# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

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

data_H2Lnitro
_database_code_depnum_ccdc_archive 'CCDC 1572108'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-07 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         'C10 H12 N4 O2 S'
_chemical_formula_sum            'C10 H12 N4 O2 S'
_chemical_formula_weight         252.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   23.6662(16)
_cell_length_b                   16.5457(11)
_cell_length_c                   12.7144(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.398(5)
_cell_angle_gamma                90
_cell_volume                     4880.4(6)
_cell_formula_units_Z            16
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2730
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      19.18

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.262
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34549
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.512
_diffrn_reflns_theta_max         25.044
_diffrn_reflns_theta_full        25.044
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4312
_reflns_number_gt                2542
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0800P)²+0.0200P] 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         4312
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1324
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.08248(3) 0.17168(5) 0.74421(7) 0.0727(3) Uani 1 1 d . . . . .
S2 S 0.39311(4) 0.02958(5) 0.23059(7) 0.0719(3) Uani 1 1 d . . . . .
C5 C 0.45953(11) 0.08803(15) 0.4740(2) 0.0475(7) Uani 1 1 d . . . . .
C4 C 0.48155(11) 0.09951(16) 0.5822(2) 0.0545(7) Uani 1 1 d . . . . .
H4 H 0.4630 0.0761 0.6326 0.065 Uiso 1 1 calc R U . . .
C16 C 0.12938(11) 0.24670(16) 0.5335(3) 0.0522(7) Uani 1 1 d . . . . .
C8 C 0.37998(12) 0.01311(17) 0.3523(2) 0.0536(7) Uani 1 1 d . . . . .
C2 C 0.55738(11) 0.17963(15) 0.5406(3) 0.0520(7) Uani 1 1 d . . . . .
C15 C 0.05750(11) 0.16547(15) 0.6133(3) 0.0541(7) Uani 1 1 d . . . . .
C3 C 0.53054(12) 0.14517(17) 0.6165(3) 0.0594(8) Uani 1 1 d . . . . .
H3 H 0.5451 0.1526 0.6893 0.071 Uiso 1 1 calc R U . . .
C9 C 0.27688(13) -0.09867(19) 0.4590(3) 0.0664(9) Uani 1 1 d . . . . .
C7 C 0.53675(13) 0.16994(16) 0.4339(3) 0.0615(8) Uani 1 1 d . . . . .
H7 H 0.5555 0.1936 0.3840 0.074 Uiso 1 1 calc R U . . .
C6 C 0.48740(13) 0.12432(18) 0.4001(3) 0.0646(8) Uani 1 1 d . . . . .
H6 H 0.4728 0.1180 0.3271 0.077 Uiso 1 1 calc R U . . .
C21 C 0.16577(13) 0.27644(18) 0.6245(3) 0.0664(8) Uani 1 1 d . . . . .
H21 H 0.1599 0.2622 0.6923 0.080 Uiso 1 1 calc R U . . .
C14 C -0.06044(13) 0.07836(18) 0.4345(3) 0.0685(9) Uani 1 1 d . . . . .
C19 C 0.21920(12) 0.34816(17) 0.5141(3) 0.0636(9) Uani 1 1 d . . . . .
C17 C 0.13910(13) 0.26811(17) 0.4332(3) 0.0639(8) Uani 1 1 d . . . . .
H17 H 0.1153 0.2476 0.3720 0.077 Uiso 1 1 calc R U . . .
C18 C 0.18379(14) 0.31957(18) 0.4230(3) 0.0713(9) Uani 1 1 d . . . . .
H18 H 0.1897 0.3345 0.3555 0.086 Uiso 1 1 calc R U . . .
C20 C 0.21118(13) 0.32762(18) 0.6143(3) 0.0708(9) Uani 1 1 d . . . . .
H20 H 0.2357 0.3476 0.6750 0.085 Uiso 1 1 calc R U . . .
C11 C 0.23689(14) -0.1284(2) 0.3601(3) 0.0962(12) Uani 1 1 d . . . . .
H11C H 0.2243 -0.0836 0.3134 0.144 Uiso 1 1 calc R U . . .
H11A H 0.2041 -0.1538 0.3799 0.144 Uiso 1 1 calc R U . . .
H11B H 0.2567 -0.1667 0.3238 0.144 Uiso 1 1 calc R U . . .
C10 C 0.26473(15) -0.1224(2) 0.5652(3) 0.0933(12) Uani 1 1 d . . . . .
H10B H 0.2911 -0.0952 0.6211 0.140 Uiso 1 1 calc R U . . .
H10A H 0.2693 -0.1798 0.5744 0.140 Uiso 1 1 calc R U . . .
H10C H 0.2259 -0.1076 0.5688 0.140 Uiso 1 1 calc R U . . .
C12 C -0.09370(14) 0.0363(2) 0.5065(3) 0.0892(12) Uani 1 1 d . . . . .
H12C H -0.0679 0.0043 0.5579 0.134 Uiso 1 1 calc R U . . .
H12A H -0.1222 0.0019 0.4646 0.134 Uiso 1 1 calc R U . . .
H12B H -0.1124 0.0757 0.5435 0.134 Uiso 1 1 calc R U . . .
C13 C -0.08198(16) 0.0736(2) 0.3159(3) 0.0988(13) Uani 1 1 d . . . . .
H13A H -0.0596 0.1089 0.2803 0.148 Uiso 1 1 calc R U . . .
H13B H -0.1217 0.0898 0.2991 0.148 Uiso 1 1 calc R U . . .
H13C H -0.0785 0.0191 0.2921 0.148 Uiso 1 1 calc R U . . .
N1 N 0.40960(9) 0.03989(13) 0.44758(19) 0.0524(6) Uani 1 1 d . . . . .
H1 H 0.3955 0.0249 0.5018 0.063 Uiso 1 1 calc R U . . .
N6 N 0.08141(9) 0.19648(13) 0.5333(2) 0.0586(6) Uani 1 1 d . . . . .
H6A H 0.0638 0.1827 0.4701 0.070 Uiso 1 1 calc R U . . .
N2 N 0.33326(10) -0.03273(14) 0.3605(2) 0.0620(7) Uani 1 1 d . . . . .
H2 H 0.3106 -0.0488 0.3029 0.074 Uiso 1 1 calc R U . . .
N5 N 0.00761(10) 0.12473(14) 0.5752(2) 0.0628(7) Uani 1 1 d . . . . .
H5 H -0.0108 0.1024 0.6194 0.075 Uiso 1 1 calc R U . . .
N7 N 0.61007(11) 0.22736(14) 0.5755(3) 0.0635(7) Uani 1 1 d . . . . .
N3 N 0.32143(10) -0.05404(15) 0.4589(2) 0.0640(7) Uani 1 1 d . . . . .
N4 N -0.01353(10) 0.11912(14) 0.4659(2) 0.0644(7) Uani 1 1 d . . . . .
N8 N 0.26698(13) 0.40229(17) 0.5031(3) 0.0844(9) Uani 1 1 d . . . . .
O2 O 0.63056(10) 0.23123(14) 0.6719(2) 0.0873(7) Uani 1 1 d . . . . .
O1 O 0.63200(9) 0.26093(14) 0.5081(2) 0.0859(7) Uani 1 1 d . . . . .
O4 O 0.27243(12) 0.42075(17) 0.4118(3) 0.1148(10) Uani 1 1 d . . . . .
O3 O 0.29875(12) 0.42571(17) 0.5843(3) 0.1124(10) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.656(3) . ?
S2 C8 1.660(3) . ?
C5 C4 1.384(4) . ?
C5 C6 1.387(4) . ?
C5 N1 1.410(3) . ?
C4 C3 1.380(4) . ?
C16 C17 1.386(4) . ?
C16 C21 1.389(4) . ?
C16 N6 1.406(3) . ?
C8 N1 1.349(3) . ?
C8 N2 1.362(3) . ?
C2 C7 1.359(4) . ?
C2 C3 1.379(4) . ?
C2 N7 1.469(4) . ?
C15 N6 1.359(4) . ?
C15 N5 1.363(3) . ?
C9 N3 1.287(3) . ?
C9 C10 1.488(5) . ?
C9 C11 1.499(4) . ?
C7 C6 1.385(4) . ?
C21 C20 1.394(4) . ?
C14 N4 1.293(3) . ?
C14 C12 1.493(5) . ?
C14 C13 1.495(5) . ?
C19 C20 1.369(5) . ?
C19 C18 1.372(4) . ?
C19 N8 1.471(4) . ?
C17 C18 1.384(4) . ?
N2 N3 1.382(3) . ?
N5 N4 1.384(3) . ?
N7 O1 1.220(3) . ?
N7 O2 1.227(3) . ?
N8 O3 1.215(4) . ?
N8 O4 1.232(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
C4 C5 C6 118.5(3) . . ?
C4 C5 N1 116.6(2) . . ?
C6 C5 N1 124.8(3) . . ?
C3 C4 C5 121.1(3) . . ?
C17 C16 C21 119.2(3) . . ?
C17 C16 N6 115.4(3) . . ?
C21 C16 N6 125.4(3) . . ?
N1 C8 N2 113.6(3) . . ?
N1 C8 S2 128.6(2) . . ?
N2 C8 S2 117.9(2) . . ?
C7 C2 C3 121.7(3) . . ?
C7 C2 N7 118.8(3) . . ?
C3 C2 N7 119.5(3) . . ?
N6 C15 N5 112.4(3) . . ?
N6 C15 S1 127.6(2) . . ?
N5 C15 S1 120.0(2) . . ?
C2 C3 C4 118.7(3) . . ?
N3 C9 C10 117.2(3) . . ?
N3 C9 C11 124.7(3) . . ?
C10 C9 C11 118.1(3) . . ?
C2 C7 C6 119.2(3) . . ?
C7 C6 C5 120.7(3) . . ?
C16 C21 C20 120.0(3) . . ?
N4 C14 C12 125.3(3) . . ?
N4 C14 C13 116.1(3) . . ?
C12 C14 C13 118.6(3) . . ?
C20 C19 C18 121.8(3) . . ?
C20 C19 N8 119.4(3) . . ?
C18 C19 N8 118.9(4) . . ?
C18 C17 C16 120.8(3) . . ?
C19 C18 C17 118.9(3) . . ?
C19 C20 C21 119.2(3) . . ?
C8 N1 C5 131.5(2) . . ?
C15 N6 C16 132.6(3) . . ?
C8 N2 N3 121.6(2) . . ?
C15 N5 N4 120.4(2) . . ?
O1 N7 O2 122.6(3) . . ?
O1 N7 C2 119.1(3) . . ?
O2 N7 C2 118.3(3) . . ?
C9 N3 N2 117.4(3) . . ?
C14 N4 N5 117.6(3) . . ?
O3 N8 O4 124.1(3) . . ?
O3 N8 C19 118.2(4) . . ?
O4 N8 C19 117.8(4) . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_corr
_database_code_depnum_ccdc_archive 'CCDC 1584980'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-07 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         'C20 H22 N8 Ni O4 S2, 2(C3 H7 N O)'
_chemical_formula_sum            'C26 H36 N10 Ni O6 S2'
_chemical_formula_weight         707.46

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'
Ni Ni 0.3393 1.1124 '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                   27.826(3)
_cell_length_b                   7.8808(7)
_cell_length_c                   17.1929(15)
_cell_angle_alpha                90
_cell_angle_beta                 118.580(7)
_cell_angle_gamma                90
_cell_volume                     3310.8(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1571
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      19.63

