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

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

data_9a
_database_code_depnum_ccdc_archive 'CCDC 1479803'
_audit_update_record             
;
2016-10-29 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

#============================================================================== 
_vrf_PLAT934_9a                  
;
PROBLEM: Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          6 Check 
RESPONSE: Apparently, the obtained data and refimed structure should are 
appropriate.  Thereby, this alert is considered to be coming from 
systematic errors.  
;
#============================================================================== 
# CHEMICAL DATA

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H30 Br2 N4 O2'
_chemical_formula_sum            'C26 H30 Br2 N4 O2'
_chemical_formula_weight         590.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   4.64320(8)
_cell_length_b                   34.6471(6)
_cell_length_c                   7.77338(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.4634(9)
_cell_angle_gamma                90
_cell_volume                     1248.25(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    12313
_cell_measurement_theta_min      5.11
_cell_measurement_theta_max      68.22

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_F_000             600
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    4.367
_shelx_estimated_absorpt_T_min   0.669
_shelx_estimated_absorpt_T_max   0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.521
_exptl_absorpt_correction_T_max  0.646
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            14180
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -41
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.106
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2297
_reflns_number_gt                2013
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_refine_special_details          
; 
    ENTER TEXT OF LETTER 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0863P)²+6.4439P] 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         2297
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0436
_refine_ls_wR_factor_ref         0.1460
_refine_ls_wR_factor_gt          0.1432
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.94784(10) 0.11861(2) 0.18037(6) 0.0280(2) Uani 1 1 d . . . . .
O1 O -0.0417(7) 0.04013(9) 0.7930(4) 0.0270(7) Uani 1 1 d . . . . .
N1 N 0.2992(7) 0.07023(10) 0.6413(4) 0.0181(7) Uani 1 1 d . . . . .
N2 N 0.6078(7) 0.09025(10) 0.4266(5) 0.0197(7) Uani 1 1 d . . . . .
C1 C 0.0973(9) 0.04208(11) 0.6660(5) 0.0189(8) Uani 1 1 d . . . . .
C2 C 0.0857(9) 0.01597(11) 0.5080(5) 0.0165(8) Uani 1 1 d . . . . .
C3 C 0.2917(8) 0.03343(11) 0.3933(5) 0.0168(8) Uani 1 1 d . . . . .
C4 C 0.4133(9) 0.06584(12) 0.4818(5) 0.0183(8) Uani 1 1 d . . . . .
C5 C 0.6877(9) 0.08254(12) 0.2685(5) 0.0188(8) Uani 1 1 d . . . . .
C6 C 0.5921(9) 0.05207(12) 0.1664(6) 0.0219(9) Uani 1 1 d . . . . .
H7 H 0.6612 0.0483 0.0578 0.026 Uiso 1 1 calc R U . . .
C7 C 0.3892(9) 0.02699(12) 0.2301(6) 0.0204(8) Uani 1 1 d . . . . .
H6 H 0.3199 0.0062 0.1642 0.025 Uiso 1 1 calc R U . . .
C8 C 0.3678(9) 0.10209(12) 0.7609(5) 0.0205(9) Uani 1 1 d . . . . .
H9A H 0.5757 0.1048 0.7762 0.025 Uiso 1 1 calc R U . . .
H9B H 0.2957 0.0959 0.8722 0.025 Uiso 1 1 calc R U . . .
C9 C 0.2382(10) 0.14039(12) 0.6982(6) 0.0253(9) Uani 1 1 d . . . . .
H10A H 0.3087 0.1466 0.5865 0.030 Uiso 1 1 calc R U . . .
H10B H 0.0300 0.1380 0.6845 0.030 Uiso 1 1 calc R U . . .
C10 C 0.3163(11) 0.17278(13) 0.8241(6) 0.0298(10) Uani 1 1 d . . . . .
H11A H 0.5247 0.1743 0.8410 0.036 Uiso 1 1 calc R U . . .
H11B H 0.2402 0.1667 0.9344 0.036 Uiso 1 1 calc R U . . .
C11 C 0.2003(12) 0.21204(13) 0.7633(7) 0.0334(11) Uani 1 1 d . . . . .
H12A H 0.2788 0.2182 0.6539 0.040 Uiso 1 1 calc R U . . .
H12B H -0.0078 0.2104 0.7445 0.040 Uiso 1 1 calc R U . . .
C12 C 0.2738(15) 0.24435(15) 0.8900(8) 0.0467(14) Uani 1 1 d . . . . .
H13A H 0.1892 0.2384 0.9980 0.056 Uiso 1 1 calc R U . . .
H13B H 0.4815 0.2451 0.9122 0.056 Uiso 1 1 calc R U . . .
C13 C 0.1716(19) 0.28389(16) 0.8308(9) 0.0608(19) Uani 1 1 d . . . . .
