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

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

data_tri_bluecx4a_a_pl
_database_code_depnum_ccdc_archive 'CCDC 2264849'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C26 H29 Cl Cu N3'
_chemical_formula_weight         482.51

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

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

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

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

_cell_length_a                   13.1798(15)
_cell_length_b                   14.1584(16)
_cell_length_c                   12.8105(15)
_cell_angle_alpha                90
_cell_angle_beta                 97.399(11)
_cell_angle_gamma                90
_cell_volume                     2370.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1086
_cell_measurement_theta_min      2.1186
_cell_measurement_theta_max      17.4299
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.233
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.052
_shelx_estimated_absorpt_T_min   0.792
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.8083
_exptl_absorpt_correction_T_max  0.9273
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            196946
_diffrn_reflns_av_unetI/netI     0.099
_diffrn_reflns_av_R_equivalents  0.169
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.535
_diffrn_reflns_theta_max         33.136
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8400
_reflns_number_gt                2889
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.1050P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8400
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2849
_refine_ls_R_factor_gt           0.0742
_refine_ls_wR_factor_ref         0.2342
_refine_ls_wR_factor_gt          0.1535
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_restrained_S_all      0.933
_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
Cu Cu 1.24797(5) 0.69903(4) 0.83928(5) 0.0347(2) Uani 1 1 d . . . . .
Cl Cl 1.17134(10) 0.55470(9) 0.84730(10) 0.0423(3) Uani 1 1 d . . . . .
N1 N 1.2010(3) 0.8220(3) 0.6486(3) 0.0283(9) Uani 1 1 d . . . . .
N2 N 1.1314(3) 0.8700(3) 0.7795(3) 0.0274(9) Uani 1 1 d . . . . .
N3 N 1.3667(3) 0.8206(3) 0.4590(3) 0.0310(9) Uani 1 1 d . . . . .
C1 C 1.1947(3) 0.8018(3) 0.7512(3) 0.0276(10) Uani 1 1 d . . . . .
C2 C 1.1428(4) 0.8988(3) 0.6145(4) 0.0344(12) Uani 1 1 d . . . . .
H2 H 1.135440 0.925451 0.545894 0.041 Uiso 1 1 calc R U . . .
C3 C 1.0979(4) 0.9295(3) 0.6972(4) 0.0335(11) Uani 1 1 d . . . . .
H3 H 1.052447 0.981429 0.698327 0.040 Uiso 1 1 calc R U . . .
C4 C 1.2560(4) 0.7655(3) 0.5809(4) 0.0321(11) Uani 1 1 d . . . . .
H4A H 1.211675 0.755278 0.513327 0.039 Uiso 1 1 calc R U . . .
H4B H 1.270443 0.702978 0.614017 0.039 Uiso 1 1 calc R U . . .
C5 C 1.3555(3) 0.8089(3) 0.5583(4) 0.0286(10) Uani 1 1 d . . . . .
C6 C 1.4312(4) 0.8310(4) 0.6421(4) 0.0407(13) Uani 1 1 d . . . . .
H6 H 1.417782 0.823219 0.712661 0.049 Uiso 1 1 calc R U . . .
C7 C 1.5245(4) 0.8638(4) 0.6219(5) 0.0428(14) Uani 1 1 d . . . . .
C8 C 1.5403(4) 0.8774(3) 0.5161(5) 0.0388(13) Uani 1 1 d . . . . .
C9 C 1.6328(4) 0.9133(4) 0.4855(6) 0.0566(17) Uani 1 1 d . . . . .
H9 H 1.687787 0.929927 0.537662 0.068 Uiso 1 1 calc R U . . .
C10 C 1.6430(5) 0.9239(4) 0.3820(6) 0.0581(17) Uani 1 1 d . . . . .
H10 H 1.706041 0.945697 0.362497 0.070 Uiso 1 1 calc R U . . .
C11 C 1.5623(5) 0.9032(4) 0.3039(5) 0.0616(18) Uani 1 1 d . . . . .
H11 H 1.570485 0.912137 0.231994 0.074 Uiso 1 1 calc R U . . .
C12 C 1.4716(4) 0.8704(4) 0.3300(5) 0.0494(15) Uani 1 1 d . . . . .
H12 H 1.416709 0.856938 0.276431 0.059 Uiso 1 1 calc R U . . .
C13 C 1.4592(4) 0.8562(3) 0.4374(4) 0.0359(12) Uani 1 1 d . . . . .
C14 C 1.6078(5) 0.8820(5) 0.7113(6) 0.071(2) Uani 1 1 d . . . . .
H14A H 1.631709 0.947356 0.707641 0.107 Uiso 1 1 calc R U . . .
H14B H 1.664960 0.838704 0.706153 0.107 Uiso 1 1 calc R U . . .
H14C H 1.581120 0.871933 0.778354 0.107 Uiso 1 1 calc R U . . .
C15 C 1.1071(3) 0.8807(3) 0.8859(3) 0.0269(10) Uani 1 1 d . . . . .
C16 C 1.0283(3) 0.8255(3) 0.9172(4) 0.0290(11) Uani 1 1 d . . . . .
C17 C 1.0100(4) 0.8367(4) 1.0207(4) 0.0351(12) Uani 1 1 d . . . . .
H17 H 0.957993 0.800083 1.046002 0.042 Uiso 1 1 calc R U . . .
C18 C 1.0654(4) 0.8997(3) 1.0881(4) 0.0348(12) Uani 1 1 d . . . . .
H18 H 1.049995 0.906567 1.158108 0.042 Uiso 1 1 calc R U . . .
C19 C 1.1427(4) 0.9526(3) 1.0544(4) 0.0321(11) Uani 1 1 d . . . . .
H19 H 1.179906 0.995729 1.101620 0.039 Uiso 1 1 calc R U . . .
C20 C 1.1671(3) 0.9439(3) 0.9522(4) 0.0294(10) Uani 1 1 d . . . . .
C21 C 1.2570(4) 0.9956(3) 0.9178(4) 0.0376(12) Uani 1 1 d . . . . .
H21 H 1.253163 0.987869 0.839760 0.045 Uiso 1 1 calc R U . . .
C22 C 1.2567(6) 1.1002(4) 0.9405(6) 0.078(2) Uani 1 1 d . . . . .
H22A H 1.318828 1.129008 0.920046 0.117 Uiso 1 1 calc R U . . .
H22B H 1.254653 1.110241 1.015892 0.117 Uiso 1 1 calc R U . . .
H22C H 1.196434 1.129312 0.900320 0.117 Uiso 1 1 calc R U . . .
C23 C 1.3556(4) 0.9504(5) 0.9667(6) 0.068(2) Uani 1 1 d . . . . .
H23A H 1.413587 0.981932 0.940664 0.102 Uiso 1 1 calc R U . . .
H23B H 1.355419 0.883373 0.947731 0.102 Uiso 1 1 calc R U . . .
H23C H 1.361670 0.956685 1.043428 0.102 Uiso 1 1 calc R U . . .
C24 C 0.9661(4) 0.7596(3) 0.8416(4) 0.0362(12) Uani 1 1 d . . . . .
H24 H 1.012626 0.731402 0.794231 0.043 Uiso 1 1 calc R U . . .
C25 C 0.9169(5) 0.6784(4) 0.8973(5) 0.0577(17) Uani 1 1 d . . . . .
H25A H 0.885476 0.633324 0.844725 0.087 Uiso 1 1 calc R U . . .
H25B H 0.864455 0.703874 0.937157 0.087 Uiso 1 1 calc R U . . .
H25C H 0.969610 0.646188 0.945514 0.087 Uiso 1 1 calc R U . . .
C26 C 0.8821(4) 0.8131(4) 0.7738(5) 0.0537(16) Uani 1 1 d . . . . .
H26A H 0.841984 0.768933 0.726102 0.081 Uiso 1 1 calc R U . . .
H26B H 0.912860 0.861061 0.732475 0.081 Uiso 1 1 calc R U . . .
H26C H 0.837346 0.843817 0.818942 0.081 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
Cu C1 1.918(5) . ?
Cu N3 2.064(4) 4_576 ?
Cu Cl 2.2877(14) . ?
N1 C1 1.358(5) . ?
N1 C2 1.370(6) . ?
N1 C4 1.442(6) . ?
N2 C1 1.356(6) . ?
N2 C3 1.377(6) . ?
N2 C15 1.447(6) . ?
N3 C5 1.310(6) . ?
N3 C13 1.380(6) . ?
C2 C3 1.349(7) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.510(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.403(7) . ?
C6 C7 1.370(7) . ?
C6 H6 0.9500 . ?
C7 C8 1.411(8) . ?
C7 C14 1.504(8) . ?
C8 C13 1.404(7) . ?
C8 C9 1.422(8) . ?
C9 C10 1.358(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.394(9) . ?
C10 H10 0.9500 . ?
C11 C12 1.364(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.420(7) . ?
C12 H12 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.400(6) . ?
C15 C20 1.406(6) . ?
C16 C17 1.387(7) . ?
C16 C24 1.508(7) . ?
C17 C18 1.382(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(7) . ?
C18 H18 0.9500 . ?
C19 C20 1.393(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.506(7) . ?
C21 C22 1.510(7) . ?
C21 C23 1.509(7) . ?
C21 H21 1.0000 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C26 1.518(7) . ?
C24 C25 1.540(8) . ?
C24 H24 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 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
C1 Cu N3 136.41(17) . 4_576 ?
C1 Cu Cl 125.03(14) . . ?
N3 Cu Cl 98.22(11) 4_576 . ?
C1 N1 C2 112.0(4) . . ?
C1 N1 C4 124.3(4) . . ?
C2 N1 C4 123.6(4) . . ?
C1 N2 C3 112.2(4) . . ?
C1 N2 C15 123.0(4) . . ?
C3 N2 C15 124.7(4) . . ?
C5 N3 C13 117.0(4) . . ?
C5 N3 Cu 122.3(3) . 4_575 ?
C13 N3 Cu 120.3(3) . 4_575 ?
N2 C1 N1 103.0(4) . . ?
N2 C1 Cu 125.0(3) . . ?
N1 C1 Cu 131.8(3) . . ?
C3 C2 N1 106.8(4) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 105.9(4) . . ?
C2 C3 H3 127.0 . . ?
N2 C3 H3 127.0 . . ?
N1 C4 C5 113.9(4) . . ?
N1 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
N1 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N3 C5 C6 123.8(4) . . ?
N3 C5 C4 116.5(4) . . ?
C6 C5 C4 119.6(4) . . ?
C7 C6 C5 119.9(5) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C6 C7 C8 118.4(5) . . ?
C6 C7 C14 120.0(6) . . ?
C8 C7 C14 121.6(5) . . ?
C13 C8 C7 117.9(5) . . ?
C13 C8 C9 118.6(5) . . ?
C7 C8 C9 123.5(5) . . ?
C10 C9 C8 120.3(6) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 121.0(6) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 120.5(6) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.9(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
N3 C13 C8 123.0(5) . . ?
N3 C13 C12 117.4(5) . . ?
C8 C13 C12 119.6(5) . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C20 124.3(4) . . ?
C16 C15 N2 118.3(4) . . ?
C20 C15 N2 117.4(4) . . ?
C17 C16 C15 115.8(4) . . ?
C17 C16 C24 122.6(4) . . ?
C15 C16 C24 121.6(4) . . ?
C18 C17 C16 121.9(5) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C19 C18 C17 120.5(5) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 121.0(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C15 116.4(4) . . ?
C19 C20 C21 121.2(4) . . ?
C15 C20 C21 122.3(4) . . ?
C20 C21 C22 113.5(5) . . ?
C20 C21 C23 109.9(4) . . ?
C22 C21 C23 111.0(5) . . ?
C20 C21 H21 107.4 . . ?
C22 C21 H21 107.4 . . ?
C23 C21 H21 107.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C16 C24 C26 110.8(4) . . ?
C16 C24 C25 113.0(4) . . ?
C26 C24 C25 108.6(5) . . ?
C16 C24 H24 108.1 . . ?
C26 C24 H24 108.1 . . ?
C25 C24 H24 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 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
C3 N2 C1 N1 1.1(5) . . . . ?
C15 N2 C1 N1 -175.9(4) . . . . ?
C3 N2 C1 Cu -174.3(3) . . . . ?
C15 N2 C1 Cu 8.7(6) . . . . ?
C2 N1 C1 N2 -0.8(5) . . . . ?
C4 N1 C1 N2 -176.4(4) . . . . ?
C2 N1 C1 Cu 174.1(4) . . . . ?
C4 N1 C1 Cu -1.5(7) . . . . ?
C1 N1 C2 C3 0.2(5) . . . . ?
C4 N1 C2 C3 175.9(4) . . . . ?
N1 C2 C3 N2 0.5(5) . . . . ?
C1 N2 C3 C2 -1.0(5) . . . . ?
C15 N2 C3 C2 176.0(4) . . . . ?
C1 N1 C4 C5 -105.7(5) . . . . ?
C2 N1 C4 C5 79.1(5) . . . . ?
C13 N3 C5 C6 0.5(7) . . . . ?
Cu N3 C5 C6 -173.1(4) 4_575 . . . ?
C13 N3 C5 C4 -177.1(4) . . . . ?
Cu N3 C5 C4 9.3(6) 4_575 . . . ?
N1 C4 C5 N3 -124.3(4) . . . . ?
N1 C4 C5 C6 58.0(6) . . . . ?
N3 C5 C6 C7 -2.4(8) . . . . ?
C4 C5 C6 C7 175.1(5) . . . . ?
C5 C6 C7 C8 2.1(8) . . . . ?
C5 C6 C7 C14 -176.4(5) . . . . ?
C6 C7 C8 C13 -0.2(7) . . . . ?
C14 C7 C8 C13 178.3(5) . . . . ?
C6 C7 C8 C9 178.4(5) . . . . ?
C14 C7 C8 C9 -3.1(8) . . . . ?
C13 C8 C9 C10 -2.0(8) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C8 C9 C10 C11 2.3(9) . . . . ?
C9 C10 C11 C12 -1.1(10) . . . . ?
C10 C11 C12 C13 -0.5(9) . . . . ?
C5 N3 C13 C8 1.6(7) . . . . ?
Cu N3 C13 C8 175.4(4) 4_575 . . . ?
C5 N3 C13 C12 -179.2(4) . . . . ?
Cu N3 C13 C12 -5.4(6) 4_575 . . . ?
C7 C8 C13 N3 -1.7(7) . . . . ?
C9 C8 C13 N3 179.6(5) . . . . ?
C7 C8 C13 C12 179.0(5) . . . . ?
C9 C8 C13 C12 0.4(7) . . . . ?
C11 C12 C13 N3 -178.4(5) . . . . ?
C11 C12 C13 C8 0.8(8) . . . . ?
C1 N2 C15 C16 -84.3(5) . . . . ?
C3 N2 C15 C16 99.1(5) . . . . ?
C1 N2 C15 C20 93.6(5) . . . . ?
C3 N2 C15 C20 -83.1(5) . . . . ?
C20 C15 C16 C17 0.7(7) . . . . ?
N2 C15 C16 C17 178.3(4) . . . . ?
C20 C15 C16 C24 179.4(4) . . . . ?
N2 C15 C16 C24 -2.9(6) . . . . ?
C15 C16 C17 C18 1.0(7) . . . . ?
C24 C16 C17 C18 -177.8(4) . . . . ?
C16 C17 C18 C19 -1.2(7) . . . . ?
C17 C18 C19 C20 -0.2(7) . . . . ?
C18 C19 C20 C15 1.7(7) . . . . ?
C18 C19 C20 C21 -174.9(4) . . . . ?
C16 C15 C20 C19 -2.0(7) . . . . ?
N2 C15 C20 C19 -179.7(4) . . . . ?
C16 C15 C20 C21 174.6(4) . . . . ?
N2 C15 C20 C21 -3.1(6) . . . . ?
C19 C20 C21 C22 -52.2(7) . . . . ?
C15 C20 C21 C22 131.4(6) . . . . ?
C19 C20 C21 C23 72.8(6) . . . . ?
C15 C20 C21 C23 -103.6(6) . . . . ?
C17 C16 C24 C26 97.0(6) . . . . ?
C15 C16 C24 C26 -81.7(6) . . . . ?
C17 C16 C24 C25 -25.1(7) . . . . ?
C15 C16 C24 C25 156.2(4) . . . . ?

