# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_No_13_LT
_database_code_depnum_ccdc_archive 'CCDC 1578756'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H15 N3 S'
_chemical_formula_weight         173.28

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   6.6889(7)
_cell_length_b                   20.404(2)
_cell_length_c                   6.7943(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.245(9)
_cell_angle_gamma                90
_cell_volume                     906.19(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3208
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      28.06

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.300
_shelx_estimated_absorpt_T_min   0.889
_shelx_estimated_absorpt_T_max   0.954
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6245
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         4.290
_diffrn_reflns_theta_max         27.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.950
_reflns_number_total             3940
_reflns_number_gt                3277
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_max     0.915
_reflns_Friedel_fraction_full    0.918

_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 (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)+(0.0003P)²+5.7898P] 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_abs_structure_details 
;
 Flack x determined using 1376 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.62(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3940
_refine_ls_number_parameters     223
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.1693
_refine_ls_wR_factor_gt          0.1534
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_restrained_S_all      1.101
_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
S1A S 0.1544(3) 0.18658(13) 0.5456(3) 0.0135(4) Uani 1 1 d . . . . .
N1A N 0.6459(12) 0.1145(5) 0.3847(11) 0.0155(15) Uani 1 1 d D U . . .
H1A H 0.747(11) 0.143(4) 0.409(15) 0.019 Uiso 1 1 d D U . . .
N2A N 0.5062(12) 0.1367(4) 0.5039(11) 0.0134(15) Uani 1 1 d D . . . .
H2A H 0.581(15) 0.141(5) 0.627(9) 0.016 Uiso 1 1 d D U . . .
N4A N 0.2297(12) 0.1099(4) 0.2536(11) 0.0132(15) Uani 1 1 d D . . . .
H4A H 0.126(10) 0.131(4) 0.177(13) 0.016 Uiso 1 1 d D U . . .
C3A C 0.3065(14) 0.1405(5) 0.4244(13) 0.0128(18) Uani 1 1 d . U . . .
C5A C 0.3027(17) 0.0481(5) 0.1666(14) 0.016(2) Uani 1 1 d . . . . .
C6A C 0.4629(16) 0.0124(5) 0.3339(14) 0.0178(19) Uani 1 1 d . . . . .
H6AA H 0.4061 0.0096 0.4568 0.021 Uiso 1 1 calc R U . . .
H6AB H 0.4796 -0.0329 0.2884 0.021 Uiso 1 1 calc R U . . .
C7A C 0.6728(15) 0.0437(5) 0.3901(15) 0.0151(19) Uani 1 1 d . . . . .
H7AA H 0.7500 0.0316 0.2845 0.018 Uiso 1 1 calc R U . . .
C8A C 0.3871(17) 0.0635(5) -0.0203(14) 0.020(2) Uani 1 1 d . . . . .
H8AA H 0.2900 0.0915 -0.1114 0.030 Uiso 1 1 calc R U . . .
H8AB H 0.4071 0.0226 -0.0892 0.030 Uiso 1 1 calc R U . . .
H8AC H 0.5182 0.0864 0.0200 0.030 Uiso 1 1 calc R U . . .
C9A C 0.1139(17) 0.0056(6) 0.1155(15) 0.023(2) Uani 1 1 d . . . . .
H9AA H 0.0034 0.0301 0.0286 0.035 Uiso 1 1 calc R U . . .
H9AB H 0.0714 -0.0069 0.2398 0.035 Uiso 1 1 calc R U . . .
H9AC H 0.1443 -0.0339 0.0451 0.035 Uiso 1 1 calc R U . . .
C10A C 0.7898(17) 0.0165(6) 0.5913(17) 0.027(2) Uani 1 1 d . . . . .
H10A H 0.9324 0.0313 0.6153 0.041 Uiso 1 1 calc R U . . .
H10B H 0.7856 -0.0315 0.5875 0.041 Uiso 1 1 calc R U . . .
H10C H 0.7266 0.0323 0.6999 0.041 Uiso 1 1 calc R U . . .
S1B S 0.8243(3) 0.18609(14) 0.9262(3) 0.0149(4) Uani 1 1 d . . . . .
N1B N 0.3381(12) 0.2581(4) 1.0932(11) 0.0146(15) Uani 1 1 d D U . . .
H1B H 0.214(8) 0.246(4) 1.030(14) 0.018 Uiso 1 1 d D U . . .
N2B N 0.4718(12) 0.2374(5) 0.9696(11) 0.0162(17) Uani 1 1 d D . . . .
H2B H 0.432(16) 0.221(5) 0.848(9) 0.019 Uiso 1 1 d D U . . .
N4B N 0.7503(11) 0.2626(5) 1.2232(11) 0.0163(17) Uani 1 1 d D . . . .
H4B H 0.880(8) 0.257(5) 1.284(15) 0.020 Uiso 1 1 d D U . . .
C3B C 0.6711(13) 0.2305(5) 1.0497(13) 0.0128(18) Uani 1 1 d . . . . .
C5B C 0.6833(14) 0.3240(5) 1.3063(13) 0.0132(19) Uani 1 1 d . . . . .
C6B C 0.5311(14) 0.3596(6) 1.1473(14) 0.018(2) Uani 1 1 d . . . . .
H6BA H 0.5882 0.3627 1.0246 0.022 Uiso 1 1 calc R U . . .
H6BB H 0.5168 0.4048 1.1952 0.022 Uiso 1 1 calc R U . . .
C7B C 0.3149(16) 0.3289(6) 1.0879(16) 0.022(2) Uani 1 1 d . . . . .
H7BA H 0.2421 0.3406 1.1973 0.027 Uiso 1 1 calc R U . . .
C8B C 0.6013(16) 0.3097(5) 1.4946(14) 0.019(2) Uani 1 1 d . . . . .
H8BA H 0.4942 0.2762 1.4641 0.029 Uiso 1 1 calc R U . . .
H8BB H 0.5442 0.3499 1.5393 0.029 Uiso 1 1 calc R U . . .
H8BC H 0.7128 0.2938 1.6016 0.029 Uiso 1 1 calc R U . . .
C9B C 0.8741(14) 0.3680(5) 1.3685(16) 0.020(2) Uani 1 1 d . . . . .
H9BA H 0.9235 0.3809 1.2482 0.030 Uiso 1 1 calc R U . . .
H9BB H 0.9817 0.3437 1.4601 0.030 Uiso 1 1 calc R U . . .
H9BC H 0.8383 0.4072 1.4366 0.030 Uiso 1 1 calc R U . . .
C10B C 0.1894(16) 0.3567(7) 0.8959(19) 0.030(3) Uani 1 1 d . . . . .
