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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_s2367
_database_code_depnum_ccdc_archive 'CCDC 1504146'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H15 Cl N2 S'
_chemical_formula_weight         266.78

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.214(2)
_cell_length_b                   9.8017(14)
_cell_length_c                   19.392(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.548(4)
_cell_angle_gamma                90.00
_cell_volume                     2689.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2691
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.01

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.8776
_exptl_absorpt_correction_T_max  0.9514

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24935
_diffrn_reflns_av_R_equivalents  0.0568
_diffrn_reflns_av_sigmaI/netI    0.0808
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         27.87
_reflns_number_total             6406
_reflns_number_gt                4205
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6406
_refine_ls_number_parameters     309
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0499
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.934
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.13731(5) 0.65421(6) 0.48360(3) 0.02081(16) Uani 1 1 d . . .
Cl1 Cl 0.15563(5) 0.92965(6) 0.61997(3) 0.02850(17) Uani 1 1 d . . .
N11 N 0.19941(14) 0.4973(2) 0.58934(10) 0.0220(5) Uani 1 1 d . . .
H1A H 0.2478 0.4807 0.5655 0.026 Uiso 1 1 calc R . .
N12 N 0.08036(14) 0.64517(19) 0.61161(10) 0.0192(5) Uani 1 1 d . . .
C101 C 0.19155(19) 0.4152(3) 0.65210(13) 0.0252(6) Uani 1 1 d . . .
C102 C 0.1500(2) 0.5056(3) 0.70371(13) 0.0320(7) Uani 1 1 d . . .
H10A H 0.1645 0.4889 0.7518 0.038 Uiso 1 1 calc R . .
C103 C 0.09317(18) 0.6086(2) 0.68326(12) 0.0226(6) Uani 1 1 d . . .
C105 C 0.13935(17) 0.5945(2) 0.56572(12) 0.0187(5) Uani 1 1 d . . .
C106 C 0.2873(2) 0.3604(3) 0.67799(15) 0.0468(9) Uani 1 1 d . . .
H10B H 0.3303 0.4365 0.6903 0.070 Uiso 1 1 calc R . .
H10C H 0.3121 0.3054 0.6416 0.070 Uiso 1 1 calc R . .
H10D H 0.2817 0.3035 0.7190 0.070 Uiso 1 1 calc R . .
C107 C 0.1231(2) 0.2964(3) 0.63242(15) 0.0421(8) Uani 1 1 d . . .
H10E H 0.0612 0.3330 0.6151 0.063 Uiso 1 1 calc R . .
H10F H 0.1167 0.2399 0.6734 0.063 Uiso 1 1 calc R . .
H10G H 0.1481 0.2409 0.5963 0.063 Uiso 1 1 calc R . .
C108 C 0.0414(2) 0.6904(3) 0.73169(13) 0.0368(7) Uani 1 1 d . . .
H10H H 0.0523 0.6519 0.7784 0.055 Uiso 1 1 calc R . .
H10I H -0.0264 0.6884 0.7165 0.055 Uiso 1 1 calc R . .
H10J H 0.0640 0.7848 0.7321 0.055 Uiso 1 1 calc R . .
C109 C 0.01368(17) 0.7502(2) 0.58993(12) 0.0183(5) Uani 1 1 d . . .
C110 C -0.07872(18) 0.7160(3) 0.56783(12) 0.0232(6) Uani 1 1 d . . .
H11A H -0.0963 0.6228 0.5626 0.028 Uiso 1 1 calc R . .
C111 C -0.14590(19) 0.8173(3) 0.55318(13) 0.0263(6) Uani 1 1 d . . .
H11B H -0.2095 0.7934 0.5387 0.032 Uiso 1 1 calc R . .
C112 C -0.12005(18) 0.9536(3) 0.55968(13) 0.0265(6) Uani 1 1 d . . .
H11C H -0.1663 1.0228 0.5501 0.032 Uiso 1 1 calc R . .
C113 C -0.02759(18) 0.9891(3) 0.58002(12) 0.0248(6) Uani 1 1 d . . .
H11D H -0.0096 1.0823 0.5837 0.030 Uiso 1 1 calc R . .
C114 C 0.03867(17) 0.8870(2) 0.59502(12) 0.0200(5) Uani 1 1 d . . .
S2 S 0.38343(5) 0.13848(6) 1.01405(3) 0.02269(16) Uani 1 1 d . . .
Cl2 Cl 0.34909(5) 0.43540(7) 0.86261(4) 0.03295(18) Uani 1 1 d . . .
N21 N 0.32218(15) -0.0075(2) 0.90440(10) 0.0236(5) Uani 1 1 d . . .
H2A H 0.2969 -0.0586 0.9350 0.028 Uiso 1 1 calc R . .
N22 N 0.43293(15) 0.1563(2) 0.88445(10) 0.0224(5) Uani 1 1 d . . .
C201 C 0.29746(19) -0.0423(3) 0.83114(13) 0.0273(6) Uani 1 1 d . . .
C202 C 0.3725(2) 0.0149(3) 0.79082(15) 0.0424(8) Uani 1 1 d . . .
H20A H 0.3767 -0.0185 0.7452 0.051 Uiso 1 1 calc R . .
C203 C 0.4337(2) 0.1096(3) 0.81499(13) 0.0284(6) Uani 1 1 d . . .
C205 C 0.37844(17) 0.0926(2) 0.92950(12) 0.0196(5) Uani 1 1 d . . .
C206 C 0.2871(2) -0.1940(3) 0.82409(16) 0.0445(8) Uani 1 1 d . . .
H20B H 0.3476 -0.2379 0.8390 0.067 Uiso 1 1 calc R . .
H20C H 0.2683 -0.2172 0.7756 0.067 Uiso 1 1 calc R . .
H20D H 0.2388 -0.2260 0.8530 0.067 Uiso 1 1 calc R . .
C207 C 0.2024(2) 0.0280(3) 0.80768(14) 0.0470(9) Uani 1 1 d . . .
H20E H 0.2095 0.1270 0.8127 0.071 Uiso 1 1 calc R . .
H20F H 0.1538 -0.0042 0.8364 0.071 Uiso 1 1 calc R . .
H20G H 0.1836 0.0057 0.7590 0.071 Uiso 1 1 calc R . .
C208 C 0.5027(2) 0.1739(3) 0.77270(14) 0.0417(8) Uani 1 1 d . . .
H20H H 0.4977 0.1319 0.7266 0.063 Uiso 1 1 calc R . .
H20I H 0.5667 0.1608 0.7953 0.063 Uiso 1 1 calc R . .
H20J H 0.4892 0.2717 0.7681 0.063 Uiso 1 1 calc R . .
C209 C 0.49313(18) 0.2676(2) 0.90839(12) 0.0206(6) Uani 1 1 d . . .
C210 C 0.58341(18) 0.2425(3) 0.93887(13) 0.0265(6) Uani 1 1 d . . .
H21A H 0.6043 0.1513 0.9466 0.032 Uiso 1 1 calc R . .
C211 C 0.64340(19) 0.3500(3) 0.95816(14) 0.0303(7) Uani 1 1 d . . .
H21B H 0.7053 0.3320 0.9793 0.036 Uiso 1 1 calc R . .
C212 C 0.61410(18) 0.4831(3) 0.94700(13) 0.0276(6) Uani 1 1 d . . .
H21C H 0.6562 0.5562 0.9597 0.033 Uiso 1 1 calc R . .
C213 C 0.52354(18) 0.5105(3) 0.91741(12) 0.0240(6) Uani 1 1 d . . .
H21D H 0.5026 0.6019 0.9102 0.029 Uiso 1 1 calc R . .
C214 C 0.46361(17) 0.4016(2) 0.89841(12) 0.0205(6) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C105 1.694(2) . ?
Cl1 C114 1.737(3) . ?
N11 C105 1.331(3) . ?
N11 C101 1.472(3) . ?
N12 C105 1.373(3) . ?
N12 C103 1.429(3) . ?
N12 C109 1.434(3) . ?
C101 C102 1.500(3) . ?
C101 C106 1.503(4) . ?
C101 C107 1.541(4) . ?
C102 C103 1.330(4) . ?
C103 C108 1.483(3) . ?
C109 C110 1.383(3) . ?
C109 C114 1.389(3) . ?
C110 C111 1.388(3) . ?
C111 C112 1.388(3) . ?
C112 C113 1.380(3) . ?
C113 C114 1.386(3) . ?
S2 C205 1.695(2) . ?
Cl2 C214 1.739(3) . ?
N21 C205 1.328(3) . ?
N21 C201 1.470(3) . ?
N22 C205 1.373(3) . ?
N22 C203 1.424(3) . ?
N22 C209 1.436(3) . ?
C201 C202 1.491(4) . ?
C201 C206 1.499(3) . ?
C201 C207 1.545(4) . ?
C202 C203 1.326(4) . ?
C203 C208 1.479(4) . ?
C209 C210 1.382(4) . ?
C209 C214 1.386(3) . ?
C210 C211 1.384(4) . ?
C211 C212 1.381(4) . ?
C212 C213 1.384(3) . ?
C213 C214 1.393(3) . ?