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.612
_refine_diff_density_rms         0.098

####################################################################### 
# 
# 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_CuNHOCCl_100K
_database_code_depnum_ccdc_archive 'CCDC 2264867'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C24 H31 Cl Cu N3 O'
_chemical_formula_weight         476.51

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/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   10.5133(13)
_cell_length_b                   12.5355(15)
_cell_length_c                   17.866(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.654(4)
_cell_angle_gamma                90
_cell_volume                     2327.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1839
_cell_measurement_theta_min      2.0541
_cell_measurement_theta_max      29.6725
_cell_measurement_temperature    103.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.266
_exptl_crystal_size_mid          0.262
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    1.073
_shelx_estimated_absorpt_T_min   0.763
_shelx_estimated_absorpt_T_max   0.790
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.8080
_exptl_absorpt_correction_T_max  0.8737
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            82654
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5337
_reflns_number_gt                4757
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0432P)²+2.8561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5337
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0899
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
Cu Cu 0.75841(2) 0.31636(2) 0.76894(2) 0.01771(8) Uani 1 1 d . . . . .
Cl1 Cl 0.63997(6) 0.27737(4) 0.85718(3) 0.03094(13) Uani 1 1 d . . . . .
O1 O 0.21396(14) 0.59634(14) 0.62656(9) 0.0282(3) Uani 1 1 d . . . . .
N1 N 0.70848(15) 0.49819(12) 0.66459(9) 0.0155(3) Uani 1 1 d . . . . .
N2 N 0.75477(15) 0.35704(12) 0.60721(9) 0.0153(3) Uani 1 1 d . . . . .
N3 N 0.56621(16) 0.73873(13) 0.69839(9) 0.0176(3) Uani 1 1 d . . . . .
C1 C 0.73878(17) 0.39383(14) 0.67690(10) 0.0150(3) Uani 1 1 d . . . . .
C2 C 0.70647(19) 0.52661(15) 0.58940(11) 0.0192(4) Uani 1 1 d . . . . .
H2 H 0.688753 0.595256 0.567801 0.023 Uiso 1 1 calc R U . . .
C3 C 0.73470(19) 0.43736(15) 0.55306(11) 0.0193(4) Uani 1 1 d . . . . .
H3 H 0.739857 0.430675 0.500634 0.023 Uiso 1 1 calc R U . . .
C4 C 0.67625(18) 0.57008(14) 0.72360(10) 0.0165(4) Uani 1 1 d . . . . .
H4A H 0.747900 0.620982 0.737530 0.020 Uiso 1 1 calc R U . . .
H4B H 0.666490 0.527878 0.769233 0.020 Uiso 1 1 calc R U . . .
C5 C 0.55379(18) 0.63163(15) 0.69856(10) 0.0163(4) Uani 1 1 d . . . . .
C6 C 0.43575(19) 0.58054(16) 0.67738(11) 0.0208(4) Uani 1 1 d . . . . .
C7 C 0.32915(19) 0.64514(18) 0.65323(11) 0.0213(4) Uani 1 1 d . . . . .
C8 C 0.3395(2) 0.75607(17) 0.65233(11) 0.0222(4) Uani 1 1 d . . . . .
C9 C 0.4606(2) 0.79768(16) 0.67663(11) 0.0217(4) Uani 1 1 d . . . . .
H9 H 0.469508 0.873096 0.678003 0.026 Uiso 1 1 calc R U . . .
C10 C 0.4220(2) 0.46100(18) 0.67983(17) 0.0352(6) Uani 1 1 d . . . . .
H10A H 0.336551 0.442730 0.691516 0.053 Uiso 1 1 calc R U . . .
H10B H 0.488021 0.431665 0.719017 0.053 Uiso 1 1 calc R U . . .
H10C H 0.432644 0.430838 0.630534 0.053 Uiso 1 1 calc R U . . .
C11 C 0.2271(2) 0.82787(19) 0.62539(13) 0.0303(5) Uani 1 1 d . . . . .
H11A H 0.256709 0.902018 0.625401 0.045 Uiso 1 1 calc R U . . .
H11B H 0.162491 0.820942 0.659288 0.045 Uiso 1 1 calc R U . . .
H11C H 0.189095 0.807398 0.573929 0.045 Uiso 1 1 calc R U . . .
C12 C 0.1247(2) 0.5903(2) 0.67959(14) 0.0332(5) Uani 1 1 d . . . . .
H12A H 0.160956 0.545816 0.722648 0.050 Uiso 1 1 calc R U . . .
H12B H 0.043841 0.558937 0.654859 0.050 Uiso 1 1 calc R U . . .
H12C H 0.108335 0.662198 0.697537 0.050 Uiso 1 1 calc R U . . .
C13 C 0.78310(18) 0.24698(14) 0.59194(10) 0.0149(3) Uani 1 1 d . . . . .
C14 C 0.6825(2) 0.17285(16) 0.58260(11) 0.0206(4) Uani 1 1 d . . . . .
C15 C 0.7123(2) 0.06733(17) 0.56718(12) 0.0283(5) Uani 1 1 d . . . . .
H15 H 0.645612 0.015528 0.560469 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8359(3) 0.03683(17) 0.56151(12) 0.0298(5) Uani 1 1 d . . . . .
H16 H 0.853846 -0.035105 0.550020 0.036 Uiso 1 1 calc R U . . .
C17 C 0.9339(2) 0.11071(17) 0.57251(12) 0.0257(4) Uani 1 1 d . . . . .
H17 H 1.019294 0.088722 0.569046 0.031 Uiso 1 1 calc R U . . .
C18 C 0.91030(19) 0.21762(16) 0.58870(10) 0.0180(4) Uani 1 1 d . . . . .
C19 C 1.0197(2) 0.29685(18) 0.60383(12) 0.0252(4) Uani 1 1 d . . . . .
H19 H 0.994434 0.353166 0.638421 0.030 Uiso 1 1 calc R U . . .
C20 C 1.1433(2) 0.2441(3) 0.64298(14) 0.0419(7) Uani 1 1 d . . . . .
H20A H 1.124103 0.201156 0.685758 0.063 Uiso 1 1 calc R U . . .
H20B H 1.206333 0.299234 0.661422 0.063 Uiso 1 1 calc R U . . .
H20C H 1.178596 0.197997 0.606835 0.063 Uiso 1 1 calc R U . . .
C21 C 1.0464(2) 0.3514(2) 0.53107(14) 0.0317(5) Uani 1 1 d . . . . .
H21A H 1.072096 0.297736 0.496380 0.047 Uiso 1 1 calc R U . . .
H21B H 1.115734 0.403631 0.543355 0.047 Uiso 1 1 calc R U . . .
H21C H 0.968340 0.387779 0.506910 0.047 Uiso 1 1 calc R U . . .
C22 C 0.5452(2) 0.2040(2) 0.59032(13) 0.0303(5) Uani 1 1 d . . . . .
H22 H 0.547554 0.270560 0.621325 0.036 Uiso 1 1 calc R U . . .
C23 C 0.4659(3) 0.2246(2) 0.51437(15) 0.0410(6) Uani 1 1 d . . . . .
H23A H 0.506857 0.280481 0.487924 0.062 Uiso 1 1 calc R U . . .
H23B H 0.379489 0.247825 0.521461 0.062 Uiso 1 1 calc R U . . .
H23C H 0.459620 0.158975 0.484237 0.062 Uiso 1 1 calc R U . . .
C24 C 0.4801(3) 0.1140(4) 0.63126(19) 0.0648(11) Uani 1 1 d . . . . .
H24A H 0.400813 0.141373 0.646904 0.097 Uiso 1 1 calc R U . . .
H24B H 0.538955 0.090357 0.675980 0.097 Uiso 1 1 calc R U . . .
H24C H 0.459494 0.053692 0.596661 0.097 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
Cu C1 1.8941(18) . ?
Cu N3 2.0889(17) 2_646 ?
Cu Cl1 2.2057(6) . ?
O1 C7 1.376(2) . ?
O1 C12 1.432(3) . ?
N1 C1 1.357(2) . ?
N1 C2 1.387(2) . ?
N1 C4 1.465(2) . ?
N2 C1 1.362(2) . ?
N2 C3 1.390(2) . ?
N2 C13 1.446(2) . ?
N3 C9 1.342(3) . ?
N3 C5 1.349(2) . ?
C2 C3 1.349(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.510(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.397(3) . ?
C6 C7 1.397(3) . ?
C6 C10 1.507(3) . ?
C7 C8 1.395(3) . ?
C8 C9 1.383(3) . ?
C8 C11 1.506(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.397(3) . ?
C13 C14 1.399(3) . ?
C14 C15 1.396(3) . ?
C14 C22 1.521(3) . ?
C15 C16 1.373(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.401(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.513(3) . ?
C19 C20 1.531(3) . ?
C19 C21 1.532(3) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.505(3) . ?
C22 C24 1.558(4) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 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
C1 Cu N3 117.23(7) . 2_646 ?
C1 Cu Cl1 137.28(6) . . ?
N3 Cu Cl1 105.46(5) 2_646 . ?
C7 O1 C12 115.10(16) . . ?
C1 N1 C2 111.95(15) . . ?
C1 N1 C4 123.42(15) . . ?
C2 N1 C4 124.58(15) . . ?
C1 N2 C3 111.37(15) . . ?
C1 N2 C13 123.57(15) . . ?
C3 N2 C13 125.01(15) . . ?
C9 N3 C5 118.20(17) . . ?
C9 N3 Cu 118.79(13) . 2_656 ?
C5 N3 Cu 123.00(13) . 2_656 ?
N1 C1 N2 103.69(15) . . ?
N1 C1 Cu 128.86(14) . . ?
N2 C1 Cu 127.44(13) . . ?
C3 C2 N1 106.31(16) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 106.68(16) . . ?
C2 C3 H3 126.7 . . ?
N2 C3 H3 126.7 . . ?
N1 C4 C5 112.35(15) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.9 . . ?
N3 C5 C6 122.54(17) . . ?
N3 C5 C4 115.52(16) . . ?
C6 C5 C4 121.94(17) . . ?
C5 C6 C7 117.16(18) . . ?
C5 C6 C10 122.21(19) . . ?
C7 C6 C10 120.64(19) . . ?
O1 C7 C8 120.36(19) . . ?
O1 C7 C6 118.19(19) . . ?
C8 C7 C6 121.38(19) . . ?
C9 C8 C7 116.24(18) . . ?
C9 C8 C11 121.0(2) . . ?
C7 C8 C11 122.7(2) . . ?
N3 C9 C8 124.43(19) . . ?
N3 C9 H9 117.8 . . ?
C8 C9 H9 117.8 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.10(17) . . ?
C18 C13 N2 119.01(16) . . ?
C14 C13 N2 118.87(17) . . ?
C15 C14 C13 117.70(19) . . ?
C15 C14 C22 120.33(19) . . ?
C13 C14 C22 121.96(18) . . ?
C16 C15 C14 121.4(2) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.9(2) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C13 C18 C17 117.46(18) . . ?
C13 C18 C19 121.76(18) . . ?
C17 C18 C19 120.76(18) . . ?
C18 C19 C20 111.6(2) . . ?
C18 C19 C21 111.90(18) . . ?
C20 C19 C21 109.24(18) . . ?
C18 C19 H19 108.0 . . ?
C20 C19 H19 108.0 . . ?
C21 C19 H19 108.0 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C14 111.54(19) . . ?
C23 C22 C24 108.9(2) . . ?
C14 C22 C24 110.3(2) . . ?
C23 C22 H22 108.7 . . ?
C14 C22 H22 108.7 . . ?
C24 C22 H22 108.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C2 N1 C1 N2 -0.5(2) . . . . ?
C4 N1 C1 N2 176.94(16) . . . . ?
C2 N1 C1 Cu 178.31(14) . . . . ?
C4 N1 C1 Cu -4.3(3) . . . . ?
C3 N2 C1 N1 0.0(2) . . . . ?
C13 N2 C1 N1 -177.30(16) . . . . ?
C3 N2 C1 Cu -178.81(14) . . . . ?
C13 N2 C1 Cu 3.9(3) . . . . ?
N3 Cu C1 N1 -123.62(16) 2_646 . . . ?
Cl1 Cu C1 N1 58.6(2) . . . . ?
N3 Cu C1 N2 54.91(19) 2_646 . . . ?
Cl1 Cu C1 N2 -122.89(15) . . . . ?
C1 N1 C2 C3 0.8(2) . . . . ?
C4 N1 C2 C3 -176.61(17) . . . . ?
N1 C2 C3 N2 -0.7(2) . . . . ?
C1 N2 C3 C2 0.5(2) . . . . ?
C13 N2 C3 C2 177.73(17) . . . . ?
C1 N1 C4 C5 -130.41(18) . . . . ?
C2 N1 C4 C5 46.7(2) . . . . ?
C9 N3 C5 C6 -0.3(3) . . . . ?
Cu N3 C5 C6 179.28(14) 2_656 . . . ?
C9 N3 C5 C4 179.99(16) . . . . ?
Cu N3 C5 C4 -0.4(2) 2_656 . . . ?
N1 C4 C5 N3 -119.73(17) . . . . ?
N1 C4 C5 C6 60.6(2) . . . . ?
N3 C5 C6 C7 2.0(3) . . . . ?
C4 C5 C6 C7 -178.34(17) . . . . ?
N3 C5 C6 C10 -178.2(2) . . . . ?
C4 C5 C6 C10 1.5(3) . . . . ?
C12 O1 C7 C8 -83.1(2) . . . . ?
C12 O1 C7 C6 100.1(2) . . . . ?
C5 C6 C7 O1 175.06(17) . . . . ?
C10 C6 C7 O1 -4.7(3) . . . . ?
C5 C6 C7 C8 -1.7(3) . . . . ?
C10 C6 C7 C8 178.5(2) . . . . ?
O1 C7 C8 C9 -176.79(17) . . . . ?
C6 C7 C8 C9 -0.1(3) . . . . ?
O1 C7 C8 C11 2.2(3) . . . . ?
C6 C7 C8 C11 178.91(19) . . . . ?
C5 N3 C9 C8 -1.7(3) . . . . ?
Cu N3 C9 C8 178.66(16) 2_656 . . . ?
C7 C8 C9 N3 1.9(3) . . . . ?
C11 C8 C9 N3 -177.09(19) . . . . ?
C1 N2 C13 C18 -98.7(2) . . . . ?
C3 N2 C13 C18 84.4(2) . . . . ?
C1 N2 C13 C14 79.9(2) . . . . ?
C3 N2 C13 C14 -97.1(2) . . . . ?
C18 C13 C14 C15 -2.1(3) . . . . ?
N2 C13 C14 C15 179.39(17) . . . . ?
C18 C13 C14 C22 176.68(19) . . . . ?
N2 C13 C14 C22 -1.8(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C22 C14 C15 C16 -178.6(2) . . . . ?
C14 C15 C16 C17 1.2(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C14 C13 C18 C17 2.6(3) . . . . ?
N2 C13 C18 C17 -178.93(16) . . . . ?
C14 C13 C18 C19 -176.01(18) . . . . ?
N2 C13 C18 C19 2.5(3) . . . . ?
C16 C17 C18 C13 -1.1(3) . . . . ?
C16 C17 C18 C19 177.46(19) . . . . ?
C13 C18 C19 C20 145.8(2) . . . . ?
C17 C18 C19 C20 -32.7(3) . . . . ?
C13 C18 C19 C21 -91.5(2) . . . . ?
C17 C18 C19 C21 90.0(2) . . . . ?
C15 C14 C22 C23 -83.6(3) . . . . ?
C13 C14 C22 C23 97.7(2) . . . . ?
C15 C14 C22 C24 37.7(3) . . . . ?
C13 C14 C22 C24 -141.1(2) . . . . ?