H10D H 0.0525 0.3370 0.8693 0.046 Uiso 1 1 calc R U . . .
H10E H 0.2559 0.3468 0.7840 0.046 Uiso 1 1 calc R U . . .
H10F H 0.1779 0.4043 0.9092 0.046 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
S1A C3A 1.718(10) . ?
N1A N2A 1.434(11) . ?
N1A C7A 1.455(13) . ?
N1A H1A 0.88(4) . ?
N2A C3A 1.333(12) . ?
N2A H2A 0.88(4) . ?
N4A C3A 1.322(11) . ?
N4A C5A 1.518(12) . ?
N4A H4A 0.89(4) . ?
C5A C9A 1.510(15) . ?
C5A C8A 1.528(13) . ?
C5A C6A 1.566(14) . ?
C6A C7A 1.515(14) . ?
C6A H6AA 0.9900 . ?
C6A H6AB 0.9900 . ?
C7A C10A 1.528(15) . ?
C7A H7AA 1.0000 . ?
C8A H8AA 0.9800 . ?
C8A H8AB 0.9800 . ?
C8A H8AC 0.9800 . ?
C9A H9AA 0.9800 . ?
C9A H9AB 0.9800 . ?
C9A H9AC 0.9800 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
S1B C3B 1.715(10) . ?
N1B N2B 1.415(11) . ?
N1B C7B 1.452(15) . ?
N1B H1B 0.89(4) . ?
N2B C3B 1.336(11) . ?
N2B H2B 0.88(4) . ?
N4B C3B 1.355(12) . ?
N4B C5B 1.483(14) . ?
N4B H4B 0.89(4) . ?
C5B C6B 1.504(13) . ?
C5B C8B 1.524(14) . ?
C5B C9B 1.544(13) . ?
C6B C7B 1.549(14) . ?
C6B H6BA 0.9900 . ?
C6B H6BB 0.9900 . ?
C7B C10B 1.504(15) . ?
C7B H7BA 1.0000 . ?
C8B H8BA 0.9800 . ?
C8B H8BB 0.9800 . ?
C8B H8BC 0.9800 . ?
C9B H9BA 0.9800 . ?
C9B H9BB 0.9800 . ?
C9B H9BC 0.9800 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 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
N2A N1A C7A 113.0(8) . . ?
N2A N1A H1A 105(7) . . ?
C7A N1A H1A 125(6) . . ?
C3A N2A N1A 120.4(7) . . ?
C3A N2A H2A 134(7) . . ?
N1A N2A H2A 105(7) . . ?
C3A N4A C5A 129.6(8) . . ?
C3A N4A H4A 113(7) . . ?
C5A N4A H4A 117(7) . . ?
N4A C3A N2A 119.9(9) . . ?
N4A C3A S1A 121.3(7) . . ?
N2A C3A S1A 118.8(7) . . ?
C9A C5A N4A 104.1(8) . . ?
C9A C5A C8A 111.5(8) . . ?
N4A C5A C8A 111.0(8) . . ?
C9A C5A C6A 108.1(8) . . ?
N4A C5A C6A 109.3(7) . . ?
C8A C5A C6A 112.5(9) . . ?
C7A C6A C5A 116.2(9) . . ?
C7A C6A H6AA 108.2 . . ?
C5A C6A H6AA 108.2 . . ?
C7A C6A H6AB 108.2 . . ?
C5A C6A H6AB 108.2 . . ?
H6AA C6A H6AB 107.4 . . ?
N1A C7A C6A 108.0(8) . . ?
N1A C7A C10A 114.9(8) . . ?
C6A C7A C10A 110.1(9) . . ?
N1A C7A H7AA 107.9 . . ?
C6A C7A H7AA 107.9 . . ?
C10A C7A H7AA 107.9 . . ?
C5A C8A H8AA 109.5 . . ?
C5A C8A H8AB 109.5 . . ?
H8AA C8A H8AB 109.5 . . ?
C5A C8A H8AC 109.5 . . ?
H8AA C8A H8AC 109.5 . . ?
H8AB C8A H8AC 109.5 . . ?
C5A C9A H9AA 109.5 . . ?
C5A C9A H9AB 109.5 . . ?
H9AA C9A H9AB 109.5 . . ?
C5A C9A H9AC 109.5 . . ?
H9AA C9A H9AC 109.5 . . ?
H9AB C9A H9AC 109.5 . . ?
C7A C10A H10A 109.5 . . ?
C7A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C7A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
N2B N1B C7B 111.1(8) . . ?
N2B N1B H1B 106(7) . . ?
C7B N1B H1B 100(6) . . ?
C3B N2B N1B 119.5(7) . . ?
C3B N2B H2B 115(7) . . ?
N1B N2B H2B 124(7) . . ?
C3B N4B C5B 130.2(8) . . ?
C3B N4B H4B 121(7) . . ?
C5B N4B H4B 106(7) . . ?
N2B C3B N4B 118.4(9) . . ?
N2B C3B S1B 120.3(7) . . ?
N4B C3B S1B 121.1(7) . . ?
N4B C5B C6B 110.4(7) . . ?
N4B C5B C8B 110.5(8) . . ?
C6B C5B C8B 112.7(8) . . ?
N4B C5B C9B 107.2(8) . . ?
C6B C5B C9B 108.1(8) . . ?
C8B C5B C9B 107.8(8) . . ?
C5B C6B C7B 116.4(9) . . ?
C5B C6B H6BA 108.2 . . ?
C7B C6B H6BA 108.2 . . ?
C5B C6B H6BB 108.2 . . ?
C7B C6B H6BB 108.2 . . ?
H6BA C6B H6BB 107.3 . . ?
N1B C7B C10B 115.7(10) . . ?
N1B C7B C6B 107.9(9) . . ?
C10B C7B C6B 113.1(10) . . ?
N1B C7B H7BA 106.5 . . ?
C10B C7B H7BA 106.5 . . ?
C6B C7B H7BA 106.5 . . ?
C5B C8B H8BA 109.5 . . ?
C5B C8B H8BB 109.5 . . ?
H8BA C8B H8BB 109.5 . . ?
C5B C8B H8BC 109.5 . . ?
H8BA C8B H8BC 109.5 . . ?
H8BB C8B H8BC 109.5 . . ?
C5B C9B H9BA 109.5 . . ?
C5B C9B H9BB 109.5 . . ?
H9BA C9B H9BB 109.5 . . ?
C5B C9B H9BC 109.5 . . ?
H9BA C9B H9BC 109.5 . . ?
H9BB C9B H9BC 109.5 . . ?
C7B C10B H10D 109.5 . . ?
C7B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C7B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 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
C7A N1A N2A C3A -88.4(10) . . . . ?
C5A N4A C3A N2A 28.8(15) . . . . ?
C5A N4A C3A S1A -152.2(8) . . . . ?
N1A N2A C3A N4A 16.0(14) . . . . ?
N1A N2A C3A S1A -163.0(7) . . . . ?
C3A N4A C5A C9A 128.7(10) . . . . ?
C3A N4A C5A C8A -111.2(11) . . . . ?
C3A N4A C5A C6A 13.4(13) . . . . ?
C9A C5A C6A C7A 173.5(8) . . . . ?
N4A C5A C6A C7A -73.7(11) . . . . ?
C8A C5A C6A C7A 50.0(12) . . . . ?
N2A N1A C7A C6A 53.1(10) . . . . ?
N2A N1A C7A C10A -70.2(11) . . . . ?
C5A C6A C7A N1A 37.4(12) . . . . ?
C5A C6A C7A C10A 163.5(8) . . . . ?
C7B N1B N2B C3B 92.2(11) . . . . ?
N1B N2B C3B N4B -21.1(14) . . . . ?
N1B N2B C3B S1B 162.9(7) . . . . ?
C5B N4B C3B N2B -27.1(15) . . . . ?
C5B N4B C3B S1B 148.9(8) . . . . ?
C3B N4B C5B C6B -13.2(14) . . . . ?
C3B N4B C5B C8B 112.1(11) . . . . ?
C3B N4B C5B C9B -130.7(10) . . . . ?
N4B C5B C6B C7B 72.3(11) . . . . ?
C8B C5B C6B C7B -51.7(12) . . . . ?
C9B C5B C6B C7B -170.7(8) . . . . ?
N2B N1B C7B C10B 72.6(11) . . . . ?
N2B N1B C7B C6B -55.1(10) . . . . ?
C5B C6B C7B N1B -36.4(12) . . . . ?
C5B C6B C7B C10B -165.6(10) . . . . ?

