# Supplementary Information (SI) for ChemComm.
# 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_CH_B1_0070
_database_code_depnum_ccdc_archive 'CCDC 2352883'
loop_
_audit_author_name
_audit_author_address
'Andrew Bond'
;University of Cambridge
United Kingdom
;
_audit_update_record             
;
2024-05-03 deposited with the CCDC.	2024-09-19 downloaded from the CCDC.
;
#===============================================================================
_audit_creation_method           SHELXL-2019/2

#-------------------------------------------------------------------------------
# Inserted by local software: cifUpdate ver. 3.1  (Andrew D. Bond, March 2019)
#-------------------------------------------------------------------------------
_cambridge_user_name             'Fergal Hanna'
_cambridge_user_crsid            feh27
_cambridge_supervisor_name       'Chris Hunter'
_cambridge_supervisor_crsid      ch664
_cambridge_crystallographer_name 'Andrew Bond'
_cambridge_crystallographer_crsid adb29
_cambridge_sample_id             FHBK4-62
_cambridge_data_id               CH_B1_0070

_database_code_CSD               ?
#-------------------------------------------------------------------------------

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H26 N4 O5 S'
_chemical_formula_sum            'C21 H26 N4 O5 S'
_chemical_formula_weight         446.52

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'

_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                   5.6438(2)
_cell_length_b                   35.5926(12)
_cell_length_c                   11.0653(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.787(2)
_cell_angle_gamma                90
_cell_volume                     2211.44(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      5.48
_cell_measurement_theta_max      66.54

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_F_000             944
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.644
_shelx_estimated_absorpt_T_min   0.694
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5926
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'

_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Incoatec I\mS Cu microsource'
_diffrn_measurement_device_type  'Bruker D8-QUEST PHOTON-III'
_diffrn_measurement_method       'ω and φ-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40491
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.482
_diffrn_reflns_theta_max         66.552
_diffrn_reflns_theta_full        66.552
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3896
_reflns_number_gt                3439
_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       'APEX4 (Bruker, 2021)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  SHELXL

_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)+(0.0379P)²+0.7977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3896
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0378
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0835
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.040

