# 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. 
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data_mo_180629f_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 2261321'
loop_
_audit_author_name
_audit_author_address
'Zhichao Shao'
;Zhongyuan University of Technology
China
;
_audit_update_record             
;
2023-08-09 deposited with the CCDC.	2023-09-01 downloaded from the CCDC.
;
_audit_creation_date             2023-08-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H17 Cu N5 O5, N O3, H1.5 O0.5'
_chemical_formula_sum            'C21 H18 Cu N6 O8.50'
_chemical_formula_weight         553.95
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   10.3397(6)
_cell_length_b                   14.6943(8)
_cell_length_c                   14.9974(8)
_cell_angle_alpha                90
_cell_angle_beta                 90.685(2)
_cell_angle_gamma                90
_cell_volume                     2278.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9846
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.879
_exptl_absorpt_coefficient_mu    1.023
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0612 before and 0.0520 after correction.
The Ratio of minimum to maximum transmission is 0.9643.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            86105
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.597
_diffrn_reflns_theta_min         1.940
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4448
_reflns_number_total             5291
_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 v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.715
_refine_diff_density_min         -0.538
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     342
_refine_ls_number_reflns         5291
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0375
_refine_ls_restrained_S_all      1.089
_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)+(0.0520P)²+2.6777P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1006
_refine_ls_wR_factor_ref         0.1070
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O11-H11A
 0.85 with sigma of 0.02
 O11-H11B
 0.85 with sigma of 0.02
 H11A-H11B
 1.42 with sigma of 0.02
3. Others
 Fixed Sof: O11(0.5) H11A(0.5)
4.a Free rotating group:
 O11(H11A)
4.b Rotating group:
 O003(H00A,H00B)
4.c Secondary CH2 refined with riding coordinates:
 C00P(H00C,H00E)
4.d Aromatic/amide H refined with riding coordinates:
 C00D(H00D), C00H(H00H), C00I(H00I), C00J(H00J), C00M(H00M), C00O(H00O),
 C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V),
 C00W(H00W)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
Cu01 Cu 0.28891(2) 0.56376(2) 0.34635(2) 0.01655(9) Uani 1 1 d . . . . .
O002 O 0.25762(15) 0.66414(11) 0.43142(11) 0.0221(3) Uani 1 1 d . . . . .
O003 O 0.40312(16) 0.64430(12) 0.27428(11) 0.0254(4) Uani 1 1 d . . . . .
H00A H 0.431067 0.687766 0.306555 0.038 Uiso 1 1 d GR . . . .
H00B H 0.358182 0.670131 0.233763 0.038 Uiso 1 1 d GR . . . .
O004 O 0.62286(17) 0.91368(13) 0.75346(12) 0.0299(4) Uani 1 1 d . . . . .
O005 O 0.44851(18) 0.61290(12) 0.47795(14) 0.0354(5) Uani 1 1 d . . . . .
N006 N 0.27616(19) 0.87249(13) 0.61818(13) 0.0201(4) Uani 1 1 d . . . . .
O007 O 0.72059(18) 0.81538(17) 0.66259(14) 0.0450(6) Uani 1 1 d . . . . .
N008 N -0.1307(2) 0.04084(13) 0.78057(13) 0.0234(4) Uani 1 1 d . . . . .
N009 N 0.19544(19) 0.47331(13) 0.42313(13) 0.0211(4) Uani 1 1 d . . . . .
N00A N 0.0160(2) 0.26294(15) 0.56534(15) 0.0310(5) Uani 1 1 d . . . . .
N0B N 0.0577(2) 0.24940(16) 0.64212(16) 0.0344(5) Uani 1 1 d . . . . .
C00C C 0.4980(2) 0.83945(16) 0.64215(15) 0.0216(5) Uani 1 1 d . . . . .
C00D C 0.3899(2) 0.89068(15) 0.65944(15) 0.0222(5) Uani 1 1 d . . . . .
H00D H 0.395178 0.938397 0.700057 0.027 Uiso 1 1 calc R . . . .
