# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1547301'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_2                   
;
PROBLEM: Check Calcd Residual Density  0.69A From      I2      -3.76 eA-3
RESPONSE: After careful investigation, there is no possible atom at this site. The residual density is very close to the heavy atom. All atoms is refined anisotropically.
;
_vrf_PLAT971_2                   
;
PROBLEM: Check Calcd Residual Density  0.82A From      I2       3.41 eA-3
RESPONSE: After careful investigation, there is no possible atom at this site. The residual density is very close to the heavy atom. All atoms is refined anisotropically.
;
# Added during the CSD deposition process: Tuesday 02 May 2017 05:34 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C71 H51 Cu4 I4 N7 O6'
_chemical_formula_weight         1859.95

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_H-M_alt        'P 63'
_space_group_name_Hall           'P 6c'

_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'

_cell_length_a                   15.7192(13)
_cell_length_b                   15.7192(13)
_cell_length_c                   15.4669(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     3309.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    62174
_cell_measurement_theta_min      2.10
_cell_measurement_theta_max      30.10

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_F_000             1804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.571
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.099
_exptl_absorpt_coefficient_mu    3.192
_shelx_estimated_absorpt_T_min   0.263
_shelx_estimated_absorpt_T_max   0.743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_T_max  0.6273
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56597
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.496
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6427
_reflns_number_gt                5146
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.933
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    X-SEED
_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)+(0.0118P)²+34.2677P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2078 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.016(12)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6427
_refine_ls_number_parameters     286
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0808
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1165
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
I1 I 0.51605(4) 0.15740(4) 0.97827(6) 0.02904(15) Uani 1 1 d . . . . .
I2 I 0.6667 0.3333 0.74264(9) 0.0536(5) Uani 1 3 d S T P . .
Cu2 Cu 0.6667 0.3333 1.02116(14) 0.0227(4) Uani 1 3 d S T P . .
Cu1 Cu 0.55949(10) 0.31409(10) 0.88214(11) 0.0348(3) Uani 1 1 d . . . . .
O1 O 0.1796(6) 0.2016(7) 0.5851(6) 0.0320(19) Uani 1 1 d . . . . .
O2 O 0.2303(7) 0.4640(6) 0.7515(7) 0.045(2) Uani 1 1 d . . . . .
N2 N 0.2280(7) 0.3348(7) 0.6780(6) 0.0274(19) Uani 1 1 d . . . . .
N3 N 0.6667 0.3333 1.1472(10) 0.026(3) Uani 1 3 d S T P . .
C3 C 0.3000(9) 0.3260(9) 0.7271(7) 0.030(2) Uani 1 1 d . . . . .
C9 C 0.1724(8) 0.2701(8) 0.6110(7) 0.026(2) Uani 1 1 d . . . . .
C23 C -0.0724(8) 0.2546(9) 0.5657(8) 0.030(2) Uani 1 1 d . . . . .
N1 N 0.4424(8) 0.3080(8) 0.8203(7) 0.039(2) Uani 1 1 d . . . . .
C11 C -0.0017(9) 0.2836(9) 0.7354(7) 0.032(3) Uani 1 1 d . . . . .
C17 C -0.0065(8) 0.2155(9) 0.5953(7) 0.029(2) Uani 1 1 d . . . . .
H17 H -0.0216 0.1536 0.5644 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1202(8) 0.3891(8) 0.6290(7) 0.025(2) Uani 1 1 d D . . . .
C18 C -0.0526(9) 0.3404(10) 0.6092(8) 0.034(3) Uani 1 1 d . . . . .
C6 C 0.1992(8) 0.4044(8) 0.6949(7) 0.031(2) Uani 1 1 d . . . . .
C16 C -0.0181(9) 0.2010(9) 0.6907(8) 0.032(2) Uani 1 1 d . . . . .
C8 C 0.1007(7) 0.2993(8) 0.5785(7) 0.0232(19) Uani 1 1 d . . . . .
C10 C 0.0261(9) 0.3716(9) 0.6772(8) 0.035(3) Uani 1 1 d D . . . .
H10 H 0.0364 0.4308 0.7101 0.042 Uiso 1 1 calc R U . . .
C22 C -0.1450(8) 0.2127(10) 0.5033(8) 0.038(3) Uani 1 1 d . . . . .
H22 H -0.1570 0.1547 0.4737 0.046 Uiso 1 1 calc R U . . .
C21 C -0.2002(8) 0.2581(10) 0.4851(11) 0.045(3) Uani 1 1 d . . . . .
H21 H -0.2512 0.2303 0.4432 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3183(10) 0.3531(11) 0.8099(8) 0.044(3) Uani 1 1 d . . . . .
H2 H 0.2815 0.3775 0.8387 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3511(10) 0.2827(10) 0.6888(9) 0.040(3) Uani 1 1 d . . . . .
H4 H 0.3374 0.2586 0.6312 0.048 Uiso 1 1 calc R U . . .
C13 C -0.0314(11) 0.1940(14) 0.8668(9) 0.061(5) Uani 1 1 d . . . . .
H13 H -0.0342 0.1917 0.9282 0.073 Uiso 1 1 calc R U . . .
C12 C -0.0084(10) 0.2800(12) 0.8251(9) 0.046(3) Uani 1 1 d . . . . .
H12 H 0.0029 0.3363 0.8571 0.055 Uiso 1 1 calc R U . . .
C25 C 0.6667 0.3333 1.3164(12) 0.034(4) Uani 1 3 d S T P . .
H25A H 0.6240 0.2663 1.3376 0.050 Uiso 0.3333 1 calc R U P . .
H25B H 0.6423 0.3760 1.3376 0.050 Uiso 0.3333 1 calc R U P . .
H25C H 0.7337 0.3577 1.3376 0.050 Uiso 0.3333 1 calc R U P . .
C1 C 0.3921(11) 0.3453(10) 0.8544(8) 0.042(3) Uani 1 1 d . . . . .
