# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_20210220SM_0m
_database_code_depnum_ccdc_archive 'CCDC 2071533'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H14 N2 O2 S'
_chemical_formula_sum            'C21 H14 N2 O2 S'
_chemical_formula_weight         358.40

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      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                   5.3047(3)
_cell_length_b                   17.3349(9)
_cell_length_c                   17.8096(9)
_cell_angle_alpha                90
_cell_angle_beta                 90.4290(10)
_cell_angle_gamma                90
_cell_volume                     1637.66(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8891
_cell_measurement_theta_min      2.57
_cell_measurement_theta_max      35.39

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.454
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.922
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39669
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.639
_diffrn_reflns_theta_max         36.305
_diffrn_reflns_theta_full        25.242
_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             7917
_reflns_number_gt                5997
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0451P)²+0.8693P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7917
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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 0.15724(5) 0.35623(2) 0.31293(2) 0.01437(6) Uani 1 1 d . . . . .
O1 O 0.31917(18) 0.27458(5) 0.55847(5) 0.01841(17) Uani 1 1 d . . . . .
C1 C 0.3688(2) 0.42360(6) 0.35217(6) 0.01149(17) Uani 1 1 d . . . . .
O2 O 0.98986(17) 0.13532(5) 0.47077(5) 0.01914(17) Uani 1 1 d . . . . .
C2 C 0.3268(2) 0.50233(6) 0.34195(6) 0.01373(18) Uani 1 1 d . . . . .
H2 H 0.192467 0.519371 0.310522 0.016 Uiso 1 1 calc R U . . .
N1 N 0.60367(18) 0.31673(5) 0.40572(5) 0.01139(15) Uani 1 1 d . . . . .
N2 N 0.66622(18) 0.21991(5) 0.50112(5) 0.01304(16) Uani 1 1 d . . . . .
C3 C 0.4813(2) 0.55588(6) 0.37769(6) 0.01445(19) Uani 1 1 d . . . . .
H3 H 0.448130 0.609513 0.372823 0.017 Uiso 1 1 calc R U . . .
C4 C 0.6844(2) 0.53042(6) 0.42055(6) 0.01434(19) Uani 1 1 d . . . . .
H4 H 0.791231 0.566969 0.444626 0.017 Uiso 1 1 calc R U . . .
C10 C 0.5158(2) 0.18020(7) 0.21084(7) 0.0173(2) Uani 1 1 d . . . . .
H10 H 0.495102 0.149677 0.166929 0.021 Uiso 1 1 calc R U . . .
C6 C 0.57159(19) 0.39729(6) 0.39625(6) 0.01050(16) Uani 1 1 d . . . . .
C5 C 0.7336(2) 0.45192(6) 0.42867(6) 0.01293(18) Uani 1 1 d . . . . .
H5 H 0.877571 0.435368 0.456317 0.016 Uiso 1 1 calc R U . . .
C12 C 0.3771(2) 0.28359(6) 0.29128(6) 0.01225(17) Uani 1 1 d . . . . .
C7 C 0.5785(2) 0.26961(6) 0.34104(6) 0.01092(17) Uani 1 1 d . . . . .
C8 C 0.7475(2) 0.21036(6) 0.32460(6) 0.01384(18) Uani 1 1 d . . . . .
H8 H 0.885526 0.200327 0.357448 0.017 Uiso 1 1 calc R U . . .
C13 C 0.4557(2) 0.21956(6) 0.54834(6) 0.01369(18) Uani 1 1 d . . . . .
C9 C 0.7140(2) 0.16595(7) 0.26017(7) 0.0163(2) Uani 1 1 d . . . . .
H9 H 0.828665 0.125275 0.249820 0.020 Uiso 1 1 calc R U . . .
C14 C 0.4476(2) 0.14124(7) 0.58244(6) 0.01451(19) Uani 1 1 d . . . . .
C11 C 0.3477(2) 0.23958(7) 0.22626(6) 0.0162(2) Uani 1 1 d . . . . .
H11 H 0.212745 0.250171 0.192452 0.019 Uiso 1 1 calc R U . . .
C15 C 0.2820(2) 0.11047(8) 0.63422(7) 0.0196(2) Uani 1 1 d . . . . .
H15 H 0.145686 0.139768 0.653528 0.023 Uiso 1 1 calc R U . . .
C16 C 0.3246(3) 0.03430(8) 0.65675(8) 0.0229(2) Uani 1 1 d . . . . .
H16 H 0.214819 0.011206 0.692145 0.027 Uiso 1 1 calc R U . . .
C17 C 0.5250(3) -0.00850(7) 0.62835(8) 0.0222(2) Uani 1 1 d . . . . .
H17 H 0.548000 -0.060309 0.644373 0.027 Uiso 1 1 calc R U . . .
C18 C 0.6928(2) 0.02339(7) 0.57673(7) 0.0188(2) Uani 1 1 d . . . . .
H18 H 0.830071 -0.005469 0.557404 0.023 Uiso 1 1 calc R U . . .
C19 C 0.6495(2) 0.09909(6) 0.55509(6) 0.01437(19) Uani 1 1 d . . . . .
C20 C 0.7959(2) 0.14924(6) 0.50360(6) 0.01393(18) Uani 1 1 d . . . . .
C21 C 0.7629(2) 0.29039(6) 0.46752(6) 0.01345(18) Uani 1 1 d . . . . .
H21A H 0.935483 0.281039 0.448844 0.016 Uiso 1 1 calc R U . . .
H21B H 0.772574 0.331226 0.506302 0.016 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 C1 1.7607(11) . ?
S1 C12 1.7608(11) . ?
O1 C13 1.2118(14) . ?
C1 C2 1.3945(15) . ?
C1 C6 1.4032(15) . ?
O2 C20 1.2117(15) . ?
C2 C3 1.3894(16) . ?
C2 H2 0.9500 . ?
N1 C6 1.4168(14) . ?
N1 C7 1.4177(14) . ?
N1 C21 1.4557(14) . ?
N2 C13 1.4032(15) . ?
N2 C20 1.4054(14) . ?
N2 C21 1.4554(14) . ?
C3 C4 1.3879(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.3930(15) . ?
C4 H4 0.9500 . ?
C10 C9 1.3873(18) . ?
C10 C11 1.3904(18) . ?
C10 H10 0.9500 . ?
C6 C5 1.4004(15) . ?
C5 H5 0.9500 . ?
C12 C11 1.3945(16) . ?
C12 C7 1.4041(15) . ?
C7 C8 1.3957(15) . ?
C8 C9 1.3922(16) . ?
C8 H8 0.9500 . ?
C13 C14 1.4880(16) . ?
C9 H9 0.9500 . ?
C14 C15 1.3855(17) . ?
C14 C19 1.3878(17) . ?
C11 H11 0.9500 . ?
C15 C16 1.3980(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.3982(19) . ?
C17 H17 0.9500 . ?
C18 C19 1.3865(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.4865(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?

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
C1 S1 C12 98.05(5) . . ?
C2 C1 C6 120.80(10) . . ?
C2 C1 S1 119.79(8) . . ?
C6 C1 S1 119.35(8) . . ?
C3 C2 C1 120.07(10) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C6 N1 C7 117.43(9) . . ?
C6 N1 C21 117.88(9) . . ?
C7 N1 C21 118.97(9) . . ?
C13 N2 C20 111.64(9) . . ?
C13 N2 C21 122.30(9) . . ?
C20 N2 C21 124.82(10) . . ?
C4 C3 C2 119.49(10) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.78(10) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C9 C10 C11 119.40(10) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C5 C6 C1 118.45(10) . . ?
C5 C6 N1 123.00(9) . . ?
C1 C6 N1 118.55(9) . . ?
C4 C5 C6 120.27(10) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C11 C12 C7 120.62(10) . . ?
C11 C12 S1 120.21(9) . . ?
C7 C12 S1 119.16(8) . . ?
C8 C7 C12 118.78(10) . . ?
C8 C7 N1 122.52(10) . . ?
C12 C7 N1 118.69(9) . . ?
C9 C8 C7 120.12(11) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
O1 C13 N2 124.40(11) . . ?
O1 C13 C14 129.67(11) . . ?
N2 C13 C14 105.90(9) . . ?
C10 C9 C8 120.97(11) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C15 C14 C19 121.73(11) . . ?
C15 C14 C13 130.03(11) . . ?
C19 C14 C13 108.21(10) . . ?
C10 C11 C12 120.08(11) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C14 C15 C16 116.90(12) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
C17 C16 C15 121.38(12) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.27(12) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 116.87(12) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C14 121.83(11) . . ?
C18 C19 C20 129.70(11) . . ?
C14 C19 C20 108.46(10) . . ?
O2 C20 N2 125.13(10) . . ?
O2 C20 C19 129.09(10) . . ?
N2 C20 C19 105.76(9) . . ?
N2 C21 N1 111.71(9) . . ?
N2 C21 H21A 109.3 . . ?
N1 C21 H21A 109.3 . . ?
N2 C21 H21B 109.3 . . ?
N1 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C2 145.36(9) . . . . ?
C12 S1 C1 C6 -37.49(10) . . . . ?
C6 C1 C2 C3 -2.25(17) . . . . ?
S1 C1 C2 C3 174.86(9) . . . . ?
C1 C2 C3 C4 3.11(17) . . . . ?
C2 C3 C4 C5 -0.61(17) . . . . ?
C2 C1 C6 C5 -1.12(16) . . . . ?
S1 C1 C6 C5 -178.24(8) . . . . ?
C2 C1 C6 N1 179.09(10) . . . . ?
S1 C1 C6 N1 1.97(14) . . . . ?
C7 N1 C6 C5 -135.13(11) . . . . ?
C21 N1 C6 C5 17.98(15) . . . . ?
C7 N1 C6 C1 44.65(14) . . . . ?
C21 N1 C6 C1 -162.24(10) . . . . ?
C3 C4 C5 C6 -2.80(17) . . . . ?
C1 C6 C5 C4 3.62(16) . . . . ?
N1 C6 C5 C4 -176.60(10) . . . . ?
C1 S1 C12 C11 -143.61(9) . . . . ?
C1 S1 C12 C7 37.71(10) . . . . ?
C11 C12 C7 C8 -0.61(16) . . . . ?
S1 C12 C7 C8 178.06(8) . . . . ?
C11 C12 C7 N1 178.81(10) . . . . ?
S1 C12 C7 N1 -2.51(13) . . . . ?
C6 N1 C7 C8 135.03(11) . . . . ?
C21 N1 C7 C8 -17.78(15) . . . . ?
C6 N1 C7 C12 -44.37(14) . . . . ?
C21 N1 C7 C12 162.81(10) . . . . ?
C12 C7 C8 C9 -0.45(16) . . . . ?
N1 C7 C8 C9 -179.85(10) . . . . ?
C20 N2 C13 O1 176.85(11) . . . . ?
C21 N2 C13 O1 8.99(17) . . . . ?
C20 N2 C13 C14 -1.37(12) . . . . ?
C21 N2 C13 C14 -169.23(9) . . . . ?
C11 C10 C9 C8 -0.25(17) . . . . ?
C7 C8 C9 C10 0.89(17) . . . . ?
O1 C13 C14 C15 0.4(2) . . . . ?
N2 C13 C14 C15 178.52(12) . . . . ?
O1 C13 C14 C19 -177.86(12) . . . . ?
N2 C13 C14 C19 0.23(12) . . . . ?
C9 C10 C11 C12 -0.82(17) . . . . ?
C7 C12 C11 C10 1.26(17) . . . . ?
S1 C12 C11 C10 -177.41(9) . . . . ?
C19 C14 C15 C16 -1.14(18) . . . . ?
C13 C14 C15 C16 -179.22(12) . . . . ?
C14 C15 C16 C17 0.07(19) . . . . ?
C15 C16 C17 C18 0.6(2) . . . . ?
C16 C17 C18 C19 -0.29(19) . . . . ?
C17 C18 C19 C14 -0.78(18) . . . . ?
C17 C18 C19 C20 178.10(11) . . . . ?
C15 C14 C19 C18 1.54(18) . . . . ?
C13 C14 C19 C18 180.00(10) . . . . ?
C15 C14 C19 C20 -177.55(10) . . . . ?
C13 C14 C19 C20 0.91(12) . . . . ?
C13 N2 C20 O2 -176.65(11) . . . . ?
C21 N2 C20 O2 -9.15(18) . . . . ?
C13 N2 C20 C19 1.90(12) . . . . ?
C21 N2 C20 C19 169.40(10) . . . . ?
C18 C19 C20 O2 -2.2(2) . . . . ?
C14 C19 C20 O2 176.77(12) . . . . ?
C18 C19 C20 N2 179.30(12) . . . . ?
C14 C19 C20 N2 -1.70(12) . . . . ?
C13 N2 C21 N1 -75.02(13) . . . . ?
C20 N2 C21 N1 118.75(11) . . . . ?
C6 N1 C21 N2 143.62(10) . . . . ?
C7 N1 C21 N2 -63.69(13) . . . . ?

