5 . . ?
H10E C102 H10F 109.5 . . ?
C12B N11B N10B 119.5(2) . . ?
C12B N11B Cu1B 127.70(16) . . ?
N10B N11B Cu1B 112.80(15) . . ?
N11B C12B C13B 124.0(2) . . ?
N11B C12B H12B 118.0 . . ?
C13B C12B H12B 118.0 . . ?
C18B C13B C14B 118.8(2) . . ?
C18B C13B C12B 116.3(2) . . ?
C14B C13B C12B 124.9(2) . . ?
O14B C14B C15B 118.9(2) . . ?
O14B C14B C13B 122.9(2) . . ?
C15B C14B C13B 118.2(2) . . ?
C14B O14B Cu1B 127.87(14) . . ?
C14B O14B Cu1A 119.69(14) . . ?
Cu1B O14B Cu1A 112.44(8) . . ?
C15B O15B C152 114.28(19) . . ?
C15B O15B Cu1A 105.96(13) . . ?
C152 O15B Cu1A 113.92(15) . . ?
O15B C15B C16B 120.6(2) . . ?
O15B C15B C14B 117.9(2) . . ?
C16B C15B C14B 121.5(2) . . ?
O15B C152 H15D 109.5 . . ?
O15B C152 H15E 109.5 . . ?
H15D C152 H15E 109.5 . . ?
O15B C152 H15F 109.5 . . ?
H15D C152 H15F 109.5 . . ?
H15E C152 H15F 109.5 . . ?
C16B O16B C162 117.5(2) . . ?
O16B C16B C17B 124.6(2) . . ?
O16B C16B C15B 115.4(2) . . ?
C17B C16B C15B 120.0(2) . . ?
O16B C162 H16D 109.5 . . ?
O16B C162 H16E 109.5 . . ?
H16D C162 H16E 109.5 . . ?
O16B C162 H16F 109.5 . . ?
H16D C162 H16F 109.5 . . ?
H16E C162 H16F 109.5 . . ?
C18B C17B C16B 118.9(2) . . ?
C18B C17B H17B 120.5 . . ?
C16B C17B H17B 120.5 . . ?
C17B C18B C13B 122.6(2) . . ?
C17B C18B H18B 118.7 . . ?
C13B C18B H18B 118.7 . . ?
O1C C1C H1CA 109.5 . . ?
O1C C1C H1CB 109.5 . . ?
H1CA C1C H1CB 109.5 . . ?
O1C C1C H1CC 109.5 . . ?
H1CA C1C H1CC 109.5 . . ?
H1CB C1C H1CC 109.5 . . ?
C1C O1C Cu1B 118.06(15) . . ?
C1C O1C H1C 109.5 . . ?
Cu1B O1C H1C 103.4 . . ?
O3D Cl1D O2D 110.5(3) . . ?
O3D Cl1D O1D 113.2(4) . . ?
O2D Cl1D O1D 110.11(16) . . ?
O3D Cl1D O4D 109.4(3) . . ?
O2D Cl1D O4D 107.42(19) . . ?
O1D Cl1D O4D 105.93(18) . . ?
O1F C1F H1FA 109.5 . . ?
O1F C1F H1FB 109.5 . . ?
H1FA C1F H1FB 109.5 . . ?
O1F C1F H1FC 109.5 . . ?
H1FA C1F H1FC 109.5 . . ?
H1FB C1F H1FC 109.5 . . ?
C1F O1F H1F 109.5 . . ?
O1E C1E H1EA 109.5 . . ?
O1E C1E H1EB 109.5 . . ?
H1EA C1E H1EB 109.5 . . ?
O1E C1E H1EC 109.5 . . ?
H1EA C1E H1EC 109.5 . . ?
H1EB C1E H1EC 109.5 . . ?
C1E O1E H1E 111(4) . . ?

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
C9A N1A C2A N3A -1.8(3) . . . . ?
Cu1A N1A C2A N3A 175.15(18) . . . . ?
