# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1810725'
_audit_update_record             
;
2017-12-12 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_audit_creation_date             2017-12-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 O3 S'
_chemical_formula_sum            'C17 H12 O3 S'
_chemical_formula_weight         296.33
_chemical_melting_point          ?
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2863(10)
_cell_length_b                   8.9590(11)
_cell_length_c                   10.6474(12)
_cell_angle_alpha                87.057(10)
_cell_angle_beta                 70.068(11)
_cell_angle_gamma                71.080(11)
_cell_volume                     701.38(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1218
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2880
_cell_measurement_theta_min      2.7460
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.237
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84063
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             308
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3371
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         2.039
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_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    -75.00 120.00   1.00    8.00    --   30.00  54.00 120.00  195
  2  ω    -75.00  26.00   1.00    8.00    --   30.00  54.00 240.00  101
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0189173000
_diffrn_orient_matrix_UB_12      -0.0576452000
_diffrn_orient_matrix_UB_13      0.0458235000
_diffrn_orient_matrix_UB_21      0.0295186000
_diffrn_orient_matrix_UB_22      0.0506177000
_diffrn_orient_matrix_UB_23      0.0295032000
_diffrn_orient_matrix_UB_31      -0.0897348000
_diffrn_orient_matrix_UB_32      0.0339207000
_diffrn_orient_matrix_UB_33      0.0455357000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1871
_reflns_number_total             2472
_reflns_odcompleteness_completeness 82.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.94
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2472
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      0.966
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1231
_refine_ls_wR_factor_ref         0.1570
_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 Aromatic/amide H refined with riding coordinates:
 C16(H16), C6(H6), C2(H2A), C14(H14), C13(H13), C5(H5), C3(H3), C4(H4)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
2.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
S1 S 0.49313(9) 0.21652(8) 0.53591(7) 0.0389(3) Uani 1 1 d . . . . .
O2 O 0.2136(3) 0.2811(2) 0.92482(18) 0.0427(5) Uani 1 1 d . . . . .
H2 H 0.130446 0.358301 0.967968 0.064 Uiso 1 1 calc GR . . . .
O3 O 0.0174(3) 0.5413(2) 0.84690(18) 0.0439(5) Uani 1 1 d . . . . .
O1 O 0.6801(3) 0.0184(3) 0.7156(3) 0.0651(7) Uani 1 1 d . . . . .
C9 C 0.2611(3) 0.3075(3) 0.7928(3) 0.0313(6) Uani 1 1 d . . . . .
C11 C 0.1935(3) 0.4921(3) 0.6159(3) 0.0315(6) Uani 1 1 d . . . . .
C1 C 0.4251(3) -0.0600(3) 0.8300(3) 0.0333(6) Uani 1 1 d . . . . .
C10 C 0.1498(3) 0.4543(3) 0.7560(3) 0.0307(6) Uani 1 1 d . . . . .
C8 C 0.4070(3) 0.1978(3) 0.7053(3) 0.0320(6) Uani 1 1 d . . . . .
C15 C 0.1108(4) 0.6738(3) 0.4519(3) 0.0367(7) Uani 1 1 d . . . . .
C7 C 0.5169(4) 0.0483(3) 0.7510(3) 0.0373(7) Uani 1 1 d . . . . .
C12 C 0.3434(4) 0.3939(3) 0.5124(3) 0.0328(6) Uani 1 1 d . . . . .
C16 C 0.0805(4) 0.6315(3) 0.5818(3) 0.0349(6) Uani 1 1 d . . . . .
H16 H -0.017885 0.697220 0.649738 0.042 Uiso 1 1 calc R . . . .
C6 C 0.5127(4) -0.1694(3) 0.9034(3) 0.0414(7) Uani 1 1 d . . . . .
H6 H 0.625453 -0.171409 0.903801 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2572(4) -0.0605(3) 0.8295(3) 0.0425(7) Uani 1 1 d . . . . .
H2A H 0.196615 0.012866 0.781966 0.051 Uiso 1 1 calc R . . . .
C14 C 0.2631(4) 0.5730(4) 0.3516(3) 0.0429(7) Uani 1 1 d . . . . .
H14 H 0.287144 0.599591 0.263053 0.051 Uiso 1 1 calc R . . . .
C13 C 0.3768(4) 0.4372(4) 0.3804(3) 0.0418(7) Uani 1 1 d . . . . .