H14A H 0.2264 0.3026 0.9178 0.073 Uiso 1 1 calc R U . . .
H14B H 0.2582 0.2904 0.7256 0.073 Uiso 1 1 calc R U . . .
H14C H -0.0345 0.2837 0.8116 0.073 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C5 1.895(4) . ?
O1 C1 1.213(5) . ?
N1 C1 1.374(5) . ?
N1 C4 1.386(5) . ?
N1 C8 1.465(5) . ?
N2 C4 1.327(5) . ?
N2 C5 1.332(5) . ?
C1 C2 1.524(6) . ?
C2 C2 1.364(8) 3_556 ?
C2 C3 1.476(5) . ?
C3 C7 1.391(6) . ?
C3 C4 1.416(6) . ?
C5 C6 1.378(6) . ?
C6 C7 1.394(6) . ?
C6 H7 0.9300 . ?
C7 H6 0.9300 . ?
C8 C9 1.525(6) . ?
C8 H9A 0.9700 . ?
C8 H9B 0.9700 . ?
C9 C10 1.518(6) . ?
C9 H10A 0.9700 . ?
C9 H10B 0.9700 . ?
C10 C11 1.527(6) . ?
C10 H11A 0.9700 . ?
C10 H11B 0.9700 . ?
C11 C12 1.516(7) . ?
C11 H12A 0.9700 . ?
C11 H12B 0.9700 . ?
C12 C13 1.512(8) . ?
C12 H13A 0.9700 . ?
C12 H13B 0.9700 . ?
C13 H14A 0.9600 . ?
C13 H14B 0.9600 . ?
C13 H14C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C4 110.4(3) . . ?
C1 N1 C8 124.7(3) . . ?
C4 N1 C8 124.7(3) . . ?
C4 N2 C5 113.8(4) . . ?
O1 C1 N1 123.6(4) . . ?
O1 C1 C2 128.9(4) . . ?
N1 C1 C2 107.5(3) . . ?
C2 C2 C3 132.3(5) 3_556 . ?
C2 C2 C1 123.2(5) 3_556 . ?
C3 C2 C1 104.5(3) . . ?
C7 C3 C4 115.3(4) . . ?
C7 C3 C2 138.1(4) . . ?
C4 C3 C2 106.6(3) . . ?
N2 C4 N1 121.6(4) . . ?
N2 C4 C3 127.4(4) . . ?
N1 C4 C3 111.0(4) . . ?
N2 C5 C6 126.0(4) . . ?
N2 C5 Br1 114.9(3) . . ?
C6 C5 Br1 119.1(3) . . ?
C5 C6 C7 118.3(4) . . ?
C5 C6 H7 120.9 . . ?
C7 C6 H7 120.9 . . ?
C3 C7 C6 119.2(4) . . ?
C3 C7 H6 120.4 . . ?
C6 C7 H6 120.4 . . ?
N1 C8 C9 112.7(3) . . ?
N1 C8 H9A 109.0 . . ?
C9 C8 H9A 109.0 . . ?
N1 C8 H9B 109.0 . . ?
C9 C8 H9B 109.0 . . ?
H9A C8 H9B 107.8 . . ?
C10 C9 C8 111.3(4) . . ?
C10 C9 H10A 109.4 . . ?
C8 C9 H10A 109.4 . . ?
C10 C9 H10B 109.4 . . ?
C8 C9 H10B 109.4 . . ?
H10A C9 H10B 108.0 . . ?
C9 C10 C11 113.1(4) . . ?
C9 C10 H11A 109.0 . . ?
C11 C10 H11A 109.0 . . ?
C9 C10 H11B 109.0 . . ?
C11 C10 H11B 109.0 . . ?
H11A C10 H11B 107.8 . . ?
C12 C11 C10 113.3(4) . . ?
C12 C11 H12A 108.9 . . ?
C10 C11 H12A 108.9 . . ?
C12 C11 H12B 108.9 . . ?
C10 C11 H12B 108.9 . . ?
H12A C11 H12B 107.7 . . ?
C13 C12 C11 114.7(5) . . ?
C13 C12 H13A 108.6 . . ?
C11 C12 H13A 108.6 . . ?
C13 C12 H13B 108.6 . . ?
C11 C12 H13B 108.6 . . ?
H13A C12 H13B 107.6 . . ?
C12 C13 H14A 109.5 . . ?
C12 C13 H14B 109.5 . . ?
H14A C13 H14B 109.5 . . ?
C12 C13 H14C 109.5 . . ?
H14A C13 H14C 109.5 . . ?
H14B C13 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 -177.6(4) . . . . ?
C8 N1 C1 O1 -1.9(6) . . . . ?
C4 N1 C1 C2 1.8(4) . . . . ?
C8 N1 C1 C2 177.5(3) . . . . ?
