# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_er1
_database_code_depnum_ccdc_archive 'CCDC 2123381'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C34 H12 F10 O4 S2'
_chemical_formula_weight         738.56

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.9881(11)
_cell_length_b                   7.0240(11)
_cell_length_c                   15.623(3)
_cell_angle_alpha                89.898(6)
_cell_angle_beta                 82.720(6)
_cell_angle_gamma                72.540(6)
_cell_volume                     725.1(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9796
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.41

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_F_000             370
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.291
_shelx_estimated_absorpt_T_min   0.943
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595286
_exptl_absorpt_correction_T_max  0.746027
_exptl_absorpt_process_details   'TWINABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            4346
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_av_R_equivalents  0.0622
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.315
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             4346
_reflns_number_gt                3738
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 _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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component non-merohedral twin. 

 Twofold disorder
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+0.9447P] 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_number_reflns         4346
_refine_ls_number_parameters     264
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1297
_refine_ls_wR_factor_gt          0.1194
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.057
_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
F1 F 0.2413(3) 0.9491(3) 0.27315(14) 0.0441(5) Uani 1 1 d . . . . .
F2 F 0.3642(3) 0.9023(3) 0.10008(14) 0.0523(5) Uani 1 1 d . . . . .
F3 F 0.7639(4) 0.7737(3) 0.03953(12) 0.0507(5) Uani 1 1 d . . . . .
F4 F 1.0425(3) 0.6955(3) 0.15153(14) 0.0508(5) Uani 1 1 d . . . . .
F5 F 0.9228(3) 0.7413(3) 0.32305(13) 0.0427(5) Uani 1 1 d . . . . .
O1 O 0.2321(4) 0.8900(4) 0.53716(15) 0.0484(7) Uani 1 1 d . . . . .
O2 O 0.4000(3) 0.7167(3) 0.41683(13) 0.0360(5) Uani 1 1 d . . . . .
C1 C 0.1341(4) 0.6152(4) 0.49002(16) 0.0213(4) Uani 1 1 d . . . . .
C2 C -0.0222(4) 0.6539(4) 0.55889(15) 0.0214(4) Uani 1 1 d . . . . .
H2 H -0.037035 0.760177 0.599150 0.026 Uiso 1 1 calc R U . . .
C3 C -0.1579(4) 0.5415(4) 0.57066(16) 0.0219(4) Uani 1 1 d . . . . .
C4 C -0.3097(4) 0.5914(4) 0.64543(16) 0.0233(5) Uani 1 1 d . . . . .
C5 C -0.4297(4) 0.6329(4) 0.70985(17) 0.0251(5) Uani 1 1 d D U . . .
C6 C -0.5802(4) 0.6725(4) 0.78345(17) 0.0259(5) Uani 1 1 d D U . . .
C7 C -0.7885(15) 0.730(2) 0.7872(6) 0.0320(19) Uani 0.601(4) 1 d D U P A 1
H7 H -0.853214 0.750761 0.736605 0.038 Uiso 0.601(4) 1 calc R U P A 1
C8 C -0.896(2) 0.754(3) 0.8682(7) 0.0326(17) Uani 0.601(4) 1 d D U P A 1
H8 H -1.039759 0.789795 0.879411 0.039 Uiso 0.601(4) 1 calc R U P A 1
C9 C -0.7723(14) 0.722(3) 0.9299(9) 0.0314(18) Uani 0.601(4) 1 d D U P A 1
H9 H -0.819017 0.735645 0.990075 0.038 Uiso 0.601(4) 1 calc R U P A 1
S1 S -0.5160(3) 0.6522(5) 0.88703(12) 0.0304(5) Uani 0.601(4) 1 d D U P A 1
C7A C -0.559(2) 0.666(3) 0.8698(8) 0.037(3) Uani 0.399(4) 1 d D U P A 2
H7A H -0.429588 0.636823 0.888956 0.044 Uiso 0.399(4) 1 calc R U P A 2
C8A C -0.733(2) 0.704(4) 0.9265(15) 0.037(3) Uani 0.399(4) 1 d D U P A 2
H8A H -0.738676 0.697445 0.987471 0.044 Uiso 0.399(4) 1 calc R U P A 2
C9A C -0.895(4) 0.752(5) 0.8826(10) 0.038(3) Uani 0.399(4) 1 d D U P A 2
H9A H -1.030600 0.790283 0.910239 0.046 Uiso 0.399(4) 1 calc R U P A 2
S1A S -0.8300(5) 0.7361(7) 0.7696(2) 0.0326(8) Uani 0.399(4) 1 d D U P A 2
C10 C 0.2590(4) 0.7553(4) 0.48515(16) 0.0234(5) Uani 1 1 d . . . . .
C11 C 0.5088(5) 0.8622(4) 0.39838(18) 0.0308(6) Uani 1 1 d . . . . .
H11A H 0.626230 0.834372 0.430977 0.037 Uiso 1 1 calc R U . . .
H11B H 0.418906 0.998941 0.414636 0.037 Uiso 1 1 calc R U . . .
C12 C 0.5779(4) 0.8421(4) 0.30320(17) 0.0253(5) Uani 1 1 d . . . . .
C13 C 0.4404(4) 0.8833(4) 0.24413(19) 0.0303(6) Uani 1 1 d . . . . .
C14 C 0.5005(5) 0.8609(4) 0.15586(19) 0.0344(6) Uani 1 1 d . . . . .
C15 C 0.7051(5) 0.7961(5) 0.12526(18) 0.0348(6) Uani 1 1 d . . . . .
C16 C 0.8445(4) 0.7575(4) 0.18159(19) 0.0315(6) Uani 1 1 d . . . . .
C17 C 0.7805(4) 0.7803(4) 0.26957(18) 0.0273(5) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C13 1.346(3) . ?
F2 C14 1.340(4) . ?
F3 C15 1.345(3) . ?
F4 C16 1.341(3) . ?
F5 C17 1.345(3) . ?
O1 C10 1.203(3) . ?
O2 C10 1.326(3) . ?
O2 C11 1.454(3) . ?
C1 C2 1.396(3) . ?
C1 C3 1.411(3) 2_566 ?
C1 C10 1.495(3) . ?
C2 C3 1.401(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.441(3) . ?
C4 C5 1.201(3) . ?
C5 C6 1.423(3) . ?
C6 C7A 1.375(12) . ?
C6 C7 1.383(10) . ?
C6 S1A 1.709(4) . ?
C6 S1 1.728(3) . ?
C7 C8 1.370(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.352(9) . ?
C8 H8 0.9500 . ?
C9 S1 1.751(10) . ?
C9 H9 0.9500 . ?
C7A C8A 1.37(2) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.355(14) . ?
C8A H8A 0.9500 . ?
C9A S1A 1.763(16) . ?
C9A H9A 0.9500 . ?
C11 C12 1.497(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.383(3) . ?
C12 C13 1.384(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.385(5) . ?
C15 C16 1.362(5) . ?
C16 C17 1.385(4) . ?

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
C10 O2 C11 117.1(2) . . ?
C2 C1 C3 119.7(2) . 2_566 ?
C2 C1 C10 115.2(2) . . ?
C3 C1 C10 125.1(2) 2_566 . ?
C1 C2 C3 122.3(2) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C1 118.0(2) . 2_566 ?
C2 C3 C4 117.4(2) . . ?
C1 C3 C4 124.5(2) 2_566 . ?
C5 C4 C3 177.2(3) . . ?
C4 C5 C6 175.5(3) . . ?
C7A C6 C5 129.7(6) . . ?
C7 C6 C5 129.2(5) . . ?
C7A C6 S1A 110.8(6) . . ?
C5 C6 S1A 119.5(2) . . ?
C7 C6 S1 109.4(4) . . ?
C5 C6 S1 121.5(2) . . ?
C8 C7 C6 116.2(9) . . ?
C8 C7 H7 121.9 . . ?
C6 C7 H7 121.9 . . ?
C9 C8 C7 111.2(14) . . ?
C9 C8 H8 124.4 . . ?
C7 C8 H8 124.4 . . ?
C8 C9 S1 112.7(13) . . ?
C8 C9 H9 123.7 . . ?
S1 C9 H9 123.7 . . ?
C6 S1 C9 90.5(5) . . ?
C8A C7A C6 116.5(14) . . ?
C8A C7A H7A 121.7 . . ?
C6 C7A H7A 121.7 . . ?
C9A C8A C7A 110(2) . . ?
C9A C8A H8A 125.1 . . ?
C7A C8A H8A 125.1 . . ?
C8A C9A S1A 113.6(19) . . ?
C8A C9A H9A 123.2 . . ?
S1A C9A H9A 123.2 . . ?
C6 S1A C9A 89.3(8) . . ?
O1 C10 O2 123.9(2) . . ?
O1 C10 C1 123.4(2) . . ?
O2 C10 C1 112.7(2) . . ?
O2 C11 C12 106.1(2) . . ?
O2 C11 H11A 110.5 . . ?
C12 C11 H11A 110.5 . . ?
O2 C11 H11B 110.5 . . ?
C12 C11 H11B 110.5 . . ?
H11A C11 H11B 108.7 . . ?
C17 C12 C13 116.5(2) . . ?
C17 C12 C11 122.3(2) . . ?
C13 C12 C11 121.2(2) . . ?
F1 C13 C12 119.1(2) . . ?
F1 C13 C14 118.6(3) . . ?
C12 C13 C14 122.3(3) . . ?
F2 C14 C15 119.8(3) . . ?
F2 C14 C13 121.1(3) . . ?
C15 C14 C13 119.1(3) . . ?
F3 C15 C16 120.7(3) . . ?
F3 C15 C14 119.2(3) . . ?
C16 C15 C14 120.1(3) . . ?
F4 C16 C15 119.8(3) . . ?
F4 C16 C17 120.5(3) . . ?
C15 C16 C17 119.6(3) . . ?
F5 C17 C12 119.8(2) . . ?
F5 C17 C16 117.8(2) . . ?
C12 C17 C16 122.3(3) . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.065