H1 H 0.4063 0.3683 0.9123 0.051 Uiso 1 1 calc R U . . .
C5 C 0.4214(10) 0.2766(10) 0.7378(9) 0.045(3) Uani 1 1 d . . . . .
H5 H 0.4568 0.2488 0.7119 0.054 Uiso 1 1 calc R U . . .
C19 C -0.1073(10) 0.3851(11) 0.5892(9) 0.042(3) Uani 1 1 d . . . . .
H19 H -0.0946 0.4440 0.6175 0.050 Uiso 1 1 calc R U . . .
C15 C -0.0425(9) 0.1127(10) 0.7344(9) 0.043(3) Uani 1 1 d . . . . .
H15 H -0.0529 0.0561 0.7033 0.052 Uiso 1 1 calc R U . . .
C20 C -0.1812(10) 0.3420(12) 0.5271(10) 0.052(4) Uani 1 1 d . . . . .
H20 H -0.2192 0.3719 0.5137 0.063 Uiso 1 1 calc R U . . .
C14 C -0.0506(11) 0.1107(12) 0.8211(10) 0.055(4) Uani 1 1 d . . . . .
H14 H -0.0699 0.0512 0.8513 0.065 Uiso 1 1 calc R U . . .
C24 C 0.6667 0.3333 1.2212(12) 0.016(3) Uani 1 3 d S T P . .
H7 H 0.134(4) 0.447(4) 0.598(5) 0.01(2) Uiso 1 1 d D . . . .
H8 H 0.096(7) 0.300(7) 0.522(6) 0.00(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.6575(15) . ?
I1 Cu2 2.6733(8) . ?
I1 Cu1 2.7496(17) 3_655 ?
I2 Cu1 2.660(2) 3_655 ?
I2 Cu1 2.660(2) 5_665 ?
I2 Cu1 2.660(2) . ?
Cu2 N3 1.949(16) . ?
Cu2 Cu1 2.654(2) 3_655 ?
Cu2 Cu1 2.654(2) 5_665 ?
Cu2 Cu1 2.654(2) . ?
Cu2 I1 2.6732(8) 3_655 ?
Cu2 I1 2.6732(8) 5_665 ?
Cu1 N1 2.033(11) . ?
Cu1 Cu1 2.695(2) 5_665 ?
Cu1 Cu1 2.695(2) 3_655 ?
Cu1 I1 2.7495(17) 5_665 ?
O1 C9 1.206(14) . ?
O2 C6 1.194(14) . ?
N2 C6 1.403(14) . ?
N2 C9 1.408(15) . ?
N2 C3 1.427(13) . ?
N3 C24 1.14(2) . ?
C3 C2 1.335(17) . ?
C3 C4 1.416(17) . ?
C9 C8 1.500(14) . ?
C23 C22 1.385(16) . ?
C23 C18 1.395(18) . ?
C23 C17 1.515(15) . ?
N1 C1 1.308(17) . ?
N1 C5 1.347(16) . ?
C11 C16 1.376(17) . ?
C11 C12 1.390(17) . ?
C11 C10 1.521(17) . ?
C17 C16 1.491(16) . ?
C17 C8 1.557(15) . ?
C17 H17 1.0000 . ?
C7 C8 1.504(15) . ?
C7 C6 1.528(15) . ?
C7 C10 1.554(16) . ?
C7 H7 0.959(14) . ?
C18 C19 1.391(17) . ?
C18 C10 1.507(17) . ?
C16 C15 1.414(17) . ?
C8 H8 0.88(10) . ?
C10 H10 1.0000 . ?
C22 C21 1.402(16) . ?
C22 H22 0.9500 . ?
C21 C20 1.36(2) . ?
C21 H21 0.9500 . ?
C2 C1 1.406(19) . ?
C2 H2 0.9500 . ?
C4 C5 1.383(18) . ?
C4 H4 0.9500 . ?
C13 C12 1.37(2) . ?
C13 C14 1.38(2) . ?
C13 H13 0.9500 . ?
C12 H12 0.9500 . ?
C25 C24 1.47(3) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C1 H1 0.9500 . ?
C5 H5 0.9500 . ?
C19 C20 1.39(2) . ?
C19 H19 0.9500 . ?
C15 C14 1.35(2) . ?
C15 H15 0.9500 . ?
C20 H20 0.9500 . ?
C14 H14 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cu1 I1 Cu2 59.72(5) . . ?
Cu1 I1 Cu1 59.76(6) . 3_655 ?
Cu2 I1 Cu1 58.59(5) . 3_655 ?
Cu1 I2 Cu1 60.86(6) 3_655 5_665 ?
Cu1 I2 Cu1 60.86(6) 3_655 . ?
Cu1 I2 Cu1 60.86(6) 5_665 . ?
N3 Cu2 Cu1 144.11(4) . 3_655 ?
N3 Cu2 Cu1 144.11(4) . 5_665 ?
Cu1 Cu2 Cu1 61.01(7) 3_655 5_665 ?
N3 Cu2 Cu1 144.11(4) . . ?
Cu1 Cu2 Cu1 61.02(7) 3_655 . ?
Cu1 Cu2 Cu1 61.02(7) 5_665 . ?
N3 Cu2 I1 104.37(5) . 3_655 ?
Cu1 Cu2 I1 59.84(4) 3_655 3_655 ?
Cu1 Cu2 I1 62.14(5) 5_665 3_655 ?
Cu1 Cu2 I1 111.50(8) . 3_655 ?
N3 Cu2 I1 104.37(5) . . ?
Cu1 Cu2 I1 62.14(5) 3_655 . ?
Cu1 Cu2 I1 111.50(8) 5_665 . ?
Cu1 Cu2 I1 59.85(4) . . ?
I1 Cu2 I1 114.06(4) 3_655 . ?
N3 Cu2 I1 104.37(5) . 5_665 ?
Cu1 Cu2 I1 111.50(8) 3_655 5_665 ?