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
N1A H1A S1A 0.88(4) 2.83(5) 3.653(9) 156(8) 1_655
N2A H2A S1B 0.88(4) 2.50(5) 3.344(8) 161(10) .
N4A H4A S1B 0.89(4) 2.60(4) 3.487(8) 175(9) 1_454
N1B H1B S1B 0.89(4) 2.83(5) 3.688(8) 164(8) 1_455
N2B H2B S1A 0.88(4) 2.56(6) 3.360(8) 152(9) .
N4B H4B S1A 0.89(4) 2.68(6) 3.463(8) 148(8) 1_656

_refine_diff_density_max         1.387
_refine_diff_density_min         -1.721
_refine_diff_density_rms         0.134

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_No_11_LT
_database_code_depnum_ccdc_archive 'CCDC 1578759'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 N3 S'
_chemical_formula_weight         213.34

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           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                   22.7327(10)
_cell_length_b                   9.7061(4)
_cell_length_c                   10.6589(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.340(3)
_cell_angle_gamma                90
_cell_volume                     2268.05(16)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5378
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      34.62

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.24
_exptl_absorpt_coefficient_mu    0.253
_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   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20768
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.199
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4986
_reflns_number_gt                3779
_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 (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)+(0.0434P)²+0.4875P] 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         4986
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0935
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.44194(2) 0.83177(2) 0.37747(2) 0.01301(6) Uani 1 1 d . . . . .
N1 N 0.56632(4) 0.82792(8) 0.71149(7) 0.01162(14) Uani 1 1 d . . . . .
H1 H 0.5766(6) 0.9103(14) 0.6900(12) 0.019(3) Uiso 1 1 d . . . . .
N2 N 0.51425(4) 0.78737(9) 0.61135(7) 0.01307(15) Uani 1 1 d . . . . .
H2 H 0.4805(7) 0.8090(14) 0.6328(14) 0.027(4) Uiso 1 1 d . . . . .
N4 N 0.56042(4) 0.77017(8) 0.44070(7) 0.01225(15) Uani 1 1 d . . . . .
H4 H 0.5551(7) 0.7837(15) 0.3581(14) 0.028(4) Uiso 1 1 d . . . . .
C3 C 0.51061(4) 0.79592(9) 0.48223(8) 0.01054(15) Uani 1 1 d . . . . .
C5 C 0.61018(4) 0.67140(9) 0.49950(8) 0.01138(15) Uani 1 1 d . . . . .
C6 C 0.65113(4) 0.72246(9) 0.63079(8) 0.01159(16) Uani 1 1 d . . . . .
H6A H 0.6838 0.6515 0.6597 0.014 Uiso 1 1 calc R U . . .
C7 C 0.61764(4) 0.73074(10) 0.73877(8) 0.01234(16) Uani 1 1 d . . . . .
H7A H 0.6015 0.6370 0.7500 0.015 Uiso 1 1 calc R U . . .
C8 C 0.66198(5) 0.77312(12) 0.86825(9) 0.01859(19) Uani 1 1 d . . . . .
H8A H 0.6392 0.7825 0.9351 0.022 Uiso 1 1 calc R U . . .
H8B H 0.6928 0.6997 0.8969 0.022 Uiso 1 1 calc R U . . .
C9 C 0.69427(5) 0.90846(12) 0.85782(10) 0.0227(2) Uani 1 1 d . . . . .
H9A H 0.7241 0.9289 0.9419 0.027 Uiso 1 1 calc R U . . .
H9B H 0.6640 0.9842 0.8385 0.027 Uiso 1 1 calc R U . . .
C10 C 0.72732(5) 0.90025(13) 0.75049(11) 0.0252(2) Uani 1 1 d . . . . .
H10A H 0.7455 0.9910 0.7410 0.030 Uiso 1 1 calc R U . . .
H10B H 0.7608 0.8321 0.7752 0.030 Uiso 1 1 calc R U . . .
C11 C 0.68386(5) 0.85846(10) 0.62067(10) 0.01641(18) Uani 1 1 d . . . . .
H11A H 0.7072 0.8488 0.5547 0.020 Uiso 1 1 calc R U . . .
H11B H 0.6532 0.9320 0.5912 0.020 Uiso 1 1 calc R U . . .
C12 C 0.64798(5) 0.65582(10) 0.40037(9) 0.01637(18) Uani 1 1 d . . . . .
H12A H 0.6816 0.5914 0.4343 0.025 Uiso 1 1 calc R U . . .
H12B H 0.6220 0.6203 0.3183 0.025 Uiso 1 1 calc R U . . .
H12C H 0.6645 0.7457 0.3853 0.025 Uiso 1 1 calc R U . . .
C13 C 0.58272(5) 0.52991(10) 0.51429(10) 0.01753(19) Uani 1 1 d . . . . .
