# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_d20140
_database_code_depnum_ccdc_archive 'CCDC 1914195'
loop_
_audit_author_name
_audit_author_address
'Ting-Shen Kuo'
;Department of Chemistry, National Taiwan Normal University
Taiwan
;
_audit_update_record             
;
2019-05-06 deposited with the CCDC.	2019-08-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        TKU-1
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cu N4 O6'
_chemical_formula_sum            'C14 H14 Cu N4 O6'
_chemical_formula_weight         397.83

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'

_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                   6.000(2)
_cell_length_b                   7.988(3)
_cell_length_c                   8.967(4)
_cell_angle_alpha                75.720(14)
_cell_angle_beta                 76.573(14)
_cell_angle_gamma                88.048(12)
_cell_volume                     405.0(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    5015
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      25.07

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.631
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             203
_exptl_absorpt_coefficient_mu    1.388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8736
_exptl_absorpt_correction_T_max  0.9728
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8086
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.63
_diffrn_reflns_theta_max         25.03
_reflns_number_total             1416
_reflns_number_gt                1361
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2005)'

_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)+(0.0240P)²+0.2658P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1416
_refine_ls_number_parameters     117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0605
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
C1 C 0.3848(3) 0.6515(2) 0.0382(2) 0.0164(4) Uani 1 1 d . . .
C2 C 0.2665(3) 0.4926(2) 0.0950(2) 0.0176(4) Uani 1 1 d . . .
C3 C 0.0340(3) 0.4850(2) 0.1842(2) 0.0201(4) Uani 1 1 d . . .
C4 C 0.3646(3) 0.3395(2) 0.0570(2) 0.0171(4) Uani 1 1 d . . .
C5 C 0.7622(3) 0.9116(3) 0.2433(2) 0.0218(4) Uani 1 1 d . . .
H5 H 0.8917 0.9603 0.1623 0.026 Uiso 1 1 calc R . .
C6 C 1.0223(4) 0.8154(3) 0.4159(3) 0.0343(5) Uani 1 1 d . . .
H6A H 1.0657 0.6945 0.4255 0.051 Uiso 1 1 calc R . .
H6B H 1.0219 0.8473 0.5148 0.051 Uiso 1 1 calc R . .
H6C H 1.1326 0.8899 0.3287 0.051 Uiso 1 1 calc R . .
C7 C 0.6039(4) 0.7509(4) 0.5108(3) 0.0481(7) Uani 1 1 d . . .
H7A H 0.4643 0.7578 0.4709 0.072 Uiso 1 1 calc R . .
H7B H 0.5801 0.8073 0.5985 0.072 Uiso 1 1 calc R . .
H7C H 0.6400 0.6293 0.5482 0.072 Uiso 1 1 calc R . .
Cu1 Cu 0.5000 1.0000 0.0000 0.01648(13) Uani 1 2 d S . .
N1 N -0.1512(3) 0.4797(3) 0.2570(2) 0.0338(5) Uani 1 1 d . . .
N2 N 0.7935(3) 0.8373(2) 0.3844(2) 0.0235(4) Uani 1 1 d . . .
O1 O 0.2966(2) 0.79182(17) 0.05889(16) 0.0206(3) Uani 1 1 d . . .
O2 O 0.2621(2) 0.19801(17) 0.09632(17) 0.0228(3) Uani 1 1 d . . .
O3 O 0.5695(2) 0.92157(18) 0.21034(16) 0.0244(3) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0203(10) 0.0155(10) 0.0146(10) -0.0038(8) -0.0064(8) 0.0004(7)
C2 0.0193(10) 0.0157(10) 0.0177(10) -0.0037(8) -0.0044(7) -0.0005(7)
C3 0.0253(11) 0.0149(10) 0.0198(10) -0.0026(8) -0.0060(9) -0.0022(8)
C4 0.0215(10) 0.0148(10) 0.0153(10) -0.0015(8) -0.0067(8) -0.0014(7)
C5 0.0229(11) 0.0219(11) 0.0205(11) -0.0057(8) -0.0042(8) -0.0002(8)
C6 0.0275(12) 0.0482(15) 0.0305(13) -0.0097(11) -0.0139(10) 0.0061(10)
C7 0.0336(14) 0.070(2) 0.0274(13) 0.0125(13) -0.0054(11) -0.0083(13)
Cu1 0.0206(2) 0.01033(18) 0.0189(2) -0.00284(13) -0.00595(13) -0.00008(12)
N1 0.0274(11) 0.0364(11) 0.0327(11) -0.0060(9) 0.0002(9) -0.0008(8)
N2 0.0201(9) 0.0287(10) 0.0205(9) -0.0037(7) -0.0049(7) 0.0006(7)
O1 0.0222(7) 0.0132(7) 0.0262(8) -0.0066(6) -0.0032(6) 0.0014(5)
O2 0.0230(7) 0.0128(7) 0.0299(8) -0.0040(6) -0.0018(6) -0.0037(5)
O3 0.0224(7) 0.0280(8) 0.0219(8) -0.0016(6) -0.0081(6) 0.0002(6)