H13 H 0.476469 0.373763 0.311881 0.050 Uiso 1 1 calc R . . . .
C17 C -0.0108(4) 0.8210(4) 0.4148(3) 0.0470(8) Uani 1 1 d . . . . .
H17A H -0.116961 0.867035 0.491572 0.071 Uiso 1 1 calc GR . . . .
H17B H -0.046256 0.794352 0.344285 0.071 Uiso 1 1 calc GR . . . .
H17C H 0.053439 0.895385 0.384910 0.071 Uiso 1 1 calc GR . . . .
C5 C 0.4329(5) -0.2741(4) 0.9750(3) 0.0522(9) Uani 1 1 d . . . . .
H5 H 0.490510 -0.344423 1.025904 0.063 Uiso 1 1 calc R . . . .
C3 C 0.1803(4) -0.1688(4) 0.8989(4) 0.0527(8) Uani 1 1 d . . . . .
H3 H 0.069580 -0.169947 0.896468 0.063 Uiso 1 1 calc R . . . .
C4 C 0.2687(5) -0.2763(4) 0.9725(3) 0.0537(9) Uani 1 1 d . . . . .
H4 H 0.217128 -0.349280 1.019743 0.064 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C8 1.721(3) . ?
S1 C12 1.737(3) . ?
O2 H2 0.8200 . ?
O2 C9 1.355(3) . ?
O3 C10 1.244(3) . ?
O1 C7 1.213(3) . ?
C9 C10 1.464(4) . ?
C9 C8 1.361(4) . ?
C11 C10 1.460(4) . ?
C11 C12 1.411(4) . ?
C11 C16 1.412(4) . ?
C1 C7 1.478(4) . ?
C1 C6 1.395(4) . ?
C1 C2 1.394(4) . ?
C8 C7 1.517(4) . ?
C15 C16 1.375(4) . ?
C15 C14 1.410(4) . ?
C15 C17 1.505(4) . ?
C12 C13 1.397(4) . ?
C16 H16 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.372(4) . ?
C2 H2A 0.9300 . ?
C2 C3 1.378(4) . ?
C14 H14 0.9300 . ?
C14 C13 1.370(4) . ?
C13 H13 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C5 H5 0.9300 . ?
C5 C4 1.377(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(4) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S1 C12 103.27(13) . . ?
C9 O2 H2 109.5 . . ?
O2 C9 C10 116.5(2) . . ?
O2 C9 C8 118.4(2) . . ?
C8 C9 C10 125.1(2) . . ?
C12 C11 C10 122.6(2) . . ?
C12 C11 C16 118.4(2) . . ?
C16 C11 C10 119.0(2) . . ?
C6 C1 C7 118.8(2) . . ?
C2 C1 C7 122.2(2) . . ?
C2 C1 C6 118.9(3) . . ?
O3 C10 C9 117.8(2) . . ?
O3 C10 C11 122.4(2) . . ?
C11 C10 C9 119.8(2) . . ?
C9 C8 S1 124.6(2) . . ?
C9 C8 C7 122.2(2) . . ?
C7 C8 S1 113.13(19) . . ?
C16 C15 C14 117.3(3) . . ?
C16 C15 C17 122.6(3) . . ?
C14 C15 C17 120.0(3) . . ?
O1 C7 C1 122.1(3) . . ?
O1 C7 C8 118.1(3) . . ?
C1 C7 C8 119.7(2) . . ?
C11 C12 S1 124.5(2) . . ?
C13 C12 S1 116.0(2) . . ?
C13 C12 C11 119.5(2) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 C11 122.4(3) . . ?
C15 C16 H16 118.8 . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C1 C2 H2A 119.7 . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 H2A 119.7 . . ?
C15 C14 H14 118.9 . . ?
C13 C14 C15 122.1(3) . . ?
C13 C14 H14 118.9 . . ?
C12 C13 H13 119.9 . . ?
C14 C13 C12 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(3) . . ?
C4 C5 H5 119.6 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?

_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 1.273
_oxdiff_exptl_absorpt_empirical_full_min 0.829
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_6
_database_code_depnum_ccdc_archive 'CCDC 1830227'
_audit_update_record             
;
2018-03-16 deposited with the CCDC.
2018-04-16 downloaded from the CCDC.
;
_audit_creation_date             2018-03-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H18 O4 S'
_chemical_formula_sum            'C25 H18 O4 S'
_chemical_formula_weight         414.45
_chemical_melting_point          ?