Cu1 Cu2 I1 59.85(4) 5_665 5_665 ?
Cu1 Cu2 I1 62.14(5) . 5_665 ?
I1 Cu2 I1 114.06(4) 3_655 5_665 ?
I1 Cu2 I1 114.06(4) . 5_665 ?
N1 Cu1 Cu2 153.5(3) . . ?
N1 Cu1 I1 114.4(3) . . ?
Cu2 Cu1 I1 60.44(4) . . ?
N1 Cu1 I2 97.5(3) . . ?
Cu2 Cu1 I2 108.32(6) . . ?
I1 Cu1 I2 114.45(6) . . ?
N1 Cu1 Cu1 134.8(3) . 5_665 ?
Cu2 Cu1 Cu1 59.49(4) . 5_665 ?
I1 Cu1 Cu1 110.72(5) . 5_665 ?
I2 Cu1 Cu1 59.57(3) . 5_665 ?
N1 Cu1 Cu1 144.3(3) . 3_655 ?
Cu2 Cu1 Cu1 59.49(4) . 3_655 ?
I1 Cu1 Cu1 61.82(6) . 3_655 ?
I2 Cu1 Cu1 59.57(3) . 3_655 ?
Cu1 Cu1 Cu1 60.0 5_665 3_655 ?
N1 Cu1 I1 105.9(3) . 5_665 ?
Cu2 Cu1 I1 59.27(4) . 5_665 ?
I1 Cu1 I1 112.09(6) . 5_665 ?
I2 Cu1 I1 111.47(5) . 5_665 ?
Cu1 Cu1 I1 58.43(5) 5_665 5_665 ?
Cu1 Cu1 I1 107.96(5) 3_655 5_665 ?
C6 N2 C9 112.0(9) . . ?
C6 N2 C3 123.9(10) . . ?
C9 N2 C3 123.9(9) . . ?
C24 N3 Cu2 180.0 . . ?
C2 C3 C4 118.1(11) . . ?
C2 C3 N2 122.4(11) . . ?
C4 C3 N2 119.5(10) . . ?
O1 C9 N2 126.0(10) . . ?
O1 C9 C8 125.7(11) . . ?
N2 C9 C8 108.3(9) . . ?
C22 C23 C18 121.9(11) . . ?
C22 C23 C17 125.8(11) . . ?
C18 C23 C17 112.3(10) . . ?
C1 N1 C5 117.0(11) . . ?
C1 N1 Cu1 121.6(9) . . ?
C5 N1 Cu1 120.9(9) . . ?
C16 C11 C12 119.2(12) . . ?
C16 C11 C10 113.2(10) . . ?
C12 C11 C10 127.6(12) . . ?
C16 C17 C23 107.8(9) . . ?
C16 C17 C8 107.0(9) . . ?
C23 C17 C8 106.1(9) . . ?
C16 C17 H17 111.9 . . ?
C23 C17 H17 111.9 . . ?
C8 C17 H17 111.9 . . ?
C8 C7 C6 105.2(9) . . ?
C8 C7 C10 110.7(9) . . ?
C6 C7 C10 109.6(9) . . ?
C8 C7 H7 119(5) . . ?
C6 C7 H7 114(6) . . ?
C10 C7 H7 98.9(16) . . ?
C19 C18 C23 119.1(12) . . ?
C19 C18 C10 127.2(12) . . ?
C23 C18 C10 113.7(10) . . ?
O2 C6 N2 125.7(11) . . ?
O2 C6 C7 126.5(11) . . ?
N2 C6 C7 107.8(9) . . ?
C11 C16 C15 121.1(12) . . ?
C11 C16 C17 113.7(10) . . ?
C15 C16 C17 125.1(12) . . ?
C9 C8 C7 106.4(9) . . ?
C9 C8 C17 110.2(9) . . ?
C7 C8 C17 109.5(9) . . ?
C9 C8 H8 114(6) . . ?
C7 C8 H8 119(6) . . ?
C17 C8 H8 97(6) . . ?
C18 C10 C11 107.5(10) . . ?
C18 C10 C7 106.1(10) . . ?
C11 C10 C7 105.0(9) . . ?
C18 C10 H10 112.6 . . ?
C11 C10 H10 112.6 . . ?
C7 C10 H10 112.6 . . ?
C23 C22 C21 118.1(12) . . ?
C23 C22 H22 121.0 . . ?
C21 C22 H22 121.0 . . ?
C20 C21 C22 120.4(13) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C3 C2 C1 119.8(12) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C5 C4 C3 118.0(12) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
C12 C13 C14 121.2(13) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C13 C12 C11 119.1(14) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N1 C1 C2 123.5(12) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
N1 C5 C4 123.5(12) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C18 C19 C20 118.8(13) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C14 C15 C16 118.3(14) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C21 C20 C19 121.7(12) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
C15 C14 C13 121.0(14) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N3 C24 C25 180.000(17) . . ?

_refine_diff_density_max         3.872
_refine_diff_density_min         -4.426
_refine_diff_density_rms         0.168

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1547299'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H16 N2 O2'
_chemical_formula_weight         352.38

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

_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                   17.5818(6)
_cell_length_b                   12.0417(4)
_cell_length_c                   8.0384(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.0130(10)
_cell_angle_gamma                90
_cell_volume                     1680.83(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    53146
_cell_measurement_theta_min      2.05
_cell_measurement_theta_max      30.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.780
_shelx_estimated_absorpt_T_max   0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_T_max  0.6273
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            48213
_diffrn_reflns_av_unetI/netI     0.0207
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.173
_diffrn_reflns_theta_max         32.759
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6195
_reflns_number_gt                5207
_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       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    X-SEED
_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)+(0.0748P)²+0.5240P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6195
_refine_ls_number_parameters     308
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0550
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1182
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
O1 O 0.27340(4) 0.74136(6) 0.05761(9) 0.01920(15) Uani 1 1 d . . . . .
