# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_l12
_database_code_depnum_ccdc_archive 'CCDC 1435784'
_audit_update_record             
;
2015-11-08 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4-(8-(2-chlorophenyl)-6-isopropylthiazolo[5,4-b]thieno[3,2-e]pyridin-2-yl)phenol
_chemical_melting_point          ?
_chemical_formula_moiety         C23H17ClN2OS2
_chemical_formula_sum            'C25 H25 Cl N2 O3 S2'
_chemical_formula_weight         501.04

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

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

_cell_length_a                   8.3113(5)
_cell_length_b                   12.1970(6)
_cell_length_c                   12.7574(7)
_cell_angle_alpha                101.086(4)
_cell_angle_beta                 105.393(5)
_cell_angle_gamma                93.456(5)
_cell_volume                     1215.10(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3767
_cell_measurement_theta_min      3.6520
_cell_measurement_theta_max      66.5350

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.32
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             524
_exptl_absorpt_coefficient_mu    3.243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
'Wed Aug 05 11:56:07 2015' 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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 10.5058
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8606
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0376
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_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         3.68
_diffrn_reflns_theta_max         66.89
_reflns_number_total             4235
_reflns_number_gt                3579
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
'Wed Aug 05 11:56:07 2015' 
;
_computing_cell_refinement       
; 
'Wed Aug 05 11:56:07 2015' 
;
_computing_data_reduction        
; 
'Wed Aug 05 11:56:07 2015' 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0716P)²+1.2163P] 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         4235
_refine_ls_number_parameters     303
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0609
_refine_ls_R_factor_gt           0.0507
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1294
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
S1 S 0.28395(9) -0.01528(6) 0.38817(6) 0.02813(19) Uani 1 1 d . . .
S2 S 0.04193(9) -0.24887(6) 0.64351(7) 0.0358(2) Uani 1 1 d . . .
Cl1 Cl 0.48145(10) 0.09617(7) 0.91738(7) 0.0448(2) Uani 1 1 d . . .
O1 O 0.5649(3) 0.42323(18) 0.21912(18) 0.0378(5) Uani 1 1 d . . .
H1 H 0.5503 0.4880 0.2434 0.057 Uiso 1 1 calc R . .
N2 N 0.3232(3) 0.15738(19) 0.55261(18) 0.0250(5) Uani 1 1 d . . .
N3 N 0.1639(3) -0.13547(19) 0.5148(2) 0.0290(5) Uani 1 1 d . . .
O4 O 0.5019(3) 0.36615(18) 0.70308(18) 0.0383(5) Uani 1 1 d . . .
H4 H 0.4375 0.3102 0.6661 0.057 Uiso 1 1 calc R . .
C5 C 0.2572(3) 0.0656(2) 0.5847(2) 0.0243(6) Uani 1 1 d . . .
C6 C 0.4033(3) 0.2047(2) 0.3933(2) 0.0252(6) Uani 1 1 d . . .
C7 C 0.2282(3) -0.0368(2) 0.5057(2) 0.0257(6) Uani 1 1 d . . .
C8 C 0.2203(3) 0.0681(2) 0.6864(2) 0.0249(6) Uani 1 1 d . . .
C9 C 0.2427(3) 0.1760(2) 0.7692(2) 0.0269(6) Uani 1 1 d . . .
C10 C 0.1539(3) -0.0352(2) 0.6997(2) 0.0272(6) Uani 1 1 d . . .
C11 C 0.4629(3) 0.1650(2) 0.3015(2) 0.0287(6) Uani 1 1 d . . .
H11 H 0.4662 0.0882 0.2787 0.034 Uiso 1 1 calc R . .
C12 C 0.3989(4) 0.3198(2) 0.4254(2) 0.0305(6) Uani 1 1 d . . .
H12 H 0.3599 0.3472 0.4862 0.037 Uiso 1 1 calc R . .
C13 C 0.1289(3) -0.1312(2) 0.6116(2) 0.0281(6) Uani 1 1 d . . .
C14 C 0.1479(4) 0.2623(3) 0.7390(3) 0.0340(7) Uani 1 1 d . . .
H14 H 0.0700 0.2499 0.6692 0.041 Uiso 1 1 calc R . .
C15 C 0.5168(4) 0.2389(3) 0.2445(2) 0.0303(6) Uani 1 1 d . . .
H15 H 0.5566 0.2117 0.1840 0.036 Uiso 1 1 calc R . .
C16 C 0.3425(3) 0.1274(2) 0.4530(2) 0.0250(6) Uani 1 1 d . . .
C17 C 0.5113(4) 0.3538(2) 0.2777(2) 0.0299(6) Uani 1 1 d . . .
C18 C 0.3790(4) 0.3020(3) 0.9477(3) 0.0396(7) Uani 1 1 d . . .
H18 H 0.4565 0.3153 1.0177 0.048 Uiso 1 1 calc R . .
C19 C 0.1004(3) -0.0626(3) 0.7913(3) 0.0314(6) Uani 1 1 d . . .
H19 H 0.1082 -0.0103 0.8565 0.038 Uiso 1 1 calc R . .
C20 C 0.0379(4) -0.1716(3) 0.7730(3) 0.0331(7) Uani 1 1 d . . .
C21 C 0.3571(4) 0.1981(3) 0.8746(2) 0.0331(7) Uani 1 1 d . . .
C22 C 0.1690(4) 0.3652(3) 0.8114(3) 0.0418(8) Uani 1 1 d . . .
H22 H 0.1053 0.4215 0.7903 0.050 Uiso 1 1 calc R . .
C23 C 0.2845(5) 0.3848(3) 0.9152(3) 0.0441(8) Uani 1 1 d . . .
H23 H 0.2984 0.4545 0.9635 0.053 Uiso 1 1 calc R . .
C24 C 0.4515(4) 0.3942(3) 0.3686(2) 0.0328(7) Uani 1 1 d . . .
H24 H 0.4471 0.4710 0.3909 0.039 Uiso 1 1 calc R . .
C25 C -0.0323(4) -0.2328(3) 0.8469(3) 0.0386(7) Uani 1 1 d . . .
H25 H -0.1479 -0.2646 0.8055 0.046 Uiso 1 1 calc R . .
C26 C -0.0381(6) -0.1556(3) 0.9526(3) 0.0571(10) Uani 1 1 d . . .
H26A H 0.0738 -0.1236 0.9955 0.086 Uiso 1 1 calc R . .
H26B H -0.0873 -0.1974 0.9952 0.086 Uiso 1 1 calc R . .
H26C H -0.1047 -0.0965 0.9348 0.086 Uiso 1 1 calc R . .
C27 C 0.0666(6) -0.3298(4) 0.8724(4) 0.0664(12) Uani 1 1 d . . .
H27A H 0.1811 -0.3012 0.9125 0.100 Uiso 1 1 calc R . .
H27B H 0.0635 -0.3804 0.8040 0.100 Uiso 1 1 calc R . .
H27C H 0.0178 -0.3693 0.9169 0.100 Uiso 1 1 calc R . .
C28 C 0.6715(5) 0.3406(4) 0.7208(3) 0.0591(10) Uani 1 1 d . . .
H28A H 0.6794 0.2885 0.6551 0.071 Uiso 1 1 calc R . .
H28B H 0.7436 0.4092 0.7293 0.071 Uiso 1 1 calc R . .
C37 C 0.7320(7) 0.2938(6) 0.8142(5) 0.100(2) Uani 1 1 d . . .
H37A H 0.7496 0.3507 0.8809 0.149 Uiso 1 1 calc R . .
H37B H 0.8363 0.2650 0.8120 0.149 Uiso 1 1 calc R . .
H37C H 0.6513 0.2337 0.8135 0.149 Uiso 1 1 calc R . .
O1W' O 0.9033(17) 0.4593(10) 0.5576(9) 0.186(6) Uiso 0.644(14) 1 d P A 1
O1W O 1.0660(19) 0.4771(12) 0.5586(11) 0.119(7) Uiso 0.356(14) 1 d P . 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
S1 C7 1.743(3) . ?
S1 C16 1.755(3) . ?
S2 C13 1.734(3) . ?
S2 C20 1.747(3) . ?
Cl1 C21 1.740(3) . ?
O1 C17 1.359(3) . ?
O1 H1 0.8200 . ?
N2 C16 1.308(4) . ?
N2 C5 1.393(3) . ?
N3 C7 1.326(4) . ?
N3 C13 1.335(4) . ?
O4 C28 1.431(4) . ?
O4 H4 0.8200 . ?
C5 C8 1.406(4) . ?
C5 C7 1.409(4) . ?
C6 C12 1.390(4) . ?
C6 C11 1.404(4) . ?
C6 C16 1.466(4) . ?
C8 C10 1.403(4) . ?
C8 C9 1.488(4) . ?
C9 C21 1.390(4) . ?
C9 C14 1.404(4) . ?
C10 C13 1.420(4) . ?
C10 C19 1.443(4) . ?
C11 C15 1.385(4) . ?
C11 H11 0.9300 . ?
C12 C24 1.384(4) . ?
C12 H12 0.9300 . ?
C14 C22 1.379(5) . ?
C14 H14 0.9300 . ?
C15 C17 1.391(4) . ?
C15 H15 0.9300 . ?
C17 C24 1.397(4) . ?
C18 C23 1.376(5) . ?
C18 C21 1.392(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.351(4) . ?
C19 H19 0.9300 . ?
C20 C25 1.516(4) . ?
C22 C23 1.381(5) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.503(5) . ?
C25 C27 1.519(5) . ?
C25 H25 0.9800 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 C37 1.407(6) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
O1W O1W 1.81(3) 2_766 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C16 88.82(13) . . ?
C13 S2 C20 91.58(14) . . ?
C17 O1 H1 109.5 . . ?
C16 N2 C5 110.8(2) . . ?
C7 N3 C13 112.8(2) . . ?
C28 O4 H4 109.5 . . ?
N2 C5 C8 125.8(2) . . ?
N2 C5 C7 114.7(2) . . ?
C8 C5 C7 119.5(2) . . ?
C12 C6 C11 118.6(2) . . ?
C12 C6 C16 120.0(2) . . ?
C11 C6 C16 121.3(3) . . ?
N3 C7 C5 126.8(3) . . ?
N3 C7 S1 123.5(2) . . ?
C5 C7 S1 109.7(2) . . ?
C10 C8 C5 115.4(3) . . ?
C10 C8 C9 123.8(2) . . ?
C5 C8 C9 120.6(2) . . ?
C21 C9 C14 117.6(3) . . ?
C21 C9 C8 123.6(3) . . ?
C14 C9 C8 118.7(3) . . ?
C8 C10 C13 118.6(3) . . ?
C8 C10 C19 130.1(3) . . ?
C13 C10 C19 111.2(2) . . ?
C15 C11 C6 120.7(3) . . ?
C15 C11 H11 119.7 . . ?
C6 C11 H11 119.7 . . ?
C24 C12 C6 121.1(3) . . ?
C24 C12 H12 119.4 . . ?
C6 C12 H12 119.4 . . ?
N3 C13 C10 126.9(2) . . ?
N3 C13 S2 121.8(2) . . ?
C10 C13 S2 111.3(2) . . ?
C22 C14 C9 120.8(3) . . ?
C22 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C11 C15 C17 120.0(3) . . ?
C11 C15 H15 120.0 . . ?
C17 C15 H15 120.0 . . ?
N2 C16 C6 124.5(2) . . ?
N2 C16 S1 115.9(2) . . ?
C6 C16 S1 119.6(2) . . ?
O1 C17 C15 118.0(3) . . ?
O1 C17 C24 122.2(3) . . ?
C15 C17 C24 119.8(3) . . ?
C23 C18 C21 119.1(3) . . ?
C23 C18 H18 120.4 . . ?
C21 C18 H18 120.4 . . ?
C20 C19 C10 113.4(3) . . ?
C20 C19 H19 123.3 . . ?
C10 C19 H19 123.3 . . ?
C19 C20 C25 129.7(3) . . ?
C19 C20 S2 112.5(2) . . ?
C25 C20 S2 117.8(2) . . ?
C9 C21 C18 121.7(3) . . ?
C9 C21 Cl1 120.3(2) . . ?
C18 C21 Cl1 117.9(2) . . ?
C14 C22 C23 120.2(3) . . ?
C14 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.5(3) . . ?
C18 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C12 C24 C17 119.8(3) . . ?
C12 C24 H24 120.1 . . ?
C17 C24 H24 120.1 . . ?
C26 C25 C20 112.5(3) . . ?
C26 C25 C27 110.7(3) . . ?
C20 C25 C27 110.7(3) . . ?
C26 C25 H25 107.6 . . ?
C20 C25 H25 107.6 . . ?
C27 C25 H25 107.6 . . ?
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 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C37 C28 O4 114.5(4) . . ?
C37 C28 H28A 108.6 . . ?
O4 C28 H28A 108.6 . . ?
C37 C28 H28B 108.6 . . ?
O4 C28 H28B 108.6 . . ?
H28A C28 H28B 107.6 . . ?
C28 C37 H37A 109.5 . . ?
C28 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C28 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 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
C16 N2 C5 C8 -179.8(2) . . . . ?
C16 N2 C5 C7 0.6(3) . . . . ?
C13 N3 C7 C5 -1.3(4) . . . . ?
C13 N3 C7 S1 -179.11(19) . . . . ?
N2 C5 C7 N3 -178.7(2) . . . . ?
C8 C5 C7 N3 1.7(4) . . . . ?
N2 C5 C7 S1 -0.6(3) . . . . ?
C8 C5 C7 S1 179.8(2) . . . . ?
C16 S1 C7 N3 178.5(2) . . . . ?
C16 S1 C7 C5 0.3(2) . . . . ?
N2 C5 C8 C10 179.7(2) . . . . ?
C7 C5 C8 C10 -0.7(4) . . . . ?
N2 C5 C8 C9 3.1(4) . . . . ?
C7 C5 C8 C9 -177.3(2) . . . . ?
C10 C8 C9 C21 67.5(4) . . . . ?
C5 C8 C9 C21 -116.2(3) . . . . ?
C10 C8 C9 C14 -114.8(3) . . . . ?
C5 C8 C9 C14 61.5(3) . . . . ?
C5 C8 C10 C13 -0.4(4) . . . . ?
C9 C8 C10 C13 176.1(2) . . . . ?
C5 C8 C10 C19 -179.0(3) . . . . ?
C9 C8 C10 C19 -2.5(4) . . . . ?
C12 C6 C11 C15 0.2(4) . . . . ?
C16 C6 C11 C15 178.7(3) . . . . ?
C11 C6 C12 C24 0.1(4) . . . . ?
C16 C6 C12 C24 -178.3(3) . . . . ?
C7 N3 C13 C10 0.0(4) . . . . ?
C7 N3 C13 S2 179.44(19) . . . . ?
C8 C10 C13 N3 0.8(4) . . . . ?
C19 C10 C13 N3 179.7(3) . . . . ?
C8 C10 C13 S2 -178.7(2) . . . . ?
C19 C10 C13 S2 0.2(3) . . . . ?
C20 S2 C13 N3 -179.4(2) . . . . ?
C20 S2 C13 C10 0.1(2) . . . . ?
C21 C9 C14 C22 0.3(4) . . . . ?
C8 C9 C14 C22 -177.5(3) . . . . ?
C6 C11 C15 C17 -0.3(4) . . . . ?
C5 N2 C16 C6 177.6(2) . . . . ?
C5 N2 C16 S1 -0.4(3) . . . . ?
C12 C6 C16 N2 -18.6(4) . . . . ?
C11 C6 C16 N2 163.0(3) . . . . ?
C12 C6 C16 S1 159.3(2) . . . . ?
C11 C6 C16 S1 -19.1(3) . . . . ?
C7 S1 C16 N2 0.0(2) . . . . ?
C7 S1 C16 C6 -178.1(2) . . . . ?
C11 C15 C17 O1 -179.8(3) . . . . ?
C11 C15 C17 C24 0.0(4) . . . . ?
C8 C10 C19 C20 178.2(3) . . . . ?
C13 C10 C19 C20 -0.5(3) . . . . ?
C10 C19 C20 C25 -179.3(3) . . . . ?
C10 C19 C20 S2 0.6(3) . . . . ?
C13 S2 C20 C19 -0.4(2) . . . . ?
C13 S2 C20 C25 179.5(2) . . . . ?
C14 C9 C21 C18 -0.6(4) . . . . ?
C8 C9 C21 C18 177.2(3) . . . . ?
C14 C9 C21 Cl1 -179.0(2) . . . . ?
C8 C9 C21 Cl1 -1.3(4) . . . . ?
C23 C18 C21 C9 0.3(5) . . . . ?
C23 C18 C21 Cl1 178.8(2) . . . . ?
C9 C14 C22 C23 0.1(5) . . . . ?
C21 C18 C23 C22 0.1(5) . . . . ?
C14 C22 C23 C18 -0.3(5) . . . . ?
C6 C12 C24 C17 -0.4(5) . . . . ?
O1 C17 C24 C12 -179.8(3) . . . . ?
C15 C17 C24 C12 0.3(4) . . . . ?
C19 C20 C25 C26 3.3(5) . . . . ?
S2 C20 C25 C26 -176.6(2) . . . . ?
C19 C20 C25 C27 -121.1(4) . . . . ?
S2 C20 C25 C27 59.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O4 0.82 1.90 2.716(3) 175.4 2_666
O4 H4 N2 0.82 2.12 2.920(3) 165.2 .
C18 H18 O1 0.93 2.54 3.388(4) 151.0 1_556
C24 H24 O4 0.93 2.58 3.257(4) 130.2 2_666
C37 H37C Cl1 0.96 2.85 3.734(6) 153.5 .

