# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 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_3
_database_code_depnum_ccdc_archive 'CCDC 1018234'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H15 Cl3 N4 S'
_chemical_formula_sum            'C21 H15 Cl3 N4 S'
_chemical_formula_weight         461.78

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'
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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.1564(5)
_cell_length_b                   10.8019(6)
_cell_length_c                   12.5480(6)
_cell_angle_alpha                72.7980(10)
_cell_angle_beta                 69.2840(10)
_cell_angle_gamma                67.7280(10)
_cell_volume                     1055.33(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3695
_cell_measurement_theta_min      2.460
_cell_measurement_theta_max      27.310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9371
_exptl_absorpt_correction_T_max  0.9472
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5922
_diffrn_reflns_av_R_equivalents  0.0123
_diffrn_reflns_av_sigmaI/netI    0.0176
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3695
_reflns_number_gt                3030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0686P)²+0.7944P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3695
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1568
_refine_ls_wR_factor_gt          0.1502
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7021(4) -0.0052(3) 0.6538(3) 0.0552(7) Uani 1 1 d . . .
H10 H 0.7902 -0.0580 0.6844 0.066 Uiso 1 1 calc R . .
C2 C 0.7299(4) 0.0897(3) 0.5537(3) 0.0543(7) Uani 1 1 d . . .
H9 H 0.8328 0.1020 0.5200 0.065 Uiso 1 1 calc R . .
C3 C 0.6032(3) 0.1656(3) 0.5048(3) 0.0491(6) Uani 1 1 d . . .
H8 H 0.6192 0.2301 0.4374 0.059 Uiso 1 1 calc R . .
C4 C 0.4488(3) 0.1449(3) 0.5576(2) 0.0408(6) Uani 1 1 d . . .
C5 C 0.3052(3) 0.2127(3) 0.5155(2) 0.0414(6) Uani 1 1 d . . .
C6 C 0.1567(3) 0.1910(3) 0.5760(2) 0.0460(6) Uani 1 1 d . . .
C7 C 0.1345(3) 0.0985(3) 0.6841(2) 0.0483(6) Uani 1 1 d . . .
C8 C -0.0163(4) 0.0769(4) 0.7488(3) 0.0624(8) Uani 1 1 d . . .
H3 H -0.1103 0.1263 0.7240 0.075 Uiso 1 1 calc R . .
C9 C -0.0229(5) -0.0174(4) 0.8484(3) 0.0758(10) Uani 1 1 d . . .
H2 H -0.1211 -0.0348 0.8927 0.091 Uiso 1 1 calc R . .
C10 C 0.1207(5) -0.0876(4) 0.8828(3) 0.0782(11) Uani 1 1 d . . .
H1 H 0.1149 -0.1531 0.9505 0.094 Uiso 1 1 calc R . .
C11 C 0.2726(3) 0.0252(3) 0.7267(2) 0.0474(6) Uani 1 1 d . . .
C12 C 0.4311(3) 0.0486(3) 0.6628(2) 0.0436(6) Uani 1 1 d . . .
C13 C 0.1176(3) 0.3330(3) 0.4216(2) 0.0484(6) Uani 1 1 d . . .
C14 C 0.0399(3) 0.4254(3) 0.3327(3) 0.0550(7) Uani 1 1 d . . .
C15 C 0.0579(4) 0.5472(3) 0.2658(3) 0.0667(9) Uani 1 1 d . . .
H15 H 0.1291 0.5872 0.2699 0.080 Uiso 1 1 calc R . .
C16 C -0.0437(5) 0.6054(4) 0.1900(4) 0.0847(12) Uani 1 1 d . . .
H16 H -0.0467 0.6879 0.1385 0.102 Uiso 1 1 calc R . .
C17 C -0.1344(5) 0.5293(5) 0.2004(4) 0.0985(15) Uani 1 1 d . . .
H17 H -0.2083 0.5530 0.1571 0.118 Uiso 1 1 calc R . .
C18 C 0.4036(3) 0.3432(3) 0.3120(2) 0.0480(6) Uani 1 1 d . . .
H18A H 0.3624 0.3663 0.2450 0.058 Uiso 1 1 calc R . .
H18B H 0.5013 0.2649 0.3018 0.058 Uiso 1 1 calc R . .
C19 C 0.4507(4) 0.4593(3) 0.3145(3) 0.0618(8) Uani 1 1 d . . .
H19 H 0.5338 0.4826 0.2519 0.074 Uiso 1 1 calc R . .
C20 C 0.3880(6) 0.5307(4) 0.3947(5) 0.0891(12) Uani 1 1 d . . .
H20A H 0.3045 0.5113 0.4591 0.107 Uiso 1 1 calc R . .
H20B H 0.4260 0.6018 0.3883 0.107 Uiso 1 1 calc R . .
C21 C 0.5253(5) 0.7837(4) -0.0150(3) 0.0720(10) Uani 1 1 d . . .
H21 H 0.4815 0.8577 -0.0737 0.086 Uiso 1 1 calc R . .
Cl1 Cl 0.4245(2) 0.66247(14) 0.02385(13) 0.1278(6) Uani 1 1 d . . .
Cl2 Cl 0.48982(17) 0.85043(12) 0.10630(9) 0.1008(4) Uani 1 1 d . . .
Cl3 Cl 0.73407(16) 0.71381(16) -0.07282(10) 0.1209(5) Uani 1 1 d . . .
N1 N 0.5583(3) -0.0260(2) 0.7091(2) 0.0498(6) Uani 1 1 d . . .
N2 N 0.2646(3) -0.0679(3) 0.8260(2) 0.0634(7) Uani 1 1 d . . .
N3 N 0.2803(3) 0.3043(2) 0.41489(18) 0.0432(5) Uani 1 1 d . . .
N4 N 0.0392(3) 0.2662(3) 0.5172(2) 0.0524(6) Uani 1 1 d . . .
S1 S -0.10155(13) 0.38332(14) 0.30165(9) 0.0929(4) 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
C1 N1 1.324(4) . ?
C1 C2 1.379(4) . ?
C1 H10 0.9300 . ?
C2 C3 1.371(4) . ?
C2 H9 0.9300 . ?
C3 C4 1.406(4) . ?
C3 H8 0.9300 . ?
C4 C12 1.420(4) . ?
C4 C5 1.441(4) . ?
C5 C6 1.374(4) . ?
C5 N3 1.385(3) . ?
C6 N4 1.380(3) . ?
C6 C7 1.427(4) . ?
C7 C8 1.400(4) . ?
C7 C11 1.407(4) . ?
C8 C9 1.358(5) . ?
C8 H3 0.9300 . ?
C9 C10 1.394(5) . ?
C9 H2 0.9300 . ?
C10 N2 1.323(5) . ?
C10 H1 0.9300 . ?
C11 N2 1.349(4) . ?
C11 C12 1.465(4) . ?
C12 N1 1.354(3) . ?
C13 N4 1.322(4) . ?
C13 N3 1.378(3) . ?
C13 C14 1.453(4) . ?
C14 C15 1.370(5) . ?
C14 S1 1.716(3) . ?
C15 C16 1.413(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.327(6) . ?
C16 H16 0.9300 . ?
C17 S1 1.708(4) . ?
C17 H17 0.9300 . ?
C18 N3 1.458(3) . ?
C18 C19 1.484(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.286(5) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9300 . ?
C20 H20B 0.9300 . ?
C21 Cl3 1.732(4) . ?
C21 Cl1 1.739(4) . ?
C21 Cl2 1.750(3) . ?
C21 H21 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.3(3) . . ?
N1 C1 H10 117.8 . . ?
C2 C1 H10 117.8 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H9 120.6 . . ?
C1 C2 H9 120.6 . . ?
C2 C3 C4 119.4(3) . . ?
C2 C3 H8 120.3 . . ?
C4 C3 H8 120.3 . . ?
C3 C4 C12 117.4(2) . . ?
C3 C4 C5 126.3(2) . . ?
C12 C4 C5 116.4(2) . . ?
C6 C5 N3 105.7(2) . . ?
C6 C5 C4 122.3(2) . . ?
N3 C5 C4 132.1(2) . . ?
C5 C6 N4 111.3(2) . . ?
C5 C6 C7 122.3(2) . . ?
N4 C6 C7 126.4(2) . . ?
C8 C7 C11 118.8(3) . . ?
C8 C7 C6 123.4(3) . . ?
C11 C7 C6 117.7(2) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H3 120.6 . . ?
C7 C8 H3 120.6 . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H2 120.7 . . ?
C10 C9 H2 120.7 . . ?
N2 C10 C9 124.6(3) . . ?
N2 C10 H1 117.7 . . ?
C9 C10 H1 117.7 . . ?
N2 C11 C7 121.9(3) . . ?
N2 C11 C12 117.9(3) . . ?
C7 C11 C12 120.2(2) . . ?
N1 C12 C4 122.2(2) . . ?
N1 C12 C11 116.7(2) . . ?
C4 C12 C11 121.1(2) . . ?
N4 C13 N3 112.9(2) . . ?
N4 C13 C14 123.2(3) . . ?
N3 C13 C14 123.9(3) . . ?
C15 C14 C13 130.9(3) . . ?
C15 C14 S1 110.8(2) . . ?
C13 C14 S1 118.2(2) . . ?
C14 C15 C16 112.6(3) . . ?
C14 C15 H15 123.7 . . ?
C16 C15 H15 123.7 . . ?
C17 C16 C15 112.4(4) . . ?
C17 C16 H16 123.8 . . ?
C15 C16 H16 123.8 . . ?
C16 C17 S1 113.0(3) . . ?
C16 C17 H17 123.5 . . ?
S1 C17 H17 123.5 . . ?
N3 C18 C19 115.1(2) . . ?
N3 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
N3 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 126.4(3) . . ?
C20 C19 H19 116.8 . . ?
C18 C19 H19 116.8 . . ?
C19 C20 H20A 120.0 . . ?
C19 C20 H20B 120.0 . . ?
H20A C20 H20B 120.0 . . ?
Cl3 C21 Cl1 110.9(2) . . ?
Cl3 C21 Cl2 110.0(2) . . ?
Cl1 C21 Cl2 109.8(2) . . ?
Cl3 C21 H21 108.7 . . ?
Cl1 C21 H21 108.7 . . ?
Cl2 C21 H21 108.7 . . ?
C1 N1 C12 117.8(2) . . ?
C10 N2 C11 117.2(3) . . ?
C13 N3 C5 105.9(2) . . ?
C13 N3 C18 125.2(2) . . ?
C5 N3 C18 127.9(2) . . ?
C13 N4 C6 104.3(2) . . ?
C17 S1 C14 91.15(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -2.2(5) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C2 C3 C4 C12 2.4(4) . . . . ?
C2 C3 C4 C5 -177.9(3) . . . . ?
C3 C4 C5 C6 -176.7(3) . . . . ?
C12 C4 C5 C6 3.0(4) . . . . ?
C3 C4 C5 N3 4.7(4) . . . . ?
C12 C4 C5 N3 -175.6(2) . . . . ?
N3 C5 C6 N4 -0.3(3) . . . . ?
C4 C5 C6 N4 -179.2(2) . . . . ?
N3 C5 C6 C7 178.2(2) . . . . ?
C4 C5 C6 C7 -0.7(4) . . . . ?
C5 C6 C7 C8 178.4(3) . . . . ?
N4 C6 C7 C8 -3.3(5) . . . . ?
C5 C6 C7 C11 -2.0(4) . . . . ?
N4 C6 C7 C11 176.3(3) . . . . ?
C11 C7 C8 C9 -2.2(5) . . . . ?
C6 C7 C8 C9 177.4(3) . . . . ?
C7 C8 C9 C10 0.8(6) . . . . ?
C8 C9 C10 N2 1.1(6) . . . . ?
C8 C7 C11 N2 2.0(4) . . . . ?
C6 C7 C11 N2 -177.6(3) . . . . ?
C8 C7 C11 C12 -178.1(3) . . . . ?
C6 C7 C11 C12 2.3(4) . . . . ?
C3 C4 C12 N1 -3.0(4) . . . . ?
C5 C4 C12 N1 177.3(2) . . . . ?
C3 C4 C12 C11 177.1(2) . . . . ?
C5 C4 C12 C11 -2.7(3) . . . . ?
N2 C11 C12 N1 0.0(4) . . . . ?
C7 C11 C12 N1 -179.9(2) . . . . ?
N2 C11 C12 C4 180.0(2) . . . . ?
C7 C11 C12 C4 0.1(4) . . . . ?
N4 C13 C14 C15 141.7(4) . . . . ?
N3 C13 C14 C15 -39.0(5) . . . . ?
N4 C13 C14 S1 -37.5(4) . . . . ?
N3 C13 C14 S1 141.7(2) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
S1 C14 C15 C16 0.1(4) . . . . ?
C14 C15 C16 C17 0.1(5) . . . . ?
C15 C16 C17 S1 -0.3(6) . . . . ?
N3 C18 C19 C20 -3.6(5) . . . . ?
C2 C1 N1 C12 1.6(4) . . . . ?
C4 C12 N1 C1 1.0(4) . . . . ?
C11 C12 N1 C1 -179.0(2) . . . . ?
C9 C10 N2 C11 -1.3(6) . . . . ?
C7 C11 N2 C10 -0.2(5) . . . . ?
C12 C11 N2 C10 179.9(3) . . . . ?
N4 C13 N3 C5 -0.6(3) . . . . ?
C14 C13 N3 C5 -179.9(3) . . . . ?
N4 C13 N3 C18 168.7(2) . . . . ?
C14 C13 N3 C18 -10.6(4) . . . . ?
C6 C5 N3 C13 0.5(3) . . . . ?
C4 C5 N3 C13 179.3(3) . . . . ?
C6 C5 N3 C18 -168.3(2) . . . . ?
C4 C5 N3 C18 10.4(4) . . . . ?
C19 C18 N3 C13 104.5(3) . . . . ?
C19 C18 N3 C5 -88.7(3) . . . . ?
N3 C13 N4 C6 0.4(3) . . . . ?
C14 C13 N4 C6 179.7(3) . . . . ?
C5 C6 N4 C13 0.0(3) . . . . ?
C7 C6 N4 C13 -178.5(3) . . . . ?
C16 C17 S1 C14 0.2(4) . . . . ?
C15 C14 S1 C17 -0.2(3) . . . . ?
C13 C14 S1 C17 179.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.775
_refine_diff_density_min         -0.804
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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 1018235'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H18 N4 S'
_chemical_formula_sum            'C21 H18 N4 S'
_chemical_formula_weight         358.45

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

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.7125(19)
_cell_length_b                   9.9228(19)
_cell_length_c                   11.205(2)
_cell_angle_alpha                114.272(2)
_cell_angle_beta                 109.020(3)
_cell_angle_gamma                97.147(3)
_cell_volume                     887.9(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3088
_cell_measurement_theta_min      2.195
_cell_measurement_theta_max      28.333

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.194
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9770
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6551
_diffrn_reflns_av_R_equivalents  0.0332
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3088
_reflns_number_gt                2633
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0792P)²+0.2490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3088
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1391
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.2222(3) 0.1558(2) 0.3858(2) 0.0477(5) Uani 1 1 d . . .
H1 H -0.2654 0.0865 0.4091 0.057 Uiso 1 1 calc R . .
C2 C -0.1032(2) 0.1301(2) 0.3450(2) 0.0459(5) Uani 1 1 d . . .
H2 H -0.0678 0.0463 0.3420 0.055 Uiso 1 1 calc R . .
C3 C -0.0394(2) 0.2300(2) 0.3095(2) 0.0402(4) Uani 1 1 d . . .
H3 H 0.0402 0.2146 0.2816 0.048 Uiso 1 1 calc R . .
C4 C -0.0938(2) 0.3561(2) 0.31490(18) 0.0331(4) Uani 1 1 d . . .
C5 C -0.0379(2) 0.4722(2) 0.28201(18) 0.0320(4) Uani 1 1 d . . .
C6 C -0.0984(2) 0.5931(2) 0.29195(18) 0.0336(4) Uani 1 1 d . . .
C7 C -0.2204(2) 0.6117(2) 0.33558(18) 0.0341(4) Uani 1 1 d . . .
C8 C -0.2847(2) 0.7324(2) 0.3473(2) 0.0423(5) Uani 1 1 d . . .
H8 H -0.2530 0.8032 0.3200 0.051 Uiso 1 1 calc R . .
C9 C -0.3942(2) 0.7458(2) 0.3990(2) 0.0440(5) Uani 1 1 d . . .
H9 H -0.4386 0.8251 0.4070 0.053 Uiso 1 1 calc R . .
C10 C -0.4383(2) 0.6381(2) 0.4396(2) 0.0437(5) Uani 1 1 d . . .
H10 H -0.5101 0.6503 0.4784 0.052 Uiso 1 1 calc R . .
C11 C -0.2762(2) 0.5041(2) 0.37369(18) 0.0348(4) Uani 1 1 d . . .
C12 C -0.2147(2) 0.3739(2) 0.35967(18) 0.0349(4) Uani 1 1 d . . .
C13 C 0.0809(2) 0.6275(2) 0.22787(18) 0.0343(4) Uani 1 1 d . . .
C14 C 0.1901(2) 0.6969(2) 0.1899(2) 0.0379(4) Uani 1 1 d . . .
C15 C 0.2477(2) 0.6311(3) 0.0886(2) 0.0424(5) Uani 1 1 d . . .
H15 H 0.2247 0.5250 0.0309 0.051 Uiso 1 1 calc R . .
C16 C 0.3448(3) 0.7438(3) 0.0837(3) 0.0605(7) Uani 1 1 d . . .
H16 H 0.3933 0.7201 0.0217 0.073 Uiso 1 1 calc R . .
C17 C 0.3608(3) 0.8891(3) 0.1773(3) 0.0645(7) Uani 1 1 d . . .
H17 H 0.4220 0.9769 0.1880 0.077 Uiso 1 1 calc R . .
C18 C 0.1817(2) 0.4018(2) 0.21670(19) 0.0358(4) Uani 1 1 d . . .
H18A H 0.2145 0.3740 0.2927 0.043 Uiso 1 1 calc R . .
H18B H 0.2716 0.4630 0.2219 0.043 Uiso 1 1 calc R . .
C19 C 0.1073(2) 0.2548(2) 0.0717(2) 0.0413(5) Uani 1 1 d . . .
H19A H 0.0094 0.2016 0.0606 0.050 Uiso 1 1 calc R . .
H19B H 0.0884 0.2828 -0.0043 0.050 Uiso 1 1 calc R . .
C20 C 0.2036(3) 0.1457(3) 0.0548(3) 0.0603(6) Uani 1 1 d . . .
H20A H 0.2307 0.1261 0.1362 0.072 Uiso 1 1 calc R . .
H20B H 0.1429 0.0477 -0.0315 0.072 Uiso 1 1 calc R . .
C21 C 0.3476(3) 0.2052(4) 0.0450(4) 0.0773(8) Uani 1 1 d . . .
H21A H 0.3225 0.2300 -0.0322 0.116 Uiso 1 1 calc R . .
H21B H 0.3988 0.1271 0.0271 0.116 Uiso 1 1 calc R . .
H21C H 0.4134 0.2966 0.1340 0.116 Uiso 1 1 calc R . .
N1 N -0.27766(19) 0.2726(2) 0.39344(18) 0.0442(4) Uani 1 1 d . . .
N2 N -0.38378(18) 0.5198(2) 0.42615(17) 0.0413(4) Uani 1 1 d . . .
N3 N 0.07887(17) 0.49527(17) 0.24047(15) 0.0325(4) Uani 1 1 d . . .
N4 N -0.02378(18) 0.68963(18) 0.25845(16) 0.0363(4) Uani 1 1 d . . .
S1 S 0.25619(7) 0.89463(6) 0.27412(7) 0.0545(2) 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
C1 N1 1.321(3) . ?
C1 C2 1.390(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.404(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.423(3) . ?
C4 C5 1.443(2) . ?
C5 C6 1.381(3) . ?
C5 N3 1.387(2) . ?
C6 N4 1.372(2) . ?
C6 C7 1.427(3) . ?
C7 C8 1.397(3) . ?
C7 C11 1.413(3) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.320(3) . ?
C10 H10 0.9300 . ?
C11 N2 1.351(2) . ?
C11 C12 1.462(3) . ?
C12 N1 1.356(2) . ?
C13 N4 1.319(2) . ?
C13 N3 1.375(2) . ?
C13 C14 1.461(2) . ?
C14 C15 1.386(3) . ?
C14 S1 1.710(2) . ?
C15 C16 1.401(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.341(4) . ?
C16 H16 0.9300 . ?
C17 S1 1.702(3) . ?
C17 H17 0.9300 . ?
C18 N3 1.460(2) . ?
C18 C19 1.521(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.511(3) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.505(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
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
N1 C1 C2 124.05(19) . . ?
N1 C1 H1 118.0 . . ?
C2 C1 H1 118.0 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.00(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 117.24(17) . . ?
C3 C4 C5 126.66(18) . . ?
C12 C4 C5 116.09(17) . . ?
C6 C5 N3 105.36(15) . . ?
C6 C5 C4 122.29(17) . . ?
N3 C5 C4 132.33(17) . . ?
N4 C6 C5 111.22(16) . . ?
N4 C6 C7 126.56(17) . . ?
C5 C6 C7 122.20(17) . . ?
C8 C7 C11 118.07(17) . . ?
C8 C7 C6 124.02(17) . . ?
C11 C7 C6 117.88(17) . . ?
C9 C8 C7 119.53(19) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C10 118.62(19) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
N2 C10 C9 123.68(19) . . ?
N2 C10 H10 118.2 . . ?
C9 C10 H10 118.2 . . ?
N2 C11 C7 121.68(18) . . ?
N2 C11 C12 118.49(17) . . ?
C7 C11 C12 119.81(17) . . ?
N1 C12 C4 121.94(18) . . ?
N1 C12 C11 116.41(17) . . ?
C4 C12 C11 121.65(16) . . ?
N4 C13 N3 112.94(15) . . ?
N4 C13 C14 122.77(17) . . ?
N3 C13 C14 124.26(17) . . ?
C15 C14 C13 131.54(18) . . ?
C15 C14 S1 110.83(15) . . ?
C13 C14 S1 117.53(14) . . ?
C14 C15 C16 111.9(2) . . ?
C14 C15 H15 124.0 . . ?
C16 C15 H15 124.0 . . ?
C17 C16 C15 113.2(2) . . ?
C17 C16 H16 123.4 . . ?
C15 C16 H16 123.4 . . ?
C16 C17 S1 112.30(17) . . ?
C16 C17 H17 123.9 . . ?
S1 C17 H17 123.9 . . ?
N3 C18 C19 112.46(15) . . ?
N3 C18 H18A 109.1 . . ?
C19 C18 H18A 109.1 . . ?
N3 C18 H18B 109.1 . . ?
C19 C18 H18B 109.1 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 112.96(18) . . ?
C20 C19 H19A 109.0 . . ?
C18 C19 H19A 109.0 . . ?
C20 C19 H19B 109.0 . . ?
C18 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C21 C20 C19 114.0(2) . . ?
C21 C20 H20A 108.7 . . ?
C19 C20 H20A 108.7 . . ?
C21 C20 H20B 108.7 . . ?
C19 C20 H20B 108.7 . . ?
H20A C20 H20B 107.6 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 N1 C12 118.11(18) . . ?
C10 N2 C11 118.32(17) . . ?
C13 N3 C5 105.92(15) . . ?
C13 N3 C18 126.14(15) . . ?
C5 N3 C18 127.93(15) . . ?
C13 N4 C6 104.56(15) . . ?
C17 S1 C14 91.73(12) . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.380
_refine_diff_density_rms         0.049
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_5
_database_code_depnum_ccdc_archive 'CCDC 1018236'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 Br Cl3 N4 S'
_chemical_formula_sum            'C22 H18 Br Cl3 N4 S'
_chemical_formula_weight         556.72

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'
Br Br -0.2901 2.4595 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.276(3)
_cell_length_b                   10.410(3)
_cell_length_c                   13.153(4)
_cell_angle_alpha                107.382(5)
_cell_angle_beta                 104.667(5)
_cell_angle_gamma                97.372(5)
_cell_volume                     1143.6(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3915
_cell_measurement_theta_min      2.191
_cell_measurement_theta_max      28.239

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    2.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7734
_exptl_absorpt_correction_T_max  0.8057
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6035
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3915
_reflns_number_gt                2946
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0845P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3915
_refine_ls_number_parameters     309
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.1579
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.07266(6) 0.78189(5) 0.66271(4) 0.0451(2) Uani 1 1 d . . .
C1 C 0.3421(6) -0.0843(5) 0.1097(4) 0.0398(12) Uani 1 1 d . . .
H1 H 0.3271 -0.1501 0.0400 0.048 Uiso 1 1 calc R . .
C2 C 0.2444(6) 0.0050(5) 0.1178(4) 0.0406(12) Uani 1 1 d . . .
H2 H 0.1643 -0.0035 0.0554 0.049 Uiso 1 1 calc R . .
C3 C 0.2664(5) 0.1064(5) 0.2183(4) 0.0334(11) Uani 1 1 d . . .
H3 H 0.2027 0.1684 0.2253 0.040 Uiso 1 1 calc R . .
C4 C 0.3868(5) 0.1140(4) 0.3101(3) 0.0250(9) Uani 1 1 d . . .
C5 C 0.4218(5) 0.2162(4) 0.4180(3) 0.0237(9) Uani 1 1 d . . .
C6 C 0.5421(5) 0.2205(4) 0.5064(3) 0.0245(9) Uani 1 1 d . . .
C7 C 0.6389(5) 0.1256(4) 0.4969(3) 0.0237(9) Uani 1 1 d . . .
C8 C 0.7655(5) 0.1217(4) 0.5805(3) 0.0278(10) Uani 1 1 d . . .
H8 H 0.7963 0.1896 0.6512 0.033 Uiso 1 1 calc R . .
C9 C 0.8429(5) 0.0206(5) 0.5594(4) 0.0306(10) Uani 1 1 d . . .
H9 H 0.9268 0.0184 0.6148 0.037 Uiso 1 1 calc R . .
C10 C 0.7954(5) -0.0807(4) 0.4532(4) 0.0310(10) Uani 1 1 d . . .
H10 H 0.8468 -0.1521 0.4405 0.037 Uiso 1 1 calc R . .
C11 C 0.6033(5) 0.0196(4) 0.3896(3) 0.0253(9) Uani 1 1 d . . .
C12 C 0.4785(5) 0.0175(4) 0.2969(3) 0.0259(9) Uani 1 1 d . . .
C13 C 0.4208(5) 0.3856(4) 0.5568(3) 0.0247(9) Uani 1 1 d . . .
C14 C 0.3736(5) 0.5046(4) 0.6205(3) 0.0257(9) Uani 1 1 d . . .
C15 C 0.4402(5) 0.6053(4) 0.7227(4) 0.0316(10) Uani 1 1 d . . .
H15 H 0.5345 0.6086 0.7707 0.038 Uiso 1 1 calc R . .
C16 C 0.3520(5) 0.7039(5) 0.7484(4) 0.0334(11) Uani 1 1 d . . .
H16 H 0.3817 0.7790 0.8149 0.040 Uiso 1 1 calc R . .
C17 C 0.2220(5) 0.6780(4) 0.6674(4) 0.0317(10) Uani 1 1 d . . .
C18 C 0.6329(5) 0.3716(4) 0.7142(3) 0.0261(9) Uani 1 1 d . . .
H18A H 0.6570 0.2904 0.7302 0.031 Uiso 1 1 calc R . .
H18B H 0.5753 0.4126 0.7626 0.031 Uiso 1 1 calc R . .
C19 C 0.7803(5) 0.4742(4) 0.7396(3) 0.0273(9) Uani 1 1 d . . .
H19A H 0.8381 0.4332 0.6914 0.033 Uiso 1 1 calc R . .
H19B H 0.7563 0.5555 0.7235 0.033 Uiso 1 1 calc R . .
C20 C 0.8766(6) 0.5165(5) 0.8601(4) 0.0393(12) Uani 1 1 d . . .
H20A H 0.8137 0.5452 0.9078 0.047 Uiso 1 1 calc R . .
H20B H 0.9109 0.4369 0.8731 0.047 Uiso 1 1 calc R . .
C21 C 1.0132(6) 0.6312(6) 0.8931(4) 0.0486(14) Uani 1 1 d . . .
H21A H 1.0763 0.6037 0.8464 0.073 Uiso 1 1 calc R . .
H21B H 1.0706 0.6516 0.9699 0.073 Uiso 1 1 calc R . .
H21C H 0.9801 0.7119 0.8839 0.073 Uiso 1 1 calc R . .
C22 C 0.7176(6) 0.7586(5) 0.1387(4) 0.0511(14) Uani 1 1 d D . .
H22 H 0.6753 0.8212 0.1893 0.077 Uiso 1 1 d R A .
N1 N 0.4561(4) -0.0822(4) 0.1952(3) 0.0335(9) Uani 1 1 d . . .
N2 N 0.6813(4) -0.0802(3) 0.3700(3) 0.0278(8) Uani 1 1 d . . .
N3 N 0.5386(4) 0.3303(3) 0.5969(3) 0.0229(8) Uani 1 1 d . . .
N4 N 0.3479(4) 0.3191(3) 0.4490(3) 0.0257(8) Uani 1 1 d . . .
S1 S 0.20000(13) 0.53142(11) 0.55533(9) 0.0322(3) Uani 1 1 d . . .
Cl1 Cl 0.7554(4) 0.6278(2) 0.1867(2) 0.0652(9) Uani 0.746(7) 1 d PD A 1
Cl2 Cl 0.8967(3) 0.8504(3) 0.13913(19) 0.0648(9) Uani 0.746(7) 1 d PD A 1
Cl3 Cl 0.5933(4) 0.7024(5) 0.0039(2) 0.0930(15) Uani 0.746(7) 1 d PD A 1
Cl1' Cl 0.764(3) 0.8580(11) 0.0733(17) 0.213(13) Uani 0.254(7) 1 d PD A 2
Cl2' Cl 0.5619(10) 0.6196(11) 0.0413(8) 0.092(4) Uani 0.254(7) 1 d PD . 2
Cl3' Cl 0.846(2) 0.687(2) 0.2034(11) 0.244(13) Uani 0.254(7) 1 d PD A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C17 1.864(5) . ?
C1 N1 1.326(6) . ?
C1 C2 1.379(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.371(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(6) . ?
C3 H3 0.9300 . ?
C4 C12 1.397(6) . ?
C4 C5 1.424(5) . ?
C5 N4 1.361(5) . ?
C5 C6 1.378(6) . ?
C6 N3 1.393(5) . ?
C6 C7 1.418(6) . ?
C7 C8 1.406(6) . ?
C7 C11 1.435(5) . ?
C8 C9 1.350(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.318(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.340(6) . ?
C11 C12 1.445(6) . ?
C12 N1 1.373(5) . ?
C13 N4 1.325(5) . ?
C13 N3 1.362(6) . ?
C13 C14 1.460(6) . ?
C14 C15 1.364(6) . ?
C14 S1 1.722(5) . ?
C15 C16 1.410(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.325(7) . ?
C16 H16 0.9300 . ?
C17 S1 1.722(4) . ?
C18 N3 1.467(5) . ?
C18 C19 1.517(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.506(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.498(7) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 Cl1' 1.612(11) . ?
C22 Cl3' 1.666(12) . ?
C22 Cl1 1.703(6) . ?
C22 Cl3 1.729(6) . ?
C22 Cl2' 1.800(8) . ?
C22 Cl2 1.805(6) . ?
C22 H22 0.9800 . ?
Cl2' Cl2' 2.390(19) 2_665 ?