_refine_diff_density_max         0.521
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_20210323SM_0m
_database_code_depnum_ccdc_archive 'CCDC 2072890'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H30 N2 O2 S'
_chemical_formula_sum            'C29 H30 N2 O2 S'
_chemical_formula_weight         470.61

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      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                   5.1088(3)
_cell_length_b                   28.1604(17)
_cell_length_c                   17.0732(10)
_cell_angle_alpha                90
_cell_angle_beta                 98.418(2)
_cell_angle_gamma                90
_cell_volume                     2429.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6681
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      31.36

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.163
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7089
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34987
_diffrn_reflns_av_unetI/netI     0.0551
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -43
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         33.235
_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             9297
_reflns_number_gt                6685
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0472P)²+0.6090P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9297
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1124
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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 0.50387(6) 0.21412(2) 0.89443(2) 0.01560(7) Uani 1 1 d . . . . .
O1 O 0.3848(2) 0.58179(4) 0.24468(6) 0.0294(2) Uani 1 1 d . . . . .
N1 N 0.8927(2) 0.26817(3) 0.81939(5) 0.01280(18) Uani 1 1 d . . . . .
C1 C 0.7548(2) 0.25014(4) 0.94583(7) 0.0125(2) Uani 1 1 d . . . . .
O2 O 1.0317(2) 0.49368(4) 0.15402(6) 0.0241(2) Uani 1 1 d . . . . .
N2 N 0.7283(2) 0.53360(4) 0.21812(6) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.7763(2) 0.25568(4) 1.02765(7) 0.0157(2) Uani 1 1 d . . . . .
H2 H 0.660934 0.238764 1.056518 0.019 Uiso 1 1 calc R U . . .
C3 C 0.9668(2) 0.28600(4) 1.06707(7) 0.0163(2) Uani 1 1 d . . . . .
H3 H 0.978791 0.290630 1.122597 0.020 Uiso 1 1 calc R U . . .
C4 C 1.1392(2) 0.30943(4) 1.02440(7) 0.0156(2) Uani 1 1 d . . . . .
H4 H 1.270845 0.329824 1.051262 0.019 Uiso 1 1 calc R U . . .
C5 C 1.1219(2) 0.30347(4) 0.94302(7) 0.0140(2) Uani 1 1 d . . . . .
H5 H 1.244180 0.319140 0.914931 0.017 Uiso 1 1 calc R U . . .
C6 C 0.9251(2) 0.27449(4) 0.90234(6) 0.0114(2) Uani 1 1 d . . . . .
C7 C 0.8650(2) 0.22079(4) 0.79204(6) 0.0120(2) Uani 1 1 d . . . . .
C8 C 1.0092(2) 0.20226(4) 0.73554(7) 0.0147(2) Uani 1 1 d . . . . .
H8 H 1.134889 0.221628 0.714743 0.018 Uiso 1 1 calc R U . . .
C9 C 0.9699(2) 0.15567(4) 0.70960(7) 0.0166(2) Uani 1 1 d . . . . .
H9 H 1.069326 0.143548 0.671189 0.020 Uiso 1 1 calc R U . . .
C10 C 0.7875(3) 0.12659(4) 0.73892(7) 0.0176(2) Uani 1 1 d . . . . .
H10 H 0.757114 0.095168 0.719469 0.021 Uiso 1 1 calc R U . . .
C11 C 0.6500(2) 0.14417(4) 0.79725(7) 0.0163(2) Uani 1 1 d . . . . .
H11 H 0.529557 0.124235 0.819242 0.020 Uiso 1 1 calc R U . . .
C12 C 0.6878(2) 0.19081(4) 0.82361(7) 0.0132(2) Uani 1 1 d . . . . .
C13 C 0.5170(3) 0.56475(4) 0.19820(7) 0.0182(2) Uani 1 1 d . . . . .
C14 C 0.4938(2) 0.57187(4) 0.11121(7) 0.0163(2) Uani 1 1 d . . . . .
C15 C 0.3127(3) 0.59782(5) 0.06063(8) 0.0216(3) Uani 1 1 d . . . . .
H15 H 0.179955 0.616185 0.080017 0.026 Uiso 1 1 calc R U . . .
C16 C 0.3313(3) 0.59611(5) -0.02002(8) 0.0216(3) Uani 1 1 d . . . . .
H16 H 0.207685 0.613202 -0.056462 0.026 Uiso 1 1 calc R U . . .
C17 C 0.5285(3) 0.56971(5) -0.04768(7) 0.0196(2) Uani 1 1 d . . . . .
H17 H 0.537343 0.569096 -0.102863 0.023 Uiso 1 1 calc R U . . .
C18 C 0.7134(3) 0.54411(5) 0.00376(7) 0.0189(2) Uani 1 1 d . . . . .
H18 H 0.849681 0.526468 -0.015230 0.023 Uiso 1 1 calc R U . . .
C19 C 0.6913(2) 0.54535(4) 0.08349(7) 0.0148(2) Uani 1 1 d . . . . .
C20 C 0.8447(3) 0.52039(4) 0.15248(7) 0.0168(2) Uani 1 1 d . . . . .
C21 C 1.0038(2) 0.30353(4) 0.77050(7) 0.0150(2) Uani 1 1 d . . . . .
H21A H 1.180893 0.292890 0.760750 0.018 Uiso 1 1 calc R U . . .
H21B H 1.025634 0.334053 0.799486 0.018 Uiso 1 1 calc R U . . .
C22 C 0.8273(2) 0.31111(4) 0.69140(7) 0.0155(2) Uani 1 1 d . . . . .
H22A H 0.647543 0.320140 0.701103 0.019 Uiso 1 1 calc R U . . .
H22B H 0.813078 0.280989 0.661172 0.019 Uiso 1 1 calc R U . . .
C23 C 0.9364(3) 0.34977(4) 0.64242(7) 0.0160(2) Uani 1 1 d . . . . .
H23A H 1.109227 0.339259 0.628933 0.019 Uiso 1 1 calc R U . . .
H23B H 0.967190 0.378879 0.674988 0.019 Uiso 1 1 calc R U . . .
C24 C 0.7530(3) 0.36178(4) 0.56598(7) 0.0175(2) Uani 1 1 d . . . . .
H24A H 0.726447 0.333080 0.532256 0.021 Uiso 1 1 calc R U . . .
H24B H 0.578361 0.371647 0.578965 0.021 Uiso 1 1 calc R U . . .
C25 C 0.8657(3) 0.40133(5) 0.52040(7) 0.0225(3) Uani 1 1 d . . . . .
H25A H 1.042549 0.391326 0.509425 0.027 Uiso 1 1 calc R U . . .
H25B H 0.891153 0.429700 0.554930 0.027 Uiso 1 1 calc R U . . .
C26 C 0.7009(3) 0.41577(5) 0.44235(7) 0.0179(2) Uani 1 1 d . . . . .
H26A H 0.518775 0.423525 0.451438 0.022 Uiso 1 1 calc R U . . .
H26B H 0.690877 0.388873 0.404684 0.022 Uiso 1 1 calc R U . . .
C27 C 0.8225(3) 0.45881(5) 0.40671(7) 0.0203(3) Uani 1 1 d . . . . .
H27A H 0.811116 0.486325 0.442152 0.024 Uiso 1 1 calc R U . . .
H27B H 1.012565 0.452264 0.406004 0.024 Uiso 1 1 calc R U . . .
C28 C 0.6978(3) 0.47289(4) 0.32327(7) 0.0173(2) Uani 1 1 d . . . . .
H28A H 0.505135 0.477692 0.321778 0.021 Uiso 1 1 calc R U . . .
H28B H 0.724141 0.447170 0.285676 0.021 Uiso 1 1 calc R U . . .
C29 C 0.8245(3) 0.51862(5) 0.29892(7) 0.0189(2) Uani 1 1 d . . . . .
H29A H 0.790047 0.544305 0.335676 0.023 Uiso 1 1 calc R U . . .
H29B H 1.018402 0.514019 0.304436 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 C12 1.7631(12) . ?
S1 C1 1.7646(12) . ?
O1 C13 1.2139(15) . ?
N1 C6 1.4129(14) . ?
N1 C7 1.4138(15) . ?
N1 C21 1.4661(15) . ?
C1 C2 1.3939(16) . ?
C1 C6 1.4028(16) . ?
O2 C20 1.2134(15) . ?
N2 C13 1.3936(17) . ?
N2 C20 1.3940(15) . ?
N2 C29 1.4573(16) . ?
C2 C3 1.3918(18) . ?
C2 H2 0.9500 . ?
C3 C4 1.3889(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3895(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3980(16) . ?
C5 H5 0.9500 . ?
C7 C8 1.3976(16) . ?
C7 C12 1.4020(16) . ?
C8 C9 1.3899(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3875(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3912(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.3925(16) . ?
C11 H11 0.9500 . ?
C13 C14 1.4862(17) . ?
C14 C15 1.3792(18) . ?
C14 C19 1.3926(17) . ?
C15 C16 1.3949(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3890(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3932(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.3827(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.4916(17) . ?
C21 C22 1.5251(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5269(16) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5289(17) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5196(17) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5236(17) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5285(17) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.5254(17) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.5261(17) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?

