# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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. 
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data_FJI-Y6
_database_code_depnum_ccdc_archive 'CCDC 1586541'
_audit_update_record             
;
2017-11-21 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 Cu In0.50 N2 O3.67, N O3 [+ solvent]'
_chemical_formula_sum            'C15 H14 Cu In0.50 N3 O6.67'
_chemical_formula_weight         463.91

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'
In In 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   21.8599(3)
_cell_length_b                   21.8599(3)
_cell_length_c                   30.9566(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     12810.9(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    200.0(1)
_cell_measurement_reflns_used    18492
_cell_measurement_theta_min      3.6550
_cell_measurement_theta_max      72.8750

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.722
_exptl_crystal_F_000             2782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    2.986
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.54114
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200.0(1)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            50173
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.045
_diffrn_reflns_theta_max         73.485
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4674
_reflns_number_gt                3472
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1337P)²+42.0815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4674
_refine_ls_number_parameters     207
_refine_ls_number_restraints     212
_refine_ls_R_factor_all          0.1016
_refine_ls_R_factor_gt           0.0758
_refine_ls_wR_factor_ref         0.2486
_refine_ls_wR_factor_gt          0.2052
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.001
_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
In1 In 0.72042(2) 0.27958(2) 0.750000 0.0395(3) Uani 1 4 d S TU P . .
Cu1 Cu 0.45297(13) 0.03797(16) 0.48375(8) 0.1125(10) Uani 0.5 1 d . U P . .
O1 O 0.6547(2) 0.2064(2) 0.70024(11) 0.0605(10) Uani 1 1 d . U . . .
O2 O 0.666667 0.333333 0.750000 0.035(2) Uani 1 12 d S TU P . .
O3 O 0.7769(2) 0.2231(2) 0.750000 0.063(2) Uani 1 4 d S TU P . .
O4 O 0.5367(4) 0.0733(9) 0.5181(5) 0.089(4) Uani 0.5 2 d S TU P . .
O5 O 0.5027(4) 0.0054(9) 0.4488(5) 0.090(4) Uani 0.5 2 d S TU P . .
O7 O 0.8147(5) 0.1853(5) 0.6138(5) 0.206(7) Uani 1 2 d DS TU P . .
O8 O 0.8616(8) 0.2324(7) 0.6714(5) 0.264(7) Uani 1 1 d . U . . .
N1 N 0.4011(6) 0.0585(7) 0.5257(4) 0.075(3) Uani 0.5 1 d D U P . .
N2 N 0.3675(6) -0.0117(8) 0.4520(4) 0.080(3) Uani 0.5 1 d D U P . .
N3 N 0.8151(5) 0.1849(5) 0.6533(5) 0.157(6) Uani 1 2 d DS TU P . .
C1 C 0.3099(5) -0.0114(7) 0.4795(4) 0.083(3) Uani 0.5 1 d DG U P . .
H1 H 0.299659 -0.047935 0.500221 0.099 Uiso 0.5 1 d R U P . .
C2 C 0.2380(6) -0.0365(7) 0.4604(4) 0.109(5) Uani 0.5 1 d G U P . .
H2B H 0.223539 -0.079110 0.444846 0.131 Uiso 0.5 1 d R U P . .
H2C H 0.240448 -0.002113 0.440529 0.131 Uiso 0.5 1 d R U P . .
C3 C 0.1844(5) -0.0490(7) 0.4947(4) 0.119(5) Uani 0.5 1 d G U P . .
H3B H 0.177564 -0.087505 0.512367 0.143 Uiso 0.5 1 d R U P . .
H3C H 0.140459 -0.061348 0.481437 0.143 Uiso 0.5 1 d R U P . .
C4 C 0.2075(5) 0.0154(7) 0.5224(4) 0.084(3) Uani 0.5 1 d G U P . .
H4A H 0.174189 0.004566 0.545048 0.101 Uiso 0.5 1 d R U P . .
H4B H 0.208506 0.052128 0.505453 0.101 Uiso 0.5 1 d R U P . .
C5 C 0.2794(6) 0.0404(7) 0.5415(4) 0.095(4) Uani 0.5 1 d G U P . .
H5A H 0.276943 0.006053 0.561364 0.114 Uiso 0.5 1 d R U P . .
H5B H 0.293863 0.083070 0.557037 0.114 Uiso 0.5 1 d R U P . .
C6 C 0.3330(5) 0.0530(6) 0.5072(4) 0.108(4) Uani 0.5 1 d DG U P . .
H6 H 0.342478 0.092805 0.489996 0.129 Uiso 0.5 1 d R U P . .
C7 C 0.5948(2) 0.1897(4) 0.6853(2) 0.0530(18) Uani 1 2 d S TU P . .
C8 C 0.5788(6) 0.1577(12) 0.6427(8) 0.056(6) Uani 0.5 2 d S TU P . .
C9 C 0.5136(8) 0.1382(7) 0.6217(4) 0.049(3) Uani 0.5 1 d . U P . .
H9 H 0.479492 0.146201 0.636319 0.059 Uiso 0.5 1 d R U P . .
C10 C 0.4272(7) 0.0871(8) 0.5637(4) 0.061(3) Uani 0.5 1 d . U P . .
H10 H 0.397104 0.094975 0.582619 0.073 Uiso 0.5 1 d R U P . .
C11 C 0.4973(8) 0.1068(8) 0.5792(5) 0.067(3) Uani 0.5 1 d . U P . .
C12 C 0.5482(5) 0.0965(11) 0.5574(6) 0.066(4) Uani 0.5 2 d S TU P . .
C13 C 0.4327(5) -0.1346(11) 0.3504(7) 0.049(5) Uani 0.5 2 d S TU P . .
C14 C 0.3913(9) -0.1114(8) 0.3667(5) 0.059(4) Uani 0.5 1 d . U P . .
H14 H 0.347084 -0.124920 0.352815 0.071 Uiso 0.5 1 d R U P . .
C15 C 0.4779(6) -0.0443(11) 0.4192(7) 0.072(5) Uani 0.5 2 d S TU P . .
C16 C 0.4093(8) -0.0697(9) 0.4025(5) 0.067(3) Uani 0.5 1 d . U P . .
C17 C 0.3585(10) -0.0488(10) 0.4191(6) 0.084(5) Uani 0.5 1 d . U P . .
H17 H 0.314909 -0.065561 0.403680 0.101 Uiso 0.5 1 d R U P . .


_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
In1 O2 2.0351(7) . ?
In1 O3 2.139(8) . ?
In1 O1 2.167(3) 10_666 ?
In1 O1 2.167(3) 21_665 ?
In1 O1 2.167(3) 16_557 ?
In1 O1 2.167(3) . ?
Cu1 Cu1 1.755(7) 7_556 ?
Cu1 N2 1.899(11) . ?
Cu1 O5 1.905(8) . ?
Cu1 O4 1.913(8) . ?
Cu1 N1 1.920(10) . ?
Cu1 N1 2.295(13) 7_556 ?
Cu1 N2 2.441(14) 7_556 ?
Cu1 Cu1 2.886(4) 19_655 ?
O1 C7 1.259(5) . ?
O4 C12 1.30(2) . ?
O4 O5 1.81(2) 13_656 ?
O5 C15 1.31(2) . ?
O7 N3 1.225(9) . ?
O8 N3 1.169(14) . ?
N1 N2 1.123(17) 7_556 ?
N1 C10 1.318(15) . ?
N1 C1 1.526(13) 7_556 ?
N1 C6 1.543(11) . ?
N1 C17 1.73(2) 7_556 ?
N2 C17 1.253(17) . ?
N2 C1 1.523(11) . ?
N2 C10 1.524(17) 7_556 ?
C1 C1 1.34(2) 7_556 ?
C1 C5 1.499(11) 7_556 ?
C1 C2 1.503(5) . ?
C1 C6 1.504(5) . ?
C2 C4 1.403(14) 7_556 ?
C2 C3 1.503(5) . ?
C2 C6 1.52(2) 7_556 ?
C3 C4 1.503(5) . ?
C3 C5 1.579(17) 7_556 ?
C4 C5 1.503(5) . ?
C4 C4 1.50(3) 7_556 ?
C5 C6 1.503(5) . ?
C7 C8 1.45(3) . ?
C7 C13 1.517(19) 13_656 ?
C8 C9 1.43(2) 19_655 ?
C8 C9 1.43(2) . ?
C8 C14 1.48(2) 13_656 ?
C8 C14 1.48(2) 7_556 ?
C9 C11 1.443(17) . ?
C9 C13 1.49(2) 13_656 ?
C9 C16 1.497(18) 7_556 ?
C10 C11 1.450(19) . ?
C11 C12 1.413(16) . ?
C13 C14 1.338(19) 19_655 ?
C13 C14 1.339(19) . ?
C14 C16 1.360(19) . ?
C15 C16 1.411(16) 19_655 ?
C15 C16 1.411(16) . ?
C16 C17 1.49(2) . ?

