# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_ft60-2s_a
_database_code_depnum_ccdc_archive 'CCDC 2191335'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Cl2 Cu N3 O2'
_chemical_formula_sum            'C17 H19 Cl2 Cu N3 O2'
_chemical_formula_weight         431.79

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   9.8712(10)
_cell_length_b                   13.0188(12)
_cell_length_c                   14.0060(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.771(10)
_cell_angle_gamma                90
_cell_volume                     1768.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4894
_cell_measurement_theta_min      2.1700
_cell_measurement_theta_max      27.5060

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.428
_exptl_crystal_size_mid          0.216
_exptl_crystal_size_min          0.157
_exptl_absorpt_coefficient_mu    1.553
_shelx_estimated_absorpt_T_min   0.556
_shelx_estimated_absorpt_T_max   0.792
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.637
_exptl_absorpt_correction_T_max  0.832
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)'
_exptl_absorpt_special_details   8.2564
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire2, large Be window'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 8.2564
_diffrn_reflns_number            11925
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.154
_diffrn_reflns_theta_max         28.559
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.898
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4054
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_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)+(0.0694P)²+0.8180P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4054
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0545
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1238
_refine_ls_wR_factor_gt          0.1132
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_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 0.15014(3) 0.74526(2) 0.67835(2) 0.03172(13) Uani 1 1 d . . . . .
Cl1 Cl -0.07758(8) 0.73446(6) 0.68218(7) 0.0485(2) Uani 1 1 d . . . . .
Cl2 Cl 0.19495(9) 0.86450(7) 0.79735(6) 0.0539(2) Uani 1 1 d . . . . .
N1 N 0.1620(2) 0.60377(16) 0.62263(16) 0.0292(5) Uani 1 1 d . . . . .
C2 C 0.0815(3) 0.5229(2) 0.6350(2) 0.0367(6) Uani 1 1 d . . . . .
H2A H 0.011973 0.532124 0.670799 0.044 Uiso 1 1 calc R U . . .
C3 C 0.0981(3) 0.4273(2) 0.5966(2) 0.0433(7) Uani 1 1 d . . . . .
H3A H 0.042915 0.372457 0.608127 0.052 Uiso 1 1 calc R U . . .
C5 C 0.2804(3) 0.4971(2) 0.5270(2) 0.0389(6) Uani 1 1 d . . . . .
H5A H 0.347998 0.489992 0.489249 0.047 Uiso 1 1 calc R U . . .
C4 C 0.1974(3) 0.4144(2) 0.5412(2) 0.0459(7) Uani 1 1 d . . . . .
H4A H 0.209219 0.350927 0.513318 0.055 Uiso 1 1 calc R U . . .
C6 C 0.2609(3) 0.58975(19) 0.56964(18) 0.0286(5) Uani 1 1 d . . . . .
C7 C 0.3489(3) 0.6827(2) 0.5565(2) 0.0311(6) Uani 1 1 d . . . . .
H7A H 0.309739 0.718585 0.496144 0.037 Uiso 1 1 calc R U . . .
N8 N 0.3541(2) 0.75386(15) 0.64216(17) 0.0295(5) Uani 1 1 d . . . . .
O9 O 0.4856(2) 0.65258(17) 0.55472(16) 0.0438(5) Uani 1 1 d . . . . .
C10 C 0.5477(3) 0.6417(3) 0.6547(3) 0.0469(8) Uani 1 1 d . . . . .
H10A H 0.647466 0.641936 0.662931 0.056 Uiso 1 1 calc R U . . .
H10B H 0.518627 0.578266 0.681175 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4972(3) 0.7343(2) 0.7041(2) 0.0378(7) Uani 1 1 d . . . . .
C12 C 0.4953(4) 0.7159(3) 0.8111(3) 0.0589(9) Uani 1 1 d . . . . .
H12A H 0.470180 0.779177 0.839922 0.071 Uiso 1 1 calc R U . . .
H12B H 0.425385 0.664969 0.816712 0.071 Uiso 1 1 calc R U . . .
C13 C 0.6341(4) 0.6790(3) 0.8674(3) 0.0736(12) Uani 1 1 d . . . . .
H13A H 0.627809 0.668472 0.934256 0.110 Uiso 1 1 calc R U . . .
H13B H 0.658534 0.615534 0.840048 0.110 Uiso 1 1 calc R U . . .
H13C H 0.703323 0.729728 0.863255 0.110 Uiso 1 1 calc R U . . .
C14 C 0.5774(3) 0.8335(3) 0.6841(3) 0.0533(9) Uani 1 1 d . . . . .
H14A H 0.588719 0.879414 0.739531 0.064 Uiso 1 1 calc R U . . .
H14B H 0.667776 0.815905 0.671266 0.064 Uiso 1 1 calc R U . . .
O15 O 0.4944(2) 0.88137(17) 0.59978(18) 0.0485(6) Uani 1 1 d . . . . .
C16 C 0.3602(3) 0.8639(2) 0.6151(2) 0.0359(6) Uani 1 1 d . . . . .
H16A H 0.346899 0.905126 0.671125 0.043 Uiso 1 1 calc R U . . .
C17 C 0.2460(3) 0.8910(2) 0.5308(2) 0.0361(6) Uani 1 1 d . . . . .
C18 C 0.2601(3) 0.9600(2) 0.4590(2) 0.0452(7) Uani 1 1 d . . . . .
H18A H 0.344385 0.991205 0.457495 0.054 Uiso 1 1 calc R U . . .
C19 C 0.1442(4) 0.9817(3) 0.3886(2) 0.0542(9) Uani 1 1 d . . . . .
H19A H 0.149510 1.029052 0.339714 0.065 Uiso 1 1 calc R U . . .
C20 C 0.0216(4) 0.9323(3) 0.3919(2) 0.0505(8) Uani 1 1 d . . . . .
H20A H -0.056465 0.944583 0.344721 0.061 Uiso 1 1 calc R U . . .
C21 C 0.0176(3) 0.8643(2) 0.4669(2) 0.0443(7) Uani 1 1 d . . . . .
H21A H -0.064864 0.830615 0.469089 0.053 Uiso 1 1 calc R U . . .
N22 N 0.1268(2) 0.84447(18) 0.53666(18) 0.0373(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.013(2) . ?
Cu1 N8 2.169(2) . ?
Cu1 Cl2 2.2601(8) . ?
Cu1 Cl1 2.2629(8) . ?
Cu1 N22 2.343(2) . ?
N1 C6 1.344(3) . ?
N1 C2 1.350(3) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.370(5) . ?
C3 H3A 0.9300 . ?
C5 C6 1.375(4) . ?
C5 C4 1.390(4) . ?
C5 H5A 0.9300 . ?
C4 H4A 0.9300 . ?
C6 C7 1.521(4) . ?
C7 O9 1.410(3) . ?
C7 N8 1.509(3) . ?
C7 H7A 0.9800 . ?
N8 C16 1.486(3) . ?
N8 C11 1.534(4) . ?
O9 C10 1.427(4) . ?
C10 C11 1.519(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.522(5) . ?
C11 C14 1.568(4) . ?
C12 C13 1.525(5) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O15 1.446(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
O15 C16 1.400(3) . ?
C16 C17 1.513(4) . ?
C16 H16A 0.9800 . ?
C17 N22 1.339(4) . ?
C17 C18 1.375(4) . ?
C18 C19 1.393(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.378(5) . ?
C19 H19A 0.9300 . ?
C20 C21 1.381(5) . ?
C20 H20A 0.9300 . ?
C21 N22 1.337(4) . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N8 80.37(8) . . ?
N1 Cu1 Cl2 153.78(7) . . ?
N8 Cu1 Cl2 94.27(6) . . ?
N1 Cu1 Cl1 94.73(7) . . ?
N8 Cu1 Cl1 168.05(7) . . ?
Cl2 Cu1 Cl1 94.80(3) . . ?
N1 Cu1 N22 100.35(9) . . ?
N8 Cu1 N22 73.87(8) . . ?
Cl2 Cu1 N22 102.75(7) . . ?
Cl1 Cu1 N22 96.52(6) . . ?
C6 N1 C2 118.1(2) . . ?
C6 N1 Cu1 116.06(17) . . ?
C2 N1 Cu1 125.84(18) . . ?
N1 C2 C3 122.6(3) . . ?
N1 C2 H2A 118.7 . . ?
C3 C2 H2A 118.7 . . ?
C4 C3 C2 118.8(3) . . ?
C4 C3 H3A 120.6 . . ?
C2 C3 H3A 120.6 . . ?
C6 C5 C4 118.9(3) . . ?
C6 C5 H5A 120.5 . . ?
C4 C5 H5A 120.5 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4A 120.4 . . ?
C5 C4 H4A 120.4 . . ?
N1 C6 C5 122.3(2) . . ?
N1 C6 C7 116.7(2) . . ?
C5 C6 C7 121.0(2) . . ?
O9 C7 N8 107.1(2) . . ?
O9 C7 C6 110.6(2) . . ?
N8 C7 C6 109.1(2) . . ?
O9 C7 H7A 110.0 . . ?
N8 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
C16 N8 C7 112.7(2) . . ?
C16 N8 C11 103.2(2) . . ?
C7 N8 C11 103.8(2) . . ?
C16 N8 Cu1 101.11(16) . . ?
C7 N8 Cu1 104.99(15) . . ?
C11 N8 Cu1 130.98(19) . . ?
C7 O9 C10 104.3(2) . . ?
O9 C10 C11 104.5(2) . . ?
O9 C10 H10A 110.9 . . ?
C11 C10 H10A 110.9 . . ?
O9 C10 H10B 110.9 . . ?
C11 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
C10 C11 C12 112.9(3) . . ?
C10 C11 N8 102.7(2) . . ?
C12 C11 N8 113.8(3) . . ?
C10 C11 C14 110.7(3) . . ?
C12 C11 C14 113.9(3) . . ?
N8 C11 C14 101.8(2) . . ?
C13 C12 C11 112.5(3) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O15 C14 C11 105.9(2) . . ?
O15 C14 H14A 110.6 . . ?
C11 C14 H14A 110.6 . . ?
O15 C14 H14B 110.6 . . ?
C11 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C16 O15 C14 102.3(2) . . ?
O15 C16 N8 106.3(2) . . ?
O15 C16 C17 115.5(2) . . ?
N8 C16 C17 111.4(2) . . ?
O15 C16 H16A 107.8 . . ?
N8 C16 H16A 107.8 . . ?
C17 C16 H16A 107.8 . . ?
N22 C17 C18 123.4(3) . . ?
N22 C17 C16 112.4(2) . . ?
C18 C17 C16 124.1(3) . . ?
C17 C18 C19 118.0(3) . . ?
C17 C18 H18A 121.0 . . ?
C19 C18 H18A 121.0 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
C19 C20 C21 118.3(3) . . ?
C19 C20 H20A 120.8 . . ?
C21 C20 H20A 120.8 . . ?
N22 C21 C20 123.1(3) . . ?
N22 C21 H21A 118.5 . . ?
C20 C21 H21A 118.5 . . ?
C21 N22 C17 117.8(3) . . ?
C21 N22 Cu1 131.5(2) . . ?
C17 N22 Cu1 110.65(18) . . ?