O1 C1 C2 C2 -3.1(8) . . . 3_556 ?
N1 C1 C2 C2 177.6(5) . . . 3_556 ?
O1 C1 C2 C3 177.3(4) . . . . ?
N1 C1 C2 C3 -2.0(4) . . . . ?
C2 C2 C3 C7 2.8(9) 3_556 . . . ?
C1 C2 C3 C7 -177.7(5) . . . . ?
C2 C2 C3 C4 -178.1(6) 3_556 . . . ?
C1 C2 C3 C4 1.4(4) . . . . ?
C5 N2 C4 N1 -178.0(4) . . . . ?
C5 N2 C4 C3 1.0(6) . . . . ?
C1 N1 C4 N2 178.3(4) . . . . ?
C8 N1 C4 N2 2.6(6) . . . . ?
C1 N1 C4 C3 -0.9(5) . . . . ?
C8 N1 C4 C3 -176.6(4) . . . . ?
C7 C3 C4 N2 -0.2(6) . . . . ?
C2 C3 C4 N2 -179.5(4) . . . . ?
C7 C3 C4 N1 178.9(3) . . . . ?
C2 C3 C4 N1 -0.4(4) . . . . ?
C4 N2 C5 C6 -1.6(6) . . . . ?
C4 N2 C5 Br1 176.4(3) . . . . ?
N2 C5 C6 C7 1.3(7) . . . . ?
Br1 C5 C6 C7 -176.7(3) . . . . ?
C4 C3 C7 C6 -0.3(6) . . . . ?
C2 C3 C7 C6 178.8(4) . . . . ?
C5 C6 C7 C3 -0.2(6) . . . . ?
C1 N1 C8 C9 -104.0(4) . . . . ?
C4 N1 C8 C9 71.1(5) . . . . ?
N1 C8 C9 C10 -179.4(4) . . . . ?
C8 C9 C10 C11 177.9(4) . . . . ?
C9 C10 C11 C12 179.1(5) . . . . ?
C10 C11 C12 C13 177.8(6) . . . . ?

_refine_diff_density_max         0.875
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_6_T_DAII
_database_code_depnum_ccdc_archive 'CCDC 1479804'
_audit_update_record             
;
2016-10-29 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H36 N4 O2 S2'
_chemical_formula_moiety         'C34 H36 N4 O2 S2'
_chemical_formula_weight         596.80
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   5.02134(9)
_cell_length_b                   9.79352(18)
_cell_length_c                   16.0988(3)
_cell_angle_alpha                99.8742(10)
_cell_angle_beta                 98.6417(11)
_cell_angle_gamma                101.4850(10)
_cell_volume                     750.27(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7738
_cell_measurement_theta_min      4.71
_cell_measurement_theta_max      68.20
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             316.00
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_T_max  0.826

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            8771
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_min         4.710
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2692
_reflns_number_gt                2294
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1362
_refine_ls_wR_factor_gt          0.1286
_refine_ls_number_restraints     94
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2692
_refine_ls_number_parameters     228
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0860P)²+0.0154P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         0.27
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2588(6) 0.8695(3) 0.27340(15) 0.0465(4) Uani 0.558(2) 1 d D U P A 1
O1 O 0.9617(2) 0.32330(11) 0.11116(6) 0.0469(3) Uani 1 1 d . . . . .
N1 N 0.7273(2) 0.49245(12) 0.15162(7) 0.0369(3) Uani 1 1 d . . . . .
N2 N 0.5365(2) 0.69518(12) 0.16717(7) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.116(3) 1.0163(9) 0.2872(8) 0.0437(15) Uani 0.558(2) 1 d D U P A 1
H1 H 0.0225 1.0389 0.3315 0.052 Uiso 0.558(2) 1 calc R U P A 1
C2 C 0.155(4) 1.0952(17) 0.2267(9) 0.0489(19) Uani 0.558(2) 1 d D U P A 1
H2 H 0.0925 1.1781 0.2246 0.059 Uiso 0.558(2) 1 calc R U P A 1
C3 C 0.3654(3) 0.90698(15) 0.18408(9) 0.0390(4) Uani 1 1 d D U . . .
C4 C 0.5102(3) 0.81392(14) 0.13705(9) 0.0378(4) Uani 1 1 d . . . . .
C5 C 0.6196(3) 0.84573(16) 0.06639(10) 0.0461(4) Uani 1 1 d . . . . .
H5 H 0.5977 0.9281 0.0474 0.055 Uiso 1 1 calc R U . . .
C6 C 0.7607(3) 0.75664(16) 0.02376(9) 0.0445(4) Uani 1 1 d . . . . .
H6 H 0.8319 0.7781 -0.0238 0.053 Uiso 1 1 calc R U . . .
C7 C 0.7941(3) 0.63462(14) 0.05340(8) 0.0340(3) Uani 1 1 d . . . . .
