# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_wdh1061
_database_code_depnum_ccdc_archive 'CCDC 2076357'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-02-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N3 O S'
_chemical_formula_sum            'C26 H21 N3 O S'
_chemical_formula_weight         423.52
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H21 N3 O1 S1'
_chemical_oxdiff_usercomment     'RV-34-c t9'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.6611(3)
_cell_length_b                   13.0943(3)
_cell_length_c                   10.2975(3)
_cell_angle_alpha                90
_cell_angle_beta                 110.729(3)
_cell_angle_gamma                90
_cell_volume                     1092.25(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    21119
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.0520
_cell_measurement_theta_min      2.6430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             444
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_unetI/netI     0.0212
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            36101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.514
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00  53.00   1.00    1.50    --  -17.00  77.00-180.00  100
  2  ω    -47.00  53.00   1.00    1.50    --  -17.00  77.00 150.00  100
  3  ω    -11.00  89.00   1.00    1.50    --   19.03  77.00 -60.00  100
  4  ω    -11.00  89.00   1.00    1.50    --   19.03  77.00  60.00  100
  5  ω    -11.00  89.00   1.00    1.50    --   19.03  77.00-180.00  100
  6  ω    -93.00 -35.00   1.00    1.50    --  -17.00-178.00-180.00   58
  7  ω    -67.00   8.00   1.00    1.50    --  -17.00 113.00  84.00   75
  8  ω    -38.00  52.00   1.00    1.50    --  -17.00  57.00 -60.00   90
  9  ω    -42.00  55.00   1.00    1.50    --  -17.00  38.00  90.00   97
 10  ω    -94.00 -34.00   1.00    1.50    --  -17.00 178.00 -90.00   60
 11  ω    -50.00  40.00   1.00    1.50    --   19.03 -57.00 -60.00   90
 12  ω    -20.00  61.00   1.00    1.50    --   19.03 -99.00 -90.00   81
 13  ω    -20.00  61.00   1.00    1.50    --   19.03 -99.00  60.00   81
 14  ω    -54.00  92.00   1.00    1.50    --   19.03   0.00-180.00  146
 15  ω    -54.00  92.00   1.00    1.50    --   19.03   0.00-150.00  146
 16  ω    -54.00  92.00   1.00    1.50    --   19.03   0.00-120.00  146
 17  ω     -8.00  69.00   1.00    1.50    --   19.03-113.00  -6.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0334565000
_diffrn_orient_matrix_UB_12      -0.0414578000
_diffrn_orient_matrix_UB_13      0.0456607000
_diffrn_orient_matrix_UB_21      -0.0186114000
_diffrn_orient_matrix_UB_22      -0.0334875000
_diffrn_orient_matrix_UB_23      -0.0576573000
_diffrn_orient_matrix_UB_31      0.0787603000
_diffrn_orient_matrix_UB_32      0.0096740000
_diffrn_orient_matrix_UB_33      -0.0040060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4345
_reflns_number_total             4474
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2021 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.046(19)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     285
_refine_ls_number_reflns         4474
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+0.3057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0626
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C 0.9903(2) 0.65338(15) 0.7547(2) 0.0127(4) Uani 1 1 d . . . . .
C2 C 0.9336(2) 0.65405(15) 0.86980(19) 0.0133(4) Uani 1 1 d . . . . .
C3 C 0.9224(2) 0.56463(16) 0.9431(2) 0.0166(4) Uani 1 1 d . . . . .
H3 H 0.9547 0.5008 0.9169 0.020 Uiso 1 1 calc R . . . .
C4 C 0.8652(3) 0.56882(17) 1.0518(2) 0.0198(4) Uani 1 1 d . . . . .
H4 H 0.8588 0.5080 1.0998 0.024 Uiso 1 1 calc R . . . .
C5 C 0.8161(3) 0.66226(18) 1.0925(2) 0.0212(5) Uani 1 1 d . . . . .
H5 H 0.7770 0.6643 1.1678 0.025 Uiso 1 1 calc R . . . .
C6 C 0.8248(3) 0.75003(17) 1.0236(2) 0.0193(4) Uani 1 1 d . . . . .
H6 H 0.7912 0.8129 1.0515 0.023 Uiso 1 1 calc R . . . .
C7 C 0.8832(2) 0.74868(16) 0.9111(2) 0.0152(4) Uani 1 1 d . . . . .
C8 C 0.8909(2) 0.83877(15) 0.8371(2) 0.0171(4) Uani 1 1 d . . . . .
H8 H 0.8571 0.9019 0.8640 0.021 Uiso 1 1 calc R . . . .
C9 C 0.9460(3) 0.83675(15) 0.7283(2) 0.0170(4) Uani 1 1 d . . . . .
H9 H 0.9508 0.8981 0.6806 0.020 Uiso 1 1 calc R . . . .
C10 C 0.9959(2) 0.74335(16) 0.68627(19) 0.0143(4) Uani 1 1 d . . . . .
N11 N 1.1866(2) 0.52550(13) 0.71534(17) 0.0137(3) Uani 1 1 d . . . . .
C12 C 1.0315(2) 0.55749(15) 0.69886(19) 0.0125(4) Uani 1 1 d . . . . .
C13 C 0.9324(2) 0.48610(17) 0.60981(18) 0.0138(4) Uani 1 1 d . . . . .
N14 N 1.0290(2) 0.41634(13) 0.57712(17) 0.0170(4) Uani 1 1 d . . . . .
N15 N 1.1853(2) 0.44027(13) 0.64302(18) 0.0175(4) Uani 1 1 d . . . . .
S16 S 0.71744(6) 0.48580(4) 0.53745(5) 0.01765(12) Uani 1 1 d . . . . .
C17 C 0.6632(2) 0.36603(15) 0.5900(2) 0.0158(4) Uani 1 1 d . . . . .
C18 C 0.4975(3) 0.33848(17) 0.5272(2) 0.0199(4) Uani 1 1 d . . . . .
H18 H 0.4233 0.3815 0.4593 0.024 Uiso 1 1 calc R . . . .
C19 C 0.4423(3) 0.24766(18) 0.5650(2) 0.0248(5) Uani 1 1 d . . . . .
H19 H 0.3297 0.2286 0.5229 0.030 Uiso 1 1 calc R . . . .
C20 C 0.5505(3) 0.18443(18) 0.6639(2) 0.0268(5) Uani 1 1 d . . . . .
H20 H 0.5122 0.1223 0.6893 0.032 Uiso 1 1 calc R . . . .
C21 C 0.7150(3) 0.21242(17) 0.7255(2) 0.0237(5) Uani 1 1 d . . . . .
H21 H 0.7891 0.1691 0.7931 0.028 Uiso 1 1 calc R . . . .
C22 C 0.7719(3) 0.30314(16) 0.6891(2) 0.0197(4) Uani 1 1 d . . . . .
H22 H 0.8845 0.3221 0.7318 0.024 Uiso 1 1 calc R . . . .
C23 C 1.3468(2) 0.57000(16) 0.8034(2) 0.0155(4) Uani 1 1 d . . . . .
H23 H 1.3226 0.6324 0.8489 0.019 Uiso 1 1 calc R . . . .
C24 C 1.4446(3) 0.60364(17) 0.7134(2) 0.0205(4) Uani 1 1 d . . . . .
H24A H 1.5469 0.6371 0.7716 0.031 Uiso 1 1 calc GR . . . .
H24B H 1.3784 0.6516 0.6425 0.031 Uiso 1 1 calc GR . . . .
H24C H 1.4714 0.5438 0.6682 0.031 Uiso 1 1 calc GR . . . .
O25 O 1.04966(18) 0.73904(11) 0.57747(15) 0.0187(3) Uani 1 1 d . . . . .
C26 C 1.4359(2) 0.49432(17) 0.91773(19) 0.0156(4) Uani 1 1 d . . . . .
C27 C 1.5235(3) 0.41165(17) 0.8952(2) 0.0202(4) Uani 1 1 d . . . . .
H27 H 1.5287 0.4006 0.8057 0.024 Uiso 1 1 calc R . . . .
C28 C 1.6038(3) 0.34485(17) 1.0031(2) 0.0236(5) Uani 1 1 d . . . . .
H28 H 1.6642 0.2887 0.9868 0.028 Uiso 1 1 calc R . . . .
C29 C 1.5965(3) 0.35962(17) 1.1340(2) 0.0229(5) Uani 1 1 d . . . . .
