# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1423371'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-11-13 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         'C19 H16 Cl N2 O3 P S'
_chemical_formula_sum            'C19 H16 Cl N2 O3 P S'
_chemical_formula_weight         418.82

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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   17.7272(3)
_cell_length_b                   10.9714(2)
_cell_length_c                   10.2468(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.6257(19)
_cell_angle_gamma                90
_cell_volume                     1975.29(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8855
_cell_measurement_theta_min      3.2460
_cell_measurement_theta_max      25.4660

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.43
_exptl_crystal_size_min          0.30
_exptl_absorpt_coefficient_mu    0.402
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92802
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11779
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.408
_diffrn_reflns_theta_max         25.542
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             3630
_reflns_number_gt                3357
_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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;







_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)+(0.0392P)²+1.7194P] 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         3630
_refine_ls_number_parameters     287
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.038
_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
P1 P 0.29310(3) 0.73491(4) 0.41708(4) 0.02436(14) Uani 1 1 d . . . . .
O2 O 0.25020(8) 0.77601(12) 0.52107(12) 0.0303(3) Uani 1 1 d . . . . .
O3 O 0.33905(7) 0.83899(12) 0.35534(13) 0.0301(3) Uani 1 1 d . . . . .
C4 C 0.31378(11) 0.96158(17) 0.34983(19) 0.0291(4) Uani 1 1 d . . . . .
C5 C 0.27182(13) 1.00207(19) 0.2359(2) 0.0380(5) Uani 1 1 d . . . . .
H5 H 0.2587 0.9483 0.1638 0.046 Uiso 1 1 calc R U . . .
C6 C 0.24902(14) 1.1225(2) 0.2282(3) 0.0472(6) Uani 1 1 d . . . . .
H6 H 0.2194 1.1519 0.1505 0.057 Uiso 1 1 calc R U . . .
C7 C 0.26881(14) 1.1997(2) 0.3318(3) 0.0495(6) Uani 1 1 d . . . . .
H7 H 0.2526 1.2823 0.3258 0.059 Uiso 1 1 calc R U . . .
C8 C 0.31205(15) 1.1588(2) 0.4445(3) 0.0517(6) Uani 1 1 d . . . . .
H8 H 0.3262 1.2135 0.5154 0.062 Uiso 1 1 calc R U . . .
C9 C 0.33541(13) 1.0362(2) 0.4555(2) 0.0424(5) Uani 1 1 d . . . . .
H9 H 0.3650 1.0064 0.5330 0.051 Uiso 1 1 calc R U . . .
O10 O 0.35761(7) 0.64471(12) 0.47553(13) 0.0307(3) Uani 1 1 d . . . . .
C11 C 0.4071(4) 0.5825(4) 0.4014(7) 0.0291(19) Uani 0.640(8) 1 d . . P A 1
C12 C 0.4746(2) 0.6356(3) 0.3854(5) 0.0409(11) Uani 0.640(8) 1 d . . P A 1
H12 H 0.4879 0.7136 0.4216 0.049 Uiso 0.640(8) 1 calc R U P A 1
C13 C 0.5233(3) 0.5727(4) 0.3149(6) 0.0528(13) Uani 0.640(8) 1 d . . P A 1
H13 H 0.5714 0.6065 0.3041 0.063 Uiso 0.640(8) 1 calc R U P A 1
C14 C 0.5025(4) 0.4624(7) 0.2609(7) 0.0537(18) Uani 0.640(8) 1 d . . P A 1
H14 H 0.5358 0.4212 0.2104 0.064 Uiso 0.640(8) 1 calc R U P A 1
C15 C 0.4337(2) 0.4090(4) 0.2783(5) 0.0463(12) Uani 0.640(8) 1 d . . P A 1
H15 H 0.4204 0.3310 0.2420 0.056 Uiso 0.640(8) 1 calc R U P A 1
C16 C 0.3845(2) 0.4711(4) 0.3492(5) 0.0384(10) Uani 0.640(8) 1 d . . P A 1
H16 H 0.3366 0.4375 0.3614 0.046 Uiso 0.640(8) 1 calc R U P A 1
C11B C 0.4003(5) 0.5795(5) 0.3916(9) 0.033(4) Uani 0.360(8) 1 d G U P A 2
C12B C 0.4449(5) 0.6322(5) 0.3049(9) 0.058(3) Uani 0.360(8) 1 d G U P A 2
H12B H 0.4423 0.7175 0.2892 0.070 Uiso 0.360(8) 1 calc R U P A 2
C13B C 0.4931(5) 0.5600(6) 0.2413(9) 0.069(3) Uani 0.360(8) 1 d G U P A 2
H13B H 0.5235 0.5961 0.1820 0.083 Uiso 0.360(8) 1 calc R U P A 2
C14B C 0.4968(5) 0.4352(6) 0.2643(11) 0.062(4) Uani 0.360(8) 1 d G U P A 2
H14B H 0.5298 0.3859 0.2207 0.075 Uiso 0.360(8) 1 calc R U P A 2
C15B C 0.4523(5) 0.3825(4) 0.3509(11) 0.073(3) Uani 0.360(8) 1 d G U P A 2
H15B H 0.4548 0.2972 0.3667 0.087 Uiso 0.360(8) 1 calc R U P A 2
C16B C 0.4041(4) 0.4547(5) 0.4146(9) 0.053(2) Uani 0.360(8) 1 d G U P A 2
H16B H 0.3736 0.4187 0.4738 0.064 Uiso 0.360(8) 1 calc R U P A 2
N17 N 0.24536(8) 0.67623(14) 0.28287(14) 0.0246(3) Uani 1 1 d . . . . .
H17 H 0.2541 0.7072 0.2070 0.030 Uiso 1 1 calc R U . . .
C18 C 0.19271(10) 0.58246(16) 0.27876(18) 0.0253(4) Uani 1 1 d . . . . .
S19 S 0.17594(3) 0.51013(5) 0.41446(5) 0.03377(15) Uani 1 1 d . . . . .
N20 N 0.15928(9) 0.55737(15) 0.15594(15) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.1726 0.6016 0.0911 0.035 Uiso 1 1 calc R U . . .
C21 C 0.10382(11) 0.46428(18) 0.12350(19) 0.0298(4) Uani 1 1 d . . . . .
C22 C 0.11547(13) 0.3778(2) 0.0301(2) 0.0442(5) Uani 1 1 d . . . . .
H22 H 0.1600 0.3802 -0.0121 0.053 Uiso 1 1 calc R U . . .
C23 C 0.06116(16) 0.2870(2) -0.0015(3) 0.0561(7) Uani 1 1 d . . . . .
H23 H 0.0689 0.2277 -0.0658 0.067 Uiso 1 1 calc R U . . .
C24 C -0.00322(15) 0.2820(2) 0.0587(3) 0.0533(7) Uani 1 1 d . . . . .
H24 H -0.0397 0.2192 0.0379 0.064 Uiso 1 1 calc R U . . .
C25 C -0.01379(12) 0.3701(2) 0.1502(2) 0.0428(5) Uani 1 1 d . . . . .
C26 C 0.03827(11) 0.46244(19) 0.1830(2) 0.0337(4) Uani 1 1 d . . . . .
H26 H 0.0292 0.5233 0.2450 0.040 Uiso 1 1 calc R U . . .
Cl27 Cl -0.09597(4) 0.36842(9) 0.22595(8) 0.0744(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4604(13) . ?
P1 O10 1.5698(13) . ?
P1 O3 1.5825(13) . ?
P1 N17 1.6471(15) . ?
O3 C4 1.416(2) . ?
C4 C9 1.371(3) . ?
C4 C5 1.372(3) . ?
C5 C6 1.381(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.366(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.374(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.407(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
O10 C11B 1.413(5) . ?
O10 C11 1.411(4) . ?
C11 C12 1.361(7) . ?
C11 C16 1.372(7) . ?
C12 C13 1.381(6) . ?
C12 H12 0.9500 . ?
C13 C14 1.361(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.385(6) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C11B C12B 1.3900 . ?
C11B C16B 1.3900 . ?
C12B C13B 1.3900 . ?
C12B H12B 0.9500 . ?
C13B C14B 1.3900 . ?
C13B H13B 0.9500 . ?
C14B C15B 1.3900 . ?
C14B H14B 0.9500 . ?
C15B C16B 1.3900 . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
N17 C18 1.386(2) . ?
N17 H17 0.8800 . ?
C18 N20 1.347(2) . ?
C18 S19 1.6616(18) . ?
N20 C21 1.426(2) . ?
N20 H20 0.8800 . ?
C21 C26 1.382(3) . ?
C21 C22 1.383(3) . ?
C22 C23 1.393(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.368(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.376(4) . ?
C24 H24 0.9500 . ?
C25 C26 1.382(3) . ?
C25 Cl27 1.740(2) . ?
C26 H26 0.9500 . ?