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
C105 N11 C101 125.3(2) . . ?
C105 N12 C103 120.7(2) . . ?
C105 N12 C109 119.81(19) . . ?
C103 N12 C109 118.89(19) . . ?
N11 C101 C102 107.2(2) . . ?
N11 C101 C106 109.4(2) . . ?
C102 C101 C106 113.0(2) . . ?
N11 C101 C107 107.7(2) . . ?
C102 C101 C107 109.4(2) . . ?
C106 C101 C107 110.0(2) . . ?
C103 C102 C101 121.1(2) . . ?
C102 C103 N12 119.8(2) . . ?
C102 C103 C108 123.1(2) . . ?
N12 C103 C108 117.1(2) . . ?
N11 C105 N12 116.6(2) . . ?
N11 C105 S1 121.53(18) . . ?
N12 C105 S1 121.89(18) . . ?
C110 C109 C114 119.0(2) . . ?
C110 C109 N12 119.9(2) . . ?
C114 C109 N12 121.0(2) . . ?
C109 C110 C111 120.3(2) . . ?
C110 C111 C112 119.9(2) . . ?
C113 C112 C111 120.3(2) . . ?
C112 C113 C114 119.2(2) . . ?
C113 C114 C109 121.2(2) . . ?
C113 C114 Cl1 119.84(19) . . ?
C109 C114 Cl1 118.92(19) . . ?
C205 N21 C201 127.2(2) . . ?
C205 N22 C203 120.8(2) . . ?
C205 N22 C209 119.7(2) . . ?
C203 N22 C209 119.5(2) . . ?
N21 C201 C202 107.7(2) . . ?
N21 C201 C206 109.3(2) . . ?
C202 C201 C206 113.2(2) . . ?
N21 C201 C207 107.5(2) . . ?
C202 C201 C207 109.1(2) . . ?
C206 C201 C207 109.9(3) . . ?
C203 C202 C201 123.7(3) . . ?
C202 C203 N22 119.7(2) . . ?
C202 C203 C208 123.3(2) . . ?
N22 C203 C208 117.0(2) . . ?
N21 C205 N22 117.4(2) . . ?
N21 C205 S2 121.19(18) . . ?
N22 C205 S2 121.45(18) . . ?
C210 C209 C214 119.0(2) . . ?
C210 C209 N22 120.2(2) . . ?
C214 C209 N22 120.8(2) . . ?
C209 C210 C211 120.2(2) . . ?
C212 C211 C210 120.6(3) . . ?
C211 C212 C213 120.2(2) . . ?
C212 C213 C214 118.8(2) . . ?
C209 C214 C213 121.3(2) . . ?
C209 C214 Cl2 119.70(19) . . ?
C213 C214 Cl2 118.97(19) . . ?

