# 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_5d
_database_code_depnum_ccdc_archive 'CCDC 1411063'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
(2E)-N-(2-methoxyphenyl)-2-(2,3,4,4a-tetrahydro-1H-xanthen-1-ylidene)hydrazinecarbothioamide
_chemical_formula_moiety         'C21 H21 N3 O2 S'
_chemical_formula_sum            'C21 H21 N3 O2 S'
_chemical_formula_iupac          'C21 H21 N3 O2 S'
_chemical_formula_weight         379.47

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   8.1682(11)
_cell_length_b                   10.1121(12)
_cell_length_c                   12.2265(15)
_cell_angle_alpha                106.817(5)
_cell_angle_beta                 96.610(5)
_cell_angle_gamma                94.955(5)
_cell_volume                     952.6(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2180
_cell_measurement_theta_min      2.121
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.30
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    0.191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.930
_exptl_absorpt_correction_T_max  0.943
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.70
_diffrn_reflns_number            13685
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3973
_reflns_number_gt                2180
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1230
_refine_ls_R_factor_gt           0.0641
_refine_ls_wR_factor_ref         0.2036
_refine_ls_wR_factor_gt          0.1710
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         3973
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0994P)²+0.1731P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50083(11) 0.83801(10) -0.14751(7) 0.0702(4) Uani 1 1 d . . . . .
O1 O 1.2480(3) 0.9827(2) 0.4463(2) 0.0782(8) Uani 1 1 d . . . . .
O2 O 0.7845(3) 0.4596(2) -0.0057(2) 0.0737(7) Uani 1 1 d . . . . .
N1 N 0.8346(3) 0.8584(2) 0.11196(19) 0.0482(6) Uani 1 1 d . . . . .
N2 N 0.7281(3) 0.8930(3) 0.0328(2) 0.0550(7) Uani 1 1 d . . . . .
H2A H 0.7214 0.9791 0.0385 0.066 Uiso 1 1 calc R U . . .
N3 N 0.6635(3) 0.6628(2) -0.0573(2) 0.0543(7) Uani 1 1 d . . . . .
H3A H 0.7421 0.6619 -0.0044 0.065 Uiso 1 1 calc R U . . .
C1 C 1.2418(4) 0.8482(3) 0.4481(2) 0.0489(7) Uani 1 1 d . . . . .
C2 C 1.3504(4) 0.8185(4) 0.5298(3) 0.0650(9) Uani 1 1 d . . . . .
H2 H 1.4276 0.8887 0.5807 0.078 Uiso 1 1 calc R U . . .
C3 C 1.3445(5) 0.6847(4) 0.5360(3) 0.0761(11) Uani 1 1 d . . . . .
H3 H 1.4196 0.6637 0.5899 0.091 Uiso 1 1 calc R U . . .
C4 C 1.2281(6) 0.5824(4) 0.4629(3) 0.0919(13) Uani 1 1 d . . . . .
H4 H 1.2223 0.4921 0.4678 0.110 Uiso 1 1 calc R U . . .
C5 C 1.1201(5) 0.6137(4) 0.3821(3) 0.0849(12) Uani 1 1 d . . . . .
H5 H 1.0414 0.5434 0.3329 0.102 Uiso 1 1 calc R U . . .
C6 C 1.1242(4) 0.7453(3) 0.3717(2) 0.0507(7) Uani 1 1 d . . . . .
C7 C 1.0163(4) 0.7841(3) 0.2874(2) 0.0531(8) Uani 1 1 d . . . . .
H7 H 0.9346 0.7172 0.2375 0.064 Uiso 1 1 calc R U . . .
C8 C 1.0301(3) 0.9125(3) 0.2790(2) 0.0438(7) Uani 1 1 d . . . . .
C9 C 1.1646(5) 1.0163(3) 0.3589(4) 0.0894(13) Uani 1 1 d . . . . .
H9 H 1.2500 1.0034 0.3079 0.107 Uiso 1 1 calc R U . . .
C10 C 1.1558(5) 1.1604(3) 0.3731(3) 0.0777(11) Uani 1 1 d . . . . .
H10A H 1.2688 1.2067 0.3886 0.093 Uiso 1 1 calc R U . . .