H29 H 1.6521 0.3142 1.2076 0.027 Uiso 1 1 calc R . . . .
C30 C 1.5073(3) 0.44124(18) 1.1568(2) 0.0245(5) Uani 1 1 d . . . . .
H30 H 1.5005 0.4512 1.2460 0.029 Uiso 1 1 calc R . . . .
C31 C 1.4278(3) 0.50862(15) 1.0495(2) 0.0207(5) Uani 1 1 d . . . . .
H31 H 1.3676 0.5647 1.0660 0.025 Uiso 1 1 calc R . . . .
H25 H 1.029(3) 0.797(2) 0.536(3) 0.025(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.435(3) . ?
C1 C10 1.382(3) . ?
C1 C12 1.476(3) . ?
C2 C3 1.415(3) . ?
C2 C7 1.428(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.407(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.367(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.418(3) . ?
C7 C8 1.419(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.365(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.415(3) . ?
C10 O25 1.358(2) . ?
N11 C12 1.359(3) . ?
N11 N15 1.340(2) . ?
N11 C23 1.482(2) . ?
C12 C13 1.376(3) . ?
C13 N14 1.359(3) . ?
C13 S16 1.7434(18) . ?
N14 N15 1.319(2) . ?
S16 C17 1.776(2) . ?
C17 C18 1.396(3) . ?
C17 C22 1.388(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(3) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.526(3) . ?
C23 C26 1.523(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.86(3) . ?
C26 C27 1.388(3) . ?
C26 C31 1.396(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.386(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.391(3) . ?
C31 H31 0.9500 . ?

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 C12 121.83(17) . . ?
C10 C1 C2 119.99(18) . . ?
C10 C1 C12 118.01(17) . . ?
C3 C2 C1 122.95(18) . . ?
C3 C2 C7 118.23(17) . . ?
C7 C2 C1 118.81(18) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 C2 120.89(19) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.7(2) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 119.91(19) . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 119.5 . . ?
C5 C6 C7 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C6 C7 C2 119.30(19) . . ?
C6 C7 C8 121.77(19) . . ?
C8 C7 C2 118.92(17) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 C7 121.45(18) . . ?
C9 C8 H8 119.3 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.08(18) . . ?
C10 C9 H9 120.0 . . ?
C1 C10 C9 120.74(17) . . ?
O25 C10 C1 117.98(18) . . ?
O25 C10 C9 121.28(18) . . ?
C12 N11 C23 128.69(17) . . ?
N15 N11 C12 111.97(16) . . ?
N15 N11 C23 119.30(16) . . ?
N11 C12 C1 125.31(17) . . ?
N11 C12 C13 103.25(16) . . ?
C13 C12 C1 131.11(17) . . ?
C12 C13 S16 127.29(16) . . ?
N14 C13 C12 109.17(16) . . ?
N14 C13 S16 123.40(15) . . ?
N15 N14 C13 108.81(16) . . ?
N14 N15 N11 106.80(16) . . ?
C13 S16 C17 103.27(10) . . ?
C18 C17 S16 115.24(15) . . ?
C22 C17 S16 124.35(16) . . ?
C22 C17 C18 120.38(19) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.41(19) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.5(2) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.2 . . ?
C19 C20 C21 119.7(2) . . ?
C21 C20 H20 120.2 . . ?
C20 C21 H21 119.7 . . ?
C20 C21 C22 120.5(2) . . ?
C22 C21 H21 119.7 . . ?
C17 C22 C21 119.5(2) . . ?
C17 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
N11 C23 H23 107.6 . . ?
N11 C23 C24 110.04(16) . . ?
N11 C23 C26 109.01(16) . . ?
C24 C23 H23 107.6 . . ?
C26 C23 H23 107.6 . . ?
C26 C23 C24 114.78(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 O25 H25 107.7(17) . . ?
C27 C26 C23 122.40(18) . . ?
C27 C26 C31 119.06(19) . . ?
C31 C26 C23 118.55(19) . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.37(19) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.4(2) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.2 . . ?
C28 C29 C30 119.5(2) . . ?
C30 C29 H29 120.2 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.2(2) . . ?
C31 C30 H30 119.9 . . ?
C26 C31 H31 119.8 . . ?
C30 C31 C26 120.4(2) . . ?
C30 C31 H31 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 -179.12(19) . . . . ?
C1 C2 C7 C6 179.14(17) . . . . ?
C1 C2 C7 C8 -0.1(3) . . . . ?
C1 C12 C13 N14 173.45(19) . . . . ?
C1 C12 C13 S16 -2.4(3) . . . . ?
C2 C1 C10 C9 -0.1(3) . . . . ?
C2 C1 C10 O25 -179.72(16) . . . . ?
C2 C1 C12 N11 -107.3(2) . . . . ?
C2 C1 C12 C13 80.4(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C2 C7 C8 C9 -0.2(3) . . . . ?
C3 C2 C7 C6 0.3(3) . . . . ?
C3 C2 C7 C8 -178.91(17) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C5 C6 C7 C2 -0.1(3) . . . . ?
C5 C6 C7 C8 179.13(19) . . . . ?
C6 C7 C8 C9 -179.45(19) . . . . ?
C7 C2 C3 C4 -0.3(3) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C9 C10 C1 -0.2(3) . . . . ?
C8 C9 C10 O25 179.37(18) . . . . ?
C10 C1 C2 C3 179.03(19) . . . . ?
C10 C1 C2 C7 0.3(3) . . . . ?
C10 C1 C12 N11 77.4(2) . . . . ?
C10 C1 C12 C13 -94.9(3) . . . . ?
N11 C12 C13 N14 -0.1(2) . . . . ?
N11 C12 C13 S16 -175.99(15) . . . . ?
N11 C23 C26 C27 80.3(2) . . . . ?
N11 C23 C26 C31 -99.2(2) . . . . ?
C12 C1 C2 C3 3.8(3) . . . . ?
C12 C1 C2 C7 -174.94(17) . . . . ?
C12 C1 C10 C9 175.26(17) . . . . ?
C12 C1 C10 O25 -4.3(3) . . . . ?
C12 N11 N15 N14 0.7(2) . . . . ?
C12 N11 C23 C24 -119.2(2) . . . . ?
C12 N11 C23 C26 114.1(2) . . . . ?
C12 C13 N14 N15 0.6(2) . . . . ?
C12 C13 S16 C17 -123.52(18) . . . . ?
C13 N14 N15 N11 -0.8(2) . . . . ?
C13 S16 C17 C18 -170.14(15) . . . . ?
C13 S16 C17 C22 11.8(2) . . . . ?
N14 C13 S16 C17 61.16(18) . . . . ?
N15 N11 C12 C1 -174.44(17) . . . . ?
N15 N11 C12 C13 -0.4(2) . . . . ?
N15 N11 C23 C24 63.3(2) . . . . ?
N15 N11 C23 C26 -63.4(2) . . . . ?
S16 C13 N14 N15 176.63(14) . . . . ?
S16 C17 C18 C19 -177.97(17) . . . . ?
S16 C17 C22 C21 177.98(17) . . . . ?
C17 C18 C19 C20 -0.2(3) . . . . ?
C18 C17 C22 C21 0.1(3) . . . . ?
C18 C19 C20 C21 0.1(4) . . . . ?
C19 C20 C21 C22 0.1(4) . . . . ?
C20 C21 C22 C17 -0.2(3) . . . . ?
C22 C17 C18 C19 0.1(3) . . . . ?
C23 N11 C12 C1 7.9(3) . . . . ?
C23 N11 C12 C13 -178.00(18) . . . . ?
C23 N11 N15 N14 178.61(16) . . . . ?
C23 C26 C27 C28 179.60(19) . . . . ?
C23 C26 C31 C30 179.96(19) . . . . ?
C24 C23 C26 C27 -43.6(3) . . . . ?
C24 C23 C26 C31 136.8(2) . . . . ?
C26 C27 C28 C29 0.4(3) . . . . ?
C27 C26 C31 C30 0.4(3) . . . . ?
C27 C28 C29 C30 0.5(3) . . . . ?
C28 C29 C30 C31 -0.9(3) . . . . ?
C29 C30 C31 C26 0.5(3) . . . . ?