H13A H 0.6155 0.4650 0.5530 0.026 Uiso 1 1 calc R U . . .
H13B H 0.5552 0.5382 0.5707 0.026 Uiso 1 1 calc R U . . .
H13C H 0.5599 0.4961 0.4286 0.026 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 C3 1.6977(9) . ?
N1 N2 1.4238(11) . ?
N1 C7 1.4682(12) . ?
N1 H1 0.880(14) . ?
N2 C3 1.3592(11) . ?
N2 H2 0.882(15) . ?
N4 C3 1.3438(11) . ?
N4 C5 1.4887(12) . ?
N4 H4 0.866(14) . ?
C5 C13 1.5338(13) . ?
C5 C12 1.5357(12) . ?
C5 C6 1.5432(13) . ?
C6 C11 1.5330(13) . ?
C6 C7 1.5409(12) . ?
C6 H6A 1.0000 . ?
C7 C8 1.5342(13) . ?
C7 H7A 1.0000 . ?
C8 C9 1.5232(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.5279(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.5272(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
N2 N1 C7 115.49(7) . . ?
N2 N1 H1 106.3(9) . . ?
C7 N1 H1 112.6(8) . . ?
C3 N2 N1 123.92(7) . . ?
C3 N2 H2 115.1(9) . . ?
N1 N2 H2 110.3(9) . . ?
C3 N4 C5 126.42(7) . . ?
C3 N4 H4 113.8(10) . . ?
C5 N4 H4 114.3(10) . . ?
N4 C3 N2 119.43(8) . . ?
N4 C3 S1 121.98(7) . . ?
N2 C3 S1 118.53(6) . . ?
N4 C5 C13 109.59(8) . . ?
N4 C5 C12 105.96(7) . . ?
C13 C5 C12 107.43(7) . . ?
N4 C5 C6 112.58(7) . . ?
C13 C5 C6 111.01(7) . . ?
C12 C5 C6 110.03(7) . . ?
C11 C6 C7 110.64(7) . . ?
C11 C6 C5 113.60(7) . . ?
C7 C6 C5 113.29(7) . . ?
C11 C6 H6A 106.2 . . ?
C7 C6 H6A 106.2 . . ?
C5 C6 H6A 106.2 . . ?
N1 C7 C8 107.72(8) . . ?
N1 C7 C6 114.16(7) . . ?
C8 C7 C6 110.43(8) . . ?
N1 C7 H7A 108.1 . . ?
C8 C7 H7A 108.1 . . ?
C6 C7 H7A 108.1 . . ?
C9 C8 C7 112.35(8) . . ?
C9 C8 H8A 109.1 . . ?
C7 C8 H8A 109.1 . . ?
C9 C8 H8B 109.1 . . ?
C7 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C10 110.59(9) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 111.33(9) . . ?
C11 C10 H10A 109.4 . . ?
C9 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C9 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
C10 C11 C6 112.00(8) . . ?
C10 C11 H11A 109.2 . . ?
C6 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C6 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C7 N1 N2 C3 -77.03(11) . . . . ?
C5 N4 C3 N2 32.18(13) . . . . ?
C5 N4 C3 S1 -144.90(8) . . . . ?
N1 N2 C3 N4 36.40(13) . . . . ?
N1 N2 C3 S1 -146.42(8) . . . . ?
C3 N4 C5 C13 51.91(12) . . . . ?
C3 N4 C5 C12 167.53(9) . . . . ?
C3 N4 C5 C6 -72.16(11) . . . . ?
N4 C5 C6 C11 -61.10(10) . . . . ?
C13 C5 C6 C11 175.62(7) . . . . ?
C12 C5 C6 C11 56.83(10) . . . . ?
N4 C5 C6 C7 66.26(9) . . . . ?
C13 C5 C6 C7 -57.02(10) . . . . ?
C12 C5 C6 C7 -175.80(7) . . . . ?
N2 N1 C7 C8 -166.37(7) . . . . ?
N2 N1 C7 C6 70.62(10) . . . . ?
C11 C6 C7 N1 66.79(10) . . . . ?
C5 C6 C7 N1 -62.10(10) . . . . ?
C11 C6 C7 C8 -54.74(10) . . . . ?
C5 C6 C7 C8 176.36(8) . . . . ?
N1 C7 C8 C9 -69.31(10) . . . . ?
C6 C7 C8 C9 55.96(11) . . . . ?
C7 C8 C9 C10 -55.93(12) . . . . ?
C8 C9 C10 C11 55.04(13) . . . . ?
C9 C10 C11 C6 -55.59(12) . . . . ?
C7 C6 C11 C10 55.33(11) . . . . ?
C5 C6 C11 C10 -175.95(8) . . . . ?

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 S1 0.880(14) 2.608(14) 3.4279(9) 155.4(11) 5_676
N2 H2 N1 0.882(15) 2.204(15) 2.9842(11) 147.4(13) 2_656
N4 H4 S1 0.866(14) 2.572(14) 3.4300(8) 170.7(13) 2_655

_refine_diff_density_max         0.465
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_No_10_LT_twin
_database_code_depnum_ccdc_archive 'CCDC 1578758'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H19 N3 S'
_chemical_formula_weight         225.35

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                   8.6412(18)
_cell_length_b                   10.610(2)
_cell_length_c                   12.608(3)
_cell_angle_alpha                90
_cell_angle_beta                 106.492(9)
_cell_angle_gamma                90
_cell_volume                     1108.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1710
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      25.74