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 P1 O10 109.87(8) . . ?
O2 P1 O3 114.48(8) . . ?
O10 P1 O3 102.70(7) . . ?
O2 P1 N17 118.05(8) . . ?
O10 P1 N17 109.86(8) . . ?
O3 P1 N17 100.55(7) . . ?
C4 O3 P1 121.63(11) . . ?
C9 C4 C5 122.8(2) . . ?
C9 C4 O3 118.81(19) . . ?
C5 C4 O3 118.31(17) . . ?
C4 C5 C6 118.7(2) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C7 C6 C5 120.4(2) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.5(2) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C7 C8 C9 120.3(2) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 117.3(2) . . ?
C4 C9 H9 121.3 . . ?
C8 C9 H9 121.3 . . ?
C11B O10 P1 120.6(4) . . ?
C11 O10 P1 125.0(3) . . ?
C12 C11 C16 123.4(4) . . ?
C12 C11 O10 118.5(5) . . ?
C16 C11 O10 118.1(5) . . ?
C11 C12 C13 118.0(4) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 120.1(4) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C15 121.3(4) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C16 C15 C14 119.0(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C11 C16 C15 118.1(4) . . ?
C11 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C12B C11B C16B 120.0 . . ?
C12B C11B O10 125.0(4) . . ?
C16B C11B O10 114.4(4) . . ?
C11B C12B C13B 120.0 . . ?
C11B C12B H12B 120.0 . . ?
C13B C12B H12B 120.0 . . ?
C14B C13B C12B 120.0 . . ?
C14B C13B H13B 120.0 . . ?
C12B C13B H13B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C13B C14B H14B 120.0 . . ?
C15B C14B H14B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C14B C15B H15B 120.0 . . ?
C15B C16B C11B 120.0 . . ?
C15B C16B H16B 120.0 . . ?
C11B C16B H16B 120.0 . . ?
C18 N17 P1 125.79(12) . . ?
C18 N17 H17 117.1 . . ?
P1 N17 H17 117.1 . . ?
N20 C18 N17 113.03(16) . . ?
N20 C18 S19 125.39(14) . . ?
N17 C18 S19 121.57(13) . . ?
C18 N20 C21 124.65(16) . . ?
C18 N20 H20 117.7 . . ?
C21 N20 H20 117.7 . . ?
C26 C21 C22 120.45(19) . . ?
C26 C21 N20 120.12(18) . . ?
C22 C21 N20 119.42(18) . . ?
C21 C22 C23 119.3(2) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C24 C23 C22 121.1(2) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C25 118.4(2) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C26 122.3(2) . . ?
C24 C25 Cl27 119.63(18) . . ?
C26 C25 Cl27 118.10(19) . . ?
C21 C26 C25 118.5(2) . . ?
C21 C26 H26 120.8 . . ?
C25 C26 H26 120.8 . . ?