H10B H 1.1054 1.1972 0.4419 0.093 Uiso 1 1 calc R U . . .
C11 C 1.0681(5) 1.2019(4) 0.2816(4) 0.0980(14) Uani 1 1 d . . . . .
H11A H 1.1486 1.2208 0.2339 0.118 Uiso 1 1 calc R U . . .
H11B H 1.0274 1.2893 0.3168 0.118 Uiso 1 1 calc R U . . .
C12 C 0.9295(4) 1.1085(3) 0.2055(3) 0.0746(11) Uani 1 1 d . . . . .
H12A H 0.9285 1.1198 0.1293 0.090 Uiso 1 1 calc R U . . .
H12B H 0.8279 1.1385 0.2327 0.090 Uiso 1 1 calc R U . . .
C13 C 0.9251(3) 0.9563(3) 0.1930(2) 0.0455(7) Uani 1 1 d . . . . .
C14 C 0.6328(4) 0.7910(3) -0.0549(2) 0.0479(7) Uani 1 1 d . . . . .
C15 C 0.5943(4) 0.5286(3) -0.1281(2) 0.0533(8) Uani 1 1 d . . . . .
C16 C 0.4679(4) 0.4993(4) -0.2213(3) 0.0731(10) Uani 1 1 d . . . . .
H16 H 0.4222 0.5708 -0.2427 0.088 Uiso 1 1 calc R U . . .
C17 C 0.4113(6) 0.3605(5) -0.2820(3) 0.0965(14) Uani 1 1 d . . . . .
H17 H 0.3288 0.3398 -0.3457 0.116 Uiso 1 1 calc R U . . .
C18 C 0.4735(6) 0.2554(5) -0.2503(4) 0.0980(15) Uani 1 1 d . . . . .
H18 H 0.4324 0.1636 -0.2917 0.118 Uiso 1 1 calc R U . . .
C19 C 0.5972(5) 0.2827(4) -0.1574(4) 0.0809(12) Uani 1 1 d . . . . .
H19 H 0.6385 0.2101 -0.1350 0.097 Uiso 1 1 calc R U . . .
C20 C 0.6596(4) 0.4199(3) -0.0974(3) 0.0601(9) Uani 1 1 d . . . . .
C21 C 0.8576(5) 0.3563(4) 0.0324(4) 0.0906(12) Uani 1 1 d . . . . .
H21A H 0.9046 0.2972 -0.0295 0.136 Uiso 1 1 calc R U . . .
H21B H 0.7745 0.3016 0.0559 0.136 Uiso 1 1 calc R U . . .
H21C H 0.9435 0.3998 0.0965 0.136 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C14 1.670(3) . ?
O1 C9 1.343(4) . ?
O1 C1 1.363(3) . ?
O2 C20 1.366(4) . ?
O2 C21 1.410(4) . ?
N1 C13 1.283(3) . ?
N1 N2 1.368(3) . ?
N2 C14 1.360(4) . ?
N2 H2A 0.8600 . ?
N3 C14 1.335(4) . ?
N3 C15 1.409(4) . ?
N3 H3A 0.8600 . ?
C1 C2 1.376(4) . ?
C1 C6 1.391(4) . ?
C2 C3 1.374(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.441(4) . ?
C7 C8 1.329(4) . ?
C7 H7 0.9300 . ?
C8 C13 1.470(4) . ?
C8 C9 1.491(4) . ?
C9 C10 1.426(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.441(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.450(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.499(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C15 C20 1.388(5) . ?
C15 C16 1.391(4) . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.351(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.387(5) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C9 O1 C1 121.5(2) . . ?
C20 O2 C21 119.1(3) . . ?
C13 N1 N2 118.8(2) . . ?
C14 N2 N1 119.8(2) . . ?
C14 N2 H2A 120.1 . . ?
N1 N2 H2A 120.1 . . ?
C14 N3 C15 133.6(3) . . ?
C14 N3 H3A 113.2 . . ?
C15 N3 H3A 113.2 . . ?
O1 C1 C2 118.2(3) . . ?
O1 C1 C6 120.5(2) . . ?
C2 C1 C6 121.2(3) . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 122.2(3) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C7 124.8(3) . . ?
C1 C6 C7 118.0(3) . . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 123.9(2) . . ?
