# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_SH370_1
_database_code_depnum_ccdc_archive 'CCDC 1411065'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H19 N O8 S'
_chemical_formula_weight         361.36

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'

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

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

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

_cell_length_a                   6.9329(10)
_cell_length_b                   12.2785(18)
_cell_length_c                   19.091(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.079(5)
_cell_angle_gamma                90
_cell_volume                     1609.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2005
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      21.04

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         18998
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.1429
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.720
_diffrn_reflns_theta_max         25.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3053
_reflns_number_gt                1750
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0432P)²] 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_number_reflns         3053
_refine_ls_number_parameters     250
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1272
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.065
_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
S1 S 0.29873(13) 0.31686(7) 0.11176(4) 0.0344(2) Uani 1 1 d . . . . .
O6 O 0.3009(4) 0.6849(2) 0.26258(12) 0.0488(6) Uani 1 1 d D . . . .
O2 O 0.4347(3) 0.84686(16) 0.17700(11) 0.0435(6) Uani 1 1 d . . . . .
O8 O 0.9265(5) 0.3953(2) 0.24714(16) 0.0722(9) Uani 1 1 d D . . . .
O1 O 0.3470(3) 0.64503(16) 0.12847(12) 0.0369(6) Uani 1 1 d . . . . .
O3 O 0.4746(4) 0.3798(2) 0.12593(11) 0.0571(7) Uani 1 1 d . . . . .
O7 O 1.0110(5) 0.5827(3) 0.31876(16) 0.0718(9) Uani 1 1 d D . . . .
O5 O 0.3208(4) 0.20651(18) 0.13576(11) 0.0592(7) Uani 1 1 d . . . . .
O4 O 0.1361(4) 0.3726(2) 0.13461(11) 0.0604(8) Uani 1 1 d . . . . .
N1 N 0.2649(4) 0.51153(19) 0.01276(15) 0.0286(6) Uani 1 1 d . . . . .
C9 C 0.2333(4) 0.4084(2) -0.02196(14) 0.0259(7) Uani 1 1 d . . . . .
C7 C 0.5106(5) 0.9501(3) 0.20165(17) 0.0480(10) Uani 1 1 d . . . . .
H7A H 0.6117 0.9717 0.1750 0.072 Uiso 1 1 calc R U . . .
H7B H 0.5630 0.9448 0.2508 0.072 Uiso 1 1 calc R U . . .
H7C H 0.4081 1.0033 0.1958 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3670(4) 0.8369(2) 0.10720(16) 0.0311(8) Uani 1 1 d . . . . .
C1 C 0.3280(4) 0.7301(2) 0.08374(16) 0.0294(8) Uani 1 1 d . . . . .
C6 C 0.2724(4) 0.7097(2) 0.01178(15) 0.0271(7) Uani 1 1 d . . . . .
C8 C 0.2403(4) 0.6049(2) -0.01822(16) 0.0284(7) Uani 1 1 d . . . . .
H8 H 0.1958 0.6030 -0.0665 0.034 Uiso 1 1 calc R U . . .
C10 C 0.1924(5) 0.4015(3) -0.09482(16) 0.0392(9) Uani 1 1 d . . . . .
H10 H 0.1909 0.4643 -0.1222 0.047 Uiso 1 1 calc R U . . .
C11 C 0.1544(5) 0.3027(3) -0.12677(16) 0.0425(9) Uani 1 1 d . . . . .
H11 H 0.1249 0.2993 -0.1758 0.051 Uiso 1 1 calc R U . . .
C12 C 0.1588(5) 0.2087(3) -0.08804(17) 0.0392(9) Uani 1 1 d . . . . .
H12 H 0.1310 0.1420 -0.1103 0.047 Uiso 1 1 calc R U . . .
C5 C 0.2447(5) 0.7986(3) -0.03553(16) 0.0383(8) Uani 1 1 d . . . . .
H5 H 0.2061 0.7863 -0.0835 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2742(5) 0.9022(3) -0.01106(17) 0.0438(9) Uani 1 1 d . . . . .
H4 H 0.2515 0.9607 -0.0421 0.053 Uiso 1 1 calc R U . . .
C3 C 0.3380(5) 0.9209(3) 0.05990(17) 0.0395(9) Uani 1 1 d . . . . .
H3 H 0.3616 0.9919 0.0757 0.047 Uiso 1 1 calc R U . . .
C13 C 0.2051(4) 0.2146(2) -0.01549(16) 0.0331(8) Uani 1 1 d . . . . .
H13 H 0.2102 0.1510 0.0111 0.040 Uiso 1 1 calc R U . . .
C14 C 0.2439(4) 0.3130(2) 0.01831(14) 0.0261(7) Uani 1 1 d . . . . .
H1N H 0.309(4) 0.510(2) 0.0578(17) 0.037(10) Uiso 1 1 d . . . . .
H1 H 0.351(5) 0.663(3) 0.1758(19) 0.069(12) Uiso 1 1 d . . . . .
H6OA H 0.400(5) 0.703(4) 0.2959(17) 0.101(17) Uiso 1 1 d D . . . .
H6OB H 0.223(6) 0.639(3) 0.284(2) 0.115(18) Uiso 1 1 d D . . . .
H7OB H 0.905(6) 0.620(4) 0.331(3) 0.16(3) Uiso 1 1 d D . . . .
H8OB H 0.836(5) 0.343(3) 0.243(2) 0.109(18) Uiso 1 1 d D . . . .
H7OA H 0.962(6) 0.521(2) 0.297(2) 0.095(16) Uiso 1 1 d D . . . .
H8OA H 0.991(7) 0.388(4) 0.2095(18) 0.13(2) Uiso 1 1 d 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
S1 O5 1.432(2) . ?
S1 O3 1.437(2) . ?
S1 O4 1.438(2) . ?
S1 C14 1.772(3) . ?
O6 H6OA 0.893(19) . ?
O6 H6OB 0.908(19) . ?
O2 C2 1.355(3) . ?
O2 C7 1.427(4) . ?
O8 H8OB 0.896(19) . ?
O8 H8OA 0.905(19) . ?
O1 C1 1.343(3) . ?
O1 H1 0.93(4) . ?
O7 H7OB 0.92(2) . ?
O7 H7OA 0.904(19) . ?
N1 C8 1.290(4) . ?
N1 C9 1.432(4) . ?
N1 H1N 0.87(3) . ?
C9 C10 1.382(4) . ?
C9 C14 1.397(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C2 C3 1.367(4) . ?
C2 C1 1.400(4) . ?
C1 C6 1.396(4) . ?
C6 C5 1.412(4) . ?
C6 C8 1.414(4) . ?
C8 H8 0.9300 . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.369(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C5 C4 1.361(4) . ?
C5 H5 0.9300 . ?
C4 C3 1.384(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C13 C14 1.379(4) . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O5 S1 O3 113.54(16) . . ?
O5 S1 O4 113.96(15) . . ?
O3 S1 O4 111.57(16) . . ?
O5 S1 C14 107.18(14) . . ?
O3 S1 C14 105.08(13) . . ?
O4 S1 C14 104.57(13) . . ?
H6OA O6 H6OB 106(4) . . ?
C2 O2 C7 117.8(2) . . ?
H8OB O8 H8OA 107(4) . . ?
C1 O1 H1 115(2) . . ?
H7OB O7 H7OA 106(4) . . ?
C8 N1 C9 124.9(3) . . ?
C8 N1 H1N 118.2(19) . . ?
C9 N1 H1N 116.9(19) . . ?
C10 C9 C14 119.3(3) . . ?
C10 C9 N1 121.1(3) . . ?
C14 C9 N1 119.6(3) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C2 C3 125.4(3) . . ?
O2 C2 C1 115.1(3) . . ?
C3 C2 C1 119.5(3) . . ?
O1 C1 C6 118.3(3) . . ?
O1 C1 C2 121.8(3) . . ?
C6 C1 C2 119.8(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 C8 124.6(3) . . ?
C5 C6 C8 116.4(3) . . ?
N1 C8 C6 128.3(3) . . ?
N1 C8 H8 115.8 . . ?
C6 C8 H8 115.8 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.3(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C4 C5 C6 120.2(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C2 C3 C4 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C14 C13 C12 121.3(3) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C9 119.0(3) . . ?
C13 C14 S1 119.7(2) . . ?
C9 C14 S1 121.3(2) . . ?

