# Electronic Supplementary Material (ESI) for MedChemComm.
# 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. 
# 
#######################################################################

data_aaaa
_database_code_depnum_ccdc_archive 'CCDC 1587628'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2017-11-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H14 Cu N4 O8'
_chemical_formula_sum            'C18 H14 Cu N4 O8'
_chemical_formula_weight         477.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   10.093(3)
_cell_length_b                   10.384(3)
_cell_length_c                   10.818(3)
_cell_angle_alpha                78.634(4)
_cell_angle_beta                 65.151(4)
_cell_angle_gamma                71.085(4)
_cell_volume                     970.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4844
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.66
_cell_measurement_theta_min      2.31
_exptl_absorpt_coefficient_mu    1.181
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.635
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             486
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11785
_diffrn_reflns_theta_full        26.58
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         2.08
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3419
_reflns_number_total             4023
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.366
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0530P)²+0.2502P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0964
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 O5, N3
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 O3, Cu1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C7(H7), C5(H5), C6(H6),
 C1(H1), C2(H2), C3(H3)
3.b Idealised Me refined as rotating group:
 C18(H18a,H18b,H18c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Cu1 Cu 0.15759(3) 0.52341(3) 0.68722(3) 0.04423(11) Uani 1 d . . . U
O6 O 0.1476(2) 0.35267(17) 0.63407(17) 0.0556(4) Uani 1 d . . . .
O5 O 0.3776(2) 0.4324(2) 0.6326(2) 0.0678(5) Uani 1 d . . . U
O2 O -0.2587(2) 0.04012(19) 1.1112(2) 0.0756(6) Uani 1 d . . . .
O3 O 0.2823(3) 0.3994(2) 0.8501(2) 0.0769(6) Uani 1 d . . . U
O8 O 0.1964(4) 0.4934(2) 0.4603(2) 0.1018(9) Uani 1 d . . . .
O1 O -0.4713(2) 0.1584(2) 1.0802(3) 0.0871(7) Uani 1 d . . . .
O4 O 0.5167(3) 0.3017(3) 0.7373(3) 0.1030(9) Uani 1 d . . . .
O7 O 0.2142(4) 0.2869(2) 0.4343(2) 0.1074(10) Uani 1 d . . . .
N2 N -0.0576(2) 0.57369(18) 0.80179(17) 0.0397(4) Uani 1 d . . . .
N1 N 0.1798(2) 0.71094(19) 0.6609(2) 0.0484(5) Uani 1 d . . . .
N3 N 0.3927(2) 0.3779(2) 0.7456(3) 0.0533(5) Uani 1 d . . . U
N4 N 0.1876(3) 0.3771(2) 0.5054(2) 0.0670(6) Uani 1 d . . . .
C11 C -0.1312(2) 0.4667(2) 0.8683(2) 0.0402(5) Uani 1 d . . . .
C10 C -0.1410(3) 0.6973(2) 0.8131(2) 0.0431(5) Uani 1 d . . . .
H10 H -0.2443 0.7094 0.8639 0.052 Uiso 1 calc . . R .
C9 C 0.0613(3) 0.8272(2) 0.6855(2) 0.0423(5) Uani 1 d . . . .
C12 C -0.2681(3) 0.4729(2) 0.8649(2) 0.0462(5) Uani 1 d . . . .
H12 H -0.3140 0.5459 0.8180 0.055 Uiso 1 calc . . R .
C13 C -0.3362(3) 0.3694(2) 0.9319(3) 0.0497(5) Uani 1 d . . . .
H13 H -0.4298 0.3738 0.9320 0.060 Uiso 1 calc . . R .
C15 C -0.1271(3) 0.2517(2) 0.9988(2) 0.0498(5) Uani 1 d . . . .
H15 H -0.0791 0.1768 1.0423 0.060 Uiso 1 calc . . R .
C16 C -0.0592(3) 0.3560(2) 0.9338(2) 0.0464(5) Uani 1 d . . . .
H16 H 0.0341 0.3519 0.9341 0.056 Uiso 1 calc . . R .
C14 C -0.2659(3) 0.2587(2) 0.9991(2) 0.0466(5) Uani 1 d . . . .
C17 C -0.3454(3) 0.1499(3) 1.0677(3) 0.0581(6) Uani 1 d . . . .
C8 C -0.0917(3) 0.8202(2) 0.7550(2) 0.0427(5) Uani 1 d . . . .
C7 C -0.2063(3) 0.9407(2) 0.7752(3) 0.0567(6) Uani 1 d . . . .
