# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1865055'
loop_
_audit_author_name
_audit_author_address
'Ji-Jun JIANG'
;Lehn Institute of Functional Materials, Sun Yat-Sen University
China
;
_audit_update_record             
;
2018-08-31 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2014-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13.81 H7.9 Cu N2 O5, 3.5(O), 0.5(C O)'
_chemical_formula_sum            'C14.31 H7.91 Cu N2 O9'
_chemical_formula_weight         415.38
_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 0.0180 0.0090 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9650 0.5890 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0310 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0490 0.0320 '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'

_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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'-x, -x+y, -z+1/2'
'x-y, -y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'x, x-y, z-1/2'
'-x+y, y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'

_cell_length_a                   18.3138(2)
_cell_length_b                   18.3138(2)
_cell_length_c                   69.7479(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     20259.0(6)
_cell_formula_units_Z            36
_cell_measurement_reflns_used    1219
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      62.3068
_cell_measurement_theta_min      3.0217
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.721
_exptl_absorpt_coefficient_mu    1.749
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             7514
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.876
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       79
_diffrn_reflns_limit_l_min       -73
_diffrn_reflns_number            17937
_diffrn_reflns_point_group_measured_fraction_full 0.876
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         62.446
_diffrn_reflns_theta_min         3.061
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.876
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3338
_reflns_number_total             3570
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.059
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.169
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0787
_refine_ls_restrained_S_all      1.118
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.1556P)²+115.6297P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2366
_refine_ls_wR_factor_ref         0.2405
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained planarity
 N4, C5B, C4B, C3B, C2A, C1B, C6B
 with sigma of 0.02
 N2, C6B, C4B, O1B
 with sigma of 0.02
 C7, N2, C6A, O1A, C4A
 with sigma of 0.02
 C4A, C6A, C5A, N4, C1B, C2B, C3A
 with sigma of 0.02
 C5B, C4B, C3B, C2A, C1B, N4, C6B
 with sigma of 0.02
 C7, N2, C6B, C4B, O1B
 with sigma of 0.02
3. Others
 Fixed Sof: O1A(0.5) O1B(0.5) O3W(0.5) H2a(0.5) H2b(0.5) H1Ba(0.5) C2A(0.5)
 H2Aa(0.5) H2Ba(0.5) C3A(0.5) H3A(0.5) C3B(0.5) H3B(0.5) C4A(0.5) C4B(0.5)
 C5A(0.5) H5A(0.5) C5B(0.5) H5B(0.5) C6A(0.5) C6B(0.5) C1(0.5) O1(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N2(H2a), N2(H2b), C1B(H1Ba), C1B(H1B), C2A(H2Aa), C2B(H2Ba), C3A(H3A),
 C3B(H3B), C5A(H5A), C5B(H5B), C8(H8), C10(H10), C12(H12)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 0.38355(3) 0.21116(4) -0.06809(2) 0.0347(3) Uani 1 1 d . . . . .
O1A O 0.3862(7) 0.1132(5) 0.00848(11) 0.083(3) Uani 0.5 1 d . . P A 1
O1B O 0.4404(11) 0.3436(11) 0.02046(19) 0.146(6) Uani 0.5 1 d . . P B 2
O1W O 0.643(3) 0.412(3) 0.0329(5) 0.60(2) Uiso 1 1 d . . . . .
O2W O 0.050(2) 0.593(2) 0.0501(4) 0.53(2) Uiso 1 1 d . . . . .
O3 O 0.2099(3) 0.3094(2) 0.05768(5) 0.0619(11) Uani 1 1 d . . . . .
O3W O 0.4113(7) 0.3932(7) 0.01473(15) 0.086(3) Uiso 0.5 1 d . . P C 1
O4 O 0.1708(3) 0.2266(2) 0.08350(6) 0.0638(11) Uani 1 1 d . . . . .
O4W O 0.552(2) 0.505(2) 0.0562(5) 0.56(2) Uiso 1 1 d . . . . .
O5 O 0.2477(2) -0.0561(2) 0.05885(5) 0.0497(8) Uani 1 1 d . . . . .
O6 O 0.2024(2) -0.0181(2) 0.08459(5) 0.0498(8) Uani 1 1 d . . . . .
N2 N 0.3761(3) 0.2152(4) 0.01846(9) 0.102(3) Uani 1 1 d . . . . .
H2A H 0.3910 0.2680 0.0160 0.123 Uiso 0.5 1 calc R . P D 1
H2B H 0.3663 0.1692 0.0123 0.123 Uiso 0.5 1 calc R . P D 2
N4 N 0.4601(2) 0.2579(2) -0.04250(5) 0.0409(9) Uani 1 1 d . . . . .
C1B C 0.5322(3) 0.3305(3) -0.04218(7) 0.0536(13) Uani 1 1 d . . . . .
H1BA H 0.5592 0.3514 -0.0542 0.064 Uiso 0.5 1 calc R . P E 2
H1B H 0.5590 0.3599 -0.0536 0.064 Uiso 0.40(11) 1 calc R . . E 1
C2A C 0.5713(11) 0.3778(12) -0.0268(3) 0.065(6) Uani 0.5 1 d . . P B 2
H2AA H 0.6255 0.4262 -0.0282 0.078 Uiso 0.5 1 calc R . P B 2
C2B C 0.568(2) 0.363(2) -0.0234(5) 0.040(8) Uiso 0.31(3) 1 d . . . A 1
H2BA H 0.6193 0.4150 -0.0226 0.049 Uiso 0.5 1 calc R . P A 1
C3A C 0.5314(10) 0.3214(9) -0.0070(2) 0.046(3) Uani 0.5 1 d . . P A 1
H3A H 0.5554 0.3445 0.0051 0.056 Uiso 0.5 1 calc R . P A 1
C3B C 0.5385(13) 0.3597(12) -0.0108(4) 0.086(6) Uani 0.5 1 d . . P B 2
H3B H 0.5666 0.3960 -0.0003 0.103 Uiso 0.5 1 calc R . P B 2
C4A C 0.4561(5) 0.2426(5) -0.00849(12) 0.0318(18) Uani 0.5 1 d . . P A 1
C4B C 0.4685(10) 0.2941(10) -0.00813(16) 0.073(4) Uani 0.5 1 d . . P B 2
C5A C 0.4212(7) 0.2108(8) -0.0267(3) 0.037(3) Uani 0.5 1 d . . P A 1
H5A H 0.3715 0.1574 -0.0280 0.044 Uiso 0.5 1 calc R . P A 1
C5B C 0.4298(10) 0.2429(9) -0.0249(4) 0.071(6) Uani 0.5 1 d . . P B 2
H5B H 0.3769 0.1932 -0.0231 0.085 Uiso 0.5 1 calc R . P B 2
C6A C 0.4041(6) 0.1845(6) 0.00714(13) 0.054(3) Uani 0.5 1 d . . P A 1
C6B C 0.4197(9) 0.2631(14) 0.0094(2) 0.180(15) Uani 0.5 1 d . . P B 2
C7 C 0.3245(4) 0.1821(4) 0.03470(9) 0.0711(18) Uani 1 1 d . . . . .
C8 C 0.2897(4) 0.2279(4) 0.04241(9) 0.0715(18) Uani 1 1 d . . . . .
H8 H 0.3002 0.2790 0.0365 0.086 Uiso 1 1 calc R . . . .
C9 C 0.2396(4) 0.1993(3) 0.05869(8) 0.0567(13) Uani 1 1 d . . . . .
C10 C 0.2232(3) 0.1234(3) 0.06707(7) 0.0486(11) Uani 1 1 d . . . . .
H10 H 0.1898 0.1040 0.0784 0.058 Uiso 1 1 calc R . . . .
C11 C 0.2551(3) 0.0765(3) 0.05908(7) 0.0475(11) Uani 1 1 d . . . . .
C12 C 0.3064(4) 0.1053(4) 0.04274(8) 0.0594(14) Uani 1 1 d . . . . .
H12 H 0.3285 0.0730 0.0372 0.071 Uiso 1 1 calc R . . . .
C13 C 0.2043(3) 0.2487(3) 0.06730(7) 0.0499(12) Uani 1 1 d . . . . .
C14 C 0.2335(3) -0.0061(3) 0.06805(6) 0.0399(10) Uani 1 1 d . . . . .
C1 C 0.4425(14) 0.4794(15) 0.0023(3) 0.118(6) Uiso 0.5 1 d . . P C 1
O1 O 0.363(2) 0.063(2) -0.0026(5) 0.282(15) Uiso 0.5 1 d . . P F 2