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             1480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.767
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8506
_diffrn_reflns_av_unetI/netI     0.0963
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.667
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             2907
_reflns_number_gt                1616
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0100P)²+0.3000P] 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         2907
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.0776
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_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
Ni1 Ni 0.0000 -0.01388(7) 0.2500 0.0521(3) Uani 1 2 d S T P . .
S1 S 0.03598(4) -0.19753(10) 0.20006(8) 0.0612(4) Uani 1 1 d . . . . .
C4 C 0.05817(14) -0.0479(4) 0.1495(3) 0.0490(12) Uani 1 1 d . . . . .
C5 C 0.11292(16) -0.0187(5) 0.0696(3) 0.0530(12) Uani 1 1 d . . . . .
C3 C -0.02589(15) 0.2745(5) 0.1311(3) 0.0487(12) Uani 1 1 d . . . . .
C6 C 0.15365(17) -0.0980(5) 0.0574(3) 0.0645(14) Uani 1 1 d . . . . .
H6 H 0.1661 -0.2045 0.0822 0.077 Uiso 1 1 calc R U . . .
C8 C 0.15663(17) 0.1338(6) -0.0281(3) 0.0586(13) Uani 1 1 d . . . . .
C2 C -0.01909(14) 0.3827(4) 0.0649(3) 0.0649(13) Uani 1 1 d . . . . .
H2A H 0.0159 0.4378 0.0934 0.097 Uiso 1 1 calc R U . . .
H2B H -0.0475 0.4666 0.0413 0.097 Uiso 1 1 calc R U . . .
H2C H -0.0213 0.3124 0.0176 0.097 Uiso 1 1 calc R U . . .
C7 C 0.17575(16) -0.0228(5) 0.0098(3) 0.0695(14) Uani 1 1 d . . . . .
H7 H 0.2033 -0.0768 0.0032 0.083 Uiso 1 1 calc R U . . .
C10 C 0.09390(16) 0.1387(5) 0.0284(3) 0.0710(15) Uani 1 1 d . . . . .
H10 H 0.0662 0.1942 0.0340 0.085 Uiso 1 1 calc R U . . .
C13 C 0.22292(15) 0.3227(5) 0.2007(3) 0.0792(15) Uani 1 1 d . . . . .
H13A H 0.2152 0.4092 0.1570 0.119 Uiso 1 1 calc R U . . .
H13B H 0.2167 0.2131 0.1732 0.119 Uiso 1 1 calc R U . . .
H13C H 0.2604 0.3315 0.2459 0.119 Uiso 1 1 calc R U . . .
C9 C 0.11563(18) 0.2115(5) -0.0198(3) 0.0776(15) Uani 1 1 d . . . . .
H9 H 0.1023 0.3154 -0.0474 0.093 Uiso 1 1 calc R U . . .
C12 C 0.19128(15) 0.2221(5) 0.3054(3) 0.0948(18) Uani 1 1 d . . . . .
H12A H 0.1705 0.2617 0.3331 0.142 Uiso 1 1 calc R U . . .
H12B H 0.2289 0.2086 0.3494 0.142 Uiso 1 1 calc R U . . .
H12C H 0.1770 0.1150 0.2772 0.142 Uiso 1 1 calc R U . . .
C11 C 0.15068(17) 0.4678(5) 0.2125(3) 0.0769(16) Uani 1 1 d . . . . .
H11 H 0.1286 0.4767 0.2393 0.092 Uiso 1 1 calc R U . . .
C1 C -0.07000(14) 0.3233(4) 0.1525(3) 0.0706(14) Uani 1 1 d . . . . .
H1A H -0.0775 0.2299 0.1809 0.106 Uiso 1 1 calc R U . . .
H1B H -0.1025 0.3520 0.0989 0.106 Uiso 1 1 calc R U . . .
H1C H -0.0583 0.4195 0.1916 0.106 Uiso 1 1 calc R U . . .
N2 N 0.04320(12) 0.1107(3) 0.1373(2) 0.0538(10) Uani 1 1 d . . . . .
N1 N 0.00502(12) 0.1420(3) 0.1681(2) 0.0460(9) Uani 1 1 d . . . . .
N3 N 0.09348(13) -0.1037(4) 0.1202(2) 0.0560(10) Uani 1 1 d . . . . .
H3 H 0.1053 -0.2056 0.1353 0.067 Uiso 1 1 calc R U . . .
N5 N 0.18749(14) 0.3443(4) 0.2399(2) 0.0619(11) Uani 1 1 d . . . . .
N4 N 0.18047(16) 0.2162(6) -0.0775(3) 0.0809(14) Uani 1 1 d . . . . .
O3 O 0.14333(12) 0.5718(3) 0.1543(2) 0.0895(12) Uani 1 1 d . . . . .
O1 O 0.16884(12) 0.3669(4) -0.0980(2) 0.1038(13) Uani 1 1 d . . . . .
O2 O 0.21223(14) 0.1389(4) -0.0939(3) 0.1065(13) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N1 1.923(3) 2 ?
Ni1 N1 1.923(3) . ?
Ni1 S1 2.1579(11) . ?
Ni1 S1 2.1580(11) 2 ?
S1 C4 1.744(4) . ?
C4 N2 1.302(4) . ?
C4 N3 1.373(5) . ?
C5 C6 1.396(5) . ?
C5 N3 1.396(5) . ?
C5 C10 1.401(5) . ?
C3 N1 1.308(4) . ?
C3 C1 1.491(5) . ?
C3 C2 1.505(5) . ?
C6 C7 1.371(5) . ?
C8 C9 1.361(5) . ?
C8 C7 1.378(5) . ?
C8 N4 1.457(6) . ?
C10 C9 1.364(5) . ?
C13 N5 1.445(5) . ?
C12 N5 1.448(5) . ?
C11 O3 1.232(5) . ?
C11 N5 1.325(4) . ?
N2 N1 1.417(4) . ?
N4 O2 1.212(4) . ?
N4 O1 1.237(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
N1 Ni1 N1 100.63(18) 2 . ?
N1 Ni1 S1 158.37(9) 2 . ?
N1 Ni1 S1 85.81(10) . . ?
N1 Ni1 S1 85.81(10) 2 2 ?
N1 Ni1 S1 158.37(9) . 2 ?
S1 Ni1 S1 95.76(6) . 2 ?
C4 S1 Ni1 95.00(14) . . ?
N2 C4 N3 118.6(4) . . ?
N2 C4 S1 124.5(4) . . ?
N3 C4 S1 116.9(3) . . ?
C6 C5 N3 117.6(4) . . ?
C6 C5 C10 117.3(5) . . ?
N3 C5 C10 125.1(4) . . ?
N1 C3 C1 120.9(4) . . ?
N1 C3 C2 121.9(4) . . ?
C1 C3 C2 117.2(3) . . ?
C7 C6 C5 121.6(4) . . ?
C9 C8 C7 120.4(5) . . ?
C9 C8 N4 119.9(4) . . ?
C7 C8 N4 119.6(5) . . ?
C6 C7 C8 119.2(4) . . ?
C9 C10 C5 120.6(4) . . ?
C8 C9 C10 120.8(4) . . ?
O3 C11 N5 125.2(5) . . ?
C4 N2 N1 110.2(3) . . ?
C3 N1 N2 113.2(3) . . ?
C3 N1 Ni1 127.2(3) . . ?
N2 N1 Ni1 119.5(2) . . ?
C4 N3 C5 129.3(3) . . ?
C11 N5 C13 120.3(4) . . ?
C11 N5 C12 121.4(4) . . ?
C13 N5 C12 118.2(3) . . ?
O2 N4 O1 122.5(5) . . ?
O2 N4 C8 119.8(4) . . ?
O1 N4 C8 117.6(5) . . ?

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1819881'
_audit_update_record             
;
2018-01-27 deposited with the CCDC.
2018-03-07 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 H28 N6 Ni O2 S2, 2(C3 H7 N O)'
_chemical_formula_sum            'C28 H42 N8 Ni O4 S2'
_chemical_formula_weight         677.52

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'
Ni Ni 0.3393 1.1124 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.313(2)
_cell_length_b                   15.265(2)
_cell_length_c                   16.704(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.042(10)
_cell_angle_gamma                90
_cell_volume                     3428.7(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3625
_cell_measurement_theta_min      2.67
_cell_measurement_theta_max      19.90

