# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1063500'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
1-(2-Bromophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Br N2 S'
_chemical_formula_weight         311.24

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'
Br Br -0.2901 2.4595 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.3156(7)
_cell_length_b                   8.5081(5)
_cell_length_c                   14.8996(9)
_cell_angle_alpha                90
_cell_angle_beta                 114.046(3)
_cell_angle_gamma                90
_cell_volume                     1425.73(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.450
_exptl_crystal_F_000             632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.010
_shelx_estimated_absorpt_T_min   0.410
_shelx_estimated_absorpt_T_max   0.557
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11792
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.780
_diffrn_reflns_theta_max         27.513
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3266
_reflns_number_gt                1848
_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-2013 (Sheldrick, 2013)'
_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)+(0.0684P)²+1.8472P] 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         3266
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1158
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1729
_refine_ls_wR_factor_gt          0.1457
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.29724(6) 0.27052(9) 0.34075(6) 0.1113(4) Uani 1 1 d . . . . .
S1 S 0.11641(12) 0.29876(15) 0.51985(8) 0.0647(4) Uani 1 1 d . . . . .
N1 N 0.0511(3) 0.1965(4) 0.3368(2) 0.0426(8) Uani 1 1 d . . . . .
N2 N -0.0426(3) 0.4182(4) 0.3568(2) 0.0531(9) Uani 1 1 d . . . . .
H2 H -0.0594 0.4757 0.3969 0.064 Uiso 1 1 calc R U . . .
C1 C 0.1360(4) 0.0719(5) 0.3784(3) 0.0471(10) Uani 1 1 d . . . . .
C2 C 0.2497(4) 0.0847(6) 0.3824(3) 0.0633(12) Uani 1 1 d . . . . .
C3 C 0.3295(5) -0.0390(8) 0.4180(4) 0.0827(17) Uani 1 1 d . . . . .
H3 H 0.4058 -0.0309 0.4201 0.099 Uiso 1 1 calc R U . . .
C4 C 0.2950(6) -0.1720(8) 0.4497(4) 0.0871(19) Uani 1 1 d . . . . .
H4 H 0.3481 -0.2552 0.4729 0.105 Uiso 1 1 calc R U . . .
C5 C 0.1842(6) -0.1854(6) 0.4481(4) 0.0813(17) Uani 1 1 d . . . . .
H5 H 0.1641 -0.2781 0.4706 0.098 Uiso 1 1 calc R U . . .
C6 C 0.0991(4) -0.0656(5) 0.4139(3) 0.0604(13) Uani 1 1 d . . . . .
H6 H 0.0240 -0.0747 0.4143 0.073 Uiso 1 1 calc R U . . .
C7 C 0.0367(3) 0.3060(4) 0.3973(3) 0.0422(9) Uani 1 1 d . . . . .
C8 C -0.1053(3) 0.4572(4) 0.2527(3) 0.0441(9) Uani 1 1 d . . . . .
C9 C -0.0904(4) 0.3220(5) 0.1950(3) 0.0520(10) Uani 1 1 d . . . . .
H9 H -0.1351 0.3215 0.1275 0.062 Uiso 1 1 calc R U . . .
C10 C -0.0178(4) 0.2034(5) 0.2339(3) 0.0449(9) Uani 1 1 d . . . . .
C11 C -0.0035(5) 0.0690(6) 0.1743(3) 0.0751(15) Uani 1 1 d . . . . .
H11A H -0.0544 0.0850 0.1062 0.113 Uiso 1 1 calc R U . . .
H11B H -0.0246 -0.0275 0.1965 0.113 Uiso 1 1 calc R U . . .
H11C H 0.0777 0.0636 0.1820 0.113 Uiso 1 1 calc R U . . .
C12 C -0.0514(6) 0.6063(6) 0.2330(4) 0.0813(16) Uani 1 1 d . . . . .
H12A H -0.0921 0.6347 0.1650 0.122 Uiso 1 1 calc R U . . .
H12B H 0.0312 0.5890 0.2480 0.122 Uiso 1 1 calc R U . . .
H12C H -0.0591 0.6896 0.2734 0.122 Uiso 1 1 calc R U . . .
C13 C -0.2356(4) 0.4852(6) 0.2296(4) 0.0758(15) Uani 1 1 d . . . . .
H13A H -0.2775 0.5088 0.1610 0.114 Uiso 1 1 calc R U . . .
H13B H -0.2430 0.5719 0.2680 0.114 Uiso 1 1 calc R U . . .
H13C H -0.2689 0.3925 0.2453 0.114 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
Br1 C2 1.877(5) . ?
S1 C7 1.686(4) . ?
N1 C7 1.357(5) . ?
N1 C10 1.419(5) . ?
N1 C1 1.439(5) . ?
N2 C7 1.322(5) . ?
N2 C8 1.462(5) . ?
N2 H2 0.8600 . ?
C1 C2 1.382(6) . ?
C1 C6 1.432(6) . ?
C2 C3 1.390(7) . ?
C3 C4 1.358(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.401(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.491(5) . ?
C8 C12 1.515(6) . ?
C8 C13 1.517(6) . ?
C9 C10 1.316(6) . ?
C9 H9 0.9300 . ?
C10 C11 1.501(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C7 N1 C10 120.4(3) . . ?
C7 N1 C1 119.2(3) . . ?
C10 N1 C1 120.3(3) . . ?
C7 N2 C8 128.3(3) . . ?
C7 N2 H2 115.8 . . ?
C8 N2 H2 115.8 . . ?
C2 C1 C6 121.1(4) . . ?
C2 C1 N1 120.4(4) . . ?
C6 C1 N1 118.5(4) . . ?
C1 C2 C3 120.2(5) . . ?
C1 C2 Br1 120.0(4) . . ?
C3 C2 Br1 119.8(4) . . ?
C4 C3 C2 119.4(5) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 121.1(5) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 122.9(6) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 115.2(5) . . ?
