# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_cu_t_2022_11_2_273k_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2219275'
loop_
_audit_author_name
_audit_author_address
terigele
;Zhejiang Normal University
China
;
_audit_update_record             
;
2023-03-13 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Cl8 Cu2), 2(C8 H12 N O)'
_chemical_formula_sum            'C16 H24 Cl4 Cu N2 O2'
_chemical_formula_weight         481.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z'
'x+1/2, -y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z'
'-x-1/2, y-1/2, z-1/2'

_cell_length_a                   10.504(3)
_cell_length_b                   36.811(14)
_cell_length_c                   5.2766(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2040.3(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2063
_cell_measurement_temperature    273.00
_cell_measurement_theta_max      68.1665
_cell_measurement_theta_min      2.4015
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.438
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1150 before and 0.0640 after correction.
The Ratio of minimum to maximum transmission is 0.7723.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             988
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1119
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            20668
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.488
_diffrn_reflns_theta_min         2.401
_diffrn_ambient_temperature      273.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1049
_reflns_number_total             1891
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.790
_refine_diff_density_min         -0.861
_refine_diff_density_rms         0.083
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     152
_refine_ls_number_reflns         1891
_refine_ls_number_restraints     171
_refine_ls_R_factor_all          0.1103
_refine_ls_R_factor_gt           0.0670
_refine_ls_restrained_S_all      1.660
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0736P)²+3.8885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1635
_refine_ls_wR_factor_ref         0.1886
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C9-C6
 3 with sigma of 0.02
 O1-C5 \\sim O2-C5 \\sim O2-C9 \\sim O1-C8
 with sigma of 0.02
 Cu1-Cl5 \\sim Cu1-Cl4
 with sigma of 0.02
 Cu1-Cl2 \\sim Cu1-Cl3
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6
\\sim C7 \\sim C8 \\sim C9: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Cu1 \\sim Cl1 \\sim Cl4 \\sim Cl5: within 4A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(Cl5) \\sim Ueq, Uanis(Cl4) \\sim Ueq, Uanis(Cl2) \\sim Ueq, Uanis(Cl3)
\\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Sof(O2)=Sof(C9)=Sof(H9A)=Sof(H9B)=Sof(H9C)=1-FVAR(1)
 Sof(O1)=Sof(C8)=Sof(H8A)=Sof(H8B)=Sof(H8C)=FVAR(1)
 Fixed Sof: Cl2(0.25) Cl3(0.25) Cl4(0.25) Cl5(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C1(H1D,H1E)
5.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7)
5.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.68118(9) 0.750000 0.2400(2) 0.0534(4) Uani 1 2 d DS TU P . .
Cl1 Cl 0.66906(16) 0.68828(5) 0.2382(3) 0.0729(5) Uani 1 1 d . U . . .
Cl2 Cl 0.6991(5) 0.750000 -0.1940(9) 0.0634(15) Uani 0.5 2 d DS TU P A .
Cl3 Cl 0.6943(5) 0.750000 -0.3204(9) 0.0617(14) Uani 0.5 2 d DS TU P A .
Cl4 Cl 0.8942(4) 0.750000 0.2646(9) 0.0564(11) Uani 0.5 2 d DS TU P A 1
Cl5 Cl 0.9573(5) 0.750000 0.2689(10) 0.0777(14) Uani 0.5 2 d DS TU P A 2
O1 O 0.569(3) 0.5363(7) 0.286(5) 0.112(3) Uani 0.204(11) 1 d D U . B 1
O2 O 0.6619(9) 0.5385(2) 0.3923(17) 0.120(3) Uani 0.796(11) 1 d D U . B 2
N1 N 0.4503(6) 0.69403(17) 0.7271(10) 0.0769(16) Uani 1 1 d . U . . .
H1A H 0.449246 0.697779 0.560452 0.092 Uiso 1 1 calc GR . . . .
H1B H 0.530339 0.694550 0.782481 0.092 Uiso 1 1 calc GR . . . .
H1C H 0.405582 0.711339 0.804092 0.092 Uiso 1 1 calc GR . . . .
C1 C 0.3951(7) 0.6592(2) 0.7823(14) 0.083(2) Uani 1 1 d . U . . .
H1D H 0.307020 0.659346 0.727165 0.100 Uiso 1 1 calc R . . . .
H1E H 0.395359 0.655682 0.964541 0.100 Uiso 1 1 calc R . . . .
C2 C 0.4608(7) 0.6274(2) 0.6617(12) 0.0702(17) Uani 1 1 d . U . . .
C3 C 0.5712(8) 0.6149(2) 0.7640(15) 0.0856(19) Uani 1 1 d . U . . .
H3 H 0.605204 0.626649 0.904455 0.103 Uiso 1 1 calc R . . . .
C4 C 0.6337(10) 0.5855(3) 0.6663(18) 0.106(2) Uani 1 1 d . U . . .
H4 H 0.710339 0.577575 0.735437 0.127 Uiso 1 1 calc R . . . .
C5 C 0.5803(10) 0.5680(2) 0.4642(19) 0.103(2) Uani 1 1 d D U . . .
