# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1561681'
_audit_update_record             
;
2017-07-12 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H24 O2 S2'
_chemical_formula_sum            'C24 H24 O2 S2'
_chemical_formula_weight         408.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 2'
_space_group_name_Hall           'C 2y'

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

_cell_length_a                   23.8323(16)
_cell_length_b                   5.5909(4)
_cell_length_c                   15.6580(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.617(7)
_cell_angle_gamma                90
_cell_volume                     2027.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5867
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      29.91

_exptl_crystal_description       needle
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.280
_shelx_estimated_absorpt_T_min   0.896
_shelx_estimated_absorpt_T_max   0.997
_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_correction_T_min  0.726
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Varimax 50 kV 24 mA Rotating anode'
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            16795
_diffrn_reflns_av_unetI/netI     0.0705
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4907
_reflns_number_gt                3749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.817
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.4 (Rigaku, 2016)'
_computing_publication_material  'CrystalStructure 4.2.4'
_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)+(0.0653P)²+3.0831P] 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_abs_structure_details 
;
 Flack x determined using 1203 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(7)
_chemical_absolute_configuration .
_refine_ls_number_reflns         4907
_refine_ls_number_parameters     293
_refine_ls_number_restraints     281
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1475
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      0.997
_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 0.60791(5) 0.4735(3) 0.36837(8) 0.0334(3) Uani 1 1 d . . . . .
O4 O 0.53837(16) 0.3431(8) 0.1909(2) 0.0451(10) Uani 1 1 d . . . . .
O5 O 0.45442(17) 0.4995(10) 0.1158(3) 0.0577(12) Uani 1 1 d . . . . .
C1 C 0.5029(2) 0.6601(11) 0.2545(4) 0.0412(14) Uani 1 1 d . . . . .
C2 C 0.5493(2) 0.6532(10) 0.3288(4) 0.0339(12) Uani 1 1 d . . . . .
C3 C 0.5454(2) 0.8367(11) 0.3858(3) 0.0354(12) Uani 1 1 d . . . . .
C4 C 0.4951(2) 0.9708(12) 0.3494(3) 0.0403(13) Uani 1 1 d . . . . .
C5 C 0.4783(3) 1.1781(11) 0.3835(4) 0.0458(15) Uani 1 1 d . . . . .
H5 H 0.504724 1.239038 0.433918 0.055 Uiso 1 1 calc R U . . .
C6 C 0.4279(3) 1.3120(14) 0.3545(5) 0.059(2) Uani 1 1 d . . . . .
H6 H 0.424747 1.451830 0.387503 0.071 Uiso 1 1 calc R U . . .
C7 C 0.3834(3) 1.2683(14) 0.2859(5) 0.0596(18) Uani 1 1 d . . . . .
H7 H 0.351970 1.376146 0.280569 0.072 Uiso 1 1 calc R U . . .
C8 C 0.3753(3) 1.0932(14) 0.2216(5) 0.062(2) Uani 1 1 d . . . . .
C9 C 0.4143(2) 0.9111(12) 0.2120(4) 0.0522(18) Uani 1 1 d . . . . .
H9 H 0.402573 0.814391 0.161056 0.063 Uiso 1 1 calc R U . . .
C10 C 0.4677(2) 0.8527(12) 0.2668(4) 0.0436(14) Uani 1 1 d . . . . .
C11 C 0.4939(2) 0.4996(14) 0.1798(4) 0.0478(15) Uani 1 1 d . . . . .
C12 C 0.5365(3) 0.1810(12) 0.1193(4) 0.0486(16) Uani 1 1 d . . . . .
H12A H 0.535934 0.271233 0.064696 0.058 Uiso 1 1 calc R U . . .
H12B H 0.501181 0.081389 0.109602 0.058 Uiso 1 1 calc R U . . .
C13 C 0.5888(3) 0.0271(11) 0.1425(4) 0.0467(16) Uani 1 1 d . . . . .
H13A H 0.590323 -0.053075 0.199353 0.056 Uiso 1 1 calc R U . . .
H13B H 0.623730 0.127841 0.149241 0.056 Uiso 1 1 calc R U . . .
C14 C 0.5883(3) -0.1583(14) 0.0729(4) 0.0610(18) Uani 1 1 d . . . . .
H14A H 0.587212 -0.078015 0.016158 0.073 Uiso 1 1 calc R U . . .
H14B H 0.553173 -0.257816 0.065672 0.073 Uiso 1 1 calc R U . . .
C15 C 0.6411(4) -0.3168(14) 0.0966(6) 0.076(2) Uani 1 1 d . . . . .
H15A H 0.675943 -0.218504 0.104033 0.091 Uiso 1 1 calc R U . . .
H15B H 0.640044 -0.433422 0.049492 0.091 Uiso 1 1 calc R U . . .
H15C H 0.641457 -0.401298 0.151537 0.091 Uiso 1 1 calc R U . . .
C16 C 0.5903(2) 0.8321(11) 0.4632(3) 0.0344(12) Uani 1 1 d . . . . .
H16 H 0.594427 0.946301 0.509221 0.041 Uiso 1 1 calc R U . . .
C17 C 0.6268(2) 0.6461(9) 0.4641(3) 0.0303(11) Uani 1 1 d . . . . .
C18 C 0.6760(2) 0.5812(9) 0.5324(3) 0.0305(11) Uani 0.812(6) 1 d D U P A 1
S2 S 0.70075(14) 0.7596(4) 0.62100(18) 0.0393(7) Uani 0.812(6) 1 d D U P A 1
C19 C 0.7557(5) 0.563(2) 0.6648(8) 0.037(2) Uani 0.812(6) 1 d D U P A 1
H19 H 0.783070 0.588831 0.718833 0.044 Uiso 0.812(6) 1 calc R U P A 1
C20 C 0.7553(6) 0.371(2) 0.6139(6) 0.035(2) Uani 0.812(6) 1 d D U P A 1
H20 H 0.782221 0.243125 0.627024 0.042 Uiso 0.812(6) 1 calc R U P A 1
C21 C 0.7094(9) 0.384(3) 0.5378(15) 0.036(3) Uani 0.812(6) 1 d D U P A 1
H21 H 0.702634 0.262583 0.494007 0.043 Uiso 0.812(6) 1 calc R U P A 1
C118 C 0.6760(2) 0.5812(9) 0.5324(3) 0.0305(11) Uani 0.188(6) 1 d D U P A 2
S12 S 0.7111(9) 0.335(4) 0.5335(16) 0.031(4) Uani 0.188(6) 1 d D U P A 2
C119 C 0.757(3) 0.406(10) 0.633(3) 0.038(10) Uani 0.188(6) 1 d D U P A 2
H119 H 0.786654 0.304765 0.664792 0.045 Uiso 0.188(6) 1 calc R U P A 2
C120 C 0.745(2) 0.624(8) 0.660(3) 0.036(8) Uani 0.188(6) 1 d D U P A 2
H120 H 0.767250 0.702707 0.710662 0.043 Uiso 0.188(6) 1 calc R U P A 2
C121 C 0.695(3) 0.721(9) 0.603(3) 0.048(10) Uani 0.188(6) 1 d D U P A 2
H121 H 0.677008 0.865712 0.613852 0.057 Uiso 0.188(6) 1 calc R U P A 2
C22 C 0.3179(3) 1.0893(17) 0.1500(6) 0.088(3) Uani 1 1 d . . . . .
H22 H 0.296229 1.201150 0.180373 0.105 Uiso 1 1 calc R U . . .
C23 C 0.3183(5) 1.236(3) 0.0789(6) 0.141(6) Uani 1 1 d . . . . .
H23A H 0.278570 1.263911 0.045611 0.169 Uiso 1 1 calc R U . . .
H23B H 0.340260 1.159114 0.040921 0.169 Uiso 1 1 calc R U . . .
H23C H 0.336356 1.389284 0.100005 0.169 Uiso 1 1 calc R U . . .
C24 C 0.2824(4) 0.897(2) 0.1485(7) 0.141(6) Uani 1 1 d . . . . .
H24A H 0.298690 0.757251 0.125006 0.169 Uiso 1 1 calc R U . . .