C5 C6 H6 122.4 . . ?
C1 C6 H6 122.4 . . ?
N2 C7 N1 117.7(3) . . ?
N2 C7 S1 121.1(3) . . ?
N1 C7 S1 121.2(3) . . ?
N2 C8 C9 107.5(3) . . ?
N2 C8 C12 108.2(3) . . ?
C9 C8 C12 111.6(4) . . ?
N2 C8 C13 109.2(4) . . ?
C9 C8 C13 111.0(3) . . ?
C12 C8 C13 109.4(4) . . ?
C10 C9 C8 124.0(4) . . ?
C10 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C9 C10 N1 120.5(3) . . ?
C9 C10 C11 123.1(4) . . ?
N1 C10 C11 116.4(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 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 C1 C2 -95.7(5) . . . . ?
C10 N1 C1 C2 85.1(5) . . . . ?
C7 N1 C1 C6 85.2(4) . . . . ?
C10 N1 C1 C6 -94.0(4) . . . . ?
C6 C1 C2 C3 2.3(6) . . . . ?
N1 C1 C2 C3 -176.7(4) . . . . ?
C6 C1 C2 Br1 -177.1(3) . . . . ?
N1 C1 C2 Br1 3.9(5) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
Br1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C3 C4 C5 C6 0.2(8) . . . . ?
C4 C5 C6 C1 1.4(7) . . . . ?
C2 C1 C6 C5 -2.6(6) . . . . ?
N1 C1 C6 C5 176.5(4) . . . . ?
C8 N2 C7 N1 -10.9(6) . . . . ?
C8 N2 C7 S1 169.5(3) . . . . ?
C10 N1 C7 N2 -0.3(5) . . . . ?
C1 N1 C7 N2 -179.5(4) . . . . ?
C10 N1 C7 S1 179.3(3) . . . . ?
C1 N1 C7 S1 0.1(5) . . . . ?
C7 N2 C8 C9 15.1(6) . . . . ?
C7 N2 C8 C12 -105.5(5) . . . . ?
C7 N2 C8 C13 135.6(4) . . . . ?
N2 C8 C9 C10 -9.6(6) . . . . ?
C12 C8 C9 C10 108.8(5) . . . . ?
C13 C8 C9 C10 -128.9(5) . . . . ?
C8 C9 C10 N1 1.2(7) . . . . ?
C8 C9 C10 C11 -179.5(4) . . . . ?
C7 N1 C10 C9 4.8(6) . . . . ?
C1 N1 C10 C9 -176.0(4) . . . . ?
C7 N1 C10 C11 -174.6(4) . . . . ?
C1 N1 C10 C11 4.6(6) . . . . ?

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 2.53 3.371(3) 164.4 3_566
C6 H6 S1 0.93 3.00 3.753(6) 139.7 3_556
C9 H9 S1 0.93 3.00 3.637(4) 127.3 4_565
C11 H11C Br1 0.96 3.02 3.663(5) 125.4 2_545

_refine_diff_density_max         0.773
_refine_diff_density_min         -0.809
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1063506'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
1-(2-Fluorophenyl)-4,4,6-trimethyl-3,4-dihydropyrimidine-2(1H)-thione
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 F N2 S'
_chemical_formula_weight         250.33

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'
F F 0.0171 0.0103 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.7432(8)
_cell_length_b                   7.1550(5)
_cell_length_c                   18.8125(14)
_cell_angle_alpha                90
_cell_angle_beta                 91.594(5)
_cell_angle_gamma                90
_cell_volume                     1310.96(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             528
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.238
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.949
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11164
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.166
_diffrn_reflns_theta_max         27.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3023
_reflns_number_gt                2001
_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-2013 (Sheldrick, 2013)'
_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)+(0.0812P)²+1.0273P] 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         3023
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0618
_refine_ls_wR_factor_ref         0.1920
_refine_ls_wR_factor_gt          0.1715
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.15149(8) 0.24343(11) 0.51357(4) 0.0522(3) Uani 1 1 d . . . . .
F1 F 0.4108(2) 0.2797(3) 0.37808(15) 0.0892(8) Uani 1 1 d . . . . .
N1 N 0.1383(2) 0.3849(3) 0.38247(12) 0.0492(6) Uani 1 1 d . . . . .
N2 N -0.0107(3) 0.1449(4) 0.40622(14) 0.0604(7) Uani 1 1 d . . . . .
H2 H -0.042(4) 0.057(5) 0.4392(19) 0.072 Uiso 1 1 d . U . . .
C1 C 0.2479(3) 0.5085(4) 0.40410(15) 0.0458(6) Uani 1 1 d . . . . .
C2 C 0.3827(3) 0.4560(4) 0.39921(16) 0.0530(7) Uani 1 1 d . . . . .
C3 C 0.4893(3) 0.5747(6) 0.4153(2) 0.0679(9) Uani 1 1 d . . . . .
H3 H 0.5797 0.5347 0.4119 0.081 Uiso 1 1 calc R U . . .
C4 C 0.4606(4) 0.7531(5) 0.43657(19) 0.0662(9) Uani 1 1 d . . . . .
H4 H 0.5317 0.8358 0.4475 0.079 Uiso 1 1 calc R U . . .
C5 C 0.3259(4) 0.8099(5) 0.4417(2) 0.0700(10) Uani 1 1 d . . . . .
H5 H 0.3064 0.9314 0.4559 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2209(3) 0.6888(5) 0.42619(18) 0.0574(8) Uani 1 1 d . . . . .
H6 H 0.1305 0.7279 0.4305 0.069 Uiso 1 1 calc R U . . .
C7 C 0.0889(3) 0.2579(4) 0.42961(15) 0.0448(6) Uani 1 1 d . . . . .
C8 C -0.0875(3) 0.1555(6) 0.33915(17) 0.0628(9) Uani 1 1 d . . . . .
C9 C -0.0140(5) 0.2789(6) 0.2902(2) 0.0874(14) Uani 1 1 d . . . . .
