# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_f
_database_code_depnum_ccdc_archive 'CCDC 1475312'
_audit_update_record             
;
2016-04-20 deposited with the CCDC.
2018-04-30 downloaded from the CCDC.
;
_audit_creation_date             2016-04-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        'Hydroxy thiosemicarbazide derivative'
_chemical_formula_moiety         'C9 H11 N3 O S'
_chemical_formula_sum            'C9 H11 N3 O S'
_chemical_formula_weight         209.27
_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                   6.885(3)
_cell_length_b                   7.108(3)
_cell_length_c                   11.230(4)
_cell_angle_alpha                74.336(4)
_cell_angle_beta                 76.662(4)
_cell_angle_gamma                73.802(4)
_cell_volume                     500.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2105
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.477
_cell_measurement_theta_min      3.059
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6360
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.0450 before and 0.0355 after correction.
The Ratio of minimum to maximum transmission is 0.8530.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             220
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4355
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_min         1.910
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1928
_reflns_number_total             2227
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.049
_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)+(0.0552P)²+0.1465P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0998
_refine_ls_wR_factor_ref         0.1042
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C5(H5), C6(H6)
2.b X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_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
S1 S 0.28281(6) 0.26829(6) -0.06621(4) 0.02164(15) Uani 1 1 d . . . . .
O1 O 0.70931(18) 0.29306(19) 0.73936(11) 0.0241(3) Uani 1 1 d . . . . .
H1 H 0.5969 0.2873 0.7875 0.036 Uiso 1 1 calc GR . . . .
N1 N 0.5105(2) 0.2558(2) 0.22599(12) 0.0195(3) Uani 1 1 d . . . . .
N2 N 0.4945(2) 0.2211(2) 0.11301(12) 0.0205(3) Uani 1 1 d . . . . .
H2 H 0.5926 0.1374 0.0748 0.025 Uiso 1 1 calc R . . . .
N3 N 0.1932(2) 0.4561(2) 0.12159(13) 0.0222(3) Uani 1 1 d . . . . .
H3A H 0.2199 0.4790 0.1887 0.027 Uiso 1 1 calc R . . . .
H3B H 0.0795 0.5241 0.0926 0.027 Uiso 1 1 calc R . . . .
C1 C 0.6927(2) 0.2221(2) 0.38535(14) 0.0166(3) Uani 1 1 d . . . . .
C2 C 0.8711(2) 0.2404(2) 0.41622(15) 0.0207(4) Uani 1 1 d . . . . .
H2A H 0.9933 0.2336 0.3558 0.025 Uiso 1 1 calc R . . . .
C3 C 0.8727(2) 0.2682(3) 0.53316(15) 0.0220(4) Uani 1 1 d . . . . .
H3 H 0.9943 0.2841 0.5516 0.026 Uiso 1 1 calc R . . . .
C4 C 0.6967(2) 0.2730(2) 0.62375(14) 0.0179(3) Uani 1 1 d . . . . .
C5 C 0.5172(2) 0.2562(2) 0.59510(15) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.3959 0.2608 0.6563 0.023 Uiso 1 1 calc R . . . .
C6 C 0.5161(2) 0.2326(2) 0.47727(15) 0.0184(3) Uani 1 1 d . . . . .
H6 H 0.3922 0.2233 0.4580 0.022 Uiso 1 1 calc R . . . .
C7 C 0.6869(2) 0.1914(2) 0.26109(15) 0.0177(3) Uani 1 1 d . . . . .
C8 C 0.8770(2) 0.0883(3) 0.18678(16) 0.0248(4) Uani 1 1 d . . . . .
H8A H 0.8686 -0.0489 0.1914 0.037 Uiso 1 1 calc GR . . . .
H8B H 0.9970 0.0840 0.2212 0.037 Uiso 1 1 calc GR . . . .
H8C H 0.8898 0.1622 0.0991 0.037 Uiso 1 1 calc GR . . . .
C9 C 0.3238(2) 0.3198(2) 0.06451(14) 0.0177(3) 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 1.7053(17) . ?
O1 H1 0.8400 . ?
O1 C4 1.3683(19) . ?
N1 N2 1.3897(19) . ?
N1 C7 1.286(2) . ?
N2 H2 0.8800 . ?
N2 C9 1.341(2) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C9 1.320(2) . ?
C1 C2 1.399(2) . ?
C1 C6 1.400(2) . ?
C1 C7 1.480(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.383(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(2) . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.496(2) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C4 O1 H1 109.5 . . ?
C7 N1 N2 117.52(14) . . ?
N1 N2 H2 121.3 . . ?
C9 N2 N1 117.48(13) . . ?
C9 N2 H2 121.3 . . ?
H3A N3 H3B 120.0 . . ?
C9 N3 H3A 120.0 . . ?
C9 N3 H3B 120.0 . . ?
C2 C1 C6 117.54(14) . . ?
C2 C1 C7 122.26(14) . . ?
C6 C1 C7 120.20(14) . . ?
C1 C2 H2A 119.4 . . ?
C3 C2 C1 121.15(14) . . ?
C3 C2 H2A 119.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.14(15) . . ?
C4 C3 H3 119.9 . . ?
O1 C4 C3 117.62(14) . . ?
O1 C4 C5 122.62(14) . . ?
C3 C4 C5 119.76(15) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.63(14) . . ?
C6 C5 H5 120.2 . . ?
C1 C6 H6 119.1 . . ?
C5 C6 C1 121.75(15) . . ?
C5 C6 H6 119.1 . . ?
N1 C7 C1 115.28(14) . . ?
N1 C7 C8 124.54(15) . . ?
C1 C7 C8 120.18(14) . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N2 C9 S1 120.14(12) . . ?
N3 C9 S1 122.56(12) . . ?
N3 C9 N2 117.30(14) . . ?

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
O1 H1 S1 0.84 2.41 3.2470(16) 177.3 1_556
N2 H2 S1 0.88 2.79 3.5165(19) 140.6 2_655
N3 H3A O1 0.88 2.20 2.9533(19) 143.2 2_666
N3 H3B S1 0.88 2.56 3.4157(18) 165.3 2_565

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
O1 C4 C5 C6 -178.82(14) . . . . ?
N1 N2 C9 S1 -174.12(11) . . . . ?
N1 N2 C9 N3 6.2(2) . . . . ?
N2 N1 C7 C1 -176.66(12) . . . . ?
N2 N1 C7 C8 2.2(2) . . . . ?
C1 C2 C3 C4 1.8(2) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C2 C1 C7 N1 -153.10(16) . . . . ?
C2 C1 C7 C8 28.0(2) . . . . ?
C2 C3 C4 O1 177.48(14) . . . . ?
C2 C3 C4 C5 -2.1(2) . . . . ?
C3 C4 C5 C6 0.7(2) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C7 N1 27.2(2) . . . . ?
C6 C1 C7 C8 -151.64(16) . . . . ?
C7 N1 N2 C9 -167.55(15) . . . . ?
C7 C1 C2 C3 -179.77(15) . . . . ?
C7 C1 C6 C5 178.39(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method Acetonitrile
