# 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_CrystalClear
_database_code_depnum_ccdc_archive 'CCDC 1978140'
loop_
_audit_author_name
_audit_author_address
'yoshinobu kamakura'
;Kwansei Gakuin University
Japan
;
_audit_update_record             
;
2020-01-16 deposited with the CCDC.	2020-07-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 Cu N2 O4'
_chemical_formula_weight         383.84

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.111(2)
_cell_length_b                   11.154(2)
_cell_length_c                   15.896(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.510(9)
_cell_angle_gamma                90
_cell_volume                     1735.5(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    2233
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Platelet
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             780
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.282
_shelx_estimated_absorpt_T_min   0.861
_shelx_estimated_absorpt_T_max   0.975
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19670
_diffrn_reflns_av_unetI/netI     0.1644
_diffrn_reflns_av_R_equivalents  0.2131
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.081
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3977
_reflns_number_gt                1961
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1188P)²] 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         3977
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1937
_refine_ls_R_factor_gt           0.0918
_refine_ls_wR_factor_ref         0.2758
_refine_ls_wR_factor_gt          0.1978
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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_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 -0.13049(10) 0.04027(8) 0.58734(7) 0.0254(3) Uani 1 1 d . . . . .
O002 O 0.0667(6) 0.0536(5) 0.6468(4) 0.0296(14) Uani 1 1 d . . . . .
O003 O 0.6720(6) 0.0447(5) 0.5910(4) 0.0332(14) Uani 1 1 d . . . . .
O6 O 0.1714(6) -0.0383(6) 0.5571(4) 0.0335(14) Uani 1 1 d . . . . .
O005 O 0.7915(6) 0.0698(7) 0.7280(4) 0.0489(19) Uani 1 1 d . . . . .
N006 N -0.1343(7) 0.2225(6) 0.5794(5) 0.0282(16) Uani 1 1 d . . . . .
N007 N -0.1346(7) 0.8583(5) 0.5853(4) 0.0240(15) Uani 1 1 d . . . . .
C008 C -0.1390(9) 0.6067(7) 0.5747(5) 0.0255(19) Uani 1 1 d . . . . .
C009 C -0.1405(9) 0.4744(7) 0.5750(6) 0.032(2) Uani 1 1 d . . . . .
C00A C 0.4265(8) 0.0466(7) 0.6494(6) 0.0271(18) Uani 1 1 d . . . . .
H1 H 0.4234 -0.0035 0.6006 0.033 Uiso 1 1 calc R U . . .
C00B C 0.5507(9) 0.0943(10) 0.6960(6) 0.039(2) Uani 1 1 d . . . . .
C00C C -0.2497(10) 0.6772(8) 0.5330(6) 0.040(2) Uani 1 1 d . . . . .
H2 H -0.3293 0.6398 0.4984 0.048 Uiso 1 1 calc R U . . .
C00D C -0.2458(9) 0.7998(8) 0.5411(6) 0.035(2) Uani 1 1 d . . . . .
H3 H -0.3250 0.8447 0.5143 0.042 Uiso 1 1 calc R U . . .
C00E C 0.6809(9) 0.0637(8) 0.6718(6) 0.032(2) Uani 1 1 d . . . . .
C00F C -0.0245(9) 0.6691(8) 0.6225(6) 0.035(2) Uani 1 1 d . . . . .
H4 H 0.0547 0.6269 0.6529 0.042 Uiso 1 1 calc R U . . .
C00G C 0.1715(8) 0.0246(7) 0.6205(6) 0.0271(19) Uani 1 1 d . . . . .
C00H C -0.2170(11) 0.2835(9) 0.5135(7) 0.048(3) Uani 1 1 d . . . . .
H5 H -0.2751 0.2388 0.4681 0.057 Uiso 1 1 calc R U . . .
C00I C -0.0279(9) 0.7924(7) 0.6250(6) 0.029(2) Uani 1 1 d . . . . .
H6 H 0.0512 0.8330 0.6573 0.035 Uiso 1 1 calc R U . . .
C00J C -0.2221(10) 0.4077(8) 0.5081(7) 0.046(3) Uani 1 1 d . . . . .
H7 H -0.2805 0.4463 0.4595 0.055 Uiso 1 1 calc R U . . .
C00K C 0.3070(9) 0.0724(7) 0.6742(6) 0.028(2) Uani 1 1 d . . . . .
C00L C -0.0587(11) 0.4100(9) 0.6421(7) 0.052(3) Uani 1 1 d . . . . .
H8 H -0.0013 0.4524 0.6891 0.063 Uiso 1 1 calc R U . . .
C00M C 0.5546(11) 0.1665(12) 0.7683(7) 0.070(4) Uani 1 1 d . . . . .
H9 H 0.6396 0.1967 0.8014 0.084 Uiso 1 1 calc R U . . .