H9 H -0.066(5) 0.288(6) 0.244(3) 0.105 Uiso 1 1 d . U . . .
C10 C 0.0897(4) 0.3897(5) 0.31044(18) 0.0667(9) Uani 1 1 d . . . . .
C11 C 0.1621(5) 0.5082(6) 0.2610(2) 0.0918(14) Uani 1 1 d . . . . .
H12A H 0.1228 0.4927 0.2140 0.138 Uiso 1 1 calc R U . . .
H12B H 0.2573 0.4736 0.2612 0.138 Uiso 1 1 calc R U . . .
H12C H 0.1539 0.6364 0.2753 0.138 Uiso 1 1 calc R U . . .
C12 C -0.2295(5) 0.2052(14) 0.3547(3) 0.189(4) Uani 1 1 d . . . . .
H13A H -0.2891 0.1672 0.3159 0.284 Uiso 1 1 calc R U . . .
H13B H -0.2362 0.3380 0.3611 0.284 Uiso 1 1 calc R U . . .
H13C H -0.2561 0.1431 0.3974 0.284 Uiso 1 1 calc R U . . .
C13 C -0.0860(9) -0.0398(9) 0.3064(3) 0.158(3) Uani 1 1 d . . . . .
H14A H -0.1136 -0.0324 0.2571 0.237 Uiso 1 1 calc R U . . .
H14B H -0.1485 -0.1191 0.3309 0.237 Uiso 1 1 calc R U . . .
H14C H 0.0051 -0.0907 0.3106 0.237 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 C7 1.680(3) . ?
F1 C2 1.353(4) . ?
N1 C7 1.367(4) . ?
N1 C10 1.423(4) . ?
N1 C1 1.436(4) . ?
N2 C7 1.329(4) . ?
N2 C8 1.451(4) . ?
N2 H2 0.94(4) . ?
C1 C2 1.372(4) . ?
C1 C6 1.383(4) . ?
C2 C3 1.369(5) . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(5) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C12 1.465(6) . ?
C8 C9 1.475(5) . ?
C8 C13 1.527(7) . ?
C9 C10 1.331(5) . ?
C9 H9 1.00(5) . ?
C10 C11 1.455(5) . ?
C11 H12A 0.9600 . ?
C11 H12B 0.9600 . ?
C11 H12C 0.9600 . ?
C12 H13A 0.9600 . ?
C12 H13B 0.9600 . ?
C12 H13C 0.9600 . ?
C13 H14A 0.9600 . ?
C13 H14B 0.9600 . ?
C13 H14C 0.9600 . ?

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
C7 N1 C10 121.3(2) . . ?
C7 N1 C1 119.9(2) . . ?
C10 N1 C1 118.7(2) . . ?
C7 N2 C8 127.6(3) . . ?
C7 N2 H2 116(2) . . ?
C8 N2 H2 116(2) . . ?
C2 C1 C6 117.8(3) . . ?
C2 C1 N1 121.2(3) . . ?
C6 C1 N1 120.9(3) . . ?
F1 C2 C3 119.0(3) . . ?
F1 C2 C1 118.5(3) . . ?
C3 C2 C1 122.5(3) . . ?
C4 C3 C2 118.9(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N2 C7 N1 117.2(3) . . ?
N2 C7 S1 121.1(2) . . ?
N1 C7 S1 121.7(2) . . ?
N2 C8 C12 107.8(4) . . ?
N2 C8 C9 109.0(3) . . ?
C12 C8 C9 117.2(4) . . ?
N2 C8 C13 107.0(4) . . ?
C12 C8 C13 108.8(6) . . ?
C9 C8 C13 106.6(4) . . ?
C10 C9 C8 123.7(3) . . ?
C10 C9 H9 125(3) . . ?
C8 C9 H9 110(3) . . ?
C9 C10 N1 119.2(3) . . ?
C9 C10 C11 122.8(3) . . ?
N1 C10 C11 117.9(3) . . ?
C10 C11 H12A 109.5 . . ?
C10 C11 H12B 109.5 . . ?
H12A C11 H12B 109.5 . . ?
C10 C11 H12C 109.5 . . ?
H12A C11 H12C 109.5 . . ?
H12B C11 H12C 109.5 . . ?
C8 C12 H13A 109.5 . . ?
C8 C12 H13B 109.5 . . ?
H13A C12 H13B 109.5 . . ?
C8 C12 H13C 109.5 . . ?
H13A C12 H13C 109.5 . . ?
H13B C12 H13C 109.5 . . ?
C8 C13 H14A 109.5 . . ?
C8 C13 H14B 109.5 . . ?
H14A C13 H14B 109.5 . . ?
C8 C13 H14C 109.5 . . ?
H14A C13 H14C 109.5 . . ?
H14B C13 H14C 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 C1 C2 86.8(4) . . . . ?
C10 N1 C1 C2 -89.1(4) . . . . ?
C7 N1 C1 C6 -97.4(3) . . . . ?
C10 N1 C1 C6 86.7(4) . . . . ?
C6 C1 C2 F1 179.6(3) . . . . ?
N1 C1 C2 F1 -4.5(4) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
N1 C1 C2 C3 175.9(3) . . . . ?
F1 C2 C3 C4 179.9(3) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 C5 0.3(6) . . . . ?
C3 C4 C5 C6 0.4(6) . . . . ?
C4 C5 C6 C1 -0.9(6) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
N1 C1 C6 C5 -175.2(3) . . . . ?
C8 N2 C7 N1 -9.1(5) . . . . ?
C8 N2 C7 S1 171.2(3) . . . . ?
C10 N1 C7 N2 -3.0(4) . . . . ?
C1 N1 C7 N2 -178.8(3) . . . . ?
C10 N1 C7 S1 176.7(2) . . . . ?
C1 N1 C7 S1 0.9(4) . . . . ?
C7 N2 C8 C12 -112.1(5) . . . . ?
