# 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 2018

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

data_1b
_database_code_depnum_ccdc_archive 'CCDC 1828639'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cu N2 O6 S'
_chemical_formula_weight         508.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'

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

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

_cell_length_a                   22.663(4)
_cell_length_b                   10.1552(7)
_cell_length_c                   9.7130(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2235.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      22.763
_cell_measurement_theta_max      45.8

_exptl_crystal_description       Prism
_exptl_crystal_colour            Brown-Yellow
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.613
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_correction_T_min  0.5874
_exptl_absorpt_correction_T_max  0.7193
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MACH3 Enraf Nonius'
_diffrn_measurement_method       omega/2-theta
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2443
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_v_R_equivalents   0.0000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.901
_diffrn_reflns_theta_max         74.874
_diffrn_reflns_theta_full        67.680
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.530
_diffrn_reflns_point_group_measured_fraction_full 0.532
_reflns_number_total             2443
_reflns_number_gt                2254
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.3608P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2443
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0845
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.010
_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
O2W1 O 0.5630(4) 0.387(2) 0.6810(19) 0.074(4) Uani 0.66(6) 1 d . . P . .
O2W2 O 0.5655(10) 0.436(4) 0.613(7) 0.088(13) Uani 0.34(6) 1 d . . P . .
H2B H 0.588(3) 0.385(8) 0.642(11) 0.106 Uiso 1 1 d . U . . .
H2A H 0.533(2) 0.363(4) 0.624(6) 0.058(12) Uiso 1 1 d . . . . .
Cu Cu 0.66245(2) 0.62411(4) 0.86483(6) 0.04495(14) Uani 1 1 d . . . . .
S S 0.58972(4) 0.77605(9) 1.10115(10) 0.0526(2) Uani 1 1 d . . . . .
N1 N 0.74439(12) 0.6543(2) 0.9054(3) 0.0420(5) Uani 1 1 d . . . . .
O1 O 0.67678(11) 0.4902(3) 0.7334(3) 0.0537(6) Uani 1 1 d . . . . .
O2 O 0.67452(13) 0.3034(3) 0.5497(3) 0.0672(8) Uani 1 1 d . . . . .
O3 O 0.54519(12) 0.6886(3) 1.0429(4) 0.0667(8) Uani 1 1 d . . . . .
O4 O 0.59686(13) 0.7665(3) 1.2478(3) 0.0707(8) Uani 1 1 d . . . . .
O1W O 0.58121(12) 0.6211(3) 0.7979(4) 0.0685(9) Uani 1 1 d . . . . .
H1A H 0.5523 0.6338 0.8458 0.086(17) Uiso 1 1 d . . . . .
H1B H 0.5714 0.5461 0.7505 0.12(2) Uiso 1 1 d . . . . .
N2 N 0.64888(12) 0.7506(3) 1.0178(4) 0.0498(6) Uani 1 1 d . . . . .
C1 C 0.72779(14) 0.4494(3) 0.6910(4) 0.0459(7) Uani 1 1 d . . . . .
C2 C 0.72946(17) 0.3480(3) 0.5883(4) 0.0541(8) Uani 1 1 d . . . . .
C3 C 0.7815(2) 0.3026(4) 0.5363(5) 0.0674(11) Uani 1 1 d . . . . .
H3 H 0.7814 0.2366 0.4699 0.081 Uiso 1 1 calc R U . . .
C4 C 0.83504(19) 0.3552(5) 0.5827(7) 0.0739(13) Uani 1 1 d . . . . .
H4 H 0.8704 0.3250 0.5457 0.089 Uiso 1 1 calc R U . . .
C5 C 0.83574(16) 0.4498(4) 0.6812(6) 0.0634(10) Uani 1 1 d . . . . .
H5 H 0.8716 0.4836 0.7114 0.076 Uiso 1 1 calc R U . . .
C6 C 0.78260(14) 0.4976(3) 0.7384(4) 0.0478(7) Uani 1 1 d . . . . .
C7 C 0.6722(2) 0.2022(4) 0.4471(5) 0.0713(12) Uani 1 1 d . . . . .
H7A H 0.6946 0.1261 0.4770 0.086 Uiso 1 1 calc R U . . .
H7B H 0.6889 0.2339 0.3614 0.086 Uiso 1 1 calc R U . . .
C8 C 0.6093(3) 0.1656(7) 0.4270(8) 0.110(2) Uani 1 1 d . . . . .
H8A H 0.6069 0.0919 0.3654 0.165 Uiso 1 1 calc R U . . .
H8B H 0.5883 0.2390 0.3885 0.165 Uiso 1 1 calc R U . . .
H8C H 0.5922 0.1424 0.5140 0.165 Uiso 1 1 calc R U . . .
C9 C 0.78734(14) 0.5951(3) 0.8427(4) 0.0484(8) Uani 1 1 d . . . . .
H9 H 0.8253 0.6190 0.8688 0.058 Uiso 1 1 calc R U . . .
C10 C 0.75384(15) 0.7526(3) 1.0073(4) 0.0439(6) Uani 1 1 d . . . . .
C11 C 0.80918(16) 0.7989(4) 1.0468(4) 0.0544(8) Uani 1 1 d . . . . .
H11 H 0.8429 0.7651 1.0054 0.065 Uiso 1 1 calc R U . . .
C12 C 0.81413(19) 0.8940(4) 1.1463(5) 0.0623(10) Uani 1 1 d . . . . .
H12 H 0.8512 0.9229 1.1741 0.075 Uiso 1 1 calc R U . . .
C13 C 0.76402(18) 0.9467(4) 1.2049(4) 0.0604(9) Uani 1 1 d . . . . .
H13 H 0.7675 1.0124 1.2711 0.073 Uiso 1 1 calc R U . . .
C14 C 0.70843(18) 0.9024(4) 1.1661(4) 0.0575(9) Uani 1 1 d . . . . .
H14 H 0.6749 0.9384 1.2067 0.069 Uiso 1 1 calc R U . . .
C15 C 0.70268(15) 0.8050(3) 1.0670(4) 0.0454(7) Uani 1 1 d . . . . .
C16 C 0.56598(16) 0.9378(4) 1.0643(4) 0.0541(8) Uani 1 1 d . . . . .
C17 C 0.52433(19) 0.9939(5) 1.1520(5) 0.0701(11) Uani 1 1 d . . . . .
H17 H 0.5115 0.9483 1.2294 0.084 Uiso 1 1 calc R U . . .
C18 C 0.5025(2) 1.1165(4) 1.1237(7) 0.0793(14) Uani 1 1 d . . . . .
H18 H 0.4739 1.1525 1.1811 0.095 Uiso 1 1 calc R U . . .
C19 C 0.52190(19) 1.1873(4) 1.0120(6) 0.0690(12) Uani 1 1 d . . . . .
C20 C 0.5644(2) 1.1321(4) 0.9267(5) 0.0701(11) Uani 1 1 d . . . . .
H20 H 0.5783 1.1791 0.8511 0.084 Uiso 1 1 calc R U . . .
C21 C 0.58626(19) 1.0067(4) 0.9537(5) 0.0631(10) Uani 1 1 d . . . . .
H21 H 0.6147 0.9700 0.8964 0.076 Uiso 1 1 calc R U . . .
C22 C 0.4994(3) 1.3263(5) 0.9852(8) 0.0942(18) Uani 1 1 d . . . . .
H22A H 0.4982 1.3421 0.8878 0.141 Uiso 1 1 calc R U . . .
H22B H 0.5253 1.3888 1.0279 0.141 Uiso 1 1 calc R U . . .
H22C H 0.4605 1.3355 1.0228 0.141 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
O2W1 O2W2 0.83(5) . ?
Cu O1 1.893(3) . ?
Cu N1 1.923(3) . ?
Cu O1W 1.953(3) . ?
Cu N2 1.988(3) . ?
S O4 1.437(3) . ?
S O3 1.458(3) . ?
S N2 1.588(3) . ?
S C16 1.765(4) . ?
N1 C9 1.296(4) . ?
N1 C10 1.421(4) . ?
O1 C1 1.295(4) . ?
O2 C2 1.377(5) . ?
O2 C7 1.433(5) . ?
N2 C15 1.421(4) . ?
C1 C6 1.412(4) . ?
C1 C2 1.434(5) . ?
C2 C3 1.363(5) . ?
C3 C4 1.400(6) . ?
C4 C5 1.356(7) . ?
C5 C6 1.413(5) . ?
C6 C9 1.421(5) . ?
C7 C8 1.484(7) . ?
C10 C11 1.393(5) . ?
C10 C15 1.402(5) . ?
C11 C12 1.371(6) . ?
C12 C13 1.379(6) . ?
C13 C14 1.390(6) . ?
C14 C15 1.387(5) . ?
C16 C21 1.362(6) . ?
C16 C17 1.394(5) . ?
C17 C18 1.367(6) . ?
C18 C19 1.374(8) . ?
C19 C20 1.389(7) . ?
C19 C22 1.523(6) . ?
C20 C21 1.392(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 Cu N1 95.00(11) . . ?
O1 Cu O1W 85.75(12) . . ?
N1 Cu O1W 168.88(14) . . ?
O1 Cu N2 174.04(14) . . ?
N1 Cu N2 83.86(12) . . ?
O1W Cu N2 96.50(12) . . ?
O4 S O3 114.9(2) . . ?
O4 S N2 113.56(19) . . ?
O3 S N2 106.71(17) . . ?
O4 S C16 107.4(2) . . ?
O3 S C16 106.07(18) . . ?
N2 S C16 107.79(17) . . ?
C9 N1 C10 122.6(3) . . ?
C9 N1 Cu 123.7(2) . . ?
C10 N1 Cu 113.6(2) . . ?
C1 O1 Cu 126.7(2) . . ?
C2 O2 C7 117.3(3) . . ?
C15 N2 S 119.3(3) . . ?
C15 N2 Cu 111.7(2) . . ?
S N2 Cu 128.11(18) . . ?
O1 C1 C6 124.8(3) . . ?
O1 C1 C2 118.3(3) . . ?
C6 C1 C2 116.9(3) . . ?
C3 C2 O2 124.8(4) . . ?
C3 C2 C1 121.6(3) . . ?
O2 C2 C1 113.7(3) . . ?
C2 C3 C4 120.1(4) . . ?
C5 C4 C3 120.5(4) . . ?
C4 C5 C6 120.7(4) . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 C9 122.7(3) . . ?
C5 C6 C9 117.1(3) . . ?
O2 C7 C8 107.9(4) . . ?
N1 C9 C6 127.0(3) . . ?
C11 C10 C15 120.2(3) . . ?
C11 C10 N1 124.4(3) . . ?
C15 C10 N1 115.5(3) . . ?
C12 C11 C10 120.4(4) . . ?
C11 C12 C13 119.8(4) . . ?
C12 C13 C14 120.6(4) . . ?
C15 C14 C13 120.3(4) . . ?
C14 C15 C10 118.7(3) . . ?
C14 C15 N2 126.3(3) . . ?
C10 C15 N2 115.0(3) . . ?
C21 C16 C17 120.0(4) . . ?
C21 C16 S 122.4(3) . . ?
C17 C16 S 117.6(3) . . ?
C18 C17 C16 119.6(5) . . ?
C17 C18 C19 121.3(5) . . ?
C18 C19 C20 118.8(4) . . ?
C18 C19 C22 120.9(5) . . ?
C20 C19 C22 120.3(6) . . ?
C19 C20 C21 120.3(5) . . ?
C16 C21 C20 119.9(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 Cu O1 C1 -3.2(3) . . . . ?
O1W Cu O1 C1 165.6(3) . . . . ?
O4 S N2 C15 -41.4(3) . . . . ?
O3 S N2 C15 -169.0(3) . . . . ?
C16 S N2 C15 77.4(3) . . . . ?
O4 S N2 Cu 126.9(3) . . . . ?
O3 S N2 Cu -0.7(3) . . . . ?
C16 S N2 Cu -114.3(2) . . . . ?
Cu O1 C1 C6 1.1(5) . . . . ?
Cu O1 C1 C2 -178.8(3) . . . . ?
C7 O2 C2 C3 -0.2(6) . . . . ?
C7 O2 C2 C1 179.8(4) . . . . ?
O1 C1 C2 C3 178.3(4) . . . . ?
C6 C1 C2 C3 -1.7(6) . . . . ?
O1 C1 C2 O2 -1.7(5) . . . . ?
C6 C1 C2 O2 178.3(3) . . . . ?
O2 C2 C3 C4 179.9(5) . . . . ?
C1 C2 C3 C4 -0.1(7) . . . . ?
C2 C3 C4 C5 1.2(8) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
O1 C1 C6 C5 -177.5(4) . . . . ?
C2 C1 C6 C5 2.5(5) . . . . ?
O1 C1 C6 C9 2.0(6) . . . . ?
C2 C1 C6 C9 -178.1(3) . . . . ?
C4 C5 C6 C1 -1.6(7) . . . . ?
C4 C5 C6 C9 179.0(4) . . . . ?
C2 O2 C7 C8 177.4(5) . . . . ?
C10 N1 C9 C6 -178.9(3) . . . . ?
Cu N1 C9 C6 -1.8(5) . . . . ?
C1 C6 C9 N1 -1.6(6) . . . . ?
C5 C6 C9 N1 177.9(4) . . . . ?
C9 N1 C10 C11 2.4(5) . . . . ?
Cu N1 C10 C11 -175.0(3) . . . . ?
C9 N1 C10 C15 -178.8(3) . . . . ?
Cu N1 C10 C15 3.8(4) . . . . ?
C15 C10 C11 C12 1.4(6) . . . . ?
N1 C10 C11 C12 -179.9(4) . . . . ?
C10 C11 C12 C13 -1.8(6) . . . . ?
C11 C12 C13 C14 1.3(7) . . . . ?
C12 C13 C14 C15 -0.3(6) . . . . ?
C13 C14 C15 C10 -0.1(6) . . . . ?
C13 C14 C15 N2 179.9(4) . . . . ?
C11 C10 C15 C14 -0.4(5) . . . . ?
N1 C10 C15 C14 -179.2(3) . . . . ?
C11 C10 C15 N2 179.6(3) . . . . ?
N1 C10 C15 N2 0.7(4) . . . . ?
S N2 C15 C14 -14.6(5) . . . . ?
Cu N2 C15 C14 175.3(3) . . . . ?
S N2 C15 C10 165.4(3) . . . . ?
Cu N2 C15 C10 -4.7(4) . . . . ?
O4 S C16 C21 140.1(3) . . . . ?
O3 S C16 C21 -96.6(4) . . . . ?
N2 S C16 C21 17.4(4) . . . . ?
O4 S C16 C17 -40.8(4) . . . . ?
O3 S C16 C17 82.5(4) . . . . ?
N2 S C16 C17 -163.5(3) . . . . ?
C21 C16 C17 C18 2.3(7) . . . . ?
S C16 C17 C18 -176.8(4) . . . . ?
C16 C17 C18 C19 -1.7(8) . . . . ?
C17 C18 C19 C20 0.3(8) . . . . ?
C17 C18 C19 C22 -177.1(5) . . . . ?
C18 C19 C20 C21 0.6(7) . . . . ?
C22 C19 C20 C21 178.0(4) . . . . ?
C17 C16 C21 C20 -1.5(6) . . . . ?
S C16 C21 C20 177.6(4) . . . . ?
C19 C20 C21 C16 0.0(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1A O3 0.814(3) 2.001(3) 2.608(5) 131.0(2) .
O1W H1B O2W1 0.917(3) 1.763(15) 2.668(13) 168.6(8) .
O1W H1B O2W2 0.917(3) 1.75(3) 2.62(2) 159(2) .
O2W1 H2A O3 0.90(5) 2.02(5) 2.898(10) 165(5) 2_664
O2W2 H2A O3 1.04(6) 2.02(5) 2.89(2) 140(5) 2_664

