# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2206744'
loop_
_audit_author_name
_audit_author_address
'Dieter Schollmeyer'
;University of Mainz Department of Chemistry
Germany
;
_audit_update_record             
;
2022-09-12 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
"(E)-3-(3'-bromo-4'-hydroxyphenyl)-2-(hydroxyimino)-N-(2''-thiocyanatoethyl)proppanamide ethyl acetate"
_chemical_name_common            'Psammaplin B'
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Br N3 O3 S, C4 H8 O2'
_chemical_formula_sum            'C16 H20 Br N3 O5 S'
_chemical_formula_weight         446.32

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'
Br Br -0.2901 2.4595 '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                   19.9760(12)
_cell_length_b                   6.7233(3)
_cell_length_c                   14.7489(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.337(5)
_cell_angle_gamma                90
_cell_volume                     1948.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13589
_cell_measurement_theta_min      2.70
_cell_measurement_theta_max      28.31

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.570
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.248
_shelx_estimated_absorpt_T_min   0.361
_shelx_estimated_absorpt_T_max   0.936
_exptl_absorpt_correction_type   integration
_exptl_absorpt_correction_T_min  0.5126
_exptl_absorpt_correction_T_max  0.8995
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_detector_area_resol_mean 6.67
_diffrn_reflns_number            9405
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.813
_diffrn_reflns_theta_max         28.017
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4610
_reflns_number_gt                3789
_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       'X-Area WinXpose 2.0.22.0 (STOE, 2016)'
_computing_cell_refinement       'X-Area Recipe 1.36.0.0 (STOE, 2020)'
_computing_data_reduction        'X-Area Integrate 1.77.0.0 (STOE, 2019)'
_computing_structure_solution    'SHELXT-2014 (Shelxdrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0217P)²+4.7807P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     Dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4610
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.0966
_refine_ls_wR_factor_gt          0.0869
_refine_ls_goodness_of_fit_ref   1.134
_refine_ls_restrained_S_all      1.134
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.57491(17) 0.8306(5) 0.6390(3) 0.0442(8) Uani 1 1 d . . . . .
C2 C 0.60525(17) 0.6886(5) 0.6611(2) 0.0294(7) Uani 1 1 d . . . . .
S3 S 0.64907(4) 0.47819(12) 0.69310(6) 0.02713(17) Uani 1 1 d . . . . .
C4 C 0.57551(17) 0.3158(5) 0.6943(2) 0.0259(6) Uani 1 1 d . . . . .
H4A H 0.5958(19) 0.198(6) 0.714(2) 0.033(7) Uiso 1 1 d . U . . .
H4B H 0.5496(19) 0.364(6) 0.736(3) 0.033(7) Uiso 1 1 d . U . . .
C5 C 0.53352(17) 0.2960(5) 0.5983(2) 0.0277(7) Uani 1 1 d . . . . .
H5A H 0.5167(19) 0.425(6) 0.577(3) 0.034(7) Uiso 1 1 d . U . . .
H5B H 0.5610(19) 0.251(6) 0.556(3) 0.034(7) Uiso 1 1 d . U . . .
N6 N 0.47634(14) 0.1630(4) 0.59747(19) 0.0253(5) Uani 1 1 d . . . . .
H6 H 0.484(2) 0.048(6) 0.602(3) 0.035(11) Uiso 1 1 d . . . . .
C7 C 0.41192(16) 0.2261(5) 0.5842(2) 0.0236(6) Uani 1 1 d . . . . .
O8 O 0.39587(13) 0.4035(3) 0.57851(18) 0.0363(6) Uani 1 1 d . . . . .
C9 C 0.35782(15) 0.0674(5) 0.57676(19) 0.0216(6) Uani 1 1 d . . . . .
N10 N 0.37972(13) -0.1118(4) 0.57602(17) 0.0213(5) Uani 1 1 d . . . . .
O11 O 0.32734(12) -0.2511(4) 0.56738(16) 0.0267(5) Uani 1 1 d . . . . .
H11 H 0.348(3) -0.358(8) 0.569(3) 0.069(17) Uiso 1 1 d . . . . .
C12 C 0.28514(16) 0.1323(5) 0.5697(2) 0.0249(6) Uani 1 1 d . . . . .
H12A H 0.2836(19) 0.239(6) 0.606(3) 0.033(10) Uiso 1 1 d . . . . .
H12B H 0.2607(17) 0.024(5) 0.593(2) 0.023(9) Uiso 1 1 d . . . . .
C13 C 0.25146(15) 0.1808(5) 0.4712(2) 0.0232(6) Uani 1 1 d . . . . .
C14 C 0.25806(15) 0.0506(5) 0.3995(2) 0.0230(6) Uani 1 1 d . . . . .
H14 H 0.2819(16) -0.076(5) 0.414(2) 0.021(8) Uiso 1 1 d . . . . .
C15 C 0.22704(15) 0.0948(5) 0.3098(2) 0.0230(6) Uani 1 1 d . . . . .
Br16 Br 0.23843(2) -0.08463(5) 0.21417(2) 0.02936(10) Uani 1 1 d . . . . .