H24B H 0.244166 0.932347 0.111107 0.169 Uiso 1 1 calc R U . . .
H24C H 0.278747 0.861782 0.208318 0.169 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.714(5) . ?
S1 C17 1.750(5) . ?
O4 C11 1.354(7) . ?
O4 C12 1.434(7) . ?
O5 C11 1.201(6) . ?
C1 C2 1.404(7) . ?
C1 C10 1.405(9) . ?
C1 C11 1.450(9) . ?
C2 C3 1.378(8) . ?
C3 C4 1.414(7) . ?
C3 C16 1.417(7) . ?
C4 C5 1.374(9) . ?
C4 C10 1.462(9) . ?
C5 C6 1.397(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.342(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.410(10) . ?
C8 C22 1.553(10) . ?
C9 C10 1.395(7) . ?
C9 H9 0.9500 . ?
C12 C13 1.488(9) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.502(8) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.511(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.353(7) . ?
C16 H16 0.9500 . ?
C17 C118 1.436(6) . ?
C17 C18 1.436(6) . ?
C18 C21 1.352(16) . ?
C18 S2 1.698(5) . ?
S2 C19 1.722(9) . ?
C19 C20 1.337(11) . ?
C19 H19 0.9500 . ?
C20 C21 1.42(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C118 C121 1.34(3) . ?
C118 S12 1.607(15) . ?
S12 C119 1.73(3) . ?
C119 C120 1.34(2) . ?
C119 H119 0.9500 . ?
C120 C121 1.42(3) . ?
C120 H120 0.9500 . ?
C121 H121 0.9500 . ?
C22 C24 1.368(11) . ?
C22 C23 1.384(11) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C17 90.6(3) . . ?
C11 O4 C12 115.4(4) . . ?
C2 C1 C10 106.7(5) . . ?
C2 C1 C11 126.1(5) . . ?
C10 C1 C11 127.2(5) . . ?
C3 C2 C1 110.8(5) . . ?
C3 C2 S1 112.1(4) . . ?
C1 C2 S1 137.0(5) . . ?
C2 C3 C4 108.3(5) . . ?
C2 C3 C16 112.8(5) . . ?
C4 C3 C16 138.8(6) . . ?
C5 C4 C3 126.0(6) . . ?
C5 C4 C10 127.8(5) . . ?
C3 C4 C10 106.1(5) . . ?
C4 C5 C6 129.3(7) . . ?
C4 C5 H5 115.4 . . ?
C6 C5 H5 115.4 . . ?
C7 C6 C5 128.3(8) . . ?
C7 C6 H6 115.9 . . ?
C5 C6 H6 115.9 . . ?
C6 C7 C8 131.2(7) . . ?
C6 C7 H7 114.4 . . ?
C8 C7 H7 114.4 . . ?
C7 C8 C9 127.3(6) . . ?
C7 C8 C22 118.9(7) . . ?
C9 C8 C22 113.8(8) . . ?
C10 C9 C8 129.2(7) . . ?
C10 C9 H9 115.4 . . ?
C8 C9 H9 115.4 . . ?
C9 C10 C1 125.6(6) . . ?
C9 C10 C4 126.2(6) . . ?
C1 C10 C4 108.1(5) . . ?
O5 C11 O4 122.9(7) . . ?
O5 C11 C1 127.6(6) . . ?
O4 C11 C1 109.5(4) . . ?
O4 C12 C13 107.7(4) . . ?
O4 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O4 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C12 C13 C14 111.1(5) . . ?
C12 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
C12 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 C15 111.3(6) . . ?
C13 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C3 112.1(5) . . ?
C17 C16 H16 123.9 . . ?
C3 C16 H16 123.9 . . ?
C16 C17 C118 127.7(5) . . ?
C16 C17 C18 127.7(5) . . ?
C16 C17 S1 112.4(4) . . ?
C118 C17 S1 119.9(4) . . ?
C18 C17 S1 119.9(4) . . ?
C21 C18 C17 128.3(10) . . ?
C21 C18 S2 110.0(9) . . ?
C17 C18 S2 121.7(4) . . ?
C18 S2 C19 92.1(4) . . ?
C20 C19 S2 112.2(8) . . ?
C20 C19 H19 123.9 . . ?
S2 C19 H19 123.9 . . ?
C19 C20 C21 110.9(11) . . ?
C19 C20 H20 124.6 . . ?
C21 C20 H20 124.6 . . ?
C18 C21 C20 114.8(14) . . ?
C18 C21 H21 122.6 . . ?
C20 C21 H21 122.6 . . ?
C121 C118 C17 121.6(18) . . ?
C121 C118 S12 114.5(16) . . ?
C17 C118 S12 123.8(8) . . ?
C118 S12 C119 91.7(15) . . ?
C120 C119 S12 111(3) . . ?
C120 C119 H119 124.5 . . ?
S12 C119 H119 124.5 . . ?
C119 C120 C121 111(3) . . ?
C119 C120 H120 124.5 . . ?
C121 C120 H120 124.5 . . ?
C118 C121 C120 112(3) . . ?
C118 C121 H121 124.2 . . ?
C120 C121 H121 124.2 . . ?
C24 C22 C23 125.1(9) . . ?
C24 C22 C8 117.4(7) . . ?
C23 C22 C8 113.6(7) . . ?
C24 C22 H22 96.5 . . ?
C23 C22 H22 96.5 . . ?
C8 C22 H22 96.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
C10 C1 C2 C3 -1.5(6) . . . . ?
C11 C1 C2 C3 177.9(5) . . . . ?
C10 C1 C2 S1 176.2(5) . . . . ?
C11 C1 C2 S1 -4.4(9) . . . . ?
C17 S1 C2 C3 0.8(4) . . . . ?
C17 S1 C2 C1 -176.8(6) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
S1 C2 C3 C4 -178.2(4) . . . . ?
C1 C2 C3 C16 178.0(5) . . . . ?
S1 C2 C3 C16 -0.3(6) . . . . ?
C2 C3 C4 C5 -175.1(5) . . . . ?
C16 C3 C4 C5 7.7(10) . . . . ?
C2 C3 C4 C10 1.4(6) . . . . ?
C16 C3 C4 C10 -175.8(6) . . . . ?
C3 C4 C5 C6 -175.7(6) . . . . ?
C10 C4 C5 C6 8.6(10) . . . . ?
C4 C5 C6 C7 0.4(11) . . . . ?
C5 C6 C7 C8 -4.7(12) . . . . ?
C6 C7 C8 C9 -0.7(12) . . . . ?
C6 C7 C8 C22 179.8(7) . . . . ?
C7 C8 C9 C10 4.8(11) . . . . ?
C22 C8 C9 C10 -175.6(6) . . . . ?
C8 C9 C10 C1 176.8(6) . . . . ?
C8 C9 C10 C4 0.9(10) . . . . ?
C2 C1 C10 C9 -174.3(5) . . . . ?
C11 C1 C10 C9 6.4(9) . . . . ?
C2 C1 C10 C4 2.3(6) . . . . ?
C11 C1 C10 C4 -177.1(5) . . . . ?
C5 C4 C10 C9 -9.4(9) . . . . ?
C3 C4 C10 C9 174.2(5) . . . . ?
C5 C4 C10 C1 174.1(5) . . . . ?
C3 C4 C10 C1 -2.3(6) . . . . ?
C12 O4 C11 O5 2.3(9) . . . . ?
C12 O4 C11 C1 -177.0(5) . . . . ?
C2 C1 C11 O5 179.2(6) . . . . ?
C10 C1 C11 O5 -1.6(11) . . . . ?
C2 C1 C11 O4 -1.6(8) . . . . ?
C10 C1 C11 O4 177.6(5) . . . . ?
C11 O4 C12 C13 179.1(5) . . . . ?
O4 C12 C13 C14 176.6(5) . . . . ?
C12 C13 C14 C15 -179.4(6) . . . . ?
C2 C3 C16 C17 -0.7(7) . . . . ?
C4 C3 C16 C17 176.4(6) . . . . ?
C3 C16 C17 C118 -178.2(5) . . . . ?
C3 C16 C17 C18 -178.2(5) . . . . ?
C3 C16 C17 S1 1.3(6) . . . . ?
C2 S1 C17 C16 -1.2(4) . . . . ?
C2 S1 C17 C118 178.3(4) . . . . ?
C2 S1 C17 C18 178.3(4) . . . . ?
C16 C17 C18 C21 173.0(15) . . . . ?
S1 C17 C18 C21 -6.4(16) . . . . ?
C16 C17 C18 S2 -7.7(8) . . . . ?
S1 C17 C18 S2 172.9(3) . . . . ?
C21 C18 S2 C19 -0.4(14) . . . . ?
C17 C18 S2 C19 -179.8(6) . . . . ?
C18 S2 C19 C20 0.2(11) . . . . ?
S2 C19 C20 C21 0.0(19) . . . . ?
C17 C18 C21 C20 179.9(12) . . . . ?
S2 C18 C21 C20 0(2) . . . . ?
C19 C20 C21 C18 0(3) . . . . ?
C16 C17 C118 C121 -7(4) . . . . ?
S1 C17 C118 C121 174(4) . . . . ?
C16 C17 C118 S12 170.5(14) . . . . ?
S1 C17 C118 S12 -8.9(15) . . . . ?
C121 C118 S12 C119 -1(5) . . . . ?
C17 C118 S12 C119 -178(3) . . . . ?
C118 S12 C119 C120 -3(6) . . . . ?
S12 C119 C120 C121 6(9) . . . . ?
C17 C118 C121 C120 -178(4) . . . . ?
S12 C118 C121 C120 4(7) . . . . ?
C119 C120 C121 C118 -7(9) . . . . ?
C7 C8 C22 C24 -114.8(11) . . . . ?
C9 C8 C22 C24 65.6(12) . . . . ?
C7 C8 C22 C23 86.1(11) . . . . ?
C9 C8 C22 C23 -93.5(10) . . . . ?

