#------------------------------------------------------------------------------
#$Date: 2024-08-09 04:46:27 +0300 (Fri, 09 Aug 2024) $
#$Revision: 294065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312566.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_2312566
loop_
_publ_author_name
'Jaconelli, Harry S.'
'Kennedy, Alan R.'
_publ_section_title
;
 Salt forms of amides: protonation of acetanilide.
;
_journal_coeditor_code           EF3058
_journal_issue                   9
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624007332
_journal_volume                  80
_journal_year                    2024
_chemical_formula_iupac          'C8 H10 N1 O1 +, I3 -, C8 H9 N1 O1'
_chemical_formula_moiety         'C8 H10 N1 O1 +, I3 -, C8 H9 N1 O1'
_chemical_formula_sum            'C16 H19 I3 N2 O2'
_chemical_formula_weight         652.03
_chemical_name_systematic
;
N-(1-Hydroxyethylidene)anilinium triiodide--N-phenylacetamide
(1/1)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                113.612(2)
_cell_angle_beta                 103.144(2)
_cell_angle_gamma                104.263(3)
_cell_formula_units_Z            1
_cell_length_a                   7.3766(2)
_cell_length_b                   8.8131(3)
_cell_length_c                   9.3226(2)
_cell_measurement_reflns_used    6490
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.1280
_cell_measurement_theta_min      5.5200
_cell_volume                     500.61(3)
_computing_cell_refinement
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_data_collection
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_data_reduction
;
Crysalis PRO (Rigaku OD, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
SHELXL2018 in WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'Rigaku Synergy-i'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7238
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         71.347
_diffrn_reflns_theta_min         5.568
_diffrn_source                   'microsource tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    36.856
_exptl_absorpt_correction_T_max  0.480
_exptl_absorpt_correction_T_min  0.034
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    2.163
_exptl_crystal_description       needle
_exptl_crystal_F_000             304
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.235
_refine_diff_density_min         -1.789
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1900
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.102
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0375
_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)+(0.0828P)²+0.0507P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1071
_reflns_number_gt                1846
_reflns_number_total             1900
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3058.cif
_cod_data_source_block           ACTHI3
_cod_database_code               2312566
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
I I1 0.55941(4) 0.66145(3) 0.88696(3) 0.02516(16) Uani d 1 . .
I I2 0.500000 1.000000 1.000000 0.02257(17) Uani d 1 . .
O O1 0.1752(4) 0.0806(4) 0.5302(4) 0.0272(6) Uani d 1 . .
N N1 0.3915(5) 0.2177(5) 0.4434(4) 0.0241(7) Uani d 1 . .
C C1 0.5812(6) 0.2611(5) 0.5644(5) 0.0246(8) Uani d 1 . .
C C2 0.6054(7) 0.2189(6) 0.6934(6) 0.0276(9) Uani d 1 . .
H H2 0.491090 0.154855 0.705554 0.033 Uiso calc 1 . .
C C3 0.7970(7) 0.2704(6) 0.8050(5) 0.0271(9) Uani d 1 . .
H H3 0.812915 0.242810 0.894584 0.033 Uiso calc 1 . .
C C4 0.9670(7) 0.3625(6) 0.7877(5) 0.0283(9) Uani d 1 . .
H H4 1.098103 0.395625 0.863205 0.034 Uiso calc 1 . .
C C5 0.9405(8) 0.4045(7) 0.6575(6) 0.0325(10) Uani d 1 . .
H H5 1.054485 0.468933 0.645208 0.039 Uiso calc 1 . .
C C6 0.7492(7) 0.3533(6) 0.5454(6) 0.0282(9) Uani d 1 . .
H H6 0.732544 0.381001 0.455922 0.034 Uiso calc 1 . .
C C7 0.2071(6) 0.1329(5) 0.4278(5) 0.0239(8) Uani d 1 . .
C C8 0.0359(6) 0.1033(6) 0.2834(5) 0.0289(9) Uani d 1 . .
H H8A -0.040316 -0.025349 0.209444 0.043 Uiso calc 1 . .
H H8B 0.089110 0.156041 0.219639 0.043 Uiso calc 1 . .
H H8C -0.052750 0.159959 0.326851 0.043 Uiso calc 1 . .
H H1N 0.401(9) 0.244(7) 0.363(5) 0.035(14) Uiso d 1 . .
H H1H 0.049(7) 0.027(17) 0.514(18) 0.03(3) Uiso d 0.5 A -1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
I I -0.3257 6.8362 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
I1 I2 I1 . 2_677 180.0 ?
C7 O1 H1H . . 117(9) ?
C7 N1 C1 . . 129.7(4) ?
C7 N1 H1N . . 116(4) ?
C1 N1 H1N . . 114(4) ?
C2 C1 C6 . . 120.1(4) ?
C2 C1 N1 . . 124.9(4) ?
C6 C1 N1 . . 115.1(4) ?
C1 C2 C3 . . 119.8(4) ?
C1 C2 H2 . . 120.1 ?
C3 C2 H2 . . 120.1 ?
C2 C3 C4 . . 120.9(4) ?
C2 C3 H3 . . 119.5 ?
C4 C3 H3 . . 119.5 ?
C5 C4 C3 . . 118.7(4) ?
C5 C4 H4 . . 120.7 ?
C3 C4 H4 . . 120.7 ?
C6 C5 C4 . . 120.6(4) ?
C6 C5 H5 . . 119.7 ?
C4 C5 H5 . . 119.7 ?
C5 C6 C1 . . 119.9(4) ?
C5 C6 H6 . . 120.0 ?
C1 C6 H6 . . 120.0 ?
O1 C7 N1 . . 121.7(4) ?
O1 C7 C8 . . 121.0(4) ?
N1 C7 C8 . . 117.3(4) ?
C7 C8 H8A . . 109.5 ?
C7 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
C7 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
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
I1 I2 . 2.9224(3) ?
O1 C7 . 1.257(5) ?
O1 H1H . 0.880(10) ?
N1 C7 . 1.324(6) ?
N1 C1 . 1.432(5) ?
N1 H1N . 0.877(10) ?
C1 C2 . 1.381(6) ?
C1 C6 . 1.395(6) ?
C2 C3 . 1.387(6) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.398(6) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.392(6) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.387(6) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.503(6) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 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
_geom_hbond_publ_flag
N1 H1N I1 2_666 0.877(10) 2.824(11) 3.700(3) 178(5) yes
O1 H1H O1 2_556 0.880(10) 1.552(17) 2.430(6) 175(15) 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
C7 N1 C1 C2 . . . . 0.1(7) ?
C7 N1 C1 C6 . . . . -179.7(4) ?
C6 C1 C2 C3 . . . . 0.8(6) ?
N1 C1 C2 C3 . . . . -179.0(4) ?
C1 C2 C3 C4 . . . . -1.0(7) ?
C2 C3 C4 C5 . . . . 1.1(7) ?
C3 C4 C5 C6 . . . . -1.1(7) ?
C4 C5 C6 C1 . . . . 1.0(7) ?
C2 C1 C6 C5 . . . . -0.8(7) ?
N1 C1 C6 C5 . . . . 179.0(4) ?
C1 N1 C7 O1 . . . . 2.3(7) ?
C1 N1 C7 C8 . . . . -178.5(4) ?