N2 N 0.19117(4) 0.85532(6) 0.17667(10) 0.01330(14) Uani 1 1 d . . . . .
O2 O 0.14052(4) 0.99023(6) 0.33231(9) 0.01713(14) Uani 1 1 d . . . . .
C10 C 0.36660(5) 0.95971(7) 0.11767(10) 0.01217(15) Uani 1 1 d . . . . .
C11 C 0.29221(5) 1.09763(7) 0.28278(10) 0.01187(15) Uani 1 1 d . . . . .
C6 C 0.26314(5) 0.81852(7) 0.14845(11) 0.01334(16) Uani 1 1 d . . . . .
C17 C 0.41853(5) 1.04146(7) 0.22489(11) 0.01302(15) Uani 1 1 d . . . . .
C23 C 0.30427(5) 1.02372(7) 0.00583(10) 0.01216(15) Uani 1 1 d . . . . .
C7 C 0.32406(5) 0.89368(7) 0.24384(11) 0.01212(15) Uani 1 1 d . . . . .
C8 C 0.27946(5) 0.97548(7) 0.33988(10) 0.01189(15) Uani 1 1 d . . . . .
C19 C 0.20032(5) 1.15483(7) 0.01335(11) 0.01390(16) Uani 1 1 d . . . . .
C18 C 0.26427(5) 1.09805(7) 0.09474(10) 0.01186(15) Uani 1 1 d . . . . .
C3 C 0.11987(5) 0.81197(8) 0.09269(12) 0.01530(16) Uani 1 1 d . . . . .
C14 C 0.49723(6) 1.20026(8) 0.43566(12) 0.01866(18) Uani 1 1 d . . . . .
C22 C 0.28050(5) 1.00695(8) -0.16586(11) 0.01574(17) Uani 1 1 d . . . . .
C12 C 0.37810(5) 1.11565(7) 0.31319(11) 0.01297(15) Uani 1 1 d . . . . .
C16 C 0.49827(5) 1.04600(8) 0.24324(12) 0.01587(17) Uani 1 1 d . . . . .
C20 C 0.17654(5) 1.13781(8) -0.15886(12) 0.01633(17) Uani 1 1 d . . . . .
C21 C 0.21670(6) 1.06494(8) -0.24795(11) 0.01753(17) Uani 1 1 d . . . . .
C9 C 0.19557(5) 0.94484(7) 0.28958(10) 0.01267(15) Uani 1 1 d . . . . .
C13 C 0.41720(6) 1.19521(8) 0.41911(12) 0.01634(17) Uani 1 1 d . . . . .
C15 C 0.53749(6) 1.12657(9) 0.34854(12) 0.01861(18) Uani 1 1 d . . . . .
C4 C 0.06740(6) 0.88245(9) -0.00112(14) 0.0230(2) Uani 1 1 d . . . . .
C2 C 0.10299(6) 0.70068(9) 0.10269(16) 0.0244(2) Uani 1 1 d . . . . .
N1 N -0.02024(6) 0.73037(10) -0.07019(15) 0.0327(2) Uani 1 1 d . . . . .
C5 C -0.00156(7) 0.83736(11) -0.07973(16) 0.0293(2) Uani 1 1 d . . . . .
C1 C 0.03210(7) 0.66493(11) 0.0179(2) 0.0344(3) Uani 1 1 d . . . . .
H1 H 0.1708(8) 1.2036(11) 0.0747(17) 0.015(3) Uiso 1 1 d . . . . .
H2 H 0.2934(8) 0.9683(12) 0.4634(17) 0.018(3) Uiso 1 1 d . . . . .
H3 H 0.2641(8) 1.1496(11) 0.3427(17) 0.015(3) Uiso 1 1 d . . . . .
H4 H 0.3615(8) 0.8468(12) 0.3180(19) 0.021(3) Uiso 1 1 d . . . . .
H5 H 0.3887(8) 1.2467(12) 0.4780(19) 0.020(3) Uiso 1 1 d . . . . .
H6 H 0.5263(8) 1.2575(12) 0.5122(18) 0.020(3) Uiso 1 1 d . . . . .
H7 H 0.5267(8) 0.9929(12) 0.1813(19) 0.023(3) Uiso 1 1 d . . . . .
H8 H 0.5941(9) 1.1326(13) 0.3627(19) 0.027(4) Uiso 1 1 d . . . . .
H9 H 0.3959(8) 0.9081(13) 0.0542(18) 0.022(3) Uiso 1 1 d . . . . .
H10 H 0.1307(9) 1.1776(13) -0.215(2) 0.028(4) Uiso 1 1 d . . . . .
H11 H 0.0794(9) 0.9626(14) -0.012(2) 0.034(4) Uiso 1 1 d . . . . .
H12 H 0.1390(10) 0.6505(15) 0.169(2) 0.039(5) Uiso 1 1 d . . . . .
H13 H 0.1986(9) 1.0541(14) -0.370(2) 0.030(4) Uiso 1 1 d . . . . .
H14 H 0.3081(9) 0.9549(13) -0.2289(19) 0.026(4) Uiso 1 1 d . . . . .
H15 H -0.0417(11) 0.8839(15) -0.148(2) 0.041(5) Uiso 1 1 d . . . . .
H16 H 0.0186(11) 0.5861(17) 0.032(2) 0.047(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.2126(11) . ?
N2 C6 1.3925(12) . ?
N2 C9 1.4035(11) . ?
N2 C3 1.4264(11) . ?
O2 C9 1.2073(11) . ?
C10 C23 1.5148(12) . ?
C10 C17 1.5163(12) . ?
C10 C7 1.5677(12) . ?
C10 H9 0.997(15) . ?
C11 C12 1.5072(12) . ?
C11 C18 1.5144(12) . ?
C11 C8 1.5674(12) . ?
C11 H3 0.971(14) . ?
C6 C7 1.5156(12) . ?
C17 C16 1.3877(12) . ?
C17 C12 1.4018(12) . ?
C23 C22 1.3926(12) . ?