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.062



####################################################################### 
# 
# 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_shelxl_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1868701'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime University
Japan
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H25 N O2 S'
_chemical_formula_sum            'C25 H25 N O2 S'
_chemical_formula_weight         403.52

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

_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'

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

_cell_length_a                   6.07714(18)
_cell_length_b                   13.1618(3)
_cell_length_c                   27.1117(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2168.56(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    20425
_cell_measurement_theta_min      2.12
_cell_measurement_theta_max      31.21

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.170
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.789
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            37355
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         1.720
_diffrn_reflns_theta_max         27.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5220
_reflns_number_gt                4763
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.737
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0366P)²+0.8909P] 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_abs_structure_details 
;
 Flack x determined using 1837 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5220
_refine_ls_number_parameters     267
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0867
_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_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 0.58298(10) 0.32669(4) 0.36264(2) 0.01598(13) Uani 1 1 d . . . . .
O1 O 0.4834(3) 0.29051(14) 0.19027(6) 0.0229(4) Uani 1 1 d . . . . .
O2 O 0.3613(3) 0.34443(13) 0.26432(6) 0.0185(4) Uani 1 1 d . . . . .
N1 N 0.8526(4) 0.49037(17) 0.59123(8) 0.0225(5) Uani 1 1 d . . . . .
C1 C 0.6749(4) 0.24622(17) 0.26424(9) 0.0165(5) Uani 1 1 d . . . . .
C2 C 0.7088(4) 0.26131(17) 0.31544(9) 0.0157(5) Uani 1 1 d . . . . .
C3 C 0.9033(4) 0.21498(18) 0.33123(9) 0.0166(5) Uani 1 1 d . . . . .
C4 C 0.9979(4) 0.16404(18) 0.29019(9) 0.0170(5) Uani 1 1 d . . . . .
C5 C 1.1906(4) 0.10846(18) 0.29136(10) 0.0204(5) Uani 1 1 d . . . . .
H5 H 1.259020 0.102199 0.322713 0.025 Uiso 1 1 calc R U . . .
C6 C 1.2970(4) 0.06049(19) 0.25233(10) 0.0223(6) Uani 1 1 d . . . . .
H6 H 1.426908 0.024297 0.260775 0.027 Uiso 1 1 calc R U . . .
C7 C 1.2399(4) 0.05819(19) 0.20295(11) 0.0242(6) Uani 1 1 d . . . . .
H7 H 1.340989 0.022584 0.182569 0.029 Uiso 1 1 calc R U . . .
C8 C 1.0594(5) 0.09907(18) 0.17770(10) 0.0218(5) Uani 1 1 d . . . . .
C9 C 0.8865(4) 0.15504(18) 0.19864(9) 0.0195(5) Uani 1 1 d . . . . .
H9 H 0.774819 0.175249 0.176177 0.023 Uiso 1 1 calc R U . . .
C10 C 0.8534(4) 0.18548(17) 0.24716(9) 0.0169(5) Uani 1 1 d . . . . .
C11 C 0.5022(4) 0.29305(17) 0.23482(9) 0.0161(5) Uani 1 1 d . . . . .
C12 C 0.1778(4) 0.39298(19) 0.23993(10) 0.0208(5) Uani 1 1 d . . . . .
H12A H 0.118751 0.347471 0.214571 0.025 Uiso 1 1 calc R U . . .
H12B H 0.227571 0.456287 0.224504 0.025 Uiso 1 1 calc R U . . .
H12C H 0.062794 0.408123 0.264169 0.025 Uiso 1 1 calc R U . . .
C13 C 0.9561(4) 0.23628(17) 0.38131(9) 0.0171(5) Uani 1 1 d . . . . .
H13 H 1.083158 0.210958 0.397599 0.020 Uiso 1 1 calc R U . . .
C14 C 0.8029(4) 0.29733(18) 0.40328(9) 0.0168(5) Uani 1 1 d . . . . .
C15 C 1.0578(5) 0.0831(2) 0.12199(10) 0.0271(6) Uani 1 1 d . . . . .
H15 H 1.162681 0.026482 0.114663 0.032 Uiso 1 1 calc R U . . .
C16 C 0.8349(7) 0.0520(4) 0.10168(14) 0.0643(13) Uani 1 1 d . . . . .
H16A H 0.849460 0.034717 0.066670 0.077 Uiso 1 1 calc R U . . .
H16B H 0.731012 0.108376 0.105408 0.077 Uiso 1 1 calc R U . . .
H16C H 0.780487 -0.007276 0.119864 0.077 Uiso 1 1 calc R U . . .
C17 C 1.1441(6) 0.1772(3) 0.09608(11) 0.0450(8) Uani 1 1 d . . . . .
H17A H 1.286290 0.196460 0.110349 0.054 Uiso 1 1 calc R U . . .
H17B H 1.039182 0.233029 0.100297 0.054 Uiso 1 1 calc R U . . .
H17C H 1.162684 0.162805 0.060855 0.054 Uiso 1 1 calc R U . . .
C18 C 0.8088(4) 0.34391(17) 0.45214(9) 0.0165(5) Uani 1 1 d . . . . .
C19 C 0.6353(4) 0.40282(19) 0.47058(9) 0.0199(5) Uani 1 1 d . . . . .
H19 H 0.505114 0.409752 0.451468 0.024 Uiso 1 1 calc R U . . .
C20 C 0.6479(4) 0.4512(2) 0.51581(9) 0.0215(5) Uani 1 1 d . . . . .
H20 H 0.527277 0.490911 0.527024 0.026 Uiso 1 1 calc R U . . .
C21 C 0.8362(4) 0.44252(18) 0.54525(9) 0.0187(5) Uani 1 1 d . . . . .
C22 C 1.0095(4) 0.38212(18) 0.52720(9) 0.0196(5) Uani 1 1 d . . . . .
H22 H 1.138833 0.373938 0.546478 0.024 Uiso 1 1 calc R U . . .
C23 C 0.9946(4) 0.33465(19) 0.48204(9) 0.0187(5) Uani 1 1 d . . . . .
H23 H 1.114451 0.294393 0.470906 0.022 Uiso 1 1 calc R U . . .
C24 C 0.6980(5) 0.5720(2) 0.60180(12) 0.0353(7) Uani 1 1 d . . . . .
H24A H 0.548151 0.544602 0.602757 0.042 Uiso 1 1 calc R U . . .
H24B H 0.708069 0.623881 0.575962 0.042 Uiso 1 1 calc R U . . .
H24C H 0.733786 0.602506 0.633783 0.042 Uiso 1 1 calc R U . . .
C25 C 1.0724(5) 0.5057(2) 0.61103(10) 0.0290(6) Uani 1 1 d . . . . .
H25A H 1.163261 0.540940 0.586552 0.035 Uiso 1 1 calc R U . . .
H25B H 1.138580 0.439741 0.618802 0.035 Uiso 1 1 calc R U . . .
H25C H 1.063473 0.546845 0.641102 0.035 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.721(2) . ?
S1 C14 1.775(2) . ?
O1 C11 1.214(3) . ?
O2 C11 1.353(3) . ?
O2 C12 1.445(3) . ?
N1 C21 1.400(3) . ?
N1 C25 1.453(3) . ?
N1 C24 1.456(3) . ?
C1 C2 1.417(3) . ?
C1 C10 1.425(3) . ?
C1 C11 1.455(3) . ?
C2 C3 1.397(3) . ?
C3 C4 1.421(3) . ?
C3 C13 1.423(3) . ?
C4 C5 1.381(3) . ?
C4 C10 1.487(3) . ?
C5 C6 1.391(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(4) . ?
C8 C15 1.525(4) . ?
C9 C10 1.390(3) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.366(3) . ?
C13 H13 0.9500 . ?
C14 C18 1.460(3) . ?
C15 C17 1.518(4) . ?
C15 C16 1.518(5) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C23 1.395(3) . ?
C18 C19 1.401(3) . ?
C19 C20 1.384(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.407(4) . ?
C22 C23 1.378(3) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C14 91.05(12) . . ?
C11 O2 C12 116.02(19) . . ?
C21 N1 C25 117.2(2) . . ?
C21 N1 C24 117.5(2) . . ?
C25 N1 C24 114.7(2) . . ?
C2 C1 C10 106.6(2) . . ?
C2 C1 C11 125.6(2) . . ?
C10 C1 C11 127.5(2) . . ?
C3 C2 C1 111.2(2) . . ?
C3 C2 S1 111.49(18) . . ?
C1 C2 S1 137.2(2) . . ?
C2 C3 C4 108.0(2) . . ?
C2 C3 C13 113.4(2) . . ?
C4 C3 C13 138.5(2) . . ?
C5 C4 C3 125.1(2) . . ?
C5 C4 C10 128.3(2) . . ?
C3 C4 C10 106.6(2) . . ?
C4 C5 C6 128.1(3) . . ?
C4 C5 H5 116.0 . . ?
C6 C5 H5 116.0 . . ?
C7 C6 C5 129.0(3) . . ?
C7 C6 H6 115.5 . . ?
C5 C6 H6 115.5 . . ?
C6 C7 C8 131.4(2) . . ?
C6 C7 H7 114.3 . . ?
C8 C7 H7 114.3 . . ?
C7 C8 C9 126.2(2) . . ?
C7 C8 C15 115.8(2) . . ?
C9 C8 C15 117.9(2) . . ?
C10 C9 C8 130.0(2) . . ?
C10 C9 H9 115.0 . . ?
C8 C9 H9 115.0 . . ?
C9 C10 C1 125.4(2) . . ?
C9 C10 C4 127.0(2) . . ?
C1 C10 C4 107.5(2) . . ?
O1 C11 O2 122.9(2) . . ?
O1 C11 C1 127.0(2) . . ?
O2 C11 C1 110.1(2) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 112.2(2) . . ?
C14 C13 H13 123.9 . . ?
C3 C13 H13 123.9 . . ?
C13 C14 C18 128.7(2) . . ?
C13 C14 S1 111.74(18) . . ?
C18 C14 S1 119.37(18) . . ?
C17 C15 C16 111.1(3) . . ?
C17 C15 C8 110.1(2) . . ?
C16 C15 C8 113.7(3) . . ?
C17 C15 H15 107.2 . . ?
C16 C15 H15 107.2 . . ?
C8 C15 H15 107.2 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C23 C18 C19 116.7(2) . . ?
C23 C18 C14 120.7(2) . . ?
C19 C18 C14 122.5(2) . . ?
C20 C19 C18 122.0(2) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C21 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 N1 121.9(2) . . ?
C20 C21 C22 117.4(2) . . ?
N1 C21 C22 120.7(2) . . ?
C23 C22 C21 121.1(2) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C22 C23 C18 122.0(2) . . ?
C22 C23 H23 119.0 . . ?
C18 C23 H23 119.0 . . ?
N1 C24 H24A 109.5 . . ?
N1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C25 H25A 109.5 . . ?
N1 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N1 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
C10 C1 C2 C3 1.5(3) . . . . ?
C11 C1 C2 C3 -173.0(2) . . . . ?
C10 C1 C2 S1 177.1(2) . . . . ?
C11 C1 C2 S1 2.7(4) . . . . ?
C14 S1 C2 C3 3.13(18) . . . . ?
C14 S1 C2 C1 -172.5(3) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
S1 C2 C3 C4 -179.24(16) . . . . ?
C1 C2 C3 C13 174.2(2) . . . . ?
S1 C2 C3 C13 -2.7(3) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C13 C3 C4 C5 5.4(5) . . . . ?
C2 C3 C4 C10 2.3(3) . . . . ?
C13 C3 C4 C10 -172.9(3) . . . . ?
C3 C4 C5 C6 -177.0(3) . . . . ?
C10 C4 C5 C6 1.0(4) . . . . ?
C4 C5 C6 C7 1.5(5) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C6 C7 C8 C15 178.1(3) . . . . ?
C7 C8 C9 C10 1.9(4) . . . . ?
C15 C8 C9 C10 -176.1(2) . . . . ?
C8 C9 C10 C1 177.3(2) . . . . ?
C8 C9 C10 C4 -0.8(4) . . . . ?
C2 C1 C10 C9 -178.4(2) . . . . ?
C11 C1 C10 C9 -4.0(4) . . . . ?
C2 C1 C10 C4 0.0(3) . . . . ?
C11 C1 C10 C4 174.3(2) . . . . ?
C5 C4 C10 C9 -1.4(4) . . . . ?
C3 C4 C10 C9 176.9(2) . . . . ?
C5 C4 C10 C1 -179.8(2) . . . . ?
C3 C4 C10 C1 -1.4(3) . . . . ?
C12 O2 C11 O1 2.9(3) . . . . ?
C12 O2 C11 C1 -178.64(18) . . . . ?
C2 C1 C11 O1 171.3(2) . . . . ?
C10 C1 C11 O1 -2.0(4) . . . . ?
C2 C1 C11 O2 -7.1(3) . . . . ?
C10 C1 C11 O2 179.6(2) . . . . ?
C2 C3 C13 C14 0.4(3) . . . . ?
C4 C3 C13 C14 175.5(3) . . . . ?
C3 C13 C14 C18 -173.3(2) . . . . ?
C3 C13 C14 S1 2.0(3) . . . . ?
C2 S1 C14 C13 -2.95(19) . . . . ?
C2 S1 C14 C18 172.84(19) . . . . ?
C7 C8 C15 C17 -98.1(3) . . . . ?
C9 C8 C15 C17 80.0(3) . . . . ?
C7 C8 C15 C16 136.4(3) . . . . ?
C9 C8 C15 C16 -45.4(4) . . . . ?
C13 C14 C18 C23 4.6(4) . . . . ?
S1 C14 C18 C23 -170.34(18) . . . . ?
C13 C14 C18 C19 -178.0(2) . . . . ?
S1 C14 C18 C19 7.0(3) . . . . ?
C23 C18 C19 C20 1.1(4) . . . . ?
C14 C18 C19 C20 -176.3(2) . . . . ?
C18 C19 C20 C21 -0.4(4) . . . . ?
C19 C20 C21 N1 -179.7(2) . . . . ?
C19 C20 C21 C22 -0.6(4) . . . . ?
C25 N1 C21 C20 -159.8(3) . . . . ?
C24 N1 C21 C20 -17.1(4) . . . . ?
C25 N1 C21 C22 21.1(4) . . . . ?
C24 N1 C21 C22 163.9(3) . . . . ?
C20 C21 C22 C23 0.8(4) . . . . ?
N1 C21 C22 C23 179.9(2) . . . . ?
C21 C22 C23 C18 0.0(4) . . . . ?
C19 C18 C23 C22 -1.0(4) . . . . ?
C14 C18 C23 C22 176.6(2) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_shelxl_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1868703'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime University
Japan
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H30 O4 S, 0.258(H2 O)'
_chemical_formula_sum            'C32 H30.52 O4.26 S'
_chemical_formula_weight         515.30

