# Supplementary Information (SI) for Faraday Discussions.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_z501
_database_code_depnum_ccdc_archive 'CCDC 2352028'
loop_
_audit_author_name
_audit_author_address
'Brian Samas'
;Pfizer
United States of America
;
_audit_update_record             
;
2024-04-29 deposited with the CCDC.	2024-05-17 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_THETM01_z501                
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Data collection cut short because of time constraints on instrument.  Data 10 years old
;
_vrf_PLAT089_z501                
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       3.26 Note
RESPONSE: Data collection cut short because of time constraints on instrument.  Data 10 years old
;
# Added during the CSD deposition process: Monday 29 April 2024 04:47 PM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H27 N5 O4 S'
_chemical_formula_weight         457.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   9.1890(4)
_cell_length_b                   12.6757(6)
_cell_length_c                   10.9694(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 114.013(2)
_cell_angle_gamma                90.00
_cell_volume                     1167.10(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9919
_cell_measurement_theta_min      4.41
_cell_measurement_theta_max      44.59

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_absorpt_coefficient_mu    1.550
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8358
_exptl_absorpt_correction_T_max  0.9406
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15363
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_sigmaI/netI    0.0306
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.41
_diffrn_reflns_theta_max         44.59
_reflns_number_total             1846
_reflns_number_gt                1798
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0359P)²+0.0929P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.013(16)
_refine_ls_number_reflns         1846
_refine_ls_number_parameters     303
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0217
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0556
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
H4X H 0.938(2) 0.970(2) 0.222(2) 0.042(8) Uiso 1 1 d D . .
H3X H 0.535(4) 1.004(2) 0.171(3) 0.082(12) Uiso 1 1 d D . .
S1 S 0.31353(8) 0.99017(6) 0.29621(7) 0.0385(3) Uani 1 1 d . . .
N1 N 0.7270(3) 1.2594(2) -0.0658(3) 0.0444(7) Uani 1 1 d D . .
N2 N 0.5150(3) 1.2052(2) -0.0055(3) 0.0507(7) Uani 1 1 d . . .
N3 N 0.5843(3) 1.0544(2) 0.1344(2) 0.0367(6) Uani 1 1 d D . .
N4 N 0.8294(3) 0.96834(18) 0.2119(2) 0.0349(6) Uani 1 1 d D . .
N5 N 0.8357(3) 0.6853(2) 0.2984(2) 0.0414(7) Uani 1 1 d . . .
O1 O 0.8714(3) 0.59800(18) 0.1342(3) 0.0650(6) Uani 1 1 d . . .
O2 O 0.1594(2) 0.94155(16) 0.2588(2) 0.0566(6) Uani 1 1 d . . .
O3 O 0.3117(2) 1.10279(16) 0.28001(19) 0.0555(6) Uani 1 1 d . . .
O4 O 0.4028(2) 0.93681(15) 0.22910(17) 0.0392(5) Uani 1 1 d . . .
C1 C 0.8797(4) 1.2271(3) -0.0356(3) 0.0540(9) Uani 1 1 d . . .
H1 H 0.9483 1.2579 -0.0685 0.065 Uiso 1 1 calc R . .
C2 C 0.9171(4) 1.1437(2) 0.0489(3) 0.0489(9) Uani 1 1 d . . .
H2 H 1.0132 1.1073 0.0838 0.059 Uiso 1 1 calc R . .
C3 C 0.7798(3) 1.1235(2) 0.0730(3) 0.0334(7) Uani 1 1 d . . .
C4 C 0.6652(3) 1.1970(3) 0.0000(3) 0.0367(8) Uani 1 1 d . . .
C5 C 0.4823(4) 1.1320(3) 0.0624(3) 0.0500(9) Uani 1 1 d . . .
H5 H 0.3809 1.1324 0.0620 0.060 Uiso 1 1 calc R . .
C6 C 0.7353(4) 1.0468(2) 0.1428(3) 0.0312(7) Uani 1 1 d . . .