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
C6 N1 C2 C3 0.9(4) . . . . ?
Cu1 N1 C2 C3 -178.2(2) . . . . ?
N1 C2 C3 C4 -2.1(5) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C6 C5 C4 C3 0.4(5) . . . . ?
C2 N1 C6 C5 1.1(4) . . . . ?
Cu1 N1 C6 C5 -179.8(2) . . . . ?
C2 N1 C6 C7 179.5(2) . . . . ?
Cu1 N1 C6 C7 -1.3(3) . . . . ?
C4 C5 C6 N1 -1.7(4) . . . . ?
C4 C5 C6 C7 180.0(3) . . . . ?
N1 C6 C7 O9 145.0(2) . . . . ?
C5 C6 C7 O9 -36.5(3) . . . . ?
N1 C6 C7 N8 27.5(3) . . . . ?
C5 C6 C7 N8 -154.1(2) . . . . ?
O9 C7 N8 C16 94.3(3) . . . . ?
C6 C7 N8 C16 -146.0(2) . . . . ?
O9 C7 N8 C11 -16.7(3) . . . . ?
C6 C7 N8 C11 103.1(2) . . . . ?
O9 C7 N8 Cu1 -156.57(17) . . . . ?
C6 C7 N8 Cu1 -36.8(2) . . . . ?
N8 C7 O9 C10 37.3(3) . . . . ?
C6 C7 O9 C10 -81.5(3) . . . . ?
C7 O9 C10 C11 -42.9(3) . . . . ?
O9 C10 C11 C12 154.2(3) . . . . ?
O9 C10 C11 N8 31.2(3) . . . . ?
O9 C10 C11 C14 -76.8(3) . . . . ?
C16 N8 C11 C10 -126.6(2) . . . . ?
C7 N8 C11 C10 -8.8(3) . . . . ?
Cu1 N8 C11 C10 115.7(2) . . . . ?
C16 N8 C11 C12 111.0(3) . . . . ?
C7 N8 C11 C12 -131.2(3) . . . . ?
Cu1 N8 C11 C12 -6.7(4) . . . . ?
C16 N8 C11 C14 -12.0(3) . . . . ?
C7 N8 C11 C14 105.8(2) . . . . ?
Cu1 N8 C11 C14 -129.7(2) . . . . ?
C10 C11 C12 C13 53.7(4) . . . . ?
N8 C11 C12 C13 170.3(3) . . . . ?
C14 C11 C12 C13 -73.6(4) . . . . ?
C10 C11 C14 O15 93.7(3) . . . . ?
C12 C11 C14 O15 -137.8(3) . . . . ?
N8 C11 C14 O15 -14.9(3) . . . . ?
C11 C14 O15 C16 37.7(3) . . . . ?
C14 O15 C16 N8 -47.0(3) . . . . ?
C14 O15 C16 C17 -171.0(3) . . . . ?
C7 N8 C16 O15 -74.5(3) . . . . ?
C11 N8 C16 O15 36.8(3) . . . . ?
Cu1 N8 C16 O15 173.94(19) . . . . ?
C7 N8 C16 C17 52.1(3) . . . . ?
C11 N8 C16 C17 163.5(2) . . . . ?
Cu1 N8 C16 C17 -59.4(2) . . . . ?
O15 C16 C17 N22 160.4(2) . . . . ?
N8 C16 C17 N22 39.1(3) . . . . ?
O15 C16 C17 C18 -23.0(4) . . . . ?
N8 C16 C17 C18 -144.4(3) . . . . ?
N22 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C19 -176.6(3) . . . . ?
C17 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 1.4(5) . . . . ?
C19 C20 C21 N22 0.3(5) . . . . ?
C20 C21 N22 C17 -2.1(5) . . . . ?
C20 C21 N22 Cu1 174.5(2) . . . . ?
C18 C17 N22 C21 2.2(4) . . . . ?
C16 C17 N22 C21 178.8(3) . . . . ?
C18 C17 N22 Cu1 -175.1(2) . . . . ?
C16 C17 N22 Cu1 1.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A Cl1 0.93 2.79 3.297(3) 115.2 . yes
C3 H3A Cl2 0.93 2.90 3.585(3) 131.0 2_546 yes
C5 H5A O9 0.93 2.63 3.381(3) 138.6 3_666 yes
C10 H10A Cl1 0.97 2.94 3.842(3) 155.9 1_655 yes
C12 H12A Cl2 0.97 2.89 3.515(4) 122.9 . yes
C14 H14B Cl1 0.97 2.71 3.647(3) 163.6 1_655 yes
C16 H16A Cl2 0.98 2.58 3.276(3) 128.3 . yes
C18 H18A O15 0.93 2.53 3.401(4) 155.8 3_676 yes

_refine_diff_density_max         0.704
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_ft48
_database_code_depnum_ccdc_archive 'CCDC 2191338'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N6 O'
_chemical_formula_sum            'C19 H18 N6 O'
_chemical_formula_weight         346.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 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+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   5.6257(19)
_cell_length_b                   18.091(4)
_cell_length_c                   16.167(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1645.4(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(3)
_cell_measurement_reflns_used    6310
_cell_measurement_theta_min      3.3
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.952
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Kuma KM4 diffractometer with CCD camera'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14044
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.380
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             1985
_reflns_number_gt                1722
_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       'CrysAlis CCD; Oxford-Diffraction Poland, 2003'
_computing_cell_refinement       'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_data_reduction        'CrysAlis RED; Oxford-Diffraction Poland, 2003'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0698P)²+0.5665P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1985
_refine_ls_number_parameters     125
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1238
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.5664(2) 0.46630(7) 0.60720(7) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.3695(2) 0.41940(7) 0.60964(8) 0.0257(3) Uani 1 1 d . . . . .
H2 H 0.2373 0.4315 0.6436 0.031 Uiso 1 1 calc R U . . .
C3 C 0.3656(3) 0.35490(8) 0.56252(9) 0.0296(3) Uani 1 1 d . . . . .
H3 H 0.2311 0.3232 0.5648 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5572(3) 0.33649(8) 0.51210(8) 0.0311(3) Uani 1 1 d . . . . .
H4 H 0.5535 0.2926 0.4798 0.037 Uiso 1 1 calc R U . . .
C5 C 0.7538(3) 0.38284(8) 0.50950(8) 0.0311(3) Uani 1 1 d . . . . .
H5 H 0.8852 0.3708 0.4751 0.037 Uiso 1 1 calc R U . . .
C6 C 0.7590(2) 0.44697(8) 0.55711(8) 0.0267(3) Uani 1 1 d . . . . .
H6 H 0.8952 0.4780 0.5555 0.032 Uiso 1 1 calc R U . . .
C7 C 0.5689(2) 0.53588(7) 0.65405(8) 0.0222(3) Uani 1 1 d . . . . .
N1 N 0.7694(2) 0.57779(6) 0.66238(7) 0.0273(3) Uani 1 1 d . . . . .
N2 N 0.7175(2) 0.63787(7) 0.70481(8) 0.0286(3) Uani 1 1 d . . . . .
N3 N 0.4842(2) 0.63424(6) 0.72407(7) 0.0237(3) Uani 1 1 d . . . . .
C8 C 0.3853(2) 0.57214(7) 0.69352(8) 0.0227(3) Uani 1 1 d . . . . .
H8 H 0.2245 0.5567 0.6981 0.027 Uiso 1 1 calc R U . . .
C9 C 0.3708(3) 0.69322(7) 0.77108(8) 0.0258(3) Uani 1 1 d . . . . .
H9A H 0.4919 0.7184 0.8054 0.031 Uiso 1 1 calc R U . . .
H9B H 0.2510 0.6715 0.8088 0.031 Uiso 1 1 calc R U . . .
C10 C 0.2500 0.7500 0.71537(11) 0.0249(4) Uani 1 2 d S T P . .
H10 H 0.3667 0.7740 0.6803 0.030 Uiso 0.5 1 d R U P A 1
O1 O 0.1109(3) 0.72345(10) 0.65408(11) 0.0240(4) Uani 0.5 1 d . . P B 2
H1 H 0.0023 0.6973 0.6745 0.059(13) Uiso 0.5 1 calc R . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3961(19) . ?
C1 C6 1.3968(18) . ?
C1 C7 1.4692(18) . ?
C2 C3 1.394(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.3657(17) . ?
C7 C8 1.3797(18) . ?
N1 N2 1.3181(17) . ?
N2 N3 1.3505(17) . ?
N3 C8 1.3474(17) . ?
N3 C9 1.4569(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.5257(17) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O1 1.351(2) . ?
C10 O1 1.351(2) 2_565 ?
C10 C9 1.5257(17) 2_565 ?
C10 H10 0.9701 . ?
O1 H1 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
C2 C1 C6 118.66(12) . . ?
C2 C1 C7 120.90(12) . . ?
C6 C1 C7 120.40(12) . . ?
C3 C2 C1 120.38(12) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C4 C3 C2 120.56(14) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.34(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.20(13) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.85(13) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N1 C7 C8 107.97(12) . . ?
N1 C7 C1 122.29(12) . . ?
C8 C7 C1 129.70(12) . . ?
N2 N1 C7 109.03(11) . . ?
N1 N2 N3 107.17(11) . . ?
C8 N3 N2 110.92(11) . . ?
C8 N3 C9 128.40(12) . . ?
N2 N3 C9 120.68(11) . . ?
N3 C8 C7 104.90(12) . . ?
N3 C8 H8 127.5 . . ?
C7 C8 H8 127.5 . . ?
N3 C9 C10 112.35(11) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
O1 C10 O1 85.6(2) . 2_565 ?
O1 C10 C9 114.48(10) . 2_565 ?
O1 C10 C9 116.84(10) 2_565 2_565 ?
O1 C10 C9 116.84(10) . . ?
O1 C10 C9 114.48(10) 2_565 . ?
C9 C10 C9 107.66(15) 2_565 . ?
C9 C10 H10 110.2 2_565 . ?
C9 C10 H10 110.2 . . ?
C10 O1 H1 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 N1 0.84 2.54 3.264(2) 145.6 1_455
O1 H1 N2 0.84 1.99 2.823(2) 170.4 1_455

_refine_diff_density_max         0.238
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-2

####################################################################### 
# 
# 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_ft182-2b_a
_database_code_depnum_ccdc_archive 'CCDC 2191336'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 Br2 Cu N3 O2'
_chemical_formula_sum            'C17 H19 Br2 Cu N3 O2'
_chemical_formula_weight         520.71

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'
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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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                   10.09800(10)
_cell_length_b                   12.9658(2)
_cell_length_c                   14.2415(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.7850(10)
_cell_angle_gamma                90
_cell_volume                     1825.32(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    13590
_cell_measurement_theta_min      3.3720
_cell_measurement_theta_max      76.5280

