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#$Date: 2024-12-10 04:51:12 +0200 (Tue, 10 Dec 2024) $
#$Revision: 296811 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/27/2312731.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_2312731
loop_
_publ_author_name
'Hollenwäger, Dirk'
'Bockmair, Valentin'
'Kornath, Andreas J.'
_publ_section_title
;
 The crystal structures of methyl prop-2-ynoate, dimethyl fumarate and
 their protonated species.
;
_journal_coeditor_code           OJ3025
_journal_issue                   1
_journal_name_full
'Acta crystallographica. Section C, Structural chemistry'
_journal_paper_doi               10.1107/S2053229624011653
_journal_volume                  81
_journal_year                    2025
_chemical_formula_iupac          'C4 H5 O2 +, As F6 -'
_chemical_formula_moiety         'C4 H5 O2 +, As F6 -'
_chemical_formula_sum            'C4 H5 As F6 O2'
_chemical_formula_weight         274.00
_chemical_name_systematic
;
(1-Methoxyprop-2-yn-1-ylidene)oxidanium hexafluoroarsenate
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2019/3
_cell_angle_alpha                90
_cell_angle_beta                 91.664(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.9609(5)
_cell_length_b                   8.9319(7)
_cell_length_c                   13.7189(9)
_cell_measurement_reflns_used    1298
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      31.4470
_cell_measurement_theta_min      2.2840
_cell_volume                     852.60(11)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
ORTEP-3 for Windows (Farrugia, 2012)
;
_computing_publication_material
;
PLATON (Spek, 2020)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      111(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9809
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Rigaku Xcalibur Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            4205
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.127
_diffrn_reflns_theta_min         2.722
_diffrn_source_current           40
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    4.055
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2020)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.135
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.146
_refine_diff_density_max         0.872
_refine_diff_density_min         -0.923
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0388
_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)+(0.0444P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0895
_refine_ls_wR_factor_ref         0.0986
_reflns_number_gt                1900
_reflns_number_total             2303
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            oj3025.cif
_cod_data_source_block           III
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2312731
_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   0.121
_shelx_estimated_absorpt_t_max   0.589
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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
As As1 0.55531(4) 0.61946(4) 0.31141(2) 0.02340(12) Uani d 1 . .
F F3 0.3663(2) 0.7351(3) 0.28285(13) 0.0380(5) Uani d 1 . .
F F5 0.5944(3) 0.5983(2) 0.18954(13) 0.0380(5) Uani d 1 . .
F F2 0.5053(3) 0.6364(3) 0.43228(14) 0.0462(6) Uani d 1 . .
O O2 0.0897(3) 0.1533(3) 0.50117(16) 0.0301(5) Uani d 1 . .
O O1 0.1633(3) 0.3569(3) 0.42071(18) 0.0310(5) Uani d 1 . .
F F4 0.7411(3) 0.5020(3) 0.33987(16) 0.0503(6) Uani d 1 . .
F F1 0.3982(3) 0.4674(3) 0.30251(16) 0.0508(6) Uani d 1 . .
F F6 0.7072(3) 0.7683(3) 0.31930(17) 0.0496(6) Uani d 1 . .
C C1 0.1973(4) 0.2223(4) 0.44299(19) 0.0244(6) Uani d 1 . .
C C2 0.3535(4) 0.1383(4) 0.4053(2) 0.0256(6) Uani d 1 . .
C C3 0.4795(4) 0.0709(4) 0.3697(2) 0.0323(7) Uani d 1 . .
H H1 0.580815 0.016719 0.341095 0.039 Uiso calc 1 . .
C C4 -0.0767(4) 0.2351(5) 0.5405(3) 0.0417(9) Uani d 1 . .
H H2A -0.030985 0.324746 0.575262 0.063 Uiso calc 1 . .
H H2B -0.144696 0.170089 0.585530 0.063 Uiso calc 1 . .
H H2C -0.164273 0.264647 0.486657 0.063 Uiso calc 1 . .
H H3 0.235(6) 0.394(5) 0.387(3) 0.047(13) Uiso d 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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
As As 0.0499 2.0058 '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
F6 As1 F4 . . 90.03(12) ?
F6 As1 F3 . . 90.88(11) ?
F4 As1 F3 . . 179.09(11) ?
F6 As1 F2 . . 90.72(11) ?
F4 As1 F2 . . 90.39(11) ?
F3 As1 F2 . . 89.53(10) ?
F6 As1 F5 . . 91.87(11) ?
F4 As1 F5 . . 90.84(10) ?
F3 As1 F5 . . 89.20(9) ?
F2 As1 F5 . . 177.13(10) ?
F6 As1 F1 . . 179.51(12) ?
F4 As1 F1 . . 90.37(13) ?
F3 As1 F1 . . 88.72(12) ?
F2 As1 F1 . . 89.55(11) ?
F5 As1 F1 . . 87.85(10) ?
C1 O2 C4 . . 118.0(3) ?
O1 C1 O2 . . 120.3(3) ?
O1 C1 C2 . . 123.4(3) ?
O2 C1 C2 . . 116.2(3) ?
C3 C2 C1 . . 176.8(3) ?
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
As1 F6 . 1.700(2) ?
As1 F4 . 1.702(2) ?
As1 F3 . 1.7091(19) ?
As1 F2 . 1.7109(19) ?
As1 F5 . 1.7122(18) ?
As1 F1 . 1.746(2) ?
O2 C1 . 1.270(3) ?
O2 C4 . 1.484(4) ?
O1 C1 . 1.261(4) ?
C1 C2 . 1.430(4) ?
C2 C3 . 1.180(4) ?
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
C4 O2 C1 O1 . . . . 0.8(4) ?
C4 O2 C1 C2 . . . . -178.7(3) ?
