# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_mkcd1_0m
_database_code_depnum_ccdc_archive 'CCDC 1550501'
_audit_update_record             
;
2017-05-16 deposited with the CCDC.
2017-06-14 downloaded from the CCDC.
;
_audit_creation_date             2017-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H4 N4 O S, C3 H7 N O'
_chemical_formula_sum            'C9 H11 N5 O2 S'
_chemical_formula_weight         253.29
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.5656(3)
_cell_length_b                   8.5877(4)
_cell_length_c                   12.2172(7)
_cell_angle_alpha                95.751(4)
_cell_angle_beta                 98.795(3)
_cell_angle_gamma                101.942(3)
_cell_volume                     559.30(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1548
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.785
_cell_measurement_theta_min      2.784
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.943
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9433
_exptl_absorpt_correction_T_max  0.9790
_exptl_absorpt_process_details   
;
 TWINABS-2008/4 (Bruker,2010) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0434 before and 0.0365 after correction.
 The Ratio of minimum to maximum transmission is 0.92.
Final HKLF 4 output contains 16610 reflections, Rint = 0.0619
 (3325 with I > 3sig(I), Rint = 0.0227)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.074
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0269
_diffrn_reflns_av_unetI/netI     0.0408
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5627
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.409
_diffrn_reflns_theta_min         3.880
_diffrn_ambient_temperature      172.99
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.991
_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                1731
_reflns_number_total             2269
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     162
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+0.0961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0964
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C7(H7)
2.b Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.059
;
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 1.33643(10) 0.37851(7) 0.33761(5) 0.03322(18) Uani 1 1 d . . . . .
O1 O 1.1257(2) 0.77919(16) 0.10187(12) 0.0302(4) Uani 1 1 d . . . . .
O2 O -0.3303(3) 0.77601(18) 0.29449(13) 0.0362(4) Uani 1 1 d . . . . .
N1 N 0.8280(3) 0.1846(2) 0.20933(14) 0.0284(4) Uani 1 1 d . . . . .
N2 N 0.5121(3) 0.3192(2) 0.06404(13) 0.0250(4) Uani 1 1 d . . . . .
N3 N 0.8213(3) 0.5522(2) 0.08759(14) 0.0242(4) Uani 1 1 d . . . . .
H3 H 0.733(4) 0.593(3) 0.0475(18) 0.029 Uiso 1 1 d R . . . .
N4 N 1.2043(3) 0.5813(2) 0.20430(14) 0.0240(4) Uani 1 1 d . . . . .
H4 H 1.353(4) 0.647(3) 0.2318(18) 0.029 Uiso 1 1 d R . . . .
N5 N 0.0453(3) 0.8128(2) 0.40900(14) 0.0257(4) Uani 1 1 d . . . . .
C1 C 0.8978(3) 0.3356(2) 0.18722(16) 0.0230(4) Uani 1 1 d . . . . .
C2 C 0.6020(4) 0.1028(3) 0.15866(17) 0.0305(5) Uani 1 1 d . . . . .
H2 H 0.546642 -0.005222 0.171060 0.037 Uiso 1 1 calc R . . . .
C3 C 0.4439(4) 0.1706(2) 0.08800(17) 0.0282(5) Uani 1 1 d . . . . .
H3A H 0.281836 0.108542 0.055834 0.034 Uiso 1 1 calc R . . . .
C4 C 0.7424(3) 0.4009(2) 0.11345(16) 0.0226(4) Uani 1 1 d . . . . .
C5 C 1.0539(3) 0.6474(2) 0.12890(16) 0.0234(4) Uani 1 1 d . . . . .
C6 C 1.1444(4) 0.4349(2) 0.24082(16) 0.0231(4) Uani 1 1 d . . . . .
C7 C -0.1878(4) 0.7350(3) 0.36867(18) 0.0305(5) Uani 1 1 d . . . . .
H7 H -0.250729 0.640319 0.398970 0.037 Uiso 1 1 calc R . . . .
C8 C 0.1969(4) 0.7563(3) 0.4983(2) 0.0409(6) Uani 1 1 d . . . . .
H8A H 0.097059 0.660930 0.520932 0.061 Uiso 1 1 calc GR . . . .
H8B H 0.253417 0.841178 0.562497 0.061 Uiso 1 1 calc GR . . . .
H8C H 0.342104 0.728956 0.471395 0.061 Uiso 1 1 calc GR . . . .
C9 C 0.1603(4) 0.9573(3) 0.36857(19) 0.0346(5) Uani 1 1 d . . . . .
H9A H 0.043054 0.981205 0.307623 0.052 Uiso 1 1 calc GR . . . .
