#------------------------------------------------------------------------------
#$Date: 2024-08-09 04:46:27 +0300 (Fri, 09 Aug 2024) $
#$Revision: 294065 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/25/2312567.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_2312567
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 +, B F4 -, C8 H9 N1 O1'
_chemical_formula_moiety         'C8 H10 N1 O1 +, B F4 -, C8 H9 N1 O1'
_chemical_formula_sum            'C16 H19 B F4 N2 O2'
_chemical_formula_weight         358.14
_chemical_name_systematic
'N-(1-Hydroxyethylidene)anilinium tetrafluoroborate--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                98.7650(10)
_cell_angle_beta                 98.0340(10)
_cell_angle_gamma                105.9770(10)
_cell_formula_units_Z            2
_cell_length_a                   7.10700(10)
_cell_length_b                   9.53810(10)
_cell_length_c                   13.35920(10)
_cell_measurement_reflns_used    15273
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      71.3120
_cell_measurement_theta_min      3.3900
_cell_volume                     844.555(17)
_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, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_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  0.0260
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16151
_diffrn_reflns_theta_full        70.000
_diffrn_reflns_theta_max         71.497
_diffrn_reflns_theta_min         3.410
_diffrn_source                   'microsource tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.051
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81577
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2023)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_description       fragment
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.498
_refine_diff_density_min         -0.285
_refine_ls_extinction_coef       0.0029(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0361
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0515P)²+0.4180P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.0994
_reflns_number_gt                3204
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ef3058.cif
_cod_data_source_block           ACTHBF4
_cod_database_code               2312567
_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
F F1 0.17479(13) 0.72969(10) 0.15243(6) 0.0363(2) Uani d 1 . .
F F2 0.45003(17) 0.87053(10) 0.26709(8) 0.0523(3) Uani d 1 . .
F F3 0.39396(17) 0.62099(11) 0.22065(8) 0.0468(3) Uani d 1 . .
F F4 0.20689(16) 0.70838(12) 0.32094(7) 0.0468(3) Uani d 1 . .
O O1 0.20732(14) 0.80521(9) 0.80500(6) 0.0217(2) Uani d 1 . .
O O2 0.23624(14) 0.62120(9) 0.66512(6) 0.0219(2) Uani d 1 . .
N N1 0.20551(16) 0.86193(11) 0.97469(8) 0.0180(2) Uani d 1 . .
N N2 0.26024(15) 0.57454(11) 0.49737(8) 0.0173(2) Uani d 1 . .
C C1 0.24994(17) 1.01975(13) 0.98913(9) 0.0178(3) Uani d 1 . .
C C2 0.2341(2) 1.09537(14) 0.90877(10) 0.0236(3) Uani d 1 . .
H H2 0.195142 1.042722 0.839170 0.028 Uiso calc 1 . .
C C3 0.2760(2) 1.24928(15) 0.93179(11) 0.0267(3) Uani d 1 . .
H H3 0.266060 1.301806 0.877286 0.032 Uiso calc 1 . .
C C4 0.3320(2) 1.32715(14) 1.03304(10) 0.0237(3) Uani d 1 . .
H H4 0.359178 1.432192 1.047840 0.028 Uiso calc 1 . .
C C5 0.34800(19) 1.25081(14) 1.11246(10) 0.0230(3) Uani d 1 . .
H H5 0.386573 1.303734 1.181995 0.028 Uiso calc 1 . .
C C6 0.30789(19) 1.09700(14) 1.09096(9) 0.0203(3) Uani d 1 . .
H H6 0.320031 1.044962 1.145575 0.024 Uiso calc 1 . .
C C7 0.18644(18) 0.76409(13) 0.88973(9) 0.0179(3) Uani d 1 . .
C C8 0.1340(2) 0.60302(14) 0.89584(10) 0.0232(3) Uani d 1 . .
H H8A -0.006812 0.553716 0.864800 0.035 Uiso calc 1 . .
H H8B 0.157393 0.593867 0.968273 0.035 Uiso calc 1 . .
H H8C 0.217160 0.555952 0.858443 0.035 Uiso calc 1 . .