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
O2 P1 O3 C4 -29.57(17) . . . . ?
O10 P1 O3 C4 -148.61(14) . . . . ?
N17 P1 O3 C4 98.04(14) . . . . ?
P1 O3 C4 C9 87.5(2) . . . . ?
P1 O3 C4 C5 -95.76(19) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
O3 C4 C5 C6 -177.97(19) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
C5 C6 C7 C8 0.4(4) . . . . ?
C6 C7 C8 C9 -1.1(4) . . . . ?
C5 C4 C9 C8 0.7(3) . . . . ?
O3 C4 C9 C8 177.32(19) . . . . ?
C7 C8 C9 C4 0.5(4) . . . . ?
O2 P1 O10 C11B 171.3(4) . . . . ?
O3 P1 O10 C11B -66.4(4) . . . . ?
N17 P1 O10 C11B 39.9(4) . . . . ?
O2 P1 O10 C11 176.3(3) . . . . ?
O3 P1 O10 C11 -61.4(4) . . . . ?
N17 P1 O10 C11 44.9(4) . . . . ?
P1 O10 C11 C12 91.4(7) . . . . ?
P1 O10 C11 C16 -88.6(5) . . . . ?
C16 C11 C12 C13 -1.2(10) . . . . ?
O10 C11 C12 C13 178.7(4) . . . . ?
C11 C12 C13 C14 1.7(9) . . . . ?
C12 C13 C14 C15 -1.9(10) . . . . ?
C13 C14 C15 C16 1.7(10) . . . . ?
C12 C11 C16 C15 1.0(10) . . . . ?
O10 C11 C16 C15 -178.9(4) . . . . ?
C14 C15 C16 C11 -1.1(9) . . . . ?
P1 O10 C11B C12B 60.1(8) . . . . ?
P1 O10 C11B C16B -128.8(5) . . . . ?
C16B C11B C12B C13B 0.0 . . . . ?
O10 C11B C12B C13B 170.6(10) . . . . ?
C11B C12B C13B C14B 0.0 . . . . ?
C12B C13B C14B C15B 0.0 . . . . ?
C13B C14B C15B C16B 0.0 . . . . ?
C14B C15B C16B C11B 0.0 . . . . ?
C12B C11B C16B C15B 0.0 . . . . ?
O10 C11B C16B C15B -171.6(9) . . . . ?
O2 P1 N17 C18 -52.33(17) . . . . ?
O10 P1 N17 C18 74.68(16) . . . . ?
O3 P1 N17 C18 -177.55(14) . . . . ?
P1 N17 C18 N20 176.55(13) . . . . ?
P1 N17 C18 S19 -4.4(2) . . . . ?
N17 C18 N20 C21 179.16(16) . . . . ?
S19 C18 N20 C21 0.1(3) . . . . ?
C18 N20 C21 C26 55.5(3) . . . . ?
C18 N20 C21 C22 -125.9(2) . . . . ?
C26 C21 C22 C23 -1.4(3) . . . . ?
N20 C21 C22 C23 -179.9(2) . . . . ?
C21 C22 C23 C24 -0.2(4) . . . . ?
C22 C23 C24 C25 1.0(4) . . . . ?
C23 C24 C25 C26 -0.2(4) . . . . ?
C23 C24 C25 Cl27 178.59(19) . . . . ?
C22 C21 C26 C25 2.2(3) . . . . ?
N20 C21 C26 C25 -179.29(18) . . . . ?
C24 C25 C26 C21 -1.4(3) . . . . ?
Cl27 C25 C26 C21 179.83(16) . . . . ?

