# Electronic Supplementary Material (ESI) for MedChemComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1852751'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.
2018-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 N3 S'
_chemical_formula_weight         193.27

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'
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                   13.2482(9)
_cell_length_b                   8.2243(4)
_cell_length_c                   10.2827(7)
_cell_angle_alpha                90
_cell_angle_beta                 111.265(3)
_cell_angle_gamma                90
_cell_volume                     1044.09(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2561
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      28.19

_exptl_crystal_description       sheet
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.230
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.269
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.90
_exptl_absorpt_process_details   'SADABS (Bruer, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker AXS Kappa Apex2 CMOS diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4683
_diffrn_reflns_av_unetI/netI     0.0778
_diffrn_reflns_av_R_equivalents  0.0621
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.976
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             1803
_reflns_number_gt                1094
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1803
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1115
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1270
_refine_ls_wR_factor_gt          0.1069
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_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
C1 C 0.0756(2) 0.4066(4) 0.3638(3) 0.0366(7) Uani 1 1 d . . . . .
C2 C 0.1847(2) 0.6844(4) 0.6336(3) 0.0394(8) Uani 1 1 d . . . . .
H2 H 0.156435 0.777384 0.581726 0.047 Uiso 1 1 calc R U . . .
C3 C 0.2568(2) 0.7016(4) 0.7771(3) 0.0381(8) Uani 1 1 d . . . . .
C4 C 0.2945(3) 0.8546(4) 0.8304(4) 0.0452(9) Uani 1 1 d . . . . .
H4 H 0.267678 0.946181 0.775666 0.054 Uiso 1 1 calc R U . . .
C5 C 0.3706(3) 0.8731(4) 0.9623(4) 0.0492(9) Uani 1 1 d . . . . .
H5 H 0.393775 0.976999 0.995473 0.059 Uiso 1 1 calc R U . . .
C6 C 0.4132(3) 0.7412(5) 1.0462(3) 0.0498(9) Uani 1 1 d . . . . .
C7 C 0.3732(3) 0.5882(4) 0.9948(3) 0.0562(10) Uani 1 1 d . . . . .
H7 H 0.399158 0.497406 1.050884 0.067 Uiso 1 1 calc R U . . .
C8 C 0.2967(3) 0.5679(4) 0.8644(3) 0.0494(9) Uani 1 1 d . . . . .
H8 H 0.271130 0.464205 0.833549 0.059 Uiso 1 1 calc R U . . .
C9 C 0.5002(3) 0.7603(5) 1.1888(4) 0.0706(12) Uani 1 1 d . . . . .
H9A H 0.545563 0.851132 1.188105 0.106 Uiso 1 1 calc R U . . .
H9B H 0.543271 0.663207 1.212407 0.106 Uiso 1 1 calc R U . . .
H9C H 0.467193 0.778793 1.256562 0.106 Uiso 1 1 calc R U . . .
N1 N 0.1048(2) 0.2701(3) 0.4375(3) 0.0583(9) Uani 1 1 d . . . . .
H1A H 0.136216 0.274468 0.526700 0.070 Uiso 1 1 calc R U . . .
H1B H 0.092203 0.177436 0.395821 0.070 Uiso 1 1 calc R U . . .
N2 N 0.0980(2) 0.5460(3) 0.4360(3) 0.0388(7) Uani 1 1 d . . . . .
H2A H 0.074011 0.636488 0.394220 0.047 Uiso 1 1 calc R U . . .
N3 N 0.15874(19) 0.5456(3) 0.5761(3) 0.0360(7) Uani 1 1 d . . . . .
S1 S 0.01729(8) 0.40983(9) 0.18825(8) 0.0474(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0414(19) 0.0404(18) 0.0280(19) 0.0018(15) 0.0128(15) -0.0001(16)
C2 0.0400(19) 0.0399(19) 0.036(2) -0.0015(15) 0.0112(16) 0.0006(15)
C3 0.0323(18) 0.050(2) 0.030(2) -0.0049(15) 0.0082(16) -0.0021(15)
C4 0.045(2) 0.048(2) 0.041(2) -0.0061(16) 0.0146(18) -0.0013(16)
C5 0.047(2) 0.058(2) 0.041(2) -0.0151(18) 0.0139(18) -0.0081(18)
C6 0.0373(19) 0.080(3) 0.031(2) -0.0099(19) 0.0104(17) -0.0090(19)
C7 0.059(2) 0.066(2) 0.033(2) 0.0055(18) 0.0042(19) 0.000(2)
C8 0.053(2) 0.046(2) 0.042(2) -0.0034(16) 0.0080(19) -0.0049(17)
C9 0.056(2) 0.106(3) 0.040(3) -0.013(2) 0.006(2) -0.013(2)
N1 0.095(2) 0.0365(16) 0.0311(18) 0.0004(13) 0.0083(17) 0.0019(15)
N2 0.0527(17) 0.0310(14) 0.0295(16) -0.0016(11) 0.0110(14) -0.0009(12)
N3 0.0402(16) 0.0413(16) 0.0234(16) -0.0024(11) 0.0076(13) -0.0042(12)
S1 0.0702(6) 0.0388(5) 0.0279(5) -0.0036(4) 0.0115(4) -0.0058(5)