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
C12 S1 C1 97.68(5) . . ?
C6 N1 C7 116.19(9) . . ?
C6 N1 C21 119.12(9) . . ?
C7 N1 C21 118.77(9) . . ?
C2 C1 C6 120.78(11) . . ?
C2 C1 S1 120.52(9) . . ?
C6 C1 S1 118.65(8) . . ?
C13 N2 C20 112.21(10) . . ?
C13 N2 C29 123.70(10) . . ?
C20 N2 C29 124.01(11) . . ?
C3 C2 C1 120.02(11) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.33(11) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.99(11) . . ?
C3 C4 H4 119.5 . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 120.20(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.62(10) . . ?
C5 C6 N1 122.81(10) . . ?
C1 C6 N1 118.56(10) . . ?
C8 C7 C12 118.41(10) . . ?
C8 C7 N1 122.89(10) . . ?
C12 C7 N1 118.70(10) . . ?
C9 C8 C7 120.40(11) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 121.04(11) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C11 118.97(11) . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C10 C11 C12 120.41(11) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C7 120.69(11) . . ?
C11 C12 S1 120.67(9) . . ?
C7 C12 S1 118.59(9) . . ?
O1 C13 N2 125.07(12) . . ?
O1 C13 C14 129.00(12) . . ?
N2 C13 C14 105.93(10) . . ?
C15 C14 C19 121.63(11) . . ?
C15 C14 C13 130.19(11) . . ?
C19 C14 C13 108.15(11) . . ?
C14 C15 C16 117.60(12) . . ?
C14 C15 H15 121.2 . . ?
C16 C15 H15 121.2 . . ?
C17 C16 C15 120.78(12) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.42(12) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 117.51(12) . . ?
C19 C18 H18 121.2 . . ?
C17 C18 H18 121.2 . . ?
C18 C19 C14 121.05(11) . . ?
C18 C19 C20 131.02(11) . . ?
C14 C19 C20 107.89(10) . . ?
O2 C20 N2 125.12(11) . . ?
O2 C20 C19 129.06(11) . . ?
N2 C20 C19 105.82(10) . . ?
N1 C21 C22 111.79(10) . . ?
N1 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N1 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C21 C22 C23 111.65(10) . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C23 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C22 C23 C24 113.45(10) . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 111.61(10) . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24B 109.3 . . ?
C23 C24 H24B 109.3 . . ?
H24A C24 H24B 108.0 . . ?
C24 C25 C26 116.17(11) . . ?
C24 C25 H25A 108.2 . . ?
C26 C25 H25A 108.2 . . ?
C24 C25 H25B 108.2 . . ?
C26 C25 H25B 108.2 . . ?
H25A C25 H25B 107.4 . . ?
C25 C26 C27 110.79(11) . . ?
C25 C26 H26A 109.5 . . ?
C27 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C27 C26 H26B 109.5 . . ?
H26A C26 H26B 108.1 . . ?
C28 C27 C26 116.06(11) . . ?
C28 C27 H27A 108.3 . . ?
C26 C27 H27A 108.3 . . ?
C28 C27 H27B 108.3 . . ?
C26 C27 H27B 108.3 . . ?
H27A C27 H27B 107.4 . . ?
C27 C28 C29 109.74(10) . . ?
C27 C28 H28A 109.7 . . ?
C29 C28 H28A 109.7 . . ?
C27 C28 H28B 109.7 . . ?
C29 C28 H28B 109.7 . . ?
H28A C28 H28B 108.2 . . ?
N2 C29 C28 113.86(10) . . ?
N2 C29 H29A 108.8 . . ?
C28 C29 H29A 108.8 . . ?
N2 C29 H29B 108.8 . . ?
C28 C29 H29B 108.8 . . ?
H29A C29 H29B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C2 -143.84(10) . . . . ?
C12 S1 C1 C6 38.63(10) . . . . ?
C6 C1 C2 C3 0.61(18) . . . . ?
S1 C1 C2 C3 -176.86(9) . . . . ?
C1 C2 C3 C4 -1.88(18) . . . . ?
C2 C3 C4 C5 0.81(18) . . . . ?
C3 C4 C5 C6 1.57(18) . . . . ?
C4 C5 C6 C1 -2.80(17) . . . . ?
C4 C5 C6 N1 178.07(11) . . . . ?
C2 C1 C6 C5 1.73(17) . . . . ?
S1 C1 C6 C5 179.25(9) . . . . ?
C2 C1 C6 N1 -179.10(10) . . . . ?
S1 C1 C6 N1 -1.58(14) . . . . ?
C7 N1 C6 C5 132.10(12) . . . . ?
C21 N1 C6 C5 -20.51(16) . . . . ?
C7 N1 C6 C1 -47.04(15) . . . . ?
C21 N1 C6 C1 160.35(11) . . . . ?
C6 N1 C7 C8 -131.86(12) . . . . ?
C21 N1 C7 C8 20.85(16) . . . . ?
C6 N1 C7 C12 47.31(15) . . . . ?
C21 N1 C7 C12 -159.98(11) . . . . ?
C12 C7 C8 C9 2.20(17) . . . . ?
N1 C7 C8 C9 -178.63(11) . . . . ?
C7 C8 C9 C10 0.03(18) . . . . ?
C8 C9 C10 C11 -2.33(18) . . . . ?
C9 C10 C11 C12 2.36(18) . . . . ?
C10 C11 C12 C7 -0.12(18) . . . . ?
C10 C11 C12 S1 177.26(10) . . . . ?
C8 C7 C12 C11 -2.16(17) . . . . ?
N1 C7 C12 C11 178.64(11) . . . . ?
C8 C7 C12 S1 -179.59(9) . . . . ?
N1 C7 C12 S1 1.21(15) . . . . ?
C1 S1 C12 C11 144.17(10) . . . . ?
C1 S1 C12 C7 -38.41(10) . . . . ?
C20 N2 C13 O1 -179.28(13) . . . . ?
C29 N2 C13 O1 -2.3(2) . . . . ?
C20 N2 C13 C14 0.59(14) . . . . ?
C29 N2 C13 C14 177.59(11) . . . . ?
O1 C13 C14 C15 -2.8(2) . . . . ?
N2 C13 C14 C15 177.34(13) . . . . ?
O1 C13 C14 C19 179.31(14) . . . . ?
N2 C13 C14 C19 -0.55(14) . . . . ?
C19 C14 C15 C16 0.9(2) . . . . ?
C13 C14 C15 C16 -176.75(13) . . . . ?
C14 C15 C16 C17 -1.0(2) . . . . ?
C15 C16 C17 C18 0.0(2) . . . . ?
C16 C17 C18 C19 0.9(2) . . . . ?
C17 C18 C19 C14 -1.02(19) . . . . ?
C17 C18 C19 C20 176.33(13) . . . . ?
C15 C14 C19 C18 0.1(2) . . . . ?
C13 C14 C19 C18 178.22(12) . . . . ?
C15 C14 C19 C20 -177.79(12) . . . . ?
C13 C14 C19 C20 0.32(14) . . . . ?
C13 N2 C20 O2 179.94(13) . . . . ?
C29 N2 C20 O2 3.0(2) . . . . ?
C13 N2 C20 C19 -0.40(14) . . . . ?
C29 N2 C20 C19 -177.39(11) . . . . ?
C18 C19 C20 O2 2.1(2) . . . . ?
C14 C19 C20 O2 179.67(13) . . . . ?
C18 C19 C20 N2 -177.58(13) . . . . ?
C14 C19 C20 N2 0.03(14) . . . . ?
C6 N1 C21 C22 -144.07(10) . . . . ?
C7 N1 C21 C22 64.03(14) . . . . ?
N1 C21 C22 C23 177.07(10) . . . . ?
C21 C22 C23 C24 -174.71(10) . . . . ?
C22 C23 C24 C25 178.38(11) . . . . ?
C23 C24 C25 C26 179.12(11) . . . . ?
C24 C25 C26 C27 174.53(12) . . . . ?
C25 C26 C27 C28 172.18(12) . . . . ?
C26 C27 C28 C29 175.21(11) . . . . ?
C13 N2 C29 C28 92.19(15) . . . . ?
C20 N2 C29 C28 -91.16(15) . . . . ?
C27 C28 C29 N2 176.79(11) . . . . ?

_refine_diff_density_max         0.442
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.062

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

data_20210226SM_P
_database_code_depnum_ccdc_archive 'CCDC 2071534'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H18 N2 O2 S'
_chemical_formula_sum            'C23 H18 N2 O2 S'
_chemical_formula_weight         386.45

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   11.0721(2)
_cell_length_b                   8.4129(2)
_cell_length_c                   38.9970(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3632.51(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9769
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      36.26

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_F_000             1616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.201
_shelx_estimated_absorpt_T_min   0.910
_shelx_estimated_absorpt_T_max   0.961
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6969
_exptl_absorpt_correction_T_max  0.7471
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            83350
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0379
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -64
_diffrn_reflns_limit_l_max       64
_diffrn_reflns_theta_min         2.784
_diffrn_reflns_theta_max         36.328
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8792
_reflns_number_gt                7312
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+1.1994P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8792
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0465
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0931
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.45039(2) -0.00445(2) 0.31594(2) 0.01221(4) Uani 1 1 d . . . . .
O1 O 0.72683(6) 0.52345(8) 0.44590(2) 0.01926(12) Uani 1 1 d . . . . .
O2 O 1.05627(6) 0.19910(9) 0.43667(2) 0.02313(14) Uani 1 1 d . . . . .
N1 N 0.64476(6) 0.22602(8) 0.33073(2) 0.01071(10) Uani 1 1 d . . . . .
N2 N 0.88960(6) 0.36348(8) 0.43237(2) 0.01111(11) Uani 1 1 d . . . . .
C1 C 0.43140(7) 0.17415(9) 0.33891(2) 0.01116(12) Uani 1 1 d . . . . .
C2 C 0.31806(7) 0.21574(10) 0.35143(2) 0.01352(13) Uani 1 1 d . . . . .
H2 H 0.250097 0.150779 0.346454 0.016 Uiso 1 1 calc R U . . .
C3 C 0.30393(8) 0.35191(10) 0.37117(2) 0.01622(14) Uani 1 1 d . . . . .
H3 H 0.227583 0.377030 0.380871 0.019 Uiso 1 1 calc R U . . .
C4 C 0.40231(8) 0.45090(10) 0.37659(2) 0.01598(14) Uani 1 1 d . . . . .
H4 H 0.393016 0.544487 0.389958 0.019 Uiso 1 1 calc R U . . .
C5 C 0.51454(7) 0.41414(9) 0.36258(2) 0.01338(13) Uani 1 1 d . . . . .
H5 H 0.580127 0.485736 0.365432 0.016 Uiso 1 1 calc R U . . .
C6 C 0.53160(7) 0.27273(9) 0.34434(2) 0.01026(11) Uani 1 1 d . . . . .
C7 C 0.64177(7) 0.17802(9) 0.29573(2) 0.01080(11) Uani 1 1 d . . . . .
C8 C 0.72302(7) 0.23509(10) 0.27127(2) 0.01407(13) Uani 1 1 d . . . . .
H8 H 0.783294 0.309647 0.277739 0.017 Uiso 1 1 calc R U . . .
C9 C 0.71602(8) 0.18311(11) 0.23741(2) 0.01694(14) Uani 1 1 d . . . . .
H9 H 0.773035 0.220605 0.221105 0.020 Uiso 1 1 calc R U . . .
C10 C 0.62684(8) 0.07726(11) 0.22718(2) 0.01786(15) Uani 1 1 d . . . . .
H10 H 0.622941 0.042288 0.204048 0.021 Uiso 1 1 calc R U . . .
C11 C 0.54323(8) 0.02279(10) 0.25108(2) 0.01524(13) Uani 1 1 d . . . . .
H11 H 0.480320 -0.046972 0.244155 0.018 Uiso 1 1 calc R U . . .
C12 C 0.55196(7) 0.07079(9) 0.28519(2) 0.01146(12) Uani 1 1 d . . . . .
C13 C 0.81016(7) 0.43898(9) 0.45466(2) 0.01212(12) Uani 1 1 d . . . . .
C14 C 0.84850(7) 0.39363(9) 0.48984(2) 0.01285(12) Uani 1 1 d . . . . .
C15 C 0.80167(8) 0.43650(11) 0.52140(2) 0.01817(15) Uani 1 1 d . . . . .
H15 H 0.734765 0.506648 0.523291 0.022 Uiso 1 1 calc R U . . .
C16 C 0.85732(9) 0.37188(13) 0.55037(2) 0.02208(17) Uani 1 1 d . . . . .
H16 H 0.827538 0.398522 0.572486 0.026 Uiso 1 1 calc R U . . .
C17 C 0.95545(9) 0.26929(13) 0.54755(2) 0.02171(17) Uani 1 1 d . . . . .
H17 H 0.991261 0.227156 0.567733 0.026 Uiso 1 1 calc R U . . .
C18 C 1.00219(8) 0.22725(11) 0.51553(2) 0.01873(15) Uani 1 1 d . . . . .
H18 H 1.069209 0.157391 0.513470 0.022 Uiso 1 1 calc R U . . .
C19 C 0.94674(7) 0.29163(10) 0.48698(2) 0.01308(12) Uani 1 1 d . . . . .
C20 C 0.97510(7) 0.27291(10) 0.44993(2) 0.01375(13) Uani 1 1 d . . . . .
C21 C 0.75359(7) 0.30716(10) 0.34317(2) 0.01241(12) Uani 1 1 d . . . . .
H21A H 0.746498 0.422453 0.338509 0.015 Uiso 1 1 calc R U . . .
H21B H 0.824807 0.266775 0.330534 0.015 Uiso 1 1 calc R U . . .
C22 C 0.77256(7) 0.28137(9) 0.38161(2) 0.01195(12) Uani 1 1 d . . . . .
H22A H 0.699275 0.315730 0.394123 0.014 Uiso 1 1 calc R U . . .
H22B H 0.784506 0.166604 0.386076 0.014 Uiso 1 1 calc R U . . .
C23 C 0.88149(7) 0.37357(9) 0.39510(2) 0.01193(12) Uani 1 1 d . . . . .
H23A H 0.956195 0.330033 0.384784 0.014 Uiso 1 1 calc R U . . .
H23B H 0.874545 0.486429 0.388187 0.014 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 C12 1.7617(8) . ?
S1 C1 1.7619(8) . ?
O1 C13 1.2136(10) . ?
O2 C20 1.2087(10) . ?
N1 C6 1.4162(10) . ?
N1 C7 1.4238(9) . ?
N1 C21 1.4674(10) . ?
N2 C13 1.3904(10) . ?
N2 C20 1.3950(10) . ?
N2 C23 1.4586(9) . ?
C1 C2 1.3912(11) . ?
C1 C6 1.4012(10) . ?
C2 C3 1.3891(12) . ?
C2 H2 0.9500 . ?
C3 C4 1.3873(13) . ?
C3 H3 0.9500 . ?
C4 C5 1.3922(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.3989(11) . ?
C5 H5 0.9500 . ?
C7 C8 1.3964(11) . ?
C7 C12 1.4042(10) . ?
C8 C9 1.3929(11) . ?
C8 H8 0.9500 . ?
C9 C10 1.3882(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.3911(12) . ?
C10 H10 0.9500 . ?
C11 C12 1.3936(11) . ?
C11 H11 0.9500 . ?
C13 C14 1.4859(11) . ?
C14 C15 1.3835(11) . ?
C14 C19 1.3899(11) . ?
C15 C16 1.3969(13) . ?
C15 H15 0.9500 . ?
C16 C17 1.3920(15) . ?
C16 H16 0.9500 . ?
C17 C18 1.3971(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.3819(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.4868(11) . ?
C21 C22 1.5291(10) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5274(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?