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
C8 N1 C9 C10 7.1(5) . . . . ?
C8 N1 C9 C14 -172.9(3) . . . . ?
C7 O2 C2 C3 -10.3(4) . . . . ?
C7 O2 C2 C1 168.8(3) . . . . ?
O2 C2 C1 O1 3.4(4) . . . . ?
C3 C2 C1 O1 -177.5(3) . . . . ?
O2 C2 C1 C6 -175.0(3) . . . . ?
C3 C2 C1 C6 4.2(4) . . . . ?
O1 C1 C6 C5 177.7(3) . . . . ?
C2 C1 C6 C5 -3.9(4) . . . . ?
O1 C1 C6 C8 -2.2(4) . . . . ?
C2 C1 C6 C8 176.2(3) . . . . ?
C9 N1 C8 C6 -178.5(3) . . . . ?
C1 C6 C8 N1 -3.9(5) . . . . ?
C5 C6 C8 N1 176.3(3) . . . . ?
C14 C9 C10 C11 2.9(5) . . . . ?
N1 C9 C10 C11 -177.2(3) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C10 C11 C12 C13 -0.8(5) . . . . ?
C1 C6 C5 C4 0.7(5) . . . . ?
C8 C6 C5 C4 -179.4(3) . . . . ?
C6 C5 C4 C3 2.2(5) . . . . ?
O2 C2 C3 C4 177.8(3) . . . . ?
C1 C2 C3 C4 -1.2(5) . . . . ?
C5 C4 C3 C2 -2.0(5) . . . . ?
C11 C12 C13 C14 0.9(5) . . . . ?
C12 C13 C14 C9 0.9(4) . . . . ?
C12 C13 C14 S1 179.0(2) . . . . ?
C10 C9 C14 C13 -2.8(4) . . . . ?
N1 C9 C14 C13 177.3(3) . . . . ?
C10 C9 C14 S1 179.2(2) . . . . ?
N1 C9 C14 S1 -0.7(4) . . . . ?
O5 S1 C14 C13 8.6(3) . . . . ?
O3 S1 C14 C13 129.7(2) . . . . ?
O4 S1 C14 C13 -112.7(3) . . . . ?
O5 S1 C14 C9 -173.4(2) . . . . ?
O3 S1 C14 C9 -52.3(3) . . . . ?
O4 S1 C14 C9 65.3(3) . . . . ?

_refine_diff_density_max         0.328
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_SH281B_2
_database_code_depnum_ccdc_archive 'CCDC 1411066'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H15 Cu N O7 S'
_chemical_formula_weight         404.87

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

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

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

_cell_length_a                   8.599(5)
_cell_length_b                   14.399(5)
_cell_length_c                   12.598(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 96.196(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1550.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3439
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      25.55