C8 C 0.6746(3) 0.61415(14) 0.12594(8) 0.0344(3) Uani 1 1 d . . . . .
C9 C 0.9286(3) 0.51750(14) 0.03207(8) 0.0332(3) Uani 1 1 d . . . . .
C10 C 0.8820(3) 0.42948(14) 0.10024(9) 0.0360(3) Uani 1 1 d . . . . .
C11 C 0.6315(3) 0.43774(15) 0.22363(8) 0.0391(4) Uani 1 1 d . . . . .
H11A H 0.6488 0.3399 0.2187 0.047 Uiso 1 1 calc R U . . .
H11B H 0.4368 0.4376 0.2200 0.047 Uiso 1 1 calc R U . . .
C12 C 0.7900(3) 0.52347(15) 0.31070(9) 0.0435(4) Uani 1 1 d . . . . .
H12A H 0.7690 0.6208 0.3167 0.052 Uiso 1 1 calc R U . . .
H12B H 0.9853 0.5253 0.3144 0.052 Uiso 1 1 calc R U . . .
C13 C 0.6876(3) 0.46068(17) 0.38393(10) 0.0445(4) Uani 1 1 d . . . . .
H13A H 0.7537 0.5318 0.4368 0.053 Uiso 1 1 calc R U . . .
H13B H 0.4869 0.4403 0.3728 0.053 Uiso 1 1 calc R U . . .
C14 C 0.7785(3) 0.32549(16) 0.39684(9) 0.0416(4) Uani 1 1 d . . . . .
H14A H 0.9790 0.3447 0.4065 0.050 Uiso 1 1 calc R U . . .
H14B H 0.7073 0.2529 0.3448 0.050 Uiso 1 1 calc R U . . .
C15 C 0.6799(3) 0.26832(18) 0.47207(10) 0.0478(4) Uani 1 1 d . . . . .
H15A H 0.7327 0.3445 0.5228 0.057 Uiso 1 1 calc R U . . .
H15B H 0.4794 0.2389 0.4593 0.057 Uiso 1 1 calc R U . . .
C16 C 0.7960(4) 0.1442(2) 0.49153(12) 0.0621(5) Uani 1 1 d . . . . .
H16A H 0.7396 0.0671 0.4423 0.093 Uiso 1 1 calc R U . . .
H16B H 0.7279 0.1138 0.5396 0.093 Uiso 1 1 calc R U . . .
H16C H 0.9944 0.1728 0.5051 0.093 Uiso 1 1 calc R U . . .
C17 C 0.3021(18) 1.0351(8) 0.1669(5) 0.100(4) Uani 0.558(2) 1 d D U P A 1
H17 H 0.3516 1.0753 0.1215 0.120 Uiso 0.558(2) 1 calc R U P A 1
S1A S 0.3040(3) 1.05366(15) 0.15657(11) 0.0426(4) Uani 0.442(2) 1 d D U P A 2
C17A C 0.242(3) 0.8774(15) 0.2535(6) 0.053(3) Uani 0.442(2) 1 d D U P A 2
H17A H 0.2440 0.7969 0.2767 0.064 Uiso 0.442(2) 1 calc R U P A 2
C1A C 0.134(5) 1.089(2) 0.2362(11) 0.047(2) Uani 0.442(2) 1 d D U P A 2
H1A H 0.0625 1.1697 0.2468 0.056 Uiso 0.442(2) 1 calc R U P A 2
C2A C 0.113(4) 0.9877(12) 0.2833(11) 0.050(2) Uani 0.442(2) 1 d D U P A 2
H2A H 0.0247 0.9898 0.3301 0.061 Uiso 0.442(2) 1 calc R U P A 2


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C3 1.680(3) . ?
S1 C1 1.726(8) . ?
O1 C10 1.2162(16) . ?
N1 C10 1.3702(18) . ?
N1 C8 1.3867(16) . ?
N1 C11 1.4631(16) . ?
N2 C8 1.3148(18) . ?
N2 C4 1.3565(17) . ?
C1 C2 1.356(11) . ?
C1 H1 0.9300 . ?
C2 C17 1.420(12) . ?
C2 H2 0.9300 . ?
C3 C17A 1.403(10) . ?
C3 C17 1.415(7) . ?
C3 C4 1.458(2) . ?
C3 S1A 1.646(2) . ?
C4 C5 1.391(2) . ?
C5 C6 1.386(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.3910(19) . ?
C6 H6 0.9300 . ?
C7 C8 1.4164(18) . ?
C7 C9 1.4606(18) . ?
C9 C9 1.377(3) 2_765 ?
C9 C10 1.5243(19) . ?
C11 C12 1.5160(19) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.5289(19) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.520(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.5257(19) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.507(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17 0.9300 . ?
S1A C1A 1.668(13) . ?