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 0.98727(6) 0.41977(2) 0.38839(4) 0.03242(12) Uani 1 1 d . . . . .
O1 O 0.45256(18) 0.30719(3) 0.25810(9) 0.0329(2) Uani 1 1 d . . . . .
O11 O 1.0731(2) 0.42091(3) 0.27079(11) 0.0421(3) Uani 1 1 d . . . . .
O12 O 1.1551(2) 0.42041(3) 0.49436(12) 0.0457(3) Uani 1 1 d . . . . .
O21 O 0.4342(3) 0.32089(4) 0.86087(11) 0.0613(4) Uani 1 1 d . . . . .
O22 O 0.1929(3) 0.29375(5) 0.72555(13) 0.0691(4) Uani 1 1 d . . . . .
N1 N 0.8260(2) 0.38182(3) 0.38516(13) 0.0323(3) Uani 1 1 d . . . . .
H1 H 0.790(3) 0.3733(5) 0.3132(18) 0.041(5) Uiso 1 1 d . . . . .
N2 N 0.3631(3) 0.31410(4) 0.75494(12) 0.0424(3) Uani 1 1 d . . . . .
N3 N 0.7430(2) 0.34078(3) 0.17158(11) 0.0299(3) Uani 1 1 d . . . . .
N4 N 0.9221(3) 0.21993(4) -0.09217(13) 0.0469(4) Uani 1 1 d . . . . .
C1 C 0.7115(3) 0.36556(4) 0.47912(13) 0.0289(3) Uani 1 1 d . . . . .
C2 C 0.8030(3) 0.36911(5) 0.60069(14) 0.0371(4) Uani 1 1 d . . . . .
H2A H 0.944364 0.383192 0.621069 0.044 Uiso 1 1 calc R U . . .
C3 C 0.6896(3) 0.35232(5) 0.69134(14) 0.0383(4) Uani 1 1 d . . . . .
H3A H 0.750195 0.354968 0.774154 0.046 Uiso 1 1 calc R U . . .
C4 C 0.4866(3) 0.33164(4) 0.65936(14) 0.0339(3) Uani 1 1 d . . . . .
C5 C 0.3931(3) 0.32748(4) 0.54010(14) 0.0315(3) Uani 1 1 d . . . . .
H5A H 0.252977 0.312968 0.521130 0.038 Uiso 1 1 calc R U . . .
C6 C 0.5034(2) 0.34449(4) 0.44768(13) 0.0274(3) Uani 1 1 d . . . . .
C7 C 0.3840(3) 0.34084(4) 0.32006(13) 0.0312(3) Uani 1 1 d . . . . .
H7A H 0.209200 0.340653 0.322910 0.037 Uiso 1 1 calc R U . . .
H7B H 0.424113 0.363111 0.272562 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6219(2) 0.30937(4) 0.18105(12) 0.0279(3) Uani 1 1 d . . . . .
C9 C 0.6583(3) 0.27693(4) 0.11412(13) 0.0318(3) Uani 1 1 d . . . . .
H9A H 0.565914 0.254924 0.122115 0.038 Uiso 1 1 calc R U . . .
C15 C 0.8333(3) 0.27814(4) 0.03627(13) 0.0323(3) Uani 1 1 d . . . . .
C16 C 0.9651(3) 0.31106(5) 0.02476(13) 0.0357(4) Uani 1 1 d . . . . .
H16A H 1.086733 0.312333 -0.028547 0.043 Uiso 1 1 calc R U . . .
C17 C 0.9119(3) 0.34127(4) 0.09325(14) 0.0343(3) Uani 1 1 d . . . . .
H17A H 0.998421 0.363885 0.085367 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8810(3) 0.24548(5) -0.03512(14) 0.0375(4) Uani 1 1 d . . . . .
C19 C 0.7873(3) 0.45759(4) 0.40163(14) 0.0334(3) Uani 1 1 d . . . . .
H19A H 0.692115 0.452362 0.470145 0.040 Uiso 1 1 calc R U . . .
H19B H 0.880803 0.480686 0.421706 0.040 Uiso 1 1 calc R U . . .
C20 C 0.6185(3) 0.46484(4) 0.28850(14) 0.0316(3) Uani 1 1 d . . . . .
H20A H 0.519044 0.442290 0.269499 0.038 Uiso 1 1 calc R U . . .
H20B H 0.711704 0.469657 0.218925 0.038 Uiso 1 1 calc R U . . .
C21 C 0.4582(3) 0.49849(4) 0.30623(14) 0.0337(3) Uani 1 1 d . . . . .
H21A H 0.365302 0.493425 0.375735 0.040 Uiso 1 1 calc R U . . .
H21B H 0.559013 0.520801 0.326758 0.040 Uiso 1 1 calc R U . . .
C22 C 0.2873(3) 0.50726(4) 0.19500(14) 0.0339(3) Uani 1 1 d . . . . .
H22A H 0.184420 0.485114 0.175418 0.041 Uiso 1 1 calc R U . . .
H22B H 0.380096 0.511835 0.125118 0.041 Uiso 1 1 calc R U . . .
C23 C 0.1303(3) 0.54133(4) 0.21192(15) 0.0360(3) Uani 1 1 d . . . . .
H23A H 0.045948 0.537429 0.285135 0.043 Uiso 1 1 calc R U . . .
H23B H 0.233146 0.563748 0.226359 0.043 Uiso 1 1 calc R U . . .
C24 C -0.0526(3) 0.54901(4) 0.10420(15) 0.0366(4) Uani 1 1 d . . . . .
H24A H 0.031904 0.552850 0.030996 0.044 Uiso 1 1 calc R U . . .
H24B H -0.155415 0.526595 0.089875 0.044 Uiso 1 1 calc R U . . .
C25 C -0.2094(3) 0.58298(5) 0.12045(16) 0.0421(4) Uani 1 1 d . . . . .
H25A H -0.288121 0.579798 0.195785 0.051 Uiso 1 1 calc R U . . .
H25B H -0.107838 0.605679 0.130272 0.051 Uiso 1 1 calc R U . . .
C26 C -0.3985(3) 0.58896(5) 0.01468(17) 0.0481(4) Uani 1 1 d . . . . .
H26A H -0.491223 0.611495 0.029269 0.072 Uiso 1 1 calc R U . . .
H26B H -0.504549 0.567096 0.006776 0.072 Uiso 1 1 calc R U . . .
H26C H -0.321985 0.592131 -0.060322 0.072 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 O12 1.4313(12) . ?
S1 O11 1.4342(12) . ?
S1 N1 1.6270(12) . ?
S1 C19 1.7721(15) . ?
O1 C8 1.3453(17) . ?
O1 C7 1.4518(17) . ?
O21 N2 1.2242(19) . ?
O22 N2 1.221(2) . ?
N1 C1 1.4034(19) . ?
N1 H1 0.86(2) . ?
N2 C4 1.4636(19) . ?
N3 C8 1.3201(18) . ?
N3 C17 1.3516(19) . ?
N4 C18 1.144(2) . ?
C1 C2 1.397(2) . ?
C1 C6 1.407(2) . ?
C2 C3 1.379(2) . ?
C2 H2A 0.9500 . ?
C3 C4 1.378(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.379(2) . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.508(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.398(2) . ?
C9 C15 1.375(2) . ?
C9 H9A 0.9500 . ?
C15 C16 1.401(2) . ?
C15 C18 1.446(2) . ?
C16 C17 1.366(2) . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9500 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.525(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.517(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.525(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.521(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.520(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.518(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?

