# 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_datos_0m
_database_code_depnum_ccdc_archive 'CCDC 1416868'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 Cu N8 O8 S2'
_chemical_formula_sum            'C34 H30 Cu N8 O8 S2'
_chemical_formula_weight         806.32

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   11.2861(3)
_cell_length_b                   13.9823(3)
_cell_length_c                   11.9367(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.985(2)
_cell_angle_gamma                90.00
_cell_volume                     1882.55(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6584
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      24.18

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             830
_exptl_absorpt_coefficient_mu    0.751
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8766
_exptl_absorpt_correction_T_max  0.9423
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            26868
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3445
_reflns_number_gt                2481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0719P)²+0.0000P] 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         3445
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1216
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
Cu1 Cu 1.0000 0.5000 1.0000 0.04271(19) Uani 1 2 d S . .
C1 C 0.9153(3) 0.31966(18) 1.0577(2) 0.0414(7) Uani 1 1 d . . .
C6 C 0.7980(3) 0.34544(19) 1.0247(2) 0.0421(7) Uani 1 1 d . . .
C5 C 0.7008(3) 0.2914(2) 1.0628(3) 0.0508(8) Uani 1 1 d . . .
H5 H 0.6243 0.3081 1.0387 0.061 Uiso 1 1 calc R . .
C4 C 0.7166(3) 0.2161(2) 1.1334(3) 0.0566(9) Uani 1 1 d . . .
C3 C 0.8327(3) 0.1897(2) 1.1637(3) 0.0628(9) Uani 1 1 d . . .
H3 H 0.8448 0.1374 1.2107 0.075 Uiso 1 1 calc R . .
C2 C 0.9297(3) 0.2383(2) 1.1266(3) 0.0585(9) Uani 1 1 d . . .
H2 H 1.0056 0.2173 1.1472 0.070 Uiso 1 1 calc R . .
C7 C 0.7993(3) 0.54003(18) 0.8308(2) 0.0372(6) Uani 1 1 d . . .
C8 C 0.8791(3) 0.5701(2) 0.7534(3) 0.0501(8) Uani 1 1 d . . .
H8 H 0.9572 0.5488 0.7581 0.060 Uiso 1 1 calc R . .
C9 C 0.8430(3) 0.6317(2) 0.6692(3) 0.0544(8) Uani 1 1 d . . .
H9 H 0.8960 0.6509 0.6156 0.065 Uiso 1 1 calc R . .
C10 C 0.7280(3) 0.66469(19) 0.6646(2) 0.0435(7) Uani 1 1 d . . .
C11 C 0.6482(3) 0.63583(19) 0.7421(3) 0.0467(7) Uani 1 1 d . . .
H11 H 0.5709 0.6590 0.7386 0.056 Uiso 1 1 calc R . .
C12 C 0.6836(3) 0.57210(19) 0.8255(2) 0.0431(7) Uani 1 1 d . . .
H12 H 0.6298 0.5511 0.8774 0.052 Uiso 1 1 calc R . .
C13 C 0.7683(3) 0.9030(2) 0.6552(3) 0.0476(7) Uani 1 1 d . . .
C14 C 0.6768(3) 0.9276(3) 0.7254(3) 0.0706(10) Uani 1 1 d . . .
H14 H 0.6015 0.9006 0.7263 0.085 Uiso 1 1 calc R . .
C15 C 0.7188(4) 0.9971(3) 0.7902(3) 0.0688(10) Uani 1 1 d . . .
C16 C 0.6729(5) 1.0539(4) 0.8839(4) 0.1176(18) Uani 1 1 d . . .
H16A H 0.5968 1.0296 0.9035 0.176 Uiso 1 1 calc R . .
H16B H 0.6653 1.1196 0.8614 0.176 Uiso 1 1 calc R . .
H16C H 0.7270 1.0494 0.9476 0.176 Uiso 1 1 calc R . .
C17 C 0.6126(3) 0.1604(3) 1.1766(4) 0.0820(12) Uani 1 1 d . . .
H17A H 0.5400 0.1869 1.1461 0.123 Uiso 1 1 calc R . .
H17B H 0.6132 0.1642 1.2569 0.123 Uiso 1 1 calc R . .
H17C H 0.6188 0.0947 1.1542 0.123 Uiso 1 1 calc R . .
H2A H 0.836(3) 0.829(2) 0.546(3) 0.041(10) Uiso 1 1 d . . .
N1 N 0.8610(3) 0.9569(2) 0.6726(3) 0.0701(9) Uani 1 1 d . . .
N2 N 0.7717(3) 0.83678(18) 0.5693(2) 0.0503(7) Uani 1 1 d . . .
N3 N 0.8436(2) 0.47626(14) 0.91772(19) 0.0383(5) Uani 1 1 d . . .
N4 N 0.7661(2) 0.41625(15) 0.94773(19) 0.0430(6) Uani 1 1 d . . .
O1 O 0.8296(2) 1.01817(18) 0.7605(2) 0.0792(8) Uani 1 1 d . . .
O2 O 0.7157(3) 0.70189(16) 0.45153(19) 0.0782(8) Uani 1 1 d . . .
O3 O 0.5666(2) 0.77382(17) 0.5733(2) 0.0745(7) Uani 1 1 d . . .
O4 O 1.00933(16) 0.36631(13) 1.02556(17) 0.0472(5) Uani 1 1 d . . .
S1 S 0.68511(8) 0.74412(5) 0.55524(7) 0.0547(3) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O4 1.8963(18) . ?
Cu1 O4 1.8963(18) 3_767 ?
Cu1 N3 2.017(2) . ?
Cu1 N3 2.017(2) 3_767 ?
C1 O4 1.314(3) . ?
C1 C2 1.410(4) . ?
C1 C6 1.415(4) . ?
C6 N4 1.389(3) . ?
C6 C5 1.420(4) . ?
C5 C4 1.356(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.397(5) . ?
C4 C17 1.514(4) . ?
C3 C2 1.374(4) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C7 C8 1.378(4) . ?
C7 C12 1.381(4) . ?
C7 N3 1.444(3) . ?
C8 C9 1.374(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(4) . ?
C10 S1 1.768(3) . ?
C11 C12 1.384(4) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N1 1.301(4) . ?
C13 N2 1.382(4) . ?
C13 C14 1.396(5) . ?
C14 C15 1.320(5) . ?
C14 H14 0.9300 . ?
C15 O1 1.345(5) . ?
C15 C16 1.480(5) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 O1 1.409(4) . ?
N2 S1 1.628(3) . ?
N2 H2A 0.80(3) . ?
N3 N4 1.272(3) . ?
O2 S1 1.425(3) . ?
O3 S1 1.424(3) . ?