H7 H -0.3063 0.9368 0.8216 0.068 Uiso 1 calc . . R .
C5 C -0.0333(4) 1.0763(3) 0.6663(3) 0.0623(7) Uani 1 d . . . .
H5 H -0.0142 1.1614 0.6383 0.075 Uiso 1 calc . . R .
C4 C 0.0894(3) 0.9570(2) 0.6429(3) 0.0529(6) Uani 1 d . . . .
C6 C -0.1779(4) 1.0683(3) 0.7287(3) 0.0662(7) Uani 1 d . . . .
H6 H -0.2581 1.1470 0.7407 0.079 Uiso 1 calc . . R .
C1 C 0.3199(3) 0.7243(3) 0.5999(3) 0.0725(9) Uani 1 d . . . .
H1 H 0.4002 0.6455 0.5836 0.087 Uiso 1 calc . . R .
C2 C 0.3535(4) 0.8492(3) 0.5589(4) 0.0854(10) Uani 1 d . . . .
H2 H 0.4539 0.8529 0.5184 0.102 Uiso 1 calc . . R .
C18 C -0.3285(5) -0.0700(3) 1.1777(4) 0.0975(12) Uani 1 d . . . .
H18A H -0.3473 -0.1056 1.1131 0.146 Uiso 1 calc . . GR .
H18B H -0.4226 -0.0364 1.2517 0.146 Uiso 1 calc . . GR .
H18C H -0.2617 -0.1412 1.2125 0.146 Uiso 1 calc . . GR .
C3 C 0.2400(4) 0.9647(3) 0.5782(3) 0.0725(8) Uani 1 d . . . .
H3 H 0.2610 1.0489 0.5491 0.087 Uiso 1 calc . . R .


_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 2.0128(18) . ?
Cu1 O5 1.9820(19) . ?
Cu1 O8 2.386(2) . ?
Cu1 N2 1.9448(19) . ?
Cu1 N1 1.984(2) . ?
O6 N4 1.273(3) . ?
O5 N3 1.290(3) . ?
O2 C17 1.332(3) . ?
O2 C18 1.447(3) . ?
O3 N3 1.204(3) . ?
O8 N4 1.227(3) . ?
O1 C17 1.196(3) . ?
O4 N3 1.221(3) . ?
O7 N4 1.219(3) . ?
N2 C11 1.440(3) . ?
N2 C10 1.283(3) . ?
N1 C9 1.372(3) . ?
N1 C1 1.327(3) . ?
C11 C12 1.378(3) . ?
C11 C16 1.387(3) . ?
C10 H10 0.9300 . ?
C10 C8 1.450(3) . ?
C9 C8 1.425(3) . ?
C9 C4 1.415(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.381(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.389(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.383(3) . ?
C15 C14 1.378(3) . ?
C16 H16 0.9300 . ?
C14 C17 1.491(3) . ?
C8 C7 1.382(3) . ?
C7 H7 0.9300 . ?
C7 C6 1.397(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.413(4) . ?
C5 C6 1.350(4) . ?
C4 C3 1.404(4) . ?
C6 H6 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.388(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.341(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C3 H3 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
O6 Cu1 O8 57.05(7) . . ?
O5 Cu1 O6 85.01(9) . . ?
O5 Cu1 O8 85.44(10) . . ?
O5 Cu1 N1 94.89(8) . . ?
N2 Cu1 O6 93.05(8) . . ?
N2 Cu1 O5 159.13(8) . . ?
N2 Cu1 O8 110.91(10) . . ?
N2 Cu1 N1 94.96(8) . . ?
N1 Cu1 O6 156.73(8) . . ?
N1 Cu1 O8 99.71(8) . . ?
N4 O6 Cu1 101.00(14) . . ?
N3 O5 Cu1 104.46(15) . . ?
C17 O2 C18 115.2(2) . . ?
N4 O8 Cu1 84.63(15) . . ?
C11 N2 Cu1 118.59(14) . . ?
C10 N2 Cu1 123.58(15) . . ?
C10 N2 C11 117.59(19) . . ?
C9 N1 Cu1 124.52(15) . . ?
C1 N1 Cu1 116.79(18) . . ?
C1 N1 C9 118.2(2) . . ?
O3 N3 O5 118.0(2) . . ?
O3 N3 O4 124.8(3) . . ?
O4 N3 O5 117.1(3) . . ?
O8 N4 O6 116.5(2) . . ?
O7 N4 O6 119.8(2) . . ?
O7 N4 O8 123.7(2) . . ?
C12 C11 N2 121.01(19) . . ?
