# 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 2016

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

data_be02je1n
_database_code_depnum_ccdc_archive 'CCDC 855225'
_audit_update_record             
;
2011-11-22 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;
#TrackingRef 'ccdc_deposit C68 H54.24 Cu2 N4 O11.12 S4.cif'


_audit_creation_date             2011-02-11T11:26:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C68 H52 Cu2 N4 O10 S4, 1.12(H2 O)'
_chemical_formula_sum            'C68 H54.24 Cu2 N4 O11.12 S4'
_chemical_formula_weight         1360.66
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
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                   19.4562(31)
_cell_length_b                   15.7960(25)
_cell_length_c                   10.1007(16)
_cell_angle_alpha                90.000
_cell_angle_beta                 103.170(2)
_cell_angle_gamma                90.000
_cell_volume                     3022.6(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3929
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      23.16
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.19
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1402.1
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.909
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.8023
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'BRUKER SADABS'

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromador  graphite
_diffrn_measurement_device_type  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0509
_diffrn_reflns_number            24837
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.68
_diffrn_reflns_theta_max         26.00
_reflns_number_total             5953
_reflns_number_gt                4434
_reflns_threshold_expression     >2σ(I)
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.999


#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#
_computing_data_collection       'BRUKER Smart'
_computing_cell_refinement       'BRUKER Smart'
_computing_data_reduction        'BRUKER Saint'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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 > 2σ(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.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0473P)²+3.7858P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5953
_refine_ls_number_parameters     518
_refine_ls_number_restraints     453
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1123
_refine_ls_wR_factor_gt          0.0991
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.545
_refine_diff_density_rms         0.081

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'
Cl Cl 0.1484 0.1585 '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'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.049976(18) 0.04906(2) 0.06584(3) 0.01584(11) Uani 1 1 d . . .
N1 N 0.26323(13) -0.20220(16) -0.0700(3) 0.0226(6) Uani 1 1 d . . .
C2 C 0.23840(17) -0.2693(2) -0.1459(3) 0.0245(7) Uani 1 1 d . . .
H2 H 0.2714 -0.3047 -0.1754 0.029 Uiso 1 1 calc R . .
C3 C 0.16823(16) -0.29049(19) -0.1842(3) 0.0214(7) Uani 1 1 d . . .
H3 H 0.1529 -0.3396 -0.2370 0.026 Uiso 1 1 calc R . .
C4 C 0.12105(16) -0.23765(18) -0.1430(3) 0.0181(6) Uani 1 1 d . . .
H4 H 0.0721 -0.2501 -0.1678 0.022 Uiso 1 1 calc R . .
C5 C 0.14408(15) -0.16682(18) -0.0658(3) 0.0153(6) Uani 1 1 d . . .
C6 C 0.21720(15) -0.15079(18) -0.0298(3) 0.0177(6) Uani 1 1 d . . .
C7 C 0.09017(15) -0.10776(19) -0.0338(3) 0.0168(6) Uani 1 1 d . . .
O8 O 0.11253(10) -0.04234(13) 0.0339(2) 0.0209(5) Uani 1 1 d . . .
O9 O 0.02631(11) -0.12659(13) -0.0786(2) 0.0223(5) Uani 1 1 d . . .
S10 S 0.25313(4) -0.06246(5) 0.06911(8) 0.02111(18) Uani 1 1 d D . .
C11 C 0.34491(15) -0.0727(2) 0.0602(3) 0.0287(8) Uani 1 1 d D . .
H11A H 0.3618 -0.1305 0.0879 0.034 Uiso 1 1 calc R . .
H11B H 0.3491 -0.0636 -0.0345 0.034 Uiso 1 1 calc R . .
C12 C 0.38935(15) -0.00928(18) 0.1520(3) 0.0237(7) Uani 1 1 d D . .
C13 C 0.38896(16) -0.0061(2) 0.2913(3) 0.0294(8) Uani 1 1 d D . .
H13 H 0.3568 -0.0406 0.3251 0.035 Uiso 1 1 calc R . .
C14 C 0.43420(17) 0.0457(2) 0.3783(3) 0.0302(8) Uani 1 1 d D . .
H14 H 0.4328 0.0471 0.4717 0.036 Uiso 1 1 calc R . .
C15 C 0.48276(16) 0.0972(2) 0.3320(3) 0.0281(8) Uani 1 1 d D . .
C16 C 0.53268(19) 0.1483(2) 0.4211(3) 0.0418(10) Uani 1 1 d D . .
H16 H 0.5328 0.1504 0.5151 0.050 Uiso 1 1 calc R . .
C17 C 0.5804(2) 0.1944(3) 0.3727(4) 0.0572(13) Uani 1 1 d D . .
H17 H 0.6146 0.2270 0.4338 0.069 Uiso 1 1 calc R . .
C18 C 0.5799(2) 0.1946(3) 0.2341(4) 0.0598(13) Uani 1 1 d D . .
H18 H 0.6129 0.2282 0.2016 0.072 Uiso 1 1 calc R . .
C19 C 0.53193(18) 0.1464(2) 0.1448(3) 0.0407(9) Uani 1 1 d D . .
H19 H 0.5318 0.1471 0.0507 0.049 Uiso 1 1 calc R . .
C20 C 0.48278(16) 0.09577(19) 0.1920(3) 0.0258(7) Uani 1 1 d D . .
C21 C 0.43439(15) 0.04232(19) 0.1046(3) 0.0251(7) Uani 1 1 d D . .
H21 H 0.4332 0.0424 0.0101 0.030 Uiso 1 1 calc R . .
N31 N 0.02775(15) -0.13616(17) 0.5840(3) 0.0264(6) Uani 1 1 d . . .
C32 C -0.02712(18) -0.1863(2) 0.5827(3) 0.0289(8) Uani 1 1 d . . .
H32 H -0.0313 -0.2103 0.6666 0.035 Uiso 1 1 calc R . .
C33 C -0.07820(17) -0.2060(2) 0.4687(3) 0.0247(7) Uani 1 1 d . . .
H33 H -0.1159 -0.2433 0.4728 0.030 Uiso 1 1 calc R . .
C34 C -0.07235(16) -0.16918(19) 0.3485(3) 0.0213(7) Uani 1 1 d . . .
H34 H -0.1063 -0.1816 0.2671 0.026 Uiso 1 1 calc R . .
C35 C -0.01735(16) -0.11399(18) 0.3446(3) 0.0186(6) Uani 1 1 d . . .
C36 C 0.03291(16) -0.10000(19) 0.4672(3) 0.0202(7) Uani 1 1 d . A .
C37 C -0.01338(16) -0.07342(19) 0.2145(3) 0.0195(7) Uani 1 1 d . . .
O38 O 0.03159(11) -0.01567(14) 0.2189(2) 0.0247(5) Uani 1 1 d . . .
O39 O -0.05584(11) -0.09883(13) 0.1075(2) 0.0220(5) Uani 1 1 d . . .
S40 S 0.10790(4) -0.03516(5) 0.47579(8) 0.02412(19) Uani 1 1 d . . .
C41B C 0.1504(2) -0.0577(3) 0.6560(6) 0.0170(13) Uani 0.559(3) 1 d PDU A 1
H41C H 0.1216 -0.0353 0.7171 0.020 Uiso 0.559(3) 1 calc PR A 1
H41D H 0.1567 -0.1193 0.6714 0.020 Uiso 0.559(3) 1 calc PR A 1
C42B C 0.2203(4) -0.0137(6) 0.6803(14) 0.0216(14) Uani 0.559(3) 1 d PDU A 1
C43B C 0.2764(2) -0.0490(3) 0.6320(6) 0.0273(12) Uani 0.559(3) 1 d PDU A 1
H43B H 0.2699 -0.1015 0.5849 0.033 Uiso 0.559(3) 1 calc PR A 1
C44B C 0.3401(2) -0.0088(3) 0.6521(6) 0.0289(13) Uani 0.559(3) 1 d PDU A 1
H44B H 0.3770 -0.0335 0.6179 0.035 Uiso 0.559(3) 1 calc PR A 1
C45B C 0.3518(2) 0.0685(3) 0.7224(6) 0.0268(14) Uani 0.559(3) 1 d PDU A 1
C46B C 0.4163(2) 0.1133(3) 0.7398(6) 0.0335(14) Uani 0.559(3) 1 d PDU A 1
H46B H 0.4541 0.0900 0.7067 0.040 Uiso 0.559(3) 1 calc PR A 1
C47B C 0.4242(3) 0.1894(3) 0.8036(7) 0.0477(16) Uani 0.559(3) 1 d PDU A 1
H47B H 0.4667 0.2203 0.8103 0.057 Uiso 0.559(3) 1 calc PR A 1
C48B C 0.3708(3) 0.2229(4) 0.8597(9) 0.0484(18) Uani 0.559(3) 1 d PDU A 1
H48B H 0.3781 0.2750 0.9075 0.058 Uiso 0.559(3) 1 calc PR A 1
C49B C 0.3080(3) 0.1808(3) 0.8460(7) 0.0446(14) Uani 0.559(3) 1 d PDU A 1
H49B H 0.2719 0.2041 0.8842 0.053 Uiso 0.559(3) 1 calc PR A 1
C50B C 0.2967(2) 0.1031(3) 0.7754(7) 0.0317(13) Uani 0.559(3) 1 d PDU A 1
C51B C 0.2319(2) 0.0591(4) 0.7541(8) 0.0274(15) Uani 0.559(3) 1 d PDU A 1
H51B H 0.1954 0.0810 0.7924 0.033 Uiso 0.559(3) 1 calc PR A 1
C41C C 0.1727(4) -0.0720(5) 0.6241(8) 0.032(2) Uani 0.441(3) 1 d PDU A 2
H41E H 0.1484 -0.0897 0.6955 0.038 Uiso 0.441(3) 1 calc PR A 2
H41F H 0.1978 -0.1217 0.5989 0.038 Uiso 0.441(3) 1 calc PR A 2
C42C C 0.2248(6) -0.0036(9) 0.6783(17) 0.0270(17) Uani 0.441(3) 1 d PDU A 2
C43C C 0.2850(3) 0.0083(5) 0.6252(7) 0.0376(16) Uani 0.441(3) 1 d PDU A 2
H43C H 0.2924 -0.0274 0.5541 0.045 Uiso 0.441(3) 1 calc PR A 2
C44C C 0.3328(3) 0.0704(5) 0.6745(8) 0.0374(19) Uani 0.441(3) 1 d PDU A 2
H44C H 0.3737 0.0762 0.6390 0.045 Uiso 0.441(3) 1 calc PR A 2
C45C C 0.3224(3) 0.1260(5) 0.7769(8) 0.0349(16) Uani 0.441(3) 1 d PDU A 2
C46C C 0.3712(4) 0.1908(5) 0.8303(10) 0.0468(19) Uani 0.441(3) 1 d PDU A 2
H46C H 0.4118 0.1990 0.7948 0.056 Uiso 0.441(3) 1 calc PR A 2
C47C C 0.3600(4) 0.2412(5) 0.9320(8) 0.0482(19) Uani 0.441(3) 1 d PDU A 2
H47C H 0.3924 0.2855 0.9653 0.058 Uiso 0.441(3) 1 calc PR A 2
C48C C 0.3017(4) 0.2291(4) 0.9887(7) 0.0456(19) Uani 0.441(3) 1 d PDU A 2
H48C H 0.2958 0.2634 1.0624 0.055 Uiso 0.441(3) 1 calc PR A 2
C49C C 0.2529(3) 0.1678(4) 0.9382(6) 0.0357(17) Uani 0.441(3) 1 d PDU A 2
H49C H 0.2123 0.1615 0.9745 0.043 Uiso 0.441(3) 1 calc PR A 2
C50C C 0.2628(3) 0.1139(4) 0.8326(6) 0.0286(14) Uani 0.441(3) 1 d PDU A 2
C51C C 0.2144(3) 0.0492(5) 0.7786(8) 0.0233(17) Uani 0.441(3) 1 d PDU A 2
H51C H 0.1733 0.0422 0.8133 0.028 Uiso 0.441(3) 1 calc PR A 2
O1W O 0.13616(14) 0.10986(17) 0.2139(3) 0.0410(7) Uani 1 1 d D . .
H1W H 0.1836(6) 0.106(2) 0.231(4) 0.049 Uiso 1 1 d D . .
H2W H 0.1420(18) 0.086(2) 0.296(2) 0.049 Uiso 1 1 d D . .
O2W O 0.2550(4) 0.1585(4) 0.1563(9) 0.089(2) Uani 0.559(3) 1 d PD A 1
H3W H 0.294(3) 0.174(4) 0.128(10) 0.107 Uiso 0.559(3) 1 d PD A 1
H4W H 0.266(4) 0.106(2) 0.128(11) 0.107 Uiso 0.559(3) 1 d PD A 1


