# 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_test1
_database_code_depnum_ccdc_archive 'CCDC 2110720'
loop_
_audit_author_name
_audit_author_address
'Konstantin Karaghiosoff'
;Ludwig Maximilian University
Germany
;
_audit_update_record             
;
2021-09-20 deposited with the CCDC.	2021-10-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
4-(1-(benzo[b]thiophen-5-yl)ethyl)morpholin-4-ium chloride
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H20 N O S, Cl'
_chemical_formula_sum            'C15 H20 Cl N O S'
_chemical_formula_weight         297.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

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

_cell_length_a                   7.2165(2)
_cell_length_b                   12.5371(4)
_cell_length_c                   16.4763(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1490.68(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6136
_cell_measurement_theta_min      2.0580
_cell_measurement_theta_max      31.3090

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    .
_exptl_crystal_density_diffrn    1.327
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.388
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.98522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_reflns_number            30202
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.041
_diffrn_reflns_theta_max         30.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4545
_reflns_number_gt                4002
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.756
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
;
'ORTEP (M. N. Burnett, C. K. Johnson, ORTEP-III: Oak Ridge Thermal Ellipsoid
# Plot Program for Crystal Structure Illustrations, Oak Ridge National
# Laboratory Report ORNL-6895, 1996). Windows version (L. J. Farrugia, Univ.
# Glasgow) used --- SCHAKAL (E. Keller, University of  Freiburg (Breisgau),
# Germany, 1995)'
;
_computing_publication_material  
;
PLATON (A. L. Spek, Acta Crystallogr, Sect. A, 1990, 46, C34, 1995 version).
# --- T.B.Cohen, Pure Appl. Chem. 1996,68,2339-2359 (atomic masses).
;
_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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0480P)²+0.0119P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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_abs_structure_details 
;
 Flack x determined using 1603 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4545
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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
S1 S -0.17298(9) 0.15662(5) 0.54512(4) 0.02510(14) Uani 1 1 d . . . . .
H1 H 0.201(4) 0.762(2) 0.6427(17) 0.025(7) Uiso 1 1 d . . . . .
Cl1 Cl 0.41885(7) 0.69928(5) 0.38987(4) 0.02404(13) Uani 1 1 d . . . . .
C1 C 0.4316(3) 0.80656(18) 0.59788(13) 0.0185(4) Uani 1 1 d . . . . .
H1A H 0.3936(8) 0.8029(2) 0.5424(12) 0.022 Uiso 1 1 calc R U . . .
H1B H 0.557(3) 0.7829(5) 0.60120(14) 0.022 Uiso 1 1 calc R U . . .
C5 C 0.2993(3) 0.62222(16) 0.61667(14) 0.0161(4) Uani 1 1 d . . . . .