C12 C11 C16 120.8(2) . . ?
C16 C11 N2 118.16(19) . . ?
N2 C10 H10 116.5 . . ?
N2 C10 C8 127.0(2) . . ?
C8 C10 H10 116.5 . . ?
N1 C9 C8 121.01(19) . . ?
N1 C9 C4 120.3(2) . . ?
C4 C9 C8 118.7(2) . . ?
C11 C12 H12 120.4 . . ?
C11 C12 C13 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(2) . . ?
C14 C13 H13 119.8 . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C14 C15 C16 120.1(2) . . ?
C11 C16 H16 120.2 . . ?
C15 C16 C11 119.5(2) . . ?
C15 C16 H16 120.2 . . ?
C13 C14 C17 117.4(2) . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 C17 122.7(2) . . ?
O2 C17 C14 112.3(2) . . ?
O1 C17 O2 123.4(2) . . ?
O1 C17 C14 124.2(2) . . ?
C9 C8 C10 126.3(2) . . ?
C7 C8 C10 115.3(2) . . ?
C7 C8 C9 118.4(2) . . ?
C8 C7 H7 118.7 . . ?
C8 C7 C6 122.6(3) . . ?
C6 C7 H7 118.7 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(2) . . ?
C5 C4 C9 120.0(2) . . ?
C3 C4 C9 118.9(2) . . ?
C3 C4 C5 121.1(2) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.8(3) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2 120.3 . . ?
O2 C18 H18A 109.5 . . ?
O2 C18 H18B 109.5 . . ?
O2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C4 C3 H3 120.3 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?

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
Cu1 O6 N4 O8 -9.9(3) . . . . ?
Cu1 O6 N4 O7 170.3(3) . . . . ?
Cu1 O5 N3 O3 -4.3(3) . . . . ?
Cu1 O5 N3 O4 171.7(2) . . . . ?
Cu1 O8 N4 O6 8.2(3) . . . . ?
Cu1 O8 N4 O7 -172.0(3) . . . . ?
Cu1 N2 C11 C12 -132.96(19) . . . . ?
Cu1 N2 C11 C16 45.9(2) . . . . ?
Cu1 N2 C10 C8 -5.7(3) . . . . ?
Cu1 N1 C9 C8 10.9(3) . . . . ?
Cu1 N1 C9 C4 -169.68(17) . . . . ?
Cu1 N1 C1 C2 171.8(3) . . . . ?
O6 Cu1 O5 N3 -96.64(16) . . . . ?
O6 Cu1 O8 N4 -5.53(18) . . . . ?
O6 Cu1 N2 C11 30.42(16) . . . . ?
O6 Cu1 N2 C10 -143.75(18) . . . . ?
O6 Cu1 N1 C9 92.5(3) . . . . ?
O6 Cu1 N1 C1 -79.0(3) . . . . ?
O5 Cu1 O6 N4 -82.39(18) . . . . ?
O5 Cu1 O8 N4 81.5(2) . . . . ?
O5 Cu1 N2 C11 -53.6(3) . . . . ?
O5 Cu1 N2 C10 132.3(2) . . . . ?
O5 Cu1 N1 C9 -178.76(19) . . . . ?
O5 Cu1 N1 C1 9.8(2) . . . . ?
O8 Cu1 O6 N4 5.41(17) . . . . ?
O8 Cu1 O5 N3 -153.91(16) . . . . ?
O8 Cu1 N2 C11 86.17(16) . . . . ?
O8 Cu1 N2 C10 -88.00(18) . . . . ?
O8 Cu1 N1 C9 95.0(2) . . . . ?
O8 Cu1 N1 C1 -76.4(2) . . . . ?
N2 Cu1 O6 N4 118.45(17) . . . . ?
N2 Cu1 O5 N3 -11.2(3) . . . . ?
N2 Cu1 O8 N4 -85.2(2) . . . . ?
N2 Cu1 N1 C9 -17.19(19) . . . . ?
N2 Cu1 N1 C1 171.3(2) . . . . ?
N2 C11 C12 C13 -178.9(2) . . . . ?
N2 C11 C16 C15 179.9(2) . . . . ?
N2 C10 C8 C9 -6.6(4) . . . . ?
N2 C10 C8 C7 176.0(2) . . . . ?
N1 Cu1 O6 N4 8.4(3) . . . . ?
N1 Cu1 O5 N3 106.72(16) . . . . ?
N1 Cu1 O8 N4 175.7(2) . . . . ?
N1 Cu1 N2 C11 -171.45(15) . . . . ?
N1 Cu1 N2 C10 14.38(19) . . . . ?
