# 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_aaw017
_database_code_depnum_ccdc_archive 'CCDC 1053866'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H28 Cl2 N4 O2 S3'
_chemical_formula_weight         595.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
O O 0.0106 0.0060 '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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   14.3594(3)
_cell_length_b                   22.1059(5)
_cell_length_c                   8.8264(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.710(2)
_cell_angle_gamma                90.00
_cell_volume                     2709.91(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7129
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.6

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1240
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.880
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.4383
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            21011
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0386
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.93
_diffrn_reflns_theta_max         25.69
_reflns_number_total             5140
_reflns_number_gt                3899
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0896P)²+4.4327P] 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       none
_refine_ls_number_reflns         5140
_refine_ls_number_parameters     362
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0576
_refine_ls_wR_factor_ref         0.1775
_refine_ls_wR_factor_gt          0.1556
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.2486(3) 0.51362(13) 0.7627(5) 0.0464(9) Uani 0.635(5) 1 d P A 1
S2 S 0.21063(6) 0.36301(4) 0.54401(10) 0.0276(2) Uani 1 1 d . A 1
S3 S 0.20766(12) 0.16677(8) 0.5988(2) 0.0337(5) Uani 0.804(5) 1 d P A 1
Cl1 Cl 0.88371(12) 0.18621(7) -0.04733(17) 0.0801(5) Uani 1 1 d . B 1
Cl2 Cl 0.89446(11) 0.31035(7) 0.05427(16) 0.0749(4) Uani 1 1 d . B 1
O1 O 0.44689(17) 0.14314(10) 0.9828(3) 0.0274(5) Uani 1 1 d . A 1
O2 O 0.62243(17) 0.26930(11) 1.3539(3) 0.0310(6) Uani 1 1 d . A 1
N1 N 0.34864(18) 0.24122(12) 0.8255(3) 0.0208(6) Uani 1 1 d . A 1
N2 N 0.41565(18) 0.35801(12) 0.9353(3) 0.0210(6) Uani 1 1 d . A 1
N3 N 0.52103(19) 0.31417(12) 1.1465(3) 0.0220(6) Uani 1 1 d . A 1
N4 N 0.53486(19) 0.20531(12) 1.1718(3) 0.0217(6) Uani 1 1 d . A 1
C1 C 0.3060(4) 0.5697(2) 0.7173(7) 0.0720(19) Uani 1 1 d D A 1
H1 H 0.2927 0.6101 0.7423 0.086 Uiso 1 1 calc R A 1
C2 C 0.3725(4) 0.5574(2) 0.6438(7) 0.0706(18) Uani 1 1 d D A 1
H2 H 0.4119 0.5858 0.6085 0.085 Uiso 1 1 calc R A 1
C3 C 0.3745(16) 0.4934(7) 0.627(3) 0.032(5) Uani 0.635(5) 1 d PD A 1