####################################################################### 
# 
# 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_wm72
_database_code_depnum_ccdc_archive 'CCDC 2163192'
loop_
_audit_author_name
_audit_author_address
'Peter Muller'
;MIT
United States of America
;
_audit_update_record             
;
2022-03-30 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C42 H16 F10 O4 S2'
_chemical_formula_weight         838.67

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'
F F 0.0171 0.0103 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   7.1753(8)
_cell_length_b                   7.4190(8)
_cell_length_c                   16.0501(19)
_cell_angle_alpha                89.010(4)
_cell_angle_beta                 79.454(4)
_cell_angle_gamma                84.755(4)
_cell_volume                     836.45(16)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9530
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      32.60

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_F_000             422
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.305
_exptl_crystal_size_min          0.175
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7170
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            81800
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.290
_diffrn_reflns_theta_max         32.577
_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             6093
_reflns_number_gt                5743
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Kappa DUO four-circle diffractometer, Bruker Photon3 CPAD. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0460P)²+0.2915P] 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_number_reflns         6093
_refine_ls_number_parameters     287
_refine_ls_number_restraints     436
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_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
F1 F 0.13837(10) 1.40321(8) 0.66526(4) 0.02386(13) Uani 1 1 d . . . . .
F2 F -0.06062(10) 1.48316(9) 0.82139(4) 0.02656(14) Uani 1 1 d . . . . .
F3 F -0.13158(9) 1.21457(10) 0.93770(4) 0.02695(14) Uani 1 1 d . . . . .
F4 F -0.00258(10) 0.86633(10) 0.89589(4) 0.02777(14) Uani 1 1 d . . . . .
F5 F 0.18927(9) 0.78471(8) 0.73785(4) 0.02138(12) Uani 1 1 d . . . . .
O1 O 0.41217(11) 0.74491(11) 0.51546(6) 0.03032(19) Uani 1 1 d . . . . .
O2 O 0.15125(9) 0.92176(9) 0.57375(4) 0.01577(12) Uani 1 1 d . . . . .
C1 C 0.10806(11) 0.63903(11) 0.51751(5) 0.01233(13) Uani 1 1 d . . . . .
C2 C 0.18941(11) 0.49867(11) 0.46250(5) 0.01327(14) Uani 1 1 d . . . . .
H2 H 0.320007 0.497414 0.437173 0.016 Uiso 1 1 calc R U . . .
C3 C 0.08517(11) 0.35903(11) 0.44318(5) 0.01268(13) Uani 1 1 d . . . . .
C4 C 0.18023(12) 0.22852(12) 0.38165(6) 0.01562(15) Uani 1 1 d . . . . .
C5 C 0.26666(12) 0.12689(13) 0.32714(6) 0.01848(16) Uani 1 1 d D U . . .
C6 C 0.36069(12) 0.00089(12) 0.26471(5) 0.01438(14) Uani 1 1 d D U . . .
C7 C 0.3916(3) -0.1877(3) 0.27206(14) 0.01417(17) Uani 0.5982(16) 1 d D U P A 1
H7 H 0.347741 -0.253350 0.322077 0.017 Uiso 0.5982(16) 1 calc R U P A 1
C8 C 0.497(3) -0.2704(16) 0.1954(10) 0.0130(9) Uani 0.5982(16) 1 d D U P A 1
C9 C 0.560(2) -0.4525(15) 0.1774(7) 0.0173(8) Uani 0.5982(16) 1 d D U P A 1
H9 H 0.538013 -0.541684 0.220398 0.021 Uiso 0.5982(16) 1 calc R U P A 1
C10 C 0.654(2) -0.5014(16) 0.0974(7) 0.0207(7) Uani 0.5982(16) 1 d D U P A 1
H10 H 0.688939 -0.625901 0.084793 0.025 Uiso 0.5982(16) 1 calc R U P A 1
C11 C 0.7010(17) -0.3713(8) 0.0337(7) 0.0186(7) Uani 0.5982(16) 1 d D U P A 1
H11 H 0.773410 -0.407438 -0.019947 0.022 Uiso 0.5982(16) 1 calc R U P A 1
C12 C 0.640(2) -0.1877(14) 0.0502(8) 0.0168(7) Uani 0.5982(16) 1 d D U P A 1
H12 H 0.669412 -0.098095 0.008038 0.020 Uiso 0.5982(16) 1 calc R U P A 1
C13 C 0.533(3) -0.140(2) 0.1307(7) 0.0127(8) Uani 0.5982(16) 1 d D U P A 1
S1 S 0.45005(6) 0.07733(6) 0.16577(3) 0.01369(11) Uani 0.5982(16) 1 d D U P A 1
C7A C 0.4497(4) 0.0314(4) 0.1797(2) 0.01369(11) Uani 0.4018(16) 1 d D U P A 2
H7A H 0.453588 0.146708 0.153086 0.016 Uiso 0.4018(16) 1 calc R U P A 2
C8A C 0.534(5) -0.137(3) 0.1390(11) 0.0127(8) Uani 0.4018(16) 1 d D U P A 2
C9A C 0.631(4) -0.170(2) 0.0564(12) 0.0168(7) Uani 0.4018(16) 1 d D U P A 2
H9A H 0.653531 -0.072518 0.017531 0.020 Uiso 0.4018(16) 1 calc R U P A 2
C10A C 0.692(3) -0.3417(14) 0.0325(10) 0.0186(7) Uani 0.4018(16) 1 d D U P A 2
H10A H 0.755980 -0.363542 -0.024132 0.022 Uiso 0.4018(16) 1 calc R U P A 2
C11A C 0.664(4) -0.490(2) 0.0877(11) 0.0207(7) Uani 0.4018(16) 1 d D U P A 2
H11A H 0.719526 -0.607443 0.069994 0.025 Uiso 0.4018(16) 1 calc R U P A 2
C12A C 0.555(3) -0.464(2) 0.1689(10) 0.0173(8) Uani 0.4018(16) 1 d D U P A 2
H12A H 0.524624 -0.562665 0.205621 0.021 Uiso 0.4018(16) 1 calc R U P A 2
C13A C 0.491(5) -0.285(2) 0.1938(16) 0.0130(9) Uani 0.4018(16) 1 d D U P A 2
S1A S 0.37493(10) -0.21728(10) 0.29388(5) 0.01417(17) Uani 0.4018(16) 1 d D U P
A 2
C14 C 0.24133(12) 0.77249(11) 0.53467(5) 0.01478(14) Uani 1 1 d . . . . .
C15 C 0.26867(12) 1.04079(12) 0.60808(5) 0.01592(15) Uani 1 1 d . . . . .
H15A H 0.285604 1.150502 0.572503 0.019 Uiso 1 1 calc R U . . .
H15B H 0.395627 0.977919 0.609946 0.019 Uiso 1 1 calc R U . . .
C16 C 0.16609(11) 1.09092(11) 0.69606(5) 0.01244(13) Uani 1 1 d . . . . .
C17 C 0.10282(13) 1.26770(11) 0.72045(5) 0.01475(14) Uani 1 1 d . . . . .
C18 C 0.00226(13) 1.31151(12) 0.80100(6) 0.01685(15) Uani 1 1 d . . . . .
C19 C -0.03452(12) 1.17549(13) 0.85982(5) 0.01753(16) Uani 1 1 d . . . . .
C20 C 0.02943(13) 0.99752(13) 0.83829(5) 0.01715(15) Uani 1 1 d . . . . .
C21 C 0.12812(12) 0.95775(11) 0.75733(5) 0.01429(14) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C17 1.3394(10) . ?
F2 C18 1.3371(10) . ?
F3 C19 1.3374(10) . ?
F4 C20 1.3368(11) . ?
F5 C21 1.3413(10) . ?
O1 C14 1.2073(11) . ?
O2 C14 1.3350(10) . ?
O2 C15 1.4546(10) . ?
C1 C2 1.3916(11) . ?
C1 C3 1.4132(11) 2_566 ?
C1 C14 1.4998(12) . ?
C2 C3 1.4024(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.4296(11) . ?
C4 C5 1.2071(12) . ?
C5 C6 1.4151(12) . ?
C6 C7 1.403(2) . ?
C6 C7A 1.421(3) . ?
C6 S1A 1.6764(12) . ?
C6 S1 1.7080(10) . ?
C7 C8 1.436(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.403(13) . ?
C8 C13 1.412(7) . ?
C9 C10 1.375(10) . ?
C9 H9 0.9500 . ?
C10 C11 1.410(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.407(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.410(12) . ?
C12 H12 0.9500 . ?
C13 S1 1.733(13) . ?
C7A C8A 1.445(19) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.396(18) . ?
C8A C13A 1.414(11) . ?
C9A C10A 1.349(15) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.406(10) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.400(16) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.404(19) . ?
C12A H12A 0.9500 . ?
C13A S1A 1.73(2) . ?
C15 C16 1.5039(12) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.3869(11) . ?
C16 C21 1.3910(12) . ?
C17 C18 1.3884(12) . ?
C18 C19 1.3797(14) . ?
C19 C20 1.3858(13) . ?
C20 C21 1.3839(12) . ?

