# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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. 
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data_cu_19er014_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1986439'
loop_
_audit_author_name
_audit_author_address
'Christelle Kowandy'
;Universite de Reims Champagne Ardenne, Institut de Chimie Moleculaire de Reims 
France
;
_audit_update_record             
;
2020-02-26 deposited with the CCDC.	2020-05-05 downloaded from the CCDC.
;
_audit_creation_date             2019-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        prism
_chemical_formula_moiety         'C20 H26 O4 S'
_chemical_formula_sum            'C20 H26 O4 S'
_chemical_formula_weight         362.47
_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 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.4331(12)
_cell_length_b                   15.335(3)
_cell_length_c                   19.485(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1922.2(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9570
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.504
_cell_measurement_theta_min      3.668
_shelx_estimated_absorpt_T_max   0.644
_shelx_estimated_absorpt_T_min   0.575
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0854 before and 0.0716 after correction. The Ratio of minimum to maximum transmission is 0.9037. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.374
_exptl_crystal_size_mid          0.308
_exptl_crystal_size_min          0.29
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            22927
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.590
_diffrn_reflns_theta_min         3.668
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.725
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3668
_reflns_number_total             3782
_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 V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.206
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.074(6)
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         3782
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0275
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0252P)²+0.4483P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0629
_refine_ls_wR_factor_ref         0.0637
_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, All O(H) groups
2. Restrained distances
 S1B-C13 = S1B-C20B
 1.74 with sigma of 0.001
 S1A-C13 = S1A-C20A
 1.74 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C18A) = Uanis(C17A) = Uanis(C16A)
Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C16A)
Uanis(C15A) = Uanis(C20B) = Uanis(C15B) = Uanis(C20A)
4. Others
 Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)=
 Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=1-FVAR(1)
 Sof(S1B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)=
 Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
5.b Aromatic/amide H refined with riding coordinates:
 C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C14A(H14A),
 C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A)
5.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.84135(19) 0.24729(8) 0.57188(6) 0.0195(3) Uani 1 1 d . . . . .
H1 H 0.792716 0.220555 0.537852 0.029 Uiso 1 1 calc GR . . . .
O2 O 0.1769(2) 0.33904(8) 0.53649(6) 0.0209(3) Uani 1 1 d . . . . .
H2 H 0.069366 0.309329 0.543707 0.031 Uiso 1 1 calc GR . . . .
O3 O 0.5099(2) 0.67600(9) 0.58272(7) 0.0269(3) Uani 1 1 d . . . . .
O4 O 0.1856(2) 0.69298(8) 0.62605(7) 0.0242(3) Uani 1 1 d . . . . .
C1 C 0.0216(5) 0.80186(16) 0.68973(17) 0.0569(8) Uani 1 1 d . . . . .
H1A H -0.085289 0.803715 0.653918 0.085 Uiso 1 1 calc GR . . . .
H1B H 0.031371 0.859067 0.711922 0.085 Uiso 1 1 calc GR . . . .
H1C H -0.015646 0.757737 0.723971 0.085 Uiso 1 1 calc GR . . . .
C2 C 0.2287(4) 0.77884(11) 0.65792(10) 0.0298(5) Uani 1 1 d . . . . .
C3 C 0.3982(5) 0.76910(15) 0.71134(11) 0.0410(6) Uani 1 1 d . . . . .
H3A H 0.357058 0.724807 0.744958 0.062 Uiso 1 1 calc GR . . . .
H3B H 0.419448 0.824988 0.734701 0.062 Uiso 1 1 calc GR . . . .
H3C H 0.527722 0.751197 0.688929 0.062 Uiso 1 1 calc GR . . . .
C4 C 0.2872(4) 0.84428(13) 0.60245(11) 0.0371(5) Uani 1 1 d . . . . .
H4A H 0.426247 0.830725 0.584905 0.056 Uiso 1 1 calc GR . . . .
H4B H 0.286669 0.903237 0.621855 0.056 Uiso 1 1 calc GR . . . .
H4C H 0.186252 0.841011 0.564862 0.056 Uiso 1 1 calc GR . . . .
C5 C 0.3318(3) 0.65273(11) 0.58884(9) 0.0187(4) Uani 1 1 d . . . . .
C6 C 0.2461(3) 0.57419(11) 0.55261(8) 0.0184(3) Uani 1 1 d . . . . .
C7 C 0.0463(3) 0.57196(13) 0.53428(10) 0.0256(4) Uani 1 1 d . . . . .
H7A H -0.054(4) 0.6183(16) 0.5467(12) 0.027(6) Uiso 1 1 d . . . . .
