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

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

data_il
_database_code_depnum_ccdc_archive 'CCDC 1052678'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2013-12-03
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C10 H10 N4 O S, H2 O'
_chemical_formula_sum            'C10 H12 N4 O2 S'
_chemical_formula_weight         252.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.830(2)
_cell_length_b                   12.980(3)
_cell_length_c                   10.115(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.870(3)
_cell_angle_gamma                90
_cell_volume                     1156.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6880
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.488
_cell_measurement_theta_min      2.312
_shelx_estimated_absorpt_T_max   0.934
_shelx_estimated_absorpt_T_min   0.902
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0564 before and 0.0378 after correction.
The Ratio of minimum to maximum transmission is 0.9382.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13112
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.522
_diffrn_reflns_theta_min         2.312
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2449
_reflns_number_total             2656
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         2656
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0349P)²+0.7452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0808
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Riding coordinates:
 O1W(H1WA,H1WB)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), N4(H4), C1(H1A), C2(H2), C3(H3A), C4(H4A)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.00285(4) 0.62176(2) 0.26732(3) 0.01794(10) Uani 1 1 d . . . . .
O1 O 0.30059(11) 0.88929(7) 0.16153(9) 0.0203(2) Uani 1 1 d . . . . .
N1 N 0.40945(12) 1.03554(9) 0.25810(11) 0.0175(2) Uani 1 1 d . . . . .
H1 H 0.4677 1.0539 0.1949 0.021 Uiso 1 1 calc R U . . .
N2 N 0.14710(12) 0.88221(8) 0.41948(11) 0.0150(2) Uani 1 1 d . . . . .
N3 N 0.11616(12) 0.80239(8) 0.33544(11) 0.0165(2) Uani 1 1 d . . . . .
H3 H 0.1498 0.8033 0.2555 0.020 Uiso 1 1 calc R U . . .
N4 N -0.01796(12) 0.72505(8) 0.49403(11) 0.0164(2) Uani 1 1 d . . . . .
H4 H 0.0058 0.7791 0.5436 0.020 Uiso 1 1 calc R U . . .
C1 C 0.48199(15) 1.17396(10) 0.42343(14) 0.0202(3) Uani 1 1 d . . . . .
H1A H 0.5534 1.2063 0.3708 0.024 Uiso 1 1 calc R U . . .
C2 C 0.45454(16) 1.21071(11) 0.54939(14) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.5090 1.2691 0.5834 0.027 Uiso 1 1 calc R U . . .
C3 C 0.34940(16) 1.16387(11) 0.62624(14) 0.0227(3) Uani 1 1 d . . . . .
H3A H 0.3329 1.1909 0.7113 0.027 Uiso 1 1 calc R U . . .
C4 C 0.26802(15) 1.07775(10) 0.57993(13) 0.0185(3) Uani 1 1 d . . . . .
H4A H 0.1962 1.0456 0.6323 0.022 Uiso 1 1 calc R U . . .
C5 C 0.29475(14) 1.04034(10) 0.45541(12) 0.0149(2) Uani 1 1 d . . . . .
C6 C 0.40083(14) 1.08859(10) 0.37894(13) 0.0160(3) Uani 1 1 d . . . . .
C7 C 0.23821(14) 0.95158(10) 0.38002(12) 0.0143(2) Uani 1 1 d . . . . .
C8 C 0.31689(14) 0.95307(10) 0.25224(13) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.03268(14) 0.72044(10) 0.37491(12) 0.0145(2) Uani 1 1 d . . . . .
C10 C -0.11136(17) 0.64497(11) 0.54778(14) 0.0224(3) Uani 1 1 d . . . . .
H10A H -0.1966 0.6291 0.4839 0.034 Uiso 1 1 calc R U . . .
H10B H -0.1504 0.6690 0.6308 0.034 Uiso 1 1 calc R U . . .
H10C H -0.0501 0.5828 0.5648 0.034 Uiso 1 1 calc R U . . .
O1W O 0.34702(11) 0.55862(8) 0.39906(10) 0.0252(2) Uani 1 1 d . . . . .
H1WA H 0.2551 0.5667 0.3704 0.038 Uiso 1 1 d R U . . .
H1WB H 0.3528 0.5587 0.4833 0.038 Uiso 1 1 d 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 C9 1.6900(13) . ?
O1 C8 1.2370(16) . ?
N1 H1 0.8800 . ?
N1 C6 1.4094(17) . ?
N1 C8 1.3457(17) . ?
N2 N3 1.3562(15) . ?
N2 C7 1.2886(17) . ?
N3 H3 0.8800 . ?
N3 C9 1.3689(16) . ?
N4 H4 0.8800 . ?
N4 C9 1.3146(17) . ?
N4 C10 1.4549(17) . ?