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.895
_exptl_crystal_F_000             1028
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.455
_exptl_crystal_size_mid          0.157
_exptl_crystal_size_min          0.119
_exptl_absorpt_coefficient_mu    6.955
_shelx_estimated_absorpt_T_min   0.144
_shelx_estimated_absorpt_T_max   0.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.17969
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            20853
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.473
_diffrn_reflns_theta_max         77.324
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3764
_reflns_number_gt                3494
_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       'Oxford Diffraction CrysAlis'
_computing_cell_refinement       'Oxford Diffraction CrysAlis'
_computing_data_reduction        'Oxford Diffraction CrysAlis'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_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)+(0.0453P)²+1.5668P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3764
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0335
_refine_ls_wR_factor_ref         0.0902
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Br1 Br 1.07541(3) 0.26277(3) 0.31892(3) 0.05126(12) Uani 1 1 d . . . . .
Br2 Br 0.79553(3) 0.12594(3) 0.19920(2) 0.05235(12) Uani 1 1 d . . . . .
Cu1 Cu 0.83975(4) 0.25346(3) 0.32369(3) 0.03294(12) Uani 1 1 d . . . . .
N1 N 0.8306(2) 0.39659(17) 0.37684(15) 0.0333(4) Uani 1 1 d . . . . .
C2 C 0.9105(3) 0.4763(2) 0.3653(2) 0.0409(6) Uani 1 1 d . . . . .
H2A H 0.978193 0.466044 0.330743 0.049 Uiso 1 1 calc R U . . .
C3 C 0.8961(3) 0.5727(2) 0.4026(2) 0.0481(7) Uani 1 1 d . . . . .
H3A H 0.952160 0.626816 0.392694 0.058 Uiso 1 1 calc R U . . .
C4 C 0.7965(4) 0.5873(2) 0.4552(2) 0.0503(7) Uani 1 1 d . . . . .
H4A H 0.784869 0.651578 0.481321 0.060 Uiso 1 1 calc R U . . .
C5 C 0.7147(3) 0.5056(2) 0.4684(2) 0.0432(6) Uani 1 1 d . . . . .
H5A H 0.647944 0.513797 0.504121 0.052 Uiso 1 1 calc R U . . .
C6 C 0.7335(3) 0.4116(2) 0.42757(18) 0.0328(5) Uani 1 1 d . . . . .
C7 C 0.6480(3) 0.3195(2) 0.44148(19) 0.0341(5) Uani 1 1 d . . . . .
H7A H 0.688242 0.284010 0.501239 0.041 Uiso 1 1 calc R U . . .
O8 O 0.5149(2) 0.34974(18) 0.44388(17) 0.0503(5) Uani 1 1 d . . . . .
C9 C 0.4517(3) 0.3600(3) 0.3456(3) 0.0529(8) Uani 1 1 d . . . . .
H9A H 0.479439 0.423431 0.319049 0.063 Uiso 1 1 calc R U . . .
H9B H 0.353956 0.360010 0.337731 0.063 Uiso 1 1 calc R U . . .
C10 C 0.4991(3) 0.2664(2) 0.2968(2) 0.0428(6) Uani 1 1 d . . . . .
C11 C 0.4981(4) 0.2849(4) 0.1903(3) 0.0679(10) Uani 1 1 d . . . . .
H11A H 0.568523 0.334168 0.184875 0.081 Uiso 1 1 calc R U . . .
H11B H 0.519060 0.220714 0.161541 0.081 Uiso 1 1 calc R U . . .
C12 C 0.3636(5) 0.3252(4) 0.1349(3) 0.0846(13) Uani 1 1 d . . . . .
H12A H 0.368844 0.335333 0.069024 0.127 Uiso 1 1 calc R U . . .
H12B H 0.293746 0.276103 0.138723 0.127 Uiso 1 1 calc R U . . .
H12C H 0.343225 0.389594 0.162064 0.127 Uiso 1 1 calc R U . . .
C13 C 0.4222(3) 0.1678(3) 0.3172(3) 0.0624(9) Uani 1 1 d . . . . .
H13A H 0.333452 0.185574 0.328430 0.075 Uiso 1 1 calc R U . . .
H13B H 0.411111 0.120830 0.263109 0.075 Uiso 1 1 calc R U . . .
O14 O 0.5027(2) 0.12095(17) 0.40102(19) 0.0547(6) Uani 1 1 d . . . . .
C15 C 0.6337(3) 0.1368(2) 0.3860(2) 0.0386(6) Uani 1 1 d . . . . .
H15A H 0.644695 0.094467 0.331132 0.046 Uiso 1 1 calc R U . . .
N16 N 0.6401(2) 0.24701(16) 0.35787(16) 0.0321(4) Uani 1 1 d . . . . .
C17 C 0.7464(3) 0.1103(2) 0.4683(2) 0.0398(6) Uani 1 1 d . . . . .
C18 C 0.7337(4) 0.0429(2) 0.5409(2) 0.0524(7) Uani 1 1 d . . . . .
H18A H 0.650859 0.012808 0.543404 0.063 Uiso 1 1 calc R U . . .
C19 C 0.8481(4) 0.0216(3) 0.6099(2) 0.0613(9) Uani 1 1 d . . . . .
H19A H 0.843519 -0.024371 0.659290 0.074 Uiso 1 1 calc R U . . .
C20 C 0.9688(4) 0.0685(3) 0.6051(2) 0.0568(8) Uani 1 1 d . . . . .
H20A H 1.046269 0.056027 0.651627 0.068 Uiso 1 1 calc R U . . .
C21 C 0.9720(3) 0.1344(2) 0.5300(2) 0.0479(7) Uani 1 1 d . . . . .
H21A H 1.053581 0.166074 0.526649 0.057 Uiso 1 1 calc R U . . .
N22 N 0.8638(2) 0.15502(19) 0.46174(17) 0.0397(5) 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
Br1 Cu1 2.3976(5) . ?
Br2 Cu1 2.3986(5) . ?
Cu1 N1 2.013(2) . ?
Cu1 N16 2.170(2) . ?
Cu1 N22 2.315(2) . ?
N1 C2 1.341(4) . ?
N1 C6 1.346(3) . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.384(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4A 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5A 0.9300 . ?
C6 C7 1.510(4) . ?
C7 O8 1.407(3) . ?
C7 N16 1.507(3) . ?
C7 H7A 0.9800 . ?
O8 C9 1.422(4) . ?
C9 C10 1.524(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N16 1.530(3) . ?
C10 C11 1.534(5) . ?
C10 C13 1.554(5) . ?
C11 C12 1.517(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 O14 1.435(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
O14 C15 1.397(3) . ?
C15 N16 1.489(3) . ?
C15 C17 1.497(4) . ?
C15 H15A 0.9800 . ?
C17 N22 1.340(4) . ?
C17 C18 1.380(4) . ?
C18 C19 1.383(5) . ?
C18 H18A 0.9300 . ?
C19 C20 1.377(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(5) . ?
C20 H20A 0.9300 . ?
C21 N22 1.333(4) . ?
C21 H21A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 N16 80.51(8) . . ?
N1 Cu1 N22 101.18(9) . . ?
N16 Cu1 N22 74.30(8) . . ?
N1 Cu1 Br1 94.95(6) . . ?
N16 Cu1 Br1 168.89(6) . . ?
N22 Cu1 Br1 96.85(6) . . ?
N1 Cu1 Br2 153.81(6) . . ?
N16 Cu1 Br2 95.63(6) . . ?
N22 Cu1 Br2 102.66(6) . . ?
Br1 Cu1 Br2 92.851(17) . . ?
C2 N1 C6 118.5(2) . . ?
C2 N1 Cu1 126.09(18) . . ?
C6 N1 Cu1 115.44(17) . . ?
N1 C2 C3 122.6(3) . . ?
N1 C2 H2A 118.7 . . ?
C3 C2 H2A 118.7 . . ?
C2 C3 C4 118.6(3) . . ?
C2 C3 H3A 120.7 . . ?
C4 C3 H3A 120.7 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4A 120.3 . . ?
C3 C4 H4A 120.3 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5A 120.6 . . ?
C6 C5 H5A 120.6 . . ?
N1 C6 C5 122.1(2) . . ?
N1 C6 C7 117.1(2) . . ?
C5 C6 C7 120.8(2) . . ?
O8 C7 N16 107.2(2) . . ?
O8 C7 C6 111.0(2) . . ?
N16 C7 C6 109.2(2) . . ?
O8 C7 H7A 109.8 . . ?
N16 C7 H7A 109.8 . . ?
C6 C7 H7A 109.8 . . ?
C7 O8 C9 104.0(2) . . ?
O8 C9 C10 104.7(2) . . ?
O8 C9 H9A 110.8 . . ?
C10 C9 H9A 110.8 . . ?
O8 C9 H9B 110.8 . . ?
C10 C9 H9B 110.8 . . ?
H9A C9 H9B 108.9 . . ?
C9 C10 N16 102.4(2) . . ?
C9 C10 C11 112.8(3) . . ?
N16 C10 C11 113.9(3) . . ?
C9 C10 C13 110.8(3) . . ?
N16 C10 C13 101.6(2) . . ?
C11 C10 C13 114.3(3) . . ?
C12 C11 C10 113.1(3) . . ?
C12 C11 H11A 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O14 C13 C10 106.5(2) . . ?
O14 C13 H13A 110.4 . . ?
C10 C13 H13A 110.4 . . ?
O14 C13 H13B 110.4 . . ?
C10 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C15 O14 C13 101.8(2) . . ?
O14 C15 N16 106.0(2) . . ?
O14 C15 C17 116.0(2) . . ?
N16 C15 C17 111.3(2) . . ?
O14 C15 H15A 107.7 . . ?
N16 C15 H15A 107.7 . . ?
C17 C15 H15A 107.7 . . ?
C15 N16 C7 112.6(2) . . ?
C15 N16 C10 103.0(2) . . ?
C7 N16 C10 103.9(2) . . ?
C15 N16 Cu1 100.98(15) . . ?
C7 N16 Cu1 104.57(15) . . ?
C10 N16 Cu1 131.70(18) . . ?
N22 C17 C18 123.0(3) . . ?
N22 C17 C15 112.9(2) . . ?
C18 C17 C15 124.0(3) . . ?
C17 C18 C19 117.8(3) . . ?
C17 C18 H18A 121.1 . . ?
C19 C18 H18A 121.1 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19A 120.1 . . ?
C18 C19 H19A 120.1 . . ?
C21 C20 C19 118.4(3) . . ?
C21 C20 H20A 120.8 . . ?
C19 C20 H20A 120.8 . . ?
N22 C21 C20 123.1(3) . . ?
N22 C21 H21A 118.5 . . ?
C20 C21 H21A 118.5 . . ?
C21 N22 C17 117.9(3) . . ?
C21 N22 Cu1 131.2(2) . . ?
C17 N22 Cu1 110.89(18) . . ?

