#------------------------------------------------------------------------------
#$Date: 2023-09-19 04:36:44 +0300 (Tue, 19 Sep 2023) $
#$Revision: 286395 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/23/2312303.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_2312303
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          '2C8 H12 N1 O2 +, C2 H4 O6 S2 2-'
_chemical_formula_moiety         '2(C8 H12 N1 O2 +), C2 H4 O6 S2 2-'
_chemical_formula_sum            'C18 H28 N2 O10 S2'
_chemical_formula_weight         496.54
_chemical_name_common
;
Dopamine ethanedisulfonate
;
_chemical_name_systematic
;
2-(3,4-Dihydroxyphenyl)ethan-1-aminium ethane-1,2-disulfonate
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6328(5)
_cell_length_b                   8.5651(5)
_cell_length_c                   23.8669(13)
_cell_measurement_reflns_used    3597
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      74.6837
_cell_measurement_theta_min      3.7011
_cell_volume                     2173.6(2)
_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 0.999
_diffrn_measured_fraction_theta_max 0.973
_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  0.0324
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7583
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         74.856
_diffrn_reflns_theta_min         3.704
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.754
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2019)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_description       slab
_exptl_crystal_F_000             1048
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.569
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.138
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0781P)²+1.1139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1342
_reflns_number_gt                1924
_reflns_number_total             2172
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            op3027sup1.cif
_cod_data_source_block           III
_cod_database_code               2312303
_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'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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 0.67052(4) 0.63900(5) 1.00071(2) 0.0157(2) Uani d 1 . .
O O1 0.44177(14) 0.44564(19) 0.85879(6) 0.0250(4) Uani d 1 . .
O O2 0.63054(14) 0.24475(17) 0.88987(6) 0.0219(3) Uani d 1 . .
O O3 0.63463(14) 0.73346(17) 1.04876(6) 0.0236(4) Uani d 1 . .
O O4 0.64846(13) 0.71856(17) 0.94706(6) 0.0212(3) Uani d 1 . .
O O5 0.79810(15) 0.57875(18) 1.00334(5) 0.0211(4) Uani d 1 . .
N N1 0.50796(17) 0.4682(2) 0.57846(7) 0.0195(4) Uani d 1 . .
C C1 0.5254(2) 0.4025(3) 0.63567(8) 0.0231(4) Uani d 1 . .
H H1A 0.558048 0.294597 0.632664 0.028 Uiso calc 1 . .
H H1B 0.442950 0.398005 0.654908 0.028 Uiso calc 1 . .
C C2 0.61585(19) 0.4999(2) 0.67027(8) 0.0206(4) Uani d 1 . .
H H2A 0.700116 0.498691 0.652638 0.025 Uiso calc 1 . .
H H2B 0.586209 0.609429 0.671606 0.025 Uiso calc 1 . .
C C3 0.62440(18) 0.4351(2) 0.72921(8) 0.0190(4) Uani d 1 . .
C C4 0.53191(19) 0.4718(2) 0.76855(8) 0.0199(4) Uani d 1 . .
H H4 0.466013 0.541546 0.758704 0.024 Uiso calc 1 . .
C C5 0.53525(17) 0.4074(2) 0.82203(8) 0.0188(4) Uani d 1 . .
C C6 0.63283(18) 0.3064(2) 0.83667(8) 0.0186(4) Uani d 1 . .
C C7 0.72407(18) 0.2677(2) 0.79749(8) 0.0214(4) Uani d 1 . .
H H7 0.789426 0.196986 0.807165 0.026 Uiso calc 1 . .
C C8 0.71985(18) 0.3322(2) 0.74412(8) 0.0212(4) Uani d 1 . .
H H8 0.782847 0.305750 0.717539 0.025 Uiso calc 1 . .
C C9 0.5686(2) 0.4744(2) 1.00146(7) 0.0191(5) Uani d 1 . .
H H9A 0.587986 0.406096 0.969125 0.023 Uiso calc 1 . .
H H9B 0.582627 0.413584 1.036173 0.023 Uiso calc 1 . .
H H1H 0.443(3) 0.383(3) 0.8861(12) 0.034(7) Uiso d 1 . .
H H1N 0.578(3) 0.470(3) 0.5576(11) 0.033(7) Uiso d 1 . .
H H2H 0.707(3) 0.228(3) 0.9040(12) 0.041(8) Uiso d 1 . .
H H2N 0.482(2) 0.563(3) 0.5787(9) 0.020(6) Uiso d 1 . .
H H3N 0.451(3) 0.415(4) 0.5588(12) 0.038(7) 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 . . 114.11(9) ?
O5 S1 O4 . . 110.58(8) ?
O3 S1 O4 . . 112.78(9) ?
O5 S1 C9 . . 106.68(10) ?
O3 S1 C9 . . 105.85(9) ?
O4 S1 C9 . . 106.21(9) ?
C5 O1 H1H . . 109.1(19) ?
C6 O2 H2H . . 113.2(18) ?
C1 N1 H1N . . 114.3(17) ?