_refine_diff_density_max         1.648
_refine_diff_density_min         -0.754
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_2023_CX37_a
_database_code_depnum_ccdc_archive 'CCDC 2264868'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C21 H25 Br Cu N3 O'
_chemical_formula_weight         478.89

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.5159(16)
_cell_length_b                   9.8890(11)
_cell_length_c                   14.8049(16)
_cell_angle_alpha                90
_cell_angle_beta                 91.637(4)
_cell_angle_gamma                90
_cell_volume                     2124.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1870
_cell_measurement_theta_min      2.5043
_cell_measurement_theta_max      26.7864
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_F_000             976
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.196
_exptl_crystal_size_mid          0.153
_exptl_crystal_size_min          0.149
_exptl_absorpt_coefficient_mu    2.924
_shelx_estimated_absorpt_T_min   0.598
_shelx_estimated_absorpt_T_max   0.670
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.6706
_exptl_absorpt_correction_T_max  0.7325
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            81002
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         30.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6476
_reflns_number_gt                5126
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0370P)²+1.3533P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6476
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0798
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
Cu Cu 0.36645(2) 0.43428(2) 0.32247(2) 0.02052(6) Uani 1 1 d . . . . .
Br1 Br 0.33846(2) 0.51327(2) 0.46886(2) 0.03533(7) Uani 1 1 d . . . . .
O1 O -0.07724(10) 0.39141(14) 0.16264(10) 0.0302(3) Uani 1 1 d . . . . .
N1 N 0.27588(10) 0.60827(15) 0.18177(10) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.39522(11) 0.50873(16) 0.13378(11) 0.0227(3) Uani 1 1 d . . . . .
N3 N 0.07121(10) 0.74848(15) 0.16319(10) 0.0193(3) Uani 1 1 d . . . . .
C1 C 0.34242(12) 0.51850(17) 0.20771(12) 0.0197(3) Uani 1 1 d . . . . .
C2 C 0.28767(13) 0.6548(2) 0.09461(13) 0.0261(4) Uani 1 1 d . . . . .
H2 H 0.250125 0.718458 0.062688 0.031 Uiso 1 1 calc R U . . .
C3 C 0.36291(14) 0.5918(2) 0.06409(13) 0.0280(4) Uani 1 1 d . . . . .
H3 H 0.388809 0.602101 0.006285 0.034 Uiso 1 1 calc R U . . .
C4 C 0.20325(12) 0.65242(18) 0.24189(12) 0.0208(3) Uani 1 1 d . . . . .
H4A H 0.213028 0.748820 0.257435 0.025 Uiso 1 1 calc R U . . .
H4B H 0.207685 0.599497 0.298611 0.025 Uiso 1 1 calc R U . . .
C5 C 0.10799(12) 0.63531(17) 0.19981(12) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.06155(13) 0.51181(18) 0.19955(13) 0.0235(4) Uani 1 1 d . . . . .
C7 C -0.02672(13) 0.50895(18) 0.15996(13) 0.0229(4) Uani 1 1 d . . . . .
C8 C -0.06605(13) 0.6245(2) 0.12167(13) 0.0259(4) Uani 1 1 d . . . . .
C9 C -0.01336(13) 0.74167(19) 0.12529(13) 0.0245(4) Uani 1 1 d . . . . .
H9 H -0.038902 0.821644 0.099326 0.029 Uiso 1 1 calc R U . . .
C10 C 0.10251(16) 0.3863(2) 0.24215(19) 0.0414(6) Uani 1 1 d . . . . .
H10A H 0.055091 0.338554 0.275550 0.062 Uiso 1 1 calc R U . . .
H10B H 0.153353 0.411598 0.283738 0.062 Uiso 1 1 calc R U . . .
H10C H 0.125734 0.327009 0.194877 0.062 Uiso 1 1 calc R U . . .
C11 C -0.16179(16) 0.6255(3) 0.07976(18) 0.0433(6) Uani 1 1 d . . . . .
H11A H -0.182415 0.719093 0.071340 0.065 Uiso 1 1 calc R U . . .
H11B H -0.203912 0.578222 0.119591 0.065 Uiso 1 1 calc R U . . .
H11C H -0.161362 0.579684 0.021061 0.065 Uiso 1 1 calc R U . . .
C12 C -0.06844(19) 0.3087(2) 0.08339(17) 0.0449(6) Uani 1 1 d . . . . .
H12A H -0.110495 0.231429 0.086629 0.067 Uiso 1 1 calc R U . . .
H12B H -0.004898 0.275951 0.080145 0.067 Uiso 1 1 calc R U . . .
H12C H -0.083933 0.362354 0.029418 0.067 Uiso 1 1 calc R U . . .
C13 C 0.46987(13) 0.41289(19) 0.13013(13) 0.0236(4) Uani 1 1 d . . . . .
C14 C 0.45449(14) 0.2897(2) 0.08612(13) 0.0271(4) Uani 1 1 d . . . . .
C15 C 0.52353(16) 0.1929(2) 0.09271(15) 0.0362(5) Uani 1 1 d . . . . .
H15 H 0.514392 0.108456 0.063237 0.043 Uiso 1 1 calc R U . . .
C16 C 0.60532(16) 0.2153(3) 0.14083(15) 0.0397(6) Uani 1 1 d . . . . .
C17 C 0.61913(15) 0.3402(3) 0.18045(15) 0.0403(6) Uani 1 1 d . . . . .
H17 H 0.676189 0.357895 0.211207 0.048 Uiso 1 1 calc R U . . .
C18 C 0.55220(14) 0.4412(2) 0.17688(14) 0.0315(4) Uani 1 1 d . . . . .
C19 C 0.56781(17) 0.5743(3) 0.2244(2) 0.0517(7) Uani 1 1 d . . . . .
H19A H 0.546195 0.648186 0.185139 0.078 Uiso 1 1 calc R U . . .
H19B H 0.633734 0.585764 0.238434 0.078 Uiso 1 1 calc R U . . .
H19C H 0.533665 0.575413 0.280552 0.078 Uiso 1 1 calc R U . . .
C20 C 0.36619(16) 0.2626(3) 0.03328(17) 0.0413(5) Uani 1 1 d . . . . .
H20A H 0.313689 0.291513 0.068721 0.062 Uiso 1 1 calc R U . . .
H20B H 0.361076 0.165677 0.020423 0.062 Uiso 1 1 calc R U . . .
H20C H 0.366354 0.313125 -0.023675 0.062 Uiso 1 1 calc R U . . .
C21 C 0.6768(2) 0.1045(3) 0.1500(2) 0.0633(9) Uani 1 1 d . . . . .
H21A H 0.650549 0.027144 0.181704 0.095 Uiso 1 1 calc R U . . .
H21B H 0.730655 0.138379 0.184376 0.095 Uiso 1 1 calc R U . . .
H21C H 0.695471 0.076020 0.089794 0.095 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
Cu C1 1.9152(18) . ?
Cu N3 2.0565(15) 2_545 ?
Cu Br1 2.3500(4) . ?
O1 C7 1.376(2) . ?
O1 C12 1.439(3) . ?
N1 C1 1.359(2) . ?
N1 C2 1.385(2) . ?
N1 C4 1.466(2) . ?
N2 C1 1.357(2) . ?
N2 C3 1.390(2) . ?
N2 C13 1.442(2) . ?
N3 C9 1.337(2) . ?
N3 C5 1.347(2) . ?
C2 C3 1.346(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.510(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.395(2) . ?
C6 C7 1.394(3) . ?
C6 C10 1.507(3) . ?
C7 C8 1.391(3) . ?
C8 C9 1.389(3) . ?
C8 C11 1.506(3) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.392(3) . ?
C13 C14 1.396(3) . ?
C14 C15 1.387(3) . ?
C14 C20 1.506(3) . ?
C15 C16 1.385(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.379(4) . ?
C16 C21 1.513(3) . ?
C17 C18 1.393(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.506(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C1 Cu N3 123.27(7) . 2_545 ?
C1 Cu Br1 129.92(5) . . ?
N3 Cu Br1 106.79(4) 2_545 . ?
C7 O1 C12 113.39(16) . . ?
C1 N1 C2 111.98(15) . . ?
C1 N1 C4 122.73(15) . . ?
C2 N1 C4 125.25(15) . . ?
C1 N2 C3 111.72(15) . . ?
C1 N2 C13 121.29(15) . . ?
C3 N2 C13 126.78(16) . . ?
C9 N3 C5 118.40(15) . . ?
C9 N3 Cu 118.98(12) . 2 ?
C5 N3 Cu 122.18(12) . 2 ?
N2 C1 N1 103.40(15) . . ?
N2 C1 Cu 126.27(13) . . ?
N1 C1 Cu 130.14(13) . . ?
C3 C2 N1 106.39(16) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 106.50(17) . . ?
C2 C3 H3 126.8 . . ?
N2 C3 H3 126.8 . . ?
N1 C4 C5 112.47(14) . . ?
N1 C4 H4A 109.1 . . ?
C5 C4 H4A 109.1 . . ?
N1 C4 H4B 109.1 . . ?
C5 C4 H4B 109.1 . . ?
H4A C4 H4B 107.8 . . ?
N3 C5 C6 122.70(16) . . ?
N3 C5 C4 114.88(15) . . ?
C6 C5 C4 122.42(16) . . ?
C7 C6 C5 117.21(16) . . ?
C7 C6 C10 120.41(17) . . ?
C5 C6 C10 122.36(17) . . ?
O1 C7 C8 119.54(17) . . ?
O1 C7 C6 119.30(17) . . ?
C8 C7 C6 121.09(16) . . ?
C9 C8 C7 116.78(17) . . ?
C9 C8 C11 120.76(18) . . ?
C7 C8 C11 122.44(18) . . ?
N3 C9 C8 123.81(17) . . ?
N3 C9 H9 118.1 . . ?
C8 C9 H9 118.1 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 122.05(18) . . ?
C18 C13 N2 118.99(18) . . ?
C14 C13 N2 118.73(17) . . ?
C15 C14 C13 117.62(19) . . ?
C15 C14 C20 121.1(2) . . ?
C13 C14 C20 121.31(19) . . ?
C16 C15 C14 122.2(2) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C15 118.3(2) . . ?
C17 C16 C21 121.3(2) . . ?
C15 C16 C21 120.4(3) . . ?
C16 C17 C18 122.2(2) . . ?
C16 C17 H17 118.9 . . ?
C18 C17 H17 118.9 . . ?
C13 C18 C17 117.5(2) . . ?
C13 C18 C19 121.6(2) . . ?
C17 C18 C19 120.9(2) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C3 N2 C1 N1 0.8(2) . . . . ?
C13 N2 C1 N1 -174.30(16) . . . . ?
C3 N2 C1 Cu -174.60(14) . . . . ?
C13 N2 C1 Cu 10.3(3) . . . . ?
C2 N1 C1 N2 -0.9(2) . . . . ?
C4 N1 C1 N2 -178.72(15) . . . . ?
C2 N1 C1 Cu 174.21(14) . . . . ?
C4 N1 C1 Cu -3.6(3) . . . . ?
C1 N1 C2 C3 0.7(2) . . . . ?
C4 N1 C2 C3 178.47(17) . . . . ?
N1 C2 C3 N2 -0.2(2) . . . . ?
C1 N2 C3 C2 -0.4(2) . . . . ?
C13 N2 C3 C2 174.38(18) . . . . ?
C1 N1 C4 C5 -127.37(17) . . . . ?
C2 N1 C4 C5 55.1(2) . . . . ?
C9 N3 C5 C6 0.1(3) . . . . ?
Cu N3 C5 C6 172.42(14) 2 . . . ?
C9 N3 C5 C4 -179.44(15) . . . . ?
Cu N3 C5 C4 -7.2(2) 2 . . . ?
N1 C4 C5 N3 -98.64(18) . . . . ?
N1 C4 C5 C6 81.8(2) . . . . ?
N3 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 C7 178.98(16) . . . . ?
N3 C5 C6 C10 -178.9(2) . . . . ?
C4 C5 C6 C10 0.7(3) . . . . ?
C12 O1 C7 C8 88.9(2) . . . . ?
C12 O1 C7 C6 -94.2(2) . . . . ?
C5 C6 C7 O1 -176.33(16) . . . . ?
C10 C6 C7 O1 2.0(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C10 C6 C7 C8 178.9(2) . . . . ?
O1 C7 C8 C9 176.69(17) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
O1 C7 C8 C11 -2.0(3) . . . . ?
C6 C7 C8 C11 -179.0(2) . . . . ?
C5 N3 C9 C8 0.3(3) . . . . ?
Cu N3 C9 C8 -172.27(15) 2 . . . ?
C7 C8 C9 N3 -0.2(3) . . . . ?
C11 C8 C9 N3 178.5(2) . . . . ?
C1 N2 C13 C18 -76.8(2) . . . . ?
C3 N2 C13 C18 108.9(2) . . . . ?
C1 N2 C13 C14 97.8(2) . . . . ?
C3 N2 C13 C14 -76.4(2) . . . . ?
C18 C13 C14 C15 2.0(3) . . . . ?
N2 C13 C14 C15 -172.48(17) . . . . ?
C18 C13 C14 C20 -178.0(2) . . . . ?
N2 C13 C14 C20 7.6(3) . . . . ?
C13 C14 C15 C16 0.0(3) . . . . ?
C20 C14 C15 C16 180.0(2) . . . . ?
C14 C15 C16 C17 -2.4(3) . . . . ?
C14 C15 C16 C21 177.0(2) . . . . ?
C15 C16 C17 C18 2.9(3) . . . . ?
C21 C16 C17 C18 -176.5(2) . . . . ?
C14 C13 C18 C17 -1.5(3) . . . . ?
N2 C13 C18 C17 172.93(18) . . . . ?
C14 C13 C18 C19 -179.8(2) . . . . ?
N2 C13 C18 C19 -5.3(3) . . . . ?
C16 C17 C18 C13 -1.0(3) . . . . ?
C16 C17 C18 C19 177.2(2) . . . . ?