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
C6 N1 C2 C3 -0.6(4) . . . . ?
Cu1 N1 C2 C3 178.8(2) . . . . ?
N1 C2 C3 C4 0.9(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C2 N1 C6 C5 -0.5(4) . . . . ?
Cu1 N1 C6 C5 -179.9(2) . . . . ?
C2 N1 C6 C7 -178.4(2) . . . . ?
Cu1 N1 C6 C7 2.3(3) . . . . ?
C4 C5 C6 N1 1.2(4) . . . . ?
C4 C5 C6 C7 178.9(3) . . . . ?
N1 C6 C7 O8 -146.7(2) . . . . ?
C5 C6 C7 O8 35.5(3) . . . . ?
N1 C6 C7 N16 -28.7(3) . . . . ?
C5 C6 C7 N16 153.5(2) . . . . ?
N16 C7 O8 C9 -37.8(3) . . . . ?
C6 C7 O8 C9 81.4(3) . . . . ?
C7 O8 C9 C10 43.1(3) . . . . ?
O8 C9 C10 N16 -31.1(3) . . . . ?
O8 C9 C10 C11 -153.9(3) . . . . ?
O8 C9 C10 C13 76.6(3) . . . . ?
C9 C10 C11 C12 -52.1(5) . . . . ?
N16 C10 C11 C12 -168.3(3) . . . . ?
C13 C10 C11 C12 75.5(4) . . . . ?
C9 C10 C13 O14 -92.2(3) . . . . ?
N16 C10 C13 O14 16.0(3) . . . . ?
C11 C10 C13 O14 139.1(3) . . . . ?
C10 C13 O14 C15 -38.7(3) . . . . ?
C13 O14 C15 N16 47.3(3) . . . . ?
C13 O14 C15 C17 171.4(3) . . . . ?
O14 C15 N16 C7 74.6(3) . . . . ?
C17 C15 N16 C7 -52.5(3) . . . . ?
O14 C15 N16 C10 -36.7(3) . . . . ?
C17 C15 N16 C10 -163.7(2) . . . . ?
O14 C15 N16 Cu1 -174.44(18) . . . . ?
C17 C15 N16 Cu1 58.5(2) . . . . ?
O8 C7 N16 C15 -93.4(3) . . . . ?
C6 C7 N16 C15 146.2(2) . . . . ?
O8 C7 N16 C10 17.3(3) . . . . ?
C6 C7 N16 C10 -103.1(2) . . . . ?
O8 C7 N16 Cu1 157.82(17) . . . . ?
C6 C7 N16 Cu1 37.5(2) . . . . ?
C9 C10 N16 C15 125.9(3) . . . . ?
C11 C10 N16 C15 -112.0(3) . . . . ?
C13 C10 N16 C15 11.4(3) . . . . ?
C9 C10 N16 C7 8.3(3) . . . . ?
C11 C10 N16 C7 130.4(3) . . . . ?
C13 C10 N16 C7 -106.2(3) . . . . ?
C9 C10 N16 Cu1 -116.2(2) . . . . ?
C11 C10 N16 Cu1 5.8(4) . . . . ?
C13 C10 N16 Cu1 129.2(2) . . . . ?
O14 C15 C17 N22 -160.9(2) . . . . ?
N16 C15 C17 N22 -39.5(3) . . . . ?
O14 C15 C17 C18 22.3(4) . . . . ?
N16 C15 C17 C18 143.7(3) . . . . ?
N22 C17 C18 C19 0.3(5) . . . . ?
C15 C17 C18 C19 176.8(3) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 N22 0.1(5) . . . . ?
C20 C21 N22 C17 1.1(5) . . . . ?
C20 C21 N22 Cu1 -176.1(2) . . . . ?
C18 C17 N22 C21 -1.4(4) . . . . ?
C15 C17 N22 C21 -178.2(3) . . . . ?
C18 C17 N22 Cu1 176.4(2) . . . . ?
C15 C17 N22 Cu1 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A Br1 0.93 2.83 3.365(3) 117.8 . yes
C3 H3A Br2 0.93 3.09 3.757(3) 129.9 2_755 yes
C5 H5A O8 0.93 2.62 3.411(3) 142.9 3_666 yes
C7 H7A Br2 0.98 3.04 3.736(3) 129.1 4_566 yes
C9 H9B Br1 0.97 3.04 3.947(3) 155.5 1_455 yes
C11 H11B Br2 0.97 3.00 3.623(4) 123.5 . yes
C13 H13A Br1 0.97 2.77 3.717(4) 165.9 1_455 yes
C15 H15A Br2 0.98 2.68 3.398(3) 130.3 . yes
C18 H18A O14 0.93 2.56 3.421(4) 154.6 3_656 yes

_refine_diff_density_max         0.607
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_ftcat48b_a
_database_code_depnum_ccdc_archive 'CCDC 2191339'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 Cl N3 O'
_chemical_formula_sum            'C11 H12 Cl N3 O'
_chemical_formula_weight         237.69

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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   28.110(3)
_cell_length_b                   10.0413(9)
_cell_length_c                   8.0483(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2271.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1459
_cell_measurement_theta_min      3.1040
_cell_measurement_theta_max      69.1410

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.048
_exptl_crystal_size_mid          0.016
_exptl_crystal_size_min          0.013
_exptl_absorpt_coefficient_mu    2.838
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            13017
_diffrn_reflns_av_unetI/netI     0.0827
_diffrn_reflns_av_R_equivalents  0.1503
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.144
_diffrn_reflns_theta_max         80.315
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2430
_reflns_number_gt                1318
_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0062(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2430
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.1090
_refine_ls_wR_factor_ref         0.3453
_refine_ls_wR_factor_gt          0.2916
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      1.128
_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
C1 C 0.3926(2) 0.2844(5) 0.5961(7) 0.0433(14) Uani 1 1 d . . . . .
H1A H 0.376348 0.223565 0.666528 0.052 Uiso 1 1 calc R U . . .
C2 C 0.4397(2) 0.2599(6) 0.5504(8) 0.0494(15) Uani 1 1 d . . . . .
H2A H 0.455581 0.182533 0.589777 0.059 Uiso 1 1 calc R U . . .
C3 C 0.4630(2) 0.3479(7) 0.4482(8) 0.0515(15) Uani 1 1 d . . . . .
H3A H 0.495213 0.331701 0.418300 0.062 Uiso 1 1 calc R U . . .
C4 C 0.4401(2) 0.4598(6) 0.3888(7) 0.0461(14) Uani 1 1 d . . . . .
H4A H 0.456284 0.518839 0.316059 0.055 Uiso 1 1 calc R U . . .
C5 C 0.3937(2) 0.4862(6) 0.4342(6) 0.0406(13) Uani 1 1 d . . . . .
H5A H 0.378386 0.564294 0.394496 0.049 Uiso 1 1 calc R U . . .
C6 C 0.3692(2) 0.3984(5) 0.5385(6) 0.0363(12) Uani 1 1 d . . . . .
C7 C 0.3203(2) 0.4252(5) 0.5881(6) 0.0359(12) Uani 1 1 d . . . . .
N8 N 0.30016(18) 0.5481(4) 0.5766(5) 0.0419(11) Uani 1 1 d . . . . .
N9 N 0.25571(18) 0.5426(4) 0.6327(6) 0.0425(12) Uani 1 1 d . . . . .
N10 N 0.24824(17) 0.4172(4) 0.6811(5) 0.0364(10) Uani 1 1 d . . . . .
C11 C 0.2870(2) 0.3418(5) 0.6557(6) 0.0371(12) Uani 1 1 d . . . . .
H11A H 0.290659 0.249691 0.679772 0.044 Uiso 1 1 calc R U . . .
C12 C 0.2022(2) 0.3798(5) 0.7460(6) 0.0407(13) Uani 1 1 d . . . . .
H12A H 0.193117 0.441389 0.836682 0.049 Uiso 1 1 calc R U . . .
H12B H 0.203839 0.288624 0.792526 0.049 Uiso 1 1 calc R U . . .
C13 C 0.1646(2) 0.3847(6) 0.6080(6) 0.0436(14) Uani 1 1 d . . . . .
H13A H 0.161601 0.479934 0.572982 0.052 Uiso 1 1 calc R U . . .
O14 O 0.17873(14) 0.3127(4) 0.4682(4) 0.0411(10) Uani 1 1 d . . . . .
H14A H 0.157521 0.317617 0.394951 0.062 Uiso 1 1 calc R U . . .
C15 C 0.1174(2) 0.3436(7) 0.6759(8) 0.0561(16) Uani 1 1 d . . . . .
H15A H 0.110156 0.395430 0.777450 0.067 Uiso 1 1 calc R U . . .
H15B H 0.118117 0.247963 0.705856 0.067 Uiso 1 1 calc R U . . .
Cl16 Cl 0.07175(8) 0.3729(2) 0.5199(3) 0.0793(8) 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
C1 C2 1.397(9) . ?
C1 C6 1.398(8) . ?
C1 H1A 0.9500 . ?
C2 C3 1.373(9) . ?
C2 H2A 0.9500 . ?
C3 C4 1.382(9) . ?
C3 H3A 0.9500 . ?
C4 C5 1.378(8) . ?
C4 H4A 0.9500 . ?
C5 C6 1.399(7) . ?
C5 H5A 0.9500 . ?
C6 C7 1.458(8) . ?
C7 N8 1.361(6) . ?
C7 C11 1.368(7) . ?
N8 N9 1.330(7) . ?
N9 N10 1.335(6) . ?
N10 C11 1.343(7) . ?
N10 C12 1.445(7) . ?
C11 H11A 0.9500 . ?
C12 C13 1.535(8) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.395(6) . ?
C13 C15 1.493(9) . ?
C13 H13A 1.0000 . ?
O14 H14A 0.8400 . ?
C15 Cl16 1.820(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?

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 C1 C6 120.1(5) . . ?
C2 C1 H1A 119.9 . . ?
C6 C1 H1A 119.9 . . ?
C3 C2 C1 119.8(6) . . ?
C3 C2 H2A 120.1 . . ?
C1 C2 H2A 120.1 . . ?
C2 C3 C4 120.5(6) . . ?
C2 C3 H3A 119.8 . . ?
C4 C3 H3A 119.8 . . ?
C5 C4 C3 120.4(6) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5A 119.9 . . ?
C6 C5 H5A 119.9 . . ?
C1 C6 C5 119.0(5) . . ?
C1 C6 C7 120.2(5) . . ?
C5 C6 C7 120.8(5) . . ?
N8 C7 C11 107.4(5) . . ?
N8 C7 C6 122.8(5) . . ?
C11 C7 C6 129.8(5) . . ?
N9 N8 C7 109.2(4) . . ?
N8 N9 N10 106.6(4) . . ?
N9 N10 C11 111.1(4) . . ?
N9 N10 C12 119.4(5) . . ?
C11 N10 C12 129.5(4) . . ?
N10 C11 C7 105.7(4) . . ?
N10 C11 H11A 127.2 . . ?
C7 C11 H11A 127.2 . . ?
N10 C12 C13 110.3(4) . . ?
N10 C12 H12A 109.6 . . ?
C13 C12 H12A 109.6 . . ?
N10 C12 H12B 109.6 . . ?
C13 C12 H12B 109.6 . . ?
H12A C12 H12B 108.1 . . ?
O14 C13 C15 113.9(5) . . ?
O14 C13 C12 111.8(5) . . ?
C15 C13 C12 109.7(5) . . ?
O14 C13 H13A 107.0 . . ?
C15 C13 H13A 107.0 . . ?
C12 C13 H13A 107.0 . . ?
C13 O14 H14A 109.5 . . ?
C13 C15 Cl16 109.2(4) . . ?
C13 C15 H15A 109.8 . . ?
Cl16 C15 H15A 109.8 . . ?
C13 C15 H15B 109.8 . . ?
Cl16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.3 . . ?