C6 C 0.4670(10) 0.5805(2) 0.3561(16) 0.099(2) Uani 1 1 d D U . . .
H6 H 0.431209 0.568517 0.218130 0.119 Uiso 1 1 calc R . . . .
C7 C 0.4098(8) 0.6104(2) 0.4560(14) 0.088(2) Uani 1 1 d . U . . .
H7 H 0.335400 0.619330 0.383358 0.105 Uiso 1 1 calc R . . . .
C8 C 0.681(4) 0.5121(13) 0.285(10) 0.120(7) Uani 0.204(11) 1 d D U . B 1
H8A H 0.657157 0.489035 0.214361 0.180 Uiso 0.204(11) 1 calc GR . . B 1
H8B H 0.709916 0.508736 0.455913 0.180 Uiso 0.204(11) 1 calc GR . . B 1
H8C H 0.747164 0.522750 0.185336 0.180 Uiso 0.204(11) 1 calc GR . . B 1
C9 C 0.6011(15) 0.5163(4) 0.193(3) 0.134(5) Uani 0.796(11) 1 d D U . B 2
H9A H 0.569081 0.531913 0.062178 0.202 Uiso 0.796(11) 1 calc GR . . B 2
H9B H 0.532143 0.502718 0.265594 0.202 Uiso 0.796(11) 1 calc GR . . B 2
H9C H 0.662671 0.499902 0.122891 0.202 Uiso 0.796(11) 1 calc GR . . B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl1 2.276(2) . ?
Cu1 Cl1 2.276(2) 7_575 ?
Cu1 Cl2 2.298(5) . ?
Cu1 Cl3 2.324(5) 1_556 ?
Cu1 Cl3 2.960(5) . ?
Cu1 Cl4 2.241(4) . ?
Cu1 Cl5 2.352(6) 6_556 ?
Cu1 Cl5 2.904(6) . ?
Cl2 Cl3 0.669(4) . ?
O1 C5 1.505(17) . ?
O1 C8 1.467(18) . ?
O2 C5 1.432(11) . ?
O2 C9 1.476(12) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.439(10) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C1 C2 1.498(11) . ?
C2 C3 1.361(10) . ?
C2 C7 1.363(10) . ?
C3 H3 0.9300 . ?
C3 C4 1.368(12) . ?
C4 H4 0.9300 . ?
C4 C5 1.366(12) . ?
C5 C6 1.398(13) . ?
C6 H6 0.9300 . ?
C6 C7 1.362(11) . ?
C7 H7 0.9300 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl1 173.57(10) . 7_575 ?
Cl1 Cu1 Cl2 90.02(6) . . ?
Cl1 Cu1 Cl2 90.02(6) 7_575 . ?
Cl1 Cu1 Cl3 90.44(6) . 1_556 ?
Cl1 Cu1 Cl3 90.44(5) 7_575 1_556 ?
Cl1 Cu1 Cl3 89.90(6) 7_575 . ?
Cl1 Cu1 Cl3 89.90(6) . . ?
Cl1 Cu1 Cl5 93.21(5) 7_575 . ?
Cl1 Cu1 Cl5 86.79(5) . 6_556 ?
Cl1 Cu1 Cl5 93.21(5) . . ?
Cl1 Cu1 Cl5 86.79(5) 7_575 6_556 ?
Cl2 Cu1 Cl3 171.90(14) . 1_556 ?
Cl2 Cu1 Cl3 2.0(2) . . ?
Cl2 Cu1 Cl5 93.6(2) . 6_556 ?
Cl2 Cu1 Cl5 88.30(19) . . ?
Cl3 Cu1 Cl3 173.9(3) 1_556 . ?
Cl3 Cu1 Cl5 94.5(2) 1_556 6_556 ?
Cl3 Cu1 Cl5 83.60(18) 1_556 . ?
Cl4 Cu1 Cl1 93.21(5) . 7_575 ?
Cl4 Cu1 Cl1 93.21(5) . . ?
Cl4 Cu1 Cl2 88.62(18) . . ?
Cl4 Cu1 Cl3 90.65(17) . . ?
Cl4 Cu1 Cl3 83.28(17) . 1_556 ?
Cl4 Cu1 Cl5 177.8(2) . 6_556 ?
Cl5 Cu1 Cl3 90.33(15) . . ?
Cl5 Cu1 Cl3 91.52(17) 6_556 . ?
Cl5 Cu1 Cl5 178.14(5) 6_556 . ?
Cl3 Cl2 Cu1 171.0(10) . . ?
Cu1 Cl3 Cu1 173.9(2) 1_554 . ?
Cl2 Cl3 Cu1 7.0(7) . . ?
Cl2 Cl3 Cu1 179.1(10) . 1_554 ?
Cu1 Cl5 Cu1 175.9(2) 6_656 . ?
C8 O1 C5 114(3) . . ?
C5 O2 C9 110.4(10) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
N1 C1 H1D 108.5 . . ?
N1 C1 H1E 108.5 . . ?
N1 C1 C2 115.1(6) . . ?