_geom_special_details            
;
All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell s.u.'s are taken
into account individually in the estimation of s.u.'s in distances, angles
and torsion angles; correlations between s.u.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell s.u.'s is used for estimating s.u.'s 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 O39 1.947(2) 3 ?
Cu1 O9 1.951(2) 3 ?
Cu1 O38 1.955(2) . ?
Cu1 O8 1.964(2) . ?
Cu1 O1W 2.197(2) . ?
Cu1 Cu1 2.6028(7) 3 ?
N1 C2 1.333(4) . ?
N1 C6 1.341(4) . ?
C2 C3 1.374(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.376(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.410(4) . ?
C5 C7 1.495(4) . ?
C6 S10 1.766(3) . ?
C7 O9 1.258(3) . ?
C7 O8 1.262(4) . ?
O9 Cu1 1.951(2) 3 ?
S10 C11 1.818(3) . ?
C11 C12 1.499(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C21 1.363(4) . ?
C12 C13 1.411(4) . ?
C13 C14 1.367(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.407(4) . ?
C14 H14 0.9500 . ?
C15 C20 1.415(4) . ?
C15 C16 1.417(4) . ?
C16 C17 1.357(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.371(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.413(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.414(4) . ?
C21 H21 0.9500 . ?
N31 C32 1.329(4) . ?
N31 C36 1.335(4) . ?
C32 C33 1.374(5) . ?
C32 H32 0.9500 . ?
C33 C34 1.376(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.390(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.409(4) . ?
C35 C37 1.480(4) . ?
C36 S40 1.771(3) . ?
C37 O38 1.259(4) . ?
C37 O39 1.267(4) . ?
O39 Cu1 1.947(2) 3 ?
S40 C41C 1.819(10) . ?
S40 C41B 1.853(6) . ?
C41B C42B 1.499(4) . ?
C41B H41C 0.9900 . ?
C41B H41D 0.9900 . ?
C42B C51B 1.363(4) . ?
C42B C43B 1.411(4) . ?
C43B C44B 1.367(4) . ?
C43B H43B 0.9500 . ?
C44B C45B 1.407(4) . ?
C44B H44B 0.9500 . ?
C45B C50B 1.415(4) . ?
C45B C46B 1.417(4) . ?
C46B C47B 1.357(5) . ?
C46B H46B 0.9500 . ?
C47B C48B 1.398(5) . ?
C47B H47B 0.9500 . ?
C48B C49B 1.371(4) . ?
C48B H48B 0.9500 . ?
C49B C50B 1.413(4) . ?
C49B H49B 0.9500 . ?
C50B C51B 1.414(4) . ?
C51B H51B 0.9500 . ?
C41C C42C 1.499(4) . ?
C41C H41E 0.9900 . ?
C41C H41F 0.9900 . ?
C42C C51C 1.363(4) . ?
C42C C43C 1.410(4) . ?
C43C C44C 1.367(4) . ?
C43C H43C 0.9500 . ?
C44C C45C 1.407(4) . ?
C44C H44C 0.9500 . ?
C45C C50C 1.415(4) . ?
C45C C46C 1.417(4) . ?
C46C C47C 1.357(5) . ?
C46C H46C 0.9500 . ?
C47C C48C 1.398(5) . ?
C47C H47C 0.9500 . ?
C48C C49C 1.371(4) . ?
C48C H48C 0.9500 . ?
C49C C50C 1.413(4) . ?
C49C H49C 0.9500 . ?
C50C C51C 1.414(4) . ?
C51C H51C 0.9500 . ?
O1W H1W 0.903(10) . ?
O1W H2W 0.895(10) . ?
O2W H3W 0.906(10) . ?
O2W H4W 0.912(10) . ?