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
C14 O2 C15 116.41(7) . . ?
C2 C1 C3 119.51(7) . 2_566 ?
C2 C1 C14 115.52(7) . . ?
C3 C1 C14 124.83(7) 2_566 . ?
C1 C2 C3 122.24(7) . . ?
C1 C2 H2 118.9 . . ?
C3 C2 H2 118.9 . . ?
C2 C3 C1 118.24(7) . 2_566 ?
C2 C3 C4 117.32(7) . . ?
C1 C3 C4 124.37(8) 2_566 . ?
C5 C4 C3 175.91(10) . . ?
C4 C5 C6 176.90(10) . . ?
C7 C6 C5 128.30(12) . . ?
C5 C6 C7A 129.51(15) . . ?
C5 C6 S1A 116.64(7) . . ?
C7A C6 S1A 113.84(13) . . ?
C7 C6 S1 112.58(10) . . ?
C5 C6 S1 119.11(7) . . ?
C6 C7 C8 112.3(6) . . ?
C6 C7 H7 123.8 . . ?
C8 C7 H7 123.8 . . ?
C9 C8 C13 119.1(14) . . ?
C9 C8 C7 130.1(11) . . ?
C13 C8 C7 110.8(10) . . ?
C10 C9 C8 119.8(12) . . ?
C10 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?
C9 C10 C11 121.7(11) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 H10 119.2 . . ?
C12 C11 C10 119.6(10) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C11 C12 C13 118.4(11) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C12 C13 C8 121.3(14) . . ?
C12 C13 S1 126.2(10) . . ?
C8 C13 S1 112.3(10) . . ?
C6 S1 C13 91.9(4) . . ?
C6 C7A C8A 110.9(8) . . ?
C6 C7A H7A 124.5 . . ?
C8A C7A H7A 124.5 . . ?
C9A C8A C13A 119(2) . . ?
C9A C8A C7A 130.1(17) . . ?
C13A C8A C7A 110.4(16) . . ?
C10A C9A C8A 118.9(17) . . ?
C10A C9A H9A 120.6 . . ?
C8A C9A H9A 120.6 . . ?
C9A C10A C11A 122.9(16) . . ?
C9A C10A H10A 118.6 . . ?
C11A C10A H10A 118.6 . . ?
C12A C11A C10A 119.7(18) . . ?
C12A C11A H11A 120.2 . . ?
C10A C11A H11A 120.2 . . ?
C11A C12A C13A 117.3(17) . . ?
C11A C12A H12A 121.4 . . ?
C13A C12A H12A 121.4 . . ?
C12A C13A C8A 122(2) . . ?
C12A C13A S1A 125.5(16) . . ?
C8A C13A S1A 112.6(15) . . ?
C6 S1A C13A 91.9(6) . . ?
O1 C14 O2 124.25(8) . . ?
O1 C14 C1 122.74(8) . . ?
O2 C14 C1 113.01(7) . . ?
O2 C15 C16 106.58(7) . . ?
O2 C15 H15A 110.4 . . ?
C16 C15 H15A 110.4 . . ?
O2 C15 H15B 110.4 . . ?
C16 C15 H15B 110.4 . . ?
H15A C15 H15B 108.6 . . ?
C17 C16 C21 116.62(8) . . ?
C17 C16 C15 122.99(8) . . ?
C21 C16 C15 120.39(7) . . ?
F1 C17 C16 119.81(8) . . ?
F1 C17 C18 117.77(8) . . ?
C16 C17 C18 122.42(8) . . ?
F2 C18 C19 120.09(8) . . ?
F2 C18 C17 120.61(8) . . ?
C19 C18 C17 119.29(8) . . ?
F3 C19 C18 120.30(9) . . ?
F3 C19 C20 119.74(9) . . ?
C18 C19 C20 119.97(8) . . ?
F4 C20 C21 120.61(9) . . ?
F4 C20 C19 119.92(8) . . ?
C21 C20 C19 119.46(8) . . ?
F5 C21 C20 118.52(8) . . ?
F5 C21 C16 119.26(8) . . ?
C20 C21 C16 122.22(8) . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.071



####################################################################### 
# 
# 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_er1h
_database_code_depnum_ccdc_archive 'CCDC 2123382'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C34 H22 O4 S2'
_chemical_formula_weight         558.63

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.1412(11)
_cell_length_b                   4.8090(3)
_cell_length_c                   18.5187(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.317(3)
_cell_angle_gamma                90
_cell_volume                     1300.52(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9966
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      27.14

_exptl_crystal_description       Prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             580
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.246
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6904
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube, Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            49570
_diffrn_reflns_av_unetI/netI     0.0138
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.281
_diffrn_reflns_theta_max         27.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2880
_reflns_number_gt                2512
_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
 'Bruker D8 three-circle diffractometer, Bruker Photon 100 CMOS detector' 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²+0.7693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         2880
_refine_ls_number_parameters     194
_refine_ls_number_restraints     209
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0883
_refine_ls_wR_factor_gt          0.0838
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      0.995
_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
O1 O 0.32288(6) 1.1745(2) 0.32942(5) 0.0261(2) Uani 1 1 d . . . . .
O2 O 0.44683(6) 1.42829(19) 0.32887(5) 0.0162(2) Uani 1 1 d . . . . .
C1 C 0.45621(8) 1.1239(2) 0.43095(6) 0.0115(2) Uani 1 1 d . . . . .
C2 C 0.41378(8) 0.9150(2) 0.46125(6) 0.0120(2) Uani 1 1 d . . . . .
H2 H 0.354197 0.856843 0.434399 0.014 Uiso 1 1 calc R U . . .
C3 C 0.45505(8) 0.7864(2) 0.52974(6) 0.0113(2) Uani 1 1 d . . . . .
C4 C 0.40504(8) 0.5730(2) 0.55532(6) 0.0126(2) Uani 1 1 d . . . . .
C5 C 0.36011(8) 0.3953(3) 0.57404(7) 0.0148(2) Uani 1 1 d D U . . .
C6 C 0.31631(8) 0.1839(3) 0.60499(7) 0.0162(3) Uani 1 1 d D U . . .
C7 C 0.2337(4) 0.0517(16) 0.5748(4) 0.0224(5) Uani 0.655(2) 1 d D U P A 1
H7 H 0.194805 0.092791 0.526672 0.027 Uiso 0.655(2) 1 calc R U P A 1
C8 C 0.2132(11) -0.155(3) 0.6241(6) 0.0253(8) Uani 0.655(2) 1 d D U P A 1
H8 H 0.159793 -0.267483 0.613121 0.030 Uiso 0.655(2) 1 calc R U P A 1
C9 C 0.2811(9) -0.166(3) 0.6886(9) 0.0229(8) Uani 0.655(2) 1 d D U P A 1
H9 H 0.279691 -0.286455 0.728865 0.027 Uiso 0.655(2) 1 calc R U P A 1
S1 S 0.36935(5) 0.0577(2) 0.69095(4) 0.0179(2) Uani 0.655(2) 1 d D U P A 1
C7A C 0.3484(5) 0.0571(18) 0.6769(4) 0.0179(2) Uani 0.345(2) 1 d D U P A 2
H7A H 0.404011 0.110011 0.711711 0.021 Uiso 0.345(2) 1 calc R U P A 2
C8A C 0.2898(17) -0.157(6) 0.6922(17) 0.0229(8) Uani 0.345(2) 1 d D U P A 2
H8A H 0.301289 -0.271025 0.735479 0.027 Uiso 0.345(2) 1 calc R U P A 2
C9A C 0.215(2) -0.164(6) 0.6333(12) 0.0253(8) Uani 0.345(2) 1 d D U P A 2
H9A H 0.164921 -0.282254 0.632717 0.030 Uiso 0.345(2) 1 calc R U P A 2
S1A S 0.21566(14) 0.0466(7) 0.56041(15) 0.0224(5) Uani 0.345(2) 1 d D U P A 2
C10 C 0.40101(8) 1.2423(3) 0.35807(7) 0.0138(2) Uani 1 1 d . . . . .
C11 C 0.39833(9) 1.5511(3) 0.25682(7) 0.0165(3) Uani 1 1 d . . . . .
H11A H 0.423348 1.738527 0.252187 0.020 Uiso 1 1 calc R U . . .
H11B H 0.332580 1.571335 0.254548 0.020 Uiso 1 1 calc R U . . .
C12 C 0.40859(8) 1.3713(3) 0.19312(7) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.48903(9) 1.3799(3) 0.17003(7) 0.0213(3) Uani 1 1 d . . . . .
H13 H 0.537199 1.501544 0.194239 0.026 Uiso 1 1 calc R U . . .
C14 C 0.49910(10) 1.2115(3) 0.11183(8) 0.0261(3) Uani 1 1 d . . . . .
H14 H 0.554185 1.217988 0.096484 0.031 Uiso 1 1 calc R U . . .
C15 C 0.42917(10) 1.0342(3) 0.07608(8) 0.0256(3) Uani 1 1 d . . . . .
H15 H 0.436249 0.919293 0.036264 0.031 Uiso 1 1 calc R U . . .
C16 C 0.34876(10) 1.0246(3) 0.09846(8) 0.0239(3) Uani 1 1 d . . . . .
H16 H 0.300620 0.903311 0.073966 0.029 Uiso 1 1 calc R U . . .
C17 C 0.33881(9) 1.1927(3) 0.15679(7) 0.0187(3) Uani 1 1 d . . . . .
H17 H 0.283661 1.185550 0.172018 0.022 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
O1 C10 1.2065(15) . ?
O2 C10 1.3311(15) . ?
O2 C11 1.4666(14) . ?
C1 C2 1.3883(16) . ?
C1 C3 1.4158(16) 3_676 ?
C1 C10 1.4995(16) . ?
C2 C3 1.4012(16) . ?
C2 H2 0.9500 . ?
C3 C4 1.4281(16) . ?
C4 C5 1.1994(18) . ?
C5 C6 1.4149(17) . ?
C6 C7 1.382(6) . ?
C6 C7A 1.428(7) . ?
C6 S1A 1.666(2) . ?
C6 S1 1.6948(14) . ?
C7 C8 1.438(13) . ?
C7 H7 0.9500 . ?
C8 C9 1.355(7) . ?
C8 H8 0.9500 . ?
C9 S1 1.705(10) . ?
C9 H9 0.9500 . ?
C7A C8A 1.43(2) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.346(13) . ?
C8A H8A 0.9500 . ?
C9A S1A 1.688(19) . ?
C9A H9A 0.9500 . ?
C11 C12 1.5033(17) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C17 1.3897(18) . ?
C12 C13 1.3939(18) . ?
C13 C14 1.3883(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.386(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3890(19) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 116.80(9) . . ?
C2 C1 C3 119.37(11) . 3_676 ?
C2 C1 C10 115.53(10) . . ?
C3 C1 C10 125.08(11) 3_676 . ?
C1 C2 C3 122.83(11) . . ?
C1 C2 H2 118.6 . . ?
C3 C2 H2 118.6 . . ?
C2 C3 C1 117.81(11) . 3_676 ?
C2 C3 C4 117.95(10) . . ?
C1 C3 C4 124.25(11) 3_676 . ?
C5 C4 C3 177.21(13) . . ?
C4 C5 C6 172.50(14) . . ?
C7 C6 C5 129.6(3) . . ?
C5 C6 C7A 127.1(3) . . ?
C5 C6 S1A 123.32(14) . . ?
C7A C6 S1A 109.5(3) . . ?
C7 C6 S1 111.7(3) . . ?
C5 C6 S1 118.77(10) . . ?
C6 C7 C8 112.6(7) . . ?
C6 C7 H7 123.7 . . ?
C8 C7 H7 123.7 . . ?
C9 C8 C7 110.2(13) . . ?
C9 C8 H8 124.9 . . ?
C7 C8 H8 124.9 . . ?
C8 C9 S1 113.9(13) . . ?
C8 C9 H9 123.1 . . ?
S1 C9 H9 123.1 . . ?
C6 S1 C9 91.6(5) . . ?
C6 C7A C8A 114.5(12) . . ?
C6 C7A H7A 122.8 . . ?
C8A C7A H7A 122.8 . . ?
C9A C8A C7A 107(2) . . ?
C9A C8A H8A 126.6 . . ?
C7A C8A H8A 126.6 . . ?
C8A C9A S1A 117(2) . . ?
C8A C9A H9A 121.5 . . ?
S1A C9A H9A 121.5 . . ?
C6 S1A C9A 92.1(10) . . ?
O1 C10 O2 123.95(11) . . ?
O1 C10 C1 122.82(11) . . ?
O2 C10 C1 113.22(10) . . ?
O2 C11 C12 110.57(10) . . ?
O2 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C17 C12 C13 118.93(12) . . ?
C17 C12 C11 120.83(11) . . ?
C13 C12 C11 120.24(12) . . ?
C14 C13 C12 120.34(13) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C15 C14 C13 120.23(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.92(13) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.81(13) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.77(12) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?