C31 C26 C27 C28 -0.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.116
_oxdiff_exptl_absorpt_empirical_full_min 0.831
####################################################################### 
# 
# 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_wdh1062
_database_code_depnum_ccdc_archive 'CCDC 2076358'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N3 O2 S'
_chemical_formula_sum            'C26 H21 N3 O2 S'
_chemical_formula_weight         439.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C25 H21 N3 O2 S1'
_chemical_oxdiff_usercomment     'RV-34-A t18'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.84610(10)
_cell_length_b                   15.7021(3)
_cell_length_c                   21.1251(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2270.91(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5702
_cell_measurement_temperature    100.03(10)
_cell_measurement_theta_max      28.5660
_cell_measurement_theta_min      3.1210
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11256
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         26.340
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.03(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00   22.50    --  -17.00 -99.00-120.00   45
  2  ω     -2.00  88.00   1.00   22.50    --   19.03  57.00 150.00   90
  3  ω     -2.00  88.00   1.00   22.50    --   19.03  57.00  60.00   90
  4  ω    -93.00 -68.00   1.00   22.50    --  -17.00-178.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0067055000
_diffrn_orient_matrix_UB_12      -0.0424223000
_diffrn_orient_matrix_UB_13      0.0288672000
_diffrn_orient_matrix_UB_21      -0.0326734000
_diffrn_orient_matrix_UB_22      -0.0069873000
_diffrn_orient_matrix_UB_23      0.0184262000
_diffrn_orient_matrix_UB_31      -0.0041342000
_diffrn_orient_matrix_UB_32      -0.0137989000
_diffrn_orient_matrix_UB_33      -0.0977181000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.743
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4267
_reflns_number_total             4637
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Flack x determined using 1671 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     290
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0371
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0336P)²+0.5517P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0831
_refine_ls_wR_factor_ref         0.0865
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O25(H25)
2.b Ternary CH refined with riding coordinates:
 C23(H23)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
S16 S -1.16626(9) 0.92396(4) 0.13067(3) 0.01862(15) Uani 1 1 d . . . . .
O25 O -0.6694(3) 0.86782(13) 0.18145(9) 0.0295(5) Uani 1 1 d . . . . .
H25 H -0.5579 0.8881 0.1743 0.044 Uiso 1 1 d R . . . .
O32 O -1.3672(3) 0.95719(12) 0.14543(9) 0.0254(4) Uani 1 1 d . . . . .
N11 N -1.0331(3) 0.72207(13) 0.22575(10) 0.0207(5) Uani 1 1 d . . . . .
N14 N -1.2175(3) 0.74855(15) 0.14579(10) 0.0248(5) Uani 1 1 d . . . . .
N15 N -1.1522(4) 0.68690(14) 0.18160(10) 0.0260(5) Uani 1 1 d . . . . .
C1 C -0.9097(4) 0.86393(16) 0.26028(12) 0.0175(5) Uani 1 1 d . . . . .
C2 C -0.9838(4) 0.88901(16) 0.32054(12) 0.0187(5) Uani 1 1 d . . . . .
C3 C -1.1714(4) 0.86375(16) 0.34213(12) 0.0220(6) Uani 1 1 d . . . . .
H3 H -1.2506 0.8281 0.3164 0.026 Uiso 1 1 calc R . . . .
C4 C -1.2386(4) 0.8906(2) 0.39982(14) 0.0290(7) Uani 1 1 d . . . . .
H4 H -1.3644 0.8732 0.4137 0.035 Uiso 1 1 calc R . . . .
C5 C -1.1252(5) 0.94344(19) 0.43876(13) 0.0321(7) Uani 1 1 d . . . . .
H5 H -1.1736 0.9614 0.4787 0.039 Uiso 1 1 calc R . . . .
C6 C -0.9442(5) 0.96882(19) 0.41873(14) 0.0294(7) Uani 1 1 d . . . . .
H6 H -0.8675 1.0045 0.4452 0.035 Uiso 1 1 calc R . . . .
C7 C -0.8692(4) 0.94282(16) 0.35928(12) 0.0228(6) Uani 1 1 d . . . . .
C8 C -0.6854(4) 0.97061(18) 0.33631(13) 0.0271(6) Uani 1 1 d . . . . .
H8 H -0.6071 1.0064 0.3622 0.033 Uiso 1 1 calc R . . . .
C9 C -0.6183(4) 0.94749(17) 0.27831(14) 0.0264(6) Uani 1 1 d . . . . .
H9 H -0.4953 0.9677 0.2639 0.032 Uiso 1 1 calc R . . . .
C10 C -0.7312(4) 0.89342(18) 0.23933(13) 0.0217(6) Uani 1 1 d . . . . .
C12 C -1.0229(4) 0.80775(16) 0.21852(12) 0.0184(5) Uani 1 1 d . . . . .
C13 C -1.1396(4) 0.82308(16) 0.16699(12) 0.0191(5) Uani 1 1 d . . . . .
C17 C -1.1706(4) 0.88684(16) 0.05072(12) 0.0231(6) Uani 1 1 d . . . . .
C18 C -0.9952(5) 0.8897(2) 0.01768(14) 0.0342(7) Uani 1 1 d . . . . .
H18 H -0.8816 0.9130 0.0368 0.041 Uiso 1 1 calc R . . . .
C19 C -0.9884(7) 0.8585(2) -0.04289(16) 0.0497(10) Uani 1 1 d . . . . .
H19 H -0.8693 0.8592 -0.0659 0.060 Uiso 1 1 calc R . . . .
C20 C -1.1541(8) 0.8262(2) -0.06999(15) 0.0582(12) Uani 1 1 d . . . . .
H20 H -1.1480 0.8037 -0.1117 0.070 Uiso 1 1 calc R . . . .
C21 C -1.3307(7) 0.8258(2) -0.03793(16) 0.0531(11) Uani 1 1 d . . . . .
H21 H -1.4448 0.8045 -0.0580 0.064 Uiso 1 1 calc R . . . .
C22 C -1.3406(5) 0.85680(18) 0.02429(14) 0.0334(7) Uani 1 1 d . . . . .
H22 H -1.4599 0.8570 0.0472 0.040 Uiso 1 1 calc R . . . .
C23 C -0.9164(4) 0.66965(17) 0.27010(13) 0.0237(6) Uani 1 1 d . . . . .
H23 H -0.7901 0.7001 0.2775 0.028 Uiso 1 1 calc R . . . .
C24 C -0.8684(5) 0.58410(18) 0.24001(14) 0.0342(7) Uani 1 1 d . . . . .
H24A H -0.9887 0.5511 0.2346 0.051 Uiso 1 1 calc GR . . . .
H24B H -0.7781 0.5527 0.2674 0.051 Uiso 1 1 calc GR . . . .
H24C H -0.8073 0.5934 0.1986 0.051 Uiso 1 1 calc GR . . . .
C26 C -1.0164(4) 0.66012(17) 0.33365(13) 0.0253(6) Uani 1 1 d . . . . .
C27 C -1.2019(5) 0.62503(19) 0.33840(15) 0.0338(7) Uani 1 1 d . . . . .
H27 H -1.2693 0.6075 0.3013 0.041 Uiso 1 1 calc R . . . .
C28 C -1.2891(6) 0.6155(2) 0.39736(18) 0.0483(9) Uani 1 1 d . . . . .
H28 H -1.4152 0.5907 0.4007 0.058 Uiso 1 1 calc R . . . .
C29 C -1.1917(7) 0.6425(2) 0.45145(17) 0.0547(11) Uani 1 1 d . . . . .
H29 H -1.2528 0.6375 0.4917 0.066 Uiso 1 1 calc R . . . .
C30 C -1.0066(7) 0.6764(2) 0.44680(16) 0.0507(10) Uani 1 1 d . . . . .
H30 H -0.9386 0.6935 0.4839 0.061 Uiso 1 1 calc R . . . .
C31 C -0.9201(5) 0.6854(2) 0.38816(14) 0.0361(7) Uani 1 1 d . . . . .
H31 H -0.7929 0.7093 0.3852 0.043 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
S16 O32 1.5038(19) . ?
S16 C13 1.770(3) . ?
S16 C17 1.787(3) . ?
O25 H25 0.8402 . ?
O25 C10 1.355(3) . ?
N11 N15 1.356(3) . ?
N11 C12 1.356(3) . ?
N11 C23 1.481(3) . ?
N14 N15 1.307(3) . ?
N14 C13 1.362(3) . ?
