##############################################################################
#                                                                            #
# This CIF contains the data for a data article accepted for                 #
# publication in IUCrData. It conforms to the requirements of                #
# Notes for Authors for IUCrData, and has been                               #
# peer reviewed under the auspices of IUCrData.                              #
#                                                                            #
# 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 data    # 
# article from which it was obtained.                                        #
#                                                                            #
##############################################################################
data_I
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_journal_date_recd_electronic     2023-08-30
_journal_date_accepted     2023-09-07
_journal_name_full     'IUCrData'
_journal_year     2023
_journal_volume     8
_journal_issue      9
_journal_page_first     0
_journal_page_last     0
_journal_paper_category     HO
_journal_paper_doi     10.1107/S2414314623007848
_journal_coeditor_code     HB4448
_publ_contact_author_name     'Edward Rajaseelan'
_publ_contact_author_address
;
Department of Chemistry, Millersville University, Millersville, PA 17551, USA
;
_publ_contact_author_email     'edward.rajaseelan@millersville.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone     '(717) 871-7395'
_publ_section_title
;
1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Maynard, Aaron' .
;
Department of Chemistry, Millersville University, Millersville, PA 17551,
USA
;
    'Keller, Taylor M.' .
;
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104,
USA
;
    'Gau, Michael' .
;
Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104,
USA
;
    'Albert, Daniel R.' .
;
Department of Chemistry, Millersville University, Millersville, PA 17551,
USA
;
    'Rajaseelan, Edward' .
;
Department of Chemistry, Millersville University, Millersville, PA 17551,
USA
;
_publ_section_synopsis
;
The title compound crystallizes with Z = 6 in space group
P2₁/m.
;
_chemical_name_systematic
;
1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
_chemical_name_common
;
1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
_chemical_formula_moiety     'C7 H14 N3 +, Br -'
_chemical_formula_sum     'C7 H14 Br N3'
_chemical_formula_iupac     'C7 H14 N3 +, Br -'
_chemical_formula_weight     220.12
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21/m '
_space_group_name_Hall     '-P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
    '-x, -y, -z'
    'x, -y-1/2, z'
_cell_length_a     8.1283(2)
_cell_length_b     21.3822(7)
_cell_length_c     8.6376(2)
_cell_angle_alpha     90
_cell_angle_beta     101.713(3)
_cell_angle_gamma     90
_cell_volume     1469.96(7)
_cell_formula_units_Z     6
_cell_measurement_reflns_used     9609
_cell_measurement_theta_min     3.1300
_cell_measurement_theta_max     28.2270
_cell_measurement_temperature     100
_exptl_crystal_description     plate
_exptl_crystal_colour     colourless
_exptl_crystal_size_max     0.38
_exptl_crystal_size_mid     0.25
_exptl_crystal_size_min     0.04
_exptl_crystal_density_diffrn     1.492
_exptl_crystal_F_000     672
_exptl_absorpt_coefficient_mu     4.142
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD; 2022)
;
_exptl_absorpt_correction_T_min     0.48317
_exptl_absorpt_correction_T_max     1.00000
_diffrn_ambient_temperature     100
_diffrn_source     'micro-focus sealed X-ray tube'
_diffrn_radiation_type     'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator     mirror
_diffrn_measurement_device_type     'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_device     'κ-geometry diffractometer'
_diffrn_measurement_method     'ω scans'
_diffrn_detector     'HPC area detector'
_diffrn_detector_area_resol_mean     10.0000
_diffrn_reflns_number     23168
_diffrn_reflns_av_R_equivalents     0.0363
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_theta_min     2.590
_diffrn_reflns_theta_max     28.279
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     0.999
_diffrn_reflns_limit_h_min     -10
_diffrn_reflns_limit_h_max     10
_diffrn_reflns_limit_k_min     -27
_diffrn_reflns_limit_k_max     28
_diffrn_reflns_limit_l_min     -11
_diffrn_reflns_limit_l_max     11
_diffrn_radiation_probe     x-ray
_reflns_number_total     3747
_reflns_number_gt     3142
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0314
_refine_ls_R_factor_gt     0.0224
_refine_ls_wR_factor_gt     0.0494
_refine_ls_wR_factor_ref     0.0516
_refine_ls_goodness_of_fit_ref     1.038
_refine_ls_restrained_S_all     1.038
_refine_ls_number_reflns     3747
_refine_ls_number_parameters     168
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0235P)²+0.2540P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     dual
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.379
_refine_diff_density_min     -0.291
_refine_ls_extinction_method     none
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'
    'Br' 'Br' -0.2901 2.4595
                         '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'
_computing_data_collection
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_cell_refinement
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
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 0.65535(3) 0.750000 0.86475(2) 0.01997(6) Uani d 1 . .