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   13.9336(7)
_cell_length_b                   19.7182(9)
_cell_length_c                   20.3209(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.298(5)
_cell_angle_gamma                90
_cell_volume                     5433.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14523
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      30.37

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             2181
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.156
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.431
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            46281
_diffrn_reflns_av_unetI/netI     0.0719
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.823
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6557
_reflns_number_gt                4029
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.1164P)²+8.8350P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6557
_refine_ls_number_parameters     356
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1375
_refine_ls_R_factor_gt           0.0847
_refine_ls_wR_factor_ref         0.2401
_refine_ls_wR_factor_gt          0.2070
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 0.56105(6) 0.16841(4) 0.42216(4) 0.0324(2) Uani 1 1 d . . . . .
O1 O 0.85089(17) 0.19973(13) 0.33903(12) 0.0395(6) Uani 1 1 d . . . . .
O2 O 0.72869(18) 0.13290(12) 0.35844(13) 0.0439(6) Uani 1 1 d . . . . .
O3 O 0.09489(18) 0.09395(14) 0.46284(15) 0.0512(7) Uani 1 1 d . . . . .
O4 O 0.16480(19) 0.08879(15) 0.37400(14) 0.0537(7) Uani 1 1 d . . . . .
C1 C 0.7287(2) 0.24373(17) 0.39383(16) 0.0306(7) Uani 1 1 d . . . . .
C2 C 0.6427(2) 0.23274(16) 0.41964(16) 0.0312(7) Uani 1 1 d . . . . .
C3 C 0.6198(2) 0.29146(16) 0.45070(17) 0.0324(7) Uani 1 1 d . . . . .
C4 C 0.6889(3) 0.34195(17) 0.44677(17) 0.0341(8) Uani 1 1 d . . . . .
C5 C 0.6941(3) 0.40541(17) 0.47569(18) 0.0379(8) Uani 1 1 d . . . . .
H5 H 0.645291 0.415244 0.500164 0.046 Uiso 1 1 calc R U . . .
C6 C 0.7614(3) 0.45691(18) 0.4737(2) 0.0467(10) Uani 1 1 d . . . . .
H6 H 0.756529 0.495432 0.500791 0.056 Uiso 1 1 calc R U . . .
C7 C 0.8344(3) 0.46014(19) 0.4380(2) 0.0475(10) Uani 1 1 d . . . . .
H7 H 0.868736 0.502093 0.441852 0.057 Uiso 1 1 calc R U . . .
C8 C 0.8663(3) 0.41195(18) 0.39712(19) 0.0429(9) Uani 1 1 d . . . . .
C9 C 0.8320(3) 0.34484(17) 0.38705(17) 0.0353(8) Uani 1 1 d . . . . .
H9 H 0.865849 0.317767 0.361012 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7579(2) 0.31170(17) 0.40835(16) 0.0327(7) Uani 1 1 d . . . . .
C11 C 0.7768(2) 0.19271(17) 0.36109(17) 0.0332(7) Uani 1 1 d . . . . .
C12 C 0.7735(3) 0.0778(2) 0.3303(3) 0.0640(13) Uani 1 1 d . . . . .
H12A H 0.840616 0.070599 0.357328 0.077 Uiso 1 1 calc R U . . .
H12B H 0.775843 0.088720 0.283672 0.077 Uiso 1 1 calc R U . . .
H12C H 0.734547 0.036486 0.330766 0.077 Uiso 1 1 calc R U . . .
C13 C 0.5339(2) 0.28451(16) 0.47721(17) 0.0326(7) Uani 1 1 d . . . . .
H13 H 0.507983 0.319336 0.500413 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4937(2) 0.22109(16) 0.46482(16) 0.0301(7) Uani 1 1 d . . . . .
C15 C 0.9408(3) 0.4347(2) 0.3589(2) 0.0531(10) Uani 1 1 d . . . . .
H15 H 0.961959 0.393846 0.336710 0.064 Uiso 1 1 calc R U . . .
C16 C 1.0339(3) 0.4671(2) 0.4036(2) 0.0572(11) Uani 1 1 d . . . . .
H16A H 1.063326 0.435648 0.440090 0.069 Uiso 1 1 calc R U . . .
H16B H 1.016061 0.509370 0.423150 0.069 Uiso 1 1 calc R U . . .
H16C H 1.081607 0.476736 0.376162 0.069 Uiso 1 1 calc R U . . .
C17 C 0.8906(4) 0.4837(3) 0.3027(3) 0.0802(17) Uani 1 1 d . . . . .
H17A H 0.875584 0.526395 0.322878 0.096 Uiso 1 1 calc R U . . .
H17B H 0.829280 0.463359 0.276767 0.096 Uiso 1 1 calc R U . . .
H17C H 0.934817 0.492610 0.272512 0.096 Uiso 1 1 calc R U . . .
C18 C 0.4035(2) 0.19426(17) 0.48115(17) 0.0336(7) Uani 1 1 d . . . . .
C19 C 0.3304(2) 0.15776(16) 0.43785(18) 0.0338(8) Uani 1 1 d . . . . .
H19 H 0.331420 0.145288 0.392855 0.041 Uiso 1 1 calc R U . . .
C20 C 0.2540(2) 0.14182(17) 0.47065(19) 0.0356(8) Uani 1 1 d . . . . .
C21 C 0.2783(2) 0.16754(16) 0.53730(18) 0.0350(8) Uani 1 1 d . . . . .
C22 C 0.2248(3) 0.15950(18) 0.5867(2) 0.0416(9) Uani 1 1 d . . . . .
H22 H 0.164188 0.135815 0.572638 0.050 Uiso 1 1 calc R U . . .
C23 C 0.2474(3) 0.1813(2) 0.6544(2) 0.0473(10) Uani 1 1 d . . . . .
C24 C 0.3302(3) 0.2203(2) 0.6866(2) 0.0502(10) Uani 1 1 d . . . . .
H24 H 0.332340 0.232267 0.732190 0.060 Uiso 1 1 calc R U . . .
C25 C 0.4070(3) 0.2432(2) 0.66218(19) 0.0486(10) Uani 1 1 d . . . . .
H25 H 0.453850 0.269180 0.693542 0.058 Uiso 1 1 calc R U . . .
C26 C 0.4293(3) 0.23540(18) 0.59946(19) 0.0417(9) Uani 1 1 d . . . . .
H26 H 0.489271 0.255418 0.594629 0.050 Uiso 1 1 calc R U . . .
C27 C 0.3758(2) 0.20255(17) 0.54375(18) 0.0359(8) Uani 1 1 d . . . . .
C28 C 0.1644(3) 0.10715(18) 0.4381(2) 0.0401(8) Uani 1 1 d . . . . .
C29 C 0.0771(3) 0.0532(3) 0.3383(3) 0.0780(16) Uani 1 1 d . . . . .
H29A H 0.020157 0.083659 0.331674 0.094 Uiso 1 1 calc R U . . .
H29B H 0.065686 0.013720 0.364807 0.094 Uiso 1 1 calc R U . . .
H29C H 0.086243 0.038026 0.294173 0.094 Uiso 1 1 calc R U . . .
C30 C 0.1785(3) 0.1647(2) 0.7000(2) 0.0607(12) Uani 1 1 d . . . . .
H30 H 0.221844 0.151993 0.744702 0.073 Uiso 1 1 calc R U . . .
C31 C 0.1109(4) 0.1060(3) 0.6791(3) 0.0704(14) Uani 1 1 d . . . . .
H31A H 0.147352 0.068561 0.664483 0.085 Uiso 1 1 calc R U . . .
H31B H 0.056527 0.119631 0.641614 0.085 Uiso 1 1 calc R U . . .
H31C H 0.084342 0.091225 0.717399 0.085 Uiso 1 1 calc R U . . .
C32 C 0.1206(3) 0.2276(3) 0.7133(2) 0.0605(12) Uani 1 1 d . . . . .
H32A H 0.085493 0.217367 0.748665 0.073 Uiso 1 1 calc R U . . .
H32B H 0.073032 0.240308 0.671617 0.073 Uiso 1 1 calc R U . . .
H32C H 0.166473 0.265254 0.727927 0.073 Uiso 1 1 calc R U . . .
O5 O -0.0552(9) -0.0041(8) 0.4449(7) 0.074(5) Uani 0.258(9) 1 d D . P A -1
H5OA H -0.058(13) -0.028(8) 0.479(6) 0.089 Uiso 0.258(9) 1 d D U P A -1
H5OB H -0.002(7) 0.017(8) 0.457(9) 0.089 Uiso 0.258(9) 1 d D U P A -1