C1 C2 1.426(4) . ?
C1 C10 1.380(4) . ?
C1 C12 1.468(3) . ?
C2 C3 1.419(4) . ?
C2 C7 1.414(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.369(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.403(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.368(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.417(4) . ?
C7 C8 1.418(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.358(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.413(4) . ?
C12 C13 1.372(4) . ?
C17 C18 1.389(4) . ?
C17 C22 1.374(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.367(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.404(4) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.522(4) . ?
C23 C26 1.514(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C26 C27 1.388(4) . ?
C26 C31 1.385(4) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.389(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.378(6) . ?
C30 H30 0.9500 . ?
C30 C31 1.380(5) . ?
C31 H31 0.9500 . ?

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
O32 S16 C13 108.37(11) . . ?
O32 S16 C17 107.09(12) . . ?
C13 S16 C17 96.86(12) . . ?
C10 O25 H25 109.5 . . ?
N15 N11 C23 122.2(2) . . ?
C12 N11 N15 111.0(2) . . ?
C12 N11 C23 126.5(2) . . ?
N15 N14 C13 108.2(2) . . ?
N14 N15 N11 107.6(2) . . ?
C2 C1 C12 121.0(2) . . ?
C10 C1 C2 120.6(2) . . ?
C10 C1 C12 118.4(2) . . ?
C3 C2 C1 122.1(2) . . ?
C7 C2 C1 119.0(2) . . ?
C7 C2 C3 118.9(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.3(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(3) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 119.0(3) . . ?
C2 C7 C8 118.6(2) . . ?
C6 C7 C8 122.4(3) . . ?
C7 C8 H8 119.1 . . ?
C9 C8 C7 121.8(3) . . ?
C9 C8 H8 119.1 . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(3) . . ?
C10 C9 H9 120.0 . . ?
O25 C10 C1 117.8(2) . . ?
O25 C10 C9 122.2(2) . . ?
C1 C10 C9 119.9(2) . . ?
N11 C12 C1 123.8(2) . . ?
N11 C12 C13 103.5(2) . . ?
C13 C12 C1 132.7(2) . . ?
N14 C13 S16 125.89(19) . . ?
N14 C13 C12 109.8(2) . . ?
C12 C13 S16 124.2(2) . . ?
C18 C17 S16 116.7(2) . . ?
C22 C17 S16 120.7(2) . . ?
C22 C17 C18 122.6(3) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.1(3) . . ?
C19 C18 H18 120.4 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.7(4) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.3 . . ?
C19 C20 C21 121.4(3) . . ?
C21 C20 H20 119.3 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.8(4) . . ?
C22 C21 H21 120.1 . . ?
C17 C22 C21 117.3(4) . . ?
C17 C22 H22 121.3 . . ?
C21 C22 H22 121.3 . . ?
N11 C23 H23 107.4 . . ?
N11 C23 C24 110.1(2) . . ?
N11 C23 C26 111.8(2) . . ?
C24 C23 H23 107.4 . . ?
C26 C23 H23 107.4 . . ?
C26 C23 C24 112.4(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C27 C26 C23 121.1(3) . . ?
C31 C26 C23 119.6(3) . . ?
C31 C26 C27 119.3(3) . . ?
C26 C27 H27 120.0 . . ?
C26 C27 C28 120.0(3) . . ?
C28 C27 H27 120.0 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C30 C29 C28 120.0(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.9(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.8(3) . . ?
C30 C31 H31 119.6 . . ?

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
S16 C17 C18 C19 177.1(2) . . . . ?
S16 C17 C22 C21 -177.6(2) . . . . ?
O32 S16 C13 N14 76.7(3) . . . . ?
O32 S16 C13 C12 -108.7(2) . . . . ?
O32 S16 C17 C18 151.6(2) . . . . ?
O32 S16 C17 C22 -28.7(2) . . . . ?
N11 C12 C13 S16 -174.32(19) . . . . ?
N11 C12 C13 N14 1.0(3) . . . . ?
N11 C23 C26 C27 58.1(3) . . . . ?
N11 C23 C26 C31 -123.0(3) . . . . ?
N15 N11 C12 C1 178.3(2) . . . . ?
N15 N11 C12 C13 -0.9(3) . . . . ?
N15 N11 C23 C24 28.4(3) . . . . ?
N15 N11 C23 C26 -97.3(3) . . . . ?
N15 N14 C13 S16 174.4(2) . . . . ?
N15 N14 C13 C12 -0.8(3) . . . . ?
C1 C2 C3 C4 -178.7(3) . . . . ?
C1 C2 C7 C6 179.0(2) . . . . ?
C1 C2 C7 C8 0.7(4) . . . . ?
C1 C12 C13 S16 6.6(4) . . . . ?
C1 C12 C13 N14 -178.1(3) . . . . ?
C2 C1 C10 O25 -179.5(2) . . . . ?
C2 C1 C10 C9 1.4(4) . . . . ?
C2 C1 C12 N11 -79.4(3) . . . . ?
C2 C1 C12 C13 99.5(4) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C7 C8 C9 0.5(4) . . . . ?
C3 C2 C7 C6 0.9(4) . . . . ?
C3 C2 C7 C8 -177.5(2) . . . . ?
C3 C4 C5 C6 0.2(5) . . . . ?
C4 C5 C6 C7 0.1(4) . . . . ?
C5 C6 C7 C2 -0.6(4) . . . . ?
C5 C6 C7 C8 177.6(3) . . . . ?
C6 C7 C8 C9 -177.7(3) . . . . ?
C7 C2 C3 C4 -0.6(4) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C8 C9 C10 O25 -179.2(3) . . . . ?
C8 C9 C10 C1 -0.1(4) . . . . ?
C10 C1 C2 C3 176.4(2) . . . . ?
C10 C1 C2 C7 -1.6(4) . . . . ?
C10 C1 C12 N11 101.9(3) . . . . ?
C10 C1 C12 C13 -79.2(4) . . . . ?
C12 N11 N15 N14 0.5(3) . . . . ?
C12 N11 C23 C24 -144.3(3) . . . . ?
C12 N11 C23 C26 90.0(3) . . . . ?
C12 C1 C2 C3 -2.2(4) . . . . ?
C12 C1 C2 C7 179.7(2) . . . . ?
C12 C1 C10 O25 -0.8(4) . . . . ?
C12 C1 C10 C9 -179.9(2) . . . . ?
C13 S16 C17 C18 -96.7(2) . . . . ?
C13 S16 C17 C22 83.0(2) . . . . ?
C13 N14 N15 N11 0.2(3) . . . . ?
C17 S16 C13 N14 -33.9(3) . . . . ?
C17 S16 C13 C12 140.7(2) . . . . ?
C17 C18 C19 C20 0.9(5) . . . . ?
C18 C17 C22 C21 2.0(4) . . . . ?
C18 C19 C20 C21 1.2(5) . . . . ?
C19 C20 C21 C22 -1.7(5) . . . . ?
C20 C21 C22 C17 0.1(4) . . . . ?
C22 C17 C18 C19 -2.6(4) . . . . ?
C23 N11 N15 N14 -173.3(2) . . . . ?
C23 N11 C12 C1 -8.3(4) . . . . ?
C23 N11 C12 C13 172.5(2) . . . . ?
C23 C26 C27 C28 178.8(3) . . . . ?
C23 C26 C31 C30 -179.1(3) . . . . ?
C24 C23 C26 C27 -66.2(3) . . . . ?
C24 C23 C26 C31 112.6(3) . . . . ?
C26 C27 C28 C29 1.0(5) . . . . ?
C27 C26 C31 C30 -0.2(5) . . . . ?
C27 C28 C29 C30 -1.8(6) . . . . ?
C28 C29 C30 C31 1.6(6) . . . . ?
C29 C30 C31 C26 -0.6(5) . . . . ?
