# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_zww_0m
_database_code_depnum_ccdc_archive 'CCDC 1536356'
_audit_update_record             
;
2017-03-07 deposited with the CCDC.
2017-08-28 downloaded from the CCDC.
;
_audit_creation_date             2017-03-07
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 O4 S'
_chemical_formula_sum            'C18 H16 O4 S'
_chemical_formula_weight         328.37
_chemical_absolute_configuration ad
_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 0.0030 0.0020 '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 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   9.7797(10)
_cell_length_b                   10.9021(11)
_cell_length_c                   14.8619(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1584.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6962
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.189
_cell_measurement_theta_min      2.317
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0704 before and 0.0409 after correction.
The Ratio of minimum to maximum transmission is 0.8338.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_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  0.0209
_diffrn_reflns_av_unetI/netI     0.0183
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12594
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.405
_diffrn_reflns_theta_min         2.317
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.959
_reflns_number_gt                3036
_reflns_number_total             3497
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    ?
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details 
;
 Flack x determined using 1169 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.020(18)
_refine_ls_extinction_coef       0.021(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3497
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.041
_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)+(0.0447P)²+0.2861P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0860
_refine_ls_wR_factor_ref         0.0919
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C9(H9)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.59290(8) 0.45365(9) 0.70344(5) 0.0697(3) Uani 1 1 d . . . . .
O1 O 0.6531(2) 0.2460(2) 0.58097(13) 0.0722(6) Uani 1 1 d . . . . .
O2 O 0.73512(18) 0.18379(19) 0.28045(11) 0.0576(5) Uani 1 1 d . . . . .
O3 O 0.5851(2) 0.10500(16) 0.17355(12) 0.0617(5) Uani 1 1 d . . . . .
O4 O 0.7843(2) 0.3270(2) 0.38186(13) 0.0746(7) Uani 1 1 d . . . . .
C1 C 0.5281(3) 0.4279(3) 0.59734(15) 0.0483(6) Uani 1 1 d . . . . .
C2 C 0.5708(3) 0.3185(3) 0.54874(15) 0.0500(6) Uani 1 1 d . . . . .
C3 C 0.5068(3) 0.2964(3) 0.45674(15) 0.0517(6) Uani 1 1 d . . . . .
H3A H 0.4128 0.2703 0.4648 0.062 Uiso 1 1 calc R . . . .
H3B H 0.5057 0.3730 0.4236 0.062 Uiso 1 1 calc R . . . .
C4 C 0.5820(3) 0.2006(2) 0.40171(15) 0.0484(6) Uani 1 1 d . . . . .
H4 H 0.6074 0.1334 0.4422 0.058 Uiso 1 1 calc R . . . .
C5 C 0.7105(3) 0.2465(3) 0.35719(16) 0.0519(6) Uani 1 1 d . . . . .
C6 C 0.6233(3) 0.0983(2) 0.26306(18) 0.0583(7) Uani 1 1 d . . . . .
H6 H 0.6487 0.0143 0.2797 0.070 Uiso 1 1 calc R . . . .
C7 C 0.4652(3) 0.1825(2) 0.16340(16) 0.0507(6) Uani 1 1 d . . . . .
H7 H 0.3869 0.1311 0.1471 0.061 Uiso 1 1 calc R . . . .
C8 C 0.4407(2) 0.2371(3) 0.25784(15) 0.0502(6) Uani 1 1 d . . . . .
H8A H 0.4832 0.3172 0.2633 0.060 Uiso 1 1 calc R . . . .
H8B H 0.3437 0.2448 0.2702 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5071(3) 0.1452(2) 0.32145(16) 0.0521(6) Uani 1 1 d . . . . .
H9 H 0.4441 0.0797 0.3393 0.062 Uiso 1 1 calc R . . . .
C10 C 0.4879(2) 0.2751(2) 0.09072(14) 0.0428(5) Uani 1 1 d . . . . .
C11 C 0.6065(3) 0.3432(2) 0.08659(16) 0.0477(5) Uani 1 1 d . . . . .
H11 H 0.6750 0.3307 0.1290 0.057 Uiso 1 1 calc R . . . .
