# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_schm159
_database_code_depnum_ccdc_archive 'CCDC 2291748'
loop_
_audit_author_name
_audit_author_address
'Martin Nieger'
;University of Helsinki
Finland
;
_audit_update_record             
;
2023-08-30 deposited with the CCDC.	2024-03-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
;
1-(2,5-dihydroxyphenyl)-4-ethylpyridin-1-ium chloride water solvate
;

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N O2, Cl, H2 O'
_chemical_formula_sum            'C13 H16 Cl N O3'
_chemical_formula_weight         269.72

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'
Cl Cl 0.1484 0.1585 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   11.9361(3)
_cell_length_b                   7.3938(2)
_cell_length_c                   14.4601(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.592(1)
_cell_angle_gamma                90
_cell_volume                     1273.64(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       blocks
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.300
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_T_max  0.9582
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2014)'
_exptl_absorpt_special_details   ?

_exptl_special_details           
;
 dx = 40 mm, 1 deg., 4+1 runs, 764 frames, 12 sec./frame
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'INCOATEC microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE with PhotonII CPAD detector'
_diffrn_measurement_method       'rotation in φ and ω, 1°, shutterless'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31472
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.148
_diffrn_reflns_theta_max         27.579
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2944
_reflns_number_gt                2801
_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       'APEX3 (Bruker AXS Inc., 2019)'
_computing_cell_refinement       'APEX3 (Bruker AXS Inc., 2019)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'publCIF (Westrip, 2010)'

_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)+(0.0411P)²+0.4386P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2944
_refine_ls_number_parameters     175
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_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
Cl1 Cl 0.19866(2) 0.61923(4) 0.04035(2) 0.02514(10) Uani 1 1 d . . . . .
N1 N 0.78934(7) 0.56721(11) 0.26148(5) 0.01361(17) Uani 1 1 d . . . . .
C2 C 0.85552(8) 0.50638(13) 0.19512(6) 0.01613(19) Uani 1 1 d . . . . .
H2 H 0.8224 0.4659 0.1374 0.019 Uiso 1 1 calc R U . . .
C3 C 0.96977(8) 0.50307(14) 0.21095(7) 0.0182(2) Uani 1 1 d . . . . .
H3 H 1.0152 0.4600 0.1640 0.022 Uiso 1 1 calc R U . . .
C4 C 1.02056(8) 0.56230(14) 0.29536(7) 0.0166(2) Uani 1 1 d . . . . .
C5 C 0.95049(8) 0.62683(13) 0.36169(7) 0.0170(2) Uani 1 1 d . . . . .
H5 H 0.9820 0.6697 0.4195 0.020 Uiso 1 1 calc R U . . .
C6 C 0.83581(8) 0.62854(13) 0.34358(7) 0.01588(19) Uani 1 1 d . . . . .
H6 H 0.7888 0.6731 0.3891 0.019 Uiso 1 1 calc R U . . .
C7 C 1.14621(9) 0.55629(16) 0.31085(8) 0.0237(2) Uani 1 1 d . . . . .
H7A H 1.1790 0.6323 0.2631 0.028 Uiso 1 1 calc R U . . .
H7B H 1.1712 0.4304 0.3011 0.028 Uiso 1 1 calc R U . . .
C8 C 1.19361(10) 0.61850(18) 0.40521(9) 0.0316(3) Uani 1 1 d . . . . .
H8A H 1.2757 0.6093 0.4081 0.047 Uiso 1 1 calc R U . . .
H8B H 1.1718 0.7444 0.4152 0.047 Uiso 1 1 calc R U . . .
H8C H 1.1640 0.5420 0.4533 0.047 Uiso 1 1 calc R U . . .
C9 C 0.66816(8) 0.56199(13) 0.24537(7) 0.01433(19) Uani 1 1 d . . . . .
C10 C 0.60495(8) 0.48489(13) 0.31364(6) 0.01552(19) Uani 1 1 d D . . . .
O10 O 0.66046(6) 0.41581(11) 0.39031(5) 0.02168(17) Uani 1 1 d D . . . .
H10 H 0.6159(13) 0.369(2) 0.4248(10) 0.033 Uiso 1 1 d D U . . .
C11 C 0.48865(8) 0.47994(14) 0.29713(7) 0.0181(2) Uani 1 1 d . . . . .
H11 H 0.4434 0.4311 0.3428 0.022 Uiso 1 1 calc R U . . .
C12 C 0.43826(8) 0.54555(14) 0.21485(7) 0.0183(2) Uani 1 1 d . . . . .
H12 H 0.3589 0.5412 0.2047 0.022 Uiso 1 1 calc R U . . .
C13 C 0.50296(8) 0.61802(13) 0.14668(7) 0.0173(2) Uani 1 1 d D . . . .
O13 O 0.45648(6) 0.68575(12) 0.06532(5) 0.02552(18) Uani 1 1 d D . . . .
H13 H 0.3875(11) 0.666(2) 0.0618(11) 0.038 Uiso 1 1 d D U . . .
C14 C 0.61900(8) 0.62732(13) 0.16210(7) 0.0162(2) Uani 1 1 d . . . . .
H14 H 0.6640 0.6774 0.1166 0.019 Uiso 1 1 calc R U . . .
O1W O 0.54826(7) 0.24137(12) 0.51117(6) 0.02601(18) Uani 1 1 d D . . . .
H1W1 H 0.4818(11) 0.212(2) 0.4960(11) 0.039 Uiso 1 1 d D U . . .
H1W2 H 0.5859(12) 0.145(2) 0.5218(12) 0.039 Uiso 1 1 d D 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 C6 1.3565(12) . ?
N1 C2 1.3573(12) . ?
N1 C9 1.4511(12) . ?
C2 C3 1.3688(13) . ?
C2 H2 0.9500 . ?
C3 C4 1.3986(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3956(14) . ?
C4 C7 1.5031(13) . ?
C5 C6 1.3775(14) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.5156(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C14 1.3924(13) . ?
C9 C10 1.4007(13) . ?
C10 O10 1.3553(12) . ?
C10 C11 1.3942(13) . ?
O10 H10 0.828(13) . ?
C11 C12 1.3867(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3967(14) . ?
C12 H12 0.9500 . ?
C13 O13 1.3641(12) . ?
C13 C14 1.3908(13) . ?
O13 H13 0.835(13) . ?
C14 H14 0.9500 . ?
O1W H1W1 0.838(13) . ?
O1W H1W2 0.853(13) . ?

