# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# 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_dp
_database_code_depnum_ccdc_archive 'CCDC 1492066'
_audit_update_record             
;
2016-07-11 deposited with the CCDC.
2016-09-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H10 Cu N2 O8'
_chemical_formula_weight         481.86

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'

_space_group_crystal_system      hexagonal
_space_group_IT_number           171
_space_group_name_H-M_alt        'P 62'
_space_group_name_Hall           'P 62'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x-y, x, z+1/3'
'-y, x-y, z+2/3'
'-x, -y, z'
'-x+y, -x, z+1/3'
'y, -x+y, z+2/3'

_cell_length_a                   22.7393(15)
_cell_length_b                   22.7393(15)
_cell_length_c                   10.7316(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     4805.6(8)
_cell_formula_units_Z            6
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    51818
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.999
_exptl_crystal_F_000             1458
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.715
_shelx_estimated_absorpt_T_min   0.830
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  0.925
_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                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51818
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.610
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7386
_reflns_number_gt                5668
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component perfect inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2500P)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_abs_structure_details 
;
 Refined as a perfect inversion twin.
;
_refine_ls_abs_structure_Flack   0.5
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7386
_refine_ls_number_parameters     278
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.1148
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.3149
_refine_ls_wR_factor_gt          0.2992
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

# SQUEEZE RESULTS (APPEND TO CIF)
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
1 -0.004 -0.002 -0.026 2251.4 253.3
_platon_squeeze_details          
; ?
;