C00N C 0.3122(10) 0.1462(12) 0.7450(7) 0.065(4) Uani 1 1 d . . . . .
H10 H 0.2307 0.1644 0.7619 0.078 Uiso 1 1 calc R U . . .
C00O C -0.0569(12) 0.2893(9) 0.6438(7) 0.054(3) Uani 1 1 d . . . . .
H11 H 0.0011 0.2499 0.6921 0.064 Uiso 1 1 calc R U . . .
C00P C 0.4370(11) 0.1941(15) 0.7918(9) 0.097(6) Uani 1 1 d . . . . .
H12 H 0.4400 0.2457 0.8398 0.116 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
Cu01 O002 1.987(6) . ?
Cu01 O003 2.012(6) 1_455 ?
Cu01 N007 2.030(6) 1_545 ?
Cu01 N006 2.036(7) . ?
Cu01 O6 2.228(6) 3_556 ?
O002 C00G 1.275(10) . ?
O003 C00E 1.284(11) . ?
O003 Cu01 2.012(6) 1_655 ?
O6 C00G 1.228(10) . ?
O6 Cu01 2.228(6) 3_556 ?
O005 C00E 1.246(10) . ?
N006 C00O 1.347(11) . ?
N006 C00H 1.349(11) . ?
N007 C00I 1.327(10) . ?
N007 C00D 1.338(10) . ?
N007 Cu01 2.030(6) 1_565 ?
C008 C00C 1.392(12) . ?
C008 C00F 1.401(11) . ?
C008 C009 1.476(10) . ?
C009 C00L 1.377(12) . ?
C009 C00J 1.388(12) . ?
C00A C00K 1.392(11) . ?
C00A C00B 1.394(11) . ?
C00A H1 0.9500 . ?
C00B C00M 1.396(14) . ?
C00B C00E 1.500(12) . ?
C00C C00D 1.373(12) . ?
C00C H2 0.9500 . ?
C00D H3 0.9500 . ?
C00F C00I 1.376(12) . ?
C00F H4 0.9500 . ?
C00G C00K 1.518(12) . ?
C00H C00J 1.388(13) . ?
C00H H5 0.9500 . ?
C00I H6 0.9500 . ?
C00J H7 0.9500 . ?
C00K C00N 1.385(12) . ?
C00L C00O 1.346(13) . ?
C00L H8 0.9500 . ?
C00M C00P 1.368(15) . ?
C00M H9 0.9500 . ?
C00N C00P 1.400(13) . ?
C00N H10 0.9500 . ?
C00O H11 0.9500 . ?
C00P H12 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
O002 Cu01 O003 150.4(3) . 1_455 ?
O002 Cu01 N007 95.5(3) . 1_545 ?
O003 Cu01 N007 90.5(3) 1_455 1_545 ?
O002 Cu01 N006 87.5(3) . . ?
O003 Cu01 N006 88.5(3) 1_455 . ?
N007 Cu01 N006 175.5(3) 1_545 . ?
O002 Cu01 O6 113.3(2) . 3_556 ?
O003 Cu01 O6 95.8(2) 1_455 3_556 ?
N007 Cu01 O6 88.6(3) 1_545 3_556 ?
N006 Cu01 O6 87.1(3) . 3_556 ?
C00G O002 Cu01 130.0(6) . . ?
C00E O003 Cu01 102.2(5) . 1_655 ?
C00G O6 Cu01 144.4(6) . 3_556 ?
C00O N006 C00H 116.1(8) . . ?
C00O N006 Cu01 120.4(6) . . ?
C00H N006 Cu01 123.4(6) . . ?
C00I N007 C00D 117.1(7) . . ?
C00I N007 Cu01 122.4(6) . 1_565 ?
C00D N007 Cu01 120.5(6) . 1_565 ?
C00C C008 C00F 115.7(7) . . ?
C00C C008 C009 123.9(8) . . ?
C00F C008 C009 120.2(8) . . ?
C00L C009 C00J 116.1(8) . . ?
C00L C009 C008 121.3(8) . . ?
C00J C009 C008 122.6(8) . . ?
C00K C00A C00B 120.0(8) . . ?
C00K C00A H1 120.0 . . ?
C00B C00A H1 120.0 . . ?
C00A C00B C00M 119.6(9) . . ?
C00A C00B C00E 120.6(8) . . ?
C00M C00B C00E 119.8(8) . . ?
C00D C00C C008 121.2(8) . . ?
C00D C00C H2 119.4 . . ?
C008 C00C H2 119.4 . . ?
N007 C00D C00C 122.4(8) . . ?
N007 C00D H3 118.8 . . ?
C00C C00D H3 118.8 . . ?
O005 C00E O003 123.5(8) . . ?
O005 C00E C00B 119.5(8) . . ?
O003 C00E C00B 116.7(8) . . ?
C00I C00F C008 119.2(8) . . ?
C00I C00F H4 120.4 . . ?