N1 C9 C8 C10 3.5(3) . . . . ?
N1 C9 C8 C7 -179.2(2) . . . . ?
N1 C9 C4 C5 178.8(2) . . . . ?
N1 C9 C4 C3 -1.4(4) . . . . ?
N1 C1 C2 C3 -1.5(6) . . . . ?
C11 N2 C10 C8 -180.0(2) . . . . ?
C11 C12 C13 C14 -1.5(4) . . . . ?
C10 N2 C11 C12 41.6(3) . . . . ?
C10 N2 C11 C16 -139.6(2) . . . . ?
C10 C8 C7 C6 178.5(2) . . . . ?
C9 N1 C1 C2 -0.3(5) . . . . ?
C9 C8 C7 C6 0.8(4) . . . . ?
C9 C4 C3 C2 -0.3(5) . . . . ?
C12 C11 C16 C15 -1.2(3) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 C17 -179.2(2) . . . . ?
C13 C14 C17 O2 170.7(2) . . . . ?
C13 C14 C17 O1 -7.9(4) . . . . ?
C15 C14 C17 O2 -8.3(4) . . . . ?
C15 C14 C17 O1 173.1(3) . . . . ?
C16 C11 C12 C13 2.3(3) . . . . ?
C16 C15 C14 C13 1.2(4) . . . . ?
C16 C15 C14 C17 -179.8(2) . . . . ?
C14 C15 C16 C11 -0.5(4) . . . . ?
C8 C9 C4 C5 -1.8(3) . . . . ?
C8 C9 C4 C3 178.0(2) . . . . ?
C8 C7 C6 C5 -2.8(4) . . . . ?
C5 C4 C3 C2 179.4(3) . . . . ?
C4 C9 C8 C10 -175.9(2) . . . . ?
C4 C9 C8 C7 1.4(3) . . . . ?
C4 C5 C6 C7 2.4(4) . . . . ?
C6 C5 C4 C9 -0.1(4) . . . . ?
C6 C5 C4 C3 -179.9(3) . . . . ?
C1 N1 C9 C8 -177.7(2) . . . . ?
C1 N1 C9 C4 1.7(4) . . . . ?
C1 C2 C3 C4 1.7(6) . . . . ?
C18 O2 C17 O1 -0.9(5) . . . . ?
C18 O2 C17 C14 -179.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_aaaaa
_database_code_depnum_ccdc_archive 'CCDC 1587630'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2016-06-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H16 Cl2 Cu N2 O2'
_chemical_formula_sum            'C19 H16 Cl2 Cu N2 O2'
_chemical_formula_weight         438.78
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.784(8)
_cell_length_b                   12.520(11)
_cell_length_c                   15.403(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.907(13)
_cell_angle_gamma                90.00
_cell_volume                     1846(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7848
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.439
_cell_measurement_theta_min      2.273
_exptl_absorpt_coefficient_mu    1.488
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             892
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            21771
_diffrn_reflns_theta_full        26.52
_diffrn_reflns_theta_max         26.52
_diffrn_reflns_theta_min         2.11
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                3270
_reflns_number_total             3793
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0350P)²+0.6780P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0670
_refine_ls_wR_factor_ref         0.0709
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C12(H12), C13(H13), C16(H16), C1(H1), C5(H5), C3(H3), C15(H15),
 C7(H7), C2(H2), C6(H6)
2.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.11070(2) 0.337707(17) 0.087815(14) 0.02788(8) Uani 1 d . . .
Cl1 Cl 0.04548(5) 0.36413(5) -0.05786(3) 0.04297(14) Uani 1 d . . .
Cl2 Cl 0.30133(5) 0.43888(4) 0.12141(4) 0.04612(14) Uani 1 d . . .
C10 C 0.1336(2) 0.17539(15) 0.22437(13) 0.0330(4) Uani 1 d . . .
H10 H 0.1807 0.1193 0.2572 0.040 Uiso 1 calc . . R
N1 N -0.07497(16) 0.32761(12) 0.12063(10) 0.0292(3) Uani 1 d . . .
N2 N 0.18722(15) 0.21282(12) 0.16148(10) 0.0285(3) Uani 1 d . . .
C11 C 0.31493(19) 0.16814(14) 0.14476(12) 0.0296(4) Uani 1 d . . .
O2 O 0.71799(15) 0.10176(13) 0.00763(11) 0.0511(4) Uani 1 d . . .
C12 C 0.4166(2) 0.12262(17) 0.21083(13) 0.0382(4) Uani 1 d . . .