_refine_diff_density_max         0.179
_refine_diff_density_min         -0.594
_refine_diff_density_rms         0.056

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_md
_database_code_depnum_ccdc_archive 'CCDC 1828645'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H26 Cu N4 O3 S'
_chemical_formula_weight         634.19

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                   10.0829(18)
_cell_length_b                   16.324(3)
_cell_length_c                   16.992(3)
_cell_angle_alpha                90
_cell_angle_beta                 97.003(3)
_cell_angle_gamma                90
_cell_volume                     2775.9(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1365
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.03

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             1308
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.907
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6117
_exptl_absorpt_correction_T_max  0.8614
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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_reflns_number            24540
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.736
_diffrn_reflns_theta_max         27.145
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6118
_reflns_number_gt                4682
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+2.9940P] 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         6118
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0781
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
Cu Cu 0.89485(3) 0.78792(2) 0.06019(2) 0.01372(8) Uani 1 1 d . . . . .
S1 S 0.66836(6) 0.87559(4) 0.13667(3) 0.01540(13) Uani 1 1 d . . . . .
O11 O 0.55949(17) 0.93374(10) 0.12795(10) 0.0206(4) Uani 1 1 d . . . . .
O12 O 0.77720(17) 0.89201(10) 0.19787(10) 0.0198(4) Uani 1 1 d . . . . .
O13 O 1.00671(16) 0.69804(10) 0.10135(10) 0.0175(4) Uani 1 1 d . . . . .
N11 N 0.73182(19) 0.86288(12) 0.05571(11) 0.0147(4) Uani 1 1 d . . . . .
N12 N 0.76573(19) 0.71255(12) 0.00643(11) 0.0144(4) Uani 1 1 d . . . . .
C11 C 0.5994(2) 0.77942(14) 0.15759(13) 0.0150(5) Uani 1 1 d . . . . .
C12 C 0.6836(2) 0.71754(15) 0.19070(14) 0.0183(5) Uani 1 1 d . . . . .
H12 H 0.7744 0.7293 0.2089 0.022 Uiso 1 1 calc R U . . .
C13 C 0.6350(2) 0.63915(15) 0.19712(14) 0.0188(5) Uani 1 1 d . . . . .
H13 H 0.6932 0.5974 0.2198 0.023 Uiso 1 1 calc R U . . .
C14 C 0.5021(2) 0.62004(15) 0.17097(14) 0.0183(5) Uani 1 1 d . . . . .
C15 C 0.4188(3) 0.68322(15) 0.13929(14) 0.0198(5) Uani 1 1 d . . . . .
H15 H 0.3274 0.6719 0.1222 0.024 Uiso 1 1 calc R U . . .
C16 C 0.4667(2) 0.76207(15) 0.13220(14) 0.0180(5) Uani 1 1 d . . . . .
H16 H 0.4086 0.8041 0.1100 0.022 Uiso 1 1 calc R U . . .
C17 C 0.4515(3) 0.53360(15) 0.17716(15) 0.0231(6) Uani 1 1 d . . . . .
H17A H 0.5211 0.4949 0.1659 0.035 Uiso 1 1 calc R U . . .
H17B H 0.3719 0.5257 0.1387 0.035 Uiso 1 1 calc R U . . .
H17C H 0.4288 0.5241 0.2308 0.035 Uiso 1 1 calc R U . . .
C18 C 0.6404(2) 0.83569(14) -0.01050(13) 0.0151(5) Uani 1 1 d . . . . .
C19 C 0.5388(2) 0.88329(15) -0.05022(14) 0.0191(5) Uani 1 1 d . . . . .
H19 H 0.5231 0.9370 -0.0319 0.023 Uiso 1 1 calc R U . . .
C110 C 0.4604(2) 0.85252(16) -0.11637(15) 0.0212(5) Uani 1 1 d . . . . .
H110 H 0.3907 0.8852 -0.1428 0.025 Uiso 1 1 calc R U . . .
C111 C 0.4828(2) 0.77471(16) -0.14428(14) 0.0215(5) Uani 1 1 d . . . . .
H111 H 0.4288 0.7544 -0.1898 0.026 Uiso 1 1 calc R U . . .
C112 C 0.5835(2) 0.72644(15) -0.10596(14) 0.0177(5) Uani 1 1 d . . . . .
H112 H 0.6004 0.6735 -0.1258 0.021 Uiso 1 1 calc R U . . .
C113 C 0.6598(2) 0.75591(15) -0.03815(14) 0.0150(5) Uani 1 1 d . . . . .
C114 C 0.7609(2) 0.63344(14) 0.01514(13) 0.0156(5) Uani 1 1 d . . . . .
H114 H 0.6846 0.6058 -0.0104 0.019 Uiso 1 1 calc R U . . .
C115 C 0.8605(2) 0.58488(14) 0.05967(13) 0.0143(5) Uani 1 1 d . . . . .
C116 C 0.8403(2) 0.49678(14) 0.06523(13) 0.0162(5) Uani 1 1 d . . . . .
C117 C 0.7180(3) 0.45715(15) 0.04042(14) 0.0199(5) Uani 1 1 d . . . . .
H117 H 0.6429 0.4890 0.0197 0.024 Uiso 1 1 calc R U . . .
C118 C 0.7047(3) 0.37352(15) 0.04549(15) 0.0224(6) Uani 1 1 d . . . . .
H118 H 0.6207 0.3488 0.0286 0.027 Uiso 1 1 calc R U . . .
C119 C 0.8126(3) 0.32448(16) 0.07499(16) 0.0256(6) Uani 1 1 d . . . . .
H119 H 0.8035 0.2666 0.0766 0.031 Uiso 1 1 calc R U . . .
C120 C 0.9319(3) 0.36097(15) 0.10169(15) 0.0233(6) Uani 1 1 d . . . . .
H120 H 1.0055 0.3279 0.1224 0.028 Uiso 1 1 calc R U . . .
C121 C 0.9475(2) 0.44674(15) 0.09910(14) 0.0175(5) Uani 1 1 d . . . . .
C122 C 1.0684(2) 0.48439(15) 0.13285(14) 0.0188(5) Uani 1 1 d . . . . .
H122 H 1.1405 0.4511 0.1553 0.023 Uiso 1 1 calc R U . . .
C123 C 1.0825(2) 0.56683(15) 0.13353(14) 0.0172(5) Uani 1 1 d . . . . .
H123 H 1.1628 0.5900 0.1592 0.021 Uiso 1 1 calc R U . . .
C124 C 0.9803(2) 0.62059(14) 0.09677(13) 0.0144(5) Uani 1 1 d . . . . .
N21 N 1.04091(19) 0.86323(11) 0.10816(11) 0.0144(4) Uani 1 1 d . . . . .
N22 N 0.96544(19) 0.84528(12) -0.04769(11) 0.0147(4) Uani 1 1 d . . . . .
C21 C 1.0821(2) 0.86467(15) 0.18619(14) 0.0187(5) Uani 1 1 d . . . . .
H21 H 1.0331 0.8346 0.2208 0.022 Uiso 1 1 calc R U . . .
C22 C 1.1935(2) 0.90844(16) 0.21828(15) 0.0206(5) Uani 1 1 d . . . . .
H22 H 1.2204 0.9083 0.2738 0.025 Uiso 1 1 calc R U . . .
C23 C 1.2644(2) 0.95205(16) 0.16819(15) 0.0215(5) Uani 1 1 d . . . . .
H23 H 1.3413 0.9824 0.1887 0.026 Uiso 1 1 calc R U . . .
C24 C 1.2224(2) 0.95121(15) 0.08757(15) 0.0197(5) Uani 1 1 d . . . . .
H24 H 1.2700 0.9813 0.0522 0.024 Uiso 1 1 calc R U . . .
C25 C 1.1106(2) 0.90616(14) 0.05877(14) 0.0148(5) Uani 1 1 d . . . . .
C26 C 1.0630(2) 0.90016(13) -0.02719(14) 0.0140(5) Uani 1 1 d . . . . .
C27 C 1.1161(2) 0.94815(15) -0.08315(14) 0.0192(5) Uani 1 1 d . . . . .
H27 H 1.1830 0.9877 -0.0671 0.023 Uiso 1 1 calc R U . . .
C28 C 1.0704(2) 0.93768(15) -0.16247(15) 0.0205(5) Uani 1 1 d . . . . .
H28 H 1.1062 0.9693 -0.2018 0.025 Uiso 1 1 calc R U . . .
C29 C 0.9716(2) 0.88041(15) -0.18374(14) 0.0187(5) Uani 1 1 d . . . . .
H29 H 0.9393 0.8713 -0.2379 0.022 Uiso 1 1 calc R U . . .
C210 C 0.9206(2) 0.83660(15) -0.12461(14) 0.0171(5) Uani 1 1 d . . . . .
H210 H 0.8505 0.7986 -0.1393 0.021 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
Cu O13 1.9292(16) . ?
Cu N12 1.9373(19) . ?
Cu N21 2.0130(19) . ?
Cu N11 2.043(2) . ?
Cu N22 2.2499(19) . ?
S1 O12 1.4420(17) . ?
S1 O11 1.4451(17) . ?
S1 N11 1.600(2) . ?
S1 C11 1.770(2) . ?
O13 C124 1.292(3) . ?
N11 C18 1.435(3) . ?
N12 C114 1.301(3) . ?
N12 C113 1.421(3) . ?
C11 C16 1.384(3) . ?
C11 C12 1.393(3) . ?
C12 C13 1.379(3) . ?
C13 C14 1.395(3) . ?
C14 C15 1.396(3) . ?
C14 C17 1.508(3) . ?
C15 C16 1.385(3) . ?
C18 C19 1.393(3) . ?
C18 C113 1.406(3) . ?
C19 C110 1.387(3) . ?
C110 C111 1.384(4) . ?
C111 C112 1.384(3) . ?
C112 C113 1.391(3) . ?
C114 C115 1.422(3) . ?
C115 C124 1.419(3) . ?
C115 C116 1.457(3) . ?
C116 C117 1.411(3) . ?
C116 C121 1.419(3) . ?
C117 C118 1.375(3) . ?
C118 C119 1.394(4) . ?
C119 C120 1.369(4) . ?
C120 C121 1.410(3) . ?
C121 C122 1.422(3) . ?
C122 C123 1.353(3) . ?
C123 C124 1.437(3) . ?
N21 C21 1.340(3) . ?
N21 C25 1.354(3) . ?
N22 C210 1.337(3) . ?
N22 C26 1.344(3) . ?
C21 C22 1.386(3) . ?
C22 C23 1.375(4) . ?
C23 C24 1.383(3) . ?
C24 C25 1.385(3) . ?
C25 C26 1.484(3) . ?
C26 C27 1.389(3) . ?
C27 C28 1.381(3) . ?
C28 C29 1.382(3) . ?
C29 C210 1.382(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
O13 Cu N12 91.01(8) . . ?
O13 Cu N21 87.20(7) . . ?
N12 Cu N21 174.40(8) . . ?
O13 Cu N11 154.31(7) . . ?
N12 Cu N11 82.61(8) . . ?
N21 Cu N11 101.23(8) . . ?
O13 Cu N22 112.51(7) . . ?
N12 Cu N22 98.12(8) . . ?
N21 Cu N22 77.71(7) . . ?
N11 Cu N22 93.06(7) . . ?
O12 S1 O11 116.97(10) . . ?
O12 S1 N11 107.17(10) . . ?
O11 S1 N11 112.05(10) . . ?
O12 S1 C11 107.64(11) . . ?
O11 S1 C11 106.93(11) . . ?
N11 S1 C11 105.40(10) . . ?
C124 O13 Cu 127.98(15) . . ?
C18 N11 S1 115.37(15) . . ?
C18 N11 Cu 106.30(14) . . ?
S1 N11 Cu 116.73(11) . . ?
C114 N12 C113 121.3(2) . . ?
C114 N12 Cu 127.50(17) . . ?
C113 N12 Cu 110.69(15) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 S1 120.47(18) . . ?
C12 C11 S1 119.31(18) . . ?
C13 C12 C11 120.0(2) . . ?
C12 C13 C14 121.3(2) . . ?
C13 C14 C15 117.9(2) . . ?
C13 C14 C17 120.5(2) . . ?
C15 C14 C17 121.7(2) . . ?
C16 C15 C14 121.3(2) . . ?
C11 C16 C15 119.8(2) . . ?
C19 C18 C113 118.6(2) . . ?
C19 C18 N11 124.9(2) . . ?
C113 C18 N11 116.5(2) . . ?
C110 C19 C18 120.2(2) . . ?
C111 C110 C19 120.6(2) . . ?
C110 C111 C112 120.2(2) . . ?
C111 C112 C113 119.5(2) . . ?
C112 C113 C18 120.8(2) . . ?
C112 C113 N12 125.0(2) . . ?
C18 C113 N12 114.2(2) . . ?
N12 C114 C115 125.4(2) . . ?
C124 C115 C114 121.0(2) . . ?
C124 C115 C116 119.6(2) . . ?
C114 C115 C116 119.3(2) . . ?
C117 C116 C121 116.9(2) . . ?
C117 C116 C115 123.8(2) . . ?
C121 C116 C115 119.3(2) . . ?
C118 C117 C116 121.6(2) . . ?
C117 C118 C119 121.0(2) . . ?
C120 C119 C118 119.0(2) . . ?
C119 C120 C121 121.2(2) . . ?
C120 C121 C116 120.1(2) . . ?
C120 C121 C122 120.7(2) . . ?
C116 C121 C122 119.2(2) . . ?
C123 C122 C121 121.2(2) . . ?
C122 C123 C124 122.3(2) . . ?
O13 C124 C115 125.9(2) . . ?
O13 C124 C123 116.1(2) . . ?
C115 C124 C123 118.0(2) . . ?
C21 N21 C25 118.8(2) . . ?
C21 N21 Cu 122.30(16) . . ?
C25 N21 Cu 118.33(15) . . ?
C210 N22 C26 118.3(2) . . ?
C210 N22 Cu 130.49(16) . . ?
C26 N22 Cu 111.11(15) . . ?
N21 C21 C22 122.5(2) . . ?
C23 C22 C21 118.7(2) . . ?
C22 C23 C24 119.2(2) . . ?
C23 C24 C25 119.5(2) . . ?
N21 C25 C24 121.2(2) . . ?
N21 C25 C26 116.5(2) . . ?
C24 C25 C26 122.3(2) . . ?
N22 C26 C27 122.0(2) . . ?
N22 C26 C25 116.0(2) . . ?
C27 C26 C25 122.1(2) . . ?
C28 C27 C26 119.2(2) . . ?
C27 C28 C29 118.9(2) . . ?
C28 C29 C210 118.7(2) . . ?
N22 C210 C29 123.0(2) . . ?