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        66.89
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.998
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.069
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/EtOH'
####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1435785'
_audit_update_record             
;
2015-11-08 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
-(8-(2-chlorophenyl)-6-isopropylthiazolo[5,4-b]thieno[3,2-e]pyridin-2-yl)phenol
_chemical_name_common            DF1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H17 Cl N2 O S2'
_chemical_formula_weight         436.97

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.1702(4)
_cell_length_b                   18.4101(9)
_cell_length_c                   24.3386(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4108.9(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6402
_cell_measurement_theta_min      2.7600
_cell_measurement_theta_max      29.0980

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.407
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.90900
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
'Wed Jan 14 09:10:31 2015' 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10.5058
_diffrn_reflns_number            17973
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_av_R_equivalents  0.0339
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         29.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5086
_reflns_number_gt                3919
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0854P)²+7.4822P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5086
_refine_ls_number_parameters     274
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1821
_refine_ls_wR_factor_gt          0.1646
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.46264(9) 0.07954(5) 0.64991(3) 0.0351(2) Uani 1 1 d . . . . .
Cl1 Cl 0.48891(10) 0.30313(4) 0.50650(4) 0.0438(2) Uani 1 1 d . . . . .
N1 N 0.6344(3) 0.03743(12) 0.56652(10) 0.0273(5) Uani 1 1 d . . . . .
S2 S 0.81400(8) 0.00143(4) 0.48252(3) 0.0303(2) Uani 1 1 d . . . . .
N2 N 0.6652(3) 0.09429(12) 0.42475(9) 0.0250(5) Uani 1 1 d . . . . .
C3 C 0.5250(3) 0.07940(15) 0.58254(11) 0.0254(6) Uani 1 1 d . . . . .
C4 C 0.4839(3) 0.13598(15) 0.49366(11) 0.0232(5) Uani 1 1 d . . . . .
C5 C 0.4468(3) 0.12960(15) 0.54944(11) 0.0247(5) Uani 1 1 d . . . . .
C6 C 0.6699(3) 0.04629(14) 0.51424(11) 0.0240(5) Uani 1 1 d . . . . .
C7 C 0.6020(3) 0.09367(14) 0.47630(11) 0.0232(5) Uani 1 1 d . . . . .
C8 C 0.7776(3) 0.05046(15) 0.42243(12) 0.0268(6) Uani 1 1 d . . . . .
O9 O 0.7142(3) 0.12082(15) 0.32024(11) 0.0527(7) Uani 1 1 d . . . . .
H9O H 0.671(5) 0.122(3) 0.3474(19) 0.059(14) Uiso 1 1 d . . . . .
C10 C 0.8706(3) 0.04332(17) 0.37446(13) 0.0328(7) Uani 1 1 d . . . . .
C11 C 0.3330(3) 0.1467(2) 0.63457(12) 0.0385(7) Uani 1 1 d . . . . .
C12 C 0.3363(3) 0.16607(19) 0.58109(12) 0.0338(7) Uani 1 1 d . . . . .
H12A H 0.2726 0.2000 0.5660 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3986(3) 0.18072(16) 0.45440(11) 0.0283(6) Uani 1 1 d . . . . .
C14 C 0.8357(4) 0.07961(18) 0.32554(14) 0.0384(7) Uani 1 1 d . . . . .
C15 C 0.3204(3) 0.14492(19) 0.41220(12) 0.0361(7) Uani 1 1 d . . . . .
H15A H 0.3281 0.0948 0.4085 0.043 Uiso 1 1 calc R U . . .
C16 C 0.3888(4) 0.25555(17) 0.45731(12) 0.0347(7) Uani 1 1 d . . . . .
C17 C 0.3017(4) 0.29434(19) 0.42078(14) 0.0465(9) Uani 1 1 d . . . . .
H17A H 0.2963 0.3447 0.4234 0.056 Uiso 1 1 calc R U . . .
C18 C 0.2326(4) 0.1838(2) 0.37643(14) 0.0463(9) Uani 1 1 d . . . . .
H18A H 0.1798 0.1596 0.3495 0.056 Uiso 1 1 calc R U . . .
C19 C 0.9267(4) 0.0730(2) 0.27976(15) 0.0478(9) Uani 1 1 d . . . . .
H19A H 0.9034 0.0967 0.2472 0.057 Uiso 1 1 calc R U . . .
C20 C 0.2235(5) 0.2584(2) 0.38077(14) 0.0515(10) Uani 1 1 d . . . . .
H20A H 0.1645 0.2844 0.3567 0.062 Uiso 1 1 calc R U . . .
C21 C 1.0877(4) -0.0054(3) 0.33118(16) 0.0598(12) Uani 1 1 d . . . . .
H21A H 1.1716 -0.0337 0.3330 0.072 Uiso 1 1 calc R U . . .
C23 C 1.0516(4) 0.0311(3) 0.28303(16) 0.0544(11) Uani 1 1 d . . . . .
H23A H 1.1124 0.0273 0.2526 0.065 Uiso 1 1 calc R U . . .
C24 C 0.9978(4) 0.0009(2) 0.37606(15) 0.0497(10) Uani 1 1 d . . . . .
H24A H 1.0218 -0.0235 0.4083 0.060 Uiso 1 1 calc R U . . .
C22 C 0.2409(15) 0.1765(16) 0.6813(5) 0.0679(19) Uani 0.644(5) 1 d D . P A 1
H22A H 0.2954 0.2191 0.6940 0.081 Uiso 0.644(5) 1 calc R U P A 1
C25 C 0.1042(7) 0.2071(4) 0.6596(2) 0.0582(11) Uani 0.644(5) 1 d D . P A 1
H25A H 0.0479 0.2269 0.6893 0.087 Uiso 0.644(5) 1 calc R U P A 1
H25B H 0.0493 0.1695 0.6417 0.087 Uiso 0.644(5) 1 calc R U P A 1
H25C H 0.1262 0.2448 0.6336 0.087 Uiso 0.644(5) 1 calc R U P A 1
C26 C 0.2286(8) 0.1325(4) 0.7291(2) 0.0582(11) Uani 0.644(5) 1 d . . P A 1
H26A H 0.1693 0.1569 0.7558 0.087 Uiso 0.644(5) 1 calc R U P A 1
H26B H 0.3239 0.1239 0.7441 0.087 Uiso 0.644(5) 1 calc R U P A 1
H26C H 0.1844 0.0869 0.7195 0.087 Uiso 0.644(5) 1 calc R U P A 1
C22' C 0.242(3) 0.181(3) 0.6776(11) 0.0679(19) Uani 0.356(5) 1 d D . P A 2
H22B H 0.1977 0.2228 0.6597 0.081 Uiso 0.356(5) 1 calc R U P A 2
C25' C 0.1203(13) 0.1401(7) 0.7000(4) 0.0582(11) Uani 0.356(5) 1 d D . P A 2
H25D H 0.0876 0.1629 0.7333 0.087 Uiso 0.356(5) 1 calc R U P A 2
H25E H 0.1504 0.0913 0.7077 0.087 Uiso 0.356(5) 1 calc R U P A 2
H25F H 0.0420 0.1395 0.6738 0.087 Uiso 0.356(5) 1 calc R U P A 2
C26' C 0.3242(13) 0.2111(8) 0.7238(4) 0.0582(11) Uani 0.356(5) 1 d D . P A 2
H26D H 0.2575 0.2292 0.7509 0.087 Uiso 0.356(5) 1 calc R U P A 2
H26E H 0.3847 0.2501 0.7109 0.087 Uiso 0.356(5) 1 calc R U P A 2
H26F H 0.3843 0.1740 0.7398 0.087 Uiso 0.356(5) 1 calc R U 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
S1 C3 1.737(3) . ?
S1 C11 1.756(4) . ?
Cl1 C16 1.745(3) . ?
N1 C6 1.323(4) . ?
N1 C3 1.325(4) . ?
S2 C6 1.739(3) . ?
S2 C8 1.751(3) . ?
N2 C8 1.310(4) . ?
N2 C7 1.382(3) . ?
C3 C5 1.421(4) . ?
C4 C7 1.399(4) . ?
C4 C5 1.405(4) . ?
C4 C13 1.484(4) . ?
C5 C12 1.439(4) . ?
C6 C7 1.415(4) . ?
C8 C10 1.451(4) . ?
O9 C14 1.354(4) . ?
O9 H9O 0.77(5) . ?
C10 C14 1.402(5) . ?
C10 C24 1.405(5) . ?
