# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2021

####################################################################### 
# 
# 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_mmcutmq
_database_code_depnum_ccdc_archive 'CCDC 1562459'
_audit_update_record             
;
2017-07-16 deposited with the CCDC.	2021-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 Cl Cu N4 O5'
_chemical_formula_weight         554.43

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'
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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.3527(8)
_cell_length_b                   12.8535(14)
_cell_length_c                   13.2223(15)
_cell_angle_alpha                75.187(2)
_cell_angle_beta                 79.635(2)
_cell_angle_gamma                86.841(2)
_cell_volume                     1188.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9369
_cell_measurement_theta_min      1.62
_cell_measurement_theta_max      29.01

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.550
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             566
_exptl_absorpt_coefficient_mu    1.077
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.702316
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'Bruker AXS SADABS'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER AXS SMART 1000'
_diffrn_measurement_method       omega-scan
_diffrn_detector_area_resol_mean '8.192 pixels/mm'
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            17029
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.62
_diffrn_reflns_theta_max         29.01
_reflns_number_total             6274
_reflns_number_gt                4623
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       SMART
_computing_cell_refinement       ?
_computing_data_reduction        'SAINT (Bruker, 1998)'
_computing_structure_solution    'SIR97 (Giacovazzo et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0539P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6274
_refine_ls_number_parameters     391
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0939
_refine_ls_wR_factor_gt          0.0890
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.20837(3) 0.246112(18) 0.234418(17) 0.04793(9) Uani 1 1 d . . .
N1 N 0.26226(19) 0.41672(12) 0.23605(12) 0.0459(3) Uani 1 1 d . . .
N2 N 0.42859(19) 0.17860(12) 0.17258(11) 0.0432(3) Uani 1 1 d . . .
N3 N 0.1567(2) 0.26217(13) 0.08430(13) 0.0527(4) Uani 1 1 d . . .
N4 N 0.3330(2) 0.18755(12) 0.36599(12) 0.0510(4) Uani 1 1 d . . .
O1 O -0.03212(18) 0.28339(11) 0.29586(12) 0.0607(4) Uani 1 1 d . . .
C1 C 0.4093(3) 0.47893(16) 0.20979(16) 0.0543(4) Uani 1 1 d . . .
C2 C 0.4088(3) 0.57489(18) 0.2430(2) 0.0693(6) Uani 1 1 d . . .
C3 C 0.2540(4) 0.60718(18) 0.2996(2) 0.0686(6) Uani 1 1 d . . .
C4 C 0.0934(3) 0.54455(15) 0.32769(15) 0.0532(4) Uani 1 1 d . . .
C5 C -0.0741(3) 0.57205(19) 0.38552(18) 0.0647(6) Uani 1 1 d . . .
C6 C -0.2197(3) 0.50526(19) 0.41003(18) 0.0670(6) Uani 1 1 d . . .
C7 C -0.2096(3) 0.40720(19) 0.38062(18) 0.0624(5) Uani 1 1 d . . .
C8 C -0.0478(2) 0.37528(15) 0.32396(15) 0.0500(4) Uani 1 1 d . . .
C9 C 0.1065(2) 0.44729(14) 0.29518(13) 0.0441(4) Uani 1 1 d . . .
C10 C 0.5793(3) 0.4437(2) 0.1443(2) 0.0724(6) Uani 1 1 d . . .
H10A H 0.6513 0.3954 0.1902 0.109 Uiso 1 1 calc R . .
H10B H 0.6518 0.5055 0.1050 0.109 Uiso 1 1 calc R . .
H10C H 0.5432 0.4077 0.0958 0.109 Uiso 1 1 calc R . .
C11 C 0.4440(2) 0.16936(14) 0.07260(14) 0.0465(4) Uani 1 1 d . . .
C12 C 0.5963(3) 0.11859(18) 0.02748(17) 0.0584(5) Uani 1 1 d . . .
C13 C 0.7311(3) 0.07917(19) 0.08761(18) 0.0661(6) Uani 1 1 d . . .
C14 C 0.7126(3) 0.08801(18) 0.19088(19) 0.0603(5) Uani 1 1 d . . .
C15 C 0.5566(2) 0.13791(14) 0.23264(14) 0.0466(4) Uani 1 1 d . . .
C16 C 0.2845(3) 0.21681(15) 0.02170(14) 0.0487(4) Uani 1 1 d . . .
C17 C 0.2646(3) 0.21578(19) -0.07987(17) 0.0614(5) Uani 1 1 d . . .
C18 C 0.1105(4) 0.2658(2) -0.1188(2) 0.0754(7) Uani 1 1 d . . .
C19 C -0.0144(4) 0.3149(3) -0.0571(2) 0.0811(8) Uani 1 1 d . . .
C20 C 0.0093(3) 0.3115(2) 0.0440(2) 0.0698(6) Uani 1 1 d . . .
C21 C 0.5060(3) 0.14966(14) 0.34252(14) 0.0477(4) Uani 1 1 d . . .
C22 C 0.6240(3) 0.12330(18) 0.41600(18) 0.0626(5) Uani 1 1 d . . .