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
C23 H23 O11 0.95 2.66 3.147(3) 112.2 1_655
C27 H27 N11 0.95 2.59 3.451(3) 151.7 3_775
C28 H28 O12 0.95 2.55 3.268(3) 132.8 3_775
C122 H122 O12 0.95 2.71 3.447(3) 135.0 4_756

_refine_diff_density_max         0.489
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.076

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_1a_CuP-1
_database_code_depnum_ccdc_archive 'CCDC 1828642'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H24 Cu N2 O6 S'
_chemical_formula_weight         508.03

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                   5.754(2)
_cell_length_b                   9.595(3)
_cell_length_c                   19.723(7)
_cell_angle_alpha                90.663(6)
_cell_angle_beta                 91.571(6)
_cell_angle_gamma                100.876(6)
_cell_volume                     1068.8(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)

_cell_measurement_reflns_used    1268
_cell_measurement_theta_min      2.9655
_cell_measurement_theta_max      28.3735

_exptl_crystal_description       Plate
_exptl_crystal_colour            'Green olive'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.08

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_F_000             526
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.163
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.796372
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
Sheldrick, G. M. SADABS, An empirical absorption correction 
program for area detector data. 
University of Gottingen, Germany, 1996 
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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  'Smart-CCD-1000 BRUKER'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19778
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.162
_diffrn_reflns_theta_max         28.444
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5307
_reflns_number_gt                4047
_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 Smart'
_computing_cell_refinement       'BRUKER Smart'
_computing_data_reduction        'BRUKER Smart'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0385P)²+0.4957P] 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         5307
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0532
_refine_ls_R_factor_gt           0.0344
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0813
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
O2W1 O 0.967(3) 0.4379(11) 0.4390(8) 0.057(3) Uiso 0.43(4) 1 d . . P . .
O2W2 O 1.0187(18) 0.4576(8) 0.4226(6) 0.058(2) Uiso 0.57(4) 1 d . . P . .
H2W1 H 1.027(11) 0.363(6) 0.431(3) 0.18(2) Uiso 1 1 d . . . . .
H2W2 H 0.883(4) 0.394(3) 0.4655(13) 0.035(7) Uiso 1 1 d . . . . .
Cu Cu 0.55207(5) 0.24116(3) 0.30258(2) 0.03608(9) Uani 1 1 d . . . . .
S S 0.17856(10) 0.42803(6) 0.24237(3) 0.03786(14) Uani 1 1 d . . . . .
O1W O 0.5693(5) 0.3928(2) 0.36919(11) 0.0612(6) Uani 1 1 d . . . . .
H1W1 H 0.526(8) 0.460(5) 0.353(2) 0.115(16) Uiso 1 1 d . . . . .
H1W2 H 0.684(8) 0.428(4) 0.383(2) 0.104(17) Uiso 1 1 d . . . . .
O1 O 0.7897(3) 0.18479(16) 0.35895(8) 0.0406(4) Uani 1 1 d . . . . .
O2 O 1.1378(3) 0.16639(17) 0.44304(9) 0.0483(4) Uani 1 1 d . . . . .
O4 O -0.0757(3) 0.40387(19) 0.23766(9) 0.0500(4) Uani 1 1 d . . . . .
O3 O 0.2881(3) 0.51900(18) 0.29774(8) 0.0537(5) Uani 1 1 d . . . . .
N1 N 0.5197(3) 0.07752(18) 0.24346(9) 0.0335(4) Uani 1 1 d . . . . .
N2 N 0.2849(3) 0.28595(18) 0.24471(9) 0.0352(4) Uani 1 1 d . . . . .
C1 C 0.8906(4) 0.0751(2) 0.35052(11) 0.0337(4) Uani 1 1 d . . . . .
C2 C 1.0816(4) 0.0604(2) 0.39512(12) 0.0389(5) Uani 1 1 d . . . . .
C3 C 1.1937(5) -0.0533(3) 0.38916(13) 0.0485(6) Uani 1 1 d . . . . .
H3 H 1.3186 -0.0611 0.4189 0.058 Uiso 1 1 calc R U . . .
C4 C 1.1221(5) -0.1575(3) 0.33884(14) 0.0525(6) Uani 1 1 d . . . . .
H4 H 1.1998 -0.2338 0.3350 0.063 Uiso 1 1 calc R U . . .
C5 C 0.9395(5) -0.1472(2) 0.29568(13) 0.0477(6) Uani 1 1 d . . . . .
H5 H 0.8907 -0.2177 0.2628 0.057 Uiso 1 1 calc R U . . .
C6 C 0.8207(4) -0.0300(2) 0.29986(11) 0.0370(5) Uani 1 1 d . . . . .
C7 C 1.3315(4) 0.1596(3) 0.48941(13) 0.0475(6) Uani 1 1 d . . . . .
H7A H 1.4749 0.1592 0.4647 0.057 Uiso 1 1 calc R U . . .
H7B H 1.2979 0.0734 0.5155 0.057 Uiso 1 1 calc R U . . .
C8 C 1.3632(5) 0.2865(3) 0.53554(15) 0.0615(7) Uani 1 1 d . . . . .
H8A H 1.4002 0.3711 0.5094 0.092 Uiso 1 1 calc R U . . .
H8B H 1.4901 0.2834 0.5678 0.092 Uiso 1 1 calc R U . . .
H8C H 1.2195 0.2867 0.5592 0.092 Uiso 1 1 calc R U . . .
C9 C 0.6380(4) -0.0244(2) 0.25095(11) 0.0386(5) Uani 1 1 d . . . . .
H9 H 0.5986 -0.1016 0.2211 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3394(4) 0.0697(2) 0.19235(11) 0.0345(4) Uani 1 1 d . . . . .
C11 C 0.2859(4) -0.0368(2) 0.14324(12) 0.0448(6) Uani 1 1 d . . . . .
H11 H 0.3759 -0.1076 0.1415 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1018(5) -0.0392(3) 0.09713(13) 0.0492(6) Uani 1 1 d . . . . .
H12 H 0.0685 -0.1106 0.0640 0.059 Uiso 1 1 calc R U . . .
C13 C -0.0327(4) 0.0647(3) 0.10037(13) 0.0472(6) Uani 1 1 d . . . . .
H13 H -0.1596 0.0622 0.0699 0.057 Uiso 1 1 calc R U . . .
C14 C 0.0184(4) 0.1725(2) 0.14825(12) 0.0411(5) Uani 1 1 d . . . . .
H14 H -0.0753 0.2415 0.1499 0.049 Uiso 1 1 calc R U . . .
C15 C 0.2087(4) 0.1798(2) 0.19439(10) 0.0338(4) Uani 1 1 d . . . . .
C16 C 0.2795(4) 0.5164(2) 0.16748(11) 0.0348(5) Uani 1 1 d . . . . .
C17 C 0.1261(4) 0.5301(2) 0.11434(12) 0.0416(5) Uani 1 1 d . . . . .
H17 H -0.0339 0.4905 0.1170 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2086(4) 0.6025(2) 0.05696(12) 0.0444(5) Uani 1 1 d . . . . .
H18 H 0.1026 0.6115 0.0215 0.053 Uiso 1 1 calc R U . . .
C19 C 0.4444(5) 0.6616(2) 0.05117(13) 0.0463(6) Uani 1 1 d . . . . .
C20 C 0.5955(4) 0.6472(3) 0.10543(15) 0.0535(7) Uani 1 1 d . . . . .
H20 H 0.7551 0.6876 0.1029 0.064 Uiso 1 1 calc R U . . .
C21 C 0.5174(4) 0.5752(2) 0.16293(14) 0.0470(6) Uani 1 1 d . . . . .
H21 H 0.6234 0.5662 0.1983 0.056 Uiso 1 1 calc R U . . .
C22 C 0.5318(6) 0.7393(3) -0.01150(16) 0.0708(9) Uani 1 1 d . . . . .
H22A H 0.5635 0.8396 -0.0022 0.106 Uiso 1 1 calc R U . . .
H22B H 0.4134 0.7177 -0.0473 0.106 Uiso 1 1 calc R U . . .
H22C H 0.6745 0.7102 -0.0252 0.106 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
Cu O1 1.8993(15) . ?
Cu N1 1.9222(18) . ?
Cu O1W 1.935(2) . ?
Cu N2 2.0035(18) . ?
Cu O4 2.7566(18) 1_655 ?
S O4 1.4378(18) . ?
S O3 1.4437(17) . ?
S N2 1.5969(18) . ?
S C16 1.769(2) . ?
O1 C1 1.305(2) . ?
O2 C2 1.367(3) . ?
O2 C7 1.434(3) . ?
N1 C9 1.300(3) . ?
N1 C10 1.418(3) . ?
N2 C15 1.414(3) . ?
C1 C6 1.407(3) . ?
C1 C2 1.418(3) . ?
C2 C3 1.374(3) . ?
C3 C4 1.398(3) . ?
C4 C5 1.353(3) . ?
C5 C6 1.424(3) . ?
C6 C9 1.416(3) . ?
C7 C8 1.492(4) . ?
C10 C11 1.385(3) . ?
C10 C15 1.408(3) . ?
C11 C12 1.373(3) . ?
C12 C13 1.375(4) . ?
C13 C14 1.377(3) . ?
C14 C15 1.395(3) . ?
C16 C17 1.375(3) . ?
C16 C21 1.385(3) . ?
C17 C18 1.383(3) . ?
C18 C19 1.377(4) . ?
C19 C20 1.385(4) . ?
C19 C22 1.500(4) . ?
C20 C21 1.376(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu N1 93.97(7) . . ?
O1 Cu O1W 84.04(8) . . ?
N1 Cu O1W 174.06(9) . . ?
O1 Cu N2 175.48(7) . . ?
N1 Cu N2 83.57(7) . . ?
O1W Cu N2 98.03(9) . . ?
O1 Cu O4 85.28(7) . 1_655 ?
N1 Cu O4 96.59(7) . 1_655 ?
O1W Cu O4 88.84(9) . 1_655 ?
N2 Cu O4 98.75(7) . 1_655 ?
O4 S O3 115.95(11) . . ?
O4 S N2 113.93(10) . . ?
O3 S N2 107.54(10) . . ?
O4 S C16 106.23(10) . . ?
O3 S C16 105.70(11) . . ?
N2 S C16 106.81(10) . . ?
C1 O1 Cu 127.52(14) . . ?
C2 O2 C7 117.35(18) . . ?
C9 N1 C10 121.10(18) . . ?
C9 N1 Cu 124.51(15) . . ?
C10 N1 Cu 114.22(13) . . ?
C15 N2 S 118.60(14) . . ?
C15 N2 Cu 111.66(13) . . ?
S N2 Cu 129.19(10) . . ?
O1 C1 C6 123.92(19) . . ?
O1 C1 C2 118.27(19) . . ?
C6 C1 C2 117.82(19) . . ?
O2 C2 C3 124.8(2) . . ?
O2 C2 C1 114.20(19) . . ?
C3 C2 C1 121.0(2) . . ?
C2 C3 C4 120.7(2) . . ?
C5 C4 C3 119.8(2) . . ?
C4 C5 C6 121.0(2) . . ?
C1 C6 C9 123.0(2) . . ?
C1 C6 C5 119.6(2) . . ?
C9 C6 C5 117.3(2) . . ?
O2 C7 C8 107.9(2) . . ?
N1 C9 C6 126.7(2) . . ?
C11 C10 C15 120.1(2) . . ?
C11 C10 N1 124.7(2) . . ?
C15 C10 N1 115.19(18) . . ?
C12 C11 C10 121.0(2) . . ?
C11 C12 C13 119.4(2) . . ?
C12 C13 C14 120.7(2) . . ?
C13 C14 C15 121.0(2) . . ?
C14 C15 C10 117.7(2) . . ?
C14 C15 N2 127.0(2) . . ?
C10 C15 N2 115.27(18) . . ?
C17 C16 C21 119.5(2) . . ?
C17 C16 S 121.39(17) . . ?
C21 C16 S 119.15(18) . . ?
C16 C17 C18 120.3(2) . . ?
C19 C18 C17 121.4(2) . . ?
C18 C19 C20 117.4(2) . . ?
C18 C19 C22 120.8(3) . . ?
C20 C19 C22 121.8(2) . . ?
C21 C20 C19 122.2(2) . . ?
C20 C21 C16 119.3(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1W1 O3 0.81(5) 1.90(5) 2.593(3) 144(4) .
O1W H1W2 O2W1 0.73(4) 1.93(4) 2.601(8) 154(5) .
O1W H1W2 O2W2 0.73(4) 2.03(4) 2.723(7) 160(5) .

_refine_diff_density_max         0.324
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_3md
_database_code_depnum_ccdc_archive 'CCDC 1828641'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 Cu N3 O4 S'
_chemical_formula_weight         550.09

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                   9.1259(18)
_cell_length_b                   10.853(2)
_cell_length_c                   13.207(2)
_cell_angle_alpha                101.339(11)
_cell_angle_beta                 100.351(10)
_cell_angle_gamma                110.211(10)
_cell_volume                     1159.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1976
_cell_measurement_theta_min      2.26
_cell_measurement_theta_max      23.33