C23 C18 1.4014(12) . ?
C7 C8 1.5397(12) . ?
C7 H4 0.993(15) . ?
C8 C9 1.5128(12) . ?
C8 H2 0.989(14) . ?
C19 C18 1.3891(12) . ?
C19 C20 1.3971(13) . ?
C19 H1 0.968(14) . ?
C3 C2 1.3777(14) . ?
C3 C4 1.3863(14) . ?
C14 C15 1.3907(15) . ?
C14 C13 1.3939(13) . ?
C14 H6 1.008(15) . ?
C22 C21 1.3963(13) . ?
C22 H14 0.981(16) . ?
C12 C13 1.3899(12) . ?
C16 C15 1.3966(13) . ?
C16 H7 0.992(15) . ?
C20 C21 1.3927(14) . ?
C20 H10 0.985(16) . ?
C21 H13 0.990(16) . ?
C13 H5 0.966(15) . ?
C15 H8 0.986(16) . ?
C4 C5 1.3872(15) . ?
C4 H11 0.995(17) . ?
C2 C1 1.3918(16) . ?
C2 H12 0.971(18) . ?
N1 C1 1.3287(18) . ?
N1 C5 1.3347(18) . ?
C5 H15 0.998(18) . ?
C1 H16 0.99(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
C6 N2 C9 112.98(7) . . ?
C6 N2 C3 124.06(8) . . ?
C9 N2 C3 122.85(8) . . ?
C23 C10 C17 108.79(7) . . ?
C23 C10 C7 105.54(7) . . ?
C17 C10 C7 105.51(7) . . ?
C23 C10 H9 113.4(8) . . ?
C17 C10 H9 112.5(9) . . ?
C7 C10 H9 110.6(9) . . ?
C12 C11 C18 108.75(7) . . ?
C12 C11 C8 105.85(7) . . ?
C18 C11 C8 104.86(7) . . ?
C12 C11 H3 113.7(8) . . ?
C18 C11 H3 112.5(8) . . ?
C8 C11 H3 110.6(8) . . ?
O1 C6 N2 124.52(8) . . ?
O1 C6 C7 127.03(8) . . ?
N2 C6 C7 108.40(7) . . ?
C16 C17 C12 120.34(8) . . ?
C16 C17 C10 126.47(8) . . ?
C12 C17 C10 113.18(7) . . ?
C22 C23 C18 120.09(8) . . ?
C22 C23 C10 126.24(8) . . ?
C18 C23 C10 113.36(7) . . ?
C6 C7 C8 105.11(7) . . ?
C6 C7 C10 110.28(7) . . ?
C8 C7 C10 109.39(7) . . ?
C6 C7 H4 108.3(8) . . ?
C8 C7 H4 113.9(9) . . ?
C10 C7 H4 109.8(9) . . ?
C9 C8 C7 105.18(7) . . ?
C9 C8 C11 109.19(7) . . ?
C7 C8 C11 110.25(7) . . ?
C9 C8 H2 109.0(8) . . ?
C7 C8 H2 112.4(8) . . ?
C11 C8 H2 110.6(8) . . ?
C18 C19 C20 119.27(8) . . ?
C18 C19 H1 121.1(8) . . ?
C20 C19 H1 119.6(8) . . ?
C19 C18 C23 120.54(8) . . ?
C19 C18 C11 125.71(8) . . ?
C23 C18 C11 113.37(7) . . ?
C2 C3 C4 119.75(9) . . ?
C2 C3 N2 120.64(9) . . ?
C4 C3 N2 119.60(9) . . ?
C15 C14 C13 120.66(9) . . ?
C15 C14 H6 119.6(9) . . ?
C13 C14 H6 119.7(8) . . ?
C23 C22 C21 119.34(8) . . ?
C23 C22 H14 120.6(9) . . ?
C21 C22 H14 120.1(9) . . ?
C13 C12 C17 120.54(8) . . ?
C13 C12 C11 125.83(8) . . ?
C17 C12 C11 113.62(7) . . ?
C17 C16 C15 119.11(9) . . ?
C17 C16 H7 120.1(8) . . ?
C15 C16 H7 120.8(8) . . ?
C21 C20 C19 120.32(8) . . ?
C21 C20 H10 120.9(9) . . ?
C19 C20 H10 118.7(9) . . ?
C20 C21 C22 120.43(8) . . ?
C20 C21 H13 118.8(9) . . ?
C22 C21 H13 120.8(9) . . ?
O2 C9 N2 124.49(8) . . ?
O2 C9 C8 127.24(8) . . ?
N2 C9 C8 108.23(7) . . ?
C12 C13 C14 118.92(9) . . ?
C12 C13 H5 119.9(9) . . ?
C14 C13 H5 121.2(9) . . ?
C14 C15 C16 120.44(9) . . ?
C14 C15 H8 118.6(9) . . ?
C16 C15 H8 121.0(9) . . ?
C3 C4 C5 117.89(10) . . ?
C3 C4 H11 120.7(9) . . ?
C5 C4 H11 121.4(9) . . ?
C3 C2 C1 117.18(11) . . ?
C3 C2 H12 120.6(11) . . ?
C1 C2 H12 122.2(11) . . ?
C1 N1 C5 116.55(10) . . ?
N1 C5 C4 123.85(11) . . ?
N1 C5 H15 114.5(11) . . ?
C4 C5 H15 121.6(11) . . ?
N1 C1 C2 124.74(11) . . ?
N1 C1 H16 118.1(11) . . ?
C2 C1 H16 117.0(11) . . ?

_refine_diff_density_max         0.561
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.061

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1547300'
_audit_update_record             
;
2017-05-02 deposited with the CCDC.