C11 C12 1.350(4) . ?
C11 C22' 1.48(3) . ?
C11 C22 1.519(16) . ?
C12 H12A 0.9300 . ?
C13 C16 1.382(4) . ?
C13 C15 1.415(4) . ?
C14 C19 1.397(5) . ?
C15 C18 1.385(4) . ?
C15 H15A 0.9300 . ?
C16 C17 1.392(5) . ?
C17 C20 1.379(5) . ?
C17 H17A 0.9300 . ?
C18 C20 1.380(5) . ?
C18 H18A 0.9300 . ?
C19 C23 1.383(6) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 C24 1.373(5) . ?
C21 C23 1.391(6) . ?
C21 H21A 0.9300 . ?
C23 H23A 0.9300 . ?
C24 H24A 0.9300 . ?
C22 C26 1.42(2) . ?
C22 C25 1.47(2) . ?
C22 H22A 0.9800 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C22' C25' 1.45(2) . ?
C22' C26' 1.463(19) . ?
C22' H22B 0.9800 . ?
C25' H25D 0.9600 . ?
C25' H25E 0.9600 . ?
C25' H25F 0.9600 . ?
C26' H26D 0.9600 . ?
C26' H26E 0.9600 . ?
C26' H26F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 S1 C11 91.33(14) . . ?
C6 N1 C3 113.4(2) . . ?
C6 S2 C8 88.93(13) . . ?
C8 N2 C7 111.3(2) . . ?
N1 C3 C5 126.5(3) . . ?
N1 C3 S1 121.9(2) . . ?
C5 C3 S1 111.6(2) . . ?
C7 C4 C5 115.6(2) . . ?
C7 C4 C13 121.5(2) . . ?
C5 C4 C13 122.7(2) . . ?
C4 C5 C3 118.7(3) . . ?
C4 C5 C12 130.5(3) . . ?
C3 C5 C12 110.8(2) . . ?
N1 C6 C7 126.6(3) . . ?
N1 C6 S2 123.7(2) . . ?
C7 C6 S2 109.7(2) . . ?
N2 C7 C4 126.4(2) . . ?
N2 C7 C6 114.4(2) . . ?
C4 C7 C6 119.1(2) . . ?
N2 C8 C10 123.5(3) . . ?
N2 C8 S2 115.5(2) . . ?
C10 C8 S2 120.9(2) . . ?
C14 O9 H9O 111(3) . . ?
C14 C10 C24 118.5(3) . . ?
C14 C10 C8 120.4(3) . . ?
C24 C10 C8 121.1(3) . . ?
C12 C11 C22' 126(2) . . ?
C12 C11 C22 129.8(11) . . ?
C12 C11 S1 112.1(2) . . ?
C22' C11 S1 122(2) . . ?
C22 C11 S1 118.1(10) . . ?
C11 C12 C5 114.1(3) . . ?
C11 C12 H12A 122.9 . . ?
C5 C12 H12A 122.9 . . ?
C16 C13 C15 117.9(3) . . ?
C16 C13 C4 123.7(3) . . ?
C15 C13 C4 118.4(3) . . ?
O9 C14 C19 117.7(3) . . ?
O9 C14 C10 122.4(3) . . ?
C19 C14 C10 120.0(3) . . ?
C18 C15 C13 120.7(3) . . ?
C18 C15 H15A 119.7 . . ?
C13 C15 H15A 119.7 . . ?
C13 C16 C17 121.0(3) . . ?
C13 C16 Cl1 120.1(2) . . ?
C17 C16 Cl1 118.9(3) . . ?
C20 C17 C16 120.2(3) . . ?
C20 C17 H17A 119.9 . . ?
C16 C17 H17A 119.9 . . ?
C20 C18 C15 120.1(3) . . ?
C20 C18 H18A 120.0 . . ?
C15 C18 H18A 120.0 . . ?
C23 C19 C14 119.8(4) . . ?
C23 C19 H19A 120.1 . . ?
C14 C19 H19A 120.1 . . ?
C17 C20 C18 120.0(3) . . ?
C17 C20 H20A 120.0 . . ?
C18 C20 H20A 120.0 . . ?
C24 C21 C23 119.1(4) . . ?
C24 C21 H21A 120.4 . . ?
C23 C21 H21A 120.4 . . ?
C19 C23 C21 121.0(3) . . ?
C19 C23 H23A 119.5 . . ?
C21 C23 H23A 119.5 . . ?
C21 C24 C10 121.5(4) . . ?
C21 C24 H24A 119.2 . . ?
C10 C24 H24A 119.2 . . ?
C26 C22 C25 116.4(10) . . ?
C26 C22 C11 117(2) . . ?
C25 C22 C11 110.0(9) . . ?
C26 C22 H22A 103.9 . . ?
C25 C22 H22A 103.9 . . ?
C11 C22 H22A 103.9 . . ?
C22 C25 H25A 109.5 . . ?
C22 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C22 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C22 C26 H26A 109.5 . . ?
C22 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C22 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25' C22' C26' 107.8(18) . . ?
C25' C22' C11 119(3) . . ?
C26' C22' C11 115(2) . . ?
C25' C22' H22B 104.7 . . ?
C26' C22' H22B 104.7 . . ?
C11 C22' H22B 104.7 . . ?
C22' C25' H25D 109.5 . . ?
C22' C25' H25E 109.5 . . ?
H25D C25' H25E 109.5 . . ?
C22' C25' H25F 109.5 . . ?
H25D C25' H25F 109.5 . . ?
H25E C25' H25F 109.5 . . ?
C22' C26' H26D 109.5 . . ?
C22' C26' H26E 109.5 . . ?
H26D C26' H26E 109.5 . . ?
C22' C26' H26F 109.5 . . ?
H26D C26' H26F 109.5 . . ?
H26E C26' H26F 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
C6 N1 C3 C5 0.7(4) . . . . ?
C6 N1 C3 S1 -178.0(2) . . . . ?
C11 S1 C3 N1 178.5(2) . . . . ?
C11 S1 C3 C5 -0.4(2) . . . . ?
C7 C4 C5 C3 -3.0(4) . . . . ?
C13 C4 C5 C3 173.2(3) . . . . ?
C7 C4 C5 C12 177.9(3) . . . . ?
C13 C4 C5 C12 -5.9(5) . . . . ?
N1 C3 C5 C4 1.4(4) . . . . ?
S1 C3 C5 C4 -179.9(2) . . . . ?
N1 C3 C5 C12 -179.4(3) . . . . ?
S1 C3 C5 C12 -0.6(3) . . . . ?
C3 N1 C6 C7 -1.0(4) . . . . ?
C3 N1 C6 S2 177.2(2) . . . . ?
C8 S2 C6 N1 -176.7(2) . . . . ?
C8 S2 C6 C7 1.7(2) . . . . ?
C8 N2 C7 C4 177.4(3) . . . . ?
C8 N2 C7 C6 -0.7(3) . . . . ?
C5 C4 C7 N2 -175.2(3) . . . . ?
C13 C4 C7 N2 8.6(4) . . . . ?
C5 C4 C7 C6 2.8(4) . . . . ?
C13 C4 C7 C6 -173.4(3) . . . . ?
N1 C6 C7 N2 177.4(3) . . . . ?
S2 C6 C7 N2 -1.0(3) . . . . ?
N1 C6 C7 C4 -0.8(4) . . . . ?
S2 C6 C7 C4 -179.2(2) . . . . ?
C7 N2 C8 C10 -176.1(2) . . . . ?
C7 N2 C8 S2 2.1(3) . . . . ?
C6 S2 C8 N2 -2.3(2) . . . . ?
C6 S2 C8 C10 176.0(2) . . . . ?
N2 C8 C10 C14 -5.5(4) . . . . ?
S2 C8 C10 C14 176.3(2) . . . . ?
N2 C8 C10 C24 173.7(3) . . . . ?
S2 C8 C10 C24 -4.5(4) . . . . ?
C3 S1 C11 C12 1.3(3) . . . . ?
C3 S1 C11 C22' -174.0(12) . . . . ?
C3 S1 C11 C22 -176.2(7) . . . . ?
C22' C11 C12 C5 173.2(10) . . . . ?
C22 C11 C12 C5 175.2(8) . . . . ?
S1 C11 C12 C5 -1.9(4) . . . . ?
C4 C5 C12 C11 -179.2(3) . . . . ?
C3 C5 C12 C11 1.6(4) . . . . ?
C7 C4 C13 C16 -117.8(3) . . . . ?
C5 C4 C13 C16 66.3(4) . . . . ?
C7 C4 C13 C15 63.5(4) . . . . ?
C5 C4 C13 C15 -112.4(3) . . . . ?
C24 C10 C14 O9 179.1(3) . . . . ?
C8 C10 C14 O9 -1.7(5) . . . . ?
C24 C10 C14 C19 0.1(5) . . . . ?
C8 C10 C14 C19 179.3(3) . . . . ?
C16 C13 C15 C18 -2.4(5) . . . . ?
C4 C13 C15 C18 176.3(3) . . . . ?
C15 C13 C16 C17 1.7(5) . . . . ?
C4 C13 C16 C17 -177.1(3) . . . . ?
C15 C13 C16 Cl1 -177.2(2) . . . . ?
C4 C13 C16 Cl1 4.1(4) . . . . ?
C13 C16 C17 C20 -0.1(5) . . . . ?
Cl1 C16 C17 C20 178.8(3) . . . . ?
C13 C15 C18 C20 1.7(5) . . . . ?
O9 C14 C19 C23 -179.6(3) . . . . ?
C10 C14 C19 C23 -0.5(5) . . . . ?
C16 C17 C20 C18 -0.7(6) . . . . ?
C15 C18 C20 C17 0.0(6) . . . . ?
C14 C19 C23 C21 0.6(6) . . . . ?
C24 C21 C23 C19 -0.4(6) . . . . ?
C23 C21 C24 C10 -0.1(6) . . . . ?
C14 C10 C24 C21 0.2(5) . . . . ?
C8 C10 C24 C21 -179.0(4) . . . . ?
C12 C11 C22 C26 161.9(6) . . . . ?
S1 C11 C22 C26 -21.1(10) . . . . ?
C12 C11 C22 C25 26.4(18) . . . . ?
S1 C11 C22 C25 -156.7(11) . . . . ?
C12 C11 C22' C25' 109(4) . . . . ?
S1 C11 C22' C25' -76(3) . . . . ?
C12 C11 C22' C26' -121(3) . . . . ?
S1 C11 C22' C26' 53(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O9 H9O N2 0.77(5) 1.95(5) 2.629(3) 146(5) .
C17 H17A N1 0.93 2.64 3.470(4) 148.8 4_456