C9A N1A C2A N10A 177.9(2) . . . . ?
Cu1A N1A C2A N10A -5.1(3) . . . . ?
N1A C2A N3A C4A 1.9(3) . . . . ?
N10A C2A N3A C4A -177.8(3) . . . . ?
C2A N3A C4A C5A 178.5(3) . . . . ?
C2A N3A C4A C9A -1.1(3) . . . . ?
N3A C4A C5A C6A -179.3(3) . . . . ?
C9A C4A C5A C6A 0.3(4) . . . . ?
C4A C5A C6A C7A 0.6(5) . . . . ?
C5A C6A C7A C8A -0.7(5) . . . . ?
C6A C7A C8A C9A -0.1(4) . . . . ?
C7A C8A C9A C4A 1.0(4) . . . . ?
C7A C8A C9A N1A 179.1(3) . . . . ?
C5A C4A C9A C8A -1.1(4) . . . . ?
N3A C4A C9A C8A 178.6(2) . . . . ?
C5A C4A C9A N1A -179.6(3) . . . . ?
N3A C4A C9A N1A 0.1(3) . . . . ?
C2A N1A C9A C8A -177.3(3) . . . . ?
Cu1A N1A C9A C8A 7.3(5) . . . . ?
C2A N1A C9A C4A 1.0(3) . . . . ?
Cu1A N1A C9A C4A -174.4(2) . . . . ?
N1A C2A N10A N11A -1.0(4) . . . . ?
N3A C2A N10A N11A 178.6(2) . . . . ?
N1A C2A N10A C101 -173.9(3) . . . . ?
N3A C2A N10A C101 5.8(5) . . . . ?
C2A N10A N11A C12A -173.6(2) . . . . ?
C101 N10A N11A C12A -0.5(4) . . . . ?
C2A N10A N11A Cu1A 6.6(3) . . . . ?
C101 N10A N11A Cu1A 179.7(2) . . . . ?
N10A N11A C12A C13A -178.3(2) . . . . ?
Cu1A N11A C12A C13A 1.4(4) . . . . ?
N11A C12A C13A C18A -177.1(2) . . . . ?
N11A C12A C13A C14A 4.2(4) . . . . ?
Cu1A O14A C14A C15A 175.83(16) . . . . ?
Cu1A O14A C14A C13A -4.8(3) . . . . ?
C18A C13A C14A O14A 178.8(2) . . . . ?
C12A C13A C14A O14A -2.6(4) . . . . ?
C18A C13A C14A C15A -1.8(3) . . . . ?
C12A C13A C14A C15A 176.8(2) . . . . ?
C151 O15A C15A C16A -90.6(3) . . . . ?
C151 O15A C15A C14A 90.2(3) . . . . ?
O14A C14A C15A O15A -0.5(3) . . . . ?
C13A C14A C15A O15A -180.0(2) . . . . ?
O14A C14A C15A C16A -179.7(2) . . . . ?
C13A C14A C15A C16A 0.9(3) . . . . ?
O15A C15A C16A O16A 1.5(3) . . . . ?
C14A C15A C16A O16A -179.4(2) . . . . ?
O15A C15A C16A C17A -178.2(2) . . . . ?
C14A C15A C16A C17A 0.9(4) . . . . ?
C17A C16A O16A C161 -1.5(4) . . . . ?
C15A C16A O16A C161 178.8(3) . . . . ?
O16A C16A C17A C18A 178.4(2) . . . . ?
C15A C16A C17A C18A -1.9(4) . . . . ?
C16A C17A C18A C13A 1.0(4) . . . . ?
C14A C13A C18A C17A 0.9(4) . . . . ?
C12A C13A C18A C17A -177.8(2) . . . . ?
C9B N1B C2B N3B 0.3(3) . . . . ?
Cu1B N1B C2B N3B -176.81(16) . . . . ?
C9B N1B C2B N10B -179.4(2) . . . . ?
