##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_journal_date_recd_electronic     2023-07-13
_journal_date_accepted     2023-08-03
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2023
_journal_volume     79
_journal_issue      9
_journal_page_first     800
_journal_page_last     803
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989023006850
_journal_coeditor_code     WM5689
_publ_contact_author_name     'Shannon M. Biros'
_publ_contact_author_address
;
Department of Chemistry
Grand Valley State University
Allendale, MI 49401
USA
;
_publ_contact_author_email     'biross@gvsu.edu'
_publ_contact_author_fax     '616-331-3230'
_publ_contact_author_phone     '616-331-8955'
_publ_section_title
;
Crystal structure of a (carboxymethyl)triethylazanium
bromide--2-(triethylazaniumyl)acetate (1/1) hydrogen-bonded dimer
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Carlson, Faith M.' .
;
Department of Chemistry
Grand Valley State University
Allendale, MI 49401
USA
;
    'Staples, Richard J.' .
;
Center for Crystallographic Research
Department of Chemistry
Michigan State University
East Lansing, MI 48824
USA
;
    'Biros, Shannon M.' .
;
Department of Chemistry
Grand Valley State University
Allendale, MI 49401
USA
;
_publ_section_synopsis
;
The crystal structure of a hydrogen-bonded dimer of (triethylazaniumyl)acetic
acid and (triethylazaniumyl)acetate bromide features a carboxylic acid hydrogen
atom that is engaged in an asymmetric hydrogen bond with the carboxylate
oxygen. The crystal also features intramolecular C---H hydrogen bonds and a
layer of bromide ions that is surrounded by alkyl groups.
;
_chemical_name_systematic
;\
(Carboxymethyl)triethylazanium bromide--\
2-(triethylazaniumyl)acetate (1/1)
;
_chemical_name_common     ?
_chemical_formula_moiety     'C8 H18 N O2 +, Br -, C8 H17 N O2'
_chemical_formula_sum     'C16 H35 Br N2 O4'
_chemical_formula_iupac     'C8 H18 N O2 +, Br -, C8 H17 N O2'
_chemical_formula_weight     399.37
_chemical_melting_point     ?
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'I 1 2/a 1'
_space_group_name_Hall     '-I 2ya'
loop_
    _space_group_symop_operation_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'
_cell_length_a     12.6692(4)
_cell_length_b     7.0967(3)
_cell_length_c     22.3413(9)
_cell_angle_alpha     90
_cell_angle_beta     103.022(4)
_cell_angle_gamma     90
_cell_volume     1957.04(13)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     3269
_cell_measurement_theta_min     6.5540
_cell_measurement_theta_max     79.3860
_cell_measurement_temperature     100.00(10)
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.423
_exptl_crystal_size_mid     0.133
_exptl_crystal_size_min     0.023
_exptl_crystal_density_diffrn     1.355
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     ?
_exptl_crystal_F_000     848
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    8 -1 -5 0.0605
    -8 0 5 0.0549
    0 -5 -2 0.1838
    0 5 2 0.2345
    0 0 -1 0.0116
    0 0 1 0.0116
    8 1 -2 0.0946
    -7 2 5 0.0978
    -6 -3 1 0.1373
    7 -2 -5 0.1014
_exptl_absorpt_coefficient_mu     3.030
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
(CrysAlisPro; Oxford Diffraction, 2006)
;
_exptl_absorpt_correction_T_min     0.568
_exptl_absorpt_correction_T_max     1.000
_diffrn_ambient_temperature     100.15
_diffrn_source     ?
_diffrn_radiation_type     CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type     'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_device     'four-circle diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     6198
_diffrn_reflns_av_R_equivalents     0.0516
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_theta_min     4.062
_diffrn_reflns_theta_max     79.956
_diffrn_reflns_theta_full     67.684
_diffrn_measured_fraction_theta_max     0.935
_diffrn_measured_fraction_theta_full     0.979
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     16
_diffrn_reflns_limit_k_min     -8
_diffrn_reflns_limit_k_max     8
_diffrn_reflns_limit_l_min     -28
_diffrn_reflns_limit_l_max     25
_refine_special_details     ?