_exptl_crystal_description       Plate
_exptl_crystal_colour            green
_exptl_crystal_size_min          0.02
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_max          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.576
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    1.074
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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_reflns_number            20306
_diffrn_reflns_av_unetI/netI     0.0958
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.633
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4535
_reflns_number_gt                3128
_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-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0542P)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         4535
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0925
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1138
_refine_ls_wR_factor_gt          0.0999
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_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
Cu Cu 0.42320(5) 0.16064(5) 0.68722(4) 0.01415(16) Uani 1 1 d . . . . .
N11 N 0.2739(3) 0.0642(3) 0.5458(3) 0.0156(7) Uani 1 1 d . . . . .
N12 N 0.3129(3) 0.2897(3) 0.6882(2) 0.0148(7) Uani 1 1 d . . . . .
S S 0.22772(11) 0.30665(10) 0.78355(8) 0.0143(2) Uani 1 1 d . . . . .
O1 O 0.0551(3) 0.2249(3) 0.7488(2) 0.0179(6) Uani 1 1 d . . . . .
O2 O 0.3217(3) 0.2865(3) 0.8741(2) 0.0186(6) Uani 1 1 d . . . . .
O3 O 0.4752(3) 0.0103(3) 0.6982(2) 0.0194(6) Uani 1 1 d . . . . .
O4 O 0.6175(3) -0.1462(3) 0.7470(2) 0.0227(7) Uani 1 1 d . . . . .
C11 C 0.4398(4) -0.1016(4) 0.6227(3) 0.0161(9) Uani 1 1 d . . . . .
C12 C 0.5119(4) -0.1935(4) 0.6461(3) 0.0185(9) Uani 1 1 d . . . . .
C13 C 0.4774(5) -0.3148(4) 0.5719(3) 0.0219(10) Uani 1 1 d . . . . .
H13 H 0.5236 -0.3763 0.5901 0.026 Uiso 1 1 calc R U . . .
C14 C 0.3736(5) -0.3483(4) 0.4688(3) 0.0245(10) Uani 1 1 d . . . . .
H14 H 0.3517 -0.4312 0.4171 0.029 Uiso 1 1 calc R U . . .
C15 C 0.3051(4) -0.2610(4) 0.4439(3) 0.0189(9) Uani 1 1 d . . . . .
H15 H 0.2355 -0.2837 0.3742 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3354(4) -0.1369(4) 0.5199(3) 0.0158(9) Uani 1 1 d . . . . .
C17 C 0.7037(5) -0.2263(4) 0.7771(3) 0.0232(10) Uani 1 1 d . . . . .
H17A H 0.7539 -0.2523 0.7204 0.028 Uiso 1 1 calc R U . . .
H17B H 0.6293 -0.3108 0.7880 0.028 Uiso 1 1 calc R U . . .
C18 C 0.8319(5) -0.1403(5) 0.8794(4) 0.0316(11) Uani 1 1 d . . . . .
H18A H 0.9009 -0.0546 0.8687 0.047 Uiso 1 1 calc R U . . .
H18B H 0.8982 -0.1902 0.9004 0.047 Uiso 1 1 calc R U . . .
H18C H 0.7804 -0.1200 0.9360 0.047 Uiso 1 1 calc R U . . .
C19 C 0.2558(4) -0.0530(4) 0.4877(3) 0.0157(9) Uani 1 1 d . . . . .
H19 H 0.1837 -0.0861 0.4178 0.019 Uiso 1 1 calc R U . . .
C110 C 0.1860(4) 0.1401(4) 0.5077(3) 0.0137(8) Uani 1 1 d . . . . .
C111 C 0.0809(4) 0.1021(4) 0.4063(3) 0.0166(9) Uani 1 1 d . . . . .
H111 H 0.0600 0.0180 0.3564 0.020 Uiso 1 1 calc R U . . .
C112 C 0.0068(4) 0.1866(4) 0.3782(3) 0.0186(9) Uani 1 1 d . . . . .
H112 H -0.0696 0.1585 0.3103 0.022 Uiso 1 1 calc R U . . .
C113 C 0.0438(4) 0.3112(4) 0.4484(3) 0.0193(9) Uani 1 1 d . . . . .
H113 H -0.0030 0.3711 0.4275 0.023 Uiso 1 1 calc R U . . .
C114 C 0.1485(4) 0.3505(4) 0.5494(3) 0.0175(9) Uani 1 1 d . . . . .
H114 H 0.1754 0.4382 0.5964 0.021 Uiso 1 1 calc R U . . .
C115 C 0.2146(4) 0.2629(4) 0.5826(3) 0.0132(8) Uani 1 1 d . . . . .
C116 C 0.2479(4) 0.4794(4) 0.8220(3) 0.0150(9) Uani 1 1 d . . . . .
C117 C 0.1212(4) 0.5142(4) 0.7801(3) 0.0157(9) Uani 1 1 d . . . . .
H117 H 0.0234 0.4455 0.7324 0.019 Uiso 1 1 calc R U . . .
C118 C 0.1383(4) 0.6480(4) 0.8080(3) 0.0179(9) Uani 1 1 d . . . . .
H118 H 0.0515 0.6709 0.7787 0.021 Uiso 1 1 calc R U . . .
C119 C 0.2795(5) 0.7512(4) 0.8780(3) 0.0185(9) Uani 1 1 d . . . . .
C120 C 0.4028(4) 0.7135(4) 0.9219(3) 0.0186(9) Uani 1 1 d . . . . .
H120 H 0.4992 0.7817 0.9714 0.022 Uiso 1 1 calc R U . . .
C121 C 0.3881(4) 0.5799(4) 0.8953(3) 0.0163(9) Uani 1 1 d . . . . .
H121 H 0.4731 0.5564 0.9267 0.020 Uiso 1 1 calc R U . . .
C122 C 0.2984(5) 0.8978(4) 0.9066(4) 0.0249(10) Uani 1 1 d . . . . .
H12A H 0.3467 0.9390 0.9840 0.037 Uiso 1 1 calc R U . . .
H12B H 0.1919 0.9021 0.8867 0.037 Uiso 1 1 calc R U . . .
H12C H 0.3691 0.9481 0.8679 0.037 Uiso 1 1 calc R U . . .
N21 N 0.6294(3) 0.2817(3) 0.8037(3) 0.0156(7) Uani 1 1 d . . . . .
C21 C 0.7361(4) 0.2327(4) 0.8448(3) 0.0174(9) Uani 1 1 d . . . . .
H21 H 0.7111 0.1376 0.8204 0.021 Uiso 1 1 calc R U . . .
C22 C 0.8806(4) 0.3154(4) 0.9211(3) 0.0151(9) Uani 1 1 d . . . . .
H22 H 0.9522 0.2760 0.9477 0.018 Uiso 1 1 calc R U . . .
C23 C 0.9224(4) 0.4533(4) 0.9589(3) 0.0127(8) Uani 1 1 d . . . . .
C24 C 0.8092(4) 0.5030(4) 0.9169(3) 0.0168(9) Uani 1 1 d . . . . .
H24 H 0.8291 0.5971 0.9418 0.020 Uiso 1 1 calc R U . . .
C25 C 0.6698(4) 0.4154(4) 0.8400(3) 0.0167(9) Uani 1 1 d . . . . .
H25 H 0.5974 0.4525 0.8108 0.020 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
Cu O3 1.874(3) . ?
Cu N11 1.942(3) . ?
Cu N12 1.987(3) . ?
Cu N21 2.023(3) . ?
N11 C19 1.288(5) . ?
N11 C110 1.432(4) . ?
N12 C115 1.429(5) . ?
N12 S 1.607(3) . ?
S O2 1.441(3) . ?
S O1 1.447(3) . ?
S C116 1.777(4) . ?
O3 C11 1.307(4) . ?
O4 C12 1.377(5) . ?
O4 C17 1.425(4) . ?
C11 C16 1.406(5) . ?
C11 C12 1.423(5) . ?
C12 C13 1.374(6) . ?
C13 C14 1.409(6) . ?
C14 C15 1.362(5) . ?
C15 C16 1.417(5) . ?
C16 C19 1.428(5) . ?
C17 C18 1.499(6) . ?
C110 C111 1.389(5) . ?
C110 C115 1.404(5) . ?
C111 C112 1.381(5) . ?
C112 C113 1.372(6) . ?
C113 C114 1.381(5) . ?
C114 C115 1.389(5) . ?
C116 C121 1.392(5) . ?
C116 C117 1.393(5) . ?
C117 C118 1.372(5) . ?
C118 C119 1.391(5) . ?
C119 C120 1.395(5) . ?
C119 C122 1.502(5) . ?
C120 C121 1.375(5) . ?
N21 C25 1.328(5) . ?
N21 C21 1.344(4) . ?
C21 C22 1.382(5) . ?
C22 C23 1.370(5) . ?
C23 C24 1.401(5) . ?
C23 C23 1.494(7) 2_767 ?
C24 C25 1.369(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
O3 Cu N11 92.84(12) . . ?
O3 Cu N12 163.46(12) . . ?
N11 Cu N12 84.65(13) . . ?
O3 Cu N21 88.59(12) . . ?
N11 Cu N21 160.66(12) . . ?
N12 Cu N21 99.18(12) . . ?
C19 N11 C110 121.4(3) . . ?
C19 N11 Cu 125.8(3) . . ?
C110 N11 Cu 112.8(2) . . ?
C115 N12 S 115.9(2) . . ?
C115 N12 Cu 109.4(2) . . ?
S N12 Cu 115.57(17) . . ?
O2 S O1 117.51(16) . . ?
O2 S N12 106.84(15) . . ?
O1 S N12 112.07(16) . . ?
O2 S C116 106.37(17) . . ?
O1 S C116 105.64(16) . . ?
N12 S C116 107.93(17) . . ?
C11 O3 Cu 128.0(2) . . ?
C12 O4 C17 118.0(3) . . ?
O3 C11 C16 124.3(3) . . ?
O3 C11 C12 117.9(3) . . ?
C16 C11 C12 117.8(4) . . ?
C13 C12 O4 125.7(3) . . ?
C13 C12 C11 121.3(4) . . ?
O4 C12 C11 113.0(3) . . ?
C12 C13 C14 120.2(4) . . ?
C15 C14 C13 119.6(4) . . ?
C14 C15 C16 121.2(4) . . ?
C11 C16 C15 119.8(3) . . ?
C11 C16 C19 122.7(4) . . ?
C15 C16 C19 117.5(3) . . ?
O4 C17 C18 107.1(3) . . ?
N11 C19 C16 125.3(4) . . ?
C111 C110 C115 120.2(3) . . ?
C111 C110 N11 125.7(4) . . ?
C115 C110 N11 114.1(3) . . ?
C112 C111 C110 120.0(4) . . ?
C113 C112 C111 119.8(4) . . ?
C112 C113 C114 120.7(4) . . ?
C113 C114 C115 120.5(4) . . ?
C114 C115 C110 118.3(3) . . ?
C114 C115 N12 124.5(4) . . ?
C110 C115 N12 117.2(3) . . ?
C121 C116 C117 119.6(4) . . ?
C121 C116 S 120.6(3) . . ?
C117 C116 S 119.8(3) . . ?
C118 C117 C116 119.7(4) . . ?
C117 C118 C119 121.7(4) . . ?
C118 C119 C120 117.7(4) . . ?
C118 C119 C122 121.4(3) . . ?
C120 C119 C122 120.9(4) . . ?
C121 C120 C119 121.5(4) . . ?
C120 C121 C116 119.7(3) . . ?
C25 N21 C21 116.5(3) . . ?
C25 N21 Cu 121.4(2) . . ?
C21 N21 Cu 122.0(3) . . ?
N21 C21 C22 122.6(4) . . ?
C23 C22 C21 121.1(3) . . ?
C22 C23 C24 115.9(3) . . ?
C22 C23 C23 123.0(4) . 2_767 ?
C24 C23 C23 121.1(4) . 2_767 ?
C25 C24 C23 119.7(4) . . ?
N21 C25 C24 124.2(3) . . ?

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
C19 H19 O1 0.95 2.56 3.486(5) 164.3 2_556
C111 H111 O1 0.95 2.47 3.394(5) 163.9 2_556

_refine_diff_density_max         0.469
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.104

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_4_CuLphen
_database_code_depnum_ccdc_archive 'CCDC 1828644'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C34 H28 Cu N4 O4 S'
_chemical_formula_weight         652.20

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   24.6147(17)
_cell_length_b                   12.9395(8)
_cell_length_c                   21.9303(15)
_cell_angle_alpha                90
_cell_angle_beta                 117.6430(10)
_cell_angle_gamma                90
_cell_volume                     6187.6(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2956
_cell_measurement_theta_min      2.315
_cell_measurement_theta_max      21.632