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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.2549(16)
_cell_length_b                   20.063(5)
_cell_length_c                   14.429(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.37(3)
_cell_angle_gamma                90
_cell_volume                     2059.0(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1187
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.8160
_cell_measurement_theta_min      2.4860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.01306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.7e (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             864
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0865
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9485
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.010
_diffrn_reflns_theta_max         25.010
_diffrn_reflns_theta_min         1.761
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -75.00 120.00   1.00   25.00    --   30.00  54.00 240.00  195
  2  ω    -75.00  30.00   1.00   25.00    --   30.00  54.00   0.00  105
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  
'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0151079000
_diffrn_orient_matrix_UB_12      -0.0213060000
_diffrn_orient_matrix_UB_13      0.0399475000
_diffrn_orient_matrix_UB_21      0.0120450000
_diffrn_orient_matrix_UB_22      0.0281939000
_diffrn_orient_matrix_UB_23      0.0303670000
_diffrn_orient_matrix_UB_31      -0.0977884000
_diffrn_orient_matrix_UB_32      0.0001018000
_diffrn_orient_matrix_UB_33      -0.0001412000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1843
_reflns_number_total             3640
_reflns_odcompleteness_completeness 86.09
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     32.90
_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 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.121
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3640
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1532
_refine_ls_R_factor_gt           0.0850
_refine_ls_restrained_S_all      1.121
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1909
_refine_ls_wR_factor_ref         0.2527
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00D(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C008(H008), C00H(H00H), C00I(H00I), C00J(H00J), C00L(H00L), C00M(H00M),
 C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T),
 C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00O(H00C,H00D,H00E)
;
_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
S001 S 0.36639(18) 0.35480(7) 0.24559(9) 0.0650(5) Uani 1 1 d . . . . .
O002 O 0.2210(4) 0.53127(14) 0.4572(2) 0.0541(8) Uani 1 1 d . . . . .
O003 O 0.1700(5) 0.54031(17) 0.6297(2) 0.0696(10) Uani 1 1 d . . . . .
O004 O 0.1782(5) 0.56468(17) 0.3058(3) 0.0725(11) Uani 1 1 d . . . . .
O005 O 0.0790(5) 0.4658(2) 0.1187(3) 0.1019(15) Uani 1 1 d . . . . .
C006 C 0.3355(6) 0.3989(2) 0.4123(3) 0.0485(11) Uani 1 1 d . . . . .
C007 C 0.2860(5) 0.4543(2) 0.3457(3) 0.0467(11) Uani 1 1 d . . . . .
C008 C 0.3392(6) 0.3956(2) 0.5114(3) 0.0499(11) Uani 1 1 d . . . . .
H008 H 0.311471 0.433127 0.543839 0.060 Uiso 1 1 calc R . . . .
C009 C 0.3817(6) 0.3410(2) 0.3660(3) 0.0504(11) Uani 1 1 d . . . . .
C00A C 0.2228(6) 0.5218(2) 0.3644(3) 0.0505(12) Uani 1 1 d . . . . .
C00B C 0.2966(6) 0.4364(2) 0.2557(3) 0.0544(12) Uani 1 1 d . . . . .
C00C C 0.1531(6) 0.5934(2) 0.5875(4) 0.0519(12) Uani 1 1 d . . . . .
C00D C 0.1622(6) 0.5956(2) 0.4836(3) 0.0536(12) Uani 1 1 d . . . . .
H00A H 0.039644 0.606532 0.446213 0.064 Uiso 1 1 calc R . . . .
H00B H 0.250991 0.629413 0.472563 0.064 Uiso 1 1 calc R . . . .
C00E C 0.3742(7) 0.5204(2) 0.1322(3) 0.0545(12) Uani 1 1 d . . . . .
C00F C 0.3843(6) 0.3363(2) 0.5588(3) 0.0529(12) Uani 1 1 d . . . . .
C00G C 0.1225(6) 0.6568(2) 0.6352(4) 0.0605(14) Uani 1 1 d . . . . .
C00H C 0.4284(7) 0.2794(2) 0.5107(4) 0.0609(13) Uani 1 1 d . . . . .
H00H H 0.458042 0.239753 0.543757 0.073 Uiso 1 1 calc R . . . .
C00I C 0.4282(7) 0.2816(2) 0.4142(4) 0.0591(13) Uani 1 1 d . . . . .