_refine_diff_density_max         1.201
_refine_diff_density_min         -0.911
_refine_diff_density_rms         0.082



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3/hexane'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1435786'
_audit_update_record             
;
2015-11-08 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
4-(8-(2-chlorophenyl)-6-isopropylthiazolo[5,4-b]thieno[3,2-e]pyridin-2-yl)-3-hydroxybenzonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H16 Cl N3 O S2'
_chemical_formula_weight         461.97

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   14.1636(4)
_cell_length_b                   7.6109(2)
_cell_length_c                   20.6614(5)
_cell_angle_alpha                90
_cell_angle_beta                 103.485(3)
_cell_angle_gamma                90
_cell_volume                     2165.85(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2766
_cell_measurement_theta_min      3.1940
_cell_measurement_theta_max      60.7690

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    3.541
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.83370
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
'Tue Sep 22 17:41:35 2015' 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_reflns_number            7154
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.209
_diffrn_reflns_theta_max         61.084
_diffrn_reflns_theta_full        61.084
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             3271
_reflns_number_gt                2703
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0724P)²+0.6132P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3271
_refine_ls_number_parameters     294
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1325
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77992(9) -0.00785(12) -0.24097(5) 0.1087(4) Uani 1 1 d . . . . .
S1 S 0.98547(5) 0.19641(10) 0.05596(3) 0.0660(2) Uani 1 1 d . . . . .
S2 S 0.60067(6) 0.13257(13) -0.04565(4) 0.0819(3) Uani 1 1 d . . . . .
O1 O 1.15299(17) 0.4151(3) -0.09265(11) 0.0917(7) Uani 1 1 d . . . . .
H1A H 1.0924 0.3963 -0.1056 0.110 Uiso 1 1 d R U . . .
N1 N 0.79201(17) 0.1624(3) 0.00631(11) 0.0655(6) Uani 1 1 d . . . . .
N2 N 0.99397(17) 0.2849(3) -0.06410(10) 0.0612(5) Uani 1 1 d . . . . .
N3 N 1.5357(3) 0.4017(5) 0.0888(2) 0.1143(11) Uani 1 1 d . . . . .
C1 C 1.4533(3) 0.3833(5) 0.0712(2) 0.0926(10) Uani 1 1 d . . . . .
C2 C 1.3502(2) 0.3526(4) 0.05114(18) 0.0766(8) Uani 1 1 d . . . . .
C3 C 1.2982(2) 0.4036(4) -0.01161(18) 0.0808(8) Uani 1 1 d . . . . .
H3A H 1.3295 0.4610 -0.0404 0.097 Uiso 1 1 calc R U . . .
C4 C 1.1993(2) 0.3687(4) -0.03127(15) 0.0704(7) Uani 1 1 d . . . . .
C5 C 1.1519(2) 0.2889(3) 0.01393(14) 0.0626(7) Uani 1 1 d . . . . .
C6 C 1.2072(2) 0.2393(4) 0.07642(15) 0.0716(7) Uani 1 1 d . . . . .
H6A H 1.1766 0.1842 0.1062 0.086 Uiso 1 1 calc R U . . .
C7 C 1.3048(2) 0.2692(4) 0.09510(17) 0.0781(8) Uani 1 1 d . . . . .
H7A H 1.3403 0.2340 0.1368 0.094 Uiso 1 1 calc R U . . .
C8 C 1.0478(2) 0.2611(3) -0.00417(13) 0.0604(6) Uani 1 1 d . . . . .
C9 C 0.8780(2) 0.2017(4) -0.00518(13) 0.0614(6) Uani 1 1 d . . . . .
C10 C 0.8972(2) 0.2512(3) -0.06703(12) 0.0598(6) Uani 1 1 d . . . . .
C11 C 0.8209(2) 0.2579(4) -0.12358(12) 0.0609(6) Uani 1 1 d . . . . .
C12 C 0.7285(2) 0.2173(4) -0.11335(13) 0.0651(7) Uani 1 1 d . . . . .
C13 C 0.7202(2) 0.1736(4) -0.04808(14) 0.0661(7) Uani 1 1 d . . . . .
C14 C 0.6359(2) 0.2139(5) -0.15896(15) 0.0768(8) Uani 1 1 d . . . . .
H14A H 0.6274 0.2386 -0.2040 0.092 Uiso 1 1 calc R U . . .
C15 C 0.5617(2) 0.1718(5) -0.13111(16) 0.0851(9) Uani 1 1 d . . . . .
C16 C 0.4545(4) 0.1770(10) -0.1633(3) 0.0855(15) Uani 0.717(6) 1 d . . P A 1
H16A H 0.4430 0.3037 -0.1685 0.103 Uiso 0.717(6) 1 calc R U P A 1
C17 C 0.3902(4) 0.1296(12) -0.1214(4) 0.127(2) Uani 0.717(6) 1 d . U P A 1
H17A H 0.4111 0.1863 -0.0790 0.191 Uiso 0.717(6) 1 calc R U P A 1
H17B H 0.3914 0.0045 -0.1153 0.191 Uiso 0.717(6) 1 calc R U P A 1
H17C H 0.3254 0.1664 -0.1421 0.191 Uiso 0.717(6) 1 calc R U P A 1
C18 C 0.4316(9) 0.1177(17) -0.2331(6) 0.152(4) Uani 0.717(6) 1 d . U P A 1
H18A H 0.4783 0.1652 -0.2553 0.227 Uiso 0.717(6) 1 calc R U P A 1
H18B H 0.3678 0.1577 -0.2550 0.227 Uiso 0.717(6) 1 calc R U P A 1
H18C H 0.4335 -0.0083 -0.2344 0.227 Uiso 0.717(6) 1 calc R U P A 1
C16' C 0.4583(12) 0.077(3) -0.1625(9) 0.0855(15) Uani 0.283(6) 1 d . . P A 2
H16B H 0.4866 -0.0135 -0.1860 0.103 Uiso 0.283(6) 1 calc R U P A 2
C17' C 0.4126(12) -0.009(3) -0.1465(9) 0.127(2) Uani 0.283(6) 1 d . U P A 2
H17D H 0.3467 0.0288 -0.1626 0.191 Uiso 0.283(6) 1 calc R U P A 2
H17E H 0.4281 -0.0114 -0.0987 0.191 Uiso 0.283(6) 1 calc R U P A 2
H17F H 0.4204 -0.1244 -0.1632 0.191 Uiso 0.283(6) 1 calc R U P A 2
C18' C 0.431(3) 0.210(5) -0.2276(18) 0.152(4) Uani 0.283(6) 1 d . U P A 2
H18D H 0.4701 0.1826 -0.2581 0.227 Uiso 0.283(6) 1 calc R U P A 2
H18E H 0.4421 0.3299 -0.2130 0.227 Uiso 0.283(6) 1 calc R U P A 2
H18F H 0.3633 0.1962 -0.2495 0.227 Uiso 0.283(6) 1 calc R U P A 2
C19 C 0.8378(2) 0.3132(4) -0.18925(13) 0.0637(7) Uani 1 1 d . . . . .
C20 C 0.8754(2) 0.4809(4) -0.19561(15) 0.0780(8) Uani 1 1 d . . . . .
H20A H 0.8915 0.5538 -0.1585 0.094 Uiso 1 1 calc R U . . .
C21 C 0.8890(3) 0.5399(5) -0.25607(18) 0.0888(10) Uani 1 1 d . . . . .
H21A H 0.9144 0.6514 -0.2593 0.107 Uiso 1 1 calc R U . . .
C22 C 0.8653(3) 0.4346(5) -0.31116(17) 0.0903(10) Uani 1 1 d . . . . .
H22A H 0.8723 0.4766 -0.3520 0.108 Uiso 1 1 calc R U . . .
C23 C 0.8312(3) 0.2678(5) -0.30647(16) 0.0902(10) Uani 1 1 d . . . . .
H23A H 0.8165 0.1954 -0.3438 0.108 Uiso 1 1 calc R U . . .
C24 C 0.8187(2) 0.2076(4) -0.24553(14) 0.0732(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C24 1.739(3) . ?
S1 C9 1.737(3) . ?
S1 C8 1.754(3) . ?
S2 C13 1.734(3) . ?
S2 C15 1.748(3) . ?
O1 C4 1.333(4) . ?
O1 H1A 0.8499 . ?
N1 C9 1.328(4) . ?
N1 C13 1.331(4) . ?
N2 C8 1.307(3) . ?
N2 C10 1.382(4) . ?
N3 C1 1.147(5) . ?
C1 C2 1.442(5) . ?
C2 C7 1.383(5) . ?
C2 C3 1.389(5) . ?
C3 C4 1.390(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.409(4) . ?