H12 H 0.4021 0.1169 0.2685 0.046 Uiso 1 calc . . R
C13 C 0.5396(2) 0.08585(17) 0.19029(14) 0.0405(5) Uani 1 d . . .
H13 H 0.6068 0.0540 0.2342 0.049 Uiso 1 calc . . R
C16 C 0.3360(2) 0.17423(16) 0.05850(13) 0.0349(4) Uani 1 d . . .
H16 H 0.2664 0.2021 0.0138 0.042 Uiso 1 calc . . R
C8 C 0.0060(2) 0.21234(15) 0.24932(12) 0.0319(4) Uani 1 d . . .
C1 C -0.1780(2) 0.38466(17) 0.07220(14) 0.0372(4) Uani 1 d . . .
H1 H -0.1647 0.4130 0.0188 0.045 Uiso 1 calc . . R
C5 C -0.2395(2) 0.25770(17) 0.30976(14) 0.0408(5) Uani 1 d . . .
H5 H -0.3201 0.2735 0.3304 0.049 Uiso 1 calc . . R
C4 C -0.2200(2) 0.30318(15) 0.22920(13) 0.0336(4) Uani 1 d . . .
C3 C -0.3251(2) 0.36536(18) 0.17605(15) 0.0425(5) Uani 1 d . . .
H3 H -0.4077 0.3797 0.1948 0.051 Uiso 1 calc . . R
C15 C 0.4603(2) 0.13902(17) 0.03862(14) 0.0380(5) Uani 1 d . . .
H15 H 0.4744 0.1442 -0.0191 0.046 Uiso 1 calc . . R
C7 C -0.0214(2) 0.16856(16) 0.32680(14) 0.0407(5) Uani 1 d . . .
H7 H 0.0438 0.1222 0.3595 0.049 Uiso 1 calc . . R
C14 C 0.5638(2) 0.09597(15) 0.10501(14) 0.0349(4) Uani 1 d . . .
O1 O 0.79121(17) 0.01620(15) 0.13653(12) 0.0623(5) Uani 1 d . . .
C2 C -0.3052(2) 0.40423(18) 0.09736(15) 0.0439(5) Uani 1 d . . .
H2 H -0.3750 0.4433 0.0607 0.053 Uiso 1 calc . . R
C6 C -0.1423(2) 0.19127(18) 0.35758(15) 0.0440(5) Uani 1 d . . .
H6 H -0.1565 0.1613 0.4103 0.053 Uiso 1 calc . . R
C17 C 0.7031(2) 0.06527(17) 0.08681(16) 0.0430(5) Uani 1 d . . .
C18 C 0.8485(2) 0.0773(2) -0.01880(18) 0.0576(7) Uani 1 d . . .
H18A H 0.8672 0.0012 -0.0135 0.069 Uiso 1 calc . . R
H18B H 0.9251 0.1149 0.0190 0.069 Uiso 1 calc . . R
C9 C -0.09532(19) 0.28290(14) 0.19875(12) 0.0281(4) Uani 1 d . . .
C19 C 0.8354(3) 0.1118(3) -0.1127(2) 0.0775(9) Uani 1 d . . .
H19A H 0.7568 0.0768 -0.1491 0.116 Uiso 1 calc . . GR
H19B H 0.9189 0.0931 -0.1328 0.116 Uiso 1 calc . . GR
H19C H 0.8222 0.1878 -0.1167 0.116 Uiso 1 calc . . GR


_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 Cl1 2.2272(19) . ?
Cu1 Cl2 2.2255(15) . ?
Cu1 N1 1.987(2) . ?
Cu1 N2 1.9855(19) . ?
C10 N2 1.282(2) . ?
C10 C8 1.455(3) . ?
N1 C1 1.331(3) . ?
N1 C9 1.378(2) . ?
N2 C11 1.440(2) . ?
C11 C12 1.390(3) . ?
C11 C16 1.388(3) . ?
O2 C17 1.338(3) . ?
O2 C18 1.451(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.388(3) . ?
C16 C15 1.386(3) . ?
C8 C7 1.389(3) . ?
C8 C9 1.432(3) . ?
C1 C2 1.399(3) . ?
C5 C4 1.414(3) . ?
C5 C6 1.360(3) . ?
C4 C3 1.409(3) . ?
C4 C9 1.417(3) . ?
C3 C2 1.357(3) . ?
C15 C14 1.391(3) . ?
C7 C6 1.392(3) . ?
C14 C17 1.497(3) . ?
O1 C17 1.198(3) . ?
C18 C19 1.489(4) . ?