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 In1 O3 180.0 . . ?
O2 In1 O1 93.75(12) . 10_666 ?
O3 In1 O1 86.25(12) . 10_666 ?
O2 In1 O1 93.75(12) . 21_665 ?
O3 In1 O1 86.25(12) . 21_665 ?
O1 In1 O1 90.6(2) 10_666 21_665 ?
O2 In1 O1 93.75(12) . 16_557 ?
O3 In1 O1 86.25(12) . 16_557 ?
O1 In1 O1 88.9(2) 10_666 16_557 ?
O1 In1 O1 172.5(2) 21_665 16_557 ?
O2 In1 O1 93.76(12) . . ?
O3 In1 O1 86.24(12) . . ?
O1 In1 O1 172.5(2) 10_666 . ?
O1 In1 O1 88.9(2) 21_665 . ?
O1 In1 O1 90.6(2) 16_557 . ?
Cu1 Cu1 N2 83.7(5) 7_556 . ?
Cu1 Cu1 O5 93.5(6) 7_556 . ?
N2 Cu1 O5 94.3(4) . . ?
Cu1 Cu1 O4 88.2(6) 7_556 . ?
N2 Cu1 O4 170.8(7) . . ?
O5 Cu1 O4 81.8(4) . . ?
Cu1 Cu1 N1 77.1(5) 7_556 . ?
N2 Cu1 N1 87.6(4) . . ?
O5 Cu1 N1 170.2(7) . . ?
O4 Cu1 N1 95.0(4) . . ?
O5 Cu1 N1 96.8(5) . 7_556 ?
O4 Cu1 N1 142.8(7) . 7_556 ?
N1 Cu1 N1 80.2(5) . 7_556 ?
N2 Cu1 N2 86.7(5) . 7_556 ?
O5 Cu1 N2 143.9(7) . 7_556 ?
O4 Cu1 N2 91.6(5) . 7_556 ?
N1 Cu1 N2 67.8(3) 7_556 7_556 ?
Cu1 Cu1 Cu1 90.0 7_556 19_655 ?
N2 Cu1 Cu1 134.2(3) . 19_655 ?
N1 Cu1 Cu1 135.0(3) . 19_655 ?
N1 Cu1 Cu1 126.3(3) 7_556 19_655 ?
N2 Cu1 Cu1 122.9(3) 7_556 19_655 ?
C7 O1 In1 133.3(4) . . ?
In1 O2 In1 120.000(1) . 3_655 ?
In1 O2 In1 120.0 . 14_667 ?
In1 O2 In1 120.0 3_655 14_667 ?
C12 O4 O5 75.2(13) . 13_656 ?
C12 O4 Cu1 129.9(4) . . ?
O5 O4 Cu1 91.5(7) 13_656 . ?
C12 O4 Cu1 129.9(4) . 19_655 ?
O5 O4 Cu1 91.5(7) 13_656 19_655 ?
Cu1 O4 Cu1 98.0(6) . 19_655 ?
C15 O5 O4 78.8(14) . 13_656 ?
C15 O5 Cu1 128.9(5) . . ?
O4 O5 Cu1 86.8(7) 13_656 . ?
C15 O5 Cu1 128.9(5) . 19_655 ?
O4 O5 Cu1 86.8(7) 13_656 19_655 ?
Cu1 O5 Cu1 98.5(5) . 19_655 ?
N2 N1 C10 76.8(12) 7_556 . ?
N2 N1 C1 68.2(8) 7_556 7_556 ?
C10 N1 C1 119.5(12) . 7_556 ?
N2 N1 C6 101.7(11) 7_556 . ?
C10 N1 C6 122.8(10) . . ?
C1 N1 C17 98.9(11) 7_556 7_556 ?
C6 N1 C17 119.2(11) . 7_556 ?
N2 N1 Cu1 103.6(9) 7_556 . ?
C10 N1 Cu1 123.2(9) . . ?
C1 N1 Cu1 112.3(7) 7_556 . ?
C6 N1 Cu1 112.9(7) . . ?
C17 N1 Cu1 123.1(9) 7_556 . ?
C10 N1 Cu1 109.0(10) . 7_556 ?
C1 N1 Cu1 89.9(7) 7_556 7_556 ?
C6 N1 Cu1 116.5(7) . 7_556 ?
C17 N1 Cu1 87.7(9) 7_556 7_556 ?
N1 N2 C17 93.5(15) 7_556 . ?
C17 N2 C1 126.4(13) . . ?
C1 N2 C10 107.7(11) . 7_556 ?
N1 N2 Cu1 95.4(10) 7_556 . ?
C17 N2 Cu1 125.6(11) . . ?
C1 N2 Cu1 106.7(7) . . ?
C10 N2 Cu1 121.7(9) 7_556 . ?
C17 N2 Cu1 117.2(12) . 7_556 ?
C1 N2 Cu1 89.7(7) . 7_556 ?
C10 N2 Cu1 89.3(9) 7_556 7_556 ?
O8 N3 O8 123(2) . 21_665 ?
O8 N3 O7 118.5(10) . . ?
O8 N3 O7 118.5(10) 21_665 . ?
C6 C1 C1 81(2) 7_556 7_556 ?
C6 C1 C5 72.6(9) 7_556 7_556 ?
C1 C1 C5 121.9(9) 7_556 7_556 ?
C6 C1 C2 73.6(10) 7_556 . ?
C1 C1 C2 118.3(5) 7_556 . ?
C6 C1 C6 114.3(16) 7_556 . ?
C5 C1 C6 115.8(7) 7_556 . ?
C2 C1 C6 111.5 . . ?
C6 C1 N2 115.6(14) 7_556 . ?
C1 C1 N2 122.0(6) 7_556 . ?
C5 C1 N2 116.0(13) 7_556 . ?
C2 C1 N2 119.6(9) . . ?
C6 C1 N2 115.6(8) . . ?
C6 C1 N1 73.7(12) 7_556 7_556 ?
C1 C1 N1 106.8(10) 7_556 7_556 ?
C5 C1 N1 113.8(12) 7_556 7_556 ?
C2 C1 N1 118.0(8) . 7_556 ?
C6 C1 N1 129.8(9) . 7_556 ?
C5 C2 C4 150(9) 7_556 7_556 ?
C5 C2 C1 86(6) 7_556 . ?
C4 C2 C1 121.3(10) 7_556 . ?
C5 C2 C3 130(10) 7_556 . ?
C1 C2 C3 111.5 . . ?
C5 C2 C6 79(9) 7_556 7_556 ?
C4 C2 C6 116.3(14) 7_556 7_556 ?
C3 C2 C6 89.9(8) . 7_556 ?
C4 C3 C4 73.6(18) 7_556 . ?
C4 C3 C2 111.5 . . ?
C4 C3 C5 69.1(14) 7_556 7_556 ?
C4 C3 C5 114.5(9) . 7_556 ?
C4 C3 C3 51.1(15) 7_556 7_556 ?
C2 C3 C3 88.1(6) . 7_556 ?
C5 C3 C3 91.3(10) 7_556 7_556 ?
C3 C4 C2 79.5(10) 7_556 7_556 ?
C3 C4 C5 78.9(10) 7_556 . ?
C3 C4 C3 102.7(18) 7_556 . ?
C2 C4 C3 109.4(8) 7_556 . ?
C5 C4 C3 111.5 . . ?
C3 C4 C4 73.5(17) 7_556 7_556 ?
C2 C4 C4 117.4(8) 7_556 7_556 ?
C5 C4 C4 119.02(18) . 7_556 ?
C2 C5 C1 90(6) 7_556 7_556 ?
C2 C5 C6 97(9) 7_556 . ?
C1 C5 C4 115.1(6) 7_556 . ?
C6 C5 C4 111.5 . . ?
C1 C5 C3 107.6(11) 7_556 7_556 ?
C6 C5 C3 87.7(7) . 7_556 ?
C1 C6 C5 72.1(13) 7_556 . ?
C5 C6 C1 111.5 . . ?
C1 C6 C2 71.4(15) 7_556 7_556 ?
C1 C6 C2 107.8(9) . 7_556 ?
C1 C6 N1 71.8(8) 7_556 . ?
C5 C6 N1 112.6(9) . . ?
C1 C6 N1 98.3(8) . . ?
C2 C6 N1 115.8(12) 7_556 . ?
O1 C7 O1 127.0(6) . 19_655 ?
O1 C7 C8 116.1(3) . . ?
O1 C7 C8 116.1(3) 19_655 . ?
O1 C7 C13 116.1(3) . 13_656 ?
O1 C7 C13 116.1(3) 19_655 13_656 ?
C13 C8 C9 88(3) 13_656 19_655 ?
C13 C8 C9 88(3) 13_656 . ?
C9 C8 C9 117(2) 19_655 . ?
C13 C8 C7 89(5) 13_656 . ?
C9 C8 C7 121.5(10) 19_655 . ?
C9 C8 C7 121.5(10) . . ?
C9 C8 C14 115.0(17) . 13_656 ?
C7 C8 C14 115.2(13) . 13_656 ?
C9 C8 C14 115.0(17) 19_655 7_556 ?
C7 C8 C14 115.2(13) . 7_556 ?
C14 C8 C14 102.9(18) 13_656 7_556 ?
C14 C9 C8 83(3) 7_556 . ?
C14 C9 C11 101(2) 7_556 . ?
C8 C9 C11 122.0(15) . . ?
C11 C9 C13 121.1(14) . 13_656 ?
C8 C9 C16 117.1(14) . 7_556 ?
C13 C9 C16 104.7(13) 13_656 7_556 ?
C17 C10 N1 101.0(17) 7_556 . ?
C17 C10 C11 91.6(18) 7_556 . ?
N1 C10 C11 125.4(11) . . ?
C11 C10 N2 118.7(11) . 7_556 ?
N1 C10 C16 128.0(11) . 7_556 ?
N2 C10 C16 97.3(10) 7_556 7_556 ?
C16 C11 C12 100.7(19) 7_556 . ?
C16 C11 C9 75.4(14) 7_556 . ?
C12 C11 C9 118.9(13) . . ?
C16 C11 C10 90.8(17) 7_556 . ?
C12 C11 C10 126.5(11) . . ?
C9 C11 C10 114.6(12) . . ?
C12 C11 C14 116.6(13) . 7_556 ?
C10 C11 C14 112.4(12) . 7_556 ?
C9 C11 C15 104.7(13) . 13_656 ?
C10 C11 C15 118.9(11) . 13_656 ?
C14 C11 C15 88.7(12) 7_556 13_656 ?
C12 C11 C17 126.6(12) . 7_556 ?
C9 C11 C17 104.0(12) . 7_556 ?
C14 C11 C17 92.0(12) 7_556 7_556 ?
C15 C11 C17 96.5(11) 13_656 7_556 ?
C15 C12 O4 106.4(18) 13_656 . ?
C15 C12 C11 80.3(13) 13_656 . ?
O4 C12 C11 119.7(8) . . ?
C15 C12 C11 80.3(13) 13_656 19_655 ?
O4 C12 C11 119.7(8) . 19_655 ?
C11 C12 C11 120.5(16) . 19_655 ?
O4 C12 C16 123.4(11) . 7_556 ?
C11 C12 C16 107.3(14) 19_655 7_556 ?
O4 C12 C16 123.4(11) . 13_656 ?
C11 C12 C16 107.3(14) . 13_656 ?
C16 C12 C16 84.6(13) 7_556 13_656 ?
C8 C13 C14 97(3) 13_656 19_655 ?
C8 C13 C14 97(3) 13_656 . ?
C14 C13 C14 119.9(19) 19_655 . ?
C14 C13 C9 120.0(15) . 13_656 ?
C8 C13 C9 73(3) 13_656 7_556 ?
C14 C13 C9 120.0(15) 19_655 7_556 ?
C9 C13 C9 108.9(18) 13_656 7_556 ?
C8 C13 C7 73(5) 13_656 13_656 ?
C14 C13 C7 120.0(9) 19_655 13_656 ?
C14 C13 C7 120.0(9) . 13_656 ?
C9 C13 C7 113.0(10) 13_656 13_656 ?
C9 C13 C7 113.0(10) 7_556 13_656 ?
C9 C14 C13 92(3) 7_556 . ?
C9 C14 C16 90(2) 7_556 . ?
C13 C14 C16 122.6(16) . . ?
C9 C14 C8 73(3) 7_556 13_656 ?
C16 C14 C8 122.7(17) . 13_656 ?
C13 C14 C11 115.4(16) . 7_556 ?
C8 C14 C11 105.0(16) 13_656 7_556 ?
C12 C15 O5 99.6(18) 13_656 . ?
C12 C15 C16 86.7(13) 13_656 19_655 ?
O5 C15 C16 120.1(8) . 19_655 ?
C12 C15 C16 86.7(13) 13_656 . ?
O5 C15 C16 120.1(8) . . ?
C16 C15 C16 119.8(16) 19_655 . ?
O5 C15 C11 118.5(11) . 7_556 ?
C16 C15 C11 113.3(14) 19_655 7_556 ?
O5 C15 C11 118.5(11) . 13_656 ?
C16 C15 C11 113.3(14) . 13_656 ?
C11 C15 C11 91.9(15) 7_556 13_656 ?
C11 C16 C14 93.4(16) 7_556 . ?
C11 C16 C15 92.2(19) 7_556 . ?
C14 C16 C15 117.2(14) . . ?
C11 C16 C17 89.0(17) 7_556 . ?
C14 C16 C17 118.5(14) . . ?
C15 C16 C17 124.1(12) . . ?
C15 C16 C9 118.3(14) . 7_556 ?
C17 C16 C9 114.1(13) . 7_556 ?
C14 C16 C10 114.8(12) . 7_556 ?
C15 C16 C10 120.4(12) . 7_556 ?
C9 C16 C10 98.1(11) 7_556 7_556 ?
C14 C16 C12 111.3(13) . 13_656 ?
C17 C16 C12 116.2(12) . 13_656 ?
C10 C16 C12 92.6(10) 7_556 13_656 ?
C10 C17 N2 88.5(18) 7_556 . ?
C10 C17 C16 88.5(18) 7_556 . ?
N2 C17 C16 125.4(15) . . ?
N2 C17 C11 117.3(15) . 7_556 ?
C16 C17 N1 116.0(14) . 7_556 ?
C11 C17 N1 90.6(11) 7_556 7_556 ?

_refine_diff_density_max         1.202
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.105



####################################################################### 
# 
# 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_ligand
_database_code_depnum_ccdc_archive 'CCDC 1586542'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H46 Cu2 N6 O14'
_chemical_formula_weight         865.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   8.73490(10)
_cell_length_b                   13.3687(2)
_cell_length_c                   15.7886(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.319(2)
_cell_angle_gamma                90
_cell_volume                     1786.42(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    4804
_cell_measurement_theta_min      5.2050
_cell_measurement_theta_max      73.1930

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    2.143
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57040
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6857
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.392
_diffrn_reflns_theta_max         73.325
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.684
_diffrn_reflns_point_group_measured_fraction_full 0.714
_reflns_number_total             4913
_reflns_number_gt                4812
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.343
_reflns_Friedel_fraction_max     0.366
_reflns_Friedel_fraction_full    0.402