2017-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H38 Cu2 I2 N6 O4'
_chemical_formula_weight         1167.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   16.5376(18)
_cell_length_b                   7.7350(7)
_cell_length_c                   34.802(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.830(3)
_cell_angle_gamma                90
_cell_volume                     4410.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    101249
_cell_measurement_theta_min      1.85
_cell_measurement_theta_max      30.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.759
_exptl_crystal_F_000             2304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.523
_exptl_crystal_size_mid          0.198
_exptl_crystal_size_min          0.074
_exptl_absorpt_coefficient_mu    2.419
_shelx_estimated_absorpt_T_min   0.364
_shelx_estimated_absorpt_T_max   0.841
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4261
_exptl_absorpt_correction_T_max  0.6273
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Apex CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            93202
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_theta_min         2.363
_diffrn_reflns_theta_max         32.915
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             8184
_reflns_number_gt                7488
_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       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    X-SEED
_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)+(0.0208P)²+56.2350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014)'
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8184
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0534
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1092
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_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
I1 I 0.07967(2) 0.65751(3) 0.04668(2) 0.01480(6) Uani 1 1 d . . . . .
Cu1 Cu 0.02190(3) 0.36047(5) 0.02061(2) 0.01391(9) Uani 1 1 d . . . . .
N1 N -0.04377(19) 0.2477(4) 0.06008(8) 0.0140(5) Uani 1 1 d . . . . .
C5 C -0.0397(2) 0.0754(4) 0.06533(10) 0.0144(6) Uani 1 1 d . . . . .
H5 H 0.0039 0.0150 0.0562 0.017 Uiso 1 1 calc R U . . .
C3 C -0.1598(2) 0.0668(4) 0.09627(9) 0.0119(5) Uani 1 1 d . . . . .
C16 C -0.2458(2) -0.3516(4) 0.17942(9) 0.0130(5) Uani 1 1 d . . . . .
N2 N -0.22312(17) -0.0252(4) 0.11141(8) 0.0118(5) Uani 1 1 d . . . . .
C1 C -0.1050(2) 0.3301(4) 0.07439(10) 0.0152(6) Uani 1 1 d . . . . .
H1 H -0.1075 0.4525 0.0723 0.018 Uiso 1 1 calc R U . . .
C2 C -0.1644(2) 0.2467(4) 0.09197(10) 0.0148(6) Uani 1 1 d . . . . .
H2 H -0.2074 0.3101 0.1009 0.018 Uiso 1 1 calc R U . . .
C4 C -0.0949(2) -0.0194(4) 0.08322(9) 0.0134(6) Uani 1 1 d . . . . .
H4 H -0.0886 -0.1408 0.0865 0.016 Uiso 1 1 calc R U . . .
C12 C -0.2138(2) -0.1443(5) 0.23183(10) 0.0179(6) Uani 1 1 d . . . . .
H12 H -0.2275 -0.0448 0.2456 0.021 Uiso 1 1 calc R U . . .
C23 C -0.3906(2) -0.4170(5) 0.16223(9) 0.0143(6) Uani 1 1 d . . . . .
N3 N 0.11323(19) 0.1997(4) 0.01395(9) 0.0163(5) Uani 1 1 d . . . . .
C17 C -0.3103(2) -0.3991(4) 0.14591(9) 0.0120(5) Uani 1 1 d . . . . .
H17 H -0.2959 -0.5062 0.1322 0.014 Uiso 1 1 calc R U . . .
C10 C -0.3477(2) -0.1270(4) 0.18408(9) 0.0142(6) Uani 1 1 d . . . . .
H10 H -0.3621 -0.0254 0.1996 0.017 Uiso 1 1 calc R U . . .
C11 C -0.2662(2) -0.2051(4) 0.20006(9) 0.0132(6) Uani 1 1 d . . . . .
C15 C -0.1727(2) -0.4374(5) 0.19075(10) 0.0162(6) Uani 1 1 d . . . . .
H15 H -0.1583 -0.5361 0.1769 0.019 Uiso 1 1 calc R U . . .
C18 C -0.4105(2) -0.2700(5) 0.18242(10) 0.0159(6) Uani 1 1 d . . . . .
C24 C 0.1639(2) 0.1053(4) 0.00969(10) 0.0154(6) Uani 1 1 d . . . . .
C19 C -0.4832(2) -0.2654(6) 0.19834(11) 0.0217(7) Uani 1 1 d . . . . .
H19 H -0.4974 -0.1654 0.2118 0.026 Uiso 1 1 calc R U . . .
C14 C -0.1206(2) -0.3761(5) 0.22294(11) 0.0197(7) Uani 1 1 d . . . . .
H14 H -0.0706 -0.4344 0.2310 0.024 Uiso 1 1 calc R U . . .
C21 C -0.5148(2) -0.5534(6) 0.17461(11) 0.0228(8) Uani 1 1 d . . . . .
H21 H -0.5504 -0.6503 0.1722 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2287(2) -0.0161(5) 0.00421(11) 0.0195(7) Uani 1 1 d . . . . .
H25A H 0.2603 0.0290 -0.0155 0.029 Uiso 1 1 calc R U . . .
H25B H 0.2046 -0.1277 -0.0044 0.029 Uiso 1 1 calc R U . . .
H25C H 0.2647 -0.0313 0.0288 0.029 Uiso 1 1 calc R U . . .
C13 C -0.1406(2) -0.2320(5) 0.24322(11) 0.0210(7) Uani 1 1 d . . . . .
H13 H -0.1045 -0.1925 0.2650 0.025 Uiso 1 1 calc R U . . .
C22 C -0.4422(2) -0.5588(5) 0.15813(10) 0.0190(7) Uani 1 1 d . . . . .
H22 H -0.4285 -0.6583 0.1443 0.023 Uiso 1 1 calc R U . . .
C20 C -0.5351(2) -0.4078(6) 0.19443(12) 0.0241(8) Uani 1 1 d . . . . .
H20 H -0.5847 -0.4052 0.2054 0.029 Uiso 1 1 calc R U . . .
O1 O -0.26239(18) 0.1845(3) 0.15294(8) 0.0197(5) Uani 1 1 d . . . . .