H1D C1 H1E 107.5 . . ?
C2 C1 H1D 108.5 . . ?
C2 C1 H1E 108.5 . . ?
C3 C2 C1 119.3(7) . . ?
C3 C2 C7 119.6(8) . . ?
C7 C2 C1 121.1(8) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(8) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 118.1(10) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 O1 152.4(17) . . ?
C4 C5 O2 108.5(10) . . ?
C4 C5 C6 120.9(9) . . ?
C6 C5 O1 86.2(15) . . ?
C6 C5 O2 130.5(9) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 C5 119.0(9) . . ?
C7 C6 H6 120.5 . . ?
C2 C7 H7 119.8 . . ?
C6 C7 C2 120.5(9) . . ?
C6 C7 H7 119.8 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
O1 C5 C6 C7 174.1(15) . . . . ?
O2 C5 C6 C7 -177.2(9) . . . . ?
N1 C1 C2 C3 77.8(9) . . . . ?
N1 C1 C2 C7 -104.1(8) . . . . ?
C1 C2 C3 C4 178.3(8) . . . . ?
C1 C2 C7 C6 -176.6(7) . . . . ?
C2 C3 C4 C5 -1.8(13) . . . . ?
C3 C2 C7 C6 1.5(12) . . . . ?
C3 C4 C5 O1 -166(3) . . . . ?
C3 C4 C5 O2 179.4(8) . . . . ?
C3 C4 C5 C6 1.8(14) . . . . ?
C4 C5 C6 C7 -0.2(14) . . . . ?
C5 C6 C7 C2 -1.5(13) . . . . ?
C7 C2 C3 C4 0.1(12) . . . . ?
C8 O1 C5 C4 -18(5) . . . . ?
C8 O1 C5 C6 173(3) . . . . ?
C9 O2 C5 C4 173.6(9) . . . . ?
C9 O2 C5 C6 -9.2(16) . . . . ?

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

data_123
_database_code_depnum_ccdc_archive 'CCDC 2219277'
loop_
_audit_author_name
_audit_author_address
terigele
;Zhejiang Normal University
China
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-02-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Cu, 2(C7 H10 N)'
_chemical_formula_sum            'C14 H20 Cl4 Cu N2'
_chemical_formula_weight         421.66
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   31.706(5)
_cell_length_b                   5.2429(7)
_cell_length_c                   10.5574(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.116(6)
_cell_angle_gamma                90
_cell_volume                     1737.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4686
_cell_measurement_temperature    300.0
_cell_measurement_theta_max      28.392
_cell_measurement_theta_min      2.595
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.866
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.5996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1197 before and 0.0686 after correction.
The Ratio of minimum to maximum transmission is 0.8032.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             860
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_av_unetI/netI     0.0613
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            17316
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.270
_diffrn_reflns_theta_min         2.596
_diffrn_ambient_temperature      300.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    0.961
_reflns_Friedel_fraction_max     0.906
_reflns_number_gt                2955
_reflns_number_total             4076
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.699
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4076
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.1018
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.00(2)
 0.00(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
3. Others
 Sof(Cl2)=1-FVAR(1)
 Sof(Cl0A)=FVAR(1)
 Sof(Cl1A)=1-FVAR(2)
 Sof(Cl1)=FVAR(2)
4.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C1(H1D,H1E)
4.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C10(H10), C3(H3), C7(H7), C13(H13), C11(H11), C6(H6), C4(H4),
 C5(H5), C12(H12)
4.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49375(3) 0.01124(10) 0.43158(8) 0.02951(17) Uani 1 1 d . . . . .
Cl3 Cl 0.42127(6) 0.0144(3) 0.39287(18) 0.0489(5) Uani 1 1 d . . . . .
Cl1 Cl 0.49401(14) -0.0152(5) 0.6474(12) 0.044(2) Uani 0.51(3) 1 d . . P A 1
Cl2 Cl 0.49375(15) 0.449(2) 0.4463(4) 0.0439(16) Uani 0.52(2) 1 d . . P A 2
Cl4 Cl 0.56635(5) 0.0146(3) 0.45272(18) 0.0503(5) Uani 1 1 d . . . . .
N2 N 0.4282(2) 0.4737(10) 0.6701(7) 0.0592(18) Uani 1 1 d . . . . .
H2A H 0.447195 0.580386 0.644816 0.071 Uiso 1 1 calc GR . . . .
H2B H 0.434819 0.314348 0.651492 0.071 Uiso 1 1 calc GR . . . .
H2C H 0.428402 0.488614 0.754116 0.071 Uiso 1 1 calc GR . . . .
N1 N 0.55934(19) 0.4780(9) 0.7268(7) 0.0535(17) Uani 1 1 d . . . . .
H1A H 0.539635 0.575554 0.682064 0.064 Uiso 1 1 calc GR . . . .
H1B H 0.559180 0.504264 0.810020 0.064 Uiso 1 1 calc GR . . . .
H1C H 0.553695 0.314701 0.708582 0.064 Uiso 1 1 calc GR . . . .