_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²+1.5417P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1194 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(3)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4913
_refine_ls_number_parameters     489
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_ref         0.1095
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_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 0.41652(7) 0.40147(5) 0.78250(4) 0.02047(18) Uani 1 1 d . . . . .
Cu2 Cu 0.57263(7) 0.57116(5) 0.72458(4) 0.02097(19) Uani 1 1 d . . . . .
O1 O 1.2935(3) 0.4339(3) 1.0662(2) 0.0203(7) Uani 1 1 d . . . . .
H1O H 1.368573 0.415109 1.105237 0.024 Uiso 1 1 d R U . . .
O2 O 1.1695(4) 0.3128(3) 1.1212(2) 0.0263(8) Uani 1 1 d . . . . .
O3 O -0.1641(8) 0.6327(6) 0.3703(4) 0.091(2) Uani 1 1 d . U . . .
O4 O -0.2871(5) 0.5251(5) 0.4251(3) 0.0633(17) Uani 1 1 d . . . . .
H4O H -0.363754 0.549934 0.390810 0.076 Uiso 1 1 d R U . . .
O5 O 0.6221(3) 0.4610(3) 0.80426(19) 0.0158(7) Uani 1 1 d . . . . .
O6 O 0.3648(4) 0.5117(3) 0.7035(2) 0.0198(7) Uani 1 1 d . . . . .
O7 O 0.3668(4) 0.5432(3) 0.8858(2) 0.0246(8) Uani 1 1 d . . . . .
O8 O 0.4858(4) 0.6658(3) 0.8366(2) 0.0241(8) Uani 1 1 d . . . . .
O9 O 0.2544(4) 0.6887(3) 0.8611(3) 0.0349(10) Uani 1 1 d . . . . .
O10 O 0.5036(5) 0.3119(4) 0.6639(3) 0.0389(11) Uani 1 1 d . . . . .
O11 O 0.6308(5) 0.4343(4) 0.6187(3) 0.0381(11) Uani 1 1 d . . . . .
O12 O 0.7119(5) 0.2808(4) 0.6183(3) 0.0418(11) Uani 1 1 d . . . . .
O13 O 1.5322(4) 0.3679(3) 1.1880(2) 0.0233(7) Uani 1 1 d . . . . .
H13O H 1.543108 0.308592 1.201275 0.028 Uiso 1 1 d R U . . .
O14 O -0.5056(5) 0.6155(5) 0.2937(4) 0.0661(17) Uani 1 1 d . . . . .
H14 H -0.513359 0.674690 0.305577 0.079 Uiso 1 1 d R U . . .
N1 N 0.4790(4) 0.2988(3) 0.8731(2) 0.0169(8) Uani 1 1 d . . . . .
H1 H 0.530754 0.242358 0.849164 0.020 Uiso 1 1 calc R U . . .
N2 N 0.1983(5) 0.3542(4) 0.7588(3) 0.0279(10) Uani 1 1 d . . . . .
H2 H 0.141323 0.400076 0.790622 0.034 Uiso 1 1 calc R U . . .
N3 N 0.7848(4) 0.6309(3) 0.7577(2) 0.0178(8) Uani 1 1 d . . . . .
H3 H 0.790236 0.679099 0.806780 0.021 Uiso 1 1 calc R U . . .
N4 N 0.5153(5) 0.6610(4) 0.6236(3) 0.0256(10) Uani 1 1 d . . . . .
H4 H 0.529647 0.622880 0.571590 0.031 Uiso 1 1 calc R U . . .
N5 N 0.3655(5) 0.6321(3) 0.8606(2) 0.0183(8) Uani 1 1 d . . . . .
N6 N 0.6173(5) 0.3434(4) 0.6336(3) 0.0290(11) Uani 1 1 d . . . . .
C1 C 1.1668(5) 0.3802(4) 1.0681(3) 0.0176(9) Uani 1 1 d . . . . .
C2 C 0.8941(5) 0.4903(3) 0.8637(3) 0.0139(8) Uani 1 1 d . . . . .
C3 C 0.7517(5) 0.4439(4) 0.8672(3) 0.0126(8) Uani 1 1 d . . . . .
C4 C 0.7446(5) 0.3776(3) 0.9366(3) 0.0141(9) Uani 1 1 d . . . . .
C5 C 0.8822(5) 0.3572(4) 0.9992(3) 0.0161(9) Uani 1 1 d . . . . .
H5 H 0.880100 0.310079 1.043946 0.019 Uiso 1 1 calc R U . . .
C6 C 1.0249(4) 0.4047(4) 0.9982(3) 0.0138(8) Uani 1 1 d . . . . .
C7 C 1.0288(5) 0.4725(4) 0.9313(3) 0.0150(9) Uani 1 1 d . . . . .
H7 H 1.124174 0.506901 0.931788 0.018 Uiso 1 1 calc R U . . .
C8 C -0.1658(7) 0.5786(7) 0.4272(4) 0.0437(16) Uani 1 1 d . . . . .
C9 C 0.2384(5) 0.5256(4) 0.6375(3) 0.0164(9) Uani 1 1 d . . . . .
C10 C 0.2300(6) 0.6103(4) 0.5833(3) 0.0231(10) Uani 1 1 d . . . . .
C11 C 0.0984(6) 0.6212(4) 0.5131(3) 0.0254(11) Uani 1 1 d . . . . .
H11 H 0.094922 0.674937 0.473361 0.030 Uiso 1 1 calc R U . . .
C12 C -0.0251(6) 0.5564(5) 0.5003(3) 0.0251(12) Uani 1 1 d . . . . .
C13 C -0.0204(5) 0.4754(4) 0.5553(3) 0.0199(10) Uani 1 1 d . . . . .
H13 H -0.108983 0.431973 0.547043 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1132(5) 0.4569(4) 0.6229(3) 0.0171(9) Uani 1 1 d . . . . .
C15 C 0.5903(5) 0.3388(4) 0.9507(3) 0.0198(9) Uani 1 1 d . . . . .
H15A H 0.614215 0.285480 0.995617 0.024 Uiso 1 1 calc R U . . .
H15B H 0.537698 0.393879 0.974529 0.024 Uiso 1 1 calc R U . . .
C16 C 0.9086(4) 0.5530(4) 0.7858(3) 0.0171(9) Uani 1 1 d . . . . .
H16A H 1.013154 0.586217 0.800266 0.020 Uiso 1 1 calc R U . . .
H16B H 0.905481 0.507706 0.735785 0.020 Uiso 1 1 calc R U . . .
C17 C 0.3511(6) 0.6934(4) 0.6044(4) 0.0316(12) Uani 1 1 d . . . . .
H17A H 0.332039 0.740111 0.554168 0.038 Uiso 1 1 calc R U . . .
H17B H 0.334471 0.731056 0.655332 0.038 Uiso 1 1 calc R U . . .
C18 C 0.1177(6) 0.3592(4) 0.6685(3) 0.0286(11) Uani 1 1 d . . . . .
H18A H 0.007294 0.337507 0.662914 0.034 Uiso 1 1 calc R U . . .
H18B H 0.166964 0.309665 0.636839 0.034 Uiso 1 1 calc R U . . .
C19 C 0.3270(5) 0.2621(3) 0.8898(3) 0.0149(9) Uani 1 1 d . . . . .
H19 H 0.289365 0.312992 0.926447 0.018 Uiso 1 1 calc R U . . .
C20 C 0.3431(5) 0.1633(4) 0.9373(3) 0.0211(10) Uani 1 1 d . . . . .
H20A H 0.418138 0.170618 0.995285 0.025 Uiso 1 1 calc R U . . .
H20B H 0.386499 0.112775 0.903750 0.025 Uiso 1 1 calc R U . . .
C21 C 0.1836(6) 0.1269(4) 0.9494(3) 0.0246(10) Uani 1 1 d . . . . .
H21A H 0.197024 0.060223 0.977666 0.030 Uiso 1 1 calc R U . . .
H21B H 0.145607 0.173621 0.988397 0.030 Uiso 1 1 calc R U . . .
C22 C 0.0610(6) 0.1201(4) 0.8619(3) 0.0225(10) Uani 1 1 d . . . . .
H22A H -0.042151 0.100111 0.871987 0.027 Uiso 1 1 calc R U . . .
H22B H 0.093582 0.068086 0.825226 0.027 Uiso 1 1 calc R U . . .
C23 C 0.0435(5) 0.2204(4) 0.8138(3) 0.0230(10) Uani 1 1 d . . . . .
H23A H 0.001474 0.271043 0.847827 0.028 Uiso 1 1 calc R U . . .
H23B H -0.032330 0.213315 0.756072 0.028 Uiso 1 1 calc R U . . .
C24 C 0.2048(5) 0.2554(4) 0.8012(3) 0.0186(9) Uani 1 1 d . . . . .
H24 H 0.242661 0.205179 0.764113 0.022 Uiso 1 1 calc R U . . .
C25 C 0.7973(5) 0.6881(4) 0.6769(3) 0.0188(10) Uani 1 1 d . . . . .
H25 H 0.812013 0.638732 0.631968 0.023 Uiso 1 1 calc R U . . .
C26 C 0.9350(6) 0.7606(4) 0.6941(3) 0.0241(11) Uani 1 1 d . . . . .
H26A H 1.035529 0.722787 0.709743 0.029 Uiso 1 1 calc R U . . .
H26B H 0.930482 0.804311 0.743997 0.029 Uiso 1 1 calc R U . . .
C27 C 0.9307(6) 0.8250(4) 0.6134(3) 0.0260(11) Uani 1 1 d . . . . .
H27A H 1.017435 0.874652 0.627402 0.031 Uiso 1 1 calc R U . . .
H27B H 0.947821 0.781983 0.565521 0.031 Uiso 1 1 calc R U . . .
C28 C 0.7740(6) 0.8792(4) 0.5831(3) 0.0263(10) Uani 1 1 d . . . . .
H28A H 0.760949 0.926451 0.629061 0.032 Uiso 1 1 calc R U . . .
H28B H 0.773904 0.918411 0.529856 0.032 Uiso 1 1 calc R U . . .
C29 C 0.6374(6) 0.8069(4) 0.5635(3) 0.0259(11) Uani 1 1 d . . . . .
H29A H 0.644197 0.764341 0.513205 0.031 Uiso 1 1 calc R U . . .
H29B H 0.536914 0.844696 0.547060 0.031 Uiso 1 1 calc R U . . .
C30 C 0.6375(6) 0.7407(4) 0.6422(3) 0.0222(10) Uani 1 1 d . . . . .
H30 H 0.617132 0.784061 0.689800 0.027 Uiso 1 1 calc R U . . .
C31 C 1.6820(6) 0.4141(5) 1.2035(4) 0.0339(12) Uani 1 1 d . . . . .
H31A H 1.676099 0.481329 1.227222 0.051 Uiso 1 1 calc R U . . .
H31B H 1.714490 0.418787 1.148534 0.051 Uiso 1 1 calc R U . . .
H31C H 1.759292 0.374148 1.245595 0.051 Uiso 1 1 calc R U . . .
C32 C -0.6522(8) 0.5781(7) 0.2624(5) 0.0589(19) Uani 1 1 d . . . . .
H32A H -0.712252 0.584177 0.306989 0.071 Uiso 1 1 calc R U . . .
H32B H -0.644889 0.507397 0.247334 0.071 Uiso 1 1 calc R U . . .
H32C H -0.705913 0.615431 0.210071 0.071 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O6 1.911(3) . ?
Cu1 O5 1.916(3) . ?
Cu1 N2 1.954(4) . ?
Cu1 N1 1.960(4) . ?
Cu1 Cu2 2.9085(8) . ?
Cu2 O5 1.915(3) . ?
Cu2 O6 1.934(3) . ?
Cu2 N4 1.959(4) . ?
Cu2 N3 1.967(4) . ?
O1 C1 1.326(6) . ?
O1 H1O 0.8200 . ?
O2 C1 1.227(6) . ?
O3 C8 1.156(9) . ?
O4 C8 1.272(9) . ?
O4 H4O 0.8200 . ?
O5 C3 1.329(5) . ?
O6 C9 1.330(5) . ?
O7 N5 1.253(6) . ?
O8 N5 1.284(5) . ?
O9 N5 1.232(6) . ?
O10 N6 1.276(6) . ?
O11 N6 1.248(7) . ?
O12 N6 1.241(7) . ?
O13 C31 1.412(6) . ?
O13 H13O 0.8200 . ?
O14 C32 1.349(9) . ?
O14 H14 0.8202 . ?
N1 C15 1.465(6) . ?
N1 C19 1.499(5) . ?
N1 H1 1.0000 . ?
N2 C18 1.427(6) . ?
N2 C24 1.475(6) . ?
N2 H2 1.0000 . ?
N3 C16 1.487(6) . ?
N3 C25 1.514(5) . ?
N3 H3 1.0000 . ?
N4 C17 1.457(6) . ?
N4 C30 1.485(7) . ?
N4 H4 1.0000 . ?
C1 C6 1.478(6) . ?
C2 C7 1.400(6) . ?
C2 C3 1.404(6) . ?
C2 C16 1.520(6) . ?
C3 C4 1.422(6) . ?
C4 C5 1.382(6) . ?
C4 C15 1.511(5) . ?
C5 C6 1.403(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.398(7) . ?
C7 H7 0.9500 . ?
C8 C12 1.493(7) . ?
C9 C14 1.403(7) . ?
C9 C10 1.411(7) . ?
C10 C11 1.393(6) . ?
C10 C17 1.513(8) . ?
C11 C12 1.359(8) . ?
C11 H11 0.9500 . ?
C12 C13 1.382(8) . ?
C13 C14 1.394(6) . ?
C13 H13 0.9500 . ?
C14 C18 1.487(7) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.509(7) . ?
C19 C24 1.538(6) . ?
C19 H19 1.0000 . ?
C20 C21 1.531(6) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.527(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.530(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.543(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24 1.0000 . ?
C25 C26 1.516(7) . ?
C25 C30 1.538(6) . ?
C25 H25 1.0000 . ?
C26 C27 1.530(6) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.518(7) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.507(7) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.525(7) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?

