#------------------------------------------------------------------------------
#$Date: 2025-08-19 09:12:48 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301798 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/92/2019268.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_2019268
loop_
_publ_author_name
'Lopez de Diego, Heidi'
'Koradia, Vishal'
'Bond, Andrew D.'
_publ_section_title
;
 Enantiotropically related polymorphs of gaboxadol hydrochloride
;
_journal_coeditor_code           FM3008
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1234
_journal_page_last               1237
_journal_paper_doi               10.1107/S0108270113025961
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C6 H9 N2 O2 + , Cl -'
_chemical_formula_moiety         'C6 H9 N2 O2 +, Cl -'
_chemical_formula_sum            'C6 H9 Cl N2 O2'
_chemical_formula_weight         176.60
_chemical_name_common            'Gaboxadol hydrochloride'
_chemical_name_systematic
;
3-Hydroxy-4,5,6,7-tetrahydro-1,2-oxazolo[5,4-c]pyridin-6-ium chloride
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_space_group_name_H-M   'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.4200(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.1489(5)
_cell_length_b                   6.5780(2)
_cell_length_c                   17.0721(9)
_cell_measurement_reflns_used    5388
_cell_measurement_temperature    220(2)
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.39
_cell_volume                     1476.59(11)
_computing_cell_refinement       'SAINT (Bruker, 2010)'
_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_data_reduction        'SAINT (Bruker, 2010)'
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al.,
2008)
;
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      220(2)
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker Nonius X8 APEXII CCD area-detector'
_diffrn_measurement_method       'thin-slice ω and φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0179
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12044
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.90
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.464
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.855
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       lath
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.171
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     112
_refine_ls_number_reflns         1643
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0264
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0369P)²+0.9569P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0719
_refine_ls_wR_factor_ref         0.0751
_reflns_number_gt                1359
_reflns_number_total             1643
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fm3008.cif
_cod_data_source_block           LT
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               2019268
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
Cl Cl1 0.12433(3) 0.77808(5) 0.199929(19) 0.02848(13) Uani d . 1 1
O O1 0.12661(9) -0.10490(16) 0.53688(6) 0.0313(3) Uani d D 1 1
H H1 0.1223(18) -0.139(4) 0.5828(7) 0.074(7) Uiso d D 1 1
O O2 0.11882(8) 0.42094(15) 0.54553(6) 0.0291(2) Uani d . 1 1
N N1 0.11916(10) 0.22652(18) 0.58347(7) 0.0280(3) Uani d . 1 1
N N2 0.09024(10) 0.46912(19) 0.33423(7) 0.0268(3) Uani d D 1 1
H H2A 0.0222(8) 0.435(3) 0.3349(10) 0.041(5) Uiso d D 1 1
H H2B 0.0994(15) 0.568(2) 0.2970(10) 0.058(6) Uiso d D 1 1
C C1 0.12381(10) 0.0953(2) 0.52597(8) 0.0231(3) Uani d . 1 1
C C2 0.12656(10) 0.1884(2) 0.45062(8) 0.0223(3) Uani d . 1 1
C C3 0.12312(10) 0.3868(2) 0.46755(8) 0.0231(3) Uani d . 1 1
C C4 0.12171(11) 0.5582(2) 0.41102(8) 0.0266(3) Uani d . 1 1
H H4A 0.1893 0.6199 0.4072 0.032 Uiso calc R 1 1
H H4B 0.0732 0.6626 0.4275 0.032 Uiso calc R 1 1
C C5 0.15045(12) 0.2838(2) 0.31278(8) 0.0296(3) Uani d . 1 1
H H5A 0.2231 0.3168 0.3141 0.036 Uiso calc R 1 1
H H5B 0.1327 0.2424 0.2593 0.036 Uiso calc R 1 1
C C6 0.12991(11) 0.1074(2) 0.36880(7) 0.0261(3) Uani d . 1 1
H H6A 0.0649 0.0427 0.3554 0.031 Uiso calc R 1 1
H H6B 0.1839 0.0053 0.3644 0.031 Uiso calc R 1 1
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 O1 H1 113.6(18)
C3 O2 N1 107.27(10)
C1 N1 O2 104.45(11)
C4 N2 C5 112.96(11)
C4 N2 H2A 110.4(11)
C5 N2 H2A 108.6(11)
C4 N2 H2B 107.1(13)
C5 N2 H2B 109.5(13)
H2A N2 H2B 108.2(16)
N1 C1 O1 123.31(13)
N1 C1 C2 113.26(12)
O1 C1 C2 123.43(12)
C3 C2 C1 102.90(12)
C3 C2 C6 123.40(12)
C1 C2 C6 133.68(12)
C2 C3 O2 112.12(12)
C2 C3 C4 126.94(13)
O2 C3 C4 120.94(12)
C3 C4 N2 105.99(11)
C3 C4 H4A 110.5
N2 C4 H4A 110.5
C3 C4 H4B 110.5
N2 C4 H4B 110.5
H4A C4 H4B 108.7
N2 C5 C6 111.59(11)
N2 C5 H5A 109.3
C6 C5 H5A 109.3
N2 C5 H5B 109.3
C6 C5 H5B 109.3
H5A C5 H5B 108.0
C2 C6 C5 108.69(11)
C2 C6 H6A 110.0
C5 C6 H6A 110.0
C2 C6 H6B 110.0
C5 C6 H6B 110.0
H6A C6 H6B 108.3
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3303(18)
O1 H1 0.817(10)
O2 C3 1.3518(16)
O2 N1 1.4336(15)
N1 C1 1.3091(18)
N2 C4 1.4915(18)
N2 C5 1.5006(19)
N2 H2A 0.923(9)
N2 H2B 0.917(9)
C1 C2 1.4255(19)
C2 C3 1.338(2)
C2 C6 1.4959(18)
C3 C4 1.484(2)
C4 H4A 0.9800
C4 H4B 0.9800
C5 C6 1.5288(19)
C5 H5A 0.9800
C5 H5B 0.9800
C6 H6A 0.9800
C6 H6B 0.9800
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
N2 H2B Cl1 . 0.920(10) 2.190(10) 3.0990(12) 174.2(18)
N2 H2A Cl1 4_445 0.920(10) 2.260(10) 3.1393(13) 158.8(15)
O1 H1 Cl1 8 0.820(10) 2.200(10) 3.0080(11) 170(2)
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
C3 O2 N1 C1 0.16(14)
O2 N1 C1 O1 179.36(12)
O2 N1 C1 C2 -0.08(15)
N1 C1 C2 C3 -0.03(16)
O1 C1 C2 C3 -179.46(13)
N1 C1 C2 C6 -178.66(15)
O1 C1 C2 C6 1.9(2)
C1 C2 C3 O2 0.14(16)
C6 C2 C3 O2 178.95(12)
C1 C2 C3 C4 -178.63(13)
C6 C2 C3 C4 0.2(2)
N1 O2 C3 C2 -0.19(16)
N1 O2 C3 C4 178.66(12)
C2 C3 C4 N2 18.4(2)
O2 C3 C4 N2 -160.22(12)
C5 N2 C4 C3 -49.92(15)
C4 N2 C5 C6 66.15(16)
C3 C2 C6 C5 11.38(19)
C1 C2 C6 C5 -170.22(15)
N2 C5 C6 C2 -42.02(16)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139061704