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
N1 C1 C2 124.1(4) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 118.2(4) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C12 119.3(4) . . ?
C3 C4 C5 123.1(4) . . ?
C12 C4 C5 117.6(4) . . ?
N4 C5 C6 111.3(4) . . ?
N4 C5 C4 127.3(4) . . ?
C6 C5 C4 121.4(4) . . ?
C5 C6 N3 105.0(4) . . ?
C5 C6 C7 123.0(4) . . ?
N3 C6 C7 132.0(4) . . ?
C8 C7 C6 127.8(4) . . ?
C8 C7 C11 115.7(4) . . ?
C6 C7 C11 116.5(4) . . ?
C9 C8 C7 120.6(4) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.1(4) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 123.2(4) . . ?
N2 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
N2 C11 C7 122.8(4) . . ?
N2 C11 C12 117.2(4) . . ?
C7 C11 C12 120.0(4) . . ?
N1 C12 C4 121.7(4) . . ?
N1 C12 C11 116.9(4) . . ?
C4 C12 C11 121.5(4) . . ?
N4 C13 N3 112.6(4) . . ?
N4 C13 C14 121.0(4) . . ?
N3 C13 C14 126.4(4) . . ?
C15 C14 C13 133.6(4) . . ?
C15 C14 S1 110.5(3) . . ?
C13 C14 S1 115.9(3) . . ?
C14 C15 C16 113.3(4) . . ?
C14 C15 H15 123.3 . . ?
C16 C15 H15 123.3 . . ?
C17 C16 C15 112.5(4) . . ?
C17 C16 H16 123.7 . . ?
C15 C16 H16 123.7 . . ?
C16 C17 S1 112.6(3) . . ?
C16 C17 Br1 127.7(3) . . ?
S1 C17 Br1 119.7(3) . . ?
N3 C18 C19 112.0(3) . . ?
N3 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N3 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 111.8(3) . . ?
C20 C19 H19A 109.3 . . ?
C18 C19 H19A 109.3 . . ?
C20 C19 H19B 109.3 . . ?
C18 C19 H19B 109.3 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 113.7(4) . . ?
C21 C20 H20A 108.8 . . ?
C19 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C19 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1' C22 Cl3' 121.3(9) . . ?
Cl1' C22 Cl1 147.4(8) . . ?
Cl3' C22 Cl1 31.3(9) . . ?
Cl1' C22 Cl3 70.0(8) . . ?
Cl3' C22 Cl3 132.0(6) . . ?
Cl1 C22 Cl3 113.4(3) . . ?
Cl1' C22 Cl2' 107.9(8) . . ?
Cl3' C22 Cl2' 106.8(7) . . ?
Cl1 C22 Cl2' 79.3(5) . . ?
Cl3 C22 Cl2' 38.1(4) . . ?
Cl1' C22 Cl2 45.9(9) . . ?
Cl3' C22 Cl2 76.9(10) . . ?
Cl1 C22 Cl2 107.3(3) . . ?
Cl3 C22 Cl2 108.0(3) . . ?
Cl2' C22 Cl2 137.5(5) . . ?
Cl1' C22 H22 98.9 . . ?
Cl3' C22 H22 113.6 . . ?
Cl1 C22 H22 109.3 . . ?
Cl3 C22 H22 109.4 . . ?
Cl2' C22 H22 107.4 . . ?
Cl2 C22 H22 109.4 . . ?
C1 N1 C12 117.1(4) . . ?
C10 N2 C11 118.4(4) . . ?
C13 N3 C6 106.2(3) . . ?
C13 N3 C18 126.2(3) . . ?
C6 N3 C18 127.4(4) . . ?
C13 N4 C5 104.9(4) . . ?
C14 S1 C17 91.1(2) . . ?
C22 Cl2' Cl2' 151.7(10) . 2_665 ?

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
N1 C1 C2 C3 2.2(8) . . . . ?
C1 C2 C3 C4 -0.9(7) . . . . ?
C2 C3 C4 C12 -1.1(6) . . . . ?
C2 C3 C4 C5 178.9(4) . . . . ?
C3 C4 C5 N4 0.0(6) . . . . ?
C12 C4 C5 N4 -180.0(4) . . . . ?
C3 C4 C5 C6 -179.8(4) . . . . ?
C12 C4 C5 C6 0.2(6) . . . . ?
N4 C5 C6 N3 1.4(4) . . . . ?
C4 C5 C6 N3 -178.7(3) . . . . ?
N4 C5 C6 C7 -179.6(4) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
C5 C6 C7 C8 178.9(4) . . . . ?
N3 C6 C7 C8 -2.5(7) . . . . ?
C5 C6 C7 C11 -1.7(6) . . . . ?
N3 C6 C7 C11 177.0(4) . . . . ?
C6 C7 C8 C9 177.3(4) . . . . ?
C11 C7 C8 C9 -2.2(6) . . . . ?
C7 C8 C9 C10 -0.1(6) . . . . ?
C8 C9 C10 N2 2.7(7) . . . . ?
C8 C7 C11 N2 2.4(6) . . . . ?
C6 C7 C11 N2 -177.2(4) . . . . ?
C8 C7 C11 C12 -177.8(4) . . . . ?
C6 C7 C11 C12 2.6(6) . . . . ?
C3 C4 C12 N1 2.0(6) . . . . ?
C5 C4 C12 N1 -178.0(3) . . . . ?
C3 C4 C12 C11 -179.1(4) . . . . ?
C5 C4 C12 C11 0.8(6) . . . . ?
N2 C11 C12 N1 -3.6(5) . . . . ?
C7 C11 C12 N1 176.6(3) . . . . ?
N2 C11 C12 C4 177.5(4) . . . . ?
C7 C11 C12 C4 -2.3(6) . . . . ?
N4 C13 C14 C15 -166.1(4) . . . . ?
N3 C13 C14 C15 13.9(7) . . . . ?
N4 C13 C14 S1 11.8(5) . . . . ?
N3 C13 C14 S1 -168.2(3) . . . . ?
C13 C14 C15 C16 177.9(4) . . . . ?
S1 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 0.0(6) . . . . ?
C15 C16 C17 S1 0.1(5) . . . . ?
C15 C16 C17 Br1 -178.3(3) . . . . ?
N3 C18 C19 C20 179.9(4) . . . . ?
C18 C19 C20 C21 -172.4(4) . . . . ?
C2 C1 N1 C12 -1.3(7) . . . . ?
C4 C12 N1 C1 -0.8(6) . . . . ?
C11 C12 N1 C1 -179.7(4) . . . . ?
C9 C10 N2 C11 -2.6(6) . . . . ?
C7 C11 N2 C10 0.0(6) . . . . ?
C12 C11 N2 C10 -179.9(4) . . . . ?
N4 C13 N3 C6 0.9(4) . . . . ?
C14 C13 N3 C6 -179.1(4) . . . . ?
N4 C13 N3 C18 -174.2(3) . . . . ?
C14 C13 N3 C18 5.8(6) . . . . ?
C5 C6 N3 C13 -1.4(4) . . . . ?
C7 C6 N3 C13 179.8(4) . . . . ?
C5 C6 N3 C18 173.6(4) . . . . ?
C7 C6 N3 C18 -5.2(7) . . . . ?
C19 C18 N3 C13 -96.1(5) . . . . ?
C19 C18 N3 C6 89.8(5) . . . . ?
N3 C13 N4 C5 0.0(4) . . . . ?
C14 C13 N4 C5 180.0(4) . . . . ?
C6 C5 N4 C13 -0.9(4) . . . . ?
C4 C5 N4 C13 179.3(4) . . . . ?
C15 C14 S1 C17 0.2(3) . . . . ?
C13 C14 S1 C17 -178.2(3) . . . . ?
C16 C17 S1 C14 -0.2(4) . . . . ?
Br1 C17 S1 C14 178.4(3) . . . . ?
Cl1' C22 Cl2' Cl2' 135.2(15) . . . 2_665 ?
Cl3' C22 Cl2' Cl2' 3.2(18) . . . 2_665 ?
Cl1 C22 Cl2' Cl2' -12.0(17) . . . 2_665 ?
Cl3 C22 Cl2' Cl2' 141.6(19) . . . 2_665 ?
Cl2 C22 Cl2' Cl2' 92(2) . . . 2_665 ?

_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.973
_refine_diff_density_max         0.846
_refine_diff_density_min         -0.847
_refine_diff_density_rms         0.105
####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1018237'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H23 N5 O S'
_chemical_formula_sum            'C26 H23 N5 O S'
_chemical_formula_weight         453.55

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   16.2940(16)
_cell_length_b                   7.7687(8)
_cell_length_c                   19.2718(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 116.931(6)
_cell_angle_gamma                90.00
_cell_volume                     2174.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3833
_cell_measurement_theta_min      2.726
_cell_measurement_theta_max      21.893

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             952
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_T_max  0.9823
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11804
_diffrn_reflns_av_R_equivalents  0.1293
_diffrn_reflns_av_sigmaI/netI    0.1205
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3833
_reflns_number_gt                2249
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL


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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0388P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3833
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0890
_refine_ls_R_factor_gt           0.0522
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1161
_refine_ls_goodness_of_fit_ref   0.850
_refine_ls_restrained_S_all      0.850
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.12810(16) 0.7409(4) 0.69910(14) 0.0850(9) Uani 1 1 d . . .
H1B H 0.1761 0.7771 0.7381 0.102 Uiso 1 1 d R . .
H1A H 0.1117 0.6827 0.7281 0.102 Uiso 1 1 d R . .
C1 C 0.0607(2) 0.5614(5) 0.9510(2) 0.0583(10) Uani 1 1 d . . .
H1 H 0.0028 0.5983 0.9432 0.070 Uiso 1 1 calc R . .
C2 C 0.0684(2) 0.4947(5) 0.88870(19) 0.0585(10) Uani 1 1 d . . .
H2 H 0.0174 0.4889 0.8401 0.070 Uiso 1 1 calc R . .
C3 C 0.1520(2) 0.4368(4) 0.89876(18) 0.0499(9) Uani 1 1 d . . .
H3 H 0.1585 0.3915 0.8568 0.060 Uiso 1 1 calc R . .
C4 C 0.22870(18) 0.4456(4) 0.97279(15) 0.0338(7) Uani 1 1 d . . .
C5 C 0.32068(18) 0.3875(4) 0.99348(15) 0.0315(7) Uani 1 1 d . . .
C6 C 0.39220(18) 0.4085(4) 1.06786(14) 0.0309(7) Uani 1 1 d . . .
C7 C 0.37907(19) 0.4922(4) 1.12825(15) 0.0328(7) Uani 1 1 d . . .
C8 C 0.4507(2) 0.5238(4) 1.20252(15) 0.0390(7) Uani 1 1 d . . .
H8 H 0.5099 0.4846 1.2159 0.047 Uiso 1 1 calc R . .
C9 C 0.4324(2) 0.6137(4) 1.25543(17) 0.0469(8) Uani 1 1 d . . .
H9 H 0.4789 0.6392 1.3048 0.056 Uiso 1 1 calc R . .
C10 C 0.3416(2) 0.6653(4) 1.23254(18) 0.0513(9) Uani 1 1 d . . .
H10 H 0.3293 0.7250 1.2686 0.062 Uiso 1 1 calc R . .
C11 C 0.29007(19) 0.5487(4) 1.11077(15) 0.0363(7) Uani 1 1 d . . .
C12 C 0.21398(19) 0.5222(4) 1.03292(16) 0.0372(7) Uani 1 1 d . . .
C13 C 0.45267(18) 0.2908(4) 1.00151(15) 0.0312(6) Uani 1 1 d . . .
C14 C 0.31407(19) 0.2538(4) 0.86944(14) 0.0362(7) Uani 1 1 d . . .
H14A H 0.2519 0.2173 0.8568 0.043 Uiso 1 1 calc R . .
H14B H 0.3465 0.1555 0.8628 0.043 Uiso 1 1 calc R . .
C15 C 0.3100(2) 0.3941(4) 0.81414(15) 0.0432(8) Uani 1 1 d . . .
H15A H 0.3709 0.4436 0.8320 0.052 Uiso 1 1 calc R . .
H15B H 0.2691 0.4843 0.8147 0.052 Uiso 1 1 calc R . .
C16 C 0.2762(2) 0.3295(5) 0.73073(16) 0.0569(9) Uani 1 1 d . . .
H16A H 0.2782 0.4243 0.6988 0.068 Uiso 1 1 calc R . .
H16B H 0.3184 0.2418 0.7304 0.068 Uiso 1 1 calc R . .
C17 C 0.1808(2) 0.2561(5) 0.6944(2) 0.0763(12) Uani 1 1 d . . .
H17A H 0.1779 0.1617 0.7254 0.114 Uiso 1 1 calc R . .
H17B H 0.1656 0.2161 0.6429 0.114 Uiso 1 1 calc R . .
H17C H 0.1378 0.3435 0.6917 0.114 Uiso 1 1 calc R . .
C18 C 0.52350(18) 0.2180(4) 0.98384(15) 0.0319(7) Uani 1 1 d . . .
C19 C 0.5261(2) 0.1641(4) 0.91800(16) 0.0435(8) Uani 1 1 d . . .
H19 H 0.4752 0.1665 0.8693 0.052 Uiso 1 1 calc R . .
C20 C 0.6128(2) 0.1045(4) 0.93018(16) 0.0429(8) Uani 1 1 d . . .
H20 H 0.6247 0.0628 0.8904 0.051 Uiso 1 1 calc R . .
C21 C 0.67830(19) 0.1132(4) 1.00614(16) 0.0346(7) Uani 1 1 d . . .
C22 C 0.77568(19) 0.0656(4) 1.03997(16) 0.0371(7) Uani 1 1 d . . .
C23 C 0.8133(2) -0.0098(4) 0.99552(19) 0.0530(9) Uani 1 1 d . . .
H23 H 0.7766 -0.0298 0.9428 0.064 Uiso 1 1 calc R . .
C24 C 0.9049(3) -0.0549(5) 1.0295(2) 0.0669(11) Uani 1 1 d . . .
H24 H 0.9278 -0.1049 0.9980 0.080 Uiso 1 1 calc R . .
C25 C 0.9263(2) 0.0426(5) 1.1460(2) 0.0640(10) Uani 1 1 d . . .
H25 H 0.9652 0.0626 1.1983 0.077 Uiso 1 1 calc R . .
C26 C 0.8358(2) 0.0923(4) 1.11804(18) 0.0516(9) Uani 1 1 d . . .
H26 H 0.8152 0.1431 1.1510 0.062 Uiso 1 1 calc R . .
N1 N 0.12979(18) 0.5771(4) 1.02177(15) 0.0512(7) Uani 1 1 d . . .
N2 N 0.27191(18) 0.6356(3) 1.16333(14) 0.0474(7) Uani 1 1 d . . .
N3 N 0.36072(14) 0.3099(3) 0.95149(12) 0.0320(5) Uani 1 1 d . . .
N4 N 0.47363(15) 0.3490(3) 1.07233(12) 0.0341(6) Uani 1 1 d . . .
N5 N 0.96259(19) -0.0320(4) 1.1038(2) 0.0661(9) Uani 1 1 d . . .
S1 S 0.63052(5) 0.19674(10) 1.06268(4) 0.0387(2) 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
O1 H1B 0.8501 . ?
O1 H1A 0.8500 . ?
C1 N1 1.323(4) . ?
C1 C2 1.365(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.363(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.409(4) . ?
C3 H3 0.9300 . ?
C4 C12 1.416(4) . ?
C4 C5 1.438(4) . ?
C5 N3 1.386(3) . ?
C5 C6 1.388(3) . ?
C6 N4 1.371(3) . ?
C6 C7 1.431(3) . ?
C7 C8 1.399(4) . ?
C7 C11 1.402(4) . ?
C8 C9 1.375(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.397(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.323(4) . ?
C10 H10 0.9300 . ?
C11 N2 1.357(3) . ?
C11 C12 1.465(4) . ?
C12 N1 1.357(3) . ?
C13 N4 1.327(3) . ?
C13 N3 1.374(3) . ?
C13 C18 1.458(4) . ?
C14 N3 1.476(3) . ?
C14 C15 1.505(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.529(4) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.498(4) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.355(4) . ?
C18 S1 1.725(3) . ?
C19 C20 1.401(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.368(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.464(4) . ?
C21 S1 1.727(3) . ?
C22 C23 1.389(4) . ?
C22 C26 1.390(4) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9300 . ?
C24 N5 1.322(4) . ?
C24 H24 0.9300 . ?
C25 N5 1.335(4) . ?
C25 C26 1.376(4) . ?
C25 H25 0.9300 . ?
C26 H26 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
H1B O1 H1A 91.9 . . ?
N1 C1 C2 124.5(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 116.6(3) . . ?
C3 C4 C5 126.9(3) . . ?
C12 C4 C5 116.5(2) . . ?
N3 C5 C6 104.9(2) . . ?
N3 C5 C4 133.0(2) . . ?
C6 C5 C4 122.1(2) . . ?
N4 C6 C5 111.2(2) . . ?
N4 C6 C7 126.8(2) . . ?
C5 C6 C7 121.9(2) . . ?
C8 C7 C11 118.9(3) . . ?
C8 C7 C6 123.3(3) . . ?
C11 C7 C6 117.8(3) . . ?
C9 C8 C7 119.1(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C10 117.8(3) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 124.8(3) . . ?
N2 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
N2 C11 C7 121.9(3) . . ?
N2 C11 C12 117.7(2) . . ?
C7 C11 C12 120.4(2) . . ?
N1 C12 C4 122.4(3) . . ?
N1 C12 C11 116.4(3) . . ?
C4 C12 C11 121.2(2) . . ?
N4 C13 N3 112.1(2) . . ?
N4 C13 C18 120.7(2) . . ?
N3 C13 C18 127.2(2) . . ?
N3 C14 C15 112.4(2) . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14B 109.1 . . ?
C15 C14 H14B 109.1 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.7(3) . . ?
C14 C15 H15A 109.0 . . ?
C16 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
C16 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 114.8(3) . . ?
C17 C16 H16A 108.6 . . ?
C15 C16 H16A 108.6 . . ?
C17 C16 H16B 108.6 . . ?
C15 C16 H16B 108.6 . . ?
H16A C16 H16B 107.5 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C13 134.7(3) . . ?
C19 C18 S1 110.3(2) . . ?
C13 C18 S1 115.02(19) . . ?
C18 C19 C20 113.7(3) . . ?
C18 C19 H19 123.1 . . ?
C20 C19 H19 123.1 . . ?
C21 C20 C19 113.7(3) . . ?
C21 C20 H20 123.2 . . ?
C19 C20 H20 123.2 . . ?
C20 C21 C22 128.8(3) . . ?
C20 C21 S1 109.7(2) . . ?
C22 C21 S1 121.4(2) . . ?
C23 C22 C26 116.0(3) . . ?
C23 C22 C21 121.6(3) . . ?
C26 C22 C21 122.3(3) . . ?
C24 C23 C22 120.1(3) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
N5 C24 C23 124.5(3) . . ?
N5 C24 H24 117.7 . . ?
C23 C24 H24 117.7 . . ?
N5 C25 C26 125.1(3) . . ?
N5 C25 H25 117.4 . . ?
C26 C25 H25 117.4 . . ?
C25 C26 C22 119.1(3) . . ?
C25 C26 H26 120.4 . . ?
C22 C26 H26 120.4 . . ?
C1 N1 C12 117.5(3) . . ?
C10 N2 C11 117.5(3) . . ?
C13 N3 C5 106.8(2) . . ?
C13 N3 C14 126.0(2) . . ?
C5 N3 C14 127.1(2) . . ?
C13 N4 C6 105.0(2) . . ?
C24 N5 C25 115.1(3) . . ?
C18 S1 C21 92.58(13) . . ?

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
N1 C1 C2 C3 1.2(6) . . . . ?
C1 C2 C3 C4 0.3(5) . . . . ?
C2 C3 C4 C12 -2.3(4) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
C3 C4 C5 N3 -0.3(5) . . . . ?
C12 C4 C5 N3 -179.3(3) . . . . ?
C3 C4 C5 C6 177.5(3) . . . . ?
C12 C4 C5 C6 -1.5(4) . . . . ?
N3 C5 C6 N4 0.7(3) . . . . ?
C4 C5 C6 N4 -177.6(2) . . . . ?
N3 C5 C6 C7 177.2(2) . . . . ?
C4 C5 C6 C7 -1.1(4) . . . . ?
N4 C6 C7 C8 -0.4(5) . . . . ?
C5 C6 C7 C8 -176.4(3) . . . . ?
N4 C6 C7 C11 177.9(3) . . . . ?
C5 C6 C7 C11 1.9(4) . . . . ?
C11 C7 C8 C9 -1.9(4) . . . . ?
C6 C7 C8 C9 176.4(3) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C8 C9 C10 N2 -0.7(5) . . . . ?
C8 C7 C11 N2 1.2(4) . . . . ?
C6 C7 C11 N2 -177.2(3) . . . . ?
C8 C7 C11 C12 178.2(2) . . . . ?
C6 C7 C11 C12 -0.2(4) . . . . ?
C3 C4 C12 N1 3.2(4) . . . . ?
C5 C4 C12 N1 -177.7(3) . . . . ?
C3 C4 C12 C11 -175.8(3) . . . . ?
C5 C4 C12 C11 3.2(4) . . . . ?
N2 C11 C12 N1 -4.5(4) . . . . ?
C7 C11 C12 N1 178.4(3) . . . . ?
N2 C11 C12 C4 174.7(3) . . . . ?
C7 C11 C12 C4 -2.5(4) . . . . ?
N3 C14 C15 C16 170.6(2) . . . . ?
C14 C15 C16 C17 61.2(4) . . . . ?
N4 C13 C18 C19 -172.8(3) . . . . ?
N3 C13 C18 C19 6.9(5) . . . . ?
N4 C13 C18 S1 5.6(4) . . . . ?
N3 C13 C18 S1 -174.7(2) . . . . ?
C13 C18 C19 C20 179.0(3) . . . . ?
S1 C18 C19 C20 0.6(3) . . . . ?
C18 C19 C20 C21 -0.5(4) . . . . ?
C19 C20 C21 C22 -178.9(3) . . . . ?
C19 C20 C21 S1 0.1(3) . . . . ?
C20 C21 C22 C23 -4.5(5) . . . . ?
S1 C21 C22 C23 176.6(2) . . . . ?
C20 C21 C22 C26 175.7(3) . . . . ?
S1 C21 C22 C26 -3.2(4) . . . . ?
C26 C22 C23 C24 0.6(5) . . . . ?
C21 C22 C23 C24 -179.2(3) . . . . ?
C22 C23 C24 N5 0.1(6) . . . . ?
N5 C25 C26 C22 -0.4(6) . . . . ?
C23 C22 C26 C25 -0.5(5) . . . . ?
C21 C22 C26 C25 179.3(3) . . . . ?
C2 C1 N1 C12 -0.3(5) . . . . ?
C4 C12 N1 C1 -2.0(5) . . . . ?
C11 C12 N1 C1 177.2(3) . . . . ?
C9 C10 N2 C11 -0.1(5) . . . . ?
C7 C11 N2 C10 -0.2(4) . . . . ?
C12 C11 N2 C10 -177.3(3) . . . . ?
N4 C13 N3 C5 0.7(3) . . . . ?
C18 C13 N3 C5 -179.0(3) . . . . ?
N4 C13 N3 C14 -177.9(2) . . . . ?
C18 C13 N3 C14 2.4(4) . . . . ?
C6 C5 N3 C13 -0.8(3) . . . . ?
C4 C5 N3 C13 177.3(3) . . . . ?
C6 C5 N3 C14 177.7(2) . . . . ?
C4 C5 N3 C14 -4.2(5) . . . . ?
C15 C14 N3 C13 -92.7(3) . . . . ?
C15 C14 N3 C5 89.0(3) . . . . ?
N3 C13 N4 C6 -0.2(3) . . . . ?
C18 C13 N4 C6 179.5(2) . . . . ?
C5 C6 N4 C13 -0.3(3) . . . . ?
C7 C6 N4 C13 -176.6(3) . . . . ?
C23 C24 N5 C25 -0.9(6) . . . . ?
C26 C25 N5 C24 1.1(6) . . . . ?
C19 C18 S1 C21 -0.4(2) . . . . ?
C13 C18 S1 C21 -179.2(2) . . . . ?
C20 C21 S1 C18 0.2(2) . . . . ?
C22 C21 S1 C18 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.320
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_7
_database_code_depnum_ccdc_archive 'CCDC 1018238'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C64 H60 Cl6 N8 O5 S2'
_chemical_formula_sum            'C64 H60 Cl6 N8 O5 S2'
_chemical_formula_weight         1298.04