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
C12 S1 C1 96.65(4) . . ?
C6 N1 C7 114.67(6) . . ?
C6 N1 C21 118.27(6) . . ?
C7 N1 C21 117.90(6) . . ?
C13 N2 C20 111.82(6) . . ?
C13 N2 C23 123.89(6) . . ?
C20 N2 C23 124.26(6) . . ?
C2 C1 C6 120.82(7) . . ?
C2 C1 S1 120.03(6) . . ?
C6 C1 S1 119.15(6) . . ?
C3 C2 C1 120.23(7) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 119.41(8) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 120.51(7) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.59(7) . . ?
C4 C5 H5 119.7 . . ?
C6 C5 H5 119.7 . . ?
C5 C6 C1 118.25(7) . . ?
C5 C6 N1 123.09(7) . . ?
C1 C6 N1 118.66(6) . . ?
C8 C7 C12 118.49(7) . . ?
C8 C7 N1 122.85(7) . . ?
C12 C7 N1 118.64(6) . . ?
C9 C8 C7 120.25(7) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.88(8) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.49(7) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C12 119.85(7) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C7 120.99(7) . . ?
C11 C12 S1 120.09(6) . . ?
C7 C12 S1 118.92(5) . . ?
O1 C13 N2 124.92(7) . . ?
O1 C13 C14 128.87(7) . . ?
N2 C13 C14 106.22(6) . . ?
C15 C14 C19 121.71(7) . . ?
C15 C14 C13 130.34(8) . . ?
C19 C14 C13 107.94(7) . . ?
C14 C15 C16 116.92(8) . . ?
C14 C15 H15 121.5 . . ?
C16 C15 H15 121.5 . . ?
C17 C16 C15 121.43(8) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.12(8) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 117.14(8) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C14 121.66(7) . . ?
C18 C19 C20 130.35(8) . . ?
C14 C19 C20 107.98(7) . . ?
O2 C20 N2 125.11(7) . . ?
O2 C20 C19 128.84(7) . . ?
N2 C20 C19 106.02(6) . . ?
N1 C21 C22 111.77(6) . . ?
N1 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N1 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 107.9 . . ?
C23 C22 C21 111.97(6) . . ?
C23 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N2 C23 C22 111.24(6) . . ?
N2 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
N2 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 S1 C1 C2 140.79(6) . . . . ?
C12 S1 C1 C6 -39.26(6) . . . . ?
C6 C1 C2 C3 -3.52(11) . . . . ?
S1 C1 C2 C3 176.42(6) . . . . ?
C1 C2 C3 C4 3.78(12) . . . . ?
C2 C3 C4 C5 -0.36(12) . . . . ?
C3 C4 C5 C6 -3.38(12) . . . . ?
C4 C5 C6 C1 3.61(11) . . . . ?
C4 C5 C6 N1 -177.35(7) . . . . ?
C2 C1 C6 C5 -0.18(11) . . . . ?
S1 C1 C6 C5 179.88(6) . . . . ?
C2 C1 C6 N1 -179.27(7) . . . . ?
S1 C1 C6 N1 0.79(9) . . . . ?
C7 N1 C6 C5 -130.82(7) . . . . ?
C21 N1 C6 C5 15.44(10) . . . . ?
C7 N1 C6 C1 48.22(9) . . . . ?
C21 N1 C6 C1 -165.52(7) . . . . ?
C6 N1 C7 C8 131.32(8) . . . . ?
C21 N1 C7 C8 -15.06(11) . . . . ?
C6 N1 C7 C12 -47.52(9) . . . . ?
C21 N1 C7 C12 166.09(7) . . . . ?
C12 C7 C8 C9 -1.48(12) . . . . ?
N1 C7 C8 C9 179.68(7) . . . . ?
C7 C8 C9 C10 1.61(13) . . . . ?
C8 C9 C10 C11 0.16(14) . . . . ?
C9 C10 C11 C12 -2.03(13) . . . . ?
C10 C11 C12 C7 2.16(12) . . . . ?
C10 C11 C12 S1 -177.25(7) . . . . ?
C8 C7 C12 C11 -0.40(11) . . . . ?
N1 C7 C12 C11 178.50(7) . . . . ?
C8 C7 C12 S1 179.02(6) . . . . ?
N1 C7 C12 S1 -2.09(10) . . . . ?
C1 S1 C12 C11 -140.81(7) . . . . ?
C1 S1 C12 C7 39.77(7) . . . . ?
C20 N2 C13 O1 -179.26(8) . . . . ?
C23 N2 C13 O1 -1.30(12) . . . . ?
C20 N2 C13 C14 0.37(9) . . . . ?
C23 N2 C13 C14 178.33(7) . . . . ?
O1 C13 C14 C15 -1.09(15) . . . . ?
N2 C13 C14 C15 179.30(9) . . . . ?
O1 C13 C14 C19 178.50(9) . . . . ?
N2 C13 C14 C19 -1.11(9) . . . . ?
C19 C14 C15 C16 -0.31(13) . . . . ?
C13 C14 C15 C16 179.23(8) . . . . ?
C14 C15 C16 C17 0.09(14) . . . . ?
C15 C16 C17 C18 0.10(15) . . . . ?
C16 C17 C18 C19 -0.08(14) . . . . ?
C17 C18 C19 C14 -0.14(13) . . . . ?
C17 C18 C19 C20 179.01(9) . . . . ?
C15 C14 C19 C18 0.34(13) . . . . ?
C13 C14 C19 C18 -179.29(8) . . . . ?
C15 C14 C19 C20 -178.98(8) . . . . ?
C13 C14 C19 C20 1.39(9) . . . . ?
C13 N2 C20 O2 -177.89(9) . . . . ?
C23 N2 C20 O2 4.16(13) . . . . ?
C13 N2 C20 C19 0.46(9) . . . . ?
C23 N2 C20 C19 -177.49(7) . . . . ?
C18 C19 C20 O2 -2.14(16) . . . . ?
C14 C19 C20 O2 177.10(9) . . . . ?
C18 C19 C20 N2 179.59(9) . . . . ?
C14 C19 C20 N2 -1.17(9) . . . . ?
C6 N1 C21 C22 62.16(9) . . . . ?
C7 N1 C21 C22 -152.68(7) . . . . ?
N1 C21 C22 C23 -176.62(6) . . . . ?
C13 N2 C23 C22 -70.83(9) . . . . ?
C20 N2 C23 C22 106.88(8) . . . . ?
C21 C22 C23 N2 173.01(6) . . . . ?

_refine_diff_density_max         0.583
_refine_diff_density_min         -0.370
_refine_diff_density_rms         0.062

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

data_20210219SM_0m
_database_code_depnum_ccdc_archive 'CCDC 2071535'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H22 N2 O2 S'
_chemical_formula_sum            'C25 H22 N2 O2 S'
_chemical_formula_weight         414.50

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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
'-x, -y, -z'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'
'x-1/2, y, -z-1/2'