C31 C26 C27 C28 0.0(5) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-25
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.174
_oxdiff_exptl_absorpt_empirical_full_min 0.863
####################################################################### 
# 
# 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_wdh1063
_database_code_depnum_ccdc_archive 'CCDC 2076359'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-03-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N3 O2 S'
_chemical_formula_sum            'C26 H21 N3 O2 S'
_chemical_formula_weight         439.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H21 N3 S1 O2'
_chemical_oxdiff_usercomment     'RV-33 t4 dia 1'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   21.3972(3)
_cell_length_b                   14.6607(2)
_cell_length_c                   6.86195(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2152.58(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7079
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      28.5370
_cell_measurement_theta_min      3.2630
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            15539
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.779
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  25.00   1.00  120.00    --  -17.00 -99.00-150.00   45
  2  ω    -90.00  27.00   1.00  120.00    --  -17.00 -19.00  30.00  117
  3  ω    -90.00  56.00   1.00  120.00    --  -17.00   0.00  90.00  146
  4  ω    -61.00 -36.00   1.00  120.00    --  -17.00  19.00-150.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0058822000
_diffrn_orient_matrix_UB_12      -0.0415732000
_diffrn_orient_matrix_UB_13      0.0496586000
_diffrn_orient_matrix_UB_21      -0.0311400000
_diffrn_orient_matrix_UB_22      -0.0001069000
_diffrn_orient_matrix_UB_23      0.0353424000
_diffrn_orient_matrix_UB_31      -0.0097003000
_diffrn_orient_matrix_UB_32      -0.0247828000
_diffrn_orient_matrix_UB_33      -0.0834797000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                4121
_reflns_number_total             4400
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details 
;
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0318
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.4442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0709
_refine_ls_wR_factor_ref         0.0723
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C -0.01216(9) 0.91210(16) 0.8054(3) 0.0120(5) Uani 1 1 d . . . . .
C2 C -0.07173(10) 0.88427(16) 0.7317(3) 0.0131(5) Uani 1 1 d . . . . .
C3 C -0.09339(9) 0.90834(15) 0.5439(4) 0.0150(5) Uani 1 1 d . . . . .
H3 H -0.0680 0.9448 0.4613 0.018 Uiso 1 1 calc R . . . .
C4 C -0.15059(10) 0.87962(17) 0.4803(4) 0.0187(5) Uani 1 1 d . . . . .
H4 H -0.1647 0.8969 0.3543 0.022 Uiso 1 1 calc R . . . .
C5 C -0.18897(10) 0.82478(17) 0.5989(4) 0.0205(5) Uani 1 1 d . . . . .
H5 H -0.2285 0.8049 0.5526 0.025 Uiso 1 1 calc R . . . .
C6 C -0.16918(10) 0.80043(17) 0.7801(4) 0.0186(5) Uani 1 1 d . . . . .
H6 H -0.1953 0.7636 0.8597 0.022 Uiso 1 1 calc R . . . .
C7 C -0.11026(10) 0.82900(16) 0.8522(3) 0.0145(5) Uani 1 1 d . . . . .
C8 C -0.08827(10) 0.80324(15) 1.0381(4) 0.0160(5) Uani 1 1 d . . . . .
H8 H -0.1142 0.7672 1.1199 0.019 Uiso 1 1 calc R . . . .
C9 C -0.03084(10) 0.82875(17) 1.1032(3) 0.0156(5) Uani 1 1 d . . . . .
H9 H -0.0169 0.8102 1.2285 0.019 Uiso 1 1 calc R . . . .
C10 C 0.00810(10) 0.88290(16) 0.9840(3) 0.0143(5) Uani 1 1 d . . . . .
N11 N 0.02772(8) 1.06081(13) 0.6636(3) 0.0147(4) Uani 1 1 d . . . . .
C12 C 0.03007(10) 0.96889(15) 0.6853(3) 0.0126(5) Uani 1 1 d . . . . .
C13 C 0.08020(9) 0.94397(15) 0.5733(3) 0.0132(5) Uani 1 1 d . . . . .
N14 N 0.10593(8) 1.01869(13) 0.4871(3) 0.0181(4) Uani 1 1 d . . . . .
N15 N 0.07387(8) 1.08980(13) 0.5424(3) 0.0195(4) Uani 1 1 d . . . . .
S16 S 0.10922(2) 0.83201(4) 0.54731(8) 0.01264(13) Uani 1 1 d . . . . .
C17 C 0.19037(9) 0.85955(15) 0.5613(4) 0.0154(5) Uani 1 1 d . . . . .
C18 C 0.21863(11) 0.85221(17) 0.7425(4) 0.0205(5) Uani 1 1 d . . . . .
H18 H 0.1961 0.8298 0.8518 0.025 Uiso 1 1 calc R . . . .
C19 C 0.28066(11) 0.87850(19) 0.7599(4) 0.0278(7) Uani 1 1 d . . . . .
H19 H 0.3009 0.8751 0.8828 0.033 Uiso 1 1 calc R . . . .
C20 C 0.31282(11) 0.90941(18) 0.5997(4) 0.0282(7) Uani 1 1 d . . . . .
H20 H 0.3552 0.9278 0.6135 0.034 Uiso 1 1 calc R . . . .
C21 C 0.28449(11) 0.91413(18) 0.4184(5) 0.0270(6) Uani 1 1 d . . . . .
H21 H 0.3075 0.9347 0.3084 0.032 Uiso 1 1 calc R . . . .
C22 C 0.22199(11) 0.88854(17) 0.3984(4) 0.0203(6) Uani 1 1 d . . . . .
H22 H 0.2018 0.8911 0.2752 0.024 Uiso 1 1 calc R . . . .
C23 C -0.01056(10) 1.13151(17) 0.7628(4) 0.0185(5) Uani 1 1 d . . . . .
H23 H 0.0030 1.1917 0.7086 0.022 Uiso 1 1 calc R . . . .
C24 C 0.00563(12) 1.13280(19) 0.9791(4) 0.0277(6) Uani 1 1 d . . . . .
H24A H -0.0019 1.0723 1.0352 0.042 Uiso 1 1 calc GR . . . .
H24B H -0.0205 1.1779 1.0458 0.042 Uiso 1 1 calc GR . . . .
H24C H 0.0498 1.1490 0.9955 0.042 Uiso 1 1 calc GR . . . .
O25 O 0.06603(7) 0.90878(11) 1.0437(3) 0.0187(4) Uani 1 1 d . . . . .
H25 H 0.0750 0.8816 1.1478 0.028 Uiso 1 1 calc GR . . . .
C26 C -0.07925(10) 1.12094(16) 0.7119(4) 0.0170(5) Uani 1 1 d . . . . .
C27 C -0.09910(10) 1.14848(16) 0.5292(4) 0.0193(5) Uani 1 1 d . . . . .
H27 H -0.0697 1.1728 0.4392 0.023 Uiso 1 1 calc R . . . .
C28 C -0.16169(11) 1.14092(17) 0.4758(4) 0.0247(6) Uani 1 1 d . . . . .
H28 H -0.1749 1.1596 0.3498 0.030 Uiso 1 1 calc R . . . .
C29 C -0.20448(11) 1.10627(18) 0.6065(4) 0.0266(7) Uani 1 1 d . . . . .
H29 H -0.2472 1.1010 0.5704 0.032 Uiso 1 1 calc R . . . .
C30 C -0.18526(11) 1.07928(18) 0.7897(4) 0.0245(6) Uani 1 1 d . . . . .
H30 H -0.2148 1.0553 0.8795 0.029 Uiso 1 1 calc R . . . .
C31 C -0.12273(11) 1.08705(17) 0.8434(4) 0.0205(5) Uani 1 1 d . . . . .
H31 H -0.1098 1.0691 0.9702 0.025 Uiso 1 1 calc R . . . .
O32 O 0.09688(7) 0.80264(11) 0.3404(2) 0.0183(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.431(3) . ?
C1 C10 1.368(3) . ?
C1 C12 1.480(3) . ?
C2 C3 1.414(3) . ?
C2 C7 1.421(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.408(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.361(3) . ?
C6 H6 0.9500 . ?
C6 C7 1.418(3) . ?
C7 C8 1.411(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.360(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.412(3) . ?
C10 O25 1.360(2) . ?
N11 C12 1.357(3) . ?
N11 N15 1.359(3) . ?
N11 C23 1.486(3) . ?
C12 C13 1.369(3) . ?
C13 N14 1.361(3) . ?
C13 S16 1.764(2) . ?
N14 N15 1.304(3) . ?
S16 C17 1.785(2) . ?
S16 O32 1.5073(17) . ?
C17 C18 1.387(3) . ?
C17 C22 1.374(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.387(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.374(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.396(3) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.525(4) . ?
C23 C26 1.519(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
C26 C27 1.384(3) . ?
C26 C31 1.388(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.393(3) . ?