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
C105 N11 C101 C102 -34.2(3) . . . . ?
C105 N11 C101 C106 -157.0(2) . . . . ?
C105 N11 C101 C107 83.4(3) . . . . ?
N11 C101 C102 C103 28.1(4) . . . . ?
C106 C101 C102 C103 148.7(3) . . . . ?
C107 C101 C102 C103 -88.5(3) . . . . ?
C101 C102 C103 N12 -7.8(4) . . . . ?
C101 C102 C103 C108 172.5(3) . . . . ?
C105 N12 C103 C102 -13.1(4) . . . . ?
C109 N12 C103 C102 175.6(2) . . . . ?
C105 N12 C103 C108 166.6(2) . . . . ?
C109 N12 C103 C108 -4.7(3) . . . . ?
C101 N11 C105 N12 17.2(3) . . . . ?
C101 N11 C105 S1 -163.76(19) . . . . ?
C103 N12 C105 N11 8.8(3) . . . . ?
C109 N12 C105 N11 180.0(2) . . . . ?
C103 N12 C105 S1 -170.26(18) . . . . ?
C109 N12 C105 S1 1.0(3) . . . . ?
C105 N12 C109 C110 96.5(3) . . . . ?
C103 N12 C109 C110 -92.1(3) . . . . ?
C105 N12 C109 C114 -87.8(3) . . . . ?
C103 N12 C109 C114 83.6(3) . . . . ?
C114 C109 C110 C111 -2.1(4) . . . . ?
N12 C109 C110 C111 173.7(2) . . . . ?
C109 C110 C111 C112 1.0(4) . . . . ?
C110 C111 C112 C113 0.6(4) . . . . ?
C111 C112 C113 C114 -1.1(4) . . . . ?
C112 C113 C114 C109 0.0(4) . . . . ?
C112 C113 C114 Cl1 179.44(18) . . . . ?
C110 C109 C114 C113 1.6(4) . . . . ?
N12 C109 C114 C113 -174.2(2) . . . . ?
C110 C109 C114 Cl1 -177.85(18) . . . . ?
N12 C109 C114 Cl1 6.4(3) . . . . ?
C205 N21 C201 C202 21.8(4) . . . . ?
C205 N21 C201 C206 145.1(3) . . . . ?
C205 N21 C201 C207 -95.7(3) . . . . ?
N21 C201 C202 C203 -16.6(4) . . . . ?
C206 C201 C202 C203 -137.4(3) . . . . ?
C207 C201 C202 C203 99.9(3) . . . . ?
C201 C202 C203 N22 3.6(5) . . . . ?
C201 C202 C203 C208 -174.7(3) . . . . ?
C205 N22 C203 C202 8.6(4) . . . . ?
C209 N22 C203 C202 -174.2(3) . . . . ?
C205 N22 C203 C208 -173.1(2) . . . . ?
C209 N22 C203 C208 4.2(4) . . . . ?
C201 N21 C205 N22 -12.5(4) . . . . ?
C201 N21 C205 S2 168.2(2) . . . . ?
C203 N22 C205 N21 -4.5(3) . . . . ?
C209 N22 C205 N21 178.3(2) . . . . ?
C203 N22 C205 S2 174.91(19) . . . . ?
C209 N22 C205 S2 -2.3(3) . . . . ?
C205 N22 C209 C210 86.6(3) . . . . ?
C203 N22 C209 C210 -90.6(3) . . . . ?
C205 N22 C209 C214 -96.5(3) . . . . ?
C203 N22 C209 C214 86.2(3) . . . . ?
C214 C209 C210 C211 -0.8(4) . . . . ?
N22 C209 C210 C211 176.1(2) . . . . ?
C209 C210 C211 C212 -0.3(4) . . . . ?
C210 C211 C212 C213 1.2(4) . . . . ?
C211 C212 C213 C214 -0.9(4) . . . . ?
C210 C209 C214 C213 1.1(4) . . . . ?
N22 C209 C214 C213 -175.9(2) . . . . ?
C210 C209 C214 Cl2 -178.03(18) . . . . ?
N22 C209 C214 Cl2 5.1(3) . . . . ?
C212 C213 C214 C209 -0.2(4) . . . . ?
C212 C213 C214 Cl2 178.90(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.87
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.569
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.070
####################################################################### 
# 
# 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_s2408
_database_code_depnum_ccdc_archive 'CCDC 1504148'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H20 N2 S'
_chemical_formula_weight         260.39