C1 H1A 0.9500 . ?
C1 C2 1.397(2) . ?
C1 C6 1.3785(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.390(2) . ?
C3 H3A 0.9500 . ?
C3 C4 1.3928(19) . ?
C4 H4A 0.9500 . ?
C4 C5 1.3849(18) . ?
C5 C6 1.4021(18) . ?
C5 C7 1.4515(18) . ?
C7 C8 1.5082(17) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O1W H1WA 0.8499 . ?
O1W H1WB 0.8500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 H1 124.5 . . ?
C8 N1 H1 124.5 . . ?
C8 N1 C6 111.02(11) . . ?
C7 N2 N3 116.31(11) . . ?
N2 N3 H3 120.0 . . ?
N2 N3 C9 120.03(10) . . ?
C9 N3 H3 120.0 . . ?
C9 N4 H4 118.4 . . ?
C9 N4 C10 123.12(11) . . ?
C10 N4 H4 118.4 . . ?
C2 C1 H1A 121.5 . . ?
C6 C1 H1A 121.5 . . ?
C6 C1 C2 117.00(13) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 C1 121.60(13) . . ?
C3 C2 H2 119.2 . . ?
C2 C3 H3A 119.6 . . ?
C2 C3 C4 120.78(13) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 H4A 120.9 . . ?
C5 C4 C3 118.14(12) . . ?
C5 C4 H4A 120.9 . . ?
C4 C5 C6 120.42(12) . . ?
C4 C5 C7 133.03(12) . . ?
C6 C5 C7 106.48(11) . . ?
C1 C6 N1 128.21(12) . . ?
C1 C6 C5 122.06(13) . . ?
C5 C6 N1 109.71(11) . . ?
N2 C7 C5 126.28(12) . . ?
N2 C7 C8 127.42(12) . . ?
C5 C7 C8 106.14(11) . . ?
O1 C8 N1 127.23(12) . . ?
O1 C8 C7 126.14(12) . . ?
N1 C8 C7 106.62(11) . . ?
N3 C9 S1 117.69(9) . . ?
N4 C9 S1 125.23(10) . . ?
N4 C9 N3 117.08(11) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
H1WA O1W H1WB 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1W 0.88 1.95 2.7754(15) 156.1 2_655
N3 H3 O1 0.88 2.02 2.7213(15) 135.4 .
N4 H4 S1 0.88 2.60 3.4001(13) 150.9 4_576
O1W H1WA S1 0.85 2.50 3.3371(13) 169.0 .
O1W H1WB O1 0.85 2.01 2.7965(15) 154.0 4_576

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
N2 N3 C9 S1 -178.09(9) . . . . ?
N2 N3 C9 N4 1.92(17) . . . . ?
N2 C7 C8 O1 3.5(2) . . . . ?
N2 C7 C8 N1 -175.26(12) . . . . ?
N3 N2 C7 C5 -176.16(11) . . . . ?
N3 N2 C7 C8 -1.35(19) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C1 C6 N1 -178.53(12) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.12(19) . . . . ?
C3 C4 C5 C7 176.41(13) . . . . ?
C4 C5 C6 N1 179.00(11) . . . . ?
C4 C5 C6 C1 0.02(19) . . . . ?
C4 C5 C7 N2 -2.4(2) . . . . ?
C4 C5 C7 C8 -178.11(13) . . . . ?
C5 C7 C8 O1 179.16(12) . . . . ?
C5 C7 C8 N1 0.39(13) . . . . ?
C6 N1 C8 O1 -178.13(13) . . . . ?
C6 N1 C8 C7 0.63(14) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C5 C7 N2 174.47(12) . . . . ?
C6 C5 C7 C8 -1.23(13) . . . . ?
C7 N2 N3 C9 173.56(11) . . . . ?
C7 C5 C6 N1 1.65(14) . . . . ?
C7 C5 C6 C1 -177.33(12) . . . . ?
C8 N1 C6 C1 177.42(13) . . . . ?
C8 N1 C6 C5 -1.47(14) . . . . ?
C10 N4 C9 S1 -1.65(18) . . . . ?
C10 N4 C9 N3 178.35(12) . . . . ?

####################################################################### 
# 
# 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_aism
_database_code_depnum_ccdc_archive 'CCDC 1052679'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2014-04-15
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H14 N4 O S'
_chemical_formula_sum            'C13 H14 N4 O S'
_chemical_formula_weight         274.34
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.845(4)
_cell_length_b                   15.614(11)
_cell_length_c                   24.566(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2626(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4859
_cell_measurement_temperature    150.15
_cell_measurement_theta_max      27.308
_cell_measurement_theta_min      2.609
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4734
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.0977 before and 0.0723 after correction.