C14 C 0.3321(2) 0.1817(11) 0.5906(6) 0.0470(14) Uani 1 1 d . . . . .
H14 H 0.341542 0.126895 0.515729 0.056 Uiso 1 1 calc R . . . .
C8 C 0.3862(2) 0.5351(12) 0.6046(7) 0.0578(18) Uani 1 1 d . . . . .
H8A H 0.385253 0.498164 0.514177 0.069 Uiso 1 1 calc R . . . .
H8B H 0.381245 0.716512 0.613059 0.069 Uiso 1 1 calc R . . . .
C10 C 0.3360(2) 0.4748(11) 0.7643(6) 0.0488(14) Uani 1 1 d . . . . .
H10 H 0.347694 0.619076 0.807026 0.059 Uiso 1 1 calc R . . . .
C9 C 0.35099(18) 0.3913(11) 0.6543(5) 0.0391(12) Uani 1 1 d . . . . .
C3 C 0.6558(2) 0.1973(11) 0.7273(6) 0.0497(14) Uani 1 1 d . . . . .
H3 H 0.645623 0.133786 0.646458 0.060 Uiso 1 1 calc R . . . .
C2 C 0.63694(19) 0.4048(11) 0.7726(5) 0.0408(12) Uani 1 1 d . . . . .
C7 C 0.6523(2) 0.4955(11) 0.8939(7) 0.0532(16) Uani 1 1 d . . . . .
H7 H 0.639735 0.637261 0.926282 0.064 Uiso 1 1 calc R . . . .
C13 C 0.2998(2) 0.0534(12) 0.6351(7) 0.0565(17) Uani 1 1 d . . . . .
H13 H 0.287496 -0.088250 0.591394 0.068 Uiso 1 1 calc R . . . .
C11 C 0.3036(2) 0.3416(15) 0.8102(7) 0.0612(17) Uani 1 1 d . . . . .
H11 H 0.294252 0.393786 0.885721 0.073 Uiso 1 1 calc R . . . .
C6 C 0.6858(2) 0.3763(16) 0.9658(7) 0.0648(18) Uani 1 1 d . . . . .
H6 H 0.696139 0.438830 1.046722 0.078 Uiso 1 1 calc R . . . .
C4 C 0.6899(2) 0.0805(13) 0.8006(7) 0.0615(18) Uani 1 1 d . . . . .
H4 H 0.703007 -0.058372 0.767776 0.074 Uiso 1 1 calc R . . . .
C1 C 0.6010(2) 0.5423(13) 0.6937(7) 0.0585(19) Uani 1 1 d . . . . .
H1D H 0.605492 0.724529 0.704406 0.070 Uiso 1 1 calc R . . . .
H1E H 0.601500 0.502310 0.604239 0.070 Uiso 1 1 calc R . . . .
C5 C 0.7044(2) 0.1663(16) 0.9202(7) 0.0675(19) Uani 1 1 d . . . . .
H5 H 0.726672 0.083227 0.970514 0.081 Uiso 1 1 calc R . . . .
C12 C 0.2854(2) 0.1365(15) 0.7465(7) 0.0621(18) Uani 1 1 d . . . . .
H12 H 0.263211 0.051080 0.777338 0.075 Uiso 1 1 calc R . . . .
Cl0A Cl 0.49365(17) 0.576(2) 0.4441(4) 0.0408(15) Uani 0.48(2) 1 d . . P A 1
Cl1A Cl 0.49314(15) -0.0180(6) 0.7124(12) 0.047(2) Uani 0.49(3) 1 d . . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl3 2.2766(19) . ?
Cu1 Cl1 2.281(13) . ?
Cu1 Cl2 2.299(12) . ?
Cu1 Cl4 2.281(2) . ?
Cu1 Cl0A 2.288(12) 1_545 ?
Cu1 Cl1A 2.312(13) 2_554 ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C8 1.448(9) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.454(10) . ?
C14 H14 0.9300 . ?
C14 C9 1.380(8) . ?
C14 C13 1.363(9) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.501(8) . ?
C10 H10 0.9300 . ?
C10 C9 1.386(9) . ?
C10 C11 1.386(9) . ?
C3 H3 0.9300 . ?
C3 C2 1.360(8) . ?
C3 C4 1.381(9) . ?
C2 C7 1.388(9) . ?
C2 C1 1.497(8) . ?
C7 H7 0.9300 . ?
C7 C6 1.368(9) . ?
C13 H13 0.9300 . ?
C13 C12 1.391(10) . ?
C11 H11 0.9300 . ?
C11 C12 1.354(10) . ?
C6 H6 0.9300 . ?
C6 C5 1.368(10) . ?
C4 H4 0.9300 . ?
C4 C5 1.358(10) . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C5 H5 0.9300 . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl3 Cu1 Cl1 92.35(13) . . ?
Cl3 Cu1 Cl2 89.73(13) . . ?
Cl3 Cu1 Cl4 175.24(9) . . ?
Cl3 Cu1 Cl0A 90.46(14) . 1_545 ?
Cl3 Cu1 Cl1A 87.40(13) . 2_554 ?