_exptl_crystal_description       NEEDLE
_exptl_crystal_colour            BROWN
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_F_000             828
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.581
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.789
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_T_max  0.7892
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17681
_diffrn_reflns_av_unetI/netI     0.0459
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.382
_diffrn_reflns_theta_max         25.707
_diffrn_reflns_theta_full        25.240
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2964
_reflns_number_gt                2213
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0583P)²+0.1589P] 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_number_reflns         2964
_refine_ls_number_parameters     230
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0439
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.15893(5) 0.39869(3) 0.64343(4) 0.03047(16) Uani 1 1 d . . . . .
S2 S 0.47163(11) 0.44760(6) 0.76056(8) 0.0321(2) Uani 1 1 d . . . . .
O1 O -0.1409(3) 0.31660(16) 0.3493(2) 0.0376(7) Uani 1 1 d . . . . .
O6 O 0.5532(3) 0.4213(2) 0.6712(2) 0.0500(8) Uani 1 1 d . . . . .
O7 O 0.5489(3) 0.51421(18) 0.8315(2) 0.0484(8) Uani 1 1 d . . . . .
O2 O 0.0295(3) 0.34698(16) 0.5292(2) 0.0378(7) Uani 1 1 d . . . . .
O3 O 0.0104(3) 0.50313(16) 0.6448(2) 0.0331(6) Uani 1 1 d D . . . .
O5 O 0.3088(3) 0.47745(15) 0.7255(2) 0.0377(7) Uani 1 1 d . . . . .
C6 C 0.1381(4) 0.1934(2) 0.5359(3) 0.0260(8) Uani 1 1 d . . . . .
N1 N 0.2600(3) 0.28177(17) 0.6901(2) 0.0248(6) Uani 1 1 d . . . . .
O4 O 0.2546(3) 0.5263(2) 0.4811(2) 0.0473(7) Uani 1 1 d D . . . .
C14 C 0.4508(4) 0.3441(2) 0.8328(3) 0.0275(8) Uani 1 1 d . . . . .
C2 C -0.0540(4) 0.2431(2) 0.3917(3) 0.0284(8) Uani 1 1 d . . . . .
C1 C 0.0399(4) 0.2640(2) 0.4892(3) 0.0261(8) Uani 1 1 d . . . . .
C3 C -0.0530(4) 0.1558(2) 0.3478(3) 0.0333(9) Uani 1 1 d . . . . .
H3 H -0.1173 0.1426 0.2854 0.040 Uiso 1 1 calc R U . . .
C4 C 0.0445(5) 0.0865(2) 0.3966(3) 0.0355(9) Uani 1 1 d . . . . .
H4 H 0.0450 0.0277 0.3663 0.043 Uiso 1 1 calc R U . . .
C12 C 0.5335(5) 0.2513(3) 0.9868(3) 0.0406(10) Uani 1 1 d . . . . .
H12 H 0.5944 0.2438 1.0518 0.049 Uiso 1 1 calc R U . . .
C11 C 0.4369(4) 0.1808(3) 0.9464(3) 0.0370(9) Uani 1 1 d . . . . .
H11 H 0.4333 0.1254 0.9840 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1378(4) 0.1050(2) 0.4876(3) 0.0331(9) Uani 1 1 d . . . . .
H5 H 0.2028 0.0587 0.5189 0.040 Uiso 1 1 calc R U . . .
C8 C 0.2389(4) 0.2060(2) 0.6321(3) 0.0270(8) Uani 1 1 d . . . . .
H8 H 0.2968 0.1544 0.6569 0.032 Uiso 1 1 calc R U . . .
C13 C 0.5397(4) 0.3337(3) 0.9304(3) 0.0362(9) Uani 1 1 d . . . . .
H13 H 0.6036 0.3819 0.9581 0.043 Uiso 1 1 calc R U . . .
C7 C -0.2238(5) 0.3027(3) 0.2452(3) 0.0480(12) Uani 1 1 d . . . . .
H7A H -0.1504 0.2903 0.1947 0.072 Uiso 1 1 calc R U . . .
H7B H -0.2826 0.3576 0.2240 0.072 Uiso 1 1 calc R U . . .
H7C H -0.2939 0.2510 0.2473 0.072 Uiso 1 1 calc R U . . .
C10 C 0.3457(4) 0.1917(2) 0.8507(3) 0.0319(8) Uani 1 1 d . . . . .
H10 H 0.2778 0.1445 0.8256 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3536(4) 0.2727(2) 0.7908(3) 0.0248(8) Uani 1 1 d . . . . .
H30A H 0.063(4) 0.5577(15) 0.634(3) 0.037 Uiso 1 1 d D U . . .
H30B H -0.084(3) 0.494(2) 0.599(2) 0.037 Uiso 1 1 d D U . . .
H40A H 0.233(4) 0.5842(15) 0.502(3) 0.037 Uiso 1 1 d D U . . .
H40B H 0.313(4) 0.540(2) 0.426(2) 0.037 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
Cu1 O2 1.876(2) . ?
Cu1 O5 1.931(2) . ?
Cu1 N1 1.956(3) . ?
Cu1 O3 1.974(3) . ?
S2 O7 1.426(3) . ?
S2 O6 1.439(3) . ?
S2 O5 1.485(3) . ?
S2 C14 1.766(3) . ?
O1 C2 1.371(4) . ?
O1 C7 1.437(4) . ?
O2 C1 1.303(4) . ?
C6 C1 1.409(4) . ?
C6 C5 1.410(4) . ?
C6 C8 1.424(4) . ?
N1 C8 1.315(4) . ?
N1 C9 1.432(4) . ?
C14 C13 1.384(5) . ?
C14 C9 1.393(4) . ?
C2 C3 1.374(5) . ?
C2 C1 1.427(4) . ?
C3 C4 1.401(5) . ?
C4 C5 1.354(5) . ?
C12 C11 1.374(5) . ?
C12 C13 1.387(5) . ?
C11 C10 1.374(5) . ?
C10 C9 1.395(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O5 161.87(12) . . ?
O2 Cu1 N1 95.55(11) . . ?
O5 Cu1 N1 95.46(11) . . ?
O2 Cu1 O3 88.75(11) . . ?
O5 Cu1 O3 86.74(11) . . ?
N1 Cu1 O3 156.90(12) . . ?
O7 S2 O6 115.68(18) . . ?
O7 S2 O5 110.64(16) . . ?
O6 S2 O5 111.50(17) . . ?
O7 S2 C14 108.13(16) . . ?
O6 S2 C14 105.45(17) . . ?
O5 S2 C14 104.65(16) . . ?
C2 O1 C7 116.4(3) . . ?
C1 O2 Cu1 126.9(2) . . ?
S2 O5 Cu1 122.87(15) . . ?
C1 C6 C5 119.9(3) . . ?
C1 C6 C8 123.1(3) . . ?
C5 C6 C8 117.0(3) . . ?
C8 N1 C9 116.6(3) . . ?
C8 N1 Cu1 121.1(2) . . ?
C9 N1 Cu1 122.3(2) . . ?
C13 C14 C9 120.6(3) . . ?
C13 C14 S2 118.2(3) . . ?
C9 C14 S2 121.1(3) . . ?
O1 C2 C3 125.2(3) . . ?
O1 C2 C1 114.0(3) . . ?
C3 C2 C1 120.8(3) . . ?
O2 C1 C6 124.3(3) . . ?
O2 C1 C2 118.0(3) . . ?
C6 C1 C2 117.7(3) . . ?
C2 C3 C4 120.3(3) . . ?
C5 C4 C3 120.2(3) . . ?
C11 C12 C13 119.8(3) . . ?
C12 C11 C10 120.3(3) . . ?
C4 C5 C6 121.1(3) . . ?
N1 C8 C6 127.9(3) . . ?
C14 C13 C12 119.9(3) . . ?
C11 C10 C9 121.0(3) . . ?
C14 C9 C10 118.2(3) . . ?
C14 C9 N1 121.7(3) . . ?
C10 C9 N1 120.0(3) . . ?

_refine_diff_density_max         0.470
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.099

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_SH619_3
_database_code_depnum_ccdc_archive 'CCDC 1411067'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H28 Cu N4 O7 S'
_chemical_formula_weight         616.13

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      Triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9237(2)
_cell_length_b                   11.2344(4)
_cell_length_c                   16.0644(5)
_cell_angle_alpha                103.893(1)
_cell_angle_beta                 96.378(2)
_cell_angle_gamma                94.347(1)
_cell_volume                     1371.79(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    7787
_cell_measurement_theta_min      2.55
_cell_measurement_theta_max      26.02