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
Cl2 Cu1 Cl1 101.64(3) . . ?
N1 Cu1 Cl1 100.30(6) . . ?
N1 Cu1 Cl2 138.00(6) . . ?
N2 Cu1 Cl1 133.52(5) . . ?
N2 Cu1 Cl2 96.67(7) . . ?
N2 Cu1 N1 93.51(7) . . ?
N2 C10 C8 126.19(17) . . ?
C1 N1 Cu1 116.71(14) . . ?
C1 N1 C9 118.56(16) . . ?
C9 N1 Cu1 123.51(12) . . ?
C10 N2 Cu1 123.71(13) . . ?
C10 N2 C11 119.92(16) . . ?
C11 N2 Cu1 116.27(12) . . ?
C12 C11 N2 123.01(18) . . ?
C16 C11 N2 117.10(16) . . ?
C16 C11 C12 119.88(18) . . ?
C17 O2 C18 116.83(18) . . ?
C13 C12 C11 119.57(19) . . ?
C12 C13 C14 120.80(18) . . ?
C15 C16 C11 120.29(18) . . ?
C7 C8 C10 115.44(18) . . ?
C7 C8 C9 118.44(18) . . ?
C9 C8 C10 125.99(17) . . ?
N1 C1 C2 123.55(19) . . ?
C6 C5 C4 121.05(19) . . ?
C5 C4 C9 119.99(18) . . ?
C3 C4 C5 121.18(18) . . ?
C3 C4 C9 118.78(18) . . ?
C2 C3 C4 119.67(19) . . ?
C16 C15 C14 120.0(2) . . ?
C8 C7 C6 122.7(2) . . ?
C13 C14 C15 119.36(19) . . ?
C13 C14 C17 119.58(18) . . ?
C15 C14 C17 121.0(2) . . ?
C3 C2 C1 118.96(19) . . ?
C5 C6 C7 119.3(2) . . ?
O2 C17 C14 110.94(18) . . ?
O1 C17 O2 124.0(2) . . ?
O1 C17 C14 125.1(2) . . ?
O2 C18 C19 107.9(2) . . ?
N1 C9 C8 121.13(16) . . ?
N1 C9 C4 120.36(17) . . ?
C4 C9 C8 118.48(17) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_1-6
_database_code_depnum_ccdc_archive 'CCDC 1587631'
_audit_update_record             
;
2017-11-26 deposited with the CCDC.
2018-09-19 downloaded from the CCDC.
;
_audit_creation_date             2017-11-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.25 svn.r3337 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C38 H32 Cu2 N4 O12 S2, 2(O)'
_chemical_formula_sum            'C38 H32 Cu2 N4 O14 S2'
_chemical_formula_weight         959.88
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.818(5)
_cell_length_b                   9.995(6)
_cell_length_c                   13.151(7)
_cell_angle_alpha                99.756(9)
_cell_angle_beta                 104.779(8)
_cell_angle_gamma                103.630(8)
_cell_volume                     1056.2(10)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2694
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      24.78
_cell_measurement_theta_min      2.16
_exptl_absorpt_coefficient_mu    1.175
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             490
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0704
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8547
_diffrn_reflns_theta_full        25.44
_diffrn_reflns_theta_max         25.44
_diffrn_reflns_theta_min         1.65
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2867
_reflns_number_total             3853
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XH (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.657
_refine_diff_density_min         -0.516
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3853
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0909
_refine_ls_R_factor_gt           0.0682
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1599P)²+0.1851P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2084
_refine_ls_wR_factor_ref         0.2307
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: O7(0.5) O8(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C13(H13),
 C15(H15), C16(H16)
3.c Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cu1 Cu 0.27502(8) 0.83177(7) 0.97864(5) 0.0320(3) Uani 1 d . . .
S1 S 0.51003(16) 0.82751(14) 0.89586(11) 0.0314(4) Uani 1 d . . .
O1 O 0.4956(5) 0.7984(4) 1.0021(3) 0.0372(9) Uani 1 d . . .
O2 O 0.3510(5) 0.8571(5) 0.8512(3) 0.0411(10) Uani 1 d . . .
O3 O 0.5252(5) 0.7053(4) 0.8285(4) 0.0440(10) Uani 1 d . . .
O4 O 0.6509(5) 0.9505(4) 0.9155(3) 0.0424(10) Uani 1 d . . .
O5 O -0.2246(8) 1.0173(8) 0.4803(5) 0.0824(18) Uani 1 d . . .
O6 O -0.0296(11) 1.2179(8) 0.5778(5) 0.097(2) Uani 1 d . . .
