# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_cyg380
_database_code_depnum_ccdc_archive 'CCDC 2062761'
_audit_update_record             
;
2021-02-12 deposited with the CCDC.	2021-05-17 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 N4 O5 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         436.44
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.3450(4)
_cell_length_b                   11.5313(8)
_cell_length_c                   23.7692(18)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2013.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2994
_cell_measurement_theta_min      2.4610
_cell_measurement_theta_max      27.0221
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904

_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Bruker X8APEX'
_diffrn_source_power             1.50
_diffrn_source_current           30.0
_diffrn_source_voltage           50

_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device       'APEX II CCD'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            12314
_diffrn_reflns_av_R_equivalents  0.0608
_diffrn_reflns_av_unetI/netI     0.0635
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       29

_refine_special_details          
;
;

_reflns_number_total             3942
_reflns_number_gt                3167
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0649
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_gt          0.0856
_refine_ls_wR_factor_ref         0.0945
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      0.998
_refine_ls_number_reflns         3942
_refine_ls_number_parameters     329
_refine_ls_number_restraints     371
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0325P)²+0.2860P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.302
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 1080 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(7)

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'

_computing_data_collection       'APEX3 (Ver 2019.11, Bruker AXS Inc., 2020)'
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'XT, VERSION 2018/2'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  'APEX3 (Ver 2019.11,Bruker AXS Inc., 2020)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.2729(12) 0.4620(9) 0.5437(3) 0.040(2) Uani d U P DG 0.629(15) A 1
H H1 0.343302 0.497275 0.57255 0.048 Uiso calc U P R 0.629(15) A 1
C C2 0.3425(12) 0.4531(8) 0.4895(3) 0.055(3) Uani d U P DG 0.629(15) A 1
H H2 0.460513 0.482182 0.481302 0.066 Uiso calc U P R 0.629(15) A 1
C C3 0.2394(16) 0.4015(7) 0.4473(2) 0.056(3) Uani d U P DG 0.629(15) A 1
H H3 0.287003 0.395347 0.410293 0.067 Uiso calc U P R 0.629(15) A 1
C C4 0.0667(16) 0.3589(6) 0.4594(2) 0.059(3) Uani d U P DG 0.629(15) A 1
H H4 -0.003719 0.323603 0.430532 0.071 Uiso calc U P R 0.629(15) A 1
C C5 -0.0029(13) 0.3678(8) 0.5136(3) 0.050(2) Uani d U P DG 0.629(15) A 1
H H5 -0.120932 0.338694 0.52178 0.06 Uiso calc U P R 0.629(15) A 1
C C6 0.1002(13) 0.4194(10) 0.5557(2) 0.034(2) Uani d U P DG 0.629(15) A 1