The Ratio of minimum to maximum transmission is 0.6349.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.388
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0899
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            19472
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.687
_diffrn_reflns_theta_min         1.658
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2467
_reflns_number_total             3019
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3019
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0659
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1274P)²+1.8169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1853
_refine_ls_wR_factor_ref         0.1983
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 C13(H13A,H13B)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C1(H1), C2(H2), C3(H3A), C4(H4A), C12(H12)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.48631(9) 0.89254(4) 0.45804(2) 0.0261(2) Uani 1 1 d . . . . .
O1 O 0.6041(3) 0.95657(10) 0.28078(6) 0.0249(4) Uani 1 1 d . . . . .
N1 N 0.5946(3) 0.89115(11) 0.19611(7) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.5330(3) 0.77476(12) 0.31936(8) 0.0189(4) Uani 1 1 d . . . . .
N3 N 0.5435(3) 0.83473(13) 0.35912(7) 0.0204(4) Uani 1 1 d . . . . .
H3 H 0.5710 0.8881 0.3506 0.025 Uiso 1 1 calc R U . . .
N4 N 0.4992(3) 0.72958(13) 0.42288(8) 0.0231(5) Uani 1 1 d . . . . .
H4 H 0.5191 0.6941 0.3956 0.028 Uiso 1 1 calc R U . . .
C1 C 0.5473(4) 0.78028(15) 0.12274(9) 0.0215(5) Uani 1 1 d . . . . .
H1 H 0.5608 0.8194 0.0933 0.026 Uiso 1 1 calc R U . . .
C2 C 0.5144(3) 0.69304(16) 0.11376(10) 0.0230(5) Uani 1 1 d . . . . .
H2 H 0.5061 0.6723 0.0775 0.028 Uiso 1 1 calc R U . . .
C3 C 0.4936(3) 0.63578(16) 0.15688(10) 0.0222(5) Uani 1 1 d . . . . .
H3A H 0.4722 0.5768 0.1495 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5035(3) 0.66377(15) 0.21093(9) 0.0208(5) Uani 1 1 d . . . . .
H4A H 0.4882 0.6248 0.2403 0.025 Uiso 1 1 calc R U . . .
C5 C 0.5365(3) 0.75030(15) 0.22031(9) 0.0175(5) Uani 1 1 d . . . . .
C6 C 0.5594(3) 0.80731(14) 0.17638(9) 0.0172(5) Uani 1 1 d . . . . .
C7 C 0.5513(3) 0.80192(14) 0.26979(8) 0.0176(5) Uani 1 1 d . . . . .
C8 C 0.5859(3) 0.89255(13) 0.25150(9) 0.0187(5) Uani 1 1 d . . . . .
C9 C 0.5112(3) 0.81288(16) 0.41305(9) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.4551(4) 0.69330(17) 0.47594(10) 0.0294(6) Uani 1 1 d . . . . .
H10A H 0.3656 0.6448 0.4716 0.044 Uiso 1 1 calc R U . . .
H10B H 0.3937 0.7370 0.4989 0.044 Uiso 1 1 calc R U . . .
H10C H 0.5762 0.6736 0.4931 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6366(3) 0.96668(14) 0.16239(9) 0.0208(5) Uani 1 1 d . . . . .
H11A H 0.7267 0.9499 0.1327 0.025 Uiso 1 1 calc R U . . .
H11B H 0.7038 1.0101 0.1850 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4588(4) 1.00570(16) 0.13819(11) 0.0285(6) Uani 1 1 d . . . . .
H12 H 0.3635 1.0292 0.1620 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4267(5) 1.00933(18) 0.08537(12) 0.0420(7) Uani 1 1 d . . . . .
H13A H 0.5137 0.9875 0.0586 0.050 Uiso 1 1 d R U . . .
H13B H 0.3151 1.0390 0.0722 0.050 Uiso 1 1 d 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 C9 1.673(3) . ?
O1 C8 1.238(3) . ?
N1 C6 1.417(3) . ?
N1 C8 1.362(3) . ?
N1 C11 1.470(3) . ?
N2 N3 1.355(3) . ?
N2 C7 1.296(3) . ?
N3 H3 0.8800 . ?
N3 C9 1.386(3) . ?
N4 H4 0.8800 . ?
N4 C9 1.325(3) . ?
N4 C10 1.453(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.398(4) . ?
C1 C6 1.386(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.393(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.400(3) . ?
C4 H4A 0.9500 . ?
C4 C5 1.389(3) . ?
C5 C6 1.408(3) . ?
C5 C7 1.462(3) . ?
C7 C8 1.504(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.485(3) . ?
C12 H12 0.9500 . ?
C12 C13 1.317(4) . ?
C13 H13A 0.9498 . ?
C13 H13B 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C11 125.59(18) . . ?