O2 O -0.21239(17) -0.2883(3) 0.08016(7) 0.0176(5) Uani 1 1 d . . . . .
C8 C -0.3231(2) -0.2397(4) 0.11807(9) 0.0107(5) Uani 1 1 d . . . . .
C7 C -0.3420(2) -0.0789(4) 0.14098(10) 0.0138(6) Uani 1 1 d . . . . .
C6 C -0.2736(2) 0.0466(4) 0.13711(9) 0.0137(6) Uani 1 1 d . . . . .
C9 C -0.2469(2) -0.1954(4) 0.10060(9) 0.0127(6) Uani 1 1 d . . . . .
H3 H -0.390(3) -0.026(6) 0.1305(13) 0.015(11) Uiso 1 1 d . . . . .
H8 H -0.367(3) -0.265(7) 0.0967(14) 0.020(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 Cu1 2.6036(5) . ?
I1 Cu1 2.6933(5) 5_565 ?
Cu1 N3 1.994(3) . ?
Cu1 N1 2.058(3) . ?
Cu1 Cu1 2.6381(8) 5_565 ?
Cu1 I1 2.6932(5) 5_565 ?
N1 C5 1.345(4) . ?
N1 C1 1.347(4) . ?
C5 C4 1.383(5) . ?
C5 H5 0.9500 . ?
C3 C4 1.391(5) . ?
C3 C2 1.400(4) . ?
C3 N2 1.425(4) . ?
C16 C15 1.388(5) . ?
C16 C11 1.408(5) . ?
C16 C17 1.515(4) . ?
N2 C9 1.410(4) . ?
N2 C6 1.417(4) . ?
C1 C2 1.386(5) . ?
C1 H1 0.9500 . ?
C2 H2 0.9500 . ?
C4 H4 0.9500 . ?
C12 C11 1.390(5) . ?
C12 C13 1.396(6) . ?
C12 H12 0.9500 . ?
C23 C22 1.385(5) . ?
C23 C18 1.400(5) . ?
C23 C17 1.520(5) . ?
N3 C24 1.137(5) . ?
C17 C8 1.565(4) . ?
C17 H17 1.0000 . ?
C10 C11 1.512(5) . ?
C10 C18 1.514(5) . ?
C10 C7 1.561(5) . ?
C10 H10 1.0000 . ?
C15 C14 1.400(5) . ?
C15 H15 0.9500 . ?
C18 C19 1.391(5) . ?
C24 C25 1.456(5) . ?
C19 C20 1.391(6) . ?
C19 H19 0.9500 . ?
C14 C13 1.383(6) . ?
C14 H14 0.9500 . ?
C21 C20 1.386(6) . ?
C21 C22 1.400(6) . ?
C21 H21 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C13 H13 0.9500 . ?
C22 H22 0.9500 . ?
C20 H20 0.9500 . ?
O1 C6 1.203(4) . ?
O2 C9 1.208(4) . ?
C8 C9 1.510(5) . ?
C8 C7 1.533(5) . ?
C8 H8 0.98(5) . ?
C7 C6 1.510(5) . ?
C7 H3 0.92(5) . ?

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
Cu1 I1 Cu1 59.715(16) . 5_565 ?
N3 Cu1 N1 106.88(12) . . ?
N3 Cu1 I1 110.07(9) . . ?
N1 Cu1 I1 110.09(8) . . ?
N3 Cu1 Cu1 127.10(9) . 5_565 ?
N1 Cu1 Cu1 125.39(9) . 5_565 ?
I1 Cu1 Cu1 61.832(18) . 5_565 ?
N3 Cu1 I1 105.02(9) . 5_565 ?
N1 Cu1 I1 103.60(8) . 5_565 ?
I1 Cu1 I1 120.286(16) . 5_565 ?
Cu1 Cu1 I1 58.454(17) 5_565 5_565 ?
C5 N1 C1 116.4(3) . . ?
C5 N1 Cu1 119.3(2) . . ?
C1 N1 Cu1 122.5(2) . . ?
N1 C5 C4 124.3(3) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C4 C3 C2 118.4(3) . . ?
C4 C3 N2 121.3(3) . . ?
C2 C3 N2 120.2(3) . . ?
C15 C16 C11 120.0(3) . . ?
C15 C16 C17 126.7(3) . . ?
C11 C16 C17 113.3(3) . . ?
C9 N2 C6 111.5(3) . . ?
C9 N2 C3 124.0(3) . . ?
C6 N2 C3 124.3(3) . . ?
N1 C1 C2 123.8(3) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.5(3) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C22 C23 C18 120.7(3) . . ?
C22 C23 C17 126.2(3) . . ?
C18 C23 C17 113.0(3) . . ?
C24 N3 Cu1 178.3(3) . . ?
C16 C17 C23 107.1(3) . . ?
C16 C17 C8 107.9(3) . . ?
C23 C17 C8 104.6(3) . . ?
C16 C17 H17 112.3 . . ?
C23 C17 H17 112.3 . . ?
C8 C17 H17 112.3 . . ?
C11 C10 C18 107.2(3) . . ?
C11 C10 C7 106.4(3) . . ?
C18 C10 C7 105.6(3) . . ?
C11 C10 H10 112.4 . . ?
C18 C10 H10 112.4 . . ?
C7 C10 H10 112.4 . . ?
C12 C11 C16 120.7(3) . . ?
C12 C11 C10 125.8(3) . . ?
C16 C11 C10 113.4(3) . . ?
C16 C15 C14 118.8(3) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C19 C18 C23 119.8(3) . . ?
C19 C18 C10 126.3(3) . . ?
C23 C18 C10 113.9(3) . . ?
N3 C24 C25 179.8(5) . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.2 . . ?
C13 C14 C15 121.2(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C20 C21 C22 120.6(4) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C23 C22 C21 119.0(4) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C9 C8 C7 105.4(3) . . ?
C9 C8 C17 112.2(3) . . ?
C7 C8 C17 109.7(3) . . ?