H3 H 0.4176 0.4739 0.5767 0.038 Uiso 1 1 calc R A 1
C4 C 0.3102(3) 0.46176(15) 0.6876(4) 0.0321(8) Uani 1 1 d D A 1
C5 C 0.2962(2) 0.39615(15) 0.6960(4) 0.0252(7) Uani 1 1 d . A 1
C6 C 0.3424(2) 0.35241(14) 0.7977(4) 0.0219(7) Uani 1 1 d . A 1
C7 C 0.3090(2) 0.29220(14) 0.7490(4) 0.0199(6) Uani 1 1 d . A 1
C8 C 0.2353(2) 0.29113(15) 0.6120(4) 0.0229(7) Uani 1 1 d . A 1
C9 C 0.1837(2) 0.23970(15) 0.5307(4) 0.0239(7) Uani 1 1 d D A 1
C10 C 0.1136(9) 0.2375(5) 0.3924(13) 0.029(3) Uani 0.804(5) 1 d PD A 1
H10 H 0.0892 0.2730 0.3355 0.034 Uiso 1 1 calc R A 1
C11 C 0.0800(3) 0.17967(19) 0.3399(4) 0.0380(9) Uani 1 1 d . A 1
H11 H 0.0320 0.1709 0.2467 0.046 Uiso 1 1 calc R A 1
C12 C 0.1276(3) 0.13859(18) 0.4442(5) 0.0402(9) Uani 1 1 d D A 1
H12 H 0.1161 0.0964 0.4305 0.048 Uiso 1 1 calc R A 1
C13 C 0.4506(2) 0.41762(14) 1.0015(4) 0.0239(7) Uani 1 1 d . A 1
H13A H 0.4431 0.4474 0.9155 0.029 Uiso 1 1 calc R A 1
H13B H 0.5200 0.4147 1.0549 0.029 Uiso 1 1 calc R A 1
C14 C 0.3960(3) 0.43959(16) 1.1173(4) 0.0321(8) Uani 1 1 d . A 1
H14A H 0.4210 0.4791 1.1587 0.048 Uiso 1 1 calc R A 1
H14B H 0.4043 0.4106 1.2037 0.048 Uiso 1 1 calc R A 1
H14C H 0.3274 0.4432 1.0644 0.048 Uiso 1 1 calc R A 1
C15 C 0.4543(2) 0.30718(14) 1.0165(4) 0.0199(6) Uani 1 1 d . A 1
C16 C 0.4182(2) 0.24857(14) 0.9513(4) 0.0202(6) Uani 1 1 d . A 1
C17 C 0.4667(2) 0.19374(14) 1.0331(4) 0.0205(7) Uani 1 1 d . A 1
C18 C 0.5623(2) 0.26415(14) 1.2289(4) 0.0223(7) Uani 1 1 d . A 1
C19 C 0.5883(2) 0.15359(15) 1.2564(4) 0.0238(7) Uani 1 1 d . A 1
H19A H 0.5485 0.1166 1.2303 0.029 Uiso 1 1 calc R A 1
H19B H 0.6003 0.1606 1.3705 0.029 Uiso 1 1 calc R A 1
C20 C 0.6844(2) 0.14367(15) 1.2155(4) 0.0246(7) Uani 1 1 d . A 1
H20A H 0.6743 0.1456 1.1004 0.030 Uiso 1 1 calc R A 1
H20B H 0.7296 0.1764 1.2625 0.030 Uiso 1 1 calc R A 1
C21 C 0.7286(2) 0.08273(16) 1.2748(4) 0.0291(8) Uani 1 1 d . A 1
H21A H 0.7417 0.0817 1.3904 0.035 Uiso 1 1 calc R A 1
H21B H 0.6818 0.0502 1.2322 0.035 Uiso 1 1 calc R A 1
C22 C 0.8217(2) 0.07073(16) 1.2275(4) 0.0335(8) Uani 1 1 d . A 1
H22A H 0.8695 0.1018 1.2765 0.040 Uiso 1 1 calc R A 1
H22B H 0.8092 0.0753 1.1125 0.040 Uiso 1 1 calc R A 1
C23 C 0.8652(3) 0.00848(17) 1.2734(5) 0.0388(9) Uani 1 1 d . A 1
H23A H 0.8150 -0.0227 1.2366 0.047 Uiso 1 1 calc R A 1
H23B H 0.8866 0.0058 1.3890 0.047 Uiso 1 1 calc R A 1
C24 C 0.9505(3) -0.0050(2) 1.2051(7) 0.0584(13) Uani 1 1 d . A 1
H24A H 0.9279 -0.0055 1.0894 0.070 Uiso 1 1 calc R A 1
H24B H 0.9982 0.0281 1.2346 0.070 Uiso 1 1 calc R A 1
C25 C 0.9995(3) -0.0641(2) 1.2593(7) 0.0597(13) Uani 1 1 d . A 1
H25A H 1.0531 -0.0700 1.2107 0.089 Uiso 1 1 calc R A 1