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
O39 Cu1 O9 90.46(9) 3 3 ?
O39 Cu1 O38 169.23(9) 3 . ?
O9 Cu1 O38 89.79(9) 3 . ?
O39 Cu1 O8 89.04(9) 3 . ?
O9 Cu1 O8 169.31(8) 3 . ?
O38 Cu1 O8 88.72(9) . . ?
O39 Cu1 O1W 104.10(10) 3 . ?
O9 Cu1 O1W 98.88(10) 3 . ?
O38 Cu1 O1W 86.61(10) . . ?
O8 Cu1 O1W 91.61(10) . . ?
O39 Cu1 Cu1 88.34(6) 3 3 ?
O9 Cu1 Cu1 85.23(7) 3 3 ?
O38 Cu1 Cu1 80.94(6) . 3 ?
O8 Cu1 Cu1 84.07(6) . 3 ?
O1W Cu1 Cu1 166.80(7) . 3 ?
C2 N1 C6 118.5(3) . . ?
N1 C2 C3 124.2(3) . . ?
N1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C2 C3 C4 117.2(3) . . ?
C2 C3 H3 121.4 . . ?
C4 C3 H3 121.4 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 C7 118.4(3) . . ?
C6 C5 C7 123.4(3) . . ?
N1 C6 C5 121.3(3) . . ?
N1 C6 S10 116.5(2) . . ?
C5 C6 S10 122.3(2) . . ?
O9 C7 O8 125.4(3) . . ?
O9 C7 C5 117.4(3) . . ?
O8 C7 C5 117.2(3) . . ?
C7 O8 Cu1 122.87(19) . . ?
C7 O9 Cu1 122.16(19) . 3 ?
C6 S10 C11 99.67(14) . . ?
C12 C11 S10 110.2(2) . . ?
C12 C11 H11A 109.6 . . ?
S10 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
S10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C21 C12 C13 118.7(3) . . ?
C21 C12 C11 120.7(3) . . ?
C13 C12 C11 120.4(2) . . ?
C14 C13 C12 120.9(3) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C20 118.6(3) . . ?
C14 C15 C16 122.3(3) . . ?
C20 C15 C16 119.1(3) . . ?
C17 C16 C15 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C19 C18 C17 120.3(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.3(3) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 122.3(3) . . ?
C19 C20 C15 119.0(3) . . ?
C21 C20 C15 118.7(3) . . ?
C12 C21 C20 122.0(3) . . ?
C12 C21 H21 119.0 . . ?
C20 C21 H21 119.0 . . ?
C32 N31 C36 118.1(3) . . ?
N31 C32 C33 124.7(3) . . ?
N31 C32 H32 117.6 . . ?
C33 C32 H32 117.6 . . ?
C32 C33 C34 117.0(3) . . ?
C32 C33 H33 121.5 . . ?
C34 C33 H33 121.5 . . ?
C33 C34 C35 120.8(3) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C34 C35 C36 117.3(3) . . ?
C34 C35 C37 119.7(3) . . ?
C36 C35 C37 123.0(3) . . ?
N31 C36 C35 122.1(3) . . ?
N31 C36 S40 115.7(2) . . ?
C35 C36 S40 122.2(2) . . ?
O38 C37 O39 125.0(3) . . ?
O38 C37 C35 117.4(3) . . ?
O39 C37 C35 117.6(3) . . ?
C37 O38 Cu1 127.2(2) . . ?
C37 O39 Cu1 118.54(19) . 3 ?
C36 S40 C41C 105.3(2) . . ?
C36 S40 C41B 96.55(15) . . ?
C42B C41B S40 104.8(7) . . ?
C42B C41B H41C 110.8 . . ?
S40 C41B H41C 110.8 . . ?
C42B C41B H41D 110.8 . . ?
S40 C41B H41D 110.8 . . ?
H41C C41B H41D 108.9 . . ?
C51B C42B C43B 118.7(3) . . ?
C51B C42B C41B 120.8(3) . . ?
C43B C42B C41B 120.5(3) . . ?
C44B C43B C42B 120.9(3) . . ?
C44B C43B H43B 119.6 . . ?
C42B C43B H43B 119.6 . . ?
C43B C44B C45B 121.1(3) . . ?
C43B C44B H44B 119.4 . . ?
C45B C44B H44B 119.4 . . ?
C44B C45B C50B 118.5(3) . . ?
C44B C45B C46B 122.3(3) . . ?
C50B C45B C46B 119.1(3) . . ?
C47B C46B C45B 120.2(3) . . ?
C47B C46B H46B 119.9 . . ?
C45B C46B H46B 119.9 . . ?
C46B C47B C48B 120.9(3) . . ?
C46B C47B H47B 119.5 . . ?
C48B C47B H47B 119.5 . . ?
C49B C48B C47B 120.4(3) . . ?
C49B C48B H48B 119.8 . . ?
C47B C48B H48B 119.8 . . ?
C48B C49B C50B 120.3(3) . . ?
C48B C49B H49B 119.9 . . ?
C50B C49B H49B 119.9 . . ?
C49B C50B C51B 122.3(3) . . ?
C49B C50B C45B 119.0(3) . . ?
C51B C50B C45B 118.7(3) . . ?
C42B C51B C50B 122.0(3) . . ?
C42B C51B H51B 119.0 . . ?
C50B C51B H51B 119.0 . . ?
C42C C41C S40 110.7(10) . . ?
C42C C41C H41E 109.5 . . ?
S40 C41C H41E 109.5 . . ?
C42C C41C H41F 109.5 . . ?
S40 C41C H41F 109.5 . . ?
H41E C41C H41F 108.1 . . ?
C51C C42C C43C 118.7(3) . . ?
C51C C42C C41C 120.7(3) . . ?
C43C C42C C41C 120.6(3) . . ?
C44C C43C C42C 120.9(3) . . ?
C44C C43C H43C 119.6 . . ?
C42C C43C H43C 119.6 . . ?
C43C C44C C45C 121.1(3) . . ?
C43C C44C H44C 119.5 . . ?
C45C C44C H44C 119.5 . . ?
C44C C45C C50C 118.5(3) . . ?
C44C C45C C46C 122.4(3) . . ?
C50C C45C C46C 119.1(3) . . ?
C47C C46C C45C 120.3(3) . . ?
C47C C46C H46C 119.9 . . ?
C45C C46C H46C 119.9 . . ?
C46C C47C C48C 121.0(3) . . ?
C46C C47C H47C 119.5 . . ?
C48C C47C H47C 119.5 . . ?
C49C C48C C47C 120.3(3) . . ?
C49C C48C H48C 119.9 . . ?
C47C C48C H48C 119.9 . . ?
C48C C49C C50C 120.3(3) . . ?
C48C C49C H49C 119.8 . . ?
C50C C49C H49C 119.8 . . ?
C49C C50C C51C 122.3(3) . . ?
C49C C50C C45C 119.0(3) . . ?
C51C C50C C45C 118.7(3) . . ?
C42C C51C C50C 122.0(3) . . ?
C42C C51C H51C 119.0 . . ?
C50C C51C H51C 119.0 . . ?
Cu1 O1W H1W 133(3) . . ?
Cu1 O1W H2W 112(2) . . ?
H1W O1W H2W 83(3) . . ?
H3W O2W H4W 82.7(12) . . ?

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
C6 N1 C2 C3 -1.2(5) . . . . ?
N1 C2 C3 C4 1.2(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.6(4) . . . . ?
C3 C4 C5 C7 174.9(3) . . . . ?
C2 N1 C6 C5 0.2(4) . . . . ?
C2 N1 C6 S10 -179.4(2) . . . . ?
C4 C5 C6 N1 0.6(4) . . . . ?
C7 C5 C6 N1 -174.6(3) . . . . ?
C4 C5 C6 S10 -179.8(2) . . . . ?
C7 C5 C6 S10 5.0(4) . . . . ?
C4 C5 C7 O9 0.6(4) . . . . ?
C6 C5 C7 O9 175.8(3) . . . . ?
C4 C5 C7 O8 -178.3(3) . . . . ?
C6 C5 C7 O8 -3.1(4) . . . . ?
O9 C7 O8 Cu1 -6.6(4) . . . . ?
C5 C7 O8 Cu1 172.14(18) . . . . ?
O39 Cu1 O8 C7 -85.7(2) 3 . . . ?
O9 Cu1 O8 C7 1.7(6) 3 . . . ?
O38 Cu1 O8 C7 83.8(2) . . . . ?
O1W Cu1 O8 C7 170.3(2) . . . . ?
Cu1 Cu1 O8 C7 2.8(2) 3 . . . ?
O8 C7 O9 Cu1 6.8(4) . . . 3 ?
C5 C7 O9 Cu1 -171.89(18) . . . 3 ?
N1 C6 S10 C11 6.0(3) . . . . ?
C5 C6 S10 C11 -173.6(2) . . . . ?
C6 S10 C11 C12 -173.3(2) . . . . ?
S10 C11 C12 C21 -129.0(3) . . . . ?
S10 C11 C12 C13 55.6(4) . . . . ?
C21 C12 C13 C14 -1.9(5) . . . . ?
C11 C12 C13 C14 173.7(3) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C20 1.5(5) . . . . ?
C13 C14 C15 C16 -176.7(4) . . . . ?
C14 C15 C16 C17 177.4(4) . . . . ?
C20 C15 C16 C17 -0.9(6) . . . . ?
C15 C16 C17 C18 2.1(7) . . . . ?
C16 C17 C18 C19 -1.5(8) . . . . ?
C17 C18 C19 C20 -0.3(7) . . . . ?
C18 C19 C20 C21 -177.2(4) . . . . ?
C18 C19 C20 C15 1.5(6) . . . . ?
C14 C15 C20 C19 -179.2(3) . . . . ?
C16 C15 C20 C19 -0.9(5) . . . . ?
C14 C15 C20 C21 -0.5(5) . . . . ?
C16 C15 C20 C21 177.8(3) . . . . ?
C13 C12 C21 C20 3.0(5) . . . . ?
C11 C12 C21 C20 -172.5(3) . . . . ?
C19 C20 C21 C12 176.9(3) . . . . ?
C15 C20 C21 C12 -1.8(5) . . . . ?
C36 N31 C32 C33 2.1(5) . . . . ?
N31 C32 C33 C34 -1.5(5) . . . . ?
C32 C33 C34 C35 -0.7(4) . . . . ?
C33 C34 C35 C36 2.1(4) . . . . ?
C33 C34 C35 C37 -178.3(3) . . . . ?
C32 N31 C36 C35 -0.4(4) . . . . ?
C32 N31 C36 S40 -179.2(2) . . . . ?
C34 C35 C36 N31 -1.6(4) . . . . ?
C37 C35 C36 N31 178.9(3) . . . . ?
C34 C35 C36 S40 177.0(2) . . . . ?
C37 C35 C36 S40 -2.5(4) . . . . ?
C34 C35 C37 O38 170.8(3) . . . . ?
C36 C35 C37 O38 -9.7(4) . . . . ?
C34 C35 C37 O39 -8.6(4) . . . . ?
C36 C35 C37 O39 170.9(3) . . . . ?
O39 C37 O38 Cu1 -1.1(4) . . . . ?
C35 C37 O38 Cu1 179.61(19) . . . . ?
O39 Cu1 O38 C37 -6.6(7) 3 . . . ?
O9 Cu1 O38 C37 84.7(3) 3 . . . ?
O8 Cu1 O38 C37 -84.7(3) . . . . ?
O1W Cu1 O38 C37 -176.4(3) . . . . ?
Cu1 Cu1 O38 C37 -0.5(2) 3 . . . ?
O38 C37 O39 Cu1 2.5(4) . . . 3 ?
C35 C37 O39 Cu1 -178.18(19) . . . 3 ?
N31 C36 S40 C41C 23.0(3) . . . . ?
C35 C36 S40 C41C -155.7(3) . . . . ?
N31 C36 S40 C41B 4.6(3) . . . . ?
C35 C36 S40 C41B -174.1(3) . . . . ?
C36 S40 C41B C42B 174.7(3) . . . . ?
C41C S40 C41B C42B 57.3(6) . . . . ?
S40 C41B C42B C51B 105.7(13) . . . . ?
S40 C41B C42B C43B -77.0(12) . . . . ?
C51B C42B C43B C44B -3.6(18) . . . . ?
C41B C42B C43B C44B 179.1(9) . . . . ?
C42B C43B C44B C45B 0.6(12) . . . . ?
C43B C44B C45B C50B 1.6(10) . . . . ?
C43B C44B C45B C46B -177.4(6) . . . . ?
C44B C45B C46B C47B 177.3(6) . . . . ?
C50B C45B C46B C47B -1.6(10) . . . . ?
C45B C46B C47B C48B 3.5(11) . . . . ?
C46B C47B C48B C49B -2.8(13) . . . . ?
C47B C48B C49B C50B 0.2(13) . . . . ?
C48B C49B C50B C51B -177.5(8) . . . . ?
C48B C49B C50B C45B 1.6(11) . . . . ?
C44B C45B C50B C49B -179.9(6) . . . . ?
C46B C45B C50B C49B -0.9(10) . . . . ?
C44B C45B C50B C51B -0.7(10) . . . . ?
C46B C45B C50B C51B 178.2(7) . . . . ?
C43B C42B C51B C50B 4.5(19) . . . . ?
C41B C42B C51B C50B -178.2(9) . . . . ?
C49B C50B C51B C42B 176.8(11) . . . . ?
C45B C50B C51B C42B -2.4(15) . . . . ?
C36 S40 C41C C42C -156.0(3) . . . . ?
C41B S40 C41C C42C -89.9(6) . . . . ?
S40 C41C C42C C51C 93.0(18) . . . . ?
S40 C41C C42C C43C -86.0(18) . . . . ?
C51C C42C C43C C44C 1(3) . . . . ?
C41C C42C C43C C44C -179.8(13) . . . . ?
C42C C43C C44C C45C -1.9(18) . . . . ?
C43C C44C C45C C50C 2.8(15) . . . . ?
C43C C44C C45C C46C 179.8(10) . . . . ?
C44C C45C C46C C47C -178.0(11) . . . . ?
C50C C45C C46C C47C -1.0(17) . . . . ?
C45C C46C C47C C48C 1.7(17) . . . . ?
C46C C47C C48C C49C -2.7(16) . . . . ?
C47C C48C C49C C50C 2.8(13) . . . . ?
C48C C49C C50C C51C 179.2(9) . . . . ?
C48C C49C C50C C45C -2.0(13) . . . . ?
C44C C45C C50C C49C 178.2(9) . . . . ?
C46C C45C C50C C49C 1.1(14) . . . . ?
C44C C45C C50C C51C -3.0(14) . . . . ?
C46C C45C C50C C51C 179.9(10) . . . . ?
C43C C42C C51C C50C -1(3) . . . . ?
C41C C42C C51C C50C 179.5(12) . . . . ?
C49C C50C C51C C42C -178.8(14) . . . . ?
C45C C50C C51C C42C 2.4(18) . . . . ?
# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
# !@#$%^&*()_+{}:"~<>?|\-=[];'`,./