C17 C 0.18932(15) 0.2687(5) 0.2889(2) 0.0241(6) Uani 1 1 d . . . . .
O18 O 0.15945(12) 0.3032(4) 0.19895(16) 0.0311(5) Uani 1 1 d . . . . .
H18 H 0.143(2) 0.410(7) 0.200(3) 0.047 Uiso 1 1 d . U . . .
C19 C 0.18351(17) 0.3980(5) 0.3603(2) 0.0290(7) Uani 1 1 d . . . . .
H19 H 0.1600(19) 0.514(6) 0.345(3) 0.034(10) Uiso 1 1 d . . . . .
C20 C 0.21462(17) 0.3550(5) 0.4501(2) 0.0280(7) Uani 1 1 d . . . . .
H20 H 0.2115(19) 0.440(6) 0.498(3) 0.039(11) Uiso 1 1 d . . . . .
C1A C 0.0242(2) 0.9544(6) 0.1528(3) 0.0428(9) Uani 1 1 d . . . . .
H1AA H 0.057949 1.061043 0.166680 0.075(9) Uiso 1 1 calc R U . . .
H1AB H 0.002123 0.932539 0.206112 0.075(9) Uiso 1 1 calc R U . . .
H1AC H -0.010044 0.992148 0.099366 0.075(9) Uiso 1 1 calc R U . . .
C2A C 0.05894(17) 0.7668(5) 0.1316(2) 0.0310(7) Uani 1 1 d . . . . .
O3A O 0.07982(13) 0.6407(4) 0.18787(17) 0.0372(6) Uani 1 1 d . . . . .
O4A O 0.06259(14) 0.7530(4) 0.04285(16) 0.0407(6) Uani 1 1 d . . . . .
C5A C 0.0946(2) 0.5739(6) 0.0141(3) 0.0412(9) Uani 1 1 d . . . . .
H5AA H 0.074281 0.453768 0.036942 0.052(9) Uiso 1 1 calc R U . . .
H5AB H 0.144004 0.574561 0.039395 0.052(9) Uiso 1 1 calc R U . . .
C6A C 0.0830(2) 0.5738(6) -0.0885(3) 0.0402(8) Uani 1 1 d . . . . .
H6AA H 0.101481 0.451214 -0.110165 0.052(7) Uiso 1 1 calc R U . . .
H6AB H 0.105758 0.688904 -0.110100 0.052(7) Uiso 1 1 calc R U . . .
H6AC H 0.034031 0.581039 -0.112629 0.052(7) 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
N1 C2 1.146(4) . ?
C2 S3 1.686(3) . ?
S3 C4 1.833(3) . ?
C4 C5 1.516(4) . ?
C4 H4A 0.91(4) . ?
C4 H4B 0.93(4) . ?
C5 N6 1.449(4) . ?
C5 H5A 0.96(4) . ?
C5 H5B 0.94(4) . ?
N6 C7 1.336(4) . ?
N6 H6 0.79(4) . ?
C7 O8 1.234(4) . ?
C7 C9 1.509(4) . ?
C9 N10 1.283(4) . ?
C9 C12 1.502(4) . ?
N10 O11 1.393(3) . ?
O11 H11 0.82(5) . ?
C12 C13 1.523(4) . ?
C12 H12A 0.90(4) . ?
C12 H12B 0.97(4) . ?
C13 C20 1.388(4) . ?
C13 C14 1.396(4) . ?
C14 C15 1.390(4) . ?
C14 H14 0.98(3) . ?
C15 C17 1.395(4) . ?
C15 Br16 1.900(3) . ?
C17 O18 1.373(4) . ?
C17 C19 1.387(5) . ?
O18 H18 0.79(4) . ?
C19 C20 1.388(5) . ?
C19 H19 0.92(4) . ?
C20 H20 0.92(4) . ?
C1A C2A 1.499(5) . ?
C1A H1AA 0.9800 . ?
C1A H1AB 0.9800 . ?
C1A H1AC 0.9800 . ?
C2A O3A 1.207(4) . ?
C2A O4A 1.327(4) . ?
O4A C5A 1.461(4) . ?
C5A C6A 1.489(5) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 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
N1 C2 S3 179.3(4) . . ?
C2 S3 C4 97.22(16) . . ?
C5 C4 S3 110.7(2) . . ?
C5 C4 H4A 111(2) . . ?
S3 C4 H4A 102(2) . . ?
C5 C4 H4B 112(2) . . ?
S3 C4 H4B 110(2) . . ?
H4A C4 H4B 111(3) . . ?
N6 C5 C4 111.4(3) . . ?
N6 C5 H5A 109(2) . . ?
C4 C5 H5A 109(2) . . ?
N6 C5 H5B 110(2) . . ?
C4 C5 H5B 110(2) . . ?
H5A C5 H5B 106(3) . . ?
C7 N6 C5 122.9(3) . . ?
C7 N6 H6 119(3) . . ?
C5 N6 H6 118(3) . . ?
O8 C7 N6 123.3(3) . . ?
O8 C7 C9 120.3(3) . . ?
N6 C7 C9 116.4(3) . . ?
N10 C9 C12 126.8(3) . . ?
N10 C9 C7 115.1(3) . . ?
C12 C9 C7 118.1(3) . . ?
C9 N10 O11 112.4(2) . . ?
N10 O11 H11 103(4) . . ?
C9 C12 C13 112.6(2) . . ?
C9 C12 H12A 109(2) . . ?
C13 C12 H12A 110(2) . . ?
C9 C12 H12B 107(2) . . ?
C13 C12 H12B 109.8(19) . . ?
H12A C12 H12B 108(3) . . ?
C20 C13 C14 118.5(3) . . ?
C20 C13 C12 121.3(3) . . ?
C14 C13 C12 120.1(3) . . ?
C15 C14 C13 120.0(3) . . ?
C15 C14 H14 120.8(19) . . ?
C13 C14 H14 119.0(19) . . ?
C14 C15 C17 121.3(3) . . ?
C14 C15 Br16 118.6(2) . . ?
C17 C15 Br16 120.0(2) . . ?
O18 C17 C19 123.2(3) . . ?
O18 C17 C15 118.6(3) . . ?
C19 C17 C15 118.2(3) . . ?
C17 O18 H18 104(3) . . ?
C17 C19 C20 120.7(3) . . ?
C17 C19 H19 117(2) . . ?
C20 C19 H19 122(2) . . ?
C13 C20 C19 121.2(3) . . ?
C13 C20 H20 117(2) . . ?
C19 C20 H20 121(2) . . ?
C2A C1A H1AA 109.5 . . ?
C2A C1A H1AB 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
C2A C1A H1AC 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
O3A C2A O4A 123.7(3) . . ?
O3A C2A C1A 124.3(3) . . ?
O4A C2A C1A 111.9(3) . . ?
C2A O4A C5A 116.6(3) . . ?
O4A C5A C6A 107.4(3) . . ?
O4A C5A H5AA 110.2 . . ?
C6A C5A H5AA 110.2 . . ?
O4A C5A H5AB 110.2 . . ?
C6A C5A H5AB 110.2 . . ?
H5AA C5A H5AB 108.5 . . ?
C5A C6A H6AA 109.5 . . ?
C5A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
C5A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?