C9 C8 H8 108(3) . . ?
C7 C8 H8 112(3) . . ?
C17 C8 H8 110(3) . . ?
C6 C7 C8 105.4(3) . . ?
C6 C7 C10 112.5(3) . . ?
C8 C7 C10 110.5(3) . . ?
C6 C7 H3 107(3) . . ?
C8 C7 H3 112(3) . . ?
C10 C7 H3 109(3) . . ?
O1 C6 N2 124.7(3) . . ?
O1 C6 C7 126.8(3) . . ?
N2 C6 C7 108.5(3) . . ?
O2 C9 N2 125.1(3) . . ?
O2 C9 C8 126.1(3) . . ?
N2 C9 C8 108.8(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C5 C4 1.8(5) . . . . ?
Cu1 N1 C5 C4 -163.3(3) . . . . ?
C4 C3 N2 C9 -27.8(5) . . . . ?
C2 C3 N2 C9 148.1(3) . . . . ?
C4 C3 N2 C6 156.6(3) . . . . ?
C2 C3 N2 C6 -27.4(5) . . . . ?
C5 N1 C1 C2 -3.3(5) . . . . ?
Cu1 N1 C1 C2 161.3(3) . . . . ?
N1 C1 C2 C3 2.0(5) . . . . ?
C4 C3 C2 C1 1.0(5) . . . . ?
N2 C3 C2 C1 -175.1(3) . . . . ?
N1 C5 C4 C3 1.0(5) . . . . ?
C2 C3 C4 C5 -2.3(5) . . . . ?
N2 C3 C4 C5 173.7(3) . . . . ?
C15 C16 C17 C23 125.5(4) . . . . ?
C11 C16 C17 C23 -54.0(4) . . . . ?
C15 C16 C17 C8 -122.3(3) . . . . ?
C11 C16 C17 C8 58.1(3) . . . . ?
C22 C23 C17 C16 -126.4(4) . . . . ?
C18 C23 C17 C16 54.6(4) . . . . ?
C22 C23 C17 C8 119.3(4) . . . . ?
C18 C23 C17 C8 -59.7(3) . . . . ?
C13 C12 C11 C16 -0.6(5) . . . . ?
C13 C12 C11 C10 179.5(3) . . . . ?
C15 C16 C11 C12 0.1(5) . . . . ?
C17 C16 C11 C12 179.7(3) . . . . ?
C15 C16 C11 C10 -179.9(3) . . . . ?
C17 C16 C11 C10 -0.4(4) . . . . ?
C18 C10 C11 C12 -126.0(4) . . . . ?
C7 C10 C11 C12 121.5(4) . . . . ?
C18 C10 C11 C16 54.1(4) . . . . ?
C7 C10 C11 C16 -58.4(4) . . . . ?
C11 C16 C15 C14 0.3(5) . . . . ?
C17 C16 C15 C14 -179.2(3) . . . . ?
C22 C23 C18 C19 -0.5(5) . . . . ?
C17 C23 C18 C19 178.6(3) . . . . ?
C22 C23 C18 C10 -179.9(3) . . . . ?
C17 C23 C18 C10 -0.8(4) . . . . ?
C11 C10 C18 C19 127.1(4) . . . . ?
C7 C10 C18 C19 -119.8(4) . . . . ?
C11 C10 C18 C23 -53.6(4) . . . . ?
C7 C10 C18 C23 59.5(4) . . . . ?
C23 C18 C19 C20 0.7(5) . . . . ?
C10 C18 C19 C20 -180.0(3) . . . . ?
C16 C15 C14 C13 -0.4(5) . . . . ?
C15 C14 C13 C12 -0.1(6) . . . . ?
C11 C12 C13 C14 0.5(5) . . . . ?
C18 C23 C22 C21 -0.2(5) . . . . ?
C17 C23 C22 C21 -179.1(3) . . . . ?
C20 C21 C22 C23 0.6(5) . . . . ?
C22 C21 C20 C19 -0.3(6) . . . . ?
C18 C19 C20 C21 -0.3(6) . . . . ?
C16 C17 C8 C9 63.0(3) . . . . ?
C23 C17 C8 C9 176.8(3) . . . . ?
C16 C17 C8 C7 -53.9(3) . . . . ?
C23 C17 C8 C7 59.9(3) . . . . ?
C9 C8 C7 C6 -2.6(3) . . . . ?
C17 C8 C7 C6 118.4(3) . . . . ?
C9 C8 C7 C10 -124.4(3) . . . . ?
C17 C8 C7 C10 -3.3(4) . . . . ?
C11 C10 C7 C6 -58.8(3) . . . . ?
C18 C10 C7 C6 -172.5(3) . . . . ?
C11 C10 C7 C8 58.7(3) . . . . ?
C18 C10 C7 C8 -54.9(3) . . . . ?
C9 N2 C6 O1 174.0(3) . . . . ?
C3 N2 C6 O1 -10.0(5) . . . . ?
C9 N2 C6 C7 -5.8(4) . . . . ?
C3 N2 C6 C7 170.2(3) . . . . ?
C8 C7 C6 O1 -174.7(3) . . . . ?
C10 C7 C6 O1 -54.2(5) . . . . ?
C8 C7 C6 N2 5.1(3) . . . . ?
C10 C7 C6 N2 125.5(3) . . . . ?
C6 N2 C9 O2 -177.1(3) . . . . ?
C3 N2 C9 O2 6.9(5) . . . . ?
C6 N2 C9 C8 4.1(4) . . . . ?
C3 N2 C9 C8 -172.0(3) . . . . ?
C7 C8 C9 O2 -179.5(3) . . . . ?
C17 C8 C9 O2 61.1(4) . . . . ?
C7 C8 C9 N2 -0.7(3) . . . . ?
C17 C8 C9 N2 -120.1(3) . . . . ?

_refine_diff_density_max         2.041
_refine_diff_density_min         -1.759
_refine_diff_density_rms         0.145