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_F_000             638
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.925
_shelx_estimated_absorpt_T_min   0.802
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8018
_exptl_absorpt_correction_T_max  0.8588
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23731
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.551
_diffrn_reflns_theta_max         26.191
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5473
_reflns_number_gt                4452
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0600P)²+0.7340P] 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_number_reflns         5473
_refine_ls_number_parameters     370
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0563
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1125
_refine_ls_wR_factor_gt          0.1034
_refine_ls_goodness_of_fit_ref   1.072
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6380(3) 0.1099(2) 0.32863(17) 0.0361(6) Uani 1 1 d . . . . .
C2 C 0.7821(3) 0.0464(2) 0.34644(19) 0.0414(6) Uani 1 1 d . . . . .
C3 C 0.9123(4) 0.1023(3) 0.4100(2) 0.0526(8) Uani 1 1 d . . . . .
H3 H 1.0031 0.0585 0.4221 0.063 Uiso 1 1 calc R U . . .
C4 C 0.9116(4) 0.2236(3) 0.4570(2) 0.0605(9) Uani 1 1 d . . . . .
H4 H 1.0009 0.2604 0.5004 0.073 Uiso 1 1 calc R U . . .
C5 C 0.7790(4) 0.2883(3) 0.4392(2) 0.0528(8) Uani 1 1 d . . . . .
H5 H 0.7799 0.3699 0.4698 0.063 Uiso 1 1 calc R U . . .
C6 C 0.6408(3) 0.2331(2) 0.37494(17) 0.0370(6) Uani 1 1 d . . . . .
C7 C 0.9151(5) -0.1382(3) 0.3018(3) 0.0695(10) Uani 1 1 d . . . . .
H7A H 1.0171 -0.0906 0.2961 0.104 Uiso 1 1 calc R U . . .
H7B H 0.8974 -0.2136 0.2571 0.104 Uiso 1 1 calc R U . . .
H7C H 0.9266 -0.1566 0.3574 0.104 Uiso 1 1 calc R U . . .
C8 C 0.5099(3) 0.3078(2) 0.35642(17) 0.0376(6) Uani 1 1 d . . . . .
H8 H 0.5217 0.3889 0.3895 0.045 Uiso 1 1 calc R U . . .
C9 C 0.2685(3) 0.3676(2) 0.28913(17) 0.0355(6) Uani 1 1 d . . . . .
C10 C 0.1806(4) 0.4200(3) 0.3564(2) 0.0475(7) Uani 1 1 d . . . . .
H10 H 0.2040 0.4030 0.4101 0.057 Uiso 1 1 calc R U . . .
C11 C 0.0585(4) 0.4976(3) 0.3436(2) 0.0599(9) Uani 1 1 d . . . . .
H11 H -0.0014 0.5319 0.3885 0.072 Uiso 1 1 calc R U . . .
C12 C 0.0258(4) 0.5237(3) 0.2650(2) 0.0614(9) Uani 1 1 d . . . . .
H12 H -0.0595 0.5736 0.2560 0.074 Uiso 1 1 calc R U . . .
C13 C 0.1178(4) 0.4770(3) 0.1986(2) 0.0513(8) Uani 1 1 d . . . . .
H13 H 0.0974 0.4982 0.1461 0.062 Uiso 1 1 calc R U . . .
C14 C 0.2404(3) 0.3986(2) 0.20993(18) 0.0377(6) Uani 1 1 d . . . . .
C15 C -0.0533(3) 0.1801(3) 0.20547(19) 0.0415(6) Uani 1 1 d . . . . .
H15 H -0.0155 0.2479 0.2516 0.050 Uiso 1 1 calc R U . . .
C16 C -0.2172(4) 0.1724(3) 0.1636(2) 0.0468(7) Uani 1 1 d . . . . .
H16 H -0.2866 0.2347 0.1803 0.056 Uiso 1 1 calc R U . . .
C17 C -0.2752(4) 0.0718(3) 0.0974(2) 0.0531(8) Uani 1 1 d . . . . .
H17 H -0.3844 0.0653 0.0676 0.064 Uiso 1 1 calc R U . . .
C18 C -0.1707(4) -0.0204(3) 0.07500(19) 0.0484(7) Uani 1 1 d . . . . .
H18 H -0.2098 -0.0910 0.0313 0.058 Uiso 1 1 calc R U . . .
C19 C -0.0063(3) -0.0059(2) 0.11863(16) 0.0359(6) Uani 1 1 d . . . . .
C20 C 0.1146(3) -0.0996(2) 0.09848(17) 0.0367(6) Uani 1 1 d . . . . .
C21 C 0.0683(4) -0.2163(3) 0.0437(2) 0.0549(8) Uani 1 1 d . . . . .
H21 H -0.0436 -0.2395 0.0170 0.066 Uiso 1 1 calc R U . . .
C22 C 0.1902(5) -0.2970(3) 0.0296(2) 0.0646(9) Uani 1 1 d . . . . .
H22 H 0.1619 -0.3755 -0.0070 0.078 Uiso 1 1 calc R U . . .
C23 C 0.3543(5) -0.2604(3) 0.0702(2) 0.0621(9) Uani 1 1 d . . . . .
H23 H 0.4386 -0.3135 0.0613 0.075 Uiso 1 1 calc R U . . .
C24 C 0.3921(4) -0.1437(3) 0.1242(2) 0.0498(7) Uani 1 1 d . . . . .
H24 H 0.5034 -0.1190 0.1514 0.060 Uiso 1 1 calc R U . . .
C25 C 0.5966(7) 0.6403(5) 0.3818(4) 0.1023(16) Uani 1 1 d D . . . .
H25 H 0.5653 0.5796 0.3305 0.123 Uiso 1 1 calc DR U . . .
C26 C 0.5771(10) 0.8410(5) 0.4622(5) 0.161(3) Uani 1 1 d . . . . .
H26A H 0.6423 0.8117 0.5058 0.241 Uiso 1 1 calc R U . . .
H26B H 0.4756 0.8707 0.4834 0.241 Uiso 1 1 calc R U . . .