C C9 0.24731(17) 0.42074(13) 0.48218(9) 0.0170(2) Uani d 1 . .
C C10 0.25925(19) 0.34282(14) 0.56188(10) 0.0208(3) Uani d 1 . .
H H10 0.275176 0.391188 0.631532 0.025 Uiso calc 1 . .
C C11 0.2475(2) 0.19309(14) 0.53781(10) 0.0233(3) Uani d 1 . .
H H11 0.256422 0.139456 0.591755 0.028 Uiso calc 1 . .
C C12 0.22300(19) 0.12099(14) 0.43664(10) 0.0225(3) Uani d 1 . .
H H12 0.213171 0.018354 0.421188 0.027 Uiso calc 1 . .
C C13 0.21292(19) 0.19988(14) 0.35790(10) 0.0224(3) Uani d 1 . .
H H13 0.196856 0.151079 0.288343 0.027 Uiso calc 1 . .
C C14 0.22618(18) 0.34966(14) 0.38024(9) 0.0196(3) Uani d 1 . .
H H14 0.220859 0.403536 0.326216 0.024 Uiso calc 1 . .
C C15 0.25639(17) 0.66609(13) 0.58175(9) 0.0172(3) Uani d 1 . .
C C16 0.27463(19) 0.82377(13) 0.57439(10) 0.0211(3) Uani d 1 . .
H H16A 0.145435 0.841245 0.576130 0.032 Uiso calc 1 . .
H H16B 0.316262 0.842749 0.509563 0.032 Uiso calc 1 . .
H H16C 0.374149 0.890788 0.632662 0.032 Uiso calc 1 . .
B B1 0.3084(2) 0.73385(16) 0.24067(11) 0.0250(3) Uani d 1 . .
H H1N 0.198(2) 0.8250(19) 1.0289(14) 0.028(4) Uiso d 1 . .
H H2N 0.263(2) 0.6114(18) 0.4426(13) 0.024(4) Uiso d 1 . .
H H1H 0.211(4) 0.732(2) 0.7540(16) 0.100(10) Uiso d 1 . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
F F 0.0727 0.0534 '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'
B B 0.0090 0.0039 '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
C7 O1 H1H . . 114.0(19) ?
C7 N1 C1 . . 129.10(11) ?
C7 N1 H1N . . 114.4(11) ?
C1 N1 H1N . . 116.3(11) ?
C15 N2 C9 . . 129.59(10) ?
C15 N2 H2N . . 115.5(11) ?
C9 N2 H2N . . 114.8(11) ?
C2 C1 C6 . . 120.46(11) ?
C2 C1 N1 . . 123.78(11) ?
C6 C1 N1 . . 115.75(11) ?
C1 C2 C3 . . 119.00(12) ?
C1 C2 H2 . . 120.5 ?
C3 C2 H2 . . 120.5 ?
C4 C3 C2 . . 121.00(12) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
C5 C4 C3 . . 119.53(12) ?
C5 C4 H4 . . 120.2 ?
C3 C4 H4 . . 120.2 ?
C4 C5 C6 . . 120.32(12) ?
C4 C5 H5 . . 119.8 ?
C6 C5 H5 . . 119.8 ?
C1 C6 C5 . . 119.69(11) ?
C1 C6 H6 . . 120.2 ?
C5 C6 H6 . . 120.2 ?
O1 C7 N1 . . 120.94(11) ?
O1 C7 C8 . . 121.04(11) ?
N1 C7 C8 . . 118.00(11) ?
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 ?
C14 C9 C10 . . 120.27(11) ?
C14 C9 N2 . . 115.64(10) ?
C10 C9 N2 . . 124.07(11) ?
C11 C10 C9 . . 118.97(11) ?
C11 C10 H10 . . 120.5 ?
C9 C10 H10 . . 120.5 ?
C12 C11 C10 . . 121.13(12) ?
C12 C11 H11 . . 119.4 ?
C10 C11 H11 . . 119.4 ?
C11 C12 C13 . . 119.45(11) ?
C11 C12 H12 . . 120.3 ?
C13 C12 H12 . . 120.3 ?
C14 C13 C12 . . 120.38(12) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C9 . . 119.78(11) ?
C13 C14 H14 . . 120.1 ?