_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
C1 N1 1.331(3) . ?
C1 N2 1.340(3) . ?
C1 S1 1.686(3) . ?
C2 N3 1.274(4) . ?
C2 C3 1.444(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(4) . ?
C3 C8 1.397(4) . ?
C4 C5 1.374(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.373(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(4) . ?
C6 C9 1.509(4) . ?
C7 C8 1.366(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N2 N3 1.372(3) . ?
N2 H2A 0.8600 . ?

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 C1 N2 116.5(3) . . ?
N1 C1 S1 123.2(2) . . ?
N2 C1 S1 120.2(2) . . ?
N3 C2 C3 122.0(3) . . ?
N3 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?
C4 C3 C8 117.4(3) . . ?
C4 C3 C2 120.0(3) . . ?
C8 C3 C2 122.4(3) . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
C5 C6 C7 117.5(3) . . ?
C5 C6 C9 121.5(3) . . ?
C7 C6 C9 121.0(3) . . ?
C8 C7 C6 121.9(3) . . ?
C8 C7 H7 119.1 . . ?
C6 C7 H7 119.1 . . ?
C7 C8 C3 120.5(3) . . ?
C7 C8 H8 119.7 . . ?
C3 C8 H8 119.7 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C1 N2 N3 120.5(2) . . ?
C1 N2 H2A 119.8 . . ?
N3 N2 H2A 119.8 . . ?
C2 N3 N2 116.2(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
N3 C2 C3 C4 171.4(3) . . . . ?
N3 C2 C3 C8 -4.4(5) . . . . ?
C8 C3 C4 C5 1.9(5) . . . . ?
C2 C3 C4 C5 -174.0(3) . . . . ?
C3 C4 C5 C6 0.7(5) . . . . ?
C4 C5 C6 C7 -2.6(5) . . . . ?
C4 C5 C6 C9 177.4(3) . . . . ?
C5 C6 C7 C8 2.0(5) . . . . ?
C9 C6 C7 C8 -178.0(3) . . . . ?
C6 C7 C8 C3 0.6(5) . . . . ?
C4 C3 C8 C7 -2.5(5) . . . . ?
C2 C3 C8 C7 173.3(3) . . . . ?
N1 C1 N2 N3 7.2(5) . . . . ?
S1 C1 N2 N3 -170.8(2) . . . . ?
C3 C2 N3 N2 -174.1(3) . . . . ?
C1 N2 N3 C2 173.6(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
N1 H1B S1 0.86 2.60 3.398(3) 153.9 2_545
N2 H2A S1 0.86 2.55 3.391(2) 166.9 2

_refine_diff_density_max         0.171
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.051

_shelx_res_file                  
;
TITL Sb4_0ma_a.res in P2(1)/c
    shelx.res
    created by SHELXL-2016/6 at 14:49:21 on 30-Apr-2018
REM Old TITL Sb4_0ma in P2(1)/c
REM SHELXT solution in P2(1)/c
REM R1 0.224, Rweak 0.029, Alpha 0.049, Orientation as input
REM Formula found by SHELXT: C9 N3 S
CELL 0.71073 13.2482 8.2243 10.2827 90 111.265 90
ZERR 4 0.0009 0.0004 0.0007 0 0.003 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H N S
UNIT 36 44 12 4
CONF
HTAB
EQIV $1 -x, y-1/2, -z+1/2
HTAB N1 S1_$1
EQIV $2 -x, y+1/2, -z+1/2
HTAB N2 S1_$2
L.S. 10
PLAN  1
SIZE 0.03 0.4 0.4
TEMP 23
BOND $H
fmap 2
acta
OMIT -3 50
REM <olex2.extras>
REM <HklSrc "%.\\Sb4_0ma_a.hkl">
REM </olex2.extras>