C7 N2 C8 C9 16.0(5) . . . . ?
C7 N2 C8 C13 130.9(5) . . . . ?
N2 C8 C9 C10 -12.3(6) . . . . ?
C12 C8 C9 C10 110.4(6) . . . . ?
C13 C8 C9 C10 -127.5(5) . . . . ?
C8 C9 C10 N1 3.0(7) . . . . ?
C8 C9 C10 C11 179.1(4) . . . . ?
C7 N1 C10 C9 5.7(5) . . . . ?
C1 N1 C10 C9 -178.4(4) . . . . ?
C7 N1 C10 C11 -170.5(3) . . . . ?
C1 N1 C10 C11 5.4(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 0.94(4) 2.57(4) 3.463(3) 159(3) 3_556
C6 H6 S1 0.93 2.98 3.861(3) 159.6 3_566

_refine_diff_density_max         0.922
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1419338'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Cl N3 O2 S'
_chemical_formula_weight         311.78

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.3088(5)
_cell_length_b                   10.1010(8)
_cell_length_c                   12.0187(10)
_cell_angle_alpha                91.338(4)
_cell_angle_beta                 98.933(3)
_cell_angle_gamma                99.800(4)
_cell_volume                     744.59(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.896
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11708
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.717
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             3177
_reflns_number_gt                2278
_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-2014/7 (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)+(0.0632P)²+0.3190P] 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         3177
_refine_ls_number_parameters     184
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1387
_refine_ls_wR_factor_gt          0.1248
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Cl1 Cl 0.09505(11) 0.08714(8) 0.34614(6) 0.0639(2) Uani 1 1 d . . . . .
S1 S 0.57261(12) 0.01823(7) 0.18705(5) 0.0522(2) Uani 1 1 d . . . . .
O1 O 1.1129(4) 0.3822(3) 0.5086(2) 0.0782(7) Uani 1 1 d . . . . .
O2 O 1.0296(5) 0.3211(4) 0.6670(2) 0.1202(12) Uani 1 1 d . . . . .
N1 N 0.9848(4) 0.3276(3) 0.5661(2) 0.0641(7) Uani 1 1 d . . . . .
N2 N 0.4286(3) 0.2449(2) 0.22980(15) 0.0443(5) Uani 1 1 d . . . . .
N3 N 0.3528(4) 0.1604(2) 0.04640(17) 0.0560(6) Uani 1 1 d . . . . .
H3A H 0.3744 0.1031 -0.0029 0.067 Uiso 1 1 calc R U . . .
C1 C 0.4979(4) 0.2260(2) 0.34714(18) 0.0405(5) Uani 1 1 d . . . . .
C2 C 0.3546(4) 0.1565(3) 0.4104(2) 0.0435(6) Uani 1 1 d . . . . .
C3 C 0.4177(5) 0.1423(3) 0.5246(2) 0.0520(7) Uani 1 1 d . . . . .
H3 H 0.3206 0.0945 0.5663 0.062 Uiso 1 1 calc R U . . .
C4 C 0.6240(5) 0.1988(3) 0.5757(2) 0.0523(7) Uani 1 1 d . . . . .
H4 H 0.6682 0.1907 0.6524 0.063 Uiso 1 1 calc R U . . .
C5 C 0.7629(4) 0.2672(3) 0.5122(2) 0.0468(6) Uani 1 1 d . . . . .
C6 C 0.7050(4) 0.2821(3) 0.3979(2) 0.0457(6) Uani 1 1 d . . . . .
H6 H 0.8039 0.3288 0.3565 0.055 Uiso 1 1 calc R U . . .
C7 C 0.4436(4) 0.1473(3) 0.15174(19) 0.0428(6) Uani 1 1 d . . . . .
C8 C 0.2206(5) 0.2595(3) 0.0030(2) 0.0596(8) Uani 1 1 d . . . . .
C9 C 0.2381(6) 0.3652(4) 0.0937(3) 0.0769(10) Uani 1 1 d . . . . .
H9 H 0.1784 0.4413 0.0749 0.092 Uiso 1 1 calc R U . . .
C10 C 0.3326(5) 0.3588(3) 0.1995(2) 0.0580(7) Uani 1 1 d . . . . .
C11 C 0.3539(7) 0.4677(3) 0.2852(3) 0.0796(10) Uani 1 1 d . . . . .
H11A H 0.2880 0.5397 0.2526 0.119 Uiso 1 1 calc R U . . .
H11B H 0.5055 0.5002 0.3128 0.119 Uiso 1 1 calc R U . . .
H11C H 0.2823 0.4346 0.3465 0.119 Uiso 1 1 calc R U . . .
C12 C 0.3253(9) 0.3276(4) -0.0932(3) 0.1085(16) Uani 1 1 d . . . . .
H12A H 0.4725 0.3698 -0.0647 0.163 Uiso 1 1 calc R U . . .
H12B H 0.2435 0.3942 -0.1232 0.163 Uiso 1 1 calc R U . . .
H12C H 0.3253 0.2612 -0.1517 0.163 Uiso 1 1 calc R U . . .
C13 C -0.0030(7) 0.1884(4) -0.0439(5) 0.1189(18) Uani 1 1 d . . . . .
H13A H -0.0840 0.2505 -0.0828 0.178 Uiso 1 1 calc R U . . .
H13B H -0.0749 0.1525 0.0164 0.178 Uiso 1 1 calc R U . . .
H13C H 0.0057 0.1164 -0.0956 0.178 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
Cl1 C2 1.721(3) . ?
S1 C7 1.680(3) . ?
O1 N1 1.214(3) . ?
O2 N1 1.208(3) . ?
N1 C5 1.470(4) . ?
N2 C7 1.370(3) . ?
N2 C10 1.419(3) . ?
N2 C1 1.437(3) . ?
N3 C7 1.325(3) . ?
N3 C8 1.464(4) . ?
N3 H3A 0.8600 . ?
C1 C6 1.373(3) . ?