C7 C8 C9 117.5(3) . . ?
C13 C8 C9 118.5(2) . . ?
O1 C9 C10 117.5(3) . . ?
O1 C9 C8 118.8(3) . . ?
C10 C9 C8 118.3(3) . . ?
O1 C9 H9 97.7 . . ?
C10 C9 H9 97.7 . . ?
C8 C9 H9 97.7 . . ?
C9 C10 C11 119.6(3) . . ?
C9 C10 H10A 107.4 . . ?
C11 C10 H10A 107.4 . . ?
C9 C10 H10B 107.4 . . ?
C11 C10 H10B 107.4 . . ?
H10A C10 H10B 106.9 . . ?
C10 C11 C12 119.3(3) . . ?
C10 C11 H11A 107.5 . . ?
C12 C11 H11A 107.5 . . ?
C10 C11 H11B 107.5 . . ?
C12 C11 H11B 107.5 . . ?
H11A C11 H11B 107.0 . . ?
C11 C12 C13 117.4(3) . . ?
C11 C12 H12A 107.9 . . ?
C13 C12 H12A 107.9 . . ?
C11 C12 H12B 107.9 . . ?
C13 C12 H12B 107.9 . . ?
H12A C12 H12B 107.2 . . ?
N1 C13 C8 116.1(2) . . ?
N1 C13 C12 124.8(3) . . ?
C8 C13 C12 119.1(2) . . ?
N3 C14 N2 113.6(2) . . ?
N3 C14 S1 128.1(2) . . ?
N2 C14 S1 118.2(2) . . ?
C20 C15 C16 119.6(3) . . ?
C20 C15 N3 114.9(3) . . ?
C16 C15 N3 125.5(3) . . ?
C15 C16 C17 118.6(4) . . ?
C15 C16 H16 120.7 . . ?
C17 C16 H16 120.7 . . ?
C18 C17 C16 121.4(4) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 120.6(4) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C18 C19 C20 119.2(4) . . ?
C18 C19 H19 120.4 . . ?
C20 C19 H19 120.4 . . ?
O2 C20 C19 124.4(4) . . ?
O2 C20 C15 115.1(3) . . ?
C19 C20 C15 120.5(4) . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C13 N1 N2 C14 179.0(2) . . . . ?
C9 O1 C1 C2 169.6(3) . . . . ?
C9 O1 C1 C6 -12.7(5) . . . . ?
O1 C1 C2 C3 178.3(3) . . . . ?
C6 C1 C2 C3 0.6(5) . . . . ?
C1 C2 C3 C4 -1.6(5) . . . . ?
C2 C3 C4 C5 1.3(6) . . . . ?
C3 C4 C5 C6 0.0(7) . . . . ?
C4 C5 C6 C1 -1.0(6) . . . . ?
C4 C5 C6 C7 178.8(4) . . . . ?
O1 C1 C6 C5 -176.9(3) . . . . ?
C2 C1 C6 C5 0.7(5) . . . . ?
O1 C1 C6 C7 3.2(4) . . . . ?
C2 C1 C6 C7 -179.2(3) . . . . ?
C5 C6 C7 C8 -177.7(3) . . . . ?
C1 C6 C7 C8 2.2(4) . . . . ?
C6 C7 C8 C13 178.8(3) . . . . ?
C6 C7 C8 C9 1.2(5) . . . . ?
C1 O1 C9 C10 169.8(3) . . . . ?
C1 O1 C9 C8 16.0(6) . . . . ?
C7 C8 C9 O1 -10.1(5) . . . . ?
C13 C8 C9 O1 172.1(3) . . . . ?
C7 C8 C9 C10 -163.8(4) . . . . ?
C13 C8 C9 C10 18.5(5) . . . . ?
O1 C9 C10 C11 179.8(4) . . . . ?
C8 C9 C10 C11 -26.2(6) . . . . ?
C9 C10 C11 C12 29.5(6) . . . . ?
C10 C11 C12 C13 -24.0(6) . . . . ?
N2 N1 C13 C8 176.7(2) . . . . ?
N2 N1 C13 C12 -3.0(5) . . . . ?
C7 C8 C13 N1 -11.2(4) . . . . ?