C00E C 0.3596(2) 0.66865(15) 0.47920(15) 0.0215(5) Uani 1 1 d . . . . .
C00F C 0.3700(2) 0.74889(15) 0.54153(15) 0.0201(4) Uani 1 1 d . . . . .
C00G C 0.0792(2) 0.96255(17) 0.56694(16) 0.0238(5) Uani 1 1 d . . . . .
C00H C 0.2652(2) 0.80305(15) 0.55976(15) 0.0201(4) Uani 1 1 d . . . . .
H00H H 0.186213 0.791739 0.531619 0.024 Uiso 1 1 calc R . . . .
C00I C 0.4881(2) 0.76828(16) 0.58225(15) 0.0225(5) Uani 1 1 d . . . . .
H00I H 0.560528 0.733399 0.569211 0.027 Uiso 1 1 calc R . . . .
C00J C -0.0058(2) 0.06056(17) 0.79512(17) 0.0269(5) Uani 1 1 d . . . . .
H00J H 0.039943 0.026591 0.837229 0.032 Uiso 1 1 calc R . . . .
C00K C 0.0816(3) 0.33635(17) 0.52114(17) 0.0286(5) Uani 1 1 d . . . . .
C00L C -0.0101(3) 0.17745(17) 0.68627(17) 0.0282(5) Uani 1 1 d . . . . .
C00M C 0.0768(3) 0.44391(18) 0.40296(19) 0.0323(6) Uani 1 1 d . . . . .
H00M H 0.032489 0.470659 0.355423 0.039 Uiso 1 1 calc R . . . .
C00N C 0.6254(2) 0.85843(17) 0.69012(16) 0.0238(5) Uani 1 1 d . . . . .
C00O C 0.0581(3) 0.12887(18) 0.75061(17) 0.0299(5) Uani 1 1 d . . . . .
H00O H 0.144306 0.141972 0.763361 0.036 Uiso 1 1 calc R . . . .
C00P C 0.1591(2) 0.92618(17) 0.64399(16) 0.0270(5) Uani 1 1 d . . . . .
H00C H 0.186985 0.977076 0.680668 0.032 Uiso 1 1 calc R . . . .
H00E H 0.104431 0.887843 0.680279 0.032 Uiso 1 1 calc R . . . .
C00Q C -0.0452(3) 0.92989(18) 0.55215(18) 0.0301(5) Uani 1 1 d . . . . .
H00Q H -0.076471 0.882774 0.587235 0.036 Uiso 1 1 calc R . . . .
C00R C 0.1234(2) 1.03315(19) 0.51452(18) 0.0311(6) Uani 1 1 d . . . . .
H00R H 0.206240 1.056102 0.523999 0.037 Uiso 1 1 calc R . . . .
C00S C -0.1398(3) 0.15878(19) 0.67146(19) 0.0356(6) Uani 1 1 d . . . . .
H00S H -0.187541 0.191934 0.629768 0.043 Uiso 1 1 calc R . . . .
C00T C 0.0171(3) 0.3752(2) 0.4500(2) 0.0367(6) Uani 1 1 d . . . . .
H00T H -0.065403 0.355537 0.433764 0.044 Uiso 1 1 calc R . . . .
C00U C 0.2053(3) 0.3663(2) 0.54247(19) 0.0363(6) Uani 1 1 d . . . . .
H00U H 0.251500 0.340710 0.589818 0.044 Uiso 1 1 calc R . . . .
C00V C -0.1968(3) 0.0900(2) 0.71979(19) 0.0349(6) Uani 1 1 d . . . . .
H00V H -0.283874 0.077189 0.709947 0.042 Uiso 1 1 calc R . . . .
C00W C 0.2583(3) 0.43480(18) 0.49181(19) 0.0322(6) Uani 1 1 d . . . . .
H00W H 0.341164 0.455099 0.506013 0.039 Uiso 1 1 calc R . . . .
N0X N 0.5968(3) 0.8281(2) 0.2876(3) 0.0609(9) Uani 1 1 d . . . . .