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
C6 C1 C2 C3 -0.2(9) . . . . ?
C1 C2 C3 C4 -0.8(10) . . . . ?
C2 C3 C4 C5 1.5(9) . . . . ?
C3 C4 C5 C6 -1.3(8) . . . . ?
C2 C1 C6 C5 0.4(8) . . . . ?
C2 C1 C6 C7 -179.1(5) . . . . ?
C4 C5 C6 C1 0.3(8) . . . . ?
C4 C5 C6 C7 179.8(5) . . . . ?
C1 C6 C7 N8 161.1(5) . . . . ?
C5 C6 C7 N8 -18.4(7) . . . . ?
C1 C6 C7 C11 -16.8(8) . . . . ?
C5 C6 C7 C11 163.7(5) . . . . ?
C11 C7 N8 N9 -0.8(6) . . . . ?
C6 C7 N8 N9 -179.1(4) . . . . ?
C7 N8 N9 N10 0.8(6) . . . . ?
N8 N9 N10 C11 -0.5(6) . . . . ?
N8 N9 N10 C12 -179.0(4) . . . . ?
N9 N10 C11 C7 0.0(6) . . . . ?
C12 N10 C11 C7 178.3(5) . . . . ?
N8 C7 C11 N10 0.5(5) . . . . ?
C6 C7 C11 N10 178.6(5) . . . . ?
N9 N10 C12 C13 68.1(6) . . . . ?
C11 N10 C12 C13 -110.0(6) . . . . ?
N10 C12 C13 O14 51.7(6) . . . . ?
N10 C12 C13 C15 179.0(5) . . . . ?
O14 C13 C15 Cl16 -62.1(6) . . . . ?
C12 C13 C15 Cl16 171.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11A N9 0.95 2.48 3.241(7) 136.7 8_655 yes
C11 H11A O14 0.95 2.55 3.107(6) 117.4 2 yes
O14 H14A Cl16 0.84 2.67 3.096(4) 112.9 . yes

_refine_diff_density_max         1.045
_refine_diff_density_min         -0.749
_refine_diff_density_rms         0.161

####################################################################### 
# 
# 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_ftcat48d_a
_database_code_depnum_ccdc_archive 'CCDC 2191340'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 N3 O3'
_chemical_formula_sum            'C13 H15 N3 O3'
_chemical_formula_weight         261.28

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'
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           7
_space_group_name_H-M_alt        'P n'
_space_group_name_Hall           'P -2yac'

_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, z+1/2'

_cell_length_a                   4.6463(3)
_cell_length_b                   13.9998(9)
_cell_length_c                   9.8490(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.320(7)
_cell_angle_gamma                90
_cell_volume                     636.76(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2562
_cell_measurement_theta_min      5.4640
_cell_measurement_theta_max      76.4390

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             276
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.019
_exptl_absorpt_coefficient_mu    0.820
_shelx_estimated_absorpt_T_min   0.873
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72625
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.41.119a (Rigaku Oxford Diffraction, 2021)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            3493
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.157
_diffrn_reflns_theta_max         77.524
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.924
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.924
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.540
_diffrn_reflns_point_group_measured_fraction_full 0.584
_reflns_number_total             1462
_reflns_number_gt                1418
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.162
_reflns_Friedel_fraction_max     0.152
_reflns_Friedel_fraction_full    0.171

_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 1.171.41.119a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.119a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  'CIFTAB (Sheldrick, 2014)'
_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)+(0.1301P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.1(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1462
_refine_ls_number_parameters     173
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1492
_refine_ls_wR_factor_gt          0.1484
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_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
C1 C 0.7748(8) 0.8553(3) 0.3456(4) 0.0315(8) Uani 1 1 d . . . . .
H1A H 0.717615 0.827078 0.259091 0.038 Uiso 1 1 calc R U . . .
C2 C 0.9727(9) 0.9291(3) 0.3558(5) 0.0378(9) Uani 1 1 d . . . . .
H2A H 1.049974 0.951652 0.276297 0.045 Uiso 1 1 calc R U . . .
C3 C 1.0594(9) 0.9707(3) 0.4818(6) 0.0423(11) Uani 1 1 d . . . . .
H3A H 1.197569 1.021016 0.489135 0.051 Uiso 1 1 calc R U . . .
C4 C 0.9424(9) 0.9382(3) 0.5965(5) 0.0392(10) Uani 1 1 d . . . . .
H4A H 1.000144 0.966819 0.682627 0.047 Uiso 1 1 calc R U . . .
C5 C 0.7418(8) 0.8644(3) 0.5876(4) 0.0308(8) Uani 1 1 d . . . . .
H5A H 0.661879 0.842908 0.666902 0.037 Uiso 1 1 calc R U . . .
C6 C 0.6582(7) 0.8217(2) 0.4607(3) 0.0240(7) Uani 1 1 d . . . . .
C7 C 0.4477(7) 0.7433(2) 0.4493(3) 0.0202(6) Uani 1 1 d . . . . .
N8 N 0.3636(6) 0.6994(2) 0.3271(3) 0.0233(6) Uani 1 1 d . . . . .
N9 N 0.1724(6) 0.6329(2) 0.3455(3) 0.0230(6) Uani 1 1 d . . . . .
N10 N 0.1353(6) 0.63307(19) 0.4802(3) 0.0197(6) Uani 1 1 d . . . . .
C11 C 0.3017(7) 0.7004(2) 0.5477(3) 0.0204(6) Uani 1 1 d . . . . .
H11A H 0.315519 0.715151 0.642337 0.025 Uiso 1 1 calc R U . . .
C12 C -0.0556(7) 0.5634(2) 0.5343(3) 0.0218(7) Uani 1 1 d . . . . .
H12A H -0.215643 0.547839 0.462927 0.026 Uiso 1 1 calc R U . . .
H12B H -0.141409 0.592032 0.612514 0.026 Uiso 1 1 calc R U . . .
C13 C 0.1016(7) 0.4716(2) 0.5811(3) 0.0220(7) Uani 1 1 d . . . . .
H13A H -0.032743 0.430462 0.628141 0.026 Uiso 1 1 calc R U . . .
O14 O 0.3383(6) 0.49836(17) 0.6767(2) 0.0264(6) Uani 1 1 d . . . . .
H14A H 0.429215 0.449247 0.705610 0.040 Uiso 1 1 calc R U . . .
C15 C 0.2010(7) 0.4166(2) 0.4624(3) 0.0225(7) Uani 1 1 d . . . . .
H15A H 0.033743 0.399249 0.395832 0.027 Uiso 1 1 calc R U . . .
H15B H 0.338130 0.455163 0.415102 0.027 Uiso 1 1 calc R U . . .
O16 O 0.3422(6) 0.33135(16) 0.5216(2) 0.0278(6) Uani 1 1 d . . . . .
C17 C 0.4943(8) 0.2804(2) 0.4405(3) 0.0242(7) Uani 1 1 d . . . . .
O18 O 0.5045(8) 0.2999(2) 0.3222(3) 0.0479(9) Uani 1 1 d . . . . .
C19 C 0.6469(9) 0.1980(3) 0.5135(4) 0.0333(8) Uani 1 1 d . . . . .
H19A H 0.504975 0.156766 0.551288 0.050 Uiso 1 1 calc R U . . .
H19B H 0.785955 0.221887 0.587699 0.050 Uiso 1 1 calc R U . . .
H19C H 0.749701 0.161246 0.449131 0.050 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
C1 C2 1.380(6) . ?
C1 C6 1.391(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.390(7) . ?
C2 H2A 0.9500 . ?
C3 C4 1.383(7) . ?
C3 H3A 0.9500 . ?
C4 C5 1.388(6) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(5) . ?
C5 H5A 0.9500 . ?
C6 C7 1.467(5) . ?
C7 N8 1.369(4) . ?
C7 C11 1.380(4) . ?
N8 N9 1.313(4) . ?
N9 N10 1.356(4) . ?
N10 C11 1.347(4) . ?
N10 C12 1.458(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.524(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 O14 1.417(4) . ?
C13 C15 1.515(4) . ?
C13 H13A 1.0000 . ?
O14 H14A 0.8400 . ?
C15 O16 1.452(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
O16 C17 1.330(4) . ?
C17 O18 1.203(4) . ?
C17 C19 1.496(5) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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
C2 C1 C6 120.7(4) . . ?
C2 C1 H1A 119.7 . . ?
C6 C1 H1A 119.7 . . ?
C1 C2 C3 120.3(4) . . ?
C1 C2 H2A 119.9 . . ?
C3 C2 H2A 119.9 . . ?
C4 C3 C2 119.3(4) . . ?
C4 C3 H3A 120.3 . . ?
C2 C3 H3A 120.3 . . ?
C3 C4 C5 121.0(4) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C4 C5 C6 119.5(4) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 119.2(3) . . ?
C1 C6 C7 120.4(3) . . ?
C5 C6 C7 120.3(3) . . ?
N8 C7 C11 107.9(3) . . ?
N8 C7 C6 121.8(3) . . ?
C11 C7 C6 130.3(3) . . ?
N9 N8 C7 109.2(3) . . ?
N8 N9 N10 107.2(3) . . ?
C11 N10 N9 110.8(3) . . ?
C11 N10 C12 128.8(3) . . ?
N9 N10 C12 120.3(3) . . ?
N10 C11 C7 104.9(3) . . ?
N10 C11 H11A 127.5 . . ?
C7 C11 H11A 127.5 . . ?
N10 C12 C13 112.6(3) . . ?
N10 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N10 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
O14 C13 C15 111.5(3) . . ?
O14 C13 C12 106.8(3) . . ?
C15 C13 C12 111.9(2) . . ?
O14 C13 H13A 108.8 . . ?
C15 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C13 O14 H14A 109.5 . . ?
O16 C15 C13 105.7(2) . . ?
O16 C15 H15A 110.6 . . ?
C13 C15 H15A 110.6 . . ?
O16 C15 H15B 110.6 . . ?
C13 C15 H15B 110.6 . . ?
H15A C15 H15B 108.7 . . ?
C17 O16 C15 116.5(3) . . ?
O18 C17 O16 122.7(3) . . ?
O18 C17 C19 125.0(3) . . ?
O16 C17 C19 112.4(3) . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
C6 C1 C2 C3 0.3(6) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.5(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C2 C1 C6 C5 0.6(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
C1 C6 C7 N8 1.4(5) . . . . ?
C5 C6 C7 N8 -179.3(3) . . . . ?
C1 C6 C7 C11 -178.6(3) . . . . ?
C5 C6 C7 C11 0.8(5) . . . . ?
C11 C7 N8 N9 0.7(4) . . . . ?
C6 C7 N8 N9 -179.3(3) . . . . ?
C7 N8 N9 N10 -0.7(4) . . . . ?
N8 N9 N10 C11 0.5(4) . . . . ?
N8 N9 N10 C12 -177.1(3) . . . . ?
N9 N10 C11 C7 -0.1(3) . . . . ?
C12 N10 C11 C7 177.2(3) . . . . ?
N8 C7 C11 N10 -0.3(3) . . . . ?
C6 C7 C11 N10 179.6(3) . . . . ?
C11 N10 C12 C13 -87.6(4) . . . . ?
N9 N10 C12 C13 89.5(3) . . . . ?
N10 C12 C13 O14 55.3(3) . . . . ?
N10 C12 C13 C15 -67.0(4) . . . . ?
O14 C13 C15 O16 61.1(3) . . . . ?
C12 C13 C15 O16 -179.3(3) . . . . ?
C13 C15 O16 C17 -168.0(3) . . . . ?
C15 O16 C17 O18 -3.8(5) . . . . ?
C15 O16 C17 C19 176.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C11 H11A O18 0.95 2.42 3.168(4) 136.0 2_465 yes
C12 H12B O18 0.99 2.59 3.406(4) 139.8 2_465 yes
O14 H14A N9 0.84 2.04 2.826(4) 155.7 2_565 yes
C15 H15B N9 0.99 2.67 3.238(4) 116.6 . yes

_refine_diff_density_max         0.444
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.088

####################################################################### 
# 
# 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_ft45blua
_database_code_depnum_ccdc_archive 'CCDC 2191337'
loop_
_audit_author_name
_audit_author_address
'Anna Kozakiewicz-Piekarz'
;Faculty of Chemistry, Nicolaus Copernicus University in Torun
Poland
;
_audit_update_record             
;
2022-07-19 deposited with the CCDC.	2022-09-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'C16 H17 Cl Cu N3 O3, 0.5(C2 H4 O3), Cl, 0.5(H2 O)'
_chemical_formula_sum            'C17 H20 Cl2 Cu N3 O5'
_chemical_formula_weight         480.80

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/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                   10.154(2)
_cell_length_b                   15.904(3)
_cell_length_c                   23.353(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.03(2)
_cell_angle_gamma                90
_cell_volume                     3734.3(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9552
_cell_measurement_theta_min      3.2
_cell_measurement_theta_max      25