_exptl_crystal_description       irregular
_exptl_crystal_colour            black
_exptl_crystal_size_max          .30
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .20
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             2696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.818
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.790573
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         '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_reflns_number            17494
_diffrn_reflns_av_unetI/netI     0.1219
_diffrn_reflns_av_R_equivalents  0.0656
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.830
_diffrn_reflns_theta_max         28.037
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             7004
_reflns_number_gt                3610
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7004
_refine_ls_number_parameters     399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0935
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_restrained_S_all      0.819
_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
CG1 H 0.1391 0.6411 0.1432 0.000 Uiso 0 1 d . U P . .
CG2 H 0.2486 0.7140 0.0970 0.000 Uiso 0 1 d . U P . .
CG3 H 0.1738 0.7590 0.0040 0.000 Uiso 0 1 d . U P . .
CG4 H 0.2521 0.6490 0.0873 0.000 Uiso 0 1 d . U P . .
Cu Cu 0.24564(2) 0.94893(3) 0.14466(2) 0.03733(13) Uani 1 1 d . . . . .
S2 S 0.17596(4) 0.85198(6) 0.22595(4) 0.0392(2) Uani 1 1 d . . . . .
O1 O 0.23752(10) 0.83801(16) 0.28015(10) 0.0486(6) Uani 1 1 d . . . . .
O2 O 0.12939(10) 0.87590(16) 0.24636(11) 0.0528(6) Uani 1 1 d . . . . .
N11 N 0.17853(11) 0.93601(18) 0.17381(13) 0.0380(6) Uani 1 1 d . . . . .
N12 N 0.20389(12) 1.07980(18) 0.10781(12) 0.0386(7) Uani 1 1 d . . . . .
O3 O 0.31986(10) 0.99574(15) 0.14381(11) 0.0464(6) Uani 1 1 d . . . . .
O4 O 0.42748(12) 1.02144(18) 0.14905(14) 0.0671(7) Uani 1 1 d . . . . .
C01 C 0.38867(17) 1.1042(3) 0.12798(17) 0.0486(9) Uani 1 1 d . . . . .
C02 C 0.40289(19) 1.1985(3) 0.11025(19) 0.0644(11) Uani 1 1 d . . . . .
H02 H 0.4413 1.2085 0.1127 0.077 Uiso 1 1 calc R U . . .
C03 C 0.3606(2) 1.2798(3) 0.08865(19) 0.0662(12) Uani 1 1 d . . . . .
H03 H 0.3705 1.3430 0.0762 0.079 Uiso 1 1 calc R U . . .
C04 C 0.30504(19) 1.2656(3) 0.08598(17) 0.0557(10) Uani 1 1 d . . . . .
H04 H 0.2771 1.3199 0.0723 0.067 Uiso 1 1 calc R U . . .
C05 C 0.28880(16) 1.1692(2) 0.10368(16) 0.0411(8) Uani 1 1 d . . . . .
C06 C 0.33070(16) 1.0871(2) 0.12586(16) 0.0408(8) Uani 1 1 d . . . . .
C07 C 0.22910(17) 1.1614(2) 0.09720(15) 0.0452(9) Uani 1 1 d . . . . .
H07 H 0.2053 1.2210 0.0839 0.054 Uiso 1 1 calc R U . . .
C08 C 0.14276(15) 1.0799(2) 0.09753(16) 0.0403(8) Uani 1 1 d . . . . .
C09 C 0.09752(17) 1.1484(3) 0.05464(17) 0.0524(9) Uani 1 1 d . . . . .
H09 H 0.1072 1.1985 0.0308 0.063 Uiso 1 1 calc R U . . .
C10 C 0.03935(19) 1.1434(3) 0.0469(2) 0.0647(11) Uani 1 1 d . . . . .
H10 H 0.0099 1.1911 0.0195 0.078 Uiso 1 1 calc R U . . .
C11 C 0.02505(17) 1.0668(3) 0.0803(2) 0.0628(11) Uani 1 1 d . . . . .
H11 H -0.0148 1.0625 0.0746 0.075 Uiso 1 1 calc R U . . .
C12 C 0.06811(15) 0.9960(3) 0.12220(18) 0.0487(9) Uani 1 1 d . . . . .
H12 H 0.0568 0.9447 0.1438 0.058 Uiso 1 1 calc R U . . .
C13 C 0.12856(15) 1.0005(2) 0.13255(16) 0.0402(8) Uani 1 1 d . . . . .
C14 C 0.15445(14) 0.7333(2) 0.18001(16) 0.0378(8) Uani 1 1 d . . . . .
C15 C 0.19052(15) 0.6469(2) 0.20657(17) 0.0459(9) Uani 1 1 d . . . . .
H15 H 0.2252 0.6499 0.2492 0.055 Uiso 1 1 calc R U . . .
C16 C 0.17489(17) 0.5556(3) 0.16949(18) 0.0504(9) Uani 1 1 d . . . . .
H16 H 0.1993 0.4975 0.1878 0.060 Uiso 1 1 calc R U . . .
C17 C 0.12377(17) 0.5488(3) 0.10580(19) 0.0497(9) Uani 1 1 d . . . . .
C18 C 0.08779(17) 0.6355(3) 0.08043(18) 0.0556(10) Uani 1 1 d . . . . .
H18 H 0.0528 0.6326 0.0380 0.067 Uiso 1 1 calc R U . . .
C19 C 0.10304(16) 0.7263(3) 0.11705(18) 0.0512(9) Uani 1 1 d . . . . .
H19 H 0.0782 0.7841 0.0990 0.061 Uiso 1 1 calc R U . . .
C20 C 0.1085(2) 0.4500(3) 0.0640(2) 0.0794(13) Uani 1 1 d . . . . .
H20A H 0.1405 0.4002 0.0871 0.119 Uiso 1 1 calc R U . . .
H20B H 0.1051 0.4644 0.0193 0.119 Uiso 1 1 calc R U . . .
H20C H 0.0704 0.4228 0.0589 0.119 Uiso 1 1 calc R U . . .
C21 C 0.4858(2) 1.0323(4) 0.1521(2) 0.0865(14) Uani 1 1 d . . . . .
H21A H 0.5101 1.0820 0.1873 0.104 Uiso 1 1 calc R U . . .
H21B H 0.4814 1.0568 0.1083 0.104 Uiso 1 1 calc R U . . .
C22 C 0.5166(2) 0.9291(4) 0.1686(3) 0.122(2) Uani 1 1 d . . . . .
H22A H 0.5136 0.8993 0.2070 0.183 Uiso 1 1 calc R U . . .
H22B H 0.5591 0.9373 0.1801 0.183 Uiso 1 1 calc R U . . .
H22C H 0.4971 0.8844 0.1294 0.183 Uiso 1 1 calc R U . . .
N31 N 0.28916(12) 0.81423(18) 0.17831(13) 0.0379(6) Uani 1 1 d . . . . .
N32 N 0.19499(12) 0.84014(19) 0.05108(14) 0.0417(7) Uani 1 1 d . . . . .
C31 C 0.33657(15) 0.8022(3) 0.23949(18) 0.0473(9) Uani 1 1 d . . . . .
H31 H 0.3486 0.8583 0.2694 0.057 Uiso 1 1 calc R U . . .
C32 C 0.36969(16) 0.7111(3) 0.26205(19) 0.0557(10) Uani 1 1 d . . . . .
H32 H 0.4030 0.7065 0.3057 0.067 Uiso 1 1 calc R U . . .
C33 C 0.35181(17) 0.6278(3) 0.2180(2) 0.0546(10) Uani 1 1 d . . . . .
H33 H 0.3730 0.5656 0.2319 0.066 Uiso 1 1 calc R U . . .
C34 C 0.30260(16) 0.6364(2) 0.15344(18) 0.0440(8) Uani 1 1 d . . . . .
C35 C 0.27208(14) 0.7317(2) 0.13460(16) 0.0374(8) Uani 1 1 d . . . . .
C36 C 0.22134(15) 0.7454(2) 0.06731(17) 0.0395(8) Uani 1 1 d . . . . .
C37 C 0.20150(16) 0.6622(3) 0.02049(18) 0.0459(9) Uani 1 1 d . . . . .
C38 C 0.15212(18) 0.6800(3) -0.04440(19) 0.0583(10) Uani 1 1 d . . . . .
H38 H 0.1379 0.6273 -0.0770 0.070 Uiso 1 1 calc R U . . .
C39 C 0.12494(17) 0.7742(3) -0.05975(19) 0.0592(10) Uani 1 1 d . . . . .
H39 H 0.0914 0.7862 -0.1024 0.071 Uiso 1 1 calc R U . . .
C310 C 0.14795(16) 0.8525(3) -0.01089(18) 0.0508(9) Uani 1 1 d . . . . .
H310 H 0.1293 0.9171 -0.0224 0.061 Uiso 1 1 calc R U . . .
C311 C 0.28153(19) 0.5531(3) 0.1056(2) 0.0583(10) Uani 1 1 d . . . . .
H311 H 0.3009 0.4892 0.1182 0.070 Uiso 1 1 calc R U . . .
C312 C 0.2338(2) 0.5655(3) 0.0423(2) 0.0592(11) Uani 1 1 d . . . . .
H312 H 0.2214 0.5101 0.0119 0.071 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
Cu O3 1.933(2) . ?
Cu N12 1.951(2) . ?
Cu N31 1.999(2) . ?
Cu N11 2.036(2) . ?
Cu N32 2.318(3) . ?
S2 O1 1.439(2) . ?
S2 O2 1.444(2) . ?
S2 N11 1.600(2) . ?
S2 C14 1.777(3) . ?
N11 C13 1.412(4) . ?
N12 C07 1.299(4) . ?
N12 C08 1.414(4) . ?
O3 C06 1.312(3) . ?
O4 C01 1.365(4) . ?
O4 C21 1.412(4) . ?
C01 C02 1.375(5) . ?
C01 C06 1.423(4) . ?
C02 C03 1.399(5) . ?
C03 C04 1.354(5) . ?
C04 C05 1.418(4) . ?
C05 C06 1.401(4) . ?
C05 C07 1.413(4) . ?
C08 C09 1.393(4) . ?
C08 C13 1.420(4) . ?
C09 C10 1.363(5) . ?
C10 C11 1.372(5) . ?
C11 C12 1.379(5) . ?
C12 C13 1.398(4) . ?
C14 C19 1.376(4) . ?
C14 C15 1.378(4) . ?
C15 C16 1.383(4) . ?
C16 C17 1.382(5) . ?
C17 C18 1.377(4) . ?
C17 C20 1.516(4) . ?
C18 C19 1.374(4) . ?
C21 C22 1.495(5) . ?
N31 C31 1.317(4) . ?
N31 C35 1.364(4) . ?
N32 C310 1.324(4) . ?
N32 C36 1.355(4) . ?
C31 C32 1.387(4) . ?
C32 C33 1.377(5) . ?
C33 C34 1.375(5) . ?
C34 C35 1.403(4) . ?
C34 C311 1.424(4) . ?
C35 C36 1.435(4) . ?
C36 C37 1.409(4) . ?
C37 C38 1.396(5) . ?
C37 C312 1.440(5) . ?
C38 C39 1.355(5) . ?
C39 C310 1.390(5) . ?
C311 C312 1.349(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
O3 Cu N12 92.44(10) . . ?
O3 Cu N31 85.98(9) . . ?
N12 Cu N31 177.14(11) . . ?
O3 Cu N11 159.53(9) . . ?
N12 Cu N11 81.55(10) . . ?
N31 Cu N11 100.73(10) . . ?
O3 Cu N32 107.72(9) . . ?
N12 Cu N32 101.35(10) . . ?
N31 Cu N32 76.90(10) . . ?
N11 Cu N32 92.67(9) . . ?
O1 S2 O2 117.00(14) . . ?
O1 S2 N11 107.45(13) . . ?
O2 S2 N11 112.09(13) . . ?
O1 S2 C14 106.40(14) . . ?
O2 S2 C14 106.88(14) . . ?
N11 S2 C14 106.39(13) . . ?
C13 N11 S2 123.2(2) . . ?
C13 N11 Cu 110.0(2) . . ?
S2 N11 Cu 125.94(14) . . ?
C07 N12 C08 122.1(3) . . ?
C07 N12 Cu 125.2(2) . . ?
C08 N12 Cu 112.57(19) . . ?
C06 O3 Cu 127.6(2) . . ?
C01 O4 C21 118.3(3) . . ?
O4 C01 C02 124.2(3) . . ?
O4 C01 C06 115.0(3) . . ?
C02 C01 C06 120.8(3) . . ?
C01 C02 C03 121.1(4) . . ?
C04 C03 C02 119.4(4) . . ?
C03 C04 C05 121.0(4) . . ?
C06 C05 C07 123.0(3) . . ?
C06 C05 C04 120.4(3) . . ?
C07 C05 C04 116.6(3) . . ?
O3 C06 C05 124.6(3) . . ?
O3 C06 C01 118.1(3) . . ?
C05 C06 C01 117.3(3) . . ?
N12 C07 C05 126.9(3) . . ?
C09 C08 N12 124.5(3) . . ?
C09 C08 C13 120.4(3) . . ?
N12 C08 C13 115.1(3) . . ?
C10 C09 C08 121.2(4) . . ?
C09 C10 C11 118.9(4) . . ?
C10 C11 C12 121.8(4) . . ?
C11 C12 C13 120.8(4) . . ?
C12 C13 N11 128.6(3) . . ?
C12 C13 C08 116.9(3) . . ?
N11 C13 C08 114.5(3) . . ?
C19 C14 C15 118.9(3) . . ?
C19 C14 S2 121.3(3) . . ?
C15 C14 S2 119.8(2) . . ?
C14 C15 C16 119.7(3) . . ?
C17 C16 C15 121.5(3) . . ?
C18 C17 C16 118.0(3) . . ?
C18 C17 C20 120.7(3) . . ?
C16 C17 C20 121.3(3) . . ?
C19 C18 C17 120.7(3) . . ?
C18 C19 C14 121.2(3) . . ?
O4 C21 C22 108.3(4) . . ?
C31 N31 C35 117.5(3) . . ?
C31 N31 Cu 123.3(2) . . ?
C35 N31 Cu 119.0(2) . . ?
C310 N32 C36 117.6(3) . . ?
C310 N32 Cu 133.7(2) . . ?
C36 N32 Cu 108.8(2) . . ?
N31 C31 C32 124.1(3) . . ?
C33 C32 C31 118.1(3) . . ?
C34 C33 C32 120.1(3) . . ?
C33 C34 C35 118.0(3) . . ?
C33 C34 C311 122.9(3) . . ?
C35 C34 C311 119.1(3) . . ?
N31 C35 C34 122.2(3) . . ?
N31 C35 C36 117.6(3) . . ?
C34 C35 C36 120.2(3) . . ?
N32 C36 C37 122.5(3) . . ?
N32 C36 C35 117.6(3) . . ?
C37 C36 C35 119.8(3) . . ?
C38 C37 C36 117.4(3) . . ?
C38 C37 C312 124.5(3) . . ?
C36 C37 C312 118.0(3) . . ?
C39 C38 C37 119.8(3) . . ?
C38 C39 C310 119.1(4) . . ?
N32 C310 C39 123.5(3) . . ?
C312 C311 C34 120.9(3) . . ?
C311 C312 C37 121.9(3) . . ?

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
C37 CG3 N32 1.391(3) 1.393(3) 2.424(4) 121.06(18) .
C12 H12 O2 0.93 2.31 2.880(4) 119.5 .

_refine_diff_density_max         0.314
_refine_diff_density_min         -0.435
_refine_diff_density_rms         0.086


# SQUEEZE RESULTS (Version =  30715)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 1.000 -0.014 0.250 115 30 ' '
2 1.000 0.014 0.750 115 30 ' '
3 0.500 0.486 0.250 115 30 ' '
4 0.500 0.514 0.750 115 30 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?


_shelxl_version_number           2014/6




####################################################################### 
# 
# 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_7_4-4bipy_bipy
_database_code_depnum_ccdc_archive 'CCDC 1828643'
_audit_update_record             
;
2018-03-09 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H30 Cu N5 O3 S'
_chemical_formula_weight         712.28

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'
N N 0.0061 0.0033 '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                   9.203(3)
_cell_length_b                   12.352(4)
_cell_length_c                   15.197(5)
_cell_angle_alpha                70.384(6)
_cell_angle_beta                 83.857(5)
_cell_angle_gamma                86.570(5)
_cell_volume                     1617.5(9)
_cell_formula_units_Z            2

_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1977
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.27

_exptl_crystal_description       Plate
_exptl_crystal_colour            green

_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.788
_shelx_estimated_absorpt_T_min   0.708
_shelx_estimated_absorpt_T_max   0.947
_exptl_absorpt_correction_type   psi-scans
_exptl_absorpt_correction_T_min  0.7083
_exptl_absorpt_correction_T_max  0.9469
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(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_reflns_number            29072
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.751
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7401
_reflns_number_gt                6023
_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-97 (Sheldrick, 1990)'

_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP3 for windows (Farrugia, 1997)'
_computing_publication_material  ?