_refine_diff_density_max         0.373
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.048


####################################################################### 
# 
# 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_er2h
_database_code_depnum_ccdc_archive 'CCDC 2123383'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C34 H22 O6'
_chemical_formula_weight         526.51

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   14.9173(3)
_cell_length_b                   4.73320(10)
_cell_length_c                   18.6755(4)
_cell_angle_alpha                90
_cell_angle_beta                 105.1300(10)
_cell_angle_gamma                90
_cell_volume                     1272.90(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      32.61

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             548
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7105
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            47388
_diffrn_reflns_av_unetI/netI     0.0184
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.563
_diffrn_reflns_theta_max         32.688
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4657
_reflns_number_gt                4077
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Kappa DUO four-circle diffractometer, Bruker Photon3 CPAD. 

 Twofold disorder
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.4176P] 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_number_reflns         4657
_refine_ls_number_parameters     194
_refine_ls_number_restraints     237
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1150
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_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
O1 O 0.32496(4) 1.15478(17) 0.32638(4) 0.02724(16) Uani 1 1 d . . . . .
O2 O 0.45068(4) 1.41821(14) 0.32818(3) 0.01937(13) Uani 1 1 d . . . . .
C1 C 0.45701(5) 1.11806(16) 0.43031(4) 0.01266(13) Uani 1 1 d . . . . .
C2 C 0.41269(5) 0.91097(16) 0.46140(4) 0.01360(13) Uani 1 1 d . . . . .
H2 H 0.352581 0.849975 0.434710 0.016 Uiso 1 1 calc R U . . .
C3 C 0.45349(5) 0.78882(16) 0.53072(4) 0.01253(13) Uani 1 1 d . . . . .
C4 C 0.40153(5) 0.57718(17) 0.55668(4) 0.01456(14) Uani 1 1 d . . . . .
C5 C 0.35355(5) 0.39944(17) 0.57456(4) 0.01568(14) Uani 1 1 d D U . . .
C6 C 0.30384(5) 0.18975(17) 0.60159(4) 0.01640(14) Uani 1 1 d D U . . .
C7 C 0.31880(11) 0.0545(4) 0.66766(9) 0.0237(3) Uani 0.855(3) 1 d D U P A 1
H7 H 0.369755 0.082204 0.709819 0.028 Uiso 0.855(3) 1 calc R U P A 1
C8 C 0.24367(12) -0.1370(2) 0.66185(9) 0.0252(3) Uani 0.855(3) 1 d D U P A 1
H8 H 0.234298 -0.260609 0.699305 0.030 Uiso 0.855(3) 1 calc R U P A 1
C9 C 0.18876(9) -0.1077(3) 0.59286(9) 0.0286(3) Uani 0.855(3) 1 d D U P A 1
H9 H 0.133394 -0.212274 0.573382 0.034 Uiso 0.855(3) 1 calc R U P A 1
O3 O 0.22301(6) 0.0925(2) 0.55424(6) 0.0256(2) Uani 0.855(3) 1 d D U P A 1
C7A C 0.2223(6) 0.047(2) 0.5736(5) 0.0256(2) Uani 0.145(3) 1 d D U P A 2
H7A H 0.181413 0.067702 0.525481 0.031 Uiso 0.145(3) 1 calc R U P A 2
C8A C 0.2109(6) -0.1327(17) 0.6296(6) 0.0286(3) Uani 0.145(3) 1 d D U P A 2
H8A H 0.159787 -0.255566 0.626956 0.034 Uiso 0.145(3) 1 calc R U P A 2
C9A C 0.2832(6) -0.1026(15) 0.6863(5) 0.0252(3) Uani 0.145(3) 1 d D U P A 2
H9A H 0.292745 -0.205733 0.731321 0.030 Uiso 0.145(3) 1 calc R U P A 2
O3A O 0.3418(5) 0.0904(19) 0.6732(4) 0.0237(3) Uani 0.145(3) 1 d D U P A 2
C10 C 0.40323(5) 1.22955(17) 0.35649(4) 0.01530(14) Uani 1 1 d . . . . .
C11 C 0.40472(6) 1.53470(18) 0.25533(4) 0.01895(15) Uani 1 1 d . . . . .
H11A H 0.431950 1.721196 0.249372 0.023 Uiso 1 1 calc R U . . .
H11B H 0.337860 1.562124 0.251580 0.023 Uiso 1 1 calc R U . . .
C12 C 0.41582(6) 1.33958(18) 0.19473(4) 0.01733(15) Uani 1 1 d . . . . .
C13 C 0.34197(6) 1.1741(2) 0.15567(4) 0.02041(16) Uani 1 1 d . . . . .
H13 H 0.283791 1.184793 0.167370 0.024 Uiso 1 1 calc R U . . .
C14 C 0.35251(7) 0.9933(2) 0.09966(5) 0.02547(18) Uani 1 1 d . . . . .
H14 H 0.301708 0.881514 0.073215 0.031 Uiso 1 1 calc R U . . .
C15 C 0.43772(8) 0.9767(2) 0.08254(5) 0.0285(2) Uani 1 1 d . . . . .
H15 H 0.445187 0.853598 0.044338 0.034 Uiso 1 1 calc R U . . .
C16 C 0.51186(8) 1.1404(2) 0.12134(6) 0.0315(2) Uani 1 1 d . . . . .
H16 H 0.570078 1.128670 0.109729 0.038 Uiso 1 1 calc R U . . .
C17 C 0.50101(7) 1.3211(2) 0.17710(6) 0.02548(18) Uani 1 1 d . . . . .
H17 H 0.551886 1.432871 0.203404 0.031 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
O1 C10 1.2091(10) . ?
O2 C10 1.3317(10) . ?
O2 C11 1.4623(9) . ?
C1 C2 1.3912(10) . ?
C1 C3 1.4140(10) 3_676 ?
C1 C10 1.4984(10) . ?
C2 C3 1.4033(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.4267(10) . ?
C4 C5 1.2068(11) . ?
C5 C6 1.4089(11) . ?
C6 C7 1.3560(17) . ?
C6 C7A 1.370(8) . ?
C6 O3 1.3752(12) . ?
C6 O3A 1.392(8) . ?
C7 C8 1.4231(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3414(19) . ?
C8 H8 0.9500 . ?
C9 O3 1.3681(14) . ?
C9 H9 0.9500 . ?
C7A C8A 1.393(10) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.308(11) . ?
C8A H8A 0.9500 . ?
C9A O3A 1.330(9) . ?
C9A H9A 0.9500 . ?
C11 C12 1.5030(12) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.3927(12) . ?
C12 C17 1.3962(12) . ?
C13 C14 1.3919(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.3915(14) . ?
C14 H14 0.9500 . ?
C15 C16 1.3892(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3895(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O2 C11 116.97(6) . . ?
C2 C1 C3 119.50(7) . 3_676 ?
C2 C1 C10 115.69(6) . . ?
C3 C1 C10 124.80(7) 3_676 . ?
C1 C2 C3 122.44(7) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C1 118.06(7) . 3_676 ?
C2 C3 C4 117.36(7) . . ?
C1 C3 C4 124.58(7) 3_676 . ?
C5 C4 C3 176.00(8) . . ?
C4 C5 C6 174.77(8) . . ?
C7 C6 O3 109.60(8) . . ?
C7A C6 O3A 107.4(4) . . ?
C7 C6 C5 132.97(9) . . ?
C7A C6 C5 135.1(3) . . ?
O3 C6 C5 117.42(8) . . ?
O3A C6 C5 117.5(3) . . ?
C6 C7 C8 106.98(12) . . ?
C6 C7 H7 126.5 . . ?
C8 C7 H7 126.5 . . ?
C9 C8 C7 106.19(11) . . ?
C9 C8 H8 126.9 . . ?
C7 C8 H8 126.9 . . ?
C8 C9 O3 111.06(10) . . ?
C8 C9 H9 124.5 . . ?
O3 C9 H9 124.5 . . ?
C9 O3 C6 106.16(9) . . ?
C6 C7A C8A 106.6(7) . . ?
C6 C7A H7A 126.7 . . ?
C8A C7A H7A 126.7 . . ?
C9A C8A C7A 107.8(7) . . ?
C9A C8A H8A 126.1 . . ?
C7A C8A H8A 126.1 . . ?
C8A C9A O3A 111.6(7) . . ?
C8A C9A H9A 124.2 . . ?
O3A C9A H9A 124.2 . . ?
C9A O3A C6 106.7(6) . . ?
O1 C10 O2 124.09(7) . . ?
O1 C10 C1 123.02(7) . . ?
O2 C10 C1 112.89(6) . . ?
O2 C11 C12 110.60(7) . . ?
O2 C11 H11A 109.5 . . ?
C12 C11 H11A 109.5 . . ?
O2 C11 H11B 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 C12 C17 119.04(8) . . ?
C13 C12 C11 120.83(7) . . ?
C17 C12 C11 120.13(8) . . ?
C14 C13 C12 120.69(8) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.76(9) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C16 C15 C14 119.96(9) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.10(9) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C16 C17 C12 120.43(9) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?