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
O6 Cu1 O5 81.75(13) . . ?
O6 Cu1 N2 93.58(16) . . ?
O5 Cu1 N2 174.31(19) . . ?
O6 Cu1 N1 173.99(17) . . ?
O5 Cu1 N1 94.64(14) . . ?
N2 Cu1 N1 89.74(17) . . ?
O6 Cu1 Cu2 41.14(9) . . ?
O5 Cu1 Cu2 40.61(10) . . ?
N2 Cu1 Cu2 134.66(14) . . ?
N1 Cu1 Cu2 135.09(11) . . ?
O5 Cu2 O6 81.18(13) . . ?
O5 Cu2 N4 167.49(18) . . ?
O6 Cu2 N4 94.11(16) . . ?
O5 Cu2 N3 95.33(15) . . ?
O6 Cu2 N3 174.68(15) . . ?
N4 Cu2 N3 90.11(17) . . ?
O5 Cu2 Cu1 40.62(9) . . ?
O6 Cu2 Cu1 40.56(10) . . ?
N4 Cu2 Cu1 133.50(13) . . ?
N3 Cu2 Cu1 135.86(12) . . ?
C1 O1 H1O 109.6 . . ?
C8 O4 H4O 109.2 . . ?
C3 O5 Cu2 129.5(3) . . ?
C3 O5 Cu1 130.5(3) . . ?
Cu2 O5 Cu1 98.77(14) . . ?
C9 O6 Cu1 129.5(3) . . ?
C9 O6 Cu2 129.7(3) . . ?
Cu1 O6 Cu2 98.30(14) . . ?
C31 O13 H13O 109.5 . . ?
C32 O14 H14 108.5 . . ?
C15 N1 C19 113.9(3) . . ?
C15 N1 Cu1 111.2(3) . . ?
C19 N1 Cu1 105.0(3) . . ?
C15 N1 H1 108.8 . . ?
C19 N1 H1 108.8 . . ?
Cu1 N1 H1 108.8 . . ?
C18 N2 C24 116.7(4) . . ?
C18 N2 Cu1 113.1(3) . . ?
C24 N2 Cu1 106.1(3) . . ?
C18 N2 H2 106.8 . . ?
C24 N2 H2 106.8 . . ?
Cu1 N2 H2 106.8 . . ?
C16 N3 C25 114.0(3) . . ?
C16 N3 Cu2 111.3(3) . . ?
C25 N3 Cu2 103.9(3) . . ?
C16 N3 H3 109.2 . . ?
C25 N3 H3 109.2 . . ?
Cu2 N3 H3 109.2 . . ?
C17 N4 C30 116.7(4) . . ?
C17 N4 Cu2 113.1(3) . . ?
C30 N4 Cu2 104.6(3) . . ?
C17 N4 H4 107.3 . . ?
C30 N4 H4 107.3 . . ?
Cu2 N4 H4 107.3 . . ?
O9 N5 O7 121.8(4) . . ?
O9 N5 O8 119.4(4) . . ?
O7 N5 O8 118.9(4) . . ?
O12 N6 O11 121.5(5) . . ?
O12 N6 O10 117.9(5) . . ?
O11 N6 O10 120.7(5) . . ?
O2 C1 O1 122.5(4) . . ?
O2 C1 C6 123.0(4) . . ?
O1 C1 C6 114.5(4) . . ?
C7 C2 C3 118.7(4) . . ?
C7 C2 C16 119.3(4) . . ?
C3 C2 C16 121.8(4) . . ?
O5 C3 C2 119.6(4) . . ?
O5 C3 C4 119.5(4) . . ?
C2 C3 C4 120.9(4) . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 C15 118.4(4) . . ?
C3 C4 C15 122.6(4) . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 119.4(4) . . ?
C7 C6 C1 122.3(4) . . ?
C5 C6 C1 118.3(4) . . ?
C6 C7 C2 120.9(4) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
O3 C8 O4 120.1(6) . . ?
O3 C8 C12 124.0(7) . . ?
O4 C8 C12 115.4(6) . . ?
O6 C9 C14 120.0(4) . . ?
O6 C9 C10 119.7(4) . . ?
C14 C9 C10 120.3(4) . . ?
C11 C10 C9 118.3(5) . . ?
C11 C10 C17 119.6(5) . . ?
C9 C10 C17 121.8(4) . . ?
C12 C11 C10 121.4(5) . . ?
C12 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?
C11 C12 C13 120.5(4) . . ?
C11 C12 C8 117.3(5) . . ?
C13 C12 C8 122.2(5) . . ?
C12 C13 C14 120.6(5) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C13 C14 C9 118.7(4) . . ?
C13 C14 C18 116.3(4) . . ?
C9 C14 C18 124.7(4) . . ?
N1 C15 C4 115.7(3) . . ?
N1 C15 H15A 108.4 . . ?
C4 C15 H15A 108.4 . . ?
N1 C15 H15B 108.4 . . ?
C4 C15 H15B 108.4 . . ?
H15A C15 H15B 107.4 . . ?
N3 C16 C2 115.3(3) . . ?
N3 C16 H16A 108.4 . . ?
C2 C16 H16A 108.4 . . ?
N3 C16 H16B 108.4 . . ?
C2 C16 H16B 108.4 . . ?
H16A C16 H16B 107.5 . . ?
N4 C17 C10 115.2(5) . . ?
N4 C17 H17A 108.5 . . ?
C10 C17 H17A 108.5 . . ?
N4 C17 H17B 108.5 . . ?
C10 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
N2 C18 C14 118.2(4) . . ?
N2 C18 H18A 107.8 . . ?
C14 C18 H18A 107.8 . . ?
N2 C18 H18B 107.8 . . ?
C14 C18 H18B 107.8 . . ?
H18A C18 H18B 107.1 . . ?
N1 C19 C20 113.4(4) . . ?
N1 C19 C24 107.7(3) . . ?
C20 C19 C24 111.1(4) . . ?
N1 C19 H19 108.2 . . ?
C20 C19 H19 108.2 . . ?
C24 C19 H19 108.2 . . ?
C19 C20 C21 111.4(4) . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20B 109.3 . . ?
C21 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 111.2(4) . . ?
C22 C21 H21A 109.4 . . ?
C20 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C20 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 C23 111.0(4) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 110.3(4) . . ?
C22 C23 H23A 109.6 . . ?
C24 C23 H23A 109.6 . . ?
C22 C23 H23B 109.6 . . ?
C24 C23 H23B 109.6 . . ?
H23A C23 H23B 108.1 . . ?
N2 C24 C19 107.5(4) . . ?
N2 C24 C23 113.4(4) . . ?
C19 C24 C23 110.6(4) . . ?
N2 C24 H24 108.4 . . ?
C19 C24 H24 108.4 . . ?
C23 C24 H24 108.4 . . ?
N3 C25 C26 113.0(4) . . ?
N3 C25 C30 106.4(3) . . ?
C26 C25 C30 112.4(4) . . ?
N3 C25 H25 108.3 . . ?
C26 C25 H25 108.3 . . ?
C30 C25 H25 108.3 . . ?
C25 C26 C27 110.9(4) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 111.4(4) . . ?
C28 C27 H27A 109.3 . . ?
C26 C27 H27A 109.3 . . ?
C28 C27 H27B 109.3 . . ?
C26 C27 H27B 109.3 . . ?
H27A C27 H27B 108.0 . . ?
C29 C28 C27 111.4(4) . . ?
C29 C28 H28A 109.3 . . ?
C27 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C27 C28 H28B 109.3 . . ?
H28A C28 H28B 108.0 . . ?
C28 C29 C30 111.3(4) . . ?
C28 C29 H29A 109.4 . . ?
C30 C29 H29A 109.4 . . ?
C28 C29 H29B 109.4 . . ?
C30 C29 H29B 109.4 . . ?
H29A C29 H29B 108.0 . . ?
N4 C30 C29 113.6(4) . . ?
N4 C30 C25 106.7(4) . . ?
C29 C30 C25 111.9(4) . . ?
N4 C30 H30 108.2 . . ?
C29 C30 H30 108.2 . . ?
C25 C30 H30 108.2 . . ?
O13 C31 H31A 109.5 . . ?
O13 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O13 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
O14 C32 H32A 109.5 . . ?
O14 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
O14 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O13 0.82 1.80 2.615(4) 177.1 .
O4 H4O O14 0.82 1.93 2.729(7) 165.6 .
O13 H13O O8 0.82 2.00 2.729(5) 148.2 2_747
O14 H14 O10 0.82 1.89 2.709(8) 172.9 2_556
O14 H14 N6 0.82 2.70 3.480(8) 160.6 2_556
N3 H3 O2 1.00 2.10 3.058(6) 159.6 2_757

_refine_diff_density_max         0.660
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_rac-ligand
_database_code_depnum_ccdc_archive 'CCDC 1822397'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 Cu2 N6 O12, 2(C H4 O)'
_chemical_formula_sum            'C32 H38 Cu2 N6 O14'
_chemical_formula_weight         857.76

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'

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

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

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

_cell_length_a                   8.70380(10)
_cell_length_b                   13.4115(2)
_cell_length_c                   15.6432(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.055(2)
_cell_angle_gamma                90
_cell_volume                     1778.85(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    99.9(5)
_cell_measurement_reflns_used    4216
_cell_measurement_theta_min      3.2550
_cell_measurement_theta_max      72.7860