# END of CIF


####################################################################### 
# 
# 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_safinddds99
_database_code_depnum_ccdc_archive 'CCDC 959012'
_audit_update_record             
;
2013-09-03 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H7 N O3'
_chemical_formula_sum            'C7 H7 N O3'
_chemical_formula_weight         153.14

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   7.39817(15)
_cell_length_b                   13.0179(2)
_cell_length_c                   14.3767(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1384.60(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10493
_cell_measurement_theta_min      3.0904
_cell_measurement_theta_max      25.2933

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_min  0.91803
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '180 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16333
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_sigmaI/netI    0.0091
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.47
_diffrn_reflns_theta_max         25.35
_reflns_number_total             1242
_reflns_number_gt                1169
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0579P)²+0.3611P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1242
_refine_ls_number_parameters     107
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1108
_refine_ls_wR_factor_gt          0.1093
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1956(2) 0.90668(10) 0.23847(9) 0.0430(4) Uani 1 1 d . . .
H1 H 0.2207 0.9389 0.1822 0.052 Uiso 1 1 calc R . .
C2 C 0.23634(19) 0.95702(10) 0.32100(10) 0.0445(4) Uani 1 1 d . . .
H2 H 0.2866 1.0225 0.3199 0.053 Uiso 1 1 calc R . .
C3 C 0.20177(18) 0.90938(10) 0.40376(9) 0.0410(4) Uani 1 1 d . . .
N4 N 0.12441(15) 0.81473(8) 0.40272(8) 0.0400(3) Uani 1 1 d . . .
H4 H 0.109(2) 0.7836(11) 0.4574(13) 0.048 Uiso 1 1 d . . .
C5 C 0.07888(17) 0.76149(10) 0.32427(8) 0.0369(3) Uani 1 1 d . . .
C6 C 0.11939(17) 0.81089(10) 0.23789(9) 0.0373(3) Uani 1 1 d . . .
C7 C 0.07691(19) 0.75812(11) 0.14978(9) 0.0444(4) Uani 1 1 d . . .
O8 O 0.11154(17) 0.79505(8) 0.07384(7) 0.0605(4) Uani 1 1 d . . .
O9 O -0.00328(16) 0.66813(8) 0.15692(8) 0.0580(4) Uani 1 1 d . . .
H9 H -0.013(3) 0.6533(14) 0.2235(14) 0.070 Uiso 1 1 d . . .
C10 C 0.2458(2) 0.95440(12) 0.49639(10) 0.0565(4) Uani 1 1 d . . .
H10A H 0.1414 0.9506 0.5360 0.085 Uiso 1 1 calc R . .
H10B H 0.2807 1.0249 0.4888 0.085 Uiso 1 1 calc R . .
H10C H 0.3435 0.9167 0.5241 0.085 Uiso 1 1 calc R . .
O11 O 0.00596(15) 0.67456(7) 0.33145(7) 0.0490(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3685(19) . ?
C1 C2 1.3885(19) . ?
C1 H1 0.9300 . ?
C2 C3 1.3659(19) . ?
C2 H2 0.9300 . ?
C3 N4 1.3587(18) . ?
C3 C10 1.4909(19) . ?
N4 C5 1.3659(16) . ?
N4 H4 0.893(18) . ?
C5 O11 1.2580(16) . ?
C5 C6 1.4302(17) . ?
C6 C7 1.4749(18) . ?
C7 O8 1.2201(17) . ?
C7 O9 1.3172(18) . ?
O9 H9 0.98(2) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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 C1 C2 121.65(12) . . ?
C6 C1 H1 119.2 . . ?
C2 C1 H1 119.2 . . ?
C3 C2 C1 119.30(13) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
N4 C3 C2 118.75(12) . . ?
N4 C3 C10 117.28(12) . . ?
C2 C3 C10 123.97(13) . . ?
C3 N4 C5 124.97(11) . . ?
C3 N4 H4 117.2(10) . . ?
C5 N4 H4 117.7(10) . . ?
O11 C5 N4 119.64(11) . . ?
O11 C5 C6 124.44(11) . . ?
N4 C5 C6 115.92(12) . . ?
C1 C6 C5 119.38(12) . . ?
C1 C6 C7 121.16(12) . . ?
C5 C6 C7 119.45(12) . . ?
O8 C7 O9 120.99(12) . . ?
O8 C7 C6 122.70(13) . . ?
O9 C7 C6 116.31(12) . . ?
C7 O9 H9 106.6(11) . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C6 C1 C2 C3 0.8(2) . . . . ?
C1 C2 C3 N4 -1.5(2) . . . . ?
C1 C2 C3 C10 177.78(13) . . . . ?
C2 C3 N4 C5 0.7(2) . . . . ?
C10 C3 N4 C5 -178.61(12) . . . . ?
C3 N4 C5 O11 -179.27(12) . . . . ?
C3 N4 C5 C6 0.7(2) . . . . ?
C2 C1 C6 C5 0.6(2) . . . . ?
C2 C1 C6 C7 -179.92(13) . . . . ?
O11 C5 C6 C1 178.64(12) . . . . ?
N4 C5 C6 C1 -1.34(19) . . . . ?
O11 C5 C6 C7 -0.8(2) . . . . ?
N4 C5 C6 C7 179.17(11) . . . . ?
C1 C6 C7 O8 2.1(2) . . . . ?
C5 C6 C7 O8 -178.39(13) . . . . ?
C1 C6 C7 O9 -177.17(12) . . . . ?
C5 C6 C7 O9 2.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.030
####################################################################### 
# 
# 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_C1a
_database_code_depnum_ccdc_archive 'CCDC 1059621'
_audit_update_record             
;
2016-10-23 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C14 H15 Cu N2 O11 S, 2(H2 O)'
_chemical_formula_sum            'C14 H20 Cu N2 O13 S'
_chemical_compound_source        Synthetic
_exptl_crystal_recrystallization_method methanol
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            green

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         519.92

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.7731(5)
_cell_length_b                   13.7449(7)
_cell_length_c                   16.6071(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.648(2)
_cell_angle_gamma                90
_cell_volume                     1998.52(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    207
_cell_measurement_theta_min      4.45
_cell_measurement_theta_max      25.84
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.728
_exptl_crystal_F_000             1068
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    1.270
_shelx_estimated_absorpt_T_min   0.804
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5685
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Bruker AXS Inc.)'