_refine_diff_density_max         1.070
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_2023i_CX9_b
_database_code_depnum_ccdc_archive 'CCDC 2266447'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C22 H25 Cu N4 O S'
_chemical_formula_weight         457.06

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'
S S 0.1246 0.1234 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.7265(16)
_cell_length_b                   10.3870(14)
_cell_length_c                   18.401(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.032(4)
_cell_angle_gamma                90
_cell_volume                     2164.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2585
_cell_measurement_theta_min      2.4422
_cell_measurement_theta_max      28.5309

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.999
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.126
_shelx_estimated_absorpt_T_min   0.399
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.4501
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            74975
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.292
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4966
_reflns_number_gt                4169
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2019/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2019/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0401P)²+1.2771P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4966
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0298
_refine_ls_wR_factor_ref         0.0831
_refine_ls_wR_factor_gt          0.0775
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu 0.34415(2) 0.56054(2) 0.84918(2) 0.02446(8) Uani 1 1 d . . . . .
S1 S 0.69589(5) 0.55000(7) 0.78273(4) 0.05485(18) Uani 1 1 d . . . . .
N1 N 0.16407(12) 0.38776(14) 0.75680(8) 0.0226(3) Uani 1 1 d . . . . .
N2 N 0.09595(12) 0.49022(15) 0.83683(8) 0.0239(3) Uani 1 1 d . . . . .
N3 N 0.14941(13) 0.23883(14) 0.59651(8) 0.0257(3) Uani 1 1 d . . . . .
N4 N 0.50508(15) 0.53261(17) 0.84405(11) 0.0390(4) Uani 1 1 d . . . . .
C1 C 0.19547(15) 0.47628(16) 0.81283(10) 0.0215(3) Uani 1 1 d . . . . .
C2 C 0.04854(16) 0.34653(18) 0.74662(10) 0.0284(4) Uani 1 1 d . . . . .
H2 H 0.007820 0.284912 0.711120 0.034 Uiso 1 1 calc R U . . .
C3 C 0.00570(16) 0.41127(19) 0.79707(11) 0.0304(4) Uani 1 1 d . . . . .
H3 H -0.071493 0.404309 0.804141 0.036 Uiso 1 1 calc R U . . .
C4 C 0.24534(15) 0.33747(17) 0.71522(10) 0.0268(4) Uani 1 1 d . . . . .
H4A H 0.262327 0.246014 0.728982 0.032 Uiso 1 1 calc R U . . .
H4B H 0.320705 0.385471 0.730681 0.032 Uiso 1 1 calc R U . . .
C5 C 0.19835(17) 0.34724(17) 0.63131(11) 0.0283(4) Uani 1 1 d . . . . .
C9 C 0.10815(19) 0.24093(19) 0.52168(11) 0.0352(4) Uani 1 1 d . . . . .
H9 H 0.059828 0.172972 0.496114 0.042 Uiso 1 1 calc R U . A 1
C13 C 0.08751(15) 0.57677(17) 0.89674(10) 0.0244(4) Uani 1 1 d . . . . .
C14 C 0.02823(16) 0.69311(18) 0.87795(11) 0.0292(4) Uani 1 1 d . . . . .
C15 C 0.02285(19) 0.77543(19) 0.93613(12) 0.0372(5) Uani 1 1 d . . . . .
H15 H -0.017771 0.855005 0.924645 0.045 Uiso 1 1 calc R U . . .
C16 C 0.07520(19) 0.74492(19) 1.01083(12) 0.0374(5) Uani 1 1 d . . . . .
C17 C 0.13352(18) 0.62780(19) 1.02706(11) 0.0331(4) Uani 1 1 d . . . . .
H17 H 0.169277 0.606181 1.078051 0.040 Uiso 1 1 calc R U . . .
C18 C 0.14101(16) 0.54142(17) 0.97085(10) 0.0268(4) Uani 1 1 d . . . . .
C19 C 0.20534(19) 0.41575(19) 0.99072(12) 0.0360(4) Uani 1 1 d . . . . .
H19A H 0.283641 0.421981 0.981267 0.054 Uiso 1 1 calc R U . . .
H19B H 0.160359 0.346708 0.959812 0.054 Uiso 1 1 calc R U . . .
H19C H 0.213926 0.396698 1.044035 0.054 Uiso 1 1 calc R U . . .
C20 C -0.02848(19) 0.7298(2) 0.79738(12) 0.0403(5) Uani 1 1 d . . . . .
H20A H 0.024591 0.707484 0.766025 0.060 Uiso 1 1 calc R U . . .
H20B H -0.043722 0.822718 0.794292 0.060 Uiso 1 1 calc R U . . .
H20C H -0.103159 0.683220 0.779466 0.060 Uiso 1 1 calc R U . . .
C21 C 0.0672(3) 0.8368(2) 1.07317(15) 0.0573(7) Uani 1 1 d . . . . .
H21A H 0.085284 0.924354 1.059700 0.086 Uiso 1 1 calc R U . . .
H21B H 0.123970 0.811087 1.120029 0.086 Uiso 1 1 calc R U . . .
H21C H -0.012845 0.834496 1.080134 0.086 Uiso 1 1 calc R U . . .
C22 C 0.58309(17) 0.53858(18) 0.81862(12) 0.0348(4) Uani 1 1 d . . . . .
O1A O 0.2333(3) 0.5573(3) 0.48567(17) 0.0472(11) Uani 0.516(5) 1 d . . P B 1
C6A C 0.2311(5) 0.4539(6) 0.5982(3) 0.0256(10) Uani 0.516(5) 1 d . . P B 1
C7A C 0.1964(5) 0.4534(4) 0.5196(2) 0.0292(9) Uani 0.516(5) 1 d . . P B 1
C9A C 0.1013(6) 0.3308(5) 0.3961(3) 0.0443(12) Uani 0.516(5) 1 d . . P B 1
H9A H 0.076813 0.241593 0.383613 0.066 Uiso 0.516(5) 1 calc R U P B 1
H9B H 0.168135 0.351723 0.375469 0.066 Uiso 0.516(5) 1 calc R U P B 1
H9C H 0.035287 0.388806 0.374493 0.066 Uiso 0.516(5) 1 calc R U P B 1
C10A C 0.2942(5) 0.5692(4) 0.6406(3) 0.0362(11) Uani 0.516(5) 1 d . . P B 1
H10A H 0.268301 0.582022 0.686627 0.054 Uiso 0.516(5) 1 calc R U P B 1
H10B H 0.275497 0.646071 0.608842 0.054 Uiso 0.516(5) 1 calc R U P B 1
H10C H 0.379595 0.554199 0.653787 0.054 Uiso 0.516(5) 1 calc R U P B 1
C11A C 0.1379(5) 0.3469(6) 0.4808(4) 0.0296(12) Uani 0.516(5) 1 d . . P B 1
C12A C 0.1884(11) 0.6033(8) 0.4257(4) 0.063(3) Uani 0.516(5) 1 d . . P B 1
H12A H 0.225576 0.686318 0.421008 0.095 Uiso 0.516(5) 1 calc R U P B 1
H12B H 0.103931 0.616222 0.420724 0.095 Uiso 0.516(5) 1 calc R U P B 1
H12C H 0.198756 0.545126 0.385929 0.095 Uiso 0.516(5) 1 calc R U P B 1
O1B O 0.1135(4) 0.5717(3) 0.4680(2) 0.0452(11) Uani 0.484(5) 1 d . . P B 2
C6B C 0.1816(5) 0.4650(5) 0.5862(4) 0.0261(11) Uani 0.484(5) 1 d . . P B 2
C7B C 0.1285(6) 0.4593(4) 0.5081(2) 0.0299(10) Uani 0.484(5) 1 d . . P B 2
C8B C 0.0872(5) 0.3439(7) 0.4735(4) 0.0304(13) Uani 0.484(5) 1 d . . P B 2
C10B C 0.2279(6) 0.5898(5) 0.6241(3) 0.0391(12) Uani 0.484(5) 1 d . . P B 2
H10D H 0.313743 0.593129 0.632061 0.059 Uiso 0.484(5) 1 calc R U P B 2
H10E H 0.208453 0.595470 0.672646 0.059 Uiso 0.484(5) 1 calc R U P B 2
H10F H 0.191473 0.661968 0.592086 0.059 Uiso 0.484(5) 1 calc R U P B 2
C11B C 0.0306(7) 0.3342(6) 0.3897(3) 0.0494(15) Uani 0.484(5) 1 d . . P B 2
H11A H -0.019872 0.257682 0.379477 0.074 Uiso 0.484(5) 1 calc R U P B 2
H11B H 0.092310 0.327542 0.362783 0.074 Uiso 0.484(5) 1 calc R U P B 2
H11C H -0.017206 0.411207 0.372791 0.074 Uiso 0.484(5) 1 calc R U P B 2
C12B C 0.1674(16) 0.6193(17) 0.4300(9) 0.135(7) Uani 0.484(5) 1 d . . P B 2
H12D H 0.156700 0.569538 0.383491 0.203 Uiso 0.484(5) 1 calc R U P B 2
H12E H 0.251332 0.620721 0.456897 0.203 Uiso 0.484(5) 1 calc R U P B 2
H12F H 0.139533 0.707583 0.417803 0.203 Uiso 0.484(5) 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu C1 1.9101(17) . ?
Cu N4 1.9357(17) . ?
Cu N3 2.0963(15) 2_556 ?
S1 C22 1.629(2) . ?
N1 C1 1.359(2) . ?
N1 C2 1.386(2) . ?
N1 C4 1.465(2) . ?