H25B H 0.9533 -0.0972 1.2290 0.089 Uiso 1 1 calc R A 1
H25C H 1.0242 -0.0635 1.3735 0.089 Uiso 1 1 calc R A 1
C26 C 0.8425(4) 0.2401(2) 0.0632(6) 0.0658(15) Uani 1 1 d . B 1
H26A H 0.7717 0.2437 0.0246 0.079 Uiso 1 1 calc R B 1
H26B H 0.8572 0.2266 0.1737 0.079 Uiso 1 1 calc R B 1
C3' C 0.2610(14) 0.5066(6) 0.746(3) 0.020(4) Uiso 0.365(5) 1 d PD A 2
C10' C 0.2014(18) 0.1802(7) 0.567(3) 0.021(8) Uiso 0.196(5) 1 d PD A 2
S1' S 0.3881(8) 0.4927(3) 0.6014(14) 0.0346(16) Uani 0.365(5) 1 d P A 2
S3' S 0.0963(10) 0.2495(5) 0.3651(15) 0.023(2) Uani 0.196(5) 1 d P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.595(8) . ?
S1 C4 1.683(5) . ?
S2 C8 1.704(3) . ?
S2 C5 1.735(3) . ?
S3 C12 1.666(4) . ?
S3 C9 1.724(4) . ?
Cl1 C26 1.736(6) . ?
Cl2 C26 1.733(5) . ?
O1 C17 1.210(4) . ?
O2 C18 1.222(4) . ?
N1 C16 1.302(4) . ?
N1 C7 1.362(4) . ?
N2 C15 1.372(4) . ?
N2 C6 1.396(4) . ?
N2 C13 1.477(4) . ?
N3 C15 1.304(4) . ?
N3 C18 1.372(4) . ?
N4 C17 1.383(4) . ?
N4 C18 1.414(4) . ?
N4 C19 1.470(4) . ?
C1 C2 1.313(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.422(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.372(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.469(5) . ?
C5 C6 1.370(5) . ?
C6 C7 1.443(4) . ?
C7 C8 1.390(4) . ?
C8 C9 1.444(5) . ?
C9 C10 1.372(10) . ?
C10 C11 1.402(13) . ?
C10 H10 0.9500 . ?
C11 C12 1.349(6) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.517(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.458(4) . ?
C16 C17 1.490(4) . ?
C19 C20 1.529(4) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.524(4) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.522(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.523(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.526(6) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.503(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?

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 S1 C4 94.3(3) . . ?
C8 S2 C5 94.49(15) . . ?
C12 S3 C9 91.7(2) . . ?
C16 N1 C7 117.0(3) . . ?
C15 N2 C6 119.8(3) . . ?
C15 N2 C13 118.2(2) . . ?
C6 N2 C13 121.9(3) . . ?
C15 N3 C18 119.5(3) . . ?
C17 N4 C18 123.8(3) . . ?
C17 N4 C19 117.8(3) . . ?
C18 N4 C19 118.2(3) . . ?
C2 C1 S1 116.7(4) . . ?
C2 C1 H1 121.7 . . ?
S1 C1 H1 121.7 . . ?
C1 C2 C3 107.2(8) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C4 C3 C2 115.6(13) . . ?
C4 C3 H3 122.2 . . ?
C2 C3 H3 122.2 . . ?
C3 C4 C5 129.6(8) . . ?
C3 C4 S1 106.2(8) . . ?
C5 C4 S1 124.1(3) . . ?
C6 C5 C4 132.9(3) . . ?
C6 C5 S2 109.8(2) . . ?
C4 C5 S2 117.2(2) . . ?
C5 C6 N2 129.8(3) . . ?
C5 C6 C7 112.8(3) . . ?
N2 C6 C7 117.5(3) . . ?
N1 C7 C8 123.2(3) . . ?