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0334P)²+1.4942P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7401
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0844
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
CT1 H 1.5635 0.1391 -0.0980 0.000 Uiso 0 1 d . U P . .
CT2 H 0.8546 -0.1829 0.3115 0.000 Uiso 0 1 d . U P . .
Cu Cu 0.92457(3) 0.28523(2) 0.24265(2) 0.01263(8) Uani 1 1 d . . . . .
N31 N 1.08120(19) 0.22400(15) 0.14231(13) 0.0167(4) Uani 1 1 d . . . . .
N32 N 1.6843(2) 0.11728(16) -0.15492(14) 0.0214(4) Uani 1 1 d . . . . .
C31 C 1.0666(2) 0.2385(2) 0.05225(15) 0.0191(5) Uani 1 1 d . . . . .
H31 H 0.9757 0.2626 0.0300 0.023 Uiso 1 1 calc R U . . .
C32 C 1.1786(2) 0.21979(19) -0.00953(16) 0.0188(5) Uani 1 1 d . . . . .
H32 H 1.1628 0.2328 -0.0717 0.023 Uiso 1 1 calc R U . . .
C33 C 1.3156(2) 0.18120(18) 0.02194(15) 0.0148(4) Uani 1 1 d . . . . .
C34 C 1.3298(2) 0.16266(18) 0.11658(15) 0.0157(4) Uani 1 1 d . . . . .
H34 H 1.4181 0.1354 0.1416 0.019 Uiso 1 1 calc R U . . .
C35 C 1.2123(2) 0.18505(18) 0.17242(15) 0.0171(4) Uani 1 1 d . . . . .
H35 H 1.2245 0.1723 0.2351 0.021 Uiso 1 1 calc R U . . .
C36 C 1.4415(2) 0.16087(17) -0.04064(15) 0.0157(4) Uani 1 1 d . . . . .
C37 C 1.4246(2) 0.13815(19) -0.12253(16) 0.0191(5) Uani 1 1 d . . . . .
H37 H 1.3317 0.1365 -0.1407 0.023 Uiso 1 1 calc R U . . .
C38 C 1.5467(2) 0.11805(19) -0.17664(16) 0.0209(5) Uani 1 1 d . . . . .
H38 H 1.5326 0.1042 -0.2316 0.025 Uiso 1 1 calc R U . . .
C39 C 1.5843(2) 0.16172(19) -0.01801(16) 0.0189(5) Uani 1 1 d . . . . .
H39 H 1.6018 0.1777 0.0355 0.023 Uiso 1 1 calc R U . . .
C310 C 1.6998(2) 0.13857(19) -0.07575(16) 0.0208(5) Uani 1 1 d . . . . .
H310 H 1.7939 0.1377 -0.0585 0.025 Uiso 1 1 calc R U . . .
S1 S 0.73029(6) 0.07316(4) 0.25026(4) 0.01446(12) Uani 1 1 d . . . . .
O2 O 0.57460(16) 0.06579(13) 0.27799(11) 0.0177(3) Uani 1 1 d . . . . .
O1 O 0.77297(17) 0.12482(13) 0.15124(10) 0.0200(3) Uani 1 1 d . . . . .
N11 N 1.00392(18) 0.23417(14) 0.36481(12) 0.0119(3) Uani 1 1 d . . . . .
N12 N 0.81285(18) 0.14003(15) 0.30227(12) 0.0135(4) Uani 1 1 d . . . . .
O11 O 1.03465(16) 0.42564(12) 0.20562(10) 0.0160(3) Uani 1 1 d . . . . .
C11 C 1.1528(2) 0.43913(18) 0.24000(14) 0.0134(4) Uani 1 1 d . . . . .
C12 C 1.2261(2) 0.54643(18) 0.19563(15) 0.0164(4) Uani 1 1 d . . . . .
H12 H 1.1867 0.6017 0.1451 0.020 Uiso 1 1 calc R U . . .
C13 C 1.3505(2) 0.56906(18) 0.22545(16) 0.0184(5) Uani 1 1 d . . . . .
H13 H 1.3924 0.6405 0.1962 0.022 Uiso 1 1 calc R U . . .
C14 C 1.4196(2) 0.48661(18) 0.30052(16) 0.0172(4) Uani 1 1 d . . . . .
C15 C 1.5548(3) 0.5072(2) 0.32670(17) 0.0240(5) Uani 1 1 d . . . . .
H15 H 1.5983 0.5779 0.2969 0.029 Uiso 1 1 calc R U . . .
C16 C 1.6233(3) 0.4247(2) 0.39536(17) 0.0259(5) Uani 1 1 d . . . . .
H16 H 1.7118 0.4399 0.4127 0.031 Uiso 1 1 calc R U . . .
C17 C 1.5597(2) 0.3174(2) 0.43945(16) 0.0198(5) Uani 1 1 d . . . . .
H17 H 1.6070 0.2609 0.4853 0.024 Uiso 1 1 calc R U . . .
C18 C 1.4272(2) 0.29518(19) 0.41516(15) 0.0164(4) Uani 1 1 d . . . . .
H18 H 1.3868 0.2233 0.4447 0.020 Uiso 1 1 calc R U . . .
C19 C 1.3515(2) 0.37916(18) 0.34649(14) 0.0136(4) Uani 1 1 d . . . . .
C110 C 1.2115(2) 0.35912(17) 0.31975(14) 0.0123(4) Uani 1 1 d . . . . .
C111 C 1.1257(2) 0.26678(17) 0.38264(15) 0.0125(4) Uani 1 1 d . . . . .
H111 H 1.1599 0.2272 0.4406 0.015 Uiso 1 1 calc R U . . .
C112 C 0.9122(2) 0.15508(17) 0.43540(14) 0.0123(4) Uani 1 1 d . . . . .
C113 C 0.9152(2) 0.13303(18) 0.53082(15) 0.0154(4) Uani 1 1 d . . . . .
H113 H 0.9842 0.1676 0.5524 0.019 Uiso 1 1 calc R U . . .
C114 C 0.8149(2) 0.05920(19) 0.59432(15) 0.0171(4) Uani 1 1 d . . . . .
H114 H 0.8174 0.0435 0.6584 0.021 Uiso 1 1 calc R U . . .
C115 C 0.7108(2) 0.00898(18) 0.56135(15) 0.0160(4) Uani 1 1 d . . . . .
H115 H 0.6436 -0.0403 0.6038 0.019 Uiso 1 1 calc R U . . .
C116 C 0.7062(2) 0.03148(17) 0.46603(15) 0.0138(4) Uani 1 1 d . . . . .
H116 H 0.6359 -0.0027 0.4450 0.017 Uiso 1 1 calc R U . . .
C117 C 0.8067(2) 0.10538(17) 0.40119(14) 0.0124(4) Uani 1 1 d . . . . .
C118 C 0.7996(2) -0.07054(18) 0.28461(15) 0.0155(4) Uani 1 1 d . . . . .
C119 C 0.7156(2) -0.15868(19) 0.34699(15) 0.0160(4) Uani 1 1 d . . . . .
H119 H 0.6224 -0.1426 0.3706 0.019 Uiso 1 1 calc R U . . .
C120 C 0.7711(2) -0.27089(19) 0.37396(15) 0.0175(4) Uani 1 1 d . . . . .
H120 H 0.7146 -0.3297 0.4156 0.021 Uiso 1 1 calc R U . . .
C121 C 0.9104(2) -0.29622(19) 0.33932(16) 0.0190(5) Uani 1 1 d . . . . .
C122 C 0.9927(2) -0.2065(2) 0.27569(16) 0.0205(5) Uani 1 1 d . . . . .
H122 H 1.0855 -0.2224 0.2514 0.025 Uiso 1 1 calc R U . . .
C123 C 0.9382(2) -0.09473(19) 0.24849(15) 0.0185(5) Uani 1 1 d . . . . .
H123 H 0.9940 -0.0359 0.2062 0.022 Uiso 1 1 calc R U . . .
C124 C 0.9707(3) -0.4177(2) 0.37019(19) 0.0276(5) Uani 1 1 d . . . . .
H12A H 0.9260 -0.4592 0.4315 0.041 Uiso 1 1 calc R U . . .
H12B H 1.0745 -0.4170 0.3723 0.041 Uiso 1 1 calc R U . . .
H12C H 0.9502 -0.4545 0.3266 0.041 Uiso 1 1 calc R U . . .
N21 N 0.76930(18) 0.37348(15) 0.15787(12) 0.0143(4) Uani 1 1 d . . . . .
C21 C 0.6282(2) 0.34656(18) 0.18069(15) 0.0149(4) Uani 1 1 d . . . . .
H21 H 0.6014 0.2932 0.2392 0.018 Uiso 1 1 calc R U . . .
C22 C 0.5210(2) 0.39441(18) 0.12133(15) 0.0143(4) Uani 1 1 d . . . . .
H22 H 0.4244 0.3730 0.1403 0.017 Uiso 1 1 calc R U . . .
C23 C 0.5566(2) 0.47479(17) 0.03298(14) 0.0130(4) Uani 1 1 d . . . . .
C24 C 0.7031(2) 0.50596(18) 0.01136(15) 0.0170(4) Uani 1 1 d . . . . .
H24 H 0.7327 0.5611 -0.0457 0.020 Uiso 1 1 calc R U . . .
C25 C 0.8036(2) 0.45457(19) 0.07508(15) 0.0175(4) Uani 1 1 d . . . . .
H25 H 0.9001 0.4775 0.0597 0.021 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
Cu O11 1.9452(15) . ?
Cu N11 1.9562(18) . ?
Cu N12 2.0063(17) . ?
Cu N21 2.0384(18) . ?
Cu N31 2.2690(19) . ?
N31 C31 1.340(3) . ?
N31 C35 1.341(3) . ?
N32 C310 1.338(3) . ?
N32 C38 1.341(3) . ?
C31 C32 1.381(3) . ?
C32 C33 1.397(3) . ?
C33 C34 1.398(3) . ?
C33 C36 1.483(3) . ?
C34 C35 1.376(3) . ?
C36 C37 1.390(3) . ?
C36 C39 1.395(3) . ?
C37 C38 1.381(3) . ?
C39 C310 1.383(3) . ?
S1 O1 1.4438(16) . ?
S1 O2 1.4490(16) . ?
S1 N12 1.5894(17) . ?
S1 C118 1.773(2) . ?
N11 C111 1.298(3) . ?
N11 C112 1.421(2) . ?
N12 C117 1.414(3) . ?
O11 C11 1.298(2) . ?
C11 C110 1.418(3) . ?
C11 C12 1.441(3) . ?
C12 C13 1.353(3) . ?
C13 C14 1.428(3) . ?
C14 C15 1.408(3) . ?
C14 C19 1.423(3) . ?
C15 C16 1.369(3) . ?
C16 C17 1.400(3) . ?
C17 C18 1.380(3) . ?
C18 C19 1.411(3) . ?
C19 C110 1.451(3) . ?
C110 C111 1.433(3) . ?
C112 C113 1.386(3) . ?
C112 C117 1.409(3) . ?
C113 C114 1.391(3) . ?
C114 C115 1.391(3) . ?
C115 C116 1.385(3) . ?
C116 C117 1.401(3) . ?
C118 C119 1.390(3) . ?
C118 C123 1.390(3) . ?
C119 C120 1.389(3) . ?
C120 C121 1.391(3) . ?
C121 C122 1.401(3) . ?
C121 C124 1.505(3) . ?
C122 C123 1.381(3) . ?
N21 C25 1.339(3) . ?
N21 C21 1.340(3) . ?
C21 C22 1.378(3) . ?
C22 C23 1.395(3) . ?
C23 C24 1.398(3) . ?
C23 C23 1.485(4) 2_665 ?
C24 C25 1.380(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
O11 Cu N11 90.06(7) . . ?
O11 Cu N12 170.67(7) . . ?
N11 Cu N12 81.51(7) . . ?
O11 Cu N21 88.90(7) . . ?
N11 Cu N21 150.02(7) . . ?
N12 Cu N21 96.40(7) . . ?
O11 Cu N31 88.53(7) . . ?
N11 Cu N31 107.98(7) . . ?
N12 Cu N31 97.82(7) . . ?
N21 Cu N31 101.95(7) . . ?
C31 N31 C35 116.20(19) . . ?
C31 N31 Cu 127.37(15) . . ?
C35 N31 Cu 115.57(14) . . ?
C310 N32 C38 116.1(2) . . ?
N31 C31 C32 123.8(2) . . ?
C31 C32 C33 119.6(2) . . ?
C32 C33 C34 116.6(2) . . ?
C32 C33 C36 122.6(2) . . ?
C34 C33 C36 120.75(19) . . ?
C35 C34 C33 119.5(2) . . ?
N31 C35 C34 124.2(2) . . ?
C37 C36 C39 116.8(2) . . ?
C37 C36 C33 122.65(19) . . ?
C39 C36 C33 120.5(2) . . ?
C38 C37 C36 119.6(2) . . ?
N32 C38 C37 124.1(2) . . ?
C310 C39 C36 119.5(2) . . ?
N32 C310 C39 124.0(2) . . ?
O1 S1 O2 116.31(9) . . ?
O1 S1 N12 106.52(9) . . ?
O2 S1 N12 113.01(10) . . ?
O1 S1 C118 107.21(10) . . ?
O2 S1 C118 105.85(9) . . ?
N12 S1 C118 107.51(10) . . ?
C111 N11 C112 121.89(17) . . ?
C111 N11 Cu 125.67(14) . . ?
C112 N11 Cu 112.44(13) . . ?
C117 N12 S1 121.97(14) . . ?
C117 N12 Cu 110.95(12) . . ?
S1 N12 Cu 126.95(10) . . ?
C11 O11 Cu 125.98(13) . . ?
O11 C11 C110 125.29(18) . . ?
O11 C11 C12 116.98(18) . . ?
C110 C11 C12 117.66(18) . . ?
C13 C12 C11 121.8(2) . . ?
C12 C13 C14 122.00(19) . . ?
C15 C14 C19 119.9(2) . . ?
C15 C14 C13 121.81(19) . . ?
C19 C14 C13 118.25(19) . . ?
C16 C15 C14 121.0(2) . . ?
C15 C16 C17 119.8(2) . . ?
C18 C17 C16 120.3(2) . . ?
C17 C18 C19 121.5(2) . . ?
C18 C19 C14 117.50(19) . . ?
C18 C19 C110 122.96(18) . . ?
C14 C19 C110 119.52(19) . . ?
C11 C110 C111 120.81(18) . . ?
C11 C110 C19 120.14(18) . . ?
C111 C110 C19 118.44(18) . . ?
N11 C111 C110 124.91(19) . . ?
C113 C112 C117 120.88(18) . . ?
C113 C112 N11 124.30(18) . . ?
C117 C112 N11 114.64(18) . . ?
C112 C113 C114 120.00(19) . . ?
C113 C114 C115 119.6(2) . . ?
C116 C115 C114 120.77(19) . . ?
C115 C116 C117 120.32(19) . . ?
C116 C117 C112 118.42(19) . . ?
C116 C117 N12 127.09(18) . . ?
C112 C117 N12 114.46(17) . . ?
C119 C118 C123 120.1(2) . . ?
C119 C118 S1 120.22(17) . . ?
C123 C118 S1 119.64(16) . . ?
C120 C119 C118 119.8(2) . . ?
C119 C120 C121 120.7(2) . . ?
C120 C121 C122 118.7(2) . . ?
C120 C121 C124 120.4(2) . . ?
C122 C121 C124 121.0(2) . . ?
C123 C122 C121 121.0(2) . . ?
C122 C123 C118 119.7(2) . . ?
C25 N21 C21 117.19(18) . . ?
C25 N21 Cu 122.14(14) . . ?
C21 N21 Cu 120.52(14) . . ?
N21 C21 C22 122.94(19) . . ?
C21 C22 C23 120.31(19) . . ?
C22 C23 C24 116.33(18) . . ?
C22 C23 C23 121.1(2) . 2_665 ?
C24 C23 C23 122.5(2) . 2_665 ?
C25 C24 C23 119.71(19) . . ?
N21 C25 C24 123.39(19) . . ?