N2 C1 1.358(2) . ?
N2 C3 1.388(2) . ?
N2 C13 1.446(2) . ?
N3 C9 1.336(2) . ?
N3 C5 1.348(2) . ?
N4 C22 1.132(3) . ?
C2 C3 1.345(3) . ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.502(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6A 1.366(6) . ?
C5 C6B 1.462(6) . ?
C9 C8B 1.370(7) . ?
C9 C11A 1.426(7) . ?
C9 H9 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C18 1.394(3) . ?
C14 C15 1.384(3) . ?
C14 C20 1.508(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 C21 1.514(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.505(3) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O1A C12A 1.193(10) . ?
O1A C7A 1.372(5) . ?
C6A C7A 1.397(7) . ?
C6A C10A 1.514(7) . ?
C7A C11A 1.396(8) . ?
C9A C11A 1.515(8) . ?
C9A H9A 0.9800 . ?
C9A H9B 0.9800 . ?
C9A H9C 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O1B C12B 1.168(18) . ?
O1B C7B 1.368(5) . ?
C6B C7B 1.412(8) . ?
C6B C10B 1.504(8) . ?
C7B C8B 1.384(8) . ?
C8B C11B 1.515(8) . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11A 0.9800 . ?
C11B H11B 0.9800 . ?
C11B H11C 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 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
C1 Cu N4 136.65(7) . . ?
C1 Cu N3 119.24(7) . 2_556 ?
N4 Cu N3 103.92(7) . 2_556 ?
C1 N1 C2 112.00(14) . . ?
C1 N1 C4 123.55(14) . . ?
C2 N1 C4 124.38(15) . . ?
C1 N2 C3 111.57(15) . . ?
C1 N2 C13 123.28(14) . . ?
C3 N2 C13 125.15(15) . . ?
C9 N3 C5 118.15(16) . . ?
C9 N3 Cu 117.67(13) . 2_546 ?
C5 N3 Cu 123.59(12) . 2_546 ?
C22 N4 Cu 156.13(19) . . ?
N2 C1 N1 103.43(14) . . ?
N2 C1 Cu 128.34(13) . . ?
N1 C1 Cu 128.23(12) . . ?
C3 C2 N1 106.21(16) . . ?
C3 C2 H2 126.9 . . ?
N1 C2 H2 126.9 . . ?
C2 C3 N2 106.80(16) . . ?
C2 C3 H3 126.6 . . ?
N2 C3 H3 126.6 . . ?
N1 C4 C5 113.45(14) . . ?
N1 C4 H4A 108.9 . . ?
C5 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
N3 C5 C6A 126.8(3) . . ?
N3 C5 C6B 116.8(3) . . ?
N3 C5 C4 115.43(16) . . ?
C6A C5 C4 116.3(3) . . ?
C6B C5 C4 126.8(3) . . ?
N3 C9 C8B 129.5(3) . . ?
N3 C9 C11A 118.9(3) . . ?
N3 C9 H9 120.6 . . ?
C11A C9 H9 120.6 . . ?
C14 C13 C18 122.71(17) . . ?
C14 C13 N2 118.62(16) . . ?
C18 C13 N2 118.66(16) . . ?
C15 C14 C13 117.65(18) . . ?
C15 C14 C20 120.47(18) . . ?
C13 C14 C20 121.88(18) . . ?
C14 C15 C16 121.83(19) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C17 118.63(18) . . ?
C15 C16 C21 120.5(2) . . ?
C17 C16 C21 120.9(2) . . ?
C18 C17 C16 121.87(19) . . ?
C18 C17 H17 119.1 . . ?
C16 C17 H17 119.1 . . ?
C17 C18 C13 117.31(17) . . ?
C17 C18 C19 120.26(18) . . ?
C13 C18 C19 122.43(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 S1 178.9(2) . . ?
C12A O1A C7A 128.4(5) . . ?
C5 C6A C7A 114.8(4) . . ?
C5 C6A C10A 124.6(4) . . ?
C7A C6A C10A 120.6(5) . . ?
O1A C7A C11A 124.2(4) . . ?
O1A C7A C6A 115.3(4) . . ?
C11A C7A C6A 120.3(5) . . ?
C11A C9A H9A 109.5 . . ?
C11A C9A H9B 109.5 . . ?
H9A C9A H9B 109.5 . . ?
C11A C9A H9C 109.5 . . ?
H9A C9A H9C 109.5 . . ?
H9B C9A H9C 109.5 . . ?
C6A C10A H10A 109.5 . . ?
C6A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C6A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C7A C11A C9 119.8(5) . . ?
C7A C11A C9A 125.7(5) . . ?
C9 C11A C9A 114.5(5) . . ?
O1A C12A H12A 109.5 . . ?
O1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O1A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C12B O1B C7B 132.1(10) . . ?
C7B C6B C5 120.1(5) . . ?
C7B C6B C10B 121.2(5) . . ?
C5 C6B C10B 118.6(5) . . ?
O1B C7B C8B 120.7(5) . . ?
O1B C7B C6B 118.3(4) . . ?
C8B C7B C6B 120.9(5) . . ?
C9 C8B C7B 113.3(5) . . ?
C9 C8B C11B 124.4(6) . . ?
C7B C8B C11B 122.3(6) . . ?
C6B C10B H10D 109.5 . . ?
C6B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C6B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C8B C11B H11A 109.5 . . ?
C8B C11B H11B 109.5 . . ?
H11A C11B H11B 109.5 . . ?
C8B C11B H11C 109.5 . . ?
H11A C11B H11C 109.5 . . ?
H11B C11B H11C 109.5 . . ?
O1B C12B H12D 109.5 . . ?
O1B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
O1B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
C3 N2 C1 N1 0.6(2) . . . . ?
C13 N2 C1 N1 -179.70(15) . . . . ?
C3 N2 C1 Cu -179.31(14) . . . . ?
C13 N2 C1 Cu 0.4(3) . . . . ?
C2 N1 C1 N2 -0.62(19) . . . . ?
C4 N1 C1 N2 -177.57(15) . . . . ?
C2 N1 C1 Cu 179.26(13) . . . . ?
C4 N1 C1 Cu 2.3(2) . . . . ?
C1 N1 C2 C3 0.4(2) . . . . ?
C4 N1 C2 C3 177.36(17) . . . . ?
N1 C2 C3 N2 -0.1(2) . . . . ?
C1 N2 C3 C2 -0.3(2) . . . . ?
C13 N2 C3 C2 179.95(17) . . . . ?
C1 N1 C4 C5 -127.85(17) . . . . ?
C2 N1 C4 C5 55.6(2) . . . . ?
C9 N3 C5 C6A -13.1(4) . . . . ?
Cu N3 C5 C6A 157.9(3) 2_546 . . . ?
C9 N3 C5 C6B 11.6(3) . . . . ?
Cu N3 C5 C6B -177.4(3) 2_546 . . . ?
C9 N3 C5 C4 -178.70(16) . . . . ?
Cu N3 C5 C4 -7.7(2) 2_546 . . . ?
N1 C4 C5 N3 -98.38(18) . . . . ?
N1 C4 C5 C6A 94.4(3) . . . . ?
N1 C4 C5 C6B 70.1(4) . . . . ?
C5 N3 C9 C8B -13.4(5) . . . . ?
Cu N3 C9 C8B 175.1(4) 2_546 . . . ?
C5 N3 C9 C11A 12.2(4) . . . . ?
Cu N3 C9 C11A -159.3(3) 2_546 . . . ?
C1 N2 C13 C14 103.0(2) . . . . ?
C3 N2 C13 C14 -77.3(2) . . . . ?
C1 N2 C13 C18 -75.8(2) . . . . ?
C3 N2 C13 C18 103.9(2) . . . . ?
C18 C13 C14 C15 -0.3(3) . . . . ?
N2 C13 C14 C15 -178.98(16) . . . . ?
C18 C13 C14 C20 179.66(17) . . . . ?
N2 C13 C14 C20 0.9(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C20 C14 C15 C16 -179.34(18) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C14 C15 C16 C21 -179.7(2) . . . . ?
C15 C16 C17 C18 0.2(3) . . . . ?
C21 C16 C17 C18 179.4(2) . . . . ?
C16 C17 C18 C13 0.1(3) . . . . ?
C16 C17 C18 C19 179.78(19) . . . . ?
C14 C13 C18 C17 -0.1(3) . . . . ?
N2 C13 C18 C17 178.67(16) . . . . ?
C14 C13 C18 C19 -179.76(18) . . . . ?
N2 C13 C18 C19 -1.0(3) . . . . ?
N3 C5 C6A C7A 8.0(6) . . . . ?
C4 C5 C6A C7A 173.5(3) . . . . ?
N3 C5 C6A C10A -175.1(4) . . . . ?
C4 C5 C6A C10A -9.7(6) . . . . ?
C12A O1A C7A C11A 32.8(10) . . . . ?
C12A O1A C7A C6A -153.0(7) . . . . ?
C5 C6A C7A O1A -177.2(4) . . . . ?
C10A C6A C7A O1A 5.8(7) . . . . ?
C5 C6A C7A C11A -2.8(7) . . . . ?
C10A C6A C7A C11A -179.8(5) . . . . ?
O1A C7A C11A C9 177.0(5) . . . . ?
C6A C7A C11A C9 3.2(7) . . . . ?
O1A C7A C11A C9A -2.7(8) . . . . ?
C6A C7A C11A C9A -176.6(5) . . . . ?
N3 C9 C11A C7A -8.0(6) . . . . ?
N3 C9 C11A C9A 171.8(3) . . . . ?
N3 C5 C6B C7B -7.2(6) . . . . ?
C4 C5 C6B C7B -175.5(4) . . . . ?
N3 C5 C6B C10B 176.1(4) . . . . ?
C4 C5 C6B C10B 7.7(6) . . . . ?
C12B O1B C7B C8B -83.6(13) . . . . ?
C12B O1B C7B C6B 99.7(12) . . . . ?
C5 C6B C7B O1B 179.4(4) . . . . ?
C10B C6B C7B O1B -3.9(8) . . . . ?
C5 C6B C7B C8B 2.7(8) . . . . ?
C10B C6B C7B C8B 179.4(5) . . . . ?
N3 C9 C8B C7B 8.3(7) . . . . ?
N3 C9 C8B C11B -174.8(4) . . . . ?
O1B C7B C8B C9 -179.2(5) . . . . ?
C6B C7B C8B C9 -2.6(8) . . . . ?
O1B C7B C8B C11B 3.8(9) . . . . ?
C6B C7B C8B C11B -179.6(5) . . . . ?