C23 C 0.5581(5) 0.1341(2) 0.5177(2) 0.0781(7) Uani 1 1 d . . .
C24 C 0.3797(5) 0.1695(2) 0.54278(19) 0.0783(7) Uani 1 1 d . . .
C25 C 0.2708(4) 0.19604(19) 0.46541(17) 0.0649(6) Uani 1 1 d . . .
Cl1 Cl 0.15350(6) -0.06936(4) 0.24780(3) 0.04946(11) Uani 1 1 d . . .
O2 O 0.3424(2) -0.10283(16) 0.23896(13) 0.0828(5) Uani 1 1 d . . .
O3 O 0.0363(3) -0.15602(15) 0.30004(18) 0.1094(8) Uani 1 1 d . . .
O4 O 0.1160(3) -0.02617(18) 0.14291(13) 0.1006(7) Uani 1 1 d . . .
O5 O 0.1196(3) 0.01264(15) 0.30337(16) 0.0885(5) Uani 1 1 d . . .
H2 H 0.517(3) 0.6168(18) 0.2264(18) 0.068(6) Uiso 1 1 d . . .
H3 H 0.257(3) 0.6712(18) 0.3291(18) 0.066(6) Uiso 1 1 d . . .
H5 H -0.078(3) 0.6309(17) 0.4070(17) 0.060(6) Uiso 1 1 d . . .
H6 H -0.334(3) 0.5246(18) 0.4506(18) 0.072(7) Uiso 1 1 d . . .
H7 H -0.321(3) 0.3638(17) 0.4014(17) 0.066(6) Uiso 1 1 d . . .
H12 H 0.602(3) 0.1095(16) -0.0398(17) 0.056(6) Uiso 1 1 d . . .
H13 H 0.837(3) 0.0461(18) 0.0622(18) 0.067(6) Uiso 1 1 d . . .
H14 H 0.797(3) 0.0693(18) 0.2276(19) 0.072(7) Uiso 1 1 d . . .
H17 H 0.349(3) 0.1834(17) -0.1178(18) 0.059(6) Uiso 1 1 d . . .
H18 H 0.097(4) 0.264(2) -0.186(2) 0.097(9) Uiso 1 1 d . . .
H19 H -0.108(4) 0.353(2) -0.076(2) 0.096(9) Uiso 1 1 d . . .
H20 H -0.062(3) 0.3435(19) 0.084(2) 0.071(7) Uiso 1 1 d . . .
H22 H 0.744(3) 0.0981(15) 0.3988(15) 0.045(5) Uiso 1 1 d . . .
H23 H 0.631(3) 0.1214(18) 0.5638(18) 0.065(6) Uiso 1 1 d . . .
H24 H 0.331(4) 0.172(2) 0.614(2) 0.093(8) Uiso 1 1 d . . .
H25 H 0.158(3) 0.2223(17) 0.4796(16) 0.056(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
Cu1 O1 1.8987(13) . ?
Cu1 N2 1.9429(14) . ?
Cu1 N3 2.0445(16) . ?
Cu1 N4 2.0640(16) . ?
Cu1 N1 2.2560(15) . ?
N1 C1 1.322(2) . ?
N1 C9 1.365(2) . ?
N2 C15 1.339(2) . ?
N2 C11 1.341(2) . ?
N3 C16 1.347(2) . ?
N3 C20 1.349(3) . ?
N4 C25 1.342(2) . ?
N4 C21 1.349(2) . ?
O1 C8 1.319(2) . ?
C1 C2 1.411(3) . ?
C1 C10 1.506(3) . ?
C2 C3 1.352(3) . ?
C2 H2 0.95(2) . ?
C3 C4 1.405(3) . ?
C3 H3 1.00(2) . ?
C4 C5 1.406(3) . ?
C4 C9 1.416(3) . ?
C5 C6 1.350(3) . ?
C5 H5 0.87(2) . ?
C6 C7 1.406(3) . ?
C6 H6 0.97(2) . ?
C7 C8 1.388(3) . ?
C7 H7 0.98(2) . ?
C8 C9 1.439(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.384(2) . ?
C11 C16 1.482(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.92(2) . ?
C13 C14 1.381(3) . ?
C13 H13 0.92(2) . ?
C14 C15 1.380(3) . ?
C14 H14 0.84(2) . ?
C15 C21 1.478(2) . ?
C16 C17 1.380(3) . ?
C17 C18 1.386(3) . ?
C17 H17 0.88(2) . ?
C18 C19 1.356(4) . ?
C18 H18 0.92(3) . ?
C19 C20 1.368(4) . ?
C19 H19 0.86(3) . ?
C20 H20 0.85(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.385(3) . ?
C22 H22 0.935(19) . ?
C23 C24 1.375(4) . ?
C23 H23 0.86(2) . ?
C24 C25 1.375(4) . ?
C24 H24 0.96(3) . ?
C25 H25 0.89(2) . ?
Cl1 O3 1.3996(18) . ?
Cl1 O5 1.4192(16) . ?
Cl1 O2 1.4245(15) . ?