Cl1 Cu1 Cl4 92.37(13) . . ?
Cl1 Cu1 Cl0A 83.21(13) . 1_545 ?
Cl1 Cu1 Cl1A 177.38(12) . 2_554 ?
Cl2 Cu1 Cl1A 92.99(14) . 2_554 ?
Cl4 Cu1 Cl2 89.72(13) . . ?
Cl4 Cu1 Cl0A 90.67(14) . 1_545 ?
Cl4 Cu1 Cl1A 87.91(13) . 2_554 ?
Cl0A Cu1 Cl1A 94.18(14) 1_545 2_554 ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C8 N2 H2A 109.5 . . ?
C8 N2 H2B 109.5 . . ?
C8 N2 H2C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C13 C14 C9 121.4(6) . . ?
N2 C8 H8A 108.8 . . ?
N2 C8 H8B 108.8 . . ?
N2 C8 C9 113.6(5) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C11 C10 C9 119.5(6) . . ?
C14 C9 C8 121.6(6) . . ?
C14 C9 C10 118.9(5) . . ?
C10 C9 C8 119.5(6) . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.3(6) . . ?
C4 C3 H3 119.8 . . ?
C3 C2 C7 119.0(5) . . ?
C3 C2 C1 121.8(6) . . ?
C7 C2 C1 119.2(6) . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 119.9(6) . . ?
C6 C7 H7 120.0 . . ?
C14 C13 H13 120.4 . . ?
C14 C13 C12 119.3(6) . . ?
C12 C13 H13 120.4 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.8(6) . . ?
C12 C11 H11 119.6 . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.8(6) . . ?
C5 C6 H6 119.6 . . ?
C3 C4 H4 119.7 . . ?
C5 C4 C3 120.7(6) . . ?
C5 C4 H4 119.7 . . ?
N1 C1 C2 113.6(5) . . ?
N1 C1 H1D 108.8 . . ?
N1 C1 H1E 108.8 . . ?
C2 C1 H1D 108.8 . . ?
C2 C1 H1E 108.8 . . ?
H1D C1 H1E 107.7 . . ?
C6 C5 H5 120.4 . . ?
C4 C5 C6 119.2(6) . . ?
C4 C5 H5 120.4 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.1(6) . . ?
C11 C12 H12 120.0 . . ?

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
N2 C8 C9 C14 -101.3(7) . . . . ?
N2 C8 C9 C10 80.8(7) . . . . ?
C14 C13 C12 C11 -0.5(10) . . . . ?
C10 C11 C12 C13 1.4(10) . . . . ?
C9 C14 C13 C12 0.5(9) . . . . ?
C9 C10 C11 C12 -2.3(9) . . . . ?
C3 C2 C7 C6 0.0(10) . . . . ?
C3 C2 C1 N1 100.9(7) . . . . ?
C3 C4 C5 C6 -2.4(12) . . . . ?
C2 C3 C4 C5 1.8(11) . . . . ?
C2 C7 C6 C5 -0.6(11) . . . . ?
C7 C2 C1 N1 -81.0(8) . . . . ?
C7 C6 C5 C4 1.8(12) . . . . ?
C13 C14 C9 C8 -179.2(6) . . . . ?
C13 C14 C9 C10 -1.3(8) . . . . ?
C11 C10 C9 C14 2.2(8) . . . . ?
C11 C10 C9 C8 -179.9(5) . . . . ?
C4 C3 C2 C7 -0.6(9) . . . . ?
C4 C3 C2 C1 177.6(6) . . . . ?
C1 C2 C7 C6 -178.2(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.00(2)
2 0.00(2)

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

data_mo_te_2022_11_432k_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 2219276'
loop_
_audit_author_name
_audit_author_address
terigele
;Zhejiang Normal University
China
;
_audit_update_record             
;
2023-03-16 deposited with the CCDC.	2023-05-29 downloaded from the CCDC.
;
_audit_creation_date             2023-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(Cl8 Cu2), 2(C8 H12 N O)'
_chemical_formula_sum            'C16 H24 Cl4 Cu N2 O2'
_chemical_formula_weight         481.71
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   10.693(4)
_cell_length_b                   37.267(11)
_cell_length_c                   5.3299(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2123.9(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1396
_cell_measurement_temperature    432.15
_cell_measurement_theta_max      21.815
_cell_measurement_theta_min      2.196
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.543
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1390 before and 0.0793 after correction.
