#------------------------------------------------------------------------------
#$Date: 2015-05-16 04:56:37 +0300 (Sat, 16 May 2015) $
#$Revision: 136635 $
#$URL: svn://www.crystallography.net/cod/cif/2/24/06/2240695.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_2240695
loop_
_publ_author_name
'Guino-o, Marites A.'
'Talbot, Meghan O.'
'Slitts, Michael M.'
'Pham, Theresa N.'
'Audi, Maya C.'
'Janzen, Daron E.'
_publ_section_title
;
 Crystal structures of five 1-alkyl-4-aryl-1,2,4-triazol-1-ium halide
 salts
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              628
_journal_page_last               635
_journal_paper_doi               10.1107/S2056989015009019
_journal_volume                  71
_journal_year                    2015
_chemical_formula_iupac          'C12 H16 N3 +, I -'
_chemical_formula_moiety         'C12 H16 N3 +, I -'
_chemical_formula_sum            'C12 H16 I N3'
_chemical_formula_weight         329.18
_chemical_name_systematic
;
1-Isopropyl-4-(4-methylphenyl)-1,2,4-triazol-1-ium iodide
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_Hall           '-P 2ab 2ac'
_space_group_name_H-M_alt        'P c c n'
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.843(3)
_cell_length_b                   21.933(4)
_cell_length_c                   7.8250(14)
_cell_measurement_reflns_used    12738
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.43
_cell_measurement_theta_min      3.05
_cell_volume                     2719.1(9)
_computing_cell_refinement
;
CrystalClearSM Expert (Rigaku, 2011)
;
_computing_data_collection
;
CrystalClearSM Expert (Rigaku, 2011)
;
_computing_data_reduction
;
CrystalClearSM Expert (Rigaku, 2011)
;
_computing_molecular_graphics
;
CrystalStructure (Rigaku, 2010)
;
_computing_publication_material
;
Mercury (Macrae et al., 2006)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SIR97 (Altomare et al., 1999)
;
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 6.849
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            16099
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.362
_diffrn_reflns_theta_min         3.048
_exptl_absorpt_coefficient_mu    2.335
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_correction_T_min  0.564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(REQAB; Rigaku, 1998)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.608
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.430
_refine_diff_density_min         -0.362
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0305
_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)+(0.0241P)²+1.7237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0600
_refine_ls_wR_factor_ref         0.0648
_reflns_number_gt                2150
_reflns_number_total             2767
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zl2623sup1.cif
_cod_data_source_block           salt2
_cod_original_cell_volume        2719.0(8)
_cod_database_code               2240695
_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   0.376
_shelx_estimated_absorpt_t_max   0.912
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, z+1/2'
'x, -y+1/2, z+1/2'
'-x+1/2, -y+1/2, z'
'-x, -y, -z'
'x-1/2, -y, -z-1/2'
'-x, y-1/2, -z-1/2'
'x-1/2, 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
I I1 0.39750(2) 0.11566(2) 0.28064(3) 0.03506(9) Uani d 1
N N1 0.36095(16) 0.01570(12) 0.6774(4) 0.0323(7) Uani d 1
N N2 0.40416(16) 0.10301(12) 0.7635(4) 0.0323(7) Uani d 1
N N3 0.47092(18) 0.06448(14) 0.7832(4) 0.0474(8) Uani d 1
C C1 0.3387(2) 0.07437(14) 0.7003(4) 0.0327(8) Uani d 1
H H1 0.2852 0.0918 0.6752 0.039 Uiso calc 1
C C2 0.4431(2) 0.01195(17) 0.7293(5) 0.0466(10) Uani d 1