C8 N1 C6 110.44(17) . . ?
C8 N1 C11 123.97(17) . . ?
C7 N2 N3 116.5(2) . . ?
N2 N3 H3 119.7 . . ?
N2 N3 C9 120.7(2) . . ?
C9 N3 H3 119.7 . . ?
C9 N4 H4 118.0 . . ?
C9 N4 C10 124.0(2) . . ?
C10 N4 H4 118.0 . . ?
C2 C1 H1 121.4 . . ?
C6 C1 H1 121.4 . . ?
C6 C1 C2 117.1(2) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.4(2) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3A 119.5 . . ?
C2 C3 C4 121.1(2) . . ?
C4 C3 H3A 119.5 . . ?
C3 C4 H4A 121.0 . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 H4A 121.0 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 C7 133.3(2) . . ?
C6 C5 C7 106.3(2) . . ?
C1 C6 N1 128.1(2) . . ?
C1 C6 C5 122.0(2) . . ?
C5 C6 N1 109.9(2) . . ?
N2 C7 C5 126.5(2) . . ?
N2 C7 C8 127.2(2) . . ?
C5 C7 C8 106.35(18) . . ?
O1 C8 N1 126.1(2) . . ?
O1 C8 C7 127.0(2) . . ?
N1 C8 C7 106.87(17) . . ?
N3 C9 S1 117.70(18) . . ?
N4 C9 S1 127.08(18) . . ?
N4 C9 N3 115.2(2) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
N1 C11 C12 113.26(19) . . ?
H11A C11 H11B 107.7 . . ?
C12 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C11 C12 H12 118.4 . . ?
C13 C12 C11 123.3(3) . . ?
C13 C12 H12 118.4 . . ?
C12 C13 H13A 124.1 . . ?
C12 C13 H13B 119.4 . . ?
H13A C13 H13B 116.3 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.88 2.03 2.738(3) 136.2 .

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C11 C12 C13 -116.3(3) . . . . ?
N2 N3 C9 S1 -169.07(16) . . . . ?
N2 N3 C9 N4 9.5(3) . . . . ?
N2 C7 C8 O1 0.5(4) . . . . ?
N2 C7 C8 N1 -179.8(2) . . . . ?
N3 N2 C7 C5 -177.1(2) . . . . ?
N3 N2 C7 C8 1.0(3) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C1 C6 N1 178.9(2) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C2 C3 C4 C5 -0.5(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C3 C4 C5 C7 178.4(2) . . . . ?
C4 C5 C6 N1 -179.0(2) . . . . ?
C4 C5 C6 C1 1.0(3) . . . . ?
C4 C5 C7 N2 -0.8(4) . . . . ?
C4 C5 C7 C8 -179.2(2) . . . . ?
C5 C7 C8 O1 178.9(2) . . . . ?
C5 C7 C8 N1 -1.4(2) . . . . ?
C6 N1 C8 O1 -177.6(2) . . . . ?
C6 N1 C8 C7 2.7(2) . . . . ?
C6 N1 C11 C12 80.2(3) . . . . ?
C6 C1 C2 C3 0.3(3) . . . . ?
C6 C5 C7 N2 178.0(2) . . . . ?
C6 C5 C7 C8 -0.4(2) . . . . ?
C7 N2 N3 C9 175.2(2) . . . . ?
C7 C5 C6 N1 2.1(3) . . . . ?
C7 C5 C6 C1 -178.0(2) . . . . ?
C8 N1 C6 C1 176.9(2) . . . . ?
C8 N1 C6 C5 -3.1(3) . . . . ?
C8 N1 C11 C12 -100.3(3) . . . . ?
C10 N4 C9 S1 2.0(3) . . . . ?
C10 N4 C9 N3 -176.4(2) . . . . ?
C11 N1 C6 C1 -3.6(4) . . . . ?
C11 N1 C6 C5 176.4(2) . . . . ?
C11 N1 C8 O1 2.9(4) . . . . ?
C11 N1 C8 C7 -176.8(2) . . . . ?

####################################################################### 
# 
# 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_niip
_database_code_depnum_ccdc_archive 'CCDC 1052682'
_audit_update_record             
;
2015-03-07 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_audit_creation_date             2014-01-09
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H18 N8 Ni O2 S2, 3(C3 H7 N1 O1)'
_chemical_formula_sum            'C29 H39 N11 Ni O5 S2'
_chemical_formula_weight         744.54
_chemical_melting_point          ?