    Br Br2 0.36575(2) 0.58378(2) 1.16793(2) 0.01912(5) Uani d 1 . .
    N N1 0.5536(2) 0.750000 0.34816(19) 0.0180(4) Uani d 1 . .
    N N2 0.3012(2) 0.750000 0.22004(19) 0.0181(4) Uani d 1 . .
    N N3 0.2904(2) 0.750000 0.3756(2) 0.0225(4) Uani d 1 . .
    C C1 0.4576(3) 0.750000 0.2031(2) 0.0175(4) Uani d 1 . .
    H H1 0.495511 0.750000 0.106069 0.021 Uiso calc 1 . .
    C C2 0.4471(3) 0.750000 0.4505(2) 0.0209(4) Uani d 1 . .
    H H2 0.482097 0.750000 0.562368 0.025 Uiso calc 1 . .
    C C3 0.7407(3) 0.750000 0.3888(3) 0.0277(5) Uani d 1 . .
    H H3 0.777584 0.750000 0.506529 0.033 Uiso calc 1 . .
    C C4 0.8056(2) 0.80896(8) 0.3239(2) 0.0324(4) Uani d 1 . .
    H H4A 0.772489 0.809040 0.208337 0.049 Uiso calc 1 . .
    H H4B 0.928441 0.810248 0.355041 0.049 Uiso calc 1 . .
    H H4C 0.757925 0.845690 0.366538 0.049 Uiso calc 1 . .
    C C5 0.1468(3) 0.750000 0.0987(3) 0.0315(6) Uani d 1 . .
    H H5A 0.079611 0.787411 0.112921 0.038 Uiso calc 0.5 . .
    H H5B 0.079611 0.712589 0.112921 0.038 Uiso calc 0.5 . .
    C C6 0.1791(3) 0.750000 -0.0638(3) 0.0353(6) Uani d 1 . .
    H H6A 0.225946 0.790528 -0.085598 0.053 Uiso calc 0.5 A -1
    H H6B 0.073605 0.742719 -0.139517 0.053 Uiso calc 0.5 A -1
    H H6C 0.259308 0.716754 -0.073790 0.053 Uiso calc 0.5 A -1
    N N4 0.45707(16) 0.58697(5) 0.70657(14) 0.0163(3) Uani d 1 . .
    N N5 0.71989(15) 0.59178(5) 0.80363(14) 0.0170(3) Uani d 1 . .
    N N6 0.70540(17) 0.59818(6) 0.64405(15) 0.0234(3) Uani d 1 . .
    C C7 0.5439(2) 0.59462(7) 0.58810(18) 0.0223(3) Uani d 1 . .
    H H7 0.493358 0.597046 0.478994 0.027 Uiso calc 1 . .
    C C8 0.57173(19) 0.58536(6) 0.84100(17) 0.0167(3) Uani d 1 . .
    H H8 0.550409 0.580476 0.944460 0.020 Uiso calc 1 . .
    C C9 0.27440(18) 0.57739(7) 0.69275(18) 0.0198(3) Uani d 1 . .
    H H9 0.249096 0.576878 0.801314 0.024 Uiso calc 1 . .
    C C10 0.1780(2) 0.63095(8) 0.6001(2) 0.0296(4) Uani d 1 . .
    H H10A 0.218468 0.670794 0.649669 0.044 Uiso calc 1 . .
    H H10B 0.057966 0.626396 0.599636 0.044 Uiso calc 1 . .
    H H10C 0.195525 0.630178 0.491108 0.044 Uiso calc 1 . .
    C C11 0.2264(2) 0.51438(8) 0.61529(19) 0.0287(4) Uani d 1 . .
    H H11A 0.240093 0.515644 0.505186 0.043 Uiso calc 1 . .
    H H11B 0.109054 0.505046 0.618208 0.043 Uiso calc 1 . .
    H H11C 0.299190 0.481809 0.672508 0.043 Uiso calc 1 . .
    C C12 0.88457(19) 0.59542(8) 0.9095(2) 0.0242(3) Uani d 1 . .
    H H12A 0.917169 0.639848 0.927513 0.029 Uiso calc 1 . .
    H H12B 0.969276 0.574799 0.859048 0.029 Uiso calc 1 . .
    C C13 0.8832(2) 0.56445(8) 1.06588(18) 0.0246(3) Uani d 1 . .
    H H13A 0.847326 0.520823 1.048013 0.037 Uiso calc 1 . .
    H H13B 0.804907 0.586585 1.119266 0.037 Uiso calc 1 . .
    H H13C 0.996325 0.565779 1.132088 0.037 Uiso calc 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
    N1 C1 . 1.335(2) ?
    N1 C2 . 1.357(3) ?