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
O4 Cu1 O4 180.000(2) . 3_767 ?
O4 Cu1 N3 87.64(8) . . ?
O4 Cu1 N3 92.36(8) 3_767 . ?
O4 Cu1 N3 92.35(8) . 3_767 ?
O4 Cu1 N3 87.65(8) 3_767 3_767 ?
N3 Cu1 N3 180.00(11) . 3_767 ?
O4 C1 C2 119.5(3) . . ?
O4 C1 C6 123.3(2) . . ?
C2 C1 C6 117.1(3) . . ?
N4 C6 C1 125.7(3) . . ?
N4 C6 C5 113.9(3) . . ?
C1 C6 C5 120.1(2) . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C4 C3 117.9(3) . . ?
C5 C4 C17 121.6(3) . . ?
C3 C4 C17 120.4(3) . . ?
C2 C3 C4 122.4(3) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C8 C7 C12 120.6(3) . . ?
C8 C7 N3 116.9(2) . . ?
C12 C7 N3 122.5(2) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 S1 120.8(2) . . ?
C9 C10 S1 118.3(2) . . ?
C10 C11 C12 119.5(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C7 C12 C11 119.5(3) . . ?
C7 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
N1 C13 N2 117.6(3) . . ?
N1 C13 C14 111.6(3) . . ?
N2 C13 C14 130.6(3) . . ?
C15 C14 C13 106.0(3) . . ?
C15 C14 H14 127.0 . . ?
C13 C14 H14 127.0 . . ?
C14 C15 O1 109.0(3) . . ?
C14 C15 C16 135.3(4) . . ?
O1 C15 C16 115.8(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 O1 104.5(3) . . ?
C13 N2 S1 125.2(3) . . ?
C13 N2 H2A 113(2) . . ?
S1 N2 H2A 115(2) . . ?
N4 N3 C7 112.7(2) . . ?
N4 N3 Cu1 124.72(18) . . ?
C7 N3 Cu1 121.55(17) . . ?
N3 N4 C6 119.5(2) . . ?
C15 O1 N1 108.8(3) . . ?
C1 O4 Cu1 119.69(16) . . ?
O3 S1 O2 120.60(16) . . ?
O3 S1 N2 108.42(16) . . ?
O2 S1 N2 104.89(16) . . ?
O3 S1 C10 107.82(15) . . ?
O2 S1 C10 108.22(14) . . ?
N2 S1 C10 106.01(14) . . ?

