#------------------------------------------------------------------------------
#$Date: 2023-09-19 04:36:44 +0300 (Tue, 19 Sep 2023) $
#$Revision: 286395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/23/2312304.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2312304
loop_
_publ_author_name
'Kennedy, Alan R.'
'Cruickshank, Laura'
'Maher, Pamela'
'McKinnon, Zoe'
_publ_section_title
;
 A structural comparison of salt forms of dopamine with the structures of
 other phenylethylamines.
;
_journal_coeditor_code           OP3027
_journal_issue                   10
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229623007696
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C8 H12 N1 O2 +, C6 H5 O4 S1 -, H2 O1'
_chemical_formula_moiety         'C8 H12 N1 O2 +, C6 H5 O4 S1 -, H2 O1'
_chemical_formula_sum            'C14 H19 N O7 S'
_chemical_formula_weight         345.36
_chemical_name_common
;
Dopamine 4-hydroxybenzenesulfonate monohydrate
;
_chemical_name_systematic
;
2-(3,4-Dihydroxyphenyl)ethan-1-aminium 4-hydroxybenzenesulfonate monohydrate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 95.273(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.4085(8)
_cell_length_b                   11.9234(5)
_cell_length_c                   7.6779(3)
_cell_measurement_reflns_used    2384
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      72.9932
_cell_measurement_theta_min      4.4971
_cell_volume                     1586.95(12)
_computing_cell_refinement
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL in WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Oxford Diffraction Gemini S'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0532
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            6603
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         73.144
_diffrn_reflns_theta_min         4.501
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.153
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.446
_exptl_crystal_description       'cut lath'
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.808
_refine_diff_density_min         -0.406
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0571
_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)+(0.1070P)²+0.1388P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1507
_refine_ls_wR_factor_ref         0.1688
_reflns_number_gt                2474
_reflns_number_total             3113
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            op3027sup1.cif
_cod_data_source_block           IV
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2312304
_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'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.31573(4) 0.39989(5) 0.60904(7) 0.0224(2) Uani d 1 . .
O O1 -0.11995(11) -0.01838(17) 0.8196(3) 0.0286(4) Uani d 1 . .
O O2 -0.19486(11) 0.15240(17) 0.6330(3) 0.0299(5) Uani d 1 . .
O O3 0.27420(11) 0.43408(18) 0.7561(3) 0.0308(5) Uani d 1 . .
O O4 0.31045(11) 0.48640(17) 0.4714(2) 0.0266(4) Uani d 1 . .
O O5 0.29390(12) 0.29108(17) 0.5367(3) 0.0308(5) Uani d 1 . .
O O6 0.64350(13) 0.37956(18) 0.8833(3) 0.0360(5) Uani d 1 . .
O O1W 0.27025(12) 0.69308(17) 0.5738(3) 0.0315(5) Uani d 1 . .
N N1 0.25024(14) 0.0775(2) 0.6281(3) 0.0255(5) Uani d 1 . .
C C9 0.41447(15) 0.3914(2) 0.6877(3) 0.0222(5) Uani d 1 . .
C C6 -0.11546(16) 0.1565(2) 0.6607(3) 0.0259(6) Uani d 1 . .
C C1 0.16405(16) 0.0764(2) 0.6140(3) 0.0266(6) Uani d 1 . .
H H1A 0.145838 -0.001595 0.626794 0.032 Uiso calc 1 . .
H H1B 0.144028 0.103494 0.496643 0.032 Uiso calc 1 . .
C C2 0.13242(16) 0.1494(2) 0.7523(3) 0.0267(6) Uani d 1 . .
H H2A 0.153259 0.226421 0.745624 0.032 Uiso calc 1 . .
H H2B 0.148574 0.119018 0.870012 0.032 Uiso calc 1 . .
C C4 0.00070(16) 0.0649(2) 0.7806(3) 0.0244(5) Uani d 1 . .
H H4 0.025452 0.002839 0.839654 0.029 Uiso calc 1 . .
C C12 0.56822(16) 0.3803(2) 0.8163(4) 0.0263(6) Uani d 1 . .
C C5 -0.07927(16) 0.0670(2) 0.7523(3) 0.0229(5) Uani d 1 . .
C C7 -0.07172(17) 0.2442(2) 0.6040(4) 0.0295(6) Uani d 1 . .
