# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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. 
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data_cu_2023kb001_0m
_database_code_depnum_ccdc_archive 'CCDC 2262691'
loop_
_audit_author_name
_audit_author_address
'Kostas Bethanis'
;Agricultural University of Athens, Biotechnology Department
Greece
;

_audit_update_record             
;
2024-10-25 deposited with the CCDC.	2024-12-16 downloaded from the CCDC.
;
_publcif_datablock.id            {5504f69c-001d-4a34-ad44-2261e71722dc}
_audit_creation_date             2023-05-12
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            PropranololHCI
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H22 N O2, Cl'
_chemical_formula_sum            'C16 H22 Cl N O2'
_chemical_formula_weight         295.79
_chemical_melting_point          ?
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.7680(4)
_cell_length_b                   8.2450(2)
_cell_length_c                   13.9478(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.530(2)
_cell_angle_gamma                90
_cell_volume                     1565.80(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      4.2107
_cell_measurement_theta_max      68.1263
_cell_measurement_temperature    100.(2)
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.918
_exptl_absorpt_coefficient_mu    2.165
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9118
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0865 before and 0.0693 after correction.
The Ratio of minimum to maximum transmission is 0.9118.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            55147
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.289
_diffrn_reflns_theta_min         4.210
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker, D8-VENTURE'
_diffrn_measurement_method       ?
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2517
_reflns_number_total             2860
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2860
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0408
_refine_ls_R_factor_gt           0.0350
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+0.7922P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0835
_refine_ls_wR_factor_ref         0.0871
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C16-O1 \\sim C16-O1A
 with sigma of 0.02
3. Others
 Fixed Sof: H16(0.5) H16A(0.5) O1(0.5) H1C(0.5) O1A(0.5) H1AA(0.5)
4.a Ternary CH refined with riding coordinates:
 C16(H16), C16(H16A), C13(H13)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B)
4.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C6(H6), C9(H9), C10(H10), C1(H1), C3(H3), C2(H2)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
4.e Idealised tetrahedral OH refined as rotating group:
 O1(H1C), O1A(H1AA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

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
Cl Cl 0.71390(3) 0.89547(5) 0.65229(3) 0.04552(14) Uani 1 1 d . . . . .
C1' C 0.66658(12) 0.47588(18) 0.28857(11) 0.0293(3) Uani 1 1 d . . . . .
C2' C 0.74410(13) 0.55976(19) 0.26276(12) 0.0342(4) Uani 1 1 d . . . . .
H2' H 0.788988 0.613374 0.310739 0.041 Uiso 1 1 calc R U . . .
C3' C 0.75728(13) 0.5665(2) 0.16428(12) 0.0381(4) Uani 1 1 d . . . . .
H3' H 0.810714 0.626651 0.146574 0.046 Uiso 1 1 calc R U . . .
C4' C 0.69534(13) 0.4889(2) 0.09454(12) 0.0374(4) Uani 1 1 d . . . . .
H4' H 0.706216 0.493536 0.028910 0.045 Uiso 1 1 calc R U . . .
C5' C 0.61424(12) 0.40067(19) 0.11956(11) 0.0332(4) Uani 1 1 d . . . . .
C6' C 0.54876(14) 0.3158(2) 0.04960(13) 0.0452(4) Uani 1 1 d . . . . .
H6' H 0.558604 0.318144 -0.016376 0.054 Uiso 1 1 calc R U . . .
C7' C 0.47160(14) 0.2305(3) 0.07508(14) 0.0520(5) Uani 1 1 d . . . . .
H7' H 0.429039 0.172755 0.027060 0.062 Uiso 1 1 calc R U . . .
C8' C 0.45478(14) 0.2277(2) 0.17203(14) 0.0452(4) Uani 1 1 d . . . . .
H8' H 0.400092 0.169982 0.188983 0.054 Uiso 1 1 calc R U . . .
C9' C 0.51656(12) 0.30751(19) 0.24186(12) 0.0340(4) Uani 1 1 d . . . . .
H9' H 0.504766 0.304541 0.307244 0.041 Uiso 1 1 calc R U . . .
C10' C 0.59816(11) 0.39474(18) 0.21773(11) 0.0292(3) Uani 1 1 d . . . . .
O1 O 0.64702(8) 0.46116(13) 0.38192(7) 0.0316(3) Uani 1 1 d . . . . .
C1 C 0.71921(12) 0.52198(19) 0.45761(11) 0.0326(4) Uani 1 1 d . . . . .
H1A H 0.725623 0.640970 0.451421 0.039 Uiso 1 1 calc R U . . .
H1B H 0.783824 0.471811 0.453661 0.039 Uiso 1 1 calc R U . . .
C2 C 0.68609(12) 0.48018(19) 0.55366(11) 0.0330(4) Uani 1 1 d D . . . .