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
C34 H34 O2 0.93 2.53 3.378(3) 151.7 1_655
C39 H39 O1 0.93 2.39 3.148(3) 138.8 1_655
C115 H115 O2 0.93 2.51 3.334(3) 148.4 2_656
C122 H122 N32 0.93 2.59 3.360(3) 140.3 2_855
C113 H113 CT2 0.93 2.73 3.584(2) 152.6 2_756
C13 H13 CT1 0.93 2.66 3.563(2) 163.8 2_865
C31 H31 O1 0.93 2.70 3.115(3) 107.7 .
C124 H12C O11 0.96 2.75 3.625(3) 152.1 1_545

_refine_diff_density_max         0.401
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.072

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_HL1_Sir2004
_database_code_depnum_ccdc_archive 'CCDC 1828640'
_audit_update_record             
;
2018-03-13 deposited with the CCDC.
2018-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H21 N2 O4 S, H2 O'

_chemical_formula_sum            'C22 H23 N2 O5 S'
_chemical_formula_weight         427.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      Orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        Pbn2(1)
_space_group_name_Hall           'P 2c -2ab'

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

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

_cell_length_a                   9.278(16)
_cell_length_b                   11.646(13)
_cell_length_c                   39.24(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4240(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13
_cell_measurement_theta_min      22.26
_cell_measurement_theta_max      23.869

_exptl_crystal_description       Prism
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_F_000             1800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.60
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    1.666
_shelx_estimated_absorpt_T_min   0.435
_shelx_estimated_absorpt_T_max   0.593
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.2401
_exptl_absorpt_correction_T_max  0.5612
_exptl_absorpt_correction_T_ave  0.4887
_exptl_absorpt_Rmerge_before     0.0215
_exptl_absorpt_Rmerge_after      0.0215
_exptl_absorpt_theta_corr_max    0.9995
_exptl_absorpt_theta_corr_min    0.4723


_exptl_absorpt_factor_muR        0.563
_exptl_absorpt_process_details   
;
North A.C.T., Phillips D.C. & Mathews F.S. (1968) Acta. Cryst. A24, 351
Number of psi-scan sets used was   7
Theta correction was applied.
Weighted transmission curves were used.
No Fourier smoothing was applied.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MACH3 Enraf Nonius'
_diffrn_measurement_method       omega/2-theta
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4442
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       49
_diffrn_reflns_theta_min         4.507
_diffrn_reflns_theta_max         75.169
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.506
_diffrn_reflns_point_group_measured_fraction_full 0.508
_reflns_number_total             4441
_reflns_number_gt                3725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_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       'CAD4-Express Software (Nonius, 1994)'
_computing_cell_refinement       'CAD4-Express Software (Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_structure_solution    SIR2004
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Ortep3 for Windows (Farrugia, 1997)'
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1938P)²+4.3741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4441
_refine_ls_number_parameters     564
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0781
_refine_ls_wR_factor_ref         0.2863
_refine_ls_wR_factor_gt          0.2059
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
O1 O 0.3462(10) 0.2188(8) 0.4796(3) 0.078(2) Uani 1 1 d D . . . .
O2 O -0.3382(10) 0.0323(7) 0.1844(2) 0.075(2) Uani 1 1 d D . . . .
H22 H -0.431(13) 0.05(3) 0.187(11) 0.4(2) Uiso 1 1 d D . . . .
H21 H -0.259(7) 0.023(8) 0.171(2) 0.05(2) Uiso 1 1 d D . . . .
H11 H 0.250(6) 0.21(3) 0.478(8) 0.26(15) Uiso 1 1 d D . . . .
H12 H 0.334(18) 0.153(7) 0.468(3) 0.11(5) Uiso 1 1 d D . . . .
S1 S 0.1321(2) -0.00245(16) 0.42353(6) 0.0479(5) Uani 1 1 d . . . . .
O11 O 0.0544(7) 0.2003(6) 0.49852(18) 0.0596(16) Uani 1 1 d . . . . .
H11A H 0.1307 0.2351 0.4962 0.089 Uiso 1 1 calc R U . . .
O12 O 0.1596(8) 0.3796(6) 0.53245(19) 0.0662(18) Uani 1 1 d . . . . .
O13 O 0.0530(8) 0.0995(5) 0.41473(18) 0.0615(17) Uani 1 1 d . . . . .
O14 O 0.2741(7) 0.0095(7) 0.4365(2) 0.067(2) Uani 1 1 d . . . . .
N11 N -0.1594(8) 0.0798(6) 0.47947(17) 0.0437(14) Uani 1 1 d . . . . .
N12 N 0.0407(8) -0.0707(6) 0.45279(17) 0.0465(15) Uani 1 1 d . . . . .
C11 C -0.0366(10) 0.2640(7) 0.5157(2) 0.0493(18) Uani 1 1 d . . . . .
C12 C 0.0132(12) 0.3620(7) 0.5340(2) 0.055(2) Uani 1 1 d . . . . .
C13 C -0.0834(13) 0.4297(8) 0.5510(2) 0.060(2) Uani 1 1 d . . . . .
H13 H -0.0487 0.4926 0.5631 0.073 Uiso 1 1 calc R U . . .
C14 C -0.2302(14) 0.4090(9) 0.5512(3) 0.061(3) Uani 1 1 d . . . . .
H14 H -0.2930 0.4578 0.5627 0.073 Uiso 1 1 calc R U . . .
C15 C -0.2809(12) 0.3145(9) 0.5340(2) 0.055(2) Uani 1 1 d . . . . .
H15 H -0.3792 0.2988 0.5342 0.066 Uiso 1 1 calc R U . . .
C16 C -0.1857(11) 0.2398(8) 0.5158(2) 0.0509(19) Uani 1 1 d . . . . .
C17 C 0.2220(14) 0.4766(11) 0.5492(3) 0.072(3) Uani 1 1 d . . . . .
H17A H 0.1922 0.4782 0.5729 0.087 Uiso 1 1 calc R U . . .
H17B H 0.1896 0.5470 0.5385 0.087 Uiso 1 1 calc R U . . .
C18 C 0.3796(13) 0.4680(13) 0.5471(3) 0.078(3) Uani 1 1 d . . . . .
H18A H 0.4131 0.4101 0.5626 0.117 Uiso 1 1 calc R U . . .
H18B H 0.4219 0.5406 0.5530 0.117 Uiso 1 1 calc R U . . .
H18C H 0.4068 0.4478 0.5242 0.117 Uiso 1 1 calc R U . . .
C19 C -0.2437(9) 0.1478(8) 0.4974(3) 0.046(2) Uani 1 1 d . . . . .
H19 H -0.3426 0.1345 0.4979 0.055 Uiso 1 1 calc R U . . .
C110 C -0.2114(10) -0.0162(7) 0.4604(2) 0.0445(17) Uani 1 1 d . . . . .
C111 C -0.3580(9) -0.0358(9) 0.4547(2) 0.0513(19) Uani 1 1 d . . . . .
H111 H -0.4268 0.0148 0.4632 0.062 Uiso 1 1 calc R U . . .
C112 C -0.3989(11) -0.1310(9) 0.4365(3) 0.060(2) Uani 1 1 d . . . . .
H112 H -0.4966 -0.1435 0.4326 0.072 Uiso 1 1 calc R U . . .
C113 C -0.3024(12) -0.2079(9) 0.4237(3) 0.058(2) Uani 1 1 d . . . . .
H113 H -0.3333 -0.2730 0.4121 0.070 Uiso 1 1 calc R U . . .
C114 C -0.1566(11) -0.1865(8) 0.4284(2) 0.0502(19) Uani 1 1 d . . . . .
H114 H -0.0887 -0.2366 0.4193 0.060 Uiso 1 1 calc R U . . .
C115 C -0.1115(9) -0.0908(7) 0.4466(2) 0.0415(16) Uani 1 1 d . . . . .
C116 C 0.1402(9) -0.0890(8) 0.3873(2) 0.0484(18) Uani 1 1 d . . . . .
C117 C 0.2185(12) -0.1918(8) 0.3878(3) 0.055(2) Uani 1 1 d . . . . .
H117 H 0.2692 -0.2130 0.4072 0.066 Uiso 1 1 calc R U . . .
C118 C 0.2206(14) -0.2611(9) 0.3595(3) 0.061(2) Uani 1 1 d . . . . .
H118 H 0.2739 -0.3287 0.3601 0.074 Uiso 1 1 calc R U . . .
C119 C 0.1478(12) -0.2341(9) 0.3310(3) 0.063(3) Uani 1 1 d . . . . .
C120 C 0.0677(13) -0.1339(10) 0.3307(2) 0.068(3) Uani 1 1 d . . . . .
H120 H 0.0163 -0.1143 0.3113 0.082 Uiso 1 1 calc R U . . .
C121 C 0.0628(12) -0.0637(9) 0.3583(3) 0.065(2) Uani 1 1 d . . . . .
H121 H 0.0064 0.0023 0.3577 0.078 Uiso 1 1 calc R U . . .
C122 C 0.152(2) -0.3135(12) 0.3003(3) 0.089(4) Uani 1 1 d . . . . .
H12A H 0.2358 -0.2967 0.2868 0.134 Uiso 1 1 calc R U . . .
H12B H 0.0669 -0.3021 0.2868 0.134 Uiso 1 1 calc R U . . .
H12C H 0.1559 -0.3918 0.3078 0.134 Uiso 1 1 calc R U . . .
S2 S -0.1321(2) 0.25801(16) 0.24005(5) 0.0488(5) Uani 1 1 d . . . . .
O23 O -0.2733(8) 0.2467(6) 0.2265(2) 0.065(2) Uani 1 1 d . . . . .
O24 O -0.0527(8) 0.1563(5) 0.24922(19) 0.0621(17) Uani 1 1 d . . . . .
O21 O -0.0496(7) 0.0557(5) 0.16395(18) 0.0594(15) Uani 1 1 d . . . . .
H21A H -0.0082 0.1053 0.1751 0.089 Uiso 1 1 calc R U . . .
O22 O -0.1474(9) -0.1206(7) 0.1296(2) 0.071(2) Uani 1 1 d . . . . .
N21 N -0.0407(7) 0.3267(6) 0.21148(17) 0.0450(14) Uani 1 1 d . . . . .
N22 N 0.1650(8) 0.1786(6) 0.18505(17) 0.0478(15) Uani 1 1 d . . . . .
C21 C 0.0449(11) -0.0077(7) 0.1486(2) 0.0518(19) Uani 1 1 d . . . . .
C22 C -0.0022(12) -0.1080(8) 0.1295(2) 0.058(2) Uani 1 1 d . . . . .
C23 C 0.0981(14) -0.1765(9) 0.1131(2) 0.063(3) Uani 1 1 d . . . . .
H23 H 0.0680 -0.2410 0.1011 0.076 Uiso 1 1 calc R U . . .
C24 C 0.2462(12) -0.1486(10) 0.1148(3) 0.062(3) Uani 1 1 d . . . . .
H24 H 0.3122 -0.1942 0.1031 0.074 Uiso 1 1 calc R U . . .
C25 C 0.2939(12) -0.0585(9) 0.1326(3) 0.058(2) Uani 1 1 d . . . . .
H25 H 0.3922 -0.0441 0.1341 0.070 Uiso 1 1 calc R U . . .
C26 C 0.1955(10) 0.0144(7) 0.1491(2) 0.0482(18) Uani 1 1 d . . . . .
C27 C -0.2011(16) -0.2233(10) 0.1140(3) 0.075(3) Uani 1 1 d . . . . .
H27A H -0.1646 -0.2907 0.1256 0.090 Uiso 1 1 calc R U . . .
H27B H -0.1720 -0.2269 0.0902 0.090 Uiso 1 1 calc R U . . .
C28 C -0.3617(16) -0.2172(13) 0.1168(4) 0.087(4) Uani 1 1 d . . . . .
H28A H -0.3908 -0.2427 0.1390 0.131 Uiso 1 1 calc R U . . .
H28B H -0.4046 -0.2657 0.0998 0.131 Uiso 1 1 calc R U . . .
H28C H -0.3928 -0.1394 0.1134 0.131 Uiso 1 1 calc R U . . .
C29 C 0.2487(10) 0.1127(8) 0.1680(3) 0.047(2) Uani 1 1 d . . . . .
H29 H 0.3469 0.1283 0.1678 0.056 Uiso 1 1 calc R U . . .
C210 C 0.2145(11) 0.2713(7) 0.2045(2) 0.0450(17) Uani 1 1 d . . . . .
C211 C 0.3600(10) 0.2965(9) 0.2100(2) 0.056(2) Uani 1 1 d . . . . .
H211 H 0.4303 0.2477 0.2013 0.067 Uiso 1 1 calc R U . . .
C212 C 0.4007(11) 0.3918(10) 0.2280(2) 0.058(2) Uani 1 1 d . . . . .
H212 H 0.4981 0.4070 0.2314 0.069 Uiso 1 1 calc R U . . .
C213 C 0.2993(12) 0.4650(9) 0.2411(3) 0.057(2) Uani 1 1 d . . . . .
H213 H 0.3289 0.5287 0.2536 0.068 Uiso 1 1 calc R U . . .
C214 C 0.1532(11) 0.4458(7) 0.2361(2) 0.050(2) Uani 1 1 d . . . . .
H214 H 0.0852 0.4973 0.2444 0.060 Uiso 1 1 calc R U . . .
C215 C 0.1094(9) 0.3465(7) 0.2180(2) 0.0407(16) Uani 1 1 d . . . . .
C216 C -0.1391(9) 0.3460(8) 0.2766(2) 0.0507(19) Uani 1 1 d . . . . .
C217 C -0.2242(11) 0.4465(7) 0.2753(3) 0.052(2) Uani 1 1 d . . . . .
H217 H -0.2770 0.4646 0.2559 0.062 Uiso 1 1 calc R U . . .
C218 C -0.2269(13) 0.5169(10) 0.3035(3) 0.058(2) Uani 1 1 d . . . . .
H218 H -0.2833 0.5829 0.3031 0.069 Uiso 1 1 calc R U . . .
C219 C -0.1444(11) 0.4906(9) 0.3333(3) 0.061(2) Uani 1 1 d . . . . .
C220 C -0.0673(14) 0.3900(11) 0.3333(3) 0.076(3) Uani 1 1 d . . . . .
H220 H -0.0148 0.3702 0.3526 0.091 Uiso 1 1 calc R U . . .
C221 C -0.0649(13) 0.3165(9) 0.3053(3) 0.065(3) Uani 1 1 d . . . . .
H221 H -0.0133 0.2481 0.3062 0.078 Uiso 1 1 calc R U . . .
C222 C -0.1500(17) 0.5675(13) 0.3634(3) 0.086(4) Uani 1 1 d . . . . .
H22A H -0.1931 0.5275 0.3822 0.129 Uiso 1 1 calc R U . . .
H22B H -0.2065 0.6342 0.3581 0.129 Uiso 1 1 calc R U . . .
H22C H -0.0541 0.5907 0.3695 0.129 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
O1 H11 0.90(2) . ?
O1 H12 0.90(2) . ?
O2 H22 0.90(2) . ?
O2 H21 0.91(2) . ?
S1 O14 1.419(8) . ?
S1 O13 1.438(6) . ?
S1 N12 1.634(7) . ?
S1 C116 1.743(9) . ?
O11 C11 1.311(10) . ?
O11 H11A 0.8200 . ?
O12 C12 1.375(13) . ?
O12 C17 1.431(14) . ?
N11 C19 1.317(11) . ?
N11 C110 1.431(10) . ?
N12 C115 1.452(11) . ?
C11 C16 1.412(14) . ?
C11 C12 1.424(12) . ?
C12 C13 1.368(13) . ?