_refine_diff_density_max         0.556
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1423372'
_audit_update_record             
;
2015-11-04 deposited with the CCDC.
2015-11-13 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         'C6 H7 Cl N, C N S'
_chemical_formula_sum            'C7 H7 Cl N2 S'
_chemical_formula_weight         186.66

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   15.742(4)
_cell_length_b                   7.7102(9)
_cell_length_c                   7.0694(12)
_cell_angle_alpha                90
_cell_angle_beta                 99.36(2)
_cell_angle_gamma                90
_cell_volume                     846.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1473
_cell_measurement_theta_min      3.7140
_cell_measurement_theta_max      24.9900

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.630
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.57767
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '110 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5161
_diffrn_reflns_av_unetI/netI     0.0669
_diffrn_reflns_av_R_equivalents  0.0758
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.950
_diffrn_reflns_theta_max         25.239
_diffrn_reflns_theta_full        25.239
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             1523
_reflns_number_gt                1139
_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.

 During integration a small twin domain was ignored. 
 The twin domains were randomly orientated.
 Tests to take the twinning into account resulted in poorer
 results mainly as the minor twin domain was much weaker 
 diffracting and not to the full resolution. Less than 2% 
 of the reflections were fully overlapped. Only some low 
 resolution reflections might be affected, if not already
 rejected as outliers. 
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;




_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)+(0.0320P)²+11.7508P] 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         1523
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0928
_refine_ls_wR_factor_ref         0.2191
_refine_ls_wR_factor_gt          0.2066
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_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 0.88462(15) 0.1114(2) 0.5942(3) 0.0417(6) Uani 1 1 d . . . . .
C2 C 0.8495(5) 0.3279(9) 0.5665(11) 0.0298(18) Uani 1 1 d . . . . .
C3 C 0.9091(6) 0.4567(10) 0.6082(13) 0.036(2) Uani 1 1 d . . . . .
H3 H 0.9680 0.4308 0.6524 0.044 Uiso 1 1 calc R U . . .
C4 C 0.8805(6) 0.6271(10) 0.5840(13) 0.038(2) Uani 1 1 d . . . . .
H4 H 0.9203 0.7198 0.6127 0.046 Uiso 1 1 calc R U . . .
C5 C 0.7958(5) 0.6625(10) 0.5192(12) 0.0354(19) Uani 1 1 d . . . . .
H5 H 0.7773 0.7795 0.5007 0.043 Uiso 1 1 calc R U . . .
C6 C 0.7373(5) 0.5305(9) 0.4809(10) 0.0238(16) Uani 1 1 d . . . . .
C7 C 0.7642(5) 0.3573(9) 0.5041(10) 0.0254(16) Uani 1 1 d . . . . .
H7 H 0.7246 0.2642 0.4774 0.031 Uiso 1 1 calc R U . . .
N8 N 0.6477(4) 0.5663(7) 0.4116(9) 0.0291(15) Uani 1 1 d . . . . .
H8A H 0.6361 0.6792 0.4355 0.044 Uiso 1 1 calc R U . . .
H8B H 0.6143 0.4961 0.4725 0.044 Uiso 1 1 calc R U . . .
H8C H 0.6360 0.5464 0.2831 0.044 Uiso 1 1 calc R U . . .
S11 S 0.55849(14) 0.1676(2) 0.2187(3) 0.0293(5) Uani 1 1 d . . . . .
C12 C 0.5966(5) 0.0269(9) 0.3842(11) 0.0255(17) Uani 1 1 d . . . . .
N13 N 0.6249(5) -0.0719(8) 0.5060(10) 0.0349(16) 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
Cl1 C2 1.759(7) . ?
C2 C7 1.362(11) . ?
C2 C3 1.365(11) . ?
C3 C4 1.390(11) . ?
C3 H3 0.9500 . ?
C4 C5 1.365(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.370(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.403(10) . ?
C6 N8 1.443(9) . ?
C7 H7 0.9500 . ?
N8 H8A 0.9100 . ?
N8 H8B 0.9100 . ?
N8 H8C 0.9100 . ?
S11 C12 1.636(8) . ?
C12 N13 1.181(10) . ?

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 C2 C3 123.7(7) . . ?
C7 C2 Cl1 118.0(6) . . ?
C3 C2 Cl1 118.3(6) . . ?
C2 C3 C4 117.6(8) . . ?
C2 C3 H3 121.2 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 120.6(8) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 120.4(7) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C7 120.2(7) . . ?
C5 C6 N8 120.9(7) . . ?
C7 C6 N8 118.8(6) . . ?
C2 C7 C6 117.3(7) . . ?
C2 C7 H7 121.3 . . ?
C6 C7 H7 121.3 . . ?
C6 N8 H8A 109.5 . . ?
C6 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
C6 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
N13 C12 S11 178.6(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C2 C3 C4 -0.5(13) . . . . ?
Cl1 C2 C3 C4 179.4(6) . . . . ?
C2 C3 C4 C5 -0.4(13) . . . . ?
C3 C4 C5 C6 1.3(13) . . . . ?
C4 C5 C6 C7 -1.3(12) . . . . ?
C4 C5 C6 N8 -179.7(7) . . . . ?
C3 C2 C7 C6 0.5(12) . . . . ?
Cl1 C2 C7 C6 -179.4(5) . . . . ?
C5 C6 C7 C2 0.4(11) . . . . ?
N8 C6 C7 C2 178.9(6) . . . . ?