_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 2.6570(11) 11_554 ?
Cu1 O3 1.944(3) 20 ?
Cu1 O4 1.973(4) 28 ?
Cu1 O5 1.993(3) 21 ?
Cu1 O6 1.927(3) 30 ?
Cu1 N4 2.164(4) . ?
O1A C6A 1.179(12) . ?
O1B C6B 1.54(3) . ?
O3 Cu1 1.944(3) 21 ?
O3 C13 1.257(6) . ?
O3W C1 1.64(2) . ?
O4 Cu1 1.973(4) 34 ?
O4 C13 1.252(6) . ?
O5 Cu1 1.993(3) 20 ?
O5 C14 1.247(5) . ?
O6 Cu1 1.927(3) 36_545 ?
O6 C14 1.256(5) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N2 C6A 1.221(11) . ?
N2 C6B 1.05(2) . ?
N2 C7 1.403(8) . ?
N4 C1B 1.326(6) . ?
N4 C5A 1.36(2) . ?
N4 C5B 1.32(3) . ?
C1B H1BA 0.9500 . ?
C1B H1B 0.9500 . ?
C1B C2A 1.34(2) . ?
C1B C2B 1.45(4) . ?
C2A H2AA 0.9500 . ?
C2A C3B 1.23(3) . ?
C2B H2BA 0.9500 . ?
C2B C3A 1.35(4) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.416(18) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.26(3) . ?
C4A C5A 1.41(2) . ?
C4A C6A 1.488(14) . ?
C4B C5B 1.45(3) . ?
C4B C6B 1.45(2) . ?
C5A H5A 0.9500 . ?
C5B H5B 0.9500 . ?
C7 C8 1.390(8) . ?
C7 C12 1.392(7) . ?
C8 H8 0.9500 . ?
C8 C9 1.387(8) . ?
C9 C10 1.395(7) . ?
C9 C13 1.477(7) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(7) . ?
C11 C12 1.401(7) . ?
C11 C14 1.496(6) . ?
C12 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
O3 Cu1 Cu1 86.34(10) 20 11_554 ?
O3 Cu1 O4 88.4(2) 20 28 ?
O3 Cu1 O5 89.35(18) 20 21 ?
O3 Cu1 N4 94.70(14) 20 . ?
O4 Cu1 Cu1 81.14(10) 28 11_554 ?
O4 Cu1 O5 164.08(14) 28 21 ?
O4 Cu1 N4 103.63(14) 28 . ?
O5 Cu1 Cu1 82.99(9) 21 11_554 ?
O5 Cu1 N4 92.27(13) 21 . ?
O6 Cu1 Cu1 84.46(9) 30 11_554 ?
O6 Cu1 O3 170.76(14) 30 20 ?
O6 Cu1 O4 89.42(18) 30 28 ?
O6 Cu1 O5 90.29(16) 30 21 ?
O6 Cu1 N4 94.54(13) 30 . ?
N4 Cu1 Cu1 175.14(10) . 11_554 ?
C13 O3 Cu1 121.1(3) . 21 ?
C13 O4 Cu1 126.0(3) . 34 ?
C14 O5 Cu1 122.4(3) . 20 ?
C14 O6 Cu1 123.9(3) . 36_545 ?
C6A N2 H2A 114.0 . . ?
C6A N2 C7 132.1(7) . . ?
C6B N2 H2B 102.1 . . ?
C6B N2 C7 155.8(13) . . ?
C7 N2 H2A 114.0 . . ?
C7 N2 H2B 102.1 . . ?
C1B N4 Cu1 122.3(3) . . ?
C1B N4 C5A 124.5(6) . . ?
C5A N4 Cu1 112.7(6) . . ?
C5B N4 Cu1 124.3(7) . . ?
C5B N4 C1B 107.4(8) . . ?
N4 C1B H1BA 116.4 . . ?
N4 C1B H1B 121.8 . . ?
N4 C1B C2A 127.1(11) . . ?
N4 C1B C2B 116.4(15) . . ?
C2A C1B H1BA 116.4 . . ?
C2B C1B H1B 121.8 . . ?
C1B C2A H2AA 119.3 . . ?
C3B C2A C1B 121.4(18) . . ?
C3B C2A H2AA 119.3 . . ?
C1B C2B H2BA 118.7 . . ?
C3A C2B C1B 123(3) . . ?
C3A C2B H2BA 118.7 . . ?
C2B C3A H3A 121.0 . . ?
C2B C3A C4A 118(2) . . ?
C4A C3A H3A 121.0 . . ?
C2A C3B H3B 119.3 . . ?
C2A C3B C4B 121(2) . . ?
C4B C3B H3B 119.3 . . ?
C3A C4A C6A 128.7(9) . . ?
C5A C4A C3A 119.6(11) . . ?
C5A C4A C6A 111.7(9) . . ?
C3B C4B C5B 115.6(17) . . ?
C3B C4B C6B 129.4(17) . . ?
C5B C4B C6B 115.0(16) . . ?
N4 C5A C4A 118.8(9) . . ?
N4 C5A H5A 120.6 . . ?
C4A C5A H5A 120.6 . . ?
N4 C5B C4B 126.9(15) . . ?
N4 C5B H5B 116.5 . . ?
C4B C5B H5B 116.5 . . ?
O1A C6A N2 120.7(10) . . ?
O1A C6A C4A 125.0(8) . . ?
N2 C6A C4A 114.2(7) . . ?
N2 C6B O1B 102.5(15) . . ?
N2 C6B C4B 153.6(19) . . ?
C4B C6B O1B 103.9(14) . . ?
C8 C7 N2 117.7(5) . . ?
C8 C7 C12 120.2(5) . . ?
C12 C7 N2 122.0(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C10 119.4(5) . . ?
C8 C9 C13 120.8(4) . . ?
C10 C9 C13 119.8(5) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(5) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.5(4) . . ?
C10 C11 C14 118.8(4) . . ?
C12 C11 C14 120.7(4) . . ?
C7 C12 C11 119.0(5) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O3 C13 C9 117.2(4) . . ?
O4 C13 O3 125.3(5) . . ?
O4 C13 C9 117.5(4) . . ?
O5 C14 O6 125.9(4) . . ?
O5 C14 C11 118.7(4) . . ?
O6 C14 C11 115.4(4) . . ?

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 O3 C13 O4 4.4(8) 21 . . . ?
Cu1 O3 C13 C9 -176.1(4) 21 . . . ?
Cu1 O4 C13 O3 -2.5(9) 34 . . . ?
Cu1 O4 C13 C9 178.0(4) 34 . . . ?
Cu1 O5 C14 O6 6.7(7) 20 . . . ?
Cu1 O5 C14 C11 -173.7(3) 20 . . . ?
Cu1 O6 C14 O5 -5.4(7) 36_545 . . . ?
Cu1 O6 C14 C11 175.0(3) 36_545 . . . ?
Cu1 N4 C1B C2A 158.1(7) . . . . ?
Cu1 N4 C1B C2B 167.5(7) . . . . ?
Cu1 N4 C5A C4A -167.8(4) . . . . ?
Cu1 N4 C5B C4B -154.7(4) . . . . ?
N2 C7 C8 C9 -178.7(6) . . . . ?
N2 C7 C12 C11 179.4(5) . . . . ?
N4 C1B C2A C3B -5.7(12) . . . . ?
N4 C1B C2B C3A 0.8(13) . . . . ?
C1B N4 C5A C4A 4.2(9) . . . . ?
C1B N4 C5B C4B -1.8(4) . . . . ?
C1B C2A C3B C4B 3.1(10) . . . . ?
C1B C2B C3A C4A 1.6(14) . . . . ?
C2A C1B C2B C3A 146(7) . . . . ?
C2A C3B C4B C5B -0.6(5) . . . . ?
C2A C3B C4B C6B -179.0(7) . . . . ?
C2B C1B C2A C3B -45(6) . . . . ?
C2B C3A C4A C5A -1.2(10) . . . . ?
C2B C3A C4A C6A 179.3(6) . . . . ?
C3A C4A C5A N4 -1.5(6) . . . . ?
C3A C4A C6A O1A -123.6(9) . . . . ?
C3A C4A C6A N2 60.3(7) . . . . ?
C3B C4B C5B N4 0.0(3) . . . . ?
C3B C4B C6B O1B 31.7(8) . . . . ?
C3B C4B C6B N2 -152.0(10) . . . . ?
C5A N4 C1B C2A -13.1(9) . . . . ?
C5A N4 C1B C2B -3.7(10) . . . . ?
C5A N4 C5B C4B 139(2) . . . . ?
C5A C4A C6A O1A 56.9(8) . . . . ?
C5A C4A C6A N2 -119.2(6) . . . . ?
C5B N4 C1B C2A 4.6(8) . . . . ?
C5B N4 C1B C2B 14.0(7) . . . . ?
C5B N4 C5A C4A -43.0(17) . . . . ?
C5B C4B C6B O1B -146.7(7) . . . . ?
C5B C4B C6B N2 29.5(11) . . . . ?
C6A N2 C6B O1B -162.2(7) . . . . ?
C6A N2 C6B C4B 21.6(10) . . . . ?
C6A N2 C7 C8 -167.3(8) . . . . ?
C6A N2 C7 C12 11.1(9) . . . . ?
C6A C4A C5A N4 178.1(4) . . . . ?
C6B N2 C6A O1A 174.5(9) . . . . ?
C6B N2 C6A C4A -9.3(7) . . . . ?
C6B N2 C7 C8 32.2(12) . . . . ?
C6B N2 C7 C12 -149.3(11) . . . . ?
C6B C4B C5B N4 178.7(4) . . . . ?
C7 N2 C6A O1A 2.8(8) . . . . ?
C7 N2 C6A C4A 179.1(5) . . . . ?
C7 N2 C6B O1B 2.6(10) . . . . ?
C7 N2 C6B C4B -173.7(9) . . . . ?
C7 C8 C9 C10 -1.1(11) . . . . ?
C7 C8 C9 C13 178.2(6) . . . . ?
C8 C7 C12 C11 -2.2(11) . . . . ?
C8 C9 C10 C11 -1.2(9) . . . . ?
C8 C9 C13 O3 11.3(9) . . . . ?
C8 C9 C13 O4 -169.2(6) . . . . ?
C9 C10 C11 C12 1.8(9) . . . . ?
C9 C10 C11 C14 -177.7(5) . . . . ?
C10 C9 C13 O3 -169.4(6) . . . . ?
C10 C9 C13 O4 10.1(8) . . . . ?
C10 C11 C12 C7 -0.1(9) . . . . ?
C10 C11 C14 O5 165.8(5) . . . . ?
C10 C11 C14 O6 -14.6(7) . . . . ?
C12 C7 C8 C9 2.9(11) . . . . ?
C12 C11 C14 O5 -13.7(8) . . . . ?
C12 C11 C14 O6 165.9(5) . . . . ?
C13 C9 C10 C11 179.5(5) . . . . ?
C14 C11 C12 C7 179.4(5) . . . . ?