C28 H28 0.9500 . ?
C28 C29 1.378(4) . ?
C29 H29 0.9500 . ?
C29 C30 1.381(4) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(3) . ?
C31 H31 0.9500 . ?

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 C12 120.5(2) . . ?
C10 C1 C2 120.6(2) . . ?
C10 C1 C12 118.78(19) . . ?
C3 C2 C1 122.9(2) . . ?
C3 C2 C7 118.8(2) . . ?
C7 C2 C1 118.3(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 120.9(2) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.7(2) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 H6 119.4 . . ?
C5 C6 C7 121.2(2) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 C2 118.8(2) . . ?
C8 C7 C2 119.0(2) . . ?
C8 C7 C6 122.2(2) . . ?
C7 C8 H8 119.2 . . ?
C9 C8 C7 121.6(2) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 H9 120.1 . . ?
C8 C9 C10 119.8(2) . . ?
C10 C9 H9 120.1 . . ?
C1 C10 C9 120.5(2) . . ?
O25 C10 C1 118.1(2) . . ?
O25 C10 C9 121.4(2) . . ?
C12 N11 N15 110.55(19) . . ?
C12 N11 C23 131.5(2) . . ?
N15 N11 C23 117.55(19) . . ?
N11 C12 C1 126.7(2) . . ?
N11 C12 C13 103.4(2) . . ?
C13 C12 C1 129.9(2) . . ?
C12 C13 S16 125.52(18) . . ?
N14 C13 C12 110.2(2) . . ?
N14 C13 S16 124.22(16) . . ?
N15 N14 C13 107.70(18) . . ?
N14 N15 N11 108.07(18) . . ?
C13 S16 C17 97.27(10) . . ?
O32 S16 C13 107.43(10) . . ?
O32 S16 C17 106.59(11) . . ?
C18 C17 S16 117.04(18) . . ?
C22 C17 S16 120.35(19) . . ?
C22 C17 C18 122.6(2) . . ?
C17 C18 H18 120.9 . . ?
C17 C18 C19 118.2(2) . . ?
C19 C18 H18 120.9 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.1(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(2) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 120.2 . . ?
C20 C21 C22 119.6(3) . . ?
C22 C21 H21 120.2 . . ?
C17 C22 C21 118.4(2) . . ?
C17 C22 H22 120.8 . . ?
C21 C22 H22 120.8 . . ?
N11 C23 H23 106.6 . . ?
N11 C23 C24 109.24(19) . . ?
N11 C23 C26 110.9(2) . . ?
C24 C23 H23 106.6 . . ?
C26 C23 H23 106.6 . . ?
C26 C23 C24 116.4(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C10 O25 H25 109.5 . . ?
C27 C26 C23 118.4(2) . . ?
C27 C26 C31 119.2(2) . . ?
C31 C26 C23 122.4(2) . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.7(2) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.8(2) . . ?
C29 C28 H28 120.1 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.0(2) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 119.9 . . ?
C29 C30 C31 120.2(2) . . ?
C31 C30 H30 119.9 . . ?
C26 C31 C30 120.1(2) . . ?
C26 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?

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
C1 C2 C3 C4 179.7(2) . . . . ?
C1 C2 C7 C6 -179.5(2) . . . . ?
C1 C2 C7 C8 -0.5(3) . . . . ?
C1 C12 C13 N14 -179.9(2) . . . . ?
C1 C12 C13 S16 -1.4(4) . . . . ?
C2 C1 C10 C9 -3.4(3) . . . . ?
C2 C1 C10 O25 177.6(2) . . . . ?
C2 C1 C12 N11 82.3(3) . . . . ?
C2 C1 C12 C13 -98.5(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C7 C8 C9 -1.1(3) . . . . ?
C3 C2 C7 C6 -0.3(3) . . . . ?
C3 C2 C7 C8 178.7(2) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C7 -0.3(4) . . . . ?
C5 C6 C7 C2 0.2(3) . . . . ?
C5 C6 C7 C8 -178.8(2) . . . . ?
C6 C7 C8 C9 177.9(2) . . . . ?
C7 C2 C3 C4 0.6(3) . . . . ?
C7 C8 C9 C10 0.5(4) . . . . ?
C8 C9 C10 C1 1.8(3) . . . . ?
C8 C9 C10 O25 -179.3(2) . . . . ?
C10 C1 C2 C3 -176.4(2) . . . . ?
C10 C1 C2 C7 2.7(3) . . . . ?
C10 C1 C12 N11 -100.9(3) . . . . ?
C10 C1 C12 C13 78.2(3) . . . . ?
N11 C12 C13 N14 -0.7(3) . . . . ?
N11 C12 C13 S16 177.88(17) . . . . ?
N11 C23 C26 C27 -75.1(3) . . . . ?
N11 C23 C26 C31 106.7(3) . . . . ?
C12 C1 C2 C3 0.2(3) . . . . ?
C12 C1 C2 C7 179.4(2) . . . . ?
C12 C1 C10 C9 179.9(2) . . . . ?
C12 C1 C10 O25 0.9(3) . . . . ?
C12 N11 N15 N14 -0.4(3) . . . . ?
C12 N11 C23 C24 62.9(3) . . . . ?
C12 N11 C23 C26 -66.7(3) . . . . ?
C12 C13 N14 N15 0.4(3) . . . . ?
C12 C13 S16 C17 -137.8(2) . . . . ?
C12 C13 S16 O32 112.2(2) . . . . ?
C13 N14 N15 N11 0.0(2) . . . . ?
C13 S16 C17 C18 95.0(2) . . . . ?
C13 S16 C17 C22 -83.6(2) . . . . ?
N14 C13 S16 C17 40.6(2) . . . . ?
N14 C13 S16 O32 -69.4(2) . . . . ?
N15 N11 C12 C1 180.0(2) . . . . ?
N15 N11 C12 C13 0.6(2) . . . . ?
N15 N11 C23 C24 -109.1(2) . . . . ?
N15 N11 C23 C26 121.2(2) . . . . ?
S16 C13 N14 N15 -178.11(17) . . . . ?
S16 C17 C18 C19 -176.14(19) . . . . ?
S16 C17 C22 C21 176.51(18) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C18 C17 C22 C21 -2.0(4) . . . . ?
C18 C19 C20 C21 -0.6(4) . . . . ?
C19 C20 C21 C22 1.1(4) . . . . ?
C20 C21 C22 C17 0.2(4) . . . . ?
C22 C17 C18 C19 2.4(4) . . . . ?
C23 N11 C12 C1 7.5(4) . . . . ?
C23 N11 C12 C13 -171.9(2) . . . . ?
C23 N11 N15 N14 173.28(19) . . . . ?
C23 C26 C27 C28 -179.5(2) . . . . ?
C23 C26 C31 C30 179.6(2) . . . . ?
C24 C23 C26 C27 159.2(2) . . . . ?
C24 C23 C26 C31 -19.0(3) . . . . ?
C26 C27 C28 C29 0.5(4) . . . . ?
C27 C26 C31 C30 1.3(4) . . . . ?
C27 C28 C29 C30 0.1(4) . . . . ?
C28 C29 C30 C31 0.1(4) . . . . ?
C29 C30 C31 C26 -0.8(4) . . . . ?
C31 C26 C27 C28 -1.1(4) . . . . ?
O32 S16 C17 C18 -154.30(18) . . . . ?
O32 S16 C17 C22 27.1(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-02-29
_olex2_submission_original_sample_id 'RV-33-A t4'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.303
_oxdiff_exptl_absorpt_empirical_full_min 0.838
####################################################################### 
# 
# 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_wdh1064
_database_code_depnum_ccdc_archive 'CCDC 2076360'
loop_
_audit_author_name
_audit_author_address
'Luc Van Meervelt'
;KU Leuven
Belgium
;
_audit_update_record             
;
2021-04-09 deposited with the CCDC.	2021-07-05 downloaded from the CCDC.