C008 C00F H4 120.4 . . ?
O6 C00G O002 125.8(8) . . ?
O6 C00G C00K 118.6(7) . . ?
O002 C00G C00K 115.7(8) . . ?
N006 C00H C00J 123.9(9) . . ?
N006 C00H H5 118.1 . . ?
C00J C00H H5 118.1 . . ?
N007 C00I C00F 124.3(8) . . ?
N007 C00I H6 117.8 . . ?
C00F C00I H6 117.8 . . ?
C009 C00J C00H 118.8(9) . . ?
C009 C00J H7 120.6 . . ?
C00H C00J H7 120.6 . . ?
C00N C00K C00A 119.7(8) . . ?
C00N C00K C00G 120.7(8) . . ?
C00A C00K C00G 119.5(7) . . ?
C00O C00L C009 122.7(9) . . ?
C00O C00L H8 118.7 . . ?
C009 C00L H8 118.7 . . ?
C00P C00M C00B 120.6(10) . . ?
C00P C00M H9 119.7 . . ?
C00B C00M H9 119.7 . . ?
C00K C00N C00P 120.3(9) . . ?
C00K C00N H10 119.9 . . ?
C00P C00N H10 119.9 . . ?
C00L C00O N006 122.4(9) . . ?
C00L C00O H11 118.8 . . ?
N006 C00O H11 118.8 . . ?
C00M C00P C00N 119.9(10) . . ?
C00M C00P H12 120.1 . . ?
C00N C00P H12 120.1 . . ?

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
C00C C008 C009 C00L -152.5(10) . . . . ?
C00F C008 C009 C00L 23.6(14) . . . . ?
C00C C008 C009 C00J 28.3(14) . . . . ?
C00F C008 C009 C00J -155.6(9) . . . . ?
C00K C00A C00B C00M 0.9(16) . . . . ?
C00K C00A C00B C00E 177.9(8) . . . . ?
C00F C008 C00C C00D -1.7(13) . . . . ?
C009 C008 C00C C00D 174.5(9) . . . . ?
C00I N007 C00D C00C -2.8(13) . . . . ?
Cu01 N007 C00D C00C 175.4(7) 1_565 . . . ?
C008 C00C C00D N007 3.4(15) . . . . ?
Cu01 O003 C00E O005 -3.1(10) 1_655 . . . ?
Cu01 O003 C00E C00B 169.4(7) 1_655 . . . ?
C00A C00B C00E O005 -155.0(9) . . . . ?
C00M C00B C00E O005 22.0(15) . . . . ?
C00A C00B C00E O003 32.2(13) . . . . ?
C00M C00B C00E O003 -150.8(10) . . . . ?
C00C C008 C00F C00I -0.2(13) . . . . ?
C009 C008 C00F C00I -176.6(8) . . . . ?
Cu01 O6 C00G O002 79.1(12) 3_556 . . . ?
Cu01 O6 C00G C00K -101.6(10) 3_556 . . . ?
Cu01 O002 C00G O6 -13.9(12) . . . . ?
Cu01 O002 C00G C00K 166.8(5) . . . . ?
C00O N006 C00H C00J 2.1(15) . . . . ?
Cu01 N006 C00H C00J 178.8(8) . . . . ?
C00D N007 C00I C00F 0.8(13) . . . . ?
Cu01 N007 C00I C00F -177.4(7) 1_565 . . . ?
C008 C00F C00I N007 0.7(14) . . . . ?
C00L C009 C00J C00H 0.6(15) . . . . ?
C008 C009 C00J C00H 179.8(10) . . . . ?
N006 C00H C00J C009 -1.6(17) . . . . ?
C00B C00A C00K C00N 0.4(15) . . . . ?
C00B C00A C00K C00G 177.2(8) . . . . ?
O6 C00G C00K C00N 178.3(10) . . . . ?
O002 C00G C00K C00N -2.3(13) . . . . ?
O6 C00G C00K C00A 1.6(12) . . . . ?
O002 C00G C00K C00A -179.1(7) . . . . ?
C00J C009 C00L C00O -0.1(17) . . . . ?
C008 C009 C00L C00O -179.3(11) . . . . ?
C00A C00B C00M C00P -2(2) . . . . ?
C00E C00B C00M C00P -179.3(12) . . . . ?
C00A C00K C00N C00P -0.4(19) . . . . ?
C00G C00K C00N C00P -177.2(12) . . . . ?
C009 C00L C00O N006 0.6(19) . . . . ?
C00H N006 C00O C00L -1.5(16) . . . . ?
Cu01 N006 C00O C00L -178.4(9) . . . . ?
C00B C00M C00P C00N 2(2) . . . . ?
C00K C00N C00P C00M -1(2) . . . . ?

_refine_diff_density_max         0.853
_refine_diff_density_min         -1.259
_refine_diff_density_rms         0.258