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

loop_
_symmetry_equiv_pos_as_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                   12.228(3)
_cell_length_b                   8.896(2)
_cell_length_c                   14.798(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.166(6)
_cell_angle_gamma                90.00
_cell_volume                     1480.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    789
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      18.65

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.9264
_exptl_absorpt_correction_T_max  0.9939

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13456
_diffrn_reflns_av_R_equivalents  0.0998
_diffrn_reflns_av_sigmaI/netI    0.1608
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3524
_reflns_number_gt                1481
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0284P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3524
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1389
_refine_ls_R_factor_gt           0.0544
_refine_ls_wR_factor_ref         0.1042
_refine_ls_wR_factor_gt          0.0865
_refine_ls_goodness_of_fit_ref   0.765
_refine_ls_restrained_S_all      0.765
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.61475(7) 0.80615(9) 1.02030(5) 0.0437(2) Uani 1 1 d . . .
N1 N 0.45479(19) 0.9200(3) 0.85716(14) 0.0362(6) Uani 1 1 d . . .
H1A H 0.4369 0.9776 0.8977 0.043 Uiso 1 1 calc R . .
N2 N 0.54385(17) 0.7020(2) 0.83747(13) 0.0291(5) Uani 1 1 d . . .
C1 C 0.5326(2) 0.8110(3) 0.89809(17) 0.0297(6) Uani 1 1 d . . .
C2 C 0.3952(2) 0.9556(3) 0.75240(18) 0.0298(7) Uani 1 1 d . . .
C3 C 0.4599(3) 1.0890(4) 0.7318(2) 0.0692(11) Uani 1 1 d . . .
H3A H 0.4500 1.1772 0.7675 0.104 Uiso 1 1 calc R . .
H3B H 0.4265 1.1102 0.6611 0.104 Uiso 1 1 calc R . .
H3C H 0.5446 1.0654 0.7535 0.104 Uiso 1 1 calc R . .
C4 C 0.2669(3) 0.9942(4) 0.7295(2) 0.0656(11) Uani 1 1 d . . .
H4A H 0.2278 0.9086 0.7461 0.098 Uiso 1 1 calc R . .
H4B H 0.2263 1.0169 0.6593 0.098 Uiso 1 1 calc R . .
H4C H 0.2631 1.0820 0.7681 0.098 Uiso 1 1 calc R . .
C5 C 0.4041(2) 0.8220(3) 0.69483(18) 0.0369(7) Uani 1 1 d . . .
H5A H 0.3583 0.8213 0.6260 0.044 Uiso 1 1 calc R . .
C6 C 0.4722(2) 0.7045(3) 0.73425(17) 0.0302(7) Uani 1 1 d . . .
C7 C 0.4753(2) 0.5671(3) 0.67784(18) 0.0446(8) Uani 1 1 d . . .
H7A H 0.4216 0.5801 0.6088 0.067 Uiso 1 1 calc R . .
H7B H 0.4497 0.4802 0.7053 0.067 Uiso 1 1 calc R . .
H7C H 0.5565 0.5506 0.6823 0.067 Uiso 1 1 calc R . .
C8 C 0.6282(2) 0.5816(3) 0.87757(17) 0.0310(7) Uani 1 1 d . . .
C9 C 0.5928(3) 0.4532(3) 0.91169(18) 0.0376(8) Uani 1 1 d . . .
H9A H 0.5157 0.4472 0.9126 0.045 Uiso 1 1 calc R . .
C10 C 0.6717(3) 0.3329(3) 0.94476(19) 0.0485(9) Uani 1 1 d . . .
H10A H 0.6482 0.2445 0.9684 0.058 Uiso 1 1 calc R . .
C11 C 0.7838(3) 0.3418(4) 0.9433(2) 0.0480(9) Uani 1 1 d . . .
C12 C 0.8170(3) 0.4721(4) 0.91020(19) 0.0467(9) Uani 1 1 d . . .
H12A H 0.8945 0.4782 0.9101 0.056 Uiso 1 1 calc R . .
C13 C 0.7411(2) 0.5949(3) 0.87691(18) 0.0345(7) Uani 1 1 d . . .
C14 C 0.7789(2) 0.7369(3) 0.8420(2) 0.0523(9) Uani 1 1 d . . .
H14A H 0.8605 0.7255 0.8463 0.078 Uiso 1 1 calc R . .
H14B H 0.7752 0.8213 0.8832 0.078 Uiso 1 1 calc R . .
H14C H 0.7255 0.7563 0.7736 0.078 Uiso 1 1 calc R . .
C15 C 0.8670(3) 0.2072(4) 0.9765(2) 0.0771(12) Uani 1 1 d . . .
H15A H 0.8341 0.1236 0.9306 0.116 Uiso 1 1 calc R . .
H15B H 0.8752 0.1766 1.0425 0.116 Uiso 1 1 calc R . .
H15C H 0.9452 0.2346 0.9778 0.116 Uiso 1 1 calc R . .