_refine_diff_density_max         0.297
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.055

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

data_2023_CuNHCLip170K_a
_database_code_depnum_ccdc_archive 'CCDC 2264871'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C24 H25 Cl3 Cu N3'
_chemical_formula_weight         525.36

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

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

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

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

_cell_length_a                   13.8969(14)
_cell_length_b                   10.5381(11)
_cell_length_c                   17.6009(17)
_cell_angle_alpha                90
_cell_angle_beta                 108.907(3)
_cell_angle_gamma                90
_cell_volume                     2438.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    884
_cell_measurement_theta_min      2.4782
_cell_measurement_theta_max      28.0743
_cell_measurement_temperature    173.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.431
_exptl_crystal_F_000             1080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.196
_exptl_absorpt_coefficient_mu    1.241
_shelx_estimated_absorpt_T_min   0.643
_shelx_estimated_absorpt_T_max   0.793
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.7327
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            99517
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.264
_diffrn_reflns_theta_max         32.834
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8772
_reflns_number_gt                7009
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0402P)²+1.0651P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8772
_refine_ls_number_parameters     380
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0799
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
Cu Cu 0.36043(2) 0.14016(2) 0.34583(2) 0.01826(5) Uani 1 1 d . . . . .
Cl1 Cl 0.27283(3) 0.09439(4) 0.42926(2) 0.03593(9) Uani 1 1 d . . . . .
Cl2 Cl 1.02526(4) 0.84166(6) 0.57217(4) 0.06111(15) Uani 1 1 d . . . . .
Cl3 Cl 0.89084(6) 0.66769(7) 0.46035(4) 0.0754(2) Uani 1 1 d . . . . .
N1 N 0.32999(8) -0.06528(10) 0.22695(7) 0.01842(19) Uani 1 1 d . . . . .
N2 N 0.45423(8) 0.05303(10) 0.22600(7) 0.0194(2) Uani 1 1 d . . . . .
N3 N 0.09493(8) -0.17366(10) 0.13991(6) 0.01693(19) Uani 1 1 d . . . . .
C1 C 0.38414(9) 0.03780(11) 0.26405(7) 0.0177(2) Uani 1 1 d . . . . .
C2 C 0.36515(10) -0.11301(13) 0.16727(8) 0.0232(3) Uani 1 1 d . . . . .
H2 H 0.3348(14) -0.1831(19) 0.1366(11) 0.030(5) Uiso 1 1 d . . . . .
C3 C 0.44391(10) -0.03832(14) 0.16683(9) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.4865(14) -0.0412(18) 0.1362(11) 0.029(5) Uiso 1 1 d . . . . .
C4 C 0.24575(9) -0.11786(12) 0.24969(8) 0.0197(2) Uani 1 1 d . . . . .
H4A H 0.2518(13) -0.2061(18) 0.2531(10) 0.024(4) Uiso 1 1 d . . . . .
H4B H 0.2517(13) -0.0826(17) 0.3025(10) 0.024(4) Uiso 1 1 d . . . . .
C5 C 0.14286(9) -0.08408(11) 0.19086(8) 0.0186(2) Uani 1 1 d . . . . .
C6 C 0.10132(10) 0.03719(12) 0.19304(9) 0.0253(3) Uani 1 1 d . . . . .
H6 H 0.1356(15) 0.089(2) 0.2354(12) 0.037(5) Uiso 1 1 d . . . . .
C7 C 0.00799(10) 0.06961(12) 0.13996(9) 0.0251(3) Uani 1 1 d . . . . .
C8 C -0.04423(10) -0.02360(12) 0.08304(8) 0.0214(2) Uani 1 1 d . . . . .
C9 C -0.14084(11) -0.00285(15) 0.02440(9) 0.0283(3) Uani 1 1 d . . . . .
H9 H -0.1706(14) 0.0764(19) 0.0205(11) 0.032(5) Uiso 1 1 d . . . . .
C10 C -0.18902(12) -0.09808(17) -0.02612(10) 0.0343(3) Uani 1 1 d . . . . .
H10 H -0.2516(18) -0.083(2) -0.0639(13) 0.050(6) Uiso 1 1 d . . . . .
C11 C -0.14424(12) -0.21895(16) -0.02229(10) 0.0335(3) Uani 1 1 d . . . . .
H11 H -0.1780(16) -0.287(2) -0.0550(12) 0.041(5) Uiso 1 1 d . . . . .
C12 C -0.05000(11) -0.24126(14) 0.03221(8) 0.0255(3) Uani 1 1 d . . . . .
H12 H -0.0184(13) -0.3196(18) 0.0340(11) 0.025(4) Uiso 1 1 d . . . . .
C13 C 0.00135(9) -0.14485(12) 0.08557(8) 0.0188(2) Uani 1 1 d . . . . .
C14 C -0.03791(14) 0.19764(16) 0.14315(14) 0.0399(4) Uani 1 1 d . . . . .
H14A H -0.0994(19) 0.190(2) 0.1561(14) 0.054(6) Uiso 1 1 d . . . . .
H14B H -0.0579(18) 0.240(2) 0.0896(15) 0.056(7) Uiso 1 1 d . . . . .
H14C H 0.0059(19) 0.251(3) 0.1825(15) 0.067(8) Uiso 1 1 d . . . . .
C15 C 0.53076(9) 0.15112(12) 0.24693(8) 0.0190(2) Uani 1 1 d . . . . .
C16 C 0.62043(10) 0.12946(13) 0.31001(9) 0.0243(3) Uani 1 1 d . . . . .
C17 C 0.69192(11) 0.22709(16) 0.33020(9) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.7540(15) 0.2132(19) 0.3760(12) 0.036(5) Uiso 1 1 d . . . . .
C18 C 0.67583(12) 0.34221(15) 0.29034(10) 0.0298(3) Uani 1 1 d . . . . .
C19 C 0.58532(12) 0.36062(14) 0.22818(10) 0.0279(3) Uani 1 1 d . . . . .
H19 H 0.5742(15) 0.4362(19) 0.2022(12) 0.036(5) Uiso 1 1 d . . . . .
C20 C 0.51146(10) 0.26608(13) 0.20499(8) 0.0221(2) Uani 1 1 d . . . . .
C21 C 0.41412(12) 0.28813(17) 0.13753(10) 0.0323(3) Uani 1 1 d . . . . .
H21A H 0.4021(19) 0.373(2) 0.1254(15) 0.055(7) Uiso 1 1 d . . . . .
H21B H 0.3568(16) 0.258(2) 0.1536(12) 0.040(5) Uiso 1 1 d . . . . .
H21C H 0.4170(17) 0.245(2) 0.0895(14) 0.051(6) Uiso 1 1 d . . . . .
C22 C 0.63972(14) 0.00684(18) 0.35614(12) 0.0383(4) Uani 1 1 d . . . . .
H22A H 0.697(2) 0.010(3) 0.3948(18) 0.083(9) Uiso 1 1 d . . . . .
H22B H 0.639(2) -0.065(3) 0.3237(16) 0.071(8) Uiso 1 1 d . . . . .
H22C H 0.592(2) -0.008(3) 0.3805(17) 0.078(9) Uiso 1 1 d . . . . .
C23 C 0.75437(18) 0.4461(2) 0.31560(15) 0.0496(5) Uani 1 1 d . . . . .
H23A H 0.748(3) 0.486(4) 0.363(3) 0.136(15) Uiso 1 1 d . . . . .
H23B H 0.739(3) 0.511(4) 0.283(2) 0.111(13) Uiso 1 1 d . . . . .
H23C H 0.814(3) 0.423(3) 0.3088(18) 0.087(10) Uiso 1 1 d . . . . .
C24 C 0.91547(14) 0.8269(2) 0.48846(12) 0.0423(4) Uani 1 1 d . . . . .
H24A H 0.9308(18) 0.870(2) 0.4464(14) 0.052(7) Uiso 1 1 d . . . . .
H24B H 0.8582(18) 0.856(2) 0.5035(14) 0.048(6) Uiso 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
Cu C1 1.9108(12) . ?
Cu N3 2.0485(11) 2 ?
Cu Cl1 2.2427(4) . ?
Cl2 C24 1.751(2) . ?
Cl3 C24 1.752(2) . ?
N1 C1 1.3616(15) . ?
N1 C2 1.3884(17) . ?
N1 C4 1.4634(16) . ?
N2 C1 1.3586(16) . ?
N2 C3 1.3911(17) . ?
N2 C15 1.4427(15) . ?
N3 C5 1.3236(16) . ?
N3 C13 1.3755(16) . ?
C2 C3 1.3502(19) . ?
C4 C5 1.5112(17) . ?
C5 C6 1.4080(18) . ?
C6 C7 1.3735(19) . ?
C7 C8 1.4226(19) . ?
C7 C14 1.501(2) . ?
C8 C9 1.4205(19) . ?
C8 C13 1.4205(17) . ?
C9 C10 1.364(2) . ?
C10 C11 1.410(2) . ?
C11 C12 1.370(2) . ?
C12 C13 1.4103(19) . ?
C15 C16 1.3932(18) . ?
C15 C20 1.3987(18) . ?
C16 C17 1.3939(19) . ?
C16 C22 1.503(2) . ?
C17 C18 1.383(2) . ?
C18 C19 1.387(2) . ?
C18 C23 1.508(2) . ?
C19 C20 1.3933(19) . ?
C20 C21 1.501(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Cu N3 120.91(5) . 2 ?
C1 Cu Cl1 129.39(4) . . ?
N3 Cu Cl1 109.44(3) 2 . ?
C1 N1 C2 112.12(11) . . ?
C1 N1 C4 122.53(11) . . ?
C2 N1 C4 125.35(11) . . ?
C1 N2 C3 111.77(10) . . ?
C1 N2 C15 123.07(10) . . ?
C3 N2 C15 125.14(11) . . ?
C5 N3 C13 117.94(11) . . ?
C5 N3 Cu 122.28(8) . 2_545 ?
C13 N3 Cu 118.50(8) . 2_545 ?
N2 C1 N1 103.35(10) . . ?
N2 C1 Cu 129.11(9) . . ?
N1 C1 Cu 127.46(9) . . ?
C3 C2 N1 106.14(11) . . ?
C2 C3 N2 106.62(12) . . ?
N1 C4 C5 112.74(11) . . ?
N3 C5 C6 123.03(12) . . ?
N3 C5 C4 116.93(11) . . ?
C6 C5 C4 120.03(11) . . ?
C7 C6 C5 120.82(12) . . ?
C6 C7 C8 117.46(12) . . ?
C6 C7 C14 121.14(14) . . ?
C8 C7 C14 121.39(13) . . ?
C9 C8 C13 117.91(12) . . ?
C9 C8 C7 123.49(12) . . ?
C13 C8 C7 118.59(11) . . ?
C10 C9 C8 120.61(13) . . ?
C9 C10 C11 121.19(13) . . ?
C12 C11 C10 119.71(14) . . ?
C11 C12 C13 120.36(13) . . ?
N3 C13 C12 117.68(11) . . ?
N3 C13 C8 122.13(11) . . ?
C12 C13 C8 120.19(12) . . ?
C16 C15 C20 122.11(12) . . ?
C16 C15 N2 118.76(12) . . ?
C20 C15 N2 119.10(11) . . ?
C15 C16 C17 117.51(13) . . ?
C15 C16 C22 121.88(13) . . ?
C17 C16 C22 120.61(14) . . ?
C18 C17 C16 122.24(14) . . ?
C17 C18 C19 118.62(13) . . ?
C17 C18 C23 120.32(17) . . ?
C19 C18 C23 121.04(17) . . ?
C18 C19 C20 121.65(14) . . ?
C19 C20 C15 117.88(13) . . ?
C19 C20 C21 120.71(13) . . ?
C15 C20 C21 121.41(13) . . ?
Cl2 C24 Cl3 111.09(12) . . ?

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_2023_CX40_a
_database_code_depnum_ccdc_archive 'CCDC 2264869'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-07-25 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C44 H54 Cl4 Cu2 N12 O2'
_chemical_formula_weight         1051.87

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'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.2745(7)
_cell_length_b                   11.2131(7)
_cell_length_c                   11.3294(8)
_cell_angle_alpha                91.902(4)
_cell_angle_beta                 93.379(4)
_cell_angle_gamma                113.401(3)
_cell_volume                     1193.52(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    173(2)
_cell_measurement_theta_min      2.7295
_cell_measurement_theta_max      22.8869
_cell_measurement_reflns_used    1449