C5 C6 1.397(4) . ?
C5 C8 1.450(4) . ?
C6 C7 1.365(4) . ?
C6 H6A 0.9300 . ?
C7 H7A 0.9300 . ?
C9 C10 1.418(4) . ?
C10 C11 1.395(4) . ?
C11 C12 1.409(4) . ?
C11 C19 1.492(4) . ?
C12 C13 1.420(4) . ?
C12 C14 1.425(4) . ?
C14 C15 1.349(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.509(6) . ?
C15 C16' 1.627(18) . ?
C16 C17 1.440(9) . ?
C16 C18 1.473(12) . ?
C16 H16A 0.9800 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C16' C17' 1.03(2) . ?
C16' C18' 1.66(5) . ?
C16' H16B 0.9800 . ?
C17' H17D 0.9600 . ?
C17' H17E 0.9600 . ?
C17' H17F 0.9600 . ?
C18' H18D 0.9600 . ?
C18' H18E 0.9600 . ?
C18' H18F 0.9600 . ?
C19 C24 1.387(4) . ?
C19 C20 1.401(4) . ?
C20 C21 1.383(4) . ?
C20 H20A 0.9300 . ?
C21 C22 1.368(5) . ?
C21 H21A 0.9300 . ?
C22 C23 1.370(5) . ?
C22 H22A 0.9300 . ?
C23 C24 1.389(4) . ?
C23 H23A 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
C9 S1 C8 88.80(13) . . ?
C13 S2 C15 91.16(15) . . ?
C4 O1 H1A 119.5 . . ?
C9 N1 C13 112.7(2) . . ?
C8 N2 C10 111.7(2) . . ?
N3 C1 C2 177.2(5) . . ?
C7 C2 C3 121.0(3) . . ?
C7 C2 C1 118.7(3) . . ?
C3 C2 C1 120.3(3) . . ?
C2 C3 C4 119.9(3) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
O1 C4 C3 117.8(3) . . ?
O1 C4 C5 122.7(3) . . ?
C3 C4 C5 119.5(3) . . ?
C6 C5 C4 118.6(3) . . ?
C6 C5 C8 121.1(3) . . ?
C4 C5 C8 120.4(3) . . ?
C7 C6 C5 121.9(3) . . ?
C7 C6 H6A 119.0 . . ?
C5 C6 H6A 119.0 . . ?
C6 C7 C2 119.1(3) . . ?
C6 C7 H7A 120.5 . . ?
C2 C7 H7A 120.5 . . ?
N2 C8 C5 123.9(2) . . ?
N2 C8 S1 115.5(2) . . ?
C5 C8 S1 120.5(2) . . ?
N1 C9 C10 126.7(3) . . ?
N1 C9 S1 123.3(2) . . ?
C10 C9 S1 110.0(2) . . ?
N2 C10 C11 126.6(2) . . ?
N2 C10 C9 114.0(2) . . ?
C11 C10 C9 119.4(3) . . ?
C10 C11 C12 115.6(2) . . ?
C10 C11 C19 121.0(2) . . ?
C12 C11 C19 123.3(2) . . ?
C11 C12 C13 118.6(3) . . ?
C11 C12 C14 130.4(3) . . ?
C13 C12 C14 110.9(3) . . ?
N1 C13 C12 126.9(3) . . ?
N1 C13 S2 121.5(2) . . ?
C12 C13 S2 111.5(2) . . ?
C15 C14 C12 114.2(3) . . ?
C15 C14 H14A 122.9 . . ?
C12 C14 H14A 122.9 . . ?
C14 C15 C16 127.5(4) . . ?
C14 C15 C16' 130.9(7) . . ?
C14 C15 S2 112.2(3) . . ?
C16 C15 S2 119.8(3) . . ?
C16' C15 S2 111.7(7) . . ?
C17 C16 C18 119.0(7) . . ?
C17 C16 C15 116.2(5) . . ?
C18 C16 C15 113.1(6) . . ?
C17 C16 H16A 101.5 . . ?
C18 C16 H16A 101.5 . . ?
C15 C16 H16A 101.5 . . ?
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 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17' C16' C15 137.0(18) . . ?
C17' C16' C18' 127(2) . . ?
C15 C16' C18' 94.1(16) . . ?
C17' C16' H16B 94.3 . . ?
C15 C16' H16B 94.3 . . ?
C18' C16' H16B 94.3 . . ?
C16' C17' H17D 109.5 . . ?
C16' C17' H17E 109.5 . . ?
H17D C17' H17E 109.5 . . ?
C16' C17' H17F 109.5 . . ?
H17D C17' H17F 109.5 . . ?
H17E C17' H17F 109.5 . . ?
C16' C18' H18D 109.5 . . ?
C16' C18' H18E 109.5 . . ?
H18D C18' H18E 109.5 . . ?
C16' C18' H18F 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
C24 C19 C20 116.9(3) . . ?
C24 C19 C11 123.9(3) . . ?
C20 C19 C11 119.2(2) . . ?
C21 C20 C19 121.1(3) . . ?
C21 C20 H20A 119.4 . . ?
C19 C20 H20A 119.4 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22A 119.8 . . ?
C23 C22 H22A 119.8 . . ?
C22 C23 C24 119.4(3) . . ?
C22 C23 H23A 120.3 . . ?
C24 C23 H23A 120.3 . . ?
C19 C24 C23 121.9(3) . . ?
C19 C24 Cl1 120.2(2) . . ?
C23 C24 Cl1 117.9(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
C7 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C4 178.1(3) . . . . ?
C2 C3 C4 O1 -178.0(3) . . . . ?
C2 C3 C4 C5 2.9(5) . . . . ?
O1 C4 C5 C6 177.8(3) . . . . ?
C3 C4 C5 C6 -3.1(4) . . . . ?
O1 C4 C5 C8 -2.8(4) . . . . ?
C3 C4 C5 C8 176.3(3) . . . . ?
C4 C5 C6 C7 1.4(4) . . . . ?
C8 C5 C6 C7 -178.0(3) . . . . ?
C5 C6 C7 C2 0.6(5) . . . . ?
C3 C2 C7 C6 -0.9(5) . . . . ?
C1 C2 C7 C6 -179.9(3) . . . . ?
C10 N2 C8 C5 -179.1(2) . . . . ?
C10 N2 C8 S1 -0.6(3) . . . . ?
C6 C5 C8 N2 -171.4(3) . . . . ?
C4 C5 C8 N2 9.2(4) . . . . ?
C6 C5 C8 S1 10.1(4) . . . . ?
C4 C5 C8 S1 -169.3(2) . . . . ?
C9 S1 C8 N2 0.1(2) . . . . ?
C9 S1 C8 C5 178.7(2) . . . . ?
C13 N1 C9 C10 0.0(4) . . . . ?
C13 N1 C9 S1 -179.3(2) . . . . ?
C8 S1 C9 N1 179.7(2) . . . . ?
C8 S1 C9 C10 0.4(2) . . . . ?
C8 N2 C10 C11 -177.6(3) . . . . ?
C8 N2 C10 C9 0.9(3) . . . . ?
N1 C9 C10 N2 179.9(2) . . . . ?
S1 C9 C10 N2 -0.8(3) . . . . ?
N1 C9 C10 C11 -1.5(4) . . . . ?
S1 C9 C10 C11 177.9(2) . . . . ?
N2 C10 C11 C12 179.8(2) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
N2 C10 C11 C19 -3.0(4) . . . . ?
C9 C10 C11 C19 178.6(2) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C19 C11 C12 C13 -177.2(3) . . . . ?
C10 C11 C12 C14 178.9(3) . . . . ?
C19 C11 C12 C14 1.8(5) . . . . ?
C9 N1 C13 C12 1.6(4) . . . . ?
C9 N1 C13 S2 -178.8(2) . . . . ?
C11 C12 C13 N1 -1.6(5) . . . . ?
C14 C12 C13 N1 179.2(3) . . . . ?
C11 C12 C13 S2 178.8(2) . . . . ?
C14 C12 C13 S2 -0.4(3) . . . . ?
C15 S2 C13 N1 -179.3(3) . . . . ?
C15 S2 C13 C12 0.4(2) . . . . ?
C11 C12 C14 C15 -178.8(3) . . . . ?
C13 C12 C14 C15 0.3(4) . . . . ?
C12 C14 C15 C16 172.3(5) . . . . ?
C12 C14 C15 C16' -151.7(9) . . . . ?
C12 C14 C15 S2 0.0(4) . . . . ?
C13 S2 C15 C14 -0.2(3) . . . . ?
C13 S2 C15 C16 -173.2(4) . . . . ?
C13 S2 C15 C16' 157.1(7) . . . . ?
C14 C15 C16 C17 -178.3(5) . . . . ?
S2 C15 C16 C17 -6.5(8) . . . . ?
C14 C15 C16 C18 38.8(10) . . . . ?
S2 C15 C16 C18 -149.4(8) . . . . ?
C14 C15 C16' C17' 145(3) . . . . ?
S2 C15 C16' C17' -7(3) . . . . ?
C14 C15 C16' C18' -50.7(18) . . . . ?
S2 C15 C16' C18' 157.5(14) . . . . ?
C10 C11 C19 C24 119.9(3) . . . . ?
C12 C11 C19 C24 -63.1(4) . . . . ?
C10 C11 C19 C20 -59.8(4) . . . . ?
C12 C11 C19 C20 117.2(3) . . . . ?
C24 C19 C20 C21 2.5(5) . . . . ?
C11 C19 C20 C21 -177.8(3) . . . . ?
C19 C20 C21 C22 0.4(5) . . . . ?
C20 C21 C22 C23 -2.4(6) . . . . ?
C21 C22 C23 C24 1.5(6) . . . . ?
C20 C19 C24 C23 -3.4(5) . . . . ?
C11 C19 C24 C23 176.9(3) . . . . ?
C20 C19 C24 Cl1 175.5(2) . . . . ?
C11 C19 C24 Cl1 -4.2(4) . . . . ?
C22 C23 C24 C19 1.5(5) . . . . ?
C22 C23 C24 Cl1 -177.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A N2 0.85 1.99 2.650(3) 134.0 .
C3 H3A N3 0.93 2.57 3.468(5) 161.2 3_865
C23 H23A O1 0.93 2.59 3.438(4) 151.0 2_744