O7 O -0.404(3) 0.514(2) 0.4476(19) 0.185(12) Uani 0.50 d A 2 .
O8 O -0.119(2) 0.481(2) 0.4774(18) 0.159(9) Uani 0.50 d B 1 .
N1 N 0.0456(6) 0.8184(5) 0.9086(4) 0.0326(10) Uani 1 d . . .
N2 N 0.2307(6) 0.7487(6) 1.0981(4) 0.0404(12) Uani 1 d . . .
C1 C 0.3606(9) 0.7574(8) 1.1771(5) 0.0536(17) Uani 1 d . . .
H1 H 0.4622 0.8103 1.1764 0.064 Uiso 1 calc . . R
C2 C 0.3554(10) 0.6920(10) 1.2623(7) 0.067(2) Uani 1 d . . .
H2 H 0.4508 0.7002 1.3166 0.081 Uiso 1 calc . . R
C3 C 0.2057(10) 0.6155(9) 1.2632(6) 0.061(2) Uani 1 d . . .
H3 H 0.1983 0.5687 1.3180 0.073 Uiso 1 calc . . R
C4 C 0.0646(9) 0.6072(7) 1.1828(6) 0.0475(16) Uani 1 d . . .
C5 C -0.0959(10) 0.5310(8) 1.1816(6) 0.0561(19) Uani 1 d . . .
H5 H -0.1059 0.4828 1.2353 0.067 Uiso 1 calc . . R
C6 C -0.2298(10) 0.5274(7) 1.1064(7) 0.0576(19) Uani 1 d . . .
H6 H -0.3321 0.4768 1.1076 0.069 Uiso 1 calc . . R
C7 C -0.2181(8) 0.5996(7) 1.0249(6) 0.0480(16) Uani 1 d . . .
H7 H -0.3135 0.5976 0.9732 0.058 Uiso 1 calc . . R
C8 C -0.0671(7) 0.6741(6) 1.0198(5) 0.0370(13) Uani 1 d . . .
C9 C 0.0776(8) 0.6770(6) 1.0992(5) 0.0373(13) Uani 1 d . . .
C10 C -0.0736(7) 0.7486(6) 0.9340(5) 0.0352(13) Uani 1 d . . .
H10 H -0.1778 0.7448 0.8925 0.042 Uiso 1 calc . . R
C11 C 0.0071(7) 0.8839(6) 0.8180(5) 0.0351(13) Uani 1 d . . .
C12 C 0.1016(8) 1.0185(6) 0.8286(5) 0.0400(14) Uani 1 d . . .
H12 H 0.1905 1.0640 0.8905 0.048 Uiso 1 calc . . R
C13 C 0.0633(9) 1.0862(7) 0.7460(6) 0.0487(16) Uani 1 d . . .
H13 H 0.1254 1.1784 0.7530 0.058 Uiso 1 calc . . R
C14 C -0.0663(9) 1.0175(8) 0.6539(5) 0.0472(16) Uani 1 d . . .
C15 C -0.1549(9) 0.8820(9) 0.6425(6) 0.0574(19) Uani 1 d . . .
H15 H -0.2389 0.8342 0.5785 0.069 Uiso 1 calc . . R
C16 C -0.1207(8) 0.8133(8) 0.7269(6) 0.0518(17) Uani 1 d . . .
H16 H -0.1839 0.7217 0.7206 0.062 Uiso 1 calc . . R
C17 C -0.1011(10) 1.0962(9) 0.5686(6) 0.0583(19) Uani 1 d . . .
C18 C -0.2827(12) 1.0873(13) 0.3956(7) 0.084(3) Uani 1 d . . .
H18A H -0.2026 1.1777 0.4063 0.101 Uiso 1 calc . . R
H18B H -0.2965 1.0288 0.3251 0.101 Uiso 1 calc . . R
C19 C -0.4360(15) 1.1096(16) 0.3993(10) 0.114(4) Uani 1 d . . .
H19A H -0.5023 1.1034 0.3274 0.171 Uiso 1 calc . . GR
H19B H -0.4164 1.2018 0.4446 0.171 Uiso 1 calc . . GR
H19C H -0.4922 1.0383 0.4285 0.171 Uiso 1 calc . . GR


_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 S1 2.5803(18) . ?
Cu1 O1 2.006(4) . ?
Cu1 O2 1.989(4) . ?
Cu1 O4 2.223(4) 2_677 ?
Cu1 N1 1.959(5) . ?
Cu1 N2 1.978(5) . ?
S1 O1 1.504(4) . ?