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.228
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    1.166
_shelx_estimated_absorpt_T_min   0.777
_shelx_estimated_absorpt_T_max   0.871
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.7961
_exptl_absorpt_correction_T_max  0.9215
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            92223
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         30.625
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7307
_reflns_number_gt                4788
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0913P)²+1.6021P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7307
_refine_ls_number_parameters     315
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1885
_refine_ls_wR_factor_gt          0.1604
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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
Cu Cu 0.52689(5) 0.49310(4) 0.60214(4) 0.03739(14) Uani 1 1 d . . . . .
Cl1 Cl 0.68002(19) 0.18023(16) 0.08742(19) 0.1117(7) Uani 1 1 d . . . . .
Cl2 Cl 0.79716(18) 0.42281(12) -0.02555(12) 0.0830(4) Uani 1 1 d . . . . .
N1 N 0.2731(3) 0.5539(2) 0.5552(2) 0.0299(5) Uani 1 1 d . . . . .
N2 N 0.5633(3) 0.2648(2) 0.4797(2) 0.0287(5) Uani 1 1 d . . . . .
N3 N 0.3723(3) 0.4159(3) 0.7200(2) 0.0351(6) Uani 1 1 d . . . . .
N4 N 0.7013(4) 0.5818(3) 0.7194(3) 0.0472(7) Uani 1 1 d . . . . .
N5 N 0.8119(3) 0.5729(3) 0.7158(2) 0.0351(6) Uani 1 1 d . . . . .
N6 N 0.9215(3) 0.5658(3) 0.7136(3) 0.0497(8) Uani 1 1 d . . . . .
C1 C 0.5956(3) 0.3957(3) 0.4837(3) 0.0309(6) Uani 1 1 d . . . . .
C2 C 0.2244(4) 0.6491(3) 0.5838(3) 0.0371(7) Uani 1 1 d . . . . .
H2 H 0.135661 0.636121 0.613752 0.045 Uiso 1 1 calc R U . . .
C3 C 0.6732(4) 0.2370(3) 0.4390(3) 0.0369(7) Uani 1 1 d . . . . .
H3 H 0.675483 0.153431 0.429108 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1944(4) 0.4154(3) 0.5708(3) 0.0372(7) Uani 1 1 d . . . . .
H4A H 0.215026 0.363881 0.507561 0.045 Uiso 1 1 calc R U . . .
H4B H 0.091120 0.394833 0.562736 0.045 Uiso 1 1 calc R U . . .
C5 C 0.2326(4) 0.3766(3) 0.6901(3) 0.0344(7) Uani 1 1 d . . . . .
C6 C 0.1285(4) 0.3024(3) 0.7612(3) 0.0409(8) Uani 1 1 d . . . . .
C7 C 0.1765(5) 0.2660(4) 0.8665(3) 0.0506(10) Uani 1 1 d . . . . .
C8 C 0.3196(5) 0.3097(4) 0.9022(3) 0.0466(9) Uani 1 1 d . . . . .
C9 C 0.4124(4) 0.3851(4) 0.8254(3) 0.0406(8) Uani 1 1 d . . . . .
H9 H 0.511327 0.417470 0.848465 0.049 Uiso 1 1 calc R U . . .
C10 C -0.0266(4) 0.2635(4) 0.7292(4) 0.0592(12) Uani 1 1 d . . . . .
H10A H -0.050304 0.225732 0.647536 0.089 Uiso 1 1 calc R U . . .
H10B H -0.049405 0.340221 0.736200 0.089 Uiso 1 1 calc R U . . .
H10C H -0.081741 0.198883 0.782967 0.089 Uiso 1 1 calc R U . . .
C11 C 0.3748(6) 0.2734(6) 1.0159(4) 0.0750(15) Uani 1 1 d . . . . .
H11A H 0.478386 0.303222 1.017602 0.112 Uiso 1 1 calc R U . . .
H11B H 0.331656 0.178656 1.020501 0.112 Uiso 1 1 calc R U . . .
H11C H 0.350037 0.314847 1.083580 0.112 Uiso 1 1 calc R U . . .
C13 C 0.4395(3) 0.1713(3) 0.5264(3) 0.0293(6) Uani 1 1 d . . . . .
C14 C 0.4489(4) 0.1480(3) 0.6467(3) 0.0326(6) Uani 1 1 d . . . . .
C15 C 0.3257(4) 0.0637(3) 0.6933(3) 0.0356(7) Uani 1 1 d . . . . .
H15 H 0.328374 0.048346 0.775230 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1992(4) 0.0014(3) 0.6237(3) 0.0356(7) Uani 1 1 d . . . . .
C17 C 0.1973(3) 0.0229(3) 0.5036(3) 0.0351(7) Uani 1 1 d . . . . .
H17 H 0.111742 -0.021268 0.454838 0.042 Uiso 1 1 calc R U . . .
C18 C 0.3167(3) 0.1070(3) 0.4528(3) 0.0307(6) Uani 1 1 d . . . . .
C19 C 0.3140(4) 0.1248(4) 0.3213(3) 0.0390(7) Uani 1 1 d . . . . .
H19A H 0.320096 0.212559 0.307269 0.059 Uiso 1 1 calc R U . . .
H19B H 0.225140 0.060252 0.282140 0.059 Uiso 1 1 calc R U . . .
H19C H 0.394965 0.113128 0.289265 0.059 Uiso 1 1 calc R U . . .
C20 C 0.5859(4) 0.2075(4) 0.7221(3) 0.0441(8) Uani 1 1 d . . . . .
H20A H 0.627514 0.301896 0.714692 0.066 Uiso 1 1 calc R U . . .
H20B H 0.651996 0.170430 0.696064 0.066 Uiso 1 1 calc R U . . .
H20C H 0.568176 0.189246 0.804976 0.066 Uiso 1 1 calc R U . . .
C21 C 0.0703(4) -0.0906(4) 0.6778(4) 0.0501(10) Uani 1 1 d . . . . .
H21A H 0.033394 -0.041172 0.729038 0.075 Uiso 1 1 calc R U . . .
H21B H 0.096188 -0.150852 0.724802 0.075 Uiso 1 1 calc R U . . .
H21C H -0.002844 -0.140007 0.614838 0.075 Uiso 1 1 calc R U . . .
C22 C 0.7746(7) 0.3554(6) 0.1070(5) 0.092(2) Uani 1 1 d . . . . .
H22A H 0.720250 0.391948 0.155128 0.111 Uiso 1 1 calc R U . . .
H22B H 0.868555 0.376856 0.149982 0.111 Uiso 1 1 calc R U . . .
O1A O 0.0704(14) 0.2301(15) 0.9540(12) 0.051(4) Uani 0.270(13) 1 d . . P A 1
C12A C 0.051(4) 0.1047(19) 0.985(3) 0.131(15) Uani 0.270(13) 1 d . . P A 1
H12A H 0.132128 0.109361 1.037587 0.197 Uiso 0.270(13) 1 calc R U P A 1
H12B H 0.044321 0.050737 0.912819 0.197 Uiso 0.270(13) 1 calc R U P A 1
H12C H -0.036634 0.066250 1.024959 0.197 Uiso 0.270(13) 1 calc R U P A 1
O1B O 0.0784(6) 0.1689(6) 0.9262(4) 0.0574(16) Uani 0.730(13) 1 d . . P A 2
C12B C 0.0396(10) 0.2167(9) 1.0300(7) 0.087(3) Uani 0.730(13) 1 d . . P A 2
H12D H 0.125025 0.265368 1.082615 0.130 Uiso 0.730(13) 1 calc R U P A 2
H12E H -0.025485 0.143530 1.070817 0.130 Uiso 0.730(13) 1 calc R U P A 2
H12F H -0.007727 0.274377 1.008192 0.130 Uiso 0.730(13) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu C1 2.030(3) . ?
Cu N4 2.045(3) . ?
Cu N3 2.072(3) . ?
Cu C1 2.295(3) 2_666 ?
Cu Cu 2.3719(8) 2_666 ?
Cl1 C22 1.811(7) . ?
Cl2 C22 1.690(6) . ?
N1 C1 1.347(4) 2_666 ?
N1 C2 1.383(4) . ?
N1 C4 1.461(4) . ?
N2 C1 1.369(4) . ?
N2 C3 1.384(4) . ?
N2 C13 1.432(4) . ?
N3 C9 1.340(4) . ?
N3 C5 1.341(5) . ?
N4 N5 1.182(4) . ?
N5 N6 1.161(4) . ?
C2 C3 1.338(5) 2_666 ?
C2 H2 0.9500 . ?
C3 H3 0.9500 . ?
C4 C5 1.511(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.387(5) . ?
C6 C7 1.399(5) . ?
C6 C10 1.493(6) . ?
C7 C8 1.381(6) . ?
C7 O1B 1.384(6) . ?
C7 O1A 1.462(13) . ?
C8 C9 1.374(5) . ?
C8 C11 1.510(5) . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C13 C18 1.386(5) . ?
C13 C14 1.401(4) . ?
C14 C15 1.392(5) . ?
C14 C20 1.494(5) . ?
C15 C16 1.385(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(5) . ?
C16 C21 1.498(5) . ?
C17 C18 1.387(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.509(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O1A C12A 1.40(2) . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
O1B C12B 1.420(10) . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 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
C1 Cu N4 102.87(13) . . ?
C1 Cu N3 127.94(12) . . ?
N4 Cu N3 99.69(13) . . ?
C1 Cu C1 113.82(9) . 2_666 ?
N4 Cu C1 122.47(12) . 2_666 ?
N3 Cu C1 91.22(11) . 2_666 ?
C1 Cu Cu 62.29(9) . 2_666 ?
N4 Cu Cu 135.26(11) . 2_666 ?
N3 Cu Cu 123.15(8) . 2_666 ?
C1 Cu Cu 51.53(8) 2_666 2_666 ?
C1 N1 C2 112.2(3) 2_666 . ?
C1 N1 C4 123.8(3) 2_666 . ?
C2 N1 C4 124.0(3) . . ?
C1 N2 C3 111.4(3) . . ?
C1 N2 C13 123.7(2) . . ?
C3 N2 C13 124.4(2) . . ?
C9 N3 C5 118.1(3) . . ?
C9 N3 Cu 117.7(2) . . ?
C5 N3 Cu 123.4(2) . . ?
N5 N4 Cu 126.2(2) . . ?
N6 N5 N4 178.9(4) . . ?
N1 C1 N2 103.3(2) 2_666 . ?
N1 C1 Cu 123.0(2) 2_666 . ?
N2 C1 Cu 125.3(2) . . ?
N1 C1 Cu 106.31(19) 2_666 2_666 ?
N2 C1 Cu 129.7(2) . 2_666 ?
Cu C1 Cu 66.18(9) . 2_666 ?
C3 C2 N1 106.6(3) 2_666 . ?
C3 C2 H2 126.7 2_666 . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 106.6(3) 2_666 . ?
C2 C3 H3 126.7 2_666 . ?
N2 C3 H3 126.7 . . ?
N1 C4 C5 112.1(3) . . ?
N1 C4 H4A 109.2 . . ?
C5 C4 H4A 109.2 . . ?
N1 C4 H4B 109.2 . . ?
C5 C4 H4B 109.2 . . ?
H4A C4 H4B 107.9 . . ?
N3 C5 C6 123.1(3) . . ?
N3 C5 C4 115.5(3) . . ?
C6 C5 C4 121.4(3) . . ?
C5 C6 C7 116.3(4) . . ?
C5 C6 C10 122.7(3) . . ?
C7 C6 C10 121.1(3) . . ?
C8 C7 O1B 119.5(4) . . ?
C8 C7 C6 121.9(3) . . ?
O1B C7 C6 117.9(4) . . ?
C8 C7 O1A 120.4(6) . . ?
C6 C7 O1A 112.7(6) . . ?
C9 C8 C7 116.3(3) . . ?
C9 C8 C11 120.5(4) . . ?
C7 C8 C11 123.2(4) . . ?
N3 C9 C8 124.2(4) . . ?
N3 C9 H9 117.9 . . ?
C8 C9 H9 117.9 . . ?
C6 C10 H10A 109.5 . . ?
C6 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C6 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C18 C13 C14 122.4(3) . . ?
C18 C13 N2 119.9(3) . . ?
C14 C13 N2 117.7(3) . . ?
C15 C14 C13 117.4(3) . . ?
C15 C14 C20 120.7(3) . . ?
C13 C14 C20 121.9(3) . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?
C15 C16 C17 118.5(3) . . ?
C15 C16 C21 119.8(3) . . ?
C17 C16 C21 121.7(3) . . ?
C18 C17 C16 122.0(3) . . ?
C18 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
C13 C18 C17 117.7(3) . . ?
C13 C18 C19 121.2(3) . . ?
C17 C18 C19 121.1(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C14 C20 H20A 109.5 . . ?
C14 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C14 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl2 C22 Cl1 110.7(3) . . ?
Cl2 C22 H22A 109.5 . . ?
Cl1 C22 H22A 109.5 . . ?
Cl2 C22 H22B 109.5 . . ?
Cl1 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C12A O1A C7 106.2(15) . . ?
O1A C12A H12A 109.5 . . ?
O1A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
O1A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C7 O1B C12B 113.1(6) . . ?
O1B C12B H12D 109.5 . . ?
O1B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
O1B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 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
C3 N2 C1 N1 -0.1(3) . . . 2_666 ?
C13 N2 C1 N1 172.4(3) . . . 2_666 ?
C3 N2 C1 Cu -148.5(2) . . . . ?
C13 N2 C1 Cu 24.0(4) . . . . ?
C3 N2 C1 Cu 124.7(3) . . . 2_666 ?
C13 N2 C1 Cu -62.8(4) . . . 2_666 ?
C1 N1 C2 C3 0.8(4) 2_666 . . 2_666 ?
C4 N1 C2 C3 178.0(3) . . . 2_666 ?
C1 N2 C3 C2 -0.4(4) . . . 2_666 ?
C13 N2 C3 C2 -172.8(3) . . . 2_666 ?
C1 N1 C4 C5 85.2(4) 2_666 . . . ?
C2 N1 C4 C5 -91.7(4) . . . . ?
C9 N3 C5 C6 -2.2(5) . . . . ?
Cu N3 C5 C6 167.0(3) . . . . ?
C9 N3 C5 C4 179.5(3) . . . . ?
Cu N3 C5 C4 -11.3(4) . . . . ?
N1 C4 C5 N3 -49.7(4) . . . . ?
N1 C4 C5 C6 131.9(3) . . . . ?
N3 C5 C6 C7 -1.9(5) . . . . ?
C4 C5 C6 C7 176.4(3) . . . . ?
N3 C5 C6 C10 177.6(4) . . . . ?
C4 C5 C6 C10 -4.2(5) . . . . ?
C5 C6 C7 C8 4.8(6) . . . . ?
C10 C6 C7 C8 -174.7(4) . . . . ?
C5 C6 C7 O1B -165.6(4) . . . . ?
C10 C6 C7 O1B 14.9(7) . . . . ?
C5 C6 C7 O1A 159.7(8) . . . . ?
C10 C6 C7 O1A -19.8(9) . . . . ?
O1B C7 C8 C9 166.8(4) . . . . ?
C6 C7 C8 C9 -3.5(6) . . . . ?
O1A C7 C8 C9 -156.5(8) . . . . ?
O1B C7 C8 C11 -10.5(7) . . . . ?
C6 C7 C8 C11 179.3(4) . . . . ?
O1A C7 C8 C11 26.3(9) . . . . ?
C5 N3 C9 C8 3.7(5) . . . . ?
Cu N3 C9 C8 -166.1(3) . . . . ?
C7 C8 C9 N3 -1.0(6) . . . . ?
C11 C8 C9 N3 176.4(4) . . . . ?
C1 N2 C13 C18 94.1(4) . . . . ?
C3 N2 C13 C18 -94.4(4) . . . . ?
C1 N2 C13 C14 -86.4(4) . . . . ?
C3 N2 C13 C14 85.1(4) . . . . ?
C18 C13 C14 C15 -4.6(4) . . . . ?
N2 C13 C14 C15 175.8(3) . . . . ?
C18 C13 C14 C20 173.5(3) . . . . ?
N2 C13 C14 C20 -6.0(4) . . . . ?
C13 C14 C15 C16 1.9(5) . . . . ?
C20 C14 C15 C16 -176.2(3) . . . . ?
C14 C15 C16 C17 1.1(5) . . . . ?
C14 C15 C16 C21 178.7(3) . . . . ?
C15 C16 C17 C18 -1.8(5) . . . . ?
C21 C16 C17 C18 -179.3(3) . . . . ?
C14 C13 C18 C17 4.1(4) . . . . ?
N2 C13 C18 C17 -176.4(3) . . . . ?
C14 C13 C18 C19 -174.2(3) . . . . ?
N2 C13 C18 C19 5.3(4) . . . . ?
C16 C17 C18 C13 -0.8(4) . . . . ?
C16 C17 C18 C19 177.5(3) . . . . ?
C8 C7 O1A C12A -80(2) . . . . ?
C6 C7 O1A C12A 124.8(18) . . . . ?
C8 C7 O1B C12B 83.6(8) . . . . ?
C6 C7 O1B C12B -105.8(6) . . . . ?