_refine_diff_density_max         0.485
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.041



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/EtOH'
####################################################################### 
# 
# 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_added_by_encifer
_database_code_depnum_ccdc_archive 'CCDC 1435787'
_audit_update_record             
;
2015-11-08 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
N-(2-(8-(2-chlorophenyl)-6-isopropylthiazolo[5,4-b]thieno[3,2-e]pyridin-2-yl)phenyl)methanesulfonamide
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 Cl N3 O2 S3'
_chemical_formula_weight         514.07

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   9.5948(6)
_cell_length_b                   10.3128(7)
_cell_length_c                   12.0188(8)
_cell_angle_alpha                87.285(5)
_cell_angle_beta                 86.081(5)
_cell_angle_gamma                83.966(5)
_cell_volume                     1178.93(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(10)
_cell_measurement_reflns_used    2482
_cell_measurement_theta_min      3.6460
_cell_measurement_theta_max      60.7250

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_F_000             532
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    4.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.13818
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_reflns_number            6797
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_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         3.689
_diffrn_reflns_theta_max         61.136
_diffrn_reflns_theta_full        61.136
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_reflns_number_total             3550
_reflns_number_gt                2945
_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       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0884P)²+1.2481P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3550
_refine_ls_number_parameters     266
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0651
_refine_ls_wR_factor_ref         0.1820
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
S1 S 0.62413(12) 0.91565(10) 0.10679(10) 0.0637(3) Uani 1 1 d . . . . .
S2 S 0.32555(11) 0.58225(10) -0.08658(9) 0.0595(3) Uani 1 1 d . . . . .
S3 S 0.12374(13) 0.18389(11) 0.24852(10) 0.0681(4) Uani 1 1 d . . . . .
N1 N 0.4746(4) 0.7526(3) 0.0072(3) 0.0567(8) Uani 1 1 d . . . . .
N2 N 0.0889(4) 0.3116(3) 0.1649(3) 0.0641(9) Uani 1 1 d . . . . .
H2D H 0.0057 0.3509 0.1910 0.077 Uiso 1 1 d R U . . .
O1 O 0.0237(4) 0.0944(4) 0.2408(4) 0.0953(12) Uani 1 1 d . . . . .
O2 O 0.1381(6) 0.2367(4) 0.3537(3) 0.1133(15) Uani 1 1 d . . . . .
C1 C 0.7322(9) 0.9409(7) 0.4253(6) 0.118(3) Uani 1 1 d . . . . .
H1A H 0.7674 0.8503 0.4251 0.177 Uiso 1 1 calc R U . . .
H1B H 0.8000 0.9899 0.4550 0.177 Uiso 1 1 calc R U . . .
H1C H 0.6459 0.9512 0.4708 0.177 Uiso 1 1 calc R U . . .
C2 C 0.6512(8) 1.1307(6) 0.3016(7) 0.115(2) Uani 1 1 d . . . . .
H2A H 0.6370 1.1557 0.2249 0.172 Uiso 1 1 calc R U . . .
H2B H 0.5636 1.1442 0.3451 0.172 Uiso 1 1 calc R U . . .
H2C H 0.7176 1.1828 0.3292 0.172 Uiso 1 1 calc R U . . .
C3 C 0.7068(5) 0.9890(5) 0.3104(5) 0.0749(13) Uani 1 1 d . . . . .
H3A H 0.7988 0.9820 0.2691 0.090 Uiso 1 1 calc R U . . .
C4 C 0.6170(4) 0.9054(4) 0.2515(4) 0.0612(11) Uani 1 1 d . . . . .
C5 C 0.5294(4) 0.8185(4) 0.2946(4) 0.0589(10) Uani 1 1 d . . . . .
H5A H 0.5126 0.8025 0.3709 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4651(4) 0.7536(4) 0.2116(3) 0.0509(9) Uani 1 1 d . . . . .
C7 C 0.3708(4) 0.6584(4) 0.2237(3) 0.0518(9) Uani 1 1 d . . . . .
C8 C 0.3342(4) 0.6093(4) 0.1249(3) 0.0473(9) Uani 1 1 d . . . . .
N9 N 0.2461(3) 0.5126(3) 0.1166(3) 0.0514(8) Uani 1 1 d . . . . .
C10 C 0.2319(4) 0.4881(4) 0.0125(3) 0.0502(9) Uani 1 1 d . . . . .
C11 C 0.1475(4) 0.3907(4) -0.0254(3) 0.0530(10) Uani 1 1 d . . . . .
C12 C 0.0799(4) 0.3035(4) 0.0482(4) 0.0560(10) Uani 1 1 d . . . . .
C13 C 0.0010(5) 0.2131(4) 0.0054(5) 0.0679(12) Uani 1 1 d . . . . .
H13A H -0.0454 0.1562 0.0536 0.081 Uiso 1 1 calc R U . . .
C14 C -0.0081(5) 0.2080(5) -0.1081(5) 0.0750(14) Uani 1 1 d . . . . .
H14A H -0.0586 0.1458 -0.1358 0.090 Uiso 1 1 calc R U . . .
C15 C 0.0554(5) 0.2923(5) -0.1805(5) 0.0735(13) Uani 1 1 d . . . . .
H15A H 0.0473 0.2887 -0.2570 0.088 Uiso 1 1 calc R U . . .
C16 C 0.1323(5) 0.3835(5) -0.1392(4) 0.0665(11) Uani 1 1 d . . . . .
H16A H 0.1750 0.4415 -0.1888 0.080 Uiso 1 1 calc R U . . .
C17 C 0.3877(4) 0.6598(4) 0.0223(3) 0.0512(9) Uani 1 1 d . . . . .
C18 C 0.5107(4) 0.7959(4) 0.1031(4) 0.0538(10) Uani 1 1 d . . . . .
C19 C 0.2845(6) 0.1109(7) 0.1982(6) 0.111(2) Uani 1 1 d . . . . .
H19A H 0.3547 0.1700 0.2025 0.167 Uiso 1 1 calc R U . . .
H19B H 0.3092 0.0328 0.2422 0.167 Uiso 1 1 calc R U . . .
H19C H 0.2790 0.0894 0.1219 0.167 Uiso 1 1 calc R U . . .
Cl1 Cl 0.1669(3) 0.8163(2) 0.3762(2) 0.0850(6) Uani 0.549(2) 1 d D . P A 1
C20 C 0.3275(8) 0.5944(6) 0.3321(4) 0.0795(9) Uani 0.549(2) 1 d G . P A 1
C21 C 0.3843(7) 0.4679(6) 0.3581(4) 0.0795(9) Uani 0.549(2) 1 d G . P A 1
H21A H 0.4472 0.4235 0.3073 0.095 Uiso 0.549(2) 1 calc R U P A 1
C22 C 0.3471(7) 0.4077(5) 0.4602(5) 0.0795(9) Uani 0.549(2) 1 d G . P A 1
H22A H 0.3851 0.3231 0.4776 0.095 Uiso 0.549(2) 1 calc R U P A 1
C23 C 0.2531(7) 0.4740(5) 0.5362(4) 0.0795(9) Uani 0.549(2) 1 d G . P A 1
H23A H 0.2282 0.4337 0.6045 0.095 Uiso 0.549(2) 1 calc R U P A 1
C24 C 0.1962(6) 0.6005(5) 0.5101(4) 0.0795(9) Uani 0.549(2) 1 d G . P A 1
H24A H 0.1333 0.6448 0.5610 0.095 Uiso 0.549(2) 1 calc R U P A 1
C25 C 0.2334(7) 0.6607(5) 0.4080(5) 0.0795(9) Uani 0.549(2) 1 d DG . P A 1
Cl1' Cl 0.4451(3) 0.4011(3) 0.3462(3) 0.0850(6) Uani 0.451(2) 1 d D . P A 2
C20' C 0.2947(9) 0.6348(7) 0.3396(5) 0.0795(9) Uani 0.451(2) 1 d G . P A 2
C21' C 0.1966(9) 0.7307(6) 0.3839(6) 0.0795(9) Uani 0.451(2) 1 d G . P A 2
H21B H 0.1820 0.8116 0.3467 0.095 Uiso 0.451(2) 1 calc R U P A 2
C22' C 0.1204(8) 0.7056(6) 0.4837(6) 0.0795(9) Uani 0.451(2) 1 d G . P A 2
H22B H 0.0548 0.7697 0.5134 0.095 Uiso 0.451(2) 1 calc R U P A 2
C23' C 0.1422(8) 0.5846(7) 0.5393(5) 0.0795(9) Uani 0.451(2) 1 d G . P A 2
H23B H 0.0912 0.5678 0.6061 0.095 Uiso 0.451(2) 1 calc R U P A 2
C24' C 0.2403(8) 0.4887(6) 0.4950(5) 0.0795(9) Uani 0.451(2) 1 d G . P A 2
H24B H 0.2549 0.4077 0.5322 0.095 Uiso 0.451(2) 1 calc R U P A 2
C25' C 0.3165(8) 0.5138(7) 0.3952(6) 0.0795(9) Uani 0.451(2) 1 d DG . 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
S1 C18 1.734(4) . ?
S1 C4 1.734(5) . ?
S2 C17 1.736(4) . ?
S2 C10 1.760(4) . ?
S3 O1 1.411(4) . ?
S3 O2 1.421(4) . ?
S3 N2 1.638(4) . ?
S3 C19 1.727(6) . ?
N1 C17 1.332(5) . ?
N1 C18 1.336(6) . ?
N2 C12 1.418(6) . ?
C1 C3 1.473(8) . ?
C2 C3 1.503(8) . ?
C3 C4 1.512(6) . ?
C4 C5 1.353(6) . ?
C5 C6 1.435(6) . ?
C6 C7 1.400(5) . ?
C6 C18 1.411(6) . ?
C7 C8 1.393(6) . ?
C7 C20 1.486(5) . ?
C7 C20' 1.549(6) . ?
C8 N9 1.385(5) . ?
C8 C17 1.401(6) . ?
N9 C10 1.306(5) . ?
C10 C11 1.462(6) . ?
C11 C16 1.391(6) . ?
C11 C12 1.407(6) . ?
C12 C13 1.398(6) . ?
C13 C14 1.376(7) . ?
C14 C15 1.361(8) . ?
C15 C16 1.384(7) . ?
Cl1 C25 1.700(5) . ?
C20 C21 1.3900 . ?
C20 C25 1.3900 . ?
C21 C22 1.3900 . ?
C22 C23 1.3900 . ?
C23 C24 1.3900 . ?
C24 C25 1.3900 . ?
Cl1' C25' 1.698(6) . ?
C20' C21' 1.3900 . ?
C20' C25' 1.3900 . ?
C21' C22' 1.3900 . ?
C22' C23' 1.3900 . ?
C23' C24' 1.3900 . ?
C24' C25' 1.3900 . ?