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
C6 N1 C2 120.36(8) . . ?
C6 N1 C9 119.88(8) . . ?
C2 N1 C9 119.74(8) . . ?
N1 C2 C3 120.37(9) . . ?
N1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C2 C3 C4 120.88(9) . . ?
C2 C3 H3 119.6 . . ?
C4 C3 H3 119.6 . . ?
C5 C4 C3 117.46(9) . . ?
C5 C4 C7 122.89(9) . . ?
C3 C4 C7 119.64(9) . . ?
C6 C5 C4 120.24(9) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
N1 C6 C5 120.68(9) . . ?
N1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C4 C7 C8 115.97(9) . . ?
C4 C7 H7A 108.3 . . ?
C8 C7 H7A 108.3 . . ?
C4 C7 H7B 108.3 . . ?
C8 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C14 C9 C10 122.29(9) . . ?
C14 C9 N1 119.43(8) . . ?
C10 C9 N1 118.24(8) . . ?
O10 C10 C11 124.10(9) . . ?
O10 C10 C9 118.20(9) . . ?
C11 C10 C9 117.68(9) . . ?
C10 O10 H10 110.5(10) . . ?
C12 C11 C10 120.76(9) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
C11 C12 C13 120.70(9) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
O13 C13 C14 117.86(9) . . ?
O13 C13 C12 122.45(9) . . ?
C14 C13 C12 119.66(9) . . ?
C13 O13 H13 109.5(11) . . ?
C13 C14 C9 118.88(9) . . ?
C13 C14 H14 120.6 . . ?
C9 C14 H14 120.6 . . ?
H1W1 O1W H1W2 108.2(14) . . ?

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
C6 N1 C2 C3 1.23(14) . . . . ?
C9 N1 C2 C3 -177.11(9) . . . . ?
N1 C2 C3 C4 -0.12(15) . . . . ?
C2 C3 C4 C5 -0.90(15) . . . . ?
C2 C3 C4 C7 179.74(10) . . . . ?
C3 C4 C5 C6 0.84(15) . . . . ?
C7 C4 C5 C6 -179.82(9) . . . . ?
C2 N1 C6 C5 -1.29(14) . . . . ?
C9 N1 C6 C5 177.05(9) . . . . ?
C4 C5 C6 N1 0.23(15) . . . . ?
C5 C4 C7 C8 2.23(16) . . . . ?
C3 C4 C7 C8 -178.45(10) . . . . ?
C6 N1 C9 C14 133.84(10) . . . . ?
C2 N1 C9 C14 -47.82(12) . . . . ?
C6 N1 C9 C10 -48.34(12) . . . . ?
C2 N1 C9 C10 130.00(10) . . . . ?
C14 C9 C10 O10 176.40(9) . . . . ?
N1 C9 C10 O10 -1.35(13) . . . . ?
C14 C9 C10 C11 -1.95(14) . . . . ?
N1 C9 C10 C11 -179.71(8) . . . . ?
O10 C10 C11 C12 -176.79(10) . . . . ?
C9 C10 C11 C12 1.46(15) . . . . ?
C10 C11 C12 C13 0.02(16) . . . . ?
C11 C12 C13 O13 -179.24(10) . . . . ?
C11 C12 C13 C14 -1.10(15) . . . . ?
O13 C13 C14 C9 178.86(9) . . . . ?
C12 C13 C14 C9 0.64(15) . . . . ?
C10 C9 C14 C13 0.91(15) . . . . ?
N1 C9 C14 C13 178.64(8) . . . . ?

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
C2 H2 Cl1 0.95 2.64 3.5494(10) 159.9 3_665
C5 H5 O13 0.95 2.40 3.2510(12) 149.0 4_676
C6 H6 Cl1 0.95 2.93 3.8519(10) 163.5 4_676
O10 H10 O1W 0.828(13) 1.797(13) 2.6086(11) 166.5(15) .
O13 H13 Cl1 0.835(13) 2.282(13) 3.1150(8) 175.4(15) .
O1W H1W1 Cl1 0.838(13) 2.291(13) 3.1275(8) 176.8(16) 2_545
O1W H1W2 Cl1 0.853(13) 2.376(13) 3.2271(9) 175.3(16) 4_666

_refine_diff_density_max         0.277
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.052