The Ratio of minimum to maximum transmission is 0.7727.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.506
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             988
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1927
_diffrn_reflns_av_unetI/netI     0.1102
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       44
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            21601
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         2.186
_diffrn_ambient_temperature      432.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                933
_reflns_number_total             1913
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.524
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       0.0048(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         1913
_refine_ls_number_restraints     316
_refine_ls_R_factor_all          0.1114
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1400
_refine_ls_wR_factor_ref         0.1690
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-C15 = O2-C16
 1.43 with sigma of 0.02
 O2-C1 = O1-C2
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O1 \\sim O2 \\sim N1 \\sim N2 \\sim C0 \\sim C1 \\sim C2 \\sim C5 \\sim C6
\\sim C7 \\sim C8 \\sim C9 \\sim C009 \\sim C10 \\sim C11 \\sim C12 \\sim C13
\\sim C14 \\sim C15 \\sim C16: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
4. Others
 Sof(O2)=Sof(N2)=Sof(H2D)=Sof(H2E)=Sof(H2F)=Sof(C0)=Sof(H0A)=Sof(H0B)=Sof(C1)=
 Sof(H1D)=Sof(H1E)=Sof(H1F)=Sof(C16)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=
 Sof(C9)=Sof(C8)=Sof(H8)=Sof(C6)=Sof(H6)=1-FVAR(1)
 Sof(O1)=Sof(N1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(H2C)=
 Sof(C009)=Sof(H00A)=Sof(H00B)=Sof(C15)=Sof(C13)=Sof(H13)=Sof(C11)=Sof(H11)=
 Sof(C10)=Sof(C7)=Sof(H7)=Sof(C5)=Sof(H5)=FVAR(1)
 Fixed Sof: Cl0A(0.25) Cl1A(0.25) Cl2(0.25) Cl3(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C0(H0A,H0B), C009(H00A,H00B)
5.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C11(H11), C7(H7), C5(H5), C14(H14), C12(H12), C8(H8), C6(H6)
5.c Fitted hexagon refined as free rotating group:
 C15(C13,C11,C10,C7,C5), C16(C14,C12,C9,C8,C6)
5.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2D,H2E,H2F), C1(H1D,H1E,H1F), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.80228(7) 0.750000 -0.25829(14) 0.0536(4) Uani 1 2 d S T P . .
Cl0A Cl 0.7873(6) 0.750000 0.3123(7) 0.0683(15) Uani 0.5 2 d S T P A 1
Cl1 Cl 0.81194(14) 0.81135(4) -0.2603(2) 0.0793(5) Uani 1 1 d . . . . .
Cl1A Cl 1.0889(4) 0.750000 -0.2697(10) 0.0735(14) Uani 0.5 2 d S T P B 1
Cl2 Cl 0.7885(6) 0.750000 0.1744(7) 0.0668(15) Uani 0.5 2 d S T P C 2
Cl3 Cl 1.0196(4) 0.750000 -0.2676(10) 0.0665(12) Uani 0.5 2 d S T P C 2
O1 O 0.8378(8) 0.9616(2) -0.1135(16) 0.137(2) Uani 0.759(10) 1 d D U . D 1
O2 O 0.934(2) 0.9663(6) -0.244(5) 0.131(3) Uani 0.241(10) 1 d D U . D 2
N1 N 1.0253(11) 0.8062(4) 0.229(3) 0.081(3) Uani 0.759(10) 1 d . U . D 1
H1A H 1.044473 0.802047 0.069350 0.097 Uiso 0.759(10) 1 calc GR . . D 1
H1B H 0.942604 0.806907 0.246639 0.097 Uiso 0.759(10) 1 calc GR . . D 1
H1C H 1.056492 0.788779 0.324629 0.097 Uiso 0.759(10) 1 calc GR . . D 1
N2 N 1.063(4) 0.8023(14) 0.206(11) 0.079(6) Uani 0.241(10) 1 d . U . D 2
H2D H 1.115075 0.789395 0.113328 0.095 Uiso 0.241(10) 1 calc GR . . D 2
H2E H 0.987160 0.802200 0.135252 0.095 Uiso 0.241(10) 1 calc GR . . D 2
H2F H 1.057626 0.792923 0.359219 0.095 Uiso 0.241(10) 1 calc GR . . D 2
C0 C 1.106(4) 0.8372(11) 0.222(6) 0.078(3) Uani 0.241(10) 1 d . U . D 2
H0A H 1.174678 0.839413 0.104951 0.094 Uiso 0.241(10) 1 calc R . . D 2