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
C18 S1 C4 91.6(2) . . ?
C17 S2 C10 88.81(18) . . ?
O1 S3 O2 118.7(3) . . ?
O1 S3 N2 110.1(2) . . ?
O2 S3 N2 104.5(2) . . ?
O1 S3 C19 107.8(3) . . ?
O2 S3 C19 109.5(4) . . ?
N2 S3 C19 105.4(3) . . ?
C17 N1 C18 112.8(3) . . ?
C12 N2 S3 123.3(3) . . ?
C1 C3 C2 113.7(6) . . ?
C1 C3 C4 113.0(4) . . ?
C2 C3 C4 111.2(4) . . ?
C5 C4 C3 129.6(5) . . ?
C5 C4 S1 112.3(3) . . ?
C3 C4 S1 118.0(3) . . ?
C4 C5 C6 113.7(4) . . ?
C7 C6 C18 118.8(4) . . ?
C7 C6 C5 130.2(4) . . ?
C18 C6 C5 111.0(4) . . ?
C8 C7 C6 115.8(4) . . ?
C8 C7 C20 119.2(4) . . ?
C6 C7 C20 124.2(4) . . ?
C8 C7 C20' 124.4(5) . . ?
C6 C7 C20' 118.7(5) . . ?
N9 C8 C7 125.9(3) . . ?
N9 C8 C17 114.6(3) . . ?
C7 C8 C17 119.5(3) . . ?
C10 N9 C8 111.5(3) . . ?
N9 C10 C11 125.5(4) . . ?
N9 C10 S2 115.1(3) . . ?
C11 C10 S2 119.4(3) . . ?
C16 C11 C12 118.1(4) . . ?
C16 C11 C10 119.0(4) . . ?
C12 C11 C10 122.9(4) . . ?
C13 C12 C11 119.5(4) . . ?
C13 C12 N2 120.9(4) . . ?
C11 C12 N2 119.5(4) . . ?
C14 C13 C12 120.0(5) . . ?
C15 C14 C13 121.3(4) . . ?
C14 C15 C16 119.2(5) . . ?
C15 C16 C11 121.8(5) . . ?
N1 C17 C8 126.5(4) . . ?
N1 C17 S2 123.4(3) . . ?
C8 C17 S2 110.0(3) . . ?
N1 C18 C6 126.5(4) . . ?
N1 C18 S1 122.1(3) . . ?
C6 C18 S1 111.4(3) . . ?
C21 C20 C25 120.0 . . ?
C21 C20 C7 119.3(4) . . ?
C25 C20 C7 120.7(4) . . ?
C20 C21 C22 120.0 . . ?
C23 C22 C21 120.0 . . ?
C24 C23 C22 120.0 . . ?
C23 C24 C25 120.0 . . ?
C24 C25 C20 120.0 . . ?
C24 C25 Cl1 120.4(3) . . ?
C20 C25 Cl1 119.6(3) . . ?
C21' C20' C25' 120.0 . . ?
C21' C20' C7 120.1(5) . . ?
C25' C20' C7 119.7(5) . . ?
C20' C21' C22' 120.0 . . ?
C23' C22' C21' 120.0 . . ?
C22' C23' C24' 120.0 . . ?
C25' C24' C23' 120.0 . . ?
C24' C25' C20' 120.0 . . ?
C24' C25' Cl1' 120.0(4) . . ?
C20' C25' Cl1' 119.8(4) . . ?

_refine_diff_density_max         0.591
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.062



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: THF/EtOH'
####################################################################### 
# 
# 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_DF5
_database_code_depnum_ccdc_archive 'CCDC 1435788'
_audit_update_record             
;
2015-11-08 deposited with the CCDC.
2016-03-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
'N-(2-(8-(2-chlorophenyl)-6-isopropylthiazolo[5,4-b]thieno [3,2-e]pyridin-2-yl)phenyl)-4-methylbenzenesulfonamide'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H24 Cl N3 O2 S3'
_chemical_formula_weight         590.15

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

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

_cell_length_a                   10.6742(5)
_cell_length_b                   10.9730(6)
_cell_length_c                   13.2942(7)
_cell_angle_alpha                112.061(5)
_cell_angle_beta                 95.450(4)
_cell_angle_gamma                93.025(4)
_cell_volume                     1429.98(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2819
_cell_measurement_theta_min      3.5990
_cell_measurement_theta_max      60.9370