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.066 -0.062 -0.002 6963 2005 ' '
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1865056'
loop_
_audit_author_name
_audit_author_address
'Ji-Jun JIANG'
;Lehn Institute of Functional Materials, Sun Yat-Sen University
China
;
_audit_update_record             
;
2018-08-31 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2014-01-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.12.10 svn.r2850 for OlexSys, GUI svn.r4736)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H8 Cu N2 O5'
_chemical_formula_sum            'C14 H8 Cu N2 O5'
_chemical_formula_weight         347.76
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   17.993(3)
_cell_length_b                   17.993(3)
_cell_length_c                   69.267(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     19420(7)
_cell_formula_units_Z            36
_cell_measurement_reflns_used    563
_cell_measurement_temperature    435(2)
_cell_measurement_theta_max      59.1957
_cell_measurement_theta_min      2.8319
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.857
_exptl_absorpt_coefficient_mu    1.594
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             6300
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1102
_diffrn_reflns_av_unetI/netI     0.1027
_diffrn_reflns_Laue_measured_fraction_full 0.779
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       72
_diffrn_reflns_limit_l_min       -76
_diffrn_reflns_number            8927
_diffrn_reflns_point_group_measured_fraction_full 0.779
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         58.910
_diffrn_reflns_theta_min         3.110
_diffrn_ambient_temperature      435.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.779
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1589
_reflns_number_total             3058
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS-2013 (Sheldrick, 2008)'
_refine_diff_density_max         0.807
_refine_diff_density_min         -0.635
_refine_diff_density_rms         0.174
_refine_ls_extinction_coef       0.00013(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         3058
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1962
_refine_ls_R_factor_gt           0.1294
_refine_ls_restrained_S_all      1.162
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.2000P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3374
_refine_ls_wR_factor_ref         0.3791
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N1-C1 = C1-C2A = C2A-C3A = C3A-C4A = C4A-C5A = C5A-N1
 1.4 with sigma of 0.02
 N1-C1 = C1-C2B = C2B-C3B = C3B-C4B = C4B-C5B = C5B-N1
 1.4 with sigma of 0.02
3. Restrained planarity
 N2, C6B, O1B, C4B
 with sigma of 0.02
 C6A, C4A, O1A, N2
 with sigma of 0.02
 N1, C1, C2A, C3A, C4A, C5A
 with sigma of 0.02
 N1, C1, C2B, C3B, C4B, C5B
 with sigma of 0.02
4. Others
 Sof(C5B)=Sof(H5B)=1-FVAR(1)
 Sof(C5A)=Sof(H5A)=FVAR(1)
 Fixed Sof: O1A(0.5) O1B(0.5) H2B(0.5) H2A(0.5) H1A(0.5) H1B(0.5) C2A(0.5)
 H2AA(0.5) C3A(0.5) H3A(0.5) C3B(0.5) H3B(0.5) C4A(0.5) C4B(0.5) C6A(0.5)
 C6B(0.5) C2B(0.5) H2BA(0.5)
 Fixed Uiso: C2B(0.1)
5.a Aromatic/amide H refined with riding coordinates:
 N2(H2B), N2(H2A), C1(H1A), C1(H1B), C2A(H2AA), C3A(H3A), C3B(H3B), C5A(H5A),
 C5B(H5B), C8(H8), C10(H10), C12(H12), C2B(H2BA)
;
_atom_sites_solution_hydrogens   geom
_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
Cu1 Cu 1.14736(12) 1.38742(10) 0.06788(2) 0.0720(8) Uani 1 1 d . . . . .
O1A O 0.928(3) 1.626(3) 0.1504(8) 0.26(2) Uiso 0.5 1 d . . P A 1
O1B O 0.848(5) 1.394(5) 0.1463(9) 0.35(3) Uiso 0.5 1 d . . P B 2
O2 O 1.0608(6) 1.3678(5) 0.10760(12) 0.091(3) Uani 1 1 d . . . . .
O3 O 1.1076(6) 1.4515(5) 0.08150(11) 0.088(3) Uani 1 1 d . . . . .
O4 O 1.1852(7) 1.7493(6) 0.08536(13) 0.094(3) Uani 1 1 d . . . . .
O5 O 1.1450(7) 1.7954(6) 0.11047(12) 0.096(3) Uani 1 1 d . . . . .
N1 N 0.8676(6) 1.4960(7) 0.20898(11) 0.081(3) Uani 1 1 d D . . . .
N2 N 0.9715(10) 1.5366(9) 0.15269(18) 0.114(4) Uani 1 1 d . . . . .
H2B H 0.9945 1.5755 0.1615 0.137 Uiso 0.5 1 calc R . P C 2
H2A H 0.9726 1.4983 0.1599 0.137 Uiso 0.5 1 calc R . P C 1
C1 C 0.7911(8) 1.4942(10) 0.2109(2) 0.152(9) Uani 1 1 d D . . . .
H1A H 0.7605 1.4764 0.2224 0.183 Uiso 0.5 1 calc R . P D 1
H1B H 0.7702 1.5023 0.2225 0.183 Uiso 0.5 1 calc R . P D 2
C2A C 0.759(2) 1.5199(14) 0.1951(4) 0.137(14) Uiso 0.5 1 d D . P A 1
H2AA H 0.7072 1.5187 0.1965 0.164 Uiso 0.5 1 calc R . P A 1
C3A C 0.8025(16) 1.5467(17) 0.1778(6) 0.151(14) Uiso 0.5 1 d D . P A 1
H3A H 0.7811 1.5639 0.1676 0.181 Uiso 0.5 1 calc R . P A 1
C3B C 0.7757(18) 1.4663(16) 0.1756(5) 0.153(14) Uiso 0.5 1 d D . P B 2
H3B H 0.7426 1.4562 0.1645 0.184 Uiso 0.5 1 calc R . P B 2
C4A C 0.8792(13) 1.5467(13) 0.1764(3) 0.068(6) Uiso 0.5 1 d D . P A 1
C4B C 0.8545(15) 1.4696(15) 0.1750(3) 0.090(7) Uiso 0.5 1 d D . P B 2
C5A C 0.9089(11) 1.5224(12) 0.1921(2) 0.072(7) Uiso 0.64(5) 1 d D . P A 1
H5A H 0.9615 1.5247 0.1910 0.087 Uiso 0.64(5) 1 calc R . P A 1
C5B C 0.8989(14) 1.4841(13) 0.1920(2) 0.047(11) Uiso 0.36(5) 1 d D . P B 2
H5B H 0.9515 1.4859 0.1920 0.057 Uiso 0.36(5) 1 calc R . P A 2
C6A C 0.930(2) 1.566(2) 0.1592(6) 0.134(12) Uiso 0.5 1 d . . P A 1
C6B C 0.900(2) 1.473(2) 0.1569(5) 0.122(11) Uiso 0.5 1 d . . P B 2
C7 C 1.0206(11) 1.5532(11) 0.1347(2) 0.103(5) Uani 1 1 d . . . . .
C8 C 1.0253(10) 1.4880(9) 0.12569(18) 0.094(4) Uani 1 1 d . . . . .
H8 H 0.9980 1.4333 0.1310 0.113 Uiso 1 1 calc R . . . .
C9 C 1.0701(9) 1.5036(8) 0.10883(17) 0.078(3) Uani 1 1 d . . . . .
C10 C 1.1085(10) 1.5852(8) 0.10069(18) 0.085(4) Uani 1 1 d . . . . .
H10 H 1.1370 1.5950 0.0889 0.102 Uiso 1 1 calc R . . . .
C11 C 1.1052(10) 1.6512(9) 0.10968(18) 0.086(4) Uani 1 1 d . . . . .
C12 C 1.0613(12) 1.6349(11) 0.1270(2) 0.111(5) Uani 1 1 d . . . . .
H12 H 1.0591 1.6791 0.1335 0.133 Uiso 1 1 calc R . . . .
C13 C 1.1517(11) 1.7402(8) 0.10071(19) 0.091(4) Uani 1 1 d . . . . .
C14 C 1.0802(9) 1.4354(8) 0.09884(17) 0.077(3) Uani 1 1 d . . . . .
C2B C 0.7489(18) 1.4790(13) 0.1935(3) 0.100 Uiso 0.5 1 d D . P B 2
H2BA H 0.6962 1.4769 0.1938 0.120 Uiso 0.5 1 calc R . P B 2


_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 2.725(3) 17_674 ?
Cu1 O2 2.045(9) 17_674 ?
Cu1 O3 1.886(8) . ?
Cu1 O4 2.016(9) 2_875 ?
Cu1 O5 1.933(9) 18_754 ?
Cu1 N1 2.170(9) 28_775 ?
O1A C6A 1.26(6) . ?
O1B C6B 1.45(7) . ?
O2 Cu1 2.045(9) 17_674 ?
O2 C14 1.243(14) . ?
O3 C14 1.275(14) . ?
O4 Cu1 2.016(9) 3_685 ?
O4 C13 1.192(16) . ?
O5 Cu1 1.932(9) 18_764 ?
O5 C13 1.256(15) . ?
N1 Cu1 2.169(9) 34_775 ?
N1 C1 1.367(12) . ?
N1 C5A 1.336(15) . ?
N1 C5B 1.364(17) . ?
N2 C6A 1.20(5) . ?
N2 C6B 1.26(4) . ?
N2 C7 1.472(18) . ?
C1 C2A 1.415(19) . ?
C1 C2B 1.376(18) . ?
C2A C3A 1.379(19) . ?
C3A C4A 1.384(19) . ?
C3B C4B 1.390(19) . ?
C3B C2B 1.391(19) . ?
C4A C5A 1.379(17) . ?
C4A C6A 1.43(5) . ?
C4B C5B 1.374(18) . ?
C4B C6B 1.48(5) . ?
C7 C8 1.37(2) . ?
C7 C12 1.38(2) . ?
C8 C9 1.366(17) . ?
C9 C10 1.392(17) . ?
C9 C14 1.497(17) . ?
C10 C11 1.369(17) . ?
C11 C12 1.385(19) . ?
C11 C13 1.520(19) . ?