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6397
_diffrn_reflns_av_unetI/netI     0.1302
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.195
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             6397
_reflns_number_gt                3840
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1248P)²+0.4592P] 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         6397
_refine_ls_number_parameters     149
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1555
_refine_ls_R_factor_gt           0.0910
_refine_ls_wR_factor_ref         0.2590
_refine_ls_wR_factor_gt          0.2269
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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 0.26309(14) 0.53615(14) 0.51797(12) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.0191(5) 0.2410(4) 0.3620(4) 0.0193(10) Uani 1 1 d . . . . .
H1 H 0.093(8) 0.177(6) 0.402(5) 0.044(19) Uiso 1 1 d . . . . .
N2 N 0.0712(5) 0.3596(5) 0.4094(4) 0.0226(11) Uani 1 1 d . . . . .
H2 H 0.007(8) 0.398(7) 0.439(6) 0.05(2) Uiso 1 1 d . . . . .
N4 N 0.3334(5) 0.3595(4) 0.3902(4) 0.0201(10) Uani 1 1 d . . . . .
H4 H 0.422(8) 0.399(6) 0.415(5) 0.038(18) Uiso 1 1 d . . . . .
C3 C 0.2216(6) 0.4084(5) 0.4330(4) 0.0195(11) Uani 1 1 d . . . . .
C5 C 0.3217(5) 0.2611(5) 0.3043(4) 0.0181(11) Uani 1 1 d . . . . .
C6 C 0.1626(5) 0.2673(5) 0.2125(4) 0.0181(11) Uani 1 1 d . . . . .
H6A H 0.1716 0.2042 0.1557 0.022 Uiso 1 1 calc R U . . .
C7 C 0.0081(5) 0.2326(5) 0.2449(4) 0.0180(11) Uani 1 1 d . . . . .
H7A H -0.0221 0.1441 0.2202 0.022 Uiso 1 1 calc R U . . .
C8 C 0.3570(6) 0.1296(5) 0.3584(5) 0.0255(12) Uani 1 1 d . . . . .
H8A H 0.3112 0.1222 0.4217 0.031 Uiso 1 1 calc R U . . .
H8B H 0.3105 0.0625 0.3042 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5393(6) 0.1198(5) 0.3969(5) 0.0255(13) Uani 1 1 d . . . . .
H9A H 0.5746 0.0309 0.4096 0.031 Uiso 1 1 calc R U . . .
H9B H 0.5846 0.1684 0.4658 0.031 Uiso 1 1 calc R U . . .
C10 C 0.5890(7) 0.1765(6) 0.3009(5) 0.0329(14) Uani 1 1 d . . . . .
H10A H 0.5849 0.1122 0.2433 0.039 Uiso 1 1 calc R U . . .
H10B H 0.7000 0.2108 0.3265 0.039 Uiso 1 1 calc R U . . .
C11 C 0.4675(5) 0.2815(5) 0.2561(4) 0.0197(11) Uani 1 1 d . . . . .
H11A H 0.4307 0.2784 0.1743 0.024 Uiso 1 1 calc R U . . .
H11B H 0.5177 0.3648 0.2789 0.024 Uiso 1 1 calc R U . . .
C12 C 0.1243(6) 0.3930(5) 0.1521(4) 0.0206(11) Uani 1 1 d . . . . .
H12A H 0.1882 0.4043 0.0989 0.025 Uiso 1 1 calc R U . . .
H12B H 0.1461 0.4644 0.2049 0.025 Uiso 1 1 calc R U . . .
C13 C -0.0558(6) 0.3824(5) 0.0924(4) 0.0223(12) Uani 1 1 d . . . . .
H13A H -0.1043 0.4665 0.0713 0.027 Uiso 1 1 calc R U . . .
H13B H -0.0745 0.3296 0.0251 0.027 Uiso 1 1 calc R U . . .
C14 C -0.1250(6) 0.3203(5) 0.1777(4) 0.0214(12) Uani 1 1 d . . . . .
H14A H -0.2234 0.2716 0.1409 0.026 Uiso 1 1 calc R U . . .
H14B H -0.1529 0.3845 0.2262 0.026 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 C3 1.702(6) . ?
N1 N2 1.411(6) . ?
N1 C7 1.455(7) . ?
N1 H1 0.97(7) . ?
N2 C3 1.351(6) . ?
N2 H2 0.86(7) . ?
N4 C3 1.338(6) . ?
N4 C5 1.486(7) . ?
N4 H4 0.85(7) . ?
C5 C6 1.526(7) . ?
C5 C8 1.545(7) . ?
C5 C11 1.561(6) . ?
C6 C12 1.525(7) . ?
C6 C7 1.548(6) . ?
C6 H6A 1.0000 . ?
C7 C14 1.534(7) . ?
C7 H7A 1.0000 . ?
C8 C9 1.514(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(8) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.526(7) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.529(7) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.521(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?

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
N2 N1 C7 113.9(4) . . ?
N2 N1 H1 108(4) . . ?
C7 N1 H1 109(4) . . ?
C3 N2 N1 127.3(4) . . ?
C3 N2 H2 115(5) . . ?
N1 N2 H2 116(5) . . ?
C3 N4 C5 131.2(4) . . ?
C3 N4 H4 110(4) . . ?
C5 N4 H4 119(4) . . ?
N4 C3 N2 121.5(5) . . ?
N4 C3 S1 121.1(4) . . ?
N2 C3 S1 117.5(4) . . ?
N4 C5 C6 112.5(4) . . ?
N4 C5 C8 110.4(4) . . ?
C6 C5 C8 113.3(4) . . ?
N4 C5 C11 106.9(4) . . ?
C6 C5 C11 110.6(4) . . ?
C8 C5 C11 102.5(4) . . ?
C12 C6 C5 115.9(4) . . ?
C12 C6 C7 105.0(4) . . ?
C5 C6 C7 116.7(4) . . ?
C12 C6 H6A 106.1 . . ?
C5 C6 H6A 106.1 . . ?
C7 C6 H6A 106.1 . . ?
N1 C7 C14 110.3(4) . . ?
N1 C7 C6 116.1(4) . . ?
C14 C7 C6 106.1(4) . . ?
N1 C7 H7A 108.0 . . ?
C14 C7 H7A 108.0 . . ?
C6 C7 H7A 108.0 . . ?
C9 C8 C5 105.1(4) . . ?
C9 C8 H8A 110.7 . . ?
C5 C8 H8A 110.7 . . ?
C9 C8 H8B 110.7 . . ?
C5 C8 H8B 110.7 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 C10 102.8(4) . . ?
C8 C9 H9A 111.2 . . ?
C10 C9 H9A 111.2 . . ?
C8 C9 H9B 111.2 . . ?
C10 C9 H9B 111.2 . . ?
H9A C9 H9B 109.1 . . ?
C9 C10 C11 105.3(4) . . ?
C9 C10 H10A 110.7 . . ?
C11 C10 H10A 110.7 . . ?
C9 C10 H10B 110.7 . . ?
C11 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C10 C11 C5 107.5(4) . . ?
C10 C11 H11A 110.2 . . ?
C5 C11 H11A 110.2 . . ?
C10 C11 H11B 110.2 . . ?
C5 C11 H11B 110.2 . . ?
H11A C11 H11B 108.5 . . ?
C6 C12 C13 103.2(4) . . ?
C6 C12 H12A 111.1 . . ?
C13 C12 H12A 111.1 . . ?
C6 C12 H12B 111.1 . . ?
C13 C12 H12B 111.1 . . ?
H12A C12 H12B 109.1 . . ?
C14 C13 C12 103.5(4) . . ?
C14 C13 H13A 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C14 C13 H13B 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.0 . . ?
C13 C14 C7 105.7(4) . . ?
C13 C14 H14A 110.6 . . ?
C7 C14 H14A 110.6 . . ?
C13 C14 H14B 110.6 . . ?
C7 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?