C9 C8 C13 N1 166.4(3) . . . . ?
C7 C8 C13 C12 168.5(3) . . . . ?
C9 C8 C13 C12 -13.9(4) . . . . ?
C11 C12 C13 N1 -163.7(3) . . . . ?
C11 C12 C13 C8 16.6(5) . . . . ?
C15 N3 C14 N2 177.9(3) . . . . ?
C15 N3 C14 S1 -4.7(5) . . . . ?
N1 N2 C14 N3 -3.9(4) . . . . ?
N1 N2 C14 S1 178.4(2) . . . . ?
C14 N3 C15 C20 -177.5(3) . . . . ?
C14 N3 C15 C16 1.2(5) . . . . ?
C20 C15 C16 C17 -0.4(5) . . . . ?
N3 C15 C16 C17 -179.1(3) . . . . ?
C15 C16 C17 C18 1.7(6) . . . . ?
C16 C17 C18 C19 -0.9(6) . . . . ?
C17 C18 C19 C20 -1.1(6) . . . . ?
C21 O2 C20 C19 0.2(5) . . . . ?
C21 O2 C20 C15 179.5(3) . . . . ?
C18 C19 C20 O2 -178.5(3) . . . . ?
C18 C19 C20 C15 2.3(5) . . . . ?
C16 C15 C20 O2 179.2(3) . . . . ?
N3 C15 C20 O2 -2.0(4) . . . . ?
C16 C15 C20 C19 -1.5(5) . . . . ?
N3 C15 C20 C19 177.3(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A S1 0.86 2.86 3.484(3) 130.4 2_675
N3 H3A O2 0.86 2.10 2.560(3) 112.9 .
N3 H3A N1 0.86 2.10 2.576(3) 114.5 .
C12 H12B S1 0.97 2.82 3.623(4) 140.6 2_675
C16 H16 S1 0.93 2.60 3.258(4) 127.9 .

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.052

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_5i
_database_code_depnum_ccdc_archive 'CCDC 1411064'
_audit_update_record             
;
2015-07-07 deposited with the CCDC.
2015-09-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
(2E)-N-(2,4-dichlorophenyl)-2-(2,3,4,4a-tetrahydro-1H-xanthen-1-ylidene)hydrazinecarbothioamide
_chemical_formula_moiety         'C20 H17 Cl2 N3 O S'
_chemical_formula_sum            'C20 H17 Cl2 N3 O S'
_chemical_formula_iupac          'C20 H17 Cl2 N3 O S'
_chemical_formula_weight         418.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6988(10)
_cell_length_b                   9.8693(9)
_cell_length_c                   10.7502(12)
_cell_angle_alpha                101.697(6)
_cell_angle_beta                 101.627(6)
_cell_angle_gamma                101.570(6)
_cell_volume                     955.19(17)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2684
_cell_measurement_theta_min      2.556
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.25
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    0.465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.835
_exptl_absorpt_correction_T_max  0.895
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.90
_diffrn_reflns_number            13033
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.556
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_max 0.968
_diffrn_measured_fraction_theta_full 0.968
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3619
_reflns_number_gt                2684
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0606
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1567
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         3619
_refine_ls_number_parameters     239
_refine_ls_number_restraints     4
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0667P)²+0.8654P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;


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 0.21976(12) 1.35792(12) 0.40831(11) 0.0806(4) Uani 1 1 d . . . . .
Cl2 Cl 0.29252(11) 0.83958(12) 0.21094(12) 0.0861(4) Uani 1 1 d . . . . .
S1 S 0.87468(11) 1.13141(10) 0.43371(14) 0.0837(4) Uani 1 1 d . . . . .
O1 O 0.5626(3) 0.2347(3) 0.0689(3) 0.0867(9) Uani 1 1 d . . . . .
N1 N 0.6845(3) 0.7305(3) 0.2852(3) 0.0482(6) Uani 1 1 d . . . . .
N2 N 0.7864(3) 0.8561(3) 0.3455(3) 0.0546(7) Uani 1 1 d . . . . .
H2A H 0.8770 0.8569 0.3652 0.066 Uiso 1 1 calc R U . . .
N3 N 0.6005(3) 0.9625(3) 0.3454(3) 0.0515(7) Uani 1 1 d . . . . .