WGHT    0.052800
FVAR       0.48708
C1    1    0.075643    0.406601    0.363772    11.00000    0.04145    0.04042 =
         0.02798    0.00178    0.01282   -0.00006
C2    1    0.184711    0.684409    0.633636    11.00000    0.03997    0.03989 =
         0.03601   -0.00153    0.01116    0.00062
AFIX  43
H2    2    0.156435    0.777384    0.581726    11.00000   -1.20000
AFIX   0
C3    1    0.256758    0.701605    0.777125    11.00000    0.03232    0.04995 =
         0.02956   -0.00485    0.00819   -0.00212
C4    1    0.294494    0.854619    0.830390    11.00000    0.04541    0.04826 =
         0.04100   -0.00613    0.01455   -0.00127
AFIX  43
H4    2    0.267678    0.946181    0.775666    11.00000   -1.20000
AFIX   0
C5    1    0.370632    0.873079    0.962314    11.00000    0.04703    0.05820 =
         0.04079   -0.01513    0.01390   -0.00811
AFIX  43
H5    2    0.393775    0.976999    0.995473    11.00000   -1.20000
AFIX   0
C6    1    0.413245    0.741195    1.046189    11.00000    0.03734    0.07984 =
         0.03056   -0.00991    0.01040   -0.00904
C7    1    0.373163    0.588238    0.994831    11.00000    0.05902    0.06639 =
         0.03284    0.00549    0.00421   -0.00047
AFIX  43
H7    2    0.399158    0.497406    1.050884    11.00000   -1.20000
AFIX   0
C8    1    0.296736    0.567889    0.864428    11.00000    0.05266    0.04554 =
         0.04244   -0.00340    0.00805   -0.00488
AFIX  43
H8    2    0.271130    0.464205    0.833549    11.00000   -1.20000
AFIX   0
C9    1    0.500230    0.760321    1.188785    11.00000    0.05622    0.10572 =
         0.04024   -0.01321    0.00580   -0.01287
AFIX 137
H9A   2    0.545563    0.851132    1.188105    11.00000   -1.50000
H9B   2    0.543271    0.663207    1.212407    11.00000   -1.50000
H9C   2    0.467193    0.778793    1.256562    11.00000   -1.50000
AFIX   0
N1    3    0.104793    0.270058    0.437458    11.00000    0.09523    0.03646 =
         0.03107    0.00036    0.00831    0.00187
AFIX  93
H1A   2    0.136216    0.274468    0.526700    11.00000   -1.20000
H1B   2    0.092203    0.177436    0.395821    11.00000   -1.20000
AFIX   0
N2    3    0.097963    0.546042    0.435985    11.00000    0.05268    0.03095 =
         0.02947   -0.00161    0.01097   -0.00087
AFIX  43
H2A   2    0.074011    0.636488    0.394220    11.00000   -1.20000
AFIX   0
N3    3    0.158743    0.545611    0.576060    11.00000    0.04018    0.04132 =
         0.02335   -0.00239    0.00760   -0.00419
S1    4    0.017290    0.409826    0.188247    11.00000    0.07021    0.03885 =
         0.02794   -0.00356    0.01153   -0.00576
HKLF 4




REM  Sb4_0ma_a.res in P2(1)/c
REM R1 =  0.0558 for    1094 Fo > 4sig(Fo)  and  0.1115 for all    1803 data
REM    119 parameters refined using      0 restraints

END

WGHT      0.0532      0.0000

REM Instructions for potential hydrogen bonds
HTAB N1 S1_$1
HTAB N2 S1_$2

REM Highest difference peak  0.171,  deepest hole -0.230,  1-sigma level  0.051
Q1    1   0.2210  0.6044  0.9210  11.00000  0.05    0.17
;
_shelx_res_checksum              64352