_exptl_crystal_description       Block
_exptl_crystal_colour            Blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.731
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.832
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27431
_diffrn_reflns_av_unetI/netI     0.0670
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.622
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             5970
_reflns_number_gt                3326
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0500P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5970
_refine_ls_number_parameters     406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1047
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1226
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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
Ni1 Ni 0.22557(3) 0.72586(3) 0.24449(3) 0.05531(18) Uani 1 1 d . . . . .
S1 S 0.33516(7) 0.62573(5) 0.29438(6) 0.0629(3) Uani 1 1 d . . . . .
S2 S 0.10980(7) 0.63221(6) 0.18822(7) 0.0687(3) Uani 1 1 d . . . . .
C7 C 0.0172(3) 0.7111(2) 0.1476(2) 0.0541(9) Uani 1 1 d . . . . .
C14 C 0.4330(3) 0.6997(2) 0.3362(2) 0.0539(9) Uani 1 1 d . . . . .
C4 C -0.1666(3) 0.7274(2) 0.0793(2) 0.0578(9) Uani 1 1 d . . . . .
N6 N 0.5256(2) 0.6656(2) 0.3556(2) 0.0637(9) Uani 1 1 d . . . . .
C13 C 0.2989(3) 0.8683(2) 0.3640(2) 0.0583(10) Uani 1 1 d . . . . .
C15 C 0.6181(3) 0.7038(2) 0.4026(2) 0.0564(10) Uani 1 1 d . . . . .
C8 C 0.1636(3) 0.8753(2) 0.1324(2) 0.0538(9) Uani 1 1 d . . . . .
C17 C 0.7953(3) 0.6973(2) 0.4424(2) 0.0676(11) Uani 1 1 d . . . . .
H17 H 0.8516 0.6704 0.4380 0.081 Uiso 1 1 calc R U . . .
C20 C 0.6292(3) 0.7740(2) 0.4579(2) 0.0716(11) Uani 1 1 d . . . . .
H20 H 0.5733 0.8003 0.4637 0.086 Uiso 1 1 calc R U . . .
C3 C -0.2549(3) 0.6956(2) 0.0852(2) 0.0673(10) Uani 1 1 d . . . . .
H3 H -0.2539 0.6467 0.1188 0.081 Uiso 1 1 calc R U . . .
C5 C -0.1710(3) 0.7995(3) 0.0284(2) 0.0741(11) Uani 1 1 d . . . . .
H5 H -0.1130 0.8214 0.0228 0.089 Uiso 1 1 calc R U . . .
C1 C -0.3463(3) 0.8089(3) -0.0060(2) 0.0643(10) Uani 1 1 d . . . . .
C12 C 0.3780(3) 0.9205(2) 0.4269(2) 0.0774(12) Uani 1 1 d . . . . .
H12A H 0.4177 0.8828 0.4717 0.116 Uiso 1 1 calc R U . . .
H12B H 0.3481 0.9652 0.4506 0.116 Uiso 1 1 calc R U . . .
H12C H 0.4194 0.9473 0.3992 0.116 Uiso 1 1 calc R U . . .
C16 C 0.7030(3) 0.6667(2) 0.3957(2) 0.0643(10) Uani 1 1 d . . . . .
H16 H 0.6973 0.6200 0.3586 0.077 Uiso 1 1 calc R U . . .
C18 C 0.8053(3) 0.7680(2) 0.4963(2) 0.0600(10) Uani 1 1 d . . . . .
C19 C 0.7226(3) 0.8051(2) 0.5043(2) 0.0691(11) Uani 1 1 d . . . . .
H19 H 0.7290 0.8519 0.5414 0.083 Uiso 1 1 calc R U . . .
C6 C -0.2607(3) 0.8395(2) -0.0140(2) 0.0720(11) Uani 1 1 d . . . . .
H6 H -0.2627 0.8878 -0.0485 0.086 Uiso 1 1 calc R U . . .
C9 C 0.0883(3) 0.9306(2) 0.0685(2) 0.0704(11) Uani 1 1 d . . . . .
H9A H 0.0542 0.8960 0.0191 0.106 Uiso 1 1 calc R U . . .
H9B H 0.1211 0.9788 0.0523 0.106 Uiso 1 1 calc R U . . .
H9C H 0.0413 0.9525 0.0929 0.106 Uiso 1 1 calc R U . . .
C10 C 0.2696(3) 0.8983(2) 0.1499(2) 0.0684(11) Uani 1 1 d . . . . .
H10A H 0.2845 0.9526 0.1808 0.103 Uiso 1 1 calc R U . . .
H10B H 0.2816 0.9045 0.0971 0.103 Uiso 1 1 calc R U . . .
H10C H 0.3114 0.8528 0.1833 0.103 Uiso 1 1 calc R U . . .
C2 C -0.3429(3) 0.7355(3) 0.0422(2) 0.0721(11) Uani 1 1 d . . . . .
H2 H -0.4017 0.7126 0.0456 0.087 Uiso 1 1 calc R U . . .
C11 C 0.1947(3) 0.8940(2) 0.3499(2) 0.0780(12) Uani 1 1 d . . . . .
H11A H 0.1506 0.8498 0.3167 0.117 Uiso 1 1 calc R U . . .
H11B H 0.1807 0.9488 0.3201 0.117 Uiso 1 1 calc R U . . .
H11C H 0.1853 0.8999 0.4039 0.117 Uiso 1 1 calc R U . . .
N5 N 0.4206(2) 0.78195(17) 0.34849(17) 0.0581(8) Uani 1 1 d . . . . .
N3 N 0.1389(2) 0.80859(16) 0.16767(17) 0.0512(7) Uani 1 1 d . . . . .
N4 N 0.3182(2) 0.80209(17) 0.32429(17) 0.0543(7) Uani 1 1 d . . . . .
N2 N 0.0359(2) 0.79347(18) 0.13970(17) 0.0581(8) Uani 1 1 d . . . . .
N1 N -0.0777(3) 0.6823(2) 0.1230(2) 0.0655(10) Uani 1 1 d . . . . .
O2 O 0.9012(2) 0.79509(17) 0.53947(17) 0.0781(8) Uani 1 1 d . . . . .
O1 O -0.4389(2) 0.84528(19) -0.04392(18) 0.0892(8) Uani 1 1 d . . . . .
C22 C 0.9205(4) 0.8044(3) 0.3114(3) 0.1228(18) Uani 1 1 d . . . . .
H22A H 0.8562 0.7845 0.3098 0.184 Uiso 1 1 calc R U . . .
H22B H 0.9702 0.7843 0.3629 0.184 Uiso 1 1 calc R U . . .
H22C H 0.9343 0.7816 0.2631 0.184 Uiso 1 1 calc R U . . .
C23 C 0.9035(4) 0.9441(3) 0.3786(3) 0.1285(19) Uani 1 1 d . . . . .
H23A H 0.9575 0.9329 0.4306 0.193 Uiso 1 1 calc R U . . .
H23B H 0.8426 0.9233 0.3838 0.193 Uiso 1 1 calc R U . . .
H23C H 0.8986 1.0059 0.3674 0.193 Uiso 1 1 calc R U . . .
C24 C 0.9361(3) 0.9427(3) 0.2468(2) 0.0681(11) Uani 1 1 d . . . . .
H24 H 0.9476 0.9101 0.2041 0.082 Uiso 1 1 calc R U . . .
N7 N 0.9215(2) 0.8990(2) 0.3091(2) 0.0742(9) Uani 1 1 d . . . . .
O3 O 0.9358(2) 1.02134(18) 0.24013(18) 0.0914(9) Uani 1 1 d . . . . .
C25 C -0.4467(3) 0.9170(3) -0.0995(3) 0.1244(18) Uani 1 1 d . . . . .
H25A H -0.4120 0.9665 -0.0675 0.187 Uiso 1 1 calc R U . . .
H25B H -0.5155 0.9317 -0.1271 0.187 Uiso 1 1 calc R U . . .
H25C H -0.4179 0.9015 -0.1417 0.187 Uiso 1 1 calc R U . . .
C26 C 0.9145(3) 0.8626(3) 0.6002(3) 0.1003(15) Uani 1 1 d . . . . .
H26A H 0.8825 0.9150 0.5722 0.151 Uiso 1 1 calc R U . . .
H26B H 0.9842 0.8735 0.6279 0.151 Uiso 1 1 calc R U . . .
H26C H 0.8857 0.8452 0.6419 0.151 Uiso 1 1 calc R U . . .
N8 N 0.3955(3) 0.0912(2) 0.7719(2) 0.0775(9) Uani 1 1 d . . . . .
C30 C 0.3299(3) 0.0630(3) 0.8146(3) 0.1183(17) Uani 1 1 d . . . . .
H30A H 0.2988 0.0089 0.7901 0.177 Uiso 1 1 calc R U . . .
H30B H 0.2797 0.1067 0.8086 0.177 Uiso 1 1 calc R U . . .
H30C H 0.3669 0.0543 0.8740 0.177 Uiso 1 1 calc R U . . .
C31 C 0.4473(3) 0.1725(3) 0.8013(3) 0.1159(17) Uani 1 1 d . . . . .
H31A H 0.4929 0.1834 0.7716 0.174 Uiso 1 1 calc R U . . .
H31B H 0.4834 0.1687 0.8614 0.174 Uiso 1 1 calc R U . . .
H31C H 0.4001 0.2196 0.7905 0.174 Uiso 1 1 calc R U . . .
O4 O 0.3682(3) -0.0221(2) 0.6826(2) 0.1348(14) Uani 1 1 d . . . . .
C29 C 0.4092(3) 0.0460(3) 0.7105(3) 0.0931(14) Uani 1 1 d . . . . .
H29 H 0.4540 0.0681 0.6864 0.112 Uiso 1 1 calc R U . . .
H1A H -0.084(3) 0.637(2) 0.139(2) 0.061(13) Uiso 1 1 d . . . . .
H6A H 0.531(2) 0.6221(19) 0.335(2) 0.054(12) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ni1 N4 1.918(3) . ?
Ni1 N3 1.921(3) . ?
Ni1 S1 2.1436(10) . ?
Ni1 S2 2.1461(11) . ?
S1 C14 1.748(4) . ?
S2 C7 1.747(3) . ?
C7 N2 1.301(4) . ?
C7 N1 1.352(4) . ?
C14 N5 1.294(4) . ?
C14 N6 1.355(4) . ?
C4 C5 1.379(4) . ?
C4 C3 1.389(4) . ?
C4 N1 1.410(5) . ?
N6 C15 1.413(4) . ?
C13 N4 1.289(4) . ?
C13 C11 1.481(5) . ?
C13 C12 1.485(5) . ?
C15 C16 1.380(4) . ?
C15 C20 1.389(4) . ?
C8 N3 1.285(4) . ?
C8 C10 1.487(4) . ?
C8 C9 1.491(4) . ?
C17 C16 1.366(4) . ?
C17 C18 1.381(5) . ?
C20 C19 1.378(5) . ?
C3 C2 1.362(5) . ?
C5 C6 1.379(5) . ?
C1 C6 1.360(5) . ?
C1 C2 1.371(5) . ?
C1 O1 1.375(4) . ?
C18 C19 1.360(5) . ?
C18 O2 1.377(4) . ?
N5 N4 1.414(3) . ?
N3 N2 1.405(3) . ?
O2 C26 1.413(4) . ?
O1 C25 1.415(4) . ?
C22 N7 1.445(4) . ?
C23 N7 1.445(5) . ?
C24 O3 1.206(4) . ?
C24 N7 1.310(4) . ?
N8 C29 1.305(5) . ?
N8 C30 1.428(4) . ?
N8 C31 1.443(4) . ?
O4 C29 1.206(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
N4 Ni1 N3 101.53(11) . . ?
N4 Ni1 S1 85.57(9) . . ?
N3 Ni1 S1 161.36(8) . . ?
N4 Ni1 S2 162.72(8) . . ?
N3 Ni1 S2 85.44(9) . . ?
S1 Ni1 S2 92.73(4) . . ?
C14 S1 Ni1 94.25(12) . . ?
C7 S2 Ni1 94.57(13) . . ?
N2 C7 N1 120.2(3) . . ?
N2 C7 S2 123.5(3) . . ?
N1 C7 S2 116.3(3) . . ?
N5 C14 N6 120.7(3) . . ?
N5 C14 S1 123.8(3) . . ?
N6 C14 S1 115.6(3) . . ?
C5 C4 C3 118.2(4) . . ?
C5 C4 N1 123.5(4) . . ?
C3 C4 N1 118.3(4) . . ?
C14 N6 C15 128.9(3) . . ?
N4 C13 C11 120.5(4) . . ?
N4 C13 C12 122.6(3) . . ?
C11 C13 C12 116.9(3) . . ?
C16 C15 C20 117.9(4) . . ?
C16 C15 N6 118.0(3) . . ?
C20 C15 N6 124.0(3) . . ?
N3 C8 C10 121.3(3) . . ?
N3 C8 C9 122.2(3) . . ?
C10 C8 C9 116.5(3) . . ?
C16 C17 C18 120.2(3) . . ?
C19 C20 C15 120.5(4) . . ?
C2 C3 C4 120.4(4) . . ?
C6 C5 C4 120.6(4) . . ?
C6 C1 C2 119.1(4) . . ?
C6 C1 O1 125.0(4) . . ?
C2 C1 O1 115.8(4) . . ?
C17 C16 C15 121.3(4) . . ?
C19 C18 O2 124.7(4) . . ?
C19 C18 C17 119.3(4) . . ?
O2 C18 C17 116.0(3) . . ?
C18 C19 C20 120.7(4) . . ?
C1 C6 C5 120.6(4) . . ?
C3 C2 C1 121.0(4) . . ?
C14 N5 N4 110.5(3) . . ?
C8 N3 N2 113.5(3) . . ?
C8 N3 Ni1 127.7(3) . . ?
N2 N3 Ni1 118.6(2) . . ?
C13 N4 N5 114.0(3) . . ?
C13 N4 Ni1 127.9(3) . . ?
N5 N4 Ni1 118.0(2) . . ?
C7 N2 N3 110.7(3) . . ?
C7 N1 C4 129.3(3) . . ?
C18 O2 C26 117.3(3) . . ?
C1 O1 C25 117.5(3) . . ?
O3 C24 N7 125.7(4) . . ?
C24 N7 C22 122.4(4) . . ?
C24 N7 C23 121.1(3) . . ?
C22 N7 C23 116.6(3) . . ?
C29 N8 C30 122.4(4) . . ?
C29 N8 C31 121.6(4) . . ?
C30 N8 C31 116.0(4) . . ?
O4 C29 N8 125.1(5) . . ?