C12 C 0.6242(3) 0.4307(2) 0.01949(18) 0.0568(7) Uani 1 1 d . . . . .
H12 H 0.7047 0.4759 0.0170 0.068 Uiso 1 1 calc R . . . .
C13 C 0.5232(3) 0.4504(3) -0.04325(18) 0.0613(7) Uani 1 1 d . . . . .
H13 H 0.5353 0.5091 -0.0880 0.074 Uiso 1 1 calc R . . . .
C14 C 0.4051(4) 0.3839(3) -0.03974(19) 0.0734(9) Uani 1 1 d . . . . .
H14 H 0.3364 0.3974 -0.0818 0.088 Uiso 1 1 calc R . . . .
C15 C 0.3878(3) 0.2960(3) 0.02666(18) 0.0645(7) Uani 1 1 d . . . . .
H15 H 0.3075 0.2503 0.0282 0.077 Uiso 1 1 calc R . . . .
C16 C 0.4430(3) 0.5203(3) 0.57233(19) 0.0630(7) Uani 1 1 d . . . . .
H16 H 0.3984 0.5231 0.5171 0.076 Uiso 1 1 calc R . . . .
C17 C 0.4295(4) 0.6121(3) 0.6393(2) 0.0758(9) Uani 1 1 d . . . . .
H17 H 0.3746 0.6814 0.6333 0.091 Uiso 1 1 calc R . . . .
C18 C 0.5055(4) 0.5871(3) 0.7124(2) 0.0712(8) Uani 1 1 d . . . . .
H18 H 0.5095 0.6378 0.7627 0.085 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 C1 1.723(2) . ?
S1 C18 1.693(4) . ?
O1 C2 1.226(3) . ?
O2 C5 1.351(3) . ?
O2 C6 1.460(3) . ?
O3 C6 1.383(3) . ?
O3 C7 1.453(3) . ?
O4 C5 1.194(3) . ?
C1 C2 1.455(4) . ?
C1 C16 1.358(4) . ?
C2 C3 1.523(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(4) . ?
C4 H4 0.9800 . ?
C4 C5 1.506(4) . ?
C4 C9 1.524(3) . ?
C6 H6 0.9800 . ?
C6 C9 1.518(4) . ?
C7 H7 0.9800 . ?
C7 C8 1.543(3) . ?
C7 C10 1.495(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.523(4) . ?
C9 H9 0.9800 . ?
C10 C11 1.378(3) . ?
C10 C15 1.385(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.390(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.376(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.365(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.386(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C16 C17 1.417(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.345(4) . ?
C18 H18 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
C18 S1 C1 91.52(15) . . ?
C5 O2 C6 109.8(2) . . ?
C6 O3 C7 110.4(2) . . ?
C2 C1 S1 118.83(19) . . ?
C16 C1 S1 110.8(2) . . ?
C16 C1 C2 130.4(2) . . ?
O1 C2 C1 121.5(2) . . ?
O1 C2 C3 121.2(3) . . ?
C1 C2 C3 117.2(2) . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C3 C2 113.2(2) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
C3 C4 H4 107.8 . . ?
C3 C4 C9 117.5(2) . . ?
C5 C4 C3 114.4(2) . . ?
C5 C4 H4 107.8 . . ?
C5 C4 C9 100.88(19) . . ?
C9 C4 H4 107.8 . . ?
O2 C5 C4 110.6(2) . . ?
O4 C5 O2 121.6(2) . . ?
O4 C5 C4 127.9(2) . . ?
O2 C6 H6 111.1 . . ?
O2 C6 C9 104.13(19) . . ?
O3 C6 O2 109.8(2) . . ?
O3 C6 H6 111.1 . . ?
O3 C6 C9 109.3(2) . . ?
C9 C6 H6 111.1 . . ?
O3 C7 H7 108.9 . . ?
O3 C7 C8 104.78(19) . . ?
O3 C7 C10 110.3(2) . . ?
C8 C7 H7 108.9 . . ?
C10 C7 H7 108.9 . . ?
C10 C7 C8 114.8(2) . . ?
C7 C8 H8A 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
C9 C8 C7 104.2(2) . . ?