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'
Ni Ni 0.3393 1.1124 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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                   19.2985(14)
_cell_length_b                   11.9741(14)
_cell_length_c                   15.3857(13)
_cell_angle_alpha                90
_cell_angle_beta                 106.181(4)
_cell_angle_gamma                90
_cell_volume                     3414.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9615
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      38.50
_cell_measurement_theta_min      3.01
_shelx_estimated_absorpt_T_max   0.725
_shelx_estimated_absorpt_T_min   0.680
_exptl_absorpt_coefficient_mu    0.746
_exptl_absorpt_correction_T_max  0.6356
_exptl_absorpt_correction_T_min  0.5450
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2012/1 (Bruker,2012) was used for absorption correction.
wR2(int) was 0.1134 before and 0.0967 after correction.
The Ratio of minimum to maximum transmission is 0.8575.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1560
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.54
_exptl_crystal_size_min          0.46
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            94121
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         38.714
_diffrn_reflns_theta_min         2.025
_diffrn_ambient_temperature      110(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                8419
_reflns_number_total             9435
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    ?
_refine_diff_density_max         0.591
_refine_diff_density_min         -0.797
_refine_diff_density_rms         0.074
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         9435
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0346
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+2.4776P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0965
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N22-C24 \\sim N22-C23
 with sigma of 0.02
 N17-C20 \\sim N17A-C20A \\sim N17-C19 \\sim N17A-C19A
 with sigma of 0.02
 N17-C18 \\sim N17A-C18A
 with sigma of 0.02
 O16-C18 \\sim O16A-C18A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C24) = Uanis(C21)
Uanis(O16) = Uanis(O16A)
Uanis(N17) = Uanis(N17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C20) = Uanis(C20A)
4. Same fragment restrains
{O16, N17, C18, C19, C20}
as
{O16A, N17A, C18A, C19A, C20A}
5. Others
 Sof(O16A)=Sof(N17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19D)=Sof(H19E)=
 Sof(H19F)=Sof(C20A)=Sof(H20D)=Sof(H20E)=Sof(H20F)=1-FVAR(1)
 Sof(O16)=Sof(N17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(H19C)=
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(H20C)=FVAR(1)
 Fixed Sof: O20(0.5) C21(0.5) H21(0.5) N22(0.5) C23(0.5) H23A(0.5) H23B(0.5)
 H23C(0.5) C24(0.5) H24A(0.5) H24B(0.5) H24C(0.5)
6.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C18(H18), C18A(H18A), C21(H21)
6.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C), C19A(H19D,H19E,
 H19F), C20A(H20D,H20E,H20F), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.01083(2) 0.7500 0.01296(4) Uani 1 2 d S T P . .
S1 S -0.04308(2) -0.12007(2) 0.63199(2) 0.01580(4) Uani 1 1 d . . . . .
O1 O 0.06516(4) 0.14289(5) 0.83560(5) 0.02204(12) Uani 1 1 d . . . . .
N1 N 0.17811(5) 0.21820(7) 0.84177(5) 0.02265(14) Uani 1 1 d . . . . .
H1 H 0.1835 0.2642 0.8878 0.027 Uiso 1 1 calc R U . . .
N2 N 0.08110(4) 0.02106(5) 0.69138(4) 0.01208(9) Uani 1 1 d . . . . .
N3 N 0.08561(3) -0.03426(5) 0.61872(4) 0.01308(9) Uani 1 1 d . . . . .
N4 N 0.02730(4) -0.15455(6) 0.50961(4) 0.01654(11) Uani 1 1 d . . . . .
H4 H 0.0642 -0.1439 0.4875 0.020 Uiso 1 1 calc R U . . .
C1 C 0.12026(5) 0.15145(6) 0.80854(5) 0.01745(12) Uani 1 1 d . . . . .
C2 C 0.13269(4) 0.08955(6) 0.73238(5) 0.01350(11) Uani 1 1 d . . . . .
C3 C 0.20195(4) 0.12419(7) 0.72302(5) 0.01558(11) Uani 1 1 d . . . . .
C4 C 0.22816(5) 0.20332(7) 0.79223(5) 0.01820(13) Uani 1 1 d . . . . .
C5 C 0.24289(5) 0.09523(9) 0.66522(6) 0.02282(15) Uani 1 1 d . . . . .
H5 H 0.2260 0.0415 0.6187 0.027 Uiso 1 1 calc R U . . .
C6 C 0.30969(5) 0.14757(11) 0.67759(8) 0.02968(19) Uani 1 1 d . . . . .
H6 H 0.3385 0.1296 0.6385 0.036 Uiso 1 1 calc R U . . .
C7 C 0.33473(5) 0.22570(10) 0.74632(7) 0.02793(18) Uani 1 1 d . . . . .
H7 H 0.3804 0.2598 0.7533 0.034 Uiso 1 1 calc R U . . .
C8 C 0.29432(5) 0.25499(8) 0.80506(6) 0.02350(16) Uani 1 1 d . . . . .
H8 H 0.3115 0.3082 0.8519 0.028 Uiso 1 1 calc R U . . .