;
_audit_creation_date             2016-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H21 N3 O2 S'
_chemical_formula_sum            'C26 H21 N3 O2 S'
_chemical_formula_weight         439.52
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H21 N3 S1 O2'
_chemical_oxdiff_usercomment     'RV-33B t10 dia 2'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   8.2288(5)
_cell_length_b                   10.1233(6)
_cell_length_c                   25.6942(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2140.4(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4553
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.2550
_cell_measurement_theta_min      2.9010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.181
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84723
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0648
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19890
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.562
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9631
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  63.00   1.00  150.00    --   19.03 -19.00-180.00  117
  2  ω     -6.00  91.00   1.00  150.00    --   19.03  38.00  30.00   97
  3  ω    -87.00  13.00   1.00  150.00    --  -17.00 -77.00-150.00  100
  4  ω     34.00  96.00   1.00  150.00    --   19.03-178.00-150.00   62
  5  ω     -2.00  25.00   1.00  150.00    --   19.03  57.00 150.00   27
  6  ω     34.00  96.00   1.00  150.00    --   19.03-178.00 120.00   62
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0215187000
_diffrn_orient_matrix_UB_12      0.0392788000
_diffrn_orient_matrix_UB_13      0.0217870000
_diffrn_orient_matrix_UB_21      0.0831130000
_diffrn_orient_matrix_UB_22      0.0049904000
_diffrn_orient_matrix_UB_23      0.0070352000
_diffrn_orient_matrix_UB_31      0.0074783000
_diffrn_orient_matrix_UB_32      0.0578614000
_diffrn_orient_matrix_UB_33      -0.0154026000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.741
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3615
_reflns_number_total             4376
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1245 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0464
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.2326P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0820
_refine_ls_wR_factor_ref         0.0873
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C8(H8), C9(H9), C18(H18), C19(H19), C20(H20),
 C21(H21), C22(H22), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.d Idealised tetrahedral OH refined as rotating group:
 O25(H25)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
C1 C 0.9321(4) 0.2404(3) 0.59571(12) 0.0129(7) Uani 1 1 d . . . . .
C2 C 0.9475(4) 0.2050(3) 0.54410(12) 0.0148(8) Uani 1 1 d . . . . .
C3 C 1.0433(4) 0.0947(3) 0.52982(14) 0.0192(8) Uani 1 1 d . . . . .
H3 H 1.0517 0.0699 0.4943 0.023 Uiso 1 1 calc R . . . .
C4 C 1.1234(4) 0.0243(3) 0.56680(14) 0.0205(8) Uani 1 1 d . . . . .
H4 H 1.1901 -0.0477 0.5565 0.025 Uiso 1 1 calc R . . . .
C5 C 1.1098(4) 0.0558(3) 0.62038(14) 0.0185(8) Uani 1 1 d . . . . .
C6 C 1.1949(5) -0.0153(3) 0.65923(15) 0.0246(9) Uani 1 1 d . . . . .
H6 H 1.2637 -0.0864 0.6493 0.029 Uiso 1 1 calc R . . . .
C7 C 1.1799(5) 0.0165(3) 0.71057(14) 0.0251(9) Uani 1 1 d . . . . .
H7 H 1.2372 -0.0327 0.7361 0.030 Uiso 1 1 calc R . . . .
C8 C 1.0793(4) 0.1224(3) 0.72566(14) 0.0238(9) Uani 1 1 d . . . . .
H8 H 1.0681 0.1436 0.7615 0.029 Uiso 1 1 calc R . . . .
C9 C 0.9971(4) 0.1954(3) 0.68910(12) 0.0175(8) Uani 1 1 d . . . . .
H9 H 0.9302 0.2667 0.7000 0.021 Uiso 1 1 calc R . . . .
C10 C 1.0109(4) 0.1656(3) 0.63527(12) 0.0151(7) Uani 1 1 d . . . . .
N11 N 0.8949(3) 0.4846(3) 0.60839(10) 0.0156(6) Uani 1 1 d . . . . .
C12 C 0.8355(4) 0.3591(3) 0.60863(12) 0.0136(7) Uani 1 1 d . . . . .
C13 C 0.6761(4) 0.3768(3) 0.62317(13) 0.0152(7) Uani 1 1 d . . . . .
N14 N 0.6447(3) 0.5080(3) 0.63124(11) 0.0184(7) Uani 1 1 d . . . . .
N15 N 0.7797(3) 0.5739(3) 0.62193(11) 0.0196(7) Uani 1 1 d . . . . .
S16 S 0.52353(10) 0.25527(8) 0.62643(3) 0.0172(2) Uani 1 1 d . . . . .
C17 C 0.4556(4) 0.2891(3) 0.69129(12) 0.0149(7) Uani 1 1 d . . . . .
C18 C 0.3362(4) 0.3827(3) 0.69951(13) 0.0180(8) Uani 1 1 d . . . . .
H18 H 0.2914 0.4307 0.6712 0.022 Uiso 1 1 calc R . . . .
C19 C 0.2827(4) 0.4052(3) 0.75008(13) 0.0198(8) Uani 1 1 d . . . . .
H19 H 0.2007 0.4692 0.7565 0.024 Uiso 1 1 calc R . . . .
C20 C 0.3483(4) 0.3350(4) 0.79084(13) 0.0232(9) Uani 1 1 d . . . . .
H20 H 0.3111 0.3505 0.8253 0.028 Uiso 1 1 calc R . . . .
C21 C 0.4684(4) 0.2417(4) 0.78189(12) 0.0250(8) Uani 1 1 d . . . . .
H21 H 0.5137 0.1939 0.8102 0.030 Uiso 1 1 calc R . . . .
C22 C 0.5223(4) 0.2179(3) 0.73177(13) 0.0202(8) Uani 1 1 d . . . . .
H22 H 0.6039 0.1536 0.7253 0.024 Uiso 1 1 calc R . . . .
C23 C 1.0563(4) 0.5320(3) 0.59119(13) 0.0152(7) Uani 1 1 d . . . . .
H23 H 1.1329 0.4553 0.5918 0.018 Uiso 1 1 calc R . . . .
C24 C 1.1196(4) 0.6358(3) 0.62906(13) 0.0199(8) Uani 1 1 d . . . . .
H24A H 1.0504 0.7144 0.6274 0.030 Uiso 1 1 calc GR . . . .
H24B H 1.2312 0.6597 0.6196 0.030 Uiso 1 1 calc GR . . . .
H24C H 1.1180 0.5999 0.6645 0.030 Uiso 1 1 calc GR . . . .
O25 O 0.8662(3) 0.2791(2) 0.50875(8) 0.0190(6) Uani 1 1 d . . . . .
H25 H 0.8931 0.2558 0.4786 0.029 Uiso 1 1 calc GR . . . .
C26 C 1.0479(4) 0.5833(3) 0.53551(12) 0.0140(7) Uani 1 1 d . . . . .
C27 C 1.1274(4) 0.5163(3) 0.49609(13) 0.0201(8) Uani 1 1 d . . . . .
H27 H 1.1826 0.4361 0.5036 0.024 Uiso 1 1 calc R . . . .
C28 C 1.1271(5) 0.5654(4) 0.44563(14) 0.0225(9) Uani 1 1 d . . . . .
H28 H 1.1822 0.5189 0.4188 0.027 Uiso 1 1 calc R . . . .
C29 C 1.0466(4) 0.6822(3) 0.43450(13) 0.0216(8) Uani 1 1 d . . . . .
H29 H 1.0469 0.7160 0.4000 0.026 Uiso 1 1 calc R . . . .
C30 C 0.9655(4) 0.7497(3) 0.47360(12) 0.0205(7) Uani 1 1 d . . . . .
H30 H 0.9100 0.8296 0.4660 0.025 Uiso 1 1 calc R . . . .
C31 C 0.9658(4) 0.6999(3) 0.52410(13) 0.0181(8) Uani 1 1 d . . . . .
H31 H 0.9096 0.7458 0.5509 0.022 Uiso 1 1 calc R . . . .
O32 O 0.3910(3) 0.3015(2) 0.59040(8) 0.0231(6) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.380(4) . ?
C1 C10 1.424(4) . ?
C1 C12 1.479(4) . ?
C2 C3 1.415(5) . ?
C2 O25 1.355(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.358(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.418(5) . ?
C5 C6 1.416(5) . ?
C5 C10 1.430(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.364(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.409(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.373(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.420(4) . ?
N11 C12 1.361(4) . ?
N11 N15 1.355(4) . ?
N11 C23 1.480(4) . ?
C12 C13 1.375(5) . ?
C13 N14 1.369(4) . ?
C13 S16 1.760(3) . ?
N14 N15 1.318(4) . ?
S16 C17 1.791(3) . ?
S16 O32 1.505(2) . ?
C17 C18 1.382(4) . ?