C7 C 0.7798(3) 0.8751(2) 0.2640(3) 0.0340(8) Uani 1 1 d . . .
H7 H 0.6671 0.8614 0.2084 0.041 Uiso 1 1 calc R . .
C8 C 0.8007(4) 0.8851(2) 0.4073(3) 0.0458(8) Uani 1 1 d . . .
H8A H 0.7363 0.9429 0.4159 0.055 Uiso 1 1 calc R . .
H8B H 0.9114 0.8999 0.4641 0.055 Uiso 1 1 calc R . .
C9 C 0.7499(4) 0.7825(3) 0.4499(3) 0.0592(10) Uani 1 1 d . . .
H9A H 0.6371 0.7715 0.3968 0.071 Uiso 1 1 calc R . .
H9B H 0.7654 0.7883 0.5426 0.071 Uiso 1 1 calc R . .
C10 C 0.8421(4) 0.6871(3) 0.4344(3) 0.0536(9) Uani 1 1 d . . .
H10 H 0.7877 0.6237 0.4455 0.064 Uiso 1 1 calc R . .
C11 C 1.0133(5) 0.6825(3) 0.5375(4) 0.0924(13) Uani 1 1 d . . .
H11A H 1.0634 0.6198 0.5239 0.139 Uiso 1 1 calc R . .
H11B H 1.0144 0.6813 0.6254 0.139 Uiso 1 1 calc R . .
H11C H 1.0701 0.7434 0.5284 0.139 Uiso 1 1 calc R . .
C12 C 0.8768(4) 0.7832(2) 0.2501(3) 0.0431(8) Uani 1 1 d . . .
H12A H 0.8582 0.7750 0.1570 0.052 Uiso 1 1 calc R . .
H12B H 0.9892 0.7979 0.3002 0.052 Uiso 1 1 calc R . .
C13 C 0.8351(3) 0.5971(3) 0.2298(4) 0.0459(8) Uani 1 1 d . . .
C14 C 0.7834(4) 0.4975(4) 0.2690(4) 0.0697(10) Uani 1 1 d . . .
H14 H 0.7368 0.4996 0.3300 0.084 Uiso 1 1 calc R . .
C15 C 0.8003(6) 0.4079(4) 0.2219(5) 0.1079(16) Uani 1 1 d . . .
H15A H 0.8466 0.4043 0.1607 0.129 Uiso 1 1 calc R . .
H15B H 0.7663 0.3466 0.2488 0.129 Uiso 1 1 calc R . .
C16 C 0.4126(4) 0.8649(3) 0.5167(4) 0.0512(9) Uani 1 1 d . . .
H16 H 0.3381 0.8165 0.4628 0.061 Uiso 1 1 calc R . .
C17 C 0.5103(5) 0.8381(3) 0.6454(4) 0.0620(10) Uani 1 1 d . . .
H17 H 0.5016 0.7714 0.6771 0.074 Uiso 1 1 calc R . .
C18 C 0.6200(5) 0.9076(4) 0.7279(4) 0.0642(10) Uani 1 1 d . . .
C19 C 0.7289(6) 0.8763(4) 0.8678(4) 0.1083(15) Uani 1 1 d . . .
H19A H 0.8212 0.9210 0.8992 0.162 Uiso 1 1 calc R . .
H19B H 0.7614 0.8042 0.8684 0.162 Uiso 1 1 calc R . .
H19C H 0.6737 0.8836 0.9251 0.162 Uiso 1 1 calc R . .
C20 C 0.6300(5) 1.0065(3) 0.6786(4) 0.0726(11) Uani 1 1 d . . .
H20 H 0.7036 1.0551 0.7331 0.087 Uiso 1 1 calc R . .
C21 C 0.5307(4) 1.0339(3) 0.5481(4) 0.0559(9) Uani 1 1 d . . .
H21 H 0.5373 1.1011 0.5166 0.067 Uiso 1 1 calc R . .
C22 C 0.4242(3) 0.9634(2) 0.4662(3) 0.0378(8) Uani 1 1 d . . .