Cu1B N1B C2B N10B 3.5(3) . . . . ?
N1B C2B N3B C4B -1.1(3) . . . . ?
N10B C2B N3B C4B 178.6(2) . . . . ?
C2B N3B C4B C5B -176.8(3) . . . . ?
C2B N3B C4B C9B 1.3(3) . . . . ?
N3B C4B C5B C6B 178.9(3) . . . . ?
C9B C4B C5B C6B 1.0(4) . . . . ?
C4B C5B C6B C7B -0.3(5) . . . . ?
C5B C6B C7B C8B 0.0(5) . . . . ?
C6B C7B C8B C9B -0.2(5) . . . . ?
C7B C8B C9B C4B 0.9(4) . . . . ?
C7B C8B C9B N1B -177.3(3) . . . . ?
C5B C4B C9B C8B -1.4(4) . . . . ?
N3B C4B C9B C8B -179.7(2) . . . . ?
C5B C4B C9B N1B 177.2(2) . . . . ?
N3B C4B C9B N1B -1.1(3) . . . . ?
C2B N1B C9B C8B 178.9(3) . . . . ?
Cu1B N1B C9B C8B -5.3(5) . . . . ?
C2B N1B C9B C4B 0.5(3) . . . . ?
Cu1B N1B C9B C4B 176.3(2) . . . . ?
N1B C2B N10B N11B 3.5(3) . . . . ?
N3B C2B N10B N11B -176.1(2) . . . . ?
N1B C2B N10B C102 171.1(2) . . . . ?
N3B C2B N10B C102 -8.6(4) . . . . ?
C2B N10B N11B C12B 172.0(2) . . . . ?
C102 N10B N11B C12B 4.1(3) . . . . ?
C2B N10B N11B Cu1B -8.6(2) . . . . ?
C102 N10B N11B Cu1B -176.48(19) . . . . ?
N10B N11B C12B C13B -179.6(2) . . . . ?
Cu1B N11B C12B C13B 1.1(3) . . . . ?
N11B C12B C13B C18B 173.4(2) . . . . ?
N11B C12B C13B C14B -5.8(4) . . . . ?
C18B C13B C14B O14B 178.2(2) . . . . ?
C12B C13B C14B O14B -2.7(4) . . . . ?
C18B C13B C14B C15B -1.4(3) . . . . ?
C12B C13B C14B C15B 177.8(2) . . . . ?
C15B C14B O14B Cu1B -165.18(16) . . . . ?
C13B C14B O14B Cu1B 15.3(3) . . . . ?
C15B C14B O14B Cu1A 15.3(3) . . . . ?
C13B C14B O14B Cu1A -164.29(17) . . . . ?
C152 O15B C15B C16B -67.5(3) . . . . ?
Cu1A O15B C15B C16B 166.25(18) . . . . ?
C152 O15B C15B C14B 115.9(2) . . . . ?
Cu1A O15B C15B C14B -10.4(2) . . . . ?
O14B C14B C15B O15B -0.9(3) . . . . ?
C13B C14B C15B O15B 178.65(19) . . . . ?
O14B C14B C15B C16B -177.5(2) . . . . ?
C13B C14B C15B C16B 2.1(3) . . . . ?
C162 O16B C16B C17B -10.7(4) . . . . ?
C162 O16B C16B C15B 170.0(3) . . . . ?
O15B C15B C16B O16B 0.8(3) . . . . ?
C14B C15B C16B O16B 177.3(2) . . . . ?
O15B C15B C16B C17B -178.5(2) . . . . ?
C14B C15B C16B C17B -2.0(4) . . . . ?
O16B C16B C17B C18B -178.0(2) . . . . ?
C15B C16B C17B C18B 1.2(4) . . . . ?
C16B C17B C18B C13B -0.6(4) . . . . ?
C14B C13B C18B C17B 0.7(4) . . . . ?
C12B C13B C18B C17B -178.6(2) . . . . ?

_refine_diff_density_max         0.997
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.077