O00Y O 0.6399(3) 0.7767(2) 0.2303(3) 0.0928(11) Uani 1 1 d . . . . .
O00Z O 0.5162(4) 0.7993(3) 0.3418(3) 0.1172(16) Uani 1 1 d . . . . .
O010 O 0.6335(4) 0.9059(2) 0.2890(4) 0.1314(19) Uani 1 1 d . . . . .
O11 O 0.4167(5) 0.9508(3) 0.4427(3) 0.0464(11) Uani 0.5 1 d D . P . .
H11A H 0.446924 0.985602 0.483090 0.070 Uiso 0.5 1 d DG . P . .
H11B H 0.471(3) 0.923(2) 0.416(2) 0.063(13) Uiso 1 1 d 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
Cu01 O002 1.9793(16) . ?
Cu01 O003 1.9985(16) . ?
Cu01 O004 2.2229(17) 4_575 ?
Cu01 N008 2.0117(19) 4_665 ?
Cu01 N009 2.0132(19) . ?
O002 C00E 1.269(3) . ?
O003 H00A 0.8499 . ?
O003 H00B 0.8499 . ?
O004 C00N 1.250(3) . ?
O005 C00E 1.232(3) . ?
N006 C00D 1.349(3) . ?
N006 C00H 1.349(3) . ?
N006 C00P 1.499(3) . ?
O007 C00N 1.244(3) . ?
N008 C00J 1.338(3) . ?
N008 C00V 1.343(3) . ?
N009 C00M 1.332(3) . ?
N009 C00W 1.337(3) . ?
N00A N0B 1.241(3) . ?
N00A C00K 1.440(3) . ?
N0B C00L 1.435(3) . ?
C00C C00D 1.375(3) . ?
C00C C00I 1.382(3) . ?
C00C C00N 1.519(3) . ?
C00D H00D 0.9300 . ?
C00E C00F 1.508(3) . ?
C00F C00H 1.374(3) . ?
C00F C00I 1.389(3) . ?
C00G C00P 1.511(3) . ?
C00G C00Q 1.388(4) . ?
C00G C00R 1.383(4) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00O 1.379(3) . ?
C00K C00T 1.376(4) . ?
C00K C00U 1.386(4) . ?
C00L C00O 1.386(4) . ?
C00L C00S 1.384(4) . ?
C00M H00M 0.9300 . ?
C00M C00T 1.381(4) . ?
C00O H00O 0.9300 . ?
C00P H00C 0.9700 . ?
C00P H00E 0.9700 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.389(4) 3_576 ?
C00R H00R 0.9300 . ?
C00S H00S 0.9300 . ?
C00S C00V 1.380(4) . ?
C00T H00T 0.9300 . ?
C00U H00U 0.9300 . ?
C00U C00W 1.379(4) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
N0X O00Y 1.231(4) . ?
N0X O00Z 1.245(5) . ?
N0X O010 1.205(4) . ?
O11 H11A 0.8500 . ?
O11 H11B 0.809(18) . ?

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
O002 Cu01 O003 90.54(7) . . ?
O002 Cu01 O004 99.31(7) . 4_575 ?
O002 Cu01 N008 163.17(8) . 4_665 ?
O002 Cu01 N009 92.29(7) . . ?
O003 Cu01 O004 91.70(7) . 4_575 ?
O003 Cu01 N008 86.38(8) . 4_665 ?
O003 Cu01 N009 172.36(8) . . ?
N008 Cu01 O004 97.31(8) 4_665 4_575 ?
N008 Cu01 N009 88.86(8) 4_665 . ?
N009 Cu01 O004 94.84(7) . 4_575 ?
C00E O002 Cu01 105.18(14) . . ?
Cu01 O003 H00A 109.6 . . ?
Cu01 O003 H00B 109.2 . . ?
H00A O003 H00B 104.5 . . ?
C00N O004 Cu01 123.36(16) . 4_676 ?
C00D N006 C00H 120.9(2) . . ?
C00D N006 C00P 118.62(19) . . ?
C00H N006 C00P 120.3(2) . . ?