_cell_length_a                   8.6251(9)
_cell_length_b                   16.0949(17)
_cell_length_c                   29.008(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4027.0(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5692
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.186
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6728
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Fine focus sealed tube'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43282
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_av_R_equivalents  0.0762
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         2.627
_diffrn_reflns_theta_max         29.581
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5637
_reflns_number_gt                4051
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+1.4890P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5637
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0717
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1052
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.46210(5) 0.52139(2) 0.13464(2) 0.02270(10) Uani 1 1 d . . . . .
N1 N 0.52166(14) 0.61419(7) 0.22389(4) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.50005(15) 0.64651(7) 0.42987(4) 0.0182(3) Uani 1 1 d . . . . .
C21 C 0.8099(2) 0.49010(11) 0.52607(6) 0.0312(4) Uani 1 1 d . . . . .
H21 H 0.872136 0.476273 0.551988 0.037 Uiso 1 1 calc R U . . .
O3 O 0.47103(15) 0.53249(7) 0.38177(4) 0.0285(3) Uani 1 1 d . . . . .
O4 O 0.57038(15) 0.73084(7) 0.49067(4) 0.0287(3) Uani 1 1 d . . . . .
C20 C 0.7813(2) 0.42993(10) 0.49279(6) 0.0277(4) Uani 1 1 d . . . . .
H20 H 0.824492 0.375972 0.496146 0.033 Uiso 1 1 calc R U . . .
C5 C 0.38148(18) 0.49827(9) 0.18877(5) 0.0186(3) Uani 1 1 d . . . . .
C19 C 0.68989(19) 0.44811(9) 0.45462(6) 0.0228(3) Uani 1 1 d . . . . .
H19 H 0.670403 0.407586 0.431530 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7499(2) 0.57005(10) 0.52244(6) 0.0275(4) Uani 1 1 d . . . . .
H22 H 0.770889 0.611157 0.545098 0.033 Uiso 1 1 calc R U . . .
C23 C 0.65874(18) 0.58711(9) 0.48457(5) 0.0187(3) Uani 1 1 d . . . . .
C24 C 0.57562(18) 0.66449(9) 0.47097(5) 0.0195(3) Uani 1 1 d . . . . .
C25 C 0.59454(17) 0.64667(9) 0.26575(5) 0.0180(3) Uani 1 1 d . . . . .
H25A H 0.687126 0.678884 0.256403 0.022 Uiso 1 1 calc R U . . .
H25B H 0.631572 0.598744 0.284092 0.022 Uiso 1 1 calc R U . . .
C26 C 0.49645(17) 0.70185(9) 0.29752(5) 0.0189(3) Uani 1 1 d . . . . .
H26A H 0.463017 0.752290 0.280705 0.023 Uiso 1 1 calc R U . . .
H26B H 0.402669 0.671321 0.307529 0.023 Uiso 1 1 calc R U . . .
C27 C 0.59268(18) 0.72638(9) 0.33945(5) 0.0181(3) Uani 1 1 d . . . . .
H27A H 0.675655 0.764866 0.329445 0.022 Uiso 1 1 calc R U . . .
H27B H 0.643087 0.676003 0.352054 0.022 Uiso 1 1 calc R U . . .
C28 C 0.49907(19) 0.76790(9) 0.37777(5) 0.0216(3) Uani 1 1 d . . . . .
H28A H 0.571034 0.797027 0.398885 0.026 Uiso 1 1 calc R U . . .
H28B H 0.429506 0.810044 0.363978 0.026 Uiso 1 1 calc R U . . .
C29 C 0.40203(19) 0.70622(10) 0.40547(5) 0.0219(3) Uani 1 1 d . . . . .
H29A H 0.337706 0.736867 0.428052 0.026 Uiso 1 1 calc R U . . .
H29B H 0.331482 0.676009 0.384405 0.026 Uiso 1 1 calc R U . . .
C18 C 0.62843(18) 0.52713(9) 0.45145(5) 0.0178(3) Uani 1 1 d . . . . .
C6 C 0.27817(19) 0.43217(9) 0.19192(6) 0.0234(3) Uani 1 1 d . . . . .
H6 H 0.242879 0.405291 0.164717 0.028 Uiso 1 1 calc R U . . .
C7 C 0.2267(2) 0.40545(10) 0.23463(6) 0.0262(4) Uani 1 1 d . . . . .
H7 H 0.157257 0.359801 0.236941 0.031 Uiso 1 1 calc R U . . .
C8 C 0.27722(19) 0.44585(9) 0.27378(6) 0.0235(3) Uani 1 1 d . . . . .
H8 H 0.244126 0.426870 0.303190 0.028 Uiso 1 1 calc R U . . .
C17 C 0.52521(19) 0.56428(9) 0.41594(5) 0.0198(3) Uani 1 1 d . . . . .
C16 C 0.48206(17) 0.62967(9) 0.14084(5) 0.0173(3) Uani 1 1 d . . . . .
C9 C 0.37582(18) 0.51387(9) 0.27082(5) 0.0200(3) Uani 1 1 d . . . . .
H9 H 0.408332 0.541199 0.298193 0.024 Uiso 1 1 calc R U . . .
C10 C 0.42795(17) 0.54269(9) 0.22792(5) 0.0170(3) Uani 1 1 d . . . . .
C11 C 0.51789(16) 0.66407(9) 0.18410(5) 0.0162(3) Uani 1 1 d . . . . .
C12 C 0.55082(17) 0.74935(9) 0.18571(6) 0.0192(3) Uani 1 1 d . . . . .
H12 H 0.577354 0.774344 0.214314 0.023 Uiso 1 1 calc R U . . .
C13 C 0.54522(18) 0.79799(10) 0.14600(6) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.568818 0.855546 0.147853 0.027 Uiso 1 1 calc R U . . .
C15 C 0.47288(18) 0.67898(10) 0.10166(5) 0.0208(3) Uani 1 1 d . . . . .
H15 H 0.443918 0.654811 0.073053 0.025 Uiso 1 1 calc R U . . .
C14 C 0.50577(19) 0.76355(10) 0.10397(6) 0.0227(3) Uani 1 1 d . . . . .
H14 H 0.501177 0.797085 0.077055 0.027 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 C5 1.7572(16) . ?
S1 C16 1.7605(15) . ?
N1 C11 1.4064(19) . ?
N1 C10 1.4112(19) . ?
N1 C25 1.4639(18) . ?
N2 C24 1.389(2) . ?
N2 C17 1.4007(19) . ?
N2 C29 1.4625(19) . ?
C21 C20 1.390(2) . ?
C21 C22 1.391(2) . ?
C21 H21 0.9500 . ?
O3 C17 1.2094(19) . ?
O4 C24 1.2120(18) . ?
C20 C19 1.390(2) . ?
C20 H20 0.9500 . ?
C5 C6 1.391(2) . ?
C5 C10 1.401(2) . ?
C19 C18 1.381(2) . ?
C19 H19 0.9500 . ?
C22 C23 1.379(2) . ?
C22 H22 0.9500 . ?
C23 C18 1.387(2) . ?
C23 C24 1.490(2) . ?
C25 C26 1.534(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.525(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C28 1.528(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.527(2) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C18 C17 1.487(2) . ?
C6 C7 1.385(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.389(2) . ?
C8 H8 0.9500 . ?
C16 C15 1.388(2) . ?
C16 C11 1.406(2) . ?
C9 C10 1.402(2) . ?
C9 H9 0.9500 . ?
C11 C12 1.402(2) . ?
C12 C13 1.394(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13 0.9500 . ?
C15 C14 1.392(2) . ?
C15 H15 0.9500 . ?
C14 H14 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
C5 S1 C16 99.04(7) . . ?
C11 N1 C10 121.35(12) . . ?
C11 N1 C25 119.14(12) . . ?
C10 N1 C25 117.93(12) . . ?
C24 N2 C17 111.82(12) . . ?
C24 N2 C29 123.34(13) . . ?
C17 N2 C29 124.81(13) . . ?
C20 C21 C22 121.73(16) . . ?
C20 C21 H21 119.1 . . ?
C22 C21 H21 119.1 . . ?
C21 C20 C19 120.49(15) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C6 C5 C10 121.37(14) . . ?
C6 C5 S1 118.31(12) . . ?
C10 C5 S1 120.22(12) . . ?
C18 C19 C20 117.68(15) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C23 C22 C21 117.19(15) . . ?
C23 C22 H22 121.4 . . ?
C21 C22 H22 121.4 . . ?
C22 C23 C18 121.38(14) . . ?
C22 C23 C24 130.68(14) . . ?
C18 C23 C24 107.93(13) . . ?
O4 C24 N2 124.79(14) . . ?
O4 C24 C23 129.03(15) . . ?
N2 C24 C23 106.18(12) . . ?
N1 C25 C26 117.92(12) . . ?
N1 C25 H25A 107.8 . . ?
C26 C25 H25A 107.8 . . ?
N1 C25 H25B 107.8 . . ?
C26 C25 H25B 107.8 . . ?
H25A C25 H25B 107.2 . . ?
C27 C26 C25 109.21(12) . . ?
C27 C26 H26A 109.8 . . ?
C25 C26 H26A 109.8 . . ?
C27 C26 H26B 109.8 . . ?
C25 C26 H26B 109.8 . . ?
H26A C26 H26B 108.3 . . ?
C26 C27 C28 113.96(13) . . ?
C26 C27 H27A 108.8 . . ?
C28 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C28 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C27 112.84(12) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
N2 C29 C28 111.40(13) . . ?
N2 C29 H29A 109.3 . . ?
C28 C29 H29A 109.3 . . ?
N2 C29 H29B 109.3 . . ?
C28 C29 H29B 109.3 . . ?
H29A C29 H29B 108.0 . . ?
C19 C18 C23 121.51(15) . . ?
C19 C18 C17 130.27(14) . . ?
C23 C18 C17 108.22(13) . . ?
C7 C6 C5 120.13(15) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C6 119.26(15) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 120.94(15) . . ?
C7 C8 H8 119.5 . . ?
C9 C8 H8 119.5 . . ?
O3 C17 N2 125.19(15) . . ?
O3 C17 C18 128.97(14) . . ?
N2 C17 C18 105.83(12) . . ?
C15 C16 C11 121.20(14) . . ?
C15 C16 S1 118.47(12) . . ?
C11 C16 S1 120.16(11) . . ?
C8 C9 C10 120.79(15) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C5 C10 C9 117.33(14) . . ?
C5 C10 N1 120.86(13) . . ?
C9 C10 N1 121.80(14) . . ?
C12 C11 C16 117.37(13) . . ?
C12 C11 N1 121.77(14) . . ?
C16 C11 N1 120.86(13) . . ?
C13 C12 C11 121.00(15) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.84(15) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C16 C15 C14 120.53(15) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C13 C14 C15 119.00(15) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C22 C21 C20 C19 -0.4(3) . . . . ?
C16 S1 C5 C6 148.17(12) . . . . ?
C16 S1 C5 C10 -35.45(13) . . . . ?
C21 C20 C19 C18 -0.6(2) . . . . ?
C20 C21 C22 C23 0.8(3) . . . . ?
C21 C22 C23 C18 -0.1(2) . . . . ?
C21 C22 C23 C24 178.67(16) . . . . ?
C17 N2 C24 O4 -178.82(15) . . . . ?
C29 N2 C24 O4 -0.9(2) . . . . ?
C17 N2 C24 C23 0.72(17) . . . . ?
C29 N2 C24 C23 178.67(13) . . . . ?
C22 C23 C24 O4 0.2(3) . . . . ?
C18 C23 C24 O4 179.16(16) . . . . ?
C22 C23 C24 N2 -179.28(16) . . . . ?
C18 C23 C24 N2 -0.35(17) . . . . ?
C11 N1 C25 C26 84.19(17) . . . . ?
C10 N1 C25 C26 -81.69(16) . . . . ?
N1 C25 C26 C27 178.25(12) . . . . ?
C25 C26 C27 C28 -169.34(12) . . . . ?
C26 C27 C28 C29 75.95(16) . . . . ?
C24 N2 C29 C28 79.52(18) . . . . ?
C17 N2 C29 C28 -102.79(17) . . . . ?
C27 C28 C29 N2 63.52(17) . . . . ?
C20 C19 C18 C23 1.2(2) . . . . ?
C20 C19 C18 C17 -178.54(16) . . . . ?
C22 C23 C18 C19 -0.9(2) . . . . ?
C24 C23 C18 C19 -179.94(14) . . . . ?
C22 C23 C18 C17 178.93(15) . . . . ?
C24 C23 C18 C17 -0.11(17) . . . . ?
C10 C5 C6 C7 -4.2(2) . . . . ?
S1 C5 C6 C7 172.13(12) . . . . ?
C5 C6 C7 C8 0.9(2) . . . . ?
C6 C7 C8 C9 1.5(2) . . . . ?
C24 N2 C17 O3 178.95(15) . . . . ?
C29 N2 C17 O3 1.0(2) . . . . ?
C24 N2 C17 C18 -0.78(17) . . . . ?
C29 N2 C17 C18 -178.70(13) . . . . ?
C19 C18 C17 O3 0.6(3) . . . . ?
C23 C18 C17 O3 -179.18(16) . . . . ?
C19 C18 C17 N2 -179.66(16) . . . . ?
C23 C18 C17 N2 0.53(17) . . . . ?
C5 S1 C16 C15 -150.43(12) . . . . ?
C5 S1 C16 C11 34.21(13) . . . . ?
C7 C8 C9 C10 -0.7(2) . . . . ?
C6 C5 C10 C9 4.9(2) . . . . ?
S1 C5 C10 C9 -171.39(11) . . . . ?
C6 C5 C10 N1 -174.25(13) . . . . ?
S1 C5 C10 N1 9.49(19) . . . . ?
C8 C9 C10 C5 -2.4(2) . . . . ?
C8 C9 C10 N1 176.69(13) . . . . ?
C11 N1 C10 C5 27.9(2) . . . . ?
C25 N1 C10 C5 -166.52(13) . . . . ?
C11 N1 C10 C9 -151.15(14) . . . . ?
C25 N1 C10 C9 14.4(2) . . . . ?
C15 C16 C11 C12 -2.8(2) . . . . ?
S1 C16 C11 C12 172.41(11) . . . . ?
C15 C16 C11 N1 177.76(13) . . . . ?
S1 C16 C11 N1 -7.01(19) . . . . ?
C10 N1 C11 C12 151.40(14) . . . . ?
C25 N1 C11 C12 -14.0(2) . . . . ?
C10 N1 C11 C16 -29.2(2) . . . . ?
C25 N1 C11 C16 165.41(13) . . . . ?
C16 C11 C12 C13 1.2(2) . . . . ?
N1 C11 C12 C13 -179.43(14) . . . . ?
C11 C12 C13 C14 0.5(2) . . . . ?
C11 C16 C15 C14 2.8(2) . . . . ?
S1 C16 C15 C14 -172.48(12) . . . . ?
C12 C13 C14 C15 -0.6(2) . . . . ?
C16 C15 C14 C13 -1.1(2) . . . . ?