H7B H -0.005(4) 0.5233(16) 0.5043(12) 0.032(6) Uiso 1 1 d . . . . .
C8 C 0.4021(3) 0.50560(12) 0.53272(8) 0.0186(4) Uani 1 1 d . . . . .
H8A H 0.536189 0.534657 0.522847 0.022 Uiso 1 1 calc R . . . .
H8B H 0.354602 0.477479 0.489748 0.022 Uiso 1 1 calc R . . . .
C9 C 0.4401(3) 0.43320(11) 0.58744(8) 0.0147(3) Uani 1 1 d . . . . .
C10 C 0.2408(3) 0.37989(11) 0.59874(8) 0.0162(3) Uani 1 1 d . . . . .
H10A H 0.266026 0.334851 0.634177 0.019 Uiso 1 1 calc R . . . .
H10B H 0.128767 0.418758 0.615433 0.019 Uiso 1 1 calc R . . . .
C11 C 0.6177(3) 0.37511(11) 0.55902(9) 0.0154(3) Uani 1 1 d . . . . .
H11A H 0.574847 0.352689 0.513519 0.018 Uiso 1 1 calc R . . . .
H11B H 0.741828 0.412182 0.551940 0.018 Uiso 1 1 calc R . . . .
C12 C 0.6798(3) 0.29806(11) 0.60351(9) 0.0187(4) Uani 1 1 d . . . . .
H12A H 0.728714 0.319576 0.648599 0.022 Uiso 1 1 calc R . . . .
H12B H 0.556769 0.260590 0.611478 0.022 Uiso 1 1 calc R . . . .
C13 C 0.5025(2) 0.47360(10) 0.65614(7) 0.0136(3) Uani 1 1 d D . . . .
S1B S 0.75358(18) 0.51519(7) 0.66625(5) 0.0158(3) Uani 0.592(3) 1 d D . P A 1
C14B C 0.3924(9) 0.4856(4) 0.7133(3) 0.0254(13) Uani 0.592(3) 1 d . . P A 1
H14B H 0.251401 0.467766 0.716813 0.031 Uiso 0.592(3) 1 calc R . P A 1
C15B C 0.4969(10) 0.5264(9) 0.7681(4) 0.0164(4) Uani 0.592(3) 1 d . . P A 1
C16B C 0.4260(8) 0.5477(3) 0.8343(2) 0.0182(4) Uani 0.592(3) 1 d . . P A 1
H16B H 0.287845 0.534128 0.847797 0.022 Uiso 0.592(3) 1 calc R . P A 1
C17B C 0.5600(6) 0.5886(2) 0.87925(19) 0.0182(4) Uani 0.592(3) 1 d . . P A 1
H17B H 0.513564 0.602307 0.924266 0.022 Uiso 0.592(3) 1 calc R . P A 1
C18B C 0.7622(7) 0.6103(2) 0.85988(18) 0.0182(4) Uani 0.592(3) 1 d . . P A 1
H18B H 0.850251 0.639087 0.891807 0.022 Uiso 0.592(3) 1 calc R . P A 1
C19B C 0.8371(10) 0.5908(3) 0.7954(2) 0.0206(12) Uani 0.592(3) 1 d . . P A 1
H19B H 0.975140 0.605248 0.782301 0.025 Uiso 0.592(3) 1 calc R . P A 1
C20B C 0.7003(12) 0.5486(8) 0.7498(3) 0.0164(4) Uani 0.592(3) 1 d D . P A 1
S1A S 0.3157(3) 0.48175(15) 0.72077(9) 0.0172(5) Uani 0.408(3) 1 d D . P A 2
C14A C 0.6736(15) 0.5057(6) 0.6758(4) 0.033(2) Uani 0.408(3) 1 d . . P A 2
H14A H 0.790243 0.506225 0.645963 0.039 Uiso 0.408(3) 1 calc R . P A 2
C15A C 0.6895(18) 0.5408(12) 0.7425(4) 0.0164(4) Uani 0.408(3) 1 d . . P A 2
C16A C 0.8480(18) 0.5817(6) 0.7792(5) 0.0182(4) Uani 0.408(3) 1 d . . P A 2
H16A H 0.980117 0.589496 0.758276 0.022 Uiso 0.408(3) 1 calc R . P A 2
C17A C 0.8168(9) 0.6109(4) 0.8446(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2
H17A H 0.926569 0.639266 0.868396 0.022 Uiso 0.408(3) 1 calc R . P A 2
C18A C 0.6266(9) 0.5994(4) 0.8765(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2
H18A H 0.609601 0.618584 0.922537 0.022 Uiso 0.408(3) 1 calc R . P A 2
C19A C 0.4602(12) 0.5607(4) 0.8432(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2
H19A H 0.329845 0.553301 0.865355 0.022 Uiso 0.408(3) 1 calc R . P A 2
C20A C 0.4920(14) 0.5327(13) 0.7753(6) 0.0164(4) Uani 0.408(3) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C12 1.438(2) . ?