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 0.33149(4) 0.33142(4) 0.3540(2) 0.0382(4) Uani 1 1 d . . . . .
O1 O 0.2843(4) 0.3712(4) 0.4378(7) 0.0547(18) Uani 1 1 d . . . . .
O2 O 0.3816(4) 0.4644(6) 0.4061(11) 0.096(4) Uani 1 1 d . . . . .
O3 O 0.0882(3) 0.3732(4) 0.6003(9) 0.061(2) Uani 1 1 d . . . . .
O4 O 0.0884(6) 0.4679(7) 0.6451(14) 0.124(6) Uani 1 1 d . . . . .
O5 O 0.6427(4) 0.6915(4) 0.5083(7) 0.0580(19) Uani 1 1 d . . . . .
O6 O 0.7367(5) 0.7938(4) 0.5019(11) 0.083(3) Uani 1 1 d . . . . .
O7 O 0.7365(5) 0.9461(4) 0.8650(11) 0.079(3) Uani 1 1 d . . . . .
O8 O 0.6427(4) 0.9506(3) 0.8684(9) 0.063(2) Uani 1 1 d . . . . .
N1 N 0.4291(7) 0.7881(8) 0.6101(14) 0.088(4) Uani 1 1 d . . . . .
N2 N 0.3243(6) 0.6950(8) 0.5759(10) 0.078(3) Uani 1 1 d . . . . .
C1 C 0.3197(5) 0.4321(7) 0.4431(10) 0.061(3) Uani 1 1 d . . . . .
C2 C 0.2900(6) 0.4738(6) 0.4847(10) 0.056(3) Uani 1 1 d . U . . .
C3 C 0.2221(5) 0.4406(4) 0.5217(11) 0.0480(19) Uani 1 1 d . . . . .
H3A H 0.1974 0.3935 0.5170 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1896(6) 0.4744(6) 0.5650(14) 0.074(4) Uani 1 1 d . . . . .
C5 C 0.2314(10) 0.5471(7) 0.573(2) 0.140(11) Uani 1 1 d D . . . .
H5A H 0.2118 0.5737 0.5887 0.168 Uiso 1 1 calc R U . . .
C6 C 0.3091(7) 0.5806(8) 0.5567(16) 0.085(4) Uani 1 1 d D U . . .
C7 C 0.3265(8) 0.5430(9) 0.4943(17) 0.108(6) Uani 1 1 d . U . . .
H7A H 0.3677 0.5651 0.4520 0.129 Uiso 1 1 calc R U . . .
C8 C 0.1138(5) 0.4333(6) 0.6020(11) 0.057(3) Uani 1 1 d . . . . .
C9 C 0.3467(7) 0.6493(9) 0.5709(13) 0.074(4) Uani 1 1 d . . . . .
C10 C 0.4222(9) 0.6840(9) 0.5959(14) 0.095(6) Uani 1 1 d . . . . .
H10A H 0.4430 0.6579 0.6023 0.114 Uiso 1 1 calc R U . . .
C11 C 0.4626(10) 0.7568(13) 0.6100(14) 0.104(6) Uani 1 1 d . . . . .
C12 C 0.3649(7) 0.7610(8) 0.5904(12) 0.070(3) Uani 1 1 d . . . . .
C13 C 0.3335(10) 0.8023(10) 0.5898(14) 0.092(5) Uani 1 1 d . . . . .
H13A H 0.2857 0.7743 0.5738 0.138 Uiso 1 1 calc R U . . .
H13B H 0.3400 0.8240 0.6694 0.138 Uiso 1 1 calc R U . . .
H13C H 0.3536 0.8362 0.5259 0.138 Uiso 1 1 calc R U . . .
C14 C 0.5365(5) 0.7832(5) 0.6377(10) 0.077(4) Uani 1 1 d G . . . .
C15 C 0.5719(4) 0.7545(6) 0.5854(10) 0.107(6) Uani 1 1 d G . . . .
H15A H 0.5500 0.7178 0.5313 0.129 Uiso 1 1 calc R U . . .
C16 C 0.6398(4) 0.7804(5) 0.6136(9) 0.068(3) Uani 1 1 d G . . . .
C17 C 0.6723(3) 0.8349(4) 0.6940(8) 0.048(2) Uani 1 1 d G . . . .
H17A H 0.7180 0.8523 0.7130 0.058 Uiso 1 1 calc R U . . .
C18 C 0.6369(4) 0.8636(4) 0.7463(10) 0.079(4) Uani 1 1 d G . . . .
C19 C 0.5690(5) 0.8377(5) 0.7182(10) 0.101(5) Uani 1 1 d G . . . .
H19A H 0.5452 0.8570 0.7533 0.121 Uiso 1 1 calc R U . . .
C20 C 0.6769(6) 0.7530(7) 0.5377(11) 0.064(3) Uani 1 1 d . . . . .
C21 C 0.6754(6) 0.9242(6) 0.8353(11) 0.060(3) 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 O8 1.902(8) 5_564 ?
Cu1 O5 1.915(7) 4_665 ?
Cu1 O1 1.938(7) . ?
Cu1 O3 1.972(7) 6_554 ?
Cu1 C1 2.615(11) . ?
Cu1 C8 2.627(10) 6_554 ?
Cu1 C20 2.691(12) 4_665 ?
Cu1 C21 2.687(10) 5_564 ?
O1 C1 1.205(14) . ?
O2 C1 1.282(13) . ?
O3 C8 1.188(13) . ?
O3 Cu1 1.972(7) 2 ?
O4 C8 1.273(15) . ?
O5 C20 1.254(15) . ?
O5 Cu1 1.915(7) 4_665 ?
O6 C20 1.265(15) . ?
O7 C21 1.262(15) . ?
O8 C21 1.217(13) . ?
O8 Cu1 1.902(8) 3_665 ?
N1 C11 1.28(2) . ?
N1 C12 1.29(2) . ?
N2 C12 1.32(2) . ?
N2 C9 1.370(19) . ?
C1 C2 1.482(14) . ?
C2 C7 1.37(2) . ?
C2 C3 1.395(16) . ?
C3 C4 1.386(14) . ?
C3 H3A 0.9300 . ?
C4 C5 1.439(19) . ?
C4 C8 1.546(15) . ?
C5 C6 1.545(19) . ?
C5 H5A 0.9300 . ?
C6 C7 1.29(2) . ?
C6 C9 1.36(2) . ?
C7 H7A 0.9300 . ?
C8 Cu1 2.627(10) 2 ?
C9 C10 1.51(2) . ?
C10 C11 1.45(3) . ?
C10 H10A 0.9300 . ?
C11 C14 1.50(2) . ?
C12 C13 1.44(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.383(5) . ?
C14 C15 1.383(5) . ?
C15 C16 1.383(5) . ?
C15 H15A 0.9300 . ?
C16 C17 1.383(5) . ?
C16 C20 1.512(13) . ?
C17 C18 1.383(5) . ?
C17 H17A 0.9300 . ?
C18 C19 1.383(5) . ?
C18 C21 1.540(12) . ?
C19 H19A 0.9300 . ?
C20 Cu1 2.691(12) 4_665 ?
C21 Cu1 2.687(10) 3_665 ?