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   13.859(7)
_cell_length_b                   14.839(7)
_cell_length_c                   15.848(8)
_cell_angle_alpha                74.914(10)
_cell_angle_beta                 84.666(9)
_cell_angle_gamma                87.572(10)
_cell_volume                     3133(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    10947
_cell_measurement_theta_min      2.254
_cell_measurement_theta_max      19.336

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1348
_exptl_absorpt_coefficient_mu    0.397
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9613
_exptl_absorpt_correction_T_max  0.9613
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17735
_diffrn_reflns_av_R_equivalents  0.0834
_diffrn_reflns_av_sigmaI/netI    0.1003
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         25.00
_reflns_number_total             10947
_reflns_number_gt                4235
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0998P)²+0.0890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10947
_refine_ls_number_parameters     770
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0756
_refine_ls_wR_factor_ref         0.2283
_refine_ls_wR_factor_gt          0.2019
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_restrained_S_all      0.915
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.3067(4) 0.1264(4) 0.1750(4) 0.0976(18) Uani 1 1 d . . .
H1 H -0.3468 0.1288 0.1306 0.117 Uiso 1 1 calc R . .
C2 C -0.3485(4) 0.1072(4) 0.2611(4) 0.0959(17) Uani 1 1 d . . .
H2 H -0.4145 0.0962 0.2737 0.115 Uiso 1 1 calc R . .
C3 C -0.2901(4) 0.1050(4) 0.3261(3) 0.0881(16) Uani 1 1 d . . .
H3 H -0.3163 0.0928 0.3840 0.106 Uiso 1 1 calc R . .
C4 C -0.1913(4) 0.1209(3) 0.3063(3) 0.0707(13) Uani 1 1 d . . .
C5 C -0.1208(4) 0.1230(3) 0.3671(3) 0.0655(12) Uani 1 1 d . . .
C6 C -0.0243(4) 0.1372(3) 0.3410(3) 0.0668(12) Uani 1 1 d . . .
C7 C 0.0143(4) 0.1526(3) 0.2506(3) 0.0687(13) Uani 1 1 d . . .
C8 C 0.1118(4) 0.1648(4) 0.2225(3) 0.0880(16) Uani 1 1 d . . .
H8 H 0.1575 0.1639 0.2622 0.106 Uiso 1 1 calc R . .
C9 C 0.1390(4) 0.1780(4) 0.1351(4) 0.1051(19) Uani 1 1 d . . .
H9 H 0.2038 0.1870 0.1141 0.126 Uiso 1 1 calc R . .
C10 C 0.0693(5) 0.1780(4) 0.0784(3) 0.1011(19) Uani 1 1 d . . .
H10 H 0.0895 0.1854 0.0195 0.121 Uiso 1 1 calc R . .
C11 C -0.0528(4) 0.1537(3) 0.1889(3) 0.0725(13) Uani 1 1 d . . .
C12 C -0.1556(4) 0.1392(3) 0.2165(3) 0.0710(13) Uani 1 1 d . . .
C13 C -0.0364(4) 0.1198(3) 0.4796(3) 0.0653(12) Uani 1 1 d . . .
C14 C -0.2188(4) 0.1085(4) 0.5159(3) 0.0848(15) Uani 1 1 d . . .
H14A H -0.2698 0.1442 0.4833 0.102 Uiso 1 1 calc R . .
H14B H -0.2071 0.1374 0.5623 0.102 Uiso 1 1 calc R . .
C15 C -0.2516(4) 0.0110(4) 0.5557(4) 0.0993(18) Uani 1 1 d . . .
H15A H -0.1980 -0.0266 0.5822 0.119 Uiso 1 1 calc R . .
H15B H -0.2709 -0.0152 0.5100 0.119 Uiso 1 1 calc R . .
C16 C -0.3390(6) 0.0065(6) 0.6274(5) 0.156(3) Uani 1 1 d D . .
H16A H -0.3488 -0.0583 0.6588 0.187 Uiso 1 1 calc R . .
H16B H -0.3213 0.0391 0.6692 0.187 Uiso 1 1 calc R . .
C17 C -0.4265(7) 0.0442(9) 0.5962(7) 0.257(6) Uani 1 1 d D . .
H17A H -0.4192 0.1096 0.5685 0.385 Uiso 1 1 calc R . .
H17B H -0.4757 0.0362 0.6442 0.385 Uiso 1 1 calc R . .
H17C H -0.4450 0.0129 0.5544 0.385 Uiso 1 1 calc R . .
C18 C -0.0071(3) 0.1130(3) 0.5660(3) 0.0698(13) Uani 1 1 d . . .
C19 C -0.0524(4) 0.0887(4) 0.6484(3) 0.0809(15) Uani 1 1 d . . .
H19 H -0.1174 0.0729 0.6596 0.097 Uiso 1 1 calc R . .
C20 C 0.0063(4) 0.0895(4) 0.7141(3) 0.0821(15) Uani 1 1 d . . .
H20 H -0.0153 0.0748 0.7733 0.099 Uiso 1 1 calc R . .
C21 C 0.0999(4) 0.1145(3) 0.6828(3) 0.0677(13) Uani 1 1 d . . .
C22 C 0.1812(4) 0.1217(3) 0.7327(3) 0.0706(13) Uani 1 1 d . . .
C23 C 0.2722(4) 0.1503(4) 0.6922(3) 0.0838(15) Uani 1 1 d . . .
H23 H 0.2818 0.1658 0.6314 0.101 Uiso 1 1 calc R . .
C24 C 0.3482(4) 0.1561(4) 0.7403(3) 0.0912(16) Uani 1 1 d . . .
H24 H 0.4081 0.1761 0.7116 0.109 Uiso 1 1 calc R . .
C25 C 0.3367(4) 0.1328(4) 0.8304(3) 0.0784(14) Uani 1 1 d . . .
C26 C 0.2471(4) 0.1033(4) 0.8702(3) 0.0848(15) Uani 1 1 d . . .
H26 H 0.2382 0.0869 0.9311 0.102 Uiso 1 1 calc R . .
C27 C 0.1708(4) 0.0972(4) 0.8239(3) 0.0838(15) Uani 1 1 d . . .
H27 H 0.1114 0.0767 0.8533 0.101 Uiso 1 1 calc R . .
C28 C 0.4200(4) 0.1404(4) 0.8797(4) 0.0865(15) Uani 1 1 d . . .
C29 C 0.4726(4) 0.1167(5) 1.0237(4) 0.114(2) Uani 1 1 d . . .
H29A H 0.4985 0.1790 1.0109 0.137 Uiso 1 1 calc R . .
H29B H 0.5251 0.0737 1.0153 0.137 Uiso 1 1 calc R . .
C30 C 0.4278(5) 0.0890(6) 1.1147(4) 0.152(3) Uani 1 1 d . . .
H30A H 0.3757 0.1318 1.1220 0.228 Uiso 1 1 calc R . .
H30B H 0.4756 0.0902 1.1545 0.228 Uiso 1 1 calc R . .
H30C H 0.4031 0.0271 1.1267 0.228 Uiso 1 1 calc R . .
C31 C -0.2600(4) 0.3545(4) 0.2816(4) 0.0894(16) Uani 1 1 d . . .
H31 H -0.3034 0.3525 0.2408 0.107 Uiso 1 1 calc R . .
C32 C -0.1634(4) 0.3681(4) 0.2524(3) 0.0851(15) Uani 1 1 d . . .
H32 H -0.1424 0.3750 0.1936 0.102 Uiso 1 1 calc R . .
C33 C -0.0993(4) 0.3713(3) 0.3122(3) 0.0757(14) Uani 1 1 d . . .
H33 H -0.0340 0.3808 0.2940 0.091 Uiso 1 1 calc R . .
C34 C -0.1316(3) 0.3602(3) 0.4008(3) 0.0666(12) Uani 1 1 d . . .
C35 C -0.0738(3) 0.3626(3) 0.4708(3) 0.0665(12) Uani 1 1 d . . .
C36 C -0.1127(3) 0.3519(3) 0.5555(3) 0.0659(12) Uani 1 1 d . . .
C37 C -0.2134(3) 0.3355(3) 0.5799(3) 0.0706(13) Uani 1 1 d . . .
C38 C -0.2551(4) 0.3188(4) 0.6670(3) 0.0876(16) Uani 1 1 d . . .
H38 H -0.2172 0.3181 0.7126 0.105 Uiso 1 1 calc R . .
C39 C -0.3522(4) 0.3036(5) 0.6829(4) 0.1064(19) Uani 1 1 d . . .
H39 H -0.3814 0.2907 0.7399 0.128 Uiso 1 1 calc R . .
C40 C -0.4066(4) 0.3076(4) 0.6133(4) 0.1029(19) Uani 1 1 d . . .
H40 H -0.4732 0.3004 0.6250 0.123 Uiso 1 1 calc R . .
C41 C -0.2736(3) 0.3350(3) 0.5153(3) 0.0716(13) Uani 1 1 d . . .
C42 C -0.2322(4) 0.3471(3) 0.4235(3) 0.0705(13) Uani 1 1 d . . .
C43 C 0.0377(3) 0.3733(3) 0.5572(3) 0.0687(13) Uani 1 1 d . . .
C44 C 0.1022(4) 0.3631(6) 0.4066(4) 0.135(3) Uani 1 1 d U . .
H44A H 0.1580 0.3361 0.4376 0.162 Uiso 1 1 calc R . .
H44B H 0.0810 0.3174 0.3786 0.162 Uiso 1 1 calc R . .
C45 C 0.1328(5) 0.4390(6) 0.3422(4) 0.137(3) Uani 1 1 d U . .
H45A H 0.1646 0.4811 0.3680 0.164 Uiso 1 1 calc R . .
H45B H 0.0769 0.4718 0.3151 0.164 Uiso 1 1 calc R . .
C46 C 0.2050(5) 0.4120(5) 0.2694(4) 0.129(2) Uani 1 1 d U . .
H46A H 0.2552 0.3704 0.2974 0.155 Uiso 1 1 calc R . .
H46B H 0.1702 0.3787 0.2370 0.155 Uiso 1 1 calc R . .
C47 C 0.2506(6) 0.4948(6) 0.2076(5) 0.177(4) Uani 1 1 d U . .
H47A H 0.2013 0.5351 0.1781 0.265 Uiso 1 1 calc R . .
H47B H 0.2947 0.4751 0.1653 0.265 Uiso 1 1 calc R . .
H47C H 0.2853 0.5279 0.2394 0.265 Uiso 1 1 calc R . .
C48 C 0.1277(4) 0.3873(3) 0.5919(3) 0.0689(13) Uani 1 1 d . . .
C49 C 0.2176(4) 0.4138(3) 0.5537(3) 0.0763(14) Uani 1 1 d . . .
H49 H 0.2335 0.4271 0.4935 0.092 Uiso 1 1 calc R . .
C50 C 0.2832(4) 0.4189(4) 0.6128(3) 0.0803(14) Uani 1 1 d . . .
H50 H 0.3472 0.4364 0.5962 0.096 Uiso 1 1 calc R . .
C51 C 0.2443(3) 0.3958(3) 0.6986(3) 0.0731(13) Uani 1 1 d . . .
C52 C 0.2939(4) 0.3897(3) 0.7776(3) 0.0744(13) Uani 1 1 d . . .
C53 C 0.3909(4) 0.4116(4) 0.7716(3) 0.0942(17) Uani 1 1 d . . .
H53 H 0.4243 0.4316 0.7166 0.113 Uiso 1 1 calc R . .
C54 C 0.4386(4) 0.4044(4) 0.8448(3) 0.0909(16) Uani 1 1 d . . .
H54 H 0.5037 0.4199 0.8386 0.109 Uiso 1 1 calc R . .
C55 C 0.3922(5) 0.3745(4) 0.9277(3) 0.0886(16) Uani 1 1 d . . .
C56 C 0.2958(5) 0.3559(4) 0.9337(4) 0.1063(19) Uani 1 1 d . . .
H56 H 0.2624 0.3380 0.9889 0.128 Uiso 1 1 calc R . .
C57 C 0.2468(4) 0.3627(4) 0.8613(4) 0.0999(18) Uani 1 1 d . . .
H57 H 0.1812 0.3491 0.8682 0.120 Uiso 1 1 calc R . .
C58 C 0.4429(6) 0.3640(4) 1.0085(4) 0.106(2) Uani 1 1 d . . .
C59 C 0.5903(5) 0.3717(5) 1.0674(4) 0.121(2) Uani 1 1 d . . .
H59A H 0.5833 0.3089 1.1049 0.145 Uiso 1 1 calc R . .
H59B H 0.5674 0.4156 1.1011 0.145 Uiso 1 1 calc R . .
C60 C 0.6942(6) 0.3895(6) 1.0329(4) 0.149(3) Uani 1 1 d . . .
H60A H 0.7146 0.3481 0.9968 0.224 Uiso 1 1 calc R . .
H60B H 0.7340 0.3788 1.0811 0.224 Uiso 1 1 calc R . .
H60C H 0.7005 0.4530 0.9986 0.224 Uiso 1 1 calc R . .
C61 C 0.1550(4) 0.8386(5) 0.0551(3) 0.1034(19) Uani 1 1 d . . .
H61 H 0.1523 0.8293 -0.0037 0.124 Uiso 1 1 calc R . .
C62 C 0.4781(4) 0.3248(5) 0.3938(4) 0.116(2) Uani 1 1 d . . .
H62 H 0.5454 0.3148 0.4086 0.139 Uiso 1 1 calc R . .
C63 C -0.0190(8) 0.4061(7) 1.0077(9) 0.218(6) Uani 1 1 d D . .
H63A H -0.0108 0.3396 1.0132 0.262 Uiso 1 1 d R . .
H63B H -0.0846 0.4153 1.0316 0.262 Uiso 1 1 d R . .
C64 C 0.0082(9) 0.4633(9) 0.9208(7) 0.294(9) Uani 1 1 d D . .
H64A H -0.0397 0.5119 0.9048 0.441 Uiso 1 1 calc R . .
H64B H 0.0123 0.4255 0.8798 0.441 Uiso 1 1 calc R . .
H64C H 0.0700 0.4905 0.9201 0.441 Uiso 1 1 calc R . .
Cl1 Cl 0.08361(14) 0.75411(13) 0.12958(12) 0.1342(7) Uani 1 1 d . . .
Cl2 Cl 0.10704(16) 0.94830(14) 0.05516(11) 0.1470(8) Uani 1 1 d . . .
Cl3 Cl 0.27469(14) 0.82617(19) 0.08050(12) 0.1681(10) Uani 1 1 d . . .
Cl4 Cl 0.46972(13) 0.31558(18) 0.28807(12) 0.1562(9) Uani 1 1 d . . .
Cl5 Cl 0.40346(17) 0.24401(18) 0.46919(14) 0.1723(9) Uani 1 1 d . . .
Cl6 Cl 0.43563(13) 0.43802(16) 0.40233(12) 0.1435(7) Uani 1 1 d . . .
N1 N -0.2144(3) 0.1411(3) 0.1533(3) 0.0864(13) Uani 1 1 d . . .
N2 N -0.0246(4) 0.1681(3) 0.1024(2) 0.0910(13) Uani 1 1 d . . .
N3 N -0.1290(3) 0.1118(3) 0.4564(2) 0.0659(10) Uani 1 1 d . . .
N4 N 0.0288(3) 0.1342(3) 0.4105(2) 0.0687(10) Uani 1 1 d . . .
N5 N -0.2946(3) 0.3439(3) 0.3651(3) 0.0791(12) Uani 1 1 d . . .
N6 N -0.3701(3) 0.3210(3) 0.5310(3) 0.0867(12) Uani 1 1 d . . .
N7 N 0.0237(3) 0.3760(3) 0.4727(2) 0.0718(10) Uani 1 1 d U . .
N8 N -0.0436(3) 0.3586(3) 0.6092(2) 0.0717(11) Uani 1 1 d . . .
O1 O 0.4993(3) 0.1642(3) 0.8478(3) 0.1237(15) Uani 1 1 d . . .
O2 O 0.3974(2) 0.1146(3) 0.9666(3) 0.0953(11) Uani 1 1 d . . .
O3 O 0.4019(4) 0.3401(4) 1.0818(3) 0.1476(19) Uani 1 1 d . . .
O4 O 0.5361(4) 0.3839(3) 0.9913(2) 0.1099(13) Uani 1 1 d . . .
O5 O 0.0553(6) 0.4308(9) 1.0704(6) 0.286(5) Uani 1 1 d D . .
H5A H 0.0409 0.3977 1.1222 0.429 Uiso 1 1 d R . .
S1 S 0.11200(9) 0.13735(9) 0.57107(7) 0.0750(4) Uani 1 1 d . . .
S2 S 0.12482(9) 0.36701(10) 0.70425(8) 0.0808(4) 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
C1 N1 1.307(6) . ?
C1 C2 1.393(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.393(7) . ?
C3 H3 0.9300 . ?
C4 C12 1.422(6) . ?
C4 C5 1.441(6) . ?
C5 C6 1.371(6) . ?
C5 N3 1.376(5) . ?
C6 N4 1.372(5) . ?
C6 C7 1.445(6) . ?
C7 C8 1.387(6) . ?
C7 C11 1.407(6) . ?
C8 C9 1.366(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(8) . ?
C9 H9 0.9300 . ?
C10 N2 1.324(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.354(5) . ?
C11 C12 1.460(6) . ?
C12 N1 1.342(6) . ?
C13 N4 1.330(5) . ?
C13 N3 1.386(6) . ?
C13 C18 1.442(6) . ?
C14 N3 1.484(6) . ?
C14 C15 1.491(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.572(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.393(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.361(6) . ?
C18 S1 1.718(5) . ?
C19 C20 1.382(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.376(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.458(7) . ?
C21 S1 1.708(4) . ?
C22 C27 1.390(6) . ?
C22 C23 1.390(7) . ?
C23 C24 1.375(7) . ?
C23 H23 0.9300 . ?
C24 C25 1.374(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.375(7) . ?
C25 C28 1.477(7) . ?
C26 C27 1.361(7) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 O1 1.193(6) . ?
C28 O2 1.341(6) . ?
C29 O2 1.448(6) . ?
C29 C30 1.476(8) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C31 N5 1.336(6) . ?
C31 C32 1.381(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.368(7) . ?
C32 H32 0.9300 . ?
C33 C34 1.403(6) . ?
C33 H33 0.9300 . ?
C34 C42 1.416(6) . ?
C34 C35 1.436(6) . ?
C35 C36 1.371(6) . ?
C35 N7 1.378(6) . ?
C36 N8 1.361(6) . ?
C36 C37 1.427(6) . ?
C37 C41 1.381(6) . ?
C37 C38 1.408(6) . ?
C38 C39 1.363(7) . ?
C38 H38 0.9300 . ?
C39 C40 1.381(7) . ?
C39 H39 0.9300 . ?
C40 N6 1.322(6) . ?
C40 H40 0.9300 . ?
C41 N6 1.352(6) . ?
C41 C42 1.482(6) . ?
C42 N5 1.336(6) . ?
C43 N8 1.322(5) . ?
C43 N7 1.361(5) . ?
C43 C48 1.453(7) . ?
C44 C45 1.361(9) . ?
C44 N7 1.481(6) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C45 C46 1.575(8) . ?
C45 H45A 0.9700 . ?
C45 H45B 0.9700 . ?
C46 C47 1.480(9) . ?
C46 H46A 0.9700 . ?
C46 H46B 0.9700 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C48 C49 1.361(6) . ?
C48 S2 1.723(5) . ?
C49 C50 1.381(6) . ?
C49 H49 0.9300 . ?
C50 C51 1.376(6) . ?
C50 H50 0.9300 . ?
C51 C52 1.464(6) . ?
C51 S2 1.716(5) . ?
C52 C53 1.385(7) . ?
C52 C57 1.391(7) . ?
C53 C54 1.366(7) . ?
C53 H53 0.9300 . ?
C54 C55 1.378(7) . ?
C54 H54 0.9300 . ?
C55 C56 1.365(8) . ?
C55 C58 1.487(8) . ?
C56 C57 1.366(7) . ?
C56 H56 0.9300 . ?
C57 H57 0.9300 . ?
C58 O3 1.215(7) . ?
C58 O4 1.325(8) . ?
C59 O4 1.448(6) . ?
C59 C60 1.501(8) . ?
C59 H59A 0.9700 . ?
C59 H59B 0.9700 . ?
C60 H60A 0.9600 . ?
C60 H60B 0.9600 . ?
C60 H60C 0.9600 . ?
C61 Cl2 1.733(6) . ?
C61 Cl3 1.735(6) . ?
C61 Cl1 1.749(6) . ?
C61 H61 0.9800 . ?
C62 Cl4 1.731(6) . ?
C62 Cl5 1.751(6) . ?
C62 Cl6 1.790(7) . ?
C62 H62 0.9800 . ?
C63 C64 1.442(8) . ?
C63 O5 1.611(8) . ?
C63 H63A 0.9700 . ?
C63 H63B 0.9700 . ?
C64 O5 1.799(13) 2_567 ?
C64 H64A 0.9600 . ?
C64 H64B 0.9600 . ?
C64 H64C 0.9600 . ?
O5 C64 1.799(13) 2_567 ?
O5 H5A 0.8499 . ?