_refine_diff_density_max         0.971
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.142

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1423373'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-11-13 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         'C12 H10 O4 P, C6 H7 Cl N, 0.5(C6 H6)'
_chemical_formula_sum            'C21 H20 Cl N O4 P'
_chemical_formula_weight         416.80

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'
P P 0.1023 0.0942 '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                   6.7856(6)
_cell_length_b                   11.797(5)
_cell_length_c                   15.113(4)
_cell_angle_alpha                67.80(3)
_cell_angle_beta                 80.388(17)
_cell_angle_gamma                74.82(2)
_cell_volume                     1077.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    1212
_cell_measurement_theta_min      3.3230
_cell_measurement_theta_max      25.0950

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             434
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.77688
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?



_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'130 images, ΔΦ 2.0° '
' 47 images, ΔΦ 2.0° '
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12856
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         25.225
_diffrn_reflns_theta_full        25.225
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.959
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.959
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.959
_reflns_number_total             3723
_reflns_number_gt                3175
_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.

 Two datasets were measured on the same crystal, recombined
 in Crysalispro and scaling and absorpion correction was
 performed on the recombined data
;

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;


_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)+(0.0683P)²+0.5810P] 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         3723
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1417
_refine_ls_wR_factor_gt          0.1293
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_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
Cl1 Cl 1.19928(16) -0.00759(8) 0.82687(7) 0.0942(3) Uani 1 1 d . . . . .
C2 C 1.0074(4) 0.0777(3) 0.74778(18) 0.0572(6) Uani 1 1 d . . . . .
C3 C 0.8751(5) 0.0148(3) 0.7341(2) 0.0659(7) Uani 1 1 d . . . . .
H3 H 0.8864 -0.0708 0.7672 0.079 Uiso 1 1 calc R U . . .
C4 C 0.7255(5) 0.0824(3) 0.6699(2) 0.0693(8) Uani 1 1 d . . . . .
H4 H 0.6365 0.0416 0.6592 0.083 Uiso 1 1 calc R U . . .
C5 C 0.7077(4) 0.2113(3) 0.62122(19) 0.0581(7) Uani 1 1 d . . . . .
H5 H 0.6070 0.2564 0.5785 0.070 Uiso 1 1 calc R U . . .
C6 C 0.8416(3) 0.2714(2) 0.63725(15) 0.0437(5) Uani 1 1 d . . . . .
C7 C 0.9931(4) 0.2069(2) 0.70033(17) 0.0488(6) Uani 1 1 d . . . . .
H7 H 1.0821 0.2477 0.7109 0.059 Uiso 1 1 calc R U . . .
N8 N 0.8220(3) 0.40750(18) 0.58533(13) 0.0448(5) Uani 1 1 d . . . . .
H8A H 0.8487 0.4222 0.5228 0.067 Uiso 1 1 calc R U . . .
H8B H 0.9105 0.4345 0.6057 0.067 Uiso 1 1 calc R U . . .
H8C H 0.6951 0.4478 0.5962 0.067 Uiso 1 1 calc R U . . .
P11 P 0.25826(9) 0.53363(6) 0.66358(4) 0.0437(2) Uani 1 1 d . . . . .
O12 O 0.4536(3) 0.55099(17) 0.60495(12) 0.0553(4) Uani 1 1 d . . . . .
O13 O 0.0821(3) 0.53472(17) 0.61567(12) 0.0525(4) Uani 1 1 d . . . . .
O14 O 0.2018(2) 0.64126(16) 0.71120(12) 0.0515(4) Uani 1 1 d . . . . .
C15 C 0.0253(4) 0.6591(2) 0.77219(17) 0.0468(5) Uani 1 1 d . . . . .
C16 C 0.0500(5) 0.6398(3) 0.8663(2) 0.0658(7) Uani 1 1 d . . . . .
H16 H 0.1796 0.6113 0.8893 0.079 Uiso 1 1 calc R U . . .
C17 C -0.1224(6) 0.6639(3) 0.9257(2) 0.0816(10) Uani 1 1 d . . . . .
H17 H -0.1081 0.6513 0.9891 0.098 Uiso 1 1 calc R U . . .
C18 C -0.3133(5) 0.7060(3) 0.8923(3) 0.0805(10) Uani 1 1 d . . . . .
H18 H -0.4279 0.7211 0.9330 0.097 Uiso 1 1 calc R U . . .