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
N2 H2A O4 0.80(3) 2.03(3) 2.785(4) 157(3) 2_756

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.085
####################################################################### 
# 
# 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_crsx45_0m
_database_code_depnum_ccdc_archive 'CCDC 1416869'
_audit_update_record             
;
2016-01-25 deposited with the CCDC.
2016-03-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H16 N4 O4 S'
_chemical_formula_sum            'C17 H16 N4 O4 S'
_chemical_formula_weight         372.40

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   29.8607(16)
_cell_length_b                   6.3552(4)
_cell_length_c                   17.4730(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.254(3)
_cell_angle_gamma                90.00
_cell_volume                     3301.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      31.03

_exptl_crystal_description       prismatic
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.498
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            87145
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0242
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.37
_diffrn_reflns_theta_max         31.10
_reflns_number_total             5288
_reflns_number_gt                4275
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0572P)²+3.4214P] 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         5288
_refine_ls_number_parameters     249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1013
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.28182(5) -0.0821(2) 0.64603(8) 0.0196(3) Uani 1 1 d . . .
C2 C 0.31656(5) -0.1542(2) 0.69756(8) 0.0227(3) Uani 1 1 d . . .
H2 H 0.3267 -0.2919 0.6942 0.027 Uiso 1 1 calc R . .
C3 C 0.33603(5) -0.0229(2) 0.75358(8) 0.0221(3) Uani 1 1 d . . .
H3 H 0.3593 -0.0743 0.7874 0.026 Uiso 1 1 calc R . .
C4 C 0.32204(5) 0.1854(2) 0.76148(8) 0.0207(3) Uani 1 1 d . . .
C5 C 0.28667(4) 0.2556(2) 0.71182(8) 0.0193(3) Uani 1 1 d . . .
H5 H 0.2761 0.3920 0.7169 0.023 Uiso 1 1 calc R . .
C6 C 0.26639(4) 0.1260(2) 0.65406(8) 0.0176(2) Uani 1 1 d . . .
C7 C 0.17855(4) 0.2015(2) 0.50671(8) 0.0174(2) Uani 1 1 d . . .
C8 C 0.16521(5) 0.4102(2) 0.51552(8) 0.0194(3) Uani 1 1 d . . .
H8 H 0.1797 0.4945 0.5537 0.023 Uiso 1 1 calc R . .
C9 C 0.13031(5) 0.4891(2) 0.46681(8) 0.0196(3) Uani 1 1 d . . .
H9 H 0.1208 0.6273 0.4721 0.024 Uiso 1 1 calc R . .
C10 C 0.10938(4) 0.3608(2) 0.40968(8) 0.0169(2) Uani 1 1 d . . .
C11 C 0.12214(4) 0.1522(2) 0.40138(8) 0.0191(3) Uani 1 1 d . . .
H11 H 0.1074 0.0672 0.3637 0.023 Uiso 1 1 calc R . .
C12 C 0.15721(5) 0.0741(2) 0.45043(8) 0.0203(3) Uani 1 1 d . . .
H12 H 0.1665 -0.0646 0.4455 0.024 Uiso 1 1 calc R . .
C13 C -0.00370(4) 0.2784(2) 0.40851(7) 0.0161(2) Uani 1 1 d . . .
C14 C -0.01123(5) 0.0938(2) 0.36427(8) 0.0191(3) Uani 1 1 d . . .
C15 C -0.04122(4) -0.0154(2) 0.40147(8) 0.0186(2) Uani 1 1 d . . .
C16 C -0.06563(5) -0.2153(2) 0.38603(9) 0.0235(3) Uani 1 1 d . . .
H16A H -0.0571 -0.2755 0.3391 0.035 Uiso 1 1 calc R . .
H16B H -0.0974 -0.1890 0.3813 0.035 Uiso 1 1 calc R . .
H16C H -0.0582 -0.3114 0.4277 0.035 Uiso 1 1 calc R . .
C17 C 0.34644(5) 0.3278(3) 0.81963(9) 0.0282(3) Uani 1 1 d . . .
H17A H 0.3335 0.4662 0.8153 0.042 Uiso 1 1 calc R . .
H17B H 0.3776 0.3348 0.8105 0.042 Uiso 1 1 calc R . .
H17C H 0.3438 0.2738 0.8703 0.042 Uiso 1 1 calc R . .
H14 H 0.0019(6) 0.055(3) 0.3201(11) 0.026(5) Uiso 1 1 d . . .
H2A H 0.0215(7) 0.555(3) 0.4314(12) 0.031(5) Uiso 1 1 d . . .
H4A H 0.2441(9) -0.145(4) 0.5642(16) 0.065(8) Uiso 1 1 d . . .
N1 N -0.02660(4) 0.27846(19) 0.46913(7) 0.0204(2) Uani 1 1 d . . .
N2 N 0.02106(4) 0.45812(19) 0.39596(7) 0.0183(2) Uani 1 1 d . . .
N3 N 0.21421(4) 0.10564(19) 0.55312(7) 0.0183(2) Uani 1 1 d . . .
N4 N 0.23162(4) 0.22027(18) 0.60712(7) 0.0182(2) Uani 1 1 d . . .
O1 O -0.05118(3) 0.08986(16) 0.46494(6) 0.0209(2) Uani 1 1 d . . .
O2 O 0.05768(3) 0.32955(17) 0.28294(6) 0.0224(2) Uani 1 1 d . . .
O3 O 0.07377(3) 0.68428(16) 0.33816(6) 0.0228(2) Uani 1 1 d . . .
O4 O 0.26455(4) -0.21180(17) 0.59004(7) 0.0251(2) Uani 1 1 d . . .
S1 S 0.065382(10) 0.46527(5) 0.347585(18) 0.01732(9) 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 O4 1.3453(18) . ?
C1 C2 1.387(2) . ?
C1 C6 1.4120(19) . ?
C2 C3 1.374(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.399(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(2) . ?
C4 C17 1.499(2) . ?
C5 C6 1.3968(19) . ?
C5 H5 0.9300 . ?
C6 N4 1.3975(17) . ?
C7 C12 1.3836(19) . ?
C7 C8 1.3976(19) . ?
C7 N3 1.4156(17) . ?
C8 C9 1.3783(19) . ?
C8 H8 0.9300 . ?
C9 C10 1.3924(19) . ?
C9 H9 0.9300 . ?
C10 C11 1.3904(19) . ?
C10 S1 1.7559(14) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 N1 1.3123(16) . ?
C13 N2 1.3888(17) . ?
C13 C14 1.4114(18) . ?
C14 C15 1.3465(19) . ?
C14 H14 0.930(19) . ?
C15 O1 1.3514(17) . ?
C15 C16 1.4772(19) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
N1 O1 1.4039(15) . ?
N2 S1 1.6349(11) . ?
N2 H2A 0.87(2) . ?
N3 N4 1.2654(16) . ?
O2 S1 1.4230(10) . ?
O3 S1 1.4265(11) . ?
O4 H4A 0.84(3) . ?