_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 C1 1.689(2) . ?
N1 C1 1.326(3) . ?
N1 C2 1.465(3) . ?
N2 C1 1.364(3) . ?
N2 C6 1.431(3) . ?
N2 C8 1.443(3) . ?
C2 C5 1.491(3) . ?
C2 C4 1.509(3) . ?
C2 C3 1.521(4) . ?
C5 C6 1.321(3) . ?
C6 C7 1.489(3) . ?
C8 C9 1.385(4) . ?
C8 C13 1.390(3) . ?
C9 C10 1.394(4) . ?
C10 C11 1.383(4) . ?
C11 C12 1.380(4) . ?
C11 C15 1.522(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.505(4) . ?

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
C1 N1 C2 127.6(2) . . ?
C1 N2 C6 120.9(2) . . ?
C1 N2 C8 119.9(2) . . ?
C6 N2 C8 119.3(2) . . ?
N1 C1 N2 117.3(2) . . ?
N1 C1 S1 121.7(2) . . ?
N2 C1 S1 121.0(2) . . ?
N1 C2 C5 108.3(2) . . ?
N1 C2 C4 109.1(2) . . ?
C5 C2 C4 110.9(2) . . ?
N1 C2 C3 107.4(2) . . ?
C5 C2 C3 110.3(2) . . ?
C4 C2 C3 110.7(3) . . ?
C6 C5 C2 123.6(2) . . ?
C5 C6 N2 119.9(2) . . ?
C5 C6 C7 123.5(2) . . ?
N2 C6 C7 116.5(2) . . ?
C9 C8 C13 121.7(3) . . ?
C9 C8 N2 119.2(3) . . ?
C13 C8 N2 119.0(3) . . ?
C8 C9 C10 119.3(3) . . ?
C11 C10 C9 120.3(3) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 C15 121.5(3) . . ?
C10 C11 C15 119.4(3) . . ?
C11 C12 C13 122.4(3) . . ?
C8 C13 C12 117.2(3) . . ?
C8 C13 C14 120.9(3) . . ?
C12 C13 C14 121.9(3) . . ?

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
C2 N1 C1 N2 -13.1(4) . . . . ?
C2 N1 C1 S1 167.0(2) . . . . ?
C6 N2 C1 N1 -1.3(4) . . . . ?
C8 N2 C1 N1 179.2(2) . . . . ?
C6 N2 C1 S1 178.60(19) . . . . ?
C8 N2 C1 S1 -0.9(3) . . . . ?
C1 N1 C2 C5 18.2(4) . . . . ?
C1 N1 C2 C4 139.0(3) . . . . ?
C1 N1 C2 C3 -100.9(3) . . . . ?
N1 C2 C5 C6 -10.5(4) . . . . ?
C4 C2 C5 C6 -130.1(3) . . . . ?
C3 C2 C5 C6 106.8(3) . . . . ?
C2 C5 C6 N2 -0.8(4) . . . . ?
C2 C5 C6 C7 176.0(2) . . . . ?
C1 N2 C6 C5 7.8(4) . . . . ?
C8 N2 C6 C5 -172.7(3) . . . . ?
C1 N2 C6 C7 -169.2(2) . . . . ?
C8 N2 C6 C7 10.3(4) . . . . ?
C1 N2 C8 C9 88.3(3) . . . . ?
C6 N2 C8 C9 -91.2(3) . . . . ?
C1 N2 C8 C13 -94.6(3) . . . . ?
C6 N2 C8 C13 86.0(3) . . . . ?
C13 C8 C9 C10 -1.1(4) . . . . ?
N2 C8 C9 C10 176.0(2) . . . . ?
C8 C9 C10 C11 -0.1(4) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C9 C10 C11 C15 -177.9(2) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C15 C11 C12 C13 178.1(3) . . . . ?
C9 C8 C13 C12 1.3(4) . . . . ?
N2 C8 C13 C12 -175.8(2) . . . . ?
C9 C8 C13 C14 -178.4(2) . . . . ?
N2 C8 C13 C14 4.5(4) . . . . ?
C11 C12 C13 C8 -0.3(4) . . . . ?
C11 C12 C13 C14 179.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.049
####################################################################### 
# 
# 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_s2423
_database_code_depnum_ccdc_archive 'CCDC 1504147'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H14 Cl2 N2 S'
_chemical_formula_weight         301.22

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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.072(4)
_cell_length_b                   7.010(2)
_cell_length_c                   17.035(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.402(7)
_cell_angle_gamma                90.00
_cell_volume                     1413.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    969
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      20.17

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.590
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.8762
_exptl_absorpt_correction_T_max  0.9768