C19 C -0.3358(5) 0.7262(3) 0.7979(3) 0.0731(8) Uani 1 1 d . . . . .
H19 H -0.4653 0.7558 0.7748 0.088 Uiso 1 1 calc R U . . .
C20 C -0.1650(4) 0.7022(3) 0.7375(2) 0.0572(6) Uani 1 1 d . . . . .
H20 H -0.1795 0.7152 0.6741 0.069 Uiso 1 1 calc R U . . .
O21 O 0.2857(3) 0.40268(16) 0.75376(12) 0.0541(4) Uani 1 1 d . . . . .
C22 C 0.4530(4) 0.3512(2) 0.81101(16) 0.0482(6) Uani 1 1 d . . . . .
C23 C 0.4843(4) 0.2229(3) 0.86249(18) 0.0597(7) Uani 1 1 d . . . . .
H23 H 0.3971 0.1763 0.8584 0.072 Uiso 1 1 calc R U . . .
C24 C 0.6472(5) 0.1656(3) 0.9199(2) 0.0722(8) Uani 1 1 d . . . . .
H24 H 0.6699 0.0799 0.9544 0.087 Uiso 1 1 calc R U . . .
C25 C 0.7769(5) 0.2354(3) 0.9265(2) 0.0717(8) Uani 1 1 d . . . . .
H25 H 0.8855 0.1964 0.9655 0.086 Uiso 1 1 calc R U . . .
C26 C 0.7444(5) 0.3629(3) 0.8750(2) 0.0693(8) Uani 1 1 d . . . . .
H26 H 0.8323 0.4090 0.8793 0.083 Uiso 1 1 calc R U . . .
C27 C 0.5812(4) 0.4230(3) 0.8168(2) 0.0608(7) Uani 1 1 d . . . . .
H27 H 0.5584 0.5088 0.7826 0.073 Uiso 1 1 calc R U . . .
C31 C 0.4797(9) 0.1275(4) 0.4618(3) 0.0942(13) Uani 1 1 d . . . . .
H31 H 0.4653 0.2141 0.4366 0.113 Uiso 1 1 calc R U . . .
C32 C 0.3191(7) 0.0763(5) 0.5146(3) 0.1011(13) Uani 1 1 d . . . . .
H32 H 0.1947 0.1283 0.5241 0.121 Uiso 1 1 calc R U . . .
C33 C 0.3413(7) -0.0518(5) 0.5534(3) 0.0969(12) Uani 1 1 d . . . . .
H33 H 0.2329 -0.0863 0.5902 0.116 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 1.749(3) . ?
C2 C3 1.388(4) . ?
C2 C7 1.403(4) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.399(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.383(3) . ?
C6 N8 1.477(3) . ?
C7 H7 0.9300 . ?
N8 H8A 0.8900 . ?
N8 H8B 0.8900 . ?
N8 H8C 0.8900 . ?
P11 O12 1.4823(18) . ?
P11 O13 1.4924(17) . ?
P11 O14 1.6187(18) . ?
P11 O21 1.6192(19) . ?
O14 C15 1.405(3) . ?
C15 C20 1.372(3) . ?
C15 C16 1.386(4) . ?
C16 C17 1.387(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.368(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
O21 C22 1.405(3) . ?
C22 C23 1.392(4) . ?
C22 C27 1.396(4) . ?
C23 C24 1.385(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.395(4) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C31 C33 1.349(6) 2_656 ?
C31 C32 1.371(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.375(6) . ?
C32 H32 0.9300 . ?
C33 C31 1.349(6) 2_656 ?
C33 H33 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 C2 C7 122.4(3) . . ?
C3 C2 Cl1 118.7(2) . . ?
C7 C2 Cl1 118.9(2) . . ?
C2 C3 C4 118.5(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 121.6(2) . . ?
C7 C6 N8 119.3(2) . . ?
C5 C6 N8 119.1(2) . . ?
C6 C7 C2 117.5(2) . . ?
C6 C7 H7 121.2 . . ?
C2 C7 H7 121.2 . . ?
C6 N8 H8A 109.5 . . ?
C6 N8 H8B 109.5 . . ?
H8A N8 H8B 109.5 . . ?
C6 N8 H8C 109.5 . . ?
H8A N8 H8C 109.5 . . ?
H8B N8 H8C 109.5 . . ?
O12 P11 O13 118.15(10) . . ?
O12 P11 O14 104.95(10) . . ?
O13 P11 O14 111.52(10) . . ?
O12 P11 O21 112.19(10) . . ?
O13 P11 O21 104.64(10) . . ?
O14 P11 O21 104.72(10) . . ?
C15 O14 P11 123.85(14) . . ?
C20 C15 C16 121.1(2) . . ?
C20 C15 O14 120.6(2) . . ?
C16 C15 O14 118.2(2) . . ?
C15 C16 C17 118.6(3) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 120.9(3) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 119.9(3) . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 C20 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 C19 119.5(3) . . ?
C15 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C22 O21 P11 125.09(15) . . ?
C23 C22 C27 121.4(2) . . ?
C23 C22 O21 115.9(2) . . ?
C27 C22 O21 122.7(2) . . ?
C24 C23 C22 119.1(3) . . ?
C24 C23 H23 120.5 . . ?
C22 C23 H23 120.5 . . ?
C23 C24 C25 120.5(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C25 C26 C27 120.7(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 118.4(3) . . ?
C26 C27 H27 120.8 . . ?
C22 C27 H27 120.8 . . ?
C33 C31 C32 119.8(4) 2_656 . ?
C33 C31 H31 120.1 2_656 . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.2(4) . . ?
C31 C32 H32 119.9 . . ?
C33 C32 H32 119.9 . . ?
C31 C33 C32 120.0(4) 2_656 . ?
C31 C33 H33 120.0 2_656 . ?
C32 C33 H33 120.0 . . ?