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
N1 C1 C2 123.7(5) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 120.3(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C12 117.1(4) . . ?
C3 C4 C5 126.9(4) . . ?
C12 C4 C5 116.0(5) . . ?
C6 C5 N3 105.6(4) . . ?
C6 C5 C4 122.3(4) . . ?
N3 C5 C4 132.1(5) . . ?
C5 C6 N4 111.7(4) . . ?
C5 C6 C7 122.8(4) . . ?
N4 C6 C7 125.5(5) . . ?
C8 C7 C11 119.4(4) . . ?
C8 C7 C6 124.0(4) . . ?
C11 C7 C6 116.6(5) . . ?
C9 C8 C7 118.3(5) . . ?
C9 C8 H8 120.9 . . ?
C7 C8 H8 120.9 . . ?
C8 C9 C10 119.2(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 124.4(5) . . ?
N2 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N2 C11 C7 121.5(5) . . ?
N2 C11 C12 117.8(4) . . ?
C7 C11 C12 120.7(4) . . ?
N1 C12 C4 121.7(5) . . ?
N1 C12 C11 116.7(4) . . ?
C4 C12 C11 121.6(4) . . ?
N4 C13 N3 111.9(4) . . ?
N4 C13 C18 120.5(4) . . ?
N3 C13 C18 127.6(4) . . ?
N3 C14 C15 112.1(4) . . ?
N3 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N3 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 112.1(5) . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C17 C16 C15 115.6(8) . . ?
C17 C16 H16A 108.4 . . ?
C15 C16 H16A 108.4 . . ?
C17 C16 H16B 108.4 . . ?
C15 C16 H16B 108.4 . . ?
H16A C16 H16B 107.4 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C13 134.4(5) . . ?
C19 C18 S1 109.6(4) . . ?
C13 C18 S1 115.9(3) . . ?
C18 C19 C20 114.4(5) . . ?
C18 C19 H19 122.8 . . ?
C20 C19 H19 122.8 . . ?
C21 C20 C19 113.1(4) . . ?
C21 C20 H20 123.5 . . ?
C19 C20 H20 123.5 . . ?
C20 C21 C22 128.2(4) . . ?
C20 C21 S1 110.0(4) . . ?
C22 C21 S1 121.8(4) . . ?
C27 C22 C23 117.3(5) . . ?
C27 C22 C21 120.5(5) . . ?
C23 C22 C21 122.2(4) . . ?
C24 C23 C22 121.4(5) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C23 120.7(5) . . ?
C25 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
C24 C25 C26 117.7(5) . . ?
C24 C25 C28 119.1(5) . . ?
C26 C25 C28 123.2(5) . . ?
C27 C26 C25 122.5(5) . . ?
C27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 C27 C22 120.3(5) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
O1 C28 O2 122.8(5) . . ?
O1 C28 C25 125.3(6) . . ?
O2 C28 C25 111.9(5) . . ?
O2 C29 C30 107.1(5) . . ?
O2 C29 H29A 110.3 . . ?
C30 C29 H29A 110.3 . . ?
O2 C29 H29B 110.3 . . ?
C30 C29 H29B 110.3 . . ?
H29A C29 H29B 108.5 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
N5 C31 C32 123.8(5) . . ?
N5 C31 H31 118.1 . . ?
C32 C31 H31 118.1 . . ?
C33 C32 C31 118.2(5) . . ?
C33 C32 H32 120.9 . . ?
C31 C32 H32 120.9 . . ?
C32 C33 C34 120.4(5) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C33 C34 C42 116.6(4) . . ?
C33 C34 C35 127.0(5) . . ?
C42 C34 C35 116.4(4) . . ?
C36 C35 N7 105.3(4) . . ?
C36 C35 C34 122.4(5) . . ?
N7 C35 C34 132.3(4) . . ?
N8 C36 C35 111.2(4) . . ?
N8 C36 C37 127.0(4) . . ?
C35 C36 C37 121.8(5) . . ?
C41 C37 C38 117.9(5) . . ?
C41 C37 C36 118.6(4) . . ?
C38 C37 C36 123.5(5) . . ?
C39 C38 C37 118.6(5) . . ?
C39 C38 H38 120.7 . . ?
C37 C38 H38 120.7 . . ?
C38 C39 C40 119.0(5) . . ?
C38 C39 H39 120.5 . . ?
C40 C39 H39 120.5 . . ?
N6 C40 C39 124.3(5) . . ?
N6 C40 H40 117.9 . . ?
C39 C40 H40 117.9 . . ?
N6 C41 C37 123.6(4) . . ?
N6 C41 C42 116.5(5) . . ?
C37 C41 C42 119.8(4) . . ?
N5 C42 C34 122.9(4) . . ?
N5 C42 C41 116.3(5) . . ?
C34 C42 C41 120.8(4) . . ?
N8 C43 N7 112.3(4) . . ?
N8 C43 C48 120.3(4) . . ?
N7 C43 C48 127.4(4) . . ?
C45 C44 N7 118.5(7) . . ?
C45 C44 H44A 107.7 . . ?
N7 C44 H44A 107.7 . . ?
C45 C44 H44B 107.7 . . ?
N7 C44 H44B 107.7 . . ?
H44A C44 H44B 107.1 . . ?
C44 C45 C46 112.4(7) . . ?
C44 C45 H45A 109.1 . . ?
C46 C45 H45A 109.1 . . ?
C44 C45 H45B 109.1 . . ?
C46 C45 H45B 109.1 . . ?
H45A C45 H45B 107.8 . . ?
C47 C46 C45 112.3(6) . . ?
C47 C46 H46A 109.1 . . ?
C45 C46 H46A 109.1 . . ?
C47 C46 H46B 109.1 . . ?
C45 C46 H46B 109.1 . . ?
H46A C46 H46B 107.9 . . ?
C46 C47 H47A 109.5 . . ?
C46 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C46 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C49 C48 C43 133.1(4) . . ?
C49 C48 S2 110.6(4) . . ?
C43 C48 S2 116.3(4) . . ?
C48 C49 C50 113.7(4) . . ?
C48 C49 H49 123.2 . . ?
C50 C49 H49 123.2 . . ?
C51 C50 C49 113.4(5) . . ?
C51 C50 H50 123.3 . . ?
C49 C50 H50 123.3 . . ?
C50 C51 C52 127.8(5) . . ?
C50 C51 S2 110.3(4) . . ?
C52 C51 S2 121.8(4) . . ?
C53 C52 C57 116.9(5) . . ?
C53 C52 C51 120.8(4) . . ?
C57 C52 C51 122.2(5) . . ?
C54 C53 C52 121.4(5) . . ?
C54 C53 H53 119.3 . . ?
C52 C53 H53 119.3 . . ?
C53 C54 C55 121.3(5) . . ?
C53 C54 H54 119.3 . . ?
C55 C54 H54 119.3 . . ?
C56 C55 C54 117.3(5) . . ?
C56 C55 C58 120.2(6) . . ?
C54 C55 C58 122.4(6) . . ?
C55 C56 C57 122.3(5) . . ?
C55 C56 H56 118.9 . . ?
C57 C56 H56 118.9 . . ?
C56 C57 C52 120.7(5) . . ?
C56 C57 H57 119.7 . . ?
C52 C57 H57 119.7 . . ?
O3 C58 O4 124.6(6) . . ?
O3 C58 C55 122.8(8) . . ?
O4 C58 C55 112.6(6) . . ?
O4 C59 C60 106.1(5) . . ?
O4 C59 H59A 110.5 . . ?
C60 C59 H59A 110.5 . . ?
O4 C59 H59B 110.5 . . ?
C60 C59 H59B 110.5 . . ?
H59A C59 H59B 108.7 . . ?
C59 C60 H60A 109.5 . . ?
C59 C60 H60B 109.5 . . ?
H60A C60 H60B 109.5 . . ?
C59 C60 H60C 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
Cl2 C61 Cl3 112.2(4) . . ?
Cl2 C61 Cl1 109.0(3) . . ?
Cl3 C61 Cl1 110.4(3) . . ?
Cl2 C61 H61 108.4 . . ?
Cl3 C61 H61 108.4 . . ?
Cl1 C61 H61 108.4 . . ?
Cl4 C62 Cl5 110.8(4) . . ?
Cl4 C62 Cl6 109.7(3) . . ?
Cl5 C62 Cl6 106.4(3) . . ?
Cl4 C62 H62 110.0 . . ?
Cl5 C62 H62 110.0 . . ?
Cl6 C62 H62 110.0 . . ?
C64 C63 O5 105.9(7) . . ?
C64 C63 H63A 113.8 . . ?
O5 C63 H63A 105.8 . . ?
C64 C63 H63B 116.1 . . ?
O5 C63 H63B 108.3 . . ?
H63A C63 H63B 106.3 . . ?
C63 C64 O5 98.7(9) . 2_567 ?
C63 C64 H64A 109.5 . . ?
O5 C64 H64A 26.4 2_567 . ?
C63 C64 H64B 109.5 . . ?
O5 C64 H64B 135.4 2_567 . ?
H64A C64 H64B 109.5 . . ?
C63 C64 H64C 109.5 . . ?
O5 C64 H64C 91.9 2_567 . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?
C1 N1 C12 118.9(4) . . ?
C10 N2 C11 117.3(4) . . ?
C5 N3 C13 106.4(4) . . ?
C5 N3 C14 128.2(4) . . ?
C13 N3 C14 124.7(4) . . ?
C13 N4 C6 104.4(4) . . ?
C42 N5 C31 118.0(4) . . ?
C40 N6 C41 116.6(5) . . ?
C43 N7 C35 106.4(4) . . ?
C43 N7 C44 124.0(4) . . ?
C35 N7 C44 126.5(4) . . ?
C43 N8 C36 104.7(4) . . ?
C28 O2 C29 118.2(5) . . ?
C58 O4 C59 115.2(5) . . ?
C63 O5 C64 94.3(7) . 2_567 ?
C63 O5 H5A 107.8 . . ?
C64 O5 H5A 98.6 2_567 . ?
C21 S1 C18 92.9(2) . . ?
C51 S2 C48 92.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 1.0(9) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C3 C4 C12 0.0(8) . . . . ?
C2 C3 C4 C5 178.6(5) . . . . ?
C3 C4 C5 C6 178.4(5) . . . . ?
C12 C4 C5 C6 -3.0(7) . . . . ?
C3 C4 C5 N3 -0.9(9) . . . . ?
C12 C4 C5 N3 177.7(5) . . . . ?
N3 C5 C6 N4 0.8(5) . . . . ?
C4 C5 C6 N4 -178.7(4) . . . . ?
N3 C5 C6 C7 -179.6(4) . . . . ?
C4 C5 C6 C7 0.9(7) . . . . ?
C5 C6 C7 C8 -178.2(5) . . . . ?
N4 C6 C7 C8 1.3(8) . . . . ?
C5 C6 C7 C11 0.8(7) . . . . ?
N4 C6 C7 C11 -179.6(4) . . . . ?
C11 C7 C8 C9 0.5(8) . . . . ?
C6 C7 C8 C9 179.4(5) . . . . ?
C7 C8 C9 C10 -0.6(9) . . . . ?
C8 C9 C10 N2 1.7(10) . . . . ?
C8 C7 C11 N2 -1.4(7) . . . . ?
C6 C7 C11 N2 179.6(4) . . . . ?
C8 C7 C11 C12 178.7(5) . . . . ?
C6 C7 C11 C12 -0.3(7) . . . . ?
C3 C4 C12 N1 0.0(7) . . . . ?
C5 C4 C12 N1 -178.7(4) . . . . ?
C3 C4 C12 C11 -177.9(5) . . . . ?
C5 C4 C12 C11 3.4(7) . . . . ?
N2 C11 C12 N1 0.2(7) . . . . ?
C7 C11 C12 N1 -179.9(4) . . . . ?
N2 C11 C12 C4 178.2(5) . . . . ?
C7 C11 C12 C4 -1.8(7) . . . . ?
N3 C14 C15 C16 173.0(5) . . . . ?
C14 C15 C16 C17 69.2(10) . . . . ?
N4 C13 C18 C19 -171.0(5) . . . . ?
N3 C13 C18 C19 8.0(9) . . . . ?
N4 C13 C18 S1 6.9(6) . . . . ?
N3 C13 C18 S1 -174.0(4) . . . . ?
C13 C18 C19 C20 178.2(5) . . . . ?
S1 C18 C19 C20 0.1(6) . . . . ?
C18 C19 C20 C21 -0.4(7) . . . . ?
C19 C20 C21 C22 -179.2(5) . . . . ?
C19 C20 C21 S1 0.5(6) . . . . ?
C20 C21 C22 C27 3.6(8) . . . . ?
S1 C21 C22 C27 -176.1(4) . . . . ?
C20 C21 C22 C23 -178.2(5) . . . . ?
S1 C21 C22 C23 2.0(7) . . . . ?
C27 C22 C23 C24 -1.4(8) . . . . ?
C21 C22 C23 C24 -179.6(5) . . . . ?
C22 C23 C24 C25 0.7(9) . . . . ?
C23 C24 C25 C26 0.2(8) . . . . ?
C23 C24 C25 C28 -179.7(5) . . . . ?
C24 C25 C26 C27 -0.4(8) . . . . ?
C28 C25 C26 C27 179.5(5) . . . . ?
C25 C26 C27 C22 -0.3(9) . . . . ?
C23 C22 C27 C26 1.2(8) . . . . ?
C21 C22 C27 C26 179.4(5) . . . . ?
C24 C25 C28 O1 -1.4(9) . . . . ?
C26 C25 C28 O1 178.7(6) . . . . ?
C24 C25 C28 O2 -179.5(5) . . . . ?
C26 C25 C28 O2 0.6(8) . . . . ?
N5 C31 C32 C33 -0.2(9) . . . . ?
C31 C32 C33 C34 0.4(8) . . . . ?
C32 C33 C34 C42 -0.8(7) . . . . ?
C32 C33 C34 C35 -179.4(5) . . . . ?
C33 C34 C35 C36 179.3(5) . . . . ?
C42 C34 C35 C36 0.6(7) . . . . ?
C33 C34 C35 N7 0.4(8) . . . . ?
C42 C34 C35 N7 -178.2(5) . . . . ?
N7 C35 C36 N8 0.3(5) . . . . ?
C34 C35 C36 N8 -178.8(4) . . . . ?
N7 C35 C36 C37 -179.4(4) . . . . ?
C34 C35 C36 C37 1.5(7) . . . . ?
N8 C36 C37 C41 177.2(5) . . . . ?
C35 C36 C37 C41 -3.2(7) . . . . ?
N8 C36 C37 C38 -3.5(8) . . . . ?
C35 C36 C37 C38 176.1(5) . . . . ?
C41 C37 C38 C39 -0.4(8) . . . . ?
C36 C37 C38 C39 -179.8(5) . . . . ?
C37 C38 C39 C40 -1.7(9) . . . . ?
C38 C39 C40 N6 3.4(10) . . . . ?
C38 C37 C41 N6 1.2(8) . . . . ?
C36 C37 C41 N6 -179.4(5) . . . . ?
C38 C37 C41 C42 -176.7(5) . . . . ?
C36 C37 C41 C42 2.7(7) . . . . ?
C33 C34 C42 N5 0.9(7) . . . . ?
C35 C34 C42 N5 179.7(4) . . . . ?
C33 C34 C42 C41 -179.8(4) . . . . ?
C35 C34 C42 C41 -1.0(7) . . . . ?
N6 C41 C42 N5 0.6(7) . . . . ?
C37 C41 C42 N5 178.6(4) . . . . ?
N6 C41 C42 C34 -178.6(4) . . . . ?
C37 C41 C42 C34 -0.7(7) . . . . ?
N7 C44 C45 C46 -171.5(5) . . . . ?
C44 C45 C46 C47 -170.5(7) . . . . ?
N8 C43 C48 C49 -171.2(5) . . . . ?
N7 C43 C48 C49 6.6(9) . . . . ?
N8 C43 C48 S2 8.9(6) . . . . ?
N7 C43 C48 S2 -173.2(4) . . . . ?
C43 C48 C49 C50 179.5(5) . . . . ?
S2 C48 C49 C50 -0.7(6) . . . . ?
C48 C49 C50 C51 0.3(7) . . . . ?
C49 C50 C51 C52 177.0(5) . . . . ?
C49 C50 C51 S2 0.2(6) . . . . ?
C50 C51 C52 C53 2.4(8) . . . . ?
S2 C51 C52 C53 178.8(4) . . . . ?
C50 C51 C52 C57 -178.1(5) . . . . ?
S2 C51 C52 C57 -1.7(7) . . . . ?
C57 C52 C53 C54 1.8(9) . . . . ?
C51 C52 C53 C54 -178.6(5) . . . . ?
C52 C53 C54 C55 0.3(9) . . . . ?
C53 C54 C55 C56 -2.5(9) . . . . ?
C53 C54 C55 C58 178.7(6) . . . . ?
C54 C55 C56 C57 2.5(9) . . . . ?
C58 C55 C56 C57 -178.6(6) . . . . ?
C55 C56 C57 C52 -0.4(10) . . . . ?
C53 C52 C57 C56 -1.8(9) . . . . ?
C51 C52 C57 C56 178.6(5) . . . . ?
C56 C55 C58 O3 -0.8(10) . . . . ?
C54 C55 C58 O3 178.0(6) . . . . ?
C56 C55 C58 O4 179.4(6) . . . . ?
C54 C55 C58 O4 -1.8(9) . . . . ?
O5 C63 C64 O5 -83.0(8) . . . 2_567 ?
C2 C1 N1 C12 -1.0(9) . . . . ?
C4 C12 N1 C1 0.4(8) . . . . ?
C11 C12 N1 C1 178.5(5) . . . . ?
C9 C10 N2 C11 -2.6(9) . . . . ?
C7 C11 N2 C10 2.3(8) . . . . ?
C12 C11 N2 C10 -177.8(5) . . . . ?
C6 C5 N3 C13 -0.1(5) . . . . ?
C4 C5 N3 C13 179.3(5) . . . . ?
C6 C5 N3 C14 170.0(4) . . . . ?
C4 C5 N3 C14 -10.6(8) . . . . ?
N4 C13 N3 C5 -0.7(5) . . . . ?
C18 C13 N3 C5 -179.8(4) . . . . ?
N4 C13 N3 C14 -171.2(4) . . . . ?
C18 C13 N3 C14 9.7(7) . . . . ?
C15 C14 N3 C5 93.5(6) . . . . ?
C15 C14 N3 C13 -98.1(6) . . . . ?
N3 C13 N4 C6 1.1(5) . . . . ?
C18 C13 N4 C6 -179.7(4) . . . . ?
C5 C6 N4 C13 -1.2(5) . . . . ?
C7 C6 N4 C13 179.2(4) . . . . ?
C34 C42 N5 C31 -0.7(7) . . . . ?
C41 C42 N5 C31 -180.0(4) . . . . ?
C32 C31 N5 C42 0.3(8) . . . . ?
C39 C40 N6 C41 -2.6(9) . . . . ?
C37 C41 N6 C40 0.3(8) . . . . ?
C42 C41 N6 C40 178.2(5) . . . . ?
N8 C43 N7 C35 0.4(5) . . . . ?
C48 C43 N7 C35 -177.6(5) . . . . ?
N8 C43 N7 C44 -161.0(5) . . . . ?
C48 C43 N7 C44 21.0(8) . . . . ?
C36 C35 N7 C43 -0.4(5) . . . . ?
C34 C35 N7 C43 178.6(5) . . . . ?
C36 C35 N7 C44 160.4(5) . . . . ?
C34 C35 N7 C44 -20.6(9) . . . . ?
C45 C44 N7 C43 -106.8(7) . . . . ?
C45 C44 N7 C35 95.6(7) . . . . ?
N7 C43 N8 C36 -0.2(5) . . . . ?
C48 C43 N8 C36 177.9(4) . . . . ?
C35 C36 N8 C43 -0.1(5) . . . . ?
C37 C36 N8 C43 179.6(5) . . . . ?
O1 C28 O2 C29 0.7(8) . . . . ?
C25 C28 O2 C29 178.8(5) . . . . ?
C30 C29 O2 C28 177.8(5) . . . . ?
O3 C58 O4 C59 2.3(10) . . . . ?
C55 C58 O4 C59 -177.9(5) . . . . ?
C60 C59 O4 C58 175.1(6) . . . . ?
C64 C63 O5 C64 79.7(10) . . . 2_567 ?
C20 C21 S1 C18 -0.4(4) . . . . ?
C22 C21 S1 C18 179.4(4) . . . . ?
C19 C18 S1 C21 0.2(4) . . . . ?
C13 C18 S1 C21 -178.3(4) . . . . ?
C50 C51 S2 C48 -0.5(4) . . . . ?
C52 C51 S2 C48 -177.5(4) . . . . ?
C49 C48 S2 C51 0.7(4) . . . . ?
C43 C48 S2 C51 -179.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.649
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_8
_database_code_depnum_ccdc_archive 'CCDC 1018239'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H32 Cl3 N5 S'
_chemical_formula_sum            'C40 H32 Cl3 N5 S'
_chemical_formula_weight         721.12

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   21.9934(17)
_cell_length_b                   9.0584(7)
_cell_length_c                   19.5200(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.8150(10)
_cell_angle_gamma                90.00
_cell_volume                     3584.6(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    6317
_cell_measurement_theta_min      2.257
_cell_measurement_theta_max      18.507

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1496
_exptl_absorpt_coefficient_mu    0.351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9658
_exptl_absorpt_correction_T_max  0.9658
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            19443
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_sigmaI/netI    0.0634
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6317
_reflns_number_gt                3364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0851P)²+1.8680P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6317
_refine_ls_number_parameters     442
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1288
_refine_ls_R_factor_gt           0.0706
_refine_ls_wR_factor_ref         0.1989
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.018
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7966(2) 0.3741(6) 0.7177(3) 0.0838(16) Uani 1 1 d . . .
H1 H 0.8363 0.3266 0.7442 0.101 Uiso 1 1 calc R . .
C2 C 0.7915(2) 0.4530(6) 0.6550(3) 0.0773(14) Uani 1 1 d . . .
H2 H 0.8270 0.4590 0.6404 0.093 Uiso 1 1 calc R . .
C3 C 0.7337(2) 0.5215(5) 0.6155(2) 0.0660(12) Uani 1 1 d . . .
H3 H 0.7287 0.5731 0.5724 0.079 Uiso 1 1 calc R . .
C4 C 0.6811(2) 0.5148(5) 0.6394(2) 0.0558(10) Uani 1 1 d . . .
C5 C 0.61778(19) 0.5838(5) 0.6046(2) 0.0529(10) Uani 1 1 d . . .
C6 C 0.56890(19) 0.5690(5) 0.6319(2) 0.0519(10) Uani 1 1 d . . .
C7 C 0.57835(19) 0.4850(5) 0.6972(2) 0.0561(11) Uani 1 1 d . . .
C8 C 0.5298(2) 0.4677(6) 0.7268(2) 0.0705(13) Uani 1 1 d . . .
H8 H 0.4892 0.5143 0.7048 0.085 Uiso 1 1 calc R . .
C9 C 0.5434(3) 0.3812(6) 0.7885(3) 0.0810(15) Uani 1 1 d . . .
H9 H 0.5123 0.3677 0.8093 0.097 Uiso 1 1 calc R . .
C10 C 0.6048(3) 0.3145(6) 0.8191(3) 0.0845(15) Uani 1 1 d . . .
H10 H 0.6134 0.2554 0.8608 0.101 Uiso 1 1 calc R . .
C11 C 0.6391(2) 0.4138(5) 0.7328(2) 0.0585(11) Uani 1 1 d . . .
C12 C 0.6915(2) 0.4300(5) 0.7042(2) 0.0578(11) Uani 1 1 d . . .
C13 C 0.52666(18) 0.7007(5) 0.5338(2) 0.0533(10) Uani 1 1 d . . .
C14 C 0.6259(2) 0.7494(6) 0.4998(3) 0.0769(14) Uani 1 1 d DU . .
H14A H 0.6048 0.8439 0.4822 0.092 Uiso 1 1 calc R . .
H14B H 0.6710 0.7683 0.5336 0.092 Uiso 1 1 calc R . .
C15 C 0.6263(3) 0.6648(7) 0.4374(3) 0.0976(18) Uani 1 1 d DU . .
H15A H 0.5813 0.6441 0.4037 0.117 Uiso 1 1 calc R . .
H15B H 0.6485 0.5714 0.4547 0.117 Uiso 1 1 calc R . .
C16 C 0.6625(4) 0.7528(8) 0.3957(4) 0.132(3) Uani 1 1 d DU . .
H16A H 0.6412 0.8483 0.3820 0.158 Uiso 1 1 calc R . .
H16B H 0.7074 0.7705 0.4302 0.158 Uiso 1 1 calc R . .
C17 C 0.6649(5) 0.6859(11) 0.3294(4) 0.190(4) Uani 1 1 d DU . .
H17A H 0.6898 0.5959 0.3425 0.286 Uiso 1 1 calc R . .
H17B H 0.6857 0.7526 0.3070 0.286 Uiso 1 1 calc R . .
H17C H 0.6209 0.6648 0.2949 0.286 Uiso 1 1 calc R . .
C18 C 0.47818(19) 0.7861(5) 0.4750(2) 0.0538(10) Uani 1 1 d . . .
C19 C 0.4751(2) 0.8499(5) 0.4109(2) 0.0702(13) Uani 1 1 d . . .
H19 H 0.5099 0.8475 0.3951 0.084 Uiso 1 1 calc R . .
C20 C 0.4150(2) 0.9197(5) 0.3706(2) 0.0661(12) Uani 1 1 d . . .
H20 H 0.4064 0.9683 0.3258 0.079 Uiso 1 1 calc R . .
C21 C 0.37026(18) 0.9101(5) 0.4028(2) 0.0529(10) Uani 1 1 d . . .
C22 C 0.30307(18) 0.9676(5) 0.3796(2) 0.0529(10) Uani 1 1 d . . .
C23 C 0.2757(2) 1.0639(5) 0.3194(2) 0.0656(12) Uani 1 1 d . . .
H23 H 0.2999 1.0883 0.2912 0.079 Uiso 1 1 calc R . .
C24 C 0.2141(2) 1.1230(5) 0.3010(2) 0.0677(13) Uani 1 1 d . . .
H24 H 0.1973 1.1870 0.2607 0.081 Uiso 1 1 calc R . .
C25 C 0.17632(19) 1.0888(5) 0.3418(2) 0.0559(11) Uani 1 1 d . . .
C26 C 0.2024(2) 0.9910(5) 0.3997(2) 0.0638(12) Uani 1 1 d . . .
H26 H 0.1776 0.9641 0.4269 0.077 Uiso 1 1 calc R . .
C27 C 0.26427(19) 0.9322(5) 0.4185(2) 0.0632(12) Uani 1 1 d . . .
H27 H 0.2805 0.8670 0.4583 0.076 Uiso 1 1 calc R . .
C28 C 0.06484(19) 1.1491(5) 0.2521(2) 0.0562(11) Uani 1 1 d . . .
C29 C 0.0161(2) 1.2557(6) 0.2286(3) 0.0853(15) Uani 1 1 d . . .
H29 H 0.0178 1.3350 0.2596 0.102 Uiso 1 1 calc R . .
C30 C -0.0350(2) 1.2460(7) 0.1599(3) 0.0936(17) Uani 1 1 d . . .
H30 H -0.0685 1.3162 0.1458 0.112 Uiso 1 1 calc R . .
C31 C -0.0367(2) 1.1351(6) 0.1130(3) 0.0787(15) Uani 1 1 d . . .
H31 H -0.0709 1.1299 0.0664 0.094 Uiso 1 1 calc R . .
C32 C 0.0120(2) 1.0305(6) 0.1342(2) 0.0705(13) Uani 1 1 d . . .
H32 H 0.0112 0.9552 0.1014 0.085 Uiso 1 1 calc R . .
C33 C 0.0627(2) 1.0360(5) 0.2045(2) 0.0586(11) Uani 1 1 d . . .
H33 H 0.0950 0.9631 0.2191 0.070 Uiso 1 1 calc R . .
C34 C 0.0935(2) 1.1788(5) 0.3855(2) 0.0601(11) Uani 1 1 d . . .
C35 C 0.0342(2) 1.1255(5) 0.3848(3) 0.0789(14) Uani 1 1 d . . .
H35 H 0.0051 1.0760 0.3433 0.095 Uiso 1 1 calc R . .
C36 C 0.0190(3) 1.1466(7) 0.4460(4) 0.107(2) Uani 1 1 d U . .
H36 H -0.0210 1.1114 0.4453 0.128 Uiso 1 1 calc R . .
C37 C 0.0606(4) 1.2173(8) 0.5073(4) 0.116(2) Uani 1 1 d U . .
H37 H 0.0497 1.2283 0.5486 0.140 Uiso 1 1 calc R . .
C38 C 0.1185(4) 1.2722(6) 0.5081(3) 0.103(2) Uani 1 1 d . . .
H38 H 0.1469 1.3225 0.5497 0.123 Uiso 1 1 calc R . .
C39 C 0.1354(3) 1.2537(5) 0.4473(3) 0.0746(13) Uani 1 1 d . . .
H39 H 0.1750 1.2917 0.4482 0.090 Uiso 1 1 calc R . .
C40 C 0.2063(2) 0.7647(5) 0.0991(2) 0.0704(13) Uani 1 1 d . . .
H40 H 0.2448 0.7460 0.1450 0.085 Uiso 1 1 calc R . .
Cl1 Cl 0.23213(8) 0.84833(17) 0.03368(8) 0.0986(5) Uani 1 1 d . . .
Cl2 Cl 0.15199(10) 0.8821(2) 0.11857(10) 0.1277(7) Uani 1 1 d . . .
Cl3 Cl 0.16666(10) 0.5994(2) 0.06514(9) 0.1271(7) Uani 1 1 d . . .
N1 N 0.74898(18) 0.3617(5) 0.7424(2) 0.0776(12) Uani 1 1 d . . .
N2 N 0.65224(18) 0.3285(5) 0.79351(19) 0.0720(11) Uani 1 1 d . . .
N3 N 0.59008(16) 0.6716(4) 0.54146(18) 0.0590(9) Uani 1 1 d U . .
N4 N 0.51242(15) 0.6417(4) 0.58780(18) 0.0556(9) Uani 1 1 d . . .
N5 N 0.11355(16) 1.1538(4) 0.32560(18) 0.0642(10) Uani 1 1 d . . .
S1 S 0.40451(5) 0.81174(14) 0.48479(6) 0.0646(4) 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
C1 N1 1.316(6) . ?
C1 C2 1.385(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.420(5) . ?
C4 C5 1.435(5) . ?
C5 C6 1.378(5) . ?
C5 N3 1.393(5) . ?
C6 N4 1.374(5) . ?
C6 C7 1.430(5) . ?
C7 C11 1.402(6) . ?
C7 C8 1.405(5) . ?
C8 C9 1.369(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(7) . ?
C9 H9 0.9300 . ?
C10 N2 1.327(6) . ?
C10 H10 0.9300 . ?
C11 N2 1.349(5) . ?
C11 C12 1.469(6) . ?
C12 N1 1.344(5) . ?
C13 N4 1.324(5) . ?
C13 N3 1.369(5) . ?
C13 C18 1.450(5) . ?
C14 C15 1.443(6) . ?
C14 N3 1.507(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.561(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.448(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.356(6) . ?
C18 S1 1.719(4) . ?
C19 C20 1.401(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.360(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.463(5) . ?
C21 S1 1.728(4) . ?
C22 C27 1.382(5) . ?
C22 C23 1.398(6) . ?
C23 C24 1.369(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.390(6) . ?
C24 H24 0.9300 . ?
C25 C26 1.374(6) . ?
C25 N5 1.419(5) . ?
C26 C27 1.372(5) . ?
C26 H26 0.9300 . ?
C27 H27 0.9300 . ?
C28 C33 1.371(6) . ?
C28 C29 1.382(6) . ?
C28 N5 1.420(5) . ?
C29 C30 1.379(7) . ?
C29 H29 0.9300 . ?
C30 C31 1.350(7) . ?
C30 H30 0.9300 . ?
C31 C32 1.368(6) . ?
C31 H31 0.9300 . ?
C32 C33 1.394(6) . ?
C32 H32 0.9300 . ?
C33 H33 0.9300 . ?
C34 C39 1.379(6) . ?
C34 C35 1.386(6) . ?
C34 N5 1.418(5) . ?
C35 C36 1.375(7) . ?
C35 H35 0.9300 . ?
C36 C37 1.353(9) . ?
C36 H36 0.9300 . ?
C37 C38 1.362(9) . ?
C37 H37 0.9300 . ?
C38 C39 1.384(7) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C40 Cl3 1.730(5) . ?
C40 Cl2 1.748(5) . ?
C40 Cl1 1.758(5) . ?
C40 H40 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.4(4) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.1(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C12 116.8(4) . . ?
C3 C4 C5 126.5(4) . . ?
C12 C4 C5 116.7(4) . . ?
C6 C5 N3 105.0(3) . . ?
C6 C5 C4 122.2(4) . . ?
N3 C5 C4 132.8(4) . . ?
N4 C6 C5 111.3(3) . . ?
N4 C6 C7 126.6(3) . . ?
C5 C6 C7 122.1(4) . . ?
C11 C7 C8 118.4(4) . . ?
C11 C7 C6 117.9(4) . . ?
C8 C7 C6 123.7(4) . . ?
C9 C8 C7 118.9(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 118.2(4) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 125.0(4) . . ?
N2 C10 H10 117.5 . . ?
C9 C10 H10 117.5 . . ?
N2 C11 C7 122.5(4) . . ?
N2 C11 C12 117.3(4) . . ?
C7 C11 C12 120.2(4) . . ?
N1 C12 C4 122.3(4) . . ?
N1 C12 C11 116.9(4) . . ?
C4 C12 C11 120.9(4) . . ?
N4 C13 N3 112.4(3) . . ?
N4 C13 C18 121.1(3) . . ?
N3 C13 C18 126.5(4) . . ?
C15 C14 N3 112.5(4) . . ?
C15 C14 H14A 109.1 . . ?
N3 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
N3 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 C16 109.9(5) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 117.1(7) . . ?
C17 C16 H16A 108.0 . . ?
C15 C16 H16A 108.0 . . ?
C17 C16 H16B 108.0 . . ?
C15 C16 H16B 108.0 . . ?
H16A C16 H16B 107.3 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C13 135.7(4) . . ?
C19 C18 S1 109.4(3) . . ?
C13 C18 S1 114.9(3) . . ?
C18 C19 C20 114.2(4) . . ?
C18 C19 H19 122.9 . . ?
C20 C19 H19 122.9 . . ?
C21 C20 C19 113.9(4) . . ?
C21 C20 H20 123.1 . . ?
C19 C20 H20 123.1 . . ?
C20 C21 C22 131.2(4) . . ?
C20 C21 S1 109.1(3) . . ?
C22 C21 S1 119.7(3) . . ?
C27 C22 C23 116.7(4) . . ?
C27 C22 C21 120.8(4) . . ?
C23 C22 C21 122.5(4) . . ?
C24 C23 C22 121.7(4) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 120.8(4) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 H24 119.6 . . ?
C26 C25 C24 117.6(4) . . ?
C26 C25 N5 120.7(4) . . ?
C24 C25 N5 121.7(4) . . ?
C27 C26 C25 121.6(4) . . ?
C27 C26 H26 119.2 . . ?
C25 C26 H26 119.2 . . ?
C26 C27 C22 121.5(4) . . ?
C26 C27 H27 119.2 . . ?
C22 C27 H27 119.2 . . ?
C33 C28 C29 118.6(4) . . ?
C33 C28 N5 121.5(4) . . ?
C29 C28 N5 119.9(4) . . ?
C30 C29 C28 120.8(5) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 H29 119.6 . . ?
C31 C30 C29 120.3(5) . . ?
C31 C30 H30 119.8 . . ?
C29 C30 H30 119.8 . . ?
C30 C31 C32 119.9(5) . . ?
C30 C31 H31 120.1 . . ?
C32 C31 H31 120.1 . . ?
C31 C32 C33 120.4(5) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C28 C33 C32 119.9(4) . . ?
C28 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C39 C34 C35 119.1(4) . . ?
C39 C34 N5 119.0(4) . . ?
C35 C34 N5 121.9(4) . . ?
C36 C35 C34 119.3(5) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C37 C36 C35 121.7(6) . . ?
C37 C36 H36 119.1 . . ?
C35 C36 H36 119.1 . . ?
C36 C37 C38 119.4(6) . . ?
C36 C37 H37 120.3 . . ?
C38 C37 H37 120.3 . . ?
C37 C38 C39 120.5(6) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C34 C39 C38 120.0(5) . . ?
C34 C39 H39 120.0 . . ?
C38 C39 H39 120.0 . . ?
Cl3 C40 Cl2 109.0(3) . . ?
Cl3 C40 Cl1 110.6(2) . . ?
Cl2 C40 Cl1 109.6(3) . . ?
Cl3 C40 H40 109.2 . . ?
Cl2 C40 H40 109.2 . . ?
Cl1 C40 H40 109.2 . . ?
C1 N1 C12 118.0(4) . . ?
C10 N2 C11 117.0(4) . . ?
C13 N3 C5 106.5(3) . . ?
C13 N3 C14 125.0(4) . . ?
C5 N3 C14 127.1(3) . . ?
C13 N4 C6 104.8(3) . . ?
C34 N5 C25 117.9(3) . . ?
C34 N5 C28 119.0(3) . . ?
C25 N5 C28 120.0(3) . . ?
C18 S1 C21 93.33(19) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.057
####################################################################### 
# 
# 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_9
_database_code_depnum_ccdc_archive 'CCDC 1018240'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H30 Cl3 N5 S'
_chemical_formula_sum            'C40 H30 Cl3 N5 S'
_chemical_formula_weight         719.10