H3A H 0.5515 0.8756 0.3088 0.062 Uiso 1 1 calc R U . . .
C1 C 0.4168(4) 0.2242(4) 0.0464(4) 0.0590(9) Uani 1 1 d . . . . .
C2 C 0.3209(5) 0.0952(4) -0.0231(4) 0.0731(11) Uani 1 1 d . . . . .
H2 H 0.3557 0.0166 -0.0525 0.088 Uiso 1 1 calc R U . . .
C3 C 0.1753(5) 0.0834(5) -0.0485(4) 0.0811(12) Uani 1 1 d . . . . .
H3 H 0.1111 -0.0034 -0.0965 0.097 Uiso 1 1 calc R U . . .
C4 C 0.1215(5) 0.1982(5) -0.0042(4) 0.0780(12) Uani 1 1 d . . . . .
H4 H 0.0216 0.1885 -0.0204 0.094 Uiso 1 1 calc R U . . .
C5 C 0.2175(4) 0.3279(4) 0.0646(4) 0.0667(10) Uani 1 1 d . . . . .
H5 H 0.1817 0.4062 0.0929 0.080 Uiso 1 1 calc R U . . .
C6 C 0.3669(4) 0.3427(4) 0.0919(3) 0.0548(8) Uani 1 1 d . . . . .
C7 C 0.4740(4) 0.4755(4) 0.1621(4) 0.0588(9) Uani 1 1 d . . . . .
H7 H 0.4425 0.5570 0.1894 0.071 Uiso 1 1 calc R U . . .
C8 C 0.6164(4) 0.4844(3) 0.1886(3) 0.0519(8) Uani 1 1 d D . . . .
C9A C 0.6567(7) 0.3439(7) 0.1732(9) 0.0646(9) Uani 0.596(6) 1 d . . P A 1
H9A H 0.6562 0.3135 0.2545 0.078 Uiso 0.596(6) 1 calc R U P A 1
C10A C 0.8067(11) 0.3553(11) 0.1503(9) 0.0646(9) Uani 0.596(6) 1 d . . P A 1
H10A H 0.8121 0.3871 0.0713 0.078 Uiso 0.596(6) 1 calc R U P A 1
H10B H 0.8307 0.2636 0.1412 0.078 Uiso 0.596(6) 1 calc R U P A 1
C11A C 0.9125(7) 0.4672(6) 0.2734(8) 0.0646(9) Uani 0.596(6) 1 d . . P A 1
H11A H 1.0123 0.4681 0.2719 0.078 Uiso 0.596(6) 1 calc R U P A 1
H11B H 0.8955 0.4416 0.3525 0.078 Uiso 0.596(6) 1 calc R U P A 1
C12A C 0.887(2) 0.6195(14) 0.2737(17) 0.0646(9) Uani 0.596(6) 1 d . . P A 1
H12A H 0.9411 0.6860 0.3568 0.078 Uiso 0.596(6) 1 calc R U P A 1
H12B H 0.9228 0.6528 0.2045 0.078 Uiso 0.596(6) 1 calc R U P A 1
C9B C 0.6592(10) 0.3572(10) 0.1078(12) 0.0646(9) Uani 0.404(6) 1 d D . P A 2
H9B H 0.6719 0.3840 0.0271 0.078 Uiso 0.404(6) 1 calc R U P A 2
C10B C 0.8140(14) 0.3519(16) 0.1815(14) 0.0646(9) Uani 0.404(6) 1 d D . P A 2
H10C H 0.8129 0.3396 0.2686 0.078 Uiso 0.404(6) 1 calc R U P A 2
H10D H 0.8420 0.2717 0.1339 0.078 Uiso 0.404(6) 1 calc R U P A 2
C11B C 0.9216(10) 0.4900(9) 0.1917(12) 0.0646(9) Uani 0.404(6) 1 d D . P A 2
H11C H 0.9137 0.5093 0.1059 0.078 Uiso 0.404(6) 1 calc R U P A 2
H11D H 1.0200 0.4836 0.2254 0.078 Uiso 0.404(6) 1 calc R U P A 2
C12B C 0.886(3) 0.608(2) 0.284(2) 0.0646(9) Uani 0.404(6) 1 d D . P A 2
H12C H 0.9473 0.6992 0.2840 0.078 Uiso 0.404(6) 1 calc R U P A 2
H12D H 0.9120 0.5960 0.3726 0.078 Uiso 0.404(6) 1 calc R U P A 2
C13 C 0.7287(4) 0.6169(3) 0.2533(3) 0.0499(8) Uani 1 1 d . . . . .