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12844
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_sigmaI/netI    0.0873
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.72
_diffrn_reflns_theta_max         27.88
_reflns_number_total             3377
_reflns_number_gt                2142
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.0936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3377
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1259
_refine_ls_wR_factor_gt          0.1075
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.06393(6) 0.29607(12) 0.18322(4) 0.0236(2) Uani 1 1 d . . .
Cl1 Cl 0.39517(7) 0.28258(12) 0.21605(5) 0.0333(2) Uani 1 1 d . . .
Cl2 Cl 0.46506(7) 0.55981(14) 0.08813(5) 0.0365(2) Uani 1 1 d . . .
N1 N 0.1140(2) 0.1939(4) 0.33528(14) 0.0265(6) Uani 1 1 d . . .
H1A H 0.0697 0.0961 0.3190 0.032 Uiso 1 1 calc R . .
N2 N 0.2221(2) 0.4392(4) 0.30107(14) 0.0224(6) Uani 1 1 d . . .
C1 C 0.1554(3) 0.2121(5) 0.42238(18) 0.0293(8) Uani 1 1 d . . .
C2 C 0.0668(4) 0.3185(8) 0.4562(2) 0.0700(15) Uani 1 1 d . . .
H2A H 0.0563 0.4457 0.4321 0.105 Uiso 1 1 calc R . .
H2B H 0.0915 0.3306 0.5144 0.105 Uiso 1 1 calc R . .
H2C H -0.0047 0.2482 0.4442 0.105 Uiso 1 1 calc R . .
C3 C 0.1713(4) 0.0157(6) 0.4595(2) 0.0638(14) Uani 1 1 d . . .
H3A H 0.2291 -0.0533 0.4377 0.096 Uiso 1 1 calc R . .
H3B H 0.0998 -0.0545 0.4471 0.096 Uiso 1 1 calc R . .
H3C H 0.1954 0.0276 0.5177 0.096 Uiso 1 1 calc R . .
C4 C 0.2633(3) 0.3191(6) 0.4346(2) 0.0446(10) Uani 1 1 d . . .
H4A H 0.3166 0.3003 0.4831 0.054 Uiso 1 1 calc R . .
C5 C 0.2891(3) 0.4413(5) 0.38033(19) 0.0296(8) Uani 1 1 d . . .
C6 C 0.3853(3) 0.5688(6) 0.3956(2) 0.0434(10) Uani 1 1 d . . .
H6A H 0.4185 0.5683 0.4530 0.065 Uiso 1 1 calc R . .
H6B H 0.3607 0.6983 0.3789 0.065 Uiso 1 1 calc R . .
H6C H 0.4418 0.5260 0.3653 0.065 Uiso 1 1 calc R . .
C7 C 0.1366(2) 0.3094(4) 0.27886(17) 0.0209(7) Uani 1 1 d . . .
C8 C 0.2517(2) 0.5618(4) 0.24094(17) 0.0209(7) Uani 1 1 d . . .
C9 C 0.2020(3) 0.7384(4) 0.22686(19) 0.0264(7) Uani 1 1 d . . .
H9A H 0.1467 0.7777 0.2561 0.032 Uiso 1 1 calc R . .
C10 C 0.2321(3) 0.8588(5) 0.1705(2) 0.0310(8) Uani 1 1 d . . .
H10A H 0.1969 0.9801 0.1608 0.037 Uiso 1 1 calc R . .
C11 C 0.3131(3) 0.8040(5) 0.12787(19) 0.0277(7) Uani 1 1 d . . .
H11A H 0.3335 0.8871 0.0890 0.033 Uiso 1 1 calc R . .
C12 C 0.3640(2) 0.6276(5) 0.14216(17) 0.0236(7) Uani 1 1 d . . .
C13 C 0.3337(3) 0.5036(4) 0.19848(18) 0.0233(7) Uani 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.694(3) . ?
Cl1 C13 1.718(3) . ?
Cl2 C12 1.734(3) . ?
N1 C7 1.326(4) . ?
N1 C1 1.474(4) . ?
N2 C7 1.371(4) . ?
N2 C5 1.430(4) . ?
N2 C8 1.436(4) . ?
C1 C4 1.482(5) . ?
C1 C2 1.508(5) . ?
C1 C3 1.511(5) . ?
C4 C5 1.342(5) . ?
C5 C6 1.447(5) . ?
C8 C9 1.376(4) . ?
C8 C13 1.397(4) . ?
C9 C10 1.380(5) . ?
C10 C11 1.382(4) . ?
C11 C12 1.381(4) . ?
C12 C13 1.396(4) . ?