_refine_diff_density_max         0.305
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_20210223SM_0m
_database_code_depnum_ccdc_archive 'CCDC 2071536'
loop_
_audit_author_name
_audit_author_address
'Ryan VanderLinden'
;University of Utah
United States of America
;
_audit_update_record             
;
2021-03-19 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C27 H26 N2 O2 S)'
_chemical_formula_sum            'C54 H52 N4 O4 S2'
_chemical_formula_weight         885.11

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   22.7337(7)
_cell_length_b                   21.7598(7)
_cell_length_c                   8.9468(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.5280(10)
_cell_angle_gamma                90
_cell_volume                     4364.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9715
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      35.45

_exptl_crystal_description       IRREGULAR
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             1872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.280
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.7133
_exptl_absorpt_correction_T_max  0.7473
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'FINE FOCUS SEALED TUBE'
_diffrn_measurement_device_type  'BRUKER APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            206090
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0708
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.872
_diffrn_reflns_theta_max         37.066
_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             22264
_reflns_number_gt                15868
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+1.3696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         22264
_refine_ls_number_parameters     577
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1010
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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 -0.05526(2) 0.21650(2) 0.79856(3) 0.01457(5) Uani 1 1 d . . . . .
S2 S 0.42332(2) 0.28601(2) 0.30119(3) 0.01531(5) Uani 1 1 d . . . . .
O1 O 0.17130(4) 0.50687(4) 1.16674(10) 0.02542(17) Uani 1 1 d . . . . .
O2 O 0.25079(4) 0.34504(4) 0.94122(10) 0.02219(16) Uani 1 1 d . . . . .
O3 O 0.75329(4) 0.17516(3) 0.40003(9) 0.02033(15) Uani 1 1 d . . . . .
O4 O 0.66550(4) 0.02426(4) 0.64257(10) 0.02286(16) Uani 1 1 d . . . . .
N1 N -0.00228(4) 0.12407(4) 1.02446(9) 0.01151(13) Uani 1 1 d . . . . .
N2 N 0.21254(4) 0.41768(4) 1.08860(10) 0.01627(15) Uani 1 1 d . . . . .
N3 N 0.48768(3) 0.36883(4) 0.53373(9) 0.01113(13) Uani 1 1 d . . . . .
N4 N 0.71058(4) 0.10943(4) 0.55416(10) 0.01515(14) Uani 1 1 d . . . . .
C1 C -0.02094(4) 0.14764(4) 0.75609(10) 0.01211(15) Uani 1 1 d . . . . .
C2 C -0.01538(5) 0.13423(5) 0.60695(11) 0.01693(17) Uani 1 1 d . . . . .
H2 H -0.032669 0.160745 0.527287 0.020 Uiso 1 1 calc R U . . .
C3 C 0.01546(5) 0.08208(5) 0.57456(11) 0.01818(18) Uani 1 1 d . . . . .
H3 H 0.020365 0.073476 0.473251 0.022 Uiso 1 1 calc R U . . .
C4 C 0.03907(5) 0.04263(4) 0.69112(11) 0.01643(17) Uani 1 1 d . . . . .
H4 H 0.059984 0.006854 0.668970 0.020 Uiso 1 1 calc R U . . .
C5 C 0.03242(4) 0.05493(4) 0.84012(11) 0.01311(15) Uani 1 1 d . . . . .
H5 H 0.047742 0.026921 0.918409 0.016 Uiso 1 1 calc R U . . .
C6 C 0.00325(4) 0.10839(4) 0.87506(10) 0.01071(14) Uani 1 1 d . . . . .
C7 C -0.08887(4) 0.18912(4) 0.94980(10) 0.01119(14) Uani 1 1 d . . . . .
C8 C -0.14476(4) 0.21060(4) 0.96953(11) 0.01420(16) Uani 1 1 d . . . . .
H8 H -0.165878 0.238487 0.898406 0.017 Uiso 1 1 calc R U . . .
C9 C -0.16965(4) 0.19123(4) 1.09342(12) 0.01573(16) Uani 1 1 d . . . . .
H9 H -0.207481 0.206339 1.108104 0.019 Uiso 1 1 calc R U . . .
C10 C -0.13888(4) 0.14963(4) 1.19570(11) 0.01542(16) Uani 1 1 d . . . . .
H10 H -0.155852 0.136308 1.280311 0.019 Uiso 1 1 calc R U . . .
C11 C -0.08344(4) 0.12738(4) 1.17497(11) 0.01297(15) Uani 1 1 d . . . . .
H11 H -0.062991 0.098698 1.245065 0.016 Uiso 1 1 calc R U . . .
C12 C -0.05756(4) 0.14690(4) 1.05180(10) 0.01034(14) Uani 1 1 d . . . . .
C13 C 0.22570(4) 0.39347(4) 0.95312(12) 0.01541(16) Uani 1 1 d . . . . .
C14 C 0.20307(4) 0.43900(4) 0.83316(12) 0.01467(16) Uani 1 1 d . . . . .
C15 C 0.20603(5) 0.43906(5) 0.68017(12) 0.01756(17) Uani 1 1 d . . . . .
H15 H 0.224386 0.406312 0.634836 0.021 Uiso 1 1 calc R U . . .
C16 C 0.18099(5) 0.48914(5) 0.59464(13) 0.02089(19) Uani 1 1 d . . . . .
H16 H 0.182512 0.490831 0.489249 0.025 Uiso 1 1 calc R U . . .
C17 C 0.15383(5) 0.53659(5) 0.66247(14) 0.0229(2) Uani 1 1 d . . . . .
H17 H 0.136627 0.569910 0.601848 0.027 Uiso 1 1 calc R U . . .
C18 C 0.15124(5) 0.53642(5) 0.81709(14) 0.0217(2) Uani 1 1 d . . . . .
H18 H 0.132602 0.568857 0.862840 0.026 Uiso 1 1 calc R U . . .
C19 C 0.17692(4) 0.48707(4) 0.90112(12) 0.01619(17) Uani 1 1 d . . . . .
C20 C 0.18456(4) 0.47476(4) 1.06683(13) 0.01758(18) Uani 1 1 d . . . . .
C21 C 0.04166(4) 0.10238(4) 1.15138(10) 0.01221(15) Uani 1 1 d . . . . .
H21A H 0.075303 0.082718 1.112171 0.015 Uiso 1 1 calc R U . . .
H21B H 0.023116 0.071159 1.209307 0.015 Uiso 1 1 calc R U . . .
C22 C 0.06508(4) 0.15543(4) 1.25614(10) 0.01220(15) Uani 1 1 d . . . . .
H22A H 0.031322 0.175066 1.294949 0.015 Uiso 1 1 calc R U . . .
H22B H 0.092990 0.139185 1.343969 0.015 Uiso 1 1 calc R U . . .
C23 C 0.09704(5) 0.20346(4) 1.17482(11) 0.01518(16) Uani 1 1 d . . . . .
H23A H 0.129920 0.183274 1.133446 0.018 Uiso 1 1 calc R U . . .
H23B H 0.068687 0.220096 1.088351 0.018 Uiso 1 1 calc R U . . .
C24 C 0.12249(4) 0.25645(4) 1.27634(10) 0.01388(15) Uani 1 1 d . . . . .
H24A H 0.089275 0.279611 1.308645 0.017 Uiso 1 1 calc R U . . .
H24B H 0.147545 0.239695 1.368386 0.017 Uiso 1 1 calc R U . . .
C25 C 0.15974(5) 0.30012(4) 1.19781(11) 0.01506(16) Uani 1 1 d . . . . .
H25A H 0.135091 0.315795 1.103922 0.018 Uiso 1 1 calc R U . . .
H25B H 0.193753 0.277270 1.168612 0.018 Uiso 1 1 calc R U . . .
C26 C 0.18349(5) 0.35429(4) 1.29773(11) 0.01597(16) Uani 1 1 d . . . . .
H26A H 0.199601 0.338856 1.400442 0.019 Uiso 1 1 calc R U . . .
H26B H 0.149982 0.382345 1.306877 0.019 Uiso 1 1 calc R U . . .
C27 C 0.23210(5) 0.39048(5) 1.23787(12) 0.01978(19) Uani 1 1 d . . . . .
H27A H 0.246337 0.423652 1.310654 0.024 Uiso 1 1 calc R U . . .
H27B H 0.266203 0.362773 1.232248 0.024 Uiso 1 1 calc R U . . .