C14 C 0.7449(4) 0.9800(3) 0.3746(3) 0.0511(8) Uani 1 1 d . . . . .
C15 C 0.5148(3) 1.0599(3) 0.3637(3) 0.0472(7) Uani 1 1 d . . . . .
C16 C 0.5674(4) 1.1988(3) 0.4422(4) 0.0602(9) Uani 1 1 d . . . . .
H16 H 0.6656 1.2317 0.4853 0.072 Uiso 1 1 calc R U . . .
C17 C 0.4759(4) 1.2897(4) 0.4576(4) 0.0637(10) Uani 1 1 d . . . . .
H17 H 0.5124 1.3823 0.5110 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3323(4) 1.2418(4) 0.3937(4) 0.0565(9) Uani 1 1 d . . . . .
C19 C 0.2743(4) 1.1035(4) 0.3187(4) 0.0626(9) Uani 1 1 d . . . . .
H19 H 0.1754 1.0709 0.2782 0.075 Uiso 1 1 calc R U . . .
C20 C 0.3667(4) 1.0138(4) 0.3048(3) 0.0537(8) 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 C18 1.740(3) . ?
Cl2 C20 1.732(3) . ?
S1 C14 1.661(3) . ?
O1 C9B 1.303(11) . ?
O1 C1 1.365(5) . ?
O1 C9A 1.398(8) . ?
N1 C13 1.286(4) . ?
N1 N2 1.363(4) . ?
N2 C14 1.359(4) . ?
N2 H2A 0.8600 . ?
N3 C14 1.339(4) . ?
N3 C15 1.402(4) . ?
N3 H3A 0.8600 . ?
C1 C2 1.379(5) . ?
C1 C6 1.390(5) . ?
C2 C3 1.359(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.380(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.383(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.451(5) . ?
C7 C8 1.333(5) . ?
C7 H7 0.9300 . ?
C8 C13 1.461(5) . ?
C8 C9A 1.502(7) . ?
C8 C9B 1.554(9) . ?
C9A C10A 1.510(13) . ?
C9A H9A 0.9800 . ?
C10A C11A 1.559(12) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C12A 1.571(13) . ?
C11A H11A 0.9700 . ?
C11A H11B 0.9700 . ?
C12A C13 1.499(19) . ?
C12A H12A 0.9700 . ?
C12A H12B 0.9700 . ?
C9B C10B 1.566(15) . ?
C9B H9B 0.9800 . ?
C10B C11B 1.510(15) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B C12B 1.517(17) . ?
C11B H11C 0.9700 . ?
C11B H11D 0.9700 . ?
C12B C13 1.52(3) . ?
C12B H12C 0.9700 . ?
C12B H12D 0.9700 . ?
C15 C20 1.388(5) . ?
C15 C16 1.388(5) . ?
C16 C17 1.393(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.361(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(5) . ?
C19 C20 1.388(5) . ?
C19 H19 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
C9B O1 C1 122.6(4) . . ?
C1 O1 C9A 118.5(4) . . ?
C13 N1 N2 118.1(3) . . ?
C14 N2 N1 120.1(3) . . ?
C14 N2 H2A 119.9 . . ?
N1 N2 H2A 119.9 . . ?
C14 N3 C15 131.7(3) . . ?
C14 N3 H3A 114.2 . . ?
C15 N3 H3A 114.2 . . ?
O1 C1 C2 119.0(3) . . ?
O1 C1 C6 120.0(3) . . ?
C2 C1 C6 121.0(4) . . ?
C3 C2 C1 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 121.0(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.8(4) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.1(3) . . ?
C1 C6 C7 118.0(3) . . ?
C5 C6 C7 123.9(3) . . ?
C8 C7 C6 122.0(3) . . ?
C8 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C7 C8 C13 124.1(3) . . ?
C7 C8 C9A 115.3(4) . . ?
