# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_d_sq
_database_code_depnum_ccdc_archive 'CCDC 1406720'
_audit_update_record             
;
2015-07-13 deposited with the CCDC.
2015-09-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ZJU-9
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 Cu N0 O5'
_chemical_formula_weight         305.72

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

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'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+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'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+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-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+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-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+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   18.4284(17)
_cell_length_b                   18.4284(17)
_cell_length_c                   40.081(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     11788(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.775
_exptl_crystal_F_000             2754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.839
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_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      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40869
_diffrn_reflns_av_unetI/netI     0.0847
_diffrn_reflns_av_R_equivalents  0.2433
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         1.524
_diffrn_reflns_theta_max         26.077
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2861
_reflns_number_gt                1489
_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.
 
 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.
;

_computing_data_collection       'Bruker XSCANS'
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1439P)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         2861
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1494
_refine_ls_R_factor_gt           0.0800
_refine_ls_wR_factor_ref         0.2598
_refine_ls_wR_factor_gt          0.2093
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
Cu1 Cu 0.04881(5) 0.52441(3) 0.02667(2) 0.0609(4) Uani 1 2 d S T P . .
O1B O 0.1319(5) 0.5659(2) 0.06878(18) 0.127(3) Uani 1 2 d S T P . .
C1 C -0.1772(3) 0.6457(6) 0.1514(2) 0.071(2) Uani 1 2 d S T P . .
O1 O -0.0276(3) 0.5612(3) 0.04305(10) 0.0801(12) Uani 1 1 d . . . . .
O3 O -0.1085(2) 0.5200(3) -0.00193(9) 0.0811(12) Uani 1 1 d . . . . .
C3C C -0.1567(4) 0.6865(7) 0.1216(2) 0.099(3) Uani 1 2 d S T P . .
C3B C -0.1254(4) 0.6196(4) 0.07318(15) 0.0790(17) Uani 1 1 d . . . . .
H3B H -0.0755 0.6320 0.0837 0.095 Uiso 1 1 calc R U . . .
C8 C -0.1142(5) 0.7715(9) 0.1208(4) 0.257(13) Uani 1 2 d S T P . .
H8 H -0.0998 0.8004 0.1007 0.308 Uiso 1 2 calc R U P . .
C7 C -0.0922(5) 0.8155(9) 0.1521(4) 0.36(2) Uani 1 2 d S T P . .
H7 H -0.0631 0.8738 0.1522 0.426 Uiso 1 2 calc R U P . .
C2 C -0.2205(3) 0.5591(5) 0.02741(18) 0.069(2) Uani 1 2 d S T P . .
H2 H -0.2340 0.5320 0.0069 0.083 Uiso 1 2 calc R U P . .
C5 C -0.1450(3) 0.5786(4) 0.04223(13) 0.0660(14) Uani 1 1 d . . . . .
C5C C -0.2203(5) 0.5593(10) 0.1521(3) 0.182(7) Uani 1 2 d S T P . .
H5C H -0.2353 0.5295 0.1322 0.219 Uiso 1 2 calc R U P . .
C5B C -0.1791(3) 0.6418(6) 0.0882(2) 0.085(3) Uani 1 2 d S T P . .
C3 C -0.0903(3) 0.5504(4) 0.02686(13) 0.0634(14) 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 O3 1.941(4) 6 ?
Cu1 O3 1.941(4) 19_565 ?
Cu1 O1 1.957(4) . ?
Cu1 O1 1.957(4) 24_565 ?
Cu1 O1B 2.146(6) . ?
Cu1 Cu1 2.6451(16) 19_565 ?
C1 C3C 1.361(14) . ?
C1 C5C 1.378(16) . ?
C1 C1 1.396(16) 25_465 ?
O1 C3 1.251(6) . ?
O3 C3 1.252(6) . ?
O3 Cu1 1.941(4) 19_565 ?
C3C C8 1.357(17) . ?
C3C C5B 1.515(12) . ?
C3B C5B 1.385(7) . ?
C3B C5 1.403(8) . ?
C8 C7 1.437(17) . ?
C7 C5C 1.34(2) 25_465 ?
C2 C5 1.384(6) 23_455 ?
C2 C5 1.384(6) . ?
C5 C3 1.481(8) . ?
C5C C7 1.34(2) 25_465 ?
C5B C3B 1.385(7) 23_455 ?

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 O3 89.8(3) 6 19_565 ?
O3 Cu1 O1 88.80(19) 6 . ?
O3 Cu1 O1 167.39(16) 19_565 . ?
O3 Cu1 O1 167.39(16) 6 24_565 ?
O3 Cu1 O1 88.80(19) 19_565 24_565 ?
O1 Cu1 O1 89.9(3) . 24_565 ?
O3 Cu1 O1B 95.66(19) 6 . ?
O3 Cu1 O1B 95.66(19) 19_565 . ?
O1 Cu1 O1B 97.0(2) . . ?
O1 Cu1 O1B 97.0(2) 24_565 . ?
O3 Cu1 Cu1 82.89(11) 6 19_565 ?
O3 Cu1 Cu1 82.89(11) 19_565 19_565 ?
O1 Cu1 Cu1 84.49(12) . 19_565 ?
O1 Cu1 Cu1 84.50(12) 24_565 19_565 ?
O1B Cu1 Cu1 177.9(2) . 19_565 ?
C3C C1 C5C 119.8(9) . . ?
C3C C1 C1 122.7(11) . 25_465 ?
C5C C1 C1 117.5(12) . 25_465 ?
C3 O1 Cu1 122.5(4) . . ?
C3 O3 Cu1 125.2(4) . 19_565 ?
C8 C3C C1 119.9(10) . . ?
C8 C3C C5B 116.8(11) . . ?
C1 C3C C5B 123.3(9) . . ?
C5B C3B C5 121.0(6) . . ?
C3C C8 C7 117.9(14) . . ?
C5C C7 C8 121.2(14) 25_465 . ?
C5 C2 C5 122.0(7) 23_455 . ?
C2 C5 C3B 118.4(6) . . ?
C2 C5 C3 120.2(5) . . ?
C3B C5 C3 121.3(5) . . ?
C7 C5C C1 120.8(11) 25_465 . ?
C3B C5B C3B 119.2(8) 23_455 . ?
C3B C5B C3C 120.4(4) 23_455 . ?
C3B C5B C3C 120.3(4) . . ?
O1 C3 O3 124.7(5) . . ?
O1 C3 C5 117.7(5) . . ?
O3 C3 C5 117.5(5) . . ?

_refine_diff_density_max         1.179
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.113

_shelxl_version_number           2014/6