C28 C 0.39480(4) 0.31323(4) 0.46084(10) 0.01240(15) Uani 1 1 d . . . . .
C29 C 0.33845(4) 0.29556(4) 0.48621(12) 0.01605(17) Uani 1 1 d . . . . .
H29 H 0.314175 0.270021 0.415040 0.019 Uiso 1 1 calc R U . . .
C30 C 0.31773(4) 0.31531(5) 0.61574(12) 0.01821(18) Uani 1 1 d . . . . .
H30 H 0.279802 0.302256 0.634926 0.022 Uiso 1 1 calc R U . . .
C31 C 0.35257(4) 0.35413(5) 0.71695(12) 0.01690(17) Uani 1 1 d . . . . .
H31 H 0.338092 0.368168 0.804624 0.020 Uiso 1 1 calc R U . . .
C32 C 0.40860(4) 0.37266(4) 0.69096(11) 0.01350(15) Uani 1 1 d . . . . .
H32 H 0.431864 0.399739 0.760238 0.016 Uiso 1 1 calc R U . . .
C33 C 0.43088(4) 0.35168(4) 0.56352(10) 0.01071(14) Uani 1 1 d . . . . .
C34 C 0.49146(4) 0.38760(4) 0.38485(10) 0.01048(14) Uani 1 1 d . . . . .
C35 C 0.52405(4) 0.43920(4) 0.35352(11) 0.01287(15) Uani 1 1 d . . . . .
H35 H 0.542509 0.464642 0.434119 0.015 Uiso 1 1 calc R U . . .
C36 C 0.52955(4) 0.45343(4) 0.20475(11) 0.01486(16) Uani 1 1 d . . . . .
H36 H 0.553143 0.487567 0.184912 0.018 Uiso 1 1 calc R U . . .
C37 C 0.50090(5) 0.41821(5) 0.08519(11) 0.01672(17) Uani 1 1 d . . . . .
H37 H 0.504981 0.428100 -0.016016 0.020 Uiso 1 1 calc R U . . .
C38 C 0.46619(5) 0.36839(4) 0.11417(11) 0.01571(16) Uani 1 1 d . . . . .
H38 H 0.445330 0.345012 0.032527 0.019 Uiso 1 1 calc R U . . .
C39 C 0.46202(4) 0.35279(4) 0.26321(10) 0.01238(15) Uani 1 1 d . . . . .
C40 C 0.68013(4) 0.05330(4) 0.53943(12) 0.01612(17) Uani 1 1 d . . . . .
C41 C 0.67178(4) 0.03765(4) 0.37482(12) 0.01469(16) Uani 1 1 d . . . . .
C42 C 0.64418(5) -0.01223(4) 0.29680(13) 0.01920(19) Uani 1 1 d . . . . .
H42 H 0.624938 -0.042980 0.346668 0.023 Uiso 1 1 calc R U . . .
C43 C 0.64579(5) -0.01547(5) 0.14154(13) 0.0207(2) Uani 1 1 d . . . . .
H43 H 0.627378 -0.049238 0.084800 0.025 Uiso 1 1 calc R U . . .
C44 C 0.67380(5) 0.02974(5) 0.06795(13) 0.01929(19) Uani 1 1 d . . . . .
H44 H 0.674348 0.026174 -0.037641 0.023 Uiso 1 1 calc R U . . .
C45 C 0.70107(5) 0.08021(5) 0.14768(12) 0.01745(17) Uani 1 1 d . . . . .
H45 H 0.720091 0.111308 0.098380 0.021 Uiso 1 1 calc R U . . .
C46 C 0.69925(4) 0.08305(4) 0.30136(11) 0.01378(16) Uani 1 1 d . . . . .
C47 C 0.72492(4) 0.12920(4) 0.41634(12) 0.01459(16) Uani 1 1 d . . . . .
C48 C 0.53335(4) 0.38891(4) 0.65910(10) 0.01177(14) Uani 1 1 d . . . . .
H48A H 0.517843 0.423945 0.711537 0.014 Uiso 1 1 calc R U . . .
H48B H 0.568866 0.403254 0.618318 0.014 Uiso 1 1 calc R U . . .
C49 C 0.55156(4) 0.33718(4) 0.77286(10) 0.01176(14) Uani 1 1 d . . . . .
H49A H 0.579335 0.353745 0.860549 0.014 Uiso 1 1 calc R U . . .
H49B H 0.515690 0.321884 0.810498 0.014 Uiso 1 1 calc R U . . .
C50 C 0.58152(4) 0.28364(4) 0.70452(10) 0.01298(15) Uani 1 1 d . . . . .
H50A H 0.553188 0.265914 0.619497 0.016 Uiso 1 1 calc R U . . .
H50B H 0.616507 0.299156 0.663248 0.016 Uiso 1 1 calc R U . . .
C51 C 0.60173(4) 0.23341(4) 0.82061(11) 0.01346(15) Uani 1 1 d . . . . .
H51A H 0.566346 0.217639 0.859680 0.016 Uiso 1 1 calc R U . . .
H51B H 0.628774 0.251921 0.906982 0.016 Uiso 1 1 calc R U . . .
C52 C 0.63378(4) 0.17909(4) 0.76038(11) 0.01516(16) Uani 1 1 d . . . . .
H52A H 0.636825 0.145074 0.834739 0.018 Uiso 1 1 calc R U . . .
H52B H 0.609596 0.164361 0.664847 0.018 Uiso 1 1 calc R U . . .
C53 C 0.69619(4) 0.19526(4) 0.73092(12) 0.01594(17) Uani 1 1 d . . . . .
H53A H 0.692530 0.223857 0.643801 0.019 Uiso 1 1 calc R U . . .
H53B H 0.717814 0.217058 0.820637 0.019 Uiso 1 1 calc R U . . .
C54 C 0.73302(5) 0.13987(5) 0.69783(12) 0.01811(18) Uani 1 1 d . . . . .
H54A H 0.774534 0.153408 0.696826 0.022 Uiso 1 1 calc R U . . .
H54B H 0.733910 0.109714 0.781019 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
S1 C1 1.7597(9) . ?
S1 C7 1.7640(9) . ?
S2 C39 1.7606(9) . ?
S2 C28 1.7657(10) . ?
O1 C20 1.2113(13) . ?
O2 C13 1.2114(12) . ?
O3 C47 1.2118(12) . ?
O4 C40 1.2095(13) . ?
N1 C6 1.4051(12) . ?
N1 C12 1.4100(12) . ?
N1 C21 1.4609(12) . ?
N2 C20 1.3943(13) . ?
N2 C13 1.3987(13) . ?
N2 C27 1.4612(14) . ?
N3 C34 1.4094(11) . ?
N3 C33 1.4110(12) . ?
N3 C48 1.4635(12) . ?
N4 C47 1.3946(13) . ?
N4 C40 1.3993(13) . ?
N4 C54 1.4609(13) . ?
C1 C2 1.3919(13) . ?
C1 C6 1.4040(12) . ?
C2 C3 1.3894(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3883(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.3923(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.3997(12) . ?
C5 H5 0.9500 . ?
C7 C8 1.3922(13) . ?
C7 C12 1.4031(12) . ?
C8 C9 1.3907(14) . ?
C8 H8 0.9500 . ?
C9 C10 1.3908(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.3909(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3984(13) . ?
C11 H11 0.9500 . ?
C13 C14 1.4883(14) . ?
C14 C15 1.3816(15) . ?
C14 C19 1.3918(14) . ?
C15 C16 1.3974(14) . ?
C15 H15 0.9500 . ?
C16 C17 1.3927(17) . ?
C16 H16 0.9500 . ?
C17 C18 1.3943(17) . ?
C17 H17 0.9500 . ?
C18 C19 1.3835(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.4882(15) . ?
C21 C22 1.5262(13) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.5246(13) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.5217(13) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5201(13) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5233(13) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5245(14) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.3917(14) . ?
C28 C33 1.4027(13) . ?
C29 C30 1.3893(15) . ?
C29 H29 0.9500 . ?
C30 C31 1.3869(15) . ?
C30 H30 0.9500 . ?
C31 C32 1.3919(14) . ?
C31 H31 0.9500 . ?
C32 C33 1.3987(13) . ?
C32 H32 0.9500 . ?
C34 C35 1.3989(12) . ?
C34 C39 1.4018(12) . ?
C35 C36 1.3922(13) . ?
C35 H35 0.9500 . ?
C36 C37 1.3874(14) . ?
C36 H36 0.9500 . ?
C37 C38 1.3904(14) . ?
C37 H37 0.9500 . ?
C38 C39 1.3943(13) . ?
C38 H38 0.9500 . ?
C40 C41 1.4928(15) . ?
C41 C42 1.3835(14) . ?
C41 C46 1.3907(13) . ?
C42 C43 1.3974(16) . ?
C42 H42 0.9500 . ?
C43 C44 1.3948(16) . ?
C43 H43 0.9500 . ?
C44 C45 1.3975(14) . ?
C44 H44 0.9500 . ?
C45 C46 1.3837(14) . ?
C45 H45 0.9500 . ?
C46 C47 1.4861(13) . ?
C48 C49 1.5280(12) . ?
C48 H48A 0.9900 . ?
C48 H48B 0.9900 . ?
C49 C50 1.5274(13) . ?
C49 H49A 0.9900 . ?
C49 H49B 0.9900 . ?
C50 C51 1.5253(13) . ?
C50 H50A 0.9900 . ?
C50 H50B 0.9900 . ?
C51 C52 1.5325(13) . ?
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.5265(14) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?
C53 C54 1.5243(14) . ?
C53 H53A 0.9900 . ?
C53 H53B 0.9900 . ?
C54 H54A 0.9900 . ?
C54 H54B 0.9900 . ?