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 C2 C3 C4 1.0(4) . . . . ?
Cl1 C2 C3 C4 -178.8(2) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 0.3(4) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C4 C5 C6 N8 179.8(2) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
N8 C6 C7 C2 -179.6(2) . . . . ?
C3 C2 C7 C6 -0.7(4) . . . . ?
Cl1 C2 C7 C6 179.12(18) . . . . ?
O12 P11 O14 C15 179.45(17) . . . . ?
O13 P11 O14 C15 50.4(2) . . . . ?
O21 P11 O14 C15 -62.23(19) . . . . ?
P11 O14 C15 C20 -68.5(3) . . . . ?
P11 O14 C15 C16 115.6(2) . . . . ?
C20 C15 C16 C17 0.6(4) . . . . ?
O14 C15 C16 C17 176.4(3) . . . . ?
C15 C16 C17 C18 -0.1(5) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.8(5) . . . . ?
C16 C15 C20 C19 -0.4(4) . . . . ?
O14 C15 C20 C19 -176.1(2) . . . . ?
C18 C19 C20 C15 -0.3(4) . . . . ?
O12 P11 O21 C22 40.0(2) . . . . ?
O13 P11 O21 C22 169.26(18) . . . . ?
O14 P11 O21 C22 -73.31(19) . . . . ?
P11 O21 C22 C23 -159.21(18) . . . . ?
P11 O21 C22 C27 20.9(3) . . . . ?
C27 C22 C23 C24 -0.5(4) . . . . ?
O21 C22 C23 C24 179.6(2) . . . . ?
C22 C23 C24 C25 0.3(4) . . . . ?
C23 C24 C25 C26 -0.3(5) . . . . ?
C24 C25 C26 C27 0.5(5) . . . . ?
C25 C26 C27 C22 -0.6(4) . . . . ?
C23 C22 C27 C26 0.6(4) . . . . ?
O21 C22 C27 C26 -179.5(2) . . . . ?
C33 C31 C32 C33 1.2(6) 2_656 . . . ?
C31 C32 C33 C31 -1.2(6) . . . 2_656 ?

_refine_diff_density_max         0.304
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1423374'
_audit_update_record             
;
2015-09-09 deposited with the CCDC.
2015-11-13 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         'C13 H15 Cl N2 S'
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.4353(4)
_cell_length_b                   14.9782(9)
_cell_length_c                   11.5168(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.453(6)
_cell_angle_gamma                90
_cell_volume                     1409.05(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    2563
_cell_measurement_theta_min      3.0230
_cell_measurement_theta_max      24.9910

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.400
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.61293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?