H26C H 0.6444 0.9067 0.4486 0.241 Uiso 1 1 calc R U . . .
C27 C 0.4101(10) 0.7682(9) 0.3254(8) 0.273(8) Uani 1 1 d . . . . .
H27A H 0.3981 0.7034 0.2732 0.410 Uiso 1 1 calc R U . . .
H27B H 0.4460 0.8451 0.3133 0.410 Uiso 1 1 calc R U . . .
H27C H 0.3024 0.7734 0.3474 0.410 Uiso 1 1 calc R U . . .
N1 N 0.3767(3) 0.27403(18) 0.29840(13) 0.0325(4) Uani 1 1 d . . . . .
N2 N 0.0545(3) 0.09474(19) 0.18296(14) 0.0345(5) Uani 1 1 d . . . . .
N3 N 0.2743(3) -0.06462(19) 0.13892(15) 0.0378(5) Uani 1 1 d . . . . .
N4 N 0.5314(4) 0.7431(3) 0.3867(3) 0.0822(11) Uani 1 1 d . . . . .
O1 O 0.5144(2) 0.05082(17) 0.26954(13) 0.0460(5) Uani 1 1 d . . . . .
O2 O 0.7737(3) -0.06979(19) 0.29409(15) 0.0578(6) Uani 1 1 d . . . . .
O3 O 0.3520(3) 0.20941(17) 0.11137(12) 0.0454(5) Uani 1 1 d . . . . .
O4 O 0.2960(3) 0.3839(2) 0.05293(15) 0.0635(6) Uani 1 1 d . . . . .
O5 O 0.5393(3) 0.39946(19) 0.16188(15) 0.0539(5) Uani 1 1 d . . . . .
O6 O 0.6947(5) 0.6139(3) 0.4371(2) 0.1022(11) Uani 1 1 d D . . . .
O7 O 0.2545(4) 0.4032(3) 0.8785(2) 0.0927(10) Uani 1 1 d D . . . .
S1 S 0.36793(9) 0.34391(6) 0.12688(4) 0.04018(17) Uani 1 1 d . . . . .
Cu1 Cu 0.31548(4) 0.10535(3) 0.22041(2) 0.03377(12) Uani 1 1 d . . . . .
H1A H 0.323(3) 0.458(2) 0.8734(18) 0.051 Uiso 1 1 d D U . . .
H1B H 0.283(4) 0.395(3) 0.9272(10) 0.051 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
C1 O1 1.301(3) . ?
C1 C6 1.402(4) . ?
C1 C2 1.430(4) . ?
C2 C3 1.365(4) . ?
C2 O2 1.365(3) . ?
C3 C4 1.391(5) . ?
C4 C5 1.365(4) . ?
C5 C6 1.410(4) . ?
C6 C8 1.432(4) . ?
C7 O2 1.416(4) . ?
C8 N1 1.295(3) . ?
C9 C10 1.386(4) . ?
C9 C14 1.397(4) . ?
C9 N1 1.430(3) . ?
C10 C11 1.381(4) . ?
C11 C12 1.366(5) . ?
C12 C13 1.380(5) . ?
C13 C14 1.386(4) . ?
C14 S1 1.783(3) . ?
C15 N2 1.344(3) . ?
C15 C16 1.381(4) . ?
C16 C17 1.361(4) . ?
C17 C18 1.381(4) . ?
C18 C19 1.387(4) . ?
C19 N2 1.351(3) . ?
C19 C20 1.479(4) . ?
C20 N3 1.341(3) . ?
C20 C21 1.389(4) . ?
C21 C22 1.375(5) . ?
C22 C23 1.373(5) . ?
C23 C24 1.378(4) . ?
C24 N3 1.338(3) . ?
C25 O6 1.221(5) . ?
C25 N4 1.289(6) . ?
C26 N4 1.418(8) . ?
C27 N4 1.392(7) . ?
N1 Cu1 1.995(2) . ?
N2 Cu1 2.075(2) . ?
N3 Cu1 2.019(2) . ?
O1 Cu1 1.893(2) . ?
O3 S1 1.464(2) . ?
O3 Cu1 2.359(2) . ?
O4 S1 1.443(2) . ?
O5 S1 1.443(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 118.1(2) . . ?
C6 C1 C2 117.7(2) . . ?
C3 C2 O2 125.8(3) . . ?
C3 C2 C1 120.6(3) . . ?
O2 C2 C1 113.5(2) . . ?
C2 C3 C4 121.1(3) . . ?
C5 C4 C3 119.6(3) . . ?
C4 C5 C6 120.9(3) . . ?
C1 C6 C5 120.0(2) . . ?
C1 C6 C8 121.8(2) . . ?
C5 C6 C8 118.2(2) . . ?
N1 C8 C6 126.8(2) . . ?
C10 C9 C14 120.0(2) . . ?
C10 C9 N1 119.9(2) . . ?
C14 C9 N1 119.9(2) . . ?
C11 C10 C9 120.0(3) . . ?
C12 C11 C10 119.9(3) . . ?
C11 C12 C13 120.8(3) . . ?
C12 C13 C14 120.2(3) . . ?
C13 C14 C9 119.0(3) . . ?
C13 C14 S1 120.7(2) . . ?
C9 C14 S1 120.28(19) . . ?
N2 C15 C16 123.4(3) . . ?
C17 C16 C15 118.7(3) . . ?
C16 C17 C18 119.5(3) . . ?
C17 C18 C19 118.9(3) . . ?
N2 C19 C18 122.3(2) . . ?
N2 C19 C20 115.2(2) . . ?
C18 C19 C20 122.5(2) . . ?
N3 C20 C21 121.6(3) . . ?
N3 C20 C19 114.8(2) . . ?
C21 C20 C19 123.6(3) . . ?
C22 C21 C20 119.1(3) . . ?
C23 C22 C21 119.2(3) . . ?
C22 C23 C24 119.1(3) . . ?
N3 C24 C23 122.3(3) . . ?
O6 C25 N4 127.1(5) . . ?
C8 N1 C9 116.3(2) . . ?
C8 N1 Cu1 125.4(2) . . ?
C9 N1 Cu1 118.3(2) . . ?
C15 N2 C19 117.1(2) . . ?
C15 N2 Cu1 128.9(2) . . ?
C19 N2 Cu1 113.3(2) . . ?
C24 N3 C20 118.7(2) . . ?
C24 N3 Cu1 125.1(2) . . ?
C20 N3 Cu1 116.1(2) . . ?
C25 N4 C27 126.2(7) . . ?
C25 N4 C26 119.4(5) . . ?
C27 N4 C26 114.3(7) . . ?
C1 O1 Cu1 130.91(17) . . ?
C2 O2 C7 118.4(3) . . ?
S1 O3 Cu1 123.45(11) . . ?
O4 S1 O5 114.05(14) . . ?
O4 S1 O3 112.50(14) . . ?
O5 S1 O3 112.41(12) . . ?
O4 S1 C14 105.54(14) . . ?
O5 S1 C14 105.22(13) . . ?
O3 S1 C14 106.27(12) . . ?
O1 Cu1 N1 90.73(8) . . ?
O1 Cu1 N3 86.06(8) . . ?
N1 Cu1 N3 175.05(9) . . ?
O1 Cu1 N2 153.73(9) . . ?
N1 Cu1 N2 104.72(8) . . ?
N3 Cu1 N2 79.66(8) . . ?
O1 Cu1 O3 116.12(8) . . ?
N1 Cu1 O3 82.97(7) . . ?
N3 Cu1 O3 95.06(8) . . ?
N2 Cu1 O3 87.22(8) . . ?