C17A C2A 1.416(14) . ?
C17A H17A 0.9300 . ?
C1A C2A 1.349(14) . ?
C1A H1A 0.9300 . ?
C2A H2A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C1 92.2(5) . . ?
C10 N1 C8 110.80(11) . . ?
C10 N1 C11 124.20(11) . . ?
C8 N1 C11 125.00(11) . . ?
C8 N2 C4 115.58(12) . . ?
C2 C1 S1 112.8(10) . . ?
C2 C1 H1 123.6 . . ?
S1 C1 H1 123.6 . . ?
C1 C2 C17 111.4(11) . . ?
C1 C2 H2 124.3 . . ?
C17 C2 H2 124.3 . . ?
C17A C3 C4 124.6(5) . . ?
C17 C3 C4 128.7(4) . . ?
C17A C3 S1A 111.5(5) . . ?
C4 C3 S1A 123.70(12) . . ?
C17 C3 S1 111.2(4) . . ?
C4 C3 S1 120.11(14) . . ?
N2 C4 C5 121.76(13) . . ?
N2 C4 C3 116.02(13) . . ?
C5 C4 C3 122.21(14) . . ?
C6 C5 C4 121.03(14) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 118.79(14) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
C6 C7 C8 114.91(13) . . ?
C6 C7 C9 137.69(13) . . ?
C8 C7 C9 107.37(11) . . ?
N2 C8 N1 121.96(12) . . ?
N2 C8 C7 127.92(13) . . ?
N1 C8 C7 110.11(12) . . ?
C9 C9 C7 132.55(15) 2_765 . ?
C9 C9 C10 122.93(15) 2_765 . ?
C7 C9 C10 104.52(11) . . ?
O1 C10 N1 123.39(13) . . ?
O1 C10 C9 129.44(13) . . ?
N1 C10 C9 107.17(11) . . ?
N1 C11 C12 113.43(12) . . ?
N1 C11 H11A 108.9 . . ?
C12 C11 H11A 108.9 . . ?
N1 C11 H11B 108.9 . . ?
C12 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C11 C12 C13 111.66(12) . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
C13 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
C14 C13 C12 114.65(13) . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C12 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 C15 113.23(13) . . ?
C13 C14 H14A 108.9 . . ?
C15 C14 H14A 108.9 . . ?
C13 C14 H14B 108.9 . . ?
C15 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C16 C15 C14 113.48(13) . . ?
C16 C15 H15A 108.9 . . ?
C14 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
C14 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C3 C17 C2 112.4(8) . . ?
C3 C17 H17 123.8 . . ?
C2 C17 H17 123.8 . . ?
C3 S1A C1A 93.7(6) . . ?
C3 C17A C2A 110.3(11) . . ?
C3 C17A H17A 124.8 . . ?
C2A C17A H17A 124.8 . . ?
C2A C1A S1A 112.0(13) . . ?
C2A C1A H1A 124.0 . . ?
S1A C1A H1A 124.0 . . ?
C1A C2A C17A 112.3(14) . . ?
C1A C2A H2A 123.8 . . ?
C17A C2A H2A 123.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 S1 C1 C2 -1.7(11) . . . . ?
S1 C1 C2 C17 0.4(17) . . . . ?
C1 S1 C3 C17 2.5(6) . . . . ?
C1 S1 C3 C4 -179.3(4) . . . . ?
C8 N2 C4 C5 0.9(2) . . . . ?
C8 N2 C4 C3 -178.02(12) . . . . ?
C17A C3 C4 N2 -3.7(7) . . . . ?
C17 C3 C4 N2 -178.5(4) . . . . ?
S1A C3 C4 N2 -178.23(12) . . . . ?
S1 C3 C4 N2 3.6(2) . . . . ?
C17A C3 C4 C5 177.4(7) . . . . ?
C17 C3 C4 C5 2.6(5) . . . . ?
S1A C3 C4 C5 2.8(2) . . . . ?
S1 C3 C4 C5 -175.36(17) . . . . ?
N2 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 C6 178.83(14) . . . . ?
C4 C5 C6 C7 -0.6(3) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
C5 C6 C7 C9 -177.54(15) . . . . ?
C4 N2 C8 N1 177.39(11) . . . . ?
C4 N2 C8 C7 -1.3(2) . . . . ?
C10 N1 C8 N2 -177.96(12) . . . . ?
C11 N1 C8 N2 2.1(2) . . . . ?
C10 N1 C8 C7 0.90(16) . . . . ?
C11 N1 C8 C7 -179.08(12) . . . . ?
C6 C7 C8 N2 0.6(2) . . . . ?
C9 C7 C8 N2 179.15(13) . . . . ?
C6 C7 C8 N1 -178.14(11) . . . . ?
C9 C7 C8 N1 0.37(15) . . . . ?