N1 C7 C6 123.4(3) . . ?
C8 C7 C6 113.4(3) . . ?
C7 C8 C9 128.8(3) . . ?
C7 C8 S2 109.6(2) . . ?
C9 C8 S2 121.7(2) . . ?
C10 C9 C8 129.6(6) . . ?
C10 C9 S3 108.2(5) . . ?
C8 C9 S3 122.1(2) . . ?
C9 C10 C11 116.1(7) . . ?
C9 C10 H10 122.0 . . ?
C11 C10 H10 122.0 . . ?
C12 C11 C10 108.4(5) . . ?
C12 C11 H11 125.8 . . ?
C10 C11 H11 125.8 . . ?
C11 C12 S3 115.6(3) . . ?
C11 C12 H12 122.2 . . ?
S3 C12 H12 122.2 . . ?
N2 C13 C14 111.8(3) . . ?
N2 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N2 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N3 C15 N2 118.1(3) . . ?
N3 C15 C16 124.1(3) . . ?
N2 C15 C16 117.8(3) . . ?
N1 C16 C15 124.5(3) . . ?
N1 C16 C17 118.4(3) . . ?
C15 C16 C17 117.2(3) . . ?
O1 C17 N4 122.9(3) . . ?
O1 C17 C16 122.5(3) . . ?
N4 C17 C16 114.6(3) . . ?
O2 C18 N3 121.0(3) . . ?
O2 C18 N4 118.5(3) . . ?
N3 C18 N4 120.6(3) . . ?
N4 C19 C20 112.2(3) . . ?
N4 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N4 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C21 C20 C19 111.6(3) . . ?
C21 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
C21 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 112.2(3) . . ?
C22 C21 H21A 109.2 . . ?
C20 C21 H21A 109.2 . . ?
C22 C21 H21B 109.2 . . ?
C20 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 114.5(3) . . ?
C21 C22 H22A 108.6 . . ?
C23 C22 H22A 108.6 . . ?
C21 C22 H22B 108.6 . . ?
C23 C22 H22B 108.6 . . ?
H22A C22 H22B 107.6 . . ?
C22 C23 C24 112.8(4) . . ?
C22 C23 H23A 109.0 . . ?
C24 C23 H23A 109.0 . . ?
C22 C23 H23B 109.0 . . ?
C24 C23 H23B 109.0 . . ?
H23A C23 H23B 107.8 . . ?
C25 C24 C23 113.7(4) . . ?
C25 C24 H24A 108.8 . . ?
C23 C24 H24A 108.8 . . ?
C25 C24 H24B 108.8 . . ?
C23 C24 H24B 108.8 . . ?
H24A C24 H24B 107.7 . . ?
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 . . ?
Cl2 C26 Cl1 112.2(3) . . ?
Cl2 C26 H26A 109.2 . . ?
Cl1 C26 H26A 109.2 . . ?
Cl2 C26 H26B 109.2 . . ?
Cl1 C26 H26B 109.2 . . ?
H26A C26 H26B 107.9 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.69
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.72
_refine_diff_density_min         -0.86
_refine_diff_density_rms         0.08
####################################################################### 
# 
# 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_bfttthept
_database_code_depnum_ccdc_archive 'CCDC 1053867'
_audit_update_record             
;
2015-03-13 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H25 Br N4 O2 S3'
_chemical_formula_weight         589.58

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'
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   P2(1)/c

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

_cell_length_a                   14.7336(8)
_cell_length_b                   18.2084(11)
_cell_length_c                   9.4057(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.715(3)
_cell_angle_gamma                90.00
_cell_volume                     2514.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5459
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.8

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1208
_exptl_absorpt_coefficient_mu    1.915
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_T_max  0.9448
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(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 Apex II Quasar'
_diffrn_measurement_method       'ω & π scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            19655
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_sigmaI/netI    0.0407
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4922
_reflns_number_gt                3972
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       Apex2
_computing_cell_refinement       Apex2
_computing_data_reduction        Apex2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    Diamond3
_computing_publication_material  WinGX

_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 > 2σ(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)+(0.0455P)²+3.6106P] 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       none
_refine_ls_number_reflns         4922
_refine_ls_number_parameters     318
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.0974
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.3054(2) 0.08967(15) 0.3510(3) 0.0184(7) Uani 1 1 d . . .