_refine_diff_density_max         0.664
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.078

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_SH290_4
_database_code_depnum_ccdc_archive 'CCDC 1411068'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H32 Cu2 N4 O10 S2'
_chemical_formula_weight         895.92

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.149(2)
_cell_length_b                   16.476(5)
_cell_length_c                   13.478(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.476(10)
_cell_angle_gamma                90
_cell_volume                     1804.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3405
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      22.43

_exptl_crystal_description       Hexagonal
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_F_000             916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.362
_shelx_estimated_absorpt_T_min   0.727
_shelx_estimated_absorpt_T_max   0.822
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.719
_exptl_absorpt_correction_T_max  0.815
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25898
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.472
_diffrn_reflns_theta_max         25.334
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3260
_reflns_number_gt                2437
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0433P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     254
_refine_ls_number_restraints     81
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0807
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.63034(5) 0.57569(2) 0.50589(3) 0.02828(14) Uani 1 1 d . U . . .
S002 S 0.70750(12) 0.75065(5) 0.54745(6) 0.0390(2) Uani 1 1 d . U . . .
O1 O 0.6020(3) 0.48002(12) 0.42635(15) 0.0302(5) Uani 1 1 d . U . . .
O3 O 0.6758(3) 0.67003(13) 0.59107(16) 0.0441(6) Uani 1 1 d . U . . .
O2 O 0.7282(3) 0.34978(14) 0.35380(18) 0.0492(7) Uani 1 1 d . U . . .
N2 N 0.7920(3) 0.51341(16) 0.59980(19) 0.0323(6) Uani 1 1 d . U . . .
N1 N 0.5172(3) 0.64317(15) 0.39653(19) 0.0284(6) Uani 1 1 d . U . . .
O4 O 0.8266(3) 0.74521(17) 0.4747(2) 0.0563(7) Uani 1 1 d . U . . .
O5 O 0.7396(4) 0.81079(15) 0.6234(2) 0.0635(8) Uani 1 1 d . U . . .
C8 C 0.5047(4) 0.61898(19) 0.3053(2) 0.0294(7) Uani 1 1 d . U . . .
H8 H 0.4538 0.6545 0.2590 0.035 Uiso 1 1 calc R U . . .
C6 C 0.5606(4) 0.54343(19) 0.2672(2) 0.0292(7) Uani 1 1 d . U . . .
C1 C 0.6118(4) 0.47828(19) 0.3300(2) 0.0278(7) Uani 1 1 d . U . . .
C9 C 0.4428(4) 0.72043(19) 0.4149(2) 0.0307(7) Uani 1 1 d . U . . .
C2 C 0.6751(4) 0.40777(19) 0.2859(2) 0.0330(8) Uani 1 1 d . U . . .
C15 C 0.8238(4) 0.5359(2) 0.6944(3) 0.0421(9) Uani 1 1 d . U . . .
H15 H 0.7684 0.5806 0.7174 0.051 Uiso 1 1 calc R U . . .
C14 C 0.5184(4) 0.77469(19) 0.4835(2) 0.0328(8) Uani 1 1 d . U . . .
C5 C 0.5659(5) 0.5353(2) 0.1632(2) 0.0400(9) Uani 1 1 d . U . . .
H5 H 0.5290 0.5775 0.1215 0.048 Uiso 1 1 calc R U . . .
C3 C 0.6801(4) 0.4017(2) 0.1850(3) 0.0420(9) Uani 1 1 d . U . . .
H3 H 0.7204 0.3548 0.1571 0.050 Uiso 1 1 calc R U . . .
C4 C 0.6243(5) 0.4664(2) 0.1236(3) 0.0454(9) Uani 1 1 d . U . . .
H4 H 0.6274 0.4620 0.0549 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4454(5) 0.8496(2) 0.5003(3) 0.0481(10) Uani 1 1 d . U . . .
H13 H 0.4973 0.8863 0.5448 0.058 Uiso 1 1 calc R U . . .
C10 C 0.2929(4) 0.7414(2) 0.3660(3) 0.0419(9) Uani 1 1 d . U . . .
H10 H 0.2407 0.7057 0.3203 0.050 Uiso 1 1 calc R U . . .
C19 C 0.8767(4) 0.4490(2) 0.5685(3) 0.0410(9) Uani 1 1 d . U . . .
H19 H 0.8563 0.4319 0.5030 0.049 Uiso 1 1 calc R U . . .
C18 C 0.9914(4) 0.4078(2) 0.6291(3) 0.0488(10) Uani 1 1 d . U . . .
H18 H 1.0487 0.3643 0.6046 0.059 Uiso 1 1 calc R U . . .
C17 C 1.0200(5) 0.4319(2) 0.7261(3) 0.0531(10) Uani 1 1 d . U . . .
H17 H 1.0967 0.4049 0.7689 0.064 Uiso 1 1 calc R U . . .
C12 C 0.2960(5) 0.8689(3) 0.4508(3) 0.0572(11) Uani 1 1 d . U . . .
H12 H 0.2464 0.9185 0.4624 0.069 Uiso 1 1 calc R U . . .
C16 C 0.9338(5) 0.4964(3) 0.7591(3) 0.0535(10) Uani 1 1 d . U . . .
H16 H 0.9499 0.5132 0.8250 0.064 Uiso 1 1 calc R U . . .
C11 C 0.2208(5) 0.8150(3) 0.3847(3) 0.0546(11) Uani 1 1 d . U . . .
H11 H 0.1197 0.8282 0.3519 0.065 Uiso 1 1 calc R U . . .
C7 C 0.8049(7) 0.2797(3) 0.3176(4) 0.0799(15) Uani 1 1 d . U . . .
H7A H 0.7269 0.2502 0.2744 0.120 Uiso 1 1 calc R U . . .
H7B H 0.8432 0.2459 0.3726 0.120 Uiso 1 1 calc R U . . .
H7C H 0.8964 0.2956 0.2813 0.120 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.910(2) . ?
Cu1 O3 1.951(2) . ?
Cu1 N1 2.012(3) . ?
Cu1 N2 2.032(3) . ?
Cu1 O1 2.352(2) 3_666 ?
S002 O5 1.434(3) . ?
S002 O4 1.435(3) . ?
S002 O3 1.483(2) . ?
S002 C14 1.751(4) . ?
O1 C1 1.307(3) . ?
O1 Cu1 2.352(2) 3_666 ?
O2 C2 1.369(4) . ?
O2 C7 1.417(4) . ?
N2 C15 1.333(4) . ?
N2 C19 1.351(4) . ?
N1 C8 1.289(4) . ?
N1 C9 1.440(4) . ?
C8 C6 1.434(4) . ?
C6 C1 1.410(4) . ?
C6 C5 1.413(4) . ?
C1 C2 1.420(4) . ?
C9 C10 1.386(5) . ?
C9 C14 1.394(5) . ?
C2 C3 1.368(5) . ?
C15 C16 1.366(5) . ?
C14 C13 1.396(5) . ?
C5 C4 1.356(5) . ?
C3 C4 1.404(5) . ?
C13 C12 1.379(6) . ?
C10 C11 1.380(5) . ?
C19 C18 1.372(5) . ?
C18 C17 1.370(6) . ?
C17 C16 1.367(5) . ?
C12 C11 1.369(6) . ?

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 O3 175.55(10) . . ?
O1 Cu1 N1 90.94(10) . . ?
O3 Cu1 N1 92.63(10) . . ?
O1 Cu1 N2 88.68(10) . . ?
O3 Cu1 N2 87.23(10) . . ?
N1 Cu1 N2 166.69(11) . . ?
O1 Cu1 O1 80.23(9) . 3_666 ?
O3 Cu1 O1 101.77(9) . 3_666 ?
N1 Cu1 O1 99.40(9) . 3_666 ?
N2 Cu1 O1 93.65(9) . 3_666 ?
O5 S002 O4 115.79(18) . . ?
O5 S002 O3 111.33(16) . . ?
O4 S002 O3 111.27(16) . . ?
O5 S002 C14 107.43(16) . . ?
O4 S002 C14 107.09(16) . . ?
O3 S002 C14 102.94(15) . . ?
C1 O1 Cu1 124.16(19) . . ?
C1 O1 Cu1 119.35(19) . 3_666 ?
Cu1 O1 Cu1 99.77(9) . 3_666 ?
S002 O3 Cu1 120.75(14) . . ?
C2 O2 C7 117.6(3) . . ?
C15 N2 C19 116.8(3) . . ?
C15 N2 Cu1 121.6(2) . . ?
C19 N2 Cu1 121.6(2) . . ?
C8 N1 C9 115.8(3) . . ?
C8 N1 Cu1 121.7(2) . . ?
C9 N1 Cu1 122.5(2) . . ?
N1 C8 C6 127.3(3) . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 C8 122.2(3) . . ?
C5 C6 C8 118.2(3) . . ?
O1 C1 C6 122.8(3) . . ?
O1 C1 C2 119.0(3) . . ?
C6 C1 C2 118.2(3) . . ?
C10 C9 C14 118.9(3) . . ?
C10 C9 N1 120.4(3) . . ?
C14 C9 N1 120.7(3) . . ?
C3 C2 O2 125.5(3) . . ?
C3 C2 C1 121.1(3) . . ?
O2 C2 C1 113.4(3) . . ?
N2 C15 C16 123.2(4) . . ?
C9 C14 C13 120.2(3) . . ?
C9 C14 S002 120.5(2) . . ?
C13 C14 S002 119.3(3) . . ?
C4 C5 C6 120.6(3) . . ?
C2 C3 C4 119.8(3) . . ?
C5 C4 C3 120.7(3) . . ?
C12 C13 C14 119.8(4) . . ?
C11 C10 C9 120.3(4) . . ?
N2 C19 C18 122.9(4) . . ?
C17 C18 C19 118.8(4) . . ?
C16 C17 C18 118.8(4) . . ?
C11 C12 C13 119.9(4) . . ?
C15 C16 C17 119.4(4) . . ?
C12 C11 C10 120.9(4) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.075