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
C7 N1 N2 C3 -72.6(6) . . . . ?
C5 N4 C3 N2 8.1(8) . . . . ?
C5 N4 C3 S1 -171.0(4) . . . . ?
N1 N2 C3 N4 15.6(8) . . . . ?
N1 N2 C3 S1 -165.2(4) . . . . ?
C3 N4 C5 C6 36.2(7) . . . . ?
C3 N4 C5 C8 -91.4(6) . . . . ?
C3 N4 C5 C11 157.8(5) . . . . ?
N4 C5 C6 C12 56.6(6) . . . . ?
C8 C5 C6 C12 -177.3(4) . . . . ?
C11 C5 C6 C12 -62.8(6) . . . . ?
N4 C5 C6 C7 -67.8(6) . . . . ?
C8 C5 C6 C7 58.2(6) . . . . ?
C11 C5 C6 C7 172.7(4) . . . . ?
N2 N1 C7 C14 -66.1(5) . . . . ?
N2 N1 C7 C6 54.7(6) . . . . ?
C12 C6 C7 N1 -109.0(5) . . . . ?
C5 C6 C7 N1 20.9(7) . . . . ?
C12 C6 C7 C14 14.0(5) . . . . ?
C5 C6 C7 C14 143.8(5) . . . . ?
N4 C5 C8 C9 -82.0(5) . . . . ?
C6 C5 C8 C9 150.8(4) . . . . ?
C11 C5 C8 C9 31.6(5) . . . . ?
C5 C8 C9 C10 -41.8(6) . . . . ?
C8 C9 C10 C11 34.9(6) . . . . ?
C9 C10 C11 C5 -15.4(6) . . . . ?
N4 C5 C11 C10 106.4(5) . . . . ?
C6 C5 C11 C10 -130.8(5) . . . . ?
C8 C5 C11 C10 -9.7(6) . . . . ?
C5 C6 C12 C13 -164.2(4) . . . . ?
C7 C6 C12 C13 -33.9(5) . . . . ?
C6 C12 C13 C14 41.2(5) . . . . ?
C12 C13 C14 C7 -32.5(5) . . . . ?
N1 C7 C14 C13 138.1(4) . . . . ?
C6 C7 C14 C13 11.5(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
N2 H2 S1 0.86(7) 2.64(7) 3.451(5) 160(6) 3_566
N4 H4 S1 0.85(7) 2.70(7) 3.526(4) 164(6) 3_666

_refine_diff_density_max         0.648
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.112

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_No_12_LT
_database_code_depnum_ccdc_archive 'CCDC 1578757'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H17 N3 S'
_chemical_formula_weight         199.31

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                   5.6776(5)
_cell_length_b                   8.9813(9)
_cell_length_c                   20.467(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.743(5)
_cell_angle_gamma                90
_cell_volume                     1043.18(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1789
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      26.99