_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
C1 O1 1.260(2) . ?
C1 C2 1.396(3) . ?
C1 C4 1.542(3) 2_665 ?
C2 C4 1.422(3) . ?
C2 C3 1.433(3) . ?
C3 N1 1.148(3) . ?
C4 O2 1.237(2) . ?
C4 C1 1.542(3) 2_665 ?
C5 O3 1.253(2) . ?
C5 N2 1.311(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.461(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N2 1.458(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
Cu1 O3 1.9719(16) . ?
Cu1 O3 1.9719(16) 2_675 ?
Cu1 O1 1.9848(14) 2_675 ?
Cu1 O1 1.9848(14) . ?
Cu1 O2 2.2877(15) 1_565 ?
Cu1 O2 2.2877(15) 2_665 ?
O2 Cu1 2.2877(15) 1_545 ?

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 C1 C2 123.38(17) . . ?
O1 C1 C4 116.96(16) . 2_665 ?
C2 C1 C4 119.65(17) . 2_665 ?
C1 C2 C4 121.75(18) . . ?
C1 C2 C3 119.35(17) . . ?
C4 C2 C3 118.75(17) . . ?
N1 C3 C2 179.2(2) . . ?
O2 C4 C2 124.19(18) . . ?
O2 C4 C1 117.40(17) . 2_665 ?
C2 C4 C1 118.41(17) . 2_665 ?
O3 C5 N2 123.14(19) . . ?
O3 C5 H5 118.4 . . ?
N2 C5 H5 118.4 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O3 Cu1 O3 180.000(1) . 2_675 ?
O3 Cu1 O1 92.82(6) . 2_675 ?
O3 Cu1 O1 87.18(6) 2_675 2_675 ?
O3 Cu1 O1 87.18(6) . . ?
O3 Cu1 O1 92.82(6) 2_675 . ?
O1 Cu1 O1 180.0 2_675 . ?
O3 Cu1 O2 88.02(6) . 1_565 ?
O3 Cu1 O2 91.98(6) 2_675 1_565 ?
O1 Cu1 O2 77.47(6) 2_675 1_565 ?
O1 Cu1 O2 102.53(6) . 1_565 ?
O3 Cu1 O2 91.98(6) . 2_665 ?
O3 Cu1 O2 88.02(6) 2_675 2_665 ?
O1 Cu1 O2 102.53(6) 2_675 2_665 ?
O1 Cu1 O2 77.47(6) . 2_665 ?
O2 Cu1 O2 180.0 1_565 2_665 ?
C5 N2 C7 120.97(18) . . ?
C5 N2 C6 121.81(18) . . ?
C7 N2 C6 116.67(18) . . ?
C1 O1 Cu1 118.28(12) . . ?
C4 O2 Cu1 109.11(12) . 1_545 ?
C5 O3 Cu1 127.84(13) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 'Solvothermal reaction'