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
C2 S3 C4 C5 64.2(3) . . . . ?
S3 C4 C5 N6 178.2(2) . . . . ?
C4 C5 N6 C7 110.0(3) . . . . ?
C5 N6 C7 O8 -5.6(5) . . . . ?
C5 N6 C7 C9 174.7(3) . . . . ?
O8 C7 C9 N10 174.5(3) . . . . ?
N6 C7 C9 N10 -5.8(4) . . . . ?
O8 C7 C9 C12 -4.7(4) . . . . ?
N6 C7 C9 C12 175.1(3) . . . . ?
C12 C9 N10 O11 0.1(4) . . . . ?
C7 C9 N10 O11 -178.9(2) . . . . ?
N10 C9 C12 C13 -94.3(4) . . . . ?
C7 C9 C12 C13 84.7(3) . . . . ?
C9 C12 C13 C20 -132.0(3) . . . . ?
C9 C12 C13 C14 47.0(4) . . . . ?
C20 C13 C14 C15 -1.2(5) . . . . ?
C12 C13 C14 C15 179.7(3) . . . . ?
C13 C14 C15 C17 0.4(5) . . . . ?
C13 C14 C15 Br16 179.1(2) . . . . ?
C14 C15 C17 O18 -179.5(3) . . . . ?
Br16 C15 C17 O18 1.8(4) . . . . ?
C14 C15 C17 C19 0.1(5) . . . . ?
Br16 C15 C17 C19 -178.5(2) . . . . ?
O18 C17 C19 C20 179.7(3) . . . . ?
C15 C17 C19 C20 0.1(5) . . . . ?
C14 C13 C20 C19 1.5(5) . . . . ?
C12 C13 C20 C19 -179.5(3) . . . . ?
C17 C19 C20 C13 -0.9(5) . . . . ?
O3A C2A O4A C5A -0.6(5) . . . . ?
C1A C2A O4A C5A -179.1(3) . . . . ?
C2A O4A C5A C6A 170.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C4 H4A N1 0.91(4) 2.71(4) 3.362(5) 129(3) 1_545 yes
C5 H5B N10 0.94(4) 2.63(4) 3.570(4) 171(3) 3_656 yes
N6 H6 N1 0.79(4) 2.32(4) 2.969(4) 140(4) 1_545 yes
O11 H11 O8 0.82(5) 1.86(5) 2.686(3) 177(5) 1_545 yes
C12 H12A Br16 0.90(4) 3.05(4) 3.921(3) 165(3) 4_566 yes
C14 H14 O11 0.98(3) 2.57(3) 3.306(4) 132(2) . yes
O18 H18 O3A 0.79(4) 1.99(5) 2.759(3) 165(4) . yes
C1A H1AA O18 0.98 2.58 3.550(5) 171.6 1_565 yes

_refine_diff_density_max         0.646
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.087


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: EtOAc/Penthan'