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
O4 C1 C2 118.93(13) . . ?
O4 C1 C6 122.64(13) . . ?
C2 C1 C6 118.43(13) . . ?
C3 C2 C1 120.29(13) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 122.29(13) . . ?
C2 C3 H3 118.9 . . ?
C4 C3 H3 118.9 . . ?
C5 C4 C3 117.55(13) . . ?
C5 C4 C17 121.89(13) . . ?
C3 C4 C17 120.50(13) . . ?
C4 C5 C6 121.39(13) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 N4 114.91(12) . . ?
C5 C6 C1 120.00(13) . . ?
N4 C6 C1 125.09(13) . . ?
C12 C7 C8 121.09(13) . . ?
C12 C7 N3 115.38(12) . . ?
C8 C7 N3 123.53(12) . . ?
C9 C8 C7 118.98(13) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 119.60(12) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 121.60(13) . . ?
C11 C10 S1 119.54(10) . . ?
C9 C10 S1 118.86(10) . . ?
C12 C11 C10 118.48(13) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C7 120.24(13) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
N1 C13 N2 116.84(12) . . ?
N1 C13 C14 111.95(12) . . ?
N2 C13 C14 131.09(12) . . ?
C15 C14 C13 104.10(12) . . ?
C15 C14 H14 127.9(12) . . ?
C13 C14 H14 128.0(12) . . ?
C14 C15 O1 110.31(12) . . ?
C14 C15 C16 133.96(13) . . ?
O1 C15 C16 115.69(12) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C4 C17 H17A 109.5 . . ?
C4 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C4 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C13 N1 O1 105.44(10) . . ?
C13 N2 S1 124.92(9) . . ?
C13 N2 H2A 116.2(13) . . ?
S1 N2 H2A 112.8(13) . . ?
N4 N3 C7 114.55(11) . . ?
N3 N4 C6 115.04(12) . . ?
C15 O1 N1 108.18(10) . . ?
C1 O4 H4A 107.1(19) . . ?
O2 S1 O3 121.14(7) . . ?
O2 S1 N2 108.29(6) . . ?
O3 S1 N2 104.24(6) . . ?
O2 S1 C10 108.58(6) . . ?
O3 S1 C10 108.12(6) . . ?
N2 S1 C10 105.38(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
N2 H2A N1 0.87(2) 2.03(2) 2.8836(17) 166.4(19) 5_566
O4 H4A N3 0.84(3) 1.83(3) 2.5629(16) 145(3) .

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        31.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.484
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.069