C13 C8 C9A 119.5(4) . . ?
C7 C8 C9B 114.6(5) . . ?
C13 C8 C9B 118.6(5) . . ?
O1 C9A C8 114.1(5) . . ?
O1 C9A C10A 106.0(6) . . ?
C8 C9A C10A 112.0(7) . . ?
O1 C9A H9A 108.1 . . ?
C8 C9A H9A 108.1 . . ?
C10A C9A H9A 108.1 . . ?
C9A C10A C11A 105.6(8) . . ?
C9A C10A H10A 110.6 . . ?
C11A C10A H10A 110.6 . . ?
C9A C10A H10B 110.6 . . ?
C11A C10A H10B 110.6 . . ?
H10A C10A H10B 108.8 . . ?
C10A C11A C12A 109.5(10) . . ?
C10A C11A H11A 109.8 . . ?
C12A C11A H11A 109.8 . . ?
C10A C11A H11B 109.8 . . ?
C12A C11A H11B 109.8 . . ?
H11A C11A H11B 108.2 . . ?
C13 C12A C11A 111.4(11) . . ?
C13 C12A H12A 109.3 . . ?
C11A C12A H12A 109.3 . . ?
C13 C12A H12B 109.3 . . ?
C11A C12A H12B 109.3 . . ?
H12A C12A H12B 108.0 . . ?
O1 C9B C8 116.6(7) . . ?
O1 C9B C10B 114.7(9) . . ?
C8 C9B C10B 108.5(9) . . ?
O1 C9B H9B 105.3 . . ?
C8 C9B H9B 105.3 . . ?
C10B C9B H9B 105.3 . . ?
C11B C10B C9B 108.9(10) . . ?
C11B C10B H10C 109.9 . . ?
C9B C10B H10C 109.9 . . ?
C11B C10B H10D 109.9 . . ?
C9B C10B H10D 109.9 . . ?
H10C C10B H10D 108.3 . . ?
C10B C11B C12B 107.6(13) . . ?
C10B C11B H11C 110.2 . . ?
C12B C11B H11C 110.2 . . ?
C10B C11B H11D 110.2 . . ?
C12B C11B H11D 110.2 . . ?
H11C C11B H11D 108.5 . . ?
C11B C12B C13 115.6(18) . . ?
C11B C12B H12C 108.4 . . ?
C13 C12B H12C 108.4 . . ?
C11B C12B H12D 108.4 . . ?
C13 C12B H12D 108.4 . . ?
H12C C12B H12D 107.4 . . ?
N1 C13 C8 116.6(3) . . ?
N1 C13 C12A 122.5(6) . . ?
C8 C13 C12A 120.9(6) . . ?
N1 C13 C12B 125.4(8) . . ?
C8 C13 C12B 118.0(8) . . ?
N3 C14 N2 113.8(3) . . ?
N3 C14 S1 128.4(2) . . ?
N2 C14 S1 117.8(2) . . ?
C20 C15 C16 117.4(3) . . ?
C20 C15 N3 118.4(3) . . ?
C16 C15 N3 124.1(3) . . ?
C15 C16 C17 121.3(3) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C18 C17 C16 119.3(4) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 121.5(3) . . ?
C17 C18 Cl1 119.1(3) . . ?
C19 C18 Cl1 119.4(3) . . ?
C18 C19 C20 118.5(3) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 H19 120.7 . . ?
C15 C20 C19 121.9(3) . . ?
C15 C20 Cl2 119.8(3) . . ?
C19 C20 Cl2 118.2(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
C13 N1 N2 C14 176.4(3) . . . . ?
C9B O1 C1 C2 164.8(7) . . . . ?
C9A O1 C1 C2 -158.4(5) . . . . ?
C9B O1 C1 C6 -14.4(9) . . . . ?
C9A O1 C1 C6 22.4(6) . . . . ?
O1 C1 C2 C3 -178.8(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C5 1.4(7) . . . . ?
C3 C4 C5 C6 -1.5(6) . . . . ?
O1 C1 C6 C5 178.8(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
O1 C1 C6 C7 0.4(5) . . . . ?
C2 C1 C6 C7 -178.8(3) . . . . ?
C4 C5 C6 C1 1.0(5) . . . . ?