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker D8 Quest CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40334
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         27.175
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             8790
_reflns_number_gt                8279
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.910
_reflns_Friedel_fraction_max     0.985
_reflns_Friedel_fraction_full    0.987

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

_computing_data_collection       'Bruker Smart'
_computing_cell_refinement       'Bruker Smart'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    
'OLEX2 (Dolomanov et al 2009); Mercury (Macrae et al 2008)'

_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)+(0.0327P)²+0.9585P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 3765 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.034(3)
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   P21
_symmetry_int_tables_number      4
_chemical_absolute_configuration .
_refine_ls_number_reflns         8790
_refine_ls_number_parameters     618
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0255
_refine_ls_wR_factor_ref         0.0664
_refine_ls_wR_factor_gt          0.0654
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.064
_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
CuA Cu 0.42907(4) 0.33185(3) 0.29271(2) 0.01123(10) Uani 1 1 d . . . . .
O1A O 0.6478(3) 0.3452(2) 0.28215(14) 0.0137(5) Uani 1 1 d . . . . .
C2A C 0.7158(3) 0.3294(3) 0.21961(18) 0.0126(6) Uani 1 1 d . . . . .
O3A O 0.8605(3) 0.3186(2) 0.22020(15) 0.0195(6) Uani 1 1 d . . . . .
H3A H 0.902(5) 0.309(3) 0.267(3) 0.023 Uiso 1 1 d . U . . .
C4A C 0.6348(4) 0.3242(3) 0.1379(2) 0.0130(6) Uani 1 1 d . . . . .
C5A C 0.4774(4) 0.3499(2) 0.1263(2) 0.0119(7) Uani 1 1 d . . . . .
N6A N 0.4186(3) 0.3512(2) 0.04779(17) 0.0141(6) Uani 1 1 d D . . . .
H6A H 0.3213(19) 0.363(3) 0.040(2) 0.017 Uiso 1 1 d D U . . .
C7A C 0.4971(4) 0.3277(3) -0.01742(18) 0.0168(7) Uani 1 1 d . . . . .
C8A C 0.6459(4) 0.2988(3) -0.0059(2) 0.0220(9) Uani 1 1 d . . . . .
H8A H 0.7015 0.2791 -0.0504 0.026 Uiso 1 1 calc R U . . .
C9A C 0.7150(4) 0.2987(3) 0.0720(2) 0.0185(8) Uani 1 1 d . . . . .
H9A H 0.8194 0.2807 0.0801 0.022 Uiso 1 1 calc R U . . .
O10A O 0.3877(3) 0.37238(18) 0.18027(14) 0.0132(5) Uani 1 1 d . . . . .
C11A C 0.4119(4) 0.3330(4) -0.0989(2) 0.0223(7) Uani 1 1 d . . . . .
H11A H 0.3227 0.2901 -0.0997 0.027 Uiso 1 1 calc R U . . .
H11B H 0.4792 0.3124 -0.1406 0.027 Uiso 1 1 calc R U . . .
H11C H 0.3782 0.4001 -0.1095 0.027 Uiso 1 1 calc R U . . .
O12A O 0.2102(3) 0.30978(18) 0.29797(13) 0.0138(5) Uani 1 1 d . . . . .
C13A C 0.1333(4) 0.3119(2) 0.35984(19) 0.0122(7) Uani 1 1 d . . . . .
O14A O -0.0118(3) 0.3098(2) 0.35493(14) 0.0199(6) Uani 1 1 d . . . . .
C15A C 0.2053(4) 0.3161(3) 0.44342(19) 0.0130(7) Uani 1 1 d . . . . .
C16A C 0.3678(4) 0.3196(3) 0.45851(19) 0.0118(7) Uani 1 1 d . . . . .
N17A N 0.4198(3) 0.3292(3) 0.53765(16) 0.0139(5) Uani 1 1 d D . . . .
H17A H 0.5192(17) 0.327(3) 0.548(2) 0.017 Uiso 1 1 d D U . . .
C18A C 0.3294(4) 0.3343(3) 0.60117(19) 0.0166(7) Uani 1 1 d . . . . .
C19A C 0.1735(4) 0.3272(3) 0.5864(2) 0.0207(7) Uani 1 1 d . . . . .
H19A H 0.1081 0.3280 0.6298 0.025 Uiso 1 1 calc R U . . .
C20A C 0.1134(4) 0.3190(3) 0.5079(2) 0.0166(7) Uani 1 1 d . . . . .
H20A H 0.0058 0.3151 0.4979 0.020 Uiso 1 1 calc R U . . .
O21A O 0.4684(3) 0.31312(19) 0.40705(13) 0.0144(5) Uani 1 1 d . . . . .
C22A C 0.4068(5) 0.3502(3) 0.6832(2) 0.0219(8) Uani 1 1 d . . . . .
H22A H 0.4792 0.2972 0.6956 0.026 Uiso 1 1 calc R U . . .
H22B H 0.3302 0.3515 0.7236 0.026 Uiso 1 1 calc R U . . .
H22C H 0.4618 0.4123 0.6840 0.026 Uiso 1 1 calc R U . . .
O23A O 0.4589(3) 0.16887(18) 0.26423(15) 0.0146(5) Uani 1 1 d D . . . .
H23A H 0.384(3) 0.138(3) 0.247(2) 0.018 Uiso 1 1 d D U . . .
H23B H 0.527(4) 0.143(3) 0.240(2) 0.018 Uiso 1 1 d D U . . .
CuB Cu 0.86765(4) 0.57270(3) 0.88102(2) 0.01087(9) Uani 1 1 d . . . . .
O1B O 1.0864(3) 0.5671(2) 0.87134(14) 0.0155(5) Uani 1 1 d . . . . .
C2B C 1.1599(3) 0.5760(3) 0.80956(19) 0.0112(6) Uani 1 1 d . . . . .
O3B O 1.3052(3) 0.5813(2) 0.81460(14) 0.0154(5) Uani 1 1 d . . . . .
C4B C 1.0844(4) 0.5765(3) 0.7266(2) 0.0119(6) Uani 1 1 d . . . . .
C5B C 0.9226(4) 0.5726(3) 0.71266(18) 0.0114(6) Uani 1 1 d . . . . .
N6B N 0.8684(3) 0.5654(2) 0.63403(16) 0.0126(6) Uani 1 1 d D . . . .
H6B H 0.7708(19) 0.556(3) 0.624(3) 0.015 Uiso 1 1 d D U . . .
C7B C 0.9549(4) 0.5645(3) 0.56878(19) 0.0157(7) Uani 1 1 d . . . . .
C8B C 1.1101(4) 0.5717(4) 0.5818(2) 0.0210(8) Uani 1 1 d . . . . .
H8B H 1.1737 0.5729 0.5376 0.025 Uiso 1 1 calc R U . . .
C9B C 1.1733(4) 0.5772(3) 0.6604(2) 0.0197(7) Uani 1 1 d . . . . .
H9B H 1.2811 0.5817 0.6692 0.024 Uiso 1 1 calc R U . . .
O10B O 0.8232(2) 0.5754(2) 0.76532(13) 0.0136(4) Uani 1 1 d . . . . .
C11B C 0.8728(4) 0.5516(3) 0.4880(2) 0.0223(9) Uani 1 1 d . . . . .
H11D H 0.8240 0.4874 0.4852 0.027 Uiso 1 1 calc R U . . .
H11E H 0.9457 0.5566 0.4459 0.027 Uiso 1 1 calc R U . . .
H11F H 0.7947 0.6022 0.4798 0.027 Uiso 1 1 calc R U . . .
O12B O 0.6467(2) 0.5684(2) 0.89201(13) 0.0128(5) Uani 1 1 d . . . . .
C13B C 0.5747(3) 0.5706(3) 0.95428(19) 0.0113(6) Uani 1 1 d . . . . .
O14B O 0.4280(3) 0.5720(2) 0.95189(14) 0.0166(5) Uani 1 1 d . . . . .
H14B H 0.397(8) 0.560(6) 0.901(4) 0.08(2) Uiso 1 1 d . . . . .
C15B C 0.6496(4) 0.5709(3) 1.03638(19) 0.0122(6) Uani 1 1 d . . . . .
C16B C 0.8109(4) 0.5608(3) 1.04972(19) 0.0106(6) Uani 1 1 d . . . . .
N17B N 0.8673(3) 0.5563(2) 1.12811(17) 0.0136(6) Uani 1 1 d D . . . .
H17B H 0.9671(18) 0.555(3) 1.139(2) 0.016 Uiso 1 1 d D U . . .
C18B C 0.7831(4) 0.5654(3) 1.1938(2) 0.0158(7) Uani 1 1 d . . . . .
C19B C 0.6273(4) 0.5765(3) 1.1816(2) 0.0184(7) Uani 1 1 d . . . . .
H19B H 0.5655 0.5830 1.2262 0.022 Uiso 1 1 calc R U . . .
C20B C 0.5615(4) 0.5781(3) 1.1033(2) 0.0157(7) Uani 1 1 d . . . . .
H20B H 0.4538 0.5843 1.0950 0.019 Uiso 1 1 calc R U . . .
O21B O 0.9087(3) 0.55477(18) 0.99606(14) 0.0137(5) Uani 1 1 d . . . . .
C22B C 0.8664(4) 0.5625(4) 1.2747(2) 0.0235(9) Uani 1 1 d . . . . .
H22D H 0.9500 0.5152 1.2742 0.028 Uiso 1 1 calc R U . . .
H22E H 0.7959 0.5433 1.3153 0.028 Uiso 1 1 calc R U . . .
H22F H 0.9082 0.6271 1.2880 0.028 Uiso 1 1 calc R U . . .
O23B O 0.8703(3) 0.7377(2) 0.87667(15) 0.0205(6) Uani 1 1 d D . . . .
H23C H 0.903(5) 0.782(2) 0.908(2) 0.025 Uiso 1 1 d D U . . .
H23D H 0.858(5) 0.766(3) 0.8323(15) 0.025 Uiso 1 1 d D U . . .
S1 S 0.35806(9) 0.57693(8) 0.37922(5) 0.01346(16) Uani 1 1 d . . . . .
O111 O 0.3468(4) 0.5084(2) 0.31364(17) 0.0304(7) Uani 1 1 d . . . . .
O121 O 0.2167(3) 0.6298(2) 0.38219(19) 0.0297(7) Uani 1 1 d . . . . .
O131 O 0.3844(4) 0.5246(2) 0.45423(16) 0.0265(6) Uani 1 1 d . . . . .
O141 O 0.4818(3) 0.6419(2) 0.3696(2) 0.0330(7) Uani 1 1 d . . . . .
S2 S 0.90166(10) 0.31281(6) 0.80804(5) 0.01706(18) Uani 1 1 d . . . . .
O211 O 0.8780(5) 0.3846(2) 0.8685(2) 0.0497(11) Uani 1 1 d . . . . .
O221 O 0.7738(4) 0.2475(2) 0.8009(2) 0.0346(7) Uani 1 1 d . . . . .
O231 O 0.9197(4) 0.3600(2) 0.73271(17) 0.0317(7) Uani 1 1 d . . . . .
O241 O 1.0353(4) 0.2591(3) 0.8322(3) 0.0641(13) Uani 1 1 d . . . . .
O100 O 0.5588(3) 0.5632(3) 0.59583(17) 0.0278(6) Uani 1 1 d D . . . .
H101 H 0.506(5) 0.567(4) 0.5527(16) 0.033 Uiso 1 1 d D U . . .
H102 H 0.524(5) 0.606(3) 0.624(3) 0.033 Uiso 1 1 d D U . . .
O200 O 0.2600(3) 0.8331(3) 0.42036(17) 0.0251(6) Uani 1 1 d D . . . .
H201 H 0.246(5) 0.7741(13) 0.414(3) 0.030 Uiso 1 1 d D U . . .
H202 H 0.230(5) 0.850(4) 0.3743(14) 0.030 Uiso 1 1 d D U . . .
O300 O 0.1063(3) 0.3897(2) 0.00872(17) 0.0263(6) Uani 1 1 d D . . . .
H301 H 0.059(5) 0.380(4) -0.0352(16) 0.032 Uiso 1 1 d D U . . .
H302 H 0.075(5) 0.4466(16) 0.014(3) 0.032 Uiso 1 1 d D U . . .
O400 O 1.1831(3) 0.5441(2) 1.15054(17) 0.0229(6) Uani 1 1 d D . . . .
H401 H 1.226(5) 0.498(2) 1.175(3) 0.027 Uiso 1 1 d D U . . .
H402 H 1.205(5) 0.593(2) 1.178(2) 0.027 Uiso 1 1 d D 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
CuA O21A 1.925(2) . ?
CuA O1A 1.947(2) . ?
CuA O12A 1.951(2) . ?
CuA O10A 1.960(2) . ?
CuA O23A 2.308(3) . ?
O1A C2A 1.249(4) . ?
C2A O3A 1.278(4) . ?
C2A C4A 1.493(4) . ?
O3A H3A 0.85(5) . ?
C4A C9A 1.383(5) . ?
C4A C5A 1.426(4) . ?
C5A O10A 1.269(4) . ?
C5A N6A 1.371(4) . ?
N6A C7A 1.359(4) . ?
N6A H6A 0.871(14) . ?
C7A C8A 1.366(5) . ?
C7A C11A 1.506(4) . ?
C8A C9A 1.394(5) . ?
C8A H8A 0.9500 . ?
C9A H9A 0.9500 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
O12A C13A 1.265(4) . ?
C13A O14A 1.271(4) . ?
C13A C15A 1.489(4) . ?
C15A C20A 1.382(4) . ?
C15A C16A 1.432(4) . ?
C16A O21A 1.270(4) . ?
C16A N17A 1.370(4) . ?
N17A C18A 1.362(4) . ?
N17A H17A 0.878(14) . ?
C18A C19A 1.377(5) . ?
C18A C22A 1.499(5) . ?
C19A C20A 1.379(5) . ?
C19A H19A 0.9500 . ?
C20A H20A 0.9500 . ?
C22A H22A 0.9800 . ?
C22A H22B 0.9800 . ?
C22A H22C 0.9800 . ?
O23A H23A 0.821(14) . ?
O23A H23B 0.822(14) . ?
CuB O10B 1.937(2) . ?
CuB O21B 1.937(2) . ?
CuB O1B 1.937(2) . ?
CuB O12B 1.960(2) . ?
CuB O23B 2.269(3) . ?
O1B C2B 1.252(4) . ?
C2B O3B 1.274(4) . ?
C2B C4B 1.490(4) . ?
C4B C9B 1.388(4) . ?
C4B C5B 1.425(4) . ?
C5B O10B 1.274(4) . ?
C5B N6B 1.364(4) . ?
N6B C7B 1.362(4) . ?
N6B H6B 0.871(14) . ?
C7B C8B 1.369(5) . ?
C7B C11B 1.492(5) . ?
C8B C9B 1.387(5) . ?
C8B H8B 0.9500 . ?
C9B H9B 0.9500 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
O12B C13B 1.246(4) . ?
C13B O14B 1.286(4) . ?
C13B C15B 1.475(4) . ?
O14B H14B 0.88(7) . ?
C15B C20B 1.396(4) . ?
C15B C16B 1.425(4) . ?
C16B O21B 1.279(4) . ?
C16B N17B 1.364(4) . ?
N17B C18B 1.362(4) . ?
N17B H17B 0.883(14) . ?
C18B C19B 1.378(5) . ?
C18B C22B 1.489(5) . ?
C19B C20B 1.389(5) . ?
C19B H19B 0.9500 . ?
C20B H20B 0.9500 . ?
C22B H22D 0.9800 . ?
C22B H22E 0.9800 . ?
C22B H22F 0.9800 . ?
O23B H23C 0.833(14) . ?
O23B H23D 0.833(14) . ?
S1 O141 1.422(3) . ?
S1 O111 1.439(3) . ?
S1 O121 1.441(3) . ?
S1 O131 1.445(3) . ?
S2 O241 1.421(4) . ?
S2 O231 1.427(3) . ?
S2 O211 1.432(3) . ?
S2 O221 1.436(3) . ?
O100 H101 0.831(14) . ?
O100 H102 0.824(14) . ?
O200 H201 0.826(14) . ?
O200 H202 0.827(14) . ?
O300 H301 0.827(14) . ?
O300 H302 0.832(14) . ?
O400 H401 0.829(14) . ?
O400 H402 0.827(14) . ?