H5 H 0.2399(17) 0.62472(17) 0.5653(15) 0.019 Uiso 1 1 calc R U . . .
C11 C -0.0799(3) 0.27926(17) 0.57240(13) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.0927(3) 0.45898(17) 0.63660(13) 0.0165(4) Uani 1 1 d . . . . .
O1 O 0.4674(3) 0.92944(14) 0.71127(10) 0.0251(4) Uani 1 1 d . . . . .
C4 C 0.3674(3) 0.74663(19) 0.73542(14) 0.0215(5) Uani 1 1 d . . . . .
H4A H 0.488(3) 0.7233(6) 0.7421(2) 0.026 Uiso 1 1 calc R U . . .
H4B H 0.2912(17) 0.7054(9) 0.7679(7) 0.026 Uiso 1 1 calc R U . . .
C9 C -0.0443(3) 0.46803(19) 0.57601(14) 0.0200(5) Uani 1 1 d . . . . .
H9 H -0.0767(11) 0.535(2) 0.5576(6) 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4890(3) 0.57205(19) 0.60433(15) 0.0231(5) Uani 1 1 d . . . . .
H6A H 0.5560(15) 0.6113(11) 0.5630(11) 0.035 Uiso 1 1 calc R U . . .
H6B H 0.4743(4) 0.4986(14) 0.5873(11) 0.035 Uiso 1 1 calc R U . . .
H6C H 0.5577(16) 0.5743(13) 0.6548(9) 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1741(3) 0.55847(17) 0.67404(13) 0.0181(4) Uani 1 1 d . . . . .
H7A H 0.2435(14) 0.5389(4) 0.7204(9) 0.022 Uiso 1 1 calc R U . . .
H7B H 0.076(2) 0.6030(9) 0.6915(4) 0.022 Uiso 1 1 calc R U . . .
C10 C -0.1311(3) 0.37969(19) 0.54362(14) 0.0205(4) Uani 1 1 d . . . . .
H10 H -0.225(3) 0.3872(3) 0.5021(13) 0.025 Uiso 1 1 calc R U . . .
C14 C 0.0833(3) 0.15699(19) 0.65435(14) 0.0207(4) Uani 1 1 d . . . . .
H14 H 0.174(3) 0.1322(8) 0.6953(12) 0.025 Uiso 1 1 calc R U . . .
N1 N 0.3109(3) 0.73597(14) 0.64846(11) 0.0148(3) Uani 1 1 d . . . . .
C13 C 0.1431(3) 0.35881(17) 0.66450(14) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.238(3) 0.3519(3) 0.7062(12) 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4175(4) 0.92029(18) 0.62779(14) 0.0237(5) Uani 1 1 d . . . . .
H2A H 0.4972(17) 0.9646(10) 0.5961(7) 0.028 Uiso 1 1 calc R U . . .
H2B H 0.294(3) 0.9450(6) 0.6206(2) 0.028 Uiso 1 1 calc R U . . .
C15 C -0.0305(3) 0.09088(19) 0.61261(15) 0.0234(5) Uani 1 1 d . . . . .
H15 H -0.0317(3) 0.019(2) 0.6195(3) 0.028 Uiso 1 1 calc R U . . .
C12 C 0.0574(3) 0.26723(18) 0.63276(13) 0.0170(4) Uani 1 1 d . . . . .
C3 C 0.3520(4) 0.8632(2) 0.75967(15) 0.0262(5) Uani 1 1 d . . . . .
H3A H 0.221(3) 0.8867(5) 0.75389(18) 0.031 Uiso 1 1 calc R U . . .
H3B H 0.3875(8) 0.8711(3) 0.8175(12) 0.031 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 C15 1.724(3) . ?
S1 C11 1.737(2) . ?
C1 N1 1.495(3) . ?
C1 C2 1.512(3) . ?
C1 H1A 0.96(2) . ?
C1 H1B 0.96(2) . ?
C5 C6 1.520(3) . ?
C5 N1 1.522(3) . ?
C5 C7 1.533(3) . ?
C5 H5 0.95(3) . ?
C11 C10 1.395(3) . ?
C11 C12 1.412(3) . ?
C8 C13 1.386(3) . ?
C8 C9 1.410(3) . ?
C8 C7 1.510(3) . ?
O1 C3 1.421(3) . ?
O1 C2 1.426(3) . ?
C4 N1 1.496(3) . ?
C4 C3 1.519(3) . ?
C4 H4A 0.92(2) . ?
C4 H4B 0.92(2) . ?
C9 C10 1.380(3) . ?
C9 H9 0.92(3) . ?
C6 H6A 0.969(17) . ?
C6 H6B 0.969(17) . ?
C6 H6C 0.969(17) . ?
C7 H7A 0.946(19) . ?
C7 H7B 0.946(19) . ?
C10 H10 0.97(3) . ?
C14 C15 1.354(3) . ?
C14 C12 1.439(3) . ?
C14 H14 0.99(3) . ?
N1 H1 0.86(3) . ?
C13 C12 1.405(3) . ?
C13 H13 0.97(3) . ?
C2 H2A 0.95(2) . ?
C2 H2B 0.95(2) . ?
C15 H15 0.91(3) . ?
C3 H3A 0.99(2) . ?
C3 H3B 0.99(2) . ?