_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 C2 1.713(3) . ?
S1 C14 1.756(3) . ?
O1 C11 1.224(4) . ?
O2 C11 1.351(4) . ?
O2 C12 1.435(4) . ?
O3 C28 1.218(4) . ?
O4 C28 1.353(5) . ?
O4 C29 1.451(5) . ?
C1 C10 1.412(5) . ?
C1 C2 1.430(5) . ?
C1 C11 1.452(5) . ?
C2 C3 1.391(4) . ?
C3 C4 1.400(5) . ?
C3 C13 1.428(5) . ?
C4 C5 1.377(5) . ?
C4 C10 1.495(5) . ?
C5 C6 1.390(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.401(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(5) . ?
C8 C15 1.500(6) . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9500 . ?
C14 C18 1.470(5) . ?
C15 C17 1.536(6) . ?
C15 C16 1.542(6) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.385(5) . ?
C18 C27 1.422(5) . ?
C19 C20 1.415(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.412(5) . ?
C20 C28 1.444(5) . ?
C21 C22 1.390(5) . ?
C21 C27 1.502(5) . ?
C22 C23 1.406(5) . ?
C22 H22 0.9500 . ?
C23 C24 1.416(6) . ?
C23 C30 1.516(5) . ?
C24 C25 1.356(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.388(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.367(5) . ?
C26 H26 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 C31 1.491(7) . ?
C30 C32 1.537(6) . ?
C30 H30 1.0000 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
O5 H5OA 0.841(10) . ?
O5 H5OB 0.841(10) . ?

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 S1 C14 90.63(16) . . ?
C11 O2 C12 114.8(3) . . ?
C28 O4 C29 114.9(3) . . ?
C10 C1 C2 107.0(3) . . ?
C10 C1 C11 127.8(3) . . ?
C2 C1 C11 125.2(3) . . ?
C3 C2 C1 109.8(3) . . ?
C3 C2 S1 112.3(3) . . ?
C1 C2 S1 137.9(3) . . ?
C2 C3 C4 109.5(3) . . ?
C2 C3 C13 113.0(3) . . ?
C4 C3 C13 137.5(3) . . ?
C5 C4 C3 126.2(3) . . ?
C5 C4 C10 127.5(3) . . ?
C3 C4 C10 106.2(3) . . ?
C4 C5 C6 128.4(4) . . ?
C4 C5 H5 115.8 . . ?
C6 C5 H5 115.8 . . ?
C7 C6 C5 129.3(4) . . ?
C7 C6 H6 115.3 . . ?
C5 C6 H6 115.3 . . ?
C6 C7 C8 130.8(4) . . ?
C6 C7 H7 114.6 . . ?
C8 C7 H7 114.6 . . ?
C7 C8 C9 125.5(4) . . ?
C7 C8 C15 117.2(3) . . ?
C9 C8 C15 117.3(4) . . ?
C10 C9 C8 131.1(4) . . ?
C10 C9 H9 114.4 . . ?
C8 C9 H9 114.4 . . ?
C9 C10 C1 126.0(3) . . ?
C9 C10 C4 126.5(3) . . ?
C1 C10 C4 107.4(3) . . ?
O1 C11 O2 122.4(3) . . ?
O1 C11 C1 127.3(3) . . ?
O2 C11 C1 110.2(3) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 111.2(3) . . ?
C14 C13 H13 124.4 . . ?
C3 C13 H13 124.4 . . ?
C13 C14 C18 128.4(3) . . ?
C13 C14 S1 112.9(2) . . ?
C18 C14 S1 118.7(2) . . ?
C8 C15 C17 108.8(4) . . ?
C8 C15 C16 114.0(4) . . ?
C17 C15 C16 110.9(4) . . ?
C8 C15 H15 107.7 . . ?
C17 C15 H15 107.7 . . ?
C16 C15 H15 107.7 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C27 108.5(3) . . ?
C19 C18 C14 125.9(3) . . ?
C27 C18 C14 125.7(3) . . ?
C18 C19 C20 109.8(3) . . ?
C18 C19 H19 125.1 . . ?
C20 C19 H19 125.1 . . ?
C21 C20 C19 109.4(3) . . ?
C21 C20 C28 126.9(3) . . ?
C19 C20 C28 123.7(3) . . ?
C22 C21 C20 126.9(3) . . ?
C22 C21 C27 127.9(3) . . ?
C20 C21 C27 105.1(3) . . ?
C21 C22 C23 129.4(4) . . ?
C21 C22 H22 115.3 . . ?
C23 C22 H22 115.3 . . ?
C22 C23 C24 126.4(4) . . ?
C22 C23 C30 120.1(4) . . ?
C24 C23 C30 113.5(4) . . ?
C25 C24 C23 129.8(4) . . ?
C25 C24 H24 115.1 . . ?
C23 C24 H24 115.1 . . ?
C24 C25 C26 131.3(4) . . ?
C24 C25 H25 114.3 . . ?
C26 C25 H25 114.3 . . ?
C27 C26 C25 128.2(4) . . ?
C27 C26 H26 115.9 . . ?
C25 C26 H26 115.9 . . ?
C26 C27 C18 125.9(3) . . ?
C26 C27 C21 126.9(3) . . ?
C18 C27 C21 107.2(3) . . ?
O3 C28 O4 121.3(3) . . ?
O3 C28 C20 126.8(4) . . ?
O4 C28 C20 111.9(3) . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C31 C30 C23 116.2(4) . . ?
C31 C30 C32 110.7(4) . . ?
C23 C30 C32 111.4(4) . . ?
C31 C30 H30 105.9 . . ?
C23 C30 H30 105.9 . . ?
C32 C30 H30 105.9 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
H5OA O5 H5OB 104.5(17) . . ?