H9B H 0.311240 0.941659 0.341026 0.052 Uiso 1 1 calc GR . . . .
H9C H 0.204837 1.046966 0.429602 0.052 Uiso 1 1 calc GR . . . .


_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 C6 1.6486(19) . ?
O1 C5 1.215(2) . ?
O2 C7 1.239(2) . ?
N1 C1 1.341(2) . ?
N1 C2 1.330(2) . ?
N2 C3 1.330(2) . ?
N2 C4 1.344(2) . ?
N3 H3 0.80(2) . ?
N3 C4 1.367(2) . ?
N3 C5 1.370(2) . ?
N4 H4 0.89(2) . ?
N4 C5 1.392(2) . ?
N4 C6 1.369(2) . ?
N5 C7 1.323(2) . ?
N5 C8 1.460(2) . ?
N5 C9 1.444(3) . ?
C1 C4 1.393(2) . ?
C1 C6 1.473(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.392(3) . ?
C3 H3A 0.9500 . ?
C7 H7 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 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
C2 N1 C1 116.37(17) . . ?
C3 N2 C4 115.80(16) . . ?
C4 N3 H3 122.0(15) . . ?
C4 N3 C5 123.65(17) . . ?
C5 N3 H3 114.4(15) . . ?
C5 N4 H4 113.4(13) . . ?
C6 N4 H4 119.3(13) . . ?
C6 N4 C5 127.32(16) . . ?
C7 N5 C8 120.93(18) . . ?
C7 N5 C9 122.13(17) . . ?
C9 N5 C8 116.94(16) . . ?
N1 C1 C4 121.36(17) . . ?
N1 C1 C6 119.79(17) . . ?
C4 C1 C6 118.85(17) . . ?
N1 C2 H2 119.0 . . ?
N1 C2 C3 122.03(19) . . ?
C3 C2 H2 119.0 . . ?
N2 C3 C2 122.21(18) . . ?
N2 C3 H3A 118.9 . . ?
C2 C3 H3A 118.9 . . ?
N2 C4 N3 117.23(17) . . ?
N2 C4 C1 122.17(18) . . ?
N3 C4 C1 120.59(17) . . ?
O1 C5 N3 123.09(17) . . ?
O1 C5 N4 122.08(17) . . ?
N3 C5 N4 114.82(17) . . ?
N4 C6 S1 121.60(14) . . ?
N4 C6 C1 114.55(16) . . ?
C1 C6 S1 123.85(15) . . ?
O2 C7 N5 125.1(2) . . ?
O2 C7 H7 117.5 . . ?
N5 C7 H7 117.5 . . ?
N5 C8 H8A 109.5 . . ?
N5 C8 H8B 109.5 . . ?
N5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N5 C9 H9A 109.5 . . ?
N5 C9 H9B 109.5 . . ?
N5 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
N3 H3 N2 0.80(2) 2.09(2) 2.881(2) 175(2) 2_665
N4 H4 O2 0.89(2) 1.88(2) 2.772(2) 177(2) 1_755

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 C1 C4 N2 2.6(3) . . . . ?
N1 C1 C4 N3 -176.73(19) . . . . ?
N1 C1 C6 S1 -6.0(3) . . . . ?
N1 C1 C6 N4 174.32(18) . . . . ?
N1 C2 C3 N2 2.2(3) . . . . ?
C1 N1 C2 C3 -1.1(3) . . . . ?
C2 N1 C1 C4 -1.2(3) . . . . ?
C2 N1 C1 C6 179.40(19) . . . . ?
C3 N2 C4 N3 177.86(19) . . . . ?
C3 N2 C4 C1 -1.5(3) . . . . ?
C4 N2 C3 C2 -0.8(3) . . . . ?
C4 N3 C5 O1 177.0(2) . . . . ?
C4 N3 C5 N4 -2.6(3) . . . . ?
C4 C1 C6 S1 174.54(16) . . . . ?
C4 C1 C6 N4 -5.1(3) . . . . ?
C5 N3 C4 N2 -177.96(18) . . . . ?
C5 N3 C4 C1 1.4(3) . . . . ?
C5 N4 C6 S1 -175.56(16) . . . . ?
C5 N4 C6 C1 4.1(3) . . . . ?
C6 N4 C5 O1 -180.0(2) . . . . ?
C6 N4 C5 N3 -0.4(3) . . . . ?
C6 C1 C4 N2 -177.97(18) . . . . ?
C6 C1 C4 N3 2.7(3) . . . . ?
C8 N5 C7 O2 178.7(2) . . . . ?
C9 N5 C7 O2 -0.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