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.710
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    1.492
_shelx_estimated_absorpt_T_min   0.663
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_T_min  0.724
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Analytical numeric absorption correction using a multifaceted crystal
	model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_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_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Ruby
_diffrn_detector_area_resol_mean 10.3456
_diffrn_reflns_number            22639
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.266
_diffrn_reflns_theta_max         28.492
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8760
_reflns_number_gt                7105
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0372P)²+2.5608P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8760
_refine_ls_number_parameters     512
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0469
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0877
_refine_ls_wR_factor_gt          0.0808
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.10239(2) 0.91907(2) 0.54659(2) 0.01120(7) Uani 1 1 d . . . . .
Cl1 Cl -0.11943(5) 0.90782(3) 0.53647(2) 0.01511(11) Uani 1 1 d . . . . .
N1 N 0.30220(17) 0.93969(10) 0.55292(7) 0.0112(3) Uani 1 1 d . . . . .
C1 C 0.3874(2) 0.88029(12) 0.59295(9) 0.0129(4) Uani 1 1 d . . . . .
C2 C 0.3081(2) 0.83288(13) 0.63287(10) 0.0165(4) Uani 1 1 d . . . . .
H2A H 0.3596 0.7836 0.6494 0.020 Uiso 1 1 calc R U . . .
H2B H 0.2910 0.8699 0.6651 0.020 Uiso 1 1 calc R U . . .
O3 O 0.18450(15) 0.80546(9) 0.60153(7) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.1392 0.7922 0.6276 0.043(9) Uiso 1 1 d R . . . .
N1A N 0.12196(17) 0.99465(11) 0.61562(8) 0.0137(4) Uani 1 1 d . . . . .
C2A C 0.2412(2) 1.03341(12) 0.62620(9) 0.0138(4) Uani 1 1 d . . . . .
C3A C 0.2787(2) 1.07930(13) 0.67609(10) 0.0169(5) Uani 1 1 d . . . . .
H3A H 0.3638 1.1051 0.6831 0.020 Uiso 1 1 calc R U . . .
C4A C 0.1899(2) 1.08685(14) 0.71558(10) 0.0198(5) Uani 1 1 d . . . . .
H4A H 0.2127 1.1188 0.7499 0.024 Uiso 1 1 calc R U . . .
C5A C 0.0672(2) 1.04731(15) 0.70467(10) 0.0205(5) Uani 1 1 d . . . . .
H5A H 0.0051 1.0517 0.7314 0.025 Uiso 1 1 calc R U . . .
C6A C 0.0366(2) 1.00144(13) 0.65434(10) 0.0169(4) Uani 1 1 d . . . . .
H6A H -0.0471 0.9740 0.6470 0.020 Uiso 1 1 calc R U . . .
C7A C 0.3316(2) 1.02299(12) 0.58020(9) 0.0127(4) Uani 1 1 d . . . . .
H7A H 0.3143 1.0686 0.5506 0.015 Uiso 1 1 calc R U . . .
O8A O 0.46644(14) 1.02152(9) 0.60331(6) 0.0151(3) Uani 1 1 d . . . . .
C9A C 0.4930(2) 0.93859(13) 0.62699(10) 0.0160(4) Uani 1 1 d . . . . .
H9A1 H 0.4848 0.9379 0.6687 0.019 Uiso 1 1 calc R U . . .
H9A2 H 0.5838 0.9202 0.6220 0.019 Uiso 1 1 calc R U . . .
N1B N 0.12616(17) 0.86758(10) 0.47140(8) 0.0125(4) Uani 1 1 d . . . . .
C2B C 0.2445(2) 0.88365(12) 0.45386(9) 0.0125(4) Uani 1 1 d . . . . .
C3B C 0.2738(2) 0.85898(13) 0.40024(9) 0.0148(4) Uani 1 1 d . . . . .
H3B H 0.3568 0.8731 0.3884 0.018 Uiso 1 1 calc R U . . .
C4B C 0.1802(2) 0.81330(13) 0.36411(10) 0.0164(4) Uani 1 1 d . . . . .
H4B H 0.1981 0.7953 0.3272 0.020 Uiso 1 1 calc R U . . .
C5B C 0.0602(2) 0.79437(13) 0.38279(9) 0.0163(4) Uani 1 1 d . . . . .
H5B H -0.0046 0.7618 0.3592 0.020 Uiso 1 1 calc R U . . .
C6B C 0.0353(2) 0.82338(13) 0.43612(9) 0.0148(4) Uani 1 1 d . . . . .
H6B H -0.0483 0.8117 0.4482 0.018 Uiso 1 1 calc R U . . .
C7B C 0.3481(2) 0.93019(12) 0.49527(9) 0.0123(4) Uani 1 1 d . . . . .
H7B H 0.3659 0.9867 0.4792 0.015 Uiso 1 1 calc R U . . .
O8B O 0.46731(14) 0.88255(9) 0.50473(6) 0.0153(3) Uani 1 1 d . . . . .
C9B C 0.4463(2) 0.82467(13) 0.54989(10) 0.0168(4) Uani 1 1 d . . . . .
H9B1 H 0.5311 0.7991 0.5677 0.020 Uiso 1 1 calc R U . . .
H9B2 H 0.3836 0.7795 0.5350 0.020 Uiso 1 1 calc R U . . .
Cu2 Cu 0.60238(2) 0.57605(2) 0.54540(2) 0.01003(7) Uani 1 1 d . . . . .
Cl2 Cl 0.38080(5) 0.58966(3) 0.53284(2) 0.01448(11) Uani 1 1 d . . . . .
N2 N 0.80331(16) 0.56145(10) 0.55175(7) 0.0095(3) Uani 1 1 d . . . . .
C3 C 0.8861(2) 0.62918(12) 0.58647(9) 0.0124(4) Uani 1 1 d . . . . .
C4 C 0.8003(2) 0.70228(12) 0.60180(10) 0.0145(4) Uani 1 1 d . . . . .
H41 H 0.8488 0.7352 0.6340 0.017 Uiso 1 1 calc R U . . .
H42 H 0.7790 0.7399 0.5680 0.017 Uiso 1 1 calc R U . . .
O4 O 0.68131(15) 0.66888(10) 0.61831(7) 0.0199(3) Uani 1 1 d . . . . .
H4 H 0.6573 0.6953 0.6463 0.030(8) Uiso 1 1 d R . . . .
N1C N 0.63346(17) 0.64261(10) 0.47583(7) 0.0115(3) Uani 1 1 d . . . . .
C2C C 0.7504(2) 0.62591(12) 0.45700(9) 0.0112(4) Uani 1 1 d . . . . .
C3C C 0.7848(2) 0.66025(13) 0.40679(9) 0.0140(4) Uani 1 1 d . . . . .
H3C H 0.8661 0.6454 0.3936 0.017 Uiso 1 1 calc R U . . .
C4C C 0.6983(2) 0.71671(13) 0.37617(9) 0.0165(4) Uani 1 1 d . . . . .
H4C H 0.7196 0.7415 0.3416 0.020 Uiso 1 1 calc R U . . .
C5C C 0.5810(2) 0.73670(13) 0.39630(9) 0.0163(4) Uani 1 1 d . . . . .
H5C H 0.5222 0.7771 0.3767 0.020 Uiso 1 1 calc R U . . .
C6C C 0.5498(2) 0.69707(12) 0.44556(9) 0.0146(4) Uani 1 1 d . . . . .
H6C H 0.4668 0.7088 0.4583 0.017 Uiso 1 1 calc R U . . .
C7C C 0.8437(2) 0.56608(12) 0.49342(9) 0.0111(4) Uani 1 1 d . . . . .
H7C H 0.8388 0.5090 0.4753 0.013 Uiso 1 1 calc R U . . .
O8C O 0.97573(14) 0.59551(9) 0.50042(6) 0.0130(3) Uani 1 1 d . . . . .
C9C C 0.9847(2) 0.65708(13) 0.54575(9) 0.0151(4) Uani 1 1 d . . . . .
H9C1 H 0.9607 0.7135 0.5296 0.018 Uiso 1 1 calc R U . . .
H9C2 H 1.0763 0.6594 0.5668 0.018 Uiso 1 1 calc R U . . .
N1D N 0.61719(17) 0.49036(10) 0.60794(7) 0.0118(4) Uani 1 1 d . . . . .
C2D C 0.7393(2) 0.45731(12) 0.62121(9) 0.0128(4) Uani 1 1 d . . . . .
C3D C 0.7706(2) 0.40282(13) 0.66728(10) 0.0156(4) Uani 1 1 d . . . . .
H3D H 0.8575 0.3798 0.6757 0.019 Uiso 1 1 calc R U . . .
C4D C 0.6733(2) 0.38238(13) 0.70077(10) 0.0177(5) Uani 1 1 d . . . . .
H4D H 0.6923 0.3447 0.7324 0.021 Uiso 1 1 calc R U . . .
C5D C 0.5480(2) 0.41735(13) 0.68766(10) 0.0168(5) Uani 1 1 d . . . . .
H5D H 0.4801 0.4047 0.7105 0.020 Uiso 1 1 calc R U . . .
C6D C 0.5231(2) 0.47091(13) 0.64090(9) 0.0144(4) Uani 1 1 d . . . . .
H6D H 0.4369 0.4947 0.6317 0.017 Uiso 1 1 calc R U . . .
C7D C 0.8428(2) 0.48121(12) 0.58296(9) 0.0121(4) Uani 1 1 d . . . . .
H7D H 0.8516 0.4353 0.5545 0.015 Uiso 1 1 calc R U . . .
O8D O 0.96664(14) 0.49662(9) 0.61650(6) 0.0148(3) Uani 1 1 d . . . . .
C9D C 0.9529(2) 0.57991(12) 0.63861(10) 0.0154(4) Uani 1 1 d . . . . .
H9D1 H 1.0408 0.6042 0.6534 0.019 Uiso 1 1 calc R U . . .
H9D2 H 0.8969 0.5796 0.6701 0.019 Uiso 1 1 calc R U . . .
Cl3 Cl 0.60758(5) 0.77047(3) 0.71827(2) 0.01880(12) Uani 1 1 d . . . . .
Cl4 Cl 0.07451(5) 0.76258(4) 0.71114(2) 0.02094(12) Uani 1 1 d . . . . .
O1E O 0.23300(18) 0.49921(10) 0.70090(7) 0.0241(4) Uani 1 1 d . . . . .
H1E H 0.1651 0.4729 0.7076 0.110(18) Uiso 1 1 d R . . . .
O2E O 0.26894(19) 0.52432(11) 0.79608(8) 0.0297(4) Uani 1 1 d . . . . .
C1E C 0.2823(2) 0.54296(14) 0.74750(10) 0.0193(5) Uani 1 1 d . . . . .
C2E C 0.3562(2) 0.61915(15) 0.72988(10) 0.0241(5) Uani 1 1 d . . . . .
H2E1 H 0.4276 0.6009 0.7078 0.029 Uiso 1 1 calc R U . . .
H2E2 H 0.2942 0.6556 0.7045 0.029 Uiso 1 1 calc R U . . .
O3E O 0.41218(17) 0.66496(10) 0.77873(7) 0.0237(4) Uani 1 1 d . . . . .
H3E H 0.4640 0.7016 0.7688 0.041(9) Uiso 1 1 calc R . . . .
O1W O 0.87069(17) 0.85208(10) 0.77682(7) 0.0243(4) Uani 1 1 d . . . . .
H1W H 0.8013 0.8284 0.7606 0.049(10) Uiso 1 1 d R . . . .
H2W H 0.9402 0.8456 0.7616 0.066(12) Uiso 1 1 d R . . . .