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 79.5(2) 17_674 17_674 ?
O2 Cu1 N1 92.7(4) 17_674 28_775 ?
O3 Cu1 Cu1 86.2(2) . 17_674 ?
O3 Cu1 O2 92.5(4) . 17_674 ?
O3 Cu1 O4 89.1(4) . 2_875 ?
O3 Cu1 O5 174.7(3) . 18_754 ?
O3 Cu1 N1 91.2(3) . 28_775 ?
O4 Cu1 Cu1 76.1(3) 2_875 17_674 ?
O4 Cu1 O2 155.3(4) 2_875 17_674 ?
O4 Cu1 N1 111.9(4) 2_875 28_775 ?
O5 Cu1 Cu1 88.8(3) 18_754 17_674 ?
O5 Cu1 O2 88.3(4) 18_754 17_674 ?
O5 Cu1 O4 87.9(4) 18_754 2_875 ?
O5 Cu1 N1 94.0(4) 18_754 28_775 ?
N1 Cu1 Cu1 171.6(3) 28_775 17_674 ?
C14 O2 Cu1 124.6(8) . 17_674 ?
C14 O3 Cu1 123.7(8) . . ?
C13 O4 Cu1 130.0(9) . 3_685 ?
C13 O5 Cu1 117.1(8) . 18_764 ?
C1 N1 Cu1 118.3(8) . 34_775 ?
C5A N1 Cu1 116.8(9) . 34_775 ?
C5A N1 C1 117.9(12) . . ?
C5B N1 Cu1 116.9(11) . 34_775 ?
C5B N1 C1 124.7(14) . . ?
C6A N2 C7 132(2) . . ?
C6B N2 C7 128(2) . . ?
N1 C1 C2A 119(2) . . ?
N1 C1 C2B 111.6(17) . . ?
C3A C2A C1 122(4) . . ?
C2A C3A C4A 117(4) . . ?
C4B C3B C2B 117(3) . . ?
C3A C4A C6A 125(3) . . ?
C5A C4A C3A 119(2) . . ?
C5A C4A C6A 116(2) . . ?
C3B C4B C6B 124(2) . . ?
C5B C4B C3B 118(3) . . ?
C5B C4B C6B 118(2) . . ?
N1 C5A C4A 124.7(17) . . ?
N1 C5B C4B 121(2) . . ?
O1A C6A C4A 109(4) . . ?
N2 C6A O1A 119(5) . . ?
N2 C6A C4A 132(4) . . ?
O1B C6B C4B 109(4) . . ?
N2 C6B O1B 130(4) . . ?
N2 C6B C4B 121(3) . . ?
C8 C7 N2 120.0(14) . . ?
C8 C7 C12 120.8(13) . . ?
C12 C7 N2 119.2(14) . . ?
C9 C8 C7 119.7(13) . . ?
C8 C9 C10 119.6(11) . . ?
C8 C9 C14 121.9(11) . . ?
C10 C9 C14 118.5(11) . . ?
C11 C10 C9 121.1(11) . . ?
C10 C11 C12 118.5(13) . . ?
C10 C11 C13 119.2(11) . . ?
C12 C11 C13 122.2(12) . . ?
C7 C12 C11 120.1(14) . . ?
O4 C13 O5 127.9(13) . . ?
O4 C13 C11 118.9(11) . . ?
O5 C13 C11 113.1(12) . . ?
O2 C14 O3 124.7(11) . . ?
O2 C14 C9 119.2(10) . . ?
O3 C14 C9 116.2(10) . . ?
C1 C2B C3B 128(3) . . ?


# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.066 -0.062 -0.002 6963 2005 ' '
####################################################################### 
# 
# 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 1865058'
loop_
_audit_author_name
_audit_author_address
'Ji-Jun JIANG'
;Lehn Institute of Functional Materials, Sun Yat-Sen University
China
;
_audit_update_record             
;
2018-08-31 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2018-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cu N2 O5, O'
_chemical_formula_sum            'C14 H8 Cu N2 O6'
_chemical_formula_weight         363.76
_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 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   18.4309(18)
_cell_length_b                   18.4309(18)
_cell_length_c                   70.011(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     20596(6)
_cell_formula_units_Z            36
_cell_measurement_reflns_used    1073
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      55.9978
_cell_measurement_theta_min      2.7661
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.860
_exptl_absorpt_coefficient_mu    1.556
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.056
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             6588
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0798
_diffrn_reflns_av_unetI/netI     0.0875
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       75
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            8429
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        55.942
_diffrn_reflns_theta_max         55.942
_diffrn_reflns_theta_min         3.043
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1995
_reflns_number_total             2909
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.297
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.147
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.213
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2909
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.1133
_refine_ls_restrained_S_all      1.212
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3015
_refine_ls_wR_factor_ref         0.3499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2. Restrained distances
 C6A-O1A \\sim C6B-O1B
 with sigma of 0.02
 C6A-N2 \\sim C6B-N2
 with sigma of 0.02
 C4-C6A \\sim C4-C6B
 with sigma of 0.02
3. Restrained planarity
 N2, C6A, O1A, C4
 with sigma of 0.02
 O1B, C6B, C4, N2
 with sigma of 0.02
4. Others
 Fixed Sof: O1(0.5) O1A(0.7) O1B(0.3) O2W(0.5) H2A(0.7) H2B(0.3) C6A(0.7)
 C6B(0.3)
5.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), N2(H2B), C1(H1), C2(H2), C3(H3), C5(H5), C8(H8), C10(H10), C12(H12)
5.b Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,N1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.61801(7) 0.78274(8) 0.06784(2) 0.0536(7) Uani 1 1 d . . . . .
O1 O 0.7233(18) 1.0661(18) 0.1523(4) 0.160(8) Uiso 0.5 1 d . . P A 1
O1A O 0.4481(18) 1.0543(17) 0.1575(4) 0.235(10) Uiso 0.7 1 d D . P B 1
O1B O 0.675(2) 1.091(3) 0.1460(6) 0.161(14) Uiso 0.3 1 d D . P C 2
O2 O 0.3201(4) 0.8726(5) 0.08126(8) 0.0712(19) Uani 1 1 d . . . . .
O2W O 0.5484(18) 0.9496(18) 0.0523(4) 0.167(9) Uiso 0.5 1 d . . P . .
O3 O 0.2867(5) 0.9209(4) 0.10699(8) 0.0728(19) Uani 1 1 d . . . . .
O4 O 0.5621(4) 0.8329(5) 0.08260(10) 0.083(2) Uani 1 1 d . . . . .
O5 O 0.6393(4) 0.8667(5) 0.10907(9) 0.079(2) Uani 1 1 d . . . . .
N2 N 0.5489(8) 1.0326(8) 0.14831(18) 0.123(5) Uani 1 1 d D . . . .
H2A H 0.5980 1.0413 0.1512 0.147 Uiso 0.7 1 calc R . P D 1
H2B H 0.5075 1.0224 0.1557 0.147 Uiso 0.3 1 calc R . P E 2
C1 C 0.6702(4) 1.1977(4) 0.20868(9) 0.094(4) Uani 1 1 d . . . . .
H1 H 0.6958 1.2233 0.2201 0.113 Uiso 1 1 calc R . . . .
C2 C 0.7059(5) 1.2361(5) 0.19140(12) 0.138(6) Uani 1 1 d G . . . .
H2 H 0.7554 1.2874 0.1913 0.166 Uiso 1 1 calc R . . . .
C3 C 0.6675(7) 1.1979(7) 0.17430(9) 0.211(12) Uani 1 1 d G . . . .
H3 H 0.6914 1.2236 0.1627 0.253 Uiso 1 1 calc R . . . .
C4 C 0.5934(7) 1.1212(6) 0.17448(6) 0.136(7) Uani 1 1 d DG . . . .
C5 C 0.5577(5) 1.0828(4) 0.19176(8) 0.104(5) Uani 1 1 d G . . . .
H5 H 0.5081 1.0315 0.1919 0.125 Uiso 1 1 calc R . . . .
N1 N 0.5961(4) 1.1211(4) 0.20886(6) 0.062(2) Uani 1 1 d G . . . .
C6A C 0.5272(14) 1.0625(10) 0.1579(3) 0.113(6) Uiso 0.7 1 d D . P B 1
C6B C 0.604(2) 1.0779(15) 0.1552(3) 0.131(19) Uiso 0.3 1 d D . P C 2
C7 C 0.5159(7) 0.9825(8) 0.13206(15) 0.082(3) Uani 1 1 d . . . . .
C8 C 0.4431(7) 0.9683(7) 0.12364(14) 0.074(3) Uani 1 1 d . . . . .
H8 H 0.4126 0.9906 0.1291 0.089 Uiso 1 1 calc R . . . .
C9 C 0.4137(7) 0.9211(7) 0.10700(13) 0.067(3) Uani 1 1 d . . . . .
C10 C 0.4614(6) 0.8885(7) 0.09870(13) 0.067(3) Uani 1 1 d . . . . .
H10 H 0.4441 0.8592 0.0872 0.081 Uiso 1 1 calc R . . . .
C11 C 0.5343(6) 0.8998(7) 0.10752(14) 0.072(3) Uani 1 1 d . . . . .
C12 C 0.5612(7) 0.9477(8) 0.12439(16) 0.086(3) Uani 1 1 d . . . . .
H12 H 0.6097 0.9561 0.1305 0.103 Uiso 1 1 calc R . . . .
C13 C 0.5803(6) 0.8634(7) 0.09889(15) 0.068(3) Uani 1 1 d . . . . .
C14 C 0.3350(6) 0.9046(6) 0.09749(12) 0.057(2) Uani 1 1 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
Cu1 Cu1 2.668(2) 18_654 ?
Cu1 O2 1.909(6) 3_565 ?
Cu1 O3 2.012(7) 17_664 ?
Cu1 O4 1.984(7) . ?
Cu1 O5 1.952(7) 18_654 ?
Cu1 N1 2.14(5) 28_665 ?
O1A C6A 1.39(3) . ?
O1B C6B 1.37(3) . ?
O2 Cu1 1.909(6) 2_665 ?
O2 C14 1.246(10) . ?
O3 Cu1 2.012(7) 17_564 ?
O3 C14 1.262(10) . ?
O4 C13 1.242(12) . ?
O5 Cu1 1.952(7) 18_654 ?
O5 C13 1.276(11) . ?
N2 C6A 1.07(2) . ?
N2 C6B 1.06(3) . ?
N2 C7 1.399(15) . ?
C1 C2 1.3900 . ?
C1 N1 1.3900 . ?
C2 C3 1.3900 . ?
C3 C4 1.3900 . ?
C4 C5 1.3900 . ?
C4 C6A 1.64(2) . ?
C4 C6B 1.63(3) . ?
C5 N1 1.3900 . ?
N1 Cu1 2.142(5) 34_665 ?
C7 C8 1.366(14) . ?
C7 C12 1.389(15) . ?
C8 C9 1.392(14) . ?
C9 C10 1.415(13) . ?
C9 C14 1.482(13) . ?
C10 C11 1.395(13) . ?
C11 C12 1.408(14) . ?
C11 C13 1.451(15) . ?

