#------------------------------------------------------------------------------
#$Date: 2025-07-05 13:10:14 +0300 (Sat, 05 Jul 2025) $
#$Revision: 300370 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/98/1569883.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_1569883
loop_
_publ_author_name
'Maynard, Aaron'
'Keller, Taylor M.'
'Gau, Michael'
'Albert, Daniel R.'
'Rajaseelan, Edward'
_publ_section_title
;
 1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
_journal_coeditor_code           HB4448
_journal_issue                   9
_journal_name_full               IUCrData
_journal_page_first              x230784
_journal_paper_doi               10.1107/S2414314623007848
_journal_volume                  8
_journal_year                    2023
_chemical_formula_iupac          'C7 H14 N3 +, Br -'
_chemical_formula_moiety         'C7 H14 N3 +, Br -'
_chemical_formula_sum            'C7 H14 Br N3'
_chemical_formula_weight         220.12
_chemical_name_common
;
1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
_chemical_name_systematic
;
1-Ethyl-4-isopropyl-1,2,4-triazolium bromide
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.713(3)
_cell_angle_gamma                90
_cell_formula_units_Z            6
_cell_length_a                   8.1283(2)
_cell_length_b                   21.3822(7)
_cell_length_c                   8.6376(2)
_cell_measurement_reflns_used    9609
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.2270
_cell_measurement_theta_min      3.1300
_cell_volume                     1469.96(7)
_computing_cell_refinement
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlisPro 1.171.42.79a (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.3 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-S'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0363
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            23168
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_min         2.590
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    4.142
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD; 2022)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.379
_refine_diff_density_min         -0.291
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         3747
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0314
_refine_ls_R_factor_gt           0.0224
_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)+(0.0235P)²+0.2540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0494
_refine_ls_wR_factor_ref         0.0516
_reflns_number_gt                3142
_reflns_number_total             3747
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4448.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/m '
_cod_database_code               1569883
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'
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_
_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'
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_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_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
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) ?