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
C10 C1 C2 C3 -1.3(4) . . . . ?
C11 C1 C2 C3 176.9(3) . . . . ?
C10 C1 C2 S1 178.1(3) . . . . ?
C11 C1 C2 S1 -3.7(6) . . . . ?
C14 S1 C2 C3 0.6(3) . . . . ?
C14 S1 C2 C1 -178.7(4) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
S1 C2 C3 C4 -179.8(2) . . . . ?
C1 C2 C3 C13 179.4(3) . . . . ?
S1 C2 C3 C13 -0.1(4) . . . . ?
C2 C3 C4 C5 -175.5(3) . . . . ?
C13 C3 C4 C5 4.9(7) . . . . ?
C2 C3 C4 C10 1.7(4) . . . . ?
C13 C3 C4 C10 -178.0(4) . . . . ?
C3 C4 C5 C6 179.5(4) . . . . ?
C10 C4 C5 C6 2.9(6) . . . . ?
C4 C5 C6 C7 6.1(7) . . . . ?
C5 C6 C7 C8 -4.4(7) . . . . ?
C6 C7 C8 C9 -4.4(7) . . . . ?
C6 C7 C8 C15 173.2(4) . . . . ?
C7 C8 C9 C10 5.5(6) . . . . ?
C15 C8 C9 C10 -172.1(4) . . . . ?
C8 C9 C10 C1 178.8(3) . . . . ?
C8 C9 C10 C4 3.4(6) . . . . ?
C2 C1 C10 C9 -173.9(3) . . . . ?
C11 C1 C10 C9 8.0(6) . . . . ?
C2 C1 C10 C4 2.2(4) . . . . ?
C11 C1 C10 C4 -175.9(3) . . . . ?
C5 C4 C10 C9 -9.3(6) . . . . ?
C3 C4 C10 C9 173.6(3) . . . . ?
C5 C4 C10 C1 174.7(3) . . . . ?
C3 C4 C10 C1 -2.4(4) . . . . ?
C12 O2 C11 O1 2.4(5) . . . . ?
C12 O2 C11 C1 -176.7(3) . . . . ?
C10 C1 C11 O1 -1.3(6) . . . . ?
C2 C1 C11 O1 -179.1(3) . . . . ?
C10 C1 C11 O2 177.7(3) . . . . ?
C2 C1 C11 O2 -0.1(5) . . . . ?
C2 C3 C13 C14 -0.7(4) . . . . ?
C4 C3 C13 C14 179.0(4) . . . . ?
C3 C13 C14 C18 -177.4(3) . . . . ?
C3 C13 C14 S1 1.1(4) . . . . ?
C2 S1 C14 C13 -1.0(3) . . . . ?
C2 S1 C14 C18 177.6(3) . . . . ?
C7 C8 C15 C17 -70.2(5) . . . . ?
C9 C8 C15 C17 107.6(4) . . . . ?
C7 C8 C15 C16 54.1(5) . . . . ?
C9 C8 C15 C16 -128.1(4) . . . . ?
C13 C14 C18 C19 133.5(4) . . . . ?
S1 C14 C18 C19 -44.9(4) . . . . ?
C13 C14 C18 C27 -45.2(5) . . . . ?
S1 C14 C18 C27 136.4(3) . . . . ?
C27 C18 C19 C20 0.2(4) . . . . ?
C14 C18 C19 C20 -178.7(3) . . . . ?
C18 C19 C20 C21 -0.9(4) . . . . ?
C18 C19 C20 C28 176.6(3) . . . . ?
C19 C20 C21 C22 -176.5(3) . . . . ?
C28 C20 C21 C22 6.1(6) . . . . ?
C19 C20 C21 C27 1.2(4) . . . . ?
C28 C20 C21 C27 -176.2(3) . . . . ?
C20 C21 C22 C23 176.9(3) . . . . ?
C27 C21 C22 C23 -0.3(6) . . . . ?
C21 C22 C23 C24 3.4(6) . . . . ?
C21 C22 C23 C30 -178.1(4) . . . . ?
C22 C23 C24 C25 -2.7(7) . . . . ?
C30 C23 C24 C25 178.7(4) . . . . ?
C23 C24 C25 C26 -0.8(8) . . . . ?
C24 C25 C26 C27 1.7(7) . . . . ?
C25 C26 C27 C18 -177.9(4) . . . . ?
C25 C26 C27 C21 0.8(6) . . . . ?
C19 C18 C27 C26 179.5(3) . . . . ?
C14 C18 C27 C26 -1.6(6) . . . . ?
C19 C18 C27 C21 0.5(4) . . . . ?
C14 C18 C27 C21 179.4(3) . . . . ?
C22 C21 C27 C26 -2.3(6) . . . . ?
C20 C21 C27 C26 180.0(3) . . . . ?
C22 C21 C27 C18 176.7(3) . . . . ?
C20 C21 C27 C18 -1.0(3) . . . . ?
C29 O4 C28 O3 0.3(6) . . . . ?
C29 O4 C28 C20 179.5(4) . . . . ?
C21 C20 C28 O3 -0.5(6) . . . . ?
C19 C20 C28 O3 -177.5(3) . . . . ?
C21 C20 C28 O4 -179.7(3) . . . . ?
C19 C20 C28 O4 3.2(5) . . . . ?
C22 C23 C30 C31 21.6(6) . . . . ?
C24 C23 C30 C31 -159.7(4) . . . . ?
C22 C23 C30 C32 -106.4(4) . . . . ?
C24 C23 C30 C32 72.3(5) . . . . ?

_refine_diff_density_max         1.297
_refine_diff_density_min         -0.376
_refine_diff_density_rms         0.079



####################################################################### 
# 
# 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_shelxl_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1868702'
loop_
_audit_author_name
_audit_author_address
'Shigeki Mori'
;Ehime University
Japan
;
_audit_update_record             
;
2018-09-20 deposited with the CCDC.	2019-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H24 Fe O2 S'
_chemical_formula_sum            'C27 H24 Fe O2 S'
_chemical_formula_weight         468.37

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'
Fe Fe 0.3463 0.8444 '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'

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

_cell_length_a                   28.3482(11)
_cell_length_b                   19.5347(7)
_cell_length_c                   7.5873(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4201.6(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    17177
_cell_measurement_theta_min      2.07
_cell_measurement_theta_max      31.15