C00J N008 Cu01 119.27(16) . 4_566 ?
C00J N008 C00V 118.4(2) . . ?
C00V N008 Cu01 122.23(18) . 4_566 ?
C00M N009 Cu01 122.10(17) . . ?
C00M N009 C00W 118.4(2) . . ?
C00W N009 Cu01 119.21(17) . . ?
N0B N00A C00K 112.7(2) . . ?
N00A N0B C00L 112.3(2) . . ?
C00D C00C C00I 118.9(2) . . ?
C00D C00C C00N 120.8(2) . . ?
C00I C00C C00N 120.3(2) . . ?
N006 C00D C00C 120.7(2) . . ?
N006 C00D H00D 119.6 . . ?
C00C C00D H00D 119.6 . . ?
O002 C00E C00F 116.3(2) . . ?
O005 C00E O002 124.9(2) . . ?
O005 C00E C00F 118.8(2) . . ?
C00H C00F C00E 121.7(2) . . ?
C00H C00F C00I 119.0(2) . . ?
C00I C00F C00E 119.3(2) . . ?
C00Q C00G C00P 119.8(2) . . ?
C00R C00G C00P 121.2(2) . . ?
C00R C00G C00Q 118.7(2) . . ?
N006 C00H C00F 120.5(2) . . ?
N006 C00H H00H 119.8 . . ?
C00F C00H H00H 119.8 . . ?
C00C C00I C00F 119.9(2) . . ?
C00C C00I H00I 120.0 . . ?
C00F C00I H00I 120.0 . . ?
N008 C00J H00J 118.5 . . ?
N008 C00J C00O 123.1(2) . . ?
C00O C00J H00J 118.5 . . ?
C00T C00K N00A 116.1(2) . . ?
C00T C00K C00U 119.0(2) . . ?
C00U C00K N00A 124.7(2) . . ?
C00O C00L N0B 117.0(2) . . ?
C00S C00L N0B 123.4(2) . . ?
C00S C00L C00O 119.6(2) . . ?
N009 C00M H00M 118.7 . . ?
N009 C00M C00T 122.5(2) . . ?
C00T C00M H00M 118.7 . . ?
O004 C00N C00C 116.9(2) . . ?
O007 C00N O004 127.3(2) . . ?
O007 C00N C00C 115.7(2) . . ?
C00J C00O C00L 118.0(2) . . ?
C00J C00O H00O 121.0 . . ?
C00L C00O H00O 121.0 . . ?
N006 C00P C00G 115.13(19) . . ?
N006 C00P H00C 108.5 . . ?
N006 C00P H00E 108.5 . . ?
C00G C00P H00C 108.5 . . ?
C00G C00P H00E 108.5 . . ?
H00C C00P H00E 107.5 . . ?
C00G C00Q H00Q 119.7 . . ?
C00G C00Q C00R 120.7(2) . 3_576 ?
C00R C00Q H00Q 119.7 3_576 . ?
C00G C00R C00Q 120.6(2) . 3_576 ?
C00G C00R H00R 119.7 . . ?
C00Q C00R H00R 119.7 3_576 . ?
C00L C00S H00S 120.7 . . ?
C00V C00S C00L 118.7(2) . . ?
C00V C00S H00S 120.7 . . ?
C00K C00T C00M 118.9(3) . . ?
C00K C00T H00T 120.5 . . ?
C00M C00T H00T 120.5 . . ?
C00K C00U H00U 120.8 . . ?
C00W C00U C00K 118.4(2) . . ?
C00W C00U H00U 120.8 . . ?
N008 C00V C00S 122.2(3) . . ?
N008 C00V H00V 118.9 . . ?
C00S C00V H00V 118.9 . . ?
N009 C00W C00U 122.8(2) . . ?
N009 C00W H00W 118.6 . . ?
C00U C00W H00W 118.6 . . ?
O00Y N0X O00Z 119.8(3) . . ?
O010 N0X O00Y 118.5(4) . . ?
O010 N0X O00Z 121.6(4) . . ?
H11A O11 H11B 113.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