C4 C5 C6 C7 179.3(4) . . . . ?
C1 C6 C7 C8 -3.1(5) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C6 C7 C8 C13 177.0(3) . . . . ?
C6 C7 C8 C9A -15.2(6) . . . . ?
C6 C7 C8 C9B 15.9(7) . . . . ?
C1 O1 C9A C8 -40.3(8) . . . . ?
C1 O1 C9A C10A -164.1(5) . . . . ?
C7 C8 C9A O1 36.3(8) . . . . ?
C13 C8 C9A O1 -155.3(4) . . . . ?
C7 C8 C9A C10A 156.8(6) . . . . ?
C13 C8 C9A C10A -34.8(9) . . . . ?
O1 C9A C10A C11A -174.9(5) . . . . ?
C8 C9A C10A C11A 59.9(9) . . . . ?
C9A C10A C11A C12A -68.9(12) . . . . ?
C10A C11A C12A C13 49.9(14) . . . . ?
C1 O1 C9B C8 27.8(12) . . . . ?
C1 O1 C9B C10B 156.3(8) . . . . ?
C7 C8 C9B O1 -28.2(11) . . . . ?
C13 C8 C9B O1 169.6(6) . . . . ?
C7 C8 C9B C10B -159.6(8) . . . . ?
C13 C8 C9B C10B 38.2(11) . . . . ?
O1 C9B C10B C11B 166.6(9) . . . . ?
C8 C9B C10B C11B -61.0(13) . . . . ?
C9B C10B C11B C12B 68.2(17) . . . . ?
C10B C11B C12B C13 -51.7(19) . . . . ?
N2 N1 C13 C8 -179.8(3) . . . . ?
N2 N1 C13 C12A -3.3(9) . . . . ?
N2 N1 C13 C12B 3.8(12) . . . . ?
C7 C8 C13 N1 -0.3(5) . . . . ?
C9A C8 C13 N1 -167.6(5) . . . . ?
C9B C8 C13 N1 160.1(6) . . . . ?
C7 C8 C13 C12A -176.9(8) . . . . ?
C9A C8 C13 C12A 15.8(10) . . . . ?
C7 C8 C13 C12B 176.4(11) . . . . ?
C9B C8 C13 C12B -23.3(12) . . . . ?
C11A C12A C13 N1 160.2(7) . . . . ?
C11A C12A C13 C8 -23.3(14) . . . . ?
C11B C12B C13 N1 -154.0(9) . . . . ?
C11B C12B C13 C8 29.7(18) . . . . ?
C15 N3 C14 N2 177.5(3) . . . . ?
C15 N3 C14 S1 -5.5(6) . . . . ?
N1 N2 C14 N3 3.6(5) . . . . ?
N1 N2 C14 S1 -173.8(2) . . . . ?
C14 N3 C15 C20 170.1(3) . . . . ?
C14 N3 C15 C16 -12.9(6) . . . . ?
C20 C15 C16 C17 -2.1(5) . . . . ?
N3 C15 C16 C17 -179.1(3) . . . . ?
C15 C16 C17 C18 -0.5(6) . . . . ?
C16 C17 C18 C19 2.8(6) . . . . ?
C16 C17 C18 Cl1 -177.6(3) . . . . ?
C17 C18 C19 C20 -2.5(5) . . . . ?
Cl1 C18 C19 C20 177.9(3) . . . . ?
C16 C15 C20 C19 2.5(5) . . . . ?
N3 C15 C20 C19 179.7(3) . . . . ?
C16 C15 C20 Cl2 -177.4(3) . . . . ?
N3 C15 C20 Cl2 -0.2(4) . . . . ?
C18 C19 C20 C15 -0.3(5) . . . . ?
C18 C19 C20 Cl2 179.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A S1 0.86 2.86 3.610(3) 146.8 2_776
N3 H3A Cl2 0.86 2.44 2.929(3) 116.5 .
N3 H3A N1 0.86 2.12 2.585(3) 113.2 .
C10B H10C S1 0.97 3.05 3.834(13) 139.3 1_545
C16 H16 S1 0.93 2.54 3.196(4) 128.2 .

_refine_diff_density_max         0.618
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.053

_shelxl_version_number           2014/6

