# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ch3_cudbc_0m
_database_code_depnum_ccdc_archive 'CCDC 2261491'
loop_
_audit_author_name
_audit_author_address
'Yuxin Wang'
;Taiyuan University of Technology
China
;
_audit_update_record             
;
2023-05-09 deposited with the CCDC.	2024-03-12 downloaded from the CCDC.
;
_audit_creation_date             2023-04-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_shelx_SHELXL_version_number     2019/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Cu N O5'
_chemical_formula_sum            'C12 H10 Cu N O5'
_chemical_formula_weight         311.75
_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 0.0137 0.0067 '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 -2.7974 3.6876 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0389 0.0241 '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           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.083(9)
_cell_length_b                   16.140(11)
_cell_length_c                   7.938(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.67(4)
_cell_angle_gamma                90
_cell_volume                     1268.8(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1549
_cell_measurement_temperature    150
_cell_measurement_theta_max      41.64
_cell_measurement_theta_min      4.56
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.403
_exptl_absorpt_correction_T_max  0.7483
_exptl_absorpt_correction_T_min  0.4910
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1280 before and 0.0736 after correction.
The Ratio of minimum to maximum transmission is 0.6562.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.632
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             632
_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  0.0709
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            2828
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        41.780
_diffrn_reflns_theta_max         41.780
_diffrn_reflns_theta_min         4.557
_diffrn_ambient_temperature      150.00
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker SMART CCD 1K area detector'
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_source                   ?
_diffrn_source_current           2.0
_diffrn_source_power             0.13972
_diffrn_source_voltage           69.86
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                574
_reflns_number_total             672
_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 V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.124
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         672
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0884
_refine_ls_R_factor_gt           0.0796
_refine_ls_restrained_S_all      1.109
_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)+(0.1266P)²+15.1831P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2198
_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 C(H,H,H) groups
2. Restrained distances
 C1-C2
 1.45 with sigma of 0.02
 N1-N1_$1
 2.5 with sigma of 0.02
 C6_$1-C7
 2.5 with sigma of 0.02
 C6-C7
 2.5 with sigma of 0.02
 C6-C6_$1
 2.5 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O3 \\sim C6 \\sim N1 \\sim C8 \\sim C7 \\sim N1 \\sim C8 \\sim C6: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Fixed Sof: N1(0.5) C6(0.5) H6(0.5) C1(0.5) H1A(0.5) H1B(0.5) H1C(0.5) C8(0.5)
 H8A(0.5) H8B(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
5.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6)
5.c X=CH2 refined with riding coordinates:
 C8(H8A,H8B)
5.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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 0.40414(19) 0.500000 0.0547(3) 0.0376(10) Uani 1 2 d S T P . .
O2 O 0.5148(8) 0.5863(4) 0.2299(10) 0.052(2) Uani 1 1 d . . . . .
O1 O 0.6804(8) 0.5866(5) 0.1416(10) 0.055(2) Uani 1 1 d . . . . .
O3 O 0.2478(13) 0.500000 0.1494(17) 0.079(4) Uani 1 2 d S TU P . .
C3 C 0.6916(11) 0.6840(7) 0.3735(15) 0.047(3) Uani 1 1 d . . . . .
C5 C 0.6228(12) 0.6125(6) 0.2385(14) 0.040(3) Uani 1 1 d . . . . .
C2 C 0.7721(13) 0.7425(7) 0.3392(15) 0.058(3) Uani 1 1 d D . . . .
C4 C 0.6712(13) 0.6930(7) 0.5321(17) 0.060(3) Uani 1 1 d . . . . .
H4 H 0.616207 0.653633 0.554284 0.072 Uiso 1 1 calc R U . . .
C7 C 0.084(2) 0.500000 0.323(4) 0.118(7) Uani 1 2 d DS TU P . .
H7A H 0.163795 0.500000 0.447471 0.141 Uiso 1 2 calc R U P . .
H7B H 0.001212 0.500000 0.341943 0.141 Uiso 1 2 calc R U P . .
N1 N 0.085(3) 0.4253(6) 0.207(4) 0.101(5) Uani 0.5 1 d D U P . .
C6 C 0.170(3) 0.4244(6) 0.125(4) 0.093(5) Uani 0.5 1 d D U P . .
H6 H 0.177673 0.377910 0.057151 0.112 Uiso 0.5 1 calc R U P . .
C1 C 0.802(4) 0.738(2) 0.179(4) 0.121(14) Uani 0.5 1 d D . P . .
H1A H 0.881208 0.702691 0.211132 0.181 Uiso 0.5 1 calc R U P . .
H1B H 0.820862 0.793840 0.148238 0.181 Uiso 0.5 1 calc R U P . .
H1C H 0.724418 0.714731 0.070678 0.181 Uiso 0.5 1 calc R U P . .
C8 C 0.001(3) 0.377(2) 0.196(5) 0.110(9) Uani 0.5 1 d . U P . .
H8A H -0.014978 0.329135 0.120196 0.132 Uiso 0.5 1 calc R U P . .