C2 C 0.3625(2) 0.12901(16) 0.4414(4) 0.0218(7) Uani 1 1 d . . .
H2 H 0.3437 0.1667 0.5024 0.026 Uiso 1 1 calc R . .
C3 C 0.4536(2) 0.10677(16) 0.4334(3) 0.0199(7) Uani 1 1 d . . .
H3 H 0.5035 0.1281 0.4891 0.024 Uiso 1 1 calc R . .
C4 C 0.4630(2) 0.05098(15) 0.3365(3) 0.0146(6) Uani 1 1 d . . .
C5 C 0.5468(2) 0.01843(15) 0.2954(3) 0.0152(6) Uani 1 1 d . . .
C6 C 0.5558(2) -0.03617(15) 0.1949(3) 0.0143(6) Uani 1 1 d . . .
C7 C 0.6482(2) -0.05359(15) 0.1724(3) 0.0145(6) Uani 1 1 d . . .
C8 C 0.7096(2) -0.01039(15) 0.2507(3) 0.0169(6) Uani 1 1 d . . .
C9 C 0.8078(2) 0.00147(16) 0.2442(4) 0.0192(7) Uani 1 1 d . . .
C10 C 0.8822(2) -0.02537(18) 0.3374(4) 0.0247(7) Uani 1 1 d . . .
H10 H 0.8767 -0.0556 0.4186 0.030 Uiso 1 1 calc R . .
C11 C 0.9654(2) 0.0004(2) 0.2892(4) 0.0337(9) Uani 1 1 d . . .
H11 H 1.0230 -0.0103 0.3376 0.040 Uiso 1 1 calc R . .
C12 C 0.9561(3) 0.0407(2) 0.1706(5) 0.0421(10) Uani 1 1 d . . .
H12 H 1.0061 0.0602 0.1254 0.051 Uiso 1 1 calc R . .
C13 C 0.7549(2) -0.14224(17) 0.0711(4) 0.0226(7) Uani 1 1 d . . .
H13A H 0.8006 -0.1024 0.0714 0.027 Uiso 1 1 calc R . .
H13B H 0.7570 -0.1703 -0.0187 0.027 Uiso 1 1 calc R . .
C14 C 0.7776(2) -0.19250(18) 0.1968(4) 0.0309(8) Uani 1 1 d . . .
H14A H 0.7780 -0.1642 0.2855 0.046 Uiso 1 1 calc R . .
H14B H 0.8378 -0.2144 0.1893 0.046 Uiso 1 1 calc R . .
H14C H 0.7317 -0.2315 0.1973 0.046 Uiso 1 1 calc R . .
C15 C 0.5904(2) -0.14372(15) 0.0047(3) 0.0139(6) Uani 1 1 d . . .
C16 C 0.5004(2) -0.11648(14) 0.0273(3) 0.0136(6) Uani 1 1 d . . .
C17 C 0.4212(2) -0.15005(15) -0.0570(3) 0.0158(6) Uani 1 1 d . . .
C18 C 0.5334(2) -0.23188(15) -0.1561(3) 0.0177(6) Uani 1 1 d . . .
C19 C 0.3680(2) -0.24074(17) -0.2346(3) 0.0211(7) Uani 1 1 d . . .
H19A H 0.3924 -0.2627 -0.3198 0.025 Uiso 1 1 calc R . .
H19B H 0.3235 -0.2024 -0.2679 0.025 Uiso 1 1 calc R . .