H H7 -0.096434 0.305605 0.543098 0.035 Uiso calc 1 . .
C C8 0.00801(17) 0.2426(2) 0.6361(4) 0.0285(6) Uani d 1 . .
H H8 0.037566 0.303407 0.598122 0.034 Uiso calc 1 . .
C C3 0.04508(16) 0.1524(2) 0.7237(3) 0.0238(5) Uani d 1 . .
C C11 0.5229(3) 0.4732(5) 0.8581(7) 0.0282(13) Uani d 0.503(5) A 1
H H11 0.544809 0.531986 0.929891 0.034 Uiso calc 0.503(5) A 1
C C13 0.5367(3) 0.2934(5) 0.7181(8) 0.0263(13) Uani d 0.503(5) A 1
H H13 0.567283 0.230072 0.695150 0.032 Uiso calc 0.503(5) A 1
C C14 0.4587(3) 0.2980(4) 0.6512(7) 0.0260(13) Uani d 0.503(5) A 1
H H14 0.436354 0.238259 0.581989 0.031 Uiso calc 0.503(5) A 1
C C10 0.4459(3) 0.4773(5) 0.7929(7) 0.0278(13) Uani d 0.503(5) A 1
H H10 0.414731 0.539082 0.820398 0.033 Uiso calc 0.503(5) A 1
C C10A 0.4634(3) 0.4819(5) 0.6575(7) 0.0242(12) Uani d 0.497(5) A 2
H H10A 0.444006 0.546019 0.594667 0.029 Uiso calc 0.497(5) A 2
C C11A 0.5408(3) 0.4758(5) 0.7211(7) 0.0281(13) Uani d 0.497(5) A 2
H H11A 0.574896 0.535508 0.700573 0.034 Uiso calc 0.497(5) A 2
C C14A 0.4415(3) 0.2978(5) 0.7743(7) 0.0240(12) Uani d 0.497(5) A 2
H H14A 0.407490 0.237325 0.791765 0.029 Uiso calc 0.497(5) A 2
C C13A 0.5190(3) 0.2905(4) 0.8374(7) 0.0247(12) Uani d 0.497(5) A 2
H H13A 0.538135 0.224221 0.894819 0.030 Uiso calc 0.497(5) A 2
H H1H -0.1688(8) -0.009(3) 0.785(5) 0.032(9) Uiso d 1 . .
H H2H -0.211(2) 0.206(2) 0.559(4) 0.039(10) Uiso d 1 . .
H H1N 0.268(2) 0.056(3) 0.731(5) 0.032(9) Uiso d 1 . .
H H2N 0.2645(19) 0.146(3) 0.610(4) 0.025(8) Uiso d 1 . .
H H3N 0.268(2) 0.037(3) 0.547(5) 0.041(10) Uiso d 1 . .
H H3H 0.663(2) 0.3119(16) 0.891(5) 0.047(11) Uiso d 1 . .
H H1W 0.247(2) 0.676(4) 0.666(4) 0.057(13) Uiso d 1 . .
H H2W 0.284(2) 0.6270(18) 0.537(5) 0.050(12) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O5 S1 O3 . . 114.67(13) ?
O5 S1 O4 . . 110.80(11) ?
O3 S1 O4 . . 110.98(12) ?
O5 S1 C9 . . 106.98(12) ?
O3 S1 C9 . . 106.68(12) ?
O4 S1 C9 . . 106.20(12) ?
C5 O1 H1H . . 108(2) ?
C6 O2 H2H . . 109(2) ?
C12 O6 H3H . . 113(3) ?
H1W O1W H2W . . 102(4) ?
C1 N1 H1N . . 110(2) ?
C1 N1 H2N . . 107(2) ?
H1N N1 H2N . . 110(3) ?
C1 N1 H3N . . 111(3) ?
H1N N1 H3N . . 112(3) ?
H2N N1 H3N . . 106(3) ?
C10 C9 C14 . . 120.8(4) ?
C14A C9 C10A . . 121.5(4) ?
C14A C9 S1 . . 119.6(3) ?
C10 C9 S1 . . 118.4(3) ?
C14 C9 S1 . . 120.8(3) ?
C10A C9 S1 . . 118.9(3) ?
O2 C6 C7 . . 123.3(2) ?
O2 C6 C5 . . 116.7(2) ?
C7 C6 C5 . . 119.9(3) ?