H8B H -0.050160 0.387076 0.262962 0.132 Uiso 0.5 1 calc R U P . .


_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 Cu1 2.632(4) 5_665 ?
Cu1 O2 1.961(7) 6_565 ?
Cu1 O2 1.961(7) . ?
Cu1 O1 1.987(7) 2_655 ?
Cu1 O1 1.987(7) 5_665 ?
Cu1 O3 2.176(12) . ?
O2 C5 1.243(12) . ?
O1 C5 1.271(13) . ?
O3 C6 1.457(18) . ?
O3 C6 1.457(18) 6_565 ?
C3 C5 1.525(15) . ?
C3 C2 1.408(15) . ?
C3 C4 1.382(16) . ?
C2 C4 1.395(16) 7_666 ?
C2 C1 1.451(18) . ?
C4 H4 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 N1 1.52(2) . ?
C7 N1 1.52(2) 6_565 ?
N1 C6 1.36(3) . ?
N1 C8 1.18(3) . ?
C6 H6 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C8 H8A 0.9500 . ?
C8 H8B 0.9500 . ?

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
O2 Cu1 Cu1 83.9(2) . 5_665 ?
O2 Cu1 Cu1 83.9(2) 6_565 5_665 ?
O2 Cu1 O2 90.5(5) 6_565 . ?
O2 Cu1 O1 168.6(3) 6_565 2_655 ?
O2 Cu1 O1 88.9(4) 6_565 5_665 ?
O2 Cu1 O1 168.6(3) . 5_665 ?
O2 Cu1 O1 88.9(4) . 2_655 ?
O2 Cu1 O3 95.5(3) . . ?
O2 Cu1 O3 95.5(3) 6_565 . ?
O1 Cu1 Cu1 84.7(3) 5_665 5_665 ?
O1 Cu1 Cu1 84.7(3) 2_655 5_665 ?
O1 Cu1 O1 89.4(5) 5_665 2_655 ?
O1 Cu1 O3 95.9(3) 5_665 . ?
O1 Cu1 O3 95.9(3) 2_655 . ?
O3 Cu1 Cu1 179.2(3) . 5_665 ?
C5 O2 Cu1 124.1(7) . . ?
C5 O1 Cu1 121.2(7) . 5_665 ?
C6 O3 Cu1 118.1(9) 6_565 . ?
C6 O3 Cu1 118.1(9) . . ?
C6 O3 C6 113.8(19) . 6_565 ?
C2 C3 C5 122.1(10) . . ?
C4 C3 C5 119.0(10) . . ?
C4 C3 C2 118.8(10) . . ?
O2 C5 O1 126.0(9) . . ?
O2 C5 C3 117.4(10) . . ?
O1 C5 C3 116.5(10) . . ?
C3 C2 C1 123.4(15) . . ?
C4 C2 C3 118.4(10) 7_666 . ?
C4 C2 C1 118.2(15) 7_666 . ?
C3 C4 C2 122.8(11) . 7_666 ?
C3 C4 H4 118.6 . . ?
C2 C4 H4 118.6 7_666 . ?
H7A C7 H7B 108.9 . . ?
N1 C7 H7A 110.8 6_565 . ?
N1 C7 H7A 110.8 . . ?
N1 C7 H7B 110.8 6_565 . ?
N1 C7 H7B 110.8 . . ?
N1 C7 N1 105(2) . 6_565 ?
C6 N1 C7 119.7(15) . . ?
C8 N1 C7 110(3) . . ?
C8 N1 C6 130(3) . . ?
O3 C6 H6 122.5 . . ?
N1 C6 O3 115.0(13) . . ?
N1 C6 H6 122.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C8 H8A 120.0 . . ?
N1 C8 H8B 120.0 . . ?
H8A C8 H8B 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
Cu1 O2 C5 O1 -2.3(16) . . . . ?
Cu1 O2 C5 C3 176.0(6) . . . . ?
Cu1 O1 C5 O2 3.1(15) 5_665 . . . ?
Cu1 O1 C5 C3 -175.2(6) 5_665 . . . ?
Cu1 O3 C6 N1 172.6(17) . . . . ?
C5 C3 C2 C4 178.6(10) . . . 7_666 ?
C5 C3 C2 C1 -3(3) . . . . ?
C5 C3 C4 C2 -178.7(10) . . . 7_666 ?
C2 C3 C5 O2 -150.2(11) . . . . ?
C2 C3 C5 O1 28.2(15) . . . . ?
C2 C3 C4 C2 0(2) . . . 7_666 ?
C4 C3 C5 O2 28.0(15) . . . . ?
C4 C3 C5 O1 -153.6(11) . . . . ?
C4 C3 C2 C4 0.4(19) . . . 7_666 ?
C4 C3 C2 C1 179(2) . . . . ?
C7 N1 C6 O3 -3(3) . . . . ?
N1 C7 N1 C6 44(4) 6_565 . . . ?
N1 C7 N1 C8 -132(2) 6_565 . . . ?
C6 O3 C6 N1 -43(4) 6_565 . . . ?
C8 N1 C6 O3 172(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