_reflns_number_total     1998
_reflns_number_gt     1785
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0447
_refine_ls_R_factor_gt     0.0396
_refine_ls_wR_factor_gt     0.1042
_refine_ls_wR_factor_ref     0.1086
_refine_ls_goodness_of_fit_ref     1.075
_refine_ls_restrained_S_all     1.075
_refine_ls_number_reflns     1998
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0638P)²+1.4873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.894
_refine_diff_density_min     -0.418
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    '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'
    'Br' 'Br' -0.6763 1.2805
                         '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'
    'O' 'O' 0.0492 0.0322
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection
;
CrysAlisPro (Oxford Diffraction, 2006)
;
_computing_cell_refinement
;
CrysAlisPro (Oxford Diffraction, 2006)
;
_computing_data_reduction
;
CrysAlisPro (Oxford Diffraction, 2006)
;
_computing_structure_solution
;
SHELXT  (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
CrystalMaker (Palmer, 2007)
;
_computing_publication_material
;
Olex2 (Dolomanov et al., 2009; Bourhis et al.,
2015)
;
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
    Br Br1 0.250000 0.39582(5) 0.500000 0.01824(16) Uani d 1 . .
    O O1 0.70415(15) 0.3474(3) 0.28191(9) 0.0250(4) Uani d 1 . .
    H H1 0.734798 0.280169 0.252098 0.07(3) Uiso d 0.5 A -1
    O O2 0.57904(15) 0.1209(3) 0.27312(9) 0.0235(4) Uani d 1 B -1
    N N1 0.49061(15) 0.3014(3) 0.36825(9) 0.0146(4) Uani d 1 B -1
    C C1 0.61984(19) 0.2698(4) 0.29428(11) 0.0181(5) Uani d 1 B -1
    C C2 0.57456(19) 0.3923(3) 0.33887(12) 0.0155(5) Uani d 1 B -1
    H H2A 0.635817 0.434190 0.372016 0.019 Uiso calc 1 B -1
    H H2B 0.542009 0.506334 0.316589 0.019 Uiso calc 1 B -1
    C C3 0.5279(2) 0.1112(3) 0.39641(12) 0.0187(5) Uani d 1 B -1
    H H3A 0.522278 0.017911 0.362887 0.022 Uiso calc 1 B -1
    H H3B 0.477980 0.070888 0.422252 0.022 Uiso calc 1 B -1
    C C4 0.6431(2) 0.1076(4) 0.43539(14) 0.0242(6) Uani d 1 B -1
    H H4A 0.694224 0.132344 0.409276 0.036 Uiso calc 1 B -1
    H H4B 0.658203 -0.016535 0.454658 0.036 Uiso calc 1 B -1
    H H4C 0.651144 0.204548 0.467320 0.036 Uiso calc 1 B -1
    C C5 0.47364(19) 0.4306(4) 0.41955(11) 0.0168(5) Uani d 1 B -1
    H H5A 0.419692 0.371758 0.439611 0.020 Uiso calc 1 B -1
    H H5B 0.542724 0.439647 0.450705 0.020 Uiso calc 1 B -1
    C C6 0.4358(2) 0.6278(4) 0.39983(14) 0.0255(6) Uani d 1 B -1
    H H6A 0.369669 0.621107 0.367223 0.038 Uiso calc 1 B -1
    H H6B 0.492434 0.693461 0.384459 0.038 Uiso calc 1 B -1
    H H6C 0.420881 0.696650 0.435042 0.038 Uiso calc 1 B -1
    C C7 0.38591(18) 0.2757(4) 0.31950(11) 0.0170(5) Uani d 1 B -1
    H H7A 0.360683 0.400804 0.302461 0.020 Uiso calc 1 B -1
    H H7B 0.401558 0.198822 0.285550 0.020 Uiso calc 1 B -1
    C C8 0.2954(2) 0.1824(4) 0.34289(13) 0.0242(6) Uani d 1 B -1
    H H8A 0.228952 0.182944 0.310402 0.036 Uiso calc 1 B -1
    H H8B 0.283092 0.251692 0.378634 0.036 Uiso calc 1 B -1
    H H8C 0.315681 0.052079 0.354755 0.036 Uiso calc 1 B -1
_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_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O1 H1 . 0.9686 ?
    O1 C1 . 1.286(3) ?
    O2 C1 . 1.224(3) ?
    N1 C2 . 1.514(3) ?
    N1 C3 . 1.519(3) ?
    N1 C5 . 1.520(3) ?
    N1 C7 . 1.526(3) ?
    C1 C2 . 1.528(3) ?
    C2 H2A . 0.9900 ?
    C2 H2B . 0.9900 ?
    C3 H3A . 0.9900 ?
    C3 H3B . 0.9900 ?
    C3 C4 . 1.522(4) ?
    C4 H4A . 0.9800 ?
    C4 H4B . 0.9800 ?