H00I H 0.458720 0.244046 0.382615 0.071 Uiso 1 1 calc R . . . .
C00J C 0.3180(8) 0.5573(2) 0.0497(4) 0.0644(13) Uani 1 1 d . . . . .
H00J H 0.193269 0.555900 0.018060 0.077 Uiso 1 1 calc R . . . .
C00K C 0.2379(7) 0.4761(3) 0.1641(4) 0.0660(14) Uani 1 1 d . . . . .
C00L C 0.5617(7) 0.5226(3) 0.1789(4) 0.0647(14) Uani 1 1 d . . . . .
H00L H 0.601284 0.498452 0.234233 0.078 Uiso 1 1 calc R . . . .
C00M C 0.6893(8) 0.5613(3) 0.1418(4) 0.0720(15) Uani 1 1 d . . . . .
H00M H 0.815067 0.562303 0.171917 0.086 Uiso 1 1 calc R . . . .
C00N C 0.4468(9) 0.5961(3) 0.0140(4) 0.0760(16) Uani 1 1 d . . . . .
H00N H 0.408634 0.620585 -0.041159 0.091 Uiso 1 1 calc R . . . .
C00O C 0.3873(8) 0.3313(2) 0.6653(4) 0.0741(16) Uani 1 1 d . . . . .
H00C H 0.507657 0.345473 0.699937 0.111 Uiso 1 1 calc GR . . . .
H00D H 0.365224 0.285930 0.681328 0.111 Uiso 1 1 calc GR . . . .
H00E H 0.290791 0.359291 0.681198 0.111 Uiso 1 1 calc GR . . . .
C00P C 0.1239(7) 0.6555(3) 0.7328(4) 0.0768(17) Uani 1 1 d . . . . .
H00P H 0.138185 0.615451 0.765874 0.092 Uiso 1 1 calc R . . . .
C00Q C 0.6301(9) 0.5981(3) 0.0607(5) 0.0810(17) Uani 1 1 d . . . . .
H00Q H 0.715824 0.624644 0.037517 0.097 Uiso 1 1 calc R . . . .
C00R C 0.0992(8) 0.7180(3) 0.5878(5) 0.0865(19) Uani 1 1 d . . . . .
H00R H 0.095892 0.719236 0.523015 0.104 Uiso 1 1 calc R . . . .
C00S C 0.0808(10) 0.7771(3) 0.6358(8) 0.120(3) Uani 1 1 d . . . . .
H00S H 0.065797 0.817331 0.603277 0.144 Uiso 1 1 calc R . . . .
C00T C 0.1038(9) 0.7147(5) 0.7790(6) 0.118(3) Uani 1 1 d . . . . .
H00T H 0.102705 0.713818 0.843296 0.142 Uiso 1 1 calc R . . . .
C00U C 0.0851(10) 0.7757(5) 0.7319(8) 0.126(4) Uani 1 1 d . . . . .
H00U H 0.075507 0.814976 0.764781 0.151 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
S001 C009 1.742(5) . ?
S001 C00B 1.728(5) . ?
O002 C00A 1.356(5) . ?
O002 C00D 1.434(5) . ?
O003 C00C 1.222(5) . ?
O004 C00A 1.205(5) . ?
O005 C00K 1.226(6) . ?
C006 C007 1.467(6) . ?
C006 C008 1.426(6) . ?
C006 C009 1.412(6) . ?
C007 C00A 1.472(6) . ?
C007 C00B 1.364(6) . ?
C008 H008 0.9300 . ?
C008 C00F 1.378(6) . ?
C009 C00I 1.387(6) . ?
C00B C00K 1.531(7) . ?
C00C C00D 1.514(6) . ?
C00C C00G 1.484(6) . ?
C00D H00A 0.9700 . ?
C00D H00B 0.9700 . ?
C00E C00J 1.393(6) . ?
C00E C00K 1.469(7) . ?
C00E C00L 1.395(7) . ?
C00F C00H 1.406(6) . ?
C00F C00O 1.536(6) . ?
C00G C00P 1.407(7) . ?
C00G C00R 1.400(8) . ?
C00H H00H 0.9300 . ?
C00H C00I 1.394(6) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00J C00N 1.391(7) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.393(7) . ?
C00M H00M 0.9300 . ?
C00M C00Q 1.379(7) . ?
C00N H00N 0.9300 . ?
C00N C00Q 1.367(8) . ?
C00O H00C 0.9600 . ?