_refine_diff_density_max         0.416
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056


####################################################################### 
# 
# 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_ed2h
_database_code_depnum_ccdc_archive 'CCDC 2123386'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C34 H22 N4 O4'
_chemical_formula_weight         550.55

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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.266(5)
_cell_length_b                   4.7151(14)
_cell_length_c                   18.595(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.014(5)
_cell_angle_gamma                90
_cell_volume                     1298.7(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3810
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      26.73

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.015
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5489
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Smart APEX2 CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3
_diffrn_reflns_number            29535
_diffrn_reflns_av_unetI/netI     0.0570
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         30.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3985
_reflns_number_gt                2605
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker X8 Kappa DUO four-circle diffractometer, Bruker APEX2 CCD. 
 The instrument was purchased with the help of funding from the 
 National Science Foundation (NSF) under Grant Number 
 CHE-0946721.  Please acknowledge this grant in all publications 
 of this structure. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0622P)²+0.9062P] 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_number_reflns         3985
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0996
_refine_ls_R_factor_gt           0.0577
_refine_ls_wR_factor_ref         0.1583
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O1 O 0.67188(9) 1.1385(3) 0.67149(7) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.55265(8) 1.4134(3) 0.67372(6) 0.0240(3) Uani 1 1 d . . . . .
N1 N 0.77117(11) 0.1010(4) 0.43763(9) 0.0272(4) Uani 1 1 d . . . . .
N2 N 0.69943(11) -0.1461(4) 0.29779(8) 0.0252(4) Uani 1 1 d . . . . .
C1 C 0.54301(11) 1.1149(4) 0.56960(9) 0.0174(3) Uani 1 1 d . . . . .
C2 C 0.58484(11) 0.9077(4) 0.53669(9) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.643295 0.844355 0.561880 0.022 Uiso 1 1 calc R U . . .
C3 C 0.54392(11) 0.7881(4) 0.46743(9) 0.0175(3) Uani 1 1 d . . . . .
C4 C 0.59407(11) 0.5752(4) 0.43968(9) 0.0196(4) Uani 1 1 d . . . . .
C5 C 0.64106(12) 0.3976(4) 0.42169(9) 0.0208(4) Uani 1 1 d . . . . .
C6 C 0.69062(12) 0.1812(4) 0.39479(9) 0.0203(4) Uani 1 1 d . . . . .
C7 C 0.65574(12) 0.0565(4) 0.32569(9) 0.0241(4) Uani 1 1 d . . . . .
H7 H 0.598559 0.118040 0.297226 0.029 Uiso 1 1 calc R U . . .
C8 C 0.77865(13) -0.2236(4) 0.34059(10) 0.0253(4) Uani 1 1 d . . . . .
H8 H 0.812414 -0.366580 0.323382 0.030 Uiso 1 1 calc R U . . .
C9 C 0.81381(13) -0.1026(5) 0.40966(11) 0.0285(4) Uani 1 1 d . . . . .
H9 H 0.870553 -0.167536 0.438151 0.034 Uiso 1 1 calc R U . . .
C11 C 0.59679(12) 1.2211(4) 0.64344(9) 0.0199(4) Uani 1 1 d . . . . .
C12 C 0.60032(13) 1.5229(4) 0.74691(9) 0.0236(4) Uani 1 1 d . . . . .
H12A H 0.575212 1.710479 0.755053 0.028 Uiso 1 1 calc R U . . .
H12B H 0.665042 1.548451 0.748170 0.028 Uiso 1 1 calc R U . . .
C13 C 0.59128(12) 1.3245(4) 0.80782(9) 0.0217(4) Uani 1 1 d . . . . .
C14 C 0.66450(12) 1.1661(4) 0.84611(10) 0.0248(4) Uani 1 1 d . . . . .
H14 H 0.720721 1.181503 0.833015 0.030 Uiso 1 1 calc R U . . .
C15 C 0.65681(13) 0.9861(5) 0.90306(10) 0.0289(4) Uani 1 1 d . . . . .
H15 H 0.707392 0.879025 0.928916 0.035 Uiso 1 1 calc R U . . .
C16 C 0.57413(15) 0.9631(5) 0.92222(11) 0.0326(5) Uani 1 1 d . . . . .
H16 H 0.568256 0.839733 0.961173 0.039 Uiso 1 1 calc R U . . .
C17 C 0.50089(14) 1.1197(5) 0.88452(11) 0.0334(5) Uani 1 1 d . . . . .
H17 H 0.444825 1.103927 0.897867 0.040 Uiso 1 1 calc R U . . .
C18 C 0.50844(13) 1.3001(5) 0.82725(10) 0.0274(4) Uani 1 1 d . . . . .
H18 H 0.457688 1.406404 0.801387 0.033 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
O1 C11 1.204(2) . ?
O2 C11 1.333(2) . ?
O2 C12 1.473(2) . ?
N1 C9 1.334(2) . ?
N1 C6 1.347(2) . ?
N2 C8 1.328(2) . ?
N2 C7 1.340(2) . ?
C1 C2 1.388(2) . ?
C1 C3 1.415(2) 3_676 ?
C1 C11 1.505(2) . ?
C2 C3 1.406(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.432(2) . ?
C4 C5 1.202(3) . ?
C5 C6 1.431(2) . ?
C6 C7 1.396(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C12 C13 1.501(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.389(3) . ?
C13 C18 1.402(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 O2 C12 116.20(14) . . ?
C9 N1 C6 115.67(16) . . ?
C8 N2 C7 115.51(16) . . ?
C2 C1 C3 119.37(15) . 3_676 ?
C2 C1 C11 115.41(15) . . ?
C3 C1 C11 125.21(15) 3_676 . ?
C1 C2 C3 122.44(16) . . ?
C1 C2 H2 118.8 . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C1 118.19(15) . 3_676 ?
C2 C3 C4 116.96(15) . . ?
C1 C3 C4 124.84(15) 3_676 . ?
C5 C4 C3 174.82(18) . . ?
C4 C5 C6 174.99(19) . . ?
N1 C6 C7 121.06(16) . . ?
N1 C6 C5 118.54(16) . . ?
C7 C6 C5 120.40(16) . . ?
N2 C7 C6 122.83(17) . . ?
N2 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
N2 C8 C9 122.23(18) . . ?
N2 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
N1 C9 C8 122.70(18) . . ?
N1 C9 H9 118.7 . . ?
C8 C9 H9 118.7 . . ?
O1 C11 O2 124.27(16) . . ?
O1 C11 C1 122.65(16) . . ?
O2 C11 C1 113.08(15) . . ?
O2 C12 C13 111.33(15) . . ?
O2 C12 H12A 109.4 . . ?
C13 C12 H12A 109.4 . . ?
O2 C12 H12B 109.4 . . ?
C13 C12 H12B 109.4 . . ?
H12A C12 H12B 108.0 . . ?
C14 C13 C18 119.20(17) . . ?
C14 C13 C12 120.83(16) . . ?
C18 C13 C12 119.96(17) . . ?
C15 C14 C13 121.01(17) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C16 119.49(19) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 119.98(19) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C16 C17 C18 120.61(18) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 119.71(19) . . ?
C17 C18 H18 120.1 . . ?
C13 C18 H18 120.1 . . ?