C1 C2 1.382(4) . ?
C2 C3 1.386(3) . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.362(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.487(4) . ?
C8 C13 1.487(5) . ?
C8 C12 1.538(5) . ?
C9 C10 1.326(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.464(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
O2 N1 O1 123.1(3) . . ?
O2 N1 C5 117.5(3) . . ?
O1 N1 C5 119.4(2) . . ?
C7 N2 C10 122.2(2) . . ?
C7 N2 C1 118.7(2) . . ?
C10 N2 C1 118.86(19) . . ?
C7 N3 C8 128.5(2) . . ?
C7 N3 H3A 115.7 . . ?
C8 N3 H3A 115.7 . . ?
C6 C1 C2 119.7(2) . . ?
C6 C1 N2 119.8(2) . . ?
C2 C1 N2 120.5(2) . . ?
C1 C2 C3 120.8(2) . . ?
C1 C2 Cl1 119.34(18) . . ?
C3 C2 Cl1 119.9(2) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 118.8(2) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C4 C5 C6 122.8(2) . . ?
C4 C5 N1 119.2(2) . . ?
C6 C5 N1 118.0(3) . . ?
C1 C6 C5 118.2(2) . . ?
C1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
N3 C7 N2 116.6(2) . . ?
N3 C7 S1 121.50(19) . . ?
N2 C7 S1 121.86(18) . . ?
N3 C8 C9 108.1(2) . . ?
N3 C8 C13 109.0(3) . . ?
C9 C8 C13 116.5(4) . . ?
N3 C8 C12 107.2(3) . . ?
C9 C8 C12 107.0(3) . . ?
C13 C8 C12 108.7(3) . . ?
C10 C9 C8 124.8(3) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 N2 118.7(3) . . ?
C9 C10 C11 123.0(3) . . ?
N2 C10 C11 118.3(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 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 N2 C1 C6 95.6(3) . . . . ?
C10 N2 C1 C6 -89.0(3) . . . . ?
C7 N2 C1 C2 -87.1(3) . . . . ?
C10 N2 C1 C2 88.4(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
N2 C1 C2 C3 -177.6(2) . . . . ?
C6 C1 C2 Cl1 179.77(19) . . . . ?
N2 C1 C2 Cl1 2.4(3) . . . . ?
C1 C2 C3 C4 0.6(4) . . . . ?
Cl1 C2 C3 C4 -179.3(2) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 N1 -179.7(2) . . . . ?
O2 N1 C5 C4 -4.7(4) . . . . ?
O1 N1 C5 C4 176.0(3) . . . . ?
O2 N1 C5 C6 175.7(3) . . . . ?
O1 N1 C5 C6 -3.7(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N2 C1 C6 C5 177.0(2) . . . . ?
C4 C5 C6 C1 0.5(4) . . . . ?
N1 C5 C6 C1 -179.9(2) . . . . ?
C8 N3 C7 N2 -5.9(4) . . . . ?
C8 N3 C7 S1 174.7(2) . . . . ?
C10 N2 C7 N3 -3.6(4) . . . . ?
C1 N2 C7 N3 171.7(2) . . . . ?
C10 N2 C7 S1 175.8(2) . . . . ?
C1 N2 C7 S1 -8.9(3) . . . . ?
C7 N3 C8 C9 11.4(4) . . . . ?
C7 N3 C8 C13 -116.1(4) . . . . ?
C7 N3 C8 C12 126.4(3) . . . . ?
N3 C8 C9 C10 -8.6(5) . . . . ?
C13 C8 C9 C10 114.5(4) . . . . ?
C12 C8 C9 C10 -123.7(4) . . . . ?
C8 C9 C10 N2 1.2(6) . . . . ?
C8 C9 C10 C11 177.5(3) . . . . ?
C7 N2 C10 C9 5.8(4) . . . . ?
C1 N2 C10 C9 -169.5(3) . . . . ?
C7 N2 C10 C11 -170.7(3) . . . . ?
C1 N2 C10 C11 14.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A S1 0.86 2.60 3.437(2) 164.8 2_655
C11 H11C O1 0.96 2.39 3.345(5) 172.5 1_455

_refine_diff_density_max         0.794
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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 1419339'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   12.0474(15)
_cell_length_b                   9.4787(9)
_cell_length_c                   14.3337(17)
_cell_angle_alpha                90
_cell_angle_beta                 107.574(3)
_cell_angle_gamma                90
_cell_volume                     1560.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.957
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12620
_diffrn_reflns_av_unetI/netI     0.0722
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.615
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3398
_reflns_number_gt                1618
_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-2014/7 (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)+(0.0662P)²+0.0851P] 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         3398
_refine_ls_number_parameters     194
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1401
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1612
_refine_ls_wR_factor_gt          0.1314
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.60428(8) 0.81086(9) 0.51482(6) 0.0688(3) Uani 1 1 d . . . . .
O1 O 0.7438(3) 0.8102(3) 0.2944(2) 0.1246(12) Uani 1 1 d . . . . .
O2 O 0.8897(3) 0.7700(3) 0.4183(2) 0.1233(11) Uani 1 1 d . . . . .
O3 O 0.8413(3) 0.2664(3) 0.4743(2) 0.1080(10) Uani 1 1 d . . . . .
N1 N 0.7945(3) 0.7404(3) 0.3625(2) 0.0783(9) Uani 1 1 d . . . . .
N2 N 0.5454(2) 0.7186(2) 0.33100(17) 0.0529(6) Uani 1 1 d . . . . .
N3 N 0.4584(2) 0.9237(3) 0.35659(17) 0.0673(8) Uani 1 1 d . . . . .
H3A H 0.4430 0.9797 0.3982 0.081 Uiso 1 1 calc R U . . .
C1 C 0.6216(3) 0.6035(3) 0.3693(2) 0.0504(7) Uani 1 1 d . . . . .
C2 C 0.7406(3) 0.6090(3) 0.3839(2) 0.0557(8) Uani 1 1 d . . . . .