N1 C1 C2 . . 111.8(2) ?
N1 C1 H1A . . 109.3 ?
C2 C1 H1A . . 109.3 ?
N1 C1 H1B . . 109.3 ?
C2 C1 H1B . . 109.3 ?
H1A C1 H1B . . 107.9 ?
C1 C2 C3 . . 109.6(2) ?
C1 C2 H2A . . 109.8 ?
C3 C2 H2A . . 109.8 ?
C1 C2 H2B . . 109.8 ?
C3 C2 H2B . . 109.8 ?
H2A C2 H2B . . 108.2 ?
C5 C4 C3 . . 120.9(3) ?
C5 C4 H4 . . 119.5 ?
C3 C4 H4 . . 119.5 ?
O6 C12 C13 . . 121.8(3) ?
O6 C12 C13A . . 122.2(3) ?
O6 C12 C11A . . 117.9(3) ?
C13A C12 C11A . . 119.9(4) ?
O6 C12 C11 . . 117.2(3) ?
C13 C12 C11 . . 121.0(4) ?
O1 C5 C4 . . 118.2(2) ?
O1 C5 C6 . . 122.3(2) ?
C4 C5 C6 . . 119.5(2) ?
C6 C7 C8 . . 120.2(3) ?
C6 C7 H7 . . 119.9 ?
C8 C7 H7 . . 119.9 ?
C7 C8 C3 . . 120.5(3) ?
C7 C8 H8 . . 119.8 ?
C3 C8 H8 . . 119.8 ?
C4 C3 C8 . . 118.9(3) ?
C4 C3 C2 . . 121.0(2) ?
C8 C3 C2 . . 120.1(2) ?
C10 C11 C12 . . 119.1(5) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
C12 C13 C14 . . 119.8(5) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C9 C14 C13 . . 119.2(5) ?
C9 C14 H14 . . 120.4 ?
C13 C14 H14 . . 120.4 ?
C9 C10 C11 . . 120.1(5) ?
C9 C10 H10 . . 120.0 ?
C11 C10 H10 . . 120.0 ?
C11A C10A C9 . . 118.9(5) ?
C11A C10A H10A . . 120.5 ?
C9 C10A H10A . . 120.5 ?
C10A C11A C12 . . 119.6(5) ?
C10A C11A H11A . . 120.2 ?
C12 C11A H11A . . 120.2 ?
C9 C14A C13A . . 120.1(4) ?
C9 C14A H14A . . 120.0 ?
C13A C14A H14A . . 120.0 ?
C12 C13A C14A . . 119.9(5) ?
C12 C13A H13A . . 120.0 ?
C14A C13A H13A . . 120.0 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O5 . 1.448(2) ?
S1 O3 . 1.454(2) ?
S1 O4 . 1.4734(19) ?
S1 C9 . 1.772(3) ?
O1 C5 . 1.369(3) ?
O1 H1H . 0.874(10) ?
O2 C6 . 1.380(3) ?
O2 H2H . 0.880(10) ?
O6 C12 . 1.363(3) ?
O6 H3H . 0.876(10) ?
O1W H1W . 0.876(10) ?
O1W H2W . 0.878(10) ?
N1 C1 . 1.495(3) ?
N1 H1N . 0.86(4) ?
N1 H2N . 0.86(4) ?
N1 H3N . 0.86(4) ?
C9 C14A . 1.361(6) ?
C9 C10 . 1.385(6) ?
C9 C14 . 1.397(6) ?
C9 C10A . 1.407(6) ?
C6 C7 . 1.387(4) ?
C6 C5 . 1.396(4) ?
C1 C2 . 1.516(4) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.517(4) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C4 C5 . 1.389(4) ?
C4 C3 . 1.393(4) ?
C4 H4 . 0.9500 ?
C12 C13 . 1.366(6) ?
C12 C13A . 1.391(6) ?
C12 C11A . 1.412(6) ?
C12 C11 . 1.414(6) ?
C7 C8 . 1.387(4) ?
C7 H7 . 0.9500 ?
C8 C3 . 1.395(4) ?
C8 H8 . 0.9500 ?
C11 C10 . 1.387(8) ?
C11 H11 . 0.9500 ?
C13 C14 . 1.408(8) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C10 H10 . 0.9500 ?
C10A C11A . 1.391(8) ?
C10A H10A . 0.9500 ?