H0B H 1.140539 0.840212 0.388854 0.094 Uiso 0.241(10) 1 calc R . . D 2
C1 C 0.805(3) 0.9729(14) -0.277(10) 0.153(7) Uani 0.241(10) 1 d D U . D 2
H1D H 0.782670 0.968792 -0.448698 0.229 Uiso 0.241(10) 1 calc GR . . D 2
H1E H 0.786638 0.997359 -0.232940 0.229 Uiso 0.241(10) 1 calc GR . . D 2
H1F H 0.757778 0.957090 -0.170628 0.229 Uiso 0.241(10) 1 calc GR . . D 2
C2 C 0.8968(15) 0.9838(4) -0.297(3) 0.172(5) Uani 0.759(10) 1 d D U . D 1
H2A H 0.925820 0.969226 -0.433149 0.257 Uiso 0.759(10) 1 calc GR . . D 1
H2B H 0.966539 0.996021 -0.221638 0.257 Uiso 0.759(10) 1 calc GR . . D 1
H2C H 0.837922 1.001141 -0.358197 0.257 Uiso 0.759(10) 1 calc GR . . D 1
C009 C 1.0793(11) 0.8410(3) 0.3074(19) 0.082(3) Uani 0.759(10) 1 d . U . D 1
H00A H 1.169244 0.840365 0.284412 0.098 Uiso 0.759(10) 1 calc R . . D 1
H00B H 1.062623 0.844796 0.484261 0.098 Uiso 0.759(10) 1 calc R . . D 1
C15 C 0.9039(9) 0.9314(2) -0.0324(17) 0.109(2) Uani 0.759(10) 1 d D U . D 1
C13 C 0.8548(7) 0.9135(2) 0.1740(17) 0.103(2) Uani 0.759(10) 1 d G U . D 1
H13 H 0.781197 0.921557 0.247940 0.123 Uiso 0.759(10) 1 calc R . . D 1
C11 C 0.9158(8) 0.8836(2) 0.2700(17) 0.090(2) Uani 0.759(10) 1 d G U . D 1
H11 H 0.882979 0.871579 0.408111 0.108 Uiso 0.759(10) 1 calc R . . D 1
C10 C 1.0258(8) 0.8715(2) 0.1595(19) 0.0750(18) Uani 0.759(10) 1 d G U . D 1
C7 C 1.0749(7) 0.8895(3) -0.0470(18) 0.087(2) Uani 0.759(10) 1 d G U . D 1
H7 H 1.148524 0.881422 -0.120898 0.104 Uiso 0.759(10) 1 calc R . . D 1
C5 C 1.0139(8) 0.9194(2) -0.1429(15) 0.101(2) Uani 0.759(10) 1 d G U . D 1
H5 H 1.046744 0.931401 -0.281073 0.121 Uiso 0.759(10) 1 calc R . . D 1
C16 C 0.948(3) 0.9329(7) -0.105(6) 0.110(3) Uani 0.241(10) 1 d D U . D 2
C14 C 0.867(2) 0.9203(8) 0.079(6) 0.105(3) Uani 0.241(10) 1 d G U . D 2
H14 H 0.792342 0.932104 0.110408 0.126 Uiso 0.241(10) 1 calc R . . D 2
C12 C 0.899(3) 0.8899(9) 0.218(6) 0.088(3) Uani 0.241(10) 1 d G U . D 2
H12 H 0.844664 0.881480 0.340957 0.106 Uiso 0.241(10) 1 calc R . . D 2
C9 C 1.011(3) 0.8722(8) 0.171(7) 0.082(2) Uani 0.241(10) 1 d G U . D 2
C8 C 1.091(3) 0.8848(9) -0.013(7) 0.089(3) Uani 0.241(10) 1 d G U . D 2
H8 H 1.166439 0.873004 -0.043948 0.107 Uiso 0.241(10) 1 calc R . . D 2
C6 C 1.060(2) 0.9152(9) -0.151(5) 0.099(3) Uani 0.241(10) 1 d G U . D 2
H6 H 1.114119 0.923629 -0.274500 0.119 Uiso 0.241(10) 1 calc R . . D 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 Cl0A 2.294(4) 1_554 ?
Cu1 Cl1 2.2886(17) . ?
Cu1 Cl1 2.2886(17) 8_575 ?
Cu1 Cl1A 2.287(4) 6 ?
Cu1 Cl2 2.311(4) . ?
Cu1 Cl3 2.325(4) . ?
O1 C2 1.426(12) . ?
O1 C15 1.397(8) . ?
O2 C1 1.42(2) . ?
O2 C16 1.457(18) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C009 1.478(19) . ?
N2 H2D 0.8900 . ?
N2 H2E 0.8900 . ?
N2 H2F 0.8900 . ?
N2 C0 1.38(6) . ?
C0 H0A 0.9700 . ?
C0 H0B 0.9700 . ?
C0 C9 1.67(4) . ?
C1 H1D 0.9600 . ?
C1 H1E 0.9600 . ?
C1 H1F 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C009 H00A 0.9700 . ?
C009 H00B 0.9700 . ?
C009 C10 1.498(12) . ?
C15 C13 1.3900 . ?
C15 C5 1.3900 . ?
C13 H13 0.9300 . ?
C13 C11 1.3900 . ?
C11 H11 0.9300 . ?
C11 C10 1.3900 . ?
C10 C7 1.3900 . ?
C7 H7 0.9300 . ?
C7 C5 1.3900 . ?
C5 H5 0.9300 . ?
C16 C14 1.3900 . ?
C16 C6 1.3900 . ?
C14 H14 0.9300 . ?
C14 C12 1.3900 . ?
C12 H12 0.9300 . ?
C12 C9 1.3900 . ?
C9 C8 1.3900 . ?
C8 H8 0.9300 . ?
C8 C6 1.3900 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Cu1 Cl0A 89.92(4) 8_575 1_554 ?
Cl1 Cu1 Cl0A 89.92(4) . 1_554 ?
Cl1 Cu1 Cl1 174.80(8) 8_575 . ?
Cl1 Cu1 Cl2 90.43(4) . . ?
Cl1 Cu1 Cl2 90.43(4) 8_575 . ?
Cl1 Cu1 Cl3 87.41(4) 8_575 . ?