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
O21A CuA O1A 89.19(10) . . ?
O21A CuA O12A 92.87(9) . . ?
O1A CuA O12A 175.64(11) . . ?
O21A CuA O10A 171.15(11) . . ?
O1A CuA O10A 90.65(10) . . ?
O12A CuA O10A 87.91(10) . . ?
O21A CuA O23A 93.26(10) . . ?
O1A CuA O23A 87.02(10) . . ?
O12A CuA O23A 89.02(9) . . ?
O10A CuA O23A 95.58(10) . . ?
C2A O1A CuA 125.7(2) . . ?
O1A C2A O3A 122.7(3) . . ?
O1A C2A C4A 122.6(3) . . ?
O3A C2A C4A 114.6(3) . . ?
C2A O3A H3A 113(3) . . ?
C9A C4A C5A 119.5(3) . . ?
C9A C4A C2A 119.6(3) . . ?
C5A C4A C2A 120.8(3) . . ?
O10A C5A N6A 117.1(3) . . ?
O10A C5A C4A 127.1(3) . . ?
N6A C5A C4A 115.7(3) . . ?
C7A N6A C5A 125.1(3) . . ?
C7A N6A H6A 118(3) . . ?
C5A N6A H6A 116(3) . . ?
N6A C7A C8A 119.0(3) . . ?
N6A C7A C11A 117.2(3) . . ?
C8A C7A C11A 123.8(3) . . ?
C7A C8A C9A 119.1(3) . . ?
C7A C8A H8A 120.5 . . ?
C9A C8A H8A 120.5 . . ?
C4A C9A C8A 121.4(3) . . ?
C4A C9A H9A 119.3 . . ?
C8A C9A H9A 119.3 . . ?
C5A O10A CuA 121.2(2) . . ?
C7A C11A H11A 109.5 . . ?
C7A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C7A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C13A O12A CuA 127.6(2) . . ?
O12A C13A O14A 122.1(3) . . ?
O12A C13A C15A 122.8(3) . . ?
O14A C13A C15A 115.1(3) . . ?
C20A C15A C16A 119.1(3) . . ?
C20A C15A C13A 119.3(3) . . ?
C16A C15A C13A 121.5(3) . . ?
O21A C16A N17A 116.7(3) . . ?
O21A C16A C15A 127.3(3) . . ?
N17A C16A C15A 116.0(3) . . ?
C18A N17A C16A 125.0(3) . . ?
C18A N17A H17A 118(3) . . ?
C16A N17A H17A 117(3) . . ?
N17A C18A C19A 118.6(3) . . ?
N17A C18A C22A 117.3(3) . . ?
C19A C18A C22A 124.1(3) . . ?
C18A C19A C20A 119.3(3) . . ?
C18A C19A H19A 120.3 . . ?
C20A C19A H19A 120.3 . . ?
C19A C20A C15A 121.9(3) . . ?
C19A C20A H20A 119.1 . . ?
C15A C20A H20A 119.1 . . ?
C16A O21A CuA 124.5(2) . . ?
C18A C22A H22A 109.5 . . ?
C18A C22A H22B 109.5 . . ?
H22A C22A H22B 109.5 . . ?
C18A C22A H22C 109.5 . . ?
H22A C22A H22C 109.5 . . ?
H22B C22A H22C 109.5 . . ?
CuA O23A H23A 119(3) . . ?
CuA O23A H23B 128(3) . . ?
H23A O23A H23B 101(4) . . ?
O10B CuB O21B 173.75(12) . . ?
O10B CuB O1B 93.24(9) . . ?
O21B CuB O1B 87.35(10) . . ?
O10B CuB O12B 87.42(9) . . ?
O21B CuB O12B 91.57(9) . . ?
O1B CuB O12B 175.93(14) . . ?
O10B CuB O23B 87.18(11) . . ?
O21B CuB O23B 99.03(10) . . ?
O1B CuB O23B 91.43(11) . . ?
O12B CuB O23B 92.62(11) . . ?
C2B O1B CuB 128.9(2) . . ?
O1B C2B O3B 121.1(3) . . ?
O1B C2B C4B 122.4(3) . . ?
O3B C2B C4B 116.4(3) . . ?
C9B C4B C5B 118.4(3) . . ?
C9B C4B C2B 119.6(3) . . ?
C5B C4B C2B 122.0(3) . . ?
O10B C5B N6B 116.6(3) . . ?
O10B C5B C4B 127.3(3) . . ?
N6B C5B C4B 116.2(3) . . ?
C7B N6B C5B 125.8(3) . . ?
C7B N6B H6B 116(3) . . ?
C5B N6B H6B 118(3) . . ?
N6B C7B C8B 118.2(3) . . ?
N6B C7B C11B 117.1(3) . . ?
C8B C7B C11B 124.7(3) . . ?
C7B C8B C9B 119.1(3) . . ?
C7B C8B H8B 120.5 . . ?
C9B C8B H8B 120.5 . . ?
C8B C9B C4B 122.3(3) . . ?
C8B C9B H9B 118.9 . . ?
C4B C9B H9B 118.9 . . ?
C5B O10B CuB 125.2(2) . . ?
C7B C11B H11D 109.5 . . ?
C7B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C7B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C13B O12B CuB 129.3(2) . . ?
O12B C13B O14B 122.3(3) . . ?
O12B C13B C15B 123.2(3) . . ?
O14B C13B C15B 114.5(3) . . ?
C13B O14B H14B 106(4) . . ?
C20B C15B C16B 118.5(3) . . ?
C20B C15B C13B 119.9(3) . . ?
C16B C15B C13B 121.5(3) . . ?
O21B C16B N17B 116.3(3) . . ?
O21B C16B C15B 127.0(3) . . ?
N17B C16B C15B 116.7(3) . . ?
C18B N17B C16B 125.3(3) . . ?
C18B N17B H17B 115(3) . . ?
C16B N17B H17B 120(3) . . ?
N17B C18B C19B 118.4(3) . . ?
N17B C18B C22B 117.4(3) . . ?
C19B C18B C22B 124.2(3) . . ?
C18B C19B C20B 119.3(3) . . ?
C18B C19B H19B 120.4 . . ?
C20B C19B H19B 120.4 . . ?
C19B C20B C15B 121.7(3) . . ?
C19B C20B H20B 119.1 . . ?
C15B C20B H20B 119.1 . . ?
C16B O21B CuB 126.0(2) . . ?
C18B C22B H22D 109.5 . . ?
C18B C22B H22E 109.5 . . ?
H22D C22B H22E 109.5 . . ?
C18B C22B H22F 109.5 . . ?
H22D C22B H22F 109.5 . . ?
H22E C22B H22F 109.5 . . ?
CuB O23B H23C 135(3) . . ?
CuB O23B H23D 120(3) . . ?
H23C O23B H23D 103(4) . . ?
O141 S1 O111 110.03(19) . . ?
O141 S1 O121 110.6(2) . . ?
O111 S1 O121 109.78(19) . . ?
O141 S1 O131 109.15(19) . . ?
O111 S1 O131 109.03(19) . . ?
O121 S1 O131 108.20(19) . . ?
O241 S2 O231 110.3(3) . . ?
O241 S2 O211 108.3(3) . . ?
O231 S2 O211 109.31(19) . . ?
O241 S2 O221 108.9(2) . . ?
O231 S2 O221 109.98(19) . . ?
O211 S2 O221 109.9(2) . . ?
H101 O100 H102 103(5) . . ?
H201 O200 H202 97(5) . . ?
H301 O300 H302 95(5) . . ?
H401 O400 H402 106(5) . . ?