C3 C 0.8122(3) 0.4980(4) 0.4203(2) 0.0711(10) Uani 1 1 d . . . . .
H3 H 0.8920 0.5062 0.4309 0.085 Uiso 1 1 calc R U . . .
C4 C 0.7657(3) 0.3735(4) 0.4413(2) 0.0710(10) Uani 1 1 d . . . . .
C5 C 0.6477(3) 0.3649(4) 0.4298(2) 0.0706(10) Uani 1 1 d . . . . .
H5 H 0.6159 0.2825 0.4460 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5777(3) 0.4801(3) 0.3940(2) 0.0626(9) Uani 1 1 d . . . . .
H6 H 0.4984 0.4740 0.3863 0.075 Uiso 1 1 calc R U . . .
C7 C 0.7970(5) 0.1339(5) 0.4887(4) 0.144(2) Uani 1 1 d . . . . .
H7A H 0.7401 0.1042 0.4293 0.215 Uiso 1 1 calc R U . . .
H7B H 0.7613 0.1404 0.5401 0.215 Uiso 1 1 calc R U . . .
H7C H 0.8594 0.0665 0.5066 0.215 Uiso 1 1 calc R U . . .
C8 C 0.5310(3) 0.8200(3) 0.3939(2) 0.0514(7) Uani 1 1 d . . . . .
C9 C 0.4005(3) 0.9562(3) 0.2533(2) 0.0652(9) Uani 1 1 d . . . . .
C10 C 0.4184(3) 0.8346(4) 0.1942(2) 0.0778(10) Uani 1 1 d . . . . .
H10 H 0.3791 0.8355 0.1275 0.093 Uiso 1 1 calc R U . . .
C11 C 0.4855(3) 0.7261(3) 0.2291(2) 0.0609(9) Uani 1 1 d . . . . .
C12 C 0.5042(4) 0.6050(4) 0.1679(2) 0.0906(12) Uani 1 1 d . . . . .
H12A H 0.4784 0.5191 0.1902 0.136 Uiso 1 1 calc R U . . .
H12B H 0.5855 0.5976 0.1737 0.136 Uiso 1 1 calc R U . . .
H12C H 0.4606 0.6209 0.1007 0.136 Uiso 1 1 calc R U . . .
C13 C 0.4575(4) 1.0881(4) 0.2290(3) 0.1071(15) Uani 1 1 d . . . . .
H13A H 0.5391 1.0713 0.2408 0.161 Uiso 1 1 calc R U . . .
H13B H 0.4470 1.1647 0.2693 0.161 Uiso 1 1 calc R U . . .
H13C H 0.4223 1.1118 0.1613 0.161 Uiso 1 1 calc R U . . .
C14 C 0.2731(3) 0.9832(5) 0.2383(3) 0.1233(16) Uani 1 1 d . . . . .
H14A H 0.2411 0.9072 0.2663 0.185 Uiso 1 1 calc R U . . .
H14B H 0.2329 0.9894 0.1695 0.185 Uiso 1 1 calc R U . . .
H14C H 0.2640 1.0702 0.2695 0.185 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 C8 1.693(3) . ?
O1 N1 1.185(4) . ?
O2 N1 1.216(4) . ?
O3 C4 1.351(4) . ?
O3 C7 1.404(6) . ?
N1 C2 1.479(4) . ?
N2 C8 1.364(3) . ?
N2 C11 1.422(4) . ?
N2 C1 1.425(3) . ?
N3 C8 1.317(3) . ?
N3 C9 1.466(4) . ?
N3 H3A 0.8600 . ?
C1 C6 1.373(4) . ?
C1 C2 1.386(4) . ?
C2 C3 1.360(4) . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(5) . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.485(4) . ?
C9 C14 1.506(5) . ?
C9 C13 1.517(5) . ?
C10 C11 1.311(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.502(4) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?

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 O3 C7 118.6(4) . . ?
O1 N1 O2 124.2(4) . . ?
O1 N1 C2 119.4(3) . . ?
O2 N1 C2 116.3(3) . . ?
C8 N2 C11 121.2(2) . . ?
C8 N2 C1 118.7(2) . . ?
C11 N2 C1 120.1(2) . . ?
C8 N3 C9 128.5(2) . . ?
C8 N3 H3A 115.7 . . ?
C9 N3 H3A 115.7 . . ?
C6 C1 C2 117.0(3) . . ?
C6 C1 N2 119.9(3) . . ?
C2 C1 N2 123.1(3) . . ?
C3 C2 C1 122.4(3) . . ?
C3 C2 N1 117.6(3) . . ?
C1 C2 N1 120.0(3) . . ?
C2 C3 C4 119.6(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
O3 C4 C3 116.5(4) . . ?
O3 C4 C5 123.8(4) . . ?
C3 C4 C5 119.7(3) . . ?
C6 C5 C4 119.2(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C1 C6 C5 122.1(3) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
O3 C7 H7A 109.5 . . ?
O3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N3 C8 N2 117.3(2) . . ?
N3 C8 S1 122.1(2) . . ?
N2 C8 S1 120.6(2) . . ?
N3 C9 C10 107.8(2) . . ?
N3 C9 C14 109.5(3) . . ?
C10 C9 C14 111.6(3) . . ?
N3 C9 C13 107.2(3) . . ?
C10 C9 C13 110.8(3) . . ?
C14 C9 C13 109.8(3) . . ?
C11 C10 C9 124.8(3) . . ?
C11 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C10 C11 N2 119.6(3) . . ?
C10 C11 C12 124.1(3) . . ?
N2 C11 C12 116.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C8 N2 C1 C6 94.1(3) . . . . ?
C11 N2 C1 C6 -85.5(3) . . . . ?
C8 N2 C1 C2 -85.6(3) . . . . ?
C11 N2 C1 C2 94.7(3) . . . . ?
C6 C1 C2 C3 0.5(4) . . . . ?