Cl1 Cu1 Cl3 87.41(4) . . ?
Cl1A Cu1 Cl0A 89.7(2) 6 1_554 ?
Cl1A Cu1 Cl1 92.60(4) 6 8_575 ?
Cl1A Cu1 Cl1 92.60(4) 6 . ?
Cl2 Cu1 Cl3 94.9(2) . . ?
C15 O1 C2 117.1(11) . . ?
C1 O2 C16 108(3) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C009 N1 H1A 109.5 . . ?
C009 N1 H1B 109.5 . . ?
C009 N1 H1C 109.5 . . ?
H2D N2 H2E 109.5 . . ?
H2D N2 H2F 109.5 . . ?
H2E N2 H2F 109.5 . . ?
C0 N2 H2D 109.5 . . ?
C0 N2 H2E 109.5 . . ?
C0 N2 H2F 109.5 . . ?
N2 C0 H0A 107.0 . . ?
N2 C0 H0B 107.0 . . ?
N2 C0 C9 121(3) . . ?
H0A C0 H0B 106.7 . . ?
C9 C0 H0A 107.0 . . ?
C9 C0 H0B 107.0 . . ?
O2 C1 H1D 109.5 . . ?
O2 C1 H1E 109.5 . . ?
O2 C1 H1F 109.5 . . ?
H1D C1 H1E 109.5 . . ?
H1D C1 H1F 109.5 . . ?
H1E C1 H1F 109.5 . . ?
O1 C2 H2A 109.5 . . ?
O1 C2 H2B 109.5 . . ?
O1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C009 H00A 109.3 . . ?
N1 C009 H00B 109.3 . . ?
N1 C009 C10 111.7(10) . . ?
H00A C009 H00B 107.9 . . ?
C10 C009 H00A 109.3 . . ?
C10 C009 H00B 109.3 . . ?
C13 C15 O1 116.2(6) . . ?
C13 C15 C5 120.0 . . ?
C5 C15 O1 123.8(6) . . ?
C15 C13 H13 120.0 . . ?
C15 C13 C11 120.0 . . ?
C11 C13 H13 120.0 . . ?
C13 C11 H11 120.0 . . ?
C10 C11 C13 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C10 C009 110.2(7) . . ?
C7 C10 C009 129.6(7) . . ?
C7 C10 C11 120.0 . . ?
C10 C7 H7 120.0 . . ?
C10 C7 C5 120.0 . . ?
C5 C7 H7 120.0 . . ?
C15 C5 H5 120.0 . . ?
C7 C5 C15 120.0 . . ?
C7 C5 H5 120.0 . . ?
C14 C16 O2 126(2) . . ?
C14 C16 C6 120.0 . . ?
C6 C16 O2 114(2) . . ?
C16 C14 H14 120.0 . . ?
C16 C14 C12 120.0 . . ?
C12 C14 H14 120.0 . . ?
C14 C12 H12 120.0 . . ?
C9 C12 C14 120.0 . . ?
C9 C12 H12 120.0 . . ?
C12 C9 C0 150(2) . . ?
C12 C9 C8 120.0 . . ?
C8 C9 C0 90(2) . . ?
C9 C8 H8 120.0 . . ?
C9 C8 C6 120.0 . . ?
C6 C8 H8 120.0 . . ?
C16 C6 H6 120.0 . . ?
C8 C6 C16 120.0 . . ?
C8 C6 H6 120.0 . . ?

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
O1 C15 C13 C11 -178.8(10) . . . . ?
O1 C15 C5 C7 178.7(11) . . . . ?
O2 C16 C14 C12 -173(4) . . . . ?
O2 C16 C6 C8 173(3) . . . . ?
N1 C009 C10 C11 86.3(10) . . . . ?
N1 C009 C10 C7 -98.8(12) . . . . ?
N2 C0 C9 C12 50(7) . . . . ?
N2 C0 C9 C8 -124(4) . . . . ?
C0 C9 C8 C6 176(3) . . . . ?
C1 O2 C16 C14 -34(4) . . . . ?
C1 O2 C16 C6 153(3) . . . . ?
C2 O1 C15 C13 169.8(10) . . . . ?
C2 O1 C15 C5 -9.0(15) . . . . ?
C009 C10 C7 C5 -174.4(13) . . . . ?
C15 C13 C11 C10 0.0 . . . . ?
C13 C15 C5 C7 0.0 . . . . ?
C13 C11 C10 C009 175.4(11) . . . . ?
C13 C11 C10 C7 0.0 . . . . ?
C11 C10 C7 C5 0.0 . . . . ?
C10 C7 C5 C15 0.0 . . . . ?
C5 C15 C13 C11 0.0 . . . . ?
C16 C14 C12 C9 0.0 . . . . ?
C14 C16 C6 C8 0.0 . . . . ?
C14 C12 C9 C0 -173(6) . . . . ?
C14 C12 C9 C8 0.0 . . . . ?
C12 C9 C8 C6 0.0 . . . . ?
C9 C8 C6 C16 0.0 . . . . ?
C6 C16 C14 C12 0.0 . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