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
C15 S1 C11 91.46(11) . . ?
N1 C1 C2 109.71(18) . . ?
N1 C1 H1A 109.7 . . ?
C2 C1 H1A 109.7 . . ?
N1 C1 H1B 109.7 . . ?
C2 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C6 C5 N1 112.60(18) . . ?
C6 C5 C7 113.44(19) . . ?
N1 C5 C7 108.00(17) . . ?
C6 C5 H5 107.5 . . ?
N1 C5 H5 107.5 . . ?
C7 C5 H5 107.5 . . ?
C10 C11 C12 121.4(2) . . ?
C10 C11 S1 127.46(18) . . ?
C12 C11 S1 111.05(16) . . ?
C13 C8 C9 119.5(2) . . ?
C13 C8 C7 120.7(2) . . ?
C9 C8 C7 119.70(19) . . ?
C3 O1 C2 110.28(18) . . ?
N1 C4 C3 108.5(2) . . ?
N1 C4 H4A 110.0 . . ?
C3 C4 H4A 110.0 . . ?
N1 C4 H4B 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C10 C9 C8 121.9(2) . . ?
C10 C9 H9 119.1 . . ?
C8 C9 H9 119.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C5 114.08(17) . . ?
C8 C7 H7A 108.7 . . ?
C5 C7 H7A 108.7 . . ?
C8 C7 H7B 108.7 . . ?
C5 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
C9 C10 C11 118.2(2) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C15 C14 C12 112.6(2) . . ?
C15 C14 H14 123.7 . . ?
C12 C14 H14 123.7 . . ?
C1 N1 C4 108.79(16) . . ?
C1 N1 C5 113.26(16) . . ?
C4 N1 C5 115.37(17) . . ?
C1 N1 H1 104.6(19) . . ?
C4 N1 H1 108.9(19) . . ?
C5 N1 H1 105.3(19) . . ?
C8 C13 C12 120.1(2) . . ?
C8 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
O1 C2 C1 111.91(19) . . ?
O1 C2 H2A 109.2 . . ?
C1 C2 H2A 109.2 . . ?
O1 C2 H2B 109.2 . . ?
C1 C2 H2B 109.2 . . ?
H2A C2 H2B 107.9 . . ?
C14 C15 S1 113.36(19) . . ?
C14 C15 H15 123.3 . . ?
S1 C15 H15 123.3 . . ?
C13 C12 C11 118.9(2) . . ?
C13 C12 C14 129.5(2) . . ?
C11 C12 C14 111.6(2) . . ?
O1 C3 C4 111.82(19) . . ?
O1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
O1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 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
C15 S1 C11 C10 -178.0(2) . . . . ?
C15 S1 C11 C12 -0.28(18) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C7 C8 C9 C10 -175.9(2) . . . . ?
C13 C8 C7 C5 113.6(2) . . . . ?
C9 C8 C7 C5 -70.3(3) . . . . ?
C6 C5 C7 C8 -75.6(3) . . . . ?
N1 C5 C7 C8 158.89(18) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
C12 C11 C10 C9 -0.3(3) . . . . ?
S1 C11 C10 C9 177.25(18) . . . . ?
C2 C1 N1 C4 -56.9(2) . . . . ?
C2 C1 N1 C5 173.38(18) . . . . ?
C3 C4 N1 C1 57.5(2) . . . . ?
C3 C4 N1 C5 -173.97(19) . . . . ?
C6 C5 N1 C1 53.4(2) . . . . ?
C7 C5 N1 C1 179.41(17) . . . . ?
C6 C5 N1 C4 -72.9(2) . . . . ?
C7 C5 N1 C4 53.1(2) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
C7 C8 C13 C12 175.8(2) . . . . ?
C3 O1 C2 C1 -58.2(3) . . . . ?
N1 C1 C2 O1 57.5(3) . . . . ?
C12 C14 C15 S1 0.4(3) . . . . ?
C11 S1 C15 C14 -0.07(19) . . . . ?
C8 C13 C12 C11 0.0(3) . . . . ?
C8 C13 C12 C14 -177.8(2) . . . . ?
C10 C11 C12 C13 0.3(3) . . . . ?
S1 C11 C12 C13 -177.60(16) . . . . ?
C10 C11 C12 C14 178.4(2) . . . . ?
S1 C11 C12 C14 0.5(2) . . . . ?
C15 C14 C12 C13 177.3(2) . . . . ?
C15 C14 C12 C11 -0.6(3) . . . . ?
C2 O1 C3 C4 59.6(3) . . . . ?
N1 C4 C3 O1 -59.7(3) . . . . ?

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.062

_shelxl_version_number           2014-3