C9 C 0.02677(4) -0.10114(6) 0.58532(4) 0.01257(10) Uani 1 1 d . . . . .
C10 C -0.02956(5) -0.22916(7) 0.46174(5) 0.02021(14) Uani 1 1 d . . . . .
H10A H -0.0225 -0.2483 0.4029 0.030 Uiso 1 1 calc R U . . .
H10B H -0.0764 -0.1923 0.4526 0.030 Uiso 1 1 calc R U . . .
H10C H -0.0283 -0.2974 0.4973 0.030 Uiso 1 1 calc R U . . .
O16 O 0.31249(18) 0.1060(3) 1.0343(2) 0.0398(4) Uani 0.421(2) 1 d D . P A 1
N17 N 0.31003(14) -0.0219(2) 0.92483(19) 0.0219(3) Uani 0.421(2) 1 d D . P A 1
C18 C 0.33944(18) 0.0624(3) 0.9789(2) 0.0263(4) Uani 0.421(2) 1 d D . P A 1
H18 H 0.3843 0.0909 0.9745 0.032 Uiso 0.421(2) 1 calc R U P A 1
C19 C 0.23892(17) -0.0631(4) 0.9237(3) 0.0272(4) Uani 0.421(2) 1 d D . P A 1
H19A H 0.2434 -0.1377 0.9510 0.041 Uiso 0.421(2) 1 calc R U P A 1
H19B H 0.2085 -0.0672 0.8611 0.041 Uiso 0.421(2) 1 calc R U P A 1
H19C H 0.2169 -0.0123 0.9584 0.041 Uiso 0.421(2) 1 calc R U P A 1
C20 C 0.3445(3) -0.0695(4) 0.8604(3) 0.0363(5) Uani 0.421(2) 1 d D . P A 1
H20A H 0.3168 -0.0496 0.7988 0.054 Uiso 0.421(2) 1 calc R U P A 1
H20B H 0.3464 -0.1509 0.8668 0.054 Uiso 0.421(2) 1 calc R U P A 1
H20C H 0.3936 -0.0399 0.8724 0.054 Uiso 0.421(2) 1 calc R U P A 1
O16A O 0.28257(13) 0.12185(18) 1.03044(15) 0.0398(4) Uani 0.579(2) 1 d D . P A
2
N17A N 0.29081(10) -0.02068(15) 0.93735(13) 0.0219(3) Uani 0.579(2) 1 d D . P A
2
C18A C 0.31636(13) 0.06784(17) 0.98821(15) 0.0263(4) Uani 0.579(2) 1 d D . P A
2
H18A H 0.3642 0.0909 0.9921 0.032 Uiso 0.579(2) 1 calc R U P A 2
C19A C 0.21775(13) -0.0610(3) 0.9272(2) 0.0272(4) Uani 0.579(2) 1 d D . P A 2
H19D H 0.2197 -0.1323 0.9591 0.041 Uiso 0.579(2) 1 calc R U P A 2
H19E H 0.1931 -0.0716 0.8628 0.041 Uiso 0.579(2) 1 calc R U P A 2
H19F H 0.1912 -0.0062 0.9529 0.041 Uiso 0.579(2) 1 calc R U P A 2
C20A C 0.33204(17) -0.0779(3) 0.8851(2) 0.0363(5) Uani 0.579(2) 1 d D . P A 2
H20D H 0.3105 -0.0632 0.8206 0.054 Uiso 0.579(2) 1 calc R U P A 2
H20E H 0.3315 -0.1585 0.8963 0.054 Uiso 0.579(2) 1 calc R U P A 2
H20F H 0.3819 -0.0508 0.9032 0.054 Uiso 0.579(2) 1 calc R U P A 2
O20 O 0.02188(11) 0.52758(17) 0.91454(14) 0.0389(4) Uani 0.5 1 d . . P B -1
C21 C 0.00686(18) 0.5763(6) 0.8277(4) 0.0324(6) Uani 0.5 1 d . . P B -1
H21 H -0.0065 0.6526 0.8175 0.039 Uiso 0.5 1 calc R U P B -1
N22 N 0.01226(10) 0.51268(12) 0.76413(16) 0.0249(4) Uani 0.5 1 d D . P B -1
C23 C 0.0326(2) 0.39572(19) 0.7693(2) 0.0447(7) Uani 0.5 1 d D . P B -1
H23A H 0.0431 0.3702 0.8321 0.067 Uiso 0.5 1 calc R U P B -1
H23B H 0.0756 0.3864 0.7480 0.067 Uiso 0.5 1 calc R U P B -1
H23C H -0.0072 0.3516 0.7312 0.067 Uiso 0.5 1 calc R U P B -1
C24 C -0.00759(18) 0.5583(7) 0.6659(4) 0.0324(6) Uani 0.5 1 d D . P B -1
H24A H -0.0487 0.5163 0.6284 0.049 Uiso 0.5 1 calc R U P B -1
H24B H 0.0338 0.5498 0.6413 0.049 Uiso 0.5 1 calc R U P B -1
H24C H -0.0204 0.6374 0.6660 0.049 Uiso 0.5 1 calc R U P B -1


_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 S1 2.3671(3) . ?