H2A H 0.743160 0.507761 0.604096 0.040 Uiso 0.5 1 calc R U P A 1
H2B H 0.621028 0.533353 0.555019 0.040 Uiso 0.5 1 calc R U P B 2
O3 O 0.61003(17) 0.5735(3) 0.57564(17) 0.0369(5) Uani 0.5 1 d D . P C 1
H11A H 0.631422 0.664984 0.595074 0.055 Uiso 0.5 1 calc R U P C 1
O2 O 0.74912(19) 0.5421(3) 0.62552(16) 0.0393(5) Uani 0.5 1 d D . P C 2
H1BB H 0.740343 0.642663 0.628406 0.059 Uiso 0.5 1 calc R U P C 2
C3 C 0.67209(13) 0.30012(19) 0.56283(11) 0.0351(4) Uani 1 1 d . . . . .
H3A H 0.619227 0.263740 0.511358 0.042 Uiso 1 1 calc R U . . .
H3B H 0.733348 0.243957 0.552840 0.042 Uiso 1 1 calc R U . . .
N N 0.64629(11) 0.25304(17) 0.65915(10) 0.0319(3) Uani 1 1 d . . . . .
HA H 0.6620(14) 0.143(3) 0.6701(13) 0.042(5) Uiso 1 1 d . . . . .
HB H 0.6842(15) 0.313(3) 0.7053(15) 0.048(6) Uiso 1 1 d . . . . .
C1'' C 0.53983(13) 0.2689(2) 0.67185(12) 0.0382(4) Uani 1 1 d . . . . .
H13 H 0.516967 0.381344 0.653412 0.046 Uiso 1 1 calc R U . . .
C2'' C 0.53251(15) 0.2417(2) 0.77784(13) 0.0473(5) Uani 1 1 d . . . . .
H14A H 0.556297 0.132625 0.796906 0.071 Uiso 1 1 calc R U . . .
H14B H 0.463871 0.252277 0.788000 0.071 Uiso 1 1 calc R U . . .
H14C H 0.572607 0.322427 0.817258 0.071 Uiso 1 1 calc R U . . .
C3'' C 0.47790(14) 0.1486(3) 0.60691(15) 0.0518(5) Uani 1 1 d . . . . .
H15A H 0.481676 0.173810 0.538901 0.078 Uiso 1 1 calc R U . . .
H15B H 0.409453 0.155761 0.618216 0.078 Uiso 1 1 calc R U . . .
H15C H 0.502564 0.038563 0.621690 0.078 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
C1' C2' 1.364(2) . ?
C1' O1 1.3736(18) . ?
C1' C10' 1.427(2) . ?
C2' C3' 1.413(2) . ?
C2' H2' 0.9500 . ?
C3' C4' 1.355(2) . ?
C3' H3' 0.9500 . ?
C4' C5' 1.419(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.412(2) . ?
C5' C10' 1.420(2) . ?
C6' C7' 1.364(3) . ?
C6' H6' 0.9500 . ?
C7' C8' 1.406(3) . ?
C7' H7' 0.9500 . ?
C8' C9' 1.363(2) . ?
C8' H8' 0.9500 . ?
C9' C10' 1.416(2) . ?
C9' H9' 0.9500 . ?
O1 C1 1.4292(18) . ?
C1 C2 1.517(2) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 O2 1.327(3) . ?
C2 O3 1.370(3) . ?
C2 C3 1.505(2) . ?
C2 H2A 1.0000 . ?
C2 H2B 1.0000 . ?
O3 H11A 0.8400 . ?
O2 H1BB 0.8400 . ?
C3 N 1.491(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
N C1'' 1.508(2) . ?
N HA 0.94(2) . ?
N HB 0.91(2) . ?
C1'' C2'' 1.514(2) . ?
C1'' C3'' 1.517(3) . ?
C1'' H13 1.0000 . ?
C2'' H14A 0.9800 . ?
C2'' H14B 0.9800 . ?
C2'' H14C 0.9800 . ?
C3'' H15A 0.9800 . ?
C3'' H15B 0.9800 . ?
C3'' H15C 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
C2' C1' O1 124.48(14) . . ?
C2' C1' C10' 121.13(14) . . ?
O1 C1' C10' 114.39(13) . . ?
C1' C2' C3' 119.64(16) . . ?
C1' C2' H2' 120.2 . . ?
C3' C2' H2' 120.2 . . ?
C4' C3' C2' 121.43(16) . . ?
C4' C3' H3' 119.3 . . ?
C2' C3' H3' 119.3 . . ?
C3' C4' C5' 119.99(15) . . ?
C3' C4' H4' 120.0 . . ?
C5' C4' H4' 120.0 . . ?
C6' C5' C4' 121.95(15) . . ?
C6' C5' C10' 118.32(15) . . ?
C4' C5' C10' 119.72(15) . . ?
C7' C6' C5' 121.16(17) . . ?