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 126.8(3) . . ?
C7 N2 C5 121.4(3) . . ?
C7 N2 C8 118.7(2) . . ?
C5 N2 C8 119.5(2) . . ?
N1 C1 C4 107.4(3) . . ?
N1 C1 C2 107.6(3) . . ?
C4 C1 C2 111.4(3) . . ?
N1 C1 C3 109.4(3) . . ?
C4 C1 C3 111.5(3) . . ?
C2 C1 C3 109.4(3) . . ?
C5 C4 C1 122.9(3) . . ?
C4 C5 N2 118.6(3) . . ?
C4 C5 C6 123.9(3) . . ?
N2 C5 C6 117.4(3) . . ?
N1 C7 N2 117.2(3) . . ?
N1 C7 S1 121.4(2) . . ?
N2 C7 S1 121.4(2) . . ?
C9 C8 C13 120.1(3) . . ?
C9 C8 N2 120.1(3) . . ?
C13 C8 N2 119.8(3) . . ?
C8 C9 C10 120.4(3) . . ?
C9 C10 C11 120.4(3) . . ?
C12 C11 C10 119.5(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 Cl2 119.2(2) . . ?
C13 C12 Cl2 120.1(3) . . ?
C12 C13 C8 118.8(3) . . ?
C12 C13 Cl1 121.2(2) . . ?
C8 C13 Cl1 119.9(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 C1 C4 -25.8(4) . . . . ?
C7 N1 C1 C2 94.2(4) . . . . ?
C7 N1 C1 C3 -147.0(3) . . . . ?
N1 C1 C4 C5 25.6(5) . . . . ?
C2 C1 C4 C5 -92.0(5) . . . . ?
C3 C1 C4 C5 145.4(4) . . . . ?
C1 C4 C5 N2 -13.6(6) . . . . ?
C1 C4 C5 C6 170.1(4) . . . . ?
C7 N2 C5 C4 -3.3(5) . . . . ?
C8 N2 C5 C4 -176.8(3) . . . . ?
C7 N2 C5 C6 173.2(3) . . . . ?
C8 N2 C5 C6 -0.3(4) . . . . ?
C1 N1 C7 N2 12.5(5) . . . . ?
C1 N1 C7 S1 -168.1(2) . . . . ?
C5 N2 C7 N1 4.2(4) . . . . ?
C8 N2 C7 N1 177.7(3) . . . . ?
C5 N2 C7 S1 -175.3(2) . . . . ?
C8 N2 C7 S1 -1.8(4) . . . . ?
C7 N2 C8 C9 92.3(3) . . . . ?
C5 N2 C8 C9 -94.1(3) . . . . ?
C7 N2 C8 C13 -89.7(3) . . . . ?
C5 N2 C8 C13 83.9(4) . . . . ?
C13 C8 C9 C10 0.4(5) . . . . ?
N2 C8 C9 C10 178.5(3) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C13 0.7(5) . . . . ?
C10 C11 C12 Cl2 179.7(2) . . . . ?
C11 C12 C13 C8 -0.7(4) . . . . ?
Cl2 C12 C13 C8 -179.8(2) . . . . ?
C11 C12 C13 Cl1 179.3(2) . . . . ?
Cl2 C12 C13 Cl1 0.2(4) . . . . ?
C9 C8 C13 C12 0.2(4) . . . . ?
N2 C8 C13 C12 -177.9(3) . . . . ?
C9 C8 C13 Cl1 -179.8(2) . . . . ?
N2 C8 C13 Cl1 2.2(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.563
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_s2365
_database_code_depnum_ccdc_archive 'CCDC 1504149'
_audit_update_record             
;
2016-09-13 deposited with the CCDC.
2017-02-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H18 N2 O S'
_chemical_formula_weight         262.36

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.729(3)
_cell_length_b                   9.683(3)
_cell_length_c                   10.503(4)
_cell_angle_alpha                64.578(5)
_cell_angle_beta                 78.685(6)
_cell_angle_gamma                63.892(6)
_cell_volume                     719.9(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    762
_cell_measurement_theta_min      2.54
_cell_measurement_theta_max      25.41

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2004)'
_exptl_absorpt_correction_T_min  0.9036
_exptl_absorpt_correction_T_max  0.9914

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker AXS SMART APEX'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5079
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_sigmaI/netI    0.1211
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.15
_diffrn_reflns_theta_max         27.10
_reflns_number_total             3133
_reflns_number_gt                1687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0257P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3133
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1080
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   0.824
_refine_ls_restrained_S_all      0.824
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.24012(9) 0.81042(8) 0.11180(7) 0.0379(2) Uani 1 1 d . . .
O1 O 0.8395(2) 0.1345(2) 0.39205(17) 0.0428(5) Uani 1 1 d . . .
N1 N 0.1569(3) 0.5485(3) 0.2528(2) 0.0394(6) Uani 1 1 d . . .
N2 N -0.0568(2) 0.7944(2) 0.1238(2) 0.0383(6) Uani 1 1 d . . .
H2 H -0.0894 0.9023 0.0738 0.046 Uiso 1 1 calc R . .
C1 C 0.3364(3) 0.4476(3) 0.2842(3) 0.0368(6) Uani 1 1 d . . .
C2 C 0.4418(4) 0.3823(3) 0.1912(3) 0.0441(7) Uani 1 1 d . . .
H2A H 0.3976 0.4096 0.1037 0.053 Uiso 1 1 calc R . .
C3 C 0.6119(3) 0.2770(3) 0.2220(3) 0.0422(7) Uani 1 1 d . . .
H3A H 0.6840 0.2317 0.1568 0.051 Uiso 1 1 calc R . .
C4 C 0.6747(3) 0.2389(3) 0.3494(3) 0.0359(6) Uani 1 1 d . . .
C5 C 0.5693(3) 0.3073(3) 0.4429(3) 0.0390(7) Uani 1 1 d . . .
H5A H 0.6131 0.2817 0.5299 0.047 Uiso 1 1 calc R . .
C6 C 0.4003(3) 0.4127(3) 0.4098(3) 0.0386(7) Uani 1 1 d . . .
H6A H 0.3283 0.4609 0.4733 0.046 Uiso 1 1 calc R . .
C7 C 0.9531(3) 0.0645(3) 0.2977(3) 0.0525(8) Uani 1 1 d . . .
H7A H 0.9100 -0.0024 0.2784 0.079 Uiso 1 1 calc R . .
H7B H 1.0662 -0.0066 0.3403 0.079 Uiso 1 1 calc R . .
H7C H 0.9613 0.1545 0.2093 0.079 Uiso 1 1 calc R . .
C8 C 0.0380(4) 0.4701(3) 0.3058(3) 0.0448(7) Uani 1 1 d . . .
C9 C -0.1222(3) 0.5561(3) 0.2600(3) 0.0500(8) Uani 1 1 d . . .
H9A H -0.1994 0.5031 0.3003 0.060 Uiso 1 1 calc R . .
C10 C -0.1891(3) 0.7282(3) 0.1508(3) 0.0398(7) Uani 1 1 d . . .
C11 C 0.1039(3) 0.7127(3) 0.1650(2) 0.0340(6) Uani 1 1 d . . .
C12 C 0.1023(4) 0.2961(4) 0.4119(3) 0.0767(11) Uani 1 1 d . . .
H12A H 0.0126 0.2539 0.4351 0.115 Uiso 1 1 calc R . .
H12B H 0.1347 0.2936 0.4973 0.115 Uiso 1 1 calc R . .
H12C H 0.2020 0.2258 0.3735 0.115 Uiso 1 1 calc R . .
C13 C -0.2251(4) 0.7285(4) 0.0142(3) 0.0632(9) Uani 1 1 d . . .
H13A H -0.2614 0.8423 -0.0583 0.095 Uiso 1 1 calc R . .
H13B H -0.3158 0.6888 0.0307 0.095 Uiso 1 1 calc R . .
H13C H -0.1213 0.6547 -0.0177 0.095 Uiso 1 1 calc R . .
C14 C -0.3518(3) 0.8431(3) 0.1992(3) 0.0512(8) Uani 1 1 d . . .
H14A H -0.3295 0.8450 0.2863 0.077 Uiso 1 1 calc R . .
H14B H -0.4414 0.8019 0.2168 0.077 Uiso 1 1 calc R . .
H14C H -0.3890 0.9563 0.1259 0.077 Uiso 1 1 calc R . .