_refine_diff_density_max         0.199
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_arup
_database_code_depnum_ccdc_archive 'CCDC 1819882'
_audit_update_record             
;
2018-01-27 deposited with the CCDC.
2018-03-07 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 H28 N6 O2 S2 Zn, C3 H7 N O'
_chemical_formula_sum            'C25 H35 N7 O3 S2 Zn'
_chemical_formula_weight         611.09

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

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

_cell_length_a                   7.8976(8)
_cell_length_b                   11.1979(11)
_cell_length_c                   17.2554(16)
_cell_angle_alpha                98.130(8)
_cell_angle_beta                 92.775(8)
_cell_angle_gamma                91.666(8)
_cell_volume                     1507.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1173
_cell_measurement_theta_min      3.28
_cell_measurement_theta_max      20.63

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             640
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.991
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.57796
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
__audit_creation_method          'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9861
_diffrn_reflns_av_unetI/netI     0.1526
_diffrn_reflns_av_R_equivalents  0.0607
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.117
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_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 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5344
_reflns_number_gt                2354
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0100P)²+0.0200P] 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         5344
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1739
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.0814
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
Zn1 Zn 0.26560(9) 0.74969(5) 0.24021(5) 0.0628(3) Uani 1 1 d . . . . .
S2 S 0.3776(2) 0.56364(12) 0.21820(11) 0.0636(5) Uani 1 1 d . . . . .
S1 S 0.3978(2) 0.92482(12) 0.21966(11) 0.0685(6) Uani 1 1 d . . . . .
N3 N 0.0584(6) 0.8029(4) 0.1810(3) 0.0535(15) Uani 1 1 d . . . . .
C8 C 0.2153(7) 0.9722(5) 0.1707(3) 0.0486(17) Uani 1 1 d . . . . .
N5 N 0.2553(6) 0.5951(4) 0.3669(3) 0.0583(15) Uani 1 1 d . . . . .
N2 N 0.0704(6) 0.9169(4) 0.1556(3) 0.0532(15) Uani 1 1 d . . . . .
N1 N 0.2407(7) 1.0839(5) 0.1471(4) 0.0565(17) Uani 1 1 d . . . . .
O3 O 0.5561(6) 0.2426(4) 0.2026(3) 0.0833(17) Uani 1 1 d . . . . .
N4 N 0.2184(6) 0.7101(4) 0.3506(3) 0.0560(15) Uani 1 1 d . . . . .
C15 C 0.3244(7) 0.5286(5) 0.3102(4) 0.0543(18) Uani 1 1 d . . . . .
N6 N 0.3680(7) 0.4131(5) 0.3215(4) 0.0628(17) Uani 1 1 d . . . . .
C9 C -0.0817(8) 0.7431(5) 0.1593(4) 0.0573(19) Uani 1 1 d . . . . .
C5 C 0.1246(8) 1.1539(5) 0.1094(4) 0.0503(17) Uani 1 1 d . . . . .
C18 C 0.4032(8) 0.1706(6) 0.4414(5) 0.074(2) Uani 1 1 d . . . . .
H18 H 0.4341 0.0904 0.4344 0.089 Uiso 1 1 calc R U . . .
C3 C 0.0719(9) 1.3483(5) 0.0701(4) 0.070(2) Uani 1 1 d . . . . .
H3 H 0.1079 1.4275 0.0679 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1751(8) 1.2725(5) 0.1048(3) 0.0576(19) Uani 1 1 d . . . . .
H4 H 0.2817 1.3012 0.1257 0.069 Uiso 1 1 calc R U . . .
N7 N 0.8161(7) 0.2463(5) 0.2674(3) 0.0681(17) Uani 1 1 d . . . . .
O1 O -0.1861(6) 1.3878(3) 0.0068(3) 0.0866(17) Uani 1 1 d . . . . .
C6 C -0.0331(8) 1.1126(5) 0.0772(4) 0.0594(19) Uani 1 1 d . . . . .
H6 H -0.0684 1.0330 0.0784 0.071 Uiso 1 1 calc R U . . .
C17 C 0.4024(7) 0.2334(5) 0.3786(4) 0.067(2) Uani 1 1 d . . . . .
H17 H 0.4296 0.1952 0.3296 0.080 Uiso 1 1 calc R U . . .
C11 C -0.1074(7) 0.6210(4) 0.1825(4) 0.079(2) Uani 1 1 d . . . . .
H11A H -0.0117 0.6037 0.2151 0.119 Uiso 1 1 calc R U . . .
H11B H -0.1184 0.5617 0.1364 0.119 Uiso 1 1 calc R U . . .
H11C H -0.2085 0.6189 0.2111 0.119 Uiso 1 1 calc R U . . .
C13 C 0.1639(8) 0.7817(6) 0.4084(5) 0.069(2) Uani 1 1 d . . . . .
C10 C -0.2238(7) 0.7930(5) 0.1151(4) 0.080(2) Uani 1 1 d . . . . .
H10A H -0.2521 0.8699 0.1425 0.121 Uiso 1 1 calc R U . . .
H10B H -0.3210 0.7385 0.1109 0.121 Uiso 1 1 calc R U . . .
H10C H -0.1898 0.8026 0.0636 0.121 Uiso 1 1 calc R U . . .
O2 O 0.3598(7) 0.1473(4) 0.5715(4) 0.1040(19) Uani 1 1 d . . . . .
C16 C 0.3607(8) 0.3548(5) 0.3883(4) 0.0554(18) Uani 1 1 d . . . . .
C12 C 0.1192(8) 0.9084(5) 0.3984(4) 0.093(3) Uani 1 1 d . . . . .
H12A H 0.1402 0.9221 0.3459 0.139 Uiso 1 1 calc R U . . .
H12B H 0.1873 0.9646 0.4351 0.139 Uiso 1 1 calc R U . . .
H12C H 0.0014 0.9195 0.4077 0.139 Uiso 1 1 calc R U . . .
C14 C 0.1447(9) 0.7457(6) 0.4874(4) 0.097(3) Uani 1 1 d . . . . .
H14A H 0.0666 0.6775 0.4833 0.146 Uiso 1 1 calc R U . . .
H14B H 0.1022 0.8119 0.5217 0.146 Uiso 1 1 calc R U . . .
H14C H 0.2529 0.7245 0.5082 0.146 Uiso 1 1 calc R U . . .
C2 C -0.0857(9) 1.3060(5) 0.0386(4) 0.0614(19) Uani 1 1 d . . . . .
C20 C 0.3163(10) 0.2004(6) 0.6451(5) 0.109(3) Uani 1 1 d . . . . .
H20A H 0.3982 0.2636 0.6652 0.163 Uiso 1 1 calc R U . . .
H20B H 0.3146 0.1407 0.6799 0.163 Uiso 1 1 calc R U . . .
H20C H 0.2061 0.2336 0.6412 0.163 Uiso 1 1 calc R U . . .
C1 C -0.3554(9) 1.3540(5) -0.0167(4) 0.095(3) Uani 1 1 d . . . . .
H1A H -0.3587 1.2840 -0.0560 0.142 Uiso 1 1 calc R U . . .
H1B H -0.4088 1.4192 -0.0378 0.142 Uiso 1 1 calc R U . . .
H1C H -0.4146 1.3356 0.0277 0.142 Uiso 1 1 calc R U . . .
C7 C -0.1390(8) 1.1884(5) 0.0431(4) 0.0629(19) Uani 1 1 d . . . . .
H7 H -0.2466 1.1605 0.0231 0.076 Uiso 1 1 calc R U . . .
C23 C 0.9583(10) 0.1802(7) 0.2920(5) 0.162(4) Uani 1 1 d . . . . .
H23A H 0.9345 0.0952 0.2773 0.244 Uiso 1 1 calc R U . . .
H23B H 0.9772 0.1978 0.3479 0.244 Uiso 1 1 calc R U . . .
H23C H 1.0577 0.2036 0.2672 0.244 Uiso 1 1 calc R U . . .
C19 C 0.3602(9) 0.2223(7) 0.5139(5) 0.075(2) Uani 1 1 d . . . . .
C22 C 0.6853(11) 0.1973(8) 0.2257(5) 0.115(3) Uani 1 1 d . . . . .
H22 H 0.6899 0.1144 0.2107 0.138 Uiso 1 1 calc R U . . .
C24 C 0.3199(9) 0.3422(6) 0.5252(4) 0.084(2) Uani 1 1 d . . . . .
H24 H 0.2934 0.3797 0.5745 0.101 Uiso 1 1 calc R U . . .
C25 C 0.8298(11) 0.3711(6) 0.2893(6) 0.183(5) Uani 1 1 d . . . . .
H25A H 0.7662 0.4100 0.2518 0.274 Uiso 1 1 calc R U . . .
H25B H 0.9468 0.3974 0.2910 0.274 Uiso 1 1 calc R U . . .
H25C H 0.7858 0.3917 0.3402 0.274 Uiso 1 1 calc R U . . .
C26 C 0.3192(9) 0.4066(6) 0.4616(5) 0.075(2) Uani 1 1 d . . . . .
H26 H 0.2899 0.4871 0.4691 0.090 Uiso 1 1 calc R U . . .
H6A H 0.401(7) 0.377(4) 0.278(3) 0.07(2) Uiso 1 1 d . . . . .
H1K H 0.327(6) 1.112(4) 0.162(3) 0.06(2) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Zn1 N3 2.035(5) . ?
Zn1 N4 2.065(5) . ?
Zn1 S1 2.2748(17) . ?
Zn1 S2 2.2766(15) . ?
S2 C15 1.755(7) . ?
S1 C8 1.768(6) . ?
N3 C9 1.288(6) . ?
N3 N2 1.409(5) . ?
C8 N2 1.282(6) . ?
C8 N1 1.382(7) . ?
N5 C15 1.295(7) . ?
N5 N4 1.393(5) . ?
N1 C5 1.417(7) . ?
O3 C22 1.227(9) . ?
N4 C13 1.287(7) . ?
C15 N6 1.386(7) . ?
N6 C16 1.407(8) . ?
C9 C11 1.490(7) . ?
C9 C10 1.492(7) . ?
C5 C6 1.379(7) . ?
C5 C4 1.389(6) . ?
C18 C19 1.365(9) . ?
C18 C17 1.373(8) . ?
C3 C4 1.371(7) . ?
C3 C2 1.377(7) . ?
N7 C22 1.292(8) . ?
N7 C25 1.394(7) . ?
N7 C23 1.443(7) . ?
O1 C2 1.382(6) . ?
O1 C1 1.404(6) . ?
C6 C7 1.379(7) . ?
C17 C16 1.397(7) . ?
C13 C14 1.489(8) . ?
C13 C12 1.504(7) . ?
O2 C20 1.388(8) . ?
O2 C19 1.389(8) . ?
C16 C26 1.373(8) . ?
C2 C7 1.385(7) . ?
C19 C24 1.378(8) . ?
C24 C26 1.396(8) . ?