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.481
_exptl_crystal_F_000             1952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.840
_shelx_estimated_absorpt_T_min   0.787
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.494
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_measurement_device_type  'Rigaku Varimax with Saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            67743
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_av_R_equivalents  0.1390
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.775
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5064
_reflns_number_gt                3779
_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       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3.1 (Rigaku, 2018)'
_computing_publication_material  'CrystalStructure 4.3.1 (Rigaku, 2018)'
_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)+(0.0394P)²+3.9421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5064
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0497
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0928
_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
Fe1 Fe 0.41868(2) 0.39596(2) 0.61059(5) 0.01130(10) Uani 1 1 d . . . . .
S1 S 0.31933(2) 0.25470(3) 0.57014(9) 0.01164(14) Uani 1 1 d . . . . .
O1 O 0.22338(6) 0.06643(9) 0.7321(3) 0.0187(4) Uani 1 1 d . . . . .
O2 O 0.28990(6) 0.10937(9) 0.6133(3) 0.0155(4) Uani 1 1 d . . . . .
C1 C 0.23610(9) 0.18760(12) 0.7176(3) 0.0111(5) Uani 1 1 d . . . . .
C2 C 0.26543(9) 0.24338(13) 0.6678(3) 0.0111(5) Uani 1 1 d . . . . .
C3 C 0.24405(9) 0.30608(12) 0.7117(3) 0.0115(5) Uani 1 1 d . . . . .
C4 C 0.19970(9) 0.29162(13) 0.7883(3) 0.0124(5) Uani 1 1 d . . . . .
C5 C 0.16780(9) 0.33918(13) 0.8488(3) 0.0141(6) Uani 1 1 d . . . . .
H5 H 0.177558 0.385638 0.842097 0.017 Uiso 1 1 calc R U . . .
C6 C 0.12300(9) 0.32793(13) 0.9186(4) 0.0168(6) Uani 1 1 d . . . . .
H6 H 0.106021 0.368071 0.949835 0.020 Uiso 1 1 calc R U . . .
C7 C 0.09956(9) 0.26680(13) 0.9492(4) 0.0159(6) Uani 1 1 d . . . . .
H7 H 0.068761 0.271866 0.996811 0.019 Uiso 1 1 calc R U . . .
C8 C 0.11360(9) 0.19852(12) 0.9219(3) 0.0118(5) Uani 1 1 d . . . . .
C9 C 0.15640(9) 0.17736(13) 0.8533(3) 0.0128(5) Uani 1 1 d . . . . .
H9 H 0.160359 0.129139 0.846648 0.015 Uiso 1 1 calc R U . . .
C10 C 0.19474(9) 0.21556(13) 0.7922(3) 0.0127(5) Uani 1 1 d . . . . .
C11 C 0.24737(9) 0.11560(13) 0.6918(3) 0.0120(5) Uani 1 1 d . . . . .
C12 C 0.30545(10) 0.04024(13) 0.5817(4) 0.0219(7) Uani 1 1 d . . . . .
H12A H 0.281796 0.016076 0.510928 0.026 Uiso 1 1 calc R U . . .
H12B H 0.309585 0.016578 0.694520 0.026 Uiso 1 1 calc R U . . .
H12C H 0.335531 0.041031 0.518091 0.026 Uiso 1 1 calc R U . . .
C13 C 0.27235(9) 0.36353(13) 0.6629(3) 0.0131(5) Uani 1 1 d . . . . .
H13 H 0.263355 0.409737 0.682817 0.016 Uiso 1 1 calc R U . . .
C14 C 0.31358(9) 0.34489(12) 0.5849(3) 0.0121(5) Uani 1 1 d . . . . .
C15 C 0.07627(9) 0.14534(13) 0.9719(4) 0.0151(6) Uani 1 1 d . . . . .
H15 H 0.060378 0.162155 1.081319 0.018 Uiso 1 1 calc R U . . .
C16 C 0.03841(9) 0.14063(14) 0.8283(4) 0.0202(6) Uani 1 1 d . . . . .
H16A H 0.052240 0.121136 0.721109 0.024 Uiso 1 1 calc R U . . .
H16B H 0.026168 0.186493 0.802864 0.024 Uiso 1 1 calc R U . . .
H16C H 0.012607 0.111251 0.869140 0.024 Uiso 1 1 calc R U . . .
C17 C 0.09515(10) 0.07434(13) 1.0116(4) 0.0187(6) Uani 1 1 d . . . . .
H17A H 0.120947 0.077714 1.097143 0.022 Uiso 1 1 calc R U . . .
H17B H 0.106873 0.053430 0.902683 0.022 Uiso 1 1 calc R U . . .
H17C H 0.069817 0.046009 1.060653 0.022 Uiso 1 1 calc R U . . .
C18 C 0.35095(9) 0.38809(12) 0.5151(4) 0.0126(5) Uani 1 1 d . . . . .
C19 C 0.38463(9) 0.37001(14) 0.3830(4) 0.0139(5) Uani 1 1 d . . . . .
H19 H 0.3858(10) 0.3321(15) 0.325(4) 0.017 Uiso 1 1 d . U . . .
C20 C 0.41512(10) 0.42684(14) 0.3543(4) 0.0163(6) Uani 1 1 d . . . . .
H20 H 0.4413(10) 0.4271(14) 0.271(4) 0.020 Uiso 1 1 d . U . . .
C21 C 0.40023(10) 0.48026(14) 0.4679(4) 0.0178(6) Uani 1 1 d . . . . .
H21 H 0.4164(10) 0.5228(15) 0.480(4) 0.021 Uiso 1 1 d . U . . .
C22 C 0.36081(9) 0.45694(13) 0.5674(4) 0.0143(6) Uani 1 1 d . . . . .
H22 H 0.3451(10) 0.4803(14) 0.650(4) 0.017 Uiso 1 1 d . U . . .
C23 C 0.42530(10) 0.32928(15) 0.8166(4) 0.0228(7) Uani 1 1 d . . . . .
H23 H 0.4004(11) 0.3018(16) 0.858(4) 0.027 Uiso 1 1 d . U . . .
C24 C 0.45874(11) 0.31393(15) 0.6840(4) 0.0248(7) Uani 1 1 d . . . . .
H24 H 0.4595(11) 0.2751(17) 0.622(4) 0.030 Uiso 1 1 d . U . . .
C25 C 0.48739(10) 0.37237(17) 0.6606(4) 0.0255(7) Uani 1 1 d . . . . .
H25 H 0.5099(12) 0.3789(16) 0.587(4) 0.031 Uiso 1 1 d . U . . .
C26 C 0.47164(11) 0.42381(16) 0.7775(4) 0.0238(7) Uani 1 1 d . . . . .
H26 H 0.4838(11) 0.4704(16) 0.790(4) 0.029 Uiso 1 1 d . U . . .
C27 C 0.43328(10) 0.39679(16) 0.8748(4) 0.0219(6) Uani 1 1 d . . . . .
H27 H 0.4155(11) 0.4211(16) 0.949(4) 0.026 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Fe1 C25 2.037(3) . ?
Fe1 C26 2.038(3) . ?
Fe1 C20 2.038(3) . ?
Fe1 C21 2.039(3) . ?
Fe1 C24 2.042(3) . ?
Fe1 C19 2.042(3) . ?
Fe1 C23 2.043(3) . ?
Fe1 C27 2.047(3) . ?
Fe1 C22 2.054(3) . ?
Fe1 C18 2.058(3) . ?
S1 C2 1.712(3) . ?
S1 C14 1.773(2) . ?
O1 C11 1.216(3) . ?
O2 C11 1.350(3) . ?
O2 C12 1.441(3) . ?
C1 C10 1.412(4) . ?
C1 C2 1.422(3) . ?
C1 C11 1.455(3) . ?
C2 C3 1.407(3) . ?
C3 C4 1.414(4) . ?
C3 C13 1.428(4) . ?
C4 C5 1.375(4) . ?
C4 C10 1.493(3) . ?
C5 C6 1.394(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.386(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.407(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.383(4) . ?
C8 C15 1.531(3) . ?
C9 C10 1.398(4) . ?
C9 H9 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.360(4) . ?
C13 H13 0.9500 . ?
C14 C18 1.454(3) . ?
C15 C17 1.517(4) . ?
C15 C16 1.532(4) . ?
C15 H15 1.0000 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.429(4) . ?
C18 C22 1.430(4) . ?
C19 C20 1.424(4) . ?
C19 H19 0.86(3) . ?
C20 C21 1.418(4) . ?
C20 H20 0.97(3) . ?
C21 C22 1.423(4) . ?
C21 H21 0.95(3) . ?
C22 H22 0.90(3) . ?
C23 C27 1.409(4) . ?
C23 C24 1.414(4) . ?
C23 H23 0.94(3) . ?
C24 C25 1.412(4) . ?
C24 H24 0.89(3) . ?
C25 C26 1.413(4) . ?
C25 H25 0.86(3) . ?
C26 C27 1.416(4) . ?
C26 H26 0.98(3) . ?
C27 H27 0.89(3) . ?