C7' C6' H6' 119.4 . . ?
C5' C6' H6' 119.4 . . ?
C6' C7' C8' 120.32(17) . . ?
C6' C7' H7' 119.8 . . ?
C8' C7' H7' 119.8 . . ?
C9' C8' C7' 120.33(17) . . ?
C9' C8' H8' 119.8 . . ?
C7' C8' H8' 119.8 . . ?
C8' C9' C10' 120.53(16) . . ?
C8' C9' H9' 119.7 . . ?
C10' C9' H9' 119.7 . . ?
C9' C10' C5' 119.31(15) . . ?
C9' C10' C1' 122.63(14) . . ?
C5' C10' C1' 118.06(14) . . ?
C1' O1 C1 117.17(12) . . ?
O1 C1 C2 107.78(13) . . ?
O1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
O2 C2 C3 113.13(16) . . ?
O3 C2 C3 115.03(16) . . ?
O2 C2 C1 109.33(17) . . ?
O3 C2 C1 114.19(16) . . ?
C3 C2 C1 110.99(13) . . ?
O3 C2 H2A 105.2 . . ?
C3 C2 H2A 105.2 . . ?
C1 C2 H2A 105.2 . . ?
O2 C2 H2B 107.7 . . ?
C3 C2 H2B 107.7 . . ?
C1 C2 H2B 107.7 . . ?
C2 O3 H11A 109.5 . . ?
C2 O2 H1BB 109.5 . . ?
N C3 C2 112.58(13) . . ?
N C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
N C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C3 N C1'' 116.66(13) . . ?
C3 N HA 108.6(11) . . ?
C1'' N HA 105.5(12) . . ?
C3 N HB 107.9(13) . . ?
C1'' N HB 109.6(12) . . ?
HA N HB 108.3(17) . . ?
N C1'' C2'' 107.97(14) . . ?
N C1'' C3'' 110.06(14) . . ?
C2'' C1'' C3'' 111.89(16) . . ?
N C1'' H13 109.0 . . ?
C2'' C1'' H13 109.0 . . ?
C3'' C1'' H13 109.0 . . ?
C1'' C2'' H14A 109.5 . . ?
C1'' C2'' H14B 109.5 . . ?
H14A C2'' H14B 109.5 . . ?
C1'' C2'' H14C 109.5 . . ?
H14A C2'' H14C 109.5 . . ?
H14B C2'' H14C 109.5 . . ?
C1'' C3'' H15A 109.5 . . ?
C1'' C3'' H15B 109.5 . . ?
H15A C3'' H15B 109.5 . . ?
C1'' C3'' H15C 109.5 . . ?
H15A C3'' H15C 109.5 . . ?
H15B C3'' H15C 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
O1 C1' C2' C3' 179.82(15) . . . . ?
C10' C1' C2' C3' -0.1(2) . . . . ?
C1' C2' C3' C4' -1.1(3) . . . . ?
C2' C3' C4' C5' 1.0(3) . . . . ?
C3' C4' C5' C6' -178.94(17) . . . . ?
C3' C4' C5' C10' 0.3(2) . . . . ?
C4' C5' C6' C7' 179.46(18) . . . . ?
C10' C5' C6' C7' 0.3(3) . . . . ?
C5' C6' C7' C8' 1.1(3) . . . . ?
C6' C7' C8' C9' -1.3(3) . . . . ?
C7' C8' C9' C10' 0.3(3) . . . . ?
C8' C9' C10' C5' 1.0(2) . . . . ?
C8' C9' C10' C1' -178.00(16) . . . . ?
C6' C5' C10' C9' -1.3(2) . . . . ?
C4' C5' C10' C9' 179.48(14) . . . . ?
C6' C5' C10' C1' 177.79(15) . . . . ?
C4' C5' C10' C1' -1.4(2) . . . . ?
C2' C1' C10' C9' -179.58(15) . . . . ?
O1 C1' C10' C9' 0.5(2) . . . . ?
C2' C1' C10' C5' 1.4(2) . . . . ?
O1 C1' C10' C5' -178.58(13) . . . . ?
C2' C1' O1 C1 -7.6(2) . . . . ?
C10' C1' O1 C1 172.33(13) . . . . ?
C1' O1 C1 C2 -175.34(12) . . . . ?
O1 C1 C2 O2 -176.92(15) . . . . ?
O1 C1 C2 O3 -74.40(19) . . . . ?
O1 C1 C2 C3 57.59(17) . . . . ?
O2 C2 C3 N 52.7(2) . . . . ?
O3 C2 C3 N -52.4(2) . . . . ?
C1 C2 C3 N 176.00(14) . . . . ?
C2 C3 N C1'' 82.40(18) . . . . ?
C3 N C1'' C2'' -171.02(14) . . . . ?
C3 N C1'' C3'' 66.58(18) . . . . ?