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             612
_exptl_absorpt_coefficient_mu    3.495
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64262
_exptl_absorpt_correction_T_max  1.00000
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 16.0855
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8252
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.62
_diffrn_reflns_theta_max         61.00
_reflns_number_total             4301
_reflns_number_gt                3505
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies,Version 1.17'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies,Version 1.17'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies,Version 1.17'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker 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)+(0.0941P)²+0.6016P] 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         4301
_refine_ls_number_parameters     356
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0680
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1711
_refine_ls_wR_factor_gt          0.1593
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
S1 S 0.21721(9) 0.42418(10) 0.40073(7) 0.0779(3) Uani 1 1 d . . .
S2 S 0.58405(10) 0.16550(10) 0.51904(9) 0.0857(3) Uani 1 1 d . . .
S3 S 0.16775(9) 0.94846(10) 0.77774(9) 0.0867(3) Uani 1 1 d . . .
Cl4 Cl 0.35046(13) 0.43093(18) 0.85558(12) 0.1302(5) Uani 1 1 d . . .
N1 N 0.2726(2) 0.6012(3) 0.5978(2) 0.0654(7) Uani 1 1 d . . .
C2 C 0.4404(3) 0.4995(3) 0.6722(3) 0.0635(8) Uani 1 1 d . . .
N3 N 0.4006(3) 0.2921(3) 0.4571(2) 0.0747(8) Uani 1 1 d . . .
N4 N 0.1864(3) 0.8436(3) 0.6563(3) 0.0796(8) Uani 1 1 d . . .
H4 H 0.2615 0.8211 0.6463 0.18(3) Uiso 1 1 calc R . .
C5 C 0.0920(3) 0.7861(4) 0.5659(3) 0.0728(9) Uani 1 1 d . . .
C6 C 0.3373(3) 0.3982(3) 0.4865(3) 0.0673(8) Uani 1 1 d . . .
C7 C 0.3526(3) 0.5031(3) 0.5883(3) 0.0626(8) Uani 1 1 d . . .
O8 O 0.1017(3) 1.0534(3) 0.7683(3) 0.1119(10) Uani 1 1 d . . .
C9 C 0.1969(3) 0.5727(4) 0.5070(3) 0.0676(8) Uani 1 1 d . . .
C10 C 0.5107(3) 0.3893(3) 0.6441(3) 0.0669(8) Uani 1 1 d . . .
C11 C 0.4865(3) 0.2918(3) 0.5368(3) 0.0711(9) Uani 1 1 d . . .
O12 O 0.2912(3) 0.9764(3) 0.8366(3) 0.1060(9) Uani 1 1 d . . .
C13 C 0.0992(3) 0.6559(4) 0.4913(3) 0.0722(9) Uani 1 1 d . . .
C14 C 0.6092(3) 0.3572(4) 0.7081(3) 0.0755(9) Uani 1 1 d . . .
H14 H 0.6379 0.4103 0.7806 0.091 Uiso 1 1 calc R . .
C15 C 0.4573(3) 0.6032(4) 0.7829(3) 0.0736(9) Uani 1 1 d . . .
C16 C 0.6568(4) 0.2416(4) 0.6528(3) 0.0803(10) Uani 1 1 d . . .
C17 C 0.0092(3) 0.6035(5) 0.3990(3) 0.0849(11) Uani 1 1 d . . .
H17 H 0.0129 0.5179 0.3491 0.102 Uiso 1 1 calc R . .
C18 C -0.0044(4) 0.8571(5) 0.5442(4) 0.0894(11) Uani 1 1 d . . .
H18 H -0.0094 0.9433 0.5924 0.107 Uiso 1 1 calc R . .
C19 C 0.0735(4) 0.8612(4) 0.8337(3) 0.0802(10) Uani 1 1 d . . .
C20 C -0.0459(4) 0.8959(5) 0.8593(4) 0.1010(13) Uani 1 1 d . . .
H20 H -0.0783 0.9654 0.8449 0.121 Uiso 1 1 calc R . .
C21 C 0.4230(4) 0.5804(5) 0.8720(3) 0.0948(13) Uani 1 1 d . . .
C22 C 0.1192(5) 0.7583(5) 0.8565(4) 0.1040(14) Uani 1 1 d . . .
H22 H 0.1998 0.7348 0.8415 0.125 Uiso 1 1 calc R . .
C23 C 0.5149(4) 0.7349(4) 0.7971(4) 0.1146(19) Uani 1 1 d . . .
H23 H 0.5374 0.7545 0.7386 0.137 Uiso 1 1 calc R . .
C24 C -0.0854(4) 0.6767(6) 0.3803(4) 0.0982(14) Uani 1 1 d . . .
H24 H -0.1444 0.6406 0.3181 0.118 Uiso 1 1 calc R . .
C25 C 0.7592(4) 0.1737(4) 0.6914(4) 0.0979(12) Uani 1 1 d . . .
H25 H 0.8178 0.1494 0.6361 0.117 Uiso 1 1 calc R . .
C26 C 0.8346(5) 0.2620(5) 0.7977(5) 0.1175(16) Uani 1 1 d . . .
H26A H 0.8674 0.3416 0.7914 0.176 Uiso 1 1 calc R . .
H26B H 0.9035 0.2172 0.8147 0.176 Uiso 1 1 calc R . .
H26C H 0.7812 0.2835 0.8550 0.176 Uiso 1 1 calc R . .
C27 C -0.0916(4) 0.8024(6) 0.4536(4) 0.1001(14) Uani 1 1 d . . .
H27 H -0.1560 0.8511 0.4416 0.120 Uiso 1 1 calc R . .
C28 C -0.0724(5) 0.7253(5) 0.9275(4) 0.1003(13) Uani 1 1 d . . .
C29 C 0.5002(6) 0.8003(8) 0.9893(5) 0.126(2) Uani 1 1 d . . .
H29 H 0.5161 0.8666 1.0588 0.152 Uiso 1 1 calc R . .
C30 C 0.0466(6) 0.6909(5) 0.9008(4) 0.1138(16) Uani 1 1 d . . .
H30 H 0.0778 0.6198 0.9136 0.137 Uiso 1 1 calc R . .
C31 C 0.5330(5) 0.8272(5) 0.9036(5) 0.1140(17) Uani 1 1 d . . .
H31 H 0.5694 0.9115 0.9167 0.137 Uiso 1 1 calc R . .
C32 C 0.4447(5) 0.6804(9) 0.9788(4) 0.126(2) Uani 1 1 d . . .
H32 H 0.4221 0.6649 1.0391 0.151 Uiso 1 1 calc R . .
C33 C -0.1157(5) 0.8284(6) 0.9054(5) 0.1124(15) Uani 1 1 d . . .
H33 H -0.1954 0.8534 0.9224 0.135 Uiso 1 1 calc R . .
C34 C -0.1500(7) 0.6535(6) 0.9811(5) 0.143(2) Uani 1 1 d . . .
H34A H -0.2275 0.6934 0.9964 0.214 Uiso 1 1 calc R . .
H34B H -0.1031 0.6588 1.0482 0.214 Uiso 1 1 calc R . .
H34C H -0.1686 0.5624 0.9329 0.214 Uiso 1 1 calc R . .
C35 C 0.7037(6) 0.0469(6) 0.6966(7) 0.163(3) Uani 1 1 d . . .
H35A H 0.6452 0.0668 0.7499 0.244 Uiso 1 1 calc R . .
H35B H 0.7703 0.0020 0.7169 0.244 Uiso 1 1 calc R . .
H35C H 0.6602 -0.0088 0.6262 0.244 Uiso 1 1 calc R . .


_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 C6 1.740(3) . ?
S1 C9 1.751(4) . ?
S2 C11 1.736(4) . ?
S2 C16 1.736(4) . ?
S3 O8 1.420(3) . ?
S3 O12 1.423(3) . ?
S3 N4 1.631(3) . ?
S3 C19 1.749(4) . ?
Cl4 C21 1.703(6) . ?
N1 C9 1.309(4) . ?
N1 C7 1.386(4) . ?
C2 C7 1.400(4) . ?
C2 C10 1.405(5) . ?
C2 C15 1.471(5) . ?
N3 C6 1.326(4) . ?
N3 C11 1.335(5) . ?
N4 C5 1.411(5) . ?
C5 C18 1.395(5) . ?
C5 C13 1.411(6) . ?
C6 C7 1.397(5) . ?
C9 C13 1.471(5) . ?
C10 C11 1.415(5) . ?
C10 C14 1.432(5) . ?
C13 C17 1.396(5) . ?
C14 C16 1.358(5) . ?
C15 C21 1.377(6) . ?
C15 C23 1.477(7) . ?
C16 C25 1.511(5) . ?
C17 C24 1.384(6) . ?
C18 C27 1.365(7) . ?
C19 C22 1.375(6) . ?
C19 C20 1.385(6) . ?
C20 C33 1.359(7) . ?
C21 C32 1.418(8) . ?
C22 C30 1.359(7) . ?
C23 C31 1.385(7) . ?
C24 C27 1.367(7) . ?
C25 C26 1.502(7) . ?
C25 C35 1.512(8) . ?
C28 C33 1.363(7) . ?
C28 C30 1.385(7) . ?
C28 C34 1.511(8) . ?
C29 C31 1.351(9) . ?
C29 C32 1.366(9) . ?

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
C6 S1 C9 88.89(16) . . ?
C11 S2 C16 91.59(17) . . ?
O8 S3 O12 119.7(2) . . ?
O8 S3 N4 109.63(19) . . ?
O12 S3 N4 104.13(17) . . ?
O8 S3 C19 108.5(2) . . ?
O12 S3 C19 108.2(2) . . ?
N4 S3 C19 105.85(18) . . ?
C9 N1 C7 110.9(3) . . ?
C7 C2 C10 115.6(3) . . ?
C7 C2 C15 122.4(3) . . ?
C10 C2 C15 122.0(3) . . ?
C6 N3 C11 113.1(3) . . ?
C5 N4 S3 126.8(3) . . ?
C18 C5 N4 121.8(4) . . ?
C18 C5 C13 118.7(4) . . ?
N4 C5 C13 119.4(3) . . ?
N3 C6 C7 126.8(3) . . ?
N3 C6 S1 123.5(3) . . ?
C7 C6 S1 109.7(2) . . ?
N1 C7 C6 115.0(3) . . ?
N1 C7 C2 125.5(3) . . ?
C6 C7 C2 119.4(3) . . ?
N1 C9 C13 124.2(3) . . ?
N1 C9 S1 115.5(3) . . ?
C13 C9 S1 120.3(3) . . ?
C2 C10 C11 118.6(3) . . ?
C2 C10 C14 130.0(3) . . ?
C11 C10 C14 111.4(3) . . ?
N3 C11 C10 126.4(3) . . ?
N3 C11 S2 122.4(3) . . ?
C10 C11 S2 111.2(3) . . ?
C17 C13 C5 118.5(3) . . ?
C17 C13 C9 118.6(4) . . ?
C5 C13 C9 122.9(3) . . ?
C16 C14 C10 113.5(4) . . ?
C21 C15 C2 122.2(4) . . ?
C21 C15 C23 119.9(4) . . ?
C2 C15 C23 117.8(4) . . ?
C14 C16 C25 129.5(4) . . ?
C14 C16 S2 112.4(3) . . ?
C25 C16 S2 118.1(3) . . ?
C24 C17 C13 121.2(4) . . ?
C27 C18 C5 121.2(4) . . ?
C22 C19 C20 118.6(4) . . ?
C22 C19 S3 119.9(3) . . ?
C20 C19 S3 121.5(3) . . ?
C33 C20 C19 120.1(5) . . ?
C15 C21 C32 121.3(5) . . ?
C15 C21 Cl4 120.2(4) . . ?
C32 C21 Cl4 118.5(4) . . ?
C30 C22 C19 120.1(4) . . ?
C31 C23 C15 115.4(6) . . ?
C27 C24 C17 119.6(4) . . ?
C26 C25 C16 112.9(4) . . ?
C26 C25 C35 112.0(5) . . ?
C16 C25 C35 110.3(4) . . ?
C18 C27 C24 120.7(4) . . ?
C33 C28 C30 117.3(5) . . ?
C33 C28 C34 121.3(5) . . ?
C30 C28 C34 121.3(5) . . ?
C31 C29 C32 123.2(6) . . ?
C22 C30 C28 121.8(5) . . ?
C29 C31 C23 122.9(6) . . ?
C29 C32 C21 117.3(5) . . ?
C20 C33 C28 122.0(4) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        61.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.964
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.049