C20 C 0.3195(2) -0.29917(19) -0.1576(4) 0.0294(8) Uani 1 1 d . . .
H20A H 0.3001 -0.2788 -0.0673 0.035 Uiso 1 1 calc R . .
H20B H 0.3619 -0.3404 -0.1336 0.035 Uiso 1 1 calc R . .
C21 C 0.2362(2) -0.3277(2) -0.2483(4) 0.0329(9) Uani 1 1 d . . .
H21A H 0.2011 -0.2851 -0.2883 0.039 Uiso 1 1 calc R . .
H21B H 0.2574 -0.3559 -0.3294 0.039 Uiso 1 1 calc R . .
C22 C 0.1740(3) -0.3754(2) -0.1716(5) 0.0417(10) Uani 1 1 d . . .
H22A H 0.2105 -0.4149 -0.1225 0.050 Uiso 1 1 calc R . .
H22B H 0.1303 -0.3990 -0.2431 0.050 Uiso 1 1 calc R . .
C23 C 0.1196(3) -0.3360(2) -0.0609(4) 0.0395(9) Uani 1 1 d . . .
H23A H 0.0923 -0.3732 -0.0006 0.047 Uiso 1 1 calc R . .
H23B H 0.1617 -0.3056 0.0018 0.047 Uiso 1 1 calc R . .
C24 C 0.0448(4) -0.2875(3) -0.1291(6) 0.0616(13) Uani 1 1 d . . .
H24A H 0.0726 -0.2503 -0.1888 0.074 Uiso 1 1 calc R . .
H24B H 0.0036 -0.3181 -0.1931 0.074 Uiso 1 1 calc R . .
C25 C -0.0106(4) -0.2489(3) -0.0265(6) 0.0738(16) Uani 1 1 d . . .
H25A H -0.0328 -0.2846 0.0406 0.111 Uiso 1 1 calc R . .
H25B H -0.0625 -0.2247 -0.0788 0.111 Uiso 1 1 calc R . .
H25C H 0.0271 -0.2121 0.0263 0.111 Uiso 1 1 calc R . .
Br1 Br 0.17918(2) 0.101833(18) 0.31586(4) 0.02997(12) Uani 1 1 d . . .
N1 N 0.48248(17) -0.06669(12) 0.1198(3) 0.0145(5) Uani 1 1 d . . .
N2 N 0.66308(17) -0.11016(12) 0.0779(3) 0.0149(5) Uani 1 1 d . . .
N3 N 0.60531(17) -0.19906(13) -0.0791(3) 0.0163(5) Uani 1 1 d . . .
N4 N 0.44330(17) -0.20589(13) -0.1465(3) 0.0170(5) Uani 1 1 d . . .
O1 O 0.34378(15) -0.12965(12) -0.0482(2) 0.0218(5) Uani 1 1 d . . .
O2 O 0.54465(16) -0.28436(11) -0.2326(3) 0.0258(5) Uani 1 1 d . . .
S1 S 0.35802(5) 0.02415(4) 0.25545(8) 0.01794(17) Uani 1 1 d . . .
S2 S 0.65241(5) 0.04751(4) 0.36007(8) 0.01743(17) Uani 1 1 d . . .
S3 S 0.84625(7) 0.05361(7) 0.10834(13) 0.0504(3) Uani 1 1 d . . .


_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 1.351(5) . ?
C1 S1 1.717(3) . ?
C1 Br1 1.875(3) . ?
C2 C3 1.411(4) . ?
C3 C4 1.379(4) . ?
C4 C5 1.450(4) . ?
C4 S1 1.738(3) . ?
C5 C6 1.385(4) . ?
C5 S2 1.707(3) . ?
C6 N1 1.360(4) . ?
C6 C7 1.430(4) . ?
C7 C8 1.368(4) . ?
C7 N2 1.390(4) . ?
C8 C9 1.469(4) . ?
C8 S2 1.739(3) . ?