C17 C22 1.379(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.376(5) . ?
C20 H20 0.9500 . ?
C20 C21 1.386(5) . ?
C21 H21 0.9500 . ?
C21 C22 1.383(4) . ?
C22 H22 0.9500 . ?
C23 H23 1.0000 . ?
C23 C24 1.524(4) . ?
C23 C26 1.524(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O25 H25 0.8400 . ?
C26 C27 1.383(4) . ?
C26 C31 1.392(5) . ?
C27 H27 0.9500 . ?
C27 C28 1.389(5) . ?
C28 H28 0.9500 . ?
C28 C29 1.385(5) . ?
C29 H29 0.9500 . ?
C29 C30 1.386(5) . ?
C30 H30 0.9500 . ?
C30 C31 1.392(4) . ?
C31 H31 0.9500 . ?

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 C10 120.4(3) . . ?
C2 C1 C12 118.5(3) . . ?
C10 C1 C12 121.1(3) . . ?
C1 C2 C3 120.4(3) . . ?
O25 C2 C1 117.0(3) . . ?
O25 C2 C3 122.6(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.5(3) . . ?
C5 C4 H4 119.2 . . ?
C4 C5 C10 118.7(3) . . ?
C6 C5 C4 122.1(3) . . ?
C6 C5 C10 119.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.2(4) . . ?
C7 C6 H6 119.4 . . ?
C6 C7 H7 120.0 . . ?
C6 C7 C8 119.9(3) . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.7(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.6 . . ?
C8 C9 C10 120.9(3) . . ?
C10 C9 H9 119.6 . . ?
C1 C10 C5 118.8(3) . . ?
C9 C10 C1 123.1(3) . . ?
C9 C10 C5 118.1(3) . . ?
C12 N11 C23 128.8(3) . . ?
N15 N11 C12 111.7(3) . . ?
N15 N11 C23 119.2(3) . . ?
N11 C12 C1 124.4(3) . . ?
N11 C12 C13 102.8(3) . . ?
C13 C12 C1 132.8(3) . . ?
C12 C13 S16 127.0(2) . . ?
N14 C13 C12 110.4(3) . . ?
N14 C13 S16 122.4(3) . . ?
N15 N14 C13 107.7(3) . . ?
N14 N15 N11 107.4(2) . . ?
C13 S16 C17 97.66(15) . . ?
O32 S16 C13 105.69(15) . . ?
O32 S16 C17 106.68(15) . . ?
C18 C17 S16 119.7(3) . . ?
C22 C17 S16 118.6(3) . . ?
C22 C17 C18 121.7(3) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.7(3) . . ?
C19 C18 H18 120.6 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.4(3) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 119.0(3) . . ?
C17 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
N11 C23 H23 108.0 . . ?
N11 C23 C24 109.9(3) . . ?
N11 C23 C26 110.5(3) . . ?
C24 C23 H23 108.0 . . ?
C26 C23 H23 108.0 . . ?
C26 C23 C24 112.3(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C2 O25 H25 109.5 . . ?
C27 C26 C23 119.9(3) . . ?
C27 C26 C31 119.4(3) . . ?
C31 C26 C23 120.6(3) . . ?
C26 C27 H27 119.8 . . ?
C26 C27 C28 120.5(3) . . ?
C28 C27 H27 119.8 . . ?
C27 C28 H28 120.0 . . ?
C29 C28 C27 119.9(3) . . ?
C29 C28 H28 120.0 . . ?
C28 C29 H29 120.0 . . ?
C28 C29 C30 120.1(3) . . ?
C30 C29 H29 120.0 . . ?
C29 C30 H30 120.1 . . ?
C29 C30 C31 119.8(3) . . ?
C31 C30 H30 120.1 . . ?
C26 C31 C30 120.3(3) . . ?
C26 C31 H31 119.9 . . ?
C30 C31 H31 119.9 . . ?

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
C1 C2 C3 C4 -1.2(5) . . . . ?
C1 C12 C13 N14 179.6(3) . . . . ?
C1 C12 C13 S16 -5.4(6) . . . . ?
C2 C1 C10 C5 1.8(5) . . . . ?
C2 C1 C10 C9 -178.7(3) . . . . ?
C2 C1 C12 N11 -84.9(4) . . . . ?
C2 C1 C12 C13 95.2(4) . . . . ?
C2 C3 C4 C5 2.0(5) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C3 C4 C5 C10 -0.9(5) . . . . ?
C4 C5 C6 C7 -179.9(3) . . . . ?
C4 C5 C10 C1 -1.0(4) . . . . ?
C4 C5 C10 C9 179.4(3) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C6 C5 C10 C1 177.0(3) . . . . ?
C6 C5 C10 C9 -2.5(5) . . . . ?
C6 C7 C8 C9 -0.7(5) . . . . ?
C7 C8 C9 C10 0.3(5) . . . . ?
C8 C9 C10 C1 -178.2(3) . . . . ?
C8 C9 C10 C5 1.4(5) . . . . ?
C10 C1 C2 C3 -0.7(5) . . . . ?
C10 C1 C2 O25 178.6(3) . . . . ?
C10 C1 C12 N11 93.6(4) . . . . ?
C10 C1 C12 C13 -86.2(5) . . . . ?
C10 C5 C6 C7 2.2(5) . . . . ?
N11 C12 C13 N14 -0.2(4) . . . . ?
N11 C12 C13 S16 174.7(3) . . . . ?
N11 C23 C26 C27 -112.4(3) . . . . ?
N11 C23 C26 C31 70.0(4) . . . . ?
C12 C1 C2 C3 177.9(3) . . . . ?
C12 C1 C2 O25 -2.8(4) . . . . ?
C12 C1 C10 C5 -176.7(3) . . . . ?
C12 C1 C10 C9 2.8(5) . . . . ?
C12 N11 N15 N14 0.2(4) . . . . ?
C12 N11 C23 C24 -138.6(3) . . . . ?
C12 N11 C23 C26 96.8(4) . . . . ?
C12 C13 N14 N15 0.3(4) . . . . ?
C12 C13 S16 C17 128.7(3) . . . . ?
C12 C13 S16 O32 -121.5(3) . . . . ?
C13 N14 N15 N11 -0.3(4) . . . . ?
C13 S16 C17 C18 88.0(3) . . . . ?
C13 S16 C17 C22 -93.5(3) . . . . ?
N14 C13 S16 C17 -56.9(3) . . . . ?
N14 C13 S16 O32 52.9(3) . . . . ?
N15 N11 C12 C1 -179.8(3) . . . . ?
N15 N11 C12 C13 0.0(3) . . . . ?
N15 N11 C23 C24 47.9(4) . . . . ?
N15 N11 C23 C26 -76.6(4) . . . . ?
S16 C13 N14 N15 -174.9(2) . . . . ?
S16 C17 C18 C19 178.6(3) . . . . ?
S16 C17 C22 C21 -178.8(3) . . . . ?
C17 C18 C19 C20 0.0(5) . . . . ?
C18 C17 C22 C21 -0.3(5) . . . . ?
C18 C19 C20 C21 0.2(5) . . . . ?
C19 C20 C21 C22 -0.4(5) . . . . ?
C20 C21 C22 C17 0.5(5) . . . . ?
C22 C17 C18 C19 0.1(5) . . . . ?
C23 N11 C12 C1 6.3(5) . . . . ?
C23 N11 C12 C13 -173.8(3) . . . . ?
C23 N11 N15 N14 174.7(3) . . . . ?
C23 C26 C27 C28 -176.9(3) . . . . ?
C23 C26 C31 C30 176.7(3) . . . . ?
C24 C23 C26 C27 124.5(3) . . . . ?
C24 C23 C26 C31 -53.1(4) . . . . ?
O25 C2 C3 C4 179.5(3) . . . . ?
C26 C27 C28 C29 -0.1(5) . . . . ?
C27 C26 C31 C30 -0.9(5) . . . . ?
C27 C28 C29 C30 -0.3(5) . . . . ?
C28 C29 C30 C31 0.2(5) . . . . ?
C29 C30 C31 C26 0.4(5) . . . . ?
C31 C26 C27 C28 0.7(5) . . . . ?
O32 S16 C17 C18 -21.0(3) . . . . ?
O32 S16 C17 C22 157.5(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2016-03-01
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.181
_oxdiff_exptl_absorpt_empirical_full_min 0.766