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.270
_shelx_estimated_absorpt_T_min   0.877
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9387
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_av_R_equivalents  0.0650
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         4.248
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2381
_reflns_number_gt                1730
_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 (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)+(0.0391P)²+0.5416P] 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         2381
_refine_ls_number_parameters     131
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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 0.98964(10) 0.28394(6) 0.53741(3) 0.01798(16) Uani 1 1 d . . . . .
N4 N 0.7068(3) 0.3918(2) 0.44280(9) 0.0148(4) Uani 1 1 d . . . . .
H4 H 0.812(4) 0.464(3) 0.4464(12) 0.028(7) Uiso 1 1 d . . . . .
N1 N 0.4215(4) 0.1231(2) 0.44445(9) 0.0151(4) Uani 1 1 d . . . . .
H1 H 0.291(4) 0.162(3) 0.4506(12) 0.020(7) Uiso 1 1 d . . . . .
N2 N 0.5927(3) 0.1700(2) 0.49243(9) 0.0160(4) Uani 1 1 d . . . . .
H2 H 0.627(4) 0.104(3) 0.5166(12) 0.024(7) Uiso 1 1 d . . . . .
C3 C 0.7442(4) 0.2834(2) 0.48695(10) 0.0146(4) Uani 1 1 d . . . . .
C5 C 0.4893(4) 0.4226(2) 0.40339(10) 0.0146(4) Uani 1 1 d . . . . .
H5A H 0.3547 0.4289 0.4337 0.017 Uiso 1 1 calc R U . . .
C6 C 0.4318(4) 0.3024(2) 0.35207(10) 0.0150(4) Uani 1 1 d . . . . .
H6A H 0.5236 0.3243 0.3123 0.018 Uiso 1 1 calc R U . . .
C7 C 0.5029(4) 0.1467(2) 0.37722(10) 0.0154(5) Uani 1 1 d . . . . .
H7A H 0.6790 0.1419 0.3789 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1687(4) 0.3096(2) 0.33315(11) 0.0181(5) Uani 1 1 d . . . . .
H8A H 0.0763 0.3032 0.3733 0.022 Uiso 1 1 calc R U . . .
H8B H 0.1341 0.4070 0.3123 0.022 Uiso 1 1 calc R U . . .
C9 C 0.0895(4) 0.1852(2) 0.28633(11) 0.0204(5) Uani 1 1 d . . . . .
H9A H -0.0827 0.1920 0.2778 0.024 Uiso 1 1 calc R U . . .
H9B H 0.1687 0.1969 0.2442 0.024 Uiso 1 1 calc R U . . .
C10 C 0.1503(4) 0.0330(2) 0.31579(12) 0.0240(5) Uani 1 1 d . . . . .
H10A H 0.0613 0.0181 0.3561 0.029 Uiso 1 1 calc R U . . .
H10B H 0.1038 -0.0463 0.2844 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4138(4) 0.0223(2) 0.33178(11) 0.0210(5) Uani 1 1 d . . . . .
H11A H 0.5007 0.0265 0.2906 0.025 Uiso 1 1 calc R U . . .
H11B H 0.4478 -0.0750 0.3527 0.025 Uiso 1 1 calc R U . . .
C12 C 0.5207(4) 0.5748(2) 0.37171(11) 0.0199(5) Uani 1 1 d . . . . .
H12A H 0.3801 0.5990 0.3449 0.030 Uiso 1 1 calc R U . . .
H12B H 0.6587 0.5726 0.3441 0.030 Uiso 1 1 calc R U . . .
H12C H 0.5436 0.6505 0.4058 0.030 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 C3 1.709(2) . ?
N4 C3 1.341(3) . ?
N4 C5 1.480(3) . ?
N4 H4 0.88(3) . ?
N1 N2 1.425(3) . ?
N1 C7 1.480(3) . ?
N1 H1 0.83(3) . ?
N2 C3 1.340(3) . ?
N2 H2 0.79(3) . ?
C5 C12 1.526(3) . ?
C5 C6 1.534(3) . ?
C5 H5A 1.0000 . ?
C6 C8 1.533(3) . ?
C6 C7 1.540(3) . ?
C6 H6A 1.0000 . ?
C7 C11 1.529(3) . ?
C7 H7A 1.0000 . ?
C8 C9 1.530(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.529(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C3 N4 C5 127.96(18) . . ?
C3 N4 H4 112.5(17) . . ?
C5 N4 H4 117.5(17) . . ?
N2 N1 C7 111.86(17) . . ?
N2 N1 H1 111.5(17) . . ?
C7 N1 H1 112.7(17) . . ?
C3 N2 N1 126.42(18) . . ?
C3 N2 H2 118.3(19) . . ?
N1 N2 H2 111.1(19) . . ?
N2 C3 N4 121.3(2) . . ?
N2 C3 S1 117.73(17) . . ?
N4 C3 S1 120.98(16) . . ?
N4 C5 C12 106.99(17) . . ?
N4 C5 C6 113.46(17) . . ?
C12 C5 C6 111.39(17) . . ?
N4 C5 H5A 108.3 . . ?
C12 C5 H5A 108.3 . . ?
C6 C5 H5A 108.3 . . ?
C8 C6 C5 109.17(17) . . ?
C8 C6 C7 111.49(17) . . ?
C5 C6 C7 111.23(17) . . ?
C8 C6 H6A 108.3 . . ?
C5 C6 H6A 108.3 . . ?
C7 C6 H6A 108.3 . . ?
N1 C7 C11 110.71(17) . . ?
N1 C7 C6 110.78(17) . . ?
C11 C7 C6 112.41(18) . . ?
N1 C7 H7A 107.6 . . ?
C11 C7 H7A 107.6 . . ?
C6 C7 H7A 107.6 . . ?
C9 C8 C6 113.12(17) . . ?
C9 C8 H8A 109.0 . . ?
C6 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C6 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 110.30(18) . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C8 C9 H9B 109.6 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 110.44(19) . . ?
C11 C10 H10A 109.6 . . ?
C9 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
C9 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C10 C11 C7 112.89(18) . . ?
C10 C11 H11A 109.0 . . ?
C7 C11 H11A 109.0 . . ?
C10 C11 H11B 109.0 . . ?
C7 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C5 C12 H12A 109.5 . . ?
C5 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C5 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
C7 N1 N2 C3 32.8(3) . . . . ?
N1 N2 C3 N4 19.4(3) . . . . ?
N1 N2 C3 S1 -159.68(17) . . . . ?
C5 N4 C3 N2 12.0(3) . . . . ?
C5 N4 C3 S1 -168.96(16) . . . . ?
C3 N4 C5 C12 168.6(2) . . . . ?
C3 N4 C5 C6 -68.2(3) . . . . ?
N4 C5 C6 C8 158.30(17) . . . . ?
C12 C5 C6 C8 -80.9(2) . . . . ?
N4 C5 C6 C7 34.9(2) . . . . ?
C12 C5 C6 C7 155.66(18) . . . . ?
N2 N1 C7 C11 144.87(18) . . . . ?
N2 N1 C7 C6 -89.7(2) . . . . ?
C8 C6 C7 N1 -75.4(2) . . . . ?
C5 C6 C7 N1 46.7(2) . . . . ?
C8 C6 C7 C11 49.0(2) . . . . ?
C5 C6 C7 C11 171.11(18) . . . . ?
C5 C6 C8 C9 -175.16(17) . . . . ?
C7 C6 C8 C9 -51.9(2) . . . . ?
C6 C8 C9 C10 56.2(2) . . . . ?
C8 C9 C10 C11 -57.1(2) . . . . ?
C9 C10 C11 C7 56.1(3) . . . . ?
N1 C7 C11 C10 72.3(2) . . . . ?
C6 C7 C11 C10 -52.1(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
N4 H4 S1 0.88(3) 2.55(3) 3.4017(19) 163(2) 3_766
N1 H1 S1 0.83(3) 2.73(3) 3.464(2) 148(2) 1_455
N2 H2 N1 0.79(3) 2.21(3) 2.934(3) 152(2) 3_656

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.069

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_No_14_LT
_database_code_depnum_ccdc_archive 'CCDC 1578760'
_audit_update_record             
;
2018-01-24 deposited with the CCDC.
2018-10-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C7 H15 N3 O'
_chemical_formula_weight         157.22

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'

_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'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   7.2701(8)
_cell_length_b                   12.9061(11)
_cell_length_c                   18.374(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1724.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5874
_cell_measurement_theta_min      3.16
_cell_measurement_theta_max      29.86