C9 C10 1.432(5) . ?
C9 S3 1.725(3) . ?
C10 C11 1.421(5) . ?
C11 C12 1.334(6) . ?
C12 S3 1.691(4) . ?
C13 N2 1.479(4) . ?
C13 C14 1.511(5) . ?
C15 N3 1.309(4) . ?
C15 N2 1.369(4) . ?
C15 C16 1.447(4) . ?
C16 N1 1.299(4) . ?
C16 C17 1.488(4) . ?
C17 O1 1.209(4) . ?
C17 N4 1.376(4) . ?
C18 O2 1.216(4) . ?
C18 N3 1.370(4) . ?
C18 N4 1.420(4) . ?
C19 N4 1.473(4) . ?
C19 C20 1.501(5) . ?
C20 C21 1.527(4) . ?
C21 C22 1.491(5) . ?
C22 C23 1.542(6) . ?
C23 C24 1.512(6) . ?
C24 C25 1.491(7) . ?

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
C2 C1 S1 114.4(2) . . ?
C2 C1 Br1 127.3(2) . . ?
S1 C1 Br1 118.31(17) . . ?
C1 C2 C3 111.1(3) . . ?
C4 C3 C2 113.2(3) . . ?
C3 C4 C5 127.6(3) . . ?
C3 C4 S1 111.3(2) . . ?
C5 C4 S1 121.0(2) . . ?
C6 C5 C4 127.3(3) . . ?
C6 C5 S2 109.3(2) . . ?
C4 C5 S2 123.3(2) . . ?
N1 C6 C5 122.1(3) . . ?
N1 C6 C7 123.9(3) . . ?
C5 C6 C7 113.9(3) . . ?
C8 C7 N2 129.6(3) . . ?
C8 C7 C6 112.9(3) . . ?
N2 C7 C6 117.5(3) . . ?
C7 C8 C9 132.3(3) . . ?
C7 C8 S2 109.6(2) . . ?
C9 C8 S2 117.5(2) . . ?
C10 C9 C8 129.2(3) . . ?
C10 C9 S3 111.1(2) . . ?
C8 C9 S3 119.7(2) . . ?
C11 C10 C9 109.2(3) . . ?
C12 C11 C10 114.6(3) . . ?
C11 C12 S3 113.3(3) . . ?
N2 C13 C14 110.5(3) . . ?
N3 C15 N2 118.9(3) . . ?
N3 C15 C16 123.6(3) . . ?
N2 C15 C16 117.5(3) . . ?
N1 C16 C15 125.2(3) . . ?
N1 C16 C17 116.7(3) . . ?
C15 C16 C17 118.0(3) . . ?
O1 C17 N4 122.8(3) . . ?
O1 C17 C16 122.7(3) . . ?
N4 C17 C16 114.5(3) . . ?
O2 C18 N3 121.3(3) . . ?
O2 C18 N4 118.2(3) . . ?
N3 C18 N4 120.5(3) . . ?
N4 C19 C20 113.6(3) . . ?
C19 C20 C21 111.4(3) . . ?
C22 C21 C20 115.2(3) . . ?
C21 C22 C23 115.5(3) . . ?
C24 C23 C22 112.7(4) . . ?
C25 C24 C23 114.8(4) . . ?
C16 N1 C6 115.9(3) . . ?
C15 N2 C7 119.6(2) . . ?
C15 N2 C13 118.8(2) . . ?
C7 N2 C13 120.9(2) . . ?
C15 N3 C18 119.5(3) . . ?
C17 N4 C18 123.7(2) . . ?
C17 N4 C19 117.2(3) . . ?
C18 N4 C19 119.1(2) . . ?
C1 S1 C4 89.97(14) . . ?
C5 S2 C8 94.17(15) . . ?
C12 S3 C9 91.72(18) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.96
_refine_diff_density_min         -0.56
_refine_diff_density_rms         0.08