C9 C14 H14 . . 120.1 ?
O2 C15 N2 . . 121.22(11) ?
O2 C15 C16 . . 121.29(11) ?
N2 C15 C16 . . 117.48(10) ?
C15 C16 H16A . . 109.5 ?
C15 C16 H16B . . 109.5 ?
H16A C16 H16B . . 109.5 ?
C15 C16 H16C . . 109.5 ?
H16A C16 H16C . . 109.5 ?
H16B C16 H16C . . 109.5 ?
F2 B1 F3 . . 111.25(14) ?
F2 B1 F4 . . 110.09(12) ?
F3 B1 F4 . . 107.84(11) ?
F2 B1 F1 . . 109.04(11) ?
F3 B1 F1 . . 108.86(12) ?
F4 B1 F1 . . 109.74(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
F1 B1 . 1.3946(17) ?
F2 B1 . 1.3693(17) ?
F3 B1 . 1.3849(18) ?
F4 B1 . 1.3889(18) ?
O1 C7 . 1.2679(15) ?
O1 H1H . 0.906(10) ?
O2 C15 . 1.2651(15) ?
N1 C7 . 1.3199(16) ?
N1 C1 . 1.4268(15) ?
N1 H1N . 0.854(18) ?
N2 C15 . 1.3251(16) ?
N2 C9 . 1.4253(15) ?
N2 H2N . 0.859(17) ?
C1 C2 . 1.3901(17) ?
C1 C6 . 1.3907(17) ?
C2 C3 . 1.3908(18) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.3857(19) ?
C3 H3 . 0.9500 ?
C4 C5 . 1.3843(19) ?
C4 H4 . 0.9500 ?
C5 C6 . 1.3909(18) ?
C5 H5 . 0.9500 ?
C6 H6 . 0.9500 ?
C7 C8 . 1.4958(17) ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C8 H8C . 0.9800 ?
C9 C14 . 1.3936(17) ?
C9 C10 . 1.3941(17) ?
C10 C11 . 1.3917(17) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.3838(19) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.3884(18) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.3882(17) ?
C13 H13 . 0.9500 ?
C14 H14 . 0.9500 ?
C15 C16 . 1.4931(16) ?
C16 H16A . 0.9800 ?
C16 H16B . 0.9800 ?
C16 H16C . 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 F1 1_556 0.854(18) 2.007(19) 2.8606(13) 177.6(16) yes
N2 H2N F4 . 0.859(17) 2.033(18) 2.8744(14) 166.0(15) yes
O1 H1H O2 . 0.906(10) 1.530(10) 2.4333(12) 174(3) 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 . . . . 16.3(2) ?
C7 N1 C1 C6 . . . . -165.00(12) ?
C6 C1 C2 C3 . . . . -0.3(2) ?
N1 C1 C2 C3 . . . . 178.26(12) ?
C1 C2 C3 C4 . . . . -0.3(2) ?
C2 C3 C4 C5 . . . . 0.5(2) ?
C3 C4 C5 C6 . . . . -0.1(2) ?
C2 C1 C6 C5 . . . . 0.73(19) ?
N1 C1 C6 C5 . . . . -177.98(11) ?
C4 C5 C6 C1 . . . . -0.50(19) ?
C1 N1 C7 O1 . . . . -0.2(2) ?
C1 N1 C7 C8 . . . . -178.57(11) ?
C15 N2 C9 C14 . . . . 170.86(12) ?
C15 N2 C9 C10 . . . . -10.7(2) ?
C14 C9 C10 C11 . . . . -0.71(18) ?
N2 C9 C10 C11 . . . . -179.10(11) ?
C9 C10 C11 C12 . . . . -0.42(19) ?
C10 C11 C12 C13 . . . . 1.0(2) ?
C11 C12 C13 C14 . . . . -0.35(19) ?
C12 C13 C14 C9 . . . . -0.78(19) ?
C10 C9 C14 C13 . . . . 1.31(19) ?
N2 C9 C14 C13 . . . . 179.82(11) ?
C9 N2 C15 O2 . . . . -1.05(19) ?
C9 N2 C15 C16 . . . . 179.57(11) ?