_exptl_crystal_description       needle
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             884
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    2.151
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61844
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      99.9(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            6962
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0178
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         5.217
_diffrn_reflns_theta_max         73.111
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3480
_reflns_number_gt                3182
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+1.8072P] 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         3480
_refine_ls_number_parameters     330
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.087
_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 -0.08365(3) 0.42106(2) 0.53152(2) 0.02437(11) Uani 1 1 d . . . . .
O1 O 0.77733(18) 0.44590(12) 0.81910(11) 0.0336(4) Uani 1 1 d . . . . .
H1A H 0.864406 0.421307 0.861937 0.040 Uiso 1 1 calc R U . . .
O2 O 0.65475(19) 0.31652(14) 0.86313(12) 0.0427(4) Uani 1 1 d . . . . .
O3 O 0.12026(19) 0.47975(14) 0.55554(12) 0.0509(6) Uani 1 1 d . . . . .
O6 O -0.2255(2) 0.70479(15) 0.63288(12) 0.0428(4) Uani 1 1 d . . . . .
O7 O 1.0077(2) 0.37376(13) 0.93898(13) 0.0434(4) Uani 1 1 d . . . . .
H7A H 1.019390 0.305638 0.925040 0.052 Uiso 1 1 calc R U . . .
N1 N 0.28920(19) 0.63271(12) 0.50029(11) 0.0232(4) Uani 1 1 d . . . . .
N2 N -0.0317(2) 0.32676(18) 0.62266(14) 0.0461(6) Uani 1 1 d . . . . .
C1 C 0.6543(2) 0.38741(16) 0.81567(13) 0.0246(4) Uani 1 1 d . . . . .
C2 C 0.5140(2) 0.41527(15) 0.74575(13) 0.0207(4) Uani 1 1 d . . . . .
C3 C 0.5179(2) 0.49267(15) 0.68659(12) 0.0201(4) Uani 1 1 d . . . . .
H3 H 0.610228 0.529097 0.690943 0.024 Uiso 1 1 calc R U . . .
C4 C 0.3852(2) 0.51629(15) 0.62095(12) 0.0206(4) Uani 1 1 d . . . . .
C5 C 0.2451(2) 0.45956(16) 0.61538(13) 0.0259(4) Uani 1 1 d . . . . .
C6 C 0.2413(2) 0.38058(16) 0.67577(13) 0.0252(4) Uani 1 1 d . . . . .
C7 C 0.3771(2) 0.36040(15) 0.73990(13) 0.0225(4) Uani 1 1 d . . . . .
H7 H 0.375788 0.309011 0.779651 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1018(3) 0.3193(2) 0.67646(17) 0.0409(6) Uani 1 1 d . . . . .
H8 H 0.111587 0.270790 0.719874 0.049 Uiso 1 1 calc R U . . .
C9 C 0.3983(2) 0.60119(16) 0.56347(14) 0.0254(4) Uani 1 1 d . . . . .
H9 H 0.494225 0.634795 0.574006 0.030 Uiso 1 1 calc R U . . .
C16 C 1.1552(4) 0.4167(3) 0.9673(4) 0.0990(15) Uani 1 1 d . U . . .
H16A H 1.143386 0.485363 0.981811 0.149 Uiso 1 1 calc R U . . .
H16B H 1.211950 0.412515 0.921427 0.149 Uiso 1 1 calc R U . . .
H16C H 1.212474 0.381868 1.018201 0.149 Uiso 1 1 calc R U . . .
O4A O -0.1338(5) 0.5483(2) 0.6378(2) 0.0393(10) Uani 0.651(7) 1 d . . P A 1
O5A O -0.0064(4) 0.6704(2) 0.5932(2) 0.0308(8) Uani 0.651(7) 1 d . . P A 1
N3A N -0.1248(6) 0.6386(4) 0.6204(3) 0.0288(9) Uani 0.651(7) 1 d . . P A 1
C10A C 0.2891(4) 0.7292(3) 0.4558(3) 0.0181(8) Uani 0.644(7) 1 d . . P B 1
H10A H 0.240360 0.778773 0.487359 0.022 Uiso 0.644(7) 1 calc R U P B 1
C11A C 0.4490(15) 0.7661(9) 0.4515(8) 0.022(2) Uani 0.644(7) 1 d . U P B 1
H11A H 0.499722 0.718554 0.420109 0.027 Uiso 0.644(7) 1 calc R U P B 1
H11B H 0.513860 0.773592 0.510308 0.027 Uiso 0.644(7) 1 calc R U P B 1
C12A C 0.4318(4) 0.8691(3) 0.4030(3) 0.0286(9) Uani 0.644(7) 1 d . . P B 1
H12A H 0.392462 0.918184 0.438304 0.034 Uiso 0.644(7) 1 calc R U P B 1
H12B H 0.534582 0.891037 0.396278 0.034 Uiso 0.644(7) 1 calc R U P B 1
C13A C 0.3199(5) 0.8624(4) 0.3131(3) 0.0311(10) Uani 0.644(7) 1 d . . P B 1
H13A H 0.369446 0.823277 0.274687 0.037 Uiso 0.644(7) 1 calc R U P B 1
H13B H 0.302331 0.928949 0.288546 0.037 Uiso 0.644(7) 1 calc R U P B 1
C14A C 0.1611(11) 0.8158(7) 0.3151(6) 0.0240(17) Uani 0.644(7) 1 d . U P B 1
H14A H 0.101907 0.860844 0.344048 0.029 Uiso 0.644(7) 1 calc R U P B 1
H14B H 0.101066 0.805462 0.255497 0.029 Uiso 0.644(7) 1 calc R U P B 1
C15A C 0.1837(4) 0.7170(3) 0.3633(2) 0.0209(9) Uani 0.644(7) 1 d . . P B 1
H15A H 0.233095 0.669503 0.330165 0.025 Uiso 0.644(7) 1 calc R U P B 1
C10B C 0.3088(8) 0.7012(5) 0.4225(5) 0.0196(14) Uani 0.356(7) 1 d . . P B 2
H10B H 0.311224 0.658852 0.371764 0.024 Uiso 0.356(7) 1 calc R U P B 2
C11B C 0.457(3) 0.7719(17) 0.4392(13) 0.019(3) Uani 0.356(7) 1 d . U P B 2
H11C H 0.461582 0.811176 0.491733 0.023 Uiso 0.356(7) 1 calc R U P B 2
H11D H 0.552934 0.732265 0.447828 0.023 Uiso 0.356(7) 1 calc R U P B 2
C12B C 0.4473(8) 0.8385(6) 0.3633(6) 0.0272(16) Uani 0.356(7) 1 d . . P B 2
H12C H 0.453025 0.798900 0.312206 0.033 Uiso 0.356(7) 1 calc R U P B 2
H12D H 0.536840 0.883529 0.374889 0.033 Uiso 0.356(7) 1 calc R U P B 2
C13B C 0.2960(8) 0.8991(6) 0.3434(5) 0.0254(16) Uani 0.356(7) 1 d . . P B 2
H13C H 0.293893 0.940154 0.292092 0.031 Uiso 0.356(7) 1 calc R U P B 2
H13D H 0.295085 0.943279 0.392410 0.031 Uiso 0.356(7) 1 calc R U P B 2
C14B C 0.149(2) 0.8343(12) 0.3269(11) 0.021(3) Uani 0.356(7) 1 d . U P B 2
H14C H 0.055991 0.876256 0.320626 0.025 Uiso 0.356(7) 1 calc R U P B 2
H14D H 0.140190 0.797332 0.272732 0.025 Uiso 0.356(7) 1 calc R U P B 2
C15B C 0.1555(6) 0.7628(5) 0.4016(4) 0.0206(16) Uani 0.356(7) 1 d . . P B 2
H15B H 0.140775 0.798167 0.453953 0.025 Uiso 0.356(7) 1 calc R U P B 2
O4B O -0.2180(7) 0.5671(3) 0.5855(5) 0.0350(19) Uani 0.349(7) 1 d . . P A 3
O5B O -0.0786(8) 0.6856(4) 0.5422(5) 0.0359(19) Uani 0.349(7) 1 d . . P A 3
N3B N -0.1741(11) 0.6564(6) 0.5889(6) 0.0266(16) Uani 0.349(7) 1 d . . P A 3


_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 1.8788(16) 3_566 ?
Cu1 N2 1.8830(19) . ?
Cu1 N1 1.8885(17) 3_566 ?
Cu1 O3 1.8998(16) . ?
Cu1 Cu1 2.8679(6) 3_566 ?
O1 C1 1.319(3) . ?
O1 H1A 0.9501 . ?
O2 C1 1.206(3) . ?
O3 C5 1.292(3) . ?
O6 N3B 1.111(8) . ?
O6 N3A 1.294(5) . ?
O7 C16 1.385(4) . ?
O7 H7A 0.9501 . ?
N1 C9 1.278(3) . ?
N1 C10A 1.470(4) . ?
N1 C10B 1.565(6) . ?
N2 C8 1.275(3) . ?
N2 C15A 1.509(3) 3_566 ?
N2 C15B 1.602(6) 3_566 ?
C1 C2 1.491(3) . ?
C2 C7 1.386(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.423(3) . ?
C4 C9 1.471(3) . ?
C5 C6 1.425(3) . ?
C6 C7 1.393(3) . ?
C6 C8 1.469(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
O4A N3A 1.248(5) . ?
O5A N3A 1.273(5) . ?
C10A C11A 1.493(14) . ?
C10A C15A 1.536(5) . ?
C10A H10A 0.9800 . ?
C11A C12A 1.566(13) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13A 1.522(6) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C13A C14A 1.523(11) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C14A C15A 1.516(10) . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C15A H15A 0.9800 . ?
C10B C15B 1.540(10) . ?
C10B C11B 1.58(2) . ?
C10B H10B 0.9800 . ?
C11B C12B 1.47(2) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C13B 1.520(11) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C13B C14B 1.52(2) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C14B C15B 1.501(19) . ?
C14B H14C 0.9700 . ?
C14B H14D 0.9700 . ?
C15B H15B 0.9800 . ?
O4B N3B 1.255(9) . ?
O5B N3B 1.286(9) . ?

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 N2 175.43(8) 3_566 . ?
O3 Cu1 N1 94.82(7) 3_566 3_566 ?
N2 Cu1 N1 89.68(8) . 3_566 ?
O3 Cu1 O3 81.25(7) 3_566 . ?
N2 Cu1 O3 94.27(8) . . ?
N1 Cu1 O3 175.89(7) 3_566 . ?
O3 Cu1 Cu1 40.90(5) 3_566 3_566 ?
N2 Cu1 Cu1 134.62(6) . 3_566 ?
N1 Cu1 Cu1 135.70(5) 3_566 3_566 ?
O3 Cu1 Cu1 40.35(5) . 3_566 ?
C1 O1 H1A 109.5 . . ?
C5 O3 Cu1 130.58(14) . 3_566 ?
C5 O3 Cu1 130.64(14) . . ?
Cu1 O3 Cu1 98.75(7) 3_566 . ?
C16 O7 H7A 109.5 . . ?
C9 N1 C10A 125.3(2) . . ?
C9 N1 C10B 127.1(3) . . ?
C9 N1 Cu1 124.87(14) . 3_566 ?
C10A N1 Cu1 108.21(16) . 3_566 ?
C8 N2 C15A 124.9(2) . 3_566 ?
C8 N2 C15B 124.1(3) . 3_566 ?
C15A N2 C15B 34.6(2) 3_566 3_566 ?
C8 N2 Cu1 125.46(16) . . ?
C15A N2 Cu1 107.61(16) 3_566 . ?
C15B N2 Cu1 106.9(2) 3_566 . ?
O2 C1 O1 123.66(19) . . ?
O2 C1 C2 122.52(19) . . ?
O1 C1 C2 113.81(18) . . ?
C7 C2 C3 120.01(18) . . ?
C7 C2 C1 117.70(18) . . ?
C3 C2 C1 122.29(18) . . ?
C2 C3 C4 121.07(18) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.57(18) . . ?
C3 C4 C9 117.34(17) . . ?
C5 C4 C9 124.06(18) . . ?
O3 C5 C4 120.05(18) . . ?
O3 C5 C6 119.65(18) . . ?
C4 C5 C6 120.30(18) . . ?
C7 C6 C5 118.63(18) . . ?
C7 C6 C8 117.02(18) . . ?
C5 C6 C8 124.34(19) . . ?
C2 C7 C6 121.42(18) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
N2 C8 C6 125.6(2) . . ?
N2 C8 H8 117.2 . . ?
C6 C8 H8 117.2 . . ?
N1 C9 C4 125.58(18) . . ?
N1 C9 H9 117.2 . . ?
C4 C9 H9 117.2 . . ?
O7 C16 H16A 109.5 . . ?
O7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4A N3A O5A 119.6(4) . . ?
O4A N3A O6 123.7(4) . . ?
O5A N3A O6 116.6(4) . . ?
N1 C10A C11A 114.4(5) . . ?
N1 C10A C15A 106.7(3) . . ?
C11A C10A C15A 110.9(5) . . ?
N1 C10A H10A 108.2 . . ?
C11A C10A H10A 108.2 . . ?
C15A C10A H10A 108.2 . . ?
C10A C11A C12A 109.0(8) . . ?
C10A C11A H11A 109.9 . . ?
C12A C11A H11A 109.9 . . ?
C10A C11A H11B 109.9 . . ?
C12A C11A H11B 109.9 . . ?
H11A C11A H11B 108.3 . . ?
C13A C12A C11A 111.5(6) . . ?
C13A C12A H12A 109.3 . . ?
C11A C12A H12A 109.3 . . ?
C13A C12A H12B 109.3 . . ?
C11A C12A H12B 109.3 . . ?
H12A C12A H12B 108.0 . . ?
C12A C13A C14A 113.6(5) . . ?
C12A C13A H13A 108.8 . . ?
C14A C13A H13A 108.8 . . ?
C12A C13A H13B 108.8 . . ?
C14A C13A H13B 108.8 . . ?
H13A C13A H13B 107.7 . . ?
C15A C14A C13A 110.6(6) . . ?
C15A C14A H14A 109.5 . . ?
C13A C14A H14A 109.5 . . ?
C15A C14A H14B 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 108.1 . . ?
N2 C15A C14A 113.1(4) 3_566 . ?
N2 C15A C10A 105.2(3) 3_566 . ?
C14A C15A C10A 111.0(4) . . ?
N2 C15A H15A 109.1 3_566 . ?
C14A C15A H15A 109.1 . . ?
C10A C15A H15A 109.1 . . ?
C15B C10B N1 103.8(5) . . ?
C15B C10B C11B 110.6(10) . . ?
N1 C10B C11B 117.0(8) . . ?
C15B C10B H10B 108.4 . . ?
N1 C10B H10B 108.4 . . ?
C11B C10B H10B 108.4 . . ?
C12B C11B C10B 109.5(12) . . ?
C12B C11B H11C 109.8 . . ?
C10B C11B H11C 109.8 . . ?
C12B C11B H11D 109.8 . . ?
C10B C11B H11D 109.8 . . ?
H11C C11B H11D 108.2 . . ?
C11B C12B C13B 112.4(11) . . ?
C11B C12B H12C 109.1 . . ?
C13B C12B H12C 109.1 . . ?
C11B C12B H12D 109.1 . . ?
C13B C12B H12D 109.1 . . ?
H12C C12B H12D 107.9 . . ?
C12B C13B C14B 112.8(8) . . ?
C12B C13B H13C 109.0 . . ?
C14B C13B H13C 109.0 . . ?
C12B C13B H13D 109.0 . . ?
C14B C13B H13D 109.0 . . ?
H13C C13B H13D 107.8 . . ?
C15B C14B C13B 110.4(12) . . ?
C15B C14B H14C 109.6 . . ?
C13B C14B H14C 109.6 . . ?
C15B C14B H14D 109.6 . . ?
C13B C14B H14D 109.6 . . ?
H14C C14B H14D 108.1 . . ?
C14B C15B C10B 112.8(8) . . ?
C14B C15B H15B 110.6 . . ?
C10B C15B H15B 110.6 . . ?
N2 C15B H15B 110.6 3_566 . ?
O6 N3B O4B 115.0(7) . . ?
O6 N3B O5B 125.2(7) . . ?
O4B N3B O5B 119.7(7) . . ?