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
C25 Fe1 C26 40.57(13) . . ?
C25 Fe1 C20 106.98(12) . . ?
C26 Fe1 C20 123.39(12) . . ?
C25 Fe1 C21 121.80(12) . . ?
C26 Fe1 C21 107.65(12) . . ?
C20 Fe1 C21 40.70(11) . . ?
C25 Fe1 C24 40.52(13) . . ?
C26 Fe1 C24 68.30(13) . . ?
C20 Fe1 C24 121.35(13) . . ?
C21 Fe1 C24 157.16(13) . . ?
C25 Fe1 C19 123.59(12) . . ?
C26 Fe1 C19 160.03(12) . . ?
C20 Fe1 C19 40.84(11) . . ?
C21 Fe1 C19 68.31(11) . . ?
C24 Fe1 C19 107.39(12) . . ?
C25 Fe1 C23 68.01(12) . . ?
C26 Fe1 C23 68.11(12) . . ?
C20 Fe1 C23 157.36(12) . . ?
C21 Fe1 C23 160.83(13) . . ?
C24 Fe1 C23 40.51(13) . . ?
C19 Fe1 C23 122.14(12) . . ?
C25 Fe1 C27 68.04(13) . . ?
C26 Fe1 C27 40.57(12) . . ?
C20 Fe1 C27 160.37(12) . . ?
C21 Fe1 C27 124.43(12) . . ?
C24 Fe1 C27 68.07(13) . . ?
C19 Fe1 C27 157.76(12) . . ?
C23 Fe1 C27 40.30(12) . . ?
C25 Fe1 C22 157.62(12) . . ?
C26 Fe1 C22 122.19(12) . . ?
C20 Fe1 C22 68.68(11) . . ?
C21 Fe1 C22 40.69(11) . . ?
C24 Fe1 C22 160.59(12) . . ?
C19 Fe1 C22 68.37(11) . . ?
C23 Fe1 C22 124.42(12) . . ?
C27 Fe1 C22 108.26(12) . . ?
C25 Fe1 C18 160.17(12) . . ?
C26 Fe1 C18 157.82(12) . . ?
C20 Fe1 C18 68.89(11) . . ?
C21 Fe1 C18 68.53(10) . . ?
C24 Fe1 C18 123.80(11) . . ?
C19 Fe1 C18 40.77(10) . . ?
C23 Fe1 C18 107.90(11) . . ?
C27 Fe1 C18 122.28(11) . . ?
C22 Fe1 C18 40.70(10) . . ?
C2 S1 C14 91.09(12) . . ?
C11 O2 C12 115.5(2) . . ?
C10 C1 C2 107.2(2) . . ?
C10 C1 C11 127.6(2) . . ?
C2 C1 C11 125.2(2) . . ?
C3 C2 C1 110.6(2) . . ?
C3 C2 S1 112.00(19) . . ?
C1 C2 S1 137.4(2) . . ?
C2 C3 C4 107.9(2) . . ?
C2 C3 C13 112.4(2) . . ?
C4 C3 C13 139.7(2) . . ?
C5 C4 C3 125.9(2) . . ?
C5 C4 C10 127.1(2) . . ?
C3 C4 C10 106.9(2) . . ?
C4 C5 C6 128.3(2) . . ?
C4 C5 H5 115.9 . . ?
C6 C5 H5 115.9 . . ?
C7 C6 C5 129.5(2) . . ?
C7 C6 H6 115.2 . . ?
C5 C6 H6 115.2 . . ?
C6 C7 C8 131.0(2) . . ?
C6 C7 H7 114.5 . . ?
C8 C7 H7 114.5 . . ?
C9 C8 C7 125.9(2) . . ?
C9 C8 C15 119.8(2) . . ?
C7 C8 C15 114.3(2) . . ?
C8 C9 C10 130.3(2) . . ?
C8 C9 H9 114.8 . . ?
C10 C9 H9 114.8 . . ?
C9 C10 C1 124.9(2) . . ?
C9 C10 C4 127.7(2) . . ?
C1 C10 C4 107.4(2) . . ?
O1 C11 O2 122.6(2) . . ?
O1 C11 C1 127.4(2) . . ?
O2 C11 C1 110.0(2) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C3 112.7(2) . . ?
C14 C13 H13 123.7 . . ?
C3 C13 H13 123.7 . . ?
C13 C14 C18 129.0(2) . . ?
C13 C14 S1 111.88(19) . . ?
C18 C14 S1 119.13(19) . . ?
C17 C15 C8 115.2(2) . . ?
C17 C15 C16 109.5(2) . . ?
C8 C15 C16 110.4(2) . . ?
C17 C15 H15 107.1 . . ?
C8 C15 H15 107.1 . . ?
C16 C15 H15 107.1 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 C22 107.3(2) . . ?
C19 C18 C14 126.8(2) . . ?
C22 C18 C14 126.0(2) . . ?
C19 C18 Fe1 69.02(15) . . ?
C22 C18 Fe1 69.49(14) . . ?
C14 C18 Fe1 126.48(18) . . ?
C20 C19 C18 108.7(2) . . ?
C20 C19 Fe1 69.43(15) . . ?
C18 C19 Fe1 70.21(15) . . ?
C20 C19 H19 125(2) . . ?
C18 C19 H19 127(2) . . ?
Fe1 C19 H19 129(2) . . ?
C21 C20 C19 107.5(2) . . ?
C21 C20 Fe1 69.67(16) . . ?
C19 C20 Fe1 69.74(15) . . ?
C21 C20 H20 128.1(17) . . ?
C19 C20 H20 124.5(17) . . ?
Fe1 C20 H20 125.5(17) . . ?
C20 C21 C22 108.7(2) . . ?
C20 C21 Fe1 69.63(15) . . ?
C22 C21 Fe1 70.22(15) . . ?
C20 C21 H21 123.9(18) . . ?
C22 C21 H21 127.2(18) . . ?
Fe1 C21 H21 122.0(18) . . ?
C21 C22 C18 107.9(2) . . ?
C21 C22 Fe1 69.09(15) . . ?
C18 C22 Fe1 69.81(14) . . ?
C21 C22 H22 126.8(18) . . ?
C18 C22 H22 125.3(18) . . ?
Fe1 C22 H22 125.4(19) . . ?
C27 C23 C24 108.3(3) . . ?
C27 C23 Fe1 70.00(16) . . ?
C24 C23 Fe1 69.68(17) . . ?
C27 C23 H23 123.3(19) . . ?
C24 C23 H23 128.4(19) . . ?
Fe1 C23 H23 123.5(19) . . ?
C25 C24 C23 107.7(3) . . ?
C25 C24 Fe1 69.57(16) . . ?
C23 C24 Fe1 69.81(16) . . ?
C25 C24 H24 127(2) . . ?
C23 C24 H24 125(2) . . ?
Fe1 C24 H24 123(2) . . ?
C24 C25 C26 108.3(3) . . ?
C24 C25 Fe1 69.91(17) . . ?
C26 C25 Fe1 69.75(17) . . ?
C24 C25 H25 129(2) . . ?
C26 C25 H25 123(2) . . ?
Fe1 C25 H25 124(2) . . ?
C25 C26 C27 107.7(3) . . ?
C25 C26 Fe1 69.68(17) . . ?
C27 C26 Fe1 70.07(17) . . ?
C25 C26 H26 127.7(19) . . ?
C27 C26 H26 124.6(19) . . ?
Fe1 C26 H26 124.5(19) . . ?
C23 C27 C26 108.0(3) . . ?
C23 C27 Fe1 69.69(17) . . ?
C26 C27 Fe1 69.36(17) . . ?
C23 C27 H27 127(2) . . ?
C26 C27 H27 124(2) . . ?
Fe1 C27 H27 120(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
C10 C1 C2 C3 1.0(3) . . . . ?
C11 C1 C2 C3 -179.9(2) . . . . ?
C10 C1 C2 S1 -179.2(2) . . . . ?
C11 C1 C2 S1 -0.1(5) . . . . ?
C14 S1 C2 C3 -0.6(2) . . . . ?
C14 S1 C2 C1 179.6(3) . . . . ?
C1 C2 C3 C4 -1.1(3) . . . . ?
S1 C2 C3 C4 179.03(18) . . . . ?
C1 C2 C3 C13 -179.7(2) . . . . ?
S1 C2 C3 C13 0.4(3) . . . . ?
C2 C3 C4 C5 -179.8(3) . . . . ?
C13 C3 C4 C5 -1.9(5) . . . . ?
C2 C3 C4 C10 0.8(3) . . . . ?
C13 C3 C4 C10 178.8(3) . . . . ?
C3 C4 C5 C6 177.2(3) . . . . ?
C10 C4 C5 C6 -3.6(5) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 C8 0.8(5) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C6 C7 C8 C15 -179.3(3) . . . . ?
C7 C8 C9 C10 -1.6(5) . . . . ?
C15 C8 C9 C10 177.2(3) . . . . ?
C8 C9 C10 C1 -177.1(3) . . . . ?
C8 C9 C10 C4 1.2(5) . . . . ?
C2 C1 C10 C9 178.1(2) . . . . ?
C11 C1 C10 C9 -0.9(4) . . . . ?
C2 C1 C10 C4 -0.5(3) . . . . ?
C11 C1 C10 C4 -179.5(3) . . . . ?
C5 C4 C10 C9 1.9(5) . . . . ?
C3 C4 C10 C9 -178.7(3) . . . . ?
C5 C4 C10 C1 -179.5(3) . . . . ?
C3 C4 C10 C1 -0.2(3) . . . . ?
C12 O2 C11 O1 -0.7(4) . . . . ?
C12 O2 C11 C1 179.5(2) . . . . ?
C10 C1 C11 O1 -1.0(5) . . . . ?
C2 C1 C11 O1 -179.9(3) . . . . ?
C10 C1 C11 O2 178.9(2) . . . . ?
C2 C1 C11 O2 -0.1(4) . . . . ?
C2 C3 C13 C14 0.0(3) . . . . ?
C4 C3 C13 C14 -177.9(3) . . . . ?
C3 C13 C14 C18 178.9(3) . . . . ?
C3 C13 C14 S1 -0.5(3) . . . . ?
C2 S1 C14 C13 0.6(2) . . . . ?
C2 S1 C14 C18 -178.8(2) . . . . ?
C9 C8 C15 C17 23.6(4) . . . . ?
C7 C8 C15 C17 -157.5(2) . . . . ?
C9 C8 C15 C16 -101.0(3) . . . . ?
C7 C8 C15 C16 77.9(3) . . . . ?
C13 C14 C18 C19 -156.1(3) . . . . ?
S1 C14 C18 C19 23.2(4) . . . . ?
C13 C14 C18 C22 24.1(4) . . . . ?
S1 C14 C18 C22 -156.5(2) . . . . ?
C13 C14 C18 Fe1 114.0(3) . . . . ?
S1 C14 C18 Fe1 -66.6(3) . . . . ?
C22 C18 C19 C20 0.3(3) . . . . ?
C14 C18 C19 C20 -179.5(2) . . . . ?
Fe1 C18 C19 C20 -58.95(18) . . . . ?
C22 C18 C19 Fe1 59.20(18) . . . . ?
C14 C18 C19 Fe1 -120.6(3) . . . . ?
C18 C19 C20 C21 -0.3(3) . . . . ?
Fe1 C19 C20 C21 -59.70(19) . . . . ?
C18 C19 C20 Fe1 59.43(19) . . . . ?
C19 C20 C21 C22 0.2(3) . . . . ?
Fe1 C20 C21 C22 -59.56(19) . . . . ?
C19 C20 C21 Fe1 59.74(18) . . . . ?
C20 C21 C22 C18 0.0(3) . . . . ?
Fe1 C21 C22 C18 -59.22(18) . . . . ?
C20 C21 C22 Fe1 59.19(19) . . . . ?
C19 C18 C22 C21 -0.1(3) . . . . ?
C14 C18 C22 C21 179.6(2) . . . . ?
Fe1 C18 C22 C21 58.77(19) . . . . ?
C19 C18 C22 Fe1 -58.90(18) . . . . ?
C14 C18 C22 Fe1 120.9(3) . . . . ?
C27 C23 C24 C25 -0.1(3) . . . . ?
Fe1 C23 C24 C25 59.5(2) . . . . ?
C27 C23 C24 Fe1 -59.6(2) . . . . ?
C23 C24 C25 C26 -0.3(3) . . . . ?
Fe1 C24 C25 C26 59.4(2) . . . . ?
C23 C24 C25 Fe1 -59.7(2) . . . . ?
C24 C25 C26 C27 0.5(3) . . . . ?
Fe1 C25 C26 C27 60.0(2) . . . . ?
C24 C25 C26 Fe1 -59.5(2) . . . . ?
C24 C23 C27 C26 0.4(3) . . . . ?
Fe1 C23 C27 C26 -59.0(2) . . . . ?
C24 C23 C27 Fe1 59.4(2) . . . . ?
C25 C26 C27 C23 -0.5(3) . . . . ?
Fe1 C26 C27 C23 59.2(2) . . . . ?
C25 C26 C27 Fe1 -59.7(2) . . . . ?

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.087