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
N3 Zn1 N4 113.9(2) . . ?
N3 Zn1 S1 87.09(14) . . ?
N4 Zn1 S1 122.91(14) . . ?
N3 Zn1 S2 125.20(13) . . ?
N4 Zn1 S2 86.26(13) . . ?
S1 Zn1 S2 125.13(7) . . ?
C15 S2 Zn1 92.8(2) . . ?
C8 S1 Zn1 92.6(2) . . ?
C9 N3 N2 114.3(5) . . ?
C9 N3 Zn1 128.5(4) . . ?
N2 N3 Zn1 117.0(3) . . ?
N2 C8 N1 119.1(5) . . ?
N2 C8 S1 128.6(5) . . ?
N1 C8 S1 112.3(4) . . ?
C15 N5 N4 113.8(5) . . ?
C8 N2 N3 114.7(5) . . ?
C8 N1 C5 129.3(6) . . ?
C13 N4 N5 115.1(6) . . ?
C13 N4 Zn1 127.4(5) . . ?
N5 N4 Zn1 117.5(4) . . ?
N5 C15 N6 117.9(6) . . ?
N5 C15 S2 129.4(5) . . ?
N6 C15 S2 112.7(5) . . ?
C15 N6 C16 130.4(6) . . ?
N3 C9 C11 118.8(6) . . ?
N3 C9 C10 123.0(5) . . ?
C11 C9 C10 118.1(6) . . ?
C6 C5 C4 118.3(6) . . ?
C6 C5 N1 124.7(6) . . ?
C4 C5 N1 117.0(6) . . ?
C19 C18 C17 122.0(7) . . ?
C4 C3 C2 119.3(6) . . ?
C3 C4 C5 121.7(6) . . ?
C22 N7 C25 120.5(7) . . ?
C22 N7 C23 124.1(7) . . ?
C25 N7 C23 115.4(7) . . ?
C2 O1 C1 118.8(5) . . ?
C7 C6 C5 120.5(6) . . ?
C18 C17 C16 120.0(7) . . ?
N4 C13 C14 122.8(6) . . ?
N4 C13 C12 120.2(7) . . ?
C14 C13 C12 116.9(6) . . ?
C20 O2 C19 115.8(6) . . ?
C26 C16 C17 117.8(7) . . ?
C26 C16 N6 126.1(6) . . ?
C17 C16 N6 116.1(6) . . ?
C3 C2 O1 116.7(6) . . ?
C3 C2 C7 119.9(6) . . ?
O1 C2 C7 123.4(6) . . ?
C6 C7 C2 120.2(6) . . ?
C18 C19 C24 119.2(8) . . ?
C18 C19 O2 116.0(7) . . ?
C24 C19 O2 124.8(8) . . ?
O3 C22 N7 130.3(9) . . ?
C19 C24 C26 119.0(7) . . ?
C16 C26 C24 122.0(7) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_corr_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1584979'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-07 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         'C12 H15 N3 O2 S'
_chemical_formula_sum            'C12 H15 N3 O2 S'
_chemical_formula_weight         265.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.662(3)
_cell_length_b                   7.5742(16)
_cell_length_c                   13.561(3)
_cell_angle_alpha                90
_cell_angle_beta                 116.781(7)
_cell_angle_gamma                90
_cell_volume                     1344.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2137
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      21.66

_exptl_crystal_description       Block
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    0.239
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12821
_diffrn_reflns_av_unetI/netI     0.0802
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.556
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             2342
_reflns_number_gt                1703
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0100P)²+0.5000P] 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         2342
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1415
_refine_ls_wR_factor_gt          0.1228
_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
S1 S 0.19580(8) 0.56401(11) 0.00867(8) 0.0906(3) Uani 1 1 d . . . . .
O1 O 0.05621(12) 0.4086(2) 0.40685(13) 0.0582(5) Uani 1 1 d . . . . .
C3 C 0.18712(16) 0.4915(3) 0.36297(18) 0.0476(5) Uani 1 1 d . . . . .
H3 H 0.2061 0.5767 0.4181 0.057 Uiso 1 1 calc R U . . .
C5 C 0.21329(16) 0.3444(3) 0.22074(17) 0.0476(5) Uani 1 1 d . . . . .
C6 C 0.12731(17) 0.2435(3) 0.1965(2) 0.0563(6) Uani 1 1 d . . . . .
H6 H 0.1064 0.1617 0.1394 0.068 Uiso 1 1 calc R U . . .
C4 C 0.24251(16) 0.4725(3) 0.30385(18) 0.0477(6) Uani 1 1 d . . . . .
C7 C 0.07154(18) 0.2616(3) 0.2555(2) 0.0577(6) Uani 1 1 d . . . . .
H7 H 0.0138 0.1927 0.2383 0.069 Uiso 1 1 calc R U . . .
C2 C 0.10295(16) 0.3836(3) 0.34029(18) 0.0478(5) Uani 1 1 d . . . . .
C1 C -0.0280(2) 0.2957(4) 0.3897(2) 0.0702(8) Uani 1 1 d . . . . .
H1A H -0.0811 0.3106 0.3157 0.105 Uiso 1 1 calc R U . . .
H1B H -0.0538 0.3258 0.4412 0.105 Uiso 1 1 calc R U . . .
H1C H -0.0056 0.1750 0.4006 0.105 Uiso 1 1 calc R U . . .
C9 C 0.2711(2) 0.4058(3) 0.0795(2) 0.0611(7) Uani 1 1 d . . . . .
C10 C 0.35484(19) 0.1781(4) 0.1998(2) 0.0644(7) Uani 1 1 d . . . . .
C8 C 0.3734(2) 0.6720(4) 0.4189(2) 0.0719(8) Uani 1 1 d . . . . .
H8A H 0.3286 0.7667 0.4156 0.108 Uiso 1 1 calc R U . . .
H8B H 0.4367 0.7197 0.4260 0.108 Uiso 1 1 calc R U . . .
H8C H 0.3863 0.5984 0.4815 0.108 Uiso 1 1 calc R U . . .
C12 C 0.3113(2) -0.0078(4) 0.1858(3) 0.0817(9) Uani 1 1 d . . . . .
H12A H 0.2574 -0.0216 0.1122 0.123 Uiso 1 1 calc R U . . .
H12B H 0.2848 -0.0268 0.2381 0.123 Uiso 1 1 calc R U . . .
H12C H 0.3643 -0.0921 0.1983 0.123 Uiso 1 1 calc R U . . .
C11 C 0.4393(2) 0.2123(5) 0.3163(3) 0.0910(10) Uani 1 1 d . . . . .
H11A H 0.4934 0.1283 0.3333 0.137 Uiso 1 1 calc R U . . .
H11B H 0.4121 0.2004 0.3684 0.137 Uiso 1 1 calc R U . . .
H11C H 0.4655 0.3296 0.3203 0.137 Uiso 1 1 calc R U . . .
O2 O 0.32673(13) 0.5698(2) 0.32050(14) 0.0615(5) Uani 1 1 d . . . . .
N1 N 0.27482(14) 0.3137(3) 0.16510(15) 0.0527(5) Uani 1 1 d . . . . .
N3 N 0.39602(19) 0.2072(4) 0.1199(2) 0.0824(8) Uani 1 1 d . . . . .
N2 N 0.3512(2) 0.3312(4) 0.0546(2) 0.0817(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C9 1.619(3) . ?
O1 C2 1.370(3) . ?
O1 C1 1.433(3) . ?
C3 C4 1.382(3) . ?
C3 C2 1.394(3) . ?
C5 C6 1.381(3) . ?
C5 C4 1.400(3) . ?
C5 N1 1.432(3) . ?
C6 C7 1.384(3) . ?
C4 O2 1.367(3) . ?
C7 C2 1.383(3) . ?
C9 N1 1.334(3) . ?
C9 N2 1.473(3) . ?
C10 N1 1.468(3) . ?
C10 N3 1.476(4) . ?
C10 C12 1.522(4) . ?
C10 C11 1.527(4) . ?
C8 O2 1.423(3) . ?
N3 N2 1.254(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
C2 O1 C1 117.44(19) . . ?
C4 C3 C2 120.3(2) . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 N1 120.62(19) . . ?
C4 C5 N1 119.98(19) . . ?
C5 C6 C7 121.4(2) . . ?
O2 C4 C3 124.8(2) . . ?
O2 C4 C5 115.64(19) . . ?
C3 C4 C5 119.5(2) . . ?
C2 C7 C6 119.0(2) . . ?
O1 C2 C7 124.2(2) . . ?
O1 C2 C3 115.4(2) . . ?
C7 C2 C3 120.4(2) . . ?
N1 C9 N2 106.0(2) . . ?
N1 C9 S1 130.8(2) . . ?
N2 C9 S1 123.3(2) . . ?
N1 C10 N3 101.1(2) . . ?
N1 C10 C12 112.2(2) . . ?
N3 C10 C12 109.5(2) . . ?
N1 C10 C11 111.8(2) . . ?
N3 C10 C11 108.9(2) . . ?
C12 C10 C11 112.6(3) . . ?
C4 O2 C8 117.69(17) . . ?
C9 N1 C5 125.8(2) . . ?
C9 N1 C10 111.0(2) . . ?
C5 N1 C10 123.14(19) . . ?
N2 N3 C10 111.9(2) . . ?
N3 N2 C9 110.1(2) . . ?

_refine_diff_density_max         0.154
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_Cu(HLnitro)2
_database_code_depnum_ccdc_archive 'CCDC 1572110'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-07 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         'C20 H22 Cu N8 O4 S2, 2(C3 H7 N O)'
_chemical_formula_sum            'C26 H36 Cu N10 O6 S2'
_chemical_formula_weight         712.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   28.1709(13)
_cell_length_b                   7.8227(4)
_cell_length_c                   17.0447(8)
_cell_angle_alpha                90
_cell_angle_beta                 118.540(3)
_cell_angle_gamma                90
_cell_volume                     3299.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1885
_cell_measurement_theta_min      2.72
_cell_measurement_theta_max      19.01