C11A H11A . 0.9500 ?
C14A C13A . 1.393(7) ?
C14A H14A . 0.9500 ?
C13A H13A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O1 H1H O2 . 0.874(10) 2.28(3) 2.749(3) 114(3) yes
O1 H1H O3 2_546 0.874(10) 1.953(19) 2.754(3) 152(3) yes
O2 H2H O1W 3_566 0.880(10) 1.836(15) 2.693(3) 164(4) yes
N1 H1N O4 4_566 0.86(4) 1.99(4) 2.850(3) 178(4) yes
N1 H2N O5 . 0.86(4) 1.91(4) 2.766(3) 172(3) yes
N1 H3N O3 4_565 0.86(4) 2.27(4) 2.927(3) 133(3) yes
N1 H3N O6 2_646 0.86(4) 2.46(4) 3.005(3) 122(3) yes
O6 H3H O1W 2_646 0.876(10) 1.834(16) 2.686(3) 164(4) yes
O1W H1W O2 2_556 0.876(10) 1.878(11) 2.752(3) 175(4) yes
O1W H2W O4 . 0.878(10) 1.821(11) 2.698(3) 177(4) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O5 S1 C9 C14A . . . . -41.3(3) ?
O3 S1 C9 C14A . . . . 81.9(3) ?
O4 S1 C9 C14A . . . . -159.6(3) ?
O5 S1 C9 C10 . . . . -167.9(3) ?
O3 S1 C9 C10 . . . . -44.7(3) ?
O4 S1 C9 C10 . . . . 73.7(3) ?
O5 S1 C9 C14 . . . . 9.2(3) ?
O3 S1 C9 C14 . . . . 132.4(3) ?
O4 S1 C9 C14 . . . . -109.2(3) ?
O5 S1 C9 C10A . . . . 138.1(3) ?
O3 S1 C9 C10A . . . . -98.7(3) ?
O4 S1 C9 C10A . . . . 19.8(3) ?
N1 C1 C2 C3 . . . . 175.7(2) ?
C3 C4 C5 O1 . . . . -176.5(2) ?
C3 C4 C5 C6 . . . . 2.0(4) ?
O2 C6 C5 O1 . . . . -3.1(4) ?
C7 C6 C5 O1 . . . . 176.2(2) ?
O2 C6 C5 C4 . . . . 178.4(2) ?
C7 C6 C5 C4 . . . . -2.2(4) ?
O2 C6 C7 C8 . . . . -179.8(2) ?
C5 C6 C7 C8 . . . . 0.9(4) ?
C6 C7 C8 C3 . . . . 0.7(4) ?
C5 C4 C3 C8 . . . . -0.4(4) ?
C5 C4 C3 C2 . . . . -179.2(2) ?
C7 C8 C3 C4 . . . . -0.9(4) ?
C7 C8 C3 C2 . . . . 177.8(2) ?
C1 C2 C3 C4 . . . . 80.3(3) ?
C1 C2 C3 C8 . . . . -98.4(3) ?
O6 C12 C11 C10 . . . . -179.9(4) ?
C13 C12 C11 C10 . . . . -2.3(7) ?
O6 C12 C13 C14 . . . . -179.8(4) ?
C11 C12 C13 C14 . . . . 2.7(7) ?
C10 C9 C14 C13 . . . . -2.0(7) ?
S1 C9 C14 C13 . . . . -179.0(4) ?
C12 C13 C14 C9 . . . . -0.5(8) ?
C14 C9 C10 C11 . . . . 2.4(7) ?
S1 C9 C10 C11 . . . . 179.5(4) ?
C12 C11 C10 C9 . . . . -0.3(8) ?
C14A C9 C10A C11A . . . . -1.4(7) ?
S1 C9 C10A C11A . . . . 179.3(4) ?
C9 C10A C11A C12 . . . . -0.9(7) ?
O6 C12 C11A C10A . . . . -177.1(4) ?
C13A C12 C11A C10A . . . . 3.6(7) ?
C10A C9 C14A C13A . . . . 0.9(7) ?
S1 C9 C14A C13A . . . . -179.7(4) ?
O6 C12 C13A C14A . . . . 176.6(4) ?
C11A C12 C13A C14A . . . . -4.1(7) ?
C9 C14A C13A C12 . . . . 1.8(7) ?

_cod_database_fobs_code 2312304