    N1 C3 . 1.490(3) ?
    N2 N3 . 1.364(2) ?
    N2 C1 . 1.308(3) ?
    N2 C5 . 1.463(3) ?
    N3 C2 . 1.307(3) ?
    C3 C4 . 1.517(2) ?
    C3 C4 4_575 1.517(2) ?
    C5 C6 . 1.480(3) ?
    N4 C7 . 1.366(2) ?
    N4 C8 . 1.3337(19) ?
    N4 C9 . 1.4795(19) ?
    N5 N6 . 1.3662(18) ?
    N5 C8 . 1.316(2) ?
    N5 C12 . 1.4618(19) ?
    N6 C7 . 1.305(2) ?
    C9 C10 . 1.520(2) ?
    C9 C11 . 1.520(2) ?
    C12 C13 . 1.507(2) ?
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 N1 C2 . . 106.43(18) ?
    C1 N1 C3 . . 126.56(18) ?
    C2 N1 C3 . . 127.01(17) ?
    N3 N2 C5 . . 119.20(18) ?
    C1 N2 N3 . . 111.63(16) ?
    C1 N2 C5 . . 129.18(18) ?
    C2 N3 N2 . . 103.67(18) ?
    N2 C1 N1 . . 106.93(18) ?
    N3 C2 N1 . . 111.35(18) ?
    N1 C3 C4 . 4_575 109.14(11) ?
    N1 C3 C4 . . 109.14(11) ?
    C4 C3 C4 . 4_575 112.4(2) ?
    N2 C5 C6 . . 112.79(19) ?
    C7 N4 C9 . . 128.25(12) ?
    C8 N4 C7 . . 106.21(13) ?
    C8 N4 C9 . . 125.39(13) ?
    N6 N5 C12 . . 120.41(13) ?
    C8 N5 N6 . . 111.24(12) ?
    C8 N5 C12 . . 128.29(13) ?
    C7 N6 N5 . . 104.00(13) ?
    N6 C7 N4 . . 111.31(13) ?
    N5 C8 N4 . . 107.24(13) ?
    N4 C9 C10 . . 109.85(12) ?
    N4 C9 C11 . . 108.78(12) ?
    C11 C9 C10 . . 112.16(13) ?
    N5 C12 C13 . . 111.39(13) ?
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
    N2 N3 C2 N1 . . . . 0.000000 ?
    N3 N2 C1 N1 . . . . 0.000000 ?
    N3 N2 C5 C6 . . . . 180.000000 ?
    C1 N1 C2 N3 . . . . 0.000000 ?
    C1 N1 C3 C4 . . . 4_575 -61.59(13) ?
    C1 N1 C3 C4 . . . . 61.59(13) ?
    C1 N2 N3 C2 . . . . 0.000000 ?
    C1 N2 C5 C6 . . . . 0.000000 ?
    C2 N1 C1 N2 . . . . 0.000000 ?
    C2 N1 C3 C4 . . . 4_575 118.41(13) ?
    C2 N1 C3 C4 . . . . -118.41(13) ?
    C3 N1 C1 N2 . . . . 180.000000 ?
    C3 N1 C2 N3 . . . . 180.000000 ?
    C5 N2 N3 C2 . . . . 180.000000 ?
    C5 N2 C1 N1 . . . . 180.000000 ?
    N5 N6 C7 N4 . . . . 0.69(16) ?
    N6 N5 C8 N4 . . . . 0.42(15) ?
    N6 N5 C12 C13 . . . . -158.90(13) ?
    C7 N4 C8 N5 . . . . 0.01(15) ?
    C7 N4 C9 C10 . . . . -56.70(19) ?
    C7 N4 C9 C11 . . . . 66.41(18) ?
    C8 N4 C7 N6 . . . . -0.46(16) ?
    C8 N4 C9 C10 . . . . 128.34(14) ?
    C8 N4 C9 C11 . . . . -108.55(15) ?
    C8 N5 N6 C7 . . . . -0.69(16) ?
    C8 N5 C12 C13 . . . . 24.4(2) ?
    C9 N4 C7 N6 . . . . -176.18(13) ?
    C9 N4 C8 N5 . . . . 175.89(12) ?
    C12 N5 N6 C7 . . . . -177.94(13) ?
    C12 N5 C8 N4 . . . . 177.41(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_D
    _geom_hbond_site_symmetry_H
    _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
    C1 H1 Br1 . . 1_554 0.95 2.67 3.610(2) 170 yes
    C2 H2 Br2 . . 1_554 0.95 2.70 3.6344(18) 166 yes
    C7 H7 Br2 . . 1_554 0.95 2.69 3.6316(15) 170 yes
    C8 H8 Br2 . . 1_554 0.95 2.68 3.5635(15) 156 yes