C9 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C4 C9 H9 112.3 . . ?
C6 C9 C4 102.8(2) . . ?
C6 C9 C8 100.71(19) . . ?
C6 C9 H9 112.3 . . ?
C8 C9 C4 115.5(2) . . ?
C8 C9 H9 112.3 . . ?
C11 C10 C7 121.4(2) . . ?
C11 C10 C15 118.4(2) . . ?
C15 C10 C7 120.2(2) . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 119.9 . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.9 . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.1 . . ?
C10 C15 C14 121.1(3) . . ?
C10 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C1 C16 H16 123.5 . . ?
C1 C16 C17 112.9(3) . . ?
C17 C16 H16 123.5 . . ?
C16 C17 H17 124.1 . . ?
C18 C17 C16 111.9(3) . . ?
C18 C17 H17 124.1 . . ?
S1 C18 H18 123.5 . . ?
C17 C18 S1 112.9(2) . . ?
C17 C18 H18 123.5 . . ?

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
S1 C1 C2 O1 -1.2(3) . . . . ?
S1 C1 C2 C3 177.59(19) . . . . ?
S1 C1 C16 C17 -0.3(3) . . . . ?
O1 C2 C3 C4 -15.9(4) . . . . ?
O2 C6 C9 C4 -31.6(2) . . . . ?
O2 C6 C9 C8 87.8(2) . . . . ?
O3 C6 C9 C4 -148.8(2) . . . . ?
O3 C6 C9 C8 -29.4(3) . . . . ?
O3 C7 C8 C9 -24.4(2) . . . . ?
O3 C7 C10 C11 -47.4(3) . . . . ?
O3 C7 C10 C15 134.0(2) . . . . ?
C1 S1 C18 C17 0.3(3) . . . . ?
C1 C2 C3 C4 165.4(2) . . . . ?
C1 C16 C17 C18 0.6(4) . . . . ?
C2 C1 C16 C17 -179.0(3) . . . . ?
C2 C3 C4 C5 -78.7(3) . . . . ?
C2 C3 C4 C9 163.3(2) . . . . ?
C3 C4 C5 O2 -150.9(2) . . . . ?
C3 C4 C5 O4 28.4(4) . . . . ?
C3 C4 C9 C6 157.8(2) . . . . ?
C3 C4 C9 C8 49.2(3) . . . . ?
C5 O2 C6 O3 134.6(2) . . . . ?
C5 O2 C6 C9 17.8(3) . . . . ?
C5 C4 C9 C6 32.8(2) . . . . ?
C5 C4 C9 C8 -75.9(3) . . . . ?
C6 O2 C5 O4 -175.3(3) . . . . ?
C6 O2 C5 C4 4.0(3) . . . . ?
C6 O3 C7 C8 6.3(3) . . . . ?
C6 O3 C7 C10 130.4(2) . . . . ?
C7 O3 C6 O2 -98.7(3) . . . . ?
C7 O3 C6 C9 14.9(3) . . . . ?
C7 C8 C9 C4 141.5(2) . . . . ?
C7 C8 C9 C6 31.6(2) . . . . ?
C7 C10 C11 C12 -178.6(2) . . . . ?
C7 C10 C15 C14 178.1(3) . . . . ?
C8 C7 C10 C11 70.7(3) . . . . ?
C8 C7 C10 C15 -107.9(3) . . . . ?
C9 C4 C5 O2 -23.7(3) . . . . ?
C9 C4 C5 O4 155.6(3) . . . . ?
C10 C7 C8 C9 -145.7(2) . . . . ?
C10 C11 C12 C13 0.3(4) . . . . ?
C11 C10 C15 C14 -0.5(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 -0.4(5) . . . . ?
C13 C14 C15 C10 0.8(5) . . . . ?
C15 C10 C11 C12 0.0(4) . . . . ?
C16 C1 C2 O1 177.4(3) . . . . ?
C16 C1 C2 C3 -3.8(4) . . . . ?
C16 C17 C18 S1 -0.6(4) . . . . ?
C18 S1 C1 C2 178.9(2) . . . . ?
C18 S1 C1 C16 0.0(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