    C4 H4C . 0.9800 ?
    C5 H5A . 0.9900 ?
    C5 H5B . 0.9900 ?
    C5 C6 . 1.512(4) ?
    C6 H6A . 0.9800 ?
    C6 H6B . 0.9800 ?
    C6 H6C . 0.9800 ?
    C7 H7A . 0.9900 ?
    C7 H7B . 0.9900 ?
    C7 C8 . 1.515(3) ?
    C8 H8A . 0.9800 ?
    C8 H8B . 0.9800 ?
    C8 H8C . 0.9800 ?
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
    C1 O1 H1 . . 114.7 ?
    C2 N1 C3 . . 112.00(18) ?
    C2 N1 C5 . . 107.61(18) ?
    C2 N1 C7 . . 108.91(18) ?
    C3 N1 C5 . . 107.89(19) ?
    C3 N1 C7 . . 109.20(19) ?
    C5 N1 C7 . . 111.24(17) ?
    O1 C1 C2 . . 110.4(2) ?
    O2 C1 O1 . . 125.8(2) ?
    O2 C1 C2 . . 123.7(2) ?
    N1 C2 C1 . . 116.35(19) ?
    N1 C2 H2A . . 108.2 ?
    N1 C2 H2B . . 108.2 ?
    C1 C2 H2A . . 108.2 ?
    C1 C2 H2B . . 108.2 ?
    H2A C2 H2B . . 107.4 ?
    N1 C3 H3A . . 108.5 ?
    N1 C3 H3B . . 108.5 ?
    N1 C3 C4 . . 114.9(2) ?
    H3A C3 H3B . . 107.5 ?
    C4 C3 H3A . . 108.5 ?
    C4 C3 H3B . . 108.5 ?
    C3 C4 H4A . . 109.5 ?
    C3 C4 H4B . . 109.5 ?
    C3 C4 H4C . . 109.5 ?
    H4A C4 H4B . . 109.5 ?
    H4A C4 H4C . . 109.5 ?
    H4B C4 H4C . . 109.5 ?
    N1 C5 H5A . . 108.4 ?
    N1 C5 H5B . . 108.4 ?
    H5A C5 H5B . . 107.5 ?
    C6 C5 N1 . . 115.3(2) ?
    C6 C5 H5A . . 108.4 ?
    C6 C5 H5B . . 108.4 ?
    C5 C6 H6A . . 109.5 ?
    C5 C6 H6B . . 109.5 ?
    C5 C6 H6C . . 109.5 ?
    H6A C6 H6B . . 109.5 ?
    H6A C6 H6C . . 109.5 ?
    H6B C6 H6C . . 109.5 ?
    N1 C7 H7A . . 108.7 ?
    N1 C7 H7B . . 108.7 ?
    H7A C7 H7B . . 107.6 ?
    C8 C7 N1 . . 114.2(2) ?
    C8 C7 H7A . . 108.7 ?
    C8 C7 H7B . . 108.7 ?
    C7 C8 H8A . . 109.5 ?
    C7 C8 H8B . . 109.5 ?
    C7 C8 H8C . . 109.5 ?
    H8A C8 H8B . . 109.5 ?
    H8A C8 H8C . . 109.5 ?
    H8B C8 H8C . . 109.5 ?
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
    O1 C1 C2 N1 . . . . -167.3(2) ?
    O2 C1 C2 N1 . . . . 13.8(4) ?
    C2 N1 C3 C4 . . . . 46.5(3) ?
    C2 N1 C5 C6 . . . . 59.1(3) ?
    C2 N1 C7 C8 . . . . 179.0(2) ?
    C3 N1 C2 C1 . . . . 50.4(3) ?
    C3 N1 C5 C6 . . . . -179.9(2) ?
    C3 N1 C7 C8 . . . . 56.4(3) ?
    C5 N1 C2 C1 . . . . 168.8(2) ?
    C5 N1 C3 C4 . . . . -71.8(3) ?
    C5 N1 C7 C8 . . . . -62.6(3) ?
    C7 N1 C2 C1 . . . . -70.5(3) ?
    C7 N1 C3 C4 . . . . 167.2(2) ?
    C7 N1 C5 C6 . . . . -60.1(3) ?
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 H1 O1 7_655 0.97 1.50 2.457(4) 167 yes
    C3 H3A O2 . 0.99 2.39 2.969(3) 116 yes
    C7 H7B O2 . 0.99 2.39 3.068(3) 125 yes
_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     0.361
_shelx_estimated_absorpt_T_max     0.934