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'


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

_cell_length_a                   12.4041(19)
_cell_length_b                   12.4543(19)
_cell_length_c                   13.762(2)
_cell_angle_alpha                111.741(2)
_cell_angle_beta                 100.880(3)
_cell_angle_gamma                110.123(2)
_cell_volume                     1728.2(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    6017
_cell_measurement_theta_min      2.505
_cell_measurement_theta_max      25.683

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             744
_exptl_absorpt_coefficient_mu    0.364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9715
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12888
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6017
_reflns_number_gt                4223
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1027P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6017
_refine_ls_number_parameters     471
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1743
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.4069(3) 0.1709(3) 0.2538(3) 0.0625(8) Uani 1 1 d . . .
H1 H -0.4818 0.1046 0.2393 0.075 Uiso 1 1 calc R . .
C2 C -0.4098(3) 0.2664(3) 0.2246(3) 0.0676(8) Uani 1 1 d . . .
H2 H -0.4843 0.2639 0.1926 0.081 Uiso 1 1 calc R . .
C3 C -0.3012(2) 0.3627(3) 0.2443(3) 0.0586(7) Uani 1 1 d . . .
H3 H -0.2998 0.4277 0.2259 0.070 Uiso 1 1 calc R . .
C4 C -0.1918(2) 0.3631(2) 0.2925(2) 0.0480(6) Uani 1 1 d . . .
C5 C -0.0720(2) 0.4605(2) 0.3168(2) 0.0467(6) Uani 1 1 d . . .
C6 C 0.0338(2) 0.4596(2) 0.3676(2) 0.0422(6) Uani 1 1 d . . .
C7 C 0.0332(2) 0.3610(2) 0.3973(2) 0.0428(6) Uani 1 1 d . . .
C8 C 0.1353(2) 0.3484(3) 0.4449(2) 0.0508(6) Uani 1 1 d . . .
H8 H 0.2143 0.4092 0.4609 0.061 Uiso 1 1 calc R . .
C9 C 0.1204(3) 0.2480(3) 0.4681(2) 0.0589(7) Uani 1 1 d . . .
H9 H 0.1881 0.2397 0.5001 0.071 Uiso 1 1 calc R . .
C10 C 0.0013(3) 0.1585(3) 0.4427(2) 0.0592(7) Uani 1 1 d . . .
H10 H -0.0085 0.0911 0.4598 0.071 Uiso 1 1 calc R . .
C11 C -0.0839(2) 0.2628(2) 0.3730(2) 0.0449(6) Uani 1 1 d . . .
C12 C -0.1971(2) 0.2648(2) 0.3207(2) 0.0464(6) Uani 1 1 d . . .
C13 C 0.0729(2) 0.6259(2) 0.3329(2) 0.0457(6) Uani 1 1 d . . .
C14 C 0.1351(2) 0.7404(2) 0.3208(2) 0.0488(6) Uani 1 1 d . . .
C15 C 0.2493(3) 0.8019(3) 0.3212(3) 0.0600(8) Uani 1 1 d . . .
H15 H 0.3120 0.7797 0.3384 0.072 Uiso 1 1 calc R . .
C16 C 0.2638(2) 0.9014(3) 0.2934(3) 0.0566(7) Uani 1 1 d . . .
H16 H 0.3370 0.9516 0.2900 0.068 Uiso 1 1 calc R . .
C17 C 0.1604(2) 0.9182(2) 0.2716(2) 0.0449(6) Uani 1 1 d . . .
C18 C 0.1379(2) 1.0072(2) 0.2341(2) 0.0436(6) Uani 1 1 d . . .
C19 C 0.2339(2) 1.1065(2) 0.2327(2) 0.0494(6) Uani 1 1 d . . .
H19 H 0.3141 1.1195 0.2614 0.059 Uiso 1 1 calc R . .
C20 C 0.2146(2) 1.1854(2) 0.1907(2) 0.0495(6) Uani 1 1 d . . .
H20 H 0.2803 1.2519 0.1924 0.059 Uiso 1 1 calc R . .
C21 C 0.0942(2) 1.1630(2) 0.1456(2) 0.0433(6) Uani 1 1 d . . .
C22 C -0.0034(2) 1.0681(2) 0.1497(2) 0.0425(6) Uani 1 1 d . . .
C23 C 0.0193(2) 0.9904(2) 0.1937(2) 0.0436(6) Uani 1 1 d . . .
H23 H -0.0457 0.9270 0.1960 0.052 Uiso 1 1 calc R . .
C24 C -0.1151(2) 1.0710(2) 0.1007(2) 0.0442(6) Uani 1 1 d . . .
C25 C -0.0812(2) 1.1662(2) 0.0666(2) 0.0476(6) Uani 1 1 d . . .
C26 C -0.1698(3) 1.1896(3) 0.0100(2) 0.0589(7) Uani 1 1 d . . .
H26 H -0.1478 1.2518 -0.0142 0.071 Uiso 1 1 calc R . .
C27 C -0.2888(3) 1.1178(3) -0.0079(3) 0.0655(8) Uani 1 1 d . . .
H27 H -0.3494 1.1315 -0.0452 0.079 Uiso 1 1 calc R . .
C28 C -0.3240(3) 1.0244(3) 0.0274(2) 0.0618(8) Uani 1 1 d . . .
H28 H -0.4067 0.9778 0.0143 0.074 Uiso 1 1 calc R . .
C29 C -0.2378(2) 1.0005(3) 0.0811(2) 0.0527(7) Uani 1 1 d . . .
H29 H -0.2614 0.9376 0.1042 0.063 Uiso 1 1 calc R . .
C30 C 0.1143(2) 1.3212(2) 0.0699(2) 0.0509(7) Uani 1 1 d . . .
C31 C 0.2031(3) 1.3118(3) 0.0253(3) 0.0655(8) Uani 1 1 d . . .
H31 H 0.2198 1.2415 0.0123 0.079 Uiso 1 1 calc R . .
C32 C 0.2670(3) 1.4051(3) -0.0002(3) 0.0854(11) Uani 1 1 d . . .
H32 H 0.3278 1.3991 -0.0292 0.102 Uiso 1 1 calc R . .
C33 C 0.2401(4) 1.5094(4) 0.0178(4) 0.1000(14) Uani 1 1 d . . .
H33 H 0.2814 1.5718 -0.0014 0.120 Uiso 1 1 calc R . .
C34 C 0.1531(4) 1.5202(3) 0.0636(3) 0.0858(12) Uani 1 1 d . . .
H34 H 0.1363 1.5904 0.0766 0.103 Uiso 1 1 calc R . .
C35 C 0.0903(3) 1.4265(3) 0.0907(2) 0.0645(8) Uani 1 1 d . . .
H35 H 0.0319 1.4343 0.1227 0.077 Uiso 1 1 calc R . .
C36 C 0.2605(2) 0.6210(2) 0.4376(2) 0.0463(6) Uani 1 1 d . . .
H36A H 0.2729 0.6059 0.5022 0.056 Uiso 1 1 calc R . .
H36B H 0.2996 0.7140 0.4650 0.056 Uiso 1 1 calc R . .
C37 C 0.3224(2) 0.5616(2) 0.3646(2) 0.0511(6) Uani 1 1 d . . .
H37A H 0.3143 0.5810 0.3023 0.061 Uiso 1 1 calc R . .
H37B H 0.2807 0.4681 0.3339 0.061 Uiso 1 1 calc R . .
C38 C 0.4580(3) 0.6111(3) 0.4280(3) 0.0782(10) Uani 1 1 d . . .
H38A H 0.4996 0.7047 0.4593 0.094 Uiso 1 1 calc R . .
H38B H 0.4661 0.5909 0.4898 0.094 Uiso 1 1 calc R . .
C39 C 0.5193(3) 0.5528(4) 0.3548(4) 0.1094(15) Uani 1 1 d . . .
H39A H 0.4863 0.4618 0.3322 0.164 Uiso 1 1 calc R . .
H39B H 0.6064 0.5945 0.3958 0.164 Uiso 1 1 calc R . .
H39C H 0.5045 0.5650 0.2895 0.164 Uiso 1 1 calc R . .
C40 C 0.6588(3) 0.9025(3) 0.3030(3) 0.0713(9) Uani 1 1 d . . .
H40 H 0.6923 0.9827 0.3027 0.086 Uiso 1 1 d R A .
N1 N -0.30605(19) 0.1681(2) 0.3001(2) 0.0540(6) Uani 1 1 d . . .
N2 N -0.0980(2) 0.1634(2) 0.39592(19) 0.0526(6) Uani 1 1 d . . .
N3 N 0.12888(17) 0.56954(18) 0.37983(17) 0.0438(5) Uani 1 1 d . . .
N4 N -0.04762(19) 0.5633(2) 0.29531(19) 0.0504(5) Uani 1 1 d . . .
N5 N 0.04656(19) 1.22355(19) 0.09506(18) 0.0481(5) Uani 1 1 d . . .
S1 S 0.04392(6) 0.80630(7) 0.28398(7) 0.0570(2) Uani 1 1 d . . .
Cl1 Cl 0.5196(3) 0.8083(4) 0.1915(3) 0.1168(12) Uani 0.711(11) 1 d P A 1
Cl2 Cl 0.6464(6) 0.9383(3) 0.4333(3) 0.1394(16) Uani 0.711(11) 1 d P A 1
Cl3 Cl 0.7535(3) 0.8194(3) 0.28936(19) 0.0882(9) Uani 0.711(11) 1 d P A 1
Cl1' Cl 0.5409(14) 0.8164(14) 0.1846(15) 0.259(10) Uani 0.289(11) 1 d P A 2
Cl2' Cl 0.5816(14) 0.9230(13) 0.3953(14) 0.205(6) Uani 0.289(11) 1 d P A 2
Cl3' Cl 0.7286(11) 0.8294(12) 0.3087(16) 0.250(8) Uani 0.289(11) 1 d P A 2


_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
C1 N1 1.310(3) . ?
C1 C2 1.398(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.356(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.400(3) . ?
C4 C5 1.436(3) . ?
C5 N4 1.366(3) . ?
C5 C6 1.372(3) . ?
C6 N3 1.392(3) . ?
C6 C7 1.429(3) . ?
C7 C8 1.399(3) . ?
C7 C11 1.417(3) . ?
C8 C9 1.363(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.389(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.310(3) . ?
C10 H10 0.9300 . ?
C11 N2 1.351(3) . ?
C11 C12 1.465(3) . ?
C12 N1 1.356(3) . ?
C13 N4 1.310(3) . ?
C13 N3 1.376(3) . ?
C13 C14 1.457(3) . ?
C14 C15 1.358(4) . ?
C14 S1 1.715(2) . ?
C15 C16 1.391(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.365(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.469(3) . ?
C17 S1 1.716(3) . ?
C18 C23 1.382(3) . ?
C18 C19 1.400(3) . ?
C19 C20 1.374(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9300 . ?
C21 N5 1.393(3) . ?
C21 C22 1.398(3) . ?
C22 C23 1.392(3) . ?
C22 C24 1.441(3) . ?
C23 H23 0.9300 . ?
C24 C29 1.382(4) . ?
C24 C25 1.395(3) . ?
C25 N5 1.399(3) . ?
C25 C26 1.401(3) . ?
C26 C27 1.353(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.388(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.364(4) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?
C30 C31 1.377(4) . ?
C30 C35 1.383(4) . ?
C30 N5 1.422(3) . ?
C31 C32 1.369(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.398(6) . ?
C32 H32 0.9300 . ?
C33 C34 1.369(6) . ?
C33 H33 0.9300 . ?
C34 C35 1.383(5) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 N3 1.456(3) . ?
C36 C37 1.509(4) . ?
C36 H36A 0.9700 . ?
C36 H36B 0.9700 . ?
C37 C38 1.518(4) . ?
C37 H37A 0.9700 . ?
C37 H37B 0.9700 . ?
C38 C39 1.499(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C40 Cl3' 1.467(12) . ?
C40 Cl1' 1.634(14) . ?
C40 Cl2' 1.726(12) . ?
C40 Cl1 1.727(4) . ?
C40 Cl2 1.731(4) . ?
C40 Cl3 1.806(4) . ?
C40 H40 0.9424 . ?

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
N1 C1 C2 124.6(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C2 C3 C4 119.1(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C12 119.0(2) . . ?
C3 C4 C5 123.6(2) . . ?
C12 C4 C5 117.5(2) . . ?
N4 C5 C6 111.9(2) . . ?
N4 C5 C4 126.3(2) . . ?
C6 C5 C4 121.8(2) . . ?
C5 C6 N3 104.7(2) . . ?
C5 C6 C7 122.8(2) . . ?
N3 C6 C7 132.4(2) . . ?
C8 C7 C11 116.3(2) . . ?
C8 C7 C6 127.2(2) . . ?
C11 C7 C6 116.5(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 118.2(3) . . ?
C8 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
N2 C10 C9 124.0(2) . . ?
N2 C10 H10 118.0 . . ?
C9 C10 H10 118.0 . . ?
N2 C11 C7 122.7(2) . . ?
N2 C11 C12 116.5(2) . . ?
C7 C11 C12 120.8(2) . . ?
N1 C12 C4 121.7(2) . . ?
N1 C12 C11 117.7(2) . . ?
C4 C12 C11 120.6(2) . . ?
N4 C13 N3 112.8(2) . . ?
N4 C13 C14 121.1(2) . . ?
N3 C13 C14 126.2(2) . . ?
C15 C14 C13 134.1(2) . . ?
C15 C14 S1 110.03(18) . . ?
C13 C14 S1 115.52(18) . . ?
C14 C15 C16 113.7(2) . . ?
C14 C15 H15 123.1 . . ?
C16 C15 H15 123.1 . . ?
C17 C16 C15 113.7(2) . . ?
C17 C16 H16 123.2 . . ?
C15 C16 H16 123.2 . . ?
C16 C17 C18 129.6(2) . . ?
C16 C17 S1 109.71(18) . . ?
C18 C17 S1 120.51(18) . . ?
C23 C18 C19 118.3(2) . . ?
C23 C18 C17 120.3(2) . . ?
C19 C18 C17 121.3(2) . . ?
C20 C19 C18 122.7(2) . . ?
C20 C19 H19 118.6 . . ?
C18 C19 H19 118.6 . . ?
C19 C20 C21 118.1(2) . . ?
C19 C20 H20 120.9 . . ?
C21 C20 H20 120.9 . . ?
C20 C21 N5 131.1(2) . . ?
C20 C21 C22 120.5(2) . . ?
N5 C21 C22 108.4(2) . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 C24 132.4(2) . . ?
C21 C22 C24 107.7(2) . . ?
C18 C23 C22 120.3(2) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C29 C24 C25 119.6(2) . . ?
C29 C24 C22 133.9(2) . . ?
C25 C24 C22 106.5(2) . . ?
C24 C25 N5 109.2(2) . . ?
C24 C25 C26 121.2(2) . . ?
N5 C25 C26 129.6(2) . . ?
C27 C26 C25 117.1(3) . . ?
C27 C26 H26 121.5 . . ?
C25 C26 H26 121.5 . . ?
C26 C27 C28 122.5(3) . . ?
C26 C27 H27 118.7 . . ?
C28 C27 H27 118.7 . . ?
C29 C28 C27 120.3(3) . . ?
C29 C28 H28 119.9 . . ?
C27 C28 H28 119.9 . . ?
C28 C29 C24 119.3(3) . . ?
C28 C29 H29 120.4 . . ?
C24 C29 H29 120.4 . . ?
C31 C30 C35 119.9(3) . . ?
C31 C30 N5 120.7(2) . . ?
C35 C30 N5 119.4(3) . . ?
C32 C31 C30 120.5(3) . . ?
C32 C31 H31 119.7 . . ?
C30 C31 H31 119.7 . . ?
C31 C32 C33 119.4(4) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C34 C33 C32 120.2(3) . . ?
C34 C33 H33 119.9 . . ?
C32 C33 H33 119.9 . . ?
C33 C34 C35 120.0(3) . . ?
C33 C34 H34 120.0 . . ?
C35 C34 H34 120.0 . . ?
C34 C35 C30 119.9(3) . . ?
C34 C35 H35 120.0 . . ?
C30 C35 H35 120.0 . . ?
N3 C36 C37 113.6(2) . . ?
N3 C36 H36A 108.9 . . ?
C37 C36 H36A 108.9 . . ?
N3 C36 H36B 108.9 . . ?
C37 C36 H36B 108.9 . . ?
H36A C36 H36B 107.7 . . ?
C36 C37 C38 112.7(2) . . ?
C36 C37 H37A 109.0 . . ?
C38 C37 H37A 109.0 . . ?
C36 C37 H37B 109.0 . . ?
C38 C37 H37B 109.0 . . ?
H37A C37 H37B 107.8 . . ?
C39 C38 C37 112.5(3) . . ?
C39 C38 H38A 109.1 . . ?
C37 C38 H38A 109.1 . . ?
C39 C38 H38B 109.1 . . ?
C37 C38 H38B 109.1 . . ?
H38A C38 H38B 107.8 . . ?
C38 C39 H39A 109.5 . . ?
C38 C39 H39B 109.5 . . ?
H39A C39 H39B 109.5 . . ?
C38 C39 H39C 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
Cl3' C40 Cl1' 109.2(8) . . ?
Cl3' C40 Cl2' 116.0(7) . . ?
Cl1' C40 Cl2' 99.3(8) . . ?
Cl3' C40 Cl1 111.9(6) . . ?
Cl1' C40 Cl1 9.6(8) . . ?
Cl2' C40 Cl1 89.9(6) . . ?
Cl3' C40 Cl2 96.3(7) . . ?
Cl1' C40 Cl2 123.9(7) . . ?
Cl2' C40 Cl2 26.3(5) . . ?
Cl1 C40 Cl2 114.3(3) . . ?
Cl3' C40 Cl3 11.2(8) . . ?
Cl1' C40 Cl3 105.3(7) . . ?
Cl2' C40 Cl3 127.1(6) . . ?
Cl1 C40 Cl3 109.8(2) . . ?
Cl2 C40 Cl3 106.7(3) . . ?
Cl3' C40 H40 123.0 . . ?
Cl1' C40 H40 100.8 . . ?
Cl2' C40 H40 105.2 . . ?
Cl1 C40 H40 105.6 . . ?
Cl2 C40 H40 105.7 . . ?
Cl3 C40 H40 114.9 . . ?
C1 N1 C12 117.4(2) . . ?
C10 N2 C11 118.1(2) . . ?
C13 N3 C6 105.92(19) . . ?
C13 N3 C36 126.4(2) . . ?
C6 N3 C36 127.53(19) . . ?
C13 N4 C5 104.6(2) . . ?
C21 N5 C25 108.2(2) . . ?
C21 N5 C30 126.3(2) . . ?
C25 N5 C30 125.4(2) . . ?
C14 S1 C17 92.85(12) . . ?

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
N1 C1 C2 C3 0.7(5) . . . . ?
C1 C2 C3 C4 -0.1(5) . . . . ?
C2 C3 C4 C12 -0.9(4) . . . . ?
C2 C3 C4 C5 180.0(3) . . . . ?
C3 C4 C5 N4 -1.1(4) . . . . ?
C12 C4 C5 N4 179.7(2) . . . . ?
C3 C4 C5 C6 177.9(3) . . . . ?
C12 C4 C5 C6 -1.2(4) . . . . ?
N4 C5 C6 N3 1.1(3) . . . . ?
C4 C5 C6 N3 -178.1(2) . . . . ?
N4 C5 C6 C7 -179.1(2) . . . . ?
C4 C5 C6 C7 1.7(4) . . . . ?
C5 C6 C7 C8 177.2(2) . . . . ?
N3 C6 C7 C8 -3.0(5) . . . . ?
C5 C6 C7 C11 -0.9(4) . . . . ?
N3 C6 C7 C11 178.9(2) . . . . ?
C11 C7 C8 C9 -1.4(4) . . . . ?
C6 C7 C8 C9 -179.5(3) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C9 C10 N2 1.2(5) . . . . ?
C8 C7 C11 N2 1.3(4) . . . . ?
C6 C7 C11 N2 179.5(2) . . . . ?
C8 C7 C11 C12 -178.6(2) . . . . ?
C6 C7 C11 C12 -0.3(4) . . . . ?
C3 C4 C12 N1 1.3(4) . . . . ?
C5 C4 C12 N1 -179.4(2) . . . . ?
C3 C4 C12 C11 -179.2(2) . . . . ?
C5 C4 C12 C11 0.1(4) . . . . ?
N2 C11 C12 N1 0.4(3) . . . . ?
C7 C11 C12 N1 -179.8(2) . . . . ?
N2 C11 C12 C4 -179.2(2) . . . . ?
C7 C11 C12 C4 0.7(4) . . . . ?
N4 C13 C14 C15 -158.4(3) . . . . ?
N3 C13 C14 C15 19.9(5) . . . . ?
N4 C13 C14 S1 13.6(3) . . . . ?
N3 C13 C14 S1 -168.1(2) . . . . ?
C13 C14 C15 C16 172.9(3) . . . . ?
S1 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -176.4(3) . . . . ?
C15 C16 C17 S1 -1.0(3) . . . . ?
C16 C17 C18 C23 166.1(3) . . . . ?
S1 C17 C18 C23 -8.9(3) . . . . ?
C16 C17 C18 C19 -10.7(4) . . . . ?
S1 C17 C18 C19 174.4(2) . . . . ?
C23 C18 C19 C20 -1.5(4) . . . . ?
C17 C18 C19 C20 175.3(3) . . . . ?
C18 C19 C20 C21 -1.5(4) . . . . ?
C19 C20 C21 N5 -178.0(3) . . . . ?
C19 C20 C21 C22 4.0(4) . . . . ?
C20 C21 C22 C23 -3.5(4) . . . . ?
N5 C21 C22 C23 178.1(2) . . . . ?
C20 C21 C22 C24 177.9(2) . . . . ?
N5 C21 C22 C24 -0.5(3) . . . . ?
C19 C18 C23 C22 2.1(4) . . . . ?
C17 C18 C23 C22 -174.8(2) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?
C24 C22 C23 C18 178.6(2) . . . . ?
C23 C22 C24 C29 0.9(5) . . . . ?
C21 C22 C24 C29 179.3(3) . . . . ?
C23 C22 C24 C25 -177.3(3) . . . . ?
C21 C22 C24 C25 1.1(3) . . . . ?
C29 C24 C25 N5 -179.8(2) . . . . ?
C22 C24 C25 N5 -1.3(3) . . . . ?
C29 C24 C25 C26 -1.7(4) . . . . ?
C22 C24 C25 C26 176.8(2) . . . . ?
C24 C25 C26 C27 1.3(4) . . . . ?
N5 C25 C26 C27 179.0(3) . . . . ?
C25 C26 C27 C28 -0.1(4) . . . . ?
C26 C27 C28 C29 -0.8(5) . . . . ?
C27 C28 C29 C24 0.4(4) . . . . ?
C25 C24 C29 C28 0.8(4) . . . . ?
C22 C24 C29 C28 -177.2(3) . . . . ?
C35 C30 C31 C32 -0.8(5) . . . . ?
N5 C30 C31 C32 179.2(3) . . . . ?
C30 C31 C32 C33 -1.0(5) . . . . ?
C31 C32 C33 C34 1.9(6) . . . . ?
C32 C33 C34 C35 -1.0(6) . . . . ?
C33 C34 C35 C30 -0.9(5) . . . . ?
C31 C30 C35 C34 1.8(4) . . . . ?
N5 C30 C35 C34 -178.2(2) . . . . ?
N3 C36 C37 C38 -176.9(2) . . . . ?
C36 C37 C38 C39 -179.4(3) . . . . ?
C2 C1 N1 C12 -0.2(4) . . . . ?
C4 C12 N1 C1 -0.8(4) . . . . ?
C11 C12 N1 C1 179.7(2) . . . . ?
C9 C10 N2 C11 -1.3(4) . . . . ?
C7 C11 N2 C10 0.1(4) . . . . ?
C12 C11 N2 C10 180.0(2) . . . . ?
N4 C13 N3 C6 1.6(3) . . . . ?
C14 C13 N3 C6 -176.8(2) . . . . ?
N4 C13 N3 C36 -174.3(2) . . . . ?
C14 C13 N3 C36 7.3(4) . . . . ?
C5 C6 N3 C13 -1.6(3) . . . . ?
C7 C6 N3 C13 178.6(3) . . . . ?
C5 C6 N3 C36 174.3(2) . . . . ?
C7 C6 N3 C36 -5.5(4) . . . . ?
C37 C36 N3 C13 -98.5(3) . . . . ?
C37 C36 N3 C6 86.4(3) . . . . ?
N3 C13 N4 C5 -1.0(3) . . . . ?
C14 C13 N4 C5 177.5(2) . . . . ?
C6 C5 N4 C13 -0.1(3) . . . . ?
C4 C5 N4 C13 179.1(3) . . . . ?
C20 C21 N5 C25 -178.5(3) . . . . ?
C22 C21 N5 C25 -0.3(3) . . . . ?
C20 C21 N5 C30 5.1(4) . . . . ?
C22 C21 N5 C30 -176.7(2) . . . . ?
C24 C25 N5 C21 1.1(3) . . . . ?
C26 C25 N5 C21 -176.8(3) . . . . ?
C24 C25 N5 C30 177.5(2) . . . . ?
C26 C25 N5 C30 -0.4(4) . . . . ?
C31 C30 N5 C21 42.3(4) . . . . ?
C35 C30 N5 C21 -137.7(3) . . . . ?
C31 C30 N5 C25 -133.5(3) . . . . ?
C35 C30 N5 C25 46.5(4) . . . . ?
C15 C14 S1 C17 -1.0(2) . . . . ?
C13 C14 S1 C17 -174.9(2) . . . . ?
C16 C17 S1 C14 1.1(2) . . . . ?
C18 C17 S1 C14 177.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.272
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.081
####################################################################### 
# 
# 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_10
_database_code_depnum_ccdc_archive 'CCDC 1018241'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H20 N4 S2'
_chemical_formula_sum            'C25 H20 N4 S2'
_chemical_formula_weight         440.57