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
O8 Cu1 O5 178.1(4) 5_564 4_665 ?
O8 Cu1 O1 86.9(3) 5_564 . ?
O5 Cu1 O1 92.4(3) 4_665 . ?
O8 Cu1 O3 92.6(4) 5_564 6_554 ?
O5 Cu1 O3 88.2(3) 4_665 6_554 ?
O1 Cu1 O3 175.9(4) . 6_554 ?
O8 Cu1 C1 82.8(4) 5_564 . ?
O5 Cu1 C1 95.8(4) 4_665 . ?
O1 Cu1 C1 25.6(3) . . ?
O3 Cu1 C1 158.3(4) 6_554 . ?
O8 Cu1 C8 97.6(4) 5_564 6_554 ?
O5 Cu1 C8 82.4(4) 4_665 6_554 ?
O1 Cu1 C8 158.9(4) . 6_554 ?
O3 Cu1 C8 25.2(3) 6_554 6_554 ?
C1 Cu1 C8 134.3(3) . 6_554 ?
O8 Cu1 C20 156.8(4) 5_564 4_665 ?
O5 Cu1 C20 25.0(4) 4_665 4_665 ?
O1 Cu1 C20 97.7(4) . 4_665 ?
O3 Cu1 C20 81.2(4) 6_554 4_665 ?
C1 Cu1 C20 110.7(4) . 4_665 ?
C8 Cu1 C20 86.2(3) 6_554 4_665 ?
O8 Cu1 C21 23.7(4) 5_564 5_564 ?
O5 Cu1 C21 157.8(4) 4_665 5_564 ?
O1 Cu1 C21 80.5(4) . 5_564 ?
O3 Cu1 C21 97.4(4) 6_554 5_564 ?
C1 Cu1 C21 86.9(3) . 5_564 ?
C8 Cu1 C21 111.3(4) 6_554 5_564 ?
C20 Cu1 C21 134.7(4) 4_665 5_564 ?
C1 O1 Cu1 110.4(6) . . ?
C8 O3 Cu1 110.0(7) . 2 ?
C20 O5 Cu1 114.7(8) . 4_665 ?
C21 O8 Cu1 117.3(8) . 3_665 ?
C11 N1 C12 125.8(17) . . ?
C12 N2 C9 123.5(12) . . ?
O1 C1 O2 123.8(10) . . ?
O1 C1 C2 119.4(9) . . ?
O2 C1 C2 116.6(12) . . ?
O1 C1 Cu1 44.0(5) . . ?
O2 C1 Cu1 79.9(6) . . ?
C2 C1 Cu1 161.6(7) . . ?
C7 C2 C3 118.1(10) . . ?
C7 C2 C1 123.4(11) . . ?
C3 C2 C1 118.4(10) . . ?
C4 C3 C2 123.3(9) . . ?
C4 C3 H3A 118.3 . . ?
C2 C3 H3A 118.3 . . ?
C3 C4 C5 115.3(10) . . ?
C3 C4 C8 119.5(11) . . ?
C5 C4 C8 125.2(10) . . ?
C4 C5 C6 119.7(11) . . ?
C4 C5 H5A 120.1 . . ?
C6 C5 H5A 120.1 . . ?
C7 C6 C9 126.2(13) . . ?
C7 C6 C5 112.7(13) . . ?
C9 C6 C5 117.3(11) . . ?
C6 C7 C2 126.1(12) . . ?
C6 C7 H7A 117.0 . . ?
C2 C7 H7A 117.0 . . ?
O3 C8 O4 127.1(10) . . ?
O3 C8 C4 116.6(9) . . ?
O4 C8 C4 115.7(11) . . ?
O3 C8 Cu1 44.9(5) . 2 ?
O4 C8 Cu1 82.3(7) . 2 ?
C4 C8 Cu1 158.6(7) . 2 ?
C6 C9 N2 128.0(13) . . ?
C6 C9 C10 121.1(14) . . ?
N2 C9 C10 110.7(16) . . ?
C11 C10 C9 121.6(19) . . ?
C11 C10 H10A 119.2 . . ?
C9 C10 H10A 119.2 . . ?
N1 C11 C10 115.0(17) . . ?
N1 C11 C14 130(2) . . ?
C10 C11 C14 114.9(18) . . ?
N1 C12 N2 123.1(14) . . ?
N1 C12 C13 120.3(15) . . ?
N2 C12 C13 116.6(15) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.0 . . ?
C19 C14 C11 118.0(9) . . ?
C15 C14 C11 122.0(9) . . ?
C14 C15 C16 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 C20 123.2(6) . . ?
C15 C16 C20 116.2(6) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17A 120.0 . . ?
C16 C17 H17A 120.0 . . ?
C19 C18 C17 120.0 . . ?
C19 C18 C21 122.0(6) . . ?
C17 C18 C21 118.0(6) . . ?
C14 C19 C18 120.0 . . ?
C14 C19 H19A 120.0 . . ?
C18 C19 H19A 120.0 . . ?
O5 C20 O6 125.6(11) . . ?
O5 C20 C16 115.6(10) . . ?
O6 C20 C16 118.5(11) . . ?
O5 C20 Cu1 40.3(5) . 4_665 ?
O6 C20 Cu1 88.1(7) . 4_665 ?
C16 C20 Cu1 146.4(7) . 4_665 ?
O8 C21 O7 123.8(10) . . ?
O8 C21 C18 114.1(10) . . ?
O7 C21 C18 122.0(9) . . ?
O8 C21 Cu1 39.0(6) . 3_665 ?
O7 C21 Cu1 88.1(7) . 3_665 ?
C18 C21 Cu1 147.6(7) . 3_665 ?

_refine_diff_density_max         1.447
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.144