N2 C1 C2 C3 -179.8(3) . . . . ?
C6 C1 C2 N1 -177.7(3) . . . . ?
N2 C1 C2 N1 2.0(4) . . . . ?
O1 N1 C2 C3 144.7(4) . . . . ?
O2 N1 C2 C3 -36.1(4) . . . . ?
O1 N1 C2 C1 -37.1(5) . . . . ?
O2 N1 C2 C1 142.1(3) . . . . ?
C1 C2 C3 C4 1.8(5) . . . . ?
N1 C2 C3 C4 -180.0(3) . . . . ?
C7 O3 C4 C3 -174.6(3) . . . . ?
C7 O3 C4 C5 6.7(5) . . . . ?
C2 C3 C4 O3 178.0(3) . . . . ?
C2 C3 C4 C5 -3.2(5) . . . . ?
O3 C4 C5 C6 -179.0(3) . . . . ?
C3 C4 C5 C6 2.3(5) . . . . ?
C2 C1 C6 C5 -1.4(4) . . . . ?
N2 C1 C6 C5 178.9(3) . . . . ?
C4 C5 C6 C1 0.0(5) . . . . ?
C9 N3 C8 N2 -8.5(5) . . . . ?
C9 N3 C8 S1 171.5(3) . . . . ?
C11 N2 C8 N3 0.8(4) . . . . ?
C1 N2 C8 N3 -178.8(3) . . . . ?
C11 N2 C8 S1 -179.1(2) . . . . ?
C1 N2 C8 S1 1.2(4) . . . . ?
C8 N3 C9 C10 11.0(5) . . . . ?
C8 N3 C9 C14 132.6(4) . . . . ?
C8 N3 C9 C13 -108.3(4) . . . . ?
N3 C9 C10 C11 -7.0(5) . . . . ?
C14 C9 C10 C11 -127.3(4) . . . . ?
C13 C9 C10 C11 110.0(4) . . . . ?
C9 C10 C11 N2 1.4(6) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C8 N2 C11 C10 2.4(5) . . . . ?
C1 N2 C11 C10 -177.9(3) . . . . ?
C8 N2 C11 C12 -177.3(3) . . . . ?
C1 N2 C11 C12 2.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A S1 0.86 2.50 3.337(3) 165.0 3_676
C5 H5 S1 0.93 3.01 3.752(4) 138.4 3_666

_refine_diff_density_max         0.217
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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 1419340'
_audit_update_record             
;
2015-08-18 deposited with the CCDC.
2016-08-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H13 Cl3 N2 S'
_chemical_formula_weight         335.66

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'
Cl Cl 0.1484 0.1585 '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                   15.2154(11)
_cell_length_b                   11.9065(9)
_cell_length_c                   17.0387(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3086.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             1376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.260
_exptl_absorpt_coefficient_mu    0.716
_shelx_estimated_absorpt_T_min   0.773
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14207
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.391
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3366
_reflns_number_gt                2843
_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-2014/7 (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)+(0.0387P)²+1.1215P] 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         3366
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0364
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0809
_refine_ls_wR_factor_gt          0.0741
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_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
Cl1 Cl 0.39218(3) 0.61202(3) 0.21947(3) 0.05154(13) Uani 1 1 d . . . . .
Cl2 Cl 0.50610(4) 0.29347(5) 0.02010(3) 0.06922(17) Uani 1 1 d . . . . .
Cl3 Cl 0.37554(4) 0.17567(4) 0.30106(3) 0.06117(15) Uani 1 1 d . . . . .
S1 S 0.52060(2) 0.43730(4) 0.37625(2) 0.03749(11) Uani 1 1 d . . . . .
N1 N 0.35402(8) 0.42185(11) 0.32821(7) 0.0336(3) Uani 1 1 d . . . . .
N2 N 0.37523(8) 0.47812(13) 0.45587(8) 0.0426(3) Uani 1 1 d . . . . .
H2 H 0.4118 0.4915 0.4932 0.051 Uiso 1 1 calc R U . . .
C1 C 0.39080(9) 0.39081(12) 0.25424(8) 0.0319(3) Uani 1 1 d . . . . .
C2 C 0.41275(10) 0.47251(12) 0.19885(9) 0.0338(3) Uani 1 1 d . . . . .
C3 C 0.44987(11) 0.44413(14) 0.12724(9) 0.0395(4) Uani 1 1 d . . . . .
H3 H 0.4654 0.4992 0.0911 0.047 Uiso 1 1 calc R U . . .
C4 C 0.46317(11) 0.33172(15) 0.11100(9) 0.0412(4) Uani 1 1 d . . . . .
C5 C 0.44126(11) 0.24772(14) 0.16338(10) 0.0429(4) Uani 1 1 d . . . . .
H5 H 0.4505 0.1725 0.1511 0.052 Uiso 1 1 calc R U . . .
C6 C 0.40518(10) 0.27878(13) 0.23468(9) 0.0378(3) Uani 1 1 d . . . . .
C7 C 0.41072(10) 0.44711(12) 0.38842(8) 0.0309(3) Uani 1 1 d . . . . .
C8 C 0.28180(10) 0.49289(15) 0.47582(9) 0.0398(4) Uani 1 1 d . . . . .
C9 C 0.22824(10) 0.45421(15) 0.40732(10) 0.0447(4) Uani 1 1 d . . . . .
H9 H 0.1675 0.4519 0.4134 0.054 Uiso 1 1 calc R U . . .
C10 C 0.26088(10) 0.42308(13) 0.33882(9) 0.0374(3) Uani 1 1 d . . . . .
C11 C 0.20637(12) 0.38921(18) 0.26940(11) 0.0541(5) Uani 1 1 d . . . . .
H11A H 0.2181 0.4391 0.2264 0.081 Uiso 1 1 calc R U . . .
H11B H 0.1452 0.3931 0.2830 0.081 Uiso 1 1 calc R U . . .