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   13.596(4)
_cell_length_b                   8.610(3)
_cell_length_c                   19.250(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.600(4)
_cell_angle_gamma                90.00
_cell_volume                     2065.0(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3627
_cell_measurement_theta_min      2.308
_cell_measurement_theta_max      27.448

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    0.279
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9726
_exptl_absorpt_correction_T_max  0.9780
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14339
_diffrn_reflns_av_R_equivalents  0.1129
_diffrn_reflns_av_sigmaI/netI    0.0898
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.63
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3627
_reflns_number_gt                2240
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0944P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3627
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1086
_refine_ls_R_factor_gt           0.0617
_refine_ls_wR_factor_ref         0.1749
_refine_ls_wR_factor_gt          0.1551
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.9988(3) 0.6514(5) 0.5634(2) 0.0528(11) Uani 1 1 d . . .
H1 H 1.0634 0.7041 0.5760 0.063 Uiso 1 1 calc R . .
C2 C 0.9868(3) 0.5620(5) 0.6184(2) 0.0544(11) Uani 1 1 d . . .
H2 H 1.0420 0.5536 0.6663 0.065 Uiso 1 1 calc R . .
C3 C 0.8929(3) 0.4863(5) 0.6017(2) 0.0502(10) Uani 1 1 d . . .
H3 H 0.8828 0.4264 0.6385 0.060 Uiso 1 1 calc R . .
C4 C 0.8108(3) 0.4978(4) 0.52898(19) 0.0372(8) Uani 1 1 d . . .
C5 C 0.7055(3) 0.4268(4) 0.50311(19) 0.0339(8) Uani 1 1 d . . .
C6 C 0.6297(3) 0.4473(4) 0.43088(19) 0.0354(8) Uani 1 1 d . . .
C7 C 0.6510(3) 0.5369(4) 0.3763(2) 0.0376(9) Uani 1 1 d . . .
C8 C 0.5757(3) 0.5590(5) 0.3022(2) 0.0480(10) Uani 1 1 d . . .
H8 H 0.5086 0.5122 0.2858 0.058 Uiso 1 1 calc R . .
C9 C 0.6022(3) 0.6507(5) 0.2541(2) 0.0572(11) Uani 1 1 d . . .
H9 H 0.5538 0.6677 0.2045 0.069 Uiso 1 1 calc R . .
C10 C 0.7039(4) 0.7175(5) 0.2820(2) 0.0582(11) Uani 1 1 d . . .
H10 H 0.7213 0.7807 0.2494 0.070 Uiso 1 1 calc R . .
C11 C 0.7520(3) 0.6099(4) 0.3990(2) 0.0388(9) Uani 1 1 d . . .
C12 C 0.8317(3) 0.5897(4) 0.4763(2) 0.0383(9) Uani 1 1 d . . .
C13 C 0.5539(3) 0.3112(4) 0.48697(19) 0.0355(8) Uani 1 1 d . . .
C14 C 0.4697(3) 0.2255(4) 0.4986(2) 0.0368(8) Uani 1 1 d . . .
C15 C 0.4599(3) 0.1542(5) 0.5596(2) 0.0482(10) Uani 1 1 d . . .
H15 H 0.5144 0.1506 0.6080 0.058 Uiso 1 1 calc R . .
C16 C 0.3575(3) 0.0872(5) 0.5399(2) 0.0518(11) Uani 1 1 d . . .
H16 H 0.3378 0.0351 0.5747 0.062 Uiso 1 1 calc R . .
C17 C 0.2905(3) 0.1052(4) 0.4664(2) 0.0379(9) Uani 1 1 d . . .
C18 C 0.1804(3) 0.0459(4) 0.4269(2) 0.0406(9) Uani 1 1 d . . .
C19 C 0.1150(3) 0.0663(4) 0.3477(2) 0.0470(10) Uani 1 1 d . . .
H19 H 0.1335 0.1225 0.3135 0.056 Uiso 1 1 calc R . .
C20 C 0.0160(3) -0.0152(5) 0.3307(3) 0.0626(12) Uani 1 1 d . . .
H20 H -0.0390 -0.0166 0.2825 0.075 Uiso 1 1 calc R . .
C21 C 0.0090(3) -0.0900(5) 0.3906(3) 0.0629(12) Uani 1 1 d . . .
H21 H -0.0502 -0.1480 0.3879 0.076 Uiso 1 1 calc R . .
C22 C 0.7057(3) 0.2636(4) 0.61482(19) 0.0417(9) Uani 1 1 d . . .
H22A H 0.7810 0.2443 0.6268 0.050 Uiso 1 1 calc R . .
H22B H 0.6715 0.1641 0.6133 0.050 Uiso 1 1 calc R . .
C23 C 0.6965(3) 0.3603(5) 0.67671(19) 0.0447(9) Uani 1 1 d . . .
H23A H 0.6220 0.3885 0.6633 0.054 Uiso 1 1 calc R . .
H23B H 0.7378 0.4550 0.6830 0.054 Uiso 1 1 calc R . .
C24 C 0.7386(4) 0.2681(5) 0.7513(2) 0.0615(12) Uani 1 1 d . . .
H24A H 0.7008 0.1697 0.7429 0.074 Uiso 1 1 calc R . .
H24B H 0.8141 0.2456 0.7653 0.074 Uiso 1 1 calc R . .
C25 C 0.7263(4) 0.3500(6) 0.8160(2) 0.0678(13) Uani 1 1 d . . .
H25A H 0.7691 0.4427 0.8280 0.102 Uiso 1 1 calc R . .
H25B H 0.7495 0.2829 0.8594 0.102 Uiso 1 1 calc R . .
H25C H 0.6522 0.3770 0.8019 0.102 Uiso 1 1 calc R . .
N1 N 0.9257(2) 0.6677(4) 0.49420(18) 0.0465(8) Uani 1 1 d . . .
N2 N 0.7772(3) 0.6979(4) 0.35100(19) 0.0533(9) Uani 1 1 d . . .
N3 N 0.6566(2) 0.3366(3) 0.53892(15) 0.0343(7) Uani 1 1 d . . .
N4 N 0.5361(2) 0.3768(3) 0.42101(16) 0.0390(7) Uani 1 1 d . . .
S1 S 0.35215(7) 0.20587(12) 0.41846(5) 0.0445(3) Uani 1 1 d . . .
S2 S 0.12054(9) -0.06505(14) 0.47050(7) 0.0607(4) 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
C1 N1 1.312(5) . ?
C1 C2 1.371(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.352(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.401(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.403(5) . ?
C4 C5 1.449(4) . ?
C5 C6 1.371(5) . ?
C5 N3 1.374(4) . ?
C6 N4 1.353(4) . ?
C6 C7 1.424(5) . ?
C7 C8 1.395(5) . ?
C7 C11 1.412(5) . ?
C8 C9 1.370(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.392(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.314(5) . ?
C10 H10 0.9300 . ?
C11 N2 1.341(5) . ?
C11 C12 1.458(5) . ?
C12 N1 1.361(4) . ?
C13 N4 1.320(4) . ?
C13 N3 1.371(4) . ?
C13 C14 1.452(5) . ?
C14 C15 1.377(5) . ?
C14 S1 1.729(4) . ?
C15 C16 1.412(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.351(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.472(5) . ?
C17 S1 1.710(4) . ?
C18 C19 1.434(5) . ?
C18 S2 1.682(4) . ?
C19 C20 1.434(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(6) . ?
C20 H20 0.9300 . ?
C21 S2 1.687(4) . ?
C21 H21 0.9300 . ?
C22 N3 1.481(4) . ?
C22 C23 1.499(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.536(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.498(6) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
N1 C1 C2 124.6(4) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 120.2(4) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C12 116.8(3) . . ?
C3 C4 C5 126.6(3) . . ?
C12 C4 C5 116.6(3) . . ?
C6 C5 N3 105.3(3) . . ?
C6 C5 C4 122.2(3) . . ?
N3 C5 C4 132.5(3) . . ?
N4 C6 C5 111.6(3) . . ?
N4 C6 C7 126.7(3) . . ?
C5 C6 C7 121.7(3) . . ?
C8 C7 C11 118.7(3) . . ?
C8 C7 C6 123.0(3) . . ?
C11 C7 C6 118.2(3) . . ?
C9 C8 C7 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C8 C9 C10 117.8(4) . . ?
C8 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
N2 C10 C9 124.8(4) . . ?
N2 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
N2 C11 C7 121.6(3) . . ?
N2 C11 C12 118.7(3) . . ?
C7 C11 C12 119.8(3) . . ?
N1 C12 C4 122.5(3) . . ?
N1 C12 C11 116.0(3) . . ?
C4 C12 C11 121.5(3) . . ?
N4 C13 N3 112.0(3) . . ?
N4 C13 C14 120.9(3) . . ?
N3 C13 C14 127.1(3) . . ?
C15 C14 C13 135.1(3) . . ?
C15 C14 S1 110.3(3) . . ?
C13 C14 S1 114.6(3) . . ?
C14 C15 C16 112.1(3) . . ?
C14 C15 H15 124.0 . . ?
C16 C15 H15 124.0 . . ?
C17 C16 C15 114.4(4) . . ?
C17 C16 H16 122.8 . . ?
C15 C16 H16 122.8 . . ?
C16 C17 C18 128.4(3) . . ?
C16 C17 S1 110.6(3) . . ?
C18 C17 S1 120.9(3) . . ?
C19 C18 C17 125.2(3) . . ?
C19 C18 S2 112.4(3) . . ?
C17 C18 S2 122.3(3) . . ?
C18 C19 C20 108.0(3) . . ?
C18 C19 H19 126.0 . . ?
C20 C19 H19 126.0 . . ?
C21 C20 C19 114.7(4) . . ?
C21 C20 H20 122.7 . . ?
C19 C20 H20 122.7 . . ?
C20 C21 S2 111.7(3) . . ?
C20 C21 H21 124.1 . . ?
S2 C21 H21 124.1 . . ?
N3 C22 C23 113.6(3) . . ?
N3 C22 H22A 108.8 . . ?
C23 C22 H22A 108.8 . . ?
N3 C22 H22B 108.8 . . ?
C23 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 C24 109.7(3) . . ?
C22 C23 H23A 109.7 . . ?
C24 C23 H23A 109.7 . . ?
C22 C23 H23B 109.7 . . ?
C24 C23 H23B 109.7 . . ?
H23A C23 H23B 108.2 . . ?
C25 C24 C23 114.2(4) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 N1 C12 117.2(3) . . ?
C10 N2 C11 118.0(3) . . ?
C13 N3 C5 106.3(3) . . ?
C13 N3 C22 125.3(3) . . ?
C5 N3 C22 128.1(3) . . ?
C13 N4 C6 104.9(3) . . ?
C17 S1 C14 92.65(17) . . ?
C18 S2 C21 93.2(2) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.074
####################################################################### 
# 
# 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_10CHCl3
_database_code_depnum_ccdc_archive 'CCDC 1018242'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H21 Cl3 N4 S2'
_chemical_formula_sum            'C26 H21 Cl3 N4 S2'
_chemical_formula_weight         559.94

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   9.3385(13)
_cell_length_b                   12.1614(18)
_cell_length_c                   12.8481(19)
_cell_angle_alpha                71.990(3)
_cell_angle_beta                 85.936(3)
_cell_angle_gamma                71.519(3)
_cell_volume                     1315.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4612
_cell_measurement_theta_min      2.305
_cell_measurement_theta_max      22.863

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9391
_exptl_absorpt_correction_T_max  0.9489
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7410
_diffrn_reflns_av_R_equivalents  0.0163
_diffrn_reflns_av_sigmaI/netI    0.0366
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4612
_reflns_number_gt                2340
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0719P)²+0.6989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4612
_refine_ls_number_parameters     357
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1232
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.1876
_refine_ls_wR_factor_gt          0.1652
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7151(5) 0.4353(4) 0.5859(4) 0.1046(14) Uani 1 1 d U . .
H1 H 0.6689 0.3746 0.6050 0.126 Uiso 1 1 calc R . .
C2 C 0.6856(5) 0.5170(5) 0.4815(4) 0.1072(14) Uani 1 1 d . . .
H2 H 0.6225 0.5107 0.4322 0.129 Uiso 1 1 calc R . .
C3 C 0.7529(5) 0.6084(4) 0.4526(4) 0.0976(13) Uani 1 1 d . . .
H3 H 0.7327 0.6661 0.3838 0.117 Uiso 1 1 calc R . .
C4 C 0.8505(4) 0.6137(4) 0.5265(3) 0.0816(11) Uani 1 1 d . . .
C5 C 0.9341(5) 0.6993(3) 0.5083(3) 0.0810(11) Uani 1 1 d . . .
C6 C 1.0310(5) 0.6950(4) 0.5864(3) 0.0835(11) Uani 1 1 d . . .
C7 C 1.0525(5) 0.6072(4) 0.6922(3) 0.0850(11) Uani 1 1 d . . .
C8 C 1.1454(6) 0.6026(4) 0.7732(3) 0.1073(15) Uani 1 1 d . . .
H8 H 1.1986 0.6583 0.7600 0.129 Uiso 1 1 calc R . .
C9 C 1.1598(6) 0.5155(5) 0.8737(4) 0.1166(16) Uani 1 1 d . . .
H9 H 1.2211 0.5112 0.9298 0.140 Uiso 1 1 calc R . .
C10 C 1.0779(6) 0.4339(5) 0.8877(4) 0.1139(16) Uani 1 1 d . . .
H10 H 1.0890 0.3735 0.9547 0.137 Uiso 1 1 calc R . .
C11 C 0.9733(5) 0.5227(3) 0.7157(3) 0.0790(10) Uani 1 1 d . . .
C12 C 0.8732(4) 0.5248(4) 0.6326(3) 0.0829(11) Uani 1 1 d . . .
C13 C 1.0443(5) 0.8416(4) 0.4468(3) 0.0854(11) Uani 1 1 d . . .
C14 C 1.0887(5) 0.9439(4) 0.3765(3) 0.0905(12) Uani 1 1 d . . .
C15 C 1.0321(6) 1.0298(4) 0.2796(4) 0.1133(16) Uani 1 1 d . . .
H15 H 0.9487 1.0331 0.2420 0.136 Uiso 1 1 calc R . .
C16 C 1.1146(7) 1.1136(4) 0.2428(4) 0.1162(17) Uani 1 1 d . . .
H16 H 1.0903 1.1775 0.1779 0.139 Uiso 1 1 calc R . .
C17 C 1.2312(6) 1.0931(4) 0.3094(4) 0.0966(13) Uani 1 1 d . . .
C18 C 1.3324(7) 1.1650(5) 0.2956(5) 0.1034(17) Uani 1 1 d U . .
C19 C 1.421(3) 1.1656(17) 0.3667(16) 0.139(8) Uani 0.742(6) 1 d P . .
H19 H 1.4357 1.1130 0.4380 0.167 Uiso 0.742(6) 1 d PR . .
C19' C 1.313(6) 1.282(4) 0.195(5) 0.139(8) Uani 0.258(6) 1 d PU . .
H19' H 1.2420 1.3205 0.1370 0.167 Uiso 0.258(6) 1 calc PR . .
C20 C 1.5184(6) 1.2455(5) 0.3354(5) 0.1315(19) Uani 1 1 d D . .
H20 H 1.5962 1.2551 0.3696 0.158 Uiso 1 1 d R . .
C21 C 1.4675(7) 1.3119(6) 0.2268(5) 0.157(2) Uani 1 1 d D . .
H21 H 1.5046 1.3746 0.1871 0.188 Uiso 1 1 d R . .
C22 C 0.8798(5) 0.8239(4) 0.3032(4) 0.1048(13) Uani 1 1 d U . .
H22A H 0.9423 0.8613 0.2496 0.126 Uiso 1 1 calc R . .
H22B H 0.8811 0.7494 0.2898 0.126 Uiso 1 1 calc R . .
C23 C 0.7262(7) 0.9058(5) 0.2907(5) 0.148(2) Uani 1 1 d . . .
H23A H 0.7236 0.9775 0.3099 0.177 Uiso 1 1 calc R . .
H23B H 0.6620 0.8658 0.3402 0.177 Uiso 1 1 calc R . .
C24 C 0.6635(9) 0.9454(9) 0.1696(7) 0.221(4) Uani 1 1 d DU . .
H24A H 0.5549 0.9785 0.1735 0.265 Uiso 1 1 calc R . .
H24B H 0.6984 1.0137 0.1302 0.265 Uiso 1 1 calc R . .
C25 C 0.6864(14) 0.8702(11) 0.0952(12) 0.350(9) Uani 1 1 d DU . .
H25A H 0.7895 0.8514 0.0729 0.525 Uiso 1 1 calc R . .
H25B H 0.6204 0.9143 0.0318 0.525 Uiso 1 1 calc R . .
H25C H 0.6643 0.7961 0.1325 0.525 Uiso 1 1 calc R . .
C26 C 0.2429(6) 0.7238(5) 0.1019(4) 0.1227(17) Uani 1 1 d . . .
H26 H 0.1957 0.6718 0.1577 0.147 Uiso 1 1 d R . .
Cl1 Cl 0.2508(11) 0.8353(8) 0.1526(9) 0.158(3) Uani 0.523(12) 1 d P . .
Cl2 Cl 0.1720(16) 0.7695(9) -0.0263(4) 0.208(5) Uani 0.523(12) 1 d P . .
Cl3 Cl 0.4471(9) 0.6392(4) 0.1021(10) 0.215(5) Uani 0.523(12) 1 d P . .
Cl1' Cl 0.0843(7) 0.8329(8) 0.0164(8) 0.189(4) Uani 0.477(12) 1 d P . .
Cl2' Cl 0.3584(14) 0.6402(8) 0.0338(8) 0.230(4) Uani 0.477(12) 1 d P . .
Cl3' Cl 0.316(2) 0.8028(14) 0.1505(10) 0.233(6) Uani 0.477(12) 1 d P . .
N1 N 0.8039(4) 0.4372(3) 0.6602(3) 0.0915(10) Uani 1 1 d U . .
N2 N 0.9867(4) 0.4358(3) 0.8138(3) 0.0936(10) Uani 1 1 d . . .
N3 N 0.9446(4) 0.7939(3) 0.4177(3) 0.0904(10) Uani 1 1 d U . .
N4 N 1.0999(4) 0.7835(3) 0.5475(3) 0.0923(10) Uani 1 1 d . . .
S1 S 1.24277(14) 0.96830(11) 0.42105(9) 0.1030(5) Uani 1 1 d . . .
S2 S 1.3441(5) 1.2711(5) 0.1774(4) 0.1545(18) Uani 0.742(6) 1 d P . .
S1' S 1.449(2) 1.1415(13) 0.4000(12) 0.113(3) Uani 0.258(6) 1 d P . .


_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
C1 N1 1.319(5) . ?
C1 C2 1.384(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.387(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.434(5) . ?
C4 C5 1.445(5) . ?
C5 C6 1.376(5) . ?
C5 N3 1.384(5) . ?
C6 N4 1.372(5) . ?
C6 C7 1.426(5) . ?
C7 C8 1.378(6) . ?
C7 C11 1.398(5) . ?
C8 C9 1.377(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.398(6) . ?
C9 H9 0.9300 . ?
C10 N2 1.310(5) . ?
C10 H10 0.9300 . ?
C11 N2 1.355(5) . ?
C11 C12 1.457(5) . ?
C12 N1 1.360(5) . ?
C13 N4 1.319(5) . ?
C13 N3 1.367(5) . ?
C13 C14 1.455(5) . ?
C14 C15 1.364(6) . ?
C14 S1 1.726(4) . ?
C15 C16 1.415(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.345(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.446(7) . ?
C17 S1 1.716(4) . ?
C18 C19 1.28(2) . ?
C18 C19' 1.57(5) . ?
C18 S2 1.684(7) . ?
C18 S1' 1.685(18) . ?
C19 C20 1.49(2) . ?
C19 H19 0.9300 . ?
C19' C21 1.70(6) . ?
C19' H19' 0.9300 . ?
C20 C21 1.407(6) . ?
C20 S1' 1.582(12) . ?
C20 H20 0.9300 . ?
C21 S2 1.624(9) . ?
C21 H21 0.9300 . ?
C22 C23 1.450(6) . ?
C22 N3 1.522(5) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.575(9) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.477(8) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 Cl3' 1.620(12) . ?
C26 Cl2' 1.638(8) . ?
C26 Cl2 1.677(7) . ?
C26 Cl1 1.699(9) . ?
C26 Cl1' 1.801(8) . ?
C26 Cl3 1.858(9) . ?
C26 H26 0.9800 . ?
S1' H19 0.5363 . ?

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
N1 C1 C2 124.8(4) . . ?
N1 C1 H1 117.6 . . ?
C2 C1 H1 117.6 . . ?
C1 C2 C3 118.0(5) . . ?
C1 C2 H2 121.0 . . ?
C3 C2 H2 121.0 . . ?
C2 C3 C4 120.0(4) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 117.6(4) . . ?
C3 C4 C5 127.1(4) . . ?
C12 C4 C5 115.3(4) . . ?
C6 C5 N3 105.3(3) . . ?
C6 C5 C4 122.6(4) . . ?
N3 C5 C4 132.0(4) . . ?
N4 C6 C5 111.1(4) . . ?
N4 C6 C7 126.9(4) . . ?
C5 C6 C7 122.0(4) . . ?
C8 C7 C11 118.2(4) . . ?
C8 C7 C6 123.5(4) . . ?
C11 C7 C6 118.3(4) . . ?
C9 C8 C7 120.1(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 116.9(5) . . ?
C8 C9 H9 121.5 . . ?
C10 C9 H9 121.5 . . ?
N2 C10 C9 125.1(4) . . ?
N2 C10 H10 117.4 . . ?
C9 C10 H10 117.4 . . ?
N2 C11 C7 122.5(4) . . ?
N2 C11 C12 117.4(3) . . ?
C7 C11 C12 120.0(4) . . ?
N1 C12 C4 121.6(4) . . ?
N1 C12 C11 116.6(4) . . ?
C4 C12 C11 121.7(4) . . ?
N4 C13 N3 112.6(3) . . ?
N4 C13 C14 122.1(4) . . ?
N3 C13 C14 125.2(4) . . ?
C15 C14 C13 133.3(4) . . ?
C15 C14 S1 110.2(3) . . ?
C13 C14 S1 116.5(3) . . ?
C14 C15 C16 112.4(5) . . ?
C14 C15 H15 123.8 . . ?
C16 C15 H15 123.8 . . ?
C17 C16 C15 114.4(4) . . ?
C17 C16 H16 122.8 . . ?
C15 C16 H16 122.8 . . ?
C16 C17 C18 127.2(5) . . ?
C16 C17 S1 110.2(3) . . ?
C18 C17 S1 122.6(4) . . ?
C19 C18 C17 128.6(9) . . ?
C19 C18 C19' 109(3) . . ?
C17 C18 C19' 121(2) . . ?
C19 C18 S2 108.2(8) . . ?
C17 C18 S2 123.1(5) . . ?
C19' C18 S2 12.2(19) . . ?
C19 C18 S1' 9.7(10) . . ?
C17 C18 S1' 119.8(4) . . ?
C19' C18 S1' 118(2) . . ?
S2 C18 S1' 117.0(5) . . ?
C18 C19 C20 120.3(12) . . ?
C18 C19 H19 123.9 . . ?
C20 C19 H19 115.6 . . ?
C18 C19' C21 95(3) . . ?
C18 C19' H19' 132.4 . . ?
C21 C19' H19' 132.4 . . ?
C21 C20 C19 101.1(9) . . ?
C21 C20 S1' 118.3(8) . . ?
C19 C20 S1' 17.5(11) . . ?
C21 C20 H20 123.6 . . ?
C19 C20 H20 135.3 . . ?
S1' C20 H20 117.9 . . ?
C20 C21 S2 116.1(4) . . ?
C20 C21 C19' 111.2(17) . . ?
S2 C21 C19' 12.3(18) . . ?
C20 C21 H21 120.4 . . ?
S2 C21 H21 123.5 . . ?
C19' C21 H21 127.2 . . ?
C23 C22 N3 111.2(4) . . ?
C23 C22 H22A 109.4 . . ?
N3 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
N3 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 111.2(5) . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23B 109.4 . . ?
C24 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C25 C24 C23 128.2(9) . . ?
C25 C24 H24A 105.3 . . ?
C23 C24 H24A 105.3 . . ?
C25 C24 H24B 105.3 . . ?
C23 C24 H24B 105.3 . . ?
H24A C24 H24B 106.0 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
Cl3' C26 Cl2' 115.3(6) . . ?
Cl3' C26 Cl2 124.0(6) . . ?
Cl2' C26 Cl2 72.0(4) . . ?
Cl3' C26 Cl1 21.1(8) . . ?
Cl2' C26 Cl1 134.7(5) . . ?
Cl2 C26 Cl1 116.2(6) . . ?
Cl3' C26 Cl1' 105.3(6) . . ?
Cl2' C26 Cl1' 111.1(5) . . ?
Cl2 C26 Cl1' 39.1(3) . . ?
Cl1 C26 Cl1' 88.1(6) . . ?
Cl3' C26 Cl3 79.3(6) . . ?
Cl2' C26 Cl3 41.1(3) . . ?
Cl2 C26 Cl3 108.5(4) . . ?
Cl1 C26 Cl3 100.5(5) . . ?
Cl1' C26 Cl3 144.0(4) . . ?
Cl3' C26 H26 113.1 . . ?
Cl2' C26 H26 108.4 . . ?
Cl2 C26 H26 116.1 . . ?
Cl1 C26 H26 106.4 . . ?
Cl1' C26 H26 102.9 . . ?
Cl3 C26 H26 107.9 . . ?
C1 N1 C12 118.0(4) . . ?
C10 N2 C11 117.1(4) . . ?
C13 N3 C5 106.3(3) . . ?
C13 N3 C22 126.6(3) . . ?
C5 N3 C22 126.4(4) . . ?
C13 N4 C6 104.7(3) . . ?
C17 S1 C14 92.8(2) . . ?
C21 S2 C18 94.0(4) . . ?
C20 S1' C18 94.4(6) . . ?
C20 S1' H19 150.2 . . ?
C18 S1' H19 112.5 . . ?