_shelxl_version_number           2014-1

####################################################################### 
# 
# 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_SH284A_5
_database_code_depnum_ccdc_archive 'CCDC 1411069'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-10-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H38 Cu2 N2 O14 S2'
_chemical_formula_weight         865.84

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   7.7522(10)
_cell_length_b                   17.119(2)
_cell_length_c                   13.2121(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.839(4)
_cell_angle_gamma                90
_cell_volume                     1751.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      26.35

_exptl_crystal_description       Needle
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.642
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    1.406
_shelx_estimated_absorpt_T_min   0.720
_shelx_estimated_absorpt_T_max   0.796
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.711
_exptl_absorpt_correction_T_max  0.787
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II PHOTON'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30546
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.379
_diffrn_reflns_theta_max         26.432
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3592
_reflns_number_gt                3270
_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 SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-1997 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0445P)²+1.2802P] 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_number_reflns         3592
_refine_ls_number_parameters     246
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.002
_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 0.14356(3) 0.92651(2) 1.00960(2) 0.02701(9) Uani 1 1 d . . . . .
S1 S 0.23245(7) 0.75860(3) 1.04568(4) 0.03321(14) Uani 1 1 d . . . . .
O6 O 0.26083(19) 0.99195(8) 1.11693(11) 0.0305(3) Uani 1 1 d D . . . .
O3 O 0.1984(2) 0.83503(8) 1.09404(11) 0.0369(4) Uani 1 1 d . . . . .
O4 O 0.3556(2) 0.76608(10) 0.96779(14) 0.0466(4) Uani 1 1 d . . . . .
O5 O 0.2715(3) 0.69917(10) 1.11983(14) 0.0557(5) Uani 1 1 d . . . . .
N1 N 0.0332(2) 0.86281(9) 0.89890(12) 0.0256(3) Uani 1 1 d . . . . .
O2 O 0.2340(2) 1.15046(9) 0.85203(12) 0.0428(4) Uani 1 1 d . . . . .
O1 O 0.13461(19) 1.01997(8) 0.93078(10) 0.0299(3) Uani 1 1 d . . . . .
O7 O 0.4544(3) 0.09541(12) 0.02499(16) 0.0569(5) Uani 1 1 d D . . . .
C6 C 0.0859(3) 0.95941(12) 0.76746(14) 0.0272(4) Uani 1 1 d . . . . .
C1 C 0.1361(2) 1.02206(11) 0.83100(14) 0.0256(4) Uani 1 1 d . . . . .
C15 C 0.3467(4) 0.96288(15) 1.20847(19) 0.0468(6) Uani 1 1 d . . . . .
H15A H 0.4419 0.9295 1.1910 0.056 Uiso 1 1 calc R U . . .
H15B H 0.2663 0.9314 1.2450 0.056 Uiso 1 1 calc R U . . .
C16 C 0.4139(4) 1.02708(16) 1.2754(2) 0.0533(7) Uani 1 1 d . . . . .
H16A H 0.4986 1.0565 1.2410 0.080 Uiso 1 1 calc R U . . .
H16B H 0.4659 1.0053 1.3365 0.080 Uiso 1 1 calc R U . . .
H16C H 0.3204 1.0608 1.2919 0.080 Uiso 1 1 calc R U . . .
C14 C 0.0337(3) 0.73508(12) 0.98309(14) 0.0279(4) Uani 1 1 d . . . . .
C9 C -0.0462(3) 0.78889(11) 0.91686(14) 0.0270(4) Uani 1 1 d . . . . .
C8 C 0.0274(3) 0.88604(11) 0.80523(14) 0.0270(4) Uani 1 1 d . . . . .
H8 H -0.0199 0.8513 0.7574 0.032 Uiso 1 1 calc R U . . .
C5 C 0.0858(3) 0.96789(14) 0.66064(15) 0.0350(5) Uani 1 1 d . . . . .
H5 H 0.0514 0.9264 0.6189 0.042 Uiso 1 1 calc R U . . .
C4 C 0.1357(3) 1.03650(14) 0.61901(16) 0.0394(5) Uani 1 1 d . . . . .
H4 H 0.1366 1.0415 0.5489 0.047 Uiso 1 1 calc R U . . .
C3 C 0.1857(3) 1.09953(13) 0.68091(17) 0.0364(5) Uani 1 1 d . . . . .
H3 H 0.2192 1.1462 0.6518 0.044 Uiso 1 1 calc R U . . .
C2 C 0.1856(3) 1.09291(12) 0.78460(16) 0.0298(4) Uani 1 1 d . . . . .
C7 C 0.2879(4) 1.22324(15) 0.8128(2) 0.0596(8) Uani 1 1 d . . . . .
H7A H 0.3813 1.2148 0.7689 0.089 Uiso 1 1 calc R U . . .
H7B H 0.3260 1.2568 0.8677 0.089 Uiso 1 1 calc R U . . .
H7C H 0.1930 1.2473 0.7752 0.089 Uiso 1 1 calc R U . . .
C10 C -0.2035(3) 0.76921(14) 0.86836(17) 0.0370(5) Uani 1 1 d . . . . .
H10 H -0.2600 0.8050 0.8253 0.044 Uiso 1 1 calc R U . . .
C11 C -0.2762(3) 0.69678(15) 0.8838(2) 0.0448(6) Uani 1 1 d . . . . .
H11 H -0.3807 0.6840 0.8502 0.054 Uiso 1 1 calc R U . . .
C12 C -0.1966(3) 0.64328(15) 0.94810(19) 0.0450(6) Uani 1 1 d . . . . .
H12 H -0.2465 0.5946 0.9577 0.054 Uiso 1 1 calc R U . . .
C13 C -0.0410(3) 0.66244(13) 0.99861(17) 0.0382(5) Uani 1 1 d . . . . .
H13 H 0.0132 0.6268 1.0427 0.046 Uiso 1 1 calc R U . . .
H6E H 0.324(4) 1.0271(14) 1.089(2) 0.057 Uiso 1 1 d D U . . .
H7WA H 0.501(4) 0.1388(12) 0.040(2) 0.057 Uiso 1 1 d D U . . .
H7WB H 0.384(3) 0.108(2) -0.0222(19) 0.057 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
Cu1 O1 1.9085(14) . ?
Cu1 O3 1.9573(15) . ?
Cu1 N1 1.9841(16) . ?
Cu1 O6 1.9912(14) . ?
S1 O5 1.4342(17) . ?
S1 O4 1.4438(19) . ?
S1 O3 1.4854(16) . ?
S1 C14 1.759(2) . ?
O6 C15 1.440(3) . ?
O6 H6E 0.866(18) . ?
N1 C8 1.299(2) . ?
N1 C9 1.432(2) . ?
O2 C2 1.368(3) . ?
O2 C7 1.420(3) . ?
O1 C1 1.319(2) . ?
O7 H7WA 0.844(17) . ?
O7 H7WB 0.834(17) . ?
C6 C1 1.405(3) . ?
C6 C5 1.419(3) . ?
C6 C8 1.434(3) . ?
C1 C2 1.421(3) . ?
C15 C16 1.489(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C14 C13 1.391(3) . ?
C14 C9 1.394(3) . ?
C9 C10 1.391(3) . ?
C8 H8 0.9300 . ?
C5 C4 1.361(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.397(3) . ?
C4 H4 0.9300 . ?
C3 C2 1.375(3) . ?
C3 H3 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 C11 1.382(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O3 169.37(7) . . ?
O1 Cu1 N1 93.20(6) . . ?
O3 Cu1 N1 93.10(6) . . ?
O1 Cu1 O6 85.41(6) . . ?
O3 Cu1 O6 88.03(6) . . ?
N1 Cu1 O6 177.79(6) . . ?
O5 S1 O4 115.15(12) . . ?
O5 S1 O3 111.53(10) . . ?
O4 S1 O3 111.49(10) . . ?
O5 S1 C14 108.02(10) . . ?
O4 S1 C14 106.26(10) . . ?
O3 S1 C14 103.51(10) . . ?
C15 O6 Cu1 125.41(13) . . ?
C15 O6 H6E 110(2) . . ?
Cu1 O6 H6E 110(2) . . ?
S1 O3 Cu1 119.86(9) . . ?
C8 N1 C9 115.71(16) . . ?
C8 N1 Cu1 121.83(14) . . ?
C9 N1 Cu1 122.46(12) . . ?
C2 O2 C7 118.03(19) . . ?
C1 O1 Cu1 124.47(12) . . ?
H7WA O7 H7WB 102(3) . . ?
C1 C6 C5 120.20(19) . . ?
C1 C6 C8 122.94(17) . . ?
C5 C6 C8 116.82(18) . . ?
O1 C1 C6 124.10(17) . . ?
O1 C1 C2 118.04(17) . . ?
C6 C1 C2 117.82(17) . . ?
O6 C15 C16 112.2(2) . . ?
O6 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
O6 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
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 . . ?
C13 C14 C9 120.51(19) . . ?
C13 C14 S1 119.78(17) . . ?
C9 C14 S1 119.71(15) . . ?
C10 C9 C14 118.78(19) . . ?
C10 C9 N1 120.78(18) . . ?
C14 C9 N1 120.43(17) . . ?
N1 C8 C6 127.13(18) . . ?
N1 C8 H8 116.4 . . ?
C6 C8 H8 116.4 . . ?
C4 C5 C6 120.3(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C4 C3 120.4(2) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C2 C3 C4 120.4(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O2 C2 C3 125.16(19) . . ?
O2 C2 C1 113.90(17) . . ?
C3 C2 C1 120.9(2) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C10 C9 120.3(2) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 119.9(2) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?