C C7 0.0141(17) 0.4309(13) 0.6143(4) 0.031(3) Uani d U P D 0.629(15) A 1
H H7 -0.112191 0.461717 0.609436 0.037 Uiso calc U P R 0.629(15) A 1
C C8 0.0015(12) 0.3145(16) 0.6455(7) 0.032(3) Uani d U P D 0.629(15) A 1
H H8A -0.077865 0.323921 0.678808 0.039 Uiso calc U P R 0.629(15) A 1
H H8B -0.055733 0.256438 0.620394 0.039 Uiso calc U P R 0.629(15) A 1
C C1A 0.331(2) 0.4760(17) 0.5523(5) 0.050(4) Uani d U P DG 0.371(15) A 2
H H1A 0.383041 0.510606 0.584881 0.06 Uiso calc U P R 0.371(15) A 2
C C2A 0.430(2) 0.4708(13) 0.5026(6) 0.057(4) Uani d U P DG 0.371(15) A 2
H H2A 0.550016 0.501785 0.501149 0.069 Uiso calc U P R 0.371(15) A 2
C C3A 0.354(3) 0.4202(10) 0.4550(5) 0.052(4) Uani d U P DG 0.371(15) A 2
H H3A 0.422018 0.416662 0.421013 0.062 Uiso calc U P R 0.371(15) A 2
C C4A 0.179(3) 0.3749(11) 0.4571(4) 0.053(4) Uani d U P DG 0.371(15) A 2
H H4A 0.127044 0.34036 0.424608 0.063 Uiso calc U P R 0.371(15) A 2
C C5A 0.080(2) 0.3802(14) 0.5069(5) 0.043(3) Uani d U P DG 0.371(15) A 2
H H5A -0.039934 0.34918 0.508339 0.051 Uiso calc U P R 0.371(15) A 2
C C6A 0.156(2) 0.4307(17) 0.5545(4) 0.034(3) Uani d U P DG 0.371(15) A 2
C C7A 0.040(3) 0.434(2) 0.6082(6) 0.034(5) Uani d U P D 0.371(15) A 2
H H7A -0.083678 0.462948 0.597845 0.04 Uiso calc U P R 0.371(15) A 2
C C8A 0.017(2) 0.311(3) 0.6333(11) 0.036(5) Uani d U P D 0.371(15) A 2
H H8A1 -0.087346 0.311669 0.659629 0.043 Uiso calc U P R 0.371(15) A 2
H H8A2 -0.010899 0.256057 0.602679 0.043 Uiso calc U P R 0.371(15) A 2
C C9 0.1832(5) 0.2703(3) 0.66405(17) 0.0351(10) Uani d . . D 1.0 . .
C C10 0.1145(5) 0.5106(3) 0.65356(15) 0.0271(8) Uani d . . D 1.0 . .
C C11 0.0551(5) 0.6331(3) 0.65964(16) 0.0282(9) Uani d . . . 1.0 . .
C C12 -0.0030(6) 0.6968(3) 0.61346(17) 0.0388(9) Uani d . . . 1.0 . .
H H12 -0.011803 0.661385 0.577474 0.047 Uiso calc U . R 1.0 . .
C C13 -0.0479(6) 0.8126(3) 0.62042(19) 0.0438(11) Uani d . . . 1.0 . .
H H13 -0.084787 0.858592 0.589288 0.053 Uiso calc U . R 1.0 . .
C C14 -0.0378(5) 0.8591(3) 0.6735(2) 0.0439(11) Uani d . . . 1.0 . .
H H14 -0.068437 0.938592 0.677904 0.053 Uiso calc U . R 1.0 . .
C C15 0.0585(5) 0.6886(3) 0.71143(17) 0.0346(10) Uani d . . . 1.0 . .
H H15 0.095886 0.644955 0.743293 0.041 Uiso calc U . R 1.0 . .
C C16 0.5122(5) 0.3346(3) 0.77281(14) 0.0268(8) Uani d . . . 1.0 . .
C C17 0.4655(5) 0.2304(3) 0.79790(18) 0.0343(9) Uani d . . . 1.0 . .
H H17 0.429364 0.166022 0.775604 0.041 Uiso calc U . R 1.0 . .
C C18 0.4723(6) 0.2214(3) 0.85557(18) 0.0413(10) Uani d . . . 1.0 . .
H H18 0.439927 0.15102 0.873803 0.05 Uiso calc U . R 1.0 . .
C C19 0.5272(6) 0.3168(4) 0.88650(17) 0.0402(10) Uani d . . . 1.0 . .
C C20 0.5715(6) 0.4211(4) 0.86205(19) 0.0438(11) Uani d . . . 1.0 . .
H H20 0.606841 0.485448 0.884479 0.053 Uiso calc U . R 1.0 . .
C C21 0.5636(5) 0.4303(3) 0.80431(18) 0.0368(10) Uani d . . . 1.0 . .
H H21 0.593012 0.501384 0.786294 0.044 Uiso calc U . R 1.0 . .
N N1 0.3048(4) 0.3617(3) 0.67695(13) 0.0278(7) Uani d . . . 1.0 . .
N N2 0.2470(4) 0.4783(3) 0.68494(13) 0.0268(7) Uani d . . . 1.0 . .
N N3 0.0124(5) 0.8000(3) 0.71941(15) 0.0425(9) Uani d . . . 1.0 . .