H H2 0.4758 -0.0243 0.7266 0.056 Uiso calc 1
C C3 0.4142(2) 0.16834(15) 0.8098(5) 0.0360(8) Uani d 1
H H3 0.4272 0.1708 0.9347 0.043 Uiso calc 1
C C4 0.3329(2) 0.20152(16) 0.7779(6) 0.0558(12) Uani d 1
H H4A 0.2877 0.1826 0.8450 0.067 Uiso calc 1
H H4B 0.3188 0.1993 0.6561 0.067 Uiso calc 1
H H4C 0.3391 0.2443 0.8117 0.067 Uiso calc 1
C C5 0.4878(2) 0.19528(16) 0.7123(5) 0.0483(10) Uani d 1
H H5A 0.4763 0.1933 0.5894 0.058 Uiso calc 1
H H5B 0.5392 0.1721 0.7379 0.058 Uiso calc 1
H H5C 0.4958 0.2379 0.7465 0.058 Uiso calc 1
C C6 0.3098(2) -0.03293(14) 0.6067(4) 0.0335(8) Uani d 1
C C7 0.3493(2) -0.08364(16) 0.5362(5) 0.0417(9) Uani d 1
H H7 0.4090 -0.0858 0.5296 0.050 Uiso calc 1
C C8 0.3000(2) -0.13047(15) 0.4763(5) 0.0449(10) Uani d 1
H H8 0.3269 -0.1655 0.4301 0.054 Uiso calc 1
C C9 0.2121(2) -0.12853(15) 0.4805(5) 0.0387(9) Uani d 1
C C10 0.1751(2) -0.07632(15) 0.5485(5) 0.0401(9) Uani d 1
H H10 0.1153 -0.0731 0.5506 0.048 Uiso calc 1
C C11 0.2231(2) -0.02902(14) 0.6130(5) 0.0377(9) Uani d 1
H H11 0.1966 0.0058 0.6612 0.045 Uiso calc 1
C C12 0.1601(3) -0.18091(17) 0.4159(6) 0.0535(11) Uani d 1
H H12A 0.1066 -0.1655 0.3703 0.064 Uiso calc 1
H H12B 0.1487 -0.2093 0.5099 0.064 Uiso calc 1
H H12C 0.1910 -0.2022 0.3252 0.064 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.4742 1.8119 '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'
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 105.5(3)
C1 N1 C6 127.5(3)
C2 N1 C6 127.0(3)
C1 N2 N3 111.1(3)
C1 N2 C3 129.7(3)
N3 N2 C3 119.1(3)
C2 N3 N2 104.4(3)
N2 C1 N1 107.5(3)
N2 C1 H1 126.2
N1 C1 H1 126.2
N3 C2 N1 111.4(3)
N3 C2 H2 124.3
N1 C2 H2 124.3
N2 C3 C4 109.6(3)
N2 C3 C5 109.6(3)
C4 C3 C5 112.8(3)
N2 C3 H3 108.2
C4 C3 H3 108.2
C5 C3 H3 108.2
C3 C4 H4A 109.5
C3 C4 H4B 109.5
H4A C4 H4B 109.5
C3 C4 H4C 109.5
H4A C4 H4C 109.5
H4B C4 H4C 109.5
C3 C5 H5A 109.5
C3 C5 H5B 109.5
H5A C5 H5B 109.5
C3 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C11 C6 C7 120.8(3)
C11 C6 N1 119.9(3)
C7 C6 N1 119.3(3)
C8 C7 C6 118.6(3)
C8 C7 H7 120.7
C6 C7 H7 120.7
C7 C8 C9 122.5(3)
C7 C8 H8 118.8
C9 C8 H8 118.8
C10 C9 C8 117.1(3)
C10 C9 C12 121.8(3)
C8 C9 C12 121.1(3)
C11 C10 C9 121.6(3)
C11 C10 H10 119.2
C9 C10 H10 119.2
C6 C11 C10 119.3(3)
C6 C11 H11 120.3
C10 C11 H11 120.3
C9 C12 H12A 109.5
C9 C12 H12B 109.5
H12A C12 H12B 109.5
C9 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.346(4)
N1 C2 1.365(4)
N1 C6 1.449(4)
N2 C1 1.310(4)
N2 N3 1.363(4)
N2 C3 1.487(4)
N3 C2 1.304(5)
C1 H1 0.9500
C2 H2 0.9500
C3 C4 1.500(5)
C3 C5 1.514(5)
C3 H3 1.0000
C4 H4A 0.9800
C4 H4B 0.9800
C4 H4C 0.9800
C5 H5A 0.9800
C5 H5B 0.9800
C5 H5C 0.9800
C6 C11 1.377(4)
C6 C7 1.390(4)
C7 C8 1.372(5)
C7 H7 0.9500
C8 C9 1.394(5)
C8 H8 0.9500
C9 C10 1.392(5)
C9 C12 1.502(5)
C10 C11 1.383(5)
C10 H10 0.9500
C11 H11 0.9500
C12 H12A 0.9800
C12 H12B 0.9800
C12 H12C 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
C1 H1 I1 2 0.95 3.06 3.901(3) 149.1
C2 H2 I1 5_656 0.95 2.84 3.771(4) 168.0
C3 H3 I1 1_556 1.00 3.00 3.870(4) 145.8
C11 H11 I1 2 0.95 2.98 3.930(3) 174.2
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
C1 N2 N3 C2 0.1(4)
C3 N2 N3 C2 -178.7(3)
N3 N2 C1 N1 0.3(4)
C3 N2 C1 N1 178.9(3)
C2 N1 C1 N2 -0.5(4)
C6 N1 C1 N2 -178.4(3)
N2 N3 C2 N1 -0.4(4)
C1 N1 C2 N3 0.6(4)
C6 N1 C2 N3 178.6(3)
C1 N2 C3 C4 1.5(5)
N3 N2 C3 C4 -179.9(3)
C1 N2 C3 C5 -122.8(4)
N3 N2 C3 C5 55.8(4)
C1 N1 C6 C11 -24.1(5)
C2 N1 C6 C11 158.4(4)
C1 N1 C6 C7 157.1(3)
C2 N1 C6 C7 -20.4(5)
C11 C6 C7 C8 -1.4(5)
N1 C6 C7 C8 177.3(3)
C6 C7 C8 C9 1.3(6)
C7 C8 C9 C10 0.2(6)
C7 C8 C9 C12 -179.2(4)
C8 C9 C10 C11 -1.6(6)
C12 C9 C10 C11 177.9(4)
C7 C6 C11 C10 0.1(5)
N1 C6 C11 C10 -178.6(3)
C9 C10 C11 C6 1.4(6)

_cod_database_fobs_code 2240695