_refine_diff_density_max         0.464
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_FJI-Y6-Dye
_database_code_depnum_ccdc_archive 'CCDC 1822395'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C90 H84 Cu6 In3 N12 O22'
_chemical_formula_weight         2411.39

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'
In In 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           163
_space_group_name_H-M_alt        'P -3 1 c'
_space_group_name_Hall           '-P 3 2c'

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

_cell_length_a                   23.0639(3)
_cell_length_b                   23.0639(3)
_cell_length_c                   30.1054(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     13868.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9680
_cell_measurement_theta_min      3.68
_cell_measurement_theta_max      71.88

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.577
_exptl_crystal_F_000             2410
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    2.664
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3753
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            101698
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.677
_diffrn_reflns_theta_max         72.412
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9058
_reflns_number_gt                7505
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1300P)²+8.9100P] 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         9058
_refine_ls_number_parameters     342
_refine_ls_number_restraints     226
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1957
_refine_ls_wR_factor_gt          0.1815
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.260
_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
C1 C 0.6724(3) 0.9982(4) 0.5266(2) 0.087(3) Uani 0.5 1 d DG U P A -1
H1 H 0.652880 0.950918 0.534664 0.105 Uiso 0.5 1 calc R U P A -1
C2 C 0.7455(4) 1.0324(5) 0.5454(3) 0.094(3) Uani 0.5 1 d G U P A -1
H2A H 0.743872 1.028411 0.577495 0.113 Uiso 0.5 1 calc R U P A -1
H2B H 0.768593 1.079714 0.538025 0.113 Uiso 0.5 1 calc R U P A -1
C3 C 0.7855(4) 0.9998(5) 0.5259(2) 0.105(3) Uani 0.5 1 d G U P A -1
H3A H 0.765760 0.954054 0.536493 0.126 Uiso 0.5 1 calc R U P A -1
H3B H 0.831378 1.024273 0.536444 0.126 Uiso 0.5 1 calc R U P A -1
C4 C 0.7851(4) 1.0000(5) 0.4739(3) 0.103(3) Uani 0.5 1 d G U P A -1
H4A H 0.809976 1.045797 0.463280 0.124 Uiso 0.5 1 calc R U P A -1
H4B H 0.807277 0.976450 0.462986 0.124 Uiso 0.5 1 calc R U P A -1
C5 C 0.7120(4) 0.9658(5) 0.4551(3) 0.111(5) Uani 0.5 1 d G U P A -1
H5A H 0.688965 0.918486 0.462429 0.133 Uiso 0.5 1 calc R U P A -1
H5B H 0.713686 0.969789 0.422959 0.133 Uiso 0.5 1 calc R U P A -1
C6 C 0.6720(3) 0.9984(4) 0.4745(3) 0.090(3) Uani 0.5 1 d DG U P A -1
H6 H 0.684482 1.042052 0.461507 0.108 Uiso 0.5 1 calc R U P A -1
C7 C 0.3450(4) 1.0341(5) 0.5100(3) 0.119(4) Uani 0.5 1 d DG U P A -1
H7 H 0.372389 1.066034 0.486859 0.142 Uiso 0.5 1 calc R U P A -1
C8 C 0.2983(5) 1.0530(6) 0.5354(3) 0.121(6) Uani 0.5 1 d G U P A -1
H8A H 0.322721 1.100373 0.542470 0.145 Uiso 0.5 1 calc R U P A -1
H8B H 0.284289 1.028252 0.563062 0.145 Uiso 0.5 1 calc R U P A -1
C9 C 0.2355(5) 1.0373(5) 0.5075(4) 0.122(4) Uani 0.5 1 d G U P A -1
H9A H 0.205771 1.046502 0.525110 0.146 Uiso 0.5 1 calc R U P A -1
H9B H 0.249050 1.066326 0.481632 0.146 Uiso 0.5 1 calc R U P A -1
C10 C 0.1973(5) 0.9631(5) 0.4921(4) 0.134(5) Uani 0.5 1 d G U P A -1
H10A H 0.178711 0.934256 0.517810 0.161 Uiso 0.5 1 calc R U P A -1
H10B H 0.160470 0.955926 0.472933 0.161 Uiso 0.5 1 calc R U P A -1
C11 C 0.2441(5) 0.9442(6) 0.4667(3) 0.122(5) Uani 0.5 1 d G U P A -1
H11A H 0.258042 0.968929 0.438992 0.146 Uiso 0.5 1 calc R U P A -1
H11B H 0.219610 0.896808 0.459584 0.146 Uiso 0.5 1 calc R U P A -1
C12 C 0.3069(5) 0.9599(5) 0.4946(3) 0.112(4) Uani 0.5 1 d DG U P A -1
H12 H 0.290125 0.932946 0.521691 0.134 Uiso 0.5 1 calc R U P A -1
In1 In 0.43562(2) 0.71781(2) 0.250000 0.04272(14) Uani 1 2 d S T P . .
C13 C 0.4016(2) 0.8030(2) 0.31648(14) 0.0667(10) Uani 1 1 d . U . . .
O3 O 0.34452(15) 0.78659(15) 0.30160(9) 0.0729(8) Uani 1 1 d . . . . .
O4 O 0.44198(14) 0.78640(15) 0.30174(9) 0.0733(8) Uani 1 1 d . . . . .
O5 O 0.333333 0.666667 0.250000 0.0459(11) Uani 1 6 d S T P . .
O6 O 0.54999(18) 0.77499(9) 0.250000 0.0697(10) Uani 1 2 d S T P . .
Cu1 Cu 0.42070(11) 0.96532(16) 0.51691(8) 0.1447(10) Uani 0.5 1 d . U P A -1
Cu2 Cu 0.54493(11) 0.96646(16) 0.51646(8) 0.1473(10) Uani 0.5 1 d . U P A -1
O1 O 0.4643(4) 0.9291(4) 0.4833(3) 0.106(2) Uani 0.5 1 d . U P A -1
O2 O 0.5019(4) 1.0037(4) 0.5492(3) 0.110(2) Uani 0.5 1 d . U P A -1
N1 N 0.3522(5) 0.9418(6) 0.4747(3) 0.096(3) Uani 0.5 1 d D U P A -1
N2 N 0.5941(4) 0.9469(5) 0.4737(4) 0.098(3) Uani 0.5 1 d D U P A -1
N3 N 0.3860(5) 1.0174(5) 0.5448(3) 0.097(3) Uani 0.5 1 d D U P A -1
N4 N 0.6281(4) 1.0181(5) 0.5457(3) 0.090(2) Uani 0.5 1 d D U P A -1
C14 C 0.4160(6) 0.8348(6) 0.3617(4) 0.066(3) Uani 0.5 1 d . U P A -1
C15 C 0.3755(5) 0.8547(5) 0.3816(4) 0.071(3) Uani 0.5 1 d . U P A -1
H15 H 0.335354 0.844404 0.367809 0.085 Uiso 0.5 1 calc R U P A -1
C16 C 0.3917(5) 0.8900(6) 0.4218(4) 0.080(2) Uani 0.5 1 d . U P A -1
C17 C 0.4521(5) 0.9046(6) 0.4424(4) 0.085(3) Uani 0.5 1 d . U P A -1
C18 C 0.4978(5) 0.8900(6) 0.4218(4) 0.082(3) Uani 0.5 1 d . U P A -1
C19 C 0.4777(6) 0.8547(5) 0.3819(4) 0.072(3) Uani 0.5 1 d . U P A -1
H19 H 0.506963 0.843843 0.367990 0.087 Uiso 0.5 1 calc R U P A -1
C20 C 0.3432(6) 0.9044(7) 0.4411(4) 0.097(3) Uani 0.5 1 d . U P A -1
H20 H 0.301181 0.884423 0.427824 0.116 Uiso 0.5 1 calc R U P A -1
C21 C 0.5617(6) 0.9068(6) 0.4401(4) 0.092(3) Uani 0.5 1 d . U P A -1
H21 H 0.583267 0.886560 0.426543 0.111 Uiso 0.5 1 calc R U P A -1
C22 C 0.6395(5) 1.0582(5) 0.5778(3) 0.077(2) Uani 0.5 1 d . U P A -1
H22 H 0.682253 1.079183 0.590038 0.093 Uiso 0.5 1 calc R U P A -1
C23 C 0.4178(5) 1.0562(5) 0.5786(3) 0.078(2) Uani 0.5 1 d . U P A -1
H23 H 0.395536 1.075168 0.592889 0.093 Uiso 0.5 1 calc R U P A -1
C24 C 0.5903(5) 1.0741(5) 0.5972(3) 0.077(2) Uani 0.5 1 d . U P A -1
C25 C 0.5248(5) 1.0496(5) 0.5808(3) 0.083(2) Uani 0.5 1 d . U P A -1
C26 C 0.4837(5) 1.0740(5) 0.5971(3) 0.075(2) Uani 0.5 1 d . U P A -1
C27 C 0.5075(5) 1.1191(5) 0.6318(3) 0.065(2) Uani 0.5 1 d . U P A -1
H27 H 0.480324 1.134030 0.644058 0.078 Uiso 0.5 1 calc R U P A -1
C28 C 0.5703(5) 1.1422(5) 0.6483(3) 0.056(2) Uani 0.5 1 d . U P A -1
C29 C 0.6106(5) 1.1193(5) 0.6318(3) 0.065(2) Uani 0.5 1 d . U P A -1
H29 H 0.652734 1.134714 0.644192 0.077 Uiso 0.5 1 calc R U P A -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N4 1.434(7) . ?
C1 C2 1.567(5) . ?
C1 C6 1.567(5) . ?
C2 C3 1.567(5) . ?
C3 C4 1.567(5) . ?
C4 C5 1.567(5) . ?
C5 C6 1.567(5) . ?
C6 N2 1.583(8) . ?
C7 C8 1.552(7) . ?
C7 C12 1.553(7) . ?
C7 N3 1.583(8) . ?
C8 C9 1.553(7) . ?
C9 C10 1.553(7) . ?
C10 C11 1.553(7) . ?
C11 C12 1.553(7) . ?
C12 N1 1.436(8) . ?
In1 O5 2.0432(3) . ?
In1 O3 2.171(2) 5 ?
In1 O3 2.171(2) 3_565 ?
In1 O4 2.172(2) . ?
In1 O4 2.172(2) 6_565 ?
In1 O6 2.284(4) . ?
C13 O4 1.251(5) . ?
C13 O3 1.257(5) . ?
C13 C14 1.503(12) . ?
Cu1 N1 1.884(10) . ?
Cu1 O1 1.891(7) . ?
Cu1 O2 1.893(7) . ?
Cu1 N3 1.936(10) . ?
Cu1 Cu2 2.852(2) . ?
Cu2 O2 1.883(7) . ?
Cu2 N4 1.894(9) . ?
Cu2 O1 1.896(7) . ?
Cu2 N2 1.913(10) . ?
O1 C17 1.324(11) . ?
O2 C25 1.320(10) . ?
N1 C20 1.278(14) . ?
N2 C21 1.321(14) . ?
N3 C23 1.310(12) . ?
N4 C22 1.272(11) . ?
C14 C15 1.369(17) . ?
C14 C19 1.398(16) . ?
C15 C16 1.400(14) . ?
C16 C17 1.406(14) . ?
C16 C20 1.437(15) . ?
C17 C18 1.402(14) . ?
C18 C19 1.392(14) . ?
C18 C21 1.434(15) . ?
C22 C24 1.476(13) . ?
C23 C26 1.472(13) . ?
C24 C29 1.379(12) . ?
C24 C25 1.411(13) . ?
C25 C26 1.412(13) . ?
C26 C27 1.379(12) . ?
C27 C28 1.361(14) . ?
C28 C29 1.372(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
N4 C1 C2 117.0(5) . . ?
N4 C1 C6 113.2(6) . . ?
C2 C1 C6 111.5 . . ?
C1 C2 C3 111.5 . . ?
C2 C3 C4 111.5 . . ?
C5 C4 C3 111.5 . . ?
C4 C5 C6 111.5 . . ?
C5 C6 C1 111.5 . . ?
C5 C6 N2 110.7(5) . . ?
C1 C6 N2 91.1(6) . . ?
C8 C7 C12 111.5 . . ?
C8 C7 N3 109.0(6) . . ?
C12 C7 N3 90.5(7) . . ?
C7 C8 C9 111.5 . . ?
C10 C9 C8 111.5 . . ?
C11 C10 C9 111.5 . . ?
C10 C11 C12 111.5 . . ?
N1 C12 C11 115.9(7) . . ?
N1 C12 C7 110.5(8) . . ?
C11 C12 C7 111.5 . . ?
O5 In1 O3 93.40(8) . 5 ?
O5 In1 O3 93.40(8) . 3_565 ?
O3 In1 O3 173.20(15) 5 3_565 ?
O5 In1 O4 93.35(8) . . ?
O3 In1 O4 91.48(13) 5 . ?
O3 In1 O4 88.12(13) 3_565 . ?
O5 In1 O4 93.35(8) . 6_565 ?
O3 In1 O4 88.12(13) 5 6_565 ?
O3 In1 O4 91.48(13) 3_565 6_565 ?
O4 In1 O4 173.30(15) . 6_565 ?
O5 In1 O6 180.0 . . ?
O3 In1 O6 86.60(8) 5 . ?
O3 In1 O6 86.60(8) 3_565 . ?
O4 In1 O6 86.65(8) . . ?
O4 In1 O6 86.65(8) 6_565 . ?
O4 C13 O3 127.6(3) . . ?
O4 C13 C14 117.0(6) . . ?
O3 C13 C14 114.3(6) . . ?
C13 O3 In1 133.3(2) . 2_665 ?
C13 O4 In1 133.4(2) . . ?
In1 O5 In1 120.0 2_665 . ?
In1 O5 In1 120.0 2_665 3_565 ?
In1 O5 In1 120.0 . 3_565 ?
N1 Cu1 O1 93.8(3) . . ?
N1 Cu1 O2 166.7(5) . . ?
O1 Cu1 O2 82.0(3) . . ?
N1 Cu1 N3 85.7(4) . . ?
O1 Cu1 N3 169.2(5) . . ?
O2 Cu1 N3 96.1(3) . . ?
N1 Cu1 Cu2 133.9(2) . . ?
O1 Cu1 Cu2 41.2(2) . . ?
O2 Cu1 Cu2 40.8(2) . . ?
N3 Cu1 Cu2 136.1(3) . . ?
O2 Cu2 N4 93.9(3) . . ?
O2 Cu2 O1 82.1(3) . . ?
N4 Cu2 O1 170.1(5) . . ?
O2 Cu2 N2 165.9(5) . . ?
N4 Cu2 N2 85.8(4) . . ?
O1 Cu2 N2 95.8(3) . . ?
O2 Cu2 Cu1 41.1(2) . . ?
N4 Cu2 Cu1 134.5(2) . . ?
O1 Cu2 Cu1 41.1(2) . . ?
N2 Cu2 Cu1 135.4(3) . . ?
C17 O1 Cu1 129.8(7) . . ?
C17 O1 Cu2 129.4(7) . . ?
Cu1 O1 Cu2 97.7(3) . . ?
C25 O2 Cu2 130.7(7) . . ?
C25 O2 Cu1 130.6(6) . . ?
Cu2 O2 Cu1 98.1(3) . . ?
C20 N1 C12 129.1(10) . . ?
C20 N1 Cu1 123.9(8) . . ?
C12 N1 Cu1 105.2(6) . . ?
C21 N2 C6 124.8(9) . . ?
C21 N2 Cu2 119.0(7) . . ?
C6 N2 Cu2 113.4(6) . . ?
C23 N3 C7 123.1(9) . . ?
C23 N3 Cu1 119.8(7) . . ?
C7 N3 Cu1 110.2(6) . . ?
C22 N4 C1 128.0(8) . . ?
C22 N4 Cu2 125.9(7) . . ?
C1 N4 Cu2 105.8(5) . . ?
C15 C14 C19 116.9(10) . . ?
C15 C14 C13 122.7(10) . . ?
C19 C14 C13 119.7(10) . . ?
C14 C15 C16 123.0(10) . . ?
C15 C16 C17 117.8(9) . . ?
C15 C16 C20 118.1(10) . . ?
C17 C16 C20 123.9(9) . . ?
O1 C17 C18 119.3(10) . . ?
O1 C17 C16 119.1(9) . . ?
C18 C17 C16 121.4(9) . . ?
C19 C18 C17 116.9(10) . . ?
C19 C18 C21 119.2(10) . . ?
C17 C18 C21 123.9(9) . . ?
C18 C19 C14 123.7(10) . . ?
N1 C20 C16 126.4(11) . . ?
N2 C21 C18 129.1(10) . . ?
N4 C22 C24 125.2(9) . . ?
N3 C23 C26 129.1(9) . . ?
C29 C24 C25 117.3(9) . . ?
C29 C24 C22 118.3(9) . . ?
C25 C24 C22 124.3(8) . . ?
O2 C25 C24 119.5(8) . . ?
O2 C25 C26 119.4(9) . . ?
C24 C25 C26 121.1(8) . . ?
C27 C26 C25 118.1(9) . . ?
C27 C26 C23 117.6(8) . . ?
C25 C26 C23 124.3(8) . . ?
C28 C27 C26 121.0(9) . . ?
C27 C28 C29 120.7(9) . . ?
C28 C29 C24 121.7(9) . . ?