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
O12 S1 O11 119.13(7) . . ?
O12 S1 N1 110.72(7) . . ?
O11 S1 N1 104.07(7) . . ?
O12 S1 C19 107.12(7) . . ?
O11 S1 C19 109.24(7) . . ?
N1 S1 C19 105.84(7) . . ?
C8 O1 C7 119.47(11) . . ?
C1 N1 S1 128.65(11) . . ?
C1 N1 H1 117.3(12) . . ?
S1 N1 H1 113.2(12) . . ?
O22 N2 O21 123.06(14) . . ?
O22 N2 C4 118.67(14) . . ?
O21 N2 C4 118.27(15) . . ?
C8 N3 C17 117.80(13) . . ?
C2 C1 N1 121.52(14) . . ?
C2 C1 C6 120.30(13) . . ?
N1 C1 C6 118.16(13) . . ?
C3 C2 C1 120.49(15) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 118.66(15) . . ?
C4 C3 H3A 120.7 . . ?
C2 C3 H3A 120.7 . . ?
C3 C4 C5 122.09(14) . . ?
C3 C4 N2 119.11(14) . . ?
C5 C4 N2 118.80(14) . . ?
C4 C5 C6 120.08(14) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C5 C6 C1 118.38(13) . . ?
C5 C6 C7 117.44(13) . . ?
C1 C6 C7 124.10(13) . . ?
O1 C7 C6 113.46(12) . . ?
O1 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
O1 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N3 C8 O1 120.38(13) . . ?
N3 C8 C9 123.51(13) . . ?
O1 C8 C9 116.10(13) . . ?
C15 C9 C8 117.35(14) . . ?
C15 C9 H9A 121.3 . . ?
C8 C9 H9A 121.3 . . ?
C9 C15 C16 120.32(14) . . ?
C9 C15 C18 120.13(14) . . ?
C16 C15 C18 119.54(14) . . ?
C17 C16 C15 117.35(14) . . ?
C17 C16 H16A 121.3 . . ?
C15 C16 H16A 121.3 . . ?
N3 C17 C16 123.66(14) . . ?
N3 C17 H17A 118.2 . . ?
C16 C17 H17A 118.2 . . ?
N4 C18 C15 178.85(19) . . ?
C20 C19 S1 114.41(10) . . ?
C20 C19 H19A 108.7 . . ?
S1 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
S1 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 C21 111.03(12) . . ?
C19 C20 H20A 109.4 . . ?
C21 C20 H20A 109.4 . . ?
C19 C20 H20B 109.4 . . ?
C21 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 113.19(12) . . ?
C22 C21 H21A 108.9 . . ?
C20 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C20 C21 H21B 108.9 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 C23 113.18(13) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.8 . . ?
C24 C23 C22 113.81(13) . . ?
C24 C23 H23A 108.8 . . ?
C22 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C25 C24 C23 114.05(13) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C26 C25 C24 113.14(15) . . ?
C26 C25 H25A 109.0 . . ?
C24 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?