C6 C7 C9 C9 -3.1(3) . . . 2_765 ?
C8 C7 C9 C9 178.90(19) . . . 2_765 ?
C6 C7 C9 C10 176.66(16) . . . . ?
C8 C7 C9 C10 -1.33(14) . . . . ?
C8 N1 C10 O1 177.92(13) . . . . ?
C11 N1 C10 O1 -2.1(2) . . . . ?
C8 N1 C10 C9 -1.72(15) . . . . ?
C11 N1 C10 C9 178.25(11) . . . . ?
C9 C9 C10 O1 2.0(3) 2_765 . . . ?
C7 C9 C10 O1 -177.75(14) . . . . ?
C9 C9 C10 N1 -178.34(16) 2_765 . . . ?
C7 C9 C10 N1 1.87(15) . . . . ?
C10 N1 C11 C12 105.59(16) . . . . ?
C8 N1 C11 C12 -74.44(17) . . . . ?
N1 C11 C12 C13 -178.72(12) . . . . ?
C11 C12 C13 C14 74.79(17) . . . . ?
C12 C13 C14 C15 178.27(13) . . . . ?
C13 C14 C15 C16 -173.44(13) . . . . ?
C4 C3 C17 C2 179.2(9) . . . . ?
S1 C3 C17 C2 -2.7(11) . . . . ?
C1 C2 C17 C3 1.4(17) . . . . ?
C17A C3 S1A C1A 3.2(11) . . . . ?
C4 C3 S1A C1A 178.4(9) . . . . ?
C4 C3 C17A C2A -178.6(9) . . . . ?
S1A C3 C17A C2A -3.5(13) . . . . ?
C3 S1A C1A C2A -2.1(17) . . . . ?
S1A C1A C2A C17A 0(2) . . . . ?
C3 C17A C2A C1A 2(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


####################################################################### 
# 
# 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_5_T_T_DAII
_database_code_depnum_ccdc_archive 'CCDC 1479805'
_audit_update_record             
;
2016-10-29 deposited with the CCDC.
2016-10-31 downloaded from the CCDC.
;

#==============================================================================
_vrf_PLAT230_5_5_T_T_DAII        
;
PROBLEM: Hirshfeld Test Diff for    C9     --  C10     ..       11.9 s.u.
RESPONSE: This is due to the slight rotational disorder of the thiophene ring, 
in which S and C atoms are disorderd.  Their occupancies are only 10 %, so that 
we failed to fix the structure.    
;
#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C34 H36 N4 O2 S2'
_chemical_formula_moiety         'C34 H36 N4 O2 S2'
_chemical_formula_weight         596.80
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   14.00800(15)
_cell_length_b                   5.00611(6)
_cell_length_c                   21.3879(3)
_cell_angle_alpha                90.0000
_cell_angle_beta                 104.3730(12)
_cell_angle_gamma                90.0000
_cell_volume                     1452.89(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4525
_cell_measurement_theta_min      4.29
_cell_measurement_theta_max      72.97
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.286
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.018
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    1.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.9d (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.772
_exptl_absorpt_correction_T_max  0.965

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.811
_diffrn_reflns_number            7498
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_theta_max         73.709
_diffrn_reflns_theta_min         4.268
_diffrn_reflns_theta_full        67.687
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2847
_reflns_number_gt                2605
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1359
_refine_ls_wR_factor_gt          0.1323
_refine_ls_number_restraints     40
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2847
_refine_ls_number_parameters     191
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0691P)²+1.8339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.59
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.25175(4) 0.87754(11) 0.53680(2) 0.02161(18) Uani 1 1 d . U . . .
O1 O 0.65167(10) -0.2939(3) 0.56836(7) 0.0185(3) Uani 1 1 d . . . . .
N1 N 0.61928(12) 0.0268(3) 0.63626(8) 0.0147(4) Uani 1 1 d . . . . .
N2 N 0.54886(13) 0.3764(3) 0.68419(8) 0.0165(4) Uani 1 1 d . . . . .
C1 C 0.60343(14) -0.1032(4) 0.57776(9) 0.0144(4) Uani 1 1 d . . . . .
C2 C 0.51717(14) 0.0359(4) 0.53172(9) 0.0138(4) Uani 1 1 d . . . . .
C3 C 0.48604(14) 0.2446(4) 0.57108(9) 0.0139(4) Uani 1 1 d . . . . .
C4 C 0.55083(14) 0.2282(4) 0.63349(9) 0.0143(4) Uani 1 1 d . . . . .
C5 C 0.47596(15) 0.5613(4) 0.67417(9) 0.0164(4) Uani 1 1 d . . . . .
H5 H 0.4718 0.6729 0.7093 0.020 Uiso 1 1 calc R U . . .
C6 C 0.40680(14) 0.5980(4) 0.61566(10) 0.0152(4) Uani 1 1 d . . . . .