_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 1.9824(18) . ?
Cu1 N1A 1.9985(18) . ?
Cu1 N1 2.0401(18) . ?
Cu1 Cl1 2.2388(7) . ?
Cu1 O3 2.3037(15) . ?
N1 C7A 1.482(2) . ?
N1 C7B 1.493(3) . ?
N1 C1 1.513(3) . ?
C1 C2 1.515(3) . ?
C1 C9B 1.523(3) . ?
C1 C9A 1.550(3) . ?
C2 O3 1.429(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
O3 H3 0.8400 . ?
N1A C6A 1.342(3) . ?
N1A C2A 1.350(3) . ?
C2A C3A 1.382(3) . ?
C2A C7A 1.517(3) . ?
C3A C4A 1.382(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.388(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.381(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A O8A 1.400(2) . ?
C7A H7A 1.0000 . ?
O8A C9A 1.441(2) . ?
C9A H9A1 0.9900 . ?
C9A H9A2 0.9900 . ?
N1B C6B 1.346(3) . ?
N1B C2B 1.347(3) . ?
C2B C3B 1.383(3) . ?
C2B C7B 1.518(3) . ?
C3B C4B 1.385(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.384(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.384(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B O8B 1.419(2) . ?
C7B H7B 1.0000 . ?
O8B C9B 1.438(3) . ?
C9B H9B1 0.9900 . ?
C9B H9B2 0.9900 . ?
Cu2 N1D 1.9878(17) . ?
Cu2 N1C 2.0006(18) . ?
Cu2 N2 2.0381(17) . ?
Cu2 Cl2 2.2384(7) . ?
Cu2 O4 2.3108(16) . ?
N2 C7C 1.478(3) . ?
N2 C7D 1.496(2) . ?
N2 C3 1.528(3) . ?
C3 C4 1.525(3) . ?
C3 C9D 1.525(3) . ?
C3 C9C 1.539(3) . ?
C4 O4 1.422(3) . ?
C4 H41 0.9900 . ?
C4 H42 0.9900 . ?
O4 H4 0.8399 . ?
N1C C6C 1.343(3) . ?
N1C C2C 1.350(3) . ?
C2C C3C 1.382(3) . ?
C2C C7C 1.517(3) . ?
C3C C4C 1.383(3) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.378(3) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.387(3) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
C7C O8C 1.408(2) . ?
C7C H7C 1.0000 . ?
O8C C9C 1.436(2) . ?
C9C H9C1 0.9900 . ?
C9C H9C2 0.9900 . ?
N1D C2D 1.343(3) . ?
N1D C6D 1.344(3) . ?
C2D C3D 1.383(3) . ?
C2D C7D 1.519(3) . ?
C3D C4D 1.382(3) . ?
C3D H3D 0.9500 . ?
C4D C5D 1.383(3) . ?
C4D H4D 0.9500 . ?
C5D C6D 1.380(3) . ?
C5D H5D 0.9500 . ?
C6D H6D 0.9500 . ?
C7D O8D 1.407(2) . ?
C7D H7D 1.0000 . ?
O8D C9D 1.436(2) . ?
C9D H9D1 0.9900 . ?
C9D H9D2 0.9900 . ?
O1E C1E 1.329(3) . ?
O1E H1E 0.8400 . ?
O2E C1E 1.199(3) . ?
C1E C2E 1.512(3) . ?
C2E O3E 1.405(3) . ?
C2E H2E1 0.9900 . ?
C2E H2E2 0.9900 . ?
O3E H3E 0.8400 . ?
O1W H1W 0.8403 . ?
O1W H2W 0.8402 . ?

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 162.22(7) . . ?
N1B Cu1 N1 83.56(7) . . ?
N1A Cu1 N1 81.89(7) . . ?
N1B Cu1 Cl1 96.82(6) . . ?
N1A Cu1 Cl1 96.80(6) . . ?
N1 Cu1 Cl1 174.99(5) . . ?
N1B Cu1 O3 95.16(6) . . ?
N1A Cu1 O3 92.00(6) . . ?
N1 Cu1 O3 78.86(6) . . ?
Cl1 Cu1 O3 106.06(4) . . ?
C7A N1 C7B 114.13(16) . . ?
C7A N1 C1 103.26(15) . . ?
C7B N1 C1 105.68(15) . . ?
C7A N1 Cu1 108.25(12) . . ?
C7B N1 Cu1 110.55(12) . . ?
C1 N1 Cu1 114.93(12) . . ?
N1 C1 C2 112.54(17) . . ?
N1 C1 C9B 101.42(16) . . ?
C2 C1 C9B 114.12(17) . . ?
N1 C1 C9A 103.78(15) . . ?
C2 C1 C9A 111.79(18) . . ?
C9B C1 C9A 112.28(18) . . ?
O3 C2 C1 109.94(17) . . ?
O3 C2 H2A 109.7 . . ?
C1 C2 H2A 109.7 . . ?
O3 C2 H2B 109.7 . . ?
C1 C2 H2B 109.7 . . ?
H2A C2 H2B 108.2 . . ?
C2 O3 Cu1 105.63(11) . . ?
C2 O3 H3 103.6 . . ?
Cu1 O3 H3 114.1 . . ?
C6A N1A C2A 119.15(18) . . ?
C6A N1A Cu1 126.26(15) . . ?
C2A N1A Cu1 114.07(14) . . ?
N1A C2A C3A 122.0(2) . . ?
N1A C2A C7A 115.87(18) . . ?
C3A C2A C7A 122.11(19) . . ?
C4A C3A C2A 118.6(2) . . ?
C4A C3A H3A 120.7 . . ?
C2A C3A H3A 120.7 . . ?
C3A C4A C5A 119.4(2) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C6A C5A C4A 119.0(2) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
N1A C6A C5A 121.8(2) . . ?
N1A C6A H6A 119.1 . . ?
C5A C6A H6A 119.1 . . ?
O8A C7A N1 106.13(16) . . ?
O8A C7A C2A 112.64(17) . . ?
N1 C7A C2A 107.26(16) . . ?
O8A C7A H7A 110.2 . . ?
N1 C7A H7A 110.2 . . ?
C2A C7A H7A 110.2 . . ?
C7A O8A C9A 106.47(15) . . ?
O8A C9A C1 105.78(16) . . ?
O8A C9A H9A1 110.6 . . ?
C1 C9A H9A1 110.6 . . ?
O8A C9A H9A2 110.6 . . ?
C1 C9A H9A2 110.6 . . ?
H9A1 C9A H9A2 108.7 . . ?
C6B N1B C2B 118.49(19) . . ?
C6B N1B Cu1 126.88(15) . . ?
C2B N1B Cu1 114.53(14) . . ?
N1B C2B C3B 122.33(19) . . ?
N1B C2B C7B 117.82(18) . . ?
C3B C2B C7B 119.85(19) . . ?
C2B C3B C4B 119.0(2) . . ?
C2B C3B H3B 120.5 . . ?
C4B C3B H3B 120.5 . . ?
C5B C4B C3B 118.8(2) . . ?
C5B C4B H4B 120.6 . . ?
C3B C4B H4B 120.6 . . ?
C6B C5B C4B 119.4(2) . . ?
C6B C5B H5B 120.3 . . ?
C4B C5B H5B 120.3 . . ?
N1B C6B C5B 122.0(2) . . ?
N1B C6B H6B 119.0 . . ?
C5B C6B H6B 119.0 . . ?
O8B C7B N1 106.31(16) . . ?
O8B C7B C2B 109.80(16) . . ?
N1 C7B C2B 110.38(17) . . ?
O8B C7B H7B 110.1 . . ?
N1 C7B H7B 110.1 . . ?
C2B C7B H7B 110.1 . . ?
C7B O8B C9B 104.18(15) . . ?
O8B C9B C1 102.99(16) . . ?
O8B C9B H9B1 111.2 . . ?
C1 C9B H9B1 111.2 . . ?
O8B C9B H9B2 111.2 . . ?
C1 C9B H9B2 111.2 . . ?
H9B1 C9B H9B2 109.1 . . ?
N1D Cu2 N1C 162.75(7) . . ?
N1D Cu2 N2 84.04(7) . . ?
N1C Cu2 N2 81.34(7) . . ?
N1D Cu2 Cl2 97.70(5) . . ?
N1C Cu2 Cl2 96.44(5) . . ?
N2 Cu2 Cl2 176.54(5) . . ?
N1D Cu2 O4 85.05(7) . . ?
N1C Cu2 O4 100.51(6) . . ?
N2 Cu2 O4 77.21(6) . . ?
Cl2 Cu2 O4 105.88(4) . . ?
C7C N2 C7D 113.67(15) . . ?
C7C N2 C3 104.54(15) . . ?
C7D N2 C3 104.63(15) . . ?
C7C N2 Cu2 109.32(12) . . ?
C7D N2 Cu2 109.28(12) . . ?
C3 N2 Cu2 115.42(12) . . ?
C4 C3 C9D 114.15(18) . . ?
C4 C3 N2 111.85(16) . . ?
C9D C3 N2 102.23(15) . . ?
C4 C3 C9C 111.55(17) . . ?
C9D C3 C9C 112.72(17) . . ?
N2 C3 C9C 103.45(16) . . ?
O4 C4 C3 108.28(16) . . ?
O4 C4 H41 110.0 . . ?
C3 C4 H41 110.0 . . ?
O4 C4 H42 110.0 . . ?
C3 C4 H42 110.0 . . ?
H41 C4 H42 108.4 . . ?
C4 O4 Cu2 105.03(12) . . ?
C4 O4 H4 111.9 . . ?
Cu2 O4 H4 141.6 . . ?
C6C N1C C2C 118.45(18) . . ?
C6C N1C Cu2 127.48(15) . . ?
C2C N1C Cu2 113.98(13) . . ?
N1C C2C C3C 122.48(19) . . ?
N1C C2C C7C 116.72(18) . . ?
C3C C2C C7C 120.80(18) . . ?
C2C C3C C4C 118.5(2) . . ?
C2C C3C H3C 120.7 . . ?
C4C C3C H3C 120.7 . . ?
C5C C4C C3C 119.4(2) . . ?
C5C C4C H4C 120.3 . . ?
C3C C4C H4C 120.3 . . ?
C4C C5C C6C 119.1(2) . . ?
C4C C5C H5C 120.4 . . ?
C6C C5C H5C 120.4 . . ?
N1C C6C C5C 121.9(2) . . ?
N1C C6C H6C 119.1 . . ?
C5C C6C H6C 119.1 . . ?
O8C C7C N2 106.96(16) . . ?
O8C C7C C2C 111.49(16) . . ?
N2 C7C C2C 108.44(16) . . ?
O8C C7C H7C 110.0 . . ?
N2 C7C H7C 110.0 . . ?
C2C C7C H7C 110.0 . . ?
C7C O8C C9C 105.89(15) . . ?
O8C C9C C3 106.21(16) . . ?
O8C C9C H9C1 110.5 . . ?
C3 C9C H9C1 110.5 . . ?
O8C C9C H9C2 110.5 . . ?
C3 C9C H9C2 110.5 . . ?
H9C1 C9C H9C2 108.7 . . ?
C2D N1D C6D 119.03(18) . . ?
C2D N1D Cu2 114.25(14) . . ?
C6D N1D Cu2 126.27(14) . . ?
N1D C2D C3D 121.9(2) . . ?
N1D C2D C7D 117.30(18) . . ?
C3D C2D C7D 120.78(19) . . ?
C4D C3D C2D 118.9(2) . . ?
C4D C3D H3D 120.5 . . ?
C2D C3D H3D 120.5 . . ?
C3D C4D C5D 119.2(2) . . ?
C3D C4D H4D 120.4 . . ?
C5D C4D H4D 120.4 . . ?
C6D C5D C4D 119.0(2) . . ?
C6D C5D H5D 120.5 . . ?
C4D C5D H5D 120.5 . . ?
N1D C6D C5D 121.9(2) . . ?
N1D C6D H6D 119.0 . . ?
C5D C6D H6D 119.0 . . ?
O8D C7D N2 106.30(15) . . ?
O8D C7D C2D 110.74(17) . . ?
N2 C7D C2D 109.84(16) . . ?
O8D C7D H7D 110.0 . . ?
N2 C7D H7D 110.0 . . ?
C2D C7D H7D 110.0 . . ?
C7D O8D C9D 103.70(15) . . ?
O8D C9D C3 103.98(16) . . ?
O8D C9D H9D1 111.0 . . ?
C3 C9D H9D1 111.0 . . ?
O8D C9D H9D2 111.0 . . ?
C3 C9D H9D2 111.0 . . ?
H9D1 C9D H9D2 109.0 . . ?
C1E O1E H1E 109.5 . . ?
O2E C1E O1E 124.5(2) . . ?
O2E C1E C2E 125.6(2) . . ?
O1E C1E C2E 109.9(2) . . ?
O3E C2E C1E 110.7(2) . . ?
O3E C2E H2E1 109.5 . . ?
C1E C2E H2E1 109.5 . . ?
O3E C2E H2E2 109.5 . . ?
C1E C2E H2E2 109.5 . . ?
H2E1 C2E H2E2 108.1 . . ?
C2E O3E H3E 109.5 . . ?
H1W O1W H2W 117.1 . . ?