_refine_diff_density_max         2.054
_refine_diff_density_min         -1.243
_refine_diff_density_rms         0.094

####################################################################### 
# 
# 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_P21n_CXautre_a
_database_code_depnum_ccdc_archive 'CCDC 2284249'
loop_
_audit_author_name
_audit_author_address
'Laurent Jouffret'
;Institut de Chimie de Clermont Ferrand, CNRS, Universite Clermont Auvergne, France
France
;
_audit_update_record             
;
2023-08-29 deposited with the CCDC.	2023-09-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_formula_sum            'C21 H25 Cl Cu N3 O'
_chemical_formula_weight         434.43

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

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

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

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

_cell_length_a                   14.3299(15)
_cell_length_b                   9.6126(10)
_cell_length_c                   14.9035(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.387(4)
_cell_angle_gamma                90
_cell_volume                     2052.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12734
_cell_measurement_theta_min      1.3823
_cell_measurement_theta_max      30.8430
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.504
_exptl_crystal_size_mid          0.239
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    1.209
_shelx_estimated_absorpt_T_min   0.581
_shelx_estimated_absorpt_T_max   0.878
_exptl_absorpt_correction_type   'Numerical Mu From Formula'
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_T_max  0.88
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   molybdene
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            168008
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         30.507
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6281
_reflns_number_gt                5179
_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       APEX2
_computing_cell_refinement       'APEX3 v2019.11-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 994)'
_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)+(0.0286P)²+2.2658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6281
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0311
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0722
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
Cu Cu 0.36603(2) 0.45164(2) 0.32536(2) 0.01109(5) Uani 1 1 d . . . . .
Cl Cl 0.33932(3) 0.51458(5) 0.46555(3) 0.02172(9) Uani 1 1 d . . . . .
O1 O -0.08223(8) 0.38977(12) 0.15925(8) 0.0173(2) Uani 1 1 d . . . . .
N1 N 0.27421(8) 0.61628(13) 0.18210(9) 0.0109(2) Uani 1 1 d . . . . .
N2 N 0.39662(9) 0.51384(14) 0.13425(9) 0.0126(2) Uani 1 1 d . . . . .
N3 N 0.06715(9) 0.75909(13) 0.16249(9) 0.0111(2) Uani 1 1 d . . . . .
C1 C 0.34272(10) 0.52739(15) 0.20896(10) 0.0108(3) Uani 1 1 d . . . . .
C2 C 0.28584(11) 0.65925(17) 0.09398(11) 0.0150(3) Uani 1 1 d . . . . .
H2 H 0.247233 0.722136 0.061476 0.018 Uiso 1 1 calc R U . . .
C3 C 0.36294(11) 0.59395(18) 0.06352(11) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.388953 0.601370 0.005258 0.020 Uiso 1 1 calc R U . . .
C4 C 0.19865(10) 0.66071(16) 0.24129(10) 0.0117(3) Uani 1 1 d . . . . .
H4A H 0.207676 0.759881 0.257039 0.014 Uiso 1 1 calc R U . . .
H4B H 0.201563 0.605967 0.297508 0.014 Uiso 1 1 calc R U . . .
C5 C 0.10343(10) 0.64249(16) 0.19859(10) 0.0109(3) Uani 1 1 d . . . . .
C6 C 0.05727(11) 0.51469(16) 0.19736(11) 0.0134(3) Uani 1 1 d . . . . .
C7 C -0.03130(11) 0.51115(17) 0.15742(11) 0.0128(3) Uani 1 1 d . . . . .
C8 C -0.07048(11) 0.63052(17) 0.12030(11) 0.0151(3) Uani 1 1 d . . . . .
C9 C -0.01788(11) 0.75161(17) 0.12398(11) 0.0145(3) Uani 1 1 d . . . . .
H9 H -0.043271 0.833606 0.097921 0.017 Uiso 1 1 calc R U . . .
C10 C 0.09863(13) 0.38519(18) 0.23810(14) 0.0242(4) Uani 1 1 d . . . . .
H10A H 0.050496 0.335471 0.271755 0.036 Uiso 1 1 calc R U . . .
H10B H 0.149892 0.410746 0.278712 0.036 Uiso 1 1 calc R U . . .
H10C H 0.122424 0.325016 0.190356 0.036 Uiso 1 1 calc R U . . .
C11 C -0.16599(12) 0.6308(2) 0.07800(14) 0.0259(4) Uani 1 1 d . . . . .
H11A H -0.183542 0.726266 0.062255 0.039 Uiso 1 1 calc R U . . .
H11B H -0.211264 0.592835 0.120499 0.039 Uiso 1 1 calc R U . . .
H11C H -0.165451 0.573328 0.023679 0.039 Uiso 1 1 calc R U . . .
C12 C -0.06891(14) 0.3046(2) 0.08066(13) 0.0253(4) Uani 1 1 d . . . . .
H12A H -0.111788 0.225289 0.082422 0.038 Uiso 1 1 calc R U . . .
H12B H -0.004423 0.270769 0.079463 0.038 Uiso 1 1 calc R U . . .
H12C H -0.081450 0.360040 0.026712 0.038 Uiso 1 1 calc R U . . .
C13 C 0.47106(10) 0.41300(17) 0.12997(10) 0.0131(3) Uani 1 1 d . . . . .
C14 C 0.45383(11) 0.28640(18) 0.08731(11) 0.0154(3) Uani 1 1 d . . . . .
C15 C 0.52229(12) 0.18402(19) 0.09316(12) 0.0194(3) Uani 1 1 d . . . . .
H15 H 0.511352 0.096557 0.065336 0.023 Uiso 1 1 calc R U . . .
C16 C 0.60621(12) 0.2058(2) 0.13846(11) 0.0220(4) Uani 1 1 d . . . . .
C17 C 0.62211(12) 0.3353(2) 0.17673(12) 0.0225(4) Uani 1 1 d . . . . .
H17 H 0.680195 0.352513 0.205750 0.027 Uiso 1 1 calc R U . . .
C18 C 0.55542(11) 0.44108(19) 0.17393(11) 0.0178(3) Uani 1 1 d . . . . .
C19 C 0.57280(13) 0.5779(2) 0.21949(15) 0.0285(4) Uani 1 1 d . . . . .
H19A H 0.552373 0.653818 0.180078 0.043 Uiso 1 1 calc R U . . .
H19B H 0.639613 0.587834 0.232445 0.043 Uiso 1 1 calc R U . . .
H19C H 0.537784 0.581535 0.275692 0.043 Uiso 1 1 calc R U . . .
C20 C 0.36410(12) 0.2597(2) 0.03708(12) 0.0219(3) Uani 1 1 d . . . . .
H20A H 0.311544 0.295398 0.071967 0.033 Uiso 1 1 calc R U . . .
H20B H 0.356390 0.159461 0.027718 0.033 Uiso 1 1 calc R U . . .
H20C H 0.365953 0.306962 -0.021157 0.033 Uiso 1 1 calc R U . . .
C21 C 0.67719(16) 0.0905(3) 0.14641(14) 0.0349(5) Uani 1 1 d . . . . .
H21A H 0.647280 0.007158 0.170924 0.052 Uiso 1 1 calc R U . . .
H21B H 0.727967 0.119875 0.186488 0.052 Uiso 1 1 calc R U . . .
H21C H 0.702423 0.069425 0.086982 0.052 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
Cu C1 1.9087(15) . ?
Cu N3 2.0913(13) 2_545 ?
Cu Cl 2.2111(5) . ?
O1 C7 1.3766(18) . ?
O1 C12 1.442(2) . ?
N1 C1 1.3598(19) . ?
N1 C2 1.388(2) . ?
N1 C4 1.4649(19) . ?
N2 C1 1.366(2) . ?
N2 C3 1.389(2) . ?
N2 C13 1.4430(19) . ?
N3 C9 1.3453(19) . ?
N3 C5 1.3462(19) . ?
C2 C3 1.352(2) . ?
C4 C5 1.512(2) . ?
C5 C6 1.395(2) . ?
C6 C7 1.399(2) . ?
C6 C10 1.505(2) . ?
C7 C8 1.391(2) . ?
C8 C9 1.388(2) . ?
C8 C11 1.503(2) . ?
C13 C14 1.394(2) . ?
C13 C18 1.397(2) . ?
C14 C15 1.392(2) . ?
C14 C20 1.506(2) . ?
C15 C16 1.391(3) . ?
C16 C17 1.388(3) . ?
C16 C21 1.508(3) . ?
C17 C18 1.396(2) . ?
C18 C19 1.500(3) . ?

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
C1 Cu N3 119.58(6) . 2_545 ?
C1 Cu Cl 136.39(5) . . ?
N3 Cu Cl 104.03(4) 2_545 . ?
C7 O1 C12 113.06(13) . . ?
C1 N1 C2 112.00(13) . . ?
C1 N1 C4 122.75(13) . . ?
C2 N1 C4 125.25(13) . . ?
C1 N2 C3 111.73(13) . . ?
C1 N2 C13 121.50(13) . . ?
C3 N2 C13 126.29(13) . . ?
C9 N3 C5 118.19(13) . . ?
C9 N3 Cu 119.81(10) . 2 ?
C5 N3 Cu 121.79(10) . 2 ?
N1 C1 N2 103.36(13) . . ?
N1 C1 Cu 128.97(11) . . ?
N2 C1 Cu 127.46(11) . . ?
C3 C2 N1 106.45(14) . . ?
C2 C3 N2 106.45(14) . . ?
N1 C4 C5 112.41(12) . . ?
N3 C5 C6 123.09(14) . . ?
N3 C5 C4 114.64(13) . . ?
C6 C5 C4 122.27(14) . . ?
C5 C6 C7 117.11(14) . . ?
C5 C6 C10 122.53(14) . . ?
C7 C6 C10 120.35(14) . . ?
O1 C7 C8 119.64(14) . . ?
O1 C7 C6 119.47(14) . . ?
C8 C7 C6 120.80(14) . . ?
C9 C8 C7 117.31(14) . . ?
C9 C8 C11 120.54(15) . . ?
C7 C8 C11 122.15(15) . . ?
N3 C9 C8 123.49(15) . . ?
C14 C13 C18 122.16(15) . . ?
C14 C13 N2 118.53(14) . . ?
C18 C13 N2 119.14(15) . . ?
C15 C14 C13 117.78(15) . . ?
C15 C14 C20 120.66(16) . . ?
C13 C14 C20 121.56(15) . . ?
C16 C15 C14 122.06(17) . . ?
C17 C16 C15 118.24(16) . . ?
C17 C16 C21 121.22(18) . . ?
C15 C16 C21 120.53(19) . . ?
C16 C17 C18 122.07(16) . . ?
C17 C18 C13 117.60(16) . . ?
C17 C18 C19 120.90(16) . . ?
C13 C18 C19 121.47(15) . . ?

_refine_diff_density_max         0.508
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.075