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 85.35(19) 3_565 18_654 ?
O2 Cu1 O3 90.7(3) 3_565 17_664 ?
O2 Cu1 O4 89.4(3) 3_565 . ?
O2 Cu1 O5 171.6(3) 3_565 18_654 ?
O2 Cu1 N1 93.6(19) 3_565 28_665 ?
O3 Cu1 Cu1 81.75(18) 17_664 18_654 ?
O3 Cu1 N1 93.0(15) 17_664 28_665 ?
O4 Cu1 Cu1 80.7(2) . 18_654 ?
O4 Cu1 O3 162.4(3) . 17_664 ?
O4 Cu1 N1 104.6(16) . 28_665 ?
O5 Cu1 Cu1 86.4(2) 18_654 18_654 ?
O5 Cu1 O3 89.3(3) 18_654 17_664 ?
O5 Cu1 O4 88.2(4) 18_654 . ?
O5 Cu1 N1 94.7(18) 18_654 28_665 ?
N1 Cu1 Cu1 174.6(18) 28_665 18_654 ?
C14 O2 Cu1 124.3(6) . 2_665 ?
C14 O3 Cu1 122.8(6) . 17_564 ?
C13 O4 Cu1 127.1(7) . . ?
C13 O5 Cu1 121.1(7) . 18_654 ?
C6A N2 C7 134.7(15) . . ?
C6B N2 C7 145(2) . . ?
C2 C1 N1 120.0 . . ?
C1 C2 C3 120.0 . . ?
C4 C3 C2 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 C6A 133.9(7) . . ?
C3 C4 C6B 101.1(12) . . ?
C5 C4 C6A 105.8(7) . . ?
C5 C4 C6B 127.9(9) . . ?
N1 C5 C4 120.0 . . ?
C1 N1 Cu1 121.4(3) . 34_665 ?
C5 N1 Cu1 117.7(3) . 34_665 ?
C5 N1 C1 120.0 . . ?
O1A C6A C4 119(2) . . ?
N2 C6A O1A 125(2) . . ?
N2 C6A C4 116.2(19) . . ?
O1B C6B C4 130(3) . . ?
N2 C6B O1B 112(3) . . ?
N2 C6B C4 117(2) . . ?
C8 C7 N2 122.6(10) . . ?
C8 C7 C12 120.3(9) . . ?
C12 C7 N2 117.1(10) . . ?
C7 C8 C9 121.3(10) . . ?
C8 C9 C10 118.6(10) . . ?
C8 C9 C14 122.6(9) . . ?
C10 C9 C14 118.7(8) . . ?
C11 C10 C9 120.7(9) . . ?
C10 C11 C12 118.5(9) . . ?
C10 C11 C13 119.2(8) . . ?
C12 C11 C13 122.3(9) . . ?
C7 C12 C11 120.6(10) . . ?
O4 C13 O5 124.4(10) . . ?
O4 C13 C11 120.2(9) . . ?
O5 C13 C11 115.4(9) . . ?
O2 C14 O3 125.3(8) . . ?
O2 C14 C9 117.9(8) . . ?
O3 C14 C9 116.7(8) . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 0 6 3.788
0 0 12 7.593
0 0 18 11.432
0 0 24 15.323

_platon_squeeze_details          
;
TITL 1 in R-3c
CELL   18.4309   18.4309   70.0110     90.00     90.00    120.00
SPGR R-3c
# Solvent Accessible Volume =      8437
# Electrons Found in S.A.V. =      2129
# Note: Atoms in Void as Cxxx and Qxxx all others
Q101 0.047 0.546 0.266 !       1.61 eA-3
C102 1.001 1.000 0.250 !       1.26 eA-3
Q103 0.800 0.156 0.132 !       1.20 eA-3
C104 0.031 0.453 0.443 !       1.06 eA-3
C105 0.497 0.907 0.434 !       1.04 eA-3
C106 0.549 0.578 0.440 !       1.03 eA-3
C107 0.968 0.810 0.235 !       1.02 eA-3
C108 0.110 0.483 0.426 !       0.98 eA-3
C109 0.562 0.440 0.050 !       0.95 eA-3
Q110 0.849 0.405 0.141 !       0.92 eA-3
C111 0.169 0.215 0.274 !       0.92 eA-3
C112 0.878 0.535 0.078 !       0.92 eA-3
C113 0.903 0.794 0.226 !       0.91 eA-3
C114 0.686 0.124 0.102 !       0.91 eA-3
C115 0.136 0.173 0.305 !       0.91 eA-3
C116 0.732 0.559 0.137 !       0.90 eA-3
C117 0.032 0.858 0.306 !       0.90 eA-3
C118 0.625 0.268 0.095 !       0.90 eA-3
C119 1.000 0.999 0.274 !       0.89 eA-3
C120 0.203 0.487 0.379 !       0.88 eA-3
C121 0.536 0.372 0.548 !       0.87 eA-3
C122 0.409 0.270 0.601 !       0.87 eA-3
Q123 0.260 0.375 0.398 !       0.85 eA-3
C124 0.251 0.156 0.187 !       0.85 eA-3
C125 0.838 0.844 0.249 !       0.84 eA-3
C126 0.074 0.031 0.230 !       0.84 eA-3
Q127 0.710 0.921 0.770 !       0.84 eA-3
C128 0.840 0.953 0.272 !       0.83 eA-3
C129 0.853 0.941 0.267 !       0.83 eA-3
C130 0.200 0.565 0.371 !       0.82 eA-3
C131 0.298 0.596 0.411 !       0.82 eA-3
C132 0.562 0.280 0.050 !       0.82 eA-3
C133 0.147 0.952 0.269 !       0.81 eA-3
C134 0.281 0.517 0.888 !       0.81 eA-3
C135 0.521 0.796 0.399 !       0.81 eA-3
C136 0.250 0.530 0.402 !       0.80 eA-3
C137 0.147 0.528 0.938 !       0.80 eA-3
C138 0.864 0.922 0.764 !       0.80 eA-3
C139 0.468 0.866 0.430 !       0.80 eA-3
C140 0.567 0.391 0.082 !       0.80 eA-3
C141 0.309 0.732 0.383 !       0.80 eA-3
Q142 0.527 0.563 0.490 !       0.80 eA-3
C143 0.197 0.608 0.954 !       0.80 eA-3
C144 0.735 0.159 0.090 !       0.80 eA-3
C145 0.252 0.795 0.406 !       0.78 eA-3
C146 0.119 0.168 0.777 !       0.77 eA-3
C147 0.170 0.516 0.413 !       0.76 eA-3
Q148 0.454 0.453 0.250 !       0.76 eA-3
Q149 0.012 0.455 0.043 !       0.74 eA-3
Q150 0.262 0.502 0.472 !       0.74 eA-3
C151 0.128 0.611 0.409 !       0.74 eA-3
C152 0.561 0.343 0.096 !       0.73 eA-3
Q153 0.615 0.985 0.414 !       0.72 eA-3
C154 0.152 0.950 0.280 !       0.72 eA-3
Q155 0.797 0.118 0.918 !       0.71 eA-3
Q156 0.089 0.485 0.485 !       0.71 eA-3
C157 0.766 0.488 0.043 !       0.71 eA-3
Q158 0.390 0.511 0.449 !       0.71 eA-3
C159 0.465 0.108 0.099 !       0.70 eA-3
C160 0.166 0.232 0.285 !       0.70 eA-3
Q161 0.244 0.411 0.383 !       0.70 eA-3
C162 0.634 0.778 0.407 !       0.70 eA-3
C163 0.985 0.779 0.264 !       0.70 eA-3
C164 0.253 0.486 0.153 !       0.69 eA-3
C165 0.564 0.941 0.414 !       0.69 eA-3
C166 0.408 0.690 0.367 !       0.68 eA-3
C167 0.394 0.657 0.464 !       0.67 eA-3
C168 0.998 0.077 0.214 !       0.67 eA-3
C169 0.218 0.643 0.926 !       0.67 eA-3
C170 0.272 0.231 0.753 !       0.67 eA-3
Q171 0.427 0.434 0.470 !       0.66 eA-3
Q172 0.262 0.893 0.358 !       0.66 eA-3
C173 0.395 0.129 0.584 !       0.66 eA-3
Q174 0.596 0.769 0.051 !       0.65 eA-3
C175 0.875 0.936 0.469 !       0.65 eA-3
Q176 0.357 0.206 0.916 !       0.65 eA-3
Q177 1.000 0.783 0.304 !       0.64 eA-3
C178 0.158 0.595 0.398 !       0.64 eA-3
Q179 0.409 0.359 0.074 !       0.63 eA-3
C180 0.048 0.269 0.016 !       0.63 eA-3
C181 0.952 0.731 0.984 !       0.63 eA-3
Q182 0.858 0.125 0.418 !       0.63 eA-3
C183 0.616 0.386 0.106 !       0.63 eA-3
C184 0.402 0.634 0.469 !       0.62 eA-3
C185 0.374 0.642 0.132 !       0.62 eA-3
C186 0.245 0.250 0.249 !       0.62 eA-3
C187 0.067 0.034 0.020 !       0.61 eA-3
C188 0.620 0.062 0.317 !       0.61 eA-3
Q189 0.578 0.671 0.372 !       0.61 eA-3
C190 0.030 0.768 0.280 !       0.61 eA-3
Q191 0.331 0.152 0.153 !       0.61 eA-3
Q192 0.455 0.841 0.458 !       0.61 eA-3
C193 0.889 0.109 0.249 !       0.61 eA-3
Q194 0.610 0.825 0.055 !       0.60 eA-3
C195 0.263 0.987 0.256 !       0.60 eA-3
Q196 0.853 0.170 0.110 !       0.60 eA-3
Q197 0.926 0.308 0.591 !       0.60 eA-3
C198 0.173 0.013 0.263 !       0.60 eA-3
C199 0.401 0.289 0.848 !       0.60 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 543 72 ' '
2 -0.333 0.333 0.083 861 283 ' '
3 0.000 0.000 0.250 865 284 ' '
4 0.000 0.000 0.500 543 72 ' '
5 0.333 0.667 0.417 862 283 ' '
6 -0.333 0.333 0.583 862 283 ' '
7 0.000 0.000 0.750 865 284 ' '
8 0.333 0.667 0.917 862 283 ' '
9 0.333 0.667 0.167 545 72 ' '
10 0.333 0.667 0.667 546 72 ' '
11 0.667 0.333 0.333 544 72 ' '
12 0.667 0.333 0.833 544 72 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'