_refine_diff_density_max         0.739
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.082



####################################################################### 
# 
# 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_rac-FJI-Y6
_database_code_depnum_ccdc_archive 'CCDC 1822396'
_audit_update_record             
;
2018-02-06 deposited with the CCDC.
2018-02-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 Cu In0.50 N3 O6.67'
_chemical_formula_weight         463.91

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'
In In 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           194
_space_group_name_H-M_alt        'P 63/m m c'
_space_group_name_Hall           '-P 6c 2c'

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

_cell_length_a                   22.8847(5)
_cell_length_b                   22.8847(5)
_cell_length_c                   30.1026(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     13652.9(7)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      3.6600
_cell_measurement_theta_max      73.2080

_exptl_crystal_description       block
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.677
_exptl_crystal_F_000             2782
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_absorpt_coefficient_mu    2.801
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.04628
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 10.5594
_diffrn_reflns_number            31829
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         4.462
_diffrn_reflns_theta_max         73.424
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4987
_reflns_number_gt                3962
_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       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1385P)²+1.7929P] 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         4987
_refine_ls_number_parameters     201
_refine_ls_number_restraints     162
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0604
_refine_ls_wR_factor_ref         0.1948
_refine_ls_wR_factor_gt          0.1780
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.216
_refine_ls_shift/su_max          0.003
_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
C1 C 0.3266(3) 0.3182(4) 0.4648(2) 0.204(9) Uani 0.5 1 d G U P . .
H1 H 0.345137 0.294143 0.448423 0.245 Uiso 0.5 1 calc R U P . .
C2 C 0.2532(4) 0.2833(4) 0.4528(3) 0.089(2) Uani 0.5 1 d G U P . .
H2A H 0.248667 0.287571 0.421087 0.107 Uiso 0.5 1 calc R U P . .
H2B H 0.231741 0.304877 0.468096 0.107 Uiso 0.5 1 calc R U P . .
C3 C 0.2183(4) 0.2100(4) 0.4650(3) 0.234(11) Uani 0.5 1 d G U P . .
H3A H 0.170470 0.189693 0.458956 0.280 Uiso 0.5 1 calc R U P . .
H3B H 0.235896 0.187206 0.446886 0.280 Uiso 0.5 1 calc R U P . .
C4 C 0.2283(4) 0.2004(3) 0.5131(3) 0.098(3) Uani 0.5 1 d G U P . .
H4A H 0.208129 0.152543 0.519350 0.118 Uiso 0.5 1 calc R U P . .
H4B H 0.205680 0.218035 0.531284 0.118 Uiso 0.5 1 calc R U P . .
C5 C 0.3017(4) 0.2354(3) 0.5251(3) 0.137(5) Uani 0.5 1 d G U P . .
H5A H 0.306290 0.231070 0.556779 0.165 Uiso 0.5 1 calc R U P . .
H5B H 0.323208 0.213819 0.509753 0.165 Uiso 0.5 1 calc R U P . .
C6 C 0.3365(3) 0.3087(3) 0.5129(2) 0.087(2) Uani 0.5 1 d G U P . .
H6 H 0.313894 0.328282 0.529710 0.104 Uiso 0.5 1 calc R U P . .
In1 In 0.71794(2) 0.43588(2) 0.750000 0.04779(18) Uani 1 4 d S T P . .
Cu1 Cu 0.45303(8) 0.42168(8) 0.48453(7) 0.1547(12) Uani 0.5 1 d . U P . .
O1 O 0.77163(13) 0.5433(3) 0.750000 0.0833(15) Uani 1 4 d S TU P . .
O2 O 0.666667 0.333333 0.750000 0.0506(14) Uani 1 12 d S TU P . .
O3 O 0.65520(14) 0.44267(14) 0.69910(9) 0.0761(7) Uani 1 1 d . U . . .
O4 O 0.5329(3) 0.4671(3) 0.5186(3) 0.110(3) Uani 0.5 2 d S TU P . .
O5 O 0.4991(3) 0.5009(3) 0.4505(3) 0.108(3) Uani 0.5 2 d S TU P . .
O6 O 0.8544(6) 0.6185(6) 0.8337(4) 0.317(5) Uani 1 1 d . U . . .
O7 O 0.8124(4) 0.6249(7) 0.8919(5) 0.259(5) Uani 1 2 d S TU P . .
N1 N 0.4084(5) 0.3483(4) 0.5245(3) 0.096(2) Uani 0.5 1 d . U P . .
N2 N 0.3704(4) 0.3890(4) 0.4541(3) 0.099(2) Uani 0.5 1 d . U P . .
N3 N 0.8092(4) 0.6185(8) 0.8522(6) 0.200(5) Uani 1 2 d S TU P . .
C7 C 0.59774(14) 0.40226(14) 0.68411(18) 0.0698(12) Uani 1 2 d S TU P . .
C8 C 0.57566(18) 0.42434(18) 0.6447(2) 0.0923(19) Uani 1 2 d S TU P . .
C9 C 0.5199(5) 0.3766(5) 0.6197(3) 0.071(2) Uani 0.5 1 d . U P . .
H9 H 0.493789 0.333241 0.630982 0.086 Uiso 0.5 1 calc R U P . .
C10 C 0.5021(5) 0.3921(5) 0.5780(3) 0.083(2) Uani 0.5 1 d . U P . .
C11 C 0.5470(4) 0.4530(4) 0.5583(5) 0.089(3) Uani 0.5 2 d S TU P . .
C12 C 0.4348(5) 0.3424(5) 0.5614(4) 0.092(3) Uani 0.5 1 d . U P . .
H12 H 0.409259 0.304042 0.578452 0.110 Uiso 0.5 1 calc R U P . .
C13 C 0.3608(6) 0.4179(5) 0.4204(4) 0.096(3) Uani 0.5 1 d . U P . .
H13 H 0.319701 0.393887 0.405717 0.115 Uiso 0.5 1 calc R U P . .
C14 C 0.4735(4) 0.5265(4) 0.4219(5) 0.094(3) Uani 0.5 2 d S TU P . .
C15 C 0.4078(5) 0.4842(5) 0.4034(3) 0.084(2) Uani 0.5 1 d . U P . .
C16 C 0.3898(6) 0.5081(6) 0.3674(4) 0.078(3) Uani 0.5 1 d . U P . .
H16 H 0.353093 0.478018 0.350422 0.094 Uiso 0.5 1 calc R U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.452(10) . ?
C1 C6 1.498(4) . ?
C1 C2 1.499(4) . ?
C1 H1 0.9800 . ?
C1 H6 0.206(14) 9_556 ?
C2 C3 1.499(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 H5A 0.940(19) 9_556 ?
C3 C4 1.498(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 H4B 0.146(14) 9_556 ?
C4 C5 1.499(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.499(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N1 1.470(10) . ?
C6 H6 0.9800 . ?
In1 O2 2.0323(4) . ?
In1 O1 2.128(5) . ?
In1 O3 2.158(2) . ?
In1 O3 2.158(2) 11_656 ?
In1 O3 2.158(2) 19_655 ?
In1 O3 2.158(2) 16_557 ?
Cu1 O5 1.880(5) . ?
Cu1 N2 1.887(8) . ?
Cu1 O4 1.891(5) . ?
Cu1 N1 1.897(8) . ?
Cu1 Cu1 2.867(3) 21_665 ?
O3 C7 1.254(3) . ?
O4 C11 1.318(15) . ?
O5 C14 1.332(15) . ?
O6 N3 1.173(11) . ?
O7 N3 1.201(16) . ?
N1 C12 1.301(12) . ?
N2 C13 1.288(12) . ?
C7 C8 1.473(7) . ?
C8 C16 1.387(12) 9_556 ?
C8 C16 1.387(12) 13_666 ?
C8 C9 1.413(11) 21_665 ?
C8 C9 1.413(11) . ?
C9 C10 1.418(13) . ?
C9 H9 0.9300 . ?
C9 H16 1.226(17) 9_556 ?
C10 C11 1.385(11) . ?
C10 C12 1.470(13) . ?
C11 C14 1.009(19) 13_666 ?
C12 H12 0.9300 . ?
C12 H13 1.282(16) 9_556 ?
C13 C15 1.445(14) . ?
C13 H13 0.9300 . ?
C14 C15 1.433(11) 21_665 ?
C14 C15 1.433(11) . ?
C15 C16 1.366(14) . ?
C16 H16 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
N2 C1 C6 107.9(6) . . ?
N2 C1 C2 120.4(6) . . ?
C6 C1 C2 111.5 . . ?
N2 C1 H1 105.3 . . ?