N N4 0.5397(6) 0.3061(4) 0.94814(18) 0.0588(11) Uani d . . . 1.0 . .
O O1 0.2206(4) 0.1701(2) 0.67139(14) 0.0490(8) Uani d . . . 1.0 . .
O O2 0.5801(4) 0.2345(2) 0.67716(12) 0.0372(7) Uani d . . . 1.0 . .
O O3 0.6148(3) 0.4470(2) 0.68346(11) 0.0361(7) Uani d . . . 1.0 . .
O O4 0.6226(6) 0.3826(4) 0.97365(16) 0.0803(13) Uani d . . . 1.0 . .
O O5 0.4703(7) 0.2220(4) 0.96995(16) 0.1033(16) Uani d . . . 1.0 . .
S S1 0.52165(12) 0.34315(8) 0.69884(4) 0.0286(2) Uani d . . . 1.0 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.39 ?
C1 C6 . 1.39 ?
C2 C3 . 1.39 ?
C3 C4 . 1.39 ?
C4 C5 . 1.39 ?
C5 C6 . 1.39 ?
C6 C7 . 1.533(7) ?
C7 C10 . 1.503(7) ?
C7 C8 . 1.537(8) ?
C8 C9 . 1.495(8) ?
C1A C2A . 1.39 ?
C1A C6A . 1.39 ?
C2A C3A . 1.39 ?
C3A C4A . 1.39 ?
C4A C5A . 1.39 ?
C5A C6A . 1.39 ?
C6A C7A . 1.534(10) ?
C7A C10 . 1.501(9) ?
C7A C8A . 1.541(11) ?
C8A C9 . 1.497(10) ?
C9 O1 . 1.201(5) ?
C9 N1 . 1.415(5) ?
C10 N2 . 1.281(5) ?
C10 C11 . 1.486(5) ?
C11 C12 . 1.388(5) ?
C11 C15 . 1.388(5) ?
C12 C13 . 1.385(5) ?
C13 C14 . 1.372(6) ?
C14 N3 . 1.338(5) ?
C15 N3 . 1.342(5) ?
C16 C21 . 1.385(5) ?
C16 C17 . 1.385(5) ?
C16 S1 . 1.762(3) ?
C17 C18 . 1.376(6) ?
C18 C19 . 1.384(6) ?
C19 C20 . 1.374(6) ?
C19 N4 . 1.473(6) ?
C20 C21 . 1.378(6) ?
N1 N2 . 1.423(4) ?
N1 S1 . 1.689(3) ?
N4 O5 . 1.212(5) ?
N4 O4 . 1.231(5) ?
O2 S1 . 1.422(3) ?
O3 S1 . 1.427(3) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 120.0 ?
C1 C2 C3 . . 120.0 ?
C4 C3 C2 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C6 C5 C4 . . 120.0 ?
C5 C6 C1 . . 120.0 ?
C5 C6 C7 . . 117.8(5) ?
C1 C6 C7 . . 122.1(5) ?
C10 C7 C6 . . 114.5(6) ?
C10 C7 C8 . . 105.3(13) ?
C6 C7 C8 . . 112.8(8) ?
C9 C8 C7 . . 112.7(12) ?
C2A C1A C6A . . 120.0 ?
C1A C2A C3A . . 120.0 ?
C4A C3A C2A . . 120.0 ?
C3A C4A C5A . . 120.0 ?
C4A C5A C6A . . 120.0 ?
C5A C6A C1A . . 120.0 ?
C5A C6A C7A . . 117.6(7) ?
C1A C6A C7A . . 122.4(7) ?
C10 C7A C6A . . 114.1(9) ?
C10 C7A C8A . . 108.(2) ?
C6A C7A C8A . . 111.3(12) ?
C9 C8A C7A . . 113.(2) ?
O1 C9 N1 . . 122.7(4) ?
O1 C9 C8 . . 125.1(8) ?
N1 C9 C8 . . 111.9(8) ?
O1 C9 C8A . . 124.1(15) ?
N1 C9 C8A . . 112.6(14) ?
N2 C10 C11 . . 116.3(3) ?
N2 C10 C7A . . 121.6(12) ?
C11 C10 C7A . . 121.7(12) ?
N2 C10 C7 . . 123.8(8) ?
C11 C10 C7 . . 119.8(8) ?
C12 C11 C15 . . 117.6(3) ?
C12 C11 C10 . . 121.1(3) ?
C15 C11 C10 . . 121.3(3) ?
C13 C12 C11 . . 119.3(4) ?
C14 C13 C12 . . 118.3(4) ?
N3 C14 C13 . . 124.5(4) ?
N3 C15 C11 . . 124.2(4) ?
C21 C16 C17 . . 121.7(4) ?
C21 C16 S1 . . 118.9(3) ?
C17 C16 S1 . . 119.2(3) ?
C18 C17 C16 . . 119.1(4) ?
C17 C18 C19 . . 118.7(4) ?
C20 C19 C18 . . 122.7(4) ?
C20 C19 N4 . . 118.6(4) ?
C18 C19 N4 . . 118.7(4) ?
C19 C20 C21 . . 118.6(4) ?
C20 C21 C16 . . 119.2(4) ?
C9 N1 N2 . . 123.0(3) ?
C9 N1 S1 . . 124.6(2) ?
N2 N1 S1 . . 111.1(2) ?
C10 N2 N1 . . 115.1(3) ?
C14 N3 C15 . . 116.2(3) ?
O5 N4 O4 . . 124.8(5) ?
O5 N4 C19 . . 117.8(5) ?
O4 N4 C19 . . 117.4(4) ?
O2 S1 O3 . . 120.15(15) ?
O2 S1 N1 . . 106.55(16) ?
O3 S1 N1 . . 105.49(16) ?
O2 S1 C16 . . 108.92(17) ?
O3 S1 C16 . . 108.74(17) ?
N1 S1 C16 . . 106.10(16) ?



