# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_compound_M1
_database_code_depnum_ccdc_archive 'CCDC 1830264'
loop_
_audit_author_name
_audit_author_address
'Vitor Felix'
;University of Aveiro
Portugal
;
_audit_update_record             
;
2020-02-21 deposited with the CCDC.	2020-04-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cu N2 O3'
_chemical_formula_weight         317.78

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

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

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

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

_cell_length_a                   6.4066(6)
_cell_length_b                   18.6435(16)
_cell_length_c                   9.8389(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.696(3)
_cell_angle_gamma                90
_cell_volume                     1167.16(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    486
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      25.08

_exptl_crystal_description       plate
_exptl_crystal_colour            bronze
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.808
_exptl_crystal_F_000             644
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.879
_shelx_estimated_absorpt_T_min   0.753
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5998
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD diffractometer'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20090
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0674
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.185
_diffrn_reflns_theta_max         27.121
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.956
_reflns_number_total             2477
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Mercury (Macrae et al 2008)'
_computing_publication_material  'Olex2(Dolomanov et al 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0690P)²+3.7447P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2477
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0711
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1461
_refine_ls_wR_factor_gt          0.1377
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.19048(8) 0.54477(3) 0.48520(6) 0.0180(2) Uani 1 1 d . . . . .
O17 O 0.0085(5) 0.47591(17) 0.3811(3) 0.0177(6) Uani 1 1 d . . . . .
O19 O 0.9372(5) 0.64346(17) 0.3915(3) 0.0196(7) Uani 1 1 d . . . . .
O18 O 0.3830(5) 0.61428(17) 0.5737(3) 0.0200(7) Uani 1 1 d . . . . .
N9 N 0.5695(5) 0.5864(2) 0.3951(4) 0.0184(8) Uani 1 1 d . . . . .
H9 H 0.681562 0.588406 0.351335 0.022 Uiso 1 1 calc R U . . .
N8 N 0.3929(5) 0.5445(2) 0.3564(4) 0.0173(7) Uani 1 1 d . . . . .
C10 C 0.5438(7) 0.6227(2) 0.5076(5) 0.0169(9) Uani 1 1 d . . . . .
C1 C 0.0333(7) 0.4492(2) 0.2566(5) 0.0172(9) Uani 1 1 d . . . . .
C12 C 0.8912(7) 0.6843(2) 0.4979(5) 0.0179(9) Uani 1 1 d . . . . .
C6 C 0.2140(7) 0.4637(2) 0.1888(5) 0.0173(9) Uani 1 1 d . . . . .
C16 C 0.6726(7) 0.7184(2) 0.6704(5) 0.0188(9) Uani 1 1 d . . . . .
H16 H 0.547264 0.712941 0.712347 0.023 Uiso 1 1 calc R U . . .
C7 C 0.3868(7) 0.5088(2) 0.2441(4) 0.0176(9) Uani 1 1 d . . . . .
H7 H 0.504450 0.512308 0.193932 0.021 Uiso 1 1 calc R U . . .
C11 C 0.7045(7) 0.6752(2) 0.5592(4) 0.0176(9) Uani 1 1 d . . . . .
C13 C 1.0376(7) 0.7353(3) 0.5483(5) 0.0219(10) Uani 1 1 d . . . . .