Cl1 O4 1.4266(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 N2 167.35(6) . . ?
O1 Cu1 N3 97.35(6) . . ?
N2 Cu1 N3 79.26(6) . . ?
O1 Cu1 N4 102.26(7) . . ?
N2 Cu1 N4 79.27(6) . . ?
N3 Cu1 N4 157.64(6) . . ?
O1 Cu1 N1 80.95(5) . . ?
N2 Cu1 N1 111.66(6) . . ?
N3 Cu1 N1 102.99(6) . . ?
N4 Cu1 N1 90.70(6) . . ?
C1 N1 C9 118.98(16) . . ?
C1 N1 Cu1 135.09(13) . . ?
C9 N1 Cu1 104.80(11) . . ?
C15 N2 C11 121.78(15) . . ?
C15 N2 Cu1 119.04(12) . . ?
C11 N2 Cu1 119.10(12) . . ?
C16 N3 C20 118.34(19) . . ?
C16 N3 Cu1 114.95(12) . . ?
C20 N3 Cu1 126.71(16) . . ?
C25 N4 C21 118.67(18) . . ?
C25 N4 Cu1 127.34(16) . . ?
C21 N4 Cu1 113.39(12) . . ?
C8 O1 Cu1 116.30(11) . . ?
N1 C1 C2 121.33(19) . . ?
N1 C1 C10 118.02(18) . . ?
C2 C1 C10 120.64(19) . . ?
C3 C2 C1 120.2(2) . . ?
C3 C2 H2 119.6(14) . . ?
C1 C2 H2 120.3(14) . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 120.0(13) . . ?
C4 C3 H3 119.2(13) . . ?
C3 C4 C5 124.42(19) . . ?
C3 C4 C9 116.17(18) . . ?
C5 C4 C9 119.41(19) . . ?
C6 C5 C4 119.8(2) . . ?
C6 C5 H5 122.2(15) . . ?
C4 C5 H5 117.9(15) . . ?
C5 C6 C7 122.1(2) . . ?
C5 C6 H6 119.1(14) . . ?
C7 C6 H6 118.8(14) . . ?
C8 C7 C6 120.9(2) . . ?
C8 C7 H7 122.3(13) . . ?
C6 C7 H7 116.8(13) . . ?
O1 C8 C7 122.75(18) . . ?
O1 C8 C9 119.88(15) . . ?
C7 C8 C9 117.37(17) . . ?
N1 C9 C4 122.85(16) . . ?
N1 C9 C8 116.71(15) . . ?
C4 C9 C8 120.44(16) . . ?
C1 C10 H10A 109.5 . . ?
C1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 120.49(17) . . ?
N2 C11 C16 112.97(15) . . ?
C12 C11 C16 126.54(17) . . ?
C13 C12 C11 118.13(19) . . ?
C13 C12 H12 122.4(13) . . ?
C11 C12 H12 119.4(13) . . ?
C12 C13 C14 120.84(19) . . ?
C12 C13 H13 122.9(14) . . ?
C14 C13 H13 116.3(14) . . ?
C15 C14 C13 118.7(2) . . ?
C15 C14 H14 118.4(17) . . ?
C13 C14 H14 122.7(16) . . ?
N2 C15 C14 120.02(18) . . ?
N2 C15 C21 113.00(15) . . ?
C14 C15 C21 126.94(18) . . ?
N3 C16 C17 121.93(19) . . ?
N3 C16 C11 113.60(16) . . ?
C17 C16 C11 124.47(18) . . ?
C16 C17 C18 118.5(2) . . ?
C16 C17 H17 119.5(15) . . ?
C18 C17 H17 122.0(15) . . ?
C19 C18 C17 119.5(2) . . ?
C19 C18 H18 122.2(18) . . ?
C17 C18 H18 118.3(18) . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 126(2) . . ?
C20 C19 H19 114(2) . . ?
N3 C20 C19 121.9(3) . . ?
N3 C20 H20 114.9(17) . . ?
C19 C20 H20 123.1(17) . . ?
N4 C21 C22 122.41(18) . . ?
N4 C21 C15 114.18(16) . . ?
C22 C21 C15 123.41(19) . . ?
C21 C22 C23 118.0(2) . . ?
C21 C22 H22 121.9(12) . . ?
C23 C22 H22 120.1(12) . . ?
C24 C23 C22 119.7(2) . . ?
C24 C23 H23 120.8(16) . . ?
C22 C23 H23 119.4(16) . . ?
C25 C24 C23 119.3(2) . . ?
C25 C24 H24 120.6(17) . . ?
C23 C24 H24 120.0(17) . . ?
N4 C25 C24 121.9(2) . . ?
N4 C25 H25 117.9(14) . . ?
C24 C25 H25 120.2(14) . . ?
O3 Cl1 O5 109.23(12) . . ?
O3 Cl1 O2 111.02(13) . . ?
O5 Cl1 O2 110.95(12) . . ?
O3 Cl1 O4 109.74(14) . . ?
O5 Cl1 O4 108.20(12) . . ?
O2 Cl1 O4 107.64(10) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        29.01
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.050
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeCN:MeOH'