H11C H 0.2210 0.3137 0.2544 0.081 Uiso 1 1 calc R U . . .
C12 C 0.26520(15) 0.61672(18) 0.49300(15) 0.0689(6) Uani 1 1 d . . . . .
H12A H 0.3006 0.6398 0.5368 0.103 Uiso 1 1 calc R U . . .
H12B H 0.2042 0.6277 0.5053 0.103 Uiso 1 1 calc R U . . .
H12C H 0.2803 0.6607 0.4477 0.103 Uiso 1 1 calc R U . . .
C13 C 0.26277(14) 0.4222(2) 0.54878(11) 0.0603(5) Uani 1 1 d . . . . .
H13A H 0.2972 0.4495 0.5920 0.090 Uiso 1 1 calc R U . . .
H13B H 0.2777 0.3452 0.5386 0.090 Uiso 1 1 calc R U . . .
H13C H 0.2015 0.4274 0.5616 0.090 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
Cl1 C2 1.7265(15) . ?
Cl2 C4 1.7417(16) . ?
Cl3 C6 1.7291(16) . ?
S1 C7 1.6886(15) . ?
N1 C7 1.3738(18) . ?
N1 C1 1.4277(18) . ?
N1 C10 1.4287(19) . ?
N2 C7 1.3224(19) . ?
N2 C8 1.472(2) . ?
N2 H2 0.8600 . ?
C1 C6 1.392(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.382(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C5 C6 1.383(2) . ?
C5 H5 0.9300 . ?
C8 C9 1.496(2) . ?
C8 C12 1.524(3) . ?
C8 C13 1.529(3) . ?
C9 C10 1.322(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.500(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
C7 N1 C1 118.01(12) . . ?
C7 N1 C10 121.76(12) . . ?
C1 N1 C10 120.21(12) . . ?
C7 N2 C8 128.93(13) . . ?
C7 N2 H2 115.5 . . ?
C8 N2 H2 115.5 . . ?
C6 C1 C2 117.91(14) . . ?
C6 C1 N1 121.40(13) . . ?
C2 C1 N1 120.68(13) . . ?
C3 C2 C1 121.52(14) . . ?
C3 C2 Cl1 119.17(12) . . ?
C1 C2 Cl1 119.31(12) . . ?
C4 C3 C2 118.17(15) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 122.46(14) . . ?
C5 C4 Cl2 118.41(13) . . ?
C3 C4 Cl2 119.10(13) . . ?
C4 C5 C6 118.00(15) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C5 C6 C1 121.92(14) . . ?
C5 C6 Cl3 119.21(12) . . ?
C1 C6 Cl3 118.86(12) . . ?
N2 C7 N1 116.97(13) . . ?
N2 C7 S1 122.04(11) . . ?
N1 C7 S1 120.99(11) . . ?
N2 C8 C9 108.01(12) . . ?
N2 C8 C12 108.66(15) . . ?
C9 C8 C12 110.93(15) . . ?
N2 C8 C13 107.74(14) . . ?
C9 C8 C13 111.20(15) . . ?
C12 C8 C13 110.19(16) . . ?
C10 C9 C8 124.79(14) . . ?
C10 C9 H9 117.6 . . ?
C8 C9 H9 117.6 . . ?
C9 C10 N1 119.17(14) . . ?
C9 C10 C11 124.34(15) . . ?
N1 C10 C11 116.49(14) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C8 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 C1 C6 93.44(17) . . . . ?
C10 N1 C1 C6 -84.85(18) . . . . ?
C7 N1 C1 C2 -87.17(17) . . . . ?
C10 N1 C1 C2 94.55(17) . . . . ?
C6 C1 C2 C3 -1.7(2) . . . . ?
N1 C1 C2 C3 178.92(14) . . . . ?
C6 C1 C2 Cl1 177.64(11) . . . . ?
N1 C1 C2 Cl1 -1.77(19) . . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
Cl1 C2 C3 C4 -177.98(12) . . . . ?
C2 C3 C4 C5 -0.3(2) . . . . ?
C2 C3 C4 Cl2 177.76(12) . . . . ?
C3 C4 C5 C6 -0.4(2) . . . . ?
Cl2 C4 C5 C6 -178.43(12) . . . . ?
C4 C5 C6 C1 0.0(2) . . . . ?
C4 C5 C6 Cl3 179.09(13) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
N1 C1 C6 C5 -179.61(14) . . . . ?
C2 C1 C6 Cl3 -178.10(11) . . . . ?
N1 C1 C6 Cl3 1.3(2) . . . . ?
C8 N2 C7 N1 -1.9(3) . . . . ?
C8 N2 C7 S1 178.74(14) . . . . ?
C1 N1 C7 N2 178.50(14) . . . . ?
C10 N1 C7 N2 -3.2(2) . . . . ?
C1 N1 C7 S1 -2.12(19) . . . . ?
C10 N1 C7 S1 176.14(11) . . . . ?
C7 N2 C8 C9 6.1(2) . . . . ?
C7 N2 C8 C12 -114.3(2) . . . . ?
C7 N2 C8 C13 126.30(19) . . . . ?
N2 C8 C9 C10 -6.0(2) . . . . ?
C12 C8 C9 C10 113.0(2) . . . . ?
C13 C8 C9 C10 -124.0(2) . . . . ?
C8 C9 C10 N1 2.1(3) . . . . ?
C8 C9 C10 C11 -177.22(17) . . . . ?
C7 N1 C10 C9 3.1(2) . . . . ?
C1 N1 C10 C9 -178.69(15) . . . . ?
C7 N1 C10 C11 -177.50(15) . . . . ?
C1 N1 C10 C11 0.7(2) . . . . ?

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 2.59 3.4219(14) 162.2 5_666
C5 H5 S1 0.93 2.87 3.8017(17) 176.3 3_645
C11 H11C Cl3 0.96 2.98 3.658(2) 128.9 .

_refine_diff_density_max         0.225
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.042