_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '122 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9066
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0441
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         25.236
_diffrn_reflns_theta_full        25.236
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2524
_reflns_number_gt                1830
_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       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;
_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)+(0.1146P)²+0.4718P] 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         2524
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0552
_refine_ls_wR_factor_ref         0.1878
_refine_ls_wR_factor_gt          0.1681
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_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
Cl1 Cl 1.23323(11) 0.97147(7) 0.53939(9) 0.0786(4) Uani 1 1 d . . . . .
C2 C 1.1942(4) 0.9550(2) 0.3858(3) 0.0596(8) Uani 1 1 d . . . . .
C3 C 1.3075(4) 0.9822(2) 0.3264(4) 0.0708(10) Uani 1 1 d . . . . .
H3 H 1.4037 1.0101 0.3674 0.085 Uiso 1 1 calc R U . . .
C4 C 1.2763(5) 0.9674(3) 0.2048(4) 0.0789(11) Uani 1 1 d . . . . .
H4 H 1.3531 0.9847 0.1637 0.095 Uiso 1 1 calc R U . . .
C5 C 1.1323(4) 0.9274(3) 0.1430(3) 0.0730(10) Uani 1 1 d . . . . .
H5 H 1.1119 0.9179 0.0608 0.088 Uiso 1 1 calc R U . . .
C6 C 1.0203(3) 0.9020(2) 0.2043(3) 0.0572(8) Uani 1 1 d . . . . .
C7 C 1.0503(4) 0.9144(2) 0.3263(3) 0.0577(8) Uani 1 1 d . . . . .
H7 H 0.9747 0.8957 0.3678 0.069 Uiso 1 1 calc R U . . .
N8 N 0.8708(3) 0.85940(17) 0.1405(2) 0.0604(7) Uani 1 1 d . . . . .
C9 C 0.7348(3) 0.9103(2) 0.0975(3) 0.0522(7) Uani 1 1 d . . . . .
N10 N 0.6071(3) 0.87188(17) 0.0256(2) 0.0635(7) Uani 1 1 d . . . . .
H10 H 0.5185 0.9028 0.0070 0.076 Uiso 1 1 calc R U . . .
C11 C 0.5992(5) 0.7819(2) -0.0263(3) 0.0765(11) Uani 1 1 d . . . . .
C12 C 0.7380(5) 0.7293(3) 0.0455(4) 0.0899(13) Uani 1 1 d . . . . .
H12 H 0.7337 0.6675 0.0381 0.108 Uiso 1 1 calc R U . . .
C13 C 0.8683(4) 0.7654(2) 0.1197(4) 0.0747(10) Uani 1 1 d . . . . .
S14 S 0.72835(10) 1.01859(5) 0.13711(8) 0.0632(3) Uani 1 1 d . . . . .
C15 C 0.4371(6) 0.7409(3) -0.0198(7) 0.153(3) Uani 1 1 d . . . . .
H15A H 0.4304 0.7394 0.0621 0.229 Uiso 1 1 calc R U . . .
H15B H 0.4298 0.6813 -0.0512 0.229 Uiso 1 1 calc R U . . .
H15C H 0.3488 0.7761 -0.0663 0.229 Uiso 1 1 calc R U . . .
C16 C 0.6077(11) 0.7903(4) -0.1556(5) 0.177(4) Uani 1 1 d . . . . .
H16A H 0.5210 0.8285 -0.1981 0.266 Uiso 1 1 calc R U . . .
H16B H 0.5962 0.7324 -0.1923 0.266 Uiso 1 1 calc R U . . .
H16C H 0.7113 0.8155 -0.1585 0.266 Uiso 1 1 calc R U . . .
C17 C 1.0095(6) 0.7121(3) 0.1888(7) 0.137(2) Uani 1 1 d . . . . .
H17A H 0.9865 0.6496 0.1753 0.206 Uiso 1 1 calc R U . . .
H17B H 1.0273 0.7250 0.2727 0.206 Uiso 1 1 calc R U . . .
H17C H 1.1058 0.7273 0.1629 0.206 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 1.735(4) . ?
C2 C3 1.368(5) . ?
C2 C7 1.378(4) . ?
C3 C4 1.376(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(4) . ?
C6 N8 1.440(4) . ?
C7 H7 0.9300 . ?
N8 C9 1.364(4) . ?
N8 C13 1.428(4) . ?
C9 N10 1.316(4) . ?
C9 S14 1.689(3) . ?
N10 C11 1.469(4) . ?
N10 H10 0.8600 . ?
C11 C12 1.481(5) . ?
C11 C16 1.514(7) . ?
C11 C15 1.517(6) . ?
C12 C13 1.327(5) . ?
C12 H12 0.9300 . ?
C13 C17 1.488(6) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C3 C2 C7 121.4(3) . . ?
C3 C2 Cl1 119.3(3) . . ?
C7 C2 Cl1 119.3(3) . . ?
C2 C3 C4 118.7(3) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C5 120.9(3) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C6 C5 C4 119.1(3) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.0(3) . . ?
C5 C6 N8 119.3(3) . . ?
C7 C6 N8 119.7(3) . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 H7 120.6 . . ?
C2 C7 H7 120.6 . . ?
C9 N8 C13 121.0(3) . . ?
C9 N8 C6 119.2(2) . . ?
C13 N8 C6 119.8(2) . . ?
N10 C9 N8 117.8(3) . . ?
N10 C9 S14 120.9(2) . . ?
N8 C9 S14 121.3(2) . . ?
C9 N10 C11 127.2(3) . . ?
C9 N10 H10 116.4 . . ?
C11 N10 H10 116.4 . . ?
N10 C11 C12 108.2(3) . . ?
N10 C11 C16 108.4(3) . . ?
C12 C11 C16 111.6(4) . . ?
N10 C11 C15 107.6(4) . . ?
C12 C11 C15 110.7(4) . . ?
C16 C11 C15 110.3(5) . . ?
C13 C12 C11 123.7(3) . . ?
C13 C12 H12 118.1 . . ?
C11 C12 H12 118.1 . . ?
C12 C13 N8 119.0(3) . . ?
C12 C13 C17 123.4(3) . . ?
N8 C13 C17 117.6(3) . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C16 H16A 109.5 . . ?
C11 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C11 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C2 C3 C4 -0.7(5) . . . . ?
Cl1 C2 C3 C4 179.0(3) . . . . ?
C2 C3 C4 C5 1.1(6) . . . . ?
C3 C4 C5 C6 -0.2(6) . . . . ?
C4 C5 C6 C7 -1.1(5) . . . . ?
C4 C5 C6 N8 -179.4(3) . . . . ?
C5 C6 C7 C2 1.5(5) . . . . ?
N8 C6 C7 C2 179.8(3) . . . . ?
C3 C2 C7 C6 -0.6(5) . . . . ?
Cl1 C2 C7 C6 179.7(2) . . . . ?
C5 C6 N8 C9 -93.5(4) . . . . ?
C7 C6 N8 C9 88.2(4) . . . . ?
C5 C6 N8 C13 84.5(4) . . . . ?
C7 C6 N8 C13 -93.8(4) . . . . ?
C13 N8 C9 N10 -7.2(5) . . . . ?
C6 N8 C9 N10 170.7(3) . . . . ?
C13 N8 C9 S14 171.6(3) . . . . ?
C6 N8 C9 S14 -10.4(4) . . . . ?
N8 C9 N10 C11 -7.9(5) . . . . ?
S14 C9 N10 C11 173.3(3) . . . . ?
C9 N10 C11 C12 19.0(5) . . . . ?
C9 N10 C11 C16 -102.2(5) . . . . ?
C9 N10 C11 C15 138.6(4) . . . . ?
N10 C11 C12 C13 -17.2(6) . . . . ?
C16 C11 C12 C13 102.0(5) . . . . ?
C15 C11 C12 C13 -134.8(5) . . . . ?
C11 C12 C13 N8 5.6(6) . . . . ?
C11 C12 C13 C17 -178.2(5) . . . . ?
C9 N8 C13 C12 8.2(5) . . . . ?
C6 N8 C13 C12 -169.7(4) . . . . ?
C9 N8 C13 C17 -168.3(4) . . . . ?
C6 N8 C13 C17 13.8(6) . . . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.046