_exptl_crystal_description       fragment
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.420
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16972
_diffrn_reflns_av_unetI/netI     0.0403
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.366
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             2494
_reflns_number_gt                1839
_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 (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)+(0.0497P)²+1.7163P] 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         2494
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0826
_refine_ls_R_factor_gt           0.0560
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1296
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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
O1 O 0.54551(16) 0.75723(10) 0.49467(7) 0.0195(3) Uani 1 1 d . . . . .
N1 N 0.72912(19) 0.52678(11) 0.56955(8) 0.0169(3) Uani 1 1 d . . . . .
H1 H 0.674(3) 0.4897(18) 0.5338(13) 0.027(6) Uiso 1 1 d . . . . .
N2 N 0.70630(19) 0.63325(11) 0.55325(8) 0.0166(3) Uani 1 1 d . . . . .
H2 H 0.805(3) 0.6634(18) 0.5349(13) 0.031(6) Uiso 1 1 d . . . . .
N4 N 0.38368(19) 0.63404(11) 0.55629(8) 0.0151(3) Uani 1 1 d . . . . .
H4 H 0.290(3) 0.6730(17) 0.5405(12) 0.022(5) Uiso 1 1 d . . . . .
C3 C 0.5450(2) 0.67870(12) 0.53329(9) 0.0145(3) Uani 1 1 d . . . . .
C5 C 0.3506(2) 0.59616(13) 0.63170(9) 0.0163(3) Uani 1 1 d . . . . .
C6 C 0.4507(2) 0.49422(13) 0.64631(9) 0.0171(3) Uani 1 1 d . . . . .
H6A H 0.4035 0.4419 0.6116 0.020 Uiso 1 1 calc R U . . .
H6B H 0.4172 0.4706 0.6958 0.020 Uiso 1 1 calc R U . . .
C7 C 0.6604(2) 0.49523(13) 0.64084(9) 0.0166(3) Uani 1 1 d . . . . .
H7A H 0.7096 0.5443 0.6782 0.020 Uiso 1 1 calc R U . . .
C8 C 0.4028(3) 0.68067(14) 0.68658(10) 0.0203(3) Uani 1 1 d . . . . .
H8A H 0.5344 0.6961 0.6823 0.030 Uiso 1 1 calc R U . . .
H8B H 0.3759 0.6565 0.7360 0.030 Uiso 1 1 calc R U . . .
H8C H 0.3315 0.7435 0.6765 0.030 Uiso 1 1 calc R U . . .
C9 C 0.1435(2) 0.57505(15) 0.63588(10) 0.0224(4) Uani 1 1 d . . . . .
H9A H 0.1086 0.5259 0.5976 0.034 Uiso 1 1 calc R U . . .
H9B H 0.0760 0.6401 0.6291 0.034 Uiso 1 1 calc R U . . .
H9C H 0.1134 0.5457 0.6836 0.034 Uiso 1 1 calc R U . . .
C10 C 0.7370(3) 0.38738(13) 0.65656(10) 0.0234(4) Uani 1 1 d . . . . .
H10A H 0.8716 0.3893 0.6543 0.035 Uiso 1 1 calc R U . . .
H10B H 0.6902 0.3384 0.6203 0.035 Uiso 1 1 calc R U . . .
H10C H 0.6983 0.3653 0.7052 0.035 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
O1 C3 1.237(2) . ?
N1 N2 1.4161(19) . ?
N1 C7 1.460(2) . ?
N1 H1 0.91(2) . ?
N2 C3 1.362(2) . ?
N2 H2 0.88(2) . ?
N4 C3 1.373(2) . ?
N4 C5 1.489(2) . ?
N4 H4 0.90(2) . ?
C5 C6 1.527(2) . ?
C5 C9 1.532(2) . ?
C5 C8 1.533(2) . ?
C6 C7 1.528(2) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C10 1.527(2) . ?
C7 H7A 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 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
N2 N1 C7 114.86(13) . . ?
N2 N1 H1 107.8(14) . . ?
C7 N1 H1 110.5(14) . . ?
C3 N2 N1 125.16(14) . . ?
C3 N2 H2 114.1(15) . . ?
N1 N2 H2 114.3(15) . . ?
C3 N4 C5 124.19(13) . . ?
C3 N4 H4 108.4(14) . . ?
C5 N4 H4 111.2(14) . . ?
O1 C3 N2 120.31(15) . . ?
O1 C3 N4 121.53(14) . . ?
N2 C3 N4 118.16(14) . . ?
N4 C5 C6 111.70(13) . . ?
N4 C5 C9 105.28(13) . . ?
C6 C5 C9 107.83(14) . . ?
N4 C5 C8 109.80(13) . . ?
C6 C5 C8 112.29(14) . . ?
C9 C5 C8 109.67(15) . . ?
C5 C6 C7 117.15(14) . . ?
C5 C6 H6A 108.0 . . ?
C7 C6 H6A 108.0 . . ?
C5 C6 H6B 108.0 . . ?
C7 C6 H6B 108.0 . . ?
H6A C6 H6B 107.3 . . ?
N1 C7 C10 107.42(14) . . ?
N1 C7 C6 113.75(14) . . ?
C10 C7 C6 110.09(14) . . ?
N1 C7 H7A 108.5 . . ?
C10 C7 H7A 108.5 . . ?
C6 C7 H7A 108.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C9 H9A 109.5 . . ?
C5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 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
C7 N1 N2 C3 -76.4(2) . . . . ?
N1 N2 C3 O1 -152.35(16) . . . . ?
N1 N2 C3 N4 26.7(2) . . . . ?
C5 N4 C3 O1 -136.26(17) . . . . ?
C5 N4 C3 N2 44.7(2) . . . . ?
C3 N4 C5 C6 -75.00(19) . . . . ?
C3 N4 C5 C9 168.23(15) . . . . ?
C3 N4 C5 C8 50.2(2) . . . . ?
N4 C5 C6 C7 61.56(19) . . . . ?
C9 C5 C6 C7 176.77(15) . . . . ?
C8 C5 C6 C7 -62.30(19) . . . . ?
N2 N1 C7 C10 -166.44(14) . . . . ?
N2 N1 C7 C6 71.46(18) . . . . ?
C5 C6 C7 N1 -59.0(2) . . . . ?
C5 C6 C7 C10 -179.65(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
N1 H1 N4 0.91(2) 2.34(2) 3.214(2) 162(2) 5_666
N2 H2 O1 0.88(2) 2.10(3) 2.9757(18) 172(2) 2_566
N4 H4 O1 0.90(2) 2.09(2) 2.9817(18) 171(2) 2_466

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