_vrf_THETM01_1_sq                
;
PROBLEM: _The value of sine(theta_max)/wavelength is less than 0.550
 Calculated sin(theta_max)/wavelength = 0.5365
RESPONSE: We have used Cu radiation, long exposure time, and best 
crystal to obtain best data set.
;
####################################################################### 
# 
# 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_1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1865057'
loop_
_audit_author_name
_audit_author_address
'Ji-Jun JIANG'
;Lehn Institute of Functional Materials, Sun Yat-Sen University
China
;
_audit_update_record             
;
2018-08-31 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;
_audit_creation_date             2018-08-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H8 Cu N2 O5'
_chemical_formula_sum            'C14 H8 Cu N2 O5'
_chemical_formula_weight         347.76
_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 0.0181 0.0091 '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 -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z+1/2'
'x-y, -y, -z+1/2'
'-x, -x+y, -z+1/2'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+5/6'
'x-y+2/3, -y+1/3, -z+5/6'
'-x+2/3, -x+y+1/3, -z+5/6'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+7/6'
'x-y+1/3, -y+2/3, -z+7/6'
'-x+1/3, -x+y+2/3, -z+7/6'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z-1/2'
'-x+y, y, z-1/2'
'x, x-y, z-1/2'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z-1/6'
'-x+y+2/3, y+1/3, z-1/6'
'x+2/3, x-y+1/3, z-1/6'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+1/6'
'-x+y+1/3, y+2/3, z+1/6'
'x+1/3, x-y+2/3, z+1/6'

_cell_length_a                   17.9678(16)
_cell_length_b                   17.9678(16)
_cell_length_c                   69.263(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     19365(4)
_cell_formula_units_Z            36
_cell_measurement_reflns_used    1388
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      55.7468
_cell_measurement_theta_min      3.1876
_shelx_estimated_absorpt_T_max   0.969
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    1.599
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.074
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             6300
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0741
_diffrn_reflns_av_unetI/netI     0.0981
_diffrn_reflns_Laue_measured_fraction_full 0.946
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       71
_diffrn_reflns_limit_l_min       -70
_diffrn_reflns_number            8016
_diffrn_reflns_point_group_measured_fraction_full 0.946
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        55.813
_diffrn_reflns_theta_max         55.813
_diffrn_reflns_theta_min         3.819
_diffrn_ambient_temperature      298.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.946
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1468
_reflns_number_total             2649
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    ?
_refine_diff_density_max         0.686
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.118
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.1619
_refine_ls_R_factor_gt           0.1193
_refine_ls_restrained_S_all      1.147
_refine_ls_shift/su_max          0.092
_refine_ls_shift/su_mean         0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3263
_refine_ls_wR_factor_ref         0.3650
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
2. Restrained distances
 N1-C1A = C1A-C2A = C2A-C3A = C3A-C4A = C4A-C5 = C5-N1
 1.38 with sigma of 0.02
 N1-C1B = C1B-C2B = C2B-C3B = C3B-C4B = C4B-C5 = C5-N1
 1.38 with sigma of 0.02
3. Restrained planarity
 N2, C4A, C6A, O5A
 with sigma of 0.1
 N2, C4B, C6B, O5B
 with sigma of 0.1
 N1, C1A, C2A, C3A, C4A, C5, C6A
 with sigma of 0.02
 N1, C1B, C2B, C3B, C4B, C5, C6B
 with sigma of 0.02
4. Others
 Fixed Sof: C1A(0.5) H1A(0.5) C2A(0.5) H2A(0.5) C3A(0.5) H3A(0.5) C2B(0.5)
 H2B(0.5) C3B(0.5) H3B(0.5) C4A(0.5) C4B(0.5) H5A(0.5) H5B(0.5) C6A(0.5)
 C6B(0.5) H2AA(0.5) H2BB(0.5) O5A(0.5) O5B(0.5) C1B(0.5) H1B(0.5)
5.a Aromatic/amide H refined with riding coordinates:
 C1A(H1A), C2A(H2A), C3A(H3A), C2B(H2B), C3B(H3B), C5(H5A), C5(H5B), C8(H8),
 C10(H10), C12(H12), N2(H2AA), N2(H2BB), C1B(H1B)
;
_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 0.15016(11) 0.76244(10) 0.06798(2) 0.0752(8) Uani 1 1 d . . . . .
C1A C 0.4960(9) 1.2041(10) 0.2104(3) 0.075(6) Uiso 0.5 1 d D . P A 1
H1A H 0.5070 1.2322 0.2222 0.090 Uiso 0.5 1 calc R . P A 1
C2A C 0.4694(13) 1.2361(17) 0.1956(3) 0.111(8) Uiso 0.5 1 d D . P A 1
H2A H 0.4627 1.2837 0.1974 0.133 Uiso 0.5 1 calc R . P A 1
C3A C 0.4531(15) 1.1957(15) 0.1780(4) 0.132(10) Uiso 0.5 1 d D . P A 1
H3A H 0.4355 1.2145 0.1674 0.158 Uiso 0.5 1 calc R . P A 1
C2B C 0.5553(18) 1.263(2) 0.1943(4) 0.171(14) Uiso 0.5 1 d D . P A 2
H2B H 0.5747 1.3212 0.1952 0.205 Uiso 0.5 1 calc R . P A 2
C3B C 0.5502(16) 1.2307(16) 0.1758(4) 0.142(11) Uiso 0.5 1 d D . P A 2
H3B H 0.5643 1.2648 0.1648 0.171 Uiso 0.5 1 calc R . P A 2
C4A C 0.4644(11) 1.1262(13) 0.1772(3) 0.088(6) Uiso 0.5 1 d D . P A 1
C4B C 0.5228(10) 1.1452(12) 0.1752(2) 0.065(5) Uiso 0.5 1 d D . P A 2
C5 C 0.4963(7) 1.0959(8) 0.19191(13) 0.092(3) Uiso 1 1 d D . . . .
H5A H 0.5088 1.0521 0.1898 0.111 Uiso 0.5 1 calc R . P A 1
H5B H 0.4708 1.0364 0.1911 0.111 Uiso 0.5 1 calc R . P A 2
C6A C 0.4461(18) 1.070(2) 0.1573(5) 0.135(11) Uiso 0.5 1 d . . P A 1
C6B C 0.5124(18) 1.094(2) 0.1555(4) 0.111(9) Uiso 0.5 1 d . . P A 2
C7 C 0.4501(9) 0.9836(10) 0.13506(15) 0.095(4) Uani 1 1 d . . . . .
C8 C 0.5156(9) 0.9753(10) 0.12601(15) 0.101(4) Uani 1 1 d . . . . .
H8 H 0.5700 1.0001 0.1315 0.121 Uiso 1 1 calc R . . . .
C9 C 0.4988(8) 0.9293(9) 0.10855(14) 0.090(4) Uani 1 1 d . . . . .
C10 C 0.4152(8) 0.8896(9) 0.10131(14) 0.090(4) Uani 1 1 d . . . . .
H10 H 0.4029 0.8575 0.0900 0.108 Uiso 1 1 calc R . . . .
C11 C 0.3518(9) 0.8957(9) 0.10994(14) 0.091(4) Uani 1 1 d . . . . .
C12 C 0.3685(10) 0.9414(9) 0.12748(15) 0.098(4) Uani 1 1 d . . . . .
H12 H 0.3239 0.9428 0.1340 0.118 Uiso 1 1 calc R . . . .
C13 C 0.5636(8) 0.9148(8) 0.09894(14) 0.076(3) Uani 1 1 d . . . . .
C14 C 0.2607(8) 0.8480(9) 0.10077(17) 0.089(4) Uani 1 1 d . . . . .
N1 N 0.5078(5) 1.1346(5) 0.20934(9) 0.076(3) Uani 1 1 d D . . . .
N2 N 0.4661(8) 1.0300(9) 0.15199(14) 0.109(4) Uani 1 1 d . . . . .
H2AA H 0.5000 1.0236 0.1597 0.131 Uiso 0.5 1 calc R . P A 1
H2BB H 0.4322 1.0016 0.1613 0.131 Uiso 0.5 1 calc R . P A 2
O1 O 0.6345(5) 0.9372(6) 0.10783(9) 0.089(3) Uani 1 1 d . . . . .
O2 O 0.5486(5) 0.8904(6) 0.08183(9) 0.087(2) Uani 1 1 d . . . . .
O3 O 0.2068(5) 0.8596(6) 0.11049(10) 0.099(3) Uani 1 1 d . . . . .
O4 O 0.2535(5) 0.8184(6) 0.08524(10) 0.096(3) Uani 1 1 d . . . . .
O5A O 0.383(2) 1.091(2) 0.1473(4) 0.194(10) Uiso 0.5 1 d . . P A 1
O5B O 0.592(2) 1.157(2) 0.1430(4) 0.221(13) Uiso 0.5 1 d . . P A 2
C1B C 0.5352(12) 1.2187(12) 0.2113(4) 0.107(9) Uiso 0.5 1 d D . P A 2
H1B H 0.5402 1.2447 0.2233 0.129 Uiso 0.5 1 calc R . P A 2