C7 C 0.41259(14) 0.4352(4) 0.56299(9) 0.0153(4) Uani 1 1 d . . . . .
H7 H 0.3666 0.4562 0.5224 0.018 Uiso 1 1 calc R U . . .
C8 C 0.33019(15) 0.8029(4) 0.60999(10) 0.0163(4) Uani 1 1 d . U . . .
C9 C 0.30990(13) 0.9717(4) 0.65941(8) 0.0091(4) Uani 1 1 d . U . . .
H9 H 0.3444 0.9654 0.7036 0.011 Uiso 1 1 calc R U . . .
C10 C 0.23204(16) 1.1473(5) 0.63331(11) 0.0238(5) Uani 1 1 d . U . . .
H10 H 0.2079 1.2737 0.6588 0.029 Uiso 1 1 calc R U . . .
C11 C 0.19400(16) 1.1216(4) 0.56871(12) 0.0233(5) Uani 1 1 d . U . . .
H11 H 0.1415 1.2273 0.5443 0.028 Uiso 1 1 calc R U . . .
C13 C 0.69702(15) -0.0464(4) 0.69289(9) 0.0165(4) Uani 1 1 d . . . . .
H13A H 0.7213 -0.2275 0.6865 0.020 Uiso 1 1 calc R U . . .
H13B H 0.6691 -0.0525 0.7311 0.020 Uiso 1 1 calc R U . . .
C14 C 0.78374(15) 0.1490(4) 0.70603(10) 0.0180(4) Uani 1 1 d . . . . .
H14A H 0.7632 0.3179 0.7229 0.022 Uiso 1 1 calc R U . . .
H14B H 0.8385 0.0729 0.7398 0.022 Uiso 1 1 calc R U . . .
C16 C 0.82103(15) 0.2103(4) 0.64664(10) 0.0190(4) Uani 1 1 d . . . . .
H16A H 0.7668 0.2915 0.6134 0.023 Uiso 1 1 calc R U . . .
H16B H 0.8395 0.0407 0.6290 0.023 Uiso 1 1 calc R U . . .
C17 C 0.90974(16) 0.3988(5) 0.65988(11) 0.0220(5) Uani 1 1 d . . . . .
H17A H 0.8951 0.5580 0.6834 0.026 Uiso 1 1 calc R U . . .
H17B H 0.9674 0.3071 0.6878 0.026 Uiso 1 1 calc R U . . .
C20 C 0.93492(17) 0.4875(5) 0.59765(12) 0.0274(5) Uani 1 1 d . . . . .
H20A H 0.9519 0.3279 0.5753 0.033 Uiso 1 1 calc R U . . .
H20B H 0.8758 0.5701 0.5690 0.033 Uiso 1 1 calc R U . . .
C21 C 1.01998(17) 0.6857(5) 0.60787(13) 0.0312(5) Uani 1 1 d . . . . .
H21A H 1.0796 0.6037 0.6349 0.037 Uiso 1 1 calc R U . . .
H21B H 1.0034 0.8461 0.6292 0.037 Uiso 1 1 calc R U . . .
H21C H 1.0316 0.7347 0.5660 0.037 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.9d (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT Version 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.1 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2.1'

#==============================================================================
# MOLECULAR GEOMETRY

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.699(2) . ?
S1 C8 1.716(2) . ?
O1 C1 1.215(2) . ?
N1 C1 1.379(3) . ?
N1 C4 1.382(3) . ?
N1 C13 1.460(2) . ?
N2 C4 1.320(3) . ?
N2 C5 1.355(3) . ?
C1 C2 1.525(3) . ?
C2 C2 1.370(4) 3_656 ?
C2 C3 1.474(3) . ?
C3 C7 1.382(3) . ?
C3 C4 1.418(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.409(3) . ?
C6 C8 1.468(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.436(3) . ?
C9 C10 1.404(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.358(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.530(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C16 1.520(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C17 1.530(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C20 1.525(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C20 C21 1.524(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C11 S1 C8 92.93(11) . . ?
C1 N1 C4 110.60(16) . . ?
C1 N1 C13 123.58(17) . . ?
C4 N1 C13 125.80(16) . . ?
C4 N2 C5 115.00(17) . . ?
O1 C1 N1 123.40(18) . . ?
O1 C1 C2 129.52(18) . . ?
N1 C1 C2 107.08(16) . . ?
C2 C2 C3 132.1(2) 3_656 . ?
C2 C2 C1 123.1(2) 3_656 . ?
C3 C2 C1 104.73(16) . . ?
C7 C3 C4 116.13(18) . . ?
C7 C3 C2 137.25(18) . . ?
C4 C3 C2 106.60(17) . . ?
N2 C4 N1 122.05(18) . . ?
N2 C4 C3 127.00(19) . . ?