_refine_diff_density_max         0.447
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.063


####################################################################### 
# 
# 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_ed3h
_database_code_depnum_ccdc_archive 'CCDC 2123388'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C38 H22 N4 O4 S2'
_chemical_formula_weight         662.71

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   6.7871(2)
_cell_length_b                   10.7706(3)
_cell_length_c                   11.4277(2)
_cell_angle_alpha                72.7900(10)
_cell_angle_beta                 82.5830(10)
_cell_angle_gamma                72.8690(10)
_cell_volume                     761.77(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9962
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      33.12

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_F_000             342
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.185
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7225
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            59196
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.868
_diffrn_reflns_theta_max         33.192
_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             5837
_reflns_number_gt                5363
_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       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Bruker D8 Venture Kappa DUO four-circle diffractometer, Bruker Photon3 CPAD. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²+0.2451P] 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_number_reflns         5837
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0325
_refine_ls_wR_factor_ref         0.0919
_refine_ls_wR_factor_gt          0.0896
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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 0.41851(3) 0.22386(2) 0.71934(2) 0.02112(6) Uani 1 1 d . . . . .
O1 O -0.05751(10) 1.10032(7) 0.79033(6) 0.02066(12) Uani 1 1 d . . . . .
O2 O 0.21501(9) 0.91859(6) 0.79597(5) 0.01399(10) Uani 1 1 d . . . . .
N1 N 0.44301(12) 0.14828(7) 0.61335(7) 0.02027(14) Uani 1 1 d . . . . .
N2 N 0.32805(11) 0.37972(7) 0.64512(6) 0.01616(12) Uani 1 1 d . . . . .
C1 C 0.02746(11) 1.00964(7) 0.61638(6) 0.01098(11) Uani 1 1 d . . . . .
C2 C 0.08886(11) 0.88498(7) 0.59044(6) 0.01181(12) Uani 1 1 d . . . . .
H2 H 0.149889 0.806432 0.652324 0.014 Uiso 1 1 calc R U . . .
C3 C 0.06259(11) 0.87277(7) 0.47484(6) 0.01109(11) Uani 1 1 d . . . . .
C4 C 0.12384(11) 0.74127(7) 0.45634(7) 0.01288(12) Uani 1 1 d . . . . .
C5 C 0.17667(11) 0.62713(7) 0.44721(7) 0.01338(12) Uani 1 1 d . . . . .
C6 C 0.24020(11) 0.49550(7) 0.42998(7) 0.01237(12) Uani 1 1 d . . . . .
C7 C 0.23251(13) 0.47394(8) 0.31757(7) 0.01757(14) Uani 1 1 d . . . . .
H7 H 0.180122 0.549041 0.250477 0.021 Uiso 1 1 calc R U . . .
C8 C 0.30085(14) 0.34237(9) 0.29928(8) 0.02077(15) Uani 1 1 d . . . . .
H8 H 0.295163 0.332827 0.219855 0.025 Uiso 1 1 calc R U . . .
C9 C 0.37449(13) 0.22910(8) 0.39228(8) 0.01930(15) Uani 1 1 d . . . . .
H9 H 0.419833 0.142066 0.378580 0.023 Uiso 1 1 calc R U . . .
C10 C 0.38039(12) 0.24690(7) 0.50982(8) 0.01514(13) Uani 1 1 d . . . . .
C11 C 0.31483(11) 0.37917(7) 0.52874(7) 0.01254(12) Uani 1 1 d . . . . .
C12 C 0.05329(11) 1.01725(7) 0.74169(6) 0.01261(12) Uani 1 1 d . . . . .
C13 C 0.25368(12) 0.92523(8) 0.91622(7) 0.01519(13) Uani 1 1 d . . . . .
H13A H 0.137353 0.908734 0.974907 0.018 Uiso 1 1 calc R U . . .
H13B H 0.267565 1.015755 0.910772 0.018 Uiso 1 1 calc R U . . .
C14 C 0.44905(12) 0.81955(8) 0.95881(7) 0.01412(13) Uani 1 1 d . . . . .
C15 C 0.44119(14) 0.69271(9) 1.03413(8) 0.02147(15) Uani 1 1 d . . . . .
H15 H 0.311857 0.672533 1.055134 0.026 Uiso 1 1 calc R U . . .
C16 C 0.62078(17) 0.59537(10) 1.07885(9) 0.02738(19) Uani 1 1 d . . . . .
H16 H 0.614174 0.509328 1.130400 0.033 Uiso 1 1 calc R U . . .
C17 C 0.80984(15) 0.62499(10) 1.04755(9) 0.02691(19) Uani 1 1 d . . . . .
H17 H 0.932619 0.559759 1.079378 0.032 Uiso 1 1 calc R U . . .
C18 C 0.81974(14) 0.74920(11) 0.97016(9) 0.02572(18) Uani 1 1 d . . . . .
H18 H 0.949796 0.767872 0.946942 0.031 Uiso 1 1 calc R U . . .
C19 C 0.63989(13) 0.84701(9) 0.92612(8) 0.01946(15) Uani 1 1 d . . . . .
H19 H 0.647398 0.932519 0.873759 0.023 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 N2 1.6122(7) . ?
S1 N1 1.6152(8) . ?
O1 C12 1.2104(9) . ?
O2 C12 1.3480(9) . ?
O2 C13 1.4576(9) . ?
N1 C10 1.3524(11) . ?
N2 C11 1.3464(10) . ?
C1 C2 1.3922(10) . ?
C1 C3 1.4112(10) 2_576 ?
C1 C12 1.4936(10) . ?
C2 C3 1.4041(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.4252(10) . ?
C4 C5 1.2072(10) . ?
C5 C6 1.4205(10) . ?
C6 C7 1.3812(10) . ?
C6 C11 1.4273(10) . ?
C7 C8 1.4247(11) . ?
C7 H7 0.9500 . ?
C8 C9 1.3705(13) . ?
C8 H8 0.9500 . ?
C9 C10 1.4189(11) . ?
C9 H9 0.9500 . ?
C10 C11 1.4347(10) . ?
C13 C14 1.4968(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C19 1.3928(11) . ?
C14 C15 1.3948(11) . ?
C15 C16 1.3917(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.3897(16) . ?
C16 H16 0.9500 . ?
C17 C18 1.3834(16) . ?
C17 H17 0.9500 . ?
C18 C19 1.3930(13) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 S1 N1 101.77(4) . . ?
C12 O2 C13 114.10(6) . . ?
C10 N1 S1 105.86(6) . . ?
C11 N2 S1 105.66(5) . . ?
C2 C1 C3 119.87(6) . 2_576 ?
C2 C1 C12 119.58(6) . . ?
C3 C1 C12 120.53(6) 2_576 . ?
C1 C2 C3 121.46(6) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C2 C3 C1 118.67(6) . 2_576 ?
C2 C3 C4 118.19(6) . . ?
C1 C3 C4 123.12(6) 2_576 . ?
C5 C4 C3 176.58(8) . . ?
C4 C5 C6 177.11(8) . . ?
C7 C6 C5 121.81(7) . . ?
C7 C6 C11 116.95(7) . . ?
C5 C6 C11 121.24(6) . . ?
C6 C7 C8 121.93(7) . . ?
C6 C7 H7 119.0 . . ?
C8 C7 H7 119.0 . . ?
C9 C8 C7 122.29(8) . . ?
C9 C8 H8 118.9 . . ?
C7 C8 H8 118.9 . . ?
C8 C9 C10 117.41(7) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 H9 121.3 . . ?
N1 C10 C9 126.41(7) . . ?
N1 C10 C11 112.88(7) . . ?
C9 C10 C11 120.71(7) . . ?
N2 C11 C6 125.50(7) . . ?
N2 C11 C10 113.81(7) . . ?
C6 C11 C10 120.68(7) . . ?
O1 C12 O2 123.42(7) . . ?
O1 C12 C1 124.80(7) . . ?
O2 C12 C1 111.78(6) . . ?
O2 C13 C14 108.01(6) . . ?
O2 C13 H13A 110.1 . . ?
C14 C13 H13A 110.1 . . ?
O2 C13 H13B 110.1 . . ?
C14 C13 H13B 110.1 . . ?
H13A C13 H13B 108.4 . . ?
C19 C14 C15 119.20(8) . . ?
C19 C14 C13 120.76(7) . . ?
C15 C14 C13 120.03(7) . . ?
C16 C15 C14 120.72(9) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C17 C16 C15 119.51(9) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C18 C17 C16 120.19(8) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 120.30(9) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C14 C19 C18 120.05(8) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?

_refine_diff_density_max         0.492
_refine_diff_density_min         -0.471
_refine_diff_density_rms         0.055




####################################################################### 
# 
# 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_ed3
_database_code_depnum_ccdc_archive 'CCDC 2123387'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;


# start Validation Reply Form
_vrf_PLAT430_ed3                 
;
PROBLEM: Short Inter D...A Contact  S1       ..O1       .       2.84 Ang.  
RESPONSE: S1 is involved in a disorder.  Quite possibly, the somewhat tight
          contact between S1 and O1 is the driving force behind this 
          disorder.  Nevertheless, oxygen O1 does not show an elongated
          thermal ellipsoid and there is no indication that O1 attempts
          to "get out of the way", so to speak.  
;
# end Validation Reply Form



_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H12 F10 N4 O4 S2'
_chemical_formula_weight         842.64

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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   4.6076(2)
_cell_length_b                   10.9493(4)
_cell_length_c                   31.9883(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.834(3)
_cell_angle_gamma                90
_cell_volume                     1610.20(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9230
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      72.29

_exptl_crystal_description       blade
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.738
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    2.515
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4276
_exptl_absorpt_correction_T_max  0.5533
_exptl_absorpt_process_details   'SADABS (Herbst-Irmer et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   
'I\mS micro-focus sealed tube, multilayer optics'
_diffrn_measurement_device_type  'Bruker Photon3 CPAD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 7.4
_diffrn_reflns_number            34679
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0725
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.384
_diffrn_reflns_theta_max         72.288
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3276
_reflns_number_gt                2740
_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. Completness statistics refer to single and 
 composite reflections containing twin component 1 only. 
;

_computing_data_collection       'APEX3 v2017.3.0 (Bruker-AXS, 2017)'
_computing_cell_refinement       'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.38A (Bruker-AXS, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component pseudo-merohedral twin. 