H13 H 1.162258 0.741896 0.506176 0.026 Uiso 1 1 calc R U . . .
C15 C 0.8181(7) 0.7690(3) 0.7210(5) 0.0228(10) Uani 1 1 d . . . . .
H15 H 0.792962 0.798278 0.796455 0.027 Uiso 1 1 calc R U . . .
C14 C 1.0018(7) 0.7767(3) 0.6605(5) 0.0240(10) Uani 1 1 d . . . . .
H14 H 1.104304 0.810688 0.696244 0.029 Uiso 1 1 calc R U . . .
C2 C -0.1228(7) 0.4052(3) 0.1898(5) 0.0217(10) Uani 1 1 d . . . . .
H2 H -0.245602 0.395513 0.232269 0.026 Uiso 1 1 calc R U . . .
C4 C 0.0723(8) 0.3894(3) -0.0021(5) 0.0259(11) Uani 1 1 d . . . . .
H4 H 0.084852 0.369368 -0.089571 0.031 Uiso 1 1 calc R U . . .
C5 C 0.2273(7) 0.4325(3) 0.0616(5) 0.0238(10) Uani 1 1 d . . . . .
H5 H 0.348633 0.441462 0.017182 0.029 Uiso 1 1 calc R U . . .
C3 C -0.1027(8) 0.3757(3) 0.0640(5) 0.0257(11) Uani 1 1 d . . . . .
H3 H -0.210602 0.345359 0.021721 0.031 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N8 1.916(4) . ?
Cu1 O18 1.925(3) . ?
Cu1 O17 1.944(3) . ?
Cu1 O17 1.974(3) 3_566 ?
Cu1 Cu1 2.9991(10) 3_566 ?
O17 C1 1.348(5) . ?
O19 C12 1.354(5) . ?
O18 C10 1.290(5) . ?
N9 C10 1.324(6) . ?
N9 N8 1.390(5) . ?
N9 H9 0.8800 . ?
N8 C7 1.287(6) . ?
C10 C11 1.468(6) . ?
C1 C2 1.397(7) . ?
C1 C6 1.428(6) . ?
C12 C13 1.386(7) . ?
C12 C11 1.412(6) . ?
C6 C5 1.391(6) . ?
C6 C7 1.445(6) . ?
C16 C15 1.378(7) . ?
C16 C11 1.393(6) . ?
C16 H16 0.9500 . ?
C7 H7 0.9500 . ?
C13 C14 1.387(7) . ?
C13 H13 0.9500 . ?
C15 C14 1.387(7) . ?
C15 H15 0.9500 . ?
C14 H14 0.9500 . ?
C2 C3 1.375(7) . ?
C2 H2 0.9500 . ?
C4 C5 1.371(7) . ?
C4 C3 1.384(7) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C3 H3 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
N8 Cu1 O18 81.56(14) . . ?
N8 Cu1 O17 93.47(14) . . ?
O18 Cu1 O17 174.83(13) . . ?
N8 Cu1 O17 168.52(15) . 3_566 ?
O18 Cu1 O17 105.05(13) . 3_566 ?
O17 Cu1 O17 80.09(13) . 3_566 ?
N8 Cu1 Cu1 133.18(11) . 3_566 ?
O18 Cu1 Cu1 144.72(9) . 3_566 ?
O17 Cu1 Cu1 40.41(9) . 3_566 ?
O17 Cu1 Cu1 39.68(9) 3_566 3_566 ?
C1 O17 Cu1 126.6(3) . . ?
C1 O17 Cu1 133.4(3) . 3_566 ?
Cu1 O17 Cu1 99.91(13) . 3_566 ?
C10 O18 Cu1 111.2(3) . . ?
C10 N9 N8 109.8(3) . . ?
C10 N9 H9 125.1 . . ?
N8 N9 H9 125.1 . . ?
C7 N8 N9 117.9(4) . . ?
C7 N8 Cu1 127.9(3) . . ?
N9 N8 Cu1 114.2(3) . . ?
O18 C10 N9 122.9(4) . . ?
O18 C10 C11 118.4(4) . . ?
N9 C10 C11 118.7(4) . . ?
O17 C1 C2 119.4(4) . . ?
O17 C1 C6 122.8(4) . . ?
C2 C1 C6 117.8(4) . . ?
O19 C12 C13 117.6(4) . . ?
O19 C12 C11 122.3(4) . . ?
C13 C12 C11 120.1(4) . . ?
C5 C6 C1 118.6(4) . . ?
C5 C6 C7 117.2(4) . . ?
C1 C6 C7 124.2(4) . . ?
C15 C16 C11 121.7(4) . . ?
C15 C16 H16 119.2 . . ?
C11 C16 H16 119.2 . . ?
N8 C7 C6 124.7(4) . . ?
N8 C7 H7 117.6 . . ?
C6 C7 H7 117.6 . . ?
C16 C11 C12 118.4(4) . . ?
C16 C11 C10 119.8(4) . . ?
C12 C11 C10 121.8(4) . . ?
C12 C13 C14 119.9(4) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C16 C15 C14 119.2(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C14 C13 120.7(4) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C3 C2 C1 121.5(4) . . ?
C3 C2 H2 119.3 . . ?
C1 C2 H2 119.3 . . ?
C5 C4 C3 118.5(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C4 C5 C6 122.6(4) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?

_refine_diff_density_max         1.231
_refine_diff_density_min         -0.761
_refine_diff_density_rms         0.130