N1 C4 C3 110.95(17) . . ?
N2 C5 C6 124.15(18) . . ?
N2 C5 H5 117.9 . . ?
C6 C5 H5 117.9 . . ?
C5 C6 C7 118.51(19) . . ?
C5 C6 C8 119.88(18) . . ?
C7 C6 C8 121.62(18) . . ?
C3 C7 C6 119.21(18) . . ?
C3 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C9 C8 C6 128.67(18) . . ?
C9 C8 S1 110.16(14) . . ?
C6 C8 S1 121.14(15) . . ?
C10 C9 C8 110.61(17) . . ?
C10 C9 H9 124.7 . . ?
C8 C9 H9 124.7 . . ?
C11 C10 C9 114.5(2) . . ?
C11 C10 H10 122.7 . . ?
C9 C10 H10 122.7 . . ?
C10 C11 S1 111.78(17) . . ?
C10 C11 H11 124.1 . . ?
S1 C11 H11 124.1 . . ?
N1 C13 C14 112.74(16) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C16 C14 C13 113.41(17) . . ?
C16 C14 H14A 108.9 . . ?
C13 C14 H14A 108.9 . . ?
C16 C14 H14B 108.9 . . ?
C13 C14 H14B 108.9 . . ?
H14A C14 H14B 107.7 . . ?
C14 C16 C17 113.70(17) . . ?
C14 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C14 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C20 C17 C16 111.80(18) . . ?
C20 C17 H17A 109.3 . . ?
C16 C17 H17A 109.3 . . ?
C20 C17 H17B 109.3 . . ?
C16 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C21 C20 C17 114.0(2) . . ?
C21 C20 H20A 108.8 . . ?
C17 C20 H20A 108.8 . . ?
C21 C20 H20B 108.8 . . ?
C17 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 . . ?

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
C4 N1 C1 O1 -177.44(18) . . . . ?
C13 N1 C1 O1 1.4(3) . . . . ?
C4 N1 C1 C2 1.9(2) . . . . ?
C13 N1 C1 C2 -179.25(16) . . . . ?
O1 C1 C2 C2 -2.7(4) . . . 3_656 ?
N1 C1 C2 C2 178.0(2) . . . 3_656 ?
O1 C1 C2 C3 177.4(2) . . . . ?
N1 C1 C2 C3 -2.0(2) . . . . ?
C2 C2 C3 C7 3.2(5) 3_656 . . . ?
C1 C2 C3 C7 -176.9(2) . . . . ?
C2 C2 C3 C4 -178.6(3) 3_656 . . . ?
C1 C2 C3 C4 1.3(2) . . . . ?
C5 N2 C4 N1 -178.51(17) . . . . ?
C5 N2 C4 C3 0.4(3) . . . . ?
C1 N1 C4 N2 177.91(18) . . . . ?
C13 N1 C4 N2 -0.9(3) . . . . ?
C1 N1 C4 C3 -1.2(2) . . . . ?
C13 N1 C4 C3 -179.95(17) . . . . ?
C7 C3 C4 N2 -0.6(3) . . . . ?
C2 C3 C4 N2 -179.19(19) . . . . ?
C7 C3 C4 N1 178.42(16) . . . . ?
C2 C3 C4 N1 -0.2(2) . . . . ?
C4 N2 C5 C6 0.2(3) . . . . ?
N2 C5 C6 C7 -0.5(3) . . . . ?
N2 C5 C6 C8 179.54(18) . . . . ?
C4 C3 C7 C6 0.2(3) . . . . ?
C2 C3 C7 C6 178.2(2) . . . . ?
C5 C6 C7 C3 0.3(3) . . . . ?
C8 C6 C7 C3 -179.76(18) . . . . ?
C5 C6 C8 C9 -4.6(3) . . . . ?
C7 C6 C8 C9 175.40(19) . . . . ?
C5 C6 C8 S1 173.17(15) . . . . ?
C7 C6 C8 S1 -6.8(3) . . . . ?
C11 S1 C8 C9 0.18(16) . . . . ?
C11 S1 C8 C6 -178.00(17) . . . . ?
C6 C8 C9 C10 178.0(2) . . . . ?
S1 C8 C9 C10 0.0(2) . . . . ?
C8 C9 C10 C11 -0.3(3) . . . . ?
C9 C10 C11 S1 0.4(3) . . . . ?
C8 S1 C11 C10 -0.36(18) . . . . ?
C1 N1 C13 C14 104.8(2) . . . . ?
C4 N1 C13 C14 -76.6(2) . . . . ?
N1 C13 C14 C16 -48.8(2) . . . . ?
C13 C14 C16 C17 -178.21(18) . . . . ?
C14 C16 C17 C20 -171.47(19) . . . . ?
C16 C17 C20 C21 177.4(2) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