C1 N1 H2N . . 113.1(15) ?
H1N N1 H2N . . 105(2) ?
C1 N1 H3N . . 112.1(18) ?
H1N N1 H3N . . 106(2) ?
H2N N1 H3N . . 106(2) ?
N1 C1 C2 . . 111.72(16) ?
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 ?
C3 C2 C1 . . 109.98(16) ?
C3 C2 H2A . . 109.7 ?
C1 C2 H2A . . 109.7 ?
C3 C2 H2B . . 109.7 ?
C1 C2 H2B . . 109.7 ?
H2A C2 H2B . . 108.2 ?
C8 C3 C4 . . 119.03(18) ?
C8 C3 C2 . . 120.91(17) ?
C4 C3 C2 . . 119.97(17) ?
C5 C4 C3 . . 120.65(18) ?
C5 C4 H4 . . 119.7 ?
C3 C4 H4 . . 119.7 ?
O1 C5 C4 . . 118.42(17) ?
O1 C5 C6 . . 121.93(17) ?
C4 C5 C6 . . 119.64(17) ?
O2 C6 C7 . . 122.86(17) ?
O2 C6 C5 . . 117.13(17) ?
C7 C6 C5 . . 119.96(18) ?
C6 C7 C8 . . 120.00(18) ?
C6 C7 H7 . . 120.0 ?
C8 C7 H7 . . 120.0 ?
C7 C8 C3 . . 120.69(18) ?
C7 C8 H8 . . 119.7 ?
C3 C8 H8 . . 119.7 ?
C9 C9 S1 5_667 . 110.76(19) ?
C9 C9 H9A 5_667 . 109.5 ?
S1 C9 H9A . . 109.5 ?
C9 C9 H9B 5_667 . 109.5 ?
S1 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
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 . 1.4527(16) ?
S1 O3 . 1.4544(14) ?
S1 O4 . 1.4693(14) ?
S1 C9 . 1.778(2) ?
O1 C5 . 1.366(2) ?
O1 H1H . 0.85(3) ?
O2 C6 . 1.375(2) ?
O2 H2H . 0.89(3) ?
N1 C1 . 1.488(2) ?
N1 H1N . 0.90(3) ?
N1 H2N . 0.85(3) ?
N1 H3N . 0.89(3) ?
C1 C2 . 1.518(3) ?
C1 H1A . 0.9900 ?
C1 H1B . 0.9900 ?
C2 C3 . 1.515(2) ?
C2 H2A . 0.9900 ?
C2 H2B . 0.9900 ?
C3 C8 . 1.390(3) ?
C3 C4 . 1.396(3) ?
C4 C5 . 1.391(3) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.396(3) ?
C6 C7 . 1.388(3) ?
C7 C8 . 1.389(3) ?
C7 H7 . 0.9500 ?
C8 H8 . 0.9500 ?
C9 C9 5_667 1.525(4) ?
C9 H9A . 0.9900 ?
C9 H9B . 0.9900 ?
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 . 0.85(3) 2.32(3) 2.746(2) 112(2) yes
O1 H1H O3 5_667 0.85(3) 2.02(3) 2.807(2) 154(3) yes
O2 H2H O4 7_755 0.89(3) 1.85(3) 2.727(2) 167(3) yes
N1 H1N O5 2_664 0.90(3) 1.89(3) 2.762(2) 163(2) yes
N1 H2N O2 4_656 0.85(3) 2.11(3) 2.890(2) 152(2) yes
N1 H2N O3 8_575 0.85(3) 2.49(3) 2.974(2) 117(2) yes
N1 H3N O4 4_646 0.89(3) 2.00(3) 2.776(2) 146(3) yes
N1 H3N O5 6_557 0.89(3) 2.61(3) 3.112(2) 117(2) 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
N1 C1 C2 C3 . . . . 176.39(16) ?
C1 C2 C3 C8 . . . . 95.6(2) ?
C1 C2 C3 C4 . . . . -81.0(2) ?
C8 C3 C4 C5 . . . . 0.4(3) ?
C2 C3 C4 C5 . . . . 176.98(17) ?
C3 C4 C5 O1 . . . . -179.24(18) ?
C3 C4 C5 C6 . . . . 0.7(3) ?
O1 C5 C6 O2 . . . . 0.7(3) ?
C4 C5 C6 O2 . . . . -179.24(17) ?
O1 C5 C6 C7 . . . . 178.33(18) ?
C4 C5 C6 C7 . . . . -1.6(3) ?
O2 C6 C7 C8 . . . . 178.95(17) ?
C5 C6 C7 C8 . . . . 1.5(3) ?
C6 C7 C8 C3 . . . . -0.4(3) ?
C4 C3 C8 C7 . . . . -0.5(3) ?
C2 C3 C8 C7 . . . . -177.11(18) ?
O5 S1 C9 C9 . . . 5_667 -179.75(15) ?
O3 S1 C9 C9 . . . 5_667 58.36(18) ?
O4 S1 C9 C9 . . . 5_667 -61.76(18) ?

_cod_database_fobs_code 2312303