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
N1 C1 C2 C3 -0.5(7) . . . . ?
C1 C2 C3 C4 2.0(7) . . . . ?
C2 C3 C4 C12 -2.1(6) . . . . ?
C2 C3 C4 C5 177.4(4) . . . . ?
C3 C4 C5 C6 -178.4(4) . . . . ?
C12 C4 C5 C6 1.1(6) . . . . ?
C3 C4 C5 N3 -1.5(7) . . . . ?
C12 C4 C5 N3 178.1(4) . . . . ?
N3 C5 C6 N4 0.3(4) . . . . ?
C4 C5 C6 N4 177.9(3) . . . . ?
N3 C5 C6 C7 -179.4(4) . . . . ?
C4 C5 C6 C7 -1.8(6) . . . . ?
N4 C6 C7 C8 2.2(7) . . . . ?
C5 C6 C7 C8 -178.2(4) . . . . ?
N4 C6 C7 C11 -178.9(4) . . . . ?
C5 C6 C7 C11 0.8(6) . . . . ?
C11 C7 C8 C9 0.7(7) . . . . ?
C6 C7 C8 C9 179.6(4) . . . . ?
C7 C8 C9 C10 0.6(8) . . . . ?
C8 C9 C10 N2 -1.6(8) . . . . ?
C8 C7 C11 N2 -1.2(6) . . . . ?
C6 C7 C11 N2 179.8(4) . . . . ?
C8 C7 C11 C12 179.7(4) . . . . ?
C6 C7 C11 C12 0.7(6) . . . . ?
C3 C4 C12 N1 0.9(6) . . . . ?
C5 C4 C12 N1 -178.7(3) . . . . ?
C3 C4 C12 C11 180.0(4) . . . . ?
C5 C4 C12 C11 0.3(5) . . . . ?
N2 C11 C12 N1 -1.3(5) . . . . ?
C7 C11 C12 N1 177.8(4) . . . . ?
N2 C11 C12 C4 179.6(3) . . . . ?
C7 C11 C12 C4 -1.3(6) . . . . ?
N4 C13 C14 C15 -167.2(5) . . . . ?
N3 C13 C14 C15 13.7(8) . . . . ?
N4 C13 C14 S1 11.6(5) . . . . ?
N3 C13 C14 S1 -167.5(3) . . . . ?
C13 C14 C15 C16 179.2(4) . . . . ?
S1 C14 C15 C16 0.3(5) . . . . ?
C14 C15 C16 C17 -0.2(7) . . . . ?
C15 C16 C17 C18 -177.9(5) . . . . ?
C15 C16 C17 S1 0.0(6) . . . . ?
C16 C17 C18 C19 162.8(15) . . . . ?
S1 C17 C18 C19 -14.9(17) . . . . ?
C16 C17 C18 C19' 0(2) . . . . ?
S1 C17 C18 C19' -177(2) . . . . ?
C16 C17 C18 S2 -13.9(8) . . . . ?
S1 C17 C18 S2 168.4(4) . . . . ?
C16 C17 C18 S1' 167.7(9) . . . . ?
S1 C17 C18 S1' -10.0(10) . . . . ?
C17 C18 C19 C20 179.1(9) . . . . ?
C19' C18 C19 C20 -17(3) . . . . ?
S2 C18 C19 C20 -4(2) . . . . ?
S1' C18 C19 C20 153(12) . . . . ?
C19 C18 C19' C21 17(3) . . . . ?
C17 C18 C19' C21 -177.1(9) . . . . ?
S2 C18 C19' C21 -72(11) . . . . ?
S1' C18 C19' C21 15(3) . . . . ?
C18 C19 C20 C21 6(2) . . . . ?
C18 C19 C20 S1' -164(7) . . . . ?
C19 C20 C21 S2 -5.1(12) . . . . ?
S1' C20 C21 S2 -1.7(11) . . . . ?
C19 C20 C21 C19' 7(2) . . . . ?
S1' C20 C21 C19' 11(2) . . . . ?
C18 C19' C21 C20 -15(3) . . . . ?
C18 C19' C21 S2 101(9) . . . . ?
N3 C22 C23 C24 175.4(6) . . . . ?
C22 C23 C24 C25 39.4(14) . . . . ?
C2 C1 N1 C12 -0.7(7) . . . . ?
C4 C12 N1 C1 0.5(6) . . . . ?
C11 C12 N1 C1 -178.6(4) . . . . ?
C9 C10 N2 C11 1.2(7) . . . . ?
C7 C11 N2 C10 0.3(6) . . . . ?
C12 C11 N2 C10 179.4(4) . . . . ?
N4 C13 N3 C5 1.3(5) . . . . ?
C14 C13 N3 C5 -179.5(4) . . . . ?
N4 C13 N3 C22 -169.1(4) . . . . ?
C14 C13 N3 C22 10.1(7) . . . . ?
C6 C5 N3 C13 -0.9(4) . . . . ?
C4 C5 N3 C13 -178.2(4) . . . . ?
C6 C5 N3 C22 169.5(4) . . . . ?
C4 C5 N3 C22 -7.8(7) . . . . ?
C23 C22 N3 C13 -102.5(5) . . . . ?
C23 C22 N3 C5 88.9(5) . . . . ?
N3 C13 N4 C6 -1.1(5) . . . . ?
C14 C13 N4 C6 179.7(4) . . . . ?
C5 C6 N4 C13 0.4(5) . . . . ?
C7 C6 N4 C13 -179.9(4) . . . . ?
C16 C17 S1 C14 0.1(4) . . . . ?
C18 C17 S1 C14 178.1(4) . . . . ?
C15 C14 S1 C17 -0.2(4) . . . . ?
C13 C14 S1 C17 -179.3(3) . . . . ?
C20 C21 S2 C18 3.2(6) . . . . ?
C19' C21 S2 C18 -66(8) . . . . ?
C19 C18 S2 C21 0.4(13) . . . . ?
C17 C18 S2 C21 177.7(5) . . . . ?
C19' C18 S2 C21 95(12) . . . . ?
S1' C18 S2 C21 -3.9(9) . . . . ?
C21 C20 S1' C18 -0.9(13) . . . . ?
C19 C20 S1' C18 10(5) . . . . ?
C19 C18 S1' C20 -22(10) . . . . ?
C17 C18 S1' C20 -178.3(6) . . . . ?
C19' C18 S1' C20 -11(2) . . . . ?
S2 C18 S1' C20 3.2(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.415
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_11
_database_code_depnum_ccdc_archive 'CCDC 1018243'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 Cl3 N4 O S2'
_chemical_formula_sum            'C27 H21 Cl3 N4 O S2'
_chemical_formula_weight         587.95

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   5.2878(14)
_cell_length_b                   33.975(9)
_cell_length_c                   14.927(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.610(5)
_cell_angle_gamma                90.00
_cell_volume                     2658.1(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    4682
_cell_measurement_theta_min      2.265
_cell_measurement_theta_max      20.356

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    0.532
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9488
_exptl_absorpt_correction_T_max  0.9488
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14843
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_av_sigmaI/netI    0.0719
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.50
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4682
_reflns_number_gt                2511
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0630P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4682
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0535
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.2745(8) 0.28390(11) 0.8700(3) 0.0699(12) Uani 1 1 d . . .
H1 H 1.3890 0.2633 0.8830 0.084 Uiso 1 1 calc R . .
C2 C 1.0635(9) 0.27782(11) 0.8050(3) 0.0685(12) Uani 1 1 d . . .
H2 H 1.0368 0.2535 0.7766 0.082 Uiso 1 1 calc R . .
C3 C 0.8955(8) 0.30828(10) 0.7836(2) 0.0568(10) Uani 1 1 d . . .
H3 H 0.7549 0.3048 0.7398 0.068 Uiso 1 1 calc R . .
C4 C 0.9362(7) 0.34476(10) 0.8279(2) 0.0460(9) Uani 1 1 d . . .
C5 C 0.7883(7) 0.37982(10) 0.8104(2) 0.0432(9) Uani 1 1 d . . .
C6 C 0.8491(7) 0.41495(10) 0.8551(2) 0.0438(9) Uani 1 1 d . . .
C7 C 1.0670(7) 0.41820(10) 0.9231(2) 0.0442(9) Uani 1 1 d . . .
C8 C 1.1314(7) 0.45300(11) 0.9698(2) 0.0542(10) Uani 1 1 d . . .
H8 H 1.0314 0.4754 0.9585 0.065 Uiso 1 1 calc R . .
C9 C 1.3444(8) 0.45364(11) 1.0327(2) 0.0580(11) Uani 1 1 d . . .
H9 H 1.3934 0.4765 1.0645 0.070 Uiso 1 1 calc R . .
C10 C 1.4862(8) 0.41911(12) 1.0478(2) 0.0630(12) Uani 1 1 d . . .
H10 H 1.6306 0.4199 1.0907 0.076 Uiso 1 1 calc R . .
C11 C 1.2202(7) 0.38465(10) 0.9427(2) 0.0451(9) Uani 1 1 d . . .
C12 C 1.1568(7) 0.34772(10) 0.8941(2) 0.0479(9) Uani 1 1 d . . .
C13 C 0.5178(7) 0.42763(11) 0.7625(2) 0.0472(9) Uani 1 1 d . . .
C14 C 0.4082(7) 0.36030(10) 0.6937(2) 0.0532(10) Uani 1 1 d . . .
H14A H 0.2337 0.3698 0.6869 0.064 Uiso 1 1 calc R . .
H14B H 0.4124 0.3353 0.7252 0.064 Uiso 1 1 calc R . .
C15 C 0.4826(8) 0.35350(11) 0.6014(2) 0.0620(11) Uani 1 1 d . . .
H15A H 0.6546 0.3430 0.6068 0.074 Uiso 1 1 calc R . .
H15B H 0.4794 0.3782 0.5688 0.074 Uiso 1 1 calc R . .
C16 C 0.2944(10) 0.32413(13) 0.5493(3) 0.0906(16) Uani 1 1 d . . .
H16A H 0.3158 0.2986 0.5785 0.109 Uiso 1 1 calc R . .
H16B H 0.1215 0.3329 0.5531 0.109 Uiso 1 1 calc R . .
C17 C 0.3271(12) 0.31960(15) 0.4533(3) 0.123(2) Uani 1 1 d . . .
H17A H 0.2995 0.3445 0.4232 0.184 Uiso 1 1 calc R . .
H17B H 0.2061 0.3008 0.4255 0.184 Uiso 1 1 calc R . .
H17C H 0.4970 0.3106 0.4488 0.184 Uiso 1 1 calc R . .
C18 C 0.3057(7) 0.44984(10) 0.7143(2) 0.0480(9) Uani 1 1 d . . .
C19 C 0.1525(8) 0.44339(12) 0.6345(2) 0.0623(11) Uani 1 1 d . . .
H19 H 0.1686 0.4217 0.5975 0.075 Uiso 1 1 calc R . .
C20 C -0.0316(8) 0.47296(12) 0.6143(2) 0.0601(11) Uani 1 1 d . . .
H20 H -0.1513 0.4727 0.5627 0.072 Uiso 1 1 calc R . .
C21 C -0.0183(7) 0.50184(10) 0.6771(2) 0.0491(10) Uani 1 1 d . . .
C22 C -0.1850(7) 0.53629(11) 0.6809(2) 0.0479(9) Uani 1 1 d . . .
C23 C -0.1852(7) 0.56340(11) 0.7464(3) 0.0592(11) Uani 1 1 d . . .
H23 H -0.0660 0.5637 0.7981 0.071 Uiso 1 1 calc R . .
C24 C -0.3813(8) 0.59120(12) 0.7296(3) 0.0660(12) Uani 1 1 d . . .
H24 H -0.4050 0.6120 0.7682 0.079 Uiso 1 1 calc R . .
C25 C -0.5340(7) 0.58421(11) 0.6497(2) 0.0566(10) Uani 1 1 d . . .
C26 C -0.7550(8) 0.60637(12) 0.6126(3) 0.0680(12) Uani 1 1 d . . .
H26 H -0.8038 0.6274 0.6464 0.082 Uiso 1 1 calc R . .
C27 C 0.2920(9) 0.69181(12) 0.9008(3) 0.0770(13) Uani 1 1 d . . .
H27 H 0.4113 0.6786 0.9471 0.092 Uiso 1 1 calc R . .
Cl1 Cl 0.0649(3) 0.65856(5) 0.85453(13) 0.1378(7) Uani 1 1 d . . .
Cl2 Cl 0.1465(3) 0.73078(4) 0.94998(10) 0.1271(6) Uani 1 1 d . . .
Cl3 Cl 0.4576(3) 0.70956(6) 0.81645(13) 0.1576(8) Uani 1 1 d . . .
N1 N 1.3207(6) 0.31745(9) 0.9142(2) 0.0578(9) Uani 1 1 d . . .
N2 N 1.4312(6) 0.38519(9) 1.00581(19) 0.0545(8) Uani 1 1 d . . .
N3 N 0.5706(5) 0.38845(8) 0.74995(17) 0.0457(7) Uani 1 1 d . . .
N4 N 0.6824(5) 0.44437(8) 0.82575(18) 0.0475(8) Uani 1 1 d . . .
O1 O -0.8820(6) 0.59981(8) 0.5409(2) 0.0834(10) Uani 1 1 d . . .
S1 S 0.22645(18) 0.49322(3) 0.76325(6) 0.0515(3) Uani 1 1 d . . .
S2 S -0.4321(2) 0.54381(3) 0.59545(6) 0.0586(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
C1 N1 1.324(5) . ?
C1 C2 1.393(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.373(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.408(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.429(5) . ?
C4 C5 1.430(4) . ?
C5 C6 1.384(4) . ?
C5 N3 1.397(4) . ?
C6 N4 1.366(4) . ?
C6 C7 1.436(4) . ?
C7 C8 1.392(4) . ?
C7 C11 1.406(4) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.395(5) . ?
C9 H9 0.9300 . ?
C10 N2 1.326(4) . ?
C10 H10 0.9300 . ?
C11 N2 1.362(4) . ?
C11 C12 1.466(5) . ?
C12 N1 1.353(4) . ?
C13 N4 1.325(4) . ?
C13 N3 1.378(4) . ?
C13 C18 1.460(5) . ?
C14 N3 1.472(4) . ?
C14 C15 1.499(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.545(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.474(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.367(4) . ?
C18 S1 1.721(4) . ?
C19 C20 1.404(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.352(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.471(5) . ?
C21 S1 1.724(3) . ?
C22 C23 1.343(5) . ?
C22 S2 1.720(3) . ?
C23 C24 1.400(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.369(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.438(5) . ?
C25 S2 1.716(4) . ?
C26 O1 1.206(4) . ?
C26 H26 0.9300 . ?
C27 Cl1 1.725(4) . ?
C27 Cl3 1.735(5) . ?
C27 Cl2 1.741(5) . ?
C27 H27 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 123.6(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 118.9(4) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 120.0(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 116.5(3) . . ?
C3 C4 C5 127.0(3) . . ?
C12 C4 C5 116.4(3) . . ?
C6 C5 N3 104.4(3) . . ?
C6 C5 C4 123.0(3) . . ?
N3 C5 C4 132.6(3) . . ?
N4 C6 C5 112.2(3) . . ?
N4 C6 C7 126.4(3) . . ?
C5 C6 C7 121.4(3) . . ?
C8 C7 C11 119.2(3) . . ?
C8 C7 C6 122.7(3) . . ?
C11 C7 C6 118.1(3) . . ?
C9 C8 C7 118.8(3) . . ?
C9 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
C8 C9 C10 118.3(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 125.1(3) . . ?
N2 C10 H10 117.4 . . ?
C9 C10 H10 117.4 . . ?
N2 C11 C7 122.0(3) . . ?
N2 C11 C12 117.8(3) . . ?
C7 C11 C12 120.2(3) . . ?
N1 C12 C4 122.7(3) . . ?
N1 C12 C11 116.3(3) . . ?
C4 C12 C11 121.0(3) . . ?
N4 C13 N3 112.7(3) . . ?
N4 C13 C18 121.2(3) . . ?
N3 C13 C18 126.1(3) . . ?
N3 C14 C15 114.8(3) . . ?
N3 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
N3 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.5 . . ?
C14 C15 C16 109.4(4) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 114.0(4) . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C15 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C13 132.4(3) . . ?
C19 C18 S1 111.0(3) . . ?
C13 C18 S1 116.6(2) . . ?
C18 C19 C20 112.7(3) . . ?
C18 C19 H19 123.6 . . ?
C20 C19 H19 123.6 . . ?
C21 C20 C19 113.6(3) . . ?
C21 C20 H20 123.2 . . ?
C19 C20 H20 123.2 . . ?
C20 C21 C22 128.9(3) . . ?
C20 C21 S1 111.0(3) . . ?
C22 C21 S1 120.1(3) . . ?
C23 C22 C21 129.2(3) . . ?
C23 C22 S2 111.3(3) . . ?
C21 C22 S2 119.3(3) . . ?
C22 C23 C24 113.9(3) . . ?
C22 C23 H23 123.1 . . ?
C24 C23 H23 123.1 . . ?
C25 C24 C23 112.1(4) . . ?
C25 C24 H24 124.0 . . ?
C23 C24 H24 124.0 . . ?
C24 C25 C26 126.9(4) . . ?
C24 C25 S2 111.4(3) . . ?
C26 C25 S2 121.8(3) . . ?
O1 C26 C25 125.0(4) . . ?
O1 C26 H26 117.5 . . ?
C25 C26 H26 117.5 . . ?
Cl1 C27 Cl3 109.2(3) . . ?
Cl1 C27 Cl2 110.1(3) . . ?
Cl3 C27 Cl2 109.6(2) . . ?
Cl1 C27 H27 109.3 . . ?
Cl3 C27 H27 109.3 . . ?
Cl2 C27 H27 109.3 . . ?
C1 N1 C12 118.3(3) . . ?
C10 N2 C11 116.6(3) . . ?
C13 N3 C5 106.2(3) . . ?
C13 N3 C14 126.3(3) . . ?
C5 N3 C14 126.9(3) . . ?
C13 N4 C6 104.4(3) . . ?
C18 S1 C21 91.71(17) . . ?
C25 S2 C22 91.37(18) . . ?

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
N1 C1 C2 C3 1.4(7) . . . . ?
C1 C2 C3 C4 -0.8(6) . . . . ?
C2 C3 C4 C12 0.1(6) . . . . ?
C2 C3 C4 C5 176.4(4) . . . . ?
C3 C4 C5 C6 -177.3(4) . . . . ?
C12 C4 C5 C6 -0.9(5) . . . . ?
C3 C4 C5 N3 1.4(7) . . . . ?
C12 C4 C5 N3 177.7(4) . . . . ?
N3 C5 C6 N4 0.0(4) . . . . ?
C4 C5 C6 N4 179.0(3) . . . . ?
N3 C5 C6 C7 -179.3(3) . . . . ?
C4 C5 C6 C7 -0.3(6) . . . . ?
N4 C6 C7 C8 1.5(6) . . . . ?
C5 C6 C7 C8 -179.3(4) . . . . ?
N4 C6 C7 C11 -178.5(3) . . . . ?
C5 C6 C7 C11 0.7(5) . . . . ?
C11 C7 C8 C9 0.9(6) . . . . ?
C6 C7 C8 C9 -179.1(4) . . . . ?
C7 C8 C9 C10 -0.7(6) . . . . ?
C8 C9 C10 N2 0.0(6) . . . . ?
C8 C7 C11 N2 -0.4(6) . . . . ?
C6 C7 C11 N2 179.6(3) . . . . ?
C8 C7 C11 C12 -179.7(3) . . . . ?
C6 C7 C11 C12 0.3(5) . . . . ?
C3 C4 C12 N1 0.0(5) . . . . ?
C5 C4 C12 N1 -176.7(3) . . . . ?
C3 C4 C12 C11 178.6(3) . . . . ?
C5 C4 C12 C11 1.9(5) . . . . ?
N2 C11 C12 N1 -2.3(5) . . . . ?
C7 C11 C12 N1 177.0(3) . . . . ?
N2 C11 C12 C4 179.1(3) . . . . ?
C7 C11 C12 C4 -1.6(5) . . . . ?
N3 C14 C15 C16 -178.9(3) . . . . ?
C14 C15 C16 C17 171.7(4) . . . . ?
N4 C13 C18 C19 161.3(4) . . . . ?
N3 C13 C18 C19 -19.4(7) . . . . ?
N4 C13 C18 S1 -17.6(5) . . . . ?
N3 C13 C18 S1 161.7(3) . . . . ?
C13 C18 C19 C20 179.6(4) . . . . ?
S1 C18 C19 C20 -1.4(5) . . . . ?
C18 C19 C20 C21 0.6(5) . . . . ?
C19 C20 C21 C22 -177.0(4) . . . . ?
C19 C20 C21 S1 0.4(5) . . . . ?
C20 C21 C22 C23 174.3(4) . . . . ?
S1 C21 C22 C23 -2.9(6) . . . . ?
C20 C21 C22 S2 -1.4(6) . . . . ?
S1 C21 C22 S2 -178.7(2) . . . . ?
C21 C22 C23 C24 -176.7(4) . . . . ?
S2 C22 C23 C24 -0.7(5) . . . . ?
C22 C23 C24 C25 0.9(5) . . . . ?
C23 C24 C25 C26 178.7(4) . . . . ?
C23 C24 C25 S2 -0.7(5) . . . . ?
C24 C25 C26 O1 178.3(4) . . . . ?
S2 C25 C26 O1 -2.3(7) . . . . ?
C2 C1 N1 C12 -1.2(7) . . . . ?
C4 C12 N1 C1 0.5(6) . . . . ?
C11 C12 N1 C1 -178.1(4) . . . . ?
C9 C10 N2 C11 0.5(6) . . . . ?
C7 C11 N2 C10 -0.3(5) . . . . ?
C12 C11 N2 C10 179.1(3) . . . . ?
N4 C13 N3 C5 -0.3(4) . . . . ?
C18 C13 N3 C5 -179.6(3) . . . . ?
N4 C13 N3 C14 171.7(3) . . . . ?
C18 C13 N3 C14 -7.6(6) . . . . ?
C6 C5 N3 C13 0.2(4) . . . . ?
C4 C5 N3 C13 -178.6(4) . . . . ?
C6 C5 N3 C14 -171.8(3) . . . . ?
C4 C5 N3 C14 9.4(6) . . . . ?
C15 C14 N3 C13 98.4(4) . . . . ?
C15 C14 N3 C5 -91.1(4) . . . . ?
N3 C13 N4 C6 0.3(4) . . . . ?
C18 C13 N4 C6 179.7(3) . . . . ?
C5 C6 N4 C13 -0.2(4) . . . . ?
C7 C6 N4 C13 179.1(4) . . . . ?
C19 C18 S1 C21 1.4(3) . . . . ?
C13 C18 S1 C21 -179.5(3) . . . . ?
C20 C21 S1 C18 -1.0(3) . . . . ?
C22 C21 S1 C18 176.6(3) . . . . ?
C24 C25 S2 C22 0.3(3) . . . . ?
C26 C25 S2 C22 -179.1(4) . . . . ?
C23 C22 S2 C25 0.2(3) . . . . ?
C21 C22 S2 C25 176.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.051
####################################################################### 
# 
# 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_12
_database_code_depnum_ccdc_archive 'CCDC 1018244'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 N4 O2 S'
_chemical_formula_sum            'C26 H20 N4 O2 S'
_chemical_formula_weight         452.52

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   13.7672(19)
_cell_length_b                   8.3667(12)
_cell_length_c                   19.124(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.372(2)
_cell_angle_gamma                90.00
_cell_volume                     2090.5(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    3654
_cell_measurement_theta_min      2.288
_cell_measurement_theta_max      25.826