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
O5 S1 O3 Cu1 179.50(11) . . . . ?
O4 S1 O3 Cu1 49.24(14) . . . . ?
C14 S1 O3 Cu1 -64.59(13) . . . . ?
Cu1 O1 C1 C6 22.7(3) . . . . ?
Cu1 O1 C1 C2 -159.59(14) . . . . ?
C5 C6 C1 O1 177.72(19) . . . . ?
C8 C6 C1 O1 0.0(3) . . . . ?
C5 C6 C1 C2 0.0(3) . . . . ?
C8 C6 C1 C2 -177.69(18) . . . . ?
Cu1 O6 C15 C16 -177.20(18) . . . . ?
O5 S1 C14 C13 -10.0(2) . . . . ?
O4 S1 C14 C13 114.09(18) . . . . ?
O3 S1 C14 C13 -128.37(17) . . . . ?
O5 S1 C14 C9 171.17(17) . . . . ?
O4 S1 C14 C9 -64.75(18) . . . . ?
O3 S1 C14 C9 52.80(18) . . . . ?
C13 C14 C9 C10 1.3(3) . . . . ?
S1 C14 C9 C10 -179.83(16) . . . . ?
C13 C14 C9 N1 -178.32(18) . . . . ?
S1 C14 C9 N1 0.5(3) . . . . ?
C8 N1 C9 C10 -42.0(3) . . . . ?
Cu1 N1 C9 C10 137.51(17) . . . . ?
C8 N1 C9 C14 137.62(19) . . . . ?
Cu1 N1 C9 C14 -42.8(2) . . . . ?
C9 N1 C8 C6 175.47(18) . . . . ?
Cu1 N1 C8 C6 -4.1(3) . . . . ?
C1 C6 C8 N1 -9.8(3) . . . . ?
C5 C6 C8 N1 172.4(2) . . . . ?
C1 C6 C5 C4 0.6(3) . . . . ?
C8 C6 C5 C4 178.5(2) . . . . ?
C6 C5 C4 C3 -0.8(3) . . . . ?
C5 C4 C3 C2 0.2(4) . . . . ?
C7 O2 C2 C3 0.4(3) . . . . ?
C7 O2 C2 C1 179.2(2) . . . . ?
C4 C3 C2 O2 179.2(2) . . . . ?
C4 C3 C2 C1 0.4(3) . . . . ?
O1 C1 C2 O2 2.7(3) . . . . ?
C6 C1 C2 O2 -179.40(18) . . . . ?
O1 C1 C2 C3 -178.37(19) . . . . ?
C6 C1 C2 C3 -0.5(3) . . . . ?
C14 C9 C10 C11 -1.7(3) . . . . ?
N1 C9 C10 C11 178.0(2) . . . . ?
C9 C10 C11 C12 0.9(4) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C9 C14 C13 C12 -0.2(3) . . . . ?
S1 C14 C13 C12 -179.02(18) . . . . ?

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
O7 H7WB O1 0.834(17) 2.51(3) 3.009(3) 120(3) 1_544
O7 H7WB O2 0.834(17) 2.111(18) 2.940(3) 172(3) 1_544
O7 H7WA O4 0.844(17) 1.98(2) 2.791(3) 161(3) 3_666
O6 H6E O7 0.866(18) 1.789(18) 2.654(2) 176(3) 1_566
C3 H3 O4 0.93 2.64 3.468(3) 149.2 2_556
C8 H8 O5 0.93 2.52 3.403(3) 157.6 4_575

_refine_diff_density_max         0.507
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.094

_shelxl_version_number           2014-1