C13 C14 1.383(17) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(15) . ?
C14 H14 0.9300 . ?
C15 C16 1.432(13) . ?
C15 H15 0.9300 . ?
C16 C19 1.400(13) . ?
C17 C18 1.468(18) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19 0.9300 . ?
C110 C115 1.380(12) . ?
C110 C111 1.396(13) . ?
C111 C112 1.374(14) . ?
C111 H111 0.9300 . ?
C112 C113 1.361(16) . ?
C112 H112 0.9300 . ?
C113 C114 1.387(15) . ?
C113 H113 0.9300 . ?
C114 C115 1.388(12) . ?
C114 H114 0.9300 . ?
C116 C121 1.377(13) . ?
C116 C117 1.401(13) . ?
C117 C118 1.371(15) . ?
C117 H117 0.9300 . ?
C118 C119 1.344(16) . ?
C118 H118 0.9300 . ?
C119 C120 1.384(16) . ?
C119 C122 1.520(15) . ?
C120 C121 1.358(15) . ?
C120 H120 0.9300 . ?
C121 H121 0.9300 . ?
C122 H12A 0.9600 . ?
C122 H12B 0.9600 . ?
C122 H12C 0.9600 . ?
S2 O23 1.420(8) . ?
S2 O24 1.441(6) . ?
S2 N21 1.617(7) . ?
S2 C216 1.765(10) . ?
O21 C21 1.295(11) . ?
O21 H21A 0.8200 . ?
O22 C22 1.355(13) . ?
O22 C27 1.434(12) . ?
N21 C215 1.435(11) . ?
N22 C29 1.280(12) . ?
N22 C210 1.398(11) . ?
C21 C26 1.420(14) . ?
C21 C22 1.456(12) . ?
C22 C23 1.384(14) . ?
C23 C24 1.414(17) . ?
C23 H23 0.9300 . ?
C24 C25 1.336(16) . ?
C24 H24 0.9300 . ?
C25 C26 1.406(12) . ?
C25 H25 0.9300 . ?
C26 C29 1.450(13) . ?
C27 C28 1.50(2) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 H29 0.9300 . ?
C210 C211 1.399(13) . ?
C210 C215 1.414(13) . ?
C211 C212 1.368(15) . ?
C211 H211 0.9300 . ?
C212 C213 1.370(16) . ?
C212 H212 0.9300 . ?
C213 C214 1.388(14) . ?
C213 H213 0.9300 . ?
C214 C215 1.417(12) . ?
C214 H214 0.9300 . ?
C216 C221 1.363(14) . ?
C216 C217 1.413(12) . ?
C217 C218 1.377(15) . ?
C217 H217 0.9300 . ?
C218 C219 1.432(15) . ?
C218 H218 0.9300 . ?
C219 C220 1.373(16) . ?
C219 C222 1.484(16) . ?
C220 C221 1.391(16) . ?
C220 H220 0.9300 . ?
C221 H221 0.9300 . ?
C222 H22A 0.9600 . ?
C222 H22B 0.9600 . ?
C222 H22C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H11 O1 H12 73(10) . . ?
H22 O2 H21 149(10) . . ?
O14 S1 O13 118.6(5) . . ?
O14 S1 N12 106.1(5) . . ?
O13 S1 N12 107.8(4) . . ?
O14 S1 C116 108.0(4) . . ?
O13 S1 C116 107.7(4) . . ?
N12 S1 C116 108.3(4) . . ?
C11 O11 H11A 109.5 . . ?
C12 O12 C17 119.8(8) . . ?
C19 N11 C110 123.3(8) . . ?
C115 N12 S1 117.8(6) . . ?
O11 C11 C16 121.3(8) . . ?
O11 C11 C12 120.2(9) . . ?
C16 C11 C12 118.5(8) . . ?
C13 C12 O12 125.6(9) . . ?
C13 C12 C11 119.7(10) . . ?
O12 C12 C11 114.7(8) . . ?
C12 C13 C14 123.2(9) . . ?
C12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C15 C14 C13 118.2(10) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 121.4(11) . . ?
C14 C15 H15 119.3 . . ?
C16 C15 H15 119.3 . . ?
C19 C16 C11 122.0(8) . . ?
C19 C16 C15 119.0(9) . . ?
C11 C16 C15 119.0(8) . . ?
O12 C17 C18 108.8(10) . . ?
O12 C17 H17A 109.9 . . ?
C18 C17 H17A 109.9 . . ?
O12 C17 H17B 109.9 . . ?
C18 C17 H17B 109.9 . . ?
H17A C17 H17B 108.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N11 C19 C16 120.4(8) . . ?
N11 C19 H19 119.8 . . ?
C16 C19 H19 119.8 . . ?
C115 C110 C111 119.3(8) . . ?
C115 C110 N11 118.1(8) . . ?
C111 C110 N11 122.6(8) . . ?
C112 C111 C110 118.9(9) . . ?
C112 C111 H111 120.6 . . ?
C110 C111 H111 120.6 . . ?
C113 C112 C111 122.7(10) . . ?
C113 C112 H112 118.6 . . ?
C111 C112 H112 118.6 . . ?
C112 C113 C114 118.3(9) . . ?
C112 C113 H113 120.8 . . ?
C114 C113 H113 120.8 . . ?
C113 C114 C115 120.4(8) . . ?
C113 C114 H114 119.8 . . ?
C115 C114 H114 119.8 . . ?
C110 C115 C114 120.3(8) . . ?
C110 C115 N12 119.1(7) . . ?
C114 C115 N12 120.6(8) . . ?
C121 C116 C117 117.6(9) . . ?
C121 C116 S1 121.8(7) . . ?
C117 C116 S1 120.4(7) . . ?
C118 C117 C116 120.1(9) . . ?
C118 C117 H117 120.0 . . ?
C116 C117 H117 120.0 . . ?
C119 C118 C117 121.8(9) . . ?
C119 C118 H118 119.1 . . ?
C117 C118 H118 119.1 . . ?
C118 C119 C120 118.3(10) . . ?
C118 C119 C122 120.4(11) . . ?
C120 C119 C122 121.3(11) . . ?
C121 C120 C119 121.3(10) . . ?
C121 C120 H120 119.3 . . ?
C119 C120 H120 119.3 . . ?
C120 C121 C116 120.8(9) . . ?
C120 C121 H121 119.6 . . ?
C116 C121 H121 119.6 . . ?
C119 C122 H12A 109.5 . . ?
C119 C122 H12B 109.5 . . ?
H12A C122 H12B 109.5 . . ?
C119 C122 H12C 109.5 . . ?
H12A C122 H12C 109.5 . . ?
H12B C122 H12C 109.5 . . ?
O23 S2 O24 119.2(4) . . ?
O23 S2 N21 105.7(5) . . ?
O24 S2 N21 108.2(4) . . ?
O23 S2 C216 108.9(4) . . ?
O24 S2 C216 107.0(4) . . ?
N21 S2 C216 107.2(4) . . ?
C21 O21 H21A 109.5 . . ?
C22 O22 C27 115.7(9) . . ?
C215 N21 S2 117.7(6) . . ?
C29 N22 C210 123.2(9) . . ?
O21 C21 C26 123.7(8) . . ?
O21 C21 C22 119.6(9) . . ?
C26 C21 C22 116.7(8) . . ?
O22 C22 C23 127.5(9) . . ?
O22 C22 C21 112.5(8) . . ?
C23 C22 C21 120.0(10) . . ?
C22 C23 C24 120.0(10) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 H23 120.0 . . ?
C25 C24 C23 121.7(9) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 120.1(11) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C21 121.5(9) . . ?
C25 C26 C29 119.5(9) . . ?
C21 C26 C29 119.0(7) . . ?
O22 C27 C28 105.9(10) . . ?
O22 C27 H27A 110.5 . . ?
C28 C27 H27A 110.5 . . ?
O22 C27 H27B 110.5 . . ?
C28 C27 H27B 110.5 . . ?
H27A C27 H27B 108.7 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
N22 C29 C26 122.3(8) . . ?
N22 C29 H29 118.9 . . ?
C26 C29 H29 118.9 . . ?
N22 C210 C211 124.3(9) . . ?
N22 C210 C215 117.1(8) . . ?
C211 C210 C215 118.5(8) . . ?
C212 C211 C210 121.1(9) . . ?
C212 C211 H211 119.4 . . ?
C210 C211 H211 119.4 . . ?
C211 C212 C213 120.6(9) . . ?
C211 C212 H212 119.7 . . ?
C213 C212 H212 119.7 . . ?
C212 C213 C214 121.1(9) . . ?
C212 C213 H213 119.5 . . ?
C214 C213 H213 119.5 . . ?
C213 C214 C215 118.9(8) . . ?
C213 C214 H214 120.6 . . ?
C215 C214 H214 120.6 . . ?
C210 C215 C214 119.8(8) . . ?
C210 C215 N21 120.2(7) . . ?
C214 C215 N21 119.9(8) . . ?
C221 C216 C217 121.5(9) . . ?
C221 C216 S2 120.4(7) . . ?
C217 C216 S2 118.1(7) . . ?
C218 C217 C216 118.2(10) . . ?
C218 C217 H217 120.9 . . ?
C216 C217 H217 120.9 . . ?
C217 C218 C219 121.3(10) . . ?
C217 C218 H218 119.3 . . ?
C219 C218 H218 119.3 . . ?
C220 C219 C218 117.4(10) . . ?
C220 C219 C222 122.3(11) . . ?
C218 C219 C222 120.2(10) . . ?
C219 C220 C221 122.2(10) . . ?
C219 C220 H220 118.9 . . ?
C221 C220 H220 118.9 . . ?
C216 C221 C220 119.2(9) . . ?
C216 C221 H221 120.4 . . ?
C220 C221 H221 120.4 . . ?
C219 C222 H22A 109.5 . . ?
C219 C222 H22B 109.5 . . ?
H22A C222 H22B 109.5 . . ?
C219 C222 H22C 109.5 . . ?
H22A C222 H22C 109.5 . . ?
H22B C222 H22C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O14 S1 N12 C115 177.7(6) . . . . ?
O13 S1 N12 C115 49.6(7) . . . . ?
C116 S1 N12 C115 -66.6(7) . . . . ?
C17 O12 C12 C13 -1.1(15) . . . . ?
C17 O12 C12 C11 178.8(9) . . . . ?
O11 C11 C12 C13 178.2(9) . . . . ?
C16 C11 C12 C13 0.2(13) . . . . ?
O11 C11 C12 O12 -1.7(12) . . . . ?
C16 C11 C12 O12 -179.7(8) . . . . ?
O12 C12 C13 C14 178.9(10) . . . . ?
C11 C12 C13 C14 -1.0(15) . . . . ?
C12 C13 C14 C15 1.4(17) . . . . ?
C13 C14 C15 C16 -1.0(16) . . . . ?
O11 C11 C16 C19 -0.5(13) . . . . ?
C12 C11 C16 C19 177.5(8) . . . . ?
O11 C11 C16 C15 -177.8(9) . . . . ?
C12 C11 C16 C15 0.2(12) . . . . ?
C14 C15 C16 C19 -177.2(10) . . . . ?
C14 C15 C16 C11 0.3(14) . . . . ?
C12 O12 C17 C18 173.6(10) . . . . ?
C110 N11 C19 C16 179.5(8) . . . . ?
C11 C16 C19 N11 0.4(14) . . . . ?
C15 C16 C19 N11 177.8(9) . . . . ?
C19 N11 C110 C115 -170.9(8) . . . . ?
C19 N11 C110 C111 10.3(12) . . . . ?
C115 C110 C111 C112 2.0(13) . . . . ?
N11 C110 C111 C112 -179.2(8) . . . . ?
C110 C111 C112 C113 0.4(15) . . . . ?
C111 C112 C113 C114 -2.4(15) . . . . ?
C112 C113 C114 C115 2.0(14) . . . . ?
C111 C110 C115 C114 -2.4(12) . . . . ?
N11 C110 C115 C114 178.8(7) . . . . ?
C111 C110 C115 N12 -179.4(7) . . . . ?
N11 C110 C115 N12 1.7(11) . . . . ?
C113 C114 C115 C110 0.4(13) . . . . ?
C113 C114 C115 N12 177.4(8) . . . . ?
S1 N12 C115 C110 -96.8(8) . . . . ?
S1 N12 C115 C114 86.1(9) . . . . ?
O14 S1 C116 C121 -137.6(9) . . . . ?
O13 S1 C116 C121 -8.4(10) . . . . ?
N12 S1 C116 C121 107.9(9) . . . . ?
O14 S1 C116 C117 47.0(9) . . . . ?
O13 S1 C116 C117 176.3(8) . . . . ?
N12 S1 C116 C117 -67.5(8) . . . . ?
C121 C116 C117 C118 2.3(15) . . . . ?
S1 C116 C117 C118 177.9(9) . . . . ?
C116 C117 C118 C119 -0.6(18) . . . . ?
C117 C118 C119 C120 -0.7(19) . . . . ?
C117 C118 C119 C122 -179.7(12) . . . . ?
C118 C119 C120 C121 0.4(18) . . . . ?
C122 C119 C120 C121 179.3(12) . . . . ?
C119 C120 C121 C116 1.4(18) . . . . ?
C117 C116 C121 C120 -2.7(16) . . . . ?
S1 C116 C121 C120 -178.2(9) . . . . ?
O23 S2 N21 C215 -177.6(6) . . . . ?
O24 S2 N21 C215 -48.8(7) . . . . ?
C216 S2 N21 C215 66.3(7) . . . . ?
C27 O22 C22 C23 7.0(16) . . . . ?
C27 O22 C22 C21 -174.5(9) . . . . ?
O21 C21 C22 O22 1.7(12) . . . . ?
C26 C21 C22 O22 -178.3(8) . . . . ?
O21 C21 C22 C23 -179.7(9) . . . . ?
C26 C21 C22 C23 0.2(13) . . . . ?
O22 C22 C23 C24 177.9(10) . . . . ?
C21 C22 C23 C24 -0.4(15) . . . . ?
C22 C23 C24 C25 1.8(17) . . . . ?
C23 C24 C25 C26 -2.8(16) . . . . ?
C24 C25 C26 C21 2.5(14) . . . . ?
C24 C25 C26 C29 -179.2(10) . . . . ?
O21 C21 C26 C25 178.7(8) . . . . ?
C22 C21 C26 C25 -1.2(12) . . . . ?
O21 C21 C26 C29 0.5(13) . . . . ?
C22 C21 C26 C29 -179.5(8) . . . . ?
C22 O22 C27 C28 -179.3(10) . . . . ?
C210 N22 C29 C26 177.6(8) . . . . ?
C25 C26 C29 N22 -176.3(9) . . . . ?
C21 C26 C29 N22 2.0(13) . . . . ?
C29 N22 C210 C211 -6.0(13) . . . . ?
C29 N22 C210 C215 171.2(8) . . . . ?
N22 C210 C211 C212 177.0(9) . . . . ?
C215 C210 C211 C212 -0.2(14) . . . . ?
C210 C211 C212 C213 0.1(16) . . . . ?
C211 C212 C213 C214 -1.1(15) . . . . ?
C212 C213 C214 C215 2.1(14) . . . . ?
N22 C210 C215 C214 -176.1(7) . . . . ?
C211 C210 C215 C214 1.2(12) . . . . ?
N22 C210 C215 N21 -0.3(11) . . . . ?
C211 C210 C215 N21 177.1(8) . . . . ?
C213 C214 C215 C210 -2.1(12) . . . . ?
C213 C214 C215 N21 -178.0(8) . . . . ?
S2 N21 C215 C210 96.1(8) . . . . ?
S2 N21 C215 C214 -88.1(8) . . . . ?
O23 S2 C216 C221 136.0(9) . . . . ?
O24 S2 C216 C221 5.8(10) . . . . ?
N21 S2 C216 C221 -110.1(9) . . . . ?
O23 S2 C216 C217 -43.5(9) . . . . ?
O24 S2 C216 C217 -173.7(7) . . . . ?
N21 S2 C216 C217 70.4(8) . . . . ?
C221 C216 C217 C218 2.2(15) . . . . ?
S2 C216 C217 C218 -178.3(8) . . . . ?
C216 C217 C218 C219 0.9(16) . . . . ?
C217 C218 C219 C220 -2.6(17) . . . . ?
C217 C218 C219 C222 -179.6(11) . . . . ?
C218 C219 C220 C221 1.5(19) . . . . ?
C222 C219 C220 C221 178.4(12) . . . . ?
C217 C216 C221 C220 -3.3(17) . . . . ?
S2 C216 C221 C220 177.2(9) . . . . ?
C219 C220 C221 C216 1(2) . . . . ?

_refine_diff_density_max         1.646
_refine_diff_density_min         -0.747
_refine_diff_density_rms         0.110

# start Validation Reply Form
_vrf_PLAT417_HL1_Sir2004         
;
PROBLEM: Short Inter D-H..H-D H11 ..H11A 1.35 Ang.
RESPONSE: Position of the hydrogen atoms around both water molecules 
are approximate, with very little accuracy. These atoms should not be taken into account, 
but they were placed (with restrains) in the positions of highest electron density and refined freely.
;
# end Validation Reply Form