H1X H 0.674(4) 1.319(2) -0.126(3) 0.072(11) Uiso 1 1 d D . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O3 1.438(2) . ?
S1 O2 1.4422(19) . ?
S1 O4 1.4713(19) . ?
S1 C22 1.756(3) . ?
N1 C4 1.343(4) . ?
N1 C1 1.367(4) . ?
N2 C5 1.299(4) . ?
N2 C4 1.361(4) . ?
N3 C6 1.356(3) . ?
N3 C5 1.366(4) . ?
N4 C6 1.333(3) . ?
N4 C7 1.464(4) . ?
N5 C13 1.347(4) . ?
N5 C12 1.458(4) . ?
N5 C10 1.469(4) . ?
O1 C13 1.223(4) . ?
C1 C2 1.354(4) . ?
C2 C3 1.414(4) . ?
C3 C4 1.390(4) . ?
C3 C6 1.398(4) . ?
C7 C8 1.510(4) . ?
C7 C12 1.512(4) . ?
C8 C9 1.519(4) . ?
C9 C10 1.525(4) . ?
C10 C11 1.520(5) . ?
C13 C14 1.474(5) . ?
C14 C15 1.283(5) . ?
C16 C17 1.372(5) . ?
C16 C22 1.388(4) . ?
C17 C18 1.367(5) . ?
C18 C20 1.383(5) . ?
C18 C19 1.505(5) . ?
C20 C21 1.393(5) . ?
C21 C22 1.359(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 S1 O2 115.38(11) . . ?
O3 S1 O4 112.04(11) . . ?
O2 S1 O4 110.12(12) . . ?
O3 S1 C22 107.19(13) . . ?
O2 S1 C22 107.29(13) . . ?
O4 S1 C22 104.04(11) . . ?
C4 N1 C1 108.0(2) . . ?
C5 N2 C4 112.8(2) . . ?
C6 N3 C5 122.3(3) . . ?
C6 N4 C7 126.3(2) . . ?
C13 N5 C12 116.5(2) . . ?
C13 N5 C10 124.7(3) . . ?
C12 N5 C10 116.6(3) . . ?
C2 C1 N1 110.4(3) . . ?
C1 C2 C3 105.8(3) . . ?
C4 C3 C6 117.4(3) . . ?
C4 C3 C2 107.1(3) . . ?
C6 C3 C2 135.3(3) . . ?
N1 C4 N2 125.1(3) . . ?
N1 C4 C3 108.6(2) . . ?
N2 C4 C3 126.4(3) . . ?
N2 C5 N3 125.5(3) . . ?
N4 C6 N3 120.1(3) . . ?
N4 C6 C3 124.4(3) . . ?
N3 C6 C3 115.6(3) . . ?
N4 C7 C8 114.2(2) . . ?
N4 C7 C12 107.0(2) . . ?
C8 C7 C12 109.9(2) . . ?
C7 C8 C9 108.9(2) . . ?
C8 C9 C10 113.0(2) . . ?
N5 C10 C11 110.9(3) . . ?
N5 C10 C9 109.3(3) . . ?
C11 C10 C9 113.7(3) . . ?
N5 C12 C7 111.6(2) . . ?
O1 C13 N5 122.0(3) . . ?
O1 C13 C14 119.4(3) . . ?
N5 C13 C14 118.5(3) . . ?
C15 C14 C13 122.3(4) . . ?
C17 C16 C22 120.6(3) . . ?
C18 C17 C16 121.3(3) . . ?
C17 C18 C20 118.2(3) . . ?
C17 C18 C19 120.7(4) . . ?
C20 C18 C19 121.0(4) . . ?
C18 C20 C21 120.6(4) . . ?
C22 C21 C20 120.6(3) . . ?
C21 C22 C16 118.7(3) . . ?
C21 C22 S1 121.6(3) . . ?
C16 C22 S1 119.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        44.59
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.106
_refine_diff_density_min         -0.098
_refine_diff_density_rms         0.024