_refine_diff_density_max         0.605
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1060660'
_audit_update_record             
;
2015-04-20 deposited with the CCDC.
2016-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 Cl Cu2 N3 O12, H2 O'
_chemical_formula_sum            'C14 H20 Cl Cu2 N3 O13'
_chemical_formula_weight         600.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_H-M_alt        'F d d d'
_space_group_name_Hall           '-F 2uv 2vw'

_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+1/4, -y+1/4, z'
'x, -y+1/4, -z+1/4'
'-x+1/4, y, -z+1/4'
'x, y+1/2, z+1/2'
'-x+1/4, -y+3/4, z+1/2'
'x, -y+3/4, -z+3/4'
'-x+1/4, y+1/2, -z+3/4'
'x+1/2, y, z+1/2'
'-x+3/4, -y+1/4, z+1/2'
'x+1/2, -y+1/4, -z+3/4'
'-x+3/4, y, -z+3/4'
'x+1/2, y+1/2, z'
'-x+3/4, -y+3/4, z'
'x+1/2, -y+3/4, -z+1/4'
'-x+3/4, y+1/2, -z+1/4'
'-x, -y, -z'
'x-1/4, y-1/4, -z'
'-x, y-1/4, z-1/4'
'x-1/4, -y, z-1/4'
'-x, -y+1/2, -z+1/2'
'x-1/4, y+1/4, -z+1/2'
'-x, y+1/4, z+1/4'
'x-1/4, -y+1/2, z+1/4'
'-x+1/2, -y, -z+1/2'
'x+1/4, y-1/4, -z+1/2'
'-x+1/2, y-1/4, z+1/4'
'x+1/4, -y, z+1/4'
'-x+1/2, -y+1/2, -z'
'x+1/4, y+1/4, -z'
'-x+1/2, y+1/4, z-1/4'
'x+1/4, -y+1/2, z-1/4'

_cell_length_a                   13.0670(9)
_cell_length_b                   17.8555(12)
_cell_length_c                   36.247(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8457.0(10)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1993
_cell_measurement_theta_min      2.245
_cell_measurement_theta_max      25.79

_exptl_crystal_description       prism
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.888
_exptl_crystal_F_000             4864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    2.212
_shelx_estimated_absorpt_T_min   0.630
_shelx_estimated_absorpt_T_max   0.666
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.454
_exptl_absorpt_correction_T_max  0.666
_exptl_absorpt_process_details   'SADABS-2014/5 (bruker, 2014)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14568
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_theta_min         2.011
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2169
_reflns_number_gt                1569
_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       'BRUKER APEX2'
_computing_cell_refinement       'BRUKER APEX2'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0534P)²+55.4429P] 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_number_reflns         2169
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1202
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.7500 0.0000 0.2500 0.0413(2) Uani 1 2 d S . P . .
Cu2 Cu 0.72966(6) -0.1250 0.3750 0.0535(3) Uani 1 2 d S T P . .
O1W O 0.7677(10) 0.1065(3) 0.2370(2) 0.045(3) Uani 0.65(3) 1 d . . P A 1
O1W' O 0.7107(15) 0.0993(5) 0.2290(3) 0.034(4) Uani 0.35(3) 1 d . . P A 2
H1WB H 0.7496 0.1093 0.2102 0.041 Uiso 1 1 d R U . . .
H1WA H 0.7210 0.1312 0.2485 0.041 Uiso 1 1 d R U . . .
O2W O 0.5612(4) -0.1313(4) 0.38553(15) 0.0508(17) Uani 0.5 1 d . . P . .
H2WB H 0.5010 -0.1250 0.3750 0.061 Uiso 1 2 d R U P . .
H2WA H 0.5522 -0.1736 0.3991 0.061 Uiso 0.5 1 d R U P . .
O1 O 0.7583(2) 0.04194(15) 0.30012(9) 0.0470(7) Uani 1 1 d . . . . .
O2 O 0.7396(3) -0.06048(16) 0.33354(10) 0.0592(9) Uani 1 1 d . . . . .
O3 O 0.7509(2) -0.04297(17) 0.40894(9) 0.0568(8) Uani 1 1 d . . . . .
Cl1 Cl 0.9512(2) 0.00317(16) 0.23675(9) 0.0469(6) Uani 0.5 1 d . . P A 3
N10 N 0.9984(5) 0.0407(3) 0.22443(19) 0.0368(15) Uani 0.5 1 d . . P B 4
O10 O 0.9804(5) 0.0146(3) 0.19423(16) 0.0504(14) Uani 0.5 1 d . . P B 4
O11 O 0.9620(10) 0.0109(5) 0.2538(2) 0.076(3) Uani 0.5 1 d . . P B 4
O12 O 1.0546(5) 0.0958(3) 0.2286(2) 0.0632(18) Uani 0.5 1 d . . P B 4
C1 C 0.7490(3) 0.0102(2) 0.33057(13) 0.0447(10) Uani 1 1 d . . . . .
C2 C 0.7499(3) 0.0577(2) 0.36421(12) 0.0445(10) Uani 1 1 d . . . . .
C3 C 0.7522(3) 0.0262(3) 0.40019(14) 0.0492(11) Uani 1 1 d . . . . .
N1 N 0.7574(2) 0.0750(2) 0.42889(11) 0.0505(9) Uani 1 1 d . . . . .
H1 H 0.7606 0.0562 0.4513 0.061 Uiso 1 1 calc R U . . .
C4 C 0.7579(3) 0.1518(3) 0.42539(15) 0.0548(12) Uani 1 1 d . . . . .
C40 C 0.7644(3) 0.1962(3) 0.46008(15) 0.0691(15) Uani 1 1 d . . . . .
H40A H 0.7620 0.2497 0.4542 0.104 Uiso 1 1 calc R U . . .
H40B H 0.8288 0.1847 0.4727 0.104 Uiso 1 1 calc R U . . .
H40C H 0.7068 0.1833 0.4762 0.104 Uiso 1 1 calc R U . . .
C5 C 0.7524(3) 0.1812(3) 0.39092(14) 0.0510(11) Uani 1 1 d . . . . .
H5 H 0.7504 0.2340 0.3876 0.061 Uiso 1 1 calc R U . . .
C6 C 0.7496(3) 0.1343(2) 0.36064(13) 0.0458(10) Uani 1 1 d . . . . .
H6 H 0.7474 0.1556 0.3366 0.055 Uiso 1 1 calc R U . . .
O3W O 1.0583(11) 0.0959(8) 0.1725(4) 0.058(4) Uiso 0.25 1 d . . P C 3
O3W' O 1.0368(11) 0.1222(9) 0.1783(4) 0.061(4) Uiso 0.25 1 d . . P D 3
H3WA H 1.1333 0.1133 0.1741 0.073 Uiso 0.5 1 d R U P D 3
H3WB H 1.0207 0.0783 0.1946 0.073 Uiso 0.5 1 d R U P D 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 O1 1.968(3) 25_655 ?
Cu1 O1 1.968(3) . ?
Cu1 O1W 1.973(5) . ?
Cu1 O1W 1.973(5) 25_655 ?
Cu1 O1W' 1.996(8) 25_655 ?
Cu1 O1W' 1.996(8) . ?
Cu1 Cl1 2.673(3) . ?
Cu1 Cl1 2.673(3) 25_655 ?
Cu2 O2 1.898(3) . ?
Cu2 O2 1.898(3) 7_545 ?
Cu2 O3 1.933(3) 7_545 ?
Cu2 O3 1.933(3) . ?
Cu2 O2W 2.237(6) 7_545 ?
Cu2 O2W 2.237(6) . ?
O1W H1WB 1.0012 . ?
O1W H1WA 0.8608 . ?
O1W' H1WB 0.8692 . ?
O1W' H1WA 0.9166 . ?
O2W H2WB 0.8814 . ?
O2W H2WA 0.9095 . ?
O1 C1 1.247(5) . ?
O2 C1 1.272(5) . ?
O3 C3 1.276(5) . ?
N10 O10 1.213(9) . ?
N10 O12 1.236(8) . ?
N10 O11 1.281(11) . ?
C1 C2 1.486(6) . ?
C2 C6 1.373(6) . ?
C2 C3 1.421(7) . ?
C3 N1 1.358(6) . ?
N1 C4 1.377(6) . ?
N1 H1 0.8800 . ?
C4 C5 1.358(7) . ?
C4 C40 1.488(7) . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
C5 C6 1.381(6) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
O3W H3WA 1.0287 . ?
O3W H3WB 0.9892 . ?
O3W' H3WA 1.2801 . ?
O3W' H3WB 1.0031 . ?