_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 C11 1.702(3) . ?
O1 C4 1.369(3) . ?
O1 C7 1.423(3) . ?
N1 C11 1.362(3) . ?
N1 C8 1.438(3) . ?
N1 C1 1.448(3) . ?
N2 C11 1.322(3) . ?
N2 C10 1.481(3) . ?
C1 C2 1.366(3) . ?
C1 C6 1.380(3) . ?
C2 C3 1.386(3) . ?
C3 C4 1.384(3) . ?
C4 C5 1.384(3) . ?
C5 C6 1.382(3) . ?
C8 C9 1.333(3) . ?
C8 C12 1.482(3) . ?
C9 C10 1.483(3) . ?
C10 C14 1.525(3) . ?
C10 C13 1.527(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O1 C7 117.7(2) . . ?
C11 N1 C8 120.5(2) . . ?
C11 N1 C1 120.1(2) . . ?
C8 N1 C1 119.2(2) . . ?
C11 N2 C10 128.5(2) . . ?
C2 C1 C6 119.9(2) . . ?
C2 C1 N1 119.8(2) . . ?
C6 C1 N1 120.2(2) . . ?
C1 C2 C3 121.2(2) . . ?
C4 C3 C2 118.8(3) . . ?
O1 C4 C3 123.9(2) . . ?
O1 C4 C5 115.9(2) . . ?
C3 C4 C5 120.2(2) . . ?
C6 C5 C4 120.1(2) . . ?
C1 C6 C5 119.8(2) . . ?
C9 C8 N1 119.3(2) . . ?
C9 C8 C12 123.6(3) . . ?
N1 C8 C12 117.0(2) . . ?
C8 C9 C10 125.0(3) . . ?
N2 C10 C9 107.4(2) . . ?
N2 C10 C14 108.2(2) . . ?
C9 C10 C14 112.1(2) . . ?
N2 C10 C13 109.2(2) . . ?
C9 C10 C13 111.0(2) . . ?
C14 C10 C13 108.9(2) . . ?
N2 C11 N1 118.1(2) . . ?
N2 C11 S1 121.0(2) . . ?
N1 C11 S1 120.86(19) . . ?

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
C11 N1 C1 C2 -81.3(3) . . . . ?
C8 N1 C1 C2 93.6(3) . . . . ?
C11 N1 C1 C6 100.9(3) . . . . ?
C8 N1 C1 C6 -84.3(3) . . . . ?
C6 C1 C2 C3 1.8(4) . . . . ?
N1 C1 C2 C3 -176.0(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C7 O1 C4 C3 1.6(4) . . . . ?
C7 O1 C4 C5 -178.6(2) . . . . ?
C2 C3 C4 O1 178.9(2) . . . . ?
C2 C3 C4 C5 -0.9(4) . . . . ?
O1 C4 C5 C6 -179.2(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C2 C1 C6 C5 -2.1(4) . . . . ?
N1 C1 C6 C5 175.7(2) . . . . ?
C4 C5 C6 C1 0.9(4) . . . . ?
C11 N1 C8 C9 5.0(4) . . . . ?
C1 N1 C8 C9 -169.8(3) . . . . ?
C11 N1 C8 C12 -174.0(2) . . . . ?
C1 N1 C8 C12 11.2(4) . . . . ?
N1 C8 C9 C10 3.1(4) . . . . ?
C12 C8 C9 C10 -178.0(3) . . . . ?
C11 N2 C10 C9 11.9(4) . . . . ?
C11 N2 C10 C14 133.1(3) . . . . ?
C11 N2 C10 C13 -108.5(3) . . . . ?
C8 C9 C10 N2 -10.2(4) . . . . ?
C8 C9 C10 C14 -129.0(3) . . . . ?
C8 C9 C10 C13 109.0(3) . . . . ?
C10 N2 C11 N1 -5.6(4) . . . . ?
C10 N2 C11 S1 175.27(19) . . . . ?
C8 N1 C11 N2 -3.9(3) . . . . ?
C1 N1 C11 N2 170.9(2) . . . . ?
C8 N1 C11 S1 175.28(19) . . . . ?
C1 N1 C11 S1 -9.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.047