C00O H00D 0.9600 . ?
C00O H00E 0.9600 . ?
C00P H00P 0.9300 . ?
C00P C00T 1.384(9) . ?
C00Q H00Q 0.9300 . ?
C00R H00R 0.9300 . ?
C00R C00S 1.392(8) . ?
C00S H00S 0.9300 . ?
C00S C00U 1.381(11) . ?
C00T H00T 0.9300 . ?
C00T C00U 1.392(11) . ?
C00U H00U 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C00B S001 C009 91.6(2) . . ?
C00A O002 C00D 116.8(3) . . ?
C008 C006 C007 130.2(4) . . ?
C009 C006 C007 111.3(4) . . ?
C009 C006 C008 118.4(4) . . ?
C006 C007 C00A 128.5(4) . . ?
C00B C007 C006 111.8(4) . . ?
C00B C007 C00A 119.7(4) . . ?
C006 C008 H008 120.2 . . ?
C00F C008 C006 119.6(4) . . ?
C00F C008 H008 120.2 . . ?
C006 C009 S001 111.5(3) . . ?
C00I C009 S001 126.7(4) . . ?
C00I C009 C006 121.8(5) . . ?
O002 C00A C007 111.9(4) . . ?
O004 C00A O002 122.7(4) . . ?
O004 C00A C007 125.4(4) . . ?
C007 C00B S001 113.8(4) . . ?
C007 C00B C00K 128.8(4) . . ?
C00K C00B S001 117.2(3) . . ?
O003 C00C C00D 120.0(4) . . ?
O003 C00C C00G 121.7(5) . . ?
C00G C00C C00D 118.3(4) . . ?
O002 C00D C00C 108.1(4) . . ?
O002 C00D H00A 110.1 . . ?
O002 C00D H00B 110.1 . . ?
C00C C00D H00A 110.1 . . ?
C00C C00D H00B 110.1 . . ?
H00A C00D H00B 108.4 . . ?
C00J C00E C00K 119.2(5) . . ?
C00J C00E C00L 119.3(5) . . ?
C00L C00E C00K 121.4(5) . . ?
C008 C00F C00H 120.7(5) . . ?
C008 C00F C00O 120.6(4) . . ?
C00H C00F C00O 118.7(4) . . ?
C00P C00G C00C 118.5(5) . . ?
C00R C00G C00C 122.6(5) . . ?
C00R C00G C00P 118.9(5) . . ?
C00F C00H H00H 119.6 . . ?
C00I C00H C00F 120.8(5) . . ?
C00I C00H H00H 119.6 . . ?
C009 C00I C00H 118.7(5) . . ?
C009 C00I H00I 120.6 . . ?
C00H C00I H00I 120.6 . . ?
C00E C00J H00J 119.7 . . ?
C00N C00J C00E 120.6(5) . . ?
C00N C00J H00J 119.7 . . ?
O005 C00K C00B 116.4(5) . . ?
O005 C00K C00E 123.7(5) . . ?
C00E C00K C00B 119.7(4) . . ?
C00E C00L H00L 120.3 . . ?
C00M C00L C00E 119.4(5) . . ?
C00M C00L H00L 120.3 . . ?
C00L C00M H00M 119.8 . . ?
C00Q C00M C00L 120.3(5) . . ?
C00Q C00M H00M 119.8 . . ?
C00J C00N H00N 120.2 . . ?
C00Q C00N C00J 119.5(6) . . ?
C00Q C00N H00N 120.2 . . ?
C00F C00O H00C 109.5 . . ?
C00F C00O H00D 109.5 . . ?
C00F C00O H00E 109.5 . . ?
H00C C00O H00D 109.5 . . ?
H00C C00O H00E 109.5 . . ?
H00D C00O H00E 109.5 . . ?
C00G C00P H00P 120.5 . . ?
C00T C00P C00G 119.0(7) . . ?
C00T C00P H00P 120.5 . . ?
C00M C00Q H00Q 119.6 . . ?
C00N C00Q C00M 120.9(6) . . ?
C00N C00Q H00Q 119.6 . . ?
C00G C00R H00R 119.4 . . ?
C00S C00R C00G 121.1(7) . . ?
C00S C00R H00R 119.4 . . ?
C00R C00S H00S 120.1 . . ?
C00U C00S C00R 119.8(9) . . ?
C00U C00S H00S 120.1 . . ?
C00P C00T H00T 119.0 . . ?