S1 O2 1.495(4) . ?
S1 O3 1.438(4) . ?
S1 O4 1.459(4) . ?
O4 Cu1 2.223(4) 2_677 ?
O5 C17 1.340(10) . ?
O5 C18 1.461(9) . ?
O6 C17 1.201(11) . ?
N1 C10 1.272(7) . ?
N1 C11 1.458(7) . ?
N2 C1 1.310(8) . ?
N2 C9 1.376(8) . ?
C1 C2 1.394(10) . ?
C2 C3 1.365(11) . ?
C3 C4 1.387(10) . ?
C4 C5 1.435(10) . ?
C4 C9 1.413(8) . ?
C5 C6 1.321(11) . ?
C6 C7 1.402(10) . ?
C7 C8 1.388(8) . ?
C8 C9 1.419(9) . ?
C8 C10 1.449(8) . ?
C11 C12 1.368(9) . ?
C11 C16 1.361(9) . ?
C12 C13 1.386(8) . ?
C13 C14 1.374(10) . ?
C14 C15 1.356(11) . ?
C14 C17 1.486(9) . ?
C15 C16 1.407(10) . ?
C18 C19 1.432(13) . ?

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
O1 Cu1 S1 35.59(12) . . ?
O1 Cu1 O4 99.67(17) . 2_677 ?
O2 Cu1 S1 35.27(12) . . ?
O2 Cu1 O1 70.85(16) . . ?
O2 Cu1 O4 104.76(18) . 2_677 ?
O4 Cu1 S1 104.67(11) 2_677 . ?
N1 Cu1 S1 129.91(14) . . ?
N1 Cu1 O1 160.31(19) . . ?
N1 Cu1 O2 96.00(18) . . ?
N1 Cu1 O4 97.84(18) . 2_677 ?
N1 Cu1 N2 94.9(2) . . ?
N2 Cu1 S1 128.31(15) . . ?
N2 Cu1 O1 93.84(19) . . ?
N2 Cu1 O2 159.6(2) . . ?
N2 Cu1 O4 90.7(2) . 2_677 ?
O1 S1 Cu1 50.90(15) . . ?
O2 S1 Cu1 50.22(16) . . ?
O2 S1 O1 101.1(2) . . ?
O3 S1 Cu1 125.72(19) . . ?
O3 S1 O1 110.5(3) . . ?
O3 S1 O2 112.3(3) . . ?
O3 S1 O4 110.5(2) . . ?
O4 S1 Cu1 123.71(17) . . ?
O4 S1 O1 109.8(2) . . ?
O4 S1 O2 112.2(3) . . ?
S1 O1 Cu1 93.5(2) . . ?
S1 O2 Cu1 94.5(2) . . ?
S1 O4 Cu1 131.5(2) . 2_677 ?
C17 O5 C18 117.8(8) . . ?
C10 N1 Cu1 123.3(4) . . ?
C10 N1 C11 117.7(5) . . ?
C11 N1 Cu1 118.9(4) . . ?
C1 N2 Cu1 115.4(4) . . ?
C1 N2 C9 119.7(5) . . ?
C9 N2 Cu1 124.7(4) . . ?
N2 C1 C2 123.8(7) . . ?
C3 C2 C1 117.8(7) . . ?
C2 C3 C4 120.3(6) . . ?
C3 C4 C5 122.4(6) . . ?
C3 C4 C9 119.3(6) . . ?
C9 C4 C5 118.3(6) . . ?
C6 C5 C4 121.9(6) . . ?
C5 C6 C7 120.2(7) . . ?
C8 C7 C6 121.3(7) . . ?
C7 C8 C9 119.0(6) . . ?
C7 C8 C10 115.4(6) . . ?
C9 C8 C10 125.6(5) . . ?
N2 C9 C4 119.1(6) . . ?
N2 C9 C8 121.6(5) . . ?
C4 C9 C8 119.4(6) . . ?
N1 C10 C8 128.0(5) . . ?
C12 C11 N1 117.9(5) . . ?
C16 C11 N1 120.5(6) . . ?
C16 C11 C12 121.6(6) . . ?
C11 C12 C13 119.3(6) . . ?
C14 C13 C12 120.1(7) . . ?
C13 C14 C17 117.4(7) . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 C17 122.5(7) . . ?
C14 C15 C16 120.5(7) . . ?
C11 C16 C15 118.4(7) . . ?
O5 C17 C14 112.5(7) . . ?
O6 C17 O5 123.2(7) . . ?
O6 C17 C14 124.3(8) . . ?
C19 C18 O5 109.6(8) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