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
C7A N1 C1 C2 101.87(19) . . . . ?
C7B N1 C1 C2 -137.98(17) . . . . ?
Cu1 N1 C1 C2 -15.8(2) . . . . ?
C7A N1 C1 C9B -135.78(17) . . . . ?
C7B N1 C1 C9B -15.62(19) . . . . ?
Cu1 N1 C1 C9B 106.56(15) . . . . ?
C7A N1 C1 C9A -19.2(2) . . . . ?
C7B N1 C1 C9A 100.99(18) . . . . ?
Cu1 N1 C1 C9A -136.84(14) . . . . ?
N1 C1 C2 O3 42.3(2) . . . . ?
C9B C1 C2 O3 -72.6(2) . . . . ?
C9A C1 C2 O3 158.66(17) . . . . ?
C1 C2 O3 Cu1 -44.79(19) . . . . ?
C6A N1A C2A C3A 0.7(3) . . . . ?
Cu1 N1A C2A C3A -171.53(16) . . . . ?
C6A N1A C2A C7A -179.72(18) . . . . ?
Cu1 N1A C2A C7A 8.1(2) . . . . ?
N1A C2A C3A C4A -1.3(3) . . . . ?
C7A C2A C3A C4A 179.09(19) . . . . ?
C2A C3A C4A C5A 1.1(3) . . . . ?
C3A C4A C5A C6A -0.2(3) . . . . ?
C2A N1A C6A C5A 0.3(3) . . . . ?
Cu1 N1A C6A C5A 171.42(16) . . . . ?
C4A C5A C6A N1A -0.5(3) . . . . ?
C7B N1 C7A O8A -78.2(2) . . . . ?
C1 N1 C7A O8A 36.0(2) . . . . ?
Cu1 N1 C7A O8A 158.26(12) . . . . ?
C7B N1 C7A C2A 161.18(16) . . . . ?
C1 N1 C7A C2A -84.63(18) . . . . ?
Cu1 N1 C7A C2A 37.63(18) . . . . ?
N1A C2A C7A O8A -147.26(17) . . . . ?
C3A C2A C7A O8A 32.3(3) . . . . ?
N1A C2A C7A N1 -30.8(2) . . . . ?
C3A C2A C7A N1 148.76(19) . . . . ?
N1 C7A O8A C9A -39.0(2) . . . . ?
C2A C7A O8A C9A 78.1(2) . . . . ?
C7A O8A C9A C1 25.4(2) . . . . ?
N1 C1 C9A O8A -2.8(2) . . . . ?
C2 C1 C9A O8A -124.30(18) . . . . ?
C9B C1 C9A O8A 105.95(19) . . . . ?
C6B N1B C2B C3B 2.4(3) . . . . ?
Cu1 N1B C2B C3B -174.25(15) . . . . ?
C6B N1B C2B C7B -177.32(17) . . . . ?
Cu1 N1B C2B C7B 6.1(2) . . . . ?
N1B C2B C3B C4B -2.6(3) . . . . ?
C7B C2B C3B C4B 177.13(18) . . . . ?
C2B C3B C4B C5B 0.4(3) . . . . ?
C3B C4B C5B C6B 1.8(3) . . . . ?
C2B N1B C6B C5B -0.1(3) . . . . ?
Cu1 N1B C6B C5B 176.11(15) . . . . ?
C4B C5B C6B N1B -2.0(3) . . . . ?
C7A N1 C7B O8B 101.83(18) . . . . ?
C1 N1 C7B O8B -10.92(19) . . . . ?
Cu1 N1 C7B O8B -135.87(13) . . . . ?
C7A N1 C7B C2B -139.14(17) . . . . ?
C1 N1 C7B C2B 108.11(17) . . . . ?
Cu1 N1 C7B C2B -16.84(18) . . . . ?
N1B C2B C7B O8B 124.49(19) . . . . ?
C3B C2B C7B O8B -55.2(2) . . . . ?
N1B C2B C7B N1 7.6(2) . . . . ?
C3B C2B C7B N1 -172.10(17) . . . . ?
N1 C7B O8B C9B 34.97(19) . . . . ?
C2B C7B O8B C9B -84.44(19) . . . . ?
C7B O8B C9B C1 -45.05(19) . . . . ?
N1 C1 C9B O8B 36.62(19) . . . . ?
C2 C1 C9B O8B 157.88(17) . . . . ?
C9A C1 C9B O8B -73.6(2) . . . . ?
C7C N2 C3 C4 111.27(18) . . . . ?
C7D N2 C3 C4 -128.98(18) . . . . ?
Cu2 N2 C3 C4 -8.9(2) . . . . ?
C7C N2 C3 C9D -126.18(17) . . . . ?
C7D N2 C3 C9D -6.4(2) . . . . ?
Cu2 N2 C3 C9D 113.70(15) . . . . ?
C7C N2 C3 C9C -8.91(19) . . . . ?
C7D N2 C3 C9C 110.84(17) . . . . ?
Cu2 N2 C3 C9C -129.03(14) . . . . ?
C9D C3 C4 O4 -74.1(2) . . . . ?
N2 C3 C4 O4 41.3(2) . . . . ?
C9C C3 C4 O4 156.65(17) . . . . ?
C3 C4 O4 Cu2 -49.89(18) . . . . ?
C6C N1C C2C C3C -2.4(3) . . . . ?
Cu2 N1C C2C C3C 174.45(16) . . . . ?
C6C N1C C2C C7C 178.25(17) . . . . ?
Cu2 N1C C2C C7C -4.9(2) . . . . ?
N1C C2C C3C C4C 2.9(3) . . . . ?
C7C C2C C3C C4C -177.82(18) . . . . ?
C2C C3C C4C C5C -0.3(3) . . . . ?
C3C C4C C5C C6C -2.6(3) . . . . ?
C2C N1C C6C C5C -0.6(3) . . . . ?
Cu2 N1C C6C C5C -177.07(15) . . . . ?
C4C C5C C6C N1C 3.2(3) . . . . ?
C7D N2 C7C O8C -85.00(18) . . . . ?
C3 N2 C7C O8C 28.48(18) . . . . ?
Cu2 N2 C7C O8C 152.61(12) . . . . ?
C7D N2 C7C C2C 154.65(16) . . . . ?
C3 N2 C7C C2C -91.87(17) . . . . ?
Cu2 N2 C7C C2C 32.25(17) . . . . ?
N1C C2C C7C O8C -136.14(18) . . . . ?
C3C C2C C7C O8C 44.5(3) . . . . ?
N1C C2C C7C N2 -18.6(2) . . . . ?
C3C C2C C7C N2 162.03(18) . . . . ?
N2 C7C O8C C9C -37.67(19) . . . . ?
C2C C7C O8C C9C 80.72(19) . . . . ?
C7C O8C C9C C3 31.0(2) . . . . ?
C4 C3 C9C O8C -133.18(17) . . . . ?
C9D C3 C9C O8C 96.86(19) . . . . ?
N2 C3 C9C O8C -12.8(2) . . . . ?
C6D N1D C2D C3D 1.0(3) . . . . ?
Cu2 N1D C2D C3D 173.76(16) . . . . ?
C6D N1D C2D C7D -179.77(18) . . . . ?
Cu2 N1D C2D C7D -7.0(2) . . . . ?
N1D C2D C3D C4D -0.5(3) . . . . ?
C7D C2D C3D C4D -179.65(19) . . . . ?
C2D C3D C4D C5D -0.5(3) . . . . ?
C3D C4D C5D C6D 0.9(3) . . . . ?
C2D N1D C6D C5D -0.6(3) . . . . ?
Cu2 N1D C6D C5D -172.41(15) . . . . ?
C4D C5D C6D N1D -0.3(3) . . . . ?
C7C N2 C7D O8D 93.28(19) . . . . ?
C3 N2 C7D O8D -20.2(2) . . . . ?
Cu2 N2 C7D O8D -144.30(13) . . . . ?
C7C N2 C7D C2D -146.87(17) . . . . ?
C3 N2 C7D C2D 99.69(18) . . . . ?
Cu2 N2 C7D C2D -24.46(19) . . . . ?
N1D C2D C7D O8D 138.54(18) . . . . ?
C3D C2D C7D O8D -42.2(3) . . . . ?
N1D C2D C7D N2 21.4(2) . . . . ?
C3D C2D C7D N2 -159.33(18) . . . . ?
N2 C7D O8D C9D 40.3(2) . . . . ?
C2D C7D O8D C9D -78.94(19) . . . . ?
C7D O8D C9D C3 -44.2(2) . . . . ?
C4 C3 C9D O8D 151.27(17) . . . . ?
N2 C3 C9D O8D 30.3(2) . . . . ?
C9C C3 C9D O8D -80.11(19) . . . . ?
O2E C1E C2E O3E 1.9(3) . . . . ?
O1E C1E C2E O3E -178.41(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 Cl4 0.84 2.19 3.0104(18) 163.9 .
C6A H6A Cl1 0.95 2.79 3.330(2) 117.1 .
C7A H7A Cl1 1.00 2.66 3.411(2) 132.1 3_576
C3B H3B O8A 0.95 2.44 3.262(3) 144.2 3_676
C6B H6B Cl1 0.95 2.74 3.285(2) 117.0 .
C4 H41 Cl4 0.99 2.74 3.634(2) 149.7 1_655
O4 H4 Cl3 0.84 2.18 3.0181(17) 175.6 .
C7C H7C Cl2 1.00 2.71 3.364(2) 123.2 3_666
C6D H6D Cl2 0.95 2.75 3.317(2) 118.9 .
C7D H7D O8C 1.00 2.36 3.111(3) 130.8 3_766
O1E H1E O1W 0.84 2.00 2.647(2) 133.5 2_646
O3E H3E Cl3 0.84 2.28 3.0868(19) 161.4 .
O1W H1W Cl3 0.84 2.27 3.1097(19) 176.9 .
O1W H2W Cl4 0.84 2.33 3.0902(19) 150.3 1_655

_refine_diff_density_max         0.570
_refine_diff_density_min         -0.568
_refine_diff_density_rms         0.079

_shelxl_version_number           2013-2