 Twofold disorder
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0109P)²+1.8423P] 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_number_reflns         3276
_refine_ls_number_parameters     354
_refine_ls_number_restraints     496
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_ref         0.0880
_refine_ls_wR_factor_gt          0.0818
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.2809(5) 0.4447(2) 0.47410(7) 0.0202(5) Uani 1 1 d . . . . .
C2 C 0.4232(5) 0.5481(2) 0.46108(7) 0.0209(5) Uani 1 1 d . . . . .
H2 H 0.368590 0.581216 0.434247 0.025 Uiso 1 1 calc R U . . .
C3 C 0.6440(5) 0.6056(2) 0.48596(7) 0.0201(5) Uani 1 1 d D U . . .
C4 C 0.7767(5) 0.7096(2) 0.46811(7) 0.0227(5) Uani 1 1 d D U . . .
C5 C 0.8490(11) 0.7886(4) 0.44464(14) 0.0218(12) Uani 0.782(3) 1 d D U P A 1
C6 C 0.9269(7) 0.8781(3) 0.41477(10) 0.0213(6) Uani 0.782(3) 1 d D U P A 1
C7 C 0.7914(19) 0.8762(7) 0.3749(2) 0.0288(13) Uani 0.782(3) 1 d D U P A 1
H7 H 0.647427 0.816072 0.368031 0.035 Uiso 0.782(3) 1 calc R U P A 1
C8 C 0.8626(9) 0.9618(3) 0.34405(14) 0.0324(9) Uani 0.782(3) 1 d D U P A 1
H8 H 0.764742 0.956819 0.317007 0.039 Uiso 0.782(3) 1 calc R U P A 1
C9 C 1.0655(14) 1.0512(5) 0.35150(16) 0.0291(11) Uani 0.782(3) 1 d D U P A 1
H9 H 1.111368 1.106905 0.330139 0.035 Uiso 0.782(3) 1 calc R U P A 1
C10 C 1.2051(9) 1.0581(4) 0.39219(12) 0.0223(9) Uani 0.782(3) 1 d D U P A 1
N1 N 1.4073(9) 1.1406(4) 0.40568(12) 0.0245(9) Uani 0.782(3) 1 d D U P A 1
S1 S 1.4968(2) 1.10658(7) 0.45390(2) 0.0241(3) Uani 0.782(3) 1 d D U P A 1
N2 N 1.2927(9) 0.9894(4) 0.46051(15) 0.0229(8) Uani 0.782(3) 1 d D U P A 1
C11 C 1.1401(7) 0.9711(3) 0.42380(9) 0.0205(7) Uani 0.782(3) 1 d . U P A 1
C5A C 0.906(3) 0.7976(13) 0.4552(5) 0.015(3) Uani 0.218(3) 1 d D U P A 2
C6A C 1.036(2) 0.9050(9) 0.4380(4) 0.024(2) Uani 0.218(3) 1 d D U P A 2
C7A C 1.210(4) 0.9847(17) 0.4624(8) 0.031(4) Uani 0.218(3) 1 d D U P A 2
H7A H 1.246892 0.968064 0.491412 0.037 Uiso 0.218(3) 1 calc R U P A 2
C8A C 1.333(4) 1.0899(11) 0.4451(4) 0.032(2) Uani 0.218(3) 1 d D U P A 2
H8A H 1.440786 1.143767 0.463507 0.039 Uiso 0.218(3) 1 calc R U P A 2
C9A C 1.306(4) 1.1190(18) 0.4030(5) 0.024(3) Uani 0.218(3) 1 d D U P A 2
H9A H 1.404255 1.186846 0.391886 0.029 Uiso 0.218(3) 1 calc R U P A 2
C10A C 1.125(3) 1.0421(12) 0.3777(5) 0.019(3) Uani 0.218(3) 1 d D U P A 2
N1A N 1.047(5) 1.0544(17) 0.3370(4) 0.035(3) Uani 0.218(3) 1 d D U P A 2
S1A S 0.8395(11) 0.9421(4) 0.32308(14) 0.0482(13) Uani 0.218(3) 1 d D U P A 2
N2A N 0.825(6) 0.871(2) 0.3666(6) 0.035(4) Uani 0.218(3) 1 d D U P A 2
C11A C 0.994(3) 0.9320(11) 0.3958(4) 0.030(3) Uani 0.218(3) 1 d . . P A 2
C12 C 0.0475(5) 0.3873(2) 0.44584(7) 0.0214(5) Uani 1 1 d . . . . .
O1 O -0.1091(4) 0.30638(15) 0.45538(5) 0.0288(4) Uani 1 1 d . . . . .
O2 O 0.0378(4) 0.43791(15) 0.40713(5) 0.0256(4) Uani 1 1 d . . . . .
C13 C -0.1852(6) 0.3877(2) 0.37769(7) 0.0264(5) Uani 1 1 d . . . . .
H13A H -0.380022 0.396376 0.388652 0.032 Uiso 1 1 calc R U . . .
H13B H -0.148319 0.300064 0.372547 0.032 Uiso 1 1 calc R U . . .
C14 C -0.1662(6) 0.4605(2) 0.33804(7) 0.0256(5) Uani 1 1 d . . . . .
C15 C 0.0243(6) 0.4291(2) 0.30821(8) 0.0284(6) Uani 1 1 d . . . . .
F1 F 0.1977(4) 0.33123(13) 0.31427(5) 0.0356(4) Uani 1 1 d . . . . .
C16 C 0.0502(6) 0.4974(2) 0.27224(8) 0.0319(6) Uani 1 1 d . . . . .
F2 F 0.2405(4) 0.46417(16) 0.24413(5) 0.0422(4) Uani 1 1 d . . . . .
C17 C -0.1173(6) 0.6000(2) 0.26559(7) 0.0328(6) Uani 1 1 d . . . . .
F3 F -0.0936(4) 0.66760(15) 0.23082(5) 0.0460(5) Uani 1 1 d . . . . .
C18 C -0.3107(6) 0.6335(2) 0.29436(8) 0.0314(6) Uani 1 1 d . . . . .
F4 F -0.4811(4) 0.73223(14) 0.28727(5) 0.0410(4) Uani 1 1 d . . . . .
C19 C -0.3321(6) 0.5643(2) 0.33014(7) 0.0267(5) Uani 1 1 d . . . . .
F5 F -0.5253(3) 0.59976(13) 0.35749(4) 0.0327(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.386(3) . ?
C1 C3 1.413(3) 3_666 ?
C1 C12 1.496(3) . ?
C2 C3 1.399(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.429(3) . ?
C4 C5 1.207(5) . ?
C4 C5A 1.221(11) . ?
C5 C6 1.431(5) . ?
C6 C7 1.382(8) . ?
C6 C11 1.431(5) . ?
C7 C8 1.415(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.363(7) . ?
C8 H8 0.9500 . ?
C9 C10 1.415(6) . ?
C9 H9 0.9500 . ?
C10 N1 1.347(5) . ?
C10 C11 1.436(5) . ?
N1 S1 1.613(4) . ?
S1 N2 1.613(4) . ?
N2 C11 1.343(5) . ?
C5A C6A 1.444(13) . ?
C6A C11A 1.385(17) . ?
C6A C7A 1.388(18) . ?
C7A C8A 1.414(17) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.381(16) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.404(15) . ?
C9A H9A 0.9500 . ?
C10A N1A 1.333(13) . ?
C10A C11A 1.483(19) . ?
N1A S1A 1.604(15) . ?
S1A N2A 1.601(16) . ?
N2A C11A 1.35(3) . ?
C12 O1 1.195(3) . ?
C12 O2 1.355(3) . ?
O2 C13 1.454(3) . ?
C13 C14 1.505(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.382(4) . ?
C14 C19 1.384(4) . ?
C15 F1 1.343(3) . ?
C15 C16 1.384(3) . ?
C16 F2 1.347(3) . ?
C16 C17 1.372(4) . ?
C17 F3 1.346(3) . ?
C17 C18 1.373(4) . ?
C18 F4 1.347(3) . ?
C18 C19 1.381(3) . ?
C19 F5 1.346(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
C2 C1 C3 119.9(2) . 3_666 ?
C2 C1 C12 119.8(2) . . ?
C3 C1 C12 120.3(2) 3_666 . ?
C1 C2 C3 122.5(2) . . ?
C1 C2 H2 118.7 . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C1 117.6(2) . 3_666 ?
C2 C3 C4 116.5(2) . . ?
C1 C3 C4 125.9(2) 3_666 . ?
C5 C4 C3 164.3(3) . . ?
C5A C4 C3 175.2(8) . . ?
C4 C5 C6 176.6(4) . . ?
C7 C6 C11 117.3(4) . . ?
C7 C6 C5 119.2(4) . . ?
C11 C6 C5 123.5(3) . . ?
C6 C7 C8 121.5(6) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 H7 119.3 . . ?
C9 C8 C7 122.8(5) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C8 C9 C10 117.6(4) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
N1 C10 C9 126.3(4) . . ?
N1 C10 C11 113.1(3) . . ?
C9 C10 C11 120.6(4) . . ?
C10 N1 S1 106.2(3) . . ?
N2 S1 N1 101.2(2) . . ?
C11 N2 S1 106.2(3) . . ?
N2 C11 C6 126.5(3) . . ?
N2 C11 C10 113.3(3) . . ?
C6 C11 C10 120.2(3) . . ?
C4 C5A C6A 175.0(14) . . ?
C11A C6A C7A 116.9(13) . . ?
C11A C6A C5A 120.7(12) . . ?
C7A C6A C5A 122.4(14) . . ?
C6A C7A C8A 121.6(19) . . ?
C6A C7A H7A 119.2 . . ?
C8A C7A H7A 119.2 . . ?
C9A C8A C7A 123.9(15) . . ?
C9A C8A H8A 118.0 . . ?
C7A C8A H8A 118.0 . . ?
C8A C9A C10A 115.7(14) . . ?
C8A C9A H9A 122.1 . . ?
C10A C9A H9A 122.1 . . ?
N1A C10A C9A 127.8(13) . . ?
N1A C10A C11A 111.9(12) . . ?
C9A C10A C11A 120.4(13) . . ?
C10A N1A S1A 108.1(11) . . ?
N2A S1A N1A 101.1(10) . . ?
C11A N2A S1A 107.6(15) . . ?
N2A C11A C6A 127.2(13) . . ?
N2A C11A C10A 111.4(13) . . ?
C6A C11A C10A 121.3(12) . . ?
O1 C12 O2 123.6(2) . . ?
O1 C12 C1 125.4(2) . . ?
O2 C12 C1 111.03(19) . . ?
C12 O2 C13 114.57(18) . . ?
O2 C13 C14 105.49(18) . . ?
O2 C13 H13A 110.6 . . ?
C14 C13 H13A 110.6 . . ?
O2 C13 H13B 110.6 . . ?
C14 C13 H13B 110.6 . . ?
H13A C13 H13B 108.8 . . ?
C15 C14 C19 116.5(2) . . ?
C15 C14 C13 121.7(2) . . ?
C19 C14 C13 121.8(2) . . ?
F1 C15 C14 119.8(2) . . ?
F1 C15 C16 117.9(2) . . ?
C14 C15 C16 122.3(3) . . ?
F2 C16 C17 120.1(2) . . ?
F2 C16 C15 120.4(3) . . ?
C17 C16 C15 119.5(3) . . ?
F3 C17 C16 120.2(2) . . ?
F3 C17 C18 120.0(3) . . ?
C16 C17 C18 119.9(2) . . ?
F4 C18 C17 119.9(2) . . ?
F4 C18 C19 120.4(3) . . ?
C17 C18 C19 119.7(2) . . ?
F5 C19 C18 117.9(2) . . ?
F5 C19 C14 120.0(2) . . ?
C18 C19 C14 122.2(2) . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.076


