Salt forms of amides: protonation of acetanilide.
Jaconelli, Harry S.; Kennedy, Alan R.; Acta crystallographica. Section C, Structural chemistry 80 (2024) –; doi:10.1107/S2053229624007332

data_2312568
_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 +, I2 Br1 -, C8 H9 N1 O1, 0.5I2'
_chemical_formula_moiety         'C8 H10 N1 O1 +, I2 Br1 -, C8 H9 N1 O1, 0.5I2'
_chemical_formula_sum            'C16 H19 Br0.93 I3.07 N2 O2'
_chemical_formula_weight         735.18
_chemical_name_systematic
;
<i>N</i>-(1-Hydroxyethylidene)anilinium diiodobromide--\
<i>N</i>-phenylacetamide--diiodine (2/2/1)
;
_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   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 91.970(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.89560(10)
_cell_length_b                   18.6224(4)
_cell_length_c                   19.9632(4)
_cell_measurement_reflns_used    13599
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.4720
_cell_measurement_theta_min      2.3540
_cell_volume                     2190.47(7)
_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_publication_material
;
SHELXL2018 in WinGX (Farrugia, 2012)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015<i>b</i>)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015<i>a</i>)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.984
_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  0.0959
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21645
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         71.536
_diffrn_reflns_theta_min         3.246
_diffrn_source                   'microsource tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    36.463
_exptl_absorpt_correction_T_max  0.164
_exptl_absorpt_correction_T_min  0.014
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
[CrysAlis PRO (Rigaku OD, 2023), based on expressions derived by
Clark & Reid (1995)]
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.229
_exptl_crystal_description       'broken needle'
_exptl_crystal_F_000             1361
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.055
_refine_diff_density_max         1.495
_refine_diff_density_min         -1.862
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         4338
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0516
_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/[\s^2^(Fo^2^)+(0.1066P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1466
_refine_ls_wR_factor_ref         0.1508
_reflns_number_gt                3762
_reflns_number_total             4338
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ef3058.cif
_cod_data_source_block           ACTHI2Br
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               2312568
_shelx_hkl_checksum              26007
_shelx_res_checksum              91624