O2 C10 1.426(2) . ?
O3 C5 1.206(2) . ?
O4 C2 1.482(2) . ?
O4 C5 1.338(2) . ?
C1 C2 1.512(3) . ?
C2 C3 1.515(3) . ?
C2 C4 1.522(3) . ?
C5 C6 1.501(2) . ?
C6 C7 1.335(3) . ?
C6 C8 1.504(2) . ?
C8 C9 1.559(2) . ?
C9 C10 1.536(2) . ?
C9 C11 1.551(2) . ?
C9 C13 1.529(2) . ?
C11 C12 1.519(2) . ?
C13 S1B 1.7474(12) . ?
C13 C14B 1.332(7) . ?
C13 S1A 1.7455(12) . ?
C13 C14A 1.265(10) . ?
S1B C20B 1.7403(14) . ?
C14B C15B 1.408(6) . ?
C15B C16B 1.407(8) . ?
C15B C20B 1.399(10) . ?
C16B C17B 1.381(4) . ?
C17B C18B 1.395(5) . ?
C18B C19B 1.378(5) . ?
C19B C20B 1.409(7) . ?
S1A C20A 1.7400(14) . ?
C14A C15A 1.410(9) . ?
C15A C16A 1.395(14) . ?
C15A C20A 1.427(14) . ?
C16A C17A 1.365(8) . ?
C17A C18A 1.384(7) . ?
C18A C19A 1.385(6) . ?
C19A C20A 1.406(11) . ?

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
C5 O4 C2 120.36(15) . . ?
O4 C2 C1 102.38(17) . . ?
O4 C2 C3 109.57(16) . . ?
O4 C2 C4 109.54(15) . . ?
C1 C2 C3 112.1(2) . . ?
C1 C2 C4 110.8(2) . . ?
C3 C2 C4 112.0(2) . . ?
O3 C5 O4 125.78(17) . . ?
O3 C5 C6 122.67(17) . . ?
O4 C5 C6 111.53(15) . . ?
C5 C6 C8 115.92(16) . . ?
C7 C6 C5 120.01(17) . . ?
C7 C6 C8 123.75(17) . . ?
C6 C8 C9 115.24(14) . . ?
C10 C9 C8 110.25(14) . . ?
C10 C9 C11 111.12(13) . . ?
C11 C9 C8 106.28(13) . . ?
C13 C9 C8 110.59(13) . . ?
C13 C9 C10 108.03(12) . . ?
C13 C9 C11 110.60(13) . . ?
O2 C10 C9 110.64(13) . . ?
C12 C11 C9 115.89(14) . . ?
O1 C12 C11 111.51(14) . . ?
C9 C13 S1B 119.31(10) . . ?
C9 C13 S1A 118.67(12) . . ?
C14B C13 C9 130.4(2) . . ?
C14B C13 S1B 110.3(3) . . ?
C14A C13 C9 130.7(3) . . ?
C14A C13 S1A 110.6(3) . . ?
C20B S1B C13 91.8(2) . . ?
C13 C14B C15B 116.2(5) . . ?
C16B C15B C14B 130.1(6) . . ?
C20B C15B C14B 111.2(5) . . ?
C20B C15B C16B 118.7(3) . . ?
C17B C16B C15B 119.0(4) . . ?
C16B C17B C18B 121.3(3) . . ?
C19B C18B C17B 121.4(4) . . ?
C18B C19B C20B 117.2(5) . . ?
C15B C20B S1B 110.5(4) . . ?
C15B C20B C19B 122.4(3) . . ?
C19B C20B S1B 127.1(4) . . ?
C20A S1A C13 91.4(3) . . ?
C13 C14A C15A 119.4(7) . . ?
C14A C15A C20A 108.3(7) . . ?
C16A C15A C14A 134.2(9) . . ?
C16A C15A C20A 117.4(6) . . ?
C17A C16A C15A 121.2(10) . . ?
C16A C17A C18A 120.5(7) . . ?
C17A C18A C19A 121.8(5) . . ?
C18A C19A C20A 117.3(7) . . ?
C15A C20A S1A 110.2(6) . . ?
C19A C20A S1A 128.1(7) . . ?
C19A C20A C15A 121.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