_exptl_crystal_description       Block
_exptl_crystal_colour            Black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_F_000             1484
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.843
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12516
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.646
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.046
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2920
_reflns_number_gt                1693
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0600P)²+0.0200P] 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         2920
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0872
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.0000 1.03253(8) 0.2500 0.0474(3) Uani 1 2 d S T P . .
S1 S 0.04759(4) 1.20821(12) 0.21098(7) 0.0551(3) Uani 1 1 d . . . . .
C4 C 0.05936(15) 1.0531(4) 0.1483(2) 0.0407(9) Uani 1 1 d . . . . .
C8 C 0.15690(16) 0.8516(5) -0.0284(2) 0.0493(10) Uani 1 1 d . . . . .
C5 C 0.11407(15) 1.0137(5) 0.0683(2) 0.0459(10) Uani 1 1 d . . . . .
C6 C 0.09457(16) 0.8544(5) 0.0284(3) 0.0600(12) Uani 1 1 d . . . . .
H6 H 0.0667 0.8021 0.0341 0.072 Uiso 1 1 calc R U . . .
C9 C 0.17600(17) 1.0081(5) 0.0076(3) 0.0586(12) Uani 1 1 d . . . . .
H9 H 0.2032 1.0601 -0.0002 0.070 Uiso 1 1 calc R U . . .
C10 C 0.15457(16) 1.0896(5) 0.0559(3) 0.0542(11) Uani 1 1 d . . . . .
H10 H 0.1675 1.1968 0.0804 0.065 Uiso 1 1 calc R U . . .
C13 C 0.15328(18) 0.5305(6) 0.2124(3) 0.0615(12) Uani 1 1 d . . . . .
H13 H 0.1308 0.5207 0.2382 0.074 Uiso 1 1 calc R U . . .
C11 C 0.22435(17) 0.6826(5) 0.2031(3) 0.0636(12) Uani 1 1 d . . . . .
H11A H 0.2153 0.6038 0.1548 0.095 Uiso 1 1 calc R U . . .
H11B H 0.2610 0.6636 0.2484 0.095 Uiso 1 1 calc R U . . .
H11C H 0.2207 0.7976 0.1812 0.095 Uiso 1 1 calc R U . . .
C12 C 0.19139(18) 0.7792(6) 0.3061(3) 0.0776(14) Uani 1 1 d . . . . .
H12A H 0.1697 0.7399 0.3320 0.116 Uiso 1 1 calc R U . . .
H12B H 0.1782 0.8880 0.2780 0.116 Uiso 1 1 calc R U . . .
H12C H 0.2282 0.7909 0.3520 0.116 Uiso 1 1 calc R U . . .
C7 C 0.11614(17) 0.7742(5) -0.0194(3) 0.0642(13) Uani 1 1 d . . . . .
H7 H 0.1031 0.6680 -0.0454 0.077 Uiso 1 1 calc R U . . .
N3 N 0.09533(12) 1.1018(4) 0.11984(19) 0.0488(8) Uani 1 1 d . . . . .
H3 H 0.1086 1.2026 0.1362 0.059 Uiso 1 1 calc R U . . .
N5 N 0.18854(13) 0.6570(4) 0.2402(2) 0.0514(9) Uani 1 1 d . . . . .
N4 N 0.18063(15) 0.7599(5) -0.0763(2) 0.0622(10) Uani 1 1 d . . . . .
N2 N 0.03749(12) 0.9023(4) 0.1274(2) 0.0460(8) Uani 1 1 d . . . . .
O3 O 0.14763(13) 0.4252(4) 0.1557(2) 0.0762(10) Uani 1 1 d . . . . .
O2 O 0.20999(14) 0.8411(4) -0.0972(2) 0.0864(11) Uani 1 1 d . . . . .
O1 O 0.17082(13) 0.6083(5) -0.0918(2) 0.0853(11) Uani 1 1 d . . . . .
N1 N 0.00002(12) 0.8725(4) 0.15845(19) 0.0432(8) Uani 1 1 d . . . . .
C2 C -0.02861(15) 0.7353(5) 0.1260(2) 0.0471(10) Uani 1 1 d . . . . .
C1 C -0.02226(17) 0.6195(5) 0.0622(3) 0.0634(13) Uani 1 1 d . . . . .
H1A H -0.0196 0.6864 0.0172 0.095 Uiso 1 1 calc R U . . .
H1B H -0.0530 0.5451 0.0344 0.095 Uiso 1 1 calc R U . . .
H1C H 0.0099 0.5523 0.0938 0.095 Uiso 1 1 calc R U . . .
C3 C -0.06987(16) 0.6899(5) 0.1528(3) 0.0624(12) Uani 1 1 d . . . . .
H3A H -0.0750 0.7844 0.1839 0.094 Uiso 1 1 calc R U . . .
H3B H -0.0580 0.5918 0.1914 0.094 Uiso 1 1 calc R U . . .
H3C H -0.1034 0.6639 0.1006 0.094 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 2.001(3) 2 ?
Cu1 N1 2.001(3) . ?
Cu1 S1 2.2316(11) 2 ?
Cu1 S1 2.2317(11) . ?
S1 C4 1.750(4) . ?
C4 N2 1.300(4) . ?
C4 N3 1.369(4) . ?
C8 C9 1.360(5) . ?
C8 C7 1.370(5) . ?
C8 N4 1.467(5) . ?
C5 C10 1.389(5) . ?
C5 C6 1.401(5) . ?
C5 N3 1.403(5) . ?
C6 C7 1.377(5) . ?
C9 C10 1.387(5) . ?
C13 O3 1.221(5) . ?
C13 N5 1.319(5) . ?
C11 N5 1.438(4) . ?
C12 N5 1.448(5) . ?
N4 O1 1.218(4) . ?
N4 O2 1.223(4) . ?
N2 N1 1.408(4) . ?
N1 C2 1.297(4) . ?
C2 C3 1.481(5) . ?
C2 C1 1.491(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
N1 Cu1 N1 102.52(17) 2 . ?
N1 Cu1 S1 85.92(9) 2 2 ?
N1 Cu1 S1 147.34(9) . 2 ?
N1 Cu1 S1 147.34(9) 2 . ?
N1 Cu1 S1 85.92(9) . . ?
S1 Cu1 S1 103.98(6) 2 . ?
C4 S1 Cu1 94.09(12) . . ?
N2 C4 N3 119.3(3) . . ?
N2 C4 S1 126.4(3) . . ?
N3 C4 S1 114.3(3) . . ?
C9 C8 C7 121.3(4) . . ?
C9 C8 N4 120.3(4) . . ?
C7 C8 N4 118.4(4) . . ?
C10 C5 C6 117.8(4) . . ?
C10 C5 N3 117.9(3) . . ?
C6 C5 N3 124.3(3) . . ?
C7 C6 C5 120.8(4) . . ?
C8 C9 C10 119.4(4) . . ?
C9 C10 C5 121.1(4) . . ?
O3 C13 N5 125.5(4) . . ?
C8 C7 C6 119.6(4) . . ?
C4 N3 C5 130.4(3) . . ?
C13 N5 C11 120.9(3) . . ?
C13 N5 C12 121.8(4) . . ?
C11 N5 C12 117.3(3) . . ?
O1 N4 O2 123.9(4) . . ?
O1 N4 C8 118.7(3) . . ?
O2 N4 C8 117.4(4) . . ?
C4 N2 N1 113.0(3) . . ?
C2 N1 N2 113.7(3) . . ?
C2 N1 Cu1 128.2(2) . . ?
N2 N1 Cu1 118.0(2) . . ?
N1 C2 C3 119.2(3) . . ?
N1 C2 C1 123.1(3) . . ?
C3 C2 C1 117.7(3) . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.059

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1584981'
_audit_update_record             
;
2017-11-10 deposited with the CCDC.
2018-03-07 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         'C20 H22 N8 O4 S2 Zn, 2(C3 H7 N O)'
_chemical_formula_sum            'C26 H36 N10 O6 S2 Zn'
_chemical_formula_weight         714.16

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'
Zn Zn 0.2839 1.4301 '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        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   17.0110(7)
_cell_length_b                   7.4545(3)
_cell_length_c                   26.8950(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.247(4)
_cell_angle_gamma                90
_cell_volume                     3356.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7474
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      18.25