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
C1 S1 C7 98.16(4) . . ?
C39 S2 C28 98.14(4) . . ?
C6 N1 C12 118.24(7) . . ?
C6 N1 C21 120.25(7) . . ?
C12 N1 C21 119.56(7) . . ?
C20 N2 C13 111.87(8) . . ?
C20 N2 C27 123.46(9) . . ?
C13 N2 C27 124.27(9) . . ?
C34 N3 C33 117.13(7) . . ?
C34 N3 C48 119.43(7) . . ?
C33 N3 C48 119.30(7) . . ?
C47 N4 C40 111.74(8) . . ?
C47 N4 C54 122.64(8) . . ?
C40 N4 C54 125.02(9) . . ?
C2 C1 C6 120.86(8) . . ?
C2 C1 S1 119.96(7) . . ?
C6 C1 S1 119.10(7) . . ?
C3 C2 C1 120.01(9) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C4 C3 C2 119.61(9) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.71(9) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 120.27(9) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 118.48(8) . . ?
C5 C6 N1 122.31(8) . . ?
C1 C6 N1 119.21(8) . . ?
C8 C7 C12 120.84(8) . . ?
C8 C7 S1 120.27(7) . . ?
C12 C7 S1 118.85(7) . . ?
C9 C8 C7 119.97(9) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C8 C9 C10 119.67(9) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.46(9) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 120.54(9) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C11 C12 C7 118.50(8) . . ?
C11 C12 N1 122.22(8) . . ?
C7 C12 N1 119.25(8) . . ?
O2 C13 N2 125.12(10) . . ?
O2 C13 C14 128.85(10) . . ?
N2 C13 C14 106.04(8) . . ?
C15 C14 C19 121.76(9) . . ?
C15 C14 C13 130.35(9) . . ?
C19 C14 C13 107.87(9) . . ?
C14 C15 C16 117.46(10) . . ?
C14 C15 H15 121.3 . . ?
C16 C15 H15 121.3 . . ?
C17 C16 C15 120.62(11) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.66(10) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 117.25(10) . . ?
C19 C18 H18 121.4 . . ?
C17 C18 H18 121.4 . . ?
C18 C19 C14 121.23(10) . . ?
C18 C19 C20 130.56(10) . . ?
C14 C19 C20 108.18(8) . . ?
O1 C20 N2 125.05(10) . . ?
O1 C20 C19 128.98(10) . . ?
N2 C20 C19 105.95(8) . . ?
N1 C21 C22 110.92(7) . . ?
N1 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N1 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 111.76(7) . . ?
C23 C22 H22A 109.3 . . ?
C21 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C24 C23 C22 113.50(8) . . ?
C24 C23 H23A 108.9 . . ?
C22 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 112.56(8) . . ?
C25 C24 H24A 109.1 . . ?
C23 C24 H24A 109.1 . . ?
C25 C24 H24B 109.1 . . ?
C23 C24 H24B 109.1 . . ?
H24A C24 H24B 107.8 . . ?
C24 C25 C26 112.51(8) . . ?
C24 C25 H25A 109.1 . . ?
C26 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
C26 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 C27 113.62(8) . . ?
C25 C26 H26A 108.8 . . ?
C27 C26 H26A 108.8 . . ?
C25 C26 H26B 108.8 . . ?
C27 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
N2 C27 C26 113.68(8) . . ?
N2 C27 H27A 108.8 . . ?
C26 C27 H27A 108.8 . . ?
N2 C27 H27B 108.8 . . ?
C26 C27 H27B 108.8 . . ?
H27A C27 H27B 107.7 . . ?
C29 C28 C33 120.82(9) . . ?
C29 C28 S2 120.70(7) . . ?
C33 C28 S2 118.46(7) . . ?
C30 C29 C28 119.93(9) . . ?
C30 C29 H29 120.0 . . ?
C28 C29 H29 120.0 . . ?
C31 C30 C29 119.81(9) . . ?
C31 C30 H30 120.1 . . ?
C29 C30 H30 120.1 . . ?
C30 C31 C32 120.46(9) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C33 120.43(9) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C28 118.50(8) . . ?
C32 C33 N3 122.26(8) . . ?
C28 C33 N3 119.22(8) . . ?
C35 C34 C39 118.60(8) . . ?
C35 C34 N3 122.63(8) . . ?
C39 C34 N3 118.76(8) . . ?
C36 C35 C34 120.30(9) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C37 C36 C35 120.61(9) . . ?
C37 C36 H36 119.7 . . ?
C35 C36 H36 119.7 . . ?
C36 C37 C38 119.69(9) . . ?
C36 C37 H37 120.2 . . ?
C38 C37 H37 120.2 . . ?
C37 C38 C39 119.92(9) . . ?
C37 C38 H38 120.0 . . ?
C39 C38 H38 120.0 . . ?
C38 C39 C34 120.77(8) . . ?
C38 C39 S2 120.05(7) . . ?
C34 C39 S2 119.06(7) . . ?
O4 C40 N4 125.33(10) . . ?
O4 C40 C41 128.86(9) . . ?
N4 C40 C41 105.79(8) . . ?
C42 C41 C46 121.37(10) . . ?
C42 C41 C40 130.52(9) . . ?
C46 C41 C40 108.09(8) . . ?
C41 C42 C43 117.17(10) . . ?
C41 C42 H42 121.4 . . ?
C43 C42 H42 121.4 . . ?
C44 C43 C42 121.52(9) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 120.79(10) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C46 C45 C44 117.30(10) . . ?
C46 C45 H45 121.4 . . ?
C44 C45 H45 121.4 . . ?
C45 C46 C41 121.84(9) . . ?
C45 C46 C47 130.17(9) . . ?
C41 C46 C47 107.97(9) . . ?
O3 C47 N4 124.61(9) . . ?
O3 C47 C46 129.06(10) . . ?
N4 C47 C46 106.33(8) . . ?
N3 C48 C49 111.73(7) . . ?
N3 C48 H48A 109.3 . . ?
C49 C48 H48A 109.3 . . ?
N3 C48 H48B 109.3 . . ?
C49 C48 H48B 109.3 . . ?
H48A C48 H48B 107.9 . . ?
C50 C49 C48 112.64(7) . . ?
C50 C49 H49A 109.1 . . ?
C48 C49 H49A 109.1 . . ?
C50 C49 H49B 109.1 . . ?
C48 C49 H49B 109.1 . . ?
H49A C49 H49B 107.8 . . ?
C51 C50 C49 112.21(7) . . ?
C51 C50 H50A 109.2 . . ?
C49 C50 H50A 109.2 . . ?
C51 C50 H50B 109.2 . . ?
C49 C50 H50B 109.2 . . ?
H50A C50 H50B 107.9 . . ?
C50 C51 C52 114.86(8) . . ?
C50 C51 H51A 108.6 . . ?
C52 C51 H51A 108.6 . . ?
C50 C51 H51B 108.6 . . ?
C52 C51 H51B 108.6 . . ?
H51A C51 H51B 107.5 . . ?
C53 C52 C51 113.12(8) . . ?
C53 C52 H52A 109.0 . . ?
C51 C52 H52A 109.0 . . ?
C53 C52 H52B 109.0 . . ?
C51 C52 H52B 109.0 . . ?
H52A C52 H52B 107.8 . . ?
C54 C53 C52 114.04(8) . . ?
C54 C53 H53A 108.7 . . ?
C52 C53 H53A 108.7 . . ?
C54 C53 H53B 108.7 . . ?
C52 C53 H53B 108.7 . . ?
H53A C53 H53B 107.6 . . ?
N4 C54 C53 113.98(8) . . ?
N4 C54 H54A 108.8 . . ?
C53 C54 H54A 108.8 . . ?
N4 C54 H54B 108.8 . . ?
C53 C54 H54B 108.8 . . ?
H54A C54 H54B 107.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 S1 C1 C2 146.28(8) . . . . ?
C7 S1 C1 C6 -36.99(8) . . . . ?
C6 C1 C2 C3 -1.30(15) . . . . ?
S1 C1 C2 C3 175.38(8) . . . . ?
C1 C2 C3 C4 1.90(15) . . . . ?
C2 C3 C4 C5 -0.32(15) . . . . ?
C3 C4 C5 C6 -1.89(15) . . . . ?
C4 C5 C6 C1 2.46(13) . . . . ?
C4 C5 C6 N1 -177.20(9) . . . . ?
C2 C1 C6 C5 -0.88(14) . . . . ?
S1 C1 C6 C5 -177.59(7) . . . . ?
C2 C1 C6 N1 178.78(9) . . . . ?
S1 C1 C6 N1 2.08(12) . . . . ?
C12 N1 C6 C5 -137.33(9) . . . . ?
C21 N1 C6 C5 26.69(13) . . . . ?
C12 N1 C6 C1 43.01(12) . . . . ?
C21 N1 C6 C1 -152.96(8) . . . . ?
C1 S1 C7 C8 -143.63(8) . . . . ?
C1 S1 C7 C12 38.25(8) . . . . ?
C12 C7 C8 C9 1.40(14) . . . . ?
S1 C7 C8 C9 -176.69(7) . . . . ?
C7 C8 C9 C10 -1.05(14) . . . . ?
C8 C9 C10 C11 0.08(14) . . . . ?
C9 C10 C11 C12 0.56(14) . . . . ?
C10 C11 C12 C7 -0.22(13) . . . . ?
C10 C11 C12 N1 -178.10(8) . . . . ?
C8 C7 C12 C11 -0.75(13) . . . . ?
S1 C7 C12 C11 177.36(7) . . . . ?
C8 C7 C12 N1 177.19(8) . . . . ?
S1 C7 C12 N1 -4.69(11) . . . . ?
C6 N1 C12 C11 136.33(9) . . . . ?
C21 N1 C12 C11 -27.81(12) . . . . ?
C6 N1 C12 C7 -41.53(11) . . . . ?
C21 N1 C12 C7 154.32(8) . . . . ?
C20 N2 C13 O2 178.76(10) . . . . ?
C27 N2 C13 O2 5.84(16) . . . . ?
C20 N2 C13 C14 -0.98(11) . . . . ?
C27 N2 C13 C14 -173.91(8) . . . . ?
O2 C13 C14 C15 -2.02(18) . . . . ?
N2 C13 C14 C15 177.71(10) . . . . ?
O2 C13 C14 C19 179.28(10) . . . . ?
N2 C13 C14 C19 -0.99(10) . . . . ?
C19 C14 C15 C16 -0.78(15) . . . . ?
C13 C14 C15 C16 -179.32(10) . . . . ?
C14 C15 C16 C17 -0.49(15) . . . . ?
C15 C16 C17 C18 0.84(16) . . . . ?
C16 C17 C18 C19 0.10(16) . . . . ?
C17 C18 C19 C14 -1.37(15) . . . . ?
C17 C18 C19 C20 176.33(10) . . . . ?
C15 C14 C19 C18 1.76(15) . . . . ?
C13 C14 C19 C18 -179.41(9) . . . . ?
C15 C14 C19 C20 -176.40(9) . . . . ?
C13 C14 C19 C20 2.43(10) . . . . ?
C13 N2 C20 O1 -175.99(10) . . . . ?
C27 N2 C20 O1 -2.99(16) . . . . ?
C13 N2 C20 C19 2.43(11) . . . . ?
C27 N2 C20 C19 175.42(8) . . . . ?
C18 C19 C20 O1 -2.60(18) . . . . ?
C14 C19 C20 O1 175.33(10) . . . . ?
C18 C19 C20 N2 179.07(10) . . . . ?
C14 C19 C20 N2 -3.00(10) . . . . ?
C6 N1 C21 C22 129.29(8) . . . . ?
C12 N1 C21 C22 -66.89(10) . . . . ?
N1 C21 C22 C23 -62.08(10) . . . . ?
C21 C22 C23 C24 -178.55(8) . . . . ?
C22 C23 C24 C25 173.88(8) . . . . ?
C23 C24 C25 C26 178.10(8) . . . . ?
C24 C25 C26 C27 166.65(9) . . . . ?
C20 N2 C27 C26 86.04(12) . . . . ?
C13 N2 C27 C26 -101.83(11) . . . . ?
C25 C26 C27 N2 60.87(12) . . . . ?
C39 S2 C28 C29 144.17(8) . . . . ?
C39 S2 C28 C33 -37.54(8) . . . . ?
C33 C28 C29 C30 -0.98(14) . . . . ?
S2 C28 C29 C30 177.27(7) . . . . ?
C28 C29 C30 C31 1.99(14) . . . . ?
C29 C30 C31 C32 -1.06(15) . . . . ?
C30 C31 C32 C33 -0.91(14) . . . . ?
C31 C32 C33 C28 1.90(13) . . . . ?
C31 C32 C33 N3 -179.34(8) . . . . ?
C29 C28 C33 C32 -0.96(13) . . . . ?
S2 C28 C33 C32 -179.24(7) . . . . ?
C29 C28 C33 N3 -179.76(8) . . . . ?
S2 C28 C33 N3 1.96(11) . . . . ?
C34 N3 C33 C32 -133.64(9) . . . . ?
C48 N3 C33 C32 23.37(12) . . . . ?
C34 N3 C33 C28 45.11(11) . . . . ?
C48 N3 C33 C28 -157.87(8) . . . . ?
C33 N3 C34 C35 135.62(9) . . . . ?
C48 N3 C34 C35 -21.36(13) . . . . ?
C33 N3 C34 C39 -45.20(11) . . . . ?
C48 N3 C34 C39 157.82(8) . . . . ?
C39 C34 C35 C36 -3.40(13) . . . . ?
N3 C34 C35 C36 175.78(8) . . . . ?
C34 C35 C36 C37 2.61(14) . . . . ?
C35 C36 C37 C38 0.25(15) . . . . ?
C36 C37 C38 C39 -2.24(15) . . . . ?
C37 C38 C39 C34 1.40(14) . . . . ?
C37 C38 C39 S2 -174.64(8) . . . . ?
C35 C34 C39 C38 1.42(13) . . . . ?
N3 C34 C39 C38 -177.80(8) . . . . ?
C35 C34 C39 S2 177.49(7) . . . . ?
N3 C34 C39 S2 -1.72(12) . . . . ?
C28 S2 C39 C38 -146.34(8) . . . . ?
C28 S2 C39 C34 37.56(8) . . . . ?
C47 N4 C40 O4 175.59(10) . . . . ?
C54 N4 C40 O4 4.30(16) . . . . ?
C47 N4 C40 C41 -3.03(10) . . . . ?
C54 N4 C40 C41 -174.32(8) . . . . ?
O4 C40 C41 C42 2.09(18) . . . . ?
N4 C40 C41 C42 -179.35(10) . . . . ?
O4 C40 C41 C46 -176.21(10) . . . . ?
N4 C40 C41 C46 2.35(10) . . . . ?
C46 C41 C42 C43 0.85(15) . . . . ?
C40 C41 C42 C43 -177.25(10) . . . . ?
C41 C42 C43 C44 -0.25(15) . . . . ?
C42 C43 C44 C45 -0.32(16) . . . . ?
C43 C44 C45 C46 0.30(15) . . . . ?
C44 C45 C46 C41 0.30(14) . . . . ?
C44 C45 C46 C47 178.38(9) . . . . ?
C42 C41 C46 C45 -0.91(15) . . . . ?
C40 C41 C46 C45 177.58(9) . . . . ?
C42 C41 C46 C47 -179.36(9) . . . . ?
C40 C41 C46 C47 -0.88(10) . . . . ?
C40 N4 C47 O3 -176.98(9) . . . . ?
C54 N4 C47 O3 -5.45(15) . . . . ?
C40 N4 C47 C46 2.52(10) . . . . ?
C54 N4 C47 C46 174.05(8) . . . . ?
C45 C46 C47 O3 0.26(17) . . . . ?
C41 C46 C47 O3 178.55(10) . . . . ?
C45 C46 C47 N4 -179.20(10) . . . . ?
C41 C46 C47 N4 -0.92(10) . . . . ?
C34 N3 C48 C49 -138.82(8) . . . . ?
C33 N3 C48 C49 64.70(10) . . . . ?
N3 C48 C49 C50 64.41(10) . . . . ?
C48 C49 C50 C51 177.74(8) . . . . ?
C49 C50 C51 C52 -178.34(8) . . . . ?
C50 C51 C52 C53 71.55(11) . . . . ?
C51 C52 C53 C54 169.81(8) . . . . ?
C47 N4 C54 C53 84.41(12) . . . . ?
C40 N4 C54 C53 -105.20(11) . . . . ?
C52 C53 C54 N4 67.64(12) . . . . ?

_refine_diff_density_max         0.580
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.068