Ni1 S1 2.3671(3) 2_556 ?
Ni1 O1 2.2121(7) 2_556 ?
Ni1 O1 2.2121(7) . ?
Ni1 N2 2.0161(7) . ?
Ni1 N2 2.0162(6) 2_556 ?
S1 C9 1.7098(7) . ?
O1 C1 1.2495(11) . ?
N1 H1 0.8800 . ?
N1 C1 1.3523(11) . ?
N1 C4 1.3984(12) . ?
N2 N3 1.3229(9) . ?
N2 C2 1.3084(10) . ?
N3 C9 1.3674(10) . ?
N4 H4 0.8800 . ?
N4 C9 1.3314(9) . ?
N4 C10 1.4471(11) . ?
C1 C2 1.4618(10) . ?
C2 C3 1.4445(11) . ?
C3 C4 1.4098(11) . ?
C3 C5 1.3882(12) . ?
C4 C8 1.3825(12) . ?
C5 H5 0.9500 . ?
C5 C6 1.3979(14) . ?
C6 H6 0.9500 . ?
C6 C7 1.3937(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3931(16) . ?
C8 H8 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
O16 C18 1.231(3) . ?
N17 C18 1.330(3) . ?
N17 C19 1.454(3) . ?
N17 C20 1.455(3) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O16A C18A 1.226(3) . ?
N17A C18A 1.328(2) . ?
N17A C19A 1.457(3) . ?
N17A C20A 1.451(3) . ?
C18A H18A 0.9500 . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
O20 C21 1.413(4) . ?
C21 H21 0.9500 . ?
C21 N22 1.266(9) . ?
N22 C23 1.451(3) . ?
N22 C24 1.551(8) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
S1 Ni1 S1 97.074(13) . 2_556 ?
O1 Ni1 S1 89.82(2) 2_556 . ?
O1 Ni1 S1 161.785(17) . . ?
O1 Ni1 S1 89.82(2) . 2_556 ?
O1 Ni1 S1 161.785(17) 2_556 2_556 ?
O1 Ni1 O1 88.74(4) . 2_556 ?
N2 Ni1 S1 103.466(18) . 2_556 ?
N2 Ni1 S1 81.231(19) 2_556 2_556 ?
N2 Ni1 S1 81.231(19) . . ?
N2 Ni1 S1 103.467(18) 2_556 . ?
N2 Ni1 O1 80.77(2) . . ?
N2 Ni1 O1 94.22(2) 2_556 . ?
N2 Ni1 O1 94.22(2) . 2_556 ?
N2 Ni1 O1 80.77(2) 2_556 2_556 ?
N2 Ni1 N2 173.04(4) . 2_556 ?
C9 S1 Ni1 94.87(3) . . ?
C1 O1 Ni1 104.81(5) . . ?
C1 N1 H1 125.0 . . ?
C1 N1 C4 109.97(7) . . ?
C4 N1 H1 125.0 . . ?
N3 N2 Ni1 126.14(5) . . ?
C2 N2 Ni1 113.81(5) . . ?
C2 N2 N3 120.05(6) . . ?
N2 N3 C9 111.56(6) . . ?
C9 N4 H4 118.2 . . ?
C9 N4 C10 123.52(7) . . ?
C10 N4 H4 118.2 . . ?
O1 C1 N1 127.75(7) . . ?
O1 C1 C2 124.79(7) . . ?
N1 C1 C2 107.46(7) . . ?
N2 C2 C1 115.57(7) . . ?
N2 C2 C3 137.13(7) . . ?
C3 C2 C1 107.31(6) . . ?
C4 C3 C2 105.36(7) . . ?
C5 C3 C2 134.41(8) . . ?
C5 C3 C4 120.22(8) . . ?
N1 C4 C3 109.90(7) . . ?
C8 C4 N1 128.00(8) . . ?
C8 C4 C3 122.10(8) . . ?
C3 C5 H5 121.0 . . ?
C3 C5 C6 117.96(9) . . ?
C6 C5 H5 121.0 . . ?
C5 C6 H6 119.5 . . ?
C7 C6 C5 121.05(10) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 H7 119.2 . . ?
C8 C7 C6 121.52(9) . . ?
C8 C7 H7 119.2 . . ?
C4 C8 C7 117.16(9) . . ?