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.910
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.822
_exptl_absorpt_correction_T_max  0.905
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23626
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.539
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             2864
_reflns_number_gt                2344
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0800P)²+0.2500P] 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         2864
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
Zn1 Zn 0.2500 -0.08054(4) 0.0000 0.04979(18) Uani 1 2 d S T P . .
S1 S 0.33049(4) -0.22399(8) 0.06421(3) 0.0633(2) Uani 1 1 d . . . . .
O1 O 0.80451(11) 0.1997(3) 0.21158(8) 0.0789(6) Uani 1 1 d . . . . .
O2 O 0.75073(14) 0.4392(3) 0.17567(9) 0.0907(7) Uani 1 1 d . . . . .
N4 N 0.75035(13) 0.2768(3) 0.18397(8) 0.0637(6) Uani 1 1 d . . . . .
N3 N 0.47553(12) -0.1116(2) 0.10099(7) 0.0534(5) Uani 1 1 d . . . . .
H3 H 0.4735 -0.2131 0.1159 0.064 Uiso 1 1 calc R U . . .
N2 N 0.41335(11) 0.0636(2) 0.03496(7) 0.0485(5) Uani 1 1 d . . . . .
N1 N 0.34506(12) 0.0906(2) -0.00206(7) 0.0462(5) Uani 1 1 d . . . . .
C8 C 0.68073(13) 0.1741(3) 0.16023(8) 0.0521(6) Uani 1 1 d . . . . .
C7 C 0.66881(14) 0.0035(3) 0.17730(9) 0.0563(6) Uani 1 1 d . . . . .
H7 H 0.7060 -0.0485 0.2027 0.068 Uiso 1 1 calc R U . . .
C6 C 0.60120(16) -0.0880(3) 0.15618(9) 0.0543(6) Uani 1 1 d . . . . .
H6 H 0.5928 -0.2030 0.1676 0.065 Uiso 1 1 calc R U . . .
C5 C 0.54427(13) -0.0120(3) 0.11770(8) 0.0479(5) Uani 1 1 d . . . . .
C10 C 0.55947(16) 0.1595(3) 0.10058(10) 0.0669(7) Uani 1 1 d . . . . .
H10 H 0.5238 0.2120 0.0744 0.080 Uiso 1 1 calc R U . . .
C9 C 0.62712(16) 0.2506(4) 0.12244(10) 0.0688(8) Uani 1 1 d . . . . .
H9 H 0.6364 0.3655 0.1113 0.083 Uiso 1 1 calc R U . . .
C4 C 0.40994(14) -0.0733(3) 0.06421(8) 0.0463(5) Uani 1 1 d . . . . .
C3 C 0.34708(14) 0.2331(3) -0.02873(8) 0.0527(6) Uani 1 1 d . . . . .
C1 C 0.41551(19) 0.3617(4) -0.02107(11) 0.0786(9) Uani 1 1 d . . . . .
H1A H 0.4112 0.4402 0.0066 0.118 Uiso 1 1 calc R U . . .
H1B H 0.4144 0.4314 -0.0512 0.118 Uiso 1 1 calc R U . . .
H1C H 0.4648 0.2963 -0.0137 0.118 Uiso 1 1 calc R U . . .
C2 C 0.27714(16) 0.2747(4) -0.06909(9) 0.0649(7) Uani 1 1 d . . . . .
H2B H 0.2422 0.1726 -0.0743 0.097 Uiso 1 1 calc R U . . .
H2C H 0.2955 0.3024 -0.1000 0.097 Uiso 1 1 calc R U . . .
H2D H 0.2487 0.3758 -0.0590 0.097 Uiso 1 1 calc R U . . .
O3 O 0.01078(12) -0.0655(2) 0.34406(8) 0.0762(6) Uani 1 1 d . . . . .
N5 N 0.05635(12) 0.1777(2) 0.30806(7) 0.0556(5) Uani 1 1 d . . . . .
C13 C 0.06252(18) 0.0433(3) 0.34036(10) 0.0625(7) Uani 1 1 d . . . . .
H13 H 0.1110 0.0307 0.3624 0.075 Uiso 1 1 calc R U . . .
C11 C 0.12085(18) 0.3032(4) 0.30679(12) 0.0803(9) Uani 1 1 d . . . . .
H11A H 0.1678 0.2633 0.3294 0.120 Uiso 1 1 calc R U . . .
H11B H 0.1057 0.4196 0.3171 0.120 Uiso 1 1 calc R U . . .
H11C H 0.1319 0.3099 0.2731 0.120 Uiso 1 1 calc R U . . .
C12 C -0.01724(16) 0.2068(3) 0.27253(10) 0.0621(7) Uani 1 1 d . . . . .
H12A H -0.0565 0.1208 0.2786 0.093 Uiso 1 1 calc R U . . .
H12B H -0.0074 0.1931 0.2387 0.093 Uiso 1 1 calc R U . . .
H12C H -0.0366 0.3258 0.2768 0.093 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
Zn1 N1 2.0682(19) 2 ?
Zn1 N1 2.0682(19) . ?
Zn1 S1 2.2713(6) . ?
Zn1 S1 2.2714(6) 2 ?
S1 C4 1.757(2) . ?
O1 N4 1.219(3) . ?
O2 N4 1.231(3) . ?
N4 C8 1.458(3) . ?
N3 C4 1.383(3) . ?
N3 C5 1.391(3) . ?
N3 H3 0.8600 . ?
N2 C4 1.296(3) . ?
N2 N1 1.403(2) . ?
N1 C3 1.286(3) . ?
C8 C9 1.364(3) . ?
C8 C7 1.379(3) . ?
C7 C6 1.371(4) . ?
C7 H7 0.9300 . ?
C6 C5 1.405(3) . ?
C6 H6 0.9300 . ?
C5 C10 1.399(3) . ?
C10 C9 1.375(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C3 C2 1.493(3) . ?
C3 C1 1.494(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 H2D 0.9600 . ?
O3 C13 1.214(3) . ?
N5 C13 1.318(3) . ?
N5 C11 1.447(3) . ?
N5 C12 1.450(3) . ?
C13 H13 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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
N1 Zn1 N1 103.83(10) 2 . ?
N1 Zn1 S1 129.68(5) 2 . ?
N1 Zn1 S1 86.69(5) . . ?
N1 Zn1 S1 86.69(5) 2 2 ?
N1 Zn1 S1 129.68(5) . 2 ?
S1 Zn1 S1 123.83(4) . 2 ?
C4 S1 Zn1 93.37(7) . . ?
O1 N4 O2 123.1(2) . . ?
O1 N4 C8 119.1(2) . . ?
O2 N4 C8 117.8(2) . . ?
C4 N3 C5 130.25(18) . . ?
C4 N3 H3 114.9 . . ?
C5 N3 H3 114.9 . . ?
C4 N2 N1 114.99(18) . . ?
C3 N1 N2 114.41(18) . . ?
C3 N1 Zn1 128.55(16) . . ?
N2 N1 Zn1 116.43(12) . . ?
C9 C8 C7 121.0(2) . . ?
C9 C8 N4 119.4(2) . . ?
C7 C8 N4 119.6(2) . . ?
C6 C7 C8 118.9(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
N3 C5 C10 125.15(19) . . ?
N3 C5 C6 116.9(2) . . ?
C10 C5 C6 117.9(2) . . ?
C9 C10 C5 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 120.0 . . ?
C8 C9 C10 120.7(2) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
N2 C4 N3 118.6(2) . . ?
N2 C4 S1 128.37(18) . . ?
N3 C4 S1 113.00(15) . . ?
N1 C3 C2 118.7(2) . . ?
N1 C3 C1 123.4(2) . . ?
C2 C3 C1 117.9(2) . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2D 109.5 . . ?
H2B C2 H2D 109.5 . . ?
H2C C2 H2D 109.5 . . ?
C13 N5 C11 122.3(2) . . ?
C13 N5 C12 120.4(2) . . ?
C11 N5 C12 117.2(2) . . ?
O3 C13 N5 126.0(3) . . ?
O3 C13 H13 117.0 . . ?
N5 C13 H13 117.0 . . ?
N5 C11 H11A 109.5 . . ?
N5 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N5 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N5 C12 H12A 109.5 . . ?
N5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C4 N2 N1 C3 175.8(2) . . . . ?
C4 N2 N1 Zn1 4.0(2) . . . . ?
O1 N4 C8 C9 -168.0(2) . . . . ?
O2 N4 C8 C9 13.2(4) . . . . ?
O1 N4 C8 C7 13.9(3) . . . . ?
O2 N4 C8 C7 -164.9(3) . . . . ?
C9 C8 C7 C6 -1.0(4) . . . . ?
N4 C8 C7 C6 177.0(2) . . . . ?
C8 C7 C6 C5 0.1(4) . . . . ?
C4 N3 C5 C10 2.7(4) . . . . ?
C4 N3 C5 C6 -179.9(2) . . . . ?
C7 C6 C5 N3 -176.2(2) . . . . ?
C7 C6 C5 C10 1.4(4) . . . . ?
N3 C5 C10 C9 175.4(3) . . . . ?
C6 C5 C10 C9 -2.0(4) . . . . ?
C7 C8 C9 C10 0.4(4) . . . . ?
N4 C8 C9 C10 -177.6(2) . . . . ?
C5 C10 C9 C8 1.2(4) . . . . ?
N1 N2 C4 N3 178.58(18) . . . . ?
N1 N2 C4 S1 -1.7(3) . . . . ?
C5 N3 C4 N2 10.0(4) . . . . ?
C5 N3 C4 S1 -169.7(2) . . . . ?
Zn1 S1 C4 N2 -1.1(2) . . . . ?
Zn1 S1 C4 N3 178.66(16) . . . . ?
N2 N1 C3 C2 -179.76(19) . . . . ?
Zn1 N1 C3 C2 -9.1(3) . . . . ?
N2 N1 C3 C1 -0.7(4) . . . . ?
Zn1 N1 C3 C1 170.0(2) . . . . ?
C11 N5 C13 O3 179.0(3) . . . . ?
C12 N5 C13 O3 0.1(4) . . . . ?

_refine_diff_density_max         0.247
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_H2Lmethoxy
_database_code_depnum_ccdc_archive 'CCDC 1572109'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-07 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         'C11 H15 N3 O S'
_chemical_formula_sum            'C11 H15 N3 O S'
_chemical_formula_weight         237.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.3214(13)
_cell_length_b                   11.3148(16)
_cell_length_c                   12.7860(16)
_cell_angle_alpha                78.642(9)
_cell_angle_beta                 69.657(9)
_cell_angle_gamma                75.860(9)
_cell_volume                     1216.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3988
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.11