####################################################################### 
# 
# 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_ed1
_database_code_depnum_ccdc_archive 'CCDC 2123385'
loop_
_audit_author_name
_audit_author_address
'Peter Mueller'
;MIT
United States of America
;
_audit_update_record             
;
2021-11-21 deposited with the CCDC.	2022-06-16 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         ?
_chemical_formula_sum            'C36 H14 F10 N2 O4'
_chemical_formula_weight         728.49

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   5.8211(5)
_cell_length_b                   7.9754(7)
_cell_length_c                   15.4547(13)
_cell_angle_alpha                87.599(3)
_cell_angle_beta                 88.956(3)
_cell_angle_gamma                88.604(3)
_cell_volume                     716.54(11)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9931
_cell_measurement_theta_min      2.56
_cell_measurement_theta_max      30.09

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.688
_exptl_crystal_F_000             366
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.154
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7162
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube, Triumph monochromator'
_diffrn_measurement_device_type  'Bruker Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4
_diffrn_reflns_number            43653
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.557
_diffrn_reflns_theta_max         30.099
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4206
_reflns_number_gt                3387
_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       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
; 
 'Bruker D8 three-circle diffractometer, Bruker Photon 100 CMOS detector' 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0946P)²+0.3194P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_number_reflns         4206
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1565
_refine_ls_wR_factor_gt          0.1432
_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
F1 F 0.68711(17) 0.42510(12) 0.63176(6) 0.0314(2) Uani 1 1 d . . . . .
F2 F 0.66005(19) 0.63237(14) 0.48916(6) 0.0361(3) Uani 1 1 d . . . . .
F3 F 0.9942(2) 0.85374(13) 0.45243(7) 0.0380(3) Uani 1 1 d . . . . .
F4 F 1.3510(2) 0.88155(14) 0.56289(8) 0.0405(3) Uani 1 1 d . . . . .
F5 F 1.37571(17) 0.67993(14) 0.70592(7) 0.0349(2) Uani 1 1 d . . . . .
O1 O 1.03652(19) 0.30514(14) 0.91000(7) 0.0263(2) Uani 1 1 d . . . . .
O2 O 0.86202(18) 0.47121(13) 0.80926(7) 0.0232(2) Uani 1 1 d . . . . .
N1 N -0.1191(2) 0.93231(17) 0.75686(8) 0.0261(3) Uani 1 1 d . . . . .
C1 C 0.6846(2) 0.44952(16) 0.94668(9) 0.0178(3) Uani 1 1 d . . . . .
C2 C 0.5210(2) 0.56586(17) 0.91602(9) 0.0186(3) Uani 1 1 d . . . . .
H2 H 0.536057 0.611319 0.858445 0.022 Uiso 1 1 calc R U . . .
C3 C 0.3347(2) 0.61800(17) 0.96757(9) 0.0183(3) Uani 1 1 d . . . . .
C4 C 0.1705(2) 0.73215(17) 0.92872(9) 0.0204(3) Uani 1 1 d . . . . .
C5 C 0.0400(2) 0.82103(17) 0.88773(9) 0.0206(3) Uani 1 1 d . . . . .
C6 C -0.1355(2) 0.91907(16) 0.84396(9) 0.0190(3) Uani 1 1 d . . . . .
C7 C -0.3163(3) 0.98986(18) 0.89135(10) 0.0232(3) Uani 1 1 d . . . . .
H7 H -0.320041 0.978543 0.952792 0.028 Uiso 1 1 calc R U . . .
C8 C -0.4915(3) 1.0775(2) 0.84742(11) 0.0271(3) Uani 1 1 d . . . . .
H8 H -0.616096 1.128492 0.877855 0.033 Uiso 1 1 calc R U . . .
C9 C -0.4776(3) 1.0875(2) 0.75786(12) 0.0307(3) Uani 1 1 d . . . . .
H9 H -0.595708 1.143496 0.725374 0.037 Uiso 1 1 calc R U . . .
C10 C -0.2896(3) 1.0151(2) 0.71598(10) 0.0311(4) Uani 1 1 d . . . . .
H10 H -0.281880 1.025090 0.654528 0.037 Uiso 1 1 calc R U . . .
C11 C 0.8804(2) 0.39858(17) 0.88909(9) 0.0188(3) Uani 1 1 d . . . . .
C12 C 1.0483(3) 0.42815(19) 0.75048(10) 0.0239(3) Uani 1 1 d . . . . .
H12A H 1.035102 0.310844 0.732954 0.029 Uiso 1 1 calc R U . . .
H12B H 1.197962 0.439148 0.778891 0.029 Uiso 1 1 calc R U . . .
C13 C 1.0322(3) 0.54630(19) 0.67307(9) 0.0229(3) Uani 1 1 d . . . . .
C14 C 0.8504(3) 0.53958(19) 0.61682(10) 0.0242(3) Uani 1 1 d . . . . .
C15 C 0.8341(3) 0.64478(19) 0.54384(10) 0.0267(3) Uani 1 1 d . . . . .
C16 C 1.0045(3) 0.7579(2) 0.52564(10) 0.0283(3) Uani 1 1 d . . . . .
C17 C 1.1865(3) 0.7699(2) 0.58040(11) 0.0286(3) Uani 1 1 d . . . . .
C18 C 1.1970(3) 0.6649(2) 0.65387(10) 0.0267(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.3442(18) . ?
F2 C15 1.3390(19) . ?
F3 C16 1.3401(18) . ?
F4 C17 1.3396(19) . ?
F5 C18 1.3371(19) . ?
O1 C11 1.2013(17) . ?
O2 C11 1.3457(17) . ?
O2 C12 1.4463(17) . ?
N1 C10 1.332(2) . ?
N1 C6 1.3477(19) . ?
C1 C2 1.3888(18) . ?
C1 C3 1.4131(19) 2_667 ?
C1 C11 1.4922(19) . ?
C2 C3 1.3996(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.4266(18) . ?
C4 C5 1.198(2) . ?
C5 C6 1.4332(19) . ?
C6 C7 1.3930(19) . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.384(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C12 C13 1.494(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.384(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.381(2) . ?
C15 C16 1.375(2) . ?
C16 C17 1.376(3) . ?
C17 C18 1.383(2) . ?

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
C11 O2 C12 114.11(11) . . ?
C10 N1 C6 116.75(13) . . ?
C2 C1 C3 119.64(12) . 2_667 ?
C2 C1 C11 119.69(12) . . ?
C3 C1 C11 120.67(12) 2_667 . ?
C1 C2 C3 121.85(12) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C1 118.51(12) . 2_667 ?
C2 C3 C4 117.48(12) . . ?
C1 C3 C4 123.97(12) 2_667 . ?
C5 C4 C3 172.91(15) . . ?
C4 C5 C6 173.90(15) . . ?
N1 C6 C7 123.24(13) . . ?
N1 C6 C5 116.84(12) . . ?
C7 C6 C5 119.87(13) . . ?
C8 C7 C6 119.10(14) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 117.67(14) . . ?
C9 C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C8 C9 C10 119.35(14) . . ?
C8 C9 H9 120.3 . . ?
C10 C9 H9 120.3 . . ?
N1 C10 C9 123.87(15) . . ?
N1 C10 H10 118.1 . . ?
C9 C10 H10 118.1 . . ?
O1 C11 O2 123.30(13) . . ?
O1 C11 C1 125.29(13) . . ?
O2 C11 C1 111.42(11) . . ?
O2 C12 C13 107.40(11) . . ?
O2 C12 H12A 110.2 . . ?
C13 C12 H12A 110.2 . . ?
O2 C12 H12B 110.2 . . ?
C13 C12 H12B 110.2 . . ?
H12A C12 H12B 108.5 . . ?
C18 C13 C14 117.23(14) . . ?
C18 C13 C12 122.03(14) . . ?
C14 C13 C12 120.73(14) . . ?
F1 C14 C15 118.41(14) . . ?
F1 C14 C13 119.68(13) . . ?
C15 C14 C13 121.88(15) . . ?
F2 C15 C16 120.07(14) . . ?
F2 C15 C14 120.68(15) . . ?
C16 C15 C14 119.19(15) . . ?
F3 C16 C15 119.01(15) . . ?
F3 C16 C17 120.25(15) . . ?
C15 C16 C17 120.72(14) . . ?
F4 C17 C16 120.50(15) . . ?
F4 C17 C18 120.52(16) . . ?
C16 C17 C18 118.98(15) . . ?
F5 C18 C17 117.56(15) . . ?
F5 C18 C13 120.47(14) . . ?
C17 C18 C13 121.97(15) . . ?

_refine_diff_density_max         0.663
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.097