C4 C8 H8 121.4 . . ?
C7 C8 H8 121.4 . . ?
N3 C9 S1 126.10(5) . . ?
N4 C9 S1 120.19(6) . . ?
N4 C9 N3 113.71(6) . . ?
N4 C10 H10A 109.5 . . ?
N4 C10 H10B 109.5 . . ?
N4 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C18 N17 C19 120.1(3) . . ?
C18 N17 C20 121.8(3) . . ?
C19 N17 C20 117.9(3) . . ?
O16 C18 N17 124.4(3) . . ?
O16 C18 H18 117.8 . . ?
N17 C18 H18 117.8 . . ?
N17 C19 H19A 109.5 . . ?
N17 C19 H19B 109.5 . . ?
N17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N17 C20 H20A 109.5 . . ?
N17 C20 H20B 109.5 . . ?
N17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18A N17A C19A 121.11(19) . . ?
C18A N17A C20A 122.2(2) . . ?
C20A N17A C19A 116.6(2) . . ?
O16A C18A N17A 124.6(2) . . ?
O16A C18A H18A 117.7 . . ?
N17A C18A H18A 117.7 . . ?
N17A C19A H19D 109.5 . . ?
N17A C19A H19E 109.5 . . ?
N17A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
N17A C20A H20D 109.5 . . ?
N17A C20A H20E 109.5 . . ?
N17A C20A H20F 109.5 . . ?
H20D C20A H20E 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
O20 C21 H21 121.9 . . ?
N22 C21 O20 116.3(5) . . ?
N22 C21 H21 121.9 . . ?
C21 N22 C23 128.2(3) . . ?
C21 N22 C24 119.28(19) . . ?
C23 N22 C24 112.5(3) . . ?
N22 C23 H23A 109.5 . . ?
N22 C23 H23B 109.5 . . ?
N22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N22 C24 H24A 109.5 . . ?
N22 C24 H24B 109.5 . . ?
N22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
Ni1 S1 C9 N3 3.66(6) . . . . ?
Ni1 S1 C9 N4 -176.70(6) . . . . ?
Ni1 O1 C1 N1 -177.27(8) . . . . ?
Ni1 O1 C1 C2 3.49(10) . . . . ?
Ni1 N2 N3 C9 0.68(8) . . . . ?
Ni1 N2 C2 C1 -4.01(8) . . . . ?
Ni1 N2 C2 C3 176.68(8) . . . . ?
O1 C1 C2 N2 -0.02(12) . . . . ?
O1 C1 C2 C3 179.48(8) . . . . ?
N1 C1 C2 N2 -179.39(7) . . . . ?
N1 C1 C2 C3 0.11(9) . . . . ?
N1 C4 C8 C7 179.92(9) . . . . ?
N2 N3 C9 S1 -3.32(9) . . . . ?
N2 N3 C9 N4 177.02(6) . . . . ?
N2 C2 C3 C4 179.53(9) . . . . ?
N2 C2 C3 C5 -1.49(16) . . . . ?
N3 N2 C2 C1 176.41(6) . . . . ?
N3 N2 C2 C3 -2.90(13) . . . . ?
C1 N1 C4 C3 0.51(10) . . . . ?
C1 N1 C4 C8 -179.40(9) . . . . ?
C1 C2 C3 C4 0.19(8) . . . . ?
C1 C2 C3 C5 179.17(9) . . . . ?
C2 N2 N3 C9 -179.80(6) . . . . ?
C2 C3 C4 N1 -0.42(9) . . . . ?
C2 C3 C4 C8 179.50(8) . . . . ?
C2 C3 C5 C6 -179.48(9) . . . . ?
C3 C4 C8 C7 0.02(13) . . . . ?
C3 C5 C6 C7 0.56(16) . . . . ?
C4 N1 C1 O1 -179.72(9) . . . . ?
C4 N1 C1 C2 -0.37(10) . . . . ?
C4 C3 C5 C6 -0.61(13) . . . . ?
C5 C3 C4 N1 -179.58(8) . . . . ?
C5 C3 C4 C8 0.34(12) . . . . ?
C5 C6 C7 C8 -0.21(17) . . . . ?
C6 C7 C8 C4 -0.09(15) . . . . ?
C10 N4 C9 S1 0.79(11) . . . . ?
C10 N4 C9 N3 -179.52(7) . . . . ?
C19 N17 C18 O16 4.7(6) . . . . ?
C20 N17 C18 O16 179.7(4) . . . . ?
C19A N17A C18A O16A 0.5(4) . . . . ?
C20A N17A C18A O16A 176.8(3) . . . . ?
O20 C21 N22 C23 -0.6(5) . . . . ?
O20 C21 N22 C24 176.5(3) . . . . ?