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             944
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9814
_exptl_absorpt_correction_T_max  0.9814
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11098
_diffrn_reflns_av_R_equivalents  0.1061
_diffrn_reflns_av_sigmaI/netI    0.1015
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         24.99
_reflns_number_total             3654
_reflns_number_gt                2547
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0984P)²+7.8993P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3654
_refine_ls_number_parameters     299
_refine_ls_number_restraints     21
_refine_ls_R_factor_all          0.1260
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2429
_refine_ls_wR_factor_gt          0.2192
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6669(4) 0.1203(6) -0.0456(3) 0.0298(12) Uani 1 1 d . . .
H1 H 0.7233 0.0777 -0.0558 0.036 Uiso 1 1 calc R . .
C2 C 0.5968(4) 0.2085(6) -0.1000(3) 0.0310(12) Uani 1 1 d . . .
H2 H 0.6065 0.2236 -0.1455 0.037 Uiso 1 1 calc R . .
C3 C 0.5143(4) 0.2724(6) -0.0863(3) 0.0263(11) Uani 1 1 d . . .
H3 H 0.4667 0.3307 -0.1226 0.032 Uiso 1 1 calc R . .
C4 C 0.5005(4) 0.2506(5) -0.0170(3) 0.0235(11) Uani 1 1 d . . .
C5 C 0.4190(4) 0.3125(6) 0.0070(3) 0.0237(11) Uani 1 1 d . . .
C6 C 0.4117(4) 0.2797(6) 0.0762(3) 0.0233(11) Uani 1 1 d . . .
C7 C 0.4857(4) 0.1821(6) 0.1285(3) 0.0250(11) Uani 1 1 d . . .
C8 C 0.4778(4) 0.1428(6) 0.1982(3) 0.0274(11) Uani 1 1 d . . .
H8 H 0.4229 0.1783 0.2126 0.033 Uiso 1 1 calc R . .
C9 C 0.5538(4) 0.0503(6) 0.2442(3) 0.0327(12) Uani 1 1 d . . .
H9 H 0.5511 0.0212 0.2905 0.039 Uiso 1 1 calc R . .
C10 C 0.6351(4) 0.0005(6) 0.2206(3) 0.0303(12) Uani 1 1 d . . .
H10 H 0.6866 -0.0598 0.2531 0.036 Uiso 1 1 calc R . .
C11 C 0.5683(4) 0.1223(5) 0.1081(3) 0.0246(11) Uani 1 1 d . . .
C12 C 0.5759(4) 0.1555(6) 0.0349(3) 0.0231(11) Uani 1 1 d . . .
C13 C 0.2851(4) 0.4294(6) 0.0241(3) 0.0251(11) Uani 1 1 d . . .
C14 C 0.1942(4) 0.5300(6) 0.0133(3) 0.0282(11) Uani 1 1 d . . .
C15 C 0.1252(4) 0.5907(6) -0.0491(3) 0.0293(12) Uani 1 1 d . . .
H15 H 0.1280 0.5716 -0.0963 0.035 Uiso 1 1 calc R . .
C16 C 0.0495(4) 0.6848(6) -0.0344(3) 0.0315(12) Uani 1 1 d . . .
H16 H -0.0027 0.7349 -0.0710 0.038 Uiso 1 1 calc R . .
C17 C 0.0602(4) 0.6959(6) 0.0404(3) 0.0313(11) Uani 1 1 d DU . .
C18 C -0.0105(4) 0.7905(6) 0.0755(3) 0.0321(9) Uani 1 1 d DU . .
C19 C -0.0894(5) 0.8677(8) 0.0425(4) 0.0482(15) Uani 1 1 d U . .
H19 H -0.1182 0.8822 -0.0081 0.058 Uiso 1 1 calc R . .
C20 C -0.1246(5) 0.9269(8) 0.0977(4) 0.0501(16) Uani 1 1 d . . .
H20 H -0.1829 0.9890 0.0913 0.060 Uiso 1 1 calc R . .
C21 C -0.0588(4) 0.8780(7) 0.1628(4) 0.0427(9) Uani 1 1 d U . .
C22 C -0.0562(7) 0.9036(11) 0.2369(5) 0.075(2) Uani 1 1 d U . .
H22 H -0.1056 0.9676 0.2466 0.090 Uiso 1 1 calc R . .
C23 C 0.3201(4) 0.5005(6) -0.0961(3) 0.0273(11) Uani 1 1 d . . .
H23A H 0.3862 0.5292 -0.1006 0.033 Uiso 1 1 calc R . .
H23B H 0.2843 0.5989 -0.0932 0.033 Uiso 1 1 calc R . .
C24 C 0.2596(4) 0.4107(6) -0.1648(3) 0.0297(12) Uani 1 1 d . . .
H24A H 0.1911 0.3896 -0.1631 0.036 Uiso 1 1 calc R . .
H24B H 0.2924 0.3089 -0.1669 0.036 Uiso 1 1 calc R . .
C25 C 0.2536(5) 0.5078(7) -0.2329(3) 0.0377(14) Uani 1 1 d . . .
H25A H 0.3225 0.5310 -0.2332 0.045 Uiso 1 1 calc R . .
H25B H 0.2204 0.6089 -0.2303 0.045 Uiso 1 1 calc R . .
C26 C 0.1953(5) 0.4239(8) -0.3050(3) 0.0478(16) Uani 1 1 d . . .
H26A H 0.2298 0.3265 -0.3093 0.072 Uiso 1 1 calc R . .
H26B H 0.1923 0.4926 -0.3458 0.072 Uiso 1 1 calc R . .
H26C H 0.1270 0.3999 -0.3051 0.072 Uiso 1 1 calc R . .
N1 N 0.6573(3) 0.0938(5) 0.0200(2) 0.0282(10) Uani 1 1 d . . .
N2 N 0.6439(3) 0.0331(5) 0.1554(2) 0.0286(10) Uani 1 1 d . . .
N3 N 0.3370(3) 0.4103(5) -0.0267(2) 0.0256(9) Uani 1 1 d . . .
N4 N 0.3275(3) 0.3523(5) 0.0857(2) 0.0263(10) Uani 1 1 d . . .
O1 O 0.0230(3) 0.7740(5) 0.1575(2) 0.0388(8) Uani 1 1 d U . .
O2 O 0.0131(7) 0.8400(14) 0.2898(4) 0.149(4) Uani 1 1 d . . .
S1 S 0.16622(10) 0.58676(16) 0.09116(7) 0.0304(4) 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
C1 N1 1.321(6) . ?
C1 C2 1.386(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.354(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.407(7) . ?
C3 H3 0.9300 . ?
C4 C12 1.431(7) . ?
C4 C5 1.437(7) . ?
C5 N3 1.379(6) . ?
C5 C6 1.387(7) . ?
C6 N4 1.371(6) . ?
C6 C7 1.436(7) . ?
C7 C11 1.405(7) . ?
C7 C8 1.410(7) . ?
C8 C9 1.373(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.396(8) . ?
C9 H9 0.9300 . ?
C10 N2 1.319(7) . ?
C10 H10 0.9300 . ?
C11 N2 1.365(6) . ?
C11 C12 1.463(7) . ?
C12 N1 1.343(6) . ?
C13 N4 1.310(6) . ?
C13 N3 1.384(6) . ?
C13 C14 1.467(7) . ?
C14 C15 1.367(7) . ?
C14 S1 1.719(5) . ?
C15 C16 1.402(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.561(6) . ?
C17 S1 1.736(5) . ?
C18 C19 1.251(8) . ?
C18 O1 1.495(7) . ?
C19 C20 1.386(9) . ?
C19 H19 0.9300 . ?
C20 C21 1.351(9) . ?
C20 H20 0.9300 . ?
C21 C22 1.423(10) . ?
C21 O1 1.451(7) . ?
C22 O2 1.268(11) . ?
C22 H22 0.9300 . ?
C23 N3 1.480(6) . ?
C23 C24 1.515(7) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.515(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.530(8) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 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
N1 C1 C2 123.2(5) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.5(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C12 116.2(4) . . ?
C3 C4 C5 127.2(5) . . ?
C12 C4 C5 116.6(4) . . ?
N3 C5 C6 105.6(4) . . ?
N3 C5 C4 132.2(4) . . ?
C6 C5 C4 122.2(5) . . ?
N4 C6 C5 111.0(4) . . ?
N4 C6 C7 127.1(4) . . ?
C5 C6 C7 121.9(4) . . ?
C11 C7 C8 119.3(5) . . ?
C11 C7 C6 117.9(4) . . ?
C8 C7 C6 122.8(5) . . ?
C9 C8 C7 117.8(5) . . ?
C9 C8 H8 121.1 . . ?
C7 C8 H8 121.1 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
N2 C10 C9 124.4(5) . . ?
N2 C10 H10 117.8 . . ?
C9 C10 H10 117.8 . . ?
N2 C11 C7 121.7(5) . . ?
N2 C11 C12 117.9(4) . . ?
C7 C11 C12 120.4(5) . . ?
N1 C12 C4 122.5(4) . . ?
N1 C12 C11 116.5(4) . . ?
C4 C12 C11 120.9(4) . . ?
N4 C13 N3 113.2(4) . . ?
N4 C13 C14 121.8(4) . . ?
N3 C13 C14 125.0(4) . . ?
C15 C14 C13 131.6(5) . . ?
C15 C14 S1 111.6(4) . . ?
C13 C14 S1 116.8(4) . . ?
C14 C15 C16 113.0(5) . . ?
C14 C15 H15 123.5 . . ?
C16 C15 H15 123.5 . . ?
C17 C16 C15 113.5(5) . . ?
C17 C16 H16 123.3 . . ?
C15 C16 H16 123.3 . . ?
C16 C17 C18 126.7(5) . . ?
C16 C17 S1 109.7(4) . . ?
C18 C17 S1 123.7(4) . . ?
C19 C18 O1 120.6(5) . . ?
C19 C18 C17 127.2(6) . . ?
O1 C18 C17 112.2(4) . . ?
C18 C19 C20 104.9(6) . . ?
C18 C19 H19 127.6 . . ?
C20 C19 H19 127.6 . . ?
C21 C20 C19 107.4(6) . . ?
C21 C20 H20 126.3 . . ?
C19 C20 H20 126.3 . . ?
C20 C21 C22 132.1(7) . . ?
C20 C21 O1 115.4(6) . . ?
C22 C21 O1 112.5(6) . . ?
O2 C22 C21 120.6(9) . . ?
O2 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
N3 C23 C24 114.4(4) . . ?
N3 C23 H23A 108.7 . . ?
C24 C23 H23A 108.7 . . ?
N3 C23 H23B 108.7 . . ?
C24 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C23 C24 C25 110.2(4) . . ?
C23 C24 H24A 109.6 . . ?
C25 C24 H24A 109.6 . . ?
C23 C24 H24B 109.6 . . ?
C25 C24 H24B 109.6 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 C26 113.5(5) . . ?
C24 C25 H25A 108.9 . . ?
C26 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
C26 C25 H25B 108.9 . . ?
H25A C25 H25B 107.7 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C12 118.5(5) . . ?
C10 N2 C11 117.5(5) . . ?
C5 N3 C13 105.6(4) . . ?
C5 N3 C23 126.5(4) . . ?
C13 N3 C23 126.9(4) . . ?
C13 N4 C6 104.7(4) . . ?
C21 O1 C18 91.6(4) . . ?
C14 S1 C17 92.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.358
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.106
####################################################################### 
# 
# 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_13
_database_code_depnum_ccdc_archive 'CCDC 1018245'
_audit_update_record             
;
2014-08-06 deposited with the CCDC.
2014-12-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H25 Cl3 N4 S2'
_chemical_formula_sum            'C34 H25 Cl3 N4 S2'
_chemical_formula_weight         660.05

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_space_group_name_Hall  '-P 2ybc'


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

_cell_length_a                   9.5995(16)
_cell_length_b                   10.9578(19)
_cell_length_c                   29.580(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.350(2)
_cell_angle_gamma                90.00
_cell_volume                     3106.2(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5452
_cell_measurement_theta_min      2.477
_cell_measurement_theta_max      23.505

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    0.461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9425
_exptl_absorpt_correction_T_max  0.9553
_exptl_absorpt_process_details   'SADABS, BRUKER(2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'BRUKER Smart Apex CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22247
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.38
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5452
_reflns_number_gt                3950
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (BRUKER 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (BRUKER 2000)'
_computing_structure_solution    'SHELXTL (BRUKER 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0617P)²+0.7019P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5452
_refine_ls_number_parameters     389
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1208
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0974(3) 0.0645(3) -0.10936(10) 0.0615(8) Uani 1 1 d . . .
H1 H 0.0399 0.0213 -0.1301 0.074 Uiso 1 1 calc R . .
C2 C 0.0397(3) 0.1616(3) -0.08730(9) 0.0581(7) Uani 1 1 d . . .
H2 H -0.0534 0.1828 -0.0934 0.070 Uiso 1 1 calc R . .
C3 C 0.1216(3) 0.2261(3) -0.05638(9) 0.0502(7) Uani 1 1 d . . .
H3 H 0.0858 0.2922 -0.0411 0.060 Uiso 1 1 calc R . .
C4 C 0.2611(2) 0.1900(2) -0.04824(8) 0.0416(6) Uani 1 1 d . . .
C5 C 0.3552(2) 0.2489(2) -0.01582(8) 0.0400(6) Uani 1 1 d . . .
C6 C 0.4926(2) 0.2138(2) -0.00948(8) 0.0393(6) Uani 1 1 d . . .
C7 C 0.5500(2) 0.1166(2) -0.03496(8) 0.0412(6) Uani 1 1 d . . .
C8 C 0.6901(3) 0.0770(3) -0.03238(10) 0.0533(7) Uani 1 1 d . . .
H8 H 0.7558 0.1161 -0.0131 0.064 Uiso 1 1 calc R . .
C9 C 0.7286(3) -0.0182(3) -0.05813(10) 0.0580(7) Uani 1 1 d . . .
H9 H 0.8208 -0.0447 -0.0567 0.070 Uiso 1 1 calc R . .
C10 C 0.6299(3) -0.0754(3) -0.08649(10) 0.0576(7) Uani 1 1 d . . .
H10 H 0.6579 -0.1416 -0.1034 0.069 Uiso 1 1 calc R . .
C11 C 0.4571(3) 0.0542(2) -0.06589(8) 0.0414(6) Uani 1 1 d . . .
C12 C 0.3112(3) 0.0912(2) -0.07261(8) 0.0413(6) Uani 1 1 d . . .
C13 C 0.4428(3) 0.3667(2) 0.03511(8) 0.0419(6) Uani 1 1 d . . .
C14 C 0.4547(3) 0.4629(2) 0.06901(8) 0.0434(6) Uani 1 1 d . . .
C15 C 0.5632(3) 0.5325(2) 0.08571(9) 0.0516(7) Uani 1 1 d . . .
H15 H 0.6545 0.5220 0.0775 0.062 Uiso 1 1 calc R . .
C16 C 0.5241(3) 0.6212(3) 0.11647(9) 0.0541(7) Uani 1 1 d . . .
H16 H 0.5873 0.6758 0.1304 0.065 Uiso 1 1 calc R . .
C17 C 0.3858(3) 0.6210(2) 0.12434(8) 0.0444(6) Uani 1 1 d . . .
C18 C 0.3122(3) 0.7071(2) 0.15250(8) 0.0475(6) Uani 1 1 d . . .
C19 C 0.3745(3) 0.8179(3) 0.16373(10) 0.0627(8) Uani 1 1 d . . .
H19 H 0.4630 0.8339 0.1539 0.075 Uiso 1 1 calc R . .
C20 C 0.3105(4) 0.9054(3) 0.18886(11) 0.0732(9) Uani 1 1 d . . .
H20 H 0.3563 0.9784 0.1958 0.088 Uiso 1 1 calc R . .
C21 C 0.1797(3) 0.8853(3) 0.20365(11) 0.0688(9) Uani 1 1 d . . .
H21 H 0.1364 0.9449 0.2203 0.083 Uiso 1 1 calc R . .
C22 C 0.1128(3) 0.7767(3) 0.19383(8) 0.0520(7) Uani 1 1 d . . .
C23 C -0.0243(3) 0.7382(3) 0.20592(9) 0.0555(7) Uani 1 1 d . . .
C24 C -0.1209(4) 0.8009(4) 0.23029(11) 0.0742(9) Uani 1 1 d . . .
H24 H -0.0997 0.8781 0.2418 0.089 Uiso 1 1 calc R . .
C25 C -0.2468(4) 0.7490(4) 0.23722(13) 0.0863(11) Uani 1 1 d . . .
H25 H -0.3112 0.7912 0.2535 0.104 Uiso 1 1 calc R . .
C26 C -0.2800(4) 0.6348(4) 0.22041(13) 0.0846(11) Uani 1 1 d . . .
H26 H -0.3665 0.6011 0.2256 0.102 Uiso 1 1 calc R . .
C27 C -0.1874(3) 0.5701(3) 0.19617(11) 0.0711(9) Uani 1 1 d . . .
H27 H -0.2101 0.4932 0.1846 0.085 Uiso 1 1 calc R . .
C28 C -0.0590(3) 0.6225(3) 0.18935(9) 0.0558(7) Uani 1 1 d . . .
C29 C 0.1791(3) 0.6871(2) 0.16852(8) 0.0458(6) Uani 1 1 d . . .
C30 C 0.6885(2) 0.2850(2) 0.04719(8) 0.0440(6) Uani 1 1 d . . .
H30A H 0.7178 0.2004 0.0493 0.053 Uiso 1 1 calc R . .
H30B H 0.6827 0.3159 0.0778 0.053 Uiso 1 1 calc R . .
C31 C 0.7977(3) 0.3574(3) 0.02366(9) 0.0489(6) Uani 1 1 d . . .
H31A H 0.8193 0.3155 -0.0040 0.059 Uiso 1 1 calc R . .
H31B H 0.7596 0.4368 0.0153 0.059 Uiso 1 1 calc R . .
C32 C 0.9310(3) 0.3748(3) 0.05291(12) 0.0663(8) Uani 1 1 d . . .
H32A H 0.9934 0.4267 0.0368 0.080 Uiso 1 1 calc R . .
H32B H 0.9088 0.4172 0.0804 0.080 Uiso 1 1 calc R . .
C33 C 1.0062(3) 0.2587(3) 0.06581(13) 0.0800(10) Uani 1 1 d . . .
H33A H 0.9512 0.2121 0.0857 0.120 Uiso 1 1 calc R . .
H33B H 1.0947 0.2777 0.0809 0.120 Uiso 1 1 calc R . .
H33C H 1.0206 0.2119 0.0390 0.120 Uiso 1 1 calc R . .
C34 C 0.6758(3) 0.1644(3) 0.17793(10) 0.0671(8) Uani 1 1 d . . .
H34 H 0.6601 0.1130 0.1510 0.081 Uiso 1 1 calc R . .
Cl1 Cl 0.55957(12) 0.28745(10) 0.17441(4) 0.1006(3) Uani 1 1 d . . .
Cl2 Cl 0.64631(13) 0.07844(12) 0.22597(4) 0.1086(4) Uani 1 1 d . . .
Cl3 Cl 0.84723(10) 0.21744(12) 0.18061(4) 0.1076(4) Uani 1 1 d . . .
N1 N 0.2289(2) 0.0284(2) -0.10308(7) 0.0537(6) Uani 1 1 d . . .
N2 N 0.4980(2) -0.0415(2) -0.09098(7) 0.0503(5) Uani 1 1 d . . .
N3 N 0.3251(2) 0.3435(2) 0.01169(7) 0.0451(5) Uani 1 1 d . . .
N4 N 0.5495(2) 0.29062(18) 0.02385(6) 0.0411(5) Uani 1 1 d . . .
S1 S 0.30210(7) 0.50806(7) 0.09209(2) 0.0518(2) Uani 1 1 d . . .
S2 S 0.07480(8) 0.55732(7) 0.16006(3) 0.0575(2) 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
C1 N1 1.325(4) . ?
C1 C2 1.381(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.403(3) . ?
C3 H3 0.9300 . ?
C4 C12 1.402(3) . ?
C4 C5 1.431(3) . ?
C5 N3 1.360(3) . ?
C5 C6 1.377(3) . ?
C6 N4 1.384(3) . ?
C6 C7 1.433(3) . ?
C7 C8 1.411(3) . ?
C7 C11 1.416(3) . ?
C8 C9 1.356(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.379(4) . ?
C9 H9 0.9300 . ?
C10 N2 1.318(4) . ?
C10 H10 0.9300 . ?
C11 N2 1.356(3) . ?
C11 C12 1.460(3) . ?
C12 N1 1.352(3) . ?
C13 N3 1.315(3) . ?
C13 N4 1.377(3) . ?
C13 C14 1.455(4) . ?
C14 C15 1.360(4) . ?
C14 S1 1.725(2) . ?
C15 C16 1.398(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.362(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.467(4) . ?
C17 S1 1.731(3) . ?
C18 C19 1.385(4) . ?
C18 C29 1.406(4) . ?
C19 C20 1.380(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.371(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.375(4) . ?
C21 H21 0.9300 . ?
C22 C29 1.408(4) . ?
C22 C23 1.446(4) . ?
C23 C24 1.389(4) . ?
C23 C28 1.393(4) . ?
C24 C25 1.362(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.377(6) . ?
C25 H25 0.9300 . ?
C26 C27 1.372(5) . ?
C26 H26 0.9300 . ?
C27 C28 1.385(4) . ?
C27 H27 0.9300 . ?
C28 S2 1.744(3) . ?
C29 S2 1.749(3) . ?
C30 N4 1.467(3) . ?
C30 C31 1.516(4) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.514(4) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 C33 1.502(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C34 Cl2 1.742(3) . ?
C34 Cl3 1.743(3) . ?
C34 Cl1 1.749(4) . ?
C34 H34 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 124.7(3) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C3 C2 C1 118.9(3) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 118.4(3) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C12 C4 C3 118.8(2) . . ?
C12 C4 C5 118.1(2) . . ?
C3 C4 C5 123.1(2) . . ?
N3 C5 C6 111.5(2) . . ?
N3 C5 C4 126.6(2) . . ?
C6 C5 C4 121.9(2) . . ?
C5 C6 N4 105.2(2) . . ?
C5 C6 C7 122.0(2) . . ?
N4 C6 C7 132.7(2) . . ?
C8 C7 C11 116.6(2) . . ?
C8 C7 C6 126.5(2) . . ?
C11 C7 C6 116.9(2) . . ?
C9 C8 C7 119.8(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N2 C10 C9 123.7(3) . . ?
N2 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
N2 C11 C7 122.4(2) . . ?
N2 C11 C12 116.5(2) . . ?
C7 C11 C12 121.1(2) . . ?
N1 C12 C4 122.1(2) . . ?
N1 C12 C11 117.9(2) . . ?
C4 C12 C11 120.0(2) . . ?
N3 C13 N4 112.6(2) . . ?
N3 C13 C14 122.3(2) . . ?
N4 C13 C14 125.2(2) . . ?
C15 C14 C13 133.2(2) . . ?
C15 C14 S1 110.22(19) . . ?
C13 C14 S1 116.51(19) . . ?
C14 C15 C16 113.4(2) . . ?
C14 C15 H15 123.3 . . ?
C16 C15 H15 123.3 . . ?
C17 C16 C15 114.3(3) . . ?
C17 C16 H16 122.9 . . ?
C15 C16 H16 122.9 . . ?
C16 C17 C18 127.0(2) . . ?
C16 C17 S1 109.5(2) . . ?
C18 C17 S1 123.3(2) . . ?
C19 C18 C29 116.4(2) . . ?
C19 C18 C17 119.0(2) . . ?
C29 C18 C17 124.6(2) . . ?
C20 C19 C18 122.6(3) . . ?
C20 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
C21 C20 C19 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C22 119.7(3) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C29 119.7(3) . . ?
C21 C22 C23 128.3(3) . . ?
C29 C22 C23 112.0(2) . . ?
C24 C23 C28 118.6(3) . . ?
C24 C23 C22 129.0(3) . . ?
C28 C23 C22 112.4(2) . . ?
C25 C24 C23 119.8(4) . . ?
C25 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C24 C25 C26 121.0(4) . . ?
C24 C25 H25 119.5 . . ?
C26 C25 H25 119.5 . . ?
C27 C26 C25 121.0(4) . . ?
C27 C26 H26 119.5 . . ?
C25 C26 H26 119.5 . . ?
C26 C27 C28 118.1(4) . . ?
C26 C27 H27 121.0 . . ?
C28 C27 H27 121.0 . . ?
C27 C28 C23 121.6(3) . . ?
C27 C28 S2 126.1(3) . . ?
C23 C28 S2 112.3(2) . . ?
C18 C29 C22 121.2(2) . . ?
C18 C29 S2 127.0(2) . . ?
C22 C29 S2 111.7(2) . . ?
N4 C30 C31 113.3(2) . . ?
N4 C30 H30A 108.9 . . ?
C31 C30 H30A 108.9 . . ?
N4 C30 H30B 108.9 . . ?
C31 C30 H30B 108.9 . . ?
H30A C30 H30B 107.7 . . ?
C32 C31 C30 112.8(2) . . ?
C32 C31 H31A 109.0 . . ?
C30 C31 H31A 109.0 . . ?
C32 C31 H31B 109.0 . . ?
C30 C31 H31B 109.0 . . ?
H31A C31 H31B 107.8 . . ?
C33 C32 C31 114.6(3) . . ?
C33 C32 H32A 108.6 . . ?
C31 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C31 C32 H32B 108.6 . . ?
H32A C32 H32B 107.6 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C32 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
Cl2 C34 Cl3 109.94(18) . . ?
Cl2 C34 Cl1 109.39(18) . . ?
Cl3 C34 Cl1 110.05(19) . . ?
Cl2 C34 H34 109.1 . . ?
Cl3 C34 H34 109.1 . . ?
Cl1 C34 H34 109.1 . . ?
C1 N1 C12 117.2(2) . . ?
C10 N2 C11 118.0(2) . . ?
C13 N3 C5 104.9(2) . . ?
C13 N4 C6 105.81(19) . . ?
C13 N4 C30 125.5(2) . . ?
C6 N4 C30 128.3(2) . . ?
C14 S1 C17 92.62(13) . . ?
C28 S2 C29 91.60(14) . . ?

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
N1 C1 C2 C3 -0.5(5) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
C2 C3 C4 C12 1.1(4) . . . . ?
C2 C3 C4 C5 -178.3(2) . . . . ?
C12 C4 C5 N3 -178.2(2) . . . . ?
C3 C4 C5 N3 1.3(4) . . . . ?
C12 C4 C5 C6 2.5(4) . . . . ?
C3 C4 C5 C6 -178.0(2) . . . . ?
N3 C5 C6 N4 0.4(3) . . . . ?
C4 C5 C6 N4 179.8(2) . . . . ?
N3 C5 C6 C7 -179.3(2) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C8 177.3(3) . . . . ?
N4 C6 C7 C8 -2.3(4) . . . . ?
C5 C6 C7 C11 -2.6(4) . . . . ?
N4 C6 C7 C11 177.9(2) . . . . ?
C11 C7 C8 C9 -1.4(4) . . . . ?
C6 C7 C8 C9 178.8(3) . . . . ?
C7 C8 C9 C10 -0.2(4) . . . . ?
C8 C9 C10 N2 1.3(5) . . . . ?
C8 C7 C11 N2 2.0(4) . . . . ?
C6 C7 C11 N2 -178.2(2) . . . . ?
C8 C7 C11 C12 -177.4(2) . . . . ?
C6 C7 C11 C12 2.5(3) . . . . ?
C3 C4 C12 N1 -1.1(4) . . . . ?
C5 C4 C12 N1 178.4(2) . . . . ?
C3 C4 C12 C11 178.0(2) . . . . ?
C5 C4 C12 C11 -2.4(3) . . . . ?
N2 C11 C12 N1 -0.2(3) . . . . ?
C7 C11 C12 N1 179.2(2) . . . . ?
N2 C11 C12 C4 -179.4(2) . . . . ?
C7 C11 C12 C4 0.0(4) . . . . ?
N3 C13 C14 C15 -153.2(3) . . . . ?
N4 C13 C14 C15 26.9(4) . . . . ?
N3 C13 C14 S1 22.8(3) . . . . ?
N4 C13 C14 S1 -157.1(2) . . . . ?
C13 C14 C15 C16 175.9(3) . . . . ?
S1 C14 C15 C16 -0.3(3) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C16 C17 C18 -176.0(2) . . . . ?
C15 C16 C17 S1 -0.6(3) . . . . ?
C16 C17 C18 C19 17.9(4) . . . . ?
S1 C17 C18 C19 -156.9(2) . . . . ?
C16 C17 C18 C29 -163.7(3) . . . . ?
S1 C17 C18 C29 21.5(4) . . . . ?
C29 C18 C19 C20 -0.6(4) . . . . ?
C17 C18 C19 C20 177.9(3) . . . . ?
C18 C19 C20 C21 -0.4(5) . . . . ?
C19 C20 C21 C22 0.8(5) . . . . ?
C20 C21 C22 C29 -0.2(5) . . . . ?
C20 C21 C22 C23 -179.6(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C29 C22 C23 C24 -179.6(3) . . . . ?
C21 C22 C23 C28 178.8(3) . . . . ?
C29 C22 C23 C28 -0.6(3) . . . . ?
C28 C23 C24 C25 -0.4(5) . . . . ?
C22 C23 C24 C25 178.5(3) . . . . ?
C23 C24 C25 C26 0.0(5) . . . . ?
C24 C25 C26 C27 0.0(6) . . . . ?
C25 C26 C27 C28 0.4(5) . . . . ?
C26 C27 C28 C23 -0.8(5) . . . . ?
C26 C27 C28 S2 179.6(2) . . . . ?
C24 C23 C28 C27 0.8(4) . . . . ?
C22 C23 C28 C27 -178.3(3) . . . . ?
C24 C23 C28 S2 -179.6(2) . . . . ?
C22 C23 C28 S2 1.3(3) . . . . ?
C19 C18 C29 C22 1.2(4) . . . . ?
C17 C18 C29 C22 -177.3(2) . . . . ?
C19 C18 C29 S2 -179.9(2) . . . . ?
C17 C18 C29 S2 1.6(4) . . . . ?
C21 C22 C29 C18 -0.8(4) . . . . ?
C23 C22 C29 C18 178.6(2) . . . . ?
C21 C22 C29 S2 -179.8(2) . . . . ?
C23 C22 C29 S2 -0.4(3) . . . . ?
N4 C30 C31 C32 167.0(2) . . . . ?
C30 C31 C32 C33 62.5(3) . . . . ?
C2 C1 N1 C12 0.5(4) . . . . ?
C4 C12 N1 C1 0.3(4) . . . . ?
C11 C12 N1 C1 -178.9(2) . . . . ?
C9 C10 N2 C11 -0.8(4) . . . . ?
C7 C11 N2 C10 -0.9(4) . . . . ?
C12 C11 N2 C10 178.4(2) . . . . ?
N4 C13 N3 C5 0.1(3) . . . . ?
C14 C13 N3 C5 -179.7(2) . . . . ?
C6 C5 N3 C13 -0.3(3) . . . . ?
C4 C5 N3 C13 -179.7(2) . . . . ?
N3 C13 N4 C6 0.1(3) . . . . ?
C14 C13 N4 C6 179.9(2) . . . . ?
N3 C13 N4 C30 -173.1(2) . . . . ?
C14 C13 N4 C30 6.8(4) . . . . ?
C5 C6 N4 C13 -0.3(3) . . . . ?
C7 C6 N4 C13 179.4(3) . . . . ?
C5 C6 N4 C30 172.7(2) . . . . ?
C7 C6 N4 C30 -7.7(4) . . . . ?
C31 C30 N4 C13 -98.3(3) . . . . ?
C31 C30 N4 C6 90.0(3) . . . . ?
C15 C14 S1 C17 -0.1(2) . . . . ?
C13 C14 S1 C17 -176.9(2) . . . . ?
C16 C17 S1 C14 0.4(2) . . . . ?
C18 C17 S1 C14 175.9(2) . . . . ?
C27 C28 S2 C29 178.3(3) . . . . ?
C23 C28 S2 C29 -1.3(2) . . . . ?
C18 C29 S2 C28 -178.0(2) . . . . ?
C22 C29 S2 C28 1.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.051

#===END