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 O1 180.00(16) 25_655 . ?
O1 Cu1 O1W 98.8(2) 25_655 . ?
O1 Cu1 O1W 81.2(2) . . ?
O1 Cu1 O1W 81.2(2) 25_655 25_655 ?
O1 Cu1 O1W 98.8(2) . 25_655 ?
O1W Cu1 O1W 180.0(4) . 25_655 ?
O1 Cu1 O1W' 91.6(3) 25_655 25_655 ?
O1 Cu1 O1W' 88.4(3) . 25_655 ?
O1 Cu1 O1W' 88.4(3) 25_655 . ?
O1 Cu1 O1W' 91.6(3) . . ?
O1W' Cu1 O1W' 180.0(5) 25_655 . ?
O1 Cu1 Cl1 84.05(10) 25_655 . ?
O1 Cu1 Cl1 95.95(10) . . ?
O1 Cu1 Cl1 95.95(10) 25_655 25_655 ?
O1 Cu1 Cl1 84.05(10) . 25_655 ?
Cl1 Cu1 Cl1 180.0 . 25_655 ?
O2 Cu2 O2 172.2(2) . 7_545 ?
O2 Cu2 O3 86.92(14) . 7_545 ?
O2 Cu2 O3 91.96(14) 7_545 7_545 ?
O2 Cu2 O3 91.96(14) . . ?
O2 Cu2 O3 86.92(14) 7_545 . ?
O3 Cu2 O3 163.52(19) 7_545 . ?
O2 Cu2 O2W 84.37(15) . 7_545 ?
O2 Cu2 O2W 103.46(16) 7_545 7_545 ?
O3 Cu2 O2W 94.0(2) 7_545 7_545 ?
O3 Cu2 O2W 102.2(2) . 7_545 ?
O2 Cu2 O2W 103.46(16) . . ?
O2 Cu2 O2W 84.37(15) 7_545 . ?
O3 Cu2 O2W 102.2(2) 7_545 . ?
O3 Cu2 O2W 94.0(2) . . ?
O2W Cu2 O2W 20.5(2) 7_545 . ?
Cu1 O1W H1WB 104.5 . . ?
Cu1 O1W H1WA 107.2 . . ?
H1WB O1W H1WA 106.1 . . ?
Cu1 O1W' H1WB 109.3 . . ?
Cu1 O1W' H1WA 102.8 . . ?
H1WB O1W' H1WA 113.1 . . ?
Cu2 O2W H2WB 142.9 . . ?
Cu2 O2W H2WA 105.1 . . ?
H2WB O2W H2WA 103.0 . . ?
C1 O1 Cu1 129.7(3) . . ?
C1 O2 Cu2 132.5(3) . . ?
C3 O3 Cu2 125.3(3) . . ?
O10 N10 O12 122.1(7) . . ?
O10 N10 O11 121.1(8) . . ?
O12 N10 O11 116.8(8) . . ?
O1 C1 O2 122.4(4) . . ?
O1 C1 C2 117.7(4) . . ?
O2 C1 C2 119.9(4) . . ?
C6 C2 C3 118.7(4) . . ?
C6 C2 C1 119.5(4) . . ?
C3 C2 C1 121.8(4) . . ?
O3 C3 N1 115.6(4) . . ?
O3 C3 C2 127.7(4) . . ?
N1 C3 C2 116.8(4) . . ?
C3 N1 C4 124.6(4) . . ?
C3 N1 H1 117.7 . . ?
C4 N1 H1 117.7 . . ?
C5 C4 N1 118.0(4) . . ?
C5 C4 C40 125.1(5) . . ?
N1 C4 C40 116.9(5) . . ?
C4 C40 H40A 109.5 . . ?
C4 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C4 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C2 C6 C5 121.9(5) . . ?
C2 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
H3WA O3W H3WB 121.8 . . ?
H3WA O3W' H3WB 100.4 . . ?

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
O3 Cu2 O2 C1 -168.0(4) 7_545 . . . ?
O3 Cu2 O2 C1 -4.5(4) . . . . ?
O2W Cu2 O2 C1 97.6(4) 7_545 . . . ?
O2W Cu2 O2 C1 90.1(4) . . . . ?
Cu1 O1 C1 O2 5.8(6) . . . . ?
Cu1 O1 C1 C2 -174.7(2) . . . . ?
Cu2 O2 C1 O1 177.1(3) . . . . ?
Cu2 O2 C1 C2 -2.4(6) . . . . ?
O1 C1 C2 C6 7.0(5) . . . . ?
O2 C1 C2 C6 -173.4(4) . . . . ?
O1 C1 C2 C3 -172.3(3) . . . . ?
O2 C1 C2 C3 7.3(6) . . . . ?
Cu2 O3 C3 N1 173.2(2) . . . . ?
Cu2 O3 C3 C2 -7.4(6) . . . . ?
C6 C2 C3 O3 178.5(4) . . . . ?
C1 C2 C3 O3 -2.2(6) . . . . ?
C6 C2 C3 N1 -2.0(5) . . . . ?
C1 C2 C3 N1 177.2(3) . . . . ?
O3 C3 N1 C4 -178.8(3) . . . . ?
C2 C3 N1 C4 1.7(5) . . . . ?
C3 N1 C4 C5 0.3(6) . . . . ?
C3 N1 C4 C40 -179.7(4) . . . . ?
N1 C4 C5 C6 -1.9(6) . . . . ?
C40 C4 C5 C6 178.1(4) . . . . ?
C3 C2 C6 C5 0.5(5) . . . . ?
C1 C2 C6 C5 -178.7(3) . . . . ?
C4 C5 C6 C2 1.5(6) . . . . ?

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
O1W H1WB O2 1.00 1.81 2.687(9) 143.7 25_655
O1W H1WB O3 1.00 2.55 3.360(8) 137.8 31_655
O2W H2WB O3W 0.88 1.96 2.696(15) 140.1 25_655
O2W H2WB O3W' 0.88 1.99 2.649(15) 130.0 25_655
O2W H2WA O10 0.91 2.02 2.878(7) 156.9 27_655
N1 H1 Cl1 0.88 2.49 3.360(5) 171.2 12_655
N1 H1 O11 0.88 1.85 2.726(9) 170.7 12_655
O3W H3WB Cl1 0.99 2.23 3.181(15) 161.5 .
O3W' H3WB Cl1 1.00 2.23 3.202(16) 163.6 .

_refine_diff_density_max         0.759
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.091

_shelxl_version_number           2013-4