C00P C00T C00U 121.9(8) . . ?
C00U C00T H00T 119.0 . . ?
C00S C00U C00T 119.2(8) . . ?
C00S C00U H00U 120.4 . . ?
C00T C00U H00U 120.4 . . ?

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
S001 C009 C00I C00H -178.2(4) . . . . ?
S001 C00B C00K O005 79.3(6) . . . . ?
S001 C00B C00K C00E -97.0(5) . . . . ?
O003 C00C C00D O002 -9.1(6) . . . . ?
O003 C00C C00G C00P 3.6(7) . . . . ?
O003 C00C C00G C00R -178.7(5) . . . . ?
C006 C007 C00A O002 3.0(6) . . . . ?
C006 C007 C00A O004 -177.4(4) . . . . ?
C006 C007 C00B S001 -0.6(5) . . . . ?
C006 C007 C00B C00K 173.1(4) . . . . ?
C006 C008 C00F C00H 0.7(7) . . . . ?
C006 C008 C00F C00O -179.4(4) . . . . ?
C006 C009 C00I C00H 0.2(7) . . . . ?
C007 C006 C008 C00F 177.5(4) . . . . ?
C007 C006 C009 S001 0.4(4) . . . . ?
C007 C006 C009 C00I -178.2(4) . . . . ?
C007 C00B C00K O005 -94.2(7) . . . . ?
C007 C00B C00K C00E 89.5(6) . . . . ?
C008 C006 C007 C00A -1.3(7) . . . . ?
C008 C006 C007 C00B -178.6(4) . . . . ?
C008 C006 C009 S001 179.3(3) . . . . ?
C008 C006 C009 C00I 0.6(6) . . . . ?
C008 C00F C00H C00I 0.2(7) . . . . ?
C009 S001 C00B C007 0.7(4) . . . . ?
C009 S001 C00B C00K -173.7(4) . . . . ?
C009 C006 C007 C00A 177.4(4) . . . . ?
C009 C006 C007 C00B 0.1(5) . . . . ?
C009 C006 C008 C00F -1.1(6) . . . . ?
C00A O002 C00D C00C 174.8(3) . . . . ?
C00A C007 C00B S001 -178.2(3) . . . . ?
C00A C007 C00B C00K -4.5(7) . . . . ?
C00B S001 C009 C006 -0.7(3) . . . . ?
C00B S001 C009 C00I 177.9(4) . . . . ?
C00B C007 C00A O002 -179.9(4) . . . . ?
C00B C007 C00A O004 -0.3(7) . . . . ?
C00C C00G C00P C00T 177.2(4) . . . . ?
C00C C00G C00R C00S -176.5(5) . . . . ?
C00D O002 C00A O004 0.2(6) . . . . ?
C00D O002 C00A C007 179.8(3) . . . . ?
C00D C00C C00G C00P -176.7(4) . . . . ?
C00D C00C C00G C00R 1.0(6) . . . . ?
C00E C00J C00N C00Q -0.1(8) . . . . ?
C00E C00L C00M C00Q 1.2(8) . . . . ?
C00F C00H C00I C009 -0.7(7) . . . . ?
C00G C00C C00D O002 171.2(3) . . . . ?
C00G C00P C00T C00U -1.0(9) . . . . ?
C00G C00R C00S C00U -0.2(10) . . . . ?
C00J C00E C00K O005 5.2(8) . . . . ?
C00J C00E C00K C00B -178.8(4) . . . . ?
C00J C00E C00L C00M -0.3(7) . . . . ?
C00J C00N C00Q C00M 1.0(9) . . . . ?
C00K C00E C00J C00N -175.5(4) . . . . ?
C00K C00E C00L C00M 174.8(4) . . . . ?
C00L C00E C00J C00N -0.3(7) . . . . ?
C00L C00E C00K O005 -169.9(5) . . . . ?
C00L C00E C00K C00B 6.1(7) . . . . ?
C00L C00M C00Q C00N -1.6(8) . . . . ?
C00O C00F C00H C00I -179.7(4) . . . . ?
C00P C00G C00R C00S 1.1(8) . . . . ?
C00P C00T C00U C00S 1.9(11) . . . . ?
C00R C00G C00P C00T -0.5(7) . . . . ?
C00R C00S C00U C00T -1.3(11) . . . . ?

_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 37.438
_oxdiff_exptl_absorpt_empirical_full_min 0.489