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.250
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   none
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16473
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.712
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.050
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             4214
_reflns_number_gt                3169
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0500P)²+0.5000P] 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         4214
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1243
_refine_ls_wR_factor_gt          0.1084
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
S1 S 0.66250(8) 0.16754(6) 1.13002(5) 0.0565(2) Uani 1 1 d . . . . .
S2 S 0.36370(8) 0.90588(6) 0.28678(6) 0.0605(2) Uani 1 1 d . . . . .
C14 C 0.2254(3) 0.1375(2) 1.00860(19) 0.0469(6) Uani 1 1 d . . . . .
C15 C 0.5539(3) 0.2025(2) 1.04304(19) 0.0455(5) Uani 1 1 d . . . . .
C8 C 0.5088(3) 0.8463(2) 0.34141(19) 0.0470(6) Uani 1 1 d . . . . .
C9 C 0.8048(3) 0.9362(2) 0.39763(19) 0.0493(6) Uani 1 1 d . . . . .
C16 C 0.7099(3) 0.3468(2) 0.90636(19) 0.0467(6) Uani 1 1 d . . . . .
C19 C 0.9463(3) 0.4790(2) 0.8157(2) 0.0501(6) Uani 1 1 d . . . . .
C5 C 0.4577(3) 0.6369(2) 0.3869(2) 0.0497(6) Uani 1 1 d . . . . .
C2 C 0.3020(3) 0.4549(2) 0.39407(19) 0.0480(6) Uani 1 1 d . . . . .
C21 C 0.8208(3) 0.3233(2) 0.8055(2) 0.0506(6) Uani 1 1 d . . . . .
H21 H 0.8159 0.2630 0.7675 0.061 Uiso 1 1 calc R U . . .
C17 C 0.7158(3) 0.4373(2) 0.9606(2) 0.0576(6) Uani 1 1 d . . . . .
H17 H 0.6392 0.4543 1.0283 0.069 Uiso 1 1 calc R U . . .
C20 C 0.9388(3) 0.3885(2) 0.7607(2) 0.0536(6) Uani 1 1 d . . . . .
H20 H 1.0146 0.3715 0.6926 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8349(3) 0.5042(2) 0.9159(2) 0.0574(7) Uani 1 1 d . . . . .
H18 H 0.8389 0.5653 0.9535 0.069 Uiso 1 1 calc R U . . .
C6 C 0.3117(3) 0.6328(2) 0.4632(2) 0.0569(6) Uani 1 1 d . . . . .
H6 H 0.2652 0.6915 0.5128 0.068 Uiso 1 1 calc R U . . .
C7 C 0.2341(3) 0.5422(2) 0.4664(2) 0.0556(6) Uani 1 1 d . . . . .
H7 H 0.1353 0.5404 0.5179 0.067 Uiso 1 1 calc R U . . .
C3 C 0.4485(3) 0.4564(2) 0.3192(2) 0.0572(6) Uani 1 1 d . . . . .
H3 H 0.4960 0.3963 0.2711 0.069 Uiso 1 1 calc R U . . .
C4 C 0.5255(3) 0.5487(2) 0.3156(2) 0.0599(7) Uani 1 1 d . . . . .
H4 H 0.6243 0.5506 0.2641 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1397(3) 0.1779(3) 0.9247(2) 0.0661(7) Uani 1 1 d . . . . .
H13A H 0.1871 0.2388 0.8682 0.099 Uiso 1 1 calc R U . . .
H13B H 0.0330 0.2124 0.9617 0.099 Uiso 1 1 calc R U . . .
H13C H 0.1438 0.1087 0.8900 0.099 Uiso 1 1 calc R U . . .
C12 C 0.1641(3) 0.0462(3) 1.1053(2) 0.0646(7) Uani 1 1 d . . . . .
H12A H 0.2303 -0.0330 1.0947 0.097 Uiso 1 1 calc R U . . .
H12B H 0.0604 0.0419 1.1100 0.097 Uiso 1 1 calc R U . . .
H12C H 0.1621 0.0709 1.1735 0.097 Uiso 1 1 calc R U . . .
C10 C 0.9431(3) 0.8774(3) 0.4348(3) 0.0714(8) Uani 1 1 d . . . . .
H10A H 0.9535 0.7897 0.4442 0.107 Uiso 1 1 calc R U . . .
H10B H 0.9299 0.9038 0.5050 0.107 Uiso 1 1 calc R U . . .
H10C H 1.0350 0.9006 0.3793 0.107 Uiso 1 1 calc R U . . .
C11 C 0.7664(4) 1.0729(3) 0.3829(3) 0.0708(8) Uani 1 1 d . . . . .
H11A H 0.8089 1.1031 0.3051 0.106 Uiso 1 1 calc R U . . .
H11B H 0.8104 1.1040 0.4272 0.106 Uiso 1 1 calc R U . . .
H11C H 0.6553 1.0998 0.4069 0.106 Uiso 1 1 calc R U . . .
C1 C 0.2769(4) 0.2822(3) 0.3262(3) 0.0786(9) Uani 1 1 d . . . . .
H1A H 0.3061 0.3229 0.2507 0.118 Uiso 1 1 calc R U . . .
H1B H 0.2002 0.2345 0.3352 0.118 Uiso 1 1 calc R U . . .
H1C H 0.3671 0.2290 0.3409 0.118 Uiso 1 1 calc R U . . .
C22 C 1.0764(4) 0.6389(3) 0.8097(3) 0.0826(9) Uani 1 1 d . . . . .
H22A H 0.9851 0.7010 0.8113 0.124 Uiso 1 1 calc R U . . .
H22B H 1.1676 0.6716 0.7644 0.124 Uiso 1 1 calc R U . . .
H22C H 1.0810 0.6128 0.8848 0.124 Uiso 1 1 calc R U . . .
O1 O 0.2140(2) 0.37058(16) 0.40242(15) 0.0644(5) Uani 1 1 d . . . . .
O2 O 1.0702(2) 0.53798(17) 0.76355(16) 0.0689(5) Uani 1 1 d . . . . .
N2 N 0.6005(2) 0.9193(2) 0.34665(18) 0.0510(5) Uani 1 1 d . . . . .
N5 N 0.4293(2) 0.15133(19) 1.06466(17) 0.0491(5) Uani 1 1 d . . . . .
N4 N 0.3440(2) 0.18502(18) 0.99057(16) 0.0498(5) Uani 1 1 d . . . . .
N6 N 0.5843(3) 0.2812(2) 0.94892(18) 0.0551(6) Uani 1 1 d . . . . .
N1 N 0.5400(3) 0.72929(19) 0.38425(19) 0.0576(6) Uani 1 1 d . . . . .
N3 N 0.7284(2) 0.86533(18) 0.38234(17) 0.0524(5) Uani 1 1 d . . . . .
H2 H 0.596(3) 0.992(2) 0.3085(19) 0.049(7) Uiso 1 1 d . . . . .
H1 H 0.622(3) 0.709(3) 0.403(2) 0.070(9) Uiso 1 1 d . . . . .
H6A H 0.530(3) 0.280(2) 0.911(2) 0.056(8) Uiso 1 1 d . . . . .
H5 H 0.413(3) 0.097(2) 1.118(2) 0.052(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C15 1.683(2) . ?
S2 C8 1.672(2) . ?
C14 N4 1.277(3) . ?
C14 C12 1.488(3) . ?
C14 C13 1.491(3) . ?
C15 N6 1.336(3) . ?
C15 N5 1.343(3) . ?
C8 N1 1.333(3) . ?
C8 N2 1.350(3) . ?
C9 N3 1.275(3) . ?
C9 C10 1.488(4) . ?
C9 C11 1.489(4) . ?
C16 C17 1.366(3) . ?
C16 C21 1.369(3) . ?
C16 N6 1.429(3) . ?
C19 C18 1.369(4) . ?
C19 O2 1.374(3) . ?
C19 C20 1.379(3) . ?
C5 C4 1.370(4) . ?
C5 C6 1.377(4) . ?
C5 N1 1.429(3) . ?
C2 O1 1.369(3) . ?
C2 C3 1.370(4) . ?
C2 C7 1.372(4) . ?
C21 C20 1.369(3) . ?
C17 C18 1.390(4) . ?
C6 C7 1.378(4) . ?
C3 C4 1.390(4) . ?
C1 O1 1.412(3) . ?
C22 O2 1.406(3) . ?
N2 N3 1.384(3) . ?
N5 N4 1.381(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
N4 C14 C12 126.4(2) . . ?
N4 C14 C13 116.7(2) . . ?
C12 C14 C13 116.9(2) . . ?
N6 C15 N5 115.4(2) . . ?
N6 C15 S1 123.34(19) . . ?
N5 C15 S1 121.21(17) . . ?
N1 C8 N2 115.8(2) . . ?
N1 C8 S2 124.33(19) . . ?
N2 C8 S2 119.82(18) . . ?
N3 C9 C10 117.2(2) . . ?
N3 C9 C11 125.7(2) . . ?
C10 C9 C11 117.1(2) . . ?
C17 C16 C21 119.7(2) . . ?
C17 C16 N6 121.3(2) . . ?
C21 C16 N6 118.9(2) . . ?
C18 C19 O2 124.5(2) . . ?
C18 C19 C20 119.9(2) . . ?
O2 C19 C20 115.6(2) . . ?
C4 C5 C6 119.0(2) . . ?
C4 C5 N1 120.2(2) . . ?
C6 C5 N1 120.7(2) . . ?
O1 C2 C3 124.3(2) . . ?
O1 C2 C7 115.7(2) . . ?
C3 C2 C7 120.0(2) . . ?
C16 C21 C20 120.0(2) . . ?
C16 C17 C18 120.8(2) . . ?
C21 C20 C19 120.5(2) . . ?
C19 C18 C17 119.0(2) . . ?
C5 C6 C7 120.4(2) . . ?
C2 C7 C6 120.3(2) . . ?
C2 C3 C4 119.4(2) . . ?
C5 C4 C3 120.9(3) . . ?
C2 O1 C1 117.6(2) . . ?
C19 O2 C22 118.4(2) . . ?
C8 N2 N3 118.4(2) . . ?
C15 N5 N4 118.31(19) . . ?
C14 N4 N5 119.73(19) . . ?
C15 N6 C16 126.6(2) . . ?
C8 N1 C5 124.9(2) . . ?
C9 N3 N2 117.6(2) . . ?

_refine_diff_density_max         0.236
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_Lmethoxy
_database_code_depnum_ccdc_archive 'CCDC 1572111'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-07 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         'C11 H13 N3 O S'
_chemical_formula_sum            'C11 H13 N3 O S'
_chemical_formula_weight         235.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   5.9381(5)
_cell_length_b                   6.2676(6)
_cell_length_c                   17.4543(17)
_cell_angle_alpha                99.804(8)
_cell_angle_beta                 91.409(7)
_cell_angle_gamma                109.424(8)
_cell_volume                     601.38(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1378
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      24.15

_exptl_crystal_description       Needle
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.252
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   multi-scan
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3612
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.486
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.049
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2129
_reflns_number_gt                1577
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0800P)²+0.0100P] 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         2129
_refine_ls_number_parameters     148
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0655
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.27539(13) -0.45581(11) 0.24810(4) 0.0635(3) Uani 1 1 d . . . . .
O1 O 0.3194(3) 0.2130(3) 0.02549(10) 0.0621(5) Uani 1 1 d . . . . .
N1 N 0.1237(3) -0.0922(3) 0.30508(11) 0.0438(5) Uani 1 1 d . . . . .
N3 N -0.0454(4) -0.2997(4) 0.39426(14) 0.0606(6) Uani 1 1 d . . . . .
N2 N 0.1306(4) -0.1396(4) 0.43091(13) 0.0617(6) Uani 1 1 d . . . . .
C7 C -0.0610(4) -0.2783(4) 0.31213(14) 0.0478(6) Uani 1 1 d . . . . .
C1 C 0.1755(4) -0.0073(4) 0.23407(13) 0.0413(6) Uani 1 1 d . . . . .
C4 C 0.2667(4) 0.1502(4) 0.09556(13) 0.0435(6) Uani 1 1 d . . . . .
C3 C 0.3833(4) 0.0103(4) 0.11895(14) 0.0473(6) Uani 1 1 d . . . . .
H3 H 0.4940 -0.0294 0.0881 0.057 Uiso 1 1 calc R U . . .
C5 C 0.1071(5) 0.2139(4) 0.14292(15) 0.0516(7) Uani 1 1 d . . . . .
H5 H 0.0307 0.3103 0.1283 0.062 Uiso 1 1 calc R U . . .
C6 C 0.0620(4) 0.1338(4) 0.21176(15) 0.0504(7) Uani 1 1 d . . . . .
H6 H -0.0460 0.1756 0.2434 0.060 Uiso 1 1 calc R U . . .
C8 C 0.2619(4) 0.0169(4) 0.38024(14) 0.0511(7) Uani 1 1 d . . . . .
C2 C 0.3365(4) -0.0696(4) 0.18706(14) 0.0459(6) Uani 1 1 d . . . . .
H2 H 0.4128 -0.1658 0.2018 0.055 Uiso 1 1 calc R U . . .
C9 C 0.2498(5) 0.2557(5) 0.40915(16) 0.0705(9) Uani 1 1 d . . . . .
H9A H 0.3338 0.3583 0.3761 0.106 Uiso 1 1 calc R U . . .
H9B H 0.3226 0.3122 0.4617 0.106 Uiso 1 1 calc R U . . .
H9C H 0.0852 0.2472 0.4079 0.106 Uiso 1 1 calc R U . . .
C10 C 0.5173(5) 0.0180(6) 0.37997(16) 0.0719(9) Uani 1 1 d . . . . .
H10A H 0.5162 -0.1372 0.3659 0.108 Uiso 1 1 calc R U . . .
H10B H 0.5988 0.0856 0.4310 0.108 Uiso 1 1 calc R U . . .
H10C H 0.5986 0.1064 0.3428 0.108 Uiso 1 1 calc R U . . .
C11 C 0.1967(6) 0.3498(5) -0.00218(18) 0.0689(8) Uani 1 1 d . . . . .
H11A H 0.0268 0.2738 -0.0031 0.103 Uiso 1 1 calc R U . . .
H11B H 0.2379 0.3701 -0.0539 0.103 Uiso 1 1 calc R U . . .
H11C H 0.2428 0.4976 0.0319 0.103 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
S1 C7 1.635(3) . ?
O1 C4 1.360(3) . ?
O1 C11 1.428(3) . ?
N1 C7 1.335(3) . ?
N1 C1 1.431(3) . ?
N1 C8 1.460(3) . ?
N3 N2 1.249(3) . ?
N3 C7 1.466(3) . ?
N2 C8 1.474(3) . ?
C1 C6 1.375(3) . ?
C1 C2 1.384(3) . ?
C4 C5 1.385(3) . ?
C4 C3 1.388(3) . ?
C3 C2 1.367(3) . ?
C5 C6 1.378(3) . ?
C8 C10 1.514(4) . ?
C8 C9 1.522(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
C4 O1 C11 117.6(2) . . ?
C7 N1 C1 124.7(2) . . ?
C7 N1 C8 110.72(19) . . ?
C1 N1 C8 124.53(18) . . ?
N2 N3 C7 110.0(2) . . ?
N3 N2 C8 111.9(2) . . ?
N1 C7 N3 106.1(2) . . ?
N1 C7 S1 131.0(2) . . ?
N3 C7 S1 122.85(18) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 N1 119.9(2) . . ?
C2 C1 N1 120.4(2) . . ?
O1 C4 C5 124.8(2) . . ?
O1 C4 C3 115.7(2) . . ?
C5 C4 C3 119.5(2) . . ?
C2 C3 C4 120.4(2) . . ?
C6 C5 C4 119.7(2) . . ?
C1 C6 C5 120.5(2) . . ?
N1 C8 N2 101.21(19) . . ?
N1 C8 C10 112.5(2) . . ?
N2 C8 C10 109.1(2) . . ?
N1 C8 C9 112.0(2) . . ?
N2 C8 C9 109.0(2) . . ?
C10 C8 C9 112.3(2) . . ?
C3 C2 C1 120.0(2) . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.038