C6 C1 H1 105.3 . . ?
C2 C1 H1 105.3 . . ?
N2 C1 H6 121.6(14) . 9_556 ?
C2 C1 H6 111.4(18) . 9_556 ?
H1 C1 H6 84.0 . 9_556 ?
C1 C2 C3 111.4 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2B 109.3 . . ?
C3 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C3 C2 H6 105.4(5) . 9_556 ?
H2A C2 H6 115.4 . 9_556 ?
H2B C2 H6 109.2 . 9_556 ?
C1 C2 H5A 123.29(16) . 9_556 ?
C3 C2 H5A 124.59(18) . 9_556 ?
H2A C2 H5A 61.8 . 9_556 ?
H2B C2 H5A 46.2 . 9_556 ?
H6 C2 H5A 128.5 9_556 9_556 ?
C4 C3 C2 111.5 . . ?
C4 C3 H3A 109.3 . . ?
C2 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H4A 85.5(9) . 9_556 ?
C2 C3 H4A 94.1(5) . 9_556 ?
H3B C3 H4A 144.1 . 9_556 ?
C2 C3 H4B 140(4) . 9_556 ?
H3A C3 H4B 99.1 . 9_556 ?
H3B C3 H4B 87.6 . 9_556 ?
H4A C3 H4B 91.9 9_556 9_556 ?
C3 C4 C5 111.5 . . ?
C3 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4B 112.5(4) . 9_556 ?
H4A C4 H4B 106.4 . 9_556 ?
H4B C4 H4B 111.2 . 9_556 ?
C6 C5 C4 111.5 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5B 109.3 . . ?
C4 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
N1 C6 C1 110.2(6) . . ?
N1 C6 C5 115.9(6) . . ?
C1 C6 C5 111.5 . . ?
N1 C6 H6 106.2 . . ?
C1 C6 H6 106.2 . . ?
C5 C6 H6 106.2 . . ?
N1 C6 H6 110.2(7) . 9_556 ?
C5 C6 H6 108.8(4) . 9_556 ?
H6 C6 H6 109.3 . 9_556 ?
O2 In1 O1 180.0 . . ?
O2 In1 O3 93.58(8) . . ?
O1 In1 O3 86.42(7) . . ?
O2 In1 O3 93.58(7) . 11_656 ?
O1 In1 O3 86.42(8) . 11_656 ?
O3 In1 O3 172.84(15) . 11_656 ?
O2 In1 O3 93.58(7) . 19_655 ?
O1 In1 O3 86.42(8) . 19_655 ?
O3 In1 O3 89.06(17) . 19_655 ?
O3 In1 O3 90.49(17) 11_656 19_655 ?
O2 In1 O3 93.58(8) . 16_557 ?
O1 In1 O3 86.42(7) . 16_557 ?
O3 In1 O3 90.49(17) . 16_557 ?
O3 In1 O3 89.06(17) 11_656 16_557 ?
O3 In1 O3 172.84(15) 19_655 16_557 ?
O5 Cu1 N2 94.9(3) . . ?
O5 Cu1 O4 81.0(3) . . ?
N2 Cu1 O4 169.6(5) . . ?
O5 Cu1 N1 173.5(5) . . ?
N2 Cu1 N1 88.2(3) . . ?
O4 Cu1 N1 95.0(3) . . ?
O5 Cu1 Cu1 40.30(19) . 21_665 ?
N2 Cu1 Cu1 134.4(2) . 21_665 ?
O4 Cu1 Cu1 40.68(19) . 21_665 ?
N1 Cu1 Cu1 135.4(3) . 21_665 ?
In1 O2 In1 120.000(2) 14_667 . ?
In1 O2 In1 120.0 14_667 3_655 ?
In1 O2 In1 120.000(2) . 3_655 ?
C7 O3 In1 133.8(3) . . ?
C11 O4 Cu1 130.1(3) . 21_665 ?
C11 O4 Cu1 130.1(3) . . ?
Cu1 O4 Cu1 98.6(4) 21_665 . ?
C11 O4 Cu1 111.9(8) . 9_556 ?
Cu1 O4 Cu1 98.1(4) 21_665 9_556 ?
C11 O4 Cu1 111.9(8) . 13_666 ?
Cu1 O4 Cu1 98.1(4) . 13_666 ?
Cu1 O4 Cu1 73.2(3) 9_556 13_666 ?
C14 O5 O4 76.5(10) . 13_666 ?
C14 O5 O4 76.5(10) . 9_556 ?
C14 O5 Cu1 128.2(4) . . ?
O4 O5 Cu1 87.7(5) 13_666 . ?
O4 O5 Cu1 87.7(5) 9_556 . ?
C14 O5 Cu1 128.2(4) . 21_665 ?
O4 O5 Cu1 87.7(5) 13_666 21_665 ?
O4 O5 Cu1 87.7(5) 9_556 21_665 ?
Cu1 O5 Cu1 99.4(4) . 21_665 ?
C12 N1 C6 125.0(8) . . ?
C12 N1 C1 109.3(8) . 9_556 ?
C12 N1 Cu1 124.1(7) . . ?
C6 N1 Cu1 109.6(5) . . ?
C1 N1 Cu1 111.9(5) 9_556 . ?
C12 N1 Cu1 112.7(8) . 9_556 ?
C6 N1 Cu1 98.0(5) . 9_556 ?
C1 N1 Cu1 81.4(4) 9_556 9_556 ?
N1 N2 C13 91.2(10) 9_556 . ?
N1 N2 C1 97.2(10) 9_556 . ?
C13 N2 C1 123.2(8) . . ?
N1 N2 C6 61.2(8) 9_556 9_556 ?
C13 N2 C6 122.8(9) . 9_556 ?
N1 N2 Cu1 97.7(8) 9_556 . ?
C13 N2 Cu1 125.0(7) . . ?
C1 N2 Cu1 109.3(5) . . ?
C6 N2 Cu1 108.6(5) 9_556 . ?
N1 N2 Cu1 55.3(6) 9_556 9_556 ?
C13 N2 Cu1 118.1(7) . 9_556 ?
C1 N2 Cu1 112.5(5) . 9_556 ?
C6 N2 Cu1 87.5(5) 9_556 9_556 ?
O6 N3 O6 123(2) . 19_655 ?
O6 N3 O7 118.2(11) . . ?
O6 N3 O7 118.2(11) 19_655 . ?
O3 C7 O3 126.6(5) 21_665 . ?
O3 C7 C8 116.7(2) 21_665 . ?
O3 C7 C8 116.7(2) . . ?
C16 C8 C16 114.5(10) 9_556 13_666 ?
C16 C8 C9 120.7(6) 9_556 21_665 ?
C16 C8 C9 120.7(6) 13_666 . ?
C9 C8 C9 113.8(10) 21_665 . ?
C16 C8 C7 119.5(5) 9_556 . ?
C16 C8 C7 119.5(5) 13_666 . ?
C9 C8 C7 119.8(5) 21_665 . ?
C9 C8 C7 119.8(5) . . ?
C8 C9 C10 122.8(8) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C8 C9 H16 98.8(10) . 9_556 ?
C10 C9 H16 120.1(11) . 9_556 ?
H9 C9 H16 47.0 . 9_556 ?
C11 C10 C9 118.0(9) . . ?
C11 C10 C12 126.5(9) . . ?
C9 C10 C12 115.4(9) . . ?
C14 C11 O4 101.4(15) 13_666 . ?
C14 C11 C10 86.2(11) 13_666 21_665 ?
O4 C11 C10 119.0(6) . 21_665 ?
C14 C11 C10 86.2(11) 13_666 . ?
O4 C11 C10 119.0(6) . . ?
C10 C11 C10 121.9(12) 21_665 . ?
O4 C11 O5 56.8(8) . 9_556 ?
C10 C11 O5 106.8(9) 21_665 9_556 ?
C10 C11 O5 106.9(9) . 9_556 ?
O4 C11 O5 56.8(8) . 13_666 ?
C10 C11 O5 106.8(9) 21_665 13_666 ?
C10 C11 O5 106.9(9) . 13_666 ?
N1 C12 C10 124.8(9) . . ?
N1 C12 H12 117.6 . . ?
C10 C12 H12 117.6 . . ?
N1 C12 H13 114.7(11) . 9_556 ?
C10 C12 H13 108.8(10) . 9_556 ?
N2 C13 C15 126.1(9) . . ?
N2 C13 H13 116.9 . . ?
C15 C13 H13 116.9 . . ?
C11 C14 O5 103.3(15) 13_666 . ?
C11 C14 O5 103.3(15) 9_556 . ?
C11 C14 C15 88.2(11) 13_666 21_665 ?
C11 C14 C15 88.2(11) 9_556 21_665 ?
O5 C14 C15 119.9(6) . 21_665 ?
C11 C14 C15 88.2(11) 13_666 . ?
C11 C14 C15 88.2(11) 9_556 . ?
O5 C14 C15 119.9(6) . . ?
C15 C14 C15 119.3(11) 21_665 . ?
C11 C14 C10 56.5(8) 13_666 13_666 ?
C11 C14 C10 56.5(8) 9_556 13_666 ?
O5 C14 C10 121.2(8) . 13_666 ?
C15 C14 C10 114.2(11) . 13_666 ?
C11 C14 C10 56.5(8) 13_666 9_556 ?
C11 C14 C10 56.5(8) 9_556 9_556 ?
O5 C14 C10 121.2(8) . 9_556 ?
C15 C14 C10 114.2(11) 21_665 9_556 ?
C10 C14 C10 93.8(11) 13_666 9_556 ?
C11 C14 O4 45.5(10) 13_666 9_556 ?
C11 C14 O4 45.5(10) 9_556 9_556 ?
O5 C14 O4 57.8(8) . 9_556 ?
C15 C14 O4 109.7(9) 21_665 9_556 ?
C15 C14 O4 109.7(9) . 9_556 ?
C10 C14 O4 84.2(9) 13_666 9_556 ?
C10 C14 O4 84.2(9) 9_556 9_556 ?
C11 C14 O4 45.5(10) 13_666 13_666 ?
C11 C14 O4 45.5(10) 9_556 13_666 ?
O5 C14 O4 57.8(8) . 13_666 ?
C15 C14 O4 109.7(9) 21_665 13_666 ?
C15 C14 O4 109.7(9) . 13_666 ?
C10 C14 O4 84.2(9) 13_666 13_666 ?
C10 C14 O4 84.2(9) 9_556 13_666 ?
C10 C15 C16 92.5(12) 9_556 . ?
C10 C15 C14 88.5(13) 9_556 . ?
C16 C15 C14 117.4(9) . . ?
C10 C15 C13 90.0(12) 9_556 . ?
C16 C15 C13 119.2(9) . . ?
C14 C15 C13 123.4(8) . . ?
C10 C15 C9 67.7(10) 9_556 9_556 ?
C14 C15 C9 115.9(9) . 9_556 ?
C13 C15 C9 115.5(9) . 9_556 ?
C10 C15 C12 58.9(10) 9_556 9_556 ?
C16 C15 C12 114.6(9) . 9_556 ?
C14 C15 C12 118.7(9) . 9_556 ?
C9 C15 C12 98.6(8) 9_556 9_556 ?
C10 C15 C11 52.8(10) 9_556 13_666 ?
C16 C15 C11 111.8(9) . 13_666 ?
C13 C15 C11 117.3(8) . 13_666 ?
C9 C15 C11 96.1(9) 9_556 13_666 ?
C12 C15 C11 95.6(8) 9_556 13_666 ?
C10 C15 C11 52.8(10) 9_556 9_556 ?
C16 C15 C11 111.8(9) . 9_556 ?
C13 C15 C11 117.3(8) . 9_556 ?
C9 C15 C11 96.1(9) 9_556 9_556 ?
C12 C15 C11 95.6(8) 9_556 9_556 ?
C15 C16 C8 122.6(10) . 13_666 ?
C15 C16 H16 118.7 . . ?
C8 C16 H16 118.7 13_666 . ?

_refine_diff_density_max         1.002
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.076