_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 2.718(2) 16_454 ?
Cu1 N1 2.170(8) 30_465 ?
Cu1 O1 2.023(8) 17_564 ?
Cu1 O2 1.896(8) 2_665 ?
Cu1 O3 1.925(8) 16_454 ?
Cu1 O4 2.005(8) . ?
C1A H1A 0.9300 . ?
C1A C2A 1.370(18) . ?
C1A N1 1.369(16) . ?
C2A H2A 0.9300 . ?
C2A C3A 1.370(18) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.363(18) . ?
C2B H2B 0.9300 . ?
C2B C3B 1.389(18) . ?
C2B C1B 1.365(19) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.360(19) . ?
C4A C5 1.404(16) . ?
C4A C6A 1.64(4) . ?
C4B C5 1.388(15) . ?
C4B C6B 1.61(4) . ?
C5 H5A 0.9300 . ?
C5 H5B 0.9300 . ?
C5 N1 1.358(10) . ?
C6A N2 1.02(4) . ?
C6A O5A 1.52(5) . ?
C6B N2 1.06(3) . ?
C6B O5B 1.56(4) . ?
C7 C8 1.407(19) . ?
C7 C12 1.375(18) . ?
C7 N2 1.383(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.410(15) . ?
C9 C10 1.396(16) . ?
C9 C13 1.472(17) . ?
C10 H10 0.9300 . ?
C10 C11 1.339(15) . ?
C11 C12 1.411(15) . ?
C11 C14 1.553(18) . ?
C12 H12 0.9300 . ?
C13 O1 1.285(13) . ?
C13 O2 1.245(11) . ?
C14 O3 1.279(15) . ?
C14 O4 1.178(13) . ?
N1 Cu1 2.171(8) 36_565 ?
N1 C1B 1.342(18) . ?
N2 H2AA 0.8600 . ?
N2 H2BB 0.8600 . ?
O1 Cu1 2.023(8) 17_664 ?
O2 Cu1 1.896(8) 3_565 ?
O3 Cu1 1.925(8) 16_454 ?
C1B H1B 0.9300 . ?

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
N1 Cu1 Cu1 171.9(2) 30_465 16_454 ?
O1 Cu1 Cu1 80.24(19) 17_564 16_454 ?
O1 Cu1 N1 92.4(3) 17_564 30_465 ?
O2 Cu1 Cu1 86.0(2) 2_665 16_454 ?
O2 Cu1 N1 91.0(3) 2_665 30_465 ?
O2 Cu1 O1 92.4(4) 2_665 17_564 ?
O2 Cu1 O3 174.7(3) 2_665 16_454 ?
O2 Cu1 O4 89.8(4) 2_665 . ?
O3 Cu1 Cu1 89.4(2) 16_454 16_454 ?
O3 Cu1 N1 93.9(3) 16_454 30_465 ?
O3 Cu1 O1 89.2(4) 16_454 17_564 ?
O3 Cu1 O4 86.8(4) 16_454 . ?
O4 Cu1 Cu1 76.2(2) . 16_454 ?
O4 Cu1 N1 111.3(3) . 30_465 ?
O4 Cu1 O1 156.2(3) . 17_564 ?
C2A C1A H1A 116.9 . . ?
C2A C1A N1 126(2) . . ?
N1 C1A H1A 117.0 . . ?
C1A C2A H2A 121.1 . . ?
C1A C2A C3A 118(3) . . ?
C3A C2A H2A 121.0 . . ?
C2A C3A H3A 122.2 . . ?
C4A C3A C2A 116(3) . . ?
C4A C3A H3A 122.2 . . ?
C3B C2B H2B 115.9 . . ?
C1B C2B H2B 115.9 . . ?
C1B C2B C3B 128(4) . . ?
C2B C3B H3B 123.1 . . ?
C4B C3B C2B 114(3) . . ?
C4B C3B H3B 123.1 . . ?
C3A C4A C5 127(2) . . ?
C3A C4A C6A 121(2) . . ?
C5 C4A C6A 111(2) . . ?
C3B C4B C5 120.9(19) . . ?
C3B C4B C6B 123.1(19) . . ?
C5 C4B C6B 115.9(17) . . ?
C4A C5 H5A 122.2 . . ?
C4B C5 H5B 120.1 . . ?
N1 C5 C4A 115.5(13) . . ?
N1 C5 C4B 119.8(12) . . ?
N1 C5 H5A 122.2 . . ?
N1 C5 H5B 120.1 . . ?
N2 C6A C4A 135(3) . . ?
N2 C6A O5A 125(4) . . ?
O5A C6A C4A 100(3) . . ?
C4B C6B O5B 105(3) . . ?
N2 C6B C4B 128(2) . . ?
N2 C6B O5B 127(3) . . ?
C8 C7 N2 120.6(13) . . ?
C12 C7 C8 119.3(11) . . ?
C12 C7 N2 120.0(12) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0(12) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C13 122.3(11) . . ?
C10 C9 C8 117.9(11) . . ?
C10 C9 C13 119.5(10) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 C9 122.7(11) . . ?
C11 C10 H10 118.6 . . ?
C10 C11 C12 119.3(13) . . ?
C10 C11 C14 118.5(11) . . ?
C12 C11 C14 122.1(11) . . ?
C7 C12 C11 120.5(12) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.7 . . ?
O1 C13 C9 118.4(9) . . ?
O2 C13 C9 116.2(10) . . ?
O2 C13 O1 124.9(10) . . ?
O3 C14 C11 111.7(11) . . ?
O4 C14 C11 118.1(10) . . ?
O4 C14 O3 129.2(11) . . ?
C1A N1 Cu1 119.5(8) . 36_565 ?
C5 N1 Cu1 116.7(7) . 36_565 ?
C5 N1 C1A 117.4(11) . . ?
C1B N1 Cu1 120.2(12) . 36_565 ?
C1B N1 C5 123.1(14) . . ?
C6A N2 C7 134(3) . . ?
C6A N2 H2AA 113.3 . . ?
C6B N2 C7 132(2) . . ?
C6B N2 H2BB 114.2 . . ?
C7 N2 H2AA 113.2 . . ?
C7 N2 H2BB 114.2 . . ?
C13 O1 Cu1 123.0(7) . 17_664 ?
C13 O2 Cu1 123.4(7) . 3_565 ?
C14 O3 Cu1 115.4(8) . 16_454 ?
C14 O4 Cu1 129.5(8) . . ?
C2B C1B H1B 123.1 . . ?
N1 C1B C2B 114(3) . . ?
N1 C1B H1B 123.1 . . ?

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
Cu1 N1 C1B C2B 174.4(8) 36_565 . . . ?
C1A C2A C3A C4A 0.7(13) . . . . ?
C2A C1A N1 Cu1 -147.7(7) . . . 36_565 ?
C2A C1A N1 C5 3.4(5) . . . . ?
C2A C3A C4A C5 -4.8(19) . . . . ?
C2A C3A C4A C6A 179.2(9) . . . . ?
C3A C4A C5 N1 8.0(17) . . . . ?
C3A C4A C6A N2 158(2) . . . . ?
C3A C4A C6A O5A -24.2(18) . . . . ?
C2B C3B C4B C5 5.0(15) . . . . ?
C2B C3B C4B C6B -179.5(9) . . . . ?
C3B C2B C1B N1 0.2(6) . . . . ?
C3B C4B C5 N1 -8.3(15) . . . . ?
C3B C4B C6B N2 -145(2) . . . . ?
C3B C4B C6B O5B 39.8(19) . . . . ?
C4A C5 N1 Cu1 145.3(9) . . . 36_565 ?
C4A C5 N1 C1A -6.6(11) . . . . ?
C4A C6A N2 C7 -179.6(16) . . . . ?
C4B C5 N1 Cu1 -170.4(9) . . . 36_565 ?
C4B C5 N1 C1B 7.7(11) . . . . ?
C4B C6B N2 C7 175.4(14) . . . . ?
C5 C4A C6A N2 -19(2) . . . . ?
C5 C4A C6A O5A 159.3(16) . . . . ?
C5 C4B C6B N2 30(2) . . . . ?
C5 C4B C6B O5B -144.5(16) . . . . ?
C5 N1 C1B C2B -3.6(5) . . . . ?
C6A C4A C5 N1 -175.7(8) . . . . ?
C6B C4B C5 N1 175.8(8) . . . . ?
C7 C8 C9 C10 -3(2) . . . . ?
C7 C8 C9 C13 -176.9(12) . . . . ?
C8 C7 C12 C11 -5(2) . . . . ?
C8 C7 N2 C6A 142(2) . . . . ?
C8 C7 N2 C6B 55(3) . . . . ?
C8 C9 C10 C11 2(2) . . . . ?
C8 C9 C13 O1 7.4(19) . . . . ?
C8 C9 C13 O2 -164.8(12) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C9 C10 C11 C14 -179.2(12) . . . . ?
C9 C13 O1 Cu1 169.6(9) . . . 17_664 ?
C9 C13 O2 Cu1 -169.2(8) . . . 3_565 ?
C10 C9 C13 O1 -166.3(12) . . . . ?
C10 C9 C13 O2 21.5(17) . . . . ?
C10 C11 C12 C7 4(2) . . . . ?
C10 C11 C14 O3 -179.9(12) . . . . ?
C10 C11 C14 O4 -10.5(17) . . . . ?
C11 C14 O3 Cu1 171.8(7) . . . 16_454 ?
C11 C14 O4 Cu1 -173.9(8) . . . . ?
C12 C7 C8 C9 5(2) . . . . ?
C12 C7 N2 C6A -41(3) . . . . ?
C12 C7 N2 C6B -128(2) . . . . ?
C12 C11 C14 O3 3.4(16) . . . . ?
C12 C11 C14 O4 172.8(13) . . . . ?
C13 C9 C10 C11 176.0(13) . . . . ?
C14 C11 C12 C7 -179.3(13) . . . . ?
N1 C1A C2A C3A -0.2(6) . . . . ?
N2 C7 C8 C9 -178.7(13) . . . . ?
N2 C7 C12 C11 178.3(14) . . . . ?
O1 C13 O2 Cu1 19.1(16) . . . 3_565 ?
O2 C13 O1 Cu1 -19.0(16) . . . 17_664 ?
O3 C14 O4 Cu1 -7(2) . . . . ?
O4 C14 O3 Cu1 3.9(18) . . . 16_454 ?
O5A C6A N2 C7 3(3) . . . . ?
O5B C6B N2 C7 -11(3) . . . . ?
C1B C2B C3B C4B -1.0(13) . . . . ?

loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
-1 2 0 4.922
0 3 0 8.547
-1 5 0 13.122
-3 6 0 14.917
0 6 0 17.292
-2 7 0 18.022
-4 8 0 20.074
-1 8 0 21.964
-2 3 1 7.559
-1 4 1 10.310
-5 6 1 16.025
-4 7 1 17.551
-1 7 1 18.969
-6 8 1 20.942
-3 8 1 20.302
0 1 2 3.113
-2 2 2 5.829
-3 4 2 10.370
0 4 2 11.503
-5 5 2 14.401
-1 6 2 16.065
-6 7 2 19.003
-3 7 2 17.588
0 7 2 20.335
-5 8 2 20.335
-2 8 2 20.974
-4 5 3 13.266
-1 5 3 13.266
-5 7 3 18.130
-2 7 3 18.130
-4 8 3 20.173
-4 4 4 11.719
0 5 4 14.577
-5 6 4 16.225
-2 6 4 15.420
-7 7 4 20.465
-4 7 4 17.735
-1 7 4 19.141
-6 8 4 21.101
-3 8 4 20.465
-1 6 5 16.343
-3 7 5 17.845
-5 8 5 20.562
-2 8 5 21.196
-3 3 6 9.377
-6 6 6 17.737
0 6 6 17.737
-2 7 6 18.452
-4 8 6 20.467
-4 7 7 18.135
-1 7 7 19.516
-6 8 7 21.447
-3 8 7 20.820
-1 6 8 16.849
-3 7 8 18.314
0 7 8 20.980
-5 8 8 20.980
-2 8 8 21.603
-2 7 9 18.977
-4 8 9 20.950
0 5 10 15.757
-1 7 10 20.084
-3 8 10 21.359
-5 8 11 21.578
0 6 12 19.019
-2 7 12 19.693
-4 8 12 21.611
-1 7 13 20.832
-3 8 13 22.071
-4 8 15 22.438
-1 7 16 21.745
0 6 18 21.005

_platon_squeeze_details          
;
TITL 1 in R-3c
CELL   17.9678   17.9678   69.2630     90.00     90.00    120.00
SPGR R-3c
# Solvent Accessible Volume =      7280
# Electrons Found in S.A.V. =      1323
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.469 0.144 0.081 !       0.96 eA-3
C102 0.155 0.156 0.250 !       0.82 eA-3
C103 0.346 0.783 0.430 !       0.81 eA-3
Q104 0.906 0.715 0.403 !       0.81 eA-3
Q105 0.800 0.238 0.429 !       0.80 eA-3
C106 0.264 0.794 0.402 !       0.79 eA-3
C107 0.888 0.813 0.473 !       0.78 eA-3
C108 0.252 0.269 0.242 !       0.78 eA-3
C109 0.546 0.907 0.165 !       0.77 eA-3
C110 0.905 0.999 0.024 !       0.75 eA-3
C111 0.645 0.562 0.078 !       0.75 eA-3
C112 0.767 0.270 0.109 !       0.74 eA-3
C113 0.876 0.998 0.492 !       0.74 eA-3
C114 0.752 1.000 0.226 !       0.73 eA-3
C115 0.099 0.936 0.776 !       0.73 eA-3
Q116 0.860 0.748 0.464 !       0.73 eA-3
C117 0.816 0.421 0.067 !       0.73 eA-3
C118 0.612 0.311 0.300 !       0.73 eA-3
C119 0.060 0.784 0.275 !       0.72 eA-3
C120 0.373 0.841 0.403 !       0.72 eA-3
C121 0.798 0.247 0.119 !       0.72 eA-3
C122 0.953 0.036 0.464 !       0.72 eA-3
C123 0.716 0.517 0.332 !       0.71 eA-3
C124 0.810 0.037 0.225 !       0.71 eA-3
C125 0.783 0.794 0.516 !       0.71 eA-3
C126 0.217 0.206 0.484 !       0.71 eA-3
Q127 0.365 0.217 0.398 !       0.70 eA-3
C128 0.429 0.854 0.944 !       0.70 eA-3
C129 0.206 0.564 0.211 !       0.70 eA-3
C130 0.876 0.529 0.821 !       0.70 eA-3
C131 0.528 0.141 0.836 !       0.69 eA-3
C132 0.174 0.248 0.016 !       0.69 eA-3
C133 0.778 0.844 0.012 !       0.68 eA-3
C134 0.222 0.156 0.988 !       0.68 eA-3
C135 0.048 0.175 1.001 !       0.68 eA-3
C136 0.688 0.455 0.340 !       0.68 eA-3
C137 0.833 0.346 0.339 !       0.67 eA-3
Q138 0.081 0.442 0.195 !       0.67 eA-3
Q139 0.546 0.663 0.267 !       0.67 eA-3
Q140 0.842 0.107 0.217 !       0.67 eA-3
C141 0.503 0.734 0.157 !       0.66 eA-3
C142 0.580 0.499 0.101 !       0.65 eA-3
Q143 0.623 0.719 0.383 !       0.65 eA-3
Q144 0.780 0.731 0.490 !       0.65 eA-3
C145 1.003 0.954 0.433 !       0.64 eA-3
C146 0.126 0.534 0.184 !       0.64 eA-3
C147 0.592 0.089 0.329 !       0.63 eA-3
Q148 0.886 0.585 0.847 !       0.63 eA-3
C149 0.484 0.153 0.832 !       0.63 eA-3
Q150 0.927 0.392 0.285 !       0.62 eA-3
Q151 0.480 0.219 0.376 !       0.62 eA-3
C152 0.433 0.251 0.840 !       0.62 eA-3
C153 0.411 0.620 0.457 !       0.61 eA-3
C154 0.925 0.074 0.470 !       0.61 eA-3
C155 0.669 0.284 0.767 !       0.61 eA-3
C156 0.593 0.344 0.078 !       0.60 eA-3
Q157 0.843 0.581 0.326 !       0.60 eA-3
C158 0.684 0.532 0.841 !       0.60 eA-3
Q159 0.247 0.203 0.020 !       0.60 eA-3
Q160 0.765 0.014 0.992 !       0.60 eA-3
Q161 0.765 0.830 0.491 !       0.60 eA-3
Q162 0.170 0.076 0.207 !       0.60 eA-3
Q163 0.594 0.843 0.008 !       0.59 eA-3
Q164 0.425 0.639 0.386 !       0.59 eA-3
C165 0.425 0.688 0.145 !       0.59 eA-3
Q166 0.347 0.045 0.495 !       0.59 eA-3
C167 0.431 0.782 0.439 !       0.58 eA-3
Q168 0.939 0.831 0.285 !       0.58 eA-3
C169 0.957 0.985 0.242 !       0.58 eA-3
Q170 0.359 0.781 0.388 !       0.58 eA-3
Q171 0.254 0.083 0.840 !       0.58 eA-3
Q172 0.979 0.096 0.783 !       0.58 eA-3
C173 0.025 0.074 0.047 !       0.58 eA-3
C174 0.661 0.377 0.890 !       0.58 eA-3
C175 0.956 0.967 0.016 !       0.58 eA-3
Q176 0.606 0.532 0.255 !       0.58 eA-3
C177 0.389 0.628 0.181 !       0.57 eA-3
C178 0.230 0.721 0.385 !       0.57 eA-3
C179 0.030 0.354 0.419 !       0.57 eA-3
Q180 0.760 0.156 0.356 !       0.57 eA-3
Q181 0.581 0.732 0.454 !       0.57 eA-3
Q182 0.726 0.118 0.413 !       0.57 eA-3
C183 0.689 0.282 0.882 !       0.56 eA-3
C184 0.311 0.718 0.118 !       0.56 eA-3
Q185 0.927 0.402 0.178 !       0.56 eA-3
Q186 0.343 0.390 0.501 !       0.56 eA-3
C187 0.764 0.562 0.074 !       0.55 eA-3
Q188 0.302 0.955 0.393 !       0.55 eA-3
Q189 0.828 0.534 0.441 !       0.55 eA-3
C190 0.796 0.925 0.004 !       0.54 eA-3
Q191 0.395 0.479 0.191 !       0.54 eA-3
C192 0.658 0.472 0.055 !       0.54 eA-3
Q193 0.093 0.656 0.122 !       0.54 eA-3
Q194 0.671 0.781 0.378 !       0.54 eA-3
C195 0.110 0.529 0.409 !       0.54 eA-3
C196 0.986 0.953 0.273 !       0.53 eA-3
Q197 0.232 0.861 0.092 !       0.53 eA-3
C198 0.760 0.996 0.008 !       0.53 eA-3
Q199 0.596 0.326 0.890 !       0.53 eA-3
;
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.000 0.000 453 109 ' '
2 -0.333 0.333 0.083 761 113 ' '
3 0.000 0.000 0.250 760 113 ' '
4 0.000 0.000 0.500 453 109 ' '
5 0.333 0.667 0.417 764 114 ' '
6 -0.333 0.333 0.583 761 113 ' '
7 0.000 0.000 0.750 760 113 ' '
8 0.333 0.667 0.917 764 114 ' '
9 0.333 0.667 0.167 453 108 ' '
10 0.333 0.667 0.667 453 108 ' '
11 0.667 0.333 0.333 452 108 ' '
12 0.667 0.333 0.833 451 108 ' '

_platon_squeeze_void_probe_radius 1.20

_olex2_submission_special_instructions 'No special instructions were received'

_vrf_THETM01_1                   
;
PROBLEM: _The value of sine(theta_max)/wavelength is less than 0.550
 Calculated sin(theta_max)/wavelength = 0.5365  
RESPONSE: We have used Cu radiation, long exposure time, and best 
crystal to obtain best data set.
;

