#------------------------------------------------------------------------------
#$Date: 2025-08-19 17:49:58 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301806 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/96/2239676.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_2239676
loop_
_publ_author_name
'Valerio-Cárdenas, Cintya'
'Hernández-Ortega, Simón'
'Morales-Morales, David'
_publ_section_title
;
 (tert-Butyl)(2-hydroxyethyl)ammonium chloride
;
_journal_coeditor_code           GW2144
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o783
_journal_paper_doi               10.1107/S1600536814012847
_journal_volume                  70
_journal_year                    2014
_chemical_formula_iupac          'C6 H16 N O +, Cl -'
_chemical_formula_moiety         'C6 H16 N O +, Cl -'
_chemical_formula_sum            'C6 H16 Cl N O'
_chemical_formula_weight         153.65
_chemical_name_systematic
;
(tert-Butyl)(2-hydroxyethyl)ammonium chloride
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 105.8040(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5204(3)
_cell_length_b                   7.8742(3)
_cell_length_c                   14.1844(5)
_cell_measurement_reflns_used    2475
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      25.25
_cell_measurement_theta_min      2.48
_cell_volume                     915.68(6)
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 0.83
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0579
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5487
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.298
_diffrn_reflns_theta_min         2.484
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.115
_exptl_crystal_description       prism
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.395
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.254
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     94
_refine_ls_number_reflns         1668
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0584P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1070
_refine_ls_wR_factor_ref         0.1235
_reflns_number_gt                1071
_reflns_number_total             1668
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gw2144sup1.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2239676
_cod_database_fobs_code          2239676
#BEGIN Tags that were not found in dictionaries:
_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.
;
_shelx_estimated_absorpt_t_min   0.873
_shelx_estimated_absorpt_t_max   0.989
_shelxl_version_number           20.13
#END Tags that were not found in dictionaries
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
Cl Cl1 0.44289(9) 0.82425(9) 0.62991(4) 0.0579(3) Uani d 1
O O1 0.2643(2) 0.8483(3) 0.92991(15) 0.0690(6) Uani d 1
H H1 0.303(4) 0.811(4) 0.9889(11) 0.083 Uiso d 1
C C1 0.3512(3) 0.7606(4) 0.87548(19) 0.0531(7) Uani d 1
H H1A 0.3003 0.7781 0.8062 0.064 Uiso calc 1
H H1B 0.3488 0.6400 0.8889 0.064 Uiso calc 1
C C2 0.5253(3) 0.8207(3) 0.90041(18) 0.0436(6) Uani d 1
H H2A 0.5280 0.9397 0.8832 0.052 Uiso calc 1
H H2B 0.5742 0.8098 0.9704 0.052 Uiso calc 1
N N3 0.6212(2) 0.7191(3) 0.84643(15) 0.0383(5) Uani d 1
H H3A 0.579(3) 0.734(3) 0.7818(8) 0.046 Uiso d 1
H H3B 0.607(3) 0.6079(13) 0.8511(17) 0.046 Uiso d 1
C C4 0.8038(3) 0.7496(3) 0.87151(19) 0.0454(7) Uani d 1
C C5 0.8775(3) 0.7126(4) 0.9796(2) 0.0686(9) Uani d 1
H H5A 0.8423 0.6028 0.9950 0.082 Uiso calc 1
H H5B 0.8427 0.7976 1.0181 0.082 Uiso calc 1
H H5C 0.9944 0.7142 0.9941 0.082 Uiso calc 1
C C6 0.8687(3) 0.6245(4) 0.8087(2) 0.0728(9) Uani d 1
H H6A 0.8452 0.5105 0.8247 0.087 Uiso calc 1
H H6B 0.9845 0.6386 0.8214 0.087 Uiso calc 1
H H6C 0.8172 0.6459 0.7407 0.087 Uiso calc 1
C C7 0.8344(3) 0.9303(4) 0.8456(2) 0.0678(9) Uani d 1
H H7A 0.9497 0.9489 0.8584 0.081 Uiso calc 1
H H7B 0.7906 1.0071 0.8844 0.081 Uiso calc 1
H H7C 0.7825 0.9498 0.7774 0.081 Uiso calc 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 104(2)
O1 C1 C2 110.7(2)
O1 C1 H1A 109.5
C2 C1 H1A 109.5
O1 C1 H1B 109.5
C2 C1 H1B 109.5
H1A C1 H1B 108.1
N3 C2 C1 110.6(2)
N3 C2 H2A 109.5
C1 C2 H2A 109.5
N3 C2 H2B 109.5
C1 C2 H2B 109.5
H2A C2 H2B 108.1
C2 N3 C4 117.61(19)
C2 N3 H3A 109.4(16)
C4 N3 H3A 108.7(16)
C2 N3 H3B 112.9(15)
C4 N3 H3B 106.6(15)
H3A N3 H3B 100(2)
C7 C4 N3 109.1(2)
C7 C4 C5 112.0(2)
N3 C4 C5 108.8(2)
C7 C4 C6 110.5(2)
N3 C4 C6 105.8(2)
C5 C4 C6 110.4(2)
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C4 C7 H7A 109.5
C4 C7 H7B 109.5
H7A C7 H7B 109.5
C4 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.390(3)
O1 H1 0.862(10)
C1 C2 1.504(4)
C1 H1A 0.9700
C1 H1B 0.9700
C2 N3 1.495(3)
C2 H2A 0.9700
C2 H2B 0.9700
N3 C4 1.518(3)
N3 H3A 0.896(9)
N3 H3B 0.888(10)
C4 C7 1.510(4)
C4 C5 1.519(4)
C4 C6 1.529(4)
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
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
O1 H1 Cl1 4_576 0.862(10) 2.294(13) 3.140(2) 167(3)
N3 H3A Cl1 . 0.896(9) 2.266(11) 3.144(2) 166(2)
N3 H3B Cl1 2_646 0.888(10) 2.304(10) 3.190(2) 175(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139086747
